WorldWideScience

Sample records for surfactant alkyl chains

  1. Novel Pyridinium Surfactants with Unsaturated Alkyl Chains : Aggregation Behavior and Interactions with Methyl Orange in Aqueous Solution

    NARCIS (Netherlands)

    Kuiper, Johanna M.; Buwalda, Rixt T.; Hulst, Ron; Engberts, Jan B.F.N.

    2001-01-01

    This paper presents the synthesis and a study of the aggregation behavior of 4-undecyl-1-methyl- and 4-undecenyl-1-methylpyridinium iodide surfactants. The effect of the position of the double bond in the alkyl chain of the surfactant on the critical micelle concentration (cmc), degree of counterion

  2. Theoretical model to investigate the alkyl chain and anion dependent interactions of gemini surfactant with bovine serum albumin.

    Science.gov (United States)

    Vishvakarma, Vijay K; Kumari, Kamlesh; Patel, Rajan; Dixit, V S; Singh, Prashant; Mehrotra, Gopal K; Chandra, Ramesh; Chakrawarty, Anand Kumar

    2015-05-15

    Surfactants are used to prevent the irreversible aggregation of partially refolded proteins and they also assist in protein refolding. We have reported the design and screening of gemini surfactant to stabilize bovine serum albumin (BSA) with the help of computational tool (iGEMDOCK). A series of gemini surfactant has been designed based on bis-N-alkyl nicotinate dianion via varying the alkyl group and anion. On changing the alkyl group and anion of the surfactant, the value of Log P changes means polarity of surfactant can be tuned. Further, the virtual screening of the gemini surfactant has been carried out based on generic evolutionary method. Herein, thermodynamic data was studied to determine the potential of gemini surfactant as BSA stabilizer. Computational tools help to find out the efficient gemini surfactant to stabilize the BSA rather than to use the surfactant randomly and directionless for the stabilization. It can be confirmed through the experimental techniques. Previously, researcher synthesized one of the designed and used gemini surfactant to stabilize the BSA and their interactions were confirmed through various techniques and computational docking. But herein, the authors find the most competent gemini surfactant to stabilize BSA using computational tools on the basis of energy score. Different from the single chain surfactant, the gemini surfactants exhibit much stronger electrostatic and hydrophobic interactions with the protein and are thus effective at much lower concentrations. Based on the present study, it is expected that gemini surfactants may prove useful in the protein stabilization operations and may thus be effectively employed to circumvent the problem of misfolding and aggregation.

  3. Effect of surfactant alkyl chain length on the dispersion, and thermal and dynamic mechanical properties of LDPE/organo-LDH composites

    Directory of Open Access Journals (Sweden)

    2011-05-01

    Full Text Available Low density polyethylene/layered double hydroxide (LDH composites were prepared via melt compounding using different kinds of organo-LDHs and polyethylene-grafted maleic anhydride as the compatibilizer. The organo-LDHs were successfully prepared by converting a commercial MgAl-carbonate LDH into a MgAl-nitrate LDH, which was later modified by anion exchange with linear and branched sodium alkyl sulfates having different alkyl chain lengths (nc = 6, 12 and 20. It was observed that, depending on the size of the surfactant alkyl chain, different degrees of polymer chain intercalation were achieved, which is a function of the interlayer distance of the organo-LDHs, of the packing level of the alkyl chains, and of the different interaction levels between the surfactant and the polymer chains. In particular, when the number of carbon atoms of the surfactant alkyl chain is larger than 12, the intercalation of polymer chains in the interlayer space and depression of the formation of large aggregates of organo-LDH platelets are favored. A remarkable improvement of the thermal-oxidative degradation was evidenced for all of the composites; whereas only a slight increase of the crystallization temperature and no significant changes of both melting temperature and degree of crystallinity were achieved. By thermodynamic mechanical analysis, it was evidenced that a softening of the matrix is may be due to the plasticizing effect of the surfactant.

  4. The Branched-Chain Dodecylbenzene Sulfonate Degradation Pathway of Pseudomonas aeruginosa W51D Involves a Novel Route for Degradation of the Surfactant Lateral Alkyl Chain

    OpenAIRE

    Campos-García, Jesús; Esteve, Abraham; Vázquez-Duhalt, Rafael; Ramos, Juán Luis; Soberón-Chávez, Gloria

    1999-01-01

    Pseudomonas aeruginosa W51D is able to grow by using branched-chain dodecylbenzene sulfonates (B-DBS) or the terpenic alcohol citronellol as a sole source of carbon. A mutant derived from this strain (W51M1) is unable to degrade citronellol but still grows on B-DBS, showing that the citronellol degradation route is not the main pathway involved in the degradation of the surfactant alkyl moiety. The structures of the main B-DBS isomers and of some intermediates were identified by gas chromatog...

  5. The Branched-Chain Dodecylbenzene Sulfonate Degradation Pathway of Pseudomonas aeruginosa W51D Involves a Novel Route for Degradation of the Surfactant Lateral Alkyl Chain

    Science.gov (United States)

    Campos-García, Jesús; Esteve, Abraham; Vázquez-Duhalt, Rafael; Ramos, Juán Luis; Soberón-Chávez, Gloria

    1999-01-01

    Pseudomonas aeruginosa W51D is able to grow by using branched-chain dodecylbenzene sulfonates (B-DBS) or the terpenic alcohol citronellol as a sole source of carbon. A mutant derived from this strain (W51M1) is unable to degrade citronellol but still grows on B-DBS, showing that the citronellol degradation route is not the main pathway involved in the degradation of the surfactant alkyl moiety. The structures of the main B-DBS isomers and of some intermediates were identified by gas chromatography-mass spectrometric analysis, and a possible catabolic route is proposed. PMID:10427075

  6. Effect of alkyl chain asymmetry on catanionic mixtures of hydrogenated and fluorinated surfactants.

    Science.gov (United States)

    Blanco, Elena; Rodriguez-Abreu, Carlos; Schulz, Pablo; Ruso, Juan M

    2010-01-15

    In this work we studied and compared the physicochemical properties of the catanionic mixtures cetyltrimethyl-ammonium bromide-sodium dodecanoate, cetyltrimethyl-ammonium bromide-sodium perfluorodacanoate, octyltrimethylammonium bromide-sodium perfluorodacanoate and cetyltrimethyl-ammonium bromide-sodium octanoate by a combination of rheological, transmission electron microscopy (TEM) and polarized optical microscopy measurements. The binary mixtures of the surfactants have been analyzed at different mixed ratios and total concentration of the mixture. Mixtures containing a perfluorinated surfactant are able to form lamellar liquid crystals and stable spontaneous vesicles. Meanwhile, system containing just hydrogenated surfactants form hexagonal phases or they are arranged in elongated aggregates.

  7. In vitro analysis of the effect of alkyl-chain length of anionic surfactants on the skin by using a reconstructed human epidermal model.

    Science.gov (United States)

    Yamaguchi, Fumiko; Watanabe, Shin-Ichi; Harada, Fusae; Miyake, Miyuki; Yoshida, Masaki; Okano, Tomomichi

    2014-01-01

    We investigated the effect of the alkyl-chain length of anionic surfactants on the skin using an in vitro model. The evaluated anionic surfactants were sodium alkyl sulfate (AS) and sodium fatty acid methyl ester sulfonate (MES), which had different alkyl-chain lengths (C8-C14). Skin tissue damage and permeability were examined using a reconstructed human epidermal model, LabCyte EPI-MODEL24. Skin tissue damage was examined by measuring cytotoxicity with an MTT assay. Liquid chromatography/tandem mass spectrometry (LC/MS-MS) and liquid chromatography/mass spectrometry (LC/MS) were used to detect surfactants that permeated into the assay medium through an epidermal model. To assess the permeation mechanism and cell damage caused by the surfactants through the epidermis, we evaluated the structural changes of Bovine Serum Albumin (BSA), used as a simple model protein, and the fluidity of 1,2-dipalmitoyl-sn-glycero-3-phosphpcholine (DPPC) liposome, which serves as one of the most abundant phospholipid models of living cell membranes in the epidermis. The effects of the surfactants on the proteins were measured using Circular Dichroism (CD) spectroscopy, while the effects on membrane fluidity were investigated by electron spin resonance (ESR) spectroscopy. ET50 (the 50% median effective time) increased as follows: C10 C12 > C14, for both AS and MES. For both AS and MES, the order parameter, which is the criteria for the microscopic viscosity of lipid bilayers, increased as follows: C10 C12 > C14. It was determined that the difference in skin tissue damage in the LabCyte EPI-MODEL24 with C10 to C14 AS and MES was caused by the difference in permeation and cell membrane fluidity through the lipid bilayer path in the epidermis.

  8. Chain architecture and micellization: A mean-field coarse-grained model for poly(ethylene oxide) alkyl ether surfactants

    Energy Technology Data Exchange (ETDEWEB)

    García Daza, Fabián A.; Mackie, Allan D., E-mail: allan.mackie@urv.cat [Department d’Enginyeria Química, ETSEQ, Universitat Rovira i Virgili, Avinguda dels Països Catalans 26, 43007 Tarragona (Spain); Colville, Alexander J. [Department of Chemical Engineering, Northeastern University, 360 Huntington Avenue, Boston, Massachusetts 02115-5000 (United States)

    2015-03-21

    Microscopic modeling of surfactant systems is expected to be an important tool to describe, understand, and take full advantage of the micellization process for different molecular architectures. Here, we implement a single chain mean field theory to study the relevant equilibrium properties such as the critical micelle concentration (CMC) and aggregation number for three sets of surfactants with different geometries maintaining constant the number of hydrophobic and hydrophilic monomers. The results demonstrate the direct effect of the block organization for the surfactants under study by means of an analysis of the excess energy and entropy which can be accurately determined from the mean-field scheme. Our analysis reveals that the CMC values are sensitive to branching in the hydrophilic head part of the surfactant and can be observed in the entropy-enthalpy balance, while aggregation numbers are also affected by splitting the hydrophobic tail of the surfactant and are manifested by slight changes in the packing entropy.

  9. The ability of single-chain surfactants to emulsify an aqueous-based liquid crystal oscillates with odd-even parity of alkyl-chain length.

    Science.gov (United States)

    Varghese, Nisha; Shetye, Gauri S; Yang, Sijie; Wilkens, Stephan; Smith, Robert P; Luk, Yan-Yeung

    2013-12-15

    The physical properties of many organic molecules often oscillate when the number of carbons in their aliphatic chains changes from odd to even. This odd-even effect for single-chain surfactants in solution is rarely observed. Here, we report the ability of single-chain surfactants to emulsify a class of non-amphiphilic organic salts, disodium cromoglycate (5'DSCG) oscillates as a function of the odd or even number of the aliphatic carbons. This system provides a water-in-oil-in-water emulsion, in which aqueous droplets of 5'DSCG in liquid crystal phases are coated with single-chain surfactants in a bulk carrying aqueous solution. For both surfactants of [Formula: see text] and CH3(CH2)nCOO(-)Na(+), the ability to emulsify 5'DSCG molecules in water is stronger for surfactants with an odd number of sp(3)-hybridized carbon atoms in the aliphatic chains than those with an even number. This observed odd-even effect is consistent with the notion that conventional micelles possess a core of randomly arranged surfactant hydrocarbon tails. However, this water-in-oil-in-water resembles a vesicle system in which the surfactants assemble in a highly ordered structure that separates two aqueous systems. These new self-assembled phases have potential application in the formulation and design of new organic soft materials.

  10. Effect of alkyl length of cationic surfactants on desorption of Cs from contaminated clay

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Bo Hyun; Park, Chan Woo; Yang, Hee Man; Seo, Bum Kyoung; Lee, Kune Woo [Korea Atomic Energy Research Institute, Daejeon (Korea, Republic of); Park, So Jin [Chungnam National University, Daejeon (Korea, Republic of)

    2017-03-15

    In this study, desorption characteristics of Cs from clay according to the hydrophobic alkyl chain length of the cationic surfactant were investigated. Alkyltrimethylammonium bromide was used as a cationic surfactant, and the length of the hydrophobic alkyl chain of the cationic surfactant was varied from –octyl to –cetyl. The adsorbed amount of the cationic surfactant on montmorillonite increased with the length of the hydrophobic alkyl chain, and intercalation of the cationic surfactant into the clay interlayer increased the interlayer distances. The Cs removal efficiency was also enhanced with increasing alkyl chain length, and the cationic surfactant with the cetyl group showed a maximum Cs removal efficiency of 99±2.9%.

  11. Effect of alkyl chain functionalization of ionic liquid surfactants on the complexation and self-assembling behavior of polyampholyte gelatin in aqueous medium.

    Science.gov (United States)

    Singh, Gagandeep; Singh, Gurbir; Kang, Tejwant Singh

    2016-09-21

    The complexation behaviour of an imidazolium based ionic liquid surfactant (ILS) 3-methyl-1-dodecylimidazolium chloride, [C12mim][Cl], and its amide and ester functionalized counterparts 3-(2-(dodecylamino)-2-oxoethyl)-1-methyl-1H-imidazol-3-ium chloride, [C12Amim][Cl], and 3-methyl-1-dodecyloxycarbonylmethylimidazolium chloride, [C12Emim][Cl], with a model protein gelatin (G) in aqueous solution has been investigated. Complexation of G with ILSs at the air-solution interface has been monitored by tensiometry, whereas complexation and ILS mediated self-assembly of G-ILS complexes in the bulk have been followed by dynamic light scattering (DLS), zeta-potential measurements, conductivity, and fluorescence techniques. The morphology of different self-assembled architectures has been monitored by scanning electron microscopy (SEM). Different transitions observed from various techniques in different concentration regimes of ILSs have been assigned to the varying extent of complexation and ILS mediated self-assembly of G-ILS complexes. The functionalization of the alkyl chain of the ILS [C12mim][Cl] with an amide ([C12Amim][Cl]) or ester ([C12Emim][Cl]) moiety owing to their additional hydrogen bonding (H-bonding) ability along with rigidity ([C12Amim][Cl]) or flexibility ([C12Emim][Cl]) near the imidazolium head group has been found to exert great influence on their complexation with G. This influence is fashioned as self-assembled structures of G-ILS complexes into discrete large hexagonal sheet-like or near spherical architectures, depending on the concentration and type of functionality of the alkyl chain of ILSs. The thermodynamic forces behind the complexation and self-assembly processes have been monitored by isothermal titration calorimetry (ITC) measurements and are discussed in detail. As both the nature of the ILS and protein (charge and structure) could affect their interactional behavior, the present results are expected to be very useful in deeply

  12. Polyfluorinated alkyl phosphate ester surfactants - current knowledge and knowledge gaps

    DEFF Research Database (Denmark)

    Taxvig, Camilla; Rosenmai, Anna Kjerstine; Vinggaard, Anne Marie

    2014-01-01

    information on fluorochemicals. Polyfluorinated alkyl phosphate ester surfactants (PAPs) belong to the group of polyfluorinated alkyl surfactants. They have been detected in indoor dust and are widely used in food-contact materials, from which they have the ability to migrate into food. Toxicological data...

  13. Interaction between DNA and Trimethyl-Ammonium Bromides with Different Alkyl Chain Lengths

    Directory of Open Access Journals (Sweden)

    Chao Cheng

    2014-01-01

    Full Text Available The interaction between λ—DNA and cationic surfactants with varying alkyl chain lengths was investigated. By dynamic light scattering method, the trimethyl-ammonium bromides-DNA complex formation was shown to be dependent on the length of the surfactant’s alkyl chain. For surfactants with sufficient long alkyl chain (CTAB, TTAB, DTAB, the compacted particles exist with a size of ~60–110 nm at low surfactant concentrations. In contrast, high concentration of surfactants leads to aggregates with increased sizes. Atomic force microscope scanning also supports the above observation. Zeta potential measurements show that the potential of the particles decreases with the increase of surfactant concentration (CTAB, TTAB, DTAB, which contributes much to the coagulation of the particles. For OTAB, the surfactant with the shortest chain in this study, it cannot fully neutralize the charges of DNA molecules; consequently, the complex is looser than other surfactant-DNA structures.

  14. Branched alkyl alcohol propoxylated sulfate surfactants for improved oil recovery

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Y.; Iglauer, S.; Shuler, P.; Tang, Y. [California Institute of Technology, Covina, CA (US). Power, Environmental and Energy Research (PEER) Center; Goddard, W.A. III [California Institute of Technology, Pasadena, CA (United States). Materials and Process Simulation Center

    2010-05-15

    This investigation considers branched alkyl alcohol propoxylated sulfate surfactants as candidates for chemical enhanced oil recovery (EOR) applications. Results show that these anionic surfactants may be preferred candidates for EOR as they can be effective at creating low interfacial tension (IFT) at dilute concentrations, without requiring an alkaline agent or cosurfactant. In addition, some of the formulations exhibit a low IFT at high salinity, and hence may be suitable for use in more saline reservoirs. Adsorption tests onto kaolinite clay indicate that the loss of these surfactants can be comparable to or greater than other types of anionic surfactants. Surfactant performance was evaluated in oil recovery core flood tests. Selected formulations recovered 35-50% waterflood residual oil even with dilute 0.2 wt% surfactant concentrations from Berea sandstone cores. (orig.)

  15. Micellization of alkyl-propoxy-ethoxylate surfactants in water-polar organic solvent mixtures.

    Science.gov (United States)

    Sarkar, Biswajit; Lam, Stephanie; Alexandridis, Paschalis

    2010-07-06

    The effects of cosolvents (glycerol, ethanol, and isopropanol) on the self-assembly of novel alkyl-propoxy-ethoxylate surfactants in aqueous solutions have been investigated with a focus on the (i) quantification of solvent effects on the critical micelle concentration (cmc), (ii) free-energy contributions to micellization, (iii) local environment in the micellar solution, and (iv) structure of the micelles. The introduction of the polar organic solvents considered in this work into water decreases cohesive forces in the solvent mixture, resulting in an increase in the solubility of the surfactant molecules. As a result, micelle formation becomes less favorable and the cmc increases. The contribution of the cosolvent to the free energy of micellization is positive, and the data for different mixed solvents collapse onto a single straight line when plotted versus a function of the solubility parameters of the surfactant alkyl chains and the mixed solvents. The behavior of the poly(propylene oxide) part of the alkyl-propoxy-ethoxylate surfactants is hydrophilic, albeit less so in the ethanol-water mixed solvent than in plain water. Pyrene fluorescence emission I(1)/I(3) data suggest that the microenvironment in micellar solutions is affected mainly by the cosolvent concentration, not the surfactant degree of ethoxylation. Small-angle X-ray scattering data for both water and ethanol-water surfactant solutions are consistent with oblate ellipsoid micelles and reveal that the introduction of 20% ethanol decreases the micelle long axis by 10-15%.

  16. Formulation of solid lipid nanoparticles (SLN): the value of different alkyl polyglucoside surfactants.

    Science.gov (United States)

    Keck, Cornelia M; Kovačević, Andjelka; Müller, Rainer H; Savić, Snežana; Vuleta, Gordana; Milić, Jela

    2014-10-20

    Alkyl polyglycosides (APGs) represent a group of nonionic tensides with excellent skin compatibility. Thus they seem to be excellent stabilizers for lipid nanoparticles for dermal application. To investigate this, different APGs were selected to evaluate their influence on the formation and characteristics of solid lipid nanoparticles (SLN). Contact angle analysis of the aqueous solutions/dispersions of the APGs on cetyl palmitate films revealed good wettability for all APG surfactants. Cetyl palmitate based SLN were prepared by hot high pressure homogenization and subjected to particle size, charge and inner structure analysis. 1% of each APG was sufficient to obtain SLN with a mean size between 150 nm and 175 nm and a narrow size distribution. The zeta potential in water was ∼ -50 mV; the values in the original medium were distinctly lower, but still sufficient high to provide good physical stability. Physical stability at different temperatures (5°C, 25°C and 40°C) was confirmed by a constant particle size over an observation period of 90 days in all dispersions. In comparison to SLN stabilized with classical surfactants, e.g., Polysorbate, APG stabilized SLN possess a smaller size, improved physical stability and contain less surfactant. Therefore, the use of APGs for the stabilization of lipid nanoparticles is superior in comparison to classical stabilizers. Further, the results indicate that the length of the alkyl chain of the APG influences the diminution efficacy, the final particle size and the crystallinity of the particles. APGs with short alkyl chain led to a faster reduction in size during high pressure homogenization, to a smaller particle size of the SLN and to a lower recrystallization index, i.e., to a lower crystallinity of the SLN. The crystallinity of the SLN increased with an increase in the alkyl chain length of APGs. Therefore, by using the tested APGs differing in the alkyl chain length, not only small sized and physically stable but

  17. How Chain Length and Charge Affect Surfactant Denaturation of Acyl Coenzyme A Binding Protein (ACBP)

    DEFF Research Database (Denmark)

    Andersen, Kell Kleiner; Otzen, Daniel

    2009-01-01

    Using intrinsic tryptophan fluorescence, equilibria and kinetics of unfolding of acyl coenzyme A binding protein (ACBP) have been investigated in sodium alkyl sulfate surfactants of different chain length (8-16 carbon atoms) and with different proportions of the nonionic surfactant dodecyl...... maltoside (DDM). The aim has been to determine how surfactant chain length and micellar charge affect the denaturation mechanism. ACBP denatures in two steps irrespective of surfactant chain length, but with increasing chain length, the potency of the denaturant rises more rapidly than the critical micelle...... constants increases linearly with denaturant concentration below the cmc but declines at higher concentrations. Both shortening chain length and decreasing micellar charge reduce the overall kinetics of unfolding and makes the dependence of unfolding rate constants on surfactant concentration more complex...

  18. Alkyl propoxy ethoxylate "graded" surfactants: micelle formation and structure in aqueous solutions.

    Science.gov (United States)

    Sarkar, Biswajit; Alexandridis, Paschalis

    2010-04-08

    The self-assembly of alkyl propoxy ethoxylate surfactants in aqueous solutions has been investigated with a focus on the (i) thermodynamics of micellization (critical micellization concentration; free energy, enthalpy, and entropy of micellization) and (ii) structure of the micelles (overall shape and size; local environment in the micelle core and corona) as affected by the surfactant composition (variation of degree of ethoxylation). The various results are compared to those for alkyl ethoxylate and poly(ethylene oxide)-b-poly(propylene oxide) amphiphiles with the aim to elucidate the role of the middle, propoxy, block in the novel alkyl propoxy ethoxylate surfactants which exhibit a "graded" hydrophobic-hydrophilic character.

  19. Alkyl-imidazolium glycosides: non-ionic-cationic hybrid surfactants from renewable resources.

    Science.gov (United States)

    Salman, Abbas Abdulameer; Tabandeh, Mojtaba; Heidelberg, Thorsten; Hussen, Rusnah Syahila Duali; Ali, Hapipah Mohd

    2015-08-14

    A series of surfactants combining carbohydrate and imidazolium head groups were prepared and investigated on their assembly behavior. The presence of the imidazolium group dominated the interactions of the surfactants, leading to high CMCs and large molecular surface areas, reflected in curved rather than lamellar surfactant assemblies. The carbohydrate, on the other hand, stabilized molecular assemblies slightly and reduced the surface tension of surfactant solutions considerably. A comparative emulsion study discourages the use of pure alkyl imidazolium glycosides owing to reduced assembly stabilities compared with APGs. However, the surfactants are believed to have potential as component in carbohydrate based surfactant mixtures.

  20. Alkyl polyglycoside/1-naphthol formulations. A case study of surfactant enhanced oil recovery

    Energy Technology Data Exchange (ETDEWEB)

    Iglauer, Stefan; Wu, Yongfu; Shuler, Patrick; Tang, Yongchun [California Institute of Technology, Covina, CA (United States). Div. of Chemistry and Chemical Engineering; Goddard, William A. III [California Institute of Technology, Pasadena, CA (United States). Div. of Chemistry and Chemical Engineering

    2011-03-15

    We present a case study of surfactant enhanced oil recovery using Alkyl polyglucoside/1-naphthol formulations. Alkyl polyglucosides are a green, non-toxic and renewable surfactant class synthesized out of agricultural raw materials. We measured interfacial tensions versus n-octane and viscosities of these formulations and conducted one coreflood enhanced oil recovery (EOR) experiment where we recovered 82.6 % of initial oil in place demonstrating that these formulations are efficient EOR agents. (orig.)

  1. New cationic vesicles prepared with double chain surfactants from arginine: Role of the hydrophobic group on the antimicrobial activity and cytotoxicity.

    Science.gov (United States)

    Pinazo, A; Petrizelli, V; Bustelo, M; Pons, R; Vinardell, M P; Mitjans, M; Manresa, A; Perez, L

    2016-05-01

    Cationic double chain surfactants have attracted much interest because they can give rise to cationic vesicles that can be used in biomedical applications. Using a simple and economical synthetic approach, we have synthesized four double-chain surfactants with different alkyl chain lengths (LANHCx). The critical aggregation concentration of the double chain surfactants is at least one order of magnitude lower than the CMC of their corresponding single-chain LAM and the solutions prepared with the LANHCx contain stable cationic vesicles. Encouragingly, these new arginine derivatives show very low haemolytic activity and weaker cytotoxic effects than conventional dialkyl dimethyl ammonium surfactants. In addition, the surfactant with the shortest alkyl chain exhibits good antimicrobial activity against Gram-positive bacteria. The results show that a rational design applied to cationic double chain surfactants might serve as a promising strategy for the development of safe cationic vesicular systems.

  2. Preparation of quinolinium salts differing in the length of the alkyl side chain.

    Science.gov (United States)

    Marek, Jan; Buchta, Vladimir; Soukup, Ondrej; Stodulka, Petr; Cabal, Jiri; Ghosh, Kallol K; Musilek, Kamil; Kuca, Kamil

    2012-05-25

    Quaternary quinolinium salts differing in alkyl chain length are members of a widespread group of cationic surfactants. These compounds have numerous applications in various branches of industry and research. In this work, the preparation of quinoline-derived cationic surface active agents differing in the length of the side alkyl chains (from C₈ to C₂₀) is described. An HPLC method was successfully developed for distinction of all members of the series of prepared long-chain quinolinium derivatives. In conclusion, some possibilities of intended tests or usage have been summarized. In vitro testing using a microdilution broth method showed good activity of a substance with a C12 chain length against Gram-positive cocci and Candida species.

  3. Alkyl chains acting as entropy reservoir in liquid crystalline materials.

    Science.gov (United States)

    Sorai, Michio; Saito, Kazuya

    2003-01-01

    The roles played by the conformational disordering of alkyl chains in determining the aggregation states of matter are reviewed for liquid crystalline materials from a thermodynamic perspective. Entropy, which is one of the most macroscopic concepts but which has a clear microscopic meaning, provides crucial microscopic information for complex systems for which a microscopic description is hard to establish. Starting from structural implication by absolute (third-law) entropy for crystalline solids, the existence of successive phase transitions caused by the successive conformational melting of alkyl chains in discotic mesogens is explained. An experimental basis is given for the "quasi-binary picture" of thermotropic liquid crystals, i.e., the highly disordered alkyl chains behave like a second component (solvent). A novel entropy transfer between the "components" of a molecule and the resulting "alkyl chains as entropy reservoir" mechanism are explained for cubic mesogens.

  4. Switchable Surfactants

    National Research Council Canada - National Science Library

    Yingxin Liu; Philip G. Jessop; Michael Cunningham; Charles A. Eckert; Charles L. Liotta

    2006-01-01

    .... We report that long-chain alkyl amidine compounds can be reversibly transformed into charged surfactants by exposure to an atmosphere of carbon dioxide, thereby stabilizing water/alkane emulsions...

  5. Interplay between alkyl chain asymmetry and cholesterol addition in the rigid ion pair amphiphile bilayer systems

    Science.gov (United States)

    Huang, Fong-yin; Chiu, Chi-cheng

    2017-01-01

    Ion pair amphiphile (IPA), a molecular complex composed of a pair of cationic and anionic surfactants, has been proposed as a novel phospholipid substitute. Controlling the physical stability of IPA vesicles is important for its application developments such as cosmetic and drug deliveries. To investigate the effects of IPA alkyl chain combinations and the cholesterol additive on the structural and mechanical properties of IPA vesicular bilayers, we conducted a series of molecular dynamics studies on the hexadecyltrimethylammonium-dodecylsulfate (HTMA-DS) and dodecyltrimethylammonium-hexadecylsulfate (DTMA-HS) IPA bilayers with cholesterol. We found that both IPA bilayers are in the gel phase at 298 K, consistent with experimental observations. Compared with the HTMA-DS system, the DTMA-HS bilayer has more disordered alkyl chains in the hydrophobic region. When adding cholesterol, it induces alkyl chain ordering around its rigid sterol ring. Yet, cholesterol increases the molecular areas for all species and disturbs the molecular packing near the hydrophilic region and the bilayer core. Cholesterol also promotes the alkyl chain mismatch between the IPA moieties, especially for the DTMA-HS bilayer. The combined effects lead to non-monotonically enhancement of the membrane mechanical moduli for both IPA-cholesterol systems. Furthermore, cholesterol can form H-bonds with the alkylsulfate and thus enhance the contribution of alkylsulfate to the overall mechanical moduli. Combined results provide valuable molecular insights into the roles of each IPA component and the cholesterol on modulating the IPA bilayer properties.

  6. Interactions of short chain phenylalkanoic acids within ionic surfactant micelles in aqueous media

    Directory of Open Access Journals (Sweden)

    Naeem Kashif

    2012-01-01

    Full Text Available % SDS KR nema Solubilization and interactions of phenylalkanoic acids induced by cationic surfactant, cetyltrimethylammonium bromide (CTAB and an anionic surfactant, sodium dodecyl sulfate (SDS was investigated spectrophotometrically at 25.0°C. The UV spectra of the additives (acids were measured with and without surfactant above and below critical micelle concentration (cmc of the surfactant. The presence of alkyl chain in phenylalkanoic acids is responsible for hydrophobic interaction resulting in shift of the spectra towards longer wavelength (red shift. The value of partition coefficient (Kx between the bulk water and surfactant micelles and in turn standard free energy change of solubilization (ΔGpº were also estimated by measuring the differential absorbance (ΔA of the additives in micellar solutions.

  7. Middle-phase microemulsions of green surfactant alkyl polyglucosides

    Institute of Scientific and Technical Information of China (English)

    CHAI; Jinling; (柴金岭); LI; Ganzuo; (李干佐); ZHANG; Gaoyong; (张高勇); LOU; Anjing; ZHANG; Jian; (张剑); ZHANG; Yue; (张越)

    2003-01-01

    The microemulsion behavior in the quaternary system alkyl polyglucoside (C8G1.46 , C10G1.54)/1-butanol/cyclohexane/water has been studied at 40℃ with the alcohol concentration scanning and the fishlike phase diagram methods. Increasing δat a constant γ causes a phase inversion from an oil-in-water microemulsion in contact with excess oil (Winsor I or 2 ) to a water-in-oil microemulsion in contact with excess water (Winsor Ⅲ or ) via a middle-phase microemulsionin contact with excess oil and water (Winsor Ⅲ or 3). By using the simple mass balance equation and the HLB plane equation, the mass fraction of 1-butanol in the interfacial layer, S s2, the monomeric solubilities of APG and 1-butanol, S1 and S2, in the oil phase, and the mass fractions of APG and 1-butanol in the interfacial layer (C1 and C2 ) have been calculated, respectively. The effects of different alcohols, aqueous media and oils on the phase behavior and the composition of the interfacial layer are also investigated. It is found that the alcohols with longer hydrocarbon chain, oil molecules with smaller molecular volume and the addition of inorganic salt can increase the solubilization of the microemulsions .

  8. Bending of the Flexible Spacer Chain of Gemini Surfactant Induced by Hydrophobic Interaction

    Institute of Scientific and Technical Information of China (English)

    YOU,Yi; JIANG,Rong; LING,Tingting; ZHAO,Jianxi

    2009-01-01

    In order to understand the special role of the flexible alkylene spacer of gemini surfactant in the self-assembly,three gemini surfactants,alkylene-α,ω-bis(didodecylmethylammonium bromide)that is designated as 2C12-s-2C12·2Br (s=3,6,8),were synthesized.When the spread films of 2C12-s-2C12·2Br on the surface of water were con-structed,they form the dense layer of the alkyl tails owing to four dodecyl chains per molecule.This induced the bending of the spacer chain toward the air-side at the s smaller than that of C12-s-C12·2Br adsorbed on the air/water interface owing to the enhanced hydrophobic interaction between the alkyl tails and the spacer chain, where C12-s-C12·2Br has only two alkyl tails per molecule. Conclusively.,the enhanced hydrophobic interaction between the alkyl tails and the spacer chain can effectively induce the bending of the latter toward the air-side.

  9. Synthesis, surface properties, and biocompatibility of 1,2,3-triazole-containing alkyl β-D-xylopyranoside surfactants.

    Science.gov (United States)

    Oldham, E Davis; Seelam, Srivenu; Lema, Carolina; Aguilera, Renato J; Fiegel, Jennifer; Rankin, Stephen E; Knutson, Barbara L; Lehmler, Hans-Joachim

    2013-09-20

    We are interested in the development of surfactants derived from hemicellulosic biomass, as they are potential components in pharmaceuticals, personal care products, and other detergents. Such surfactants should exhibit low toxicity in mammalian cells. In this study we synthesized a series of alkyl or fluoroalkyl β-xylopyranosides from azides and an alkyne using the copper-catalyzed azide-alkyne (CuAAC) 'click' reaction in 4 steps from xylose. The purified products were evaluated for both their surfactant properties, and for their biocompatibility. Unlike other carbohydrate-based surfactants, liquid-crystalline behavior was not observed by differential scanning calorimetry. The triazole-containing β-xylopyranosides with short (6 carbons) and long (>12 carbons) chains exhibited no toxicity at concentrations ranging from 1 to 1000 μM. Triazole-containing β-xylopyranosides with 8, 10, or 12 carbons caused toxicity via apoptosis, with CC50 values ranging from 26-890 μM. The two longest chain compounds did form stable monolayers at the air-water interface over a range of temperatures, although a brief transition to an the unstable monolayer was observed.

  10. Biotransformation of linear alkylbenzene sulfonate (LAS) by Phanerochaete chrysosporium: oxidation of alkyl side-chain.

    Science.gov (United States)

    Yadav, J S; Lawrence, D L; Nuck, B A; Federle, T W; Reddy, C A

    2001-01-01

    The white rot fungus Phanerochaete chrysosporium, which generally mineralizes substituted aromatics to CO2, transformed linear alkylbenzene sulfonate (LAS) surfactants mainly at their alkyl side chain. Degradation of LAS was evidenced by a zone of clearing on LAS-containing agar plates and colorimetric analysis of liquid cultures. Disappearance of LAS was virtually complete within 10 days in low nitrogen (2.4 mM N), high nitrogen (24 mM N) and malt extract (ME) liquid media. After 5 days of incubation in ME medium, transformation of LAS was complete at concentrations < or = 4 mg l(-1), but decreased at higher concentrations. The LAS degradation was not dependent on lignin peroxidases (LiPs) and manganese-dependent peroxidases (MnPs). Mineralization of 14C-ring-LAS to 14CO2 by P. chrysosporium was < 1% regardless of the culture conditions used. Thin layer chromatography and mass spectral analyses indicated that P. chrysosporium transformed LAS to sulfophenyl carboxylates (SPCs) through oxidative shortening of the alkyl side-chains. While LAS disappearance in the cultures was not dependent on LiPs and MnPs, transformation of the parent LAS moieties to SPCs was more extensive in low N medium that favors expression of these enzymes. The SPCs produced in LN cultures were shorter in chain- length than those produced in ME cultures. Also there was a notable shift in the relative abundance of odd and even chain length metabolites compared to the starting LAS particularly in the low N cultures suggesting the possible involvement of processes other than or in addition to beta-oxidation in the chain-shortening process.

  11. Tools to discover anionic and nonionic polyfluorinated alkyl surfactants by liquid chromatography electrospray ionisation mass spectrometry

    DEFF Research Database (Denmark)

    Trier, Xenia; Granby, Kit; Christensen, Jan H.

    2011-01-01

    A tiered approach is proposed for the discovery of unknown anionic and nonionic polyfluorinated alkyl surfactants (PFASs) by reversed phase ultra high performance liquid chromatography (UHPLC) – negative electrospray ionisation – quadrupole time of flight mass spectrometry (UHPLC......–ESI−–QTOF–MS). The chromatographic separation, ionisation and detection of PFASs mixtures, was achieved at high pH (pH=9.7) with NH4OH as additive. To distinguish PFASs from other chemicals we used the characteristic negative mass defects of PFASs, their specific losses of 20Da (HF) and the presence of series of chromatographic...

  12. Synthesis, surface-active properties, and antimicrobial activities of new double-chain gemini surfactants.

    Science.gov (United States)

    Murguía, Marcelo C; Vaillard, Victoria A; Sánchez, Victoria G; Conza, José Di; Grau, Ricardo J

    2008-01-01

    A novel series of neutral and cationic dimeric surfactants were prepared involving ketalization reaction, Williamson etherification, and regioselective oxirane ring opening with primary and tertiary alkyl amines. The critical micelle concentration (CMC), effectiveness of surface tension reduction (gamma(CMC)), surface excess concentration (Gamma), and area per molecule at the interface (A) were determined and values indicate that the cationic series is characterized by good surface-active and self-aggregation properties. For the first time, we reported the antimicrobial activities against representative bacteria and fungi for dimeric compounds. The antimicrobial activity was found to be dependent on the target microorganism (Gram-positive bacteria > fungi > Gram-negative bacteria), as well as both the neutral or ionic nature (cationic > neutral) and alkyl chain length (di-C(12) > di-C(18) > di-C(8)) of the compounds. The cationic di-C(12) derivative was found to have equipotent activity to that of benzalkonium chloride (BAC) used as standard.

  13. Effect of foamability index of short chain alkyl amines on flotation of quartz

    Directory of Open Access Journals (Sweden)

    Szczerkowska Sabina

    2016-01-01

    Full Text Available Amines can be used for flotation of various minerals, especially quartz. The flotation efficiency of quartz depends on the amine type and dose. It was proved that the shorter alkyl amine, higher amine concentration has to be used to recover quartz at the same level. In flotation amines play a role of both collectors and frothers. The ability of a amine to collect particles can be expressed in the form of contact angle, while the foaming properties by different parameters including dynamic foamability index (DFI and critical coalescence concentration (CCC. Determination of DFI and CCC requires advanced techniques and methods. Therefore, in this paper a rapid and facile method for determination of foaming properties of amines and also other surfactants was used. It was based on measuring the initial foam and froth heights in a conventional flotation machine at different concentrations of surfactants. The foam height-concentration curve was described by utilizing an empirical equation which was based on one-adjustable parameter called the foamability index (FI. In this work the foamability index was determined for butylamine (ButNH2, hexylamine (HexNH2 and octylamine (OctNH2 as examples of short chain alkyl amines. The determined foamability indices were 92, 12 and 4 mg/dm3 for ButNH2, HexNH2 and OctNH2, respectively. It was shown that when the flotation results of quartz were presented in the form of recovery versus normalized amine concentration in relation to the foamability index (c/FI, all the experimental data points converged to one curve. It indicates that amines act similarly but at different concentrations expressed as FI. The foamability index seems to be a useful parameter for characterizing any flotation frother.

  14. Sources and proxy potential of long chain alkyl diols in lacustrine environments.

    NARCIS (Netherlands)

    Rampen, Sebastiaan W.; Datema, Mariska; Rodrigo-Gámiz, M.; Schouten, Stefan; Reichart, Gert-Jan; Sinninghe Damste, Jaap S.

    2014-01-01

    Long chain 1,13- and 1,15-alkyl diols form the base of a number of recently proposed proxies used for climate reconstruction. However, the sources of these lipids and environmental controls on their distribution are still poorly constrained. We have analyzed the long chain alkyl diol (LCD) compositi

  15. Sources and proxy potential of long chain alkyl diols in lacustrine environments

    NARCIS (Netherlands)

    Rampen, S.; Datema, M.; Rodrigo-Gámiz, M.; Schouten, S.; Reichart, G.-J.; Sinninghe Damsté, J.S.

    2014-01-01

    Long chain 1,13- and 1,15-alkyl diols form the base of a number of recently proposed proxies used for climate reconstruction. However, the sources of these lipids and environmental controls on their distribution are still poorly constrained. We have analyzed the long chain alkyl diol (LCD) compositi

  16. Synthesis of a Novel Surfactant with Two Alkyl Tail-Chains (DDOBA) and Fabrication of Hydrophobic Gold Nanoparticles with High Monodispersity%新型双链表面活性剂DDOBA的合成与高单分散性憎水纳米金的制备

    Institute of Scientific and Technical Information of China (English)

    韩莹; 朱露; 沈明; 李恒恒

    2013-01-01

    3,4-Didodecyloxybenzylamine (DDOBA), a novel surfactant with two alkyl tail-chains, was designed and synthesized. DDOBA-capped hydrophobic gold nanoparticles were successful y fabricated using formic acid as a reducing agent in a DDOBA/n-butanol/n-heptane/formic acid/HAuCl4·4H2O water/oil (W/O) microemulsion system under microwave irradiation. DDOBA-stabilized gold nanoparticles were characterized by ultraviolet-visible (UV-Vis) spectroscopy, transmission electron microscopy (TEM), high resolution transmission electron microscopy (HR-TEM), and X-ray diffraction (XRD). The experimental results showed that DDOBA not only participated in the formation of a stable W/O microemulsion system, but also became a good protecting agent for gold nanoparticles. Within an appropriate concentration range of components in the W/O microemulsion system, hydrophobic gold nanoparticles with high monodispersity can be obtained using this experimental method and automatical y form large areas of ordered monolayer built with DDOBA-capped gold nanoparticles at the air/water interface.%  自行设计合成了新颖的苄胺型双链表面活性剂3,4-双十二烷氧基苄胺(DDOBA)。利用DDOBA/正丁醇/正庚烷/甲酸/HAuCl4·4H2O自发形成的水/油(W/O)型微乳液作为微反应器,通过微波辐射下的甲酸还原法成功制备了DDOBA保护的憎水性金纳米粒子,并通过紫外-可见(UV-Vis)光谱、透射电镜(TEM)、高分辨透射电镜(HR-TEM)和X射线衍射(XRD)等方法进行了表征和分析。结果显示, DDOBA既可参与形成稳定的W/O型(油包水型)微乳液,又可作为金纳米粒子的良好保护剂。在合适的微乳液体系组成范围内,用本实验方法可以获得高单分散性的憎水性金纳米粒子,并能在空气/水界面上自动形成大面积短程有序的纳米金二维自组装膜。

  17. Soluble Polyimides Bearing Long-Chain Alkyl Groups on Their Side Chain via Polymer Reaction

    Directory of Open Access Journals (Sweden)

    Yusuke Tsuda

    2012-01-01

    Full Text Available Novel soluble polyimides having long-chain alkyl groups on their side chain were synthesized via polymer reaction with the polyimides having phenolic OH groups and 3,4,5-tris(dodecyloxybenzoic acid (12GA using N,N′-dicyclohexylcarbodiimide (DCC as a dehydration reagent. The polyimides having phenolic OH groups were synthesized from the tetracarboxylic dianhydrides such as 5-(2,5-dioxotetrahydrofuryl-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride (cyclohexene-DA, 4,4′-hexafluoroisopropylidendi(phthalic anhydride (6FDA, and 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride (DSDA and aromatic diamines such as 4,4′-diamino-3,3′-dihydroxybiphenyl (HAB. The polymer reactions were carried out in NMP and the progresses of polymer reactions were quantitatively monitored by 1H NMR measurements (conversion; 12.2–98.7%. The obtained polyimides bearing long-chain alkyl groups have enough molecular weights, good film-forming ability, good solubility for various organic solvents, and enough thermal stability. The water contact angles of the polyimide films were investigated, and it is noted that the introduction of long-chain alkyl groups increases the hydrophobicity of polyimide surface. These polyimides are expected to be applicable as the functional materials for microelectronics such as the alignment layers of LCDs.

  18. Structure, interfacial properties, and dynamics of the sodium alkyl sulfate type surfactant monolayer at the water/trichloroethylene interface: a molecular dynamics simulation study.

    Science.gov (United States)

    Shi, Wen-Xiong; Guo, Hong-Xia

    2010-05-20

    In this work, we perform a series of molecular dynamics (MD) simulations on the category of sodium alkyl sulfate (SDS-type) surfactant monolayers at the water/trichloroethylene (TCE) interface. Three separate tail-length SDS-type molecules are used. We investigate the conformation of surfactant chain (i.e., packing, orientation, and order), interfacial properties (i.e., interfacial thickness, interfacial tension, area compressibility, and bending modulus), their dependence on the chain length, and the average area per surfactant chain. We also examine the behavior of the surfactant monolayer in the metastable regime of negative surface tension with reference to collapse. The simulation has clearly shown that the very dilute monolayer is well described as a two-dimensional gas. With the increase of interfacial surfactant coverage, the monolayer is in the liquid-expanded (LE) phase. The surfactant tails at the interface become straighter, more ordered, and thicker at higher surfactant coverage. At the same time, interfacial tension of long-tail systems is always lower than that of short-tail systems. In the LE phase, the area compressibility modulus and the bending modulus increase with an increase in tail length. With a further decrease in molecular areas, the monolayer with large negative surface tension becomes unstable. Our simulations show that buckling of the monolayers is of dynamic nature as a response to mechanical instability. The further transformation pathway from buckling to bud can be controlled by the bending modulus, which depends crucially on the tail length and interfacial surfactant coverage. At a given area per molecule, the short tail chain makes the monolayer softer, and the budding process becomes more probable. For the supersaturated softer SDS monolayer, the collapse transition is initiated by the buckling of monolayers, followed primarily by budding and detachment of the nanoscale swollen micelle from the monolayer. Despite a number of

  19. Effects of alkyl side chains on properties of aliphatic amino acids probed using quantum chemical calculations.

    Science.gov (United States)

    Ganesan, Aravindhan; Wang, Feng; Brunger, Michael; Prince, Kevin

    2011-09-01

    Effects of alkyl side chains (R-) on the electronic structural properties of aliphatic amino acids are investigated using quantum mechanical approaches. The carbon (C 1s) binding energy spectra of the aliphatic amino acids are derived from the C 1s spectrum of glycine (the parent spectrum) by the addition of spectral peaks, depending on the alkyl side chains, appearing in the lower energy region IP aliphatic amino acids owing to perturbations depending on the size and structure of the alkyl chains. The pattern of the N 1s and O 1s spectra in glycine is retained in the spectra of the other amino acids with small shifts to lower energy, again depending on the alkyl side chain. The Hirshfeld charge analyses confirm the observations. The alkyl effects on the valence binding energy spectra of the amino acids are concentrated in the middle valence energy region of 12-16 eV, and hence this energy region of 12-16 eV is considered as the `fingerprint' of the alkyl side chains. Selected valence orbitals, either inside or outside of the alkyl fingerprint region, are presented using both density distributions and orbital momentum distributions, in order to understand the chemical bonding of the amino acids. It is also observed that the HOMO-LUMO energy gaps of the aliphatic amino acids are reduced with the growth of the alkyl side chain.

  20. Soluble Polyimides Bearing Long-Chain Alkyl Groups on Their Side Chain via Polymer Reaction

    OpenAIRE

    2012-01-01

    Novel soluble polyimides having long-chain alkyl groups on their side chain were synthesized via polymer reaction with the polyimides having phenolic OH groups and 3,4,5-tris(dodecyloxy)benzoic acid (12GA) using N,N′-dicyclohexylcarbodiimide (DCC) as a dehydration reagent. The polyimides having phenolic OH groups were synthesized from the tetracarboxylic dianhydrides such as 5-(2,5-dioxotetrahydrofuryl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride (cyclohexene-DA), 4,4′-hexafluoroisoprop...

  1. EFFECT OF ALKYL CHAIN ASYMMETRY ON THE FUSION AND CRYSTALLIZATION BEHAVIOR OF VESICLES FORMED FROM DI-N-ALKYL PHOSPHATES

    NARCIS (Netherlands)

    STREEFLAND, L; WAGENAAR, A; HOEKSTRA, D; ENGBERTS, JBFN

    1993-01-01

    Fusion of vesicles formed from synthetic, asymmetric (i.e mixed-chain) sodium di-n-alkyl phosphates (1-6) has been studied with a resonance energy transfer assay for lipid mixing and with transmission electron microscopy. Fusion was induced by Ca2+ ions above the Lalpha --> Lbeta phase transition te

  2. Biological and surface-active properties of double-chain cationic amino acid-based surfactants.

    Science.gov (United States)

    Greber, Katarzyna E; Dawgul, Małgorzata; Kamysz, Wojciech; Sawicki, Wiesław; Łukasiak, Jerzy

    2014-08-01

    Cationic amino acid-based surfactants were synthesized via solid phase peptide synthesis and terminal acylation of their α and ε positions with saturated fatty acids. Five new lipopeptides, N-α-acyl-N-ε-acyl lysine analogues, were obtained. Minimum inhibitory concentration and minimum bactericidal (fungicidal) concentration were determined on reference strains of bacteria and fungi to evaluate the antimicrobial activity of the lipopeptides. Toxicity to eukaryotic cells was examined via determination of the haemolytic activities. The surface-active properties of these compounds were evaluated by measuring the surface tension and formation of micelles as a function of concentration in aqueous solution. The cationic surfactants demonstrated diverse antibacterial activities dependent on the length of the fatty acid chain. Gram-negative bacteria and fungi showed a higher resistance than Gram-positive bacterial strains. It was found that the haemolytic activities were also chain length-dependent values. The surface-active properties showed a linear correlation between the alkyl chain length and the critical micelle concentration.

  3. Immobilization of lipases on alkyl silane modified magnetic nanoparticles: effect of alkyl chain length on enzyme activity.

    Directory of Open Access Journals (Sweden)

    Jiqian Wang

    Full Text Available BACKGROUND: Biocatalytic processes often require a full recycling of biocatalysts to optimize economic benefits and minimize waste disposal. Immobilization of biocatalysts onto particulate carriers has been widely explored as an option to meet these requirements. However, surface properties often affect the amount of biocatalysts immobilized, their bioactivity and stability, hampering their wide applications. The aim of this work is to explore how immobilization of lipases onto magnetite nanoparticles affects their biocatalytic performance under carefully controlled surface modification. METHODOLOGY/PRINCIPAL FINDINGS: Magnetite nanoparticles, prepared through a co-precipitation method, were coated with alkyl silanes of different alkyl chain lengths to modulate their surface hydrophobicity. Candida rugosa lipase was then directly immobilized onto the modified nanoparticles through hydrophobic interaction. Enzyme activity was assessed by catalytic hydrolysis of p-nitrophenyl acetate. The activity of immobilized lipases was found to increase with increasing chain length of the alkyl silane. Furthermore, the catalytic activities of lipases immobilized on trimethoxyl octadecyl silane (C18 modified Fe(3O(4 were a factor of 2 or more than the values reported from other surface immobilized systems. After 7 recycles, the activities of the lipases immobilized on C18 modified nanoparticles retained 65%, indicating significant enhancement of stability as well through hydrophobic interaction. Lipase immobilized magnetic nanoparticles facilitated easy separation and recycling with high activity retaining. CONCLUSIONS/SIGNIFICANCE: The activity of immobilized lipases increased with increasing alkyl chain length of the alkyl trimethoxy silanes used in the surface modification of magnetite nanoparticles. Lipase stability was also improved through hydrophobic interaction. Alkyl silane modified magnetite nanoparticles are thus highly attractive carriers for

  4. Alkyl chain length dependence of the field-effect mobility in novel anthracene derivatives.

    Science.gov (United States)

    Back, Jang Yeol; An, Tae Kyu; Cheon, Ye Rim; Cha, Hyojung; Jang, Jaeyoung; Kim, Yebyeol; Baek, Yonghwa; Chung, Dae Sung; Kwon, Soon-Ki; Park, Chan Eon; Kim, Yun-Hi

    2015-01-14

    We report six asymmetric alkylated anthracene-based molecules with different alkyl side chain lengths for use in organic field-effect transistors (OFETs). Alkyl side chains can potentially improve the solubility and processability of anthracene derivatives. The crystallinity and charge mobility of the anthracene derivatives may be improved by optimizing the side chain length. The highest field-effect mobility of the devices prepared here was 0.55 cm(2)/(V s), for 2-(p-pentylphenylethynyl)anthracene (PPEA). The moderate side chain length appeared to be optimal for promoting self-organization among asymmetric anthracene derivatives in OFETs, and was certainly better than the short or long alkyl side chain lengths, as confirmed by X-ray diffraction measurements.

  5. Modification with alkyl chains and the influence on thermal and mechanical properties of aromatic hyperbranched polyesters

    NARCIS (Netherlands)

    Schmaljohann, Dirk; Häußler, Liane; Pötschke, Petra; Voit, Brigitte I.; Loontjens, Ton J.A.

    2000-01-01

    All-aromatic hyperbranched polyesters with hydroxy endgroups were functionalized with aliphatic n-alkyl carboxylic acids. The length of the n-alkyl chain as well as the degree of modification were varied and the resulting, partially amphiphilic polymers were characterized by differential scanning ca

  6. CHARMM36 united atom chain model for lipids and surfactants.

    Science.gov (United States)

    Lee, Sarah; Tran, Alan; Allsopp, Matthew; Lim, Joseph B; Hénin, Jérôme; Klauda, Jeffery B

    2014-01-16

    Molecular simulations of lipids and surfactants require accurate parameters to reproduce and predict experimental properties. Previously, a united atom (UA) chain model was developed for the CHARMM27/27r lipids (Hénin, J., et al. J. Phys. Chem. B. 2008, 112, 7008-7015) but suffers from the flaw that bilayer simulations using the model require an imposed surface area ensemble, which limits its use to pure bilayer systems. A UA-chain model has been developed based on the CHARMM36 (C36) all-atom lipid parameters, termed C36-UA, and agreed well with bulk, lipid membrane, and micelle formation of a surfactant. Molecular dynamics (MD) simulations of alkanes (heptane and pentadecane) were used to test the validity of C36-UA on density, heat of vaporization, and liquid self-diffusion constants. Then, simulations using C36-UA resulted in accurate properties (surface area per lipid, X-ray and neutron form factors, and chain order parameters) of various saturated- and unsaturated-chain bilayers. When mixed with the all-atom cholesterol model and tested with a series of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC)/cholesterol mixtures, the C36-UA model performed well. Simulations of self-assembly of a surfactant (dodecylphosphocholine, DPC) using C36-UA suggest an aggregation number of 53 ± 11 DPC molecules at 0.45 M of DPC, which agrees well with experimental estimates. Therefore, the C36-UA force field offers a useful alternative to the all-atom C36 lipid force field by requiring less computational cost while still maintaining the same level of accuracy, which may prove useful for large systems with proteins.

  7. Hydrocarbon chain conformation in an intercalated surfactant monolayer and bilayer

    Indian Academy of Sciences (India)

    N V Venkataraman; S Vasudevan

    2001-10-01

    Cetyl trimethyl ammonium (CTA) ions have been confined within galleries of layered CdPS3 at two different grafting densities. Low grafting densities are obtained on direct intercalation of CTA ions into CdPS3 to give Cd0.93PS3(CTA)0.14. Intercalation occurs with a lattice expansion of 4.8 Å with the interlamellar surfactant ion lying flat forming a monolayer. Intercalation at higher grafting densities was effected by a two-step ion-exchange process to give Cd0.83PS3(CTA)0.34, with a lattice expansion of 26.5 Å. At higher grafting densities the interlamellar surfactant ions adopt a tilted bilayer structure. 13C NMR and orientation-dependent IR vibrational spectroscopy on single crystals have been used to probe the conformation and orientation of the methylene ‘tail’ of the intercalated surfactant in the two phases. In the monolayer phase, the confined methylene chain adopts an essentially all-trans conformation with most of the trans chain aligned parallel to the gallery walls. On lowering the temperature, molecular plane aligns parallel, so that the methylene chain lies flat, rigid and aligned to the confining surface. In the bilayer phase, most bonds in the methylene chain are in trans conformation. It is possible to identify specific conformational sequences containing a gauche bond, in the interior and termini of the intercalated methylene. These high energy conformers disappear on cooling leaving all fifteen methylene units of the intercalated cetyl trimethyl ammonium ion in trans conformational registry at 40 K.

  8. SYNTHESIS OF POLYFLUORENES BEARING LATERAL PYRENETERMINATED ALKYL CHAINS FOR DISPERSION OF SINGLE-WALLED CARBON NANOTUBES

    Institute of Scientific and Technical Information of China (English)

    Mei-fang Liu; Yu-lan Chen; Bo Zhu; Yang Han; Wei-guo Huang; Chun Du; Zhi-shan Bo

    2012-01-01

    Two kinds of polyfluorenes bearing two lateral pyrene terminated alkyl chains and two alkyl chains per repeating unit were synthesized by Suzuki polycondensation and used to disperse single-walled carbon nanotubes (SWCNT) in organic solvents.Stable polymer-SWCNT complex can be formed via the multivalent π-π stacking interaction of the lateral pyrene functional groups and the polyfluorene backbone with the outer surface of carbon nanotubes; meanwhile the lateral alkyl chains can impart good solubility to the complex.As expected,polyfluorenes bearing lateral pyrene functional groups and octyl chains exhibited much higher carbon nanotube solubility in common organic solvents than the corresponding polyfluorenes beating only octyl chains.Photophysical studies indicated that the formation of polymer-SWCNT complex can effectively quench the fluorescence ofpolyfluorenes.

  9. Effect of varying nonwoven cotton substrate and the properties of the surfactant solution upon the adsorption of aqueous solutions of alkyl-dimethyl-benzyl-ammonium chloride

    Science.gov (United States)

    The adsorption of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC), a cationic surfactant commonly employed as an antimicrobial agent, on greige, alkaline scoured, and bleached nonwoven cotton fabrics was investigated at varying surfactant concentrations and liquor ratios using UV-vis absorption spec...

  10. Structural isomers of polyfluorinated di- and tri-alkylated phosphate ester surfactants present in industrial blends and in microwave popcorn bags

    DEFF Research Database (Denmark)

    Trier, Xenia; Juul Nielsen, Nikoline; Christensen, Jan H.

    2011-01-01

    Introduction In this study, we provide strategies for detecting and quantifying the structural isomers of polyfluorinated di- and tri-alkyl surfactants (PFAS) by mass spectrometry (MS). We specifically investigate polyfluorinated dialkylated phosphate ester surfactants (x:2/y:2 diPAPS, (F(CF2) x CH...

  11. Dependence of cobaltocenium diffusion in ionic liquids on the alkyl chain length of 1-alkyl-3-methylimidazolium cations.

    Science.gov (United States)

    Ueda, Hiroyuki; Nishiyama, Katsuhiko; Yoshimoto, Soichiro

    2016-02-07

    The electrochemical behavior of cobaltocenium (Cc(+)) on a Au(111) electrode was investigated in five 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide ([Cnmim][Tf2N], n = 2, 4, 6, 8, or 10) ionic liquids (ILs) in the temperature range from 293.15 to 343.15 K by cyclic voltammetry and chronoamperometry. The redox couple of Cc(+) exhibited a clear reversible one-electron reaction in all the [Cnmim][Tf2N] ILs. The diffusion coefficients of Cc(+) increased with an increase in the alkyl chain length of [Cnmim](+) and a decrease in the viscosity of the IL upon elevating the temperature. The viscosity of the IL plays an important role in determining the activation energy for the diffusion of Cc(+). The obtained results suggested that the alkyl chain length of [Cnmim](+) affects the strength of the interaction between Cc(+) and the surrounding ion species. The results also clarified that the equation proposed by Sutherland adequately describes the diffusion of Cc(+) in ILs when the effect of the type of IL and the temperature on the product of the Stokes radius of Cc(+) and the Sutherland coefficient is considered.

  12. Micellization Behavior of Long-Chain Substituted Alkylguanidinium Surfactants

    Directory of Open Access Journals (Sweden)

    Roza Bouchal

    2016-02-01

    Full Text Available Surface activity and micelle formation of alkylguanidinium chlorides containing 10, 12, 14 and 16 carbon atoms in the hydrophobic tail were studied by combining conductivity and surface tension measurements with isothermal titration calorimetry. The purity of the resulting surfactants, their temperatures of Cr→LC and LC→I transitions, as well as their propensity of forming birefringent phases, were assessed based on the results of 1H and 13C NMR, differential scanning calorimetry (DSC, and polarizing microscopy studies. Whenever possible, the resulting values of Krafft temperature (TK, critical micelle concentration (CMC, minimum surface tension above the CMC, chloride counter-ion binding to the micelle, and the standard enthalpy of micelle formation per mole of surfactant (ΔmicH° were compared to those characterizing alkyltrimethylammonium chlorides or bromides with the same tail lengths. The value of TK ranged between 292 and 314 K and increased strongly with the increase in the chain length of the hydrophobic tail. Micellization was described as both entropy and enthalpy-driven. Based on the direct calorimetry measurements, the general trends in the CMC with the temperature, hydrophobic tail length, and NaCl addition were found to be similar to those of other types of cationic surfactants. The particularly exothermic character of micellization was ascribed to the hydrogen-binding capacity of the guanidinium head-group.

  13. Micellization Behavior of Long-Chain Substituted Alkylguanidinium Surfactants.

    Science.gov (United States)

    Bouchal, Roza; Hamel, Abdellah; Hesemann, Peter; In, Martin; Prelot, Bénédicte; Zajac, Jerzy

    2016-02-06

    Surface activity and micelle formation of alkylguanidinium chlorides containing 10, 12, 14 and 16 carbon atoms in the hydrophobic tail were studied by combining conductivity and surface tension measurements with isothermal titration calorimetry. The purity of the resulting surfactants, their temperatures of Cr→LC and LC→I transitions, as well as their propensity of forming birefringent phases, were assessed based on the results of ¹H and (13)C NMR, differential scanning calorimetry (DSC), and polarizing microscopy studies. Whenever possible, the resulting values of Krafft temperature (TK), critical micelle concentration (CMC), minimum surface tension above the CMC, chloride counter-ion binding to the micelle, and the standard enthalpy of micelle formation per mole of surfactant (ΔmicH°) were compared to those characterizing alkyltrimethylammonium chlorides or bromides with the same tail lengths. The value of TK ranged between 292 and 314 K and increased strongly with the increase in the chain length of the hydrophobic tail. Micellization was described as both entropy and enthalpy-driven. Based on the direct calorimetry measurements, the general trends in the CMC with the temperature, hydrophobic tail length, and NaCl addition were found to be similar to those of other types of cationic surfactants. The particularly exothermic character of micellization was ascribed to the hydrogen-binding capacity of the guanidinium head-group.

  14. Activated-sludge nitrification in the presence of linear and branched-chain alkyl benzene sulfonates.

    Science.gov (United States)

    Baillod, C R; Boyle, W C

    1968-01-01

    The effects of biodegradable linear alkyl benzene sulfonate and branched-chain alkyl benzene sulfonate detergents on activated-sludge nitrification were investigated by administering a synthetic waste containing up to 23 mg of each detergent per liter to eight bench-scale, batch, activated-sludge units. It was found that both detergents tended to promote complete oxidation of ammonia to nitrate, whereas control units produced approximately equal amounts of nitrite and nitrate. Various hypotheses are offered to explain the phenomenon.

  15. Dependence of micelle size and shape on detergent alkyl chain length and head group.

    Directory of Open Access Journals (Sweden)

    Ryan C Oliver

    Full Text Available Micelle-forming detergents provide an amphipathic environment that can mimic lipid bilayers and are important tools for solubilizing membrane proteins for functional and structural investigations in vitro. However, the formation of a soluble protein-detergent complex (PDC currently relies on empirical screening of detergents, and a stable and functional PDC is often not obtained. To provide a foundation for systematic comparisons between the properties of the detergent micelle and the resulting PDC, a comprehensive set of detergents commonly used for membrane protein studies are systematically investigated. Using small-angle X-ray scattering (SAXS, micelle shapes and sizes are determined for phosphocholines with 10, 12, and 14 alkyl carbons, glucosides with 8, 9, and 10 alkyl carbons, maltosides with 8, 10, and 12 alkyl carbons, and lysophosphatidyl glycerols with 14 and 16 alkyl carbons. The SAXS profiles are well described by two-component ellipsoid models, with an electron rich outer shell corresponding to the detergent head groups and a less electron dense hydrophobic core composed of the alkyl chains. The minor axis of the elliptical micelle core from these models is constrained by the length of the alkyl chain, and increases by 1.2-1.5 Å per carbon addition to the alkyl chain. The major elliptical axis also increases with chain length; however, the ellipticity remains approximately constant for each detergent series. In addition, the aggregation number of these detergents increases by ∼16 monomers per micelle for each alkyl carbon added. The data provide a comprehensive view of the determinants of micelle shape and size and provide a baseline for correlating micelle properties with protein-detergent interactions.

  16. Modification of nano-sized layered double hydroxides by long-chain organic aliphatic surfactants

    OpenAIRE

    RAMASAMY ANBARASAN; SEUNG SOON IM; WANDUC LEE

    2008-01-01

    The inter-layer anion of layered double hydroxides (LDH) with a hydrotalcite (HT)-like structure was ion-exchanged with various organic surfactants, particularly with long chain aliphatic surfactants. After the ion-exchange process, the basal spacing of the LDH was increased and the increase of the basal spacing depended on various factors, such as the intercalation capacity functionality and orientation capability of the surfactant. Of the employed surfactants, stearic acid intercalated LDH ...

  17. Degradable terpolymers with alkyl side chains demonstrate enhanced gene delivery potency and nanoparticle stability.

    Science.gov (United States)

    Eltoukhy, Ahmed A; Chen, Delai; Alabi, Christopher A; Langer, Robert; Anderson, Daniel G

    2013-03-13

    Degradable, cationic poly(β-amino ester)s (PBAEs) with alkyl side chains are developed for non-viral gene delivery. Nanoparticles formed from these PBAE terpolymers exhibit significantly enhanced DNA transfection potency and resistance to aggregation. These hydrophobic PBAE terpolymers, but not PBAEs lacking alkyl side chains, support interaction with PEG-lipid conjugates, facilitating their functionalization with shielding and targeting moieties and accelerating the in vivo translation of these materials. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  18. Effects of alkyl chain positioning on conjugated polymer microstructure and field-effect mobilities

    KAUST Repository

    Schroeder, Bob C.

    2015-07-02

    Solubilizing alkyl chains play a crucial role in the design of semiconducting polymers because they define the materials solubility and processability as well as both the crystallinity and solid-state microstructure. In this paper, we present a scarcely explored design approach by attaching the alkyl side chains on one side (cis-) or on both sides (trans-) of the conjugated backbone. We further investigate the effects of this structural modification on the solid-state properties of the polymers and on the charge-carrier mobilities in organic thin-film transistors. Copyright © Materials Research Society 2015

  19. Optimization of Biodegradability and Toxicity Testing of Degradation Product from Linear Alkyl BenzeneSulfonate (LAS Surfactant as Cleaning Detergent Agent

    Directory of Open Access Journals (Sweden)

    Neera Khairani

    2009-11-01

    Full Text Available Optimization of Biodegradability and Toxicity Testing of Degradation Product from Linear Alkyl BenzeneSulfonate (LAS Surfactant as Cleaning Detergent Agent. Linear Alkyl Benzene Sulfonate (LAS is a surfactantused in laundry detergent as cleaning agent and toxic to aquatic organisms. Results shows, with the LAS concentrationused (20 ppm in medium, adaptation time and Acinetobacter sp. growth has shown better biodegradation ability thanthree other bacteria used Pseudomonas putida, Pseudomonas fluorescence, Bacillaria spp. Thus, Acinetobacter sp isused further for biodegradation process of LAS. Based on its biodegradation half-life using Acinetobacter sp, and withmixed culture (± 52.32% and ± 46.82% respectively could be achieved in 4 (four days, LAS could be categorized as abiodegradable compound. The toxicity assay is based on tetrazolium dye reduction with Rhizobium meliloti as indicatororganism. LAS is more toxic than its intermediate product from biodegradation, with IC50 = 34.35 ppm, and theintermediate product, Ac and Cm, has IC50 = 446.19 ppm and 111.28 ppm respectively. Identification of intermediateproducts using IR and LC-MS analysis shows that the degradation product contains chemicals compounds withfunctional group as follows: benzene, benzoic acid, hydroxyl, and aliphatic carbons with large molecule weight. Untilits half-time degradation time, LAS biodegradation process only occurs at the aliphatic carbon chain, and have not yetreached the stage of aromatic ring opening.

  20. Potential biological sources of long chain alkyl diols in a lacustrine system

    NARCIS (Netherlands)

    Villanueva, Laura; Besseling, Marc; Rodrigo-Gámiz, Marta; Rampen, Sebastiaan W.; Verschuren, Dirk; Sinninghe Damsté, Jaap S.

    2014-01-01

    Long chain alkyl diols (LCDs) have been detected in a range of marine and lacustrine environments, as well as in several algal cultures. However, the identity of the producers, their preferred ecological niche and seasonality are uncertain. We applied a gene-based approach to determine the identity

  1. NMR study of 1,4-dihydropyridine derivatives endowed with long alkyl and functionalized chains

    Energy Technology Data Exchange (ETDEWEB)

    Suarez, Margarita; Salfran, Esperanza; Rodriguez, Hortensia; Coro, Julieta, E-mail: msuarez@fq.uh.c [Universidad de La Habana (Cuba). Facultad de Quimica. Lab. de Sintesis Organica; Molero, Dolores; Saez, Elena [Universidad Complutense, Madrid (Spain). CAI-RMN; Martinez-Alvarez, Roberto; Martin, Nazario [Universidad Complutense, Madrid (Spain). Facultad de Quimica. Dept. de Quimica Organica I

    2011-07-01

    The {sup 1}H , {sup 13}C and {sup 15}N NMR spectroscopic data for 1,4-dihydropyridine endowed with long alkyl and functionalized chain on C-3 and C-5, have been fully assigned by combination of one- and two dimensional experiments (DEPT, HMBC, HMQC, COSY, nOe). (author)

  2. Long chain alkyl and alkenyl phenols from the roots of Ozoroa insignis

    Energy Technology Data Exchange (ETDEWEB)

    Yonghong Liu [Chinese Academy of Sciences, Guangzhou (China). Guangdong Key Lab. of Marine Materia Medica. South China Sea Institute of Oceanology; Abreu, Pedro J.M. [Universidade Nova de Lisboa, Caparica (Portugal). Dept. de Quimica. REQUIMTE

    2006-05-15

    Bioassay-guided fractionation of the ethanolic root extract of Ozoroa insignis, collected in Guinea-Bissau, led to the isolation of a 41-member library of alkyl and alkenylphenols, whose structures were determined by {sup 1}H and {sup 13}C NMR, and GCMS. Determination of double-bond positions in the side chains of alkenylphenols were established by methylthiolation-GCMS. (author)

  3. Determination of monounsaturated alkyl side chain 2-alkylcyclobutanones in irradiated foods

    NARCIS (Netherlands)

    Horvatovich, Péter; Miesch, Michel; Hasselmann, Claude; Delincée, Henry; Marchioni, Eric

    2005-01-01

    The 2-alkylcyclobutanones (2-ACBs) are formed from triglycerides by irradiation treatment and may be used as markers for this type of food processing. This paper describes a detection method for the analysis of monounsaturated alkyl side chain 2-ACBs, which is formed upon irradiation from monounsatu

  4. Single chain structure of a poly(N-isopropylacrylamide) surfactant in water.

    Science.gov (United States)

    Abbott, Lauren J; Tucker, Ashley K; Stevens, Mark J

    2015-03-01

    We present atomistic simulations of a single PNIPAM-alkyl copolymer surfactant in aqueous solution at temperatures below and above the LCST of PNIPAM. We compare properties of the surfactant with pure PNIPAM oligomers of similar lengths, such as the radius of gyration and solvent accessible surface area, to determine the differences in their structures and transition behavior. We also explore changes in polymer-polymer and polymer-water interactions, including hydrogen bond formation. The expected behavior is observed in the pure PNIPAM oligomers, where the backbone folds onto itself above the LCST in order to shield the hydrophobic groups from water. The surfactant, on the other hand, does not show much conformational change as a function of temperature, but instead folds to bring the hydrophobic alkyl tail and PNIPAM headgroup together at all temperatures. The atomic detail available from these simulations offers important insight into understanding how the transition behavior is changed in PNIPAM-based systems.

  5. Optimization of Biodegradability and Toxicity Testing of Degradation Product from Linear Alkyl BenzeneSulfonate (LAS) Surfactant as Cleaning Detergent Agent

    OpenAIRE

    2009-01-01

    Optimization of Biodegradability and Toxicity Testing of Degradation Product from Linear Alkyl BenzeneSulfonate (LAS) Surfactant as Cleaning Detergent Agent. Linear Alkyl Benzene Sulfonate (LAS) is a surfactantused in laundry detergent as cleaning agent and toxic to aquatic organisms. Results shows, with the LAS concentrationused (20 ppm) in medium, adaptation time and Acinetobacter sp. growth has shown better biodegradation ability thanthree other bacteria used Pseudomonas putida, Pseudomona...

  6. Conformation-specific spectroscopy of alkyl benzyl radicals: Effects of a radical center on the CH stretch infrared spectrum of an alkyl chain

    Science.gov (United States)

    Korn, Joseph A.; Tabor, Daniel P.; Sibert, Edwin L.; Zwier, Timothy S.

    2016-09-01

    An important initial step in the combustion of gasoline and diesel fuels is the abstraction of hydrogen from alkylbenzenes to form resonance-stabilized alkyl benzyl radicals. This work uses, for the first time, double resonance spectroscopy methods to explore the conformation-specific vibronic and infrared spectroscopy of the α-ethylbenzyl (αEtBz) and α-propylbenzyl (αPrBz) radicals. Local mode Hamiltonian modeling enables assignment of the alkyl CH stretch IR spectra, accounting for Fermi resonance that complicates aliphatic alkyl CH stretch IR spectroscopy. The ground state conformational preferences of the ethyl and propyl chains are changed from those in the alkylbenzenes themselves, with global minima occurring for an in-plane orientation of the alkyl chain (trans) about its first dihedral angle (ϕf123, numbers are alkyl C atoms. C1 is CH radical site). This in-plane structure is the only observed conformer for the α-EtBz radical, while two conformers, tt and tg' share this orientation at the first dihedral, but differ in the second (ϕ1234) for the αPrBz radical. The in-plane orientation lowers the local site frequencies of the CH2 group stretches immediately adjacent to the benzylic radical site by about 50 cm-1 relative to those in pure alkyl chains or alkylbenzenes. This effect of the radical site is localized on the first CH2 group, with little effect on subsequent members of the alkyl chain. In the D1 excited electronic state, an out-of-plane orientation is preferred for the alkyl chains, leading to torsional mode Franck-Condon activity in the D0-D1 spectra that is both conformer-specific and diagnostic of the conformational change.

  7. The effect of the cation alkyl chain branching on mutual solubilities with water and toxicities

    Science.gov (United States)

    Kurnia, Kiki A.; Sintra, Tânia E.; Neves, Catarina M. S. S.; Shimizu, Karina; Lopes, José N. Canongia; Gonçalves, Fernando; Ventura, Sónia P. M.; Freire, Mara G.; Santos, Luís M. N. B. F.; Coutinho, João A. P.

    2014-01-01

    The design of ionic liquids has been focused on the cation-anion combinations but other more subtle approaches can be used. In this work the effect of the branching of the cation alkyl chain on the design of ionic liquids (ILs) is evaluated. The mutual solubilities with water and toxicities of a series of bis(trifluoromethylsulfonyl)-based ILs, combined with imidazolium, pyridinium, pyrrolidinium, and piperidinium cations with linear or branched alkyl chains, are reported. The mutual solubility measurements were carried out in the temperature range from (288.15 to 323.15) K. From the obtained experimental data, the thermodynamic properties of the solution (in the water-rich phase) were determined and discussed. The COnductor like Screening MOdel for Real Solvents (COSMO-RS) was used to predict the liquid-liquid equilibrium. Furthermore, molecular dynamic simulations were also carried out aiming to get a deeper understanding of these fluids at the molecular level. The results show that the increase in the number of atoms at the cation ring (from five to six) leads to a decrease in the mutual solubilities with water while increasing their toxicity, and as expected from the well-established relationship between toxicities and hydrophobicities of ILs. The branching of the alkyl chain was observed to decrease the water solubility in ILs, while increasing the ILs solubility in water. The inability of COSMO-RS to correctly predict the effect of branching alkyl chains toward water solubility on them was confirmed using molecular dynamic simulations to be due to the formation of nano-segregated structures of the ILs that are not taken into account by the COSMO-RS model. In addition, the impact of branched alkyl chains on the toxicity is shown to be not trivial and to depend on the aromatic nature of the ILs. PMID:25119425

  8. Synthesis and properties of di-n-dodecyl alpha,omega-alkyl bisphosphate surfactants

    NARCIS (Netherlands)

    Duivenvoorde, F.L.; Feiters, M.C.; Van der Gaast, S.J.; Engberts, J.B.F.N.

    1997-01-01

    Three gemini and two bolaform bisphosphate surfactants of the type 12-s-12, with s = 6, 8, 12, 18, and 24 carbon atoms, have been synthesized and their aggregation behavior has been studied. The bolaform surfactants 12-18-12 and 12-24-12 were found to form vesicles in aqueous solution, as indicated

  9. Synthesis and properties of di-n-dodecyl alpha,omega-alkyl bisphosphate surfactants

    NARCIS (Netherlands)

    Duivenvoorde, F.L.; Feiters, M.C.; Van der Gaast, S.J.; Engberts, J.B.F.N.

    1997-01-01

    Three gemini and two bolaform bisphosphate surfactants of the type 12-s-12, with s = 6, 8, 12, 18, and 24 carbon atoms, have been synthesized and their aggregation behavior has been studied. The bolaform surfactants 12-18-12 and 12-24-12 were found to form vesicles in aqueous solution, as indicated

  10. Superhydrophilic surfaces from short and medium chain solvo-surfactants

    Directory of Open Access Journals (Sweden)

    Valentin Romain

    2013-01-01

    Full Text Available Pure monoglycerides (GM-Cs and glycerol carbonate esters (GCE-Cs are two families of oleochemical molecules composed of a polar part, glycerol for GM-Cs, glycerol carbonate for GCE-Cs, and a fatty acid lipophilic part. From a chemical point of view, GM-Cs include two free oxygen atoms in the hydroxyl functions and one ester function between the fatty acid and the glycerol parts. GCE-Cs contain two blocked oxygen atoms in the cyclic carbonate backbone and three esters functions: two endocyclic in the five-membered cyclic carbonate function, one exocyclic between the fatty acid and glycerol carbonate parts. At the physico-chemical level, GMCs and GCE-Cs are multifunctional molecules with amphiphilic structures: a common hydrophobic chain to the both families and a polar head, glycerol for GMs and glycerol carbonate for GCE-Cs. Physicochemical properties depend on chain lengths, odd or even carbon numbers on the chain, and glyceryl or cyclocarbonic polar heads. The solvo-surfactant character of GM-Cs and overall GCE-Cs were discussed through the measurements of critical micellar concentration (CMC or critical aggregation concentration (CAC. These surface active glycerol esters/glycerol carbonate esters were classified following their hydrophilic/hydrophobic character correlated to their chain length (LogPoctanol/water = f(atom carbon number. Differential scanning calorimetry and optical polarized light microscopy allow us to highlight the selfassembling properties of the glycerol carbonate esters alone and in presence of water. We studied by thermal analysis the polymorphic behaviour of GCE-Cs, and the correlation between their melting points versus the chain lengths. Coupling the self-aggregation and crystallization properties, superhydrophilic surfaces were obtained by formulating GM-Cs and GCE-Cs. An efficient durable water-repellent coating of various metallic and polymeric surfaces was allowed. Such surfaces coated by self-assembled fatty acid

  11. Effect of Alkyl Chain Length and Unsaturation of the Phospholipid on the Physicochemical Properties of Lipid Nanoparticles.

    Science.gov (United States)

    Funakoshi, Yuka; Iwao, Yasunori; Noguchi, Shuji; Itai, Shigeru

    2015-01-01

    Previously, we developed lipid nanoparticles (LNs) containing poorly water-soluble drugs using two types of phospholipids, a neutral phospholipid (hydrogenated soybean phosphatidylcholine) and a negatively-charged phospholipid (dipalmitoylphosphatidylglycerol), with mean particle sizes of less than 100 nm. Here, we studied the effects of alkyl chain length and unsaturation of neutral and negatively-charged phospholipids on the physicochemical properties of LNs. Three neutral phospholipids, dimyristoylphosphatidylcholine, dipalmitoylphosphatidylcholine and distearoylphosphatidylcholine, having different alkyl chain lengths, were compared. The mean particle size of the LNs increased with the alkyl chain length, while the concentration of the drug entrapped in the LNs decreased. The particle size of all of the LNs could be maintained at less than 100 nm for 1 month in cool and dark conditions, with the LNs with longer alkyl chain lipids showing greater stability. In the unsaturated phospholipids, the double bond in the alkyl chain of dioleoylphosphatidylcholine and dierucoylphosphatidylcholine did not affect the physicochemical properties of the LNs. The negatively-charged phospholipids dipalmitoylphosphatidylglycerol and distearoylphosphatidylglycerol were also compared; LNs with longer alkyl chain lipids had larger particle sizes and lower drug concentrations, similar to the results for neutral phospholipids. We concluded that although some changes in physicochemical properties were observed among LNs with different phospholipid alkyl chain lengths, this methodology was general. LNs with suitable physicochemical properties could be prepared irrespective of the type of phospholipids used.

  12. Construction of higher-ordered monolayer membranes derived from archaeal membrane lipid-inspired cyclic lipids with longer alkyl chains.

    Science.gov (United States)

    Nakamura, Makoto; Goto, Rie; Tadokoro, Toshio; Shibakami, Motonari

    2007-06-15

    A series of artificial cyclic lipids that mimic archaeal membrane ones has been synthesized. The structural features of these molecules include a longer cyclic framework, in which the alkyl chain length ranges from 24 to 32 in carbon number, which is longer than our first analogous molecule with 20-carbon long alkyl chains [K. Miyawaki, T. Takagi, M. Shibakami, Synlett 8 (2002) 1326]. Microscopic observation reveals that these molecules have a self-assembling ability: hydration of the lipids yields multilamellar vesicles in aqueous solution and monolayer sheets on solid supports. High-sensitivity differential scanning calorimetry (24- and 28-carbon alkyl chain lipids) indicates that (i) the alkyl chain length affects their phase behavior and (ii) the enthalpies of endothermic peaks accompanied by phase transition were considerably lower than those of their monomeric phospholipid analogs. Fluorescence polarization measurements suggest that the membranes made from the 24-carbon alkyl chain lipid have a higher polarization factor than membranes composed of DMPC and DMPC plus cholesterol. These findings imply that the cyclic lipids containing 24- and 28-carbon alkyl chain construct well-organized monolayer membranes and, in particular, that the molecular order of the 24-carbon alkyl chain lipid is higher than that of bilayer membranes in the liquid-ordered phase.

  13. Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an alpha,omega-diamino-(oxa)alkyl spacer

    NARCIS (Netherlands)

    Wagenaar, Anno; Engberts, Jan B. F. N.

    2007-01-01

    Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic

  14. Synthesis of nonionic reduced-sugar based bola amphiphiles and gemini surfactants with an alpha,omega-diamino-(oxa)alkyl spacer

    NARCIS (Netherlands)

    Wagenaar, Anno; Engberts, Jan B. F. N.

    2007-01-01

    Reduced-sugar based gemini surfactants with an alpha,omega-diamino-(oxa) alkyl spacer exhibit a rich pH-dependent aggregation behavior and are efficient DNA carriers in gene transfection. Herein, we describe an improved synthetic procedure for these amphiphiles. First, a series of novel nonionic bol

  15. Photocurrent enhancement from diketopyrrolopyrrole polymer solar cells through alkyl-chain branching point manipulation.

    Science.gov (United States)

    Meager, Iain; Ashraf, Raja Shahid; Mollinger, Sonya; Schroeder, Bob C; Bronstein, Hugo; Beatrup, Daniel; Vezie, Michelle S; Kirchartz, Thomas; Salleo, Alberto; Nelson, Jenny; McCulloch, Iain

    2013-08-07

    Systematically moving the alkyl-chain branching position away from the polymer backbone afforded two new thieno[3,2-b]thiophene-diketopyrrolopyrrole (DPPTT-T) polymers. When used as donor materials in polymer:fullerene solar cells, efficiencies exceeding 7% were achieved without the use of processing additives. The effect of the position of the alkyl-chain branching point on the thin-film morphology was investigated using X-ray scattering techniques and the effects on the photovoltaic and charge-transport properties were also studied. For both solar cell and transistor devices, moving the branching point further from the backbone was beneficial. This is the first time that this effect has been shown to improve solar cell performance. Strong evidence is presented for changes in microstructure across the series, which is most likely the cause for the photocurrent enhancement.

  16. Removal of phase transfer agent leads to restricted dynamics of alkyl chains in monolayer protected clusters

    Indian Academy of Sciences (India)

    V R Rajeev Kumar; R Mukhopadhyay; T Pradeep

    2008-11-01

    The effect of phase transfer agent in the dynamics of monolayer protected gold nanoparticles has been investigated by infrared (IR) and nuclear magnetic resonance (NMR) spectroscopies. The experiments were performed with octadecane thiol and dodecane thiol protected gold nanoparticles. The materials prepared were characterized by UV-Visible spectroscopy, transmission electron microscopy and IR spectroscopy. Repeated purification of the monolayer protected gold clusters made the alkyl chains defect-free. Such effects are reflected in the infrared spectra. Interdigitation of the monolayers that followed the purification leads to alkyl chains with limited mobility. This was reflected in 13C and 1H NMR linewidths. The NMR measurements indicate that the removal of phase transfer agent affects the dynamics of isolated clusters and those with interdigitated monolayers in different ways.

  17. Long Alkyl Chain Organophosphorus Coupling Agents for in Situ Surface Functionalization by Reactive Milling

    Directory of Open Access Journals (Sweden)

    Annika Betke

    2014-08-01

    Full Text Available Innovative synthetic approaches should be simple and environmentally friendly. Here, we present the surface modification of inorganic submicrometer particles with long alkyl chain organophosphorus coupling agents without the need of a solvent, which makes the technique environmentally friendly. In addition, it is of great benefit to realize two goals in one step: size reduction and, simultaneously, surface functionalization. A top-down approach for the synthesis of metal oxide particles with in situ surface functionalization is used to modify titania with long alkyl chain organophosphorus coupling agents. A high energy planetary ball mill was used to perform reactive milling using titania as inorganic pigment and long alkyl chain organophosphorus coupling agents like dodecyl and octadecyl phosphonic acid. The final products were characterized by IR, NMR and X-ray fluorescence spectroscopy, thermal and elemental analysis as well as by X-ray powder diffraction and scanning electron microscopy. The process entailed a tribochemical phase transformation from the starting material anatase to a high-pressure modification of titania and the thermodynamically more stable rutile depending on the process parameters. Furthermore, the particles show sizes between 100 nm and 300 nm and a degree of surface coverage up to 0.8 mmol phosphonate per gram.

  18. Ultrasonic Relaxation Study of 1-Alkyl-3-methylimidazolium-Based Room-Temperature Ionic Liquids: Probing the Role of Alkyl Chain Length in the Cation.

    Science.gov (United States)

    Zorębski, Michał; Zorębski, Edward; Dzida, Marzena; Skowronek, Justyna; Jężak, Sylwia; Goodrich, Peter; Jacquemin, Johan

    2016-04-14

    Ultrasound absorption spectra of four 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imides were determined as a function of the alkyl chain length on the cation from 1-propyl to 1-hexyl from 293.15 to 323.15 K at ambient pressure. Herein, the ultrasound absorption measurements were carried out using a standard pulse technique within a frequency range from 10 to 300 MHz. Additionally, the speed of sound, density, and viscosity have been measured. The presence of strong dissipative processes during the ultrasound wave propagation was found experimentally, i.e., relaxation processes in the megahertz range were observed for all compounds over the whole temperature range. The relaxation spectra (both relaxation amplitude and relaxation frequency) were shown to be dependent on the alkyl side chain length of the 1-alkyl-3-methylimidazolium ring. In most cases, a single-Debye model described the absorption spectra very well. However, a comparison of the determined spectra with the spectra of a few other imidazolium-based ionic liquids reported in the literature (in part recalculated in this work) shows that the complexity of the spectra increases rapidly with the elongation of the alkyl chain length on the cation. This complexity indicates that both the volume viscosity and the shear viscosity are involved in relaxation processes even in relatively low frequency ranges. As a consequence, the sound velocity dispersion is present at relatively low megahertz frequencies.

  19. Thermodynamic Interactions between Polystyrene and Long-Chain Poly(n-Alkyl Acrylates) Derived from Plant Oils.

    Science.gov (United States)

    Wang, Shu; Robertson, Megan L

    2015-06-10

    Vegetable oils and their fatty acids are promising sources for the derivation of polymers. Long-chain poly(n-alkyl acrylates) and poly(n-alkyl methacrylates) are readily derived from fatty acids through conversion of the carboxylic acid end-group to an acrylate or methacrylate group. The resulting polymers contain long alkyl side-chains with around 10-22 carbon atoms. Regardless of the monomer source, the presence of alkyl side-chains in poly(n-alkyl acrylates) and poly(n-alkyl methacrylates) provides a convenient mechanism for tuning their physical properties. The development of structured multicomponent materials, including block copolymers and blends, containing poly(n-alkyl acrylates) and poly(n-alkyl methacrylates) requires knowledge of the thermodynamic interactions governing their self-assembly, typically described by the Flory-Huggins interaction parameter χ. We have investigated the χ parameter between polystyrene and long-chain poly(n-alkyl acrylate) homopolymers and copolymers: specifically we have included poly(stearyl acrylate), poly(lauryl acrylate), and their random copolymers. Lauryl and stearyl acrylate were chosen as model alkyl acrylates derived from vegetable oils and have alkyl side-chain lengths of 12 and 18 carbon atoms, respectively. Polystyrene is included in this study as a model petroleum-sourced polymer, which has wide applicability in commercially relevant multicomponent polymeric materials. Two independent methods were employed to measure the χ parameter: cloud point measurements on binary blends and characterization of the order-disorder transition of triblock copolymers, which were in relatively good agreement with one another. The χ parameter was found to be independent of the alkyl side-chain length (n) for large values of n (i.e., n > 10). This behavior is in stark contrast to the n-dependence of the χ parameter predicted from solubility parameter theory. Our study complements prior work investigating the interactions between

  20. U-shaped conformation of alkyl chains bound to a synthetic receptor cucurbit[8]uril.

    Science.gov (United States)

    Ko, Young Ho; Kim, Youngkook; Kim, Hyunuk; Kim, Kimoon

    2011-02-01

    The behavior of a series of alkanes bound to the molecular host cucurbit[8]uril (CB[8]) has been systematically studied by 2D (1)H NMR spectroscopy and isothermal titration calorimetry (ITC). CB[8] and alkyltrimethylammonium (C(m) TA(+), (CH(3))(3)N(+)C(m)H(2m+1), m=6-16) form 1:1 host-guest complexes with a high binding constant (K≈10(6) m(-1)). The shortest hexyl chain of C(6)TA(+) can be fully encapsulated in an extended conformation inside the CB[8] cavity, which is driven by both enthalpy and entropy. However, for the longer aliphatic chains, C(8)-C(16), the long alkyl tails take a U-shaped conformation inside the cavity, and their complexation is dominantly or almost exclusively enthalpy-driven, owing to the increased van der Waals contact between the folded aliphatic chain and the inner wall of the host cavity. As the chain length increases from C(8) to C(16), the ammonium head group of the guests moves away from the portal of CB[8] while the long aliphatic tails maintain the U-shaped conformation inside the cavity. The complexation of C(m)TA(+) with CB[8] follows the enthalpy-entropy compensation rule commonly observed in molecular recognition systems. For example, among the guest molecules, C(12)TA(+) shows the highest enthalpic gain (most favorable), owing to the large van der Waals contact between the guest and the host cavity, and at the same time the most unfavorable entropic contribution, owing to the severe conformational restriction of the U-shaped alkyl chain inside the host. The enthalpy-entropy compensation plot for the complexation suggests large conformational changes of the long alkyl chains and extensive dehydration associated with the inclusion complex formation.

  1. Nanostructures and Self-Assembly of Organogels via Benzimidazole/Benzothiazole Imide Derivatives with Different Alkyl Substituent Chains

    Directory of Open Access Journals (Sweden)

    Xihai Shen

    2013-01-01

    Full Text Available New benzimidazole/benzothiazole imide derivatives with different alkyl substituent chains were designed and synthesized. Their gelation behaviors in 22 solvents were tested as novel low-molecular-mass organic gelators. The test showed that the alkyl substituent chains and headgroups of benzimidazole/benzothiazole residues in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. More alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. SEM and AFM observations revealed that the gelator molecules self-assemble into different aggregates from wrinkle, lamella and belt to dot with change of solvents. Spectral studies indicated that there existed different H-bond formation between imide groups and hydrophobic force of alkyl substituent chains in molecular skeletons. The present work may give some insights into design and character of new organogelators and soft materials with special molecular structures.

  2. Synthesis and properties of di-n-dodecyl alpha,omega-alkyl bisphosphate surfactants

    OpenAIRE

    1997-01-01

    Three gemini and two bolaform bisphosphate surfactants of the type 12-s-12, with s = 6, 8, 12, 18, and 24 carbon atoms, have been synthesized and their aggregation behavior has been studied. The bolaform surfactants 12-18-12 and 12-24-12 were found to form vesicles in aqueous solution, as indicated by electron microscopy. The geminis 12-6-12, 12-8-12, and 12-12-12 form micellar structures. The cmc's of the geminis, obtained from conductivity measurements, spectroscopic methods, and microcalor...

  3. Dynamics of alkyl chains in monolayer protected metal clusters and their superlattices

    Energy Technology Data Exchange (ETDEWEB)

    Mukhopadhyay, R [Solid State Physics Division, BARC, Mumbai 400085 (India); Mitra, S [Solid State Physics Division, BARC, Mumbai 400085 (India); Johnson, M [Institute Lau-Langevin, BP156, F-38042, Grenoble, Cedex 9 (France); Pradeep, T [Department of Chemistry and SAIF, IITm, Chennai 600 036 (India)

    2007-12-15

    Alkyl chains dynamics in monolayer protected metal cluster (MPC) systems of gold and silver have been studied by the quasielastic neutron scattering (QENS) technique. Isolated MPCs investigated are 6, 12 and 18 carbon n-alkyl chain thiolate protected 4 nm diameter gold clusters while the superlattices are their silver analogues. Evolution of dynamics with temperature is found to be very different in the isolated clusters and their superlattices. While continuous evolution of the dynamics of the monolayer was observed in isolated MPCs, it is abrupt in superlattice systems and occurs at a temperature consistent with the superlattice melting detected in calorimetry measurements. A model where the chain undergoes uniaxial rotational diffusion with additional body axis fluctuation was found to describe the data consistently. For the superlattice systems, the chains are found to be held by strong inter-chain interactions below the superlattice melting. The data from the planar silver thiolate systems show similar behavior like the superlattice systems, consistent with the calorimetric data.

  4. Dynamic Study of Gemini Surfactant and Single-chain Surfactant at Air/Water Interface

    Institute of Scientific and Technical Information of China (English)

    Yi Jian CHEN; Gui Ying XU; Shi Ling YUAN; Hai Ying SUN

    2005-01-01

    Molecular dynamics (MD) simulation are used to study the properties of gemini surfactant of ethyl-α,ω-bis(dodecyldimethylammonium bromide) (C12C2C12) and dodecyltrimethylammonium bromide (DTAB) at the air/water interface, respectively. In the two systems,the surfactant concentrations are both 28 wt. %, and other conditions are also the same. After reaching the thermodynamic equilibrium, the concentration profiles, the radial distributions functions (RDF) and the mean squared displacement (MSD) are investigated. Theresults reveal that the surface activity of C12C2C12 suffactant is higher than DTAB surfactant.

  5. Structural isomers of polyfluorinated di- and tri-alkylated phosphate ester surfactants present in industrial blends and in microwave popcorn bags.

    Science.gov (United States)

    Trier, Xenia; Nielsen, Nikoline Juul; Christensen, Jan H

    2011-09-01

    In this study, we provide strategies for detecting and quantifying the structural isomers of polyfluorinated di- and tri-alkyl surfactants (PFAS) by mass spectrometry (MS). We specifically investigate polyfluorinated dialkylated phosphate ester surfactants (x:2/y:2 diPAPS, (F(CF(2))( x )CH(2)CH(2)O-P(O)(O)(-)-OCH(2)CH(2)(CF(2))( y )F)) and their thioether analogues (x:2/y:2 S-diPAPS, F(CF(2))( x )CH(2)CH(2)SCH(2)-C[CH(2)O)(2)P(O)(O)(-)]-CH(2)SCH(2)CH(2)(CF(2))( y )F), which are used for industrial applications, such as oil- and water-repellent coatings on paper and board. DiPAPS have been found in human blood and are metabolised to the persistent perfluoroalkyl carboxylic acids (PFCA) in rats. A microwave popcorn bag extract was analysed by ultrahigh-pressure liquid chromatography coupled to a negative electrospray ionisation-quadrupole time-of-flight MS. The extract contained S-diPAPS, diPAPS and trialkylated (triPAPS) impurities. TriPAPS were also present in industrial and synthetic diPAPS standards, and were verified with an 8:2/8:2/8:2 triPAPS standard. The eight elemental compositions (m/z's) of diPAPS in the extract represent 19 precursor ion structures, and the six S-diPAPS m/z's represent at least 13 structures. The diPAPS had [M-H](-) precursor ions of m/z 789, 889,…1,489 and the S-diPAPS of m/z 921, 1,021,…1,421, corresponding to fluorinated chains from C(6-18). Each m/z appeared as one to three chromatographic peaks of structural isomers, where, e.g. m/z 1,189 was present as 10:2/10:2, 8:2/12:2 and 6:2/14:2 diPAPS. The isomers formed different products ions, thus only half of the m/z 1,189 diPAPS concentration was measured with one precursor ion > product ion transition. In general, knowledge about structural isomers of poly-alkylated PFAS is needed for the estimation of types and amounts of perfluorinated degradation products, such as PFCA from diPAPS.

  6. Comparative Study of the Intermolecular Dynamics and Physical Properties of Branched and Linear Alkyl Chain Imidazolium Ionic Liquids

    Science.gov (United States)

    Xue, Lianjie; Bardak, Fehmi; Tamas, George; Gurung, Eshan; Quitevis, Edward; Koh, Yung; Simon, Sindee

    2014-03-01

    The optical Kerr effect (OKE) spectra, densities, viscosities, and transition temperatures of 1-alkyl-3-methylimidazolium bis{(trifluoromethane)sulfonyl}amide ionic liquids (ILs) with branched alkyl chains, -Cn-3CH(CH3)2 (branched ILs), were measured and compared to those with linear alkyl chains, -Cn-1CH3 (linear ILs), for n = 3, 4, 5, 6 and 7. The results show that a branched IL has a higher viscosity and transition temperature Tg than the corresponding linear IL with the same n, whereas the densities of each branched/linear IL pair are the same within experimental error. For short alkyl chains (n =3 and 4) the intermolecular part of the OKE spectrum of the branched ILs tends to be narrower and lower in frequency than that of the linear ILs. This suggests that branching softens the intermolecular modes. For long alkyl chains (n =5-7), the difference between the intermolecular spectrum of the branched IL and that of the linear IL with the same n decreases, which indicates that the branching effect becomes smaller when the alkyl chains get longer. This work was supported by NSF grant CHE-1153077.

  7. Modification of nano-sized layered double hydroxides by long-chain organic aliphatic surfactants

    Directory of Open Access Journals (Sweden)

    RAMASAMY ANBARASAN

    2008-03-01

    Full Text Available The inter-layer anion of layered double hydroxides (LDH with a hydrotalcite (HT-like structure was ion-exchanged with various organic surfactants, particularly with long chain aliphatic surfactants. After the ion-exchange process, the basal spacing of the LDH was increased and the increase of the basal spacing depended on various factors, such as the intercalation capacity functionality and orientation capability of the surfactant. Of the employed surfactants, stearic acid intercalated LDH showed the highest increase of the basal spacing, which was confirmed by XRD analysis. FTIR results supported the interaction of the surfactants with the LDH. In addition, an increase in the thermal stability of the dodecanedioic acid intercalated HT was evidenced by the TGA method.

  8. Fate and effects of amphoteric surfactants in the aquatic environment.

    Science.gov (United States)

    Garcia, M Teresa; Campos, Encarna; Marsal, Agustí; Ribosa, Isabel

    2008-10-01

    Amphoteric surfactants form part of specialty surfactants available for formulators to improve or design new formulations in response to environmental, toxicity, safety and performance demands. Nevertheless, limited information on the ecological properties of amphoterics is available. In the present work, the aerobic and anaerobic biodegradability and the aquatic toxicity of different types of amphoteric surfactants (three alkyl betaines, one alkylamido betaine and three alkyl imidazoline derivatives) were studied. The amphoteric surfactants tested were readily biodegradable under aerobic conditions (CO2 headspace test) and alkylamido betaines and alkyl imidazoline derivatives were also easily biodegradable under anaerobic conditions (test based on the ECETOC method). Toxicity to Photobacterium phosphoreum and Daphnia magna increased with the fatty chain length of the surfactant. The EC50 toxicity values of the amphoterics tested were higher than 5 mg/L, and alkyl imidazoline derivatives, with EC50 values from 20 to > 200 mg/L, showed the lowest aquatic toxicity.

  9. Physicochemistry and percolation behavior of microemulsions as a function of chain length of cosurfactant and surfactant

    Directory of Open Access Journals (Sweden)

    Purva Thatai

    2015-03-01

    Full Text Available The study involved investigations on phase behavior and physicochemical characterization of microemulsions (MEs stabilized by mixture containing polysorbates (C12-C18 as surfactants and n-alkanols (C2-C6 as cosurfactant. Distribution coefficient and Gibbs free energy were also determined for systems containing Tween 20 as surfactant. ME having Tween 20 as surfactant and ethanol as cosurfactant was found to exhibit maximium ME region as well as water solubilization capacity (WSC. Values of both these parameters were found to decrease as chain length of surfactant increased in all cases of alkanols with exception of Tween 80. This could be attributed to unsaturated structure of Tween 80 which presumably caused folding of chain and lesser oil penetration. Furthermore, the transition of w/o MEs to o/w MEs via bicontinuous structure along the dilution line was confirmed by conductivity, viscosity and droplet size analysis.

  10. Hydrophobic, electrostatic, and dynamic polymer forces at silicone surfaces modified with long-chain bolaform surfactants.

    Science.gov (United States)

    Rapp, Michael V; Donaldson, Stephen H; Gebbie, Matthew A; Das, Saurabh; Kaufman, Yair; Gizaw, Yonas; Koenig, Peter; Roiter, Yuri; Israelachvili, Jacob N

    2015-05-06

    Surfactant self-assembly on surfaces is an effective way to tailor the complex forces at and between hydrophobic-water interfaces. Here, the range of structures and forces that are possible at surfactant-adsorbed hydrophobic surfaces are demonstrated: certain long-chain bolaform surfactants-containing a polydimethylsiloxane (PDMS) mid-block domain and two cationic α, ω-quarternary ammonium end-groups-readily adsorb onto thin PDMS films and form dynamically fluctuating nanostructures. Through measurements with the surface forces apparatus (SFA), it is found that these soft protruding nanostructures display polymer-like exploration behavior at the PDMS surface and give rise to a long-ranged, temperature- and rate-dependent attractive bridging force (not due to viscous forces) on approach to a hydrophilic bare mica surface. Coulombic interactions between the cationic surfactant end-groups and negatively-charged mica result in a rate-dependent polymer bridging force during separation as the hydrophobic surfactant mid-blocks are pulled out from the PDMS interface, yielding strong adhesion energies. Thus, (i) the versatile array of surfactant structures that may form at hydrophobic surfaces is highlighted, (ii) the need to consider the interaction dynamics of such self-assembled polymer layers is emphasized, and (iii) it is shown that long-chain surfactants can promote robust adhesion in aqueous solutions.

  11. Effect of alkyl chain length and temperature on the thermodynamic properties of ionic liquids 1-alkyl-3-methylimidazolium bromide in aqueous and non-aqueous solutions at different temperatures

    Energy Technology Data Exchange (ETDEWEB)

    Sadeghi, Rahmat [Department of Chemistry, University of Kurdistan, Sanandaj (Iran, Islamic Republic of)], E-mail: rahsadeghi@yahoo.com; Shekaari, Hemayat [Department of Chemistry, Faculty of Science, University of Mohaghegh Ardabili, Ardabil (Iran, Islamic Republic of); Hosseini, Rahim [Department of Chemistry, University of Kurdistan, Sanandaj (Iran, Islamic Republic of)

    2009-02-15

    The alkyl chain length of 1-alkyl-3-methylimidazolium bromide ([Rmim][Br], R = propyl (C{sub 3}), hexyl (C{sub 6}), heptyl (C{sub 7}), and octyl (C{sub 8})) was varied to prepare a series of room-temperature ionic liquids (RTILs), and experimental measurements of density and speed of sound at different temperatures ranging from (288.15 to 308.15) K for their aqueous and methanolic solutions in the dilute concentration region (0.01 to 0.30) mol . kg{sup -1} were taken. The values of the compressibilities, expansivity and apparent molar properties for [C{sub n}mim][Br] in aqueous and methanolic solutions were determined at the investigated temperatures. The obtained apparent molar volumes and apparent molar isentropic compressibilities were fitted to the Redlich-Mayer and the Pitzer's equations from which the corresponding infinite dilution molar properties were obtained. The values of the infinite dilution molar properties were used to obtain some information about solute-solvent and solute-solute interactions. The thermodynamic properties of investigated ionic liquids in aqueous solutions have been compared with those in methanolic solutions. Also, the comparison between thermodynamic properties of investigated solutions and those of electrolyte solutions, polymer solutions, cationic surfactant solutions and tetraalkylammonium salt solutions have been made.

  12. Alkyl chain length-dependent surface reaction of dodecahydro-N-alkylcarbazoles on Pt model catalysts

    Energy Technology Data Exchange (ETDEWEB)

    Gleichweit, Christoph; Amende, Max; Bauer, Udo; Schernich, Stefan; Höfert, Oliver; Lorenz, Michael P. A.; Zhao, Wei; Bachmann, Philipp; Papp, Christian, E-mail: christian.papp@fau.de [Lehrstuhl für Physikalische Chemie II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Müller, Michael; Koch, Marcus [Lehrstuhl für Chemische Reaktionstechnik, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Wasserscheid, Peter [Lehrstuhl für Chemische Reaktionstechnik, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Erlangen Catalysis Resource Center, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Libuda, Jörg; Steinrück, Hans-Peter [Lehrstuhl für Physikalische Chemie II, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany); Erlangen Catalysis Resource Center, Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058 Erlangen (Germany)

    2014-05-28

    The concept of liquid organic hydrogen carriers (LOHC) holds the potential for large scale chemical storage of hydrogen at ambient conditions. Herein, we compare the dehydrogenation and decomposition of three alkylated carbazole-based LOHCs, dodecahydro-N-ethylcarbazole (H{sub 12}-NEC), dodecahydro-N-propylcarbazole (H{sub 12}-NPC), and dodecahydro-N-butylcarbazole (H{sub 12}-NBC), on Pt(111) and on Al{sub 2}O{sub 3}-supported Pt nanoparticles. We follow the thermal evolution of these systems quantitatively by in situ high-resolution X-ray photoelectron spectroscopy. We show that on Pt(111) the relevant reaction steps are not affected by the different alkyl substituents: for all LOHCs, stepwise dehydrogenation to NEC, NPC, and NBC is followed by cleavage of the C–N bond of the alkyl chain starting at 380–390 K. On Pt/Al{sub 2}O{sub 3}, we discern dealkylation on defect sites already at 350 K, and on ordered, (111)-like facets at 390 K. The dealkylation process at the defects is most pronounced for NEC and least pronounced for NBC.

  13. Continuous reaction performances of benzene alkylation with long chain olefins catalyzed by ionic liquid

    Institute of Scientific and Technical Information of China (English)

    Congzhen QIAO; Chengyue LI

    2008-01-01

    Based on a compulsive mixing-reacting-sepa-rating-recycling small experimental setup,the continuous reaction performances of benzene alkylation with long chain olefins catalyzed by [BMIM]Cl-AlCl3 ionic liquid were investigated. Three different situations including normal continuous operation mode (reagent materials), sidetrack feeding from different axial positions along the static mixing reactor (reagent materials) and normal con-tinuous alkylation using industrial paraffin and olefins materials were examined. Even under the relatively hype-critical reaction conditions, the single pass conversion of pure 1-dodecene could reach to nearly 100.0%, and the selectivity of 2-phenyl isomer was higher than 37.7%. Although the positions along the reactor for sidetrack feeding were different, the 100.0% single pass conversion of 1-dodecene was also attained before the outlet of the reactor. The refined industrial olefins as raw material could meet with the requirements of continuous alkyla-tion. The influences of impurities such as di-olefins and non-benzene aromatics on the catalytic activity and stability should be studied further.

  14. Catalytic etherification of glycerol with short chain alkyl alcohols in the presence of Lewis acids

    OpenAIRE

    Liu, Fei; De Oliveira Vigier, Karine; Pera-Titus, M.; Pouilloux, Yannick; Clacens, Jean-Marc; De Campo, Floryan; Jérôme, François

    2013-01-01

    International audience; Here we report the homogeneously-catalyzed etherification of glycerol with short chain alkyl alcohols. Among the large variety of Brønsted and Lewis acids tested, we show here that metal triflates are not only the most active but are also capable of catalyzing this reaction with an unprecedented selectivity. In particular, in the presence of Bi(OTf )3, the targeted monoalkylglyceryl ethers were obtained with up to 70% yield. Although tested Brønsted acids were also cap...

  15. Synthesis and Properties of Poly(Isothianaphthene Methines with Chiral Alkyl Chain

    Directory of Open Access Journals (Sweden)

    Hiromasa Goto

    2012-02-01

    Full Text Available We synthesized poly(isothianaphthene methines with chiral alkyl chains in the substituent. Resultant polymers are soluble in THF and CHCl3. Structure of the polymers was characterized with FT-IR, FT-Raman, and UV-Vis-NIR optical absorption spectroscopy. They showed low-bandgap both in solution and in a form of film. Optical activity of the polymers was confirmed with optical rotatory dispersion. Doping effects on the polymer were also examined with UV-Vis-NIR spectroscopy and ESR measurement.

  16. Vapor pressures of 1,3-dialkylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids with long alkyl chains.

    Science.gov (United States)

    Rocha, Marisa A A; Coutinho, João A P; Santos, Luís M N B F

    2014-10-01

    This work presents the vapor pressure at several temperatures for the 1,3-dialkylimidazolium bis(trifluoromethylsulfonyl)imide series, [CN/2CN/2im][NTf2] (N = 14, 16, 18, and 20), measured by a Knudsen effusion method combined with a quartz crystal microbalance. The thermodynamic properties of vaporization of the ionic liquids under study are analysed together with the results obtained previously for the shorter alkyl chain length [CN/2CN/2im][NTf2] (N = 2, 4, 6, 8, 10, and 12), in order to evaluate the effect of the alkyl side chains of the cation and to get additional insights concerning the nanostructuration of ionic liquids. The symmetry effect is explored, based on the comparison with the asymmetric imidazolium based ionic liquids, [CN-1C1im][NTf2]. A trend shift on the thermodynamic properties of vaporization along the alkyl side chains of the extended symmetric ionic liquids, around [C6C6im][NTf2], was detected. An intensification of the odd-even effect was observed starting from [C6C6im][NTf2], with higher enthalpies and entropies of vaporization for the odd numbered ionic liquids, [C7C7im][NTf2] and [C9C9im][NTf2]. Similar, but less pronounced, odd-even effect was found for the symmetric ionic liquids with lower alkyl side chains length, [CN/2CN/2im][NTf2] (with N = 4, 6, 8, 10, and 12). This effect is related with the predominant orientation of the terminal methyl group of the alkyl chain to the imidazolium ring and their influence in the cation-anion interaction. The same Critical Alkyl length at the hexyl, (C6C1and C6C6) was found for both asymmetric and symmetric series indicating that the nanostructuration of the ionic liquids is related with alkyl chain length.

  17. The horizontal transfer of antibiotic resistance genes is enhanced by ionic liquid with different structure of varying alkyl chain length

    Directory of Open Access Journals (Sweden)

    Qing eWang

    2015-08-01

    Full Text Available Antibiotic resistance genes (ARGs have become a global health concern. In our previous study, an ionic liquid (IL 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIm][PF6] had been proven to facilitate the dissemination of ARGs in the environment. However, enhanced alkyl group chain length or the substitution of alkyl groups with the cation ring corresponded with increased antimicrobial effects. In this study, we investigated how different structures of ILs with 4, 6 and 8 C atoms in the longer alkyl chain on the imidazolium cations facilitated the dissemination of ARGs. The promotion of plasmid RP4 transfer frequency decreased with [CnMIM][BF4] increasing the alkyl chain length from 4 carbon atoms to 8 carbon atoms on the imidazolium cations, which is observed with [BMIM][BF4] (n=4, 5.9 fold> HMIM][BF4] (n=6, 2.2 fold> [OMIM][BF4] (n=8, 1.7 fold. This illustrates that [CnMIM][BF4] with increasing the alkyl chain length exert decreasing ability in facilitating plasmid RP4 horizontal transfer, which is possibly related to IL-structure dependent toxicity. The IL-structure dependent plasmid RP4 transfer frequency was attributable to bacterial cell membrane permeability weaken with increasing alkyl chain length of [CnMIM][PF4], which was evidenced by flow cytometry (FCM. In freshwater microcosm, [CnMIm][BF4] promoted the relative abundance of the sulI and intI genes for 4.6 folds, aphA and traF for 5.2 folds higher than the untreated groups, promoting the propagation of ARGs in the aquatic environment. This is the first report that ILs with different structure of varying alkyl chain length facilitate horizontal transfer of plasmid RP4 which is widely distributed in the environment, and thus add the adverse effects of the environmental risk of ILs.

  18. Effect of the alkyl chain length on the rotational dynamics of nonpolar and dipolar solutes in a series of N-alkyl-N-methylmorpholinium ionic liquids.

    Science.gov (United States)

    Khara, Dinesh Chandra; Kumar, Jaini Praveen; Mondal, Navendu; Samanta, Anunay

    2013-05-01

    Rotational dynamics of two dipolar solutes, 4-aminophthalimide (AP) and 6-propionyl-2-dimethylaminonaphthalene (PRODAN), and a nonpolar solute, anthracene, have been studied in N-alkyl-N-methylmorpholinium (alkyl = ethyl, butyl, hexyl, and octyl) bis(trifluoromethansulfonyl)imide (Tf2N) ionic liquids as a function of temperature and excitation wavelength to probe the microheterogeneous nature of these ionic liquids, which are recently reported to be more structured than the imidazolium ionic liquids (Khara and Samanta, J. Phys. Chem. B2012, 116, 13430-13438). Analysis of the measured rotational time constants of the solutes in terms of the Stokes-Einstein-Debye (SED) hydrodynamic theory reveals that with increase in the alkyl chain length attached to the cationic component of the ionic liquids, AP shows stick to superstick behavior, PRODAN rotation lies between stick and slip boundary conditions, whereas anthracene exhibits slip to sub slip behavior. The contrasting rotational dynamics of these probe molecules is a reflection of their location in distinct environments of the ionic liquids thus demonstrating the heterogeneity of these ionic liquids. The microheterogeneity of these media, in particular, those with the long alkyl chain, is further evidence from the excitation wavelength dependence study of the rotational diffusion of the dipolar probe molecules.

  19. Fluoroalkyl and alkyl chains have similar hydrophobicities in binding to the "hydrophobic wall" of carbonic anhydrase.

    Science.gov (United States)

    Mecinović, Jasmin; Snyder, Phillip W; Mirica, Katherine A; Bai, Serena; Mack, Eric T; Kwant, Richard L; Moustakas, Demetri T; Héroux, Annie; Whitesides, George M

    2011-09-07

    The hydrophobic effect, the free-energetically favorable association of nonpolar solutes in water, makes a dominant contribution to binding of many systems of ligands and proteins. The objective of this study was to examine the hydrophobic effect in biomolecular recognition using two chemically different but structurally similar hydrophobic groups, aliphatic hydrocarbons and aliphatic fluorocarbons, and to determine whether the hydrophobicity of the two groups could be distinguished by thermodynamic and biostructural analysis. This paper uses isothermal titration calorimetry (ITC) to examine the thermodynamics of binding of benzenesulfonamides substituted in the para position with alkyl and fluoroalkyl chains (H(2)NSO(2)C(6)H(4)-CONHCH(2)(CX(2))(n)CX(3), n = 0-4, X = H, F) to human carbonic anhydrase II (HCA II). Both alkyl and fluoroalkyl substituents contribute favorably to the enthalpy and the entropy of binding; these contributions increase as the length of chain of the hydrophobic substituent increases. Crystallography of the protein-ligand complexes indicates that the benzenesulfonamide groups of all ligands examined bind with similar geometry, that the tail groups associate with the hydrophobic wall of HCA II (which is made up of the side chains of residues Phe131, Val135, Pro202, and Leu204), and that the structure of the protein is indistinguishable for all but one of the complexes (the longest member of the fluoroalkyl series). Analysis of the thermodynamics of binding as a function of structure is compatible with the hypothesis that hydrophobic binding of both alkyl and fluoroalkyl chains to hydrophobic surface of carbonic anhydrase is due primarily to the release of nonoptimally hydrogen-bonded water molecules that hydrate the binding cavity (including the hydrophobic wall) of HCA II and to the release of water molecules that surround the hydrophobic chain of the ligands. This study defines the balance of enthalpic and entropic contributions to the

  20. Synthesis, nematocidal activity and SAR study of novel difluoromethylpyrazole carboxamide derivatives containing flexible alkyl chain moieties.

    Science.gov (United States)

    Liu, Xing-Hai; Zhao, Wen; Shen, Zhong-Hua; Xing, Jia-Hua; Xu, Tian-Ming; Peng, Wei-Li

    2017-01-05

    A series of novel difluoromethylpyrazole carboxamides derivatives were synthesized by introduction of flexible alkyl chain. Nematicidal bioassay results showed that some of them exhibited good control efficacy against M. incognita, which indicated that these difluoromethylpyrazole carboxamides derivatives might be potential novel lead compounds for discovery new nematicides. The nematicidal activity was affected by the substituted position in the molecule, especially the substitution group on the alkyl chain. It was found that the compound 6-9 and 6-23 possess about 50% inhibition effect against M. incognita even at 5.0 and 1.0 mg L(-1). Meanwhile, greenhouse field trial showed the nematicidal activity of compound 6-9 is a litter weaker than that of Abamectin. The mammalian toxicology results indicated that compound 6-9 was a low-toxicity and low-sensitive compound. In conclusion compound 6-9 is a potential candidate for further development. In addition, the molecular docking simulations revealed that compounds 6 with a flexible NHCOO show its binding affinities for the acetylcholine receptor (AChR), which may provide useful information for further design novel nematicides.

  1. Electrokinetic investigation of surfactant adsorption.

    Science.gov (United States)

    Bellmann, C; Synytska, A; Caspari, A; Drechsler, A; Grundke, K

    2007-05-15

    Fuerstenau [D.W. Fuerstenau, in: M.L. Hair (Ed.), Dekker, New York, 1971, p. 143] has already discussed the role of hydrocarbon chain of surfactants, the effect of alkyl chain length, chain structure and the pH of the solution on the adsorption process of surfactants. Later Kosmulski [M. Kosmulski, Chemical Properties of Material Surfaces, Surfactant Science Series, vol. 102, Dekker, New York, Basel, 2001] included the effect of surfactant concentration, equilibration time, temperature and electrolyte in his approaches. Certainly, the character of the head groups of the surfactant and the properties of the adsorbent surface are the basis for the adsorption process. Different surfactants and adsorbents cause different adsorption mechanisms described firstly by Rosen [M.J. Rosen, Surfactants and Interfacial Phenomena, second ed., Wiley, New York, 1989]. These adsorption mechanisms and their influencing factors were studied by electrokinetic investigations. Here only changes of the charges at the surfaces could be detected. To control the results of electrokinetic investigations they were compared with results from ellipsometric measurements. In the case of surfactant adsorption the chain length was vitally important. It could be shown by the adsorption of alkyl trimethyl ammonium bromides onto polymer films spin coated at wafer surfaces. The influence of the chain length depending on surface properties of the polymer film was studied. Streaming potential measurements were applied for these investigations. The obtained results enabled us to calculate the molar cohesive free energy per mol of CH2-group in the alkaline chain of the surfactant if all other specific adsorption effects were neglected.

  2. Di-Peptide-Modified Gemini Surfactants as Gene Delivery Vectors: Exploring the Role of the Alkyl Tail in Their Physicochemical Behavior and Biological Activity.

    Science.gov (United States)

    Al-Dulaymi, Mays A; Chitanda, Jackson M; Mohammed-Saeid, Waleed; Araghi, Hessamaddin Younesi; Verrall, Ronald E; Grochulski, Pawel; Badea, Ildiko

    2016-09-01

    The aim of this work was to elucidate the structure-activity relationship of new peptide-modified gemini surfactant-based carriers. Glycyl-lysine modified gemini surfactants that differ in the length and degree of unsaturation of their alkyl tail were used to engineer DNA nano-assemblies. To probe the optimal nitrogen to phosphate (N/P) ratio in the presence of helper lipid, in vitro gene expression and cell toxicity measurements were carried out. Characterization of the nano-assemblies was accomplished by measuring the particle size and surface charge. Morphological characteristics and lipid organization were studied by small angle X-ray scattering technique. Lipid monolayers were studied using a Langmuir-Blodgett trough. The highest activity of glycyl-lysine modified gemini surfactants was observed with the 16-carbon tail compound at 2.5 N/P ratio, showing a 5- to 10-fold increase in the level of reporter protein compared to the 12 and 18:1 carbon tail compounds. This ratio is significantly lower compared to the previously studied gemini surfactants with alkyl or amino- spacers. In addition, the 16-carbon tail compound exhibited the highest cell viability (85%). This high efficiency is attributed to the lowest critical micelle concentration of the 16-tail gemini surfactant and a balanced packing of the nanoparticles by mixing a saturated and unsaturated lipid together. At the optimal N/P ratio, all nanoparticles exhibited an inverted hexagonal lipid assembly. The results show that the length and nature of the tail of the gemini surfactants play an important role in determining the transgene efficiency of the delivery system. We demonstrated here that the interplay between the headgroup and the nature of tail is specific to each series, thus in the process of rational design, the contribution of the latter should be assessed in the appropriate context.

  3. The Retention Behaviors of Benzene and Its Alkyl Homologues in Microemulsion Electrokinetic Chromatography

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    The retention behaviors of benzene and its alkyl homologues in microemulsion electrokinetic chromatography were investigated in both anionic and cationic surfactant MEEKC systems. The effects of the composition of microemulsion on retention time and selectivity were studied. A good linear relationship was obtained between log k' and the carbon number of alkyl chain.

  4. Adsorption of quinolone antibiotics in spherical mesoporous silica: Effects of the retained template and its alkyl chain length.

    Science.gov (United States)

    Liang, Zhijie; Zhaob, Zhiwei; Sun, Tianyi; Shi, Wenxin; Cui, Fuyi

    2016-03-15

    In this study, mesoporous silica (meso-silica) MCM-41 and those with the templates retained were synthesized and characterized. Adsorption capacities of the synthesized materials towards typical quinolone antibiotic pollutants, enrofloxacin and norfloxacin as representative, were investigated, and effects of the alkyl chain length of the templates on the adsorption capacity were evaluated. The results of this study indicated that the retained templates enhanced the adsorption capacities (Qmax) of the meso-silica MCM-41 toward hydrophobic enrofloxacin, but had an inhibitory effect on that towards hydrophilic norfloxacin, which were attributed to the hydrophobic inter-environment created by the long alkyl chains of the retained templates. Importantly, the adsorption capacity increased with the increase of the alkyl chain length of the retained templates. Copyright © 2015 Elsevier B.V. All rights reserved.

  5. Polymer gels with associating side chains and their interaction with surfactants

    Science.gov (United States)

    Gordievskaya, Yulia D.; Rumyantsev, Artem M.; Kramarenko, Elena Yu.

    2016-05-01

    Conformational behaviour of hydrophobically modified (HM) polymer gels in solutions of nonionic surfactants is studied theoretically. A HM gel contains hydrophobic side chains (stickers) grafted to its subchains. Hydrophobic stickers are capable to aggregate into joint micelles with surfactant molecules. Micelles containing more than one sticker serve as additional physical cross-links of the network, and their formation causes gel shrinking. In the proposed theoretical model, the interior of the gel/surfactant complex is treated as an array of densely packed spherical polymer brushes consisting of gel subchains tethered to the surface of the spherical sticker/surfactant micelles. Effect of stickers length and grafting density, surfactant concentration and hydrophobicity on gel swelling as well as on hydrophobic association inside it is analyzed. It is shown that increasing surfactant concentration can result in a gel collapse, which is caused by surfactant-induced hydrophobic aggregation of stickers, and a successive gel reswelling. The latter should be attributed to a growing fraction of surfactants in joint aggregates and, hence, increasing number of micelles containing only one sticker and not participating in gel physical cross-linking. In polyelectrolyte (PE) gels hydrophobic aggregation is opposed by osmotic pressure of mobile counterions, so that at some critical ionization degree hydrophobic association is completely suppressed. Hydrophobic modification of polymers is shown to open new ways for controlling gel responsiveness. In particular, it is discussed that incorporation of photosensitive groups into gel subchains and/or surfactant tail could give a possibility to vary the gel volume by light. Since hydrophobic aggregation regularities in gels and solutions are common, we hope our findings will be useful for design of polymer based self-healing materials as well.

  6. Effects of varying surfactant chain lengths on the magnetic, optical and hyperthermia properties of ferrofluids

    Science.gov (United States)

    Rablau, Corneliu; Vaishnava, Prem; Regmi, Rajesh; Sudakar, Chandran; Black, Correy; Lawes, Gavin; Naik, Ratna; Lavoie, Melissa; Kahn, David

    2009-03-01

    We report studies of the structural, magnetic, magneto-thermal and magneto-optic properties of dextran, oleic acid, lauric acid and myristic acid surfacted Fe3O4 nanoparticles of hydrodynamic sizes ranging from 32 nm to 92 nm. All the samples showed saturation magnetization of ˜50 emu/g, significantly smaller than the bulk value for Fe3O4, together with superparamagnetic behavior. The ac magnetization measurements on the dextran coated nanoparticles showed frequency dependent blocking temperature, consistent with superparamgnetic blocking. The ferrofluid heating rates in a 250 Gauss, 100 kHz ac magnetic field varied with the chain lengths of the surfactants, with higher heating rates for longer chains. DC-magnetic-field-induced light scattering patterns produced by two orthogonal He-Ne laser beams passing through the ferrofluid sample revealed different optical signatures for different surfactants.

  7. STRUCTURE AND MORPHOLOGY CHANGES OF HYDROBIOTITES MODIFIED BY CATIONIC SURFACTANTS

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    In this study, X-ray diffraction (XRD), Fourier transform infrared spectrometer (FTIR) together with Scanning probe microscopy (SPM) were used to characterize the structure and morphology of the complexes, where the hydrobiotites (Xinjiang) were modified by single-chain surfactants octyltrimethylammonium bromide (OTMA) and octadecyltrimethylammonium bromide (ODTMA). XRD patterns showed that the structure of complexes was significantly influenced by the surfactant concentration and the alkyl chain length, because obvious changes took place in the basal spacing. Furthermore, according to the XRD results, several arrangements of surfactant molecules within the hydrobiotite interlayer space were deduced. The FTIR spectrum indicated that the surfactant contents in complexes dramatically increased with the alkyl chain length. The SPM micrographs demonstrated that the surfaces of complexes prepared at lower surfactant concentration were relatively flat compared with that prepared at higher concentration, while those with higher surfactant concentration had much steeper surface due to the alkyl chain length. It was concluded that structure and morphology of surfactant/hydrobiotite complexes depend not only on the surfactant concentration, but also strongly on the surfactant species.

  8. Mesitylene-Cored Glucoside Amphiphiles (MGAs) for Membrane Protein Studies: Importance of Alkyl Chain Density in Detergent Efficacy

    DEFF Research Database (Denmark)

    Cho, Kyung Ho; Ribeiro, Orquidea; Du, Yang

    2016-01-01

    are limited in their ability to maintain the structural integrity of membrane proteins and thus there are major efforts underway to develop novel agents with improved properties. We prepared mesitylene-cored glucoside amphiphiles (MGAs) with three alkyl chains and compared these agents with previously...... developed xylene-linked maltoside agents (XMAs) with two alkyl chains and a conventional detergent (DDM). When these agents were evaluated for four membrane proteins including a G protein-coupled receptor (GPCR), some agents such as MGA-C13 and MGA-C14 resulted in markedly enhanced stability of membrane...

  9. A Long-Chain Alkylation of Dialdehyde Starch to Improve Its Thermal Stability and Hydrophobicity

    Directory of Open Access Journals (Sweden)

    Jiang Zhu

    2016-01-01

    Full Text Available Hydrophobic dialdehyde starch (HDAS was synthesized by dialdehyde starch (DAS and eighteen-alkyl primary amine as the raw material in DMSO. The effect of the reaction conditions on the yield of HDAS was investigated such as catalyst content, reaction temperature, reaction time, and the in-feed molar ratio of -CHO/-NH2. Moreover, the optimized test parameters were obtained by conducting orthogonal experiment. The molecular structure and the morphology of HDAS were characterized via Fourier transform infrared spectroscopy (FTIR and scanning electron microscope (SEM. And the thermal stability and the hydrophobic properties of HDAS were investigated by thermal gravimetric analyzer (TG and the hydrophobic testing. The results indicate that the yield of HDAS is the highest up to 44.21%, with feed composition 1 : 0.9, reaction temperature 40°C, reaction time 8 h, and acetic acid content 3%. And the introduction of the long-chain alkyl groups into the DAS backbones will ameliorate efficaciously the thermal stability and the hydrophobic properties of DAS, which almost has no effect on the DAS particle size.

  10. Long-chain acyl-CoA dehydrogenase deficiency as a cause of pulmonary surfactant dysfunction.

    Science.gov (United States)

    Goetzman, Eric S; Alcorn, John F; Bharathi, Sivakama S; Uppala, Radha; McHugh, Kevin J; Kosmider, Beata; Chen, Rimei; Zuo, Yi Y; Beck, Megan E; McKinney, Richard W; Skilling, Helen; Suhrie, Kristen R; Karunanidhi, Anuradha; Yeasted, Renita; Otsubo, Chikara; Ellis, Bryon; Tyurina, Yulia Y; Kagan, Valerian E; Mallampalli, Rama K; Vockley, Jerry

    2014-04-11

    Long-chain acyl-CoA dehydrogenase (LCAD) is a mitochondrial fatty acid oxidation enzyme whose expression in humans is low or absent in organs known to utilize fatty acids for energy such as heart, muscle, and liver. This study demonstrates localization of LCAD to human alveolar type II pneumocytes, which synthesize and secrete pulmonary surfactant. The physiological role of LCAD and the fatty acid oxidation pathway in lung was subsequently studied using LCAD knock-out mice. Lung fatty acid oxidation was reduced in LCAD(-/-) mice. LCAD(-/-) mice demonstrated reduced pulmonary compliance, but histological examination of lung tissue revealed no obvious signs of inflammation or pathology. The changes in lung mechanics were found to be due to pulmonary surfactant dysfunction. Large aggregate surfactant isolated from LCAD(-/-) mouse lavage fluid had significantly reduced phospholipid content as well as alterations in the acyl chain composition of phosphatidylcholine and phosphatidylglycerol. LCAD(-/-) surfactant demonstrated functional abnormalities when subjected to dynamic compression-expansion cycling on a constrained drop surfactometer. Serum albumin, which has been shown to degrade and inactivate pulmonary surfactant, was significantly increased in LCAD(-/-) lavage fluid, suggesting increased epithelial permeability. Finally, we identified two cases of sudden unexplained infant death where no lung LCAD antigen was detectable. Both infants were homozygous for an amino acid changing polymorphism (K333Q). These findings for the first time identify the fatty acid oxidation pathway and LCAD in particular as factors contributing to the pathophysiology of pulmonary disease.

  11. Selective side-chain oxidation of alkyl aromatic compounds catalyzed by cerium modified silver catalysts

    DEFF Research Database (Denmark)

    Beier, Matthias Josef; Schimmoeller, Bjoern; Hansen, Thomas Willum

    2010-01-01

    an elevated pressure was required. Carboxylic acids, such as benzoic acid or p-toluic acid, additionally increased the reaction rate while CeO2 could act both as a promoter and an inhibitor depending on the substrate and the reaction conditions. Silver catalysts were prepared both by standard impregnation......Silver supported on silica effectively catalyzes the aerobic side-chain oxidation of alkyl aromatic compounds under solvent-free conditions. Toluene, p-xylene, ethylbenzene and cumene were investigated as model substrates. Typically, the reaction was performed at ambient pressure; only for toluene...... and flame spray pyrolysis. Addition of a Ce precursor to the FSP catalyst resulted in significantly smaller silver particles. Ce-doped FSP catalysts in general exhibited a superior catalytic performance with TONs up to 2000 except for cumene oxidation that appeared to proceed mainly by homogeneous catalysis...

  12. Effect of fat chain length of sorbitan surfactant on the porosity of mesoporous silica

    Directory of Open Access Journals (Sweden)

    Marco Antonio Utrera Martines

    2009-08-01

    Full Text Available The influence of the fat chain length of sorbitan surfactant was systematically explored, especially its influence on the material pore size. Then, mesoporous silica was synthesized according to a two-step process that provides intermediary stable hybrid micelles using ethoxylated derivative of fatty esters of sorbitan surfactants as the directing-structure agent and tetraethyl orthosilicate Si(OEt4 as the silica source. Finally, the materials’ porosity could be controlled by adjusting the preparation parameters during the two steps synthesis of mesoporous silica.

  13. Partitioning behavior of an acid-cleavable, 1,3-dioxolane alkyl ethoxylate, surfactant in single and binary surfactant mixtures for 2- and 3-phase microemulsion systems according to ethoxylate head group size

    Energy Technology Data Exchange (ETDEWEB)

    Gomez Del Rio, Javier A [ORNL; Hayes, Douglas G [ORNL; Urban, Volker S [ORNL

    2010-01-01

    Partition coefficients for a pH-degradable 1,3-dioxolane alkyl ethoxylate surfactant, 4-CH{sub 3}O (CH{sub 2}CH{sub 2}O){sub 5.6}-CH{sub 2}, 2,2-(CH{sub 2}){sub 12}CH{sub 3}, 2-(CH{sub 2}) CH{sub 3}, 1,3-dioxolane or ''cyclic ketal'' surfactant, CK-2,13-E{sub 5.6,ave}, between isooctane- and water-rich phases of 2- and 3-phase microemulsion systems (K{sub n}) were determined as functions of the ethoxylate size, n, and temperature for the neat surfactant and its binary surfactant mixtures, to understand the partitioning of alkyl ethoxylates possessing a broad distribution of ethoxylate size and to determine conditions required for formation of 3-phase microemulsion systems at an optimal temperature where phase separation occurs rapidly, important for protein purification via proteins selective partitioning to the middle phase, driven by affinity to the second surfactant of the binary mixture. A semi-empirical thermodynamic mathematical model described the partitioning data well, provided optimal temperature values consistent with phase diagrams and theory, and demonstrated that the tail region of CK-2,13-E{sub 5.6,ave} is more polar than the hydrophobes of fatty alcohol ethoxylates. The addition of Aerosol-OT (AOT) removed the temperature sensitivity of CK-2,13-E{sub 5.6,ave}s partitioning, producing 3-phase microemulsion systems between 20 C and 40 C. Analysis of the bottom phases of the 2- and 3-phase microemulsion systems formed by CK-2,13-E{sub 5.6,ave} via small-angle neutron scattering demonstrated the presence of spherical, monodisperse oil-in-water microemulsions.

  14. The polydispersity effect of distributed oxyethylene chains on the cloud points of nonionic surfactants.

    Science.gov (United States)

    Kim, Hui Chan; Kim, Jong-Duk

    2010-12-15

    The cloud points of aqueous solutions containing polyoxyethylene surfactant molecules with a distribution of chain lengths were studied for several nonionic surfactants. Experimentally, the cloud points increased as the oxyethylene chain lengths increased with a linear or logarithmic relation of the number of oxyethylates, as proposed by Schott. An experimental scale, the p-Po scale, was previously developed to correspond to the cloud points, where p is the average number of oxyethylene units per molecule and Po is the shortest chain length reference. However, no previous prediction methods of cloud point addressed systems containing a range of chain lengths. In this work, we propose a rescaling of the representative chain length as s-Po, where s is the cloud point-weighted mean ethylene oxide chain below p, and approximated as (p-Po)/PDI where PDI is the polydispersity index. Using the rescaled length, the experimental data for C(12)Es (lauryl alcohol ethoxylate, LAE), NPE-10 (nonyl phenol ethoxylate) and TDE-10 (tridecyl alcohol ethoxylate) were successfully predicted with no additional parameters, such as {(p-Po)/(PDI)}/CP=a+b{(p-Po)/(PDI)}, where PDI indicates the Broadness of the chain length distribution.

  15. Role of the charge, carbon chain length, and content of surfactant on the skin penetration of meloxicam-loaded liposomes

    Directory of Open Access Journals (Sweden)

    Duangjit S

    2014-04-01

    Full Text Available Sureewan Duangjit,1,2 Boonnada Pamornpathomkul,1 Praneet Opanasopit,1 Theerasak Rojanarata,1 Yasuko Obata,2 Kozo Takayama,2 Tanasait Ngawhirunpat11Faculty of Pharmacy, Silpakorn University, Nakhon Pathom, Thailand; 2Department of Pharmaceutics, Hoshi University, Shinagawa-ku, Tokyo, JapanAbstract: The objective of this study was to investigate the influence of surfactant charge, surfactant carbon chain length, and surfactant content on the physicochemical characteristics (ie, vesicle size, zeta potential, elasticity, and entrapment efficiency, morphology, stability, and in vitro skin permeability of meloxicam (MX-loaded liposome. Moreover, the mechanism for the liposome-enhanced skin permeation of MX was determined by Fourier transform infrared spectroscopy and differential scanning calorimetry. The model formulation used in this study was obtained using a response surface method incorporating multivariate spline interpolation (RSM-S. Liposome formulations with varying surfactant charge (anionic, neutral, and cationic, surfactant carbon chain length (C4, C12, and C16, and surfactant content (10%, 20%, and 29% were prepared. The formulation comprising 29% cationic surfactant with a C16 chain length was found to be the optimal liposome for the transdermal delivery of MX. The skin permeation flux of the optimal formulation was 2.69-fold higher than that of a conventional liposome formulation. Our study revealed that surfactants affected the physicochemical characteristics, stability, and skin permeability of MX-loaded liposomes. These findings provide important fundamental information for the development of liposomes as transdermal drug delivery systems.Keywords: optimal liposome, optimization, transdermal drug delivery, surfactant charge, surfactant carbon chain length, surfactant content

  16. Preparation of nanosize Cu-ZnO/Al{sub 2}O{sub 3} catalyst for methanol synthesis by phase transfer with metal surfactant. 2: Effect of additives and chain length of surfactant

    Energy Technology Data Exchange (ETDEWEB)

    Hu, Z.; Chen, S.; Peng, S. [Chinese Academy of Science, Taiyuan, Shanxi (China). Inst. of Coal Chemistry

    1996-09-25

    Nanosize Cu-ZnO/Al{sub 2}O{sub 3} catalysts for methanol synthesis were prepared by the metal surfactant phase transfer technique. The effects of chain length of surfactant and additives were studied. It was found that the longer the organic chain of surfactant, the more stable the sol particles and the larger the surface area of catalyst. The decomposition temperature of surfactants with longer chains was also higher. For the preparation of Cu-ZnO/Al{sub 2}O{sub 3} catalyst, the surfactant organic chain should not be longer than 11 carbon atoms. A synergist could be used to improve surfactant efficiency. A stabilizing agent was used to strength the stability of sol particles in water. The time needed for oil-water separation was reduced markedly by using a demulsifying agent. The optimal mole ratios of synergist, stabilizing agent, and demulsifying agent to surfactant were, respectively, 0.6, 0.6, and 1.

  17. Desorption of hydrocarbon chains by association with ionic and nonionic surfactants under flow as a mechanism for enhanced oil recovery.

    Science.gov (United States)

    Terrón-Mejía, Ketzasmin A; López-Rendón, Roberto; Goicochea, Armando Gama

    2017-08-29

    The need to extract oil from wells where it is embedded on the surfaces of rocks has led to the development of new and improved enhanced oil recovery techniques. One of those is the injection of surfactants with water vapor, which promotes desorption of oil that can then be extracted using pumps, as the surfactants encapsulate the oil in foams. However, the mechanisms that lead to the optimal desorption of oil and the best type of surfactants to carry out desorption are not well known yet, which warrants the need to carry out basic research on this topic. In this work, we report non equilibrium dissipative particle dynamics simulations of model surfactants and oil molecules adsorbed on surfaces, with the purpose of studying the efficiency of the surfactants to desorb hydrocarbon chains, that are found adsorbed over flat surfaces. The model surfactants studied correspond to nonionic and cationic surfactants, and the hydrocarbon desorption is studied as a function of surfactant concentration under increasing Poiseuille flow. We obtain various hydrocarbon desorption isotherms for every model of surfactant proposed, under flow. Nonionic surfactants are found to be the most effective to desorb oil and the mechanisms that lead to this phenomenon are presented and discussed.

  18. Influence of alkyl chain length on the surface activity of antibacterial polymers derived from ROMP.

    Science.gov (United States)

    Altay, Esra; Yapaöz, Melda Altıkatoğlu; Keskin, Bahadır; Yucesan, Gundoğ; Eren, Tarik

    2015-03-01

    The purpose of this study is to understand the antibacterial properties of cationic polymers on solid surfaces by investigating the structure-activity relationships. The polymer synthesis was carried via ring opening metathesis polymerization (ROMP) of oxanorbornene derivatives. Modulation of molecular weights and alkyl chain lengths of the polymers were studied to investigate the antibacterial properties on the glass surface. Fluorescein (Na salt) staining contact angle measurements were used to characterize the positive charge density and hydrophobicity on the polymer coated surfaces. Positive charge density for the surface coated polymers with molecular weights of 3000 and 10,000 g mol(-1) is observed to be in the range of 2.3-28.5 nmol cm(-2). The ROMP based cationic pyridinium polymer with hexyl unit exhibited the highest bactericidal efficiency against Escherichia coli on solid surface killing 99% of the bacteria in 5 min. However, phenyl and octyl functionalized quaternary pyridinium groups exhibited lower biocidal properties on the solid surfaces compared to their solution phase biocidal properties. Studying the effect of threshold polymer concentrations on the antibacterial properties indicated that changing the concentrations of polymer coatings on the solid surface dramatically influences antibacterial efficiency.

  19. Alkyl Chain Growth on a Transition Metal Center: How Does Iron Compare to Ruthenium and Osmium?

    Directory of Open Access Journals (Sweden)

    Mala A. Sainna

    2015-09-01

    Full Text Available Industrial Fischer-Tropsch processes involve the synthesis of hydrocarbons usually on metal surface catalysts. On the other hand, very few homogeneous catalysts are known to perform a Fischer-Tropsch style of reaction. In recent work, we established the catalytic properties of a diruthenium-platinum carbene complex, [(CpRu2(μ2-H (μ2-NHCH3(μ3-CPtCH3(P(CH332](COn+ with n = 0, 2 and Cp = η5-C5(CH35, and showed it to react efficiently by initial hydrogen atom transfer followed by methyl transfer to form an alkyl chain on the Ru-center. In particular, the catalytic efficiency was shown to increase after the addition of two CO molecules. As such, this system could be viewed as a potential homogeneous Fischer-Tropsch catalyst. Herein, we have engineered the catalytic center of the catalyst and investigated the reactivity of trimetal carbene complexes of the same type using iron, ruthenium and osmium at the central metal scaffold. The work shows that the reactivity should increase from diosmium to diruthenium to diiron; however, a non-linear trend is observed due to multiple factors contributing to the individual barrier heights. We identified all individual components of these reaction steps in detail and established the difference in reactivity of the various complexes.

  20. A chiroptical switch based on supramolecular chirality transfer through alkyl chain entanglement and dynamic covalent bonding.

    Science.gov (United States)

    Lv, Kai; Qin, Long; Wang, Xiufeng; Zhang, Li; Liu, Minghua

    2013-12-14

    Chirality transfer is an interesting phenomenon in Nature, which represents an important step to understand the evolution of chiral bias and the amplification of the chirality. In this paper, we report the chirality transfer via the entanglement of the alkyl chains between chiral gelator molecules and achiral amphiphilic Schiff base. We have found that although an achiral Schiff base amphiphile could not form organogels in any kind of organic solvents, it formed co-organogels when mixed with a chiral gelator molecule. Interestingly, the chirality of the gelator molecules was transferred to the Schiff base chromophore in the mixed co-gels and there was a maximum mixing ratio for the chirality transfer. Furthermore, the supramolecular chirality was also produced based on a dynamic covalent chemistry of an imine formed by the reaction between an aldehyde and an amine. Such a covalent bond of imine was formed reversibly depending on the pH variation. When the covalent bond was formed the chirality transfer occurred, when it was destroyed, the transfer stopped. Thus, a supramolecular chiroptical switch is obtained based on supramolecular chirality transfer and dynamic covalent chemistry.

  1. Nanostructure of mixtures of protic ionic liquids and lithium salts: effect of alkyl chain length.

    Science.gov (United States)

    Méndez-Morales, Trinidad; Carrete, Jesús; Rodríguez, Julio R; Cabeza, Óscar; Gallego, Luis J; Russina, Olga; Varela, Luis M

    2015-02-21

    The bulk structure of mixtures of two protic ionic liquids, propylammonium nitrate and butylammonium nitrate, with a salt with a common anion, is analyzed at room temperature by means of small angle X-ray scattering and classical molecular dynamics simulations. The study of several structural properties, such as density, radial distribution functions, spatial distribution functions, hydrogen bonds, coordination numbers and velocity autocorrelation functions, demonstrates that increasing the alkyl chain length of the alkylammonium cation results in more segregated, better defined polar and apolar domains, the latter having a larger size. This increase, ascribed to the erosion of the H-bond network in the ionic liquid polar regions as salt is added, is confirmed by means of small angle X-ray scattering measurements, which show a clear linear increase of the characteristic spatial sizes of the studied protic ionic liquids with salt concentration, similar to that previously reported for ethylammonium nitrate (J. Phys. Chem. B, 2014, 118, 761-770). In addition, larger ionic liquid cations lead to a lower degree of hydrogen bonding and to more sparsely packed three-dimensional structures, which are more easily perturbed by the addition of lithium salts.

  2. Imidiazolium based ionic liquids: effects of different anions and alkyl chains lengths on the barley seedlings.

    Science.gov (United States)

    Cvjetko Bubalo, Marina; Hanousek, Karla; Radošević, Kristina; Gaurina Srček, Višnja; Jakovljević, Tamara; Radojčić Redovniković, Ivana

    2014-03-01

    We studied the effects of five imidiazolium based ionic liquids with different anions and length of alkyl chains linked to imidazolium ring on the early development of barley (Hordeum vulgare). The inhibitory effect depends on the ionic liquids concentration and chemical structure, whereby the most toxic one was [C10mim][Br], followed by [C7mim][Br], [C4mim][Br], [C4mim][CH3CO2] and [C4mim][BF4]. Both anion and cation structures affected the toxicity of ionic liquid indicating that selection of more biocompatible anions such as [CH3CO2] does not necessarily indicate lower toxicity. Alternation in the extent of oxidative stress and antioxidant enzymes activities were found in barley plants due to ionic liquid treatments. When seedlings were exposed to higher concentrations of ionic liquids, antioxidant system could not effectively remove reactive oxidative species, leading to lipid peroxidation and damage of the photosynthetic system. However, overall data indicated that the performance of barley seedling was improved when all measured enzymes involved in scavenging of reactive oxygen species (ROS) were increased with special emphasis on GPX activities. Since there are no studies about ionic liquid (IL) toxicity in plants, that simultaneously evaluates the antioxidative enzyme system in response to different ILs, this work is valuable for gaining knowledge about the protection mechanism of plants from oxidative stress caused by IL exposure.

  3. N-长链胆酸酰胺的合成%Synthesis of N-long-chain alkyl cholic amide

    Institute of Scientific and Technical Information of China (English)

    王立中; 卞小琴; 周兰香; 李双双; 李广州; 王存德

    2012-01-01

    本文研究了具有长脂链胆酸基非离子型表面活性剂的合成,以商品化胆酸和一系列的长链伯胺(C12~C18)为原料,经过多步反应获得了N-长链烷基胆酸酰胺.目标化合物结构经IR,1H-NMR,13C-NMR,LC-MS等表征确证,同时,对其表面活性进行了初步研究.%The long-chain alkyl cholic amide derivatives were synthesized using bile acid and long-chain alkyl amines as starting materials. All these structures were confirmed by IR/H-NMR^C-NMR.LC-MS and their tensionmetric property was tested. The results were indicated that the long-chain alkyl induced in the cholic acid increased its hydrophobic property.

  4. Effects of tethering alkyl chains for amphiphilic ruthenium complex dyes on their adsorption to titanium oxide and photovoltaic properties.

    Science.gov (United States)

    Ni, Jen-Shyang; Hung, Chun-Yi; Liu, Ken-Yen; Chang, Yu-Hsun; Ho, Kuo-Chuan; Lin, King-Fu

    2012-11-15

    Ruthenium (II) complex dye, Ru(4,4'-dicarboxyl-2,2'-bipyridine)(4-nonyl-2,2'-bipyridine) (NCS)(2), (denoted as RuC9) tethering single alkyl chain was synthesized and well characterized. Its adsorption behavior onto the mesoporous TiO(2) and photovoltaic properties were compared with Z907 which has similar chemical structure but tethers two alkyl chains. RuC9 dyes tend to aggregate into vesicles in the acetonitrile/t-butanol co-solvent as a result of the amphiphilic structure, whereas Z907 dyes aggregate into lamellae. The dye-sensitized solar cell (DSSC) with RuC9 dye showed higher short-circuit photocurrent than that with Z907, attributing to its higher molar optical extinction coefficient and more adsorption amount onto the mesoporous TiO(2). However, the DSSC with Z907 dye has higher open-circuit photovoltage and power conversion efficiency, presumably due to the fact that Z907 with more alkyl chains formed a molecular layer with higher hydrophobicity. It reduced the charge recombination in the interface between the dye-sensitized mesoporous TiO(2) and electrolyte as verified by the electrochemical impedance spectroscopy and intensity modulated photocurrent and photovoltage spectroscopies.

  5. Systematic investigation of zinc aminoalkylphosphonates: influence of the alkyl chain lengths on the structure formation.

    Science.gov (United States)

    Schmidt, Corinna; Stock, Norbert

    2012-03-05

    With the high-throughput (HT) methodology, the bifunctional aminoalkylphosphonic acids (AAPA) linker molecules 2-aminoethyl- (AEPA), 3-aminopropyl- (APPA), and 4-aminobutylphosphonic acid (ABPA) [HO(3)P-C(n)H(2n)-NH(2) (n = 2-4)] and zinc nitrate were used to synthesize new metal phosphonates in order to investigate the influence of the alkyl chain length on the structure formation. The systematic investigations led to one known (ZnO(3)PC(2)H(4)NH(2)) and six new compounds: one using AEPA, three using APPA, and two using ABPA. The crystal structures of five compounds were determined by single crystal X-ray diffraction, using X-ray powder diffraction (XRPD) data as well as structure modeling employing force field methods. For compound 1, Zn(O(3)P-C(2)H(4)-NH(3))(NO(3))(H(2)O) (monoclinic, Cc, a = 4.799(1) Å, b = 29.342(6) Å, c = 5.631(1) Å, β = 91.59(3)°, V = 792.7(3) Å(3), Z = 4), and compound 2, Zn(2)(OH)(O(3)P-C(3)H(6)-NH(3))(NO(3)) (monoclinic, P2/c, a = 12.158(2) Å, b = 5.0315(10) Å, c = 13.952(3) Å, β = 113.23(3)°, V = 784.3(3) Å(3), Z = 2), the structures were determined using single crystal X-ray diffraction data. The crystal structures of [Zn(O(3)P-C(3)H(6)-NH(2))]·H(2)O (3) (monoclinic, P2(1)/c, a = 9.094(2) Å, b = 5.0118(7) Å, c = 16.067(4) Å, β = 90.38(2)°, V = 732.3(2) Å(3), Z = 4) and Zn(O(3)P-C(4)H(8)-NH(2)) (5) (monoclinic, P2(1)/c, a = 8.570(7) Å, b = 8.378(4) Å, c = 9.902(6) Å, β = 90.94(5)°, V = 710.9(8) Å(3), Z = 4) were determined using XRPD data. The structural model for compound 6, Zn(O(3)P-C(4)H(8)-NH(3))(NO(3))(H(2)O), was established using lattice parameters from XRPD data and following crystal structure modeling employing force field methods. The structures depend strongly on the alkyl chain length n. For n = 2 and 4 isoreticular compounds are observed, while n = 3 leads to new structures. Larger amounts of all compounds were obtained employing scale-up syntheses in a conventional oven as well as in a microwave

  6. Molecular pop-up toy: a molecular machine based on folding/unfolding motion of alkyl chains bound to a host.

    Science.gov (United States)

    Ko, Young Ho; Hwang, Ilha; Kim, Hyunuk; Kim, Youngkook; Kim, Kimoon

    2015-01-01

    We have designed and synthesized a new type of molecular machine based on the folding/unfolding motion of an alkyl chain bound to a host, triggered by a redox stimulus. A guest molecule containing a viologen unit with a long alkyl chain 1(2+) and its one-electron reduced species 1 + . form very stable 1:1 host-guest complexes 2(2+) and 2 + ., respectively, with cucurbit[8]uril (CB[8]), where the long alkyl chain of the guests is in a folded conformation inside the host cavity. Upon addition of 2,6-dihydroxynaphthalene as an electron donor, the binary complex 2(2+) turns into a ternary complex 3(2+) through host-stabilized charge-transfer complex formation with the alkyl chain extended into the solution outside the host cavity. The ternary complex behaves like a molecular machine reminiscent of a pop-up toy, as it shows reversible folding/unfolding motion of the alkyl chain of the guest in response to a redox stimulus. For example, one-electron reduction of 3(2+) results in the rapid generation of the 2 + . complex, accompanied by a dramatic conformational change of the alkyl chain from an extended to a folded conformation, and the process can be reversed by oxidation.

  7. Metabolic engineering of Saccharomyces cerevisiae for production of fatty acid short- and branched-chain alkyl esters biodiesel.

    Science.gov (United States)

    Teo, Wei Suong; Ling, Hua; Yu, Ai-Qun; Chang, Matthew Wook

    2015-01-01

    Biodiesel is a mixture of fatty acid short-chain alkyl esters of different fatty acid carbon chain lengths. However, while fatty acid methyl or ethyl esters are useful biodiesel produced commercially, fatty acid esters with branched-chain alcohol moieties have superior fuel properties. Crucially, this includes improved cold flow characteristics, as one of the major problems associated with biodiesel use is poor low-temperature flow properties. Hence, microbial production as a renewable, nontoxic and scalable method to produce fatty acid esters with branched-chain alcohol moieties from biomass is critical. We engineered Saccharomyces cerevisiae to produce fatty acid short- and branched-chain alkyl esters, including ethyl, isobutyl, isoamyl and active amyl esters using endogenously synthesized fatty acids and alcohols. Two wax ester synthase genes (ws2 and Maqu_0168 from Marinobacter sp.) were cloned and expressed. Both enzymes were found to catalyze the formation of fatty acid esters, with different alcohol preferences. To boost the ability of S. cerevisiae to produce the aforementioned esters, negative regulators of the INO1 gene in phospholipid metabolism, Rpd3 and Opi1, were deleted to increase flux towards fatty acyl-CoAs. In addition, five isobutanol pathway enzymes (Ilv2, Ilv5, Ilv3, Aro10, and Adh7) targeted into the mitochondria were overexpressed to enhance production of alcohol precursors. By combining these engineering strategies with high-cell-density fermentation, over 230 mg/L fatty acid short- and branched-chain alkyl esters were produced, which is the highest titer reported in yeast to date. In this work, we engineered the metabolism of S. cerevisiae to produce biodiesels in the form of fatty acid short- and branched-chain alkyl esters, including ethyl, isobutyl, isoamyl and active amyl esters. To our knowledge, this is the first report of the production of fatty acid isobutyl and active amyl esters in S. cerevisiae. Our findings will be useful for

  8. Alkyl chain length impacts the antioxidative effect of lipophilized ferulic acid in fish oil enriched milk

    DEFF Research Database (Denmark)

    Sørensen, Ann-Dorit Moltke; Lyneborg, Karina Sieron; Villeneuve, Pierre

    2015-01-01

    Lipophilization of phenolics by esterification with fatty alcohols may alter their localization in an emulsion and thereby their antioxidant efficacy. In this study, synthesized unbranched alkyl ferulates were evaluated as antioxidants in fish oil enriched milk. Lipid oxidation was determined...

  9. Organomontmorillonites Modified with 2-Methacryloyloxy Ethyl Alkyl Dimethyl Ammonium Bromide

    Institute of Scientific and Technical Information of China (English)

    WANG Jian-quan; WU Wen-hui

    2007-01-01

    Organomontmorillonites (organo-MMT) were synthesized by means of montmorillonites (MMT) modified with a series of 2-methacryloyloxy ethyl alkyl dimethyl ammonium bromide (MAAB) having different alkyl chain lengths as cationic surfactants through a cationic exchanging reaction, and were characterized by FTIR, TG, elemental analysis, and XRD. The microenvironment of the organic interlayer such as the orientation and arrangement of the alkyl chains of MAAB, as well as the properties of nanocomposite hydrogels, were also investigated. The amount of organic components absorbed on interlayer and the basal spacing of organo-MMT both increase with the increasing of alkyl length of MAAB. When carbon number of alkyl chain is in the region of 8 to 14, the alkyl chains between layers would adopt a disordered gauche conformation; while the carbon number is 16, an ordered all-trans conformation with a vertical orientation would be found together with the disordered gauche conformation according to the results of XRD and FTIR. Due to the difference of microenvironment of organic interlayer, the Young's moduli of the nanocomposite hydrogels increased as the alkyl chains of MAAB became longer.

  10. Structure-activity relationships of alkylxanthines: alkyl chain elongation at the N1- or N7-position decreases cardiotonic activity in the isolated guinea pig heart.

    Science.gov (United States)

    Sanae, F; Ohmae, S; Kurita, M; Sawanishi, H; Takagi, K; Miyamoto, K

    1995-10-01

    Relationships between the alkyl substitutions (C1-C6) and cardiac inotropic activities of xanthine derivatives were studied in isolated guinea pig heart muscles. Most of the alkylxanthines exhibited positive inotropic activity on the left atrium, which was increased with an elongation of alkyl chain at the N3-position but decreased by substitution of a long alkyl group at the N1- or N7-position of the xanthine skeleton. Although positive inotropic activity in the right ventricular papillary muscle was also increased by longer alkyl groups at the N3-position, the inotropic activity became negative with an increment in alkyl chain length at the N1- or N7-position. The positive inotropic activity of alkylxanthines was correlated with their inhibitory activity on the phosphodiesterase (PDE) III isoenzyme. Adenosine A1 antagonism and PDE IV inhibitory activity were also partly associated with the inotropic activity because H-89, an inhibitor of cyclic AMP-dependent protein kinase, diminished the positive inotropic action and potentiated the negative inotropic action. These results indicate that the positive inotropic activity of alkylxanthines becomes weak with elongation of alkyl chains at the N1- and N7-positions; In particular, xanthines having two long alkyl chains show a negative inotropic activity on the right ventricular papillary muscle, an effect that could not be elucidated from their cyclic AMP-dependent action.

  11. The effect of alkyl chain length on the level of capping of silicon nanoparticles produced by a one-pot synthesis route based on the chemical reduction of micelle

    Science.gov (United States)

    Ashby, Shane P.; Thomas, Jason A.; Coxon, Paul R.; Bilton, Matthew; Brydson, Rik; Pennycook, Timothy J.; Chao, Yimin

    2013-02-01

    Silicon nanoparticles (SiNPs) can be synthesized by a variety of methods. In many cases these routines are non-scalable with low product yields or employ toxic reagents. One way to overcome these drawbacks is to use one-pot synthesis based on the chemical reduction of micelles. In the following study trichloroalkylsilanes of differing chain lengths were used as a surfactant, and the level of capping, surface bonding and size of the nanoparticles formed has been investigated. FTIR results show that the degree of alkyl capping for SiNPs with different capping layers was constant, although SiNPs bound with shorter chains display a much higher level of Si-O owing to the reaction of the ethanol used in the method with uncapped sites on the particle. SiNPs with longer chain length capping show a sharp Si-H peak on the FTIR, these were heated at reflux with the corresponding 1-alkene to fully cap these particles, resulting in a reduction/disappearance of this peak with a minimal change in the intensity of the Si-O peak. Other techniques used to analyze the surface bonding and composition, XPS, 1H-NMR, and TEM/EDX, show that alkyl-capped SiNPs have been produced using this method. The optical properties showed no significant changes between the different capped SiNPs.

  12. Polymer-grafted lignin surfactants prepared via reversible addition-fragmentation chain-transfer polymerization.

    Science.gov (United States)

    Gupta, Chetali; Washburn, Newell R

    2014-08-12

    Kraft lignin grafted with hydrophilic polymers has been prepared using reversible addition-fragmentation chain-transfer (RAFT) polymerization and investigated for use as a surfactant. In this preliminary study, polyacrylamide and poly(acrylic acid) were grafted from a lignin RAFT macroinitiator at average initiator site densities estimated to be 2 per particle and 17 per particle. The target degrees of polymerization were 50 and 100, but analysis of cleaved polyacrylamide was consistent with a higher average molecular weight, suggesting not all sites were able to participate in the polymerization. All materials were readily soluble in water, and dynamic light scattering data indicate polymer-grafted lignin coexisted in isolated and aggregated forms in aqueous media. The characteristic size was 15-20 nm at low concentrations, and aggregation appeared to be a stronger function of degree of polymerization than graft density. These species were surface active, reducing the surface tension to as low as 60 dyn/cm at 1 mg/mL, and a greater decrease was observed than for polymer-grafted silica nanoparticles, suggesting that the lignin core was also surface active. While these lignin surfactants were soluble in water, they were not soluble in hexanes. Thus, it was unexpected that water-in-oil emulsions formed in all surfactant compositions and solvent ratios tested, with average droplet sizes of 10-20 μm. However, although polymer-grafted lignin has structural features similar to nanoparticles used in Pickering emulsions, its interfacial behavior was qualitatively different. While at air-water interfaces, the hydrophilic grafts promote effective reductions in surface tension, we hypothesize that the low grafting density in these lignin surfactants favors partitioning into the hexanes side of the oil-water interface because collapsed conformations of the polymer grafts improve interfacial coverage and reduce water-hexanes interactions. We propose that polymer-grafted lignin

  13. Production of long chain alkyl esters from carbon dioxide and electricity by a two-stage bacterial process.

    Science.gov (United States)

    Lehtinen, Tapio; Efimova, Elena; Tremblay, Pier-Luc; Santala, Suvi; Zhang, Tian; Santala, Ville

    2017-11-01

    Microbial electrosynthesis (MES) is a promising technology for the reduction of carbon dioxide into value-added multicarbon molecules. In order to broaden the product profile of MES processes, we developed a two-stage process for microbial conversion of carbon dioxide and electricity into long chain alkyl esters. In the first stage, the carbon dioxide is reduced to organic compounds, mainly acetate, in a MES process by Sporomusa ovata. In the second stage, the liquid end-products of the MES process are converted to the final product by a second microorganism, Acinetobacter baylyi in an aerobic bioprocess. In this proof-of-principle study, we demonstrate for the first time the bacterial production of long alkyl esters (wax esters) from carbon dioxide and electricity as the sole sources of carbon and energy. The process holds potential for the efficient production of carbon-neutral chemicals or biofuels. Copyright © 2017 Elsevier Ltd. All rights reserved.

  14. Study of adjuvant effect of model surfactants from the groups of alkyl sulfates, alkylbenzene sulfonates, alcohol ethoxylates and soaps

    DEFF Research Database (Denmark)

    Clausen, S K; Sobhani, S; Poulsen, O M

    2000-01-01

    The sodium salts of representatives of anionic surfactants, dodecylbenzene sulfonate (SDBS), dodecyl sulfate (SDS) and coconut oil fatty acids, and a nonionic surfactant, dodecyl alcohol ethoxylate, were studied for adjuvant effect on the production of specific IgE antibodies in mice...... showed a statistically significant increase in OVA specific IgE levels. After two boosters, a statistically significant suppression in OVA-specific IgE production occurred with SDS (1000 mg/l), SDBS (1000 and 100 mg/l), coconut soap (1000 mg/l) and the alcohol ethoxylate (10 mg/l). This study suggests...

  15. Transesterification reaction between medium- and long-chain fatty acid triglycerides using surfactant-modified lipase.

    Science.gov (United States)

    Mogi, K; Nakajima, M; Mukataka, S

    2000-03-05

    Transesterification between medium-chain fatty acid triglycerides (MCT) and long-chain fatty acid triglycerides (LCT) in a nonsolvent system was investigated using surfactant modified lipase which is a complex of lipase, Rhizopus japonicus and surfactant, sorbitan monostearate. 74% conversion of was obtained after a 48-h reaction period, and the triglyceride composition was well described by the 1, 3-random 2-random stochastic model. The transesterification reaction between MCT and LCT closely followed the simple kinetic model, and the change in MCT and LCT contents could be simulated using one parameter. The effects of the water activity (A(w)) of modified lipase, the water content of the reaction system and the reaction temperature on the reaction rate were studied. A modified lipase A(w) of 0.35 and a water content of the reaction system at 0.09 wt % showed the highest activity. Inactivation did not occur below 60 degrees C, however, the activity decreased at temperatures over 70 degrees C. Copyright 2000 John Wiley & Sons, Inc.

  16. The transfection efficiency of calix[4]arene-based lipids: the role of the alkyl chain length.

    Science.gov (United States)

    Mochizuki, Shinichi; Nishina, Koichi; Fujii, Shota; Sakurai, Kazuo

    2015-02-01

    The size, surface charge, and microstructure of lipoplexes comprising cationic lipids and nucleic acids are important factors for transfection efficiency. As these properties are largely determined by the cationic lipids used, a number of studies on the relationship between cationic lipids and the transfection efficiency have been reported. Among the many cationic lipids, lipids with multivalent cationic head groups are expected to be potent transfection reagents. Here, we prepared calix[4]arene-based lipids with different alkyl chain lengths from C3 to C15 and evaluated the relationship between the alkyl chain length and the transfection efficiency. C6 lipoplexes exhibited the highest transfection efficiency among all lipoplexes. The gene expression with C9 and C12 lipoplexes was slightly lower than that with C6 lipoplexes. C3 lipoplexes hardly induced gene expression, while C15 lipoplexes exhibited no complexation with plasmid DNA. Although all lipoplexes exhibited nearly identical characteristics, they exhibited different behaviours in terms of the interactions between the lipoplexes and anionic micelles comprising phosphatidylserine, a model of endosomal vehicle. After mixing with phosphatidylserine micelles, C6 lipoplexes released the bound plasmid DNA at pH 5 but not at pH 7, indicating that they can interact with the late endosomal membrane after being incorporated into cells. No plasmid DNA was released from C9 or C12 lipoplexes at either pH values. Thus, the alkyl chain length of cationic lipids is related to their interaction with the endosomal compartment and can provide a basis for the design of novel transfection reagents.

  17. Molecular structure of an alkyl-side-chain polymer-water interface: origins of contact angle hysteresis.

    Science.gov (United States)

    Rangwalla, Hasnain; Schwab, Alexander D; Yurdumakan, Betül; Yablon, Dalia G; Yeganeh, Mohsen S; Dhinojwala, Ali

    2004-09-28

    A new and direct approach to verify surface heterogeneity as the microscopic origin of contact-angle hysteresis is demonstrated. IR-visible sum-frequency-generation spectroscopy (SFG) was used to selectively probe the molecules at the interface of an alkyl-side-chain polymer [poly(vinyl n-octadecyl carbamate-co-vinyl acetate)] with water. The spectra indicate that in contact with water, the polymer surface is heterogeneous (having areas of differing surface energies). This evidence of surface heterogeneity supports the hysteresis observed in the advancing and receding contact angles of the polymer surface with water. The same measurements made for the chemically and structurally similar surface of an octadecyltrichlorosilane self-assembled monolayer indicates a homogeneous surface at the water interface. In this case, contact-angle hysteresis measurements implicate surface roughness as the cause of hysteresis. Atomic force microscopy measurements of roughness for these surfaces further support our conclusions. The polymer-water interface was probed using SFG at above-ambient temperatures, and an order-to-disorder transition (ODT) of alkyl side chains at the interface was observed, which closely follows the melting of crystalline side chains in the bulk. This transition explains the increased wettability of the polymer, by water, when the temperature is raised above the bulk melting temperature. Furthermore, the irreversibility of this ODT suggests that the disordered polymer-water interface is the thermodynamic equilibrium state, whereas the before-heating structure of this interface is a kinetically hindered metastable state.

  18. A coacervative extraction based on single-chain and double-chain cationic surfactants.

    Science.gov (United States)

    Kukusamude, Chunyapuk; Quirino, Joselito P; Srijaranai, Supalax

    2016-11-11

    A coacervative extraction (CAE) with the common cationic surfactants dodecyltrimethylammonium bromide (DTAB) and didodecyldimethylammonium bromide (DDAB) was firstly developed. Notable characteristics of the CAE was the use of low concentration of salt (0.1molL(-1) NaBr) at ambient temperature and without the requirement of organic solvent. The CAE was based on phase separation due to the neutralization of the surface charge of the micelle by electrostatic interaction with the predominant common counter ion (bromide). The coacervative phase was subjected to an optimized micellar liquid chromatography with UV (MLC-UV) method without any treatments. The method was applied to the determination of penicillins including amoxicillin, ampicillin, penicillin-G, oxacillin, and cloxacillin in milk samples. Method detection limits (MDLs) from standard were 0.5-2ngmL(-1), and 40-80-fold analyte enrichment were obtained. The CAE-MLC-UV has shown to be of high potential for the analysis of five penicillins in milk with recoveries >90%.

  19. Long Chain Alkyl Esters of Hydroxycinnamic Acids as Promising Anticancer Agents: Selective Induction of Apoptosis in Cancer Cells.

    Science.gov (United States)

    Menezes, José C J M D S; Edraki, Najmeh; Kamat, Shrivallabh P; Khoshneviszadeh, Mahsima; Kayani, Zahra; Mirzaei, Hossein Hadavand; Miri, Ramin; Erfani, Nasrollah; Nejati, Maryam; Cavaleiro, José A S; Silva, Tiago; Saso, Luciano; Borges, Fernanda; Firuzi, Omidreza

    2017-08-23

    Cancer is the major cause of morbidity and mortality worldwide. Hydroxycinnamic acids (HCAs) are naturally occurring compounds and their alkyl esters may possess enhanced biological activities. We evaluated C4, C14, C16, and C18 alkyl esters of p-coumaric, ferulic, sinapic, and caffeic acids (19 compounds) for their cytotoxic activity against four human cancer cells and also examined their effect on cell cycle alteration and apoptosis induction. The tetradecyl (1c) and hexadecyl (1d) esters of p-coumaric acid and tetradecyl ester of caffeic acid (4c), but not the parental HCAs, were selectively effective against MOLT-4 (human lymphoblastic leukemia) cells with IC50 values of 0.123 ± 0.012, 0.301 ± 0.069 and 1.0 ± 0.1 μM, respectively. Compounds 1c, 1d, and 4c significantly increased apoptotic cells in sub-G1 phase and activated the caspase-3 enzyme in MOLT-4 cells. Compound 1c was 15.4 and 23.6 times more potent than doxorubicin and cisplatin, respectively, against the drug resistant MES-SA-DX5 uterine sarcoma cells. These p-coumarate esters were several times less effective against NIH/3T3 fibroblast cells. Docking studies showed that 1c may cause cytotoxicity by interaction with carbonic anhydrase IX. In conclusion, long chain alkyl esters of p-coumaric acid are promising scaffolds for selective apoptosis induction in cancer cells.

  20. Self-Spreading of Lipid Bilayer on a Hydrophobic Surface Made by Self-Assembled Monolayer with Short Alkyl Chain.

    Science.gov (United States)

    Omori, Yuya; Sakaue, Hiroyuki; Takahagi, Takayuki; Suzuki, Hitoshi

    2016-04-01

    Behaviors of self-spreading of lipid bilayer membrane on a glass surface modified with self-assembled monolayer (SAM) with short alkyl chain were observed with fluorescence microscopy. Hydrophobic surface made by SAM was found to hamper the self-spreading phenomenon but the lipid bilayer spread on a hydrophilic one where SAM was decomposed by oxidation. On a binary surface having a hydrophobic region and a hydrophilic one, the lipid bilayer spread on the hydrophilic region but it stopped at the boundary of the hydrophobic region.

  1. Adsorption of dimeric surfactants in lamellar silicates

    Energy Technology Data Exchange (ETDEWEB)

    Balcerzak, Mateusz; Pietralik, Zuzanna [Department of Macromolecular Physics, Faculty of Physics, A. Mickiewicz University, Umultowska 85, 61-614 Poznań (Poland); Domka, Ludwik [Department of Metalorganic Chemistry, Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań (Poland); Skrzypczak, Andrzej [Institute of Chemical Technology, Poznań University of Technology, Berdychowo 4, 60-965 Poznań (Poland); Kozak, Maciej, E-mail: mkozak@amu.edu.pl [Department of Macromolecular Physics, Faculty of Physics, A. Mickiewicz University, Umultowska 85, 61-614 Poznań (Poland)

    2015-12-01

    Highlights: • The intercalation of dimeric surfactants changed the morphology of MMT samples. • XRD indicated structures formed by surfactant molecules in interlayer space. • The four-step thermal decomposition of dimeric surfactant, confirms intercalation. - Abstract: The adsorption of different types of cationic surfactants in lamellar silicates changes their surface character from hydrophilic to hydrophobic. This study was undertaken to obtain lamellar silicates modified by a series of novel dimeric (gemini) surfactants of different length alkyl chains and to characterise these organophilised materials. Synthetic sodium montmorillonite SOMASIF® ME 100 (M) and enriched bentonite of natural origin (Nanoclay – hydrophilic bentonite®) were organophilised with dimeric (gemini) surfactants (1,1′-(1,4-butanediyl)bis(alkoxymethyl)imidazolium dichlorides). As a result of surfactant molecule adsorption in interlamellar space, the d-spacing (d{sub 001}) increased from 0.97 nm (for the anhydrous structure) to 2.04 nm. A Fourier transform infrared spectroscopy (FTIR) analysis of the modified systems reveals bands assigned to the stretching vibrations of the CH{sub 2} and CH{sub 3} groups and the scissoring vibrations of the NH group from the structure of the dimeric surfactants. Thermogravimetric (TG) and derivative thermogravimetric (DTG) studies imply a four-stage process of surfactant decomposition. Scanning electron microscopy (SEM) images provide information on the influence of dimeric surfactant intercalation into the silicate structures. Particles of the modified systems show a tendency toward the formation of irregularly shaped agglomerates.

  2. THE ADSORPTION OF LINEAR POLY(N-ISOPROPYLACRYLAMIDE) CHAINS ON SURFACTANT-FREE POLYSTYRENE NANOPARTICLES

    Institute of Scientific and Technical Information of China (English)

    Jun Gao; Tengjiao Hu; Yubao Zhang; Pei Li; Chi Wu

    1999-01-01

    The adsorption of linear poly(N-isopropylacrylamide) (PNIPAM) chains on surfactant-free polystyrene (PS) nanoparticles was used as a model system to study the hydrophobic adsorption of polymer on the surface, because the hydrophobility of PNIPAM can be continuously varied by a small temperature change. The adsorption was investigated by a combination of static and dynamic laser light scattering (LLS)measurements. In static LLS, the absolute excess scattered light intensity led to the amount of PNIPAM adsorbed on the surface. In dynamic LLS, the hydrodynamic thickness of the adsorbed PNIPAM layer was accurately measured. For a given particle concentration, the adsorption increases as the PNIPAM concentration and the incubation temperature increase. The average density of the adsorbed PNIPAM layer is reciprocally proportional to the number of the PNIPAM chains on the surface, revealing a simple scaling of the chain density distribution. The adsorption follows the Langmuir's isotherm. The enthalpy change estimated from the adsorption at 25℃ and 30℃ is slightly positive, indicating that the adsorption involves the coil-to-globule transition of the chains on the surface.

  3. Fluoroalkyl and Alkyl Chains Have Similar Hydrophobicities in Binding to the “Hydrophobic Wall” of Carbonic Anhydrase

    Energy Technology Data Exchange (ETDEWEB)

    J Mecinovic; P Snyder; K Mirica; S Bai; E Mack; R Kwant; D Moustakas; A Heroux; G Whitesides

    2011-12-31

    The hydrophobic effect, the free-energetically favorable association of nonpolar solutes in water, makes a dominant contribution to binding of many systems of ligands and proteins. The objective of this study was to examine the hydrophobic effect in biomolecular recognition using two chemically different but structurally similar hydrophobic groups, aliphatic hydrocarbons and aliphatic fluorocarbons, and to determine whether the hydrophobicity of the two groups could be distinguished by thermodynamic and biostructural analysis. This paper uses isothermal titration calorimetry (ITC) to examine the thermodynamics of binding of benzenesulfonamides substituted in the para position with alkyl and fluoroalkyl chains (H{sub 2}NSO{sub 2}C{sub 6}H{sub 4}-CONHCH{sub 2}(CX{sub 2}){sub n}CX{sub 3}, n = 0-4, X = H, F) to human carbonic anhydrase II (HCA II). Both alkyl and fluoroalkyl substituents contribute favorably to the enthalpy and the entropy of binding; these contributions increase as the length of chain of the hydrophobic substituent increases. Crystallography of the protein-ligand complexes indicates that the benzenesulfonamide groups of all ligands examined bind with similar geometry, that the tail groups associate with the hydrophobic wall of HCA II (which is made up of the side chains of residues Phe131, Val135, Pro202, and Leu204), and that the structure of the protein is indistinguishable for all but one of the complexes (the longest member of the fluoroalkyl series). Analysis of the thermodynamics of binding as a function of structure is compatible with the hypothesis that hydrophobic binding of both alkyl and fluoroalkyl chains to hydrophobic surface of carbonic anhydrase is due primarily to the release of nonoptimally hydrogen-bonded water molecules that hydrate the binding cavity (including the hydrophobic wall) of HCA II and to the release of water molecules that surround the hydrophobic chain of the ligands. This study defines the balance of enthalpic and

  4. Distinct changes in pulmonary surfactant homeostasis in common beta-chain-and GM-CSF-deficient mice

    NARCIS (Netherlands)

    Reed, JA; Ikegami, M; Robb, L; Begley, CG; Ross, G; Whitsett, JA

    Pulmonary alveolar proteinosis (PAP) is caused by inactivation of either granulocyte-macrophage colony-stimulating factor (GMCSF) or GM receptor common beta-chain (beta(c)) genes in mice [GM(-/-), beta(c)(-/-)], demonstrating a critical role of GM-CSF signaling in surfactant homeostasis. To

  5. Comparative study of the intermolecular dynamics of imidazolium-based ionic liquids with linear and branched alkyl chains: OHD-RIKES measurements.

    Science.gov (United States)

    Xue, Lianjie; Bardak, Fehmi; Tamas, George; Quitevis, Edward L

    2017-02-08

    This article describes a comparative study of the low-frequency (0-450 cm(-1)) Kerr spectra of the branched 1-(iso-alkyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)amide ([(N - 2)mCN-1C1im][NTf2] with N = 3-7) ionic liquids (ILs) and that of the linear 1-(n-alkyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)amide ([CNC1im][NTf2] with N = 2-7) ILs. The spectra were obtained by use of femtosecond optical heterodyne-detected Raman-induced Kerr effect spectroscopy (OHD-RIKES). The intermolecular spectrum of a branched IL is similar to that of a linear IL that is of the same alkyl chain length rather than of the same number of carbon atoms in the alkyl chain. This similarity and the lack of a correlation of the first spectral moments and widths of the intermolecular spectra with chain length is mainly attributed to the increase in the dispersion contribution to the total molar cohesive energy being compensated by stretching of the ionic network due to the increasing size of the nonpolar domains, which is dependent only on the length of the alkyl chain.

  6. [Synthesis of a nano-antibacterial inorganic filler containing a quaternary ammonium salt with long chain alkyl and its effect on dental resin composites].

    Science.gov (United States)

    Junling, Wu; Kaiyun, Zhou; Ting, Zhu; Chuanjian, Zhou

    2014-10-01

    This study aimed to synthesize a novel nano-antibacterial inorganic filler that contains a quaternary ammonium salt with long chain alkyl and to report the antibacterial property of dental resin composites. A novel nano-antibacterial inorganic filler that contains a quaternary ammonium salt with long chain alkyl was synthesized based on previous research. The antibacterial property of the filler was measured. The surface of the novel nano-antibacterial inorganic filler was modified by a coupling agent to achieve a good interfacial bonding between the filler and the resin matrix. Infrared spectrum analysis was carried out. The modified novel nano-antibacterial inorganic fillers were then incorporated into the dental resin matrix. The dispersion of the fillers was observed and compared with those incorporated into Tetric N-Ceram, a commercial resin composite, under a scanning electron microscope. Streptococcus mutans was used in testing the antibacterial property of the dental resin composites. A quaternary ammonium salt with a long chain alkyl was successfully grafted onto the surface of nano-silica particles. The novel nano-antibacterial inorganic filler that contains quaternary ammonium salt with a long chain alkyl showed stronger antibacterial efficacy than the antibacterial inorganic filler that contains quaternary ammonium salt with a short chain alkyl. The modified novel antibacterial inorganic fillers displayed a homogeneous dispersion in the resin composite bulk and combined closely with the resin matrix, similar to the Tetric N-Ceram. The resin composites that contain novel antibacterial inorganic fillers showed stronger antibacterial effect on Streptococcus mutans compared with the control group. The novel nano-antibacterial inorganic filler that contains a quaternary ammonium salt with long chain alkyl showed a strong antibacterial property. It also exhibited good compatibility with the dental resin matrix after undergoing coupling treatment.

  7. Synthesis of low-oxide blue luminescent alkyl-functionalized silicon nanoparticles with no nitrogen containing surfactant

    Energy Technology Data Exchange (ETDEWEB)

    Thomas, Jason A.; Ashby, Shane P.; Huld, Frederik [University of East Anglia, School of Chemistry (United Kingdom); Pennycook, Timothy J. [SuperSTEM Laboratory, STFC Daresbury Campus (United Kingdom); Chao, Yimin, E-mail: y.chao@uea.ac.uk [University of East Anglia, School of Chemistry (United Kingdom)

    2015-05-15

    Of ever growing interest in the fields of physical chemistry and materials science, silicon nanoparticles show a great deal of potential. Methods for their synthesis are, however, often hazardous, expensive or otherwise impractical. In the literature, there is a safe, fast and cheap inverse micelle-based method for the production of alkyl-functionalized blue luminescent silicon nanoparticles, which nonetheless found limitations, due to undesirable Si-alkoxy and remaining Si–H functionalization. In the following work, these problems are addressed, whereby an optimisation of the reaction mechanism encourages more desirable capping, and the introduction of alcohol is replaced by the use of anhydrous copper (II) chloride. The resulting particles, when compared with their predecessors through a myriad of spectroscopic techniques, are shown to have greatly reduced levels of ‘undesirable’ capping, with a much lower surface oxide level; whilst also maintaining long-term air stability, strong photoluminescence and high yields.

  8. Ion Specificity and Micellization of Ionic Surfactants: A Monte Carlo Study

    CERN Document Server

    Santos, Alexandre P dos; Levin, Yan

    2014-01-01

    We develop a simulation method which allows us to calculate the critical micelle concentrations for ionic surfactants in the presence of different salts. The results are in good agreement with the experimental data. The simulations are performed on a simple cubic lattice. The anionic interactions with the alkyl chains are taken into account based on the previously developed theory of the interfacial tensions of hydrophobic interfaces: the kosmotropic anions do not interact with the hydrocarbon tails of ionic surfactants, while chaotropic anions interact with the alkyl chains through a dispersion potential proportional to the anionic polarizability.

  9. Solubility of n-butane and 2-methylpropane (isobutane) in 1-alkyl-3-methylimidazolium-based ionic liquids with linear and branched alkyl side-chains.

    Science.gov (United States)

    Pison, Laure; Shimizu, Karina; Tamas, George; Lopes, José Nuno Canongia; Quitevis, Edward L; Gomes, Margarida F Costa

    2015-11-11

    The solubility of n-butane and 2-methylpropane (isobutane) in three ionic liquids - 1-(2-methylpropyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [(2mC3)C1im][Ntf2], 1-(3-methylbutyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [(3mC4)C1im][Ntf2] and 1-methyl-3-pentylimidazolium bis(trifluoromethylsulfonyl)imide [C5C1im][Ntf2] - has been measured at atmospheric pressure from 303 to 343 K. Isobutane is less soluble than n-butane in all the ionic liquids. Henry's constant values range from 13.8 × 10(5) Pa for n-butane in [C5C1im][Ntf2] at 303 K to 64.5 × 10(5) Pa for isobutane in [(2mC3)C1im][Ntf2] at 343 K. The difference in solubility between the two gases can be explained by a more negative enthalpy of solvation for n-butane. A structural analysis of the pure solvents and of the solutions of the gases, probed by molecular dynamics simulations, could explain the differences found in the systems: (i) the nonpolar domains of the ionic liquids accommodate better the long and more flexible n-butane solute; (ii) the small differences in solubility of each gas in the ionic liquids with the same number of carbon atoms in the alkyl side-chains are explained by the absence of large structural differences in the pure solvents. In all cases, the structural analysis of the four ionic liquids confirms that the studied gases can act as probes of the molecular structure of the ionic liquids, the simulations being always compatible with the experimental solubility data.

  10. Applying Alkyl-Chain Surface Functionalizations in Mesoporous Inorganic Structures: Their Impact on Gas Flow and Selectivity Depending on Temperature.

    Science.gov (United States)

    Besser, Benjamin; Ahmed, Atiq; Baune, Michael; Kroll, Stephen; Thöming, Jorg; Rezwan, Kurosch

    2016-10-12

    Porous inorganic capillary membranes are prepared to serve as model structures for the experimental investigation of the gas transport in functionalized mesopores. The porous structures possess a mean pore diameter of 23 nm which is slightly reduced to 20 nm after immobilizing C16-alkyl chains on the surface. Gas permeation measurements are performed at temperatures ranging from 0 to 80 °C using Ar, N2, and CO2. Nonfunctionalized structures feature a gas transport according to Knudsen diffusion with regard to gas flow and selectivity. After C16-functionalization, the gas flow is reduced by a factor of 10, and the ideal selectivities deviate from the Knudsen theory. CO2 adsorption measurements show a decrease in total amount of adsorbed gas and isosteric heat of adsorption. It is hypothesized that the immobilized C16-chains sterically influence the gas transport behavior without a contribution from adsorption effects. The reduced gas flow derives from an additional surface resistance caused by the C16-chains spacially limiting the adsorption and desorption directions for gas molecules propagating through the structure, resulting in longer diffusion paths. In agreement, the gas flow is found to correlate with the molecular diameter of the gas species (CO2 ideal selectivities with the relation [Formula: see text]. The influence on selectivity increases with increasing temperature which leads to the conclusion that the temperature induced movement of the C16-chains is responsible for the stronger interaction between gas molecules and surface functional groups.

  11. Molecular dynamics simulation of the interfacial structure of [C(n)mim][PF6] adsorbed on a graphite surface: effects of temperature and alkyl chain length.

    Science.gov (United States)

    Dou, Q; Sha, M L; Fu, H Y; Wu, G Z

    2011-05-01

    The structures and diffusion behaviors of a series of ionic liquids [C(n)mim][PF(6)] (n = 1, 4, 8 and 12) on a graphite surface have been investigated by means of molecular dynamics simulation. It was found that three or four ordering layers of ionic liquids were formed near the graphite surface, and this layering structure was stable over the temperature range investigated. At the liquid/vacuum interface, the ionic liquid with a butyl chain had a monolayer ordering surface, while [C(8)mim][PF(6)] and [C(12)mim][PF(6)] exhibited a bilayer ordering with a polar domain sandwiched between two orientational nonpolar domains. More impressively, the simulated results showed that for the ionic liquids with alkyl chains longer than C(4), the adjacent alkyl chains in the whole film tended to be parallel to each other, with the imidazolium rings packed closely together. This indicated that the ionic liquids have a better regulated short-range structure than was previously expected. It was also found that both in the bottom layer and in the bulk region, the diffusion of the alkyl chains was much faster than that of the polar groups. However, as the alkyl chain length increased, the charge delocalization in the cation and the enhanced van der Waals interaction between the nonpolar groups contributed by reducing this difference in the diffusivity of major groups.

  12. Antioxidant activity of alkyl gallates and glycosyl alkyl gallates in fish oil in water emulsions: relevance of their surface active properties and of the type of emulsifier.

    Science.gov (United States)

    González, María J; Medina, Isabel; Maldonado, Olivia S; Lucas, Ricardo; Morales, Juan C

    2015-09-15

    The antioxidant activity of gallic acid and a series of alkyl gallates (C4-C18) and glycosylated alkyl gallates (C4-C18) on fish oil-in-water emulsions was studied. Three types of emulsifiers, lecithin, Tween-20 and sodium dodecyl sulphate (SDS) were tested. A nonlinear behavior of the antioxidant activity of alkyl gallates when increasing alkyl chain length was observed for emulsions prepared with lecithin. Medium-size alkyl gallates (C6-C12) were the best antioxidants. In contrast, for emulsions prepared with Tween-20, the antioxidants seem to follow the polar paradox. Glucosyl alkyl gallates were shown previously to be better surfactants than alkyl gallates. Nevertheless, they exhibited a worse antioxidant capacity than their corresponding alkyl gallates, in emulsions prepared with lecithin or Tween-20, indicating the greater relevance of having three OH groups at the polar head in comparison with having improved surfactant properties but just a di-ortho phenolic structure in the antioxidant. Copyright © 2015 Elsevier Ltd. All rights reserved.

  13. Aquatic Macrophytes Inputs of Middle Chain Length n-alkyl Lipids into Lake Sediments: a Linear Algebra Approach

    Science.gov (United States)

    Gao, L.; Huang, Y.

    2009-12-01

    Quantitatively delineating multiple source inputs is a common but often difficult task in geological and environmental researches. Binary mixing model works well for simple two-component mixing problems when the two end members can be accurately defined. However, real world mixing problems usually involve more than two source components, and each component may have many composite profiles. Therefore, binary model is inadequate to provide an accurate estimate of contribution of all the end member sources. In such cases, linear combination model by solving linear algebra equations will have to be developed. In this study, we demonstrate the application of the linear algebra method to accurately calculate the percentage inputs of leaf waxes from different plant groups to lake sediments of Blood Pond and Rocky Pond in Massachusetts. We systematically sampled 28 species, including 6 tree species, 6 grass species, 7 emergent plants, 4 floating and 3 submerged aquatic plants around Blood Pond as well as 6 sediments samples of different depth. The distributions of these plants leaf waxes (n-alkanes and n-alkanoic acids) show distinctively different patterns, but also significant overlaps. To accurately quantify the percentage source inputs, we develop the 4-end member linear combination model. As we have an equation for each of the total 6 n-alkane compounds we use (C23 alkane ~C33 alkane), a 'least square fitting' is applied to solved the overdetermined linear system. Our results show that 91.7% of the total C23 alkane in sediments is derived from floating and submerged plants. We also applied our approach to Rocky Pond in southeastern Massachusetts and found >92 % of mid chain n-alkyl lipids are contributed by floating and submerged plants. Our results provide critical basis for using D/H ratios of mid-chain n-alkyl lipids (such as behenic acid) in lake sediments for reconstructing lake water D/H ratios.

  14. Synthesis and Antimicrobial Activity of Carboxylate Phosphabetaines Derivatives with Alkyl Chains of Various Lengths

    Directory of Open Access Journals (Sweden)

    Irina V. Galkina

    2013-01-01

    Full Text Available The purpose of the present study was to investigate the antibacterial activity of fifteen novel nanosized alkyl esters of carboxylate phosphabetaine: β-(carboxyalkylethyltriphenylphosphonium bromides 4–8, β-(carboxyalkyl-β-methylethyltriphenylphosphonium bromides 9–13, and β-(carboxyalkyl-α-methylethyltriphenylphosphonium bromides 14–18. The in vitro microbiological activity of the synthesized phosphonium bromides against gram-positive and gram-negative bacteria and the yeast Candida albicans was determined in comparison to standard agents. Microbiological results indicate that the synthesized phosphonium salts 4–18 possess a broad spectrum of activity against the tested microorganisms. Every newly synthesized compound was characterized by elemental analyses, IR, 1H NMR, and 31P NMR spectral studies.

  15. Solution properties and emulsification properties of amino acid-based gemini surfactants derived from cysteine.

    Science.gov (United States)

    Yoshimura, Tomokazu; Sakato, Ayako; Esumi, Kunio

    2013-01-01

    Amino acid-based anionic gemini surfactants (2C(n)diCys, where n represents an alkyl chain with a length of 10, 12, or 14 carbons and "di" and "Cys" indicate adipoyl and cysteine, respectively) were synthesized using the amino acid cysteine. Biodegradability, equilibrium surface tension, and dynamic light scattering were used to characterize the properties of gemini surfactants. Additionally, the effects of alkyl chain length, number of chains, and structure on these properties were evaluated by comparing previously reported gemini surfactants derived from cystine (2C(n)Cys) and monomeric surfactants (C(n)Cys). 2C(n)diCys shows relatively higher biodegradability than does C(n)Cys and previously reported sugar-based gemini surfactants. Both critical micelle concentration (CMC) and surface tension decrease when alkyl chain length is increased from 10 to 12, while a further increase in chain length to 14 results in increased CMC and surface tension. This indicates that long-chain gemini surfactants have a decreased aggregation tendency due to the steric hindrance of the bulky spacer as well as premicelle formation at concentrations below the CMC and are poorly packed at the air/water interface. Formation of micelles (measuring 2 to 5 nm in solution) from 2C(n)diCys shows no dependence on alkyl chain length. Further, shaking the mixtures of aqueous 2C(n)diCys surfactant solutions and squalane results in the formation of oil-in-water type emulsions. The highly stable emulsions are formed using 2C₁₂diCys or 2C₁₄diCys solution and squalane in a 1:1 or 2:1 volume ratio.

  16. Studies on the solvation dynamics of coumarin 153 in 1-ethyl-3-methylimidazolium alkylsulfate ionic liquids: dependence on alkyl chain length.

    Science.gov (United States)

    Das, Sudhir Kumar; Sarkar, Moloy

    2012-08-06

    Steady-state and time-resolved fluorescence behavior of coumarin 153 (C153) is investigated in a series of 1-ethyl-3-methylimidazolium alkylsulfate ([C(2)mim][C(n)OSO(3)]) ionic liquids differing only in the length of the linear alkyl chain (n = 4, 6, and 8) in the anion. The aim of the present study is to understand the role of alkyl chain length in solute rotation and solvation dynamics of C153 in these ionic liquids. The blueshift observed in the steady-state absorption and emission maxima of C153 on going from the C(4)OSO(3) to the C(8)OSO(3) system indicates increasing nonpolar character of the microenvironment of the solute with increasing length of the alkyl side chain of the anion of the ionic liquids. The average solvation time is also found to increase on changing the substituent from butyl to octyl, and this is attributed to the increase in the bulk viscosity of the ILs. A steady blueshift of the time-zero maximum of the fluorescence spectrum with increasing alkyl chain length also indicates that the probe molecule experiences a less polar environment in the early part of the dynamics. Rotational dynamics of C153 are also analyzed by using the Stokes-Einstein-Debye (SED), Gierer-Wirtz (GW), and Dote-Kivelson-Schwartz (DKS) theories. Analyses of the results seem to suggest decoupling of the rotational motion of the probe from solvent viscosity.

  17. Probing the effects of the ester functional group, alkyl side chain length and anions on the bulk nanostructure of ionic liquids: a computational study.

    Science.gov (United States)

    Fakhraee, Mostafa; Gholami, Mohammad Reza

    2016-04-14

    The effects of ester addition on nanostructural properties of biodegradable ILs composed of 1-alkoxycarbonyl-3-alkyl-imidazolium cations ([C1COOCnC1im](+), n = 1, 2, 4) combined with [Br](-), [NO3](-), [BF4](-), [PF6](-), [TfO](-), and [Tf2N](-) were explored by using the molecular dynamics (MD) simulations and quantum theory of atoms in molecules (QTAIM) analysis at 400 K. Various thermodynamic properties of these ILs were extensively computed in our earlier work (Ind. Eng. Chem. Res., 2015, 54, 11678-11700). Nano-scale segregation analysis demonstrates the formation of a small spherical island-like hydrocarbon within the continuous ionic domain for ILs with short alkyl side chain ([C1COOC1C1im]), and a sponge-like nanostructure for the compound with long alkyl side chain ([C1COOC4C1im]). Ester-functionalized ILs with ethyl side chain ([C1COOC2C1im]) are the turning point between two different morphologies. Non-polar channels were observed for [C1COOC4C1im] ILs composed of smaller anions such as [Br] and [NO3], whereas clustering organization was found for the other anions. Formation of the spherical micelle-like nanostructure was seen for lengthened cations. Finally, the incorporation of an ester group into the alkyl side chain of the cation leads to stronger segregation between charged and uncharged networks, which consequently increased the possibility of self-assembly and micelle formation.

  18. Fabrication and tribological properties of self-assembled monolayer of n-alkyltrimethoxysilane on silicon: Effect of SAM alkyl chain length

    Science.gov (United States)

    Huo, Lixia; Du, Pengcheng; Zhou, Hui; Zhang, Kaifeng; Liu, Peng

    2017-02-01

    It is well known that the self-assembled organic molecules on a solid surface exhibit the friction-reducing performance. However, the effect of the molecular size of the self-assembled organic molecules has not been established. In the present work, self-assembled monolayers (SAMs) of n-alkyltrimethoxysilanes with different alkyl chain lengths (C6, C12, or C18) were fabricated on silicon substrate. The water contact angles of the SAMs increased from 26.8° of the hydroxylated silicon substrate to near 60° after self-assembly. The atomic force microscopy (AFM) analysis results showed that the mean roughness (Ra) of the SAMs decreased with increasing the alkyl chain length. The tribological properties of the SAMs sliding against Al2O3 ball were evaluated on an UMT-2 tribometer, and the worn surfaces of the samples were analyzed by means of Nano Scratch Tester and surface profilometry. It was found that lowest friction coefficient and smallest width of wear were achieved with the SAMs of C12 alkyl chain (C12-SAM). The superior friction reduction and wear resistance of the SAMs in comparison with the bare silicon substrate are attributed to good adhesion of the self-assembled films to the substrate, especially the C12-SAM with desirable alkyl chain length.

  19. Synthesis and antibacterial activity of sulfonamide derivatives at C-8 alkyl chain of anacardic acid mixture isolated from a natural product cashew nut shell liquid (CNSL)

    Indian Academy of Sciences (India)

    N Subhakara Reddy; A Srinivas Rao; M Adharvana Chari; V Ravi Kumar; V Jyothy; V Himabindu

    2012-05-01

    Synthesis and antibacterial activity of some novel biologically active sulfonamide derivatives at C-8 alkyl chain of anacardic acid (7a-7l), prepared from commercially available anacardic acid mixture (1a-d). These compounds were tested for Gram positive and Gram negative bacterial cultures; most of the compounds showed higher antibacterial activity compared with standard drug ampicillin.

  20. Solubilisation of different medium chain esters in zwitterionic surfactant solutions--effects on phase behaviour and structure.

    Science.gov (United States)

    Barth, A; Prévost, S; Popig, J; Dzionara, M; Hedicke, G; Gradzielski, M

    2011-12-01

    We studied the effect of solubilisation of methyl esters with different chains of medium length into the binary surfactant system tetradecyldimethylamine oxide/water at constant surfactant concentration of 200 mM. As esters we employed valeric, capronic, enanthic, and pelargonic methyl ester, thereby decreasing the polarity. Always a phase sequence L(1)-L(α)-L(1) is observed with increasing ester concentration, where the L(α)-phase increases in extent and goes to much lower temperatures with increasing chain length of the ester. Viscosity measurements show a maximum at intermediate concentrations of additive that is independent of the type of ester. From SANS measurements detailed information about the structural changes occurring during the rod-to-sphere transition in the system of the shortest additive is deduced, which proceeds first through a pronounced rod growth. Interestingly, for the different esters an almost constant value of the volumic solubilisation capacity is observed, in agreement with the relatively constant interfacial tension. For the different esters no effect on the radius and the area requirement at the amphiphilic interface is observed at the solubilisation boundary. The microemulsions present here are spherical aggregates where the ester is partitioned between core and shell. From the SANS and interfacial tension data the effective bending constants of the surfactant monolayers were deduced and they show that the extension of the L(α)-phase is directly related to a corresponding increase in the bending constants of the surfactant/ester monolayers. Copyright © 2011 Elsevier Inc. All rights reserved.

  1. Cholesterol Analogs with Degradation-resistant Alkyl Side Chains Are Effective Mycobacterium tuberculosis Growth Inhibitors.

    Science.gov (United States)

    Frank, Daniel J; Zhao, Yan; Wong, Siew Hoon; Basudhar, Debashree; De Voss, James J; Ortiz de Montellano, Paul R

    2016-04-01

    Cholest-4-en-3-one, whether added exogenously or generated intracellularly from cholesterol, inhibits the growth ofMycobacterium tuberculosiswhen CYP125A1 and CYP142A1, the cytochrome P450 enzymes that initiate degradation of the sterol side chain, are disabled. Here we demonstrate that a 16-hydroxy derivative of cholesterol, which was previously reported to inhibit growth ofM. tuberculosis, acts by preventing the oxidation of the sterol side chain even in the presence of the relevant cytochrome P450 enzymes. The finding that (25R)-cholest-5-en-3β,16β,26-triol (1) (and its 3-keto metabolite) inhibit growth suggests that cholesterol analogs with non-degradable side chains represent a novel class of anti-mycobacterial agents. In accord with this, two cholesterol analogs with truncated, fluorinated side chains have been synthesized and shown to similarly block the growth in culture ofM. tuberculosis.

  2. Oligo(ethylene glycol)-incorporated hybrid linear alkyl side chains for n-channel polymer semiconductors and their effect on the thin-film crystalline structure.

    Science.gov (United States)

    Kim, Ran; Kang, Boseok; Sin, Dong Hun; Choi, Hyun Ho; Kwon, Soon-Ki; Kim, Yun-Hi; Cho, Kilwon

    2015-01-28

    Oligo(ethylene glycol)-incorporated hybrid linear alkyl side chains, serving as solubilizing groups, are designed and introduced into naphthalene-diimide-based n-channel copolymers. The synthesized polymers exhibit unipolar n-type operation with an electron mobility of up to 1.64 cm(2) V(-1) s(-1), which demonstrates the usefulness of the hybrid side chains in polymer electronics applications.

  3. Nickel-Catalyzed C–O Bond-Cleaving Alkylation of Esters: Direct Replacement of the Ester Moiety by Functionalized Alkyl Chains

    KAUST Repository

    Liu, Xiangqian

    2017-06-07

    Two efficient protocols for the nickel-catalyzed aryl–alkyl cross-coupling reactions using esters as coupling components have been established. The methods enable the selective oxidative addition of nickel to acyl C–O and aryl C–O bonds and allow the aryl–alkyl cross-coupling via decarbonylative bond cleavage or through cleavage of a C–O bond with high efficiency and good functional group compatibility. The protocols allow the streamlined, unconventional utilization of widespread ester groups and their precursors, carboxylic acids and phenols, in synthetic organic chemistry.

  4. Aquatic toxicity and biodegradability of advanced cationic surfactant APA-22 compatible with the aquatic environment.

    Science.gov (United States)

    Yamane, Masayuki; Toyo, Takamasa; Inoue, Katsuhisa; Sakai, Takaya; Kaneko, Youhei; Nishiyama, Naohiro

    2008-01-01

    Cationic surfactant is a chemical substance used in hair conditioner, fabric softener and other household products. By investigating the relationship between the aquatic toxicity and the chemical structures of two types of mono alkyl cationic surfactants, alkyl trimethylammonium salts and alkyl dimethylamine salts, we have found that the C22 alkyl chain length is effective to reduce the toxicity. Besides, we have recognized that the amidopropyl functional group contributes to the enhanced biodegradability by investigating the biodegradation trend of (alkylamidopropyl)dimethylamine salt (alkyl chain length: C18). Based on these findings, we have developed mono alkyl cationic surfactant called APA-22, N-[3-(dimethylamino)propyl]docosanamide salt. APA-22 is formed by the C22 alkyl chain, amidopropyl functional group and di-methyltertiary amine group. We evaluated the aerobic and anaerobic biodegradability of APA-22 by two standard methods (OECD Test Guideline 301B and ECETOC technical document No.28) and found that this substance was degraded rapidly in both conditions. The toxicity to algae, invertebrate and fish of this substance are evaluated by using OECD Test Guideline 201, 202 and 203, respectively. All acute toxicity values are >1 mg/L, which indicates that environmental toxicity of this substance is relatively less toxic to aquatic organism. In addition, we estimated the biodegradation pathway of APA-22 and observed the complete disappearance of APA-22 and its intermediates during the test periods. Based on the environmental data provided above, we concluded that APA22 is more compatible with the aquatic environment compared to other cationic surfactants with mono long alkyl chain.

  5. Effects of alkyl chain length and substituent pattern of fullerene bis-adducts on film structures and photovoltaic properties of bulk heterojunction solar cells.

    Science.gov (United States)

    Tao, Ran; Umeyama, Tomokazu; Kurotobi, Kei; Imahori, Hiroshi

    2014-10-08

    A series of alkoxycarbonyl-substituted dihydronaphthyl-based [60]fullerene bis-adduct derivatives (denoted as C2BA, C4BA, and C6BA with the alkyl chain of ethyl, n-butyl, and n-hexyl, respectively) have been synthesized to investigate the effects of alkyl chain length and substituent pattern of fullerene bis-adducts on the film structures and photovoltaic properties of bulk heterojunction polymer solar cells. The shorter alkyl chain length caused lower solubility of the fullerene bis-adducts (C6BA > C4BA > C2BA), thereby resulting in the increased separation difficulty of respective bis-adduct isomers. The device performance based on poly(3-hexylthiophene) (P3HT) and the fullerene bis-adduct regioisomer mixtures was enhanced by shortening the alkyl chain length. When using the regioisomerically separated fullerene bis-adducts, the devices based on trans-2 and a mixture of trans-4 and e of C4BA exhibited the highest power conversion efficiencies of ca. 2.4%, which are considerably higher than those of the C6BA counterparts (ca. 1.4%) and the C4BA regioisomer mixture (1.10%). The film morphologies as well as electron mobilities of the P3HT:bis-adduct blend films were found to affect the photovoltaic properties considerably. These results reveal that the alkyl chain length and substituent pattern of fullerene bis-adducts significantly influence the photovoltaic properties as well as the film structures of bulk heterojunction solar cells.

  6. Influence of the cation alkyl chain length of imidazolium-based room temperature ionic liquids on the dispersibility of TiO{sub 2} nanopowders

    Energy Technology Data Exchange (ETDEWEB)

    Wittmar, Alexandra; Gajda, Martyna [Universitaet Duisburg-Essen, Lehrstuhl fuer Technische Chemie II (Germany); Gautam, Devendraprakash; Doerfler, Udo; Winterer, Markus [Universitaet Duisburg-Essen, Nanoparticle Process Technology (Germany); Ulbricht, Mathias, E-mail: mathias.ulbricht@uni-due.de [Universitaet Duisburg-Essen, Lehrstuhl fuer Technische Chemie II (Germany)

    2013-03-15

    The influence of the length of the cation alkyl chain on the dispersibility by ultrasonic treatment of TiO{sub 2} nanopowders in hydrophilic imidazolium-based room temperature ionic liquids was studied for the first time by dynamic light scattering and advanced rheology. TiO{sub 2} nanopowders had been synthesized by chemical vapor synthesis (CVS) under varied conditions leading to two different materials. A commercial nanopowder had been used for comparison. Characterizations had been done using transmission electron microscopy, X-ray diffraction, nitrogen adsorption with BET analysis, and FT-IR spectroscopy. Primary particle sizes were about 6 and 8 nm for the CVS-based and 26 nm for the commercial materials. The particle size distribution in the dispersion was strongly influenced by the length of the cation alkyl chain for all the investigated powders with different structural characteristics and concentrations in the dispersion. It was found that an increase of the alkyl chain length was beneficial, leading to a narrowing of the particle size distribution and a decrease of the agglomerate size in dispersion. The smallest average nanoparticle sizes in dispersion were around 30 nm. Additionally, the surface functionality of the nanoparticles, the concentration of the solid material in the liquid, and the period of ultrasonic treatment control the dispersion quality, especially in the case of the ionic liquids with the shorter alkyl chain. The influence of the nanopowders characteristics on their dispersibility decreases considerably with increasing cation alkyl chain length. The results indicate that ionic liquids with adapted structure are candidates as absorber media for nanoparticles synthesized in gas phase processes to obtain liquid dispersions directly without redispergation.

  7. Manipulating the morphology and textural property of γ-AlOOH by modulating the alkyl chain length of cation in ionic liquid

    Energy Technology Data Exchange (ETDEWEB)

    Tang, Zhe, E-mail: tangzhe1983@163.com; Hu, Xiaofu, E-mail: hjj19850922@126.cn; Liang, Jilei, E-mail: liang.jilei_ttplan@126.com; Zhao, Jinchong, E-mail: Dr.zhaojc@gmail.com; Liu, Yunqi, E-mail: liuyq@upc.edu.cn; Liu, Chenguang, E-mail: cgliu@upc.edu.cn

    2013-06-01

    Graphical abstract: - Highlights: • γ-AlOOH was the only product in all experiments. • Different morphology of γ-AlOOH was obtained according to the alkyl chain length. • The textural property of γ-AlOOH was changed according to the alkyl chain length. • The possible formation mechanisms for hollow sphere and microflower were proposed. - Abstract: We demonstrated that the morphology and textural property of γ-AlOOH can be tuned by modulating the alkyl chain length of cation in [C{sub n}mim]{sup +}Cl{sup −} (n = 4, 8, 16). Using the short alkyl chain length-based [C{sub 4}mim]{sup +}Cl{sup −} as the structure-directed reagent, the morphology of γ-AlOOH was not changed and preserved as the hollow sphere structure in all experiments. The specific area and the number of small meso-pores of γ-AlOOH increased with the increase of [C{sub 4}mim]{sup +}Cl{sup −} dosage. While, using the larger alkyl chain length-based ionic liquids as the soft-template, such as [C{sub 8}mim]{sup +}Cl{sup −} and [C{sub 16}mim]{sup +}Cl{sup −}, the morphologies of γ-AlOOH were changed from initiative hollow spheres into the final microflowers. The specific areas of γ-AlOOH firstly increased then decreased with the increase of their dosage. The samples were characterized by X-ray Diffraction (XRD), Fourier Transform Infrared Spectroscopy (FT-IR), Scanning Electron Microscope (SEM) and Transmission Electron Microscopy (TEM). Furthermore, the possible formation mechanisms of γ-AlOOH have been proposed.

  8. Effect of surfactants on the fluorescence spectra of water-soluble MEHPPV derivatives having grafted polyelectrolyte chains

    Indian Academy of Sciences (India)

    Nagesh Kolishetti; S Ramakrishnan

    2007-03-01

    Poly(2-methoxy-5-[2'-ethylhexyoxy]-1,4-phenylenevinylene) (MEHPPV) derivatives with polyacrylic acid (PAA) chains grafted onto their backbone were found to be water soluble, and they exhibited a dramatic increase in their fluorescence intensity in the presence of a variety of surfactants, even at concentrations far below their critical micelle concentrations (CMC). This increase was accompanied by a blue-shift in the emission maximum. These observations are rationalized based on the postulate that the backbone conformation of the conjugated polymer is modulated upon interaction of the surfactant molecules with the polyelectrolytic tethers, which in turn results in a significant depletion of intra-chain interchromophore interactions that are known to cause red-shifted emission bands with significantly lower emission yields.

  9. Dielectric relaxation of alkyl chains in graphite oxide and n-alkylammonium halides

    Science.gov (United States)

    Ai, Xiaoqian; Tian, Yuchen; Gu, Min; Yu, Ji; Tang, Tong B.

    2016-05-01

    The dynamic of n-alkylammonium halides and n-alkylammonium cations (n = 12, 14, 16, 18) intercalated in graphite oxide (GO) have been investigated with complex impedance spectroscopy. X-ray diffraction, X-ray photoelectron spectroscopy, Fourier-transform infrared spectroscopy, elemental analysis and thermogravimetry served to characterize the materials. The intercalated alkylammonium cations distributes as monolayers (when n = 12, 14 or 16) or bilayers (when n = 18), with their long axis parallel to GO layers, and with cations of headgroups bonded ionically to C-O- groups of GO; backbones of the confined molecules remain free. All halides and intercalation compounds suffer dielectric loss at low temperature. Arrhenius plots of the thermal dependence of the loss peaks, which are asymmetric, produce apparent activation energies that rise with increasing n. Ngai's correlated-state model helps to correct for effects of dipole-dipole interaction, leading to virtually identical values for actual activation energy of 110 meV ± 5%; the values are also almost the same as the barrier energy for internal rotation in the alkyl macromolecule. We conclude that the relaxation of the alkylammonium cations arises not from C3 reorientation of the CH3 at its headgroup, but from small-angle wobbling around its major axis, an intrinsic motion.

  10. Preparation, stability and two-dimensional ordered arrangement of gold nanoparticles capped by surfactants with different chain lengths

    Institute of Scientific and Technical Information of China (English)

    周学华; 李津如; 刘春艳; 江龙

    2002-01-01

    Gold nanoparticles modified with C10NH2, C12NH2, C16NH2 and C18NH2 respectively have been prepared by the reverse micelle method. Nanoparticles stability and their two-dimensional (2D) ordered arrangement were studied by UV-Vis absorption spectra and LB technique. The factors, such as the chain length and the size distribution of particles, which affect the 2D ordered arrangement formation, are discussed. Experimental results show that the longer the chain length of surfactants capping the gold nanoparticles, the more stable the nanoparticles, and the more ordered 2D arrangement of gold nanoparticles.

  11. Effect of Gemini-type surfactant on methane hydrate formation

    Energy Technology Data Exchange (ETDEWEB)

    Jeong, K.E.; Park, J.M.; Kim, C.U.; Chae, H.J.; Jeong, S.Y. [Korea Research Inst. of Chemical Technology, Jang-Dong, Yuseong-Gu, Daejeon (Korea, Republic of)

    2008-07-01

    Natural gas hydrates are formed from water and natural gas molecules at particular temperatures and pressures that become ice-like inclusion compounds. Gas hydrates offer several benefits such as energy resource potential and high storage capacity of natural gas in the form of hydrates. However, the application of natural gas hydrates has been deterred by its low formation rate and low conversion ratio of water into hydrate resulting in low actual storage capacity. This paper presented an experimental study to determine the effect of adding a novel Gemini-type surfactant on methane hydrate formation. The experimental study was described with reference to the properties of prepared diols and properties of prepared disulfonates. Gemini surfactant is the family of surfactant molecules possessing more than one hydrophobic tail and hydrophilic head group. They generally have better surface-active properties than conventional surfactants of equal chain length. The paper presented the results of the study in terms of the reactions of diols with propane sultone; storage capacity of hydrate formed with and without surfactant; and methane hydrate formation with and without disulfonate. It was concluded that the methane hydrate formation was accelerated by the addition of novel anionic Gemini-type surfactants and that hydrate formation was influenced by the surfactant concentration and alkyl chain length. For a given concentration, the surfactant with the highest chain length demonstrated the highest formation rate and storage capacity. 5 refs., 3 tabs., 4 figs.

  12. Effect of Difference in Fatty Acid Chain Lengths of Medium- Chain Lipids on Lipid/Surfactant/Water Phase Diagrams and Drug Solubility

    Directory of Open Access Journals (Sweden)

    Hetal N. Prajapati

    2011-09-01

    Full Text Available Lipids consisting of medium chain fatty acids are commonly used in the development of lipid-based selfemulsifying and self-microemulsifying drug delivery systems. However, no systematic approach to selecting one lipid over another has been reported in the literature. In this study, propylene glycol (PG monoester (PG monocaprylate, Capmul PG-8® and PG diester (PG dicaprylocaprate, Captex 200P® of C8-fatty acids were compared with PG monoester (PG monolaurate, Capmul PG-12® and PG diester (PG dilaurate, Capmul PG-2L® of C12-fatty acids with respect to their phase diagrams, and especially for their ability to form microemulsions in the presence of a common surfactant, Cremophor EL®, and water. The solubility of two model drugs, danazol and probucol, in the lipids and lipid/surfactant mixtures were also compared. The effect of the chain length of medium-chain fatty acids (C8 versus C12 on the phase diagrams of the lipids was minimal. Both shorter and longer chain lipids formed essentially similar microemulsion and emulsion regions in the presence of Cremophor EL® and water, although the C12-fatty acid esters formed larger gel regions in the phase diagrams than the C8-fatty acid esters. When monoesters were mixed with their respective diesters at 1:1 ratios, larger microemulsion regions with lower lipid particle sizes were observed compared to those obtained with individual lipids alone. While the solubility of both danazol and probucol increased greatly in all lipids studied, compared to their aqueous solubility, the solubility in C12-fatty acid esters was found to be lower than in C8-fatty acid esters when the lipids were used alone. This difference in solubility due to the difference in fatty acid chain length, practically disappeared when the lipids were combined with the surfactant.

  13. Effect of presence of benzene ring in surfactant hydrophobic chain on the transformation towards one dimensional aggregate

    Directory of Open Access Journals (Sweden)

    Rabah A. Khalil

    2015-07-01

    Full Text Available The formation of wormlike micelle and the following significant changes in rheological properties suffer misunderstanding from both theoretical and fundamental aspects. Recently, we have introduced a theory for interpreting such important phenomenon which is referred to as critical intermolecular forces (CIF. The theory has stated that the hydrophobic effect is the main factor for the formation of worm-like aggregates. Therefore, it seems interesting to check out the validity of this new physical insight through investigating the presence of benzene ring as less hydrophobic group in contrast to that of alkyl in surfactant tail. The mixture of anionic sodium dodecylbenzenesulphonate (SDBS and cationic cetyltrimethylammonium bromide (CTAB shows a high dynamic viscosity peak at the ratio of 80/20 of 3 wt.% CTAB/SDBS indicating the formation of wormlike micelles. The thermodynamic properties have been evaluated for this mixture exhibiting good agreement with the rheological changes. Interestingly, the results show the presence of benzene ring (in SDBS causing a negative effect towards the formation of one dimensional aggregate in contrast to previous results which support the proposed CIF theory. The presence of nonionic surfactant TritonX-100 in binary and ternary systems of SDBS and CTAB prohibits the formation of wormlike micelles.

  14. Preparation of the pyridinium salts differing in the length of the N-alkyl substituent.

    Science.gov (United States)

    Marek, Jan; Stodulka, Petr; Cabal, Jiri; Soukup, Ondrej; Pohanka, Miroslav; Korabecny, Jan; Musilek, Kamil; Kuca, Kamil

    2010-03-19

    Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents.

  15. Preparation of the Pyridinium Salts Differing in the Length of the N-Alkyl Substituent

    Directory of Open Access Journals (Sweden)

    Kamil Musilek

    2010-03-01

    Full Text Available Quaternary pyridinium salts with chains ranging from C8 to C20 belong in the large group of cationic surfactants. In this paper, the preparation of such cationic surface active agents based on the pyridinium moiety and differing in the length of the N-alkyl chain is described. Additionally, HPLC technique was established to distinguish each prepared pyridinium analogue. This study represents universal method for preparation and identification of quaternary pyridinium detergents.

  16. Gemini ester quat surfactants and their biological activity.

    Science.gov (United States)

    Łuczyński, Jacek; Frąckowiak, Renata; Włoch, Aleksandra; Kleszczyńska, Halina; Witek, Stanisław

    2013-03-01

    Cationic gemini surfactants are an important class of surface-active compounds that exhibit much higher surface activity than their monomeric counterparts. This type of compound architecture lends itself to the compound being easily adsorbed at interfaces and interacting with the cellular membranes of microorganisms. Conventional cationic surfactants have high chemical stability but poor chemical and biological degradability. One of the main approaches to the design of readily biodegradable and environmentally friendly surfactants involves inserting a bond with limited stability into the surfactant molecule to give a cleavable surfactant. The best-known example of such a compound is the family of ester quats, which are cationic surfactants with a labile ester bond inserted into the molecule. As part of this study, a series of gemini ester quat surfactants were synthesized and assayed for their biological activity. Their hemolytic activity and changes in the fluidity and packing order of the lipid polar heads were used as the measures of their biological activity. A clear correlation between the hemolytic activity of the tested compounds and their alkyl chain length was established. It was found that the compounds with a long hydrocarbon chain showed higher activity. Moreover, the compounds with greater spacing between their alkyl chains were more active. This proves that they incorporate more easily into the lipid bilayer of the erythrocyte membrane and affect its properties to a greater extent. A better understanding of the process of cell lysis by surfactants and of their biological activity may assist in developing surfactants with enhanced selectivity and in widening their range of application.

  17. Thermodynamics of non-ionic surfactant Triton X-100-cationic surfactants mixtures at the cloud point

    Energy Technology Data Exchange (ETDEWEB)

    Batigoec, Cigdem [Department of Chemistry, Faculty of Sciences, Trakya University, 22030 Edirne (Turkey); Akbas, Halide, E-mail: hakbas34@yahoo.com [Department of Chemistry, Faculty of Sciences, Trakya University, 22030 Edirne (Turkey); Boz, Mesut [Department of Chemistry, Faculty of Sciences, Trakya University, 22030 Edirne (Turkey)

    2011-12-15

    Highlights: > Non-ionic surfactants are used as emulsifier and solubilizate in such as textile, detergent and cosmetic. > Non-ionic surfactants occur phase separation at temperature as named the cloud point in solution. > Dimeric surfactants have attracted increasing attention due to their superior surface activity. > The positive values of {Delta}G{sub cp}{sup 0} indicate that the process proceeds nonspontaneous. - Abstract: This study investigates the effects of gemini and conventional cationic surfactants on the cloud point (CP) of the non-ionic surfactant Triton X-100 (TX-100) in aqueous solutions. Instead of visual observation, a spectrophotometer was used for measurement of the cloud point temperatures. The thermodynamic parameters of these mixtures were calculated at different cationic surfactant concentrations. The gemini surfactants of the alkanediyl-{alpha}-{omega}-bis (alkyldimethylammonium) dibromide type, on the one hand, with different alkyl groups containing m carbon atoms and an ethanediyl spacer, referred to as 'm-2-m' (m = 10, 12, and 16) and, on the other hand, with -C{sub 16} alkyl groups and different spacers containing s carbon atoms, referred to as '16-s-16' (s = 6 and 10) were synthesized, purified and characterized. Additions of the cationic surfactants to the TX-100 solution increased the cloud point temperature of the TX-100 solution. It was accepted that the solubility of non-ionic surfactant containing polyoxyethylene (POE) hydrophilic chain was a maximum at the cloud point so that the thermodynamic parameters were calculated at this temperature. The results showed that the standard Gibbs free energy ({Delta}G{sub cp}{sup 0}), the enthalpy ({Delta}H{sub cp}{sup 0}) and the entropy ({Delta}S{sub cp}{sup 0}) of the clouding phenomenon were found positive in all cases. The standard free energy ({Delta}G{sub cp}{sup 0}) increased with increasing hydrophobic alkyl chain for both gemini and conventional cationic

  18. The Effects of Surfactants on the Desorption of Organic Contaminants from Aquifer Materials

    Science.gov (United States)

    1989-08-01

    Wilmington Delaware, April 11, 1989. Cox, M. F. and K. L. Matheson. "Interactions between Linear Alkylbenzene Sulfonates and Water Hardness Ions. II. Reducing...Between Linear Alkylbenzene Sulfonates and Water Hardness Ions. I. Effect of Calcium Ion on Surfactant Solubility and Implications for Detergency...Fatty acids Sulfonate Paraffins Sulfate Olefins Carboxylate Alkylbenzenes Quaternary ammonium Long chain alcohols Protonated amine Alkyl Phenols

  19. Light-Induced ESR Studies of Quadrimolecular Recombination Kinetics of Photogenerated Charge Carriers in Regioregular Poly(3-alkylthiophene)/C60 Composites: Alkyl Chain Dependence

    Science.gov (United States)

    Tanaka, Hisaaki; Hasegawa, Naoki; Sakamoto, Tomotaka; Marumoto, Kazuhiro; Kuroda, Shin-ichi

    2007-08-01

    Light-induced ESR (LESR) measurements have been performed on the composites of regioregular poly(3-alkylthiophene) (RR-P3AT) and C60 by using polymers having different alkyl chains (CmH2m+1 with m=6, 8, 10, 12). The quadrimolecular recombination (QR) kinetics of photogenerated charge carriers, previously reported, have been confirmed for all the composites from the excitation power (Iex) dependence of the LESR intensity showing an ˜Iex0.25 dependence. The time decay of LESR intensity is also consistent with the QR model. Considering that only bimolecular recombination is observed in regiorandom polymer composites, the occurrence of QR strongly suggests the formation of doubly charged states, either bipolarons or polaron pairs on the regioregular polymer chains. On the other hand, the QR rate constant γ has been found to exhibit weak alkyl chain dependence, contrary to the case of the field-effect mobility of pure regioregular polymers with systematic alkyl chain dependence. This implies the significant contribution of the polymer and fullerene interface in determining γ.

  20. Dynamic interfacial tension behavior of alkyl amino sulfonate in crude oil-brine system

    Energy Technology Data Exchange (ETDEWEB)

    Ren, Zhao Hua; Luo, Yue [Yangtze Univ., Jingzhou, Hubei (China). College of Chemistry and Environmental Engineering

    2013-09-15

    The compatibility of surfactants, a series of alkyl amino sulfonate containing various the length of alkyl chain (dodecyl, tetradecyl, hexadecyl and octadecyl, developed in our laboratory), with formation water matching the Xinjiang Oil Field reservoir water and the dynamic interfacial tensions (DIT) behaviors between the crude oil and the formation water for a number of alkaline flooding systems were measured. These surfactants are found to be well compatible with formation water up to 0.10g L{sup -1} surfactant concentration, especially Dodec-AS and Tetradec-AS show a good compatibility with formation water over the full range of surfactant concentration investigated (0.01-0.20g L{sup -1}). All surfactants exhibit the dynamic interfacial tension behavior, and can reach and maintain low interfacial tension at very low concentration. The time for reaching the equilibrium DIT (DIT{sub eq}) is longer for surfactant with stronger lipophilicity, e.g. octadecyl-AS. It is interestingly found that the ratio value between DIT{sub eq} and the tension at crude oil/reservoir water interface in the absence of surfactant is in the range of 10{sup -4}-10{sup -3} mN m{sup -1}, accordingly based on which and the previous results, four surfactants individually or with other additives together may become potent candidates for enhanced oil recovery. Fortunately, the alkyl amino sulfonate combinational systems without alkali designed by our group can reduce the interfacial tension even to 10{sup -4} mN m{sup -1} at very low surfactant concentration. These surfactants or their systems have characteristic of 'Green', in addition to the excellent salt-tolerance and the less expensive cost for enhanced oil recovery, and therefore they are good oil-displacing reagents for enhanced oil recovery. (orig.)

  1. Effects of Odd–Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure

    KAUST Repository

    Akkerman, Hylke B.

    2013-07-31

    Because of their preferential two-dimensional layer-by-layer growth in thin films, 5,5′bis(4-alkylphenyl)-2,2′-bithiophenes (P2TPs) are model compounds for studying the effects of systematic chemical structure variations on thin-film structure and morphology, which in turn, impact the charge transport in organic field-effect transistors. For the first time, we observed, by grazing incidence X-ray diffraction (GIXD), a strong change in molecular tilt angle in a monolayer of P2TP, depending on whether the alkyl chain on the P2TP molecules was of odd or even length. The monolayers were deposited on densely packed ultrasmooth self-assembled alkane silane modified SiO2 surfaces. Our work shows that a subtle change in molecular structure can have a significant impact on the molecular packing structure in thin film, which in turn, will have a strong impact on charge transport of organic semiconductors. This was verified by quantum-chemical calculations that predict a corresponding odd-even effect in the strength of the intermolecular electronic coupling. © 2013 American Chemical Society.

  2. Synthesis of a series of soluble main-chain chiral nonracemic poly(alkyl-aryl ketone

    Directory of Open Access Journals (Sweden)

    2008-06-01

    Full Text Available A series of main-chain chiral polyketones have been synthesized through condensation polymerization of a dihalide and a diketone with optically pure binaphthyl moiety as linkage in the polymer backbone. The solubility of the polymers can be easily enhanced by substituents at the alpha position next to the carbonyl groups. Reducing the steric hindrance of the substituents in the monomers increases the reactivity of the polymerization. The chiral polymers exhibit large optical rotations. Circular Dichroism (CD spectra of the polymers are similar to those of the corresponding monomers. The novel synthetic strategy may have great impact on future development of palladium catalyzed condensation polymerizations. The highly soluble chiral polymers synthesized allow for preparation of materials in the form of thin films and have potentials applications in various areas such as chiral separation and recognition.

  3. Theoretical investigation on the kinetics and mechanisms of hydroxyl radical-induced transformation of parabens and its consequences for toxicity: Influence of alkyl-chain length.

    Science.gov (United States)

    Gao, Yanpeng; Ji, Yuemeng; Li, Guiying; An, Taicheng

    2016-03-15

    As emerging organic contaminants (EOCs), the ubiquitous presence of preservative parabens in water causes a serious environmental concern. Hydroxyl radical ((•)OH) is a strong oxidant that can degrade EOCs through photochemistry in surface water environments as well as in advanced oxidation processes (AOPs). To better understand the degradation mechanisms, kinetics, and products toxicity of the preservative parabens in aquatic environments and AOPs, the (•)OH-initiated degradation reactions of the four parabens were investigated systematically using a computational approach. The four studied parabens with increase of alkyl-chain length were methylparaben (MPB), ethylparaben (EPB), propylparaben (PPB), and dibutylparaben (BPB). Results showed that the four parabens can be initially attacked by (•)OH through (•)OH-addition and H-abstraction routes. The (•)OH-addition route was more important for the degradation of shorter alkyl-chain parabens like MPB and EPB, while the H-abstraction route was predominant for the degradation of parabens with longer alkyl-chain for example PPB and BPB. In assessing the aquatic toxicity of parabens and their degradation products using the model calculations, the products of the (•)OH-addition route were found to be more toxic to green algae than original parabens. Although all degradation products were less toxic to daphnia and fish than corresponding parental parabens, they could be still harmful to these aquatic organisms. Furthermore, as alkyl-chain length increased, the ecotoxicity of parabens and their degradation products was found to be also increased. Copyright © 2016 Elsevier Ltd. All rights reserved.

  4. Diacyltransferase Activity and Chain Length Specificity of Mycobacterium tuberculosis PapA5 in the Synthesis of Alkyl β-Diol Lipids

    Energy Technology Data Exchange (ETDEWEB)

    Touchette, Megan H.; Bommineni, Gopal R.; Delle Bovi, Richard J.; Gadbery, John; Nicora, Carrie D.; Shukla, Anil K.; Kyle, Jennifer E.; Metz, Thomas O.; Martin, Dwight W.; Sampson, Nicole S.; Miller, W. T.; Tonge, Peter J.; Seeliger, Jessica C.

    2015-09-08

    Although classified as Gram-positive bacteria, Corynebacterineae possess an asymmetric outer membrane that imparts structural and thereby physiological similarity to more distantly related Gram-negative bacteria. Like lipopolysaccharide in Gram-negative bacteria, lipids in the outer membrane of Corynebacterineae have been associated with the virulence of pathogenic species such as Mycobacterium tuberculosis (Mtb). For example, Mtb strains that lack long, branched-chain alkyl esters known as dimycocerosates (DIMs) are significantly attenuated in model infections. The resultant interest in the biosynthetic pathway of these unusual virulence factors has led to the elucidation of many of the steps leading to the final esterification of the alkyl beta-diol, phthiocerol, with branched-chain fatty acids know as mycocerosates. PapA5 is an acyltransferase implicated in these final reactions. We here show that PapA5 is indeed the terminal enzyme in DIM biosynthesis by demonstrating its dual esterification activity and chain-length preference using synthetic alkyl beta-diol substrate analogues. Applying these analogues to a series of PapA5 mutants, we also revise a model for the substrate binding within PapA5. Finally, we demonstrate that the Mtb Ser/Thr kinase PknB modifies PapA5 on three Thr residues, including two (T196, T198) located on an unresolved loop. These results clarify the DIM biosynthetic pathway and suggest possible mechanisms by which DIM biosynthesis may be regulated by the post-translational modification of PapA5.

  5. Prediction and determination of the stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, a microbial metabolite.

    Science.gov (United States)

    Yoshimura, Aya; Kishimoto, Shinji; Nishimura, Shinichi; Otsuka, Saori; Sakai, Yuki; Hattori, Akira; Kakeya, Hideaki

    2014-08-01

    For the prediction of the relative stereochemistry of 1,3-dimethyl substitution in alkyl chains, a simple approach based on (1)H NMR data was recently proposed; Δδ values of methylene protons located between methyl-substituted methine carbons can be diagnostic for predicting it. Here we applied this empirical "geminal proton rule" to verucopeptin, a lipopeptide from Streptomyces sp. To determine the absolute stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, we converted the corresponding alkyl chain to a carboxylic acid by oxidative cleavage. The geminal proton rule clearly predicted the relative stereochemistry as 31S*,33S*,35R*. This prediction was definitely confirmed by synthesizing four possible diastereomers and comparing their NMR spectra. Furthermore, we reinvestigated the geminal proton rule using reported compounds and our synthesized compounds. Our result strongly suggests that the rule was solid, at least for predicting the stereochemistry of 2,4-dimethylated and 2,4,6-trimethylated fatty acids.

  6. Heat evolution of micelle formation, dependence of enthalpy, and heat capacity on the surfactant chain length and head group.

    Science.gov (United States)

    Opatowski, Ella; Kozlov, Michael M; Pinchuk, Ilya; Lichtenberg, Dov

    2002-02-15

    Micelle formation by many surfactants is endothermic at low temperatures but exothermic at high temperatures. In this respect, dissociation of micelles (demicellization) is similar to dissolving hydrocarbons in water. However, a remarkable difference between the two processes is that dissolving hydrocarbons is isocaloric at about 25 degrees C, almost independently of the hydrocarbon chain length, whereas the temperature (T*) at which demicellization of different surfactants is athermal varies over a relatively large range. We have investigated the temperature dependence of the heat of demicellization of three alkylglucosides with hydrocarbon chains of 7, 8, and 9 carbon atoms. At about 25 degrees C, the heat of demicellization of the three studied alkylglucosides varied within a relatively small range (DeltaH=-7.8+/-0.4 kJ/mol). The temperature dependence of DeltaH(demic) indicates that within the studied temperature range the heat capacity of demicellization (DeltaC(P,demic)) is about constant. The value of DeltaC(P,demic) exhibited an apparently linear dependence on the surfactant's chain length (DeltaC(P,demic)/n(CH(2))=47+/-7 kJ/mol K). Our interpretation of these results is that (i) the transfer of the head groups from micelles to water is exothermic and (ii) the temperature dependence of the heat associated with water-hydrocarbon interactions is only slightly affected by the head group. This implies that the deviation of the value of T* from 25 degrees C results from the contribution of the polar head to the overall heat of demicellization. Calorimetric studies of other series of amphiphiles will have to be conducted to test whether the latter conclusion is general.

  7. Sequence-specific DNA alkylation and transcriptional inhibition by long-chain hairpin pyrrole-imidazole polyamide-chlorambucil conjugates targeting CAG/CTG trinucleotide repeats.

    Science.gov (United States)

    Asamitsu, Sefan; Kawamoto, Yusuke; Hashiya, Fumitaka; Hashiya, Kaori; Yamamoto, Makoto; Kizaki, Seiichiro; Bando, Toshikazu; Sugiyama, Hiroshi

    2014-09-01

    Introducing novel building blocks to solid-phase peptide synthesis, we readily synthesized long-chain hairpin pyrrole-imidazole (PI) polyamide-chlorambucil conjugates 3 and 4 via the introduction of an amino group into a GABA (γ-turn) contained in 3, to target CAG/CTG repeat sequences, which are associated with various hereditary disorders. A high-resolution denaturing polyacrylamide sequencing gel revealed sequence-specific alkylation both strands at the N3 of adenines or guanines in CAG/CTG repeats by conjugates 3 and 4, with 11bp recognition. In vitro transcription assays using conjugate 4 revealed that specific alkylation inhibited the progression of RNA polymerase at the alkylating sites. Chiral substitution of the γ-turn with an amino group resulted in higher binding affinity observed in SPR assays. These assays suggest that conjugates 4 with 11bp recognition has the potential to cause specific DNA damage and transcriptional inhibition at the alkylating sites. Copyright © 2014 Elsevier Ltd. All rights reserved.

  8. Amphiphilic Ruthenium(II Terpyridine Sensitizers with Long Alkyl Chain Substituted β-Diketonato Ligands: An Efficient Coadsorbent-Free Dye-Sensitized Solar Cells

    Directory of Open Access Journals (Sweden)

    Ashraful Islam

    2011-01-01

    Full Text Available Three alkyl-substituted β-diketonato-ruthenium(II-polypyridyl sensitizers with different alkyl chain lengths, [Ru(tctpy(tfpd(NCS] (A1, [Ru(tctpy(tfdd(NCS] (A2, and [Ru(tctpy(tfid(NCS] (A3, were designed and synthesized for dye-sensitized solar cells (DSCs to investigate the effect of bulky alkyl chain substituents on the photovoltaic performances (where tctpy = 4,4′,4′′-tricarboxy-2,2′:;6′,2′′-terpyridine, tfpd =1,1,1-trifluoropentane-2,4-dione, tfdd = 1,1,1-trifluorodecane-2,4-dione, and tfid =1,1,1-trifluoroicosane-2,4-dione. These complexes exhibit a broad metal-to-ligand charge transfer absorption band over the whole visible range extending up to 950 nm. All complexes were examined in the presence and absence of the coadsorbent deoxycholic acid (DCA in dye-bath solutions. These sensitizers, when anchored to nanocrystalline TiO2 films, achieve efficient sensitization to TiO2 electrodes. Under standard AM 1.5 sunlight, the complex A3 containing long alkyl chain length of C16 yielded a short-circuit photocurrent density of 18.0 mA/cm2, an open-circuit voltage of 0.64 V, and a fill factor of 0.66, corresponding to an overall conversion efficiency of 7.6% in the absence of DCA. The power conversion efficiency of A1 sensitized DSCs was significantly increased upon the addition of DCA as compared to that in the absence of DCA. However, the photovoltaic performance of A3 was not dependent on DCA at all, probably due to the inherent structural nature of the A3 molecule.

  9. Bis(thienothiophenyl) diketopyrrolopyrrole-based conjugated polymers with various branched alkyl side chains and their applications in thin-film transistors and polymer solar cells.

    Science.gov (United States)

    Shin, Jicheol; Park, Gi Eun; Lee, Dae Hee; Um, Hyun Ah; Lee, Tae Wan; Cho, Min Ju; Choi, Dong Hoon

    2015-02-11

    New thienothiophene-flanked diketopyrrolopyrrole and thiophene-containing π-extended conjugated polymers with various branched alkyl side-chains were successfully synthesized. 2-Octyldodecyl, 2-decyltetradecyl, 2-tetradecylhexadecyl, 2-hexadecyloctadecyl, and 2-octadecyldocosyl groups were selected as the side-chain moieties and were anchored to the N-positions of the thienothiophene-flanked diketopyrrolopyrrole unit. All five polymers were found to be soluble owing to the bulkiness of the side chains. The thin-film transistor based on the 2-tetradecylhexadecyl-substituted polymer showed the highest hole mobility of 1.92 cm2 V(-1) s(-1) due to it having the smallest π-π stacking distance between the polymer chains, which was determined by grazing incidence X-ray diffraction. Bulk heterojunction polymer solar cells incorporating [6,6]-phenyl-C71-butyric acid methyl ester as the n-type molecule and the additive 1,8-diiodooctane (1 vol %) were also constructed from the synthesized polymers without thermal annealing; the device containing the 2-octyldodecyl-substituted polymer exhibited the highest power conversion efficiency of 5.8%. Although all the polymers showed similar physical properties, their device performance was clearly influenced by the sizes of the branched alkyl side-chain groups.

  10. Emulsion of aqueous-based nonspherical droplets in aqueous solutions by single-chain surfactants: templated assembly by nonamphiphilic lyotropic liquid crystals in water.

    Science.gov (United States)

    Varghese, Nisha; Shetye, Gauri S; Bandyopadhyay, Debjyoti; Gobalasingham, Nemal; Seo, JinAm; Wang, Jo-Han; Theiler, Barbara; Luk, Yan-Yeung

    2012-07-24

    Single-chain surfactants usually emulsify and stabilize oily substances into droplets in an aqueous solution. Here, we report a coassembly system, in which single types of anionic or non-ionic surfactants emulsify a class of water-soluble nonamphiphilic organic salts with fused aromatic rings in aqueous solutions. The nonamphiphilic organic salts are in turn promoted to form droplets of water-based liquid crystals (chromonic liquid crystals) encapsulated by single-chain surfactants. The droplets, stabilized against coalescence by encapsulated in a layer (or layers) of single chain surfactants, are of both nonspherical tactoid (elongated ellipsoid with pointy ends) and spherical shapes. The tactoids have an average long axis of ∼9 μm and a short axis of ∼3.5 μm with the liquid crystal aligning parallel to the droplet surface. The spherical droplets are 5-10 μm in diameter and have the liquid crystal aligning perpendicular to the droplet surface and a point defect in the center. Cationic and zwitterionic surfactants studied in this work did not promote the organic salt to form droplets. These results illustrate the complex interplay of self-association and thermodynamic incompatibility of molecules in water, which can cause new assembly behavior, including potential formation of vesicles or other assemblies, from surfactants that usually form only micelles. These unprecedented tactoidal shaped droplets also provide potential for the fabrication of new soft organic microcapsules.

  11. The acute toxic effects of imidazolium-based ionic liquids with different alkyl-chain lengths and anions on zebrafish (Danio rerio).

    Science.gov (United States)

    Zhang, Cheng; Zhu, Lusheng; Wang, Jinhua; Wang, Jun; Zhou, Tongtong; Xu, Yaqi; Cheng, Chao

    2017-06-01

    With the increasing applications of ionic liquids (ILs), the toxicity of ILs has drawn increasing attention in recent years, especially the influences of different anions and alkyl-chain lengths on the acute toxicity to aquatic organisms. We performed a study on the acute toxicity of 1-alkyl-3-methylimidazolium nitrate ([Cnmim]NO3 (n=2, 4, 6, 8, 10, 12)), 1-hexyl-3-methylimidazolium ILs ([C6mim]R (R=Cl(-), Br(-), BF4(-), PF6(-))) to zebrafish (Danio rerio). We also evaluated the sensibility of the investigated animals and the stability of ILs in water via high performance liquid chromatography (HPLC, Agilent 1260, Agilent Technologies Inc., USA) to prove the reliability of the present study. The results illustrated that the test zebrafish (Danio rerio) were sensitive to the reference toxicant and that the investigated ILs in water were stable. The 50% lethal concentration (LC50) was used to represent the acute toxicity to zebrafish (Danio rerio). The present study showed that the highest toxic IL is [C12mim]NO3 and the lowest toxic IL is [C2mim]NO3 on Danio rerio. The LC50s for ILs with different anions had similar values. Accordingly, we believe that ILs with different alkyl-chain lengths cause greater effects than other anions on acute toxicity to aquatic organisms. Furthermore, the present study can also provide scientific methods for future studies to select and assess ILs.

  12. Aquatic toxicity structure-activity relationships for the zwitterionic surfactant alkyl dimethyl amine oxide to several aquatic species and a resulting species sensitivity distribution.

    Science.gov (United States)

    Belanger, Scott E; Brill, Jessica L; Rawlings, Jane M; McDonough, Kathleen M; Zoller, Ann C; Wehmeyer, Kenneth R

    2016-12-01

    Amine oxide (AO) is a cationically charged surfactant at environmental pH and has previously been assessed in the OECD (Organization for Economic Cooperation and Development) High Production Volume (HPV) chemicals program. Typical of cationic chemicals, AO is highly aquatically toxic. In this study we vastly improve the knowledge of AO toxicity by developing acute Quantitative Structure Activity Relationships (QSARs) for an alga (Desmodesmus subspicatus), an invertebrate (Daphnia magna) and a fish (Danio rerio) using the appropriate array of OECD Test Guidelines. A chronic toxicity QSAR was also determined for the most sensitive taxon, Desmodesmus. Pure AO spanning the chain lengths of C8 to C16 were tested individually with trace analytical confirmation of exposures in all tests. The QSARs were all of high quality (R(2) 0.92-0.98) with slopes ranging from -0.338 to -0.484. QSARs were then used to normalize toxicity outcomes for a larger, previously published data set used in HPV, European REACH (Registration, Evaluation, and Authorization of Chemicals), and peer reviewed publications. Two additional species, Lemna gibba (macrophyte) and Ankistrodesmus falcatus (alga) were studied in exposures to dodecyl (C12) AO to provide sufficient taxonomic diversity to conduct a Species Sensitivity Distribution (SSD) analysis. The SSD 5th percentile hazardous concentration (HC5) to C12 AO was found to be 0.052mg/L which is similar to an existing AO 28-d, 3-community periphyton community bioassay normalized to C12 AO (No-observed-effect-concentration or NOEC=0.152mg/L). The statistical properties of the SSD was probed suggesting that new studies of additional taxa would be required that were at least 10-fold more sensitive than the most sensitive taxon to move the HC5 lower by a factor of 3. The overall AO hazard assessment suggests a large margin of safety relative to published environmental exposure data.

  13. Solution Properties of Dissymmetric Sulfonate-type Anionic Gemini Surfactants.

    Science.gov (United States)

    Yoshimura, Tomokazu; Akiba, Kazuki

    2016-01-01

    Dissymmetric and symmetric anionic gemini surfactants, N-alkyl-N'-alkyl-N,N'dipropanesulfonylethylenediamine (CmCnSul, where m and n represent alkyl chain lengths of m-n = 4-16, 6-14, 8-12, 10-10, and 12-12), were synthesized by two- or three-step reactions. Their physicochemical properties were characterized by equilibrium surface tension measurements, steady-state fluorescence spectroscopy of pyrene, and dynamic light scattering. The critical micelle concentration (CMC) of the dissymmetric surfactants C4C16Sul, C6C14Sul, and C8C12Sul was slightly lower than that of the symmetric surfactant C10C10Sul. The occupied area per molecule (A) of C8C12Sul was smaller than that of C10C10Sul, indicating that C8C12Sul has a high surface activity. However, the increase in the degree of dissymmetry from C8C12Sul to C6C14Sul and then to C4C16Sul resulted in high surface tension and large A. Based on the surface tension, the standard free energies of micellization (∆G°mic) and adsorption (∆G°ads), the efficiency of surface adsorption (pC20), and the effectiveness of surface adsorption (CMC/C20) were obtained. These parameters suggested that C8C12Sul formed micelles more readily than the other surfactants. The properties determined from the surface tension indicated that C8C12Sul's ability is intermediate between those of C10C10Sul and C12C12Sul. The pyrene fluorescence and dynamic light scattering results revealed that the micelle size depends on the longer of the two alkyl chains in dissymmetric surfactants.

  14. Kinetic study of the anaerobic biodegradation of alkyl polyglucosides and the influence of their structural parameters.

    Science.gov (United States)

    Ríos, Francisco; Fernández-Arteaga, Alejandro; Lechuga, Manuela; Jurado, Encarnación; Fernández-Serrano, Mercedes

    2016-05-01

    This paper reports a study of the anaerobic biodegradation of non-ionic surfactants alkyl polyglucosides applying the method by measurement of the biogas production in digested sludge. Three alkyl polyglucosides with different length alkyl chain and degree of polymerization of the glucose units were tested. The influence of their structural parameters was evaluated, and the characteristics parameters of the anaerobic biodegradation were determined. Results show that alkyl polyglucosides, at the standard initial concentration of 100 mgC L(-1), are not completely biodegradable in anaerobic conditions because they inhibit the biogas production. The alkyl polyglucoside having the shortest alkyl chain showed the fastest biodegradability and reached the higher percentage of final mineralization. The anaerobic process was well adjusted to a pseudo first-order equation using the carbon produced as gas during the test; also, kinetics parameters and a global rate constant for all the involved metabolic process were determined. This modeling is helpful to evaluate the biodegradation or the persistence of alkyl polyglucosides under anaerobic conditions in the environment and in the wastewater treatment.

  15. Coupled Transport of PAH and Surfactants in Natural Aquifer Material

    Science.gov (United States)

    Danzer, J.; Grathwohl, P.

    1998-03-01

    Surfactants in aqueous solution adsorb onto mineral surfaces and form micelles above the critical micelle concentration (CMC) due to their physico-chemical properties. Hydrophobic organic compounds such as polycyclic aromatic hydrocarbons (PAHs) have a high affinity for the adsorbed surfactant layers (monomers, hemimicelles and admicelles) and to the micelles in the mobile aqueous phase. The transport of PAHs is controlled by the concentration of the surfactant and the partition coefficients, of the PAHs between water and admicelles (adsolubilization: K adm) and water and micelles (solubilization: K mic), respectively. These partition coefficients were measured in laboratory batch and column experiments using phenanthrene as a chemical probe for the PAHs, a non-ionic surfactant (Terrasurf G50), natural aquifer sand (River Neckar Alluvium: RNA) and its petrographic subcomponents. The sorption of the surfactant can be described by a linear isotherm for concentrations below the CMC and a sorption maximum above the CMC, which both depend on the grain size and the surfactant accessible internal surface area of the particles. K adm was found to be higher than K mic. Both depend on the surfactant's properties, such as alkyl chain length, polar headgroup or ethoxylation. In column experiments an increasing retardation of phenanthrene was observed up to the CMC followed by a facilitated transport at surfactant concentration several times the CMC.

  16. Adsorption at air-water and oil-water interfaces and self-assembly in aqueous solution of ethoxylated polysorbate nonionic surfactants.

    Science.gov (United States)

    Penfold, Jeffrey; Thomas, Robert K; Li, Peixun X; Petkov, Jordan T; Tucker, Ian; Webster, John R P; Terry, Ann E

    2015-03-17

    The Tween nonionic surfactants are ethoxylated sorbitan esters, which have 20 ethylene oxide groups attached to the sorbitan headgroup and a single alkyl chain, lauryl, palmityl, stearyl, or oleyl. They are an important class of surfactants that are extensively used in emulsion and foam stabilization and in applications associated with foods, cosmetics and pharmaceuticals. A range of ethoxylated polysorbate surfactants, with differing degrees of ethoxylation from 3 to 50 ethylene oxide groups, have been synthesized and characterized by neutron reflection, small-angle neutron scattering, and surface tension. In conjunction with different alkyl chain groups, this provides the opportunity to modify their surface properties, their self-assembly in solution, and their interaction with macromolecules, such as proteins. Adsorption at the air-water and oil-water interfaces and solution self-assembly of the range of ethoxylated polysorbate surfactants synthesized are presented and discussed.

  17. A comparison of the solvation structure and dynamics of the lithium ion in linear organic carbonates with different alkyl chain lengths.

    Science.gov (United States)

    Fulfer, K D; Kuroda, D G

    2017-09-20

    The structure and dynamics of electrolytes composed of lithium hexafluorophosphate (LiPF6) in dimethyl carbonate, ethyl methyl carbonate, and diethyl carbonate were investigated using a combination of linear and two-dimensional infrared spectroscopies. The solutions studied here have a LiPF6 concentration of X(LiPF6) = 0.09, which is typically found in commercial lithium ion batteries. This study focuses on comparing the differences in the solvation shell structure and dynamics produced by linear organic carbonates of different alkyl chain lengths. The IR experiments show that either linear carbonate forms a tetrahedral solvation shell (coordination number of 4) around the lithium ion irrespective of whether the solvation shell has anions in close proximity to the carbonates. Moreover, analysis of the absorption cross sections via FTIR and DFT computations reveals a distortion in the angle formed by Li(+)-O[double bond, length as m-dash]C which decreases from the expected 180° when the alkyl chains of the carbonate are lengthened. In addition, our findings also reveal that, likely due to its asymmetric structure, ethyl methyl carbonate has a significantly more distorted tetrahedral lithium ion solvation shell than either of the other two investigated carbonates. IR photon echo studies further demonstrate that the motions of the solvation shell have a time scale of a few picoseconds for all three linear carbonates. Interestingly, a slowdown of the in place-motions of the first solvation shell is observed when the carbonate has a longer alkyl chain length irrespective of the symmetry. In addition, vibrational energy transfer with a time scale of tens of picoseconds is observed between strongly coupled modes arising from the solvation shell structure of the Li(+) which corroborates the modeling of these solvation shells in terms of highly coupled vibrational states. Results of this study provide new insights into the molecular structure and dynamics of the lithium

  18. Diacyltransferase Activity and Chain Length Specificity of Mycobacterium tuberculosis PapA5 in the Synthesis of Alkyl β-Diol Lipids.

    Science.gov (United States)

    Touchette, Megan H; Bommineni, Gopal R; Delle Bovi, Richard J; Gadbery, John E; Nicora, Carrie D; Shukla, Anil K; Kyle, Jennifer E; Metz, Thomas O; Martin, Dwight W; Sampson, Nicole S; Miller, W Todd; Tonge, Peter J; Seeliger, Jessica C

    2015-09-08

    Although they are classified as Gram-positive bacteria, Corynebacterineae possess an asymmetric outer membrane that imparts structural and thereby physiological similarity to more distantly related Gram-negative bacteria. Like lipopolysaccharide in Gram-negative bacteria, lipids in the outer membrane of Corynebacterineae have been associated with the virulence of pathogenic species such as Mycobacterium tuberculosis (Mtb). For example, Mtb strains that lack long, branched-chain alkyl esters known as dimycocerosates (DIMs) are significantly attenuated in model infections. The resultant interest in the biosynthetic pathway of these unusual virulence factors has led to the elucidation of many of the steps leading to the final esterification of the alkyl β-diol, phthiocerol, with branched-chain fatty acids known as mycocerosates. PapA5 is an acyltransferase implicated in these final reactions. Here, we show that PapA5 is indeed the terminal enzyme in DIM biosynthesis by demonstrating its dual esterification activity and chain-length preference using synthetic alkyl β-diol substrate analogues. By applying these analogues to a series of PapA5 mutants, we also revise a model for the substrate binding within PapA5. Finally, we demonstrate that the Mtb Ser/Thr kinases PknB and PknE modify PapA5 on three overlapping Thr residues and that a fourth Thr is unique to PknE phosphorylation. These results clarify the DIM biosynthetic pathway and indicate post-translational modifications that warrant further elucidation for their roles in the regulation of DIM biosynthesis.

  19. Time-Resolved EPR Study of Electron-Hole Dissociations Influenced by Alkyl Side Chains at the Photovoltaic Polyalkylthiophene:PCBM Interface.

    Science.gov (United States)

    Miura, Taku; Aikawa, Motoko; Kobori, Yasuhiro

    2014-01-02

    Nanosecond time-resolved electron paramagnetic resonance (TREPR) spectroscopy has been utilized at T = 77 K to characterize alkyl side-chain effects on geometries and on the electronic couplings (VCR) of transient charge-separated (CS) states in the photoactive layers fabricated by the spin-coating of mixed solutions of regioregular polyalkylthiophenes (RR-P3AT) and [6,6]-C61-butyric acid methyl ester (PCBM). By increasing the alkyl side-chain number from 6 to 12 in P3AT, a highly distant and long-lived CS state has been obtained. This result is explained by a coupling of the hole dissociation to the polymer librations by the side-chains. From an exponential decay of VCR with respect to the CS distance, the attenuation factor (βe) has been determined to be βe = 0.2 Å(-1). Such a long-range tunneling feature is explained by the generations of the shallowly trapped, delocalized electron-hole pairs by the dissociation of the hole toward π-stacking directions at the organic photovoltaic interface.

  20. Study of conformation and dynamic of surfactant molecules in graphite oxide via NMR

    Energy Technology Data Exchange (ETDEWEB)

    Ai, X.Q. [Jiangsu Second Normal University, College of Physics and Electronic Engineering, Nanjing (China); Ma, L.G. [Nanjing Xiaozhuang University, School of Electronic Engineering, Nanjing (China)

    2016-08-15

    The conformation and dynamic of surfactant in graphite oxide (GO) was investigated by solid-state {sup 13}C magic-angle-spinning NMR and {sup 1}H-{sup 13}C cross-polarization/magic-angle-spinning NMR spectra. The conformation ordering of the alkyl chains in the confined system shows strong dependence on its orientation. While the alkyl chains parallel to the GO layer in lateral monolayer arrangement are in gauche conformation in addition to a small amount of all-trans conformation, those with orientation radiating away from the GO in paraffin bilayer arrangement is in all-trans conformation in addition to some gauche conformation even though high-order diffraction peaks appears. NMR results suggest that the least mobile segment is located at the GO-surfactant interface corresponding to the N-methylene group. Further from it, the mobility of the alkyl chain increases. The terminal methyl and N-methyl carbon groups have the highest mobile. The chains in all-trans conformational state are characterized as more rigid than chains with gauche conformation; each segment of the confined alkyl chains with the lateral monolayer arrangement exhibits less mobility as compared to that with the paraffin bilayer arrangement. (orig.)

  1. Effects of waste activated sludge and surfactant addition on primary sludge hydrolysis and short-chain fatty acids accumulation.

    Science.gov (United States)

    Ji, Zhouying; Chen, Guanlan; Chen, Yinguang

    2010-05-01

    This paper focused on the effects of waste activated sludge (WAS) and surfactant sodium dodecylbenzene sulfonate (SDBS) addition on primary sludge (PS) hydrolysis and short-chain fatty acids (SCFA) accumulation in fermentation. The results showed that sludge hydrolysis, SCFA accumulation, NH(4)(+)-N and PO(4)(3-)-P release, and volatile suspended solids (VSS) reduction were increased by WAS addition to PS, which were further increased by the addition of SDBS to the mixture of PS and WAS. Acetic, propionic and valeric acids were the top three SCFA in all experiments. Also, the fermentation liquids of PS, PS+WAS, and PS+WAS+SDBS were added, respectively, to municipal wastewater to examine their effects on biological municipal wastewater treatment, and the enhancement of both wastewater nitrogen and phosphorus removals was observed compared with no fermentation liquid addition.

  2. Low-band-gap conjugated polymers of dithieno[2,3-b:7,6-b]carbazole and diketopyrrolopyrrole: effect of the alkyl side chain on photovoltaic properties.

    Science.gov (United States)

    Deng, Yunfeng; Chen, Yagang; Liu, Jian; Liu, Lihui; Tian, Hongkun; Xie, Zhiyuan; Geng, Yanhou; Wang, Fosong

    2013-06-26

    Four donor–acceptor (D–A) conjugated polymers of dithieno[2,3-b;7,6-b]carbazole (DTC) and diketopyrrolopyrrole, which have different alkyls on the nitrogen atom in the DTC unit and are named as P-C8C8, P-C5C5, P-C12, and P-C10, respectively, have been synthesized for studying the effect of the alkyl side chains on the optoelectronic properties of the polymers. All polymers are soluble in various organic solvents and exhibit identical optical band gaps (E(g)(opt)) of ~1.3 eV and highest occupied molecular orbital energy levels of ~−5.1 eV. Organic thin-film transistors and bulk heterojunction polymer solar cells (BHJ PSCs) with phenyl-C(71)-butyric acid methyl ester (PC(71)BM) as the electron-accepting material were fabricated via solution spin-casting. Compared to the polymers substituted by branched alkyl chains, the polymers with straight alkyl chains show higher hole mobility. Of these polymers, P-C10 exhibits the highest field effect mobility up to 0.011 cm(2)/V·s. The alkyl chain on the DTC unit has a strong impact on the film morphology of polymer:PC(71)BM blends. Severe phase separation was found for polymers containing branched alkyl chains, and those with straight alkyl chains formed uniform films featuring fine phase separation. An open-circuit voltage (V(oc)) of 0.72 V, a short-circuit current density (J(sc)) of 13.4 mA/cm(2), a fill factor (FF) of 62%, and a power conversion efficiency (PCE) of 5.9% were demonstrated for BHJ PSCs based on the P-C10:PC(71)BM [1:3 (w/w)] blend film.

  3. Application of alkyl polyglycoside surfactant in ultrasonic-assisted extraction followed by macroporous resin enrichment for the separation of vitexin-2″-O-rhamnoside and vitexin from Crataegus pinnatifida leaves.

    Science.gov (United States)

    Han, Feng; Guo, Yupin; Gu, Huiyan; Li, Fenglan; Hu, Baozhong; Yang, Lei

    2016-02-15

    An alkyl polyglycoside (APG) surfactant was used in ultrasonic-assisted extraction to effectively extract vitexin-2″-O-rhamnoside (VOR) and vitexin (VIT) from Crataegus pinnatifida leaves. APG0810 was selected as the surfactant. The extraction process was optimized for ultrasonic power, the APG concentration, ultrasonic time, soaking time, and liquid-solid ratio. The proposed approach showed good recovery (99.80-102.50% for VOR and 98.83-103.19% for VIT) and reproducibility (relative standard deviation, n=5; 3.7% for VOR and 4.2% for VIT) for both components. The proposed sample preparation method is both simple and effective. The use of APG for extraction of key herbal ingredients shows great potential. Ten widely used commercial macroporous resins were evaluated in a screening study to identify a suitable resin for the separation and purification of VOR and VIT. After comparing static and dynamic adsorption and desorption processes, HPD100B was selected as the most suitable resin. After column adsorption and desorption on this resin, the target compounds VOR and VIT can be effectively separated from the APG0810 extraction solution. Recoveries of VOR and VIT were 89.27%±0.42% and 85.29%±0.36%, respectively. The purity of VOR increased from 35.0% to 58.3% and the purity of VIT increased from 12.5% to 19.9%. Copyright © 2016 Elsevier B.V. All rights reserved.

  4. Phosphine oxide surfactants revisited.

    Science.gov (United States)

    Stubenrauch, Cosima; Preisig, Natalie; Laughlin, Robert G

    2016-04-01

    This review summarizes everything we currently know about the nonionic surfactants alkyl dimethyl (C(n)DMPO) and alkyl diethyl (C(n)DEPO) phosphine oxide (PO surfactants). The review starts with the synthesis and the general properties (Section 2) of these compounds and continues with their interfacial properties (Section 3) such as surface tension, surface rheology, interfacial tension and adsorption at solid surfaces. We discuss studies on thin liquid films and foams stabilized by PO surfactants (Section 4) as well as studies on their self-assembly into lyotropic liquid crystals and microemulsions, respectively (Section 5). We aim at encouraging colleagues from both academia and industry to take on board PO surfactants whenever possible and feasible because of their broad variety of excellent properties.

  5. [Dental plaque microcosm biofilm behavior on a resin composite incorporated with nano-antibacterial inorganic filler containing long-chain alkyl quaternary ammonium salt].

    Science.gov (United States)

    Junling, Wu; Qiang, Zhang; Ruinan, Sun; Ting, Zhu; Jianhua, Ge; Chuanjian, Zhou

    2015-12-01

    To develop a resin composite incorporated with nano-antibacterial inorganic filler containing long-chain alkyl quaternary ammonium salt, and to measure its effect on human dental plaque microcosm biofilm. A novel nano-antibacterial inorganic filler containing long-chain alkyl quaternary ammonium salt was synthesized according to methods introduced in previous research. Samples of the novel nano-antibacterial inorganic fillers were modified by a coupling agent and then added into resin composite at 0%, 5%, 10%, 15% or 20% mass fractions; 0% composite was used as control. A flexural test was used to measure resin composite mechanical properties. Results showed that a dental plaque microcosm biofilm model with human saliva as inoculum was formed. Colony-forming unit (CFU) counts, lactic acid production, and live/dead assay of biofilm on the resin composite were calculated to test the effect of the resin composite on human dental plaque microcosm biofilm. The incorporation of nano-antibacterial inorganic fillers with as much as 15% concentration into the resin composite showed no adverse effect on the mechanical properties of the resin composite (P > 0.05). Resin composite containing 5% or more nano-antibacterial inorganic fillers significantly inhibited the metabolic activity of dental plaque microcosm biofilm, suggesting its strong antibacterial potency (P resin composite exhibited a strong antibacterial property upon the addition of up to 5% nano-antibacterial inorganic fillers, thereby leading to effective caries inhibition in dental application.

  6. Thermodynamics of micellization of nonionic saccharide-based N-acyl-N-alkylaldosylamine and N-acyl-N-alkylamino-1-deoxyalditol surfactants

    NARCIS (Netherlands)

    Pestman, J.M.; Kevelam, J.; Blandamer, M.J.; Doren, H.A. van; Kellogg, R.M.; Engberts, J.B.F.N.

    1999-01-01

    Eight homologous series of nonionic carbohydrate-derived surfactants in which the alkyl chains are linked through N-acylated amine bonds were synthesized, and their critical micelle concentrations (cmc's) and standard enthalpies of micellization were determined using titration microcalorimetry. Gibb

  7. Structural properties of the active layer of discotic hexabenzocoronene/perylene diimide bulk hetero junction photovoltaic devices: The role of alkyl side chain length

    Energy Technology Data Exchange (ETDEWEB)

    Al-Hussein, M., E-mail: m.alhussein@ju.edu.jo [Department of Physics, University of Jordan, Amman 11942 (Jordan); Hesse, H.C.; Weickert, J. [Ludwig-Maximilians-University Munich, Department of Physics and Center for NanoScience(CeNS), Amalienstr.54, 80799 Munich (Germany); Doessel, L.; Feng, X.; Muellen, K. [Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz (Germany); Schmidt-Mende, L. [Ludwig-Maximilians-University Munich, Department of Physics and Center for NanoScience(CeNS), Amalienstr.54, 80799 Munich (Germany)

    2011-10-31

    We investigate thin blend films of phenyl-substituted hexa-peri-hexabenzocoronenes (HBC) with various alkyl side chain lengths ((CH{sub 2})n, n = 6, 8, 12 and 16)/perylenediimide (PDI). These blends constitute the active layers in bulk-hetero junction organic solar cells we studied recently [1]. Their structural properties are studied by both scanning electron microscopy and X-ray diffraction measurements. The results support the evidence for the formation of HBC donor-PDI acceptor complexes in all blends regardless of the side chain length of the HBC molecule. These complexes are packed into a layered structure parallel to the substrate for short side chain HBC molecules (n = 6 and 8). The layered structure is disrupted by increasing the side chain length of the HBC molecule and eventually a disordered structure is formed for long side chains (n > 12). We attribute this behavior to the size difference between the aromatic parts of the HBC and PDI molecules. For short side chains, the size difference results in a room for the side chains of the two molecules to fill in the space around the aromatic cores. For long side chains (n > 12), the empty space will not be enough to accommodate this increase, leading to the disruption of the layered structure and a rather disordered structure is formed. Our results highlight the importance of the donor-acceptor interaction in a bulk heterojunction active layer as well as the geometry of the two molecules and their role in determining the structure of the active layer and thus their photovoltaic performance.

  8. pH-Sensitive surfactants from lysine: assessment of their cytotoxicity and environmental behavior.

    Science.gov (United States)

    Colomer, Aurora; Pinazo, Aurora; García, Maria Teresa; Mitjans, Montserrat; Vinardell, M Pilar; Infante, Maria Rosa; Martínez, Verónica; Pérez, Lourdes

    2012-04-10

    The toxicity and environmental behavior of new pH-sensitive surfactants from lysine are presented. Three different chemical structures are studied: surfactants with one amino acid and one alkyl chain, surfactants with two amino acids on the polar head and one alkyl chain, and gemini surfactants. The pH sensitivity of these compounds can be tuned by modifying their chemical structures. Cytotoxicity has been evaluated using erythrocytes and fibroblast cells. The toxic effects against these cells depend on the hydrophobicity of the molecules as well as their cationic charge density. The effect of hydrophobicity and cationic charge density on toxicity is different for each type of cells. For erythrocytes, the toxicity increases as hydrophobicity and charge density increases. Nevertheless, for fibroblasts cationic charge density affects cytotoxicity in the opposite way: the higher charge density, the lower the toxicity. The effect of the pH on hemolysis has been evaluated in detail. The aquatic toxicity was established using Daphnia magna . All surfactants yielded EC(50) values considerably higher than that reported for cationic surfactants based on quaternary ammonium groups. Finally, their biodegradability was evaluated using the CO(2) headspace test (ISO 14593). These lysine derivatives showed high levels of biodegradation under aerobic conditions and can be classified as "readily biodegradable compounds".

  9. Polycondensation of dicarboxylic acids and diols in water catalyzed by surfactant-combined catalysts and successive chain extension.

    Science.gov (United States)

    Takasu, Akinori; Takemoto, Aki; Hirabayashi, Tadamichi

    2006-01-01

    Direct dehydration polycondensation of dicarboxylic acids and alcohols was carried out by surfactant-combined Brønsted and Lewis acids. This procedure did not require the removal of water, because the esterification was established at the interface of the emulsion in water. Emulsion polycondensations of 1,9-nonanediol (1,9-ND) and dodecanedioic acid (DDA) (the molar ratio of dicarboxylic acid to diol = 1:1) were carried out at 80 degrees C for 48 h in the presence of 16 wt % DBSA. The corresponding polyester (M(w) = 10.1 x 10(3)) was obtained in an excellent yield (99%). Chain extension in the emulsion was carried out using hexamethylene diisocyanate as the chain extender. SEC measurements indicated the expected shift to higher molecular weight region (M(w) = 11.4 x 10(3), M(w)/M(n) = 3.4) compared with parent polyester (M(w) = 4.5 x 10(3), M(w)/M(n) = 2.2).

  10. Measurement of cytotoxicity and irritancy potential of sugar-based surfactants on skin-related 3D models.

    Science.gov (United States)

    Lu, Biao; Miao, Yong; Vigneron, Pascale; Chagnault, Vincent; Grand, Eric; Wadouachi, Anne; Postel, Denis; Pezron, Isabelle; Egles, Christophe; Vayssade, Muriel

    2017-04-01

    Sugar-based surfactants present surface-active properties and relatively low cytotoxicity. They are often considered as safe alternatives to currently used surfactants in cosmetic industries. In this study, four sugar-based surfactants, each with an eight carbon alkyl chain bound to a glucose or a maltose headgroup through an amide linkage, were synthesized and compared to two standard surfactants. The cytotoxic and irritant effects of surfactants were evaluated using two biologically relevant models: 3D dermal model (mouse fibroblasts embedded in collagen gel) and reconstituted human epidermis (RHE, multi-layered human keratinocytes). Results show that three synthesized surfactants possess lower cytotoxicity compared to standard surfactants as demonstrated in the 3D dermal model. Moreover, the IC50s of surfactants against the 3D dermal model are higher than IC50s obtained with the 2D dermal model (monolayer mouse fibroblasts). Both synthesized and standard surfactants show no irritant effects after 48h of topical application on RHE. Throughout the study, we demonstrate the difficulty to link the physico-chemical properties of surfactants and their cytotoxicity in complex models. More importantly, our data suggest that, prior to in vivo tests, a complete understanding of surfactant cytotoxicity or irritancy potential requires a combination of cellular and tissue models. Copyright © 2017 Elsevier Ltd. All rights reserved.

  11. Hierarchical control of porous silica by pH adjustment: Alkyl polyamines as surfactants for bimodal silica synthesis and its carbon replica

    Science.gov (United States)

    Abellán, G.; Carrillo, A. I.; Linares, N.; Serrano, E.; García-Martínez, J.

    2009-08-01

    Bimodal macro-mesoporous silica networks have been prepared in a simple one-pot synthesis using an inexpensive tetramine surfactant and tetraethoxysilane as a silica precursor. These novel materials show high pore volumes and templated mesopores (average pore size 3.0 nm) embedded in 20 nm thick walls forming interparticle large meso/macropores. The judicious control of the pH during the silica formation allows for the precise control of the interparticle condensation, likely due to the change in the interaction between the tetramine surfactant and the silica precursors. Finally, a highly porous carbon replica with bimodal porosity was prepared by using the bimodal silica as a hard sacrificial template. The microstructure of the silica template was accurately transferred to the carbon material obtaining high surface areas (up to 1300 m 2 g -1) and total pore volumes ≥2 cm 3 g -1.

  12. Interactions of /sup 14/N:/sup 15/N stearic acid spin-label pairs: effects of host lipid alkyl chain length and unsaturation

    Energy Technology Data Exchange (ETDEWEB)

    Feix, J.B.; Yin, J.J.; Hyde, J.S.

    1987-06-30

    Electron-electron double resonance (ELDOR) and saturation recovery electron paramagnetic resonance (EPR) spectroscopy have been employed to examine the interactions of /sup 14/N:/sup 15/N stearic acid spin-label pairs in fluid-phase model membrane bilayers composed of a variety of phospholipids. The (/sup 14/N)-16-doxylstearate:(/sup 15/N)-16-doxylstearate (16:16) pair was utilized to measure lateral diffusion of the spin-labels, while the (/sup 14/N)-16-doxylstearate:(/sup 15/N)-5-doxylstearate (16:5) pair provided information on vertical fluctuations of the 16-doxylstearate nitroxide moiety toward the membrane surface. Three saturated host lipids of varying alkyl chain length (dimyristoylphosphatidylcholine (DMPC), dipalmitoylphosphatidylcholine (DPPC), and distearoylphosphatidylcholine (DSPC)), an ..cap alpha..-saturated, ..beta..-unsaturated lipid (1-palmitoyl-2-oleoylphosphatidylcholine (POPC)), and phosphatidylcholine from a natural source (egg yolk phosphatidylcholine (egg PC)) were utilized as host lipids. Lateral diffusion of the stearic acid spin-labels was only slightly affected by alkyl chain length at a given reduced temperature (T/sub r/) in the saturated host lipids but was significantly decreased in POPC at the same T/sub r/. Lateral diffusion in DMPC, POPC, and egg PC was quite similar at 37/sup 0/C. A strong correlation was noted between lateral diffusion constants and rotational mobility of (/sup 14/N)-16-doxylstearate. Vertical fluctuations were likewise only slightly influenced by alklyl chain length but were strongly diminished in POPC and egg PC relative to the saturated systems. This diminution of the 16:5 interaction was observed even under conditions where no differences were discernible by conventional EPR.

  13. Liposome encapsulation of lipophilic N-alkyl-propanediamine platinum complexes: impact on their cytotoxic activity and influence of the carbon chain length

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Heveline; Fontes, Ana Paula S. [Universidade Federal de Juiz de Fora (UFJF), MG (Brazil). Dept. de Quimica; Lopes, Miriam Teresa P. [Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG (Brazil). Dept. de Farmacologia; Frezard, Frederic, E-mail: frezard@icb.ufmg.b [Universidade Federal de Minas Gerais (UFMG), Belo Horizonte, MG (Brazil). Dept. de Fisiologia e Biofisica

    2010-07-01

    Antitumor platinum(II) complexes derived from N-alkyl-propanediamine differing in the length of their carbon chain (C8, C10, C12 and C14) were incorporated in liposomes and the cytotoxic activity of these formulations was evaluated against tumor (A{sub 549}, MDA-MB-231, B16-F1 and B16-F10) and non-tumor (BHK-21 and CHO) cell lines. Stable and monodisperse liposome suspensions incorporating the platinum complexes were obtained from the lipid composition consisting of distearoyl-sn-glycero-3-phosphocholine, cholesterol and 1,2-distearoyl-sn-glycero- 3-phosphoethanolamine-N-(methoxy(polyethylene glycol)-2000) at 5:3:0.3 molar ratio. The entrapment efficiency (EE%) of the platinum complexes in liposomes increased with the carbon chain length. EE% was higher than 80% in C12- and C14-derivatives. The effect of liposome encapsulation on the cytotoxic activity of the complexes was found to depend on the carbon chain length. These data indicate that the highest drug bioavailability from liposome formulations was achieved with the complex showing intermediate carbon chain length and partition between the liposome membrane and aqueous phase. (author)

  14. Production of long chain alkyl esters from carbon dioxide and electricity by a two-stage bacterial process

    DEFF Research Database (Denmark)

    Lehtinen, Tapio; Efimova, Elena; Tremblay, Pier-Luc

    2017-01-01

    Microbial electrosynthesis (MES) is a promising technology for the reduction of carbon dioxide into value-added multicarbon molecules. In order to broaden the product profile of MES processes, we developed a two-stage process for microbial conversion of carbon dioxide and electricity into long...... in an aerobic bioprocess. In this proof-of-principle study, we demonstrate for the first time the bacterial production of long alkyl esters (wax esters) from carbon dioxide and electricity as the sole sources of carbon and energy. The process holds potential for the efficient production of carbon...

  15. Thermodynamics of micellization of cationic surfactants based on O-alkyl and O-perfluoro-N,N'-diisopropylisourea: Effect of the counter ion nature

    Energy Technology Data Exchange (ETDEWEB)

    Lehanine, Zineb, E-mail: zlehanine@usthb.dz [Laboratoire de Synthese Organique, Faculte de chimie, U.S.T.H.B., B.P. 32, El Alia 16111, Bab Ezzouar, Alger (Algeria); Badache, Leila [Laboratoire de Synthese Organique, Faculte de chimie, U.S.T.H.B., B.P. 32, El Alia 16111, Bab Ezzouar, Alger (Algeria)

    2011-09-15

    Graphical abstract: The pseudo phase thermodynamic model was applied to study the process of micellization of O-dodecyl- and O-tridecafluorooctyl-N,N'-diisopropylisourea hydrohalogenides. Free energy of micellization is weakly temperature dependent and decreased slightly with the size of the counterion, indicating a more favored micellization. Enthalpies and entropies of micellization decrease strongly with increasing temperature. The enthalpy-entropy compensation phenomenon was observed for all the surfactants studied. Highlights: > The pseudo phase thermodynamic model was applied to study the process of micellization of O-dodecyl- and O-tridecafluorooctyl-N,N'-diisopropylisourea hydrohalogenides. > Free energy of micellization is weakly temperature dependent and decreased slightly with the size of the counterion, indicating a more favored micellization. > Enthalpies and entropies of micellization decrease strongly with increasing temperature. > The enthalpy-entropy compensation phenomenon was observed for all the surfactants studied. - Abstract: A thermodynamic study on the micellization process of two series of cationic surfactants, viz. the O-dodecyl-N,N'-diisopropylisourea hydrochloride, hydrobromide, and hydroiodide and the O-tridecafluorooctyl-N,N'-diisopropylisourea hydrochloride, and hydrobromide, is reported. In order to explain the effect of the counter ion nature in the micellization process, thermodynamic parameters to include the standard free energy ({Delta}G{sub mic}{sup 0}), enthalpy ({Delta}H{sub mic}{sup 0}), entropy ({Delta}S{sub mic}{sup 0}), and heat capacity ({Delta}C{sub p,mic}{sup 0}) of micellization have been discussed. These parameters are evaluated from the variation of the critical micelle concentration (CMC) with temperature by fitting these values to expressions derived on the basis of a micellization thermodynamic model. The heat capacities of micellization ({Delta}C{sub p,mic}{sup 0}) were determined from the

  16. Effect of Structure on Transport Properties (Viscosity, Ionic Conductivity, and Self-Diffusion Coefficient) of Aprotic Heterocyclic Anion (AHA) Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in the Phosphonium Cation.

    Science.gov (United States)

    Sun, Liyuan; Morales-Collazo, Oscar; Xia, Han; Brennecke, Joan F

    2016-06-30

    A series of room-temperature ionic liquids (ILs) composed of triethyl(alkyl)phosphonium cations paired with three different aprotic heterocyclic anions (AHAs) (alkyl = butyl ([P2224](+)) and octyl ([P2228](+))) were prepared to investigate the effect of cationic alkyl chain length on transport properties. The transport properties and density of these ILs were measured from 283.15 to 343.15 K at ambient pressure. The dependence of the transport properties (viscosity, ionic conductivity, diffusivity, and molar conductivity) on temperature can be described by the Vogel-Fulcher-Tamman (VFT) equation. The ratio of the molar conductivity obtained from the molar concentration and ionic conductivity measurements to that calculated from self-diffusion coefficients (measured by pulsed gradient spin-echo nuclear magnetic resonance spectroscopy) using the Nernst-Einstein equation was used to quantify the ionicity of these ILs. The molar conductivity ratio decreases with increasing number of carbon atoms in the alkyl chain, indicating that the reduced Coulombic interactions resulting from lower density are more than balanced by the increased van der Waals interactions between the alkyl chains. The results of this study may provide insight into the design of ILs with enhanced dynamics that may be suitable as electrolytes in lithium ion batteries and other electrochemical applications.

  17. Effects of imidazolium-based ionic surfactants on the size and dynamics of phosphatidylcholine bilayers with saturated and unsaturated chains.

    Science.gov (United States)

    Lee, Hwankyu

    2015-07-01

    Imidazolium-based ionic surfactants of different sizes were simulated with 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) bilayers. Regardless of the phospholipid type, larger surfactants at higher concentrations more significantly insert into the bilayer and increase the bilayer-surface size, in agreement with experiments and previous simulations. Insertion of surfactants only slightly decreases the bilayer thickness, as also observed in experiments. Although the surfactant insertion and its effect on the bilayer size and thickness are similar in different types of bilayers, the volume fractions of surfactants in the bilayer are higher for DMPC bilayers than for POPC and DOPC bilayers. In particular, ionic surfactants with four hydrocarbons yield their volume fractions of 4.6% and 8.7%, respectively, in POPC and DMPC bilayers, in quantitative agreement with experimental values of ∼5% and ∼10%. Also, the inserted surfactants increase the lateral diffusivity of the bilayer, which depends on the bilayer type. These findings indicate that although the surfactant insertion does not depend on the bilayer type, the effects of surfactants on the volume fraction and bilayer dynamics occur more significantly in the DMPC bilayer because of the smaller area per lipid and shorter saturated tails, which helps explain the experimental observations regarding different volume fractions of surfactants in POPC and DMPC bilayers.

  18. Adsorptive removal of naphthalene induced by structurally different Gemini surfactants in a soil-water system.

    Science.gov (United States)

    Wei, Jia; Li, Jun; Huang, Guohe; Wang, Xiujie; Chen, Guanghui; Zhao, Baihang

    2016-09-01

    A new generation of surfactant, Gemini surfactants, have been synthesized and have attracted the attention of various industrial and academic research groups. This study focused on the use of symmetric and dissymmetric quaternary ammonium Gemini surfactants to immobilize naphthalene onto soil particles, and is used as an example of an innovative application to remove HOC in situ using the surfactant-enhanced sorption zone. The sorption capacity of modified soils by Gemini surfactant and natural soils was compared and the naphthalene sorption efficiency, in the absence and presence of Gemini surfactants with different alkyl chain lengths, was investigated in the soil-water system. The results have shown that the increased added Gemini surfactant formed admicelles at the interface of soil/water having superior capability to retard contaminant. Symmetric and dissymmetric Gemini surfactants have opposite effect on the aspect of removing of PAH attributing to their solubilization and sorption behavior in soil-water system. Compared with the natural soil, sorption of naphthalene by Gemini-modified soil is noticeably enhanced following the order of C12-2-16 < C12-2-12 < C12-2-8. However, the symmetric Gemini surfactant C12-2-12 is the optimized one for in situ barrier remediation, which is not only has relative high retention ability but also low dosage.

  19. Molecular and crystalline structures of three (S)-4-alkoxycarbonyl-2-azetidinones containing long alkyl side chains from synchrotron X-ray powder diffraction data.

    Science.gov (United States)

    Seijas, Luis E; Mora, Asiloé J; Delgado, Gerzon E; López-Carrasquero, Francisco; Báez, María E; Brunelli, Michela; Fitch, Andrew N

    2009-12-01

    The (S)-4-alkoxo-2-azetidinecarboxylic acids are optically active beta-lactam derivatives of aspartic acid, which are used as precursors of carbapenem-type antibiotics and poly-beta-aspartates. The crystal structures of three (S)-4-alkoxo-2-azetidinecarboxylic acids with alkyl chains with 10, 12 and 16 C atoms were solved using parallel tempering and refined against the X-ray powder diffraction data using the Rietveld method. The azetidinone rings in the three compounds display a pattern of asymmetrical bond distances and an almost planar conformation; these characteristics are compared with periodic solid-state, gas-phase density-functional theory (DFT) calculations and MOGUL average bond distances and angles from the CSD. The compounds pack along [001] as corrugated sheets separated by approximately 4.40 A and connected by hydrogen bonds of the type N-H...O.

  20. DNA association-enhanced physical stability of catanionic vesicles composed of ion pair amphiphile with double-chain cationic surfactant.

    Science.gov (United States)

    Lee, Jung; Chang, Chien-Hsiang

    2014-09-01

    Physical stability control of vesicle/DNA complexes is a key issue for the development of catanionic vesicles composed of ion pair amphiphile (IPA) as DNA carriers. In this work, physical stability characteristics of the complexes of DNA with positively charged catanionic vesicles composed of an IPA and a double-chain cationic surfactant, dihexadecyldimethylammonium bromide (DHDAB), were explored. It was found that in water, the mixed IPA/DHDAB catanionic vesicles became stable when the mole fraction of DHDAB (xDHDAB) was increased up to 0.5. The improved physical stability of the vesicles with a high xDHDAB could be related to the enhanced electrostatic interaction between the vesicles. When the catanionic vesicles interacted with DNA, excellent physical stability was detected for the vesicle/DNA complexes especially with a high xDHDAB. However, this could not be fully explained by the electrostatic interaction effect, and the role of molecular packing within the vesicular bilayers was apparently important. The corresponding Langmuir monolayer study demonstrated that the molecular packing of mixed IPA/DHDAB layers became ordered with DNA association due to inhibited desorption of the positively charged moiety of the IPA. Moreover, the DNA association-induced improvement in the molecular packing of the mixed IPA/DHDAB layers became pronounced with increased xDHDAB. The results imply that one can fabricate catanionic vesicle/DNA complexes with excellent physical stability through the improved molecular packing in the IPA vesicular bilayers with DHDAB addition and DNA association.

  1. Aerobic biodegradation of amphoteric amine-oxide-based surfactants: Effect of molecular structure, initial surfactant concentration and pH.

    Science.gov (United States)

    Ríos, Francisco; Lechuga, Manuela; Fernández-Serrano, Mercedes; Fernández-Arteaga, Alejandro

    2017-03-01

    The present study was designed to provide information regarding the effect of the molecular structure of amphoteric amine-oxide-based surfactants and the initial surfactant concentration on their ultimate biodegradation. Moreover, given this parameter's pH-dependence, the effect of pH was also investigated. Three amine-oxide-based surfactants with structural differences in their hydrophobic alkyl chain were tested: Lauramine oxide (AO-R12), Myristamine oxide (AO-R14) and Cocamidopropylamine oxide (AO-Cocoamido). We studied the ultimate biodegradation using the Modified OECD Screening Test at initial surfactant concentrations ranged from 5 to 75 mg L(-1) and at pH levels from 5 to 7.4. The results demonstrate that at pH 7.4, amine-oxide-based surfactants are readily biodegradable. In this study, we concluded that ω-oxidation can be assumed to be the main biodegradation pathway of amine-oxides and that differences in the biodegradability between them can be explained by the presence of an amide group in the alkyl chain of AO-Cocoamido; the CN fission of the amide group slows down their mineralization process. In addition, the increase in the concentration of the surfactant from 5 to 75 mg L(-1) resulted in an increase in the final biodegradation of AO-R12 and AO-R14. However, in the case of AO-Cocoamido, a clear relationship between the concentration and biodegradation cannot be stated. Conversely, the biodegradability of AO-R12 and AO-R14 was considerably lower in an acid condition than at a pH of 7.4, whereas AO-Cocoamido reached similar percentages in acid conditions and at a neutral pH. However, microorganisms required more time to acclimate.

  2. Synthesis and Solution Properties of Adamantane Containing Quaternary Ammonium Salt-type Cationic Surfactants: Hydrocarbon-based, Fluorocarbonbased and Bola-type.

    Science.gov (United States)

    Yoshimura, Tomokazu; Okada, Mari; Matsuoka, Keisuke

    2016-10-01

    Quaternary ammonium salt-type cationic surfactants with an adamantyl group (hydrocarbon-type; CnAdAB, fluorocarbon-type; Cm(F)C3AdAB, bola-type; Ad-s-Ad, where n, m and s represent hydrocarbon chain lengths of 8-16, fluorocarbon chain lengths of 4-8, and spacer chain length of 10-12) were synthesized via quaternization of N, N-dimethylaminoadamantane and n-alkyl bromide or 1, n-dibromoalkane. Conductivity and surface tension were measured to characterize the solution properties of the synthesized adamantyl group-containing cationic surfactants. In addition, the effects of hydrocarbon and fluorocarbon chain lengths and spacer chain length between headgroups on the measured properties were evaluated by comparison with those of conventional cationic surfactants. The critical micelle concentration (CMC) of CnAdAB and Ad-s-Ad was 2/5 of that for the corresponding conventional surfactants CnTAB and bola-type surfactants with similar number of carbons in the alkyl or alkylene chain; this was because of the increased hydrophobicity due to the adamantyl group. A linear relationship between the logarithm of CMC and the hydrocarbon chain length for CnAdAB was observed, as well as for CnTAB. The slope of the linear correlation for both surfactants was almost the same, indicating that the adamantyl group does not affect the CMC with variations in the hydrocarbon chain length. Similar to conventional surfactants CnTAB, the hydrocarbon-type CnAdAB is highly efficient in reducing the surface tension of water, despite the large occupied area per molecule resulting from the relatively bulky structure of the adamantane skeleton. On the other hand, the bola-type Ad-s-Ad resulted in increased surface tension compared to CnAdAB, indicating that the curved chain between adamantyl groups leads to poor adsorption and orientation at the air-water interface.

  3. Effect of side-chain asymmetry on the intermolecular structure and order-disorder transition in alkyl-substituted polyfluorenes

    DEFF Research Database (Denmark)

    Knaapila, Matti; Stepanyan, R.; Torkkeli, M.

    2016-01-01

    We study relations among the side-chain asymmetry, structure, and order-disorder transition (ODT) in hairy-rod-type poly(9,9-dihexylfluorene) (PF6) with two identical side chains and atactic poly(9-octyl-9-methyl-fluorene) (PF1-8) with two different side chains per repeat. PF6 and PF1-8 organize...... as an indistinguishable bilayer with a half thickness Hbilayer(PF1−8)/2≈H(PF6). The low grafting density region is structurally possible but not certain for PF6 and confirmed for PF1-8....

  4. Identification of alkyl dimethylbenzylammonium surfactants in water samples by solid-phase extraction followed by ion trap LC/MS and LC/MS/MS

    Science.gov (United States)

    Ferrer, I.; Furlong, E.T.

    2001-01-01

    A novel methodology was developed for the determination of alkyl (C12, C14, and C16) dimethylbenzylammonium chloride (benzalkonium chloride or BAC, Chemical Abstract Service number: 8001-54-5) in water samples. This method is based on solid-phase extraction (SPE) using polymeric cartridges, followed by high-performance liquid chromatography/ion trap mass spectrometry (LC/MS) and tandem mass spectrometry(MS/MS) detection, equipped with an electrospray interface in positive ion mode. Chromatographic separation was achieved for three BAC homologues by using a C18 column and a gradient of acetonitrile/10 millimolar aqueous ammonium formate. Total method recoveries were higher than 71% in different water matrices. The main ions observed by LC/MS were at mass-to-charge ratios (m/z) of 304, 332, and 360, which correspond to the molecular ions of the C12, C14, and C16 alkyl BAC, respectively. The unequivocal structural identification of these compounds in water samples was performed by LC/MS/MS after isolation and subsequent fragmentation of each molecular ion. The main fragmentation observed for the three different homologues corresponded to the loss of the toluyl group in the chemical structure, which leads to the fragment ions at m/z 212, 240, and 268 and a tropylium ion, characteristic of all homologues, at m/z 91. Detection limits for the methodology developed in this work were in the low nanogram-per-liter range. Concentration levels of BAC - ranging from 1.2 to 36.6 micrograms per liter - were found in surface-water samples collected downstream from different wastewater-treatment discharges, thus indicating its input and persistence through the wastewater-treatment process.

  5. Synthesis and bio-physicochemical properties of amide-functionalized N-methylpiperazinium surfactants.

    Science.gov (United States)

    Chauhan, Vinay; Singh, Sukhprit; Mishra, Rachana; Kaur, Gurcharan

    2014-12-15

    Four new amide functionalized N-methylpiperazinium amphiphiles having tetradecyl, hexadecyl alkyl chain lengths and counterions; chloride or bromide have been synthesized and characterized by various spectroscopic techniques. These new surfactants have been investigated in detail for their self-assembling behavior by surface tension, conductivity and fluorescence measurements. The thermodynamic parameters of these surfactants indicate that micellization is exothermic and entropy-driven. The dynamic light scattering (DLS) and transmission electron microscopy (TEM) experiments have been performed to insight the aggregate size of these cationics. Thermal degradation of these new surfactants has also been evaluated by thermal gravimetric analysis (TGA). These new surfactants form stable complexes with DNA as acknowledged by agarose gel electrophoresis, ethidium bromide exclusion and zeta potential measurements. They have also been found to have low cytotoxicity by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay on the C6 glioma cell line.

  6. Antibacterial Activity, in Vitro Cytotoxicity, and Cell Cycle Arrest of Gemini Quaternary Ammonium Surfactants.

    Science.gov (United States)

    Zhang, Shanshan; Ding, Shiping; Yu, Jing; Chen, Xuerui; Lei, Qunfang; Fang, Wenjun

    2015-11-10

    Twelve gemini quaternary ammonium surfactants have been employed to evaluate the antibacterial activity and in vitro cytotoxicity. The antibacterial effects of the gemini surfactants are performed on Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) with minimum inhibitory concentrations (MIC) ranging from 2.8 to 167.7 μM. Scanning electron microscopy (SEM) analysis results show that these surfactants interact with the bacterial cell membrane, disrupt the integrity of the membrane, and consequently kill the bacteria. The data recorded on C6 glioma and HEK293 human kidney cell lines using an MTT assay exhibit low half inhibitory concentrations (IC50). The influences of the gemini surfactants on the cell morphology, the cell migration ability, and the cell cycle are observed through hematoxylin-eosin (HE) staining, cell wound healing assay, and flow cytometric analyses, respectively. Both the values of MIC and IC50 decrease against the growth of the alkyl chain length of the gemini surfactants with the same spacer group. In the case of surfactants 12-s-12, the MICs and IC50s are found to decrease slightly with the spacer chain length changing from 2 to 8 and again to increase at higher spacer length (s = 10-12). All of the gemini surfactants show great antibacterial activity and cytotoxicity, and they might exhibit potential applications in medical fields.

  7. Structure-property relationship of quinuclidinium surfactants--Towards multifunctional biologically active molecules.

    Science.gov (United States)

    Skočibušić, Mirjana; Odžak, Renata; Štefanić, Zoran; Križić, Ivana; Krišto, Lucija; Jović, Ozren; Hrenar, Tomica; Primožič, Ines; Jurašin, Darija

    2016-04-01

    Motivated by diverse biological and pharmacological activity of quinuclidine and oxime compounds we have synthesized and characterized novel class of surfactants, 3-hydroxyimino quinuclidinium bromides with different alkyl chains lengths (CnQNOH; n=12, 14 and 16). The incorporation of non conventional hydroxyimino quinuclidinium headgroup and variation in alkyl chain length affects hydrophilic-hydrophobic balance of surfactant molecule and thereby physicochemical properties important for its application. Therefore, newly synthesized surfactants were characterized by the combination of different experimental techniques: X-ray analysis, potentiometry, electrical conductivity, surface tension and dynamic light scattering measurements, as well as antimicrobial susceptibility tests. Comprehensive investigation of CnQNOH surfactants enabled insight into structure-property relationship i.e., way in which the arrangement of surfactant molecules in the crystal phase correlates with their solution behavior and biologically activity. The synthesized CnQNOH surfactants exhibited high adsorption efficiency and relatively low critical micelle concentrations. In addition, all investigated compounds showed very potent and promising activity against Gram-positive and clinically relevant Gram-negative bacterial strains compared to conventional antimicrobial agents: tetracycline and gentamicin. The overall results indicate that bicyclic headgroup with oxime moiety, which affects both hydrophilicity and hydrophobicity of CnQNOH molecule in addition to enabling hydrogen bonding, has dominant effect on crystal packing and physicochemical properties. The unique structural features of cationic surfactants with hydroxyimino quinuclidine headgroup along with diverse biological activity have made them promising structures in novel drug discovery. Obtained fundamental understanding how combination of different functionalities in a single surfactant molecule affects its physicochemical

  8. Hot foam for weed control-Do alkyl polyglucoside surfactants used as foaming agents affect the mobility of organic contaminants in soil?

    Science.gov (United States)

    Cederlund, H; Börjesson, E

    2016-08-15

    Use of alkyl polyglucosides (APGs) as a foaming agent during hot water weed control may influence the environmental fate of organic contaminants in soil. We studied the effects of the APG-based foaming agent NCC Spuma (C8-C10) on leaching of diuron, glyphosate, and polycyclic aromatic hydrocarbons (PAHs) in sand columns. We also examined how APG concentration affected the apparent water solubility and adsorption of the herbicides and of the PAHs acenaphthene, acenaphthylene and fluorene. Application of APGs at the recommended concentration of 0.3% did not significantly affect leaching of any of the compounds studied. However, at a concentration of 1.5%, leaching of both diuron and glyphosate was significantly increased. The increased leaching corresponded to an increase in apparent water solubility of diuron and a decrease in glyphosate adsorption to the sand. However, APG addition did not significantly affect the mobility of PAHs even though their apparent water solubility was increased. These results suggest that application of APG-based foam during hot water weed control does not significantly affect the mobility of organic contaminants in soil if used according to recommendations. Moreover, they suggest that APGs could be useful for soil bioremediation purposes if higher concentrations are used.

  9. Alkyl Chain Length Dependent Structural and Orientational Transformations of Water at Alcohol-Water Interfaces and Its Relevance to Atmospheric Aerosols.

    Science.gov (United States)

    Mondal, Jahur A; Namboodiri, V; Mathi, P; Singh, Ajay K

    2017-04-06

    Although the hydrophobic size of an amphiphile plays a key role in various chemical, biological, and atmospheric processes, its effect at macroscopic aqueous interfaces (e.g., air-water, oil-water, cell membrane-water, etc.), which are ubiquitous in nature, is not well understood. Here we report the hydrophobic alkyl chain length dependent structural and orientational transformations of water at alcohol (CnH2n+1OH, n = 1-12)-water interfaces using interface-selective heterodyne-detected vibrational sum frequency generation (HD-VSFG) and Raman multivariate curve resolution (Raman-MCR) spectroscopic techniques. The HD-VSFG results reveal that short-chain alcohols (CnH2n+1OH, n alcohols (CnH2n+1OH, n > 4, i.e., beyond 1-butanol) make the interfacial water more strongly H-bonded and reversely orientated; the OH stretch band maximum appears at ∼3200 cm(-1), and the H atoms are pointed away from the bulk water, that is, "H-up" oriented. Interestingly, for the alcohol of intermediate chain length (CnH2n+1OH, n = 4, i.e, 1-butanol), the interface is quite unstable even after hours of its formation and the time-averaged result is qualitatively similar to that of the long-chain alcohols, indicating a structural/orientational crossover of interfacial water at the 1-butanol-water interface. pH-dependent HD-VSFG measurements (with H2O as well as isotopically diluted water, HOD) suggest that the structural/orientational transformation of water at the long-chain alcohol-water interface is associated with the adsorption of OH(-) anion at the interface. Vibrational mapping of the water structure in the hydration shell of OH(-) anion (obtained by Raman-MCR spectroscopy of NaOH in HOD) clearly shows that the water becomes strongly H-bonded (OH stretch max. ≈ 3200 cm(-1)) while hydrating the OH(-) anion. Altogether, it is conceivable that alcohols of different hydrophobic chain lengths that are present in the troposphere will differently affect the interfacial electrostatics and

  10. Effects of alkyl polyglycoside, a nonionic surfactant, and forage-to-concentrate ratio on rumen fermentation, amino acid composition of rumen content, bacteria and plasma in goats.

    Science.gov (United States)

    Zeng, Bo; Tan, Zhiliang; Tang, Shaoxun; Han, Xuefeng; Tan, Chuanyan; Zhong, Rongzhen; Hea, Zhixiong; Arigbede, Oluwasanmi Moses

    2011-06-01

    In the present study, the effects of different forage-to-concentrate ratios (F:C) and an alkyl polyglycoside (APG) supplementation on parameters of rumen and blood metabolism were investigated in goats. A 2 x 2 factorial experiment was arranged within a 4 x 4 Latin square design (four 22-day periods), using four wether goats equipped with permanent ruminal cannulas. The experimental diets included two F:C levels (40:60 vs. 60:40), and two APG supplementation levels (None or 13 ml APG daily per animal). Rumen contents and blood samples were collected at the end of each period. Dietary F:C alteration affected plasma urea and influenced the proportions of leucine, histidine, arginine, glycine, proline, alanine, valine, phenylalanine, cysteine and tyrosine in rumen content, and the proportions of methionine, threonine and proline in solid-associated bacteria (SAB) significantly. Dietary APG decreased the proportions of valine and phenylalanine in rumen content, and the histidine content of liquid-associated bacteria. The interaction between dietary F:C and APG was significant for the proportions of glycine and alanine in rumen content, and the proportions of lysine and threonine in SAB. The proportion of lysine was greater, but the proportion of threonine was less in SAB for goats fed high F:C diet without APG supplementation. The proportions of plasma free amino acids and glucose concentration were not affected by experimental treatments. These results indicated that dietary APG addition affected the amino acid composition of the rumen content and ruminal bacteria, but this depended on the dietary F:C ratio. It is necessary to validate the effectiveness of dietary APG supplementation in further studies with more animals.

  11. The physicochemistry and percolation behavior of microemulsions as a function of chain length of cosurfactant and surfactant

    National Research Council Canada - National Science Library

    Purva Thatai; Ashok K. Tiwary; Bharti Sapra

    2016-01-01

    ...) stabilized by mixtures containing polysorbates (C12-C18) as surfactants and n-alkanols (C2-C6) as cosurfactants. Distribution coefficients and Gibbs free energy were also determined for the systems containing polyoxyethylene sorbitan monolaurate...

  12. Biodegradability and aquatic toxicity of quaternary ammonium-based gemini surfactants: Effect of the spacer on their ecological properties.

    Science.gov (United States)

    Garcia, M Teresa; Kaczerewska, Olga; Ribosa, Isabel; Brycki, Bogumił; Materna, Paulina; Drgas, Małgorzata

    2016-07-01

    Aerobic biodegradability and aquatic toxicity of five types of quaternary ammonium-based gemini surfactants have been examined. The effect of the spacer structure and the head group polarity on the ecological properties of a series of dimeric dodecyl ammonium surfactants has been investigated. Standard tests for ready biodegradability assessment (OECD 310) were conducted for C12 alkyl chain gemini surfactants containing oxygen, nitrogen or a benzene ring in the spacer linkage and/or a hydroxyethyl group attached to the nitrogen atom of the head groups. According to the results obtained, the gemini surfactants examined cannot be considered as readily biodegradable compounds. The negligible biotransformation of the gemini surfactants under the standard biodegradation test conditions was found to be due to their toxic effects on the microbial population responsible for aerobic biodegradation. Aquatic toxicity of gemini surfactants was evaluated against Daphnia magna. The acute toxicity values to Daphnia magna, IC50 at 48 h exposure, ranged from 0.6 to 1 mg/L. On the basis of these values, the gemini surfactants tested should be classified as toxic or very toxic to the aquatic environment. However, the dimeric quaternary ammonium-based surfactants examined result to be less toxic than their corresponding monomeric analogs. Nevertheless the aquatic toxicity of these gemini surfactants can be reduced by increasing the molecule hydrophilicity by adding a heteroatom to the spacer or a hydroxyethyl group to the polar head groups.

  13. Phospholipid bilayer-perturbing properties underlying lysis induced by pH-sensitive cationic lysine-based surfactants in biomembranes.

    Science.gov (United States)

    Nogueira, Daniele Rubert; Mitjans, Montserrat; Busquets, M Antonia; Pérez, Lourdes; Vinardell, M Pilar

    2012-08-14

    Amino acid-based surfactants constitute an important class of natural surface-active biomolecules with an unpredictable number of industrial applications. To gain a better mechanistic understanding of surfactant-induced membrane destabilization, we assessed the phospholipid bilayer-perturbing properties of new cationic lysine-based surfactants. We used erythrocytes as biomembrane models to study the hemolytic activity of surfactants and their effects on cells' osmotic resistance and morphology, as well as on membrane fluidity and membrane protein profile with varying pH. The antihemolytic capacity of amphiphiles correlated negatively with the length of the alkyl chain. Anisotropy measurements showed that the pH-sensitive surfactants, with the positive charge on the α-amino group of lysine, significantly increased membrane fluidity at acidic conditions. SDS-PAGE analysis revealed that surfactants induced significant degradation of membrane proteins in hypo-osmotic medium and at pH 5.4. By scanning electron microscopy examinations, we corroborated the interaction of surfactants with lipid bilayer. We found that varying the surfactant chemical structure is a way to modulate the positioning of the molecule inside bilayer and, thus, the overall effect on the membrane. Our work showed that pH-sensitive lysine-based surfactants significantly disturb the lipid bilayer of biomembranes especially at acidic conditions, which suggests that these compounds are promising as a new class of multifunctional bioactive excipients for active intracellular drug delivery.

  14. Quantum state-resolved molecular scattering of NO (2Π1 /2) at the gas-[Cnmim][Tf2N] room temperature ionic liquid interface: Dependence on alkyl chain length, collision energy, and temperature

    Science.gov (United States)

    Zutz, Amelia; Nesbitt, David J.

    2016-10-01

    Room temperature ionic liquids (RTILs) represent a promising class of chemically tunable, low vapor pressure solvents with myriad kinetic applications that depend sensitively on the nature of gas-molecule interactions at the liquid surface. This paper reports on rovibronically inelastic dynamics at the gas-RTIL interface, colliding supersonically cooled hyperthermal molecular beams of NO (1/2 2Π, N = 0) from 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (or [Cnmim][Tf2N]) and probing the scattered NO molecules via laser induced fluorescence (LIF) from the A(2Σ ) state. Specifically, inelastic energy transfer into NO rovibrational and electronic degrees of freedom is explored as a function of RTIL alkyl chain length (n), incident collision energy (Einc) and surface temperature (Ts). At low collision energies (Einc = 2.7(9) kcal/mol), the scattered NO molecules exhibit a rotational temperature (Trot) systematically colder than Ts for all chain lengths, which signals the presence of non-equilibrium dynamics in the desorption channel. At high collision energies (Einc = 20(2) kcal/mol), microscopic branching into trapping/desorption (TD) and impulsive scattering (IS) pathways is clearly evident, with the TD fraction (α ) exhibiting a step-like increase between short (n = 2, 4) and long (n = 8, 12, 16) alkyl chains consistent with theoretical predictions. For all hydrocarbon chain lengths and RTIL temperature conditions, NO rotational excitation in the IS channel yields hyperthermal albeit Boltzmann-like distributions well described by a "temperature" (TIS = 900 -1200 K) that decreases systematically with increasing n. Non-adiabatic, collision induced hopping between ground and excited spin-orbit states is found to be independent of RTIL alkyl chain length and yet increase with collision energy. The scattering data confirm previous experimental reports of an enhanced presence of the alkyl tail at the gas-RTIL interface with increasing n, as well as

  15. Quantum state-resolved molecular scattering of NO (2Π1/2 at the gas-[Cnmim][Tf2N] room temperature ionic liquid interface: Dependence on alkyl chain length, collision energy, and temperature

    Directory of Open Access Journals (Sweden)

    Amelia Zutz

    2016-10-01

    Full Text Available Room temperature ionic liquids (RTILs represent a promising class of chemically tunable, low vapor pressure solvents with myriad kinetic applications that depend sensitively on the nature of gas-molecule interactions at the liquid surface. This paper reports on rovibronically inelastic dynamics at the gas-RTIL interface, colliding supersonically cooled hyperthermal molecular beams of NO (Π1/22, N = 0 from 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonylimide (or [Cnmim][Tf2N] and probing the scattered NO molecules via laser induced fluorescence (LIF from the A(2Σ state. Specifically, inelastic energy transfer into NO rovibrational and electronic degrees of freedom is explored as a function of RTIL alkyl chain length (n, incident collision energy (Einc and surface temperature (Ts. At low collision energies (Einc = 2.7(9 kcal/mol, the scattered NO molecules exhibit a rotational temperature (Trot systematically colder than Ts for all chain lengths, which signals the presence of non-equilibrium dynamics in the desorption channel. At high collision energies (Einc = 20(2 kcal/mol, microscopic branching into trapping/desorption (TD and impulsive scattering (IS pathways is clearly evident, with the TD fraction (α exhibiting a step-like increase between short (n = 2, 4 and long (n = 8, 12, 16 alkyl chains consistent with theoretical predictions. For all hydrocarbon chain lengths and RTIL temperature conditions, NO rotational excitation in the IS channel yields hyperthermal albeit Boltzmann-like distributions well described by a “temperature” (TIS = 900 -1200 K that decreases systematically with increasing n. Non-adiabatic, collision induced hopping between ground and excited spin-orbit states is found to be independent of RTIL alkyl chain length and yet increase with collision energy. The scattering data confirm previous experimental reports of an enhanced presence of the alkyl tail at the gas-RTIL interface with increasing n, as well as

  16. I. Enabling Single-Chain Surfactants to Form Vesicles by Nonamphiphilic Liquid Crystals in Water II. Controlling Attachment and Ligand-Mediated Adherence of Candida albicans on Monolayers

    Science.gov (United States)

    Varghese, Nisha

    This dissertation describes a fundamental study of weak noncovalent interactions and surface forces that exist at the interfaces of various interacting moieties (small molecules or microbes), and its relevance to colloidal and material chemistry. Chapter 1 presents an emulsion system that enables single-chain anionic or nonionic surfactants to sequester and encapsulate certain water-soluble organic salts, leading to the formation of vesicles in water. The water-soluble organic salt in the system comprises of disodium cromoglycate crystals that are emulsified by surfactants in water to form stable liquid crystal droplets. The work provides an exception to the rule of geometric packing factor that dictates formation of micelles by the surfactants in water. Chapter 2 shows that the odd or even number of carbon atoms present in the aliphatic chain of surfactants affect the ability of surfactants to emulsify aqueous-based liquid crystals of disodium cromoglycate. Such an odd-even effect is frequently observed for solid state properties like melting point, heat of fusion and refractive index but is rarely observed for molecules present in solution. When mixed in water, anionic single-chain surfactants with odd number of carbon atoms emulsifies disodium cromoglycate to form liquid crystal droplets, while surfactants with even number of carbon atoms fail to emulsify disodium cromoglycate. Chapter 3 Bolaamphiphiles usually form vesicles only in extreme conditions or in the presence of surfactants. Here, we explore the co-assembly system of synthesized bolaamphiphiles and disodium cromoglycate in water. The combination of the self-assembly forces of the bolaamphiphile and self-associating property of disodium cromoglycate liquid crystals act together at the interface form a unique microemulsion of liquid crystal droplets of disodium cromoglycate embedded in liquid crystal phase. Chapter 4 describes a key event (adhesion) that precedes infections caused by Candida albicans

  17. Dendronized Polyimides Bearing Long-Chain Alkyl Groups and Their Application for Vertically Aligned Nematic Liquid Crystal Displays

    Directory of Open Access Journals (Sweden)

    Yusuke Tsuda

    2009-11-01

    Full Text Available Polyimides having dendritic side chains were investigated. The terphenylene diamine monomer having a first-generation monodendron, 3,4,5-tris(n-dodecyloxy-benzoate and the monomer having a second-generation monodendron, 3,4,5-tris[-3’,4’,5’-tri(n-dodecyloxybenzyloxy]benzoate were successfully synthesized and the corresponding soluble dendritic polyimides were obtained by polycondensation with conventional tetracarboxylic dianhydride monomers such as benzophenone tertracarboxylic dianhydride (BTDA. The two-step polymerizations in NMP that is a general method for the synthesis of soluble polyimides is difficult; however, the expected dendritic polyimides can be obtained in aromatic polar solvents such as m-cresol and pyridine. The solubility of these dendoronized polyimides is characteristic; soluble in common organic solvents such as dichloromethane, chloroform, toluene and THF. These dendronized polyimides exhibited high glass transition temperatures and good thermal stability in both air and under nitrogen. Their application as alignment layers for LCDs was investigated, and it was found that these polyimides having dendritic side chains were applicable for the vertically aligned nematic liquid crystal displays (VAN-LCDs.

  18. Evaluation and comparison of n-alkyl chain and polar ligand bonded stationary phases for protein separation in reversed-phase liquid chromatography.

    Science.gov (United States)

    Ding, Ling; Guo, Zhimou; Xiao, Yuansheng; Xue, Xingya; Zhang, Xiuli; Liang, Xinmiao

    2014-09-01

    Protein retention is very sensitive to the change of solvent composition in reversed-phase liquid chromatography for so called "on-off" mechanism, leading to difficulty in mobile phase optimization. In this study, a novel 3-chloropropyl trichlorosilane ligand bonded column was prepared for protein separation. The differences in retention characteristics between the 3-chloropropyl trichlorosilane ligand bonded column and n-alkyl chain modified (C2, C4, C8) stationary phases were elucidated by the retention equation l nk=a+cC(B). Retention parameters (a and c) of nine standard proteins with different molecular weights were calculated by using homemade software. Results showed that retention times of nine proteins were similar on four columns, but the 3-chloropropyl trichlorosilane ligand bonded column obtained the lowest retention parameter values of larger proteins. It meant that their retention behavior affected by acetonitrile concentration would be different due to lower |c| values. More specifically, protein elution windows were broader, and retentions were less sensitive to the change of acetonitrile concentration on the 3-chloropropyl trichlorosilane ligand bonded column than that on other columns. Meanwhile, the 3-chloropropyl trichlorosilane ligand bonded column displayed distinctive selectivity for some proteins. Our results indicated that stationary phase with polar ligand provided potential solutions to the "on-off" problem and optimization in protein separation.

  19. α-Gel formation by amino acid-based gemini surfactants.

    Science.gov (United States)

    Sakai, Kenichi; Ohno, Kiyomi; Nomura, Kazuyuki; Endo, Takeshi; Sakamoto, Kazutami; Sakai, Hideki; Abe, Masahiko

    2014-07-08

    Ternary mixtures being composed of surfactant, long-chain alcohol, and water sometimes form a highly viscous lamellar gel with a hexagonal packing arrangement of their crystalline hydrocarbon chains. This molecular assembly is called "α-crystalline phase" or "α-gel". In this study, we have characterized α-gels formed by the ternary mixtures of amino acid-based gemini surfactants, 1-hexadecanol (C16OH), and water. The surfactants used in this study were synthesized by reacting dodecanoylglutamic acid anhydride with alkyl diamines and abbreviated as 12-GsG-12 (s: the spacer chain length of 2, 5, and 8 methylene units). An amino acid-based monomeric surfactant, dodecanoylglutamic acid (12-Glu), was also used for comparison. At a fixed water concentration the melting point of the α-gel increased with increasing C16OH concentration, and then attained a saturation level at the critical mole ratio of 12-GsG-12/C16OH = 1/2 under the normalization by the number of hydrocarbon chains of the surfactants. This indicates that, to obtain the saturated α-gel, a lesser amount of C16OH is required for the gemini surfactants than for the monomeric one (the critical mole ratio of 12-Glu/C16OH = 1/3). Small- and wide-angle X-ray scattering measurements demonstrated an increase in the long-range d-spacing of the saturated α-gels in the order 12-Glu gels at a given water concentration. This is caused by the decreased amount of excess water being present outside the α-gel structure (or the increased amount of water incorporated between the surfactant-alcohol bilayers). To the best of our knowledge, this is the first report focusing on the formation of α-gel in gemini surfactant systems.

  20. Synthesis and fungicidal activity of some alkyl – 2,4 ...

    African Journals Online (AJOL)

    In vitro fungicidal assay of these alkyl sulfenate esters against Aspergillus flavus, Rhizopus stolonifer ... Increase in chain length of the alkyl substituents was found to reduce the fungicidal activity of the alkyl sulfenate esters. ... Article Metrics.

  1. Amphiphilic biopolymers (amphibiopols) as new surfactants for membrane protein solubilization

    Science.gov (United States)

    Duval-Terrié, Caroline; Cosette, Pascal; Molle, Gérard; Muller, Guy; Dé, Emmanuelle

    2003-01-01

    The aim of this study was to develop new surfactants for membrane protein solubilization, from a natural, biodegradable polymer: the polysaccharide pullulan. A set of amphiphilic pullulans (HMCMPs), differing in hydrophobic modification ratio, charge ratio, and the nature of the hydrophobic chains introduced, were synthesized and tested in solubilization experiments with outer membranes of Pseudomonas fluorescens. The membrane proteins were precipitated, and then resolubilized with various HMCMPs. The decyl alkyl chain (C10) was the hydrophobic graft that gave the highest level of solubilization. Decyl alkyl chain-bearing HMCMPs were also able to extract integral membrane proteins from their lipid environment. The best results were obtained with an amphiphilic pullulan bearing 18% decyl groups (18C10). Circular dichroism spectroscopy and membrane reconstitution experiments were used to test the structural and functional integrity of 18C10-solubilized proteins (OmpF from Escherichia coli and bacteriorhodopsin from Halobacterium halobium). Whatever their structure type (α or β), 18C10 did not alter either the structure or the function of the proteins analyzed. Thus, HMCMPs appear to constitute a promising new class of polymeric surfactants for membrane protein studies. PMID:12649425

  2. Spontaneous surface self-assembly in protein-surfactant mixtures: interactions between hydrophobin and ethoxylated polysorbate surfactants.

    Science.gov (United States)

    Tucker, Ian M; Petkov, Jordan T; Penfold, Jeffrey; Thomas, Robert K; Li, Peixun; Cox, Andrew R; Hedges, Nick; Webster, John R P

    2014-05-01

    The synergistic interactions between certain ethoxylated polysorbate nonionic surfactants and the protein hydrophobin result in spontaneous self-assembly at the air-water interface to form layered surface structures. The surface structures are characterized using neutron reflectivity. The formation of the layered surface structures is promoted by the hydrophobic interaction between the polysorbate alkyl chain and the hydrophobic patch on the surface of the globular hydrophobin and the interaction between the ethoxylated sorbitan headgroup and hydrophilic regions of the protein. The range of the ethoxylated polysorbate concentrations over which the surface ordering occurs is a maximum for the more hydrophobic surfactant polyoxyethylene(8) sorbitan monostearate. The structures at the air-water interface are accompanied by a profound change in the wetting properties of the solution on hydrophobic substrates. In the absence of the polysorbate surfactant, hydrophobin wets a hydrophobic surface, whereas the hydrophobin/ethoxylated polysorbate mixtures where multilayer formation occurs result in a significant dewetting of hydrophobic surfaces. The spontaneous surface self-assembly for hydrophobin/ethoxylated polysorbate surfactant mixtures and the changes in surface wetting properties provide a different insight into protein-surfactant interactions and potential for manipulating surface and interfacial properties and protein surface behavior.

  3. Influence of Alkyl Chain Length and Structure on the Extraction of Copper(II) from Aqueous Acid by 5-Alkyl-2-hydroxybenzaldoximes in Hydrocarbon Solvents: Diffusion Coefficients of Extractants and Their Complexes.

    Science.gov (United States)

    Ainscow; Aldalur; Beezer; Connor; Garbett; Mitchell; Page; Tindale; Turner; Willson

    1999-05-01

    Measurement of the kinetics of extraction of copper(II) by 19 different 5-alkyl-2-hydroxybenzaldoximes (alkyl is C7H15 and C9H19) from acidic (hydrogen sulfate buffer) aqueous solution in the range pH 3.4-2.0, into 20% v/v toluene in n-hexane is reported. The lowering of the interfacial tension has been measured in some cases. The solubility of the extractants in water has been measured spectrophotometrically. A modified Taylor-Aris dispersion technique has been used to measure the diffusion coefficients in n-hexane and Orfom SX7 of some of the extractants and of the copper(II) complexes which they form. At low initial bulk concentrations (<10 mol m-3) of the extractants, the rate of extraction is controlled by the rate of diffusion of the extractant from the bulk to the organic-aqueous interface. The diffusion coefficient is related to the steric bulk of the alkyl substituent. At higher initial bulk concentrations (200 mol m-3) of the extractants, when the interface is saturated, the rate of extraction is inversely related to the apparent steric bulk of the alkyl substituent. Copyright 1999 Academic Press.

  4. Influence of alkyl chain length and structure on the extraction of copper(II) from aqueous acid by 5-alkyl-2-hydroxybenzaldoximes in hydrocarbon solvents: Diffusion coefficients of extractants and their complexes

    Energy Technology Data Exchange (ETDEWEB)

    Ainscow, T.A.; Aldalur, I.; Beezer, A.E. [Univ. of Kent, Canterbury (United Kingdom). School of Physical Sciences] [and others

    1999-05-01

    Measurement of the kinetics of extraction of copper(II) by 19 different 5-alkyl-2-hydroxybenzaldoximes (alkyl is C{sub 7}H{sub 15} and C{sub 9}H{sub 19}) from acidic (hydrogen sulfate buffer) aqueous solution in the range pH 3.4--2.0, into 20% v/v toluene in n-hexane is reported. The lowering of the interfacial tension has been measured in some cases. The solubility of the extractants in water has been measured spectrophotometrically. A modified Taylor-Aris dispersion technique has been used to measure the diffusion coefficients in n-hexane and Orfom SX7 of some of the extractants and of the copper(II) complexes which they form. At low initial bulk concentrations (<10 mol m{sup {minus}1}) of the extractants, the rate of extraction is controlled by the rate of diffusion of the extractant from the bulk to the organic-aqueous interface. The diffusion coefficient is related to the steric bulk of the alkyl substituent. At higher initial bulk concentrations (200 mol m{sup {minus}1}) of the extractants, when the interface is saturated, the rate of extraction is inversely related to the apparent steric bulk of the alkyl substituent.

  5. Surfactant-enhanced cellulose nanocrystal Pickering emulsions.

    Science.gov (United States)

    Hu, Zhen; Ballinger, Sarah; Pelton, Robert; Cranston, Emily D

    2015-02-01

    The effect of surfactants on the properties of Pickering emulsions stabilized by cellulose nanocrystals (CNCs) was investigated. Electrophoretic mobility, interfacial tension, confocal microscopy and three-phase contact angle measurements were used to elucidate the interactions between anionic CNCs and cationic alkyl ammonium surfactants didecyldimethylammonium bromide (DMAB) and cetyltrimethylammonium bromide (CTAB). Both surfactants were found to adsorb onto CNCs with concentration-dependent morphology. At low concentrations, individual surfactant molecules adsorbed with alkyl tails pointing outward leading to hydrophobic CNCs. At higher concentrations, above the surfactant's apparent critical micelle concentration, surfactant aggregate morphologies on CNCs were inferred and the hydrophobicity of CNCs decreased. DMAB, which has two alkyl tails, rendered the CNCs more hydrophobic than CTAB which has only a single alkyl tail, at all surfactant concentrations. The change in CNC wettability from surfactant adsorption was directly linked to emulsion properties; adding surfactant increased the emulsion stability, decreased the droplet size, and controlled the internal phase of CNC Pickering emulsions. More specifically, a double transitional phase inversion, from oil-in-water to water-in-oil and back to oil-in-water, was observed for emulsions with CNCs and increasing amounts of DMAB (the more hydrophobic surfactant). With CNCs and CTAB, no phase inversion was induced. This work represents the first report of CNC Pickering emulsions with surfactants as well as the first CNC Pickering emulsions that can be phase inverted. The ability to surface modify CNCs in situ and tailor emulsions by adding surfactants may extend the potential of CNCs to new liquid formulations and extruded/spray-dried materials.

  6. Interactions and hybrid complex formation of anionic algal polysaccharides with a cationic glycine betaine-derived surfactant.

    Science.gov (United States)

    Covis, Rudy; Vives, Thomas; Gaillard, Cédric; Benoit, Maud; Benvegnu, Thierry

    2015-05-01

    The interaction between anionic algal polysaccharides ((κ)-, (ι)-, (λ)-carrageenans, alginate and ulvan) and a cationic glycine betaine (GB) amide surfactant possessing a C18:1 alkyl chain has been studied using isothermal titration calorimetry (ITC), zeta-potential measurements, dynamic light scattering (DLS), transmission electron microscopy (TEM), atomic force microscopy (AFM), and surface tension measurements. It was observed that this cationic surfactant derived from renewable raw materials induced cooperative binding with the anionic polymers at critical aggregation concentration (CAC) and the CAC values are significantly lower than the corresponding critical micelle concentration (CMC) for the surfactant. The CMC of cationic GB surfactant was obtained at higher surfactant concentration in polysaccharide solution than in pure water. More interestingly, the presence of original polysaccharide/surfactant hybrid complexes formed above the CMC value was evidenced from (κ)-carrageenan by microscopy (TEM and AFM). Preliminary investigations of the structure of these complexes revealed the existence of surfactant nanoparticles surrounded with polysaccharide matrix, probably resulting from electrostatic attraction. In addition, ITC measurements clearly showed that the interactions of the κ-carrageenan was stronger than for other polysaccharides ((ι)-, (λ)-carrageenans, alginate and ulvan). These results may have important impact on the use of the GB amide surfactant in formulations based on algal polysaccharides for several applications such as in food, cosmetics, and detergency fields.

  7. Adsorption of the disinfectant benzalkonium chloride on montmorillonite. Synergistic effect in mixture of molecules with different chain lengths.

    Science.gov (United States)

    Zanini, Graciela P; Ovesen, Rikke Gleerup; Hansen, H C B; Strobel, Bjarne W

    2013-10-15

    The biocide benzalkonium chloride (BAC) is a mix of cationic alkylbenzyldimethylammonium surfactants having different alkyl chain lengths. A comparative study of adsorption on the phyllosilicate clay montmorillonite of two of these surfactants, with alkyl chains having respectively 12 C atoms (BAC-12) and 14 C atoms (BAC-14), and a mixture of both surfactants is presented in this work. Adsorption isotherms were performed for individual surfactants and for a 1:1 mixture BAC-12+BAC-14. The adsorption was investigated in an ample concentration range that covers almost seven orders of magnitude in concentrations (from 1 nM to 10 mM), range that includes environmentally relevant concentrations. Quantification of BAC was performed by HPLC-UV and LC-MS and the results were completed with powder X-Ray diffraction. The adsorption of both surfactants leads to adsorption isotherms with two well differentiated steps. The first step corresponds almost exclusively to a cation exchange process, and the binding constant is very similar for both surfactants. The second step of the isotherms is observed at higher concentrations and adsorption is mainly driven by lateral interactions between surfactant molecules. The binding constant of this step is larger for BAC-14 than for BAC-12. Adsorption from a BAC-12+BAC-14 mixture shows a synergistic behaviour, possibly due to a better packing arrangement in the interlayer. Calculations show that in natural systems silicate clays are major sorbents of BAC at low concentrations whereas binding to humic acid is predominant at high concentrations.

  8. Effect of surfactants on the properties of hydrotalcites prepared by the reverse micelle method

    Energy Technology Data Exchange (ETDEWEB)

    Holgado, Patricia H., E-mail: h.holgado@usal.es; Holgado, María J., E-mail: holgado@usal.es; San Román, María S., E-mail: sanroman@usal.es; Rives, Vicente, E-mail: vrives@usal.es

    2015-02-01

    Layered double hydroxides with the hydrotalcite-type structure have been prepared by the reverse micelles method. The layer cations were Ni{sup 2+} and Fe{sup 3+} in all cases and the interlayer anion was carbonate. We have studied the effect of the surfactant used (with linear chains of different lengths, or cyclic) and the effect of the pH on the properties of the solids formed. These have been characterized by element chemical analysis, powder X-ray diffraction, thermogravimetric analysis, temperature-programmed reduction, FT-IR and Vis–UV spectroscopies and scanning electron microscopy. It has been found that the samples prepared at pH 9 are more crystalline than those prepared at pH 11 and their crystallite sizes are always larger than for samples prepared by the conventional precipitation method. Surfactants with cyclic organic chains lead to a larger crystallite size, probably because the water pool vesicle where the crystallite grows is larger due to sterical hindrance of the organic chains. - Graphical abstract: Layered double hydroxides with the hydrotalcite-type structure with Ni{sup 2+} and Fe{sup 3+} cations in the layers have been prepared by the reverse micelles method. Different surfactants were used at different pH synthesis. Samples prepared at pH 9 are higher crystalline than those prepared at pH 11. Surfactants with cyclic organic chains lead to a larger crystallite size. - Highlights: • Hydrotalcites were prepared by the micelles reverse method. • Straight alkyl or cyclic chain surfactants were used. • All hydrotalcites are well crystallized at pH = 9 and 11. • The crystallite size depends on the linear/cyclic nature of the surfactant chain.

  9. Impact of the degree of ethoxylation of the ethoxylated polysorbate nonionic surfactant on the surface self-assembly of hydrophobin-ethoxylated polysorbate surfactant mixtures.

    Science.gov (United States)

    Penfold, Jeffrey; Thomas, Robert K; Li, Peixun; Petkov, Jordan T; Tucker, Ian; Cox, Andrew R; Hedges, Nick; Webster, John R P; Skoda, Maximilian W A

    2014-08-19

    Neutron reflectivity measurements have been used to study the surface adsorption of the polyethylene sorbitan monostearate surfactant, with degrees of ethoxylation varying from 3 to 20 ethylene oxide groups, with the globular protein hydrophobin. The surface interaction between the ethoxylated polysorbate nonionic surfactants and the hydrophobin results in self-assembly at the air-solution interface in the form of a well-defined layered surface structure. The surface interaction arises from a combination of the hydrophobic interaction between the surfactant alkyl chain and the hydrophobic patch on the surface of the hydrophobin, and the hydrophilic interaction between the ethoxylated sorbitan headgroup and the hydrophilic regions on the surface of the hydrophobin. The results presented show that varying the degree of ethoxylation of the polysorbate surfactant changes the interaction between the surfactant and the hydrophobin and the packing, and hence the evolution in the resulting surface structure. The optimal degree of ethoxylation for multilayer formation is over a broad range, from of order 6 to 17 ethylene oxide groups, and for degrees of ethoxylation of 3 and 20 only monolayer adsorption of either the surfactant or the hydrophobin is observed.

  10. Solid-state phosphorescence of trans-bis(salicylaldiminato)platinum(II) complexes bearing long alkyl chains: morphology control towards intense emission.

    Science.gov (United States)

    Komiya, Naruyoshi; Itami, Nao; Naota, Takeshi

    2013-07-15

    Morphology control for intense solid-state phosphorescence of non-emissive, but potentially emissive crystals of platinum complexes and the mechanistic rationale are described. A series of trans-bis(salicylaldiminato)platinum(II) complexes bearing linear alkyl chains (1a: n=5; 1b: n=8; 1c: n=12; 1d: n=14; 1e: n=16; 1f: n=18) was synthesized and the solid-state emission properties were examined by using crystals/aggregates prepared under various precipitation conditions. Crystals of 1e, prepared using "kinetic" conditions including rapid cooling, high concentrations, and poor solvents, emit intensive yellow phosphorescence (λ(max)=545 nm) under UV irradiation at 298 K with an absolute quantum efficiency of 0.36, whereas all the crystals of 1a-1f prepared using "thermodynamic" conditions including slow cooling, low concentrations, and good solvents were either non- or less emissive with Φ(298K) values of 0.12 (1a), 0.11 (1b), 0.10 (1c), 0.07 (1d), 0.02 (1e), and 0.02 (1f) under the same measurement conditions. The amorphous solid 1e, prepared by rapid cooling and freeze-drying, was also non-emissive (Φ(298K)=0.02, 0.02). Temperature-dependent emission spectra showed that the kinetic crystals of 1e exhibit high heat-resistance towards emission decay with increasing temperature, whereas the amorphous solid 1e is entirely heat-quenchable. This is a rare example of the change from a non-emissive crystal into a highly emissive crystal by morphology control through crystal engineering. Emission spectra and powder X-ray diffraction (XRD) patterns of the emissive, kinetic crystals of 1e are clearly distinct from those of the less emissive, thermodynamic crystals of 1a-1f. Single-crystal XRD unequivocally establishes that the thermodynamic crystals of 1d have a multilayered lamellar structure supported by highly regulated, consecutive π-stacking interactions between imine moieties, whereas the kinetic crystals of 1e have a face-to-edge lamellar structure with less

  11. The effects of surfactants on penetration across the skin*.

    Science.gov (United States)

    Walters, K A; Bialik, W; Brain, K R

    1993-12-01

    Synopsis Many of the properties of surfactants can be related to their ability to concentrate at phase interfaces, leading to a reduction in interracial tension. In biological systems the effects of surfactants are complex, particularly their effect on cell and other membranes, and this can lead to alterations in permeability characteristics. This is of particular relevance when considering the stratum corneum which has long been recognized as the major barrier to skin permeation. The magnitude of skin barrier function alteration is dependent on surfactant structure, both the hydrophobic alkyl chain and the hydropnilic ethylene oxide chain demonstrating some structure-activity behaviour. In many biological systems, including skin, surfactants with a similar hydrophilic group will show maximum membrane activity if they possess a decyl or dodecyl alkyl chain. It is difficult to rationalise this phenomenon, given that such solution properties as partition coefficients and CMCs do not show maxima or minima at these chain lengths. It may be that the physical parameters and molecular dimensions of the decyl/dodecyl chain provide the optimal ability to intercalate with the lipid bilayer structure. There is little doubt that once the surfactant has intercalated with the lipid bilayers in the lamellar liquid crystals of the stratum corneum, fluidity in the hydrophobic regions is increased. Effectively, this leads to a looser, more permeable structure. The significance of data obtained using commercially available surfactants, however, can be questioned on the grounds of purity. The purpose of this review is to describe some of the methods used to evaluate the effects of surfactants on the skin barrier and to discuss recent attempts to predict surfactant action on the skin using various biological and physical techniques. Résumé La plupart des propriétés des surfactants dépend de leur facilitéà se concentrer aux interfaces, menant ainsi à la réduction de la tension

  12. Stabilization of emulsions using polymeric surfactants based on inulin.

    Science.gov (United States)

    Tadros, Th F; Vandamme, A; Levecke, B; Booten, K; Stevens, C V

    2004-05-20

    The use of polymeric surfactants for stabilization of emulsions is described. A brief account of general classification and description of polymeric surfactants is given. This is followed by a description of the adsorption and conformation of polymeric surfactants at interfaces. The theoretical approaches for studying polymer adsorption are briefly described. This is followed by a section on the experimental techniques that can be applied to study adsorption and conformation of polymers at the interface. Examples are given to illustrate the experimental techniques. A section is devoted to the interaction between droplets containing adsorbed polymer layers (steric stabilization). The last section gives results on oil-in-water (O/W) emulsions stabilised with a novel graft copolymeric surfactant based on inulin that has been modified by introducing alkyl groups. Two oils were used, namely Isopar M (isoparaffinic oil) and cyclomethicone. Emulsions prepared using the inulin-based surfactant have large droplets, but this could be significantly reduced by addition of a cosurfactant in the oil phase, namely Span 20. The stability of the emulsions was investigated in water, in 0.5, 1.0, 1.5 and 2 mol dm(-3) NaCl and in 0.5, 1.0, 1.5 and 2 mol dm(-3) MgSO(4). These emulsions were stable for more than 1 year up to 50 degrees C in NaCl concentrations up to 2 mol dm(-3) and 1 mol dm(-3) MgSO(4). This high stability in high electrolyte concentrations could be attributed to the nature of the hydrophilic (stabilizing) polyfructose chain. This was confirmed using cloud point measurements, which showed high hydration of the polyfructose chain in such high electrolyte concentrations. This ensured the long-term physical stability resulting from the strong steric repulsion between the polyfructose chains.

  13. Surfactants as microbicides and contraceptive agents: a systematic in vitro study.

    Directory of Open Access Journals (Sweden)

    Otilia V Vieira

    Full Text Available BACKGROUND: The urgent need for cheap and easy-to-use protection against both unwanted pregnancies and sexually transmitted diseases has stimulated considerable interest in the use of surfactants as microbicides, anti-viral, and contraceptive agents in recent years. In the present study we report a systematic in vitro evaluation of the microbicidal, anti-viral and contraceptive potential of cationic, anionic, zwitterionic, and non-ionic surfactants. METHODOLOGY/PRINCIPAL FINDINGS: Toxicity was evaluated in mammalian columnar epithelial (MDCK cells, human sperm cells, Candida albicans, Escherichia coli, Pseudomonas aeruginosa, Neisseria gonorrhoeae, Streptococcus agalactiae and Enterococcus faecalis. The inhibition of adenovirus and lentivirus infection of MDCK cells was also tested. A homologous series of cationic surfactants, alkyl-N,N,N-trimethylammonium bromides (C(nTAB, with varying alkyl chains were shown to be bactericidal and fungicidal at doses that were related to the surfactant critical micelle concentrations (CMC, all of them at concentrations significantly below the CMC. In general, bacteria were more susceptible to this surfactant group than C. albicans and this organism, in turn, was more susceptible than MDCK cells. This suggests that the C(nTAB may be useful as vaginal disinfectants only in so far as bacterial and fungal infections are concerned. None of the surfactants examined, including those that have been used in pre-clinical studies, showed inhibition of adenovirus or lentivirus infection of MDCK cells or spermicidal activity at doses that were sub-toxic to MDCK cells. CONCLUSIONS/SIGNIFICANCE: The results of this study lead us to propose that systematic analysis of surfactant toxicity, such as we report in the present work, be made a mandatory pre-condition for the use of these substances in pre-clinical animal and/or human studies.

  14. Perfluoroalkyl sulfonates cause alkyl chain length-dependent hepatic steatosis and hypolipidemia mainly by impairing lipoprotein production in APOE*3-leiden CETP mice

    NARCIS (Netherlands)

    Bijland, S.; Rensen, P.C.N.; Pieterman, E.J.; Maas, A.C.E.; Hoorn, J.W. van der; Erk, M.J. van; Havekes, L.M.; Dijk, K.W. van; Chang, S.C.; Ehresman, D.J.; Butenhoff, J.L.; Princen, H.M.G.

    2011-01-01

    Perfluorobutane sulfonate (PFBS), perfluorohexane sulfonate (PFHxS), and perfluorooctane sulfonate (PFOS) are stable perfluoroalkyl sulfonate (PFAS) surfactants, and PFHxS and PFOS are frequently detected in human biomonitoring studies. Some epidemiological studies have shown modest positive correla

  15. Self-Aggregation of Amphiphilic Dendrimer in Aqueous Solution: The Effect of Headgroup and Hydrocarbon Chain Length.

    Science.gov (United States)

    Zhang, Pei; Xu, Xiaohui; Zhang, Minghui; Wang, Jinben; Bai, Guangyue; Yan, Haike

    2015-07-28

    The self-aggregation of amphiphilic dendrimers G1QPAMCm based on poly(amidoamine) PAMAM possessing the same hydrophilic group but differing in alkyl chain length in aqueous solution was investigated. Differences in the chemical structures lead to significant specificities in the aggregate building process. A variety of physicochemical parameters presented monotonous regularity with the increase in alkyl chain length in multibranched structure, as traditional amphiphilic molecules. A significant difference, however, existed in the morphology and the microenvironment of the microdomain of the aggregates, with G1QPAMCm with an alkyl chain length of 16 intending to form vesicles. To obtain supporting information about the aggregation mechanism, the thermodynamic parameters of micellization, the free Gibbs energy ΔGmic, and the entropy ΔSmic were derived subsequently, of which the relationship between the hydrophobic chain length and the thermodynamic properties indicated that the self-assembly process was jointly driven by enthalpy and entropy. Other than traditional surfactants, the contribution of enthalpy has not increased identically to the increase in hydrophobic interactions, which depends on the ratio of the alkyl chain length to the radius in the headgroup. Continuous increases in the hydrophobic chain length from 12 to 16 lead to the intracohesion of the alkyl chain involved in the process of self-assembly, weakening the hydrophobic interactions, and the increase in -ΔHmic, which offers an explanation of the formation of vesicular structures.

  16. Influence of anionic surfactants on the electric percolation of AOT/isooctane/water microemulsions.

    Science.gov (United States)

    García-Río, L; Mejuto, J C; Pérez-Lorenzo, M; Rodríguez-Alvarez, A; Rodríguez-Dafonte, P

    2005-07-05

    A study was carried out concerning the influence of sodium alkyl sulfonates on the electric percolation of AOT/isooctane/water microemulsions ([AOT] = 0.5 M and W = [H2O]/[AOT] = 22.2). An important effect was observed with regard to the percolation temperature caused by the addition of small quantities of alkyl sulfonates (rho = [alkyl sulfonate]/[AOT] = 0.01). The short chain alkyl sulfonates (C3-C5) cause an increase in the percolation temperature, which in turn is reduced as we increase the chain length of the additive until we obtain a percolation temperature which is lower than that which is observed in the absence of an additive (C6-C8). For hydrocarbon chains of a greater length we can observe a new increase in the percolation temperature (C10-C18). This behavior has been explained as a consequence of (i) the incorporation of the additives at the interphase of the microemulsion and (ii) the geometric parameters of the different surfactants added to the microemulsion.

  17. Characteristics of sugar surfactants in stabilizing proteins during freeze-thawing and freeze-drying.

    Science.gov (United States)

    Imamura, Koreyoshi; Murai, Katsuyuki; Korehisa, Tamayo; Shimizu, Noriyuki; Yamahira, Ryo; Matsuura, Tsutashi; Tada, Hiroko; Imanaka, Hiroyuki; Ishida, Naoyuki; Nakanishi, Kazuhiro

    2014-06-01

    Sugar surfactants with different alkyl chain lengths and sugar head groups were compared for their protein-stabilizing effect during freeze-thawing and freeze-drying. Six enzymes, different in terms of tolerance against inactivation because of freeze-thawing and freeze-drying, were used as model proteins. The enzyme activities that remained after freeze-thawing and freeze-drying in the presence of a sugar surfactant were measured for different types and concentrations of sugar surfactants. Sugar surfactants stabilized all of the tested enzymes both during freeze-thawing and freeze-drying, and a one or two order higher amount of added sugar surfactant was required for achieving protein stabilization during freeze-drying than for the cryoprotection. The comprehensive comparison showed that the C10-C12 esters of sucrose or trehalose were the most effective through the freeze-drying process: the remaining enzyme activities after freeze-thawing and freeze-drying increased at the sugar ester concentrations of 1-10 and 10-100 μM, respectively, and increased to a greater extent than for the other surfactants at higher concentrations. Results also indicate that, when a decent amount of sugar was also added, the protein-stabilizing effect of a small amount of sugar ester through the freeze-drying process could be enhanced. © 2014 Wiley Periodicals, Inc. and the American Pharmacists Association.

  18. Interfacial behavior of pure surfactants for enhanced oil recovery. Part 1. A study on the adsorption and distribution of cetylbenzene sulfonate

    Energy Technology Data Exchange (ETDEWEB)

    Weihong Qiao; Liangjun Dong; Zhongkui Zhao; Jie Yang; Huamin Li; Zongshi Li [Dalian Univ. of Technology (China)

    2003-04-01

    The contents of pure alkyl benzene sulfonate surfactants in both the aqueous and oil phases were determined. The diffusion, adsorption and distribution of the surfactants in the oil and aqueous phases were studied at dynamic equilibrium and the effects of different structures on diffusion were investigated. N-nonane was used as the oil phase. The results indicate that the contents of the surfactants on both sides of the interface tend to increase with increasing sodium hydroxide and sodium chloride concentrations. The corresponding interfacial tensions, however, decrease gradually, and the quantities adsorbed at the oil-water interface reach a maximum value. The content of surfactant at the interface tends to be higher when the benzene ring is located near the middle of the carbon chain, so resulting in ultralow interfacial tension. (orig.)

  19. Effect of surfactant alkyl chain length on the dispersion, and thermal and dynamic mechanical properties of LDPE/organo-LDH composites

    National Research Council Canada - National Science Library

    Muksing, N; Magaraphan, R; Coiai, S; Passaglia, E

    2011-01-01

    Low density polyethylene/layered double hydroxide (LDH) composites were prepared via melt compounding using different kinds of organo-LDHs and polyethylene-grafted maleic anhydride as the compatibilizer...

  20. Structure-Antibacterial Activity Relationships of Imidazolium-Type Ionic Liquid Monomers, Poly(ionic liquids) and Poly(ionic liquid) Membranes: Effect of Alkyl Chain Length and Cations.

    Science.gov (United States)

    Zheng, Zhiqiang; Xu, Qiming; Guo, Jiangna; Qin, Jing; Mao, Hailei; Wang, Bin; Yan, Feng

    2016-05-25

    The structure-antibacterial activity relationship between the small molecular compounds and polymers are still elusive. Here, imidazolium-type ionic liquid (IL) monomers and their corresponding poly(ionic liquids) (PILs) and poly(ionic liquid) membranes were synthesized. The effect of chemical structure, including carbon chain length of substitution at the N3 position and charge density of cations (mono- or bis-imidazolium) on the antimicrobial activities against both Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was investigated by determination of minimum inhibitory concentration (MIC). The antibacterial activities of both ILs and PILs were improved with the increase of the alkyl chain length and higher charge density (bis-cations) of imidazolium cations. Moreover, PILs exhibited lower MIC values relative to the IL monomers. However, the antibacterial activities of PIL membranes showed no correlation to those of their analogous small molecule IL monomers and PILs, which increased with the charge density (bis-cations) while decreasing with the increase of alkyl chain length. The results indicated that antibacterial property studies on small molecules and homopolymers may not provide a solid basis for evaluating that in corresponding polymer membranes.

  1. Thermodynamic Investigation on Micellization of Cationic Gemini Surfactants with Nitrophenoxy Groups in Hydrophobic Chains%尾链含对硝基苯醚基团的阳离子Gemini表面活性剂的胶束化热力学

    Institute of Scientific and Technical Information of China (English)

    黄旭; 韩玉淳; 王毅琳

    2013-01-01

    is akin to a separate phase-precipitation.Based on these two models,an ITC curve of observed enthalpy change versus surfactant concentration allows the determination of CMC and the enthalpy of micellization (△Hrmic)of a surfactant.Other thermodynamic parameters related to micellization,namely the free energy (△Gmic),the entropy (△Smic)and the heat capacity of micellization (△Cp.mic) can be calculated from the experimentally determined CMC and △Hmic.In this paper,ITC and electrical conductivity were employed to investigate the micellization process of cationic gemini surfactants,N,N,N',N'-tetramethyl-N,N'-bis[10-(4-nitrophenoxy)alkyl]-l,6-hexanediammonium dibromide (Nm-6-mN,with m=8,10 and 12,which are the numbers of carbon in the hydrocarbon chains),in aqueous solutions.Both phase separation model and mass action model were used to obtain a series of thermodynamic parameters.The results show that the obtained△Hmic values based on the two models are very close,however,the obtained △Gmic values based on the two models are not consistent.In addition,the △Cp,mic of the micellization process is mainly from the dehydration contribution of hydrophobic alkyl chains of the surfactants,which means the nitrophenoxy group located in the hydrophobic chain still contacts with water after the micellization.Furthermore,the micellar aggregation number n can be obtained by employing the mass action model.The micellar aggregation number n decreases with the increase of the hydrophobic chain length.The reason is that the surfactant with longer hydrophobic chains prefers to form premicelles,leading to the decrease of the average aggregation number.

  2. Adsorption of alkyltrimethylammonium bromides at water/alkane interfaces: competitive adsorption of alkanes and surfactants.

    Science.gov (United States)

    Fainerman, V B; Mucic, N; Pradines, V; Aksenenko, E V; Miller, R

    2013-11-12

    The adsorption of members of the homologous series of alkyl trimethylammonium bromides (C(n)TAB) is studied at water/alkane interfaces by drop profile analysis tensiometry. The results are discussed in terms of a competitive adsorption process of alkane and surfactant molecules. A thermodynamic model, derived originally for the adsorption of surfactant mixtures, is adapted such that it describes a competitive adsorption of the surfactant molecules from the aqueous phase and alkane molecules from the oil phase. This new model involves the interspecies attraction coefficient, which mutually increases the adsorption activities of the alkane and C(n)TAB. The effects of the alkyl chain length n of C(n)TABs and the influence of the number of C atoms in the alkane chain are discussed, and the physical quantities are compared to those determined at the aqueous solution/air interface. The new theoretical model for aqueous solution/oil interfaces is also compared to a theory that does not consider the adsorption of alkane. The proposed new model demonstrates good agreement with the experimental data.

  3. Acute toxicity and relationship between metabolites and ecotoxicity during the biodegradation process of non-ionic surfactants: fatty-alcohol ethoxylates, nonylphenol polyethoxylate and alkylpolyglucosides.

    Science.gov (United States)

    Jurado, E; Fernández-Serrano, M; Núñez-Olea, J; Luzón, G; Lechuga, M

    2009-01-01

    The toxicity values of fatty-alcohol ethoxylates, nonylphenol polyethoxylate, and alkylpolyglucosides have been determined by applying assays with luminescent bacteria. Also, the relation between metabolites and ecotoxicity during the biodegradation process has been determined. The biodegradation tests were carried out according to the OECD 301 E test for ready biodegradability. In these tests a solution of the surfactant, representing the sole carbon source for the microorganisms, was tested in a mineral medium, inoculated and incubated under aerobic conditions in the dark. The toxicity of surfactants is related to their molecular structure (Quantitative Structure Activity Relationships, QSAR). For the alkylpolyglucosides, toxicity expressed as EC(50) is related with the critical micelle concentration (CMC), the hydrophilic-lipophilic balance (HLB) of the surfactant, and the hydrophobic alkyl chain (R). The results indicate that toxicity increased as the CMC decreased and as the hydrophobicity increased and R rose. For fatty-alcohol ethoxylates, parameters characteristic studied have been HLB, number of units of ethylene oxide and the alkyl chain length. Relationships found are in agreement with the fact that increasing the alkyl chain length leads to a lower EC(50), whereas increasing ethoxylation leads to a lower toxicity. An analysis of the behaviour of the toxicity and HLB again indicates that the toxicity was greater for surfactants with a smaller HLB. The evolution of the toxicity was studied over the biodegradation process, expressed as a percentage of inhibition. For all the non-ionic surfactants assayed, except for the nonylphenol polyethoxylate, a major decline was found in toxicity during the first days of the biodegradation assay and at all the concentrations tested.

  4. Anaerobic digestion of linear alkyl benzene sulfonates: biodegradation kinetics and metabolite analysis.

    Science.gov (United States)

    García, M T; Campos, E; Ribosa, I; Latorre, A; Sánchez-Leal, J

    2005-09-01

    In the present work the effect of the alkyl chain length and the position of the sulfophenyl substituent of the linear alkylbenzene sulfonates (LAS) on their anaerobic biodegradability have been investigated. Degradation kinetics of the linear alkyl benzene sulfonates homologues, 2phiC10LAS, 2phiC12LAS and 2phiC14LAS, have been studied. It has been also investigated the effect of the isomer type on the degradation rate of the LAS molecule through the comparative study of the 2phiC10LAS and 5phiC10LAS isomers. Batch anaerobic biodegradation tests were performed using sludge from the anaerobic digester of a wastewater treatment plant as microorganisms source. Ultimate biodegradation was evaluated from the biogas production whereas primary biodegradation was determined by specific analysis of the surfactant. LAS homologues and isomers showed a negligible primary biodegradation under anaerobic conditions. Furthermore, analysis of sulfophenyl carboxilates (SPC) by LC-MS indicated a low and constant level of these LAS degradation metabolites over the test period. These data are consistent with a minimal transformation of the LAS parent molecule in the anaerobic digesters. On the other hand, the addition of the shortest alkyl chain length homologues, decyl and dodecylbenzene sulfonates, reduces the biogas production whereas the most hydrophobic homologue, the tetradecylbenzene sulfonate, enhances the biogas production. This LAS homologue seems to increase the availability of organic compounds sorbed on the anaerobic sludge promoting their biodegradation.

  5. Molecular Dynamics Simulation for the Effect of Chain Length of Spacer and Tail of Cationic Gemini Surfactant on the Complex with Anionic Polyelectrolyte%连接基团与尾链长度对阳离子Gemini表面活性剂与阴离子聚电解质复合物影响的分子动力学模拟

    Institute of Scientific and Technical Information of China (English)

    徐毅; 冯剑; 尚亚卓; 刘洪来

    2007-01-01

    Interaction of anionic polyelectrolyte with cationic gemini surfactant has been investigated by coarse-grained molecular dynamics simulation. Polyelectrolyte facilitates the oppositely charged ionic surfactants to aggregate by suppressing the electrostatic repulsion between ionic head groups leading to the formation of micellar complex. With addition of surfactant, the conformation of polyion chain changes from stretched to random coiled to spherical, and at the same time more free micelles are formed by surfactants in mixtures. Increasing the length of spacer or tail chain in gemini surfactant will weaken its interaction with polyelectrolyte and simultaneously strengthen its tendency to self-assemble. The simulation results are consistent with experimental observations and reveal that the electrostatic interaction plays an important role in the interaction of polyelectrolyte with gemini surfactant.

  6. Physico-chemical properties and cytotoxic effects of sugar-based surfactants: Impact of structural variations.

    Science.gov (United States)

    Lu, Biao; Vayssade, Muriel; Miao, Yong; Chagnault, Vincent; Grand, Eric; Wadouachi, Anne; Postel, Denis; Drelich, Audrey; Egles, Christophe; Pezron, Isabelle

    2016-09-01

    Surfactants derived from the biorefinery process can present interesting surface-active properties, low cytotoxicity, high biocompatibility and biodegradability. They are therefore considered as potential sustainable substitutes to currently used petroleum-based surfactants. To better understand and anticipate their performances, structure-property relationships need to be carefully investigated. For this reason, we applied a multidisciplinary approach to systematically explore the effect of subtle structural variations on both physico-chemical properties and biological effects. Four sugar-based surfactants, each with an eight carbon alkyl chain bound to a glucose or maltose head group by an amide linkage, were synthesized and evaluated together along with two commercially available standard surfactants. Physico-chemical properties including solubility, Krafft point, surface-tension lowering and critical micellar concentration (CMC) in water and biological medium were explored. Cytotoxicity evaluation by measuring proliferation index and metabolic activity against dermal fibroblasts showed that all surfactants studied may induce cell death at low concentrations (below their CMC). Results revealed significant differences in both physico-chemical properties and cytotoxic effects depending on molecule structural features, such as the position of the linkage on the sugar head-group, or the orientation of the amide linkage. Furthermore, the cytotoxic response increased with the reduction of surfactant CMC. This study underscores the relevance of a methodical and multidisciplinary approach that enables the consideration of surfactant solution properties when applied to biological materials. Overall, our results will contribute to a better understanding of the concomitant impact of surfactant structure at physico-chemical and biological levels.

  7. ESR Studies on the Micellization Behaviors of a Series of Novel Asymmetric Gemini Surfactants

    Institute of Scientific and Technical Information of China (English)

    WU,Yi-Tian(吴一天); WANG,Jin-Ben(王金本); LIU,Ming-Hua(刘鸣华); LIANG,Wen-Ping(梁文平)

    2002-01-01

    The synthesis of a new series of asymmetric cationic gemini surfactant and the investigation of their miccellization behaviors by electronic spin resonance (ESR) as well as the surface tension measurements were reported. 4-Oxo-2,2,6,6-tetramethylpiperidine-N-oxyl (4-oxo-TEMPO) is used as the spin probe. The surfactants studied have the general formula [CnH2n+1 N+(CH3)2C6H12N+(CH3)2Cm H2m,1]Br2- , referred to as dimeric n-6-m surfactants, in which n and m are the numbers of carbon atoms in the asymmetric side alkyl chains. From the experimental data, rotational correlation time τc, surface tension and critical micelle concentration (cac) ,values, the physical properties of these new surfactants have preliminarily been evaluated. It is shown that this new series of asymmetric gmini surfactants has interesting micellization behaviors, and they are very different in aggregating tendency from their asymmetric analogues.

  8. Synthesis and Monolayer Behaviors of Succinic Acid-Type Gemini Surfactants Containing Semifluoroalkyl Groups.

    Science.gov (United States)

    Kawase, Tokuzo; Nagase, Youhei; Oida, Tatsuo

    2016-01-01

    In this work, novel succinic acid-type gemini surfactants containing semifluoroalkyl groups, dl- and meso-2,3-bis[Rf-(CH2)n]-succinic acids (Rf = C4F9, C6F13, C8F17; n = 2, 9), were successfully synthesized, and the effects of Rf, methylene chain length (n), and stereochemistry on their monolayer behaviors were studied. Critical micelle concentrations (CMC) of dl- and meso-2,3-bis[C4F9(CH2)9]-succinic acids were one order of magnitude smaller than that of the corresponding 1+1 type surfactant, C4F9(CH2)9COOH. From surface pressure-area (π-A) measurements, the lift-off areas of the geminis were found to decrease in the order C4F9 ≥ C6F13 > C8F17, regardless of methylene chain length and stereochemistry. The zero-pressure molecular areas of the geminis were twice those of the corresponding 1+1 type surfactants. Based on Gibbs compression modulus analysis, it was clarified that 2,3-bis[C8F17(CH2)n]-succinic gemini with short methylene chains (n = 2) would form more rigid monolayers than those having long methylene chains (n = 9). Unlike for 2,3-bis(alkyl)-succinic acids, the effects of stereochemistry on the monolayer behavior of semifluoroalkylated geminis were small.

  9. Different thermal unfolding pathways of catalase in the presence of cationic surfactants.

    Science.gov (United States)

    Blanco, Elena; Ruso, Juan M; Prieto, Gerardo; Sarmiento, Félix

    2007-03-01

    In this paper we have corroborated the usefulness of spectroscopic techniques, such as UV-visible, in the study and thermodynamic characterization of the thermal unfolding of catalase as a function of the concentration and alkyl chain length of n-alkyltrimethylammonium bromides (CnTAB, n = 8, 10, and 12). For this reason, a thermodynamic model was used which included experimental data corresponding to the pre- and posttransition into the observable transition. It has been found that n-alkyltrimethylammonium bromides play two opposite roles in the folding and stability of catalase. They act as a structure stabilizer at a low molar concentration and as a destabilizer at a higher concentration. The maximum of the unfolding temperature has been found to decrease with the alkyl chain. The reason for this difference has been suggested to be the side chains involved. In the presence of C8TAB and C10TAB, Gibbs energies of unfolding (DeltaG(T)) decrease with concentration, whereas for C12TAB an increase has been observed. These findings can be explained by the fact that when differences in the hydrophobic nature of the surfactants exist, different pathways of unfolding may occur. Also, the presence of surfactants has been observed to affect the cold denaturation of catalase. Thermodynamic results suggest that the thermal denaturation of catalase in the presence of n-alkyltrimethylammonium bromides is a perfect transition between two states.

  10. Modification of the activity of an a-amylase from Bacillus licheniformis by several surfactants

    OpenAIRE

    2006-01-01

    The influence of different commercial surfactants on the enzymatic activity of a commercial ??-amylase from Bacillus licheniformis (Termamyl 300 L) has been studied. As non-ionic surfactants, alkyl polyglycosides (Glucopon?? 215, Glucopon?? 600 and Glucopon?? 650) were studied, as were fatty alcohol ethoxylates (Findet 1214N/23 and Findet 10/15), and nonyl phenol ethoxylate (Findet 9Q/21.5NF). Also, an anionic surfactant, linear alkyl benzene sulfonate (LAS) was assayed. In general, none of t...

  11. THE EFFECT OF CHARGE AND CHEMICAL STRUCTURE OF CATIONIC SURFACTANTS ON LASER TONER AGGLOMERATION UNDER ALKALINE PULPING CONDITIONS

    Directory of Open Access Journals (Sweden)

    Jie Jiang,

    2012-02-01

    Full Text Available Laboratory-scale agglomeration experiments followed by image analysis were used to evaluate the effectiveness of different cationic surfactants on the 1-octadecanol agglomeration of a negatively charged laser toner. Various types of surfactants with different geometric structures were investigated. It was found that this toner became agglomerated under neutral pulping conditions, but it did not agglomerate under alkaline conditions at all. A small amount of the cationic surfactant compensated for the agglomeration disruption caused by the negative surface charge of the toner and made this toner agglomerate very well. These cationic surfactants consist of a chemical structure of C12 to C18 saturated alkyl hydrophobic chains. The positive charge of these surfactants played the major role in alleviating agglomeration disruption. Additionally, an extra phenol group on these surfactants contributed only minor advantages for toner agglomeration in the presence of 1-octadecanol. The best co-agglomeration performance occurred within a very narrow range of similar total positive charge densities based on the total toner weight. It was also found that this positive charge effect could not be applied to the chemical compounds of high molecular weight polymeric materials.

  12. Surfactants at the Design Limit.

    Science.gov (United States)

    Czajka, Adam; Hazell, Gavin; Eastoe, Julian

    2015-08-04

    This article analyzes how the individual structural elements of surfactant molecules affect surface properties, in particular, the point of reference defined by the limiting surface tension at the aqueous cmc, γcmc. Particular emphasis is given to how the chemical nature and structure of the hydrophobic tails influence γcmc. By comparing the three different classes of surfactants, fluorocarbon, silicone, and hydrocarbon, a generalized surface packing index is introduced which is independent of the chemical nature of the surfactants. This parameter ϕcmc represents the volume fraction of surfactant chain fragments in a surface film at the aqueous cmc. It is shown that ϕcmc is a useful index for understanding the limiting surface tension of surfactants and can be useful for designing new superefficient surfactants.

  13. Methotrexate intercalated layered double hydroxides with the mediation of surfactants: Mechanism exploration and bioassay study

    Energy Technology Data Exchange (ETDEWEB)

    Dai, Chao-Fan; Tian, De-Ying; Li, Shu-Ping, E-mail: lishuping@njnu.edu.cn; Li, Xiao-Dong

    2015-12-01

    Methotrexatum intercalated layered double hydroxides (MTX/LDHs) hybrids were synthesized by the co-precipitation method and three kinds of nonionic surfactants with different hydrocarbon chain lengths were used. The resulting hybrids were then characterized by X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy and transmission electron microscopy (TEM). XRD and FTIR investigations manifest the successful intercalation of MTX anions into the interlayer of LDHs. TEM graphs indicate that the morphology of the hybrids changes with the variation of the chain length of the surfactants, i.e., the particles synthesized using polyethylene glycol (PEG-7) present regular disc morphology with good monodispersity, while samples with the mediation of alkyl polyglycoside (APG-14) are heavily aggregated and samples with the addition of polyvinylpyrrolidone (PVP-10) exhibit irregular branches. Furthermore, the release and bioassay experiments show that monodisperse MTX/LDHs present good controlled-release and are more efficient in the suppression of the tumor cells. - Highlights: • Surfactants could be used to modify the dispersing state of MTX/LDHs hybrids. • Surfactants have great effect on the morphology of MTX/LDHs hybrids. • MTX/LDHs with good monodisperse degree are more efficient in the suppression of the tumor cells.

  14. Interfacial assignment of branched-alkyl benzene sulfonates: A molecular simulation

    Science.gov (United States)

    Liu, Zi-Yu; Wei, Ning; Wang, Ce; Zhou, He; Zhang, Lei; Liao, Qi; Zhang, Lu

    2015-11-01

    A molecular dynamics simulation was conducted to analyze orientations of sodium branched-alkyl benzene sulfonates molecules at nonane/water interface, which is helpful to design optimal surfactant structures to achieve ultralow interfacial tension (IFT). Through the two dimensional density profiles, monolayer collapses are found when surfactant concentration continues to increase. Thus the precise scope of monolayer is certain and orientation can be analyzed. Based on the simulated results, we verdict the interfacial assignment of branched-alkyl benzene sulfonates at the oil-water interface, and discuss the effect of hydrophobic tail structure on surfactant assignment. Bigger hydrophobic size can slow the change rate of surfactant occupied area as steric hindrance, and surfactant meta hydrophobic tails have a stronger tendency to stretch to the oil phase below the collapsed concentration. Furthermore, an interfacial model with reference to collapse, increasing steric hindrance and charge repulsive force between interfacial surfactant molecules, responsible for effecting of surfactant concentration and structure has been supposed.

  15. Corrosion inhibition of mild steel by amphoteric surfactants derived from aspartic acid

    Energy Technology Data Exchange (ETDEWEB)

    Morsi, M.S. (Cairo Univ., Faculty of Science, Chemistry Dept., Giza (Egypt)); Barakat, Y.F. (Cairo Univ., Faculty of Science, Chemistry Dept., Giza (Egypt)); El-Sheikh, R. (Cairo Univ., Faculty of Science, Chemistry Dept., Giza (Egypt)); Hassan, A.M. (Cairo Univ., Faculty of Science, Chemistry Dept., Giza (Egypt)); Baraka, A. (Cairo Univ., Faculty of Science, Chemistry Dept., Giza (Egypt))

    1993-07-01

    The inhibition of mild steel corrosion in 0.5 M HCl solution by amphoteric surfactants (which contain both an anionic and a cationic moiety in the same molecule) of general formula: NH[sub 2]-(CH[sub 2])[sub 2]-NH-CH(COOH)-CH[sub 2]-CO-NHR (R alkyl group of C[sub 10,] [sub 11,] [sub 12,] [sub 13,] [sub 15,] [sub and] [sub 17]) is shown to confirm Langmuir's absorption isotherms. At a given concentration of surfactants, the inhibiting action increases with the increase of carbon chain length. The influence of both inductive and steric hindrance effects of methylene groups in -R on the inhibition efficiency has also been mentioned. (orig.)

  16. Thermodynamic Studies of Aqueous m-s-m Gemini Surfactant Systems.

    Science.gov (United States)

    Wettig, S. D.; Verrall, R. E.

    2001-03-15

    The specific conductance, surface tension, and apparent molar volume properties of aqueous solutions of two series of m-s-m gemini surfactants-one having a constant spacer s(=3) with m=8, 10, 12, and 16 and the other having a constant alkyl chain length m(=12) with variable spacer length 2bolaform cation. Poor agreement was obtained with the first method, while good agreement was obtained with the second. The observed variation in the volume change due to micelle formation, DeltaV(φ,M), is consistent with variations in the head group area and critical micelle concentrations and can be rationalized in terms of the location of the spacer-either at the micelle/water interface, or in the micelle interior. Results obtained for the 12-φ-12 surfactant indicate that rigidity of the spacer has no measurable effect on the micellization process for such a short spacerlength. Copyright 2001 Academic Press.

  17. In situ Fourier transform-infrared internal reflection spectroscopic analysis of hydrocarbon chain ordering of surfactants adsorbed at mineral oxide surfaces

    Science.gov (United States)

    Cross, William Murray

    The adsorption of surfactants at mineral oxide surfaces was investigated by in situ Fourier transform infrared internal reflection spectroscopy (FT-IR/IRS), and contact angle goniometry. FT-IR/IRS was used to determine both adsorption isotherms and the enthalpy of adsorption. Furthermore, the conformation and orientation of the hydrocarbon chain of SDS adsorbed at a sapphire internal reflection element (IRE) were determined. Contact angle goniometry was used to measure the effect of the surface phase of the surfactant on the hydrophobic character of sapphire surfaces in aqueous solutions. For SDS adsorbed by sapphire, in situ FT-IR/IRS experiments indicate that a surface phase transition occurs at an adsorption density of 2 to 3 x 10-10 mol/cm2 for both pD 2.9 and 6.9. This transition is characterized by a two to four wavenumber shift in the position of the asymmetric -CH2 stretching band. Based on solution spectroscopy studies, the surface phase was found to be similar to solution phase micelles and liquid crystals for adsorption densities less than the adsorption density of the surface phase transition. Whereas for adsorption densities in excess of the adsorption density of the surface phase transition, the surface phase resembled a solution phase coagel species. It was also found that the contact angle of an air bubble at the sapphire surface exhibited a sharp decrease at the adsorption density corresponding to the surface phase transition The effect of temperature on adsorption and phase behavior of SDS at the sapphire IRE surface was also determined. It was shown that a surface phase transition similar to that discussed occurred at approximately 298 K. The adsorption reaction was found to be exothermic, with a heat of adsorption of --1.3 kcal/mole for adsorption densities less than the adsorption density of the surface phase transition at 298 K and --4.1 kcal/mole for adsorption densities greater than the adsorption density of the surface phase transition

  18. Novel serine-based gemini surfactants as chemical permeation enhancers of local anesthetics: A comprehensive study on structure-activity relationships, molecular dynamics and dermal delivery.

    Science.gov (United States)

    Teixeira, Raquel S; Cova, Tânia F G G; Silva, Sérgio M C; Oliveira, Rita; do Vale, M Luísa C; Marques, Eduardo F; Pais, Alberto A C C; Veiga, Francisco J B

    2015-06-01

    This work aims at studying the efficacy of a series of novel biocompatible, serine-based surfactants as chemical permeation enhancers for two different local anesthetics, tetracaine and ropivacaine, combining an experimental and computational approach. The surfactants consist of gemini molecules structurally related, but with variations in headgroup charge (nonionic vs. cationic) and in the hydrocarbon chain lengths (main and spacer chains). In vitro permeation and molecular dynamics studies combined with cytotoxicity profiles were performed to investigate the permeation of both drugs, probe skin integrity, and rationalize the interactions at molecular level. Results show that these enhancers do not have significant deleterious effects on the skin structure and do not cause relevant changes on cell viability. Permeation across the skin is clearly improved using some of the selected serine-based gemini surfactants, namely the cationic ones with long alkyl chains and shorter spacer. This is noteworthy in the case of ropivacaine hydrochloride, which is not easily administered through the stratum corneum. Molecular dynamics results provide a mechanistic view of the surfactant action on lipid membranes that essentially corroborate the experimental observations. Overall, this study suggests the viability of these serine-based surfactants as suitable and promising delivery agents in pharmaceutical formulations.

  19. Effect of alkyl chain length on the interfacial strength of surgical sealants composed of hydrophobically-modified Alaska-pollock-derived gelatins and poly(ethylene)glycol-based four-armed crosslinker.

    Science.gov (United States)

    Mizuta, Ryo; Ito, Temmei; Taguchi, Tetsushi

    2016-10-01

    Surgical sealants are widely used clinically. Fibrin sealant is a commonly used sealant, but is ineffective under wet conditions during surgery. In this study, we developed surgical sealants composed of hydrophobically modified Alaska-pollock-derived gelatins (hm-ApGltns) with different alkyl chain lengths from C3 to C18 and a poly(ethylene)glycol-based 4-armed crosslinker (4S-PEG). The burst strength of the hm-ApGltns-based sealant was evaluated using a fresh porcine blood vessel and was found to increase with increasing alkyl chain length from 167±22 to 299±43mmHg when the substitution ratio of amino groups of ApGltn was around 10mol%. The maximum burst strength was observed when stearoyl-group modified ApGltn (Ste-ApGltn)/4S-PEG-based sealant was used, displaying 3-fold higher burst strength than the original ApGltn (Org-ApGltn)/4S-PEG sealant, and 10-fold higher than the commercial fibrin sealant. Ste-ApGltn/4S-PEG-based sealant was biodegraded in rat subcutaneous tissue within 8 weeks without severe inflammation. By molecular interaction analysis using surface plasmon resonance, the binding constant of Ste-ApGltn to fibronectin was found to be 9-fold higher than that of Org-ApGltn. Therefore, the developed sealant, in particular the Ste-ApGltn/4S-PEG-based sealant, has potential applications in the field of cardiovascular surgery as well as thoracic surgery. Copyright © 2016 Elsevier B.V. All rights reserved.

  20. BINDING ISOTHERMS SURFACTANT-PROTEINS

    Directory of Open Access Journals (Sweden)

    Elena Irina Moater

    2011-12-01

    Full Text Available The interactions between surfactants and proteins shows some similarities with interactions between surfactants and polymers, but the hydrophobic amphoteric nature of proteins and their secondary and tertiary structure components make them different from conventional polymer systems. Many studies from the past about surfactant - proteins bonding used the dialysis techniques. Other techniques used to determine the binding isotherm, included ultrafiltration, ultracentrifugation, potentiometry, ion-selective electrode method and surface tension. High affinity isotherms which are typical of an anionic surfactant - protein bonding, exhibit an initial increase steep followed by a slow growth region and then a vertical growth above a certain concentration. This isotherm is typical of ionic surfactant to protein binding. Often the high affinity initial bond appears at very low concentrations of surfactant and therefore in some protein-surfactant systems, the exact shape of the isotherm in this region may be missing. The surfactant - protein binding is influenced by a number of variables such as the nature and chain length of surfactant, pH, ionic strength, temperature, nature of this protein and additives.

  1. New hydrophilic interaction/reversed-phase mixed-mode stationary phase and its application for analysis of nonionic ethoxylated surfactants.

    Science.gov (United States)

    Liu, Xiaodong; Pohl, Christopher

    2008-05-16

    We have developed a new stationary phase that combines both hydrophilic interaction and reversed-phase characteristics. The new phase is based on high-purity, porous and spherical silica gel functionalized with a silyl ligand consisting of both hydrophilic and hydrophobic functionalities. This phase can be operated in both HILIC mode (high organic solvent) and RPLC mode (low organic solvent). An optimal balance of hydrophilic and hydrophobic moieties on the silica surface provides unique chromatographic properties that make it useful for determination of alkyl chain distribution and degree of ethoxylation (EO number) of nonionic ethoxylated surfactants.

  2. Effects of alkyl parabens on plant pathogenic fungi.

    Science.gov (United States)

    Ito, Shinsaku; Yazawa, Satoru; Nakagawa, Yasutaka; Sasaki, Yasuyuki; Yajima, Shunsuke

    2015-04-15

    Alkyl parabens are used as antimicrobial preservatives in cosmetics, food, and pharmaceutical products. However, the mode of action of these chemicals has not been assessed thoroughly. In this study, we determined the effects of alkyl parabens on plant pathogenic fungi. All the fungi tested, were susceptible to parabens. The effect of linear alkyl parabens on plant pathogenic fungi was related to the length of the alkyl chain. In addition, the antifungal activity was correlated with the paraben-induced inhibition of oxygen consumption. The antifungal activity of linear alkyl parabens likely originates, at least in part, from their ability to inhibit the membrane respiratory chain, especially mitochondrial complex II. Additionally, we determined that some alkyl parabens inhibit Alternaria brassicicola infection of cabbage. Copyright © 2015 Elsevier Ltd. All rights reserved.

  3. Adsorption of alkyl-dimethyl-benzyl-ammonium chloride on differently pretreated nonwoven cotton substrate

    Science.gov (United States)

    The adsorption of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC), a cationic surfactant commonly employed as an antimicrobial agent, on greige, alkaline scoured, and bleached nonwoven cotton fabrics was investigated at varying surfactant concentrations and liquor ratios using UV-vis absorption spec...

  4. Degradation of surfactant-modified montmorillonites in HCl

    Energy Technology Data Exchange (ETDEWEB)

    Madejova, Jana, E-mail: jana.madejova@savba.sk [Institute of Inorganic Chemistry, SAS, Dubravska cesta 9, SK-845 36 Bratislava (Slovakia); Palkova, Helena, E-mail: helena.palkova@savba.sk [Institute of Inorganic Chemistry, SAS, Dubravska cesta 9, SK-845 36 Bratislava (Slovakia); Jankovic, Lubos, E-mail: lubos.jankovic@savba.sk [Institute of Inorganic Chemistry, SAS, Dubravska cesta 9, SK-845 36 Bratislava (Slovakia)

    2012-06-15

    The effect of surfactant size on the extent of montmorillonites decomposition in HCl was investigated. Na-SAz montmorillonite and tetraalkylammonium salts of alkyl-chains length increasing from methyl- Me{sub 4}N to pentyl- Pe{sub 4}N were used for organo-montmorillonites preparation. Decreasing intensity of d{sub 001} diffraction proved destruction of montmorillonite structure connected with gradual surfactant release. A shift of the SiO stretching band to 1097 cm{sup -1} confirmed formation of amorphous silica phase. A new band near 7315 cm{sup -1} corresponding to SiOH overtone revealed creation of protonated silica. This band was observed in the spectra of all acid-treated samples, also in those with minor decomposition of the structure. The size of the cations significantly affected decomposition of montmorillonites in HCl. The less stable were Na-SAz and Me{sub 4}N-SAz in which the content of octahedral atoms dropped to {approx}5% of their original values upon 8 h treatments. Et{sub 4}N-SAz and Pr{sub 4}N-SAz were slightly more resistant mainly at short times. Bu{sub 4}N-SAz and Pe{sub 4}N-SAz showed the least structural modifications, only 50% and 35% of octahedral atoms, respectively, were released into solution within 8 h treatments. This observation proves that bulky alkylammonium cations covering the inner and outer surfaces of montmorillonite prevent effectively the access of protons to the layers protecting the mineral from degradation in the acid. - Highlights: Black-Right-Pointing-Pointer Hybrid materials were prepared from montmorillonite and alkylammonium cations with short alkyl chains. Black-Right-Pointing-Pointer The effect of surfactant on organo-montmorillonites dissolution in HCl was studied. Black-Right-Pointing-Pointer With increasing size of cation the extent of montmorillonite decomposition decreased. Black-Right-Pointing-Pointer Bulky surfactants prevent the access of protons to the layers and thus protect montmorillonite from

  5. Biomimetic oligosaccharide and peptide surfactant polymers designed for cardiovascular biomaterials

    Science.gov (United States)

    Ruegsegger, Mark Andrew

    A common problem associated with cardiovascular devices is surface induced thrombosis initiated by the rapid, non-specific adsorption of plasma proteins onto the biomaterial surface. Control of the initial protein adsorption is crucial to achieve the desired longevity of the implanted biomaterial. The cell membrane glycocalyx acts as a non-thrombogenic interface through passive (dense oligosaccharide structures) and active (ligand/receptor interactions) mechanisms. This thesis is designed to investigate biomimicry of the cell glycocalyx to minimize non-specific protein adsorption and promote specific ligand/receptor interactions. Biomimetic macromolecules were designed through the molecular-scale engineering of polymer surfactants, utilizing a poly(vinyl amine) (PVAm) backbone to which hydrophilic (dextran, maltose, peptide) and hydrophobic alkyl (hexanoyl or hexanal) chains are simultaneously attached. The structure was controlled through the molar feed ratio of hydrophobic-to-hydrophilic groups, which also provided control of the solution and surface-active properties. To mimic passive properties, a series of oligomaltose surfactants were synthesized with increasing saccharide length (n = 2, 7, 15 where n is number of glucose units) to investigate the effect of coating height on protein adsorption. The surfactants were characterized by infra red (IR) and nuclear magnetic resonance (NMR) spectroscopies for structural properties and atomic force microscopy (AFM) and contact angle goniometry for surface activity. Protein adsorption under dynamic flow (5 dyn/cm2) was reduced by 85%--95% over the bare hydrophobic substrate; platelet adhesion dropped by ˜80% compared to glass. Peptide ligands were incorporated into the oligosaccharide surfactant to promote functional activity of the passive coating. The surfactants were synthesized to contain 0%, 25%, 50%, 75%, and 100% peptide ligand density and were stable on hydrophobic surfaces. The peptide surface density was

  6. Coarse-graining MARTINI model for molecular-dynamics simulations of the wetting properties of graphitic surfaces with non-ionic, long-chain and T-shaped surfactants

    CERN Document Server

    Sergi, Danilo; Ortona, Alberto

    2012-01-01

    We report on a molecular dynamics investigation of the wetting properties of graphitic surfaces by various solutions at concentrations 1-8 wt% of commercially available non-ionic surfactants with long hydrophilic chains, linear or T-shaped. These are surfactants of length up to 160 [\\AA]. It turns out that molecular dynamics simulations of such systems ask for a number of solvent particles that can be reached without seriously compromising computational efficiency only by employing a coarse-grained model. The MARTINI force field with polarizable water offers a framework particularly suited for our problem. In general, its advantages over other coarse-grained models are the possibility to explore faster long time scales and the wider range of applicability. Although the accuracy is sometimes put under question, the results for the wetting properties by pure water are in good agreement with those for the corresponding atomistic systems and theoretical predictions. On the other hand, the bulk properties of vario...

  7. Solid-State Organization and Ambipolar Field-Effect Transistors of Benzothiadiazole-Cyclopentadithiophene Copolymer with Long Branched Alkyl Side Chains

    Directory of Open Access Journals (Sweden)

    Martin Baumgarten

    2013-06-01

    Full Text Available The solid-state organization of a benzothiadiazole-cyclopentadithiophene copolymer with long, branched decyl-tetradecyl side chains (CDT-BTZ-C14,10 is investigated. The C14,10 substituents are sterically demanding and increase the π-stacking distance to 0.40 nm from 0.37 nm for the same polymer with linear hexadecyls (C16. Despite the bulkiness, the C14,10 side chains tend to crystallize, leading to a small chain-to-chain distance between lamellae stacks and to a crystal-like microstructure in the thin film. Interestingly, field-effect transistors based on solution processed layers of CDT-BTZ-C14,10 show ambipolar behavior in contrast to CDT-BTZ-C16 with linear side chains, for which hole transport was previously observed. Due to the increased π-stacking distance, the mobilities are only 6 × 10−4 cm²/Vs for electrons and 6 × 10−5 cm²/Vs for holes, while CDT-BTZ-C16 leads to values up to 5.5 cm²/Vs. The ambipolarity is attributed to a lateral shift between stacked backbones provoked by the bulky C14,10 side chains. This reorganization is supposed to change the transfer integrals between the C16 and C14,10 substituted polymers. This work shows that the electronic behavior in devices of one single conjugated polymer (in this case CDT-BTZ can be controlled by the right choice of the substituents to place the backbones in the desired packing.

  8. D-glucose derived novel gemini surfactants: synthesis and study of their surface properties, interaction with DNA, and cytotoxicity.

    Science.gov (United States)

    Kumar, Vikash; Chatterjee, Amrita; Kumar, Nupur; Ganguly, Anasuya; Chakraborty, Indranil; Banerjee, Mainak

    2014-10-09

    Four new D-glucose derived m-s-m type gemini surfactants with variable spacer and tail length have been synthesized by a simple and efficient synthetic methodology utilizing the free C-3 hydroxy group of diisopropylidene glucose. The synthetic route to these gemini surfactants with a quaternary ammonium group as polar head group involves a sequence of simple reactions including alkylation, imine formation, quaternization of amine etc. The surface properties of the new geminis were evaluated by surface tension and conductivity measurements. These gemini surfactants showed low cytotoxicity by MTT assay on HeLa cell line. The DNA binding capabilities of these surfactants were determined by agarose gel electrophoresis, fluorescence titration, and DLS experiments. The preliminary studies by agarose gel electrophoresis indicated chain length dependent DNA binding abilities, further supported by ethidium bromide exclusion experiments. Two of the D-glucose derived gemini surfactants showed effective binding with pET-28a plasmid DNA (pDNA) at relatively low N/P ratio (i.e., cationic nitrogen/DNA phosphate molar ratio).

  9. Aqueous foam surfactants for geothermal drilling fluids: 1. Screening

    Energy Technology Data Exchange (ETDEWEB)

    Rand, P.B.

    1980-01-01

    Aqueous foam is a promising drilling fluid for geothermal wells because it will minimize damage to the producing formation and would eliminate the erosion problems of air drilling. Successful use of aqueous foam will require a high foaming surfactant which will: (1) be chemically stable in the harsh thermal and chemical environment, and (2) form stable foams at high temperatures and pressures. The procedures developed to generate and test aqueous foams and the effects of a 260/sup 0/C temperature cycle on aqueous surfactant solutions are presented. More than fifty selected surfactants were evaluated with representatives from the amphoteric, anionic, cationic, and nonionic classes included. Most surfactants were severely degraded by this temperature cycle; however, some showed excellent retention of their properties. The most promising surfactant types were the alkyl and alkyl aryl sulfonates and the ethoxylated nonionics.

  10. Behavior of cationic surfactants and short-chain alcohols in mixed surface layers at water-air and polymer-water interfaces with regard to polymer wettability II. Wettability of polymers.

    Science.gov (United States)

    Zdziennicka, Anna; Jańczuk, Bronisław

    2010-10-15

    The wettability of polytetrafluoroethylene (PTFE) and polymethylmethacrylate (PMMA) by aqueous solutions of cetyltrimethylammonium bromide (CTAB) mixtures with short-chain alcohols such as methanol, ethanol, and propanol, as well as for 1-hexadecylpyridinium bromide (CPyB) with the same alcohols, was studied on the basis of advancing contact-angle measurements by the sessile drop method over a wide range of alcohol and cationic surfactant concentrations where they can be present in solution in monomeric or aggregated form. It should be noted that the contact angles for aqueous solution mixtures of cationic surfactants with propanol on PTFE surfaces were measured earlier and presented in our previous paper. From the obtained contact-angle values the relationships between cos theta and surface tension of the solutions (gamma(LV)) and that between adhesion tension and gamma(LV) were considered. The relationship between the cos theta and the reciprocal of gamma(LV) was also discussed. From these relationships the critical surface tension of PTFE and PMMA wetting and the correlation between the adsorption of cationic surfactant and alcohol mixtures at water-air and polymer-water interfaces were deduced. On the basis of the contact angles and components and parameters of the surface tension of surfactants, alcohols, and polymers also the Gibbs and Guggenheim-Adam isotherm of adsorption and the effective concentration of alcohols and surfactants at polymer-water interfaces were calculated. Next, the work of adhesion of solution to polymer surface with regard to the surface monolayer composition was discussed. The analysis of the contact angles with regard to adsorption of surfactants and alcohols at polymer-water and water-air interfaces allowed us to conclude that the PTFE wetting depends only on the contribution of the acid-base interactions to the surface tension of aqueous solutions of cationic surfactant and alcohol mixtures, and the adhesion work of solution to its

  11. Determination of non-ionic polyethoxylated surfactants in wastewater and river water by mixed hemimicelle extraction and liquid chromatography-ion trap mass spectrometry.

    Science.gov (United States)

    Cantero, Manuel; Rubio, Soledad; Pérez-Bendito, Dolores

    2005-03-04

    The capability of hemimicelles-based solid phase extraction (SPE)/liquid chromatography/atmospheric pressure chemical ionisation in positive mode, ion trap mass spectrometry (LC/(APCl+-IT)-MS) for the concentration, separation and quantitation of non-ionic surfactants has been investigated. Concentration was based on the formation of mixed aggregates of analytes [alkylphenol ethoxylates (APE, octyl and nonyl) and alkyl ethoxylates (AE, C12-C16)] with the anionic surfactant sodium dodecyl sulphate (SDS) that is adsorbed on alumina. Parameters affecting SPE were investigated on the basis that hemimicelles are dynamic entities in equilibrium with the aqueous phase. The performance of ion trap mass spectrometry for MS and MS/MS quantitation of non-ionic homologues was assessed. Recoveries of analytes from wastewater influent and effluent and river water samples ranged between 91 and 98% and were found independent on the length of the alkyl chain under the optimised conditions. Anionic surfactants did not interfere to the levels found in environmental samples. The detection limits ranged between 14 and 111 ng/l for wastewater influent, 10 and 40 for wastewater effluent and 4 and 35 for river water, after concentration of 250, 500 and 750 ml of sample, respectively. The approach was applied to the determination of AE and APE in influent and effluent samples from four wastewater treatment plants and four river samples. The concentrations of individual non-ionic surfactants found ranged between 0.3 and 373 microg/l.

  12. Green Synthesis, Molecular Characterization and Associative Behavior of Some Gemini Surfactants without a Spacer Group

    Directory of Open Access Journals (Sweden)

    Eugenio Caponetti

    2013-04-01

    Full Text Available A series of new gemini surfactants without a spacer group, disodium 2,3-dialkyl-1,2,3,4-butanetetracarboxylates, were synthesized in a green chemistry context minimizing the use of organic solvents and applying microwaves (MW when activation energy was required. Once the desired architecture was confirmed by means of the nuclear magnetic resonance technique (1H-NMR, 1H-1H COSY for all the studied surfactants, the critical micellization concentration was determined by conductance measurements. The diffusion coefficient of micelles formed by the four compounds was characterized using pulsed field gradient (PFG-NMR. Diffusion coefficients were found to be dependent on the concentration and on the number of carbon atoms in the alkyl chain. The absence of the spacer group, peculiar to this new series of gemini surfactants, may confer relatively low flexibility to the molecules, with potential implications on the interfacial properties, namely on micellization. These gemini surfactants might have interesting applications in the preparation of composite materials, in nanotechnology, in gene transfection and mainly, due to the low CMCs, as new interesting ingredients of cosmetics and toiletries.

  13. Nanostructured poly(benzimidazole membranes by N-alkylation

    Directory of Open Access Journals (Sweden)

    J. Weber

    2014-01-01

    Full Text Available Modification of poly(benzimidazole (PBI by N-alkylation leads to polymers capable of undergoing microphase separation. Polymers with different amounts of C18 alkyl chains have been prepared. The polymers were analyzed by spectroscopy, thermal analysis, electron microscopy and X-ray scattering. The impact of the amount of alkyl chains on the observed microphase separation was analyzed. Membranes prepared from the polymers do show microphase separation, as evidenced by scattering experiments. While no clear morphology could be derived for the domains in the native state, evidence for the formation of lamellar morphologies upon doping with phosphoric acid is provided. Finally, the proton conductivity of alkyl-modified PBI is compared with that of pure PBI, showing that the introduction of alkyl side chains does not result in significant conductivity changes.

  14. Gemini alkyldeoxy-D-glucitolammonium salts as modern surfactants and microbiocides: synthesis, antimicrobial and surface activity, biodegradation.

    Science.gov (United States)

    Brycki, Bogumił; Szulc, Adrianna

    2014-01-01

    Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-α,ω-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides), a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and (1)H and (13)C NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.

  15. Gemini alkyldeoxy-D-glucitolammonium salts as modern surfactants and microbiocides: synthesis, antimicrobial and surface activity, biodegradation.

    Directory of Open Access Journals (Sweden)

    Bogumił Brycki

    Full Text Available Dimeric quaternary alkylammonium salts possess a favourable surface and antimicrobial activity. In this paper we describe synthesis, spectroscopic analysis, surface and antimicrobial activity as well as biodegradability of polymethylene-α,ω-bis(N,N-dialkyl-N-deoxy-D-glucitolammonium iodides, a new group of dimeric quaternary ammonium salts. This new group of gemini surfactants can be produced from chemicals which come from renewable sources. The structure of products has been determined by the FTIR and (1H and (13C NMR spectroscopy. The biodegradability, surface activity and antimicrobial efficacy against Escherichia coli, Staphylococcus aureus, Candida albicans, Aspergillus niger and Penicillium chrysogenum were determined. The influence of the number of alkyl chains and their lengths on surface and antimicrobial properties has been shown. In general, dimeric quaternary alkyldeoxy-D-glucitolammonium salts with long alkyl substituents show favourable surface properties and an excellent antimicrobial activity.

  16. Mechanisms of Neutral and Anionic Surfactant Sorption to Solid-Phase Microextraction Fibers.

    Science.gov (United States)

    Haftka, Joris J-H; Hammer, Jort; Hermens, Joop L M

    2015-09-15

    Octanol-water partitioning (Kow) is considered a key parameter for hydrophobicity and is often applied in the prediction of the environmental fate and exposure of neutral organic compounds. However, surfactants can create difficulties in the determination of Kow because of emulsification of both water and octanol phases. Moreover, not only is sorption behavior of ionic surfactants related to hydrophobicity, but also other interactions are relevant in sorption processes. A different approach to develop parameters that can be applied in predictive modeling of the fate of surfactants in the environment is therefore required. Distribution between solid-phase microextraction (SPME) fibers and water was used in this study to measure the affinity of surfactants to a hydrophobic phase. Fiber-water sorption coefficients of alcohol ethoxylates, alkyl carboxylates, alkyl sulfates, and alkyl sulfonates were determined at pH 7 by equilibration of the test analytes between fiber and water. Distribution between fiber and water of anionic compounds with pKa ∼ 5 (i.e., alkyl carboxylates) was dominated by the neutral fraction. Anionic surfactants with pKa ≤ 2 (i.e., alkyl sulfates and alkyl sulfonates) showed strong nonlinear distribution to the fiber. The fiber-water sorption coefficients for alcohol ethoxylates and alkyl sulfates showed a linear trend with bioconcentration factors from the literature. Fiber-water sorption coefficients are promising as a parameter to study the effects of hydrophobicity and other potential interactions on sorption behavior of neutral and anionic surfactants.

  17. A new approach to the side chain formation of 24-alkyl-22-hydroxy steroids: application to the preparation of early brassinolide biosynthetic precursors.

    Science.gov (United States)

    Hurski, Alaksiej L; Zhabinskii, Vladimir N; Khripach, Vladimir A

    2012-06-01

    A new synthetic route to 22S-hydroxy-24R-methyl steroids has been developed and applied for the preparation of cathasterone, (22S)-hydroxycampesterol, and 6-deoxocathasterone, which are precursors in the early stages of the biosynthesis of brassinolide. The construction of the steroid side chain with the correct stereochemistry at C-24 is based on the use of Claisen rearrangement. The introduction of the 22-hydroxyl group has been achieved by epoxidation of the Δ(22)-double bond, nucleophilic opening of the intermediate mesyl epoxide with sodium sulfide, and desulfurization of the formed tetrahydrothiophenes with Raney nickel.

  18. Aggregation of sulfosuccinate surfactants in water

    Energy Technology Data Exchange (ETDEWEB)

    Magid, L.J.; Daus, K.A.; Butler, P.D.; Quincy, R.B.

    1983-12-22

    The aggregation of sodium di-n-alkyl sulfosuccinates in water (H/sub 2/O and D/sub 2/O at 45/sup 0/C) has been investigated. A self-consistent picture of the dependence of sodium ion binding on surfactant concentration is obtained from emf measurements, conductimetry, and small-angle neutron scattering (SANS) measurements. The concentration dependence of the micellar agregation number for the sulfosuccinates and related double-tailed surfactants depends markedly on surfactant solubility. A sphere-to-disk transition in micellar shape, which might have been expected as a precursor to formation of a lamellar mesophase, was not observed as the surfactant concentration was increased. 8 figures, 2 tables.

  19. Thermodynamic properties of micellization of Sulfobetaine-type Zwitterionic Gemini Surfactants in aqueous solutions--a free energy perturbation study.

    Science.gov (United States)

    Liu, Guoyu; Gu, Daming; Liu, Haiyan; Ding, Wei; Luan, Huoxin; Lou, Yanmin

    2012-06-01

    In this article, the validity and accuracy of the free energy perturbation (FEP) model used in a previous article for ionic liquid-type Gemini imidazolium surfactants (ILGISs) is further evaluated by using it to model the Enthalpy-entropy compensation of Sulfobetaine-type Zwitterionic Gemini Surfactants (SZGSs), with different carbon atoms of the hydrophobic group or the spacer chain length, in aqueous solutions. In the FEP model, the Gibbs free energy contributions to the driving force for micelle formation are computed using hydration data obtained from molecular dynamics simulations. According to the pseudo-phase separation model, the thermodynamic properties of micellization in aqueous solutions for SZGS were discussed. The results show that the micellization of SZGS in aqueous solutions is a spontaneous and entropy-driven process. It is linearly Enthalpy-entropy compensated and different from the micelle formation of ILGIS but similar to anionic surfactants. The compensation temperature was found to be (302±3)K which was lower than ILGIS. As the temperature rises, the micellization is easy initially but then becomes difficult with the unusual changes of enthalpy values from positive to negative. The contribution of entropy change to the micellization tends to decrease but the contribution of enthalpy change tends to increase. In particular, as the number carbon atoms in the alkyl chains and spacer chains are increased, the thermodynamic favorability and stability of the micelles both increase.

  20. Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution.

    Science.gov (United States)

    Garcia, M Teresa; Ribosa, Isabel; Perez, Lourdes; Manresa, Angeles; Comelles, Francesc

    2014-11-01

    Surface active amide-functionalized ionic liquids (ILs) consisting of a long alkyl chain (C6C14) connected to a polar head group (methylimidazolium or pyridinium cation) via an amide functional group were synthesized and their thermal stability, micellar properties and antimicrobial activity in aqueous solution investigated. The incorporation of an amide group increased the thermal stability of the functionalized ionic liquids compared to simple alkyl chain substituted ionic liquids. The surface activity and aggregation behaviour in aqueous solution of amide-functionalized ionic liquids were examined by tensiometry, conductivity and spectrofluorimetry. Amide-functionalized ILs displayed surface activity and their critical micelle concentration (cmc) in aqueous media decreased with the elongation of the alkyl side chain as occurs for typical surfactants. Compared to non-functionalized ILs bearing the same alkyl chain, ionic liquids with an amide moiety possess higher surface activity (pC20) and lower cmc values. The introduction of an amide group in the hydrophobic chain close to the polar head enhances adsorption at the air/water interface and micellization which could be attributed to the H-bonding in the headgroup region. The antimicrobial activity was evaluated against a panel of representative Gram-negative and Gram-positive bacteria and fungi. Amide-functionalized ILs with more than eight carbon atoms in the side chain showed broad antimicrobial activity. Antibacterial activities were found to increase with the alkyl chain length being the C12 homologous the most effective antimicrobial agents. The introduction of an amide group enhanced significantly the antifungal activity as compared to non-functionalized ILs.

  1. Surface hydrophobization by electrostatic deposition of hydrophobically modified poly(acrylates) and their complexes with surfactants

    Science.gov (United States)

    Gîfu, Ioana Cătălina; Maxim, Monica Elisabeta; Iovescu, Alina; Simion, Elena Livia; Aricov, Ludmila; Anastasescu, Mihai; Munteanu, Cornel; Anghel, Dan-Florin

    2016-05-01

    The present study demonstrates the hydrophobic effect of poly(electrolyte) multilayer films when they are alkyl-grafted and complexed or not with surfactants. For this purpose, sodium hydrophobically modified poly(acrylates) (PACnNa, n = 10, 18) or their anionic complexes with alkyltrimethylammonium bromides (CxTAB, x = 10, 12, 14, 18), and the cationic poly(diallyldimethyldiammonium chloride) (PDDAMAC) are assembled by layer-by-layer deposition on a glass substrate. Contact angle (CA) measurements reveal that films constructed with PACnNa-CxTAB/PDADMAC are superior water repellants than those of PACnNa/PDADMAC. For example, the highest CA is obtained for the PAC18Na-C18TAB/PDADMAC. Moreover, it has been observed that the CA increases with the alkyl chain length of PACnNa and of surfactant. The film roughness and thickness have the same trend as wettability. Thinner and less coarse films are obtained by NaCl addition, as witnessed by SEM and AFM.

  2. Effects of alkyl polyglycoside (APG) on Bombyx mori silk degumming and the mechanical properties of silk fibroin fibre.

    Science.gov (United States)

    Wang, Fei; Zhang, Yu-Qing

    2017-05-01

    Alkyl polyglycoside (APG), a nonionic surfactant, is often considered to be a green surfactant and is synthesized using glucose and long chain fatty alcohols. It is used as a degumming agent of Bombyx mori silk fibre in this study for the first time. We studied APG systematically in comparison to the traditional degumming methods, such as aqueous solutions of sodium carbonate (Na2CO3) and neutral soap (NS). After repeatedly boiling silk fibres in an aqueous solution of 0.25% APG three times for 30min and using a bath ratio of 1:90-120 (g/mL), sericin was completely removed from the fibre. SDS-PAGE showed that the degumming in APG did not induce an evident breakage of the silk fibroin peptide chains, including the light chain and P25 protein. The tensile properties, thermal analysis, and scanning electron microscopic (SEM) observation of the degummed fibroin fibre all show that APG is a degumming agent similar to NS and far superior to Na2CO3. These results indicate that APG is an environment-friendly silk degumming/refining agent in the silk textile industry and in the manufacture of silk floss quilts. Copyright © 2017 Elsevier B.V. All rights reserved.

  3. Alkylation of Chitosan as Nerve Conduit Biomaterial

    Institute of Scientific and Technical Information of China (English)

    邓劲光; 公衍道; 程明愚; 赵南明; 张秀芳

    2002-01-01

    Chitosan under physiological conditions is a degradable and biocompatible biomaterial with a wide variety of useful physicochemical properties. However, as a nerve conduit biomaterial, its solubility was very low, so chitosan was modified chemically to enhance its solubility. The free amino groups of long molecular chains in chitosan are responsible for its solubility, and the solubility could be adjusted by controlling the free amidogen capacity with N-alkylation. The results show that the solubility of N-alkylation chitosan is increased to 10%, which is an increase of 500%.

  4. Inhibitory Activities of Alkyl Syringates and Related Compounds on Aflatoxin Production

    Directory of Open Access Journals (Sweden)

    Tomohiro Furukawa

    2016-06-01

    Full Text Available Inhibitors of aflatoxin production of aflatoxigenic fungi are useful for preventing aflatoxin contamination in crops. As methyl syringate weakly inhibits aflatoxin production, aflatoxin production inhibitory activities of additional alkyl syringates with alkyl chains from ethyl to octyl were examined. Inhibitory activity toward aflatoxin production of Aspergillus flavus became stronger as the length of the alkyl chains on the esters became longer. Pentyl, hexyl, heptyl, and octyl syringates showed strong activity at 0.05 mM. Heptyl and octyl parabens, and octyl gallate also inhibited aflatoxin production as strongly as octyl syringate. Alkyl parabens and alkyl gallates inhibit the complex II activity of the mitochondrial respiration chain; thus, whether alkyl syringates inhibit complex II activity was examined. Inhibitory activities of alkyl syringates toward complex II also became stronger as the length of the alkyl chains increased. The complex II inhibitory activity of octyl syringate was comparable to that of octyl paraben and octyl gallate. These results suggest that alkyl syringates, alkyl parabens, and alkyl gallates, including commonly used food additives, are useful for aflatoxin control.

  5. Inhibitory Activities of Alkyl Syringates and Related Compounds on Aflatoxin Production

    Science.gov (United States)

    Furukawa, Tomohiro; Iimura, Kurin; Kimura, Taichi; Yamamoto, Toshiyoshi; Sakuda, Shohei

    2016-01-01

    Inhibitors of aflatoxin production of aflatoxigenic fungi are useful for preventing aflatoxin contamination in crops. As methyl syringate weakly inhibits aflatoxin production, aflatoxin production inhibitory activities of additional alkyl syringates with alkyl chains from ethyl to octyl were examined. Inhibitory activity toward aflatoxin production of Aspergillus flavus became stronger as the length of the alkyl chains on the esters became longer. Pentyl, hexyl, heptyl, and octyl syringates showed strong activity at 0.05 mM. Heptyl and octyl parabens, and octyl gallate also inhibited aflatoxin production as strongly as octyl syringate. Alkyl parabens and alkyl gallates inhibit the complex II activity of the mitochondrial respiration chain; thus, whether alkyl syringates inhibit complex II activity was examined. Inhibitory activities of alkyl syringates toward complex II also became stronger as the length of the alkyl chains increased. The complex II inhibitory activity of octyl syringate was comparable to that of octyl paraben and octyl gallate. These results suggest that alkyl syringates, alkyl parabens, and alkyl gallates, including commonly used food additives, are useful for aflatoxin control. PMID:27338472

  6. Cationic versus anionic surfactant in tuning the structure and interaction of nanoparticle, protein, and surfactant complexes.

    Science.gov (United States)

    Mehan, Sumit; Aswal, Vinod K; Kohlbrecher, Joachim

    2014-08-26

    The structure and interaction in complexes of anionic Ludox HS40 silica nanoparticle, anionic bovine serum albumin (BSA) protein, and cationic dodecyl trimethylammonium bromide (DTAB) surfactant have been studied using small-angle neutron scattering (SANS). The results are compared with similar complexes having anionic sodium dodecyl sulfate (SDS) surfactant (Mehan, S; Chinchalikar, A. J.; Kumar, S.; Aswal, V. K.; Schweins, R. Langmuir 2013, 29, 11290). In both cases (DTAB and SDS), the structure in nanoparticle-protein-surfactant complexes is predominantly determined by the interactions of the individual two-component systems. The nanoparticle-surfactant (mediated through protein-surfactant complex) and protein-surfactant interactions for DTAB, but nanoparticle-protein (mediated through protein-surfactant complex) and protein-surfactant interactions for SDS, are found to be responsible for the resultant structure of nanoparticle-protein-surfactant complexes. Irrespective of the charge on the surfactant, the cooperative binding of surfactant with protein leads to micellelike clusters of surfactant formed along the unfolded protein chain. The adsorption of these protein-surfactant complexes for DTAB on oppositely charged nanoparticles gives rise to the protein-surfactant complex-mediated aggregation of nanoparticles (similar to that of DTAB surfactant). It is unlike that of depletion-induced aggregation of nanoparticles with nonadsorption of protein-surfactant complexes for SDS in similarly charged nanoparticle systems (similar to that of protein alone). The modifications in nanoparticle aggregation as well as unfolding of protein in these systems as compared to the corresponding two-component systems have also been examined by selectively contrast matching the constituents.

  7. Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants

    Energy Technology Data Exchange (ETDEWEB)

    Geng, Xiang F., E-mail: gengxiangfei1988111@126.com [School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500 (China); State Key Laboratory of Oil and Gas Reservoir Geology and Exploration, Southwest Petroleum University, Chengdu 610500 (China); Hu, Xing Q.; Xia, Ji J. [School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500 (China); State Key Laboratory of Oil and Gas Reservoir Geology and Exploration, Southwest Petroleum University, Chengdu 610500 (China); Jia, Xue C. [Institute of Resources and Environmental, Southwest Petroleum University, Chengdu 610500 (China)

    2013-04-15

    A series of novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants of 1,2-bis[N-ethyl-N-(2-hydroxyl-3-sulfopropyl)-alkylammonium] alkyl betaines (DBA{sub s–n}, where s and n represent the spacer length of 2, 4 and 6 and the hydrocarbon chain length of 8, 12, 14, 16 and 18, respectively) were synthesized by reacting alkylamine with sodium 3-chloro-2-hydroxypropanesulfonate (the alternative sulphonated agent), followed by the reactions with a,ω-dibromoalkyl and then ethyl bromide. Their adsorption and aggregation properties were investigated by means of equilibrium surface tension, dynamic light-scattering (DLS) and transmission electron microscopy (TEM). DBA{sub s–n} gemini surfactants showed excellent surface activities and packed tightly at the interface. For example, the minimum CMC value for DBA{sub s–n} series was of the order of 10{sup −5} M and the surface tension of water can be decreased as low as 22.2 mN/m. It was also found that the aggregates of DBA{sub s–n} solutions were significantly dependent on their hydrocarbon chain lengths. The aggregates changed from vesicles to entangled fiber-like micelles as the chain length increased from dodecyl to tetradecyl.

  8. Synthesis and surface activities of a novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants

    Science.gov (United States)

    Geng, Xiang F.; Hu, Xing Q.; Xia, Ji J.; Jia, Xue C.

    2013-04-01

    A series of novel di-hydroxyl-sulfate-betaine-type zwitterionic gemini surfactants of 1,2-bis[N-ethyl-N-(2-hydroxyl-3-sulfopropyl)-alkylammonium] alkyl betaines (DBAs-n, where s and n represent the spacer length of 2, 4 and 6 and the hydrocarbon chain length of 8, 12, 14, 16 and 18, respectively) were synthesized by reacting alkylamine with sodium 3-chloro-2-hydroxypropanesulfonate (the alternative sulphonated agent), followed by the reactions with а,ω-dibromoalkyl and then ethyl bromide. Their adsorption and aggregation properties were investigated by means of equilibrium surface tension, dynamic light-scattering (DLS) and transmission electron microscopy (TEM). DBAs-n gemini surfactants showed excellent surface activities and packed tightly at the interface. For example, the minimum CMC value for DBAs-n series was of the order of 10-5 M and the surface tension of water can be decreased as low as 22.2 mN/m. It was also found that the aggregates of DBAs-n solutions were significantly dependent on their hydrocarbon chain lengths. The aggregates changed from vesicles to entangled fiber-like micelles as the chain length increased from dodecyl to tetradecyl.

  9. Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water

    NARCIS (Netherlands)

    Schouten, Natasja; Ham, Louis G.J. van der; Euverink, Gert-Jan W.; Haan, André B. de

    2007-01-01

    Low-cost adsorbents were tested to remove anionic surfactants from laundry rinsing water to allow re-use of water. Adsorbents were selected corresponding to the different surfactant adsorption mechanisms. Equilibrium adsorption studies of linear alkyl benzene sulfonate (LAS) show that ionic interact

  10. Alkyl polyglycoside-sorbitan ester formulations for improved oil recovery

    Energy Technology Data Exchange (ETDEWEB)

    Wu, Y.; Iglauer, S.; Shuler, P.; Tang, Y. [Power Environmental Energy Research Institute (PEERI), Covina, CA (United States); Goddard, W.A. III [California Inst. of Technology, Pasadena, CA (US). Div. of Chemistry and Chemical Engineering, Materials and Process Simulation Center (MSC)

    2010-09-15

    We measured interfacial tensions (IFT) of aqueous alkyl polyglucoside (APG) systems formulated with sorbitan ester-type cosurfactants against n-octane. The study focused on low to ultra-low IFT systems which are relevant for enhanced oil recovery (EOR). In addition, we measured equilibrium adsorption concentrations of these surfactants and cosurfactants onto kaolinite clay, commonly found in oil reservoirs. We present one surfactant EOR laboratory flood experiment with one selected APG-sorbitan ester formulation with which we recovered 94% of initial oil in place (IOIP). (orig.)

  11. A Study on Alkyl Polyglycosides of the Starch

    Institute of Scientific and Technical Information of China (English)

    Wang Qing-ning; Li Chun-lei; Feng Hui-xia; Kang Wen-shu

    2004-01-01

    The alkyl polyglycosides (APG) is new type the surfactants that is made by regenerationresource of the starch and the grease, since the nineties of 20th century it is energetically exploited ininternational extent. APG not only good in surface activity, but also plenty on bubble, thin greasyand stabilization, there are good decontamination, compatibility, innocuity, not incitation and uniquefunction that organism decomposition of swiftness and downrightness, and so on.APG is to get production that loses one molecule water with half condensation aldehyde hydroxyand sebum alcohol hydroxy under acid catalysis. The production not is one simplicity compound, butis one of sugar polymerization degree, so it is mixture of the alkyl single glucoside, the alkyl twoglucoside and the alkyl three glucoside.Author synthesizes the surfactants of the alkyl polyglycosides, with the oleaster and potato starchand sebum alcohol, that was chosen to use duality system activator of plant acid and p-toluene-sulfoacid for the first time. The adoption way is that the lower alkyl polyglycosides is firstly formed byreaction of lower alcohol with starch then exchanged with high alcohol to obtain APG. The study isto make certain most technics condition, determining capillary tension and the pastern sheafdeepness of critical, calculating HLB value, determining construction by 1R.To synthesize principium:Peroration :[1]Duality system activator of plant acid and p-toluene-sulfo acid is compare idea activator that was the lower alkyl polyglycosides is firstly formed by reaction of lower alcohol with glucose then exchanged with high alcohol to obtain high alkyl polyglycosides. The advantage is that it overcomes agglomeration, there is reaction entirety, high of sugar transform ratio, reaction time short.[2]Most good reaction temperature is 90~ 170℃, the dosage of activator is 0.5%~0.9%, the mated ratio: The APG of glucose basic butane ratio starch is 5:1, the APG of potato starch basic glycol

  12. The Cloud Point of Alkyl Ethoxylates and Its Prediction with the Hydrophilic-Lipophilic Difference (HLD) Framework.

    Science.gov (United States)

    Zarate-Muñoz, Silvia; Boza Troncoso, Americo; Acosta, Edgar

    2015-11-10

    The hydrophobicity of surfactants has been described through different concepts used to guide the formulation of surfactant-water (SW) and surfactant-oil-water (SOW) systems. An integrated framework of hydrophobicity indicators could provide a complete tool for surfactant characterization, and insights on how their relationship may influence the overall phase behavior of the system. The hydrophilic-lipophilic difference (HLD) and the characteristic curvature (Cc) parameter, included in the HLD, have been shown to correlate with different hydrophobicity indicators including the hydrophilic-lipophilic balance (HLB), packing factor (Pf), phase inversion temperature (PIT), spontaneous curvature (Ho), surfactant partition (K(o-w)), and the critical micelle concentration (CMC). This work aims to investigate whether the HLD can further describe a concomitant hydrophobicity parameter, the cloud point (CP) of alkyl ethoxylates. After applying group contribution models to calculate the Cc of monodisperse (pure) nonionic alkyl ethoxylates, a linear correlation between the calculated Cc and the CP was observed for pure surfactants with 8 ethylene oxide (EO) units or less. Furthermore, using an apparent equivalent alkane carbon number (EACN) to represent the hydrophobicity of the micelle core, the HLD equation was capable of predicting cloud point temperatures of pure alkyl ethoxylates, typically within 5 °C. Polydisperse surfactants did not follow the linear CP-Cc correlation found for pure surfactants. After treating polydisperse samples using a liquid-liquid extraction procedure used to remove the most hydrophobic components in the mixture, the resulting treated surfactants fell in the correlation line of pure alkyl ethoxylates. A closer look at the partition behavior of these treated surfactants showed that their partition, Cc and cloud point are dominated by the most abundant ethoxymers in the treated surfactant. The HLD also predicted the cloud point depression of

  13. Diversifying the solid state and lyotropic phase behavior of nonionic urea-based surfactants.

    Science.gov (United States)

    Fong, Celesta; Wells, Darrell; Krodkiewska, Irena; Weerawardeena, Asoka; Booth, Jamie; Hartley, Patrick G; Drummond, Calum J

    2007-09-13

    The solid state and lyotropic phase behavior of 10 new nonionic urea-based surfactants has been characterized. The strong homo-urea interaction, which can prevent urea surfactants from forming lyotropic liquid crystalline phases, has been ameliorated through the use of isoprenoid hydrocarbon tails such as phytanyl (3,7,11,15-tetramethyl-hexadecyl) and hexahydrofarnesyl (3,7,11-trimethyl-dodecyl) or the oleyl chain (cis-octadec-9-enyl). Additionally, the urea head group was modified by attaching either a hydroxy alkyl (short chain alcohol) moiety to one of the nitrogens of the urea or by effectively "doubling" the urea head group by replacing it with a biuret head group. The solid state phase behavior, including the liquid crystal-isotropic liquid, polymorphic, and glass transitions, is interpreted in terms of molecular geometries and probable hydrogen-bonding interactions. Four of the modified urea surfactants displayed ordered lyotropic liquid crystalline phases that were stable in excess water at both room and physiological temperatures, namely, 1-(2-hydroxyethyl)-1-oleyl urea (oleyl 1,1-HEU) with a 1D lamellar phase (Lalpha), 1-(2-hydroxyethyl)-3-phytanyl urea (Phyt 1,3-HEU) with a 2D inverse hexagonal phase (HII), and 1-(2-hydroxyethyl)-1-phytanyl urea (Phyt 1,1-HEU) and 1-(2-hydroxyethyl)-3-hexahydrofarnesyl urea (Hfarn 1,3-HEU) with a 3D bicontinuous cubic phase (QII). Phyt 1,1-HEU exhibited rich mesomorphism (QII1, QII2, Lalpha, LU, and HII), as did one other surfactant, oleyl 1,3-HEU (QII1, QII2, Lalpha, LU, and HII), in the study group. LU is an unusual phase which is mobile and isotropic but possesses shear birefringence, and has been very tentatively assigned as an inverse sponge phase. Three other surfactants exhibited a single lyotropic liquid crystalline phase, either Lalpha or HII, at temperatures >50 degrees C. The 10 new surfactants are compared with other recently reported nonionic urea surfactants. Structure-property correlations are examined for

  14. Research on the Long-chain Alkyl Compound Effect on the Conductivity of Polyaniline%长链烷基化合物对聚苯胺电导率影响的研究

    Institute of Scientific and Technical Information of China (English)

    秦序

    2016-01-01

    Mixing polyanline ,Dodecylbenzenesulfonate (referred DBSA) form ion-doped polyaniline poly‐aniline (referred PADB) .In emulsion polymerization resulting product PADB because it contains an exces‐sive amount of DBSA .Before and after cleaning ,we found (pole /di-pole) maximum absorption wave‐length shift is not the same .Acetoneλmax PADB were around 775 and 878nm .Excess of the long -chain alkyl compound is disadvantageous for PADB stretch ,thereby reducing the degree of conductivity ,when the amount of PSS (Polystyrene sulfonate) is less than 10% ,we find (pole /di -pole) transfer of the maximum absorption wavelength red shift ,blue shift when the amount was higher than 10% PSS .%十二烷基苯磺酸(简称DBSA)掺杂聚苯胺形成离子性聚苯胺(简称PADB)。以乳化聚合所得的产物PADB因含有过量的 DBSA 。在清洗前后,发现(极子/双极子)转移的最大吸收波长并不一样。丙酮清洗 PADB前后的λmax 分别为775 nm及878 nm 。过量的长链烷基化合物对 PADB 的伸展是不利的,因而降低电导率数,当PSS(聚苯乙烯磺酸)的量低于10%,发现(极子/双极子)转移的最大吸收波长为红移,当PSS的量高于10%时则为蓝移。

  15. Synthesis and properties evaluation of sulfobetaine surfactant with double hydroxyl

    Science.gov (United States)

    Zhou, Ming; Luo, Gang; Zhang, Ze; Li, Sisi; Wang, Chengwen

    2017-09-01

    A series of sulfobetaine surfactants {N-[(3-alkoxy-2-hydroxyl)propoxy] ethyl-N,N-dimethyl-N-(2-hydroxyl)propyl sulfonate} ammonium chloride were synthesized with raw materials containing linear saturated alcohol, N,N-dimethylethanolamine, sodium 3-chloro-2-hydroxyl propane sulfonic acid and epichlorohydrin. The molecule structures of sulfobetaine surfactants were characterized by FTIR, 1HNMR and elemental analysis. Surface tension measurements can provide us information about the surface tension at the CMC (γCMC), pC20, Γmax and Amin. The pC20 values of sulfobetaine surfactants increase with the hydrophobic chain length increasing. Amin values of the surfactants decrease with increasing hydrophobic chain length from 10 to 14. The critical micelle concentration (CMC) and surface tension (γCMC) values of the sulfobetaine surfactants decrease with increasing hydrophobic chain length from 10 to 16. The lipophilicity of surfactant was enhanced with the increase of the carbon chain, however, the ability of anti-hard water was weakened. The minimum oil/water interfacial tension of four kinds of sulfobetaine surfactants is 10-2-10-3 mN/m magnitude, which indicates that the synthesized bis-hydroxy sulfobetaine surfactants have a great ability to reduce interfacial tension in the surfactant flooding system. The surface tension (γCMC) values of synthesized surfactants were lower compared with conventional anionic surfactant sodium dodecyl sulfonate.

  16. Modification of the activity of an alpha-amylase from Bacillus licheniformis by several surfactants

    OpenAIRE

    2006-01-01

    The influence of different commercial surfactants on the enzymatic activity of a commercial alpha-amylase from Bacillus licheniformis (Termamyl 300 L) has been studied. As non-ionic surfactants, alkyl polyglycosides (Glucopon® 215, Glucopon® 600 and Glucopon® 650) were studied, as were fatty alcohol ethoxylates (Findet 1214N/23 and Findet 10/15), and nonyl phenol ethoxylate (Findet 9Q/21.5NF). Also, an anionic surfactant, linear alkyl benzene sulfonate (LAS) was assayed. In general, none of t...

  17. Electrical conductivity study on micelle formation of long-chain imidazolium ionic liquids in aqueous solution.

    Science.gov (United States)

    Inoue, Tohru; Ebina, Hayato; Dong, Bin; Zheng, Liqiang

    2007-10-01

    Electrical conductivity was measured for aqueous solutions of long-chain imidazolium ionic liquids (IL), 1-alkyl-3-methylimidazolium bromides with C(12)-C(16) alkyl chains. The break points appeared in specific conductivity (kappa) vs concentration (c) plot indicates that the molecular aggregates, i.e., micelles, are formed in aqueous solutions of these IL species. The critical micelle concentration (cmc) determined from the kappa vs c plot is somewhat lower than those for typical cationic surfactants, alkyltrimethylammonium bromides with the same hydrocarbon chain length. The electrical conductivity data were analyzed according to the mixed electrolyte model of micellar solution, and the aggregation number, n, and the degree of counter ion binding, beta, were estimated. The n values of the present ILs are somewhat smaller than those reported for alkyltrimethylammonium bromides, which may be attributed to bulkiness of the cationic head group of the IL species. The thermodynamic parameters for micelle formation of the present ILs were estimated using the values of cmc and beta as a function of temperature. The contribution of entropy term to the micelle formation is superior to that of enthalpy term below about 30 degrees C, and it becomes opposite at higher temperature. This coincides with the picture drawn for the micelle formation of conventional ionic surfactants.

  18. Safety Assessment of Alkyl PEG Sulfosuccinates as Used in Cosmetics.

    Science.gov (United States)

    Johnson, Wilbur; Heldreth, Bart; Bergfeld, Wilma F; Belsito, Donald V; Hill, Ronald A; Klaassen, Curtis D; Liebler, Daniel C; Marks, James G; Shank, Ronald C; Slaga, Thomas J; Snyder, Paul W; Andersen, F Alan

    2015-09-01

    The Cosmetic Ingredient Review (CIR) Expert Panel (Panel) reviewed the safety of alkyl polyethylene glycol (PEG) sulfosuccinates, which function in cosmetics mostly as surfactants/cleansing agents. Although these ingredients may cause ocular and skin irritation, dermal penetration is unlikely because of the substantial polarity and molecular size of these ingredients. The Panel considered the negative oral carcinogenicity and reproductive and developmental toxicity data on chemically related laureths (PEG lauryl ethers) and negative repeated dose toxicity and skin sensitization data on disodium laureth sulfosuccinate supported the safety of these alkyl PEG sulfosuccinates in cosmetic products, but. The CIR Expert Panel concluded that the alkyl PEG sulfosuccinates are safe in the present practices of use and concentration when formulated to be nonirritating.

  19. Analysis of special surfactants by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry.

    Science.gov (United States)

    Wulf, Volker; Wienand, Nils; Wirtz, Michaela; Kling, Hans-Willi; Gäb, Siegmar; Schmitz, Oliver J

    2010-01-29

    Multidimensional gas-chromatographic analyses of olesochemically based nonionic, anionic and several cationic surfactants in industrial cleaners are demonstrated. Comprehensive two-dimensional gas chromatography coupled with time-of-flight mass spectrometry allows the simultaneous determination of fatty alcohols, fatty alcohol sulphates and alkyl polyglucosides. In addition, the determination of fatty alcohol ethoxylates up to C(10)EO(8) (highest degree of ethoxylation) and C(18)EO(5) (longest C-chain at an ethoxylation degree of five) and the analysis of fatty alcohol alkoxylates that contain ethoxy (EO) and propoxy (PO) groups could be realized. Because of decomposition in the injector and a weak EI-fragmentation, cationic surfactants such as alkyl benzyl dimethyl ammonium chloride could also be identified by their characteristic fragments. Thermogravimetric analyses confirmed that the temperature in a normal GC injector is not high enough to cause thermal decomposition of esterquats. However, we could demonstrate that a modified silylation procedure forms decomposition products of esterquats in the GC injector which are detectable by GCxGC-(TOF)MS and allows the identification of such GC-atypical analytes.

  20. EFFECTIVENESS OF WASTE STABILIZATION PONDS IN REMOVAL OF LINEAR ALKYL BENZENE SALFONATE (LAS)

    OpenAIRE

    2013-01-01

    Detergents contain synthetic or organic surface active agents called surfactants, which are derived from petroleum product precursors. They have the common property of lowering the surface tensions of water thus allowing dirt or grease adhered to various articles to be washed off. Linear alkyl benzene sulfonate (LAS) is a most commonly used anionic surfactant. Discharge of raw or treated wastewater containing this chemical substance into the environment causes major public health and envirome...

  1. Estudo microcalorimétrico da interação de tensoativos n-alquil-sulfato de sódio com tripsina a 298 k Microcalorimetric study of sodium N-alkyl sulfate interactions with trypsin at 298 K

    Directory of Open Access Journals (Sweden)

    Eloi A. Silva Filho

    1997-04-01

    Full Text Available Systematic study of the interactions of ionic surfactants with protein trypsin in buffer solution pH 3.5, 7.0 and 9.0, ionic strength 10 mM at 298 K was done using the microcalorimetric technique. In this study, anionic surfactant solutions of the sodium n-alkyl sulfates series (C8, C10, C12 and C14 were used. The enthalpy of interaction (ΔintHº shows that the interaction of the surfactants C8, C10, C12 and C14 with trypsin in the solution pH 3.5 is an endothermic process with the value of ΔintHº decreasing linearly with increasing carbon chain length, which is attributed to the unfolding of the polypeptide chain. In the solution pH 7.0, we observed the same trend except for C14. In the solution pH 9.0, from C10 the enthapy of interaction didn't change with the increasing of the carbon chain length due to unfolding of the polypeptide. We concluded that when trypsin is folded, the enthalpy of interaction shows a linear relationship with the surfactant's hydrophobicity, in agreement with Traube's rule.

  2. Biomimicry of surfactant protein C.

    Science.gov (United States)

    Brown, Nathan J; Johansson, Jan; Barron, Annelise E

    2008-10-01

    considerations but makes use of a non-natural, poly-N-substituted glycine or "peptoid" scaffold to circumvent the difficulties associated with SP-C. By incorporating unique biomimetic side chains in a non-natural backbone, the peptoid mimic captures both SP-C's hydrophobic patterning and its helical secondary structure. Despite the differences in structure, both SP-C33 and the SP-C peptoid mimic capture many requisite features of SP-C. In a surfactant environment, these analogues also replicate many of the key surface activities necessary for a functional biomimetic surfactant therapy while overcoming the difficulties associated with the natural protein. With improved stability, greater production potential, and elimination of possible pathogenic contamination, these biomimetic surfactant formulations offer not only the potential to improve the treatment of respiratory distress syndrome but also the opportunity to treat other respiratory-related disorders.

  3. Gemini surfactants from natural amino acids.

    Science.gov (United States)

    Pérez, Lourdes; Pinazo, Aurora; Pons, Ramon; Infante, Mrosa

    2014-03-01

    In this review, we report the most important contributions in the structure, synthesis, physicochemical (surface adsorption, aggregation and phase behaviour) and biological properties (toxicity, antimicrobial activity and biodegradation) of Gemini natural amino acid-based surfactants, and some potential applications, with an emphasis on the use of these surfactants as non-viral delivery system agents. Gemini surfactants derived from basic (Arg, Lys), neutral (Ser, Ala, Sar), acid (Asp) and sulphur containing amino acids (Cys) as polar head groups, and Geminis with amino acids/peptides in the spacer chain are reviewed.

  4. 2-DE using hemi-fluorinated surfactants.

    Science.gov (United States)

    Starita-Geribaldi, Mireille; Thebault, Pascal; Taffin de Givenchy, Elisabeth; Guittard, Frederic; Geribaldi, Serge

    2007-07-01

    The synthesis of hemi-fluorinated zwitterionic surfactants was realized and assessed for 2-DE, a powerful separation method for proteomic analysis. These new fluorinated amidosulfobetaine (FASB-p,m) were compared to their hydrocarbon counterparts amidosulfobetaine (ASB-n) characterized by a hydrophilic polar head, a hydrophobic and lipophilic tail, and an amido group as connector. The tail of these FASB surfactants was in part fluorinated resulting in the modulation of its lipophilicity (or oleophobicity). Their effect on the red blood cell (RBC) membrane showed a specific solubilization depending on the length of the hydrophobic part. A large number of polypeptide spots appeared in the 2-DE patterns by using FASB-p,m. The oleophobic character of these surfactants was confirmed by the fact that Band 3, a highly hydrophobic transmembrane protein, was not solubilized by these fluorinated structures. The corresponding pellet was very rich in Band 3 and could then be solubilized by using a strong detergent such as amidosulfobetaine with an alkyl tail containing 14 carbon atoms (ASB-14). Thus, these hemi-fluorinated surfactants appeared as powerful tools when used at the first step of a two-step solubilization strategy using a hydrocarbon homologous surfactant in the second step.

  5. Surfactant effects on SF6 hydrate formation.

    Science.gov (United States)

    Lee, Bo Ram; Lee, Ju Dong; Lee, Hyun Ju; Ryu, Young Bok; Lee, Man Sig; Kim, Young Seok; Englezos, Peter; Kim, Myung Hyun; Kim, Yang Do

    2009-03-01

    Sulfur hexafluoride (SF(6)) has been widely used in a variety of industrial processes, but it is one of the most potent greenhouse gases. For this reason, it is necessary to separate or collect it from waste gas streams. One separation method is through hydrate crystal formation. In this study, SF(6) hydrate was formed in aqueous surfactant solutions of 0.00, 0.01, 0.05, 0.15 and 0.20 wt% to investigate the effects of surfactants on the hydrate formation rates. Three surfactants, Tween 20 (Tween), sodium dodecyl sulfate (SDS) and linear alkyl benzene sulfonate (LABS), were tested in a semi-batch stirred vessel at the constant temperature and pressures of 276.2 K and 0.78 MPa, respectively. All surfactants showed kinetic promoter behavior for SF(6) hydrate formation. It was also found that SF(6) hydrate formation proceeded in two stages with the second stage being the most rapid. In situ Raman spectroscopy analysis revealed that the increased gas consumption rate with the addition of surfactant was possibly due to the increased gas filling rate in the hydrate cavity.

  6. Biodegradation of fluorinated alkyl substances.

    Science.gov (United States)

    Frömel, Tobias; Knepper, Thomas P

    2010-01-01

    The incorporation of fluorine into organic molecules entails both positive and adverse effects. Although fluorine imparts positive and unique properties such as water-and oil-repellency and chemical stability, adverse effects often pervade members of this compound class. A striking property of long perfluoroalkyl chains is their very pronounced environmental persistence. The present review is the first one designed to summarize recent accomplishments in the field of biodegradation of fluorine-containing surfactants, their metabolites, and structural analogs. The pronounced scientific and public interest in these chemicals has given impetus to undertake numerous degradation studies to assess the sources and origins of different fluorinated analog chemical known to exist in the environment. It was shown that biodegradation plays an important role in understanding how fluorinated substances reach the environment and, once they do, what their fate is. Today, PFOS and PFOA are ubiquitously detected as environmental contaminants. Their prominence as contaminants is mainly due to their extreme persistence, which is linked to their perfluoroalkyl chain length. It appears that desulfonation of a highly fluorinated surfactants can be achieved if an α-situated H atom, in relation to the sulfonate group, is present, at least under sulfur-limiting conditions. Molecules that are less heavily fluorinated can show very complex metabolic behavior, as is the case for fluorotelomer alcohols. These compounds are degraded via different but simultaneous pathways, which produce different stable metabolites, one of which is the respective perfluoroalkanoate (8:2-FTOH is transformed to PFOA). Preliminary screening tests indicate that fluorinated functional groups, such as the trifluoromethoxy group and the p-(trifluoromethyl)phenoxy group, may be useful implementations in novel, environmentally benign fluorosurfactants. More specifically, trifluoromethoxy groups constitute a substitute

  7. Interfacial assignment of branched-alkyl benzene sulfonates: A molecular simulation

    Directory of Open Access Journals (Sweden)

    Zi-Yu Liu

    2015-11-01

    Full Text Available A molecular dynamics simulation was conducted to analyze orientations of sodium branched-alkyl benzene sulfonates molecules at nonane/water interface, which is helpful to design optimal surfactant structures to achieve ultralow interfacial tension (IFT. Through the two dimensional density profiles, monolayer collapses are found when surfactant concentration continues to increase. Thus the precise scope of monolayer is certain and orientation can be analyzed. Based on the simulated results, we verdict the interfacial assignment of branched-alkyl benzene sulfonates at the oil-water interface, and discuss the effect of hydrophobic tail structure on surfactant assignment. Bigger hydrophobic size can slow the change rate of surfactant occupied area as steric hindrance, and surfactant meta hydrophobic tails have a stronger tendency to stretch to the oil phase below the collapsed concentration. Furthermore, an interfacial model with reference to collapse, increasing steric hindrance and charge repulsive force between interfacial surfactant molecules, responsible for effecting of surfactant concentration and structure has been supposed.

  8. Cationic vesicles based on biocompatible diacyl glycerol-arginine surfactants: physicochemical properties, antimicrobial activity, encapsulation efficiency and drug release.

    Science.gov (United States)

    Tavano, L; Pinazo, A; Abo-Riya, M; Infante, M R; Manresa, M A; Muzzalupo, R; Pérez, L

    2014-08-01

    Physicochemical characteristics of cationic vesicular systems prepared from biocompatible diacyl glycerol-arginine surfactants are investigated. These systems form stable cationic vesicles by themselves and the average diameter of the vesicles decreases as the alkyl chain length of the surfactant increases. The addition of DPPC also modifies the physicochemical properties of these vesicles. Among the drugs these cationic formulations can encapsulate, we have considered Ciprofloxacin and 5-Fluorouracil (5-FU). We show that the percentage of encapsulated drug depends on both the physicochemical properties of the carrier and the type of drug. The capacity of these systems to carry different molecules was evaluated performing in vitro drug release studies. Finally, the antimicrobial activity of empty and Ciprofloxacin-loaded vesicles against Gram-positive and Gram-negative bacteria has been determined. Three bacteria were tested: Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. The in vitro drug release from all formulations was effectively delayed. Empty cationic vesicles showed antimicrobial activity and Ciprofloxacin-loaded vesicles showed similar or higher antimicrobial activity than the free drug solution. These results suggest that our formulations represent a great innovation in the pharmaceutical field, due to their dual pharmacological function: one related to the nature of the vehiculated drug and the other related to the innate antibacterial properties of the surfactant-based carriers.

  9. DETERMINATION OF ALKYLATED & SULFONATED DIPHENYL OXIDE SULFACTANT BY HIGH PERFORMANCE LIQUID CHROMATOGRAPHY

    Science.gov (United States)

    Methods for the determination of the anionic surfactant Dowfax 8390 are described. Dowfax is a complex mixture of various alkylated and sulfonated diphenyl oxides. The primary component of Dowfax is monoalkylated disulfonated diphenyl oxide (MADS). This work uses ion pairing chro...

  10. Flexible polyelectrolyte conformation in the presence of cationic and anionic surfactants

    Science.gov (United States)

    Passos, C. B.; Kuhn, P. S.; Diehl, A.

    2015-11-01

    In this work we have studied the conformation of flexible polyelectrolyte chains in the presence of cationic and anionic surfactant molecules. We developed a simple theoretical model for the formation of the polyelectrolyte-cationic surfactant complexes and mixed micelles formed by cationic and anionic surfactant molecules, in the framework of the Debye-Hückel-Bjerrum-Manning and Flory theories, with the hydrophobic interaction included explicitly as an effective short-ranged attraction between the surfactant hydrocarbon tails. This simple model allows us to calculate the extension of the polyelectrolyte-cationic surfactant complexes as a function of the anionic surfactant concentration, for different types of cationic and anionic surfactant molecules. A discrete conformational transition from a collapsed state to an elongated coil was found, for all surfactant chain lengths we have considered, in agreement with the experimental observations for the unfolding of ​DNA-cationic surfactant complexes.

  11. Effects of alkyl substituents of xanthine on phosphodiesterase isoenzymes.

    Science.gov (United States)

    Miyamoto, K; Sakai, R; Kurita, M; Ohmae, S; Sanae, F; Sawanishi, H; Hasegawa, T; Takagi, K

    1995-03-01

    The structure-activity relationships of a series of alkylxanthine derivatives were investigated. The partition coefficient of alkylxanthines enlarged with an elongation of the alkyl chain at the 1-, 3-, or 7-position of xanthine. There was a mild correlation between the apparent partition coefficient and the tracheal relaxant activity or the inhibitory activity on phosphodiesterase (PDE) IV isoenzyme, while the tracheal relaxant activity closely correlated with the PDE IV inhibitory activity. Regarding substituents at different positions, the alkylation at the 3-position increased the inhibitory activity on every PDE isoenzyme. The alkylation at the 1-position potentiated the inhibitory activity on PDE IV with the alkyl chain length, but decreased the activities on other PDE isoenzymes. The alkylation at the 7-position was characteristic in its decrease in inhibitory activity on PDE III. These results suggested that the potency of the inhibitory activity of xanthine derivatives on PDE isoenzymes is not dependent simply upon their hydrophobicity but upon change in the affinity for the active sites on PDE isoenzymes by the introduction of the alkyl group at particular positions of the xanthine skeleton.

  12. Preparation and evaluation of sulphonamide nonionic surfactants

    Energy Technology Data Exchange (ETDEWEB)

    Ahmed, M. H. M.

    2010-07-01

    Alkyl (octyl, decyl and dodecyl; C{sub 8}, C{sub 1}0 and C{sub 1}2) benzene sulphonyl chloride was used in the preparation of a novel series of nonionic surfactants (IV-VI)a-c, (VII-IX) a-c and (X-XII)a-c. The preparations were completed by reacting each alkyl (C{sub 8}, C{sub 1}0 and C{sub 1}2) benzene sulphonyl chloride with ethanolamine to give (I-III) respectively. The resulting products were reacted separately with ethylene oxide in the presence of different (base KOH, Lewis acid SnCl4 and k10 clay) catalysts to produce different moles of nonionic surfactants (5, 7 and 9) in sequence corresponding to (IV-VI)a-c, (VII-IX) a-c and (X-XII)a-c respectively. The chemical structures of prepared nonionic surfactants were elucidated by IR and 1HNMR spectra. The surface activity, biodegradability and biological activities of the prepared compounds were investigated. The obtained data show that these compounds have good surface and biological activities as well as reasonable biodegradability properties. (Author) 30 refs.

  13. FTIR analysis of the metabolomic stress response induced by N-alkyltropinium bromide surfactants in the yeasts Saccharomyces cerevisiae and Candida albicans.

    Science.gov (United States)

    Corte, Laura; Tiecco, Matteo; Roscini, Luca; Germani, Raimondo; Cardinali, Gianluigi

    2014-04-01

    The activity of surfactants against fungal cells has been studied less than against bacteria, although the medical and industrial importance of the former is of paramount importance. In this paper the surfactant biocidal effect was measured in the yeasts Saccharomyces cerevisiae and Candida albicans with a previously described FTIR bioassay which estimates the stress level as function of the FTIR spectra variation of the cells upon exposition to the chemicals. N-tetradecyltropinium bromide was chosen as stressing agent on the basis of previous preliminary study demonstrating its ability to kill prokaryotic and especially eukaryotic cells at concentration around or over the critical micellar concentration (c.m.c.). Here we show that this surfactant is able to inactivate S. cerevisiae cells at 0.4mM and C. albicans cells at 0.6mM after 1h exposition. FTIR analysis revealed that the surfactant induced metabolomics reactions of S. cerevisiae cells in the regions of amides (W2) and fatty acids (W1). In the same way C. albicans cells showed the maximum stress response in amides (W2) and mixed (W3) regions. Variations of the hydrophobic tail of this surfactant produced a reduced level of cell stress with both the 12C and 16C variants; although these two compounds were more effective in inducing cell mortality in S. cerevisiae but not in C. albicans. In conclusion, this paper has shown that, for this surfactant, the n-alkyl chain must vary between 12C and 16C and that the hydrophilic head size is not as critical as the tail length.

  14. Alkyl resorcinols in grains from plants from the family Gramineae

    Directory of Open Access Journals (Sweden)

    Grzegorz Kubus

    2014-02-01

    Full Text Available 5-n-alkylresorcinols were found in 22 of the 27 studied species of grasses. In Agropyron caninum and Bromus macrostachys only the content of alkyl resorcinols was determined, in Agropyron repens, Bromus mollis and Elymus arenarius the composition of alkyl resorcinol homologues was also established. When calculated per gram of dry mass of air-dried grains, the content of alkyl resorcinols was found to be: in the genus Agropyron - approximately 715 µg, in the genus Bromus approximately 60 µg and in Elymus arenarius, 272 µg. The homologues of alkyl resorcinods in the studied genera of grasses differ from the homologues found in wheat or rye by their greater content of long-chain fractions.

  15. Carbonyl Alkyl Nitrates as Trace Constituents in Urban Air

    Science.gov (United States)

    Woidich, S.; Gruenert, A.; Ballschmiter, K.

    2003-04-01

    Organic nitrates, esters of nitric acid, significantly contribute to the entire pool of odd nitrogen (NOY) in the atmosphere. Organic nitrates are formed in NO rich air by degradation of alkanes and alkenes initiated by OH and NO3 radicals during daytime and nighttime, respectively. Bifunctional organonitrates like the alkyl dinitrates and hydroxy alkyl nitrates are formed primarily from alkenes. The two main sources for Alkenes are traffic emissions and naturally occurring terpenes. So far a broad spectrum of alkyl dinitrates and hydroxy alkyl nitrates including six different isoprene nitrates has been identified in urban and marine air (1-3). We report here for the first time about the group of C4 C7 carbonyl alkyl nitrates as trace constituents in urban air collected on the campus of the University of Ulm Germany, and in the downtown area of Salt Lake City, Utah. Air sampling was done by high volume sampling (flow rate 25 m3/h) using a layer of 100 g silica gel (particle diameter 0.2 - 0.5 mm) as adsorbent. The organic nitrates were eluted from the silica gel by pentane/acetone (4:1, w/w) and the extract was concentrated to a volume of 500 µL for a group separation using normal phase HPLC. Final analysis was performed by high resolution capillary gas chromatography with electron capture detection as well as by mass selective detection in the (CH4)NCI mode using NO2- = m/e 46 as the indicator mass. The carbonyl alkyl nitrates were identified by self synthesized reference standards . So far we have identified eight non-branched a-carbonyl alkyl nitrates (vicinal carbonyl alkyl nitrates), two b-carbonyl alkyl nitrates and one g-carbonyl alkyl nitrate with carbon chains ranging from C4 to C7. The mixing ratios are between 0.05 and 0.30 ppt(v) for daytime samples and are two to three times higher for samples taken at night. (1) M. Schneider, O. Luxenhofer, Angela Deißler, K. Ballschmiter: 2C1-C15 Alkyl Nitrates, Benzyl Nitrate, and Bifunctional Nitrates

  16. Influence of chain length and double bond on the aqueous behavior of choline carboxylate soaps.

    Science.gov (United States)

    Rengstl, Doris; Diat, Olivier; Klein, Regina; Kunz, Werner

    2013-02-26

    In preceding studies, we demonstrated that choline carboxylates ChC(m) with alkyl chain lengths of m = 12 - 18 are highly water-soluble (for m = 12, soluble up to 93 wt % soap and 0 °C). In addition, choline soaps are featured by an extraordinary lyotropic phase behavior. With decreasing water concentration, the following phases were found: micellar phase (L(1)), discontinuous cubic phase (I(1)' and I(1)"), hexagonal phase (H(1)), bicontinuous cubic phase (V(1)), and lamellar phase (L(α)). The present work is also focused on the lyotropic phase behavior of choline soaps but with shorter alkyl chains or different alkyl chain properties. We have investigated the aqueous phase behavior of choline soaps with C(8) and C(10) chain-lengths (choline octanoate and choline decanoate) and with a C(18) chain-length with a cis-double bond (choline oleate). We found that choline decanoate follows the lyotropic phase behavior of the longer-chain homologues mentioned above. Choline octanoate in water shows no discontinuous cubic phases, but an extended, isotropic micellar solution phase. In addition, choline octanoate is at the limit between a surfactant and a hydrotrope. The double bond in choline oleate leads also to a better solubility in water and a decrease of the solubilization temperature. It also influences the Gaussian curvature of the aggregates which results in a loss of discontinuous cubic phases in the binary phase diagram. The different lyotropic mesophases were identified by the penetration scan technique with polarizing light microscope and visual observations. To clarify the structural behavior small (SAXS) and wide (WAXS) angle X-ray scattering were performed. To further characterize the extended, isotropic micellar solution phase in the binary phase diagram of choline octanoate viscosity and conductivity measurements were also carried out.

  17. Theory of phase equilibria for model mixtures of n-alkanes, perfluoroalkanes and perfluoroalkylalkane diblock surfactants

    Science.gov (United States)

    Dos Ramos, María Carolina; Blas, Felipe J.

    2007-05-01

    An extension of the SAFT-VR equation of state, the so-called hetero-SAFT approach [Y. Peng, H. Zhao, and C. McCabe, Molec. Phys. 104, 571 (2006)], is used to examine the phase equilibria exhibited by a number of model binary mixtures of n-alkanes, perfluoroalkanes and perfluoroalkylalkane diblock surfactants. Despite the increasing recent interest in semifluorinated alkanes (or perfluoroalkylalkane diblock molecules), the phase behaviour of mixtures involving these molecules with n-alkanes or perfluoroalkanes is practically unknown from the experimental point of view. In this work, we use simple molecular models for n-alkanes, perfluoroalkanes and perfluoroalkylalkane diblock molecules to predict, from a molecular perspective, the phase behaviour of selected model mixtures of perfluoroalkylalkanes with n-alkanes and perfluoroalkanes. In particular, we focus our interest on the understanding of the microscopic conditions that control the liquid-liquid separation and the stabilization of these mixtures. n-Alkanes and perfluoroalkanes are modelled as tangentially bonded monomer segments with molecular parameters taken from the literature. The perfluoroalkylalkane diblock molecules are modelled as heterosegmented diblock chains, with parameters for the alkyl and perfluoroalkyl segments developed in earlier work. This simple approach, which was proposed in previous work [P. Morgado, H. Zhao, F. J. Blas, C. McCabe, L. P. N. Rebelo, and E. J. M. Filipe, J. Phys. Chem. B, 111, 2856], is now extended to describe model n-alkane (or perfluoroalkane) + perfluroalkylalkane binary mixtures. We have obtained the phase behaviour of different mixtures and studied the effect of the molecular weight of n-alkanes and perfluoroalkanes on the type of phase behaviour observed in these mixtures. We have also analysed the effect of the number of alkyl and perfluoroalkyl chemical groups in the surfactant molecule on the phase behaviour. In addition to the usual vapour-liquid phase

  18. Synthesis and antiviral activity of some C2-, C4-, and C6-substituted pyrazolo[3,4-D]pyrimidine acyclonucleosides with the alkylating chains of ACV, HBG, and ISO-DHPG.

    Science.gov (United States)

    Moukha-Chafiq, Omar; Taha, Mohamed Labd; Lazrek, Hassan Bihi; Vasseur, Jean-Jacques; Clercq, Erik De

    2006-01-01

    A useful route to obtain trisubstituted pyrazolo[3,4-d]pyrimidines 14-17 is described. Those later were coupled with the alkylating agents 18-20 as in ACV, HBG, and iso-DHPG to give, after deprotection, the desired acylonucleosides 33-44. Almost all of the new compounds were evaluated for their inhibitory effects against the replication of various DNA viruses in culture.

  19. Enzymatic Synthesis of Palm Alkyl Ester Using Dialkyl Carbonate as an Alkyl Donors

    Directory of Open Access Journals (Sweden)

    Roila Awang

    2010-01-01

    Full Text Available Problem statement: Though efficient in terms of reaction yield and time, the chemical approach to synthesizing alkyl ester has drawback such as difficulties in the recovery of glycerol and the need for removal of salt residue. On the other hand, biocatalyst allow for synthesis of specific alkyl esters and easy recovery of glycerol. However, the solvent-free alcoholysis, does not give high conversion. The same problem was also found when ethyl or methyl acetate was used as acyl acceptors. Approach: Lipase catalyzed transesterification of oil and dialkyl carbonate was predicted to give higher conversion in solvent free reaction system. Results: Alkyl esters were synthesized enzymatically to overcome the problems associated with chemical processes. In this study, dialkyl carbonates were used as an alkyl donor for the production of alkyl ester. Nine commercial lipases were tested for their suitability for the reaction system. Among the lipase tested, Novozym 435 was chosen for optimization study because of their higher activity. In a solvent-free reaction system, the ester formation using dialkyl carbonate was 6 times higher than using ethanol and methanol. The effect of various reaction parameters such as temperature, amount of enzyme, organic solvent and structure of substrates were studied to determine optimal condition. The optimal conditions of ester formation were reaction temperature at 60°C, reaction time at 8 h, enzyme amount of 10% (w/w of oil and 0.2% wt added water. Conclusion: Solvent-free lipase catalyzed transesterification of palm kernel oil and dialkyl carbonates gave higher conversion of ester compared to the reaction using short chain alcohol as an alkyl donors.

  20. Thermally cleavable surfactants

    Science.gov (United States)

    McElhanon, James R.; Simmons, Blake A.; Zifer, Thomas; Jamison, Gregory M.; Loy, Douglas A.; Rahimian, Kamyar; Long, Timothy M.; Wheeler, David R.; Staiger, Chad L.

    2006-04-04

    Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60.degree. C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments and the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.

  1. Thermally cleavable surfactants

    Energy Technology Data Exchange (ETDEWEB)

    McElhanon, James R. (Manteca, CA); Simmons, Blake A. (San Francisco, CA); Zifer, Thomas (Manteca, CA); Jamison, Gregory M. (Albuquerque, NM); Loy, Douglas A. (Albuquerque, NM); Rahimian, Kamyar (Albuquerque, NM); Long, Timothy M. (Urbana, IL); Wheeler, David R. (Albuquerque, NM); Staiger, Chad L. (Albuquerque, NM)

    2009-09-29

    Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60.degree. C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments or the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.

  2. Thermally cleavable surfactants

    Energy Technology Data Exchange (ETDEWEB)

    McElhanon, James R. (Manteca, CA); Simmons, Blake A. (San Francisco, CA); Zifer, Thomas (Manteca, CA); Jamison, Gregory M. (Albuquerque, NM); Loy, Douglas A. (Albuquerque, NM); Rahimian, Kamyar (Albuquerque, NM); Long, Timothy M. (Urbana, IL); Wheeler, David R. (Albuquerque, NM); Staiger, Chad L. (Albuquerque, NM)

    2009-11-24

    Two new surfactant molecules are reported which contain thermally labile Diels-Alder adducts connecting the polar and non-polar sections of each molecule. The two surfactants possess identical non-polar dodecyl tail segments but exhibit different polar headgroups. The surfactants become soluble in water when anionic salts are formed through the deprotonation of the surfactant headgroups by the addition of potassium hydroxide. When either surfactant is exposed to temperature above about 60.degree. C., the retro Diels-Alder reaction occurs, yielding hydrophilic and hydrophobic fragments or the aqueous solutions of the surfactants subsequently exhibit loss of all surface-active behavior.

  3. Catalytic Alkylation of 2-Methylfuran with Formalin Using Supported Acidic Ionic Liquids

    DEFF Research Database (Denmark)

    Li, Hu; Shunmugavel, Saravanamurugan; Yang, Song;

    2015-01-01

    Biphasic alkylation of 2-methylfuran (2-MF) with formalin was carried out with a series of SBA-15 supported acidic ionic liquid catalysts (acidic SILCs) under mild reaction conditions. Acidic SILC with sulfonic acid groups (SO3H) and long alkyl chains was observed to have higher catalytic activity...

  4. Towards understanding the mechanism of action of antibacterial N-alkyl-3-hydroxypyridinium salts: Biological activities, molecular modeling and QSAR studies.

    Science.gov (United States)

    Dolezal, Rafael; Soukup, Ondrej; Malinak, David; Savedra, Ranylson M L; Marek, Jan; Dolezalova, Marie; Pasdiorova, Marketa; Salajkova, Sarka; Korabecny, Jan; Honegr, Jan; Ramalho, Teodorico C; Kuca, Kamil

    2016-10-01

    In this study, we have carried out a combined experimental and computational investigation to elucidate several bred-in-the-bone ideas standing out in rational design of novel cationic surfactants as antibacterial agents. Five 3-hydroxypyridinium salts differing in the length of N-alkyl side chain have been synthesized, analyzed by high performance liquid chromatography, tested for in vitro activity against a panel of pathogenic bacterial and fungal strains, computationally modeled in water by a SCRF B3LYP/6-311++G(d,p) method, and evaluated by a systematic QSAR analysis. Given the results of this work, the hypothesis suggesting that higher positive charge of the quaternary nitrogen should increase antimicrobial efficacy can be rejected since 3-hydroxyl group does increase the positive charge on the nitrogen but, simultaneously, it significantly derogates the antimicrobial activity by lowering the lipophilicity and by escalating the desolvation energy of the compounds in comparison with non-hydroxylated analogues. Herein, the majority of the prepared 3-hydroxylated substances showed notably lower potency than the parent pyridinium structures, although compound 8 with C12 alkyl chain proved a distinctly better antimicrobial activity in submicromolar range. Focusing on this anomaly, we have made an effort to reveal the reason of the observed activity through a molecular dynamics simulation of the interaction between the bacterial membrane and compound 8 in GROMACS software.

  5. Remediation of nitrobenzene contaminated soil by combining surfactant enhanced soil washing and effluent oxidation with persulfate.

    Directory of Open Access Journals (Sweden)

    Jingchun Yan

    Full Text Available The combination of surfactant enhanced soil washing and degradation of nitrobenzene (NB in effluent with persulfate was investigated to remediate NB contaminated soil. Aqueous solution of sodium dodecylbenzenesulfonate (SDBS, 24.0 mmol L-1 was used at a given mass ratio of solution to soil (20:1 to extract NB contaminated soil (47.3 mg kg-1, resulting in NB desorption removal efficient of 76.8%. The washing effluent was treated in Fe2+/persulfate and Fe2+/H2O2 systems successively. The degradation removal of NB was 97.9%, being much higher than that of SDBS (51.6% with addition of 40.0 mmol L-1 Fe2+ and 40.0 mmol L-1 persulfate after 15 min reaction. The preferential degradation was related to the lone pair electron of generated SO4•-, which preferably removes electrons from aromatic parts of NB over long alkyl chains of SDBS through hydrogen abstraction reactions. No preferential degradation was observed in •OH based oxidation because of its hydrogen abstraction or addition mechanism. The sustained SDBS could be reused for washing the contaminated soil. The combination of the effective surfactant-enhanced washing and the preferential degradation of NB with Fe2+/persulfate provide a useful option to remediate NB contaminated soil.

  6. Surfactant-assisted liquefaction of particulate carbonaceous substances

    Science.gov (United States)

    Hsu, G. C. (Inventor)

    1978-01-01

    A slurry of carbonaceous particles such as coal containing an oil soluble polar substituted oleophilic surfactant, suitably an amine substituted long chain hydrocarbon, is liquefied at high temperature and high hydrogen presence. The pressure of surfactant results in an increase in yield and the conversion product contains a higher proportion of light and heavy oils and less asphaltene than products from other liquefaction processes.

  7. New Y-shaped surfactants from renewable resources.

    Science.gov (United States)

    Ali, Tammar Hussein; Hussen, Rusnah Syahila Duali; Heidelberg, Thorsten

    2014-11-01

    A series of sugar-based surfactants, involving a single hydrophobic chain (C12) and two side-by-side arranged head groups, was prepared form simple glucose precursors. All surfactants were highly water soluble and exhibited exclusively micellar assemblies. This behavior makes them interesting candidates for oil in water emulsifiers. Copyright © 2014 Elsevier B.V. All rights reserved.

  8. Perfluoroalkyl Epoxides: Synthesis and Conversion into Ionic Surfactants

    Directory of Open Access Journals (Sweden)

    Abdelhamid Ayari

    2014-07-01

    Full Text Available Perfluoroalkylated surfactants having a quaternary ammonium surrounded by three hydroxyl groups as hydrophilic moiety and a perfluoroalkyl chain as tail were obtained by coupling diethanolamine with perfluoroalkylated epoxide followed by quaternisation. The amphiphilic properties of these surfactants were investigated by measuring their surface and interfacial tensions.

  9. New mechanisms for phase separation in polymer-surfactant mixtures

    NARCIS (Netherlands)

    Currie, E.P.K.; Cohen Stuart, M.A.; Borisov, O.V.

    2000-01-01

    The cooperative association of ionic surfactants with polymer chains leads to quite novel features in the phase behaviour of polymer solutions. Using an analytic mean-field model, we analyze phase equilibria in solutions of neutral polymers mixed with ionic surfactants. We predict the possibilities

  10. Method of making alkyl esters

    Science.gov (United States)

    Elliott, Brian

    2010-09-14

    Methods of making alkyl esters are described herein. The methods are capable of using raw, unprocessed, low-cost feedstocks and waste grease. Generally, the method involves converting a glyceride source to a fatty acid composition and esterifying the fatty acid composition to make alkyl esters. In an embodiment, a method of making alkyl esters comprises providing a glyceride source. The method further comprises converting the glyceride source to a fatty acid composition comprising free fatty acids and less than about 1% glyceride by mass. Moreover, the method comprises esterifying the fatty acid composition in the presence of a solid acid catalyst at a temperature ranging firm about 70.degree. C. to about 120.degree. C. to produce alkyl esters, such that at least 85% of the free fatty acids are converted to alkyl esters. The method also incorporates the use of packed bed reactors for glyceride conversion and/or fatty acid esterification to make alkyl esters.

  11. Tunable, antibacterial activity of silicone polyether surfactants.

    Science.gov (United States)

    Khan, Madiha F; Zepeda-Velazquez, Laura; Brook, Michael A

    2015-08-01

    Silicone surfactants are used in a variety of applications, however, limited data is available on the relationship between surfactant structure and biological activity. A series of seven nonionic, silicone polyether surfactants with known structures was tested for in vitro antibacterial activity against Escherichia coli BL21. The compounds varied in their hydrophobic head, comprised of branched silicone structures with 3-10 siloxane linkages and, in two cases, phenyl substitution, and hydrophilic tail of 8-44 poly(ethylene glycol) units. The surfactants were tested at three concentrations: below, at, and above their Critical Micelle Concentrations (CMC) against 5 concentrations of E. coli BL21 in a three-step assay comprised of a 14-24h turbidometric screen, a live-dead stain and viable colony counts. The bacterial concentration had little effect on antibacterial activity. For most of the surfactants, antibacterial activity was higher at concentrations above the CMC. Surfactants with smaller silicone head groups had as much as 4 times the bioactivity of surfactants with larger groups, with the smallest hydrophobe exhibiting potency equivalent to sodium dodecyl sulfate (SDS). Smaller PEG chains were similarly associated with higher potency. These data link lower micelle stability and enhanced permeability of smaller silicone head groups to antibacterial activity. The results demonstrate that simple manipulation of nonionic silicone polyether structure leads to significant changes in antibacterial activity.

  12. Transesterified tyrosol and hydroxytyrosol alkyl esters from cuphea oil – antioxidant behavior in Liposomes

    Science.gov (United States)

    Tyrosol and hydroxytyrosol are the antioxidant molecules abundantly found in olive oil. Transesterification of tyrosol and hydroxytyrosol with cuphea oil results in medium chain alkyl esters with antioxidant properties. Membrane partitioning, antioxidant capacity, and membrane location of these nove...

  13. Effect of alkyl substitutions on self-assembly

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    The self-assemblies of 4-hexadecyloxybenzoic acid and 3,4,5-trihexadecyloxybenzoic acid have been studied by using scanning tunneling microscopy (STM). The well-ordered assemblies with different arrangement have been investigated. The structural change is attributed to the different number of substituted alkyl chains on periphery.

  14. Effects of alkyl substitutions of xanthine skeleton on bronchodilation.

    Science.gov (United States)

    Sakai, R; Konno, K; Yamamoto, Y; Sanae, F; Takagi, K; Hasegawa, T; Iwasaki, N; Kakiuchi, M; Kato, H; Miyamoto, K

    1992-10-30

    Structure-activity relationships in a series of 1,3,7-trialkyl-xanthine were studied with guinea pigs. Relaxant actions in the tracheal muscle were increased with alkyl chain length at the 1- and 3-positions of the xanthine skeleton, but decreased by alkylation at the 7-position. Positive chronotropic actions in the right atrium were potentiated with 3-alkyl chain length but tended to decrease with 1-alkylation and diminish by 7-substitution. Consequently, while the 1- and 3-substitutions were equally important for the tracheal smooth muscle relaxation, the substitution at the 1-position was more important than the 3-substitution for bronchoselectivity. The 7-alkylation may be significant to cancel heart stimulation. There were good correlations between the smooth muscle relaxant action and the cyclic AMP-PDE inhibitory activity in 3-substituents and the affinity for adenosine (A1) receptors in 1-, 3-, and 7-substituents. This suggests that not only the cyclic AMP-PDE inhibitory activity but also the adenosine antagonistic activity is important in the bronchodilatory effects of alkylxanthines. Among these xanthine derivatives, 1-butyl-3-propylxanthine and its 7-methylated derivative showed high bronchoselectivity in the in vitro and in vivo experiments compared to theophylline and enprofylline and may be new candidates for bronchodilator.

  15. Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones.

    Science.gov (United States)

    Shimada, Hideaki; Tanigawa, Takahiro; Matayoshi, Kazunori; Katakura, Kazufumi; Babazono, Ken; Takayama, Hiroyuki; Murahashi, Tsuyoshi; Akita, Hiroyuki; Higuchi, Toshiyuki; Eto, Masashi; Imamura, Yorishige

    2014-06-01

    The present study is to elucidate the comparative inhibition of tetrameric carbonyl reductase (TCBR) activity by alkyl 4-pyridyl ketones, and to characterize its substrate-binding domain. The inhibitory effects of alkyl 4-pyridyl ketones on the stereoselective reduction of 4-benzoylpyridine (4-BP) catalyzed by TCBR were examined in the cytosolic fraction of pig heart. Of alkyl 4-pyridyl ketones, 4-hexanoylpyridine, which has a straight-chain alkyl group of five carbon atoms, inhibited most potently TCBR activity and was a competitive inhibitor. Furthermore, cyclohexyl pentyl ketone, which is substituted by cyclohexyl group instead of phenyl group of hexanophenone, had much lower ability to be reduced than hexanophenone. These results suggest that in addition to a hydrophobic cleft corresponding to a straight-chain alkyl group of five carbon atoms, a hydrophobic pocket with affinity for an aromatic group is located in the substrate-binding domain of TCBR.

  16. Solid-phase extraction-gas chromatography and solid-phase extraction-gas chromatography-mass spectrometry determination of corrosion inhibiting long-chain primary alkyl amines in chemical treatment of boiler water in water-steam systems of power plants.

    Science.gov (United States)

    Kusch, Peter; Knupp, Gerd; Hergarten, Marcus; Kozupa, Marian; Majchrzak, Maria

    2006-04-28

    Gas chromatography with simultaneous flame-ionization detection (FID) and a nitrogen-phosphorus detection (NPD) as well as gas chromatography-mass spectrometry (GC/MS) has been used to characterize long-chain primary alkyl amines after derivatization with trifluoroacetic anhydride (TFAA). Electron impact ionization- (EI) and negative chemical ionization (NCI) mass spectra of trifluoroacetylated derivatives of the identified tert-octadecylamines are presented for the first time. The corrosion inhibiting alkyl amines were applied in a water-steam circuit of energy systems in the power industry. Solid-phase extraction (SPE) with octadecyl bonded silica (C18) sorbents followed by gas chromatography were used for quantification of the investigated tert-octadecylamines in boiler water, superheated steam and condensate samples from the power plant. The estimated values were: 89 microg l(-1)(n = 5, RSD = 7.8%), 45 microg l(-1) (n = 5, RSD = 5.4%) and 37 microg l(-1)(n = 5, RSD = 2.3%), respectively.

  17. Biodegradability and toxicity of sulphonate-based surfactants in aerobic and anaerobic aquatic environments.

    Science.gov (United States)

    García, M T; Campos, E; Marsal, A; Ribosa, I

    2009-02-01

    Four types of commonly used sulphonate-based surfactants (alkane sulphonates, alpha-olefin sulphonates, sulphosuccinates and methyl ester sulphonates) were tested for their aerobic and anaerobic biodegradability as well as for their toxicity to Daphnia magna and Photobacterium phosphoreum to assess the effect of the surfactant structure on those properties. Aerobic biodegradation was evaluated by means of the CO2 headspace test and anaerobic biodegradation was assessed by a method based on the ECETOC test. All the surfactants tested were readily biodegraded under aerobic conditions. No clear effect of the surfactant structures on the toxicity to the aquatic organisms tested was found. The most significant differences in the surfactants studied were observed in their behaviour under anaerobic conditions. Alkane sulphonates, alpha-olefin sulphonates and methyl ester sulphonates were not mineralized in lab anaerobic digesters despite the fact that the last one showed a certain degree of primary degradation. Nevertheless, these surfactants did not significantly inhibit methanogenic activity at concentrations up to 15 g surfactant/kg dry sludge, a concentration that is much higher than the expected concentrations of these surfactants in real anaerobic digesters. Sulphosuccinates showed a high level of primary biodegradation in anaerobic conditions. However, linear alkyl sulphosuccinates were completely mineralized whereas branched alkyl sulphosuccinates achieved percentages of ultimate biodegradation < or =50%.

  18. Enhanced solubilization of curcumin in mixed surfactant vesicles.

    Science.gov (United States)

    Kumar, Arun; Kaur, Gurpreet; Kansal, S K; Chaudhary, Ganga Ram; Mehta, S K

    2016-05-15

    Self-assemblies of equimolar double and single chain mixed ionic surfactants, with increasing numbers of carbon atoms of double chain surfactant, were analyzed on the basis of fluorescence and conductivity results. Attempts were also made to enhance the solubilization of curcumin in aqueous equimolar mixed surfactant systems. Mixed surfactant assembly was successful in retarding the degradation of curcumin in alkaline media (only 25-28 40% degraded in 10h at pH 13). Fluorescence spectroscopy and fluorescence quenching methods were employed to predict the binding position and mechanism of curcumin with self-assemblies. Results indicate that the interactions take place according to both dynamic and static quenching mechanisms and curcumin was distributed in a palisade layer of mixed aggregates. Antioxidant activity (using DPPH radical) and biocompatibility (using calf-thymus DNA) of curcumin-loaded mixed surfactant formulations were also evaluated. The prepared systems improved the stability, solubility and antioxidant activity of curcumin and additionally are biocompatible.

  19. Polymer-hybridized liposomes anchored with alkyl grafted poly(asparagine).

    Science.gov (United States)

    Park, Sung-Il; Lee, Eun-Ok; Kim, Jin Woong; Kim, Youn Joon; Han, Sang Hoon; Kim, Jong-Duk

    2011-12-01

    Polymer-hybridized liposomes (PHLs) of saturated lecithin were formed by association of poly(asparagines) grafted with alkyl chains (PAsn-g-Cn). The thermal, physical, and surface properties of the polymer-hybridized liposomes were examined with varying polymer concentration, alkyl chain length (C(8), C(12), C(18), C(22)), and degree of substitution (DS) in the polymer. The inclusion of the polymer raised the membrane fluidity of liposomes. By the incorporation of small amount of polymer, the membrane rigidity of liposomes dropped sharply and then increased close to the original level as the polymer concentrations increased in the cases of PAsn-g-C(18) and PAsn-g-C(22). Also, the membrane rigidity and stability of PHLs increased with alkyl chain length at the same polymer concentration. The surface charge of PHL associated with PAsn-g-C(22) was changed by DS of alkyl chains. The polymer bearing long alkyl chains (C(12), C(18), C(22)) formed PHLs well at low polymer concentration and the number of disk-shaped polymer-lipid mixed micelles increased with polymer concentration. The anchored polymers induced shifts in gel-to-liquid crystal transition temperature (Tc) of the vesicles and Tc varied with polymer concentration, alkyl chain length, and DS of the polymer.

  20. Foaming and foam stability for mixed polymer-surfactant solutions: effects of surfactant type and polymer charge.

    Science.gov (United States)

    Petkova, R; Tcholakova, S; Denkov, N D

    2012-03-20

    Solutions of surfactant-polymer mixtures often exhibit different foaming properties, compared to the solutions of the individual components, due to the strong tendency for formation of polymer-surfactant complexes in the bulk and on the surface of the mixed solutions. A generally shared view in the literature is that electrostatic interactions govern the formation of these complexes, for example between anionic surfactants and cationic polymers. In this study we combine foam tests with model experiments to evaluate and explain the effect of several polymer-surfactant mixtures on the foaminess and foam stability of the respective solutions. Anionic, cationic, and nonionic surfactants (SDS, C(12)TAB, and C(12)EO(23)) were studied to clarify the role of surfactant charge. Highly hydrophilic cationic and nonionic polymers (polyvinylamine and polyvinylformamide, respectivey) were chosen to eliminate the (more trivial) effect of direct hydrophobic interactions between the surfactant tails and the hydrophobic regions on the polymer chains. Our experiments showed clearly that the presence of opposite charges is not a necessary condition for boosting the foaminess and foam stability in the surfactant-polymer mixtures studied. Clear foam boosting (synergistic) effects were observed in the mixtures of cationic surfactant and cationic polymer, cationic surfactant and nonionic polymer, and anionic surfactant and nonionic polymer. The mixtures of anionic surfactant and cationic polymer showed improved foam stability, however, the foaminess was strongly reduced, as compared to the surfactant solutions without polymer. No significant synergistic or antagonistic effects were observed for the mixture of nonionic surfactant (with low critical micelle concentration) and nonionic polymer. The results from the model experiments allowed us to explain the observed trends by the different adsorption dynamics and complex formation pattern in the systems studied.

  1. Quantitative Structure-Activity Relationships in the Lithium and Sodium Affinities of n-Alkyl Fluorides

    Institute of Scientific and Technical Information of China (English)

    2002-01-01

    B3LYP/6-31+g (d, p) method was used to calculate the lithium and sodium affinities of n-alkyl fluoride. These affinities were found to obey the Holmes relationship, i.e. they correlate linearly with the quotient n/(n+1), where n is the number of carbon atoms in the alkyl chain. From the correlation the limiting values of lithium and sodium affinities for very long alkyl chain were predicted to be -153.3 kJ/mol and -108.4 kJ/mol, respectively.

  2. Quantitative Structure—Activity Relationships in the Lithium and Sodium Affinities of n—Alkyl Fluorides

    Institute of Scientific and Technical Information of China (English)

    KeChunZHANG; JianMiaoFAN; 等

    2002-01-01

    B3L YP/6-31+g(d,p)method was used to calculate the lithium and sodium affinities of n-alkyl fluoride. These affinities were found to obey the Holmes relationship, i.e.they correlate linearly with the quotient n/(n+1), where n is the number of carbon atoms in the alkyl chain. From the correlation the limiting values of lithium and sodium affinities for very long alkyl chain were predicted to be-153.3kJ/mol and -108.4kJ/mol,respectively.

  3. A GH57 4-α-glucanotransferase of hyperthermophilic origin with potential for alkyl glycoside production.

    Science.gov (United States)

    Paul, Catherine J; Leemhuis, Hans; Dobruchowska, Justyna M; Grey, Carl; Önnby, Linda; van Leeuwen, Sander S; Dijkhuizen, Lubbert; Karlsson, Eva Nordberg

    2015-09-01

    4-α-Glucanotransferase (GTase) enzymes (EC 2.4.1.25) modulate the size of α-glucans by cleaving and reforming α-1,4 glycosidic bonds in α-glucans, an essential process in starch and glycogen metabolism in plants and microorganisms. The glycoside hydrolase family 57 enzyme (GTase57) studied in the current work catalyzes both disproportionation and cyclization reactions. Amylose was converted into cyclic amylose (with a minimum size of 17 glucose monomers) as well as to a spectrum of maltodextrins, but in contrast to glycoside hydrolase family 13 cyclodextrin glucanotransferases (CGTases), no production of cyclodextrins (C6-C8) was observed. GTase57 also effectively produced alkyl-glycosides with long α-glucan chains from dodecyl-β-D-maltoside and starch, demonstrating the potential of the enzyme to produce novel variants of surfactants. Importantly, the GTase57 has excellent thermostability with a maximal activity at 95 °C and an activity half-life of 150 min at 90 °C which is highly advantageous in this manufacturing process suggesting that enzymes from this relatively uncharacterized family, GH57, can be powerful biocatalysts for the production of large head group glucosides from soluble starch.

  4. LOWER COST METHODS FOR IMPROVED OIL RECOVERY (IOR) VIA SURFACTANT FLOODING

    Energy Technology Data Exchange (ETDEWEB)

    William A. Goddard III; Yongchun Tang; Patrick Shuler; Mario Blanco; Seung Soon Jang; Shiang-Tai Lin; Prabal Maiti; Yongfu Wu; Stefan Iglauer; Xiaohang Zhang

    2004-09-01

    This report provides a summary of the work performed in this 3-year project sponsored by DOE. The overall objective of this project is to identify new, potentially more cost-effective surfactant formulations for improved oil recovery (IOR). The general approach is to use an integrated experimental and computational chemistry effort to improve our understanding of the link between surfactant structure and performance, and from this knowledge, develop improved IOR surfactant formulations. Accomplishments for the project include: (1) completion of a literature review to assemble current and new surfactant IOR ideas, (2) Development of new atomistic-level MD (molecular dynamic) modeling methodologies to calculate IFT (interfacial tension) rigorously from first principles, (3) exploration of less computationally intensive mesoscale methods to estimate IFT, Quantitative Structure Property Relationship (QSPR), and cohesive energy density (CED) calculations, (4) experiments to screen many surfactant structures for desirable low IFT and solid adsorption behavior, and (5) further experimental characterization of the more promising new candidate formulations (based on alkyl polyglycosides (APG) and alkyl propoxy sulfate surfactants). Important findings from this project include: (1) the IFT between two pure substances may be calculated quantitatively from fundamental principles using Molecular Dynamics, the same approach can provide qualitative results for ternary systems containing a surfactant, (2) low concentrations of alkyl polyglycoside surfactants have potential for IOR (Improved Oil Recovery) applications from a technical standpoint (if formulated properly with a cosurfactant, they can create a low IFT at low concentration) and also are viable economically as they are available commercially, and (3) the alkylpropoxy sulfate surfactants have promising IFT performance also, plus these surfactants can have high optimal salinity and so may be attractive for use in higher

  5. Mixing Effect of Polyoxyethylene-Type Nonionic Surfactants on the Liquid Crystalline Structures.

    Science.gov (United States)

    Kunieda; Umizu; Yamaguchi

    1999-10-01

    An effective cross-sectional area per surfactant molecule at hydrophobic interfaces of aggregates, a(S), in hexagonal (H(1)) and lamellar (L(alpha)) liquid crystals was calculated in homogeneous and mixed polyoxyethylene dodecyl ether systems as a function of polyoxyethylene (EO) chain length by means of small-angle X-ray scattering. The a(S) increases with increasing the EO chain length. The a(S) in the mixed surfactant system is considerably smaller than that in the single surfactant system, even if the average EO chain length is the same. The reduction of a(S) is larger than that predicted by ideal mixing of the surfactants. Moreover, if the EO chain lengths of the surfactants are more separated, the a(S) is smaller. The shapes of surfactant self-organizing structures may be governed by the balance of the attractive and the repulsive forces acting at the hydrophobic interfaces of the aggregates. According to this consideration, the mixing effect of surfactants with the different EO chain lengths on the a(S) in the L(alpha) phase was discussed. It is considered that the surfactant molecules are tightly packed in the aggregates since the reduction in repulsion force takes place in the excess EO chain part of the hydrophilic surfactant longer than the short EO chain of the lipophilic one. The lower surface tensions and the better stability of macroemulsions and the large solubilizing capacity of microemulsions result from the mixing effect. Copyright 1999 Academic Press.

  6. Synthesis of organic rectorite with novel Gemini surfactants for copper removal

    Energy Technology Data Exchange (ETDEWEB)

    Han, Guocheng; Han, Yang [State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640 (China); Wang, Xiaoying, E-mail: xyw@scut.edu.cn [State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640 (China); Liu, Shijie, E-mail: sjliu@163.com [State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640 (China); Department of Paper and Bioprocess Engineering, State University of New York, College of Environmental Science and Forestry, 1 Forestry Drive, Syracuse, NY 13210 (United States); Sun, Runcang [State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640 (China); China Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, Beijing 100083 (China)

    2014-10-30

    Graphical abstract: Three Gemini surfactants showed stronger rapid intercalation capacity into rectorite and behaved better on Cu{sup 2+} removal than two single-chain surfactants, which were positive to their increasing amount and chain length. - Highlights: • Modification of rectorite (REC) with several surfactants was performed in 1 h. • The arrangement of Gemini surfactants in REC layers was discussed. • All ORECs displayed better adsorption capacities on Cu{sup 2+} than pure REC. • Gemini-REC behaved better than single-chain surfactant modified REC on Cu{sup 2+} removal. • The adsorption capacity was positive to the amount and chain length of surfactant. - Abstract: Three novel Gemini surfactants were used to prepare organic rectorite (OREC) under microwave irradiation, in comparison with single-chain surfactant ester quaternary ammonium salt (EQAS) and cetyltrimethyl ammonium bromide (CTAB). The structure and morphology of OREC were characterized by XRD, BET, FT-IR, TEM and TGA. The removal of Cu{sup 2+} on OREC from aqueous solution was performed. The results reveal that Gemini surfactants modified REC had larger interlayer distance and higher surface area than single-chain surfactants EQAS and CTAB, and the increasing amount or chain length of Gemini surfactants led to larger layer spacing and higher adsorption capacities. The adsorption behavior of Gemini surfactant modified REC can be better described by Freundlich adsorption isotherm model, with a maximum adsorption capacity of 15.16 mg g{sup −1}. The desorption and regeneration experiments indicate good reuse property of Gemini modified REC adsorbent. Therefore, this study may widen the utilization of Gemini surfactants modified layered silicates.

  7. Heat-regulated foaming in surfactant solutions

    Energy Technology Data Exchange (ETDEWEB)

    Pletnev, M.Y.; Eremina, L.D.; Vlasenko, I.G.

    1984-01-01

    This article examines the mechanism of the foam-inhibiting action resulting from the use of propylene oxide derivatives in solutions both of anionic and of nonionic surfactants. The objective is the creation of a detergent composition with heat-regulated foaming, which would foam well at 30-50/sup 0/ and poorly at 80-90/sup 0/, which is the usual temperature of washing machines. It is demonstrated that foaming can be regulated by the variation of the cloud points of solutions with the aid of additions of polypropylene glycols and their alkyl derivatives or block copolymers in solutions of surfactants. Foaming and foam stability decrease sharply above the cloud points of the solutions due to the foam-inhibiting action of the coacervate phase on the coexisting foam-forming solution. The foam inhibition of polypropylene glycols increases and becomes apparent at lower concentrations with the increase of the average molecular weight of the hydrophobic blocks, the increase of their relative content (in block copolymers with oxyethylene groups), and upon the introduction of alkyl groups.

  8. Performance of some surfactants as wetting agents

    Energy Technology Data Exchange (ETDEWEB)

    Shalaby, M.N.; El-Shanny, O.A.A. [Egyptian Petroleum Research Institute (EPRI), Cairo (Egypt). Evaluation and Analysis Dept.

    2005-12-01

    The wetting power of anionic surfactant: sodium dodecyl sulfate (SDS), and nonionic surfactants: polyoxyethelene(14)monolaurate [La(EO){sub 14}] and polyoxyethelene(14)monoeleate [OI(EO){sub 14}] has been studied to determine their performance as wetting agents. The study reveals that the nonionic compound with a long hydrophobic chain exhibits higher wettability than the shorter one when used at very low cocentrations (below CMC) and the reverse is shown with high concentrations (above CMC). the wetting power of the investigated surfactants increases as the CMC values increases. In case of the nonionic compounds and at surfactant concentrations equal their CMC values, OI(EO){sub 14} shows a higher wetting power than La(EO){sub 14} while is possesses a lower HLB value. The anionic surfactant shows an optimum wetting in comparison with the tested nonionic one. The wettability of all the investigated samples increases as the surface tension of their solutions increases to the allowed limit that can be reached in the presence of surfactant. (orig.)

  9. Small-angle neutron scattering study of aggregate structures of multi-headed pyridinium surfactants in aqueous solution

    Indian Academy of Sciences (India)

    J Haldar; V K Aswal; P S Goyal; S Bhattacharya

    2004-08-01

    The aggregate structures of a set of novel single-chain surfactants bearing one, two and three pyridinium headgroups have been studied using small-angle neutron scattering (SANS). It is found that the nature of aggregate structures of these cationic surfactants depend on the number of headgroups present in the surfactants. The single-headed pyridinium surfactant forms the lamellar structure, whereas surfactants with double and triple headgroups form micelles in water. The aggregates shrink in size with increase in the number of headgroups in the surfactants. The aggregation number () continually decreases and the fractional charge () increases with more number of headgroups on the surfactants. The semimajor axis () and semiminor axis ( = ) of the micelle also decrease with the increase in the number of headgroups in the surfactants. This indicates that hydrocarbon chains in such micelles prepared from multiheaded surfactants adopt bent conformation and no longer stay in extended conformation.

  10. Synthesis of a nano-antibacterial inorganic filler containing a quaternary ammonium salt with long chain alkyl and ;its effect on dental resin composites%含长链烷基季铵盐的纳米抗菌无机填料的合成及其在牙科复合树脂中的应用研究

    Institute of Scientific and Technical Information of China (English)

    吴峻岭; 周凯运; 朱婷; 周传健

    2014-01-01

    目的:设计合成新型的含长链烷基季铵盐的纳米抗菌无机填料,以赋予牙科复合树脂更优良的抗菌性能。方法在分子设计和筛选的基础上,制备了长链烷基季铵盐修饰的纳米抗菌二氧化硅填料,并对填料的抗菌性能进行评价。为进一步提高抗菌填料与树脂的结合力,采用硅烷偶联剂对抗菌填料表面进行了处理,并用红外光谱法对其结构特征进行分析;然后将新型纳米抗菌无机填料加入牙科复合树脂中,观察其在复合树脂基体中的分散情况,同时与商品化的TetricN-Ceram纳米瓷化复合树脂进行对比;并以变异链球菌为对象,研究复合树脂的抗菌性能。结果长链烷基季铵盐成功接枝到纳米二氧化硅颗粒表面;新型纳米抗菌无机填料的抗菌性能优于含短链烷基季铵盐的抗菌无机填料;偶联处理后的纳米抗菌无机填料在树脂基体中分散均匀,与树脂结合紧密,与TetricN-Ceram纳米瓷化复合树脂类似;改性后的复合树脂抗菌性能良好。结论含长链烷基季铵盐的纳米抗菌无机填料抗菌性能良好,经过表面偶联处理后可以很好地与牙科复合树脂共混,提高了牙科复合树脂的抗菌性能。%Objective This study aimed to synthesize a novel nano-antibacterial inorganic filler that contains a quaternary ammonium salt with long chain alkyl and to report the antibacterial property of dental resin composites. Methods A novel nano-antibacterial inorganic filler that contains a quaternary ammonium salt with long chain alkyl was synthesized based on previous research. The antibacterial property of the filler was measured. The surface of the novel nano-antibacterial inorganic filler was modified by a coupling agent to achieve a good interfacial bonding between the filler and the resin matrix. Infrared spectrum analysis was carried out. The modified novel nano-antibacterial inorganic fillers were

  11. A Study on Plasma-Initiated Polymerization of Long Alkyl Chain Methacrylates%甲基丙烯酸长链酯的等离子体引发聚合

    Institute of Scientific and Technical Information of China (English)

    张正彪; 路建美; 程振平; 朱秀林

    2001-01-01

    The polymerization of n-alkyl methacrylate(n=8,12,14) was carried out by means of plasma-initiation. Many factors affecting the polymer conversion and molecular weight have been studied systematically. The polymerization features of the three n-alkyl methacrylates were compared, and the configuration of polymer has been elucidated by NMR. The results indicate that plasma-initiated polymerization not only complies with free-radical mechanism but also has the character of living-polymerization.%研究了甲基丙烯酸正辛酯、甲基丙烯酸正十二酯、甲基丙烯酸正十四酯的等离子体引发本体聚合。考察了各种操作参数对聚合转化率、相对分子质量的影响。并将三种长链酯的聚合情况进行对比,结果表明,随着链长的增加,等离子体引发聚合的活性降低。利用核磁共振测定了聚合物的微观结构,结果与常规自由基加热聚合产物相同。表明等离子体引发聚合是按自由基聚合机理进行的,并具有活性聚合的特征。

  12. Synthesis and Antioxidant Activity of Alkyl Nitroderivatives of Hydroxytyrosol

    Directory of Open Access Journals (Sweden)

    Elena Gallardo

    2016-05-01

    Full Text Available A series of alkyl nitrohydroxytyrosyl ether derivatives has been synthesized from free hydroxytyrosol (HT, the natural olive oil phenol, in order to increase the assortment of compounds with potential neuroprotective activity in Parkinson’s disease. In this work, the antioxidant activity of these novel compounds has been evaluated using Ferric Reducing Antioxidant Power (FRAP, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid diammonium salt (ABTS, and Oxygen Radical Scavenging Capacity (ORAC assays compared to that of nitrohydroxytyrosol (NO2HT and free HT. New compounds showed variable antioxidant activity depending on the alkyl side chain length; compounds with short chains (2–4 carbon atoms maintained or even improved the antioxidant activity compared to NO2HT and/or HT, whereas those with longer side chains (6–8 carbon atoms showed lower activity than NO2HT but higher than HT.

  13. Chemoenzymatic synthesis and properties of novel lactone-type anionic surfactants.

    Science.gov (United States)

    Mori, Keisuke; Matsumura, Shuichi

    2012-01-01

    Two series of lactone-type surfactants with and without a hexyl side chain were prepared by the cyclocondensation of dimethyl alkanedioates with unsaturated diols, such as cis-2-butene-1,4-diol and ricinoleyl alcohol, using a lipase, followed by the addition of hydrophilic 3-mercaptopropionic acid in the presence of triethylamine. The lactone-type surfactants showed clear cmc values and surface tension lowering in aqueous solution irrespective of the hexyl side chain. It was found that the cmc values of lactone-type surfactants were lower than that of typical anionics, e.g., sodium laurate, and the cmc value became lower with increasing size of the lactone ring. The adsorption area at the surface of the aqueous lactone-type surfactant solution was larger when compared to the corresponding non-lactone-type surfactants. Lactone-type surfactants without the hexyl side chain aggregated quickly, forming 3-10 nm micelles; on the other hand, lactone-type surfactants with the hexyl side chain formed significantly larger micelles. This is due to the steric hindrance of the hexyl group on the lactone ring. The solubilization ability of the lactone-type surfactants with a hexyl side chain was superior to those without a hexyl side chain. The lactone-type surfactants showed a high foaming power and low foaming stability. They were also biodegraded by activated sludge.

  14. Surfactants in tribology

    CERN Document Server

    Biresaw, Girma

    2014-01-01

    Surface science and tribology play very critical roles in many industries. Manufacture and use of almost all consumer and industrial products rely on the application of advanced surface and tribological knowledge. The fourth in a series, Surfactants in Tribology, Volume 4 provides an update on research and development activities connecting surfactants and tribological phenomena. Written by renowned subject matter experts, the book demonstrates how improved design of surfactants can be harnessed to control tribological phenomena. Profusely illustrated and copiously referenced, the chapters also

  15. V-shaped crystalline structures of di-n-alkyl esters of phosphoric acid.

    Science.gov (United States)

    Thünemann, Andreas F; Kurth, Dirk G; Beinhoff, Matthias; Bienert, Ralf; Schulz, Burkhard

    2006-06-20

    We prepared crystals of di-n-alkyl esters of phosphoric acid with chain lengths of n = 10, 12, 14, 16, and 18. These were characterized by single-crystal X-ray analysis and differential scanning calorimetry (DSC). It was found that the alkyl chains are in an extended all-trans conformation and aligned close to perpendicular, forming V-shaped molecules. This is in strong contrast to the typical arrangement of the alkyl chains of phospholipids where the two alkyl chains are arranged parallel in the same direction (e.g., tuning fork configuration in bilayers). Additionally, it was found that the arrangement of the V-shaped molecules of the di-n-alkyl esters in neighboring stacks of the lamellar crystals is antiparallel for short chain lengths (n = 10 and 12) and parallel for the longer (n = 14 and 16). DSC reveals that the melting of the crystals increases systematically with increasing chain lengths from 48 to 82 degrees C. The contribution of each methylene group to the melting enthalpy (70-133 kJ/mol) is independent of the chain length (3.9 kJ per mol CH2).

  16. POLYMERIC SURFACTANT STRUCTURE

    Institute of Scientific and Technical Information of China (English)

    P.M. Saville; J.W. White

    2001-01-01

    Polymeric surfactants are amongst the most widespread of all polymers. In nature, proteins and polysaccharides cause self organization as a result of this surfactancy; in industry, polymeric surfactants play key roles in the food, explosives and surface coatings sectors. The generation of useful nano- and micro-structures in films and emulsions as a result of polymer amphiphilicity and the application of mechanical stress is discussed. The use of X-ray and neutron small angle scattering and reflectivity to measure these structures and their dynamic properties will be described. New results on linear and dendritic polymer surfactants are presented.

  17. Dendrimer-surfactant interactions.

    Science.gov (United States)

    Cheng, Yiyun; Zhao, Libo; Li, Tianfu

    2014-04-28

    In this article, we reviewed the interactions between dendrimers and surfactants with particular focus on the interaction mechanisms and physicochemical properties of the yielding dendrimer-surfactant aggregates. In order to provide insight into the behavior of dendrimers in biological systems, the interactions of dendrimers with bio-surfactants such as phospholipids in bulk solutions, in solid-supported bilayers and at the interface of phases or solid-states were discussed. Applications of the dendrimer-surfactant aggregates as templates to guide the synthesis of nanoparticles and in drug or gene delivery were also mentioned.

  18. Surfactant Sector Needs Urgent Readjustment

    Institute of Scientific and Technical Information of China (English)

    Huang Hongzhou

    2007-01-01

    @@ Surfactant industrial system has been basically established After 50 years' development, China has already established a surfactant industrial system with a relatively complete product portfolio and can produce 4714 varieties of surfactants in cationic,anionic, nonionic and amphoteric categories.

  19. Aggregation number-based degrees of counterion dissociation in sodium n-alkyl sulfate micelles.

    Science.gov (United States)

    Lebedeva, Nataly V; Shahine, Antoine; Bales, Barney L

    2005-10-27

    Values of the degree of counterion dissociation, alpha, for sodium n-alkyl sulfate micelles, denoted by SN(c)S, where N(c) is the number of carbon atoms in the alkyl chain, are defined by asserting that the aggregation number, N, is dependent only on the concentration, C(aq), of counterions in the aqueous pseudophase. By using different combinations of surfactant and added salt concentrations to yield the same value of N, alpha can be determined, independent of the experimental method. Electron paramagnetic resonance measurements of the hyperfine spacings of two nitroxide spin probes, 16- and 5-doxylstearic acid methyl ester (16DSE and 5DSE, respectively), are employed to determine whether micelles from two samples have the same value of N to high precision. The EPR spectra are different for the two spin probes, but the values of alpha are the same, within experimental error, as they must be. In agreement with recent work on S12S and with prevailing thought in the literature, values of alpha are constant as a function of N. This implies that the value of alpha is constant whether the surfactant or added electrolyte concentrations are varied. Interestingly, alpha varies with chain length as follows: N(c) = 8, alpha = 0.42 +/- 0.03; N(c) = 9, alpha = 0.41 +/- 0.03; N(c) = 10, alpha = 0.35 +/- 0.02; N(c) = 11, alpha = 0.30 +/- 0.02 at 25 degrees C and N(c) = 13, alpha = 0.22 +/- 0.02; and N(c) = 14, alpha = 0.19 +/- 0.01 at 40 degrees C. A simple electrostatic theoretical description, based on the nonlinear Poisson-Boltzmann equation for the ion distribution around a charged sphere, was compared with the experimental results. The theory predicts values of alpha that are in reasonable agreement with experiment, nicely predicting the decrease of alpha as N(c) increases. However, the theory also predicts that, for a given value of N(c), alpha decreases as N increases. Moreover, this decrease is predicted to be different if N is increased by adding salt or by increasing

  20. Optimization of layered double hydroxide stability and adsorption capacity for anionic surfactants

    NARCIS (Netherlands)

    Schouten, Natasja; Ham, Louis G.J. van der; Euverink, Gert-Jan W.; Haan, André B. de

    2007-01-01

    Low cost adsorption technology offers high potential to clean up laundry rinsing water. From an earlier selection of adsorbents, layered double hydroxide (LDH) proved to be an interesting material for the removal of anionic surfactant, linear alkyl benzene sulfonate (LAS) which is the main contamina

  1. Optimization of layered double hydroxide stability and adsorption capacity for anionic surfactants

    NARCIS (Netherlands)

    Schouten, Natasja; Ham, van der Louis G.J.; Euverink, Gert-Jan W.; Haan, de André B.

    2007-01-01

    Low cost adsorption technology offers high potential to clean up laundry rinsing water. From an earlier selection of adsorbents (Schouten et al. 2007), layered double hydroxide (LDH) proved to be an interesting material for the removal of anionic surfactant, linear alkyl benzene sulfonate (LAS) whic

  2. SYNTHESIS AND PHYSICAL-PROPERTIES OF HIGHLY CA2+- TOLERANT DISODIUM 2-(SULFATOMETHYL)-1-ALKYLSULFATE SURFACTANTS

    NARCIS (Netherlands)

    KOOREMAN, PA; ENGBERTS, JBFN

    1994-01-01

    The synthesis, critical micelle concentrations (CMC) and Krafft temperatures (T(Krafft)) of a series of disodium 2-(sulfatomethyl)-1-alkylsulfates (2a-d) are presented, with alkyl being n-tetradecyl (C-14), n-hexadecyl (C-16), n-octadecyl (C18) and n-eicosyl(C20). The surfactants exhibit a large Ca2

  3. Effects of concentration, head group, and structure of surfactants on the degradation of phenanthrene

    Energy Technology Data Exchange (ETDEWEB)

    Jin Danyue; Jiang Xia [State Environmental Protect Key Laboratory of Lake Eutrophication Control, Research Center of Lake Environment, Chinese Research Academy of Environmental Science, No. 8 Dayangfang, An Wai Bei Yuan, Beijing 100012 (China)]. E-mail: jiangxia@craes.org.cn; Jing Xin [State Environmental Protect Agency of China (China); Ou Ziqing [Institute of Applied Ecology, Chinese Academy of Science, Shenyang 110016 (China)

    2007-06-01

    The effects of concentration, polar/ionic head group, and structure of surfactants on the biodegradation of polycyclic aromatic hydrocarbons (PAHs) in the aqueous phase, as well as their effects on the bacterial activity were investigated. The toxicity ranking of studied surfactants is: non-ionic surfactants (Tween 80, Brij30, 10LE and Brij35) < anionic surfactants (LAS) < cationic surfactants (TDTMA). For the same head group and similar molecular structure, the toxicity to the bacteria is due to the chain length, in which the toxicity becomes lower as the chain length increases. The bacterial growth increased slightly when phenanthrene and LAS ({<=}10 mg L{sup -1}) served the sole carbon and energy resource. However, the degradation of {sup 14}C-phenanthrene showed either a decrease or no obvious change with the surfactants present at all tested concentrations (5-40 mg L{sup -1}). Thus, the surfactant addition is not beneficial to the removal of phenanthrene or other PAH contaminants due presumably to the preferential utilization of surfactants at low levels as the non-toxic nutrient resource and to the high toxicity of the surfactants at high levels to the microorganism activity. Biodegradation of phenanthrene was also influenced by the surfactant concentration, head group type, and structure. Much more research has yet to be completed on the use of surfactants for soil remediation due to the surfactant toxicity or biodegradation effect.

  4. Cationic vesicles based on non-ionic surfactant and synthetic aminolipids mediate delivery of antisense oligonucleotides into mammalian cells.

    Science.gov (United States)

    Grijalvo, Santiago; Alagia, Adele; Puras, Gustavo; Zárate, Jon; Pedraz, Jose Luis; Eritja, Ramon

    2014-07-01

    A formulation based on a synthetic aminolipid containing a double-tailed with two saturated alkyl chains along with a non-ionic surfactant polysorbate-80 has been used to form lipoplexes with an antisense oligonucleotide capable of inhibiting the expression of Renilla luciferase mRNA. The resultant lipoplexes were characterized in terms of morphology, Zeta potential, average size, stability and electrophoretic shift assay. The lipoplexes did not show any cytotoxicity in cell culture up to 150 mM concentration. The gene inhibition studies demonstrated that synthetic cationic vesicles based on non-ionic surfactant and the appropriate aminolipid play an important role in enhancing cellular uptake of antisense oligonucleotides obtaining promising results and efficiencies comparable to commercially available cationic lipids in cultured mammalian cells. Based on these results, this amino lipid moiety could be considered as starting point for the synthesis of novel cationic lipids to obtain potential non-viral carriers for antisense and RNA interference therapies. Copyright © 2014 Elsevier B.V. All rights reserved.

  5. Stratum corneum lipid removal by surfactants: relation to in vivo irritation.

    Science.gov (United States)

    Froebe, C L; Simion, F A; Rhein, L D; Cagan, R H; Kligman, A

    1990-01-01

    The relationship between the in vivo irritation potential of sodium lauryl sulfate (SLS) and linear alkyl benzene sulfonate (LAS) and the ability of these two surfactants to remove lipid from the stratum corneum (SC) in vitro were investigated. Either surfactant removes detectable levels of lipids only above its critical micelle concentration (CMC). At high concentrations the surfactants removed only very small amounts of cholesterol, free fatty acid, the esters of those materials, and possibly squalene. SLS and LAS have been shown, below the CMC, to bind to and irritate the SC. Thus, clinical irritation provoked by SLS or LAS is unlikely to be directly linked with extraction of SC lipid. The milder forms of irritation--dryness, tightness, roughness--may involve both surfactant binding to and denaturation of keratin as well as disruption of lipid. Our findings challenge earlier assumptions that surfactants' degreasing of the SC is involved in the induction of erythema.

  6. Synthesis and catalysis property of Gemini surfactants with ester based long-chain fatty alcohol%含长链脂肪醇酯基双子表面活性剂合成及催化性能

    Institute of Scientific and Technical Information of China (English)

    丁效明; 潘忠稳; 何领; 李凯波; 刘玉莹

    2012-01-01

    Three Gemini surfactants (C12, C14, C16) with ester based long-chain fatty alcohol were prepared by reacting bis ( ( dimethylamino) methyl) phthalate with dodecyl 2 - chloroacetate, tetradecyl 2 -chloroacetate and hexadecyl 2-chloroacetate respectively with 80% yield in acetone for refluxing 36 h . The purity was measured by two-phase chemical titration analysis, and the critical micelle concentration (CMC) values were 2.6×l0-4, 3.6×l0-5, 8.02×l0-6 by measuring the electrical conductivity. The phase transfer catalysis property of (C16) was studied by reaction of 4-methyl benzyl chloride with sodium acetate. It was founded that C16 had good catalysis property when reaction activation energy ( Ea) was 18. 59 kJ · mol-1 lower than the blank at C b =0.004 394 mol · L-1.%以丙酮为溶剂,二(二甲基胺基乙基)邻苯二甲酸酯分别与氯乙酸正十二醇酯、氯乙酸正十四醇酯及氯乙酸正十六醇酯回流反应36 h,得到3种含长链脂肪醇酯基季铵盐双子表面活性剂C12、C14、C16,收率80%.采用两相滴定法测定了其纯度,采用电导法测定了其CMC值分别是2.6× 10-4、3.6×10-5,8.02× 10-6.在无水乙酸钠与对甲基氯苄反应中,研究了C16的催化性能.当其浓度为0.004 394 mol·L-1,该反应活化能(Ea)相对于不加催化剂降低了18.59 kJ·mol-1,具有良好的催化性能.

  7. Correlation of Critical Micelle Concentration of Sodium Alkyl Benzenesulfonates with Molecular Descriptors

    Institute of Scientific and Technical Information of China (English)

    2006-01-01

    The hydrophobic-hydrophilic segment geometries of 36 sodium alkyl benzenesulfonates were fully optimized and calculated by abini-tio RHF/6-31G(d), quantum chemical data such as the charge density, the energy of molecular orbital and the dipole moment were obtained. Based on two topological descriptors and one quantum chemical descriptor, a significant quantitative structure-property relationship (QSPR) model for the critical micelle concentration (cmc) of sodium alkyl benzenesulfonate surfactants was obtained by using the multiple linear regression technique. The good correlation coefficient of R2 (0.980) and cross-validation correlation coefficient R2cv (0.974) indicate the excellent capability and stability of the regression equation developed. In addition, linear relationships between logarithm of cmc and the dipole moment of surfactant hydrophobic hydrophilic segments for each homologous series have also been established with high correlation coefficient.

  8. Binary functionalization of H:Si(111) surfaces by alkyl monolayers with different linker atoms enhances monolayer stability and packing.

    Science.gov (United States)

    Arefi, Hadi H; Nolan, Michael; Fagas, Giorgos

    2016-05-14

    Alkyl monolayer modified Si forms a class of inorganic-organic hybrid materials with applications across many technologies such as thin-films, fuel/solar-cells and biosensors. Previous studies have shown that the linker atom, through which the monolayer binds to the Si substrate, and any tail group in the alkyl chain, can tune the monolayer stability and electronic properties. In this paper we study the H:Si(111) surface functionalized with binary SAMs: these are composed of alkyl chains that are linked to the surface by two different linker groups. Aiming to enhance SAM stability and increase coverage over singly functionalized Si, we examine with density functional theory simulations that incorporate vdW interactions, a range of linker groups which we denote as -X-(alkyl) with X = CH2, O(H), S(H) or NH(2) (alkyl = C6 and C12 chains). We show how the stability of the SAM can be enhanced by adsorbing alkyl chains with two different linkers, e.g. Si-[C, NH]-alkyl, through which the adsorption energy is increased compared to functionalization with the individual -X-alkyl chains. Our results show that it is possible to improve stability and optimum coverage of alkyl functionalized SAMs linked through a direct Si-C bond by incorporating alkyl chains linked to Si through a different linker group, while preserving the interface electronic structure that determines key electronic properties. This is important since any enhancement in stability and coverage to give more densely packed monolayers will result in fewer defects. We also show that the work function can be tuned within the interval of 3.65-4.94 eV (4.55 eV for bare H:Si(111)).

  9. The hydrophobicity of silicone-based oils and surfactants and their use in reactive microemulsions.

    Science.gov (United States)

    Castellino, Victor; Cheng, Yu-Ling; Acosta, Edgar

    2011-01-01

    In this work, for the first time, the Hydrophilic-Lipophilic Difference (HLD) framework for microemulsion formulation has been applied to silicone oils and silicone alkyl polyether surfactants. Based on the HLD equations and recently introduced mixing rules, we have quantified the hydrophobicity of the oils according to the equivalent alkane carbon number (EACN). We have found that, in a reference system containing sodium dihexyl sulfosuccinate (SDHS) as the surfactant, 0.65 centistoke (cSt) and 3.0 cSt silicone oils behave like n-dodecane and n-pentadecane, respectively. Silicone alkyl polyether surfactants were found to have characteristic curvatures ranging 3.4-18.9, exceeding that of most non-ionic surfactants. The introduction of methacrylic acid (MAA) and hydroxyethyl methacrylate (HEMA) to the aqueous phase caused a significant negative shift in HLD, indicative of an aqueous phase that is less hydrophilic than pure water. The more hydrophobic surfactants (largest positive curvatures) were used in order to compensate for this effect. These findings have led to the formulation of bicontinuous microemulsions (μEs) containing silicone oil, silicone alkyl polyether and reactive monomers in aqueous solution. Ternary phase diagrams of these systems revealed the potential for silicone-containing polymer composites with bicontinuous morphologies. These findings have also helped to explain the phase behavior of formulations previously reported in literature, and could help in providing a systematic, consistent approach to future silicone oil based microemulsion formulation.

  10. SURFACTANTS IN LUBRICATION

    Science.gov (United States)

    Surfactants are one of the most widely applied materials by consumers and industry. The application areas for surfactants span from everyday mundane tasks such as cleaning, to highly complex processes involving the formulation of pharmaceuticals, foods, pesticides, lubricants, etc. Even though sur...

  11. Dynamic covalent surfactants

    NARCIS (Netherlands)

    Minkenberg, C.B.

    2012-01-01

    In this thesis the development of surfactant aggregates with fast exchange dynamics between the aggregated and non-aggregated state is described. Dynamic surfactant exchange plays an important role in natural systems, for instance in cell signaling, cell division, and uptake and release of cargo. Re

  12. Mild Catalytic methods for Alkyl-Alkyl Bond Formation

    Energy Technology Data Exchange (ETDEWEB)

    Vicic, David A

    2009-08-10

    Overview of Research Goals and Accomplishments for the Period 07/01/06 – 06/30/07: Our overall research goal is to transform the rapidly emerging synthetic chemistry involving alkyl-alkyl cross-couplings into more of a mechanism-based field so that that new, rationally-designed catalysts can be performed under energy efficient conditions. Our specific objectives for the previous year were 1) to obtain a proper electronic description of an active catalyst for alkyl-alkyl cross-coupling reactions and 2) to determine the effect of ligand structure on the rate, scope, selectivity, and functional group compatibility of C(sp3)-C(sp3) cross-coupling catalysis. We have completed both of these initial objectives and established a firm base for further studies. The specific significant achievements of the current grant period include: 1) we have performed magnetic and computational studies on (terpyridine)NiMe, an active catalyst for alkyl-alkyl cross couplings, and have discovered that the unpaired electron resides heavily on the terpyridine ligand and that the proper electronic description of this nickel complex is a Ni(II)-methyl cation bound to a reduced terpyridine ligand; 2) we have for the first time shown that alkyl halide reduction by terpyridyl nickel catalysts is substantially ligand based; 3) we have shown by isotopic labeling studies that the active catalyst (terpyridine)NiMe is not produced via a mechanism that involves the formation of methyl radicals when (TMEDA)NiMe2 is used as the catalyst precursor; 4) we have performed an extensive ligand survey for the alkyl-alkyl cross-coupling reactions and have found that electronic factors only moderately influence reactivity in the terpyridine-based catalysis and that the most dramatic effects arise from steric and solubility factors; 5) we have found that the use of bis(dialkylphosphino)methanes as ligands for nickel does not produce active catalysts for cross-coupling but rather leads to bridging hydride

  13. New theoretical framework for designing nonionic surfactant mixtures that exhibit a desired adsorption kinetics behavior.

    Science.gov (United States)

    Moorkanikkara, Srinivas Nageswaran; Blankschtein, Daniel

    2010-12-21

    How does one design a surfactant mixture using a set of available surfactants such that it exhibits a desired adsorption kinetics behavior? The traditional approach used to address this design problem involves conducting trial-and-error experiments with specific surfactant mixtures. This approach is typically time-consuming and resource-intensive and becomes increasingly challenging when the number of surfactants that can be mixed increases. In this article, we propose a new theoretical framework to identify a surfactant mixture that most closely meets a desired adsorption kinetics behavior. Specifically, the new theoretical framework involves (a) formulating the surfactant mixture design problem as an optimization problem using an adsorption kinetics model and (b) solving the optimization problem using a commercial optimization package. The proposed framework aims to identify the surfactant mixture that most closely satisfies the desired adsorption kinetics behavior subject to the predictive capabilities of the chosen adsorption kinetics model. Experiments can then be conducted at the identified surfactant mixture condition to validate the predictions. We demonstrate the reliability and effectiveness of the proposed theoretical framework through a realistic case study by identifying a nonionic surfactant mixture consisting of up to four alkyl poly(ethylene oxide) surfactants (C(10)E(4), C(12)E(5), C(12)E(6), and C(10)E(8)) such that it most closely exhibits a desired dynamic surface tension (DST) profile. Specifically, we use the Mulqueen-Stebe-Blankschtein (MSB) adsorption kinetics model (Mulqueen, M.; Stebe, K. J.; Blankschtein, D. Langmuir 2001, 17, 5196-5207) to formulate the optimization problem as well as the SNOPT commercial optimization solver to identify a surfactant mixture consisting of these four surfactants that most closely exhibits the desired DST profile. Finally, we compare the experimental DST profile measured at the surfactant mixture condition

  14. Nanoparticle decoration with surfactants: Molecular interactions, assembly, and applications

    Science.gov (United States)

    Heinz, Hendrik; Pramanik, Chandrani; Heinz, Ozge; Ding, Yifu; Mishra, Ratan K.; Marchon, Delphine; Flatt, Robert J.; Estrela-Lopis, Irina; Llop, Jordi; Moya, Sergio; Ziolo, Ronald F.

    2017-02-01

    Nanostructures of diverse chemical nature are used as biomarkers, therapeutics, catalysts, and structural reinforcements. The decoration with surfactants has a long history and is essential to introduce specific functions. The definition of surfactants in this review is very broad, following its lexical meaning ;surface active agents;, and therefore includes traditional alkyl modifiers, biological ligands, polymers, and other surface active molecules. The review systematically covers covalent and non-covalent interactions of such surfactants with various types of nanomaterials, including metals, oxides, layered materials, and polymers as well as their applications. The major themes are (i) molecular recognition and noncovalent assembly mechanisms of surfactants on the nanoparticle and nanocrystal surfaces, (ii) covalent grafting techniques and multi-step surface modification, (iii) dispersion properties and surface reactions, (iv) the use of surfactants to influence crystal growth, as well as (v) the incorporation of biorecognition and other material-targeting functionality. For the diverse materials classes, similarities and differences in surfactant assembly, function, as well as materials performance in specific applications are described in a comparative way. Major factors that lead to differentiation are the surface energy, surface chemistry and pH sensitivity, as well as the degree of surface regularity and defects in the nanoparticle cores and in the surfactant shell. The review covers a broad range of surface modifications and applications in biological recognition and therapeutics, sensors, nanomaterials for catalysis, energy conversion and storage, the dispersion properties of nanoparticles in structural composites and cement, as well as purification systems and classical detergents. Design principles for surfactants to optimize the performance of specific nanostructures are discussed. The review concludes with challenges and opportunities.

  15. Cs/B 催化剂载体对甲苯甲醇侧链烷基化性能的影响%The Effect of Different Carrier Supported Cs and B Catalysts on Catalytic Performances for Side_chain Alkylation of Toluene and Methanol

    Institute of Scientific and Technical Information of China (English)

    田晓龙; 王斌; 栾春晖; 黄伟

    2015-01-01

    以间苯二酚、甲醛为碳源合成的有序介孔碳(OMC)为载体,采用浸渍法制备了含Cs和B的负载型催化剂(CsB/OMC)。对其与不同载体改性催化剂的甲醇甲苯侧链烷基化性能进行了对比研究。采用XRD、CO2_T PD、N H3_T PD、氮吸附_脱附、T EM 等手段对催化剂进行了表征。实验结果发现,不同载体催化剂的甲苯甲醇侧链烷基化活性顺序由大到小依次为:CsB/OMC , CsB/MCM_41,CsB/AC ,CsB/ZSM_5.其中,CsB/OMC 活性最高,乙苯和苯乙烯的总收率可达到34.9%;C sB/M C M_41中苯乙烯的选择性较高。研究表明,弱碱中心有利于提高侧链烷基化活性,弱酸中心和中强碱中心的协同作用有利于提高苯乙烯的选择性。%Ordered mesoporous carbon supported Cs and B catalysts (CsB/OMC) were pre_pared by impregnation of Cs and B components on OMC carrier ,which was synthesized by a two_step method of soft template using resorcinol and formaldehyde as carbon precursor ,triblock co_polymer Pluronic F127 as template .The catalytic performances were investigated and compared for side chain alkylation of toluene with methanol over the different carriers modified catalysts . The catalysts were characterized by X_ray diffraction (XRD) ,nitrogen adsorption_desorption iso_therm ,transmission electron microscopy (TEM ) ,temperature programmed desorption of CO2 (CO2_TPD) and temperature programmed desorption of NH3 (NH3_TPD) .The catalytic perform_ances and characterization results of different carriers modified catalysts were compared .It reveals that catalytic activity of side chain alkylation decreases in the order CsB/OMC ,CsB/MCM_41 , CsB/AC ,CsB/ZSM_5 ,and the yield of ethylbenzene and styrene (YSTY+ EB ) reaches 34.9% over the CsB/OMC .The weak base sites can help improve the side chain alkylation catalytic activity , and the high styrene selectivity requires coordination of appropriate weak acid and weak

  16. Phase behavior, rheological property, and transmutation of vesicles in fluorocarbon and hydrocarbon surfactant mixtures.

    Science.gov (United States)

    Yuan, Zaiwu; Qin, Menghua; Chen, Xiushan; Liu, Changcheng; Li, Hongguang; Hao, Jingcheng

    2012-06-26

    (19)F NMR as well as (31)P NMR measurements. Upon replacement of NFDA by DEHPA, the signal from the (19)F atoms adjacent to the hydrophilic headgroup disappears and that from the (19)F atoms on the main chain becomes sharper. This could be interpreted as an increase of microfluidity in the mixed vesicle bilayers at higher content of DEHPA, whose alkyl chains are expected to have a lower chain melting point. Our results provide basic knowledge on vesicle formation and their structural evolution in salt-free catanionic surfactant systems containing mixed ion pairs, which may contribute to a deeper understanding of the rules governing the formation and properties of surfactant self-assembly.

  17. Helsingør Statement on poly- and perfluorinated alkyl substances (PFASs)

    DEFF Research Database (Denmark)

    Scheringer, Martin; Trier, Xenia; Cousins, Ian T.

    2014-01-01

    In this discussion paper, the transition from long-chain poly- and perfluorinated alkyl substances (PFASs) to fluorinated alternatives is addressed. Long-chain PFASs include perfluoroalkyl carboxylic acids (PFCAs) with 7 or more perfluorinated carbons, perfluoroalkyl sulfonic acids (PFSAs) with 6...

  18. Layer-by-Layer Assembly of Fluorine-Free Polyelectrolyte-Surfactant Complexes for the Fabrication of Self-Healing Superhydrophobic Films.

    Science.gov (United States)

    Wu, Mengchun; An, Ni; Li, Yang; Sun, Junqi

    2016-11-29

    Fluorine-free self-healing superhydrophobic films are of significance for practical applications because of their extended service life and cost-effective and eco-friendly preparation process. In this study, we report the fabrication of fluorine-free self-healing superhydrophobic films by layer-by-layer (LbL) assembly of poly(sodium 4-styrenesulfonate) (PSS)-1-octadecylamine (ODA) complexes (PSS-ODA) and poly(allylamine hydrochloride) (PAH)-sodium dodecyl sulfonate (SDS) (PAH-SDS) complexes. The wettability of the LbL-assembled PSS-ODA/PAH-SDS films depends on the film structure and can be tailored by changing the NaCl concentration in aqueous dispersions of PSS-ODA complexes and the number of film deposition cycles. The freshly prepared PSS-ODA/PAH-SDS film with micro- and nanoscaled hierarchical structures is hydrophilic and gradually changes to superhydrophobic in air because the polyelectrolyte-complexed ODA and SDS surfactants tend to migrate to the film surface to cover the film with hydrophobic alkyl chains to lower its surface energy. The large amount of ODA and SDS surfactants loaded in the superhydrophobic PSS-ODA/PAH-SDS films and the autonomic migration of these surfactants to the film surface endow the resultant superhydrophobic films with an excellent self-healing ability to restore the damaged superhydrophobicity. The self-healing superhydrophobic PSS-ODA/PAH-SDS films are mechanically robust and can be deposited on various flat and nonflat substrates. The LbL assembly of oppositely charged polyelectrolyte-surfactant complexes provides a new way for the fabrication of fluorine-free self-healing superhydrophobic films with satisfactory mechanical stability, enhanced reliability, and extended service life.

  19. Tilting and Tumbling in Transmembrane Anion Carriers: Activity Tuning through n‐Alkyl Substitution

    OpenAIRE

    Edwards, Sophie J.; Marques, Igor; Dias, Christopher M.; Tromans, Robert A.; Lees, Nicholas R; Félix, Vítor; Valkenier, Hennie; Davis, Anthony P

    2016-01-01

    Abstract Anion transport by synthetic carriers (anionophores) holds promise for medical applications, especially the treatment of cystic fibrosis. Among the factors which determine carrier activity, the size and disposition of alkyl groups is proving remarkably important. Herein we describe a series of dithioureidodecalin anionophores, in which alkyl substituents on one face are varied from C0 to C10 in two‐carbon steps. Activities increase then decrease as the chain length grows, peaking qui...

  20. Surfactants in the environment.

    Science.gov (United States)

    Ivanković, Tomislav; Hrenović, Jasna

    2010-03-01

    Surfactants are a diverse group of chemicals that are best known for their wide use in detergents and other cleaning products. After use, residual surfactants are discharged into sewage systems or directly into surface waters, and most of them end up dispersed in different environmental compartments such as soil, water or sediment. The toxic effects of surfactants on various aquatic organisms are well known. In general, surfactants are present in the environment at levels below toxicity and in Croatia below the national limit. Most surfactants are readily biodegradable and their amount is greatly reduced with secondary treatment in wastewater treatment plants. The highest concern is the release of untreated wastewater or wastewater that has undergone primary treatment alone. The discharge of wastewater polluted with massive quantities of surfactants could have serious effects on the ecosystem. Future studies of surfactant toxicities and biodegradation are necessary to withdraw highly toxic and non-biodegradable compounds from commercial use and replace them with more environmentally friendly ones.

  1. Aggregation Behavior of Long-Chain Piperidinium Ionic Liquids in Ethylammonium Nitrate

    Directory of Open Access Journals (Sweden)

    Caili Dai

    2014-12-01

    Full Text Available Micelles formed by the long-chain piperidinium ionic liquids (ILs N-alkyl-N-methylpiperidinium bromide of general formula CnPDB (n = 12, 14, 16 in ethylammonium nitrate (EAN were investigated through surface tension and dissipative particle dynamics (DPD simulations. Through surface tension measurements, the critical micelle concentration (cmc, the effectiveness of surface tension reduction (Πcmc, the maximum excess surface concentration (Гmax and the minimum area occupied per surfactant molecule (Amin can be obtained. A series of thermodynamic parameters (DG0 m, DH0 m and DS0 m of micellization can be calculated and the results showed that the micellization was entropy-driven. In addition, the DPD simulation was performed to simulate the whole aggregation process behavior to better reveal the micelle formation process.

  2. Pulmonary surfactant and lung transplantation

    NARCIS (Netherlands)

    Erasmus, Michiel Elardus

    1997-01-01

    Pulmonary surfactant lowers the surface tension at the air-water interface inside the alveolus. This is achieved by adsorption of surfactant phospholipids at the air-water interface, a process controlled by surfactant-associated proteins, such as SP-A. In this way, surfactant prevents collapse of th

  3. Metathesis depolymerizable surfactants

    Science.gov (United States)

    Jamison, Gregory M.; Wheeler, David R.; Loy, Douglas A.; Simmons, Blake A.; Long, Timothy M.; McElhanon, James R.; Rahimian, Kamyar; Staiger, Chad L.

    2008-04-15

    A class of surfactant molecules whose structure includes regularly spaced unsaturation in the tail group and thus, can be readily decomposed by ring-closing metathesis, and particularly by the action of a transition metal catalyst, to form small molecule products. These small molecules are designed to have increased volatility and/or enhanced solubility as compared to the original surfactant molecule and are thus easily removed by solvent extraction or vacuum extraction at low temperature. By producing easily removable decomposition products, the surfactant molecules become particularly desirable as template structures for preparing meso- and microstructural materials with tailored properties.

  4. Synthesis and Antioxidant Activity of Hydroxytyrosol Alkyl-Carbonate Derivatives.

    Science.gov (United States)

    Fernandez-Pastor, Ignacio; Fernandez-Hernandez, Antonia; Rivas, Francisco; Martinez, Antonio; Garcia-Granados, Andres; Parra, Andres

    2016-07-22

    Three procedures have been investigated for the isolation of tyrosol (1) and hydroxytyrosol (2) from a phenolic extract obtained from the solid residue of olive milling. These three methods, which facilitated the recovery of these phenols, were chemical or enzymatic acetylation, benzylation, and carbomethoxylation, and subsequent carbonylation or acetonation reactions. Several new lipophilic alkyl-carbonate derivatives of hydroxytyrosol have been synthesized, coupling the primary hydroxy group of this phenol, through a carbonate linker, using alcohols with different chain lengths. The antioxidant properties of these lipophilic derivatives have been evaluated by different methods and compared with free hydroxytyrosol (2) and also with the well-known antioxidants BHT and α-tocopherol. Three methods were used for the determination of this antioxidant activity: FRAP and ABTS assays, to test the antioxidant power in hydrophilic media, and the Rancimat test, to evaluate the antioxidant capacity in a lipophilic matrix. These new alkyl-carbonate derivatives of hydroxytyrosol enhanced the antioxidant activity of this natural phenol, with their antioxidant properties also being higher than those of the commercial antioxidants BHT and α-tocopherol. There was no clear influence of the side-chain length on the antioxidant properties of the alkyl-carbonate derivatives of 2, although the best results were achieved mainly by the compounds with a longer chain on the primary hydroxy group of this natural phenolic substance.

  5. Application of disorganized monolayer films on gold electrodes to the prevention of surfactant inhibition of the voltammetric detection of trace metals via anodic stripping of underpotential deposits: detection of copper.

    Science.gov (United States)

    Herzog, Grégoire; Arrigan, Damien W M

    2003-01-15

    Development of an approach to prevention of electrode surface fouling by surfactants in samples is demonstrated. Spontaneously adsorbed monolayer systems employing short alkyl chains and bulky end groups are used to form porous disorganized monolayers on gold electrodes. Detection of copper by stripping of underpotential deposits formed at electrodes modified with disorganized films of mercaptoethanesulfonate (MES), mercaptopropanesulfonate, mercaptoacetic acid, and mercaptopropanoic acid was possible, and to a much lesser extent at aminoethanethiol and L-cysteine films. Use of short deposition times in conjunction with linear sweep anodic stripping voltammetry allowed detection of Cu2+ ions down to 1 x 10(-6) M in sulfuric acid solution, using underpotential deposition as the deposition step of the procedure. Calibration graphs were linear in the concentration range (1-80) x 10(-6) M Cu2+ using 15-s deposition at 0.00 V versus Ag/AgCl. The surfactants Tween 20, Tween 80, and Triton X-100 were found to have no affect on detection of Cu2+ ions in the calibration curve concentration range using MES-modified gold electrodes, whereas at unmodified gold electrodes very severe attenuation of the detection capability was manifested. The average slope for all calibration curves at the MES-modified electrode in the absence and presence of the surfactants at two different concentration levels was 0.0710 +/- 0.0024 microA microM(-1); in contrast, the slope of the calibration line at uncoated gold electrodes in the presence of surfactant was 0.0268 microA microM(-1). These results indicate the excellent ability of a disorganized, porous monolayer for prevention of fouling of the electrode surface by the surfactants.

  6. Preparation and evaluation of some amide ether carboxylate surfactants

    Directory of Open Access Journals (Sweden)

    M.M.A. El-Sukkary

    2012-06-01

    Full Text Available A homologous series of new mild surfactants, namely: Alkyl amide ether carboxylates surfactants (AEC RCO–NHCH2CH2O (CH2CH2O6CH2COONa, were synthesized by esterification, amidation, ethoxylation and carboxymethylation reaction steps of fatty acids (Lauric, Myristic, palmitic, stearic, oleic or linoleic. The chemical structures of the prepared compounds were confirmed using different spectroscopic techniques, FTIR spectroscopy, mass spectra and HNMR. The surface properties including surface and interfacial tensions, foaming height, emulsification power, calcium ion stability, stability to hydrolysis and critical micelle concentration (cmc were determined. The study of their surface properties showed their stability in hard water and in acidic and alkaline media. These compounds have high calcium ion stability. The low foaming power could have an application in the dyeing auxiliary industry. The lower values of the interfacial tension values indicate the ability of using these surfactants in several applications as corrosion inhibitors and biocides. The data revealed various advantages and potentials as a main surfactant as well as co- surfactants.

  7. Diester-containing Zwitterionic Gemini Surfactants with Different Spacer and Its Impact on Micellization Properties and Viscosity of Aqueous Micellar Solution.

    Science.gov (United States)

    Patil, Sachin Vasant; Patil, Sanyukta Arun; Pratap, Amit Prabhakar

    2016-09-01

    A series of diester containing zwitterionic gemini surfactants, N,N-dimethyl-N-alkyl-2-[[hydroxy (alkoxy) phosphinyl]oxy]-alkylammonium designated as C8(-)-S-Cn(+), S = 2 and 3, n = 12, 14 and 16, were synthesized and characterized by instrumental techniques namely FT-IR, (1)H NMR, (13)C NMR, (31)P NMR and Mass spectral studies. These new gemini surfactants further investigated for their various surfactant properties. The critical micelle concentration (cmc) and the effectiveness of surface tension reduction (Πcmc) were determined as a function of surfactant concentration by means of surface tension measurement. Micellization and viscosity properties were investigated by surface tension, electrical conductivity, dye micellization and rheology techniques. The findings of the aqueous surfactant system obtained were impacted by polarity, size and the nature of zwitterions as the surface. The thermodynamic and viscosity properties of these surfactants found to be based on the structures of gemini surfactants.

  8. Biobased surfactant-like molecules from organic wastes: the effect of waste composition and composting process on surfactant properties and on the ability to solubilize Tetrachloroethene (PCE).

    Science.gov (United States)

    Quadri, Giorgia; Chen, Xiaosong; Jawitz, James W; Tambone, Fulvia; Genevini, Pierluigi; Faoro, Franco; Adani, Fabrizio

    2008-04-01

    In this work, four surfactant-like humic acids (HAs) obtained from garden lignocellulose wastes and kitchen food wastes mixed with garden-lignocellulose wastes, both before and after composting, were tested for surfactant properties and the ability to solubilize tetrachloroethene (PCE). The waste-derived HAs showed good surfactant properties, lowering the water surface tension from 74 mN m(-1) to 45.4 +/- 4.4 mN m(-1), with a critical micelle concentration (CMC) of 1.54 +/- 1.68 g L(-1), which is lower than many synthetic ionic surfactants. CMC was affected by both waste origin and composting processes. The addition of food waste and composting reduced CMC by adding alkyl-C (measured by CP MAS 13C NMR) and N- and S-HA contents (amide molecules), so that a multistep regression was found [CMC = 24.6 - 0.189 alkyl C - 2.64 (N + S); R2 = 0.77, P < 0.10, n = 6]. The four HAs solubilized PCE at the rate of 0.18-0.47 g PCE/g aqueous biosurfactant. These results were much higher than those reported in the literature for a commercial HA (0.026 g/g), but they were in line with those measured in this work for nonionic surfactants such as Tween-80 (0.69 g/g) and Triton X-100 (1.08 g/g).

  9. 77 FR 72747 - Alkyl(C8

    Science.gov (United States)

    2012-12-06

    ... ) dimethylamidopropylamines where the alkyl group is linear and may be saturated and/or unsaturated when used as an inert... for residues of the N- alkyl(C 8 -C 18 ) dimethylamidopropylamines where the alkyl group is linear and... value of 100 ppb based on screening level modeling was used to assess the contribution to drinking water...

  10. MICROWAVE IRRADIATED ALKYLATION OF DIETHYL ACETAMIDOMALONATE

    Institute of Scientific and Technical Information of China (English)

    张雅文; 沈宗旋; 陆军

    1995-01-01

    Ethyl acetamidomalonate was alkylated using three alkylating agents, both by microtwave irradiation of a mixture of the malonate,the alkylating agent, potassium carbonate,TEBA,and DMF for 0.5 to 1.5 min and by heating a solution of the malonate, sodium ethoxide, and the alkylatlng agent in ethanol for several hours. The two metlmds gave comparable results.

  11. 40 CFR 721.9892 - Alkylated urea.

    Science.gov (United States)

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkylated urea. 721.9892 Section 721... Alkylated urea. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as an alkylated urea (PMN P-93-1649) is subject to reporting under...

  12. Different hydrogen-bonded chains in the crystal structures of three alkyl N-[(E-1-(2-benzylidene-1-methylhydrazinyl-3-hydroxy-1-oxopropan-2-yl]carbamates

    Directory of Open Access Journals (Sweden)

    Thais C. M. Noguiera

    2015-07-01

    Full Text Available The crystal structures of three methylated hydrazine carbamate derivatives prepared by multi-step syntheses from l-serine are presented, namely benzyl N-{(E-1-[2-(4-cyanobenzylidene-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C20H20N4O4, tert-butyl N-{(E-1-[2-(4-cyanobenzylidene-1-methylhydrazinyl]-3-hydroxy-1-oxopropan-2-yl}carbamate, C17H22N4O4, and tert-butyl N-[(E-1-(2-benzylidene-1-methylhydrazinyl-3-hydroxy-1-oxopropan-2-yl]carbamate, C16H23N3O4. One of them shows that an unexpected racemization has occurred during the mild-condition methylation reaction. In each crystal structure, the molecules are linked into chains by O—H...O hydrogen bonds, but with significant differences between them.

  13. Perfluorinated Alcohols Induce Complex Coacervation in Mixed Surfactants.

    Science.gov (United States)

    Jenkins, Samuel I; Collins, Christopher M; Khaledi, Morteza G

    2016-03-15

    Recently, we reported a unique and nearly ubiquitous phenomenon of inducing simple and complex coacervation in solutions of a broad variety of individual and mixed amphiphiles and over a wide range of concentrations and mole fractions. This paper describes a novel type of biphasic separation in aqueous solutions of mixed cationic-anionic (catanionic) surfactants induced by hexafluoroisopropanol (HFIP). The test cases included mixtures of cetyltrimethylammonium bromide (CTAB) and sodium dodecyl sulfate (SDS) (surfactants with different carbon chain lengths) as well as dodecyltrimethylammonium bromide (DTAB) with SDS (surfactants with the same carbon chain lengths). The CTAB-SDS-HFIP coacervate systems can be produced at many different mole ratios of surfactant, but DTAB-SDS-HFIP formed only coacervates at equimolar (1:1) mole ratios of DTAB and SDS. The phase-transition behavior of both systems was studied over a wide range of surfactant and HFIP concentrations at the stoichiometric (1:1) mole ratio of cationic/anionic surfactants. The chemical compositions of each of the two phases (aqueous-rich and coacervate phases) were studied with regard to the concentrations of HFIP, water, and individual surfactants. It is revealed that the surfactant-rich phase (coacervate phase) contains a large percentage of fluoroalcohol relative to the aqueous phase and is enriched in both surfactants but contains a small percentage of water. Surprisingly, the concentration of water in the coacervate phase increases as the total HFIP concentration is increased while the concentration of HFIP in the coacervate phase remains relatively constant, which means a larger amount of water associated with HFIP molecules is extracted into the coacervate phase, which results in the growth of the phase. The volume of the coacervate phase increases with an increase in surfactant concentration and total HFIP %. The coacervate phase is highly enriched in the two amphiphilic ions (DTA(+) and DS

  14. Crystalline structures and mesomorphic properties of gemini diammonium surfactants with a pendant hydroxyl group.

    Science.gov (United States)

    Wei, Zengbin; Wei, Xilian; Sun, Dezhi; Liu, Jiuqiang; Tang, Xiaojuan

    2011-02-15

    A series of homologous crystals of gemini diammonium surfactants (GDAS) containing one hydroxyl substituted methylene spacer are prepared. The crystal structures of these compounds, namely [C(n)H(2)(n)(+1)-N(+) (CH(3))(2)-CH(2)CH(OH)CH(2)-N(+)(CH(3))(2)-C(n)H(2)(n)(+1)], are determined by single-crystal X-ray diffraction techniques, in order to have a better understanding of the structure relation between the solid and the mesophase. The hydroxyl groups enhance the hydrogen bonding interaction between neighboring compounds, and therefore the packing of GDAS in the solid state is arranged to form a herringbone-like mode. To the best of our knowledge, this is the first GDAS crystal with a herringbone-like structure. Their mesomorphic properties are investigated by differential scanning calorimetry, polarizing optical microscopy, X-ray powder diffraction, and rheological measurement. These compounds have relatively low melting points and form thermotropic mesophases over a broad temperature range, as compared to those without a hydroxyl substituted at the spacer. The rheological behavior of the smectic phases clearly reveals that hydrogen bonds exert a significant effect on the high values of moduli and viscosity. Moreover, the melting point and rheological parameters increase, conforming to the length of alkyl chains.

  15. Investigation of adsorption of surfactant at the air-water interface with quantum chemistry method

    Institute of Scientific and Technical Information of China (English)

    CHEN MeiLing; WANG ZhengWu; WANG HaiJun; ZHANG GeXin; TAO FuMing

    2007-01-01

    Density functional theory (DFT) of quantum chemistry was used to optimize the configuration of the anionic surfactant complexes CH3(CH2)7OSO-3(H2O)n (n=0-6) and calculate their molecular frequencies at the B3LYP/6-311+G* level. The interaction of CH3(CH2)7OSO-3 with 1 to 6 water molecules was investigated at the air-water interface with DFT. The results revealed that the hydration shell was formed in the form of H-bond between the hydrophilic group of CH3(CH2)7OSO-3 and 6 waters. The strength of H-bonds belongs to medium. Binding free energy revealed that the hydration shell was stable. The increase of the number of water molecules will cause increases of the total charge of hydrophilic group and S10-O9-C8 bond angle, but decreases of the alkyl chain length and the bond lengths of S10-O11,S10-O12 as well as S10-O13, respectively.

  16. Bile acid-surfactant interactions at the liquid crystal/aqueous interface.

    Science.gov (United States)

    He, Sihui; Liang, Wenlang; Cheng, Kung-Lung; Fang, Jiyu; Wu, Shin-Tson

    2014-07-14

    The interaction between bile acids and surfactants at interfaces plays an important role in fat digestion. In this paper, we study the competitive adsorption of cholic acid (CA) at the sodium dodecyl sulfate (SDS)-laden liquid crystal (LC)/aqueous interface formed with cyanobiphenyl (nCB, n = 5-8) and the mixture of 5CB with 4-(4-pentylcyclohexyl)benzonitrile (5PCH). We find that the critical concentration of CA required to displace SDS from the interface linearly decreases from 160 μM to 16 μM by reducing the alkyl chain length of nCB from n = 8 to n = 5 and from 16 μM to 1.5 μM by increasing the 5PCH concentration from 0 wt% to 19 wt% in the 5PCH-5CB binary mixture. Our results clearly demonstrate that the sensitivity of 5PCH-5CB mixtures for monitoring the interaction between CA and SDS at the LC/aqueous interface can be increased by one order of magnitude, compared to 5CB.

  17. Adsorption of Amino Acids and Glutamic Acid-Based Surfactants on Imogolite Clays.

    Science.gov (United States)

    Bonini, Massimo; Gabbani, Alessio; Del Buffa, Stefano; Ridi, Francesca; Baglioni, Piero; Bordes, Romain; Holmberg, Krister

    2017-03-07

    Aluminum oxide surfaces are of utmost interest in different biotech applications, in particular for their use as adjuvants (i.e., booster of the immune response against infectious agents in vaccines production). In this framework, imogolite clays combine the chemical flexibility of an exposed alumina surface with 1D nanostructure. This work reports on the interaction between amino acids and imogolite, using turbidimetry, ζ-potential measurements, and Fourier transform infrared spectroscopy as main characterization tools. Amino acids with different side chain functional groups were investigated, showing that glutamic acid (Glu) has the strongest affinity for the imogolite surface. This was exploited to prepare a composite material made of a synthetic surfactant bearing a Glu polar head and a hydrophobic C12 alkyl tail, adsorbed onto the surface of imogolite. The adsorption of a model drug (rhodamine B isothiocyanate) by the hybrid was evaluated both in water and in physiological saline conditions. The findings of this paper suggest that the combination between the glutamate headgroup and imogolite represents a promising platform for the fabrication of hybrid nanostructures with tailored functionalities.

  18. Biocompatible fluorinated polyglycerols for droplet microfluidics as an alternative to PEG-based copolymer surfactants.

    Science.gov (United States)

    Wagner, Olaf; Thiele, Julian; Weinhart, Marie; Mazutis, Linas; Weitz, David A; Huck, Wilhelm T S; Haag, Rainer

    2016-01-07

    In droplet-based microfluidics, non-ionic, high-molecular weight surfactants are required to stabilize droplet interfaces. One of the most common structures that imparts stability as well as biocompatibility to water-in-oil droplets is a triblock copolymer surfactant composed of perfluoropolyether (PFPE) and polyethylene glycol (PEG) blocks. However, the fast growing applications of microdroplets in biology would benefit from a larger choice of specialized surfactants. PEG as a hydrophilic moiety, however, is a very limited tool in surfactant modification as one can only vary the molecular weight and chain-end functionalization. In contrast, linear polyglycerol offers further side-chain functionalization to create custom-tailored, biocompatible droplet interfaces. Herein, we describe the synthesis and characterization of polyglycerol-based triblock surfactants with tailored side-chain composition, and exemplify their application in cell encapsulation and in vitro gene expression studies in droplet-based microfluidics.

  19. Guanidinium ionic liquid-based surfactants as low cytotoxic extractants: Analytical performance in an in-situ dispersive liquid-liquid microextraction method for determining personal care products.

    Science.gov (United States)

    Pacheco-Fernández, Idaira; Pino, Verónica; Ayala, Juan H; Afonso, Ana M

    2017-05-01

    The IL-based surfactant octylguanidinium chloride (C8Gu-Cl) was designed and synthetized with the purpose of obtaining a less harmful surfactant: containing guanidinium as core cation and a relatively short alkyl chain. Its interfacial and aggregation behavior was evaluated through conductivity and fluorescence measurements, presenting a critical micelle concentration value of 42.5 and 44.6mmolL(-1), respectively. Cytotoxicity studies were carried out with C8Gu-Cl and other IL-based and conventional surfactants, specifically the analogue 1-octyl-3-methylimidazolium chloride (C8MIm-Cl), and other imidazolium- (C16MIm-Br) and pyridinium- (C16Py-Cl) based surfactants, together with the conventional cationic CTAB and the conventional anionic SDS. From these studies, C8Gu-Cl was the only one to achieve the classification of low cytotoxicity. An in situ dispersive liquid-liquid microextraction (DLLME) method based on transforming the water-soluble C8Gu-Cl IL-based surfactant into a water-insoluble IL microdroplet via a simple metathesis reaction was then selected as the extraction/preconcentration method for a group of 6 personal care products (PCPs) present in cosmetic samples. The method was carried out in combination with high-performance liquid chromatography (HPLC) and diode array detection (DAD). The method was properly optimized, requiring the use of only 30μL of C8Gu-Cl for 10mL of aqueous sample with a NaCl content of 8% (w/v) to adjust the ionic strength and pH value of 5. The metathesis reaction required the addition of the anion exchange reagent (bis[(trifluoromethyl)sulfonyl]imide - 1:1 molar ratio), followed by vortex and centrifugation, and dilution of the final microdroplet up to 60μL with acetonitrile before the injection in the HPLC-DAD system. The optimum in situ DLLME-HPLC-DAD method takes ∼10min for the extraction step and ∼22min for the chromatographic separation, with analytical features of low detection limits: down to 0.4μgL(-1); high

  20. Effect of polyester blends in hydroentangled raw and bleached cotton nonwoven fabrics on the adsorption of alkyl-dimethyl-benzyl-ammonium chloride

    Science.gov (United States)

    The adsorption kinetics and isotherms of alkyl-dimethyl-benzyl-ammonium chloride (ADBAC), a cationic surfactant commonly employed as an antimicrobial agent, on hydroentangled nonwoven fabrics (applicable for wipes) including raw cotton, bleached cotton, and their blends with polyester (PES) were stu...

  1. Self-consistent field modeling of non-ionic surfactants at the silica-water interface: Incorporating molecular detail

    NARCIS (Netherlands)

    Postmus, B.R.; Leermakers, F.A.M.; Cohen Stuart, M.A.

    2008-01-01

    We have constructed a model to predict the properties of non-ionic (alkyl-ethylene oxide) (C(n)E(m)) surfactants, both in aqueous solutions and near a silica surface, based upon the self-consistent field theory using the Scheutjens-Fleer discretisation scheme. The system has the pH and the ionic

  2. Terrestrial risk assessment for linear alkyl benzene sulfonate (LAS) in sludge-amended soils.

    Science.gov (United States)

    de Wolf, W; Feijtel, T

    1998-03-01

    A comparison of the estimated environmental concentration and the effect concentrations (in the laboratory or field) in the receiving compartment form the basis of environmental risk assessments. This paper reviews processes that critically influence the fate of LAS in the terrestrial environment. Concentrations of LAS in sludge are quite high due to sorption to primary sludge, precipitation of Ca and Mg-salts of LAS, and lack of biodegradation under anaerobic digestion. This implies that when sludge is applied to soil e.g. as a fertilizer, considerable amounts of this important surfactant may enter the terrestrial environment. Influence of aerobic situations on LAS concentrations during sludge storage needs further research to allow incorporation into the risk assessment. Aerobic biodegradation in soil is considered the most important removal mechanism of LAS loading to the terrestrial environment through sludge-amendment. Sorption plays a role in determining the residence time of a chemical in the soil, hereby enabling more time for biodegradation to occur. In addition, sorption may affect the expression of effects of surfactants towards benthic and soil dwelling organisms and plants. Another factor that needs further attention is the form of LAS in the environment, which is not similar to the commercial material applied in detergents. The differential sorption and biodegradation of the LAS components lead to a shift in the alkyl chain length (homologue), and phenylisomer distribution towards increased hydrophobicity. Also, occurrence of Ca/Mg-salts in the environment versus the Na-salt for the commercial material critically impacts the extrapolation of effects data obtained in lab studies (mostly performed with the commercial material) to the field. The literature data were used in combination with strategies and methods provided by the European Union Technical Guidance Document in support of risk assessment of new and notified substances (1996) for the

  3. Surfactant-Amino Acid and Surfactant-Surfactant Interactions in Aqueous Medium: a Review.

    Science.gov (United States)

    Malik, Nisar Ahmad

    2015-08-01

    An overview of surfactant-amino acid interactions mainly in aqueous medium has been discussed. Main emphasis has been on the solution thermodynamics and solute-solvent interactions. Almost all available data on the topic has been presented in a lucid and simple way. Conventional surfactants have been discussed as amphiphiles forming micelles and amino acids as additives and their effect on the various physicochemical properties of these conventional surfactants. Surfactant-surfactant interactions in aqueous medium, various mixed surfactant models, are also highlighted to assess their interactions in aqueous medium. Finally, their applied part has been taken into consideration to interpret their possible uses.

  4. Surface tension method for determining binding constants for cyclodextrin inclusion complexes of ionic surfactants

    Energy Technology Data Exchange (ETDEWEB)

    Dharmawardana, U.R.; Christian, S.D.; Tucker, E.E.; Taylor, R.W.; Scamehorn, J.F. (Univ. of Oklahoma, Norman, OK (United States))

    1993-09-01

    A new method has been developed for determining binding constants of complexes of cyclodextrins with surface-active compounds, including water-soluble ionic surfactants. The technique requires measuring the change in surface tension caused by addition of a cyclodextrin (CD) to aqueous solutions of the surfactant; the experimental results lead directly to inferred values of the thermodynamic activity of the surfactant. Surface tension results are reported for three different surfactants sodium dodecyl sulfate (SDS), cetylpyridinium chloride (CPC), and cetyltrimethylammonium bromide (CTAB) in the presence and in the absence of added [beta]-CD. Data for CPC have been obtained at surfactant concentrations below and above the critical micelle concentration. Correlations between surface tension and surfactant activity are expressed by the Szyszkowski equation, which subsumes the Langmuir adsorption model and the Gibbs equation. It is observed that the surface tension increases monotonically as [beta]-cyclodextrin is added to ionic surfactant solutions. At concentrations of CD well in excess of the surfactant concentration, the surface tension approaches that of pure water, indicating that neither the surfactant-CD complexes nor CD itself are surface active. Binding constants are inferred from a model that incorporates the parameters of the Szyszkowski equation and mass action constants relating to the formation of micelles from monomers of the surfactant and the counterion. Evidence is given that two molecules of CD can complex the C-16 hydrocarbon chain of the cetyl surfactants. 30 refs., 5 figs., 1 tab.

  5. Preparation and evaluation of sulphonamide nonionic surfactants

    Directory of Open Access Journals (Sweden)

    Ahmed, M. H. M.

    2010-03-01

    Full Text Available Alkyl (octyl, decyl and dodecyl; C8,C10 and C12 benzene sulphonyl chloride was used in the preparation of a novel series of nonionic surfactants (IV-VIa-c, (VII-IX a-c and (X-XIIa-c. The preparations were completed by reacting each alkyl (C8,C10 and C12 benzene sulphonyl chloride with ethanolamine to give (I-III respectively. The resulting products were reacted separately with ethylene oxide in the presence of different (base KOH, Lewis acid SnCl4 and k10 clay catalysts to produce different moles of nonionic surfactants (5, 7 and 9 in sequence corresponding to (IV-VIa-c, (VII-IX a-c and (X-XIIa-c respectively. The chemical structures of prepared nonionic surfactants were elucidated by IR and 1HNMR spectra. The surface activity, biodegradability and biological activities of the prepared compounds were investigated. The obtained data show that these compounds have good surface and biological activities as well as reasonable biodegradability properties.Cloruros de sulfonilbenceno alquilados (octil, decil, dodecil; C8, C10 y C12 fueron usados en la preparación de una nueva serie de surfactantes no iónicos (IV-VIa-c, (VII-IX a-c and (X-XIIa-c. Las preparaciones fueron completadas por reacción de cada cloruro de sulfonilbenceno alquilado (C8, C10 y C12 con etanolamina para dar los compuestos (IIII, respectivamente. Los anteriores productos reaccionaron separadamente con óxido de etileno en presencia de diferentes catalizadores (la base KOH, el ácido de Lewis SnCl4 y la arcilla k10 para producir secuencialmente diferentes surfactantes no iónicos con distintos moles de óxido de etileno (5, 7 y 9: (IV-VIa-c, (VII-IXa-c and (X-XIIa-c, respectivamente. La estructura química de los surfactantes no iónicos preparados fueron elucidadas mediante sus espectros de IR y 1H RMN. Las propiedades tensoactivas, biodegradabilidad y actividad biológica de los compuestos preparados fueron investigados. Los datos obtenidos muestran que estos compuestos tienen

  6. Levels and pattern of alkyl nitrates, multifunctional alkyl nitrates, and halocarbons in the air over the Atlantic Ocean

    Science.gov (United States)

    Fischer, Ralf G.; Kastler, Jürgen; Ballschmiter, Karlheinz

    2000-06-01

    The Albatross Campaign was a research cruise of the German research vessel RV Polarstern (cruise ANT XFV/1) in October and November 1996 across the Atlantic Ocean. The cruise started in Bremerhaven, Germany, reached the polar region at 67°N, followed the 30°W meridian longitude, crossed the equatorial region, and ended at 50°S at Punta Quilla, Argentina. A second cruise leg closer to the African continent started from Capetown, South Africa, passed the Canary Island, and ended through the English Channel at Bremerhaven, Germany, in May/June 1998. Measurements of atmospheric levels of C1-C13 alkyl mononitrates, 24 alkyl dinitrates (C3-C6), 19 hydroxy alkyl nitrates (C2-C6), and benzyl nitrate, as well as the halocarbons tetrachloroethene, hexachloroethane, and bromoform are presented in this work. The halocarbons are used to assess the origin of the air parcels analyzed. Levels and patterns of multifunctional alkyl nitrates in the marine air are described here for the first time. The air masses include polluted air from the northern Europe, as well as highly degraded air masses of the South Atlantic trade wind region that represent global baseline levels. Two independent analytical methods were used in combination to cover the whole range of organic nitrates. First, the low-volume adsorptive enrichment of organic traces on Tenax, followed by thermodesorption cold trap HRGC-ECD and thermodesorption cold trap HRGC-(EI)MSD was used. Second, high-volume adsorptive enrichment of organic traces on silica gel was applied followed by solvent desorption, NP-HPLC group separation, and HRGC-(EI)-MSD. Short-chain alkyl nitrates (C4-C6) showed mixing ratios in the range of 0.2-2.5 parts per trillion by volume (pptv), with a local minimum for the tropical regions and significantly lower ratios for the Southern Hemisphere. The mixing ratio of the sum of 36 long-chain alkyl mononitrates (C7-C13) ranged from 0.02-0.43 pptv, the mixing ratio of the sum of 23 alkyl dinitrates (C3-C

  7. Molecular simulation of alkyl monolayers on the Si(111)surface

    Institute of Scientific and Technical Information of China (English)

    YUAN; Shiling; (苑世领); CAI; Zhengting; (蔡政亭); XIAO; Li; (肖莉); XU; Guiying; (徐桂英); LIU; Yongjun; (刘永军)

    2003-01-01

    The structure of twelve-carbon monolayers on the H-terminated Si(111) surface is investigated by molecular simulation method. The best substitution percent on Si(111) surface obtained via molecular mechanics calculation is equal to 50%, and the (8×8) simulated cell can be used to depict the structure of alkyl monolayer on Si surface. After two-dimensional cell containing alkyl chains and four-layer Si(111) crystal at the substitution 50% is constructed, the densely packed and well-ordered monolayer on Si(111) surface can be shown through energy minimization in the suitable-size simulation cell. These simulation results are in good agreement with the experiments. These conclusions show that molecular simulation can provide otherwise inaccessible mesoscopic information at the molecular level, and can be considered as an adjunct to experiments.

  8. Tunable Oleo-Furan Surfactants by Acylation of Renewable Furans

    Energy Technology Data Exchange (ETDEWEB)

    Park, Dae Sung; Joseph, Kristeen E.; Koehle, Maura; Krumm, Christoph; Ren, Limin; Damen, Jonathan N.; Shete, Meera H.; Lee, Han Seung; Zuo, Xiaobing; Lee, Byeongdu; Fan, Wei; Vlachos, Dionisios G.; Lobo, Raul F.; Tsapatsis, Michael; Dauenhauer, Paul J.

    2016-11-23

    An important advance in fluid surface control was the amphiphilic surfactant comprised of coupled molecular structures (i.e. hydrophilic and hydrophobic) to reduce surface tension between two distinct fluid phases. However, implementation of simple surfactants has been hindered by the broad range of applications in water containing alkaline earth metals (i.e. hard water), which disrupt surfactant function and require extensive use of undesirable and expensive chelating additives. Here we show that sugar-derived furans can be linked with triglyceride-derived fatty acid chains via Friedel-Crafts acylation within single layer (SPP) zeolite catalysts. These alkylfuran surfactants independently suppress the effects of hard water while simultaneously permitting broad tunability of size, structure, and function, which can be optimized for superior capability for forming micelles and solubilizing in water.

  9. Derivation of original RESP atomic partial charges for MD simulations of the LDAO surfactant with AMBER: applications to a model of micelle and a fragment of the lipid kinase PI4KA.

    Science.gov (United States)

    Karakas, Esra; Taveneau, Cyntia; Bressanelli, Stéphane; Marchi, Massimo; Robert, Bruno; Abel, Stéphane

    2017-01-01

    In this paper, we describe the derivation and the validation of original RESP atomic partial charges for the N, N-dimethyl-dodecylamine oxide (LDAO) surfactant. These charges, designed to be fully compatible with all the AMBER force fields, are at first tested against molecular dynamics simulations of pure LDAO micelles and with a fragment of the lipid kinase PIK4A (DI) modeled with the QUARK molecular modeling server. To model the micelle, we used two distinct AMBER force fields (i.e. Amber99SB and Lipid14) and a variety of starting conditions. We find that the micelle structural properties (such as the shape, size, the LDAO headgroup hydration, and alkyl chain conformation) slightly depend on the force field but not on the starting conditions and more importantly are in good agreement with experiments and previous simulations. We also show that the Lipid14 force field should be used instead of the Amber99SB one to better reproduce the C(sp3)C(sp3)C(sp3)C(sp3) conformation in the surfactant alkyl chain. Concerning the simulations with LDAO-DI protein, we carried out different runs at two NaCl concentrations (i.e. 0 and 300 mM) to mimic, in the latter case, the experimental conditions. We notice a small dependence of the simulation results with the LDAO parameters and the salt concentration. However, we find that in the simulations, three out of four tryptophans of the DI protein are not accessible to water in agreement with our fluorescence spectroscopy experiments reported in the paper.

  10. Methods of making alkyl esters

    Science.gov (United States)

    Elliott, Brian

    2010-08-03

    A method comprising contacting an alcohol, a feed comprising one or more glycerides and equal to or greater than 2 wt % of one or more free fatty acids, and a solid acid catalyst, a nanostructured polymer catalyst, or a sulfated zirconia catalyst in one or more reactors, and recovering from the one or more reactors an effluent comprising equal to or greater than about 75 wt % alkyl ester and equal to or less than about 5 wt % glyceride.

  11. Structure and Conformational Dynamics of DMPC/Dicationic Surfactant and DMPC/Dicationic Surfactant/DNA Systems

    Directory of Open Access Journals (Sweden)

    Maciej Kozak

    2013-04-01

    Full Text Available Amphiphilic dicationic surfactants, known as gemini surfactants, are currently studied for gene delivery purposes. The gemini surfactant molecule is composed of two hydrophilic “head” groups attached to hydrophobic chains and connected via molecular linker between them. The influence of different concentrations of 1,5-bis (1-imidazolilo-3-decyloxymethyl pentane chloride (gemini surfactant on the thermotropic phase behaviour of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC bilayers with and without the presence of DNA was investigated using Fourier transformed infrared (FTIR and circular dichroism (CD spectroscopies, small angle scattering of synchrotron radiation and differential scanning calorimetry. With increasing concentration of surfactant in DMPC/DNA systems, a disappearance of pretransition and a decrease in the main phase transition enthalpy and temperature were observed. The increasing intensity of diffraction peaks as a function of surfactant concentration also clearly shows the ability of the surfactant to promote the organisation of lipid bilayers in the multilayer lamellar phase.

  12. Synthesis, characterization and coordination properties of bis(alkyl)selenosalen ligands.

    Science.gov (United States)

    Panda, Snigdha; Krishna, G Rama; Reddy, C Malla; Zade, Sanjio S

    2011-07-07

    New bis (alkyl) selenosalen podand ligands having Se2N2 donor sites have been synthesized by the condensation of unsymmetrical o-formylphenyl alkyl selenide (1-3) with ethylenediamine. The reaction of bis(alkyl)selenosalen podands with Pd(II) and Pt(II) afforded selenoether-selenolate coordination complexes 7-10via cleavage of one of the two Se-C(alkyl) bonds of bis(alkyl)selenosalen podands upon complexation. DFT calculations revealed that the cleavage of Se-C(alkyl) bonds occurred possibly via S(N)2 mechanism instead of a sequence of oxidative addition and reductive elimination reactions. The spectral data and elemental analyses confirmed the formation of selenoether-selenolate complexes. The structures of the podands N,N'-bis[(2-methylseleno)phenylmethylene]-1,2-ethanediamine (4), N,N'-bis[(2-decylseleno)phenylmethylene]-1,2-ethanediamine (5) and the selenoether-selenolate complex 8 have been determined by single crystal X-ray diffraction analysis. The crystal structure of 5 showed SeH interaction with a ladder like 3D supramolecular arrangement via interdigitation of long alkyl chains. Comparison of crystal packing of podands 4 and 5 indicates that the alkyl chain length has significant impact on the crystal packing. The platinum selenolate complex 8 shows a square planar arrangement around the Pt centre, where the Se atoms in the selenolate and the selenoether have nearly equal Pt-Se bond length. This journal is © The Royal Society of Chemistry 2011

  13. Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water

    OpenAIRE

    2007-01-01

    Low-cost adsorbents were tested to remove anionic surfactants from laundry rinsing water to allow re-use of water. Adsorbents were selected corresponding to the different surfactant adsorption mechanisms. Equilibrium adsorption studies of linear alkyl benzene sulfonate (LAS) show that ionic interaction results in a high maximum adsorption capacity on positively charged adsorbents of 0.6–1.7 g LAS/g. Non-ionic interactions, such as hydrophobic interactions of LAS with non-ionic resins or activ...

  14. Optimization of Surfactant Mixtures and Their Interfacial Behavior for Advanced Oil Recovery

    Energy Technology Data Exchange (ETDEWEB)

    Somasundaran, Prof. P.

    2002-03-04

    The objective of this project was to develop a knowledge base that is helpful for the design of improved processes for mobilizing and producing oil left untapped using conventional techniques. The main goal was to develop and evaluate mixtures of new or modified surfactants for improved oil recovery. In this regard, interfacial properties of novel biodegradable n-alkyl pyrrolidones and sugar-based surfactants have been studied systematically. Emphasis was on designing cost-effective processes compatible with existing conditions and operations in addition to ensuring minimal reagent loss.

  15. Tuning of protein-surfactant interaction to modify the resultant structure.

    Science.gov (United States)

    Mehan, Sumit; Aswal, Vinod K; Kohlbrecher, Joachim

    2015-09-01

    Small-angle neutron scattering and dynamic light scattering studies have been carried out to examine the interaction of bovine serum albumin (BSA) protein with different surfactants under varying solution conditions. We show that the interaction of anionic BSA protein (pH7) with surfactant and the resultant structure are strongly modified by the charge head group of the surfactant, ionic strength of the solution, and mixed surfactants. The protein-surfactant interaction is maximum when two components are oppositely charged, followed by components being similarly charged through the site-specific binding, and no interaction in the case of a nonionic surfactant. This interaction of protein with ionic surfactants is characterized by the fractal structure representing a bead-necklace structure of micellelike clusters adsorbed along the unfolded protein chain. The interaction is enhanced with ionic strength only in the case of site-specific binding of an anionic surfactant with an anionic protein, whereas it is almost unchanged for other complexes of cationic and nonionic surfactants with anionic proteins. Interestingly, the interaction of BSA protein with ionic surfactants is significantly suppressed in the presence of nonionic surfactant. These results with mixed surfactants thus can be used to fold back the unfolded protein as well as to prevent surfactant-induced protein unfolding. For different solution conditions, the results are interpreted in terms of a change in fractal dimension, the overall size of the protein-surfactant complex, and the number of micelles attached to the protein. The interplay of electrostatic and hydrophobic interactions is found to govern the resultant structure of complexes.

  16. Sizing up surfactant synthesis.

    Science.gov (United States)

    Han, SeungHye; Mallampalli, Rama K

    2014-08-01

    Phosphatidylcholine is generated through de novo synthesis and remodeling involving a lysophospholipid. In this issue of Cell Metabolism, research from the Shimizu lab (Harayama et al., 2014) demonstrates the highly selective enzymatic behavior of lysophospholipid acyltransferases. The authors present an enzymatic model for phosphatidylcholine molecular species diversification that impacts surfactant formation.

  17. Vesicle formation and stability in the surfactant sodium 4-(1'-heptylnonyl) benzenesulfonate

    Energy Technology Data Exchange (ETDEWEB)

    Franses, E.I.; Talmon, Y.; Scriven, L.E.; Davis, H.T.; Miller, W.G.

    1982-04-01

    Surfactants composed of a hydrophilic moiety covalently attached to the end of a hydrocarbon chain (e.g., sodium dodecyl sulfate), spontaneously form micelles, equilibrium aggregates, in solution if the surfactant concentration exceeds a critical value called the CMC. Naturally occurring double-tail surfactants (e.g., phospholipids) are not known to form micelles. Over a considerable range in surfactant concentration, 2 phases coexist in equilibrium: a hydrated, multilamellar (smectic) surfactant phase and an aqueous phase saturated with surfactant. In this report the preparation of vesicles, their direct, unstained visualization by electron microscopy, and investigation of their stability and structure by turbidimetry, conductimetry, light microscopy, densitometry, scanning calorimetry, and nuclear magnetic resonance spectroscopy are discussed. Dispersed liquid crystal was studied by the same means. For comparison, parallel studies on bovine lecithin are presented. From the results, it is concluded that these vesicles may be stable for many months, but eventually revert to multilamellar liquid crystals.

  18. Solution behaviour of new cationic surfactants derived from Guerbet alcohols and their use in hair conditioners.

    Science.gov (United States)

    Yahagi, K; Hoshino, N; Hirota, H

    1991-10-01

    Summary The solution behaviour of new cationic surfactants, synthesized by using long-chain Guerbet alcohols, in water was investigated by a polarizing microscopic technique, differential scanning calorimetry, and electric conductivity measurements. These surfactants show the gel-liquid crystalline phase transition to be lower than 0 degrees C and form lamellar liquid crystals even in cold water and at low concentrations of surfactants. The sorption of cationic surfactants from aqueous solutions onto hair was determined as a function of temperature. The effect of adsorbed cationic surfactants on the critical surface tension and kinetic frictional coefficients of hair surface have been investigated. These surface characteristics of hair treated with quaternary ammonium compounds derived from Guerbet alcohols were found to be significantly improved. These results can be explained by the high ability of sorption onto hair. Hair rinses and conditioners having excellent ease of combing or brushing for wet and dry hair can be formulated by the application of these cationic surfactants.

  19. Determination of alkylbenzenesulfonate surfactants in groundwater using macroreticular resins and carbon-13 nuclear magnetic resonance spectrometry

    Science.gov (United States)

    Thurman, E.M.; Willoughby, T.; Barber, L.B.; Thorn, K.A.

    1987-01-01

    Alkylbenzenesulfonate surfactants were determined in groundwater at concentrations as low as 0.3 mg/L. The method uses XAD-8 resin for concentration, followed by elution with methanol, separation of anionic and nonionic surfactants by anion exchange, quantitation by titration, and identification by 13C nuclear magnetic resonance spectrometry. Laboratory standards and field samples containing straight-chain and branched-chain alkylbenzenesulfonates, sodium dodecyl sulfate, and alkylbenzene ethoxylates were studied. The XAD-8 extraction of surfactants from groundwater was completed in the field, which simplified sample preservation and reduced the cost of transporting samples.

  20. Small angle neutron scattering studies on the interaction of cationic surfactants with bovine serum albumin

    Indian Academy of Sciences (India)

    Nuzhat Gull; S Chodankar; V K Aswal; Kabir-Ud-Din

    2008-11-01

    The structure of the protein–surfactant complex of bovine serum albumin (BSA) and cationic surfactants has been studied by small angle neutron scattering. At low concentrations, the CTAB monomers are observed to bind to the protein leading to an increase in its size. On the other hand at high concentrations, surfactant molecules aggregate along the unfolded polypeptide chain of the protein resulting in the formation of a fractal structure representing a necklace model of micelle-like clusters randomly distributed along the polypeptide chain. The fractal dimension as well as the size and number of micelles attached to the complex have been determined.

  1. Silver-catalyzed cross-coupling reactions of alkyl bromides with alkyl or aryl Grignard reagents

    OpenAIRE

    Someya, Hidenori; Yorimitsu, Hideki; Oshima, Koichiro

    2009-01-01

    reatment of secondary or tertiary alkyl bromides with alkyl Grignard reagents in the presence of catalytic amounts of silver bromide and potassium fluoride in CH2Cl2 afforded the corresponding cross-coupling products in reasonable yields. Moreover, silver showed catalytic activity for the cross-coupling reactions of alkyl bromides with aryl Grignard reagents.

  2. 40 CFR 721.1875 - Boric acid, alkyl and substituted alkyl esters (generic name).

    Science.gov (United States)

    2010-07-01

    ... alkyl esters (generic name). 721.1875 Section 721.1875 Protection of Environment ENVIRONMENTAL... esters (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance boric acid, alkyl and substituted alkyl esters (PMN P-86-1252) is subject to reporting...

  3. Optimization of layered double hydroxide stability and adsorption capacity for anionic surfactants

    OpenAIRE

    2007-01-01

    Low cost adsorption technology offers high potential to clean up laundry rinsing water. From an earlier selection of adsorbents, layered double hydroxide (LDH) proved to be an interesting material for the removal of anionic surfactant, linear alkyl benzene sulfonate (LAS) which is the main contaminant in rinsing water. The main research question was to identify the effect of process parameters of the LDH synthesis on the stability of the LDH structure and the adsorption capacity of LAS. LDH w...

  4. alkylation of toluene over basic catalysts - key requirements for side chain alkylation

    NARCIS (Netherlands)

    Palomares gimeno, A.E.; Palomares, A.E.; Eder-Mirth, G.; Mirth, G.C.; Rep, M.; Rep, M.; Lercher, J.A.

    1998-01-01

    In situinfrared spectroscopy was used to study sorption and reaction of toluene and methanol over various basic catalysts (MgO, hydrotalcites, and basic zeolites). The size of the metal cations controls the preference of sorbing methanol or toluene; i.e., the larger the metal cation, the higher the

  5. Evaluation of the influence of base and alkyl bromide on synthesis of pyrazinoic acid esters through fatorial design

    Directory of Open Access Journals (Sweden)

    João Paulo dos Santos Fernandes

    2009-01-01

    Full Text Available Pyrazinoic acid esters have been synthesized as prodrugs of pyrazinoic acid. In the literature, its preparation is reported through the reaction of pyrazinoyl chloride with alcohols and the reaction with DCC/DMAP. In this work, it is reported a 2² factorial design to evaluate the preparation of these esters through the substitution of alkyl bromides with carboxylate anion. The controlled factors were alkyl chain length of bromides (ethyl and hexyl and the used base (triethylamine and DBU. Results revealed that the used base used has significant effect on yield, and alkyl bromide used has neither significant influence, nor its interaction effect with base.

  6. Mimicking cell membrane-like structures on alkylated silicon surfaces by peptide amphiphiles

    Energy Technology Data Exchange (ETDEWEB)

    Shamsi, Fahimeh, E-mail: neyayesh8@yahoo.com [Biophysics and Bioengineering, School of Chemical and Biomolecular Engineering, University of Sydney, Sydney, NSW 2006 (Australia); Coster, Hans G.L. [Biophysics and Bioengineering, School of Chemical and Biomolecular Engineering, University of Sydney, Sydney, NSW 2006 (Australia)

    2011-11-01

    Highlights: {yields} Lipidated peptide amphiphiles were hydrophobically attached onto an alkylated surface. {yields} Morphology of nanofibres of the peptide amphiles depended on the acyl chain length. {yields} We show that extended 2D analogues of the nanofibre surface can be constructed. {yields} Peptide amphiphiles with shorter acyl chains formed more homogeneous layers. - Abstract: We present a new strategy for flexible attachment of peptide amphiphiles on functionalized silicon surfaces. This method involves the production of an alkylated surface on which a lipidated peptide can then be attached through hydrophobic interaction. We applied this to two derivatives of amphiphilic peptide molecules with the same amino acid sequence (A-A-A-A-G-G-G-E-R-G-D) but different in alkyl chain lengths (palmitic acid, undecanoic acid). The basis of this work was to develop substrates which are more biocompatible and bioactive. The ultra-thin peptide amphiphile films were characterized using electrical impedance spectroscopy (EIS), X-ray photoelectron spectroscopy (XPS) and Fourier transform infrared (ATR-FTIR) spectroscopy. The results demonstrated that the length of the alkyl chain in the peptide amphiphile affects the packing and coverage of the peptides on the silicon surface.

  7. Influence of the hydrophilic head size and hydrophobic tail length of surfactants on the ability of micelles to stabilize citral.

    Science.gov (United States)

    Hong, Chi Rac; Park, Sung Joon; Choi, Seung Jun

    2016-07-01

    Surfactant-made micelles can control the rate of chemical degradation of poorly water-soluble food flavors. To evaluate how the molecular structure of surfactant has an influence on the chemical decomposition rate of citral, micelles were prepared with polyoxyethylene alkyl ether-type surfactants that had similar molecular structures but various hydrophilic head sizes and hydrophobic tail lengths. At a critical 20× micelle concentration of surfactant, there was no significant difference in the chemical degradation rate of citral in micelles in neutral pH, regardless of the hydrophilic head size or hydrophobic tail length. In an acidic environment, the degradation rate constant of citral generally increased proportionally with increasing hydrophilic head size of surfactant (0.1563 and 0.2217 for surfactants with 23 and 100 oxyethylene units, respectively) but the length of hydrophobic tail did not affect the citral stability. Also, little difference (0.2217 and 0.2265 for surfactant having 100 oxyethylene units with and without Fe(3+) ) in degradation rate constant of citral between simple micellar solution and micellar solution containing iron suggested that iron ions could not accelerate citral degradation in micelles, regardless of the form of iron (Fe(2+) and Fe(3+) ). This work concludes that although the concentration of surfactant could be relevant, if its concentration could be controlled in the same manner as the critical micelle concentration, then a polyethylene alkyl ether-type surfactant with a small hydrophilic head could more efficiently stabilize citral at an acidic pH. © 2015 Society of Chemical Industry. © 2015 Society of Chemical Industry.

  8. DNA-poly(vinyl alcohol) gel matrices: release properties are strongly dependent on electrolytes and cationic surfactants.

    Science.gov (United States)

    Valente, Artur J M; Cruz, Sandra M A; Murtinho, Dina M B; Miguel, M Graça; Muniz, Edvani C

    2013-01-01

    The release of DNA from cryogel PVA-DNA gel matrices to different electrolyte aqueous solutions was investigated. The rate of release and the distribution coefficient of DNA have been quantified by using a first order kinetic law equation, developed in the frame of a partition-based model. The release of DNA from gels to 1:1 sodium and nitrate salts shows that the transport properties are dependent on the ability of anions/cations to solubilise the DNA in the aqueous phase which, with the exception of bromide, can be related to the Hofmeister series; in the presence of multivalent electrolytes, or increasing the ionic strength, the condensation of DNA inside the gel, followed by a phase separation as seen by scanning electron microscopy, induces the retention of DNA inside the polymer matrix. The DNA condensation and/or phase separation, which contribute to a decrease in the water volume fraction inside the gel, determined by swelling degree experiments, also lead to a decrease in the rate constant of DNA release; such decrease can be justified by the difficulty of the molecular aggregate to move through out the polymeric structure. The DNA release is also dependent on the pH of the bulk solution. The effect of uni- and di-valent cationic surfactants on the release properties of DNA was also evaluated. Our findings suggest that the kinetics of DNA release depends on a complex balance between different structural properties of the surfactants, namely charge, bulkiness of the headgroup and alkyl chain length.

  9. ORGANIC-INORGANIC HYBRIDS PREPARED FROM ALKYL PHOSPHONIUM SALTS INTERCALATED MONTMORILLONITES

    Directory of Open Access Journals (Sweden)

    SAHELI GANGULY

    2012-12-01

    Full Text Available Present investigation is focused on systematic and detailed characterization of alkyl phosphonium intercalated montmorillonite (MMT. The objective of the work is to provide a better understanding of the specific changes in properties of the hybrid material with changes in structure of incoming organic cations. In the present work, Na-MMT was intercalated with phosphonium salts of two different cationic head compositions namely alkyl triphenyl and alkyl tributyl groups. Length of alkyl chain was also varied. Resultant organic-inorganic hybrids were characterized by X-ray diffraction (XRD, Transmission electron microscopy (TEM, Thermogravimetry (TG and Fourier transformed infrared spectroscopy (FTIR. Effective volume occupied by the cationic heads influenced interlayer arrangements. Intercalated MMT with two different cationic heads behaved differently in relation to thermal decomposition patterns. Possible explanation was given based on hybridization of bonds. Van der Waals attachment of alkyl chains influenced the interlayer stacking and organic loading. Attempts were made to correlate the changes in properties of intercalated MMT with the structural aspects of incoming organic cations.

  10. Alkyl caffeates improve the antioxidant activity, antitumor property and oxidation stability of edible oil.

    Directory of Open Access Journals (Sweden)

    Jun Wang

    Full Text Available Caffeic acid (CA is distributed widely in nature and possesses strong antioxidant activity. However, CA has lower solubility in non-polar media, which limits its application in fat-soluble food. To increase the lipophilicity of natural antioxidant CA, a series of alkyl caffeates were synthesized and their antioxidant and antitumor activities were investigated. The antioxidant parameters, including the induction period, acid value and unsaturated fatty acid content, of the alkyl caffeates in edible oil were firstly investigated. The results indicated that alkyl caffeates had a lower DPPH IC₅₀ (14-23 µM compared to CA, dibutyl hydroxy toluene (BHT and Vitamin C (24-51 µM, and significantly inhibited four human cancer cells (SW620, SW480, SGC7901 and HepG2 with inhibition ratio of 71.4-78.0% by a MTT assay. With regard to the induction period and acid value assays, methyl and butyl caffeates had higher abilities than BHT to restrain the oxidation process and improve the stability of edible oil. The addition of ethyl caffeate to oil allowed maintenance of a higher unsaturated fatty acid methyl ester content (68.53% at high temperatures. Overall, the alkyl caffeats with short chain length (n<5 assessed better oxidative stability than those with long chain length. To date, this is the first report to the correlations among the antioxidant activity, anticancer activity and oxidative stability of alkyl caffeates.

  11. Process for the preparation of alkyl glycosides

    NARCIS (Netherlands)

    De Goede, A.T.J.; Van der Leij, I.G.; Van der Heijden, A.M.; Van Rantwijk, F.; Van Bekkum, H.

    1996-01-01

    Abstract of WO 9636640 (A2) The present invention relates to a process for the preparation of alkyl glycosides by reacting an alcohol with a saccharide or a lower-alkyl glycoside in the presence of a catalyst, wherein the catalyst is a mesoporous silica-based molecular sieve material. This proce

  12. Electronic structure and mesoscopic simulations of nonylphenol ethoxylate surfactants. a combined DFT and DPD study.

    Science.gov (United States)

    Valencia, Diego; Aburto, Jorge; García-Cruz, Isidoro

    2013-08-07

    The aim of this work was to gain insight into the effect of ethylene oxide (EO) chains on the properties of a series of nonylphenol ethoxylate (NPE) surfactants. We performed a theoretical study of NPE surfactants by means of density functional theory (DFT) and dissipative particle dynamics (DPD). Both approximations were used separately to obtain different properties. Four NPEs were selected for this purpose (EO = 4, 7, 11 and 15 length chains). DFT methods provided some electronic properties that are related to the EO units. One of them is the solvation Gibbs energy, which exhibited a linear trend with EO chain length. DPD calculations allow us to observe the dynamic behavior in water of the NPE surfactants. We propose a coarse-grained model which properly simulates the mesophases of each surfactant. This model can be used in other NPEs applications.

  13. Electronic Structure and Mesoscopic Simulations of Nonylphenol Ethoxylate Surfactants. A Combined DFT and DPD Study

    Directory of Open Access Journals (Sweden)

    Isidoro García-Cruz

    2013-08-01

    Full Text Available The aim of this work was to gain insight into the effect of ethylene oxide (EO chains on the properties of a series of nonylphenol ethoxylate (NPE surfactants. We performed a theoretical study of NPE surfactants by means of density functional theory (DFT and dissipative particle dynamics (DPD. Both approximations were used separately to obtain different properties. Four NPEs were selected for this purpose (EO = 4, 7, 11 and 15 length chains. DFT methods provided some electronic properties that are related to the EO units. One of them is the solvation Gibbs energy, which exhibited a linear trend with EO chain length. DPD calculations allow us to observe the dynamic behavior in water of the NPE surfactants. We propose a coarse-grained model which properly simulates the mesophases of each surfactant. This model can be used in other NPEs applications.

  14. MICROBIAL SURFACTANTS. I. GLYCOLIPIDS

    Directory of Open Access Journals (Sweden)

    Pirog T. Р.

    2014-02-01

    Full Text Available The review is devoted to surface-active glycolipids. The general characteristics, the physiological role of the rhamnolipids, trehalose lipids, sophorolipids, mannosylerythritol lipids and their traditional producers — the representatives of the genera Pseudozyma, Pseudomonas, Rhodococcus and Candida are given. The detailed analysis of the chemical structure, the stages of the biosynthesis and the regulation of some low molecular glycolipids are done. The own experimental data concerning the synthesis intensification, the physiological role and the practical use of Rhodococcus erythropolis IMV Ac-5017, Acinetobacter calcoaceticus IMV B-7241 and Nocardia vaccinii IMV B-7405 surfactants, which are a complex of the glyco-, phospho-, amino- and neutral lipids (glycolipids of all strains are presented by trehalose mycolates are summarized. It was found that R. erythropolis IMV Ac-5017, A. calcoaceticus IMV B-7241 and N. vaccinii IMV B-7405 surfactants have protective, antimicrobial and antiadhesive properties. It was shown that R. erythropolis IMV Ac-5017, A. calcoaceticus IMV B-7241 and N. vaccinii IMV B-7405 surfactants preparation of cultural liquid intensified the degradation of oil in water due to the activation of the natural petroleum-oxidizing microflora.

  15. MICROBIAL SURFACTANTS. II. LIPOPEPTIDES

    Directory of Open Access Journals (Sweden)

    T. P. Pirog

    2014-04-01

    Full Text Available The classification and the chemical structure of the lipopeptides and their producers (bacteria of the genera Bacillus and Pseudomonas are given. The role of the lipopeptides in cells motility, biofilm formation, metal binding and xenobiotics degradation and their action on the cells of pro- and eukaryotes is summarized. The stages of the nonribosomal lipopeptides synthesis and the role of two-component (GacA/GacS, ComA/ComP and the quorum system regulation of this process are shown. The potential of lactic acid bacteria and marine microorganisms as alternative surfactants producers (glycolipids, lipopeptides, phospholipids and fatty acids, glycolipopeptides are discussed. Their productivity and advantages over traditional producers are given as well. The properties of surfactants synthesized by lactic acid bacteria (the reduction of the surface tension, the critical micelle concentration, the stability in a wide range of pH, the temperature, the biological activity are summarized. Surfactants of nonpathogenic probiotic bacteria could be used as effective antimicrobial agents and antiadhesive and marine producers which able to synthesize unique metabolites that are not produced by other microorganisms.

  16. Electrolyte properties of 1-alkyl-2,3,5-trimethylpyrazolium cation-based room-temperature ionic liquids for lithium secondary batteries

    Energy Technology Data Exchange (ETDEWEB)

    Seki, Shiro; Kobayashi, Takeshi; Serizawa, Nobuyuki; Kobayashi, Yo; Takei, Katsuhito; Miyashiro, Hajime [Materials Science Research Laboratory, Central Research Institute of Electric Power Industry (CRIEPI), 2-11-1, Iwado-kita, Komae, Tokyo 201-8511 (Japan); Hayamizu, Kikuko; Tsuzuki, Seiji [National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Center 5, Tsukuba, Ibaraki 305-8565 (Japan); Mitsugi, Takushi; Umebayashi, Yasuhiro [Department of Chemistry, Faculty of Science, Kyushu University, Hakozaki, Higashi-ku, Fukuoka 812-8581 (Japan); Watanabe, Masayoshi [Department of Chemistry and Biotechnology, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama, Kanagawa (Japan)

    2010-09-15

    The physicochemical and electrochemical properties of three 1-alkyl-2,3,5-trimethylpyrazolium cation-based room-temperature ionic liquids with various alkyl chain lengths were investigated. The temperature dependences of density, viscosity, and ionic conductivity were obtained by precise measurements. Electrolyte properties of these room-temperature ionic liquids were also examined from the viewpoint of their uses in lithium secondary batteries ([LiCoO{sub 2} positive electrode vertical stroke electrolyte vertical stroke lithium metal negative electrode]). It was found that the alkyl chain length affects the charge-discharge performances of cells. (author)

  17. Investigation of the adsorption of anionic surfactants at different pH values by means of active carbon and the kinetics of adsorption

    OpenAIRE

    2004-01-01

    In this study, the effect of pH on the removal of anionic surfactants, such as linear alkyl benzene sulfonate (LABS) and dodecyl benzene sulfonate (DBS) by means of adsorption by activated carbon was investigated. For this purpose activated carbon was used as adsorbent. Anionic surfactant solutions with initial pH values of 3, 6, 8 and 12 were used. The adsorption isotherms for the adsorption of anionic surfactants by active carbon at different pH were determined. These adsorption isotherms w...

  18. Novel Piperazine-based Gemini and Bola Surfactants

    Institute of Scientific and Technical Information of China (English)

    Qing Shan ZHANG; Hui Miao ZHANG; Bing Nan GUO

    2006-01-01

    A series of piperazine-based Gemini and Bola surfactants were synthesized. Gemini 1and 5 have well surface activities. Their critical micelle concentrations (cmc) is 6.47×10-4 mol/L and 1.17×10-3 mol/L, respectively. Bola surfactants 2 and compound 3, possessing better water solubility, have lower surface activities. Calculation, carried out by MM2 energy minimization,showed that compound with more hydrophobic chains in a spacer of limited length is difficult to be synthesized.

  19. Comprehensive review of several surfactants in marine environments: Fate and ecotoxicity.

    Science.gov (United States)

    Jackson, Mathew; Eadsforth, Charles; Schowanek, Diederik; Delfosse, Thomas; Riddle, Andrew; Budgen, Nigel

    2016-05-01

    Surfactants are a commercially important group of chemicals widely used on a global scale. Despite high removal efficiencies during wastewater treatment, their high consumption volumes mean that a certain fraction will always enter aquatic ecosystems, with marine environments being the ultimate sites of deposition. Consequently, surfactants have been detected within marine waters and sediments. However, aquatic environmental studies have mostly focused on the freshwater environment, and marine studies are considerably underrepresented by comparison. The present review aims to provide a summary of current marine environmental fate (monitoring, biodegradation, and bioconcentration) and effects data of 5 key surfactant groups: linear alkylbenzene sulfonates, alcohol ethoxysulfates, alkyl sulfates, alcohol ethoxylates, and ditallow dimethyl ammonium chloride. Monitoring data are currently limited, especially for alcohol ethoxysulfates and alkyl sulfates. Biodegradation was shown to be considerably slower under marine conditions, whereas ecotoxicity studies suggest that marine species are approximately equally as sensitive to these surfactants as freshwater species. Marine bioconcentration studies are almost nonexistent. Current gaps within the literature are presented, thereby highlighting research areas where additional marine studies should focus.

  20. Preparation and Evaluation of Monodisperse Nonionic Surfactants Based on Fluorine-Containing Dicarbamates.

    Science.gov (United States)

    Mureau; Trabelsi; Guittard; Geribaldi

    2000-09-15

    Novel bipodal surfactants of fluorine-containing carbamate type were synthesized with satisfactory yields from the action of fluorinated diisocyanates on oligooxyethylmonomethylated ethers without solvent. The synthetic pathways via malonic intermediates were elaborated in order to use low-price commercially available compounds such as 2-F-alkylethyl iodides and oligooxyethylmonomethylated ethers as starting materials. This new class of nonionic surfactants contains one hydrophobic part and one oleophobic part, and shows peculiar properties due to the presence of two hydrophilic parts (bipodal). All these compounds are monodisperse, i.e, include a perfectly defined number of oxyethylene units. Compared with their bipodal homologues previously described within the F-alkylated series, these new structures were easily obtained from commercial raw materials and are stable against pH media. The evaluation of their behavior at the air-water interface has been studied by measurements of surface tension versus concentration. This allows us to show clearly the variation of the critical micelle concentration (cmc) from 1.1x10(-5) to 9.8x10(-3) mol.l(-1), and of the surface area per surfactant molecule versus studied structures. The dicarbamates of oligooxyethylmonomethylether of 3-(F-alkyl)propyl so realized exhibit noteworthy properties as nonionic fluorinated surfactants. Copyright 2000 Academic Press.

  1. Influence of microbial and synthetic surfactant on the biodegradation of atrazine.

    Science.gov (United States)

    Singh, Anil Kumar; Cameotra, Swaranjit Singh

    2014-02-01

    The present study reports the effect of surfactants (rhamnolipids and triton X-100) on biodegradation of atrazine herbicide by strain A6, belonging to the genus Acinetobacter. The strain A6 was able to degrade nearly 80 % of the 250-ppm atrazine after 6 days of growth. The bacterium degraded atrazine by de-alkylation process. Bacterial cell surface hydrophobicity as well as atrazine solubility increased in the presence of surfactant. However, addition of surfactant to the mineral salt media reduced the rate and extent of atrazine degradation by decreasing the bioavailability of herbicide. On the contrary, addition of surfactant to atrazine-contaminated soil increased the rate and extent of biodegradation by increasing the bioavailability of herbicide. As compared to triton X-100, rhamnolipids were more efficient in enhancing microbial degradation of atrazine as a significant amount of atrazine was removed from the soil by rhamnolipids. Surfactants added for the purpose of hastening microbial degradation may have an unintended inhibitory effect on herbicide degradation depending upon contiguous condition, thus highlighting the fact that surfactant must be judiciously used in bioremediation of herbicides.

  2. Selection and evaluation of adsorbents for the removal of anionic surfactants from laundry rinsing water.

    Science.gov (United States)

    Schouten, Natasja; van der Ham, Louis G J; Euverink, Gert-Jan W; de Haan, André B

    2007-10-01

    Low-cost adsorbents were tested to remove anionic surfactants from laundry rinsing water to allow re-use of water. Adsorbents were selected corresponding to the different surfactant adsorption mechanisms. Equilibrium adsorption studies of linear alkyl benzene sulfonate (LAS) show that ionic interaction results in a high maximum adsorption capacity on positively charged adsorbents of 0.6-1.7 gLAS/g. Non-ionic interactions, such as hydrophobic interactions of LAS with non-ionic resins or activated carbons, result in a lower adsorption capacity of 0.02-0.6 gLAS/g. Negatively charged materials, such as cation exchange resins or bentonite clay, have negligible adsorption capacities for LAS. Similar results are obtained for alpha olefin sulfonate (AOS). Cost comparison of different adsorbents shows that an inorganic anion exchange material (layered double hydroxide) and activated carbons are the most cost-effective materials in terms of the amount of surfactant adsorbed per dollar worth of adsorbent.

  3. Correlation and prediction of environmental properties of alcohol ethoxylate surfactants using the UNIFAC method

    DEFF Research Database (Denmark)

    Cheng, Hongyuan; Kontogeorgis, Georgios; Stenby, Erling Halfdan

    2005-01-01

    Environmental properties of one type of nonionic surfactants, the alcohol ethoxylates (polyoxyethylene alcohols), are predicted using the UNIFAC (universal quasi-chemical functional group activity coefficient) method. Various properties are considered; the octanol-water partition coefficient (Kow......), the bioconcentration factor (BCF), and the toxicity. Kow values of alcohol ethoxylates are difficult to measure. Existing methods such as those in commercial software like ACD,ClogP and KowWin have not been applied to surfactants, and they fail for heavy alcohol ethoxylates (alkyl carbon numbers above 12). Thus......, the Kow values are predicted here via UNIFAC and compared to the few available experimental data. Based on the predicted Kow values, a correlation between Kow and hydrophilic-lipophilic balance (HLB) is establi2shed because HLB is a widely used parameter in surfactant applications. Finally, BCF...

  4. Alkylation mechanism of benzene with 1-dodecene catalyzed by Et3NHCl-AlCl3

    Institute of Scientific and Technical Information of China (English)

    2010-01-01

    The isotope exchange method was employed to investigate the catalytic mechanism of ionic liquid in alkylation of benzenes with olefins.It is proposed that alkylation was induced by the Lewis acid AlCl3 which attracted π electrons of 1-dodecene to shift toward 1-carbon,thus forming a carbonium ion.The carbonium ion further reacted with benzenes to form a complex.Due to unstabilit of the complex,a deuterated ring proton was transferred into an electronegative 1-carbon of the side chain to substitute for the AlCl3,accordingly 2-phenyldodecane was generated.

  5. Alkylation of organic aromatic compounds

    Science.gov (United States)

    Smith, L.A. Jr.

    1989-07-18

    Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C[sub 2] to C[sub 10] olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80 C to 500 C, using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms. 1 fig.

  6. Hydrocarbon adsorption in an aqueous environment: A computational study of alkyls on Cu(111)

    Science.gov (United States)

    Montemore, Matthew M.; Andreussi, Oliviero; Medlin, J. Will

    2016-08-01

    Hydrocarbon chains are important intermediates in various aqueous-phase surface processes, such as CO2 electroreduction, aqueous Fischer-Tropsch synthesis, and aqueous phase reforming of biomass-derived molecules. Further, the interaction between water and adsorbed hydrocarbons represents a difficult case for modern computational methods. Here, we explore various methods for calculating the energetics of this interaction within the framework of density functional theory and explore trade-offs between the use of low water coverages, molecular dynamics approaches, and minima hopping for identification of low energy structures. An effective methodology for simulating low temperature processes is provided by using a unit cell in which the vacuum space is filled with water, employing the minima hopping algorithm to search for low-lying minima, and including dispersion (van der Waals) interactions. Using this methodology, we show that a high coverage of adsorbed alkyls is destabilized by the presence of water, while a low coverage of alkyls is stabilized. Solvation has a small effect on the energetics of hydrocarbon chain growth, generally decreasing its favorability at low temperatures. We studied higher temperatures by running molecular dynamics simulations starting at the minima found by the minima hopping algorithm and found that increased temperatures facilitate chain growth. The self-consistent continuum solvation method effectively describes the alkyl-water interaction and is in general agreement with the explicit solvation results in most cases, but care should be taken at high alkyl coverage.

  7. Kinetic analysis of anionic surfactant adsorption from aqueous solution onto activated carbon and layered double hydroxide with the zero length column method

    NARCIS (Netherlands)

    Schouten, Natasja; Ham, Louis G.J. van der; Euverink, Gert-Jan W.; Haan, André B. de

    2009-01-01

    Low cost adsorption technology offers high potential to clean-up laundry rinsing water. From an earlier selection of adsorbents, layered double hydroxide (LDH) and granular activated carbon (GAC) proved to be interesting materials for the removal of anionic surfactant, linear alkyl benzene sulfonate

  8. Selective Antimicrobial Activities and Action Mechanism of Micelles Self-Assembled by Cationic Oligomeric Surfactants.

    Science.gov (United States)

    Zhou, Chengcheng; Wang, Fengyan; Chen, Hui; Li, Meng; Qiao, Fulin; Liu, Zhang; Hou, Yanbo; Wu, Chunxian; Fan, Yaxun; Liu, Libing; Wang, Shu; Wang, Yilin

    2016-02-17

    This work reports that cationic micelles formed by cationic trimeric, tetrameric, and hexameric surfactants bearing amide moieties in spacers can efficiently kill Gram-negative E. coli with a very low minimum inhibitory concentration (1.70-0.93 μM), and do not cause obvious toxicity to mammalian cells at the concentrations used. With the increase of the oligomerization degree, the antibacterial activity of the oligomeric surfactants increases, i.e., hexameric surfactant > tetrameric surfactant > trimeric surfactant. Isothermal titration microcalorimetry, scanning electron microscopy, and zeta potential results reveal that the cationic micelles interact with the cell membrane of E. coli through two processes. First, the integrity of outer membrane of E. coli is disrupted by the electrostatic interaction of the cationic ammonium groups of the surfactants with anionic groups of E. coli, resulting in loss of the barrier function of the outer membrane. The inner membrane then is disintegrated by the hydrophobic interaction of the surfactant hydrocarbon chains with the hydrophobic domains of the inner membrane, leading to the cytoplast leakage. The formation of micelles of these cationic oligomeric surfactants at very low concentration enables more efficient interaction with bacterial cell membrane, which endows the oligomeric surfactants with high antibacterial activity.

  9. FLOTATION DE-INKING OF 50% ONP/ 50% OMG RECOVERED PAPERS MIXTURES USING NONIONIC SURFACTANT, SOAP, AND SURFACTANT/SOAP BLENDS

    Directory of Open Access Journals (Sweden)

    Jeremy Allix

    2010-11-01

    Full Text Available A laboratory flotation column equipped with Venturi aerators and an adjustable froth removal system was used to study the effect of calcium soap and a mixture of calcium soap/alkyl phenol ethoxylate surfactant on ink and fibres transfer during flotation de-inking of a 50% old newprint (ONP / 50% old magazines (OMG recovered papers mixture. Mass transport phenomena determining the yield of the flotation process were interpreted using model equations describing particle removal in terms of flotation, entrainment, and drainage in the froth. A decrease in the ink and mineral fillers flotation rate constant, drainage through the froth, and in fibre entrainment was observed when increasing the surfactant concentration. These trends were consistent with the typical dispersing action of the studied nonionic surfactant. An opposite effect on ink and fillers was observed when using calcium soap alone, and the increase in the flotation rate constant and drainage through the froth were consistent with the collecting and defoaming action of the calcium soap. Moreover, fibre entrainment decreased when increasing the soap concentration. The study of the surfactant/soap mixture highlighted the absence of synergy between the calcium soap and the surfactant.

  10. Polyelectrolyte surfactant aggregates and their deposition on macroscopic surfaces

    Energy Technology Data Exchange (ETDEWEB)

    Voisin, David

    2002-07-01

    Oppositely charged surfactant and polyelectrolyte are present in hair shampoos and conditioners, together with particles (e.g. anti-dandruff agents for scalp) and droplets (e.g. silicone oil for the hair). These are normally formulated at high surfactant concentrations, beyond the flocculation region for the polyelectrolyte concentration used. However, on dilution with water, during application, flocs are formed which carry the particles and droplets to the scalp and hair. The addition of an anionic surfactant to an aqueous solution of cationic polyelectrolyte, at a given concentration, can lead to the formation of polyelectrolyte-surfactant 'particles', in which the surfactant 'binds' to the polyelectrolyte. This occurs from the critical association concentration (CAC), up to the surfactant concentration corresponding to maximum binding. Within this range of surfactant concentrations, the surfactant bound to the polyelectrolyte is thought to associate to form what might be termed 'internal micelles'. Each polyelectrolyte-surfactant particle in the region of the CAC, and just beyond, contains many polyelectrolyte chains, held together essentially by micelle bridges. These particles, however, remain net positively charged, and therefore stable. At the other end of the binding range of the surfactant, so many internal micelles are present that the polymer-surfactant particles are now net negatively charged. Indeed binding stops since no further micelles can be accommodated. Again, the particles are stable. However, there exists a range of surfactant concentrations, lying within the range referred to above, where the net charge is reduced sufficiently that the polymer-surfactant particles will flocculate to form much larger structures. The onset of this second range might be termed the 'critical flocculation concentration' (CFC), and the end, the 'critical stabilisation concentration' (CSC). In this work, the CFC and

  11. Transient exposure of pulmonary surfactant to hyaluronan promotes structural and compositional transformations into a highly active state.

    Science.gov (United States)

    Lopez-Rodriguez, Elena; Cruz, Antonio; Richter, Ralf P; Taeusch, H William; Pérez-Gil, Jesús

    2013-10-11

    Pulmonary surfactant is a lipid-protein complex that lowers surface tension at the respiratory air-liquid interface, stabilizing the lungs against physical forces tending to collapse alveoli. Dysfunction of surfactant is associated with respiratory pathologies such as acute respiratory distress syndrome or meconium aspiration syndrome where naturally occurring surfactant-inhibitory agents such as serum, meconium, or cholesterol reach the lung. We analyzed the effect of hyaluronan (HA) on the structure and surface behavior of pulmonary surfactant to understand the mechanism for HA-promoted surfactant protection in the presence of inhibitory agents. In particular, we found that HA affects structural properties such as the aggregation state of surfactant membranes and the size, distribution, and order/packing of phase-segregated lipid domains. These effects do not require a direct interaction between surfactant complexes and HA and are accompanied by a compositional reorganization of large surfactant complexes that become enriched with saturated phospholipid species. HA-exposed surfactant reaches very high efficiency in terms of rapid and spontaneous adsorption of surfactant phospholipids at the air-liquid interface and shows significantly improved resistance to inactivation by serum or cholesterol. We propose that physical effects pertaining to the formation of a meshwork of interpenetrating HA polymer chains are responsible for the changes in surfactant structure and composition that enhance surfactant function and, thus, resistance to inactivation. The higher resistance of HA-exposed surfactant to inactivation persists even after removal of the polymer, suggesting that transient exposure of surfactant to polymers like HA could be a promising strategy for the production of more efficient therapeutic surfactant preparations.

  12. Alkylated graphene nanosheet composites with polyaniline nanofibers.

    Science.gov (United States)

    Grinou, Ali; Yun, Young Soo; Cho, Se Youn; Jin, Hyoung-Joon

    2011-07-01

    We demonstrate a simple method to prepare alkylated graphene/polyaniline composites (a-GR/PANI) using solution mixing of exfoliated alkyl Iodododecane treated graphene oxide sheets with polyaniline nanofiber; polyaniline nanofibers (PANI) prepared by using rapid mixing polymerization significantly improve the processibility of polyaniline and its performance in many conventional applications. Also, polyaniline nanofibers exhibit excellent water dispersibility due to their uniform nanofiber morphology. Morphological study using SEM and TEM analysis showed that the fibrous PANI in the composites a-GR/PANI mainly adsorbed onto the surface or intercalated between the graphene sheets, due especially to the good interfacial interaction between the alkylated gaphene and the polyaniline nanofibers. The existence of polyaniline nanofibers on the surface of the garphene and the alkylated graphene sheets was confirmed by using FT-IR, FT-Raman and X-ray diffraction analysis. Due to the good interfacial interaction between the alkylated graphene and the polyanilines nanofibers, the composite (a-GR/PANI) exhibited excellent dispersion stability in DMF compared to the same composite (GR/PANI) without alkylation. The electrical conductivity of the (GR/PANI) composite was 9% higher than that of pure PANI and the same weight percent for the composite after alkylation was 13% higher than that of pure PANI nanofibers.

  13. Surfactant adsorption study in sandstone for enhanced oil recovery; Estudo da adsorcao de tensoativos em arenitos para recuperacao avancada de petroleo

    Energy Technology Data Exchange (ETDEWEB)

    Curbelo, Fabiola D.S.; Santanna, Vanessa C.; Barros Neto, Eduardo L. de; Dutra Junior, Tarcilio V.; Dantas Neto, Afonso A. [Universidade Federal do Rio Grande do Norte (UFRN), Natal, RN (Brazil). Dept. de Engenharia Quimica; Garnica, Alfredo I.C. [Universidade Federal da Paraiba (UFPB), Joao Pessoa, PB (Brazil). Dept. de Tecnologia Quimica e de Alimentos; Lucena Neto, Marciano [Universidade Federal do Rio Grande do Norte (UFRN), Natal, RN (Brazil); Dantas, Tereza N.C. [Faculdade Natalense para o Desenvolvimento do RN (FARN), Natal, RN (Brazil)

    2004-07-01

    Adsorption of surfactants from aqueous solutions in porous media is very important in Enhanced Oil Recovery (EOR) of oil reservoirs because surfactant loss due to adsorption on the reservoir rocks weakens the effectiveness of the injected chemical slug in reducing oil-water tension (IFT) and makes the process uneconomical. In this paper, two nonionic surfactants, such as alkyl phenol polyoxyethylene, with different ethoxylation degrees were studied, ENP95 and ENP150. The results of flow experiments of surfactant solutions in porous media showed that adsorption was higher for ENP95 because it has smaller ethoxylation degree than ENP150. This occurs what with increasing length of the head group, the molecules become more hydrophilic and, in associated structures, the steric hindrance between the head groups increases. Generally speaking, adsorption appears to be a cooperative process involving lateral interaction between surfactant and weak interaction with the solid surface. (author)

  14. Interaction of nonionic surfactant AEO9 with ionic surfactants

    Institute of Scientific and Technical Information of China (English)

    ZHANG Zhi-guo; YIN Hong

    2005-01-01

    The interaction in two mixtures of a nonionic surfactant AEO9 (C12H25O(CH2CH2O)9H) and different ionic surfactants was investigated. The two mixtures were AEO9/sodium dodecyl sulfate (SDS) and AEO9/cetyltrimethylammonium bromide (CTAB) at molar fraction of AEO9, αAEO9 =0.5. The surface properties of the surfactants, critical micelle concentration (CMC),effectiveness of surface tension reduction (γCMC), maximum surface excess concentration (Гmax) and minimum area per molecule at the air/solution interface (Amin) were determined for both individual surfactants and their mixtures. The significant deviations from ideal behavior (attractive interactions) of the nonionic/ionic surfactant mixtures were determined. Mixtures of both AEO9/SDS and AEO9/CTAB exhibited synergism in surface tension reduction efficiency and mixed micelle formation, but neither exhibited synergism in surface tension reduction effectiveness.

  15. Surfactant media for constant-current coulometry. Application for the determination of antioxidants in pharmaceuticals

    Energy Technology Data Exchange (ETDEWEB)

    Ziyatdinova, Guzel, E-mail: Ziyatdinovag@mail.ru [Analytical Chemistry Department, A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, Kremlyevskaya, 18, Kazan 420008 (Russian Federation); Ziganshina, Endzhe; Budnikov, Herman [Analytical Chemistry Department, A.M. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, Kremlyevskaya, 18, Kazan 420008 (Russian Federation)

    2012-09-26

    Highlights: Black-Right-Pointing-Pointer Applicability of surfactants in constant-current coulometry is shown for the first time. Black-Right-Pointing-Pointer Reactions of antioxidants with electrogenerated titrants in surfactant media are investigated. Black-Right-Pointing-Pointer Water insoluble antioxidants can be determined in water media with addition of surfactants. Black-Right-Pointing-Pointer Coulometric determination of antioxidants in pharmaceutical dosage forms using surfactants media is developed. - Abstract: Effect of surfactant presence on electrochemical generation of titrants has been evaluated and discussed for the first time. Cationic (1-dodecylpyridinium and cetylpyridinium bromide), anionic (sodium dodecyl sulfate) and nonionic (Triton X100 and Brij{sup Registered-Sign} 35) surfactants as well as nonionic high molecular weight polymer (PEG 4000) do not react with the electrogenerated bromine, iodine and hexacyanoferrate(III) ions. The electrogenerated chlorine chemically interact with Triton X100 and Brij{sup Registered-Sign} 35. The allowable range of surfactants concentrations providing 100% current yield has been found. Chain-breaking low molecular weight antioxidants (ascorbic acid, rutin, {alpha}-tocopherol and retinol) were determined by reaction with the electrogenerated titrants in surfactant media. Nonionic and cationic surfactants can be used for the determination of antioxidants by reaction with the electrogenerated halogens. On contrary, cationic surfactants gives significantly overstated results of antioxidants determination with electrogenerated hexacyanoferrate(III) ions. The use of surfactants in coulometry of {alpha}-tocopherol and retinol provides their solubilization and allows to perform titration in water media. Simple, express and reliable coulometric approach for determination of {alpha}-tocopherol, rutin and ascorbic acid in pharmaceuticals using surfactant media has been developed. The relative standard deviation of the

  16. Janus Gold Nanoparticles from Nanodroplets of Alkyl Thiols: A Molecular Dynamics Study.

    Science.gov (United States)

    Bhandary, Debdip; Valechi, Vasumathi; Cordeiro, Maria Natália D S; Singh, Jayant K

    2017-03-28

    Janus particles provide an asymmetry in structure, which can impart diverse functionalities leading to immense importance in various applications, ranging from targeted delivery to interfacial phenomena, including catalysis, electronics, and optics. In this work, we present results of a molecular dynamics study of the growth mechanism of coating on gold nanoparticles (AuNPs) from droplets of n-alkyl thiols with different chain lengths (C5 and C11) and terminal groups (CH3 and COOH). The effect of chain lengths and functional groups on the formation of a monolayer of alkyl thiols on AuNPs is investigated. A two-step mechanism, initiated by the binding of the droplet to the nanoparticle surface with a time constant on the order of ∼1 ns, followed by the diffusion-driven growth with a larger time constant (on the order of 100 ns), is shown to capture the growth dynamics of the monolayer. It is observed that the time required for complete wetting increases with an increase in the chain length. Moreover, the monolayer formation is slowed down in the presence of carboxyl groups because of strong hydrogen bonding. The kinetics of the n-alkyl thiols coating on the nanoparticles is found to be independent of the droplet size but carboxyl-terminated thiols spread more with increasing droplet size. Furthermore, different time constants for different chains and functional groups yield Janus coating when two droplets of alkyl thiols with different terminal groups are allowed to form monolayers on the nanoparticle. The Janus balance (β) for different combinations of alkyl thiols and nanoparticle sizes varies in the range of 0.42-0.71.

  17. Anomalous diffusion and stress relaxation in surfactant micelles

    Science.gov (United States)

    Dhakal, Subas; Sureshkumar, Radhakrishna

    2017-07-01

    We investigate the mechanisms of anomalous diffusion in cationic surfactant micelles using molecular dynamics simulations in the presence of explicit salt and solvent-mediated interactions. Simulations show that when the counterion density increases, saddle-shaped branched interfaces manifest. In experiments, branched structures exhibit lower viscosity as compared to linear and wormlike micelles. This has long been attributed to stress relaxation arising from the sliding motion of branches along the main chain. Our simulations reveal a mechanism of branch motion resulting from an enhanced counterion condensation at the branched interfaces and provide quantitative evidence of stress relaxation facilitated by branched sliding. Furthermore, depending on the surfactant and salt concentrations, which in turn determine the microstructure, we observe normal, subdiffusive, and superdiffusive motions of surfactants. Specifically, superdiffusive behavior is associated with branch sliding, breakage and recombination of micelle fragments, as well as constraint release in entangled systems.

  18. ADSORPTION OF SURFACTANT ON CLAYS

    Science.gov (United States)

    Surfactants used to enhance remediation of soils by soil washing are often lost in the process. Neither the amount nor the cause of this loss is known. It is assumed that clays present in the soil are responsible for the loss of the surfactant. In this papere, adsorption prope...

  19. Surfactant monitoring by foam generation

    Science.gov (United States)

    Mullen, Ken I.

    1997-01-01

    A device for monitoring the presence or absence of active surfactant or other surface active agents in a solution or flowing stream based on the formation of foam or bubbles is presented. The device detects the formation of foam with a light beam or conductivity measurement. The height or density of the foam can be correlated to the concentration of the active surfactant present.

  20. Surfactant adsorption kinetics in microfluidics

    Science.gov (United States)

    Riechers, Birte; Maes, Florine; Akoury, Elias; Semin, Benoît; Gruner, Philipp; Baret, Jean-Christophe

    2016-10-01

    Emulsions are metastable dispersions. Their lifetimes are directly related to the dynamics of surfactants. We design a microfluidic method to measure the kinetics of adsorption of surfactants to the droplet interface, a key process involved in foaming, emulsification, and droplet coarsening. The method is based on the pH decay in the droplet as a direct measurement of the adsorption of a carboxylic acid surfactant to the interface. From the kinetic measurement of the bulk equilibration of the pH, we fully determine the adsorption process of the surfactant. The small droplet size and the convection during the droplet flow ensure that the transport of surfactant through the bulk is not limiting the kinetics of adsorption. To validate our measurements, we show that the adsorption process determines the timescale required to stabilize droplets against coalescence, and we show that the interface should be covered at more than 90% to prevent coalescence. We therefore quantitatively link the process of adsorption/desorption, the stabilization of emulsions, and the kinetics of solute partitioning—here through ion exchange—unraveling the timescales governing these processes. Our method can be further generalized to other surfactants, including nonionic surfactants, by making use of fluorophore-surfactant interactions.

  1. Studies on Properties of Tetra-p-nitro-tetra-O-alkyl-calix [4] arenes

    Institute of Scientific and Technical Information of China (English)

    LU,Guo-Yuan; SONG,Wei; LIU,Min-Hua; LIU,Fang; JIN,Chuan-Min

    2001-01-01

    This paper reports the properties of the novel tetra- p-nitro- te tra-O-alkyl-calix[4]arenes (alkyl= n-C4H9, 1; n-C8H17, 2; n-C12H25, 3; n-C16H33, 4). X-ray crystallographic analysis and 1H NMR revealed that they exist as pinched-cone confor mation in crystal or cone conformation in soiution. EFISH ex periments at 1064 nm in CHCl3 indicated that tetra-p-nitro-te- tra-O-butyl-calix[4]arene (1) has higher hyperpolarizability βz values than the corresponding reference compound p-nitro phenyl butyl ether, without red shift of the charge transfer band. Compounds 2, 3 and 4 with longer alkyl chains can form monolayer at the air/water.

  2. Cell-specific modulation of surfactant proteins by ambroxol treatment.

    Science.gov (United States)

    Seifart, Carola; Clostermann, Ursula; Seifart, Ulf; Müller, Bernd; Vogelmeier, Claus; von Wichert, Peter; Fehrenbach, Heinz

    2005-02-15

    Ambroxol [trans-4-(2-amino-3,5-dibromobenzylamino)-cyclohexanole hydrochloride], a mucolytic agent, was postulated to provide surfactant stimulatory properties and was previously used to prevent surfactant deficiency. Currently, the underlying mechanisms are not exactly clear. Because surfactant homeostasis is regulated by surfactant-specific proteins (SP), we analyzed protein amount and mRNA expression in whole lung tiss