Counterion specificity of surfactants based on dicarboxylic amino acids

Bordes, Romain; Tropsch, Juergen; Holmberg, Krister

doi:10.1016/j.jcis.2009.06.032

Cited by 47 publications

(42 citation statements)

References 32 publications

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“…Critical Micelle Concentration CMC of pure HTAB was found to be 0.72 mM (Barai et al, 2019;Manna et al, 2012) while those of disodium salt of N-dodecyl aminomalonate (C 12 MalNa 2 ), N-dodecyl aminoaspartate (C 12 AspNa 2 ), and N-dodecyl aminoglutamate (C 12 GluNa 2 ) were 51.2, 46.3, and 36.45 mM, respectively (Barai et al, 2019;Bordes et al, 2009;Bordes and Holmberg, 2011). With increasing mole fraction of amino acid-based surfactant (α AAS ), CMC values gradually increased from the initial lower value of HTAB as shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Theoretical Approaches on the Synergistic Interaction between Double‐Headed Anionic Amino Acid‐Based Surfactants and Hexadecyltrimethylammonium Bromide

Barai

Mandal

Sultana

et al. 2020

J Surfact & Detergents

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Theoretical investigations on the micellization of mixtures of (i) amino acid‐based anionic surfactants [AAS: N‐dodecyl derivatives of aminomalonate, −aspartate, and ‐glutamate] and (ii) hexadecyltrimethylammonium bromide (HTAB), were carried out at different mole ratios. Variation in the theoretical values of critical micelle concentration (CMC), mole fraction of surfactants in the micellar phase (X), at the interface (Xσ), interaction parameters at the bulk/interface (βR/βσ), ideality/nonideality of the mixing processes, and activity coefficients (f) were evaluated using Rubingh, Rosen, Motomora, and Sarmoria‐Puvvada‐Blankschtein models. CMC values significantly deviate from the theroretically calculated values, indicating associative interaction. With increasing mole fraction of AAS (αAAS), the magnitude of the (βR/βσ) values gradually decreased, considered to attributable to hydrophobic interactions. With increasing αAAS, the micellar mole fraction of HTAB (X2) decreased insignificantly and X2 values were higher than those compared to AAS for all combinations, due to the dominance of HTAB in micelles. Micellar mole fraction at the ideal state of AAS (X1ideal) differed from micellar mole fraction of AAS (X1), indicating nonideality in the mixed micellization process. Gibbs free energy of micellization ( ∆Gm) values are more negative than the free energy of micellization for ideal mixing (∆Gmideal), indicating the micellization process is spontaneous. With increasing αAAS, the enthalpy of micellization (ΔHm) and entropy of micellization (ΔSm) values gradually increased, which indicates micellization is exothermic. The different physicochemical parameters of the mixed micelles are correlated with the variation in the spacer length between the two carboxylate groups of AAS.

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Section: Resultsmentioning

confidence: 99%

Theoretical Approaches on the Synergistic Interaction between Double‐Headed Anionic Amino Acid‐Based Surfactants and Hexadecyltrimethylammonium Bromide

Barai

Mandal

Sultana

et al. 2020

J Surfact & Detergents

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“…Bordes [9] studied the effect of calcium ions on the surface tension of solutions of dicarboxylate surfactants with 1,2 and 3 carbon atom spacers between the carboxylate groups. These were carried out at twice the CMC and it was found that for a surfactant with a three-carbon spacer the surface tension decreased significantly when low concentrations (\0.1 mmol) of calcium ions were added.…”

Section: Effect Of Added Calcium Ionsmentioning

confidence: 99%

“…A biosynthetic route has led to the formation of one such surfactant [8]. Bordes [9] has made a number of N-lauryl dicarboxylic acids via the Schotten-Baumann reaction and studied their counterion specificity. Other recent examples of novel amino acid surfactants include zwitterionic threonine surfactants [10] and vesicle-forming L-histidine surfactants [11].…”

Section: Introductionmentioning

confidence: 99%

Glycine Surfactants Derived from Dodecenyl Succinic Anhydride

Dix

Moon

2011

J Surfact & Detergents

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We report the synthesis and properties of two surfactants with a novel head group based on glycine. A monocarboxylic surfactant N‐glycine methyl ester (2‐dodecen‐1‐yl succinamic acid) (I) was prepared by ring opening of an n‐alkyl succinic anhydride. Hydrolysis of the ester functionality yields a dicarboxylic acid II. The sodium salts of I and II were effective surfactants at neutral pH giving a low minimum surface tension (<30 mN m−1 at 20 °C). At high pH (~12) the surface activity of both surfactants is reduced compared to neutral pH, indicating that at neutral pH an ‘acid soap’ is formed. The pKa of the acid form of the surfactants was determined. Addition of calcium ions reduced the CMC of II but did not reduce the surface tension above the CMC. The resistance of II to calcium ion precipitation was measured at pH 7.

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“…In another article Preiss et.al proposed a new method for the preparation of chiral polymeric nanoparticles based on the use of polymerizable chiral surfactants. The preparation and application of chiral polymerizable surfactants, also called surfmers have been investigated in recent years . In the above article, the authors focus on the synthesis of chiral surfmers of various optically active surfactants and compare their behavior in the preparation of polymer particles by miniemulsion polymerization.…”

Section: Introductionmentioning

confidence: 99%

Chiral Polymers and Polymeric Particles for Enantioselective Crystallization

Medina

Mastai

2018

Israel Journal of Chemistry

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Chiral polymers and chiral polymeric particles have emerged as a new and exciting field of research in recent years mainly due to their possibly applications in chiral chemistry. This paper reviews the present state of the art regarding production techniques for the synthesis and applications of chiral polymeric particles. The main methods for preparing of chiral polymeric particles such as: direct polymerization, emulsion, precipitation, and suspension polymerization of chiral monomers, are reviewed. Moreover, in this article we also present the use of chiral polymers as chiral templates for the synthesis of chiral mesoporous materials. In this review we highlighted the properties and parameters involved in the preparation of these chiral polymeric materials. The present review focuses mainly on the use of chiral polymer and chiral polymeric particles for enantioselective crystallization and enantioseparation. References of the most relevant literature published by various research groups are provided. Anyway, it is clear that chiral polymeric particles are a distinctive type of chiral nanomaterials that can find many new application in other fields like, chiral drug delivery systems, enantioselective catalysis. We hope that this review article will inspired new researchers in this field and will boost the research dealing on chiral polymeric particles especially in their implementation in new areas in chiral chemistry.

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Counterion specificity of surfactants based on dicarboxylic amino acids

Cited by 47 publications

References 32 publications

Theoretical Approaches on the Synergistic Interaction between Double‐Headed Anionic Amino Acid‐Based Surfactants and Hexadecyltrimethylammonium Bromide

Theoretical Approaches on the Synergistic Interaction between Double‐Headed Anionic Amino Acid‐Based Surfactants and Hexadecyltrimethylammonium Bromide

Glycine Surfactants Derived from Dodecenyl Succinic Anhydride

Chiral Polymers and Polymeric Particles for Enantioselective Crystallization

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