Wormlike Micelle Formation by Acylglutamic Acid with Alkylamines

Sakai, Kenichi; Nomura, K.; Shrestha, Rekha Goswami; Endo, Takeshi; Sakamoto, Kazutami; Sakai, Hideki; Abe, Masahiko

doi:10.1021/la303745p

Cited by 43 publications

(26 citation statements)

References 29 publications

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“…Herein, we showed that highly viscoelastic wormlike micellar solutions were obtained using relatively low concentrations of the amino acid-based surfactants 0.3 wt . Additionally, we confirmed that an amino acid-based monomeric surfactant, dodecanoylglutamic acid, yields aqueous solutions of wormlike micelles by forming a complex that contains tertiary and secondary alkylamines 16 . The alkylamine compounds act as an organic counterion to neutralize the carboxylic acid headgroups of dodecanoylglutamic acid, as well as to control the packing parameter for wormlike micelles.…”

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confidence: 62%

Effects of Spacer Chain Length of Amino Acid-Based Gemini Surfactants on Wormlike Micelle Formation

Sakai¹,

Nomura²,

Shrestha³

et al. 2014

J. Oleo Sci.

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We studied the effects of the spacer chain length of amino acid-based gemini surfactants on the formation of wormlike micelles in aqueous solutions. The surfactants used were synthesized by reacting dodecanoylglutamic acid anhydride with diamine compounds (ethylenediamine, pentanediamine, and octanediamine), and were abbreviated as 12-GsG-12 (s: the spacer chain length of 2, 5, and 8 methylene units). These surfactants yielded viscoelastic wormlike micellar solutions at pH 9 upon mixing with a cationic monomeric surfactant, hexadecyltrimethylammonium bromide (HTAB). We found that the rheological behavior was strongly dependent on the spacer chain length and HTAB concentration. When the shortest spacer chain analogue (12-G2G-12) was used, an increased HTAB concentration resulted in the following structural transformations of the micelles: (i) spherical or rodlike micelles; (ii) anionic wormlike micelles exhibiting a transient network structure; (iii) anionic wormlike micelles with a micellar branching or interconnected structure; and (iv) cationic wormlike micelles. Similarly, when the middle spacer chain analogue (12-G5G-12) was used, a structural transformation from anionic to cationic wormlike micelles occurs; however, molecular aggregates with a lower positive curvature were also formed in this transition region. When the longest spacer analogue (12-G8G-12) was used, the formation of cation-rich molecular aggregates was not observed. These transition behaviors were attributed to the packing geometry of the gemini surfactants with HTAB. Additionally, as the spacer chain length increased, the zero-shear viscosity in the anionic wormlike micellar region decreased, suggesting limited one-dimensional micellar growth of spherical, rodlike, or anionic wormlike micelles.

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supporting

confidence: 62%

Effects of Spacer Chain Length of Amino Acid-Based Gemini Surfactants on Wormlike Micelle Formation

Sakai¹,

Nomura²,

Shrestha³

et al. 2014

J. Oleo Sci.

Self Cite

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“…However, the essential difference between the polymers with covalent bonds and WLMs is that the bonds are transient in the latter case. The self-regenerating nature of WLMs after subjecting these systems to flow or deformation makes them extremely useful in many industrial applications including oil production, drag reduction agent, and drug delivery [ 14 , 15 , 16 ].…”

Section: Introductionmentioning

confidence: 99%

The Formation of pH-Sensitive Wormlike Micelles in Ionic Liquids Driven by the Binding Ability of Anthranilic Acid

You

Zhang

Wang

et al. 2015

IJMS

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Wormlike micelles are typically formed by mixing cationic and anionic surfactants because of attractive interactions in oppositely charged head-groups. The structural transitions of wormlike micelles triggered by pH in ionic liquids composed of N-alkyl-N-methylpyrrolidinium bromide-based ILs (ionic liquids) and anthranilic acid were investigated. These structures were found responsible for the variations in flow properties identified by rheology and dynamic light scattering, and account for the structures observed with cryogenic transmission electron microscopy (Cryo-TEM). High-viscosity, shear-thinning behavior, and Maxwell-type dynamic rheology shown by the system at certain pH values suggested that spherical micelles grow into entangled wormlike micelles. Light scattering profiles also supported the notion of pH-sensitive microstructural transitions in the solution. Cryo-TEM images confirmed the presence of spherical micelles in the low-viscosity sample and entangled wormlike micelles in the peak viscosity sample. Nuclear magnetic resonance spectroscopy analysis revealed that the pH sensitivity of ionic liquid systems originated from the pH-dependent binding ability of anthranilic acid to the cationic headgroup of ionic liquids.

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“…These are attributed to the role of the intermolecular hydrogen bonding which occurs between the hydroxyl substituted spacers. Recently, it was found that pH-induced gemini-like surfactants formed by single-chain surfactant and a building block with two binding sites could also aggregate into wormlike micelles [ 37 , 38 , 39 ]. Feng et al [ 37 ] constructed a pH-switchable wormlike micellar system by mixing N -erucamidopropyl- N , N -dimethylamine and maleic acid with a molar ratio of 2:1.…”

Section: Introductionmentioning

confidence: 99%

pH-Responsive Rheological Properties and Microstructure Transition in Mixture of Anionic Gemini/Cationic Monomeric Surfactants

et al. 2021

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Surfactant aggregates have long been considered as a tool to improve drug delivery and have been widely used in medical products. The pH-responsive aggregation behavior in anionic gemini surfactant 1,3-bis(N-dodecyl-N-propanesulfonate sodium)-propane (C12C3C12(SO3)2) and its mixture with a cationic monomeric surfactant cetyltrimethylammonium bromide (CTAB) have been investigated. The spherical-to-wormlike micelle transition was successfully realized in C12C3C12(SO3)2 through decreasing the pH, while the rheological properties were perfectly enhanced for the formation of wormlike micelles. Especially at 140 mM and pH 6.7, the mixture showed high viscoelasticity, and the maximum of the zero-shear viscosity reached 1530 Pa·s. Acting as a sulfobetaine zwitterionic gemini surfactant, the electrostatic attraction, the hydrogen bond and the short spacer of C12C3C12(SO3)2 molecules were all responsible for the significant micellar growth. Upon adding CTAB, the similar transition could also be realized at a low pH, and the further transformation to branched micelles occurred by adjusting the total concentration. Although the mixtures did not approach the viscosity maximum appearing in the C12C3C12(SO3)2 solution, CTAB addition is more favorable for viscosity enhancement in the wormlike-micelle region. The weakened charges of the headgroups in a catanionic mixed system minimizes the micellar spontaneous curvature and enhances the intermolecular hydrogen-bonding interaction between C12C3C12(SO3)2, facilitating the formation of a viscous solution, which would greatly induce entanglement and even the fusion of wormlike micelles, thus resulting in branched microstructures and a decline of viscosity.

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Wormlike Micelle Formation by Acylglutamic Acid with Alkylamines

Cited by 43 publications

References 29 publications

Effects of Spacer Chain Length of Amino Acid-Based Gemini Surfactants on Wormlike Micelle Formation

Effects of Spacer Chain Length of Amino Acid-Based Gemini Surfactants on Wormlike Micelle Formation

The Formation of pH-Sensitive Wormlike Micelles in Ionic Liquids Driven by the Binding Ability of Anthranilic Acid

pH-Responsive Rheological Properties and Microstructure Transition in Mixture of Anionic Gemini/Cationic Monomeric Surfactants

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