Surfactants Derived from Amino Acids. III.

Yoshida, Ryonosuke; Baba, Keiko; Saito, Tatsuhiro; YOSHIMURA, Ippei

doi:10.5650/jos1956.25.404

Cited by 11 publications

(6 citation statements)

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“…Ring tensiometer [19,20] The discrepancies between the results reported above can be attributed to the differences in LAE solution composition. They can contain surface-active residuals from LAE synthesis that are also the surfactant hydrolysis products.…”

Section: Introductionmentioning

confidence: 95%

Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

et al. 2021

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Ethyl lauroyl arginate (LAE) is an amino acid-based cationic surfactant with low toxicity and antimicrobial activity. It is widely used as a food preservative and component for food packaging. When stored, LAE decomposes by hydrolysis into surface-active components Nα-lauroyl–l-arginine (LAS) or dodecanoic (lauric) acid. There are only a limited number of reports considering the mechanism of surface activity of LAE. Thus, we analysed the surface tension isotherm of LAE with analytical standard purity in relation to LAE after prolonged storage. We used quantum mechanical density functional theory (DFT) computations to determine the preferred hydrolysis path and discuss the possibility of forming highly surface-active heterodimers, LAE-dodecanoate anion, or LAE-LAS. Applying molecular dynamics simulations, we determined the stability of those dimers linked by electrostatic interactions and hydrogen bonds. We used the adsorption model of surfactant mixtures to successfully describe the experimental surface tension isotherms. The real part surface dilational modulus determined by the oscillation drop method follows a diffusional transport mechanism. However, the nonlinear response of the surface tension could be observed for LAE concentration close to and above Critical Micelle Concentration (CMC). Nonlinearity originates from the presence of micelles and the reorganisation of the interfacial layer.

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Section: Introductionmentioning

confidence: 95%

Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

et al. 2021

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“…In recent years, Nacylarginine ethyl ether salts with a guanidine group and lauroyl amidobutylguanidine acetate (LAG) have been developed and found to be antibacterial [5] and highly adsorbable onto hair [6]. Thus, LAG was applied to hair conditioner in the form of LAG/ higher alcohol complex to be strongly adsorbed on the hair surface [7].…”

Section: Introductionmentioning

confidence: 99%

Effect of amidoalkyl group as spacer on aggregation properties of guanidine-type surfactants

Miyake

Oyama

2009

Journal of Colloid and Interface Science

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“…N-Acylarginine esters and lauroylamide butylguanidine acetate (LAG), both having a guanidine group in their molecules, have recently been synthesized and found to be antibacterial and highly adsorptive to hair. 5,6 As for LAG, it has been applied as a hair conditioner that allows LAG/higher alcohol complex to strongly adsorb on the hair surface. 7 Meanwhile, there has been little research on the physicochemical properties of G-type surfactants, 8 and the characteristics of the guanidine group still remain to be studied further.…”

Section: Introductionmentioning

confidence: 99%

Self-Assembling of Guanidine-Type Surfactant

2008

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Self-assembling characteristics of dodecylguanidine hydrochloride (C 12G), a cationic surfactant with a guanidine group in its molecule, were investigated and compared with those of dodecyltrimethylammonium chloride (DTAC) and sodium dodecylsulfate (SDS). Introduction of a guanidine group into the surfactant molecule was found to increase its assembly formability more than that of the trimethylammonium group on the basis of the experimental results on the phase diagram, Kraft point, area occupied per molecule at the air-water interface, and micellar aggregation number of C 12G. Thermodynamic parameters for micelle formation suggested that an attractive force acts between guanidine groups of C 12G molecules to facilitate their assembly formation. The presence of this force was evidenced by changes in the (1)H NMR and IR spectra before and after micelle formation of the guanidine-type (G-type) surfactant, indicating that the increased assembly formability is caused by an increase in hydrogen bonding between guanidine groups of the surfactant via water molecules.

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Surfactants Derived from Amino Acids. III.

Cited by 11 publications

References 0 publications

Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

Effect of amidoalkyl group as spacer on aggregation properties of guanidine-type surfactants

Self-Assembling of Guanidine-Type Surfactant

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