Surface active N‐acylglutamate: II. Physicochemical properties of long chain N‐acylglutamic acids and their sodium salts

Takehara, Masahiro; Moriyuki, H.; Yoshimura, Ippei; Yoshida, Ryonosuke

doi:10.1007/bf02633782

Cited by 54 publications

(19 citation statements)

References 8 publications

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“…(Figures 2(a) and 2(b) ) are essentially similar except in the solid melting temperature at high surfactant concentration. The reason for that may lie in the different molecular packing and intermolecular interactions in the solid state (31,32). In the micellar solution or in the liquid crystalline states, surfactant molecules are comparatively far away, and therefore, there is no significant difference in the molecular interaction between surfactant molecules in both, DL-KDA and L-KDA systems.…”

Section: )mentioning

confidence: 99%

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Acharya¹,

López‐Quintela²,

Kunieda³

et al. 2003

J. Oleo Sci.

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Section: )mentioning

confidence: 99%

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Acharya¹,

López‐Quintela²,

Kunieda³

et al. 2003

J. Oleo Sci.

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“…For CZE determination, such mobility changes significantly affect both peak assignment for qualitative analysis and peak area measurement for quantitative analysis. Takehara et al 17 reported that the critical micelle concentration (cmc) estimated by a conductivity method for C 12 (MW: 351) was 10.6 mM at 40˚C. It should be noted that the sample concentrations examined here were beyond the cmc (>3500 ppm).…”

Section: Effect Of Addition Of Organic Solvents On Separationmentioning

confidence: 65%

Determination of N-Acyl-l-glutamates Surfactants by Capillary Electrophoresis Using Organic Modifier

Kunimasa

Kameyama

1999

ANAL. SCI.

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Capillary electrophoresis (CE) has become a powerful technique for the analysis of a wide variety of inorganic and organic compounds. 1 The technique provides rapid resolution and minimum solvent consumption and is appropriate to samples that are difficult to separate by gas or liquid chromatography.Anionic surfactants are now indispensable additives as dispersants and detergents in a variety of industrial and consumer applications. Usually commercial surfactants are homologous mixtures where the hydrocarbon chain may vary from C 8 to C 20 . The need to determine anionic surfactants and their composition in raw materials and product formulations is obvious for quality control and for extensive applications of the surfactants. Gas chromatography (GC) 2 and liquid chromatography (LC) [3][4][5][6] have been considered to meet this requirement. In GC, however, time-consuming and often complex derivatization procedures to convert into volatile compounds are required. LC methods with anion exchangers or reversed phases have been widely used, but there are problems associated with strong sorption or incomplete separation of the components.Recently, a number of reports have appeared on the usefulness of CE techniques for anionic surfactants; 7-11 however, few applications besides alkanesulfonates and alkyl sulfates surfactants have been reported. Since CE methods have the potential to be applicable to most classes of anionic surfactants, further development in this method would be of widespread interest. The present paper reports the CE analysis of C 12 -C 18 Nacyl-L-glutamates surfactants, widely used for excellent cosmetic ingredients because of lack of irritation for human skin and good biodegradability. 13 This approach is important for rapid resolution of the homologous mixture, because the alkyl length closely relates to the solubility, Krafft point, critical micelle concentration, and foaming power of the studied surfactants. We describe here the optimization of the operating conditions for the determination of the surfactants using capillary zone electrophoresis (CZE). In particular, we discuss the effects of addition of organic solvents to the buffer solution on the separation of the analytes. Experimental ApparatusAll electropherograms were generated using a CAPI-3100 capillary electrophoresis instrument (Otsuka Electronics, Osaka, Japan). Fused-silica capillaries with 75 µm i.d. were used as separation tubes. The total capillary length was 50 cm and the effective capillary length was 37.8 cm. ReagentsThree kinds of monosodium N-acyl-L-glutamates for cosmetic ingredients were supplied by Ajinomoto Co. (Tokyo, Japan). Their acyl radicals were as follows: lauroyl (C 12 ); myristoyl (C 14 ); mixture of palmitoyl and stearoyl (C 16 -C 18 ). Sodium tetraborate, used for an electrolyte, was of reagent grade with 99% purity from Kokusan Chemical (Tokyo, Japan). All other reagents were of reagent grade from different manufacturers, and were used without further purification. Research & Development Division, KOSÉ Corp...

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“…Generally, they have been prepared from fatty acid chlorides and amino acids [10][11][12][13][14][15] , where acid halides are used to introduce the hydrophobic groups. However, on the view point of availability of starting materials, it may not be easy to obtain optically active fatty acids compared to the availability of optically active alcohols.…”

Section: Resultsmentioning

confidence: 99%

“…Among them, sodium salts of Nacyl amino acids are anionic surfactants with good biodegradability [1][2][3] , skin compatibility and antibacterial activity [4][5][6][7][8][9] and have been widely used in detergent, shampoo, cosmetic and food formulations. They are usually prepared from fatty acid chlorides and either pure amino acids or protein hydrolysates [10][11][12][13][14][15] . However, as the acid halides are used to introduce the hydrophobic groups, it may not be easy to vary the hydrophobic groups on the view point of availability.…”

Section: Introductionmentioning

confidence: 99%

A Novel Synthesis of N-Alkoxycarbonyl Amino Acids and Surfactant Properties of Their Sodium Salts

2010

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N-Acyl amino acids have been prepared from fatty acid chlorides and amino acids, but it may not be easy to vary the hydrophobic groups on the view point of availability. In this work, instead of acid halides, long alkyl chloroformates were prepared by the facile reaction of alcohols and triphosgene as an induction agent of hydrophobic group on amino acids. N-Alkoxycarbonyl amino acids were synthesized from alkyl chloroformate and amino acids under Schötten-Baumann reaction condition with some modification. Surfactant properties of their sodium salts were studied by surface tension measurements, dynamic light scattering and foaming test, and compared with those of N-acyl amino acids. Sodium salts of N-alkoxycarbonyl amino acids showed an excellent surface tension lowering ability comparable to N-acyl amino acids, and they also exhibited good foaming ability and stability.

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Surface active N‐acylglutamate: II. Physicochemical properties of long chain N‐acylglutamic acids and their sodium salts

Cited by 54 publications

References 8 publications

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Phase Behavior and Effect of Enantiomerism on Potassium N -Dodecanoyl Alaninate/Water/Decanol Systems

Determination of N-Acyl-l-glutamates Surfactants by Capillary Electrophoresis Using Organic Modifier

A Novel Synthesis of N-Alkoxycarbonyl Amino Acids and Surfactant Properties of Their Sodium Salts

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