Synthesis and properties of lipoamino acid/fatty acid mixtures. Influence of the amphiphilic structure.

Abstract

The acylation of amino acids by acid chlorides with from 8 to 12 carbon atoms, in alkaline aqueous medium following Shotten-Baumann reaction, results in sodium salts of Nα-acylamino acids and fatty acids mixture. These lastest are present in proportion from 40 to 60%. These compositions represent mixtures of amphiphilic anionic surfactants. They contribute together to the properties of the formulation. Measurements of the surface-active properties of these formulations, such as critical micelle concentration (CMC), surface tension at the CMC (TS), foaming capacity (FC) and foaming stability (FS), show that surfactant mixtures with the longest chain have the most desirable properties. They are comparable to commercial petroleum-based surfactants. Thus, the CMC, TS and CM values of the formulation obtained starting from leucine and dodecanoyl chloride (310 mg/L, 30.1 mN/m and 200%, respectively) are similar, even better than, sodium dodecylsulfate (290 mg/L, 39.1 mN/m and 230%, respectively