, Volume 73, Issue 1, pp 31-37

α-sulfonated fatty acid esters: II. Solution behavior of α-sulfonated fatty acid polyethylene glycol esters

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Abstract

Sodium α-sulfonated, fatty acid polyethylene glycol monoesters [C m H2m+1CH(SO3Na)COO(C2H4O) n H] and diesters [C m H2m+1CH(SO3Na)COO(C2H4O) n COCH(SO3Na)C m H2m+1], wherem=10–16 andn=1–35, were prepared by esterification of α-sulfonated, fatty acids with polyethylene glycols, followed by neutralization with NaOH. Crude products were purified by reversed-phase column chromatography on an octadecyl-modified silica gel. Characteristic solution behavior of these α-sulfonated fatty acid esters was, examined, and the following features were observed. All monoesters prepared in this work had Krafft points below 0°C and also possessed good calcium stabilities. Critical micelle concentrations of the monoesters increased monotonously, as a rule, with an increase in the number of oxyethylene units. These results suggest that the polyethylene glycol residue of the monoester behaves as a hydrophile. On the other hand, diesters possessed high water solubility, low foamability, and critical micelle concentrations that were lower by a factor of ten compared to those of the monoesters.