Synthesis and Surface-Active Properties of 1, 3-Bis- [2- (acylamino) ethyldimethylammonio] -2-hydroxypropane Dichloride

Abstract

Novel bis [quaternary amidoammonium] salts were easily prepared by reactions of 2- (acylamino) ethyldimethylamine with epichlorohydrin and should prove chemically hydrolyzable due to amido groups in the lipophilic chains. Surface-active properties were determined and compared with those of 2- (acylamino) ethyltrimethylammonium chloride, and mono- and bis [quaternary alkylammonium] salts. Bis [quaternary amidoammonium] salts each possessing 10 to 14 carbon atoms in the acyl chain showed good water solubility. Cmc of 1, 3-bis [2- (dodecanoylamino) ethyldimethylammonio] -2-hydroxy-propane dichloride was smaller by about one order of magnitude than that of 2- (dodecanoylamino) ethyltrimethylammonium chloride with the same acyl chain length, and smaller by about two orders than that of conventional dodecyltrimethylammonium chloride. The bis [quaternary amidoammonium] salts showed lower surface tension at cmc (γcmc) than other mono- and bis [quaternary alkylammonium] salts. Foaming ability and foam stability of bis [quaternary amidoammonium] salts having dodecanoyl or tetradecanoyl group in the lipophilic chain were quite high.