Synthesis, Physicochemical and Antimicrobial Properties of 3-(3-Alky1-2oxoimidazolidine-1-y1)-1-propanesulfonic Acids

Abstract

A new class of surfactants, 3-(3-alkyl-2-oxoimidazolidine-1-yl)-1-propanesulfonic acids [1], were prepared in high yields by the N-sulfopropylation of 1-alkyl-2-imidazolidinones (Table 2) with 1, 3-propanesultone by use of sodium hydride as a base (Table 3). The sulfonic acid derivatives [1] had good surface-active properties; particularly, the C₁₂, C₁₄, and C₁₆ derivatives were as good as or superior to sodium dodecylbenzenesulfonate (DBS)in the solubilization of Orange OT in water (Fig.3) and in the emulsification of liquid para ffffin in water (Fig.2). They showed poor to moderate foaming ability and foam stability (Table 5). A linear relation was observed between the logarithm of the critical micelle concentration and the number of carbon atoms in the alkyl chain of [1]. The compounds were also tested for the antimicrobial activity against a gram -positive bacterium, Staphylococcus aureus, a gram-negative bacterium, Escherichia coli, and a fungus, Asper gillus oryzae. All the compounds were virtually ineffective against S. aureus and E. coli, but the C₁₄ and C₁₆ homologs had noticeable antifungal activity.