Journal of Colloid and Interface Science, Vol.173, No.1, 49-54, 1995
Preparation, Properties, and Applications of Vesicle-Forming Cleavable Surfactants with a 1,3-Dioxane Ring
A series of quaternary ammonium vesicle-forming surfactants was prepared by cyclization of 2,2-dialkyl-1,3-propanediols with 3-bromopropanal, followed by reaction with refluxing triethylamine. The critical vesicle concentrations of these surfactants fell in the range of 10(-5)-10(-6) M, which were smaller than the critical micelle concentrations of their counterparts containing only one alkyl chain. The fact that the destructibility of these surfactants was similar to their counterparts bearing only one alkyl chain gave further evidence to the conclusion that the morphology, micelle or vesicle, has little effect on the hydrolytic properties. The sonicated dispersions of these surfactants were single-compartment vesicles with their diameters ranging from 200 to 600 Angstrom. The reactions of TEMPO-12 with VC and TEMPO-OH with VC-12 in the vesicle of 4b prepared by sonication or stirring were studied by ESR spectroscopy with stopped-flow technique. The reaction behavior was explained by the electrostatic attraction of VC/VC-12 by the cationic head groups of surfactants, the flip-flop motion and diffusion of the spin probe/VC-12, and the morphology of these vesicles.
Keywords:ELECTRON-SPIN-RESONANCE;DESTRUCTIBLE SURFACTANTS;MONOLAYER PROPERTIES;CHEMICAL-STRUCTURE;BILAYER-MEMBRANES;AQUEOUS-SOLUTION;VITAMIN-C;MICELLES;BEARING;ACID