Cleavable double-chain surfactants with one cationic and one anionic head group that form vesicles

Cleavable surfactants 1 (2-(2-[1-[2-carboxylatoethyl]alkylidene])hydrazino-N-alkyl-N,N-dimethyl-2-oxoethanaminium bromide: a, alkyl = dodecyl; alkylidene = tridecylidene; b, alkyl = tetradecyl; alkylidene = pentadecylidene), which contain two alkyl chains and two head groups, have been prepared by the reaction of surfactants 2 (2-hydrazino-N-alkyl-N,N-dimethyl-2-oxoethanaminium bromide: a, alkyl = dodecyl; b, alkyl = tetradecyl) with keto acids 3 (a, 4-oxohexadecanoic acid; b, 4-oxooctadecanoic acid). Surfactants 1 form vesicles, including giant vesicles observed by optical microscopy, and undergo acid-catalyzed hydrolysis at pH ca. 3, to give 2 and 3.