Catanionic Organogelators Derived from D-Sorbitol and Natural Fatty Acids

Abstract

Several catanionic organogelators derived from 1,3 :2,4-bis-O-(p-aminobenzylidene)-D-sorbitol (p-NH2-DBS) and hydroxy derivatives of natural fatty acids were synthesized, characterized and their gelation ability was evaluated. SEM observations of the xerogels formed by association of 1,3 :2,4-bis-O-(p-aminobenzylidene)-D-sorbitol and 12-hydroxystearic acid showed important modifications in the morphology and depend upon the nature of solvent as compared with the xerogels formed by each individual organogelator.

1,3:2,4-Dibenzylidene-d-sorbitol (DBS) and its derivatives – efficient, versatile and industrially-relevant low-molecular-weight gelators with over 100 years of history and a bright future

“…6, p-NH 3 + -DBS), counterbalanced by the carboxylate anions of a natural fatty acid; stearic acid (SA), 12-hydroxystearic acid (HSA), erythro-9,10-dihydroxystearic acid (DHSA) or erythro, erythro-9,10,12,13tetrahydroxystearic acid (THSA). 34 Although salt formation impaired the inherent gelation ability of p-NH 2 -DBS, which was reasoned to be due to the disruptive effect of the positive charge on the stacking of the benzylidene groups, the complex with HSA formed stable organogels in some solvents. It was suggested that this could be attributed to the fact that HSA, a natural fatty acid and active component of castor oil, is an active gelator in its own right.…”