Synthesis of a novel polymeric surfactant by reductive N-alkylation of chitosan with 3-O-dodecyl-D-glucose

A novel chitosan-based polymeric surfactant, DG-chitosan, was prepared via reductive N-alkylation of chitosan with 3-O-dodecyl-D-glucose in acetate buffer (pH 4.3, 0.1 M)-methanol in the presence of sodium cyanoborohydride (NaBH3CN). DG-chitosan was swelling in water, partly dissolvable in pyridine and DMF, and completely soluble in 0.1% aqueous acetic acid. H-1 and C-13 NMR spectroscopic analyses in 2% acetic acid-d(4)-methanol-d(4) together with elemental analysis showed the degree of substitution was 27%. Formation of polymeric micelles was observed by use of pyrene as a fluorescent probe, and the critical aggregation concentration (CAC) of DG-chitosan was marked equal to 28.1 mg/L. (C) 2003 Published by Elsevier Ltd.