Preparation of N, N, N-trimethyl chitosan via a novel approach using dimethyl carbonate

Abstract

N,N,N-trimehtyl chitosan (TMC) is a water-soluble derivate of chitosan, which has been widely used as a biomedical material due to its excellent biocompatibility, biodegradability and bacterial properties. To date, TMC can only be prepared by the quaternization of chitosan using alkyl halide or dimethyl sulfate. However, alkyl halide and dimethyl sulfate are highly toxic, cancerigenic for humans, and harmful to the environment. This paper puts forward a novel approach to preparing TMC using dimethyl carbonate as a methylation reagent in an ionic liquid. The as-synthesized O-methyl-free TMC was characterized using NMR, FTIR, XRD and TG analyses. The results showed that TMC with a degree of quaternization of 9.11% was successfully obtained and the crystallinity of chitosan decreased with the increasing degree of N-methylation, the thermal stability of TMC was lower than that of chitosan. Furthermore, the effects of the dose of ionic liquid and dimethyl carbonate were disscussed.