Synthesis of Phenylcarbamoyl Chitosan via Complexation of Chitosan with Surfactant

In this study, an attempt was made to synthesize phenylcarbamoyl chitosan (PC-Cts) via complexation of chitosan with surfactant sodium dodecyl sulfate (SDS). SDS-chitosan complex was prepared simply by mixing acid solutions of chitosan and SDS. The complex was then reacted with phenyl isocyanate in dimethyl sulfoxide to yield PC-Cts. The molecular structures of the products were characterized by 1H NMR spectroscopy. In 1H NMR spectra of product samples, resonance signals characteristic of phenylcarbamoyl groups appeared together with those of chitosan. From this result, it was reasonably suggested that phenylcarbamoylation of chitosan was achieved by the procedure employed in this study. The 1H NMR data were also used to determine the substitution parameters, including degree of substitution (DS), molar substitution (MS), degree of polymerization in the side chains (DPS), and residual SDS content. The parameters varied with changes in reaction conditions. From these molecular characterization, the reaction pathway was proposed.