界面活性剤との錯形成を経由したフェニルカルバモイルキトサンの合成と置換パラメータの解析

摘要

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 ~(1)H NMR spectroscopy. In ~(1)H 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 ~(1)H 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 (DP_(S) ), and residual SDS content. The parameters varied with changes in reaction conditions. From these molecular characterization, the reaction pathway was proposed.