New approach to the quaternization of chitosan and its amphiphilic derivatives

Regioselective quaternization of chitosan and its amphiphilic derivatives has been carried out by means of reaction with betaine in the presence of the coupling reagent 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) in aqueous media at pH 5.5 ± 0.5. This reaction results in preparation of N-/(trimethylammonio)acetyl/chitosan chloride and its amphiphilic derivatives. The degree of quaternization increases with increasing EEDQ/chitosan ratio and is partly accompanied by N-ethoxycarbonylation. That side-product formation can be minimized by increasing betaine/EEDQ ratio.