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Chemical modification of chitosan. Part 15: synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate
Authors:Sashiwa Hitoshi  Kawasaki Norioki  Nakayama Atsuyoshi  Muraki Einosuke  Yajima Hirofumi  Yamamori Naoki  Ichinose Yoshifumi  Sunamoto Junzo  Aiba Sei-ichi
Institution:Green Biotechnology Research Group, The Special Division for Human Life Technology, National Institute of Advanced Industrial Science and Technology, 1-8-31 Midorigaoka, Ikeda, 563-8577, Osaka, Japan.
Abstract:The Michael type reaction of chitosan with ethyl acrylate has been investigated. Although this reaction was quite slow in the case of chitosan, the reiteration of the reaction was an effective means for increasing the degree of substitution (DS) of ethyl ester. The N-carboxyethylchitosan ethyl ester as an intermediate was successfully substituted with various hydrophilic amines, although the simultaneous hydrolysis of the ester to carboxylic acid also occurred. Water-soluble chitosan derivatives were obtained by substitution with hydroxyalkylamines and diamines.
Keywords:Chitosan  N-Carboxyethylchitosan ethyl ester  Michael reaction  Amidation
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