Chemical modification of chitosan. Part 15: synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate |
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Authors: | Sashiwa Hitoshi Kawasaki Norioki Nakayama Atsuyoshi Muraki Einosuke Yajima Hirofumi Yamamori Naoki Ichinose Yoshifumi Sunamoto Junzo Aiba Sei-ichi |
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Affiliation: | 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. |
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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. |
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Keywords: | Chitosan N-Carboxyethylchitosan ethyl ester Michael reaction Amidation |
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