Chemical modification of chitosan. Part 15: synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate.
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.
Sashiwa
Hitoshi
H
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.
Kawasaki
Norioki
N
Nakayama
Atsuyoshi
A
Muraki
Einosuke
E
Yajima
Hirofumi
H
Yamamori
Naoki
N
Ichinose
Yoshifumi
Y
Sunamoto
Junzo
J
Aiba
Sei-ichi
S
D000179:Acrylates / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D048271:Chitosan / Q000031:analogs & derivatives; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry
D000179:Acrylates; D000588:Amines; D004952:Esters; C480500:N-carboxyethylchitosan ethyl ester; D014867:Water; D002686:Chitin; C040833:ethyl acrylate; D048271:Chitosan