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Synthesis of water‐soluble allyl‐functionalized oligochitosan and its modification by thiol–ene addition in water
Authors:Nicolas Illy  Mike Robitzer  Rémi Auvergne  Sylvain Caillol  Ghislain David  Bernard Boutevin
Institution:Institut Charles Gerhardt Montpellier UMR5253 CNRS‐UM2‐ENSCM‐UM1, , France
Abstract:A novel, straightforward and versatile chemical pathway has been studied to functionalize water‐soluble chitosan oligomers. This metal‐free methodology is based on the epoxy‐amine reaction of the allyl glycidyl ether with chitosan, followed by thiol‐ene radical coupling reaction of ω‐functional mercaptans, using 4,4′‐Azobis(4‐cyanovaleric acid) as a free radical initiator. Both reactions were entirely carried out in water. In a preliminary step, chitosan depolymerization was carried out using H2O2 in an acetic medium under 100 W microwave irradiation, optimizing the yield of water‐soluble oligomers. Functionalization by six different thiols bearing alcohol, carboxylic acid, ester, and amino groups was then performed, leading to a range of functional oligochitosans with different grafting efficiencies. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014 , 52, 39–48
Keywords:allylated chitosan  chitosan  oligomers  radical polymerization  synthesis  thiol‐ene addition  water‐soluble polymers
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