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Article Dans Une Revue Journal of polymer science. Part A-1, Polymer chemistry Année : 2014

Synthesis of Water-Soluble Allyl-Functionalized Oligochitosan and Its Modification by Thiol-Ene Addition in Water

Résumé

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 x-functional mercaptans, using 4,40-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.

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Dates et versions

hal-00910887 , version 1 (28-11-2013)

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Nicolas Illy, Ghislain David, Mike Robitzer, Rémi Auvergne, Sylvain Caillol. Synthesis of Water-Soluble Allyl-Functionalized Oligochitosan and Its Modification by Thiol-Ene Addition in Water. Journal of polymer science. Part A-1, Polymer chemistry, 2014, 52, pp.39-48. ⟨10.1002/pola.26967⟩. ⟨hal-00910887⟩
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