Poly(vinyl alcohol)-Based Hydrogels Formed by “Click Chemistry”

Abstract

Novel poly(vinyl alcohols) (PVA) functionalized with pendant acetylene and azide groups were prepared by carbonyldiimidazole (CDI)-mediated couplings of the amines terminated with functional groups, 1-azido-2-aminoethane, propargylamine, or N-methylpropargylamine, to PVA. Low degrees (1−5%) of PVA modification were required in order to retain solubility in water. Azide-modified PVA and alkyne-modified PVA components were cross-linked by mixing of their solutions together with Cu(I) catalyst, a type of Huisgen's 1,3-dipolar azide−alkyne cycloaddition, recently defined as a powerful “click” chemistry. Reaction of the two different polymers results in a chemoselective coupling between alkynyl and azido functional groups with the multiple formation of triazole cross-links to give hydrogel formation. In another version the PVA-based hydrogels were obtained by cross-linking of alkyne-modified PVA with the telechelic bifunctional poly(ethylene glycol)−diazide cross-linker. The hydrogels prepared by these two met...