Cross-Linked Hydrogels Formed through Diels-Alder Coupling of Furan- and Maleimide-Modified Poly(methyl vinyl ether-alt-maleic acid)

Langmuir : the ACS Journal of Surfaces and Colloids
S Alison StewartHarald D H Stöver

Abstract

The Diels-Alder [4 + 2] cycloaddition between furan- and maleimide-functional polyanions was used to form cross-linked synthetic polymer hydrogels. Poly(methyl vinyl ether-alt-maleic anhydride) was reacted with furfurylamine or N-(2-aminoethyl)maleimide in acetonitrile to form pairs of furan- and maleimide-functionalized poly(methyl vinyl ether-alt-maleic acid)s. Mixtures of these mutually reactive polyanions in water gelled within 15 min to 18 h, depending on degree of functionalization and polymer concentrations. Solution and magic-angle spinning (1)H NMR were used to confirm the formation of the Diels-Alder adduct, to analyze competing hydrolytic side reactions, and demonstrate postgelation functionalization. The effect of the degree of furan and maleimide functionalization, polymer concentration, pH, and calcium ion concentration, on gelation time, gel mechanical properties, and equilibrium swelling, are described. Release of dextran as a model drug was studied using fluorescence spectroscopy, as a function of gel composition and calcium treatment.

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Citations

Dec 30, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yavuz Oz, Amitav Sanyal
Oct 28, 2017·Nature Communications·Shuhei NodaAkihiko Kondo
Dec 1, 2017·Polymer International·Ying HaoXinqiao Jia
May 16, 2020·Chemistry of Materials : a Publication of the American Chemical Society·Christopher M Madl, Sarah C Heilshorn

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