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Cross-Linked Hydrogels Formed Through Diels-Alder Coupling of Furan- And Maleimide-Modified Poly(methyl Vinyl Ether-Alt-Maleic Acid)

Cross-Linked Hydrogels Formed Through Diels-Alder Coupling of Furan- And Maleimide-Modified Poly(methyl Vinyl Ether-Alt-Maleic Acid)

S Alison Stewart, Matilda Backholm, Nicholas A D Burke, Harald D H Stöver

Langmuir. 2016 Feb 23;32(7):1863-70.

PMID: 26800849

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP25153406	Poly(methyl vinyl ether-alt-maleic acid)		25153-40-6	Price

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