New Poly(ester amide)s from Alkyl 2-(carboethoxyhydroxymethyl)acrylates

Lon J. Mathias, University of Southern Mississippi

Originally published in Journal of Polymer Science, Part A: Polymer Chemistry, Volume 46, Issue 10, 15 May 2008, Pages 3182-3192

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The synthesis of alkyl 2-(carboethoxyhydroxymethyl)acrylates via the Bayllis-Hillmann reaction pathway is described. These compounds are found to be poor monomers when involved in free radical polymerizations but present an extremely high reactivity upon Michael addition with primary amines leading to a simple, mild and efficient route to the preparation of new multifunctional heterocycles and polymers with potential applications in biodegradable coatings. Real-time NMR spectroscopy permitted monitoring the extent of the reaction sequence and determining the conversion profile of reactants and Michael adduct intermediate. Poly(ester amide)s derived from diamine and hexane bis-2-(carboethoxyhydroxymethyl)acrylate were synthesized at room temperature by means of a very efficient Michael addition/cyclization polymerization. These polymers display excellent adhesion to metal, glass, and paper substrates and interesting hydrolytic susceptibility. © 2008 Wiley Periodicals, Inc.