Title

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

Document Type

Article

Publication Date

1-1-2008

Department

Chemistry and Biochemistry

Abstract

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.

Publication Title

Journal of Polymer Science, Part A: Polymer Chemistry

Volume

46

Issue

10

First Page

3182

Last Page

3192