Synthesis, Characterization, and Cyclopolymerization of a Functional Non-Symmetric Divinyl Monomer

Bekir Dizman
Lon J. Mathias, University of Southern Mississippi


A non-symmetric divinyl monomer with terminal carboxylic acid functionality was readily synthesized from the reaction of ethyl alpha-hydroxymethylacrylate (EHMA) with maleic anhydride. The new monomer (EHMA-MA) was homopolymerized in both bulk and ethyl acetate using AIBN as an initiator to give cyclopolymers. The synthesis of the monomer and cyclopolymers were followed by C-13 NMR, H-1 NMR, and FTIR. H-1 NMR was also utilized to obtain the degree of cyclization of the polymers, which were found to be 95% or higher in all cases. The molecular weights of the cyclopolymers were around 40-60,000 g/mol as estimated by SEC. The cyclopolymers were thermally stable up to 150 degrees C. Although the cyclopolymers obtained were not water-soluble; they were soluble in aqueous 1 M NaOH solution. In addition to the carboxylic acid functionality present, the cyclopolymers also had an ethyl ester and a lactone moiety. These functional groups were reacted with hexylamine to obtain a polymer with imide and amide moieties. (c) 2007 Elsevier Ltd. All rights reserved.