Synthesis, characterization, and cyclopolymerization of a functional non-symmetric divinyl monomer

A non-symmetric divinyl monomer with terminal carboxylic acid functionality was readily synthesized from the reaction of ethyl α-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 13C NMR, 1H NMR, and FTIR. 1H 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 °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.