Atom-transfer radical copolymerization of furfuryl methacrylate (FMA) and methyl methacrylate (MMA): A thermally-amendable copolymer

Polymers of furfuryl methacrylate (FMA) are interesting materials because of the presence of the furfuryl group as the reactive diene functionality in the pendent group. Copolymers of FMA and MMA were prepared using atom-transfer radical polymerization (ATRP) catalyzed by CuCl, in combination with HMTETA as a ligand at 90 degrees C. It was very difficult to prepare by conventional radical polymerization because of several side reactions involving the reactive diene group. The copolymer composition was calculated using H-1 NMR studies. The reactivity ratios of FMA and MMA (r(1) and r(2)) were determined using the Finemann-Ross and Kelen-Tudos linearization methods. The reactivity ratios obtained were r(1) = 1.56 and r(2) = 0.56. Diels-Alder chemistry was carried out using the reactive diene of the copolymers and a maleimide as the dienophile. Interestingly, the resultant material was observed to be thermoreversible as evidenced by FT-IR spectroscopy and DSC studies.