POLY(METHYL METHACRYLATE) CONTAINING PYRROLE MOIETIES IN THE SIDE-CHAINS

Two synthetic routes to copolymers 7 of methyl methacrylate (MMA) with 2-(N-pyrrolyl)ethyl methacrylate (PEMA, 11) are compared. Copolymerization of MMA (4) with 2-bromoethyl methacrylate (BEMA, 3) leads to a precursor copolymer 5. The reactivity ratios are close to unity (r(MMA) = 0,90, r(BEMA) = 0,92). The polymer-analogous reaction of 5 with N-pyrrolylpotassium (6) runs to 99% conversion of the BEMA units. The synthesis of PEMA (11) is presented. The reactivity ratios of copolymerization of this monomer (11) with MMA (4) are determined to r(MMA) = 1,05 and r(PEMA) = 1,65. Copolymers 7 are further characterized by H-1 nuclear magnetic resonance, infrared spectroscopy, gel-permeation chromatography and differential scanning calorimetry.