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 ¹H nuclear magnetic resonance, infrared spectroscopy, gel-permeation chromatography and differential scanning calorimetry.