Synthesis, polymerization and copolymerization of N-(2-acryloyloxyethyl)phthalimide

Abstract

The present paper reports the synthesis and free-radical polymerization of N-(2-acryloyloxyethyl)phthalimide (A) and its copolymerization with methyl methacrylate (M). This acrylic monomer was prepared in fairly good yield according to a synthetic scheme that includes two steps. The purified acrylic derivative was polymerized in dimethylformamide solution at 60°C, using azobisisobutyronitrile as free-radical initiator. The kinetic behaviour indicates that this monomer presents a rather high polymerization rate, with a value of k p k 1 2 t = 1.36 l 1 2 mol −1 2 s −1 2 . Copolymerization reactions were carried out in the same experimental conditions and the reactivity ratios were determined by the application of the Kelen-Tüdös and non-linear least-squares methods. The values of reactivity ratios calculated by the linearization method were r A = 0.29 ± 0.02 and r M = 3.02 ± 0.32, whereas the application of the non-linear least-squares method gave values of r A = 0.30 and r M = 3.07. From these values the corresponding Q and e parameters were calculated, giving values of Q = 0.27 and e = 0.71.