The article describes the synthesis and characterization of N-(4-methoxy-3-chlorophenyl) itaconimide (MCPI) and N-(2-methoxy-5-chlorophenyl) itaconimide (OMCPI) obtained by reacting itaconic anhydride with 4-methoxy-3-chloroanisidine and 2-methoxy-5-chloroanisidine, respectively. Structural and thermal characterization of MCPI and OMCPI monomers was done by using H-1 NMR, FTIR, and differential scanning calorimetry (DSC). Copolymerization of MCPI or OMCPI with methyl methacrylate (MMA) in solution was carried out at 60 degrees C using AIBN as an initiator and THF as solvent. Feed compositions having varying mole fractions of MCPI and OMCPI ranging from 0.1 to 0.5 were taken to prepare copolymers. Copolymerizations were terminated at low percentage conversion. Structural characterization of copolymers was done by FTIR, H-1 NMR, and elemental analysis and percent nitrogen content was used to calculate the copolymer composition. The monomer reactivity ratios for MMA-MCPI copolymers were found to be r(1) (MMA) = 0.32 +/- 0.03 and r(2) (MCPI) = 1.54 +/- 0.05 and that for MMA-OMCPI copolymers were r(1) (MMA) = 0.15 +/- 0.02 and r(2) (OMCPl) = 1.23 +/- 0.18. The intrinsic viscosity [71] of the copolymers decreased with increasing mole fraction of MCPI/or OMCPI. The glass transition temperature as determined from DSC scans was found to increase with increasing amounts of OMPCI in copolymers. A significant improvement in the char yield as determined by thermogravimetry was observed upon copolymerization. (c) 2006 Wiley Periodicals, Inc.