SYNTHESIS AND POLYMERIZATION OF N-[4-N'-(ALPHA-METHYLBENZYL)AMINOCARBONYLPHENYL]MALEIMIDE

A novel type of optically active N-[4-N'-(alpha-methylbenzyl)aminocarbonylphenyl] maleimide [ (R)-MBCP ] was synthesized from maleic anhydride, p -aminobenzoic acid, and (R)-methylbenzylamine. Radical homopolymerization of (R) -MBCP was performed in tetrahydrofuran (THF) at 50 and 70-degrees-C for 24 h to give optically active polymers having [alpha]D25 = -141-degrees and -129-degrees, respectively. Anionic polymerization of (R) -MBCP with n-butyllithium in THF and NN-dimethylformamide gave an optically active polymer having -78 to -81-degrees of [alpha]D25. Radical copolymerizations of (R) -MBCP (M1) were performed with styrene (ST, M2) and methyl methacrylate (MMA, M2) in THF at 50-degrees-C. The monomer reactivity ratios (r1, r2) and the Alfrey-Price Q-e values were determined as follows: r1 = 0.009, r2 = 0.091, Q1 = 1.30, e1 = 1.87 in the (R)-MBCP-ST; r1 = 0.27, r2 = 1.21, Q1 = 0.93, e1 = 1.46 in the (R) -MBCP-MMA system. Chiroptical properties of the polymers were also investigated.