Synthesis and Polymerization of Optically Active N-[4-N′-(α-Methylbenzyl)aminocarbonylphenyl] itaconimide

Abstract

A new type of optically active N-[4-N′-(α-methylbenzyl)aminocarbonylphenyl]-itaconimide (MBPI) was synthesized from itaconic anhydride, p-aminobenzoic acid, and (R)-α-methylbenzylamine. The radical homopolymerization of MBPI was performed in tetrahydrofuran (THF) at 60—130°C for 22 h to give optically active polymers having [α]D25=−46.6 to −51.8°. Anionic polymerizations of MBPI with n-butyllithium in THF and N,N-dimethyl-formamide were performed. But the yields were quite small. Radical copolymerizations of MBPI (M1) were performed with styrene (ST, M2), methyl methacrylate (MMA, M2), or indene (ID, M2) in THF at 70°C. Monomer reactivity ratios (r1, r2) and Alfrey–Price Q–e values were calculated. Chiroptical properties of the polymers and copolymers were also investigated.