Synthesis and polymerization of N-[4-(cholesteroxycarbonyl)phenyl]itaconimide

Abstract

A new type of optically active N-[4-(cholesteroxy-carbonyl)phenyl]itaconimide (ChPII) was synthesized from itaconic anhydride, aminobenzoic acid and cholesterol. Radical homopolymerizations of ChPII were performed in several solvents at 60°C to give optically active polymers having [α]D = 1.7 to [α]D = −6.2°. Anionic homopolymerizations of ChPII were also carried out. Radical copolymerizations of ChPII(M1) were performed with styrene (ST, M2), and methyl methacrylate (MMA, M2) in toluene at 60°C. From the reslts, the monomer reactivity ratios (r1, r2) and the Alfrey-Price Q, e values were determined as follows: r1 = 0.26, r2 = 0.10, Q1 = 2.17, e1 = 1.11 for the ChPII-ST system; r1 = 0.187, r2 = 0.37, Q1 = 2.55, e1 = 1.01 for the ChPII-MMA system. ChPII polymer and copolymers were still optically active after hydrolysis, which suggests that asymmetric induction into the polymer main chain took place. Chiroptical properties of the polymers and copolymers were investigated.