SYNTHESIS AND POLYMERIZATION OF N-[4-(CHOLESTEROXYCARBONYL)PHENYL]MALEIMIDE

A new type of optically active N-[4-(cholesteroxycarbonyl)phenyl]maleimide (ChPMI) was synthesized from maleic anhydride, aminobenzoic acid and cholesterol. Radical homopolymerizations of ChPMI were performed in several solvents at 70-degrees-C to give optically active polymers having [alpha]D = 2.3 to 41.1-degrees. Radical copolymerizations of ChPMI (M1) were performed with styrene (ST, M2) and methyl methacrylate (MMA, M2) in toluene at 70-degrees-C. From the results, the monomer reactivity ratios (r1, r2) and the Alfrey-Price Q, e values were determined as follows: r1 = 0.080, r2 = 0.020, Q1 = 6.57, e1 = 1.74 for the ChPMI-ST system; r1 = 0.11, r2 = 0.80, Q1 = 1.73, e1 = 1.96 for the ChPMI-MMA system. Anionic homopolymerizations of ChPMI were also carried out. Chiroptical properties of the polymers and copolymers were investigated.