SYNTHESIS AND POLYMERIZATION OF N-(CHOLESTEROXYCARBONYLMETHYL)MALEIMIDE

A new type of optically active N-(cholesteroxycarbonylmethyl)maleimide (ChMI) was synthesized from maleic anhydride, glycine and cholesterol. Radical homopolymerizations of ChMI were performed at 70-degrees-C for 24 h to give optically active polymers having [alpha]D = -25.7 to -34.2-degrees. Radical copolymerizations of ChMI (M1) were performed with styrene (ST, M2), methyl methacrylate (MMA, M2) in benzene at 70-degrees-C. From the results, the monomer reactivity ratios (r1, r2) and Alfrey-Price Q, e values were determined as follows: r1 = 0.090, r2 = 0.082, Q1 = 2.07, e1 = 1.42 for the ChMI-ST system; r1 = 0.13, r2 = 1.22, Q1 = 1.04, e1 = 1.76 for the ChMI-MMA system. Anionic homopolymerizations of ChMI were also carried out. Chiroptical properties of the polymers and copolymers were investigated.