SYNTHESIS AND POLYMERIZATION OF N-(L-MENTHYLCARBOXYLATOMETHYL)MALEIMIDE

A new type of optically active N-(L-menthylcarboxylatomethyl) maleimide (MGMI) was synthesized from maleic anhydride, glycine, and L-menthol. Radical homopolymerization of MGMI was performed at 50-degrees-C for 24 h to give optically active polymer having [alpha]D = -57-degrees. Radical copolymerizations of MGMI (M1) were performed with styrene (ST, M2), methyl methacrylate (MMA, M2) in benzene at 50-degrees-C. From the results, the monomer reactivity ratios (r1, r2) and the Alfrey-Price Q, e values were determined as follows: r1 = 0.16, r2 = 0.006 for the MGMI-ST system; r1 = 0.15, r2 = 1.65 for the MGMI-MMA system, and Q1 = 0.72, e1 = 1.59 calculated from the MGMI-MMA system. Anionic homopolymerizations of MGMI were also carried out. Chiroptical properties of the polymers were investigated.