Synthesis and Polymerization of Optically Active Mono-I-Menthyl Itaconate |
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| Authors: | Tsutomu Oishi Minoru Fujimoto |
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| Affiliation: | Department of Industrial Chemistry, Technical College , Yamaguchi University , 2557 Tokiwadai, Ube, Yamaguchi, 755, Japan |
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| Abstract: | Optically active mono-l-menthyl itaconate (MMI) was prepared from ita-conic acid and l-menthol. MMI was polymerized in bulk at 80°C to give a chiral homopolymer having -49.5° specific rotation. MMI (M1 was copolymerized with styrene (ST, M2), methyl methacrylate (MMA, M2), and N-cyclohexylmaleimide (CHMI, M2) by using 2,2′-azobisisobutyronitrile (AIBN) as the radical initiator and benzene as the polymerization solvent at 50°C. The monomer reactivity ratios (r1, r2) and Alfrey-Price Q, e values were determined to be r1 = 0.28, r2 = 0.32, Q1 = 0.90, and e1 = 0.75 in MMI-ST; r1 = 0.09 and r2 = 0.51 in MMI-MMA; and r1 = 0.78 and r2 = 0.39 in MMI-CHMI. The chiroptical properties of the polymers were investigated. |
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