화학공학소재연구정보센터
Journal of Polymer Science Part A: Polymer Chemistry, Vol.35, No.4, 741-746, 1997
Polymerization of Meta-Naphthoquinone Methide - 3,4-Benzo-6-Methylenebicyclo(3.1.0)Hex-3-Ene-2-One
Polymerization behavior of meta-naphthoquinone methide, 3,4-benzo-6-methylenebicyclo [3.1.0] hex-3-ene-2-one (1), was studied. Radical initiator 2,2’-azobis( isobutyronitrile) (AIBN) induced polymerization of 1, but ionic initiators potassium tert-butoxide, butyllithium, and boron trifluoride etherate did not. Polymerization of 1 proceeded via ring-opening and aromatization to give a polymer with head-to-tail monomer unit placement. Compound 1 copolymerized with methyl methacrylate (MMA) in the presence of AIBN to obtain the monomer reactivity ratios r(1)(1) = 0.28 +/- 0.07 and r(2)(MMA) = 0.39 +/- 0.02 at 60 degrees C and Q and e values of Q = 1.04 and e = -1.03, indicating that 1 is a conjugative and electron-donating monomer. Ring-opening and aromatization of I also took place in the copolymerization.