Radical Polymerization of N-(2-Alkoxycarbonylphenyl)Maleimides

Abstract Radical polymerization of N-(2-methoxycarbonylphenyl)maleimide (2MCPhMI), N-(2-ethoxycarbonylphenyl)maleimide (2ECPhMI), and N-(2-n-butoxycarbonylphenyl)maleimide (2BCPhMI) was carried out in benzene at 60°C. The polymerization reactivity was examined as well as the solubility and the thermal properties of the resulting polymers. The effects of the alkyl groups in the 2-substituent on the reactivity and properties were discussed. Furthermore, the polymerization of 2BCPhMI was investigated kinetically in detail. It was revealed that the polymerization rate (R p) is represented by R p = k[2BCPhMI]0.84. [MAIB]0.88, where MAIB is dimethyl 2,2′-azobis(isobutyrate). The propagation and termination rate constants were determined for these polymerization systems by ESR method. The large reaction order with respect to the initiator concentration was interpreted by the termination rate constant depending on the initiator concentration.

[1]  A. Matsumoto,et al.  Alternating copolymerization of N‐(alkyl‐substituted phenyl)maleimides with isobutene and thermal properties of the resulting copolymers , 1996 .

[2]  A. Matsumoto,et al.  Evaluation of the Chain-Length Dependence of the Termination Rate Constant during Radical Polymerization of a Methacrylic Ester , 1994 .

[3]  A. Matsumoto,et al.  Detailed kinetic analysis of the radical polymerization of trans-4-tert-butylcyclohexyl methacrylate in benzene based on the rate constants determined by electron spin resonance spectroscopy , 1994 .

[4]  A. Matsumoto,et al.  Effects of the substituents on radical polymerization kinetics of n-(alkyl-substituted phenyl)maleimides initiated with dimethyl 2,2′-azobisisobutyrate , 1993 .

[5]  A. Matsumoto,et al.  Synthesis and thermal properties of poly(cycloalkyl methacrylate)s bearing bridged‐ and fused‐ring structures , 1993 .

[6]  A. Matsumoto,et al.  Propagation and Termination Rate Constants of N-tert-Alkyl- and N-Trialkylsilylmaleimides in Radical Polymerization Initiated with 2,2′-Azobisisobutyronitrile , 1993 .

[7]  A. Matsumoto,et al.  Radical polymerization of n-(ethoxycarbonylphenyl)maleimides and characterization of the polymers , 1992 .

[8]  T. Oishi,et al.  Synthesis and polymerization of N‐[4‐N′‐ (α‐methylbenzyl)aminocarbonylphenyl]maleimide , 1992 .

[9]  A. Matsumoto,et al.  Steric effect of alkyl substituents on propagation rate constants of N-(2,6-dialkylphenyl)maleimides in radical polymerization , 1992 .

[10]  T. Oishi,et al.  Polymerization and Copolymerization of N-(4-Carboxyphenyl)maleimide , 1991 .

[11]  M. Kubo,et al.  Polymerization thermodynamics of N-phenylmaleimide and its copolymerizations with styrene and phenyl vinyl sulfide , 1991 .

[12]  A. Matsumoto,et al.  Synthesis of high molecular weight poly(dialkyl fumarate)s bearing n-alkyl side chains from poly(di-tert-butyl fumarate) via olefin elimination and reesterification in a one-pot , 1991 .

[13]  A. Matsumoto,et al.  Synthesis, Thermal Properties, and Gas Permeability of Poly(N-n-alkylmaleimide)s , 1991 .

[14]  A. Matsumoto,et al.  Radical polymerization of N-(alkyl-substituted phenyl)maleimides: synthesis of thermally stable polymers soluble in nonpolar solvents , 1990 .

[15]  博 相田,et al.  アクリロニトリル, N-フェニルマレイミド, 及びN-p-クロロフェニルマレイミドとa-メチルスチレンのラジカル共重合及び共重合体の熱的性質 , 1990 .

[16]  J. P. Bell,et al.  Thermoplastic matrix composites by aqueous electrocopolymerization onto graphite fibers , 1990 .

[17]  Tsuneyuki Sato,et al.  Kinetic and electron spin resonance studies on the radical polymerization of N-cyclohexylmaleimide in benzene , 1989 .

[18]  博 相田,et al.  N-置換マレイミド及び無水マレイン酸とα-メチルスチレンとの共重合体の熱分解に及ぼすイミド基及び酸無水物基の影響 , 1988 .

[19]  M. Sabaa,et al.  Copolymerization of acrylonitrile with maleamic acid derivatives and with carboxyphenylmaleimide , 1988 .

[20]  M. Kamachi.  ESR studies on radical polymerization , 1987 .

[21]  Shigeki Mori,et al.  Radical high polymerization of di-tert-butyl fumarate and novel synthesis of high molecular weight poly(fumaric acid) from its polymer , 1984 .

[22]  F. Fernández‐Martín,et al.  Relation between structure and thermal transitions in comb‐like polymers, 1. Poly(N‐n‐alkylmaleimide)s , 1983 .

[23]  J. D. L. Campa,et al.  Free-Radical Copolymerizations of N-Phenyl Maleimide , 1977 .

[24]  勉 大石,et al.  N-n-ヘキシル-, N-シクロヘキシル-, N-ベンジル-マレイミドの重合・共重合 , 1976 .

[25]  Y. Nakayama,et al.  Radical and anionic homopolymerization of maleimide and N‐n‐butylmaleimide , 1967 .

[26]  正盛 山田,et al.  〔46〕 不飽和二塩基酸誘導体の合成, 重合に関する研究 , 1967 .