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Synthesis and application of novel optically active maleimide polymers with thermostability

Research Project

Project/Area Number 08651054
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionYAMAGUCHI UNIVERSITY

Principal Investigator

OISHI Tsutomu  Yamaguchi University, Faculty of Engineering, Professor, 工学部, 教授 (30091169)

Co-Investigator(Kenkyū-buntansha) TSUTSUMI Hiromori  Yamaguchi University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (90211383)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1997: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1996: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsOptically active polymer / N-Substituted Maleimide / Radical Polmerization / Asymmetric Anionic Polymerization / Monomer Reactivity Ratios / Q and e Values / Asymmetric Induction / Cirular Dichoism / 不斉アニオン重合
Research Abstract

New types of maleimides having methylbenzyl, L-menthyl and amino-acid residual group were synthesized and homopolymerized and copolymerized with stirene and methyl methacrylate. Optical activity of the polymers and copolymers were investigated by circular dichroism and specific rotation measurements. Asymmetric induction took place to the main chain of the polymer and copolymer. Asymmetric anionic polymerizations of optically inactive N-substituted maleimide (N-substituent : cyclohexyl, phenyl) were performed with organometal - chiral ligands to obtain the optically active polymers having + 117 to -155 deg.of specific rotation, which were the highest in the values resported previously. The optical activity of the polymers was attributed to the different content between (S,S) and (R,R) absolute configuration by the threo-diisotactic structures in the main chain. It is considered that the (+) -polymer has more (S,S) absolute configuration than (R,R) and the (-) -polymer has more (R,R) absolute configuration than (S,S), judging from the exciton chirality method and the model compounds. The asymmetric polymerizations of the maleimides having bulky group in the N-substituents such as triphenylmethyl, diphenylmethyl and fluorenyl were also carried out with organometal-chiral ligand to give optically active polymers. The polymers were applied for optical resolution reagents because the polymers have relatively higher specific rotation.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of optically active itaconamate bearing an (R)- -methylbenzyl group" Polymer. 37・24. 5513-5520 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of maleimide containing an L-menthyl group" Polymer. 38・6. 1461-1469 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kenjiro Onimura: "Asymmetric polymerization of N-substituted maleimides with organolithium - bisoxazolines complex" Polymer Bulletin. 39. 437-444 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 大石 勉: "N-マレオイル-L-フェニルアラニンシクロヘキシルエステルの不斉アニオン重合" 高分子論文集. 54・12. 914-922 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of N-substituted malemides based on L-alanine ester" Polymer. (印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi: "Synthesis and Thermostabilities of N-[4-(N′-Substituted Aminocarbonyl) phyenyl] maleimide Polymers" J.Polym. Sci., Part A : Polym.Chem.(印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi, Tetsuji Kawamoto and Hiromori Tsutsumi: "Synthesis and polymerization of optically active itaconamate bearing an (R) -alpha-methylbenzyl group" Polymer. 37 (24). 5513-5520 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi, Kenso Kagawa and Haruo Nagata: "Synthesis and polymerization of maleimide containing an L-methyl group" Polymer. 38 (6). 1461-1469 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Kenjiro Onimura, Hiromori Tsutsumi and Tsutomu Oishi: "Asymmetric polymerization of N-substituted maleimides with organolithium-bisoxazolines complex" Polymer Bulletin. 39. 437-444 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi, Katsuyuki Fujii, Kenjiro Onimura and Hiromori Tsutsumi: "Asymmetric anionic polymerizations of N-maleoyl-L-phenylalanine cyclohexyl ester" Kobunshi Ronbunshu. 54 (12). 914-922 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi, Haruo Nagata and Hiromori Tsutsumi: "Synthesis and polymerization of N-substituted maleimides based on L-alanine ester" Polymer. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi, Kazuki Sase and Hiromori Tsutsumi: "Synthesis and Thermostabilities of N-[4- (N'-Substituted Aminocarbonyl) phenyl] maleimide Polymers" J.Polym.Sci., Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of optically active itaconamate bearing an(R)-α-methylbenzy1 group" Polymer. 37・24. 5513-5520 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of maleimide containing an L-methyl group" Polymer. 38・6. 1461-1469 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Kenjiro Onimura: "Asymmetric polymerization of N-substituted maleimides with organolithium-bisoxazolines complex" Polymer Bulletin. 39. 437-444 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 大石 勉: "N・レオイル・L・フェニルアラニンシクロヘキシルエステルの不斉アニオン重合" 高分子論文集. 54・12. 914-922 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tsutomu Oishi: "Synthesis and polymerization of N-substituted maleimides based on L-alanine ester" Polymer. (印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Tsutomu Oishi: "Syntheses and Thermostabilities of N-[4-(N'-substituted Aminocarbony1)pheny1]maleimide Polymers" J.Polym.Sci.,Part A : Polym.Chem.(印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Tsutomu Oishi: "Sythesis and polymerzation of optically active itaconamate bearing an(R)-α-methlbenzyl group" Polymer. 37・24. 5513-5520 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Tsutomu Oishi: "Sythesis and polymerzation of maleimide containing an L-menthyl group" Polymer. 38・6. 1461-1469 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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