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Living Radical Polymerization using Organic Selenium Compounds

Research Project

Project/Area Number 10650865
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionNagoya Institute of Technology

Principal Investigator

YUKI Yasuo  Nagoya Institute of Technology, Faculty of Engineering, Professor, 工学部, 教授 (20024292)

Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2000: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1999: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1998: ¥2,100,000 (Direct Cost: ¥2,100,000)
KeywordsOrganic Selenium Compound / Living Radical Polymerization / Block Copolymer / End Functional Polymer / Macromonomer / Graft Copolymer / Hyperbranched Polymer / Photoiniferter / トリブロック共重合体 / p-(フェニルセレノメチル)スチレン / ジフェニルジセレニド / ベンジルフェニルセレニド / 片末端官能性高分子 / クラフト共重合体 / ジフェニルジテルリド / 二官能性イニファタ / 高分子光イニファタ / 両末端フェニルセレノ基 / テレケリック高分子 / ジおよびトリブロック共重合体
Research Abstract

Organic selenium compounds are very useful in organic chemistry. We found that the organic selenium compounds (benzyl phenyl senide or diphenyl diselenide) works as a photoiniferter in radical polymerization of styrene and methyl methacrylate.
The carbon-selenium bond of benzyl phenyl selenide undergoes homolytic cleavage on photoirradiation to afford phenylseleno and benzyl radicals, and styrene monomer insert to these radicals to afford polymer with higher molecular weight. The resulting polystyrene having phenylseleno group at theω-end works also as a polymeric photoiniferter, and can apply to the synthesis of block copolymer. Further, the phenylseleno group at theω-end is eliminated by hydrogen peroxide to give carbon-carbon double bond and, followed the resulting polystyrene is converted to epoxy terminated polystyrene, and then macromonomer.
1, 4-Bis (p-tert-butylphenylselenomethyl) benzene was used as a bifunctional photoiniferter for the polymerization of styrene and methyl methacrylate. Photoirradiation of telechelic polystyrene having phenylseleno groups at both ends as polymeric photoiniferter in the presence of methyl methacrylarte afforded effectively corresponding to the ABA type triblock copolymers.
p-Phenylselenomethylstyrene was synthesized as a novel-selenium-containing vinyl monomer and polymerized with azobisisobutyronitrile to afford corresponding homopolymer. Photoirradiation of the copolymer of this monomer and styrene as a polymeric photoiniferter in the presence of methyl methacrylarte effectively afforded a graft copolymer. On the other hand, the homopolymerization of this monomer under UV irradiation gave a hyperbranched polystyrene.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 results)

  • [Publications] T.S.Kwon,S.Kondo,H.Kunisada,and Y.Yuki: "Synthesis of Polystyrene and Poly (methyl methacrylate) Each with a Phenyl Seleno Group at Terminal Chain End by Radical Polymerization in the Presence of Benzyl Phenyl Selenide as a Photoiniferter"Polymer Journal.. 30(7). 559-565 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,S.Kumazawa,S.Kondo,K.Takagi,H.Kunisada,and Y.Yuki: "Synthesis of Telechelic Polystyrene by Radical Polymerization using 1,4-Bis (p-tert-butylselenomethyl) benzene as a Photoiniferter"J.Macromol.Sci.Pure Appl.Chem.. A35(12). 1895-1913 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,S.Kondo,H.kunisads,and Y.Yuki: "Synthesis of Polystyrenes with Arylseleno Groups at the Terminal Bond, by the Free Radical Polymerization of Styrene in the Presence of Diaryl Diselenides, and Their Conversion to End Functional Polymers"European Polymer Journal,. 35. 727-737 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,H.Ochiai,S.Kondo,K.Takagi,H.Kunisada,and Y.Yuki: "Radical Polymerization of p-Substituted Styrenes with Benzyl Phenyl Selenide as Photoiniferter"Polymer Journal.. 31(5). 411-417 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,S.Kondo,K.Takagi,H.Kunisada,and Y.Yuki: "Synthesis and Radical Polymerization of p-Phenylselenomethylstyrene and Applications to Graft Copolymers"Polymer Journal,. 31(6). 483-487 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Takagi,A.Soyano,T.S.Kwon,H.Kunisada,and Y.Yuki: "Controlled Radical Polymerization of Styrene Utilizing Excellent Radical Capturing Ability of Diphenyl Ditelluride"Polymer Bulletin. 43(2-3). 143-150 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,K.Takagi,H.Kunisada,and Y.Yuki: "Synthesis of Macromonomer Using End Functional Polystyrene Prepared from p-Methoxybenzyl p-Trimethylsilylphenyl Selenide as a Photoiniferter"J.Macromol.sci.Pure Appl.Chem.. A37(11). 1461-1473 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Takagi,Y.Nishikawa,T.S.Kwon,H.Kunisada,and Y.Yuki: "Synthesis of Branched Polystyrene by Photopolymerization of Selenium-Containing styrene Monomer"Polymer Journal. 32(11). 970-973 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,K.Suzuki,K.Takagi,H.Kunisada,and Y.Yuki: "Radical Polymerization of Methyl Methacrylate with Diphenyl Diselenide under Thermal or Photoirradiational Conditions"J.Macromol.Sci.Pure Appl.Chem.. A38(5&6). 591-604 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,K.Takagi,H.Kunisada,and Y.Yuki: "Synthesisi of ABA Type Triblock Copolymers by Radical Polymerization with 1,4-Bis (p-tert-butylphenylselenomethyl) benzene as a Photoiniferter"J.Macromol.Sci.Pure Appl.Chem.. A38(5&6). 605-626 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, S.Kondo, H.Kunisada, and Y.Yuki: "Synthesis of Polystyrene and Poly (methyl methacrylate) Each with a Phenyl Seleno Group at Terminal Chain End by Radical Polymerization in the Presence of Benzyl Phenyl Selenide as a Photoiniferter"Polymer Journal. 30 (7). 559-565 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, S.Kumazawa, S.Kondo, K.Takagi, H.Kunisada, and Y.Yuki: "Synthesis of Telechelic Polystyrene by Radical Polymerization using 1, 4-Bis (p-tert-butylselenomethyl) benzene as a Photoiniferter"J.Macromol. Sci. Pure Appl. Chem.. A35 (12). 1895-1913 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, S.Kondo, H.Kunisada, and Y.Yuki: "Synthesis of Polystyrenes with Arylseleno Groups at the Radical Polymerization of Terminal Bond, by the Free Styrene in the Presence of Diaryl Diselenides, and Their Conversion to End Functional Polymers"European Polymer Journal. 35. 727-737 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, H.Ochiai, S.Kondo, K.Takagi, H.Kunisada, and Y.Yuki: "Radical Polymerization of p-Substituted Styrenes with Benzyl Phenyl Selenide as Photoiniferter"Polymer Journal. 31 (5). 411-417 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, S.Kondo, K.Takagi, H.Kunisada, and Y.Yuki: "Synthesis and Radical Polymerization of p-Phenylselenomethylstyrene and Applications to Graft Copolymers"Polymer Journal. 31 (6). 483-487 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Takagi, A.Soyano, T.S.Kwon, H.Kunisada, and Y.Yuki: "Controlled Radical Polymerization of Styrene Utilizing Excellent Radical Capturing Ability of Diphenyl Ditelluride"Polymer Bulletin. 43 (2-3). 143-150 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, K.Takagi, H.Kunisada, and Y.Yuki: "Synthesis of Macromonomer Using End Functional Polystyrene Prepared from p-Methoxybenzyl p-Trimethylsilylphenyl Selenide as a Photoiniferter"J.Macromol. Sci. Pure Appl. Chem.. A37 (11). 1461-1473 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] K.Takagi, Y.Nishikawa, , T.S.Kwon, H.Kunisada, and Y.Yuki: "Synthesis of Branched Polystyrene by Photopolymerization of Selenium-Containing Styrene Monomer"Polymer Journal. 32 (11). 970-973 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, K.Suzuki, K.Takagi, H.Kunisada, and Y.Yuki: "Radical Polymerization of Methyl Methacrylate with Diphenyl Diselenide under Therrnal or Photoirradiational Conditions"J.Macromol. Sci. Pure Appl. Chem.. A38 (5&6). 591-604 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon, K.Takagi, H.Kunisada, and Y.Yuki: "Synthesisi of ABA Type Triblock Copolymers by Radical Polymerization with 1, 4-Bis ( p-tert-butylphenylselenomethyl) benzene as a Photoiniferter"J.Macromol. Sci. Pure Appl. Chem.. A38 (5&6). 605-626 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.S.Kwon,K.Takagi,H,Kunisada,Y.Yuki: "Synthesis of Macromonomer using End Functional Polystyrene Prepared from p-Methoxybenzyl p-Trimethylsilylphenyl Selenide as a photoiniferter"J.M.S.-Pure Appl.Chem.. A37(11). 1461-1473 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Takagi,Y.Nishikawa,T.S.Kwon,H.Kunisada,Y.Yuki: "Synthesis of Branched Polystyrene by Photopolymerization of Selenium-Containing Styrene Monomer"Polymer Journal. 52(11). 970-973 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.S.Kwon,K.Takagi,H.Kunisada,Y.Yuki: "Synthesisi of ABA Type Triblock Copolymers by Radical Polymerization with 1,4-Bis (p-tert-butylphenylselenomethyl) benzene as a Photoiniferter"J.M.S.-Pure Appl.Chem. A38(5)(In press). (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.S.Kwon,S.Kondo,H.Kunisada,Y.Yuki: "Synthesis of Ploystyrenes with Arylseleno Groups at the Terminal Bond,by the Free Radical Polymerization of Styrene in the Presence of Diaryl Diselenides,and Their Conversion to End Functional Polymers"European Polymer Journal. 35巻4号. 727-737 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.S.Kwon,H.Ochiai,S.Kondo,K.Takagi,H.Kunisada,Y.Yuki: "Radical Polymerization of p-Substituted Styrenes with Benzyl Phenyl Selnide as a Photoiniferter"Polymer Journal. 31巻5号. 411-417 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.S.Kwon,S.Kondo,K.Takagi,H.Kunisada,Y.Yuki: "Synthesis and Radical Polymerization of p-Phenylselenosyurene and Application to Graft Copolymer"Polymer Journal. 31巻6号. 483-487 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Takagi,A.Soyano,T.S.Kwon,H.Kunisada,Y.Yuki: "Controlled Radical Polymerization of Styrene Utilizing Exellent Radical Capturing Ability of Diphenyl Ditelluride"Polymer Bulletin. 43巻. 143-150 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T.S.Kwon,S.Kumazawa,T.Yokoi S.Kondo,H.Kunisada,Y.Yuki: "Living Radical Polymerization of Styrene with Diphenyl Diselenide as a Photoini-ferter.Synthesis of Polystyrene with Carbon-Carbon Double Bonds at Both Chain Ends" J.Macromol.Sci.Pure Appl.Chem.A34巻9号. 1553-1567 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.S.Kwon,S.Kondo,H.Kunisada,Y.Yuki: "Synthesis of Polystyrene and Poly(methyl methacrylate)Each with a Phenyl Seleno Group at Terminal Chain End by Radical Polymerization in the Presence of Benzyl Phenyl Selonide as a Photoiniferter" Polymer Journal. 30巻7号. 559-565 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.S.Kwon,S.Kumazawa,S.Kondo,K.Takagi,H.Kunisada,Y.Yuki: "Synthesis of Telechelic Polystyrene by Radical Polymerization using 1,4-Bis(p-tert-butylphenylselenomethyl)benzene as a Photoiniferter" J.Macromol.Sci.Pure Appl.Chem.A35巻12号. 1895-1913 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.S.Kwon,S.Kondo,H.Kunisada,Y.Yuki: "Synthesis of Polystyrenes with Arylseleno Groups at the Terminal Bond,by the Free Radical Polymerization of Styrene in the Presence of Diaryl Diselenides,and Their Conversion to End Functional Polymers" European Polymer Journal. (印刷中).

    • Related Report
      1998 Annual Research Report
  • [Publications] T.S.Kwon,H.Ochiai,S.Kondo,K.Takagi,H.Kunisada,Y.Yuki: "Radical Polymerization of p-Substituted Styrenes with Benzyl Phenyl Selnide as a Photoiniferter" Polymer Journal. 31巻6号(印刷中).

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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