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Synthesis of Pure and High Molecular-weight Poly(phenylene sulfide) Derivatives and Development of Their Functionality

Research Project

Project/Area Number 16K14010
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionWaseda University

Principal Investigator

Oyaizu Kenichi  早稲田大学, 理工学術院, 教授 (90277822)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords高分子合成 / 高分子構造・物性 / 機能性高分子 / 錯体触媒 / 酸化重合 / エンジニアリングプラスチック / 透明樹脂 / 屈折率
Outline of Final Research Achievements

Polymerization of diphenyl disulfide (PhSSPh) proceeded in the presence of vanadyl complexes to catalyze the oxidation of PhSSPh with oxygen. Because water decomposed the active form of the catalyst, pricy strong acid anhydrides have been regarded as essential. We solved this problem using molten PhSSPh as the monomer, where the eliminated water was removed by evaporation. This led to the establishment of the process to yield highly pure and high molecular-weight PPS. Calculation results suggested the terminal disulfide functionality, based on the comparison of the HOMO levels and the shapes of their lobes. The reaction was expanded to those with many kinds of diaryl disulfides to yield poly(1,4-arylene sulfide)s (PAS), typically for those containing methyl groups at the phenyl ring. The PAS, derived from bis(3,5-dimethylphenyl) disulfide, showed a high glass transition temperature with the capability of wet processing by virtue of the enhanced solubility in common organic solvents.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (23 results)

All 2018 2017 2016

All Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Int'l Joint Research: 5 results)

  • [Journal Article] Diffusion-cooperative Model for Charge Transport by Redox-active Nonconjugated Polymers2018

    • Author(s)
      K. Sato, R. Ichinoi, R. Mizukami, T. Serikawa, Y. Sasaki, J. Lutkenhaus, H. Nishide, K. Oyaizu
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 140 Issue: 3 Pages: 1049-1056

    • DOI

      10.1021/jacs.7b11272

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Poly(diphenanthrenequinone-substituted norbornene) for Long Life and Efficient Lithium Battery Cathodes2018

    • Author(s)
      T. Kawai, S. Nakao, H. Nishide, K. Oyaizu
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 91 Issue: 5 Pages: 721-727

    • DOI

      10.1246/bcsj.20170420

    • NAID

      130006734123

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Highly Crystallized Poly(1,4-phenylene sulfide) via Oxygen-Oxidative Polymerization of Diphenyl Disulfide2017

    • Author(s)
      Aida Fuyuki、Takasu Naoto、Takatori Yohei、Nishide Hiroyuki、Oyaizu Kenichi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 90 Issue: 7 Pages: 843-846

    • DOI

      10.1246/bcsj.20170055

    • NAID

      130005773708

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 高純度ポリフェニレンスルフィドの合成化学2017

    • Author(s)
      小柳津研一
    • Journal Title

      ENEOS Technical Review

      Volume: 59 Pages: 11-14

    • NAID

      40021126812

    • Related Report
      2016 Research-status Report
  • [Journal Article] Enhanced Catalytic Activity of Oxovanadium Complexes in Oxidative Polymerization of Diphenyl Disulfide2016

    • Author(s)
      F. Aida, Y. Takatori, D. Kiyokawa, K. Nagamatsu, K. Oyaizu, H. Nishide
    • Journal Title

      Polym. Chem.

      Volume: 7 Issue: 11 Pages: 2087-2091

    • DOI

      10.1039/c5py01980j

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Emerging Organosulfonium Electrophiles as Unique Reagents for Carbon–Sulfur Bond Formation: Prospects in Synthetic Chemistry of Organosulfur Compounds2016

    • Author(s)
      F. Aida, K. Oyaizu
    • Journal Title

      Chemistry Letters

      Volume: 45 Issue: 2 Pages: 102-109

    • DOI

      10.1246/cl.151035

    • NAID

      130005124741

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 酸化重合による高耐熱性芳香族ポリチオエーテルの合成2018

    • Author(s)
      平井元康, 齋藤聖也, 山﨑智也, 小柳津研一, 西出宏之
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 酸化重合によるエチル置換ポリフェニレンスルフィドの合成とその性質2018

    • Author(s)
      舜, 齋藤聖也, 田中瑶子, 小柳津研一, 西出宏之
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジスルフィドの酸化重合によるメチル置換ポリフェニレンスルフィドの合成とその性質2017

    • Author(s)
      齋藤聖也, 田中瑶子, 山﨑智也, 小柳津研一, 西出宏之
    • Organizer
      日本化学会第97春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 芳香族ジスルフィドの酸化重合による高屈折率ポリマーの合成とその性質2017

    • Author(s)
      田中瑶子, 西出宏之, 小柳津研一
    • Organizer
      第66回高分子学会年次大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and Properties of Alkyl-substituted Poly(phenylene sulfide)s by Oxidative Polymerization of Disulfide2017

    • Author(s)
      T. Yamazaki, Y. Tanaka, S. Saito, K. Oyaizu, H. Nishide
    • Organizer
      IUPAC 17th International Symposium on Macromolecular Complexes (MMC-17)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Optical Properties of Methyl-substituted Poly(phenylene sulfide)s by Oxidative Polymerization2017

    • Author(s)
      S. Saito, Y. Tanaka, T. Yamazaki, K. Oyaizu, H. Nishide
    • Organizer
      IUPAC 17th International Symposium on Macromolecular Complexes (MMC-17)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 高屈折率を示す芳香族ポリチオエーテルの合成とその熱および光学特性2017

    • Author(s)
      田中瑶子, 西出宏之, 小柳津研一
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 酸化重合によるメチル置換ポリフェニレンスルフィドの合成とその光学特性2017

    • Author(s)
      齋藤聖也, 田中瑶子, 山﨑智也, 小柳津研一, 西出宏之
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and Properties of Alkyl-substituted Poly(phenylene sulfide)s by Oxidative Polymerization Using Vanadyl Catalysts2017

    • Author(s)
      T. Yamazaki, Y. Tanaka, S. Saito, K. Oyaizu, H. Nishide
    • Organizer
      The 15th Pacific Polymer Conference (PPC-15)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ジフェニルジスルフィドの酸化重合による高結晶性ポリフェニレンスルフィドの合成2016

    • Author(s)
      髙須直人, 小柳津研一, 西出宏之
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 酸化重合による高屈折率芳香族ポリチオエーテルの合成とその性質2016

    • Author(s)
      田中瑶子, 青木港, 高須直人, 小柳津研一, 西出宏之
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] 酸化重合による高純度ポリ(アリーレンスルフィド)の合成と性質2016

    • Author(s)
      青木港, 小柳津研一, 西出宏之
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] バナジル触媒を用いた酸化重合によるメチル置換ポリフェニレンスルフィドの合成と熱的性質2016

    • Author(s)
      山﨑智也, 青木港, 小柳津研一, 西出宏之
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and Properties of High Refractive Index Polymers by Oxidative Polymerization of Alkyl-substituted Diphenyl Disulfides2016

    • Author(s)
      Y. Tanaka, M. Aoki, N. Takasu, K. Oyaizu, H. Nishide
    • Organizer
      The 11th SPSJ International Polymer Conference (IPC 2016)
    • Place of Presentation
      東京
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ジスルフィドの酸化重合によるメチル置換ポリフェニレンスルフィドの合成とその性質2016

    • Author(s)
      齋藤聖也, 田中瑶子, 山﨑智也, 小柳津研一, 西出宏之
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and Properties of Highly Pure Poly(arylene sulfide)s by Oxidative Polymerization of Disulfide2016

    • Author(s)
      M. Aoki, K. Oyaizu, H. Nishide
    • Organizer
      IUPAC International Conference on Advanced Polymeric Materials Commemorating the 40th Anniversary of the Polymer Society of Korea (PSK40)
    • Place of Presentation
      Jeju (Korea)
    • Year and Date
      2016-10-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 酸化重合によるアルキル置換ポリフェニレンスルフィドの合成と熱的性質2016

    • Author(s)
      山﨑智也, 青木港, 小柳津研一, 西出宏之
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      横浜
    • Year and Date
      2016-09-14
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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