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Efficient Synthesis of Rotaxane Cross-linked Polymer Based on the Catalyst-free Click Reaction

Research Project

Project/Area Number 18K14279
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 35020:Polymer materials-related
Research InstitutionGunma University

Principal Investigator

Tsutauba Toyokazu  群馬大学, 大学院理工学府, 研究員 (70807396)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2019: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2018: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsニトリルオキシド / ロタキサン架橋高分子 / 無触媒クリック反応 / 後架橋反応 / エラストマー / 架橋高分子 / ロタキサン / [2]ロタキサン / 超分子化学 / [2]ロタキサ ン
Outline of Final Research Achievements

A rotaxane cross-linking reagent containing two nitrile oxide groups that efficiently reacts with unsaturated-bonds was successfully synthesized. The rotaxane cross-linked polymer composed of common polymer was obtained in high yield via the catalyst-free click reaction of the rotaxane cross-linking regent. The resulting polymer showed superior breaking elongation and strength to that of polymer cross-linked by covalent bond. These results demonstrated that the rotaxane moieties introduced by post modification acted as the movable cross-linking point.

Academic Significance and Societal Importance of the Research Achievements

架橋点が可動可能なロタキサン架橋高分子は次世代の高分子材料として注目を集めているが、高分子中にロタキサン構造を導入する手法は限定されていた。一方、本手法は不飽和結合を有する様々な汎用高分子へ後修飾によりロタキサン構造を付与することができる。これにより大きな合成法の変更なく様々な主鎖構造のロタキサン架橋高分子を得ることができ、その利用範囲は大きく広がると期待される。また無触媒反応による架橋は工業的プロセスや低環境負荷の観点からも優位であり、より実用的な手法であると言える。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Products Report
  • Research Products

    (18 results)

All 2021 2020 2019 2018

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (13 results) (of which Int'l Joint Research: 2 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Rotaxane-Based Difunctional Nitrile N-Oxide Crosslinker : Synthesis and Direct Introduction of Movable Crosslinking Points into Ethylene-Propylene-Butadiene Monomer(EPDM) Rubber2021

    • Author(s)
      Sogawa Hiromitsu、Tsutsuba Toyokazu、Sakiyama Naoto、Ikeda Tatsuhito、Takata Toshikazu
    • Journal Title

      Macromolecular Rapid Communications

      Volume: 42 Issue: 7 Pages: 2000639-2000639

    • DOI

      10.1002/marc.202000639

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Polyester nitrile N-oxides for click reactions synthesized with nitroalkane precursors as the initiator2020

    • Author(s)
      筒場豊和・曽川洋光・高田十志和
    • Journal Title

      Polymer Chemistry

      Volume: - Issue: 18 Pages: 3115-3119

    • DOI

      10.1039/d0py00278j

    • Related Report
      2019 Annual Research Report Products Report
    • Peer Reviewed
  • [Journal Article] Nitrile N-oxide-terminated poly(N-benzyl L-glutamate) (PBLG): synthesis and catalyst-free grafting onto polybutadiene (PBD) and natural rubber (NR)2020

    • Author(s)
      曽川洋光・高松将平・筒場豊和・高田十志和
    • Journal Title

      Polymer Journal

      Volume: -

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nitrile N-oxide-terminated poly(γ-benzyl L-glutamate)(PBLG) : synthesis and catalyst-free grafting onto polybutadiene (PBD) and natural rubber (NR)2020

    • Author(s)
      Sogawa Hiromitsu、Takamatsu Shohei、Tsutsuba Toyokazu、Takata Toshikazu
    • Journal Title

      Polymer Journal

      Volume: 52 Issue: 9 Pages: 1165-1171

    • DOI

      10.1038/s41428-020-0370-5

    • NAID

      40022335752

    • Related Report
      Products Report
    • Peer Reviewed
  • [Presentation] ニトリル N-オキシドの逐次的無触媒クリック反応によるジブロックコポリマーの合成2019

    • Author(s)
      筒場豊和・高田十志和
    • Organizer
      第68回高分子学会年次大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Catalyst-Free Sequential Click Reaction using Bifunctional Nitrile N-Oxide2019

    • Author(s)
      石井歩、筒場豊和、高田十志和
    • Organizer
      日本化学会第99回春季年会(2019)
    • Related Report
      Products Report
  • [Presentation] ニトリルN-オキシドの無触媒クリック反応による高密度グラフトポリマーの合成2019

    • Author(s)
      筒場豊和、高田十志和
    • Organizer
      第一回高分子学会関東支部北関東地区講演会
    • Related Report
      Products Report
  • [Presentation] ニトリルN-オキシドの逐次的無触媒クリック反応によるジブロックコポリマーの合成2019

    • Author(s)
      筒場豊和、高田十志和
    • Organizer
      第68回高分子学会年次大会
    • Related Report
      Products Report
  • [Presentation] Catalyst- and Solvent-free Modification of Polysiloxane using Stable Nitrile N-Oxide : Grafting and Cross-linking2018

    • Author(s)
      T. Tsutsuba, T. Takata
    • Organizer
      IPC 2018
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 安定ニトリル N-オキシドを用いたポリシロキサンの無触媒修飾及び架橋2018

    • Author(s)
      筒場豊和、高田十志和
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
  • [Presentation] 二官能性安定脂肪族ニトリルN-オキシドを用いる無触媒架橋2018

    • Author(s)
      池田 立人、筒場 豊和、曽川 洋光、高田 十志和
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
  • [Presentation] 無触媒クリック反応による高密度グラフトポリマーの効率合成2018

    • Author(s)
      筒場豊和、高田十志和
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report Products Report
  • [Presentation] オルソゴナルクリック反応剤の合成と高分子連結への応用2018

    • Author(s)
      石井歩、筒場豊和、高田十志和
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report Products Report
  • [Presentation] オルソゴナルクリック反応剤を用いたジブロックコポリマーの高効率合成2018

    • Author(s)
      石井歩、筒場豊和、高田十志和
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report Products Report
  • [Presentation] 安定ニトリルN-オキシドを用いたポリシロキサンの無触媒修飾及び架橋2018

    • Author(s)
      筒場豊和、高田十志和
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      Products Report
  • [Presentation] 二官能性安定脂肪族ニトリルN-オキシドを用いる無触媒架橋2018

    • Author(s)
      池田立人、筒場豊和、曽川洋光、高田十志和
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      Products Report
  • [Presentation] Catalyst- and Solvent-free Modification of Polysiloxane using Stable Nitrile N-Oxide : Grafting and Cross-linking2018

    • Author(s)
      Toyokazu Tsutsuba, Toshikazu Takata
    • Organizer
      IPC 2018
    • Related Report
      Products Report
    • Int'l Joint Research
  • [Patent(Industrial Property Rights)] Rotaxane compound2019

    • Inventor(s)
      NAKAHATA SHOKO
    • Industrial Property Rights Holder
      SUMITOMO RUBBER INDUSTRIES
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      Products Report
    • Overseas

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Published: 2018-04-23   Modified: 2022-04-15  

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