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Development of controlled polymerization method for aromatic acrylic monomers derived from non-edible biomass resources

Research Project

Project/Area Number 18K05210
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 34030:Green sustainable chemistry and environmental chemistry-related
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

Takenaka Yasumasa  国立研究開発法人理化学研究所, 環境資源科学研究センター, 上級研究員 (40392021)

Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2018: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsアクリル樹脂 / バイオベースポリマー / グループトランスファー重合 / 非可食性バイオマス / リグニン誘導体 / 精密重合 / バイオマスポリマー
Outline of Final Research Achievements

We focus on the development of new high-quality bio-based plastic materials from non-edible biomass resources. In this study, it was found that some organic acid catalysts produce the polymerization of various β-substituted-α,β-unsaturated carboxylates such as alkyl cinnamates. Various alkyl cinnamates were successfully polymerized to give the corresponding polymers in good yields. We show that homopolymers of these compounds with molecular weights (Mw) of ~34,000 g/mol and controlled polymer backbones can be synthesized by the group-transfer polymerization (GTP) technique using organic acid. These homopolymers are shown to have high heat resistance comparable to that of engineering plastics. And then, we show the mechanistic and kinetic analyses for GTP of β-substituted-α,β-unsaturated carboxylates.

Academic Significance and Societal Importance of the Research Achievements

本研究は、重合が難しいといわれていた桂皮酸エステルやカフェ酸エステル誘導体の炭素-炭素二重結合部位での単独重合が進行した新規なアクリルポリマーの合成に成功した初めての例である。得られた重合体の主鎖構造に直接結合する芳香環により、従来のアクリル樹脂とは異なる特徴的な物性の発現が期待できる。本合成技術を用いることで、バイオ生産が可能な同様の化学構造を持つアクリルモノマーあるいは食糧問題と競合しない非可食性バイオマスから誘導される同様の化学構造を持つアクリルモノマーを原料とした新たな機能性アクリル樹脂の製造技術開発が進むと期待される。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (22 results)

All 2021 2020 2019 2018 Other

All Journal Article (6 results) (of which Peer Reviewed: 5 results,  Open Access: 5 results) Presentation (14 results) (of which Int'l Joint Research: 7 results,  Invited: 1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Copolymers incorporated with β-substituted acrylate synthesized by organo-catalyzed group-transfer polymerization2021

    • Author(s)
      Imada Motosuke、Takenaka Yasumasa、Tsuge Takeharu、Abe Hideki
    • Journal Title

      Polymer Journal

      Volume: 53 Issue: 9 Pages: 989-999

    • DOI

      10.1038/s41428-021-00493-z

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Effect of Disyndiotacticity on the Glass Transition Temperature of Poly(ethyl crotonate)s Synthesized by Group-Transfer Polymerization Catalyzed by Organic Acids2020

    • Author(s)
      Imada Motosuke、Takenaka Yasumasa、Tsuge Takeharu、Abe Hideki
    • Journal Title

      Macromolecules

      Volume: 53 Issue: 18 Pages: 7759-7766

    • DOI

      10.1021/acs.macromol.0c01122

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Kinetic modeling study of the group-transfer polymerization of alkyl crotonates using a silicon Lewis acid catalyst2020

    • Author(s)
      Imada Motosuke、Takenaka Yasumasa、Tsuge Takeharu、Abe Hideki
    • Journal Title

      Polymer Chemistry

      Volume: 11 Issue: 37 Pages: 5981-5991

    • DOI

      10.1039/d0py00353k

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] リグニン誘導体から合成される新規アクリル樹脂素材2020

    • Author(s)
      竹中康将
    • Journal Title

      エネルギー・化学・プラントの総合技術誌 JETI

      Volume: Vol. 68, No. 2 Pages: 73-76

    • Related Report
      2019 Research-status Report
  • [Journal Article] Group-Transfer Polymerization of Various Crotonates Using Organic Acid Catalysts2019

    • Author(s)
      Takenaka Yasumasa,* Abe Hideki
    • Journal Title

      Macromolecules

      Volume: 52 Issue: 11 Pages: 4052-4058

    • DOI

      10.1021/acs.macromol.9b00272

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Unique acrylic resins with aromatic side chains by homopolymerization of cinnamic monomers2019

    • Author(s)
      Imada Motosuke, Takenaka Yasumasa,* Hatanaka Hidehito, Tsuge Takeharu, Abe Hideki
    • Journal Title

      Communications Chemistry

      Volume: 2 Issue: 1 Pages: 109-109

    • DOI

      10.1038/s42004-019-0215-3

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 有機酸触媒を用いたグループトランスファー重合によるバイオベースアクリル樹脂の合成2020

    • Author(s)
      竹中康将、今田基祐、阿部英喜
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Research-status Report
  • [Presentation] 再生可能資源を原料とするバイオベースアクリル樹脂合成2020

    • Author(s)
      竹中康将、阿部英喜
    • Organizer
      第9回JACI/GSCシンポジウム
    • Related Report
      2020 Research-status Report
  • [Presentation] 非可食性バイオマスを原料とするバイオベースポリクロトン酸エステルの合成2019

    • Author(s)
      竹中康将、阿部英喜
    • Organizer
      第8回JACI/GSCシンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] Group-Transfer Polymerization of Various Crotonates using Organic Superacid2019

    • Author(s)
      Yasumasa Takenaka, Hideki Abe
    • Organizer
      IUPAC 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Preparation and Characterization of Bio-based Poly(ethyl Crotonate) from Nom-edible Biomass2019

    • Author(s)
      Yasumasa Takenaka, Hideki Abe
    • Organizer
      The 33rd Polymer Degradation Discussion Group (PDDG)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and structural analysis of unique acrylic resins from cinnamic monomers with high thermal resistanece2019

    • Author(s)
      Motosuke Imada, Yasumasa Takenaka, Hidehito Hatanaka, Takeharu Tsuge, Hideki Abe
    • Organizer
      The 33rd Polymer Degradation Discussion Group (PDDG)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Group-Transfer Polymerization of Various Crotonates Catalyzed by Organic Superacid2019

    • Author(s)
      Yasumasa Takenaka, Hideki Abe
    • Organizer
      The 13th IUPAC International Symposium on Ionic Polymerization (IP2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 有機酸触媒を用いたクロトン酸エステル類のグループトランスファー重合と得られるポリマーの物性評価2019

    • Author(s)
      竹中康将、阿部英喜
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 有機酸触媒を用いたグループトランスファー重合によるポリクロトン酸エステルの合成と物性評価2019

    • Author(s)
      竹中康将、阿部英喜
    • Organizer
      第68回高分子討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] Preparation of Bio-based Poly(ethyl Crotonate) by Organic Acid Catalyzed Group-transfer Polymerization2019

    • Author(s)
      Yasumasa Takenaka, Hideki Abe
    • Organizer
      The 7th International Conference on Bio-based Polymer (ICBP2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Structural Analysis and Thermal Property of Unique Acrylic Resin with Aromatic Side Chain from Cinnamate2019

    • Author(s)
      Motosuke Imada, Yasumasa Takenaka, Hidehito Hatanaka, Takeharu Tsuge, Hideki Abe
    • Organizer
      The 7th International Conference on Bio-based Polymer (ICBP2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Group-transfer Polymerization of Various Alkyl Crotonates Using Organic Superacid Catalysts2019

    • Author(s)
      Yasumasa Takenaka, Hideki Abe
    • Organizer
      The 16th Pacific Polymer Conference (PPC)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of High-Performance and Specific Functional Bioplastic Materials from Biomass Resources2019

    • Author(s)
      Yasumasa Takenaka
    • Organizer
      Invited lecture, National Taiwan University
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] バイオマスから誘導可能なα,β-不飽和カルボン酸エステル重合体の合成と物性評価2018

    • Author(s)
      竹中康将、阿部英喜
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report
  • [Remarks] リグニン誘導体からアクリル樹脂の開発に成功

    • URL

      https://www.riken.jp/press/2019/20191017_2/index.html

    • Related Report
      2019 Research-status Report
  • [Patent(Industrial Property Rights)] β置換不飽和カルボン酸エステルの重合体の製造方法2019

    • Inventor(s)
      竹中康将、今田基祐、阿部英喜
    • Industrial Property Rights Holder
      竹中康将、今田基祐、阿部英喜
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2019-200017
    • Filing Date
      2019
    • Related Report
      2019 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2023-01-30  

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