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The development of environmentally benign organophosphorus flame retardant

Research Project

Project/Area Number 25410198
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Green/Environmental chemistry
Research InstitutionOsaka Municipal Technical Research Institute

Principal Investigator

Ito Takatoshi  地方独立行政法人大阪市立工業研究所, 有機材料研究部, 研究室長 (60416295)

Co-Investigator(Kenkyū-buntansha) IWAI Toshiyuki  地方独立行政法人大阪市立工業研究所, 有機材料研究部, 研究主任 (20416291)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2013: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords有機リン化合物 / 添加剤 / クロスカップリング / 難燃剤 / フェノール / 選択的合成 / 環境調和
Outline of Final Research Achievements

Organophosphorus compounds based on 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide derivatives have attracted much attention as environmental benign flame retardants. Various 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide derivatives were efficiently synthesized by Friedel-Crafts reaction of 2-hydroxybiphenyls with phosphorus trichloride in the presence of super acids, especially TfOH as a catalyst. The novel organophosphorus compounds consist of an ether bridge connecting with glutaryl dichloride and sebacoyl chlorides were synthesized. These compounds was determined and characterized by 1H-, 13C- 31P-NMR and TG-DTA data. It was found that the bridged organophosphorus compounds exhibited good thermal stability compared to the 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide. This observation is important for high temperature polymer application requiring for the melt processing conditions.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (16 results)

All 2015 2014 2013

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (11 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] Facile Synthesis of Methanofullerenes in an Aqueous Two-Phase System under Photoirradiation Conditions2015

    • Author(s)
      Toshiyuki Iwai,Fukashi Matsumoto,Koichi Hida,Kazuyuki Moriwaki,Yuko Takao,Takatoshi Ito,Takumi Mizuno,Toshinobu Ohno
    • Journal Title

      Synlett

      Volume: 26 Issue: 07 Pages: 960-964

    • DOI

      10.1055/s-0034-1380127

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Redox-Neutral Iron-Sulfur Promoted Transformation of 2-Nitrophenols and 2,6-Disubstituted p-Cresols into 2-Arylbenzoxazoles2014

    • Author(s)
      Masahiko Saibara, Kazuhito Ashida, Kouji Satomi, Toshiyuki Iwai, Takeo Nakai, Masatoshi Mihara, Takatoshi Ito, Takumi Mizuno
    • Journal Title

      Synlett

      Volume: 25 Issue: 11 Pages: 1565-1570

    • DOI

      10.1055/s-0033-1338995

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and properties of novel fluorinated subnaphthalocyanines for organic photovoltaic cells2014

    • Author(s)
      Yuko Takao, Tomoaki Masuoka, Koji Yamamoto, Tadashi Mizutani, Fukashi Matsumoto, Kazuyuki Moriwaki, Koichi Hida, Toshiyuki Iwai, Takatoshi Ito, Takumi Mizuno, Toshinobu Ohno
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 33 Pages: 4564-4567

    • DOI

      10.1016/j.tetlet.2014.06.069

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of [6,6]-Phenyl-C61/71-Butyric Acid Methyl Esters via Sulfur Ylides for Bulk-Heterojunction Solar Cell2013

    • Author(s)
      Takatoshi Ito, Toshiyuki Iwai, Fukashi Matsumoto, Koichi Hida, Kazuyuki Moriwaki, Yuko Takao, Takumi Mizuno, Toshinobu Ohno
    • Journal Title

      Synlett

      Volume: 24 Issue: 15 Pages: 1988-1992

    • DOI

      10.1055/s-0033-1339481

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] PBO fiber原料 ジアミノレゾルシノールの一酸化炭素・硫黄によるカルボニル化反応2013

    • Author(s)
      水野卓巳、中井猛夫、三原正稔、伊藤貴敏
    • Journal Title

      科学と工業

      Volume: 87 Pages: 147-153

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis of Cyclic Organophosphorus Compounds, 6H-dibenz[c, e][1, 2]oxaphosphorin Derivatives, and Its Applications2015

    • Author(s)
      Takatoshi Ito, Toshiyuki Iwai, Takeo Nakai, Masatoshi Mihara, Takumi Mizuno, Toshinobu Ohno
    • Organizer
      The 2015 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii Convention Center(Honolulu, Hawaii, USA)
    • Year and Date
      2015-12-16
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Selective Flow Synthesis of Methanofullerene Derivative PCBM Using Sulfur Ylide2015

    • Author(s)
      Takatoshi Ito, Yuta Inoue, Tetsuo Iwasawa, Fukashi Matsumoto, Toshiyuki Iwai, Kazuyuki Moriwaki, Yuko Takao, Takumi Mizuno, Toshinobu Ohno
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会館(京都市)
    • Year and Date
      2015-07-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Friedel-Crafts型リン原子導入反応による二官能性リン化合物の合成2015

    • Author(s)
      伊藤貴敏、岩井利之、中井猛夫、三原正稔、水野卓巳、大野敏信
    • Organizer
      第95回日本化学会春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 二酸化炭素とグリセロールからのグリセロールジカーボネート類およびトリカーボネート類の選択的合成2015

    • Author(s)
      三原正稔、諸賀要、岩澤哲郎、中井猛夫、岩井利之、伊藤貴敏、大野敏信、水野卓巳
    • Organizer
      第95回日本化学会春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] トリアリールアミンを有するメタノフラーレンの創製と有薄膜太陽電池デバイスへの応用2015

    • Author(s)
      森脇和之、岩本和樹、岩澤哲郎、松元 深、岩井利之、高尾優子、伊藤貴敏、水野卓巳、大野敏信
    • Organizer
      第95回日本化学会春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] イオウイリドを利用するフラーレンC70 誘導体([70]PCBM)の高位置選択的合成2014

    • Author(s)
      伊藤貴敏、巴山佳祐、岩澤哲郎、松元深、岩井利之、森脇和之、高尾優子、水野卓巳、大野敏信
    • Organizer
      日本プロセス化学会2014サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-07-31
    • Related Report
      2014 Research-status Report
  • [Presentation] 硫黄-鉄触媒存在下,Redox-Neutral反応による2-ニトロフェノールと2,6-二置換p-クレゾールからの2-フェニルベンズオキサゾール合成2014

    • Author(s)
      西原匡彦、芦田一仁、里見亨史、岩井利之、中井猛夫、三原正稔、伊藤貴敏、水野卓巳
    • Organizer
      日本プロセス化学会2014サマーシンポジウム
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2014-07-31
    • Related Report
      2014 Research-status Report
  • [Presentation] イオウイリドを利用するメタノフラーレン誘導体PCBMの効率的フロー合成法2014

    • Author(s)
      伊藤貴敏、井上裕太、岩澤哲郎、松元深、岩井利之、飛彈浩一、森脇和之、高尾優子、水野卓巳、大野敏信
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フローマイクロリアクターを用いた光照射によるメタノフラーレン誘導体PCBMの合成2014

    • Author(s)
      岩井利之、村田隼樹、岩澤哲郎、松元深、飛彈浩一、森脇和之、高尾優子、伊藤貴敏、水野卓巳、大野敏信
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Friedel-Crafts型リン原子導入反応を利用した有機リン系難燃剤中間体の効率的合成法2013

    • Author(s)
      伊藤貴敏、岩井利之、中井猛夫、三原正稔、水野卓巳、大野敏信
    • Organizer
      第40回典型元素討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2013 Research-status Report
  • [Presentation] イオウイリドを利用する有機太陽電池用アクセプター材料の簡便合成法2013

    • Author(s)
      伊藤貴敏、岩井利之、松元深、飛彈浩一、森脇和之、高尾優子、水野卓巳、大野敏信
    • Organizer
      日本プロセス化学会
    • Place of Presentation
      つくば国際会議場
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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