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1996 Fiscal Year Final Research Report Summary

Design, Development and Industrial Applications of Latent Polymerization and Curing Catalysts

Research Project

Project/Area Number 07555291
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section試験
Research Field 高分子合成
Research InstitutionTokyo Institute of Technology

Principal Investigator

ENDO Takeshi  Tokyo Institute of Technology, Research Laboratory of Resources utilization, Professor, 資源化学研究所, 教授 (40016738)

Co-Investigator(Kenkyū-buntansha) TACHIKAWA Hiroyuki  Asahi Denka Kogyo K.K., New Material Research Laboratory, Researcher, 新材料研究所, 研究員
NOMURA Ryoji  Tokyo Institute of Technology, Research Laboratory of Resources Utilization, Res, 資源化学研究所, 助手 (40242317)
Project Period (FY) 1995 – 1996
KeywordsPolymerization / Curing / Latent Catalyst / Vinyl Ether / Carboxylates / Epoxides / Aminimides / Polymerization Catalysts
Research Abstract

Previous research on the latent polymerization catalysts focused on the design and synthesis of various onium salts such as phosphonium, pyridinium and sufonium salts as well as evaluation of their activity as latent catalysts. This is simply because of the facility of their preparation and in the control of the activity by modifying their substituents. However, low solubility of onium salts in organic solvents or monomers and inorganic residue in polymers or resigns often cause serious problems in the practical usage. Additionally, the monomers which can be polymerized by the previously reported catalysts are limited to cationically polymerizable monomers such as epoxides and vinyl ethers.
The motivations of this research include the development of 1) non-salt type latent polymerization catalysts with high solubility ans latency, and 2) novel latent catalysts which are active for anionic polymerization of electrophilic monomers. As results, several carboxylates and sulfonates were found to serve as non-salts-type latent catalysts for the polymerization of substituted epoxides and vinyl ethers. Anionic polymerization of epoxides was also possible by using aminimides as a latent polymerization catalyst. The aminimides exhibited typical behavior as latent polymerization catalysts, no activity was observed below 80゚C whereas they works as initiator by heating above 100゚C.The initiation mechanism of the aminimide-induced polymerization involves the thermal decomposition of the catalyst into isocyanates along with the formation of tertiary amines which serves as a initiation species. We also succeeded in the preparation of aminimide with hydroxyl group which serves as a novel "latent monomer" by heating, leading to the formation of polyurethanes or pplyureas.

  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] Shinji Nakano: "Catonic Polymerization of Glycidyl Phenyl Ether by Benzylammounium Satts" J.Polym.Sci.,Part A : Polym.Chem.33. 505-512 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Bong Lee: "Hydrazinium Salts as Novel Thermally Latent Bronsted Acid-Inducing Initiator" Chem.Lett.287-288 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takeshi Moriguchi: "Addition-Elimination Reaction in the Trifluoroacetylation of Electron-Rich Olefins" J.Org.Chem.60. 3523-3528 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takeshi Moriguchi: "Possibility of Carboxylic Acid Esters as Thermally Latent Initiators" Macromolecues. 28. 4334-4339 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shinji Nakano: "Synthesis and Properties of Substituted Benzyl Pyridinium Salts as Cationic Initiator" J.Polym.Sci.,Part A : Polym.Chem.34. 475-480 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Do Lee: "Arensulfonates as Non-Salt-Type Latent Thermal Initiators for Cationic Polymerization" Macromolecules. 29. 3317-3319 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Do Lee: "Thermal Latency and Structure-Activity Relationship of Aminimdes in the polymerization of Epoxides" J.Polym.Sci.,Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Do Lee: "Thermo Initiated Polymerization of Glycidyl Phenyl Ether by Arenesulfonates" J.Polym.Sci.,Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Do Lee: "A Novel Synthetic Method of a Polyurethane from an Aminimide as a Latent Monomer" J.Polym.Sci.,Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takeshi Endo: "Design of Latent Catalysts and Their Application to ..." Macromol.Symp.107. 237-242 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shinji Nakano: "Thermal Cationic Curing with Benzylammonium Salts-2" Prog.Org.Coat.28. 143-148 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sang-Bobg-Lee: "Cationic Polymerization of Styrene with N-Benzyl Pyridinium Salts. Isolation of Polymeric Cationic ...." Chem.Lett.983-984 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 三田文雄: "新しい潜在性触媒の設計と高分子合成への応用" 高分子. 45. 128-131 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 仲野伸司: "α.α-ジメチルベンジルピリジニウム塩の熱潜在性開始剤としての評価と応用" 日本接着学会誌. 32. 272-277 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yusuf Yagci: "N-Benzyl and N-alkoxy Pyridinium Salts as Thermal and ..." Adv.Polym.Sci.127. 59-86 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Shinji NAKANO and Takeshi ENDO: "Cationic Polymerization of Glycidyl Phenyl Ether by Benzylammonium Salts" Polym.Sci., Part A : Polym.Chem.33. 505 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Bong LEE,Young-Suk PARK,Kyu-Wan LEE and Takeshi ENDO: "Hydrazinium Salts as Novel Thermally Latent Bronsted Acid-Inducing Initiators" Chem.Lett.287 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takeshi MORIGUCHI and Takeshi ENDO: "Addition-Elimination Reaction in the Trifluoroacetylation of Electron-Rich Olefins" J.Org.Chem.60. 3523 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takeshi MORIGUCHI,Toshikazu TAKATA,Yoshinori NAKANE and Takeshi ENDO: "Possibility of Carboxylic Acid Esters as Thermally Latent Initiators" Macromolecules. 28. 4334 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shinji NAKANO and Takeshi ENDO: "Synthesis and Properties of alpha-Substituted Benzylpyridinium Salts as Cationic Initiators" J.Polym.Sci., Part A : Polym.Chem.34. 475 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Do LEE,Toshikazu TAKATA and Takeshi ENDO: "Arenesulfonates as Non-Salt-Type Latent Thermal Initiators for Cationic Polymerization" Macromolecules. 29. 3317 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takeshi ENDO and Fumio SANDA: "Design of Latent Catalysts and Their Application to Polymer Synthesis" Macromol.Symp.107. 237 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shinji NAKANO and Takeshi ENDO: "Thermal Cationic Curing with Benzylammonium Salts-2" Prog.Org.Coat.28. 143 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Bong LEE,Kyu-Wan LEE,Toshikazu TAKATA and Takeshi ENDO: "Cationic Polymerization of Stirene with N-Benzyl Pyridinium Salt. Isolation of Polymeric Cationic Species and Its Application to Block Copolymer Synthesis" Chem.Lett.983 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fumio SANDA and Takeshi ENDO: "Design of Novel Latent Catalysts and Their Application to Polymer Synthesis" Kobunshi. 45. 128 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Shinji NAKANO and Takeshi ENDO: "Evaluation of alpha, alpha-Dimethylbenzylpyridinium Salts as Latent Thermal Cationic Initiator and Their Application to Crosslinking Rcactions" Adhesion. 32. 272 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yusuf YAGCI and Takeshi ENDO: "N-Benzyl and N-Alkoxy Pyridinium Salts as Thermal and Photochemical Initiators for Cationic Polymerization" Adv.Polym.Sci.59. 127 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Do LEE,Fumio SANDA and Takeshi ENDO: "Thermal Latency and Structure-Activity Rclationship of Aminimides in the Polymerization of Epoxide" J.Polym.Sci., Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Do LEE,Toshikazu TAKATA and Takeshi ENDO: "Thermo-Initiated Cationic Polymerization of Glycidyl Phenyl Ether by Arenesulfonates" J.Polym.Sci., Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sang-Do LEE,Fumio SANDA and Takeshi ENDO: "A Novel Synthetic Method of a Polyurethane from and Aminimide as a Latent Monomer" J.Polym.Sci., Part A : Polym.Chem.(in press).

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1999-03-09  

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