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Structurally-Controlled Synthesis of Amphiphilic Polymers Having Tetrahydropyrans in their Main Chains by Ring-Opening Polymerization Meghod and Appearance of their Functions

Research Project

Project/Area Number 63470096
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionNagoya University

Principal Investigator

OKADA Masahiko  Nagoya University, Faculty of Agriculture, Professor, 農学部, 教授 (20023103)

Co-Investigator(Kenkyū-buntansha) SUMITOMO Hiroshi  Nagoya University, Emeritus Professor, 名誉教授 (70023372)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥5,100,000 (Direct Cost: ¥5,100,000)
Fiscal Year 1989: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1988: ¥4,400,000 (Direct Cost: ¥4,400,000)
KeywordsRing-Opening Polymerization / Amphiphilic Polymer / Bicyclic Oxalactone / Bicyclic Oxalactam / Tetrahydropyran Ring / Polyester / Polyamide / Cyclic Oligomer / 環状オリゴマー
Research Abstract

1. Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams
Two new bicyclic oxalactams, 2-oxa-5-azabicyclo[2.2.2]octan-6-one (2,5-BOL) and 2-oxa-6-azacicyclo[2.2.2]octan-5-one (2,6-BOL) were synthesized and their ring-opening polymerizabilities were examined. 2,5-BOL was polymerized in the presence of potassium pyrrolidonate and N-benzoyl BOL as catalyst and activator respectively to give a polyamide having cis-2,5-linked tetrahydropyran rings in the main chain.
The corresponding polyamide consisting of trans-2,5-linked tetrahydropyran rings was prepared by direct polycondensation of trans-5-amino-tetrahydropyran-2-carboxylic acid using triphenyl phosphine and hexachloroethane as activators. The trans-polyamide was much less soluble in comon organic solvents compared with the cis polyamide, and it dissolves in trifluoroethanol, hexafluoro-2-propanol, and m-cresol. 2,6-BOL did not undergo-anionic polymeri- zation, and afforded only a dimeric adduct in a low yield. In contra … More st, 2,6-BOL was polymerized relatively easily with cationic initiators such as trifluoro- methanesulfonic acid to give oligoethers containing 6-membered lactam rings in the main chains.
2. Synthesis of Polyesters Having Tetrahydropyran Rings in their Main Chains
Chains A polyester composed of trans-2,5-linked tetrahydropyran rings was prepared by direct polycondensation using triphenyl phosphine and hexachloroethane as activators. The polyester became highly crystalline after annealing at elevated temperature, and showed limited solubility in organic solvents. Three 2,6- dioxabicyclo[2.2.2]octan-3-one derivatives having at 4-position an ester group of which alcohol moiety was oligooxyethylene chains or a benzyl group were newly prepared. These monomers readily underwent cationic polymerization to produce polyesters having 2,5-linked tetrahydropyran rings in the backbones and the corresponding ester groups as the side chains. The polyesters showed much improved solubilities compared with the parent polyester without ester side chains. These polyesters were very slowly hydrolyzed at 30゚C when their films were immersed in a boffer solution adjusted at pH7.2. Less

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] 岡田鉦彦: "ヘテロ双環化合物の開鎖重合" 有機合成化学協会誌. 47. 1040-1050 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams.2-Oxa-6-azabicyclo[2.2.2]octan-5-one" Macromolecules. 印刷中. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M.Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams.2-Oxa-5-azabicyclo[2.2.2]octan-5-one" J.Polymer Science,Part A. 印刷中. (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H.Sumitomo: "Ring-Opening Polymerization of Bicyclic Oxalactams.Telechelics,Macromers,and Block and Graft Copolymers,in "Frontiers of Macromolecular Science"" Blackwell Scientific Publications, 6 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Okada: "Ring-Opening Polymerization of Heterobicyclic Compounds" J. Synth. Org. Chem., Jpn., 47, 1040-1050 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams. 2-Oxa-6-aza-bicyclo[2.2.2]octan-5-one" Macromolecules.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] M. Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams. 2-Oxa-5-aza-bicyclo[2.2.2]octan-6-one" J. Polym. Sci.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] H. Sumitomo: "Ring-Opening Polymerization of Bicyclic Oxalactams. Telechelics, Macromers, and Block and Graft Copolymers, in "Frontiers of Macromolecular Science"" Backwell Scientific Publications, 125-130 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 岡田鉦彦: "ヘテロ双環化合物の開環重合" 有機合成化学協会誌. 47. 1040-1050 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams.2-Oxa-6-azabicyclo〔2.2.2〕octan-5-one" Macromolecules. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Okada: "Synthesis and Ring-Opening Polymerization of Novel Bicyclic Oxalactams.2-Oxa-5-azabicylo〔2.2.2〕octan-5-one" J.polymer Scienec,Part A. (1990)

    • Related Report
      1989 Annual Research Report
  • [Publications] H.Sumitomo: "Ring-Opening Polymerization of Bicylic Oxalactams.Telechelics,Macromers,and Block and Graft Copolymers,in“Frontiers of Macromolecular Science"" Blackwell Scientific Publications, 6 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] M.Okada: Polymer Journal. 20. 55-63 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Okada: Macromoleclules.

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Okada: Macromolecules.

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Okada: Makromolekulare Chemie.

    • Related Report
      1988 Annual Research Report
  • [Publications] M.Okada: Makromolekulare Chemie,Rapid Communication.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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