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Design of Polyurethanes and Poly(urethanurea)s Derived from Saccharides and Amino Acids and Control of Their Hydrolyzability

Research Project

Project/Area Number 12650871
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionKogakuin University

Principal Investigator

HASHIMOTO Kazuhiko  Kogakuin Univ., Faculty of Eng. Professor, 工学部, 教授 (20023484)

Co-Investigator(Kenkyū-buntansha) OKAWA Haruki  Kogakuin Univ., Faculty of Eng. Assistant Prof., 工学部, 講師 (50221122)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2001: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2000: ¥2,900,000 (Direct Cost: ¥2,900,000)
KeywordsL-Gulonic Acid / Polyurethanes / Poly(urethanurea)s / Polyaddition / Biodegradable Polymers / Saccharides / Amino Acids / Eco-materials
Research Abstract

Naturally occurring polymers and their composites have been noted again as renewable resources. Recently macromolecular syntheses from their repeating units such as monosaccharides and amino acids have been reported by several investigators. In the present work we synthesized two kinds of diols (2,3- and 5,6-0-isopropylidene-L-gulono-1,4-lactones(1 and 2) from L-gulonolactone. New polyurethanes (4, 5, 6, 7) having lactone groups in the pendants and main chains were synthesized through the polyaddition of the saccharide-derived diols(1 and 2) with L-Lysine-derived diisocyanate, methyl(S)-2,6-diisocyanatohexanoate (3), and the following deisopropylidene reaction. The polyurethanes having pendant lactone groups (4 and 6) were found to be hydrolyzed more rapidly than those having lactone groups in the main chains (5 and 7) respectively, in the buffer solution of which the pH value was 8.0 or 7.0 at 27℃. The hydroxyl groups generated by the deprotection of isopropylidene groups in the polyurethanes also enhanced their hydrolyzability.
Another new polymers, poly(urethanurea)s (8), were synthesized through the polyadditon of L-serine methyl ester with 3. They were also hydrolyzed in the buffer solution of which the pH value was 8.0 or 7.0 although the rate on the hydrolysis of 8 was much lower than that of the polyurethanes (6 and 7).

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] K.Hashimoto: "Mac romolecular Syntheses from Lactones of Saccharic Acids and Acidic Saccharides"Recent Res.Devel.Polymer Science. 3. 13-30 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 橋本和彦: "糖とアミノ酸由来ポリウレタンの設計とその生分解性の制御"工学院大字総合研究所年報. 7. 127-130 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Hashimoto: "Ring-Opening Polymerization of Lactams"Prog.Polym.Sci.. 25(10). 1411-1462 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Shimura, K.Hashimoto, C.Yamanaka, D.Setojima: "Synthesis and Polymerization of New Styryl and Methacryloyl Monomers Containing Acidic Saccharide Moieties"J.Polym.Sci.: Part A : Polym Chem.. 39(22). 3893-3901 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] E.Ito, M.Yamamoto K.Kajikawa, D.Yamashita H.Ishii, Y.Ouchi, K.Seki, H.Okawa, K.Hashimoto: "Orientational Structure of Thiophene Thiol Self-Assembled Monolayer Studied by Using Metastable Atom Electron Spectroscopy and Infrared Reflection Absorption Spectroscopy"Langmuir. 17(14). 4282-4286 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Katsuraya, Y.Imoto, K.Hashimoto, H.Takei, R.Aono, K.Hatanaka: "Synthesis of Oligosaccharide with Controlled Sequence"Carbohydrate Letters. 4(2). 131-136 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Hashimoto: "Macromolecular Syntheses from Lactones of Saccharic Acids and Acidic Saccharides"Recent Res. Devel. Polymer Science. 3. 13-30 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Hashimoto: "Design of Polyurethanes Derived from Saccharides and Amino Acids and Control of Their Biodegradability"The Annual Review of Research Institute for Sciences and Technology, Kogakuin University. 7. 127-130 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Hashimoto: "Ring-Opening Polymerization of Lactams"Prog. Polym. Sci.. 25 (10). 1411-1462 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Shimura, K. Hashimoto, C. Yamanaka, D. Setojima: "Synthesis and Polymerization of New Styryl and Methacryloyl Monomers Containing Acidic Saccharide Moieties"J. Polym. Sci.: Part A: Polym Chem.. 39 (22). 3893-3901 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] E. Ito, M. Yamamoto, K. Kajikawa, D. Yamashita, H. Ishii, Y. Ouchi, K. Seki, H. Okawa, K. Hashimoto: "Orientational Structure of Thiophene Thiol Self-Assembled Monolayer Studied by Using Metastable Atom Electron Spectroscopy and Infrared Reflection Absorption Spectroscopy"Langmuir.. 17 (14). 4282-4286 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Katsuraya, Y. Imoto, K. Hashimoto, H. Takei, R. Aono, K. Hatanaka: "Synthesis of Oligosaccharide with Controlled Sequence"Carbohydrate Letters. 4 (2). 13-136 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Shimura, K.Hashimoto, C.Yamanaka, D.Setojima: "Synthesis and Polymerization of New Styryl and Methacryloyl Monomers Containing Acidic Saccharide Moieties"J.Polym.Sci.:Part A:Polym Chem.. 39(22). 3893-3901 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] E.Ito, M.Yamamoto, K.Kajikawa, D.Yamashita, H.Ishii, Y.Ouchi, K.Seki, H.Okawa, K.Hashimoto: "Orientational Structure of Thiophene Thiol Self-Assembled Monolayer Studied by Using Metastable Atom Electron Spectroscopy and Infrared Reflection Absorption Spectroscopy"Langmuir. 17(14). 4282-4286 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Katsuraya, Y.Imoto, K.Hashimoto, H.Takei, R.Aono, K.Hatanaka: "Synthesis of Oligosaccharide with Controlled Sequences"Carbohydrate Letters. 4(2). 131-136 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Hashimoto,: "Ring-Opening Polymerization of Lactams. Living Anionic Polymerization And Its Application"Prog.Polym.Sci.,. 25. 1411-1462 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Hatanaka,T.Yamaguchi K.Katsuraya,K.Hashimoto: "Synthesis of Mannose Branched Deoxy-Glucan Derivative by Polymerization of Disaccharide Monomer"Polym.J.. 32. 974-976 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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