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Development of Novel Biodegradable Aliphatic Polyesters Prepared by Catalysts Containing Metals

Research Project

Project/Area Number 11217211
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionHiroshima University

Principal Investigator

SHIRAHAMA Hiroyuki  Hiroshima University, Center for Technology Research and Development, Associate Professor, 地域共同研究センター, 助教授 (60127660)

Co-Investigator(Kenkyū-buntansha) TAMAI Hisashi  Hiroshima University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (40106802)
YASUDA Hajime  Hiroshima University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (00028200)
Project Period (FY) 1999 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥15,600,000 (Direct Cost: ¥15,600,000)
Fiscal Year 2002: ¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2001: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2000: ¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 1999: ¥4,900,000 (Direct Cost: ¥4,900,000)
KeywordsBiodegradable polymers / Aliphatic polyesters / Lactide / Caprolactone / Depsipeptide / Optical activity / Functionalized copolymers / Reactive double bond / 環状カーボネート / 熱的・機械的特性 / ラクトン / 4-アルキルカプロラクトン / エチレンカーボネート / 金属含有触媒
Research Abstract

Poly (L-1actic acid), namely poly (L-lactide) [poly (L-LA)] has such advantages as good biocompatibility and mechanical properties. However, the major problems of poly (L-LA) are its brittleness and low biodegradability. Therefore, in this work, to improve these disadvantages of poly (L-LA), but keeping its advantages, we have prepared novel biodegradable aliphatic polyesters. The following significant results were obtained
Improvement of biodegradability of poly (L-LA) by introducing depsipetide (DP) units ; The enzymatic degradation of poly (L-LA) was much improved by copolymerizing DP monomer (DPs were synthsized from various amino asids and hydoxy acid derivatives). Furthermore, it was found that the biodegradability was most improved by using DP monmers prepared from L-isomers of amino asids.
Improvement of brittleness of poly (L-LA) chains ; The introduction of caprolactone (CL) or its derivative (4-alkylated caprolactone) units into poly (L-LA) chains resulted in a greater improvement of the brittleness of poly (L-LA). And this enabled us to regulate the degradability of copolymers.
The above results rendered us to prepare DP/CL/L-LA terpolymers. The terpolymer with composition ratio about 5/20/75 was found to be the best polymer judging by the balance of biodegradability and properties.
For many applications of biodegradable polymers, functionalizations of these polymers are very important. We have therefore prepared L-LA copolymers having various **nctinal groups. For example, CL/L-LA copolymers with hydroxy group was found to be highly biodegradable compared with poly (L-LA). Further, we have synthesized the copolymers with multifunctional groups (double bond/epoxy/diol) by transforming the reactive double bond of polymers into these functional groups. Finally, we have succeeded in developing cross-linked hydrogel polymers by chemical modification of these groups.

Report

(5 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (41 results)

All Other

All Publications (41 results)

  • [Publications] 白浜博幸: "環状デプシペプチド/ε-カプロラクトン共重合体の合成と生分解性 -ヒドロキシ酸ユニットの影響-"高分子論文集. 56. 77-85 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis and Enzymatic Degradation of Optically Active Depsipeptide Copolymers"J.Biomater.Sci.Polym.Edn.. 10. 621-639 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hajime Yasuda: "Syntheses and Physical Properties of Novel Optically Active Poly(ester-carbonate)s by Copolymerization of Substituted Trimethylene Carbonate with s-Caprolactone and Their Biodegradation"Macromolecules. 32. 6047-6057 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 白浜博幸: "デプシペプチド/ラクトン/ラクチド三元共重合体の調製とその酵素分解性"高分子論文集. 56. 550-556 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis, Chain Extension and Enzymatic Degradation of Aliphatic-Based Polyesters Containing an Aromatic Unit"J.Jpn.Oil Chem.Soc.. 48. 911-915 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis and Biodegradability of Copolymers of Ethylene Carbonate with Lactones"Polym.J.. 32. 280-286 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis and Enzymatic Degradation of High Molecular Weight Aliphatic Polyesters"J.Appl.Polym.Sci.. 80. 340-347 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis and Biodegradability of Monoalkylated Caprolactone Copolymers"J.Oleo Sci.. 50. 191-200 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Synthesis of Poly(lactide-ran-MOREL) and Its Biodegradation with Proteinase K"J.Polym.Sci. ; Part A : Polym. Chem.. 39. 1374-1381 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 堤 主計: "光学活性L-ラクチド/1-メチルトリメチレンカーボネート共重合体の合成と酵素分解"高分子論文集. 58. 245-253 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Highly Biodegradable Copolymers Composed of Chiral Depsipeptide and L-Lactide Units with Favorable Physical Properties"J.Polym.Sci., Part A : Polym.Chem.. 40. 302-316 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Chikara Tsutsumi: "Enzymatic Degradation of Copolymers of L-Lactide with Cyclic Carbonates"Macromol.Biosci.. 2. 223-232 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 白浜博幸(分担, 井上義夫監修): "グリーンプラスチック最新技術(基礎編第4章「新規ラクチド共重合体の合成」)"(株)シーエムシー出版. 1-304 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 白浜博幸(分担): "生分解性プラスチックの改質技術と成形加工における課題と対策(第1章生分解性プラスチックの分解速度の設計およびコントロール技術 第2節脂肪族ポリエステル)"技術情報協会(8月発行予定). (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shiroahama, K.Umemoto, H.Yasuda: "Synthesis and Biodegradation of Cyclic Depsipeptide/ε-Caprolactone Copolymers-Effect of Hydroxy Acid Unit-"Kobunshi Ronbunshu. 56. 77-85 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shiroahama, K.Umemoto, H.Yasuda: "Synthesis and Enzymatic Degradation of Optically Active Depsipeptide Copolymers"J. Biomater. Sci. Polym. Edn.. 10. 621-639 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Yasuda, M.S.Aludin, N.Kitamura, M.Tanabe, H.Shirahama: "Syntheses and Physical Properties of Novel Optically Active Poly (ester-carbonate) s by Copolymerization of Substituted Trimethylene Carbonate with ε-Caprolactone and Their Biodegradation"Macromolecules. 32. 6047-6057 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, A.Tanaka, M.Nagasawa, H.Yasuda: "Preparation and Enzymatic Degradation of Depsipeptide/Lactone/Lactide Terpolymers"Kobunshi Ronbunshu. 56. 550-556 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, H.Hori, H.Yasuda: "Synthesis, Chain Extension and Enzymatic Degradation of Aliphatic-Based Polyesters Containing an Aromatic Unit"J. Jpn. Oil Chem. Soc.. 48. 911-915 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, H.Kanetani, H.Yasuda: "Synthesis and Biodegradability of Copolymers of Ethylene Carbonate with Lactones"Polym. J.. 32. 280-286 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, Y.Kawaguchi, M.S.Aludin, H.Ysuda: "Synthesis and Enzymatic Degradation of High Molecular Weight Aliphatic Polyesters"J. Appl. Polym. Sci.. 80. 340-347 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, N.Kanamori, H.Yasuda: "Synthesis and Biodegradability of Monoalkylated Caprolactone Copolymers"J. Oleo Sci.. 50. 191-200 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, K.Mizuma, K.Umemoto, H.Yasuda: "Synthesis of Poly (lactide-ran-MOHEL) and Its Biodegradation with Proteinase K"J. Polym. Sci. ; Part A : Polym. Chem.. 39. 1374-1381 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] C.Tsutsumi, K.Nakagawa, H.Shirahama, H.Yasuda: "Synthesis and Enzymatic Degradation of Optically Active L-Lactide/1-Methyltrimethylene Carbonate Copolymers"Kobunshi Ronbunshu. 58. 245-253 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] H.Shirahama, A.Tanaka, H.Yasuda: "Highly Biodegradable Copolymers Composed of Chiral Depsipeptide and L-Lactide Units with Favorable Physical Properties"J. Polym. Sci. : Part A : Polym. Chem.. 40. 302-316 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] C.Tsutsumi, K.Nakagawa, H.Shirahama, H.Yasuda: "Enzymatic Degradations of Copolymers of L-Lactide with Cyclic Carbonates"Macromol. Biosci.. 2. 223-232 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hiroyuki Shirahama: "Highly Biodegradable Copolymers Composed of Chiral Depsipeptide and ^L-Lactide Units with Favorable Physical Properties"J. Polym. Sci., Part A : Polym. Chem.. 40. 302-316 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Chikara Tsutsumi: "Enzymatic Degradation of Copolymers of ^L-Lactide with Cyclic Carbonates"Macromol. Biosci.. 2. 223-232 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 白浜 博幸(井上義夫監修): "グリーンプラスチック最新技術(基礎編第4章「新規ラクチド共重合体の合成」)"(株)シーエムシー出版. 304 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis of Poly(lactide-ran-MOHEL) and Its Biodegradation with Proteinase K"J.Polym.Sci.: Part A : Polym.Chem.. 39. 1374-1381 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 堤 主税: "光学活性L-ラクチド/1-メチルトリメチレンカーボネート共重合体の合成と酵素分解性"高分子論文集. 58. 245-253 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Highly Biodegradable Copolymers Composed of Chiral Depsipeptide and L-Lactide Units with Favorable Physical Properties"J.Polym.Sci.: Part A : Polym.Chem.. 40. 302-316 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis and Biodegradability of Copolymers of Ethylene Carbonate with Lactones"Poly.J.. 32・3. 280-286 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis and Biodegradability of Monoalkylated Caprolactone Copolymers"J.Oleo Sci.. 50・3. 191-200 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis and Enzymatic Degradation of High Molecular Weight Aliphatic Polyesters"J.Appl.Polym.Sci.. 80・3. 340-347 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] 白浜博幸: "環状デプシペプチド/ε-カプロラクトン共重合体の合成と生分解性-ヒドロキシ酸ユニットの影響-"高分子論文集. 56・2. 77-85 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis and Enzymatic Degradation of Optically active Depsipeptide Copolymers"J.Biomater.Sci.Polym.Edn.. 10・6. 621-639 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hajime Yasuda: "Syntheses and Physical Properties of Novel Optically Active Poly(ester-carbonate)s by Copolymerization of Substituted Trimethylene Carbonate with ε-Caprolactone and Their Biodegradation Behavior"Macromolecuules. 32・19. 6047-6057 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] 白浜博幸: "デプシペプチド/ラクトン/ラクチド三元共重合体の調製とその酵素分解性"高分子論文集. 56・9. 550-556 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis, Chain Extension and Enzymatic Degradation of Aliphatic-Based Polyesters Containing an Aromatic Unit"J.Jpn.Oil.Chem.Soc.. 48・9. 911-915 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Hiroyuki Shirahama: "Synthesis and Biodegradability of Copolymers of Ethylene Carbonate with Lactons"Polym.J.. 32・3(in press). (2000)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2018-03-28  

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