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2002 Fiscal Year Final Research Report Summary

Chemical Synthesis of Biodegradable Polyesters Utilizing Sugar Biomasses.

Research Project

Project/Area Number 11217208
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionChubu University (2000-2002)
Nagoya University (1999)

Principal Investigator

OKADA Masahiko  Chubu University, College of Bioscience and Biotechnology, Professor, 応用生物学部, 教授 (20023103)

Co-Investigator(Kenkyū-buntansha) AOI Keigo  Nagoya University, School of Bioagricultural Sciences, Associate Professor, 大学院・生命農学研究科, 助教授 (30222467)
Project Period (FY) 1999 – 2002
KeywordsBiodegradability / Polyester / Biomass / Sugara Diol / Chitin / Poly (ester amide) / Poly (ester carbonate) / Polycarbonate
Research Abstract

1. Synthesis of Polyesters and Related Polymers Containing Sugar Diols : Series of polyesters, poly (ester amide) s, poly (ester carbonate) s, and polycarbontes were synthesized from sugar-based raw materials. Sugar diols such as 1, 4:3, 6-dianhydro-D-glucitol (DAG), 1, 4:3, 6-dianhydro-D-mannitol (DAM), 1, 4:3, 6-dianhydro-L-iditol (DAl) were chiefly employed as diol components in polycondensations. Dicarboxylic acid derivatives containing furan moieties were used as dicarboxylic acid components in some cases.
2. Biodegradability of Sugar-Based Polyesters and Related Polymers : The biodegradability of the sugar-based polyesters and the related polymers were examined by three different methods, i. e., soil burial degradation, activated sludge treatment, and enzymatic degradation tests. The biodegradability varied widely, depending on the molecular structure of the polymers. In general, polymers containing unsymmetrical DAG units showed higher biodegradability than the corresponding polymers containing symmetrical DAM and DAI units.
3. Synthesis of Chitin-graft-oligoesters and Related Polymer : Chitin-graft-oligoesters were prepared by the ring-opening polymerization of ε-caprolactone in the presence of partially deacetylated chitin (PDC) using water as a medium. A novel N-selective ester functionalized chitin derivative was prepared by a Michael-type nucleophilic addition of an amino group of PDC to ethyl acrylate in phosphate buffer/methanol. Poly (vinyl alcohol)-graft-oligoester was synthesized by the reaction of PVA and ε-caprolactone in DMSO. The biodegradability as well as the thermal and surface properties of these polymer films were examined in detail. On the basis of the present research, useful and important guidelines have been established for designing polyesters and related polymers having a controlled biodegradability from renewable sugar-based raw materials.

  • Research Products

    (40 results)

All Other

All Publications (40 results)

  • [Publications] K.Aoi.: "Synthesis and Assembly of Novel Chitin Derivatives Having Amphiphilic Polyoxazoline Block Conolvmer as a Side Chain"Macromol.Chem.Phys. 200. 1112-1120 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A.Takasu: "New Chitin-Based Polymer Hybrids, 4: Soil Burial Degradation Behavior of Poly(vinyl alcohol)/Chitin Derivative Miscible Blends"J.Appl.Polym.Sci.. 73. 1171-1179 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Biodegradable Polymers Based on Renewable Resources. III. Copolyesters Composed of 1,4:3,6-Dianhydro-D-glucitol, 1,1-Bis(S-car-boxy-2-furyl)ethane, and Aliphatic"J.Appl.Polym.Sci.. 74. 3342-3350 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Sato: "Characterization of Chitin-Based Polymer Hybrids by Temperature Programmed Analytical Pyrolysis Techniques. 2. Chitin-graft poly(2-methyl-2-oxazoline) /Poly(vinyl alcohol)"Macromolecules. 33. 357-362 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Seki: "Synthesis of Chitin Derivatives Having Peptide Side Groups by the Water-Soluble Active Ester Method"Macromol.Chem.Phys.. 201. 439-446 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Aoi: "Polypeptide-Synthetic Polymer Hybrids, 2. Miscibility of Poly(vinyl alcohol) with Polvsarcosine"Macromol.Chem.Phys.. 201. 1059-1066 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Aoi: "Synthesis of a Novel N-Selective Ester Functionalized Chitin Derivative and Water-soluble Carboxyethylchitin"Macromol.Chem.Phys.. 201. 1701-1708 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Biodegradable Polymers Based on Renewable Resources. IV. Enzymatic Degradation ofPolyesters Composed of 1,4:3,6-Dianhydro-D-glucitol and Aliphatic Dicarboxylic Acid"J.Appl.Polym.Chem.. 77. 338-346 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Biodegradable Polymers Based on Renewable Resources, V. Synthesis and BiodegradationBehavior of Poly(ester amides Composed of 1,4:3,6-Dianhydro-D-glucitol, α-Amino Acid"Appl.Polym.Sci.. 81. 2721-2734 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Sato: "A Novel Evaluation Method for Biodegradability of Poly(butylene succinate-co-butyleneadipate) by Pyrolysis-Gas Chromatography"Polym.Degrad.Stab.. 73. 327-334 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] S.Detchprohm: "Synthesis of a Novel Chitin Derivative Having Oligo(E-caprolactone) Side Chains in Aqueous Reaction Media"Macromol.Chem.Phys.. 202. 3560-3570 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Aoi: "Synthesis of a Poly(vinyl alcohol)-Based Graft Copolymer Having Poly(ε-caprolactone)Side Chains by Solution Polymerization"Macromol.Chem.Phys.. 203. 1018-1028 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Sato: "Determrnation of Degree of Substitution in N-Carboxyethylated Chitin Derivatives by Pyrolysis-Gas Chromaography in the Presence of Oxalic Acid"J.Anal.Appl.Pyrolysis. 64. 177-185 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Biodegradable Polymers Based on Renewable Resources, VI. Synthesis and Biodegradability of Polyester carbonate)s Containing 1,4:3,6-Dianhydro-D-glucitol and"J.Appl.Polym.Sci.. 86. 872-880 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Aoi: "Nano-scale Molecular Shapes of Water-soluble Chitin Derivatives Having Monodisperse Poly(2-alkyl-2-oxazolinel Side Chains"Macromol.Chem.Phys.. 203. 2650-2657 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Chemical Syntheses of Biodegradable Polymers"Prog.Polym.Sci.. 27. 87-135 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Okada: "Biodegradable Polymers from 1,4:3,6-Dianhydro-D-glucitol (Isosorbide) and Its Related Compounds"Current Trends in Polymer Science. 7. 57-70 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Yokoe: "Biodegradable Polymers Based on Renewable Resources, VII. Synthesis of Novel Random and Alternating Copolycarbonates from 1,4:3,6-Dianhydrohexitols and Aliphatic Diols"J.Polym.Sci. : Part A : Polym.Chem.. 40. 2312-2321 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 岡田鉦彦: "グリーンプラスチック最新技術(第7章)"シーエムシー出版. 304 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 岡田鉦彦: "生分解性高分子の改質技術と成型加工における課題と対策(第2章第4節)"技術情報協会(印刷中). (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Aoi, A.Takasu, M.Okada, T.Imae: "Synthesis and Assembly of Novel Chitin Derivatives Having Amphiphilic Polyoxazoline Blook Copolymer as a Side Chain"Macromol. Chem. Phys.. 200. 1112-1120 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A.Takasu, K.Aoi, M.Tsuchiya, M.Okada: "New Chitin-Based Polymer Hybrids, 4 : Soil Burial Degradation Behavior of Poly (vinyl alcohol)/Chitin Derivative Miscible Blends"J. Appl. Polym. Sci.. 73. 1171-1179 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada, K.Tachikawa, K.Aoi: "Biodegradable Polymers Based on Renewable Resources. III. Copolyesters Composed of 1, 4:3, 6-Dianhydro-D-glucitol, 1, 1-Bis (5-car-boxy-2-furyl) ethane, and Aliphatic Dicarboxylic Acid Units"J. Appl. Polym. Sci.. 74. 3342-3350 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Sato, H.Ohtani, S.Tsuge, K.Aoi, A.Takasu, M.Okada: "Characterization of Chitin-Based Polymer Hybrids by Temperature Programmed Analytical Pyrolysis Techniques. 2. Chitin-graft-poly (2-methyl-2-oxazoline) /Poly (vinyl alcohol) Blends"Macromolecules. 33. 357-362 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Seki, K.Aoi, M.Okada, Y.Shiogai: "Synthesis of Chitin Derivatives Having Peptide Side Groups by the Water-Soluble Active Ester Method"Macromol. Chem. Phys.. 201. 439-446 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Aoi, R.Nakamura, M.Okada: "Polypeptide-Synthetic Polymer Hybrids, 2. Miscibility of Poly (vinyl alcohol) with Polysarcosine"Macromol. Chem. Phys.. 201. 1059-1066 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Aoi, T.Seki, M.Okada, H.Sato, S.Mizutani, H.Ohtani, S.Tsuge, Y.Shiogai: "Synthesis of a Novel-N-Selective Ester Functionalized Chitin Derivative and Water-soluble Carboxyethylchitin"Macromol. Chem. Phys.. 201. 1701-1708 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada, K.Tsunoda, K.Tachikawa, K.Aoi: "Biodegradable Polymers Based on Renewable Resources. IV. Enzymatic Degradation of Polyesters Composed of 1, 4:3, 6-Dianhydro-D-glucitol and Aliphatic Dicarboxylic Acid Moieties"J. Appl. Polym. Chem.. 77. 338-346 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada, M.Yamada, M.Yokoe, K.Aoi: "Biodegradable Polymers Based on Renewable Resources, V. Synthesis and Biodegradation Behavior of Poly (ester amide) s Composed of 1, 4:3, 6-Dianhydro-D-glucitol, α-Amino Acid, and Aliphatic Dicarboxylic Acid Units"J. Appl. Polym. Sci.. 81. 2721-2734 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Sato, M.Furuhashi, D.Yang, H.Ohtani, S.Tsuge, M.Okada, K.Tsunoda, K.Aoi: "A Novel Evaluation Method for Biodegradability of Poly (butylene succinate-co-butylene adipate) by Pyrolysis-Gas Chromatography"Polym. Degrad. Stab.. 73. 327-334 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] S.Detchprohm, K.Aoi, M.Okada: "Synthesis of a Novel Chitin Derivative Having Oligo (ε-caprolactone) Side Chains in Aqueous Reaction Media"Macromol. Chem. Phys.. 202. 3560-3570 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Aoi, H.Aoi, M.Okada: "Synthesis of a Poly (vinyl alcohol)-Based Graft Copolymer Having Poly (ε-caprolactone) Side Chains by Solution Polymerization"Macuomol. Chem. Phys.. 203. 1018-1028 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Sato, S.Mizutani, H.Ohtani, S.Tsuge, K.Aoi, T.Seki, M.Okada: "Determination of Degree of Substitution in N-Carboxyethylated Chitin Derivatives by Pyrolysis-Gas Chromaography in the Presence of Oxalic Acid"J. Anal. Appl. Pyrolysis. 64. 177-185 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada, M.Yokoe, K.Aoi: "Biodegradable Polymers Based on Renewable Resources, VI. Synthesis and Biodegradability of Poly (ester carbonate) s Containing 1, 4:3, 6-Dianhydro-D-glucitol and Sebacic Acid Unis"J. Appl. Polym. Sci.. 86. 872-880 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Aoi, A.Takasu, M.Odada, T.Imae: "Nano-scale Molecular Shapes of Water-soluble Chitin Derivatives Having Monodisperse Poly (2-alkyl-2-oxazoline) Side Chains"Macromol. Chem. Phys.. 203. 2650-2657 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada: "Chemical Syntheses of Biodegradable Polymers"Prog. Polym. Sci.. 27. 87-135 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada, K.Aoi: "Biodegradable Polymers from 1, 4:3, 6-Dianhydro-D-glucitol (Isosorbide) and Its Related Compounds"Current Trends in Polymer Science. 7. 57-70 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Yokoe, K.Aoi, M.Okada: "Biodegradable Polymers Based on Renewable Resources, VII. Synthesis of Novel Random and Alternating Copolycarbonates from 1, 4:3, 6-Dianhydrohexitols and Aliphatic Diols"J. Polym. Sci. : Part A : Polym. Chem.. 40. 2312-2321 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada: "Synthesis of Biodegradable Plastics Utilizing Natural Products, Newest Techniques for Green Plastics"CMC. 95 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Okada: "Biodegradabie Polymers Using Sugar Diols Problems and Measures in Modification Techniques and Processing in Biodegradable Plastics"Joho-Gijyutsu Kyoukai.

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

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Published: 2005-04-19  

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