Lipase-catalyzed synthesis and properties of poly[(12-hydroxydodecanoate)- co-(12-hydroxystearate)] directed towards novel green and sustainable elastomers

Hiroki Ebata, Kazunobu Toshima, Shuichi Matsumura

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Novel green and sustainable elastomers having both good biodegradability and chemical recyclability properties were designed and synthesized using potentially biobased materials and lipase as an environmentally benign catalyst. High molecular weight poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] [poly(12HD-co-12HS)] samples with varying monomer ratios were prepared by the polycondensation of 12-hydroxydodecanoic acid and methyl 12-hydroxystearate using immobilized lipase from Candida antarctica (IM-CA) in toluene in the presence of molecular sieves 4A at 90°C. Although poly(12HD) is a highly crystalline polyester having a melting temperature (Tm) of 87.6°C and crystalline temperature (Tc) of 64°C, by the copolymerization of 12HD with 12HS, both the Tm and Tc of the copolymer decreased with increasing 12HS contents, and poly(12HD-co- 12HS) containing more than 60 mol-% 12HS was a viscous liquid at room temperature. At the same time, the Young's modulus and hardness also decreased with increasing 12HS content, and poly(12HD-co-36 mol-% 12HS) exhibited an elastic behavior, having a hardness of 70 A using a durometer A. In addition, it showed an excellent biodegradability by activated sludge and chemical recyclability by lipase. (Chemical Equation Presented)

Original languageEnglish
Pages (from-to)38-45
Number of pages8
JournalMacromolecular Bioscience
Volume8
Issue number1
DOIs
Publication statusPublished - 2008 Jan 9

Fingerprint

Elastomers
Lipases
Lipase
Biodegradability
Temperature
Hardness
Crystalline materials
Polyesters
Candida
Molecular sieves
Toluene
Polycondensation
Copolymerization
Chemical properties
Melting point
Elastic Modulus
Copolymers
Sewage
Monomers
Elastic moduli

Keywords

  • Biodegradability
  • Elastomer
  • Lipase
  • Poly(12- hydroxydodecanoate-co-12-hydroxystearate)
  • Polycondensation

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry
  • Bioengineering

Cite this

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abstract = "Novel green and sustainable elastomers having both good biodegradability and chemical recyclability properties were designed and synthesized using potentially biobased materials and lipase as an environmentally benign catalyst. High molecular weight poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] [poly(12HD-co-12HS)] samples with varying monomer ratios were prepared by the polycondensation of 12-hydroxydodecanoic acid and methyl 12-hydroxystearate using immobilized lipase from Candida antarctica (IM-CA) in toluene in the presence of molecular sieves 4A at 90°C. Although poly(12HD) is a highly crystalline polyester having a melting temperature (Tm) of 87.6°C and crystalline temperature (Tc) of 64°C, by the copolymerization of 12HD with 12HS, both the Tm and Tc of the copolymer decreased with increasing 12HS contents, and poly(12HD-co- 12HS) containing more than 60 mol-{\%} 12HS was a viscous liquid at room temperature. At the same time, the Young's modulus and hardness also decreased with increasing 12HS content, and poly(12HD-co-36 mol-{\%} 12HS) exhibited an elastic behavior, having a hardness of 70 A using a durometer A. In addition, it showed an excellent biodegradability by activated sludge and chemical recyclability by lipase. (Chemical Equation Presented)",
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N2 - Novel green and sustainable elastomers having both good biodegradability and chemical recyclability properties were designed and synthesized using potentially biobased materials and lipase as an environmentally benign catalyst. High molecular weight poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] [poly(12HD-co-12HS)] samples with varying monomer ratios were prepared by the polycondensation of 12-hydroxydodecanoic acid and methyl 12-hydroxystearate using immobilized lipase from Candida antarctica (IM-CA) in toluene in the presence of molecular sieves 4A at 90°C. Although poly(12HD) is a highly crystalline polyester having a melting temperature (Tm) of 87.6°C and crystalline temperature (Tc) of 64°C, by the copolymerization of 12HD with 12HS, both the Tm and Tc of the copolymer decreased with increasing 12HS contents, and poly(12HD-co- 12HS) containing more than 60 mol-% 12HS was a viscous liquid at room temperature. At the same time, the Young's modulus and hardness also decreased with increasing 12HS content, and poly(12HD-co-36 mol-% 12HS) exhibited an elastic behavior, having a hardness of 70 A using a durometer A. In addition, it showed an excellent biodegradability by activated sludge and chemical recyclability by lipase. (Chemical Equation Presented)

AB - Novel green and sustainable elastomers having both good biodegradability and chemical recyclability properties were designed and synthesized using potentially biobased materials and lipase as an environmentally benign catalyst. High molecular weight poly[(12-hydroxydodecanoate)-co-(12-hydroxystearate)] [poly(12HD-co-12HS)] samples with varying monomer ratios were prepared by the polycondensation of 12-hydroxydodecanoic acid and methyl 12-hydroxystearate using immobilized lipase from Candida antarctica (IM-CA) in toluene in the presence of molecular sieves 4A at 90°C. Although poly(12HD) is a highly crystalline polyester having a melting temperature (Tm) of 87.6°C and crystalline temperature (Tc) of 64°C, by the copolymerization of 12HD with 12HS, both the Tm and Tc of the copolymer decreased with increasing 12HS contents, and poly(12HD-co- 12HS) containing more than 60 mol-% 12HS was a viscous liquid at room temperature. At the same time, the Young's modulus and hardness also decreased with increasing 12HS content, and poly(12HD-co-36 mol-% 12HS) exhibited an elastic behavior, having a hardness of 70 A using a durometer A. In addition, it showed an excellent biodegradability by activated sludge and chemical recyclability by lipase. (Chemical Equation Presented)

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