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

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

Macromolecular bioscience (2007-10-24)
Hiroki Ebata, Kazunobu Toshima, Shuichi Matsumura
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 degrees C. Although poly(12HD) is a highly crystalline polyester having a melting temperature (T(m)) of 87.6 degrees C and crystalline temperature (T(c)) of 64 degrees C, by the copolymerization of 12HD with 12HS, both the T(m) and T(c) 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.

MATERIALS
Product Number
Brand
Product Description

Methyl 12-hydroxystearate, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
12-Hydroxydodecanoic acid, 97%
Sigma-Aldrich
Methyl 12-hydroxystearate, ≥99% (GC)