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Polymers 2012, 4(1), 486-500; doi:10.3390/polym4010486

Enzymatic Synthesis and Crosslinking of Novel High Molecular Weight Polyepoxyricinoleate

Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
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Received: 9 January 2012 / Revised: 24 January 2012 / Accepted: 30 January 2012 / Published: 10 February 2012
(This article belongs to the Special Issue Enzymes in Monomer and Polymer Synthesis)
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Abstract

Methyl epoxyricinoleate was prepared in high yield by the lipase-catalyzed epoxidation of methyl ricinoleate with H2O2. A high molecular weight polyepoxyricinoleate (PER) with a maximum weight average molecular weight (Mw) of 272,000 was enzymatically prepared by the polycondensation of methyl epoxyricinoleate using immobilized lipase from Burkholderia cepacia (lipase PS-IM) in bulk at 80 °C for 5 d. PER showed good low temperature fluidability. PER was readily cured by maleic anhydride (MA) at 80 °C to produce a chloroform-insoluble PER-MA film. Both the glass transition temperature and Young’s modulus increased with increasing MA content and PER Mw. In contrast, the elongation at break decreased with increasing MA content and PER Mw. Methyl epoxyricinoleate, PER and PER-MA showed biodegradability by activated sludge, and that of the PER-MA film decreased with increasing MA content.
Keywords: enzyme-catalyzed epoxidation; enzyme-catalyzed polymerization; biobased elastomer; green polymer; ricinoleic acid; epoxyricinoleic acid; polyepoxyricinoleate enzyme-catalyzed epoxidation; enzyme-catalyzed polymerization; biobased elastomer; green polymer; ricinoleic acid; epoxyricinoleic acid; polyepoxyricinoleate
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Kazariya, A.; Matsumura, S. Enzymatic Synthesis and Crosslinking of Novel High Molecular Weight Polyepoxyricinoleate. Polymers 2012, 4, 486-500.

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