One‐pot enzymatic route to tetraallyl ether functional oligoesters: Synthesis,UV curing,and characterization |
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| Authors: | Magnus Eriksson Antoine Boyer Loris Sinigoi Mats Johansson Eva Malmström Karl Hult Stacy Trey Mats Martinelle |
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| Institution: | 1. Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE‐106 91 Stockholm, Sweden;2. Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE‐100 44 Stockholm, Sweden;3. Department of Material Engineering, Politecnico di Torino, Corso Duca degli Abruzzi 24, 10129 Torino, Italy;4. Laboratory of Applied and Computational Biocatalysis, Department of Pharmaceutical Sciences, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy;5. SP Tr?tek, Technical Research Institute of Sweden, Drottning Kristinas v?g 67, Stockholm 114‐86 |
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| Abstract: | An enzymatic one‐pot route in bulk was used to synthesize tetraallyl ether (tAE) functional oligomers based on divinyl adipate, 1,4‐butanediol and trimethylolpropane diallyl ether. By using lipase B from Candida antarctica as catalyst and varying the stoichiometric ratio of monomers, it was possible to reach targeted molecular weights (from 1300 to 3300 g mol?1) of allyl‐ether functional polyesters. The enzyme catalyzed reaction reached completion (>98% conversion based on all monomers) within 24 h at 60 °C, under reduced pressure (72 mbar) resulting in ～90% yield after filtration. The tAE‐functional oligoesters were photopolymerized, without any purification other than removal of the enzyme by filtration, with thiol functional monomers (dithiol, tetrathiol) in a 1:1 ratio thiol‐ene reaction. The photo‐initiator, 2,2‐dimethoxy‐2‐phenylacetophenone, was used to improve the rate of reaction under UV light. High conversions (96–99% within detection limits) were found for all thiol‐ene films as determined by FT‐Raman spectroscopy. The tAE‐functional oligoesters were characterized by NMR, MALDI, and SEC. The UV‐cured homopolymerized films and the thiol‐ene films properties were characterized utilizing DSC and DMTA. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010 |
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| Keywords: | CalB enzymatic polycondensation enzymes films networks photopolymerization polycondensation polyesters polyester films thermoset thiol‐ene UV curing |
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