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One-pot enzymatic route to tetraallyl ether functional oligoesters: Synthesis, UV curing, and characterization

Authors

  • Magnus Eriksson,

    1. Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden
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  • Antoine Boyer,

    1. Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
    2. Department of Material Engineering, Politecnico di Torino, Corso Duca degli Abruzzi 24, 10129 Torino, Italy
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  • Loris Sinigoi,

    1. Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden
    2. Laboratory of Applied and Computational Biocatalysis, Department of Pharmaceutical Sciences, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy
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  • Mats Johansson,

    1. Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
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  • Eva Malmström,

    1. Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
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  • Karl Hult,

    1. Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden
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  • Stacy Trey,

    Corresponding author
    1. Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
    2. SP Trätek, Technical Research Institute of Sweden, Drottning Kristinas väg 67, Stockholm 114-86
    • Department of Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
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  • Mats Martinelle

    Corresponding author
    1. Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden
    • Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden
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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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