Article

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

  1. Magnus Eriksson1,
  2. Antoine Boyer2,3,
  3. Loris Sinigoi1,4,
  4. Mats Johansson2,
  5. Eva Malmström2,
  6. Karl Hult1,
  7. Stacy Trey2,5,*,
  8. Mats Martinelle1,*

Article first published online: 1 OCT 2010

DOI: 10.1002/pola.24328

Issue

Journal of Polymer Science Part A: Polymer Chemistry

Journal of Polymer Science Part A: Polymer Chemistry

Volume 48, Issue 23, pages 5289–5297, 1 December 2010

Additional Information

How to Cite

Eriksson, M., Boyer, A., Sinigoi, L., Johansson, M., Malmström, E., Hult, K., Trey, S. and Martinelle, M. (2010), One-pot enzymatic route to tetraallyl ether functional oligoesters: Synthesis, UV curing, and characterization. J. Polym. Sci. A Polym. Chem., 48: 5289–5297. doi: 10.1002/pola.24328

Author Information

  1. 1

    Department of Biochemistry, School of Biotechnology, KTH, Royal Institute of Technology, SE-106 91 Stockholm, Sweden

  2. 2

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

  3. 3

    Department of Material Engineering, Politecnico di Torino, Corso Duca degli Abruzzi 24, 10129 Torino, Italy

  4. 4

    Laboratory of Applied and Computational Biocatalysis, Department of Pharmaceutical Sciences, University of Trieste, Piazzale Europa 1, 34127 Trieste, Italy

  5. 5

    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

Publication History

  1. Issue published online: 28 OCT 2010
  2. Article first published online: 1 OCT 2010
  3. Manuscript Accepted: 18 AUG 2010
  4. Manuscript Received: 13 MAR 2010

Funded by

  • The KAMI Research Foundation
  • BiMaC (Biofibre Materials Centre). Grant Number: FP7-KBBE-2008-2B
  • IRENE, In silico Rational Engineering of Novel Enzymes. Grant Number: 227279
  • LLP Erasmus Placement Programme
  • Swedish Research Council (VR)

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Keywords:

  • CalB;
  • enzymatic polycondensation;
  • enzymes;
  • films;
  • networks;
  • photopolymerization;
  • polycondensation;
  • polyesters;
  • polyester films;
  • thermoset;
  • thiol-ene;
  • UV curing

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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