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

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...

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Bibliographic Details
Published in:Journal of Polymer Science Part A: Polymer Chemistry
Main Authors: Eriksson, Magnus, Boyer, Antoine, Sinigoi, Loris, Johansson, Mats, Malmström, Eva, Hult, Karl, Trey, Stacy, Martinelle, Mats
Other Authors: The KAMI Research Foundation, BiMaC, IRENE, In silico Rational Engineering of Novel Enzymes, LLP Erasmus Placement Programme, Swedish Research Council
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2010
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/pola.24328
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fpola.24328
https://onlinelibrary.wiley.com/doi/pdf/10.1002/pola.24328
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Summary: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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