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Enzymatically Synthesized Vinyl Ether-Disulfide Monomer Enablingan Orthogonal Combination of Free Radical and Cationic Chemistry toward Sustainable Functional Networks
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0002-0813-0067
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-3201-5138
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0002-8348-2273
2019 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 20, no 3, p. 1308-1316, article id 10.1021/acs.biomac.8b01710Article in journal (Refereed) Published
Abstract [en]

This work demonstrates a versatile and environmentally friendly route for the development of new orthogonal monomers that can be used for postfunctionalizable polymer networks. A monomer containing both vinyl ether (VE) and cyclic disulfide moieties was synthesized via enzyme catalysis under benign reaction conditions. The bifunctional monomer could be polymerized to form macromolecues with differing architectures by the use of either cationic or radical photo polymerization. When cationic polymerization was performed, a linear polymer was obtained with pendant disulfide units in the side chain, whereas in the presence of radical initiator, the VE reacted with the disulfide to yield a branched structure. The monomer was thereafter used to design networks that could be postfunctionalized; the monomer was cross-linked with cationic initiation together with a difunctional VE oligomer and after cross-linking the unreacted disulfides were coupled to RhodamineVE by radical UV-initiation.

Place, publisher, year, edition, pages
2019. Vol. 20, no 3, p. 1308-1316, article id 10.1021/acs.biomac.8b01710
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-249949DOI: 10.1021/acs.biomac.8b01710ISI: 000461270500018OAI: oai:DiVA.org:kth-249949DiVA, id: diva2:1306440
Note

QC 20190425

Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-11-29Bibliographically approved
In thesis
1. Exploring bio-based monomers for UV-curable polymer networks
Open this publication in new window or tab >>Exploring bio-based monomers for UV-curable polymer networks
2019 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Increased environmental awareness and concern has led to a high demand for sustainable, bio-based materials. Consequently, there is a need for research and development of new bio-based polymeric materials that can be synthesized via routes eliminating excessively toxic reactants and by-products. The work presented in this thesis has focused on the utilization of catalysis, mainly enzymatic, and photopolymerization in order to create efficient synthesis of polymeric networks from bio-based monomers.Polyesters from bio-based monomers have been polymerized in bulk and thereafter crosslinked by UV initiation to yield polymer networks with tunable properties. The synthesis was also studied more in detail by varying the different types of catalysts and comparing their effect on the polymer products. Polyesters are a promising class of polymers that can be made from bio-based resources due to the wide range of available bio-based carboxylic acids and alcohols that can be combined to yield many polymers with different properties. However, the synthesis of polyesters is rather time-consuming in order to reach high conversions.As a more efficient alternative, short chain esters monomers and oligomers that have vinyl ether (VE) functionalities were developed. These VE-esters can be synthesized partly from bio-based resources, such as acids, fatty acids and diols, and their synthesis is efficient with enzymatic catalysis. The VE functionality provides a reactive group which can be polymerized rapidly with cationic polymerization. In general, the vinyl ether-esters can be synthesized in less than one hour and crosslinked within a few minutes, which is significantly faster than traditional polyester-synthesis and crosslinking. The enzymatic synthesis of vinyl ether esters also provided a method for developing monomers with orthogonal functionality which was explored by developing functionalizable materials with a variety of macromolecular architectures.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2019. p. 56
Series
TRITA-CBH-FOU ; 2019:30
Keywords
Bio-based, polymers, vinyl ether, polyester, photopolymerization, lipase
National Category
Polymer Chemistry
Research subject
Fibre and Polymer Science
Identifiers
urn:nbn:se:kth:diva-249950 (URN)978-91-7873-195-4 (ISBN)
Public defence
2019-05-24, Kollegiesalen, Brinellvägen 8, Stockholm, 10:00 (English)
Opponent
Supervisors
Available from: 2019-04-25 Created: 2019-04-25 Last updated: 2019-04-26Bibliographically approved

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Johansson, MatsMalmström, Eva

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