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One-pot enzyme-catalyzed synthesis of dual-functional polyester macromers towards surface active hydrophobic films
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Biotechnology (BIO), Industrial Biotechnology.
KTH, School of Biotechnology (BIO), Industrial Biotechnology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
(English)Manuscript (preprint) (Other academic)
Abstract [en]

Selective enzyme catalysis is a valuable tool for the processing of monomers into value-added materials. In the present study natural resources were used to retrieve an ω-hydroxy fatty acid monomer containing an epoxide functionality. A procedure was developed for the synthesis of dual-functional oligomers by utilizing lipase catalysis in a one-pot synthesis route. The chemoselectivity of the enzyme allowed addition of thiol monomers to the retrieved epoxy monomers, without harming the epoxides, achieving a thiol-epoxy functional polyester resin. The synthesis reached full conversion (>99 %) after 8 h. It was possible to selectively crosslink the resin, through UV-initiated cationic polymerization of the epoxides into thiol-functional thermosets. The curing performance was followed in situ by Real-Time FTIR. The thiol groups on the surface of the film were accessible for post-modification.

National Category
Polymer Chemistry Biocatalysis and Enzyme Technology
Research subject
Chemistry; Biotechnology
Identifiers
URN: urn:nbn:se:kth:diva-212428OAI: oai:DiVA.org:kth-212428DiVA, id: diva2:1134803
Note

QC 20170822

Available from: 2017-08-21 Created: 2017-08-21 Last updated: 2017-08-23Bibliographically approved
In thesis
1. Building blocks for polymer synthesis by enzymatic catalysis
Open this publication in new window or tab >>Building blocks for polymer synthesis by enzymatic catalysis
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The search for alternatives to oil-based monomers has sparked interest for scientists to focus on the use of renewable resources for energy production, for the synthesis of polymeric materials and in other areas. With the use of renewable resources, scientists face new challenges to first isolate interesting molecules and then to process them.

Enzymes are nature’s own powerful catalysts and display a variety of activities. They regulate important functions in life. They can also be used for chemical synthesis due to their efficiency, selectivity and mild reaction conditions. The selectivity of the enzyme allows specific reactions enabling the design of building blocks for polymers.

In the work presented here, a lipase (Candida antarctica lipase B (CalB)) was used to produce building blocks for polymers. An efficient route was developed to selectively process epoxy-functional fatty acids into resins with a variety of functional groups (maleimide, oxetane, thiol, methacrylate). These oligoester structures, based on epoxy fatty acids from birch bark and vegetable oils, could be selectively cured to form thermosets with tailored properties.

The specificity of an esterase with acyl transfer activity from Mycobacterium smegmatis (MsAcT) was altered by rational design. The produced variants increased the substrate scope and were then used to synthesize amides in water, where the wild type showed no conversion. A synthetic procedure was developed to form mixed dicarboxylic esters by selectively reacting only one side of divinyl adipate in order to introduce additional functional groups.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2017. p. 61
Series
TRITA-BIO-Report, ISSN 1654-2312 ; 2017:15
Keywords
Enzyme, Enzyme Engineering, Biocatalysis, Lipase, CalB, MsAcT, Substrate specificity, Selectivity, Polymer Chemistry, Polymer Synthesis
National Category
Biocatalysis and Enzyme Technology
Research subject
Biotechnology
Identifiers
urn:nbn:se:kth:diva-212499 (URN)978-91-7729-494-8 (ISBN)
Public defence
2017-09-22, Kollegiesalen, Brinellvägen 8, Stockholm, 10:00
Opponent
Supervisors
Note

QC 20170823

Available from: 2017-08-23 Created: 2017-08-22 Last updated: 2017-08-23Bibliographically approved

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