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Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Biotechnology (BIO), Industrial Biotechnology.ORCID iD: 0000-0003-2644-0752
KTH, School of Biotechnology (BIO), Industrial Biotechnology.ORCID iD: 0000-0002-2993-9375
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-3201-5138
2014 (English)In: Macromolecular Chemistry and Physics, ISSN 1022-1352, E-ISSN 1521-3935, Vol. 215, no 22, 2198-2206 p.Article in journal (Refereed) Published
Abstract [en]

The use of monomers based on natural materials as a future supply of raw materials has gained more interest in the last decade. Sources ranging from wood to plant oils and algae are exploited as alternatives to traditional fossil-based resources for the synthesis of polymeric materials. The use of these raw materials is not only of interest because of its abundance, but also in terms of price, durability, and/or biodegradability. In the present study, a series of resins utilizing a monomer derived from birch bark is prepared. The thermoset resins are formed by reacting an epoxy-functional omega-hydroxy fatty acid with methacrylate monomers using enzyme catalysis to form multifunctional resins via a one-pot synthesis. The derived oligomers are crosslinked through different polymerization routes to produce thermosets with different properties and/or functionalities. This approach allows natural-based resins with tuned functionalities and mechanical and thermal properties to be obtained.

Place, publisher, year, edition, pages
2014. Vol. 215, no 22, 2198-2206 p.
Keyword [en]
dual curing, enzymatic catalysis, renewable monomers, suberin
National Category
Polymer Technologies
Identifiers
URN: urn:nbn:se:kth:diva-158419DOI: 10.1002/macp.201400192ISI: 000345444200006Scopus ID: 2-s2.0-84913620344OAI: oai:DiVA.org:kth-158419DiVA: diva2:776200
Note

QC 20150107

Available from: 2015-01-07 Created: 2015-01-07 Last updated: 2017-12-05Bibliographically approved
In thesis
1. Telechelic polymers derived from natural resources as building blocks for polymer thermosets
Open this publication in new window or tab >>Telechelic polymers derived from natural resources as building blocks for polymer thermosets
2015 (English)Licentiate thesis, comprehensive summary (Other academic)
Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2015. 39 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2015:13
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-162128 (URN)978-91-7595-469-1 (ISBN)
Presentation
2015-03-27, K1, Teknikringen 56, Stockholm, 13:00 (English)
Opponent
Supervisors
Note

QC 20150323

Available from: 2015-03-23 Created: 2015-03-23 Last updated: 2015-03-25Bibliographically approved
2. Sustainable synthetic pathways towards the formation of bio-based polymeric materials
Open this publication in new window or tab >>Sustainable synthetic pathways towards the formation of bio-based polymeric materials
2016 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Increasing environmental and social awareness arising from the use of oil as main source of raw materials, has awaken the interest of many scientists to explore new synthetic pathways for polymer production. These new approaches embrace the use of alternative feedstock and sustainable synthetic routes aiming for enhancing biodegradability and recyclability. This shift towards more benign strategies is considered positive from different perspectives. Through the exploitation of bio-based feedstock it is possible to minimize the carbon foot print at the same time as new tools for material formation are provided. The use of selective catalysts reduces the formation of side-products, minimizes or avoids the use of solvents and diminish energy consumption. At the same time, new polymeric structures can be formed in terms of functionality and architectures.  

The work herein presented have focused on the development of sustainable synthetic routes for the formation of bio-based polymeric materials with targeted properties. In order to afford this, two bio-sources have been explored for the retrieval of different epoxy-fatty acids, i.e. outer birch bark and vegetable oils. In order to be able to tailor the final material properties and thus be able to target specific applications, we have relied on the selectivity of lipases to preserve the epoxy-functionalities during synthesis. Through the design of specific polymer architectures, e.g. telechelic oligomers, and branched or linear macromers, different degrees of functionality could be prepared. By covalently reacting the epoxy groups through different polymerization techniques, polymer networks were achieved. The proposed synthetic approach resulted in polymeric materials with wide variety of properties ranging from functional networks, to high Tg materials and adhesives, prepared all from renewable sources. This also proved the benefits of the use of lipases in synthesis of polymers for material applications.  

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2016. 61 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2016:38
Keyword
bio-based, polymers, materials
National Category
Polymer Technologies
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-195079 (URN)978-91-7729-173-2 (ISBN)
Public defence
2016-12-02, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

QC 20161101

Available from: 2016-11-01 Created: 2016-11-01 Last updated: 2016-11-11Bibliographically approved
3. 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. 61 p.
Series
TRITA-BIO-Report, ISSN 1654-2312 ; 2017:15
Keyword
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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Semlitsch, StefanMartinelle, MatsJohansson, Mats

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