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Sustainable synthetic pathways towards the formation of bio-based polymeric materials
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
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 [en]
bio-based, polymers, materials
National Category
Polymer Technologies
Research subject
Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-195079ISBN: 978-91-7729-173-2 (print)OAI: oai:DiVA.org:kth-195079DiVA: diva2:1043975
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
List of papers
1. Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins
Open this publication in new window or tab >>Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins
2016 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 18, no 7, 1923-1929 p.Article in journal (Refereed) Published
Abstract [en]

The use of enzymes as selective catalysts for processing renewable monomers into added value polymers and materials has received increased attention during the last decade. In the present work Candida antarctica lipase B (CalB) was used as catalyst in one-pot routes to synthesise multifunctional oligoester resins based on an epoxy-functional omega-hydroxy-fatty acid (EFA) extracted from birch bark. The chemoselective enzymatic process resulted in three different EFA-based telechelic oligomers with targeted molecular weights; containing maleimide, methacrylate or oxetane as end-groups, respectively. The enzyme catalysed synthesis of the maleimide and the oxetane telechelic oligomers reached full conversion of monomers (>95%) after 2 h. In the case of methacrylate functional oligomer the EFA monomer reached full conversion (>98%) after 2 h but the integration of the methacrylate moiety took more than 10 h. This was due to a rate limiting reaction path using ethylene glycol dimethacrylate as substrate. The oligomer products were characterised by NMR, MALDI-TOF-MS and SEC.

Place, publisher, year, edition, pages
The Royal Society of Chemistry, 2016
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-185665 (URN)10.1039/c5gc02597d (DOI)000372981400012 ()2-s2.0-84962377189 (ScopusID)
Funder
EU, FP7, Seventh Framework Programme
Note

QC 20160426

Available from: 2016-04-26 Created: 2016-04-25 Last updated: 2016-11-01Bibliographically approved
2. Tailoring soft polymer networks based on sugars and fatty acids towards pressure sensitive adhesive applications
Open this publication in new window or tab >>Tailoring soft polymer networks based on sugars and fatty acids towards pressure sensitive adhesive applications
(English)Manuscript (preprint) (Other academic)
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-194794 (URN)
Note

QC 20161101

Available from: 2016-10-31 Created: 2016-10-31 Last updated: 2016-11-01Bibliographically approved
3. Oxetane-Terminated Telechelic Epoxy-Functional Polyesters as Cationically Polymerizable Thermoset Resins: Tuning the Reactivity with Structural Design
Open this publication in new window or tab >>Oxetane-Terminated Telechelic Epoxy-Functional Polyesters as Cationically Polymerizable Thermoset Resins: Tuning the Reactivity with Structural Design
2015 (English)In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 53, no 19, 2258-2266 p.Article in journal (Refereed) Published
Abstract [en]

A series of epoxy-functional telechelic oligomers containing oxetane end groups have been synthesized. The precursor monomer, extracted from outer Birch bark, was first polymerized through enzyme-catalyzed esterification to form oligomers having epoxy and/or oxetane groups in the structures. The oligoesters were subsequently crosslinked through cationic polymerization either by epoxy or oxetane homopolymerization or copolymerization when both functionalities were present. A study of the polymerizations of the resins was performed "in situ" using real-time Fourier transform infrared spectroscopy revealing a preferred copolymerization when compared with the homopolymerization. By tailoring the different structures, it was possible to control the final mechanical properties of the networks.

Place, publisher, year, edition, pages
[Torron, Susana; Johansson, Mats] KTH Royal Inst Technol, Div Coating Technol, Sch Chem Sci & Engn, Dept Fibre & Polymer Technol, SE-10044 Stockholm, Sweden.: , 2015
Keyword
biobased monomer, cationic polymerization, enzymatic catalysis, enzymes, epoxide, oxetane, telechelic polymers
National Category
Polymer Technologies
Identifiers
urn:nbn:se:kth:diva-174215 (URN)10.1002/pola.27673 (DOI)000360729600008 ()2-s2.0-84942295531 (ScopusID)
Note

QC 20151016

Available from: 2015-10-16 Created: 2015-10-02 Last updated: 2016-11-01Bibliographically approved
4. Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers
Open this publication in new window or tab >>Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers
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.

Keyword
dual curing, enzymatic catalysis, renewable monomers, suberin
National Category
Polymer Technologies
Identifiers
urn:nbn:se:kth:diva-158419 (URN)10.1002/macp.201400192 (DOI)000345444200006 ()2-s2.0-84913620344 (ScopusID)
Note

QC 20150107

Available from: 2015-01-07 Created: 2015-01-07 Last updated: 2016-12-01Bibliographically approved
5. Biocatalytic synthesis of epoxy resins from fatty acids as a versatile route for the formation of polymer thermosets with tunable properties
Open this publication in new window or tab >>Biocatalytic synthesis of epoxy resins from fatty acids as a versatile route for the formation of polymer thermosets with tunable properties
(English)Manuscript (preprint) (Other academic)
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-194793 (URN)
Note

QC 20161101

Available from: 2016-10-31 Created: 2016-10-31 Last updated: 2016-11-01Bibliographically approved

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The full text will be freely available from 2017-11-11 15:12
Available from 2017-11-11 15:12

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