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Chemo- enzymatic pathways toward pinene- based renewable materials
KTH, Centres, Science for Life Laboratory, SciLifeLab. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-8727-2102
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0003-1029-5992
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Centres, Wallenberg Wood Science Center. KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0002-9572-6888
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2019 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 21, no 10, p. 2720-2731Article in journal (Refereed) Published
Abstract [en]

Sobrerol methacrylate (SobMA) was synthesized and subsequently polymerized using different chemical and enzymatic routes. Sobrerol was enzymatically converted from -pinene in a small model scale by a Cytochrome P450 mutant from Bacillus megaterium. Conversion of sobrerol into SobMA was performed using both classical ester synthesis, i.e., acid chloride-reactions in organic solvents, and a more green approach, the benign lipase catalysis. Sobrerol was successfully esterified, leaving the tertiary alcohol and ene to be used for further chemistry. SobMA was polymerized into PSobMA using different radical polymerization techniques, including free radical (FR), controlled procedures (Reversible Addition Fragmentation chain-Transfer polymerization, (RAFT) and Atom Transfer Radical Polymerization (ATRP)) as well as by enzyme catalysis (horseradish peroxidase-mediated free radical polymerization). The resulting polymers showed high glass-transition temperatures (T-g) around 150 degrees C, and a thermal degradation onset above 200 degrees C. It was demonstrated that the T-g could be tailored by copolymerizing SobMa with appropriate methacrylate monomers and that the Flory-Fox equation could be used to predict the T-g. The versatility of PSobMA was further demonstrated by forming crosslinked thin films, either using the ene'-functionality for photochemically initiated thiol-ene'-chemistry, or reacting the tertiary hydroxyl-group with hexamethoxymethylmelamine, as readily used for thermally curing coatings systems.

Place, publisher, year, edition, pages
2019. Vol. 21, no 10, p. 2720-2731
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Polymer Technologies Polymer Chemistry
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URN: urn:nbn:se:kth:diva-252972DOI: 10.1039/c9gc00718kISI: 000468627800016Scopus ID: 2-s2.0-85066853137OAI: oai:DiVA.org:kth-252972DiVA, id: diva2:1342051
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QC 20190812

Available from: 2019-08-12 Created: 2019-08-12 Last updated: 2019-08-12Bibliographically approved

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Stamm, ArneTengdelius, MattiasSchmidt, BjörnEngström, JoakimSyrén, Per-OlofFogelström, LindaMalmström, Eva

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Stamm, ArneTengdelius, MattiasSchmidt, BjörnEngström, JoakimSyrén, Per-OlofFogelström, LindaMalmström, Eva
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Science for Life Laboratory, SciLifeLabCoating TechnologyFibre- and Polymer TechnologyWallenberg Wood Science CenterVinnExcellence Center BiMaC Innovation
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