Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins

Semlitsch, Stefan; Torrón, Susana; Johansson, Mats; Martinelle, Mats

doi:10.1039/c5gc02597d

Cited by 16 publications

(16 citation statements)

References 39 publications

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“…The structure was also confirmed by MALDI‐TOF mass spectrometry (see Figure ) and SEC (see Supporting Information, Figure S3) showing a successful formation of the targeted oligoester with an average DP of 3. More extensive description can be found in the supporting information (Supporting Information, Figure S2 and S3) and ref …”

Section: Resultsmentioning

confidence: 99%

“…Molecular sieves 4 Å (25 wt% of the total amount of monomers) and enzyme (20 wt% of the total amount of monomers) were then added to the solution and the mixture was heated up to 60 °C for 24 h. The catalyst was then removed by filtration and the product used without further purification. A more in‐depth description of this synthesis procedure can be found in a paper focusing on enzyme catalysis in a broader sense …”

Section: Methodsmentioning

confidence: 99%

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Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers

Torrón

Semlitsch

Martinelle

et al. 2014

Macro Chemistry & Physics

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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 ω‐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.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers

Torrón

Semlitsch

Martinelle

et al. 2014

Macro Chemistry & Physics

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“…The use of elevated temperatures leads to undesired ether formation and dehydration of sorbitol or enhances the reactivity of the secondary hydroxy groups leading to the formation of branched polymers as reported in the case of glycerol . More recently the utilization of 9,10‐epoxy‐18‐hydroxyoctadecanoic acid, an epoxy‐functional ω‐hydroxy‐fatty acid extracted from birch bark, for the CaLB‐catalysed synthesis of multifunctional oligoesters (yield >80%, 3.4 < degree of polymerization <4.7) was also reported . The bio‐catalysed synthesis starting from bio‐based monomers containing one or more functionalities such as hydroxy, vinyl and epoxy moieties is a green and sustainable approach when the production of functional pre‐polymers having side or end chain functionalities and a limited molecular weight (up to 8–10 kg mol −1 ) is desired.…”

Section: Enzymo‐catalytic Synthesis Of Functional Bio‐based Polymersmentioning

confidence: 99%

Post‐polymerization modification of bio‐based polymers: maximizing the high functionality of polymers derived from biomass

Farmer

Comerford

Pellis

et al. 2018

Polymer International

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The renaissance of the bio-based chemical industry over the last 20 years has seen an ever growing interest in the synthesis of new bio-based polymers. The building blocks of these new polymers, so called platform molecules, contain significantly more chemical functionality than their petrochemical counterparts (such as ethene, propene and para-xylene). As a result bio-based polymers often contain greater residual chemical functionality in their chains, with groups such as alkenes and hydroxyls commonly observed. These functional groups can act as sites for post-polymerization modification (PPM), thus further extending the range of applications for bio-based polymers by tailoring the polymers' final properties. This mini-review highlights some of the most recent and compelling examples of how to make use of bio-based polymers with residual functional groups for PPM. It also looks at how the emerging interdisciplinary field of enzymatic polymer synthesis allows for increased functionality in polymers by avoiding side-reactions as a result of milder reaction conditions, and additionally offers an alternative means of polymer surface modification.

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“…For instance, although PCL is mainly derived from commercial nonrenewable ε-caprolactone (ε-CL), a two-step pathway starting from 5-HMF platform can yield bio-sourced ε-CL and potentially opens opportunities to create bio-based PCL [17]. Furthermore, Novozym 435 (an immobilized Candida antarctica lipase B, CaLB) is the benchmark enzyme that is extensively investigated as a catalyst for polycondensation and for enzymatic ring opening polymerization (eROP) reactions in the bulk and in organic media [23][24][25]. Novozym 435 is known to exhibit partial regioselectivity towards primary alcohols.…”

Section: Introductionmentioning

confidence: 99%

Novel green route towards polyesters-based resin by photopolymerization of star polymers

Baheti¹,

Bonneaud²,

Bouilhac³

et al. 2019

Express Polym. Lett.

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Bio-based star-shaped poly(ε-caprolactone)s (S-PCL) derived from sugar-based D-sorbitol as an initiator were obtained via solvent-free enzymatic ring-opening polymerization (eROP). The star S-PCL were converted into UV-curable maleates by employing maleic anhydride for subsequent crosslinking with tri(ethylene glycol) divinyl ether (DVE-3) in the presence of Darocur 1173 as a radical photoinitiator. The kinetics of the UV-induced radical copolymerization was monitored by real-time Fourier-Transform InfraRed (FTIR) spectroscopy, which revealed that the star S-PCL maleate/divinyl ether system was not scavenged by molecular oxygen (donor/acceptor polymerization). The UV-crosslinking reaction was fast (~10 s) to reach near quantitative conversions. The S-PCL maleate / divinyl ether liquid formulation cast on glass substrates successfully gave films upon UV-crosslinking. The thermal properties of the polymer films and their precursor polymers were characterized by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Finally, the crosslinked polymer film demonstrated promising adhesive properties on steel, aluminum and glass substrates.

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Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins

Abstract: Candida antarctica lipase B (CalB) was used as a chemoselective catalyst for the synthesis of multifunctional oligoester resins based on an epoxy-functional ω-hydroxy-fatty acid (EFA) extracted from birch bark.

Cited by 16 publications

References 39 publications

Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers

Polymer Thermosets from Multifunctional Polyester Resins Based on Renewable Monomers

Post‐polymerization modification of bio‐based polymers: maximizing the high functionality of polymers derived from biomass

Novel green route towards polyesters-based resin by photopolymerization of star polymers

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