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One-Pot Enzymatic Route to Tetraallyl Ether Functional Oligoesters: Synthesis, UV Curing, and Characterization
KTH, Skolan för bioteknologi (BIO), Biokemi (stängd 20130101).
KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.
KTH, Skolan för bioteknologi (BIO), Biokemi (stängd 20130101).
KTH, Skolan för kemivetenskap (CHE), Fiber- och polymerteknologi, Ytbehandlingsteknik.ORCID-id: 0000-0003-3201-5138
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2010 (Engelska)Ingår i: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 48, nr 23, s. 5289-5297Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

An enzymatic one-pot route in bulk was used to synthesize tetraallyl ether (tAE) functional oligomers based on divinyl adipate, 1,4-butanediol and trimethylolpropane diallyl ether. By using lipase B from Candida antarctica as catalyst and varying the stoichiometric ratio of monomers, it was possible to reach targeted molecular weights (from 1300 to 3300 g mol(-1)) of allyl-ether functional polyesters. The enzyme catalyzed reaction reached completion (>98% conversion based on all monomers) within 24 h at 60 degrees C, under reduced pressure (72 mbar) resulting in similar to 90% yield after filtration. The tAE-functional oligoesters were photopolymerized, without any purification other than removal of the enzyme by filtration, with thiol functional monomers (dithiol, tetrathiol) in a 1: 1 ratio thiol-ene reaction. The photo-initiator, 2,2-dimethoxy-2-phenylacetophenone, was used to improve the rate of reaction under UV light. High conversions (96-99% within detection limits) were found for all thiol-ene films as determined by FT-Raman spectroscopy. The tAE-functional oligoesters were characterized by NMR, MALDI, and SEC. The UV-cured homopolymerized films and the thiol-ene films properties were characterized utilizing DSC and DMTA.

Ort, förlag, år, upplaga, sidor
2010. Vol. 48, nr 23, s. 5289-5297
Nyckelord [en]
CaIB, enzymatic polycondensation, enzymes, films, networks, photopolymerization, polycondensation, polyesters, polyester films, thermoset, thiol-ene, UV curing
Nationell ämneskategori
Polymerkemi
Identifikatorer
URN: urn:nbn:se:kth:diva-14199DOI: 10.1002/pola.24328ISI: 000284225500003Scopus ID: 2-s2.0-78349238609OAI: oai:DiVA.org:kth-14199DiVA, id: diva2:331751
Anmärkning

QC 20100726. Uppdaterad från manuskript till artikel (20101210). Tidigare titel: One-pot enzymatic route to tetraallyl ether functional polyesters: Synthesis, UV curing, and characterization

Tillgänglig från: 2010-07-26 Skapad: 2010-07-26 Senast uppdaterad: 2017-12-12Bibliografiskt granskad
Ingår i avhandling
1. Lipase-Catalyzed Syntheses of Telechelic Polyesters
Öppna denna publikation i ny flik eller fönster >>Lipase-Catalyzed Syntheses of Telechelic Polyesters
2010 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

Telechelic polyesters have successfully been synthesized with lipase-catalyzed polymerization. The produced telechelics had a high degree of di­functionalization, high purity (requiring little or no workup) and controlled degree of polymerization. The syntheses were performed in one-pot one-step reaction systems. The use of protection/deprotection chemistry was not necessary, since the lipase selectivity was utilized in the syntheses. Two different types of lipase-catalyzed polymerizations were applied – ring-opening polymerization and polycondensation. In ring-opening polymerization telechelics were produced by a combination of initiation, α-functionalization, and linking through termination, w-func­tionalization. In polycondensation different types of end-cappers were used to synthesize telechelics. Several exampels of functional groups were used for end-functionalization - epoxide, methacrylate and tetraallyls. Enzyme kinetic schemes describing the different functionalization met­hods of polyesters are presented and discussed. Stoichiometry and different reaction conditions have been studied to understand the effects these functions have on the final structure of the synthesized telechelics. Polyesters are classified as biodegradable, and can also be synthesized from materials that can be extracted or fermented from renewable sources like plants. Lipase-catalysts have several beneficial attributes, like high selectivity, they are renewable and biodegradable, are non-toxic and metal-free and can operate under mild reaction conditions.

The focus of this thesis has been on lipase-catalyzed syntheses and characterization of the produced telechelics, in addition some materials have been produced. Some uses of telechelics are surface modification, materials for block co-polymers, functional films and biomedical applications.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2010. s. 57
Serie
Trita-BIO-Report, ISSN 1654-2312 ; 2010:3
Nyckelord
Candida antarctica lipase B, lipase-catalysis, polymerization, telechelic, functional polyesters, ring-opening polymerization, polycondensation.
Nationell ämneskategori
Medicinsk bioteknologi (med inriktning mot cellbiologi (inklusive stamcellsbiologi), molekylärbiologi, mikrobiologi, biokemi eller biofarmaci)
Identifikatorer
urn:nbn:se:kth:diva-12101 (URN)978-91-7415-574-7 (ISBN)
Disputation
2010-03-26, Svedbegssalen (FD5), Roslagstullsbacken 21, AlbaNova, KTH, Stockholm, 13:00 (Engelska)
Opponent
Handledare
Anmärkning
QC20100726Tillgänglig från: 2010-03-11 Skapad: 2010-03-03 Senast uppdaterad: 2010-12-10Bibliografiskt granskad

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Johansson, MatsMalmström, EvaMartinelle, Mats

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Eriksson, MagnusBoyer, AntoineSinigoi, LorisJohansson, MatsMalmström, EvaHult, KarlTrey, StacyMartinelle, Mats
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Biokemi (stängd 20130101)Ytbehandlingsteknik
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Journal of Polymer Science Part A: Polymer Chemistry
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