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Enzymatic One-Pot Route to Telechelic Polypentadecalactone Epoxide: Synthesis, UV Curing, and Characterization
KTH, School of Biotechnology (BIO), Biochemistry.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-7132-3251
KTH, School of Biotechnology (BIO), Biochemistry.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0002-8348-2273
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2009 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 10, no 11, 3108-3113 p.Article in journal (Refereed) Published
Abstract [en]

In an enzymatic one-pot procedure immobilized lipase B from Candida antarctica was used to synthesize semicrystalline diepoxy functional macromonomers based on glycidol, pentadecalactone, and adipic acid. By changing the stoichiometry of the building blocks. macromonomers of controlled molecular weight front 1400 to 2700 g mol(-1) could be afforded. The enzyme-catalyzed reaction went to completion (conversion >= 95%) within 24 h at 60 degrees C. After removal of the enzyme, the produced macromonomers were used for photopolymerization without any purification. The macromonomers readily copolymerized cationically with a cycloaliphatic diepoxide (Cyracure UVR-6110; CA-dE) to high conversion. The cross-linked copolymers formed a durable film with a degree of crystallinity depending on the macromonomer size and amount of CA-dE used, without CA-dE the macromonomers homopolymerized only to a low degree. Combined with CA-dE conversions of 85-90% were determined by FT-Raman spectroscopy. The films became more durable once reinforced with CA-dE, increasing the cross-link density and reducing the crystallinity of the PDL segments in the films.

Place, publisher, year, edition, pages
2009. Vol. 10, no 11, 3108-3113 p.
Keyword [en]
RING-OPENING POLYMERIZATION, LIPASE-CATALYZED SYNTHESIS, POLY(OMEGA-PENTADECALACTONE), THIOL, POLY(EPSILON-CAPROLACTONE), POLYESTERS, ADHESIVES, NETWORKS, SOLVENT, ACID
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-12149DOI: 10.1021/bm9007925ISI: 000271428800019Scopus ID: 2-s2.0-70449500927OAI: oai:DiVA.org:kth-12149DiVA: diva2:303104
Note
QC20100723Available from: 2010-03-11 Created: 2010-03-11 Last updated: 2010-07-26Bibliographically approved
In thesis
1. Lipase-Catalyzed Syntheses of Telechelic Polyesters
Open this publication in new window or tab >>Lipase-Catalyzed Syntheses of Telechelic Polyesters
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Stockholm: KTH, 2010. 57 p.
Series
Trita-BIO-Report, ISSN 1654-2312 ; 2010:3
Keyword
Candida antarctica lipase B, lipase-catalysis, polymerization, telechelic, functional polyesters, ring-opening polymerization, polycondensation.
National Category
Medical Biotechnology (with a focus on Cell Biology (including Stem Cell Biology), Molecular Biology, Microbiology, Biochemistry or Biopharmacy)
Identifiers
urn:nbn:se:kth:diva-12101 (URN)978-91-7415-574-7 (ISBN)
Public defence
2010-03-26, Svedbegssalen (FD5), Roslagstullsbacken 21, AlbaNova, KTH, Stockholm, 13:00 (English)
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Note
QC20100726Available from: 2010-03-11 Created: 2010-03-03 Last updated: 2010-12-10Bibliographically approved

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Fogelström, LindaMalmström, EvaJohansson, MatsMartinelle, Mats

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