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New functionalized polyesters to achieve controlled architectures
KTH, Superseded Departments, Polymer Technology.ORCID iD: 0000-0002-1922-128X
KTH, Superseded Departments, Polymer Technology.
2004 (English)In: Journal of Polymer Science Part A: Polymer Chemistry, ISSN 0887-624X, E-ISSN 1099-0518, Vol. 42, no 3, 444-452 p.Article in journal (Refereed) Published
Abstract [en]

Following our continued interest in the production of bioerodible and biodegradable functional polymers for biomedical applications, we synthesized and characterized new unsaturated polyesters. The presence of functional groups in the polymer backbone provided sites for chemical modification, and through a variation in the structure, the physical properties, such as the hydrophilicity and solubility, could be affected. With 1,1-di-n-butyl-stanna-2,7-dioxacyclo-4-heptene as the initiator in the ring-opening polymerization of polyesters, a new set of functionalized polyesters was created. The polymerization of epsilon-caprolactone resulted in poly(epsilon-caprolactone) with a double bond incorporated into the structure. The polymers were obtained in a controlled manner with low molecular dispersities. The double bond was previously incorporated into L-lactide polymers, and the two reactions were compared in this study. The conversion of E-caprolactone, with a degree of polymerization of 50, was completed within 140 min, whereas for L-lactide, only a 45% conversion took place in the same period of time. The dispersities were somewhat higher with E-caprolactone because of the higher reaction rate and, therefore, lower selectivity. The incorporated C-C double bond in the polyesters provided a variety of opportunities for further modifications. In this case, the double bond of the L-lactide macromonomers was oxidized into epoxides. Epoxidation was carried out with m-chloroperoxybenzoic acid as a chemical reagent. The conversion of the double bonds into epoxides was completed, and the obtained yields were good (>95%). As a result of the mild reaction conditions, the epoxidation of the double bond was carried out quantitatively without any side reactions.

Place, publisher, year, edition, pages
2004. Vol. 42, no 3, 444-452 p.
Keyword [en]
ring-opening polymerization, polyesters, functionalization of polymers, double bond, epoxidation, UNSATURATED SIDE-CHAINS, BACTERIAL POLYESTERS, EPSILON-CAPROLACTONE, BIOMEDICAL APPLICATIONS, CHEMICAL-MODIFICATION, ALIPHATIC POLYESTERS, L-LACTIDE, POLYMERIZATION, POLYMERS
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-13187DOI: 10.1002/pola.10805ISI: 000188197200007Scopus ID: 2-s2.0-0742272592OAI: oai:DiVA.org:kth-13187DiVA: diva2:321694
Note
QC 20100602Available from: 2010-06-02 Created: 2010-06-02 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Novel Possibilities for Advanced Molecular Structure Design for Polymers and Networks
Open this publication in new window or tab >>Novel Possibilities for Advanced Molecular Structure Design for Polymers and Networks
2003 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Synthetic and degradable polymers are an attractive choicein many areas, since it is possible to control the way in whichthey are manufactured; more specifically, pathways tomanipulate the architecture, the mechanical properties and thedegradation times have been identified. In this work,L-lactide, 1,5-dioxepan-2-one and ε-caprolactone were usedas monomers to synthesize polymers with different architecturesby ring-opening polymerization. By using novel initiators,triblock copolymers, functionalized linear macromonomers andstar-shaped aliphatic polyesters with well-defined structureshave been synthesized. To synthesize triblock copolymers,cyclic germanium initiators were studied. The polymerizationproceeded in a controlled manner although the reaction rateswere low. To introduce functionality into the polymer backbone,functionalized cyclic tin alkoxides were prepared and used asinitiators. During the insertion-coordination polymerization,the initiator fragment consisting mainly of a double bond wasincorporated into the polymer backbone. The double bond wasalso successfully epoxidized and this gave unique possibilitiesof synthesizing graft polymers with precise spacing. Themacromonomer technique is a very effective method for producingwell-defined graft polymers. Spirocyclic tin initiators weresynthesized and used to construct star-shaped polymers. Thestar-shaped polymers were subsequently crosslinked in apolycondensation reaction. These crosslinked structures swelledin water, and swelling tests showed that by changing thestructure of the hydrogel network, the degree of swelling canbe altered. A first evaluation of the surface characteristicsof the linear triblock copolymers was also performed. AFManalysis of the heat-treated surfaces revealed nanometer-scalefibers and tests showed that keratinocytes were able to growand proliferate on these surfaces.

Place, publisher, year, edition, pages
Stockholm: KTH, 2003. 78 p.
Keyword
ring-opening polymerization, coordination-insertion, germanium, cyclic tin alkoxides, spirocyclic initiators, poly(L-lactide), poly(1, 5-dioxepan-2-one), triblock, star-shaped, network, functionalization, morphology, AFM
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-3623 (URN)91-7283-577-X (ISBN)
Public defence
2003-10-31, 00:00 (English)
Note
QC 20100602Available from: 2003-10-28 Created: 2003-10-28 Last updated: 2010-06-02Bibliographically approved

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