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Design of Elastomeric Homo- and Copolymer Networks of Functional Aliphatic Polyester for Use in Biomedical Applications
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.ORCID iD: 0000-0002-1922-128X
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Polymer Technology.
2010 (English)In: Chemistry of Materials, ISSN 0897-4756, E-ISSN 1520-5002, Vol. 22, no 9, 3009-3014 p.Article in journal (Refereed) Published
Abstract [en]

An unsaturated aliphatic polyester was synthesized by condensation polymerization to yield the pre-polymer, poly(but-2-ene-1,4-diyl malonate) (PBM), which is applicable as an elastomeric network and as a macroinitiator for the polymerization of cyclic ester monomers. The method of preparation was simple and straightforward with no need to purify the monomers or add a potentially harmful catalyst. The number average molecular weight of the pre-polymer could easily be increased from 5000 to 12000 by extending the reaction time. The pre-polymer PBM was successfully cross-linked with UV-radiation to form a clear, transparent, colorless, flexible, and strong film. PBM as a macroinitiator for L-lactide (LLA) and epsilon-caprolactone (CL) polymerizations highly increased the ductility of the LLA-polymer, while maintaining the strength, compared to PLLA polymerized with common initiators. The tensile properties of PCL were also improved. The linear PCL-PBM and PLLA-PBM polymers were easily cross-linked to give polymers with greater strength and higher modulus as the result.

Place, publisher, year, edition, pages
2010. Vol. 22, no 9, 3009-3014 p.
Keyword [en]
epsilon-caprolactone, cross-linking, enzymatic polymerization, poly(propylene fumarate), l-lactide, 1, 5-dioxepan-2-one, polymers, initiator, kinetics
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-19409DOI: 10.1021/cm100520jISI: 000277194600042Scopus ID: 2-s2.0-77951964678OAI: oai:DiVA.org:kth-19409DiVA: diva2:337456
Funder
Swedish Research Council, 2008-5538
Note
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Macromolecular synthesis of functional degradable aliphatic polyesters and porous scaffold design
Open this publication in new window or tab >>Macromolecular synthesis of functional degradable aliphatic polyesters and porous scaffold design
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

There is an increasing demand for new materials in biomedical applications with material properties that are highly specific for each application area. The search for new materials requires the creation of materials with suitable mechanical properties, functionalities, three-dimensional structures and a controlled degradation profile. The focus of the work described in this thesis has been on the synthesis of functional degradable aliphatic polyesters, on the design of porous scaffolds and on their synthesis with bio-safe catalyst/initiator systems.  

An unsaturated aliphatic polyester has been synthesized by condensation polymerization to produce poly(but-2-ene-1,4-diyl malonate) (PBM), which was applicable as a cross-linked network and as a macro-co-initiator for the ring-opening polymerization (ROP) of cyclic ester monomers. The method of preparation of PBM was simple and straightforward and there was no need to purify the monomers or add a catalyst. PBM was successfully cross-linked with UV-radiation to form a transparent, colorless, flexible and strong film. When PBM was used as a macro-co-initiator, a triblock copolymer was formed with PBM middle blocks and poly(L-lactide) (PLLA) or poly(ε-caprolactone) side blocks. The ductility of the triblock copolymer of PLLA was greatly enhanced and the strength was maintained compared to the polymer obtained when PLLA was polymerized with ethylene glycol as co-initiator. The triblock copolymers were easily cross-linked to give materials with greater strength and higher modulus as a result. When these polymers were subjected to hydrolysis, a rapid initial hydrolysis of the amorphous PBM middle block changed the microstructure from triblock to diblock, with a significant reduction in ductility and number average molecular weight. Highly porous scaffolds were created from these functional materials and the mechanical properties were evaluated by a cyclic compression test under mimicked physiological conditions.

Copolymers of L-lactide (LLA) and ε-caprolactone (CL), trimethylene carbonate (TMC) or 1,5-dioxepane-2-one (DXO) have been synthesized with a low stannous-2-ethyl hexanoate  (Sn(Oct)2) ratio and used to fabricate porous tubular scaffolds. The tubes were designed to have a range of mechanical properties suitable for nerve regeneration, with different porosities and different numbers of layers in the tube wall. The adaptability of an immersion-coating and porogen-leaching technique was demonstrated by creating tubes with different dimensions.

Although a low amount of residual tin (monomer-to-initiator ratio of 10000:1) is accepted in biomedical applications, an efficient bio-safe catalyst/initiator system would be favored. The catalytic activities of bio-safe Bi (III) acetate and creatinine towards the ROP of LLA have been compared with those of Sn(Oct)2-based systems and with those of a system catalyzed by enzymes. All these systems were shown to be suitable catalysts for the synthesis of high and moderate molecular weight PLLAs.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 75 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:45
Keyword
functional polyesters, condensation polymerization, L-lactide, ε-caprolactone, triblock copolymer, mechanical properties, porous scaffolds, tissue engineering, ring-opening polymerization, Bi(III) acetate, creatinine, stannous 2-ethylhexanoate, enzyme, degradation products
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-38583 (URN)978-91-7501-060-1 (ISBN)
Public defence
2011-09-22, F3, Lindstedtsvägen 26, KTH, Stockholm, 13:00 (English)
Opponent
Supervisors
Note
QC 20110901Available from: 2011-08-30 Created: 2011-08-29 Last updated: 2011-09-01Bibliographically approved

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