Poly(1,3-Butylene Fumerate) and Poly(1,3-Butylene Fumerate)-co-(1,3-Butylene Maleate) as Electrospun Scaffold Materials
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1239-VV05-02
Poly(1,3-Butylene Fumerate) and Poly(1,3-Butylene Fumerate)-co-(1,3-Butylene Maleate) as Electrospun Scaffold Materials Kirsten N. Cicotte1,2, Shawn M. Dirk1, Elizabeth L. Hedberg-Dirk,2 1
Organic Materials Department, Sandia National Laboratories, P.O. Box 5800, Albuquerque, NM 87185, USA. 2 Center for Biomedical Engineering and Department of Chemical and Nuclear Engineering, University of New Mexico, Albuquerque, NM 87131, USA.
ABSTRACT Poly(butylene fumerate) (PBF) and poly(butylene fumerate)-co-(butylene maleate) (PBFcBM) have been synthesized from the ring opening and condensation reactions of maleic anhydride (MA) and 1,3-butanediol (BD). PBFcBM synthesized in this way contains greater than 85% maleate groups. Both PBF and PBFcBM have a glass transition temperature (Tg) below room temperature and therefore cannot be electrospun using the conventional electrospinning process as a non-porous film results. To facilitate production of nonwoven micro- and nano-fiber mats, a UV-source (λ=356 nm) was used in combination with a photoinitator loaded polymer solution to initiate the crosslinking reaction of the fumerate and maleate functional groups as the fibers were produced. The resulting non-woven fiber mats are potentially suitable scaffolds for tissue engineering and drug delivery application. INTRODUCTION Poly(propylene fumerate) has previously been synthesized for the fabrication of biodegradable scaffolds for bone tissue engineering. Traditionally, this polymer has been synthesized through either a fumaryl chloride route1 or an ethyl fumerate route2. However, PPF fabricated in the aforementioned way degrades slowly.3 We have previously explored the use of maleic anhydride and 1,2-propanediol to form a co-polymer of poly(propylene fumerate)-co(propylene maleate) (PPFcPM). PPFcPM has a glass transition (Tg) below room temperature and can be crosslinked through its unsaturated double bonds using an free radical initiator system4. Previous reports have explored the polycondensation reaction of maleic anhydride, focusing on the fumerate to maleate isomerization with the use of different linear glycols3, 5-7. Herein, we explore the substitution of 1,3-butane diol (BD) for 1,2-propanediol (PD) in the polycondensation reaction. For use in vivo, a material must be biodegradable, with its degradation products easily broken down and expelled from the body. BD, and therefore our polymers, should be metabolized primarily in the liver due to its high concentrations of the enzymes alcohol dehydrogenase and aldehyde dehydrogenase.9 This proceeding explores the step growth polycondensation of unsaturated polyesters of PBF and PBFcBM as well as the fabrication of highly porous fibrous scaffolds that have potential use in tissue engineering and drug delivery.
EXPERIMENTAL Poly(1,3-Butylene Fumerate) Synthesis Maleic anhydride (MA) (Aldrich, briquettes 99%) (10 g, 102 mmol), 1,3-butanediol (BD) (Aldrich, Reagent Plus®, 99% )(9.2 g, 102 mmol) and p-toluensulfonic acid (TsOH) (Acros Organics) (0.2 g, 1.02 mmol) wer
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