The catalyst-free polytransesterification for obtaining linear PGS optimized with use of 22 factorial design

• Autorzy: Wrzecionek Michał , Howis Joanna , Marek Paulina H. , Ruśkowski Paweł , Gadomska-Gajadhur Agnieszka

Identyfikatory

DOI

10.24425/cpe.2021.137338

• Języki publikacji: EN

Abstrakty

EN

Poly(glycerol sebacate) (PGS) is a polyester that is particularly useful for tissue engineering appli- cations. Many researchers have focused on the application and characterization of materials made from PGS. Synthesis is often superficially described, and the prepolymer is not characterized before crosslinking. Considering the different functionality of each monomer (glycerine – 3, sebacic acid – 2), materials with a branched structure can be obtained before the crosslinking process. Branched struc- tures are not desirable for elastomers. In this work, method to obtain linear PGS resins is presented. Moreover, synthesis was optimized with the use of the Design of Experiments method for minimizing the degree of branching and maximizing the molecular weight. The process was described via mathe- matical models, which allows to the association of process parameters with product properties. In this work ca. 1kDa and less than 10% branched PGS resin was produced. This resin could be used to make very flexible elastomers because branching is minimized.

Słowa kluczowe

EN

poly(glycerol sebacate); polycondensation; optimization

PL

poli(sebacynian glicerolu); polikondensacja; optymalizacja

• Wydawca: Komitet Inżynierii Chemicznej i Procesowej Polskiej Akademii Nauk
• Czasopismo: Chemical and Process Engineering
• Rocznik: 2021
• Tom: Vol. 42, nr 1
• Strony: 43--–52
• Opis fizyczny: Bibliogr. 31 poz., rys., tab.

Twórcy

autor

Wrzecionek Michał

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland

autor

Howis Joanna

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland

autor

Marek Paulina H.

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland
• University of Warsaw, Faculty of Chemistry, Pasteura 1, 02-093 Warsaw, Poland

autor

Ruśkowski Paweł

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland

autor

Gadomska-Gajadhur Agnieszka

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warsaw, Poland

Bibliografia

• 1. Denis P., Wrzecionek M., Gadomska-Gajadhur A., Sajkiewicz P., 2019. Poly(glycerol sebacate)–poly(l-lactide) nonwovens towards attractive electrospun material for tissue engineering. Polymers, 11, 2113. DOI: 10.3390/polym11122113.
• 2. Fernandes B.S., Carlos Pinto J., Cabral-Albuquerque E.C.M., Fialho R.L., 2015. Free-radical polymerization of urea, acrylic acid, and glycerol in aqueous solutions. Polym. Eng. Sci., 55, 1219–1229. DOI: 10.1002/pen.24081.
• 3. Gadomska-Gajadhur A.,Wrzecionek M., Matyszczak G., Pi˛etowski P.,Wi˛ecław M., Ruśkowski P., 2018. Optimization of poly(glycerol sebacate) synthesis for biomedical purposes with the design of experiments. Org. Process Res. Dev., 22, 1793–1800. DOI: 10.1021/acs.oprd.8b00306.
• 4. Gao J., Crapo P.M., Wang Y., 2006. Macroporous elastomeric scaffolds with extensive micropores for soft tissue engineering. Tissue Eng., 12, 917–925. DOI: 10.1089/ten.2006.12.917.
• 5. Godinho B., Gama N., Barros-Timmons A., Ferreira A., 2018. Enzymatic synthesis of poly(glycerol sebacate) prepolymer with crude glycerol, by-product from biodiesel prodution. AIP Conference Proceedings, 1981, 020031. DOI: 10.1063/1.5045893.
• 6. Harris J.J., Lu S., Gabriele P., 2018. Commercial challenges in developing biomaterials for medical device development. Polym. Int., 67, 969–974. DOI: 10.1002/pi.5590.
• 7. Higuchi T., Kinoshita A., Takahashi K., Oda S., Ishikawa I., 1999. Bone regeneration by recombinant human bone morphogenetic protein-2 in rat mandibular defects. An experimental model of defect filling. J. Periodontology, 70, 1026–1031. DOI: 10.1902/jop.1999.70.9.1026.
• 8. Kafouris D., Kossivas F., Constantinides C., Nguyen N.Q.,Wesdemiotis C., Patrickios C.S., 2013. Biosourced amphiphilic degradable elastomers of poly(glycerol sebacate): synthesis and network and oligomer characterization. Macromolecules, 46, 622–630. DOI: 10.1021/ma3016882.
• 9. Kemppainen J.M., Hollister S.J., 2010. Tailoring the mechanical properties of 3D-designed poly(glycerol sebacate) scaffolds for cartilage applications. J. Biomed. Mater. Res. Part A, 94A, 9–18. DOI: 10.1002/jbm.a.32653.
• 10. Kharaziha M., Nikkhah M., Shin S.-R., Annabi N., Masoumi N., Gaharwar A.K., Camci-Unal G., Khademhosseini A., 2013. PGS:Gelatin nanofibrous scaffolds with tunable mechanical and structural properties for engineering cardiac tissues. Biomaterials, 34, 6355–6366. DOI: 10.1016/J.BIOMATERIALS.2013.04.045.
• 11. Kokubo S., Fujimoto R., Yokota S., Fukushima S., Nozaki K., Takahashi K., Miyata K., 2003. Bone regeneration by recombinant human bone morphogenetic protein-2 and a novel biodegradable carrier in a rabbit ulnar defect model. Biomaterials, 24, 1643–1651. DOI: 10.1016/S0142-9612(02)00551-3.
• 12. Kumar A., Khan A., Malhotra S., Mosurkal R., Dhawan A., Pandey M.K., Singh B.K., Kumar R., Prasad A.K.,
• 13. Sharma S.K., Samuelson L.A., Cholli A.L., Len C., Richards N.G.J., Kumar J., Haag R.,Watterson A.C., Parmar V.S., 2016. Synthesis of macromolecular systems via lipase catalyzed biocatalytic reactions: applications and future perspectives. Chem. Soc. Rev., 45, 6855–6887. DOI: 10.1039/C6CS00147E.
• 14. Landim L.B., Pinto J.C., Cabral-Albuquerque E.C.M., Cunha S., Fialho R.L., 2018. Synthesis and characterization of copolymers of urea-succinic acid-ethylene glycol and copolymers of urea-succinic acid-glycerol. Polym. Eng. Sci. 58, 1575–1582. DOI: 10.1002/pen.24746.
• 15. Larsson A., Israelsson M., Lind F., Seemann M., Thunman H., 2014. Using ilmenite to reduce the tar yield in a dual fluidized bed gasification system. Energy Fuels, 28, 2632–2644. DOI: 10.1021/ef500132p.
• 16. Li C.J., Trost B.M., 2008. Green chemistry for chemical synthesis. PNAS, 105, 13197–13202. DOI: 10.1073/pnas.0804348105.
• 17. Li Y., Cook W.D., Moorhoff C., Huang W.-C., Chen Q.-Z., 2013. Synthesis, characterization and properties of biocompatible poly(glycerol sebacate) pre-polymer and gel. Polym. Int., 62, 534–47. DOI: 10.1002/pi.4419.
• 18. Liu G., Hinch B., Beavis A.D., 1996. Mechanisms for the transport of alpha,omega-dicarboxylates through the mitochondrial inner membrane. J. Biol. Chem., 271, 25338–25344. DOI: 10.1074/jbc.271.41.25338.
• 19. Liu L.L., Yi F.C., Cai W., 2012. Synthesis and shape memory effect of poly(glycerol-sebacate) elastomer. Adv. Mater. Res., 476–478, 2141–2144. DOI: 10.4028/www.scientific.net/AMR.476-478.2141.
• 20. Liu Q., Tian M., Ding T., Shi R., Feng Y., Zhang L., Chen D., Tian W., 2007. Preparation and characterization of a thermoplastic poly(glycerol sebacate) elastomer by two-step method. J. Appl. Polym. Sci., 103, 1412–19. DOI: 10.1002/app.24394.
• 21. Loh X.J., Abdul Karim A., Owh C., 2015, Poly(glycerol sebacate) biomaterial: synthesis and biomedical applications. J. Mater. Chem. B, 3, 7641–7652. DOI: 10.1039/c5tb01048a.
• 22. Martina M., Hutmacher D.W., 2007. Biodegradable polymers applied in tissue engineering research: a review. Polym. Int., 56, 145–157. DOI: 10.1002/pi.2108.
• 23. Otera J., 1993. Transesterification. Chem. Rev., 93, 1449–1470. DOI: 10.1021/cr00020a004. Rai R., Tallawi M., Grigore A., Boccaccini A.R., 2012. Synthesis, properties and biomedical applications of poly(glycerol sebacate) (PGS): A review. Prog. Polym. Sci., 37, 1051–1078. DOI: 10.1016/j.progpolymsci.2012.02.001.
• 24. Ravichandran R., Venugopal J.R., Sundarrajan S., Mukherjee S., Ramakrishna S., 2011. Poly(glycerol seba-cate)/gelatin core/shell fibrous structure for regeneration of myocardial infarction. Tissue Eng. Part A, 17, 1363–1373. DOI: 10.1089/ten.tea.2010.0441.
• 25. Ravichandran R., Venugopal J.R., Sundarrajan S., Mukherjee S., Sridhar R., Ramakrishna S., 2012. Minimally invasive injectable short nanofibers of poly(glycerol sebacate) for cardiac tissue engineering. Nanotechnology, 23, 385102. DOI: 10.1088/0957-4484/23/38/385102.
• 26. Sant S.,Hwang C.M., Lee S.-H., Khademhosseini A., 2011. Hybrid PGS-PCL microfibrous scaffolds with improved mechanical and biological properties. J. Tissue Eng. Regener. Med., 5, 283–291. DOI: 10.1002/term.313.
• 27. Saudi A., Rafienia M., Zargar Kharazi A., Salehi H., Zarrabi A., Karevan M., 2019. Design and fabrication of poly (glycerol sebacate)-based fibers for neural tissue engineering: synthesis, electrospinning, and characterization. Polym. Adv. Technol., 30, 1427–1440. DOI: 10.1002/pat.4575.
• 28. Slavko E., Taylor M.S., 2017. Catalyst-controlled polycondensation of glycerol with diacyl chlorides: linear polyesters from a trifunctional monomer. Chem. Sci., 8, 7106–7111. DOI: 10.1039/C7SC01886J.
• 29. Wang Y., Ameer G.A., Sheppard B.J., Langer R., 2002. A tough biodegradable elastomer. Nat. Biotechnol., 20, 602–606. DOI: 10.1038/nbt0602-602.
• 30. Wrzecionek M., Ruśkowski P., Gadomska-Gajadhur A., Gadomska-Gajadhur A., 2021. Mathematically described preparation process of poly(glycerol succinate) resins and elastomers—meeting science with industry. Polym. Adv.Technol., 32, 2042–2051. DOI: 10.1002/pat.5233.
• 31. Xu B., Cook W.D., Zhu C., Chen Q., 2016. Aligned core/shell electrospinning of poly(glycerol sebacate)/poly(l-lactic acid) with tuneable structural and mechanical properties. Polym. Int., 65, 423–429. DOI: 10.1002/pi.5071.

Uwagi

Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).