Abstract
Differences on physicochemical properties of poly(pentadecanolide), PPDL, synthesized by enzymatic ring opening polymerization at two different temperatures, 70 C and 90 C, using Novozyme-430 were assessed. PPDL synthesized at 90°C presents lower molecular weight and crystallinity than the one prepared at 70°C. It was detected by FTIR that PPDL synthesized at 90°C presents a large amorphous phase with more terminal OH groups. A difference in the melting and crystallization behavior was detected by differential scanning calorimetry, DSC, where the melting of the PPDL synthesized at 90°C presents multiple melting and crystallization events at lower temperature than those exhibit by PPDL synthesized at 70°C which presents a well defined single melting and crystallization event. The differences in melting behavior are attributed to the presence of a larger amorphous phase in PPDL synthesized at 90°C due to increased number of terminal OH groups that disrupt the crystalline structure. Thermal stability is also higher in PPDL synthesized at 70°C since the onset of decomposition starts 50°C above that observed in PPDL obtained at 70°C.
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References
A-C Albertsson, RK Srivastava, (2008), Recent developments in enzyme-catalyzed ring-opening polymerization. Adv Drug Delivery Reviews 60, 1077–1093.
P Panlawan, P Luangthongkam, LO Wiemann, V Sieber, E Marie, A Durand, P Inprakhon. (2013) Lipase-catalyzed interfacial polymerization of ω-pentadecalactone in aqueous biphasic medium: A mechanistic study. J Molecular Catal B: Enzym 8869–76.
S Kobayashi. (2009) Recent developments in lipase-catalyzed synthesis of polyesters. Macromol Rapid Commun 30, 237–266.
S Kobayashi, A Makino. (2009) Enzymatic polymer synthesis: An opportunity for green polymer chemistry. Chem Rev 109, 5288=5353.
KS Bisht, LA Henderson, RA Gross, DL Kaplan, G Swift. (1997) Enzyme-catalyzed ring-opening polymerization of ω-pentadecalactone. Macromolecules 30, 2705–2711.
M Gazano, V Malta, ML Focarete, M Scandola, RA Gross. (2003) Crystal structure of poly (ω-pentadecalactone). J Polym Sci: Part B: Polym Phys 41, 1009–1013.
M. De Geus, I. Van der Meulen, B. Goderis, K. Van Hecke, M. Dorschu, H. Van der Werf, C. E. Koning and A Heise., (2010), Performance polymers from renewable monomers:high molecular weight poly(pentadecanolactone) for fiber applications, Polym. Chem., 1, 525–533.
A Kumar, B Karla, A Dekhterman, RA Gross. (2000) Efficient ring-opening polymerization and copolymerization of ε-caprolactone and ω-pentadecalactone catalyzed by Candida antartica Lipase B. Macromolecules 33, 630306309.
S. Nemekawa, H. Uyama, S Kobayasi, (2001) Lipase-catalyzed ring-opening polymerization of lactones in the presence of aliphatic polyesters to ester copolymers, Macromol Chemie Phys, 202, 801–806.
J.R Dyer. (1965) Applications of absorption spectroscopy of organic compounds. Prentice-Hall.
Z Jedlinski, M Juzwa, G Adamus, M Kowalczul, (1996) Anionic polymerization of pentadecanolide. A new route to a potentially biodegradable aliphatic polyester Macromol Chemi & Phys, 197, 2923-2929.
J Xu, B-H Guo, R Yang, Q Wu, G-Q Chen, Z-M Zhang. (2002) In situ FTIR study on melting and crystallization of polyhydroxyalkanoates. Polymer 43, 6893–6899.
A Padermshoke, Y Katsumoto, H Sato, S Ekgasit, I Noda, Y Ozaki. (2005) Melting behavior of poly(3-hydroxybutyrate) investigated by two-dimensional infrared correlation spectroscopy. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 61, 541–550.
H Sato, J Dybal, R Murakami, I Noda, Y Ozaki. (2005) Infrared and Raman spectroscopy and quantum chemistry calculation studies of C-H…O hydrogen bondings and thermal behavior of biodegradable polyhydroxyalkanoate. J Molecular Struc, 744–747, 35-46.
ML Focarete, M Scandola, A Kumar, RA Gross. (2001) Physical characterization of poly ω-pentadecalactone) synthesized by lipase-catalyzed ring-opening polymerization. J Polym Sci: Part B: Polym Phys 39, 1721–1729.
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Herrera-Kao, W., Cervantes-Uc, M., Lara-Ceniceros, T. et al. Characterization of Polyesters Obtained by Enzyme-Catalyzed Ring-Opening Polymerization of Pentadecanolide at high Temperature. MRS Online Proceedings Library 1767, 35–41 (2015). https://doi.org/10.1557/opl.2015.224
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DOI: https://doi.org/10.1557/opl.2015.224