Synthesis of polyglycolic acid copolymers from cationic copolymerization of C1 feedstocks and long chain epoxides

Miller, 2014, Sustainable polymers: replacing polymers derived from fossil fuels, Polym. Chem., 5, 3117, 10.1039/c4py90017k Williams, 2007, Synthesis of functionalized biodegradable polyesters, Chem. Soc. Rev., 35, 1573, 10.1039/b614342n Mayer, 1994, Biodegradable materials: balancing degradability and performance, Trends Polym. Sci., 2, 227 Dobrzynski, 2004, Structure-property relationships of copolymers obtained by ring-opening polymerization of glycolide and ε-caprolactone. Part 1. Synthesis and characterization, Biomacromolecules, 6, 483, 10.1021/bm0494592 Eisenbarth, 2011, Biomaterials Chu, 2005, Sutures Singh, 2010, Structure-processing-property relationship of poly(glycolic acid) for drug delivery systems 1: synthesis and catalysis, Int. J. Polym. Sci., 10.1155/2010/652719 Göktürk, 2017, Biomedical applications of polyglycolic acid (PGA), Sakarya Univ. J. Sci., 21, 1237 Kuredux Polyglycolic Acid (PGA) Resin, A New Polymer Option, http://www.kureha.com/product-groups/pga.htm. Middleton, 1998 Gautier, 2009, Synthesis and rheology of biodegradable poly(glycolic acid) prepared by melt ring-opening polymerization of glycolide, J. Polym. Sci. Part A: Polym. Chem., 47, 1440, 10.1002/pola.23253 E. Gautier, P. Fuertes, P. Cassagnau, J.-P. Pascault, E. Fleury, World forum on advanced polymeric materials synthesis, properties, characterisation, POLYCHAR 18, 2003, p. A-33E. Gautier, P. Fuertes, P. Cassagnau, J.-P. Pascault, E. Fleury, V Argentine-Chilean Polymer Symposium-ARCHIPOL-09, 2009, O.2.B.01-GP, p. 84. Nieuwenhuis, 1992, Synthesis of polylactides, polyglycolides and their copolymers, Clin. Mater., 10, 59, 10.1016/0267-6605(92)90086-9 Maciej, 1999, Application of calcium acetylacetonate to the polymerization of glycolide and copolymerization of glycolide with ε-caprolactone and l-lactide, Macromolecules, 32, 4735, 10.1021/ma981969z Bourisso, 2005, Controlled cationic polymerization of lactide, Macromolecules, 38, 9993, 10.1021/ma051646k https://www.sigmaaldrich.com/catalog/product/sigma/g1796?lang=en&region=TR. Göktürk, 2015, Polyglycolic acid from the direct polymerization of renewable C1 feedstocks, Polym. Chem., 6, 3918, 10.1039/C5PY00230C E. Göktürk, A. G. Pemba, S.A. Miller, Polyglycolic Acid and Copolymers Thereof from C1 Feedstocks, U.S. Patent, 9303118, 2016. Ilg, 2007, Linear low-density polyoxymethylene versus linear low-density polyethylene, Macromolecules, 40, 7739, 10.1021/ma702066y Muro-Small, 2013, A green route to petroleum feedstocks: photochemistry of fats and oils, ACS Sustain. Chem. Eng., 1, 1214, 10.1021/sc400135y Lüftl, 2014 Herzberger, 2016, Polymerization of ethylene oxide, and other alkylene oxides: synthesis, novel polymer architectures, and bioconjugation, Chem. Rev., 116, 2170, 10.1021/acs.chemrev.5b00441 Royals, 1964, α-Pinene oxide reaction with acetic acid- sodium acetate, J. Org. Chem., 29, 2098, 10.1021/jo01030a559 Lal, 2012, Heterogeneous reactions of epoxides in acidic media, J. Phys. Chem. A, 116, 6078, 10.1021/jp2112704 Stekrova, 2014 De Silva, 2003 Carr, 1994, Ring opening of α-pinene epoxide, J. Chem. Soc., Perkin Trans. 2, 1419, 10.1039/P29940001419 Royals, 1966, Reactions of the limonene 1,2-oxides. I. The stereospecific reactions of the (+)-cis- and (+)-trans-limonene 1,2-oxides, J. Org. Chem., 31, 1937, 10.1021/jo01344a062