Hydroxyl functionalized renewable polyesters derived from 10-undecenoic acid: Polymer structure and post-polymerization modification

Gandini, 2016, The progress of polymers from renewable resources: furans, vegetable oils and polysaccharides, Chem. Rev., 116, 1637, 10.1021/acs.chemrev.5b00264 Gandini, 2015, From monomers to polymers from renewable resources: recent advances, Prog. Polym. Sci., 48, 1, 10.1016/j.progpolymsci.2014.11.002 Gallezot, 2011, Direct routes from biomass to end-products, Catal. Today, 167, 31, 10.1016/j.cattod.2010.11.054 Sheldon, 2014, Green and sustainable manufacture of chemicals from biomass: state of the art, Green Chem., 16, 950, 10.1039/C3GC41935E Lligadas, 2010, Plant oils as platform chemicals for polyurethane synthesis: current state-of-the-art, Biomacromolecules, 11, 2825, 10.1021/bm100839x Van Steen, 2009, Undecylenic acid: a valuable and physiologically active renewable building block from castor oil, ChemSusChem, 2, 692, 10.1002/cssc.200900075 Bigot, 2016, Undecylenic acid: a tunable bio-based synthon for materials applications, Eur. Polym. J., 74, 26, 10.1016/j.eurpolymj.2015.11.008 Seyednejad, 2011, Functional aliphatic polyesters for biomedical and pharmaceutical applications, J. Control. Rel., 152, 168, 10.1016/j.jconrel.2010.12.016 Oh, 2011, Polylactide (PLA)-based amphiphilic block copolymers: synthesis, self-assembly, and biomedical applications, Soft Matter., 7, 5096, 10.1039/c0sm01539c Vilela, 2014, The quest for sustainable polyesters – insights into the future, Polym. Chem., 5, 3119, 10.1039/C3PY01213A Hillmyer, 2014, Aliphatic polyester block polymers: renewable, degradable, and sustainable, Acc. Chem. Res., 47, 2390, 10.1021/ar500121d Kunduru, 2015, Castor oil based biodegradable polyesters, Biomacromolecules, 16, 2572, 10.1021/acs.biomac.5b00923 Manavitehrani, 2016, Biomedical applications of biodegradable polyesters, Polymers, 8, 1, 10.3390/polym8010020 Vert, 2005, Aliphatic polyesters: great degradable polymers that cannot do everything, Biomacromolecules, 6, 538, 10.1021/bm0494702 Williams, 2007, Synthesis of functionalized biodegradable polyesters, Chem. Soc. Rev., 36, 1573, 10.1039/b614342n Tong, 2017, New chemistry in funcional aliphatic polyesters, Ind. Eng. Chem. Res., 56, 4207, 10.1021/acs.iecr.7b00524 Gerhardt, 2006, Functional lactide monomers: methodology and polymerization, Biomacromolecules, 7, 1735, 10.1021/bm060024j Leemhuis, 2006, Functionalized Poly(α-hydroxy acid)s via ring-opening polymerization: toward hydrophilic polyesters with pendant hydroxyl groups, Macromolecules, 39, 3500, 10.1021/ma052128c El Habnouni, 2009, Synthesis and ring opening polymerization of a new functional lactone, α-Iodo-ε-caprolactone: a novel route to functionalized aliphatic polyesters, Macromol. Rapid Commun., 30, 165, 10.1002/marc.200800596 Hahn, 2013, OH-functional polyesters based on malic acid: influence of the OH-groups onto the thermal properties, E. Polym. J., 49, 217, 10.1016/j.eurpolymj.2012.09.020 Fuoco, 2016, Route to aliphatic poly(ester)s with thiol pendant groups: from monomer design to editable porous scaffolds, Biomacromolecules, 17, 1383, 10.1021/acs.biomac.6b00005 Slavko, 2017, Catalyst-controlled polycondensation of glicerol with diacyl chlorides: linear polyesters from a trifunctional monomer, Chem. Sci., 8, 7106, 10.1039/C7SC01886J Zhang, 2003, Synthesis and characterization of poly(butylene succinate-co-butylene malate): a new biodegradable copolyester bearing hydroxyl pendant groups, Biomacromolecules, 4, 437, 10.1021/bm0201183 Hao, 2005, New facile approach to novel water-soluble aliphatic poly(butylene tartarate)s bearing reactive hydroxyl pendant groups, Biomacromolecules, 6, 3474, 10.1021/bm050317x You, 2010, A functionable polyester with free hydroxyl groups and tunable physiochemical and biological properties, Biomaterials, 31, 3129, 10.1016/j.biomaterials.2010.01.023 Y. Yan, D. Siegwart, J. Scalable synthesis and derivation of functional polyesters bearing ene and epoxide side chains, Polym. Chem. 5 (2014) 1362–1371. Kalelkar, 2016, Synthesis of an alkene-containing copolylactide and its facile modification by the addition of thiols, Macromolecules, 49, 2609, 10.1021/acs.macromol.5b02431 Beyazkilic, 2014, Vinylsulfide-containing polyesters and copolyesters from fatty acids: Thiol-yne monomer synthesis and thiol-ene functionalization, Macromol. Chem. Phys., 215, 2248, 10.1002/macp.201400191 M. Moreno, G. Lligadas, J. C. Ronda, M. Galià, V. Cádiz, Polyketoesters from oleic acid. Synthesis and functionalization, Green. Chem. 4 (2014) 1847–1853. Beyazkilic, 2015, Synthesis and functionalization of vinylsulfide and ketone-containing aliphatic copolyesters from fatty acids, Polymer, 79, 290, 10.1016/j.polymer.2015.10.024 C. Lluch, M. Calle, G. Lligadas J. C. Ronda M. Galià, V. Cádiz, Versatile post-polymerization modifications of a functional polyester from castor oil, Eur. Polym. J. 72 (2015) 64–71. Noga, 2008, Synthesis and modification of functional poly(lactide) copolymers: toward biofunctional materials, Biomacromolecules, 9, 2056, 10.1021/bm800292z White, 2007, Step-growth polymerization of 10,11-epoxyundecanoic acid. Synthesis and properties of a new hydroxy-functionalized thermoplastic polyester, Polymer, 48, 3990, 10.1016/j.polymer.2007.05.031 Miao, 2008, Chemoenzymatic synthesis of oleic acid-based polyesters for use as highly stable biomaterials, J. Polym. Sci. Part A: Polym. Chem., 46, 4243, 10.1002/pola.22721 De Smet, 2014, MacroRAFT agents from renewable resources and their use as polymeric scaffolds in a grafting from approach, Polym. Chem, 5, 3163, 10.1039/C3PY01288C Harris, 1935, Addition of hydrogen bromide to triple and to double bonds. Undecynoic, undecenoic, and 10,11-epoxyundecoic acids, J. Chem. Soc., 1572, 10.1039/jr9350001572 Bories-Azeau, 2004, Synthesis of near-monodisperse acidic homopolymers and block copolímers from hydroxylated methacrylic copolímers using succínic anhydride under mild conditions, Macromolecules, 37, 8903, 10.1021/ma048726t S. Warwel, M. R. gen Klaas, Chemo-enzymatic epoxydation of unsaturated carboxylic acid, J. Mol. Cat. B: Enzym. 1 (1995) 29–35. Aouf, 2014, The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds, Green Chem., 16, 1740, 10.1039/C3GC42143K Alvey, 1969, Investigation of the epoxide-carboxylic acid reaction in model compound and polymerization reactions, J. Polym. Sci. Part A: Polym. Chem., 7, 2117, 10.1002/pol.1969.150070809 Blank, 2002, Catalysis of epoxy-carboxyl reaction, J. Coat. Technol., 74, 33, 10.1007/BF02720158 You, 2012, A versatile synthetic platform for a wide range of functionalized biomaterials, Adv. Funct. Mater., 22, 2812, 10.1002/adfm.201102024 Kim, 2013, Efficient ring opening reaction of epoxides with oxygen nucleophyles catalyzed by quaternary onium salt, Bull. Kor. Chem. Soc., 34, 2286, 10.5012/bkcs.2013.34.8.2286 Pratt, 2006, Triazabicyclodecene: a simple bifunctional organocatalyst for acyl transfer and ring-opening polymerization of cyclic esters, J. Am. Chem. Soc., 128, 4556, 10.1021/ja060662+ Tang, 2011, Metal-free synthesis of novel biobased dihydroxy-terminated aliphatic polyesters as building blocks for thermoplastic polyurethanes, J. Polym. Sci. Part A: Polym. Chem., 49, 2959, 10.1002/pola.24732 Gross, 2001, Polymer synthesis by in vitro enzyme catalysis, Chem. Rev., 101, 3793, 10.1021/cr0002590 Matsumura, 2006, Enzymatic synthesis of polyesters via ring-opening polymerization, Adv. Polym. Sci., 194, 95, 10.1007/12_030 Kobayashi, 2010, Lipase-catalyzed polyester synthesis – a green polymer chemistry, Proc. Jpn. Acad. Ser., 86, 338, 10.2183/pjab.86.338 De Vries, 2003, Biocatalytic conversion of epoxides, Curr. Opin. Biotechnol., 14, 414, 10.1016/S0958-1669(03)00102-2 Soeda, 2002, Enzymatic ring-opening polymerization of oxiranes and dicarboxylic anhydrides, Macromol. Biosci., 2, 429, 10.1002/mabi.200290003 Douka, 2017, A review of enzymatic polymerization to produce polycondensation polymers: the case of aliphatic polyesters, polyamides and polyesteramides, Prog. Polym. Sci. Elenkov, 2007, Enzyme-catalyzed nucleophilic ring opening of epoxides for the preparation of enantiopure tertiary alcohols, Adv. Synth. Catal., 349, 2279, 10.1002/adsc.200700146 C. Valverde, G. Lligadas, J.C. Ronda, M. Galià, V. Cádiz. Hydrolytic and enzymatic degradation studies on aliphatic 10-undecenoic acid-based polyesters. Polym Degrad. Stab. (2018) (submited for publication). Warwel, 2000, Ring-opening of oleochemical epoxides catalyzed by aluminoxane/acetylacetone, Eur. Polym. J., 36, 2655, 10.1016/S0014-3057(00)00046-X Testud, 2017, Hyperbranched polyesters by polycondensation of fatty acid-based ABn-type monomers, Green Chem., 19, 259, 10.1039/C6GC02294D Lligadas, 2006, J. Polym. Sci. Part A: Polym. Chem., 44, 634, 10.1002/pola.21201 Bengtsson, 2010, Molecular weight and thermal properties of polyhydroxyalkanoates produced from fermented sugar molasses by open mixed cultures, J. Biotech., 147, 172, 10.1016/j.jbiotec.2010.03.022 Brioude, 2007, Synthesis and characterization of aliphatic polyesters from glicerol, by-product of biodièsel production, and adipic acid, Mater. Res., 10, 335, 10.1590/S1516-14392007000400003 Newmark, 1971, Nuclear magnetic resonance study of the conformations of valine and phenylalanine derivatives, J. Phys. Chem., 75, 505, 10.1021/j100674a011 Marcovici-Mizrahi, 1996, On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding, J. Org. Chem., 61, 8402, 10.1021/jo961446u Hu, 2012, Rotamers or diastereoisòmers? An overlooked NMR solution, J. Org. Chem., 77, 5198, 10.1021/jo300734r