Biobased long-chain aliphatic polyesters of 1,12-dodecanedioic acid with a variety of diols: Odd-even effect and mechanical properties

Materials Today Communications - Tập 19 - Trang 450-458 - 2019
Changfeng Zhou1, Zhiyong Wei1, Yang Yu1, Shengnan Shao1, Xuefei Leng1, Yanshai Wang1, Yang Li1
1State Key Laboratory of Fine Chemicals, Liaoning Key Laboratory of Polymer Science and Engineering, Department of Polymer Science and Engineering, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China

Tài liệu tham khảo

Gandini, 2015, From monomers to polymers from renewable resources: recent advances, Prog. Polym. Sci., 48, 1, 10.1016/j.progpolymsci.2014.11.002 Tsui, 2013, Biodegradable polyesters from renewable resources, Annu. Rev. Chem. Biomol. Eng., 4, 143, 10.1146/annurev-chembioeng-061312-103323 Zhu, 2016, Sustainable polymers from renewable resources, Nature, 540, 354, 10.1038/nature21001 Díaz, 2014, Synthesis, properties and applications of biodegradable polymers derived from diols and dicarboxylic acids: from polyesters to poly(ester amide)s, Int. J. Mol. Sci., 15, 7064, 10.3390/ijms15057064 Tachibana, 2018, Synthesis, physical properties, and biodegradability of biobased poly(butylene succinate-co-butylene oxabicyclate), ACS Sustain. Chem. Eng., 6, 10806, 10.1021/acssuschemeng.8b02112 Tan, 2017, Bio-based poly(butylene succinate-co-hexamethylene succinate) copolyesters with tunable thermal and mechanical properties, Eur. Polym. J., 86, 162, 10.1016/j.eurpolymj.2016.11.017 Castro-Aguirre, 2016, Poly(lactic acid)-mass production, processing, industrial applications, and end of life, Adv. Drug Deliv. Rev., 107, 333, 10.1016/j.addr.2016.03.010 Zia, 2016, Recent developments and future prospects on bio-based polyesters derived from renewable resources: a review, Int. J. Biol. Macromol., 82, 1028, 10.1016/j.ijbiomac.2015.10.040 Manavitehrani, 2016, Biomedical applications of biodegradable polyesters, Polymers, 8, 20, 10.3390/polym8010020 Tian, 2012, Biodegradable synthetic polymers: preparation, functionalization and biomedical application, Prog. Polym. Sci., 37, 237, 10.1016/j.progpolymsci.2011.06.004 Wanamaker, 2007, Renewable-resource thermoplastic elastomers based on polylactide and polymenthide, Biomacromolecules, 11, 3634, 10.1021/bm700699g Pepels, 2015, Influence of the main-chain configuration on the mechanical properties of linear aliphatic polyesters, Macromolecules, 48, 5845, 10.1021/acs.macromol.5b01089 Sorrentino, 2018, Polyethylene-like macrolactone-based polyesters: rheological, thermal and barrier properties, Mater. Today Commun., 17, 380, 10.1016/j.mtcomm.2018.10.001 Stempfle, 2016, Long-chain aliphatic polymers to bridge the gap between semicrystalline polyolefins and traditional polycondensates, Chem. Rev., 116, 4597, 10.1021/acs.chemrev.5b00705 Ortmann, 2013, Long-spaced aliphatic polyesters, Macromolecules, 46, 7213, 10.1021/ma401305u Stempfle, 2013, Which polyesters can mimic polyethylene?, Macromol. Rapid Commun., 34, 47, 10.1002/marc.201200611 Liu, 2011, Polymers from fatty acids: poly(ω-hydroxyl tetradecanoic acid) synthesis and physico-mechanical studies, Biomacromolecules, 12, 3291, 10.1021/bm2007554 Wang, 2018, Ring-opening polymerization with Lewis pairs and subsequent nucleophilic substitution: a promising strategy to well-defined polyethylene-like polyesters without transesterification, Macromolecules, 51, 836, 10.1021/acs.macromol.7b02378 Hodge, 2014, Entropically driven ring-opening polymerization of strainless organic macrocycles, Chem. Rev., 114, 2278, 10.1021/cr400222p Jose, 2014, Thermoplastic polyesters and co-polyesters derived from vegetable oil: synthesis and optimization of melt polycondensation for medium and long chain poly(ω-hydroxyfatty acid)s and their ester derivatives, Polym. Chem., 5, 3203, 10.1039/C3PY01261A Genovese, 2014, Biodegradable long chain aliphatic polyesters containing ether-linkages: synthesis, solid-state, and barrier properties, Ind. Eng. Chem. Res., 53, 10965, 10.1021/ie5017865 Ayorinde, 1989, Synthesis of dodecanedioic acid fromvernonia galamensis oil, J. Am. Oil Chem. Soc., 66, 690, 10.1007/BF02669953 Cao, 2017, High-level productivity of α,ω-dodecanedioic acid with a newly isolated Candida viswanathii strain, J. Ind. Microbiol. Biotechnol., 44, 1191, 10.1007/s10295-017-1948-6 Barbiroli, 2003, Polyethylene like polymers. Aliphatic polyesters of dodecanedioic acid: 1. Synthesis and properties, Eur. Polym. J., 39, 655, 10.1016/S0014-3057(02)00280-X Celli, 2007, Thermal properties of poly(alkylene dicarboxylate)s derived from 1,12-dodecanedioic acid and even aliphatic diols, J. Polym. Sci. Part B: Polym. Phys., 45, 1053, 10.1002/polb.21174 Lu, 2017, High molecular weight polyesters derived from biobased 1, 5-pentanediol and a variety of aliphatic diacids: synthesis, characterization, and thermo-mechanical properties, ACS Sustain. Chem. Eng., 5, 6159, 10.1021/acssuschemeng.7b01050 Yu, 2017, Miscibility and competition of cocrystallization behavior of poly(hexamethylene dicarboxylate)s aliphatic copolyesters: effect of chain length of aliphatic diacids, Eur. Polym. J., 92, 71, 10.1016/j.eurpolymj.2017.04.036 Berti, 2008, Novel copolyesters based on poly(alkylene dicarboxylate)s: 1. Thermal behavior and biodegradation of aliphatic-aromatic random copolymers, Eur. Polym. J., 44, 3650, 10.1016/j.eurpolymj.2008.08.039 Berti, 2009, Novel copolyesters based on poly(alkylene dicarboxylate)s: 2. Thermal behavior and biodegradation of fully aliphatic random copolymers containing 1,4-cyclohexylene rings, Eur. Polym. J., 45, 2402, 10.1016/j.eurpolymj.2009.04.034 Jia, 2018, Fully bio-based polyesters derived from 2,5-furandicarboxylic acid (2,5-FDCA) and dodecanedioic acid (DDCA): from semicrystalline thermoplastic to amorphous elastomer, J. Appl. Polym. Sci., 135, 46076, 10.1002/app.46076 Chen, 2017, Synthesis of copolyesters with bio-based lauric diacid: structure and physico-mechanical studies, RSC Adv., 7, 55418, 10.1039/C7RA11771J Papageorgiou, 2010, Synthesis and comparative study of biodegradable poly(alkylene sebacate)s, J. Polym. Sci. Part B: Polym. Phys., 48, 672, 10.1002/polb.21937 Kong, 2014, Synthesis and characterization of high-molecular weight aliphatic polyesters from monomers derived from renewable resources, J. Appl. Polym. Sci., 131, 40579, 10.1002/app.40579 Yashiro, 2009, Syntheses of polyesters from succinic anhydride and various diols catalyzed by metal triflates, Macromol. Chem. Phys., 210, 1607, 10.1002/macp.200900189 Garcia, 2014, Polyoxalates from biorenewable diols via oxalate metathesis polymerization, Polym. Chem., 5, 955, 10.1039/C3PY01185B Berti, 2007, The effect of aliphatic chain length on thermal properties of poly(alkylene dicarboxylate)s, e-Polymers, 10.1515/epoly.2007.7.1.658 Bikiaris, 2008, Correlation between chemical and solid-state structures and enzymatic hydrolysis in novel biodegradable polyesters. The case of poly(propylene alkanedicarboxylate)s, Macromol. Biosci., 8, 728, 10.1002/mabi.200800035 Cai, 2011, Real-time structure changes during uniaxial stretching of poly(ω-pentadecalactone) by in situ synchrotron WAXD/SAXS techniques, Macromolecules, 44, 3874, 10.1021/ma102949h Stempfle, 2011, Long-chain linear C19 and C23 monomers and polycondensates from unsaturated fatty acid esters, Macromolecules, 44, 4159, 10.1021/ma200627e Pepels, 2013, From polyethylene to polyester: influence of ester groups on the physical properties, Macromolecules, 46, 7668, 10.1021/ma401403x Almontassir, 2004, Molecular packing of polyesters derived from 1,4-butanediol and even aliphatic dicarboxylic acids, Macromolecules, 37, 5300, 10.1021/ma049939l Jourdan, 1995, Structural study of linear polyesters. 1. Crystal structure of poly(trimethylene sebacate), established from X-ray and electron diffraction data, Macromolecules, 28, 8086, 10.1021/ma00128a017 Pepels, 2015, Mimicking (linear) low-density polyethylenes using modified polymacrolactones, Macromolecules, 48, 4779, 10.1021/acs.macromol.5b00820