Abstract
Aliphatic-sulfonated polyesters based on 2,5 FDCA, such as poly(ethylene 2,5-furandicarboxylate)-co-(ethylene sodiosulfonate succinate) or 2,5-PEF-co-PESs were prepared by a melt step-growth polymerization of 2,5-FDCA and Na-DMSS with ethylene glycol. These copolyesters were characterized by 1H-NMR, DSC and TGA. The degree of randomness determined by 1H-NMR is less than one, thus indicating that these copolyesters have a character to block. All copolyesters were amorphous, having glass transition temperatures decreasing with the content of ionic units. The thermal stability of 2,5-PEF-co-PESs was slightly reduced by the incorporation of these units. The liquid water sorption mechanism was also discussed as a function of the composition of the copolymer and the predominant role of the content of sulfonated groups on liquid water uptake was highlighted. Finally, oxidative degradation has again supported the role of sulfonated units, whereas hydrolytic degradation was not influenced by the concentration of sulfonated groups. By leveraging on their characteristics, 2,5-PEF-co-PESs copolyesters may be can serve as attractive and innovative bio-polymers for practical applications such as textile and membrane…
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References
Vilela C, Sousa AF, Fonseca AC, Serra AC, Coelho JFJ, Freire CSR, Silvestre AJD (2014) The quest for sustainable polyesters – insights into the future. Polym Chem 5:3119–3141. https://doi.org/10.1039/C3PY01213A
Trovatti E, Gonçalves IG, Carvalho AJ, Gandini A (2020) The contribution of bisfurfurylamine to the development and properties of polyureas. Polym Int. https://doi.org/10.1002/pi.6003
Chuang P-L, Nien Y-H (2019) Synthesis and characterization of maleic anhydride grafted SEBS modified with ethanolamine, 2-amino-2-methyl-1-propanol or glycerine. J Polym Res 26:66. https://doi.org/10.1007/s10965-019-1723-7
Sousa AF, Vilela C, Fonseca AC, Matos M, Freire CSR, Gruter GJM, Coelho JFJ, Silvestre AJD (2015) Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym Chem 6:5961–5983. https://doi.org/10.1039/C5PY00686D
Thiyagarajan S, Pukin A, van Haveren J, Lutz M, van Es DS (2013) Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid: unexpected aspects of the Henkel reaction. RSC Adv 3:15678–15686. https://doi.org/10.1039/C3RA42457J
Cousin T, Galy J, Rousseau A, Dupuy J (2018) Synthesis and properties of polyamides from 2,5-furandicarboxylic acid. J Appl Polym Sci 135:45901. https://doi.org/10.1002/app.45901
Chebbi Y, Kasmi N, Majdoub M, Cerruti P, Scarinzi G, Malinconico M, Dal Poggetto G, Papageorgiou GZ, Bikiaris DN (2019) Synthesis, characterization, and biodegradability of novel fully biobased poly(decamethylene-co-isosorbide 2,5-furandicarboxylate) Copolyesters with enhanced mechanical properties. ACS Sustain Chem Eng 7:5501–5514. https://doi.org/10.1021/acssuschemeng.8b06796
Papadopoulos L, Magaziotis A, Nerantzaki M, Terzopoulou Z, Papageorgiou GZ, Bikiaris DN (2018) Synthesis and characterization of novel poly(ethylene furanoate-co-adipate) random copolyesters with enhanced biodegradability. Polym Degrad Stab 156:32–42. https://doi.org/10.1016/j.polymdegradstab.2018.08.002
Cai X, Yang X, Zhang H, Wang G (2018) Aliphatic-aromatic poly(carbonate-co-ester)s containing biobased furan monomer: synthesis and thermo-mechanical properties. Polymer 134:63–70. https://doi.org/10.1016/j.polymer.2017.11.058
Araujo CF, Nolasco MM, Ribeiro-Claro PJA, Rudić S, Silvestre AJD, Vaz PD, Sousa AF (2018) Inside PEF: chain conformation and dynamics in crystalline and amorphous domains. Macromolecules 51:3515–3526. https://doi.org/10.1021/acs.macromol.8b00192
Matos M, Sousa AF, Fonseca AC, Freire CSR, Coelho JFJ, Silvestre AJD (2014) A new generation of furanic copolyesters with enhanced degradability: poly(ethylene 2,5-furandicarboxylate)-co-poly(lactic acid) copolyesters. Macromol Chem Phys 215:2175–2184. https://doi.org/10.1002/macp.201400175
Hbaieb S, Kammoun W, Delaite C, Abid M, Abid S, el Gharbi R (2015) New Copolyesters containing aliphatic and bio-based Furanic units by bulk Copolycondensation. J Macromol Sci A 52:365–373. https://doi.org/10.1080/10601325.2015.1018807
Gomes M, Gandini A, Silvestre AJD, Reis B (2011) Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols. J Polym Sci A Polym Chem 49:3759–3768. https://doi.org/10.1002/pola.24812
Jiang M, Liu Q, Zhang Q, Ye C, Zhou G (2012) A series of furan-aromatic polyesters synthesized via direct esterification method based on renewable resources. J Polym Sci A Polym Chem 50:1026–1036. https://doi.org/10.1002/pola.25859
Knoop RJI, Vogelzang W, van Haveren J, van Es DS (2013) High molecular weight poly(ethylene-2,5-furanoate); critical aspects in synthesis and mechanical property determination. J Polym Sci A Polym Chem 51:4191–4199. https://doi.org/10.1002/pola.26833
Gandini A, Silvestre AJD, Neto CP, Sousa AF, Gomes M (2009) The furan counterpart of poly(ethylene terephthalate): an alternative material based on renewable resources. J Polym Sci A Polym Chem 47:295–298. https://doi.org/10.1002/pola.23130
Zhu J, Cai J, Xie W, Chen PH, Gazzano M, Scandola M, Gross RA (2013) Poly(butylene 2,5-furan dicarboxylate), a biobased alternative to PBT: synthesis, physical properties, and crystal structure. Macromolecules 46:796–804. https://doi.org/10.1021/ma3023298
Ma J, Yu X, Xu J, Pang Y (2012) Synthesis and crystallinity of poly(butylene 2,5-furandicarboxylate). Polymer 53:4145–4151. https://doi.org/10.1016/j.polymer.2012.07.022
Carman H, Killman J, Crawford E, Jenkins J (2013) Polyester compositions containing furandicarboxylic acid or an Ester thereof and 2,2,4,4-Tetramethyl-1,3.-Cyclobutanediol
Storbeck R, Ballauff M (1993) Synthesis and properties of polyesters based on 2,5-furandicarboxylic acid and 1,4:3,6-dianhydrohexitols. Polymer 34:5003–5006. https://doi.org/10.1016/0032-3861(93)90037-B
Gaddour M, Bougarech A, Abid M, Abid S (2019) Biobased Furano-pyridinic copolyamide-imides preparation, characterization and degradation study. J Polym Res 26:74. https://doi.org/10.1007/s10965-019-1739-z
Zhou W, Wang X, Yang B, Xu Y, Zhang W, Zhang Y, Ji J (2013) Synthesis, physical properties and enzymatic degradation of bio-based poly(butylene adipate-co-butylene furandicarboxylate) copolyesters. Polym Degrad Stab 98:2177–2183. https://doi.org/10.1016/j.polymdegradstab.2013.08.025
Jacquel N, Saint-Loup R, Pascault J-P, Rousseau A, Fenouillot F (2015) Bio-based alternatives in the synthesis of aliphatic–aromatic polyesters dedicated to biodegradable film applications. Polymer 59:234–242. https://doi.org/10.1016/j.polymer.2014.12.021
Wu B, Xu Y, Bu Z, Wu L, Li BG, Dubois P (2014) Biobased poly(butylene 2,5-furandicarboxylate) and poly(butylene adipate-co-butylene 2,5-furandicarboxylate)s: from synthesis using highly purified 2,5-furandicarboxylic acid to thermo-mechanical properties. Polymer 55:3648–3655. https://doi.org/10.1016/j.polymer.2014.06.052
Wu L, Mincheva R, Xu Y, Raquez JM, Dubois P (2012) High molecular weight poly(butylene succinate-co-butylene furandicarboxylate) copolyesters: from catalyzed polycondensation reaction to thermomechanical properties. Biomacromolecules 13:2973–2981. https://doi.org/10.1021/bm301044f
Wang J, Liu X, Zhu J, Jiang Y (2017) Copolyesters based on 2,5-Furandicarboxylic acid (FDCA): effect of 2,2,4,4-Tetramethyl-1,3-Cyclobutanediol units on their properties. Polymers 9:305. https://doi.org/10.3390/polym9090305
Guo X-Y, Gu L-X, Feng X-X (2002) The glass transition, crystallization, and melting characteristics of a class of polyester ionomers. J Appl Polym Sci 86:3660–3666. https://doi.org/10.1002/app.11313
Chisholm BJ, Moore RB, Barber G, Khouri F, Hempstead A, Larsen M, Olson E, Kelley J, Balch G, Caraher J (2002) Nanocomposites derived from sulfonated poly(butylene terephthalate). Macromolecules 35:5508–5516. https://doi.org/10.1021/ma012224n
Chisholm BJ, Sisti L, Soloveichik S, Gillette G (2003) Hydrolytic stability of sulfonated poly(butylene terephthalate). Polymer 44:1903–1910. https://doi.org/10.1016/S0032-3861(02)00932-1
Ishida K, Han S-I, Inoue Y, Im S-S (2005) Novel poly(butylene succinate)-based ionomers with sulfonated succinate units: synthesis, morphology, and the unique nucleation effect on crystallization. Macromol Chem Phys 206:1028–1034. https://doi.org/10.1002/macp.200400474
Colonna M, Berti C, Binassi E, Fiorini M, Karanam S, Brunelle DJ (2010) Nanocomposite of montmorillonite with telechelic sulfonated poly(butylene terephthalate): effect of ionic groups on clay dispersion, mechanical and thermal properties. Eur Polym J 46:918–927. https://doi.org/10.1016/j.eurpolymj.2010.02.003
Bautista M, de Ilarduya AM, Alla A, Muñoz-Guerra S (2013) Sulfonated poly(hexamethylene terephthalate) copolyesters: enhanced thermal and mechanical properties. J Appl Polym Sci 129:3527–3535. https://doi.org/10.1002/app.39108
Bougarech A, Abid M, Gouanvé F, Espuche E, Abid S, el Gharbi R, Fleury E (2013) Synthesis, characterization and water sorption study of new biobased (furanic-sulfonated) copolyesters. Polymer 54:5482–5489. https://doi.org/10.1016/j.polymer.2013.07.072
Bougarech A, Abid M, DaCruz-Boisson F, Abid S, el Gharbi R, Fleury E (2014) Modulation of furanic-sulfonated isophthalic copolyesters properties through diols units control. Eur Polym J 58:207–217. https://doi.org/10.1016/j.eurpolymj.2014.06.018
Bautista M, De Ilarduya AM, Alla A, Muñoz-Guerra S (2015) Poly(butylene succinate) ionomers with enhanced Hydrodegradability. Polymers 7:1232–1247. https://doi.org/10.3390/polym7071232
Kacem YH, Bougarech A, Abid S et al (2019) Fully biobased aliphatic anionic oligoesters: synthesis and properties. In: International Journal of Polymer Science. https://www.hindawi.com/journals/ijps/2019/3186202/. Accessed 4 Apr 2020
Dönmez G, Okutan M, Deligöz H (2019) Blend membranes of sulfonated poly (ether ether ketone) and thermoplastic poly (urethane) for fuel cells. J Polym Res 26:133. https://doi.org/10.1007/s10965-019-1792-7
He Z, Zhang Z, Bi S (2019) Long-range crystal alignment with polymer additive for organic thin film transistors. J Polym Res 26:1–8. https://doi.org/10.1007/s10965-019-1842-1
Asare-Yeboah K, Bi S, He Z, Li D (2016) Temperature gradient controlled crystal growth from TIPS pentacene-poly(α-methyl styrene) blends for improving performance of organic thin film transistors. Org Electron 32:195–199. https://doi.org/10.1016/j.orgel.2016.02.028
Wang X, Wang L, Li H, Tang X, Chang FC (2000) Syntheses of poly(ethylene oxide) polyurethane ionomers. J Appl Polym Sci 77:184–188. https://doi.org/10.1002/(SICI)1097-4628(20000705)77:1<184::AID-APP24>3.0.CO;2-8
Gaona O, Kint DPR, Martínez de Ilarduya A et al (2003) Preparation and hydrolytic degradation of sulfonated poly(ethylene terephthalate) copolymers. Polymer 44:7281–7289. https://doi.org/10.1016/j.polymer.2003.09.044
Yamadera R, Murano M (1967) The determination of randomness in copolyesters by high resolution nuclear magnetic resonance. J Polym Sci A-1 Polym Chem 5:2259–2268. https://doi.org/10.1002/pol.1967.150050905
Feng Y, Li C (2006) Study on oxidative degradation behaviors of polyesterurethane network. Polym Degrad Stab 91:1711–1716. https://doi.org/10.1016/j.polymdegradstab.2005.12.002
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Bougarech, A., Abid, S. & Abid, M. Poly (ethylene 2,5-furandicarboxylate) ionomers with enhanced liquid water sorption and oxidative degradation. J Polym Res 27, 217 (2020). https://doi.org/10.1007/s10965-020-02194-2
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DOI: https://doi.org/10.1007/s10965-020-02194-2