Copolyesters developed from bio‐based 2,5‐furandicarboxylic acid: Synthesis, sequence distribution, mechanical, and barrier properties of poly(propylene‐ co ‐1,4‐cyclohexanedimethylene 2,5‐furandicarboxylate)s

Jia, Zhen; Wang, Jinggang; Sun, Liyuan; Liu, Fei; Zhu, Jin; Liu, Xiaoqing

doi:10.1002/app.47291

Title: Copolyesters developed from bio‐based 2,5‐furandicarboxylic acid: Synthesis, sequence distribution, mechanical, and barrier properties of poly(propylene‐ co ‐1,4‐cyclohexanedimethylene 2,5‐furandicarboxylate)s

Journal Article · Sun Nov 25 00:00:00 EST 2018 · Journal of Applied Polymer Science

DOI:https://doi.org/10.1002/app.47291· OSTI ID:1483321

Jia, Zhen ^[1]; Wang, Jinggang ^[1]; Sun, Liyuan ^[2]; Liu, Fei ^[1]; Zhu, Jin ^[1];

^[1]

Ningbo Institute of Materials Technology and Engineering Chinese Academy of Sciences Ningbo Zhejiang 315201 People's Republic of China, Key Laboratory of Bio‐based Polymeric Materials Ningbo Zhejiang 315201 People's Republic of China
Ningbo Institute of Materials Technology and Engineering Chinese Academy of Sciences Ningbo Zhejiang 315201 People's Republic of China, Key Laboratory of Bio‐based Polymeric Materials Ningbo Zhejiang 315201 People's Republic of China, University of Chinese Academy of Sciences Huairou Beijing 100049 People's Republic of China

ABSTRACT A series of poly(propylene‐ co ‐1,4‐cyclohexanedimethylene 2,5‐furandicarboxylate)s (PPCFs) with different compositions were synthesized from bio‐based aromatic monomer 2,5‐furandicarboxylic acid and 1,3‐propanediol (PDO), along with 1,4‐cyclohexanedimethylene (CHDM). The chemical structure, composition, and sequence distribution of PPCFs were determined by nuclear magnetic resonance ( ¹ H NMR and ¹³ C NMR). Results showed that the compositions of copolyesters depended on the feed molar ratio of PDO and CHDM, and all the obtained PPCFs copolyesters had triad component in a random sequential structure. With the addition of CHDM, the gas barrier properties of poly(propylene 2,5‐furandicarboxylate) (PPF) deteriorated. However, when the content of CHDM reached 79%, PPCF79 still showed the CO ₂ and O ₂ barrier improvement factor of 4.5 and 3.25, respectively, which were better than those of poly(ethylene naphthalate), a well‐known polymer with barrier property. Besides, PPCF79 showed good performance on tensile modulus, tensile strength, elongation at break, and the crystallization enthalpy was improved from 3.2 J g ⁻¹ for PPF to 30.7 J g ⁻¹ for PPCF79. It has the potential to serve as a promising bio‐based polymer with excellent comprehensive performance. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019 , 136 , 47291.

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Sponsoring Organization:: USDOE

OSTI ID:: 1483321

Journal Information:: Journal of Applied Polymer Science, Journal Name: Journal of Applied Polymer Science Vol. 136 Journal Issue: 13; ISSN 0021-8995

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 18 works

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References (36)

Modification of poly(ethylene 2,5-furandicarboxylate) (PEF) with 1, 4-cyclohexanedimethanol: Influence of stereochemistry of 1,4-cyclohexylene units Wang, Jinggang; Liu, Xiaoqing; Jia, Zhen Polymer, Vol. 137 https://doi.org/10.1016/j.polymer.2018.01.021	journal	February 2018
Synthesis and structure – property relationship of biobased poly(butylene 2,5-furanoate) – block – (dimerized fatty acid) copolymers Kwiatkowska, Magdalena; Kowalczyk, Inez; Kwiatkowski, Konrad Polymer, Vol. 130 https://doi.org/10.1016/j.polymer.2017.10.009	journal	November 2017
High Molecular Weight Polyesters Derived from Biobased 1,5-Pentanediol and a Variety of Aliphatic Diacids: Synthesis, Characterization, and Thermo-Mechanical Properties Lu, Jing; Wu, Linbo; Li, Bo-Geng ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7 https://doi.org/10.1021/acssuschemeng.7b01050	journal	June 2017
Synthesis of poly(ethylene furandicarboxylate) polyester using monomers derived from renewable resources: thermal behavior comparison with PET and PEN Papageorgiou, George Z.; Tsanaktsis, Vasilios; Bikiaris, Dimitrios N. Phys. Chem. Chem. Phys., Vol. 16, Issue 17 https://doi.org/10.1039/C4CP00518J	journal	January 2014
Copolyesters Based on 2,5-Furandicarboxylic Acid (FDCA): Effect of 2,2,4,4-Tetramethyl-1,3-Cyclobutanediol Units on Their Properties Wang, Jinggang; Liu, Xiaoqing; Zhu, Jin Polymers, Vol. 9, Issue 12 https://doi.org/10.3390/polym9090305	journal	August 2017
Biobased furandicarboxylic acids (FDCAs): effects of isomeric substitution on polyester synthesis and properties Thiyagarajan, Shanmugam; Vogelzang, Willem; J. I. Knoop, Rutger Green Chem., Vol. 16, Issue 4 https://doi.org/10.1039/C3GC42184H	journal	January 2014
Furan-based co-polyesters with enhanced thermal properties: poly(1,4-butylene-co-1,4-cyclohexanedimethylene-2,5-furandicarboxylic acid) Diao, Lechen; Su, Kunmei; Li, Zhenhuan RSC Advances, Vol. 6, Issue 33 https://doi.org/10.1039/C5RA27617A	journal	January 2016
Synthesis of the bio-based polyester poly(propylene 2,5-furan dicarboxylate). Comparison of thermal behavior and solid state structure with its terephthalate and naphthalate homologues Papageorgiou, George Z.; Papageorgiou, Dimitrios G.; Tsanaktsis, Vasilios Polymer, Vol. 62 https://doi.org/10.1016/j.polymer.2015.01.080	journal	April 2015
Antiplasticization-based enhancement of poly(ethylene terephthalate) barrier properties Lee, Jong Suk; Leisen, Johannes; Choudhury, Rudra Prosad Polymer, Vol. 53, Issue 1 https://doi.org/10.1016/j.polymer.2011.11.006	journal	January 2012
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr300182k	journal	February 2013
Modification of poly(ethylene 2,5-furandicarboxylate) with 1,4-cyclohexanedimethylene: Influence of composition on mechanical and barrier properties Wang, Jinggang; Liu, Xiaoqing; Zhang, Yajie Polymer, Vol. 103 https://doi.org/10.1016/j.polymer.2016.09.030	journal	October 2016
Ductile PLA modified with methacryloyloxyalkyl isocyanate improves mechanical properties Chen, Bor-Kuan; Shen, Chia-Hsu; Chen, Shu-Chuan Polymer, Vol. 51, Issue 21 https://doi.org/10.1016/j.polymer.2010.08.028	journal	October 2010
Tailored design of renewable copolymers based on poly(1,4-butylene 2,5-furandicarboxylate) and poly(ethylene glycol) with refined thermal properties Sousa, A. F.; Guigo, N.; Pożycka, M. Polymer Chemistry, Vol. 9, Issue 6 https://doi.org/10.1039/C7PY01627A	journal	January 2018
Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance Eerhart, A. J. J. E.; Faaij, A. P. C.; Patel, M. K. Energy & Environmental Science, Vol. 5, Issue 4 https://doi.org/10.1039/c2ee02480b	journal	January 2012
Fully biobased multiblock copolymers of furan-aromatic polyester and dimerized fatty acid: Synthesis and characterization Kwiatkowska, Magdalena; Kowalczyk, Inez; Kwiatkowski, Konrad Polymer, Vol. 99 https://doi.org/10.1016/j.polymer.2016.07.060	journal	September 2016
Sustainable Aromatic Copolyesters via Ring Opening Polymerization: Poly(butylene 2,5-furandicarboxylate- co -terephthalate)s Morales-Huerta, Juan Carlos; Martínez de Ilarduya, Antxon; Muñoz-Guerra, Sebastián ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 9 https://doi.org/10.1021/acssuschemeng.6b01302	journal	July 2016
Biobased multiblock copolymers: Synthesis, properties and shape memory performance of poly(ethylene 2,5-furandicarboxylate)- b -poly(ethylene glycol) Wang, Guoqiang; Jiang, Min; Zhang, Qiang Polymer Degradation and Stability, Vol. 144 https://doi.org/10.1016/j.polymdegradstab.2017.07.032	journal	October 2017
Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA) Deng, Jun; Liu, Xiaoqing; Li, Chao RSC Advances, Vol. 5, Issue 21 https://doi.org/10.1039/C5RA00242G	journal	January 2015
Urethanes and polyurethanes bearing furan moieties. 4. Synthesis, kinetics and characterization of linear polymers Boufi, Sami; Belgacem, Mohamed Naceur; Quillerou, Joel Macromolecules, Vol. 26, Issue 25 https://doi.org/10.1021/ma00077a003	journal	December 1993
Isomorphism in Poly(butylene succinate- co -butylene fumarate) and Its Application as Polymeric Nucleating Agent for Poly(butylene succinate) Ye, Hai-Mu; Wang, Rui-Dong; Liu, Jin Macromolecules, Vol. 45, Issue 14 https://doi.org/10.1021/ma300685f	journal	July 2012
Fast Crystallization and Melting Behavior of a Long-Spaced Aliphatic Furandicarboxylate Biobased Polyester, Poly(dodecylene 2,5-furanoate) Papageorgiou, Dimitrios G.; Guigo, Nathanael; Tsanaktsis, Vasilios Industrial & Engineering Chemistry Research, Vol. 55, Issue 18 https://doi.org/10.1021/acs.iecr.6b00811	journal	April 2016
Synthesis, physical properties and enzymatic degradation of bio-based poly(butylene adipate-co-butylene furandicarboxylate) copolyesters Zhou, Weidong; Wang, Xiaowei; Yang, Bing Polymer Degradation and Stability, Vol. 98, Issue 11 https://doi.org/10.1016/j.polymdegradstab.2013.08.025	journal	November 2013
Aerobic Oxidation of p-Toluic Acid to Terephthalic Acid over T(p-Cl)PPMnCl/Co(OAc)2 Under Moderate Conditions Xiao, Y.; Luo, W. P.; Zhang, X. Y. Catalysis Letters, Vol. 134, Issue 1-2 https://doi.org/10.1007/s10562-009-0227-1	journal	November 2009
Fully bio-based poly(propylene succinate-co-propylene furandicarboxylate) copolyesters with proper mechanical, degradation and barrier properties for green packaging applications Hu, Han; Zhang, Ruoyu; Wang, Jinggang European Polymer Journal, Vol. 102 https://doi.org/10.1016/j.eurpolymj.2018.03.009	journal	May 2018
A series of furan-aromatic polyesters synthesized via direct esterification method based on renewable resources Jiang, Min; Liu, Qian; Zhang, Qiang Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 5 https://doi.org/10.1002/pola.25859	journal	December 2011
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 Wu, Binshuang; Xu, Yutao; Bu, Zhiyang Polymer, Vol. 55, Issue 16 https://doi.org/10.1016/j.polymer.2014.06.052	journal	August 2014
Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid: unexpected aspects of the Henkel reaction Thiyagarajan, Shanmugam; Pukin, Aliaksei; van Haveren, Jacco RSC Adv., Vol. 3, Issue 36 https://doi.org/10.1039/C3RA42457J	journal	January 2013
Synthesis and characterization of furanic polyamides Mitiakoudis, Anastassios; Gandini, Alessandro Macromolecules, Vol. 24, Issue 4 https://doi.org/10.1021/ma00004a003	journal	July 1991
The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources Gandini, Alessandro; Silvestre, Armando J. D.; Neto, Carlos Pascoal Journal of Polymer Science Part A: Polymer Chemistry, Vol. 47, Issue 1 https://doi.org/10.1002/pola.23130	journal	January 2009
Synthesis and Characterization of Bio-Based Polyesters: Poly(2-methyl-1,3-propylene-2,5-furanoate), Poly(isosorbide-2,5-furanoate), Poly(1,4-cyclohexanedimethylene-2,5-furanoate) Terzopoulou, Zoi; Kasmi, Nejib; Tsanaktsis, Vasilios Materials, Vol. 10, Issue 7 https://doi.org/10.3390/ma10070801	journal	July 2017
Crystallization and Polymorphism of Poly(ethylene furanoate) Tsanaktsis, Vasilios; Papageorgiou, Dimitrios G.; Exarhopoulos, Stylianos Crystal Growth & Design, Vol. 15, Issue 11 https://doi.org/10.1021/acs.cgd.5b01136	journal	October 2015
A facile method to synthesize high-molecular-weight biobased polyesters from 2,5-furandicarboxylic acid and long-chain diols Tsanaktsis, Vasilios; Papageorgiou, George Z.; Bikiaris, Dimitrios N. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 22 https://doi.org/10.1002/pola.27730	journal	June 2015
High molecular weight bio furan-based co-polyesters for food packaging applications: synthesis, characterization and solid-state polymerization Hong, Sungmin; Min, Kyung-Deok; Nam, Byeong-Uk Green Chemistry, Vol. 18, Issue 19 https://doi.org/10.1039/C6GC01060A	journal	January 2016
Polyol Structure Influences Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Polyesters Haernvall, Karolina; Zitzenbacher, Sabine; Amer, Hassan Biotechnology Journal, Vol. 12, Issue 9 https://doi.org/10.1002/biot.201600741	journal	August 2017
Conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Au-based catalysts: Optimization of active phase and metal–support interaction Albonetti, Stefania; Lolli, Alice; Morandi, Vittorio Applied Catalysis B: Environmental, Vol. 163 https://doi.org/10.1016/j.apcatb.2014.08.026	journal	February 2015
Furan-based polyesters from renewable resources: Crystallization and thermal degradation behavior of poly(hexamethylene 2,5-furan-dicarboxylate) Papageorgiou, George Z.; Tsanaktsis, Vasilios; Papageorgiou, Dimitrios G. European Polymer Journal, Vol. 67 https://doi.org/10.1016/j.eurpolymj.2014.08.031	journal	June 2015

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