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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

Abstract

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.

Authors:
 [1];  [1];  [2];  [1];  [1]; ORCiD logo [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
  2. 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
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1483321
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Journal of Applied Polymer Science
Additional Journal Information:
Journal Name: Journal of Applied Polymer Science Journal Volume: 136 Journal Issue: 13; Journal ID: ISSN 0021-8995
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
United States
Language:
English

Citation Formats

Jia, Zhen, Wang, Jinggang, Sun, Liyuan, Liu, Fei, Zhu, Jin, and Liu, Xiaoqing. 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. United States: N. p., 2018. Web. doi:10.1002/app.47291.
Jia, Zhen, Wang, Jinggang, Sun, Liyuan, Liu, Fei, Zhu, Jin, & Liu, Xiaoqing. 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. United States. https://doi.org/10.1002/app.47291
Jia, Zhen, Wang, Jinggang, Sun, Liyuan, Liu, Fei, Zhu, Jin, and Liu, Xiaoqing. Sun . "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". United States. https://doi.org/10.1002/app.47291.
@article{osti_1483321,
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},
author = {Jia, Zhen and Wang, Jinggang and Sun, Liyuan and Liu, Fei and Zhu, Jin and Liu, Xiaoqing},
abstractNote = {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.},
doi = {10.1002/app.47291},
journal = {Journal of Applied Polymer Science},
number = 13,
volume = 136,
place = {United States},
year = {Sun Nov 25 00:00:00 EST 2018},
month = {Sun Nov 25 00:00:00 EST 2018}
}

Journal Article:
Free Publicly Available Full Text
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https://doi.org/10.1002/app.47291

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Cited by: 18 works
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Works referenced in this record:

Synthesis of poly(ethylene furandicarboxylate) polyester using monomers derived from renewable resources: thermal behavior comparison with PET and PEN
journal, January 2014

  • Papageorgiou, George Z.; Tsanaktsis, Vasilios; Bikiaris, Dimitrios N.
  • Phys. Chem. Chem. Phys., Vol. 16, Issue 17
  • DOI: 10.1039/C4CP00518J

Biobased furandicarboxylic acids (FDCAs): effects of isomeric substitution on polyester synthesis and properties
journal, January 2014

  • Thiyagarajan, Shanmugam; Vogelzang, Willem; J. I. Knoop, Rutger
  • Green Chem., Vol. 16, Issue 4
  • DOI: 10.1039/C3GC42184H

Antiplasticization-based enhancement of poly(ethylene terephthalate) barrier properties
journal, January 2012


Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources
journal, February 2013

  • van Putten, Robert-Jan; van der Waal, Jan C.; de Jong, Ed
  • Chemical Reviews, Vol. 113, Issue 3
  • DOI: 10.1021/cr300182k

Ductile PLA modified with methacryloyloxyalkyl isocyanate improves mechanical properties
journal, October 2010


Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance
journal, January 2012

  • Eerhart, A. J. J. E.; Faaij, A. P. C.; Patel, M. K.
  • Energy & Environmental Science, Vol. 5, Issue 4
  • DOI: 10.1039/c2ee02480b

Fully biobased multiblock copolymers of furan-aromatic polyester and dimerized fatty acid: Synthesis and characterization
journal, September 2016


Sustainable Aromatic Copolyesters via Ring Opening Polymerization: Poly(butylene 2,5-furandicarboxylate- co -terephthalate)s
journal, July 2016

  • Morales-Huerta, Juan Carlos; Martínez de Ilarduya, Antxon; Muñoz-Guerra, Sebastián
  • ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 9
  • DOI: 10.1021/acssuschemeng.6b01302

Synthesis and properties of a bio-based epoxy resin from 2,5-furandicarboxylic acid (FDCA)
journal, January 2015

  • Deng, Jun; Liu, Xiaoqing; Li, Chao
  • RSC Advances, Vol. 5, Issue 21
  • DOI: 10.1039/C5RA00242G

Urethanes and polyurethanes bearing furan moieties. 4. Synthesis, kinetics and characterization of linear polymers
journal, December 1993

  • Boufi, Sami; Belgacem, Mohamed Naceur; Quillerou, Joel
  • Macromolecules, Vol. 26, Issue 25
  • DOI: 10.1021/ma00077a003

Fast Crystallization and Melting Behavior of a Long-Spaced Aliphatic Furandicarboxylate Biobased Polyester, Poly(dodecylene 2,5-furanoate)
journal, April 2016

  • Papageorgiou, Dimitrios G.; Guigo, Nathanael; Tsanaktsis, Vasilios
  • Industrial & Engineering Chemistry Research, Vol. 55, Issue 18
  • DOI: 10.1021/acs.iecr.6b00811

Synthesis, physical properties and enzymatic degradation of bio-based poly(butylene adipate-co-butylene furandicarboxylate) copolyesters
journal, November 2013


Aerobic Oxidation of p-Toluic Acid to Terephthalic Acid over T(p-Cl)PPMnCl/Co(OAc)2 Under Moderate Conditions
journal, November 2009


A series of furan-aromatic polyesters synthesized via direct esterification method based on renewable resources
journal, December 2011

  • Jiang, Min; Liu, Qian; Zhang, Qiang
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 5
  • DOI: 10.1002/pola.25859

Concurrent formation of furan-2,5- and furan-2,4-dicarboxylic acid: unexpected aspects of the Henkel reaction
journal, January 2013

  • Thiyagarajan, Shanmugam; Pukin, Aliaksei; van Haveren, Jacco
  • RSC Adv., Vol. 3, Issue 36
  • DOI: 10.1039/C3RA42457J

Synthesis and characterization of furanic polyamides
journal, July 1991

  • Mitiakoudis, Anastassios; Gandini, Alessandro
  • Macromolecules, Vol. 24, Issue 4
  • DOI: 10.1021/ma00004a003

The furan counterpart of poly(ethylene terephthalate): An alternative material based on renewable resources
journal, January 2009

  • Gandini, Alessandro; Silvestre, Armando J. D.; Neto, Carlos Pascoal
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 47, Issue 1
  • DOI: 10.1002/pola.23130

Crystallization and Polymorphism of Poly(ethylene furanoate)
journal, October 2015

  • Tsanaktsis, Vasilios; Papageorgiou, Dimitrios G.; Exarhopoulos, Stylianos
  • Crystal Growth & Design, Vol. 15, Issue 11
  • DOI: 10.1021/acs.cgd.5b01136

A facile method to synthesize high-molecular-weight biobased polyesters from 2,5-furandicarboxylic acid and long-chain diols
journal, June 2015

  • Tsanaktsis, Vasilios; Papageorgiou, George Z.; Bikiaris, Dimitrios N.
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 53, Issue 22
  • DOI: 10.1002/pola.27730

High molecular weight bio furan-based co-polyesters for food packaging applications: synthesis, characterization and solid-state polymerization
journal, January 2016

  • Hong, Sungmin; Min, Kyung-Deok; Nam, Byeong-Uk
  • Green Chemistry, Vol. 18, Issue 19
  • DOI: 10.1039/C6GC01060A

Polyol Structure Influences Enzymatic Hydrolysis of Bio-Based 2,5-Furandicarboxylic Acid (FDCA) Polyesters
journal, August 2017

  • Haernvall, Karolina; Zitzenbacher, Sabine; Amer, Hassan
  • Biotechnology Journal, Vol. 12, Issue 9
  • DOI: 10.1002/biot.201600741

Conversion of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over Au-based catalysts: Optimization of active phase and metal–support interaction
journal, February 2015


Furan-based polyesters from renewable resources: Crystallization and thermal degradation behavior of poly(hexamethylene 2,5-furan-dicarboxylate)
journal, June 2015