Copolyesters Based on 2,5-Furandicarboxylic Acid (FDCA) – Copolyesters Furandicarboxylic Acid FDCA - Archive
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Copolyesters Based on 2,5-Furandicarboxylic Acid (FDCA): Effect of 2,2,4,4-Tetramethyl-1,3-Cyclobutanediol Units on Their Properties
Jinggang Wang 1,2, Xiaoqing Liu 1,*, Jin Zhu 1 and Yanhua Jiang 1
1 Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201,
China; wangjg@nimte.ac.cn (J.W.); jzhu@nimte.ac.cn (J.Z.); jyhua@nimte.ac.cn (Y.J.)
2 University of Chinese Academy of Sciences, Beijing 100049, China
* Correspondence: liuxq@nimte.ac.cn; Tel.: +86-574-8668-5925
Received: 24 June 2017; Accepted: 21 July 2017; Published: 24 August 2017
Abstract: Bio-based polyesters derived from 2,5-furandicarboxylic acid (FDCA), including poly(ethylene 2,5-furandicarboxylate) (PEF), poly(propylene 2,5-furandicarboxylate) (PPF), and poly(butylene 2,5-furandicarboxylate) (PBF) have been synthesized and modified with 2,2,4,4-tetramethyl-1,3-cyclobutanediol (CBDO).
Copolyesters with increased glass transition temperature,good barrier and better mechanical properties, as well as higher transparency were reported in this work. The chemical structures, composition, and sequence distribution of the copolyesters were determined by 1H NMR and 13C NMR.
The degree of random (R) was close to 1 for all the copolyesters, indicating their random chemical structures. With the introduction of 10% CBDO units, the semi-crystalline PEF and PPF were changed into completely amorphous polyesters and the higher transparency was easily achieved. The glass transition temperature was increased from 87 C for PEF to 91.1 C for PETF-18, from 55.5 C for PPF to 63.5 C for PPTF-18, and from 39.0 C for PBF to 43.5 C for PBTF-18. The barrier properties investigation demonstrated that although the O2 and CO2 barrier of PEF/PPF/PBF were decreased by the addition of CBDO units, the modified copolyesters still showed good barrier properties.
Keywords: 2,5-Furandicarboxylic acid (FDCA); poly (ethylene 2,5-furandicarboxylate) (PEF); poly(propylene 2,5-furandicarboxylate) (PPF); poly(butylene 2,5-furandicarboxylate) (PBF); 2,2,4,4- tetramethyl-1,3-cyclobutanediol (CBDO)
1. Introduction
In recent years, due to diminishing crude oil reserves and worsening environmental pollution, more and more attention has been paid to the synthesis of polymers derived from renewable resources to replace the petroleum-based ones. However, their thermal or mechanical properties are still subject to improvement when compared with the petroleum-based engineering plastics like poly(ethylene terephthalate) (PET) and polycarbonate (PC) [1–3].
The lack of aromatic or rigid segments in their molecular architecture should be responsible for the relatively low performance. Therefore, exploring
the new bio-based platform chemicals with unique structures and then developing polymeric materials with a higher performance–price ratio is always a matter of importance.
2,5-furandicarboxylic acid (FDCA) is exactly the promising bio-based platform chemical, which can be derived from cellulose or hemicellulose. It has been selected as one of the top 12 value-added chemicals derived from biomass by the US Department of Energy. It is also referred to as a “sleeping giant” by DuPont and DSM due to its great potential as a bio-based substitute for terephthalate (TPA) [4]. In fact, as early as 1940s, the FDCA-based polymers had been firstly reported in Celanese’s work.
