Bio-based poly(butylene furandicarboxylate-co-butylene 2,5-thiophenedicarboxylate): synthesis, thermal properties, crystallization properties and mechanical properties

Wang, Guoqiang; Dong, Yakun; Hao, Xingyu; Zhang, Li; Sun, Rubo

doi:10.1007/s00289-022-04330-y

Cited by 13 publications

(11 citation statements)

References 43 publications

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“…Obviously, the average molecular weight (M w ) of PBFTF (20 700−41 400 g•mol −1 ) was reduced with increasing 2,5-thiophenedicarboxylic acid (2,5-TDCA) content. 57 In this case, 2,5-TDCA is less acidic than 2,5-FDCA, resulting in less active 2,5-TDCA. In addition, the molecular weights of both polyesters (PBF and PBTF) were higher than those of PBFTF, indicating that 2,5-TDCA and 2,5-FDCA had a weaker tendency to copolymerize and a higher tendency to homopolymerize.…”

Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 98%

“…211−217 Correspondingly, the average molecular weight (M w ) (30 000−70 000 g•mol −1 ) and polymorphism (ID) data are presented in Table 10. 57 Moreover, PBF exhibited the maximum molecular weight (M w ) (67 000 g•mol −1 ), which could be owing to the strong acidity of 2,5-FDCA. Obviously, the average molecular weight (M w ) of PBFTF (20 700−41 400 g•mol −1 ) was reduced with increasing 2,5-thiophenedicarboxylic acid (2,5-TDCA) content.…”

Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 99%

“…The synthesis of 2,5-furandicarboxylic acid (2,5-FDCA)-based homo-and copolyesters such as PBF, PBTF, and PBFTFs polyesters using BDO, FDCA, and TDCA through esterification and polycondensation approaches is shown in Scheme 12. 57 After the synthesis of those polyesters, structural property analysis is necessary. From our literature survey, we observed that most authors determined the molecular weight by gel permeation chromatography up to 2023.…”

Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 99%

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Recent Progress on Sustainable 2,5-Furandicarboxylate-Based Polyesters: Properties and Applications

Miah,

Dong,

Wang

et al. 2024

ACS Sustainable Chem. Eng.

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Polyesters based on 2,5-furandicarboxylic acid (2,5-FDCA) have attracted attention from both academia and industry as a new class of biobased polymers for the growing era of plastics. 2,5-FDCA-based polyesters are 100% renewable, and they are an alternative to petroleum-based or terephthalic acid (TPA)-based polyesters. Moreover, scientists and plastics experts have recognized bioplastics as an eco-friendly solution to developing cost-effective renewable plastics. The growth of the bioplastics market depends on a sustainable economy, population growth, and rapid changes in different polymers. Although a variety of auxiliaries have been practically used in recent years, the production of bioplastics from 2,5-FDCA monomers by oxidation of 5-hydroxymethylfurfural (HMF) is a relatively innovative field of research. This review focuses on the properties and applications of 2,5-FDCA-based polyesters in the packaging and coating industries for producing biobased postconsumer products. The manufacturability, excellent (thermal, mechanical, and barrier) features, and applications in various fields of available 2,5-FDCAbased homo-and copolyesters are discussed. Biobased 2,5-FDCA pure homo-and copolyesters have recently progressed with exceptional properties for their counterparts petroleum-based polyesters. In particular, the mechanical performance of 2,5-FDCAbased pure homopolyesters such as poly(ethylene 2,5-furandicarboxylate) (PEF) and poly(propylene 2,5-furandicarboxylate) (PPF) has the highest tensile strength (σ b ) values of 84.07 ± 4.43 and 90 ± 6 MPa, respectively, compared with other homopolyesters. On the other hand, 2,5-FDCA-based neat copolyesters like poly(ethylene 2,5-thiophenedicarboxylate) (PETF) and poly(ethylene-co-1,4-cyclohexanedimethylene 2,5-furandicarboxylate) (PECF) had maximum tensile strength (σ b ) values of 97−98 and 59−75 MPa, respectively, compared to other copolyesters. In addition, we also compared and observed the highest Young's modulus (E) values of pure PEF (5248 ± 328 MPa) and pure PPF (2460 ± 280 MPa) homopolyesters and of neat PETF (3100−3300 MPa) and neat PECF (1740−2300 MPa) copolyesters. Furthermore, the elongation at break (ε b ) values of pure poly(decylene furandicarboxylate) (PDF) (986 ± 82%) and pure poly(butylene 2,5-furandicarboxylate) (PBF) (368 ± 43%) homopolyesters and neat poly(pentylene furandicarboxylate) (PPeF) (1050 ± 200%) and neat poly(1,4-butanediol 2,5-thiophenedicarboxylate) (PBTF) (900 ± 84%) copolyesters had the highest values compared to other pure homo-and copolyesters. Finally, the results of the barrier improvement factor (BIFp) study showed that neat PPeF copolyesters had the highest values of O 2 (227 BIFp) and CO 2 (979 BIFp) compared to other pure homo-and copolyesters.

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Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 98%

Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 99%

Section: Features Of 25-fdca-based Homo-and Copolyestersmentioning

confidence: 99%

See 1 more Smart Citation

Recent Progress on Sustainable 2,5-Furandicarboxylate-Based Polyesters: Properties and Applications

Miah,

Dong,

Wang

et al. 2024

ACS Sustainable Chem. Eng.

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“…Therefore, the utilization of TDCA will probably lead to a class of novel copolyesters suitable for packaging applications that demand a high barrier as substitutes for the commodity PBAT. However, previous studies have mainly focused on nondegradable TDCA-based homopolyesters, including PPTh, , poly(butylene thiophenedicarboxylate) (PBTh), ,,,, poly(pentylene thiophenedicarboxylate) (PPeTh), and copolyesters containing other monomers such as FDCA, PTA, , 1,4-cyclohexanedimethanol (CHDM), , and 2,6-naphthalenedicarboxylic acid (2,6-NDCA) . There were only a few attempts at the investigation of TDCA-based biodegradable polyesters. , Guidotti et al prepared poly(butylene adipate/2,5-thiophenedicarboxylate) (PBA x TF y ) copolyesters by inserting adipic acid units into PBTh, and after 73 days of a compost experiment, PBA 90 TF 10 containing 10 mol % of TDCA reached 100% weight loss .…”

Section: Introductionmentioning

confidence: 99%

Biobased Biodegradable Copolyesters from 2,5-Thiophenedicarboxylic Acid: Effect of Aliphatic Diols on Barrier Properties and Degradation

Wang,

Li,

Wang

et al. 2023

Biomacromolecules

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The demand for sustainable development has led to increasing attention in biobased polyesters due to their adjustable thermal and mechanical properties and biodegradability. In this study, we used a novel bioderived aromatic diacid, 2,5-thiophenedicarboxylic acid (TDCA) to synthesize a list of novel aromatic–aliphatic poly(alkylene adipate-co-thiophenedicarboxylate) (PAATh) copolyesters through a facile melt polycondensation method. PAAThs are random copolyesters with weight-average molecular weights of 58400 to 84200 g·mol–1 and intrinsic viscosities of 0.80 to 1.27 dL·g–1. All PAAThs exhibit sufficiently high thermal stability as well as the highest tensile strength of 6.2 MPa and the best gas barrier performances against CO2 and O2, 4.3- and 3.3-fold better than those of poly(butylene adipate-co-terephthalate) (PBAT). The biodegradability of PAAThs was fully evaluated through a degradation experiment and various experimental parameters, including residue weights, surface morphology, and molecular compositions. The state-of-the-art molecular dynamics (MD) simulations were applied to elucidate the different enzymatic degradation behaviors of PAAThs due to the effect of diols with different chain structures. The sterically hindered carbonyl carbon of the PHATh–enzyme complex was more susceptible to nucleophilic attack and exhibited a higher tendency to enter a prereaction state. This study has introduced a group of novel biobased copolyesters with their structure–property relationships investigated thoroughly, and the effect of diol components on the enzymatic degradation was revealed by computational analysis. These findings may lay the foundation for the development of promising substitutes for commercial biodegradable polyesters and shed light on their complicated degradation mechanisms.

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“…2,5‐Thiophenedicarboxylic acid (TDCA) can be synthesized by adipic acid and sulfoxide chloride, 28–30 since adipic acid has been prepared from renewable resources, TDCA is a potentially bio‐based monomer. Due to the similar chemical structure to terephthalic acid and 2,5‐furandicarboxylic acid (FDCA), TDCA may possess the same application scenario as them, thus it has been also used to develop various polyesters 31 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of dioctyl 2,5‐thiophenedicarboxylate as a potentially bio‐based plasticizer for poly(vinyl chloride)

Meng,

Dong,

Yang

et al. 2023

J of Applied Polymer Sci

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In this work, dioctyl 2,5‐thiophenedicarboxylate (DOT), a potentially bio‐based plasticizer, was synthesized and evaluated as an alternative to traditional petroleum‐based plasticizers. The chemical structure of DOT was confirmed by FTIR and 1H NMR. Besides, its plasticization effect on poly(vinyl chloride) (PVC) was investigated in detail, and dioctyl 2,5‐furandicarboxylate (DOF) as well as dioctyl isophthalate (DOIP) with similar chemical structures were used as references. The DMA results showed that the glass transition temperature (Tg) of PVC/DOT, PVC/DOF, and PVC/DOIP was 45.1°C, 33.6°C, and 51.3°C, respectively, indicating that the plasticizing efficiency of DOT was better than that of DOIP but lower than that of DOF. However, the tensile test results exhibited that the elongation at the break of PVC/DOT was higher than that of PVC/DOF, which was attributed to the easy phase separation between DOF and PVC. In addition, DOT displayed the best volatility resistance and exudation resistance among the three plasticizers, attributed to its highest molecular weight. Moreover, the migration loss of DOT in non‐polar solvents was much smaller than that of DOIP because of its stronger molecular polarity. In conclusion, DOT has good potential to replace traditional petroleum‐based plasticizers and be used as a primary plasticizer for PVC.

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Bio-based poly(butylene furandicarboxylate-co-butylene 2,5-thiophenedicarboxylate): synthesis, thermal properties, crystallization properties and mechanical properties

Cited by 13 publications

References 43 publications

Recent Progress on Sustainable 2,5-Furandicarboxylate-Based Polyesters: Properties and Applications

Recent Progress on Sustainable 2,5-Furandicarboxylate-Based Polyesters: Properties and Applications

Biobased Biodegradable Copolyesters from 2,5-Thiophenedicarboxylic Acid: Effect of Aliphatic Diols on Barrier Properties and Degradation

Synthesis and evaluation of dioctyl 2,5‐thiophenedicarboxylate as a potentially bio‐based plasticizer for poly(vinyl chloride)

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