New biodegradable polyesters synthesized from 2,5-thiophenedicarboxylic acid with excellent gas barrier properties

Zhang, Xiaoqin; Wang, Jinggang; Wang, Qianfeng; Dong, Yunxiao; Zhu, Jin

doi:10.1016/j.polymdegradstab.2022.110148

Cited by 13 publications

(22 citation statements)

References 48 publications

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“…The concentration of the sample ( c ) in a homogeneous solution, 1,1,2,2-tetrachloroethane/phenol (1/1, w / w ), was about 5 mg/mL. [ η ] was calculated by eq false[ η false] = ( 1 + 1.4 η sp ) 0.5 − 1 0.7 c where η sp is the specific viscosity of the polyester.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure–Property Relationships of Novel High Molecular Weight Fully Biobased 2,5-Thiophenedicarboxylic Acid-Based Polyesters

Tian

Shi

et al. 2023

Biomacromolecules

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High molecular weight fully biobased poly(propylene succinate-co-2,5-thiophenedicarboxylate) (PPSTF) random copolyesters based on the emerging biobased aromatic diacid, 2,5-thiophenedicarboxylic acid (TFDCA), in full composition range were synthesized via melt polycondensation. Their crystallization behavior, thermal-mechanical, gas barrier, and biodegradable properties were systematically investigated. A certain level of comonomer cocrystallization was evidenced by XRD, and PTF units had stronger crystallization competitive capability compared to PS units due to the higher stiffness of TFDCA units. These copolyesters exhibited excellent thermal stability, and mechanical properties can be easily controlled by tuning the varied ratio of flexible to rigid segments. Gas barrier properties were studied from both theoretically calculated and experimental perspectives, and the copolyesters even with 50 mol % PS units still showed superior gas permeation resistance. The selected lipase from Aspergillus oryzae can degrade the copolyesters with up to 60 mol % PTF units. The nonbiodegradable-biodegradable transition was found to occur at the number-average sequence length of aromatic PTF units as low as about 3. Interestingly, when compared with their terephthalic acid-based (TA-based) and 2,5-furandicarboxylic acid-based (FDCA-based) analogues with the same content of aromatic units, the apparent degradation rate constant (k) and half period (t 1/2) of PPSTF60 were actually between them. These findings offer much promise for the application of polyesters containing odd-carbon diol monomers in green packaging and other fields.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Structure–Property Relationships of Novel High Molecular Weight Fully Biobased 2,5-Thiophenedicarboxylic Acid-Based Polyesters

Tian

Shi

et al. 2023

Biomacromolecules

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“…31 There were only a few attempts at the investigation of TDCA-based biodegradable polyesters. 32,33 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. 32 Zhang and co-workers modified PBTh with succinic acid, and the resulting copolyesters exhibited CO 2 barrier properties up to 60.2 times better than PBAT and biodegradability under enzymatic and composting conditions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…32 Zhang and co-workers modified PBTh with succinic acid, and the resulting copolyesters exhibited CO 2 barrier properties up to 60.2 times better than PBAT and biodegradability under enzymatic and composting conditions. 33 Interestingly, previous studies have established that the combinations of 1,4-butanediol (1,4-BDO) with PTA and FDCA formed polyesters with the best crystallization properties among their homologues, and thus, PBAT and PBAF were the most promising copolyesters. On the contrary, the crystallization behaviors of TDCA-based polyesters are quite unique and different from those of PTA and FDCA, since 1,3propanediol (1,3-PDO) seems to be compatible with TDCA than 1,4-BDO in terms of crystallization.…”

Section: ■ Introductionmentioning

confidence: 99%

“…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 . Zhang and co-workers modified PBTh with succinic acid, and the resulting copolyesters exhibited CO 2 barrier properties up to 60.2 times better than PBAT and biodegradability under enzymatic and composting conditions .…”

Section: Introductionmentioning

confidence: 99%

“…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 . Zhang and co-workers modified PBTh with succinic acid, and the resulting copolyesters exhibited CO 2 barrier properties up to 60.2 times better than PBAT and biodegradability under enzymatic and composting conditions . Interestingly, previous studies have established that the combinations of 1,4-butanediol (1,4-BDO) with PTA and FDCA formed polyesters with the best crystallization properties among their homologues, and thus, PBAT and PBAF were the most promising copolyesters.…”

Section: Introductionmentioning

confidence: 99%

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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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Crystallization Kinetics and Melting Behavior of Novel Biobased Poly(butylene 2,5‐thiophenedicarboxylate)

Chen,

Pan,

Qiu

2024

ChemistrySelect

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Poly(butylene 2,5‐thiophenedicarboxylate) (PBTh) is a novel biobased semicrystalline polyester with superior thermal, mechanical, and gas barrier properties; however, the crystallization kinetics and melting behavior of PBTh have not been studied in detail so far. The crystallization kinetics of PBTh was first studied in this research. The Ozawa equation failed to describe the nonisothermal melt crystallization kinetics of PBTh due to the secondary crystallization. The crystallization activation energy value was calculated by the Friedman method, which was negative and exhibited the conversion dependence. The isothermal melt crystallization kinetics of PBTh was well described by the Avrami equation in a wide range of crystallization temperature from 84 to 120 °C. PBTh showed the fastest crystallization rate at 104 °C; moreover, the Avrami exponent value slightly varied between 2.2 and 2.7, suggesting the same crystallization mechanism within the investigated temperature range. PBTh displayed one or two melting endotherms depending on crystallization temperature, which was well explained by the melting, recrystallization, and remelting mechanism. In addition, the equilibrium melting point of PBTh was estimated to be 163.1 °C with the Hoffmann−Weeks equation.

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New biodegradable polyesters synthesized from 2,5-thiophenedicarboxylic acid with excellent gas barrier properties

Cited by 13 publications

References 48 publications

Synthesis and Structure–Property Relationships of Novel High Molecular Weight Fully Biobased 2,5-Thiophenedicarboxylic Acid-Based Polyesters

Synthesis and Structure–Property Relationships of Novel High Molecular Weight Fully Biobased 2,5-Thiophenedicarboxylic Acid-Based Polyesters

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

Crystallization Kinetics and Melting Behavior of Novel Biobased Poly(butylene 2,5‐thiophenedicarboxylate)

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