High performance sulfur-containing copolyesters from bio-sourced aromatic monomers

Djouonkep, Lesly Dasilva Wandji; Cheng, Zhengzai; Siegu, William Mawuko Kodjo; Jing, X.B.; Adom, Elvis Kwame; Muaz, A. K. M.; Gauthier, Mario

doi:10.3144/expresspolymlett.2022.8

Cited by 10 publications

(10 citation statements)

References 42 publications

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“…Dimethyl 2,5-thiophenedicarboxylate (DMTD, purity > 98% ) was synthesized as described by Wang et al [ 46 ]. The synthesis of dimethyl 2,5-dimethoxyterephthalate (DMDMT, purity > 98%) was described in our previous work [ 47 ]. Methanol, ethanol, dimethylformamide, chloroform, and Pseudomonas fluorescens enzymatic solution with an activity above 50 U/mL were purchased from the Wuhan Squire Test Agent Liability Co. All the chemicals were used as received without further purification.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous research [ 47 ], we investigated the synthesis and the characterization of a series of thiophene–aromatic copolyesters obtained with a 1:1 molar ratio of DMTD and DMDMT, while varying the diol chain length in the copolyester backbone. Despite their good thermal and mechanical properties, the degradability of the copolyesters under composting conditions was low.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

et al. 2022

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In this work, the feasibility of replacing petroleum-based poly(ethylene terephthalate) (PET) with fully bio-based copolyesters derived from dimethyl 2,5-thiophenedicarboxylate (DMTD), dimethyl 2,5-dimethoxyterephthalate (DMDMT), and polysaccharide-derived 1,6-hexanediol (HDO) was investigated. A systematic study of structure-property relationship revealed that the properties of these poly(thiophene–aromatic) copolyesters (PHS(20–90)) can be tailored by varying the ratio of diester monomers in the reaction, whereby an increase in DMTD content noticeably shortened the reaction time in the transesterification step due to its higher reactivity as compared with DMDMT. The copolyesters had weight-average molar masses (Mw) between 27,500 and 38,800 g/mol, and dispersity Đ of 2.0–2.5. The different polarity and stability of heterocyclic DMTD provided an efficient mean to tailor the crystallization ability of the copolyesters, which in turn affected the thermal and mechanical performance. The glass transition temperature (Tg) could be tuned from 70–100 °C, while the tensile strength was in a range of 23–80 MPa. The obtained results confirmed that the co-monomers were successfully inserted into the copolyester chains. As compared with commercial poly(ethylene terephthalate), the copolyesters displayed not only enhanced susceptibility to hydrolysis, but also appreciable biodegradability by lipases, with weight losses of up to 16% by weight after 28 weeks of incubation.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

et al. 2022

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“…The O 2 barrier improvement factor (BIFp) was calculated by dividing the O 2 permeability coefficient of the target polymer by the O 2 permeability coefficient of PET over a period of 70 days. From previous studies [ 45 , 65 ], the thiophene ring, owing to its asymmetric rigid structure and lower dipole moment of 0.51D, significantly impacted the gas barrier properties of polyesters compared to furan (dipole moment of 0.70D). Herein, PTB 50 H 50 displayed the lowest permeability to O 2 and CO 2 , with a coefficient value of 0.47 and 3.02, respectively, attributed to its high molecular weight and T g value.…”

Section: Resultsmentioning

confidence: 99%

“…They found that the higher the 1,6-HDO moieties, the faster the degradation rate in soil under passive or enzymatic degradation. Djouonkep and coworkers [ 30 , 45 ], as well as Wang et al [ 44 , 46 ], systematically synthesized a series of bio-based polyesters from TDCA, each incorporating 3–8 methylene chain-length diols. They noticed that the polyesters’ chain mobility and morphology strongly depended on 1,6-HDO mole ratios added at the polymerization stage to tune the material properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties

et al. 2023

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Volatile global oil prices, owing to the scarcity of fossil resources, have impacted the cost of producing petrochemicals. Therefore, there is a need to seek novel, renewable chemicals from biomass feedstocks that have comparable properties to petrochemicals. In this study, synthesis, thermal and mechanical properties, and degradability studies of a novel series of sustainable thiophene-based copolyesters like poly(hexylene 2,5-thiophenedicarboxylate-co-bis(2-hydroxyethoxybenzene) (PTBxHy) were conducted via a controlled melt polymerization method. Fourier-transform infrared (FTIR) and nuclear magnetic resonance (1H NMR) spectroscopy techniques elucidated the degree of randomness and structural properties of copolyesters. Meanwhile, gel permeation chromatography (GPC) analysis showed a high average molecular weight in the range of 67.4–78.7 × 103 g/mol. The glass transition temperature (Tg) was between 69.4 and 105.5 °C, and the melting point between 173.7 and 194.2 °C. The synthesized polymers outperformed poly(ethylene 2,5-thiophenedicarboxylate) (PETF) and behaved similarly to poly(ethylene terephthalate) (PET). The copolyesters exhibited a high tensile strength of 46.4–70.5 MPa and a toughness of more than 600%, superior to their corresponding homopolyesters. The copolyesters, which ranged from 1,4-bis(2-hydroxyethyl)benzene thiophenedicarboxylate (TBB)-enriched to hexylene thiophenedicarboxylate (THH)-enriched, offered significant control over crystallinity, thermal and mechanical properties. Enzymatic hydrolysis of synthetized polymers using porcine pancreatic lipase (PP-L) over a short period resulted in significant weight losses of 9.6, 11.4, 30.2, and 35 wt%, as observed by scanning electron microscopy (SEM), with perforations visible on all surfaces of the films. Thus, thiophene-based polyesters with cyclic aromatic structures similar to terephthalic acid (TPA) show great promise as PET mimics. At the same time, PP-L appears to be a promising biocatalyst for the degradation of bioplastic waste and its recycling via re-synthesis processes.

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“…This included weak asymmetric and symmetric C-H bending vibrations at 2955 and 2875 cm −1 , respectively, and a strong C=O peak attributed to the stretching vibration of ester carbonyl group attached to the phenyl ester at 1715 cm −1 . The absorption bands at 1600 and 1500 cm −1 were attributed to the disubstituted aromatic segments (C=C bond stretching) of the polymer chains [ 50 , 65 ]. A distinctive absorption peak was observed for all of the ether series at 1270 cm −1 (sp 2 ), attributed to C–O alkyl ether stretching.…”

Section: Resultsmentioning

confidence: 99%

Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols

Djouonkep

Tchameni

Selabi

et al. 2022

IJMS

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Vanillin, as a promising aromatic aldehyde, possesses worthy structural and bioactive properties useful in the design of novel sustainable polymeric materials. Its versatility and structural similarity to terephthalic acid (TPA) can lead to materials with properties similar to conventional poly(ethylene terephthalate) (PET). In this perspective, a symmetrical dimethylated dialkoxydivanillic diester monomer (DEMV) derived from vanillin was synthesized via a direct-coupling method. Then, a series of poly(ether-ester)s were synthesized via melt-polymerization incorporating mixtures of phenyl/phenyloxy diols (with hydroxyl side-chains in the 1,2-, 1,3- and 1,4-positions) and a cyclic diol, 1,4-cyclohexanedimethanol (CHDM). The polymers obtained had high molecular weights (Mw = 5.3–7.9 × 104 g.mol−1) and polydispersity index (Đ) values of 1.54–2.88. Thermal analysis showed the polymers are semi-crystalline materials with melting temperatures of 204–240 °C, and tunable glass transition temperatures (Tg) of 98–120 °C. Their 5% decomposition temperature (Td,5%) varied from 430–315 °C, which endows the polymers with a broad processing window, owing to their rigid phenyl rings and trans-CHDM groups. These poly(ether-ester)s displayed remarkable impact strength and satisfactory gas barrier properties, due to the insertion of the cyclic alkyl chain moieties. Ultimately, the synergistic influence of the ester and ether bonds provided better control over the behavior and mechanism of in vitro degradation under passive and enzymatic incubation for 90 days. Regarding the morphology, scanning electron microscopy (SEM) imaging confirmed considerable surface degradation in the polymer matrices of both polymer series, with weight losses reaching up to 35% in enzymatic degradation, which demonstrates the significant influence of ether bonds for biodegradation.

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High performance sulfur-containing copolyesters from bio-sourced aromatic monomers

Cited by 10 publications

References 42 publications

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

Synthesis of High Performance Thiophene–Aromatic Polyesters from Bio-Sourced Organic Acids and Polysaccharide-Derived Diol: Characterization and Degradability Studies

Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties

Bio-Based Degradable Poly(ether-ester)s from Melt-Polymerization of Aromatic Ester and Ether Diols

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