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

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 me...

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Autores principales: Djouonkep, Lesly Dasilva Wandji, Tamo, Christian Tatchum, Simo, Belle Elda, Issah, Nasiru, Tchouagtie, Marc Nivic, Selabi, Naomie Beolle Songwe, Doench, Ingo, Kamdem Tamo, Arnaud, Xie, Binqiang, Osorio-Madrazo, Anayancy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9965281/
https://www.ncbi.nlm.nih.gov/pubmed/36838821
http://dx.doi.org/10.3390/molecules28041825
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author Djouonkep, Lesly Dasilva Wandji
Tamo, Christian Tatchum
Simo, Belle Elda
Issah, Nasiru
Tchouagtie, Marc Nivic
Selabi, Naomie Beolle Songwe
Doench, Ingo
Kamdem Tamo, Arnaud
Xie, Binqiang
Osorio-Madrazo, Anayancy
author_facet Djouonkep, Lesly Dasilva Wandji
Tamo, Christian Tatchum
Simo, Belle Elda
Issah, Nasiru
Tchouagtie, Marc Nivic
Selabi, Naomie Beolle Songwe
Doench, Ingo
Kamdem Tamo, Arnaud
Xie, Binqiang
Osorio-Madrazo, Anayancy
author_sort Djouonkep, Lesly Dasilva Wandji
collection PubMed
description 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) (PTB(x)H(y)) were conducted via a controlled melt polymerization method. Fourier-transform infrared (FTIR) and nuclear magnetic resonance ((1)H 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 × 10(3) g/mol. The glass transition temperature (T(g)) 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 polyethylene terephthalate. 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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spelling pubmed-99652812023-02-26 Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties Djouonkep, Lesly Dasilva Wandji Tamo, Christian Tatchum Simo, Belle Elda Issah, Nasiru Tchouagtie, Marc Nivic Selabi, Naomie Beolle Songwe Doench, Ingo Kamdem Tamo, Arnaud Xie, Binqiang Osorio-Madrazo, Anayancy Molecules Article 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) (PTB(x)H(y)) were conducted via a controlled melt polymerization method. Fourier-transform infrared (FTIR) and nuclear magnetic resonance ((1)H 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 × 10(3) g/mol. The glass transition temperature (T(g)) 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 polyethylene terephthalate. 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. MDPI 2023-02-15 /pmc/articles/PMC9965281/ /pubmed/36838821 http://dx.doi.org/10.3390/molecules28041825 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Djouonkep, Lesly Dasilva Wandji
Tamo, Christian Tatchum
Simo, Belle Elda
Issah, Nasiru
Tchouagtie, Marc Nivic
Selabi, Naomie Beolle Songwe
Doench, Ingo
Kamdem Tamo, Arnaud
Xie, Binqiang
Osorio-Madrazo, Anayancy
Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title_full Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title_fullStr Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title_full_unstemmed Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title_short Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties
title_sort synthesis by melt-polymerization of a novel series of bio-based and biodegradable thiophene-containing copolyesters with promising gas barrier and high thermomechanical properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9965281/
https://www.ncbi.nlm.nih.gov/pubmed/36838821
http://dx.doi.org/10.3390/molecules28041825
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