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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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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. |
format | Online Article Text |
id | pubmed-9965281 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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