Cargando…

Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer

The continuous search for novel biobased polymers with high-performance properties has highlighted the role of monofuranic-based polyesters as some of the most promising for future plastic industry but has neglected the huge potential for the polymers’ innovation, relatively low cost, and synthesis...

Descripción completa

Detalles Bibliográficos
Autores principales: Zaidi, Sami, Bougarech, Abdelkader, Abid, Majdi, Abid, Souhir, Silvestre, Armando J. D., Sousa, Andreia F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10222078/
https://www.ncbi.nlm.nih.gov/pubmed/37241868
http://dx.doi.org/10.3390/molecules28104124
_version_ 1785049610175119360
author Zaidi, Sami
Bougarech, Abdelkader
Abid, Majdi
Abid, Souhir
Silvestre, Armando J. D.
Sousa, Andreia F.
author_facet Zaidi, Sami
Bougarech, Abdelkader
Abid, Majdi
Abid, Souhir
Silvestre, Armando J. D.
Sousa, Andreia F.
author_sort Zaidi, Sami
collection PubMed
description The continuous search for novel biobased polymers with high-performance properties has highlighted the role of monofuranic-based polyesters as some of the most promising for future plastic industry but has neglected the huge potential for the polymers’ innovation, relatively low cost, and synthesis easiness of 5,5′-isopropylidene bis-(ethyl 2-furoate) (DEbF), obtained from the platform chemical, worldwide-produced furfural. In this vein, poly(1,12-dodecylene 5,5′-isopropylidene -bis(ethyl 2-furoate)) (PDDbF) was introduced, for the first time, as a biobased bisfuranic long-chain aliphatic polyester with an extreme flexibility function, competing with fossil-based polyethylene. This new polyester in-depth characterization confirmed its expected structure (FTIR, (1)H, and (13)C NMR) and relevant thermal features (DSC, TGA, and DMTA), notably, an essentially amorphous character with a glass transition temperature of −6 °C and main maximum decomposition temperature of 340 °C. Furthermore, PDDbF displayed an elongation at break as high as 732%, around five times higher than that of the 2,5-furandicarboxylic acid counterpart, stressing the unique features of the bisfuranic class of polymers compared to monofuranic ones. The enhanced ductility combined with the relevant thermal properties makes PDDbF a highly promising material for flexible packaging.
format Online
Article
Text
id pubmed-10222078
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-102220782023-05-28 Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer Zaidi, Sami Bougarech, Abdelkader Abid, Majdi Abid, Souhir Silvestre, Armando J. D. Sousa, Andreia F. Molecules Article The continuous search for novel biobased polymers with high-performance properties has highlighted the role of monofuranic-based polyesters as some of the most promising for future plastic industry but has neglected the huge potential for the polymers’ innovation, relatively low cost, and synthesis easiness of 5,5′-isopropylidene bis-(ethyl 2-furoate) (DEbF), obtained from the platform chemical, worldwide-produced furfural. In this vein, poly(1,12-dodecylene 5,5′-isopropylidene -bis(ethyl 2-furoate)) (PDDbF) was introduced, for the first time, as a biobased bisfuranic long-chain aliphatic polyester with an extreme flexibility function, competing with fossil-based polyethylene. This new polyester in-depth characterization confirmed its expected structure (FTIR, (1)H, and (13)C NMR) and relevant thermal features (DSC, TGA, and DMTA), notably, an essentially amorphous character with a glass transition temperature of −6 °C and main maximum decomposition temperature of 340 °C. Furthermore, PDDbF displayed an elongation at break as high as 732%, around five times higher than that of the 2,5-furandicarboxylic acid counterpart, stressing the unique features of the bisfuranic class of polymers compared to monofuranic ones. The enhanced ductility combined with the relevant thermal properties makes PDDbF a highly promising material for flexible packaging. MDPI 2023-05-16 /pmc/articles/PMC10222078/ /pubmed/37241868 http://dx.doi.org/10.3390/molecules28104124 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
Zaidi, Sami
Bougarech, Abdelkader
Abid, Majdi
Abid, Souhir
Silvestre, Armando J. D.
Sousa, Andreia F.
Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title_full Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title_fullStr Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title_full_unstemmed Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title_short Highly Flexible Poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): A Promising Biobased Polyester Derived from a Renewable Cost-Effective Bisfuranic Precursor and a Long-Chain Aliphatic Spacer
title_sort highly flexible poly(1,12-dodecylene 5,5′-isopropylidene-bis(ethyl 2-furoate)): a promising biobased polyester derived from a renewable cost-effective bisfuranic precursor and a long-chain aliphatic spacer
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10222078/
https://www.ncbi.nlm.nih.gov/pubmed/37241868
http://dx.doi.org/10.3390/molecules28104124
work_keys_str_mv AT zaidisami highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer
AT bougarechabdelkader highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer
AT abidmajdi highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer
AT abidsouhir highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer
AT silvestrearmandojd highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer
AT sousaandreiaf highlyflexiblepoly112dodecylene55isopropylidenebisethyl2furoateapromisingbiobasedpolyesterderivedfromarenewablecosteffectivebisfuranicprecursorandalongchainaliphaticspacer