Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials

A series of poly(thiourethanes) (PTUs) from biobased monomers have been synthesized. Limonene and squalene were transformed into polyfunctional thiols by thiol-ene reaction with thioacetic acid and further saponification. They were then reacted in different proportions with hexamethylene diisocyanat...

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Autores: Guerrero Ruiz, Federico, Ramis Juan, Xavier|||0000-0003-2550-7185, De la Flor López, Silvia, Serra Albet, Maria Àngels|||0000-0003-1387-0358
Tipo de recurso: artículo
Fecha de publicación:2023
País:España
Institución:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/386733
Acceso en línea:https://hdl.handle.net/2117/386733
https://dx.doi.org/10.3390/polym15061583
Access Level:acceso abierto
Palabra clave:Polymers
Poly(thiourethanes)
Thiol
Vitrimers
Renewable
Bio-based monomers
Polímers
Àrees temàtiques de la UPC::Física
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spelling Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like MaterialsGuerrero Ruiz, FedericoRamis Juan, Xavier|||0000-0003-2550-7185De la Flor López, SilviaSerra Albet, Maria Àngels|||0000-0003-1387-0358PolymersPoly(thiourethanes)ThiolVitrimersRenewableBio-based monomersPolímersÀrees temàtiques de la UPC::FísicaA series of poly(thiourethanes) (PTUs) from biobased monomers have been synthesized. Limonene and squalene were transformed into polyfunctional thiols by thiol-ene reaction with thioacetic acid and further saponification. They were then reacted in different proportions with hexamethylene diisocyanate (HDI) in the presence of a catalyst to prepare bio-based poly(thiourethane) vitrimer-like materials. The different functionalities of squalene and limonene thiols (six and two, respectively) allow for changing the characteristics of the final material by only varying their relative proportions in the reactive mixture. The proportions of thiol and isocyanate groups were stoichiometric in all the formulations tested. An acidic and a basic catalyst were tested in the preparation of the networked polymers. As the acidic catalyst, we selected dibutyltin dilaurate (DBTDL), and as the basic catalyst, a tetraphenylborate salt of 1,8-diazabicyclo(5.4.0)undec-7-ene (BGDBU), which has the advantage of only releasing the base at high temperatures. The materials obtained were characterized by thermogravimetry and thermomechanical analysis. The vitrimeric-like behavior was evaluated, and we could see that higher proportions of the limonene derivative in the formulations led to faster stress relaxation of the material. The use of the base catalyst led to a much shorter relaxation time. The materials obtained demonstrated good self-healing efficiencyPeer ReviewedMultidisciplinary Digital Publishing Institute (MDPI)20232023-03-0120232023-04-26journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/386733https://dx.doi.org/10.3390/polym15061583reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/3867332026-05-27T15:37:01Z
dc.title.none.fl_str_mv Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
title Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
spellingShingle Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
Guerrero Ruiz, Federico
Polymers
Poly(thiourethanes)
Thiol
Vitrimers
Renewable
Bio-based monomers
Polímers
Àrees temàtiques de la UPC::Física
title_short Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
title_full Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
title_fullStr Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
title_full_unstemmed Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
title_sort Preparation and Characterization of a Series of Self-Healable Bio-Based Poly(thiourethane) Vitrimer-like Materials
dc.creator.none.fl_str_mv Guerrero Ruiz, Federico
Ramis Juan, Xavier|||0000-0003-2550-7185
De la Flor López, Silvia
Serra Albet, Maria Àngels|||0000-0003-1387-0358
author Guerrero Ruiz, Federico
author_facet Guerrero Ruiz, Federico
Ramis Juan, Xavier|||0000-0003-2550-7185
De la Flor López, Silvia
Serra Albet, Maria Àngels|||0000-0003-1387-0358
author_role author
author2 Ramis Juan, Xavier|||0000-0003-2550-7185
De la Flor López, Silvia
Serra Albet, Maria Àngels|||0000-0003-1387-0358
author2_role author
author
author
dc.subject.none.fl_str_mv Polymers
Poly(thiourethanes)
Thiol
Vitrimers
Renewable
Bio-based monomers
Polímers
Àrees temàtiques de la UPC::Física
topic Polymers
Poly(thiourethanes)
Thiol
Vitrimers
Renewable
Bio-based monomers
Polímers
Àrees temàtiques de la UPC::Física
description A series of poly(thiourethanes) (PTUs) from biobased monomers have been synthesized. Limonene and squalene were transformed into polyfunctional thiols by thiol-ene reaction with thioacetic acid and further saponification. They were then reacted in different proportions with hexamethylene diisocyanate (HDI) in the presence of a catalyst to prepare bio-based poly(thiourethane) vitrimer-like materials. The different functionalities of squalene and limonene thiols (six and two, respectively) allow for changing the characteristics of the final material by only varying their relative proportions in the reactive mixture. The proportions of thiol and isocyanate groups were stoichiometric in all the formulations tested. An acidic and a basic catalyst were tested in the preparation of the networked polymers. As the acidic catalyst, we selected dibutyltin dilaurate (DBTDL), and as the basic catalyst, a tetraphenylborate salt of 1,8-diazabicyclo(5.4.0)undec-7-ene (BGDBU), which has the advantage of only releasing the base at high temperatures. The materials obtained were characterized by thermogravimetry and thermomechanical analysis. The vitrimeric-like behavior was evaluated, and we could see that higher proportions of the limonene derivative in the formulations led to faster stress relaxation of the material. The use of the base catalyst led to a much shorter relaxation time. The materials obtained demonstrated good self-healing efficiency
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-03-01
2023
2023-04-26
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/2117/386733
https://dx.doi.org/10.3390/polym15061583
url https://hdl.handle.net/2117/386733
https://dx.doi.org/10.3390/polym15061583
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute (MDPI)
dc.source.none.fl_str_mv reponame:UPCommons. Portal del coneixement obert de la UPC
instname:Universitat Politècnica de Catalunya (UPC)
instname_str Universitat Politècnica de Catalunya (UPC)
reponame_str UPCommons. Portal del coneixement obert de la UPC
collection UPCommons. Portal del coneixement obert de la UPC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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