Dual-cured thermosets based on eugenol derivatives and thiol chemistry

This paper aims to increase sustainability in thermosetting polymeric fields using bio-based monomers and environmentally friendly processing technologies based on dual-curing. Eugenol has been transformed into acrylate epoxy eugenol (AEEU) that can participate in thio-Michael additions and thiol-ep...

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Detalhes bibliográficos
Autores: Roig Gibert, Adriá, Ramis Juan, Xavier|||0000-0003-2550-7185, De la Flor López, Silvia, Serra Albet, Maria Àngels|||0000-0003-1387-0358
Formato: artículo
Fecha de publicación:2023
País:España
Recursos:Universitat Politècnica de Catalunya (UPC)
Repositorio:UPCommons. Portal del coneixement obert de la UPC
Idioma:inglés
OAI Identifier:oai:upcommons.upc.edu:2117/397927
Acesso em linha:https://hdl.handle.net/2117/397927
https://dx.doi.org/10.1016/j.eurpolymj.2023.112499
Access Level:acceso abierto
Palavra-chave:Polymers--Thermal properties
Catalysis
Thiols
Biobased
Eugenol
Dual-curing
Thio-Michael
Thermosets
Polímers--Propietats tèrmiques
Catàlisi
Tiols
Àrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímers
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spelling Dual-cured thermosets based on eugenol derivatives and thiol chemistryRoig Gibert, AdriáRamis Juan, Xavier|||0000-0003-2550-7185De la Flor López, SilviaSerra Albet, Maria Àngels|||0000-0003-1387-0358Polymers--Thermal propertiesCatalysisThiolsBiobasedEugenolDual-curingThio-MichaelThermosetsPolímers--Propietats tèrmiquesCatàlisiTiolsÀrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímersThis paper aims to increase sustainability in thermosetting polymeric fields using bio-based monomers and environmentally friendly processing technologies based on dual-curing. Eugenol has been transformed into acrylate epoxy eugenol (AEEU) that can participate in thio-Michael additions and thiol-epoxy reactions. These reactions constitute the first and second steps of the sequential dual-curing process. A basic catalyst has been added to favor the kinetics of the curing process. We have selected three thiols with functionalities 3, 4, and 6, the first is derived from eugenol, and the others are derived from pentaerythritol, all can be obtained from renewable resources. To tailor and improve the intermediate material characteristics in the dual-curing process, we have added the triacrylate of glycerol. By changing its proportion, a liquid or a rubbery solid can be obtained as an intermediate, which allows a significant number of application technologies. Rheology, DSC, and FTIR were used to follow the evolution of both curing steps and to confirm the sequential character of the dual-curing. The thermal characteristics of intermediate and final materials have been evaluated by TGA and DMTA. Tensile tests at break were performed to evaluate the mechanical properties.This work is part of the R&D projects PID2020-115102RB-C21 and PID2020-115102RB-C22 funded by MCNI/AEI/10.13039/501100011033 and European Union “NextGenerationEU”/PRTR. We acknowledge these grants, and we also thank the Generalitat de Catalunya (2021-SGR00154). Bruno Bock Thiochemicals is acknowledge for kindly giving us thiol monomers.Elsevier20232023-11-2220232023-12-13journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/397927https://dx.doi.org/10.1016/j.eurpolymj.2023.112499reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)InglésengAgencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-115102RB-C21 PROCESADO DUAL DE VITRIMEROS: MATERIALES SOSTENIBLESAgencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-115102RB-C22 PROCESADO DUAL DE VITRIMEROS: IMPRESION 3Dopen 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:2117/3979272026-05-27T15:37:01Z
dc.title.none.fl_str_mv Dual-cured thermosets based on eugenol derivatives and thiol chemistry
title Dual-cured thermosets based on eugenol derivatives and thiol chemistry
spellingShingle Dual-cured thermosets based on eugenol derivatives and thiol chemistry
Roig Gibert, Adriá
Polymers--Thermal properties
Catalysis
Thiols
Biobased
Eugenol
Dual-curing
Thio-Michael
Thermosets
Polímers--Propietats tèrmiques
Catàlisi
Tiols
Àrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímers
title_short Dual-cured thermosets based on eugenol derivatives and thiol chemistry
title_full Dual-cured thermosets based on eugenol derivatives and thiol chemistry
title_fullStr Dual-cured thermosets based on eugenol derivatives and thiol chemistry
title_full_unstemmed Dual-cured thermosets based on eugenol derivatives and thiol chemistry
title_sort Dual-cured thermosets based on eugenol derivatives and thiol chemistry
dc.creator.none.fl_str_mv Roig Gibert, Adriá
Ramis Juan, Xavier|||0000-0003-2550-7185
De la Flor López, Silvia
Serra Albet, Maria Àngels|||0000-0003-1387-0358
author Roig Gibert, Adriá
author_facet Roig Gibert, Adriá
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--Thermal properties
Catalysis
Thiols
Biobased
Eugenol
Dual-curing
Thio-Michael
Thermosets
Polímers--Propietats tèrmiques
Catàlisi
Tiols
Àrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímers
topic Polymers--Thermal properties
Catalysis
Thiols
Biobased
Eugenol
Dual-curing
Thio-Michael
Thermosets
Polímers--Propietats tèrmiques
Catàlisi
Tiols
Àrees temàtiques de la UPC::Enginyeria dels materials::Materials plàstics i polímers
description This paper aims to increase sustainability in thermosetting polymeric fields using bio-based monomers and environmentally friendly processing technologies based on dual-curing. Eugenol has been transformed into acrylate epoxy eugenol (AEEU) that can participate in thio-Michael additions and thiol-epoxy reactions. These reactions constitute the first and second steps of the sequential dual-curing process. A basic catalyst has been added to favor the kinetics of the curing process. We have selected three thiols with functionalities 3, 4, and 6, the first is derived from eugenol, and the others are derived from pentaerythritol, all can be obtained from renewable resources. To tailor and improve the intermediate material characteristics in the dual-curing process, we have added the triacrylate of glycerol. By changing its proportion, a liquid or a rubbery solid can be obtained as an intermediate, which allows a significant number of application technologies. Rheology, DSC, and FTIR were used to follow the evolution of both curing steps and to confirm the sequential character of the dual-curing. The thermal characteristics of intermediate and final materials have been evaluated by TGA and DMTA. Tensile tests at break were performed to evaluate the mechanical properties.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023-11-22
2023
2023-12-13
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/2117/397927
https://dx.doi.org/10.1016/j.eurpolymj.2023.112499
url https://hdl.handle.net/2117/397927
https://dx.doi.org/10.1016/j.eurpolymj.2023.112499
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-115102RB-C21 PROCESADO DUAL DE VITRIMEROS: MATERIALES SOSTENIBLES
Agencia Estatal de Investigación http://doi.org/10.13039/501100011033 Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020 PID2020-115102RB-C22 PROCESADO DUAL DE VITRIMEROS: IMPRESION 3D
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 Elsevier
publisher.none.fl_str_mv Elsevier
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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