Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing

Imine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate un...

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Autores: Vilanova Pérez, Anna, De la Flor López, Silvia, Fernández Francos, Xavier|||0000-0002-3492-2922, Serra Albet, Maria Àngels|||0000-0003-1387-0358, Roig Gibert, Adriá
Tipo de recurso: artículo
Fecha de publicación:2024
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:2117/405472
Acceso en línea:https://hdl.handle.net/2117/405472
https://dx.doi.org/10.1021/acsapm.3c03234
Access Level:acceso abierto
Palabra clave:Three-dimensional printing
Materials science
Chemistry, Organic
Vitrimer
Imine metathesis
3D printing
Vanillin
Methacrylate
Impressió 3D
Ciència dels materials
Química orgànica
Àrees temàtiques de la UPC::Enginyeria dels materials
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spelling Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printingVilanova Pérez, AnnaDe la Flor López, SilviaFernández Francos, Xavier|||0000-0002-3492-2922Serra Albet, Maria Àngels|||0000-0003-1387-0358Roig Gibert, AdriáThree-dimensional printingMaterials scienceChemistry, OrganicVitrimerImine metathesis3D printingVanillinMethacrylateImpressió 3DCiència dels materialsQuímica orgànicaÀrees temàtiques de la UPC::Enginyeria dels materialsImine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate units with the amine groups of hexamethylenediamine (HMDA). The synthesized product was used in formulations containing ethylene glycol phenyl ether methacrylate (EGPMA) as a reactive diluent for the customization of final material properties and cured by exposure to ultraviolet (UV)-light using suitable radical photoinitiators or else with temperature using a radical thermal initiator. Materials with glass transition temperatures (Tgs) ranging from 70 to 90 °C were prepared, showing good thermal stability and mechanical and thermomechanical properties. The evaluation of their vitrimeric characteristics revealed that all materials achieved a stress-relaxation factor (s = 0.37s0) in less than 130 s at 160 °C, with photocured materials exhibiting faster relaxation rates. The catalytic effect of phosphine oxide groups in imine metathesis has also been evidenced. All prepared materials could be mechanically recycled and completely solubilized in a two-step degradation process, putting evidence of their potential use for carbon fiber-reinforced composites (CFRCs). In addition, they demonstrated promising self-repairing abilities. Finally, as a proof of concept, it was established that these formulations could be effectively processed using a Digital Light Processing three-dimensional (3D) Printer (DLP), resulting in the fabrication of complex shapes with high resolution.This work is part of the R&D projects PID2020-115102RB- C21, PID2020-115102RB-C22, and TED2021-131102B−C22 funded by MCNI/AEI/10.13039/501100011033 and Euro- pean Union “NextGenerationEU”/PRTR. The authors ac- knowledge these grants and also thank the Generalitat de Catalunya (2021-SGR-00154).American Chemical Society (ACS)20242024-03-1420242024-03-27journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/405472https://dx.doi.org/10.1021/acsapm.3c03234reponame: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 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/4054722026-05-27T15:37:01Z
dc.title.none.fl_str_mv Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
title Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
spellingShingle Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
Vilanova Pérez, Anna
Three-dimensional printing
Materials science
Chemistry, Organic
Vitrimer
Imine metathesis
3D printing
Vanillin
Methacrylate
Impressió 3D
Ciència dels materials
Química orgànica
Àrees temàtiques de la UPC::Enginyeria dels materials
title_short Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
title_full Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
title_fullStr Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
title_full_unstemmed Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
title_sort Biobased imine vitrimers obtained by photo and thermal curing procedures-promising materials for 3D printing
dc.creator.none.fl_str_mv Vilanova Pérez, Anna
De la Flor López, Silvia
Fernández Francos, Xavier|||0000-0002-3492-2922
Serra Albet, Maria Àngels|||0000-0003-1387-0358
Roig Gibert, Adriá
author Vilanova Pérez, Anna
author_facet Vilanova Pérez, Anna
De la Flor López, Silvia
Fernández Francos, Xavier|||0000-0002-3492-2922
Serra Albet, Maria Àngels|||0000-0003-1387-0358
Roig Gibert, Adriá
author_role author
author2 De la Flor López, Silvia
Fernández Francos, Xavier|||0000-0002-3492-2922
Serra Albet, Maria Àngels|||0000-0003-1387-0358
Roig Gibert, Adriá
author2_role author
author
author
author
dc.subject.none.fl_str_mv Three-dimensional printing
Materials science
Chemistry, Organic
Vitrimer
Imine metathesis
3D printing
Vanillin
Methacrylate
Impressió 3D
Ciència dels materials
Química orgànica
Àrees temàtiques de la UPC::Enginyeria dels materials
topic Three-dimensional printing
Materials science
Chemistry, Organic
Vitrimer
Imine metathesis
3D printing
Vanillin
Methacrylate
Impressió 3D
Ciència dels materials
Química orgànica
Àrees temàtiques de la UPC::Enginyeria dels materials
description Imine-based vitrimers were prepared from synthesized diimine-dimethacrylate monomer derived from biobased vanillin. First, a methacrylate derivative starting from vanillin was synthesized. The diimine derivative was synthesized by condensation of the aldehyde groups from two vanillin methacrylate units with the amine groups of hexamethylenediamine (HMDA). The synthesized product was used in formulations containing ethylene glycol phenyl ether methacrylate (EGPMA) as a reactive diluent for the customization of final material properties and cured by exposure to ultraviolet (UV)-light using suitable radical photoinitiators or else with temperature using a radical thermal initiator. Materials with glass transition temperatures (Tgs) ranging from 70 to 90 °C were prepared, showing good thermal stability and mechanical and thermomechanical properties. The evaluation of their vitrimeric characteristics revealed that all materials achieved a stress-relaxation factor (s = 0.37s0) in less than 130 s at 160 °C, with photocured materials exhibiting faster relaxation rates. The catalytic effect of phosphine oxide groups in imine metathesis has also been evidenced. All prepared materials could be mechanically recycled and completely solubilized in a two-step degradation process, putting evidence of their potential use for carbon fiber-reinforced composites (CFRCs). In addition, they demonstrated promising self-repairing abilities. Finally, as a proof of concept, it was established that these formulations could be effectively processed using a Digital Light Processing three-dimensional (3D) Printer (DLP), resulting in the fabrication of complex shapes with high resolution.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024-03-14
2024
2024-03-27
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/2117/405472
https://dx.doi.org/10.1021/acsapm.3c03234
url https://hdl.handle.net/2117/405472
https://dx.doi.org/10.1021/acsapm.3c03234
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 4.0 International
http://creativecommons.org/licenses/by/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 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
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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