Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains

Autores
Altuna, Facundo Ignacio; Casado, Ulises Martín; Dell'Erba, Ignacio Esteban; Luna, L.; Hoppe, Cristina Elena; Williams, Roberto Juan Jose
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Epoxy vitrimers were synthesized employing stoichiometric amounts of diglycidyl ether of bisphenol A (DGEBA), sebacic acid (20% eq.) and an n-alkylamine, either octylamine (OA), dodecylamine (DA) or hexadecylamine (HA) (80% eq.). Apart from the chemical crosslinks generated by diester groups formed in transesterification reactions, these vitrimers include physical crosslinks arising from self-association of alkyl chains. The relative fraction and strength of physical crosslinks was high for octylamine (OA), intermediate for dodecylamine (DA) and low for hexadecylamine (HA). This was reflected by rubbery moduli that increased significantly from HA to OA. The covalently bonded tertiary amine generated in the epoxy-amine addition reaction was an efficient catalyst of transesterification reactions. Relatively fast stress relaxation rates were observed driven by transesterification reactions coupled to the dynamic exchange of self-associated alkyl chains. The occurrence of this last mechanism was evidenced by the stress relaxation observed for the linear polymer synthesized with stoichiometric amounts of DGEBA and OA that forms a permanent network up to temperatures close to degradation due to the presence of a high fraction of self-associated n-octyl chains. These vitrimers might find applications in several fields such as soft robotics, electro and magnetorheological elastomers, soft tissues and in additive manufacturing.
Fil: Altuna, Facundo Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Casado, Ulises Martín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Dell'Erba, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Luna, L.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Hoppe, Cristina Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Williams, Roberto Juan Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Materia
Vitrimers
Epoxy
Alkyl chains
Physical crosslinks
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/132058
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chainsAltuna, Facundo IgnacioCasado, Ulises MartínDell'Erba, Ignacio EstebanLuna, L.Hoppe, Cristina ElenaWilliams, Roberto Juan JoseVitrimersEpoxyAlkyl chainsPhysical crosslinkshttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2Epoxy vitrimers were synthesized employing stoichiometric amounts of diglycidyl ether of bisphenol A (DGEBA), sebacic acid (20% eq.) and an n-alkylamine, either octylamine (OA), dodecylamine (DA) or hexadecylamine (HA) (80% eq.). Apart from the chemical crosslinks generated by diester groups formed in transesterification reactions, these vitrimers include physical crosslinks arising from self-association of alkyl chains. The relative fraction and strength of physical crosslinks was high for octylamine (OA), intermediate for dodecylamine (DA) and low for hexadecylamine (HA). This was reflected by rubbery moduli that increased significantly from HA to OA. The covalently bonded tertiary amine generated in the epoxy-amine addition reaction was an efficient catalyst of transesterification reactions. Relatively fast stress relaxation rates were observed driven by transesterification reactions coupled to the dynamic exchange of self-associated alkyl chains. The occurrence of this last mechanism was evidenced by the stress relaxation observed for the linear polymer synthesized with stoichiometric amounts of DGEBA and OA that forms a permanent network up to temperatures close to degradation due to the presence of a high fraction of self-associated n-octyl chains. These vitrimers might find applications in several fields such as soft robotics, electro and magnetorheological elastomers, soft tissues and in additive manufacturing.Fil: Altuna, Facundo Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaFil: Casado, Ulises Martín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaFil: Dell'Erba, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaFil: Luna, L.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaFil: Hoppe, Cristina Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaFil: Williams, Roberto Juan Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; ArgentinaRoyal Society of Chemistry2020-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/132058Altuna, Facundo Ignacio; Casado, Ulises Martín; Dell'Erba, Ignacio Esteban; Luna, L.; Hoppe, Cristina Elena; et al.; Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains; Royal Society of Chemistry; Polymer Chemistry; 11; 7; 2-2020; 1337-13471759-9962CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9PY01787Ainfo:eu-repo/semantics/altIdentifier/doi/10.1039/C9PY01787Ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:03:38Zoai:ri.conicet.gov.ar:11336/132058instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:03:39.027CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
title Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
spellingShingle Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
Altuna, Facundo Ignacio
Vitrimers
Epoxy
Alkyl chains
Physical crosslinks
title_short Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
title_full Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
title_fullStr Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
title_full_unstemmed Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
title_sort Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains
dc.creator.none.fl_str_mv Altuna, Facundo Ignacio
Casado, Ulises Martín
Dell'Erba, Ignacio Esteban
Luna, L.
Hoppe, Cristina Elena
Williams, Roberto Juan Jose
author Altuna, Facundo Ignacio
author_facet Altuna, Facundo Ignacio
Casado, Ulises Martín
Dell'Erba, Ignacio Esteban
Luna, L.
Hoppe, Cristina Elena
Williams, Roberto Juan Jose
author_role author
author2 Casado, Ulises Martín
Dell'Erba, Ignacio Esteban
Luna, L.
Hoppe, Cristina Elena
Williams, Roberto Juan Jose
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Vitrimers
Epoxy
Alkyl chains
Physical crosslinks
topic Vitrimers
Epoxy
Alkyl chains
Physical crosslinks
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Epoxy vitrimers were synthesized employing stoichiometric amounts of diglycidyl ether of bisphenol A (DGEBA), sebacic acid (20% eq.) and an n-alkylamine, either octylamine (OA), dodecylamine (DA) or hexadecylamine (HA) (80% eq.). Apart from the chemical crosslinks generated by diester groups formed in transesterification reactions, these vitrimers include physical crosslinks arising from self-association of alkyl chains. The relative fraction and strength of physical crosslinks was high for octylamine (OA), intermediate for dodecylamine (DA) and low for hexadecylamine (HA). This was reflected by rubbery moduli that increased significantly from HA to OA. The covalently bonded tertiary amine generated in the epoxy-amine addition reaction was an efficient catalyst of transesterification reactions. Relatively fast stress relaxation rates were observed driven by transesterification reactions coupled to the dynamic exchange of self-associated alkyl chains. The occurrence of this last mechanism was evidenced by the stress relaxation observed for the linear polymer synthesized with stoichiometric amounts of DGEBA and OA that forms a permanent network up to temperatures close to degradation due to the presence of a high fraction of self-associated n-octyl chains. These vitrimers might find applications in several fields such as soft robotics, electro and magnetorheological elastomers, soft tissues and in additive manufacturing.
Fil: Altuna, Facundo Ignacio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Casado, Ulises Martín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Dell'Erba, Ignacio Esteban. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Luna, L.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Hoppe, Cristina Elena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
Fil: Williams, Roberto Juan Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata. Instituto de Investigaciones en Ciencia y Tecnología de Materiales. Universidad Nacional de Mar del Plata. Facultad de Ingeniería. Instituto de Investigaciones en Ciencia y Tecnología de Materiales; Argentina
description Epoxy vitrimers were synthesized employing stoichiometric amounts of diglycidyl ether of bisphenol A (DGEBA), sebacic acid (20% eq.) and an n-alkylamine, either octylamine (OA), dodecylamine (DA) or hexadecylamine (HA) (80% eq.). Apart from the chemical crosslinks generated by diester groups formed in transesterification reactions, these vitrimers include physical crosslinks arising from self-association of alkyl chains. The relative fraction and strength of physical crosslinks was high for octylamine (OA), intermediate for dodecylamine (DA) and low for hexadecylamine (HA). This was reflected by rubbery moduli that increased significantly from HA to OA. The covalently bonded tertiary amine generated in the epoxy-amine addition reaction was an efficient catalyst of transesterification reactions. Relatively fast stress relaxation rates were observed driven by transesterification reactions coupled to the dynamic exchange of self-associated alkyl chains. The occurrence of this last mechanism was evidenced by the stress relaxation observed for the linear polymer synthesized with stoichiometric amounts of DGEBA and OA that forms a permanent network up to temperatures close to degradation due to the presence of a high fraction of self-associated n-octyl chains. These vitrimers might find applications in several fields such as soft robotics, electro and magnetorheological elastomers, soft tissues and in additive manufacturing.
publishDate 2020
dc.date.none.fl_str_mv 2020-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/132058
Altuna, Facundo Ignacio; Casado, Ulises Martín; Dell'Erba, Ignacio Esteban; Luna, L.; Hoppe, Cristina Elena; et al.; Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains; Royal Society of Chemistry; Polymer Chemistry; 11; 7; 2-2020; 1337-1347
1759-9962
CONICET Digital
CONICET
url http://hdl.handle.net/11336/132058
identifier_str_mv Altuna, Facundo Ignacio; Casado, Ulises Martín; Dell'Erba, Ignacio Esteban; Luna, L.; Hoppe, Cristina Elena; et al.; Epoxy vitrimers incorporating physical crosslinks produced by self-association of alkyl chains; Royal Society of Chemistry; Polymer Chemistry; 11; 7; 2-2020; 1337-1347
1759-9962
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9PY01787A
info:eu-repo/semantics/altIdentifier/doi/10.1039/C9PY01787A
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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