Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links

Autores
Wolfel Sánchez, Alexis; Alvarez Igarzabal, Cecilia Ines; Romero, Marcelo Ricardo
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The development of new materials with smart properties is currently expanding the development of new technologies. Therefore, the design of materials with novel sensitivities and smart behavior is important for the development of smart systems with automated responsivity. We have recently reported the synthesis of hydrogels, cross-linked by N,N´-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating changes in the hydrogel properties, as well as generating valuable α-oxo-aldehyde functional groups useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from 2-aminoethyl methacrylate hydrochloride (AEMA), coexisting with DAT into the same network. Herein, α-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.
Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Materia
DIOL
IMINE
N,N'-DIALLYLTARTARDIAMIDE
PERIODATE
SELF-HEALING
Α-OXOALDEHYDE
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:11336/143554
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/143554
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-linksWolfel Sánchez, AlexisAlvarez Igarzabal, Cecilia InesRomero, Marcelo RicardoDIOLIMINEN,N'-DIALLYLTARTARDIAMIDEPERIODATESELF-HEALINGΑ-OXOALDEHYDEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The development of new materials with smart properties is currently expanding the development of new technologies. Therefore, the design of materials with novel sensitivities and smart behavior is important for the development of smart systems with automated responsivity. We have recently reported the synthesis of hydrogels, cross-linked by N,N´-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating changes in the hydrogel properties, as well as generating valuable α-oxo-aldehyde functional groups useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from 2-aminoethyl methacrylate hydrochloride (AEMA), coexisting with DAT into the same network. Herein, α-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaFil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaFil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; ArgentinaPergamon-Elsevier Science Ltd2020-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143554Wolfel Sánchez, Alexis; Alvarez Igarzabal, Cecilia Ines; Romero, Marcelo Ricardo; Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links; Pergamon-Elsevier Science Ltd; European Polymer Journal; 140; 11-2020; 1-100014-3057CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0014305720317523info:eu-repo/semantics/altIdentifier/doi/10.1016/j.eurpolymj.2020.110038info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-05T10:46:40Zoai:ri.conicet.gov.ar:11336/143554instacron: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:34982025-11-05 10:46:40.998CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
title Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
spellingShingle Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
Wolfel Sánchez, Alexis
DIOL
IMINE
N,N'-DIALLYLTARTARDIAMIDE
PERIODATE
SELF-HEALING
Α-OXOALDEHYDE
title_short Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
title_full Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
title_fullStr Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
title_full_unstemmed Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
title_sort Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links
dc.creator.none.fl_str_mv Wolfel Sánchez, Alexis
Alvarez Igarzabal, Cecilia Ines
Romero, Marcelo Ricardo
author Wolfel Sánchez, Alexis
author_facet Wolfel Sánchez, Alexis
Alvarez Igarzabal, Cecilia Ines
Romero, Marcelo Ricardo
author_role author
author2 Alvarez Igarzabal, Cecilia Ines
Romero, Marcelo Ricardo
author2_role author
author
dc.subject.none.fl_str_mv DIOL
IMINE
N,N'-DIALLYLTARTARDIAMIDE
PERIODATE
SELF-HEALING
Α-OXOALDEHYDE
topic DIOL
IMINE
N,N'-DIALLYLTARTARDIAMIDE
PERIODATE
SELF-HEALING
Α-OXOALDEHYDE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The development of new materials with smart properties is currently expanding the development of new technologies. Therefore, the design of materials with novel sensitivities and smart behavior is important for the development of smart systems with automated responsivity. We have recently reported the synthesis of hydrogels, cross-linked by N,N´-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating changes in the hydrogel properties, as well as generating valuable α-oxo-aldehyde functional groups useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from 2-aminoethyl methacrylate hydrochloride (AEMA), coexisting with DAT into the same network. Herein, α-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.
Fil: Wolfel Sánchez, Alexis. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Alvarez Igarzabal, Cecilia Ines. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
Fil: Romero, Marcelo Ricardo. Universidad Nacional de Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigación y Desarrollo en Ingeniería de Procesos y Química Aplicada; Argentina
description The development of new materials with smart properties is currently expanding the development of new technologies. Therefore, the design of materials with novel sensitivities and smart behavior is important for the development of smart systems with automated responsivity. We have recently reported the synthesis of hydrogels, cross-linked by N,N´-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating changes in the hydrogel properties, as well as generating valuable α-oxo-aldehyde functional groups useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from 2-aminoethyl methacrylate hydrochloride (AEMA), coexisting with DAT into the same network. Herein, α-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.
publishDate 2020
dc.date.none.fl_str_mv 2020-11
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/11336/143554
Wolfel Sánchez, Alexis; Alvarez Igarzabal, Cecilia Ines; Romero, Marcelo Ricardo; Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links; Pergamon-Elsevier Science Ltd; European Polymer Journal; 140; 11-2020; 1-10
0014-3057
CONICET Digital
CONICET
url http://hdl.handle.net/11336/143554
identifier_str_mv Wolfel Sánchez, Alexis; Alvarez Igarzabal, Cecilia Ines; Romero, Marcelo Ricardo; Imine bonding self-repair hydrogels after periodate-triggered breakage of their cross-links; Pergamon-Elsevier Science Ltd; European Polymer Journal; 140; 11-2020; 1-10
0014-3057
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://linkinghub.elsevier.com/retrieve/pii/S0014305720317523
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.eurpolymj.2020.110038
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
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.084122

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