Vinylogous urethane vitrimers

Autores
Denissen, Wim; Rivero, Guadalupe; Nicolay, Renaud; Leibler, Ludwik; Winne, Johan; Du Prez, Filip E.
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross-linked. As an alternative to the use of transesterification chemistry, we explore catalyst-free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m-xylylene diamine, and tris(2-aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress-relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation. Catalyst-free vitrimers based on the transamination of vinylogous urethanes are prepared from readily accessible chemicals. These high Tg, cross-linked materials exhibit excellent mechanical properties, while the exchangeable bonds enable full stress-relaxation on short time scales and recycling over many cycles.
Fil: Denissen, Wim. University of Ghent; Bélgica
Fil: Rivero, Guadalupe. 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: Nicolay, Renaud. University of Ghent; Bélgica
Fil: Leibler, Ludwik. University of Ghent; Bélgica
Fil: Winne, Johan. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
Materia
COVALENT ADAPTABLE NETWORKS
ENAMINONE
EXCHANGEABLE BONDS
VINYLOGOUS URETHANE
VITRIMERS
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:11336/2888
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/2888
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Vinylogous urethane vitrimersDenissen, WimRivero, GuadalupeNicolay, RenaudLeibler, LudwikWinne, JohanDu Prez, Filip E.COVALENT ADAPTABLE NETWORKSENAMINONEEXCHANGEABLE BONDSVINYLOGOUS URETHANEVITRIMERShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross-linked. As an alternative to the use of transesterification chemistry, we explore catalyst-free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m-xylylene diamine, and tris(2-aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress-relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation. Catalyst-free vitrimers based on the transamination of vinylogous urethanes are prepared from readily accessible chemicals. These high Tg, cross-linked materials exhibit excellent mechanical properties, while the exchangeable bonds enable full stress-relaxation on short time scales and recycling over many cycles.Fil: Denissen, Wim. University of Ghent; BélgicaFil: Rivero, Guadalupe. 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: Nicolay, Renaud. University of Ghent; BélgicaFil: Leibler, Ludwik. University of Ghent; BélgicaFil: Winne, Johan. University of Ghent; BélgicaFil: Du Prez, Filip E.. University of Ghent; BélgicaWiley VCH Verlag2015-03-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/2888Denissen, Wim; Rivero, Guadalupe; Nicolay, Renaud; Leibler, Ludwik; Winne, Johan; et al.; Vinylogous urethane vitrimers; Wiley VCH Verlag; Advanced Functional Materials; 25; 16; 13-3-2015; 2451-24571616-301Xenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adfm.201404553/abstract;jsessionid=F111A7D50CDD83FE2A83972F6EF0D6D0.f04t03info:eu-repo/semantics/altIdentifier/doi/10.1002/adfm.201404553info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:12:11Zoai:ri.conicet.gov.ar:11336/2888instacron: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:34982025-09-10 13:12:11.909CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vinylogous urethane vitrimers
title Vinylogous urethane vitrimers
spellingShingle Vinylogous urethane vitrimers
Denissen, Wim
COVALENT ADAPTABLE NETWORKS
ENAMINONE
EXCHANGEABLE BONDS
VINYLOGOUS URETHANE
VITRIMERS
title_short Vinylogous urethane vitrimers
title_full Vinylogous urethane vitrimers
title_fullStr Vinylogous urethane vitrimers
title_full_unstemmed Vinylogous urethane vitrimers
title_sort Vinylogous urethane vitrimers
dc.creator.none.fl_str_mv Denissen, Wim
Rivero, Guadalupe
Nicolay, Renaud
Leibler, Ludwik
Winne, Johan
Du Prez, Filip E.
author Denissen, Wim
author_facet Denissen, Wim
Rivero, Guadalupe
Nicolay, Renaud
Leibler, Ludwik
Winne, Johan
Du Prez, Filip E.
author_role author
author2 Rivero, Guadalupe
Nicolay, Renaud
Leibler, Ludwik
Winne, Johan
Du Prez, Filip E.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv COVALENT ADAPTABLE NETWORKS
ENAMINONE
EXCHANGEABLE BONDS
VINYLOGOUS URETHANE
VITRIMERS
topic COVALENT ADAPTABLE NETWORKS
ENAMINONE
EXCHANGEABLE BONDS
VINYLOGOUS URETHANE
VITRIMERS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross-linked. As an alternative to the use of transesterification chemistry, we explore catalyst-free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m-xylylene diamine, and tris(2-aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress-relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation. Catalyst-free vitrimers based on the transamination of vinylogous urethanes are prepared from readily accessible chemicals. These high Tg, cross-linked materials exhibit excellent mechanical properties, while the exchangeable bonds enable full stress-relaxation on short time scales and recycling over many cycles.
Fil: Denissen, Wim. University of Ghent; Bélgica
Fil: Rivero, Guadalupe. 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: Nicolay, Renaud. University of Ghent; Bélgica
Fil: Leibler, Ludwik. University of Ghent; Bélgica
Fil: Winne, Johan. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
description Vitrimers are a new class of polymeric materials with very attractive properties, since they can be reworked to any shape while being at the same time permanently cross-linked. As an alternative to the use of transesterification chemistry, we explore catalyst-free transamination of vinylogous urethanes as an exchange reaction for vitrimers. First, a kinetic study on model compounds reveals the occurrence of transamination of vinylogous urethanes in a good temperature window without side reactions. Next, poly(vinylogous urethane) networks with a storage modulus of ≈2.4 GPa and a glass transition temperature above 80 °C are prepared by bulk polymerization of cyclohexane dimethanol bisacetoacetate, m-xylylene diamine, and tris(2-aminoethyl)amine. The vitrimer nature of these networks is examined by solubility, stress-relaxation, and creep experiments. Relaxation times as short as 85 s at 170 °C are observed without making use of any catalyst. In addition, the networks are recyclable up to four times by consecutive grinding/compression molding cycles without significant mechanical or chemical degradation. Catalyst-free vitrimers based on the transamination of vinylogous urethanes are prepared from readily accessible chemicals. These high Tg, cross-linked materials exhibit excellent mechanical properties, while the exchangeable bonds enable full stress-relaxation on short time scales and recycling over many cycles.
publishDate 2015
dc.date.none.fl_str_mv 2015-03-13
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/11336/2888
Denissen, Wim; Rivero, Guadalupe; Nicolay, Renaud; Leibler, Ludwik; Winne, Johan; et al.; Vinylogous urethane vitrimers; Wiley VCH Verlag; Advanced Functional Materials; 25; 16; 13-3-2015; 2451-2457
1616-301X
url http://hdl.handle.net/11336/2888
identifier_str_mv Denissen, Wim; Rivero, Guadalupe; Nicolay, Renaud; Leibler, Ludwik; Winne, Johan; et al.; Vinylogous urethane vitrimers; Wiley VCH Verlag; Advanced Functional Materials; 25; 16; 13-3-2015; 2451-2457
1616-301X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adfm.201404553/abstract;jsessionid=F111A7D50CDD83FE2A83972F6EF0D6D0.f04t03
info:eu-repo/semantics/altIdentifier/doi/10.1002/adfm.201404553
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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 12.993085

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