Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks

Autores
Hoppe, Cristina Elena; Galante, Maria Jose; Oyanguren, Patricia Angelica; Williams, Roberto Juan Jose
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Reactions taking place in a homogeneous solution of an epoxy monomer based on the diglycidyl ether of bisphenol A (DGEBA) and palmitic acid (PA), in the presence of benzyldimethylamine (BDMA), were investigated using Fourier‐transformed infrared spectroscopy (FTIR) and size exclusion chromatography (SEC). In the stoichiometric formulations prepared with equal molar ratios of epoxy (E) to carboxyl groups, E/PA = 1, the main reaction was the carboxyl addition to the epoxy giving a β‐hydroxy ester. This reaction was followed by transesterification that occurred to a very small extent. In the formulations prepared with an epoxy excess, E/PA > 1, the transesterification reactions were very significant as well as the homopolymerization of the epoxy excess that took place to an almost complete conversion. Reaction products synthesized in the range of 1 < E/PA < 2 were solids at room temperature due to the crystallization of a fraction of fatty acid chains. Above the melting temperature, reaction products recovered the liquid state. The formulation synthesized with E/PA = 2 exhibited a good behavior as a hot‐melt adhesive of steel sheets with a single lap‐shear strength of 2.5 MPa and an interfacial‐cohesive failure. For E/PA > 3, the gelation took place leading to the networks exhibiting a single glass transition temperature (Tg) without any evidence of crystallization or phase separation. Tg varied from 90 °C for the neat epoxy to 0 °C for the formulation with E/PA = 3.
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: Galante, Maria 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
Fil: Oyanguren, Patricia Angelica. 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
EPOXY
HOT-MELT ADHESIVES
PALMITIC ACID
PLASTICIZATION
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:11336/94725
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/94725
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networksHoppe, Cristina ElenaGalante, Maria JoseOyanguren, Patricia AngelicaWilliams, Roberto Juan JoseEPOXYHOT-MELT ADHESIVESPALMITIC ACIDPLASTICIZATIONhttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2Reactions taking place in a homogeneous solution of an epoxy monomer based on the diglycidyl ether of bisphenol A (DGEBA) and palmitic acid (PA), in the presence of benzyldimethylamine (BDMA), were investigated using Fourier‐transformed infrared spectroscopy (FTIR) and size exclusion chromatography (SEC). In the stoichiometric formulations prepared with equal molar ratios of epoxy (E) to carboxyl groups, E/PA = 1, the main reaction was the carboxyl addition to the epoxy giving a β‐hydroxy ester. This reaction was followed by transesterification that occurred to a very small extent. In the formulations prepared with an epoxy excess, E/PA > 1, the transesterification reactions were very significant as well as the homopolymerization of the epoxy excess that took place to an almost complete conversion. Reaction products synthesized in the range of 1 < E/PA < 2 were solids at room temperature due to the crystallization of a fraction of fatty acid chains. Above the melting temperature, reaction products recovered the liquid state. The formulation synthesized with E/PA = 2 exhibited a good behavior as a hot‐melt adhesive of steel sheets with a single lap‐shear strength of 2.5 MPa and an interfacial‐cohesive failure. For E/PA > 3, the gelation took place leading to the networks exhibiting a single glass transition temperature (Tg) without any evidence of crystallization or phase separation. Tg varied from 90 °C for the neat epoxy to 0 °C for the formulation with E/PA = 3.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; ArgentinaFil: Galante, Maria 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; ArgentinaFil: Oyanguren, Patricia Angelica. 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; ArgentinaWiley VCH Verlag2005-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/94725Hoppe, Cristina Elena; Galante, Maria Jose; Oyanguren, Patricia Angelica; Williams, Roberto Juan Jose; Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks; Wiley VCH Verlag; Macromolecular Materials and Engineering (print); 290; 5; 5-2005; 456-4621438-7492CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/mame.200400348info:eu-repo/semantics/altIdentifier/doi/10.1002/mame.200400348info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:57:02Zoai:ri.conicet.gov.ar:11336/94725instacron: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:34982025-09-29 09:57:02.336CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
title Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
spellingShingle Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
Hoppe, Cristina Elena
EPOXY
HOT-MELT ADHESIVES
PALMITIC ACID
PLASTICIZATION
title_short Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
title_full Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
title_fullStr Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
title_full_unstemmed Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
title_sort Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks
dc.creator.none.fl_str_mv Hoppe, Cristina Elena
Galante, Maria Jose
Oyanguren, Patricia Angelica
Williams, Roberto Juan Jose
author Hoppe, Cristina Elena
author_facet Hoppe, Cristina Elena
Galante, Maria Jose
Oyanguren, Patricia Angelica
Williams, Roberto Juan Jose
author_role author
author2 Galante, Maria Jose
Oyanguren, Patricia Angelica
Williams, Roberto Juan Jose
author2_role author
author
author
dc.subject.none.fl_str_mv EPOXY
HOT-MELT ADHESIVES
PALMITIC ACID
PLASTICIZATION
topic EPOXY
HOT-MELT ADHESIVES
PALMITIC ACID
PLASTICIZATION
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv Reactions taking place in a homogeneous solution of an epoxy monomer based on the diglycidyl ether of bisphenol A (DGEBA) and palmitic acid (PA), in the presence of benzyldimethylamine (BDMA), were investigated using Fourier‐transformed infrared spectroscopy (FTIR) and size exclusion chromatography (SEC). In the stoichiometric formulations prepared with equal molar ratios of epoxy (E) to carboxyl groups, E/PA = 1, the main reaction was the carboxyl addition to the epoxy giving a β‐hydroxy ester. This reaction was followed by transesterification that occurred to a very small extent. In the formulations prepared with an epoxy excess, E/PA > 1, the transesterification reactions were very significant as well as the homopolymerization of the epoxy excess that took place to an almost complete conversion. Reaction products synthesized in the range of 1 < E/PA < 2 were solids at room temperature due to the crystallization of a fraction of fatty acid chains. Above the melting temperature, reaction products recovered the liquid state. The formulation synthesized with E/PA = 2 exhibited a good behavior as a hot‐melt adhesive of steel sheets with a single lap‐shear strength of 2.5 MPa and an interfacial‐cohesive failure. For E/PA > 3, the gelation took place leading to the networks exhibiting a single glass transition temperature (Tg) without any evidence of crystallization or phase separation. Tg varied from 90 °C for the neat epoxy to 0 °C for the formulation with E/PA = 3.
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: Galante, Maria 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
Fil: Oyanguren, Patricia Angelica. 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 Reactions taking place in a homogeneous solution of an epoxy monomer based on the diglycidyl ether of bisphenol A (DGEBA) and palmitic acid (PA), in the presence of benzyldimethylamine (BDMA), were investigated using Fourier‐transformed infrared spectroscopy (FTIR) and size exclusion chromatography (SEC). In the stoichiometric formulations prepared with equal molar ratios of epoxy (E) to carboxyl groups, E/PA = 1, the main reaction was the carboxyl addition to the epoxy giving a β‐hydroxy ester. This reaction was followed by transesterification that occurred to a very small extent. In the formulations prepared with an epoxy excess, E/PA > 1, the transesterification reactions were very significant as well as the homopolymerization of the epoxy excess that took place to an almost complete conversion. Reaction products synthesized in the range of 1 < E/PA < 2 were solids at room temperature due to the crystallization of a fraction of fatty acid chains. Above the melting temperature, reaction products recovered the liquid state. The formulation synthesized with E/PA = 2 exhibited a good behavior as a hot‐melt adhesive of steel sheets with a single lap‐shear strength of 2.5 MPa and an interfacial‐cohesive failure. For E/PA > 3, the gelation took place leading to the networks exhibiting a single glass transition temperature (Tg) without any evidence of crystallization or phase separation. Tg varied from 90 °C for the neat epoxy to 0 °C for the formulation with E/PA = 3.
publishDate 2005
dc.date.none.fl_str_mv 2005-05
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/11336/94725
Hoppe, Cristina Elena; Galante, Maria Jose; Oyanguren, Patricia Angelica; Williams, Roberto Juan Jose; Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks; Wiley VCH Verlag; Macromolecular Materials and Engineering (print); 290; 5; 5-2005; 456-462
1438-7492
CONICET Digital
CONICET
url http://hdl.handle.net/11336/94725
identifier_str_mv Hoppe, Cristina Elena; Galante, Maria Jose; Oyanguren, Patricia Angelica; Williams, Roberto Juan Jose; Epoxies modified by palmitic acid: From hot-melt adhesives to plasticized networks; Wiley VCH Verlag; Macromolecular Materials and Engineering (print); 290; 5; 5-2005; 456-462
1438-7492
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://onlinelibrary.wiley.com/doi/abs/10.1002/mame.200400348
info:eu-repo/semantics/altIdentifier/doi/10.1002/mame.200400348
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
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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