Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network

Autores
Gilbert, Elangeni Ana; Taverna, María Eugenia; Dieser, M.F.; Morales, G.; Spontón, Marisa Elisabet; Estenoz, Diana Alejandra
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this work, novel thermosetting systems of high performance based on multi-functional benzoxazines were developed. First, 3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3-benzoxazine (BzOH) and bis(3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3- benzoxazinyl) isopropane (BzPOH) monomers were synthesized by reaction between phenol or bisphenol A, paraformaldehyde, and ethanolamine. Then, BzOH and BzPOH were functionalized with maleic anhydride using a stoichiometric ratio of oxazine: maleic anhydride (1:1) to produce low molar mass species with carboxylic acid groups, named BzFA and BzPFA. The products were characterized by Nuclear Magnetic Resonance (NMR), Size-Exclusion Chromatography (SEC), and Fourier Transform Infrared Spectroscopy (FTIR). BzFA and BzPFA exhibited weight-average molecular weights of 5000 g.mol−1and 50,000 g.mol−1, respectively. Mixtures between the new precursors and the conventional benzoxazine (BzBA) derived from bisphenol A and aniline [bis(3-phenyl-3,4-dihydro-2H-1,3benzoxazinyl) isopropane] were prepared. The curing process was studied by FTIR and Differential Scanning Calorimetry (DSC), and viscoelastic, mechanical, thermal, and morphological properties of the materials were also evaluated. Materials obtained exhibited better thermal, viscoelastic and mechanical properties than conventional polybenzoxazine. Scanning Electron Microscope (SEM) measurements indicated homogeneous material surfaces.
Fil: Gilbert, Elangeni Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Taverna, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Dieser, M.F.. Universidad Nacional del Litoral; Argentina
Fil: Morales, G.. Centro de Investigacion En Quimica Aplicada, Saltillo; México
Fil: Spontón, Marisa Elisabet. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Estenoz, Diana Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Materia
Benzoxazines
Maleic anhydride
Thermal properties
Thermosets
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:11336/86716
Acceder
id CONICETDig_d1e8f62bddb5e0bd194d9ce90f7f3ac8
oai_identifier_str oai:ri.conicet.gov.ar:11336/86716
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the networkGilbert, Elangeni AnaTaverna, María EugeniaDieser, M.F.Morales, G.Spontón, Marisa ElisabetEstenoz, Diana AlejandraBenzoxazinesMaleic anhydrideThermal propertiesThermosetshttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2In this work, novel thermosetting systems of high performance based on multi-functional benzoxazines were developed. First, 3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3-benzoxazine (BzOH) and bis(3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3- benzoxazinyl) isopropane (BzPOH) monomers were synthesized by reaction between phenol or bisphenol A, paraformaldehyde, and ethanolamine. Then, BzOH and BzPOH were functionalized with maleic anhydride using a stoichiometric ratio of oxazine: maleic anhydride (1:1) to produce low molar mass species with carboxylic acid groups, named BzFA and BzPFA. The products were characterized by Nuclear Magnetic Resonance (NMR), Size-Exclusion Chromatography (SEC), and Fourier Transform Infrared Spectroscopy (FTIR). BzFA and BzPFA exhibited weight-average molecular weights of 5000 g.mol−1and 50,000 g.mol−1, respectively. Mixtures between the new precursors and the conventional benzoxazine (BzBA) derived from bisphenol A and aniline [bis(3-phenyl-3,4-dihydro-2H-1,3benzoxazinyl) isopropane] were prepared. The curing process was studied by FTIR and Differential Scanning Calorimetry (DSC), and viscoelastic, mechanical, thermal, and morphological properties of the materials were also evaluated. Materials obtained exhibited better thermal, viscoelastic and mechanical properties than conventional polybenzoxazine. Scanning Electron Microscope (SEM) measurements indicated homogeneous material surfaces.Fil: Gilbert, Elangeni Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Taverna, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Dieser, M.F.. Universidad Nacional del Litoral; ArgentinaFil: Morales, G.. Centro de Investigacion En Quimica Aplicada, Saltillo; MéxicoFil: Spontón, Marisa Elisabet. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaFil: Estenoz, Diana Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; ArgentinaSpringer2018-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/86716Gilbert, Elangeni Ana; Taverna, María Eugenia; Dieser, M.F.; Morales, G.; Spontón, Marisa Elisabet; et al.; Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network; Springer; Journal of Polymer Research; 25; 5; 5-2018; 1-121022-9760CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1007/s10965-018-1501-yinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:47:24Zoai:ri.conicet.gov.ar:11336/86716instacron: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:34982025-10-15 14:47:24.848CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
title Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
spellingShingle Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
Gilbert, Elangeni Ana
Benzoxazines
Maleic anhydride
Thermal properties
Thermosets
title_short Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
title_full Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
title_fullStr Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
title_full_unstemmed Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
title_sort Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network
dc.creator.none.fl_str_mv Gilbert, Elangeni Ana
Taverna, María Eugenia
Dieser, M.F.
Morales, G.
Spontón, Marisa Elisabet
Estenoz, Diana Alejandra
author Gilbert, Elangeni Ana
author_facet Gilbert, Elangeni Ana
Taverna, María Eugenia
Dieser, M.F.
Morales, G.
Spontón, Marisa Elisabet
Estenoz, Diana Alejandra
author_role author
author2 Taverna, María Eugenia
Dieser, M.F.
Morales, G.
Spontón, Marisa Elisabet
Estenoz, Diana Alejandra
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Benzoxazines
Maleic anhydride
Thermal properties
Thermosets
topic Benzoxazines
Maleic anhydride
Thermal properties
Thermosets
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In this work, novel thermosetting systems of high performance based on multi-functional benzoxazines were developed. First, 3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3-benzoxazine (BzOH) and bis(3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3- benzoxazinyl) isopropane (BzPOH) monomers were synthesized by reaction between phenol or bisphenol A, paraformaldehyde, and ethanolamine. Then, BzOH and BzPOH were functionalized with maleic anhydride using a stoichiometric ratio of oxazine: maleic anhydride (1:1) to produce low molar mass species with carboxylic acid groups, named BzFA and BzPFA. The products were characterized by Nuclear Magnetic Resonance (NMR), Size-Exclusion Chromatography (SEC), and Fourier Transform Infrared Spectroscopy (FTIR). BzFA and BzPFA exhibited weight-average molecular weights of 5000 g.mol−1and 50,000 g.mol−1, respectively. Mixtures between the new precursors and the conventional benzoxazine (BzBA) derived from bisphenol A and aniline [bis(3-phenyl-3,4-dihydro-2H-1,3benzoxazinyl) isopropane] were prepared. The curing process was studied by FTIR and Differential Scanning Calorimetry (DSC), and viscoelastic, mechanical, thermal, and morphological properties of the materials were also evaluated. Materials obtained exhibited better thermal, viscoelastic and mechanical properties than conventional polybenzoxazine. Scanning Electron Microscope (SEM) measurements indicated homogeneous material surfaces.
Fil: Gilbert, Elangeni Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Taverna, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Dieser, M.F.. Universidad Nacional del Litoral; Argentina
Fil: Morales, G.. Centro de Investigacion En Quimica Aplicada, Saltillo; México
Fil: Spontón, Marisa Elisabet. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
Fil: Estenoz, Diana Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe. Instituto de Desarrollo Tecnológico para la Industria Química. Universidad Nacional del Litoral. Instituto de Desarrollo Tecnológico para la Industria Química; Argentina
description In this work, novel thermosetting systems of high performance based on multi-functional benzoxazines were developed. First, 3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3-benzoxazine (BzOH) and bis(3-(2-hydroxyethyl)-3,4-dihydro-2H-1,3- benzoxazinyl) isopropane (BzPOH) monomers were synthesized by reaction between phenol or bisphenol A, paraformaldehyde, and ethanolamine. Then, BzOH and BzPOH were functionalized with maleic anhydride using a stoichiometric ratio of oxazine: maleic anhydride (1:1) to produce low molar mass species with carboxylic acid groups, named BzFA and BzPFA. The products were characterized by Nuclear Magnetic Resonance (NMR), Size-Exclusion Chromatography (SEC), and Fourier Transform Infrared Spectroscopy (FTIR). BzFA and BzPFA exhibited weight-average molecular weights of 5000 g.mol−1and 50,000 g.mol−1, respectively. Mixtures between the new precursors and the conventional benzoxazine (BzBA) derived from bisphenol A and aniline [bis(3-phenyl-3,4-dihydro-2H-1,3benzoxazinyl) isopropane] were prepared. The curing process was studied by FTIR and Differential Scanning Calorimetry (DSC), and viscoelastic, mechanical, thermal, and morphological properties of the materials were also evaluated. Materials obtained exhibited better thermal, viscoelastic and mechanical properties than conventional polybenzoxazine. Scanning Electron Microscope (SEM) measurements indicated homogeneous material surfaces.
publishDate 2018
dc.date.none.fl_str_mv 2018-05
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/11336/86716
Gilbert, Elangeni Ana; Taverna, María Eugenia; Dieser, M.F.; Morales, G.; Spontón, Marisa Elisabet; et al.; Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network; Springer; Journal of Polymer Research; 25; 5; 5-2018; 1-12
1022-9760
CONICET Digital
CONICET
url http://hdl.handle.net/11336/86716
identifier_str_mv Gilbert, Elangeni Ana; Taverna, María Eugenia; Dieser, M.F.; Morales, G.; Spontón, Marisa Elisabet; et al.; Synthesis and characterization of new thermosetting polybenzoxazines with other functional groups in the network; Springer; Journal of Polymer Research; 25; 5; 5-2018; 1-12
1022-9760
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1007/s10965-018-1501-y
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 Springer
publisher.none.fl_str_mv Springer
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 13.22299

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