Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study

Autores
Gomez, María Lorena; Palacios, Rodrigo Emiliano; Previtali, Carlos Mario; Montejano, Hernan Alfredo; Chesta, Carlos Alberto
Año de publicación
2002
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
N-Dimethyl-N-[2-(N,N-dimethylamino)ethyl]-N-(1-methylnaphthyl)ammonium tetrafluoroborate (I) was synthesized with the aim of obtaining a versatile photoinitiator for vinyl polymerization in organic solvents and water. Salt I was able to trigger the polymerization of acrylamide, 2-hydroxyethylmethacrylate and styrene even at very low concentrations of the salt (∼1.0 × 10-5 M). Using laser flash photolysis and fluorescence techniques and analyzing the photoproduct distribution, we were able to postulate a mechanism for the photodecomposition of the salt. With irradiation, I undergoes an intramolecular electron-transfer reaction to form a radical ion pair (RIP). The RIP intermediate decomposes into free radicals. The RIP and the free radicals are active species for initiating the polymerization. Depending on the concentration of the vinyl monomers studied, the initiation mechanism of the polymerization reaction changes. At large monomer concentrations, the RIP state is postulated to trigger the reaction by generating the anion radical of the olefin substrate. At a low monomer concentration, the free radicals produced by the decomposition of I are believed to start the chain reaction.
Fil: Gomez, María Lorena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Previtali, Carlos Mario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Chesta, Carlos Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Materia
Charge Transfer
Initiators
Photopolymerization
Radical Polymerization
Tetraalkylammonium Salt
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:11336/78313
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/78313
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis studyGomez, María LorenaPalacios, Rodrigo EmilianoPrevitali, Carlos MarioMontejano, Hernan AlfredoChesta, Carlos AlbertoCharge TransferInitiatorsPhotopolymerizationRadical PolymerizationTetraalkylammonium Salthttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1N-Dimethyl-N-[2-(N,N-dimethylamino)ethyl]-N-(1-methylnaphthyl)ammonium tetrafluoroborate (I) was synthesized with the aim of obtaining a versatile photoinitiator for vinyl polymerization in organic solvents and water. Salt I was able to trigger the polymerization of acrylamide, 2-hydroxyethylmethacrylate and styrene even at very low concentrations of the salt (∼1.0 × 10-5 M). Using laser flash photolysis and fluorescence techniques and analyzing the photoproduct distribution, we were able to postulate a mechanism for the photodecomposition of the salt. With irradiation, I undergoes an intramolecular electron-transfer reaction to form a radical ion pair (RIP). The RIP intermediate decomposes into free radicals. The RIP and the free radicals are active species for initiating the polymerization. Depending on the concentration of the vinyl monomers studied, the initiation mechanism of the polymerization reaction changes. At large monomer concentrations, the RIP state is postulated to trigger the reaction by generating the anion radical of the olefin substrate. At a low monomer concentration, the free radicals produced by the decomposition of I are believed to start the chain reaction.Fil: Gomez, María Lorena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Previtali, Carlos Mario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Chesta, Carlos Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaJohn Wiley & Sons Inc2002-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/78313Gomez, María Lorena; Palacios, Rodrigo Emiliano; Previtali, Carlos Mario; Montejano, Hernan Alfredo; Chesta, Carlos Alberto; Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study; John Wiley & Sons Inc; Journal of Polymer Science Part A: Polymer Chemistry; 40; 7; 4-2002; 901-9130887-624XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/pola.10166info:eu-repo/semantics/altIdentifier/doi/10.1002/pola.10166info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:38:12Zoai:ri.conicet.gov.ar:11336/78313instacron: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 14:38:13.233CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
title Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
spellingShingle Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
Gomez, María Lorena
Charge Transfer
Initiators
Photopolymerization
Radical Polymerization
Tetraalkylammonium Salt
title_short Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
title_full Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
title_fullStr Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
title_full_unstemmed Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
title_sort Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study
dc.creator.none.fl_str_mv Gomez, María Lorena
Palacios, Rodrigo Emiliano
Previtali, Carlos Mario
Montejano, Hernan Alfredo
Chesta, Carlos Alberto
author Gomez, María Lorena
author_facet Gomez, María Lorena
Palacios, Rodrigo Emiliano
Previtali, Carlos Mario
Montejano, Hernan Alfredo
Chesta, Carlos Alberto
author_role author
author2 Palacios, Rodrigo Emiliano
Previtali, Carlos Mario
Montejano, Hernan Alfredo
Chesta, Carlos Alberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv Charge Transfer
Initiators
Photopolymerization
Radical Polymerization
Tetraalkylammonium Salt
topic Charge Transfer
Initiators
Photopolymerization
Radical Polymerization
Tetraalkylammonium Salt
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv N-Dimethyl-N-[2-(N,N-dimethylamino)ethyl]-N-(1-methylnaphthyl)ammonium tetrafluoroborate (I) was synthesized with the aim of obtaining a versatile photoinitiator for vinyl polymerization in organic solvents and water. Salt I was able to trigger the polymerization of acrylamide, 2-hydroxyethylmethacrylate and styrene even at very low concentrations of the salt (∼1.0 × 10-5 M). Using laser flash photolysis and fluorescence techniques and analyzing the photoproduct distribution, we were able to postulate a mechanism for the photodecomposition of the salt. With irradiation, I undergoes an intramolecular electron-transfer reaction to form a radical ion pair (RIP). The RIP intermediate decomposes into free radicals. The RIP and the free radicals are active species for initiating the polymerization. Depending on the concentration of the vinyl monomers studied, the initiation mechanism of the polymerization reaction changes. At large monomer concentrations, the RIP state is postulated to trigger the reaction by generating the anion radical of the olefin substrate. At a low monomer concentration, the free radicals produced by the decomposition of I are believed to start the chain reaction.
Fil: Gomez, María Lorena. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Palacios, Rodrigo Emiliano. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Previtali, Carlos Mario. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Montejano, Hernan Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Chesta, Carlos Alberto. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
description N-Dimethyl-N-[2-(N,N-dimethylamino)ethyl]-N-(1-methylnaphthyl)ammonium tetrafluoroborate (I) was synthesized with the aim of obtaining a versatile photoinitiator for vinyl polymerization in organic solvents and water. Salt I was able to trigger the polymerization of acrylamide, 2-hydroxyethylmethacrylate and styrene even at very low concentrations of the salt (∼1.0 × 10-5 M). Using laser flash photolysis and fluorescence techniques and analyzing the photoproduct distribution, we were able to postulate a mechanism for the photodecomposition of the salt. With irradiation, I undergoes an intramolecular electron-transfer reaction to form a radical ion pair (RIP). The RIP intermediate decomposes into free radicals. The RIP and the free radicals are active species for initiating the polymerization. Depending on the concentration of the vinyl monomers studied, the initiation mechanism of the polymerization reaction changes. At large monomer concentrations, the RIP state is postulated to trigger the reaction by generating the anion radical of the olefin substrate. At a low monomer concentration, the free radicals produced by the decomposition of I are believed to start the chain reaction.
publishDate 2002
dc.date.none.fl_str_mv 2002-04
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/11336/78313
Gomez, María Lorena; Palacios, Rodrigo Emiliano; Previtali, Carlos Mario; Montejano, Hernan Alfredo; Chesta, Carlos Alberto; Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study; John Wiley & Sons Inc; Journal of Polymer Science Part A: Polymer Chemistry; 40; 7; 4-2002; 901-913
0887-624X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/78313
identifier_str_mv Gomez, María Lorena; Palacios, Rodrigo Emiliano; Previtali, Carlos Mario; Montejano, Hernan Alfredo; Chesta, Carlos Alberto; Tetraalkylammonium salt as photoinitiator of vinyl polymerization in organic and aqueous media: A mechanistic and laser flash photolysis study; John Wiley & Sons Inc; Journal of Polymer Science Part A: Polymer Chemistry; 40; 7; 4-2002; 901-913
0887-624X
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/pola.10166
info:eu-repo/semantics/altIdentifier/doi/10.1002/pola.10166
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
dc.publisher.none.fl_str_mv John Wiley & Sons Inc
publisher.none.fl_str_mv John Wiley & Sons Inc
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
_version_ 1846082860166938624
score 13.22299

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