From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation

Autores
Petton, Lionel; Ciolino, Andrés Eduardo; Dervaux, Bart; Du Prez, Filip E.
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6- tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2- dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.
Fil: Petton, Lionel. University of Ghent; Bélgica
Fil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Dervaux, Bart. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
Materia
Nmp
Atrp
Controlled Radical Polymerization
Chain Transfer Agents
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:11336/77178
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisationPetton, LionelCiolino, Andrés EduardoDervaux, BartDu Prez, Filip E.NmpAtrpControlled Radical PolymerizationChain Transfer Agentshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6- tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2- dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.Fil: Petton, Lionel. University of Ghent; BélgicaFil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; ArgentinaFil: Dervaux, Bart. University of Ghent; BélgicaFil: Du Prez, Filip E.. University of Ghent; BélgicaRoyal Society of Chemistry2012-07-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/77178Petton, Lionel; Ciolino, Andrés Eduardo; Dervaux, Bart; Du Prez, Filip E.; From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation; Royal Society of Chemistry; Polymer Chemistry; 3; 7; 3-7-2012; 1867-18781759-99541759-9962CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2012/PY/c2py00444e#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/c2py00444einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:24:21Zoai:ri.conicet.gov.ar:11336/77178instacron: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 13:24:21.677CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
title From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
spellingShingle From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
Petton, Lionel
Nmp
Atrp
Controlled Radical Polymerization
Chain Transfer Agents
title_short From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
title_full From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
title_fullStr From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
title_full_unstemmed From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
title_sort From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation
dc.creator.none.fl_str_mv Petton, Lionel
Ciolino, Andrés Eduardo
Dervaux, Bart
Du Prez, Filip E.
author Petton, Lionel
author_facet Petton, Lionel
Ciolino, Andrés Eduardo
Dervaux, Bart
Du Prez, Filip E.
author_role author
author2 Ciolino, Andrés Eduardo
Dervaux, Bart
Du Prez, Filip E.
author2_role author
author
author
dc.subject.none.fl_str_mv Nmp
Atrp
Controlled Radical Polymerization
Chain Transfer Agents
topic Nmp
Atrp
Controlled Radical Polymerization
Chain Transfer Agents
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6- tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2- dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.
Fil: Petton, Lionel. University of Ghent; Bélgica
Fil: Ciolino, Andrés Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Planta Piloto de Ingeniería Química. Universidad Nacional del Sur. Planta Piloto de Ingeniería Química; Argentina
Fil: Dervaux, Bart. University of Ghent; Bélgica
Fil: Du Prez, Filip E.. University of Ghent; Bélgica
description A one-pot controlled method for the nitroxide end-group removal from synthetic polymers prepared by nitroxide mediated polymerisation (NMP) is reported. The strategy relies on the controlled addition of compounds such as thiols, radical initiators and carbon tetrabromide with high chain transfer constants. From a practical point of view, when the desired molar mass and conversion are reached, 1 to 10 equivalents of the transfer agent compared to the nitroxide are added and a few minutes later, after transformation of all chain-ends, the reaction is quenched. The versatility of the procedure was successfully tested with a wide range of monomers (styrene (S), isobornyl acrylate (iBA) or methyl methacrylate (MMA)) and nitroxides (2,2,6,6- tetramethyl-1-piperidinyloxy (TEMPO) and N-tert-butyl-1-diethylphosphono-2,2- dimethylpropyl nitroxide (SG1)). The removal of the nitroxide end-group proceeds with high fidelity for all the transfer agents studied, while at the same time the thermal stability of the resulting polymer chains increases when thiols are employed. Furthermore, a functional group that allows for chain extension by atom transfer radical polymerisation (ATRP) has been introduced through the direct synthesis of bromine terminated macroinitiators via a chain transfer reaction with carbon tetrabromide.
publishDate 2012
dc.date.none.fl_str_mv 2012-07-03
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/11336/77178
Petton, Lionel; Ciolino, Andrés Eduardo; Dervaux, Bart; Du Prez, Filip E.; From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation; Royal Society of Chemistry; Polymer Chemistry; 3; 7; 3-7-2012; 1867-1878
1759-9954
1759-9962
CONICET Digital
CONICET
url http://hdl.handle.net/11336/77178
identifier_str_mv Petton, Lionel; Ciolino, Andrés Eduardo; Dervaux, Bart; Du Prez, Filip E.; From one-pot stabilisation to in situ functionalisation in nitroxide mediated polymerisation: An efficient extension towards atom transfer radical polymerisation; Royal Society of Chemistry; Polymer Chemistry; 3; 7; 3-7-2012; 1867-1878
1759-9954
1759-9962
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://pubs.rsc.org/en/content/articlelanding/2012/PY/c2py00444e#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/c2py00444e
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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_ 1842981350208962560
score 12.48226

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