Synthesis and properties of cleavable quaternary ammonium compounds

Autores
Gilbert, Elangeni Ana; Guastavino, Javier Fernando; Nicollier, Rocío A.; Lancelle, María Verónica; Russell White, Karen; Murguia, Marcelo Cesar
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel amphiphilic molecules with similar properties to those already known but more biodegradable. Based on benzalkonium chloride (BAC), novel carbonate cleavable surfactants (CBAC) were synthesized. The breakable carbonate sites make CBAC compounds more degradable and potentially more biodegradable than their non-cleavable BAC analogues. Natural products such as fatty alcohols (C8-C16) and N,N-dimethyl- 2-aminoethanol were used as reagents for the synthesis of CBAC8-16. These amphiphilic compounds were characterized in terms of surface properties and antimicrobial activity against Gram-positive and Gramnegative bacteria, yeasts and moulds. The novel surfactants showed similar surface activities in aqueous solutions when compared to BAC. Also, the surface activity/structure relationship revealed that carbonate cleavable surfactants with n-decyl group (CBAC10) showed the same behaviour as non-cleavable BAC. Furthermore, compounds containing n-octyl (CBAC8), n-decyl (CBAC10) and n-dodecyl (CBAC12) group showed strong antimicrobial activities.
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: Guastavino, Javier Fernando. 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: Nicollier, Rocío A.. 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: Lancelle, María Verónica. Universidad Nacional del Litoral. Facultad de Ingeniería Química; Argentina
Fil: Russell White, Karen. Universidad Nacional del Litoral. Facultad de Ingeniería Química; Argentina
Fil: Murguia, Marcelo Cesar. 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
ANTIMICROBIAL ACTIVITY
CARBONATE
CLEAVABLE SURFACTANTS
QUATERNARY AMMONIUM
SURFACE ACTIVITY
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/164937
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/164937
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and properties of cleavable quaternary ammonium compoundsGilbert, Elangeni AnaGuastavino, Javier FernandoNicollier, Rocío A.Lancelle, María VerónicaRussell White, KarenMurguia, Marcelo CesarANTIMICROBIAL ACTIVITYCARBONATECLEAVABLE SURFACTANTSQUATERNARY AMMONIUMSURFACE ACTIVITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel amphiphilic molecules with similar properties to those already known but more biodegradable. Based on benzalkonium chloride (BAC), novel carbonate cleavable surfactants (CBAC) were synthesized. The breakable carbonate sites make CBAC compounds more degradable and potentially more biodegradable than their non-cleavable BAC analogues. Natural products such as fatty alcohols (C8-C16) and N,N-dimethyl- 2-aminoethanol were used as reagents for the synthesis of CBAC8-16. These amphiphilic compounds were characterized in terms of surface properties and antimicrobial activity against Gram-positive and Gramnegative bacteria, yeasts and moulds. The novel surfactants showed similar surface activities in aqueous solutions when compared to BAC. Also, the surface activity/structure relationship revealed that carbonate cleavable surfactants with n-decyl group (CBAC10) showed the same behaviour as non-cleavable BAC. Furthermore, compounds containing n-octyl (CBAC8), n-decyl (CBAC10) and n-dodecyl (CBAC12) group showed strong antimicrobial activities.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: Guastavino, Javier Fernando. 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: Nicollier, Rocío A.. 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: Lancelle, María Verónica. Universidad Nacional del Litoral. Facultad de Ingeniería Química; ArgentinaFil: Russell White, Karen. Universidad Nacional del Litoral. Facultad de Ingeniería Química; ArgentinaFil: Murguia, Marcelo Cesar. 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; ArgentinaJapan Oil Chemists’ Society2021-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/164937Gilbert, Elangeni Ana; Guastavino, Javier Fernando; Nicollier, Rocío A.; Lancelle, María Verónica; Russell White, Karen; et al.; Synthesis and properties of cleavable quaternary ammonium compounds; Japan Oil Chemists’ Society; Journal of Oleo Science; 70; 1; 3-2021; 59-651345-8957CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.jstage.jst.go.jp/article/jos/70/1/70_ess20216/_articleinfo:eu-repo/semantics/altIdentifier/doi/10.5650/jos.ess20216info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:01:14Zoai:ri.conicet.gov.ar:11336/164937instacron: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 13:01:14.504CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and properties of cleavable quaternary ammonium compounds
title Synthesis and properties of cleavable quaternary ammonium compounds
spellingShingle Synthesis and properties of cleavable quaternary ammonium compounds
Gilbert, Elangeni Ana
ANTIMICROBIAL ACTIVITY
CARBONATE
CLEAVABLE SURFACTANTS
QUATERNARY AMMONIUM
SURFACE ACTIVITY
title_short Synthesis and properties of cleavable quaternary ammonium compounds
title_full Synthesis and properties of cleavable quaternary ammonium compounds
title_fullStr Synthesis and properties of cleavable quaternary ammonium compounds
title_full_unstemmed Synthesis and properties of cleavable quaternary ammonium compounds
title_sort Synthesis and properties of cleavable quaternary ammonium compounds
dc.creator.none.fl_str_mv Gilbert, Elangeni Ana
Guastavino, Javier Fernando
Nicollier, Rocío A.
Lancelle, María Verónica
Russell White, Karen
Murguia, Marcelo Cesar
author Gilbert, Elangeni Ana
author_facet Gilbert, Elangeni Ana
Guastavino, Javier Fernando
Nicollier, Rocío A.
Lancelle, María Verónica
Russell White, Karen
Murguia, Marcelo Cesar
author_role author
author2 Guastavino, Javier Fernando
Nicollier, Rocío A.
Lancelle, María Verónica
Russell White, Karen
Murguia, Marcelo Cesar
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ANTIMICROBIAL ACTIVITY
CARBONATE
CLEAVABLE SURFACTANTS
QUATERNARY AMMONIUM
SURFACE ACTIVITY
topic ANTIMICROBIAL ACTIVITY
CARBONATE
CLEAVABLE SURFACTANTS
QUATERNARY AMMONIUM
SURFACE ACTIVITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel amphiphilic molecules with similar properties to those already known but more biodegradable. Based on benzalkonium chloride (BAC), novel carbonate cleavable surfactants (CBAC) were synthesized. The breakable carbonate sites make CBAC compounds more degradable and potentially more biodegradable than their non-cleavable BAC analogues. Natural products such as fatty alcohols (C8-C16) and N,N-dimethyl- 2-aminoethanol were used as reagents for the synthesis of CBAC8-16. These amphiphilic compounds were characterized in terms of surface properties and antimicrobial activity against Gram-positive and Gramnegative bacteria, yeasts and moulds. The novel surfactants showed similar surface activities in aqueous solutions when compared to BAC. Also, the surface activity/structure relationship revealed that carbonate cleavable surfactants with n-decyl group (CBAC10) showed the same behaviour as non-cleavable BAC. Furthermore, compounds containing n-octyl (CBAC8), n-decyl (CBAC10) and n-dodecyl (CBAC12) group showed strong antimicrobial activities.
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: Guastavino, Javier Fernando. 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: Nicollier, Rocío A.. 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: Lancelle, María Verónica. Universidad Nacional del Litoral. Facultad de Ingeniería Química; Argentina
Fil: Russell White, Karen. Universidad Nacional del Litoral. Facultad de Ingeniería Química; Argentina
Fil: Murguia, Marcelo Cesar. 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 Quaternary ammonium compounds are widely used as antiseptic and disinfectant. It is been a concern that their widespread use will lead to an increase of environmental problems, therefore the development of biodegradable surfactants is necessary. The present research is aimed at the design of novel amphiphilic molecules with similar properties to those already known but more biodegradable. Based on benzalkonium chloride (BAC), novel carbonate cleavable surfactants (CBAC) were synthesized. The breakable carbonate sites make CBAC compounds more degradable and potentially more biodegradable than their non-cleavable BAC analogues. Natural products such as fatty alcohols (C8-C16) and N,N-dimethyl- 2-aminoethanol were used as reagents for the synthesis of CBAC8-16. These amphiphilic compounds were characterized in terms of surface properties and antimicrobial activity against Gram-positive and Gramnegative bacteria, yeasts and moulds. The novel surfactants showed similar surface activities in aqueous solutions when compared to BAC. Also, the surface activity/structure relationship revealed that carbonate cleavable surfactants with n-decyl group (CBAC10) showed the same behaviour as non-cleavable BAC. Furthermore, compounds containing n-octyl (CBAC8), n-decyl (CBAC10) and n-dodecyl (CBAC12) group showed strong antimicrobial activities.
publishDate 2021
dc.date.none.fl_str_mv 2021-03
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/11336/164937
Gilbert, Elangeni Ana; Guastavino, Javier Fernando; Nicollier, Rocío A.; Lancelle, María Verónica; Russell White, Karen; et al.; Synthesis and properties of cleavable quaternary ammonium compounds; Japan Oil Chemists’ Society; Journal of Oleo Science; 70; 1; 3-2021; 59-65
1345-8957
CONICET Digital
CONICET
url http://hdl.handle.net/11336/164937
identifier_str_mv Gilbert, Elangeni Ana; Guastavino, Javier Fernando; Nicollier, Rocío A.; Lancelle, María Verónica; Russell White, Karen; et al.; Synthesis and properties of cleavable quaternary ammonium compounds; Japan Oil Chemists’ Society; Journal of Oleo Science; 70; 1; 3-2021; 59-65
1345-8957
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://www.jstage.jst.go.jp/article/jos/70/1/70_ess20216/_article
info:eu-repo/semantics/altIdentifier/doi/10.5650/jos.ess20216
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Japan Oil Chemists’ Society
publisher.none.fl_str_mv Japan Oil Chemists’ Society
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_ 1842979935101124608
score 12.48226

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