Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes

Autores
Arce, Silvina M.; Kolender, Adriana Andrea; Varela, Oscar Jose
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the conditions employed do not seem to be suitable for highly functionalized monomers. In contrast, the polymerization of ω-amino-α-phenylcarbonate alkanes is expected to occur under milder conditions. ω-Amino-α-phenylcarbonate alkanes have been synthesized from 6-aminohexanol (1) and 3-aminopropanol (6). The procedure involves the N-Boc protection of the amino group, followed by activation of the alcohol. Removal of the N-Boc affords the corresponding ω-amino-1-O-phenyloxycarbonyloxyalkane hydrochlorides. Other oligomeric comonomers between 1 and 6 have been prepared. The polymerization of these precursors takes place in the absence of metal catalysts to afford the corresponding linear and regioregular [n]-polyurethanes. The procedure described is useful for the preparation of stable ω-amino-α-phenylcarbonate alkane derivatives, which possess varied chain lengths between the terminal functions. These monomers yield [n]-polyurethanes having various structures starting from just two aminoalkanols. The polyurethanes were obtained in high yields, with reasonable molecular weight and polydispersity values, and they were characterized spectroscopically and thermally. These studies reveal constitutionally uniform structures that are free of carbonate or urea linkages.
Fil: Arce, Silvina M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
Ω-Amino-Α-Phenylcarbonate Alkanes
Aminoalkanols
Polymerization
Polyurethanes
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:11336/68840
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/68840
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanesArce, Silvina M.Kolender, Adriana AndreaVarela, Oscar JoseΩ-Amino-Α-Phenylcarbonate AlkanesAminoalkanolsPolymerizationPolyurethaneshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the conditions employed do not seem to be suitable for highly functionalized monomers. In contrast, the polymerization of ω-amino-α-phenylcarbonate alkanes is expected to occur under milder conditions. ω-Amino-α-phenylcarbonate alkanes have been synthesized from 6-aminohexanol (1) and 3-aminopropanol (6). The procedure involves the N-Boc protection of the amino group, followed by activation of the alcohol. Removal of the N-Boc affords the corresponding ω-amino-1-O-phenyloxycarbonyloxyalkane hydrochlorides. Other oligomeric comonomers between 1 and 6 have been prepared. The polymerization of these precursors takes place in the absence of metal catalysts to afford the corresponding linear and regioregular [n]-polyurethanes. The procedure described is useful for the preparation of stable ω-amino-α-phenylcarbonate alkane derivatives, which possess varied chain lengths between the terminal functions. These monomers yield [n]-polyurethanes having various structures starting from just two aminoalkanols. The polyurethanes were obtained in high yields, with reasonable molecular weight and polydispersity values, and they were characterized spectroscopically and thermally. These studies reveal constitutionally uniform structures that are free of carbonate or urea linkages.Fil: Arce, Silvina M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; ArgentinaJohn Wiley & Sons Ltd2010-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/68840Arce, Silvina M.; Kolender, Adriana Andrea; Varela, Oscar Jose; Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes; John Wiley & Sons Ltd; Polymer International; 59; 9; 9-2010; 1212-12200959-8103CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/pi.2850info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/pi.2850info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T12:08:12Zoai:ri.conicet.gov.ar:11336/68840instacron: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:34982025-10-22 12:08:12.373CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
title Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
spellingShingle Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
Arce, Silvina M.
Ω-Amino-Α-Phenylcarbonate Alkanes
Aminoalkanols
Polymerization
Polyurethanes
title_short Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
title_full Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
title_fullStr Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
title_full_unstemmed Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
title_sort Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes
dc.creator.none.fl_str_mv Arce, Silvina M.
Kolender, Adriana Andrea
Varela, Oscar Jose
author Arce, Silvina M.
author_facet Arce, Silvina M.
Kolender, Adriana Andrea
Varela, Oscar Jose
author_role author
author2 Kolender, Adriana Andrea
Varela, Oscar Jose
author2_role author
author
dc.subject.none.fl_str_mv Ω-Amino-Α-Phenylcarbonate Alkanes
Aminoalkanols
Polymerization
Polyurethanes
topic Ω-Amino-Α-Phenylcarbonate Alkanes
Aminoalkanols
Polymerization
Polyurethanes
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the conditions employed do not seem to be suitable for highly functionalized monomers. In contrast, the polymerization of ω-amino-α-phenylcarbonate alkanes is expected to occur under milder conditions. ω-Amino-α-phenylcarbonate alkanes have been synthesized from 6-aminohexanol (1) and 3-aminopropanol (6). The procedure involves the N-Boc protection of the amino group, followed by activation of the alcohol. Removal of the N-Boc affords the corresponding ω-amino-1-O-phenyloxycarbonyloxyalkane hydrochlorides. Other oligomeric comonomers between 1 and 6 have been prepared. The polymerization of these precursors takes place in the absence of metal catalysts to afford the corresponding linear and regioregular [n]-polyurethanes. The procedure described is useful for the preparation of stable ω-amino-α-phenylcarbonate alkane derivatives, which possess varied chain lengths between the terminal functions. These monomers yield [n]-polyurethanes having various structures starting from just two aminoalkanols. The polyurethanes were obtained in high yields, with reasonable molecular weight and polydispersity values, and they were characterized spectroscopically and thermally. These studies reveal constitutionally uniform structures that are free of carbonate or urea linkages.
Fil: Arce, Silvina M.. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Kolender, Adriana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
description Aliphatic [n]-polyurethanes have recently been synthesized from ω-isocyanato-α-alkanols or, more traditionally, by cationic ring-opening polymerization of cyclourethanes or by the Bu2Sn(OMe)2-promoted polycondensation of ω-hydroxy-α-O- phenylurethane alkanes. For the latter procedures, the conditions employed do not seem to be suitable for highly functionalized monomers. In contrast, the polymerization of ω-amino-α-phenylcarbonate alkanes is expected to occur under milder conditions. ω-Amino-α-phenylcarbonate alkanes have been synthesized from 6-aminohexanol (1) and 3-aminopropanol (6). The procedure involves the N-Boc protection of the amino group, followed by activation of the alcohol. Removal of the N-Boc affords the corresponding ω-amino-1-O-phenyloxycarbonyloxyalkane hydrochlorides. Other oligomeric comonomers between 1 and 6 have been prepared. The polymerization of these precursors takes place in the absence of metal catalysts to afford the corresponding linear and regioregular [n]-polyurethanes. The procedure described is useful for the preparation of stable ω-amino-α-phenylcarbonate alkane derivatives, which possess varied chain lengths between the terminal functions. These monomers yield [n]-polyurethanes having various structures starting from just two aminoalkanols. The polyurethanes were obtained in high yields, with reasonable molecular weight and polydispersity values, and they were characterized spectroscopically and thermally. These studies reveal constitutionally uniform structures that are free of carbonate or urea linkages.
publishDate 2010
dc.date.none.fl_str_mv 2010-09
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/11336/68840
Arce, Silvina M.; Kolender, Adriana Andrea; Varela, Oscar Jose; Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes; John Wiley & Sons Ltd; Polymer International; 59; 9; 9-2010; 1212-1220
0959-8103
CONICET Digital
CONICET
url http://hdl.handle.net/11336/68840
identifier_str_mv Arce, Silvina M.; Kolender, Adriana Andrea; Varela, Oscar Jose; Synthesis of ω-amino-α-phenylcarbonate alkanes and their polymerization to [n]-polyurethanes; John Wiley & Sons Ltd; Polymer International; 59; 9; 9-2010; 1212-1220
0959-8103
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/pi.2850
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/pi.2850
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 John Wiley & Sons Ltd
publisher.none.fl_str_mv John Wiley & Sons Ltd
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 12.952699

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