Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators

Metal-free catalysis was successfully applied to polymerize ω-pentadecalactone (PDL) by ring-opening polymerization (ROP) using several amino-ended initiators, namely hexylamine, allylamine and O,O′-bis(3-aminopropyl)diethylene glycol. This polymerization method was suitable to prepare telechelic po...

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Autores: Tinajero Díaz, Ernesto, Martínez de Ilarduya, Antxon, Muñoz Guerra, Sebastián, Paz Báñez, María Violante de, Galbis Fuster, Elsa
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Universidad de Sevilla (US)
Repositorio:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/135072
Acceso en línea:https://hdl.handle.net/11441/135072
https://doi.org/10.1016/j.eurpolymj.2018.09.006
Access Level:acceso abierto
Palabra clave:Amphiphilic block copolymer nanoparticles
Amphiphilic block copolymers
Enzymatic ring-opening polymerization
Macrolactones polymerization
Polyethyleneglycol-polyester copolymers
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spelling Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiatorsTinajero Díaz, ErnestoMartínez de Ilarduya, AntxonMuñoz Guerra, SebastiánPaz Báñez, María Violante deGalbis Fuster, ElsaAmphiphilic block copolymer nanoparticlesAmphiphilic block copolymersEnzymatic ring-opening polymerizationMacrolactones polymerizationPolyethyleneglycol-polyester copolymersMetal-free catalysis was successfully applied to polymerize ω-pentadecalactone (PDL) by ring-opening polymerization (ROP) using several amino-ended initiators, namely hexylamine, allylamine and O,O′-bis(3-aminopropyl)diethylene glycol. This polymerization method was suitable to prepare telechelic polyesters carrying functional-end groups. The technique was then extended to the synthesis of block copolymers by ROP of PDL using bisamino-ended poly(ethylene glycol) (Mn = 2600) as macroinitiator. PPDLx-PEG56-PPDLx triblock copolymers with Mn ranging between ∼4000 and ∼90,000 g ·mol−1 were synthesized and extensively characterized by NMR, DSC, TGA and XRD. The amphiphilic copolymers thus produced were demonstrated to be able to self-assemble in nanoparticles with average diameters of ∼100–200 nm and morphologies highly depending on blocks lengths. The described synthetic route distinguishes in providing “clean” amphiphilic copolymers, which are attractive candidates for biomedical applications.Ministerio de Economía y Competitividad MAT-2016- 77345-CO3-01, MAT-2016-77345-CO3-02ElsevierQuímica Orgánica y FarmacéuticaMinisterio de Economía y Competitividad (MINECO). España2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttps://hdl.handle.net/11441/135072https://doi.org/10.1016/j.eurpolymj.2018.09.006reponame:idUS. Depósito de Investigación de la Universidad de Sevillainstname:Universidad de Sevilla (US)InglésEuropean Polymer Journal, 108, 380-389.MAT-2016- 77345-CO3-01MAT-2016-77345-CO3-02https://doi.org/10.1016/j.eurpolymj.2018.09.006info:eu-repo/semantics/openAccessoai:idus.us.es:11441/1350722026-06-17T12:51:07Z
dc.title.none.fl_str_mv Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
title Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
spellingShingle Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
Tinajero Díaz, Ernesto
Amphiphilic block copolymer nanoparticles
Amphiphilic block copolymers
Enzymatic ring-opening polymerization
Macrolactones polymerization
Polyethyleneglycol-polyester copolymers
title_short Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
title_full Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
title_fullStr Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
title_full_unstemmed Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
title_sort Metal-free catalyzed ring-opening polymerization and block copolymerization of ω-pentadecalactone using amino-ended initiators
dc.creator.none.fl_str_mv Tinajero Díaz, Ernesto
Martínez de Ilarduya, Antxon
Muñoz Guerra, Sebastián
Paz Báñez, María Violante de
Galbis Fuster, Elsa
author Tinajero Díaz, Ernesto
author_facet Tinajero Díaz, Ernesto
Martínez de Ilarduya, Antxon
Muñoz Guerra, Sebastián
Paz Báñez, María Violante de
Galbis Fuster, Elsa
author_role author
author2 Martínez de Ilarduya, Antxon
Muñoz Guerra, Sebastián
Paz Báñez, María Violante de
Galbis Fuster, Elsa
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Química Orgánica y Farmacéutica
Ministerio de Economía y Competitividad (MINECO). España
dc.subject.none.fl_str_mv Amphiphilic block copolymer nanoparticles
Amphiphilic block copolymers
Enzymatic ring-opening polymerization
Macrolactones polymerization
Polyethyleneglycol-polyester copolymers
topic Amphiphilic block copolymer nanoparticles
Amphiphilic block copolymers
Enzymatic ring-opening polymerization
Macrolactones polymerization
Polyethyleneglycol-polyester copolymers
description Metal-free catalysis was successfully applied to polymerize ω-pentadecalactone (PDL) by ring-opening polymerization (ROP) using several amino-ended initiators, namely hexylamine, allylamine and O,O′-bis(3-aminopropyl)diethylene glycol. This polymerization method was suitable to prepare telechelic polyesters carrying functional-end groups. The technique was then extended to the synthesis of block copolymers by ROP of PDL using bisamino-ended poly(ethylene glycol) (Mn = 2600) as macroinitiator. PPDLx-PEG56-PPDLx triblock copolymers with Mn ranging between ∼4000 and ∼90,000 g ·mol−1 were synthesized and extensively characterized by NMR, DSC, TGA and XRD. The amphiphilic copolymers thus produced were demonstrated to be able to self-assemble in nanoparticles with average diameters of ∼100–200 nm and morphologies highly depending on blocks lengths. The described synthetic route distinguishes in providing “clean” amphiphilic copolymers, which are attractive candidates for biomedical applications.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/11441/135072
https://doi.org/10.1016/j.eurpolymj.2018.09.006
url https://hdl.handle.net/11441/135072
https://doi.org/10.1016/j.eurpolymj.2018.09.006
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv European Polymer Journal, 108, 380-389.
MAT-2016- 77345-CO3-01
MAT-2016-77345-CO3-02
https://doi.org/10.1016/j.eurpolymj.2018.09.006
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:idUS. Depósito de Investigación de la Universidad de Sevilla
instname:Universidad de Sevilla (US)
instname_str Universidad de Sevilla (US)
reponame_str idUS. Depósito de Investigación de la Universidad de Sevilla
collection idUS. Depósito de Investigación de la Universidad de Sevilla
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repository.mail.fl_str_mv
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