Article (Scientific journals)
Ring-Opening Polymerization of 1,4,8-Trioxaspiro[4.6]-9-undecanone: A new Route to Aliphatic Polyesters Bearing Functional Pendent Groups
Tian, Dong; Dubois, Philippe; Grandfils, Christian et al.
1997In Macromolecules, 30 (3), p. 406-409
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Keywords :
ring-opening polymerization (ROP); lactone
Abstract :
[en] A straightforward and very efficient pathway has been reported for the synthesis of a functional derivative of ε-caprolactone, i.e. 5-ethylene ketal ε-caprolactone. This new monomer has been homopolymerized and copolymerized with ε-caprolactone in a well-controlled manner, strongly suggesting absence of any side reactions. Deacetalization of the polyester chains is complete and reduction of the ketone groups into hydroxyl groups as well. No chain scission is observed to occur in the course of these two derivatization reactions. Thus, aliphatic polyesters bearing either ketone pendent groups or hydroxyl pendent groups can be easily prepared, which raises new application prospects. These materials proved to be easily redispersed in an aqueous medium. They form stable colloidal nanodispersions (e.g. 100 nm). These suspensions are stable more than 48 h at room temperature and may be viewed as potential drug colloidal vectors with a core−shell like structure. Different types of reactive groups on the surface of these nanoparticulate vectors are indeed available to the binding of species selected for molecular recognition and drug targeting. For instance, the well-known reactivity of ketones toward primary amines is a direct route to attach peptides onto biodegradable and biocompatible aliphatic polyesters. Poly(ε-caprolactone) with hydroxyl groups reactive toward triethylaluminum provides a macroinitiator for lactone and lactide polymerization, so that biodegradable and biocompatible functional comb, graft, and dendritic aliphatic polyesters can now be synthesized.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry
Materials science & engineering
Author, co-author :
Tian, Dong;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Dubois, Philippe ;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Grandfils, Christian ;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Robert ;  Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Ring-Opening Polymerization of 1,4,8-Trioxaspiro[4.6]-9-undecanone: A new Route to Aliphatic Polyesters Bearing Functional Pendent Groups
Publication date :
10 February 1997
Journal title :
Macromolecules
ISSN :
0024-9297
eISSN :
1520-5835
Publisher :
Amer Chemical Soc, Washington, United States - Washington
Volume :
30
Issue :
3
Pages :
406-409
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
Available on ORBi :
since 21 January 2009

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