[en] A straightforward strategy is proposed for grafting hydroxyl, carboxylic acid and epoxide groups along poly (epsilon-caprolactone) chains. Statistical copolymerization of epsilon-caprolactone (epsilon-CL) with alpha-chloro-epsilon-caprolactone (alpha-Cl-epsilon-CL) has been initiated by 2,2-dibutyl-2-stanna-1,3-dioxepane (DSDOP), followed by the atom transfer radical addition (ATRA) of but-3-en-1-ol, vinylacetic acid and 1,2-epoxyhex-5-ene, respectively, onto the alpha-chloro units of a poly(alpha-Cl-epsilon-CL-co-epsilon-CL) copolymer. alpha-Cl-epsilon-CL is easily prepared by the Baeyer-Villiger oxidation of 2-chlorocyclohexanone. The influence of the experimental conditions, i.e. temperature, solvent, catalyst, on the grafting yield has been discussed. Because ATRA is tolerant of the investigated functional groups, no protection/deprotection reaction is required, which is a major advantage of the method.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Riva, Raphaël ; Université de Liège - ULiège > Centre d'études et de rech. sur les macromolécules (CERM)
Lenoir, Sandrine ; Université de Liège - ULiège > Département des sciences de la vie > Biologie et génétique moléculaire
Jérôme, Robert ; Université de Liège - ULiège > Centre d'études et de rech. sur les macromolécules (CERM)
Lecomte, Philippe ; Université de Liège - ULiège > Centre d'études et de rech. sur les macromolécules (CERM)
Language :
English
Title :
Functionalization of poly(epsilon-caprolactone) by pendant hydroxyl, carboxylic acid and epoxide groups by atom transfer radical addition
Publication date :
08 September 2005
Journal title :
Polymer
ISSN :
0032-3861
eISSN :
1873-2291
Publisher :
Elsevier Sci Ltd, Oxford, United Kingdom
Special issue title :
Controlled macromolecular synthesis and controlled architectures - Supramolecular polymer assemblies
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture [BE]
Commentary :
The authors acknowledge Polymer (Elsevier) for allowing them to archive this paper.