[en] A new and very efficient route for the synthesis of aliphatic primary amine terminated polystyrene (PS) is reported. In contrast to most known methods, only traditional commercially available reagents are used. PS is synthesized by anionic polymerization with a lithium counter ion and the living chains are end-capped by a hydroxyl group upon addition of ethylene oxide followed by protonation. The -hydroxyl end group is tosylated and the tosylate is then reacted with sodium azide. The azide terminal group is finally reduced into primary amine. The different steps of functionalization have been fully characterized by SEC, ToF-SIMS, FTIR, and 1H NMR. The amine content (= 98%) has been determined by acid-base titration with perchloric acid. It clearly shows the efficiency of the synthetic method reported in this article although it is a multistep method.
Research center :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Fallais, Isabelle; Université Catholique de Louvain (UCL) > Laboratoire de Chimie et de Physique des Hauts Polymères (POLY)
Devaux, Jacques; Université Catholique de Louvain (UCL) > Laboratoire de Chimie et de Physique des Hauts Polymeèes (POLY)
Jérôme, Robert ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
End-capping of polystyrene by aliphatic primary amine by derivatization of precursor hydroxyl end group
Publication date :
01 May 2000
Journal title :
Journal of Polymer Science. Part A, Polymer Chemistry
ISSN :
0887-624X
eISSN :
1099-0518
Publisher :
John Wiley & Sons, Hoboken, United States - New Jersey
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture [BE]
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We recently heard that the product with n = 3 and x = Cl reacted with Li, giving the corresponding protected initiator, is now commercially available (FMC Lithium Division).