[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/Unit :
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
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Quirk, R. P.; Zhu, L. Br Polym J 1990, 23, 47.
Charlier, P.; Jérôme, R.; Teyssié, P. Macromolecules 1990, 23, 1831.
Stewart, M. J.; Shepherd, N.; Service, D. Br Polym J 1990, 22, 319.
Schulz, D. N.; Halasa, A. F. J Polym Sei Polym Chem Ed 1977, 15, 2401.
Cernohous, J. J.; Macosko, C. W.; Hoye, T. R. Macromolecules 1998, 31, 3759.
Vanden Eynde, X.; Poleunis, C.; Bertrand, P.; Fallais, I.; Devaux, J. Proc. 2nd International Conference, Polymer-Solid Interfaces: From Model To Real Systems, Namur, Belgium, August 12-16, 1996, Presses Universitaires de Namur, 1998, p 473.
Safarik, L.; Stranski, Z. In Titrimetric Analysis In Organic Solvents; Svehla, G., Ed.; Comprehensive Analytical Chemistry, Vol. XXII; Elsevier Science Publisher: Amsterdam, 1986.
Morton, M. In Anionic Polymerization: Principles and Practice; Academic Press: New York, 1983.
Young, R. N.; Quirk, R. P.; Fetters, L. J. Adv Polym Sci 1984, 56, 1.
Gonsalves, K.; Rausch, M. D. J Polym Sci Polym Chem Ed 1986, 24, 1419.
March, J. In Advanced Organic Chemistry, 4th ed.; Wiley Interscience: New York, 1992; Chapter 10, p 498.
Quirk, R. P.; Lynch, T. Macromolecules 1993, 26, 1206.
Newman, J. G.; Carlson, B. A.; Michael, R. S.; Moulder, J. F. In Static SIMS Handbook of Polymer Analysis; Hohlt, T. A., Ed.; Perkin-Elmer Corporation: Eden Prairie, Minnesota, 1991; p 26.
Briggs, D.; Brown, A.; Vickerman, J. C. In Handbook of Static Secondary Ion Mass Spectrometry (SIMS); Wiley Interscience: New York, 1989.
Bellamy, L. J. In the Infra Red Spectra of Complex Molecules, 2nd ed.; Chapman & Hall: London, 1980; Vol. 2, Chapter 7, p 221.
Gust, J. E. In the Chemistry of Azido Group; Patai, S., Ed.; Interscience Publishers: London, 1971; Chapter 3, p 195.
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).
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.