[en] This paper reports on the synthesis of a novel poly(ethylene oxide) (PEO) macromonomer, which can be copolymerized with epsilon-caprolactone (epsilon-CL) by ring-opening polymerization (ROP). PEO chains end-capped by an epsilon-caprolactone unit (gammaPEO(.)CL) have been synthesized by living anionic ring-opening polymerization of ethylene oxide (EO) initiated by the potassium alkoxide of 1,4-dioxaspiro[4.5]decan-8-ol, followed by derivatization of the acetal into a ketone and the Baeyer-Villiger oxidation of the ketone into a lactone. The end-capping of PEO by epsilon-CL was assessed by FTIR, MALDI-TOF, and H-1 NMR spectroscopy. This type of macromonomer is a precursor of amphiphilic comblike copolymers consisting of a biodegradable hydrophobic backbone of poly-(epsilon-caprolactone) (PCL) and hydrophilic PEO grafts. Copolymerization of gammaPEO(.)CL with epsilon-CL was successfully initiated by aluminum alkoxide.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Rieger, Jutta ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Bernaerts, Katrien V.; Ghent University > Department of Organic Chemistry
Du Prez, Filip E; Ghent University > Department of Organic Chemistry
Jérôme, Robert ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Lactone end-capped poly(ethylene oxide) as a new building block for biomaterials
Publication date :
28 December 2004
Journal title :
Macromolecules
ISSN :
0024-9297
eISSN :
1520-5835
Publisher :
Amer Chemical Soc, Washington, United States - Washington
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
Lee, J. H.; Lee H. B.; Andrade, J. D. Prog. Polym. Sci. 1998, 20, 1043-1079.
Vermette, P.; Meagher, L. Colloids Surf., B 2003, 28, 153-198.
Gref, R.; Lück, M.; Quellec, P.; Marchand, M.; Dellacherie, E.; Harnisch, S.; Blunck, T.; Müller, R. H. Colloids Surf. B 2000, 18, 301-313.
Peracchia, M. T.; Vauthier, C.; Passirani, C.; Couvreur, P.; Labarre, D. Life Sciences 1997, 61, 749-761.
Lee, J. H.; Kopeckova, P.; Kopecek, J.; Andrade, J. D. Biomaterials 1990, 11, 455-464.
Walton, D. G.; Soo, P. P.; Mayes, A. M.; Sofia-Allgor, S. J.; Fujii, J. T.; Griffith, L. G.; Ankner, J. F.; Kaiser, H.; Johansaon, J.; Smith, G. D.; Barker, J. G.; Satjja, S. K. Macromolecules 1997, 30, 6947-6956.
Gref, R.; Minamitake, Y.; Peracchia, M. T.; Trubetskoy, V.; Torchilin, V.; Langer, R. Science 1994, 263, 1600-1603.
Nucci, M. L.; Shorr, R.; Abuchowski, A. Adv. Drug Deliv. Rev 1991, 6, 133-151.
Delgado, C.; Francis, G. E.; Fisher, D. Crit. Rev. Ther. Drug Carrier Syst. 1992, 9, 249-304.
Ould-Ouali, L.; Arien, A.; Rosenblatt, J.; Nathan, A.; Twaddle, P.; Matalenas, T.; Borgia, M.; Arnold, S.; Leroy, D.; Dinguizli, M.; Rouxhet, L.; Brewster, M.; Préat, V. Pharm. Res. 2004, 21, 1581-1590.
Harris, J. M., Ed. Poly(ethylene glycol) chemistry: Biotechnical and Biomedical Applications; Plenum Press: New York, 1992.
Irvine, D. J.; Mayes, A. M.; Griffith, L. G. Biomacromolecules 2001, 2, 85-94.
Irvine, D. J.; Ruzette, A.-V. G.; Mayes, A. M.; Griffith, L. G. Biomacromolecules 2001, 2, 545-556.
Toncheva, V.; Wolfert, M. A.; Dash, P. R.; Oupicky, D.; Ulbrich, K.; Seymour, L. W.; Schacht, E. H. Biochim. Biophys. Acta 1998, 1380, 354-368.
Vandorpe, J.; Schacht, E.; Stolnik, S.; Garnett, M. C.; Davies, M. C.; Illum, L.; Davis, S. S. Biotechnol. Bioeng. 1996, 52, 89-95.
Kwon, G.; Suwa, S.; Yokoyama, M.; Okano, T.; Sakurai, Y.; Kataoka, K J. Controlled Release 1994, 29, 17-23.
Twaik, M. A.; Tahan, M.; Zilkha, A. J. Polym. Sci., Part A: Polym. Chem. 1969, 7, 2469-2480.
Thierry, A.; Skoulios, A. Makromol. Chem. 1976, 177, 319-335.
Wesslen, B.; Wesslen, K. B. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 3915-3926.
Jannasch, P.; Wesslen, B. J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 1519-1529.
Jannasch, P.; Wesslen, B. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 1465-1474.
Bo, G.; Wesslen, B.; Wesslen, K. B. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 1799-1808.
Lee, J. H.; Kopeckova, P.; Zhang, J.; Kopecek, J.; Andrade, J. D. Polym. Mater. Sci. Eng. 1988, 59, 234-238.
