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Macromolecular engineering of polylactones and polylactides

I. End-functionalization of poly ɛ- caprolactone

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Summary

Aluminum alkoxides carrying functional alkoxy groups are effective initiators for theɛ-caprolactone polymerization in toluene and tetrahydrofuran. The coordination-insertion type of polymerization is living and yields exclusively linear polyesters of a predictable molecular weight with a narrow molecular weight distribution within the period of time required for the total monomer conversion. The functional group associated to the active alkoxy group of the initiator is selectively attached to one chain-end, and the second end-group is systematically a hydroxyl function resulting from the hydrolysis of the living growing site. Asymmetric telechelic polyesters are thus obtained in a perfectly controlled way, including macromonomers. Beside (meth)acrylic double bond, the functional end-group derived from the initiator can be, for instance, an unsaturation, a halogen and a tert-amine. Coupling the asymmetric telechelic polymer via the OH end-group (or the precursor Al alkoxide end-group) is a direct way to the related symmetric telechelic of a twofold increased molecular weight.

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References

  1. PITT, C.G., MARKS, T.A., SCHINDLER, A., “Biodegradable Drug Delivery Systems based on aliphatic Polyesters: Applications to Contraceptives and narcotic antagonists”, Controlled Release of Bioactive Materials, Ed. by R. Baker, Academic Press (1980)

  2. SCHINDLER, A., JEFFCOAT, R., KIMMEL, G.L., PITT, C.G., WALL, M.E. and ZWEIDINGER, R., “Biodegradable Polymer for sustained Drug Delivery”, Contemp. top. in Polymer Sci., Vol. 2, p. 251, Plenum Press (1977)

  3. BRODE, C.L., KOLESKE, J.V., J. Macromol. Sci. — Chem. A6, 1109 (1972)

    Google Scholar 

  4. COX, E.F., HOSTETTLER, F., Union Carbide Corp., U.S. Pat. 3 021 309 (1962)

  5. LUNDBERG, R.D., COX, E.F., “Ring Opening Polymerization”; Frisch, K.C., Reegen, S.L., Eds.; Dekker M.: New York; p. 247 (1969)

    Google Scholar 

  6. ITO, K., HASHIZUKA, Y. and YAMASHITA, Y., Macromolecules,10 (4), 821 (1977)

    Google Scholar 

  7. KRICHELDORF, H.R., BERL, M. and SCHARNAGL, N., Macromolecules,21, 286 (1988)

    Google Scholar 

  8. KRICHELDORF, H.R., MANG, T. and JONTE, J.M., Macromolecules,17, 2173 (1984)

    Google Scholar 

  9. ITO, K., YAMASHITA, Y., Macromolecules,11, 68 (1978)

    Google Scholar 

  10. JEROME, R. and TEYSSIE, Ph., “Comprehensive Polymer Science”, G.C. Eastmond, A. Ledwith, S. Russo and P. Sigwalt, Eds, Pergamon Press, Vol. 3, Part I, 501 (1989)

  11. SOSNOWSKI, S., SLOMKOWSKI, S, PENCZEK, S, and REIBEL, L., Makromol. Chem.,184, 2159 (1983)

    Google Scholar 

  12. OUHADI, T., STEVENS, C. and TEYSSIE, Ph., Makromol. Chem., Suppl. 1, 191 (1975)

  13. HAMITOU, A., JEROME, R. and TEYSSIE, Ph., J. Polym. Sci., Polym. Chem. Ed.,15, 865 (1977)

    Google Scholar 

  14. OUHADI, T., HAMITOU, A., JEROME, R. and TEYSSIE, Ph., Macromolecules,6, 651 (1973)

    Google Scholar 

  15. OUHADI, T., HAMITOU, A., JEROME, R. and TEYSSIE, Ph., Macromolecules,9, 927 (1976)

    Google Scholar 

  16. YASUDA, Y., AIDA, T. and INOUE, S., Macromolecules,17, 2217 (1984)

    Google Scholar 

  17. ENCO, M., AIDA, T. and INOUE, S., Macromolecules,20, 2982 (1987)

    Google Scholar 

  18. HOFMAN, A., SLOMKOWSKI, S., and PENCZEK, S., Makromol. Chem., Rapid Commun.,8, 387 (1987)

    Google Scholar 

  19. HEUSCHEN, J., JEROME, R. and TEYSSIE, Ph., Macromolecules,14, 242 (1981)

    Google Scholar 

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The authors are indebted to IRSIA for a fellowship to one of them (Ph. Dubois) and to the “Services de la Programmation de la Politique Scientifique” for financial support. NMR spectra were recorded at the CREMAN facility of the University of Liège which has been funded by a grant from the “Fonds National de la Recherche Scientifique”. The helpful assistance of Dr. Warin has been very much appreciated. They are very greatful to G. Broze (Colgate Palmolive) who initiated this research.

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Dubois, P., Jerome, R. & Teyssie, P. Macromolecular engineering of polylactones and polylactides. Polymer Bulletin 22, 475–482 (1989). https://doi.org/10.1007/BF00718922

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