Zastosowanie kationowej polimeryzacji według mechanizmu aktywowanego monomeru oraz reakcji typu „click” do syntezy funkcjonalizowanego polilaktydu

M. Bednarek

Published : 2012-08-30

Vol. 57 No. 7-8 (2012)

Application of cationic polymerization by activated monomer mechanism and click reactions for the synthesis of functionalized polylactide

M. Bednarek

Abstract

Polylactide (PLA) functionalized at one chain end with propargyl group (Propargyl-PLA, Fig. 1, 2) was synthesized using ring-opening polymerization in the presence of protic acid and alcohol, proceeding via activated monomer mechanism. The synthetic conditions were chosen so as to obtain the polymer with a predetermined molecular weight and to exclude transesterification and racemization reactions during the polymerization process (Table 2, Fig. 3). Polylactide functionalized with propargyl group was subjected to click reactions with the compounds containing azide (Fig. 4) and thiol groups. In the case of azide addition the possibility of formation of block copolymers, with an example of the coupling of Propargyl-PLA to poly(ethylene glycol) bearing -N3 group at one chain end (Fig. 5), was shown. The reactivity of terminal alkine group of Propargyl-PLA was also proved in the „thiol-yne” reaction, with a-toluenethiol (Fig. 6).

Keywords

polimeryzacja z otwarciem pierścienia ; polimeryzacja kationowa ; polilaktyd ; funkcjonalizacja ; reakcja „click” ring opening polymerization ; cationic polymerization ; polylactide ; functionalization ; click reaction

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Bednarek, M. (2012). Application of cationic polymerization by activated monomer mechanism and click reactions for the synthesis of functionalized polylactide. Polimery, 57(7-8), 501-509. Retrieved from https://ichp.vot.pl/index.php/p/article/view/846

References

Vancaeter P., Goethals E. J.: Trends Polym. Sci. 1995, 3, 227.

2. Hawker C. J., Wooley K. L.: Science 2005, 309, 1 200.

3. Williams C. K.: Chem. Soc. Rev. 2007, 36, 1 573.

4. Lecomte P., Riva R., Jérôme C., Jérôme R.: Macromol. Rapid. Commun. 2008, 12/13, 982.

5. Bednarek M.: Polimery 2006, 51, 727.

6. Rostovtsev V. V., Green L. G., Fokin V. V., Sharpless K. B.: Angew. Chem. Int. Ed. 2002, 41, 2 596.

7. Hoyle C. E., Lee T. Y., Roper T.: J. Polym. Sci. Part A: Polym. Chem. 2004, 42, 5 301.

8. Qiu S., Gao S., Lin Z., Chen G.: Progress in Chemistry 2011, 23, 637.

9. Fournier D., Hoogenboom R., Schubert U. S.: Chem. Soc. Rev. 2007, 36, 1 369.

10. Binder W. H., Sachsenhofer R.: Macromol. Rapid Commun. 2008, 29, 952.

11. Johnson J. A., Finn M. G., Koberstein J. T., Turro N. J.: Macromol. Rapid Commun. 2008, 29, 1 052.

12. Mansfeld U., Pietsch C., Hoogenboom R., Becer C. R., Schubert U. S.: Polym. Chem. 2010, 1, 1 560.

13. Tasdelen M. A.: Polym. Chem. 2011, 2, 2 133.

14. Lowe A. B.: Polym. Chem. 2010, 1, 17.

15. Kade M., Burke D., Hawker C. J.: J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 743.

16. Barakat I., Dubois P., Jérôme R, Teyssie P., Goethals E.: J. Polym. Sci.: Part A: Polym. Chem. 1994, 32, 2 099.

17. San Roman J.: Polymer 1995, 36, 173.

18. Huang S. J., Onayari J. M.: J. Macromol. Sci., Pure Appl. Chem. 1996, 33, 571.

19. Liu X., Li K., Feng X., Cao Y.: J. Macromol. Sci., Pure Appl. Chem. 2009, 46, 937.

20. Vora A., Singh K., Webster D. C.: Polymer 2009, 50, 2 768.

21. Duda A., Penczek S.: „Biopolymers”, tom 3b „Polyesters II — Properties and Chemical Synthesis” Steinbûchel (red. Doi Y.), Viley-VCH:Weinheim 2002, rozdz. 12, str. 371.

22. Mercerreyes D., Jerome R., Dubois P.: Adv. Polym. Sci. 1998, 147, 1.

23. Platel R. H., Hodgson L. M., Williams C. K.: Polym. Rev. 2008, 48, 11.

24. Kamber N. E., Jeong W., Waymouth R. M. i in.: Chem. Rev. 2007, 107, 5 813.

25. Coulembier O., Lohmeijer B. G., Dove A. P. i in.: Macromolecules 2006, 39, 5 617.

26. Jensen T. R., Schaller C. P., Hillmyer M. A. i in.: J. Organomet. Chem. 2005, 690, 5 881.

27. Kricheldorf H. R., Kreiser I. R.: Makromol. Chem. 1987, 188, 1 861.

28. Rangel I., Ricard M., Ricard A.: Macromol. Chem. Phys. 1994, 195, 3 095.

29. Bourissou D., Martin-Vaca B., Dumitrescu A., Graullier M., Lacombe F.: Macromolecules 2005, 38, 9 993.

30. Baoeko M., Kubisa P.: J. Polym. Sci. Part A: Polym. Chem. 2007, 45, 3 090.

31. Baoeko M., Kubisa P.: J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 7 919.

32. Baoeko M., Kubisa P.: J. Polym. Sci. Part A: Polym. Chem. 2010, 48, 2 650.

33. Kubisa P., Penczek S.: Prog. Polym. Sci. 1999, 24, 1 409.

34. Penczek S., Cypryk M., Duda A., Kubisa P., Słomkowski S.: Prog. Polym. Sci. 2007, 32, 247.

35. Bednarek M., Baoeko M.: React. Funct. Polym., 2012, 72, 213.

36. Billiet L., Fournier D., Du Prez F.: J. Polym. Sci. Part A: Polym. Chem. 2008, 46, 6 552.

37. Tsui H., Ykada Y., Hyon S. H., Kimura Y., Kitao T.: J. Appl. Polym. Sci. 1994, 51, 337.

38. Tonelli A. E., Flory P. J.: Macromolecules 1969, 2, 225.

39. Kowalski A., Duda A., Penczek S.: Macromolecules 1998, 31, 2114.

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