Cykliczne węglany w syntezie polimerów biodegradowalnych

A. Plichta; Z. Florjańczyk; G. Rokicki

Published : 2022-09-01

Vol. 50 No. 7-8 (2005)

Cyclic carbonates in the synthesis of biodegradable polymers

A. Plichta Z. Florjańczyk G. Rokicki

Abstract

In the literature review most important results of studies on biodegradability of aliphatic polycarbonates and copolymers of cyclic carbonates (ethylene carbonate or trimethylene carbonate) with heterocyclic monomers have been presented. A new idea about mechanism of poly(ethylene carbonate) degradation in vivo in the presence of peroxide anion-radical initiating the chain depolymerization leading to ethylene carbonate and further to CO2 and ethylene glycol [equation (4)] has been discussed. In the part concerning authors' research the results of homopolymerization of various heterocyclic monomers [among others propylene oxide (POX), ethylene carbonate (EC), trimethylene carbonate (TMC), L-lactide (L-LA)] catalyzed with methylaluminoxane (MAO) (Table 1) were presented. The polymers were investigated using 1H NMR (Fig. 1), 13C NMR (Fig. 2) and MALDI TOF (Figs. 3, 4) methods. It was demonstrated that in the presence of MAO the products showing the linear as well as cyclic structures were formed. Formation of macrocyclic oligomers shows the presence of some electrophilic centers in MAO structure, which lead to the reaction of back-bitting type. L-lactide and racemic lactide were copolymerized with EC or terpolymerized with EC and POX in the presence of various catalysts (MAO, MAO modified with ZnEt2, Et2AlOEt - Table 2). The products obtained contained up to 6.5 % of carbonate units maximally. L-LA/EC copolymer with the highest content (6.5 wt. %) of carbonate mers was obtained in the presence of MAO modified with ZnEt2.

Keywords

monomery heterocykliczne ; polimeryzacja ; metyloalumoksan ; węglan etylenu ; kopolimery laktydowo-węglanowe ; zawartość merów węglanowych heterocyclic monomers ; polymerization ; methylaluminoxane ; ethylene carbonate ; lactide - carbonate copolymers ; content of carbonate mers

Details

References

Statistics

Authors

Download files

PDF (Język Polski)

Zasady cytowania

Plichta, A., Florjańczyk, Z., & Rokicki, G. (2022). Cyclic carbonates in the synthesis of biodegradable polymers. Polimery, 50(7-8), 537-545. Retrieved from https://ichp.vot.pl/index.php/p/article/view/1661

References

Carothers W. H., Van Natta F. J.: J. Am. Chem. Soc. 1930,52,314.

2. Carothers W. H., Dorough G. L., Van Natta F. J.: Am. Chem. Soc. 1932,54,761.

3. Kricheldorf H. R, Jenssen J., Kreiser-Sanders 1.: Macramol. Chem. 1991,192,2391.

4. Penco M., Donetti R, Mendichi R, Ferruti P.: Macrmol. Chem. Phys. 1998,199,1737.

5. Rokicki G.: Prago Palym. Sci. 2000,25,259.

6. Vogdanis L., Martens B., Uchtmann H., Henzel F., Heitz w.: Makromol. Chem. 1990,191,465.

7. Soga K, Hosoda S., Tazuke Y., Ikeda S.: J. Polym. Sci Part A: Palym. Chem. 1977,15,219.

8. Inoue S., Koinuma H., Tsuruta T.: Makromol. Chem. 1969,130,210.

9. Inoue S., Koinuma H., Yokoo Y., Tsuruta T.: Makrmol. Chem. 1971,143,97.

10. Rokicki A., Kuran w.: Makromol. Chem. 1979, 180 2153.

11. Duda A., Penczek S.: Polimery 2003, 48, 16.

12. Duda A.: Polimery 2004, 49, 469.

13. Nishida H., Tokiwa Y.: Chem. Lett. 1994,421.

14. Zhu K J., Hendren R W., Jensen K, Pit C G.: Macromalecules 1991,24,1736.

15. Albertsson A.-C, Eklund S.: J. Appl. Polym. Sci. 1995 57,87.

16. Hori Y., Gonda Y., Takahashi Y., Hagiwara T.: Macromolecules 1996,29,804.

17. Imada Y., Kajikawa Y., Taniguchi M., Masuda T.: Kobunshi Robunshu 1999,56,109.

18. Yasuda H., Aludin M.-S., Kitamura N., Tanabe M.I, Sirahama H.: Macromalecules 1999,32,6047.

19. Takanashi M., Nomura Y., Yoshida Y., Inoue S.: Makramol. Chem. 1982, 183,2085.

20. Kawaguchi T., Nakano M., [uni K, Inoue S., Yoshida Y.: Chem. Pharm. Bull. 1983,31,1400.

21. Zhou M., Takayanagi M., Yoshida Y., Ishii S., Noguchi H.: Polym. BulI. 1999,42,419.

22, Imai Y., Kojima K, Watanabe A, Masuhara E.: Jinko Zoki 1974, 3, 212.

23. Acemoglu M.: Int. J. Pharm. 2004,277, 133.

24. Acemoglu M., NimmerfalI F., Bantle S., StolI H.: J. Control. Release 1997, 49, 263.

25. StolI G. H., NimmerfalI F., Acemoglu M., Bodmer D., Bantle S., Muller L, Mahl A, Kolopp M., Tullberg K: f. Control. Release 2001, 76, 209.

26. Dadsetan M., Christenson E. M., Unger F., Ausborn M., Kissel T., Hiltner A, Anderson J. M.: J. Control. Release 2003,93,259.

27. Kuran w., Listo T.: Makromol. Chem. 1992,193,945.

28. Kuran w., Listo T.: Polimery 1993, 38, 366.

29. Kuran w., Listo T., Iwaniuk K, Rokicki G.: Polimery 1993,38,405.

30. Rokicki G., Nguyen X. T.: Macromol. Reports 1995, A32,265.

31. Pat. USA 424457 (1954).

32. Hoecker H., Keul H.: Macromol. Symp. 2000, 157, 71.

33. Ubaghs L., Novi c., Keul H., Hoecker H.: Macromol. Chem. Phys. 2004, 205, 888.

34. Ubaghs L., Waringo M., Keul H., Hoecker H.: Macromolecules 2004, 37, 6755.

35. Evans W. J., Katsumata H.: Macromolecules 1994,27, 4011.

36. Shirahama H., Kanetani A, Yasuda H.: Polymer J. 2000,32,280.

37. Agarwal S., Naumann N., Xie X. L.: Macromolecules 2002, 35, 7713.

38. Penczek S., Kubisa P., Matyjaszewski K: Adv. Polym. Sci. 1980, 37,

39. Montaudo G., Montaudo M. S., Puglisi c., Samperi F., Spassky N., LeBorgne A, Wisniewski M.: Macromolecules 1996,29,6461.

40. Duda A, Penczek S.: Macromolecules 1990, 23, 1636.

41. Duda A, Penczek S.: Macromolecules 1994,27,4867.

Google Scholar

Citing articles via

Statistics

Total abstract views : 58

PDF Downloads : 93

A. Plichta aplichta@ch.pw.edu.pl

Affiliation
Politechnika Warszawska, Wydział Chemiczny, ul. Noakowskiego 3, 00-664 Warszawa

Z. Florjańczyk

Affiliation
Politechnika Warszawska, Wydział Chemiczny, ul. Noakowskiego 3, 00-664 Warszawa

G. Rokicki

Affiliation
Politechnika Warszawska, Wydział Chemiczny, ul. Noakowskiego 3, 00-664 Warszawa