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Synthesis and environmental degradation of polyesters based on poly (ε-caprolactone)

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Abstract

Poly (ε-caprolactone) (PCL), poly (δ-valerolactone) (PVL), poly (ε-caprolactone-co-δ-valerolactone) [P(CL-co-VL)], and poly (ε-caprolactone-co-ethylene oxide-co-ε-caprolactone) (PCL-PEO-PCL) were synthesized by ring-opening and diol-initiated polymerization of ε-caprolactone and δ-valerolactone. The degradation of the samples by chemical hydrolysis and in a soil burial test was evaluated. It was found that PCL, PVL, and P(CL-co-VL) degrade mainly enzymatically. The rate of degradation depends on their molecular weight, chemical structure, composition, and morphology. PCL-PEO-PCL block copolymers exhibit a repelling effect to the microorganisms in the soil, which depends on the molecular weight and relative amount of PEO block in the copolymer.

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References

  1. S. J. Huang (1990)Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 31, 54.

    Google Scholar 

  2. P. Jarrett, C. V. Benedict, J. P. Bell, J. A. Cameron, and S. J. Huang (1984) in S. W. Shalaby, A. S. Hoffman, B. D. Rather, and T. A. Horbett (Eds.),Polymers as Biomaterials, Plenum Press, New York, pp. 181–192.

    Google Scholar 

  3. J. E. Potts, R. A. Clendinning, and W. B. Ackart (1973) inThe Proceedings of Degradability of Polymers and Plastics Conference, Plastic Institute, London, pp. 10–12.

    Google Scholar 

  4. D. H. Lewis (1990) in H. Chasin and R. Langer (Eds.),Biodegradable Polymers as Drug Delivery Systems, Marcel Dekker, New York, pp. 1–43.

    Google Scholar 

  5. S. Pulapura and J. Kohn (1992)J. Biomater. Appl. 6, 216–250.

    PubMed  Google Scholar 

  6. O. Böstman (1991)J. Bone Joint Surg. 73-A, 148–153.

    Google Scholar 

  7. K. Juni and M. Nakano (1986) inCRC Critical Reviews in Therapeutic Drug Carrier Systems. CRC Press, Boca Raton, FL, Vol. 3, pp. 209–232.

    Google Scholar 

  8. R. Kavelman and B. Kendit (1978)Mycologia 70, 87–103.

    Google Scholar 

  9. R. B. Cain (1992) inMicrobial Control of Pollution, 48th Symposium of the Society for General Microbiology, University of Cardiff, Cardiff, pp. 293–338.

    Google Scholar 

  10. A. Schindler, A. R. Jeffcoat, G. L. Kimmel, C. G. Pitt, M. E. Wall, and R. A. Zweidinger (1977)Contemp. Topics Polym. Sci. 2, 251–286.

    Google Scholar 

  11. P. Wang (1989)J. Biomed. Mater. Res. 23, 91–104.

    PubMed  Google Scholar 

  12. J. E. Potts, R. A. Clendinning, and S. Cohen (1975)Soc. Plast. Eng. Tech. Pap. 21, 567–569.

    Google Scholar 

  13. F. Kawai (1987)CRC Crit. Rev. Biotechnol. 6, 273–307.

    Google Scholar 

  14. J. R. Haines and M. Alexander (1974)Appl. Microbiol. 28, 1085–1095.

    Google Scholar 

  15. D. F. Dwyer and J. M. Tiedje (1983)Appl. Environ. Microbiol. 46, 185–192.

    PubMed  Google Scholar 

  16. M. Amji and K. Park (1992)Biomaterials 13, 682–692.

    PubMed  Google Scholar 

  17. N. F. Owens, D. Gingell, and P. R. Rutter (1987).J. Cell Sci. 87, 667–675.

    PubMed  Google Scholar 

  18. N. P. Desai, S. F. A. Hossainy, and J. A. Hubbell (1992)Biomaterials 13, 417–420.

    PubMed  Google Scholar 

  19. J. D. Andrade (1973)Med. Instrum. 7, 110–121.

    PubMed  Google Scholar 

  20. G. I. Bell, M. Dembo, and P. Bongrand (1984)Biophys. J. 45, 1051–1064.

    PubMed  Google Scholar 

  21. European Community Specific Programme for Research, Technological Development and Demonstration in the Field of Agriculture and Agro-Industry, including Fisheries,Biodegradability of Bioplastics: Prenormative research, Biorecycling, and Ecological Impacts, AIR 2-CT93-1099.

  22. R. D. Lundberg, J. V. Koleske, and W. B. Wischmann (1969)J. Polym. Sci. A-1 7, 2915–2930.

    Google Scholar 

  23. R. Jérôme and Ph. Teyssié (1989) in G. Allen, J. C. Bevington, G. C. Eastmond, A. Ledwith, S. Russo, and P. Sigwalt (Eds.),Comprehensive Polymer Science, Pergamon Press, London, Vol. 3, pp. 501–510.

    Google Scholar 

  24. G. L. Brode and J. V. Koleske (1972)J. Macromol. Sci. A6, 1109–1144.

    Google Scholar 

  25. A. Schindler, J. M. Hibionada, and C. G. Pitt (1982)J. Polym. Sci. Polym. Chem. Ed. 20, 319–326.

    Google Scholar 

  26. K. Saotome and J. Kodaira (1965)Makromol. Chem. 82, 41–44.

    Google Scholar 

  27. R. F. Storey, K. R. Herring, and D. C. Hoffmann (1991)J. Polym. Sci. Part A Polym. Chem. 29, 1759–1771.

    Google Scholar 

  28. J. Loccufier, M. Van Bos, and E. Schacht (1991)Polym. Bull. 27, 201–204.

    Google Scholar 

  29. V. Crescenzi, G. Manzini, G. Calzolari, and C. Borri (1972)Eur. Polym. J. 8, 449–463.

    Google Scholar 

  30. P. Cerrai, M. Tricoli, and F. Andruzzi (1989)Polymer 30, 338–343.

    Google Scholar 

  31. W. J. Cook, J. A. Cameron, J. P. Bell, and S. J. Huang (1981)J. Polym. Sci. Polym. Lett. Ed. 19, 159–165.

    Google Scholar 

  32. H. J. Lee, J. Lopecek, and J. D. Andrade (1989)J. Biomed. Mater. Res. 23, 351–368.

    PubMed  Google Scholar 

  33. S. Nagaoka, J. Mori, H. Takiuchi, J. Jokota, H. Tanzawa, and S. Nishiumi (1984) in S. W. Shalby, A. S. Hoffmann, B. D. Ratner, and T. A. Horbett (Eds.),Polymers as Biomaterials, Plenum Press, New York, pp. 361–374.

    Google Scholar 

  34. D. Knoll and J. Hermans (1983)J. Biol. Chem. 258, 5710–5715.

    PubMed  Google Scholar 

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Authors and Affiliations

  1. Biomaterial & Polymer Research Group, Department of Organic Chemistry, University of Ghent, Krijgslaan 281 (S-4), B-9000, Ghent, Belgium

    Veska Toncheva, An Van Den Bulcke & Etienne Schacht

  2. Laboratory of Microbiology, Department of Biochemistry, Physiology and Microbiology, University of Ghent, K. L. Ledeganckstraat 35, B-9000, Ghent, Belgium

    Joris Mergaert & Jean Swings

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  1. Veska Toncheva
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  2. An Van Den Bulcke
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  3. Etienne Schacht
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  4. Joris Mergaert
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  5. Jean Swings
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Toncheva, V., Van Den Bulcke, A., Schacht, E. et al. Synthesis and environmental degradation of polyesters based on poly (ε-caprolactone). J Environ Polym Degr 4, 71–83 (1996). https://doi.org/10.1007/BF02074868

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