Chinese Journal of Polymer Science

, Volume 31, Issue 2, pp 251–262 | Cite as

Self-healing biodegradable poly(urea-urethane) elastomers based on hydrogen bonding interactions

  • Cong-cong Liu
  • Ai-ying Zhang
  • Lin Ye
  • Zeng-guo Feng (冯增国)
Paper

Abstract

Self-healing poly(urea-urethane)s (PUUs) showing a tolerance to mechanical damage are particularly desirable for high-performance elastomeric biomaterials. In this study a kind of biodegradable PUUs was synthesized from poly(ɛ-caprolactone) diol with L-lysine ethyl ester diisocyanate (LDI) extended with L-lysine ethyl ester dihydrochloride (LEED) in DMF and characterized by using 1H-NMR, FTIR, DSC, XRD, SEM and tensile tests. Interestingly, they exhibited a self-healing characteristic upon exposure to 37°C for as short as 30 min with the tensile strength keeping at 4.23 MPa and the elongation at break reaching to 627%. It is revealed that increasing the hard segment content in PUUs benefits the self-healing performance, and on the opposite increasing the soft segment content contributes to the biodegradability.

Keywords

L-lysine ethyl ester diisocyanate Poly(ɛ-caprolactone) diol Poly(urea-urethane) Self-healing Biodegradable 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Zwaag, S.V.D., J. Soft Matter, 2008, 4: 400CrossRefGoogle Scholar
  2. 2.
    Kessler, M.R., Proc. J. Inst. Mech. Eng., 2007, 221:479CrossRefGoogle Scholar
  3. 3.
    Kessler, M.R., Sottos, N.R. and White, S.R., J. Compos. A-Appl. Sci. Manufacturing, 2003, 34: 743CrossRefGoogle Scholar
  4. 4.
    White, S. R., Sottos, N.R., Geubelle, P.H., Moore, J.S., Kessler, M.R., Sriram, S.R., Brown, E.N. and Viswanathan, S., Nature, 2001, 409(6822): 794CrossRefGoogle Scholar
  5. 5.
    Dry, C. and Mcmillan, W., J. Smar. Mate. & Stru., 1996, 5(3): 297CrossRefGoogle Scholar
  6. 6.
    Kim, V.T., Nele, D.B. and Denis, V.L., Cem. Concr. Compos., 2011, 33(4): 497CrossRefGoogle Scholar
  7. 7.
    Yang, Z.X., Hollar, J. and He, X.D., J. Cem. Concr. Compos., 2011, 33(4): 506CrossRefGoogle Scholar
  8. 8.
    Ratner, B.D., J. Polym. Int., 2007, 56: 1183CrossRefGoogle Scholar
  9. 9.
    Blaiszik, B.J., Caruso, M.M., McIlroy, D.A., Moore, J.S., White, S.R. and Sottos, N.R., Polymer, 2009, 50(4): 990CrossRefGoogle Scholar
  10. 10.
    Lee, J.K., Hong, S.J. and Liu, X., J. Macromol. Res., 2004, 12: 478CrossRefGoogle Scholar
  11. 11.
    Kirkby, E.L., Michaud, V.J., Sottos, N.R., Manson, J.A.E. and White, S.R., Polymer, 2009, 50(23): 5533CrossRefGoogle Scholar
  12. 12.
    Liao, L. P., Zhang, W., Xin, Y., Wang, H.M., Zhao, Y. and Li, W.J., Chinese Sci. Bull., 2011, 56(4–5): 439CrossRefGoogle Scholar
  13. 13.
    Toohey, K. S., Sottos, N.R., Lewis, J.A., Moore, J.S. and White, S.R., Nature Mater., 2007, 6(8): 581CrossRefGoogle Scholar
  14. 14.
    Lanzara, G., Yoon, Y., Liu, H., Peng, S. and Lee, W.I., J. Nanotechnology, 2009, 20: 335704CrossRefGoogle Scholar
  15. 15.
    Wu, D.Y., Meure, S. and Solomon, D., J. Prog. Polym. Sci., 2008, 33: 479CrossRefGoogle Scholar
  16. 16.
    Wilson, G.O., Moore, J.S., White, S.R., Sottos, N.R. and Andersson, H.M., Adv. Mater., 2006, 18(1): 44CrossRefGoogle Scholar
  17. 17.
    Bergman, S.D. and Wudl, F., J. Mater. Chem., 2008, 18(1): 41CrossRefGoogle Scholar
  18. 18.
    Szalai, M.L., McGrath, D.V. and Wheeler, D.R., Macromolecules, 2007, 40(4): 818CrossRefGoogle Scholar
  19. 19.
    Liu, Y.L. and Chen, Y.W., Polymer, 2006, 47(8): 2581CrossRefGoogle Scholar
  20. 20.
    Chujo, Y., Sada, K. and Saegusa, T., Macromolecules, 1990, 2(10): 2636CrossRefGoogle Scholar
  21. 21.
    Canadell, J., Goossens, H. and Klumperman, B., Macromolecules, 2011, 44: 2536CrossRefGoogle Scholar
  22. 22.
    Montarnal, D., Tournilhac, F., Hidalgo, M., Couturier, J.L. and Leibler, L.J., J. Am. Chem. Soc., 2009, 131(23): 7966CrossRefGoogle Scholar
  23. 23.
    Cordier, P., Tournilhac, F., Leibler, L.J. and Soulie-Ziakovic, C., Nature, 2008, 451(7181): 977CrossRefGoogle Scholar
  24. 24.
    Montarnal, D., Cordier, P., Soulie-Ziakovic, C., Tournilhac, F. and Leibler, L.J., J. Polym. Sci. Part A: Polym. Chem., 2008, 46(24):7925CrossRefGoogle Scholar
  25. 25.
    Burattini, S., Colquhoun, H.M., Hayes, W., Greenland, B.W. and Wade, M., Macromol. Rapid Commun., 2009, 30(6):459CrossRefGoogle Scholar
  26. 26.
    Tuncaboylu, D.C., Sari, M., Oppermann, W. and Okay, O., Macromolecules, 2011, 44(12): 4997.CrossRefGoogle Scholar
  27. 27.
    Chen, X.X., Dam, M.A. and Ono, K.J., Science, 2002, 295: 1698CrossRefGoogle Scholar
  28. 28.
    Voyiadjis, G.Z., Shojaei, A. and Li, G.Q., J. Inter. Plasticity, 2011, 27: 1025CrossRefGoogle Scholar
  29. 29.
    Ghosh, B. and Urban, M.W., Science, 2009, 323: 1458CrossRefGoogle Scholar
  30. 30.
    Prins, L.J., Reinhoudt, D.N. and Timmerman, P.J., Angew. Chem. Int. Ed., 2001, 40(13): 2382CrossRefGoogle Scholar
  31. 31.
    Erbs, P., Findeli, A., Kintz, J., Cordier, P., Hoffmann, C., Geist, M. and Balloul, J.M., Nature, 2008, 15(1): 18Google Scholar
  32. 32.
    Saad, B., Hirt, T.D. and Welti, M., J. Biomed. Mater. Res., 1997, 36: 65CrossRefGoogle Scholar
  33. 33.
    Mohammad, K.H., Kenneth, A.M. and Robson, F.S., J. Polym. Sci. A: Polym. Chem., 2006, 44: 2990CrossRefGoogle Scholar
  34. 34.
    Bruin, P., Veenstra, G.J. and Nijenhuis, A.J., Makromol. Chem. Rapid Commun., 1988, 9: 589CrossRefGoogle Scholar
  35. 35.
    Hettrich, W. and Becker, R., Polymer, 1997, 38: 2437CrossRefGoogle Scholar
  36. 36.
    Skarja, G.A. and Woodhouse, K.A., J. Biomater. Sci. Polym. Ed., 1998, 9: 271CrossRefGoogle Scholar
  37. 37.
    Lee, H.S., Wang, Y.K. and Hsu, S.L., Macromolecules, 1987, 20(9): 2089CrossRefGoogle Scholar
  38. 38.
    Luo, N., Wang, D.N. and Ying, S.K., Polymer, 1996, 37(14): 3045CrossRefGoogle Scholar
  39. 39.
    Luo, N., Wang, D.N. and Ying, S.K., Macromolecules, 1995, 30(15): 4405CrossRefGoogle Scholar
  40. 40.
    Han, J., Cao, R.W., Chen, B., Ye, L., Zhang, A.Y., Zhang, J. and Feng, Z.G., J. Biomed. Mater. Res. A, 2011, 96(4): 705Google Scholar
  41. 41.
    Han, J., Chen, B., Ye, L., Zhang, A.Y., Zhang, J. and Feng, Z.G., J. Front Mater. Sci. China, 2009, 3(1): 25CrossRefGoogle Scholar
  42. 42.
    Bummer, P.M. and Knutson, K., Macromolecule, 1990, 23(20): 4357CrossRefGoogle Scholar
  43. 43.
    Teo, L.S., Chen, C.Y. and Kuo, J.F., Macromolecules, 1997, 30(6): 1793CrossRefGoogle Scholar
  44. 44.
    Luo, N., Wang, D.N. and Ying, S.K., Macromolecules, 1997, 30(15): 4405CrossRefGoogle Scholar
  45. 45.
    Guelcher, S.A., Gallagher, K.M. and Didier, J.E., J. Acta Biomaterialia, 2005, 1: 471CrossRefGoogle Scholar

Copyright information

© Chinese Chemical Society, Institute of Chemistry, Chinese Academy of Sciences and Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Cong-cong Liu
    • 1
  • Ai-ying Zhang
    • 1
  • Lin Ye
    • 1
  • Zeng-guo Feng (冯增国)
    • 1
  1. 1.School of Materials Science and EngineeringBeijing Institute of TechnologyBeijingChina

Personalised recommendations