Skip to main content
SpringerLink
Log in

Enhanced Thermal Stability of Polylactide by Terminal Conjugation Groups

  • Published:
Journal of Electronic Materials Aims and scope Submit manuscript

Abstract

Various acids such as aliphatic or carbocyclic fatty or aromatic acids were successfully conjugated into the ending hydroxyl group of poly(l-lactide) (PLLA). The chemical structures of various acid–PLLAs were confirmed by Fourier transform infrared and proton nuclear magnetic resonance analysis. The crystallinity and solubility of the original PLLA were maintained after the terminal conjugation of various acids. The thermal properties were significantly improved, especially the 10% weight-loss temperature that showed an increase of over 80°C for conjugation of aliphatic or aromatic acids as compared to that of the corresponding original PLLA. In addition, more than 60 wt.% of the aliphatic acid–PLLAs was pyrolyzed, and aromatic acid–PLLAs degraded only about 10 wt.% for 150 min, although the original PLLA was pyrolyzed completely at 250°C for 7 min. The thermal stability of PLLA was controlled by the conjugation of aliphatic or aromatic acids into a chain end. These acid–PLLAs may be useful as materials with high thermal stability for various application fields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. P.U. Rokkanen, O. Blostman, E. Hirvensalo, E.A. Makela, E.K. Partio, H. Patiala, S. Vainionpaa, K. Vihtonen, and P. Tormala, Biomaterials 21, 2607 (2000).

    Article  Google Scholar 

  2. R. Auras, B. Harte, and S. Selke, Macromol. Biosci. 4, 835 (2004).

    Article  Google Scholar 

  3. J.M. Becker, R.J. Pounder, and A.P. Dove, Macromol. Rapid Commun. 31, 1923 (2010).

    Article  Google Scholar 

  4. N. Ogata, G. Jimenez, H. Kawai, and T. Ogihara, J. Polym. Sci. B 35, 389 (1997).

    Article  Google Scholar 

  5. Y. Zhao, X. Shuai, C. Chen, and F. Xi, Chem. Mater. 15, 2836 (2003).

    Article  Google Scholar 

  6. Y. Chen, R. Wombacher, J.H. Wendorff, J. Visjager, P. Smith, and A. Greiner, Biomacromolecules 4, 974 (2003).

    Article  Google Scholar 

  7. M. Nagata and Y. Sato, Polym. Int. 54, 386 (2005).

    Article  Google Scholar 

  8. M. Matsusaki, A. Kishida, N. Stainton, C.W.G. Ansell, and M. Akashi, J. Appl. Polym. Sci. 82, 2357 (2001).

    Article  Google Scholar 

  9. F. Carrasco, P. Pages, J. Gamez-Perez, O.O. Santana, and M.L. Maspoch, Polym. Degrad. Stab. 95, 116 (2010).

    Article  Google Scholar 

  10. M. Kumar, S. Mohanty, S.K. Nayak, and M. Rahail Parvaiz, Bioresour. Technol. 101, 8406 (2010).

    Article  Google Scholar 

  11. Y. Liu, D. Peng, K. Huang, S. Liu, and Z. Liu, Polym. Degrad. Stab. 95, 2453 (2010).

    Article  Google Scholar 

  12. H. Nishida, T. Mori, S. Hoshihara, Y. Fan, Y. Shirai, and T. Endo, Polym. Degrad. Stab. 81, 515 (2003).

    Article  Google Scholar 

  13. Y. Fan, H. Nishida, Y. Shirai, and T. Endo, Polym. Degrad. Stab. 84, 143 (2004).

    Article  Google Scholar 

  14. T. Mori, H. Nishida, Y. Shirai, and T. Endo, Polym. Degrad. Stab. 84, 243 (2004).

    Article  Google Scholar 

  15. H. Abe, N. Takahashi, K.J. Kim, M. Mochizuki, and Y. Doi, Biomacromolecules 5, 1480 (2004).

    Article  Google Scholar 

  16. H. Abe, N. Takahashi, K.J. Kim, M. Mochizuki, and Y. Doi, Biomacromolecules 5, 1606 (2004).

    Article  Google Scholar 

  17. F.D. Kopinke, M. Remmler, K. Mackenzie, M. Moder, and O. Wachsen, Polym. Degrad. Stab. 53, 329 (1996).

    Article  Google Scholar 

  18. H.T. Tran, M. Matsusaki, and M. Akashi, Chem. Commun. 33, 3918 (2008).

    Google Scholar 

  19. H.T. Tran, M. Matsusaki, and M. Akashi, Biomacromolecules 10, 766 (2009).

    Article  Google Scholar 

  20. H.T. Tran, M. Matsusaki, and M. Akashi, J. Polym. Sci. A 49, 3152 (2011).

    Article  Google Scholar 

  21. H. Ajiro, Y.-J. Hsiao, H.T. Tran, T. Fujiwara, and M. Akashi, Chem. Commun. 48, 8478 (2012).

    Article  Google Scholar 

  22. H. Ajiro, Y.-J. Hsiao, H.T. Tran, T. Fujiwara, and M. Akashi, Macromolecules 46, 5150 (2013).

    Article  Google Scholar 

  23. Y. Ikada, K. Jamshidi, H. Tsuji, and S.-H. Hyon, Macromolecules 20, 904 (1987).

    Article  Google Scholar 

  24. T. Kaneko, H.T. Tran, D.-J. Shi, and M. Akashi, Nat. Mater. 5, 966 (2006).

    Article  Google Scholar 

  25. H.T. Tran, M. Matsusaki, and M. Akashi, Langmuir 25, 10567 (2009).

    Article  Google Scholar 

  26. D.-J. Shi, M. Matsusaki, and M. Akashi, Bioconjugate Chem. 20, 1917 (2009).

    Article  Google Scholar 

  27. G.K. Kole, G.K. Tan, and J.J. Vittal, J. Org. Chem. 76, 7860 (2011).

    Article  Google Scholar 

  28. H. Du and J. Zhang, Sens. Actuators A 179, 114 (2012).

    Article  Google Scholar 

  29. L. Fertier, H. Koleilat, M. Stemmelen, O. Giani, C. Joly-Duhamel, V. Lapinte, and J.-J. Robin, Prog. Polym. Sci. 38, 932 (2013).

    Article  Google Scholar 

  30. V. Ramamurthy and B. Mondal, J. Photochem. Photobiol. C 23, 68 (2015).

    Article  Google Scholar 

  31. T. Bobula, J. Betak, R. Buffa, M. Moravcova, P. Klein, O. Zidek, V. Chadimova, R. Pospisil, and V. Velebny, Carbohydr. Polym. 125, 153 (2015).

    Article  Google Scholar 

Download references

Acknowledgements

We acknowledge Prof. H. Uyama of the Department of Applied Chemistry, Graduate of Engineering, Osaka University for the TGA measurements.

Author information

Authors and Affiliations

  1. Faculty of Chemical Technology, Viet Tri University of Industry, Tien Kien, Lam Thao, Phu Tho, Vietnam

    Hang Thi Tran & Ngo Dinh Vu

  2. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, 565-0871, Japan

    Michiya Matsusaki

  3. Graduate School of Frontier Biosciences, Osaka University, 1-3 Yamada-oka, Suita, 565-0871, Japan

    Mitsuru Akashi

Authors
  1. Hang Thi Tran
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michiya Matsusaki
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mitsuru Akashi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Ngo Dinh Vu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ngo Dinh Vu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tran, H.T., Matsusaki, M., Akashi, M. et al. Enhanced Thermal Stability of Polylactide by Terminal Conjugation Groups. J. Electron. Mater. 45, 2388–2394 (2016). https://doi.org/10.1007/s11664-015-4329-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11664-015-4329-9

Keywords

Search

Navigation