Skip to main content
SpringerLink
Log in

Synthesis of cyclic oligo(ethylene adipate)s and their melt polymerization to poly(ethylene adipate)

  • Papers
  • Published:
Chinese Journal of Polymer Science Aims and scope Submit manuscript

Abstract

We present here the first synthesis of cyclic oligo(ethylene adipate)s (COEAs) via pseudo-high dilution condensation reaction of adipoyl chloride with ethylene glycol, and the synthesis of corresponding poly(ethylene adipate) (PEA) via the melt polymerization of COEAs. The structure of COEAs was characterized and proved by 1H-NMR and MALDI-TOF mass measurements. The effects of organic base, reaction temperature and the ratio of adipoyl chloride to ethylene glycol on the yield of COEAs were studied, and the optimum reaction condition was revealed. PEA, a diacid and diol based semi-crystalline green aliphatic polyester, was synthesized by the melt polymerization of COEAs using Ti(n-C4H9O)4 as catalyst and 1,10-decanediol as initiator at 200 °C, which follows the polycondensation-coupling ring-opening polymerization method. Our strategy should be applicable to the synthesis of versatile aliphatic polyesters based on diacid and diol monomers, which have potential applications as biocompatible and biodegradable materials.

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. Bari, S.S., Chatterjee, A. and Mishra, S., Polym. Rev., 2016, 56(2): 287

    Article  CAS  Google Scholar 

  2. Lu, L., Yaszemski, M.J. and Mikos, A.G., Biomaterials, 2001, 22(24): 3345

    Article  CAS  Google Scholar 

  3. Lim, S.T., Hyun, Y.H., Choi, H.J. and Jhon, M.S., Chem. Mater., 2002, 14(4): 1839

    Article  CAS  Google Scholar 

  4. Surnar, B. and Jayakannan, M., Biomacromolecules, 2016, 17(12): 4075

    Article  CAS  Google Scholar 

  5. Kasuya, K.I., Takagi, K.I., Ishiwatari, S.I., Yoshida, Y. and Doi, Y., Polym. Degrad. Stab., 1998, 59(1-3): 327

    Google Scholar 

  6. He, Y.S., Zeng, J.B., Li, S.L. and Wang, Y.Z., Thermochim. Acta, 2012, 529: 80

    Article  CAS  Google Scholar 

  7. Qiu, S., Su, Z. and Qiu, Z., Ind. Eng. Chem. Res., 2016, 55(39): 10286

    Article  CAS  Google Scholar 

  8. Lv, A., Cui, Y., Du, F.S. and Li, Z.C., Macromolecules, 2016, 49(22): 8449

    Article  CAS  Google Scholar 

  9. Kuhl, N., Abend, M., Bode, S., Schubert, U.S. and Hager, M.D., J. Appl. Polym. Sci., 2016, 133(44): 44168

    Article  Google Scholar 

  10. Vandesteene, M., Jacquel, N., Saint-Loup, R., Boucard, N., Carrot, C., Rousseau, A. and Fenouillot, F., Chinese J. Polym. Sci., 2016, 34(7): 873

    Article  CAS  Google Scholar 

  11. Diaz, A., Katsarava, R. and Puiggali, J., Int. J. Mol. Sci., 2014, 15(5): 7064

    Article  CAS  Google Scholar 

  12. Zhao, J.B., Wu, X.F. and Yang, W.T., J. Appl. Polym. Sci., 2004, 92(5): 3333

    Article  CAS  Google Scholar 

  13. Huang, C.Q., Luo, S.Y., Xu, S.Y., Zhao, J.B., Jiang, S.L. and Yang, W.T., J. Appl. Polym. Sci., 2009, 115(3): 1555

    Article  Google Scholar 

  14. Xu, S.Y., Shi, Y.H., Zhao, J.B., Jiang, S.L. and Yang, W.T., Polym. Adv. Technol., 2011, 22(12): 2360

    Article  CAS  Google Scholar 

  15. Morales-Huerta, J.C., Martínez de Ilarduya, A. and Muñoz-Guerra, S., ACS Sustainable Chem. Eng., 2016, 4(9): 4965

    Article  CAS  Google Scholar 

  16. Brunelle, D.J., Bradt, J.E., Serth-Guzzo, J., Takekoshi, T., Evans, T.L., Pearce, E.J. and Wilson, P.R., Macromolecules, 1998, 31(15): 4782

    Article  CAS  Google Scholar 

  17. Youk, J.H., Kambour, R.P. and MacKnight, W.J., Macromolecules, 2000, 33(10): 3594

    Article  CAS  Google Scholar 

  18. Pepels, M.P.F., van der Sanden, F., Gubbels, E. and Duchateau, R., Macromolecules, 2016, 49(12): 4441

    Article  CAS  Google Scholar 

  19. Xu, Q.Z., Chen, J.Y., Huang, W.C., Qu, T.G., Li, X.H., Li, Y., Yang, X.M. and Tu, Y.F., Macromolecules, 2013, 48(18): 7274

    Article  Google Scholar 

  20. Chen, J.Y., Chen, D.X., Huang, W.C., Yang, X.M., Li, X.H., Tu, Y.F. and Zhu, X.L., Polymer, 2016, 107: 29

    Article  CAS  Google Scholar 

  21. Zhu, X., Gu, J.L., Li, X.H., Yang, X.M., Wang, L., Li, Y.J., Li, H. and Tu, Y.F., Polym. Chem., 2017, 8: 1953

    Article  CAS  Google Scholar 

  22. Dell’Olio, C., Leonard, S., Dao, B., Varley, R.J. and Pingkarawat, K., J. Mater. Sci., 2015, 50(24): 8073

    Article  Google Scholar 

  23. Morales-Huerta, J.C., Martínez de Ilarduya, A. and Muñoz-Guerra, S., Polymer, 2016, 87: 148

    Article  Google Scholar 

  24. Nakayama, Y., Sakaguchi, K., Tanaka, R., Cai, Z. and Shiono, T., Macromol. Symp., 2015, 350(1): 7

    Article  CAS  Google Scholar 

  25. Zhang, D., Hillmyer, M.A. and Tolman, W.B., Macromolecules, 2004, 37(22): 8198

    Article  CAS  Google Scholar 

  26. Goodman, I. and Nesbitt, B.F., Polymer, 1960, 1: 384

    Article  CAS  Google Scholar 

  27. Siriphannon, P. and Monvisade, P., Bull. Mater. Sci., 2013, 36(1): 121

    Article  CAS  Google Scholar 

  28. Monvisade, P. and Loungvanidprapa, P., Eur. Polym. J., 2007, 43(8): 3408

    Article  CAS  Google Scholar 

  29. Choi, W.J., Kim, S.H., Kim, Y.J. and Kim, S.C., Polymer, 2004, 45(17): 6045

    Article  CAS  Google Scholar 

  30. Wang, H.J., Feng, H.P., Wang, X.C., Du, Q.C. and Yan, C., Chinese J. Polym. Sci., 2015, 33(6): 823

    Article  CAS  Google Scholar 

  31. Taggi, A.E., Wack, H., Hafez, A.M., France, S. and Lectka, T., Org. Lett., 2002, 4(4): 627

    Article  CAS  Google Scholar 

  32. Paull, D.H., Weatherwax, A. and Lectka, T., Tetrahedron, 2009, 65(34): 6771

    Article  CAS  Google Scholar 

  33. Hyatt, J.A. and Raynolds, P.W., “Organic reactions”, John Wiley & Sons, 1994, p. 159

    Book  Google Scholar 

  34. Wu, J., Qu, T.G., Gao, L.F., Yang, X.M., Li, X.H., Tu, Y.F. and Zhu, X.L., Chinese J. Polym. Sci., 2015, 33(8): 1069

    Article  CAS  Google Scholar 

  35. Chen, D.X., Gao, L.F., Li, X.H. and Tu, Y.F., Chinese J. Polym. Sci., 2017, 35(5): 681

    Article  CAS  Google Scholar 

  36. Wu, H. and Qiu, Z., Ind. Eng. Chem. Res., 2012, 51(40): 13323

    Article  CAS  Google Scholar 

  37. Lugito, G. and Woo, E.M., Soft matter, 2015, 11(5): 908

    Article  CAS  Google Scholar 

  38. Rohindra, D., Kuboyama, K. and Ougizawa, T., Eur. Polym. J., 2012, 48(10): 1768

    Article  CAS  Google Scholar 

  39. Liang, R., Chen, Y.C., Zhang, C.Q., Yin, J., Liu, X.L., Wang, L.K. and Yang, J.J., Chinese J. Polym. Sci., 2017, 35(4): 558

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank Prof. Mingyu Guo at Soochow University for his kind help on the tensile strength measurements of PEA samples.

Author information

Authors and Affiliations

  1. Jiangsu Key Laboratory of Advanced Functional Polymer Design and Application, State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China

    Min Lu, Xiang Zhu, Xiao-hong Li, Xiao-ming Yang & Ying-feng Tu  (屠迎锋)

Authors
  1. Min Lu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiang Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiao-hong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiao-ming Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ying-feng Tu  (屠迎锋)
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ying-feng Tu  (屠迎锋).

Additional information

This work was financially supported by the National Natural Science Foundation of China (No. 21474067) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lu, M., Zhu, X., Li, Xh. et al. Synthesis of cyclic oligo(ethylene adipate)s and their melt polymerization to poly(ethylene adipate). Chin J Polym Sci 35, 1051–1060 (2017). https://doi.org/10.1007/s10118-017-1951-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10118-017-1951-4

Keywords

Search

Navigation