Skip to main content
SpringerLink
Log in

Effect of Dimethyl 1,4-Cyclohexane Dicarboxylate on Mechanical Properties and Crystallization Behavior of Polytrimethylene Terephthalate Co-Polymer

  • Article
  • Published:
Macromolecular Research Aims and scope Submit manuscript

Abstract

Dimethyl 1,4-cyclohexane dicarboxylate (DMCD) is formed as an impurity when dimethyl terephthalate (DMT) is manufactured from biomass. Because the boiling point of DMCD is similar to that of DMT, DMCD is known to add considerable cost to the separation and refinement. This prompted us to investigate the effect of the presence of varying amounts of DMCD on the physical properties of poly(trimethylene terephthalate) (PTT), which is manufactured from DMT. In the present study, a small amount of DMCD (1-5 mol% of DMT) was added when manufacturing PTT through the polycondensation of DMT and propanediol (PDO). The results of the analysis of the thermal properties indicated that the glass transition temperature and melting temperature showed a decreasing tendency as the DMCD content increased. The thermal stability increased by 25 °C compared to that of virgin PTT. The iso-thermal scanning analysis showed that the crystallization rate with 1 mol% of DMCD increased compared to that of virgin PTT, whereas the crystallization rate decreased with a higher DMCD content. The mechanical properties are noteworthy. The tensile strength and the tensile strain were simultaneously improved with the addition of DMCD, and the initial modulus remained nearly constant within the range of this experiment. Particularly, the tensile strength increased by a maximum of 15% (76.5 MPa) compared to that of virgin PTT. The physical properties of the PTT co-polyester significantly changed when the DMCD content was 2 mol%. Overall, the thermal properties remained similar, the crystallization rate increased, and the thermal stability and mechanical properties were significantly improved up to 2 mol%. Furthermore, the viscosity and crystal structure were examined by capillary rheometry and X-ray diffraction (XRD) to investigate the changes in these two properties. We concluded that the presence of bio-byproducts such as DMCD enhances the mechanical properties of PTT, such as the tensile strength and strain.

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. S. Spierling, E. Knüpffer, H. Behnsen, M. Mudersbach, H. Krieg, S. Springer, S. Albrecht, C. Herrmann, and H. J. Endres, J. Cleaner Prod., 185, 476 (2018).

  2. H. Kawaguchi, C. Ogino, and A. Kondo, Bioresour. Technol., 245, 1413 (2017).

    Article  CAS  Google Scholar 

  3. H. H. Chuah, Polym. Eng. Sci., 41, 308 (2001).

    Article  CAS  Google Scholar 

  4. S. Kim, H. Kim, and B. Nam, Asian J. Chem., 25, 5143 (2013).

    Article  Google Scholar 

  5. W. J. Bae, W. H. Jo, and Y. H. Park, Macromol. Res., 10, 145 (2002).

    Article  CAS  Google Scholar 

  6. W. Liu, A. K. Mohanty, L. T. Drzal, M. Misra, J. V. Kurian, R. W. Miller, and N. Strickland, Ind. Eng. Chem. Res., 44, 857 (2005).

    Article  CAS  Google Scholar 

  7. J. Wang, C. Wang, and M. Run, Int. J. Polym. Sci., 2013 (2013).

    Google Scholar 

  8. S. K. Na, B. G. Kong, C. Choi, M. K. Jang, J. W. Nah, J.-G. Kim, and B. W. Jo, Macromol. Res., 13, 88 (2005).

    Article  CAS  Google Scholar 

  9. Z. Liu, K. Chen, and D. Yan, Eur. Polym. J., 39, 2359 (2003).

    Article  CAS  Google Scholar 

  10. N. Dangseeyun, P. Srimoaon, P. Supaphol, and M. Nithitanakul, Thermochim. Acta, 409, 63 (2004).

    Article  CAS  Google Scholar 

  11. K. J. Hsiao, S. P. Lee, D. C. Kong, and F. L. Chen, J. Appl. Polym. Sci., 102, 1008 (2006).

    Article  CAS  Google Scholar 

  12. H. Zou, C. Yi, L. Wang, and W. Xu, Polym. Bull., 64, 471 (2010).

    Article  CAS  Google Scholar 

  13. J. M. Huang and F. C. Chang, J. Polym. Sci., Part B: Polym. Phys., 38, 934 (2000).

    Article  CAS  Google Scholar 

  14. W. J. Yoon, K. S. Oh, J. M. Koo, J. R. Kim, K. J. Lee, and S. S. Im, Macromolecules, 46, 2930 (2013).

    Article  CAS  Google Scholar 

  15. P. D. Hong, W. T. Chung, and C. F. Hsu, Polymer, 43, 3335 (2002).

    Article  CAS  Google Scholar 

  16. C. Berti, A. Celli, P. Marchese, E. Marianucci, G. Barbiroli, and F. Di Credico, Macromol. Chem. Phys., 209, 1333 (2008).

    Article  CAS  Google Scholar 

  17. Y. Liu and S. R. Turner, J. Polym. Sci., Part A: Polym. Chem., 48, 2162 (2010).

    Article  CAS  Google Scholar 

  18. M. Albanese, J. Boyenval, P. Marchese, S. Sullalti, and A. Celli, AIMS Mol. Sci., 3, 32 (2016).

    Article  CAS  Google Scholar 

  19. A. Celli, P. Marchese, S. Sullalti, C. Berti, and G. Barbiroli, Macromol. Chem. Phys., 212, 1524 (2011).

    Article  CAS  Google Scholar 

  20. C. Berti, E. Binassi, A. Celli, M. Colonna, M. Fiorini, P. Marchese, E. Marianucci, M. Gazzano, F. Di Credico, and D. J. Brunelle, J. Polym. Sci., Part B: Polym. Phys., 46, 619 (2008).

    Article  CAS  Google Scholar 

  21. B. Vanhaecht, M. N. Teerenstra, D. R. Suwier, R. Willem, M. Biesemans, and C. E. Koning, J. Polym. Sci., Part A: Polym. Chem., 39, 833 (2001).

    Article  CAS  Google Scholar 

  22. C. Berti, A. Celli, P. Marchese, E. Marianucci, S. Sullalti, and G. Barbiroli, Macromol. Chem. Phys., 211, 1559 (2010).

    Article  CAS  Google Scholar 

  23. T. Sandhya, C. Ramesh, and S. Sivaram, Macromolecules, 40, 6906 (2007).

    Article  CAS  Google Scholar 

  24. L. Wang, Z. Xie, X. Bi, X. Wang, A. Zhang, Z. Chen, J. Zhou, and Z. Feng, Polym. Degrad. Stab., 91, 2220 (2006).

    Article  CAS  Google Scholar 

  25. S. W. Hu, H. S. Myung, J. S. Bae, E. S. Yoo, and S. S. Im, Fibers Polym., 1, 76 (2000).

    Article  CAS  Google Scholar 

  26. Y. M. Sun and C. S. Wang, Eur. Polym. J., 35, 1087 (1999).

    Article  CAS  Google Scholar 

  27. H. Ki and O. O. Park, Polymer, 42, 1849 (2001).

    Article  CAS  Google Scholar 

  28. S. Paszkiewicz, A. Szymczyk, K. Livanov, H. Wagner, and Z. Roslaniec, eXPRESS Polym. Lett., 9, 509 (2015).

    Article  CAS  Google Scholar 

  29. C. F. Ou, J. Polym. Sci., B: Polym. Phys., 41, 2902 (2003).

    Article  CAS  Google Scholar 

  30. G. Wei, D. Hua, and L. Gu, J. Appl. Polym. Sci., 101, 3330 (2006).

    Article  CAS  Google Scholar 

  31. S. H. Kim, S. H. Ahn, and T. Hirai, Polymer, 44, 5625 (2003).

    Article  CAS  Google Scholar 

  32. T. Gopakumar, J. Lee, M. Kontopoulou, and J. Parent, Polymer, 43, 5483 (2002).

    Article  CAS  Google Scholar 

  33. S. Paszkiewicz, A. Szymczyk, Z. Špitalský, J. Mosnácek, K. Kwiatkowski, and Z. Roslaniec, Eur. Polym. J., 50, 69 (2014).

    Article  CAS  Google Scholar 

  34. A. Szymczyk, S. Paszkiewicz, and Z. Roslaniec, Polym. Bull., 70, 1575 (2013).

    Article  CAS  Google Scholar 

  35. R. Sharma, P. Jain, and S. D. Sadhu, Arabian J. Sci. Eng., 1 (2018).

    Google Scholar 

  36. A. Pei, Q. Zhou, and L. A. Berglund, Compos. Sci. Technol., 70, 815 (2010).

    Article  CAS  Google Scholar 

  37. P. Srimoaon, N. Dangseeyun, and P. Supaphol, Eur. Polym. J., 40, 599 (2004).

    Article  CAS  Google Scholar 

  38. P. Krutphun and P. Supaphol, Eur. Polym. J., 41, 1561 (2005).

    Article  CAS  Google Scholar 

  39. I. Aravind, A. Boumod, Y. Grohens, and S. Thomas, Ind. Eng. Chem. Res., 49, 3873 (2010).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Korea Institute of Industrial Technology, 6 Cheomdangwagiro 208gil, Buk-gu, Gwangju, 61012, Korea

    Han Na Kim, Je Sung Youm & Jeong Cheol Kim

  2. Sebang Industrial, 236 Sonjae-ro, Gwangsan-gu, Gwangju, 62230, Korea

    Daesun Park

  3. Huvis, 343, Hakdong-ro, Gangnam-gu, Seoul, 06060, Korea

    Bookyeong Jang

Authors
  1. Han Na Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Daesun Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Je Sung Youm
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bookyeong Jang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jeong Cheol Kim
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jeong Cheol Kim.

Additional information

Acknowledgment: This work was supported by the Ministry of Strategy and Finance (MOSF, Korea) [No.JA180036].

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kim, H.N., Park, D., Youm, J.S. et al. Effect of Dimethyl 1,4-Cyclohexane Dicarboxylate on Mechanical Properties and Crystallization Behavior of Polytrimethylene Terephthalate Co-Polymer. Macromol. Res. 27, 182–190 (2019). https://doi.org/10.1007/s13233-019-7049-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13233-019-7049-9

Keywords

Search

Navigation