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Cardanol with a Covalently Attached Organophosphate Moiety as a Halogen-Free, Intrinsically Flame-Retardant PVC Bio-Plasticizer

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Abstract

Plasticizers that enable flexible polyvinyl chloride (PVC) are usually combustible, restricting the application of PVC in fire-prone scenarios. In this context, intrinsically flame-retardant plasticizers displaying dual function continue to be the focus of intensive research. Despite their efficiency, the majority of these dual-functional plasticizers previously reported contain halogen elements, which, once ignited, emanate toxic and potentially carcinogenic substances, along with toxic gases and smoke, polluting the environment, damaging the biota, and threatening human health. Here, we report a strategy to obtain a halogen-free, intrinsically flame-retardant PVC bio-plasticizer that harnesses the phenolic hydroxyl of naturally occurring cardanol and covalent attachment of an organophosphate moiety. When combined with di-(2-ethylhexyl) phthalate (DOP), the organophosphate-containing cardanol is qualified as a co-plasticizer, while endowing the PVC materials with flame retardancy. Unlike inorganic flame-retardants, the engineered cardanol is compatible with PVC such that the mechanical properties of the PVC materials are not compromised. The rationale underlying the present effort may provide guidance for developing sustainable alternatives to halogen-containing plasticizers to address the sustainability challenge now confronting PVC industry.

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References

  1. S. Y. Pan, D. L. Hou, G. F. Yang, Q. P. Xie, S. X. Yan, Q. Zeng, Z. H. Wang, Y. Chen, and H. J. Fan, J. Leather Sci. Eng., 1, 2 (2019).

    Article  Google Scholar 

  2. M. Q. Wang, J. Yan, S. G. Du, J. S. Zhao, B. Wang, and J. Q. Ding, Fiber. Polym., 15, 1175 (2014).

    Article  CAS  Google Scholar 

  3. S. Y. Pan, D. L. Hou, J. M. Chang, X. Zhou, S. H. Wang, S. X. Yan, Q. Zeng, Z. H. Wang, and Y. Chen, Green Chem., 23, 6430 (2019).

    Article  Google Scholar 

  4. T. Y. Park and S. G. Lee, Fiber. Polym., 8, 620 (2007).

    Article  CAS  Google Scholar 

  5. P. Y. Jia, M. Zhang, C. G. Liu, L. H. Hua, G. D. Feng, C. Y. Bo, and Y. H. Zhou, RSC Adv., 5, 41169 (2015).

    Article  CAS  Google Scholar 

  6. H. D. Lu, L. Song, and Y. Hu, Polym. Adv. Technol., 22, 379 (2011).

    Article  CAS  Google Scholar 

  7. F. C. Wang, J. Chromatogr. A, 886, 225 (2000).

    Article  CAS  Google Scholar 

  8. G. E. Zaikov and S. M. Lomakin, J. Appl. Polym. Sci., 86, 2449 (2002).

    Article  CAS  Google Scholar 

  9. I. D. Veen and J. D. Boer, Chemosphere, 88, 1119 (2012).

    Article  Google Scholar 

  10. P. K. Zhang, Z. Y. Zhang, H. J. Fan, S. Q. Tian, Y. Chen, and J. Yan, RSC Adv., 6, 56610 (2016).

    Article  CAS  Google Scholar 

  11. B. Zhang, Y. J. Jiang, and J. Han, Silicon, 10, 2845 (2018).

    Article  CAS  Google Scholar 

  12. H. C. Erythropel, S. Shipley, A. Börmann, J. A. Nicell, M. Maric, and R. L. Leask, Polymers, 89, 18 (2016).

    Article  CAS  Google Scholar 

  13. Y. Wang, M. M. Hou, Q. N. Zhang, X. W. Wu, H. X. Zhao, Q. Xie, and J. W. Chen, Environ. Sci. Technol., 51, 10991 (2017).

    Article  CAS  Google Scholar 

  14. S. Y. Lu and I. Hamerton, Prog. Polym. Sci., 27, 1661 (2002).

    Article  CAS  Google Scholar 

  15. C. Voirin, S. Caillol, N. V. Sadavarte, B. V. Tawade, B. Boutevin, and P. P. Wadgaonkar, Polym. Chem., 5, 3142 (2014).

    Article  CAS  Google Scholar 

  16. A. Greco, D. Brunetti, G. Renna, G. Mele, and A. Maffezzoli, Polym. Degrad. Stab., 95, 2169 (2010).

    Article  CAS  Google Scholar 

  17. P. Yang, J. Yan, H. Z. Sun, H. J. Fan, Y. Chen, F. Wang, and B. Shi, RSC Adv., 5, 16980 (2015).

    Article  CAS  Google Scholar 

  18. P. K. Zhang, S. Q. Tian, H. J. Fan, Y. Chen, and J. Yan, Prog. Org. Coat., 89, 170 (2015).

    Article  CAS  Google Scholar 

  19. B. I. Chaudhary, B. D. Nguyen, P. Smith, N. Sunday, M. Luong, and A. Zamanskiy, Polym. Eng. Sci., 55, 634 (2015).

    Article  CAS  Google Scholar 

  20. Plastics-Determination of Migration of Plasticizers, ISO 177: 2016 (E).

  21. Standard Test Method for Tensile Properties of Plastics, ASTM D638 (2014).

  22. Standard Test Methods for Vulcanized Rubber and Thermoplastic Elastomers—Tension, ASTM D412 (2016).

  23. Determination of Burning Behaviour by Oxygen Index, Chinese Standard GB/T 2406.1 (2008).

  24. Y. J. Xu, J. Wang, Y. Tan, M. Qi, L. Chen, and Y. Z. Wang, Chem. Eng. J., 337, 30 (2018).

    Article  CAS  Google Scholar 

  25. P. Svoboda, C. Zeng, H. Wang, L. J. Lee, and D. Tomasko, J. Appl. Polym. Sci., 85, 1562 (2002).

    Article  CAS  Google Scholar 

  26. G. Camino, M. P. Luda, and L. Costa, Fire. Polym. II, 6, 77 (1995).

    Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge financial support of this work by National Key Research and Development Program of China (2017YFB0308600), National Natural Science Foundation of China (21878196), Fundamental Research Funds for the Central Universities, China (20826041C4159), and Sichuan University-Sichuan Jinlu contract (19H0266).

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Correspondence to Jun Yan.

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Hou, D., Wang, S., Chang, J. et al. Cardanol with a Covalently Attached Organophosphate Moiety as a Halogen-Free, Intrinsically Flame-Retardant PVC Bio-Plasticizer. Fibers Polym 21, 1649–1656 (2020). https://doi.org/10.1007/s12221-020-9918-4

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