Chinese Journal of Polymer Science

, Volume 37, Issue 7, pp 681–686 | Cite as

Using an Inhibitor to Prevent Plasticizer Migration from Polyurethane Matrix to EPDM Based Substrate

  • Hadi Rezaei-Vahidian
  • Tohid FarajpourEmail author
  • Mahdi Abdollahi


The loss of adhesion between the propellant and insulator is one of the most important problems in solid propellant motors due to migration of plasticizer to interface of propellant and insulator. In this work, the polyurethane (PU) binder containing DOP plasticizer was used as a polymeric matrix and β-cyclodextrin (β-CD) was applied as inhibitor agent to prevent plasticizer migration from the PU matrix into the ethylene propylene diene monomer (EPDM) substrate. To increase the compatibility of β-CD and PU matrix, a derivative of β-CD has been synthesized using toluene diisocyanate (β-CD-TDI). The synthesized derivative was characterized by MALDI-MS and FTIR-ATR analyses. FTIR-ATR results confirmed the formation of bonding between β-CD and the polymeric network while the MALDIMS results showed that the synthesized derivative contained two β-CD and 7 TDI molecules bonded to β-CD. Investigation of the mechanical properties of PU modified by β-CD-TDI showed a decrease in tensile strength and an increase in elongation at break with increasing β-CD-TDI content. DMTA results showed a decrement in crosslinking density by increasing the β-CD-TDI content. Also, to investigate plasticizer migration, extraction of the DOP plasticizer from samples was performed using dichloromethane solvent and its concentration was measured by gas chromatography. The results of migration evaluation after four months showed that using β-CD as an inhibitor agent in the PU binder could prevent the migration of plasticizer to EPDM substrate.


Plasticizer migration β-Cyclodextrin Polyurethane 


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  1. 1.
    Libardi, J.; Ravagnani, S. P.; Morais, A. M. F.; Cardoso, A. R. Study of plasticizer diffusion in a solid rocket motor's bondline. J. Aeros. Technol. Manag. 2009, 1,223–229.CrossRefGoogle Scholar
  2. 2.
    Muthiah, R.; Somasundaran, U.; Verghese, T.; Thornas, V. Energetics and compatibility of plasticizers in composite solid propellants. Def. Sci. J. 1989, 39, 147.CrossRefGoogle Scholar
  3. 3.
    Kumari, D.; Balakshe, R.; Baneijee, S.; Singh, H. Energetic plasticizers for gun & rocket propellants. Rev. J. Chem. 2012, 2, 240–262.CrossRefGoogle Scholar
  4. 4.
    Wypych, G. Handbook of Plasticizers. ChemTec Publishing, 2004.Google Scholar
  5. 5.
    Pröbster, M.; Schmucker, R. Ballistic anomalies in solid rocket motors due to migration effects. Acta Asron. 1986, 13, 599–605.Google Scholar
  6. 6.
    Venkatesan, D.; Srinivasan, M.; Reddy, K. A.; Pendse, V. The migration of plasticizer in solid propellant grains. Polym. Int. 1993, 32, 395–399.CrossRefGoogle Scholar
  7. 7.
    Gottlieb, L.; Bar, S. Migration of plasticizer between bonded propellant interfaces. Propel. Explo. Ppyrotech. 2003, 28, 12–17.CrossRefGoogle Scholar
  8. 8.
    Agrawal, J.; Singh, H. Qualitative assessment of nitroglycerin migration from double–base and composite modified doublebase rocket propellants: Concepts and methods of prevention. Propel. Explos. Pyrotech. 1993, 18, 106–110.CrossRefGoogle Scholar
  9. 9.
    Al Salloum, H.; Saunier, J.; Tfayli, A.; Yagoubi, N. Studying DEHP migration in plasticized PVC used for blood bags by coupling Raman confocal microscopy to UV spectroscopy. Mater. Sci. Eng. C 2016, 61, 56–62.CrossRefGoogle Scholar
  10. 10.
    Chiellini, F.; Ferri, M.; Morelli, A.; Dipaola, L.; Latini, G. Perspectives on alternatives to phthalate plasticized poly(vinyl chloride) in medical devices applications. Prog. Polym. Sci. 2013, 38,1067–1088.CrossRefGoogle Scholar
  11. 11.
    Raeisi, A.; Faghihi, K.; Shabanian, M. Designed biocompatible nano–inhibitor based on poly(ß–cyclodextrin–ester) for reduction of the DEHP migration from plasticized PVC. Carbohydr. Polym. 2017, 174, 858–868.CrossRefGoogle Scholar
  12. 12.
    Yu, B. Y.; Chung, J. W.; Kwak, S. Y. Reduced migration from flexible poly(vinyl chloride) of a plasticizer containing ß–cyclodextrin derivative. Environ. Sci. Technol. 2008, 42, 7522–7527.CrossRefGoogle Scholar
  13. 13.
    Yu, B. Y.; Lee, A. R.; Kwak, S. Y. Gelation/fusion behavior of PVC plastisol with a cyclodextrin derivative and an anti–migration plasticizer in flexible PVC. Eur. Polym. J. 2012, 48, 885–895.CrossRefGoogle Scholar
  14. 14.
    Bernard, L.; Décaudin, B.; Lecoeur, M.; Richard, D.; Bourdeaux, D.; Cueff, R.; Sautou, V.; Group, A. S. Analytical methods for the determination of DEHP plasticizer alternatives present in medical devices: A review. Talanta 2014, 129, 39–54.CrossRefGoogle Scholar
  15. 15.
    Yamasaki, H.; Odamura, A.; Makihata, Y.; Fukunaga, K. Preparation of new photo–crosslinked ß–cyclodextrin polymer beads. Polym. J. 2017, 49, 377.CrossRefGoogle Scholar
  16. 16.
    Xie, A.; Zhang, M.; Inoue, S. I. Influence of diisocyanate on polyurethane elastomers which crosslinked by ß–cyclodextrin. Ope. J. Org. Pol. Mater. 2016, 6, 99–111.CrossRefGoogle Scholar
  17. 17.
    Nandi, S.; Winter, H. H. Swelling behavior of partially cross4li4n4ke7d–4 p4o5l5y.m ers: A ternary system. Macromolecules 2005, 38, 4417–4445.CrossRefGoogle Scholar

Copyright information

© Chinese Chemical Society Institute of Chemistry, Chinese Academy of Sciences Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Hadi Rezaei-Vahidian
    • 1
  • Tohid Farajpour
    • 1
    Email author
  • Mahdi Abdollahi
    • 2
  1. 1.Space Transportation Research InstituteIranian Space Research CenterTehranIran
  2. 2.Polymer Reaction Engineering Department, Faculty of Chemical EngineeringTarbiat Modares UniversityTehranIran

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