Citation: Hadi Rezaei-Vahidian, Tohid Farajpour, Mahdi Abdollahi. Using an Inhibitor to Prevent Plasticizer Migration from Polyurethane Matrix to EPDM Based Substrate[J]. Chinese Journal of Polymer Science, ;2019, 37(7): 681-686. doi: 10.1007/s10118-019-2251-y shu

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

a.
Space Transportation Research Institute, Iranian Space Research Center, Tehran, Iran
b.
Polymer Reaction Engineering Department, Faculty of Chemical Engineering, Tarbiat Modares University, Tehran, Iran

Author Bio: Email: hrvahidian_1984@yahoo.com (Hadi Rezaei-Vahidian)
tohid20104@yahoo.com (Tohid Farajpour)
abdollahim@modares.ac.ir (Mahdi abdollahi)
Corresponding author: Tohid Farajpour, tohid20104@yahoo.com
Received Date: 23 November 2018
Revised Date: 1 January 2019
Accepted Date: 1 January 2019
Available Online: 23 April 2019

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 MALDI-MS 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
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. doi: 10.5028/jatm.2009.0102223229
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. doi: 10.14429/dsj.39.4759
3. [3]
  Kumari, D.; Balakshe, R.; Banerjee, S.; Singh, H. Energetic plasticizers for gun & rocket propellants. Rev. J. Chem. 2012, 2, 240-262. doi: 10.1134/S207997801203003X
4. [4]
  Wypych, G. Handbook of Plasticizers. ChemTec Publishing, 2004.
5. [5]
  Pröbster, M.; Schmucker, R. Ballistic anomalies in solid rocket motors due to migration effects. Acta Astron. 1986, 13, 599-605. doi: 10.1016/0094-5765(86)90050-0
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. doi: 10.1002/(ISSN)1097-0126
7. [7]
  Gottlieb, L.; Bar, S. Migration of plasticizer between bonded propellant interfaces. Propel. Explo. Pyrotech. 2003, 28, 12-17. doi: 10.1002/prep.200390000
8. [8]
  Agrawal, J.; Singh, H. Qualitative assessment of nitroglycerin migration from double-base and composite modified double-base rocket propellants: Concepts and methods of prevention. Propel. Explos. Pyrotech. 1993, 18, 106-110. doi: 10.1002/(ISSN)1521-4087
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. doi: 10.1016/j.msec.2015.12.008
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. doi: 10.1016/j.progpolymsci.2013.03.001
11. [11]
  Raeisi, A.; Faghihi, K.; Shabanian, M. Designed biocompatible nano-inhibitor based on poly(β-cyclodextrin-ester) for reduction of the DEHP migration from plasticized PVC. Carbohydr. Polym. 2017, 174, 858-868. doi: 10.1016/j.carbpol.2017.06.105
12. [12]
  Yu, B. Y.; Chung, J. W.; Kwak, S. Y. Reduced migration from flexible poly(vinyl chloride) of a plasticizer containing β-cyclodextrin derivative. Environ. Sci. Technol. 2008, 42, 7522-7527. doi: 10.1021/es800895x
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. doi: 10.1016/j.eurpolymj.2012.02.008
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. doi: 10.1016/j.talanta.2014.04.069
15. [15]
  Yamasaki, H.; Odamura, A.; Makihata, Y.; Fukunaga, K. Preparation of new photo-crosslinked β-cyclodextrin polymer beads. Polym. J. 2017, 49, 377. doi: 10.1038/pj.2016.127
16. [16]
  Xie, A.; Zhang, M.; Inoue, S. I. Influence of diisocyanate on polyurethane elastomers which crosslinked by β-cyclodextrin. Ope. J. Org. Pol. Mater. 2016, 6, 99-111. doi: 10.4236/ojopm.2016.63010
17. [17]
  Nandi, S.; Winter, H. H. Swelling behavior of partially cross-linked polymers: a ternary system. Macromolecules 2005, 38, 4447-4455. doi: 10.1021/ma048335e
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