Journal of Industrial and Engineering Chemistry

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
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Synthesis and characterization of bis(2,2-dinitropropyl ethylene) formal plasticizer for energetic binders

  • Published : 2012.05.25
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Abstract

A novel gem-dinitro bis(2,2-dinitropropyl ethylene) formal (BDNPEF) was synthesized and its potential application to plasticize energetic binders was investigated. BDNPEF was synthesized from aldol condensation of formaldehyde with 2,2-dinitropropanol (DNP-OH) and ethylene glycol (EG), followed by purification. One of the byproducts of this process was bis(2,2-dinitropropyl) formal (BDNPF), which is currently used as an energetic plasticizer. Compared to commercial nitro plasticizers, BDNPEF synthesized in this study showed good plasticization efficiency with a decrease in glass transition temperature ($T_{g}$) and viscosity of uncured glycidyl azide polymer (GAP) blends, as well as substantial ability to plasticize the GAP-based polyurethanes (PUs). BDNPEF has potential applications as an energetic plasticizer to engineer the properties of the GAP-based energetic PU binders.

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References

  1. G. Wypych, Handbook of Plasticizers, ChemTec Publishing, Toronto, Canada, 2004
  2. M. Rahman, C.S. Brazel, Prog. Polym. Sci. 29 (2004) 1223. https://doi.org/10.1016/j.progpolymsci.2004.10.001
  3. C. Caner, P.J. Vergano, J.L. Wiles, J. Food Sci. 6 (1998) 1049.
  4. F. Debeaufort, A. Voilley, J. Agric. Food Chem. 45 (1997) 685. https://doi.org/10.1021/jf9606621
  5. J.P. Agrawal, R.D. Hodgson, Organic Chemistry of Explosives, John Wiley & Sons Ltd., West Sussex, England, 2007.
  6. J.R. Goleniewski, J.A. Roberts, U.S. Patent 5,783,769 (1998).
  7. Y.P. Ji, P.R. Li, W. Wang, Y. Lan, F. Ding, Chin. J. Explos. Propellants 28 (2005) 47.
  8. R.H. Taylor, H. Ala, U.S. Patent 5,334,270 (1996).
  9. R.H. Taylor, H. Ala, U.S. Patent 5,579,634 (1996).
  10. K. Menke, S. Eisele, Propellants Explos. Pyrotech. 22 (1997) 112. https://doi.org/10.1002/prep.19970220304
  11. N. Marsh, A. Marsh, Clin. Exp. Pharmacol. Physiol. 27 (2000) 313. https://doi.org/10.1046/j.1440-1681.2000.03240.x
  12. J. Akhavan, The Chemistry of Explosives, 2nd ed., The Royal Society of Chemistry, UK, 2004.
  13. A.T. Camp, L.A. Dickinson, P.R. Mosher, U.S. Patent 3,634,158 (1972).
  14. S.B. Preston, U.S. Patent 5,454,891 (1995).
  15. M.A. Barrio, J. Hu, P.Z. Zhou, N. Cauchon, J. Pharm. Biomed. Anal. 41 (2006) 738. https://doi.org/10.1016/j.jpba.2005.12.033
  16. M. Jang, R.M. Kamens, Environ. Sci. Technol. 35 (2001) 4758. https://doi.org/10.1021/es010790s
  17. J.S. Kim, J.R. Cho, K.D. Lee, J.K. Kim, U.S. Patent 0,056,663 (2007).
  18. M.A. Lenskii, E.E. Shul'ts, A.A. Androshchuk, G.A. Tolstikov, Russ. J. Org. Chem. 45 (2009) 1772. https://doi.org/10.1134/S1070428009120045
  19. K.C. Barsanti, J.F. Pankow, Atmos. Environ. 38 (2004) 4371. https://doi.org/10.1016/j.atmosenv.2004.03.035
  20. M. Jang, N.M. Czoschke, S. Lee, R.M. Kamens, Science 298 (2002) 814. https://doi.org/10.1126/science.1075798
  21. M.J. Zohuriaan, F. Shokrolahi, Polym. Test. 23 (2004) 575. https://doi.org/10.1016/j.polymertesting.2003.11.001
  22. M.M. Feldstein, A. Roos, C. Chevallier, C. Creton, E.E. Dormidontova, Polymer 44 (2003) 1819. https://doi.org/10.1016/S0032-3861(03)00046-6
  23. L.M. Her, S.L. Nail, Pharm. Res. 11 (1994) 54. https://doi.org/10.1023/A:1018989509893
  24. M.-S. Chi, J. Polym. Sci. A: Polym. Chem. 19 (1981) 1767. https://doi.org/10.1002/pol.1981.170190716
  25. N. Wingborg, C. Eldsater, Propellants Explos. Pyrotech. 27 (2002) 314. https://doi.org/10.1002/prep.200290000
  26. B.S. Min, Propellants Explos. Pyrotech. 33 (2008) 131. https://doi.org/10.1002/prep.200700241

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