Synthesis and characterization of bis(2,2-dinitropropyl ethylene) formal plasticizer for energetic binders

Yun Chen; Younghwan Kwon; Jin Seuk Kim

Journal of Industrial and Engineering Chemistry, Vol.18, No.3, 1069-1075, May, 2012

DOI10.1016/j.jiec.2011.12.006 Export Citation

Synthesis and characterization of bis(2,2-dinitropropyl ethylene) formal plasticizer for energetic binders

Yun Chen, Younghwan Kwon^†, and Jin Seuk Kim¹

Department of Chemical Engineering, Daegu University, Gyeongsan, Gyeongbuk 712-714, Republic of Korea
¹The 4th R&D Institute – 2nd Directorate, ADD, Yuseong PO Box 35-42, Daejeon 305-600, Republic of Korea

E-mail:

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 (Tg) 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.

Keywords:Energetic plasticizer;Plasticization;Energetic binder;Gem-dinitro formal

[References]

Wypych G, Handbook of Plasticizers, ChemTec Publishing, Toronto, Canada (2004)
Rahman M, Brazel CS, Prog. Polym. Sci., 29, 1223 (2004)
Caner C, Vergano PJ, Wiles JL, J. Food Sci., 6, 1049 (1998)
Debeaufort F, Voilley A, J. Agric. Food Chem., 45, 685 (1997)
Agrawal JD, Hodgson RD, Organic Chemistry of Explosives, John Wiley & Sons Ltd., West Sussex, England (2007)
Goleniewski JR, Roberts JA, U.S. Patent 5,783,769 (1998)
Ji YP, Li PR, Wang W, Lan Y, Ding F, Chin. J. Explos. Propellants., 28, 47 (2005)
Taylor RH, Ala H, U.S. Patent 5,334,270 (1996)
Taylor RH, H. Ala, U.S. Patent 5,579,634 (1996)
Menke K, Eisele S, Propellants Explos. Pyrotech., 22, 112 (1997)
Marsh N, Marsh A, Clin. Exp. Pharmacol. Physiol., 27, 313 (2000)
Akhavan J, The Chemistry of Explosives, 2nd ed., The Royal Society of Chemistry,UK (2004)
Camp AT, Dickinson LA, Mosher PR, U.S. Patent 3,634,158 (1972)
Preston SB, U.S. Patent 5,454,891 (1995)
Barrio MA, Hu J, Zhou PZ, Cauchon N, J. Pharm. Biomed. Anal., 41, 738 (2006)
Jang M, Kamens RM, Environ. Sci. Technol., 35, 4758 (2001)
Kim JS, Cho JR, Lee KD, Kim JK, U.S. Patent 0,056,663 (2007)
Lenskii MA, Shul’ts EE, Androshchuk AA, Tolstikov GA, Russ. J. Org. Chem., 45, 1772 (2009)
Barsanti KC, Pankow JF, Atmos. Environ., 38, 4371 (2004)
Jang M, Czoschke NM, Lee S, Kamens RM, Science., 298, 814 (2002)
Zohuriaan MJ, Shokrolahi F, Polym. Test., 23, 575 (2004)
Feldstein MM, Roos A, Chevallier C, Creton C, Dormidontova EE, Polymer, 44(6), 1819 (2003)
Her LM, Nail SL, Pharm. Res., 11, 54 (1994)
Chi MS, J. Polym. Sci. A: Polym. Chem., 19, 1767 (1981)
Wingborg N, Eldsater C, Propellants Explos. Pyrotech., 27, 314 (2002)
Min BS, Propellants Explos. Pyrotech., 33, 131 (2008)

[1] Wypych G, Handbook of Plasticizers, ChemTec Publishing, Toronto, Canada (2004)

[2] Rahman M, Brazel CS, Prog. Polym. Sci., 29, 1223 (2004)

[3] Caner C, Vergano PJ, Wiles JL, J. Food Sci., 6, 1049 (1998)

[4] Debeaufort F, Voilley A, J. Agric. Food Chem., 45, 685 (1997)

[5] Agrawal JD, Hodgson RD, Organic Chemistry of Explosives, John Wiley & Sons Ltd., West Sussex, England (2007)

[6] Goleniewski JR, Roberts JA, U.S. Patent 5,783,769 (1998)

[7] Ji YP, Li PR, Wang W, Lan Y, Ding F, Chin. J. Explos. Propellants., 28, 47 (2005)

[8] Taylor RH, Ala H, U.S. Patent 5,334,270 (1996)

[9] Taylor RH, H. Ala, U.S. Patent 5,579,634 (1996)

[10] Menke K, Eisele S, Propellants Explos. Pyrotech., 22, 112 (1997)

[11] Marsh N, Marsh A, Clin. Exp. Pharmacol. Physiol., 27, 313 (2000)

[12] Akhavan J, The Chemistry of Explosives, 2nd ed., The Royal Society of Chemistry,UK (2004)

[13] Camp AT, Dickinson LA, Mosher PR, U.S. Patent 3,634,158 (1972)

[14] Preston SB, U.S. Patent 5,454,891 (1995)

[15] Barrio MA, Hu J, Zhou PZ, Cauchon N, J. Pharm. Biomed. Anal., 41, 738 (2006)

[16] Jang M, Kamens RM, Environ. Sci. Technol., 35, 4758 (2001)

[17] Kim JS, Cho JR, Lee KD, Kim JK, U.S. Patent 0,056,663 (2007)

[18] Lenskii MA, Shul’ts EE, Androshchuk AA, Tolstikov GA, Russ. J. Org. Chem., 45, 1772 (2009)

[19] Barsanti KC, Pankow JF, Atmos. Environ., 38, 4371 (2004)

[20] Jang M, Czoschke NM, Lee S, Kamens RM, Science., 298, 814 (2002)

[21] Zohuriaan MJ, Shokrolahi F, Polym. Test., 23, 575 (2004)

[22] Feldstein MM, Roos A, Chevallier C, Creton C, Dormidontova EE, Polymer, 44(6), 1819 (2003)

[23] Her LM, Nail SL, Pharm. Res., 11, 54 (1994)

[24] Chi MS, J. Polym. Sci. A: Polym. Chem., 19, 1767 (1981)

[25] Wingborg N, Eldsater C, Propellants Explos. Pyrotech., 27, 314 (2002)

[26] Min BS, Propellants Explos. Pyrotech., 33, 131 (2008)