DOI QR코드

DOI QR Code

Synthesis and Characterization of 1-DABTR as Insensitive Energetic Plasticizer

둔감 에너지 가소제 1-DABTR의 합성 및 특성 평가

  • Lee, Woonghee (Energetic Materials & Pyrotechnics Department, Hanwha Corporation Defence R&D Center) ;
  • Kim, Minjun (Energetic Materials & Pyrotechnics Department, Hanwha Corporation Defence R&D Center) ;
  • Park, Youngchul (The 4th R&D Institute - 1st Directorate, Agency for Defense Development) ;
  • Lee, Bumjae (Department of Fine Chemical Engineering and Applied Chemistry, Chungnam National University)
  • Received : 2017.02.01
  • Accepted : 2017.07.16
  • Published : 2017.12.01

Abstract

Plasticizers play roles in increasing plasticity or fluidity during mixing. Representative plasticizers are DOS, DOA, IDP and BTTN. In particular, BTTN is an energy plasticizer that helps propellant performance and is widely used. However these compounds are sensitive relatively. So, in order to develop insensitive energetic plasticizer, synthesis of one of the derivatives of triazole, 4,5-bis (azido methyl)-(1-butyl)-1,2,3-triazole (1-DABTR), was studied. Also, the compound was characterized by NMR, IR spectroscopy, and physicochemical properties such as glass transition temperature, melting point, decomposition temperature, density, viscosity and impact sensitivity were measured. In addition, the heats of formation (${\Delta}H_f$) of 1-DABTR was also calculated using Gaussian 09.

가소제는 추진제 혼화 시 흐름성과 공정성을 향상시키는 역할을 한다. 대표적인 가소제로서 DOS, DOA, IDP, BTTN 등이 있다. 특히 BTTN은 에너지 가소제로서 추진제 성능에 도움을 주는 물질이며, 다양하게 사용되고 있다. 그러나 이 물질들은 충격감도가 비교적 민감하다는 단점이 있다. 본 연구에서는 둔감한 에너지 가소제를 개발하기 위해 트리아졸 계열의 4,5-bis (azidomethyl)-(1-butyl)-1,2,3-triazole (1-DABTR)을 합성하고 이화학적 특성 분석을 하였다. 또한, 분광분석(NMR, IR)을 통해 1-DABTR의 구조를 분석하였고, 유리전이온도, 녹는점, 분해온도, 밀도, 점도, 충격감도 등의 물리적 특성을 측정하였다. 그리고 Gaussian 09를 이용하여 생성열을 계산하였다.

Keywords

References

  1. Kubota, N., Propellants and Explosives, Thermochemical Aspects of Combustion, 2nd ed., Wiley-VCH, New York, N.Y., U.S.A., 2007.
  2. Agrawal, J.P., High Energy Materials, 1th ed., Wiley-VCH, New York, N.Y., U.S.A., 2010.
  3. Boschan, R., Merrow, R.T. and Dolah, R.W., "The Chemistry of Nitrate Esters," Chemical Reviews, Vol. 55, No. 3, pp. 485-510, 1955. https://doi.org/10.1021/cr50003a001
  4. Agrawal, J.P., Surve, R.N. and Sonawane, S.H., "Some Aromatic Nitrate Esters: Synthesis, Structural Aspects, Thermal and Explosive Properties," Journal of Hazardous Materials, Vol. 77, No. 1, pp. 11-31, 2000. https://doi.org/10.1016/S0304-3894(00)00235-1
  5. Wingborg, N. and Eldster, C., "2,2-Dinitro -1,3-Bis-Nitrooxy-Propane(NPN): A New Energetic Plasticizer," Propellants, Explosives, Pyrotechnics, Vol. 27, No. 6, pp. 314-319, 2002. https://doi.org/10.1002/prep.200290000
  6. Ye, C., Gao, H., Boatz, J.A., Drake, G.W., Twamley, B. and Shreeve, J.M., "Polyazido Pyrimidines: High-Energy Compounds and Precursors to Carbon Nanotubes," Angewandte Chemie International Edition, Vol. 45, No 43, pp. 7262-7265, 2006. https://doi.org/10.1002/anie.200602778
  7. Kumari, D., Yamajala, K.D.B., Asthana, S.N., Raju, K. and Banerjee, S., "Application of Azido Esters as Energetic Plasticizers for LOVA Propellant Formulations," Propellants, Explosives, Pyrotechnics, Vol. 38, No. 6, pp. 805-809, 2013. https://doi.org/10.1002/prep.201300070
  8. Huisgen, R., "1,3-Dipolare Cycloadditionen Ruckschau und Ausblick," Angewandte Chemie, Vol. 75, No. 13, pp. 604-637, 1963. https://doi.org/10.1002/ange.19630751304
  9. Kolb, H.C., Finn, M.G. and Sharpless, K.B., "Click Chemistry: Diverse Chemical Function form a Few Good Reactions," Angewandte Chemie International Edition, Vol. 40, No. 11, pp. 2004-2021, 2001. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
  10. Vsevolod, V.R., Luke, G.G., Valery, V.F. and Sharpless, K.B., "A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective Ligation of Azides and Terminal Alkynes," Angewandte Chemie International Edition, Vol. 41, No. 14, pp. 2596-2599, 2002. https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
  11. Jon, C.L. and Sharpless, K.B., "The Banert Cascade: A Synthetic Sequence to Polyfunctional NH-1,2,3-Triazoles," Synthesis, No. 9, pp. 1514-1520, 2005.
  12. Parr, R.G. and Yang, W., Density Functional Theory of Atoms and Molecules, 1th ed., Oxford University Press, New York, N.Y., U.S.A., 1989.