한국군사과학기술학회지 (Journal of the Korea Institute of Military Science and Technology)

  • 제18권2호
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  • Pages.131-138
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  • 2015
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  • 1598-9127(pISSN)
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  • 2636-0640(eISSN)
한국군사과학기술학회 (The Korea Institute of Military Science and Technology)
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분자화약 구조를 포함하는 옥시란계 에너지화 단량체의 설계 및 합성

Design and Synthesis of Novel Energetic Oxirane Monomers Containing a Molecular Explosive Moiety

  • 심엽신 (대구대학교 화학공학과) ;
  • 권영환 (대구대학교 화학공학과) ;
  • 김진석 (국방과학연구소 제1기술연구본부)
  • Shen, Yechen (Department of Chemical Engineering, Daegu University) ;
  • Kwon, Younghwan (Department of Chemical Engineering, Daegu University) ;
  • Kim, Jin Seuk (The 1st Research and Development Institute, Agency for Defense Development)
  • 투고 : 2014.09.19
  • 심사 : 2015.03.20
  • 발행 : 2015.04.05
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초록

Energetic monomers with new design concept were synthesized for energetic prepolymers. Novel energetic monomers consisted of ring-opening polymerizable oxirane and a molecular explosive moiety instead of small explosophores as energetic functional groups. According to the design concept, glycidyl dinitroazetidine (GDNAZ) and glycidyl nitroazetidinol(GNAZO) energetic monomers were synthesized, respectively, and characterized by NMR, EA and GC MS. Heat of formation and detonation performance were calculated by theoretical method to evaluate energy performance of these novel energetic monomers. The result revealed that GDANZ and GNAZO possessed high potential as new energetic monomers for synthesizing energetic prepolymers and binders in PBXs.

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참고문헌

  1. A. Provatas, "Energetic Polymers and Plasticisers for Explosive Formulations - A Review of Recent Advances," DSTO-TR-0966, Aeronautical and Maritime Research Laboratory (AMRL), 2000.
  2. S. W. Ducan and D. C. Mathew, "Evaluation of 1,3,3-Trinitroazetidine (TNAZ) -A High Performance Melt-Castable Explosive," DSTO-TR-0702, Aeronautical and Maritime Research Laboratory (AMRL), 1998.
  3. Y.-H. Kwon, J.-S. Kim, H.-S. Kim, "1-Glycidyl-3,3-dinitroazetidine Containing Explosive Moiety and Preparation Method Thereof", US Patent 7,829,729 B2, 2010.
  4. T. G. Archibald, R. Gilardi, K. Baum, C. George, "Synthesis and X-ray Structure of 1,3,3-Trinitroazetidine," The Journal of Organic Chemistry, Vol. 22, No. 9, pp. 2920-2924, 1990.
  5. A. R. Kartritzky, D. J. Cundy, J. Chen, "Novel Synthesis of 1,3,3-Trinitroazetidine," Journal of Heterocyclic Chemistry, Vol. 31, No. 2, pp. 271-275, 1994. https://doi.org/10.1002/jhet.5570310202
  6. A. P. Marchand, D. Rajgopal, S. G. Bott, T. G. Archibald, "A Novel Approach to the Synthesis of 1,3,3-Trinitroazetidine," The Journal of Organic Chemistry, Vol. 60, No. 15, pp. 4943-4946, 1995. https://doi.org/10.1021/jo00120a049
  7. M. D. Coburn, G. Buntain, B. W. Harris, K. Y. Lee and M. M. Stinecipher, "Synthesis Improvement and Characterization of 1,3,3-Trinitroazetidine (TNAZ)," Joint DOD/DOE Munitions Technology Development Preliminary Report, 1989.
  8. R. L. McKenney Jr., T. G. Floyd, W. E. Stevens, T. G. Archibald, A. P. Marchand, G. V. M. Sharma and S. G. Bott, "Synthesis and Thermal Properties of 1,3-Dinitro-3-(1,3-dinitroazetidine-3-yl)azetidine (TNDAZ) and Its Admixtures with 1,3,3- Trinitroazetidine (TNAZ)", Journal of Energetic Materials, Vol. 16, No. 2-3, pp. 199-235, 1998. https://doi.org/10.1080/07370659808217513
  9. Z. Jalovy, S. Zeman, M. Suceska, P. Vavra, K. Dudek and M. Rajic, "1,3,3-Trinitroazetidine (TNAZ)- Part-I, Synthesis and Properties," Journal of Energetic Materials, Vol. 19, No. 2-3, pp. 219-239, 2001. https://doi.org/10.1080/07370650108216127
  10. A. P. Marchand, D. Rajagopal, S. G. Bott and T. G. Archibald, "Additions of X-Y Across the C(3)-N.sigma.-Bond in 1-Aza-3-ethylbicyclo[1.1.0]butane. Novel Routes to 3-Substituted Azetidines," The Journal of Organic Chemistry, Vol. 59, No. 18, pp. 5499-5501, 1994. https://doi.org/10.1021/jo00097a071
  11. M. D. Coburn, M. D. Kiskey, J. C. Oxley, J. L. Smith, W. Zheng and E. Rgers, "Synthesis and Spectra of Some $^1H-$, $^{13}C$, and $^{15}N$-labled Isomers of 1,3,3-Trinitroazetidine and 3,3-Dinitroazetidinium nitrate," Journal of Energetic Materials, Vol. 16, No. 2-3, pp. 73-99, 1998. https://doi.org/10.1080/07370659808217506
  12. D. L. Heywood, B. Phillips, "The Reaction of Epichlorohydrin with Secondary Amines," Journal of the American Chemical Society, Vol. 80, No. 5, pp. 1257-1259, 1958. https://doi.org/10.1021/ja01538a057
  13. E. Witek, A. Kochanowski and E. Bortel, "On the Reaction of Glycidol with a Secondary Amine," Macromolecular Rapid Communications, Vol. 21, No. 16, pp. 1108-1112, 2000. https://doi.org/10.1002/1521-3927(20001101)21:16<1108::AID-MARC1108>3.0.CO;2-M
  14. P. Politzer, J. S. Murray, J. M. Seminario, P. Lane, M. E. Grice and M. C. Concha, "Computational Characterization of Energetic Materials," Journal of Molecular Structure: Theochem, Vol. 573, No. 1-3, pp. 1-10, 2001. https://doi.org/10.1016/S0166-1280(01)00533-4
  15. D. Habibollahzadeh, M. E. Grice, M. C. Concha, J. S. Murray and P. Politzer, "Nonlocal Density Functional Calculation of Gas Phase Heats of Formation," Journal of Computational Chemistry, Vol. 16, No. 5, pp. 654-658, 1995. https://doi.org/10.1002/jcc.540160513
  16. M. H. Keshavarz and M. K. Tehrani, "A New Method for Determining Gas Phase Heat of Formation of Aromatic Energetic Compounds," Propellants, Explosives, Pyrotechnics, Vol. 32, No. 2, pp. 155-159, 2007. https://doi.org/10.1002/prep.200700016
  17. S. G. Cho, E. M. Goh, J. R. Cho and J. K. Kim, "Theoretical Studies on Molecular and Explosive Properties of 4,4,5,5-Tetranitro-2,2-bi-1H-imidazole (TNBI)," Propellants, Explosives, Pyrotechnics, Vol. 31, No. 1, pp. 33-37, 2006. https://doi.org/10.1002/prep.200600004
  18. J. Zhang, H. M. Xiao and X. D. Gong, "Theoretical studies on Heats of Formation for Polynitrocubanes Using the Density Functional Theory B3LYP Method and Semiempirical MO Methods," Journal of Physical Organic Chemistry, Vol. 14, No. 8, pp. 583-588, 2001. https://doi.org/10.1002/poc.404
  19. D. S. Watt and M. D. Cliff, "TNAZ based Meltcast Explosives: Technology Review and AMRL Research Directions," DSTO-TR-0702, 1998.