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Synthesis and Characterization of New Energetic Plasticizers: Benzoyl-terminated Poly(epichlorohydrin) Modified by Phenylhydrazine and its Derivatives

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Języki publikacji
EN
Abstrakty
EN
Nitrobenzoyl-terminated poly(epichlorohydrin) (NB-PECH) was synthesized through the reaction of poly(epichlorohydrin) (PECH) with 3-nitrobenzoyl chloride. The NB-PECH was then modified by reaction with phenylhydrazine, 4-nitrophenylhydrazine and 2,4-dinitrophenylhydrazine, and these derivatives were evaluated as plasticizers. Poly(epichlorohydrin), poly(epichlorohydrin) with terminal 3-nitrobenzoyl groups (NB-PECH), terminal nitrobenzoyl poly(epichlorohydrin-phenylhydrazine) (NB-PECH-PH), terminal nitrobenzoyl poly(epichlorohydrin-4-nitrophenylhydrazine) (NB-PECH-4-NPH) and terminal nitrobenzoyl poly(epichlorohydrin-2,4-dinitrophenylhydrazine) (NB-PECH-2,4-DNPH) were examined by Ultraviolet-Visible spectroscopy (UV-VIS), Fourier Transform Infrared spectroscopy (FT-IR), Proton Nuclear Magnetic Resonance (1H NMR) spectrometry, elemental analysis of carbon, hydrogen and nitrogen (CHN) an Thermal Analysis methods: Thermogravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC). In the TGA examination, the highest thermal stability was exhibited by NB-PECH. The glass transition temperature for the potential plasticizers was determined from their DSC curves. The DSC tests indicated that the highest energy of the plasticizers was exhibited by NB-PECH-2,4-DNPH containing two nitro groups. In addition, by comparing the thermograms of the samples heated with poly(tetrahydrofuran) the energy content of the NB-PECH-PH, NB-PECH-4-NPH and NB-PECH-2,4-DNPH plasticizers was clearly demonstrated.
Rocznik
Strony
323--343
Opis fizyczny
Bibliogr. 29 poz., rys., tab.
Twórcy
  • Department of Chemistry, College of Science, Malek-ashtar University of Technology, P.O. Box 83145-115, Shahin-shahr, Iran
  • Department of Chemistry, College of Science, Malek-ashtar University of Technology, P.O. Box 83145-115, Shahin-shahr, Iran
  • Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
  • Department of Chemistry, College of Science, Malek-ashtar University of Technology, P.O. Box 83145-115, Shahin-shahr, Iran
  • Department of Chemistry, College of Science, Malek-ashtar University of Technology, P.O. Box 83145-115, Shahin-shahr, Iran
Bibliografia
  • [1] Ghosh, K.; Athar, J.; Pawar, S.; Polke, B.G. Synthesis, Characterization, and Rheological Evaluation of 1,3-Diazido-2-ethyl-2-nitropropane as an Energetic Plasticizer. J. Energ. Mater. 2012, 30(2): 107-123.
  • [2] Pei, J.-F.; Zhao, F-Q.; Lin Lu, H.; Duo song, X. Compatibility Study of BAMO GAP Copolymer with Some Energetic Materials. J. Therm. Anal. Calorim. 2016, 124(3): 1301-1307.
  • [3] Zhao, Y.; Zhang, X.; Zhang, W.; Xu, H.; Xie, W.; Du, J. Simulation and Experimental on the Solvation Interaction between the GAP Matrix and Insensitive Energetic Plasticizers in Solid Propellants. J. Phys. Chem. A. 2016, 120(5): 765-770.
  • [4] Liu, X.; Sun, X.; Hong, X.; Pang, A.; Qiao, Y. Research Progress of Bonding Agents for Nitramine Composite Solid Propellants. Int J. Astrophys Space Sci. 2018, 6(2): 44.
  • [5] Kumari, D.; Sing, H.; Patil, M.; Thiel, W. Synthesis, Characterization, Thermal and Computational Studies of Novel Tetra-azido Esters as Energetic Plasticizers. Thermochim. Acta 2013, 562: 96-104.
  • [6] Shee, S.K.; Shah, P.N.; Athar, J.; Dey, A.; Soman, R.R.; Sikder, A.K. Understanding the Compatibility of the Energetic Binder PolyNIMMO with Energetic Plasticizers: Experimental and DFT Studies. Propellants, Explos., Pyrotech. 2017, 42(2):167-174.
  • [7] Abusaidi, H.; Ghorbani, M.; Ghaieni, H.R. Development of Composite Solid Propellant Based on Nitro Functionalized Hydroxyl‐Terminated Polybutadiene. Propellants, Explos., Pyrotech. 2017, 42(6): 671-675.
  • [8] Wingard, L.A.; Guzman, P.E.; Johnson, E.C.; Sabatini, J.; Drake, G.W. Synthesis of bis‐Isoxazole‐bis‐methylene Dinitrate: A Potential Nitrate Plasticizer and Meltcastable Energetic Material. Chem. Plus. Chem. 2017, 82(2): 195-198.
  • [9] Qi, X.; Li, H.; Zhao, Y.; Yan, N. Comparison of the Structural and Physical Properties of Nitrocellulose Plasticized by N-Butyl-N-(2-nitroxy-ethyl) Nitramine and Nitroglycerin: Computational Simulation and Experimental Studies. J. Hazard. Mater. 2019, 362: 303-310.
  • [10] Chen, Y.; Kwon, Y.; Kim, J.S. Synthesis and Characterization of bis(2,2- Dinitropropyl Ethylene) Formal Plasticizer for Energetic Binders. J. Ind. Eng. Chem. 2012, 18(3): 1069-1075.
  • [11] Abrishami, F.; Zarei, A.; Karegar, M. Synthesis of Novel Plasticizers Based on Poly(ε-caprolactone) and a Consideration of Their Influence on Nitroglycerine Migration in Double Base Solid Propellants. Cent. Eur. J. Energ. Mater. 2018, 15(1): 150-161.
  • [12] Kumari, D.; Balakshe, R.; Banerjee, S.; Singh, H. Energetic Plasticizers for Gun and Rocket Propellants. Rev. J. Chem. 2012, 2(3): 240-262.
  • [13] Lemos, M.F.; Bohn, M.A. DMA of Polyester-based Polyurethane Elastomers for Composite Rocket Propellants Containing Different Energetic Plasticizers. J. Therm. Anal. Calorim. 2018, 131(1): 595-600.
  • [14] Provatas, A. Energetic Plasticizer Migration Studies. Energ. Mater. 2003, 21(4): 237-245.
  • [15] Bodaghi, A.; Shahidzadeh, M. Synthesis and Characterization of New PGN Based Reactive Oligomeric Plasticizers for Glycidyl Azide Polymer. Propellants, Explos., Pyrotech. 2018, 43(4): 364-370.
  • [16] Bhowmik, D.; Sadavarte, V.S.; Pande, Sh.M.; Saraswat, B.S. An Energetic Binder for the Formulation of Advanced Solid Rocket Propellants. Cent. Eur. J. Energ.Mater. 2015, 12(1): 145-158.
  • [17] Zohari, N.; Abrishami, F.; Sheibani, N. A Novel Simple Correlation for Predicting Glass Transition Temperature of Energetic Azido-ester Plasticizers through Molecular Structures. J. Therm. Anal. Calorim. 2017, 127(3): 2243-2251.
  • [18] Kawamoto, A.M.; Diniz, M.F.; Lourenço, V.L.; Takahashi, M.F.K.; Keicher, T.; Krause, H.; Menke, K.; Kempa, P.B. Synthesis and Characterization of GAP/BAMO Copolymers Applied at High Energetic Composite Propellants. J. Aerosp. Technol. Manag. 2010, 2(3): 307-322.
  • [19] Chavez, D.E.; Hiskey, M.A.; Parrish, D. Synthesis of an Energetic Nitrate Ester. Angew. Chem. 2008, 120(43): 8431-8433.
  • [20] Shaojun, Q.; Huiqing, F. An Azido Ester Plasticizer, 1,3‐Di(Azidoacetoxy)‐2,2‐Di(Azidomethyl) Propane (PEAA): Synthesis, Characterization and Thermal Properties. Propellants, Explos., Pyrotech. 2006, 31(3): 205-208.
  • [21] Sanghavi, R.R.; Kamale, P.J.; Shaikh, M.A.; Shelar, S.D.; Kumar, K.S.; Singh, A. HMX based Enhanced Energy LOVA Gun Propellant. J. Hazard. Mater. 2007, 143(2): 532-534.
  • [22] Wingborg, N.; Eldsäter, C. 2,2‐Dinitro‐1,3‐bis‐Nitroxy‐Propane (NPN): A New Energetic Plasticizer. Propellants, Explos., Pyrotech. 2002, 27(6): 314-319.
  • [23] Pant, C.S.; Wagh, R.M.; Nair, J.K.; Gori, G.M.; Venugopalan, S. Synthesis and Characterization of Two Potential Energetic Azido Esters. Propellants, Explos., Pyrotech. 2006, 31(6): 477-481.
  • [24] Atabaki, F.; Keshavarz, M.H.; Bastam, N.N. Synthesis and Investigation of the New Derivatives of Poly(Epichlorohydrin) Containing Energetic Groups. Propellants, Explos., Pyrotech. 2018, 43(1): 83-89.
  • [25] Guo, L.; Ma, X.; Zhang, B.; Wang, Z. Synthesis of Polyether Imidazole Ionic Liquid and Its Modification on Polypropylene Crystal Structure and Mechanical Properties. e-Polymers 2015, 15(1): 33-37.
  • [26] Heitbaum, J. XPS-, Raman-, and IR-Analysis of a Surface Product Formed within the Electrooxidation of Phenylhydrazine. Z. Phys. Chem. 1977, 105(5-6): 307-317.
  • [27] Anoop, N. Energetic Polymers. PhD Thesis, Cochin University of Science and Technology, 2013.
  • [28] Öztürk, T.; Ayyıldız, H.; Meyvacı, E.; Göktaş, M. Synthesis and Characterization of Poly(Epichlorohydrin-Graft-Ethylene Glycol) Graft Copolymers by “Click” Chemistry. Karaelmas Sci. Eng. J. 2017, 7(1): 47-54.
  • [29] Huang, T.; Jin, B.; Peng, R.F.; Chu, Sh.J. Synthesis and Characterization of a New Energetic Plasticizer: Acyl-terminated GAP. Int. J. Polym. Anal. Charact. 2014, 19(6): 522-531.
Uwagi
Opracowanie rekordu ze środków MNiSW, umowa Nr 461252 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2021).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-c14bdd05-fb64-49c9-900b-ff86c541d4ae
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