Progress in Chemistry

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Azido Energetic Plasticizers for Gun and Rocket Propellants

Baodong Zhao, Fulei Gao, Yinglei Wang, Yajing Liu, Bin Chen, Yongfei Pan

Progress in Chemistry, 2019, 31(2/3): 475-490. DOI: 10.7536/PC180732

Properties	TMETA^[24]	BDAP1^[28]	ButBAMP^[30]	DAE-4^[34]	DAENP^[38]	DADFAH^[75]	DIANP^[58]
N /%^a	64.62	51.83	25.75	35.16	49.23	20.00	55.98
OB /%^b	-118.86	-118.41	-161.79	-108.45	-100.41	-68.52	-79.94
ρ /g·cm^{-3 c}	1.18	-	1.09	-	1.32	1.34	1.33
T_d/℃^d	252.7	230.4	226	242.50	245.50	195.2	241.87
T_g /℃^e	-	-101.3	-95	-57.9	-96.73	-111.2	-38
Δ H_r /J·g^{-1 f}	-	-	-	1876	2056.13	-	-
Δ H_f /kJ·mol^{-1 g}	-	848.08	-	119.00	464.00	-	539.2
IS /cm^h	31.6^j	-	> 40^k	165^j	> 170^j	5.9^l	20.28^l
FS /Nⁱ	20%^m	> 360	> 360	40	> 36ⁿ	100%°	26%°

Table 6 Comparison of the properties of representative azido plasticizers^{[24, 28, 30, 34, 38, 58, 75]}

Other figure/table from this article

Fig. 1 Structures and abbreviations of representative azido plasticizers
Fig. 2 Synthetic route for TMETA^[24]
Fig. 3 Synthetic routes for plasticizers BDPF and DAEF^{[26, 27]}
Fig. 4 Structures of plasticizers BDAPs^[28]
Table 1 Properties of plasticizers BDAPs^[28]
Table 2 Plasticizing performance of BDAPs on binders GAP and GAP Polyurethane^[28]
Fig. 5 Synthetic route for plasticizer TAA^[29]
Table 3 Properties of plasticizers AcBAMP, ProBAMP, ButBAMP and DEGBAA^[30]
Fig. 6 Synthetic route for plasticizers BAMPs^[30]
Fig. 7 Structures of plasticizers BAAEM and BAAEG^{[31, 32]}
Fig. 8 Synthetic route for plasticizers [G-1]-(N₃)₆ and [G-1]-(N₃)₈^[33]
Fig. 9 Structures of plasticizers DAEs^[34]
Table 4 Properties of plasticizers DAEs^[34]
Fig. 10 Structures of plasticizers AEs^[35]
Table 5 Plasticizing performance of plasticizers AEs on GAP and PolyBAMO^[35]
Fig. 11 Synthetic route for NMPA^[36]
Fig. 12 Synthetic route for DAENP^[38]
Fig. 13 Synthetic route for DAMNP and ENPEA^{[41, 42]}
Fig. 14 Synthetic route for plasticizer DPTB^[44]
Fig. 15 Synthetic route for compound DABAMDB^[46]
Fig. 16 Synthetic route for DADNH and BAADNH^{[49, 50]}
Fig. 17 Synthetic route for DIANP and PNAN^{[51~54, 58, 61]}
Fig. 18 Synthetic route for DANP and DATH from Urotropine^{[64, 69]}
Fig. 19 Synthetic route for plasticizer DANP from urea^[65]
Fig. 20 Synthetic route for AENAs^[70]
Fig. 21 Synthetic route for plasticizer ADFE^[71]
Fig. 22 Synthetic route for plasticizer DADFAH^[75]
Fig. 23 Synthetic route for GAPA-1 and GAPA-2^[76]
Fig. 24 Synthetic route for AATGAP^[77]
Fig. 25 Synthetic route for GAPA-n^[78]
Fig. 26 Synthetic route for TNB-GAP^[79]
Fig. 27 Synthetic route for PHPGN, PAPGN and PMPGN^[80]

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