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

Azido Energetic Plasticizers for Gun and Rocket Propellants

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

  1. Xi’an Modern Chemistry Research Institute, Xi’an 710065, China
  • Received: Online: Published:
  • Contact: Yinglei Wang
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(21173163); National Natural Science Foundation of China(21875185)
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With the characteristics of superior thermal stability, lower glass transition temperature, insensitivity and better compatibility with binders, azido plasticizers have vast application prospect in the gun and rocket propellants requiring low vulnerability and low characteristic signal. From the aspects of synthesis, characterization, property and application, recent research progress on azido plasticizers is reviewed in this paper. Then, the existing problems in the research of azido plasticizers are sorted, and some potential development directions on the structure design, synthesis, preparation process, characterization and application are pointed out. This review is expected to benefit the researchers on the synthesis, composition application and property characterization of energetic materials.

Key words: energetic material, azido plasticizer, thermal stability, glass transition temperature, compatibility
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]
Properties BDAP1 BDAP2 BDAP3 BDAP4
N/%a 51.83 47.70 49.68 47.44
OB/%b -118.41 -136.22 -127.68 -117.40
Tonset /℃c 169.8 166.8 169.6 167.6
Tp /℃d 230.4 232.3 232.1 234.9
Tg /℃e -101.3 -92.3 -96.4 -86.0
Δ Hf /kJ·mol-1f 848.08 834.58 804.19 698.19
Δ Hr /J·g-1g 1382.4 1617.2 1616.6 1585.6
FS/Nh > 360 > 360 > 360 > 360
Table 2 Plasticizing performance of BDAPs on binders GAP and GAP Polyurethane[28]
Composition Tg/℃ Composition Tg/℃ Tp/℃
GAP -53.7 GAP Polyurethane -33.8 223.8
GAP+35% BDAP1 -75.3 GAP Polyurethane +10% BDAP1 -43.8 222.0
GAP+35% BDAP2 -69.6 GAP Polyurethane +10% BDAP2 -43.5 221.6
GAP+35% BDAP3 -74.3 GAP Polyurethane +10% BDAP3 -42.6 221.3
GAP+35% BDAP4 -69.4 GAP Polyurethane +10% BDAP4 -42.4 221.5
Fig. 5 Synthetic route for plasticizer TAA [29]
Table 3 Properties of plasticizers AcBAMP, ProBAMP, ButBAMP and DEGBAA [30]
Properties AcBAMP ProBAMP ButBAMP DEGBAA
N /%a 31.10 28.17 25.75 32.80
OB /%b -124 -145 -162 -112
ρ /g·cm-3 c 1.21 1.16 1.09 1.00
Tp/℃d 230 227 226 215
Tg /℃e -80 -86 -95 -63
pCJ /GPaf 7.9 7.2 6.2 4.6
VDet /m·s-1 g 5420 5292 5048 4363
Is /sh 175 171 167 169
IS /Ji > 40 > 40 > 40 > 10
FS /Nj > 360 > 360 > 360 160
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]
Properties DAE-1 DAE-2 DAE-3 DAE-4
N /%a 49.40 43.97 47.71 35.16
Tp/℃b - 240.60 225.40 242.50
Tg /℃c -59.6 -56.6 -42.2 -57.9
Δ Hf /kJ·mol-1 d 329.26 604.48 759.02 119.00
Δ Hr /J·g-1 e - -2395 -1756 -1876
Viscosity /Pa·s 0.78 0.96 0.86 -
IS / cmf 198 161 160 165
FS /Ng 55 39 39 40
Fig. 10 Structures of plasticizers AEs [35]
Table 5 Plasticizing performance of plasticizers AEs on GAP and PolyBAMO[35]
Composition Tg /℃ Composition Tg /℃
GAP -49.78 PolyBAMO -53.77
AE-2 -42.24 AE-8 -41.01
AE-2+GAP -38.82 AE-8+GAP -50.25
AE-2+PolyBAMO -48.22 AE-8+PolyBAMO -54.71
AE-3 -75.97 AE-10 -67.49
AE-3+GAP -53.90 AE-10+GAP -52.49
AE-3+PolyBAMO -59.75 AE-10+PolyBAMO -56.09
AE-4 -34.38 AE-11 -55.66
AE-4+GAP -53.90 AE-11+GAP -51.30
AE-4+PolyBAMO -59.75 AE-11+PolyBAMO -55.38
AE-5 -52.25 AE-12 -45.99
AE-5+GAP -50.11 AE-12+GAP -49.47
AE-5+PolyBAMO -53.60 AE-12+PolyBAMO -53.93
AE-6 -55.48 AE-13 -20.84
AE-6+GAP -50.11 AE-13+GAP -52.98
AE-6+PolyBAMO -53.60 AE-13+PolyBAMO -47.67
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]
Table 6 Comparison of the properties of representative azido plasticizers [24, 28, 30, 34, 38, 58, 75]
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
Td/℃d 252.7 230.4 226 242.50 245.50 195.2 241.87
Tg /℃e - -101.3 -95 -57.9 -96.73 -111.2 -38
Δ Hr /J·g-1 f - - - 1876 2056.13 - -
Δ Hf /kJ·mol-1 g - 848.08 - 119.00 464.00 - 539.2
IS /cmh 31.6j - > 40k 165j > 170j 5.9l 20.28l
FS /Ni 20%m > 360 > 360 40 > 36n 100%° 26%°
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