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化学进展 2019, Vol. 31 Issue (2/3): 475-490 DOI: 10.7536/PC180732 前一篇   

• •

火药用叠氮含能增塑剂

赵宝东, 高福磊, 汪营磊**(), 刘亚静, 陈斌, 潘永飞   

  1. 西安近代化学研究所 西安 710065
  • 收稿日期:2018-07-23 出版日期:2019-02-15 发布日期:2018-10-15
  • 通讯作者: 汪营磊
  • 基金资助:
    国家自然科学基金项目(21173163); 国家自然科学基金项目(21875185)
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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:2018-07-23 Online:2019-02-15 Published:2018-10-15
  • Contact: Yinglei Wang
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(21173163); National Natural Science Foundation of China(21875185)

叠氮增塑剂具有较好热稳定性、较低玻璃化转变温度、钝感及与黏合剂物理化学相容性好等特点,在低易损性、低特征信号推进剂和发射药中有着广阔的应用前景。本文从叠氮增塑剂的合成、表征、性能及应用等方面对近年来取得的研究进展进行了综述,梳理了叠氮增塑剂研究中存在的问题,指出了今后叠氮增塑剂在结构设计、合成、制备工艺、表征及应用等方面的几个潜在发展方向,以期为含能材料合成、配方应用及性能表征等相关的研究者提供参考。

关键词： 含能材料, 叠氮增塑剂, 热稳定性, 玻璃化转变温度, 相容性

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
()
图1 典型叠氮增塑剂的结构及缩写
Fig. 1 Structures and abbreviations of representative azido plasticizers
图2 TMETA的合成路线 [24]
Fig. 2 Synthetic route for TMETA [24]
图3 增塑剂BDPF和DAEF的合成路线 [26, 27]
Fig. 3 Synthetic routes for plasticizers BDPF and DAEF [26, 27]
图4 增塑剂BDAPs的结构 [28]
Fig. 4 Structures of plasticizers BDAPs [28]
表1 增塑剂BDAPs的性能[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
表2 BDAPs对黏合剂GAP和GAP聚亚胺酯的增塑效果[28]
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
图5 增塑剂TAA的合成路线 [29]
Fig. 5 Synthetic route for plasticizer TAA [29]
表3 增塑剂AcBAMP、ProBAMP、ButBAMP和DEGBAA的性能 [30]
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
图6 增塑剂BAMPs的合成路线 [30]
Fig. 6 Synthetic route for plasticizers BAMPs [30]
图7 增塑剂BAAEM和BAAEG的结构 [31, 32]
Fig. 7 Structures of plasticizers BAAEM and BAAEG[31, 32]
图8 增塑剂 [G-1]-(N3)6 和 [G-1]-(N3)8的合成路线 [33]
Fig. 8 Synthetic route for plasticizers [G-1]-(N3)6 and [G-1]-(N3)8 [33]
图9 增塑剂DAEs的结构 [34]
Fig. 9 Structures of plasticizers DAEs [34]
表4 增塑剂DAEs的性能[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
图10 增塑剂AEs的结构 [35]
Fig. 10 Structures of plasticizers AEs [35]
表5 增塑剂AEs对GAP和PolyBAMO的增塑效果[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
图11 NMPA的合成路线 [36]
Fig. 11 Synthetic route for NMPA [36]
图12 DAENP的合成路线 [38]
Fig. 12 Synthetic route for DAENP [38]
图13 DAMNP和ENPEA的合成路线 [41, 42]
Fig. 13 Synthetic route for DAMNP and ENPEA [41, 42]
图14 增塑剂DPTB的合成路线 [44]
Fig. 14 Synthetic route for plasticizer DPTB [44]
图15 化合物DABAMDB的合成路线 [46]
Fig. 15 Synthetic route for compound DABAMDB [46]
图16 DADNH和BAADNH的合成路线 [49, 50]
Fig. 16 Synthetic route for DADNH and BAADNH [49, 50]
图17 DIANP和PNAN的合成路线 [51~54, 58, 61]
Fig. 17 Synthetic route for DIANP and PNAN [51~54, 58, 61]
图18 由乌洛托品制备DANP和DATH的合成路线 [64, 69]
Fig. 18 Synthetic route for DANP and DATH from Urotropine [64, 69]
图19 由尿素制备增塑剂DANP的合成路线 [65]
Fig. 19 Synthetic route for plasticizer DANP from urea [65]
图20 AENAs的合成路线 [70]
Fig. 20 Synthetic route for AENAs [70]
图21 增塑剂ADFE的合成路线[71]
Fig. 21 Synthetic route for plasticizer ADFE [71]
图22 增塑剂DADFAH的合成路线 [75]
Fig. 22 Synthetic route for plasticizer DADFAH [75]
图23 GAPA-1和GAPA-2的合成路线 [76]
Fig. 23 Synthetic route for GAPA-1 and GAPA-2 [76]
图24 AATGAP的合成路线 [77]
Fig. 24 Synthetic route for AATGAP [77]
图25 GAPA-n的合成路线 [78]
Fig. 25 Synthetic route for GAPA-n [78]
图26 TNB-GAP的合成路线[79]
Fig. 26 Synthetic route for TNB-GAP[79]
图27 PHPGN、PAPGN和PMPGN的合成路线[80]
Fig. 27 Synthetic route for PHPGN, PAPGN and PMPGN [80]
表6 叠氮增塑剂典型代表的性能对比 [24, 28, 30, 34, 38, 58, 75]
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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摘要

火药用叠氮含能增塑剂