Methods of producing energetic polymers, energetic binders, and energetic compositions

Patent metadata

Field	Value
Publication number	US-10696786-B2
Application number	US-201414567334-A
Country	US
Kind code	B2
Filing date	Dec 11, 2014
Priority date	Dec 11, 2014
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

A method of producing an energetic polymer comprises reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative to produce a geminal dinitro polyester. A method of producing an energetic binder, and a method of producing an energetic composition are also described.

First claim

What is claimed is:

1. A method of producing an energetic polymer, comprising:
combining, under a nitrogen gas atmosphere, a mixture consisting of a diacid chloride and an organic solvent with a solution consisting of an amine and the organic solvent to react the diacid chloride with the amine and form an acyl ammonium salt; and
reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to produce a geminal dinitro polyester.

2. The method of claim 1 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt comprises reacting the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt in the presence of at least one acid scavenger.

3. The method of claim 2 , wherein reacting the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt in the presence of at least one acid scavenger comprises reacting the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt in the presence of pyridine.

4. The method of claim 2 , wherein reacting the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt in the presence of at least one acid scavenger comprises:
combining the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to form a reaction solution; and
introducing the at least one acid scavenger into the reaction solution.

5. The method of claim 1 , wherein reacting the 2,2-dinitro-1,3-propanediol with the acyl ammonium salt in the presence of at least one acid scavenger comprises:
combining the 2,2-dinitro-1,3-propanediol with the at least one acid scavenger to form a mixture; and
introducing the acyl ammonium salt into the mixture.

6. The method of claim 1 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt comprises introducing the 2,2-dinitro-1,3-propanediol in molar excess to the acyl ammonium salt to produce the geminal dinitro polyester, the geminal dinitro polyester exhibiting energetic, hydroxyl-terminated reactive capping groups.

7. The method of claim 1 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt comprises:
introducing the acyl ammonium salt in molar excess to the 2,2-dinitro-1,3-propanediol to form an acid-halide-terminated geminal dinitro polyester; and
hydrolyzing the acid-halide-terminated geminal dinitro polyester to produce the geminal dinitro polyester, the geminal dinitro polyester exhibiting carboxyl-terminated reactive capping groups.

8. The method of claim 1 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt comprises:
introducing the acyl ammonium salt in molar excess to the 2,2-dinitro-1,3-propanediol to produce an acid-halide-terminated geminal dinitro polyester; and
reacting the acid-halide-terminated geminal dinitro polyester with at least one non-energetic diol to produce the geminal dinitro polyester, the geminal dinitro polyester exhibiting non-energetic, hydroxyl-terminated reactive capping groups.

9. The method of claim 8 , further comprising introducing at least one acid scavenger to the acid-halide-terminated geminal dinitro polyester prior to reacting the acid-halide-terminated geminal dinitro polyester with the non-energetic diol.

10. A method of producing an energetic binder, comprising:
combining, under a nitrogen gas atmosphere, a mixture consisting of a diacid chloride and an organic solvent with a solution consisting of an amine and the organic solvent to react the diacid chloride with the amine and form an acyl ammonium salt; and
reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to produce a geminal dinitro polyester; and
crosslinking polymer chains of the geminal dinitro polyester.

11. The method of claim 10 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to produce the geminal dinitro polyester comprises forming the geminal dinitro polyester to exhibit hydroxyl-terminated reactive capping groups.

12. The method of claim 11 , wherein crosslinking polymer chains of the geminal dinitro polyester comprises reacting the geminal dinitro polyester with at least one polyisocyanate to produce a geminal dinitro polyurethane.

13. The method of claim 11 , wherein forming the geminal dinitro polyester to exhibit hydroxyl-terminated reactive capping groups comprises forming the geminal dinitro polyester to exhibit non-energetic, hydroxyl-terminated reactive capping groups.

14. The method of claim 10 , wherein reacting 2,2-dinitro-1,3-propanediol 1 with the acyl ammonium salt to produce the geminal dinitro polyester comprises forming the geminal dinitro polyester to exhibit carboxyl-terminated reactive capping groups.

15. The method of claim 14 , wherein crosslinking polymer chains of the geminal dinitro polyester comprises reacting the geminal dinitro polyester with at least one polyepoxide to produce a crosslinked geminal dinitro polyester.

16. A method of producing an energetic composition, comprising:
combining, under a nitrogen gas atmosphere, a mixture consisting of a diacid chloride and an organic solvent with a solution consisting of an amine and the organic solvent to react the diacid chloride with the amine and form an acyl ammonium salt; and
reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to produce a geminal dinitro polyester;
crosslinking polymer chains of the geminal dinitro polyester to produce an energetic binder; and
combining the energetic binder with at least one additional energetic material.

17. The method of claim 16 , wherein combining the energetic binder with at least one additional energetic material comprises combining the energetic binder with at least one of a crystalline form and a non-crystalline form of at least one of RDX, HMX, TNT, TATB, NTO, TEX, FOX-7, CL-20, NQ, TNAZ, FOX-12, HNS, AND, DAAOF, and TAGzT.

18. The method of claim 1 , wherein reacting 2,2-dinitro-1,3-propanediol with the acyl ammonium salt to produce a geminal dinitro polyester comprises reacting the 2,2-dinitro-1,3-propanediol with an acyl ammonium salt derived from sebacoyl chloride.

19. The method of claim 1 , further comprising selecting the diacid chloride from the group consisting of oxalyl chloride, glutaryl chloride, adipoyl chloride, suberoyl chloride, azelaoyl chloride, and diglycolyl chloride.

20. The method of claim 1 , wherein a diacid chloride amine to form an acyl ammonium salt comprises selecting the amine from the group consisting of triethylene diamine and triethylamine.

21. The method of claim 1 , further comprising selecting the organic solvent to comprise a non-carbonyl-containing polar aprotic organic solvent.

22. The method of claim 8 , further comprising selecting the at least one non-energetic diol from the group consisting of 2,2-dimethyl-1,3-propanediol, ethylene glycol, propylene glycol, tetramethylene glycol, diethylene glycol, hexamethylene glycol, octamethylene glycol, decamethylene glycol, cyclopentylene-1,3-diol, cyclohexylene-1,2-diol, cyclohexylene-1,3-diol, cyclohexylene-1,4-diol, catechol, resorcinol, quinol, 1-methyl-2,4-benzenediol, 2-methyl-1,3-naphthalenediol, 2,4-toluenediol, xylylene-1,3-diol, 1,5 naphthalenedimethanol, 2-ethyl-1-phenyl-3-butene-1,2-diol, 2,2 di(4-hydroxyphenyl) propane, and triethylene glycol.

Assignees

• Northrop Grumman Innovation Systems Inc

Inventors

• Straessler Nicholas A
• Killpack Michael O
• Doll Daniel W

Classifications

• C08G18/463 Primary

  containing nitro groups · CPC title

• C06B45/105

  The resin being a polymer bearing energetic groups or containing a soluble organic explosive · CPC title

• C08G63/685

  containing nitrogen · CPC title

• C08G63/16 Primary

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C06B25/00

  Compositions containing a nitrated organic compound · CPC title