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

Patent metadata

Field	Value
Publication number	US-2016168317-A1
Application number	US-201414567334-A
Country	US
Kind code	A1
Filing date	Dec 11, 2014
Priority date	Dec 11, 2014
Publication date	Jun 16, 2016
Grant date	—

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 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.

2 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises reacting 2,2-dinitro-1,3-propanediol with the at least one of the diacid halide and the diacid halide derivative.

3 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises reacting the at least one energetic diol with at least one diacid chloride.

4 . The method of claim 3 , wherein reacting the at least one energetic diol with at least one diacid chloride comprises reacting the at least one energetic diol with at least one of oxalyl chloride, malonyl chloride, succinyl chloride, glutaryl chloride, adipoyl chloride, pimeloyl chloride, suberoyl chloride, azelaoyl chloride, diglycolyl chloride, and sebacoyl chloride.

5 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises:
reacting at least one diacid chloride with at least one amine to form an acyl ammonium salt; and reacting the at least one energetic diol with the acyl ammonium salt.

6 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises reacting the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative in the presence of an organic solvent.

6 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises reacting the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative in the presence of at least one acid scavenger.

7 . The method of claim 6 , wherein reacting the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative in the presence of at least one acid scavenger comprises reacting the at least one energetic diol with at least one diacid halide in the presence of pyridine.

8 . The method of claim 6 , wherein reacting the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative in the presence of at least one acid scavenger comprises:
combining the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative to form a reaction solution; and introducing the at least one acid scavenger into the reaction solution.

9 . The method of claim 1 , wherein reacting the at least one energetic diol with the at least one of the diacid halide and the diacid halide derivative in the presence of at least one acid scavenger comprises:
combining the at least one energetic diol with the at least one acid scavenger to form a mixture; and introducing the at least one of the diacid halide and the diacid halide derivative into the mixture.

10 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises introducing the at least one energetic diol in molar excess to the diacid halide to produce the geminal dinitro polyester, the geminal dinitro polyester exhibiting energetic, hydroxyl-terminated reactive capping groups.

11 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises:
introducing the diacid halide in molar excess to the at least one energetic diol 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.

12 . The method of claim 1 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises:
introducing the diacid halide in molar excess to the at least one energetic diol 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.

13 . The method of claim 12 , 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.

14 . A method of producing an energetic binder, comprising:
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; and crosslinking polymer chains of the geminal dinitro polyester.

15 . The method of claim 14 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative to produce the geminal dinitro polyester comprises forming the geminal dinitro polyester to exhibit hydroxyl-terminated reactive capping groups.

16 . The method of claim 15 , 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.

17 . The method of claim 15 , 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.

18 . The method of claim 14 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative to produce the geminal dinitro polyester comprises forming the geminal dinitro polyester to exhibit carboxyl-terminated reactive capping groups.

19 . The method of claim 18 , 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.

20 . A method of producing an energetic composition, comprising:
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; 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.

21 . The method of claim 20 , wherein reacting at least one energetic diol with at least one of a diacid halide and a diacid halide derivative comprises reacting 2,2-dinitro-1,3-propanediol with sebacoyl chloride.

22 . The method of claim 21 , wherein reacting 2,2-dinitro-1,3-propanediol with sebacoyl chloride comprises introducing the 2,2-dinitro-1,3-propanediol in molar excess relative to the sebacoyl chloride.

23 . The method of claim 22 , wherein crosslinking polymer chains of the geminal dinitro polyester comprises reacting the geminal dinitro polyester with a diisocyanate.

24 . The method of claim 21

Assignees

• Orbital Atk Inc

Inventors

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

Classifications

• C08G18/463 Primary

  containing nitro groups · CPC title

• C06B25/04

  the nitrated compound being an aromatic · CPC title

• C06B25/34

  the compound being a nitrated acyclic, alicyclic or heterocyclic amine · CPC title

• C08G63/916

  Dicarboxylic acids and dihydroxy compounds · CPC title

• C06B25/00

  Compositions containing a nitrated organic compound · CPC title