IP Library Granted Patent US 8,425,702
Granted Patent B2
US 8,425,702 · App. 13/177,263 · Granted Apr 23, 2013

Precursor of an explosive composition including at least one ionic liquid and a method of desensitizing an explosive composition

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Quick Facts
Patent No.
US 8,425,702
App. No.
13/177,263
Granted
Apr 23, 2013
Kind
B2
Abstract

An ionic liquid is disclosed. A precursor composition that comprises at least one ionic liquid and at least one energetic material is also disclosed, as is a method of synthesizing an ionic liquid and a method of desensitizing an explosive composition.

Claims (20)

1. A precursor composition of an explosive composition comprising:

at least one ionic liquid and at least one energetic material, wherein the at least one ionic liquid comprises at least one cation and at least one anion, wherein the at least one cation comprises at least one ion selected from the group consisting of ammonium, guanidinium, aminoguanidinium, diaminoguanidinium, triaminoguanidinium, hydroxylammonium, hydrazinium, urea, guanylurea, guanizinium, triazanium, triazenium, alkyl ammonium, dialkyl ammonium, trialkyl ammonium, triazolium, 1,2,4-triazolium, aminotriazolium, 3-amino-1,2,4-triazolium, 4-amino-1,2,4-triazolium, 3,5-diamino-1,2,4-triazolium, tetrazolium, diaminotetrazolium, imidazolium, alkyl imidazolium, morpholinium, pyridinium, a quaternary ammonium compound, and a quaternary phosphonium compound and the at least one anion comprises at least one ion selected from the group consisting of hexafluoroglutarate, trifluoroacetate, acetate, lactate, gluconate, formate, tetrazolate, aminotetrazolate, 5-aminotetrazolate, oxalate, succinate, tetrafluorosuccinate, glycolate, L-tartrate, DL-tartrate, DL-malate, maleate, malonate, nitrilotriacetate, mucobromate, tetrafluoroborate, alkylsulfate, alkylphosphate, bis-trifluorosulfonimide, triflate, tosylate, hexafluorophosphate, and a boron-containing compound.

2. The precursor composition of claim 1 , wherein the at least one ionic liquid comprises guanidinium hexafluoroglutarate, aminoguanidinium hexafluoroglutarate, bis(aminoguanidinium) hexafluoroglutarate, bis(hydroxylammonium) hexafluoroglutarate, bis(hydrazinium) hexafluoroglutarate, guanidinium trifluoroacetate, aminoguanidinium trifluoroacetate, triaminoguanidinium trifluoroacetate, hydrazinium trifluoroacetate, 1,2,4-triazolium trifluoroacetate, 3-amino-1,2,4-triazolium trifluoroacetate, 4-amino-1,2,4-triazolium trifluoroacetate, 3,5-diamino-1,2,4-triazolium trifluoroacetate, guanidinium tetrafluorosuccinate, aminoguanidinium tetrafluorosuccinate, guanidinium oxalate, aminoguanidinium oxalate, aminoguanidinium:guanidinium oxalate, bis(guanidinium) malonate, bis(aminoguanidinium) malonate, aminoguanidinium:guanidinium malonate, aminoguanidinium L-tartrate, bis(guanidinium) L-tartrate, bis(aminoguanidinium) L-tartrate, guanidinium glycolate, aminoguanidinium glycolate, triazolium acetate, tetrazolium acetate, diaminotetrazolium acetate, diaminoguanidinium acetate, triaminoguanidinium acetate, bis(aminoguanidinium) DL-malate, tris(aminoguanidinium) nitrilotriacetate, aminoguanidinium mucobromate, diaminoguanidinium-hydrochloric acid/urea, guanidinium 5-aminotetrazolate, aminoguanidinium 5-aminotetrazolate, diaminoguanidinium 5-aminotetrazolate, triaminoguanidinium 5-aminotetrazolate, and combinations thereof.

3. The precursor composition of claim 1 , wherein the at least one energetic material comprises at least one material selected from the group consisting of dinitrotoluene, trinitrotoluene, cyclotetramethylene tetranitramine, cyclo-1,3,5-trimethylene-2,4,6-trinitramine, hexanitrohexaazaisowurtzitane, triaminotrinitrobenzene, nitrotriazolone, Composition B, 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetra-cyclo[5.5.0.0 5,9 .0 3,11 ]dodecane, 1,3,3-trinitroazetine, and ammonium dinitramide.

4. The precursor composition of claim 1 , wherein the at least one ionic liquid comprises from approximately 13% by weight of a total weight of the precursor composition to approximately 75% by weight of the total weight of the precursor composition.

5. The precursor composition of claim 1 , wherein the at least one energetic material comprises from approximately 25% by weight of a total weight of the precursor composition to approximately 90% by weight of the total weight of the precursor composition.

6. The precursor composition of claim 1 , wherein the at least one ionic liquid has a melting point between approximately 80° C. and approximately 110° C.

7. The precursor composition of claim 1 , further comprising at least one oxidizer selected from the group consisting of ammonium nitrate, ammonium perchlorate, sodium nitrate, potassium nitrate, lithium nitrate, rubidium nitrate, cesium nitrate, lithium perchlorate, sodium perchlorate, potassium perchlorate, rubidium perchlorate, cesium perchlorate, magnesium perchlorate, calcium perchlorate, strontium perchlorate, barium perchlorate, barium peroxide, strontium peroxide, and copper oxide.

8. The precursor composition of claim 1 , further comprising at least one metal or metal-containing compound selected from the group consisting of aluminum, nickel, magnesium, silicon, boron, beryllium, zirconium, hafnium, zinc, tungsten, molybdenum, titanium, aluminum hydride, magnesium hydride, and a borane compound.

9. The precursor composition of claim 1 , further comprising at least one solid ingredient selected from the group consisting of a sugar, processing aid, surfactant, binder, energetic polymer, inert polymer, fluoropolymer, thermal stabilizer, and plasticizer.

10. A method of desensitizing an explosive composition, comprising:

adding at least one energetic material to a melt phase comprising at least one ionic liquid, wherein the at least one ionic liquid comprises at least one cation and at least one anion and wherein the at least one cation comprises at least one ion selected from the group consisting of ammonium, guanidinium, aminoguanidinium, diaminoguanidinium, triaminoguanidinium, hydroxylammonium, hydrazinium, urea, guanylurea, guanizinium, triazanium, triazenium, alkyl ammonium, dialkyl ammonium, trialkyl ammonium, triazolium, 1,2,4-triazolium, aminotriazolium, 3-amino-1,2,4-triazolium, 4-amino-1,2,4-triazolium, 3,5-diamino-1,2,4-triazolium, tetrazolium, diaminotetrazolium, imidazolium, alkyl imidazolium, morpholinium, pyridinium, a quaternary ammonium compound, and a quaternary phosphonium compound and the at least one anion comprises at least one ion selected from the group consisting of hexafluoroglutarate, trifluoroacetate, acetate, lactate, gluconate, formate, tetrazolate, aminotetrazolate, 5-aminotetrazolate, oxalate, succinate, tetrafluorosuccinate, glycolate, L-tartrate, DL-tartrate, DL-malate, maleate, malonate, nitrilotriacetate, mucobromate, tetrafluoroborate, alkylsulfate, alkylphosphate, bis-trifluorosulfonimide, triflate, tosylate, hexafluorophosphate, and a boron-containing compound.

11. The method of claim 10 , wherein adding at least one energetic material to a melt phase comprising at least one ionic liquid comprises adding at least one energetic material selected from the group consisting of dinitrotoluene, trinitrotoluene, cyclotetramethylene tetranitramine, cyclo-1,3,5-trimethylene-2,4,6-trinitramine, hexanitrohexaazaisowurtzitane, triaminotrinitrobenzene, nitrotriazolone, Composition B, 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetra-cyclo[5.5.0.0 5,9 .0 3,11 ]dodecane, 1,3,3-trinitroazetine, and ammonium dinitramide to the melt phase.

12. The method of claim 10 , further comprising adding at least one oxidizer selected from the group consisting of ammonium nitrate, ammonium perchlorate, sodium nitrate, potassium nitrate, lithium nitrate, rubidium nitrate, cesium nitrate, lithium perchlorate, sodium perchlorate, potassium perchlorate, rubidium perchlorate, cesium perchlorate, magnesium perchlorate, calcium perchlorate, strontium perchlorate, barium perchlorate, barium peroxide, strontium peroxide, and copper oxide to the melt phase.

13. The method of claim 10 , further comprising adding at least one metal or metal-containing compound selected from the group consisting of aluminum, nickel, magnesium, silicon, boron, beryllium, zirconium, hafnium, zinc, tungsten, molybdenum, titanium, aluminum hydride, magnesium hydride, and a borane compound to the melt phase.

14. The method of claim 10 , further comprising adding at least one solid ingredient selected from the group consisting of a sugar, processing aid, surfactant, binder, energetic polymer, inert polymer, fluoropolymer, thermal stabilizer, and plasticizer to the melt phase.

15. The precursor composition of claim 3 , wherein the at least one ionic liquid comprises at least one of guanidinium trifluoroacetate and aminoguanidinium trifluoroacetate.

16. The precursor composition of claim 3 , wherein the precursor composition comprises at least one of guanidinium trifluoroacetate and aminoguanidinium trifluoroacetate and at least one of cyclo-1,3,5-trimethylene-2,4,6-trinitramine, cyclotetramethylene tetranitramine, hexanitrohexaazaisowurtzitane, trinitrotoluene, nitrotriazolone, triaminotrinitrobenzene, and 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetra-cyclo[5.5.0.0 5,9 .0 3,11 ]dodecane.

17. The precursor composition of claim 3 , wherein the precursor composition comprises aminoguanidinium trifluoroacetate and cyclo-1,3,5-trimethylene-2,4,6-trinitramine, cyclotetramethylene tetranitramine, or hexanitrohexaazaisowurtzitane.

18. The precursor composition of claim 3 , wherein the at least one ionic liquid has a melting point between approximatel 70° C. and approximately110° C.

Assignments (9)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 8, 2021
From: NORTHROP GRUMMAN INNOVATION SYSTEMS LLC
To: NORTHROP GRUMMAN SYSTEMS CORPORATION
Reel/Frame 055256/0892 →
CHANGE OF NAME Recorded Feb 4, 2021
From: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC.
To: NORTHROP GRUMMAN INNOVATION SYSTEMS LLC
Reel/Frame 055223/0425 →
CHANGE OF NAME Recorded Nov 1, 2018
From: ORBITAL ATK, INC.
To: NORTHROP GRUMMAN INNOVATION SYSTEMS, INC.
Reel/Frame 047400/0381 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jun 6, 2018
From: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
To: ORBITAL ATK, INC.
Reel/Frame 046477/0874 →
CHANGE OF NAME Recorded Nov 28, 2017
From: ALLIANT TECHSYSTEMS INC.
To: ORBITAL ATK, INC.
Reel/Frame 044824/0466 →
RELEASE OF SECURITY INTEREST Recorded Oct 8, 2015
From: BANK OF AMERICA, N.A.
To: ALLIANT TECHSYSTEMS INC.; FEDERAL CARTRIDGE CO.; EAGLE INDUSTRIES UNLIMITED, INC.; AMMUNITION ACCESSORIES, INC.; ORBITAL ATK, INC. (F/K/A ALLIANT TECHSYSTEMS INC.)
Reel/Frame 036816/0624 →
SECURITY AGREEMENT Recorded Sep 30, 2015
From: ORBITAL ATK, INC.; ORBITAL SCIENCES CORPORATION
To: WELLS FARGO BANK, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 036732/0170 →
SECURITY AGREEMENT Recorded Nov 26, 2013
From: ALLIANT TECHSYSTEMS INC.; CALIBER COMPANY; EAGLE INDUSTRIES UNLIMITED, INC.; FEDERAL CARTRIDGE COMPANY; SAVAGE ARMS, INC.; SAVAGE RANGE SYSTEMS, INC.; SAVAGE SPORTS CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 031731/0281 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT SUPPLEMENT Recorded Oct 31, 2011
From: ALLIANT TECHSYSTEMS INC.
To: BANK OF AMERICA, N.A.
Reel/Frame 027151/0658 →