Energetic triazolium salts

• US 6,509,473 B1
• Filed: 10/16/2000
• Issued: 01/21/2003
• Est. Priority Date: 10/16/2000
• Status: Expired due to Fees

• Current Assignee: Air Force Government of The United States of America As Represented By The Secretary
• Original Assignee: United States Of America As Represented By The Secretary Of The Air Force
• Inventors: Drake, Greg W.
• Primary Examiner(s): Ramsuer, Robert W.
• Application Number:
  US09/688,909
• Time in Patent Office: 827 Days
• Field of Search: 548/262.2, 548/264.8, 548/265.2, 548/265.6, 149/92
• US Class Current: 548/262.2
• CPC Class Codes: C06B 25/34 the compound being a nitrated acyclic, alicyclic or heterocyclic amine
• CPC Class Codes: C06B 43/00 Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
• CPC Class Codes: C07D 249/08 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 249/14 Nitrogen atoms

Abstract

New energetic salts of 1,2,4-triazole; 3,4,5-triamino-1,2,4-triazole and of 4-amino 1,2,4-triazole were synthesized, characterized and their thermal and safety properties evaluated as possible new propellant ingredients. Energetic anions, including the nitrate anion, NO₃, the perchlorate anion, ClO₄, & the dinitramide anion, N(NO₂)₂, were paired with the protonated heterocycles through facile, high yield synthetic routes to give crystalline, energetic salts. Using such a heterocycle system, either 1,2,4-triazole; 3,4,5-triamino-1,2,4-triazole or 4-amino 1,2,4-triazole, a new family of salts were synthesized through the direct reaction of the heterocycle with the corresponding acid form of the desired anion. These reactions were carried out in commonly available polar solvents, and at ambient temperatures, to give high purity, high yield products. All of the salts which were synthesized, were put through thermal stability tests and through impact testing, to reveal a robust family of new insensitive materials, suitable as new energetic propellant ingredients.

Claims

1. A method for making energetic triazole salts comprising, reacting the following:

where R and R′

are H or NH₂, except that when R′

=H, R=H; and

X⁻

is NO₃⁻

;

ClO₄⁻

;

or N(NO₂)₂⁻

.

2. The method of claim 1 wherein:

3. The method of claim 1 wherein:

4. The method of claim 1 wherein:

5. A triazole salt of the formula:

where R and R′

are H or NH₂, except that when R′

=H, R=H; and

X⁻

is NO₃⁻

, ClO₄⁻

, or N(NO₂)₂⁻

.

6. A triazole salt of the formula:

where X⁻

is as stated in claim 5.

7. A triazole salt of the formula:

where X⁻

is as stated in claim 5.

8. A triazole salt of the formula:

where X⁻

is as stated in claim 5.

9. A method of gas generating comprising employing the salt of claim 5 in a gas generating system.