IP Library Granted Patent US 9,914,734
Granted Patent B2
US 9,914,734 · App. 13/264,721 · Granted Mar 13, 2018

Cyclic energetic nitramines desensitized with linear nitramines

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Quick Facts
Patent No.
US 9,914,734
App. No.
13/264,721
Granted
Mar 13, 2018
Kind
B2
Abstract

Propellant compositions containing cyclic nitramines that are susceptible to unintentional detonation are desensitized by the incorporation of a linear nitramine having a backbone containing one to three ethylene groups and one or two nitramine groups.

Claims (25)

1. A low-sensitivity propellant formulation comprising a cyclic nitramine and a linear nitramine, wherein said linear nitramine is a solid energetic material having a melting point within a range of 50° C. to 150° C. and has the formula

wherein:

m is zero or 1;

n is 1 or 2;

R 1 is a member selected from the group consisting of C 1 -C 6 alkyl, nitrato, azido, nitrato-C 1 -C 6 alkyl, and azido-C 1 -C 6 alkyl; and

R 2 is a member selected from the group consisting of C 1 -C 6 alkyl, nitrato, azido, nitrato-(C 1 -C 6 alkyl) and azido-(C 1 -C 6 alkyl);

such that the total number of non-terminal CH 2 CH 2 groups is one, two, or three, and the total number of nitrato groups is one or two; and

wherein said cyclic nitramine has the formula

wherein:

R 2 is a member selected from the group consisting of CH 2 and N—R 4 in which R 4 is a member selected from the group consisting of NO 2 , NO, C(O)CH 3 , CH 2 OCH 3 , CH 2 OC 2 H 5 , H, C 1 -C 4 alkyl, and cyclohexyl;

P is 1 or 2; and

when p is 1, R 3 is a member selected from the group consisting of NO 2 , NO, C(O)CH 3 , CH 2 OCH 3 , CH 2 OC 2 H 5 , H, C 1 -C 4 alkyl, and cyclohexyl, and when p is 2, R 3 is C 1 -C 4 alkylene,

wherein said liner nitramine is N,N′-2,5-diethylethylene dinitramine.

2. A low-sensitivity propellant formulation comprising:

a cyclic nitramine and a linear nitramine, wherein said linear nitramine is a solid energetic material having a melting point within a range of 50° C. to 150° C. and has the formula

wherein:

m is zero or 1; n is 1 or 2;

R 1 is a member selected from the group consisting of C 1 -C 6 alkyl, nitrato, and azido; and

R 2 is a member selected from the group consisting of C 1 -C 6 alkyl, nitrato, and azido,

such that the total number of non-terminal CH 2 CH 2 groups is one, two, or three, and the total number of nitrato groups is one or two; and

wherein said cyclic nitramine has the formula

wherein:

R 2 is a member selected from the group consisting of CH 2 and N—R 4 in which R 4 is a member selected from the group consisting of NO 2 , NO, C(O)CH 3 , CH 2 OCH 3 , CH 2 OC 2 H 5 , H, C 1 -C 4 alkyl, and cyclohexyl;

P is 1 or 2; and

when p is 1, R 3 is a member selected from the group consisting of NO 2 , NO, C(O)CH 3 , CH 2 OCH 3 , CH 2 OC 2 H 5 H, C 1 -C 4 alkyl, and cyclohexyl, and when p is 2, R 3 is C 1 -C 4 alkylene.

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 28, 2023
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: AEROJET ROCKETDYNE, INC.
Reel/Frame 064424/0109 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2016
From: U.S. BANK NATIONAL ASSOCIATION
To: AEROJET ROCKETDYNE, INC. (F/K/A AEROJET-GENERAL CORPORATION)
Reel/Frame 039594/0887 →
NOTICE OF GRANT OF SECURITY INTEREST IN PATENTS Recorded Jun 17, 2016
From: AEROJET ROCKETDYNE, INC., SUCCESSOR-IN-INTEREST TO RPW ACQUISITION LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 039197/0125 →
MERGER Recorded Sep 5, 2013
From: AEROJET-GENERAL CORPORATION
To: AEROJET ROCKETDYNE, INC.
Reel/Frame 031147/0333 →