Organic compounds -- part of the class 532-570 series – Organic compounds – Azides
Reexamination Certificate
2000-09-15
2001-04-17
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azides
C568S012000, C149S108600, C149S121000
Reexamination Certificate
active
06218554
ABSTRACT:
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
The invention described herein may be made, used, or licensed by or for the United States Government for Governmental purposes without the payment of any royalties thereon or therefor.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel cyclotetraphosphazene compound and a method of producing the same. In particular, the present invention relates to 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, which has shown to be useful as an energetic composition.
2. Description of Related Art
Many energetic compositions are environmentally objectionable. As an example, prior art percussion primers typically use lead azide, lead styphnate, antimony sulfide, barium nitrate, mercury fulmanate and other materials containing heavy metals that are known to contribute to environmental pollution during manufacturing and use. Firing of small arms, especially in indoor firing ranges, releases clouds of hazardous gases in addition to increased contamination of the soil and ground water.
The need for alternative energetic compositions that are more environmentally friendly has been felt for some time, and several attempts have been made to provide such a compound.
U.S. Pat. No. 5,717,159 issued to Dixon, Martin, and Thompson on Feb. 10, 1998. This reference is entitled Lead-Free Percussion Primer Mixes Based on Metastable Interstitial Composite (MIC) Technology, and discloses a mixture of aluminum powder having an outer coating of aluminum oxide and either molybdenum trioxide or polytetrafluoroethylene.
U.S. Pat. No. 5,993,577 issued to Erickson, Melberg and Sandstrom on Nov. 30, 1999. This reference is entitled Lead-Free, Heavy-Metal-Free Rim-Fire Priming Composition, and discloses a combination of diazodinitrophenol, tetracene, ground glass, and a lead-free, heavy-metal-free oxidizer, together with a binder and a dye.
Cyclotriphosphazenes have been reported as energetic compounds in
Novel Spiro Substituted Cyclotriphosphazenes Incorporating Ethylenedinitramine Units
, Dave, et al., Phosphorus, Sulfur, and Silicon, 1994, vol. 90, pp. 175-184, and in
Synthesis Of Ethylenedinitramine Deriatives Of Fluorocyclotriphosphazenes,
Forohar, et al., Phosphorus, Sulfur, and Silicon, 1995, vol. 101, pp. 161-166.
BRIEF SUMMARY OF THE INVENTION
Objects of the Invention
It is an object of the present invention to provide an environmentally friendly energetic compound.
The other objects, features and advantages of the present invention will become more apparent in light of the following detailed description of the preferred embodiment thereof.
SUMMARY OF THE INVENTION
According to the present invention, a novel compound, 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, is disclosed.
According to another embodiment of the present invention, there is disclosed a novel energetic composition comprising 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene.
According to a still further embodiment of the present invention, there is disclosed a method of preparation of 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, which method comprises the steps of:
a. reacting a quantity of octachlorocyclotetraphosphazene with ammonium hydroxide in ether to produce isomers of diaminohexachlorocyclotetraphosphazene;
b. isolating 1,5-diamino-1,3,3,5,7,7-hexachlorocyclotetraphosphazene from the reaction product of step (a);
c. reacting the 1,5-diamino-1,3,3,5,7,7-hexachlorocyclotetraphosphazene with sodium azide in acetone to produce 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene.
DETAILED DESCRIPTION OF THE INVENTION
Phosphazenes are phosphorous-nitrogen ring compounds which have two substituents attached to each phosphorous atom. These substituents can be manipulated to place a variety of different groups on the ring system. Two major types of phosphazenes appear to have commercial use. The first class includes six membered ring cyclotriphosphazenes such as hexachlorocyclotriphosphazene. The second class includes eight membered ring cyclotetraphosphazenes such as octachlorocyclotetraphosphazene.
The present invention comprises a novel cyclotetraphosphazene derived from octachlorocyclotetraphosphazene, which is commercially available from Phosphazene Custom Synthesis, Inc., 2820 East College Avenue, Suite N, State College, Pa. 16801. The novel compound of the present invention, 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, was synthesized and identified as a new class of environmentally friendly energetic compositions. It has demonstrated positive experimental results for such application.
This novel compound of the present invention, 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, was synthesized from octachlorocyclotetraphosphazene in the following manner. First, a quantity of octachlorocyclotetraphosphazene was reacted with ammonium hydroxide in ether to produce isomers of diaminohexachlorocyclotetraphosphazene. This reaction has been reported in the literature. See, J. K. Fincham, R. A. Shaw, “Phosphorous-Nitrogen Compounds. Part 62”.
Phosphorous, Sulfur, and Silicon,
1990, Vol. 47, p. 109. Then, after isolating 1,5-diamino-1,3,3,5,7,7-hexachlorocyclotetraphosphazene from the reaction products of the first step, the 1,5-diamino-1,3,3,5,7,7-hexachlorocyclotetraphosphazene was reacted with sodium azide in acetone to produce 1,5-diamino-1,3,3,5,7,7-hexaazidocyclotetraphosphazene, which was then obtained from solution.
Differential Scanning Calorimetry (DSC) indicated that the novel compound decomposes violently at two hundred thirty-four degrees Celsius (234° C.).
REFERENCES:
Database Caplus on STN, Acc. No. 1981:408685, Heitsch et al., ‘Fire retardant textiles—cotton treated with amidophosphazene.’ Org. Coat. Plast. Chem. (1979), 41, pp. 97-102 (abstract), 1981.
Dave Paritosh R.
Forohar Farhad
Iyer Sury
Beam Robert
Davis Brian J.
Moran John F.
Richter Johann
Sachs Michael C.
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