Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
1997-05-16
2002-10-29
Coleman, Brenda (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C540S556000, C149S092000
Reexamination Certificate
active
06472525
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of The Invention
The present invention relates to an acyl group-containing hexaazaisowurtzitane derivative, and a method for producing the same.
The acyl group-containing hexaazaisowurtzitane derivative of the present invention contains an N—A group (wherein A represents an acyl group) and optionally an N—H group in high concentration, wherein each of the N—A group and the N—H group can be converted to an N—NO
2
group by various nitration methods.
Therefore, the acyl group-containing hexaazaisowurtzitane derivative of the present invention is useful as a precursor of a polynitrohexaazaisowurtzitane derivative which can be used not only as a material for explosives but also as an additive for propellants and explosives. More specifically, a polynitrohexaazaisowurtzitane derivative can be advantageously used as an additive for improving various properties (such as mechanical properties, detonation velocity, detonation pressure, burning rate, pressure exponent, sensitivity, and heat resistance) of propellants and explosives. In addition, hexanitrohexaazaisowurtzitane (hereinafter referred to simply as “HNW”), which is a typical example of the polynitrohexaazaisowurzitan derivative, has been expected to be a promising material for the next-generation high performance explosives. As mentioned above, the acyl group-containing hexaazaisowurtzitane derivative of the present invention is useful as a precursor of such a valuable polynitrohexaazaisowurzitane derivative.
Further, the acyl group-containing hexaazaisowurtzitane derivative of the present invention can be advantageously used, by virtue of the reactivity of each of the N—A group (wherein A represents an acyl group) and the N—H group which are contained therein, for producing a highly polar polymer containing acyl groups in the main and/or side chain thereof in high concentration. This highly polar polymer is useful not only as a highly hydrophilic polymer but also as a highly dielectric polymer.
Still further, the acyl group-containing hexaazaisowurtzitane derivative of the present invention can be advantageously used as a polyfunctional crosslinking agent by virtue of the reactivity of the derivative.
Furthermore, the acyl group-containing hexaazaisowurtzitane derivative of the present invention can also be used as various types of additives, such as a polymer modifier and the like.
2. Prior Art
In addition to the above-mentioned HNW, conventionally known compounds, which have the same hexaazaisowurtzitane (hereinafter referred to simply as “W”) skeleton as in the acyl group-containing hexaazaisowurtzitane derivative of the present invention, include the following:
(1) hexakis(arylmethyl)hexaazaisowurtzitane (hereinafter referred to simply as “HBW”);
(2) tetraacetyldibenzylhexaazaisowurtzitane (hereinafter referred to simply as “TADBW”); and
(3) hexaazaisowurtzitane having a trimethylsilyl-ethyloxycarbonyl group (hereinafter referred to simply as “HCW”) (see Unexamined Japanese Patent Application Laid-Open Specification No. 6-321962).
It is known that HBW can be obtained by a condensation reaction of various arylmethylamines with glyoxal [see J. Org. Chem., vol. 55, 1459-1466 (1990)].
It has been reported that TADBW is useful as a material for producing explosives [see The Militarily Critical Technologies List, Office of the Under Secretary of Defense for Acquisition, 12-22, October (1992)]. However, this reference neither describes a method for converting TADBW to an explosive, the chemical structure of such an explosive obtained from TADBW nor a method for producing TADBW itself.
The properties of HNW, which has been expected to be a promising material for high performance explosives as mentioned above, are described in International Symposium on Energetic Materials Technology, PROCEEDINGS, SEPTEMBER 24-27, 76-81 (1995): COMBUSTION AND FLAME 87, 145-151 (1991) and the like, but a method for producing HNW has not been reported in any literature.
Previously, with a view toward developing a method for producing a polynitrohexaazaisowurtzitane derivative, such as HNW, the present inventors tried to nitrate HBW and TADBW under various nitration conditions. However, it was impossible to obtain a satisfactory amount of a polynitrohexaazaisowurtzitane derivative. Further, HBW and TADBW have a benzyl group, so that, when HBW or TADBW is subjected to nitration, nitroaromatic compounds having high affinity for various nitro compounds are inevitably produced as a by-product. As a result, it is difficult to separate the desired polynitrohexaazaisowurtzitane derivative from the by-produced nitroaromatic compounds.
It is also difficult to obtain HCW in high yields. The reason for this is considered to reside in that, during the production of HCW, hydrochloric acid (which is a strong acid) is generated, and the generated hydrochloric acid is likely to decompose HBW as a starting material.
Thus, all of the W skeleton-containing compounds of HBW, TADBW and HCW are not suitable as precursors which can be advantageously used for producing a polynitrohexaazaisowurtzitane derivative, such as HNW or the like, on a commercial scale.
SUMMARY OF THE INVENTION
In these situations, with a view toward developing a commercially advantageous method for producing a polynitrohexaazaisowurtzitane derivative, the present inventors have made extensive and intensive studies in order to find not only a precursor which can be easily converted to a polynitrohexaazaisowurtzitane derivative, but also a method for producing the precursor.
As a result, it has unexpectedly been found that a hexaazaisowurtzitane derivative having a polar group moiety comprised only of an N-acyl group and optionally an N—H group is useful as a precursor of a polynitrohexaazaisowurtzitane derivative. The present inventors have also found a commercially advantageous method for producing the above-mentioned hexaazaisowurtzitane derivative in high yield. It has further been found that a hexaazaisowurtzitane derivative having an N-acyl group, an N-alkyl group and optionally an N—H group can be advantageously used as a polyfunctional crosslinking agent. The present invention has been completed based on these novel findings.
It is an object of the present invention to provide the above-mentioned hexaazaisowurtzitane derivative, and it is another object of the present invention to provide a method for producing the same.
It is a further object of the present invention to provide a novel functional material which contains a highly polar, functional group, such as an N-acyl group and an N—H group, in high concentration.
DETAILED DESCRIPTION OF THE INVENTION
In one aspect of the present invention, there is provided an acyl group-containing hexaazaisowurtzitane derivative represented by the following formula (I):
WA
t
Q
(6−t)
(I)
wherein t represents an integer of from 4 to 6, each A independently represents an acyl group having 1 to 10 carbon atoms, each Q independently represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and W represents a hexavalent hexaazaisowurtzitane residue represented by the following formula (II):
In another aspect of the present invention, there is provided a method for producing the above-mentioned acyl group-containing hexaazaisowurtzitane derivative.
Hereinbelow, explanation is made with respect to an acyl group-containing hexaazaisowurtzitane derivative represented by formula (I-a) below, as a typical example of the compound of formula (I) above.
WA
t
H
(6−t)
(I-a)
wherein t represents an integer of from 4 to 6, A represents an acyl group having 1 to 10 carbon atoms, H represents a hydrogen atom, and W represents a hexavalent hexaazaisowurtzitane residue represented by the following formula (II):
With respect to the acyl group A in the hexaazaisowurtzitane derivative of the present invention, there is no particular limitation as long as it has 1 to 10 carbon atoms. The acyl group may be substituted with a substituent which is stable under reaction cond
Ikeda Masanori
Kodama Tamotsu
Tojo Masahiro
Asahi Kasei Kabushiki Kaisha
Coleman Brenda
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
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