US3041337A - Nitraza-alkylene derivatives of heterocyclic azines - Google Patents

Nitraza-alkylene derivatives of heterocyclic azines Download PDF

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US3041337A
US3041337A US666272A US66627257A US3041337A US 3041337 A US3041337 A US 3041337A US 666272 A US666272 A US 666272A US 66627257 A US66627257 A US 66627257A US 3041337 A US3041337 A US 3041337A
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nitraza
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aza
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formaldehyde
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Milton B Frankel
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Aerojet Rocketdyne Inc
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Aerojet General Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/04—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D251/06—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/38—Halogen atoms or nitro radicals

Definitions

  • This invention relates to new compositions of matter and to their preparation. More particularly, this invention relates to heterocyclic compounds .of the following general formula:
  • the heterocyclic nitro compounds of this invention are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge.
  • An example of such a missile is disclosed in United States PatentNo. 2,470,162, issued May 17, 1949.
  • One way of using the high explosives of this invention in a device such as that disclosed in United States Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed.
  • a charge thus prepared is sulficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure developed from ignition of a propellant charge, and can be caused to explode on operation of an impactor time fuse-mechanism firing a detonating explosive such as lead azide or mercury fulminate.
  • the compounds of the present invention are also useful as pharmaceutical intermediates.
  • nitropiperidines of my invention are prepared by condensing a nitraza amine with 2,2,4,4-tetranitro-1,5- pentanediol in accordance with the general reaction scheme set forth below: i
  • the 1,3-diazines of this invention are prepared by conwherein the A and R are as defined above.
  • the solid was recrystallized from chloroform to produce the product 1,3-bis (3'-uitraza-1 '-buty1) ,5 -dinitrohexahydro- 1,3-diazine which had an M.P. of 120-121 C.
  • the nitraza amines used as starting materials for the preparation of the new compounds of this invention are preferably generated in situ from their corresponding strong mineral acid salts by neutralizing the strong mineral acid salts with inorganic basic salts, such as hydroxides, carbonates, or weak organic acid salts, of alkali or alkaline earth metals.
  • inorganic basic salts such as hydroxides, carbonates, or weak organic acid salts, of alkali or alkaline earth metals.
  • sodium hydroxide as my nitraza amine generating agent but other suitable agents such as, calcium hydroxide, magnesium bicarbonate, lithium carbonate, sodium acetate, etc., can be used for this purpose if desired.
  • Any of the strong mineral acid salts such as nitric acid, hydrochloric acid, etc., salts of the nitraza amines can be utilized in the practice of my invention.
  • Reaction temperature is not critical in the practice of this invention, the only elfect of temperature variation being a corresponding increase or decrease in reaction rate.
  • the strong mineral acid salts of nitraza amines from which the free nitraza amines are generated in the practice of this invention are prepared by reacting a corresponding nitraza isocyanate such as, 3-nitraza-1-buty1 isocyanate, with an aqueous solution of a strong mineral acid such as hydrochloric acid, as more fully disclosed in my copending U.S. patent application Serial No. 666,273, now U.S. Patent 3,000,954, filed concurrently with the present application. p
  • nitraza isccyanates are prepared by reacting nitrazaacid halides, such as, 4 nitrazapentanoyl chloride, with alkali or alkaline earth metal azides, as for example, sodium or magnesium azide, to form the corresponding nitraza azides, and subsequently heating the nitraza azides to effect rearrangement to the desired nitraza isocyanate. Treating the 4-nitrazapentanoyl chloride as described results in the formation of 3-nitraza-1-butyl isoeyanate.
  • This method of preparing nitraza isocyanates is more fully disclosed in my copending US, patent application Serial No. 514,384, filed June 9, 195 5, now U.S. Patent 3,000,920.
  • the 2,2,4,4-tetranitro-1,S-pentanediol used as a starting material for the preparation of the nitropiperidines of the present invention can be prepared by reacting an alkali metal, alkaline earth metal, or ammonium salt of 2,2,4,4- tetranitro butanol with formaldehyde, as more fully disclosed in assignees U.S. patent application Serial No. 371,150, now abandoned, filed July 29, 1953.
  • Salts of 2,2,4,4-tetranitro butanol are prepared by acidifying the corresponding salt of dinitro ethanol, as more fully diselosed in assignees U.S. patent application Serial No. 371,149, now abandoned, filed July 29, 1953.
  • the 2,2,4,4- tetranitro butanol salt is prepared by the method of Duden and Poundorf, described in Ber. 38, 2033.
  • diazines of the present invention are prepared by condensing nitraza amines (such as are employed as starting materials for the preparation of the nitropiperidines disclosed herein) with 2,2-dinitro-1,3-propanediol, as more fully disclosed in my copending U.S. patent application Serial No. 666,275, new U.S. Patent 3,000,955, filed concurrently with the present application.
  • the present invention is not limited to substituted hydrogenated 1,3,5-triazines or mtro-substituted hydrogenated 1,3-diazines in which the As and the Rs represent identical radicals, respectively. It .is within the scope of the invention to employ mixtures of suitable nitraza amines for the preparation of my substituted hydrogenated 1,3,5-triazines or to employ dinitramines prepared from mixtures of nitraza amines for the preparation of my nitro-substituted hydrogenated 1,3-diazines. It is thus obvious that the above two classes of compounds include members in which the radicals represented by the Rs and/or the As are not mutually equivalent.
  • the three Rs in the general formula of my substituted hydrogenated 1,3,5-triazines can be identical or separate alkyl or nitroalkyl radicals; any combination of two of the three types of radicals within the scope of the invention (i.e., hydrogen, alkyl and nitroalkyl radicals); or any combination of all three types of radicals within the scope of the invention.
  • heterocyclic compounds can be prepared in accordance with the procedures taught herein.
  • the nitropiperidines: N(4-nitr-aza-1'-hexyl) 3,3,5,5 tetranitropiperidine and N-(3-aza-3',5',5'-trinitro-1'-hexyl)-3,3,5,5-tetranitropiperidine are obtained when 4-nitraza-1-hexylamine and 3-aza-3,5,5-trinitro-l-hexylamine, respectively, are condensed with 2,2,4,4-tetranitro-1,5-pentanediol;
  • A is a lower alkylene radical; and R is lower alkyl, and
  • N-CH2OHl-N-CH2-l-CHS N02 Cg Ha N02 N02 l JHnGHrN-CHr-'$-CH3 which comprises condensing 2,2,4,9-,9,14,16,16-octanitro, 4,7,1LM-tetra-aZaheptadeCane having the structural formula:
  • N02 whichcomprises condensing S-nitrazabutylamine having the structural formula:

Description

rates o No Drawing. Filed June 13, 1957, Ser. No. 666,272 20 Claims. (Cl. 260-248) This invention relates to new compositions of matter and to their preparation. More particularly, this invention relates to heterocyclic compounds .of the following general formula:
wherein X is (NO C= or A is an alkylene radical; and R is a hydrogen, alkyl, or nitroalkyl radical.
The heterocyclic nitro compounds of this invention are useful as high explosives and can be used in any conventional explosive missile, projectile, rocket, or the like, as the main explosive charge. An example of such a missile is disclosed in United States PatentNo. 2,470,162, issued May 17, 1949. One way of using the high explosives of this invention in a device such as that disclosed in United States Patent No. 2,470,162 is to pack the crystalline explosive in powder form into the warhead of the missile. Alternatively, the crystals can be first pelletized and then packed. A charge thus prepared is sulficiently insensitive to withstand the shock entailed in the ejection of a shell from a gun barrel or from a rocket launching tube under the pressure developed from ignition of a propellant charge, and can be caused to explode on operation of an impactor time fuse-mechanism firing a detonating explosive such as lead azide or mercury fulminate.
The compounds of the present invention are also useful as pharmaceutical intermediates.
The nitropiperidines of my invention are prepared by condensing a nitraza amine with 2,2,4,4-tetranitro-1,5- pentanediol in accordance with the general reaction scheme set forth below: i
3041,33? Patented June 26, 1952 EQQ condensing a nitraza amine with formaldehyde in accordance with the general reaction scheme set forth below:
wherein A and R are as defined above.
The 1,3-diazines of this invention are prepared by conwherein the A and R are as defined above.
To more clearly illustrate my invention, the following examples are presented. It should be understood that these examples merely serve as a means of illustrating the invention and that they are not intended to limit the scope of the invention in any way.
EXAMPLE I Preparation of N-(3-Nitraza-1'-Butyl)-3,3,5,5- Tefranitropiperidine A mixture of 2.84 g. (0.01 mole) of 2,2,4,4-tetranitrol,5-pentanediol, 1.56 g. (0.01'mole) of 3-nitraza-1-buty1 ammonium chloride, and 50 ml. of water was warmed to 45-50 C. to effect solution and then cooled to 25 C., after which a solution of 0.82 g. (0.01 mole) of sodium acetate in 10 ml. of water was added thereto. A creamcolored solid precipitated; the solid was washed with water and dried to yield 2.5 g. (68.2%) of a product having an M.P. of 92-94 C. The Washed and dried solid was recrystallized from ethylene dichloride to produce the product, N (3 nitraza l butyl)-3,3,5,5-tetranitr0- piperidine, which had an M.P. of 9698 C.
Analysis.-Calculated 'for C H N- o z percent C, 26.16; percent H, 3.57; percent N, 26.70. Found: percent C, 26.33; percent H, 3.75; percent N, 26.71.
EXAMPLE 11 Preparation of Hexahydr0-1,3,5-Tris (3'-Nitraza-1- Butyl)-1,3,5-Triwzine A mixture of 15.6 g. (0.1 mole) of 3-nitraza-l-tbutyl ammonium chloride, 8.1 g. (0.1 mole) of 37% formalin, and 25 ml. of water was prepared. A solution of 8.2 g. (0.1 mole) of sodium acetate in 15 ml. of water was added dropwise to the aforesaid solution. After stirring for 30 minutes, a white solid which had precipitated from the solution was collected, washed with water, and dried to yield 5.9 g. (45.0%) of a product having an M.P. of 8890 C. The washed and dried solid was recrystallized from ethyl acetate to produce the product, hexahydro- 1,3,5-tris (3'-nitraza1-hutyl)-1,3,5-triazine, which had an M.P. of 9797.5 C.
Analysis.-Calculated for C12H27N9O5Z percent C,
of 4050 C. for one hour.
spams? EXAMPLE III Preparation 07]- 1,3-bis (3-Nitraza-I'-Butyl)-5,5-Dinitr0- hexahydro-l ,3-Diazine A mixture of 3.68 g. (0.01 mole) of 2,5,9,12-tetraaza- 2,7,7,IZ-tetranitrotridecane, 0.81 g. (0.01 mole) of 37% formalin, and 100 ml. of water was stirred at room temperature for one hour and then stirred at a temperature A tan-colored solid formed which was collected and dried to yield 3.2 g. (84.3%) of a mixture having an M.P. of 110-115 C. The solid was recrystallized from chloroform to produce the product 1,3-bis (3'-uitraza-1 '-buty1) ,5 -dinitrohexahydro- 1,3-diazine which had an M.P. of 120-121 C.
Analysis.Calculated for c H N O t percent C,
31.58; percent H, 5.30; percent N, 29.46. Found: percent C, 31.72; percent H, 5.36; percent N, 28.70.
As a matter of convenience, the nitraza amines used as starting materials for the preparation of the new compounds of this invention are preferably generated in situ from their corresponding strong mineral acid salts by neutralizing the strong mineral acid salts with inorganic basic salts, such as hydroxides, carbonates, or weak organic acid salts, of alkali or alkaline earth metals. For reasons of convenience and economy, I prefer to use sodium hydroxide as my nitraza amine generating agent but other suitable agents such as, calcium hydroxide, magnesium bicarbonate, lithium carbonate, sodium acetate, etc., can be used for this purpose if desired. Any of the strong mineral acid salts such as nitric acid, hydrochloric acid, etc., salts of the nitraza amines can be utilized in the practice of my invention.
Optimum results are obtained in the nitraza amine condensation reactions when the reactions are conducted at a pH below about 8 and preferably within the range from about 4 to about 8.
Reaction temperature is not critical in the practice of this invention, the only elfect of temperature variation being a corresponding increase or decrease in reaction rate.
The strong mineral acid salts of nitraza amines from which the free nitraza amines are generated in the practice of this invention are prepared by reacting a corresponding nitraza isocyanate such as, 3-nitraza-1-buty1 isocyanate, with an aqueous solution of a strong mineral acid such as hydrochloric acid, as more fully disclosed in my copending U.S. patent application Serial No. 666,273, now U.S. Patent 3,000,954, filed concurrently with the present application. p
The nitraza isccyanates are prepared by reacting nitrazaacid halides, such as, 4 nitrazapentanoyl chloride, with alkali or alkaline earth metal azides, as for example, sodium or magnesium azide, to form the corresponding nitraza azides, and subsequently heating the nitraza azides to effect rearrangement to the desired nitraza isocyanate. Treating the 4-nitrazapentanoyl chloride as described results in the formation of 3-nitraza-1-butyl isoeyanate. This method of preparing nitraza isocyanates is more fully disclosed in my copending US, patent application Serial No. 514,384, filed June 9, 195 5, now U.S. Patent 3,000,920.
The 2,2,4,4-tetranitro-1,S-pentanediol used as a starting material for the preparation of the nitropiperidines of the present invention can be prepared by reacting an alkali metal, alkaline earth metal, or ammonium salt of 2,2,4,4- tetranitro butanol with formaldehyde, as more fully disclosed in assignees U.S. patent application Serial No. 371,150, now abandoned, filed July 29, 1953. Salts of 2,2,4,4-tetranitro butanol are prepared by acidifying the corresponding salt of dinitro ethanol, as more fully diselosed in assignees U.S. patent application Serial No. 371,149, now abandoned, filed July 29, 1953. The 2,2,4,4- tetranitro butanol salt is prepared by the method of Duden and Poundorf, described in Ber. 38, 2033.
The dinitrarnines suitable as starting materials for the preparation of the nine-substituted hydrogenated 1,3-
diazines of the present invention are prepared by condensing nitraza amines (such as are employed as starting materials for the preparation of the nitropiperidines disclosed herein) with 2,2-dinitro-1,3-propanediol, as more fully disclosed in my copending U.S. patent application Serial No. 666,275, new U.S. Patent 3,000,955, filed concurrently with the present application.
It should be pointed out that the present inventionis not limited to substituted hydrogenated 1,3,5-triazines or mtro-substituted hydrogenated 1,3-diazines in which the As and the Rs represent identical radicals, respectively. It .is within the scope of the invention to employ mixtures of suitable nitraza amines for the preparation of my substituted hydrogenated 1,3,5-triazines or to employ dinitramines prepared from mixtures of nitraza amines for the preparation of my nitro-substituted hydrogenated 1,3-diazines. It is thus obvious that the above two classes of compounds include members in which the radicals represented by the Rs and/or the As are not mutually equivalent. For example, the three Rs in the general formula of my substituted hydrogenated 1,3,5-triazines can be identical or separate alkyl or nitroalkyl radicals; any combination of two of the three types of radicals within the scope of the invention (i.e., hydrogen, alkyl and nitroalkyl radicals); or any combination of all three types of radicals within the scope of the invention.
It will be appreciated that a wide variety of heterocyclic compounds can be prepared in accordance with the procedures taught herein. For example, the nitropiperidines: N(4-nitr-aza-1'-hexyl) 3,3,5,5 tetranitropiperidine and N-(3-aza-3',5',5'-trinitro-1'-hexyl)-3,3,5,5-tetranitropiperidine are obtained when 4-nitraza-1-hexylamine and 3-aza-3,5,5-trinitro-l-hexylamine, respectively, are condensed with 2,2,4,4-tetranitro-1,5-pentanediol; the substituted hydrogenated 1,3,5-triazines: hexahydro-1,3,5- tris (4-nitraza-1-hexyl)-1,3,5-triazine and hexahydro- 1,3,5-tris (3'-aza-3',5',5'-trinitro-1'-hexyl) 1,3,5 triazine are obtained when 4-nitraza-1-hexylamine and 3-aza- 3,5,5-trinitro-l-hexylamine, respectively, are condensed with formaldehyde; and the nitro-sub stituted hydrogenated 1,3-diazines: 1,3-bis (4'*nitraza-1'-hexyl)-5,5-dinitrohexahydro-1,3-diazine and 1,3-bis (3'-aza-3',5',5-trinitro-1'- hexyl)-5,5-dinitrohexahydro-1,3-diazine are obtained when 3,7,11,15 tetraaza 3,9,9,l5 tetranitroheptadecane and 2,2,4,9,9,14,16,16 octanitro 4,7,11,14 tetraazaheptacleeane, respectively, are condensed with formaldehyde. Other heterocyclic compounds within the scope of my invention can be prepared simply by reacting appropriate starting materials as taught herein.
I claim:
1. As a new composition of matter, pound having the general formula:
1 r CH1 CH1 a heterocyclic com- N01 wherein X is a radical selected from the group consisting of (N0 C: and
a radical selected A is a lower alkylene radical; and R is lower alkyl, and
o Ngdni /(5ENO2 l CHzCHzCHz-IYL-CHaCHa 4. As a new composition of matter, N-(3-aza-3',5',5'- trinitrohexyl)-3,3,5,5-tetranitropiperidine having the structural formula:
5. As a new composition of matter, hexahydro-1,3,5- tris (S-nitrazabutyl)-1,3,5-triazine having the structural 6. As a new composition of matter, hex-ahydro-l,3,5- tris (4-nitrazahexy1)-1,3-5-triazine having the structural OH; NO:
7. As a new composition of matter, heXahydro-1,3,5- tris (3-aza-3,5f,5'-trinitrohexyl)-1,3,5-triazine having the structural formula:
8. As a new composition of matter, 1,3-bis (3-nitrazabutyl)-5,5-dinitrohexahydro-1,B-diazine having the structural formula:
NO\2 /Cg2 N02 N CHgCHr-NCH 02 C 2 C 2 CH2CH2-IITOH3 hexyl)-5,5-dinitrohexahydro-1,3-diazine having the structural formula:
6 10. As a newvcomposition of matter, 1,3-bis (3'-aza- 3',5',5'-trinitrohexyl)-5,5-dinitrohexahydro 1,3 diazine having the structural formula:
No, CH N02 No,
\C/ NCH2CHrI ICHr-(B-CH3 b16611, $11, so, \N/ N01 ('JHzCHr-N-CHr-l-CHa 11. The method of preparing heterocyclic compounds having the general formula:
CH2 a (7H1 43H:
( 1Hl-A-N-GHlR which comprises condensing a compound selected from the group consisting of nitraza amines having the general formula R'CH2-I1T'A-CH2NH2 and dinitramines having the general formula:
with a compound selected from the group consisting of 2,2,4,4 tetranitro 1,5 pentanediol and formaldehyde; wherein X is a radical selected from the group consisting of (NO C= and N02 =NCH2AI ICHz-R A is a lower alkylene radical; and R is a radical selected from the group consisting of hydrogen, lower alkyl, and lower nitroalkyl radicals.
12. The method of preparing N-(3'-nitrazabuty l)- 3,3,5,5-tetranitropiperidine having the structural formula:
No: 0E2 N02 NfiHa ENOfl CHflCH2 CHg I N02 which comprises condensing 3-nitrazabutylamine having the structural formula:
I: CH3-N-C H2 0 H2-N Hg with 2,2,4,4-tetranitro1,S-pentanediol.
13. The method of preparing N-(4'-nitrazahexy1)-3,3,
5,5-tetranitropipe1'idine having the structural formula:
which comprises condensing 4-nitrazahexylamine having the structural formula:
IP02 CHaCHa-N-CHzCHaCHr-NH: with 2,2,4,4-tetranitro-l,S-pentanediol.
14. The method of preparing N-(3'-aza-3,S',5-trinitrohexyl)-3,3,5,5-tetranitropiperidine having the structural formula:
which comprises condensing 3-aza-3,5,5-trinitrohexylamine having the structural formula:
with formaldehyde.
16. 'The method of preparing 1,3bis (4-nitrazahexyl)- 5,5-dinitrohexahydro-1,3-diazine having the structural formula:
HnCHaCHr-IL-CHECH:
which comprises condensing 3,7,11,15-tetraaza-3,9,9',15- tetranitroheptadecane having the structural formula:
N 11 N0, 11 N0, CH3cfirlk -cHnCHQGHz-llT-CHr-(J-CH2NQHzCHaCH:-lI-CH:CH;
with formaldehyde.
17. The method of preparing 1,3-bis (3'-aza-3,5',5'- trinitrohexyl)-5,5-dinitrohexahydro-1,3-diazine having the structural formula:
No, or n 1 10, No,
N-CH2OHl-N-CH2-l-CHS N02 Cg: Ha N02 N02 l JHnGHrN-CHr-'$-CH3 which comprises condensing 2,2,4,9-,9,14,16,16-octanitro, 4,7,1LM-tetra-aZaheptadeCane having the structural formula:
with formaldehyde.
18. The method of preparing hexahydro-1,3,5-tris (3'- nitrazahutyl)1,3,5-triazine having the structural formula:
N02 whichcomprises condensing S-nitrazabutylamine having the structural formula:
1Y0: OHs-NCHzCHz-NH with formaldehyde.
19. The method of preparing hexahydro-1,3,5-tris (4'- nitrazahexyl)1,3,5-triazine having the structural formula:
which comprises condensing 4-nitrazahexylamine having the structural formula:
lilOa omonr-m-oI-nommm-NH,
with formaldehyde.
20. The method of preparing hexahydro-1,3,5-tris (3- -aza-3,5',5'-trinitrohexyl)-1,3,5-triazine having the struc tural formula:
which comprises condensing 3 aza3,5,5-trinitrohexylamine having the structural formula:
with formaldehyde.
References Cited in the file of this patent Walter: Formaldehyde, 2nd ed., pages 281 to 284, Reinhold Publishing Corp. (1953).
Smolin et =a1.: s-Triazines and Derivatives, page 563, Interscience Publishers, Inc., New York (February 1959).

Claims (2)

1. AS A NEW COMPOSITION OF MATTER, A HETEROCYCLIC COMPOUND HAVING THE GENERAL FORMULA:
11. THE METHOD OF PREPARING HETEROCYCLIC COMPOUNDS HAVING THE GENERAL FORMULA:
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3915970A (en) * 1972-03-24 1975-10-28 Coalite Chem Prod Ltd Hexahydro-1,3,5-triazines
US3940298A (en) * 1974-12-06 1976-02-24 The United States Of America As Represented By The Secretary Of The Navy Thermal laser pumped with high nitrogen content propellants
US4346222A (en) * 1980-12-04 1982-08-24 Sri International 1,3,5,5-Tetranitrohexahydropyrimidine (DNNC)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3915970A (en) * 1972-03-24 1975-10-28 Coalite Chem Prod Ltd Hexahydro-1,3,5-triazines
US3940298A (en) * 1974-12-06 1976-02-24 The United States Of America As Represented By The Secretary Of The Navy Thermal laser pumped with high nitrogen content propellants
US4346222A (en) * 1980-12-04 1982-08-24 Sri International 1,3,5,5-Tetranitrohexahydropyrimidine (DNNC)

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