US2929698A - Explosive - Google Patents

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US2929698A
US2929698A US549599A US54959944A US2929698A US 2929698 A US2929698 A US 2929698A US 549599 A US549599 A US 549599A US 54959944 A US54959944 A US 54959944A US 2929698 A US2929698 A US 2929698A
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explosives
explosive
diaminoguanidine
salts
compounds
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US549599A
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Ludwig F Audrieth
George C Hale
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    • CCHEMISTRY; METALLURGY
    • C06EXPLOSIVES; MATCHES
    • C06BEXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00Compositions containing a nitrated organic compound
    • C06B25/34Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
    • CCHEMISTRY; METALLURGY
    • C06EXPLOSIVES; MATCHES
    • C06BEXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00Compositions containing a nitrated organic compound
    • C06B25/04Compositions containing a nitrated organic compound the nitrated compound being an aromatic

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  • the present invention relates to a new explosive composition. More particularly the invention is based upon the discovery that certain salts of diaminoguanidine are explosives having highly favorable properties which make them of value for military or other uses. Such explosive compounds are represented by the type formula:
  • HX represents any one of a series of inorganic or organic acids which will impart explosive properties to diaminoguanidine when combined with it.
  • the impactsensitivity of tetryl and of pentaerythritol tetranitrate is given by the values 17 cm. and 26 cm. respectively, indicating that both the nitrate and picrate of diaminoguanidine are appreciably less sensitive to impact and therefore much safer to handle than these widely used high explosives.
  • the sand test values generally recognized by those skilled in the art as a measure of the brisance or shattering effect of an explosive, place these compounds in the same class with trinitrotoluene and the amatols.
  • diaminoguanidine compounds can be shown by calculation to yield relatively low temperature on explosion, and would therefore offer advantage over many other high explosives where a cool explosive is desired.
  • Diaminoguanidine compounds, in particular the nitrate can also be used as components of mixed explosives. We have found (a) that an explosive consisting of a 50/50 mixture of diaminoguanidine nitrate plus trinitrotoluene possesses greater power and brisance than the widely used composite of ammonium nitrate and trinitrotoluene;

Description

- onated when tested under the 2,929,698 f EXPLOSIVE Ludwig F. Audrieth and George C. Hale, Dover, NJ.
No Drawing. Application August 15, 1944 Serial No. 549,599
7 1 Claim. 01. 52-5 (Granted under Title'35, us. Code 1952 sec. 266) The invention described herein may be manufactured and used by or for the Government for governmental purposes without the payment to us of any royalty thereon.
The present invention relates to a new explosive composition. More particularly the invention is based upon the discovery that certain salts of diaminoguanidine are explosives having highly favorable properties which make them of value for military or other uses. Such explosive compounds are represented by the type formula:
where HX represents any one of a series of inorganic or organic acids which will impart explosive properties to diaminoguanidine when combined with it.
While it is recognized that the acid derivatives of guanidine have been considered previously for use in explosives mixtures, we have found that they do not possess the favorable properties of the diaminoguanidine salts and, in fact, have not been used as military or industrial explosives so far as is known, due largely to the extreme insensivity to the compounds. We have discovered that the sensitivity of the diaminoguanadine salts is such that they can be readily brought to complete high order detonation by a priming charge of mercury fulminate, Whereas the corresponding salts of guanidine cannot be so detsame conditions. Evidently, the replacement of two amino groups in guanidine by hydrazine groups to produce diaminoguanidine (see structural formulas I and II) has a marked elfect in increasing the sensitivity of the salts, i.e., the ease in which the salts can be made to explode.
This is considered an important discovery as no reference to such an efiect has yet been encountered in the field of explosives. It is of definite interest that these new, more explosive salts of diaminoguanidine can be used alone as high explosives.
In addition to the favorable sensitivity to detonation of the diaminoguanidine salts, they have been found to be highly stable and to have power or brisance comparable to trinitrotoluene and to other explosives which have found extensive use as military explosives. H
The more important and significant explosive characteristics of representative inorganic and organicsalts of diaminoguanidine, as determined standard methodaare summarized iolloyyi i'e table? A Dmmmoguanzdme Nitrate Plcrate Melting Point. 0 142-4 188-90 Sensitivity to irnpact, Bureau of Mines App. using a 2 kg. wt;., cm 40 80 Sand Test value. g. sand when initiated with 0.3 g.
mercuric fulminate 27. 8 40. 6 Stability, cc. gas evolved by a 5 g. sample in the 120 Vacuum Stability Test 1.92 0.48 Explosion Temperature, 0 290 250 While we cite here only the nitrate and picrate of diaminoguanidine, we do not wish to be limited to these two salts, for we have found that such acids as perchloric, chloric, hydrazoic, styphnic, dinitrophenol, and dinitroresorcinol will combine with the base to give explosive products.
' To emphasize the favorable properties of these compounds as explosives, the following comparisons are made.
The impactsensitivity of tetryl and of pentaerythritol tetranitrate is given by the values 17 cm. and 26 cm. respectively, indicating that both the nitrate and picrate of diaminoguanidine are appreciably less sensitive to impact and therefore much safer to handle than these widely used high explosives. The sand test values, generally recognized by those skilled in the art as a measure of the brisance or shattering effect of an explosive, place these compounds in the same class with trinitrotoluene and the amatols.
Since the sand test values for the nitrate and picrate of diamino-guanidine areobtained through initiation by'0.3 g. of mercuric fulminate, it is furthermore indicated that these explosives can easily be made to detonate at high order and at a high rate. Particularly favorable and of utmost importance in determining the feasibility of using for military and commercial purposes such explosives is the stability of diaminoguanidine compounds. In fact the data indicates that the compounds cited above as examples are remarkably stable in that heating for 48 hours, in a vacuum at 120 C. causes only negligible decomposition as evidenced by the small quantity of gas evolved in the .test. By comparison, these compounds possess stability approaching that of trinitrotoluene and are more stable than tetryl and pentaerythritol tetranitrate, all of which are important military high explosives.
The diaminoguanidine compounds can be shown by calculation to yield relatively low temperature on explosion, and would therefore offer advantage over many other high explosives where a cool explosive is desired. Diaminoguanidine compounds, in particular the nitrate, can also be used as components of mixed explosives. We have found (a) that an explosive consisting of a 50/50 mixture of diaminoguanidine nitrate plus trinitrotoluene possesses greater power and brisance than the widely used composite of ammonium nitrate and trinitrotoluene;
and (b) that such a mixture in the molten state can be cast loaded into shell, bombs, mines, and other devices used for blasting and demolition purposes to yield an excellent high explosive of high power and superior phenol and dinitroresorcinol, and a detonating agent for detonating said salt.
(References on following page) 4 OTHER REFERENCES Davis: Chemistry of Powder and Explosives, 11, pages 280-81 (1943).
References Cited iii the file of this patent UNITED STATES PATENTS 1,312,464 Woodbury Aug. 5, 1919 1,758,169 Olsen. May 13, 1930 5 Beilstem: Handbuch der Orgamsche Chemie, vol.
7 VI (4th ed.), page 279.
FOREIGN PATENTS Beilstein: Handbuch der Organische Chemie, vol.
12,617 Great Britain 1901 III (1st sup. to the 4th edition), page 57.
US549599A 1944-08-15 1944-08-15 Explosive Expired - Lifetime US2929698A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3247035A (en) * 1962-09-28 1966-04-19 Standard Oil Co Ammonium nitrate propellants containing a nitro-aminocarboxy-alkali metal phenolate combustion catalyst
US3375230A (en) * 1962-01-24 1968-03-26 Dow Chemical Co High nitrogen polymers prepared by reacting aldehydes with aminoguanidines, tetrazoles, or triazoles
US4094710A (en) * 1973-08-16 1978-06-13 The United States Of America As Represented By The Secretary Of The Navy Explosive composition containing guanidinium picrate
US6045638A (en) * 1998-10-09 2000-04-04 Atlantic Research Corporation Monopropellant and propellant compositions including mono and polyaminoguanidine dinitrate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB190112617A (en) * 1901-02-08 1901-10-12 Alvaro Alberto Da Silva New or Improved Explosives.
US1312464A (en) * 1919-08-05 Cotofty
US1758169A (en) * 1925-10-16 1930-05-13 Olsen Fredrich Explosive composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1312464A (en) * 1919-08-05 Cotofty
GB190112617A (en) * 1901-02-08 1901-10-12 Alvaro Alberto Da Silva New or Improved Explosives.
US1758169A (en) * 1925-10-16 1930-05-13 Olsen Fredrich Explosive composition

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3375230A (en) * 1962-01-24 1968-03-26 Dow Chemical Co High nitrogen polymers prepared by reacting aldehydes with aminoguanidines, tetrazoles, or triazoles
US3247035A (en) * 1962-09-28 1966-04-19 Standard Oil Co Ammonium nitrate propellants containing a nitro-aminocarboxy-alkali metal phenolate combustion catalyst
US4094710A (en) * 1973-08-16 1978-06-13 The United States Of America As Represented By The Secretary Of The Navy Explosive composition containing guanidinium picrate
US6045638A (en) * 1998-10-09 2000-04-04 Atlantic Research Corporation Monopropellant and propellant compositions including mono and polyaminoguanidine dinitrate

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