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US2929699A - Explosive - Google Patents

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Publication number
US2929699A
US2929699A US550294A US55029444A US2929699A US 2929699 A US2929699 A US 2929699A US 550294 A US550294 A US 550294A US 55029444 A US55029444 A US 55029444A US 2929699 A US2929699 A US 2929699A
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Prior art keywords
explosive
triaminoguanidine
explosives
salts
acid
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US550294A
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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
    • C06B25/04Compositions containing a nitrated organic compound the nitrated compound being an aromatic
    • 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

Definitions

  • the present invention relates to-an explosive compopurposes without the We have discovered that certain salts of triaminoguanidine are explosives possessing highly favorable characteristics which make them of value for military and commercial applications. These explosive compounds are represented by the type formula:
  • triaminoguanidine perchlorate which is not only a powerful high explosive, crushing 51 g. 'of sand in the sand test as compared with 22 g. for the same weight of mercuric fulminate, but like the latter maybe initiated to detonation by the spit of a black powder fuze. It is furthermore extremely sensitive 1' to impact and will detonate when subjected to the blow The complete conversion of the ammonia of a 2 kg. hammer when dropped from a height of only 7 cm.
  • triaminoguanidine compounds can be shown by calculation to yield relatively low temperature on explo- Patlented Mar. 22, 1960 and picrate of triaminoguanigiven in the above table with sion and would therefore offer advantages over many other high explosives where a cool explosive isdesired.
  • An explosive composition consisting essentiall'yof tiaminoguanidine salt of an acidic agent selectedfrom the group consisting of nitric acid; picric acid; 'perchloric 15 acid; chloric acid, hydrazoic acid; styphnic acid; ,dinitrophenol; and dinitroresorcinol, and a detonating'agent'for said salt.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

sition.
- organic acids which will (see structural Formulas I and II).
t have beenreplaced by the dine cannot be so detonated when derivative of The invention described hereinmay be manufactured and-.used by or for the Government for governmental payment to us of any royalty thereon.
The present invention relates to-an explosive compopurposes without the We have discovered that certain salts of triaminoguanidine are explosives possessing highly favorable characteristics which make them of value for military and commercial applications. These explosive compounds are represented by the type formula:
' NH-Nmi whereHX represents any one of a series of inorganic or the triaminoguanidinewhen combined with it. t
Triaminoguanidine is structurally related to carbonic acid and may in fact be looked upon as the hydrazine analog of carbonic acid in which the oxygen and hydroxyl groupshave been replaced by groupings, =N-NH and HNH respectively In a similar manner triaminoguanidine is related structurally to guanidine (see structural Formula HI) except that in this instance the amino, NH and imino, =NH, groups of guanidine corresponding isosteric hydrajzme groupings.
I v II III Carbonic acid Trlaminoguanidine Guanidine on NH-NH; NH, g c o O=NNH, C\=\NH on NHNH= NH:
Whilev the acid derivatives of guanidine have been have found that they do, not possess the favorable proper- ,ties of the correspondingtriaminoguanidine salt" and have not been used for military or industrial purposes so far as is known due largely to the extreme insensitivity of the compounds. We have discovered that the sensitivity of the triaminoguanidine salts as well as of diaminoguanidine salts, covered by our copending application, is such that they canbe readily broughtjto complete high order detonation by a priming charge of-mer- 'curic fulminate, whereas the corresponding salts of guanitested under the same conditions.
carbonic acid, i.e., of guanidine into the corresponding hydrazine derivative triaminoguanidine has a marked effect in increasing the sensitivity of the salts, that is, the ease in which the salts can be made to explode. This is considered an important discovery as no reference to such an effect has yet been encountered in the field of explosives. It is of particular interest that these new more sensitive explosive salts of triaminoguanidine can be used, per se, as high explosives.
part explosives properties to the isosteric hydrazine a United States Pater-re In :fact, one off these, triaminoguanidine perchlorate is 3 actually capable of beinginitiated to detonation by the previously considered for use in explosive mixtures, we
order and at a high rate with v. of storage and use to which spit of a blackpowderfuze.
-,IIot only do the triaminoguanidine salts possess favor alile sensitivity, to, initiation, but they have been found to be stable towards storage at temperatures far above thoseusually met withundercondition s of use, and they have been foundtoexhibitpower andbrisance comparable to trinitrotoluene and other high explosives'which have found extensive use as 'ftaryexplosives.
Themore important; and significant explosive characs; teristics of typical inorganic and organic salts of triamino standard methods are sum 'guanidine, -,as determined by marized in Table I. While we cite here, for purposes of illustration only the nitrate dine, we do not wish to be limited to these salts, for it is indicated that such acids as chloric, hydrazoic, styphnic, dinitrophenol, dinitroresorcinol andthe like will combine with the base to give exposive products.
Comparison of the values those for well known explosives will serve to emphasize their favorable properties. Both triaminoguanidine salts are safer to handle in bulk than the important military explosive, pentaerythritol tetranitrate which explodes when subjected to the drop of 2 kg. weight of only 17 cm. 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. Since these sandtest values were obtained under standard test conditions through initiation by 0.3 g. of mercuric fulminate, it is furthermore pertinent from a practical point of view that these explosives can easily be made to detonate at high commonly used initial detonating agents. The figures for stability indicate that triaminoguanidine compounds possess excellent stability and would undergo no decomposition under the conditions military and commercial explosives are now subjected. They are, in fact, more stable than such widely used high explosive compositions as 35/65 trinitrotoluene/trinitrophenylmethylnitramine and 50/50 trinitrotoluene/pentaerythritol. tetranitrate both of which fail in this same test.
Particular reference is made to triaminoguanidine perchlorate Which is not only a powerful high explosive, crushing 51 g. 'of sand in the sand test as compared with 22 g. for the same weight of mercuric fulminate, but like the latter maybe initiated to detonation by the spit of a black powder fuze. It is furthermore extremely sensitive 1' to impact and will detonate when subjected to the blow The complete conversion of the ammonia of a 2 kg. hammer when dropped from a height of only 7 cm. These characteristics place the perchlorate of triaminoguanidine in the same class with other powerful initiating agents, such as mercury fulminate and lead azide, but it differs from these by virtue of the fact that it possesses an extraordinarily high brisance or shattering efiect. Its use as an initiator or as a component of priming and detonating compositions is thereby indicated.
The triaminoguanidine compounds can be shown by calculation to yield relatively low temperature on explo- Patlented Mar. 22, 1960 and picrate of triaminoguanigiven in the above table with sion and would therefore offer advantages over many other high explosives where a cool explosive isdesired. Triaminoguanidine compounds, in particular thenitrate,
can also be used as componentsfof mixed explosives.
We-have found (a) that an explosive mixtureconsisting" of a 50/50 mixture of triaminoguanidinenitrate plus trinitrotoluene possesses greater brisance than, the widely used composite of ammonium nitrate and trinit'rot'oluene'j and (b)' thatsuch a mixture in the moltenstate can be? cast loaded into shell, bombs, mines; and other devices used for blasting and demolition purposes,
We claim:
An explosive composition consisting essentiall'yof tiaminoguanidine salt of an acidic agent selectedfrom the group consisting of nitric acid; picric acid; 'perchloric 15 acid; chloric acid, hydrazoic acid; styphnic acid; ,dinitrophenol; and dinitroresorcinol, and a detonating'agent'for said salt.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Beilstein: Handbuchider Organi cfl Chemie, vol. 1 (1st sup. tothe4thed.),p a 57 I I I Davis: ry of Powder and Explosives," II,
pages 280-81 (1943).
US550294A 1944-08-19 1944-08-19 Explosive Expired - Lifetime US2929699A (en)

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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3226438A (en) * 1960-02-01 1965-12-28 Dow Chemical Co Method for the preparation of triaminoguanidine
US3293853A (en) * 1962-07-02 1966-12-27 Monsanto Res Corp Eutectics of triaminoguanidine perchlorate with lithium perchlorate and propulsive method
US3322042A (en) * 1965-02-16 1967-05-30 Economy Tooling Company Box breaker
US3375230A (en) * 1962-01-24 1968-03-26 Dow Chemical Co High nitrogen polymers prepared by reacting aldehydes with aminoguanidines, tetrazoles, or triazoles
US3909323A (en) * 1973-06-14 1975-09-30 Rockwell International Corp Cool burning gun propellants containing triaminoguanidine nitrate and cyclotetramethylene tetranitramine with ethyl cellulose binder
US3950196A (en) * 1973-06-14 1976-04-13 Rockwell International Corporation Cool-burning gun propellant containing triaminoquanidine ethylene dinitramine
US3954528A (en) * 1970-11-06 1976-05-04 The United States Of America As Represented By The Secretary Of The Navy Solid gas generating and gun propellant composition containing triaminoguanidine nitrate and synthetic polymer binder
US4047987A (en) * 1973-02-27 1977-09-13 Director-General Of The Agency Of Industrial Science And Technology Underwater blasting explosives
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
US4381958A (en) * 1980-08-07 1983-05-03 Hercules Incorporated Triaminoguanidine nitrate-containing propellants
US4472214A (en) * 1982-06-18 1984-09-18 Rockwell International Corporation Triaminoguanidinium phosphate propellant additive
US5024708A (en) * 1988-02-10 1991-06-18 Contec Chemieanlagen Gmbh Castable and/or pressable gas generating propellants
US20100116385A1 (en) * 2005-03-30 2010-05-13 Alliant Techsystems Inc. Methods of forming a sensitized explosive and a percussion primer
US20110100246A1 (en) * 2006-03-02 2011-05-05 Alliant Techsystems Inc. Percussion primers comprising a primer composition and ordnance including the same
US8206522B2 (en) 2010-03-31 2012-06-26 Alliant Techsystems Inc. Non-toxic, heavy-metal free sensitized explosive percussion primers and methods of preparing the same
US8454769B2 (en) 2007-02-09 2013-06-04 Alliant Techsystems Inc. Non-toxic percussion primers and methods of preparing the same
US8454770B1 (en) 2007-02-09 2013-06-04 Alliant Techsystems Inc. Non-toxic percussion primers and methods of preparing the same
US8540828B2 (en) 2008-08-19 2013-09-24 Alliant Techsystems Inc. Nontoxic, noncorrosive phosphorus-based primer compositions and an ordnance element including the same
US8641842B2 (en) 2011-08-31 2014-02-04 Alliant Techsystems Inc. Propellant compositions including stabilized red phosphorus, a method of forming same, and an ordnance element including the same

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 (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3226438A (en) * 1960-02-01 1965-12-28 Dow Chemical Co Method for the preparation of triaminoguanidine
US3375230A (en) * 1962-01-24 1968-03-26 Dow Chemical Co High nitrogen polymers prepared by reacting aldehydes with aminoguanidines, tetrazoles, or triazoles
US3293853A (en) * 1962-07-02 1966-12-27 Monsanto Res Corp Eutectics of triaminoguanidine perchlorate with lithium perchlorate and propulsive method
US3322042A (en) * 1965-02-16 1967-05-30 Economy Tooling Company Box breaker
US3954528A (en) * 1970-11-06 1976-05-04 The United States Of America As Represented By The Secretary Of The Navy Solid gas generating and gun propellant composition containing triaminoguanidine nitrate and synthetic polymer binder
US4047987A (en) * 1973-02-27 1977-09-13 Director-General Of The Agency Of Industrial Science And Technology Underwater blasting explosives
US3909323A (en) * 1973-06-14 1975-09-30 Rockwell International Corp Cool burning gun propellants containing triaminoguanidine nitrate and cyclotetramethylene tetranitramine with ethyl cellulose binder
US3950196A (en) * 1973-06-14 1976-04-13 Rockwell International Corporation Cool-burning gun propellant containing triaminoquanidine ethylene dinitramine
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
US4381958A (en) * 1980-08-07 1983-05-03 Hercules Incorporated Triaminoguanidine nitrate-containing propellants
US4472214A (en) * 1982-06-18 1984-09-18 Rockwell International Corporation Triaminoguanidinium phosphate propellant additive
US5024708A (en) * 1988-02-10 1991-06-18 Contec Chemieanlagen Gmbh Castable and/or pressable gas generating propellants
US20100116385A1 (en) * 2005-03-30 2010-05-13 Alliant Techsystems Inc. Methods of forming a sensitized explosive and a percussion primer
US8282751B2 (en) 2005-03-30 2012-10-09 Alliant Techsystems Inc. Methods of forming a sensitized explosive and a percussion primer
US8460486B1 (en) 2005-03-30 2013-06-11 Alliant Techsystems Inc. Percussion primer composition and systems incorporating same
US20110100246A1 (en) * 2006-03-02 2011-05-05 Alliant Techsystems Inc. Percussion primers comprising a primer composition and ordnance including the same
US8524018B2 (en) 2006-03-02 2013-09-03 Alliant Techsystems Inc. Percussion primers comprising a primer composition and ordnance including the same
US9199887B2 (en) 2006-03-02 2015-12-01 Orbital Atk, Inc. Propellant compositions including stabilized red phosphorus and methods of forming same
US8454769B2 (en) 2007-02-09 2013-06-04 Alliant Techsystems Inc. Non-toxic percussion primers and methods of preparing the same
US8454770B1 (en) 2007-02-09 2013-06-04 Alliant Techsystems Inc. Non-toxic percussion primers and methods of preparing the same
US8540828B2 (en) 2008-08-19 2013-09-24 Alliant Techsystems Inc. Nontoxic, noncorrosive phosphorus-based primer compositions and an ordnance element including the same
US8206522B2 (en) 2010-03-31 2012-06-26 Alliant Techsystems Inc. Non-toxic, heavy-metal free sensitized explosive percussion primers and methods of preparing the same
US8470107B2 (en) 2010-03-31 2013-06-25 Alliant Techsystems Inc. Non-toxic, heavy-metal free explosive percussion primers and methods of preparing the same
US8641842B2 (en) 2011-08-31 2014-02-04 Alliant Techsystems Inc. Propellant compositions including stabilized red phosphorus, a method of forming same, and an ordnance element including the same

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