EP0210881B1 - Verwendung von 5-Oxo-3-nitro-1,2,4-triazol als Sekundär-Sprengstoff und 5-Oxo-3-nitro-1,2,4-triazol enthaltende pyrotechnische Zusammensetzungen - Google Patents

Verwendung von 5-Oxo-3-nitro-1,2,4-triazol als Sekundär-Sprengstoff und 5-Oxo-3-nitro-1,2,4-triazol enthaltende pyrotechnische Zusammensetzungen Download PDF

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Publication number
EP0210881B1
EP0210881B1 EP86401282A EP86401282A EP0210881B1 EP 0210881 B1 EP0210881 B1 EP 0210881B1 EP 86401282 A EP86401282 A EP 86401282A EP 86401282 A EP86401282 A EP 86401282A EP 0210881 B1 EP0210881 B1 EP 0210881B1
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EP
European Patent Office
Prior art keywords
composition according
binder
explosive
triazole
oxo
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Expired
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EP86401282A
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English (en)
French (fr)
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EP0210881A1 (de
Inventor
Alain Becuwe
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Societe Nationale des Poudres et Explosifs
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Societe Nationale des Poudres et Explosifs
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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B43/00—Compositions characterised by explosive or thermic constituents not provided for in groups C06B25/00 - C06B41/00
    • 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
    • C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine

Definitions

  • the present invention relates to a new secondary explosive and to new pyrotechnic compositions, in particular new explosive compositions.
  • Secondary explosives and pyrotechnic compositions such as explosive compositions, powders for weapons, propellants are very commonly used both in the arms industries and in the civil field: space technology, mining and quarrying, public works , etc.
  • the secondary explosives satisfying these two conditions used to date are mainly cyclotetramethylene tetranitramine, also called octogen or HMX, cyclotrimethylene trinitramine, also called hexogen or RDX.
  • the sensitivity of explosives depends, among other things, on the commercial variety. With regard to hexogen, the results are given for two of them (B and CH).
  • Impact sensitivity and friction sensitivity are determined using Julius Peters apparatus, according to the method described by HDMALLORY (The development of impact sensitivity tests at the Explosive Research Laboratory, Bruceton, PENNSYLVANIA during the years 1941 - 1945 US Naval Ordnance Lab .; White Oak, MARYLAND, 1956, report 4236).
  • octogen and hexogen have the major advantage of having a density and a detonation rate that are significantly higher.
  • these compounds have the disadvantage of being very much more sensitive to impact and friction than tolite, hence certain difficulties or constraints of use.
  • a binder either plastic and inert, or active, such as molten tolite, has been incorporated into the compositions.
  • active such as molten tolite
  • TATB and tolite have a low sensitivity to external aggressions (shock, friction, temperature rise) which makes it possible to reduce the vulnerability of the compositions, at the cost, however, of a drop in performance.
  • 5-oxo 3-nitro 1,2,4-triazole (commonly called oxynitrotriazole) has interesting properties which make it possible to use it as a secondary explosive in place of the octogen or hexogen, while having a sensitivity as low as that of tolite.
  • Oxynitrotriazole has the enormous advantage of having explosive performances close to those of hexogen, given its high density without having the sensitivity of hexogen or octogen (see Table 1).
  • substitution of all or part of the hexogen by oxynitrotriazole makes it possible to reduce the vulnerability of the explosive compositions while maintaining practically the same level of performance.
  • substitution of part of the octogen by oxynitrotriazole makes it possible, while maintaining a satisfactory level of performance, to reduce the vulnerability of the explosive compositions in order to meet a need of users, a need which loading with octogen alone does not not allow to answer.
  • oxynitrotriazole can be used as an oxidizing charge in place of the explosive substances commonly used in gun powders such as triple base powders and composite powders as well as in composite propellants.
  • oxynitrotriazole to replace ammonium nitrate in composite gas-generating propellants has several advantages, the most important of which is the fact that oxynitrotriazole is significantly less hygroscopic than ammonium nitrate.
  • the present invention therefore relates to the use of 5-oxo 3-nitro 1,2,4-triazole as a secondary explosive. It also aims to provide new pyrotechnic compositions, and in particular new explosive compositions, characterized in that they contain 5-oxo 3-nitro 1,2,4-triazole. Among these new pyrotechnic compositions one can also mention new powders for weapons and new propellants.
  • 5-oxo 3-nitro 1,2,4-triazole compound of formula FIG00 / 40 commonly called oxynitrotriazole, is also sometimes called oxonitrotriazole or nitrotriazolone.
  • Oxynitrotriazole is for example obtained in 2 stages from two common raw materials: semicarbazide hydrochloride and formic acid.
  • the second step consists in nitrating the oxytriazole thus obtained, for example with 98% nitric acid, at ambient temperature, for a few hours.
  • Oxynitrotriazole is isolated from the medium according to a conventional technique well known to those skilled in the art, with an overall yield, for all of the 2 stages, close to 65%.
  • Oxynitrotriazole has a detonation speed close to that of hexogen and the sensitivities on impact and friction are very much lower than those of octogen and hexogen, the sensitivities obtained for oxynitrotriazole being close to those obtained for tolite.
  • Crystallization tests in particular in water with slow stirring (regular, almost spherical crystals with an average diameter of about 100 to 150 ⁇ m) and in water with stirring but with programmed cooling to 0 ° C, have shown the possibility of obtaining crystals large enough to be easily used in formulations.
  • oxynitrotriazole in addition to its use as a secondary explosive in the form of a pure product, oxynitrotriazole can be used in pyrotechnic compositions and in particular explosive compositions.
  • It can also be used as a secondary explosive in mixture with a compound in which it is practically insoluble and allowing loading in the molten state (use with molten tolite for example).
  • Oxynitrotriazole can also be used as a secondary explosive in mixture with waxes or more generally with plastics allowing loading by compression.
  • Oxynitrotriazole can also be used as an oxidizing charge in powders for weapons, in particular triple base powders and composite powders as well as in composite propellants.
  • the new explosive compositions according to the invention are characterized in that they contain 5-oxo 3-nitro 1,2,4-triazole. They are obtained according to conventional methods and well known to those skilled in the art by substituting all or part of the secondary explosives usually used by oxynitrotriazole.
  • the explosive compositions are explosive compositions with a plastic binder used by compression. Such compositions are produced according to conventional methods well known to those skilled in the art for obtaining explosive plastic binder compositions used by compression. We can for example cite those described in French patents 1 602 614 and 1 469 198.
  • the basic material consists of granules in which the crystals of explosives are coated with a plastic material.
  • thermoplastic binders for example polyester binders
  • the explosive compositions according to this first preferred variant of the invention one can distinguish those containing no other secondary explosive than 5-oxo 3-nitro 1,2,4-triazole and those which, on the contrary, contain at least another secondary explosive than 5-oxo 3-nitro 1,2,4-triazole such as for example HMX, RDX, TATB, HNS or PETN.
  • those containing at least one secondary explosive chosen from the group formed by octogen and hexogen are preferred.
  • the plastic binder is chosen from the group consisting of fluorinated binders, polyurethane binders and polyester binders.
  • the other binders usually used in explosive compositions with plastic binder used by compression are also suitable. Mention may for example be made of binders based on butadiene-styrene copolymers.
  • the explosive compositions are explosive compositions with a plastic binder used by casting.
  • Such compositions are produced according to conventional methods well known to those skilled in the art for obtaining explosive compositions used by casting. These include, for example, those described in French patents 2,124,038, 2,225,979 and 2,086,881.
  • the secondary explosive (s) and a liquid polymerizable resin are firstly mixed and then the paste obtained is poured into a mold. The dough is then polymerized.
  • the crosslinking agents catalysts, wetting agents, explosive molded compositions of various characteristics are obtained.
  • the explosive compositions according to this second preferred variant one can distinguish those containing no other secondary explosive than 5-oxo 3-nitro 1,2,4-triazole and those which, on the contrary, contain at least one other explosive secondary than 5-oxo 3-nitro 1,2,4-triazole, preferably chosen from the group formed by octogen and hexogen.
  • the weight content of the binder in the explosive composition being between 12 and 20%.
  • the other binders usually used in explosive compositions with plastic binder used by casting are also suitable. Mention may for example be made of silicone binders and polyester binders, in particular those obtained by reaction of an epoxide with a carboxy-telechelic polybutadiene (PBCT).
  • PBCT carboxy-telechelic polybutadiene
  • the explosive compositions are mixtures based on tolite. These mixtures, used by casting, are produced according to the conventional methods for obtaining mixtures based on tolite currently known as hexolites, pentolites or octolites by replacing all or part of the secondary explosive usually associated with tolite (to namely hexogen, pentrite or octogen) by oxynitrotriazole.
  • mixtures consist of suspensions of grains of oxynitrotriazole in molten tolite. They can, for example, be obtained by direct mixing of oxynitrotriazole in molten tolite. Preferably, the weight content of oxynitrotriazole in these mixtures is between 50 and 90%.
  • the new gun powders according to the invention are characterized in that they contain 5-oxo 3-nitro 1,2,4-triazole. They are obtained according to conventional processes and well known to those skilled in the art by substituting all or part of the secondary explosives usually used as an oxidizing charge in powders with 5-oxo 3-nitro 1,2,4-triazole.
  • the powders for weapons are triple base powders of which the 3 bases are nitrocellulose, nitroglycerin and oxynitrotriazole.
  • the nitrocellulose and nitroglycerin contents are those usually present in the triple base powders containing them, such as for example in the nitrocellulose-nitroglycerin-nitroguanidine triple base powders, the oxynitrotriazole contents being close to those usually present in nitroguanidine.
  • triple base powders may contain the additives conventionally used, namely in particular stabilizers (2-nitrodiphenylamine for example), plasticizers, and antiluents.
  • the powders for weapons are composite powders with an inert binder. They are mainly constituted by a synthetic resin and by one or more explosive substances playing the role of oxidizing charge.
  • oxidizing charges which can be associated with oxynitrotriazole in powder for weapons according to this second preferred variant
  • the inert binder is preferably a polyurethane binder but it can also for example and without limitation be a polyester binder.
  • polyurethane binders those obtained by reacting a hydroxylated polybutadiene with a diisocyanate are preferred.
  • the level of binder is of the order of 20% by weight.
  • the composite powders according to the invention also generally contain the usual additives known to those skilled in the art, such as in particular plasticizers, anti-oxidant, anti-glow, anti-erosive agents.
  • the powders with an inert binder for weapons according to the invention can be obtained according to the conventional methods for obtaining this type of powder, and in particular by the "global” technique which is very widely used and which has already been previously described for the production. explosive compositions with plastic binder used by casting.
  • the new composite propellants according to the invention are characterized in that they contain 5-oxo 3-nitro 1,2,4-triazole. They are obtained according to conventional methods and well known to those skilled in the art by substituting all or part of the explosive substances usually used as an oxidizing charge in propellants with 5-oxo 3-nitro 1,2,4-triazole. They can be obtained according to the conventional methods for obtaining composite propellants and in particular by the "global” technique called “casting" which is very widely used and which has already been described previously.
  • binder-filler adhesion agents antioxidants, catalysts.
  • the composite propellants according to the invention are gas-generating propellants in which the oxynitrotriazole substitutes all or part of the ammonium nitrate usually used in these compositions.
  • such composite gas-generating propellants consisting of those consisting of a polyurethane binder loaded with oxynitrotriazole.
  • the weight content in binder is of the order of 20% and that in oxynitrotriazole of the order of 80%.
  • the composite propellants according to the invention contain at least one other secondary explosive than oxynitrotriazole chosen from the group consisting of hexogen and octogen, the binder preferably being a polyurethane binder.
  • the content by weight of binder is for example of the order of 20% and that of the total charges of about 80%.
  • oxytriazole 170 g of oxytriazole are introduced into 750 ml of 98% nitric acid while maintaining the temperature at 5-10 ° C. The addition lasts 2 hours. Then stirred for 3 hours at room temperature. This nitric bath is then slowly poured into 600 ml of ice water and left to stand for a dozen hours. After filtration, spinning and drying, 208 g of oxynitrotriazole are obtained, which is in the form of a white solid identified by its IR, NMR and mass spectra. The overall yield of all 2 stages is 64%.
  • the detonation speed of such an oxynitrotriazole cord is 7,400 m / s.
  • the detonation speed of this cord is 7,770 m / s.
  • This composition consists of 7% by weight of the fluorinated binder sold under the trade name "Kel F 800" by the company 3M and 93% by weight of fillers.
  • the charges are oxynitrotriazole and octogen in the relative proportions by weight 50/50.
  • the binder is introduced in solution in ethyl acetate in a mixer with the solid fillers. After mixing under reduced pressure, which makes it possible to remove the solvent, the granules thus obtained are dried under vacuum and then compressed at 110 ° C. under a pressure of 1.5108 Pa.
  • the explosive characteristics of this composition are grouped in Table 2, compared with those of 2 known compositions containing 7% by weight of the same binder Kelf 800 and 93% by weight of fillers; for one of them, these charges are TATB and octogen in the relative proportions by weight 60/40 respectively and for the other octogen only. It can be seen that the composition with oxynitrotriazole is less sensitive to shock and friction than that with TATB while the detonation speed is higher and that the initiation by detonation wave remains entirely satisfactory.
  • Example 5 the same composition is made as in Example 4, but the filler consists only of oxynitrotriazole.
  • the binder is a polyurethane binder, sold under the trade name ESTANE by the company GOODRICH.
  • the binder is a polyamide (nylon) binder.
  • the binder is a polyvinyl acetate binder, sold under the trade name RHODO HV2 by the company RHONE-POULENC.
  • compositions of Examples 5 to 11 contain as fillers a mixture of octogen and oxynitrotriazole; they were carried out according to the same method as that of Example 4.
  • Example 5 The explosive characteristics of the composition of Example 5 are grouped in Table 3 compared with those of 2 known compositions, one charged with octogen, the other with TATB.
  • compositions with oxynitrotriazole on the one hand and with TATB on the other hand are very little sensitive to shock, friction and shock wave compared to that of octogen.
  • compositions consist of 19.4% by weight of a polyurethane binder obtained by reaction of the hydroxylated polyester sold under the trade name T1271 by the company ISEL with isophorore diisocyanate (IPDI) and 80.6% by weight of fillers. .
  • the fillers are oxynitrotriazole and octogen in the relative proportions by weight 44/56 respectively for Example 12 and 58/42 respectively for Example 13.
  • successively are introduced, with intermediate kneading under pressure reduced, hydroxylated polyester, fillers and isocyanate.
  • the paste obtained is poured into molds and then polymerized by baking at 40 ° C for 8 days.
  • the explosive characteristics of these compositions are grouped in Table 5, compared with those of 2 known compositions containing 19.4% by weight of the same binder and 80.6% by weight of fillers. For one of them, the charges are TATB and octogen in the relative proportions by weight 44/56 respectively and for the other octogen only.
  • the mechanical properties of the compositions are similar.
  • the detonation speed of the compositions containing on the one hand the TATB and on the other hand the oxynitrotriazole are close to and slightly lower than that of the composition solely charged with octogen.
  • shock wave sensitivity is lowered by the substitution of part of the octogen by TATB or by oxynitrotriazole. Unexpectedly, however, the drop is significantly greater with oxynitrotriazole than with TATB.
  • the initiability (sensitivity to the BRISKA detonator, possibly with plastic relay) is lowered by the substitution of part of the octogen by TATB or by oxynitrotriazole.
  • the solvent couple used is acetone-ethanol in the 50/50 mass ratio and the watering rate is 70% compared to dry nitrocellulose.
  • the triple base monotubular powder obtained does not show any particular sensitivity. It presents a Friction sensitivity of 309 N, ignition by an electrical spark greater than 726 mJ and ignition by capacitive discharges in a confined environment greater than 15.6 J.
  • Firing in a 200 cm 3 gauge bomb at several loading densities (0.12; 0.15; 0.18; 0.20 and 0.23 g / cm3) made it possible to determine the combustion speed curve. It is very regular. There is a speed of 110 mm / s at 100 MPa.
  • the flame temperature is low (3600 K) compared to that of a double base nitrocellulose nitroglycerine 60/40 powder (about 3900 K) while the density is close. It is, however, superior to that of a triple base powder with nitroguanidine (around 3000 K).
  • the theoretical strength (1.15 MJ / kg) is on the other hand greater than that of a triple base powder with nitroguanidine (1.08 MJ / kg) but slightly less than that of a double base (1.19 MJ / kg).
  • the powder produced is in the form of cylindrical grains having 7 channels parallel to the axis of the grains. It is used for large caliber ammunition.
  • composition by weight is as follows:
  • the mixture of the various ingredients of the composition except for the isocyanate, is firstly homogenized in a kneader, at 60 ° C. under reduced pressure. Part of the isocyanate is then added so that the NCO / OH ratio is 0.72. After homogenization, the dough is pre-crosslinked at 60 ° C for 5 days, then it is introduced into an extruder mixer. The remainder of the isocyanate is then added and the paste is extruded through a die having the desired final geometry of the powder.
  • the strands obtained are then heated at 60 ° C for 2 days, then cut into grains.
  • Manometric bombs were used to measure a combustion speed of 40 mm / s at 100 MPa and a force of 0.97 MJ / kg.
  • the flame temperature is 2211 K.
  • the powder containing the oxynitrotriazole according to the invention has a lower flame temperature. (2211 K instead of 2430 K) and a lower concentration of reducing gases such as H 2 and CO.
  • a gas generator composite propellant consisting of 81% by weight of oxynitrotriazole and 19% by weight of a polyurethane binder was produced.
  • the basic components of this binder are hydroxylated polybutadiene R45M and methylenedicyclohexyldiisocyanate.
  • This binder also contains a plasticizer (dioctyl azelate), an antioxidant (ionol) and lecithin.
  • This composite propellant was produced according to the conventional so-called "global” or “casting” method using an NCO / OH ratio of 1.

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Claims (21)

1. Verwendung des 5-Oxo-3-nitro-1,2,4-triazols als Sekundärsprengstoff.
2. Pyrotechnische Zusammensetzung, gekennzeichnet durch den Gehalt an 5-Oxo-3-nitro-1,2,4-triazol.
3. Pyrotechnische Zusammensetzung nach Anspruch 2 in Form eines Sprengstoffs.
4. Pyrotechnische Zusammensetzung nach Anspruch 3 in Form eines Sprengstoffs mit einem Kunststoff-Bindemittel, der durch Pressen verarbeitet wurde.
5. Pyrotechnische Zusammensetzung nach Anspruch 3 in Form eines Verbund-Sprengstoffs mit einem Kunststoff-Bindemittel, der durch Gießen verarbeitet wurde.
6. Pyrotechnische Zusammensetzung nach einem der Ansprüche 3 bis 5, dadurch gekennzeichnet, daß sie keinen anderen Sekundärsprengstoff als 5-Oxo-3-nitro-1,2,4-triazol enthält.
7. Pyrotechnische Zusammensetzung nach einem der Ansprüche 3 bis 5, dadurch gekennzeichnet, das sie mindestens einen anderen Sekundärsprengstoff als 5-Oxo-3-nitro-1,2,4-triazol enthält.
8. Pyrotechnische Zusammensetzung nach Anspruch 4 oder 5, dadurch gekennzeichnet, daß sie mindestens einen anderen Sekundärsprengstoff, wie Octogen oder Hexogen, enthält.
9. Pyrotechnische Zusammensetzung nach Anspruch 4, dadurch gekennzeichnet, daß das Kunststoff-Bindemittel unter fluorierten Bindemitteln, Polyurethan- oder Polyester-Bindemitteln ausgewählt ist.
10. Pyrotechnische Zusammensetzung nach Anspruch 5, dadurch gekennzeichnet, das das Bindemittel ein Polyurethan in einer Menge von 12 bis 20 Masse-%, bezogen auf den Sprengstoff, ist.
11. Pyrotechnische Zusammensetzung nach Anspruch 3 auf der Basis von Trinitrotoluol, die ausgehend von geschmolzenem Trinitrotoluol verarbeitet wurde.
12. Pyrotechnische Zusammensetzung nach Anspruch 11, gekennzeichnet durch einen Gehalt an 5-Oxo-3-nitro-1,2,4-triazol von 50 bis 90 Masse-%.
13. Pyrotechnische Zusammensetzung nach Anspruch 2 als Schießpulver.
14. Pyrotechnische Zusammensetzung nach Anspruch 13 in Form eines Pulvers auf Dreifachbasis, wobei die drei Basen Nitrozellulose, Nitroglycerin und 5-Oxo-3-nitro-1,2,4-triazol sind.
15. Pyrotechnische Zusammensetzung nach Anspruch 13 in Form eines Verbundpulvers mit inertem Bindemittel.
16. Pyrotechnische Zusammensetzung nach Anspruch 15, gekennzeichnet durch mindestens einen anderen Sekundärsprengstoff, gewählt unter Hexogen, Octogen und Pentrit.
17. Pyrotechnische Zusammensetzung nach Anspruch 15 oder 16, gekennzeichnet durch ein Polyurethan als inertes Bindemittel.
18. Pyrotechnische Zusammensetzung nach einem der Ansprüche 15 bis 17, gekennzeichnet durch einen Gehalt an Bindemittel in der Größenordnung von 20 %.
19. Pyrotechnische Zusammensetzung nach Anspruch 2 als Verbundpropergol.
20. Pyrotechnische Zusammensetzung nach Anspruch 19, gekennzeichnet durch einen Gehalt an etwa 20 Masse-% eines Polyurethan-Bindemittels und etwa 80 Masse-% 5-Oxo-3-nitro-1,2,4-triazol.
21. Pyrotechnische Zusammensetzung nach Anspruch 19, gekennzeichnet durch ein Polyurethan-Bindemittel und mindestens einem anderen Sekundärsprengstoff als 5-Oxo-3-nitro-1,2,4-triazol, gewählt unter Hexogen und Octogen.
EP86401282A 1985-06-28 1986-06-13 Verwendung von 5-Oxo-3-nitro-1,2,4-triazol als Sekundär-Sprengstoff und 5-Oxo-3-nitro-1,2,4-triazol enthaltende pyrotechnische Zusammensetzungen Expired EP0210881B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8509885 1985-06-28
FR8509885A FR2584066B1 (fr) 1985-06-28 1985-06-28 Utilisation du 5-oxo 3-nitro, 1,2,4-triazole comme substance explosive et compositions pyrotechniques contenant du 5-oxo 3-nitro 1,2,4-triazole.

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EP0210881A1 EP0210881A1 (de) 1987-02-04
EP0210881B1 true EP0210881B1 (de) 1989-10-25

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US (1) US5034072A (de)
EP (1) EP0210881B1 (de)
JP (1) JPH0829997B2 (de)
CA (1) CA1304228C (de)
DE (1) DE3666582D1 (de)
FR (1) FR2584066B1 (de)

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US5034072A (en) 1991-07-23
JPS623088A (ja) 1987-01-09
EP0210881A1 (de) 1987-02-04
FR2584066A1 (fr) 1987-01-02
CA1304228C (en) 1992-06-30
DE3666582D1 (en) 1989-11-30
JPH0829997B2 (ja) 1996-03-27
FR2584066B1 (fr) 1987-08-07

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