EP3071537B1 - Pyrotechnisches zusammengesetztes produkt mit unvernetztem bindemittel und verfahren zur herstellung davon - Google Patents

Pyrotechnisches zusammengesetztes produkt mit unvernetztem bindemittel und verfahren zur herstellung davon Download PDF

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Publication number
EP3071537B1
EP3071537B1 EP14809915.3A EP14809915A EP3071537B1 EP 3071537 B1 EP3071537 B1 EP 3071537B1 EP 14809915 A EP14809915 A EP 14809915A EP 3071537 B1 EP3071537 B1 EP 3071537B1
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EP
European Patent Office
Prior art keywords
charges
energetic
plasticizer
gum
composite pyrotechnic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP14809915.3A
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English (en)
French (fr)
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EP3071537A1 (de
Inventor
Nancy Desgardin
Philippe Ragon
Mathieu W. Werschine
Caroline CARAYON
Jean-Louis Paulin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eurenco SA
ArianeGroup SAS
Original Assignee
Eurenco SA
Eurenco France SA
Herakles SA
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Application filed by Eurenco SA, Eurenco France SA, Herakles SA filed Critical Eurenco SA
Priority to PL14809915T priority Critical patent/PL3071537T3/pl
Publication of EP3071537A1 publication Critical patent/EP3071537A1/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B21/00—Apparatus or methods for working-up explosives, e.g. forming, cutting, drying
    • C06B21/0008—Compounding the ingredient
    • C06B21/0025—Compounding the ingredient the ingredient being a polymer bonded explosive or thermic component

Definitions

  • the present invention relates to composite pyrotechnic products, particularly suitable as propellant powders for tube weapons (more particularly for tank artillery). These are composite pyrotechnic products, which contain a high level of energetic charges in a binder. These products are particularly interesting, especially in terms of strength (of energy power), vulnerability (see below a reminder on this concept, familiar to the skilled person), and scope of application as to the nature of loads that they can contain. They can opportunely be optimized in terms of erosivity.
  • the present invention also relates to a process for preparing said composite pyrotechnic products. Said method is of a particularly easy implementation.
  • Known propellant powders consisting of one or more gelatinized energy bases having a homogeneous appearance (hence their name).
  • homogeneous propellant powders mention may be made of "smoke-free" powders based on nitrocellulose alone or based on a nitrocellulose-nitroglycerine mixture.
  • organic (powdery) energy charges These charged powders no longer have a homogeneous appearance, but a heterogeneous appearance in which we distinguish on the one hand, the energy binder and on the other hand, the charges.
  • Such charged powders are called “composite” or “heterogeneous”. Such charged powders are for example described in the French patent application FR 2,488,246 .
  • Vulnerability is defined as the property that powders can be able to ignite and deflag under the effect of a physical, random, undesired phenomenon, such as the impact of a projectile. Vulnerability is a major defect for powders intended to be loaded on board battle tanks. The development of modern combat gear has therefore led the skilled person to look for propellant powders that are not very vulnerable.
  • inert binder composite powders consisting mainly of organic energy charges in a synthetic resin.
  • Such powders are much less vulnerable than homogeneous powders or composites with energy binders (nitrocellulose).
  • energy binders nitrocellulose.
  • these powders must, in order to deliver the necessary energy during firing, contain very high levels of charges, often close to 80% of the total mass of the powder.
  • the inert binder composite powders thus have the characteristic of containing very little binder with respect to their powdery filler.
  • the precursor mixtures of these powders must, however, be able to be worked (in particular being able to be calendered or spun through a die of relatively small diameter, most often including pins intended to create the channels present in the final strand of powder), and the powders must keep their geometric shape in time. It is particularly with reference to obtaining these composite propellant powders with inert binder for tube weapons that the skilled person has encountered and still faces serious difficulties.
  • thermoplastic binders of synthetic origin, that can be used in the preparation of composite pyrotechnic products and present in their composition, exist to date as thermoplastic binders and as thermosetting binders (obtained from oligomers).
  • thermoplastic binders allow, in theory, temperature, a mechanical work of the product to give it the desired geometry. It should, however, of course, that the working temperature (to which the binder is deformable) is compatible with the stability of the present charges and, with reference to this unavoidable requirement, it is often necessary to involve a solvent. The intervention of such a solvent increases the implementation of the process.
  • EP 0 036 481 discloses a method of manufacturing composite explosives with thermoplastic binder.
  • the patent application IN 498 / DEL / 2001 discloses a method of preparing propellant containing hexogen (RDX) fillers in a thermoplastic binder.
  • RDX hexogen
  • thermosetting binders obtained from oligomers
  • polyurethane binders crosslinkable
  • the dosages of the crosslinking agent (diisocyanate) for carrying out the pre-crosslinking are delicate. They require great precision.
  • the field of application of said technique is limited, in view of the nature of the intervening crosslinking agent (of isocyanate type, to react with hydroxyl functions), as to the nature of the energy charges present, in the as some energy charges (having intrinsic acidity) are likely to react, in a parasitic reaction, with said crosslinking agent (isocyanate type) present.
  • the presence of such fillers (EDNA, nitropyrazoles, for example) is therefore problematic for managing the steps of pre-crosslinking and complementary crosslinking.
  • composite pyrotechnic products particularly suitable as propellant powders for tube weapons, of a new type.
  • These (new) composite pyrotechnic products contain a high level of filler in a binder of a new type (this binder is neither a thermoplastic binder nor a thermoset binder).
  • composite pyrotechnic products are particularly interesting in terms of strength (they contain a high rate of energy charges), of vulnerability (they do not contain nitrocellulose and can advantageously contain energy charges that are not very vulnerable), of a process for obtaining (Their process of obtaining is of a particularly easy implementation (it does not include in particular step of crosslinking and therefore does not involve the use of agent (s) crosslinking)) and they can also be Optimized in terms of erosivity (they can advantageously contain EDNA loads as a total or partial substitution of RDX loads).
  • the composite pyrotechnic products of the invention therefore contain a high level of organic energy charges in a binder of a new type: a binder, gum type ("raw rubber"), uncrosslinked. It is seen further that said binder is likely to contain a plasticizer.
  • the composite pyrotechnic products of the invention therefore contain a high level of organic energy charges: from 78 to 90% by weight, advantageously from 80 to 86% by weight.
  • organic charges of any type (not selected, as in the context of thermally crosslinkable binders, taking into account the crosslinking reaction to be carried out subsequently), the mineral fillers having been discarded insofar as they generate solid particles) are not per se original.
  • organic energy charges known per se and, for the most part, already packaged according to the prior art in a conventional organic polymeric binder (such as PBHT), in particular crosslinked.
  • RDX hexogen
  • HMX octogen
  • NGU nitroguanidine
  • EDNA ethylene dinitramine
  • GUDN dinitramide N-guanylurea
  • 1,1-diamino-2,2-dinitroethylene FOX 7 (DADE)
  • TAGZT triaminoguanidinium
  • DHDZT dihydrazinium 5,5'-azotetrazolate
  • HBT bis (2,2-dinitropropyl) nitramine
  • BDNPN 2,2-dinitropropyl) nitramine
  • organic energetic charges of EDNA particularly preferably, there is a mixture of EDNA charges and RDX charges. It is by no means excluded to find only RDX loads or EDNA loads, but as noted above, mixes of EDNA loads and RDX loads can achieve an optimum in reference to the strength tradeoff. / erosivity. It is understood that the more these mixtures contain RDX, the more they are energetic but the more they are erosive.
  • the energy charges are in the form of solid grains, distributed homogeneously within the binder. These solid grains suitably have, in a known manner per se, several particle size distributions.
  • the organic energy charges are therefore within an original binder.
  • Said original binder is based on an eraser of the type specified. According to a variant, it consists essentially of said gum (at least one additive being present in a small amount), or it consists of said gum. According to another variant, it consists essentially of said gum and at least one plasticizer (at least one additive being present in a small amount), or it consists of said gum and at least one plasticizer.
  • Such a rubber is perfectly suitable for the purposes of the invention, insofar as, in the proportions indicated (only 10 to 22%, it is recalled that high load products are involved), 1) it allows to work mechanically mixing (charges + gum) at low temperature, ie at a temperature below 120 ° C, or even below 100 ° C (fully compatible with the stability of the present charges), and without the use of solvent; and 2) it gives the final product the mechanical and cohesive strength required.
  • Said gum generally consists of a polyurethane-polyester gum or a polyurethane-polyether, but mixtures of at least two gums (at least two polyurethane-polyester gums, at least two polyurethane-polyether gums or at least one polyurethane-polyester gum and at least one polyurethane-polyether gum, such gum mixtures (gums within the meaning of the invention) constituting a gum within the meaning of the invention) having the required properties (mentioned above) may be used.
  • Said gum advantageously consists of a polyurethane-polyester gum.
  • composition of the composite pyrotechnic products of the invention is therefore likely to contain at least one plasticizer.
  • at least one plasticizer (energetic or non-energetic), present, is generally at a level of 2 to 8% by weight (of the total composition).
  • Such at least one plasticizer advantageously consists, with reference to the strength of the product, in at least one energetic plasticizer.
  • composition of the composite pyrotechnic products of the invention therefore advantageously contains at least one energetic plasticizer (an energetic plasticizer, at least two energetic plasticizers, or at least one energetic plasticizer and at least one non-energetic plasticizer), very advantageously it contains a plasticizer energy.
  • the energy plasticizer (s) in question is (are) advantageously of the nitrate and / or nitramine type.
  • the energy plasticizer (s) in question is (are) very advantageously chosen from diethylene glycol dinitrate. (DEGDN), triethylene glycol dinitrate (TEGDN), butanetriol trinitrate (BTTN), trimethylolethane trinitrate (TMETN), a mixture of 2,4-dinitro-2,4-diaza-pentane, 2,4 -dinitro-2,4-diaza-hexane and 3,5-dinitro-3,5-diaza-heptane (and especially DNDA 5.7), nitrato ethyl nitramines (especially methyl-2-nitratoethyl nitramine ( methylNENA) and ethyl-2-nitratoethyl nitramine (ethylINENA)) and mixtures thereof.
  • DEGDN diethylene glycol dinitrate.
  • TAGDN triethylene glycol dinitrate
  • BTTN butanetriol trinitrate
  • processing agent candellila wax and / or paraffin, for example
  • the composite pyrotechnic products of the invention are perfectly suitable as propellant powder for tube weapons. Said composite pyrotechnic products of the invention therefore advantageously consist of such powders.
  • the composite pyrotechnic products of the invention, as described above, are also suitable, in particular, as tactical propellant, explosive composition and gas generator.
  • a pasty mixture is thus produced, the precursor of the final product aimed at.
  • a pasty mixture is advantageously made by twin-screw (extrusion) or twin-cylinder, depending on the quantities to be used. It is usually done at a temperature between 60 ° C and 120 ° C (end values included). It is often carried out at a temperature of 80 ° C. It is understood that this mixing temperature is a function of the nature of the gum and the presence or absence of at least one plasticizer.
  • the product is prepared in the desired form (n products are generally prepared). Said third step is therefore analyzed as a step of shaping the dough.
  • This formatting can include spinning or calendering.
  • the spun product is generally cut into strands (to the desired length).
  • Such strands suitable as propellant powders for tube weapons, generally have a length of 2 to 20 mm, for a diameter of 1 to 20 mm (more generally for a diameter of 2 to 15 mm).
  • the calendered product in the form of a plate (such a plate generally has a thickness of 10 to 20 mm), is generally cut into platelets.
  • EDNA ethylene dinitramine
  • the medium was stirred for 30 minutes at room temperature.
  • the mixture was poured on a bath of cold water at about 5 ° C. with stirring.
  • the solid was then separated from the mother liquors by filtration, and washed several times with distilled water to neutral pH and then filtered off. It was then taken up, wet, for the synthesis of EDNA.
  • the decarboxylation step was carried out by adding DNEU to an aqueous solution buffered with hot sodium acetate. Gaseous evolution (of CO 2 ) was observed, which requires a fractional introduction of the powder.
  • the reaction medium was then cooled so that the EDNA precipitated.
  • the suspension was then filtered and dried. A yield of 85% was obtained.
  • Trioxyethylene glycol dinitrate (TEGDN) was obtained by nitration in a sulfonitrile medium of trioxyethylene glycol.
  • Composite pyrotechnic products of the invention of three types were prepared and tested. Their mass composition and their force (measured or calculated) are respectively given in Tables 1, 2 and 3 below. Below each of said tables 1, 2 and 3 are specified other characteristics of said products.
  • Step b of the process of the invention the pasty mixtures were obtained by twin-cylinder, in a known manner per se.
  • the gum was first introduced between the rolls of the bi-roll (rolling mill), brought to a temperature of 65 ° C. It has been softened. Then, a mixture + plasticizer charges (previously made in a container) was added. To the resulting mixture was then added candelilla wax.
  • Step c of the process of the invention the pasty mixtures obtained were introduced into a press pot heated to 80 ° C to effect spinning at a pressure of between 280 and 320 bar. After cutting, we obtained strands of powder (diameter: 10 mm, length: 11 mm).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (15)

  1. Pyrotechnisches zusammengesetztes Produkt, dessen Zusammensetzung, ausgedrückt in Gewichtsprozent, enthält:
    - 78 bis 90 %, vorteilhafterweise 80 bis 86 % organische energetische Füllstoffe und
    - 10 bis 22 % eines Polymergummis, ausgewählt aus Polyester-Polyurethan-Gummis, Polyether-Polyurethan-Gummis und Mischungen davon, deren zahlenmittlere Molekularmasse größer als 20.000 g/mol ist und deren Mooney-Viskosität zwischen 20 und 70 ml (5 + 4) bei 100 °C beträgt.
  2. Pyrotechnisches zusammengesetztes Produkt gemäß Anspruch 1, dadurch gekennzeichnet, dass die organischen energetischen Füllstoffe aus Füllstoffen aus Hexogen, Octogen, Nitroguanidin, Ethylendinitramin, N-Guanylharnstoff-Dinitramid, 1,1-Diamino-2,2Dinitroethylen, Bis(-triaminoguanidinium)-5,5'-azotetrazolat, Dihydrazinium-5,5'-azotetrazolat, 5,5'-bis(Tetrazolyl)hydrazin, Bis(2,2-dinitropropyl)nitramin, einem Nitropyrazol oder einer Mischung solcher Füllstoffe bestehen.
  3. Pyrotechnisches zusammengesetztes Produkt gemäß Anspruch 1 oder 2, dadurch gekennzeichnet, dass die organischen energetischen Füllstoffe Füllstoffe aus Ethylendinitramin, vorteilhafterweise Füllstoffe aus Hexogen und Füllstoffe aus Ethylendinitramin enthalten.
  4. Pyrotechnisches zusammengesetztes Produkt gemäß einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das Polymergummi eine zahlenmittlere Molekularmassevon über 50.000 g/mol, insbesondere von über 75.000 g/mol aufweist.
  5. Pyrotechnisches zusammengesetztes Produkt gemäß einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass das Gummi ein Polyester-Polyurethan-Gummi oder ein Polyether-Polyurethan-Gummi, vorteilhafterweise ein Polyester-Polyurethan-Gummi ist.
  6. Pyrotechnisches zusammengesetztes Produkt gemäß einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass seine Zusammensetzung ferner mindestens einen energetischen oder nicht energetischen, vorteilhafterweise einen energetischen Weichmacher enthält, wobei der Weichmacher 2 bis 8 % des Gewichts der Zusammensetzung des pyrotechnischen Produkts darstellt.
  7. Pyrotechnisches zusammengesetztes Produkt gemäß Anspruch 6, dadurch gekennzeichnet, dass der mindestens eine Weichmacher ein energetischer Weichmacher vom Typ des Nitrats und/oder Nitramins ist.
  8. Pyrotechnisches zusammengesetztes Produkt gemäß Anspruch 7, dadurch gekennzeichnet, dass der mindestens eine Weichmacher ausgewählt ist aus Diethylenglykoldinitrat, Triethylenglykoldinitrat, Butantrioltrinitrat, Trimethyloläthan, einer Mischung aus 2,4-Dinitro-2,4-diaza-pentan, 2,4-Dinitro-2,4-diaza-hexan und 3,5-Dinitro-3,5-diaza-heptan, Nitratoethylnitramine und Mischungen davon.
  9. Pyrotechnisches zusammengesetztes Produkt gemäß einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass seine Zusammensetzung ferner 0,1 bis 2 Massenprozent von mindestens einem Zusatzstoff enthält, der insbesondere aus den Umsetzungsstoffen und den Stabilisatoren ausgewählt ist.
  10. Pyrotechnisches zusammengesetztes Produkt gemäß einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass es aus einem Treibladungspulver für Rohrwaffen besteht.
  11. Verfahren zur Herstellung eines pyrotechnischen zusammengesetzten Produktes gemäß einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, dass es Folgendes aufweist:
    a) das Bereitstellen der nachstehenden Bestandteile:
    - organische energetische Füllstoffe,
    - ein Polymergummi, ausgewählt aus Polyester-Polyurethan-Gummis, Polyether-Polyurethan-Gummis und Mischungen davon, deren zahlenmittlere Molekularmasse größer als 20.000 g/mol ist und deren Mooney-Viskosität zwischen 20 und 70 ml (5 + 4) bei 100 °C beträgt;
    b) das Mischen von diesen in den richtigen Proportionen mit Bezug auf die gewünschte Zusammensetzung des Endproduktes zum Erhalten von einer pastösen Mischung;
    c) das Erhalten aus dieser pastösen Mischung des mindestens einen pyrotechnischen zusammengesetzten Produktes in der gewünschten Form.
  12. Verfahren gemäß Anspruch 11, dadurch gekennzeichnet, dass es ferner das Bereitstellen von mindestens einem energetischen oder nicht energetischen, vorteilhafterweise einem energetischen Weichmacher und/oder von einem Zusatzstoff und das Mischen der Zusatzstoffe und des Gummis mit dem mindestens einen Weichmacher und/oder dem mindestens einen Zusatzstoff zum Erhalten der pastösen Mischung aufweist.
  13. Verfahren gemäß Anspruch 11 oder 12, dadurch gekennzeichnet, dass das Mischen in der Doppelschnecke oder dem Doppelzylinder durchgeführt wird.
  14. Verfahren gemäß einem der Ansprüche 11 bis 13, dadurch gekennzeichnet, dass das Mischen bei einer Temperatur zwischen 60 und 120 °C durchgeführt wird.
  15. Verfahren gemäß einem der Ansprüche 11 bis 14, dadurch gekennzeichnet, dass das mindestens eine pyrotechnische zusammengesetzte Produkt über ein Spinnen oder Kalandrieren erhalten wird.
EP14809915.3A 2013-11-22 2014-11-21 Pyrotechnisches zusammengesetztes produkt mit unvernetztem bindemittel und verfahren zur herstellung davon Active EP3071537B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PL14809915T PL3071537T3 (pl) 2013-11-22 2014-11-21 Kompozytowy wyrób pirotechniczny z nieusieciowanym lepiszczem i sposób jego wytwarzania

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1302707A FR3013705B1 (fr) 2013-11-22 2013-11-22 Produit pyrotechnique composite a liant non reticule et son procede de preparation
PCT/FR2014/000250 WO2015075327A1 (fr) 2013-11-22 2014-11-21 Produit pyrotechnique composite a liant non reticule et son procede de preparation

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EP3071537A1 EP3071537A1 (de) 2016-09-28
EP3071537B1 true EP3071537B1 (de) 2017-08-16

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US (1) US20160289133A1 (de)
EP (1) EP3071537B1 (de)
CA (1) CA2930486A1 (de)
FR (1) FR3013705B1 (de)
PL (1) PL3071537T3 (de)
WO (1) WO2015075327A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3028853B1 (fr) * 2014-11-21 2016-12-30 Pyroalliance Cordeaux detonants de decoupe et leur preparation
FR3028852B1 (fr) * 2014-11-21 2017-01-06 Herakles Produits explosifs composites de faible epaisseur et leur preparation

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3151010A (en) * 1955-02-11 1964-09-29 Phillips Petroleum Co Method of preparing a solid composite propellant
US3026672A (en) * 1959-06-29 1962-03-27 Phillips Petroleum Co Composite propellant containing burning rate depressant and method of use
FR1409203A (fr) 1961-01-10 1965-08-27 Aerojet General Co Mélanges propulsifs à base de polyuréthanes
US3577289A (en) * 1968-02-12 1971-05-04 Jacque C Morrell Composite high energy solid rocket propellants and process for same
GB1316692A (en) 1970-05-04 1973-05-09 North American Rockwell Monomers polymerisable to form binders for explosive and propellant compositions and polymers and compositions formed therefrom
FR2109102A5 (en) 1970-10-01 1972-05-26 France Etat Resin bound explosive - contg rounded particles of explosive
FR2159826A5 (en) 1971-11-12 1973-06-22 Voith Gmbh Extruding thermosetting resins - eg polyesters with fibrous fillers to give stable profiles
FR2268770A1 (en) 1974-04-24 1975-11-21 Commissariat Energie Atomique Resin coated explosive compsn - prepd by liquid phase prodn of granules which are then compressed and crosslinked by heating
DE3010052C2 (de) 1980-03-15 1982-09-09 Friedrich-Ulf 8899 Rettenbach Deisenroth Verfahren zur Herstellung von kunststoffgebundenen Explosivstoffen
JPS56160395A (en) 1980-03-20 1981-12-10 Hercules Inc Crosslinked propellant
US4381958A (en) 1980-08-07 1983-05-03 Hercules Incorporated Triaminoguanidine nitrate-containing propellants
JPS609996B2 (ja) 1980-10-07 1985-03-14 日本油脂株式会社 ニトラミン系コンポジツト推進薬組成物
US4335231A (en) * 1981-04-03 1982-06-15 Uniroyal, Inc. Sulfur curable millable polyurethane gum
FR2577919B1 (fr) 1985-02-27 1987-02-20 Poudres & Explosifs Ste Nale Procede de fabrication sans solvant de produits pyrotechniques composites a liant thermodurcissable et produits ainsi obtenus, notamment poudres propulsives composites
US5500060A (en) * 1986-07-04 1996-03-19 Royal Ordnance Plc Energetic plasticized propellant
US4919737A (en) * 1988-08-05 1990-04-24 Morton Thiokol Inc. Thermoplastic elastomer-based low vulnerability ammunition gun propellants
US5248731A (en) * 1989-03-20 1993-09-28 Reeves Bros. Inc. Calenderable thermoplastic compositions containing millable linear polyurethanes
DE69905398T2 (de) * 1998-11-12 2003-06-12 Alliant Techsystems Inc Herstellung von energetischen thermoplastischen elastomeren die oligomere urethanbindungen enthalten
US20050267245A1 (en) * 2003-03-18 2005-12-01 Sandusky Donald A Alloy blends of polyurethane and rubber
US8501390B2 (en) * 2006-06-27 2013-08-06 Xiper Innovations, Inc. Laser engravable flexographic printing articles based on millable polyurethanes, and method

Non-Patent Citations (1)

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

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Publication number Publication date
FR3013705B1 (fr) 2016-07-01
WO2015075327A1 (fr) 2015-05-28
EP3071537A1 (de) 2016-09-28
FR3013705A1 (fr) 2015-05-29
CA2930486A1 (fr) 2015-05-28
US20160289133A1 (en) 2016-10-06
PL3071537T3 (pl) 2018-02-28

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