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EP1932817A1 - Propergol constitué de nitratoéthyle nitramine pour systèmes de sécurité pour automobiles - Google Patents

Propergol constitué de nitratoéthyle nitramine pour systèmes de sécurité pour automobiles Download PDF

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Publication number
EP1932817A1
EP1932817A1 EP06405515A EP06405515A EP1932817A1 EP 1932817 A1 EP1932817 A1 EP 1932817A1 EP 06405515 A EP06405515 A EP 06405515A EP 06405515 A EP06405515 A EP 06405515A EP 1932817 A1 EP1932817 A1 EP 1932817A1
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cas
weight
propellant according
propellant
binder
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EP06405515A
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German (de)
English (en)
Inventor
Hanspeter Andres
Jacques Rebetez
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Nitrochemie Wimmis AG
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Nitrochemie Wimmis AG
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Priority to EP06405515A priority Critical patent/EP1932817A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
    • C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
    • C06D5/06—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets by reaction of two or more solids
    • 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
    • C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive

Definitions

  • An extruded propellant for use in automotive safety systems comprising a binder, a plasticizer of the chemical group of nitratoethylnitroamines, and an oxidizer.
  • Gas generators are today used in large quantities, among other things for safety devices for vehicles (airbag, belt tensioners, activators, etc.). This is located in an encapsulation an energetic propellant (also known as fuel or propellant), which is ignited in an emergency by an igniter and which generates the necessary amount of gas to inflate, for example, the airbag or trigger the mechanics of a belt tensioner. The detonator is initiated by an external accelerometer.
  • energetic propellant also known as fuel or propellant
  • the detonator is initiated by an external accelerometer.
  • Such gas generators are available in different embodiments. By way of example, reference is made to the gas generator device US 5,062,365 directed.
  • oxygen balance is understood to mean that amount of oxygen in% by weight which is free or required in the case of complete conversion of a compound or composition into CO 2 , H 2 O, Al 2 O 3, etc.
  • oxygen balance is understood to mean that amount of oxygen in% by weight which is free or required in the case of complete conversion of a compound or composition into CO 2 , H 2 O, Al 2 O 3, etc.
  • the proportions of toxic nitrogen oxides (NO x ) and carbon monoxide (CO) are below the specified limit values of 80 and 461 ppm in the vehicle compartment only when the oxygen balance is balanced or slightly underbalanced.
  • a propellant During the entire life cycle of a motor vehicle, a propellant must remain fully functional. Particularly in the case of new pedestrian protection applications in the hot engine compartment, very high thermal stability is required. The required temperature storage of up to 1000 h at 90 and 107 ° C can only be met by consistent elimination of thermally labile compounds and incompatibilities of a composition.
  • the oxygen sub-balancing must be compensated by a high proportion of oxidizing agents.
  • a gas-generating mixture for pretensioner systems based on a thermally stabilized binder an oxidizing agent and optionally a chlorine-neutralizing additive is described as the main components.
  • cellulose derivatives with common inert and energetic plasticizers are known as thermally stabilized binders.
  • the proportion of the binder is 7-30 wt.%, That of the oxidizing agent in the range 70-93 wt.%.
  • derivatives of diphenylamine, aromatic urea compounds, resorcinol and mixtures thereof are added proportionally to 1.2% by weight.
  • the plasticizers used are predominantly inert phthalates, citrates, adipates and glycolates up to 5% by weight.
  • the only known energetic plasticizer is diethylene glycol dinitrate, a pure nitrate ester compound with moderate stability properties.
  • Nitratoethylnitroamines have a nitramine and a nitrate ester functionality as well as an alkyl radical which can be adapted to the polymer's polarity to optimize plasticiser properties.
  • the three most important representatives are methyl-nitratoethylnitroamine (1), ethyl-nitratoethylnitroamine (2) and butyl-nitratoethylnitroamine (3).
  • EP-A-0 470 865 describes extruded airbag blown propellants based on cellulose acetate butyrate with butyl-nitratoethylnitroamine containing at least 50% by weight of basic copper nitrate.
  • the propellant contains guanidine nitrate and / or cobalt (II) hexamine nitrate.
  • the proportion of the binder is between 5 and 20 wt.%.
  • the combustion of basic copper nitrate initially produces liquid copper, and after cooling below 1000 ° C solid copper oxide. However, with a copper content of up to 25% by weight, the gas yield is considerably reduced.
  • cobalt (II) hexamine nitrate which can also form toxic solids after combustion. None is reported about the thermal stability of the compositions in relation to the requirements for safety systems in motor vehicles.
  • the object of the invention is to provide a blowing agent associated with the technical field mentioned above, which is particle-free and environmentally harmless burnable at high gas yield and also has a high thermal long-term stability at elevated temperatures.
  • the propellant contains a binder, a plasticizer of the chemical group of nitratoethyl nitroamines and an oxidizer free of heavy metals.
  • heavy metal-free is understood to mean that the blowing agent contains less than 100 ppm (parts per million) of heavy metals.
  • Suitable binders are a variety of polymeric materials, inert variants as they are used in the plastics industry and energetic variants as they are known from military technology.
  • inert binders are cellulose acetate (CA, CAS #: 9004-35-7), cellulose acetate butyrate (CAB, CAS #: 9004-36-8), sodium carboxymethylcellulose (Na-CMC, CAS #: 9004-32-4), hydroxyethylcellulose (HEC, CAS #: 9004-62-0), hydroxypropylcellulose (HPC, CAS #: 9004-64-2), methylcellulose (MC, CAS #: 9004-67-5 Ethylcellulose (EC, CAS #: 9004-57-3), ethyl 2-hydroxyethylcellulose (EHC, CAS #: 9004-58-4), carboxymethylethylcellulose (CMEC, CAS #: 37205-99- 5), starch (CAS #: 9005-25-8), guar gum (CAS #: 9000-30-0
  • energetic binders include nitrocellulose (NC, CAS #: 9004-70-0); Glycidyl azide polymer (GAP, CAS #: 143178-24-9), polyvinyl nitrate (PVN), 3-nitratomethyl-3-methyl-oxetane (poly-NIMMO; CAS #: 84051-81-0), bis-nitrato-methyl Oxetane (poly-BNMO), poly-3-azidomethyl-3-methyl-oxetane (poly-AMMO; CAS #: 90683-29-7), poly (3,3-bis-ethoxymethyl-oxetane (poly -BEMO), poly-3,3-bis-azidomethyl-oxetane (poly-BAMO; CAS #: 17607-20-4), poly-2,2-bisazidomethyl-1,3-propanediol glutarate (PAP-G), Dinitropropanediol polyadipate (PAD
  • binder materials which can be plastically deformed in a solvent process or by heating with addition of plasticizer.
  • Inert and energetic cellulose derivatives have proven to be suitable; Particularly suitable are cellulose acetate, cellulose acetate butyrate, hydroxypropyl cellulose and nitrocellulose. All of these binder materials are available in finely ground form and can be processed using non-aqueous solvents; which is particularly suitable for the processing of water-sensitive oxidants.
  • Particularly advantageous is a mixture of cellulose acetate butyrate and nitrocellulose, which complement each other in terms of mechanical properties.
  • the proportion of the binder is chosen as low as possible due to its negative oxygen balance. However, in order to bind high solids content, a binder content of 5 to 30% has been found to be suitable. A proportion between 10 and 25% by weight has proven particularly suitable.
  • the proportion of the energetic binder is preferably between 1 and 15 wt.%, Particular preference is given to proportions between 2 and 10 wt.%.
  • binder used stabilizing and softening additives must be added.
  • the former to ensure a sufficient long-term stability at high temperatures for energetic cellulose derivatives and energetic plasticizers and to make the latter easier to process.
  • Suitable stabilizers for nitrate esters are in particular derivatives of diphenylurea and diphenylamine.
  • Typical conventional stabilizers for energetic cellulose derivatives are, for example, acardite I (CAS #: 605-54-3), acardite II (CAS #: 13114-72-2), acardite III (CAS #: 18168-01- 9), diphenylamine (CAS #: 122-39-4), 2-nitrodiphenylamine (CAS #: 119-75-5), triphenylamine (CAS #: 603-34-9), resorcinol (CAS #: 108-46-3), Centralit-I (CAS #: 85-98-3) and Centralit-II (CAS #: 611-92-7).
  • Akardit II has been found to be a stabilizer of nitrocellulose, since Akardit II in contrast to diphenylamine forms virtually no carcinogenic N-nitrosamines during aging and generally shows a higher stabilizing effect.
  • a stabilizer content of 0.5 to 5 wt.% Based on the energetic components used. In the present case, a higher content up to 20 wt.% Has proven to be suitable.
  • Optimal is a proportion of 3 to 15 wt.% Based on the nitrate ester compounds used.
  • inert plasticizers are typically suitable polyoxo compounds, as they are known in the plastics industry and are industrially used for plasticizing mass plastics. Examples of these are, for example, a polyester or a polyether compound having an average molecular weight of 100-10,000 g / mol. Preference is given to citrate esters, adipic acid esters, sebacic acid esters and phthalic acid esters (or hydrogenated cyclohexyl derivatives thereof) or combinations thereof.
  • Examples include acetyl triethyl citrate (CAS #: 77-89-4), triethyl citrate (CAS #: 77-93-0), tri-n-butyl citrate (CAS - #: 77-94-1), tributyl acetyl citrate ( 77-90-7), acetyltri-n-butyl citrate (CAS #: 77-90-7), acetyltri-n-hexyl citrate (CAS #: 24817-92-3), n-butyryltri-n-hexyl citrate (CAS - #: 82469-79-2), di-n-butyl adipate, diisopropyl adipate (CAS #: 6938-94-9), diisobutyl adipate (CAS #: 141-04-8), di- ethylhexyl adipate (CAS #: 103-23-1), nonyl undecyl adipate, n-decyl n
  • inert plasticizing additives are also available under the following trade names: Hexamoll Dinch from BASF, Citroflex types from Reilly-Morflex Inc., Greensboro, North Carolina USA, and others A-2, A-4, A-6, C- 2, C-4, C6, B-6, Paraplex types from CP Hall Co. Chicago, Illinois USA, including G25, G30, G51, G54, G57, G59, Santicizer types from Ferro Corporation, Cleveland, Ohio USA, 261 . 278 , Palatinol types of BASF, Germany.
  • Energetic plasticizers are typically used in propellant powders to accelerate projectiles; On the one hand, these can be distributed homogeneously over the grain matrix, as in the case of bivalent and polybasic propellant charge powders, or, on the other hand, they can be concentrated in the near-surface layers after a surface treatment. Examples of this are e.g. aliphatic nitrate esters, nitro compounds, nitramines and azides or combinations thereof having an average molecular weight of 100-1000 g / mol.
  • NNL nitroglycerin
  • DEGN diethylene glycol dinitrate
  • TEGN triethylene glycol dinitrate
  • EGDN ethylene glycol dinitrate
  • BTTN 1,2,4-butanetriol trinitrate
  • MTN propanediol trinitrate
  • BDNPA bis (2,2-dinitropropyl) acetal
  • BDNPA bis (2,2-dinitropropyl) acetal
  • BDNPA 2,4-Dintro-2,4-diazapentane
  • DNDA 2,4-Dintro-2,4-diazapentane
  • cellulose derivatives particularly suitable for use with cellulose derivatives are the energetic plasticizers due to their weakly negative oxygen balance.
  • the Nitratoethylnitroamine have been found because they have shown an additional stabilizing effect in addition to the plasticizing properties, the complete combustibility and the high gas yield.
  • Butyl-Nitratoethylnitroamin is particularly suitable due to the strongest plasticizing effect and the low flame temperature.
  • the proportion of plasticizer is between 1 and 10 wt.%, In particular, proportions of 2 to 5 wt.% Prove to be optimal.
  • oxidizing agents are ammonium, alkali metal and alkaline earth metal salts of hydrochloric acid, perchloric acid, chromic acid, nitric acid and nitrous acid.
  • examples include barium chlorate (CAS #: 13477-00-4), ammonium perchlorate (CAS #: 7790-98-9), potassium perchlorate (CAS #: 7778-74-7), sodium perchlorate (CAS #: 7601- 89-0), barium chlorate (CAS #: 10294-40-3), ammonium nitrate (CAS # 6484-52-2), barium nitrate (CAS #: 10022-31-8), potassium nitrate (CAS #: 7757-79-1), copper nitrate (CAS #: 3251-23-8); Sodium nitrate (CAS #: 7361-99-4), strontium nitrate (CAS #: 10042-76-9), iron oxide (CAS #: 1309-37-1 and 1317-61-9, respectively).
  • ammonium perchlorate and / or ammonium nitrate are particularly suitable.
  • ammonium perchlorate and / or ammonium nitrate are particularly suitable.
  • Particularly suitable are mixtures of the ammonium nitrate with potassium nitrate, which demonstrably suppresses the critical phase transformation of the ammonium nitrate by the processing method used.
  • the average particle diameter of the oxidizing agent is preferably less than 100 .mu.m, particularly preferred mean particle sizes below 50 .mu.m. This facilitates the incorporation into the binder material and the subsequent extrusion, in addition it increases the burning rate of the blowing agent.
  • the proportion of the oxidizing agent is preferably between 70 and 95 wt.%. Particular preference is given to using fractions of between 75 and 85%. This high proportion of oxidizer makes it possible to compensate for the negative oxygen balance of the remaining blowing agent components.
  • the propellant may additionally contain nitrogen-rich compounds to increase the gas yield.
  • nitrogen-rich compounds are guanidine, tetrazole, bitetrazole, tritetrazole, hydrazine, triazine, azodicarbonamide, hydrazodicarbonamides, dicyanamides or nitramine compounds and combinations thereof.
  • Examples include guanidine nitrate (CAS #: 506-93-4), nitroguanidine (CAS #: 556-88-7), 1,1-diamino-2,2-dinitroethylene (FOX-7), N-guanyl urea dinitramide ( FOX-12), 5-aminotetrazole (CAS #: 5378-49-4), hexogen (RDX, CAS # 121-82-4 :), octogen (HMX, CAS # 2691-41-0) and ethylenedinitramine (EDNA, CAS #: 505-71-5).
  • the nitramine compounds which are produced in large quantities for explosives are suitable. Hexogen proves to be particularly suitable.
  • the burning rate can be significantly increased by the incorporation.
  • the suitable range of use is between 1 and 30% by weight; Preferably, the range is from 5 to 20 wt.%.
  • the propellant may contain chlorine-neutralizing additives.
  • Chlorine-neutralizing additives are added, in particular, to chlorate- and perchlorate-containing formulations for neutralizing the hydrochloric acid in the combustion clouds.
  • Suitable chlorine-neutralizing additives are found among the alkali and alkaline earth salts. These can be used individually or in combination.
  • Examples include sodium carbonate (CAS #: 5968-11-6), sodium nitrate (CAS #: 7631-99-4), sodium oxide (CAS #: 1313-59-3), sodium oxalate (CAS #: 62- 76-0), strontium carbonate (CAS #: 1633-05-2), strontium silicate (CAS #: 13451-00-8), strontium oxide (CAS #: 1314-11-0), strontium oxalate (CAS #: 814-95-9), stontrium peroxide (CAS #: 1314-18-7), calcium silicate (CAS #: 1344-95-2), calcium nitrate (CAS #: 10124-37-5), calcium oxalate (CAS).
  • Oxalate compounds in particular are suitable as chlorine-neutralizing additives because of their complete combustibility and low flame temperature.
  • Particularly suitable is sodium oxalate due to the low molecular weight of the cation.
  • the range of use depends on the percentage of chlorate and / or perchlorate salts. A proportion of between 5 and 50% by weight is suitable. Shares of between 5 and 20% by weight are particularly suitable.
  • a propellant may contain additives for reducing the combustion flame.
  • additives preferably originate from the group of sulfates, nitrates and / or cryolites. Examples are sodium sulfate (CAS #: 7757-82-6), potassium sulfate (CAS #: 7778-80-5), barium nitrate (CAS #: 10022-31-8), and sodium aluminum fluoride (CAS #: 15096-52 -3).
  • the proportion is preferably in the range of 0.1-5 wt.%, Particularly preferably in the range of 1 to 2 wt.%.
  • the blowing agent can be polished to improve the flowability graphite (CAS #: 7782-42-5). This method is common for nitrocellulose-based blowing agents; As a result, the bulk material is electrically conductive and minimizes the risk of electrostatic ignition. Typically, a graphite content of between 0.01 to 1 wt.% Is polished; optimally, the proportion is between 0.02 to 0.5 wt.%. In addition to graphite, the blowing agent can be further polished with additives such as primers.
  • the blowing agents of the present invention can be prepared without limitation by conventional methods.
  • all components binder, stabilizers, plasticizers, oxidizers and other additives can be mixed with suitable solvents to form a homogeneous dough.
  • water-sensitive oxidants such as ammonium nitrate and / or perchlorate
  • the dough may preferably be extruded through a given die and cut to length. The final shape is obtained after removal of the solvents and any postpolymerization.
  • extruded forms can be grains or perforated grains. For perforated grains, either 1, 7 or 19 holes are common.
  • the decisive factor for the burnup is the wall thickness, defined as the shortest burning distance (eg between hole and outer wall, etc.). Another type of processing by means of melting of the binder, incorporation of the solids and subsequent continuous extrusion is explicitly not excluded.
  • the size of the grains depends on the application.
  • the wall thickness is usually between 0.2 to 3 mm, preferably wall thicknesses in the range 0.5 to 2 mm.
  • the wall thickness is usually between 0.5 and 5 mm, preferably wall thicknesses in the range 1 to 3 mm.
  • the outer diameter of the perforated grains is in a preferred variant of the order of the length of the grains. More preferably, the length is about 1.1 times the outer diameter of the grain.
  • the manufactured propellant can now be encapsulated in a gas generator and provides at initiation the necessary amount of gas to inflate, for example, the airbag or trigger the mechanics of the belt tensioner.
  • Fig. 1 For illustration, the oxygen balance, the flame temperature and the gas yield of each of six inert and energetic plasticizers are listed in tabular form. The flame temperature and gas yield were determined by thermodynamic calculations.
  • the inert plasticizers with oxygen balances of -300 to -150% have gas yields of not more than 750 ml / g.
  • the gas yields are in the range 800-1000 ml / g.
  • Butyl-NENA shows the highest gas yield with an acceptable oxygen balance and low temperatures for energetic softeners.
  • a conventional monobasic propellant for belt tensioner applications is prepared as follows: 97% by weight of nitrocellulose, 2% by weight of acardite II and 1% by weight of sodium oxalate are placed in a kneader in a solvent-wet state. The mass is kneaded in about 2 hours until a consistent dough is formed. Subsequently, the dough is extruded through dies and cut to length. After complete removal of the solvent, the bulk material is graphitized and sieved. The finished 1-hole powder grains have an outer diameter of 1.4 mm, a hole diameter of 0.2 mm, a length of 2.2 mm, a gravimeter of 981 g / l and an explosion heat of 3911 J / g. The average vivacity of the propellant between 30-80% of the maximum pressure is 31 ⁇ 10 -2 / bar ⁇ s.
  • a plastic-bound propellant for belt tensioner applications is manufactured as follows: 14% by weight of cellulose acetate butyrate, 4% by weight of alcohol-wet nitrocellulose, 5% by weight of sodium oxalate, 3% by weight of butyl NENA and 1% by weight of acardite II are charged in a kneader and mixed for 5 minutes. Subsequently, 56% by weight of ammonium perchlorate and 6% by weight of hexogen are added in a solvent-moist state. The mass is kneaded in about 2 hours until a consistent dough is formed. The dough is then extruded and cut to length. After complete removal of the solvent, the bulk material is graphitized and sieved.
  • the finished powder grains have an outer diameter of 1.1 mm, a length of 1.3 mm, a gravimeter of 946 g / l and an explosion heat of 5177 J / g.
  • the average vivacity of the propellant between 30-80% of the maximum pressure is 40.10 -2 / bar ⁇ s.
  • Example A has a carbon monoxide content of 7362 ppm; the plastic-bound propellant (Example B) is 1628 ppm.
  • Example A In each case 1000 mg of the blowing agents from Examples A and B were used in a microgas generator with Squib ignition. After thermal aging, the weight of the monobasic propellant (Example A) is reduced by 17% after 408 h at 107 ° C due to the autocatalytic decomposition; in the case of the plastic-bonded propellant (Example B) by 2% after 408 h at 107 ° C. As a result of aging, the maximum pressure is reduced by 30% (propellant from Example A) and 7% (propellant from Example B).
  • a plastic-bound propellant for airbag applications is manufactured as follows: 13% by weight of cellulose acetate butyrate, 2% by weight of tributyl citrate and 0.3% by weight of acardite II are charged in a kneader and mixed for 5 minutes. Subsequently, 76% by weight of ammonium nitrate and 9% by weight of potassium nitrate are added in a solvent-moist manner. The mass is kneaded for about 2 hours until a consistent dough is formed. The dough is then extruded and cut to length. After complete removal of the solvent, the bulk material is graphitized and sieved.
  • the finished 1-hole powder grains have an outer diameter of 2.2 mm, a hole diameter of 0.7 mm, a length of 3.0 mm, a gravimeter of 777 g / l and an explosive heat of 3982 J / g.
  • the average vivacity of the propellant between 30-80% of the maximum pressure is 9.1 ⁇ 10 -2 / bar ⁇ s.
  • Example C a plastic-bonded blowing agent for airbag applications was manufactured. Butyl NENA was used instead of the inert plasticizer tributyl citrate.
  • the finished 1-hole powder grains have an outer diameter of 2.1 mm, a hole diameter of 0.8 mm, a length of 3.0 mm, a gravimeter of 749 g / l and an explosion heat of 4054 J / g.
  • the average vivacity of the propellant between 30-80% of the maximum pressure is 9.6 ⁇ 10 -2 / bar ⁇ s.
  • Example C has a carbon monoxide content of 872 ppm; the propellant with butyl-NENA (Example D) is 566 ppm.
  • blowing agent is based on the novel combination of a plasticizer from the family of nitratoethylnitroamine and a heavy metal-free oxidizer. Due to the given during production extrudability can be formed with the blowing agent grains with and without perforation with any desired dimension. This allows use in applications with a wide variety of burn behavior.

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EP06405515A 2006-12-12 2006-12-12 Propergol constitué de nitratoéthyle nitramine pour systèmes de sécurité pour automobiles Withdrawn EP1932817A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011090375A1 (fr) * 2010-01-19 2011-07-28 Clearspark, Llc Procédé de préparation d'une composition pyrotechnique et charge associée
EP2388244A1 (fr) * 2010-05-18 2011-11-23 Diehl BGT Defence GmbH & Co.KG Charge propulsive
JP2012188340A (ja) * 2011-03-09 2012-10-04 Res Inst Of Natl Defence 鈍感性固体推進剤組成物
WO2015082845A1 (fr) * 2013-12-05 2015-06-11 Herakles Propergols composites stabilises
CN111433172A (zh) * 2018-01-17 2020-07-17 Arc汽车有限公司 非硝酸铵基推进剂
CN114956916A (zh) * 2022-05-23 2022-08-30 西安近代化学研究所 一种聚叠氮缩水甘油醚复合物及其制备方法

Citations (8)

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EP0553476A1 (fr) * 1991-12-27 1993-08-04 Hercules Incorporated Propergol composite sans chlore pour fusée
WO1997007080A1 (fr) * 1995-08-11 1997-02-27 Alliant Techsystems Inc. Explosif utilisable pour la securite automobile
EP0825074A2 (fr) * 1996-08-23 1998-02-25 Trw Inc. Gonfleur pour sac de sécurité gonflable
WO2001010677A2 (fr) * 1999-08-09 2001-02-15 Atlantic Research Corporation Generateur de gaz destine a expulser les substituts de halon
US20010017175A1 (en) * 1997-11-12 2001-08-30 Michael G. Mangum Air bag inflator
EP1205459A1 (fr) * 1999-06-17 2002-05-15 Daicel Chemical Industries, Ltd. Composition contenant une substance generatrice de gaz destinee a un dispositif de mise en tension
US6468370B1 (en) * 2000-04-19 2002-10-22 Trw Inc. Gas generating composition for vehicle occupant protection apparatus
US6875295B2 (en) * 2001-12-27 2005-04-05 Trw Inc. Cool burning gas generating material for a vehicle occupant protection apparatus

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0553476A1 (fr) * 1991-12-27 1993-08-04 Hercules Incorporated Propergol composite sans chlore pour fusée
WO1997007080A1 (fr) * 1995-08-11 1997-02-27 Alliant Techsystems Inc. Explosif utilisable pour la securite automobile
EP0825074A2 (fr) * 1996-08-23 1998-02-25 Trw Inc. Gonfleur pour sac de sécurité gonflable
US20010017175A1 (en) * 1997-11-12 2001-08-30 Michael G. Mangum Air bag inflator
EP1205459A1 (fr) * 1999-06-17 2002-05-15 Daicel Chemical Industries, Ltd. Composition contenant une substance generatrice de gaz destinee a un dispositif de mise en tension
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WO2011090375A1 (fr) * 2010-01-19 2011-07-28 Clearspark, Llc Procédé de préparation d'une composition pyrotechnique et charge associée
US8845833B2 (en) 2010-01-19 2014-09-30 Clearspark, Llc Method for preparing a pyrotechnic composition and charge
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WO2015082845A1 (fr) * 2013-12-05 2015-06-11 Herakles Propergols composites stabilises
FR3014431A1 (fr) * 2013-12-05 2015-06-12 Herakles Propergols composites stabilises
CN111433172A (zh) * 2018-01-17 2020-07-17 Arc汽车有限公司 非硝酸铵基推进剂
CN114956916A (zh) * 2022-05-23 2022-08-30 西安近代化学研究所 一种聚叠氮缩水甘油醚复合物及其制备方法

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