EP0218511B1 - Bindemittel-Füllstoff-Adhäsionsmittel und dieses Adhäsionsmittel enthaltende Treibstoffzusammensetzung - Google Patents

Bindemittel-Füllstoff-Adhäsionsmittel und dieses Adhäsionsmittel enthaltende Treibstoffzusammensetzung Download PDF

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Publication number
EP0218511B1
EP0218511B1 EP86402055A EP86402055A EP0218511B1 EP 0218511 B1 EP0218511 B1 EP 0218511B1 EP 86402055 A EP86402055 A EP 86402055A EP 86402055 A EP86402055 A EP 86402055A EP 0218511 B1 EP0218511 B1 EP 0218511B1
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EP
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Prior art keywords
binder
charges
composition according
composition
propellant
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Expired
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EP86402055A
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English (en)
French (fr)
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EP0218511A1 (de
Inventor
Bernard Finck
Gérard Doriath
Jean-Pierre Martenot
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Safran Ceramics SA
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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
    • C06B23/00—Compositions characterised by non-explosive or non-thermic constituents
    • C06B23/001—Fillers, gelling and thickening agents (e.g. fibres), absorbents for nitroglycerine
    • 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

Definitions

  • the present invention relates to a binder-filler adhesion agent, and a propellant composition with improved mechanical and feasible properties, containing this adhesion agent.
  • It relates more particularly to a binder-filler adhesion agent for a polyurethane binder, and a composite propellant with a polyurethane binder.
  • the composite propellant compositions for rockets, missiles, or for gas generators consist of a generally non-energetic binder and reducing oxidizing charges and possibly reducing charges.
  • the oxidizing charges are generally oxidizing mineral salts such as ammonium perchlorate, for example, while the reducing charges are usually metallic charges and generally aluminum.
  • propellant compositions are preferably used to manufacture large blocks obtained by casting the composition in a mold and then polymerizing the binder.
  • the mold When the mold is formed by the casing of the propellant, it is not necessary to unmold the block thus manufactured, which adheres directly to it, it is then said that there is a molded-glued block. In the other cases where the block is molded in an independent mold then demolded and placed in the casing of the propellant, the block is called free block.
  • the propellant must have high mechanical properties, in particular to allow its manipulation, or to withstand the stresses generated by the deformations, such as the expansion of the casing of the propellant.
  • the mechanical properties of a propellant are characterized by parameters determined by subjecting a test piece thereof to a simple tensile test and by recording the tensile curve shown in the single figure.
  • the mechanical properties of a propellant are largely determined by the nature of the binder, the degree of polymerization and crosslinking thereof. Thus, it is customary to add to the composite propellants with a polyurethane binder, short polyols such as trimethylolpropane to increase the degree of bridging between the polymer chains.
  • the interaction between the binder and the filler is the phenomenon which conditions the cohesion of the propellant.
  • the separation of the charges from the binder causes voids around them which reduce the cohesion of the propellant and therefore weaken its mechanical properties.
  • These detachments can be caused in particular during the elongation of the propellant under the effect of the expansion of the casing of the propellant. This phenomenon is irreversible.
  • the most generally used compounds are compounds containing aziridinyl rings and in particular the trimethylaziridinylephosphine oxide known by the acronym MAPO. (see US-A-3,791,888).
  • MAPO derivatives have also been proposed, in particular the compounds resulting from the reaction of MAPO with a carboxylic acid. (see US-A-3,762,972).
  • the object of the present invention is to propose a new compound having improved properties for reinforcing the mechanical properties of the composition and in particular of the bond between the filler and the binder and therefore making it possible to manufacture propellant compositions having improved mechanical properties and feasibility. .
  • the invention provides a binder-filler adhesion agent between one or more fillers and a polyurethane binder, characterized in that said binder-filler adhesion agent is an aminoaziridinylphosphine oxide of general formula (1): in which: R i , R 2 , R 3 , R 4 which may be identical or different, represent the hydrogen atom or a methyl or ethyl radical.
  • R 1 and R 3 represent the hydrogen atom and R 2 , R 4 represent the methyl radical.
  • a subject of the invention is also a composite propellant composition with a binder based on polyurethane resin containing as main components oxidizing charges and optionally reducing charges, at least one binder-filler adhesion agent, characterized in that said agent adhesion is an aminoaziridinylphosphine oxide as defined above.
  • the concentration by weight of aminoaziridinylphosphine oxide compound in the propellant composition is between 0.5 and 3% and preferably between 0.5 and 1.5% of the weight of the binder.
  • the propellant composition may contain polymerization catalysts, combustion catalysts, plasticizers, antioxidants and any ballistic additive commonly used in composite propellants, in usual proportions and well known to those skilled in the art.
  • Polyurethane resins are obtained by condensation of a polyol, generally a diol, with a polyisocyanate.
  • polyesters with hydroxyl endings obtained from diethylene glycol or ethylene glycol and adipic acid or azelaic acid
  • polyethers with hydroxyl endings prepared from polyoxytetramethylene glycol, polyoxy- propylene glycol or the like
  • polybutadienes with hydroxyl endings designated under the acronym PBHT, and called hydroxytelechelic polybutadienes.
  • the polyurethane binder is obtained from a hydroxytelechelic polybutadiene of average molecular weight 1000 to 5000 g having a hydroxyl functionality of between 2 and 3, advantageously close to 2.3.
  • hydroxytelechelic polybutadienes of the invention mention may be made of those marketed by the American company ARCO Chemical Company under the trade names R45M and R45HT.
  • polyisoyanate compounds suitable as crosslinking agent mention may be made, for example, of toluene diisocyanate (TDI), hexamethylene diisocyanate (HMDI), dimeryldiisocyanate (DDI), isophorone diisocyanate (IPDI) , tri (isocyanato-6) -, 3.5 biuret (marketed by the company BAYER AG under the name Desmo-dur N100) methylene-4,4 'bis (cyclohexyldisocyanate) (MDCI), or the like.
  • TDI toluene diisocyanate
  • HMDI hexamethylene diisocyanate
  • DDI dimeryldiisocyanate
  • IPDI isophorone diisocyanate
  • MDCI tri (isocyanato-6) -, 3.5 biuret
  • MDCI methylene-4,4 'bis (cyclohexyldisocyanate)
  • Suitable oxidizing charges are, for example, ammonium perchlorate, potassium nitrate, or the like.
  • the preferred filler of the invention is ammonium perchlorate.
  • nitramines such as cyclotri-methylenetrinitramine or hexogen (RDX), cyclotetramethylenetetranitramine or octogen (HMX), or pentaerythritol tetranitrate (PETN), or the like.
  • the reducing charges suitable for the invention are generally metallic powders such as aluminum, beryllium, zirconium powder or the like.
  • the preferred reducing filler of the invention is aluminum powder.
  • aminoaziridinylphosphine oxide compounds of the invention can be prepared in particular by the following two methods.
  • the first process consists in manufacturing the compound of formula (II): in which: X represents a halogen and R i , R 2 have the above meaning; according to the methods described in American patents 2 606 900 and 3 201 313, then reacting this compound on an amine of formula (III) to obtain the compound of formula (1): in which R 3 , R 4 have the above meaning.
  • the second method consists in carrying out the following reaction:
  • a halogenated acid sensor (X represents a halogen atom, preferably chlorine) such as triethylamine or methyl-2-aziridine.
  • the reaction is carried out at low temperature, of the order of 0 ° C to -5 ° C.
  • the aminoaziridinylphosphine oxide is recovered.
  • This compound is then purified by, for example, distillation under reduced pressure.
  • methyl-BAPO bismethylaziridinyl-methylaminophosphine oxide which for further simplification will be called hereinafter methyl-BAPO
  • a slightly yellow liquid is recovered which crystallizes into a white product, with density 1.0855 kg / dm 3 and point boiling point 115 ° C at 13.3 Pa.
  • Dihaloaminophosphine can be obtained by reaction of a phosphorus oxyhalide on an alkylamine halohydrate.
  • the alkyl aziridine can be obtained by, in particular, the syntheses of Wenker and Gabriel described respectively in the Journal of the American Chemical Society, vol 57 page 2328 (1935) and in Beilstein vol 21 page 1049 (1881).
  • the composite propellant composition is obtained by the usual manufacturing process which consists, roughly. to be added to the polyol mixture, in the present example the hydroxytelechelic polybutadiene, additives such as wetting plasticizers, antioxidants, crosslinking agents, then the reducing charge is introduced. Then, the mixture obtained is poured into a kneader into which will be introduced the oxidizing charge, the crosslinking agent and the various ballistic additives such as the combustion catalysts, as well as the crosslinking catalysts.
  • the propellant thus obtained is then poured to form a block with the desired dimensions and shape.
  • composition was produced without agent reinforcing the binder-filler adhesion, and three other compositions containing respectively in the binder 1% by weight relative to the mass of the binder, of trimethylolpropane, of a condensate of MAPO with the acid. tartaric, and methyl-BAPO. This latter composition corresponds to the invention. (Table Ia)
  • composition according to the invention namely that containing as reinforcing agent mechanical or adhesion properties binder-filler, methyl BAPO, has the lowest viscosity, and secondly that the adhesion agent binder-filler according to the invention is the only one which makes it possible to obtain a composition having a high resistance to stress (S m ) and a greatly increased level of elongation (em).
  • Example 1 As in Example 1, three compositions are produced, the first of which does not contain a binder-filler adhesion agent, and the other two respectively contain, as binder-filler adhesion agent, tri (methylazyridinyl) phosphine oxide (MAPO). ) and bis (aziridinyl) methylaminophosphine oxide (BAPO) in a concentration equal to 2% by weight relative to the mass of the binder. (Table Il.a)
  • the binder-filler adhesion agent in accordance with the present invention makes it possible to obtain propellants having very advantageous mechanical properties, in particular a high tensile strength (S m ) for a level of elongation (e m ) high.
  • the known binder-filler adhesion agent namely MAPO, makes it possible to significantly increase the tensile strength (S m ) of the propellant but tends to decrease the level of elongation of the composition.
  • compositions 12 and 13 are known aziridinyl compounds used in composite propellants.
  • the agent of the invention also has a beneficial effect on the feasibility of the compositions by lowering the viscosity thereof.
  • binder-filler adhesion agent The optimum level of binder-filler adhesion agent must be determined for each composition. However, the results below show that this rate can be between 0.5 and 3.0% by weight of the binder and that the best results are obtained for concentrations between 0.5 and 1.5%.
  • the binder-filler adhesion agent of the invention namely an aminoaziridinylphosphine oxide, makes it possible to obtain composite propellants with properties improved mechanical mechanisms, in particular having an equally high level of elongation for a high tensile strength.
  • this agent makes it possible to increase the feasibility of the propellant blocks by reducing the viscosity of the compositions for the same loading rate.
  • this binder-filler adhesion agent has no effect on the ballistic properties of the propellant and in particular has no influence on the combustion rate and the specific impulse of this one.

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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)
  • Adhesives Or Adhesive Processes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Claims (9)

1. Bindemittel-Füllstoff-Klebmittel für mindestens einen Füllstoff und ein Polyurethan-Bindemittel, gekennzeichnet durch ein Aminoaziridinylphosphinoxid der Formel (1):
Figure imgb0016
in der R" R2, R3 und R4 gleich oder verschieden sind und Wasserstoff oder Methyl oder Ethyl bedeuten.
2. Klebmittel nach Anspruch 1, dadurch gekennzeichnet, daß in Formel (I) R, und R3 Wasserstoff und R2 und R4 Methyl sind.
3. Treibstoffzusammensetzung mit einem Polyurethanbindemittel, oxidierenden und reduzierenden Füllstoffen als Hauptbestandteile und mindestens einem Bindemittel-Füllstoff-Klebmittel, dadurch gekennzeichnet, daß das Klebmittel ein Bindemittel-Füllstoff-Klebmittel nach Anspruch 1 oder 2 ist.
4. Zusammensetzung nach Anspruch 3, dadurch gekennzeichnet, daß die Konzentration an Aminoaziridinylphosphinoxid von 0,5 bis 3 Masse-% des Bindemittels ausmacht.
5. Zusammensetzung nach Anspruch 4, dadurch gekennzeichnet, daß die Konzentration von 0,5 bis 1,5 Masse-% des Bindemittels ausmacht.
6. Zusammensetzung nach einem der Ansprüche 3 bis 5, dadurch gekennzeichnet, daß das Polyurethan-Bindemittel ein Kondensationsprodukt eines Polybutadiens mit endständigen Hydroxylgruppen und eines aromatischen, aliphatischen oder cycloaliphatischen Diisocyanats ist.
7. Zusammensetzung nach einem der Ansprüche 3 bis 6, dadurch gekennzeichnet, daß die oxidierenden Füllstoffe unter Ammoniumperchlorat, Kaliumperchlorat, Natriumperchlorat, Ammoniumnitrat und Kaliumnitrat und die reduzierenden Füllstoffe unter Aluminium, Zirkonium und Beryllium gewählt sind.
8. Zusammensetzung nach einem der Ansprüche 3 bis 7, dadurch gekennzeichnet, daß sie Explosivstoffe, ausgewählt unter Octogen, Hexogen und Pentaerythrittetranitrat enthält.
9. Zusammensetzung nach einem der Ansprüche 3 bis 8, dadurch gekennzeichnet, daß der oxidierende Füllstoff Ammoniumperchlorat und der reduzierende Füllstoff Aluminium ist.
EP86402055A 1985-09-19 1986-09-19 Bindemittel-Füllstoff-Adhäsionsmittel und dieses Adhäsionsmittel enthaltende Treibstoffzusammensetzung Expired EP0218511B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8513871A FR2587329B1 (fr) 1985-09-19 1985-09-19 Agent d'adhesion liant-charge et composition propulsive contenant cet agent d'adhesion
FR8513871 1985-09-19

Publications (2)

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EP0218511A1 EP0218511A1 (de) 1987-04-15
EP0218511B1 true EP0218511B1 (de) 1989-09-06

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US (1) US4747891A (de)
EP (1) EP0218511B1 (de)
JP (1) JPH0759694B2 (de)
AU (1) AU581344B2 (de)
BR (1) BR8604477A (de)
CA (1) CA1285771C (de)
DE (1) DE3665447D1 (de)
ES (1) ES2015620A6 (de)
FR (1) FR2587329B1 (de)
IL (1) IL79922A (de)
IN (1) IN166668B (de)
NO (1) NO164893C (de)
ZA (1) ZA867108B (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2622687B1 (fr) * 1987-10-29 1993-05-28 France Etat Armement Chargement propulsif pour munition comportant un projectile empenne ainsi que son procede de realisation
US5336343A (en) * 1993-04-16 1994-08-09 Thiokol Corporation Vinyl ethers as nonammonia producing bonding agents in composite propellant formulations
US5366572A (en) * 1993-05-20 1994-11-22 Thiokol Corporation Oxazoline bonding agents in composite propellants
FR2722876B1 (fr) * 1994-07-22 1996-09-13 Manurhin Defense Projectile explosif
US6258188B1 (en) * 1999-10-12 2001-07-10 The United States Of America As Represented By The Secretary Of The Army Solid fuel gas generator for ducted rocket engine
CN104845572B (zh) * 2015-05-14 2017-10-31 湖北三江航天红林探控有限公司 装药包覆材料及其制备方法
CN108117466B (zh) * 2017-12-22 2021-02-09 湖北航天化学技术研究所 一种低燃速高能量丁羟推进剂及脂环族二异氰酸酯的应用
CN114591363B (zh) * 2022-02-28 2024-01-23 武汉理工大学 一种多官能度支化磷酸酰胺键合剂、其制备方法及复合固体推进剂

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3791888A (en) * 1961-01-23 1974-02-12 Phillips Petroleum Co Solid propellants prepared from acidic vinylidene polymers using both polyaziridinyl and difunctional aziridinyl curing agents
US3428484A (en) * 1964-10-30 1969-02-18 Dow Chemical Co Method of treating paper with ethylenimine derivatives using a boron trifluoride-amine complex catalyst
US4000023A (en) * 1968-12-09 1976-12-28 Aerojet-General Corporation Bonding agents for polyurethane
US3762972A (en) * 1969-07-30 1973-10-02 Us Army Reaction product of phosphine oxide with carboxylic acids
US3790416A (en) * 1970-07-22 1974-02-05 Hercules Inc Composite propellant including (u) polyfunctional amine
US3932353A (en) * 1970-09-28 1976-01-13 Aerojet-General Corporation Stabilizers for functionally terminated butadiene polymers
US4263070A (en) * 1973-01-17 1981-04-21 Thiokol Corporation Thermally stable gun and caseless cartridge propellants
US4019933A (en) * 1973-07-27 1977-04-26 The United States Of America As Represented By The Secretary Of The Army Pot life extension of isocyanate cured propellants by aziridine compounds
US4427468A (en) * 1976-01-16 1984-01-24 Her Majesty The Queen In Right Of Canada Curable propellant binding systems with bonding agent combination
US4429634A (en) * 1977-01-06 1984-02-07 Thiokol Corporation Adhesive liner for case bonded solid propellant
US4090893A (en) * 1977-10-11 1978-05-23 The United States Of America As Represented By The Secretary Of The Army Bonding agent system for improved propellant aging and low temperature physical properties
US4158583A (en) * 1977-12-16 1979-06-19 Nasa High performance ammonium nitrate propellant

Also Published As

Publication number Publication date
NO863707D0 (no) 1986-09-17
ZA867108B (en) 1987-05-27
BR8604477A (pt) 1987-06-16
FR2587329A1 (fr) 1987-03-20
US4747891A (en) 1988-05-31
IN166668B (de) 1990-06-30
AU6290786A (en) 1987-03-26
JPH0759694B2 (ja) 1995-06-28
ES2015620A6 (es) 1990-09-01
CA1285771C (en) 1991-07-09
NO164893B (no) 1990-08-20
NO863707L (no) 1987-03-20
DE3665447D1 (en) 1989-10-12
AU581344B2 (en) 1989-02-16
FR2587329B1 (fr) 1989-05-12
NO164893C (no) 1990-11-28
EP0218511A1 (de) 1987-04-15
IL79922A (en) 1990-11-05
JPS6289779A (ja) 1987-04-24

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