EP0218511A1 - 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
EP0218511A1
EP0218511A1 EP86402055A EP86402055A EP0218511A1 EP 0218511 A1 EP0218511 A1 EP 0218511A1 EP 86402055 A EP86402055 A EP 86402055A EP 86402055 A EP86402055 A EP 86402055A EP 0218511 A1 EP0218511 A1 EP 0218511A1
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EP
European Patent Office
Prior art keywords
binder
adhesion agent
composition according
propellant
agent
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.)
Granted
Application number
EP86402055A
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English (en)
French (fr)
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EP0218511B1 (de
Inventor
Bernard Finck
Gérard Doriath
Jean-Pierre Martenot
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.)
Safran Ceramics SA
Original Assignee
Societe Nationale des Poudres et Explosifs
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Publication of EP0218511A1 publication Critical patent/EP0218511A1/de
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Publication of EP0218511B1 publication Critical patent/EP0218511B1/de
Expired legal-status Critical Current

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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 properties and feasibility, 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 demold the block thus produced, which adheres directly to it, we then say that we have a molded 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.
  • v is generally considered the product S m m .e, by analogy to the product Sm. ⁇ used for elastic materials and which represents the maximum energy admissible by the material without undergoing irreversible damage.
  • the mechanical properties of a propellant are largely determined by the nature of the binder, the degree of polymerization and crosslinking thereof. It is therefore customary to add polyols to the composite propellants with a polyurethane binder. short 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.
  • MAPO derivatives have also been proposed, in particular the compounds resulting from the reaction of MAPO with a carboxylic acid.
  • 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 (I): in which: R 1 , 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.
  • the 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 weight concentration of aminoaziridinylphosphine oxide compound in the propellant composition is between 0.5 and 3% and preferably between 0.5 and 1.5% by 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 azoleic acid
  • polyethers with hydroxyl endings prepared from polyoxytetramethylene glycol, polyoxypropylene 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 sold 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), sorting ( isocyanato-6) -, 3.5 biuret (marketed by the Company BAYER AG under the name Desmodur N100) methylene-4,4 'bis (cyclohexyldiisocyanate) (MDCI), or the like.
  • TDI toluene diisocyanate
  • HMDI hexamethylene diisocyanate
  • DDI dimeryldiisocyanate
  • IPDI isophorone diisocyanate
  • sorting isocyanato-6) -, 3.5 biuret (marketed by the Company BAYER AG under the name Desmodur N100) methylene-4,4 'bis (cyclohex
  • 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 cyclotrimethylenetrinitramine or hexogen (RDX), cyclo-tetramethylenetetranitramine or octogen (HMX), or pentaerythritol tetranitrate (PETN), bu analog.
  • RDX cyclotrimethylenetrinitramine or hexogen
  • HMX cyclo-tetramethylenetetranitramine or octogen
  • PETN pentaerythritol tetranitrate
  • 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 1 , 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 (I): 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 bismethylaziridinylmethylaminophosphine 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.
  • the dihaloaminophosphine can be obtained by reacting a phosphorus oxyhalide with 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, summarily, in adding into the mixture of polyols, in the present example 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.
  • the composition contains:
  • 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 (e m ).
  • compositions are produced according to the method of Example 1 with the same binder, but the propellant has the following composition:
  • Example 1 As for 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 a binder-filler adhesion agent tri (methylaziridinyl) phosphine oxide (MAPO) ) and bis (aziridinyl) methylaminophosphine oxide (BAPO) in a concentration equal to 2% by weight relative to the mass of the binder.
  • MAPO methylaziridinyl) phosphine oxide
  • BAPO bis (aziridinyl) methylaminophosphine oxide
  • 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.
  • a propellant composition is produced according to the method of Example 1 with a binder of the following weight 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 centers between 0.5 and 1.5%.
  • the propellant has the following weight composition: Furthermore, swelling tests with binders loaded with aluminum or not have shown that the binder-alumininum adhesion is greater in the presence of an adhesion agent according to the invention.
  • the binder-filler adhesion agent of the invention namely an aminoaziridinylphosphine oxide, makes it possible to obtain composite propellants with improved mechanical properties, 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)
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
FR8513871 1985-09-19
FR8513871A FR2587329B1 (fr) 1985-09-19 1985-09-19 Agent d'adhesion liant-charge et composition propulsive contenant cet agent d'adhesion

Publications (2)

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

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EP86402055A Expired EP0218511B1 (de) 1985-09-19 1986-09-19 Bindemittel-Füllstoff-Adhäsionsmittel und dieses Adhäsionsmittel enthaltende Treibstoffzusammensetzung

Country Status (13)

Country Link
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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0314547A1 (de) * 1987-10-29 1989-05-03 GIAT Industries Treibladung für flügelstabilisierte Geschossmunition sowie Verfahren zu ihrer Herstellung
CN108117466A (zh) * 2017-12-22 2018-06-05 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

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
US4000023A (en) * 1968-12-09 1976-12-28 Aerojet-General Corporation Bonding agents for polyurethane

Family Cites Families (8)

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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
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

Patent Citations (4)

* 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
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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0314547A1 (de) * 1987-10-29 1989-05-03 GIAT Industries Treibladung für flügelstabilisierte Geschossmunition sowie Verfahren zu ihrer Herstellung
FR2622687A1 (fr) * 1987-10-29 1989-05-05 France Etat Armement Chargement propulsif pour munition comportant un projectile empenne ainsi que son procede de realisation
CN108117466A (zh) * 2017-12-22 2018-06-05 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

Also Published As

Publication number Publication date
JPS6289779A (ja) 1987-04-24
FR2587329B1 (fr) 1989-05-12
AU6290786A (en) 1987-03-26
AU581344B2 (en) 1989-02-16
ZA867108B (en) 1987-05-27
BR8604477A (pt) 1987-06-16
ES2015620A6 (es) 1990-09-01
NO164893C (no) 1990-11-28
CA1285771C (en) 1991-07-09
FR2587329A1 (fr) 1987-03-20
US4747891A (en) 1988-05-31
DE3665447D1 (en) 1989-10-12
NO863707L (no) 1987-03-20
JPH0759694B2 (ja) 1995-06-28
IN166668B (de) 1990-06-30
EP0218511B1 (de) 1989-09-06
NO164893B (no) 1990-08-20
NO863707D0 (no) 1986-09-17
IL79922A (en) 1990-11-05

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Effective date: 20060919