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EP3115349A1 - Composition pbx - Google Patents

Composition pbx Download PDF

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Publication number
EP3115349A1
EP3115349A1 EP15275169.9A EP15275169A EP3115349A1 EP 3115349 A1 EP3115349 A1 EP 3115349A1 EP 15275169 A EP15275169 A EP 15275169A EP 3115349 A1 EP3115349 A1 EP 3115349A1
Authority
EP
European Patent Office
Prior art keywords
explosive
cross linking
aryl
phenyl
blocking group
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.)
Ceased
Application number
EP15275169.9A
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German (de)
English (en)
Inventor
designation of the inventor has not yet been filed The
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.)
BAE Systems PLC
Original Assignee
BAE Systems PLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BAE Systems PLC filed Critical BAE Systems PLC
Priority to EP15275169.9A priority Critical patent/EP3115349A1/fr
Priority to AU2016290783A priority patent/AU2016290783B2/en
Priority to US15/746,980 priority patent/US11186528B2/en
Priority to ES16741108T priority patent/ES2913650T3/es
Priority to EP16741108.1A priority patent/EP3319928B1/fr
Priority to CA2991169A priority patent/CA2991169C/fr
Priority to PCT/GB2016/052028 priority patent/WO2017006109A1/fr
Publication of EP3115349A1 publication Critical patent/EP3115349A1/fr
Priority to US17/151,554 priority patent/US11753353B2/en
Priority to US17/151,557 priority patent/US11746069B2/en
Ceased 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
    • C06B21/00—Apparatus or methods for working-up explosives, e.g. forming, cutting, drying
    • C06B21/0033—Shaping the mixture
    • C06B21/0058—Shaping the mixture by casting a curable composition, e.g. of the plastisol type
    • 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

  • This invention relates to polymer bonded explosive compositions, their preparation and use.
  • the invention relates to polymer-bonded explosive compositions for munitions.
  • Explosive compositions are generally shaped, the shape required depending upon the purpose intended. Shaping can be by casting, pressing, extruding or moulding; casting and pressing being the most common shaping techniques. However, it is generally desirable to cast explosives compositions as casting offers greater design flexibility than pressing.
  • Polymer-bonded explosives also known as plastic-bonded explosives and PBX
  • PBX plastic-bonded explosives
  • PBX Polymer-bonded explosives
  • the presence of the matrix modifies the physical and chemical properties of the explosive and often facilitates the casting and curing of high melting point explosives.
  • Such explosives could otherwise only be cast using melt-casting techniques.
  • Melt casting techniques can require high processing temperatures as they generally include a meltable binder. The higher the melting point of this binder, the greater the potential hazard.
  • the matrix can be used to prepare polymer-bonded explosives which are less sensitive to friction, impact and heat; for instance, an elastomeric matrix could provide these properties.
  • the matrix also facilitates the fabrication of explosive charges which are less vulnerable in terms of their response to impact, shock, thermal and other hazardous stimuli.
  • a rigid polymer matrix could allow the resulting polymer-bonded explosive to be shaped by machining, for instance using a lathe, allowing the production of explosive materials with complex configurations where necessary.
  • the invention seeks to provide a cast explosive composition in which the stability of the composition is improved.
  • a composition would not only offer improved stability, but also a reduced sensitivity to factors such as friction, impact and heat. Thus, the risk of inadvertent initiation of the explosive is diminished.
  • a precure castable explosive composition comprising an explosive material, a polymerisable binder, a cross linking reagent which comprises at least two reactive groups each of which is protected by a labile blocking group.
  • a labile blocking group to protect the reactive groups of the cross linking reagent allows uniform distribution of the cross linking reagent within the precure composition, thereby allowing control of when the curing reaction may be initiated.
  • the blocking group may be removed such that the reactive groups may be free, so as to allow the cross linking reaction to commence with the polymerisable binder, and permit the formation of a uniform PBX polymeric matrix, when desired.
  • the labile blocking group may on each of the at least two reactive groups on the cross linking reagent, may be the same group, or independently selected.
  • the labile blocking groups may be independently selected so as to be removed at different deblocking temperature, or in response to different external stimuli.
  • the enhanced control of the start of the cross linking reactions allows the recovery of the precure composition in the event of process equipment failure.
  • many tonnes of material would end up solidifying/curing in the reaction vessel, as one the reaction has started it cannot be readily stopped.
  • the delay of the cure reaction allows product quality to be confirmed, before the reaction is allowed to commence, thereby a poor quality composition, may be prevented from being filled into moulds or munitions.
  • the use of labile blocking groups on the reactive groups of the cross linking reagent may reduce the exposure to operators of hazardous cross linking reagents.
  • the polymerisable binder may be partially polymerised with the cross linking reagent, such that at least one of the at least two reactive groups on the cross linking reagent has formed a bond with the polymerisable binder, and at least one of the at least two reactive groups may protected by a labile blocking group, such that on removal of the remaining labile blocking group(s) substantially complete polymerisation with the polymerisable binder may occur.
  • the polymerisable binder and cross linking reagent are partially reacted together to provide a partially polymerised binder-cross linking reagent, wherein at least one of the at least two reactive groups of the cross linking reagent is protected by a labile blocking group.
  • the formation of a partially polymerised polymerisable binder/cross linking reagent may provide a means of increasing homogeneity of the binder in the explosive composition.
  • the partially polymerised polymerisable binder/cross linking reagent may be extracted and purified, to provide a reduced mass of removed labile protecting group in the final cured PBX.
  • the explosive component of the polymer-bonded explosive may, in certain embodiments, comprise one or more heteroalicyclic nitramine compounds.
  • Nitramine compounds are those containing at least one N-NO 2 group.
  • Heteroalicyclic nitramines bear a ring containing N-NO 2 groups. Such ring or rings may contain for example from two to ten carbon atoms and from two to ten ring nitrogen atoms.
  • Examples of preferred heteroalicyclic nitramines are RDX (cyclo-1,2,3-trimethylene-2,4,6-trinitramine, Hexogen), HMX (cyclo-1,3,5,7-tetramethylene-2,4,6,8-tetranitramine, Octogen), and mixtures thereof.
  • the explosive component may additionally or alternatively be selected from TATND (tetranitro-tetraminodecalin), HNS (hexanitrostilbene), TATB (triaminotrinitrobenzene), NTO (3-nitro-1,2,4-triazol-5-one), HNIW (2,4,6,8,10,12-hexanitrohexaazaisowurtzitane), GUDN (guanyldylurea dinitride), FOX-7 (1,1-diamino-2, 2-dinitroethene), and combinations thereof.
  • TATND tetranitro-tetraminodecalin
  • HNS hexanitrostilbene
  • TATB triaminotrinitrobenzene
  • NTO 3-nitro-1,2,4-triazol-5-one
  • HNIW 2,4,6,8,10,12-hexanitrohexaazaisowurtzitane
  • GUDN guanyldylurea dinitride
  • FOX-7
  • highly energetic materials may be used in place of or in addition to the compounds specified above.
  • suitable known highly energetic materials include picrite (nitroguanidine), aromatic nitramines such as tetryl, ethylene dinitramine, and nitrate esters such as nitroglycerine (glycerol trinitrate), butane triol trinitrate or pentaerythritol tetranitrate, DNAN (dinitroanisole), trinitrotoluene (TNT), inorganic oxidisers such as ammonium salts, for instance, ammonium nitrate, ammonium dinitramide (ADN) or ammonium perchlorate, and energetic alkali metal and alkaline earth metal salts.
  • picrite nitroguanidine
  • aromatic nitramines such as tetryl, ethylene dinitramine
  • nitrate esters such as nitroglycerine (glycerol trinitrate), butane triol trinitrate or
  • Polymer-bonded explosives include a polymeric binder which forms a matrix bonding explosive particles within.
  • the polymerisable binder thus may be selected from a wide range of polymers, depending upon the application in which the explosive will be used. However, in general at least a portion of the polymerisable binder will be selected, when cross linked to form polyurethanes, cellulosic materials such as cellulose acetate, polyesters, polybutadienes, polyethylenes, polyisobutylenes, PVA, chlorinated rubber, epoxy resins, two-pack polyurethane systems, alkyd/melanine, vinyl resins, alkyds, , thermoplastic elastomers such as butadiene-styrene block copolymers, and blends, copolymers and/or combinations thereof.
  • Energetic polymers may also be used either alone or in combination, these include polyNIMMO (poly(3-nitratomethyl-3-methyloxetane), polyGLYN (poly glycidyl nitrate) and GAP (glycidyl azide polymer). It is preferred that the polymerisable binder component be entirely selected from the list of polymerisable binders and/or energetic binders above either alone or in combination.
  • Polyurethanes are highly preferred polymerisable binders for PBX formation.
  • the polymerisable binder will comprise at least partly polyurethane, often the binder will comprise 50 - 100 wt% polyurethane, in some instances, 80 - 100 wt%.
  • the cross linking reagents may be selected from a variety of commonly known, cross linking reagents, the selection of which depends on the functionality of the polymerisable binders.
  • the highly preferred polyurethanes may typically be prepared by reacting polyol-terminated monomers or polymers with polyisocyanates.
  • a monomer or polymer diol may be cross linked with a cross linking reagent such as a diisocyanate.
  • the diisocyanate may be such as, for example, MDI (methylene diphenyl diisocyanate) and TDI (toluene diisocyanate) and IPDI (isophorone diisocyanate).
  • IPDI is generally preferred as it is a liquid and hence easy to dispense; it is relatively slow to react, providing a long pot-life and slower temperature changes during reaction; and it has a relatively low toxicity compared to most other isocyanates.
  • the polymerisable binder comprises polyurethane
  • the polyurethane polymerisable binder includes a hydroxyterminated polybutadiene.
  • the labile blocking group may be any reversible blocking group that may be furnished on the at least two reactive groups on the cross linking reagent, but which can be removed at a selected time by a stimulus, preferably an external stimulus.
  • the labile blocking group may be removed by a stimulus, such as, for example one or more of, heat, pressure, ultrasound, EM radiation, catalyst, or a shear force.
  • the labile blocking group is a thermally labile blocking group, one that ruptures when subjected to elevated temperatures.
  • the blocking group may comprise at least one nitro group, preferably at least two nitro groups or at least one sterically hindered branched chain hydrocarbyl group.
  • nitro, dinitro or trinitro groups on the aryl rings provides increased exothermic energy of the blocking group, and hence increased energy to the explosive composition.
  • the cross linking reagent is a diisocyanate group, with two blocking groups B, one on each isocyanate reactive group.
  • the labile blocking group B may comprise at least one nitro group, preferably at least two nitro groups or at least one sterically hindered branched chain hydrocarbyl group.
  • nitro, dinitro or trinitro groups such as for example on an aromatic ring, such as for example an aryl, phenyl or phenolic rings provides increased exothermic energy of the blocking group B, and hence increased energy to the explosive composition.
  • diisocyanate blocking group B is selected from B is
  • blocked diisocyanates may be selected to provide de-blocking temperatures in a range that occurs below the temperature of initiation of high explosive materials and above the temperatures that are generated during the mixing of the precure reagents. Thereby, there is a specific stimulus of heat which may be applied to the precure to cause the rupture of the microcapsule walls.
  • R 4 - R 8 may be selected from halo, nitro, lower chain C 1-6 alkyl
  • the substituted phenol comprises at least two nitro groups.
  • R 2 , R 3 , R 9 , and R 10 may be selected from, nitro, aryl, phenyl, lower chain C 1-6 alkyl, branched chain C 1-8 alkyl, preferably isopropyl or tert-butyl.
  • the thermal release of the blocking group may be in the range of from 50°C to 150°C, more preferably in the range of from 80°C to 120°C, such that the un-blocking occurs above current processing temperatures and well below the ignition temperature of the explosive.
  • a batch process for filling a munition with a cross linked polymer bonded explosive composition comprising the steps of:
  • reagents or further stimuli may be added to the composition to cause the curing reaction to commence, after the cross linking reagent has been de-blocked.
  • the curing reaction will commence directly as a result of causing the removal of the blocking group to furnish said reactive group on the cross linking reagent.
  • the step of causing the removal of the blocking group to furnish the cross linking reagent may be provided by applying at least one chemical stimulus and/or physical stimulus.
  • the stimulus may be one or more of heat, pressure ,ultrasound, EM radiation (e-beam, UV, IR), catalyst, shear force, preferably heat.
  • a cured explosive product comprising a polymer bonded explosive composition and a protonated blocking group; preferably the protonated blocking group comprises at least 1 nitro group, more preferably at least 2 nitro groups.
  • the explosive component of the polymer-bonded explosive may be in admixture with a metal powder which may function as a fuel or which may be included to achieve a specific terminal effect.
  • the metal powder may be selected from a wide range of metals including aluminium, magnesium, tungsten, alloys of these metals and combinations thereof. Often the fuel will be aluminium or an alloy thereof; often the fuel will be aluminium powder.
  • the polymer-bonded explosive comprises RDX.
  • the polymer-bonded explosive may comprise RDX as the only explosive component, or in combination with a secondary explosive component, such as HMX.
  • RDX comprises 50 - 100 wt% of the explosive component.
  • the polymerisable binder will be present in the range about 5 - 20 wt% of the polymer-bonded explosive, often about 5 - 15 wt%, or about 8 - 12 wt%.
  • the polymer-bonded explosive may comprise about 88 wt% RDX and about 12 wt% polyurethane binder.
  • the relative levels of RDX to polyurethane binder may be in the range about 75 - 95 wt% RDX and 5 - 25 wt% polyurethane binder.
  • Polymer-bonded explosives of this composition are commercially available, for example, Rowanex 1100TM.
  • the defoaming agent will be a polysiloxane.
  • the polysiloxane is selected from polyalkyl siloxanes, polyalkylaryl siloxanes, polyether siloxane co-polymers, and combinations thereof. It is often preferred that the polysiloxane be a polyalkylsiloxane; polydimethylsiloxane may typically be used.
  • the defoaming agent may be a combination of silicone-free surface active polymers, or a combination of these with a polysiloxane.
  • Such silicone-free polymers include alkoxylated alcohols, triisobutyl phosphate, and fumed silica.
  • Commercially available products which may be used include, BYK 088, BYK A500, BYK 066N and BYK A535 each available from BYK Additives and Instruments, a subdivision of Altana; TEGO MR2132 available from Evonik; and BASF SD23 and SD40, both available from BASF.
  • BYK A535 and TEGO MR2132 are often used as they are solventless products with good void reduction properties.
  • the defoaming agent is present in the range about 0.01 - 2 wt%, in some instances about 0.03 - 1.5 wt%, often about 0.05 - 1 wt%, in many cases about 0.25 or 0.5 - 1 wt%.
  • this i.e. below 0.01 wt%
  • the viscosity of the cast solution may be so low that the composition becomes non-homogenous as a result of sedimentation and segregation processes occurring within the mixture.
  • the explosive composition may include a solvent, any solvent in which at least one of the components is soluble and which does not adversely affect the safety of the final product may be used, as would be understood by the person skilled in the art. However, it is preferred, for the reasons described above, that in some embodiments that solvent be absent.
  • the solvent may be added as a carrier for the components of the composition.
  • the solvent will typically be removed from the explosive composition during the casting process, however some solvent residue may remain due to imperfections in the processing techniques or where it becomes uneconomical to remove the remaining solvent from the composition.
  • the solvent will be selected from diisobutylketone, polypropylene glycol, isoparaffins, propylene glycol, cyclohexanone, butyl glycol, ethylhexanol, white spirit, isoparaffins, xylene, methoxypropylacetate, butylacetate, naphthenes, glycolic acid butyl ester, alkyl benzenes and combinations thereof.
  • the solvent is selected from diisobutylketone, polypropylene glycol, isoparaffins, propylene glycol, isoparaffins, and combinations thereof.
  • the composition may also contain minor amounts of other additives commonly used in explosives compositions.
  • these include microcrystalline wax, energetic plasticisers, non-energetic plasticisers, antioxidants, catalysts, curing agents, metallic fuels, coupling agents, surfactants, dyes and combinations thereof.
  • Energetic plasticisers may be selected from eutectic mixtures of alkylnitrobenzenes (such as dinitro- and trinitro-ethyl benzene), alkyl derivatives of linear nitramines (such as an N-alkyl nitratoethyl-nitramine, for instance butyl-NENA), and glycidyl azide polymers.
  • Casting the explosive composition offers a greater flexibility of process design than can be obtained with pressing techniques. This is because the casting of different shapes can be facilitated through the simple substitution of one casting mould for another. In other words, the casting process is backwards-compatible with earlier processing apparatus. Conversely, where a change of product shape is required using pressing techniques, it is typically necessary to redesign a substantial portion of the production apparatus for compatibility with the mould, or the munition to be filled, leading to time and costs penalties. Further, casting techniques are less limited by size than pressing techniques which depend upon the transmission of pressure through the moulding powder to cause compaction. This pressure falls off rapidly with distance, making homogeneous charges with large length to diameter ratios (such as many shell fillings) more difficult to manufacture.
  • the casting process of the invention offers a moulded product (the cast explosive compositions described) with a reliably uniform fill regardless of the shape required by the casting. This may be partly attributed to the use of a delayed curing technique, Casting can occur in situ with the housing (such as a munition) to be filled acting as the mould; or the composition can be moulded and transferred into a housing in the munition in a separate step. Often casting will occur in situ.
  • compositions including polymer-bonded explosives and hydroxyterminated polybutadiene binders in particular are more elastomeric when cast than when pressed. This makes them less prone to undergoing a deflagration-to-detonation transition when exposed to accidental stimuli. Instead, such systems burn without detonating, making them safer to use than pressed systems.
  • the explosive component is desensitized with water prior to formation of the premix, a process known as wetting or phlegmatization.
  • a process known as wetting or phlegmatization it will typically be removed from the premix prior to further processing, for instance by heating during the mixing of the explosive component and the plasticiser.
  • the plasticiser will be absent; however the plasticiser will typically be present in the range 0 - 10 wt% of the plasticiser and explosive premix, often in the range 0.01 - 8 wt%, on occasion 0.5 - 7 wt% or 4 - 6 wt%.
  • the plasticiser will often be a non-energetic plasticiser, many are known in the art; however energetic plasticisers may also be used in some instances.
  • the cast explosive composition of the invention has utility both as a main charge or a booster charge in an explosive product. Often the composition will be the main charge.
  • the composition of the invention may be used in any "energetic" application such as, for example, uses include mortar bombs and artillery shells as discussed above. Additionally, the inventive composition may be used to prepare explosives for gun-launch applications, explosive filings for bombs and warheads, propellants, including composite propellants, base bleed compositions, gun propellants and gas generators.
  • the cast explosive composition may comprise, consist essentially of, or consist of any of the possible combinations of components described above and in the claims except for where otherwise specifically indicated.
  • Blocking group B and isophorone diisocyanate were dissolved in THF or CHCl 3 and refluxed until reaction has reached completion. The solvent was removed in vacuo to leave the blocked IPDI as a white solid. The yields are given in Table 1 below. Table 1. blocked di-isocyanates Compound Blocking group B Ratio of blocking group to IPDI Yield (%) 2.1 : 1 93 2.1 : 1 62 2 : 1 54 2 : 1 99 2 : 1 99 2 : 1 98 2 : 1 96 2 : 1 98 2 : 1 100 2 : 1 97
  • Blocked IPDI (8.68 wt %) was evenly dispersed in a composition of hydroxyl-terminated polybutadiene (91.1 wt %) and dibutyltin dilaurate (0.22 wt %) at 60 °C over a period of 2 hours.
  • the mixture was poured into a cast and cured between 90 - 120 °C over a period of several days to achieve a cross linked rubber. It was found for all examples there was no reaction between the blocked isocyanate and HTPB in the presence of the catalyst, at 55°C, even when left overnight.
  • the premix formulation 2 is a mixture of the explosive, HTBP polymerisable binder and other processing aids, and optionally a catalyst.
  • the premix formulation 2 is agitated such as by a stirrer 3.
  • a blocked cross linking reagent 4 (either as a solid or dissolved in a minimal aliquot of solvent), is added to the premix to form the precure formulation 5.
  • the blocked cross linking reagent 4 may be a diisocyanate such as IPDI.
  • the resultant precure admixture 5 is thoroughly mixed and is transferred to a munition 6 or mould (not shown) for later insertion into a munition.
  • the munition 6 when filled with the precure 5 may then be exposed to an external stimuli, such as heat, which removes the thermally labile blocking group on the blocked cross linking reagent 4, furnishing the cross linking reagent.
  • the cross linking reagent and HTPB polymerisable binder may then polymerise and form a polymer bonded explosive 7.
  • compositions of the invention are capable of being incorporated in the form of a variety of embodiments, only a few of which have been illustrated and described above.

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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)
  • Polyurethanes Or Polyureas (AREA)
EP15275169.9A 2015-07-07 2015-07-07 Composition pbx Ceased EP3115349A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP15275169.9A EP3115349A1 (fr) 2015-07-07 2015-07-07 Composition pbx
AU2016290783A AU2016290783B2 (en) 2015-07-07 2016-07-06 PBX composition
US15/746,980 US11186528B2 (en) 2015-07-07 2016-07-06 PBX composition
ES16741108T ES2913650T3 (es) 2015-07-07 2016-07-06 Composición de PBX
EP16741108.1A EP3319928B1 (fr) 2015-07-07 2016-07-06 Composition pbx
CA2991169A CA2991169C (fr) 2015-07-07 2016-07-06 Composition de pbx
PCT/GB2016/052028 WO2017006109A1 (fr) 2015-07-07 2016-07-06 Composition de pbx
US17/151,554 US11753353B2 (en) 2015-07-07 2021-01-18 PBX composition
US17/151,557 US11746069B2 (en) 2015-07-07 2021-01-18 PBX composition

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP15275169.9A EP3115349A1 (fr) 2015-07-07 2015-07-07 Composition pbx

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EP3115349A1 true EP3115349A1 (fr) 2017-01-11

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EP15275169.9A Ceased EP3115349A1 (fr) 2015-07-07 2015-07-07 Composition pbx

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2733712C1 (ru) * 2019-12-16 2020-10-06 Александр Александрович Кролевец Способ получения нанокапсул циклотриметилентринитроамина (гексогена)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3798090A (en) * 1968-12-04 1974-03-19 Hercules Inc Process for producing cross-linked propellants
US4263444A (en) * 1977-09-26 1981-04-21 Thiokol Corporation Hydroxy terminated polybutadiene based polyurethane bound propellant grains
US4803019A (en) * 1984-02-10 1989-02-07 Morton Thiokol, Inc. Process for forming a liner and cast propellant charge in a rocket motor casing
US5747603A (en) * 1987-05-19 1998-05-05 Thiokol Corporation Polymers used in elastomeric binders for high-energy compositions
US5942720A (en) * 1993-04-29 1999-08-24 Cordant Technologies Inc. Processing and curing aid for composite propellants

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3798090A (en) * 1968-12-04 1974-03-19 Hercules Inc Process for producing cross-linked propellants
US4263444A (en) * 1977-09-26 1981-04-21 Thiokol Corporation Hydroxy terminated polybutadiene based polyurethane bound propellant grains
US4803019A (en) * 1984-02-10 1989-02-07 Morton Thiokol, Inc. Process for forming a liner and cast propellant charge in a rocket motor casing
US5747603A (en) * 1987-05-19 1998-05-05 Thiokol Corporation Polymers used in elastomeric binders for high-energy compositions
US5942720A (en) * 1993-04-29 1999-08-24 Cordant Technologies Inc. Processing and curing aid for composite propellants

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DOUGLAS A WICKS ET AL: "Review Paper Blocked isocyanates III: Part A. Mechanisms and chemistry", 10 August 1999 (1999-08-10), pages 148 - 172, XP055178789, Retrieved from the Internet <URL:http://www.sciencedirect.com/science/article/pii/S0300944099000429/pdfft?md5=d4075654eff3162baf62e3276687f01c&pid=1-s2.0-S0300944099000429-main.pdf> [retrieved on 20150324] *
WICKS Z W: "BLOCKED ISOCYANATES", PROGRESS IN ORGANIC COATINGS, ELSEVIER BV, NL, vol. 3, 1 January 1975 (1975-01-01), pages 73 - 99, XP009072025, ISSN: 0300-9440, DOI: 10.1016/0300-9440(75)80002-6 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2733712C1 (ru) * 2019-12-16 2020-10-06 Александр Александрович Кролевец Способ получения нанокапсул циклотриметилентринитроамина (гексогена)

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