EP2318330B1 - Composition explosive à couler - Google Patents
Composition explosive à couler Download PDFInfo
- Publication number
- EP2318330B1 EP2318330B1 EP09785015.0A EP09785015A EP2318330B1 EP 2318330 B1 EP2318330 B1 EP 2318330B1 EP 09785015 A EP09785015 A EP 09785015A EP 2318330 B1 EP2318330 B1 EP 2318330B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- explosive
- defoaming agent
- composition
- cast
- explosive composition
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 127
- 239000002360 explosive Substances 0.000 title claims description 91
- 239000002518 antifoaming agent Substances 0.000 claims description 67
- 238000005266 casting Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 37
- 239000011230 binding agent Substances 0.000 claims description 27
- 229920001296 polysiloxane Polymers 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000004814 polyurethane Substances 0.000 claims description 13
- 229920002635 polyurethane Polymers 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- -1 polyethylenes Polymers 0.000 claims description 10
- 230000001603 reducing effect Effects 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims 2
- 239000004698 Polyethylene Substances 0.000 claims 1
- 229920002367 Polyisobutene Polymers 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 1
- 229920002301 cellulose acetate Polymers 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 229920002857 polybutadiene Polymers 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920000573 polyethylene Polymers 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920006132 styrene block copolymer Polymers 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 27
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 17
- 239000000654 additive Substances 0.000 description 17
- 239000004014 plasticizer Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000002156 mixing Methods 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
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- 239000005058 Isophorone diisocyanate Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
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- 230000000694 effects Effects 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 5
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000003380 propellant Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- HRKAMJBPFPHCSD-UHFFFAOYSA-N Tri-isobutylphosphate Chemical compound CC(C)COP(=O)(OCC(C)C)OCC(C)C HRKAMJBPFPHCSD-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
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- 239000011800 void material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 231100001261 hazardous Toxicity 0.000 description 3
- 231100000989 no adverse effect Toxicity 0.000 description 3
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000013530 defoamer Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- XOXVLXUOMLQTLM-UHFFFAOYSA-N 1-ethyl-2,3,4-trinitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1[N+]([O-])=O XOXVLXUOMLQTLM-UHFFFAOYSA-N 0.000 description 1
- PQSWCVYWEGIBPY-UHFFFAOYSA-N 2,2-dinitroethylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)CC1=CC=CC=C1 PQSWCVYWEGIBPY-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- JSOGDEOQBIUNTR-UHFFFAOYSA-N 2-(azidomethyl)oxirane Chemical compound [N-]=[N+]=NCC1CO1 JSOGDEOQBIUNTR-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- VFGRALUHHHDIQI-UHFFFAOYSA-N butyl 2-hydroxyacetate Chemical compound CCCCOC(=O)CO VFGRALUHHHDIQI-UHFFFAOYSA-N 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
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Classifications
-
- 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
-
- 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
- C06B21/00—Apparatus or methods for working-up explosives, e.g. forming, cutting, drying
-
- 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
- C06B23/009—Wetting agents, hydrophobing agents, dehydrating agents, antistatic additives, viscosity improvers, antiagglomerating agents, grinding agents and other additives for working up
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/10—Compositions containing a nitrated organic compound the compound being nitroglycerine
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B33/00—Compositions containing particulate metal, alloy, boron, silicon, selenium or tellurium with at least one oxygen supplying material which is either a metal oxide or a salt, organic or inorganic, capable of yielding a metal oxide
-
- 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
-
- 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 cast explosive compositions, their preparation and use.
- the invention relates to polymer-bonded explosive compositions.
- Explosives 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 a greater design flexibility than pressing.
- Polymer-bonded explosives are typically explosive powders bound into a polymer matrix.
- 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.
- US 6,893,516 describes an explosive mixture in which the crystalline explosive is coated with polysiloxanes to produce a granular product.
- the application of this coating to each crystal smoothes the surface of the crystals eliminating fine pores which could otherwise trigger unwanted reaction of the explosive.
- the polysiloxane coating reduces the sensitivity of the granular explosive, improving safety in handling and during any subsequent shaping steps.
- US 3 260 631 and US 3 245 849 disclose cured cast propellant compositions comprising 45-95 wt.% of an oxidizer such as ammonium nitrate or ammonium perchlorate, 5-55 wt.% of a binder, up to 0.01 wt.% of a silicone oil as a defoaming agent and up to 1 wt.% of a silicone free wetting agent as a processing aid for improving castability and processability.
- DE 14 46 902 discloses a cured cast propellant composition comprising ammonium perchlorate, an organic explosive, a binder and up to 0.01 wt.% of a silicone oil as a defoaming agent.
- the invention seeks to provide a cast explosive composition in which the stability of the composition is improved through the reduction of the number and/or total volume of voids. Such 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 cast explosive composition comprising a polymer-bonded explosive wherein the polymer-bonded explosive comprises in the range about 75 - 95 wt% RDX and in the range about 5 - 25 wt% polyurethane binder, and 0.05 - 2 wt% of a silicone free defoaming agent, wherein the defoaming agent is a combination of polymers.
- defoaming agent is intended to mean an additive with surface active properties which acts to eliminate voids from within the polymeric binder of the cast explosive composition. Any additive which does not perform this function is not regarded as constituting a defoaming agent within the meaning of the invention. In the art, such additives are also known as "anti-foaming agents", “deaerating agents” and “air release agents”.
- the voids are typically found within the body of the binder component of the polymer-bonded explosive, rather than at the interface between the binder and the explosive component. Removal of these voids is particularly desirable where the intended use of the explosive will result in exposure to high g-forces, such as would be the case in an artillery shell, mortar bomb or missile. It is believed that under such conditions, adiabatic compression of the voids occurs making the region around the void more prone to premature ignition. Another application where the removal of voids is of particular importance is where the intended use of the explosive will result in rapid deceleration on impact with a target but where penetration of the target is required before the munition is detonated. This would be the case with bombs and missiles. Where voids are present, adiabatic compression of these may result in ignition on impact, before penetration of the target has occurred.
- the defoaming agent reduces the viscosity of the composition, allowing the casting process to be carried out more rapidly than in the absence of this additive.
- compositions containing the defoaming agent have been seen in some instances to have a higher density in terms of %TMD achieved than when this additive is absent. This increase in density has also been linked to an improved stability and reduction in sensitivity of the explosive.
- the reduction of voids will correlate with an increase in density; however as the compositions of the invention are complex, an increase in density can only be taken as an indication that the number of voids has been reduced.
- other methods such as X-radiography are used to directly visualise the voids and to determine the effect of the defoaming agent.
- Another aspect not forming part of the invention relates to the use of a cast explosive composition as described herein in an explosive product, and a further aspect not forming part of the invention relates to an explosive product comprising a cast explosive composition as described herein.
- Polymer-bonded explosives include a polymeric binder which forms a matrix bonding explosive particles within.
- the binder will comprise at least partly polyurethane (5-25 wt.% of the composition), often the binder will comprise 50 - 100 wt% polyurethane, in some instances, 80 - 100 wt%.
- the binder will consist of polyurethane.
- Polyurethanes derived from MDI (methylene diphenyl diisocyanate) and TDI (toluene diisocyanate) and IPDI (isophorone diisocyanate) may be used.
- 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. It is also preferred that the polyurethane binder includes a hydroxyterminated polybutadiene.
- 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 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 is a combination of silicone-free surface active polymers.
- 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 may be added to the composition in a solvent carrier. However, it is generally preferred that solvents be absent. It has been found that the use of defoaming agents which are not carried in a solvent, or even the use of entirely solventless systems, is advantageous as there are fewer (or substantially no) volatile components present during processing of the composition, reducing the safety precautions and/or plant modifications needed. Further, the exclusion of solvents eliminates the risk of residual volatiles separating (for instance by evaporation or leaking) from the composition during storage resulting in unpredictable modifications of the properties of the compositions such as the creation of voids as a result of volatile evaporation.
- the defoaming agent is present in the range 0.05 - 2 wt%, in many cases about 0.25 or 0.5 - 1 wt%. At levels below this (i.e. below 0.01 wt%) there is often insufficient defoaming agent in the composition to significantly alter the properties of the polymer-bonded explosive, whereas above this level (i.e. above 2 wt%) the viscosity of the cast solution may be so low that the composition becomes inhomogeneous as a result of sedimentation and segregation processes occurring within the mixture.
- the defoaming agent not only acts to reduce viscosity, facilitating the casting process and the egress of voids from the composition during casting, but that the defoaming agents are surface active at the void-composition interfaces, causing the void bubbles to coalesce and hence be expelled from the composition as a result of the greater buoyancy of the larger bubbles produced. This results in compositions with fewer visible voids, which are more stable than known explosive compositions.
- 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 defoaming agent or another component 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. Accordingly, in some embodiments the polymer-bonded explosive and the defoaming agent are combined in the presence of a solvent.
- 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 inventive composition will be cast using "cast and curing" techniques. Accordingly, where the components of the cast explosive composition are not inherently curable (for instance, where all polymer components are thermoplastic polymers) a curative may optionally be present.
- the casting technique used is vacuum casting as the resulting product is generally of greater density and no visible voids compared with the equivalent air-cast product. In general, the curing step will take place after the casting step has occurred.
- 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 digomers.
- 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 casting technique, and partly to the presence of the defoaming agent.
- the defoaming agent substantially reduces the number of voids within the binder and hence the cast explosive composition. In some instances, the voids are substantially eliminated.
- 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 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 process of the invention may be a continuous or batch process as appropriate.
- Many known casting processes will be compatible for use with the invention as modification of these processes to allow for the addition of the defoaming agent to the polymer-bonded explosive and to allow the defoaming agent to perform its defoaming function during casting, is within the capabilities of the person skilled in the art.
- a continuous process this may make use of static mixing technology such as the technology described in EP 1485669 .
- a premix will typically be a mixture of an explosive component and a binder component, usually a plasticiser.
- the explosive component is desensitized with water prior to formation of the premix, a process known as wetting or phlegmatization.
- wetting or phlegmatization a process known as wetting or phlegmatization.
- retention of water within the premix is generally undesirable 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.
- a precure will typically be a combination of the premix and the other components of the composition with the exception of the catalyst and the curing agent. In some instances the defoaming agent will also be absent from the precure.
- 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 where the presence of voids causes safety or functional problems. Such 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.
- the process for reducing the voids in the composition may comprise, consist essentially of, or consist of the steps specified above and in the claims.
- compositions comprising silicone free combinations of polymers as defoaming agents constitute examples according to the present invention.
- TABLE 1 1. Defoaming Agent* Dosage (wt%) Viscosity (cps) # Density - Vacuum Cast (g/cm 3 ) Density - Air Cast (g/cm 3 ) % TMD ⁇ (air cast) No Additive - 0.12 1.608 1.608 99.3 Solution of foam-destroying polymers and polysiloxanes in isoparaffin solvent (BYK 088) @ 1.0 0.035 1.608 1.602 99.6 Solution of silicone-free foam-destroying polymers in Alkylbenzene/ methoxypropylacetate 12/1 (BYK A500) 1.0 0.033 1.612 1.606 99.9 Solution of foam-destroying polysiloxanes in diisobutylketone (BYK 066N) @ 0.1 0.12 1.614 1.619 99.6 Solution of foam-destroying polysilox
- the TMD is the sum of the relative volume of each component as determined from their relative mass within the composition and known density. As a result, the TMD gives a true indication of the density modification arising as a result of a change in the number of voids. @ No longer form part of the invention
- each of the defoaming agents at levels above 0.1 wt% reduces the viscosity of the composition making it easier to cast. Further, as the level of defoaming agent is increased to 1.0 wt%, the viscosity of the composition is further reduced.
- the presence of defoaming agent also increases the density, providing an indicator that the number of voids has been reduced.
- Calculation of the TMD provides a further indicator, as an increase in the TMD relative to that obtained where no additive is present shows that the number of voids in the sample has been reduced relative to the additive free composition.
- vacuum casting generally produces compositions of a higher relative density than air casting techniques where defoaming agents are present. Further, vacuum casting techniques generally have a more marked effect upon the density of compositions containing defoaming agents when compared to additive free or solvent only compositions.
- each defoaming agent is acting to reduce the number of voids in the compositions tested as each defoaming agent provides a composition which is either of higher density, or has a higher TMD, than the control compositions including either no additive, or solvent only.
- compositions comprising silicone free combinations of polymers as defoaming agents constitute examples according to the present invention.
- TABLE 2 1. Defoaming Agent Compatibility BYK 066N* @ Pass Solution of foam-destroying polysiloxanes in propylene glycol (BYK 088A) * @ Pass BYK 088* @ Pass BYK A500* Pass BYK A535* Pass TEGO MR2132 #@ Pass BASF SD23 ⁇ Pass BASF SD40 ⁇ Pass * Procured from BYK Additives and Instruments, a subdivision of Altana # Procured from Evonik ⁇ Procured from BASF @ no longer form part of the invention
- the test determines the 50% drop height for the test sample. This examines the whole probability of ignition versus stimulus-level relationship. Seven test heights equally spaced on a logarithmic scale are chosen and caps are tested to see if ignitions take place. Results are expressed in terms of Figures of Insensitiveness (F of I) relative to standard RDX. All tests are carried out on samples of ground up material. The Rotter Impact Test method was used to determine the F of I using an LSM Rotter machine.
- the F of I value for all of the Rowanex 1100/defoaming agent samples was found to be greater than or equal to the F of I value for Rowanex 1100 alone. This indicated that the presence of the defoaming agent has no adverse effect on the sensitivity of the PBX to mechanical impact and that as a result the combination products are no more hazardous, and in some cases less hazardous, to use than Rowanex 1100 alone. Without being bound by theory, this may be due to the marginal increase in binder, and resultant reduction in nitramine content because of the presence of the defoaming agent. It is further indicated that the Rowanex 1100/defoaming agent samples are likely to be no more sensitive to ignition than untreated Rowanex 1100.
- compositions including RDX were prepared, three of these compositions included defoaming agents.
- TABLE 4 Examples of Polymer-bonded Explosive (PBX) Compositions containing Defoaming Agents Abbreviation Full name Function PBX (wt%) PBX with 0.1% BYK-A500 Defoamer (wt %) PBX with 0.5% BYK-A535 Defoamer (wt%) PBX with 1%BYK-066N @ Defoamer (wt% DOA Dioctyl Adipate Plasticiser 7.00 6.99 6.96 6.93 HTPB Hydroxyterminated Polybutadiene Prepolymer 4.28 4.28 4.26 4.24 Lecithin Surfactant 0.30 0.30 0.30 0.30 AO2246 2,2'-methylenebis-(4-methyl-6-tertiary - butyl phenol) Antioxidant 0.10 0.10 0.10 0.10 0.10 IPDI Isophorone Diisocyanate Curing Agent 0.42
- compositions were prepared using cast and curing processes as described in Example 1 and no voids were detected. No adverse effect on chemical and mechanical properties was observed relative to the defoaming agent free RDX composition.
- a water-jacketed, vertical mixer fitted with a rotating stirrer blade was used for the preparation of the composition. All mixing was carried out under vacuum at a pressure of less than 10 mm Hg.
- the compositions of this example were prepared on a 5 Kg scale using the relative proportions of components set out in Example 4 above.
- the premix was prepared from RDX desensitised with water. The water was then driven off using techniques common in the art. The desensitised RDX (94 wt%) was then mixed with DOA plasticiser (6 wt%) to form the premix.
- the mixer was preheated to 60 ⁇ 2°C and the following ingredients weighed into the mixer in sequential order in relative amounts as described in Example 2 above:
- the composition was mixed for 15 minutes.
- the second, third and final quarter portions of premix were then added with 10 minutes of mixing between each addition and after the final addition.
- the mixer blades and bowl were scraped down to ensure that any unmixed material was transferred to the mixing zone of the bowl and the composition mixed for a further 60 minutes.
- Defoaming agent was then added and the composition mixed until the maximum reduction in viscosity upon addition of the defoaming agent to the composition was observed.
- mixing was for 25 minutes and viscosity reduction was measured using a torque meter fixed to the mixer, when the torque required to complete the mixing stabilised at a lower level than before the addition of the defoaming agent, the maximum reduction in viscosity is regarded as having been observed.
- the DBTL was added and the composition mixed for 15 minutes, then the IPDI added and the composition mixed for a further 15 minutes. After mixing the viscosity of the composition was recorded using a Brookfield viscometer (60°C).
- composition was cast and any excess mixture removed from the shell housings.
- the shells were placed onto a vibrating table and allowed to vibrate for 5 minutes.
- the charges were cured for 5 days at 65 ⁇ 2°C.
- PBX compositions of the invention such as the compositions of Example 4, from a precure.
- the techniques used would be well known to the person skilled in the art.
- Example 5 Mixing conditions were as for Example 5.
- the precure was prepared from the premix described in Example 5 above. To this premix was added all of the components of the composition of Example 5 except for the defoaming agent, catalyst and curing agent.
- the mixer was preheated to 60 ⁇ 2°C and the components of the precure added and heated for 15 minutes. The precure was then mixed for 30 minutes and the mixer blades and bowl scraped to ensure that any unmixed material was transferred to the mixing zone of the bowl. Defoaming agent was added and the composition mixed until the viscosity reducing effect of the defoaming agent is observed, this was measured as described in Example 5 and in this example required stirring for 25 minutes. The DBTL was added and the composition mixed for 15 minutes, then the IPDI added and the composition mixed for a further 15 minutes. The mixer blades and bowl were scraped to ensure that any unmixed material was transferred to the mixing zone of the bowl. After mixing the viscosity of the composition was recorded using a Brookfield viscometer (60°C).
- composition was cast and any excess mixture removed from the shell housings.
- the charges were cured for 5 days at 65 ⁇ 2°C.
- 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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Claims (10)
- Composition explosive coulée durcie comprenant un explosif lié par polymère qui comprend un liant et un explosif, dans laquelle l'explosif lié par polymère comprend dans la plage d'environ 75 à 95 % en poids de RDX et dans la plage d'environ 5 à 25 % en poids de liant de polyuréthane,
et 0,05 à 2 % en poids d'un agent antimousse sans silicone, l'agent antimousse étant une combinaison de polymères. - Composition explosive coulée selon la revendication 1 dans laquelle le liant est choisi parmi le polyuréthane, des matériaux cellulosiques tels que l'acétate de cellulose, des polyesters, des polybutadiènes, des polyéthylènes, des polyisobutylènes, le PVA, un caoutchouc chloré, des résines époxy, des systèmes de polyuréthane à deux composants, alkyde/mélanine, des résines vinyliques, des alkydes, des acrylates autoréticulés, des copolymères à blocs butadiène-styrène, polyNIMMO, polyGLYN, GAP, et des mélanges, des copolymères et/ou des combinaisons de ceux-ci.
- Composition explosive coulée selon l'une quelconque des revendications précédentes comprenant en outre une poudre métallique choisie parmi l'aluminium, le magnésium, le tungstène, des alliages de ces métaux et des combinaisons de ceux-ci en mélange avec l'explosif lié par polymère.
- Composition explosive coulée selon l'une quelconque des revendications précédentes, dans laquelle le liant est présent dans la plage de 5 % à 15 %.
- Composition explosive coulée selon la revendication 4, dans laquelle le liant est présent dans la plage de 8 % à 12 %.
- Composition explosive coulée selon l'une quelconque des revendications précédentes, dans laquelle l'agent antimousse est présent dans la plage de 0,5 à 1 % en poids.
- Procédé de réduction du nombre et/ou du volume total de vides dans une composition explosive coulée comprenant les étapes de :combinaison d'un explosif lié par polymère tel que défini dans les revendications 1 à 6, et de 0,05 à 2 % en poids d'un agent antimousse sans silicone, dans lequel l'agent antimousse est une combinaison de polymères ; etla coulée de la composition explosive.
- Procédé selon la revendication 7, dans lequel la composition explosive coulée est durcie.
- Procédé selon l'une quelconque des revendications 7 à 8, dans lequel la coulée comprend la coulée sous vide.
- Utilisation de 0,05 à 2 % en poids d'un agent antimousse sans silicone, dans laquelle l'agent antimousse est une combinaison de polymères pour réduire le nombre et/ou le volume total de vides dans une composition explosive coulée telle que définie dans l'une quelconque des revendications 1 à 6.
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GBGB0815936.0A GB0815936D0 (en) | 2008-08-29 | 2008-08-29 | Cast Explosive Composition |
PCT/GB2009/002081 WO2010023450A1 (fr) | 2008-08-29 | 2009-08-27 | Composition explosive à couler |
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EP2318330A1 EP2318330A1 (fr) | 2011-05-11 |
EP2318330B1 true EP2318330B1 (fr) | 2020-04-15 |
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EP09785015.0A Active EP2318330B1 (fr) | 2008-08-29 | 2009-08-27 | Composition explosive à couler |
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US (2) | US20110168306A1 (fr) |
EP (1) | EP2318330B1 (fr) |
JP (2) | JP2012500774A (fr) |
KR (2) | KR101731409B1 (fr) |
AU (1) | AU2009286497B2 (fr) |
CA (1) | CA2735320C (fr) |
GB (2) | GB0815936D0 (fr) |
WO (1) | WO2010023450A1 (fr) |
ZA (1) | ZA201101331B (fr) |
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US7964045B1 (en) * | 2003-06-11 | 2011-06-21 | The United States Of America As Represented By The Secretary Of The Army | Method for producing and using high explosive material |
DE10356437A1 (de) * | 2003-12-03 | 2005-07-07 | Clariant Gmbh | Entschäumer |
US8168016B1 (en) * | 2004-04-07 | 2012-05-01 | The United States Of America As Represented By The Secretary Of The Army | High-blast explosive compositions containing particulate metal |
JP4621474B2 (ja) * | 2004-10-19 | 2011-01-26 | 旭化成ケミカルズ株式会社 | 固体推進薬組成物 |
FR2893613B1 (fr) * | 2005-11-24 | 2008-04-04 | Eurenco France Sa | Procede bicomposant semi-continu perfectionne d'obtention d'un chargement explosif composite a matrice polyurethanne |
JPWO2007123120A1 (ja) * | 2006-04-19 | 2009-09-03 | 日本化薬株式会社 | 火薬組成物及び火薬組成物成形体、並びにそれらの製造方法 |
ATE504797T1 (de) * | 2007-12-18 | 2011-04-15 | Saab Ab | Verbessertes gehäuse für einen gefechtskopf |
US10329480B2 (en) * | 2013-07-05 | 2019-06-25 | National University Corporation Hokkaido University | Sheet integrated rare earth complex and use thereof |
-
2008
- 2008-08-29 GB GBGB0815936.0A patent/GB0815936D0/en not_active Ceased
-
2009
- 2009-08-27 GB GB1103090.5A patent/GB2475198B/en active Active
- 2009-08-27 EP EP09785015.0A patent/EP2318330B1/fr active Active
- 2009-08-27 KR KR1020157016085A patent/KR101731409B1/ko active IP Right Grant
- 2009-08-27 WO PCT/GB2009/002081 patent/WO2010023450A1/fr active Application Filing
- 2009-08-27 AU AU2009286497A patent/AU2009286497B2/en not_active Ceased
- 2009-08-27 KR KR1020117006550A patent/KR20110058826A/ko active Application Filing
- 2009-08-27 JP JP2011524450A patent/JP2012500774A/ja not_active Withdrawn
- 2009-08-27 CA CA2735320A patent/CA2735320C/fr not_active Expired - Fee Related
- 2009-08-27 US US13/061,308 patent/US20110168306A1/en not_active Abandoned
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2011
- 2011-02-18 ZA ZA2011/01331A patent/ZA201101331B/en unknown
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2015
- 2015-01-23 JP JP2015011407A patent/JP6169628B2/ja not_active Expired - Fee Related
-
2017
- 2017-11-29 US US15/825,783 patent/US20190023628A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
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None * |
Also Published As
Publication number | Publication date |
---|---|
JP2012500774A (ja) | 2012-01-12 |
GB201103090D0 (en) | 2011-04-06 |
EP2318330A1 (fr) | 2011-05-11 |
KR101731409B1 (ko) | 2017-04-28 |
GB2475198A (en) | 2011-05-11 |
JP2015145329A (ja) | 2015-08-13 |
AU2009286497A2 (en) | 2011-04-14 |
KR20110058826A (ko) | 2011-06-01 |
AU2009286497A1 (en) | 2010-03-04 |
US20190023628A1 (en) | 2019-01-24 |
KR20150085536A (ko) | 2015-07-23 |
US20110168306A1 (en) | 2011-07-14 |
GB2475198B (en) | 2013-05-29 |
WO2010023450A1 (fr) | 2010-03-04 |
AU2009286497B2 (en) | 2014-03-27 |
CA2735320A1 (fr) | 2010-03-04 |
CA2735320C (fr) | 2017-03-28 |
ZA201101331B (en) | 2012-04-25 |
JP6169628B2 (ja) | 2017-07-26 |
GB0815936D0 (en) | 2009-01-14 |
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