CA2301392C - Desensitisation of energetic materials - Google Patents
Desensitisation of energetic materials Download PDFInfo
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- CA2301392C CA2301392C CA2301392A CA2301392A CA2301392C CA 2301392 C CA2301392 C CA 2301392C CA 2301392 A CA2301392 A CA 2301392A CA 2301392 A CA2301392 A CA 2301392A CA 2301392 C CA2301392 C CA 2301392C
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- energetic
- plasticiser
- binder
- azide
- intermediate material
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- 239000000463 material Substances 0.000 title claims abstract description 86
- 238000000586 desensitisation Methods 0.000 title description 6
- 239000004014 plasticizer Substances 0.000 claims abstract description 66
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 239000002178 crystalline material Substances 0.000 claims abstract description 31
- 239000003380 propellant Substances 0.000 claims abstract description 30
- 239000011230 binding agent Substances 0.000 claims abstract description 25
- 150000001540 azides Chemical class 0.000 claims abstract description 15
- LSLGCKBDVWXMSH-UHFFFAOYSA-N 1-[1-(2,2-dinitropropoxy)ethoxy]-2,2-dinitropropane;1-(2,2-dinitropropoxymethoxy)-2,2-dinitropropane Chemical compound [O-][N+](=O)C([N+]([O-])=O)(C)COCOCC(C)([N+]([O-])=O)[N+]([O-])=O.[O-][N+](=O)C(C)([N+]([O-])=O)COC(C)OCC(C)([N+]([O-])=O)[N+]([O-])=O LSLGCKBDVWXMSH-UHFFFAOYSA-N 0.000 claims abstract description 9
- JSOGDEOQBIUNTR-UHFFFAOYSA-N 2-(azidomethyl)oxirane Chemical compound [N-]=[N+]=NCC1CO1 JSOGDEOQBIUNTR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 7
- QUAMCNNWODGSJA-UHFFFAOYSA-N 1,1-dinitrooxybutyl nitrate Chemical compound CCCC(O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QUAMCNNWODGSJA-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZQXWPHXDXHONFS-UHFFFAOYSA-N 1-(2,2-dinitropropoxymethoxy)-2,2-dinitropropane Chemical compound [O-][N+](=O)C([N+]([O-])=O)(C)COCOCC(C)([N+]([O-])=O)[N+]([O-])=O ZQXWPHXDXHONFS-UHFFFAOYSA-N 0.000 claims abstract description 5
- SIKUYNMGWKGHRS-UHFFFAOYSA-N 1-[1-(2,2-dinitropropoxy)ethoxy]-2,2-dinitropropane Chemical compound [O-][N+](=O)C(C)([N+]([O-])=O)COC(C)OCC(C)([N+]([O-])=O)[N+]([O-])=O SIKUYNMGWKGHRS-UHFFFAOYSA-N 0.000 claims abstract description 5
- FEKVXSGCKZHFCO-UHFFFAOYSA-N ethane nitric acid Chemical compound [N+](=O)(O)[O-].[N+](=O)(O)[O-].[N+](=O)(O)[O-].CC FEKVXSGCKZHFCO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000843 powder Substances 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- -1 poly(3-nitratomethyl-3-methyloxetane) Polymers 0.000 claims 1
- 239000002360 explosive Substances 0.000 abstract description 18
- 239000000945 filler Substances 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 5
- 238000010348 incorporation Methods 0.000 abstract description 5
- 238000000034 method Methods 0.000 description 15
- 238000002156 mixing Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 230000008569 process Effects 0.000 description 8
- UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 4
- GDDNTTHUKVNJRA-UHFFFAOYSA-N 3-bromo-3,3-difluoroprop-1-ene Chemical compound FC(F)(Br)C=C GDDNTTHUKVNJRA-UHFFFAOYSA-N 0.000 description 4
- 238000007580 dry-mixing Methods 0.000 description 4
- 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 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004200 deflagration Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000004449 solid propellant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 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
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical compound CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- 241001082241 Lythrum hyssopifolia Species 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- ADZAAKGRMMGJKM-UHFFFAOYSA-N oxiran-2-ylmethyl nitrate Chemical compound [O-][N+](=O)OCC1CO1 ADZAAKGRMMGJKM-UHFFFAOYSA-N 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000006163 transport media Substances 0.000 description 1
Classifications
-
- 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
- C06B45/18—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component
- C06B45/20—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an organic explosive or an organic thermic component
- C06B45/22—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an organic explosive or an organic thermic component the coating containing an organic compound
-
- 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
- C06B21/0008—Compounding the ingredient
- C06B21/0025—Compounding the ingredient the ingredient being a polymer bonded explosive or thermic component
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
- C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
- C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
- C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
- C06B45/105—The resin being a polymer bearing energetic groups or containing a soluble organic explosive
-
- 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
- C06B45/18—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component
- C06B45/20—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an organic explosive or an organic thermic component
- C06B45/22—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an organic explosive or an organic thermic component the coating containing an organic compound
- C06B45/24—Compositions or products which are defined by structure or arrangement of component of product comprising a coated component the component base containing an organic explosive or an organic thermic component the coating containing an organic compound the compound being an organic explosive or an organic thermic component
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Glass Compositions (AREA)
- Catalysts (AREA)
Abstract
An energetic material comprises an energetic crystalline material substantially coated in an energetic plasticiser material. Advantageously the energetic material comprises from 90 to 99% by weight of an energetic crystalline material and from 1 to 10% by weight of an energetic plasticiser material comprising a plasticiser selected from the group comprising Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP Azide), Bis(2,2-dinitropropyl)acetal / bis(2,2-dinitropropyl)formal (BDNPA/F) or mixtures of two or more of these plasticisers. The inventors have found that the combination of just a small quantity of energetic plasticiser material to the energetic crystalline material prior to incorporation into the bulk plasticiser, binder and filler mixture of an explosive or propellant composition has unexpected and advantageous effects.
Description
XA1011gb1 CA 02301392 2000-03-30 g u DESENSITISATION OF ENERGETIC MATERIALS
This invention relates to the desensitisation of energetic crystalline materials, in particular hexanitrohexaazaisowurtizane (HNIW) (also designated CI-20) but also other nitramine explosives such as cyclotrimethylene trinitramine (RDX) and cyclotetramethylene tetranitramine (HMX).
HNIW comprises a high density caged molecule recognised as a suitable energetic filler for propellant materials and explosives. Its use as a potential replacement for existing fillers such as RDX and HMX in cast double base, composite and novel propellants and other explosive materials has been postulated.
Propellant compositions used for launching relatively high mass projectiles are desirably highly energetic and energetically dense i.e. a small volume of the material will produce high potential kinetic energy via rapid gasification on ignition.
In general, such a propellant composition comprises three component materials;
an energetic filler, a plasticiser and a binder, the latter two components primarily provide the desirable mechanical properties of the resultant propellant material.
Choice of plasticiser and binder for a particular energetic filler will depend on a number of factors such as the projection range for the projectile, the extremes of temperature under which the end product is expected to operate and the chemical and physical interactions of the materials.
However, aside from the functional performance of the propellant material as an end product, industrial manufacturers of novel materials must consider the safety issues associated with the incorporation and manufacture of these filler, binder or plasticiser materials into rocketry. Thus, whilst from a performance point of view an energetic material may appear desirable for use as either a binder, plasticiser or XA1011gb1 CA 02301392 2000-03-30 filler in the predicted propellant formulation, the material must be safe for incorporation, processing and transportation. If an unsafe energetic material was to be incorporated into a propellant or explosive system, the unsafe material might initiate during either the manufacturing process or during transportation of the end product. This initiation might be via accidental friction or impact stimulation leading to deflagration or possibly a deflagration to detonation transition within the explosive material sufficient to cause an unwanted premature explosion. For this reason of safety, most known propellant materials (e.g. Ammonium Perchlorate /
hydroxy terminated polybutadiene based composite propellant) comprise, comparatively, energetically inert plasticiser and binder components.
In general, solid propellant materials such as those based on Ammonium Perchlorate, Hydroxy terminated polybutadiene (binder) and dioctyl sebacate (plasticiser) are manufactured by a dry mixing and blending process : this means that no additional desensitising solvent s (e.g. water) are added to this mix other than those that will be incorporated into the final propellant formulation.
This dry mix, once manufactured, is treated to facilitate curing of the binder material to provide the desirable mechanical properties for the propellant material. This method is generally considered preferable to a wet mixing process (where additional solvent is included as transport media or processing aid or as a desensitiser to improve safety) as it provides better homogeneity of mixing, and minimises delays in cleaning mixing equipment or drying out of the mixed end product prior to further processing (e.g. casting and curing).
Typically, existing propellant materials comprise around 6% by weight plasticiser to 85% by weight energetic filler. The propellant material will also generally comprise around 9% by total weight of binder and other filler materials.
This invention relates to the desensitisation of energetic crystalline materials, in particular hexanitrohexaazaisowurtizane (HNIW) (also designated CI-20) but also other nitramine explosives such as cyclotrimethylene trinitramine (RDX) and cyclotetramethylene tetranitramine (HMX).
HNIW comprises a high density caged molecule recognised as a suitable energetic filler for propellant materials and explosives. Its use as a potential replacement for existing fillers such as RDX and HMX in cast double base, composite and novel propellants and other explosive materials has been postulated.
Propellant compositions used for launching relatively high mass projectiles are desirably highly energetic and energetically dense i.e. a small volume of the material will produce high potential kinetic energy via rapid gasification on ignition.
In general, such a propellant composition comprises three component materials;
an energetic filler, a plasticiser and a binder, the latter two components primarily provide the desirable mechanical properties of the resultant propellant material.
Choice of plasticiser and binder for a particular energetic filler will depend on a number of factors such as the projection range for the projectile, the extremes of temperature under which the end product is expected to operate and the chemical and physical interactions of the materials.
However, aside from the functional performance of the propellant material as an end product, industrial manufacturers of novel materials must consider the safety issues associated with the incorporation and manufacture of these filler, binder or plasticiser materials into rocketry. Thus, whilst from a performance point of view an energetic material may appear desirable for use as either a binder, plasticiser or XA1011gb1 CA 02301392 2000-03-30 filler in the predicted propellant formulation, the material must be safe for incorporation, processing and transportation. If an unsafe energetic material was to be incorporated into a propellant or explosive system, the unsafe material might initiate during either the manufacturing process or during transportation of the end product. This initiation might be via accidental friction or impact stimulation leading to deflagration or possibly a deflagration to detonation transition within the explosive material sufficient to cause an unwanted premature explosion. For this reason of safety, most known propellant materials (e.g. Ammonium Perchlorate /
hydroxy terminated polybutadiene based composite propellant) comprise, comparatively, energetically inert plasticiser and binder components.
In general, solid propellant materials such as those based on Ammonium Perchlorate, Hydroxy terminated polybutadiene (binder) and dioctyl sebacate (plasticiser) are manufactured by a dry mixing and blending process : this means that no additional desensitising solvent s (e.g. water) are added to this mix other than those that will be incorporated into the final propellant formulation.
This dry mix, once manufactured, is treated to facilitate curing of the binder material to provide the desirable mechanical properties for the propellant material. This method is generally considered preferable to a wet mixing process (where additional solvent is included as transport media or processing aid or as a desensitiser to improve safety) as it provides better homogeneity of mixing, and minimises delays in cleaning mixing equipment or drying out of the mixed end product prior to further processing (e.g. casting and curing).
Typically, existing propellant materials comprise around 6% by weight plasticiser to 85% by weight energetic filler. The propellant material will also generally comprise around 9% by total weight of binder and other filler materials.
HNIW is a highly friction sensitive material having a rotary friction test Figure of Friction (F of F) of 0.7 and produces a highly ferocious response on reaction via friction stimuli. The exceptionally low F of F of HNIW
(when compared against other ingredients routinely used in propellant/explosive formulations) poses a considerable risk in the initial process of dry mixing the plasticiser, binder and filler, as is conventional in solid propellant manufacture. The low F of F value excludes the use of CL20 in large scale propellant manufacture in some explosive companies. Thus, the manufacturer is challenged with the task of providing a safe process by which HNIW can be incorporated into explosive and propellant materials whilst having minimal effect on the overall performance characteristics of the end product.
The invention relates to an intermediate material for a propellant composition, the intermediate material being in powder form and comprising from 90 to 99 weight percent of a particulate energetic crystalline material and from 1 to 10 weight percent of an energetic plasticiser material, the energetic plasticiser material substantially coating the individual particles of the energetic crystalline material.
In the first aspect, the invention is an energetic material comprising an energetic crystalline material substantially coated in an energetic plasticiser material.
Preferably the energetic crystalline material is particulate, the energetic plasticiser substantially coating individual particles of the energetic crystalline material.
The energetic material is advantageously in powder form, the powder comprising particles of energetic 3a crystalline material substantially coated in an energetic plasticiser material.
Advantageously the energetic material comprises from 90 to 99% by weight of an energetic crystalline material and from 1 to 10% by weight of an energetic plasticiser material.
The inventors have found that the combination of just a small quantity of energetic plasticiser material to the energetic crystalline material prior to incorporation into the bulk plasticiser, binder and filler mixture of an explosive or propellant XA1011gb1 CA 02301392 2000-03-30 composition has two unexpected and advantageous effects. Firstly, plasticiser addition leads to a reduction in the friction sensitivity of the energetic crystalline material to equivalent or less than that of many commonly used energetic filler materials such as ammonium perchlorate and secondly, the plasticiser addition also results in reduced ferocity of response on stimulation . The resultant novel intermediate of the energetic crystalline material and plasticiser can then be more safely used as a starting material for the dry mixing/blending/curing processes previously described used in the manufacture of known propellant and explosive compositions. These novel intermediate, plasticiser added, energetic crystalline material products are also more safely handled and transported than the pure energetic crystalline material.
In one particular method in accordance with the present invention, to manufacture an energetic material comprising an energetic crystalline material/energetic plasticiser mix, desirably the energetic crystalline material and energetic plasticiser material are mixed via a wet mixing process with the plasticiser material being added to, for example, water wet HNIW. The inherent characteristics of wet mixing reduces the friction arising within the mixture during the mixing process and thus minimises the risk of explosive reaction in the energetic crystalline material by friction stimuli. After mixing, the water wet, plasticised energetic crystalline material mix can be left to dry to a powdery state, the resultant dry powder formed being finely coated with the energetic plasticiser component. The resultant energetic crystalline material/energetic plasticiser mixture formed is a relatively friction insensitive energetic material when compared against pure, dry energetic crystalline material.
The inventors have found that the combination of just a small quantity of plasticiser material to an energetic crystalline material such as HNIW in manufacture of an explosive or propellant composition has an unexpected and advantageous effect XA1011gbl CA 02301392 2000-03-30 of reducing the friction sensitivity of HNIW to equivalent or less than that of commonly used energetic filler materials such as Ammonium perchlorate or HMX.
The resultant novel intermediate products manufactured by this desensitisation method can then be more safely used as a starting material for the dry mixing/blending/curing processes conventionally used in the manufacture of known propellant and explosive compositions. These novel intermediate products are also more safely handled and transported than the pure product. Another unexpected yet advantageous characteristic of these novel materials is that, once initiated, they display a reduced ferocity of response compared to that of the pure product.
The energetic plasticiser is preferably selected from the group comprising Butane Trios trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP
Azide), Bis(2,2-dinitropropyl)acetal / bis(2,2-dinitropropyl)formal (BDNPA/F) or mixtures of two or more of these plasticisers. As well as bringing about the desired desensitisation effect, these plasticisers add energy to the propellant system compared to the use of inert analogues. As a consequence, the intermediate material produced has a higher energy density compared to inert analogues :
this is a desirable characteristic of materials for use in rocketry / explosive programs as all constituents of the subsequent explosive / propellant formulation manufactured using the intermediate contribute energetically to the final formulation. The use of energetic crystalline materials desensitised with energetically inert plasticisers would have comparatively less energy than that of the proposed, energetic plasticisers formulations.
The energetic plasticiser material may comprise 100% of any of the plasticisers listed above, mixtures of those plasticisers listed above or optionally may be a blend of energetic plasticiser and a binder material (e.g. Poly(3-Nitratomethyl-3-...........................
XA1011gb1 CA 02301392 2000-03-30 Methyloxetane) (PolyNIMM ), Poly Glycidyl Nitrate (PoIyGLYN) or Glycidyl Azide Polymer (GAP)) of proportions encompassing from minimum quantity of 10% by weight plasticiser to 90% binder, to 100% plasticiser to 0% binder. The term "energetic plasticiser material" as referred to hereinafter should be construed accordingly with the above description.
Preferably, the novel energetic material will comprise between 1 % and 5% by weight of energetic plasticiser material and most preferably between 3% and 5%
by weight of energetic plasticiser material.
For mixed binder / plasticiser systems, preferably the energetic plasticiser material will comprise between 30% and 100% energetic plasticiser and 70% to 0% binder.
Most preferably the plasticiser content will be in the range 60% to 100%.
Thus the present invention provides a method for manufacture of a highly energetic, intermediate material based on a energetic crystalline material desensitised for safe incorporation into propellant or explosive formulations.
In a second aspect, the present invention provides a method for manufacture of a propellant material containing an energetic crystalline material comprising;
(i) mixing 1 to 10% by weight of an energetic plasticiser material with 99 to 90% by weight of the energetic crystalline material, (ii) mixing and/or blending the resultant product of step (i) with additional quantities of plasticiser and binder material as appropriate for the end application of the propellant material, (iii) curing the resultant product of step (ii).
XA1011gbl CA 02301392 2000-03-30 The energetic plasticiser material preferably contains a plasticiser selected from Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP
Azide), Bis(2,2 - dinitropropyl) acetal / bis (2,2 - dinitropropyl) formal (BDNPA/F) or mixtures of two or more of these plasticisers.
In a third aspect the invention is an explosive or propellant composition made from a an energetic material comprising;
(i) from 90 to 99% by weight HNIW; and (ii) from 1 to 10% by weight of an energetic plasticiser material comprising a plasticiser selected from the group comprising; Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP Azide), Bis(2,2-dinitropropyl)acetal / bis(2,2-dinitropropyl)formal (BDNPA/F), or mixtures of two or more of these components.
In order to more fully illustrate the novel methods, products and applications of this invention and their associated advantages, experimental data for some specific embodiments of the invention are now given by way of exemplification only. Although all analyses were carried out using Epsilon form HNIW, it is anticipated that this method of desensitisation would be effective on other crystal polymorphs of HNIW as well as known energetic crystalline materials such as cyclotrimethylene trinitramine (RDX) and cyclotetramethylene tetranitramine (HMX).
XA1011gbl CA 02301392 2000-03-30 1) Rotary friction testing of HNIW in the Epsilon crystal form was carried out and a Figure of Friction (FofF) = 0.7 was achieved. The sample response during testing was a violent report and flash.
2) 0.25g of TMETN stabilised with 1% 2-Nitrodiphenylamine (2NDPA) was added to 5g of dry Epsilon form HNIW and mixed. The material formed was a light orange powder. The material was assessed by rotary friction and the FofF achieved = 2.2. In addition to the reduction in friction sensitiveness, the violence of response was reduced from a violent report / flash for the pure HNIW material to a mild report without flash.
3) Replicate analysis of the formulation example given in example 2 were carried out with the substitution of TMETN with BTTN, a mixture of BTTN
and TMETN, DANPE, GAP Azide, BDNPA/F, PolyNIMMO, PoIyGLYN and GAP.
All materials appeared as white / yellow powders. For these mixtures, the friction sensitiveness determined were established as given in Table 1.
Table 1 Sample FofF
CL20 : TMETN 2.2 CL20 : BTTN 2.1 CL20 : BTTN / TMETN (50/50) 2.4 CL20 : GAP Azide 2.1 CL20 : DANPE 1.9 CL20 : PoIyGLYN 2.2 CL20: PolyNIMMO 1.9 CL20 : GAP 1.64) Replicate analysis of the formulation given in example 2 were carried out but with the substitution of TMETN with mixed binder : plasticiser formulations.
All mixtures formed white / light yellow powders. For these mixtures, the friction sensitiveness determined were established as shown in Table 2:
Table 2 Solid Binder Plasticiser FofF
CL20 PoIyGLYN GAP Azide 2.7 CL20 PoIyGLYN DANPE 2.5 CL20 PoIyGLYN BTTN / TMETN (80:20) 2.7 CL20 PoIyGLYN BDNPA/F 2.1 CL20 PolyNIMMO GAP Azide 2.9 CL20 PolyNIMMO DANPE 2.9 CL20 PolyNIMMO BTTN / TMETN (80:20) 3.1 CL20 PolyNIMMO BDNPA/F 2.4 CL20 GAP GAP Azide 2.8 CL20 GAP DANPE 2.7 CL20 GAP BTTN / TMETN (80:20) 2.8 CL20 GAP BDNPA/F 2.7 5) 40g of CL20 was wetted to 25% moisture content with deionised water and mixed thoroughly. 2g of TMETN (stabilised with 2% 2NDPA) was added and again mixed thoroughly. The final CL20 / water I TMETN / 2NDPA mixture was placed on the open bench to allow water evaporation and final water was removed under vacuum storage at 80 C for 2 hours). Friction sensitiveness assessment of the dry powder formed was carried out and an FofF = 2.4 determined.
(when compared against other ingredients routinely used in propellant/explosive formulations) poses a considerable risk in the initial process of dry mixing the plasticiser, binder and filler, as is conventional in solid propellant manufacture. The low F of F value excludes the use of CL20 in large scale propellant manufacture in some explosive companies. Thus, the manufacturer is challenged with the task of providing a safe process by which HNIW can be incorporated into explosive and propellant materials whilst having minimal effect on the overall performance characteristics of the end product.
The invention relates to an intermediate material for a propellant composition, the intermediate material being in powder form and comprising from 90 to 99 weight percent of a particulate energetic crystalline material and from 1 to 10 weight percent of an energetic plasticiser material, the energetic plasticiser material substantially coating the individual particles of the energetic crystalline material.
In the first aspect, the invention is an energetic material comprising an energetic crystalline material substantially coated in an energetic plasticiser material.
Preferably the energetic crystalline material is particulate, the energetic plasticiser substantially coating individual particles of the energetic crystalline material.
The energetic material is advantageously in powder form, the powder comprising particles of energetic 3a crystalline material substantially coated in an energetic plasticiser material.
Advantageously the energetic material comprises from 90 to 99% by weight of an energetic crystalline material and from 1 to 10% by weight of an energetic plasticiser material.
The inventors have found that the combination of just a small quantity of energetic plasticiser material to the energetic crystalline material prior to incorporation into the bulk plasticiser, binder and filler mixture of an explosive or propellant XA1011gb1 CA 02301392 2000-03-30 composition has two unexpected and advantageous effects. Firstly, plasticiser addition leads to a reduction in the friction sensitivity of the energetic crystalline material to equivalent or less than that of many commonly used energetic filler materials such as ammonium perchlorate and secondly, the plasticiser addition also results in reduced ferocity of response on stimulation . The resultant novel intermediate of the energetic crystalline material and plasticiser can then be more safely used as a starting material for the dry mixing/blending/curing processes previously described used in the manufacture of known propellant and explosive compositions. These novel intermediate, plasticiser added, energetic crystalline material products are also more safely handled and transported than the pure energetic crystalline material.
In one particular method in accordance with the present invention, to manufacture an energetic material comprising an energetic crystalline material/energetic plasticiser mix, desirably the energetic crystalline material and energetic plasticiser material are mixed via a wet mixing process with the plasticiser material being added to, for example, water wet HNIW. The inherent characteristics of wet mixing reduces the friction arising within the mixture during the mixing process and thus minimises the risk of explosive reaction in the energetic crystalline material by friction stimuli. After mixing, the water wet, plasticised energetic crystalline material mix can be left to dry to a powdery state, the resultant dry powder formed being finely coated with the energetic plasticiser component. The resultant energetic crystalline material/energetic plasticiser mixture formed is a relatively friction insensitive energetic material when compared against pure, dry energetic crystalline material.
The inventors have found that the combination of just a small quantity of plasticiser material to an energetic crystalline material such as HNIW in manufacture of an explosive or propellant composition has an unexpected and advantageous effect XA1011gbl CA 02301392 2000-03-30 of reducing the friction sensitivity of HNIW to equivalent or less than that of commonly used energetic filler materials such as Ammonium perchlorate or HMX.
The resultant novel intermediate products manufactured by this desensitisation method can then be more safely used as a starting material for the dry mixing/blending/curing processes conventionally used in the manufacture of known propellant and explosive compositions. These novel intermediate products are also more safely handled and transported than the pure product. Another unexpected yet advantageous characteristic of these novel materials is that, once initiated, they display a reduced ferocity of response compared to that of the pure product.
The energetic plasticiser is preferably selected from the group comprising Butane Trios trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP
Azide), Bis(2,2-dinitropropyl)acetal / bis(2,2-dinitropropyl)formal (BDNPA/F) or mixtures of two or more of these plasticisers. As well as bringing about the desired desensitisation effect, these plasticisers add energy to the propellant system compared to the use of inert analogues. As a consequence, the intermediate material produced has a higher energy density compared to inert analogues :
this is a desirable characteristic of materials for use in rocketry / explosive programs as all constituents of the subsequent explosive / propellant formulation manufactured using the intermediate contribute energetically to the final formulation. The use of energetic crystalline materials desensitised with energetically inert plasticisers would have comparatively less energy than that of the proposed, energetic plasticisers formulations.
The energetic plasticiser material may comprise 100% of any of the plasticisers listed above, mixtures of those plasticisers listed above or optionally may be a blend of energetic plasticiser and a binder material (e.g. Poly(3-Nitratomethyl-3-...........................
XA1011gb1 CA 02301392 2000-03-30 Methyloxetane) (PolyNIMM ), Poly Glycidyl Nitrate (PoIyGLYN) or Glycidyl Azide Polymer (GAP)) of proportions encompassing from minimum quantity of 10% by weight plasticiser to 90% binder, to 100% plasticiser to 0% binder. The term "energetic plasticiser material" as referred to hereinafter should be construed accordingly with the above description.
Preferably, the novel energetic material will comprise between 1 % and 5% by weight of energetic plasticiser material and most preferably between 3% and 5%
by weight of energetic plasticiser material.
For mixed binder / plasticiser systems, preferably the energetic plasticiser material will comprise between 30% and 100% energetic plasticiser and 70% to 0% binder.
Most preferably the plasticiser content will be in the range 60% to 100%.
Thus the present invention provides a method for manufacture of a highly energetic, intermediate material based on a energetic crystalline material desensitised for safe incorporation into propellant or explosive formulations.
In a second aspect, the present invention provides a method for manufacture of a propellant material containing an energetic crystalline material comprising;
(i) mixing 1 to 10% by weight of an energetic plasticiser material with 99 to 90% by weight of the energetic crystalline material, (ii) mixing and/or blending the resultant product of step (i) with additional quantities of plasticiser and binder material as appropriate for the end application of the propellant material, (iii) curing the resultant product of step (ii).
XA1011gbl CA 02301392 2000-03-30 The energetic plasticiser material preferably contains a plasticiser selected from Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP
Azide), Bis(2,2 - dinitropropyl) acetal / bis (2,2 - dinitropropyl) formal (BDNPA/F) or mixtures of two or more of these plasticisers.
In a third aspect the invention is an explosive or propellant composition made from a an energetic material comprising;
(i) from 90 to 99% by weight HNIW; and (ii) from 1 to 10% by weight of an energetic plasticiser material comprising a plasticiser selected from the group comprising; Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP Azide), Bis(2,2-dinitropropyl)acetal / bis(2,2-dinitropropyl)formal (BDNPA/F), or mixtures of two or more of these components.
In order to more fully illustrate the novel methods, products and applications of this invention and their associated advantages, experimental data for some specific embodiments of the invention are now given by way of exemplification only. Although all analyses were carried out using Epsilon form HNIW, it is anticipated that this method of desensitisation would be effective on other crystal polymorphs of HNIW as well as known energetic crystalline materials such as cyclotrimethylene trinitramine (RDX) and cyclotetramethylene tetranitramine (HMX).
XA1011gbl CA 02301392 2000-03-30 1) Rotary friction testing of HNIW in the Epsilon crystal form was carried out and a Figure of Friction (FofF) = 0.7 was achieved. The sample response during testing was a violent report and flash.
2) 0.25g of TMETN stabilised with 1% 2-Nitrodiphenylamine (2NDPA) was added to 5g of dry Epsilon form HNIW and mixed. The material formed was a light orange powder. The material was assessed by rotary friction and the FofF achieved = 2.2. In addition to the reduction in friction sensitiveness, the violence of response was reduced from a violent report / flash for the pure HNIW material to a mild report without flash.
3) Replicate analysis of the formulation example given in example 2 were carried out with the substitution of TMETN with BTTN, a mixture of BTTN
and TMETN, DANPE, GAP Azide, BDNPA/F, PolyNIMMO, PoIyGLYN and GAP.
All materials appeared as white / yellow powders. For these mixtures, the friction sensitiveness determined were established as given in Table 1.
Table 1 Sample FofF
CL20 : TMETN 2.2 CL20 : BTTN 2.1 CL20 : BTTN / TMETN (50/50) 2.4 CL20 : GAP Azide 2.1 CL20 : DANPE 1.9 CL20 : PoIyGLYN 2.2 CL20: PolyNIMMO 1.9 CL20 : GAP 1.64) Replicate analysis of the formulation given in example 2 were carried out but with the substitution of TMETN with mixed binder : plasticiser formulations.
All mixtures formed white / light yellow powders. For these mixtures, the friction sensitiveness determined were established as shown in Table 2:
Table 2 Solid Binder Plasticiser FofF
CL20 PoIyGLYN GAP Azide 2.7 CL20 PoIyGLYN DANPE 2.5 CL20 PoIyGLYN BTTN / TMETN (80:20) 2.7 CL20 PoIyGLYN BDNPA/F 2.1 CL20 PolyNIMMO GAP Azide 2.9 CL20 PolyNIMMO DANPE 2.9 CL20 PolyNIMMO BTTN / TMETN (80:20) 3.1 CL20 PolyNIMMO BDNPA/F 2.4 CL20 GAP GAP Azide 2.8 CL20 GAP DANPE 2.7 CL20 GAP BTTN / TMETN (80:20) 2.8 CL20 GAP BDNPA/F 2.7 5) 40g of CL20 was wetted to 25% moisture content with deionised water and mixed thoroughly. 2g of TMETN (stabilised with 2% 2NDPA) was added and again mixed thoroughly. The final CL20 / water I TMETN / 2NDPA mixture was placed on the open bench to allow water evaporation and final water was removed under vacuum storage at 80 C for 2 hours). Friction sensitiveness assessment of the dry powder formed was carried out and an FofF = 2.4 determined.
Claims (9)
1. An intermediate material for a propellant composition, the intermediate material being in powder form and comprising from 90 to 99 weight percent of a particulate energetic crystalline material and from 1 to 10 weight percent of an energetic plasticiser material, the energetic plasticiser material substantially coating the individual particles of the energetic crystalline material.
2. An intermediate material as claimed in claim 1, wherein the amount of energetic plasticiser material is between 1 and 5 weight percent.
3. An intermediate material as claimed in claim 2, wherein the amount of energetic plasticiser material is between 3 and 5 weight percent.
4. An intermediate material as claimed in any one of claims 1 to 3, wherein the energetic plasticiser material is Butane Triol trinitrate (BTTN), Trimethylanol ethane trinitrate (TMETN), Diazidonitrazapentane (DANPE), Glycidyl Azide Polymer (Azide Derivative) (GAP Azide), Bis(2,2-dinitropropyl)acetal/ bis(2,2-dinitropropyl)formal (BDNPA/F), or a mixture thereof.
5. An intermediate material as claimed in any one of claims 1 to 4, wherein the energetic crystalline material is hexanitrohexaazaisowurtizane.
6. An intermediate material as claimed in any one of claims 1 to 5, which also comprises a binder.
7. An intermediate material as claimed in claim 6, wherein the proportion of energetic plasticiser material and binder by weight is from 10% to 100% energetic plasticiser and 90% to 0% binder.
8. An intermediate material as claimed in claim 6 or 7, wherein the binder is an energetic binder.
9. An intermediate material as claimed in claim 6 or 7, wherein the binder is poly(3-nitratomethyl-3-methyloxetane) (PolyNIMMO), polyglycidyl nitrate (PolyGLYN), or glycidyl azide polymer (GAP).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9913262.3A GB9913262D0 (en) | 1999-06-09 | 1999-06-09 | Desensitation of energetic materials |
| GB9913262.3 | 1999-06-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2301392A1 CA2301392A1 (en) | 2004-01-28 |
| CA2301392C true CA2301392C (en) | 2010-10-12 |
Family
ID=10854917
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2301392A Expired - Lifetime CA2301392C (en) | 1999-06-09 | 2000-03-30 | Desensitisation of energetic materials |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US20040221934A1 (en) |
| CA (1) | CA2301392C (en) |
| DE (1) | DE10027413B4 (en) |
| ES (1) | ES2190838B2 (en) |
| FR (1) | FR2840604B1 (en) |
| GB (2) | GB9913262D0 (en) |
| IT (1) | ITRM20000309A1 (en) |
| NL (1) | NL1015399C2 (en) |
| SE (1) | SE524594C2 (en) |
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| FR2925488B1 (en) * | 2007-12-19 | 2011-12-23 | Snpe Materiaux Energetiques | CRYSTAL COATING DENSIBILIZATION OF EXPLOSIVE ENERGY SUBSTANCES; CRYSTALS SUCH AS COATED SUBSTANCES, ENERGY MATERIALS. |
| CN103044173B (en) * | 2012-12-06 | 2015-03-04 | 中国工程物理研究院化工材料研究所 | Method for preparing ordered porous energetic crystal material |
| CN103396274B (en) * | 2013-08-16 | 2015-08-05 | 中国工程物理研究院化工材料研究所 | The preparation method of Hexanitrohexaazaisowurtzitane and m-dinitrobenzene eutectic explosive |
| RU2670111C1 (en) * | 2018-01-25 | 2018-10-18 | Амир Рахимович Арисметов | Method of increasing temperature stability of explosive substances |
| RU2703204C1 (en) * | 2018-06-27 | 2019-10-15 | Акционерное общество "Взрывгеосервис" | Explosive composition |
| CN114539012A (en) * | 2020-11-25 | 2022-05-27 | 北京理工大学 | Composite energetic plasticizer suitable for GAP-based casting explosive and propellant and preparation method and application thereof |
| CN113416308B (en) * | 2021-07-08 | 2022-02-01 | 北京理工大学 | Porous aromatic skeleton EPAF-2 material, CL-20@ EPAF-2 composite energetic material and preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932050A (en) * | 1933-10-24 | Explosive coating material | ||
| US2615800A (en) * | 1948-04-27 | 1952-10-28 | Commercial Solvents Corp | Coated granular explosive composition |
| US3151164A (en) * | 1960-01-25 | 1964-09-29 | Phillips Petroleum Co | Nitraza thia polymer compositions |
| US3461007A (en) * | 1968-04-29 | 1969-08-12 | Commercial Solvents Corp | Reducing sensitivity of primary explosives to initiation by electrostatic discharges |
| US3984264A (en) * | 1969-04-01 | 1976-10-05 | The United States Of America As Represented By The Secretary Of The Army | Siloxane coatings for solid propellant ingredients |
| US4163681A (en) * | 1970-04-15 | 1979-08-07 | The United States Of America As Represented By The Secretary Of The Navy | Desensitized explosives and castable thermally stable high energy explosive compositions therefrom |
| FR2501194A1 (en) * | 1971-08-04 | 1982-09-10 | Aerojet General Co | Solid explosive desensitised with phlegmatising agent - contg. functional gps. which are reactive to binder ingredients |
| US3778319A (en) * | 1973-01-30 | 1973-12-11 | Atomic Energy Commission | High-energy plastic-bonded explosive |
| NZ187824A (en) * | 1977-08-01 | 1980-08-26 | Ici Australia Ltd | Fusecord wherein outer thermoplastic sheath enclosed by flexible strands adhered to sheath by adhesive from a water-bearing adhesive composition |
| US4168191A (en) * | 1978-06-29 | 1979-09-18 | The United States Of America As Represented By The United States Department Of Energy | Thermally stable, plastic-bonded explosives |
| DE3010052C2 (en) * | 1980-03-15 | 1982-09-09 | Friedrich-Ulf 8899 Rettenbach Deisenroth | Process for the production of plastic-bound explosives |
| FR2545478B1 (en) * | 1983-05-03 | 1985-07-05 | Commissariat Energie Atomique | COLD-MOLDABLE EXPLOSIVE COMPOSITION AND PROCESS FOR PREPARING THE SAME |
| US5049213A (en) * | 1985-10-10 | 1991-09-17 | The United States Of America As Represented By The Secretary Of The Navy | Plastic bonded explosives using fluorocarbon binders |
| US4842659A (en) * | 1988-04-22 | 1989-06-27 | The United States Of America As Represented By The Secretary Of The Army | Insensitive high energy explosive compositions |
| DE3934368C1 (en) * | 1989-10-14 | 1990-11-15 | Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung Ev, 8000 Muenchen, De | |
| US5547526A (en) * | 1990-03-06 | 1996-08-20 | Daimler-Benz Aerospace Ag | Pressable explosive granular product and pressed explosive charge |
| DE4233629C2 (en) * | 1992-10-06 | 1994-09-15 | Wasagchemie Sythen Gmbh | Process for producing a powder precursor and powder precursor |
| US5567912A (en) * | 1992-12-01 | 1996-10-22 | The United States Of America As Represented By The Secretary Of The Army | Insensitive energetic compositions, and related articles and systems and processes |
| US5487851A (en) * | 1993-12-20 | 1996-01-30 | Thiokol Corporation | Composite gun propellant processing technique |
| US5587553A (en) * | 1994-11-07 | 1996-12-24 | Thiokol Corporation | High performance pressable explosive compositions |
| US5759458A (en) * | 1996-07-26 | 1998-06-02 | Thiokol Corporation | Process for the manufacture of high performance gun propellants |
| US5750921A (en) * | 1997-07-07 | 1998-05-12 | Chan; May L. | Waste-free method of making molding powder |
| US6214137B1 (en) * | 1997-10-07 | 2001-04-10 | Cordant Technologies Inc. | High performance explosive containing CL-20 |
| US6217799B1 (en) * | 1997-10-07 | 2001-04-17 | Cordant Technologies Inc. | Method for making high performance explosive formulations containing CL-20 |
| DE19907809C2 (en) * | 1999-02-24 | 2002-10-10 | Nitrochemie Gmbh | Process for the production of one-, two- or three-base propellant charge powders for gun ammunition |
-
1999
- 1999-06-09 GB GBGB9913262.3A patent/GB9913262D0/en not_active Ceased
-
2000
- 2000-03-30 CA CA2301392A patent/CA2301392C/en not_active Expired - Lifetime
- 2000-04-04 ES ES200000843A patent/ES2190838B2/en not_active Expired - Fee Related
- 2000-04-27 FR FR0005389A patent/FR2840604B1/en not_active Expired - Lifetime
- 2000-05-18 GB GB0011861A patent/GB2374867B/en not_active Expired - Lifetime
- 2000-05-30 DE DE10027413.7A patent/DE10027413B4/en not_active Expired - Lifetime
- 2000-06-06 IT IT000309A patent/ITRM20000309A1/en unknown
- 2000-06-08 NL NL1015399A patent/NL1015399C2/en not_active IP Right Cessation
- 2000-06-08 SE SE0002149A patent/SE524594C2/en not_active IP Right Cessation
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2002
- 2002-02-21 US US10/093,885 patent/US20040221934A1/en not_active Abandoned
-
2010
- 2010-09-20 US US12/923,411 patent/US20110108171A1/en not_active Abandoned
-
2014
- 2014-03-05 US US14/197,543 patent/US20140261928A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| NL1015399C2 (en) | 2003-08-19 |
| ES2190838B2 (en) | 2005-06-16 |
| GB9913262D0 (en) | 2002-08-21 |
| GB2374867B (en) | 2003-12-10 |
| NL1015399A1 (en) | 2003-03-13 |
| US20110108171A1 (en) | 2011-05-12 |
| SE524594C2 (en) | 2004-08-31 |
| US20140261928A1 (en) | 2014-09-18 |
| SE0002149L (en) | 2003-06-13 |
| GB2374867A (en) | 2002-10-30 |
| ES2190838A1 (en) | 2003-08-16 |
| FR2840604A1 (en) | 2003-12-12 |
| DE10027413B4 (en) | 2014-11-06 |
| GB0011861D0 (en) | 2002-08-21 |
| CA2301392A1 (en) | 2004-01-28 |
| FR2840604B1 (en) | 2006-03-17 |
| US20040221934A1 (en) | 2004-11-11 |
| ITRM20000309A1 (en) | 2001-12-06 |
| DE10027413A1 (en) | 2003-08-07 |
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