CA1325518C - Energetic materials containing heteroalicyclic nitramine compound - Google Patents

Energetic materials containing heteroalicyclic nitramine compound

Info

Publication number: CA1325518C
Authority: CA; Canada
Prior art keywords: component; weight; composition; compound; nitro
Prior art date: 1986-07-04
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.): Expired - Fee Related

Application number

CA000541310A

Other languages

English (en)

French (fr)

Inventor

Ronald Benjamin Holt

John Charles Martin Phillips

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BAE Systems PLC

Original Assignee

Royal Ordnance PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-07-04

Filing date

1987-07-03

Publication date

1993-12-28

1986-07-04 Priority claimed from GB868616322A external-priority patent/GB8616322D0/en

1987-07-03 Application filed by Royal Ordnance PLC filed Critical Royal Ordnance PLC

1993-12-28 Application granted granted Critical

1993-12-28 Publication of CA1325518C publication Critical patent/CA1325518C/en

2010-12-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 nitramine compound Chemical class 0.000 title claims abstract description 13
BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 title claims abstract description 7
POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 title claims abstract description 7
239000000463 material Substances 0.000 title description 20
239000000203 mixture Substances 0.000 claims abstract description 98
150000001875 compounds Chemical class 0.000 claims abstract description 29
239000011230 binding agent Substances 0.000 claims abstract description 14
239000004014 plasticizer Substances 0.000 claims abstract description 13
239000000945 filler Substances 0.000 claims abstract description 6
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 claims description 26
239000003380 propellant Substances 0.000 claims description 25
239000000020 Nitrocellulose Substances 0.000 claims description 24
229920001220 nitrocellulos Polymers 0.000 claims description 24
PZIMIYVOZBTARW-UHFFFAOYSA-N centralite Chemical compound C=1C=CC=CC=1N(CC)C(=O)N(CC)C1=CC=CC=C1 PZIMIYVOZBTARW-UHFFFAOYSA-N 0.000 claims description 13
229920006217 cellulose acetate butyrate Polymers 0.000 claims description 12
150000002828 nitro derivatives Chemical class 0.000 claims description 10
RMBFBMJGBANMMK-UHFFFAOYSA-N 2,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RMBFBMJGBANMMK-UHFFFAOYSA-N 0.000 claims description 7
POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical class O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 claims description 6
PQSWCVYWEGIBPY-UHFFFAOYSA-N 2,2-dinitroethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)CC1=CC=CC=C1 PQSWCVYWEGIBPY-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
150000004996 alkyl benzenes Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
239000000028 HMX Substances 0.000 claims description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
150000005224 alkoxybenzenes Chemical class 0.000 claims description 4
OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
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 claims description 4
XUUSVHGZGPBZLS-UHFFFAOYSA-N 1,3-dimethyl-2,4-dinitrobenzene Chemical group CC1=CC=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O XUUSVHGZGPBZLS-UHFFFAOYSA-N 0.000 claims description 3
ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
GHLOZOFSZVNFMD-UHFFFAOYSA-N 3,3-dinitropropylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)CCC1=CC=CC=C1 GHLOZOFSZVNFMD-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
229920002678 cellulose Polymers 0.000 claims description 2
VMMLSJNPNVTYMN-UHFFFAOYSA-N dinitromethylbenzene Chemical class [O-][N+](=O)C([N+]([O-])=O)C1=CC=CC=C1 VMMLSJNPNVTYMN-UHFFFAOYSA-N 0.000 claims description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000005186 trinitrobenzenes Chemical class 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims 2
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims 1
UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 8
239000004615 ingredient Substances 0.000 description 6
SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 5
239000000654 additive Substances 0.000 description 5
238000001125 extrusion Methods 0.000 description 5
IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 4
229920002301 cellulose acetate Polymers 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000002904 solvent Substances 0.000 description 4
XTRDKALNCIHHNI-UHFFFAOYSA-N 2,6-dinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O XTRDKALNCIHHNI-UHFFFAOYSA-N 0.000 description 3
VDKWJWFQFPWXFC-UHFFFAOYSA-N 2-ethyl-1,3,5-trinitrobenzene Chemical compound CCC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O VDKWJWFQFPWXFC-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229960003711 glyceryl trinitrate Drugs 0.000 description 3
238000000034 method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
239000002360 explosive Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
PNBOBRKDXRJMTL-UHFFFAOYSA-N (2-nitrophenyl) benzoate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 PNBOBRKDXRJMTL-UHFFFAOYSA-N 0.000 description 1
JWLQSDXEKWFFBU-UHFFFAOYSA-N (3-nitrophenyl) benzoate Chemical compound [O-][N+](=O)C1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 JWLQSDXEKWFFBU-UHFFFAOYSA-N 0.000 description 1
GMKZBFFLCONHDE-UHFFFAOYSA-N (4-nitrophenyl) benzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C1=CC=CC=C1 GMKZBFFLCONHDE-UHFFFAOYSA-N 0.000 description 1
RDLIBIDNLZPAQD-UHFFFAOYSA-N 1,2,4-butanetriol trinitrate Chemical compound [O-][N+](=O)OCCC(O[N+]([O-])=O)CO[N+]([O-])=O RDLIBIDNLZPAQD-UHFFFAOYSA-N 0.000 description 1
OJJRABFYHOHGGU-UHFFFAOYSA-N 1,2,4-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 OJJRABFYHOHGGU-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
DWVNLBRNGAANPI-UHFFFAOYSA-N 1,2-dimethoxy-3-nitrobenzene Chemical compound COC1=CC=CC([N+]([O-])=O)=C1OC DWVNLBRNGAANPI-UHFFFAOYSA-N 0.000 description 1
YFWBUVZWCBFSQN-UHFFFAOYSA-N 1,2-dimethoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C=C1OC YFWBUVZWCBFSQN-UHFFFAOYSA-N 0.000 description 1
FVHAWXWFPBPFOS-UHFFFAOYSA-N 1,2-dimethyl-3-nitrobenzene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C FVHAWXWFPBPFOS-UHFFFAOYSA-N 0.000 description 1
HFZKOYWDLDYELC-UHFFFAOYSA-N 1,2-dimethyl-4-nitrobenzene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C HFZKOYWDLDYELC-UHFFFAOYSA-N 0.000 description 1
OFMLQCPPVSVIDD-UHFFFAOYSA-N 1,3,5-trimethyl-2,4-dinitrobenzene Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(C)=C1[N+]([O-])=O OFMLQCPPVSVIDD-UHFFFAOYSA-N 0.000 description 1
SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 description 1
YSIBQULRFXITSW-OWOJBTEDSA-N 1,3,5-trinitro-2-[(e)-2-(2,4,6-trinitrophenyl)ethenyl]benzene Chemical group [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1\C=C\C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O YSIBQULRFXITSW-OWOJBTEDSA-N 0.000 description 1
MVBXGGHFJZBKFJ-UHFFFAOYSA-N 1,3-dimethoxy-2-nitrobenzene Chemical compound COC1=CC=CC(OC)=C1[N+]([O-])=O MVBXGGHFJZBKFJ-UHFFFAOYSA-N 0.000 description 1
HDFQKJQEWGVKCQ-UHFFFAOYSA-N 1,3-dimethyl-2-nitrobenzene Chemical compound CC1=CC=CC(C)=C1[N+]([O-])=O HDFQKJQEWGVKCQ-UHFFFAOYSA-N 0.000 description 1
BYFNZOKBMZKTSC-UHFFFAOYSA-N 1,3-dimethyl-5-nitrobenzene Chemical compound CC1=CC(C)=CC([N+]([O-])=O)=C1 BYFNZOKBMZKTSC-UHFFFAOYSA-N 0.000 description 1
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
UPTOWXNJLZJTGD-UHFFFAOYSA-N 1,4-dimethoxy-2-nitrobenzene Chemical compound COC1=CC=C(OC)C([N+]([O-])=O)=C1 UPTOWXNJLZJTGD-UHFFFAOYSA-N 0.000 description 1
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 description 1
VOCGCNMEKJPLQQ-UHFFFAOYSA-N 1-(2-methylpropoxy)-2-nitrobenzene Chemical compound CC(C)COC1=CC=CC=C1[N+]([O-])=O VOCGCNMEKJPLQQ-UHFFFAOYSA-N 0.000 description 1
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 description 1
XGLGESCVNJSAQY-UHFFFAOYSA-N 1-ethoxy-2-nitrobenzene Chemical compound CCOC1=CC=CC=C1[N+]([O-])=O XGLGESCVNJSAQY-UHFFFAOYSA-N 0.000 description 1
YYRZQRXWASGXFT-UHFFFAOYSA-N 1-ethoxy-3,5-dinitrobenzene Chemical compound CCOC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 YYRZQRXWASGXFT-UHFFFAOYSA-N 0.000 description 1
NWPKEYHUZKMWKJ-UHFFFAOYSA-N 1-ethoxy-4-nitrobenzene Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1 NWPKEYHUZKMWKJ-UHFFFAOYSA-N 0.000 description 1
RPQSKHWNIKZEAI-UHFFFAOYSA-N 1-ethyl-2,4-dinitrobenzene Chemical compound CCC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RPQSKHWNIKZEAI-UHFFFAOYSA-N 0.000 description 1
PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 1
RXAKLPGKSXJZEF-UHFFFAOYSA-N 1-ethyl-3-nitrobenzene Chemical compound CCC1=CC=CC([N+]([O-])=O)=C1 RXAKLPGKSXJZEF-UHFFFAOYSA-N 0.000 description 1
WSZPRLKJOJINEP-UHFFFAOYSA-N 1-fluoro-2-[(2-fluoro-2,2-dinitroethoxy)methoxy]-1,1-dinitroethane Chemical compound [O-][N+](=O)C(F)([N+]([O-])=O)COCOCC(F)([N+]([O-])=O)[N+]([O-])=O WSZPRLKJOJINEP-UHFFFAOYSA-N 0.000 description 1
OTMLGCBMOMNGCV-UHFFFAOYSA-N 1-methoxy-3,5-dinitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 OTMLGCBMOMNGCV-UHFFFAOYSA-N 0.000 description 1
DRKFWQDBPGTSOO-UHFFFAOYSA-N 1-methyl-2-nitro-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C)C([N+]([O-])=O)=C1 DRKFWQDBPGTSOO-UHFFFAOYSA-N 0.000 description 1
SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
XXWIYOBCHKCWNT-UHFFFAOYSA-N 2,4-dimethoxy-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(OC)=C1 XXWIYOBCHKCWNT-UHFFFAOYSA-N 0.000 description 1
MCRYBELDVGNCFW-UHFFFAOYSA-N 2,4-dimethyl-3-nitroaniline Chemical compound CC1=CC=C(N)C(C)=C1[N+]([O-])=O MCRYBELDVGNCFW-UHFFFAOYSA-N 0.000 description 1
VSRYYONYIUUFFY-UHFFFAOYSA-N 2,4-dimethyl-6-nitroaniline Chemical compound CC1=CC(C)=C(N)C([N+]([O-])=O)=C1 VSRYYONYIUUFFY-UHFFFAOYSA-N 0.000 description 1
KJRCHILWKQLEBC-UHFFFAOYSA-N 2,4-dimethyl-6-nitrophenol Chemical compound CC1=CC(C)=C(O)C([N+]([O-])=O)=C1 KJRCHILWKQLEBC-UHFFFAOYSA-N 0.000 description 1
YSOKMOXAGMIZFZ-UHFFFAOYSA-N 2,4-dinitrophenetole Chemical compound CCOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YSOKMOXAGMIZFZ-UHFFFAOYSA-N 0.000 description 1
HHBUAAXHXWSZAG-UHFFFAOYSA-N 2,5-dimethyl-3-nitrophenol Chemical compound CC1=CC(O)=C(C)C([N+]([O-])=O)=C1 HHBUAAXHXWSZAG-UHFFFAOYSA-N 0.000 description 1
TZASZCQVZPLXHP-UHFFFAOYSA-N 2,6-dimethyl-3-nitrophenol Chemical compound CC1=CC=C([N+]([O-])=O)C(C)=C1O TZASZCQVZPLXHP-UHFFFAOYSA-N 0.000 description 1
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
JSOGDEOQBIUNTR-UHFFFAOYSA-N 2-(azidomethyl)oxirane Chemical compound [N-]=[N+]=NCC1CO1 JSOGDEOQBIUNTR-UHFFFAOYSA-N 0.000 description 1
LFQOLCFZVKRNMD-UHFFFAOYSA-N 2-ethoxy-1,3-dinitrobenzene Chemical compound CCOC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O LFQOLCFZVKRNMD-UHFFFAOYSA-N 0.000 description 1
HYQXQXJWUMOPKU-UHFFFAOYSA-N 2-ethoxy-1,4-dinitrobenzene Chemical compound CCOC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O HYQXQXJWUMOPKU-UHFFFAOYSA-N 0.000 description 1
SWASTJCUMFALOW-UHFFFAOYSA-N 2-ethyl-1,3-dinitrobenzene Chemical compound CCC1=C([N+]([O-])=O)C=CC=C1[N+]([O-])=O SWASTJCUMFALOW-UHFFFAOYSA-N 0.000 description 1
FMXDVBRYDYFVGS-UHFFFAOYSA-N 2-methoxy-1,3,5-trinitrobenzene Chemical compound COC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O FMXDVBRYDYFVGS-UHFFFAOYSA-N 0.000 description 1
MUBJXSCTPOBLCX-UHFFFAOYSA-N 2-methoxy-1,4-dinitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O MUBJXSCTPOBLCX-UHFFFAOYSA-N 0.000 description 1
GVBUHJSIDPIOBZ-UHFFFAOYSA-N 2-methoxy-3-nitroaniline Chemical compound COC1=C(N)C=CC=C1[N+]([O-])=O GVBUHJSIDPIOBZ-UHFFFAOYSA-N 0.000 description 1
KZBOXYKTSUUBTO-UHFFFAOYSA-N 2-methyl-1,4-dinitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1[N+]([O-])=O KZBOXYKTSUUBTO-UHFFFAOYSA-N 0.000 description 1
CFBYEGUGFPZCNF-UHFFFAOYSA-N 2-nitroanisole Chemical compound COC1=CC=CC=C1[N+]([O-])=O CFBYEGUGFPZCNF-UHFFFAOYSA-N 0.000 description 1
JKIFPWHZEZQCQA-UHFFFAOYSA-N 2-nitrobenzenethiol Chemical compound [O-][N+](=O)C1=CC=CC=C1S JKIFPWHZEZQCQA-UHFFFAOYSA-N 0.000 description 1
UUVUYEVFMFFSMP-UHFFFAOYSA-N 2-nitroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC[N+]([O-])=O UUVUYEVFMFFSMP-UHFFFAOYSA-N 0.000 description 1
KWMRZXLGCIDAGB-UHFFFAOYSA-N 2-nitroethyl prop-2-enoate Chemical compound [O-][N+](=O)CCOC(=O)C=C KWMRZXLGCIDAGB-UHFFFAOYSA-N 0.000 description 1
VDDQPZYMXOVQDD-UHFFFAOYSA-N 3,3-dinitropropyl prop-2-enoate Chemical compound [O-][N+](=O)C([N+]([O-])=O)CCOC(=O)C=C VDDQPZYMXOVQDD-UHFFFAOYSA-N 0.000 description 1
OXAUFLJQLMOTSU-UHFFFAOYSA-N 3,4-dimethyl-2-nitroaniline Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1C OXAUFLJQLMOTSU-UHFFFAOYSA-N 0.000 description 1
LRWWBVBRBWPHBA-UHFFFAOYSA-N 3,4-dimethyl-5-nitroaniline Chemical compound CC1=CC(N)=CC([N+]([O-])=O)=C1C LRWWBVBRBWPHBA-UHFFFAOYSA-N 0.000 description 1
INYDMNPNDHRJQJ-UHFFFAOYSA-N 3,4-dinitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 INYDMNPNDHRJQJ-UHFFFAOYSA-N 0.000 description 1
UDQLNMXIULDNCQ-UHFFFAOYSA-N 3,5-dimethyl-2-nitroaniline Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(N)=C1 UDQLNMXIULDNCQ-UHFFFAOYSA-N 0.000 description 1
YXNYMZXPUWOUJT-UHFFFAOYSA-N 3,5-dimethyl-2-nitrophenol Chemical compound CC1=CC(C)=C([N+]([O-])=O)C(O)=C1 YXNYMZXPUWOUJT-UHFFFAOYSA-N 0.000 description 1
VIQHHRZADKSPIM-UHFFFAOYSA-N 3,6-dimethyl-2-nitrophenol Chemical compound CC1=CC=C(C)C([N+]([O-])=O)=C1O VIQHHRZADKSPIM-UHFFFAOYSA-N 0.000 description 1
WGYFINWERLNPHR-UHFFFAOYSA-N 3-nitroanisole Chemical compound COC1=CC=CC([N+]([O-])=O)=C1 WGYFINWERLNPHR-UHFFFAOYSA-N 0.000 description 1
KGDIYDUZVHFMHQ-UHFFFAOYSA-N 4,5-dimethyl-2-nitrophenol Chemical compound CC1=CC(O)=C([N+]([O-])=O)C=C1C KGDIYDUZVHFMHQ-UHFFFAOYSA-N 0.000 description 1
GRXZQOTZXAKVLN-UHFFFAOYSA-N 4-methoxy-1,2-dinitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1 GRXZQOTZXAKVLN-UHFFFAOYSA-N 0.000 description 1
AXBVSRMHOPMXBA-UHFFFAOYSA-N 4-nitrothiophenol Chemical compound [O-][N+](=O)C1=CC=C(S)C=C1 AXBVSRMHOPMXBA-UHFFFAOYSA-N 0.000 description 1
VNXFNSPVHVKLPN-UHFFFAOYSA-N 6-methyl-2,3,4-trinitrophenol Chemical compound CC1=CC([N+]([O-])=O)=C([N+]([O-])=O)C([N+]([O-])=O)=C1O VNXFNSPVHVKLPN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
AGUIVNYEYSCPNI-UHFFFAOYSA-N N-methyl-N-picrylnitramine Chemical group [O-][N+](=O)N(C)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O AGUIVNYEYSCPNI-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
BNUHAJGCKIQFGE-UHFFFAOYSA-N Nitroanisol Chemical compound COC1=CC=C([N+]([O-])=O)C=C1 BNUHAJGCKIQFGE-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
WJIFPKPGOIUIFW-UHFFFAOYSA-N benzylbenzene;naphthalene Chemical compound C1=CC=CC2=CC=CC=C21.C=1C=CC=CC=1CC1=CC=CC=C1 WJIFPKPGOIUIFW-UHFFFAOYSA-N 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
LYAGTVMJGHTIDH-UHFFFAOYSA-N diethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCO[N+]([O-])=O LYAGTVMJGHTIDH-UHFFFAOYSA-N 0.000 description 1
KSHJAFFDLKPUMT-UHFFFAOYSA-N dinitro-ortho-cresol Chemical compound CC1=C(O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KSHJAFFDLKPUMT-UHFFFAOYSA-N 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
UQXKXGWGFRWILX-UHFFFAOYSA-N ethylene glycol dinitrate Chemical compound O=N(=O)OCCON(=O)=O UQXKXGWGFRWILX-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
QCOXCILKVHKOGO-UHFFFAOYSA-N n-(2-nitramidoethyl)nitramide Chemical compound [O-][N+](=O)NCCN[N+]([O-])=O QCOXCILKVHKOGO-UHFFFAOYSA-N 0.000 description 1
ARMSTQBMUHJXHU-UHFFFAOYSA-N n-(2-nitrophenyl)benzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(=O)C1=CC=CC=C1 ARMSTQBMUHJXHU-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
AAAUMZZBNYAFHL-UHFFFAOYSA-N nitro nitroformate Chemical class [O-][N+](=O)OC(=O)[N+]([O-])=O AAAUMZZBNYAFHL-UHFFFAOYSA-N 0.000 description 1
RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920005596 polymer binder Polymers 0.000 description 1
239000002491 polymer binding agent Substances 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920001004 polyvinyl nitrate Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
239000001120 potassium sulphate Substances 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012254 powdered material Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
AGCQZYRSTIRJFM-UHFFFAOYSA-N triethylene glycol dinitrate Chemical compound [O-][N+](=O)OCCOCCOCCO[N+]([O-])=O AGCQZYRSTIRJFM-UHFFFAOYSA-N 0.000 description 1
IPPYBNCEPZCLNI-UHFFFAOYSA-N trimethylolethane trinitrate Chemical compound [O-][N+](=O)OCC(C)(CO[N+]([O-])=O)CO[N+]([O-])=O IPPYBNCEPZCLNI-UHFFFAOYSA-N 0.000 description 1
239000000015 trinitrotoluene Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C06B45/04—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
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Dispersion Chemistry (AREA)
Molecular Biology (AREA)
Crystallography & Structural Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000541310A 1986-07-04 1987-07-03 Energetic materials containing heteroalicyclic nitramine compound Expired - Fee Related CA1325518C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB868616322A GB8616322D0 (en)	1985-07-08	1986-07-04	Conduit fitting
GB8616322		1986-07-04

Publications (1)

Publication Number	Publication Date
CA1325518C true CA1325518C (en)	1993-12-28

Family

ID=10600560

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000541310A Expired - Fee Related CA1325518C (en)	1986-07-04	1987-07-03	Energetic materials containing heteroalicyclic nitramine compound

Country Status (9)

Country	Link
AU (1)	AU663677B1 (de)
BE (1)	BE1005565A7 (de)
CA (1)	CA1325518C (de)
DE (1)	DE3744680C2 (de)
FR (1)	FR2664587B1 (de)
GB (1)	GB2243826B (de)
IT (1)	IT1235712B (de)
NL (1)	NL194964C (de)
SE (1)	SE500687C2 (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5540794A (en) *	1992-05-11	1996-07-30	Thiokol Corporation	Energetic binder and thermoplastic elastomer-based low vulnerability ammunition gun propellants with improved mechanical properties
SE470480B (sv) *	1992-10-02	1994-05-24	Bofors Explosives Ab	Drivmedel för Air bags
US5487851A (en) *	1993-12-20	1996-01-30	Thiokol Corporation	Composite gun propellant processing technique
US6214137B1 (en) *	1997-10-07	2001-04-10	Cordant Technologies Inc.	High performance explosive containing CL-20
WO1999035108A1 (de) *	1998-01-05	1999-07-15	Dynamit Nobel Gmbh Explosivstoff- Und Systemtechnik	Treibmittel
US6241833B1 (en) *	1998-07-16	2001-06-05	Alliant Techsystems, Inc.	High energy gun propellants
WO2001046091A1 (en) *	1999-12-22	2001-06-28	Doll, Daniel, W.	Reduced sensitivity melt-cast explosives
US7067024B2 (en)	2001-06-27	2006-06-27	Alliant Techsystems Inc.	Reduced sensitivity, melt-pourable TNT replacements
US6964714B2 (en)	2001-06-27	2005-11-15	Alliant Techsystems Inc.	Reduced sensitivity, melt-pourable tritonal replacements
DE102010020776B4 (de) *	2010-05-18	2015-03-05	Diehl Bgt Defence Gmbh & Co. Kg	Treibladung und Verfahren zu ihrer Herstellung

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3528864A (en) *	1965-09-21	1970-09-15	Us Navy	High impulse explosives containing tungsten
DE2329558C3 (de) *	1973-06-09	1978-10-05	Fraunhofer-Gesellschaft Zur Foerderung Der Angewandten Forschung E.V., 8000 Muenchen	Gießfähige Gasgeneratortreibstoffe
DE2365595A1 (de) *	1973-07-14	1975-10-02	Messerschmitt Boelkow Blohm	Hochleistungssprengkoerper
DE2336004A1 (de) *	1973-07-14	1975-02-13	Messerschmitt Boelkow Blohm	Hochleistungs-sprengstoff-formkoerper und verfahren zu ihrer herstellung
DE2709949C2 (de) *	1977-03-08	1982-09-16	Messerschmitt-Bölkow-Blohm GmbH, 8000 München	Kristalliner Hochleistungssprengstoff
US4092188A (en) *	1977-05-16	1978-05-30	Lovelace Alan M Acting Adminis	Nitramine propellants
DE2753555C1 (de) *	1977-12-01	1990-09-20	Dynamit Nobel Ag	Verwendung von polymeren Polynitroaromaten in Treibsaetzen
DE3023462A1 (de) *	1980-06-24	1984-02-23	Dynamit Nobel Ag, 5210 Troisdorf	Nitrierte arylaether

1987
- 1987-07-02 NL NL8715010A patent/NL194964C/nl not_active IP Right Cessation
- 1987-07-02 DE DE3744680A patent/DE3744680C2/de not_active Expired - Lifetime
- 1987-07-02 BE BE0000114A patent/BE1005565A7/fr active
- 1987-07-03 CA CA000541310A patent/CA1325518C/en not_active Expired - Fee Related
- 1987-07-06 AU AU75645/87A patent/AU663677B1/en not_active Ceased
- 1987-07-06 GB GB8715870A patent/GB2243826B/en not_active Expired - Lifetime
1988
- 1988-02-23 FR FR8802281A patent/FR2664587B1/fr not_active Expired - Fee Related
- 1988-04-18 IT IT8847864A patent/IT1235712B/it active
- 1988-05-25 SE SE8801944A patent/SE500687C2/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB8715870D0 (en)	1991-06-12
IT1235712B (it)	1992-09-24
NL194964C (nl)	2003-09-02
AU663677B1 (en)	1995-10-19
BE1005565A7 (fr)	1993-06-15
SE8801944D0 (sv)	1988-05-25
FR2664587A1 (fr)	1992-01-17
FR2664587B1 (fr)	1993-09-24
GB2243826A (en)	1991-11-13
DE3744680A1 (de)	1991-11-28
GB2243826B (en)	1992-03-25
SE500687C2 (sv)	1994-08-08
NL8715010A (nl)	1991-10-01
DE3744680C2 (de)	1996-10-02
SE8801944L (sv)	1991-09-06
NL194964B (nl)	2003-05-01
IT8847864A0 (it)	1988-04-18

Legal Events

Date	Code	Title	Description
2005-12-28	MKLA	Lapsed

Publication	Publication Date	Title
US5500060A (en)	1996-03-19	Energetic plasticized propellant
US7842144B1 (en)	2010-11-30	Methods of making double base casting powder
CA1325518C (en)	1993-12-28	Energetic materials containing heteroalicyclic nitramine compound
CA2053832C (en)	1999-09-07	Stable plasticizers for nitrocellulose/nitroguanidine-type compositions
US3362859A (en)	1968-01-09	Gas-generating compositions and their preparation
GB2371297A (en)	2002-07-24	Propellant compositions and propellants produced therefrom
KR101649517B1 (ko)	2016-08-19	니트라민 산화제를 포함하는 추진제 조성물
AU2014242706B2 (en)	2018-03-08	Insensitive munition propellants
US10526256B2 (en)	2020-01-07	Non-phthalate propellants
US3732130A (en)	1973-05-08	Gun propellant containing nonenergetic plasticizer,nitrocellulose and triaminoguanidine nitrate
US3732131A (en)	1973-05-08	Gun propellant containing nitroplasticized nitrocellulose and triaminoguanidine nitrate
GB2512346A (en)	2014-10-01	Non-phthalate propellants
EP2784054A1 (de)	2014-10-01	Unempfindliche Munitionstreibmittel
AU2017420106B2 (en)	2022-08-04	Composition for single-base propelling powder for ammunition and ammunition provided with such composition
AU784682B1 (en)	2006-06-01	Explosive compositions
JP5987446B2 (ja)	2016-09-07	トリプルベース発射薬組成物
US6645325B1 (en)	2003-11-11	Fast-burning nitrocellulose compositions
EP2784053A1 (de)	2014-10-01	Phthalatfreie Treibmittel
JP6402899B2 (ja)	2018-10-10	トリプルベース発射薬組成物
US2407597A (en)	1946-09-10	Explosive compositions comprising low freezing liquid mixtures of aromatic nitro-compounds
US8864923B1 (en)	2014-10-21	Ballistic modifier formulation for double base propellant
GB2512345A (en)	2014-10-01	Insensitive munition propellants
CZ35772U1 (cs)	2022-02-03	Heterogenní litý propelent do záchranných systémů
PL132419B1 (en)	1985-02-28	Mining nitroglycol explosive