WO2003102002A1 - Polyazides de silicium et procede pour les produire - Google Patents
Polyazides de silicium et procede pour les produire Download PDFInfo
- Publication number
- WO2003102002A1 WO2003102002A1 PCT/EP2003/005589 EP0305589W WO03102002A1 WO 2003102002 A1 WO2003102002 A1 WO 2003102002A1 EP 0305589 W EP0305589 W EP 0305589W WO 03102002 A1 WO03102002 A1 WO 03102002A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silicon
- iso
- alkyl groups
- general formula
- polyazide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 21
- 239000010703 silicon Substances 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- -1 phosphonium ion Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- 150000004985 diamines Chemical class 0.000 claims abstract description 8
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 7
- 229910052785 arsenic Inorganic materials 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
- 239000005049 silicon tetrachloride Substances 0.000 claims abstract description 7
- 229920000570 polyether Polymers 0.000 claims abstract description 6
- 239000003446 ligand Substances 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical group 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims abstract description 3
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 3
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 11
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 10
- SZJFGTWFLXTOHF-UHFFFAOYSA-N silicon tetraazide Chemical compound [N-]=[N+]=N[Si](N=[N+]=[N-])(N=[N+]=[N-])N=[N+]=[N-] SZJFGTWFLXTOHF-UHFFFAOYSA-N 0.000 claims description 10
- HKOAFLAGUQUJQG-UHFFFAOYSA-N 2-pyrimidin-2-ylpyrimidine Chemical class N1=CC=CN=C1C1=NC=CC=N1 HKOAFLAGUQUJQG-UHFFFAOYSA-N 0.000 claims description 9
- 150000002171 ethylene diamines Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003222 pyridines Chemical class 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 2
- 239000003049 inorganic solvent Substances 0.000 claims description 2
- 239000003495 polar organic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 230000035939 shock Effects 0.000 abstract description 2
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910003902 SiCl 4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000001069 Raman spectroscopy Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005474 detonation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
Definitions
- the invention relates to silicon polyazides of the general formula (I) (K + ) n [L 2 - n Si (N 3 ) 4 + n ] (n) " where n assumes the values 0 or 2, L for N-heterocycles, K for Alkali metals, NH 4 or ER 4 , where EN, P, As or Sb and
- R represent n- or iso-alkyl groups or phenyl groups, and processes for their preparation.
- Silicon tetraazide is known. It is produced by reacting silicon tetrachloride with, for example, sodium azide. Here, the reaction takes place in an anhydrous organic solvent such as. B. benzing instead.
- the result of the implementation is a hydrolysis-sensitive, highly explosive product.
- the total nitrogen content of these compounds is lower than in silicon tetraazide and they also contain Si-C bonds, so that these compounds do not appear to be suitable for further economic use, for example for the low-temperature synthesis of silicon nitride or silicon and for the release of large, hot amounts of gas.
- the invention is therefore based on the object of specifying silicon polyazides and processes for their preparation, to reduce or eliminate the thermal instability and the shock sensitivity of chemical compounds from the class of silicon polyazides with high nitrogen contents, in order to enable economical production and use of these compounds ,
- n takes the values 0 or 2
- K represents alkali metals, NH 4 or ER 4 ,
- R represent n- or iso-alkyl groups or phenyl groups.
- a process for the preparation of the compound having the general formula (I) is characterized in that silicon tetrachloride in the presence of a solvent initially with a compound of the general formula
- K ' is a cation, in particular an alkali metal ion, ammonium ion, a substituted ammonium or phosphonium ion, is reacted and then monodentate or polydentate, neutral or basic anionic ligands L are added, L being N- Heterocycles (such as pyridines, 2, 2'-bipyridines,
- R represent n- or iso-alkyl groups or phenyl groups and the alkyl groups have 1 to 5 carbon atoms.
- pyridines, 2, 2'-bipyridines and 2,2'-bipyrimidines are provided as N-heterocycles.
- the pyridines have n- or iso-alkyl groups or phenyl groups in the 2-, 3- or 4-position.
- the 2,2'-bipyridines have alkyl groups in 4,4'- or 5, 5 '-position and the 2, 2'-bipyrimidines in 4,4'- or 5,5'- or 6, 6 'position n- or iso-alkyl groups or phenyl groups.
- ethylenediamines or N- (n- or iso-) alkylated ethylenediamines are provided as diamines.
- All alkyl groups have 1 to 5 carbon atoms.
- alkyl-substituted ammonium ions are used for the substituted ammonium ions provided as K ', carbon contents of Ci to C 4 being provided.
- methyl- or phenyl-substituted phosphonium ions are advantageously used for the substituted phosphonium ions.
- pyridines, 2,2′-bipyridines and 2,2′-bipyrimidines are used for the N-heterocycles provided as ligand L.
- Pyridines which have n- or iso-alkyl groups or phenyl groups in the 2-, 3- or 4-position have proven to be very advantageous for the course of the reaction.
- the diamines are ethylenediamines or N- (n- or iso-) alkylated ethylenediamines, while 1,2-dimethoxyethane is used in particular as the polyether.
- alkyl-substituted N-heterocycles used are those which have alkyl groups with 1 to 5 C atoms.
- the reactions are carried out at temperatures between -30 ° C and + 40 ° C.
- the reactions are carried out in an aprotic polar solvent, these being carried out in an aprotic polar inorganic solvent, such as SO 2 at normal pressure below -10 ° C. and CO 2 at 35 bar below -20 ° C., or in an aprotic polar organic solvent such as acetonitrile, propionitrile, diethyl ether, benzene, toluene.
- an aprotic polar inorganic solvent such as SO 2 at normal pressure below -10 ° C. and CO 2 at 35 bar below -20 ° C.
- an aprotic polar organic solvent such as acetonitrile, propionitrile, diethyl ether, benzene, toluene.
- the compound of general formula (I) is used as a source for the release of silicon tetraazide.
- the silicon tetraazide can be released again by heating the compound (I) and thus serve to form large amounts of hot gas.
- the compound (I) must be heated to 200 to 400 ° C at normal pressure or in a vacuum.
- Test conditions The starting materials and solvents used during the synthesis must be absolutely free of water and oxygen. In the case of liquids, this is achieved by means of standard procedures that have been introduced and also by means of recondensation and pump-evacuation cycles. All synthesis operations are carried out with the help of a protective gas (argon or nitrogen), heated Pyrex glass vessels and a spatula with a Teflon coating. It is filtered through glass fiber filters.
- a protective gas argon or nitrogen
- heated Pyrex glass vessels and a spatula with a Teflon coating It is filtered through glass fiber filters.
- the silicon polyazide (N (PPh 3 ) 2 ) 2 [Si (N 3 ) 6 ] is placed in a high vacuum apparatus made of glass and stainless steel and after application of a high vacuum (p ⁇ 1-10 -3 mbar) at 30 K / min the decomposition temperature of 320 ° C warmed.
- the crystals of 2, 2 '-bipyridine gradually dissolve to give an abso-
- the solution is clear and colorless, and cloudiness occurs for the first time from approx. -10 ° C. It quickly increases until the ambient temperature is reached.
- the precipitated substance is filtered off (257 mg) and the clear colorless filtrate is concentrated to approx 0.5 ml, where crystallization occurs
- the isolated substance is first recrystallized in tetrahydrofuran and then in acetonitrile by cooling Cooling of solutions saturated at room temperature.
- the yield after recrystallization from tetrahydrofuran is 81% and after recrystallization from acetonitrile it is 60%.
- the information relates to SiCl 4 .
- 453 mg of colorless, air-sensitive small single crystals of [(2,2'-bipy) Si (N 3 ) 4 ] appearing in a thick layer slightly rose.
- the compound was identified by IR and NMR spectroscopy, elemental analysis, mass spectrometry, thermal analysis and X-ray single crystal structure analysis.
- the compound melts at 211-212 ° C with sublimation and without decomposition, as was proven by comparison of IR and NMR spectra with an authentic sample. Heating the material to an even higher temperature leads to detonation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
La présente invention concerne des polyazides de silicium de formule générale (I) (K+)n[L2-nSi(N3) 4+n] (n)- dans laquelle n représente 0 ou 2, L représente des N-hétérocycles, K représente des métaux alcalins, NH4 ou ER4, avec E représentant N, P, As ou Sb et R représentant des groupes n- ou isoalkyle ou des groupes phényle, ainsi que des procédés pour les produire. Les procédés pour les produire consistent à mettre en réaction du tétrachlorure de silicium, en présence d'un solvant, d'abord avec un composé de formule générale (II) K'(N3) dans laquelle K' représente un cation, notamment un ion de métal alcalin, un ion d'ammonium ou un ion d'ammonium ou de phosphonium substitué, puis est mélangé avec un ligand L neutre ou basique anionique, monodentelé ou polydentelé, avec L représentant des N-hétérocycles, des diamines ou des polyesters, ou consistent à mettre en réaction du tétrachlorure de silicium avec des composés de formule générale (III) (ER4)+(N3)- afin de le transformer directement en (I), avec E représentant N, P, As ou Sb et R représentant des groupes n- ou isoalkyle ou des groupes phényle, les groupes alkyle présentant de 1 à 5 atomes de C. Les nouveaux polyazides de silicium et les procédés pour les produire selon cette invention permettent de réduire ou de supprimer l'instabilité thermique et la sensibilité aux chocs de composés chimiques de la classe des polyazides de silicium présentant de hautes teneurs en azote et d'obtenir ainsi une production et une utilisation économiques de ces composés.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003237700A AU2003237700A1 (en) | 2002-05-31 | 2003-05-27 | Silicon polyazides and a method for their production |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10225175.4 | 2002-05-31 | ||
| DE10225175 | 2002-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003102002A1 true WO2003102002A1 (fr) | 2003-12-11 |
Family
ID=29594302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2003/005589 WO2003102002A1 (fr) | 2002-05-31 | 2003-05-27 | Polyazides de silicium et procede pour les produire |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003237700A1 (fr) |
| WO (1) | WO2003102002A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010034317A1 (fr) | 2008-09-26 | 2010-04-01 | As Sivex International | Procédé et système pour vérifier et gérer une file de véhicules au passage de frontière |
| US8809566B2 (en) | 2008-11-11 | 2014-08-19 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232958A (en) * | 1961-11-03 | 1966-02-01 | American Potash & Chem Corp | Metalloid azides and process for preparing the same |
| JPH01143878A (ja) * | 1987-12-01 | 1989-06-06 | Nippon Tokushu Kagaku Kogyo Kk | ケイ素アジド化合物の製造方法 |
-
2003
- 2003-05-27 AU AU2003237700A patent/AU2003237700A1/en not_active Abandoned
- 2003-05-27 WO PCT/EP2003/005589 patent/WO2003102002A1/fr not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232958A (en) * | 1961-11-03 | 1966-02-01 | American Potash & Chem Corp | Metalloid azides and process for preparing the same |
| JPH01143878A (ja) * | 1987-12-01 | 1989-06-06 | Nippon Tokushu Kagaku Kogyo Kk | ケイ素アジド化合物の製造方法 |
Non-Patent Citations (4)
| Title |
|---|
| DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; WIBERG, EGON ET AL: "Silicon tetraazide, Si(N3)4", XP002251601, retrieved from STN Database accession no. 49:3965 * |
| FILIPPOU, ALEXANDER C. ET AL: "The Hexaazidosilicate(IV) Ion: Synthesis, Properties, and Molecular Structure", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2002), 124(42), 12396-12397, XP002251600 * |
| PATENT ABSTRACTS OF JAPAN vol. 013, no. 402 (C - 633) 6 September 1989 (1989-09-06) * |
| ZEITSCHRIFT FUER NATURFORSCHUNG (1954), 9B, 500 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010034317A1 (fr) | 2008-09-26 | 2010-04-01 | As Sivex International | Procédé et système pour vérifier et gérer une file de véhicules au passage de frontière |
| US8809566B2 (en) | 2008-11-11 | 2014-08-19 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003237700A1 (en) | 2003-12-19 |
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