NO137008B - Bornitridslipekorn og fremgangsm}te ved fremstilling derav. - Google Patents
Bornitridslipekorn og fremgangsm}te ved fremstilling derav. Download PDFInfo
- Publication number
- NO137008B NO137008B NO741414A NO741414A NO137008B NO 137008 B NO137008 B NO 137008B NO 741414 A NO741414 A NO 741414A NO 741414 A NO741414 A NO 741414A NO 137008 B NO137008 B NO 137008B
- Authority
- NO
- Norway
- Prior art keywords
- benzothiadiazine
- dihydro
- sulfamyl
- general formula
- carboxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims description 10
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000002934 diuretic Substances 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- BOZSDDFQWJUBNG-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1S(N)(=O)=O BOZSDDFQWJUBNG-UHFFFAOYSA-N 0.000 description 1
- JVGZNWQUTQMUFN-UHFFFAOYSA-N C(CCCC)C1NS(C2=C(N1)C=CC=C2)(=O)=O Chemical compound C(CCCC)C1NS(C2=C(N1)C=CC=C2)(=O)=O JVGZNWQUTQMUFN-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- PFRBORHNFYMVOA-UHFFFAOYSA-N methyl 6-chloro-2-methyl-1,1-dioxo-7-sulfamoyl-3,4-dihydro-1$l^{6},2,4-benzothiadiazine-3-carboxylate Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(C(=O)OC)NC2=C1 PFRBORHNFYMVOA-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/58—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides
- C04B35/583—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides based on boron nitride
- C04B35/5831—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on borides, nitrides, i.e. nitrides, oxynitrides, carbonitrides or oxycarbonitrides or silicides based on boron nitride based on cubic boron nitrides or Wurtzitic boron nitrides, including crystal structure transformation of powder
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/06—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron
- C01B21/064—Binary compounds of nitrogen with metals, with silicon, or with boron, or with carbon, i.e. nitrides; Compounds of nitrogen with more than one metal, silicon or boron with boron
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/14—Anti-slip materials; Abrasives
- C09K3/1409—Abrasive particles per se
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/14—Anti-slip materials; Abrasives
- C09K3/1436—Composite particles, e.g. coated particles
- C09K3/1445—Composite particles, e.g. coated particles the coating consisting exclusively of metals
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/51—Particles with a specific particle size distribution
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Ceramic Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Composite Materials (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Polishing Bodies And Polishing Tools (AREA)
- Ceramic Products (AREA)
- Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
- Disintegrating Or Milling (AREA)
- Solid-Phase Diffusion Into Metallic Material Surfaces (AREA)
Description
Fremgangsmåte for fremstilling av 3-carboksy-7-sulfamyl-3,4-dihydro-1, 2, 4-benzothiadiazin-l,l-dioksyder.
Nærværende oppfinnelse vedrører en
fremgangsmåte for fremstilling av 3-carb-oksy-7-sulfamyl-3, 4-dihydro-l, 2,4,-benzothiadiazin-1, 1-dioksyder med den generelle formel:
hvor X betegner et klor- eller bromatom
eller en trifluormetyllrest,, R et hydrogenatom, en metyll- eller etyllgruppe og R' en
alkylrest med 1 til 4 carbonatomer. Forbindelsene opnas når man på i og for seg
kjent måte enten:
(a) omsetter et 3-carboksy-7-sulfamyl-3, 4,-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd med den generelle formel:
med et overskudd av en alkohol med den generelle formel R'OH i nærvær av klor-hydrogen eller: (b) bringer et mol 3-carboksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd med den generelle formel:
til reaksjon med et eller 2 mol diazometan.
Man utfører fremgangsmåten (a) hen-siktsmessig ved forhøyet temperatur, fortrinnsvis ved ca. tilbakeløpstemperatur. Etter avslutning av reaksjonen lar man reaksjonsblandingen avkjøle seg, hvorved 3-carbalkoksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksydderivat fel-les ut, som filtreres fra og som kan renses ved omkrystallisering. Man kan imidlertid også etter avslutning av reaksjonen for-dampe det overflødige oppløsningsmiddel og omkrystallisere resten.
Fremgangsmåten varianten (b) gjen-nomføres ved romtemperatur og i nærvær av egnet oppløsningsmiddel. Etter avslutning av reaksjonen trekker man av opp-løsningsmidler og etter omkrystallisering av resten fra methanol eller et annet egnet oppløsningsmiddel får man alt etter mengden diazomethan, som ble isatt pr. mol av det som utgangsstoff anvendte 3-carboksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyder en forbindelse med den generelle formel: eller
Som utgangsmateriale anvendes 3-carboksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-1, 1-dioksyd eller de som utgangsmaterialer dioksyder fremstillt idet man oppvarmer en blanding av vann og ekvimolare mengder av et i 5-stilling med resten X substituert 2,4-disulfamylaniliner, hvis sulfamylgruppe i 2-stilling kan være substituert med en metyll- eller etyllgruppe, og glyoksyllsyre (fortrinnsvis et alkali-salt av syre) til koking og under tilbakeløp, inntil reaksjonen er fullstendig. Etter av-kjøling og ansyring av reaksjonsblandingen skiller det i 6-stilling med resten X og i 2-stilling med en metyll- eller etyllgruppe substituerte 3-carboksy-7-sulfamyl-3, 4-dihydro-1, 2, 4-benzothiadiazin-l,1- dioksyd seg fra som krystalline stoffer, som filtreres fra og blir omkrystallisert fra vann eller alkohol.
De ifølge oppfinnelsen fremstilte 3-carboksyforbindelser er krystalline stoffer som meget godt lar seg administrere som diuretica ved anvendelse i ikke-giftige mengder såvel oral som ved injeksjon.
Til sammenligning av den diuretiske virkning av de ifølge oppfinnelsen opp-nåelige forbindelser og det kjente 6-klor-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyder ble forbindelsene admi-nistrert oralt til rotter hvorved den kjente forbindelse ble anvendt som standard (diuretisk aktiv 1). Beregnet på den utskilte urin ble aktiviteten for forbindelser med den generelle formel:
funnet som følger:
Substituenter:
X R' Diuretisk
virksomhet
Eksempel 1.
3-carbometoksy-6-klor-7-sulfamyl-3, 4-dihydro-1, 2, 4-benzothiadiazin-l, 1-dl-oksyd.
Til en oppløsning av 1,71 g (0,005 mol) av 3-carboksy-6-klor-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd i 10 ml metanol ble tilsatt porsjonsvis under omrøring ved romtemperatur, 0,21 g (0,005 mol) av diazometan oppløst i 40 ml eter. Oppløsningsmidlet ble deretter fordampet og residuet omkrystallisert fra metanol for å gi det ovenfor angitte produkt som et krystallinsk fast stoff som smelter ved 234—236°C utbytte 88 pst. Analyse beregnet for C9H10ClN3O6S2.
Beregnet C= 30,4 pst., H=2,8 pst.
Funnet C=30,4 pst., H=3,0 pst.
Eksempel 2.
3-carbometoksy-6-klor-2-metyll-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd
Denne forbindelse ble fremstilt på samme måte som beskrevet i eksempel 1, unntatt at mengden av diazometan som ble anvendt, ble fordoblet. Forbindelsen ble funnet å smelte ved 224—225°C. Utbytte 82 pst. Analyse beregnet for C10H12ClN3O0S2. Beregnet C=32,5 pst., H=3,2 pst. Funnet C=32,6 pst., H=3,5 pst.
Eksempel 3.
Ved en alternativ fremstillingsmetode ble 20 g (0,053 mol) av 3-carboksy-6-klor-2-metyll-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-1, 1-dioksyd monohydrat (smeltepunkt 154°C) oppløst i 100 ml metanol, til hvilken var tilsatt 6 g acetondime-tylacetal og 2 ml konsentrert saltsyre. Deretter ble to 6 g porsjoner acetal tilsatt ved romtemperatur med en times mellomrom. Den resulterende blanding ble oppvarmet over natt ved 50°C. Oppløsningsmidlene ble derpå fjernet under redusert trykk og residuet omkrystallisert fra metanol-vann blanding for å oppnå det ønskede 3-car-bometoksy-6 -klor-2 -metyll-7 -sulf amyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd, som smelter ved 225°C. Utbytte 81 pst.
Claims (1)
- Fremgangsmåte for fremstilling av 3-carbalkoksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyder med den generelle formel:hvor X er et klor- eller bromatom eller en trifluormetyllrest, R et hydrogenatom, en metyll- eller etyllgruppe og R' en alkylrest med 1 til 4 carbonatomer, karakterisert ved at man på i og for seg kjent måte enten: (a) omsetter et 3-carboksy-7-sulfamyl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd med den generelle formel: med et overskudd av en alkohol med den generelle formel R'OH i nærvær av klor-hydrogen eller: (b) bringer et mol 3-carboksy-7-sulfa-myl-3, 4-dihydro-l, 2, 4-benzothiadiazin-l, 1-dioksyd med den generelle formel: til reaksjon med et eller 2 mol diazomethan.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US352884A US3881890A (en) | 1973-04-20 | 1973-04-20 | Abrasive boron nitride particles containing phosphorus |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO741414L NO741414L (no) | 1974-10-22 |
| NO137008B true NO137008B (no) | 1977-09-05 |
| NO137008C NO137008C (no) | 1977-12-14 |
Family
ID=23386894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO741414A NO137008C (no) | 1973-04-20 | 1974-04-19 | Bornitridslipekorn og fremgangsm}te ved fremstilling derav |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3881890A (no) |
| JP (1) | JPS5421033B2 (no) |
| AR (1) | AR201861A1 (no) |
| AT (1) | AT341366B (no) |
| BE (1) | BE813615A (no) |
| BR (1) | BR7403088D0 (no) |
| CA (1) | CA1026105A (no) |
| CH (1) | CH602484A5 (no) |
| DE (1) | DE2416267A1 (no) |
| DK (1) | DK142051B (no) |
| ES (1) | ES425419A1 (no) |
| FR (1) | FR2226474B1 (no) |
| GB (1) | GB1466180A (no) |
| IE (1) | IE39083B1 (no) |
| IL (1) | IL44457A (no) |
| IN (1) | IN142181B (no) |
| IT (1) | IT1009877B (no) |
| LU (1) | LU69887A1 (no) |
| NL (1) | NL7405385A (no) |
| NO (1) | NO137008C (no) |
| SE (1) | SE420307B (no) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148199A (en) * | 1978-05-12 | 1979-11-20 | Hitachi Ltd | Production of cubic boron nitride fine powder |
| DE3030362C2 (de) * | 1980-08-11 | 1986-11-27 | Institut sverchtverdych materialov Akademii Nauk Ukrainskoj SSR, Kiew/Kiev | Verfahren zur Herstellung von kubischem Bornitrid |
| FR2495597A1 (fr) * | 1980-08-26 | 1982-06-11 | Inst Sverkhtverdykh Mat | Procede de preparation de nitrure de bore cubique et produit obtenu par ledit procede |
| US4349517A (en) * | 1980-10-21 | 1982-09-14 | Lysanov Vladislav S | Method of producing cubic boron nitride |
| JPS58120505A (ja) * | 1982-01-06 | 1983-07-18 | Showa Denko Kk | 立方晶窒化ホウ素粒子 |
| AT386538B (de) * | 1986-03-27 | 1988-09-12 | Tyrolia Freizeitgeraete | Sicherheitsskibindung |
| US5178644A (en) * | 1992-01-23 | 1993-01-12 | Cincinnati Milacron Inc. | Method for making vitreous bonded abrasive article and article made by the method |
| GB201105381D0 (en) * | 2011-03-30 | 2011-05-11 | Element Six Ltd | Cubic boron nitride grit and tools comprising same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947617A (en) * | 1958-01-06 | 1960-08-02 | Gen Electric | Abrasive material and preparation thereof |
| US3036907A (en) * | 1959-09-22 | 1962-05-29 | Norton Co | Metal bonded abrasive composition |
| NL302348A (no) * | 1963-01-17 | |||
| US3192015A (en) * | 1963-04-01 | 1965-06-29 | Gen Electric | Growth of large cubic form of boron nitride crystals |
| US3233988A (en) * | 1964-05-19 | 1966-02-08 | Gen Electric | Cubic boron nitride compact and method for its production |
-
1973
- 1973-04-20 US US352884A patent/US3881890A/en not_active Expired - Lifetime
-
1974
- 1974-03-20 IE IE592/74A patent/IE39083B1/xx unknown
- 1974-03-20 IN IN610/CAL/1974A patent/IN142181B/en unknown
- 1974-03-21 IL IL44457A patent/IL44457A/en unknown
- 1974-03-21 GB GB1272074A patent/GB1466180A/en not_active Expired
- 1974-04-03 DE DE2416267A patent/DE2416267A1/de not_active Withdrawn
- 1974-04-04 FR FR7411972A patent/FR2226474B1/fr not_active Expired
- 1974-04-04 CA CA196,788A patent/CA1026105A/en not_active Expired
- 1974-04-11 BE BE143114A patent/BE813615A/xx unknown
- 1974-04-15 JP JP4264574A patent/JPS5421033B2/ja not_active Expired
- 1974-04-17 BR BR3088/74A patent/BR7403088D0/pt unknown
- 1974-04-17 IT IT21546/74A patent/IT1009877B/it active
- 1974-04-17 ES ES425419A patent/ES425419A1/es not_active Expired
- 1974-04-18 CH CH539574A patent/CH602484A5/xx not_active IP Right Cessation
- 1974-04-18 DK DK213474AA patent/DK142051B/da unknown
- 1974-04-18 LU LU69887A patent/LU69887A1/xx unknown
- 1974-04-19 SE SE7405316A patent/SE420307B/xx unknown
- 1974-04-19 NO NO741414A patent/NO137008C/no unknown
- 1974-04-19 AT AT327074A patent/AT341366B/de not_active IP Right Cessation
- 1974-04-19 AR AR253362A patent/AR201861A1/es active
- 1974-04-19 NL NL7405385A patent/NL7405385A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL44457A0 (en) | 1974-06-30 |
| BE813615A (fr) | 1974-07-31 |
| FR2226474A1 (no) | 1974-11-15 |
| IE39083B1 (en) | 1978-08-02 |
| IT1009877B (it) | 1976-12-20 |
| NL7405385A (no) | 1974-10-22 |
| GB1466180A (en) | 1977-03-02 |
| NO741414L (no) | 1974-10-22 |
| ATA327074A (de) | 1977-05-15 |
| CH602484A5 (no) | 1978-07-31 |
| IE39083L (en) | 1974-10-20 |
| JPS5421033B2 (no) | 1979-07-27 |
| JPS5019086A (no) | 1975-02-28 |
| FR2226474B1 (no) | 1978-01-13 |
| DK142051C (no) | 1981-01-12 |
| AT341366B (de) | 1978-02-10 |
| CA1026105A (en) | 1978-02-14 |
| IL44457A (en) | 1976-07-30 |
| ES425419A1 (es) | 1976-06-01 |
| SE420307B (sv) | 1981-09-28 |
| LU69887A1 (no) | 1974-07-18 |
| IN142181B (no) | 1977-06-11 |
| BR7403088D0 (pt) | 1974-11-19 |
| AU6756174A (en) | 1975-10-09 |
| US3881890A (en) | 1975-05-06 |
| AR201861A1 (es) | 1975-04-24 |
| NO137008C (no) | 1977-12-14 |
| DE2416267A1 (de) | 1974-11-07 |
| DK142051B (da) | 1980-08-18 |
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