IL99619A - Process for treating dinitroanilines with sulfite to reduce impurities and to reduce the ability to produce nitrosamines - Google Patents
Process for treating dinitroanilines with sulfite to reduce impurities and to reduce the ability to produce nitrosaminesInfo
- Publication number
- IL99619A IL99619A IL9961991A IL9961991A IL99619A IL 99619 A IL99619 A IL 99619A IL 9961991 A IL9961991 A IL 9961991A IL 9961991 A IL9961991 A IL 9961991A IL 99619 A IL99619 A IL 99619A
- Authority
- IL
- Israel
- Prior art keywords
- dinitroaniline
- sulfite
- dinitroanilines
- nitrosamines
- impurities
- Prior art date
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000008569 process Effects 0.000 title claims abstract description 23
- 239000012535 impurity Substances 0.000 title claims abstract description 18
- 150000004005 nitrosamines Chemical class 0.000 title claims abstract description 16
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 title description 19
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 claims abstract description 47
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims description 23
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims description 13
- 235000010265 sodium sulphite Nutrition 0.000 claims description 11
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 claims description 7
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 claims description 3
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 3
- OFDYMSKSGFSLLM-UHFFFAOYSA-N Dinitramine Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O OFDYMSKSGFSLLM-UHFFFAOYSA-N 0.000 claims description 3
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 claims description 3
- 235000019252 potassium sulphite Nutrition 0.000 claims description 3
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005587 Oryzalin Substances 0.000 claims description 2
- 239000005591 Pendimethalin Substances 0.000 claims description 2
- RSVPPPHXAASNOL-UHFFFAOYSA-N Prodiamine Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C(N)=C1[N+]([O-])=O RSVPPPHXAASNOL-UHFFFAOYSA-N 0.000 claims description 2
- ITVQAKZNYJEWKS-UHFFFAOYSA-N Profluralin Chemical compound [O-][N+](=O)C=1C=C(C(F)(F)F)C=C([N+]([O-])=O)C=1N(CCC)CC1CC1 ITVQAKZNYJEWKS-UHFFFAOYSA-N 0.000 claims description 2
- LKVOXDJKFRBRQV-UHFFFAOYSA-N n-(dimethyl-$l^{4}-sulfanylidene)-4-(dipropylamino)-3,5-dinitrobenzenesulfonamide Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(=O)(=O)N=S(C)C)C=C1[N+]([O-])=O LKVOXDJKFRBRQV-UHFFFAOYSA-N 0.000 claims description 2
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 claims description 2
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 2
- NEKOXWSIMFDGMA-UHFFFAOYSA-N Isopropalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(C)C)C=C1[N+]([O-])=O NEKOXWSIMFDGMA-UHFFFAOYSA-N 0.000 claims 1
- -1 chlornidine Chemical compound 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 7
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000012071 phase Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 6
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
- YLKFDHTUAUWZPQ-UHFFFAOYSA-N N-Nitrosodi-n-propylamine Chemical compound CCCN(N=O)CCC YLKFDHTUAUWZPQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- WUUWDHBPRAWSAU-UHFFFAOYSA-N 1,2-dichloro-3-nitro-4-(trifluoromethyl)benzene Chemical class [O-][N+](=O)C1=C(Cl)C(Cl)=CC=C1C(F)(F)F WUUWDHBPRAWSAU-UHFFFAOYSA-N 0.000 description 1
- QCUYQDLZRUPZRU-UHFFFAOYSA-N 1-(chloromethyl)-2,3,4-trifluoro-5,6-dinitrobenzene Chemical class [O-][N+](=O)C1=C(F)C(F)=C(F)C(CCl)=C1[N+]([O-])=O QCUYQDLZRUPZRU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ARSLNKYOPNUFFY-UHFFFAOYSA-L barium sulfite Chemical compound [Ba+2].[O-]S([O-])=O ARSLNKYOPNUFFY-UHFFFAOYSA-L 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- BBLSYMNDKUHQAG-UHFFFAOYSA-L dilithium;sulfite Chemical compound [Li+].[Li+].[O-]S([O-])=O BBLSYMNDKUHQAG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000001031 gas chromatography-thermal energy analyser Methods 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- XQRJTYUPZVTBDU-UHFFFAOYSA-N imino-dimethyl-sulfonyl-lambda6-sulfane Chemical compound S(=O)(=O)=S(=N)(C)C XQRJTYUPZVTBDU-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- JESHZQPNPCJVNG-UHFFFAOYSA-L magnesium;sulfite Chemical compound [Mg+2].[O-]S([O-])=O JESHZQPNPCJVNG-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- JTGBFBLUFMOGMQ-UHFFFAOYSA-N n,n-bis(1-chloroethyl)-4-methyl-2,6-dinitroaniline Chemical compound CC(Cl)N(C(C)Cl)C1=C([N+]([O-])=O)C=C(C)C=C1[N+]([O-])=O JTGBFBLUFMOGMQ-UHFFFAOYSA-N 0.000 description 1
- AUIKJTGFPFLMFP-UHFFFAOYSA-N n,n-di(propan-2-yl)nitrous amide Chemical compound CC(C)N(N=O)C(C)C AUIKJTGFPFLMFP-UHFFFAOYSA-N 0.000 description 1
- UYFBSIJFMJLIAZ-UHFFFAOYSA-N n-(cyclopropylmethyl)aniline Chemical compound C1CC1CNC1=CC=CC=C1 UYFBSIJFMJLIAZ-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 231100000378 teratogenic Toxicity 0.000 description 1
- 230000003390 teratogenic effect Effects 0.000 description 1
- HSYFJDYGOJKZCL-UHFFFAOYSA-L zinc;sulfite Chemical compound [Zn+2].[O-]S([O-])=O HSYFJDYGOJKZCL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/52—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/591,590 US5196585A (en) | 1990-10-02 | 1990-10-02 | Process for treating dinitroanilines with sulfite to reduce impurities and to reduce the ability to produce nitrosamines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL99619A true IL99619A (en) | 1995-12-31 |
Family
ID=24367069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9961991A IL99619A (en) | 1990-10-02 | 1991-10-01 | Process for treating dinitroanilines with sulfite to reduce impurities and to reduce the ability to produce nitrosamines |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5196585A (de) |
| EP (1) | EP0479384B1 (de) |
| JP (1) | JP2992384B2 (de) |
| KR (1) | KR100195771B1 (de) |
| AT (1) | ATE110053T1 (de) |
| AU (1) | AU639141B2 (de) |
| BR (1) | BR9104242A (de) |
| CA (1) | CA2052560C (de) |
| DE (1) | DE69103504T2 (de) |
| DK (1) | DK0479384T3 (de) |
| ES (1) | ES2059043T3 (de) |
| FI (1) | FI107147B (de) |
| HU (1) | HU210906B (de) |
| IL (1) | IL99619A (de) |
| MX (1) | MX9101401A (de) |
| RO (1) | RO109843B1 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1261259B (it) * | 1993-09-13 | 1996-05-09 | Finchimica Srl | Procedimento per la preparazione di ethalfluralin |
| US5510534A (en) * | 1995-01-04 | 1996-04-23 | Atanor S.A. | Process for reducing the nitrosamine content of herbicides |
| US5728881A (en) * | 1997-03-05 | 1998-03-17 | Srm Chemical, Ltd. Co. | Process for preparing trifluralin |
| FR2760446B1 (fr) * | 1997-03-07 | 1999-05-14 | Rhodia Chimie Sa | Procede de decoloration d'effluents aqueux comprenant des amines aromatiques |
| US6004482A (en) * | 1997-12-24 | 1999-12-21 | Bayer Corporation | Stable aromatic amine composition, and a process for preparing color stable aromatic amines |
| US5922915A (en) * | 1998-05-11 | 1999-07-13 | Srm Chemical, Ltd., Co. | Process for removing N-nitroso compounds from organo-amine compositions including dinitroaniline herbicides |
| CN101891634B (zh) * | 2010-07-20 | 2013-04-03 | 涟水永安化工有限公司 | 一种二甲戊灵的提纯方法 |
| CN102701989B (zh) * | 2012-05-24 | 2013-11-13 | 山东华阳农药化工集团有限公司 | 二硝基苯胺类除草剂中的亚硝胺脱除方法 |
| CN102766056B (zh) * | 2012-08-13 | 2014-07-02 | 江西盾牌化工有限责任公司 | 一种化学除草剂仲丁灵原药含量达90±1%的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA697087A (en) * | 1964-11-03 | W. Buls Vernon | Decolorization process | |
| US4139562A (en) * | 1978-03-13 | 1979-02-13 | Mitsui Toatsu Chemicals, Inc. | Process for purifying crude p-aminophenol |
| US4440962A (en) * | 1982-04-22 | 1984-04-03 | Oxon Italia S.P.A. | Process for removing nitrosating agents from 1-chloro-2,6-dinitro-4-(trifluoromethyl) benzene |
| US4501608A (en) * | 1983-05-16 | 1985-02-26 | Eli Lilly And Company | Nitrosamine inhibition |
| DE3345157A1 (de) * | 1983-12-14 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von nitrosaminfreien n,n-disubstituierten nitroaromatischen aminen und deren stabilisierung gegen nitrosaminbildung |
| IL78948A (en) * | 1985-06-06 | 1991-03-10 | Finchimica Srl | Process for purifying crude trifluralin |
| IT1190440B (it) * | 1985-12-18 | 1988-02-16 | Finchimica Spa | Procedimento migliorato per la purificazione della trifluralina |
| AU608808B2 (en) * | 1987-03-02 | 1991-04-18 | Ici Australia Operations Proprietary Limited | Process for removing impurity |
-
1990
- 1990-10-02 US US07/591,590 patent/US5196585A/en not_active Expired - Fee Related
-
1991
- 1991-09-27 BR BR919104242A patent/BR9104242A/pt not_active IP Right Cessation
- 1991-09-30 AU AU84884/91A patent/AU639141B2/en not_active Ceased
- 1991-10-01 CA CA002052560A patent/CA2052560C/en not_active Expired - Fee Related
- 1991-10-01 JP JP3280690A patent/JP2992384B2/ja not_active Expired - Lifetime
- 1991-10-01 AT AT91202557T patent/ATE110053T1/de not_active IP Right Cessation
- 1991-10-01 DE DE69103504T patent/DE69103504T2/de not_active Expired - Fee Related
- 1991-10-01 IL IL9961991A patent/IL99619A/en active IP Right Grant
- 1991-10-01 DK DK91202557.4T patent/DK0479384T3/da active
- 1991-10-01 HU HU913133A patent/HU210906B/hu not_active IP Right Cessation
- 1991-10-01 RO RO148483A patent/RO109843B1/ro unknown
- 1991-10-01 EP EP91202557A patent/EP0479384B1/de not_active Expired - Lifetime
- 1991-10-01 KR KR1019910017186A patent/KR100195771B1/ko not_active Expired - Fee Related
- 1991-10-01 ES ES91202557T patent/ES2059043T3/es not_active Expired - Lifetime
- 1991-10-01 FI FI914610A patent/FI107147B/fi active
- 1991-10-01 MX MX9101401A patent/MX9101401A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI914610L (fi) | 1992-04-03 |
| HU913133D0 (en) | 1992-01-28 |
| DE69103504T2 (de) | 1994-12-08 |
| KR920007982A (ko) | 1992-05-27 |
| DE69103504D1 (de) | 1994-09-22 |
| US5196585A (en) | 1993-03-23 |
| BR9104242A (pt) | 1992-06-02 |
| CA2052560A1 (en) | 1992-04-03 |
| AU639141B2 (en) | 1993-07-15 |
| AU8488491A (en) | 1992-04-09 |
| JPH04264059A (ja) | 1992-09-18 |
| DK0479384T3 (da) | 1995-01-02 |
| ES2059043T3 (es) | 1994-11-01 |
| ATE110053T1 (de) | 1994-09-15 |
| FI914610A0 (fi) | 1991-10-01 |
| FI107147B (fi) | 2001-06-15 |
| HU210906B (en) | 1995-09-28 |
| HUT61720A (en) | 1993-03-01 |
| KR100195771B1 (ko) | 1999-06-15 |
| MX9101401A (es) | 1992-06-30 |
| JP2992384B2 (ja) | 1999-12-20 |
| EP0479384B1 (de) | 1994-08-17 |
| EP0479384A1 (de) | 1992-04-08 |
| CA2052560C (en) | 2002-04-09 |
| RO109843B1 (ro) | 1995-06-30 |
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