DE3917113C2 - - Google Patents
Info
- Publication number
- DE3917113C2 DE3917113C2 DE3917113A DE3917113A DE3917113C2 DE 3917113 C2 DE3917113 C2 DE 3917113C2 DE 3917113 A DE3917113 A DE 3917113A DE 3917113 A DE3917113 A DE 3917113A DE 3917113 C2 DE3917113 C2 DE 3917113C2
- Authority
- DE
- Germany
- Prior art keywords
- diamino
- general formula
- nitrobenzene
- stage
- yield
- Prior art date
- 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
Links
- -1 chloroformate chloroalkyl ester Chemical class 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 12
- HVHNMNGARPCGGD-UHFFFAOYSA-N 2-nitro-p-phenylenediamine Chemical class NC1=CC=C(N)C([N+]([O-])=O)=C1 HVHNMNGARPCGGD-UHFFFAOYSA-N 0.000 claims description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 6
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003254 radicals Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 238000005580 one pot reaction Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- SVDDJQGVOFZBNX-UHFFFAOYSA-N 2-chloroethyl carbonochloridate Chemical compound ClCCOC(Cl)=O SVDDJQGVOFZBNX-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 6
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 6
- MTXMEFUEBCFWCY-UHFFFAOYSA-N 3-chloropropyl carbonochloridate Chemical compound ClCCCOC(Cl)=O MTXMEFUEBCFWCY-UHFFFAOYSA-N 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- PJRDJHIRYREDHP-UHFFFAOYSA-N 2-methyl-5-nitrobenzene-1,4-diamine Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1N PJRDJHIRYREDHP-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- VUNAQOGRLGNALG-UHFFFAOYSA-N 2-chloro-5-nitrobenzene-1,4-diamine Chemical compound NC1=CC([N+]([O-])=O)=C(N)C=C1Cl VUNAQOGRLGNALG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- JFRMKFCHDCINEO-UHFFFAOYSA-N 2-ethoxy-5-nitrobenzene-1,4-diamine Chemical compound CCOC1=CC(N)=C([N+]([O-])=O)C=C1N JFRMKFCHDCINEO-UHFFFAOYSA-N 0.000 description 2
- YXHNYYAGVDNJIK-UHFFFAOYSA-N 2-methoxy-5-nitrobenzene-1,4-diamine Chemical compound COC1=CC(N)=C([N+]([O-])=O)C=C1N YXHNYYAGVDNJIK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- HSGBFZPVFUDWGR-UHFFFAOYSA-N 2-fluoro-5-nitrobenzene-1,4-diamine Chemical compound NC1=CC([N+]([O-])=O)=C(N)C=C1F HSGBFZPVFUDWGR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000118 hair dye Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- ZRBJEBJVJJPIDF-UHFFFAOYSA-N methyl n-(4-amino-3-nitrophenyl)carbamate Chemical compound COC(=O)NC1=CC=C(N)C([N+]([O-])=O)=C1 ZRBJEBJVJJPIDF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/418—Amines containing nitro groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3917113A DE3917113A1 (de) | 1989-05-26 | 1989-05-26 | Verfahren zur selektiven herstellung von n(pfeil hoch)4(pfeil hoch)-substituierten 1,4-diamino-2-nitrobenzolen |
| US07/518,710 US5091581A (en) | 1989-05-26 | 1990-05-07 | Process for the selective preparation of n-substituted 1,4-diamino-2-nitrobenzenes |
| JP2132764A JPH0317045A (ja) | 1989-05-26 | 1990-05-24 | Ｎ↓４―置換ジアミノ―２―ニトロベンゾールの選択的製造方法及びｎ↓４―置換１，４―ジアミノ―２―ニトロベンゾール |
| GB9011760A GB2232419B (en) | 1989-05-26 | 1990-05-25 | Process for selective preparation of n4-substituted 1,4-diamino-2-nitrobenzenes |
| FR909006577A FR2647446B1 (fr) | 1989-05-26 | 1990-05-28 | Procede pour la preparation selective de 1,4-diamino-2-nitrobenzenes substitues en n4 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3917113A DE3917113A1 (de) | 1989-05-26 | 1989-05-26 | Verfahren zur selektiven herstellung von n(pfeil hoch)4(pfeil hoch)-substituierten 1,4-diamino-2-nitrobenzolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3917113A1 DE3917113A1 (de) | 1990-11-29 |
| DE3917113C2 true DE3917113C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-02 |
Family
ID=6381416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3917113A Granted DE3917113A1 (de) | 1989-05-26 | 1989-05-26 | Verfahren zur selektiven herstellung von n(pfeil hoch)4(pfeil hoch)-substituierten 1,4-diamino-2-nitrobenzolen |
Country Status (5)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3917114C3 (de) * | 1989-05-26 | 1996-08-14 | Schwarzkopf Gmbh Hans | Neue Nitro-p-phenylendiaminderivate, Verfahren zu ihrer Herstellung sowie Färbemittel für keratinische Fasern, die diese enthalten |
| DE4142132C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1991-12-20 | 1993-05-27 | Cassella Ag, 6000 Frankfurt, De | |
| DE4200259A1 (de) * | 1992-01-08 | 1993-07-15 | Asta Medica Ag | Neue 1,2,4-triaminobenzol-derivate und verfahren zu deren herstellung |
| DE4329727C2 (de) * | 1993-09-03 | 1997-05-15 | Hoechst Ag | Verfahren zur Herstellung von Hydroxyalkylaminonitrobenzol-Derivaten |
| CA2148535A1 (en) * | 1994-06-24 | 1995-12-25 | Mu-Ill Lim | 5-mercapto-2-nitro paraphenylenediamine compounds and hair dye compositions containing same |
| DE19701694A1 (de) * | 1997-01-20 | 1998-07-23 | Asta Medica Ag | Neue Modifikationen des 2-Amino-4-(4-fluorbenzylamino)-l-ethoxycarbonyl-aminobenzen sowie Verfahren zu ihrer Herstellung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE672401A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1964-11-19 | 1966-05-16 | ||
| GB1228604A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-11-05 | 1971-04-15 | ||
| US4005217A (en) * | 1970-06-26 | 1977-01-25 | May & Baker Limited | Treatment of helminth infections with substituted phenyl-thiourea derivatives |
| LU74807A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-04-21 | 1977-12-02 | ||
| LU82860A1 (fr) * | 1980-10-16 | 1982-05-10 | Oreal | Compositions tinctoriales a base de precurseurs de colorants d'oxydation et de colorants nitres benzeniques stables en milieu alcalin reducteur et leur utilisation pour la teinture des fibres keratiniques |
| GB2086408B (en) * | 1980-10-16 | 1985-10-09 | Oreal | New nitro-derivatives of the benzene series the process for their preparation and their use in the dyeing of keratin fibres |
| DE3302817A1 (de) * | 1983-01-28 | 1984-08-02 | Hans Schwarzkopf Gmbh, 2000 Hamburg | Substituierte 4-amino-3-nitrophenole, verfahren zu ihrer herstellung sowie haarfaerbemittel, die diese enthalten |
| FR2569401B1 (fr) * | 1984-08-23 | 1989-01-20 | Oreal | Nouveaux derives dimethyles de nitro-3 amino-4 aniline, leur procede de preparation et leur utilisation en teinture des fibres keratiniques |
| FR2571364B1 (fr) * | 1984-10-09 | 1987-07-17 | Oreal | Nouveau procede de preparation de nitroparaphenylenediamines n,n'-disubstituees, nouvelles oxazolidones utilisees dans ce procede, nouvelles nitroparaphenylenediamines n,n'-disubstituees obtenues selon ce procede et compositions tinctoriales contenant les nitroparaphenylenediamines n,n'-disubstituees obtenues selon ledit procede |
-
1989
- 1989-05-26 DE DE3917113A patent/DE3917113A1/de active Granted
-
1990
- 1990-05-07 US US07/518,710 patent/US5091581A/en not_active Expired - Fee Related
- 1990-05-24 JP JP2132764A patent/JPH0317045A/ja active Pending
- 1990-05-25 GB GB9011760A patent/GB2232419B/en not_active Expired - Fee Related
- 1990-05-28 FR FR909006577A patent/FR2647446B1/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2232419A (en) | 1990-12-12 |
| FR2647446A1 (fr) | 1990-11-30 |
| GB2232419B (en) | 1992-06-24 |
| GB9011760D0 (en) | 1990-07-18 |
| JPH0317045A (ja) | 1991-01-25 |
| US5091581A (en) | 1992-02-25 |
| FR2647446B1 (fr) | 1992-08-14 |
| DE3917113A1 (de) | 1990-11-29 |
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Legal Events
| Date | Code | Title | Description |
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| OP8 | Request for examination as to paragraph 44 patent law | ||
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