DE3808817A1 - Verfahren zur herstellung von metallisierbaren monoazofarbstoffen - Google Patents
Verfahren zur herstellung von metallisierbaren monoazofarbstoffenInfo
- Publication number
- DE3808817A1 DE3808817A1 DE3808817A DE3808817A DE3808817A1 DE 3808817 A1 DE3808817 A1 DE 3808817A1 DE 3808817 A DE3808817 A DE 3808817A DE 3808817 A DE3808817 A DE 3808817A DE 3808817 A1 DE3808817 A1 DE 3808817A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- pyridine
- coupling
- formula
- nitrophenol
- 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.)
- Withdrawn
Links
- 239000000975 dye Substances 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 123
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 62
- 238000005859 coupling reaction Methods 0.000 claims abstract description 52
- 230000008878 coupling Effects 0.000 claims abstract description 45
- 238000010168 coupling process Methods 0.000 claims abstract description 45
- 239000000987 azo dye Substances 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 11
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 amino, phenylamino Chemical group 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims abstract description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 3
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 3
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 3
- 210000002268 wool Anatomy 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 34
- 238000001256 steam distillation Methods 0.000 claims description 10
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 claims description 5
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-UHFFFAOYSA-N 0.000 claims description 5
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 claims description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 4
- HGWQOFDAUWCQDA-UHFFFAOYSA-N 4-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 HGWQOFDAUWCQDA-UHFFFAOYSA-N 0.000 claims description 4
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 claims description 4
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims description 3
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 claims description 3
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 claims description 2
- MHAFRUMLQZZSIN-UHFFFAOYSA-N 2-amino-4-chloro-6-nitrophenol Chemical compound NC1=CC(Cl)=CC([N+]([O-])=O)=C1O MHAFRUMLQZZSIN-UHFFFAOYSA-N 0.000 claims description 2
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 claims description 2
- DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 claims description 2
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-UHFFFAOYSA-N 0.000 claims description 2
- FQVOHUNTVPFJNU-UHFFFAOYSA-N 7-acetamido-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=C(O)C=C(S(O)(=O)=O)C2=CC(NC(=O)C)=CC=C21 FQVOHUNTVPFJNU-UHFFFAOYSA-N 0.000 claims description 2
- 229950011260 betanaphthol Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000004532 chromating Methods 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract description 2
- 238000006193 diazotization reaction Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- MUCCHGOWMZTLHK-UHFFFAOYSA-N 2-nitronaphthalen-1-ol Chemical group C1=CC=C2C(O)=C([N+]([O-])=O)C=CC2=C1 MUCCHGOWMZTLHK-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical class ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229910006074 SO2NH2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- 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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/004—Special methods of performing the coupling reaction characterised by the coupling medium containing a reaction assistant, e.g. urea
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1051/87A CH677303B5 (enrdf_load_stackoverflow) | 1987-03-19 | 1987-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3808817A1 true DE3808817A1 (de) | 1988-09-29 |
Family
ID=4201306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3808817A Withdrawn DE3808817A1 (de) | 1987-03-19 | 1988-03-16 | Verfahren zur herstellung von metallisierbaren monoazofarbstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE1000630A5 (enrdf_load_stackoverflow) |
| CH (1) | CH677303B5 (enrdf_load_stackoverflow) |
| DE (1) | DE3808817A1 (enrdf_load_stackoverflow) |
| ES (1) | ES2009571A6 (enrdf_load_stackoverflow) |
| FR (1) | FR2612523B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2202232B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994561A (en) * | 1987-12-07 | 1991-02-19 | Ciba-Geigy Corporation | Process for the preparation of metallizable azo dyes carrying out coupling in an inert gas atmosphere in the presence of an ammonium salt |
| US5003051A (en) * | 1988-08-24 | 1991-03-26 | Ciba-Geigy Corporation | Process for the preparation of metallizable monoazo dyes in the presence of ketones |
| US5026830A (en) * | 1987-09-08 | 1991-06-25 | Ciba-Geigy Corporation | Process for the preparation of azo dyes by carrying out coupling in the presence of an alkali metal chloride and ammonium chloride |
| US5126435A (en) * | 1987-12-07 | 1992-06-30 | Ciba-Geigy Corporation | Process for the preparation of metallisable azo dyes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101908869B1 (ko) * | 2017-12-26 | 2018-10-16 | (주)바이오액츠 | 마그네슘 이온의 검출을 통하여 메티실린 내성 황색포도상구균(mrsa)의 감염을 진단하기 위한 키트 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD294394A7 (de) * | 1987-03-16 | 1991-10-02 | Chemie Ag Bitterfeld-Wolfen,De | Verfahren zur herstellung von mono-, dis-,tretakis- und pentakisazofarbstoffen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR760996A (fr) * | 1932-10-14 | 1934-03-07 | Ste Ind Chim Bale | Matières colorantes dis- & polyazoïques |
| CH181716A (de) * | 1934-11-05 | 1935-12-31 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Azofarbstoffes. |
| CH178818A (de) * | 1935-07-24 | 1935-08-15 | Geigy Ag J R | Verfahren zur Herstellung eines neuen Azofarbstoffes. |
| DE842986C (de) * | 1946-04-11 | 1952-07-03 | Ciba Geigy | Verfahren zur Herstellung von sulfonsaeuregruppenfreien Disazofarbstoffen |
| GB768236A (en) * | 1952-10-15 | 1957-02-13 | Ciba Ltd | Metalliferous monoazo-dyestuffs and process for making them |
| GB751974A (en) * | 1953-02-04 | 1956-07-04 | Geigy Ag J R | Improvements relating to metallisable monoazo dyestuffs and dyeings made therewith |
| GB820158A (en) * | 1955-12-23 | 1959-09-16 | Sandoz Ltd | Improvements in or relating to metalliferous mono-azo dyestuffs of the benzene azo-naphthalene series |
| GB853998A (en) * | 1957-03-29 | 1960-11-16 | Geigy Ag J R | Improvements relating to chromium-containing benzene-monoazo-naphthalene dyestuffs and their use |
| NL108334C (enrdf_load_stackoverflow) * | 1957-11-15 | |||
| CH386025A (de) * | 1958-10-21 | 1964-12-31 | Geigy Ag J R | Verfahren zur Herstellung von reaktiven Farbstoffen |
-
1987
- 1987-03-19 CH CH1051/87A patent/CH677303B5/de unknown
-
1988
- 1988-03-16 FR FR888803403A patent/FR2612523B1/fr not_active Expired
- 1988-03-16 GB GB8806245A patent/GB2202232B/en not_active Expired - Lifetime
- 1988-03-16 DE DE3808817A patent/DE3808817A1/de not_active Withdrawn
- 1988-03-18 ES ES8800834A patent/ES2009571A6/es not_active Expired
- 1988-03-18 BE BE8800313A patent/BE1000630A5/fr not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD294394A7 (de) * | 1987-03-16 | 1991-10-02 | Chemie Ag Bitterfeld-Wolfen,De | Verfahren zur herstellung von mono-, dis-,tretakis- und pentakisazofarbstoffen |
Non-Patent Citations (2)
| Title |
|---|
| H.Zollinger in Chemie der Azofarbstoffe BirkhäuserVerlag Basel und Stuttgart, S.158ff, 1958 * |
| R.Pütter in Angew. Chem. 63,8, S.188-192,(1951) * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5026830A (en) * | 1987-09-08 | 1991-06-25 | Ciba-Geigy Corporation | Process for the preparation of azo dyes by carrying out coupling in the presence of an alkali metal chloride and ammonium chloride |
| US5196518A (en) * | 1987-09-08 | 1993-03-23 | Ciba-Geigy Corporation | Process for the preparation of metallizable azo dyes by carrying out the coupling in the presence of a buffer mixture |
| US4994561A (en) * | 1987-12-07 | 1991-02-19 | Ciba-Geigy Corporation | Process for the preparation of metallizable azo dyes carrying out coupling in an inert gas atmosphere in the presence of an ammonium salt |
| US5126435A (en) * | 1987-12-07 | 1992-06-30 | Ciba-Geigy Corporation | Process for the preparation of metallisable azo dyes |
| US5003051A (en) * | 1988-08-24 | 1991-03-26 | Ciba-Geigy Corporation | Process for the preparation of metallizable monoazo dyes in the presence of ketones |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2202232B (en) | 1991-03-06 |
| GB2202232A (en) | 1988-09-21 |
| CH677303B5 (enrdf_load_stackoverflow) | 1991-11-15 |
| CH677303GA3 (enrdf_load_stackoverflow) | 1991-05-15 |
| FR2612523B1 (fr) | 1989-10-06 |
| BE1000630A5 (fr) | 1989-02-21 |
| ES2009571A6 (es) | 1989-10-01 |
| FR2612523A1 (fr) | 1988-09-23 |
| GB8806245D0 (en) | 1988-04-13 |
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