DE842982C - Process for the production of chromium-containing azo dyes - Google Patents
Process for the production of chromium-containing azo dyesInfo
- Publication number
- DE842982C DE842982C DEP35233A DEP0035233A DE842982C DE 842982 C DE842982 C DE 842982C DE P35233 A DEP35233 A DE P35233A DE P0035233 A DEP0035233 A DE P0035233A DE 842982 C DE842982 C DE 842982C
- Authority
- DE
- Germany
- Prior art keywords
- chromium
- azo dyes
- dyes
- containing azo
- production
- 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
Links
- 239000011651 chromium Substances 0.000 title claims description 12
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 10
- 229910052804 chromium Inorganic materials 0.000 title claims description 10
- 239000000987 azo dye Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 12
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 7
- 150000001845 chromium compounds Chemical class 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004755 animal textile Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur -Herstellung chromhaltiger Azofarbstoffe Es wurde gefunden, daß wertvolle chromhaltige Azofarbstoffe hergestellt werden können, wenn man o-Oxyazofarbstoffe der allgemeinen Formel worin R einen von Sulfonsäuregruppen freien Naphthalinrest bedeutet, der in r-Stellung die Azogruppe und .in 2-Stellung die Oxygruppe trägt und weiter substituiert sein kann, in Substanz mit chromabgebenden Mitteln behandelt.Process for the production of chromium-containing azo dyes It has been found that valuable chromium-containing azo dyes can be produced by using o-oxyazo dyes of the general formula where R denotes a naphthalene radical which is free of sulfonic acid groups and which carries the azo group in the r position and the oxy group in the 2 position and can be further substituted, treated in substance with chromium donating agents.
Die dem vorliegenden Verfahren als Ausgangsstoffe dienenden Azofarbstoffe können beispielsweise durch Vereinigen von diazotierter 2-Amino-z-oxybenzol-4, 6-disülfonsäure mit unsulfonierten, _ in i-Stellung kupplungsfähigen 2-Oxynaphthalinen erhalten werden. Diese 2-Oxynaphthaline können weitere Substituenten, vorzugsweise solche von nichtlöslichmachendem Charakter, aufweisen, z. B. Alkylgruppen, insbesondere solche der niederen aliphatischen Reihe, wie Äthyl-und Methylgruppen, Alkoxygruppen derselben Reihe, wie Äthoxy- und Methoxygruppen, hauptsächlich aber Halogene, insbesondere Brom und Chlor. Als Beispiele für Azokomponenten, die zur Herstellung der gemäß vorliegendem Verfahren verwendbaren Farbstoffe dienen können, seien die folgenden genannt: 2-Oxynaphthalin, 2-Oxy-6- 'bzw. -7-methoxynaphthalin, 2-Oxy-5, 8-dichlornaphthalin sowie 2-Oxy-5, 8-dibromnaphthalin. Die Kupplung der diazotierten 2-Aminoi-oxybenzo1-4, 6-disulfonsäure mit den 2-Oxynaph@ thalinen kann in üblicher Weise vorgenommen werden.The azo dyes used as starting materials for the present process can, for example, by combining diazotized 2-amino-z-oxybenzene-4, 6-disulfonic acid obtained with unsulfonated 2-oxynaphthalenes capable of coupling in the i-position will. These 2-oxynaphthalenes can have further substituents, preferably such of non-solubilizing character, have e.g. B. alkyl groups, in particular those of the lower aliphatic series, such as ethyl and methyl groups, alkoxy groups same series as ethoxy and methoxy groups, but mainly halogens, in particular Bromine and chlorine. As examples for azo components used in manufacture of the dyes which can be used in accordance with the present process are the called the following: 2-oxynaphthalene, 2-oxy-6- 'or -7-methoxynaphthalene, 2-oxy-5, 8-dichloronaphthalene and 2-oxy-5, 8-dibromonaphthalene. The coupling of the diazotized 2-Aminoi-oxybenzo1-4, 6-disulfonic acid with the 2-Oxynaph @ thalines can be used in the usual Way to be made.
Als chromabgebende Mittel, mit denen die öbenerwähnten Farbstoffe behandelt werden sollen, 'kom. men gemäß vorliegendem Verfahren praktisch alle Chromverbindungen in Betracht, die üblicherweise zur Überführung von Azofarbstoffen in komplexe Chromverbindungen verwendet werden, so insbesondere Salze des 3wertigen Chroms, wie das Acetat, das Fluorid und insbesondere das Sulfat. Die Behandlung kann vorzugsweise in wässerigem Medium in Gegenwart oder Abwesenheit organischer Lösungsmittel, wie Alkohol oder Pyridin, in neutralem oder alkalischem Medium, gegebenenfalls unter Mitverwendung komplexbildender Substanzen, wie aliphatischer oder aromatischer Oxycarbonsäuren, gewünschtenfalls unter Zusatz @ von anorganischen oder organischen Salzen, offen oder unter Druck erfolgen. In vielen Fällen ist es zweckmäßig, auf i Mol des Farbstoffs i Atom Chrom bzw. einen gewissen Überschuß zu verwenden.As a chromium donating agent with which the aforementioned dyes should be treated, 'kom. men according to the present process practically all chromium compounds into consideration, which is usually used to convert azo dyes into complex chromium compounds are used, so in particular salts of trivalent chromium, such as the acetate, the Fluoride and especially the sulfate. The treatment can preferably be in aqueous Medium in the presence or absence of organic solvents, such as alcohol or Pyridine, in a neutral or alkaline medium, optionally with use as well complex-forming substances, such as aliphatic or aromatic oxycarboxylic acids, if desired with the addition of inorganic or organic salts, open or under pressure. In many cases it is useful to use one mole of the dye i atom of chromium or a certain excess should be used.
Die nach dem vorliegenden Verfahren erhältlichen komplexen Chromverbindungen der verwendeten Azofarbstoffe eignen sich zum Färben verschiedener Materialien, insbesondere tierischer Natur, wie Ca$ein, Gelatine, und hauptsächlich zum Färben und Bedrucken tierischer Textilfasern, wie Wolle, Seide und Leder, sowie solcher Fasern, die sich färberisch ähnlich verhalten, wie Zellwolle aus Caseinfasern, animalisierte Cellulosekunstseide, gegebenenfalls auch zum Färben und Bedrucken von Kunstfasern aus Superpolyamiden u. dgl. (Nylon). Man erhält u. a. wertvolle blaue bis rotviolette Töne von guter Echtheit und Gleichmäßigkeit.The complex chromium compounds obtainable by the present process the azo dyes used are suitable for dyeing various materials, especially of animal nature, such as calcium, gelatin, and mainly for coloring and printing on animal textile fibers such as wool, silk and leather, as well as the like Fibers that behave in a similar way in terms of dyeing, such as rayon made from casein fibers, animalized Cellulose rayon, possibly also for dyeing and printing synthetic fibers made of super polyamides and the like (nylon). One obtains inter alia. valuable blue to red-violet Tones of good authenticity and evenness.
Die nachfolgenden Beispiele dienen zur Erläuterung der Erfindung, ohne diese jedoch irgendwie einzuschränken; dabei bedeuten dieTeile Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen sind in Celsiusgraden angegeben.The following examples serve to illustrate the invention, but without restricting them in any way; the parts mean parts by weight and the percentages are percentages by weight. The temperatures are given in degrees Celsius.
Beispiel i 46,8 Teile Dinatriumsalz des Farbstoffes aus diazotierter 2-Amino-i-oxybenzol-4, 6-disulfonsäure und 2-Oxynaphthalin werden mit 5oo Teilen Wasser .und ioo Teilen einer Chromsulfatlösung, deren Chromgehalt 8,4 Teile Cr,03 entspricht, längere Zeit unter Rückflußkühlung zum Sieden erhitzt. Die erhaltene rotviolett gefärbte Chromverbindung des Farbst<es läßt sich nach erfolgtem Neutralisieren der Lb4ung durch Eindampfen im Vakuum gewinnen. Die zur Trockne eingedampfte Chromverbindung stellt ein violettschwarz gefärbtes Pulver dar, das sich in Wasser und verdünnter Natriumcarbonatlösung mit rotvioletter und in konzentrierter Schwefelsäure mit violettblauer Farbe löst. Der Farbstoff färbt Wolle aus schwefelsaurem Bade in sehr gleichmäßigen, lichtechw rotvioletten Tönen.Example i 46.8 parts of the disodium salt of the dye from diazotized 2-Amino-i-oxybenzene-4, 6-disulfonic acid and 2-oxynaphthalene are 500 parts Water and 100 parts of a chromium sulfate solution, the chromium content of which is 8.4 parts of Cr, 03 corresponds, heated to boiling under reflux for a long time. The received The chromium compound of the dye is red-violet and can be neutralized after it has been neutralized Obtain the solution by evaporation in vacuo. The chromium compound evaporated to dryness represents a purple-black colored powder that dissolves in water and dilutes Sodium carbonate solution with red-violet and in concentrated sulfuric acid with violet-blue Color dissolves. The dye dyes wool from sulfuric acid bath in very even, light blue red-violet tones.
Beispiel 2 26,9 Teile 2-Amino-i-oxybenzol-4, 6-disulfonsäure werden in üblicher Weise diazotiert, und die Diazoverbindung wird in alkalischer Lösung mit 22 Teilen 5, 8-Dichlor-2-öxynaphthalin gekuppelt. Der durch Zusatz von Natriumchlorid abgeschiedene und ab-'filtrierte Fgrbefbl wird mit goo Teilen Wasser und ioo Teilen einer :' Chrbmsulfatlösung, deren Chromgehalt 8,4 Teilen Cr, 0, entspricht, längere Zeit unter Rückflußkühlung zum Sieden erhitzt. Die erhaltene rotviolett gefärbte Chromverbindung des Farbstoffes läßt sich durch Zusatz von Natriumchlorid abscheiden. Die abfiltrierte und getrocknete Chromverbindung stellt ein violettes Pulver dar, das sich in Wasser und verdünnter Natriumcarbonatlösung mit rotvioletter und in konzentrierter Schwefelsäure mit blauer Farbe löst. Der Farbstoff färbt Wolle aus schwefelsaurem Bade in reinen sehr' gleichmäßigen rotvioletten Tönen; die sich durch sehr gute Echtheitseigenschaften auszeichnen.Example 2 26.9 parts of 2-amino-i-oxybenzene-4, 6-disulfonic acid are diazotized in the customary manner, and the diazo compound is coupled in alkaline solution with 22 parts of 5, 8-dichloro-2-oxynaphthalene. The Fgrbefbl separated by the addition of sodium chloride and filtered off is heated to boiling for a long time under reflux cooling with 100 parts of water and 100 parts of a chromium sulfate solution, the chromium content of which corresponds to 8.4 parts of Cr, 0. The resulting red-violet colored chromium compound of the dye can be separated off by adding sodium chloride. The filtered and dried chromium compound is a violet powder that dissolves in water and dilute sodium carbonate solution with red-violet and in concentrated sulfuric acid with blue color. The dye dyes wool from a sulfuric acid bath in pure, very even red-violet shades; which are characterized by very good fastness properties.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH842982X | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE842982C true DE842982C (en) | 1952-07-03 |
Family
ID=4541478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP35233A Expired DE842982C (en) | 1946-10-08 | 1949-02-27 | Process for the production of chromium-containing azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE842982C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1205212B (en) * | 1959-01-17 | 1965-11-18 | Bayer Ag | Process for the production of metal-containing azo dyes |
-
1949
- 1949-02-27 DE DEP35233A patent/DE842982C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1205212B (en) * | 1959-01-17 | 1965-11-18 | Bayer Ag | Process for the production of metal-containing azo dyes |
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