DE1210962C2 - Process for the production of metal-containing, water-insoluble azo dyes - Google Patents
Process for the production of metal-containing, water-insoluble azo dyesInfo
- Publication number
- DE1210962C2 DE1210962C2 DE1961F0032946 DEF0032946A DE1210962C2 DE 1210962 C2 DE1210962 C2 DE 1210962C2 DE 1961F0032946 DE1961F0032946 DE 1961F0032946 DE F0032946 A DEF0032946 A DE F0032946A DE 1210962 C2 DE1210962 C2 DE 1210962C2
- Authority
- DE
- Germany
- Prior art keywords
- black
- azo
- amino
- oxynaphthoylamino
- methyl
- 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
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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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/28—Tetrazo dyes of the type A->B->K<-C<-D
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/10—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes containing metal
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
- D06P1/12—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes prepared in situ
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
Int. σ.:Int. σ .:
Nummer:Number:
Aktenzeichen:File number:
Anmeldetag:Registration date:
Auslegetag:Display day:
Ausgabetag:Issue date:
C09bC09b
Deutsche Kl.: 22 a-5German class: 22 a-5
1210 962
F32946IVc/22a
12. Januar 1961
17. Februar 1966
15. September 19661210 962
F32946IVc / 22a
January 12, 1961
17th February 1966
September 15, 1966
Patentschrift stimmt mit der Auslegeschrift übereinThe patent specification corresponds to the patent specification
Es wurde gefunden, daß man zu neuen metallhaltigen, wasserunlöslichen Azofarbstoffen gelangt, wenn man die Diazoniumverbindungen von Aminen der allgemeinen FormelIt has been found that new metal-containing, water-insoluble azo dyes, if you take the diazonium compounds of amines of the general formula
R»R »
A-N = N-A-N = N-
V- NH2 NHV-NH 2 NH
Ri R i
worin A einen aromatischen oder heterocyclischen Rest, R1 ein Wasserstoffatom oder eine Alkylgruppe und R2 sowie R3 ein Wasserstoffatom, eine Alkyl- oder Alkoxygruppe bedeuten, mit Arylamiden von aromatischen oder heterocyclischen o-Oxycarbonsäuren oder von Acylessigsäuren in Substanz, auf der Faser oder auf einem anderen Substrat kuppelt, wobei man die Komponenten so wählt, daß sie keine wasserlöslichmachenden Gruppen, wie Sulfonsäure- oder Carbonsäuregruppen, enthalten, und die so erhaltenen Farbstoffe mit metallabgebenden Mitteln behandelt.where A is an aromatic or heterocyclic radical, R 1 is a hydrogen atom or an alkyl group and R 2 and R 3 are a hydrogen atom, an alkyl or alkoxy group, with arylamides of aromatic or heterocyclic o-oxycarboxylic acids or of acyl acetic acids in substance, on the fiber or on another substrate, the components being chosen so that they do not contain any water-solubilizing groups, such as sulfonic acid or carboxylic acid groups, and the dyes thus obtained are treated with metal donating agents.
Die Behandlung der erfindungsgemäß erhältlichen wasserunlöslichen Azofarbstoffe mit den metallabgebenden Mitteln kann während oder nach der Kupplung in Substanz oder auf der Faser in bekannter Weise erfolgen. Die Behandlung mit den metallabgebenden Mitteln nach der Kupplung wird vorzugsweise in neutralem, schwach saurem oder schwach alkalischem Medium vorgenommen. Bei der Herstellung der Farbstoffe auf der Faser kann man so verfahren, daß man die Metallisierung durch Zugabe der metallabgebenden Verbindung zum Entwicklungsbad vornimmt oder diese Verbindungen bereits dem Grundierungsbad zugibt. Die Behandlung der Farbstoffe mit den metallabgebenden Mitteln nach der Kupplung kann in einem zweiten Bad erfolgen, das neutral, schwach alkalisch oder schwach sauer gehalten ist und das gegebenenfalls Dispergier- oder Waschmittel, beispielsweise Fettalkoholpolyglykoläther, Alkylphenolpolyglykoläther, Alkylnaphtholpolyglykoläther, Fettsäurepolyglykolester oder Fettsäureamidpolyglykoläther, enthält. ·The treatment of the water-insoluble azo dyes obtainable according to the invention with the metal donating ones Agents can be known during or after the coupling in bulk or on the fiber Way to be done. Post-coupling treatment with the metal donors is preferred made in neutral, weakly acidic or weakly alkaline medium. In the preparation of the dyes on the fiber can be done by adding the metallization the metal-releasing compound to the development bath or these compounds already the Adding primer bath. Treatment of dyes with metal donors after Coupling can take place in a second bath, which is kept neutral, weakly alkaline or weakly acidic and the optionally dispersing or detergent, for example fatty alcohol polyglycol ether, alkylphenol polyglycol ether, Alkyl naphthol polyglycol ethers, fatty acid polyglycol esters or fatty acid amide polyglycol ethers, contains. ·
Als metallabgebende Mittel kommen bei dem erfindungsgemäßen Verfahren vorwiegend kupfer-, kobalt-,
nickel-, eisen- und zinkabgebende Verbindungen in Betracht, die in Form ihrer anorganischen oder organischen
Salze, beispielsweise als Chloride, Bromide, Verfahren zur Herstellung von metallhaltigen,
wasserunlöslichen AzofarbstoffenAs metal donors in the process according to the invention, mainly copper, cobalt, nickel, iron and zinc donating compounds come into consideration, which in the form of their inorganic or organic salts, for example as chlorides, bromides, processes for the production of metal-containing,
water-insoluble azo dyes
Patentiert für:Patented for:
Farbwerke Hoechst Aktiengesellschaft
vormals Meister Lucius & Brüning,
Frankfurt/M.Farbwerke Hoechst Aktiengesellschaft
formerly Master Lucius & Brüning,
Frankfurt / M.
Als Erfinder benannt:Named as inventor:
Dr. Hasso Hertel,Dr. Hasso Hertel,
Dr. Reinhard Mohr,Dr. Reinhard Mohr,
Dr. Walter Staab, Offenbach/M.Dr. Walter Staab, Offenbach / M.
Sulfate, Nitrate, Formiate oder Acetate, oder als Komplexverbindungen, insbesondere mit Oxyalkylaminen, beispielweise Diäthanolamin, Triäthanolamin oder N-Methyläthanolamin, mit Aminosäuren, beispielsweise mit Aminoessigsäure oder Nitrilotriessigsäure, mit aliphatischen Oxycarbonsäuren, beispielsweise Weinsäure, Zitronensäure oder Gluconsäure, oder mit Alkaliphosphaten, beispielsweise Alkalipolyphosphaten oder Alkalipyrophosphaten, zur Anwendung gelangen können. Bei der Verwendung eines kobaltabgebenden Mittels wirkt sich ein Zusatz von Oxydationsmitteln, wie beispielsweise Alkaliperboraten, Alkalipercarbonaten oder Verbindungen des 6wertigen Chroms, günstig auf die Metallisierung aus. Auf pflanzlichen Fasern, einschließlich solchen aus regenerierter Cellulose, erhält man nach den aus der Eisfarbentechnik bekannten Färbe- und Druckverfahren Farbstoffe, die sich neben guten Allgemeinechtheiten insbesondere durch sehr gute Lichtechtheiten auszeichnen.Sulfates, nitrates, formates or acetates, or as complex compounds, in particular with oxyalkylamines, for example diethanolamine, triethanolamine or N-methylethanolamine, with amino acids, for example with aminoacetic acid or nitrilotriacetic acid, with aliphatic oxycarboxylic acids, for example Tartaric acid, citric acid or gluconic acid, or with alkali phosphates, for example alkali polyphosphates or alkali pyrophosphates, can be used. When using a cobalt-releasing agent, the addition of oxidizing agents, such as alkali perborates, has an effect Alkali percarbonates or compounds of hexavalent chromium are beneficial for metallization. On vegetable fibers, including those made from regenerated cellulose, according to the Ice color technology known dyeing and printing process dyes, which in addition to good general fastness properties characterized in particular by very good lightfastness.
Die Herstellung der Farbstoffe auf pflanzlichen Fasern kann in langen Flotten erfolgen. Stückware, Ketten und Bänder können ferner in kontinuierlicher Weise gefärbt oder nach den Methoden des Basen- oder Naphtholataufdruckes bedruckt werden.The production of the dyes on vegetable fibers can take place in long liquors. Piece goods, Chains and ribbons can also be colored in a continuous manner or by the methods of the base or Naphtholate imprint can be printed.
Die neuen Farbstoffe können auch auf tierischen Fasern, wie Wolle oder Seide, sowie auf synthetischen Fasern, wie Polyamid-, Acetylcellulose- oder PoIyvinylalkoholfasern, nach den bei diesen Fasern üblichen Färbeverfahren hergestellt werden.The new dyes can also be used on animal fibers, such as wool or silk, as well as on synthetic ones Fibers such as polyamide, acetyl cellulose or polyvinyl alcohol fibers, can be produced using the dyeing processes customary for these fibers.
Die Farbstoffe lassen sich ferner in Substanz herstellen und durch Behandeln mit metallabgebenden Mitteln in die komplexen Metallverbindungen über-The dyes can also be produced in bulk and by treatment with metal donors Agents in the complex metal compounds
609 673/256609 673/256
führen. Die so erhältlichen Metallkomplexverbindungen eignen sich zum Färben von synthetischen Fasern sowie von hochmolekularen organischen plastischen Massen.to lead. The metal complex compounds obtainable in this way are suitable for dyeing synthetic fibers as well as high molecular weight organic plastic masses.
Als Azokomponenten können bei dem erfindungsgemäßen Verfahren Arylamide von aromatischen oder heterocyclischen o-Oxycarbonsäuren oder von Acylessigsäuren, beispielsweise der 2,3-Oxynaphthoesäure oder deren in 6-Stellung substituierten Derivate, ferner der 2-Oxyanthracen-3-carbonsäure, der 3-Oxydiphenylenoxyd-2-carbonsäure, der 2-Oxycarbazol-3-carbonsäure, der S-Oxy-l^l'^VbenzocarbazoM-carbonsäure, der Acetylessigsäure, der Benzoylessigsäure oder der Terephthaloyl-bis-essigsäure, verwendet" werden.Arylamides of aromatic or aromatic compounds can be used as azo components in the process according to the invention heterocyclic o-oxycarboxylic acids or acyl acetic acids, for example 2,3-oxynaphthoic acid or its derivatives substituted in the 6-position, furthermore of 2-oxyanthracene-3-carboxylic acid, of 3-oxydiphenylene oxide-2-carboxylic acid, of 2-oxycarbazole-3-carboxylic acid, of S-oxy-l ^ l '^ VbenzocarbazoM-carboxylic acid, acetylacetic acid, benzoylacetic acid or terephthaloyl-bis-acetic acid "can be used.
Als Aminoverbindungen, die der oben angegebenen Formel entsprechen und bei dem vorliegenden Verfahren vorteilhaft verwendet werden können, kommen Verbindungen in Betracht, in denen der aromatische oder heterocyclische Rest A durch nicht wasserlöslichmachende Gruppen, beispielsweise Halogenatome, Alkyl-, Alkoxy-, Aryloxy-, Trifluormethyl-, Nitro-, Alkylsulfon-, Arylsulfon-, Acyl-, Acylamino-, gegebenenfalls substituierte Sulfonsäureamid- oder Carbonsäureamide Cyan-, Arylazo- oder Dialkylaminogruppen substituiert sein können. Die Herstellung dieser Verbindungen kann zum Beispiel in bekannter Weise so erfolgen, daß man die Diazoniumverbindungen aus aromatischen oder heterocyclischen Aminen mit 7-Aminobenzimidazolen der allgemeinen FormelAs amino compounds corresponding to the formula given above and in the present process can be used advantageously, compounds in which the aromatic or heterocyclic radical A by groups that do not make water soluble, for example halogen atoms, Alkyl, alkoxy, aryloxy, trifluoromethyl, nitro, alkyl sulfone, aryl sulfone, acyl, acylamino, optionally substituted sulfonic acid amide or carboxylic acid amide cyano, arylazo or dialkylamino groups can be substituted. These compounds can be prepared, for example, in a known manner done so that the diazonium compounds from aromatic or heterocyclic amines with 7-aminobenzimidazoles of the general formula
R3 R2 R 3 R 2
NH,NH,
33%ig. gelöst. Die so erhaltene Lösung wird mit Wasser von 350C, das 3 g eines Kondensationsproduktes aus höhermolekularen Fettsäuren und Eiweißabbauprodukten und 10 ecm Natronlauge von38°Be enthält, auf 11 eingestellt.33%. solved. The solution thus obtained is diluted with water of 35 0 C, the 3 g of a condensation product of higher molecular weight fatty acids and protein degradation products, and 10 cc of sodium hydroxide solution contains von38 ° Be, adjusted to. 11
EntwicklungsbadDeveloping bath
2,7 g 7-Amino-5-methyl-4-(3'-methylphenyl-l'-azo)-benzimidazol werden mit 6 ecm Salzsäure von 20° Be2.7 g of 7-amino-5-methyl-4- (3'-methylphenyl-l'-azo) benzimidazole are mixed with 6 ecm of hydrochloric acid at 20 ° Be
ίο und 4 ecm Natriumnitritlösung 1: 5 diazotiert und die so erhaltene Diazolösung in ein Bad gegeben, das im Liter Wasser 2 g eines Einwirkungsproduktes von etwa 20 Mol Äthylenoxyd auf 1 Mol Octadecylalkohol, 20 g Natriumacetat und 2,8 g Nickelsulfat enthält. Man erhält eine Schwarzfärbung von guten Licht- und Naßechtheiten.ίο and 4 ecm sodium nitrite solution 1: 5 diazotized and the thus obtained diazo solution placed in a bath containing 2 g of an action product of in liter of water contains about 20 moles of ethylene oxide to 1 mole of octadecyl alcohol, 20 g of sodium acetate and 2.8 g of nickel sulfate. A black dyeing with good light and wet fastness properties is obtained.
Baumwollgarn wird im Flottenverhältnis 1:20 45 Minuten bei 350C im nachstehend beschriebenen Grundierungsbad behandelt, abgeschleudert und 30 Minuten bei 2O0C in dem nachstehend beschriebenen Entwicklungsbad entwickelt. Dann wird gespült und wie folgt metallisiert:Cotton yarn is treated at a liquor ratio of 1:20 for 45 minutes at 35 0 C in the below-described Grundierungsbad, spun down and developed for 30 minutes at 2O 0 C in the development bath described below. Then it is rinsed and metallized as follows:
2,8 g Nickelsulfat, gelöst in 28 ecm Wasser, werden mit 30 ecm einer Lösung von Aminoessigsäure in Wasser (1: 10) gemischt und mit 1 g eines Einwirkungsproduktes von etwa 10 Mol Äthylenoxyd auf 1 Mol Nonylphenol, 3 g Soda und Wasser auf 11 aufgefüllt. In dieser Lösung wird das gefärbte Material im Flottenverhältnis 1: 20 nachbehandelt, indem man von 60 auf 95°C erwärmt und 30 Minuten bei 95 0C behandelt. Anschließend wird 15 Minuten bei 950C mit 1 g eines Einwirkungsproduktes von etwa 10 Mol Äthylenoxyd auf 1 Mol Nonylphenol und 3 g Soda im Liter Wasser geseift, gespült und getrocknet.2.8 g of nickel sulfate, dissolved in 28 ecm of water, are mixed with 30 ecm of a solution of aminoacetic acid in water (1:10) and mixed with 1 g of an action product of about 10 moles of ethylene oxide to 1 mole of nonylphenol, 3 g of soda and water 11 filled up. In this solution, the dyed material in a liquor ratio is 1: 20 post-treated by heating from 60 to 95 ° C and treated for 30 minutes at 95 0 C. Then for 15 minutes at 95 0 C with 1 g of an action product of about 10 moles of ethylene oxide on 1 mole of nonylphenol and 3 g of soda in liter of water, soaped, rinsed and dried.
4040
worin R1, R2 und R3 die oben angegebene Bedeutung haben, vereinigt.in which R 1 , R 2 and R 3 have the meaning given above, combined.
Gegenüber dem aus der französischen Patentschrift 981 432, Tabellenbeispiel 11 auf Seite 9, bekannten kupferhaltigen Disazofarbstoff zeichnen sich die verfahrensgemäß erhältlichen Farbstoffe vergleichbarer Konstitution durch eine bessere Wasch- und Lösungsmittelechtheit der Baumwollfärbungen aus.Compared to that from the French patent specification 981 432, table example 11 on page 9, known copper-containing disazo dye, the dyes obtainable according to the process are more comparable Constitution through better washing and solvent fastness of the cotton dyeings.
Baumwollgarn wird im Flottenverhältnis 1:20 45 Minuten bei 35 0C in dem nachstehend beschriebenen Grundierungsbad behandelt, abgeschleudert und zunächst 10 Minuten bei 2O0C und dann nach langsamer Erwärmung auf 90 bis 95° C bis 30 Minuten bei 90 bis 95° C in dem nachstehend beschriebenen Entwicklungsbad entwickelt. Dann wird gespült und zunächst 15 Minuten bei 6O0C, dann 15 Minuten bei 95 0C mit 1 g eines Einwirkungsproduktes von etwa 10 Mol Äthylenoxyd auf 1 Mol Nonylphenol und 3 g Soda im Liter Wasser geseift, gespült und getrocknet. Cotton yarn is treated at a liquor ratio of 1:20 for 45 minutes at 35 0 C in the below-described Grundierungsbad, spun down and initially 10 minutes at 2O 0 C and then slowly heating to 90 to 95 ° C to 30 minutes at 90 to 95 ° C in developed in the development bath described below. Then, it is rinsed and initially 15 minutes at 6O 0 C, then 15 minutes at 95 0 C with 1 g of the action product of about 10 moles of ethylene oxide to 1 mol of nonylphenol and 3 g of soda per liter water, soaped, rinsed and dried.
GrundierungsbadPrimer bath
4,5 g l-(2',3'-Oxynaphthoylamino)-2,4-dimethoxy-5-chlorbenzol werden in 13,5 ecm denaturiertem Äthylalkohol, 1,5 ecm Natronlauge von 380Be, 4,5 ecm warmem Wasser und 1,5 ecm Formaldehydlösung, Grundierungsbad4.5 g of l- (2 ', 3'-oxynaphthoylamino) -2,4-dimethoxy-5-chlorobenzene in 13.5 cc of denatured ethyl alcohol, 1.5 cc of sodium hydroxide solution 38 0 Be, 4.5 cc of warm water and 1.5 ecm formaldehyde solution, primer bath
1,75 g 2-(',3'-Oxynaphthoylamino)-naphthalin werden in 3,5 ecm denaturiertem Äthylalkohol, 0,9 ecm Natronlauge von 380Be, 1,8 ecm warmem Wasser und 0,9 ecm Formaldehydlösung, 33°/oig> gelöst. Die so erhaltene Lösung wird mit Wasser von 350C, das 3 g eines Kondensationsproduktes aus höhermolekularen Fettsäuren und Eiweißabbauprodukten und 10 ecm Natronlauge von 38° Be enthält, auf 11- eingestellt. 1.75 g of 2 - (', 3'-oxynaphthoylamino) naphthalene are dissolved in 3.5 ecm denatured ethyl alcohol, 0.9 ecm sodium hydroxide solution of 38 0 Be, 1.8 ecm warm water and 0.9 ecm formaldehyde solution, 33 ° / o ig> solved. The solution thus obtained is diluted with water of 35 0 C, which contains 3 g of a condensation product of higher molecular weight fatty acids and protein degradation products, and 10 cc of sodium hydroxide solution of 38 ° Be is adjusted to 11-.
EntwicklungsbadDeveloping bath
3,3 g 7-Amino-5-methyl-4-(2'-methoxy-5'-nitrophenyl-l'-azo)-benzimidazol werden mit 6 ecm Salzsäure von 20° Be, 18 ecm Essigsäure und 4 ecm Natriumnitritlösung 1: 5 diazotiert und die so erhaltene Diazolösung in ein Bad gegeben, das in 11 Wasser 2 g eines Einwirkungsproduktes von etwa 20 Mol Äthylenoxyd auf 1 Mol Octadecylalkohol und 20 g Natriumacetat enthält.3.3 g of 7-amino-5-methyl-4- (2'-methoxy-5'-nitrophenyl-1'-azo) benzimidazole are with 6 ecm hydrochloric acid of 20 ° Be, 18 ecm acetic acid and 4 ecm sodium nitrite solution 1: 5 diazotized and the diazo solution thus obtained is placed in a bath that is dissolved in 11 water 2 g of an action product of about 20 moles of ethylene oxide to 1 mole of octadecyl alcohol and 20 g Contains sodium acetate.
Man erhält eine Schwarzfärbung von guten Licht- und Naßechtheiten.A black dyeing with good light and wet fastness properties is obtained.
42 Gewichtsteile 7-Amino-5-methyl-4-(2'-methoxyphenyl-l'-azo)-benzimidazol werden mit 120 Volumteilen Essigsäure angeteigt. Nach Zugabe von 45 Volumteilen konzentrierter Salzsäure wird auf 00C abgekühlt und durch Zugabe von 10,5 Gewichtsteilen Natriumnitrit in Form einer konzentrierten, wäßrigen42 parts by weight of 7-amino-5-methyl-4- (2'-methoxyphenyl-l'-azo) benzimidazole are made into a paste with 120 parts by volume of acetic acid. After addition of 45 parts by volume of concentrated hydrochloric acid is cooled to 0 0 C and concentrated by the addition of 10.5 parts by weight of sodium nitrite in the form of aqueous
Lösung und nachfolgendes rasches Erwärmen auf 35 bis 400C diazotiert. Dann wird mit Wasser auf etwa 1000 Volumteile verdünnt. Die so erhaltene Diazolösung läßt man unter gutem Rühren in eine wie folgt bereitete Lösung von 2,3-Oxynaphthoylaminobenzol eintropfen: 39,5 Gewichtsteile 2,3-Oxynaphthoylaminobenzol werden in 60 Volumteilen Alkohol und 75 Volumteiien 5 η-Natronlauge gelöst und mit 3000 Volumteilen Wasser, in denen 200 Gewichtsteile Natriumcarbonat gelöst sind, versetzt. Nach Beendigung der Kupplung wird eine Lösung von 19 Gewichtsteilen Kupfersulfat und 90 Volumteilen Triäthanolamin in 300 Volumteilen Wasser zugegeben. Anschließend wird auf 95 0C erwärmt und 2 Stunden bei dieser Temperatur behandelt. Die gebildete Kupferkomplexverbindung des Farbstoffes wird abfiltriert, gewaschen und getrocknet. Sie stellt ein dunkles Pulver dar. Die nachstehende Tabelle enthält noch eine Anzahl von weiteren erfindungsgemäß verwendbaren v Komponenten sowie die Farbtöne der daraus auf der FaserSolution and subsequent rapid heating to 35 to 40 0 C diazotized. Then it is diluted to about 1000 parts by volume with water. The diazo solution thus obtained is added dropwise, with thorough stirring, to a solution of 2,3-oxynaphthoylaminobenzene prepared as follows: 39.5 parts by weight of 2,3-oxynaphthoylaminobenzene are dissolved in 60 parts by volume of alcohol and 75 parts by volume of 5 η sodium hydroxide solution and 3000 parts by volume of water , in which 200 parts by weight of sodium carbonate are dissolved, added. After the coupling has ended, a solution of 19 parts by weight of copper sulfate and 90 parts by volume of triethanolamine in 300 parts by volume of water is added. It is then heated to 95 ° C. and treated at this temperature for 2 hours. The copper complex compound formed in the dye is filtered off, washed and dried. It is a dark powder. The following table contains a number of further useful in the invention v components, and the hues of the fact on the fiber
ίο erhältlichen metallhaltigen Azofarbstoffe, die eben* falls gute Echtheitseigenschaften besitzen.ίο available metal-containing azo dyes, which just * if they have good fastness properties.
Kobaltkomplexhue
Cobalt complex
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
3-nitrobenzoll- (2 ', 3' -oxynaphthoylamino) -
3-nitrobenzene
oxyphenyl-l'-azo)-benz-
imidazöl7-amino-5-methyl-4- (2'-meth-
oxyphenyl-l'-azo) -benz-
imidaz oil
. amino)-3,3'-dimethoxydi-
phenyl4,4'-bis (2 ", 3" -oxynaphthoyl-
. amino) -3,3'-dimethoxydi-
phenyl
schwarzBrown
black
braunblack
Brown
braunblack
Brown
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
oylaminö)-2,5-dimethoxy-
benzoll- (3 '-oxydiphenylenoxy-2'-carb-
oylaminö) -2,5-dimethoxy-
benzene
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-l'-azo) -benz-
imidazole
amino)-4-chlorbenzoll- (2'-oxycarbazole-3'-carboyl-
amino) -4-chlorobenzene
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-l'-azo) -benz-
imidazole
amino)-2-methylbenzoll- (2'-oxyanthracene-3'-carboyl-
amino) -2-methylbenzene
Graugreenish
Gray
oxyphenyl-1 '~azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '~ azo) -benz-
imidazole
azol-4'-carboylamino)-4-meth-
oxybenzoll- (5'-Oxy-l ', 2'-l ", 2" -benzocarb-
azole-4'-carboylamino) -4-meth-
oxybenzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
azol-4'-carboylamino)-2-me-
thyl-4-methoxybenzoll- (5'-Oxy-l ', 2'-l ", 2" -benzocarb-
azole-4'-carboylamino) -2-me-
ethyl 4-methoxybenzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
3,3 '-dimethyldiphenyl4,4'-bis-acetoacetylamineq-
3,3'-dimethyldiphenyl
Violettblunt
violet
braunDark
Brown
braunDark
Brown
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
amino-2,4-dimethoxy-5-chlor-
benzol)Terephthaloyl-bis- (l -acetyl-
amino-2,4-dimethoxy-5-chloro
benzene)
schwarzblue
black
Schwarzbrownish
black
braunblack
Brown
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
oylamino)-naphthalinl- (3'-oxydiphenylenoxy-2'-carb-
oylamino) naphthalene
Graubrownish
Gray
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-l'-azo) -benz-
imidazole
oylamino)-2-äthoxybenzoll- (3'-oxydiphenylenoxy-2'-carb-
oylamino) -2-ethoxybenzene
Graubrownish
Gray
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
amino-2-methoxy-4-chlor-
5-methylbenzol)Terephthaloyl-bis- (l-acetyl-
amino-2-methoxy-4-chloro
5-methylbenzene)
Schwarzreddish
black
braunblack
Brown
braunblack
Brown
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
benzthiazol2-acetoacetylamino-6-ethoxy-
benzthiazole
Blaugreenish
blue
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-l'-azo) -benz-
imidazole
oxy-4-chlorbenzoll-acetoacetylamino-2,5-dimeth-
oxy-4-chlorobenzene
Blaureddish
blue
Blaureddish
blue
Kobaltkomplexhue
Cobalt complex
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
methylbenzoll-acetoacetylamino-2,5-di-
methylbenzene
Blaureddish
blue
Blaureddish
blue
thyl-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-5'-chlorophenyl-l'-azo) -
benzimidazole
thyl-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-5'-chlorophenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
thyl-5'-chlorphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-5'-chlorophenyl-l'-azo) -
benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
oxy-5 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5 '-nitrophenyl-1' -azo) -
benzimidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
oxy-5'-nitroptienyl-l'-azo)-
benzimidazol7-amine ~ 5-methyl-4- (2'-meth-
oxy-5'-nitroptienyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2-methoxy-4-chlor-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloro-5-methyl-
benzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
oxy- 5 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy- 5 '-nitrophenyl-1' -azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
oxy-5'-nitrophenyl-l'-äzo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-Ammo-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
oxy-5'-nitrophenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
oxy-5'-nitrophenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2-methylbenzoll- (2 ', 3' -oxynaphthoylamino) -
2-methylbenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
ίοίο
Kobaltkomplexhue
Cobalt complex
4-(2'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
l'-azo) benzimidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3 '-me-
ethylphenyl-1 '-azo) -benz-
imidazole
2-methoxy-4-chlor-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloro-5-methyl-
benzene
thylphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-l'-azo) -benz-
imidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3 '-me-
ethylphenyl-1 '-azo) -benz-
imidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
thylphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-l'-azo) -benz-
imidazole
2,4-dimethoxy-5-chlorbenzoli- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
thylphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-l'-azo) -benz-
imidazole
2-äthoxybenzolI- (2 ', 3'-oxynaphthoylamino) -
2-ethoxybenzene
thylphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-l'-azo) -benz-
imidazole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
thylphenyl-l'-azo)-benz-
imidazol7-amine-5-methyl-4- (3'-me-
ethylphenyl-l'-azo) -benz-
imidazole
amino)-2-methoxybenzoll- (6'-bromo-2 ', 3'-oxynaphthoyl-
amino) -2-methoxybenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3 '-me-
ethylphenyl-1 '-azo) -benz-
imidazole
4-methylbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methylbenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
4-äthoxybenzolJ .- (2 ', 3'-Oxynaphthoylamino) -
4-ethoxybenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
2,4-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethylbenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (3'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
2,3-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,3-dimethylbenzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxy-5'-chlor-
phenyl-l'-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-l'-azo) -benzimide-
azole
2-methoxy-benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-benzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
Kobaltkomplex Ihue
Cobalt complex I.
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-Ammo-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
phenyl-l'-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-nitro-
phenyl-l'-azo) -benzimide-
azole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2-methylbenzolI- (2 ', 3'-oxynaphthoylamino) -
2-methylbenzene
nyl-5'-imino-4',5'-dihydro-
1,2,4-triazolyl-3 '-azo)-
benzimidazol7-amino-5-methyl-4- (l '-phe-
nyl-5'-imino-4 ', 5'-dihydro-
1,2,4-triazolyl-3'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3 '-chlor-
phenyl-1 '-azo) -benzimide-
azole
3-methoxydiphenyleaoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenyleaoxide
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(2',5'-dichlorphenyl-
1'-azo)-benzimidazol7-amino-5-methyl-
4- (2 ', 5'-dichlorophenyl-
1'-azo) benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
thyl-4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-4'-chlorophenyl-l'-azo) -
benzimidazole
3-methoxydiphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenylene oxide
thyl-4-f2'-methyl-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-4-f2'-methyl-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-ethoxybenzene
thyl-1 '-azo)-benzimidazol7-amino-5-methyl-4- (naph-
ethyl-1'-azo) -benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
lyl-8'-azo)-benzimidazol7-amino-5-methyl-4- (quino-
lyl-8'-azo) benzimidazole
thyl-o'-chlor-benzimid-
azolyl-7'-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-o'-chloro-benzimide-
azolyl-7'-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
oxy-4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-4'-chlorophenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
Kobaltkomplexhue
Cobalt complex
nylazo-benzimidazol7-amino-2,5-dimethyl-4-phe-
nylazo-benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(3'-nitrophenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-nitrophenyl-l'-azo) -
benzimidazole
3-methoxydiphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenylene oxide
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-4- (2'-chloro-5'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4'-methylphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-nitro-
4'-methylphenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3> oxynaphthoylamino) -
naphthalene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-eth-
oxyphenyl-1 '-azo) -benz-
imidazole
naphthalin2- (2 ', 3' -oxynaphthoylamino) -
naphthalene
4-(3 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3 '-nitrophenyl-1' -azo) -
benzimidazole
3-methoxydiphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenylene oxide
4-(2'-methoxy-4'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methoxy-5-chlorbenzol1- (2 ', 3'-oxynaphthoylamino>
2-methoxy-5-chlorobenzene
4-(4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4-(2',5'-dimethoxy-4'-ben-
zoyl-aminophenyl-l'-azo)
bqnzimidazol7-amino-5-methyl-
4- (2 ', 5'-dimethoxy-4'-ben-
zoyl-aminophenyl-l'-azo)
bqnzimidazole
3-methoxydiphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenylene oxide
4-(3'-chlorphenyl-1'-azo)-
benzimidazol ·7-amino-2,5-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(4'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (4'-methoxyphenyl-
1'-azo) -benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(4'-acetylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-acetylphenyl-l'-azo) -
benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(naphthyl-2'-azo)-benz-
imidazol7-amino-2,5-dimethyl-
4- (naphthyl-2'-azo) -benz-
imidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-[2'-(4"-chlorphenoxy)-
5'-chlorphenyl-l'-azo]-
benzimidazol7-amino-2,5-dimethyl-
4- [2 '- (4 "-chlorophenoxy) -
5'-chlorophenyl-l'-azo] -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(2'-methylsulfonyl-
4'-nitrophenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-methylsulfonyl-
4'-nitrophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
Kobaltkomplexhue
Cobalt complex
nylazo-benzimidazol7-amino-2,6-dimethyl-4-phe-
nylazo-benzimidazole
Dunkelblaureddish
Dark blue
Schwarz
blaugreenish
black
blue
nylazo-benzimidazol7-amino-2,6-dimethyl-4-phe-
nylazo-benzimidazole
naphthalin2- (2 ', 3' -oxynaphthoylamino) -
naphthalene
Dunkelblaureddish
Dark blue
Schwarz
blaugreenish
black
blue
nylazo-benzimidazol7-amino-2,6-dimethyl-4-phe-
nylazo-benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
Dunkelblaureddish
Dark blue
Schwarz
blaugreenish
black
blue
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
Dunkelblaureddish
Dark blue
stichiges
Schwarz
blaugreen
prickly
black
blue
4-(2'-chlorphenyl-l '-azo>
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo>
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
Dunkelblaureddish
Dark blue
stichiges
Schwarzblaugreen
prickly
Black blue
4-(2'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
blau-Black-
blue-
stichiges
Schwarzblaugreen
prickly
Black blue
4-(3 '-chlorphenyl-1 '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
blauBlack-
blue
stichiges
Schwarz
blaugreen
prickly
black
blue
4-(3 '-chlorphenyl-1 '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
blaublack
blue
stichiges
Schwarz
blaugreen
prickly
black
blue
4-(3 '-chlorphenyl-1 '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
blaublack
blue
stichiges
Schwarz
blaugreen
prickly
black
blue
komplexCopper-
complex
komplexcobalt
complex
Nickel
komplexhue
nickel
complex
komplexiron
complex
komplexzinc
complex
4-(2'-methoxy-phenyl-
1 '-azo)-benzimidazol
7-Amino-5-methyl-
4-(2'-methoxy-phenyl-
l'-azo)-benzimidazol7-amino-5-methyl-
4- (2'-methoxy-phenyl-
1'-azo) -benzimidazole
7-amino-5-methyl-
4- (2'-methoxy-phenyl-
l'-azo) benzimidazole
amino)-naphthalin
l-(2)'3'-Oxynaphthoyl-
amino)-2,4-dimeth-
oxy-5-chlorbenzol2- (2 ', 3'-oxynaphthoyl-
amino) naphthalene
l- (2) '3'-oxynaphthoyl-
amino) -2,4-dimeth-
oxy-5-chlorobenzene
Schwarzblack
black
Schwarzblack
black
Schwarzblack
black
Schwarzblack
black
Schwarzblack
black
Kobaltkomplexhue
Cobalt complex
nyl-5'-imino-4',5'-dihydro-
1,2,4-triazolyl-3 '-azo>
benzimidazol7-amino-5-methyl-4- (l'-phe-
nyl-5'-imino-4 ', 5'-dihydro-
1,2,4-triazolyl-3'-azo>
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylammo) -
3-nitrobenzene
nyl-5'-imino-4',5'-dihydro-
1,2,4-triazolyl-3 '-azo)-
benzimidazol7-amino-5-methyl-4- (l '-phe-
nyl-5'-imino-4 ', 5'-dihydro-
1,2,4-triazolyl-3'-azo) -
benzimidazole
4-chlorbenzoll- (2 ', 3' -oxynaphthoylamino) -
4-chlorobenzene
nyl-5'-imino-4',5'-dihydro-
1,2,4-triazolyl-3 '-azo)-
benzimidazol7-amino-5-methyl-4- (l'-phe-
nyl-5'-imino-4 ', 5'-dihydro-
1,2,4-triazolyl-3'-azo) -
benzimidazole
. 2-methyl-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
. 2-methyl-5-chlorobenzene
nyl-5'-imino-4',5'-dihydro-
l,2,4-triazolyl-3'-azo)-
benzimidazol7-amino-5-methyl-4- (l '-phe-
nyl-5'-imino-4 ', 5'-dihydro-
l, 2,4-triazolyl-3'-azo) -
benzimidazole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
Kobaltkomplexhue
Cobalt complex
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
" 4-methoxybenzol1 - (2 ', 3' -oxynaphthoylamino) -
"4-methoxybenzene
azo-benzimidazol7-amino-5-methyl-4-phenyl-
azo-benzimidazole
4-chlorbenzol. l- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-nitro-
phenyl-1 '-azo) -benzimide-
azole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
phenyl-l'-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-nitro-
phenyl-l'-azo) -benzimide-
azole
2-methyl-4-methoxybenzol 1- (T, 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
benzol2,3-oxynaphthoylamino
benzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-meth-
oxyphenyl-1 '-azo) -benz-
imidazole
2-metb.oxy-4-chlor-5-metb.yl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-metb.oxy-4-chloro-5-metb.yl-
benzene
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-meth-
oxyphenyl-l'-azo) -benz-
imidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3 '-chlor-
phenyl-1 '-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-methoxybenzol1, (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3 '-chlor-
phenyl-1 '-azo) -benzimide-
azole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (3'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
phenyl-l'-azo)-benzimid-
azol7-amino-5-methyl-4- (4'-chloro-
phenyl-l'-azo) -benzimide-
azole
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
Kobaltkomplexhue
Cobalt complex
4-(2',5'-dichlorphenyl-
l'-azo)-benzimidazol7-amino-5-methyl-
4- (2 ', 5'-dichlorophenyl-
l'-azo) benzimidazole
naphthalinl- (2 '^' - Oxynaphthoylamino) -
naphthalene
4-(2',5'-dichlorphenyl-
1 '-azo)-benzimidazol7-amino-5-methyl-
4- (2 ', 5'-dichlorophenyl-
1'-azo) -benzimidazole
2-methylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methylbenzene
4-(2',5'-dichlorphenyl-
1 '-azo)-benzimidazol7-amino-5-methyl-
4- (2 ', 5'-dichlorophenyl-
1'-azo) -benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4-(2',5'-dichlorphenyl-
1 '-azo)-benzimidazol7-amino-5-methyl-
4- (2 ', 5'-dichlorophenyl-
1'-azo) -benzimidazole
2-methyl-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-5-chlorobenzene
thyl-4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-4'-chlorophenyl-l'-azo) -
benzimidazole
thyl-4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-4'-chlorophenyl-l'-azo) -
benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
thyl-4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-4'-chlorophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
thyl-4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-4'-chlorophenyl-l'-azo) -
benzimidazole
2,4-dimethoxybenzoll- (2 ', 3' -oxynaphthoylamino) -
2,4-dimethoxybenzene
thyl-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-5'-nitrophenyl-l'-azo) -
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
thyl-5'-nitrophenyl-l'-azö)-
benzimidazol7-amino-5-methyl-4- (2'-me-
thyl-5'-nitrophenyl-l'-azo) -
benzimidazole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
thyl-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-5'-nitrophenyl-l'-azo) -
benzimidazole
2,3-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,3-dimethylbenzene
thyl-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-me-
ethyl-5'-nitrophenyl-l'-azo) -
benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,5-diöiethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-diiethoxybenzene
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
8'-azo-benzimidazol7-amino-5-methyl-4-quinolyl-
8'-azo-benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
8'-azo)-benzimidazol7-amino-5-methyl-4-quinolyl-
8'-azo) benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
8'-azo-benzimidazol7-Alnino-5-methyl-4-quinolyl-
8'-azo-benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
Iblack
I.
8'-azo)-benzimidazol7-amino-5-methyl-4-quinolyl-
8'-azo) benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
Kobaltkomplexhue
Cobalt complex
thyl-ö'-chlor-benzimid-
azolyl-7'-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-ö'-chloro-benzimide-
azolyl-7'-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
thyl-6'-chlor-benzimid-
azolyl-7'-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-6'-chloro-benzimide-
azolyl-7'-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
thyl-o'-chlor-benzimid-
azolyl-7'-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-o'-chloro-benzimide-
azolyl-7'-azo) -benzimide-
azole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
thyl-6'-chlor-benzimid-
azolyl-7 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2'-me-
ethyl-6'-chloro-benzimide-
azolyl-7'-azo) -benzimide-
azole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-methb
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
oxy-5'-chlorphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-phenylazo-benzimidazol7-amino-2,5-dimethyl-
4-phenylazo-benzimidazole
4-phenylazo-benzimidazol7-amino-2,5-dimethyl-
4-phenylazo-benzimidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-phenylazo-benzimidazol7-amino-2,5-dimethyl-
4-phenylazo-benzimidazole
2-methoxy-4-chlor-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloro-5-methyl-
benzene
4-phenylazo-benzimidazol7-amino-2,5-dimethyl-
4-phenylazo-benzimidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
4-(2'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
l'-azo) benzimidazole
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (2'-methoxyphenyl-
l'-azo) benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4-(2'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
3-methoxydiphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxydiphenylene oxide
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
2-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-ethoxybenzene
Kobaltkomplexhue
Cobalt complex
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(3 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3 '-nitrophenyl-1' -azo) -
benzimidazole
naphthalinl- (2 ', 3' -oxynaphthoylamino) -
naphthalene
4-(3'-nitrophenyl-1'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-nitrophenyl-1'-azo) -
benzimidazole
2-methyl-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-5-chlorobenzene
4-(3'-nitrophenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-nitrophenyl-l'-azo) -
benzimidazole
2-methylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methylbenzene
4-(3 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3 '-nitrophenyl-1' -azo) -
benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
2,5-dimethoxybenzol1-C2 ', 3' -oxynaphthoylamino) -
2,5-dimethoxybenzene
thylphenyl-1 '-azo)-benz-
iraidazol7-amino-5-methyl-4- (2'-me-
ethylphenyl-1 '-azo) -benz-
iraidazol
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
thylphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-me-
ethylphenyl-l'-azo) -benz-
imidazole
2-methoxyT5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxyT5-chlorobenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (2'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
4-methylbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methylbenzene
thylphenyl-l'-azo)-benz-
imidazol7-amino-4- (2'-chloro-5'-me-
ethylphenyl-l'-azo) -benz-
imidazole
2,4-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethylbenzene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-4- (2'-chloro-5'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
thylphenyl-l'-azo)-benz-
imidazol7-amino-4- (2'-chloro-5'-me-
ethylphenyl-l'-azo) -benz-
imidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
thylphenyl-1 '-azo)-benz-
imidazol7-amino-4- (2'-chloro-5'-me-
ethylphenyl-1 '-azo) -benz-
imidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4'-methylphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-nitro-
4'-methylphenyl-l'-azo) -
benzimidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4'-methylphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-nitro-
4'-methylphenyl-l'-azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4'-methylphenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2 < -nitro-
4'-methylphenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4'-methylphenyl-l '-azo)-
benzimidazol7-amino-5-methyl-4- (2'-nitro-
4'-methylphenyl-l'-azo) -
benzimidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
oxyphenyl-1 '-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-eth-
oxyphenyl-1 '-azo) -benz-
imidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-eth-
oxyphenyl-l'-azo) -benz-
imidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
Kobaltkomplexhue
Cobalt complex
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-eth-
oxyphenyl-l'-azo) -benz-
imidazole
2-äthoxybenzol.l- (2 ', 3'-oxynaphthoylamino) -
2-ethoxybenzene.
oxyphenyl-l'-azo)-benz-
imidazol7-amino-5-methyl-4- (4'-eth-
oxyphenyl-l'-azo) -benz-
imidazole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
4-(3 '-nitrophenyl-1 '-azo)-
benzimidazol7-amine-2,5-dimethyl-
4- (3 '-nitrophenyl-1' -azo) -
benzimidazole
4-(3'-nitrophenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-nitrophenyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(3'-nitrophenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-nitrophenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(3 '-nitrophenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3 '-nitrophenyl-1' -azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxy-4'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxy-4'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(2'-methoxy-4'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4-(2'-methoxy-4'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,5-dimethyl-
4- (2'-methoxy-4'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
2-methoxy-4-chloΓ-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloΓ-5-methyl-
benzene
4-(4'-chloφhenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-chloφhenyl-l'-azo) -
benzimidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
4-(4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
2-methylbenzoll- (2 ', 3'-oxynaphthb.oylamino) -
2-methylbenzene
4-(4'-chlorphenyl-i '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-chlorophenyl-i'-azo) -
benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
methoxy-4'-benzoylamino-
phenyl-l'-azo)-benzimid-
azol7-amino-5-methyl-4- (2 ', 5'-di-
methoxy-4'-benzoylamino
phenyl-l'-azo) -benzimide-
azole
methoxy-4'-benzoylamino-
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2 ', 5'-di-
methoxy-4'-benzoylamino
phenyl-1 '-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
methoxy-4'-benzoylämino-
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2 ', 5'-di-
methoxy-4'-benzoylamino-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
Kobaltkomplexhue
Cobalt complex
meth xy-4'-benzoylamino-
phenyl-1 '-azo)-benzimid-
azol7-amino-5-methyl-4- (2 ', 5'-di-
meth xy-4'-benzoylamino-
phenyl-1 '-azo) -benzimide-
azole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(3'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-chlorophenyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(3'-chlorphenyl-1'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
4-(3'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-5-chlorobenzene
4-(3'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-chlorophenyl-l'-azo) -
benzimidazole
2,3-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,3-dimethylbenzene
4-(4'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (4'-methoxyphenyl-
l'-azo) benzimidazole
2-methylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methylbenzene
4-(4'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (4'-methoxyphenyl-
1'-azo) -benzimidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
4-(4'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (4'-methoxyphenyl-
1'-azo) -benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(4'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-2,5-dimethyl-
4- (4'-methoxyphenyl-
l'-azo) benzimidazole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
4-(4'-acetylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-acetylphenyl-l'-azo) -
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(4'-acetylphenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-acetylphenyl-l'-azo) -
benzimidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(4'-acetylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-acetylphenyl-l'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(4'-acetylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (4'-acetylphenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(naphthyl-2'-azo)-benz-
imidazol7-amino-2,5-dimethyl-
4- (naphthyl-2'-azo) -benz-
imidazole
^-methyl-S-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
^ -methyl-S-chlorobenzene
4-(naphthyl-2'-azo)-benz-
imidazol7-amino-2,5-dimethyl-
4- (naphthyl-2'-azo) -benz-
imidazole
2,3-dimethylbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,3-dimethylbenzene
4-(naphthyl-2'-azo)-benz-
imidazol7-amino-2,5-dimethyl-
4- (naphthyl-2'-azo) -benz-
imidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
4-(naphthyl-2'-azo)-benz-
imidazol7-amino-2,5-dimethyl-
4- (naphthyl-2'-azo) -benz-
imidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
j
i black
j
i
4- [2'-(4' '-chlorphenoxy)-
5'-chlorphenyl-l'-azo]-
benzimidazol7-amino-2,5-dimethyl-
4- [2 '- (4''-chlorophenoxy) -
5'-chlorophenyl-l'-azo] -
benzimidazole
Kobaltkomplexhue
Cobalt complex
4- [2'-(4' '-chlorphenoxy)-
5'-chlorphenyl-l'-azo]-
benzimidazol7-amine-2,5-dimethyl-
4- [2 '- (4''-chlorophenoxy) -
5'-chlorophenyl-l'-azo] -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4- [2'-(4"-chlorphenoxy)-
5'-chlorphenyl-l'-azo]-
benzimidazol7-amino-2,5-dimethyl-
4- [2 '- (4 "-chlorophenoxy) -
5'-chlorophenyl-l'-azo] -
benzimidazole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
4-[2'-(4"-chlorphenoxy)-
5'-chlorphenyl-l '-azo]-
benzimidazol7-amino-2,5-dimethyl-
4- [2 '- (4 "-chlorophenoxy) -
5'-chlorophenyl-l'-azo] -
benzimidazole
2-äthoxybenzoll- (2 ', 3'-oxynaphthoylasiino) -
2-ethoxybenzene
4-(2'-methylsulfonyl-
4'-nitrophenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-methylsulfonyl-
4'-nitrophenyl-l'-azo) -
benzimidazole
2-methoxy-4-chlor-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloro-5-methyl-
benzene
4-(2'-methylsulfonyl-
4'-Hitrophenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-methylsulfonyl-
4'-Hitrophenyl-l'-azo) -
benzimidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
4-(2'-methylsulfonyl-
4'-nitrophenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-methylsulfonyl-
4'-nitrophenyl-l'-azo) -
benzimidazole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
4-(2'-methylsulfonyl-
4'-nitrophenyl-l '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (2'-methylsulfonyl-
4'-nitrophenyl-l'-azo) -
benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
4-(2'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(2'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
2-methyl-4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-methoxybenzene
4-(2'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (2'-chlorophenyl-l'-azo) -
benzimidazole
3-methoxydiphenylenoxyd2- (2 ', 3' -oxynaphthoylamino) -
3-methoxydiphenylene oxide
nylazo-benzimidazol7-amino-5-methoxy-4-phe-
nylazo-benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
nylazo-benzimidazol7-amino-5-methoxy-4-phe-
nylazo-benzimidazole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
nylazo-benzimidazol7-amino-5-methoxy-4-phe-
nylazo-benzimidazole
2, S-dimethoxy^-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2, S-dimethoxy ^ -chlorobenzene
nylazo-benzimidazol7-amino-5-methoxy-4-phe-
nylazo-benzimidazole
2-methyl-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-5-chlorobenzene
nylazo-benzimidazol7-amino-5-methoxy-4-phe-
nylazo-benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(3 '-methylphenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-methylphenyl-1'-azo) -
benzimidazole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(3 '-methylphenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-methylphenyl-1'-azo) -
benzimidazole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(3'-methylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-methylphenyl-l'-azo) -
benzimidazole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
Kobaltkomplexhue
Cobalt complex
4-(3'-methylphenyl-l'-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-methylphenyl-l'-azo) -
benzimidazole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(3 '-methylphenyl-1 '-azo)-
benzimidazol7-amino-2,5-dimethyl-
4- (3'-methylphenyl-1'-azo) -
benzimidazole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
4-(2'-methoxy-5'-nitro-
phenyl-l'-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-nitro-
phenyl-l'-azo) -benzimide-
azole
3-nitrobenzoll- (2 ', 3' -oxynaphthoylamino) -
3-nitrobenzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2-methylbenzoll- (2 ', 3' -oxynaphthoylamino) -
2-methylbenzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2,5-dimethoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxybenzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
4-(2'-methoxy-5'-chlor-
phenyl-l'-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-l'-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
liches
Korinthblack-
liches
Corinth
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-2,6-dimethyl-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
liches
Korinthblack
liches
Corinth
oxy-5'-nitrophenylTl'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenylTl'-azo) -
benzimidazole
carbazol-4'-carboylamino)-
4-methoxybenzoll- (5'-oxy-l ', 2', l ", 2" -benzo-
carbazole-4'-carboylamino) -
4-methoxybenzene
liches
Korinthblack
liches
Corinth
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
carbazol-4'-carboylamino)-
2-methyl-4-methoxybenzoll- (5'-oxy-l ', 2', l ", 2" -benzo-
carbazole-4'-carboylamino) -
2-methyl-4-methoxybenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
amino)-3,3'-dimethoxy-
diphenyl4,4'-bis (2 ", 3" -oxynaphthoyl-
amino) -3,3'-dimethoxy-
diphenyl
Schwarzbrownish
black
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
amino)-4-chlorbenzoll- (2'-oxycarbazole-3 '-carboyl-
amino) -4-chlorobenzene
Schwarzbrownish
black
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2'-carboylamino)-2,5-dimeth
oxybenzoll- (3'-oxydiphenylene oxide
2'-carboylamino) -2,5-dimeth
oxybenzene
Graubrownish
Gray
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2'-carboylamino)-naphthalinl- (3'-oxydiphenylene oxide
2'-carboylamino) naphthalene
Graubrownish
Gray
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
2'-carboylamino)-2-äthoxy-
benzoll- (3'-oxydiphenylene oxide
2'-carboylamino) -2-ethoxy-
benzene
Kobaltkomplexhue
Cobalt complex
Graubrownish
Gray
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-methyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
amino)-2-methylbenzoll- (2'-oxyanthracene-3'-carboyl-
amino) -2-methylbenzene
Grau
schwarzgreenish
Gray
black
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2-methyl-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methyl-4-chlorobenzene
4-(2'-methoxy-5'-chlor-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-chloro-
phenyl-1 '-azo) -benzimide-
azole
2,4-dimethoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,4-dimethoxy-5-chlorobenzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
3-nitrobenzoll- (2 ', 3'-oxynaphthoylamino) -
3-nitrobenzene
4-(2'-methoxy-5 '-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5 '-nitro-
phenyl-1 '-azo) -benzimide-
azole
naphthalinl- (2 ', 3'-oxynaphthoylamino) -
naphthalene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
4-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-methoxybenzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
2-methoxy-4-chloΓ-5-methyl-
benzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloΓ-5-methyl-
benzene
4-(2'-methoxy-5'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-dimethoxy-
4- (2'-methoxy-5'-nitro-
phenyl-1 '-azo) -benzimide-
azole
3-methoxy-diphenylenoxyd2- (2 ', 3'-oxynaphthoylamino) -
3-methoxy-diphenylene oxide
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-5,6-dimethoxy-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
2-methoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxybenzene
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-5,6-dimethoxy-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
2-methylbenzoll- (2 ', 3' -oxynaphthoylamino) -
2-methylbenzene
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-5,6-dimethoxy-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(2'-methoxyphenyl-
l'-azo)-benzimidazol7-amino-5,6-dimethoxy-
4- (2'-methoxyphenyl-
l'-azo) benzimidazole
2,5-dimethoxybenzoll- (2 ', 3'-Qxynaphthoylamino) -
2,5-dimethoxybenzene
4-(2'-methoxyphenyl-
1 '-azo)-benzimidazol7-amino-5,6-dimethoxy-
4- (2'-methoxyphenyl-
1'-azo) -benzimidazole
4-äthoxybenzol1 »(2 ', 3'-Oxynaphthoylamino) -
4-ethoxybenzene
Kobaltkomplexhue
Cobalt complex
4-(4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
4-(4'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino>
naphthalene
4-(4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
4-chlorbenzol1- (2 ', 3'-oxynaphthoylamino>
4-chlorobenzene
4-(4'-chlorphenyl-l '-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (4'-chlorophenyl-l'-azo) -
benzimidazole
2-methoxy-5-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-5-chlorobenzene
4-(4'-chlorphenyl-i'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (4'-chlorophenyl-i'-azo) -
benzimidazole
4-äthoxybenzoll- (2 ', 3'-oxynaphthoylamino) -
4-ethoxybenzene
lyl-8 '-azo)-benzimidazol7-amino-5-methyl-4- (chiho-
lyl-8'-azo) -benzimidazole
lyl-8'-azo)-benzimidazol7-amino-5-methyl-4- (quino-
lyl-8'-azo) benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
thyl-benzimidazolyl-7'-azo)-
benzimidazol7-amino-5-methyl-4- (5'-me-
ethyl-benzimidazolyl-7'-azo) -
benzimidazole
thyl-benzimidazolyl-7'-azo)-
benzimidazol7-amino-5-methyl-4- (5'-me-
ethyl-benzimidazolyl-7'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
zolyl-7'-azo)-benzimidazol7-amino-5-methyl-4- (inda-
zolyl-7'-azo) benzimidazole
zolyl-7'-azo)-benzimidazol7-amino-5-methyl-4- (inda-
zolyl-7'-azo) benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
zolyl-7'-azo)-benzimidazol7-amino-5-methyl-4- (inda-
zolyl-7'-azo) benzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
zolyl-7'-azo)-benzimidazol7-amino-5-methyl-4- (inda-
zolyl-7'-azo) benzimidazole
2,4-dimethoxy-5-chlorbenzol1- (2 ', 3'-oxynaphthoylamino>
2,4-dimethoxy-5-chlorobenzene
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-ethyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
oxy-5'-nitrophenyl-l'-azo)-
benzimidazol7-amino-5-ethyl-4- (2'-meth-
oxy-5'-nitrophenyl-l'-azo) -
benzimidazole
naphthalin2- (2 ', 3'-oxynaphthoylamino>
naphthalene
4-(2'-methoxy-4'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-diethoxy
4- (2'-methoxy-4'-nitro-
phenyl-1 '-azo) -benzimide-
azole
4-(2'-methoxy-4'-nitro-
phenyl-1 '-azo)-benzimid-
azol7-amino-5,6-diethoxy
4- (2'-methoxy-4'-nitro-
phenyl-1 '-azo) -benzimide-
azole
naphthalin2- (2 ', 3'-oxynaphthoylamino) -
naphthalene
nylazobenzimidazol7-amino-2,6-dimethyl-4-phe-
nylazobenzimidazole
4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
4-chlorobenzene
nylazobenzimidazol7-amino-2,6-dimethyl-4-phe-
nylazobenzimidazole
2,5-dimethoxy-4-chlorbenzoll- (2 ', 3'-oxynaphthoylamino) -
2,5-dimethoxy-4-chlorobenzene
4-(3 '-chlorphenyl-1 '-azo)-
benzimidazol
7-Amino-2,6-dimethyl-
4-(3'-chlorphenyl-l'-azo)-
benzimidazol7-amino-2,6-dimethyl-
4- (3'-chlorophenyl-1'-azo) -
benzimidazole
7-amino-2,6-dimethyl-
4- (3'-chlorophenyl-l'-azo) -
benzimidazole
naphthalin
l-(2',3'-Oxynaphthoylamino)-
2-methoxy-4-chlor-5-methyl-
benzol1- (2 ', 3'-oxynaphthoylamino>
naphthalene
l- (2 ', 3'-oxynaphthoylamino) -
2-methoxy-4-chloro-5-methyl-
benzene
Schwarzblack
black
Kobaltkomplexhue
Cobalt complex
Schwarzblack
black
Schwarzblack
black
Claims (5)
Französische Patentschrift Nr. 981 432.Considered publications:
French patent specification No. 981 432.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL273283D NL273283A (en) | 1961-01-12 | ||
| DE1961F0032946 DE1210962C2 (en) | 1961-01-12 | 1961-01-12 | Process for the production of metal-containing, water-insoluble azo dyes |
| CH27162A CH377464A (en) | 1961-01-12 | 1962-01-10 | Process for the production of metal-containing, water-insoluble azo dyes on textile fibers |
| BE612591A BE612591A (en) | 1961-01-12 | 1962-01-12 | Metalliferous azo dyes and their preparation |
| GB128462A GB998522A (en) | 1961-01-12 | 1962-01-12 | Metalliferous water-insoluble benzimidazole bis-azo dyestuffs and processes for their manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1961F0032946 DE1210962C2 (en) | 1961-01-12 | 1961-01-12 | Process for the production of metal-containing, water-insoluble azo dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1210962B DE1210962B (en) | 1966-02-17 |
| DE1210962C2 true DE1210962C2 (en) | 1966-09-15 |
Family
ID=7094872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1961F0032946 Expired DE1210962C2 (en) | 1961-01-12 | 1961-01-12 | Process for the production of metal-containing, water-insoluble azo dyes |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE612591A (en) |
| CH (1) | CH377464A (en) |
| DE (1) | DE1210962C2 (en) |
| GB (1) | GB998522A (en) |
| NL (1) | NL273283A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR981432A (en) * | 1943-04-08 | 1951-05-25 | Francolor Sa | Process for the preparation of azo dyes and their metalliferous comoplexes, and new industrial products resulting therefrom |
-
0
- NL NL273283D patent/NL273283A/xx unknown
-
1961
- 1961-01-12 DE DE1961F0032946 patent/DE1210962C2/en not_active Expired
-
1962
- 1962-01-10 CH CH27162A patent/CH377464A/en unknown
- 1962-01-12 GB GB128462A patent/GB998522A/en not_active Expired
- 1962-01-12 BE BE612591A patent/BE612591A/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR981432A (en) * | 1943-04-08 | 1951-05-25 | Francolor Sa | Process for the preparation of azo dyes and their metalliferous comoplexes, and new industrial products resulting therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| CH377464A (en) | 1964-06-30 |
| BE612591A (en) | 1962-07-12 |
| NL273283A (en) | |
| GB998522A (en) | 1965-07-14 |
| DE1210962B (en) | 1966-02-17 |
| CH27162A4 (en) | 1963-11-30 |
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