Patent GB-798746-A (GB)
Title: New chromium-containing monoazo-dyestuffs and process for making them
IPC: C09B45/16
Filed: 1955-01-14
Abstract: The invention comprises complex chromium compounds which contain bound in complex union to one atom of chromium two different mono-azo dyestuffs of which one is of formula <FORM:0798746/IV (b)/1> in which R is a benzene residue bound to the azo linkage in o-position to the COOH group and is free from groups imparting solubility in water and R1 is a benzene residue which is free from groups imparting solubility in water, is bound in the 1-position to the pyrazolone ring and contains in the 2-position a substituent not imparting solubility in water, and the other of which dyestuffs is an o-carboxy, o1-hydroxymonoazo dyestuff free from sulphonic acid groups or an o,o1-dihydroxy-monoazo dyestuff free from sulphonic or carboxylic acid groups.  They are made by treating appropriate dyestuff mixtures with chromium yielding agents, including a 1,1-complex of the second dyestuff by usual methods.  Dyestuffs of the above formula are made in the usual fashion by coupling appropriate diazotized anthranilic acids and pyrazolones.  The acids and pyrazolones may contain substituents such as nitro, alkoxy and halogen groups, the additional substituents in the pyrazolones being preferably in the 61 position.  The pyrazolones may also contain alkyl groups. Specified pyrazolones are 1-(21-nitro-, 21,41- and 21,61-dimethyl, 21,61- and 21,51-dichloro-, 21-methyl - 61 - chloro - or - methoxy -, and especially 21-methyl-, -ethyl-, -bromo-, -chloro-and -methoxy-phenyl)-3-methyl-5-pyrazolones.  Specified acids are 4- and 5-nitro-, 4-methoxy-and 5 - chloro - 2 - aminobenzene - 1 - carboxylic acids and anthranilic acid which is preferred. Advantageously the second dyestuff is of formula HO(OC)n-1-R-N=N-R1, where n is 1 or 2, R is a benzene residue free from So3H or COOH groups and is bound to the azo link o-to -(CO)n-1-OH and R1 is the residue of a coupling component free from SO3H and COOH groups bound to the azo link vicinal to an OH group.  The second dyestuffs may be prepared by conventional methods from appropriate diazo and coupling components.  Specified diazo components are anthranilic acid, 6-acetylamino-4-nitro-, 6-nitro-4-acetylamino-, 4- and 5-nitro-, 4,6-dinitro- and -dichloro-, 4-nitro-6-chloro-and 4-chloro-5-nitro-2-aminophenols, 2 - aminophenol - 4 - and - 5 - methyl - and phenyl-sulphones and sulphonamides.  Specified coupling components are 5-chloro- and 5,8-dichloro-1-naphthols, 2-naphthol, 6-bromo- and -methoxy-2-naphthols, 1-acetyl-, -n-butytrl- and -benzoyl-amino-7-naphthol, 1-naphthol-3,6-di-(sulphonic and methyl-amide) and advantageously 1-phenyl- and -(21-, 31- and 41-chlorophenyl) - 3 - methyl - 5 - pyrazolones, 1 - phenyl-5-pyrazolone-3-carboxylic acid amides and 5-pyrazolone - 3 - carboxylic acid - n - butylamide.  The dyestuffs dye materials such as silk, leather and wool and fibres of super-polyamides and -polyurethanes and polyvinyl alcohol from weakly acid, neutral or weakly alkaline baths.  Examples are provided of the preparation of the metal complexes and their use in dyeing wool in yellow, red and green tints, the components used in the preparation of the first dyestuff being selected from those specified above and those used for the second dyestuffs being chosen from those specified above with the addition of 3,4-dimethylphenol as a coupling component and 4-methoxy-2-aminophenol-5-sulphonamide and 2-aminophenol-4-ethyl sulphone and -sulphon-methylamide as diazo components. Specifications 637,404 and 797,046 are referred to.