Patent GB-961302-A (GB)
Title: Improvements in or relating to dis- and poly-azo dyestuffs
Inventor: STEINEMANN WILLY
IPC: C09B50/00
Filed: 1960-07-08
Abstract: The invention comprises dyes of formula <FORM:0961302/C4-C5/1> where R1 and R2 are radicles of diazo components, X1 is a metallizable substituent o to N2, X2 is H or a metallizable substituent o to N2, R3 is an hydrocarbon radicle which may be substituted, m is 0, 1 or 2 and X3 is <FORM:0961302/C4-C5/2> and their metal complexes.  The dyes are made by coupling one mol. of a hydrocarbon which has n radicles of formula H2C(2)SO2-, where Z is COOH or a group convertible thereto at pH 5-12 and n is 1, 2 or 3 with 2n mols. of one or more diazo compounds, of which at least n mols. have a metallizable substituent o to the diazo group, and, if desired, metallizing in substance or on the fibre.  The dyes may contain amino, hydroxyl or thiol groups, which contain reactive hydrogen atoms, or substituents readily convertible to such groups e.g. nitro or halogen groups, combined directly, or through a divalent radicle, as well as other substituents. Specified groups for conversion to COOH are carboxylic ester or amide or nitrile.  The hydrocarbon residue attached to the group, or groups, H2C(2)SO2- may be aliphatic e.g. methyl, hexyl, cycloaliphatic e.g. cyclohexyl, aromatic e.g. phenyl, naphthyl and preferably is non-polymerizable.  Conventional diazo components are used e.g. amines of the aromatic and heterocyclic-aromatic series, and they may contain substituents such as SO3H, COOH, SO2NH2, which may be mono- or di-substituted, and sulphonyl, alkyl, alkoxy, aryl, nitro, fluorine, chlorine and bromine groups. Indicated metallisable groups are hydroxy, carboxy, amino, sulphamide and alkoxy groups. Diazo and couplign components may contain azo groups and may be metallizable or metallized.  They may also contain substituents which enable them to be converted into other polyazo dyes by azo coupling. Representative of divalent radicles indicated as linking members are CH2, -CH2-C(Me)H, <FORM:0961302/C4-C5/3> <FORM:0961302/C4-C5/4> <FORM:0961302/C4-C5/5> <FORM:0961302/C4-C5/6> , where R1 is H, alkyl, hydroxyalkyl, cycloalkyl, aralkyl or aryl and R11 is acyl and the aliphatic chains may contain the groups containing hereto atoms. Copper, cobalt, chromium, zinc and nickel are specified metals. The dyes, when water-soluble, may be used to colour textiles e.g. wool, silk, polyamide and polyterephthalic acid glycol esters, and leather. Water-solubilizing groups specified are COOH, SO3H, SO2NH2 and sulphonyl.  When insoluble in water the dyes may be used in a disperse process to colour artificial fibres, plastics and lacquers. High molecular weight dyes, as metal complexes formed in substance or on the fibre, may be used to colour acetylated, natural and regenerated cellulose and leather. Examples are provided of the preparation of the dyes, and their metal complexes, and the use of the latter in colouring nitrogenous fibres in red, green and blue tints.  Representative of diazo components used in the examples are 2-aminophenol - 4 - or 5 - sulphonic acid phenyl-, amyl -, cyclohexyl, 21 - hydroxyethyl, 31-methoxy - propyl -, o - carboxyphenyl - and dimethyl - amino - propyl - amides, 2 - amino phenol - 4 - sulphonic acid morpholide, 2 - amino - 4 - nitro -, chloro - or tert - butylbenzene, 2 - carboxyaniline, 2 - amino - 1 - carboxy-5-sulphonic acid phenylamide, 1-amino-2-carboxy - 4 - sulphobenzene and 1 - amino - 5 -carbethoxyamino - 2 - phenol, and representative of coupling components used are 4-methylsulphonylamino -, 3 - acetamino -, 2 - methyl-4 - benzoylamino -, 4 - pyrrolidonyl -, 2,5 dimethoxy - 4 - acetamino - and 3 - carboxybenzene-sulphonyl acetic acids, benzo - sulphonyl acetic acid, 6-acetamino-naphthalene-2-sulphonyl acetic acid, napthalene-(1)-sulphonyl acetic acid-4-sulphonic acid and n-butyl and cyclohexyl-sulphonyl acetic acid and 1-acetamino-naphthalene-3,6-disulphonyl acetic acid.