Patent GB-876923-A (GB)
Title: New azo-dyestuffs containing a monohalogenated triazine nucleus, their manufacture and use
IPC: C09B62/08
Filed: 1957-09-16
Abstract: The invention comprises water-soluble azo dyes which contain at least two substituents selected from carboxylic and sulphonic acid groups and, in addition, a 2-halo-4-amino-1, 3, 5-triazine residue bound in the 6-position via an amino bridge to the residue of a benzenic diazo-component and of which the amino group in the 4-position of the triazine nucleus is NH2 or the residue of an amine which contains at most 12 carbon atoms and, if it contains an aromatic ring, also has a carboxylic and/or sulphonic acid group.  The dyes may be made by condensing appropriate aminoazo dyes containing the required dihalotriazine residue with ammonia or a required amine, by condensing appropriate aminoazo dyes and dihalo-triazine components, or from appropriate triazine-diazo components and the required coupling component. Preferred are dyes with at least two sulphonic acid groups and of formula:-  <FORM:0876923/IV(c)/1> where Y is an arylamino group or especially NH2, R is a residue of the benzene series, especially monocyclic, containing a sulphonic acid group and A is a coupling component residue containing a carboxylic or sulphonic acid group especially of a 5-pyrazolone bound in the 4-position to the azo link and containing a sulphonic acid group or of an oxy- or aminonaphthalene sulphonic acid, particularly of an N-acylaminonaphthol mono- or di-sulphonic acid.  The diazo component residue may contain methyl, alkoxy, chloro or nitro substituents and may be a phenylene or a bicyclic residue which may contain an azo link.  Preferably the dyes contain more than one of the above acid watersolubilizing groups per azo link. Representative of indicated diazo-components are monoacyl derivatives of 4, 41-diamino-diphenyl-3-sulphonic acid, 4, 41-diaminostilbene-2, 21-disulphonic acid, 4-(41-aminobenzoylamino)-1-aniline-2-sulphonic acid, 1, 3-diaminobenzene, 1, 4-diaminobenzene-2-carboxylic and 3-sulphonic acids and 2-methoxy-1, 4-diaminobenzene-5-sulphonic acid. Representative of indicated coupling components are b -keto-carboxylic acid esters or amides, e.g. acetoacetic acid arylides, 1-phenyl-3-methyl-5-pyrazolone and its 41-sulphonic acid, 5-pyrazolone-3-carboxylic acid amide, barbituric acids and oxyquinolines, phenols e.g. p-cresol, 4-methyl-2-acetylamino-1-phenol and salicylic acid, naphthols e.g. b -naphthol, a -naphthylamine, 2-naphthol-6-sulphonamide, 1-naphthol-8-sulphonic acid, 1, 8-dioxynaphthalene-3, 6-disulphonic acid, 2-naphthylamine-6-sulphonic acid, 1-amino-8-naphthol-4, 6-disulphonic acid, and N-aryl-aminonaphthol sulphonic acids containing as acyl residue e.g. propionyl, chloracetyl, nitrobenzoyl, 31-aminobenzoyl, ethane p sulphonyl, chlorobenzene sulphonyl and carbethoxy or a residue derived from a cyanuric acid, and coupling components e.g. 5, 51-dioxy-2, 21-dinaphthylurea-7, 71-disulphonic acid, which may be coupled twice with diazo components and monoazo dyes obtained from diazo-compounds of the benzene or naphthalene series e.g. naphthylamine, aniline sulphonic acids and aminobenzoic acids, and coupling components, e.g. 2-amino-5-naphthol-7-sulphonic acid and 8-amino-1-naphthol-3, 6-disulphonic acid.  Representative of specified amino compounds are ammonia, methylamine, diethylamine, cyclohexylamine, b -chlorethylamine, g -methoxy-propylamine, ethanolamine, butyric acid amide, thiourea, toluenesulphonamide, glycine, methyl aminocarbonate, ethyl aminoacetate, aminoacetamide, phenylhydrazine sulphonic acids, thiosemicarbazide, 1-aniline-2, 5-disulphonic acid, naphthylamine disulphonic acids, amino-diphenyl sulphonic acids and N-methylaminoethane sulphonic acid.  The dyes are particularly of use for cellulosic materials especially when the colouring process includes an alkaline treatment.  Dyeings from metallizable dyes may be after-treated with metal-yielding agents. Chromium, nickel and copper are specified metals the last-named being preferred.  Examples are provided of the preparation of the dyes and their use in colouring cellulosic materials in blue, red and yellow shades. Specifications 209,723, 299,331, 797,946, 826,405, 852,120, 863,155 and 864,227 are referred to.