Patent GB-877178-A (GB)
Title: New polyazo triazine dyestuffs
IPC: C09B62/08
Filed: 1958-11-19
Abstract: The invention comprises polyazo dyes which contain at least one acid water-solubilizing group and a halogenated-s-triazine radical attached through N to a middle component.  The dyes may be made by treating an appropriate aminoazo dye with a cyanuric halide or dihalo-s-triazine and, if desired, treating the product with ammonia or a primary or secondary amine or a hydroxy or mercapto compound. Bis-, tris- and tetra-azo dyes are described, bis-azo dyes being preferred.  The dyes may contain metallizable groupings e.g. #s, #s1-dihydroxy-, #s-hydroxy-#s1-carboxy-and #s-hydroxycarboxy groups. Chromium, nickel, cobalt, iron and copper are specified metals the last-named being preferred.  Each middle component may contain a halo-s-triazine residue and the end components may also contain such a residue.  Sulphonic and carboxylic acid are specified acid groups. Advantageously the dyes contain at least one acid group per azo link. Preferably the azo groups in the middle component are in the 1, 3 or 1, 4 positions and, when a polycyclic e.g. a diphenyl residue, are in 4, 41-relationship.  Representative of specified cyanuric halides and dihalo-s-triazines are cyanuric bromide and chloride, 2, 4-dichloro-s-triazine, 2, 4-dichloro-6-methyl-s-triazine and 2, 4-dichloro-6-nitrophenyl-s-triazine.  Preferably the dihalo-s-triazine is a primary condensation product of a cyanuric halide with ammonia or a primary or secondary amine or hydroxy or mercapto compound and preferably has no colour.  The starting polyazo dyes may be made (1) from a twice coupling middle component which contains an acylatable amino group or a group convertible thereto e.g. m-phenylene diamine, m-aminophenol and m-toluylene diamine, and they are coupled with diazo components such as arylamines of the benzene, naphthalene, diphenyl, diphenylamine, diphenyloxide, diphenyl sulphide, stilbene, diphenyl ethane, diphenyl methane, pyrene or chrysene series and diazo components containing azo groups may also be used; (2) by coupling a dizotized aminoazo dye, where coupling component contains an acylamino or nitro group, with a coupling component and converting the acylamino or nitro group into an amino group, representative of specified first coupling components being 4-methoxy-3-aminopropionanilide, 4-benzpylamino-2-aminoanisole, 4-acetylamino- 2-aminobenzoic acid and 3-(41-nitrobenzoylamino)-aniline and indicated for second coupling components are phenols, naphthols, naphthylamines, aminonaphthols, acylaminonaphthols, anilines, N-alkylated anilines, acetoacetarylides, pyrazolones and barbituric acids and (3) a tetrazotized aromatic diamine which contains an acylamino or nitro group is coupled with two mols of the same or different coupling components and the acylamino or nitro group is converted to an amino group, tetrazo components specified including 2-nitrobenzidine, 4-acetylamino- 6-nitroaniline, 6-nitro-4, 41-diamino-3, 31-dimethoxydiphenyl, 4, 41-diamino- 2-acetylamino-1, 11-azobenzene and 2-nitro-4, 41-diamino-diphenylmethane.  The dyes colour nitrogenous materials e.g. wool, silk and nylon and cellulosic materials such as cotton, linen and viscose rayon.  Colouring cellulosic materials is advantageously effected in conjunction with an alkaline treatment as in Specifications 797,946 and 820,470. Numerous examples are provided of the preparation of the dyes and their use in dyeing processes to give shades of red, blue, yellow, green and brown.  Specification 842,933 also is referred to.