Patent GB-876092-A (GB)
Title: New disazo-dyestuffs containing triazine residues and processes for their manufacture and application
IPC: C09B62/08
Filed: 1957-09-13
Abstract: The invention comprises dyes of formula:-  <FORM:0876092/IV(c)/1> where D is the residue of a diazo component containing an azo group and at least one watersolubilizing group, R a benzene residue, if desired containing sulphonic acid groups, and X is a 2-halogen- 4-amino-1, 3, 5-triazine residue attached by way of its 6-position. The dyes may be made by conventional diazotization and coupling processes or by treating appropriate dyes with a trihalotriazine and ammonia or an appropriate amine.  In the latter type of preparation the dihalo-triazine dye may be isolated before reaction with the amino compound or the reaction product of the halotriazine with the amino compound before reaction with the dye.  Preferably the halotriazine is a chlorine derivative; the amino compound is ammonia or a primary mono-amine which contains at most 12 C atoms, R contains SO3H #sto the NH group connecting R and X and D contains an SO3H group.  Particularly preferred are compounds where D is R1-N=N-R2 where R2 is a benzene residue with the azo groups in the m- or p-position to each other and R1 is a benzene, naphthalene or pyrazolone residue containing an SO3H group and the amine group attached to the triazine residue is NH2 or derived from an aliphatic primary amine of at most 6 carbon atoms or an arylamine.  Indicated as watersolubilizing groups are COOH and SO3H.  D may contain further substituents e.g. amino, hydroxy, nitro and halo groups, and may also be a naphthylazo-naphthalene or -pyrazolone residue. Representative of amino compounds used for reaction with the halotriazines are ammonia, methyl-, cyclohexyl- and dimethylamines, aniline, morpholine, b -chlorethylamine, ethanolamines, acetamide, thiourea, hydrazine, toluenesulphonamide, glycocol, aminocarbonic acid esters, aniline- 4-sulphonic and -carboxylic acids, b -amino-ethane sulphonic acid and naphthylamine sulphonic acids.  Representative of specified naphthol sulphonic acid coupling component residues are 2-(41-aminophenylamino)-5-naphthol- 7-mono- and 31, 7- di-sulphonic acids.  Indicate as components corresponding to D are 4- amino- 1, 11- azobenzene- 3, 41-disulphonic acid and dyes made by coupling coupling components containing an amino group with diazo compounds from aniline-, naphthylamineaminopyrene- and -chryseneaminonaphthol- and aminophenol-sulphonic acids, e.g. by coupling diazotized nitranilies, toluidines, nitramino-benzoic acids and naphthylamines with cresidine, 3-acylamino-anilines, a -naphthylamine, 2-amino- 8-naphthol- 6-sulphonic acid and 8-amino- 1-naphthol- 3, 6-disulphonic acid.  Other components corresponding to D which are indicated are those obtained by coupling diazotized monoacyl derivatives of aromatic-diamines with azo components containing an aromatic-hydroxy or keto-methylene group with subsequent hydrolysis of the acylamino group e.g. hydrolysis of amino-azo dyes made from phenols, naphthols, 5-pyrazolones, barbituric acids, hydroxyquinolines, b -keto carboxylic acid derivatives and diazotized monoacyl-diamino-benzenes and -stilbene disulphonic acids.  The dyes are particularly useful for colouring cellulosic materials p  especially when combined with an alkaline treatment.  Dyes which contain metallizable groupings may be metallized on the fibre. Examples are provided of the preparation of the dyes and their use in colouring cellulosic materials in blue shades.  Specifications 797,946 and 838,337 are referred to.