Patent GB-872249-A (GB)
Title: New monoazo-dyestuffs derived from cyanuric halides and processes for their manufacture and application
IPC: C09B62/08
Filed: 1957-09-13
Abstract: The invention comprises monoazo dyes containing at least two acid water-solubilizing groups and a 2-halogen-4-amino-1, 3, 5-triazine residue having in the amino group in 4-position at most 12 carbon atoms, which residue is bound by way of its 6-position through an amino bridge in b -position of the residue of a b -naphthylamine sulphonic acid which is attached to the azo group in a position vicinal to a hydroxyl group.  The dyes may be made by reacting together in any order of succession a 2, 4, 6-trihalogen-1, 3, 5-triazine, an appropriate aminoazo dye, and ammonia or the required amine.  The dyes may also be made by coupling a diazo compound with a b -aminonaphthol sulphonic acid containing the b -triazine substituent and, if the amine is aromatic, also an acid water-solubilizing group.  Carboxyl and sulphonic acid are the defined acid water-solubilizing groups. Preferably the triazine residue is linked to the dye molecule via a bridge of formula:- <FORM:0872249/IV(c)/1> where n is an integer and the diazo moiety has a carboxyl or sulphonic acid group the amine residue being derived from an aliphatic amine containing 1-6 carbon atoms or an aromatic amine containing a sulphonic or carboxylic acid group.  Particularly preferred are dyes of formula:-  <FORM:0872249/IV(c)/2> where X is NH2 or the above indicated amino group which, if aromatic, has a carboxyl or sulphonic acid group, n is 1-3, D is a diazo component residue, R is an aryl, preferably benzene, residue attached to the <FORM:0872249/IV(c)/3> residue directly or via CO or SO2, m is 1 or 2 and an acid water-solubilizing group is in at least one of D, R, or X.  D may be a phenyl group which may contain methyl, alkoxy, chloro or nitro substituents, or may be a naphthalene or diphenyl residue. Representative of specified b aminonaphthol sulphonic acids are:-2-aminoand -N-methylamino- 8-naphthol- 6- and 2(41-aminobenzoylamino)- 5-naphthol- 7-monoand 2-(41-aminophenylamino)- 5-naphthol-31, 7-di-sulphonic acids. Indicated as compounds from which the diazo moiety may be derived are:-amino-benzene, -naphthalene, -pyrene and chrysene sulphonic acids and amino-phenol and -naphthol sulphonic acids representative of those specified being aniline- 3-sulphonic or carboxylic acid, 2-amino- 1-methoxybenzene- 4-sulphonic acid, 3-amino- 2-hydroxybenzoic acid- 5-sulphonic acid, 2-aminophenol- 4-sulphonic acid, 5-acetyl-amino- 2-aniline- 1-sulphonic acid, 5-benzoylamino- 2-aniline- 1-carboxylic acid, 1- and 2-naphthylamine- 4-sulphonic acid, aniline2, 5- di- and 2-naphthylamine-5, 7- di-sulphonic acids, 1-(31-aminobenzoyl)-aminobenzene- 3-sulphonic acid, 3-aminopyrene 8-mono- and 5, 10-di-sulphonic acids, 4-nitro- 41-aminostilbene-2, 21-disulphonic acid, O-acyl derivatives of 1-amino- 8-naphthol-3, 6-disulphonic acid and dehydrothiotoluidinemono- and di-sulphonic acids. Representative of compounds from which the amine residue is derived are:-ammonia, methyl-, diethyl-, isopropyl and cyclohexylamines, piperidine, b -chlorethyl- and g -methoxypropylamines, ethanolamines, butyric acid amide, thiourea, hydrazine, toluene sulphonamides, glycocol, ethyl esters of aminocarbonic and aminoacetic acids, aminoacetamide, aniline- 2-mono- and -2, 5- di-sulphonic acids, aniline- 4-carboxylic acid and N-methylamino ethane sulphonic acid.  The dyes are of particular use on cellulosic materials especially when used in cobjunction with an alkaline treatment. Dyes containing metallizable groupings e.g. #s, #s1-dihydroxyazo or #s-hydroxycarboxy groups, may be metallized, preferably with copper or nickel compounds.  Examples are provided of the preparation of the dyes and their use in colouring cotton in red or orange shades.  Specifications 785,120, 797,946, 838,337 and 838,340 are referred to.