Patent GB-846765-A (GB)
Title: New colouring matters containing triazine rings and their use
Inventor: BARKER PETER WILLIAM
IPC: C09B62/04
Filed: 1957-08-07
Abstract: Cyanuric chloride is condensed with phenols containing negative substituents to form 2,4 di(substituted phenoxy) 6-chlorotriazines. Sodium salts are also described.  Substituents specified are nitro and sulphonic groups.ALSO:The invention comprises water-soluble dyestuffs of the general formula:  <FORM:0846765/IV (c)/1> where X represents the radical of a coloured compound which is attached to a nitrogen atom which is also attached to the carbon atom of the triazine nucleus.  Y represents a negatively substituted aryloxy or a substituted or unsubstituted arylthio grouping, and Z represents a substituent connected to the triazine nucleus through carbon, nitrogen, oxygen or sulphur.  The solubilising groups may be present in any of the groups X, Y or Z. The nitrogen atom in X which is attached to a carbon atom, may be attached by one link in which case the third substituent attached to the nitrogen atom may be for example, hydrogen, alkyl, aralkyl or cycloalkyl, or by two links, when it forms part of a saturated heterocyclic ring.  The dyestuffs of the invention may be prepared by reacting together a triazine containing more than one halogen atom, a negatively substituted hydroxy aryl compound, or a substituted or unsubstituted mercaptoaryl compound and a compound which is coloured and contains one or more amino or mono substituted amino groups, in such proportions and under such conditions that no halogen atoms are left attached to the triazine nucleus.  Amongst examples given of suitable starting materials are the following triazines, cynanuric chloride and bromide, 4 : 6 dichlorotriazines substituted in the 2 position by phenyl, methyl, methoxy, -beta chloroethoxy, amino, anilino, phenoxy, ethoxy, p-methylphenoxy, and methyl-, dimethyl-, diethyl-, isopropyl- or cyclohexyl amino, and chloro- and methyl-aniline groups; the following negatively substituted hydroxyaryl compounds, phenol sulphonic and disulphonic acids, nitrophenol, chlorophenol and methylphenol sulphonic acids, and phenol carboxylic acids; the following mercapto compounds, thiophenol, thiocresol, p-nitro and p-chloropthiphenol and thiophenol and thionaphthol sulphonic acids. Amongst suitable monosubstituted amino groups which may be present in the compounds used in the above process of the invention are for example alkylamino, aralkylamino groups as well as for example b -hydroxyethyl, b -sulphoethyl, b -sulphatoethyl, b -chloroethyl, gamma-chloro-beta-hydroxy propylamino, and beta-chloroethyl-amino groups.  Coloured compounds which may be used in the above process are nitro, azo, thiazole, azoxy stilbene, pyrazolone, hydrazone, di- and triaryl methane, acridine, oxyazine, thiazine, azine, indigoid, anthraquinone, amino-anthraquinone and phthalocyanine dyestuffs.  The process is preferably carried out in a liquid medium, and is preferably carried out in two stages, first reacting together the triazine and one of the two other reactants, and then treating the product so obtained, after isolation and purification if desired, with the third reactant.  Alternatively if an azo group is present in the desired compound a diazotisation and coupling reaction may be used.  The dyestuffs may be used for dyeing cellulosic textile materials, especially in conjunction with an alkaline agent. Examples are given of the preparation of many dyestuffs and the dyeing and printing of cottons.