Patent GB-766015-A (GB)
Title: Improvements in or relating to disazo dyestuffs
IPC: C09B31/08
Filed: 1954-07-07
Abstract: The invention comprises dyestuffs of formula <FORM:0766015/IV(b)/1> where R is a benzene residue containing a water-solubilizing group and X is halogen, OH, NH2 or the residue of a primary or secondary amine.  They are made by condensing 1 mol of a triazine compound which contains 3 replaceable halogen atoms bound to carbon atoms, e.g. cyanuric trichloride, with 1 mol of the aminodisazo compound made by diazotising 4-amino-1, 11-azobenzene- 3, 41-disulphonic acid and coupling in the 6 position of 2-amino-5-naphthol-7-sulphonic acid and with 1 mol of an appropriate aniline derivative and, if desired, with 1 mol of ammonia or a primary or secondary amine, the condensing operations being effected in any desired sequence.  Alternatively they may be made by coupling diazotised 4-amino-1, 11-azobenzene-3, 41-disulphonic acid with a compound of formula <FORM:0766015/IV(b)/2> where R and X are as above and if X is halogen it may be replaced as before.  Specified water-solubilizing groups are SO3 H, COOH, SO2NH2 which may be N-substituted and alkylsulphonyl groups.  Condensations are advantageously effected in an aqueous medium in the presence of an acid-binding agent such as lithium sodium or potassium hydroxides, carbonates, bicarbonates and acetates.  Where the water-solubility of the aniline derivative is slight it may be added in a solvent such as acetone.  The aminodisazo compound is made by coupling diazotized 4-amino-1, 11-azobenzene-3, 41-disulphonic acid with a 2-acylamino-5-naphthol-7-sulphonic acid in neutral to weakly acid medium, separating the byproduct coupled in the 8-position, and saponifying the acylamino group in the derived intermediate dyestuff. The triazine used in the second modification is made by condensing 1 mol of an appropriate triazine compound which contains three halogen atoms with 1 mol of 2-amino- 5-naphthol-7-sulphonic acid and 1 mol of the required aniline derivative and, if desired, replacing a third halogen atom, if present by an appropriate amine or OH residue. Preferred anilines are aniline-3- and 4-sulphonic acids, -sulphononamides and carboxylic acids and 1-amino-3- and 4-methylsulphonylbenzenes. The anilines may contain further substituents e.g. halogen atoms and alkyl groups.  Primary or secondary amines used may contain substituents such as halogen atoms or hydroxyl groups, and they may be aliphatic carbocyclic or heterocyclic, those specified being the above anilines and methyl-, dimethyl-, ethyl-, 2-hydroxy-ethyl-, di-(2-hydroxyethyl)-, propyl-, 3-hydroxy-propyl-, butyl-, amyl-, hexyl-, benzyl-, and cyclohexyl-amines, morpholine, aniline, 3-and 4-chloro - and - methyl-anilines, 4-methoxy - and - acetylamino-anilines, 1-amino-dimethylbenzenes, N-methyl - and - ethyl - aniline and 1- and 2-napthylamine sulphonic acids.  A preferred series of dyestuffs are those where R is the residue of an aniline sulphonic acid or sulphonamide and/or X is a residue of an aminobenzene. The dyestuffs dye cotton and regenerated cellulose films in scarlet to red shades. Examples are provided of the preparation of the dyestuffs and their use in dyeing cotton and regenerated cellulose fibres primary and secondary amines used apart from those specified above being octylamine, 4-ethylamine and aniline-3-sulphonic acid methylamide and additional compounds corresponding to R being aniline 3-dulphonic acid methyl-and dimethyl-amides and 4- (21hydroxy) -ethyl-and - (21-carboxy) - phenyl-amides and 1 - amino - 3 - phenyl - sulphonyl-benzene.