Patent GB-762844-A (GB)
Title: Polyazo dyestuffs
IPC: C09B31/22
Filed: 1954-12-20
Abstract: The invention comprises dyestuffs of formula <FORM:0762844/IV(b)/1> where R1 and R2 are benzene or naphthalene residues free of hydroxy, nitro and amino groups and together have 2 sulphonic acid groups, R1 containing at least one sulphonic acid group, R3 is a benzene residue free of hydroxy, nitro and amino groups, azo is para both to -N=N- and -NH-CO- and one V is H or halogen or an alkyl or alkoxy group, and the other is <FORM:0762844/IV(b)/2> where W is an arylamino group and N is 1 or 2 and is preferably <FORM:0762844/IV(b)/3> where W1 or W2 is H and the other is an arylamino group.  They are made by diazotizing a compound corresponding to the first of the above formulae while the other V is an amino group and coupling with an appropriate arylaminonaphthol-sulphonic acid.  The aminobenzoylaminodisazo compounds are made by condensing appropriate aminodisazo compounds and nitrobenzenecarboxylic acid halides with subsequent reduction of the nitro group.  The aminodisazo compounds are made in conventional fashion from appropriate components.  Amines indicated as components corresponding to R1 are aminobenzene mono- and di-sulphonic acids, amino-methyl- and halogen-benzene sulphonic acids and amino-naphthalene mono- and di-sulphonic acids.  Specified amines as components corresponding to R2 and R3 (restricted to anilines) are 1-amino -2- and -3-methyl- and -methoxy-, -2, 5-dimethyl-, -dimethoxy- and -diethoxy-, and -2-methoxy-5-methyl-benzenes, 1-amino-3-acetylamino-benzene and 1-naphthylamine and its 6- and 7-sulphonic acids. Aminobenzenedisulphonic acid, e.g. 4-amino-1, 11-azobenzene-3, 41-disulphonic acid are particularly mentioned as azoamino components for use in the preparation of the aminodisazo compounds.  Specified acid halides are 3- and 4-nitro-, 3-nitro-4-methoxy-, 3-methyl-4-nitro- and 3-chloro-and -bromo-4-nitro-benzyl chloride and the corresponding benzoyl bromides.  Specified arylaminonaphthol sulphonic acids are 1-acetyl- and -benzoyl-amino-5-naphthol-7-mono- and -8-naphthol-3, 6-di-sulphonic acids, preferred being 2-acetyl-, -propionyl-, -crotonyl-, -benzoyl-cinnamoyl -(31- and 41-amino, 31-methyl-41-aminoan 31-amino-41-methoxy)-benzoyl-, -carbomethoxy-, - carboethoxy-, - carbopropoxy-, carbobutoxy- and -carbo-(21-ethoxy)-ethoxy-amino-5-napthol-7-and -8-naphthol-6-sulphonic acids and 5-naphthol-7-sulphonaphthalene - 2 - carbamic acid - (41 - acetylamino)-phenylamide. Cotton and regenerated cellulose fibres are dyed in orange, red and brown shades.  When an aminobenzoylaminonaphthalene sulphonic acid is used as end azo component the final triazo dyestuffs may be dyed, diazotized in the fibre and coupled with azo components, e.g. 2-naphthol.  Examples and a table illustrate the preparation of the dyestuffs and their use in dyeing cotton, components and corresponding to R1 are aniline-4-mono- and -2, 5-disulphonic acids, 1-amino-2, 4-dimethyl-6-sulphonic acid, 1-amino-2-chlorobenzene-4-sulphonic acid and 2-naphthylamine-4, 8- and -6, 8-di-sulphonic acids, aniline is an additional component used to those listed above corresponding to R3 and additional benzoyl chlorides used to those listed above are 3-nitro-4-ethoxy- and 3-ethyl- and -methoxy-4-nitro-benzoyl chloride.