Patent GB-921532-A (GB)
Title: New disazo triazine dyestuffs
Inventor: ANDREW HERBERT FRANCIS
IPC: C09B62/08
Filed: 1959-04-22
Abstract: The invention comprises dyes which, as free acids, are of formula <FORM:0921532/IV(a)/1> where A is phenyl or naphthyl and may be substituted by halogen atoms or alkyl or alkoxy groups of not more than 4 carbon atoms or by hydroxy or sulphonic or carboxylic acid groups, R1 is H or alkyl of not more than 6 carbon atoms, X is Cl or Br, Y is amino, aryl, aryloxy, alkylamino, arylamino, sulphoarylamino or carboxyarylamino where the aryl residue has not more than 12 carbon atoms, m is 1 or 2, n is 1, 2, 3, 4 or 5, p is 1 or 2 and B may contain further substituents.  The dyes may be made in conventional fashion by diazotizing an appropriate amine A-N=N-B.NH2 and coupling with the required triazine component, by treating an appropriate disazo amino dye with the necessary dihalo-triazine, or by treating a dye corresponding to the above formula but with Y as halogen with an appropriate compound H.D. where D is any of the above specified values of Y except aryl.  Representative of specified values for A are methyl, butyl and ethoxy and for R1 are ethyl and butyl.  Amongst indicated values of Y are tolyl, phenoxy, di-(b -hydroxyethyl)amino, phenyl- and naphthylamino, hydroxyphenylamino, 2-carboxyphenyl-amino, 3-sulphophenylamino and 3,5-disulphophenylamino.  Examples of substituents for B are sulpho, chloro, methyl, ethoxy and acetyl- and benzyl-amino. Representative of amines corresponding to A are aniline, metanilic acid, 5-amino-2-hydroxybenzoic acid, 2-naphthylamine-8-mono-, 3,6-di- and -3,6,8-trisulphonic acids, 1-naphthylamine-7-sulphonic acid, 1-amino-8-naphthol-3,6-disulphonic acid, 5-chloro-4-methylaniline-2-sulphonic acid, 4-methoxyaniline-2-sulphonic acid, anthranilic acid, 4-sulphoanthranilic acid, 2-ethoxy-1-naphthyl-amine-6-sulphonic acid and 4-sulpho-2-amino-anisole.  Representative of amines corresponding to B are 2-methoxy-5-methylaniline, m-toluidine, m-aminoacetanilide, 4-benzoylamino-2-amino-anisole, 2-amino-4-methoxyphenoxyacetic acid, anthranilic acid, 2-methoxy-1-naphthylamine-6-sulphonic acid and 1-naphthylamine. Amongst components specified which correspond to the naphthol sulphonic acid component are 1-amino-8-naphthol-3,6-disulphonic acid and its 31- or 41-aminobenzoylamino derivatives, 1-N-butylamino-8-naphthol-4,6-disulphonic acid and 1-amino-8-naphthol-3- and -4-sulphonic acids.  Specified triazines include 2-phenyl-, -amino-, diethylamino, -phenylamino-, 21-sulphophenylamino, 31-carboxyphenylamino-, -phenoxy- and -41-hydroxy-31-carboxyphenylamino-4,6-dichloro-1,3, 5-triazine and 2-amino-4,6-dibromo-1,3,5-triazine.  Preferred dyes are those containing a metallizable group in B in the ortho position to the azo bond linking B with the naphthalene nucleus. Hydroxy, carboxy, methoxy and carboxymethoxy are specified metallizable groups. Copper, nickel, cobalt and chromium are specified metals, copper being preferred.  The metal complexes are made in usual fashion by condensing appropriate disazo amino dyes, dihalo triazines and metallizing agents.  Preferably the dye is metallized before reaction with the dihalotriazine.  When Y is not to be aryl the metal complexes may also be made by treating appropriate complexes of dihalotriazine disazo dyes with a compound of formula H.D. where D is as above defined.  The dyes and their metal complexes colour cellulosic textile materials and are preferably used in conjunction with a treatment with an acid-binding agent vide Specification 797,946.  Reddish-blue to greenish-blue shades are obtained.  A preferred class of dyes are the copper complexes of dyes of formula <FORM:0921532/IV(a)/2> where B, X, Y and n are as above defined, A1 is a phenyl or naphthyl residue having at least one sulphonic acid group, 21 is OH or OMe and one T is SO3H and the other H. Preferably X is Cl, Y is mono- or di-sulphoanilino residue and n is 1.  Numerous examples are provided of the preparation of the dyes and their metal complexes and their use in colouring cellulosic materials. Specifications 838,728 and 847,635 also are referred to.