Patent GB-862374-A (GB)
Title: Improvements in or relating to monoazo dyestuffs and their metal complex compounds
IPC: C09B45/14
Filed: 1958-07-24
Abstract: The invention comprises dyes of formula:-  <FORM:0862374/IV(c)/1> where B is a coupling component residue, z is a phenolic or enolic OH group or a primary or secondary amino group in #s-position to the azo group, v is a metallizable group or one convertible thereto during metallization, x is 0 or a simple link, n is 1 or 2 with the proviso that when it is 2 the bracketed acylamino group appears once in the diazo and once in the coupling portions of the molecule and y for a sulphonamido, amino-sulphonamido, carboxylic acid amido, carbamic acid ester or urea group linked through the amino nitrogen atom with "alkylene," and A may contain substituents.  The invention also includes metal complexes of the above dyes (excluding cobalt dyes containing a carboxyl group #sto the azo group) and complexes of metallizable mixtures containing at least 50% of the above dyes.  The products are made in conventional fashion by coupling an appropriate diazotized aniline derivative with the B component and, if desired, metallizing.  For phenolic or enolic components coupling is preferably effected at 0-10 DEG C. in an alkaline medium and, for amine components, at 10-20 DEG C. in a weakly acid medium. Appropriate mixtures of diazo and/or coupling components may be used. Metallization may be effected in substance or on the fibre 1, 2-complexes being obtained.  Two or more monoazo dyes may be simultaneously metallized.  Chromium and cobalt complexes are preferred, the latter, however, being derived only from phenolic or enolic coupling components or components convertible thereto during metallization.  Preferred complexes are those of dyes of formula:- <FORM:0862374/IV(c)/2> where S is Cl, NO2 or SO2NHPh, t is H or Cl and R is an alkyl group of up to 4 carbon atoms, a mononuclear aryl group or a di-(lower alkyl)-amino group with the acylamino group in the 5 or 8 position.  Preferably v is OH, OMe or COOH but may also be halogen.  Indicated coupling components are phenols, naphthols, alkyl-, cycloalkyl-, aralkyl- and aryl-amino-naphthalenes, naphthylamines, 1-aryl-3-methyl-5-pyrazolones and acylacetylamino-alkanes, -benzenes and -naphthalenes.  Examples of substituents for A and the coupling components are halogen atoms and nitro, actylamino, benzoylamino, carboxy, carbethoxyamino, ethyl, methoxy, sulphonic acid and its amide and monoand di-methyl-amides, 31-hydroxy- and -methoxypropyl-amides and -phenyl- and -methyl- and -(21-carboxy)-phenyl-amides, methyl sulphonyl and NHCOx alkylene-y groups, the latter being preferred.  The metal-free dyes dye wool, silk, leather and synthetic polyamide fibres by the one-bath and after-chroming processes in red, yellow, green, blue, violet, grey, brown and black shades.  The metal complexes dye the above materials from a neutral or weakly-acid bath in similar shades.  Cotton, polyacrylonitrile, polyester and acetate fibres may be reserved upon after-treatment of dyeings with hydrosulphite.  Dyes, soluble in organic solvents, may be used to colour lacquers, plastic materials and masses for spinning into fibres.  Examples are provided of the preparation of the dyes, their complexes and mixtures thereof and their use in dyeing processes.  In the examples alkylene is methylene, ethylene, 2-methyl ethylene and tri- and tetra-methylene.