Patent GB-835470-A (GB)
Title: Improvements in or relating to heterocyclic monoazo dyestuffs and their chromium andcobalt complex compounds
IPC: C09B45/14
Filed: 1957-07-09
Abstract: 2 - Amino - 1 - hydroxy - 4 - chloro - 6 - X - benzene where X is a group of formula <FORM:0835470/IV (b)/1> is made by treating 4-chloro-6-aminophenol with chloroformic acid-21-chloroethyl ester to yield 4 - chloro - 6 - carbo - 21 - chloro - ethoxyaminophenol, effecting nitrogen ring closure by treatment with warm caustic soda, and nitrating and subsequently reducing the product thus obtained. The products are dyestuff intermediates.  Specification 753,987 is referred to.ALSO:The invention comprises dyestuffs of formula <FORM:0835470/IV(c)/1> where B is the residue of an azo component coupling ortho to Z which is a phenolic or enolic OH group or a primary or secondary amino group, y is a metal-complex forming substituent, n is 1 or 2, and m 2 or 3 and A and B may contain further substituents the heterocyclic grouping being either in A or B, or both A and B. The invention also includes their chromium and cobalt complexes, the 1,2-complexes being preferred.  The metal-free dyestuffs are made by coupling an appropriate diazotized aniline with the required coupling component and, if desired, metallizing in substance or on the fibre.  The diazotization, coupling and metallization are effected in conventional fashion.  Coupling with hydroxy or enolic compounds is effected preferably in weakly acid to strongly alkaline media and with amines in a weakly acid, preferably acetic acid, medium.  Preferred values for y are OH, MeO and COOH. Indicated as substituents for A are halogen atoms and nitro, acetyl-, benzoyl-, carbomethoxy- and carboethoxy-amino-, carboxy, methyl, ethyl, tert. butyl, methoxy, sulpho, sulphonamide, sulphomethyl-, -dimethyl-, -(21-hydroxyethyl)-di(21-hydroxyethyl)-, -(31-hydroxy- and -methoxy-propyl)-, -phenyl- and -(21-carboxy)-phenyl-amido and methylsulphonyl groups and the above heterocyclic groups.  Indicated as azo components are phenols, naphthols, naphthylamines, alkyl-, cycloalkyl-, aralkyl- and arylaminonaphthalenes, 1 - aryl - 3 - methyl - 5 - pyrazolones and acylacetylamino - alkanes, -benzenes and -naphthalenes which may carry the same substituents as the diazo components, the heterocyclic substituents being preferred.  The dyestuffs dye wool, silk, leather and polyamide fibres by the after-chroming and onebath chroming processes in red, yellow, green, blue, violet, grey and brown shades.  The metal dyes dye the same materials from neutral to weakly acid dye-baths in similar shades. Those of the dyestuffs that have a high solubility in organic solvents may be used for dyeing man-made fibres and plastics and lacquer media.  In examples which illustrate the preparation of the dyestuffs and their use in dyeing processes the diazo components used are 2 - amino - 4 - chloro - 6 - X - (where X is the heterocyclic component with m=2)-phenol, 2 - amino - 4 - nitrophenol and 2 - aminophenol-4-sulphonamide and -sulphonmethylamide and the coupling components are 1-acetylamino-7-naphthol, 2-Y-(where Y is the heterocyclic component with m=3)-4-methylphenol, 2-(31-X - phenylamino) - naphthalene and 1 - Y - 7-naphthol.  A table is also provided of a great number of dyestuffs obtained by the above processes and the results of their use in dyeing wool or spun-dyed fibres the components used being selected from those indicated above with cyano and various N-substituted sulphonamide groups as additional substituents.  Specification 753,987 is referred to.