GB819664A - Improvements in or relating to water-insoluble monoazo dyestuffs - Google Patents

Abstract

The invention comprises dyestuffs of formula <FORM:0819664/IV (c)/1> where the two R's are identical or different alkyl radicals of 1-4 carbon atoms which together have at least one negative substituent selected from halogen atoms and the nitro, nitrile and C-acyl groups and at least one -O-acyl radicle of 1-5 carbon atoms in a different R from the one containing the negative substituent, R1 is the residue of a mono- or bi-nuclear diazo component free from SO3H or COOH groups, preferably of the benzene naphthalene or heterocyclic series containing a sulphur atom in o-position to the diazo group and A may have further substituents other than SO3H or COOH groups. A particularly preferred group of dyestuffs have the formula <FORM:0819664/IV (c)/2> where v is H or F, w is F or CN, X is MeSO2 or NO2, y is H, Cl, Br, CN, CF3, MeSO2 or SO2 and z is H or Me. They may be made by coupling, preferably in an acid medium, an appropriate mono- or di-nuclear compound with the required tertiary amine or by esterifying corresponding dyestuffs containing N-hydroxy-alkyl groups. The acyl groups are -CO-alkyl groups. Specified or indicated diazo components are 4-nitro and -alkylsulphonyl-anilines and their 2- or 2,6-substituted derivatives, 4 - alkylsulphonyl - 1 - naphthylamine and 1 - naphthylamine - 4 - sulphonic acid fluoride and their derivatives and 2-amino-thiazole, -thiophene and -thiodiazole and their derivatives. The tertiary amines, when substituted, preferably contain halogen atoms or alkyl, alkoxy or acylamino groups, whose H atoms may be replaced by F atoms, in the 2-and/or 5- position of nucleus A. The dyestuff dye cellulose ester, polyamide, polyvinyl, terephthalic acid ester and polyacrylonitrile fibres by a dispersion process in orange, red and violet shades and they may also be used for colouring lacquer, oils and synthetic resins. In examples, which illustrate the preparation of the dyestuffs and their use in dyeing processes: (1) 2-bromo-4 - nitro - 41 - (N - b - cyanoethyl - N - b - hy - droxyethylamino) - 1,11 - azobenzene and (2) 1 - methylsulphonyl - 4 - [21 - methyl - 41 - (N-b -cyaroethyl - N - b - hydroxyethylamino)] - phenyl-azonaphthalene are acetylated and (3) the dyestuff 1 - methyl - sulphonyl - 4 - naph - thylamine -->1 - (N - b - cyanoethyl - N - b - acetoxyethylamino) - 3 - toluene is made. In the examples, various alternative reactants are specified and a table of dyestuffs obtainable as in the examples is also provided, the components used being selected from those indicated above with the addition of 2-amino-benzothiazoles. Reference has been directed by the Comptroller to Specifications 723,933 and 744,877.