GB462233A - Manufacture of azo-dyestuffs - Google Patents

Abstract

Monoazo dyes insoluble in water are made by coupling a diazo compound free from sulphonamide groups and groups which impart to the azo dyes solubility in water, such as SO3H or COOH, with a monoacyl-m-phenylenediamine of the formula <FORM:0462233/IV/1> [Ac = an acyl residue of an aliphatic carboxylic acid, e.g. HCO--, CH3.CO,-- C2H5.CO--, C3H7.CO--, C11H23.CO--, OH.C2H4.CO--, NH2.CH2.CO-- or alkyl2.N.CH2.CO--, R1 = an aliphatic or aromatic radical such as methyl, ethyl, propyl, butyl, b -oxyethyl, b : g -dioxypropyl, b -oxy-g -chlorpropyl, b -oxy-g -alkoxypropyl, epoxypropyl or phenyl, R2 = H or a like radical to R1, R1 and R2 being the same or different in the case of tertiary substituted nitrogen] and which may contain other nuclear substituents. They dye cellulose esters and ethers in yellow, red, violet and blue to green blue tints and are also suitable for colouring cellulose ester and ether lacquers, fats and soaps. They are soluble in alcohols, ketones hydrocarbons, such as petroleum, paraffin oil benzine, benzene, oils and waxes. In the examples dyes from the following components are described: diazo components: 2 : 4-dinitroaniline, 5- or 6-chlor-2 : 4-dinitroaniline, 3- or 4-nitroaniline, 5-nitro-2-anisidine, 2-chlor-4-nitroaniline, 2 : 6-dichloro-4-nitroaniline and 2 : 4-dichloraniline; coupling components: 4-methoxy-3-(ethyl-b -g -dioxypropyl) aminoacetanilide (obtained by ethylating 4-methoxy-3-mono (b -g -dioxypropyl)-aminoacetanilide) or the corresponding formyl, propionyl or lactyl compounds, 4-methoxy-3-diethylamino lauric acid anilide (obtained by reducing 4-methoxy-3-nitroacetanilide, ethylating with diethyl sulphate, saponifying and treating with lauric acid chloride), 3-diethylaminolaurylanilide (by condensing N-diethyl-m-phenyleneldiamine with lauric acid chloride), 4-methoxy 3-diethylaminolactic acid anilide (obtained by heating 4-methoxy-3-diethylamino-1 - aniline with lactic acid ethyl ester in a closed vessel), 4-methoxy-3-(bisoxyethyl) - aminoacetanilide, or the corresponding lactyl, formyl or n-butyryl compounds (obtained by heating the corresponding 4-alkoxy-3-aminoacylanilide with ethylene chlorhydrin in presence of an acid binding agent the 4-alkoxy-3-aminoacylanilides being made, e.g. by acylating p-aminopheno methyl or ethyl ether with n-butyric, acetic, lactic or formic acid or an ester or chloride thereof, nitrating and reducing), 4-methoxy-3-mono-(b : g -dioxypropyl) - aminoacetanilide (obtained by heating 4-methoxy-3-aminoacetanilide with glycerine-a -chlorhydrin) or the corresponding formanilide, lactanilide or n-butyranilide or the corresponding 4-ethoxy compounds. Specifications 245,790, 251,155, 274,823, 292,180, and 422,843, [all in Class 15 (ii)], are referred to.ALSO:Fats, soaps, alcohols, ketones, hydrocarbons, such as petroleum, paraffin oil, benzene, benzine, oils and waxes are coloured by means of monoazo dyes made by coupling a diazo compound free from sulphonamide groups and groups which impart to the dyes solubility in water, such as SO3H or COOH, with a monoacyl-m-phenylenediamine of the formula <FORM:0462233/III/1> [Ac = an acyl residue of an aliphatic carboxylic acid, e.g. H.CO, CH3CO, C2H5CO, C3H7CO, C11H23CO, OHC2H4CO, NH2CH2CO o alkyl2N.CH2CO; R1 = an aliphatic or aromatic radical such as methyl, ethyl, propyl, butyl, b -oxyethyl, b :g -dioxypropyl, b -oxy-g -chlorpropyl, b -oxy-g -alkoxypropyl, epoxypropyl or phenyl; R2 = H or a like radical to R1, R1 and R2 being the same or different in the case of tertiary substituted nitrogen] and which may contain other nuclear substituents.