Patent GB-541968-A (GB)
Title: Manufacture of polyazo-dyestuffs
IPC: C09B31/00
Filed: 1940-06-10
Abstract: 541,968. Azo dyes. SOC. OF CHEMICAL INDUSTRY IN BASLE. June 10, 1940, Nos. 10087 and 10088. Convention dates, June 10, 1939 and May 7, 1940. [Classes 2 (iii) and 15 (ii)] Polyazo dyes are obtained by coupling a diazotized initial component with a middle component, further diazotizing and coupling with an end component or with a further middle component, followed by further diazotization and coupling with an end component, the initial component being an aminosalicylic acid or a substitution product thereof, the middle component or a middle component being a compound of the general formula wherein R represents a residue of the benzene series, Y represents an alkyl, O-alkyl or O- aralkyl group, Z represents the residue of a fatty acid having not more than 7 carbon atoms which is linked with the O atom by a carbon atom of its chain, the substituents Y and OZ being in p-position to one another and the amino group being in o-position to the substituent OZ, and the end component (coupled alkaline) being a naphtholsulphonic acid linked by an -NH- group to a 1:3:5- triazine residue carrying, as a substituent, at least once, the residue of a p-aminoazo dyestuff. Specified initial components are 5- amino-2-hydroxybenzoic acid and its alkyl and halogen substitution products, specified groups Y are methyl, methoxy, ethoxy and benzyloxy, specified groups OZ are the residues of hydroxyacetic and hydroxypropionic acids, specified other middle components are cresidine and 1 : 6- and 1 : 7 -aminonaphthalenesulphonic acids. The 1:3:5-triazine derivative end components may be obtained as described in Specification 221,843, [Class 2 (iii)], specified aminonaphtholsulphonic acids being 1 : 8 : 4-aminonaphtholsulphonic and 1:8:3:6-, 1:8:4:6- and 1 : 8 : 2 : 4-aminonaphtholdisulphonic acids and specified p-aminoazo dyestuffs being 4 - amino - 4<SP>1</SP> - hydroxy - azobenzene - 3<SP>1</SP> - carboxylic acid and its 51-methyl and 51-chloro derivatives. The products dye cellulosic fibres, e.g. of cotton, linen, or regenerated cellulose, and the fastness of the dyeings may be improved by after-treatment, e.g. as described in Specification 455,274 or 468,362, with an agent yielding metal, especially copper. The metal, e.g. copper or chromium, compounds may also be produced in substance. Examples (1) and (2) relate to the production of the dyestuffs, (1) (a) 5-amino-2-hydroxybenzoic acid# 4-methoxy-2-amino-phenoxyacetic acid# (alkaline) the condensation product from cyanuric chloride (1 mol.), 1: 8 : 3 ; 6-aminonaphtholdisulphonic acid (1 mol.), 4-amino-4<SP>1</SP>- hydroxy - azobenzene - 3<SP>1</SP> - carboxylic acid (1 mol.) and aniline (1 mol.), (b) 5-amino-2- hydroxybenzoic acid# cresidine or 1 : 6- or 1 : 7 - aminonaphthalenesulphonic acid # 4 - benzyloxy - 2 - amino - phenoxyacetic acid# (alkaline) the same condensation product or the corresponding products in which the 1:8:3:6- acid is replaced by the 1 : 8 : 4 : 6- or the 1 : 8 : 2 : 4- acid or in which the 1:8:3:6- acid is replaced by the 1:8:4- acid and the aniline by ammonia ; (2) (a) 5-amino-2- hydroxybenzoic acid# 4-ethoxy-2-amino-phenoxyacetic acid# (alkaline) the condensation product of (1) (a) above, (b) the same in which the initial component is replaced by 3-methyl- or 3 - chloro - 5 - amino - 2 - hydroxybenzoic acid or the middle component by 4-methyl-2- amino-phenoxyacetic acid or the end component by the corresponding condensation product in which the 4-amino-4'-hydroxy-azobenzene is replaced by its 51-methyl or 5<SP>1</SP>- chloro derivative. An example is given of the dyeing of cotton with after-coppering of the dyeing. Specification 209,723, [Class 2 (iii)], also is referred to. Aminophenoxy derivatives of lower fatty acids, of the above general formula, in which Y is O-alkyl or O-aralkyl are obtained by treatment of the corresponding nitrohydroquinone alkyl or aralkyl ethers with aluminium chloride or a like catalyst of the Friedel-Craft type to hydrolyze the ether group in o-position to the nitro group, thereupon reducing the nitro group, treating the product with chloracetyl chloride or other chlorinated lower fatty acid chloride and converting the resulting morpholone or like ring compound into the corresponding phenoxy lower fatty acid derivative.