Patent GB-777200-A (GB)
Title: Direct-dyeing trisazo-dyestuffs of the diphenyl series and process for their manufacture
IPC: C09B35/366
Filed: 1955-10-25
Abstract: The invention comprises dyestuffs of formula <FORM:0777200/IV(b)/1> where R1 is a 4,41- diphenyl residue containing 3,31- substituents which with the OH groups present in the adjacent residues in position vicinal to the azo groups are capable of forming metal complexes, R2 is a residue of a coupling component bound to the azo group through a ketomethylene group R3 is a residue of the benzene series which contains a sulphonic acid group and of which the carbon atoms bound to the NH group and the -N=N-group are separated from one another by at least two carbon atoms, and R4 is a residue of an 8 - oxyquinoline.  They are made by coupling an 8 - oxyquinoline, advantageously in an alkaline medium with the addition of an organic base such as pyridine or picoline, with a diazo-compound of an appropriate amino-disazo dyestuff which has preferably been diazotized by the indirect method.  The amino-disazo dyestuff is made by coupling tetrazotized diphenyl compounds with appropriate keto-methylene and J-acid components, optionally in the presence of alcohol or pyridine.  Preferably the 3,31- diphenyl substituents are capable of forming stable metal complexes directly with the necessary hydroxy groups e.g. carboxymethoxy, carboxy and hydroxy, substituents the latter being preferred. Specified keto-methylene components are listed from acylacetylaminoaryl compounds and pyrazolones.  The phenyl radicles of the pyrazolones may contain halogens e.g. chlorine and bromine, atoms, alkyl and alkoxy groups such as methyl, ethyl, methoxy and ethoxy groups and particularly groups imparting solubility in water such as sulphonamide and sulphonic and carboxylic acid groups.  Pyrazolones mentioned are 1 - phenyl -, 3 - methyl- and 1 - phenyl-, and (21-, 31-, and 41- chloro - and methyl - phenyl) - 3 - methyl - 5 - pyrazolones, 1 - phenyl - 5 - pyrazolone - 3 - carboxylic acid, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 31 - and - 41 - sulphonic or carboxylic acid and - 31 - sulphonamide, 1 - (41 - oxyphenyl) - 3 - methyl - 5 - pyrazolone - 31 - carboxylic acid and aceto - and benzoyl - acetylamino - benzene.  J-acid derivatives mentioned as coupling components are 2 - [411 - amino - 11, 111 - diphenylamino(41)] - 5 - naphthol - 7.311 - disulphonic acid and 2 - (41 - aminophenylamino) - 5 - naphthol - 7,31 - disulphonic acid.  8 - Oxyquinoline and its 7 - sulphonic acid are specified end components.  Desirably the products contain 2 - 3 sulphonic acid groups per mol.  The dyestuffs dye animal and especially cellulosic fibres e.g. wool, silk, leather, cotton, linen, artificial silk and regenerated cellulose.  The dyeings may be metallized on the fibre or in the dyebath advantageously with copper-yielding agents, those dyestuffs being especially suitable which have no sulphonic acid groups other than those indicated in the above formula.  The one bath metallization of Specification 455,274 [Group IV] may be adapted. The dyeings may be after-treated with a basic condensation product of formaldehyde as in Specification 619,969. In examples which illustrate the preparation of the dyestuffs and their use in dyeing cotton in navy blue tints by an after-coppering process an additional diphenyl component used to certain of those specified above is 3,31 - dimethoxy - 4,41-diamino - diphenyl.