Patent GB-756843-A (GB)
Title: Manufacture of monoazo-dyestuffs insoluble in water
IPC: C09B29/20
Filed: 1952-08-11
Abstract: Water-insoluble monoazo dyestuffs of the general formula <FORM:0756843/IV(a)/1> (wherein one of X1 and X2 represents a halogen atom and the other an -OR group, R represents a methyl or ethyl group, Y a hydrogen or halogen atom or an alkoxy group, and Z an alkoxy group) may be used for colouring acetate or viscose rayon or cellulose ester or ether films by incorporating them in the spinning or casting solutions, or for colouring artificial resins, e.g. condensation products of formaldehyde with urea, phenols or amines. In an example, the dyestuff obtained by coupling diazotized 1-amino - 2 - methoxybenzene - 5 - carboxylic acid amide with 1-(21:31-hydroxynaphthoylamino) -2:4-dimethoxy-5-bromobenzene is ground in a ball mill with a urea-formaldehyde condensate and wood meal and the resulting mixture is moulded.  In another example, the dyestuff is used in conjunction with an emulsion of polyvinyl acetate and a hardenable urea-formaldehyde condensate for pigment printing of textiles.  Specifications 331,247, 332,932, [both in Class 2 (iii)], and 343,419; German Specification 613,234 and U.S.A. Specification 1,984,739 are referred to.ALSO:The invention comprises water-insoluble monoazo dyestuffs of the general formula <FORM:0756843/IV(c)/1> (wherein one of X1 and X2 represents a halogen atom and the other an -OR radical, R represents a methyl or ethyl group, Y a hydrogen or halogen atom or an alkoxy group, and Z an alkoxy group), and the preparation thereof by coupling the appropriate components in substance, on a substratum to produce a lake, or on the fibre (e.g. vegetable fibres, including regenerated cellulose) to produce a dyeing or print.  The dyestuffs produced in substance may be applied to textiles by padding or printing in the presence of binding agents, and may also be used for colouring acetate or viscose rayon or cellulose ester or ether films by incorporating them in the spinning or casting solutions, or for colouring natural or artificial resins (see Group IV(a)).  In examples: (1) cotton yarn is impregnated with a solution of 1-(21:31-hydroxynaphthoylamino) - 2:4 - dimethoxy -5-chlorobenzene in aqueous alcoholic caustic soda containing formaldehyde and Turkey red oil, and a bluish red dyeing is developed with a diazo solution from 1-amino -2 - methoxybenzene - 5 - carboxylic acid amide; (2) the coupling component in (1) is replaced by 1 - (21:31-hydroxynaphthoylamino) - 2:5 - dimethoxy - 4 - chlorobenzene, yielding a pink dyeing; (3) cotton or viscose fabric is printed with a paste containing the coupling component of (1) or (2), the diazoamino compound from diazotized 1 - amino - 2 - methoxybenzene - 5 - carboxylic acid amide, alcohol, aqueous caustic soda and starch-tragacanth thickening, and a pink print is developed by the action of steam mixed with acetic or formic acid vapour; (4) the dyestuff of (2) is prepared in substance and may be used to produce red prints on textiles, e.g. from an emulsion of polyvinyl acetate and a water-soluble, hardenable urea-formaldehyde condensate; (5) the dyestuff of (1) is produced in substance or on a carrier for the production of a lake; (6) the coupling component in (5) is replaced by 1-(21:31 - hydroxynaphthoylamino) - 2:4 - dimethoxy - 5 - bromobenzene.  A Table gives the properties of further dyestuffs, the following additional components being specified: diazo component: 1 - amino - 2 - ethoxybenzene - 5 - carboxylic acid amide; coupling components: 1 - (21:31 - hydroxynaphthoylamino) - 2:5 - dimethoxy - 4 - bromobenzene and - 2:5 - diethoxy - 4 - chlorobenzene, 1 - (61 - bromo - 21:31 - hydroxynaphthoylamino) - 2:5 - dimethoxy - 4 - chlorobenzene and - 2:4 - dimethoxy - 5 - chlorobenzene, and 1 - (61 - methoxy - 21:31 - hydroxynaphthoylamino) - 2:4 - dimethoxy - 5 - chlorobenzene.  Specifications 331,247, 332,932 [both in Class 2(iii)] and 343,419 [Group IV], U.S.A. Specification 1,984,739 and German Specification 613,234 are referred to