Patent GB-419366-A (GB)
Title: Production of dyeings and printings on fibrous material
IPC: D06P3/68
Filed: 1933-05-10
Abstract: Azo dyes are produced on the fibre by coupling an arylide of 2 : 3-oxynaphthoic acid with a diazotised arylether of an o-aminophenol containing one carboxylic ester group, which group is contained in the o-aminophenol residue.  Yellowish, scarlet-red to blue-red dyeings are obtained.  In an example the dyestuff ethylester of 4<1> - chloro - 2 - amino - 4 - carboxylic acid - 1 : 1<1> - diphenylether --> the a -naphthylamide is formed on cotton.  In a table the shades obtained by using the following additional components are given: the ethyl ester of 2-amino-4-carboxylic acid-1 : 1<1>-diphenylether and its 2<1>-chloro derivative; the 2<1>-methoxyanilide, the 2<1>-methyl-4<1>- or 5<1> chloranilide, the o - and p - anisidide, b - naphthalide, p-phenetidide, anilide and 2<1> : 5<1>-dimethoxyanilide of 2 : 3-oxynaphthoic acid.  The dyeings may also be produced on silk, regenerated cellulose or wool. Specifications 6379/12, [Class 2 (iii)], 17279/13, 195,600, 202,984, 294,883, 310,758, [all in Class 15 (ii)], and 383,064 (as open to inspection under Sect. 91 of the Acts), are referred to.  Arylethers of o-aminophenol carboxylic acid esters are made (1) by reducing the condensation products from esters of 2-nitro-1-chlorbenzene-4- or 5-carboxylic acid and phenol or its nuclear substitution products, e.g. o-, m- and p-cresol, o-, m-, and p-chlorphenol, chlorcresols, dichlorphenols, monoalkylethers of hydroquinone, resorcinol or pyrocatechol, chlor-guaiacol (1-oxy-3 - chloro - 6 - methoxybenzene) or naphthols, or 2) by condensation of the 2-nitro-1-chlorbenzene-4- or 5-carboxylic acid with the above phenols or naphthols, esterification and reduction.  The Specification as open to inspection under Sect. 91 comprises also the manufacture of azo dyes in substance or on the fibre by coupling an arylide of 2 : 3-oxynaphthoic acid with a diazotised aryl- or aralkyl-ether of an o-aminophenol which contains a carboxylic acid ester group.  In examples the following dyes are produced in substance or on the fibre: (1) ethyl ester of 2-amino-4-carboxylic acid-1 : 1<1>-diphenylether --> b -naphthalide; (2) methyl ester of 2-amino-4-chloro-1 : 1<1>-diphenylether-4<1>-carboxylic acid--->o-anisidide; (3) ethylester of 4 - chloro - 2 - amino - 4 - carboxylic acid - 1 : 1<1> - diphenylether ---> 2<1> - methoxy - 5 - methylanilide; (4) ethyl ester of 2-amino-4-chloro - 1 : 1<1> - diphenylether - 4<1> - carboxylic acid ---> p-toluidide; (5) ethyl ester of 2<1> : 5<1>-dichloro - 2 - amino - 4 - carboxylic acid - 1 : 1<1> - diphenylether ---> p-ethoxyanilide; (6) ethylester of 2 - amino - 4 - chloro - 1 : 1<1> - diphenylether 3<1> - carboxylic acid --->anilide; (7) methyl ester of 4<1> - chloro - 2 - amino - 1 : 1<1> - diphenylether - 5 - carboxylic acid ---> o - toluidide.  A table is given showing the shades obtainable on cotton or regenerated cellulose by use of the following additional components : 2 - methyl - 4 - methoxyanilide, o - m - or p - chloranilide, m - toluidide, 2 - methoxy - 4 - or 5 - chloranilide, 2 : 4 - or 2 : 5 - dimethylanilide, 2 - ethoxy - 5 - methylanilide, m-nitranilide, 2 : 4-dimethoxy - 5 - chloranilide, o - ethoxyanilide, 3 : 4 - dichloranilide, and 2 - ethyl - 5 - methyl anilide; the methyl or ethyl ester of 2<1>-, 3<1>-, or 4<1> - methyl - 2 - amino - 4 - carboxylic acid - 1 : 1<1>-diphenylether, the methyl ester of 2-amino-4-carboxylic acid-1 : 1<1>-diphenylether or its 4<1>-chloro derivative, the ethylester of 4<1>-chloro-2 - amino - 5 - carboxylic acid - 1 : 1<1> - diphenylether, the methyl or ethyl ester of 2-amino-4-chlor - 1 : 1<1> - diphenylether - 4<1> - carboxylic acid, the ethyl or methyl ester of 2-amino-1 : 1<1> - diphenylether - 3<1> - or 4<1> - carboxylic acid, and the diethyl ester of 2-amino-1 : 1<1> - diphenylether - 4 : 4<1> - dicarboxylic acid. Isopropyl-, n-butyl, benzyl, phenyl, tolyl and methoxy- or ethoxy-phenyl esters are also specified as diazo components. Carboxylic acid esters of aryl- or aralkylethers of o-aminophenols are made (1) by reducing the condensation products from alkyl-, aralkyl- or arylesters of 2-nitro-1-chlorobenzene-4- or 5-carboxylic acids and phenol or its derivatives such as o-, m- and p-cresol, o-, m- and p-chlorophenol, chlorcresols, dichlorophenols, brom-or iodophenols, monoalkylethers of hydroquinone, resorcinol or pyrocatechol, chloroguiacol, naphthols or benzylalcohol; (2) by condensation of 2-nitro-1-chlorobenzene-4- or 5-carboxylic acid with the above phenols, esterification and reduction; (3) by condensing an o-nitrophenolcarboxylic acid ester, such as 1-oxy-2-nitrobenzene-4-carboxylic acid-methyl-, ethyl-, propyl-, butyl-, amyl or phenyl-ester, with benzyl chloride and reducing; (4) by condensing 1 - halogen - 2 - nitrobenzenes or 1 - halogen - 2 - nitro - 4 - or 5 - halogen -benzenes with a phenolcarboxylic acid, such as o-, m- or p-oxybenzenecarboxylic acid or a derivative thereof, e.g. a cresolcarboxylic or a chlorphenolcarboxylic acid, esterifying and reducing or vice versa. This subject-matter does not appear in the Specification as accepted.