Patent GB-211223-A (GB)
Title: Manufacture of new azo-dyestuffs
IPC: C09B29/15
Filed: 1922-11-15
Abstract: Azo dyes are prepared by coupling diazo compounds with derivatives of 1-naphthol of the general formula <FORM:0211223/2/1> wherein B represents an aryl group or an NH-aryl group.  Such derivatives are the 4 : 41-dioxy-dinaphthyl-ketone and its 3 : 31-dicarboxylic acid described in Specifications 181,000 and 195,513, the 4-oxynaphthalene-1-arylketones and their carboxylic acids described in Specification 203,824, and the arylamides of 1-naphthol-4-carboxylic acid.  Acid dyestuffs for wool, or dyestuffs for pigments or lakes may be produced according to the nature of the diazo compound used; with unsulphonated diazo compounds fast shades may be produced by forming the dyestuffs on the fibre; red, orange-red, violet-red, &c. shades are thus obtained.  The following examples are given: (1) diazotized 2-anisidine-4-sulphonic acid is coupled with 4 : 41-dioxydinaphthylketone-3 : 31-dicarboxylic acid; (2) diazotized metanilic acid is coupled with 4-oxynaphthalene-1-phenylketone or its 3-carboxylic acid; the product gives red barium lakes; 2-naphthylamine-1-or 6-sulphonic acid and the ketone also give blood-red lake dyestuffs; (3) diazotized 4-chlor-2-aminodiphenylether is coupled with 4-oxynaphthalene-1-(21-chloro)-phenylketone or its 3-carboxylic acid; (4) red shades are produced on cotton by impregnating with 4 : 41-dioxydinaphthyl-ketone, or the anilide of 1-naphthol-4-carboxylic acid, or 4-oxynaphthalene-1-phenylketone, and passing through a bath of diazotized o-toluidine, o-aminoazotoluene, or 1-chlor-2-naphthylamine, or by printing with a paste containing diazotized 5-nitro-2-anisidine.  A table is also given showing the shades obtainable from the following combinations:-4 : 41-dioxydinaphthylketone or its 3 : 31-dicarboxylic acid and o-toluidine, 2 anisidine-4-sulphonic acid, o-and p-toluidine sulphonic acids (CH3 : NH2 : SO3H=1 : 2 : 4 or 1 : 4 : 3), or dianisidine: 4-oxynaphthalene-1-phenylketone or its 3-carboxylic acid and metanilic or sulphanilic acid, naphthylamine sulphonic acids 1 : 4, 2 : 1, 2 : 6, p-nitraniline, 4-chlor-2-anisidine, 4-nitro-2-toluidine, 5-nitro-2-anisidine, p-chloraniline, 2 : 5-dichloraniline, a -naphthylamine, 1-chlor-2-naphthylamine, 4-chlor-2-amino phenol-phenylether, -4-chlorphenylether, -benzylether, -p-cresylether, or -4-chlor-3-cresylether, 2-aminophenol-phenylether, 3-amino-1-methyl-4-phenol-benzylether, 4-ethylsulphon-2-aminophenol-phenylether, benzidine, dianisidine, 4 : 41-diaminodiphenylamine, 4 : 41-diaminodiphenylether, or o-aminoazotoluene : 4-oxynaphthalene-1-(21-chloro)-phenylketone or its 3-carboxylic acid and 1-chlor-2-naphthylamine, 4-ethylsulphon-2-aminophenol-benzylether, or dianisidine: 1-chloro-41-oxy-2 : 11-dinaphthylketone or its 31-carboxylic acid and 4-chlor-2-aminophenolphenyl- or benzyl-ether, or dianisidine; 1-oxynaphthalene-4-carboxylic anilide, p-toluidide, or methylanilide, and 4-chlor-2-aminophenol-phenylether.  Arylamides of 1 -oxynaphthalene-4-carboxylic acid are obtained by action of aromatic amines on one of the esters of 1-oxynaphthalene-4-carboxylic acid described in Specification 181,009.  4-Chlor-3-cresylether of 4-chlor-2-aminophenol is prepared by condensing chlorcresol (OH : Cl : CH3 = 1 : 4 : 3) with 1 : 4-dichlor-2-nitrobenzene and reducing. 4-Ethylsulphon-2-aminophenol-phenyl- or benzyl-ether is obtained by reducing the corresponding nitro compound which can be made by converting 1-chlor-2-nitrobenzene-4-sulphonic chloride into the sulphonic acid, ethylating the product and exchanging Cl for O.C6H5 or O.CH2-C6H5.ALSO:Textile fibres are dyed in fast red to blue shades by impregnating with derivatives of 1-naphthol of the general formula <FORM:0211223/15/1> wherein R represents an aryl group or an NH-aryl-group, and developing or printing with a non-sulphonated diazo compound. Such derivatives are the 4 : 41-dioxy-dinaphthylketone and its 3 : 31-dicarboxylic acid described in Specifications 181,009 and 195,513, the 4-oxynaphthalene-1-arylketones and carboxylic acids described in Specification 203,824, and the arylamides of 1-naphthol-4-carboxylic acid.  Examples are given in which red shades are produced on cotton by impregnating with 4 : 41-dioxydinaphthylketone, or the anilide of 1-naphthol-4-carboxylic acid, or 4-oxynaphthalene-1-phenylketone, and passing through a bath of diazotized o-toluidine, o-aminoazotoluene, or 1-chlor-2-naphthylamine, or by printing with a paste containing diazotized 5-nitro-2-anisidine.  A table is also given showing the shades obtainable from the following pairs of components :-4 : 41-dioxydinaphthylketone or its 3 , 31-dicarboxylic acid and o-toluidine, 2-anisidine-4-sulphonic acid, o- or p-toluidine sulphonic acids (CH3 : NH2 : SO3H=1 : 2 : 4 or 1 : 4 : 3) or dianisidine; 4oxynaphthalene-1-phenyl-ketone or its 3-carboxylic acid and metanilic acid, sulphanilic acid, naphthylamine sulphonic acids 1 : 4, 2 : 1, 2 :6, p-nitraniline, 4-chlor-2-anisidine, 4-nitro-2-toluidine, 5-nitro-2-anisidine, p-chloraniline, 2 : 5-dichloraniline, a -naphthylamine, 1-chlor-2-naphthylamine, 4-chlor-2-aminophenol-phenylether, 4-chlorphenylether, -benzylether, -p-cresylether, or 4-chlor-3-cresylether, 2-aminophenol-phenylether, 3-amino-1-methyl-4-phenol-benzylether, 4-ethyl-sulphon-2-aminophenol-phenylether, benzidine, dianisidine, 4 : 41-diamino-diphenylamine, 4 : 41 diamino - diphenylether, or o - aminoazotoluene: 4 - oxynaphthalene - 1 - (21 - chloro) - phenylketone or its 3-carboxylic acid and 1-chlor-2-naphthylamine, 4-ethylsulphon-2-aminophenolbenzylether, or dianisidine : 1-chlor-41-oxy-2 : 11-dinaphthylketone or its 31-carboxylic acid and 4-chlor-2-aminophenol-phenyl-or-benzyl-ether, or dianisidine; 1-oxynaphthalene-4-carboxylic anilide, p-toluidide, or methylanilide, and 4-chlor-2-aminophenol-phenylether.