Disazo dyestuffs containing a thiazole central component

The invention relates to disazo-thiazole dyestuffs which in the form of the free acid correspond to the formula ##STR2## wherein D represents the radical of an aromatic carbocyclic or heterocyclic diazo component,
K represents the radical of a carbocyclic or heterocyclic coupling component,
A and B represent a direct bond or a bridge member,
R.sub.1 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, optionally substituted phenyl or naphthyl, carbo-C.sub.1 -C.sub.4 -alkoxy, cyano or optionally substituted carboxamide,
R.sub.2 represents C.sub.1 -C.sub.4 -alkyl or optionally substituted phenyl or naphthyl and
m and n represents 0, 1 or 2, and the sum of m and n denotes 1 or 2.
Suitable aromatic-carbocyclic diazo components D are those of the benzene and naphthalene series which can be substituted by halogen, cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, hydroxyl, thiocyanato, C.sub.1 -C.sub.4 -alkylsulphonyl, phenyl, phenylsulphonyl, benzylsulphonyl, 2-phenylethylsulphonyl, phenoxy or optionally substituted carboxamide or sulphonamide.
Suitable heterocyclic diazo components are those of the thiazole, benzthiazole, thiadiazole, triazole, pyrazole or thiophene series, which can optionally be substituted by C.sub.1 -C.sub.4 -alkyl, phenyl, halogen, cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, nitro or optionally substituted carboxamide.
Suitable carbocyclic and heterocyclic coupling components KH are those of the formulae given below ##STR3## wherein R.sub.3 and R.sub.4 represent hydrogen, optionally substituted alkyl or optionally substituted aralkyl,
R.sub.5 represents hydrogen, C.sub.1 -C.sub.4 -alkyl C.sub.1 -C.sub.4 -alkoxy, halogen, C.sub.1 -C.sub.4 -alkylsulphonyl, benzylsulphonyl, phenethylsulphonyl, optionally substituted phenylsulphonyl, optionally substituted sulphonamide or carboxamide, carbo-C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino, optionally substituted benzoylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino or optionally substituted phenylsulphonylamino,
R.sub.6 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonylamino, optionally substituted benzoylamino, C.sub.1 -C.sub.4 -alkylsulphonylamino or optionally substituted phenylsulphonylamino,
R.sub.7 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or cyano,
R.sub.8 represents hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,
R.sub.9 represents hydrogen or C.sub.1 -C.sub.4 -alkyl which is optionally substituted by hydroxyl, cyano, carboxyl or carboxamide,
R.sub.10 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, cyano, carbo-C.sub.1 -C.sub.4 -alkoxy, carboxamide or phenyl,
R.sub.11 represents hydrogen, C.sub.1 -C.sub.4 -alkyl or optionally substituted phenyl or naphthyl,
R.sub.12 represents hydrogen or C.sub.1 -C.sub.4 -alkyl,
R.sub.13 represents hydroxyl or NHR.sub.3,
R.sub.14 represents cyano, optionally substituted carboxamide or carbo-C.sub.1 -C.sub.4 -alkoxy,
R.sub.15 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, hydroxyl, carbo-C.sub.1 -C.sub.4 -alkoxy, phenyl or NR.sub.3 R.sub.4 and
X represents O or NH.
The sulphonic acid groups and sulphonylaminosulphonyl groups can be bonded via A and B, respectively, to the coupling component K, to the diazo component D or to the optionally substituted aryl radicals R.sub.1.
Suitable bridge members A and B are O, O-alkylene, O-alkylene-O, alkylene, alkylene-SO.sub.2 N-(R.sub.16)-alkylene-O-, SO.sub.2 -N-(R.sub.16)-alkylene, SO.sub.2 -N-(R.sub.16)-arylene, SO.sub.2 -N-(R.sub.16)-arylene-CH.sub.2 and SO.sub.2 -N-(R.sub.16)-alkylene-O,
wherein
R.sub.16 denotes hydrogen or C.sub.1 -C.sub.4 -alkyl.
Examples of possible substituents of the phenyl and naphthyl radicals R.sub.1, R.sub.2 and R.sub.11 and of the phenylsulphonyl, phenylsulphonylamino and benzoylamino radicals R.sub.5 and R.sub.6 are C.sub.1 -C.sub.4 -alkyl, nitro, halogen, C.sub.1 -C.sub.4 -alkoxy or phenyl.
Suitable substituents of the carboxamide and sulphonamide groups R.sub.1, R.sub.5 and R.sub.14, and on D are C.sub.1 -C.sub.4 -alkyl, phenyl, benzyl or phenethyl, and the sulphonamide groups can be mono-substituted or disubstituted. The alkyl substituents can also, with inclusion of the nitrogen atom, form a piperidine, pyrrolidine or morpholine ring.
As halogen for R.sub.5 and R.sub.7, as a substituent on D or on the abovementioned phenyl and naphthyl radicals, chlorine and bromine should be mentioned particularly.
Possible substituents of the alkyl radicals R.sub.3 and R.sub.4 are especially chlorine, bromine, cyano, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, benzyloxy, phenoxy, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenoxycarbonyloxy, phenylcarbonyloxy, C.sub.1 -C.sub.4 -alkylsulphonyl, benzylsulphonyl or phenylsulphonyl, the alkyl radicals preferably being unsubstituted or monosubstituted. The alkyl substituents can also, with inclusion of the nitrogen atom, form a piperidine, pyrrolidine or morpholine ring.
By optionally substituted aralkyl radicals there are in particular understood benzyl or phenethyl groups substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine, bromine or cyano.
Suitable alkylene groups in the bridge members are especially those with 2 to 4 C atoms, which can be straight-chain or branched. By arylene radicals in the bridge members there are preferably understood 1,2-, 1,3- or 1,4-phenylene radicals, and the phenylene radicals can be substituted further by C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl, benzyloxy, chlorine, bromine, cyano or nitro.
Preferred dyestuffs correspond to the formula ##STR4## wherein R.sub.1 ' denotes hydrogen, methyl, ethyl, or phenyl which is optionally substituted by chlorine, methyl, methoxy, ethoxy or nitro,
R.sub.17 and R.sub.18 denote hydrogen, chlorine, bromine, cyano,
C.sub.1 -c.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, carboxamide or sulphonamide which are optionally monosubstituted or disubstituted by C.sub.1 -C.sub.4 -alkyl, .beta.-hydroxyethyl, benzyl, phenyl or phenethyl, trifluoromethyl, phenoxy, C.sub.1 -C.sub.4 -alkylsulphonyl, phenylsulphonyl or benzylsulphonyl,
R.sub.19 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, chlorine or bromine,
K' denotes the radical of one of the coupling components listed below ##STR5## wherein R.sub.3 ' and R.sub.4 ' denote C.sub.1 -C.sub.4 -alkyl which is optionally substituted by C.sub.1 -C.sub.4 -alkoxy, phenoxy, hydroxyl, cyano, chlorine, methylcarbonyloxy, ethylcarbonyloxy, methoxycarbonyloxy or ethoxycarbonyloxy, or denote benzyl or 2-phenylethyl,
R.sub.5 ' denotes hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or C.sub.1 -C.sub.3 -alkylcarbonylamino,
R.sub.6 ' denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, chlorine or bromine, and
R.sub.20 and R.sub.21 denote hydrogen, C.sub.1 -C.sub.4 -alkyl, chlorine or bromine,
R.sub.8, r.sub.9 and X have the abovementioned meaning,
and the sulpho group is bonded to a phenyl radical R.sub.1 ', to the naphthalene or indole system, to the phenyl substituent of the iminopyrazoline or pyrazolone ring or to a hydroxyalkyl group, alkyl group, benzyl group or 2-phenylethyl group, R.sub.3 ' or R.sub.4 '.
A particularly preferred group of these dyestuffs are those which in the form of the free acid correspond to the formula ##STR6## wherein R.sub.17, R.sub.18 and R.sub.19 have the abovementioned meaning,
R.sub.3 " and R.sub.4 " denote C.sub.1 -C.sub.4 -alkyl which is optionally substituted by hydroxyl, cyano, acetoxy, methoxycarbonyloxy or chlorine, or denote benzyl or phenethyl and
R.sub.5 " denotes hydrogen, methyl, methoxy or acetylamino, and those which in the form of the free acid correspond to the formula ##STR7## wherein R.sub.17, R.sub.18, R.sub.19 and R.sub.1 ' have the abovementioned meaning, and
K" represents the radicals ##STR8## wherein R.sub.3 ", R.sub.4 " and R.sub.5 " have the abovementioned meaning and
R.sub.4 "' represents a benzyl radical substituted by sulpho or a C.sub.1 -C.sub.4 -alkyl radical which is substituted by sulpho or sulphato and is optionally substituted further by methoxy, phenyl or phenoxy.
Further preferred dyestuffs are those which in the form of the free acid correspond to the formula ##STR9## wherein R.sub.1 ', R.sub.18, R.sub.19 and K' have the abovementioned meaning,
E represents C.sub.1 -C.sub.4 -alkylene, O-C.sub.2 -C.sub.4 -alkylene-O or C.sub.2 -C.sub.4 -alkylene-O, the alkylene radicals optionally being substituted by C.sub.1 -C.sub.4 -alkoxy, phenoxy or phenyl,
p represents 0 or 1 and
Z represents OH, NH-SO.sub.2 -R.sub.2 ', N-(R.sub.16)-C.sub.2 -C.sub.4 -alkylene-SO.sub.3 H or N-(R.sub.16)-phenylene-SO.sub.3 H, R.sub.16 having the above-mentioned meaning, and
R.sub.2 ' represents C.sub.1 -C.sub.4 -alkyl or phenyl which is optionally substituted by methyl or chlorine.
Particularly preferred dyestuffs are those which in the form of the free acid correspond to the formula ##STR10## wherein R.sub.3 ", R.sub.4 ", R.sub.5 ", R.sub.18 and R.sub.19 have the abovementioned meaning and
Z' denotes OH, CH.sub.3 -SO.sub.2 -NH, phenyl-SO.sub.2 -NH, tolyl-SO.sub.2 NH or chlorophenyl-SO.sub.2 -NH and
R.sub.1 " represents H, CH.sub.3 or phenyl.
Further preferred dyestuffs are those which in the form of the free acid correspond to the formula ##STR11## wherein R.sub.1 ", R.sub.3 ", R.sub.4 " and R.sub.5 " have the abovementioned meaning.
The dyestuffs of the formula (I) are obtained by diazotising a diazo component of the formula
D - NH.sub.2
wherein
D represents the radical of an aromatic carbocyclic or heterocyclic diazo component,
and coupling the product with a thiazole of the formula ##STR12## wherein R.sub.1 has the abovementioned meaning,
again diazotising the amino-monoazo dyestuff and coupling the product with a coupling component of the formula
K - H
wherein
K represents the radical of a carbocyclic or heterocyclic coupling component,
and so choosing the components that they contain m groups (A-SO.sub.3 H) and n groups (B-SO.sub.2 NH-SO.sub.2 R.sub.2),
wherein
A, b, r.sub.2, m and n have the abovementioned meanings.
Examples of amines suitable for use as diazo components are: 2-aminonaphthalene-1-sulphonic acid, 4-aminonaphthalene-1-sulphonic acid, 5-aminonaphthalene-1-sulphonic acid, 6-aminonaphthalene-1-sulphonic acid, 7-aminonaphthalene-1-sulphonic acid, 8-aminonaphthalene-1-sulphonic acid, 1-aminonaphthalene-2-sulphonic acid, 4-aminonaphthalene-2-sulphonic acid, 5-aminonaphthalene-2-sulphonic acid, 6-aminonaphthalene-2-sulphonic acid, 7-aminonaphthalene-2-sulphonic acid, 8-aminonaphthalene-2-sulphonic acid, 2-aminobenzenesulphonic acid, 4-chloro-2-aminobenzenesulphonic acid, aniline, 2-, 3- and 4-chloroaniline, 2,5-dichloroaniline, 2,4-dichloroaniline, 3-bromoaniline, 2-bromoaniline, 2-trifluoromethylaniline, 2-, 3- and 4-toluidine, 2-, 3- and 4-anisidine, 2-ethylaniline, 4-propoxyaniline, 4-benzylsulphonylaniline, 2-chloro-4-ethylsulphonylaniline, 2,5-dichloro-4-propylsulphonylaniline, aniline-4-N,N-dimethylsulphonamide, 2-chloroaniline-4-sulphonamide, 2-trifluoromethylaniline-4-N-benzylsulphonamide, 2,5-dichloroaniline-4-sulphonanilide, 2-chloroaniline-4-(2-methyl)-sulphonanilide, 2,5-dichloroaniline-4-N-hydroxypropylsulphonamide, 2-chloroaniline-4-N-cyclohexylsulphonamide-2-trifluoromethylaniline-4-N-methyl-N-phenylsulphonamide, 2-chloro-5-bromoaniline-4-N,N-dimethylsulphonamide, 2-chloro-6-methylaniline-4-N-methylsulphonamide, 2,5-dibromoaniline-4-N-benzylsulphonamide, aniline-4-sulphonic acid, 2-chloroaniline-4-sulphonic acid, 2,5-dichloroaniline-4-sulphonic acid, 2,5-dibromoaniline-4-sulphonic acid, 2-trifluoromethylaniline-5-sulphonic acid, 2-bromoaniline-4-sulphonic acid, 2,6-dibromoaniline-4-sulphonic acid, 2,6-dicyanoaniline-4-sulphonic acid, 2-trifluoromethyl-5-chloroaniline-4-sulphonic acid, 2-methylaniline-4-sulphonic acid, 3-methylaniline-4-sulphonic acid, 3-chloroaniline-5-sulphonic acid, 2,5-dimethoxyaniline-4-sulphonic acid, 1-aminonaphthalene-4-sulphonic acid, (3-amino-4-chlorobenzenesulphonyl)-methanesulphonamide, (3-amino-4-chlorobenzenesulphonyl)-butanesulphonamide, (3-amino-4-chlorobenzenesulphonyl)-o-toluenesulphonamide, (3-amino-4-chlorobenzenesulphonyl)-benzenesulphonamide, (3-amino-6-methylbenzenesulphonyl)-benzenesulphonamide, (3-amino-6-methoxybenzenesulphonyl)-butanesulphonamide, (4-aminobenzenesulphonyl)-p-toluenesulphonamide, (4-aminobenzenesulphonyl)-o-toluenesulphonamide, (4-aminobenzenesulphonyl)-methylsulphonamide, (4-aminobenzenesulphonyl)-butanesulphonamide, (4-amino-3-trifluoromethyl)-benzenesulphonyl)-benzenesulphonamide, (4-amino-3-trifluoromethyl)-benzenesulphonyl)-methanesulphonamide, (4-amino-3-trifluoromethyl)-benzenesulphonyl)-butanesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-p-toluenesulphonamide, (4-amino-4-trifluoromethyl-benzenesulphonyl)-o-toluenesulphonamide, (4-amino-3-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-3-chlorobenzenesulphonyl)-benzenesulphonamide, (4-amino-3-chlorobenzenesulphonyl)-p-toluenesulphonamide, (4-amino-3-chlorobenzenesulphonyl)-methanesulphonamide, (4-amino-3-chlorobenzenesulphonyl)-dimethylaminosulphonamide, (4-amino-3-bromobenzenesulphonyl)-benzenesulphonamide, (4-amino-3-methylbenzenesulphonyl)-benzenesulphonamide, (4-amino-3-methylbenzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dichlorobenzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dichlorobenzenesulphonyl)-propanesulphonamide, (4-amino-2,5-dichlorobenzenesulphonyl)-p-toluenesulphonamide, (4-amino-2,5-dichlorobenzenesulphonyl)-dimethylaminosulphonamide, (4-amino-3,5-diclorobenzenesulphonyl)-benzenesulphonamide, (4-amino-2-chloro-5-trifluoromethylbenzenesulphonyl)-benzenesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-2-chloro-5-trifluoromethyl-benzenesulphonyl)-2-naphthylsulphonamide, (4-amino-2-trifluoromethyl-5-chlorobenzenesulphonyl)-benzenesulphonamide, (4-amino-2-trifluoromethyl- 5-chlorobenzenesulphonyl)-2-naphthylsulphonamide, (4-amino-2-trifluoromethyl-5-bromobenzenesulphonyl)-butanesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-methanesulphonamide, (4-amino-2-trifluoromethyl-benzenesulphonyl)-butanesulphonamide, (4-amino-2-methyl-5-chlorobenzenesulphonyl)-p-toluenesulphonamide, (4-amino-2-methyl-5-chlorobenzenesulphonyl)-o-toluenesulphonamide, (4-amino-2,5-dibromobenzenesulphonyl)-benzenesulphonamide, (4-amino-2,5-dimethylbenzenesulphonyl)-butanesulphonamide, 2,4-dimethyl-5-sulpho-aniline, 4-ethoxy-5-sulpho-aniline, 4-phenoxy-5-sulphonaniline, N-(4-amino-phenylsulphonyl)-2-aminoethanesulphonic acid, N-methyl-N-(4-amino-phenylsulphonyl)-2-amino-ethanesulphonic acid, N-propyl-N-(4-amino-phenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-2-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-2-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-phenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-phenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-2-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-2-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-3-chlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-2,5-dichlorophenylsulphonyl)- 2-amino-ethanesulphonic acid, N-ethyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3,5-dichlorophenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3-methylphenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3-methoxyphenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3-methoxyphenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-amino-3-trifluoromethylphenylsulphonyl)-2-amino-ethanesulphonic acid, N-methyl-N-(4-amino-3-trifluoromethylphenylsulphonyl)-2-aminoethanesulphonic acid, N-propyl-N-(4-amino-3-trifluoromethylphenylsulphonyl)-2-amino-ethanesulphonic acid, N-(4-aminophenylsulphonyl)-3-amino-propylsulphonic acid, N-methyl-N-(4-amino-phenylsulphonyl)-3-amino-propylsulphonic acid, N-(4-amino-2-chlorophenylsulphonyl)-3-amino-propylsulphonic acid, N-(4-amino-2,5-dichlorophenylsulphonyl)-3-amino-propylsulphonic acid, N-(4-amino-3,5-dichlorophenylsulphonyl)-3-amino-propylsulphonic acid, N-propyl-N-(4-amino-3,5-dichlorophenylsulphonyl)-3-amino-propylsulphonic acid, N-(4-amino-3-trifluoromethylphenylsulphonyl)-3-amino-propylsulphonic acid, N-methyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-3-amino-butylsulphonic acid, N-(4-amino-2,5-dichlorophenylsulphonyl)-3-amino-phenylsulphonic acid, N-(4-amino-3-trifluoromethylphenylsulphonyl)-3-aminophenylsulphonic acid, N-(4-amino-2,5-dichlorophenylsulphonyl)-4-amino-phenylsulphonic acid, N-methyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-4-amino-phenylsulphonic acid, N-(4-amino-2,5-dichlorophenyl)-sulphonyl- 2-amino-ethyl sulphate, N-methyl-N-(4-amino-2,5-dichlorophenylsulphonyl)-2-amino-ethyl sulphate, N-ethyl-N-(4-amino-2-dichlorophenylsulphonyl)-2-amino-ethyl sulphate, N-(4-amino-phenylsulphonyl)-2-amino-ethyl sulphate, N-methyl-N-(4-amino-phenylsulphonyl)-2-amino-1-methyl ethyl sulphate, 4-(2-sulphatoethoxy)-aniline, 4-(2-sulphatopropoxy)-aniline, 4-(3-sulphato-4-phenoxy-n-butoxy)-aniline, 2-methyl-4-(2-sulphato-2-phenylethoxy)-aniline, 2-methyl-4-(3-sulphato-4-methoxy-n-butoxy)-aniline, 4-(2-sulphato-1,2-dimethylethoxy)-aniline, 3-(2-sulphato-3-ethoxy-propoxy)-aniline and 3-(2-sulphato-3-butoxy-propoxy)-aniline.
Examples of suitable thiazoles are: 2-aminothiazole, 2-amino-4-methyl-thiazole, 2-amino-4-phenyl-thiazole, 2-amino-4-ethyl-thiazole, 2-amino-4-(o-tolyl)-thiazole, 2-amino-4-(sulphophenyl)-thiazole, 2-amino-4-(4-nitrophenyl)-thiazole, 2-amino-4-(3-nitrophenyl)-thiazole, 2-amino-4-carbethoxythiazole and 2-amino-4-chlorothiazole.
Examples of suitable coupling components for the diazotised monoazo dyestuffs are: N,N-diethylaniline, N,N-dipropylaniline, N,N-dibutylaniline, 3-methyl-N,N-diethylaniline, 3-methyl-N-ethyl-N-(2-cyanoethyl)-aniline, 3-methyl-N-ethyl-N-(2-methyl-carbonyloxyethyl)-aniline, 3-methyl-N-(2-methyloxycarbonyloxyethyl)-N-ethyl-aniline, 3-ethyl-N,N-diethylaniline, 3-methyl-N,N-di-(2-ethoxycarbonyloxyethyl)-aniline, 3-methyl-N,N-di-(2-butoxycarbonyloxyethyl)-aniline, 2-acetylamino-N,N-diethylaniline, 2-acetylamino-N-ethyl-N-(2-ethoxycarbonyloxyethyl)-aniline, 3-acetylamino-N-ethyl-N-(2-cyanoethyl)-aniline, 3-acetylamino-N-(2-cyanoethyl)-N-(2-carbethoxycarbonyloxyethyl)-aniline, 3-(propylcarbonylamino)-N,N-diethylaniline, 3-(methylsulphonylamino)-N,N-diethylaniline, 3-(butylsulphonylamino)-N,N-diethylaniline, 3-(phenylsulphonylamino-N,N-diethylaniline, 3-acetylamino-6-ethoxy-N,N-diethylaniline, 3-acetylamino-6-methoxy-N,N-diethylaniline, 3-acetylamino-6-methoxy-N-ethyl-N-(2-cyanoethyl)-aniline, 3-acetylamino-6-methoxy-N,N-di-(2-ethoxycarbonyloxyethyl)-aniline, 3-chloro-N,N-diethylaniline, 3-chloro-N,N-dimethylaniline, 3-chloro-N-ethyl-N-(2-(cyanoethyl)-aniline, 2-carbamoyl-N,N-diethylaniline, 2-carbethoxy-N,N-diethylaniline, N-ethyl-N-(2-sulphoethyl)-aniline, 3-methyl-N-ethyl-N-(2-sulphoethyl)-aniline, 3-methyl-N-benzyl-N-(2-sulphoethyl)-aniline, 3-methyl-N-ethyl-N-(3-sulphobenzyl)-aniline, N-ethyl-N-(3-sulphobenzyl)-aniline, 3-methyl-N-methyl-N-(3-sulphobenzyl)-aniline, 3methoxy-N-ethyl-N-(3-sulphobenzyl)-aniline, 3-acetoamino-N-butyl-N-(3-sulphobenzyl)-aniline, 8-anilinonaphthalene-1-sulphonic acid, 8-p-toluidinonaphthalene-1-sulphonic acid, N,N-diethyl-8-aminonaphthalene-1-sulphonic acid, N,N-diethyl-5-aminonaphthalene-2-sulphonic acid, N-ethyl-N-(2-cyanoethyl)-5-aminonaphthalene-2-sulphonic acid, indole, 1-methylindole, 3-methylindole, 2-phenylindole, 2-ethylindole, 1-methyl-2-phenylindole, 2-phenylindolesulphonic acid, 1-methylindolesulphonic acid, 1-(2-hydroxypropyl)-2-methylindole, 1-(2-hydroxybutyl)-2-methylindole, 1-(2-hydroxy-2-phenylethyl)-2-methylindole, 1-(2-hydroxy-2-methyl-propyl)-2-methylindole, 1-(2-hydroxy-3-phenoxy-propyl)-2-methylindole, 1-(1-hydroxypropyl-2)-2-methylindole, 1-(2-hydroxypropyl)-2-phenylindole, 1-(2-hydroxy-butyl)-2-phenylindole, 1-(2-hydroxy-2-phenylethyl)-2-phenylindole, 1-(2-hydroxy-2-methyl-propyl)-2-phenylindole, 1-(2-hydroxy-3-phenoxy-propyl)-2-phenylindole, 1-( 1-hydroxypropyl-2)-2-phenylindole, 1-(2-hydroxypropyl)-2-methylindolesulphonic acid, 1-(2-hydroxy-butyl-2-methylindolesulphonic acid, 1-(2-hydroxy-2-phenylethyl)-2-methylindolesulphonic acid, 1-(2-hydroxy-2-methyl-propyl)-2-methylindolesulphonic acid, 1-(2-hydroxy-3-phenoxy-propyl)-2-methylindolesulphonic acid, 1-(1-hydroxy-propyl-2)-2-methylindolesulphonic acid, 1-(2-hydroxypropyl)-2-phenylindolesulphonic acid, 1-(2-hydroxybutyl)-2-phenylindolesulphonic acid, 1-(2-hydroxy-2-phenylethyl)-2-phenylindolesulphonic acid, 1-(2-hydroxy-2-methylpropyl)-2-phenylindolesulphonic acid, 1-(2hydroxy-3-phenoxypropyl)-2-phenylindolesulphonic acid and 1-(1-hydroxypropyl-2)-2-phenylindolesulphonic acid.
3-Methyl-5-pyrazolone, 1-phenyl-3-methyl-5-pyrazolone, 1-(2-chlorophenyl)-3-methyl-5-pyrazolone, 1-(2,5-dichlorophenyl)-3-methyl-5-pyrazolone, 1-p-tolyl-3-ethyl-5-pyrazolone, 1-(3-sulphamoyl-phenyl)-3-methyl-5-pyrazolone, 1-(2-sulphophenyl)-3-methyl-5-pyrazolone, 1-(3-sulphophenyl)-3-methyl-5-pyrazolone, 1-(6-chloro-3-sulphophenyl)-3-methyl-5-pyrazolone, 1-(3-sulphophenyl)-5-amino-3-methylpyrazolone, 1-(4-sulphophenyl)-3-methyl-5-pyrazolone, 1-(2-chloro-4-sulphophenyl)-3-methyl-5-pyrazolone, 1-(2,5-dichloro-4-sulphophenyl)-3-methyl-5-pyrazolone, 1-(6-chloro-4-sulphone-2-methylphenyl)-3-methyl-5-pyrazolone, 1-(6-chloro-4sulpho-2-ethyl-phenyl)-5-amino-3-methylpyrazole, 1-(2-sulphophenyl)-5-amino-3-methylpyrazole, 1-(3-sulphophenyl)-5-amino-3-ethylpyrazole, 1-(4-sulphophenyl)-5-amino-3-methylpyrazole, 1-phenyl-3-methyl-5-aminopyrazole, 1-(2-sulphophenyl)-3-phenyl-5-pyrazolone, 1-phenyl-3-phenyl-5-pyrazolone, 1-(3-sulphophenyl)-3-(4 -nitrophenyl)-5-pyrazolone, 1-phenyl-5-pyrazolone-3-carboxylic acid ethyl ester, 1-phenyl-5-pyrazolone-3-carboxylic acid amide, 1-(6-chloro-4-sulpho-2-methylphenyl)-5-pyrazolone-3-carboxylic acid ethyl ester, 1,4-dimethyl-5-cyano-2-hydroxy-6-pyridone, 1-propyl-4-methyl-5-cyano-2-hydroxy-6-pyridone, 1-butyl-4-ethyl-5-carbamoyl-2-hydroxy-6-pyridone, 1-ethyl-4-methyl-5-carbethoxy-2-hydroxy-6-pyridone, 1-methyl-4,5-dicarbomethoxy-2-hydroxy-6-pyridone and 1-propyl-2,4-dihydroxypyridione-6-pyridone.
The dyestuffs according to the invention can be used for dyeing natural and synthetic fibre materials, especially for dyeing polyamide in level, violet to blue-green shades of good colour yield and good fastness properties in use. They are absorbed well on polyamide even in a neutral to weakly acid dyebath. By polyamide fibres there are in particular to be understood, in this context, those of synthetic polyamides such as .epsilon.-polycaprolactam or condensation products of adipic acid and hexamethylenediamine.

EXAMPLE 1
3.5 g of 4-ethoxy-3-sulphoaniline and 1 g of NaNO.sub.2 are together dissolved in 20 ml of 3% strength of sodium hydroxide solution. The solution is then poured onto 20 g of ice and 10 ml of concentrated hydrochloric acid and the mixture is stirred for a further 2 hours at 0.degree. C.
2.6 g of 4-phenyl-2aminothiazole are dissolved in 25 ml of glacial acetic acid. This solution is allowed to run into 100 ml of saturated sodium acetate solution and 50 g of sodium acetate and 50 g of ice are added. The diazonium salt solution prepared above is rapidly poured in at 0.degree. C. The dyestuff which has precipitated, of the formula ##STR13## is filtered off, dried and then dissolved in 15 ml of dimethylformamide. The dyestuff solution is introduced into 50 ml of phosphoric acid and 30 ml of glacial acetic acid and is cooled to 5.degree. C. Diazotisation is carried out with 5.6 ml of 40% strength nitrosylsulphuric acid. After 3 hours, 4 g of urea are added and 3.5 g of N-cyanoethyl-N-phenylethyl-m-toluidine dissolved in 30 ml of glacial acetic acid are then allowed to run into the diazonium salt solution.
The reaction mixture is introduced into 200 ml of saturated sodium acetate solution and 200 g of ice. The dyestuff which has precipitated, of the formula ##STR14## is filtered off and dried at 40.degree. C.
DYEING EXAMPLE
0.1 g of dyestuff from Example 1 is dissolved in 100 ml of hot water. 5 ml of ammonium acetate solution are added and the mixture is diluted with water to a volume of 500 ml. 10 g of polyamide fibres are introduced into this dyebath, the dyebath is brought to the boil over the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the bath is kept at this temperature for 1 hour. The fibres are then rinsed, and dried at 70.degree. to 80.degree. C. A dyeing in a greenish-tinged navy blue shade, having good fastness properties in use, is obtained.
EXAMPLE 2
2.3 g of 2,4-dichloroaniline are stirred into 70 ml of half-concentrated hydrochloric acid and 1 g of NaNO.sub.2, dissolved in 10 ml of water, is added at 0.degree. C. The mixture is stirred for a further 2 hours at 0.degree. C.
2.6 g of 4-phenyl-2-aminothiazole are dissolved in 25 ml of glacial acetic acid. The solution is allowed to run into 100 ml of saturated sodium acetate solution and 50 g of sodium acetate and 50 g of ice are added. The diazonium salt solution prepared above is added rapidly at 0.degree. C. The dye-stuff which has precipitated, of the formula ##STR15## is filtered off and dried at 40.degree. C. The finely ground dyestuff is dissolved in 20 ml of phosphoric acid and 20 ml of glacial acetic acid and 5.6 g of 40% strength natrosylsulphuric acid are added at 0.degree. C. The mixture is then stirred for about 3 hours. Thereafter 4 g of urea are added to the diazonium salt solution, after which 3.5 g of N-ethyl-N-sulphobenzyl-m-toluidine, dissolved in 30 ml of glacial acetic acid, are added to the reaction mixture. The solution is stirred for a further 5 minutes and is then introduced into 200 ml of sodium acetate solution and 200 g of ice. The dyestuff which has precipitated, of the formula ##STR16## is filtered off and dried at 40.degree. C.
The dyestuff dyes polyamide in a greenish-tinged navy blue colour shade.
If the procedure in Example 1 and 2 is followed, using the amines indicated in column 1 as a diazo component, 2-amino-4-phenylthiazole as the middle component and the compounds indicated in column 2 as the coupling component, water-soluble dyestuffs are obtained, which dye polyamide, from a weakly acid or neutral bath, in the light-fast colour shades which are indicated.
__________________________________________________________________________I II III__________________________________________________________________________3) Metanilic acid N-ethyl-N-cyanoethyl-m-toluidine greenish-tinged blue4) Metanilic acid N-benzyl-N-cyanoethyl-m-toluidine greenish-tinged blue5) Metanilic acid N,N-diethyl-m-toluidine strongly greenish- tinged blue6) Metanilic acid N-ethyl-N-benzyl-m-toluidine strongly greenish- tinged blue7) Metanilic acid N-ethyl-N-(2-acetoxy-ethyl)-m-toluidine greenish-tinged blue8) Metanilic acid N-(2-cyanoethyl)-N-(2-phenylethyl)- greenish-tinged blue m-toluidine9) 4-Methyl-3-sulphoaniline N-(2-cyanoethyl)-N-(2-phenethyl)-m-toluidine greenish-tinged blue10) 3-Sulpho-4-methylaniline N-(2-methoxycarbonylethyl)-N-ethyl-3- greenish-tinged blue methylaniline11) 3-Sulpho-4-methylaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue12) 3-Sulpho-4,6-dimethylaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline13) 3-Sulpho-4,6-dimethylaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue14) 3-Sulpho-4,6-dimethylaniline N-(2-methoxycarbonyloxyethyl)-N-ethyl-3- greenish-tinged blue methylaniline15) 3-Sulpho-4,6-dimethylaniline N,N-diethyl-3-acetylaminoaniline green-blue16) 3-Sulpho-4,6-dimethylaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue17) 3-Sulpho-4-ethoxyaniline N-(2-methylsulphonylethyl)-N-ethyl-3- greenish-tinged blue methylaniline18) 3-Sulpho-4-ethoxyaniline N-(2-acetoxyethyl)-N-ethyl-3-methylaniline greenish-tinged blue19) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue methylaniline20) 3-Sulpho-4-ethoxyaniline N-(2-hydroxyethyl)-N-benzyl-3-methylaniline greenish-tinged blue21) 3-Sulpho-4-ethoxyaniline N-(2-hydroxyethyl)-N-ethyl-3-methylaniline greenish-tinged blue22) 3-Sulpho-4-ethoxyaniline N,N-di-(2-methoxycarbonyloxyethyl)-3- greenish-tinged blue methylaniline23) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue24) 3-Sulpho-4-ethoxyaniline N-(2-phenylethyl)-3-methylaniline greenish-tinged blue25) 3-Sulpho-4-ethoxyaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue26) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue27) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-N-(2-acetoxyethyl)-3- greenish-tinged blue methylaniline28) 3-Sulpho-4-ethoxyaniline N,N-diethyl-3-methoxyaniline greenish-tinged blue29) 3-Sulpho-4-ethoxyaniline N,N-diethyl-3-acetylaminoaniline green-blue30) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue31) 3-Sulpho-4-ethoxyaniline N-(2-chloroethyl)-N-ethyl-3-methylaniline greenish-tinged blue32) 3-Sulpho-4-ethoxyaniline N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue33) 3-Sulpho-4-ethoxyaniline N-(2-hydroxyethyl)-N-benzyl-3-acetylamino- green-blue aniline34) 3-Sulpho-4-ethoxyaniline N-benzyl-N-ethyl-3-acetylaminoaniline green-blue35) 2-Ethoxy-5-sulphoaniline N-ethyl-N-benzyl-3-acetylaminoaniline green-blue36) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue37) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-benzyl-3-methylaniline greenish-tinged blue38) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline39) 2-Ethoxy-5-sulphoaniline N-(2-acetoxyethyl)-N-ethyl-3-methylaniline greenish-tinged blue40) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-(2-acetoxyethyl)-3- greenish-tinged blue methylaniline41) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue methylaniline42) 2-Ethoxy-5-sulphoaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue43) 2-Ethoxy-5-sulphoaniline N-(2-methylsulphonylethyl)-N-ethyl-3- greenish-tinged blue methylaniline44) 2-Ethoxy-5-sulphoaniline N,N-di-(2-methoxycarbonyloxyethyl)-3- greenish-tinged blue methylaniline45) 2-Ethoxy-5-sulphoaniline N-(2-phenylethyl)-N-ethyl)-3-methylaniline greenish-tinged blue46) 2-Ethoxy-5-sulphoaniline N-(2-p-methoxyphenylethyl)-N-ethyl-3- greenish-tinged blue methylaniline47) 2-Ethoxy-5-sulphoaniline N-(2-phenylethyl)-aniline greenish-tinged blue48) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue49) 2-Ethoxy-5-sulphoaniline N-(2-hydroxyethyl)-N-ethyl)-3-methylaniline greenish-tinged blue50) 2-Ethoxy-5-sulphoaniline N-(2-phenylsulphonylethyl)-N-ethyl-3- greenish-tinged blue methylaniline51) 2-Ethoxy-5-sulphoaniline N-(2-chloroethyl)-N-ethyl-3-methylaniline greenish-tinged blue52) 2-Ethoxy-5-sulphoaniline N,N-diethyl-3-acetylaminoaniline greenish-tinged blue53) 3-Sulpho-4-phenoxyaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue54) 3-Sulpho-4-phenoxyaniline N-(2-phenylethyl)-N-ethyl-3-methylaniline greenish-tinged blue55) 3-Sulpho-4-phenoxyaniline N-(2-phenylethyl)-N-(2-cyanoethyl)-3- greenish-tinged blue methylaniline56) 3-Sulpho-4-phenoxyaniline N-(2-cyanoethyl)-N-benzyl-3-methylaniline greenish-tinged blue57) 3-Sulpho-4-phenoxyaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue58) 3-Sulpho-4-phenoxyaniline N-(2-acetoxyethyl)-N-ethyl-3-methylaniline greenish-tinged blue59) 3-Sulpho-4-phenoxyaniline N-(2-methylsulphonylethyl)-N-ethyl-3- greenish-tinged blue methylaniline60) 3-Sulpho-4-phenoxyaniline N-(2-hydroxyethyl)-N-(2-cyanoethyl)-3- greenish-tinged blue methylaniline61) 3-Sulpho-4-phenoxyaniline N-(2-hydroxyethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline62) 3-Sulpho-4-phenoxyaniline N-(2-cyanoethyl)-N-ethylaniline greenish-tinged blue63) 3-Sulpho-4-phenoxyaniline N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue64) 3-Sulpho-4-phenoxyaniline N-(2-phenylethyl)-3-methylaniline greenish-tinged blue65) 2-Methyl-5-sulphoaniline N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue66) 2-Methyl-5-sulphoaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline67) 2-Methyl-5-sulphoaniline N-(2-cyanoethyl)-N-benzyl-3-methylaniline greenish-tinged blue68) 2-Methyl-5-sulphoaniline N-(2-hydroxyethyl)-N-(2-cyanoethyl)-3- greenish-tinged blue methylaniline69) 2-Methyl-5-sulphoaniline N-(2-acetoxyethyl)-N-ethyl-3-methylaniline greenish-tinged blue70) 2-Methyl-5-sulphoaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue71) 2-Methyl-5-sulphoaniline N-(2-hydroxyethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline72) 2-Methyl-5-sulphoaniline N-(2-hydroxyethyl)-N-benzylaniline greenish-tinged blue73) 2-Methyl-5-sulphoaniline N,N-diethyl-2-methyl-5-acetylaminoaniline blue-green74) 2-Methyl-5-sulphoaniline N-(2-hydroxyethyl)-N-ethyl-3-acetylamino- blue-green aniline75) 2-Methyl-5-sulphoaniline N-ethyl-N-benzyl-3-acetylaminoaniline blue-green76) 2-Methyl-4-sulphoaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue77) 2-Methyl-4-sulphoaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline78) 2-Methyl-4-sulphoaniline N-(2-cyanoethyl)-N-benzylaniline greenish-tinged blue79) 3-Amino-benzenesulphonic N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue acid N-methyl-N-(2- sulphoethyl)-amide80) 3-Amino-benzenesulphonic N-(2-chloroethyl)-N-(2-cyanoethyl)-aniline greenish-tinged blue acid N-methyl-N-(2- sulphoethyl)-amide81) 3-Amino-4-methylsulphonic N-(2-hydroxyethyl)-N-(2-cyanoethyl)-3- greenish-tinged blue acid N-(2-sulphoethyl)- ethylaniline amide82) 3-Amino-4-methylsulphonic N-(2-cyanoethyl)-N-(2-phenylethyl)-2- greenish-tinged blue acid N-(2-sulphoethyl)- ethoxyaniline amide83) 3-Amino-4-methylsulphonic N-(2-acetoxyethyl)-N-(2-cyanoethyl)-2- blue-green acid N-(2-sulphoethyl)- methoxy-5-methylaniline amide84) 3-Amino-4-ethoxybenzene- 1-benzylaminonaphthalene greenish-tinged blue sulphonic acid N-methyl- N-(2-sulphoethyl)-amide85) 3-Amino-4-ethoxybenzene- N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue sulphonic acid N-methyl- N-(2-sulphoethyl)-amide86) 3-Amino-4-methoxybenzene- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue sulphonic acid N-methyl- methylaniline N-(2-sulphoethyl)-amide87) 3-Amino-4-methoxybenzene- N,N-di-(2-ethoxycarbonyloxyethyl)-3- greenish-tinged blue sulphonic acid N-methyl- methylaniline N-(2-sulphoethyl)-amide88) 3-Benzenesulphonylamino- N,N-di-(2-ethoxycarbonyloxyethyl)-3- blue sulphonylaniline methylaniline89) 3-Benzenesulphonylamino- N,N-diethyl-3-methylaniline greenish-tinged blue sulphonylaniline90) 3-Benzenesulphonylamino- N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue sulphonylaniline91) 3-Benzenesulphonylamino- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue sulphonylaniline methylaniline92) 3-Benzenesulphonylamino- N-(2-cyanoethyl)-N-benzyl-3-methylaniline greenish-tinged blue sulphonylaniline93) 3-Benzenesulphonylamino- 1-phenyl-3-methyl-5-pyrazolone violet sulphonylaniline94) 3-Benzenesulphonylamino- 1-(2,5-dichlorophenyl)-3-methyl-5-pyrazolone violet sulphonylaniline95) 3-Benzenesulphonylamino- 1-(2-methylphenyl)-3-methyl-5-pyrazolone violet sulphonylaniline96) 3-Methylsulphonylamino- N-ethyl-N-(2-propylcarbonyloxyethyl)-3- greenish-tinged blue sulphonylaniline methylaniline97) 3-Methylsulphonylamino- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue sulphonylaniline methylaniline98) 3-Methylsulphonylamino- N-(2-cyanoethyl)-N-)2-hydroxyethyl)-3- greenish-tinged blue sulphonylaniline methylaniline99) 3-Methylsulphonylamino- N-(2-cyanoethyl)-N-benzyl-3-methylaniline greenish-tinged blue sulphonylaniline100) 3-Methylsulphonylamino- N-(2-cyanoethyl)-N-ethyl-3-methylaniline greenish-tinged blue sulphonylaniline101) 3-Methylsulphonylamino- 2-phenylindole violet sulphonylaniline102) 2-Ethoxy-5-(2-methylphenyl)- 2-phenylindole violet sulphonylamino-sulphonyl- aniline103) 2-Ethoxy-5-(2-methylphenyl)- N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue sulphonylamino-sulphonyl- methylaniline aniline104) 2-Ethoxy-5-(2-methylphenyl)- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue sulphonylamino-sulphonyl- methylaniline aniline105) 2-Ethoxy-5-(2-methylphenyl)- m-cresol violet sulphonylamino-sulphonyl- aniline106) 2-Ethoxy-5-(2-methylphenyl)- o-cresol violet sulphonylamino-sulphonyl- aniline107) 2-Ethoxy-5-phenylsulphonyl- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue amino-sulphonylaniline methylaniline108) 2-Ethoxy-5-phenylsulphonyl)- N-ethyl-N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue amino-sulphonylaniline109) 2-Ethoxy-5-phenylsulphonyl- N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue amino-sulphonylaniline methylaniline110) 2-Ethoxy-5-phenylsulphonyl- N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue amino-sulphonylaniline111) 2-Ethoxy-5-phenylsulphonyl- m-cresol violet amino-sulphonylaniline112) 2-Ethoxy-5-phenylsulphonyl- p-cresol violet amino-sulphonylaniline113) 2-Ethoxy-5-phenylsulphonyl- 1,4-dimethyl-2-hydroxy-5-cyano-6-pyridone violet amino-sulphonylaniline114) 2-Ethoxy-5-phenylsulphonyl- 1-propyl-2-hydroxy-4-methyl-5-cyano- violet amino-sulphonylaniline 6-pyridone115) 2-Methyl-5-(4-chlorophenyl)- 1-phenyl-2-hydroxy-4-ethyl-5-cyano- violet sulphonylamino-sulphonyl- 6-pyridone aniline116) 2-methyl-5-(4-chlorophenyl)- 2-hydroxy-4-methyl-dimethylaminocarbonyl- violet sulphonylamino-sulphonyl- 6-pyridone aniline117) 2-Methyl-5-phenylsulphonyl- N-butyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue aminosulphonylaniline118) 2-Methyl-5-phenylsulphonyl- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue aminosulphonylaniline methylaniline119) 2-Methyl-5-phenylsulphonyl- N-ethyl-N-(2-acetoxyethyl)-aniline greenish-tinged blue aminosulphonylaniline120) 2-Methyl-5-phenylsulphonyl- N-propyl-N-benzyl-3-methylaniline greenish-tinged blue aminosulphonylaniline121) 2-Methyl-5-phenylsulphonyl- N,N-diethyl-3-methylsulphonylaminoaniline strongly greenish- aminosulphonylaniline tinged blue122) 2-Methyl-5-phenylsulphonyl- N-ethyl-N-(2-hydroxyethyl)-3-phenyl- strongly greenish- aminosulphonylaniline sulphonylaminoaniline tinged blue123) 4-Phenylsulphonylamino- 1-phenyl-3-methyl-5-aminopyrazole blue-violet sulphonylaniline124) 4-Phenylsulphonylamino- 1-(4-chlorophenyl)-3-ethyl-5-aminopyrazole blue-violet sulphonylaniline125) 2-Methyl-4-phenylsulphonyl- N,N-di-(2-cyanoethyl)-3-butyrylaminoaniline green-blue aminosulphonylaniline126) 2-Methyl-4-phenylsulphonyl- N-ethyl-N-(2-hydroxyethyl)-2,5-dimethyl- strongly greenish- aminosulphonylaniline aniline tinged blue127) 3-Sulpho-4-(2-nitrophenoxy) N-ethyl-N-benzyl-3-ethoxyaniline greenish-tinged blue aniline128) 3-Sulpho-4-(2-ethylphenoxy)- N,N-diethyl-3-benzoylaminoaniline green-blue aniline129) 2-Chloro-5-sulphoaniline 1-(2-methyl-5-chlorophenyl)-3-ethyl-5- violet aminopyrazole130) 2,5-Dichloro-4-sulphoaniline 1-(2,4-dichlorophenyl)-3-methyl-5- violet aminopyrazole131) 2-Bromo-5-sulphoaniline N-ethyl-N-benzylaniline greenish-tinged blue132) 2-Chloro-5-phenylsulphonyl- N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue aminosulphonylaniline133) 4-(2-Sulphatoethyoxy)-aniline N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue134) 2-Methyl-4-(2-sulphato- N,N-dibenzyl-3-methylaniline greenish-tinged blue propoxy)-aniline135) 2-Chloro-4-(2-sulphato- N-(2-cyanoethyl)-N-(4-methoxybenzyl)-3- greenish-tinged blue butoxy)-aniline methylaniline136) 4-(2-Sulphato-2-phenyl- N-(2-cyanoethyl)-N-(4-methoxybenzyl)-3- greenish-tinged blue ethoxy)-aniline methylaniline137) 2-Bromo-5-(2-sulphato- N-benzyl-N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue ethoxy)-aniline138) 2-Methoxy-5-(2-sulphato- N-ethyl-N-(3-nitrobenzyl)-3-methylaniline greenish-tinged blue 2-phenylethoxy)-aniline139) 1-Amino-8-sulphonaphthalene N-(2-cyanoethyl)-N-(2-phenylethyl)-3- green-blue methylaniline140) 1-Amino-6-sulphonaphthalene N-(2-chloroethyl)-N-(2-cyanoethyl)-3- greenish-tinged blue methylaniline141) 1-Amino-6-sulphonaphthalene 1-phenyl-3-methyl-pyrzolone blue-violet142) 1-Amino-6-sulphonaphthalene N,N-diethyl-3-propionyl-aminoaniline green-blue143) 1-Amino-4-sulphoaniline N,N-diethyl-2-methylaniline green-blue144) 2-Methyl-4-chloroaniline N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue145) 2,4-Dichloroaniline N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue146) 2-Chloro-4-ethoxyaniline N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue147) 3-Phenylaminosulphonyl- N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue aniline148) 3-Diethylaminosulphonyl- N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue aniline149) 2-Ethoxy-5-diethylamino- N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue sulphonylaniline150) 2-Ethoxy-5-diethylamino- N-ethyl-N-(3-sulphobenzyl)-3-methylaniline greenish-tinged blue sulphonylaniline151) 3-Dipropylaminosulphonyl- N-benzyl-N-(2-sulphoethyl)-3-methylaniline greenish-tinged blue 4-ethylaniline152) 3-(2-phenylethylamino)- N-benzyl-N-(2-sulphoethyl)-3-methylaniline greenish-tinged blue sulphonyl-4-propoxyaniline153) 4-Methylsulphonylaniline N-benzyl-N-(2-sulphoethyl)-3-methylaniline greenish-tinged blue154) 2-Ethoxy-4-diethylamino- N-benzyl-n-(2-sulphoethyl)-3-methylaniline greenish-tinged blue sulphonylaniline155) 2-Trifluoromethyl-4- N-benzyl-N-(2-sulphoethyl)-3-methylaniline greenish-tinged blue chloroaniline156) 2-Propoxy-5-phenylamino- 1-(4-methylphenylamino)-8-sulphonaphthalene blue-green sulphonylaniline157) 4-Sulphomethylaniline N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue158) 4-Sulphomethylaniline N-ethyl-N-(2-hydroxyethyl)-2,5-dimethyl- greenish-tinged blue aniline159) 4-Sulphomethylaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline160) 4-Sulphomethylaniline N-benzyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue161) 4-Sulphomethylaniline N-ethyl-N-(2-acetoxyethyl)-3-methylaniline greenish-tinged blue162) 4-Sulphomethylaniline N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue methylaniline163) 3-Sulphomethylaniline N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue methylaniline164) 3-Sulphomethylaniline N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue165) 3-Sulphomethylaniline N-ethyl-N-(2-phenylethyl)-methylaniline greenish-tinged blue166) 3-Sulphomethylaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline__________________________________________________________________________
If the procedure followed is as in Example 1 and 2, the amines indicated in column 1 of the table which follows are used as the diazo component, 2-amino-4-(x-sulphophenyl)-thiazole, which is obtained by sulphonation of 2-amino-4-phenylthiazole in accordance with customary methods, and the sulphonation position of which is not precisely established, is used as the middle component, and the compounds indicated in column 2 of the table which follows are used as the coupling component, further water-soluble dyestuffs are obtained, which dye polyamide from a weakly acid or neutral bath in the colour shades indicated.
__________________________________________________________________________I II III__________________________________________________________________________167) 2,5-Dichloroaniline N,N-diethyl-3-methylaniline greenish-tinged blue168) 3-Diethylaminosulphonyl- N-ethyl-N-(2-chloroethyl)-3-methylaniline greenish-tinged blue aniline169) 3-Phenylaminosulphonyl- N-ethyl-N-(2-chloroethyl)-3-methylaniline greenish-tinged blue aniline170) 3-Phenylaminosulphonyl- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue aniline methylaniline171) 3-Phenylaminosulphonyl- N-benzyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue aniline172) 3-Phenylaminosulphonyl)- N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue aniline173) 3-Aminosulphonylaniline N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue174) 2-Methyl-5-diethylamino- N-ethyl-N-(2-cyanoethyl)-3-methylaniline greenish-tinged blue sulphonylaniline175) 3-Dimethylaminosulphonyl- N-ethyl-N-benzyl-3-methylaniline greenish-tinged blue 4-methylaniline176) 2-Methoxy-5-diethylamino- N,N-di-(2-acetoxyethyl)-3-methylaniline greenish-tinged blue sulphonylaniline177) 3-Diethylaminosulphonyl- N,N-di-(2-acetoxyethyl)-methylaniline greenish-tinged blue 4-ethoxyaniline178) 2-Ethoxy-5-diethylamino- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue sulphonylaniline methylaniline179) 3-Benzylaminosulphonyl-4- N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue chloroaniline methylaniline180) 3-Methylsulphonylaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- greenish-tinged blue methylaniline181) 4-Phenylsulphonylaniline N-ethyl-N-(2-cyanoethyl)-2-methyl-5-ethoxy- strongly greenish- aniline tinged blue182) 4-Ethylsulphonylaniline N-ethyl-N-benzyl-2-methyl-5-ethylaniline strongly greenish- tinged blue183) 4-N-Methyl-N-benzylamino- N-ethyl-N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue sulphonylaniline184) 3-(2-phenylethyl)-amino- N-ethyl-N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue sulphonyl-4-phenoxyaniline185) 2,4-Dichloroaniline N-ethyl-N-(2-hydroxyethyl)-3-methylaniline greenish-tinged blue186) 2-Bromo-4-methylaniline N-ethyl-N-(2-cyanoethyl)-3-chloroaniline greenish-tinged blue187) 2,6-Dichloroaniline N-benzyl-3-methylaniline greenish-tinged blue188) 2-Methyl-4-chloroaniline N-(2-cyanoethyl)-N-(2-hydroxyethyl)-3- greenish-tinged blue methylaniline__________________________________________________________________________
EXAMPLE 189
If the procedure followed is as in Example 1, using 2-sulpho-4-aminodiphenyl as the diazo component, 2-amino-4-(2-methylphenyl)-thiazole as the middle component and N,N-diethyl-2,5-diethoxyaniline, a water-soluble dyestuff, which dyes polyamide greenish-tinged blue, is obtained.
If, in Example 189, the coupling component is replaced by N-ethyl-N-(2-cyanoethyl)-2-methyl-5-ethoxyaniline, a dyestuff which dyes polyamide greenish-tinged blue is obtained.
EXAMPLE 190
If the procedure followed is as in Example 1, using 2-sulpho-4-amino-2'-chlorodiphenyl as the diazo component, 2-amino-4-(3-nitrophenyl)-thiazole as the middle component and N,N-diethyl-2,5-dimethoxyaniline as the coupling component, a water-soluble dyestuff, which dyes polyamide greenish-tinged blue from a weakly acid bath, is obtained.
EXAMPLE 191
If the procedure followed is as in Example 1, using 2-sulpho-4-amino-4'-methoxydiphenyl as the diazo component, 2-amino-4-(4-methoxyphenyl)-thiazole as the middle component and N,N-diethyl-2-methoxy-5-butyrylaminoaniline as the coupling component, a dyestuff which dyes polyamide greenish-tinged blue is obtained.
EXAMPLE 192
Using 2-sulpho-4-amino-2'-nitrodiphenyl as the diazo component, 2-amino-4-(4-ethoxyphenyl)-thiazole as the middle component and N,N-diethylaniline as the coupling component, and following the procedure of Example 1, a dyestuff which dyes polyamide greenish-tinged blue is obtained.
EXAMPLE 193
Analogously to Example 1, a dyestuff which dyes polyamide a greenish-tinged blue is obtained when 2-sulpho-4-amino-4'-chlorodiphenyl oxide is used as the diazo component, 2-amino-4-(4-chlorophenyl)-thiazole as the middle component and N,N-diethylaniline as the coupling component.
EXAMPLE 194
If, in Example 193, the coupling component is replaced by 1-(2-cyanoethyl)-aminonaphthalene, a dyestuff which dyes polyamide green-blue from a weakly acid or neutral bath is obtained.
EXAMPLE 195
If the procedure of Example 1 is followed using 2-sulpho-4-amino-4'-ethoxydiphenyl oxide as the diazo component, 2-amino-4-(2-methoxyphenyl)-thiazole as the middle component and N-ethyl-N-(2-cyanoethyl)-3-methylaniline as the coupling component, a water-soluble dyestuff which dyes polyamide greenish-tinged blue, is obtained.
If the procedure followed is as in Example 1 and 2, using the amines indicated in column 1 of the formula which follows as the diazo component, 2-amino-4-methylthiazole as the middle component and the compounds indicated in column 2 of the table which follows as the coupling component, water-soluble dyestuffs, which dye polyamide, from a weakly acid or neutral bath, in the colour shades indicated, are obtained.
__________________________________________________________________________I II III__________________________________________________________________________196) 2-Ethoxy-5-sulphoaniline N-ethyl-N-(2-cyanoethyl)-3-methylaniline reddish-tinged blue197) 2-Ethoxy-5-sulphoaniline N-benzyl-N-(2-cyanoethyl)-3-methylaniline reddish-tinged blue198) 2-Ethoxy-5-sulphoaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- reddish-tinged blue methylaniline199) 3-Sulpho-4-ethoxyaniline N-(2-cyanoethyl)-N-(2-phenylethyl)-3- reddish-tinged blue methylaniline200) 3-Sulpho-4-ethoxyaniline N-ethyl-N-(2-cyanoethyl)-3-methylaniline reddish-tinged blue201) 3-Sulpho-4-ethoxyaniline 1-ethylaminoaniline reddish-tinged blue202) 3-Sulpho-4-ethoxyaniline 1-benzylaminonaphthalene greenish-tinged blue203) 2,4-Dimethyl-5-sulphoaniline N-ethyl-N-(2-acetoxyethyl)-3-methylaniline reddish-tinged blue204) 3-Sulpho-4-methylaniline N-ethyl-N-benzyl-3-methylaniline reddish-tinged blue205) 2-Methyl-5-sulphoaniline N-(2-hydroxyethyl)-N-2-cyanoethyl)-3- reddish-tinged blue methylaniline206) 2-Ethoxy-5-phenylsulphonyl- N-ethyl-N-[2-(2-chlorophenyl)-ethyl]-3- reddish-tinged blue aminosulphonyaniline methylaniline207) 2-Ethyl-5-ethylsulphonyl- N-propyl-N-[2-(2-methylphenyl)-ethyl]-3- reddish-tinged blue aminosulphonylaniline methylaniline208) 3-Phenylsulphonylamino- N-propyl-N-[2-(2-methylphenyl)-ethyl]-3- reddish-tinged blue sulphonyl-4-methoxyaniline methylaniline209) 4-[N-Ethyl-N-(2-sulpho- N-(2-cyanoethyl)-N-(2-hydroxypropyl)-3- reddish-tinged blue ethyl)-aminosulphonyl]- ethylaniline aniline210) 3-Sulpho-4-chloroaniline N-(2-phenylethyl)-N-(2-phenyl-2-hydroxy- reddish-tinged blue ethyl)-3-methylaniline211) 2-Methyl-5-(2-sulphato-3- N-ethyl-N-(2-cyanoethyl)-3-methylaniline reddish-tinged blue phenoxypropoxy)-aniline212) 2-Ethyl-4-diethylamino- N-benzyl-N-(2-sulphoethyl)-3-methylaniline reddish-tinged blue sulphonylaniline213) 2-Chloro-4-cyanoaniline N-benzyl-N-(2-sulphoethyl)-3-methylaniline reddish-tinged blue214) 3-Diethylaminocarbonyl- N-benzyl-N-(2-sulphoethyl)-3-methylaniline reddish-tinged blue aniline215) 3-Phenylsulphonylaniline N-benzyl-N-(2-sulphatoethyl)-3-methylaniline reddish-tinged blue216) 2-Ethylsulphonylaniline N-ethyl-N-(2-sulphatopropyl)-3-methylaniline reddish-tinged blue217) 4-Benzylsulphonylaniline N-(2-cyanoethyl)-N-(1-methyl-2-sulphato- reddish-tinged blue propyl)-aniline218) 2-Trifluoromethyl-4-methyl- N-ethyl-N-(2-phenyl-2-sulphatoethyl)-3- reddish-tinged blue sulphonylaniline methylaniline219) 2-Ethoxy-5-butylsulphonyl- N-(2-phenylethyl)-N-(2-sulphato-3-methoxy- reddish-tinged blue aniline propyl)-2-methoxy-5-methylaniline220) 4-Acetylaminoaniline N-butyl-N-(2-sulphato-3-phenoxypropyl)-3- reddish-tinged blue ethylaniline221) 2-Methyl-5-(2-phenylethyl)- N-ethyl-N-(3-sulphobenzyl)-3-acetylamino- reddish-tinged blue aminosulphonylaniline aniline__________________________________________________________________________
EXAMPLE 222
If the procedure followed is as indicated in Example 1, using 2,6-dichloroaniline as the diazo component, 2-aminothiazole as the middle component and 1-phenylamino-8-sulphonaphthalene as the coupling component, a water-soluble dye-stuff, which dyes polyamide blue from a weakly acid or neutral bath, is obtained.
EXAMPLE 223
A further blue polyamide dyestuff is obtained in accordance with the instructions of Example 1, using 2-methoxy-5-chloroaniline as the diazo component, 2-aminothiazole as the middle component and 6-diethylamino-3-sulphoaniline as the coupling component.
If the procedure followed is as in Example 1, using the amines indicated in column 1 of the formula which follows as the diazo component, 2-amino-4-ethylthiazole as the middle component and the compounds indicated in column 2 of the table which follows as the coupling component, water-soluble dye-stuffs, which dye polyamide, from a weakly acid or neutral bath, in the colour shades indicated, are obtained.
__________________________________________________________________________I II III__________________________________________________________________________224) 2,5-Dichloro-4-(2-sulphato- N,N-diethyl-2,5-dimethylaniline reddish-tinged blue ethoxy)-aniline225) 3-Methyl-4-(2-sulphato-3- N-(2-hydroxyethyl)-N-benzyl-2,5- reddish-tinged blue methoxypropoxy)-aniline dimethylaniline226) 2,6-Dimethyl-4-(2-sulphato- N-(2-cyanoethyl)-N-(2-hydroxyethyl)- reddish-tinged blue 3-ethoxypropoxy)-aniline 3-ethoxyaniline227) 2-Methoxy-5-methylsulphonyl- 1-(3-sulphophenyl)-3-ethyl-5-aminopyrazole violet aniline228) 2-Ethoxy-5-propylsulphonyl- 2-phenyl-x-sulphoindole violet aniline229) 2-Ethyl-5-propylsulphonyl- 1,2-dimethyl-x-sulphophenyl-indole violet aniline230) 3-Propylaminosulphonyl-4- 2-methyl-x-sulphoindole violet methylaniline231) 2-Chloro-4-methyl-5-dibutyl- 1-(3-sulphophenyl)-3-methyl-5-aminopyrazole violet aminosulphonylaniline232) 3-Diethylcarbonylaniline 1-(2,5-dichloro-4-sulphophenyl)-3- violet methyl-5-pyrazolone233) 3-Chloro-4-(2-sulphato- N-propyl-N-(2-cyanoethyl)-3-methylaniline reddish-tinged blue ethoxy)-aniline234) 3-Bromo-4-(2-sulphato- 1-ethylaminonaphthalene blue propoxy)-aniline235) 3-Chloro-4-(1-methyl-2- 1-ethylaminonaphthalene blue sulphatopropoxy)-aniline236) 3-Chloro-5-(1-methyl-2- N-(2-cyanoethyl)-N-(2-acetoxyethyl)-3- reddish-tinged blue sulphatopropyl)-aniline methylaniline237) 4-(1-Methyl-2-sulphato-3- N-(2-cyanoethyl)-N-(2-acetoxyethyl)-3- reddish-tinged blue phenoxypropoxy)-aniline methylaniline238) 1-Amino-5-sulphonaphthalene N-(2-cyanoethyl)-N-(2-acetoxyethyl)-3- blue methylaniline__________________________________________________________________________

Number	Name	Date	Kind
3134761	Ackermann et al.	May 1964
3134766	Merian et al.	May 1964

Number	Date	Country
910,385	Nov 1962	GBX
1,186,753	Apr 1970	GBX

Disazo dyestuffs containing a thiazole central component

Information

Patent Number

Date Filed

Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

US Classifications

Field of Search

US

International Classifications

Abstract

Description

Claims

Priority Claims (1)

US Referenced Citations (2)

Foreign Referenced Citations (2)