2-Amino-5-arylazoarylazothiazole compounds

Claim 2

A light fast and wet fast acid azo-dye containing a thiazole coupling component and having the formula: ##STR161## wherein D is phenyl or naphthyl substituted by arylazo, R is C 1 -C 4 -alkyl, β-carboxymethyl, or phenyl which is unsubstituted or substituted by chlorine, bromine, methyl, ethyl, C 1 -C 4 -alkoxy, β-cyanoethyl, β-carboxylethoxy, phenoxy, sulophenoxy, C 1 -C 4 -alkanoylamino, phenylamino, sulfophenylamino, sulfoethylamino, or hydroxysulfonyl and R 1 and R 2 independently of one another are C 1 -C 8 -alkyl, C 2 -C 8 -alkyl which is substituted by hydroxyl, carboxyl, hydroxysulfonyl, cyano, phenyl, C 1 -C 8 -alkoxy, phenoxy, C 1 -C 4 -alkanoyloxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkanoylamino or C 1 -C 4 -alkoxycarbonyloxy, allyl, phenyl-C 1 -C 5 -alkyl or phenyl which is unsubstituted or substituted by chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, cyano, carbamoyl, or hydroxysulfonyl.

Claim 3

The azo dye of claim 1, of the formula: ##STR162## where n is 0 or 1, R 3 is C 1 -C 4 -alkyl and D, R 1 and R 2 have the meanings given in claim 1.

Claim 4

A light fast and wet fast acid azo dye containing a thiazole coupling component and having the formula: ##STR163## wherein D is phenyl or naphthyl substituted by arylazo, R is acetyl; benzoyl; C 1 -C 4 -alkyl; C 1 -C 4 alkyl substituted by chlorine, bromine, cyano, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylmercapto, phenoxy, sulfophenoxy, phenylmercapto, amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, phenylamino, sulfophenylamino, C 1 -C 4 -alkanoylamino or sulfoethylamino; vinyl; cyclohexyl; phenyl; thienyl; thiazolyl; or phenyl, thienyl or thiazolyl substituted by fluorine, chlorine, bromine, hydroxyl, C 1 -C 4 -alkoxy, β-C 1 -C 4 -alkanoyloxyethoxy, β-cyanoethoxy, β-carboxylethoxy, β-C 1 -C 4 -alkoxycarbonylethoxy, phenoxy, sulfophenoxy, C 1 -C 4 -alkylmercapto, phenylmercapto, amino, β-C 1 -C 4 -alkanoylamino, benzolyamino, C 1 -C 4 -monoalkylamino or -dialkylamino, phenylamino, sulfophenylamine, C 1 -C 4 -alkylsulfonylamino, phenylsulfonylamino or hydroxysulfonyl; R 1 and R 2 independently are hydrogen; C 1 -C 8 -alkyl; C 1 -C 8 -alkyl interrupted by oxygen and substituted by hydroxyl, carboxyl, cyano, chlorine, bromine, phenyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkanoyloxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkanoylamino, acetyl, C 1 -C 4 -alkylaminocarbonyloxy, arylamino-carbonyloxy, C 1 -C 4 -alkoxycarbonyloxy or phenoxycarbonyloxy; allyl; methallyl; propargyl; cyclohexyl; phenyl-C 1 -C 5 -alkyl; phenyl; naphthyl; or phenyl or naphthyl substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkoxycarbonyl, carboxyl, nitro or C 1 -C 4 -alkanoylamino; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino, morpholino, piperazino, α-methylpiperazino, hexamethyleneimino or thiomorpholino-S-dioxide; and wherein the molecule contains from 1 to 4 --SO 3 H groups in at least one of the D, R, R 1 and R 2 radicals.

Claim 5

A light fast and wet fast acid azo dye containing a thiazole coupling component and having the formula: ##STR163## wherein D is phenyl or naphthyl substituted by arylazo, R is acetyl; benzoyl; C 1 -C 4 -alkyl; C 1 -C 4 alkyl substituted by chlorine, bromine, cyano, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkylmercapto, phenoxy, sulfophenoxy, phenylmercapto, amino, N-mono- or N,N-di-C 1 -C 4 -alkylamino, phenylamino, sulfophenylamino, C 1 -C 4 -alkanoylamino or sulfoethylamino; vinyl; cyclohexyl; phenyl; thienyl; thiazolyl; or phenyl, thienyl or thiazolyl substituted by fluorine, chlorine, bromine, hydroxyl, C 1 -C 4 -alkoxy, β-C 1 -C 4 -alkanoyloxyethoxy, β-cyanoethoxy, β-carboxylethoxy, β-C 1 -C 4 -alkoxycarbonylethoxy, phenoxy, sulfophenoxy, C 1 -C 4 -alkylmercapto, phenylmercapto, amino, β-C 1 -C 4 -alkanoylamino, benzolyamino, C 1 -C 4 -monoalkylamino or -dialkylamino, phenylamino, sulfophenylamine, C 1 -C 4 -alkylsulfonylamino, phenylsulfonylamino or hydroxysulfonyl; R 1 and R 2 independently are hydrogen; C 1 -C 8 -alkyl; C 1 -C 8 -alkyl interrupted by oxygen and substituted by hydroxyl, carboxyl, cyano, chlorine, bromine, phenyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkanoyloxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -alkanoylamino, acetyl, C 1 -C 4 -alkylaminocarbonyloxy, arylamino-carbonyloxy, C 1 -C 4 -alkoxycarbonyloxy or phenoxycarbonyloxy; allyl; methallyl; propargyl; cyclohexyl; phenyl-C 1 -C 5 -alkyl; phenyl; naphthyl; or phenyl or naphthyl substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkoxycarbonyl, carboxyl, nitro or C 1 -C 4 -alkanoylamino; or R 1 and R 2 together with the nitrogen atom are pyrrolidino, piperidino, morpholino, piperazino, α-methylpiperazino, hexamethyleneimino or thiomorpholino-S-dioxide; and wherein the molecule contains from 1 to 4 --SO 3 H groups in at least one of the D, R, R 1 and R 2 radicals.

Claim 6

The acid azo dye of claim 2, wherein said radical R is CH 3 , C 2 H 5 , CH 2 Cl, CH 2 CN, CH 2 OH, CH 2 --CH 2 Cl, CH 2 --CH 2 OH, CH 2 --CH 2 CN, CH 2 --COOCH 3 , CH 2 COOC 2 H 5 , CH 2 --COOH, CH 2 --NHC 2 H 4 SO 3 H, --CH 2 OCH 3 , --CH 2 OC 2 H 5 , CH 2 SCH 3 , CH 2 N(CH 3 ) 2 , C 6 H 5 OCH 2 , HO 3 SC 6 H 4 OCH 2 , C 6 H 5 , ClC 6 H 4 , BrC 6 H 4 , FC 6 H 4 , Cl 2 C 6 H 3 , CH 3 C 6 H 4 , (CH 3 ) 2 C 6 H 3 , CH 3 OC 6 H 4 , C 2 H 5 OC 6 H 4 , NCC 2 H 4 OC 6 H 4 , CH 3 OOC.C 2 H 4 OC 6 H 4 , HOOC--C 2 H 4 OC 6 H 4 , H 2 NCOC 2 H 4 OC 6 H 4 , CH 3 COOC 2 H 4 OC 6 H 4 , HOC 2 H 4 OC 6 H 4 , HOC 6 H 4 , C 6 H 5 OC 6 H 4 , HO 3 SC 6 H 4 --OC 6 H 4 , CH 3 SC 6 H 4 , C 6 H 5 SC 6 H 4 , NC--C 2 H 4 SC 6 H 4 , CH 3 CONHC 6 H 4 , C 2 H 5 CONHC 6 H 4 , H 2 N--C 6 H 4 , HOC 2 H 4 NHC 6 H 4 , (C 2 H 5 ) 2 NC 6 H 4 , CH 3 SO 2 NHC 6 H 4 , C 6 H 5 SO 2 NHC 6 H 4 , C 6 H 5 NHC 6 H 4 , CH 3 CONHC 6 H 3 SO 3 H, CH 3 OC 6 H 3 SO 3 H, ##STR164##

Claim 7

The acid azo dye of claim 2, wherein said radicals R 1 and R 2 are each hydrogen, methyl, ethyl, propyl, butyl, β-hydroxyethyl, β-methoxyethyl, γ-methoxypropyl, β-cyanoethyl, β-carbomethoxyethyl, β-carboethoxyethyl, β-acetoxyethyl, β-ethoxycarbonylethyl, γ-acetylaminopropyl, phenoxycarbonyloxyethyl, phenylaminocarbonyloxyethyl, butylaminocarbonyloxyethyl, benzyl, β-phenylethyl, phenyl, sulfophenyl, disulfophenyl, acetylaminophenyl, carboxyphenyl, cyanophenyl, chlorophenyl, sulfoethyl, ##STR165##