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US 4,065,447 AGranted
Azo compounds having a 3-arylthio- or aliphaticthio-4-cyano- or alkoxycarbonyl-pyrazolyl-5 diazo component radical
AssigneeSandoz Ltd.
InventorArmand Jotterand
Life of this patent
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Abstract
Disclosed are azo dyes of the formula ##STR1## wherein R.sub.1 is an aliphatic or aryl group, R.sub.2 is cyano, alkoxycarbonyl or substituted alkoxycarbonyl, R.sub.3 is an aliphatic or aryl group, and K is a coupling component radical, The synthesis thereof and the use thereof for the dyeing and printing of textile and non-textile substrates. The disclosed disperse dyes are useful for dyeing and printing synthetic and semi-synthetic, hydrophobic, high molecular weight materials such as linear aromatic polyesters, polyamides, cellulose 21/2 acetate and cellulose triacetate. The obtained dyeings have satisfactory fastness properties, particularly fastness to light, thermofixation, sublimation and pleating.
Claims14
A monoazo dye of the formula ##STR35## wherein each of R.sub.1 and R.sub.3 is independently C.sub.2-4 alkenyl;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by hydroxy, cyano, C.sub.1-4 alkoxy, phenyl, phenoxy, chloro or bromo;
- phenyl or substituted phenyl having 1 to 3 substituents each of which is independently chloro, bromo, methyl, methoxy, ethoxy, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl or di-(C.sub.1-4 alkyl)sulfamoyl, with the proviso that the maximum number of substituents selected from the group consisting of methoxy, ethoxy, cyano and nitro is two and the maximum number of substituents selected from the group consisting of methoxycarbonyl, ethoxycarbonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl and di-(C.sub.1-4 alkyl)sulfamoyl is one,
- R.sub.2 is cyano or (C.sub.1-4 alkoxy)carbonyl, and
- K is a coupling component radical of the N-alkyl-aminobenzene, N,N-dialkylaminobenzene, .alpha.-N-alkyl-aminonaphthalene, .alpha.-N,N-dialkylaminonaphthalene, pyrazolone, 5-aminopyrazole or 3-cyano-4-alkyl-6-hydroxypyridone-2 series.
2 more elements
A compound of the formula ##STR36## wherein each of R.sub.1 and R.sub.3 is independently C.sub.2-4 alkenyl;
- C.sub.1-4 alkyl;
- C.sub.1-4 alkyl monosubstituted by hydroxy, cyano, C.sub.1-4 alkoxy, phenyl, phenoxy, chloro or bromo;
- phenyl or substituted phenyl having 1 to 3 substituents each of which is independently chloro, bromo, methyl, methoxy, ethoxy, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl or di-(C.sub.1-4 alkyl)sulfamoyl, with the proviso that the maximum number of substituents selected from the group consisting of methoxy, ethoxy, cyano and nitro is two and the maximum number of substituents selected from the group consisting of methoxycarbonyl, ethoxycarbonyl, sulfamoyl, C.sub.1-4 alkylsulfamoyl and di-(C.sub.1-4 alkyl)sulfamoyl is one,
- R.sub.2 is cyano or (C.sub.1-4 alkoxy)carbonyl, and
- K is 4-N-.beta.-(C.sub.1-4 alkoxy)carbonylethylaminonaphthyl-1, 1-C.sub.1-4 alkyl-3-cyano-4-methyl-6-hydroxypyridon-2-yl-5, 1-phenyl-3-methylpyrazolon-5-yl-4, 1-phenyl-3-methyl-5-aminopyrazolyl-4 or ##STR37## wherein R.sub.4 is hydrogen;
- chloro;
- bromo;
- cyano;
- C.sub.1-2 alkyl;
- formamido;
- (C.sub.1-4 alkyl)carbonylamino;
- (C.sub.1-4 alkyl)carbonylamino the C.sub.1-4 alkyl radical of which is monosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, phenyl or phenoxy;
- (C.sub.1-4 alkoxy)carbonylamino;
- (C.sub.1-4 alkoxy)carbonylamino the C.sub.1-4 alkoxy radical of which is monosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, phenyl or phenoxy;
- .beta.-(C.sub.1-4 alkoxy)ethoxycarbonylamino;
- .beta.-(C.sub.1-4 alkoxy)ethoxycarbonylamino the C.sub.1-4 alkoxy moiety of which is monosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, phenyl or phenoxy;
- C.sub.1-4 alkylsulfonylamino or C.sub.1-4 alkylsulfonylamino the C.sub.1-4 alkyl radical of which is nonosubstituted by chloro, bromo, cyano, C.sub.1-4 alkoxy, phenyl or phenoxy,
- R.sub.5 is hydrogen or C.sub.1-4 alkoxy,
- R.sub.6 is C.sub.2-4 alkenyl;
- 4-nitrophenyl;
- C.sub.1-4 -alkyl or substituted C.sub.1-4 alkyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, hydroxy, C.sub.1-4 alkoxy, (C.sub.1-4 alkoxy)carbonyl, .beta.-(C.sub.1-4 alkoxy)ethoxycarbonyl, (C.sub.1-4 alkoxy)carbonyloxy or (C.sub.1-4 alkyl)carbonyloxy, with the proviso that when R.sub.6 is disubstituted C.sub.1-4 alkyl, at least one of the substituents is hydroxy,
- R.sub.7 is hydrogen;
- phenyl(C.sub.1-4 alkyl);
- C.sub.2-4 -alkenyl;
- 4-nitrophenyl;
- C.sub.1-4 alkyl;
- substituted C.sub.1-4 alkyl having 1 or 2 substituents each of which is independently chloro, bromo, cyano, hydroxy, C.sub.1-4 -alkoxy, (C.sub.1-4 alkoxy)carbonyl, .beta.-(C.sub.1-4 -alkoxy)ethoxycarbonyl, (C.sub.1-4 alkoxy)carbonyloxy or (C.sub.1-4 alkyl)carbonyloxy, with the proviso that when R.sub.7 is disubstituted C.sub.1-4 alkyl, at least one of the substituents is hydroxy;
- ##STR38## with the proviso that R.sub.6 and R.sub.7 are not simultaneously 4-nitrophenyl or t-butyl, or
- R.sub.6 and R.sub.7 taken together are --CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 --,
- with the proviso that any alkyl or alkoxy radical substituted by hydroxy, alkoxy, alkoxycarbonyloxy, phenoxy or alkylcarbonyloxy has more than one carbon atom and is not substituted in its .alpha.-position.
27 more elements
Dependencies are inferred from the claim text.