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Azo compounds having a 5-substituted-4-chlorothiazolyl-2-diazo component radical
| Details |
Inventors: Egli, Robert;
Assignee: Sandoz Ltd. (Basel, CH)
Primary Examiner: Higel; Floyd D.
Assistant Examiner:
Attorney, Agent or Firm: Sharkin; Gerald D., Vila; Richard E., Kassenoff; Melvyn M.
Compounds of the formula ##STR1## in which K is the radical of a coupling component of the aniline, .alpha.-naphthylamine, pyrazolone, aminopyrazole, indole, tetrahydroquinoline, thiazole, phenol, naphthol, pyridine or pyridone series. R is --CHO, --CH.dbd.C(CN)--R.sub.1, --CH.dbd.CH--R.sub.2, --CH.dbd.C(NO.sub.2)--R.sub.3, --CH.dbd.NOH or --CN, wherein R.sub.1 is (C.sub.1-10 alkoxycarbonyl; (C.sub.1-10 alkoxy)carbonyl monosubstituted by chloro, bromo, cyano, hydroxy, C.sub.1-2 alkoxy, (C.sub.1-2 alkyl)carbonyloxy or (C.sub.1-2 alkoxy)carbonyl; (C.sub.1-10 alkoxy)carbonyl disubstituted by hydroxy and by chloro or bromo; (C.sub.3-8 alkenyl)oxycarbonyl; (C.sub.3-8 chloroalkenyl)oxycarbonyl; (C.sub.3-8 bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl; chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C.sub.1-4 alkylsulfonyl; phenylsulfonyl; tolylsulfonyl; carbamoyl; (C.sub.1-2 alkyl)carbamoyl; di(C.sub.1-2 alkyl)carbamoyl; phenylcarbamoyl; aminothiocarbonyl; benzimidazolyl-2; cyano; acetyl; phenyl; benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and R.sub.2 is phenyl; benzoyl or phenyl or benzoyl substituted by 1, 2 or 3 substituents each of which is independently chloro, bromo or nitro, with the proviso that the maximum number of nitro groups is two, and R.sub.3 is hydrogen, methyl or ethyl, and m is 0 or 1, useful as disperse dyes for dyeing and printing textile substrates comprising or consisting of synthetic or semi-synthetic, hydrophobic, high molecular weight, organic materials such as linear aromatic polyesters, cellulose 21/2 acetate, cellulose triacetate and synthetic polyamides, with those wherein R is formyl also being useful for dyeing wool. |
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DETAILED DESCRIPTION What is claimed is: 1.
A compound of the formula ##STR29## wherein K is the radical of a coupling component, said coupling component being 1-phenyl-3-methyl-5-aminopyrazole, 1-phenyl-3-methylpyrazolone-5,3-methylpyrazolone-5,1-(2'-hydroxyethyl)-3-m ethylpyrazolone-5,1-n-butyl-3-cyano-4-methyl-6-hydroxypyridone-2,1-methyl-2 -phenylindole, 2-hydroxydiphenyl, p-cresol, 2-hydroxynaphthalene-3-carboxylic acid ethyl ester, 2-diethylamino-b 4-phenyl-1,3-thiazole, 2-benzylamino-3-cyano-4-methyl-6-(2'-hydroxyethyl)pyridine, 2,6-di-(n-butylamino)-3-cyano-4-methylpyridine, 2,6-di(3'-methoxypropylamino)-3-cyano-4-methylpyridine, 2-benzylamino-3-cyano-4,6-di-(methylamino)pyridine, 2,4,6-tri-(3'-methoxypropylamino)-3-cyanopyridine, 1-(N-cyanoethyl)naphthylamine or N-(3'-methoxypropylamino)-4-hydroxynaphthalimide, ##STR30## wherein R.
sub.
5 is hydrogen; C.
sub.
1-2 alkyl; C.
sub.
1-2 alkoxy; cyano; formamido; (C.
sub.
1-4 alkyl)carbonylamino; (C.
sub.
1-4 alkyl)carbonylamino the alkyl moiety of which is monosubstituted by hydroxy, chloro, bromo, C.
sub.
1-4 alkoxy, phenyl, phenoxy, benzloxy or (C.
sub.
1-2 alkoxy)carbonyl; benzamido; acryloylamino; allylcarbonylamino; aminocarbonylamino; (C.
sub.
1-4 alkyl)aminocarbonylamino; (C.
sub.
1-4 alkoxy)carbonylamino; (C.
sub.
1-4 alkoxy)carbonylamino the alkoxy moiety of which is monosubstituted by C.
sub.
1-2 alkoxy or phenyl; C.
sub.
1-2 alkylsulfonylamino; phenylsulfonylamino; di-(C.
sub.
1-2 alkyl)aminosulfonylamino; chloro or bromo, R.
sub.
6 is hydrogen, chloro, bromo, C.
sub.
1-2 alkyl, C.
sub.
1-2 alkoxy or (C.
sub.
1-2 alkoxy)ethoxy, with the proviso that not more than one of R.
sub.
5 and R.
sub.
6 is chloro or bromo, R.
sub.
7 is hydrogen; C.
sub.
1-8 alkyl; C.
sub.
1-4 alkyl substituted by 1 or 2 substituents each of which is independently chloro, bromo, hydroxy, thiocyano, cyano, (C.
sub.
1-4 alkyl)carbonyl, (C.
sub.
1-4 alkoxy)carbonyl, formyloxy, (C.
sub.
1-10 alkyl)carbonyloxy, cyclohexyl, (C.
sub.
1-3 chloroalkyl)carbonyloxy, (C.
sub.
1-3 bromoalkyl)carbonyloxy, (C.
sub.
1-10 alkoxy)carbonyloxy, (C
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