Claims
- 1. A basic azo dyestuff, free of acid groups conferring solubility in water, of the formula ##STR293## wherein Y is --CN or --CONH.sub.2,
- two of Z.sub.1, Z.sub.2 and Z.sub.3 represent -NR'R" and the
- third represents -NR'R", -OR'" or -SR'", where R', R" and R'" independently represent hydrogen,
- alkyl of up to 12 carbon atoms, which is unsubstituted or substituted by: hydroxy, carboxy, carbalkoxy of 2 to 6 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, acyloxy or acylamino wherein acyl is alkanoyl of up to 5 carbon atoms, alkylcarbamyl of up to 5 carbon atoms, alkoxycarbonyl of up to 5 carbon atoms, phenylcarbamyl, phenoxycarbonyl, benzoyl, phenoxyacetyl, chloracetyl or phenylacetyl; or phenyl which is unsubstituted or substituted by halo, lower alkyl, lower alkoxy, .beta.-hydroxyethyl or lower carboalkoxy;
- phenyl which is unsubstituted or substituted by chloro, bromo, fluoro, alkyl of 1 to 6 carbon atoms which is unsubstituted or substituted by bromo, chloro, lower alkoxy, cyano or lower alkoxycarbonyl; lower alkoxycarbonyl, trifluoromethyl, acetyl, aminocarbonyloxy, aminosulfonyl, lower alkylaminosulfonyl, di(lower alkyl) aminosulfonyl, methylsulfonyl, ethylsulfonyl, methylthio, ethylthio or phenylthio; C.sub.5 -C.sub.9 cycloalkyl; and
- R' and R", taken together with the nitrogen atom to which they are linked, additionally represent piperidinyl, pyrollidinyl, morpholino, piperazinyl, methylpiperazinyl, acetylpiperazinyl or 3-picolyl;
- D is phenyl;
- phenyl substituted by chloro, bromo, fluoro, hydroxy, cyano, thiocyano, nitro, lower alkyl, trifluoromethyl, lower alkoxy, lower alkylmercapto, formyl, loweralkylcarbonyl, benzoyl, methylbenzoyl, lower alkoxycarbonyl, lower alkoxycarbonyloxy, benzyloxycarbonyloxy, cyclohexylcarbonyl, phenoxycarbonyl, benzoyloxy, lower alkylcarbonylamino, benzoylamino, loweralkylsulphonyl, chloroethylsulphonyl, hydroxyethylsulphonyl, aminosulphonyl, N-(lower alkyl) aminosulphonyl, N,N-(diloweralkyl) aminosulphonyl, di(.beta.-hydroxyethyl) aminosulphonyl, phenylaminosulphonyl, (chloro-or methoxy-) phenylaminosulphonyl, benzylaminosulphonyl, N-piperidylsulphonyl, N-morpholinosulphonyl, lower alkylsulphonyloxy, cyclohexylsulphonyloxy, chloromethylsulphonyloxy, cyanoethylsulphonyloxy, phenylsulphonyloxy, aminosulphonyloxy, (chloro- or methoxy-) phenylsulphonyloxy, N-morpholinosulphonyloxy, ethyleneiminosulphonyloxy, lower monoalkylaminosulphonyloxy, phenylaminosulphonyloxy, N-phenyl-N(lower alkyl) aminosulphonyloxy, N-(methoxy- or chloro-) phenylaminosulphonyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, phenoxy or acetylphenyl; phenylazophenyl;
- phenylazophenyl substituted by chloro, bromo, hydroxy, cyano, nitro, lower alkyl, trifluoromethyl, lower alkoxy or phenoxy; napthyl;
- napthyl substituted by methoxy, ethoxy, phenylazo or dimethylaminosulphonyl; or
- D is a nitrogen heterocyclic group selected from thiazolyl or thiazolyl substituted by chloro, bromo, cyano, thiocyano, lower alkyl, lower alkoxy, lower alkylmercapto, phenyl, benzyl, phenethyl, lower alkoxycarbonyl, trifluoromethyl, lower alkylcarbonyl or lower alkylsulphonyl;
- benzythiazolyl or benzthiazolyl substituted by chloro, bromo, cyano, thiocyano, nitro, lower alkyl, lower alkoxy, benzyl, phenylethyl, lower alkylsulphonyl, phenyl, lower alkylmercapto, lower alkoxycarbonyl, lower alkylcarbonyl, trifluoromethyl, cyanoethylsulphonyl, aminosulphonyl, lower alkylaminosulphonyl, di(lower alkyl) aminosulphonyl;
- pyrazolyl or pyrazolyl substituted by cyano, lower alkyl, lower alkoxy, lower alkoxycarbonyl or phenyl; thiadizolyl or thiadiazolyl substituted by lower alkoxy, lower alkyl, phenyl, lower alkylsulphonyl or lower alkylmercapto;
- imidazolyl or imidazolyl substituted by nitro or lower alkyl;
- isothiazolyl or isothiazolyl substituted by lower alkyl, nitro, lower alkylsulphonyl, lower alkoxycarbonyl, cyano or phenyl;
- benzisothiazolyl or benzisothiazolyl substituted by lower alkyl, nitro or halo; benzimidazolyl or benzimidazolyl substituted by lower alkyl, nitro or halo;
- napthiazolyl or napthiazolyl substituted by lower alkyl, nitro or halo;
- quinolinyl or quinolyl substituted by lower alkyl, nitro or halo;
- benzoxazolyl or benzoxazolyl substituted by lower alkyl, nitro or halo;
- pyridinyl or pyridinyl substituted by lower alkyl, nitro or halo;
- indazolyl or indazolyl substituted by lower alkyl, nitro or halo;
- selenazolyl or selenazolyl substituted by lower alkyl, nitro or halo;
- oxazolyl or oxazolyl substituted by lower alkyl, nitro or halo;
- oxadiazolyl or oxadiazolyl substituted by lower alkyl, nitro or halo; and
- triazolyl or triazolyl substituted by lower alkyl, nitro or halo; or
- D is thienyl or thienyl substituted by nitro, lower alkyl, lower alkylsulphonyl, lower alkoxycarbonyl or acetyl;
- with the proviso that either
- a. one of Z.sub.1, Z.sub.2, Z.sub.3 or D is further substituted either by a direct bond or via an alkylene, alkyleneoxy, alkylenecarbonyl, carbonyloxy, carbonylamino, alkylenecarbonyloxy, alkylenecarbonylamino, alkylenesulphonylamino or alkylenesulphonyl group by ##STR294## wherein R.sub.1 '" and R.sub.2 '" independently represent lower alkyl, benzyl, phenethyl, .beta.-hydroxyethyl, .beta.-carbethoxyethyl or cyclohexyl,
- R.sub.3 '" is lower alkyl, benzyl, cyclohexyl, lower alkoxy or --NH.sub.2
- and two of R.sub.1 '", R.sub.2 '" and R.sub.3 '" can further represent, together with the nitrogen to which they are attached, piperidino, methylpiperdino, pyrrolidino, morpholino, piperazinyl or imidazolyl,
- X is an anion and m is 1 or 2; or by ##STR295## wherein R.sub.4 '" is alkyl of 1-4 carbon atoms, cyclohexyl or benzyl,
- X is an anion and m is 1 or 2; or
- b. when D is said nitrogen heterocyclic group, D is in the form of its N-(lower alkyl or benzyl) quaternary ammonium salt thereof.
- 2. A basic azo dyestuff according to claim 1 of the formula ##STR296##
- 3. A basic azo dyestuff according to claim 1, wherein Y is --CN.
- 4. A basic azo dyestuff according to claim 2, wherein D is said nitrogen heterocyclic group.
- 5. A basic azo dyestuff according to claim 2, wherein R' and R" are hydrogen.
- 6. A basic azo dyestuff according to claim 2, which is substituted by ##STR297##
- 7. A basic azo dyestuff according to claim 2, which is substituted by ##STR298##
- 8. A basic azo dyestuff according to claim 6, wherein R.sub.1 '", R.sub.2 '" and R.sub.3 '" are lower alkyl.
- 9. A basic azo dyestuff according to claim 7, wherein R.sub.4 '" is lower alkyl.
- 10. A basic azo dyestuff according to claim 2, wherein D is said phenyl substituted phenyl, phenylazophenyl or substituted phenylazophenyl.
- 11. A basic azo dyestuff, free from acid groups conferring water-solubility of the formula ##STR299## wherein R.sub.1 ' is cycloalkyl of 5 to 9 carbon atoms or alkyl of 1 to 6 carbon atoms which is unsubstituted or substituted by: hydroxy, carboxy, cyano, carbalkoxy of 2 to 6 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, phenyl or phenyl substituted by halo, lower alkyl, lower alkoxy, .beta.-hydroxyethyl or lower carbalkoxy;
- alkylcarbamyl of up to 5 carbon atoms, alkylcarbamyl of up to 5 carbon atoms, alkoxycarbonyl of up to 5 carbon atoms, phenylcarbamyl, phenoxycarbonyl, benzoyl, phenoxyacetyl, chloroacetyl or phenylacetyl;
- Y is --CN or --CONH.sub.2 ,
- z.sub.2 is ##STR300## or OR'" or --SR'", wherein
- R', r" and R'" represent
- hydrogen,
- alkyl of up to 12 carbon atoms, which is unsubstituted or substituted by: hydroxy, carboxy, carbalkoxy of 2 to 6 carbon atoms, alkoxy of 1 to 8 carbon atoms, phenoxy, acyloxy or acylamino wherein acyl is alkanoyl of up to 5 carbon atoms, alkylcarbamyl of up to 5 carbon atoms, alkoxycarbonyl of up to 5 carbon atoms, phenylcarbamyl, phenoxycarbonyl, benzoyl, phenoxyacetyl, chloracetyl or phenylacetyl; or phenyl which is unsubstituted or substituted by halo, lower alkyl, lower alkoxy, .beta.-hydroxyethyl or lower carboalkoxy;
- phenyl which is unsubstituted or substituted by chloro, bromo, fluoro, alkyl of 1 to 6 carbon atoms which is unsubstituted or substituted by bromo, chloro, lower alkoxy, cyano or lower alkoxycarbonyl; lower alkoxycarbonyl, trifluoromethyl, acetyl, aminocarbonyloxy, aminosulfonyl, lower alkylaminosulfonyl, di(lower alkyl) aminosulfonyl, methylsulfonyl, ethylsulfonyl, methylthio, ethylthio or phenylthio;
- C.sub.5 -c.sub.9 cycloalkyl; and
- R' and R", taken together with the nitrogen atom to which they are linked, additionally represent piperindinyl, pyrollidinyl, morpholino, piperazinyl, methylpiperazinyl, acetylpiperazinyl or 3-picolyl;
- D is phenyl;
- phenyl substituted by chloro, bromo, fluoro, hydroxy, cyano, thiocyano, nitro, lower alkyl, trifluoromethyl, lower alkoxy, lower alkylmercapto, formyl, lower-alkylcarbonyl, benzoyl, methylbenzoyl, lower alkoxycarbonyl, lower alkoxycarbonyloxy, benzyloxycarbonyloxy, cyclohexylcarbonyl, phenoxycarbonyl, benzoyloxy, lower alkylcarbonylamino, benzoylamino, loweralkylsulphonyl, chloroethylsulphonyl, hydroxyethylsulphonyl, aminosulphonyl, N-(lower alkyl) aminosulphonyl, N,N-(diloweralkyl) aminosulphonyl, di(.beta.-hydroxyethyl) aminosulphonyl, phenylaminosulphonyl, (chloro-or methoxy-) phenylaminosulphonyl, benzylaminosulphonyl, N-piperidylsulphonyl, N-morpholinosulphonyl, lower alkylsulphonyloxy, cyclohexylsulphonyloxy, chloromethylsulphonyloxy, cyanoethylsulphonyloxy, phenylsulphonyloxy, aminosulphonyloxy, (chloro-or methoxy-) phenylsulphonyloxy, N-morpholinosulphonyloxy, ethyleneiminosulphonyloxy, lower monoalkylaminosulphonyloxy, phenylaminosulphonyloxy, N-phenyl-N(lower alkyl) aminosulphonyloxy, N- (methoxy- or chloro-) phenylaminosulphonyloxy, phenylamino, nitrophenylamino, dinitrophenylamino, phenyl, phenoxy or acetylphenyl; phenylazophenyl;
- phenylazophenyl substituted by chloro, bromo, hydroxy, cyano, nitro, lower alkyl, trifluoromethyl, lower alkoxy or phenoxy; napthyl;
- napthyl substituted by methoxy, ethoxy, phenylazo or dimethylaminosulphonyl; or
- D is a nitrogen heterocyclic group selected from thiazolyl or thiazolyl substituted by chloro, bromo, cyano, thiocyano, lower alkyl, lower alkoxy, lower alkylmercapto, phenyl, benzyl, phenethyl, lower alkoxycarbonyl, trifluoromethyl, lower alkylcarbonyl or lower alkylsulphonyl;
- benzythiazolyl or benzthiazolyl substituted by chloro, bromo, cyano, thiocyano, nitro, lower alkyl, lower alkoxy, benzyl, phenylethyl, lower alkylsulphonyl, phenyl, lower alkylmercapto, lower alkoxycarbonyl, lower alkylcarbonyl, trifluoromethyl, cyanoethylsulphonyl, aminosulphonyl, lower alkylaminosulphonyl, di(lower alkyl) aminosulphonyl; pyrazolyl or pyrazolyl substituted by cyano, lower alkyl, lower alkoxy, lower alkoxycarbonyl or phenyl; thiadiazolyl or thiadiazolyl substituted by lower alkoxy, lower alkyl, phenyl, lower alkylsulphonyl or lower alkylmercapto;
- imidazolyl or imidazolyl substituted by nitro or lower alkyl;
- isothiazolyl or isothiazolyl substituted by lower alkyl, nitro, lower alkylsulphonyl, lower alkoxycarbonyl, cyano or phenyl;
- benzisothiazolyl or benzisothiazolyl substituted by lower alkyl, nitro or halo;
- benzimidazolyl or benzimidazolyl substituted by lower alkyl, nitro or halo;
- napthiazolyl or napthiazolyl substituted by lower alkyl, nitro or halo;
- quinolinyl or quinolyl substituted by lower alkyl, nitro or halo;
- benzoxazolyl or benzoxazolyl substituted by lower alkyl, nitro or halo;
- pyridinyl or pyridinyl substituted by lower alkyl, nitro or halo;
- indazolyl or indazolyl substituted by lower alkyl, nitro or halo;
- selenazolyl or selenazolyl substituted by lower alkyl, nitro or halo;
- oxazolyl or oxazolyl substituted by lower alkyl, nitro or halo;
- oxadiazolyl or oxadiazolyl substituted by lower alkyl, nitro or halo; and
- triazolyl or triazolyl substituted by lower alkyl, nitro or halo; or
- D is thienyl or thienyl substituted by nitro, lower alkyl, lower alkylsulphonyl, lower alkoxycarbonyl or acetyl; with the proviso that either
- a. one of Z.sub.2 or D is further substituted either by a direct bond or via an alkylene, alkyleneoxy, alkylenecarbonyl, carbonyloxy, carbonylamino, alkylenecarbonyloxy, alkylenecarbonylamino, alkylenesulphonylamino or alkylenesulphonyl group by ##STR301## wherein R.sub.1 '" and R.sub.2 '" independently represent lower alkyl, benzyl, phenethyl, .beta.-hydroxyethyl, .beta.-carbethoxyethyl, or cyclohexyl,
- R.sub.3 '" is lower alkyl, benzyl, cyclohexyl, lower alkoxy or --NH.sub.2
- and two of R.sub.1 '", R.sub.2 '" and R.sub.3 '" can further represent, together with the nitrogen to which they are attached, methylpiperidino, pyrrolidino, piperidino, morpholino, piperazinyl or imidazolyl,
- X is an anion and m is 1 or 2; or by ##STR302## wherein R.sub.4 '" is alkyl of 1-4 carbon atoms, cyclohexyl or benzyl,
- X is an anion and m is 1 or 2; or
- b. when D is said nitrogen heterocyclic group, D is in the form of its N-(lower alkyl or benzyl) quaternary ammonium salt thereof.
- 12. A basic azo dyestuff according to claim 11, wherein R.sub.1 ' is alkyl of 1 to 6 carbon atoms, cyclohexyl, benzyl or phenethyl.
- 13. A basic azo dyestuff according to claim 11, wherein Z.sub.2 is --NR'R".
- 14. A basic azo dyestuff according to claim 11, wherein Z.sub.2 is said --OR'" group and R'" is said phenyl or substituted phenyl.
- 15. A basic azo dyestuff according to claim 11, wherein Y is --CN.
- 16. A basic azo dyestuff according to claim 11, wherein D is said phenyl, substituted phenyl, phenylazophenyl or substituted phenylazophenyl.
- 17. A basic azo dyestuff according to claim 11 which is substituted by ##STR303##
- 18. A basic azo dyestuff according to claim 11 which is substituted by ##STR304##
- 19. A basic azo dyestuff according to claim 17, wherein R.sub.1 '", R.sub.2 '" and R.sub.3 '" are alkyl of 1-4 carbon atoms.
- 20. A basic azo dyestuff according to claim 18, wherein R.sub.4 '" is alkyl of 1-4 carbon atoms.
- 21. A basic azo dyestuff according to claim 11, of the formula ##STR305## wherein Z is --NR'R".
- 22. A basic azo dyestuff according to claim 11, wherein D is said nitrogen heterocyclic group.
- 23. An azo dyestuff according to claim 1 of the formula ##STR306##
- 24. An azo dyestuff according to claim 1 of the formula ##STR307##
- 25. An azo dyestuff according to claim 11 of the formula ##STR308##
Parent Case Info
This is a continuation of application Ser. No. 480,457, filed June 18, 1974, now abandoned, which in turn is a continuation-in-part of application Ser. No. 316,803, filed Dec. 20, 1972 and now abandoned.
US Referenced Citations (12)
Continuations (1)
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Date |
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Parent |
480457 |
Jun 1974 |
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Continuation in Parts (1)
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316803 |
Dec 1972 |
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