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US4997919A Expired / Lapsed US ⏱️ 0.0 years remaining

Azo direct dyes containing a non-reactive triazinyl moiety

Assignee: BASF Corp
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Filing: 1989-06-19
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Granted: 1991-03-05
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Expires: 2009-06-19
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Abstract

Abstract This invention relates to direct dyes for various substrates, in particular cellulosic fiber materials. The inventive dyes are high-temperature-resistant and highly suitable for the single bath, one step dyeing of polyester/cotton mixed fabrics with a disperse dye for the polyester fibers under the dyeing conditions for polyester fibers. The inventive dyes are of the formula ##STR1## in which A is a radical of the formula ##STR2## A' has the meaning of A or is a mono- or polyazo dye radical which is different from A, R and R', independently of one another, are hydrogen or C 1 -C 4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R 1 is hydroxyl, C 1 -C 4 alkoxy, halogen, C 1 -C 4 alkylthio, amino, N-mono- or N,N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C 1 -C 4 alkoxy, cyclohexylamino, phenylamino or N-C 1 -C 4 alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl moiety by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, carboxyl, sulfo or halogen, morpholino, piperidino or 3-carboxy- or 3-carboxamidopyridin-1-yl, R 2 is unsubstituted or hydroxy-substituted C 1 -C 4 alkyl, and the phenyl radical (a) is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl, carboxyl, sulfo, --NHCOR 2 or unsubstituted or sulfo-, C 1 -C 4 alkoxy-, hydroxyl- or halogen-substituted phenylazo or 1-2-naphthylazo.

Inventors

  • 👤 Rudolf Schaulin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 21:59
CPC Classifications
C; C09; C09B; C09B43/00; C09B43/12; C09B43/136; C09B43/16; D; D06; D06P; D06P3/00; D06P3/34; D06P3/52; D06P3/54

Claims Analysis

Total Claims: 14
Claim 1
Independent Claim 328 words
A compound of the formula ##STR102## in which A is a radical of the formula ##STR103## A' has the meaning of A or is a radical of the formula ##STR104## in which R 4 is hydrogen, methyl, methoxy, sulfo, chlorine, acetylamino, hydroxyacetylamino, propionylamino or carboxyl, R 5 has the meaning of 1 to 3 identical or different radicals selected from the group consisting of sulfo, methyl, methoxy, chlorine, hydroxyl, carboxyl and o- , m- or p- sulfophenylazao, R 6 is hydrogen, C 1 -C 4 - alkyl or C 1 -C 4 - alkoxy -C 1 -C 4 - alkyl, R 7 is sulfomethyl, cyano or carbamoyl, R 8 is methyl, methoxy, chlorine, sulfo or carboxyl, R 9 has the meaning of 2 to 4 identical or different substituents selected from the group consisting of hydroxyl and sulfo and R 10 has the meaning of 1 to 2 identical of different radicals selected from the group consisting of hydrogen, methyl, methoxy, sulfo, hydroxyl, amino, acetylamino and hydroxyacetylamino, R and R', independently of one another, are hydrogen or C 1 -C 4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R 1 is hydroxyl, C 1 -C 4 alkoxy, halogen, C 1 -C 4 alkylthio, amino, N-mono-or N, N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C 1 -C 4 alkoxy, cyclohexylamino, phenylamino or N-C 1 -C 4 alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl moiety by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, carboxyl, sulfo or halogen, morpholino, piperidino or 3-carboxy-3-carboxamidopyridin-1-yl, R 2 is unsubstituted or hydroxy-substituted C 1 -C 4 alkyl, and the phenyl radical (a) is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl, carboxyl, sulfo, --NHCOR 2 or unsubstituted or sulfo, C 1 -C 4 alkoxy-, hydroxyl- or halogen-substituted phenylazo or 1-2-naphthylazo.
Claim 2
Dependent Claim 328 words
A compound of the formula ##STR102## in which A is a radical of the formula ##STR103## A' has the meaning of A or is a radical of the formula ##STR104## in which R 4 is hydrogen, methyl, methoxy, sulfo, chlorine, acetylamino, hydroxyacetylamino, propionylamino or carboxyl, R 5 has the meaning of 1 to 3 identical or different radicals selected from the group consisting of sulfo, methyl, methoxy, chlorine, hydroxyl, carboxyl and o- , m- or p- sulfophenylazao, R 6 is hydrogen, C 1 -C 4 - alkyl or C 1 -C 4 - alkoxy -C 1 -C 4 - alkyl, R 7 is sulfomethyl, cyano or carbamoyl, R 8 is methyl, methoxy, chlorine, sulfo or carboxyl, R 9 has the meaning of 2 to 4 identical or different substituents selected from the group consisting of hydroxyl and sulfo and R 10 has the meaning of 1 to 2 identical of different radicals selected from the group consisting of hydrogen, methyl, methoxy, sulfo, hydroxyl, amino, acetylamino and hydroxyacetylamino, R and R', independently of one another, are hydrogen or C 1 -C 4 alkyl which is unsubstituted or substituted by chlorine, hydroxyl, cyano, carboxyl, sulfo, sulfato, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, R 1 is hydroxyl, C 1 -C 4 alkoxy, halogen, C 1 -C 4 alkylthio, amino, N-mono-or N, N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl or C 1 -C 4 alkoxy, cyclohexylamino, phenylamino or N-C 1 -C 4 alkyl-N-phenylamino which are unsubstituted or substituted in the phenyl moiety by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, carboxyl, sulfo or halogen, morpholino, piperidino or 3-carboxy-3-carboxamidopyridin-1-yl, R 2 is unsubstituted or hydroxy-substituted C 1 -C 4 alkyl, and the phenyl radical (a) is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl, carboxyl, sulfo, --NHCOR 2 or unsubstituted or sulfo, C 1 -C 4 alkoxy-, hydroxyl- or halogen-substituted phenylazo or 1-2-naphthylazo.
Claim 3
Dependent Claim 13 words
A compound according to claim 1, wherein R and R' are each hydrogen.
Claim 4
Dependent Claim 63 words
A compound according to claim 1, wherein R 1 is N-mono- or N, N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl, methoxy or ethoxy, phenylamino which is unsubstituted or substituted in the phenyl moiety by chlorine, methyl, methoxy or sulfo, N-C 1 -C 4 alkyl-N-phenylamino, C 1 -C 4 alkylthio, chlorine, morpholino or piperidino.
Claim 5
Dependent Claim 36 words
A compound according to claim 1, wherein R 1 is morpholino or an N-mono- or N, N-di-C 1 -C 4 alkylamino radical which is unsubstituted or substituted in the alkyl moiety by hydroxyl, methoxy or ethoxy.
Claim 6
Dependent Claim 14 words
A compound according to claim 4, wherein R 1 is morpholino or N, N-di-β-hydroxyethylamino.
Claim 7
Dependent Claim 22 words
A compound according to claim 1, wherein R 2 is C 1 -C 3 alkyl which is unsubstituted or substituted by hydroxyl.
Claim 8
Dependent Claim 15 words
A compound according to claim 6, wherein R 2 is a methyl or hydroxymethyl radical.
Claim 9
Dependent Claim 31 words
A compound according to claim 1, wherein the phenyl radical (a) is unsubstituted or further substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl or carboxyl.
Claim 10
Dependent Claim 254 words
A compound according to claim 1 of the formula ##STR105## in which R 1 ' is chlorine, orpholino, piperidino, C 1 -C 4 alkylthio, N-C 1 -C 4 alkyl-N-phenylamino, phenylamino which is unsubstituted or substituted by chlorine, methyl, methoxy or sulfo, N-mono-or N, N-di-substituted by chlorine, methyl, methoxy or sulfo, N-mono- or N, N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl, methoxy or ethoxy, R 2 ' is C 1 -C 3 alkyl which is unsubstituted or substituted by hydroxyl, R 3 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl or carboxyl, R" is hydrogen, methyl or ethyl and A" is a radical of the formula ##STR106## in which R 4 is hydrogen, methyl, methoxy, sulfo, chlorine, acetylamino, hydroxymethylamino, propionylamino or carboxyl, R 5 has the meaning of 1 to 3 identical or different radicals selected from the group consisting of sulfo, methyl, methoxy, chlorine, hydroxyl, carboxyl and o-, m- or p-sulfophenylazo, R 6 is hydrogen, C 1 -C 4 alkyl or c 1 -C 4 alkoxy, C 1 -C 4 alkyl, R 7 is sulfomethyl, cyano or carbamoyl, R 8 is methyl, methoxy, chlorine, sulfo or carboxyl, R 9 has the meaning of 2 to 4 identical or different substituents selected from the group consisting of hydroxyl and sulfo and R 10 has the meaning of 1 or 2 identical or different radicals selected from the group consisting of hydrogen, methyl, methoxy, sulfo, hydroxyl, amino, acetylamino and hydroxyacetylamino.
Claim 11
Dependent Claim 12 words
A compound according to claim 1, wherein A and A' are identical.
Claim 12
Dependent Claim 89 words
A compound according to claim 10 of the formula ##STR107## in which R 1 ' is chlorine, morpholino, piperidino, C 1 -C 4 alkylthio,, N-C 1 -C 4 alkyl-N-phenylamino, phenylamino which is unsubstituted or substituted by chlorine, methyl, methoxy or sulfo, N-mono- or N, N-di-C 1 -C 4 alkylamino which is unsubstituted or substituted in the alkyl moiety by hydroxyl, carboxyl, methoxy or ethoxy, R 2 ' is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halogen, hydroxyl or carboxyl and R" is hydrogen, methyl or ethyl.
Claim 13
Dependent Claim 49 words
A compound according to claim 11 of the formula (5) in which R 1 ' is morpholino, N-hydroxy-C 1 -C 2 alkylamino or N, N-dihydroxy-C 1 -C 2 alkylamino, R 2 ' is methyl, ethyl or hydroxymethyl, R" is hydrogen and R 3 is hydrogen, methyl, methoxy or chlorine.
Claim 14
Dependent Claim 36 words
A compound according to claim 11 of the formula ##STR108## in which R 1 " is N, N-di-β-hydroxyethylamino or morpholino, R 2 " is methyl or hydroxymethyl and R 3 ' is hydrogen, methyl or methoxy.

References Cited (Backward Citations)

US3945990A Cited
GB1525280A Cited
GB1544425A Cited
GB2036780A Cited
US4542208A Cited
US4605442A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-03-04 1994-09-03 1995-03-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-03-04 1998-09-03 1999-03-05 $3760.00 Window Closed / Lapsed
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