US4207233A
Expired / Lapsed
US
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Azo dyes containing a thiazole component
Assignee: BASF SE
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Filing: 1977-08-24
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Granted: 1980-06-10
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Expires: 1997-08-24
Abstract
Abstract Azo dyes of the formula ##STR1## where A is a radical of a diazo component, B is a radical of a coupling component and R is hydrogen, halogen, a substituted or unsubstituted hydrocarbon radical, substituted or unsubstituted alkoxy or aroxy, or substituted amino. The dyes are eminently suitable for dyeing polyester and particularly for cellulose and blends of cellulose with polyesters.
Inventors
- 👤 Guenther Seybold
- 👤 Heinz Eilingsfeld
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 06:13
CPC Classifications
C; C09; C09B; C09B31/00; C09B31/16; C09B31/02; C09B31/025; C09B62/00; C09B62/02; C09B62/04; C09B62/08; C09B62/09
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
514 words
A dye of the formula ##STR81## where T 1 is phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, alkoxy of 1 to 4 carbon atoms, phenylazo, cyano, nitro, methylsulfonyl, ethylsulfonyl, dialkylcarbamoyl where alkyl is of 1 to 4 carbon atoms, dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms, alkoxycarbonyl where alkoxy is of 1 to 8 carbon atoms, alkylmercapto where alkyl is of 1 to 4 carbon atoms or phenylmercapto; thiazolyl; thiazolyl substituted by alkyl of 1 to 4 carbon atoms, phenyl or cyano; benzthiazolyl; benzthiazolyl substituted by chlorine, bromine, methyl, ethyl, alkoxy of 1 to 4 carbon atoms or methylsulfonyl; thienyl; or thienyl substituted by alkyl of 1 to 4 carbon atoms, cyano, nitro, phenyl or alkoxycarbonyl where alkoxy is of 1 to 8 carbon atoms; T 2 is hydrogen; alkyl of 1 to 4 carbon atoms; alkyl of 2 to 4 carbon atoms substituted by chlorine, bromine, hydroxyl, alkoxy of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms, phenoxy, phenylmercapto, cyano, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, monoalkyl- carbamoyl where alkyl is of 1 to 4 carbon atoms, dialkyl-carbamoyl where alkyl is of 1 to 4 carbon atoms, monoalkyl-sulfamoyl where alkyl is of 1 to 4 carbon atoms or dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms; cyclohexyl; benzyl; phenylethyl; phenyl; or phenyl substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, phenyl, hydroxyl, alkoxy of 1 to 4 carbon atoms, dialkylamino where alkyl is of 1 to 4 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms or phenylmercapto, and T 3 is a radical of the formula ##STR82## where B 1 is allyl, alkyl of 1 to 4 carbon atoms; alkyl of 2 to 4 carbon atoms which is substituted by hydroxyl, chlorine, bromine, cyano, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, acetyl, alkanoyloxy of 1 to 4 carbon atoms, alkylaminocarbonyloxy where alkyl is of 1 to 4 carbon atoms or phenylaminocarbonyloxy; cyclohexyl; benzyl; phenylethyl; phenyl; and methoxyphenyl; B 2 is allyl; alkyl of 1 to 4 carbon atoms; or alkyl of 2 to 4 carbon atoms which is substituted by hydroxyl, chlorine, bromine, cyano, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, acetyl, alkanoyloxy of 1 to 4 carbon atoms, alkylaminocarbonyloxy where alkyl is of 1 to 4 carbon atoms or phenylaminocarbonyloxy; B 1 and B 2 together with the nitrogen and pyrrolidino, piperidino or morpholino, B 3 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; B 4 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, monoalkylsulfamoyl where alkyl is of 1 to 4 carbon atoms, or dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms; B 5 is methyl of phenyl and B 6 is hydrogen or methyl.
Claim 2
Dependent Claim
514 words
A dye of the formula ##STR81## where T 1 is phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, ethyl, alkoxy of 1 to 4 carbon atoms, phenylazo, cyano, nitro, methylsulfonyl, ethylsulfonyl, dialkylcarbamoyl where alkyl is of 1 to 4 carbon atoms, dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms, alkoxycarbonyl where alkoxy is of 1 to 8 carbon atoms, alkylmercapto where alkyl is of 1 to 4 carbon atoms or phenylmercapto; thiazolyl; thiazolyl substituted by alkyl of 1 to 4 carbon atoms, phenyl or cyano; benzthiazolyl; benzthiazolyl substituted by chlorine, bromine, methyl, ethyl, alkoxy of 1 to 4 carbon atoms or methylsulfonyl; thienyl; or thienyl substituted by alkyl of 1 to 4 carbon atoms, cyano, nitro, phenyl or alkoxycarbonyl where alkoxy is of 1 to 8 carbon atoms; T 2 is hydrogen; alkyl of 1 to 4 carbon atoms; alkyl of 2 to 4 carbon atoms substituted by chlorine, bromine, hydroxyl, alkoxy of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms, phenoxy, phenylmercapto, cyano, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, monoalkyl- carbamoyl where alkyl is of 1 to 4 carbon atoms, dialkyl-carbamoyl where alkyl is of 1 to 4 carbon atoms, monoalkyl-sulfamoyl where alkyl is of 1 to 4 carbon atoms or dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms; cyclohexyl; benzyl; phenylethyl; phenyl; or phenyl substituted by chlorine, bromine, alkyl of 1 to 4 carbon atoms, phenyl, hydroxyl, alkoxy of 1 to 4 carbon atoms, dialkylamino where alkyl is of 1 to 4 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms or phenylmercapto, and T 3 is a radical of the formula ##STR82## where B 1 is allyl, alkyl of 1 to 4 carbon atoms; alkyl of 2 to 4 carbon atoms which is substituted by hydroxyl, chlorine, bromine, cyano, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, acetyl, alkanoyloxy of 1 to 4 carbon atoms, alkylaminocarbonyloxy where alkyl is of 1 to 4 carbon atoms or phenylaminocarbonyloxy; cyclohexyl; benzyl; phenylethyl; phenyl; and methoxyphenyl; B 2 is allyl; alkyl of 1 to 4 carbon atoms; or alkyl of 2 to 4 carbon atoms which is substituted by hydroxyl, chlorine, bromine, cyano, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, acetyl, alkanoyloxy of 1 to 4 carbon atoms, alkylaminocarbonyloxy where alkyl is of 1 to 4 carbon atoms or phenylaminocarbonyloxy; B 1 and B 2 together with the nitrogen and pyrrolidino, piperidino or morpholino, B 3 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; B 4 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkanoylamino of 1 to 4 carbon atoms, monoalkylsulfamoyl where alkyl is of 1 to 4 carbon atoms, or dialkylsulfamoyl where alkyl is of 1 to 4 carbon atoms; B 5 is methyl of phenyl and B 6 is hydrogen or methyl.
Claim 3
Dependent Claim
21 words
A dye as set forth in claim 1, where T 1 is phenyl or phenyl substituted as specified in claim 1.
Claim 4
Dependent Claim
24 words
A dye as set forth in claim 1, where T 1 is phenyl or phenyl substituted by chlorine, bromine, methyl, methoxy, ethoxy or phenylazo.
Claim 5
Dependent Claim
37 words
A dye as set forth in claim 1, where T 2 is hydrogen, methyl, alkoxycarbonylmethyl where alkoxy is of 1 to 4 carbon atoms, phenyl or phenyl substituted by chlorine, methyl, methoxy, ethoxy, methylmercapto, ethylmercapto or phenylmercapto.
Claim 6
Dependent Claim
18 words
A dye as set forth in claim 1, where T 3 is a radical of the formula: ##STR83##
Claim 7
Dependent Claim
32 words
A dye as set forth in claim 5, where B 3 is hydrogen, methyl, methoxy or ethoxy and B 4 is hydrogen, methyl, chlorine or alkanoylamino of 1 to 4 carbon atoms.
Claim 8
Dependent Claim
66 words
A dye as set forth in claim 6, where B 1 and B 2 independently of one another are allyl, alkyl of 1 to 4 carbon atoms, or alkyl of 2 or 3 carbon atoms which is substituted by hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms.
Claim 9
Dependent Claim
62 words
A dye as set forth in claim 1, where T 1 is phenyl or phenyl substituted by chlorine, bromine, methyl, methoxy, ethoxy or phenylazo, T 2 is hydrogen, methyl, alkoxycarbonylmethyl where alkoxy is of 1 to 4 carbon atoms, phenyl or phenyl substituted by chlorine, methyl, methoxy, ethoxy, methylmercapto, ethylmercapto or phenylmercapto and T 3 is a radical of the formula ##STR84##
Claim 10
Dependent Claim
113 words
A dye as set forth in claim 1, of the formula ##STR85## where Y is hydrogen, methyl, methoxy of chlorine, Z is hydrogen, alkoxy of 1 to 4 carbon atoms, alkylmercapto of 1 to 4 carbon atoms, phenylmercapto, chlorine or methyl, B 4 is hydrogen, chlorine, methyl or alkanoylamino of 1 to 4 carbon atoms and B 1 and B 2 independently of one another are allyl, alkyl of 1 to 4 carbon atoms, or alkyl of 2 or 3 carbon atoms which is substituted by hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, alkoxycarbonyl where alkoxy is of 1 to 4 carbon atoms or alkanoyloxy of 1 to 4 carbon atoms.
Claim 11
Dependent Claim
11 words
A dye as claimed in claim 1, of the formula ##STR86##
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-06-10 | 1983-12-10 | 1984-06-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-06-10 | 1987-12-10 | 1988-06-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-06-10 | 1991-12-10 | 1992-06-10 | $7700.00 | Window Closed / Lapsed |