US3998802A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Azo dye with a 3-cyano- or 3-carbamoyl-4-methyl-2,6-diamino-pyridine coupling component
Assignee: BASF SE
•
Filing: 1974-01-24
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Granted: 1976-12-21
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Expires: 1994-01-24
Abstract
Abstract Azo dyes of the formula ##STR1## wherein D is the diazo component, the R substituents represent hydrogen or various organic radicals and X is cyano or carbamoyl. The R members are hydrogen, an alkyl or other aliphatic group as well as other selected groups including heterocyclic rings formed by R + R 1 and R 2 + R 3 with the nitrogen atom. The dyes are eminently suitable for dyeing polyamides, cellulose esters, acrylonitrile polymers and particularly polyesters brilliant yellow to blue shades of excellent fastness properties to dry-heat pleating and setting and also to light.
Inventors
- 👤 Johannes Dehnert
- 👤 Gunther Lamm
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:44
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/84; C07D213/85; C09; C09B; C09B29/00; C09B29/34; C09B29/36; C09B29/3604; C09B29/3617; C09B29/3621; C09B29/3639; C09B31/00; C09B31/02; C09B31/12; C09B31/14; C09B31/153
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
6 words
A dye of the formula where
Claim 2
Dependent Claim
6 words
A dye of the formula where
Claim 3
Dependent Claim
341 words
D is phenyl substituted by chlorine, bromine, methyl, trifluoromethyl, methoxy, nitro, cyano, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2 to 5 carbon atoms, carbo-β-alkoxyethoxy, said alkoxy having 1 to 4 carbon atoms, or N,N-dialkyl-substituted sulfamoyl, said alkyl having 1 to 3 carbon atoms; phenylazophenyl; phenylazophenyl substituted by chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by chlorine, methoxy, ethoxy, nitro, cyano, methylsulfonyl or ethylsulfonyl; benzisothiazolyl substituted by chlorine, bromine, cyano or nitro; thiazolyl substituted by cyano or nitro; thienyl substituted by methyl, cyano, nitro, carbalkoxy of a total of 2 to 5 carbon atoms; or thiadiazolyl substituted by phenyl, ethyl, chlorine, bromine, methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 to 4 carbon atoms; X is cyano or carbamoyl; one R is allyl; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 6 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, carboxy, carbalkoxy of a total of 2 to 5 carbon atoms, alkanoyloxy of 1 to 4 carbon atoms, acetoacetoxy, phenoxyacetyl, phenylacetyl, amino, alkylamino or dialkylamino of a total of 1 to 8 carbon atoms; benzyl, phenylethyl phenyl substituted by chlorine, methyl, ethyl, β-hydroxyethyl, β-hydroxyethoxy, methoxy or ethoxy; cyclohexyl; hydroxycyclohexyl; ω-N-pyrrolidonylalkyl, said alkyl having 2 or 3 carbon atoms; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 4 OH; (CH 2 ) 3 OC 2 H 4 OCH 3 ; (CH 2 ) 3 OC 2 H 4 OC 6 H 5 ; or ##STR671## and the other R is hydrogen; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 6 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, carboxy, carbalkoxy of a total of 2 to 5 carbon atoms, alkanoyloxy of 1 to 4 carbon atoms, amino, alkylamino or dialkylamino of a total of 1 to 8 carbon atoms; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 4 OH; or (CH 2 ) 3 OC 2 H 4 OCH 3 .
Claim 4
Dependent Claim
341 words
D is phenyl substituted by chlorine, bromine, methyl, trifluoromethyl, methoxy, nitro, cyano, methylsulfonyl, ethylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2 to 5 carbon atoms, carbo-β-alkoxyethoxy, said alkoxy having 1 to 4 carbon atoms, or N,N-dialkyl-substituted sulfamoyl, said alkyl having 1 to 3 carbon atoms; phenylazophenyl; phenylazophenyl substituted by chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by chlorine, methoxy, ethoxy, nitro, cyano, methylsulfonyl or ethylsulfonyl; benzisothiazolyl substituted by chlorine, bromine, cyano or nitro; thiazolyl substituted by cyano or nitro; thienyl substituted by methyl, cyano, nitro, carbalkoxy of a total of 2 to 5 carbon atoms; or thiadiazolyl substituted by phenyl, ethyl, chlorine, bromine, methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 to 4 carbon atoms; X is cyano or carbamoyl; one R is allyl; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 6 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, carboxy, carbalkoxy of a total of 2 to 5 carbon atoms, alkanoyloxy of 1 to 4 carbon atoms, acetoacetoxy, phenoxyacetyl, phenylacetyl, amino, alkylamino or dialkylamino of a total of 1 to 8 carbon atoms; benzyl, phenylethyl phenyl substituted by chlorine, methyl, ethyl, β-hydroxyethyl, β-hydroxyethoxy, methoxy or ethoxy; cyclohexyl; hydroxycyclohexyl; ω-N-pyrrolidonylalkyl, said alkyl having 2 or 3 carbon atoms; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 4 OH; (CH 2 ) 3 OC 2 H 4 OCH 3 ; (CH 2 ) 3 OC 2 H 4 OC 6 H 5 ; or ##STR671## and the other R is hydrogen; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 6 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, carboxy, carbalkoxy of a total of 2 to 5 carbon atoms, alkanoyloxy of 1 to 4 carbon atoms, amino, alkylamino or dialkylamino of a total of 1 to 8 carbon atoms; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 4 OH; or (CH 2 ) 3 OC 2 H 4 OCH 3 .
Claim 5
Dependent Claim
23 words
A dye according to the formula in claim 1, wherein D is phenyl substituted by nitro, cyano, carbomethoxy, methylsulfonyl, ethylsulfonyl, chlorine or bromine.
Claim 6
Dependent Claim
57 words
A dye according to the formula in claim 1 wherein D is benzisothiazolyl substituted by nitro, cyano, chlorine or bromine; thiazolyl substituted by nitro; thiadiazolyl substituted by methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 or 2 carbon atoms, thienyl substituted by cyano, nitro, methyl or carbomethoxy; benzthiazolyl; or benzthiazolyl substituted by methoxy, ethoxy, chlorine or nitro.
Claim 7
Dependent Claim
13 words
A dye according to the formula in claim 1, wherein X is cyano.
Claim 8
Dependent Claim
79 words
A dye according to the formula in claim 1, wherein one R is hydrogen, hydroxyalkyl of 2 to 6 carbon atoms or CH 2 CH 2 OCH 2 CH 2 OH and the other R is phenylethyl, CH 2 CH 2 OCH 2 CH 2 OH, ##STR672## (CH 2 ) 3 O(CH 2 ) 4 OH, (CH 2 ) 3 OC 2 H 4 OCH 3 or (CH 2 ) 3 OC 2 H 4 OC 6 H.sub. 5.
Claim 9
Dependent Claim
6 words
The dye having the formula ##STR673##
Claim 10
Dependent Claim
6 words
The dye having the formula ##STR673##
Claim 11
Dependent Claim
6 words
The dye having the formula ##STR674##
Claim 12
Dependent Claim
6 words
The dye having the formula ##STR674##
Claim 13
Dependent Claim
6 words
The dye having the formula ##STR675##
Claim 14
Dependent Claim
6 words
The dye having the formula ##STR675##
Claim 15
Dependent Claim
6 words
The dye having the formula ##STR676##
Claim 16
Dependent Claim
6 words
The dye having the formula ##STR676##
Claim 17
Dependent Claim
6 words
The dye having the formula ##STR677##
Claim 18
Dependent Claim
6 words
The dye having the formula ##STR677##
Claim 19
Dependent Claim
6 words
The dye having the formula ##STR678##
Claim 20
Dependent Claim
6 words
The dye having the formula ##STR678##
Claim 21
Dependent Claim
6 words
The dye having the formula ##STR679##
Claim 22
Dependent Claim
6 words
The dye having the formula ##STR679##
Claim 23
Dependent Claim
6 words
The dye having the formula ##STR680##
Claim 24
Dependent Claim
6 words
The dye having the formula ##STR680##
Claim 25
Dependent Claim
6 words
The dye having the formula ##STR681##
Claim 26
Dependent Claim
6 words
The dye having the formula ##STR681##
Claim 27
Dependent Claim
6 words
The dye having the formula ##STR682##
Claim 28
Dependent Claim
6 words
The dye having the formula ##STR682##
Claim 29
Dependent Claim
6 words
The dye having the formula ##STR683##
Claim 30
Dependent Claim
6 words
The dye having the formula ##STR683##
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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) | 1979-12-21 | 1980-06-21 | 1980-12-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-12-21 | 1984-06-21 | 1984-12-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-12-21 | 1988-06-21 | 1988-12-21 | $7700.00 | Window Closed / Lapsed |