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US4042578A Expired / Lapsed US ⏱️ 0.0 years remaining

Azo dyes having 2,6-diaminopyridine derivatives as coupling components

Assignee: BASF SE
•
Filing: 1973-03-07
•
Granted: 1977-08-16
•
Expires: 1993-03-07
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Abstract

Abstract Azo dyes having 2,6-diaminopyridine derivatives as coupling components which preferably bear cyano or carbamoyl as substituents in the 3-position. The dyes give brilliant yellow to blue colorations, particularly on synthetic polyesters, which are distinguished by outstanding fastness properties.

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; C07D213/72; C07D213/74; C07D213/76; C07D213/77; C07D213/78; C07D213/81; C07D213/82; 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; C09B43/00; C09B43/18; C09B43/20; C09B43/202

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 521 words
A dye of the formula ##STR801## wherein: D is phenyl substituted by chlorine, bromine, trifluoromethyl, methyl, methoxy, nitro, cyano, methylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2 to 5 carbon atoms, carbo-β-alkoxy-ethoxy, said alkoxy having 1 to 4 carbon atoms, or N,N-dialkyl- or N-monoalkyl-substituted sulfamoyl, each alkyl having 1 to 4 carbon atoms; phenylazophenyl; phenylazophenyl substituted by methyl, chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by 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 or carbalkoxy of a total of 2 to 5 carbon atoms; or thiadiazolyl substituted by phenyl, methyl, chlorine, bromine, methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 to 4 carbon atoms; R is alkyl of 1 to 3 carbon atoms; X is carbamoyl or cyano; R 1 and R 2 may be the same or different with the proviso that one of R 1 and R 2 is C 6 H 5 ; ##STR802## (CH 2 ) 3 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 6 OH; ##STR803## (CH 2 ) 3 OC 2 H 4 OR 7 , (CH 2 ) 3 (OC 2 H 4 ) q OR 8 , (CH 2 ) 3 OR 9 ; ##STR804## C 2 H 4 OC 6 H 5 , C 2 H 4 OC 6 H 4 CH 3 ; ##STR805## and the other of R 1 and R 2 is hydrogen; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, formyloxy, acetoxy, propionyloxy, carboxy, cyclohexoxy, benzyloxy, phenylethoxy, phenoxy or pyrrolidonyl; cyclohexyl; methylcyclohexyl; benzyl; phenylethyl; β-phenyl-β-hydroxyethyl; phenyl; tolyl; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 OC 6 H 5 --CH 3 ; (CH 2 ) 3 O(CH 2 ) 4 OH; ##STR806## (CH 2 ) 3 OC 2 H 4 OCH 3 ; (CH 2 ) 3 OC 2 H 4 OC 6 H 5 ; ##STR807## (CH 2 ) 3 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 6 OH; ##STR808## (CH 2 ) 3 OC 2 H 4 OR 7 ; (CH 2 ) 3 (oc 2 H 4 ) q OR 8 ; ##STR809## C 2 H 4 OC 6 H 4 CH 3 ; ##STR810## R 3 is alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl; R 4 is hydrogen, alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl; R 5 is hydrogen or hydroxyl; R 6 is hydrogen, alkyl of 1 to 4 carbon atoms, methoxy, ethoxy or chloro; one of R 3 to R 5 providing a hydroxy group; R 7 is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl or methylphenyl; R 8 is hydrogen, alkyl of one to four carbon atoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; R 9 is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; m is 1 or 2; n is zero, 1 or 2; q is 2, 3 or 4; and p is 1, 2, 3 or 4.
Claim 2
Dependent Claim 521 words
A dye of the formula ##STR801## wherein: D is phenyl substituted by chlorine, bromine, trifluoromethyl, methyl, methoxy, nitro, cyano, methylsulfonyl, phenylsulfonyl, carbalkoxy of a total of 2 to 5 carbon atoms, carbo-β-alkoxy-ethoxy, said alkoxy having 1 to 4 carbon atoms, or N,N-dialkyl- or N-monoalkyl-substituted sulfamoyl, each alkyl having 1 to 4 carbon atoms; phenylazophenyl; phenylazophenyl substituted by methyl, chlorine, bromine or nitro; benzthiazolyl; benzthiazolyl substituted by 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 or carbalkoxy of a total of 2 to 5 carbon atoms; or thiadiazolyl substituted by phenyl, methyl, chlorine, bromine, methylmercapto, ethylmercapto or alkoxycarbonylethylmercapto, said alkoxy having 1 to 4 carbon atoms; R is alkyl of 1 to 3 carbon atoms; X is carbamoyl or cyano; R 1 and R 2 may be the same or different with the proviso that one of R 1 and R 2 is C 6 H 5 ; ##STR802## (CH 2 ) 3 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 6 OH; ##STR803## (CH 2 ) 3 OC 2 H 4 OR 7 , (CH 2 ) 3 (OC 2 H 4 ) q OR 8 , (CH 2 ) 3 OR 9 ; ##STR804## C 2 H 4 OC 6 H 5 , C 2 H 4 OC 6 H 4 CH 3 ; ##STR805## and the other of R 1 and R 2 is hydrogen; alkyl of 1 to 8 carbon atoms; alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 8 carbon atoms, formyloxy, acetoxy, propionyloxy, carboxy, cyclohexoxy, benzyloxy, phenylethoxy, phenoxy or pyrrolidonyl; cyclohexyl; methylcyclohexyl; benzyl; phenylethyl; β-phenyl-β-hydroxyethyl; phenyl; tolyl; CH 2 CH 2 OCH 2 CH 2 OH; (CH 2 ) 3 OC 6 H 5 --CH 3 ; (CH 2 ) 3 O(CH 2 ) 4 OH; ##STR806## (CH 2 ) 3 OC 2 H 4 OCH 3 ; (CH 2 ) 3 OC 2 H 4 OC 6 H 5 ; ##STR807## (CH 2 ) 3 OCH 2 CH 2 OH; (CH 2 ) 3 O(CH 2 ) 6 OH; ##STR808## (CH 2 ) 3 OC 2 H 4 OR 7 ; (CH 2 ) 3 (oc 2 H 4 ) q OR 8 ; ##STR809## C 2 H 4 OC 6 H 4 CH 3 ; ##STR810## R 3 is alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl; R 4 is hydrogen, alkyl of one to three carbon atoms, hydroxymethyl or hydroxyethyl; R 5 is hydrogen or hydroxyl; R 6 is hydrogen, alkyl of 1 to 4 carbon atoms, methoxy, ethoxy or chloro; one of R 3 to R 5 providing a hydroxy group; R 7 is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl or methylphenyl; R 8 is hydrogen, alkyl of one to four carbon atoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; R 9 is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl; m is 1 or 2; n is zero, 1 or 2; q is 2, 3 or 4; and p is 1, 2, 3 or 4.
Claim 3
Dependent Claim 70 words
A dye as claimed in claim 1 of the formula ##STR811## wherein: Y is nitro, cyano, chloro, bromo, carbomethoxy, carboethoxy, β-methoxycarboethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy or phenylazo; Y 1 is hydrogen, nitro, chloro, bromo, cyano, methyl, methoxy, carbomethoxy, carboethoxy, methylsulfonyl or ethylsulfonyl; and Y 2 is hydrogen, chloro, bromo, cyano, methyl, methoxy, carbomethoxy or carboethoxy; and R 1 and R 2 have the same meanings as given in claim 1.
Claim 4
Dependent Claim 11 words
A dye as claimed in claim 1 wherein X is cyano.
Claim 5
Dependent Claim 140 words
A dye as claimed in claim 1 wherein: X is cyano; said one of R 1 and R 2 is C 6 H 5 ; ##STR812## (CH 2 ) 3 OC 2 H 4 OH, (CH 2 ) 3 O(CH 2 ) 6 OH, ##STR813## (CH 2 ) 3 OC 2 H 4 OCH 2 C 6 H 5 ; (CH 2 ) 3 (OC 2 H 4 ) 2 OR 8 ; ##STR814## (CH 2 ) 3 OC 6 H 5 ; (CH 2 ) 3 OCH 2 C 6 H 5 or (CH 2 ) 3 OC 2 H 4 C 6 H 5 ; and said other of R 1 and R 2 is hydrogen; or alkyl of 2 to 8 carbon atoms substituted by hydroxy, alkoxy of 1 to 4 carbon atoms, formyloxy, acetoxy or propionyloxy.
Claim 6
Dependent Claim 6 words
The dye of the formula ##STR815##
Claim 7
Dependent Claim 6 words
The dye of the formula ##STR815##
Claim 8
Dependent Claim 6 words
The dye of the formula ##STR816##
Claim 9
Dependent Claim 6 words
The dye of the formula ##STR816##
Claim 10
Dependent Claim 6 words
The dye of the formula ##STR817##
Claim 11
Dependent Claim 6 words
The dye of the formula ##STR817##
Claim 12
Dependent Claim 6 words
The dye of the formula ##STR818##
Claim 13
Dependent Claim 6 words
The dye of the formula ##STR818##

References Cited (Backward Citations)

SU270987A1 Cited
US2148705A Cited
US2145579A Cited
US2068353A Cited
US2681906A Cited
US3531457A Cited
US3531458A Cited
DE2062717A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-15 1981-02-14 1981-08-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-15 1985-02-14 1985-08-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-15 1989-02-14 1989-08-16 $7700.00 Window Closed / Lapsed

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