US 3,998,802 AGranted

Azo dye with a 3-cyano- or 3-carbamoyl-4-methyl-2,6-diamino-pyridine coupling component

AssigneeBASF SE

InventorsJohannes Dehnert, Gunther Lamm

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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.sup.1 and R.sup.2 + R.sup.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.

Claims16

Dependent claims

A dye of the formula

where
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-.beta.-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, .beta.-hydroxyethyl, .beta.-hydroxyethoxy, methoxy or ethoxy;
cyclohexyl;
hydroxycyclohexyl;
.omega.-N-pyrrolidonylalkyl, said alkyl having 2 or 3 carbon atoms;
CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH;
(CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH;
(CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3 ;
(CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.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.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH;
(CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH;
or (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3.

26 more elements

Dependencies are inferred from the claim text.

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Abstract

A dye of the formula

where
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-.beta.-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, .beta.-hydroxyethyl, .beta.-hydroxyethoxy, methoxy or ethoxy;
cyclohexyl;
hydroxycyclohexyl;
.omega.-N-pyrrolidonylalkyl, said alkyl having 2 or 3 carbon atoms;
CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH;
(CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH;
(CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3 ;
(CH.sub.2).sub.3 OC.sub.2 H.sub.4 OC.sub.6 H.sub.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.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OH;
(CH.sub.2).sub.3 O(CH.sub.2).sub.4 OH;
or (CH.sub.2).sub.3 OC.sub.2 H.sub.4 OCH.sub.3.

26 more elements