Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2000-05-22
2002-09-03
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S617000, C534S641000, C534S642000, C540S126000, C544S076000, C544S189000, C544S197000, C544S198000, C008S549000
Reexamination Certificate
active
06444794
ABSTRACT:
This invention relates to the technical field of fiber-reactive dyes.
The PCT Patent Application Publications Nos. WO 90/13603 and WO 90113604 disclose fiber-reactive dyes which have a fiber-reactive group of the vinyl sulfone series and also an s-triazinylamino radical substituted by a cyanamide group.
The commercial practice of dyeing with reactive dyes has recently led to heightened expectations with regard to the quality of the dyeings and the economics of the dyeing process. There consequently continues to be a demand for novel fiber-reactive dyes with improved properties, especially application properties. More particularly, even very short liquor ratios shall provide dyeings having very high color strength, good wash-off properties and high levelness.
The present invention, then, provides novel and useful fiber-reactive dyes of the hereinbelow indicated and defined general formula (1) which have the required application properties. The novel, inventive dyes have the general formula (1)
where
F is the residue of a monoazo, disazo or polyazo dye or of a derived heavy metal complex azo dye or of an anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye;
R
x
is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, such as methyl or ethyl, which may be substituted by halogen, such as chlorine and bromine, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkoxycarbonyl of 2 to 5 carbon atoms, carboxyl, sulfamoyl, sulfo or sulfato, preferably methyl or ethyl and especially a hydrogen atom;
n is 1 or 2, preferably 1;
Q is a group of the general formula (2)
where
R
z
is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, such as especially methyl or ethyl, which may be substituted by halogen, such as chlorine and bromine, hydroxyl, cyano, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, carboxyl, sulfamoyl, sulfo, sulfato, phenyl or phenyl substituted by substituents selected from the group consisting of halogen, such as chlorine and bromine, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkyl of 1 to 4 carbon atoms, such as methyl, sulfo and carboxyl, or is a cyclohexyl radical, a phenyl radical or a phenyl radical substituted by substituents selected from the group consisting of halogen, such as chlorine and bromine, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, alkyl of 1 to 4 carbon atoms, such as methyl, sulfo and carboxyl, is alkyl-SO
2
—Y, alkyl-Het-alkyl-SO
2
—Y, where alkyl represents an alkyl group of 1 to 4 carbon atoms, Het is —O—, —NH—, —N(alkyl)— where alkyl is as defined above, —S—or SO
2
and Y is as defined below;
A is zero or 1, and
B is 1 or 2,
the sum of (A+B) is 2 and in the event of B being 2 the groups of the formula —W— being identical to or different from each other;
V is a direct bond or an alkylene group or is a substituted or unsubstituted arylene radical or an alkylene-arylene or arylene-alkylene or alkylene-arylene-alkylene or arylene-alkylene-arylene radical or an arylene-arylene radical interrupted by one of the hetero groups indicated hereinafter, where the alkylene radicals are alkylene radicals of 1 to 8, preferably 2 to 6, especially 2 to 4, carbon atoms and may be substituted, for example by sulfo, carboxyl, sulfato and/or phosphato, and the arylene radicals are substituted or unsubstituted phenylene or naphthylene radicals, and where the alkylene radicals may be interrupted by 1 or more, such as 2 or 3, hetero groups, such as —NH—, —N(R)— where R is alkyl of 1 to 4 carbon atoms which may be sulfo-, carboxyl-, sulfato-, phenyl- or sulfophenyl-substituted, —O—, —S—, —SO
2
—, —CO—, —SO
2
—NH—, —NH—SO
2
—, —NH—CO— and —CO—NH—, and the alkylene and arylene moieties in the combined alkylene/arylene radicals may in each case be separated from each other by such a hetero group;
y is 0, 1 or 2, preferably 1;
z is 1 or 2, preferably 1;
h is for y=2 a nitrogen atom or for y=1 a group of the formula —NH—, —N(R)— where R is as defined above, —NH—CO—NH—, —NH—CO— or —CO—NH— or preferably a direct bond;
Y is vinyl or is an ethyl group &bgr;-substituted by an alkali-eliminable substituent, such as &bgr;-sulfatoethyl, &bgr;-thiosulfatoethyl or &bgr;-phosphatoethyl or a &bgr;-alkanoyloxyethyl group having 2 top carbon atoms in the alkanol radical, such as &bgr;-acetyloxyethyl, or &bgr;-benzoyloxyethyl, &bgr;-(sulfobenzoyloxy)ethyl or &bgr;-(p-toluenesulfonyloxy)ethyl or &bgr;-haloethyl, such as &bgr;-bromoethyl or &bgr;-chloroethyl, and is preferably vinyl and especially &bgr;-sulfatoethyl, Y may also be hydroxyl if the hydroxyl group is subsequently converted with sulfuric acid or chlorosulfonic acid into a sulfato group, in which case the —SO
2
—Y group or groups may be attached to an aromatic carbon atom of F or V via an alkylene radical of 1 to 4 carbon atoms, such as methyl, or via an alkylamino group of 1 to 4 carbon atoms, such as methylamino or ethylamino.
F is preferably the residue of a mono- or disazo dye or the residue of a metal complex azo dye, as of an o,o′ 1:1 copper complex monoazo or disazo dye or of a triphendioxazine, of an anthraquinone or of a phthalocyanine dye, as of a copper phthalocyanine dye.
The basic structure of F may contain customary organic dye substituents. Examples of such substituents are alkyl groups of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, preferably ethyl and especially methyl; alkoxy groups of 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and butoxy, preferably ethoxy and especially methoxy; acylamino groups of 2 to 8 carbon atoms, such as acetylamino, propionylamino or benzoylamino; primary and mono- or disubstituted amino groups, substituents being for example alkyl groups of 1 to 4 carbon atoms and/or phenyl groups, such as monoalkylamino and dialkylamino groups having 1 to 4 carbon atoms in the alkyl radical, phenylamino or N—(C
1
-C
4
-alkyl)-N-phenylamino groups, which alkyl radicals may be further substituted, for example by phenyl, sulfophenyl, hydroxyl, sulfato, sulfo and carboxyl, and which phenyl groups may be further substituted, as by chlorine, sulfo, carboxyl, methyl and/or methoxy, for example methylamino, ethylamino, propylamino, isopropylamino, butylamino, N,N-di(&bgr;-hydroxyethyl)amino-, N,N-di(&bgr;-sulfatoethyl)-amino, sulfobenzylamino, N,N-di(sulfobenzyl)amino and diethylamino groups and also phenylamino and sulfophenylamino groups; alkoxycarbonyl groups having an alkyl radical of 1 to 4 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfonyl groups of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl; trifluoromethyl, nitro and cyano groups; halogen atoms, such as fluorine, chlorine and bromine; carbamoyl groups which may be mono- and disubstituted by alkyl of 1 to 4 carbon atoms, in which case the alkyl radicals may in turn be substituted, for example by hydroxyl, sulfato, sulfo, carboxyl, phenyl and sulfophenyl, for example N-methylcarbamoyl and N-ethylcarbamoyl; sulfamoyl groups which may be mono- or disubstituted by alkyl groups of 1 to 4 carbon atoms, and N-phenyl-N-alkylsulfamoyl groups having an alkyl group of 1 to 4 carbon atoms, in which case these alkyl groups may in turn be substituted by hydroxyl, sulfato, sulfo, carboxyl, phenyl and sulfophenyl, for example N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-(&bgr;-hydroxyethyl)sulfamoyl and N,N-di(&bgr;-hydroxyethyl)sulfamoyl; N-phenylsulfamoyl, ureido, hydroxyl, carboxyl, sulfomethyl and sulfo groups.
The dye residue F is preferably substituted by one or more, as by 2 to 4, sulfo groups and may further preferably contain substituents selected from the group consisting of sulfo, methyl, ethyl, methoxy, ethoxy, alkanoylamino of 2 to 5 carbon atoms, such as acetylamino, benzoylamino, amino, chlorine, bromine, ureido, hydroxyl, carboxyl and sulfomethyl.
Water-solubilizin
Dannheim Jörg
Ehrenberg Stefan
DyStar Textilfarben GmbH & Co. Deutschland KG
Powers Fiona T.
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