Fiber-reactive azo compounds, processes for their...

Details Fiber-reactive azo compounds, processes for their... Fiber-reactive azo compounds, processes for their...

1999-12-28

2001-01-23

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S635000, C534S638000, C534S642000, C558S029000, C564S341000

Reexamination Certificate

active

06177552

ABSTRACT:

The present invention is in the technical field of fiber-reactive azo dyes.
Azo compounds which possess a fiber-reactive group and have dye properties and can be used, for example, for dyeing cellulose fibers are known and extensively described in the literature, especially in patents and patent applications, for example in U.S. Pat. No. 4,754,023. However, these conventional azo dyes or, to be more precise, the dyeings obtainable therewith do not adequately meet the recent high expectations with regard to quality. More particularly, their fastness level and specifically the washoff of unfixed portions from the resulting dyeings leaves something to be desired with many of these dyes.
The present invention provides novel fiber-reactive azo compounds whose dyeings surprisingly meet these requirements.
The present invention accordingly relates to azo compounds, in particular monoazo, disazo and trisazo compounds, conforming to the general formula (1)
D−N=N−K  (1)
where
D is a group of the general formula (2)
 where:
R
21
is hydrogen, methyl, ethyl, methoxy, ethoxy or sulfo, preferably hydrogen, methyl, methoxy and sulfa and particularly preferably hydrogen;
R
22
is hydrogen, methyl, ethyl, methoxy, ethoxy or sulfa, preferably hydrogen or methoxy and particularly preferably hydrogen;
R
22
is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, or phenyl, preferably alkyl of 1 to 4 carbon atoms;
n is 2 or 3, preferably 2;
Y is vinyl or is a group of the general formula (3)
—CH
2
—CH
2
—Z  (3)
 where Z is a substituent which is eliminable by alkali with the formation of a vinyl group;
the SO
2
grouping on the benzene nucleus is preferably meta and particularly preferably para to the amino group;
K is the radical of a sulfa- and/or carboxy-containing compound which possesses the function of a singly or doubly coupleable coupling component or contains the latter as a moiety attached to the azo group, the coupling component being selected -from the following compounds: aminobenzenes, diaminobenzenes and phenols, in particular their sulfonic acids and carboxylic acids; naphthols, in particular their sulfonic acids and carboxylic acids; aminonaphthols, in particular their sulfonic acids; acylaminonaphthols, in particular their sulfonic acids, with the acyl radical of an alkanecarboxylic acid having 1 to 4 carbon atoms in the alkyl radical, or of an alkenecarboxylic acid having 2 to 4 carbon atoms in the alkenyl radical, or of an aromatic carboxylic acid, such as of benzoic acid, or of an aromatic sulfanic acid, such as of benzene- or toluenesulfonic acid, or of an N-substituted carbamic acid, such as of the N-phenylureido radical; dihydroxynaphthalenesulfonic acids; phenylazo- and naphthylazoaminonaphtholsulLonic acids; 5-pyrazolones and 5-aminopyrazoles; acetoacetylarylides; 2-hydroxy-6-pyridones; hydroxyquinolines; it also being possible for K to contain one or more fiber-reactive groups in addition to the substituents customary in water-soluble dyes, such as, for example, a group of the general formula —SO
2
—Y where Y has one of the abovementioned meanings or a 2-chloro- or 2-fluoro-4-morpholino-1,3,5-triazin-6-ylamino group or a 2-fluoro- or 2-chloro-4-amino-1,3,5-triazin-6-ylamino group whose amino group in the 4-position can be mono- or disubstituted by alkyl of 1 to 4 carbon atoms and/or phenyl and the phenyl radical is unsubstituted or substituted by substituents from the group comprising sulfo, carboxy, methyl, ethyl, methoxy, ethoxy, chlorine, bromine and —SO
2
—Y where Y has one of the abovementioned meanings.
Customary substituenis which may be present in the aromatic or heterocyclic radicals of K, as well as the aforementioned sulfo and carboxy groups, include for example substituents selected from the following group: alkyl of 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl or butyl, of which preferably ethyl and particularly methyl; a koxy of 1 to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy and butoxy, of which preferably ethoxy and especially methoxy; alkanoylamino of 2 to 5 carbon atoms, such as acetylamino and propionylamino; benzoylamino; sulfo-, carboxy-, methyl-, ethyl-, methoxy-, ethoxy- and/or chlorine-substituted benzoylamino; amino; mono(C
1
-C
4
-alkyl)amino, di(C
1
-C
4
-alkyl)amino, phenylamino and N-(C
1
-C
4
-alkyl)-N-phenylamino, whose alkyl groups may be substituted, for example by phenyl, sulfophenyl, hydroxy, sulfato, sulfo and carboxy, and whose phenyl groups may be substituted, as by chlorine, sulfo, carboxy, 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, diethylamino, phenylamino and sulfophenylamino; alkoxycarbonyl of 2 to 5 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl; alkylsulfonyl of 1 to 4 carbon atoms, such as methylsulfonyl and ethylsulfonyl; trifluoromethyl; nitro; cyano; ureido; hydroxy; sulfomethyl; halogen, such as fluorine, chlorine and bromine; carbamoyl which may be mono- and disubstituted by alkyl of 1 to 4 carbon atoms, N-phenylcarbamoyl and N-phenyl-N-(C
1
-C
4
-alkyl)carbamoyl, whose alkyl groups may be substituted, for example by hydroxy, sulfato, sulfo, carboxy, phenyl and sulfophenyl, and whose phenyl groups may be substituted, for example by methyl, ethyl, methoxy, ethyl, sulfo, carboxy, chlorine and cyano, for example N-methylcarbamoyl and N-ethylcarbamoyl; N-sulfamoyl which may be mono- or disubstituted by alkyl of 1 to 4 carbon atoms, N-phenylsulfamoyl and N-phenyl-N-alkylsulfamoyl having alkyl of 1 to 4 carbon atoms, whose alkyl may be substituted, for example by hydroxy, sulfato, sulfo, carboxy, phenyl and sulfophenyl, and whose phenyl groups may be substituted, for example by methyl, ethyl, methoxy, ethyl, sulfo, carboxy, chlorine and cyano, for example N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-(&bgr;-hydroxy-ethyl)sulfamoyl and N,N-di-(&bgr;-hydroxyethyl)sulfamoyl.
Alkali-eliminable substituents Z are, for example, halogen atoms, such as the bromine atom and chlorine atom, ester groups of organic carboxylic and sulfonic acids, such as an alkanoyloxy group of 2 to 5 carbon atoms, for example the acetoxy group, or a sulfobenzoyloxy, benzoyloxy, phenylsulfonyloxy or toluylsulfonyloxy group, furthermore, for example, phosphate, sulfato and thiosulfato groups, similarly dialkylamino groups containing alkyl groups of 1 to 4 carbon atoms each, such as dimethylamino and diethylamino. Y is preferably a vinyl group and in particular a &bgr;-sulfatoethyl group.
Sulfo groups are groups of the general formula —SO
3
M, carboxy groups are groups of the general formula —COOM, sulfato groups are groups of the general formula —OSO
3
M, thiosulfato groups are groups of the general formula —S—SO
3
M and phosphato groups are groups of the general formula —OPO
3
M
2
, in which
M is a hydrogen atom or a salt-forming metal atom, such as, in particular, an alkali metal atom, such as, for example, sodium, potassium or lithium.
Of the compounds according to the invention of the general formula (1), for example, those compounds may be mentioned in particular in which K is a radical of the formula (4a), (4b) (4c) , (4d) , (4e) , (4f), (4g), (4h), (4i) (4k), (4m), (4n) (4p), (4q), (4r), (4s) and (4t) below:
In these formulae, the symbols have the following meanings:
R
1
is hydrogen, carboxy, sulfo or a group of the general formula —SO
2
—Y where Y has the above meaning, or is a group of the general formula (a) or (b) or (c)
 where
R
15
is hydrogen, sulfo, carboxy or a group of the general formula —SO
2
—Y where Y is as defined above,
R
16
is hydrogen, alkyl of 1 to 4 carbon atoms, such as methyl and ethyl, alkoxy of 1 to 4 carbon atoms, such as methoxy and ethoxy, chlorine, bromine, carboxy, sulfo or nitro, preferably hydrogen, methoxy, ethoxy, methyl, ethyl, sulfo or carboxy,
R
17
is hydrogen, alkyl of 1 to 4 carbon

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