Hoechst Aktiengesellschaft

Ludwig Schlafer

Hartmut Springer

Werner H Russ

Reinhard Hahnle

Fritz Meininger

Konrad Opitz

Ernst Hoyer

Michael Kunze

Maria Kallay

Horst Tappe

Gunther Schwaiger

Heinz Uhrig

Peter Mischke

Walter Helmling

Dieter Oehme

Manfred Kuhn

Erwin Ungermann

Karl-Heinz Flemmig

Johannes Jeths

Water-soluble monoazo compounds conforming to the general formula (1) ##STR1## where D is monosulfo- or disulfo-phenyl, which may each be substituted by lower alkyl, lower alkoxy, halogen, carboxy and/or lower alkanoylamino, or is mono- or di- or trisulfonaphthyl, K as the radical of a coupling component is para-phenylene, which may be substituted by lower alkyl, lower alkoxy, halogen, lower alkanoylamino, ureido, carbamoyl and/or sulfo, or is 1,4-naphthylene, which may be substituted by 1 or 2 sulfo groups and/or a lower alkoxy group, R is hydrogen or lower alkyl, A is phenylene or a direct bond, W is a direct bond or lower alkylene or an amino group substituted by lower alkyl, although A and W are not both a direct bond, and the group --SO.sub.2 --X is a fiber-reactive group of the vinyl sulfone series. The azo compounds of the formula (1) are fiber-reactive and have very good dyestuff properties. They dye hydroxy- and/or carboxamido-containing material, in particular fiber material, for example cellulose fiber materials, wool and synthetic polyamide fibers, in strong, bright, fast shades. In particular they are suitable for discharge and resist printing.

Water-soluble compounds having a fiber-reactive group of the vinyl

There are described monoazo compounds which exhibit fiber-reactive properties and dye hydroxy- and/or carboxamido-containing materials, in particular fiber materials, such as, for example, cellulose fiber materials and wool, in shades of high color strength and good fastness properties and can also be used in particular for resist and discharge printing. They have the formula (1) ##STR1## in which: A is substituted or unsubstituted phenylene or unsubstituted or sulfo-substituted naphthylene, the groups X--SO.sub.2 -- and --SO.sub.2 X.sup.1 are fiber-reactive groups from the vinylsulfonyl series, n is the number 1 or 2, M is hydrogen or an alkali metal, R is hydrogen or a lower alkyl, W is phenylene or lower alkylene, B is lower alkyl and one group --SO.sub.3 M is bound to the 8-naphthol radical in the 3- or 4-position.

Water-soluble monoazo compounds containing fiber-reactive groups of

Azo compounds with fiber-reactive dye properties, having defined general formula (1) below, are described which dye fiber materials containing hydroxy and/or carboxamide groups, such as synthetic polyamide fibers or wool, and especially cellulose fiber materials such as cotton, in strong, fast, predominantly red shades. ##STR1## in which: X is vinyl or .beta.-sulfatoethyl;

Water-soluble azo compounds, having a fiber-reactive group of the

Water-soluble disazo compounds, processes for their preparation of their use as dyestuffs Disazo compounds of the general formula (1) defined below, ##STR1## which have fiber-reactive properties and are suitable as useful dyestuffs for dyeing material containing carboxamide groups and/or material containing hydroxy groups, such as fiber material, for example wool and cellulose fiber materials, are described. In formulas (1):

Water-soluble disazo compounds, having a fiber-reactive group of the

Water-soluble azo compounds which have fiber-reactive dyestuff properties and dye materials containing carboxamide and/or hydroxyl groups, such as fiber materials, in particular cellulose fiber materials, in strong, fast, predominantly bluish-tinged red to orange shades; they correspond to the general formula (1) ##STR1## in which: M is a hydrogen atom or an alkali metal;

Water-soluble azo compounds containing a sulfo-naphthol as a coupling

Compounds according to the general formula ##STR1## in which: D is phenyl, optionally substituted by sulfo, carboxy, alkyl, alkoxy, alkanoylamino and/or chlorine, at least by sulfo or carboxy, or is a sulfosubstituted naphthyl;

Water-soluble disazo compounds, containing a vinylsulfonyl or

Water-soluble monoazo compounds of the general formula (1) which dye in fast, mainly red shades materials which contain carboxamide and/or hydroxy groups, preferably in the form of fibers, in particular cellulose fiber materials. ##STR1## in which: Y is .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-chloroethyl, vinyl or .beta.-sulfatoethyl,

Water-soluble monoazo compounds containing a p-aminophenylamino- and

Water-soluble azo compounds which have fiber-reactive and dye properties and dye carboxamido- and/or hydroxyl-containing materials, such as fiber materials, in particular cellulose fiber materials, in strong, predominantly bluish red to orange hues which have good fastness properties; they conform to the general formula (1) ##STR1## in which the symbols have the following meaning: M is a hydrogen atom or an alkali metal,

Water-soluble monoazo compounds having fiber-reactive groups of the

Water-soluble monoazo compounds according to the general formula (1) below having valuable fiber-reactive dyestuff properties which dye carboxamido- and/or hydroxy-containing materials, in particular cellulose fibers, in fast yellow to orange hues. ##STR1## in which the symbols denote: M is hydrogen or an alkali metal,

Water soluble naphthylazopyrazolone dyestuffs having fiber-reactive

Water-soluble monoazo compounds corresponding to the following general formula (1) which have valuable fiber-reactive dyestuff properties and which dye materials, in particular cellulose fibers, containing carboxamide and/or hydroxy groups in fast, yellow shades. ##STR1## in which the symbols have the following meanings: D is a benzene ring or a radical of the formula ##STR2## R.sup.1 and R.sup.3, independently of one another, are both hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine, bromine, carboxy or sulfo,

Water-soluble monoazopyrazolone dyestuffs having fiber reactive groups

Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted by lower alkoxy, lower alkyl, chlorine, sulfo and carboxy, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;

Water-soluble fiber-reactive aminotriazine and vinylsulfone containing

Water-soluble azo compounds having useful fiber-reactive dye properties conforming to the general formula ##STR1## in which: A is phenylene which may be substituted or unsubstituted, or is a radical of the formula ##STR2## in which W is a direct bond or a radical of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R* denotes hydrogen, nitro, sulfo, carboxy, methyl, ethyl, methoxy or ethoxy;

Reactive water-soluble azo dyes containing carboxy- or

Water-soluble disazo compounds having useful fiber-reactive dye properties, which conform to the general formula (1) defined hereinafter and dye carboxamido- and/or hydroxy-containing materials in fast shades. Fast dyeings on cellulose fiber materials can also be obtained in a weakly acid to neutral pH range, for example together with disperse dyes for dyeing a polyester fiber portion. ##STR1## in which: A is phenylene which may be substituted by methyl, ethyl, methoxy, chlorine or sulfo, or is a radical of the formula ##STR2## in which G is a direct bond or a group of the formula --CH.dbd.CH-- or --NH--CO--NH-- and R.sup.1 and R.sup.2 are each independently of the other hydrogen, sulfo, methyl, ethyl, methoxy or ethoxy;

Water-soluble disazo compounds containing 3-carboxy or

Water-soluble disazo compounds of the formula ##STR1## in which D is a benzene ring or a naphthalene ring which can both be substituted by substituents from the group consisting of chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, carboxy and sulfo, X is the vinyl group or a .beta.-sulfatoethyl group, R is a .beta.-sulfatoethylsulfonyl, 3-(.beta.-chloroethylsulfonyl)-benzoyl, 4-(.beta.-chloroethylsulfonyl)-benzoyl, 3-(.beta.-chloroethylsulfonylmethyl)-benzoyl, 4-(.beta.-chloroethylsulfonylmethyl)-benzoyl,4-(.beta.-chloroethylsulfonyl )-cinnamoyl, 3-(N-methyl-N-.beta.chloroethylsulfonyl)-aminobenzoyl or 4-(N-methyl-N-.beta.-chloroethylsulfonyl)-aminobenzoyl group, m is the number 1 or 2 and M denotes a hydrogen atom or an alkali metal. The disazo compounds are suitable for use as dyes having fiber-reactive properties for dyeing hydroxy- and/or carboxamido-containing fiber material, such as in particular cellulose fiber materials and polyamide fiber materials. These disazo compounds have good solubility and stability in printed pastes and dyebaths; they exhibit a high color strength and a good color buildup; and they produce, in high degrees of fixation, navy to black dyeings and prints with good fastness to, inter alia, light, wash, seawater, chlorinated water, acid, and alkali, and these dyeings and prints have stability toward copper ions.

Water-soluble disazo compounds containing the

Water-soluble compounds having fiber-reactive dye properties of the general formula ##STR1## in which A is an alkylene of 2 to 6 carbon atoms or a phenylene which can be substituted by 1 or 2 substituents, or is a radical of the formula ##STR2## in which W is a direct bond or a bridge member and the R' and R* each denote hydrogen, chlorine, methyl, methoxy, ethoxy, carboxy or sulfo;

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Ludwig Schlafer