Hoechst Aktiengesellschaft

Ernst Hoyer

Fritz Meininger

Rudolf Fass

Hans H Steuernagel

Ludwig Schlafer

Gunther Schwaiger

Willi Steckelberg

Rudolf Schickfluss

Walter Deucker

Joachim W Otten, Deceased

By Anna Rudolph Nee Otten, Heir

By Ursula Otten, Heir

Folker Kohlhaas

Walter Noll

August Bauer

Dieter Wagner

Water-soluble copper complex disazo compounds with fiber-reactive dyestuff properties of the general formula ##STR1## in which m and n are the number zero or 1;

Water-soluble copper complex disazo compounds containg a chloro

Water-soluble disazo compounds of the general formula ##STR1## in which D.sub.1 and D.sub.2 are each a phenylene or naphthylene radical which can be substituted by 1 or 2 substituents from the group consisting of 1 chlorine, 1 bromine, 2 sulfo, 2 carboxyl, 2 alkyl of 1 to 4 carbon atoms and 2 alkoxy of 1 to 4 carbon atoms, R' and R' each denote an amino or hydroxyl group, R.sup.+ and R* each represent methyl, carboxyl or lower carbalkoxy, R.sup.1 and R.sup.3 are each hydrogen, lower alkyl, lower alkoxy, chlorine or bromine, R.sup.2 and R.sup.4 each denote hydrogen, lower alkyl, lower alkoxy or chlorine, X denotes a vinyl, .beta.-sulfatoethyl,.beta.-thiosulfatoethyl or .beta.-chloroethyl group and Y is a chlorine, fluorine or bromine atom or a sulfo, hydroxyl, aliphatic or aromatic ether group or thioether group or a primary, secondary or tertiary amino group. These disazo compounds have fiber-reactive dyestuff properties and produce on hydroxyl- and/or carboxamide-containing material, in particular fiber material, such as cellulosic fibers, strong dyeings having good fastness properties.

Water-soluble disazo compounds containing substituted triazinyl radical,

Water-soluble disazo compounds having fiber-reactive dyestuff properties of the general formula (1) ##STR1## in which D.sub.1 and D.sub.2 are identical or different and each represents a phenyl radical or a naphthyl radical, both of which are substituted by a group of the formula moiety Y or formula moiety Z defined below and can additionally be substituted by one or two substituents from the group comprising sulfo, chlorine, bromine, lower alkyl and lower alkoxy, Z is a group of the formula (2a), (2b), (2c), (2d), (2e) or (2f) ##STR2## in which R denotes an alkyl group having 1 to 4 C atoms and X denotes a chlorine atom, the acetoxy group, the thiosulfate group, the phosphate group or the sulfato group; Y is a radical of the formula (3) ##STR3## in which R.sup.1 and R.sup.2 are identical to or different from one another and each denotes hydrogen or alkyl having 1 to 4 C atoms, and A is hydrogen or an optionally substituted alkyl group having 1 to 6 C atoms or a radical of the formula (4)

Water-soluble disazo compounds of 1-amino-8-naphthal-3,6- or

Water-soluble disazo dyestuffs of the formula ##STR1## which contain a 1-amino-8-naphthol-3,6- or -4,6-disulfonic acid moiety as a bivalent coupling component and which contain diazo components with fibre-reactive groups characterized by the inclusion of one or two chloro-triazinyl groups and one or two of the six groups defined by the substituent Z, namely, ##STR2## each of which are connected to the benzene moiety of the diazo component; the chloro-triazinyl group is further substituted by a substituted or unsubstituted phenylamino or substituted or unsubstituted naphthylamino group, a substitutent of which may be one of the six groups defined by the Z substituent; if there is only one chloro-triazinyl group in the compound, then the diazo component is also substituted by one of the Z substituents; these compounds are dyestuffs which exhibit a good fixation degree of the dyestuffs in fabrics.

Water-soluble disazo compounds containing an amino naphthol-disulfonic

Disazo compounds corresponding to the general formula (1) ##STR1## as well as their metal salts, in which D.sub.1 denotes the benzene or naphthalene nucleus, which can be further substituted by one or two substituents from the group of fluorine, chlorine, bromine, carboxy, lower alkyl, lower alkoxy and nitro and/or one, two or three sulfo groups, D.sub.2 is the benzene or naphthalene nucleus, which is substituted by the substituent X defined below and, in addition to the group --SO.sub.2 --Y, can be further substituted by one or two substituents from the group of carboxy, lower alkyl and lower alkoxy and/or by one substituent from the group of fluorine, chlorine, bromine and nitro and/or one, two or three sulfo groups, X denotes a fluorine, chlorine or bromine atom, which is necessarily bonded to D.sub.2 in ortho-position to the azo group, Y denotes the vinyl, .beta.-sulfatoethyl, .beta.-chloroethyl, .beta.-thiosulfatoethyl or a .beta.-acyloxyethyl group with the acyl radical of a lower alkanecarboxylic acid or of a benzoic acid or of a benzenesulfonic acid, and a and b each represent the number zero or 1, the sum of (a+b) being equal to 1 or 2. These compounds (1) are very suitable as fiber-reactive dyes for dyeing, for example natural or regenerated cellulose fiber, wool or synthetic polyamide fibers. They give on these materials intense dyeings and prints of good fastness properties, and are distinguished, in particular, by a good stability to copper ions, when used in printing processes.

Water-soluble azo compounds, a process for their preparation and their

The novel water-soluble disazo dyestuffs consist of two monoazo dyestuff moieties each containing as diazo component an amine of the benzene or naphthalene series and as coupling component an amino-naphthol-mono- or disulfonic acid. The two moieties are bonded to each other via a triazine radical which carries a halogen atom, and is bound to the amino groups of the coupling components and the diazo components contain a fiber-reactive radical of the vinyl sulfone series. To produce the dyestuffs 2 mols of the diazo compound carrying the fiber-reactive radical of the vinyl sulfone series is coupled with 1 mol of a bivalent coupling component consisting of 2 radicals of the aminonaphthol bound to the triazine ring via the amino groups, or two monoazo dyestuffs each synthesized from the aforesaid diazo component and an aminonaphthol-disulfonic acid coupling component are reacted with a 1,3,5-trihalogeno-triazine. The metal-free dyestuffs can be transformed into the corresponding heavy metal complex dyestuffs, preferably copper, cobalt and chromium complex dyestuffs, by treatment with an agent donating a heavy metal cation. The novel dyestuffs are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by clear shades, high tinctorial strength, a very good uptake from a long liquor and a good color-build up. The dyeings obtained therewith have a high fastness to processing and in use.

Water-soluble metal free or copper

Water-soluble compounds and their salts suitable as dyestuffs of the formula ##STR1## in which D is a benzene or naphthalene nucleus, R.sub.1 and R.sub.2 are, inter alia, hydrogen, halogen, lower alkyl, lower alkoxy and sulfo, R.sub.1 being in ortho-position to the azo group, X is a fiber-reactive radical of the vinyl sulfone series, K.sub.1 and K.sub.2 are radicals of coupling components of the acetoacetarylide and pyrozolone series and K.sub.2 additionally denotes a radical of the sulfonaphthol series, the coupling components being bound to the triazine ring via amino groups, Y is a halogen atom, a sulfo group, a thio ether or oxygen ether radical, or a primary, secondary or tertiary amino group, A is an aliphatic, aliphatic-heterocyclic, aliphatic-aromatic or aromatic bridge member and n is zero or one. The novel compounds are prepared, for example, by reacting 2 mols of the diazo component with the fiber-reactive radical of the vinyl sulfone series with 1 mol of a bivalent coupling component containing the two radicals K.sub.1 and K.sub.2 linked to each other by the triazine ring, or 2 triazine radicals linked with each other by bridge member A; or by reacting one mol each of a monoazo compound consisting of the said diazo component with the fiber reactive radical and a coupling component K.sub.1 or K.sub.2 with a corresponding triazine radical additionally carrying a halogen atom capable of reacting with the amino group. The metal-free compounds can be transformed into the corresponding heavy metal complex, preferably copper, cobalt and chromium complex compounds, by treatment with an agent donating a heavy metal cation. The novel compounds are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by high tinctorial strength, a very good uptake from a long liquor, a good color-build up. The dyeings and prints obtained therewith have a high fastness to processing and in use.

Water-soluble azo dyestuffs

New copper-complex formazan compounds of the general formula: ##STR1## in which A is a phenylene or naphthylene radical which can be substituted by halogen, nitro, lower alkyl, lower alkoxy, lower alkylsulfonyl, phenylsulfonyl and optionally alkylated sulfonamide groups and can also be substituted by the radical Z, defined below, B is a straight-chain or branched-chain alkyl group or alkenyl group, which can be substituted by an optionally substituted phenyl radical, or is a phenyl or naphthyl radical, which can be substituted by halogen, lower alkyl, lower alkoxy and lower carbalkoxy, or is the radical or a furan, thiophene, pyrrole, imidazole, indole, pyrazole, pyridine, pyrimidine, quinoline or benzimidazole, it being possible for B likewise to be substituted by the group Z, defined below, Z denotes a group which confers solubility in water, such as the carboxyl group or sulfo group, one to three of which are bonded to A and/or B, Cu is a copper atom, X denotes an oxygen atom or a carbonyloxy group and is bonded to A in the ortho-position relative to the nitrogen atom, Y represents the vinyl or .beta.-thiosulfatoethyl group and M denotes a hydrogen atom or the equivalent of a metal. The new copper-complex formazan compounds can be prepared in a manner which is in itself customary, for example by reacting an aromatic hydrazone compound of the general formula: ##STR2## in which A, B, X and Z have the abovementioned meaning, with the diazonium compound of an aromatic amine of the general formula: ##STR3## in which M and Y have the abovementioned meaning, and with an agent which donates copper. The new copper-complex formazan compounds have valuable dyestuff properties and are particularly suitable as fiber-reactive dye-stuffs for dyeing, for example, cellulose fiber materials, wool and synthetic polyamide fibers, on which they give strong reddish-tinged to greenish-tinged blue or clear blue dyeings with good fastness to light and wet processing.

Copper formazan compounds, processes for their preparation and their use

This invention relates to novel copper complex formazan compounds of the formula ##STR1## in which M is hydrogen or the equivalent of a metal and R is hydrogen or chlorine. The invention also relates to a process for their manufacture. The compounds can be used as dyestuffs, in particular fiber reactive dyestuffs for dyeing cellulose fiber materials, wool, or synthetic polyamide fiber materials for example, on which they exhibit intense blue dyeings having good fastness properties.

Copper complex formazan compounds, process for their manufacture and

An improved and novel process had been found for the esterification of aminophenol, amino-benzanilide and pyrazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide which improvement is characterized by that the esterification is performed in a machine which is operating with a kneading action and effect, using per mol .beta.-hydroxyethylsulfonyl compound 1 to 2.5 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which could charge the waste water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are prepared by this novel process in higher yields, in a higher degree of esterification rate and in a higher purity. They are obtained in form of a powder or plastic mass from the kneading machine, which is well transportable and storable, and can advantageously used in the form of this consistency, without intermediate isolation of the pure .beta.-sulfato compound itself, directly for the preparation of azo dyestuffs which are poor of inert salts, possess a high tinctorial strength and purity.

Process for the preparation of sulfuric acid semiester ethylsulfonyl

The novel water-soluble disazo dyestuffs consist of two monoazo dyestuff moieties each containing as diazo component an amine of the benzene or naphthalene series and as coupling component an amino-naphthol-mono- or disulfonic acid. The two moieties are bonded to each other via a bridge member bound to the amino groups of the coupling components and comprising two triazine radicals each containing a halogen atom, a sulfonic acid group or a thio ether or oxygen ether group or an amino group and the diazo components contain a fiber-reactive radical of the vinyl sulfone series. The metal-free dyestuffs can be transformed into the corresponding heavy metal complex dyestuffs, preferably copper, cobalt and chromium complex dyestuffs, by treatment with an agent donating a heavy metal cation. The novel dyestuffs are excellently suitable for dyeing and printing fiber material of natural and regenerated cellulose and natural, regenerated and synthetic polyamides. They are distinguished by a high tinctorial strength, a very good uptake from a long liquor, a good color- build up and good printing properties. The dyeings obtained therewith have a high fastness to processing and in use.

Water-soluble disazo dyestuffs

Improved process for the sulfatation of the hydroxy group of a .beta.-hydroxy-ethylsulfonyl group present in compounds selected from the dyestuff class which comprises carrying out the reaction in a machine operating with a kneading action and effect and with the use of only 1 to 5 times the equimolar amount of a concentrated sulfuric acid, of oleum or sulfur dioxide itself. The .beta.-sulfatoethylsulfonyl group containing dyestuffs, thus prepared have a high purity and are obtained in a high yield and esterification rate. Above all, the novel process is distinguished by a highly reduced salt and acid content of the waste water.

Process for the production of sulfuric acid semiester compounds by

A process for the dyeing or printing of a hydrophobic organic fibrous material containing or consisting of polyester, wherein

Process for the dyeing and printing of hydrophobic synthetic organic

Water-soluble dyestuffs are described which in the acid form possess the formula ##STR1## wherein D is a benzene or naphthalene nucleus, R.sub.1 is linked to D in ortho-position to the azo group and means hydrogen, halogen, lower alkoxy, lower alkyl, carboxy or sulfo, R.sub.2 is hydrogen, halogen, lower alkyl, lower alkoxy or sulfo and X is the vinyl group or a sulfato-, chloro- or thiosulfatoethyl group, A is a bridging member preferably selected from the diphenylene, diphenylsulfone and diphenylamine series, Z and Z.sup.1 each represent a hydroxy or amino group with the proviso that each Z and each Z.sup.1 have the same meaning. These novel dyestuffs are prepared by diazotization and coupling of the corresponding diazo and coupling components in usual manner known in the art. The novel dyestuffs possess a very valuable fiber-reactivity and are suitable for dyeing natural and regenerated cellulose or natural, regenerated or synthetic polyamide fiber materials. They can easily be applied and fixed by application methods usual and known in the art, and yield on these fiber materials dyeings and prints which possess good fastnesses, especially fastnesses to light, to washing, to perspiration and to cross-dyeing. Their fixation degree on the fiber material and correspondingly their tinctorial strength are outstanding.

Water-soluble dyestuffs, processes for their manufacture, their use as

An improved and novel process has been found for the esterification of amino-benzoxazolone compounds containing a .beta.-hydroxyethylsulfonyl group, by means of sulfuric acid or sulfur trioxide, with simultaneous or subsequent hydrolytic cleavage of the oxazolone ring, wherein the esterification and optional hydrolytic ring cleavage are performed in a machine which is operating with a kneading action and effect, using per mol of .beta.-hydroxyethylsulfonyl compound 1 to 20 times the equivalent molar amount of concentrated sulfuric acid, oleum or sulfur trioxide. This novel process has the great advantage that great amounts of sulfuric acid are saved which would contaminate the waste-water, also in form of sodium sulfate formed after the required neutralization. Furthermore, the .beta.-sulfatoethylsulfonyl compounds formed as end-products in the esterification process are obtained in higher yields, in a higher esterification rate and in a higher purity. They may be obtained in form of a powder or plastic mass, which is conveniently transportable and storable, and can advantageously be used, if ring cleavage had taken place, without intermediate isolation of the pure sulfato compound itself, directly for the preparation of azo dyestuffs which are low in content of inert salts and possess a high tinctorial strength and purity.

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Frankfurt am Main, Germany

Ernst Hoyer