Hoechst Aktiengesellschaft

Hermann Fuchs

Fritz Meininger

Klaus Filzinger

Gustav Kapaun

Peter Mischke

Walter Gilb

Hans-Tobias Macholdt

Otto Arndt

Hermann-Heinz Konrad

Theodor Papenfuhs

Hartmut Springer

Gunther Schwaiger

Hanspeter Gethoffer

Jorg Gitzel

Rudiger Baur

Folker Kohlhaas

Werner Brodt

R Udiger Baur

Wilfried Theiss

Wilfried Theisse

J Org Gitzel

Tetraphenylborates are obtained in an industrially advantageous grade by spray drying an organic, aqueous or organic-aqueous extract of the tetraphenylborates obtainable in the tetraphenylborates synthesis. It is advantageous to treat the specified extract prior to spray drying with pH-controlling auxiliaries and adsorbents to remove byproducts or to limit their formation. The process gives tetraphenylborates in a homogeneous technical grade, i.e. in a narrow particle size distribution and in a particular particle shape, which improves the dispersibility in the medium to be used.

Process for isolating tetraphenylborates

Tetraphenylborates are obtained in an industrially advantageous grade by spray drying an organic, aqueous or organic-aqueous extract of the tetraphenylborate obtainable in the tetraphenylborate synthesis. It is advantageous to treat the specified extract prior to spray drying with pH-controlling auxiliaries and adsorbents to remove byproducts or to limit their formation. The process gives tetraphenylborates in a homogeneous technical grade, i.e. in a narrow particle size distribution and in a particular particle shape, which improves the dispersibility in the medium to be used.

An ecologically and economically improved process for the preparation of 2,5-di-phenylamino-terephthalic acid and its di-alkyl esters of the formula (1) ##STR1## in which R is a hydrogen atom or a methyl group and R' is a hydrogen atom or a methyl or ethyl group.

Process of the preparation of 2,5-di-phenylamino-terephthalic acid and

A process for the preparation of 2,5-di(phenylamino)terephthalic acid and its dialkyl esters of formula (I): ##STR1## in which R is a hydrogen atom or a methyl group and R' is a hydrogen atom or a methyl or ethyl group.

Process for the preparation of 2,5-di(phenylamino)-terephthalic acid and

A process for the continuous preparation of imidoperoxycarboxylic acids of the formula ##STR1## in which A is C.sub.2 -C.sub.4 -alkylene, phenylene, naphthylene or a group of the formula ##STR2## and R is a group of the formula --COOH, --SO.sub.3 H or --Cl, and X is C.sub.1 -C.sub.19 -alkylene or arylene, in which a solution of imidocarboxylic acids of the formula ##STR3## in sulfuric acid or methanesulfonic acid and an aqueous solution of hydrogen peroxide are continuously metered into a static mixer, then the solution of the imidoperoxycarboxylic acid obtained in this way is treated with water and the precipitated product is isolated.

Process for the continuous preparation of imidoperoxycarboxylic acids

Compounds of the formula (1) ##STR1## in which X denotes a sulfur atom or the group ##STR2## in which R denotes a hydrogen atom, an alkylene-C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.6 - or alkyl-C.sub.1 -C.sub.6 - group, each of which can be substituted by hydroxyl, sulfo, carboxyl or cyano groups, R.sub.1 denotes a hydrogen atom or an alkyl-C.sub.1 -C.sub.6 -group which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), hydroxyl, amino, methylamino, acetylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino, methoxy, ethoxy, .beta.-hydroxyethylsulfonyl, phenyl, monosulfophenyl, disulfophenyl, or 4-[.beta.-hydroxyethylsulfonyl]-2-sulfophenyl groups, or represents a phenyl or naphthyl group, each of which can be substituted by --SO.sub.3 M or COOM groups (where M denotes an H, Li, Na, K or Ca atom), alkyl-C.sub.1 -C.sub.4 -, alkoxy-C.sub.1 -C.sub.4 -, amino, methylamino, alkyl-C.sub.1 -C.sub.4 -sulfonylamino or acetylamino groups, and R.sub.2 is hydrogen or oxygen, and process for their preparation by reacting compounds of the formula (2) ##STR3## in which Y denotes a chlorine or bromine atom, with a compound of the formula (3)

Substituted phenyl hydroxyethyl sulfones, and process for their

Triphendioxazine compounds, which are suitable as fiber-reactive dyestuffs, of the general formula (1) ##STR1## in which R.sup.1 and R.sup.2 are each a hydrogen atom, an optionally substituted alkyl group with 1 to 8 carbon atoms, the substituents being, for example, sulfo, sulfato, carboxy and optionally substituted alkylamino and dialkylamino groups, or a cycloalkyl group which can optionally be substituted by methyl and/or amino, alkanoylamino or benzoylamino, or an optionally substituted phenyl radical, the substituents of which are, for example, sulfo, carboxy, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, nitro and .beta.-sulfatoethylsulfonyl, or a naphthyl radical which can be substituted by 1, 2 or 3 sulfo groups and/or a fiber-reactive group of the vinylsulfone series, or in which R.sup.1 and R.sup.2, together with the nitrogen atom, can form a heterocyclic radical, and in which the benzene nuclei A can be substituted by 1 or 2 substituents from the group comprising alkyl with 1 to 6 carbon atoms, alkoxy with 1 to 5 carbon atoms, halogen, carboxyl and sulfo, the two radicals X.sup.1 and X.sup.2 are identical to one another or different from one another and are a hydrogen atom, a halogen atom, a cycloalkyl group, an aralkoxy group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, an aralkyl group or a cyano, carboxy, carbalkoxy, mono- or di-alkylcarbamoyl, arylarylcarbamoyl, alkanoylamino or aroylamino group, and Y represents the vinyl group or ethyl group which contains, in the .beta.-position, a substituent which can be eliminated by an alkali, or is the .beta.-hydroxyethyl group, and M represents a hydrogen atom or an alkali metal or the equivalent of an alkaline earth metal, and the compound (1) contains at least one sulfo or sulfato group. The compounds (1) are used for dyeing material containing hydroxy and/or carboxamide groups, in particular fiber material, such as cellulose fiber material and wool, on which they give deep blue dyeings.

Water-soluble triphendioxazine compounds

A water-soluble azo compund of formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z in which Z is chlorine, bromine, fluorine, lower alkanoyloxy, benzoyloxy, sulfobenzoyloxy, benzenesulfonyloxy, toluenesulfonyloxy, lower alkylsulfonylamino, arylsulfonylamino, phenoxy, dialkylamino, each alkyl being of from 1 to 4 carbon atoms, thiosulfato, phosphato or sulfato;

Water-soluble monoazo compounds containing a N-(sulfoalkyl)-aniline

Water-soluble fiber-reactive phthalocyanine compounds of the general formula (1) ##STR1## in which Pc denotes the radical of metal-free or metal-containing phthalocyanine, with the sulfonic acid or sulfonamide groups being bonded in the 3-positions of the aromatic rings of the phthalocyanine, R.sub.1 and R.sub.2 each denote a hydrogen atom or an alkyl group of 1-6 carbon atoms and which can be substituted by methoxy, ethoxy, propoxy, C.sub.2 H.sub.5 --O--C.sub.2 H.sub.4 --O--, cyano, acetylamino, carboxyl, HO.sub.3 S--, H.sub.2 O.sub.3 P--, phenyl, methylphenyl, methoxyphenyl, dimethylamino, diethylamino, .beta.-hydroxyethylamino, .beta.-hydroxyethoxy, N-phenylureido, N-alkyl.sub.C.sbsb.1.sub.-C.sbsb.4 ureido or N-cycloalkylureido groups or an allyl, 2-methallyl, crotyl or cycloalkyl group, and R.sub.1 and R.sub.2, together with the nitrogen atom, can represent the radical of a heterocyclic saturated or unsaturated ring, or R.sub.1 and R.sub.2 represent a phenyl radical which can be substituted by methyl, ethyl, methoxy, ethoxy, carboxyl or sulfonic acid groups, R.sub.3 denotes a hydrogen atom or an alkyl group of 1 to 4 carbon atoms and which can be substituted by hydroxyl or carboxyl groups, X represents a hydrogen atom or an alkyl or alkoxy group of 1 to 4 carbon atoms, Y represents the vinyl group or the grouping of the formula --CH.sub.2 --CH.sub.2 --Z in which Z denotes an inorganic or organic radical which can be eliminated under alkaline conditions, a represents a number between 0 and 2, b represents a number between 0 and 2 and c represents a number between 1.7 and 2.6, with the proviso that the sum of a, b and c is at most 4, a process for their preparation, and their use for dyeing wool, silk, polyamide fibers, leather or materials containing hydroxyl groups.

Water-soluble fibre-reactive phthalocyanine compounds

Water-soluble disazo compounds of the formula (1) ##STR1## and diamino compounds serving as starting compounds (tetrazo components), of the formula (4) ##STR2## in which the formulae moieties occurring twice, namely Z, K and X, in each case have a meaning identical to one another and the groups Z are bonded to the two benzene nuclei in each case in the ortho- or in each case in the para-position relative to the ethylenedioxy substituent, and the azo groups or amino groups and the groups Z in the benzene nuclei are in each case bonded in the meta-position relative to one another and K is the radical of a coupling component containing a sulfato, carboxy or sulfo group, X denotes a hydrogen atom or a fiber-reactive group and Z is a group of the formula --SO.sub.2 --CH.dbd.CH.sub.2 or --SO.sub.2 --CH.sub.2 --CH.sub.2 --Y in which Y denotes a radical which can be eliminated in aqueous medium under alkaline or acidic conditions or the hydroxy group. Disazo compounds of the formula (1) can be used as dyestuffs having fiber-reactive properties for dyeing, for example, cellulose fiber material and wool and be prepared by tetrazotizing diamines of the formula (4) and coupling with coupling components evident from the formula (1). Diamino compounds of the formula (4) are obtained by acetylating a 1,2-di-(o- or p-aminophenoxy)-ethane, chlorosulfonating this bis-acetylamino compound and reducing the sulfonyl chloride groups to sulfinic acid groups, which are then oxyethylated to give .beta.-hydroxyethylsulfonyl groups, which, after deacetylation of acetylamino groups, can be converted in a manner which is in itself known into one of the abovementioned groups Z, for example into the .beta.-sulfatoethylsulfonyl group by means of a sulfating agent.

Water-soluble disazo compounds and new bis-(aminophenoxy)-ethane

Water-soluble disazo compounds, which can be used as fiber reactive dyestuffs and correspond to the general formula ##STR1## in which Y is vinyl or --CH.sub.2 --CH.sub.2 --Z, Z being sulfato, phosphato, halogen or hydroxy;

Water-soluble disazo compounds suitable as fiber-reactive dyestuffs

New water-soluble anthraquinone-azo compounds of the general formula ##STR1## and their salts; in this formula the R.sub.1 s both are sulfo groups, or one of the two is a hydrogen atom and the other is a sulfo group, R is hydrogen or lower alkyl and D, as the radical of a diazo component, is the benzene or naphthalene nucleus, which is monosubstituted or disubstituted by a fiber-reactive group Z, corresponding to the index n being 1 or 2, and which furthermore can be substituted by 1 to 3 substituents selected from lower alkyl, lower alkoxy, halogen, nitro and sulfo. The new azo compounds are very suitable as dyestuffs for dyeing fiber materials containing hydroxy groups or carbonamide groups, such as natural or synthetic polyamide fibers or polyurethane fibers and cellulose fibers, yielding deep dyeing and prints with very good fastness properties to wet processing and very good fastness properties to light. The new compounds of the above formula are obtained by diazotizing a 1-amino-2-sulfo-4-(4'-aminophenyl)-aminoanthraquinone compound, which is substituted by sulfo in the 2'- and/or 5'-position, by means of an equivalent amount of sodium nitrite in the presence of a mineral acid, coupling this diazonium salt with an acetylsuccinic acid ester of a lower alkanol, cyclizing this radical of the coupling component to the pyrazolone ring and coupling the pyrazolono-phenylamino-anthraquinone compound, thus obtained, with a diazonium compound of an amine of the formula

1-Amino-2-sulfo-(4'-pyrazolonyl-phenyl)-aminoanthraquinone compounds and

New compounds had been found which correspond to the formula ##STR1## as well as processes for preparing them by sulfonation of 3.beta.-sulfato- or 3-.beta.-hydroxyethylsulfonyl - aminobenzene. The novel compounds are valuable intermediary products for the preparation of azo fibre-reactive dyestuffs which have very good dyeing properties and a high fibre-reactivity yielding dyeings of excellent fastnesses, especially to light and wet processing.

Process for the preparation of

Water-soluble disazodyestuffs of the formula ##STR1## in which R.sub.1 and R.sub.2 are identical or different and each is hydrogen, methyl, ethyl or methoxy, and R.sub.3 is hydrogen, chlorine, nitro or alkyl of 1 to 4 carbon atoms, and their salts have been found which possess very good dyeing characteristics and are very well suitable for dyeing of synthetic polyamides and yield dyeings on these fibers with good to very good wet fastnesses and fastnesses to processing and to use. In accordance with this, an improved process had been found for coloring synthetic polyamide fibres by applying the above dyestuffs of the invention on said fibres in usual dyeing and printing methods and fixing them on the fibre by methods as usual in the art.

Water-soluble disazo dyestuffs and process for coloring synthetic

Novel, valuable unsymmetrical 1:2-cobalt complex dyestuffs of an azo compound and an azomethine compound have been found which are well suited for the dyeing of natural and synthetic polyamide fibres, yielding even dyeings of high fastnesses to wet processing and use as well as to light. The novel dyestuffs can be prepared either by cobalting the equimolar mixture of the metalfree azo and azomethine dyestuffs with a cobalt-yielding compound at a pH of 5 to 10 at 60 .degree. to 150.degree. C., or by first cobalting the azomethine compound and then reacting it with the equimolar amount of the metalfree azo compound. The compounds are 1:2-cobalt complex compounds of the compounds ##STR1## in which R.sub.1 is chlorine, lower alkyl or nitro, R.sub.2 is hydrogen, lower alkyl or lower alkoxy, R.sub.3 is hydrogen, chlorine, nitro or lower alkyl, Z is ##STR2## in which R.sub.4 is hydrogen, lower alkyl or lowr alkoxy, R.sub.5 is hydrogen, lower alkyl or lower alkoxy, X is hydroxy, sulfoalkyl of from 1 to 4 carbon atoms, or ##STR3## R.sub.9 is hydrogen or lower alkyl, and R.sub.6 and R.sub.7 are different from each other and each is nitro or sulfo.

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Konigstein/Taunus, Germany

Hermann Fuchs