Hoechst Aktiengesellschaft

Clariant Corporation

Geohumus Gmbh

Heinrich Volk

Theodor Papenfuhs

Rudolf Neeb

Werner Wykypiel

Siegbert Rittner

Michael Meier

Helmold Von Plessen

Steffen Dapperheld

Klaus Forstinger

Wolfgang Ironich

Thomas Schach

Karl Peter

Theodor Papenfahs

Manfred Koch

Thomas Volk

The present invention relates to a process for preparing arylhydrazines of the formula R.sup.1 R.sup.2 R.sup.3 Ar--NH--NH.sub.2 (I) by reacting an arylhydrazinedisulfonate of the formula ##STR1## in which R.sup.1, R.sup.2, and R.sup.3 are identical or different and are H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen or OH, Ar is phenyl or naphthyl, M.sup.1 and M.sup.2 are identical or different and are H, NH.sub.4, an alkali metal or 1/2 alkaline earth metal and R.sup.1, R.sup.2, R.sup.3 and Ar in the formulae (I) and (II) have the same meaning, with water and an inorganic acid at from 0 to 100.degree. C. in the presence of an inert organic solvent to give the corresponding arylhydrazine salt and treating the arylhydrazine salt with a base.

Process for preparing arylhydrazines

The invention relates to a process for the preparation of 3-hydroxy-N-benzimidazolon-5-yl-2-naphthamide, which comprises reacting 5-aminobenzimidazolone and sodium carbonate in N-methylpyrrolidone with a solution of 3-hydroxy-2-naphthoyl chloride in xylene or toluene, filtering, washing with xylene or toluene, introducing the filter cake into water to which sodium carbonate has been added and steam-distilling, filtering off the residue with suction, washing and drying.

Process for the preparation of

The process for the preparation of 2(3H)-benzothiazolones which are optionally substituted on the benzene ring by reacting a 2-aminobenzothiazole which is optionally substituted on the benzene ring with a diazotization agent in the presence of aqueous hydrochloric acid, if appropriate with addition of a chloride, to give a diazonium chloride, reacting the diazonium chloride directly to give a 2-chlorobenzothiazole, which is optionally substituted on the benzene ring, and hydrolyzing the 2-chlorobenzothiazole, without intermediate isolation, at 120.degree.-200.degree. C. under reaction pressure.

Process for the preparation of 2(3H)-benzothiazolones

A process for the preparation of a 2-aminobenzothiazol of the formula ( I ) ##STR1## in which R.sub.1 and R.sub.2 independently of each other are hydrogen, fluorine, chlorine, bromine or iodine, trifluoromethyl or C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or nitro groups, by conversion of an arylthiourea of the formula (II) in which R.sub.1 and R.sub.2 have the meaning mentioned, which comprises carrying out the conversion in 99 to 100% strength of sulfuric acid with continuous addition of catalytic amounts of bromine, hydrogen bromide or bromide in the form of aqueous solutions and using an arylthiourea of the formula (II) which contains 1 to 35% water.

Process for the preparation of 2-aminobenzothiazoles

The invention relates to a process for purification of 2-hydroxynaphthalene-6-carboxylic acid by recrystallization. In this process, the crude acid is recrystallized from water-miscible linear or cyclic aliphatic ethers, aliphatic polyethers or aliphatic hydroxy ethers or from at least 10% strength by weight aqueous solutions of these ethers. Recrystallization from a 35-90% strength by weight aqueous solutions of 1,4-dioxane is particularly preferred.

Process for the purification of 2-hydroxynaphthalene-6-carboxylic acid

6-Hydroxy-2-naphthoic acid can be selectively acetylated to 6-acetoxy-2-naphthoic acid, in particular in the presence of admixtures of isomeric hydroxy-naphthoic acids, and thus be separated from those isomeric admixtures. The acetylation is affected in aqueous alkaline solution by reaction with acetic anhydride. By hydrolysis of the 6-acetoxy-2-naphthoic acid, a pure 6-hydroxy-2-naphthoic acid is obtained.

Process for preparing 6-acetoxy-2-naphthoic-acid and pure

A process for preparing pure alkyl 1-hydroxy-2-naphthoates of the formula ##STR1## in which R denotes lower alkyl, by adjusting, with mineral acid, to pH 5.5-6.5 an aqueous solution of monoalkali and/or dialkali metal salts of 1-hydroxy-2-naphthoic acid, then adding a surface-active compound (1) of the formula ##STR2## in which R, R.sub.1, R.sub.2 and R.sub.3 denote aliphatic radicals of 1-30 carbon atoms which are substituted and which can contain, in the terminal positions, ionic substituents, or hydroaromatic carbocyclic or cycloaliphatic radicals of 4-8 carbon atoms, and in which X.sup.(-) represents one equivalent of an inorganic or organic acid, or (2) of the formula ##STR3## in which R, R.sub.1, R.sub.2 and X.sup.(-) have the abovementioned meanings, the total number of the carbon atoms of R, R.sub.1 and R.sub.2 being at least 6 and 2 of the aliphatic radicals R, R.sub.1 and R.sub.2 being able to form, together with the sulfur atom, a heterocyclic ring, or (3) of the formula ##STR4## in which R, R.sub.1, R.sub.2, R.sub.3 and X.sup.(-) have the meanings given in the definition of the formula (II), the total number of the carbon atoms of R, R.sub.1, R.sub.2 and R.sub.3 being at least 8 and 2 or 3 of the aliphatic radicals R, R.sub.1, R.sub.2 and R.sub.3 being able to form, together with the phosphorus atom, a heterocyclic ring, in an amount of 0.5 to 5% by weight, relative to 1-hydroxy-2-naphthoic acid, separating off the precipitates at 50.degree. C.-100.degree. C., and esterifying the pure monoalkali metal 1-hydroxy-2-naphthoate present in aqueous solution with dialkyl sulfate at pH 5.5-6.5 between 30.degree. C. and 80.degree. C.

Process for preparing pure alkyl 1-hydroxy-2-naphthoates

In the carboxylation of 2-alkali metal naphtholates under pressure and at temperatures of above 200.degree. C., apart from the alkali metal salt of 2-naphthol-3-carboxylic acid and free 2-naphthol considerable amounts of resinous by-products are obtained which according to the hitherto known processes have to be separated and removed in a very expensive manner. According to this invention, the alkali-soluble acidic resins are separated from this carboxylation melt after its solution in water during the work-up of the carboxylation product by means of a cationic quaternary ammonium compound. These surface-active compounds precipitate the alkali-soluble acidic resins in such a manner that they can be easily removed from the alkali metal salts of 2-hydroxynaphthalene-3-carboxylic acid dissolved in water.

Process for separation of 2-hydroxynapthalene-3-carboxylic acid from the

New valuable, water-insoluble mixed diaminophenylenedisazomethine-naphthalene metal-complex compounds had been found consisting of two or more metal-complex disazomethine compounds of different constitution or different metal complexes which are prepared according to this invention by reacting one or several o-phenylene diamines with one or several hydroxy-naphthaldehydes at which process metallization is carried out by addition of one or several metal-yielding agents of one or several different metals before, during or after the condensation reaction of the amino and aldehyde compounds. The new mixed metal-complex compounds are suitable as colorants, especially as pigments for the coloring of printing pastes, printing inks, high-molecular plastic masses, lacquers, paints and spinning masses which colored materials possess very good fastness properties to, for example, light, to weather, to solvents or to migration, and the colorants themselves possess an excellent fastness to heat and have a high tinctorial strength, a good transparency, a good dispersability and, in general, pure shades.

Water-insoluble disazomethine mixed metal-complex compounds, process for

New metal-complex disazomethine compounds of the formulae ##STR1## WHEREIN R is a single bond, a straight-chained or branched alkylene radical which may be interrupted by one or more hetero atoms, such as 1, 2, 3 or 4 moieties selected from a group consisting of isocyclic and heterocyclic ring and other bivalent group, or is a cycloalkylene radical, an arylene or a heterocyclic radical, Z is a group capable of forming metal complexes, X is a carboxylic acid group, carboxylic acid ester group, an optionally substituted carboxylic acid amide or carboxylic acid hydrazide group and M is a bivalent metal atom, had been found which are very well suitable as colorants, especially as pigments, for example, for coloring plastic masses, paints, lacquers, for the use in spin-dyeing of viscose and cellulose acetate, for coloring printing pastes in graphic industry and paper masses, and have a high tinctorial strength, a good transparency, pure shades, excellent fastness to migration, to overvarnishing to light, to weather, to solvents and to heat, corresponding to the material colored with them.

Metal-containing disazomethine compounds, process for preparing them and

Novel 2-hydroxynaphthalene-1-aldehydes have been found which have the general formula (I) ##STR1## wherein R is a carboxylic acid group, a carboxylic acid ester group, preferably of an alkanol or of an optionally substituted phenol, an optionally substituted carboxylic acid amide group, or an optionally substituted carboxylic acid hydrazide group, which are very valuable intermediate products for the preparation of coloring agents, optical brighteners, textile auxiliary agents and pharmaceutical products.

Novel 2-hydroxynaphthalene-1-aldehydes, process for preparing them and

New water-insoluble compounds have been found of the formula ##STR1## wherein n is 1, 2 or 3, each R, different or the same, is halogen, lower alkyl, lower alkoxy, phenoxy, phenoxy substituted by halogen, lower alkyl or lower alkoxy, or is hydroxy, cyano, trifluoromethyl, carboxy, lower carbalkoxy or lower alkanoyl or benzoyl or benzoyl substituted by halogen, lower alkyl or lower alkoxy, and Z is hydrogen, halogen, lower alkoxy, nitro or cyano, which are well suitable as pigments for dyeing polymer masses, lacquers, caoutchouc, synthetic leather or spin-dyeing viscose or cellulose acetate, for paper and printing pastes. The dyeings obtained with them are excellently fast to light, weather and organic solvents and to the action of heat and are distinguished by a high tinctorial strength, good transparency and very clear shades.

Water-insoluble nickel-complex disazo methine compounds

New valuable metal complex disazomethine compounds of the formula ##STR1## had been found wherein R is hydrogen, an alkyl, aralkyl, cycloalkyl, aryl or heterocyclic radical, an amino group which may be substituted by alkyl or aryl radicals, or a guanidino group, X stands for a -CO- or -SO.sub.2 -group, Y stands for hydrogen, a halogen atom, an alkyl, alkoxy or nitro group, R.sub.1 stands for hydrogen or an alkyl radical, Z stands for hydrogen, a halogen atom, an alkoxy or nitro group and M is a bivalent metal atom. The new compounds are very well suitable as dyes, especially good pigments, and can be used, for example for the dyeing of masses of synthetic materials, for pigmenting paints and lacquers, for spin-dyeing viscose and cellulose acetate and for pigmenting polyethylene or similar polymers, caoutchouc or synthetic leather. Their dyeings have excellent fastnesses as, for example, to migration, light, weather and solvents. Furthermore, the compounds themselves have an excellent heat stability, a high color intensity and high degree of purity of the shades.

Growing community of inventors

Bad Vilbel, Germany

Heinrich Volk