Hoechst Aktiengesellschaft

Cassella Aktiengesellschaft

Farbwerke Hoechst Aktiengesellschaft

Klaus Hunger

Wolfgang Rieper

Heinrich Frolich

Joachim Ribka

Hartmut Springer

Fritz Meininger

Manfred Pesenacker

Friedrich Wilhelm Weingarten

Theodor Papenfuhs

Hasso Hertel

Josef Landler

Erhard Worfel

Ernst Klappert

Dieter Weber

Wolfgang Bauer

Bernhard Mees

Otto Fuchs

Kurt C Habig

Reinhard Zunker

Hans-Joachim Lenz

Edwin Baier

Konrad Lohe

The invention relates to 4,4'-diaminodiphenyl compounds of the formula I ##STR1## in which X denotes the n-propyl, isopropyl, n-butyl, isobutyl, 1-methylpropyl, n-propoxy, isopropoxy, isobutoxy, 1-methylpropoxy or 2-methoxyethoxy radical and A is 0 or the equivalent of an inorganic acid. The preparation is effected by reducing ortho-X-substituted nitrobenzene and benzidine rearrangement of the resulting hydrazobenzene derivative. The compounds of the formula (I) are suitable for use as components in the preparation of dyes and pigments.

4,4'-diaminodiphenyl compounds, process for their preparation and their

Bisdiazonium salts of the formula (1) ##STR1## in which R denotes a linear or branched alkyl or alkoxyalkyl radical having 3-5 carbon atoms and X.sup.- represents the radical of a strong acid or of a zinc chloride double salt, and a process for their preparation by diazotizing a 4,4'-diamino-3,3'-dialkoxybiphenyl of the formula (2) ##STR2## in which R has the meaning mentioned, in an aqueous, strong, non-oxidizing inorganic or organic acid at temperatures from about -10.degree. C. to about +40.degree. C. by means of an alkali metal nitrite, and precipitating the resulting bisdiazonium salts by adding an alkali metal chloride, bisulfate, monosulfonate of 1,5-naphthalenedisulfonic acid or tetrafluoroborate or zinc chloride. These salts are useful in dyeing and printing textile fiber materials by the methods of the ice color technique, using suitable coupling components; they are also useful for preparing photographic tracings by the methods of reprography.

Bisdiazonium salts of 4,4'-diamino-3,3'-dialkoxybiphenyls and a process

Coloring natural or synthetic fiber material containing hydroxyls or nitrogen is achieved by printing or dyeing the fiber material with a water-soluble disazo dyestuff of the formula ##STR1## wherein R.sup.1 is alkyl, alkoxy or alkoxyethoxy, each having 3-6 carbon atoms, B.sup.1 is the radical of a 1-amino-8-hydroxynaphthalene monosulphonic or disulphonic acid and B.sup.2 is the same as B.sup.1 or another napthyl moiety.

Water-soluble aminonaphthol disazo dyestuffs, their preparation and

An improved process for the manufacture of a monoazo acetoacetylaminobenzimidazolone pigment of the formula ##STR1## by coupling the components in an aqueous medium in the presence of an oxethylation product of an alcohol or alcohol mixture having from 8 to 14 carbon atoms and 3 to 10 mols of ethylene oxide, and heating the aqueous pigment suspension after complete coupling. The pigment thus obtained avoids an after-treatment in anhydrous organic solvents and has good tinctorial strength, high hiding power and good properties with respect to flow and dispersibility.

Process for the manufacture of a monoazo acetoacetylaminobenzimidazolone

Process for improving the application properties of disazo pigments obtained by coupling bis-diazotized chlorine-substituted 4,4'-diaminobiphenyls with acetoacetylaminobenzenes, which includes adding sulfite ions to the pigment suspension obtained in the coupling and then heating for one half to two hours at 50.degree. to 100.degree. C. The process produces, above all in large scale industrial batches, a product of uniform quality and having acceptable fastness to solvents, overlacquering, migration and bleeding.

Process for improving the application properties of disazo pigments

Using the method of azoic dyeing, fast blue dyeings are obtained when the bis-diazotable diazo component used is a compound of the general formula (1) ##STR1## in which R is a straight-chain or branched alkyl group of 3 to 5 carbon atoms or a (C.sub.1 -C.sub.3)-alkoxy-(C.sub.2 -C.sub.4)-alkyl group having straight-chain and/or branched alkyl groups of in total 3 to 5 carbon atoms, and the coupling component used is a compound conforming to the general formula (2) ##STR2## in which Z stands for a hydrogen atom or a halogen atom or an alkoxy group of 1 to 4 carbon atoms and Aryl denotes a phenyl radical or a 1-naphthyl radical which can be substituted by 1, 2 or 3 substituents from the group consisting of halogen, nitro, alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, and the coupling reaction and dye formation on the fiber are carried out at a pH value between 4 and 10.

Process for preparing water-insoluble blue azo dyes on the fiber:

Disazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A.sup.1 and A.sup.2, independently of each other, represent hydrogen, methyl or ethyl and Z.sup.1 and Z.sup.2 in the 6- or 7-position of the heteroaromatic ring system, independently of each other, represent hydrogen, bromine, chlorine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro, are obtained by coupling a monodiazotized p-diaminobenzene substituted by X and Y analogously to the formula I with a 5-acetoacetylaminobenzimidazolone which carries the radicals A.sup.1 and Z.sup.2 analogously to the formula I, and reacting the resulting aminoazo compound after another diazotization with a 5-acetoacetylaminobenzimidazolone which carries the radicals A.sup.2 and Z.sup.2 analogously to the formula I, to give the disazo compound of the formula I. The crude product is subsequently thermally aftertreated at 80.degree. to 200.degree. C. In the case where X, Y or Z.sup.1 does not denote a nitro group, it is possible to use as an alternative to the p-diaminobenzene derivative a corresponding p-aminonitrobenzene derivative. In this case, analogous diazotization and coupling is followed by reduction of the resulting nitroazo compound to the aminoazo compound, which is converted into the compound of the formula I as described above. The symmetrical or asymmetrical disazo compounds of the formula (I) are obtained in a particle size of .ltoreq.0.25 .mu.m and are suitable for use as pigments in printing inks, lakes and emulsion paints, for coloring plastics, rubber, natural and synthetic resins or spinning compositions and for pigment printing on, for example, textile fiber materials and paper. The pigments are tinctorially very strong and have very high solvent, migration, light and weathering fastness properties and a high thermostability.

Disazo compounds derived from acetoacetylamino-benzimidazol-2-ones

The invention relates to aminoazo compounds of the formula I ##STR1## in which X and Y are identical or different and denote hydrogen, chlorine, bromine, methyl, methoxy, ethoxy, nitro, trifluoromethyl, carbomethoxy or carboethoxy, A represents hydrogen, methyl or ethyl, and Z in the 6- or 7-position of the heteroaromatic ring system is hydrogen, chlorine or bromine, methyl, methoxy, ethoxy, carbomethoxy, carboethoxy or nitro. The compounds of the formula I are prepared by coupling a monodiazotized p-diaminobenzene substituted by X and Y analogously to the formula I with a 5-acetoacetylaminobenzimidazolone which carries the radicals A and Z analogously to the formula I. In the case where X, Y or Z does not denote a nitro group, it is possible to use in place of the p-diaminobenzene derivative a p-aminonitrobenzene derivative which is disubstituted by X and Y in the 2- and 5-positions. In this case, the product after diazotization and coupling is initially a nitro compound which can be converted by reduction into the aminoazo compound of the formula I. The aminoazo compounds are used as starting materials for preparing disazo compounds, preferably disazo pigments, through diazotization in conventional manner and coupling onto compounds which are capable of coupling, for example onto 5-acetoacetylaminobenzimidazolones. The disazo pigments are distinguished by high tinctorial strength, excellent fastness to solvents and migration, and high thermostability.

Amino compounds derived from 5-acetoacetylamino-benzimidazolones

Diaryl pigments having an excellent stability to heat are obtained by carrying out the coupling of bis-diazotized 3,3'-dichloro-4,4'-diaminobiphenyl with acetoacetanilides in the presence of an added quantity of acetoacetanilides which are monosubstituted or disubstituted in the 3-position or 4-position of the nucleus. As a result of their good heat stability, these pigments are particularly suitable for pigmenting plastics having processing temperatures above 200.degree. C.

Diaryl pigments with improved heat stability obtained by coupling

Azo pigments are obtained by diazotizing a diazotizable aromatic amine without solubilizing groups in anhydrous dipolar aprotic water-miscible solvents with the stoichiometric amount or a small excess of nitrosylsulfuric acid or nitrosyl chloride, coupling the diazonium compound so obtained with a coupling component and isolating the pigment obtained in usual manner. This process is carried out in homogeneous solution and yields azo pigments the advantageous properties of which cannot be achieved by other methods, for example, the excellent purity, grain softness, narrow range of particle size distribution, excellent dispersibility in plastic materials and color lacquers, high gloss and excellent opacity in color lacquers.

Azo pigments obtained by diazotizing in a dipolar aprotic organic solvent

The invention relates to a process for improving the application properties of Pigment Yellow 13. The crude pigment is heated in an aqueous suspension to temperatures above 100.degree. C. Pigment Yellow 13 thus obtained is particularly suitable for replacing lead-containing chrome yellow pigments of comparable shade.

Process for improving the application properties of pigment yellow 13

When diazotizing lower alkyl esters of 3-nitro-4-aminobenzoic acid and coupling them onto 5-(2'-hydroxy-3'-naphthoylamino)-benzimidazolone-(2) which may be substituted in 6'-position by chlorine or bromine, in 1-position by methyl or ethyl and in the benzo-nucleus by chlorine, bromine, methyl, ethyl, methoxy or ethoxy, and such as further illustrated by a representative formula ##STR1## wherein R is alkyl of 1 to 4 carbon atoms, X is hydrogen, chlorine, bromine, methyl, ethyl, methoxy or ethoxy, Y is hydrogen, methyl or ethyl, and Z is hydrogen, chlorine or bromine. Colorants are obtained which are especially useful for pigmenting plastics, spinning masses, printing inks, varnishes and paints. The dyeings obtained therewith are fast to light, weathering, solvents and migration, especially fast to overvarnishing and bleeding.

Monoazo compounds derived from 3-nitro-4-amino-benzoates and

When diazotizing a p-amino-benzoic acid anilide, the anilide nucleus of which is substituted in its paraposition by carbamoyl, acetamino or chloro and coupling it onto 5-acetoacetylamino-benzimidazolone-(2) monoazo pigments are obtained having a high fastness to light, solvents, overlacquering and bleeding and a very high heat resistance.

Azo compounds deriving from amino benzoic acid anilides and

Process for the aftertreatment of the azo pigment of the formula ##STR1## C.I. PIGMENT ORANGE 36 wherein the crude pigment obtained after coupling is heated to temperatures from 100.degree. to 150.degree. C. in dry or wet condition in a solvent which is water-immiscible or not indefinitely water-miscible and the pigment is isolated in known manner. The pigment aftertreated in this way shows substantially improved hiding power while the same pigment prepared in the usual way has poor hiding power and can not be used in stoving lacquers.

Azo pigment having improved hiding power and a process for its

2,5-Bis-(4'-aminophenyl)-1,3,4-oxadiazoles which are chlorinated in the phenyl nuclei are obtained by condensing hydrazine or a hydrazine yielding agent with equal or different chlorinated benzoic acids or acylating acid derivatives having in para-position to the acid group an amino group or a group capable of being transformed into the amino group, and, thereafter, effecting ring closure of the so-obtained bis-hydrazide to yield the oxadiazole. The products are bis-diazo components, especially for pigments having a very high tinctorial strength, clear and pure shades, a good fastness to light, to heat and to solvents.

Growing community of inventors

Kelkheim, Germany

Klaus Hunger