Hoechst Aktiengesellschaft

Heinrich Frolich

Klaus Hunger

Hasso Hertel

Joachim Ribka

Kurt C Habig

Hans-Joachim Lenz

The invention relates to a novel crystallographic modification (.beta.-modification) of the pigment of the formula I ##STR1## The .beta.-modification shows reflections in the Cu-K.sub..alpha. radiation X-ray diffraction spectrum at the following diffraction angles 2.theta. (accuracy .+-.0.2.degree.): at 21.95.degree. a maximum of high intensity, at 5.40.degree., 7.30.degree., 10.85.degree., 14.50.degree. and 27.60.degree. maxima of medium intensity and at 10.05.degree., 12.80.degree., 16.40.degree., 17.95.degree., 24.65.degree. and 25.80.degree. maxima of low intensity. The .beta.-modification is obtainable by coupling diazotized N-(3-amino-4-methylbenzoyl)-sulfanilic acid in an aqueous medium in the presence or absence of an organic solvent onto alkali-dissolved 2-hydroxy-4'-methoxy-3-naphthanilide and laking the coupling product by adding a calcium salt, at least one cation-active surfactant having been added at the latest prior to laking, and heating an aqueous suspension of the laked azo dye at a temperature of 130.degree. to 180.degree. C. The .beta.-modification is suitable for pigmenting printing inks, surface coatings, plastic compositions, filaments and paper, in particular for pigmenting polystyrene, copolymers based on polystyrene, polyolefins, copolymers of polyolefins and polyvinyl chloride.

.beta.-modified crystalline fed monoazo pigment

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

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:

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

Mixtures of monoazo compounds which are obtainable by diazotizing 0.75 to 0.85 molar equivalent of 5-nitro-2-amino-anisol and 0.25 to 0.15 molar equivalent of 3-nitro-4-amino-anisol and coupling onto 2-acetoacetylamino-anisol are pigments of high tinctorial strength, transparency, gloss and fastness to light having good rheological properties.

Pigments of mixtures of methoxynitrobenzene-azo-methoxy-acetanilides

Water insoluble yellow monoazo dyestuffs of the general formula 1 ##STR1## in which R.sub.1 represents alkyl, cycloalkyl or aralkyl, X represents a carboxylic acid ester or a carboxylic acid amide, and Y.sub.1 and Y.sub.2 represent hydrogen, chlorine or bromine, alkyl or alkoxy, and method for their preparation. The dyestuffs are valuable pigments, which may be used for dyeing lacquers, lacquer forming agents, natural or synthetic resins and polymers and for printing textile fibrous materials or paper. They are distinguished by good rheological properties and they are fast to light, weather and migration. Moreover, they are resistant to heat and show color intensity and pure shades.

Growing community of inventors

Niedernhausen/Taunus, Germany

Heinrich Frolich