Hoechst Aktiengesellschaft

Frank Prokschy

Erwin Dietz

Ernst Spietschka

Manfred Urban

Adolf Kroh

Gustav Kapaun

Heinrich Hamal

Michael Kappert

Derivatives of 9-oxo-1,9a,10-triaza-9-hydroanthracene of the general formula I ##STR1## with the exception of three compounds in which R denotes a hydrogen atom, halogen atom, an alkyl-C.sub.1 -C.sub.4, alkoxy-C.sub.1 -C.sub.4 or denotes a trihalogenomethyl group, a --CO--NH.sub.2, --CO--NH--(alkyl-C.sub.1 -C.sub.4) or --CO--N(alkyl-C.sub.1 -C.sub.4).sub.2 group or phenyl, alkyl-C.sub.1 -C.sub.4, --NH.sub.2, --NH(alkyl-C.sub.1 -C.sub.4), --N(alkyl-C.sub.1 -C.sub.4).sub.2 or an alkylene-C.sub.1 -C.sub.4 --OSO.sub.3 H group, bound via the bridge member --S--, --SO--or --SO.sub.2 --, a or a fused-on 4- to 7-membered isocycle or heterocycle, which itself can be part of a polycyclic system, from the series consisting of naphthalene, acenaphthene, phenanthrene and indole, x denotes an integer from 1 to 4, where for x&gt;1 R can be identical or different, and z denotes a fused-on 4- to 7-membered isocycle or heterocycle, which itself can be part of a polycyclic system, from the series consisting of naphthalene, acenaphthene, phenanthrene and indole, in which each of the 4- to 7-membered isocycles or heterocycles and each of the polycyclic systems mentioned can be substituted, processes for their preparation and their use for the coloring of natural or synthetic materials.

Substituted polycylic derivatives of the

Pigments of the formula I ##STR1## where A is a five- or six-membered aromatic fused or unfused heterocycle which contains one to three hetero atoms from the series consisting of nitrogen and/or oxygen and/or sulfur and which is bonded to the methylene group via a carbon atom, R.sub.1 and R.sub.2 are each hydrogen, alkyl C.sub.1 -C.sub.4, alkylene C.sub.2 or aryl, and together R.sub.1 and R.sub.2 may also be an aliphatic or aromatic ring, R.sub.3 is hydrogen, alkyl C.sub.1 -C.sub.4 hydroxylkyl C.sub.1 -C.sub.3 or alkylene C.sub.2, P is the radical of a polycyclic pigment or a radical of a mix-crystal of polycyclic pigments, and n is a number from 0.0001 to 0.2, are useful for pigmenting high molecular weight materials in the form of plastic materials, melts, spinning solutions, surface coatings, paints, printing inks, baking finishes of the class of the alkyd melamine resin or acrylic melamine resin finishes, two-component coatings based on polyisocyanate-crosslinkable acrylic resins and printing inks based on nitrocellulose.

Pigments and use thereof

A process for the preparation of 2-(arylamino)-3-carboxy-9(10H)-acridones of the formula A ##STR1## in which R and R' represent hydrogen, fluorine, chlorine or bromine atoms, alkyl(C.sub.1 -C.sub.4)-, oxalkyl(C.sub.1 -C.sub.4)- or carbonamide groups and x and y denote integers from 1 to 4, by cyclizing 2,5-diarylaminoterephthalic acids of the formula D ##STR2## in which R, R', x and y have the meanings mentioned previously, in a 5- to 15-fold amount by weight of polyphosphoric acid (P.sub.4 O.sub.10 content 80 to about 85%) or of an acidic polyphosphate (P.sub.4 O.sub.10 contents 75 to about 85%) as a water-abstracting agent at about 60.degree. C. to about 100.degree. C.

Process for the preparation of 2-(arylamino)-3-carboxy-9(10H)-acridones

Pigments of the quinacridonequinone series consisting of 98-20 mol percent of a quinacridonequinone of the general formula (1) ##STR1## in which R denotes a hydrogen or chlorine atom or a methyl or carbonamide group and m and n are 1 or 2, and 1-65 mol percent of a quinacridone of the general formula (2) ##STR2## in which R, m and n have the abovementioned meaning, and 1-15 mol percent of one or two acridone derivatives of the general formulae (3) and/or (4) ##STR3## in which X denotes O or NH and R can be identical or different and, like m and n, has the abovementioned meaning, the added compounds of the general formulae (2), (3) and/or (4) being predominantly incorporated into the crystal lattice if the quinacridonequinone of the general formula (1), processes for their preparation and their use for coloring synthetic and naturally occurring materials.

Pigments of the quinacridonequinone series, processes for their

Process for the preparation of linear quinacridones of the formula (1) ##STR1## in which R denotes a hydrogen, fluorine, chlorine or bromine atom or a C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.3 -alkoxy or phenyl group or a fused benzene ring or a phenylamino or phenoxy group which can be substituted on the aromatic nucleus by fluorine, chlorine or bromine atoms or C.sub.1 -C.sub.4 -alkyl groups, and n denotes a number from 0 to 2, it being possible, in the event that n.noteq.0, for the substituents R present on the same benzene ring or on the two benzene rings to be identical or different, by the oxidation of linear 6,13-dihydroquinacridones of the formula (2) ##STR2## in which R and n have the meanings mentioned above, which comprises heating, at temperatures from about 180.degree. C. to about 280.degree. C., 1 mole of the last-mentioned compounds with 1 to 2 moles of iodine in a high-boiling organic solvent which is inert towards the reactants.

Process for the preparation of linear quinacridones

Pigments of the quinacridonequinone series comprising 99-30 mole percent of a quinacridonequinone of the formula (1) ##STR1## in which R denotes a hydrogen or chlorine atom or a methyl group, 0-60 mole percent of a quinacridone of the formula (2) ##STR2## in which R has the above-mentioned meaning, and 1-10 mole percent of a 7,15-dihydro-pyrido-(2,1-b)-(1',2'; 1,2)-pyrimido-(4,5-g)-quinazoline-7,15-dione of the formula (3) ##STR3## in which R has the above-mentioned meaning, the added compounds of the formulae (2) and (3) being present in the crystal lattice of the quinacridonequinone of the formula (1), process for their preparation and their use for coloring plastic materials and for preparing automotive paints for metallic coatings.

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Frankfurt am Main, Germany

Frank Prokschy