Basf Aktiengesellschaft

Reinhard Sappok

Joachim Kranz

Rudolf Polster

Alois Wiesenberger

Eduard Hartmann

Wolf D Fechner

Karl Roth

Werner Jettmar

Fritz Guellich

Robert Nett

A process for the preparation of pigmentary forms of phthalocyanine and of insoluble polycyclic compounds, wherein the crude pigment is milled in the presence of one or more acids which have a pK of &lt;4.9 and are non-oxidizing under the milling conditions, until the primary particle size is .ltoreq.0.1 .mu.m, the milled material is then finished in the conventional manner in a solvent in the presence or absence of water, and the pigment is isolated. The pigments give very deep colorations and are very easily dispersible in the media in which they are used.

Preparation of easily dispersible and deeply colored pigmentary forms

Phthalocyanine formulations which comprise a mixture of (a) phthalocyanine and (b) from 2 to 20% by weight, based on (a) of one or more urea derivatives of the formula K-(-NHCO-NH-R).sub.2 (I), where K is 1,5-naphthylene or 4,4'-diphenylenemethane, R is alkyl of 12 to 18 carbon atoms, alkenyl of 12 to 18 carbon atoms, 3-(alkoxy of 8 to 18 carbon atoms)-propyl, 2-(alkylamino of 8 to 18 carbon atoms)-ethyl or (CH.sub.2).sub.3 --O--(CH.sub.2 --CH.sub.2 O).sub.n --R.sup.1, R.sup.1 is alkyl of 2 to 8 carbon atoms or phenyl and n is 1, 2, 3 or 4, and which are obtained by milling (a) with (b) in the absence of a grinding medium. When used in printing inks, such as offset printing inks, the formulations give deeply colored prints in very pure hues, with very low graininess of the ink.

Phthalocyanine formulations

Formulations of flavanthrone, pyranthrone, indanthrone, indigo, quinacridone, perylene-3,4,9,10-tetracarboxylic acid dianhydride and perylene-3,4,9,10-tetracarboxylic acid diimide pigments which contain, as additives, one or more compounds of the formula ##STR1## where X is an n-valent radical of a flavanthrone, pyranthrone, indigo, quinacridone, perylene-3,4,9,10-tetracarboxylic acid dianhydride or perylene-3,4,9,10-tetracarboxylic acid diimide pigment, R.sup.1, R.sup.3 and R.sup.4 are hydrogen or chlorine, R.sup.2 is hydrogen, chlorine, carboxyl, bromine, nitro, N-C.sub.1 -C.sub.5 -alkylcarbamyl, N-phenylcarbamyl or benzoylamino and n is 1, 2, 3 or 4. In solutions of surface-coating binders or of surface coatings, the above formulations give very deep colorations, coupled with high gloss and high transparency of the resulting films.

Pigment formulations

A pigment formulation which comprises (a) a finely divided organic pigment and (b) one or more urea derivatives of the formula K--(NH--CO--NH--R).sub.2, where R is C.sub.12 -C.sub.18 -alkyl, C.sub.12 -C.sub.18 -alkenyl, C.sub.8 -C.sub.18 -alkoxypropyl or --(CH.sub.2).sub.3 --O--(C.sub.2 H.sub.4 O).sub.n --R.sup.1, R.sup.1 is C.sub.2 -C.sub.8 -alkyl or phenyl, n is 1, 2, 3 or 4 and K is 1,5-naphthylene or 4,4'-diphenylenemethane, with or without (c) up to 5% by weight, based on (a and b), of agents conventionally present in pigment formulations. In binder solutions, the pigment formulations give printing inks and paints possessing excellent tinctorial properties. Some of the compounds (b) prevent the conversion of .alpha.-copper phthalocyanine to the .beta.-modification.

A phthalocyanine formulation which is stabilized against recrystallization and change of modification and which contains, as the stabilizer (a) a finely divided phthalocyanine as the pigment and (b) a salt or the corresponding homogeneous mixture of (.alpha.) a phthalocyanine derivative, which carries basic groups ##STR1## (R.sup.1 = H, alkyl of 1 to 20 carbon atoms, unsubstituted or substituted phenyl, --C.sub.2 H.sub.4 --NH).sub.z H or --(C.sub.3 H.sub.6 --NH).sub.z H, z = 1, 2 or 3, and R.sup.2 = H, alkyl of 1 to 6 carbon atoms or cycloalkyl of 6 to 8 carbon atoms) and (.beta.) an aliphatic sulfonic acid of 8 to 20 carbon atoms, a monoalkylbenzenesulfonic acid or dialkylbenzenesulfonic acid where alkyl is of 6 to 20 carbon atoms, or a monoalkylnaphthalenesulfonic acid or dialkylnaphthalenesulfonic acid where alkyl is of 6 to 20 carbon atoms, which acids may be substituted by hydroxyl, the molar ratio of .alpha.:.beta. being from 1:1 to 1:5, and, if desired, one or more organic fluids or solutions of resins in these fluids. The formulations are stable even in aromatic hydrocarbons and produce pure, deep colorations which have high gloss.

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Heidelberg, Germany

Reinhard Sappok