Hoechst Aktiengesellschaft

Reinhold Deubel

Heinz Uhrig

Joachim Weide

Klaus Ehl

Manfred Schneider

Helmut Diery

Erwin Dietz

Rudiger Jung

Franz Schui

Karl-Hermann List

Volker Hemmerling

Hans-Tobias Macholdt

Martin Hille

Konrad Opitz

Hubert Kruse

Alexander Sieber

Wolfgang Teige

Max Grossmann

Siegfried Schwerin

Wolfgang Wagemann

Norbert Wester

Manfred Zimmermann

Rainer Schunck

Erich Ackermann

Wolfgang Klinner

Werner Reitz

Erich Dietz

Werner Pasche

Rolf Staal

Werner Marx

Christa Uhde Nee Schilling

Water-insoluble azo colorants, their preparation and use The invention relates to monoazo and disazo compounds of the formula (I) ##STR1## in which D is the radical of a carbocyclic or heterocyclic diazo or bisdiazo component, R.sup.1 and R.sup.2, independently of one another, are each a substituted or unsubstituted aryl or heteroaryl radical, X.sup.1 and X.sup.2, independently of one another, are each ring-forming ether oxygen or a substituted or unsubstituted imide grouping and n has the value 0 or 1, in which rings A and B, independently of one another, can each be additionally substituted and/or carry substituted or unsubstituted fused rings. These new compounds of the formula (I) are obtained by coupling diazotized amines or diamines of the type D--NH.sub.2 or H.sub.2 N--D--NH.sub.2 with (benzoxazol-2-yl)- or (benzimidazol-2-yl)-arylacetamides. Depending on the presence and length of alkyl chains, the compounds of the formula (I) are suitable for use as pigments, disperse dyes or oil-soluble dyes.

Monoazo or disazo pigments based on (benoxazol-2-yl)- or

The invention relates to surface-active compounds of the general formula (I) ##STR1## in which Ar is an aromatic system which is optionally substituted by C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.18 -alkoxy, C.sub.2 -C.sub.5 -alkanoyl, C.sub.6 -C.sub.10 -aryl, (C.sub.6 -C.sub.10 -aryl)-C.sub.1 -C.sub.4 -alkyl, A has the formula --(X--O).sub.n --Y, wherein n denotes 1 to 50, X denotes ethylene or methylethylene and all or some of Y denote an acyl radical of a non-modified or modified natural resin acid and the other radicals Y denote radicals from the group comprising hydrogen, acyl radicals of saturated C.sub.1-24 -carboxylic acids, unsaturated C.sub.3-24 -carboxylic acids, C.sub.2-24 -hydroxy-fatty acids or C.sub.8-18 -alkyl-, -alkenyl- and -alkylidene-succinic acids, maleic acid, fumaric acid, sulfosuccinic acid, sulfuric acid, benzodicarboxylic acids and C.sub.1-16 -n-alkanedicarboxylic acids, W is a group --CHR-- or --CHR--N(R*)--T--N(R*)--CHR--, wherein R*is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -hydroxyalkyl, a radical A or --C.sub.2 -C.sub.4 -alkylene-O--A and R is H or C.sub.1-9 -alkyl, T is C.sub.2 -C.sub.12 -alkylene, which is optionally interrupted by --O-- or --NR'--, R' is H, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -hydroxyalkyl, A or C.sub.2 -C.sub.4 -alkylene-O--A, W* is H or --CHR--N(R*)--T--N(R*)A and m is 1 to 16. The compounds are prepared on the basis of oxyalkylated novolaks of the formula (I) in which all the radicals Y denote hydrogen. The polyalkylene glycol chains are now terminally esterified or half-esterified in a one- or multi-stage reaction in accordance with the definition of A. The resulting surface-active products are suitable as emulsifiers and dispersing agents for the most diverse fields of applications.

Resin acid esters based on novolak oxyalkylates, their preparation and

The invention relates to compounds of the formula (I) ##STR1## where D.sup.1 and D.sup.2 are each independently of each other unsubstituted or substituted aryl or hetaryl. The compounds are obtained by diazotizing one or more amines of the formula D-NH.sub.2 where D has the meaning D.sup.1 or D.sup.2 as per the formula (I) and coupling with 0.5 mole of 1,5-diazabicyclo[3.3.0]octane-2,4,6,8-tetrone per mole of total reacting diazonium salts. Depending on the presence and length of alkyl chains the compounds are suitable for use as pigments, disperse dyes or even fat dyes.

Water-insoluble disazo colorants having hetero-bicyclic methylene-active

Surface-active compounds on the basis of arylated fatty substances and

Process for specifically influencing the triboelectric effect of azo pigments in electrophotographic toners or developers or in powders for surface coating by adding to the azo pigments at the coupling reaction stage, at the laking stage or in the course of finishing at least one saltlike, cationic compound whose positively charged center is a nitrogen, phosphorus, arsenic or antimony atom or the group ##STR1## and use of such azo pigments for producing toners or developers used for the electrophotographic copying or manifolding of originals or for printing electronically, optically or magnetically stored data or in colorproofing or use of such azo pigments for producing powders or powder coatings used for the surface coating of articles made of metal, wood, plastics, glass, ceramics, concrete, textile material, paper or rubber.

Specifically influencing the triboelectric effect of azo pigments

Nitrogen-containing condensation products based on unmodified or modified natural resins, process for the preparation thereof and the use thereof. The invention relates to surface-active agents of the general formula

Nitrogen-containing condensation products based on unmodified or

According to the invention, addition of one or more surfactants having a cloud point in aqueous solution to an aqueous suspension of a solid gives after the isolation of the solid at a temperature above the cloud point aqueous press cakes containing a large amount of this solid. The direct processing of press cakes as obtained for example after the synthesis and isolation of dyes or pigments to give practical aqueous pastes or dispersions requires a minimum solids content in the press cakes. The minimum content is frequently not obtained when conventional methods of isolation are used, so that it is necessary to proceed via the indirect route of drying to obtain the powders and redispersing the powders. By using the process according to the invention it is possible to cut out the costly indirect route or, if desired, to reduce the expense of drying to obtain powders by an appreciable margin.

Process for preparing highly concentrated aqueous press cakes of solids

According to the invention, addition of one or more surfactants having a cloud point in aqueous solution to an aqueous suspension of an azo disperse dye gives after the isolation of the dye at a temperature above the cloud point aqueous press cakes containing a large amount of this dye. The direct processing of press cakes as obtained for example after the synthesis and isolation of azo disperse dyes to practical dispersions for use requires a minimum dye content in the press cakes. The minimum content is frequently not obtained when conventional methods of isolation are used, so that it is necessary to proceed via the indirect route of drying to obtain powders and redispersing the powders. By using the process according to the invention it is possible to cut out the costly indirect route or, if desired, to reduce the expense of drying to obtain powders by an appreciable margin.

Process for preparing a highly concentrated aqueous press cakes of an

Easily dispersible dust-free pigment granules of high tinctorial strength are obtained by adding to the aqueous suspension of a finely divided pigment, an alkaline solution of from 25 to 90 weight percent based on the weight of the granules obtained, of colophony or a colophony derivative, acidifying the mixture, subjecting it to a flush process while stirring and heating to a temperature, above the softening point of the resin, up to 100.degree. C. and isolatng the granules obtained. The granules are particularly suitable for preparing printing inks which are distinguished by a very high tinctorial strength, a good transparency and a low viscosity.

Process for preparing pigment granules from aqueous suspension of

A novel crystallographic modification (.beta.-modification) of the pigment C. I. Pigment Red 53:1 is described and claimed which has characteristic reflection values in its X-ray diffraction pattern obtained by means of Cu-K.sub..alpha. radiation. This novel pigment form is obtained by reacting an aqueous solution of an alkali metal or ammonium salt of the formula 1 ##STR1## with the equivalent amount of a water-soluble barium salt in the presence of a compound of the formula 2 ##STR2## The modification is distinguished by a more yellowish-red shade as compared to the known .alpha.-modification.

.beta.-modified crystalline red pigment

The invention relates to readily dispersible strong pigment formulations containing arylpararosanilinesulfonic acid pigments of the formula ##STR1## and a polyester resin which has been water-solubilized by neutralizing the carboxyl groups with nitrogen bases. The pigment formulations are distinguished by being very readily dispersible in the various printing ink binders and by having a high tinctorial strength.

Pigment formulation, a process for its preparation, and its use

By coupling diazotized amines of the benzene series onto acetoacetic acid arylides, in which process more than one diazo and/or coupling component is applied and from 0.1 to 20 molar % of the diazo and/or coupling component contain acid groups, and by subsequently reacting the reactive acid groups of the product obtained by coupling with cation-active quaternary compounds, recrystallization-resistant monoazo pigment mixtures are obtained which are suitable for the preparation of varnishes, printing inks, and oily and aqueous compositions.

Recrystallization-resistant monoazo pigment mixtures of high tinctorial

Aryl-pararosaniline sulfonic acid pigments can be transformed into a pigment preparation having high tinctorial strength and being easily dispersible by dissolving them in aqueous alkali, adding a water-soluble synthetic resin (being a reaction product or mixture of (I) maleic anhydride addition product of an unsaturated fatty acid or fatty acid polyol ester, said addition product being partially esterified with a polyol, and (II) a low-molecular curable and partially etherified aminoplast and optionally an anionic or nonionic surfactant and precipitating the preparation with a mineral acid. These preparations are especially useful for pigmenting printing inks, carbon paper, duplicating papers and typewriter ribbons.

Pigment preparations; process for their manufacture and their use

Compounds of the formula ##STR1## in which Y denotes an aryloxy group, which is possibly substituted, R.sub.4 and R.sub.5 denote hydrogen or C.sub.1 -C.sub.4 -alkyl, m denotes 0 to 12 and Z denotes polyalkylene glycol radicals having about 8 to about 200 ethylene glycol units --(CH.sub.2 --CH.sub.2 O)-- or up to about 200 ethylene glycol units and alkylene glycol units of the formula ##STR2## in which R.sub.6 is methyl or ethyl and in which at least 8 ethylene glycol units are present. These compounds are prepared by initially reacting epoxide with a phenol or naphthol and subsequently oxalkylating. The reaction products are used as dispersants for the preparation of aqueous pigment dispersions.

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Bad Soden am Taunus, Germany

Reinhold Deubel