MXPA99010918A - Use of mixed crystals of pigments on the basis of quinacridones in electrophotographic toners or developers, powder lacquers and ink-jet-inks - Google Patents

Abstract

Mixed crystal quinacridone pigments are used as colorants in electrophotographic toners and developers, powders, powder lacquers, ink-jet inks, hot-melt ink-jet inks, electret fibers and color filters The use of mixed crystal quinacridone pigments as colorants in electrophotographic toners and developers, powder lacquers, ink-jet inks, electret fibers and color filters is claimed. The pigments consist of 85-99 wt.%unsubstituted quinacridone (IA) of the b-phase and 1-15 wt.%substituted quinacridone(s) (IB). The use of mixed crystal quinacridone pigments as colorants in electrophotographic toners and developers, powder lacquers, ink-jet inks, electret fibers and color filters is claimed. The pigments consist of 85-99 wt.%unsubstituted quinacridone (IA) of the b-phase of formula (I):R1, R2=hydrogen (H) and 1-15 wt.%substituted quinacridone(s) (IB) of formula (I);R1, R2 independently=chlorine, bromine or fluorine or 1-4 carbon (C) alkyl, 1-4 C alkoxy or carbonamido groups, optionally substituted by 1-6 C alkyl groups;R1 may also=H Independent claims are also included for products, comprising electrophotographic toners and developers, powders and powder lacquers, ink-jet inks and hot-melt ink-jet inks, containing the pigment.

Description

USE OF MIXED GLASS PIGMENTS OF THE SERIES OF QUINACRIDONE IN TONERES AND REVELATORS ELECTROFOTOGRAFICOS, VARNISHES IN POWDER AND INKS FOR PRINTING BY INK JETS The present invention relates to the use of new types of mixed crystal pigments in toners and electrophotographic developers, powder coatings and inks for ink jet printing (Ink-Jet). In electrophotographic recording processes, a "picture of latent charges" is generated on a photoconductive element. This "image of latent charges" is revealed by the application of an electrostatically charged toner (also known as a toner), which is then transferred, for example, to paper, textile goods, films or synthetic materials, and is fixed, for example, by the action of pressure , radiation, heat or solvents. Typical toners are powder toners of one or two components (also known as one- or two-component developers), and special toners are also used, such as, for example, magnetic or liquid toners, latex toners and toners. polymerization. A measure for the quality of a toner is its specific charge q / m (charge per unit mass). Together with the sign and the magnitude of the electrostatic charge, a decisive quality criterion is, above all, the rapid achievement of the magnitude of the desired load and the constancy of this charge during a prolonged period of activation time. In addition, toner insensitivity to climatic influences, such as temperature and humidity, is another important criterion for additional suitability. Toners that can be charged both positively and negatively are used in photocopiers, laser printers, LED printers (Light Emitting Diodes), LCS (Liquid Crystal Shutter = liquid crystal shutters) or other digital printers on an electrophotographic basis, depending on the type of the procedure and the device. i o In order to obtain electro-photographic toners or developers with charge or positive or negative, agents for the control of the loads are added frequently. As a color-generating component (chromogen), typically colored organic pigments are used in the toners. The colored pigments have, because of their insolubility in the medium of In this case, there are considerable advantages over dyes, such as, for example, better thermostability and fastness to light. Based on the principle of "subtractive color mixing", with the help of the three primary colors, yellow, cyan and magenta, you can reproduce the entire spectrum of colors that are visible to the human eye. 2 o Only when the respective primary color meets exactly defined color requirements, an exact reproduction of the color is possible. In another case, some color tones may not be reproduced, and the color contrast is not sufficient.

In the case of toners of all colors, the three yellow, cyan and magenta toners must be exactly matched to each other, as well as to the precisely defined chromatic requirements, also in terms of their triboelectric properties, since they are transmitted consecutively in the same device. It is known that coloring agents are able to influence persistently on the triboelectric charge of toners. Because of the various triboelectric effects of the coloring agents and the influence, in part very pronounced, on the ability of the toners to be charged, it is not possible to simply add the coloring agents to a basic recipe for a toner, once it has been processed. Rather, it may be necessary to elaborate a recipe for each coloring agent, for which the type and quantity of the agent for the control of the loads must be specially established., what is needed. This procedure is correspondingly expensive and then, in the case of color toners for a process ink, still contributes additionally to the difficulties that have already been described above. Furthermore, it is important for the practice that the coloring agents possess a high thermostability and a good dispersibility. The typical temperatures of incorporation of the dyes in the toner resins are between 100 C and 200 C in the case of using kneaders or extruders. Correspondingly, a thermostability of 200 C, better than 250 C is a great advantage. It is also important that the thermostability is guaranteed for a prolonged period of time (approximately 30 minutes) and in different systems of binding agents. Typical binding agents for toners are polymerization, polyaddition and polycondensation resins, such as styrene, styrene and acrylate resins, styrene and butadiene, acrylate, polyester, phenol and epoxide resins, polysulfones or polyurethanes, individually or in combination. Fundamentally, there is a need for colored pigments, which have as high a transparency as possible, a good dispersibility and a small electrostatic effect, if possible neutral triboelectric. By a "neutral triboelectric proper effect" it is understood that the pigment does not manifest as far as possible any impact on the electrostatic charge of the resin itself and easily follows a defined adjustment of the charges, eg by means of an agent for the control of the charges. Transparency is of paramount importance, since when copying or printing in all colors, the yellow, cyan and magenta colors are copied or printed respectively on one another, with the order of succession of colors depending on the apparatus. If, then, a color above is not sufficiently transparent, the color below it may not be sufficiently translucent and color reproduction distorts. When copying or printing on sheets from above (overhead), transparency is even more important, since in this case a defective transparency even of only one color makes all the projection of the images appear gray. The present invention was based on the mission of providing color pigments for use in toners and electrophotographic developers, powder coatings, inks for ink jet printing, color filters and fibers with electret, which meet the above requirements. The problem posed by this mission was solved surprisingly by the use of the quinacridone mixed crystals defined below. The object of the present invention is the use of mixed crystal pigments of the quinacridone series, consisting of a) 85 to 99% by weight, especially 87 to 95% by weight, of unsubstituted quinacridone in the phase, which has the general formula (I), wherein R and R 'signify hydrogen atoms, and from b) 1 to 15% by weight, especially 5 to 13% by weight, of one or more substituted quinacridones having the general formula (I), wherein the substituents R 1 and R 2 are the same or different and represent chlorine, bromine or fluorine atoms, or C 1 -C 4 alkyl, C 1 -C 4 alkoxy or carboxamido groups, which may be substituted with C C β alkyl groups, and R 1 may additionally be hydrogen, quality of coloring agents in toners and electrophotographic developers, powder coatings, inks for ink jet printing, fibers with electret and color filters. Mixtures of quinacridones consisting of 85 to 99% by weight of quinacridone unsubstituted in the phase, and 1 to 15% by weight of one or more, especially 1 or 2, quinacridones substituted in various ways, form crystals under certain conditions mixed, which are also called solid solutions. By "mixed crystals" is meant that one or more component (s) added to a crystalline phase, most often in a non-stoichiometric ratio, and the host compound, crystallize in a common lattice. The X-ray diffraction pattern of a mixed crystal presents only the reflections of the crystalline lattice - sometimes enlarged - of the host compound or of a similar or clearly distinct crystal lattice, while in the X-ray diffraction diagram of the corresponding Mechanical mixing the reflections of all the components appear. In the mixed crystal pigments used according to the invention, substituted (b) quinacridones of the formula (I) are preferred, wherein R 1 signifies hydrogen, chlorine atoms or methyl or carboxamido groups, and R 2 means chlorine atoms or methyl groups or carboxamido. The color properties of the mixed crystal pigments according to the invention differ considerably from those with the corresponding mechanical blends of the individual components. These have, in particular, shades of purer colors and have higher coloring forces. In addition, color tones can be obtained that can not be adjusted with the individual components or with the mixed crystals known from the prior art, especially in the region of reddish violet. The fastnesses are excellent. The mixed crystal pigments described above can be prepared by cyclizing the 2,5-dianiino-terephthalic acid which forms the basis of compound a) and the substituted terephthalic acid (s) which constitutes ) the base of the compound (b), in a ratio of from 85: 15 to 99: 1, especially from 87: 13 to 95: 5, in the presence of a polyphosphoric acid and / or esters of polyphosphoric acids, hydrolyzing under pressure the mixture from the ring closure, which occurs after the cyclization, with water or diluted phosphoric acid, at a temperature of at least 110 C, preferably from 110 to 180 C, particularly preferably from 135 to 165 C , and then isolating the mixed crystal pigment, optionally after a fine division step and / or after a finishing treatment. A quantity of 3 to 10 times higher, preferably 3 to 5 times higher, amount of a polyphosphoric acid or its methyl ester, based on dianilino-terephthalic acid, is generally used as the ring closure agent. The P2O5 content of the polyphosphoric acid or its ester is preferably between 80 and 85% by weight, preferably between 83 and 85% by weight, corresponding to a phosphoric acid equivalent of 110 to 120%. Larger quantities of the ring closure agent can be used, but this is not necessary in general. The ring closure temperature is generally 80 to 150 C, preferably 120 to 140 C. In the ring closure reaction, inert solvents such as, for example, aromatic hydrocarbons may also be present. The time that passes until the total cyclization is usually 0, 5 to 24 hours, but most of the time only from 1 to 2 hours. The ring closure mixtures which occur after cyclization are hydrolysed under pressure at a temperature of at least 110 C with water or dilute phosphoric acid, optionally in the presence of an inert organic solvent under the reaction conditions, e.g. eg aromatic hydrocarbons. For hydrolysis, water or dilute phosphoric acid is used. In such case, the ring closure mixture is metered in under pressure into the water or diluted phosphoric acid. However, you can also proceed in the reverse way. The hydrolysis can be carried out in a continuous or batchwise regime. Advantageously, it is carried out continuously in a static mixer. Generally, referred to the polyphosphoric acid, a greater amount in 2 to 10 times of water or diluted phosphoric acid will be used. The duration of the hydrolysis is dependent on the rate of metered addition of the ring closure melt, for example 0.5 to 24 hours, preferably 0.5 to 5 hours. Through the choice of dianilino-terephthalic acids, the conditions of ring closure and hydrolysis at high temperatures, pigments of mixed crystals suitable for use are obtained immediately after hydrolysis, which can be isolated according to methods usual It may be advantageous to subject the finely divided mixed crystals, which have thus been obtained (in the present idiomatic idiom, hereinafter referred to as "prepigments"), to a finishing treatment at elevated temperatures, or first of all to produce coarse pigments of mixed crystals with coarse crystallinity, which are advantageously subjected to a fine mechanical division, and which directly or after a finishing treatment are transformed into a pigment form suitable for use. The mixed crystal pigments, optionally after intermediate isolation, are subjected to a subsequent treatment with or without addition of solvents at a temperature of 50 to 2001 C and, after having separated the liquid medium, they are isolated. The liquid medium can preferably have an alkaline pH value, for example a pH of 7.5 to 13. The coarse pigments of mixed crystals with coarse crystallinity are subjected to a fine fine mechanical division and then the mixed crystal pigments obtained in in this case they are isolated in the usual way or the mixed crystal pigments which have been obtained in this case, possibly after an intermediate insulation, are subjected to a finishing treatment, as previously described, and after having separated the liquid medium, are isolated. The fine division can be carried out by dry or wet milling. Preferably, a wet grinding with high energy input is carried out, since the crude pigment of mixed crystals does not have to be dried for this purpose. For dry milling, all discontinuous and continuous oscillating or rolling mills are suitable, and for wet milling all ball mills with stirring, rolling and discontinuous and continuous oscillating, as well as kneading machines are suitable. In order to improve the color properties and to achieve certain coloristic effects, solvents, pigment dispersants, surfactants, defoamers, extenders and other additives can be added at any point of the process. Mixtures of these additive materials can also be used. Surfactants which are to be used in the process are, for example, cationic, anionic or nonionic surfactants, preferably taurides of fatty acids, fatty acid sarcosides, (fatty alcohol) -polyglycol ethers, esters of (fatty alcohol) - polyglycols, alkyl polyglycol ether sulfates, (alkyl phenol) polyglycol ethers, alkane sulphonic acids and their salts, (alkyl phenyl) sulphonic acids and their salts, and (alkylphenol) -polyglycol ether sulfates. As pigment dispersants, which can be applied in the process, compounds having the general formula (II) are used wherein P represents a radical with the valence m of a linear quinacridone of the general formula (I), in which R1 and R2 are the same and represent hydrogen atoms or methyl groups, X represents a group of the formula (III) -COOM (III) or a group of the formula (IV) -SO3M (IV) in which M denotes the hydrogen ion H + or the equivalent Mr r of a cation of a metal with the valence r, where r is the case corresponding then coincidentally one of the numbers 1, 2 or 3, as defined for example L1 +, Na1 +, K1 +, Mg2 +, C2 +, Sr2 *, Ba2 +, Mn2 +, Cu2 +, Ni2 +, Co2 +, Zn2 +, Fe2 +, Al3 +, Cr3 + or Fe3 +; or an ammonium ion or an alkyl ammonium ion, or X means a phthalimido-methylene group or a sulfonamido group. For each unit of weight of crude pigment, prepigment or pigment of mixed crystals, a total of between 0.1 and 20% by weight, preferably between 3 and 10% by weight of surfactants and / or pigment dispersants can be suitably added in total. Preferred organic solvents, which can be used in one or more stages of the preparation process, are alkanols, especially ethanol, propanoles, butanols and pentanols; amides of carboxylic acids of an aliphatic nature, in particular formamide or dimethylformamide; cyclic carboxylic acid amides, in particular N-methyl-pyrrolidone; aromatic hydrocarbons, such as, for example, toluene, xylenes or ethylbenzene; chlorinated aromatic hydrocarbons, such as, for example, chlorobenzene and o-dichlorobenzene. It was surprising and unpredictable that pure glass pigments of mixed crystals were obtained by high temperature hydrolysis, whereas according to US Pat. No. 3,160,510 pigments of quinacridone mixed crystals (and not mixtures) are obtained only when the unsubstituted quinacridone is contained in a clearly lower proportion than in the case of the present invention. In addition, according to the data of US Pat. No. 4,099,980, in the case of the solvolysis of ring closure mixtures with the aforementioned composition, mixed crystal pigments result in the phase of the unsubstituted quinacridone, while that in accordance with the present process result in pigments of mixed crystals, which occur in the phase. The mixed crystal pigments obtainable in accordance with the present invention are distinguished by outstanding color and rheological properties, especially by a high flocculation stability, easy dispersibility, good gloss performance and high coloring strength. In comparison with the mixed crystals hitherto known, such as, for example, European Patent Documents EP-A2-247,576 and EP 0 822 560 or EP 0 827 037, the use of the present mixed crystals of quinacridone leads to properties clearly improved colors in the toner. The toner, with the same concentration of the pigment used, shows a higher coloring force, a higher transparency and a more pure color tone. The electrostatic influence of the binder system is small and thus makes it possible to easily fine-tune the desired triboelectric load, for example by means of charge control agents. In addition, the preparation of the coloring agent in an environmentally friendly way leads to a more favorable overall ecological balance of the toner in colors. In addition to being used in toners and electrophotographic developers, the present mixed crystals can also be used as coloring agents in powders and varnishes, especially in triboelectrically or electrokinetically projected powder coatings, as they are applied to the surface coating of base objects, example, metals, wood, textiles, paper or rubber. The powder varnish or powder receives its electrostatic charge usually in accordance with one of the following two procedures: a) In the corona discharge process, the powder or powder varnish is conducted in front of a device charged for corona discharge and at the same time charged, b) in the triboelectric or electrokinetic process, the principle is used of the electricity generated by friction. As resins for powder coatings, epoxy resins, polyester resins containing carboxyl and hydroxyl groups, polyurethane and acrylic resins are typically employed, together with the usual hardening agents. Resin combinations also find use. Thus, for example, epoxy resins are frequently used in combination with polyester resins containing carboxyl and hydroxyl groups. In addition, the improved triboelectric influence of the coloring agent can lead to the improvement of the properties of the electret in dyed (pigmented) electret materials, based on the typical electret materials in polyolefins, halogenated polyolefins, polyacrylates, poly (acrylonitriles), polystyrenes or fluorinated polymers, such as for example polyethylene, polypropylene, poly (tetrafluoroethylene) and those of perfluorinated ethylene and propylene, or in polyesters, polycarbonates, polyamides, polyimides, poly (ether ketones), in poly (arylene sulfides), especially poly (phenylene sulphides), in polyacetals, cellulose esters, poly (alkylene terealates) as well as mixtures of these polymers. Electret materials have numerous sectors of use and can acquire their load by means of a corona or triboelectric loading operation (bibliography: GM Sessler, "Electrets", Topics in Applied Physics, volume 33, Springer Publishing, New York, Heidelberg , 20th edition, 1987). In addition, the enhanced triboelectric influence of the coloring agent can lead to improved separation performance of stained (pigmented) polymers, which are separated according to electrostatic separation procedures (Y. Higashiyau, J. of Electrostatics, 30, pages 203-212. , 1993). Correspondingly, the triboelectric proper effect of the pigments is also important for mass dyeing of synthetic materials. Likewise, the triboelectric proper effect is important in process and elaboration stages in which intense contact with friction is reached, such as, for example, spinning processes, sheet stretching processes or other forming processes. The present mixed crystals can be coloristically colored by mixing with other pigments. The mission is often to colorize the color tone in toners in electrophotographic colors, triboelectrically projected powder coatings or inks for ink jet printing and adapt it to the specific requirements for the application. For this purpose, other organic color pigments, inorganic pigments and dyes are especially recommended. Preferably, for coloring the color tone, other organic color pigments are used in mixtures with the mixed crystals of quinacridone in concentrations of between 0.01 and 50% by weight, preferably between 0.1 and 25% by weight, and particularly preferably between 0.1 and 15% by weight, based on mixed crystals. In this case, the pigments in additional organic colors can be taken from the group of azo pigments or polycyclic pigments. In an especially preferred variant, a bluish magenta quinacridone mixed crystal can be colored by types of yellowish or carmine pigments, such as for example P.R. 146, P.R. 207, P.R. 209, P.R. 186 or P.R. 48 in the sense of a mixture of 2 components. Mixtures of multiple components are also suitable. Greater steps of color tones are possible for example when using orange-colored pigments such as P.O. 62, P.O. 36, P.O. 34, P.O. 13, P.O. 43 o P.O. 5, or yellow pigments such as P.Y. 12, 13, 17, 83, 155, 180, 185 or 97. The mixtures can be prepared in the form of powders, by mixing press cakes, spray-dried press cakes, master batches, as well as by dispersion (extrusion , kneading, processes in roller mills, bead mills, Ultraturrax) in the presence of a support material or vehicle in solid or liquid form (inks on aqueous and non-aqueous basis) as well as by waterlogging (flushing) in the presence of a material of support or vehicle. If the coloring agent is used with high proportions (>; 5%) of water or a solvent, the mixing can then also proceed in the presence of elevated temperatures and in a manner supported by a vacuum. Especially in order to increase the brightness as well as in part simultaneously for the hue of the color tone, mixtures with organic dyes are recommended. As such, preference can be given to: water-soluble dyes, such as, for example, direct dyes, reagents and acids (Direct, Reactive and Acid Dyes), as well as solvent-soluble dyes, such as, for example, dyes in solution, dyes in dispersion and vat dyes (Solvent Dyes, Disperse Dyes and Vat Dyes). As individual examples, mention will be made of: C.l. Reactive Yellow 37, Acid Yellow 23, Reactive Red 23, 180, Acid Red 52, Reactive Blue 19, 21, Acid Blue 9, Direct Blue 199, Solvent Yellow 14, 16, 25, 56, 64, 79, 81, 82, 83: 1, 93, 98, 133, 162, 174, Solvent Red, 8, 19, 24, 49, 89, 90, 91, 109, 118, 119, 122, 127, 135, 160, 195, 212, 215, Solvent Blue 44, 45, Solvent Orange 60, 63, Disperse Yellow 64 and Vat Red 41. Dyes and pigments with fluorescent properties can also be used, such as 7LuminoIe (Riedel- De Haen), in concentrations of 0.0001 to 30% by weight, preferably from 0.001 to 15% by weight, very particularly preferably comprised between 0.001 and 5%, based on the mixed crystals, for example in order to prepare safe toners against counterfeits. Inorganic pigments, such as for example TiO2 or BaSO4, serve to lighten the color in mixtures. In addition, certain mixtures of quinacridone mixed crystals with pigments are suitable for generating effects, such as, for example, pigments to produce pearlescent luster, pigments of Fe2O3 (7 Paliochrome) as well as pigments based on cholesteric polymers which, depending on the angle of observation, provide different impressions color. The mixed crystals used according to the invention can also be combined with numerous agents for the control of the loads, which control those of positive or negative sign, in order to achieve good capacities for loading in application techniques. It is also possible a simultaneous use of agents for the control of positive and negative charges. Possible agents for the control of fillers are, for example: triphenylmethanes; ammonium and imonium compounds; mineral compounds; fluorinated ammonium compounds and fluorinated imonium; amides of bis-cationic acids; polymeric ammonium compounds; diallylammonium compounds, aryl sulfide derivatives; phenol derivatives; phosphonium compounds and fluorinated phosphonium compounds; calix (n) arenes; bound oligosaccharides in the form of rings (cyclodextrins) and their derivatives, especially their derivatives of esters containing boron, inter-polyelectrolyte complexes (IPECs); salts of polyesters; complex compounds with metals, especially complexes of salicylates with metals and salicylates with non-metals; complexes of -hydroxycarboxylic acids with metals and non-metals; benzimidazolones; azines, thiazines or oxazines, which are exposed in the Color Index as pigments, dyes in solution (Solvent Dyes), basic dyes (Basic Dyes) or acid dyes (Acid Dyes). Examples of agents for the control of fillers, which can be combined individually or in combination with the mixed crystal pigment according to the invention, are: triarylmethane derivatives such as, for example: Pigment Blue 1, 2: 2 , 3, 8, 9, 9: 1, 10, 10: 1, 11, 12, 14, 18, 19, 24, 53, 56, 57, 58, 59, 61, 62, 67 of the Color Index, or example the Solvent Blue 2, 3, 4, 5, 6, 23, 43, 54, 66, 71, 72, 81, 124, 125 of the Color Index, as well as the triarylmethane compounds listed in the Color Index with the names of Acid Blue and Basic Dye, provided they are appropriate in terms of thermal stability and processability, such as, for example, Basic Blue 1, 2, 5, 7, 8, 11, 15, 18, 20, 23, 26, 36, 55, 56, 77, 81, 83, 88, 89 of the Color Index, the Basic Green 1, 3, 4, 9, 10 of the Color Index, adapting in turn the Solvent Blue 125, 66 and 124 of the Color Index. Solvent Blue 124 of the Color Index is particularly well suited in the form of its very crystalline sulphate or of trichloro-triphenylmethyl tetrachloro-aluminate. Metal complexes with CAS numbers 84179-66-8 (azo complex with chromium), 115706-73-5 (azo complex with iron), 31714-55-3 (azo complex with chromium), 84030-55-7 (salicylate complex with chromium), 42405-40-3 ( salicylate complex with chromium) as well as the quaternary ammonium compound CAS-n1 116810-46-9, as well as the complex azo dyes with aluminum, carboxylates and sulphonates of metals. Examples of agents for the control of fillers, of the series of the triphenylmethanes, well suited for the production of fibers with electret, are the compounds described in German patent documents DE-A-1,919,724 and DE-A -1,644,619. Of particular interest are certain triphenylmethanes, as described in U.S. Pat. No. 5,051,585, especially those of the formula (2) wherein R1 and R3 are phenylamino groups, R2 is a m-methyl-phenylamino group and the radicals R4 to R10 are all hydrogen. Further suitable are certain ammonium and imonium compounds, as described in US-A-5,015,676, as well as certain fluorinated ammonium and imonium compounds, as described in US-A-5,069,994, especially US Pat. of the formula (3) 2. 3 R13-CF: CH-CH2-N '33 (") (3) R 43 wherein R13 means perfluorinated alkyl with 5 to 11 carbon atoms, R23, R33 and R43 are the same or different, and mean alkyl with 1 to 5, preferably 1 to 2, C atoms, and Y is a stoichiometric equivalent of an anion , preferably of a tetrafluoro-borate or tetraphenyl-borate anion.

Further suitable are bis-cationic acid amides, as described in WO 91/0172, especially those of the formula (4) wherein R14, R24 and R34 are the same or different alkyl radicals with 1 to 5 C atoms, preferably methyl, n represents an integer from 2 to 5, and Z represents a stoichiometric equivalent of an anion, preferably an anion of tetraphenyl borate. Certain diallyl ammonium compounds are suitable, as described in DE-A-4,142,541, especially those of the formula (5) wherein R15 and R25 mean alkyl groups or different with 1 to 5, preferably 1 or 2, C atoms, but especially represent methyl groups and A represents a stoichiometric equivalent of an anion, preferably a tetraphenyl borate anion, as well as the polymeric ammonium compounds of the formula (6) obtainable therefrom, as described in DE-A-4,029,652 and DE-A-4,103,610, wherein n has a value corresponding to molecular weights of 5,000 to 500,000 g / mol, preferably at molecular weights of 40,000 to 400,000 g / mol. Further suitable are certain aryl sulphide derivatives, as described in DE-A-4,031,705, especially those of the formula (7) wherein R17, R27, R37 and R47 mean the same or different alkyl groups with 1 to 5, preferably 2 or 3, C atoms, and R, 57 is one of the bivalent radicals -S-, -SS-, -SO - or SO2- For example, R17 to R47 are propyl groups and R57 is the -SS- group. Certain phenol derivatives are also suitable, as described in EP-A-0,258,651, especially those of the formula (8) wherein R18 and R38 mean alkyl or alkenyl groups with 1 to 5, preferably 1 to 3, C atoms, and R28 and R48 mean hydrogen or alkyl with 1 to 3 C atoms, preferably methyl. Also suitable are certain phosphonium compounds and fluorinated phosphonium compounds, as described in US-A-5,021,473 and US-A-5,147,748. Certain calix (n) arenes are additionally suitable, as described in EP-A-0,385,580, EP-A-0,516,434 and Angew. Chemie (1993), 195, 1258. Certain compounds which are complex with metals, such as azo complexes with chromium, cobalt, iron, zinc or aluminum or complexes of salicylic acid or boric acid with chromium, cobalt, iron, zinc or aluminum, are also suitable. of the formula (14) wherein M means a bivalent metal central atom, preferably a chromium, aluminum, iron, boron or zinc atom, R114 and R214 mean linear or branched alkyl groups, same or different, with 1 to 8, preferably 3 to 6, atoms of C, such as for example tere-butyl. Further, certain benzimidazolones are also suitable, as described in EP-A-0,347,695. Further, certain linked oligosaccharides in the form of rings are suitable, as described in DE-A-4,418,842, especially those of the formula (16) wherein n 6 is a number between 3 and 100, R 116 and R .216 have the meaning of OH, OR, J316D, meaning R 316 alkyl (CrC18), aryl (C6-C12) or substituted toluene-sulfonyl or unsubstituted, and X16 has the meaning of CH2OH or CH2COR316. As examples, there will be mentioned: n16 = g ^ R11ß and R216 = QH; ? 16 _ C | _ | 2? H n16 _ 7j R116 and R216 _ QHJ? 16 _ ^ QH n16 = 8, R 16 and R216 = OH, X16 = CH2OH. Further suitable are certain polymer salts, as described in DE-A-4,332,170, whose anionic component is a polyester, consisting of the product of the reaction of the individual components a), b) and c) as well as optionally d) and optionally e), being a) a dicarboxylic acid or a reactive derivative of a dicarboxylic acid, which are free of sulfo groups, b) an aromatic, aliphatic or cycloaliphatic difunctional sulfo compound, whose functional groups are hydroxyl or carboxyl, or hydroxyl and carboxyl, c) a diol, a polyether diol or an aliphatic, cycloaliphatic or aromatic polycarbonate diol, d) a polyfunctional compound (functionality> 2), whose functional groups are hydroxyl or carboxyl, or hydroxyl and carboxyl, and e) a monocarboxylic acid, and whose cationic components are hydrogen atoms or metal cations. Further suitable are certain cyclo-oligosaccharide compounds, as described for example in DE-A-19711260, which are obtainable by reacting a cyclodextrin or a cyclodextrin derivative with a compound of the formula .OR1 HO • B \. OR2 wherein R1 and R2 mean alkyl, preferably C1-C4 alkyl. Further suitable are certain inter-polyelectrolyte complexes, as described for example in DE-A 19732995. Particularly suitable in this case are the compounds, which have a molar ratio of polymeric cationic groups to polymeric anionic groups of 0.9. : 1, 1 to 1, 1: 0.9. They are additionally suitable, especially in the case of the application of mixed crystals of quinacridone in liquid toners (Handbook of Imaging Materials, 1991, Marcel Dekker, Inc. Kap.6 Liquid Toner Technology), certain ionic surfactants and the so-called metal soaps. . Particularly suitable are certain alkylated aryl sulphonates, such as barium petronatos, calcium petronatos, dinonil-naphthalene-barium sulfonates (basic and neutral), calcium dinonyl sulfonate or the sodium salt (Na) of dodecyl-benzene acid -sulfonic and polyisobutylene-succinimides (Chevrons Oloa 1200). Soy lecithin and polymers of N-vinyl pyrrolidone are further adapted. Sodium salts of phosphatized mono- and diglycerides with saturated and unsaturated substituents, AB-diblock copolymers based on A: polymers of 2- (N; N) -di-methylaminoethyl methacrylate quatemized with p-toluene-sulfonate are also suitable. methyl and B: poly (2-ethylhexyl methacrylate). Further suitable, in particular in liquid toners, are certain di- and tri-valent carboxylates, especially aluminum tristearate, barium stearate, chromium stearate, magnesium octoate, calcium stearate, iron naphthalate and zinc naphthalate. Furthermore, certain chelating agents are suitable for the control of chelating agents, as described in EP-0 636 945 A1, metal (ionic) compounds, as described in EP 0 778 501 A1, metal salts of phosphates, as described in the Japanese patent document JA 9 (1997) -106107, azines with the following numbers of the Color-lndex: Cl Solvent Black 5, 5: 1, 5: 2, 7, 31 and 50; C.l. Pigment Black 1, C.l. Basic Red 2 and C.l. Basic Black 1 and 2. The combination of a quinacridone mixed crystal and an agent for the control of the loads can be carried out by physical mixing, during the preparation of mixed crystals, during the finishing process or by corresponding application on the surface of the pigments of mixed crystals (coating with pigments). Both components can also be advantageously polymerized in the case of polymerization toners, in which the binder is polymerized in the presence of the pigment of quinacridone mixed crystals and the agent for the control of the charges, or they can be used in the preparation of liquid toners in inert solvents with high boiling points, such as hydrocarbons. The subject of the invention is therefore also an electrophotographic toner or developer, containing a binder for the toner, from 0.1 to 60% by weight, preferably from 0.5 to 20% by weight, of a crystal pigment mixed optionally nuanced and from 0 to 20% by weight, preferably from 0.1 to 5% by weight, in each case referred to the total weight of the toner or developer, of an agent for the control of the loads taken between the class of triphenylmethanes, ammonium and imonium compounds; fluorinated ammonium and imonium compounds; amides of bis-cationic acids; polymeric ammonium compounds; diallyl ammonium compounds; aryl sulfide derivatives; phenol derivatives; fluorinated phosphonium compounds and fluorinated phosphonium compounds; calix (n) arenes, cyclodextrins; salts of polyesters; complex compounds with metals; boron complexes of cyclo-oligosaccharides; inter-polyelectrolyte complexes; benzimidazolones; azines, thiazines or oxazines. Other components may also be added to the toner, such as waxes, which may be of animal, vegetable or mineral origin, artificial waxes or mixtures thereof. Waxes are substances that at 20 C are kneadable, hard from firm to brittle, crystalline from roughly to finely, from transparent to opaque, but are not vitreous. In addition, a protective agent against light can be added to the mixed crystal pigment in the toner. Subsequently, Free Flow Agents such as TiO2 or highly disperse silicic acid can be added to the toner.

Especially preferred are electrophotographic toners or developers, which as agents for the control of charges contain almost colorless compounds. Also the agents for the control of the charges can be added to the pigment in the form of a wet press cake, master batch or powder. Mixtures with the compounds of the above-mentioned formula (3) are preferred; of the aforementioned formula (5), in which R15 and R25 are in each case methyl and A? it is a tetraphenyl borate anion; of the formula (6) mentioned above, in which R15 and R25 are in each case methyl, A? is an anion of tetraphenyl borate and n has a value corresponding to molecular weights of 5,000 to 500,000; of the aforementioned formula (7); of the aforementioned formula (14); or with one of the above-mentioned polymer salts, whose anionic component is a polyester. The subject of the invention is furthermore a powder or a powder varnish, containing a polyester or acrylic resin with an epoxide, carboxyl or hydroxyl content, or a combination thereof, of 0.1 to 60% by weight, preferably 0.5 to 20% by weight of a mixed crystal pigment optionally shaded and from 0 to 20% by weight, preferably from 0.1 to 5% by weight, in each case based on the total weight of powder or powder coating or of an agent for controlling the charges of the classes and the preferred compounds mentioned above for electrophotographic toners. The pigment of quinacridone mixed crystals, which is used according to the invention, is advantageously incorporated in a concentration of 60% by weight, preferably 0.5 to 20% by weight, particularly preferably 0.1 to 5.0 % by weight, based on the total mixture, in the binder of the respective toner (liquid or dry), developer, powder varnish, electret material or the polymer to be separated by electrostatic means, for example by extrusion or incorporation by kneading, or is added to the polymerization process of the binder. In this case, the pigment of mixed crystals as well as the agents for the control of the aforementioned fillers are added in the form of dry and ground powders, dispersions or suspensions, for example in organic and / or inorganic solvents, of a press cake (which can be used eg for the so-called waterlogging process), spray-dried press cakes, as described below, batches, preparations, pastes pastes, as a compound applied on appropriate supports, such as eg ground of infusoria (Kieselgur), T0O2 or AI2O3, from an aqueous or non-aqueous solution or can be added in another form. The content of the mixed crystal pigment in the press cake and in the master batch is usually between 5 and 70% by weight, preferably between 20 and 50% by weight. In addition, the mixed crystal pigment can also be used as a highly concentrated press cake, especially as a spray dried press cake, the pigment content being in this case between 25 and 95% by weight, preferably between 50 and 95% by weight. 90% by weight. The preparation of the spray dried press cake can be carried out according to customary methods.

The magnitude of the electrostatic charge of the electrophotographic toners or powder varnishes, in which the pigment according to the invention is homogenously incorporated, can not be predicted and is measured with the aid of conventional test systems under the same conditions (same dispersion times, equal particle size distribution, same particle shape) at approximately 20 C and a relative humidity of 50%. The operation of electrostatically charging the toner is performed by swirling with a vehicle (carrier), with a standardized share in the crushing (3 parts by weight of toner by 97 parts by weight of vehicle, on a rolling bench (150 revolutions per minute Then the electrostatic charge (JH Dessauer, HE Clark, "Xerography and related Processes", Focal Press, NY, 1965, page 289) is measured at a conventional measuring station.; J.F. Hughes, "Electrostatic Powder Coating", Research Studies Press Ltd. Letchworth, Hertfordshire, England, 1984, chapter 2). The triboelectric projection of the (varnishes in) powders is carried out with a projector with a standardized projection tube and a star internal bar, at a maximum flow rate of the powder with a projection pressure of 3 bar. The object that has been subjected to projection is hung for it inside a projection cabin and is subjected to projection from a distance of approximately 20 cm directly from the front, without additional movement of the projector apparatus. The respective charge of the sprayed powder is then measured with a "measuring device for the measurement of the triboelectric charge of powders" of the entity Intec (Dortmund). For measurement, the measuring antenna of the measuring device is held directly inside the dust cloud that comes out of the projector. The intensity of current that is established from the electrostatic charge of a powder varnish or a powder is indicated in microamps (A). The rate of deposition or separation is then determined in% by differential weighing from the sprayed and deposited powder varnish. The transparency of the pigment of quinacridone mixed crystals in toner binding agent systems is investigated as follows: In 70 parts by weight of a crude binder (consisting of 15 parts by weight of the respective resin for toner and 85 parts by weight) weight of ethyl acetate) are incorporated by stirring with a dissolving apparatus 30 parts by weight of the pigmented test toner (for 5 min at 5,000 rpm). The binder agent for test toner thus produced is applied with a doctor blade to a conventional pigment binder produced in the same way, with a manual coater on an appropriate paper (eg, letterpress printing paper). An appropriate size of the doctor blade is, for example, the K bar N3 (= thickness of the applied layer with a scraper 24 m). The paper, for the best determination of the transparency, has a black bar printed, the transparency differences are determined in dL values according to DIN 55,988, or it is evaluated according to the test prescription Marketing Pigmente, Clariant GmbH "Visuelle und Farbmetrische Bewertung von Pigmenten "edition 3, 1996 (n1 1/1). In addition, quinacridone mixed crystal pigments were found to be suitable as coloring agents in inks for ink jet printing on an aqueous basis (including microemulsion inks) and on a non-aqueous (solvent-based) base as well as in the inks that work according to the hot melt principle. The inks in microemulsion are based on organic solvents, water and eventually an additional hydrotrope (interface mediator). The inks on a non-aqueous base contain essentially organic solvents and optionally a hydrotropic substance. Inks for hot melt processes are mostly based on waxes, fatty acids, alcohols or sulfonamides, which are in the solid state at room temperature and which are converted to the liquid state upon heating, the preferred margin being located of fusion between about 60 C and about 140 C. Also subject to invention is an ink for hot melt jet printing, which consists essentially of 20 to 90% by weight of a wax and of 1 to 10% by weight of the pigment of quinacridone mixed crystals. In addition, contents of from 0 to 20% by weight of an additional polymer (as "dye solubilizer"), from 0 to 5% by weight of a dispersing agent, from 0 to 20% by weight of a modifying agent can be found. of the viscosity, from 0 to 20% by weight of a plasticizer, from 0 to 10% by weight of a tackifier, from 0 to 10% by weight of a transparency stabilizer (which, for example, prevents crystallization of the waxes) as well as from 0 to 2% by weight of an antioxidant. Typical additive materials and adjuvants are described, for example, in US Pat. No. 5,560,760. The subject of the present invention are also liquids for ink jet recording, which contain one or more of the quinacridone mixed crystal pigments. The finished recording liquids generally contain in total from 0.5 to 15% by weight, preferably from 1.5 to 8% by weight (calculated on a dry basis) of pigments of quinacridone mixed crystals. The microemulsion inks contain from 0.5 to 15% by weight, preferably from 1.5 to 8% by weight, of a pigment of quinacridone mixed crystals, from 5 to 99% by weight of water and from 0.5 to 94.5% by weight of an organic solvent and / or a hydrotrope compound. The "solvent-based" ink jet printing inks preferably contain from 0.5 to 15% by weight of a pigment of quinacridone mixed crystals, from 85 to 94.5% by weight of an organic solvent and / or hydrotrope compounds. The water used for the preparation of the liquids for recording is preferably used in the form of distilled or desalinated water. In the case of the solvents contained in the recording liquids, it may be an organic solvent or a mixture of solvents of this type. Suitable solvents are, for example, uni- or plurivalent alcohols, their ethers and esters, for example alkanols, especially with 1 to 4 carbon atoms, such as, for example, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, bi-or ter-valent alcohols, especially with 2 to 5 carbon atoms, eg ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6 -hexanediol, 1, 2,6-hexanetriol, glycerol, diethylene glycol, dipropylene glycol, triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol; (lower alkyl) -privalent alcohol esters, such as, for example, mono-methyl-, -ethyl- or butyl-ethylene glycol ethers, triethylene glycol mono-methyl- and -ethyl ethers; ketones and ketone alcohols such as, for example, acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, methyl pentyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol; amides, such as, for example, dimethyl formamide, dimethyl acetamide, N-methyl pyrrolidone, toluene and n-hexane. As hydrotrope compounds, optionally also serving as solvents, for example, formamide, urea, tetramethyl urea, caprolactam, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, butyl glycol, methyl cellosolve can be used. , glycerol, N-methyl-pyrrolidone, 1,3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzene sulfonate, sodium xylene sulphonate, sodium toluene sulfonate, sodium cumene sulfonate, sodium dodecyl sulfonate , sodium benzoate, sodium salicylate or sodium butyl monoglycol sulfate. In addition, the recording liquids according to the invention can also contain customary additive materials, for example preserving agents, surface-active substances, cationic, anionic or non-ionogenic (surfactants and wetting agents), as well as agents for viscosity regulation, polyvinyl alcohol, cellulose derivatives, or water-soluble natural or artificial resins such as smoke-forming agents (film formers) or binders in order to increase the adhesion and abrasion resistance. Amines, such as, for example, ethanol-amine, diethanol-amine, triethanolamine, N, N-dimethylethanolamine or diisopropylamine, serve mainly to increase the pH value of the liquid for recording. These are normally present in a proportion of 0 to 10% by weight, preferably 0.5 to 5% by weight in the liquid for recording. The ink jet printing inks according to the invention can be prepared by dispersing the pigments of quinacridone mixed crystals in the form of a powder, as an aqueous or non-aqueous preparation, as a suspension or as a press cake in the form of a dispersion. the medium for microemulsion or in the non-aqueous medium or in the wax for the production of an ink for printing by hot-melt ink jet. The press cake can also be a highly concentrated press cake, especially spray dried. In addition, quinacridone mixed crystal pigments are also suitable as coloring agents for color filters, for both subtractive and color additive generation (P. Gregory "Topics in Applied Chemistry: High Technology Application of Organic Dye "Plenum Press, New York, 1991, pages 15-25.) In the following Examples the parts mean parts by weight and the percent means so many percent by weight.

EXAMPLE OF SYNTHESIS 1 392 parts of a polyphosphoric acid containing 85.0% P2O5 are metered into a pressure vessel. Thereafter, 70.5 parts of 2,5-dianilino-terephthalic acid and 7.8 parts of 2,5-di (4-toluidino) -terephthalic acid are added with stirring at 80 to 90 C, and the mixture is heated to 125.degree. C for 1 hour, closing rings to form quinacridone. Thereafter, the reaction mixture is metered into a second pressure vessel and, while stirring, is hydrolysed under pressure with a mixture of 1762 parts of a 30% phosphoric acid. % at a temperature of 140 C. In this way, the temperature rises to 155 C. It is stirred at 155 C for 3.5 hours. After that, it is cooled to 60 C, the mixed crystal pigment is filtered with suction, washed with water at neutrality and dried at 80 C. 70.2 parts of a mixed crystal pigment are obtained. The mixed crystal pigment spectrum is presented. This spectrum differs from the spectrum of the quinacridone without substitution in the phase by an additional reflex at 13.73 (2T). The typical reflections of 2,9-dimethyl-quinacridone at 11.05 and 32.01 (2T) are not detectable.

EXAMPLE OF SYNTHESIS 2 9 parts of a mixed crystal pigment, prepared according to Synthesis Example 1, and 1 part of a pigment dispersant with the general formula (II) are mechanically mixed. In this formula (II), P means the radical of the linear, unsubstituted quinacridone, and X means a group of the formula -SO2-NH- (CH2) 3-N (C2H5) 2.

EXAMPLE OF SYNTHESIS 3 382 parts of a polyphosphoric acid containing 85.0% P2O5 are metered into a pressure vessel. Thereafter, 64.9 parts of 2,5-dianiino-terephthalic acid and 11.5 parts of 2,5-di- (4-toluidino) -terephthalic acid are added with stirring at 80 to 90 ° C. 125 C for 1 hour, closing rings to form quinacridone. Then, the reaction mixture is metered into a second pressure vessel and hydrolysed under pressure with stirring with a mixture of 1721 parts of 30% phosphoric acid at a temperature of 140 C. In this way, the temperature rises to 155 C. It is stirred for 0.5 hours at 155 C. After that it is cooled to 60 C, the mixed crystal pigment is filtered with suction, washed with water at neutrality and dried at 80 C. 68 are obtained, 6 parts of a mixed crystal pigment. The mixed crystal pigment spectrum is presented. Typical reflections of 2,9-dimethyl-quinacridone are not detectable.

EXAMPLE OF SYNTHESIS 4 The procedure is the same as in Synthesis Example 3, with 68.6 parts of the mixed crystal pigment being subjected to an isobutanol finish. The mixed crystal pigment is mixed with 411.6 parts of water and 411.6 parts of isobutanol (100%), stirred at 150 C for 5 hours and then the sobutanol is distilled off.

ELECTROSTATIC PROPERTIES EXAMPLE OF APPLICATION 1 Parts of the mixed crystal pigment from Synthesis Example 1 are homogenously incorporated in powder form or as a corresponding amount of a presscake, by means of a kneader over the course of 30 minutes, into 95 parts of a toner binder (polyester based on bisphenol-A, 7Almacryl T500). It is then ground in a universal laboratory mill and then classified into a centrifugal classifier.

The desired fraction of particles (from 4 to 25 m) is activated with a vehicle, which consists of ferrite particles coated with silicone with a size of 50 to 200 m (bulk density 2.75 g / cm3) (FBM 96 - 100 , entity Powder Techn.). The measurement is carried out in a usual measuring station of q / m.

By using a screen with a mesh width of 25 m, it is ensured that in the toner blow-by blows, no vehicle is dragged together. The measurements are made with a relative humidity of approximately 50%. Depending on the duration of the activation, the following values of q / m [in C / g] are measured: EXAMPLES OF APPLICATION 2 TO 8 (BOX) The preparation of the toner and the measurements were carried out analogously to Application Example 1. In all the Examples the proportion of pigment of mixed crystals, calculated as dry mass, is 5%. The content of pigment in the press cake (Application examples 2 and 3) and in the master batch (Application example 7) is in each case 30%. In Application Examples 4, 5 and 6 the proportion of the agent for the control of the charges in the toner is in each case 1% and the proportion of the binder for toner is only 94% there.

PICTURE Agent A for the control of the loads: 0 R23, R33, R43 = C2 alkyl R13 = perfluoroalkyl (C5-Cn) Agent B for charge control: Agent C for the control of the loads: Alkyl-Cr-salicylate (7Bontron E84, Orient Chemicals). Application examples show that the pigments of quinacridone mixed crystals used according to the invention have a very good compatibility with the agents for the control of the charges. This makes it possible to fine-tune the triboelectric load according to the technical requirements for the devices. Already small quantities (1%) of agents for the control of the loads provide a constant load in the long term.

Transparency: The toner transparency of Application Example 1 was measured (with a layer thickness of 24 m) and compared to the transparency of a toner of the same type, which nevertheless contained as a coloring agent a pigment of mixed crystals according to the document EP-A-0,247,576, Example 3. The test toner according to the invention had an increased transparency in 3 to 4 evaluation steps (= was clearly more transparent), a shift of the color tone towards blue and a force highest colorant.

EXAMPLE 1 Inks for ink jet printing on aqueous and non-aqueous bases Parts of a finely milled 50% pigment preparation with a mixed crystal pigment of Synthesis Example 1 based on a copolymer of polyvinyl chloride and polyvinyl acetate (eg 7Vinol) 15/45 of the Wacker entity or 7Vilith AS 42 of the entity Huís), achieving a homogeneous pigment dispersion by introduction by intense kneading in the copolymer, are incorporated by stirring in a mixture of 80 parts of methyl isobutyl ketone and 1,2-propylene glycol parts by a dissolving apparatus. An ink for ink jet printing with the following composition is obtained: parts of a mixed crystal pigment, 5 parts of a copolymer of polyvinyl chloride and polyvinyl acetate, 10 parts of 1,2-propylene glycol, 80 parts of methyl isobutyl ketone.

EXAMPLE 2 To 5 parts of a pigment preparation of Synthesis Example 2, which is in the form of an ultrafine aqueous preparation of the 40% pigment, is added with agitation (with a paddle stirrer or dissolver) first 75 parts of water deionized and then 6 parts of 7Mowilith D760 (acrylate dispersion), 2 parts of ethanol, 5 parts of 1,2-propylene glycol and 0.2 part of 7Mergal K7. An ink for ink jet printing with the following composition is obtained: parts of a pigment preparation according to the Synthesis Example 2 6 parts of Mowilith DM 760 (acrylate dispersion) 2 parts of ethanol 5 parts of 1,2-propylene glycol 0.2 parts of Mergal K7 81, 8 parts of deionized water.

EXAMPLE 3 To 5 parts of a mixed crystal pigment of Synthesis Example 3, which is in the form of an aqueous ultrafine preparation at 40% by weight of the pigment, 80 parts of deionized water are added initially with stirring and then 4 parts. of 7Luviskol K30 (poly (vinylpyrrolidone), BASF), 5 parts of 1,2-propylene glycol and 0.2 part of Mergal K7. An ink for ink jet printing having the following composition is obtained: parts of a mixed crystal pigment 4 parts of Luviskol K30 (poly (vinylpyrrolidone)) 5 parts of 1,2-propylene glycol 0.2 parts of Mergal K7 85.8 parts of deionized water.

Claims (10)

NOVELTY OF THE INVENTION CLAIMS

1. - Use of pigments of mixed crystals of the quinacridone series, consisting of a) 85 to 99% by weight of quinacridone unsubstituted in the phase, having the general formula (I), wherein R1 and R2 mean hydrogen atoms, and b) 1 to 15% by weight of one or more substituted quinacridones having the general formula (I), wherein the substituents R1 and R2 are the same or different and mean chlorine, bromine or fluorine atoms, or C1-C4 alkyl, C1-C4 alkoxy or carboxamido groups, which may be substituted with CrC6 alkyl groups, and R1 may additionally be hydrogen, as coloring agents in toners and electrophotographic developers, lacquers powder, inks for ink jet printing, fibers with electret and color filters.

2. Use according to claim 1, characterized in that the mixed crystal pigment consists of 87 to 95% by weight of component a) and 5 to 13% by weight of component b).

3. - Use according to claim 1 or 2, characterized in that in b) the radical R1 means hydrogen, chlorine, methyl or carboxamido and the radical R2 means chlorine, methyl or carboxamido.

4. Use according to at least one of claims 1 to 3, characterized in that the pigment of mixed crystals is colored with another organic pigment in color, an inorganic pigment or a dye.

5. Use according to at least one of claims 1 to 4, characterized in that the mixed crystal pigment is used in combination with a charge control agent taken from the group of triphenylmethanes, ammonium and imonium compounds; mineral compounds, fluorinated ammonium compounds and fluorinated imonium compounds; amides of bis-cationic acids; polymeric ammonium compounds; diallyl ammonium compounds; aryl sulfide derivatives, phenol derivatives; phosphonium compounds and fluorinated phosphonium compounds; calix (n) -arenos; linked oligosaccharides in the form of rings and their derivatives, especially derivatives of boron esters, inter-polyelectrolyte complexes, polyester salts, complex compounds with metals, especially salicylate complexes with metals and salicylate complexes with non-metals; complexes of hydroxy-carboxylic acids with metals and non-metals, benzimidazolones; azines, thiazines or oxazines.

6. Use according to at least one of claims 1 to 5 in liquid toners or powder toners. 7.- Electrophotographic toners or developers, which contain a 4 binder for toners, from 0.1 to 60% by weight, preferably from 0.5 to 20% by weight, of a mixed crystal pigment optionally colored according to one of claims 1 to 4, and from 0 to 20% by weight , preferably from 0.1 to 5% by weight, in each case based on the total weight of powder or powder varnish, of a charge control agent taken from the class of triphenylmethanes, ammonium and imonium compounds; fluorinated ammonium and imonium compounds; amides of bis-cationic acids; polymeric ammonium compounds; diallyl ammonium compounds; aryl sulfide derivatives; phenol derivatives; phosphonium compounds and fluorinated phosphonium compounds; calix (m) arenes; cyclodextrins; salts of polyesters; complex compounds with metals; boron complexes of cyclo-oligosaccharides; inter-polyelectrolyte complexes; benzimidazolones; azines, thiazines or oxazines. 8. powder or varnish powder, containing a polyester or acrylic resin with a content of epoxide, carboxyl or hydroxyl groups, or a combination of such resins, from 0.1 to 60% by weight, preferably 0.5 to 20% by weight of a mixed crystal pigment optionally shaded according to one of claims 1 to 4, and from 0 to 20% by weight, preferably from 0.1 to 5% by weight, in each case based on the total weight of the powder or powder varnish, an agent for the control of charges of the class of triphenylmethanes, ammonium compounds and monomers; fluorinated ammonium and imonium compounds; amides of bis-cationic acids; polymeric ammonium compounds; diallyl ammonium compounds; aryl sulfide derivatives; derivatives of phenols, phosphonium compounds and fluorinated phosphonium compounds; calix (n) arenes; cyclodextrins; salts of polyesters; complex compounds with metals; boron complexes of cyclo-oligosaccharides, inter-polyelectrolyte complexes; benzimidazolones; azines, thiazines or oxazines. 9. Ink for ink jet printing, which contains from 0.5 to 15% by weight of a mixed crystal pigment according to one of claims 1 to 4. 10.- Ink for jet printing of fusion ink in hot, which consists essentially of 20 to 90% by weight of a wax and 1 to 10% by weight of a mixed crystal pigment according to one of claims 1 to 4.