PIGMENT PREPARATIONS CONTAINING DERIVATIVES OF AZOBARBITURIC ACID AND OF MELAMINE

Description

[0001] The present invention relates to novel pigment preparations based on metallazo pigments and fatty acids, processes for their preparation and their use as yellow pigment for coloring plastics.

[0002] Metal complexes of azobarbituric acid with nickel salts and their use as yellow pigments have long been known and widely described in the literature (see, for example, W. Herbst, K. Hunger: Industrial Organic Pigments, 3rd edition 2004, pp. 390 / 397). It is also known that these products can be further processed, e.g., with melamine or melamine derivatives, to improve the application properties of the pigments, for example, in the coloring of plastics, coatings, and color filters for LCDs.

[0003] The literature also describes that, in addition to nickel salts, metal azo complexes can also contain one or more salts of different metals to adjust their coloristic properties. Application EP-A 1 591 489 discloses metal complexes of azo compounds containing metals from the series of alkali metals, alkaline earth metals, and lanthanides, as well as aluminum, scandium, titanium, vanadium, chromium, manganese, cobalt, copper, nickel, and zinc, and optionally iron. The resulting pigments exhibit a different color locus compared to pure nickel-azobarbituric acid complexes.

[0004] Furthermore, it is known from the literature that the surface of pigments can be treated with additives. This surface coating is intended to improve, for example, the dispersing properties of the pigments. However, increasing coating on the pigment surface is always associated with a loss of color strength.

[0005] Such a surface treatment of azo pigments is known, for example, from "W. Herbst, K. Hunger, Industrial Organic Pigments (Production, Properties, Applications), 3rd Completely Revised Edition (2004), Wiley-VCH-Verlag , p. 202".

[0006] Pigments based on metallazobarbituric acid and melamine, which contain copper and nickel ions and optionally other metal ions, are known from JP 2010 111708 A, EP-A 3 072 932, and EP-A 3 222 680. The pigments known from EP-A 3 072 932 and EP-A 3 222 680 are characterized by improved dispersing properties.

[0007] The metallazo pigments known from the state of the art still require improvement with regard to their application characteristics, particularly with regard to their heat stability.

[0008] It has been found that compositions of metal azo pigments based on azobarbituric acid, nickel and copper salts and melamine and / or melamine derivatives and certain fatty acids surprisingly exhibit improved heat stability.

[0009] From an application perspective, heat stability is an important property of pigments. Improving this property opens up potential applications for these products in areas where high processing temperatures are required, for example, in the coloring of plastics such as polypropylene, polyester, and polyamide.

[0010] The invention therefore relates to pigment preparations, characterized in that they contain at least i) a metallazo pigment A) containing the components a) at least two metallazo compounds of the formula (I) which differ at least in the metal ion Me, or their tautomeric forms, wherein R 1< and R 2< independently of one another represent OH, NH 2 or NHR 5<, R 3< and R 4< independently of one another represent =O or =NR 5<, R 5< represents hydrogen or alkyl, preferably C 1 -C 4 alkyl, and Me represents a metal ion Me 1< or Me 2<, where Me 1< represents Cu 2+< or Ni 2+< and Me 2< represents Zn 2+<, Al 3+< 2 / 3, Fe 2+<, Fe 3+< 2 / 3, Co 2+<, Co 3+< 2 / 3, La 3+< 2 / 3, Ce 3+< 2 / 3, Pr 3< + 2 / 3-, Nd 2+<, Nd 3+< 2 / 3, Sm 2+<, Sm 3+< 2 / 3, Eu 2+< , Eu 3+< 2 / 3 , Gd 3+< 2 / 3 , Tb 3+< 2 / 3 , Dy 3+< 2 / 3 , Ho 3+< 2 / 3 , Yb 2+< , Yb 3+< 2 / 3 , Er 3+< 2 / 3 , Tm 3+< 2 / 3 , Mg 2+< , Approx 2+< , Sr 2+< , Mn 2+< , Y 3+< 2 / 3 , Sc 3+< 2 / 3 , Ti 2+< , Ti 3+< 2 / 3 , Nb 3+< 2 / 3 , Mo 2+< , Mo 3+< 2 / 3 , V 2+< , V 3+< 2 / 3 , Zr 2+< , Zr 3+< 2 / 3 , Cd 2+< , Cr 3+< 2 / 3 , Pb 2+< or Ba 2+< -, with the proviso that the amount of metal ions Me 1< is 97 to 100 mol% in total and the amount of metal ions selected from the series Me 2< is 0 to 3 mol% in total,in each case based on one mole of all compounds of formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum of the compounds of formula (I) is 99.9 : 0.1 to 0.1 : 99.9, and b) at least one compound of formula (II), wherein R 6< represents hydrogen or alkyl, preferably C 1 -C 4 alkyl which is optionally mono- or polysubstituted by OH, and ii) at least one aliphatic monocarboxylic acid B) having 10 to 22 C atoms in an amount of 70 to 210 g based on 1 mol of all metallazo compounds (I) contained in the metallazo pigment A).

[0011] In the case where Me in formula (I) represents a 3-valent metal ion, the charge balance is achieved by an equivalent amount of anionic structural units of formula (Ia) wherein R 1< , R 2< , R 3< and R 4< have the meaning given for formula (I).

[0012] Preferably, the components a) contained in the metal azo pigments A) together with the components b) form adducts.

[0013] Adducts are generally understood to be compound molecules. The bonding between the molecules can occur, for example, through intermolecular interactions, Lewis acid-base interactions, or through coordination bonds.

[0014] In the context of the present invention, the term adduct is intended to generally encompass all types of insertion and addition compounds.

[0015] The terms "intercalation compound" or "addition compound" in the context of the present invention are understood to refer, for example, to compounds formed through intermolecular interactions such as van der Waals interactions or Lewis acid-base interactions. The way in which the intercalation proceeds depends both on the chemical properties of the component to be intercalated and on the chemical nature of the host lattice. Such compounds are often also referred to as intercalation compounds. In the chemical sense, this refers to the intercalation of molecules, ions (rarely also atoms) into chemical compounds.

[0016] Furthermore, this also includes inclusion compounds, so-called clathrates. These are compounds of two substances, one of which is a guest molecule embedded in a lattice or cage made of a host molecule.

[0017] The terms "intercalation compound" or "addition compound" within the meaning of the present invention also include intercalation solid solutions (also known as interstitial compounds). These are chemical, non-stoichiometric, crystalline compounds composed of at least two elements.

[0018] Furthermore, the terms "intercalation compound" or "addition compound" within the meaning of the present invention also include compounds formed by coordinate bonds or complex bonds. Such compounds include, for example, substitutional solid solutions or exchange solid solutions, in which at least two substances form a common crystal and the atoms of the second component sit on regular lattice sites of the first component.

[0019] Compounds capable of forming an adduct with the compounds of formula (I) as defined above can be both organic and inorganic compounds. These compounds are referred to below as adduct formers.

[0020] In principle, suitable adduct formers come from a wide variety of compound classes. For purely practical reasons, compounds that are liquid or solid under standard conditions (25°C, 1 bar) are preferred.

[0021] Of the liquid substances, those which have a boiling point of 100°C or above, preferably greater than or equal to 150°C at 1 bar, are generally preferred. Suitable adduct formers are generally acyclic and cyclic organic compounds, e.g. aliphatic and aromatic hydrocarbons, which may be substituted, e.g. by OH, COOH, NH 2 , substituted NH 2 , CONH 2 , substituted CONH 2 , SO 2 NH 2 , substituted SO 2 NH 2 , SO 3 H, halogen, NO 2 , CN, -SO 2 -alkyl, -SO 2 -aryl, -O-alkyl, -O-aryl, -O-acyl.

[0022] Carboxylic acid and sulfonic acid amides are a preferred group of adduct formers; particularly suitable are urea and substituted ureas such as phenylurea, dodecylurea and others, as well as their polycondensates with aldehydes, especially formaldehyde; heterocycles such as barbituric acid, benzimidazolone, benzimidazolone-5-sulfonic acid, 2,3-dihydroxyquinoxaline, 2,3-dihydroxyquinoxaline-6-sulfonic acid, carbazole, carbazole-3,6-disulfonic acid, 2-hydroxyquinoline, 2,4-dihydroxyquinoline, caprolactam, melamine, 6-phenyl-1,3,5-triazine-2,4-diamine, 6-methyl-1,3,5-triazine-2,4-diamine, cyanuric acid.

[0023] Also suitable in principle as adduct formers are polymers, preferably water-soluble polymers, e.g. ethylene-propylene oxide block polymers, preferably with an M n greater than or equal to 1,000, in particular from 1,000 to 10,000 g / mol, polyvinyl alcohol, poly-(meth)-acrylic acids, modified cellulose, such as carboxymethylcelluloses, hydroxyethyl and -propylcelluloses, methyl and ethylhydroxyethylcelluloses.

[0024] According to the invention, adduct formers used are those of formula (II). Melamine is particularly preferred.

[0025] In general, the metallazo pigments A) present in the pigment preparations according to the invention contain 0.05 to 4 mol, preferably 0.5 to 2.5 mol and very particularly preferably 1.0 to 2.0 mol of compounds of the formula (II) per mol of compounds (I).

[0026] The metallazo pigments A) contained in the pigment preparations according to the invention can be physical mixtures of the adducts of a) at least two metallazo compounds of formula (I) and b) at least one compound of formula (II). These are preferably physical mixtures of the adducts of the pure Ni azo compound with melamine and the pure Cu azo compound with melamine.

[0027] However, the metallazo pigments contained in the pigment preparations according to the invention are particularly preferably the chemical mixed compounds of the adducts of a) at least two metallazo compounds of formula (I) and b) at least one compound of formula (II). These chemical mixed compounds are adducts of such metallazo compounds in which the Ni and Cu atoms, as well as optionally other metal ions Me 2<, are incorporated into a common crystal lattice.

[0028] The metal azo pigments A) contained in the pigment preparations according to the invention are preferably those which contain adducts of the components a) at least two metallazo compounds of the formula (I) given above, wherein R 1< and R 2< are OH, R 3< and R 4< are =O, Me 1< is Cu 2+< or Ni 2+< and Me 2< is Zn 2+< , Al 3+< 2 / 3 , Fe 2+< , Fe 3+< 2 / 3 , Co 2+< , Co 3+< 2 / 3 , La 3+< 2 / 3 , Ce 3+< 2 / 3 , Pr 3+< + 2 / 3- , Nd 2+< , Nd 3+< 2 / 3 , Sm 2+< , Sm 3+< 2 / 3 , Eu 2+< , Eu 3+< 2 / 3 , Gd 3+< 2 / 3 , Tb 3+< 2 / 3 , Dy 3+< 2 / 3 , Ho 3+< 2 / 3 , Yb 2+< , Yb 3+< 2 / 3 , Er 3+< 2 / 3 , Tm 3+< 2 / 3 , Mg 2+< , Ca 2+< , Sr 2+< , Mn 2+< or Y 3+< 2 / 3 , with the proviso that the amount of metal ions Me 1< is 97 to 100 mol% in total and the amount of metal ions Me 2< is 0 to 3 mol% in total, in each case based on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum of the compounds of the formula (I) is 0.3 : 99.7 to 30 : 70, and b) at least one compound of the above-mentioned formula (II) wherein R 6< is hydrogen.

[0029] The metallazo pigments A) contained in the pigment preparations according to the invention are particularly preferably those which contain adducts of the components a) at least two metallazo compounds of the formula (I) given above, wherein R 1< and R 2< are OH, R 3< and R 4< are =O, Me 1< is Cu 2+< or Ni 2+< and Me 2< is Zn 2+< , Al 3+< 2 / 3 , Fe 2+< , Fe 3+< 2 / 3 , Co 2+< , Co 3+< 2 / 3 , La 3+< 2 / 3 , Ce 3+< 2 / 3 , Pr 3+< + 2 / 3- , Nd 2+< , Nd 3+< 2 / 3 , Sm 2+< , Sm 3+< 2 / 3 , Eu 2+< , Eu 3+< 2 / 3 , Gd 3+< 2 / 3 , Tb 3+< 2 / 3 , Dy 3+< 2 / 3, with the proviso that the amount of metal ions Me 1< is a total of 99 to 100 mol% and the amount of metal ions Me 2< is a total of 0 to 1 mol%, in each case based on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum of the compounds of the formula (I) is 0.5 : 99.5 to 10 : 90, and b) at least one compound of the above-mentioned formula (II) wherein R 6< is hydrogen.

[0030] The metallazo pigments A) contained in the pigment preparations according to the invention are very particularly preferably those which contain adducts of the components a) at least two metallazo compounds of the above-given formula (I), wherein R 1< and R 2< are OH, R 3< and R 4< are =O, Me 1< is Cu 2+< Ni 2+< and Me 2< is Zn 2+< , Al 3+< 2 / 3 , Fe 2+< , Fe 3+< 2 / 3 , Co 2+< , Co 3+< 2 / 3, with the proviso that the amount of metal ions Me 1< is 99 to 100 mol% in total and the amount of metal ions Me 2< is 0 to 1 mol% in total, in each case based on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum of the compounds of the formula (I) is 1:99 to 5:95, and b) at least one compound of the above-given formula (II) wherein R 6< is hydrogen stands.

[0031] The metallazo pigments A) contained in the pigment preparations according to the invention are particularly preferably those which contain adducts of the components a) at least two metallazo compounds of the formula (I) given above, in which R 1< and R 2< are OH, R 3< and R 4< are =O and Me is a metal ion Me 1<, with the proviso that the amount of metal ions Me 1< is a total of 100 mol% based on one mole of all compounds of the formula (I), and the molar ratio of Cu to Ni metal ions in the sum of the compounds of the formula (I) is 1:99 to 5:95, and b) at least one compound of the formula (II) given above in which R 6< is hydrogen.

[0032] The metallazo pigments A) contained in the pigment preparations according to the invention generally have a BET specific surface area (m 2 < / g) of 50 to 200 m 2 < / g, preferably of 80 to 160 m 2 < / g and very particularly preferably of 100 to 150 m 2 < / g, determined according to DIN 66131 (determination of the specific surface area of ​​solids by gas adsorption according to Brunauer, Emmett and Teller (BET)).

[0033] Substituents in the meaning of alkyl denote, for example, straight-chain or branched C 1 -C 6 -alkyl, preferably C 1 -C 4 -alkyl, which may optionally be mono- or polysubstituted by identical or different substituents, for example by halogen, such as chlorine, bromine or fluorine; -OH, -CN, -NH 2 or C 1 -C 6 -alkoxy.

[0034] The metallazo pigments A) contained in the pigment preparations according to the invention are known from EP-A 3 072 932 and EP-A 3 222 680 and can be prepared in a known manner as described therein.

[0035] For example, the metal azo pigments A) are obtainable by reacting the components a) at least two metallazo compounds of formula (I) which differ at least in the metal ion Me, or their tautomeric forms, wherein R 1< and R 2< independently of one another represent OH, NH 2 or NHR 5<, R 3< and R 4< independently of one another represent =O or =NR 5<, R 5< represents hydrogen or alkyl, preferably C 1 -C 4 alkyl, and Me represents a metal ion Me 1< or Me 2<, where Me 1< represents Cu 2+< or Ni 2+< and Me 2< represents Zn 2+<, Al 3+< 2 / 3, Fe 2+<, Fe 3+< 2 / 3, Co 2+<, Co 3+< 2 / 3, La 3+< 2 / 3, Ce 3+< 2 / 3, Pr 3< + 2 / 3-, Nd 2+<, Nd 3+< 2 / 3, Sm 2+<, Sm 3+< 2 / 3, Eu 2+< , Eu 3+< 2 / 3 , Gd 3+< 2 / 3 , Tb 3+< 2 / 3 , Dy 3+< 2 / 3 , Ho 3+< 2 / 3 , Yb 2+< , Yb 3+< 2 / 3 , Er 3+< 2 / 3 , Tm 3+< 2 / 3 , Mg 2+< , Approx 2+< , Sr 2+< , Mn 2+< , Y 3+< 2 / 3 , Sc 3+< 2 / 3 , Ti 2+< , Ti 3+< 2 / 3 , Nb 3+< 2 / 3 , Mo 2+< , Mo 3+< 2 / 3 , V 2+< , V 3+< 2 / 3 , Zr 2+< , Zr 3+< 2 / 3 , Cd 2+< , Cr 3+< 2 / 3 , Pb 2+< or Ba 2+< -, with the proviso that the amount of metal ions Me 1< is 97 to 100 mol% in total and the amount of metal ions selected from the series Me 2< is 0 to 3 mol% in total,each based on one mole of all compounds of formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum of the compounds of formula (I) is 99.9 : 0.1 to 0.1 : 99.9, with the components b) at least one compound of formula (II), wherein R 6< represents hydrogen or alkyl, preferably C 1 -C 4 alkyl which is optionally mono- or polysubstituted by OH.

[0036] The metallazo compounds (I) can be prepared, for example, by reacting alkali salts of the formula (III), wherein X represents an alkali metal ion, preferably a sodium or potassium ion, R 1< and R 2< independently represent OH, NH 2 or NHR 5<, R 3< and R 4< independently represent =O or =NR 5<, and R 5< represents hydrogen or alkyl, preferably C 1 -C 4 alkyl, or their tautomers, preferably the sodium or potassium salts, with nickel and copper salts and optionally one or more Me 2< metal salts from the series of Zn 2+< -, Al 3+< -, Fe 2+< -, Fe 3+< -, Co 2+< -, Co 3+< -, La 3+< -, Ce 3+< -, Pr 3+< -, Nd 2+< -, Nd 3+< -, Sm 2+< -, Sm 3+< -, Eu 2+< -, Eu 3+< -, Gd 3+< -, Tb 3+< -, Dy 3+< -, Ho 3+< -, Yb 2+< -, Yb 3+< -, Er 3+< -, Tm 3+< -, Mg 2+< -, Ca 2+< -, Sr 2+< -, Mn 2+< -, Y 3+< -, Sc 3+< -, Ti 2+< -, Ti 3+< -, Nb 3+< -, Mo 2+< -, Mo 3+< -, V 2+< -, V 3+< -, Zr 2+< -, Zr 3+< -, Cd 2+< -, Cr 3+< -, Pb 2+< - and Ba 2+< - salts, wherein 0.001 to 0.999 mol of at least one nickel salt, 0.001 to 0.999 mol of at least one copper salt and 0.03 to 0 mol of at least one metal salt from the series of the Me 2< metal salts mentioned are used per mole of compound of the formula (III).

[0037] Preferably, 0.7 to 0.997 mol of at least one nickel salt and 0.003 to 0.3 mol of at least one copper salt and 0.03 to 0 mol of at least one metal salt from the series of Me 2< metal salts are used per mole of compound of formula (III).

[0038] Particularly preferably, 0.9 to 0.995 mol of at least one nickel salt and 0.005 to 0.1 mol of at least one copper salt and 0.03 to 0 mol of at least one metal salt from the series of the Me 2< metal salts mentioned are used per mole of compound of formula (III).

[0039] Very particular preference is given to using 0.95 to 0.99 mol of at least one nickel salt and 0.01 to 0.05 mol of at least one copper salt and 0.03 to 0 mol of at least one metal salt from the series of the salts of the Me 2< metal salts mentioned per mole of compound of formula (III).

[0040] Particularly preferably, 0.95 to 0.99 mol of at least one nickel salt and 0.01 to 0.05 mol of at least one copper salt are used per mol of compound of formula (III).

[0041] In general, 0.05 to 4 mol, preferably 0.5 to 2.5 mol and very particularly preferably 1.0 to 2.0 mol of compound of formula (II) are used per mol of compound of formula (I).

[0042] The process for preparing the metallazo pigments A) is generally carried out at a temperature of 60 to 95 °C in aqueous solution at a pH below 7. The nickel and copper salts to be used, and any other Me 2< metal salts that may be used, can be used individually or as a mixture with one another, preferably in the form of an aqueous solution. The compounds of formula (II) can also be added individually or as a mixture with one another, preferably in the form of solids.

[0043] In general, the process for preparing the metal azo pigments A) is carried out in such a way that the azo compound of the formula (III), preferably as the Na or K salt, is initially charged, that one or more of the compound or compounds of the formula (II) to be incorporated or added, preferably melamine, is added and then, simultaneously or successively, is reacted with at least one nickel salt and at least one copper salt and optionally one or more Me 2< metal salts, preferably in the form of aqueous solutions of these salts, preferably at pH values ​​below 7. Suitable agents for adjusting the pH value are sodium hydroxide solution, potassium hydroxide solution, sodium carbonate, sodium bicarbonate, potassium carbonate and potassium bicarbonate.

[0044] Preferably, water-soluble nickel and copper salts are suitable, in particular chlorides, bromides, acetates, formates, nitrates, sulfates, etc. Preferably used nickel and copper salts have a water solubility of more than 20 g / l, in particular more than 50 g / l at 20°C.

[0045] As Me 2< metal salts, preferably their water-soluble salts are suitable, in particular their chlorides, bromides, acetates, nitrates and sulfates, preferably their chlorides.

[0046] The metallazo pigments A) obtained in this way can then be isolated as an aqueous filter cake by filtration of their aqueous suspension. This filter cake can be dried, for example, after washing with hot water, using conventional drying methods.

[0047] Possible drying processes include, for example, paddle drying or spray drying of corresponding aqueous slurries.

[0048] The pigment can then be ground again.

[0049] The metallazo pigments A) contained in the pigment preparations according to the invention can also be prepared by mixing the adducts of metallazo compounds of the formula (I) in which Me is Ni 2+< with adducts of metallazo compounds of the formula (I) in which Me is Cu 2+<, and optionally with one or more adducts of metallazo compounds of the formula (I) in which Me is a metal ion Me 2<.

[0050] The aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention may be saturated or mono- or polyunsaturated.

[0051] The aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention are preferably those which contain 10 to 22 C atoms and which are saturated or mono- to triunsaturated.

[0052] The aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention are particularly preferably those which contain 12 to 22 C atoms and which are saturated or mono- or diunsaturated.

[0053] Examples of such monocarboxylic acids B) to be used according to the invention are: n-Decanoic acid (capric acid, C 10 H 20 O 2 ), undec-10-enoic acid (undecylenic acid, C 11 H 20 O 2 ), dodecanoic acid (lauric acid, C 12 H 24 O 2 ), tetradecanoic acid (myristic acid, C 14 H 28 O 2 ), hexadecanoic acid (palmitic acid, C 16 H 32 O 2 ), octadecanoic acid (stearic acid, C 18 H 36 O 2 ) and (9Z)-octadec-9-enoic acid (oleic acid, C 18 H 34 O 2 ) and n-docosanoic acid (behenic acid, C 22 H 44 O 2 ).

[0054] The aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention are very particularly preferably those which contain 14 to 18 C atoms and which are saturated or monounsaturated.

[0055] In particular, the aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention are tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid) and (9Z)-octadec-9-enoic acid (oleic acid).

[0056] The aliphatic monocarboxylic acids B) can be obtained, for example, from Uniqema (ICI) either in pure form or as a carboxylic acid mixture.

[0057] The aliphatic monocarboxylic acids B) contained in the pigment preparations according to the invention can be present in pure form or as mixtures.

[0058] The mixtures of aliphatic monocarboxylic acid B) contained in the pigment preparations according to the invention are preferably mixtures comprising at least one saturated or monounsaturated aliphatic monocarboxylic acid having 14 C atoms, at least one saturated or monounsaturated aliphatic monocarboxylic acid having 16 C atoms and at least one saturated or monounsaturated aliphatic monocarboxylic acid having 18 C atoms.

[0059] The mixtures of aliphatic monocarboxylic acids B) to be used according to the invention preferably contain 0.5 to 5% by weight, preferably 1 to 3% by weight of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 14 C atoms, 25 to 60% by weight, preferably 30 to 50% by weight of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 16 C atoms and 40 to 75% by weight, preferably 45 to 65% by weight of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 18 C atoms.

[0060] The mixtures of aliphatic monocarboxylic acid B) contained in the pigment preparations according to the invention are particularly preferably mixtures containing myristic acid, palmitic acid and stearic acid in the preferred quantity ranges indicated above.

[0061] Such mixtures are known as commercial products from UNIQUEMA under the trade name "Pristerene®<", whereby the different chemical and quantitative compositions of these mixtures are characterized by a four-digit numerical code. Preferred according to the invention are Pristerene®< 4910, containing a mixture of 2 wt.% myristic acid, 30 wt.% palmitic acid, and 64 wt.% stearic acid; Pristerene®< 4911, containing a mixture of 2 wt.% myristic acid, 45 wt.% palmitic acid, and 52 wt.% stearic acid; Pristerene®< 4922, containing a mixture of 0.7 wt.% myristic acid, 30 wt.% palmitic acid, and 66 wt.% stearic acid; and Pristerene®< 9429.

[0062] The pigment preparations according to the invention generally contain 70 to 210 g of at least one aliphatic monocarboxylic acid B) based on 1 mol of all metallazo compounds (I) contained in the metallazo pigment A).

[0063] The pigment preparations according to the invention preferably contain 100 to 180 g, particularly preferably 120 to 160 g, of at least one aliphatic monocarboxylic acid B), in each case based on 1 mol of all metallazo compounds (I) present in the metallazo pigment A).

[0064] The pigment preparations according to the invention can be prepared by mixing at least one metallazo pigment A) with at least one aliphatic monocarboxylic acid B).

[0065] Mixing can be achieved mechanically, for example and preferably by stirring using suitable stirring devices such as slow-speed stirrers (e.g., blade, beam, planetary, or rotary mixers) or fast-speed stirrers (e.g., propeller, turbine, disc, or impeller stirrers). Mixing can also be achieved hydraulically by continuously circulating the reactor contents, e.g., using a centrifugal pump.

[0066] The metallazo pigment A) is usually mixed in the form of an aqueous suspension with at least one aliphatic monocarboxylic acid B). To prepare the aqueous suspension, at least one dried and optionally ground metallazo pigment A) is mixed with as much water as necessary to produce a complete suspension of the metallazo pigment.

[0067] However, the metallazo pigment A) can also preferably be used directly in the form of the aqueous reaction mixture as obtained during the synthesis of the metallazo pigment A).

[0068] To produce the pigment preparation according to the invention, an aqueous pigment suspension containing at least one metal azo pigment A) is admixed with at least one aliphatic monocarboxylic acid B) while stirring, preferably at a temperature in the range of 60 to 95°C, preferably within a period of 10 to 60 minutes, and the mixture thus prepared is stirred, preferably for 60 to 240 minutes. The pH of the mixture is then adjusted to a value between 3 and 7, and the pigment preparation is isolated using a suction filter or filter press.

[0069] The pigment preparation can be dried using conventional drying methods.

[0070] Possible drying processes include, for example, paddle drying or spray drying of corresponding aqueous slurries.

[0071] The pigment preparation can then be ground.

[0072] The pigment preparations according to the invention may contain one or more auxiliaries and / or additives.

[0073] In general, all auxiliaries and additives commonly used in pigment preparations can be considered as auxiliaries or additives, for example those from the series of surface-active agents such as dispersants, surfactants, wetting agents, emulsifiers, as well as bases and acids.

[0074] The present invention further provides a process for producing the pigment preparations according to the invention, which is characterized in that at least one metallazo pigment A) is mixed with at least one aliphatic monocarboxylic acid B) and optionally one or more auxiliaries and / or additives.

[0075] In general, the mixing ratio of aliphatic monocarboxylic acid B) to pigment A) in the pigment preparations according to the invention is 70 to 210 g, preferably 100 to 180 g and particularly preferably 120 to 160 g, in each case based on one mole of all metallazo compounds (I) contained in the metallazo pigment.

[0076] The pigment preparations according to the invention are surprisingly characterized by particularly good heat stability and also possess very good dispersibility. They are also characterized by high color strength. Chroma and transparency are excellently adjustable.

[0077] Unless otherwise stated, all heat stability values ​​refer to the measurement method according to European standard DIN EN 12877-2.

[0078] The pigment preparations according to the invention are ideally suited for all pigment applications.

[0079] The pigment preparations according to the invention are particularly suitable for the mass dyeing of synthetic, semi-synthetic or natural macromolecular substances, in particular polyvinyl chloride, polystyrene, polyamide, polyethylene or polypropylene, as well as for the spin dyeing of natural, regenerated or artificial fibers, such as cellulose, polyester, polycarbonate, polyacrylonitrile or polyamide fibers, and for printing textiles and paper.

[0080] The following examples are intended to illustrate the present invention without, however, limiting it thereto. Examples I. Production of metallazobarbituric acid-melamine pigments A to U according to the state of the art Example 1: Nickel azobarbituric acid-melamine pigment according to EP-A 26 82 435, Example 2 (Pigment A) a) Production of the raw pigment

[0081] 154.1 g (1.0 mol) of diazobarbituric acid and 128.1 g (1.0 mol) of barbituric acid were added to 3670 g of distilled water at 85°C. A pH of 5 was then adjusted with aqueous potassium hydroxide solution, and the reaction mixture was stirred for 90 minutes.

[0082] The azobarbituric acid thus prepared (1.0 mol) was treated with 5000 g of distilled water at 82°C.

[0083] Subsequently, a pH of 2 to 2.5 was adjusted by dropwise addition of 33 g of 30% hydrochloric acid. Then, 264.8 g (2.1 mol) of melamine were added. Subsequently, 1.0 mol of nickel chloride was added dropwise in the form of an approximately 25% solution. After 3 hours at 82°C, a pH of approximately 5.5 was adjusted by adding potassium hydroxide. b) Follow-up treatment

[0084] The mixture was then diluted with approximately 330 g of distilled water at 90°C. Then, 70 g of 30% hydrochloric acid were added dropwise, and the reaction mixture was stirred at 90°C for 12 hours. The pH of the reaction mixture was then adjusted to approximately 5 with aqueous potassium hydroxide solution. c) Reprocessing

[0085] The pigment was then isolated on a suction filter, washed, and dried at 80°C in a vacuum drying oven. It was then ground in a standard laboratory mill for approximately 2 minutes. (Pigment A) Examples 2 to 21: -Metallazobarbituric acid-melamine pigments B to U

[0086] The pigments B to U of Examples 2 to 21 listed in Table 1 below were prepared analogously to Example 1, but the 1.0 mol of nickel chloride was replaced in each case by mixtures of nickel chloride and copper(II) chloride and optionally a Me 2< metal chloride, in the molar amounts as indicated in Table 1. Determination of dispersion hardness

[0087] For pigments A to U, the dispersion hardness was determined as described in Procedure 1 below. The values ​​can be found in Table 1 Determination of heat resistance

[0088] For pigments A to U, heat resistance was determined as described in Procedure 2 below. The values ​​are shown in Table 1. Table 1: Pigments A to U Example pigment Ni [mol %] Cu [mol %] Me [mol %] Dispersing hardness Heat resistance at 300°C (DE) 1 A 100 0 0 100 5,1 2 B 99,95 0,05 0 101 5,0 3 C 99,9 0,1 0 103 5,2 4 D 99,7 0,3 0 102 4,9 5 E 99,5 0,5 0 103 5,2 6 F 99,0 1,0 0 103 5,1 7 G 98 2 0 99 5,3 8 H 97 3 0 101 5,3 9 I 95 5 0 34 5,5 10 J 85 15 0 38 4,9 11 K 70 30 0 50 5,3 12 L 50 50 0 62 5,2 13 M 25 75 0 70 5,5 14 N 5 95 0 72 4,9 15 O 2 98 0 76 5,3 16 P 1 99 0 76 5,2 17 Q 0,5 99,5 0 75 4,9 18 R 0,1 99,9 0 82 5,0 19 S 0,05 99,95 0 82 5,1 20 T 97 2 1 Zn 89 5,1 21 U 82 15 3 Co 53 5,2 II. Preparation of pigment preparations Example 22: Preparation of pigment preparation A-1 (not according to the invention)

[0089] An aqueous suspension of Pigment A, as obtained in step b) of Example 1, was mixed with 100 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation A-1) Examples 23 to 38: Preparation of pigment preparations A-2 to A-17 (not according to the invention)

[0090] In Examples 23 to 38, the non-inventive pigment preparations A-2 to A-17 were prepared analogously to Example 22. In each case, an aqueous suspension of pigment A as obtained after step b) of Example 1 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 2. Determination of dispersion hardness and heat resistance

[0091] For pigment preparations A-1 to A-17, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 2. Table 2: Pigment preparations with Pigment A Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 22 A-1 no 100 Pristerene 4910 90 5,1 23 A-2 no 50 Pristerene 4910 101 5,1 24 A-3 no 210 Pristerene 4910 88 5,1 25 A-4 no 150 Pristerene 4911 95 5,2 26 A-5 no 150 Pristerene 9429 93 5,0 27 A-6 no 100 Pristerene 4922 97 5,1 28 A-7 no 150 Caprylic acid 94 5,0 29 A-8 no 100 Capric acid 90 5,1 30 A-9 no 150 Lauric acid 96 5,0 31 A-10 no 210 Myristic acid 87 5,1 32 A-11 no 235 Palmitic acid 86 5,0 33 A-12 no 235 Stearic acid 85 4,9 34 A-13 no 150 Behenic acid 96 5,1 35 A-14 no 150 Lignoceric acid 95 5,2 36 A-15 no 70 oleic acid 102 5,1 37 A-16 no 150 Undecylenic acid 93 5,1 38 A-17 no 150 Nervonic acid 92 4,9 Example 39: Preparation of pigment preparation B-1 (not according to the invention)

[0092] An aqueous suspension of Pigment B, as obtained in step b) of Example 2, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation B-1) Examples 40 to 86: Preparation of pigment preparations B-2 to B-48 (not according to the invention)

[0093] In Examples 40 to 86, the non-inventive pigment preparations B-2 to B-48 were prepared analogously to Example 39. In each case, an aqueous suspension of pigment B as obtained after step b) of Example 2 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 3. Determination of dispersion hardness and heat resistance

[0094] For pigment preparations B-1 to B-48, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 3. Table 3: Pigment preparations with Pigment B Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 39 B-1 no 50 Pristerene 4910 91 5,0 40 B-2 no 100 Pristerene 4910 92 5,1 41 B-3 no 235 Pristerene 4910 92 5,0 42 B-4 no 50 Pristerene 4911 91 5,1 43 B-5 no 100 Pristerene 4911 101 4,9 44 B-6 no 235 Pristerene 4911 98 5,2 45 B-7 no 50 Pristerene 9429 89 5,1 46 B-8 no 70 Pristerene 9429 101 5,3 47 B-9 no 100 Pristerene 9429 100 5,2 48 B-10 no 210 Pristerene 9429 99 5,3 49 B-11 no 50 Pristerene 4922 93 4,9 50 B-12 no 100 Pristerene 4922 92 5,0 51 B-13 no 235 Pristerene 4922 89 5,3 52 B-14 no 50 Caprylic acid 95 5,2 53 B-15 no 235 Caprylic acid 97 4,9 54 B-16 no 70 Lignoceric acid 105 5,1 55 B-17 no 150 Lignoceric acid 104 5,0 56 B-18 no 70 Nervonic acid 110 4,9 57 B-19 no 210 Nervonic acid 112 4,9 58 B-20 no 50 Capric acid 98 5,0 59 B-21 no 210 Capric acid 99 5,2 60 B-22 no 235 Capric acid 98 5,3 61 B-23 no 50 Lauric acid 93 5,1 62 B-24 no 210 Lauric acid 93 4,9 63 B-25 no 235 Lauric acid 94 5,0 64 B-26 no 50 Myristic acid 89 4,9 65 B-27 no 100 Myristic acid 92 5,2 66 B-28 no 235 Myristic acid 94 5,1 67 B-29 no 50 Palmitic acid 96 5,1 68 B-30 no 100 Palmitic acid 101 5,0 69 B-31 no 210 Palmitic acid 100 5,2 70 B-32 no 235 Palmitic acid 99 5,1 71 B-33 no 50 Stearic acid 102 4,9 72 B-34 no 70 Stearic acid 101 5,2 73 B-35 no 210 Stearic acid 99 5,1 74 B-36 no 235 Stearic acid 102 5,1 75 B-37 no 50 Behenic acid 110 5,0 76 B-38 no 70 Behenic acid 112 5,1 77 B-39 no 210 Behenic acid 110 5,0 78 B-40 no 235 Behenic acid 112 5,2 79 B-41 no 50 oleic acid 98 5,1 80 B-42 no 150 oleic acid 96 5,0 81 B-43 no 210 oleic acid 98 5,2 82 B-44 no 235 oleic acid 95 5,1 83 B-45 no 50 Undecylenic acid 95 5,0 84 B-46 no 70 Undecylenic acid 98 5,1 85 B-47 no 210 Undecylenic acid 97 4,9 86 B-48 no 235 Undecylenic acid 95 5,1 Example 87: Preparation of pigment preparation C-1 (not according to the invention)

[0095] An aqueous suspension of Pigment C, as obtained after step b) of Example 3, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation C-1) Examples 88 to 143: Preparation of pigment preparations C-2 to C-57 (not according to the invention and according to the invention)

[0096] In Examples 88 to 143, pigment preparations C-2 to C-57, both non-inventive and inventive, were prepared analogously to Example 87. In each case, an aqueous suspension of pigment C as obtained after step b) of Example 3 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 4. Determination of dispersion hardness and heat resistance

[0097] For the pigment preparations C-1 to C-57, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 4 Table 4: Pigment preparations with Pigment C Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 87 C-1 no 50 Pristerene 4910 91 5,0 88 C-2 Yes 150 Pristerene 4910 15 1,0 89 C-3 Yes 210 Pristerene 4910 8 0,9 90 C-4 no 235 Pristerene 4910 18 4,4 91 C-5 no 50 Pristerene 4911 91 5,1 92 C-6 Yes 70 Pristerene 4911 14 1,0 93 C-7 Yes 210 Pristerene 4911 8 1,0 94 C-8 no 235 Pristerene 4911 10 4,6 95 C-9 no 50 Pristerene 9429 89 5,1 96 C-10 Yes 100 Pristerene 9429 14 1,1 97 C-11 Yes 150 Pristerene 9429 13 1,1 98 C-12 no 235 Pristerene 9429 14 4,8 99 C-13 no 50 Pristerene 4922 93 4,9 100 C-14 Yes 70 Pristerene 4922 15 1,0 101 C-15 Yes 210 Pristerene 4922 8 0,9 102 C-16 no 235 Pristerene 4922 10 4,4 103 C-17 no 50 Caprylic acid 56 4,5 104 C-18 no 150 Caprylic acid 54 4,8 105 C-19 no 235 Caprylic acid 45 4,9 106 C-20 no 150 Lignoceric acid 55 5,1 107 C-21 no 70 Lignoceric acid 68 5,0 108 C-22 no 210 Lignoceric acid 52 5,1 109 C-23 no 70 Nervonic acid 90 4,8 110 C-24 no 150 Nervonic acid 88 4,8 111 C-25 no 210 Nervonic acid 85 4,9 112 C-26 no 50 Capric acid 94 5,0 113 C-27 Yes 100 Capric acid 13 1,1 114 C-28 Yes 150 Capric acid 12 1,0 115 C-29 no 235 Capric acid 13 4,9 116 C-30 no 50 Lauric acid 91 5,1 117 C-31 Yes 70 Lauric acid 15 1,0 118 C-32 Yes 210 Lauric acid 8 0,9 119 C-33 no 235 Lauric acid 9 4,6 120 C-34 no 50 Myristic acid 89 4,9 121 C-35 Yes 70 Myristic acid 15 0,9 122 C-36 Yes 210 Myristic acid 9 0,9 123 C-37 no 235 Myristic acid 10 4,3 124 C-38 no 50 Palmitic acid 90 5,1 125 C-39 Yes 70 Palmitic acid 15 0,8 126 C-40 Yes 210 Palmitic acid 9 0,8 127 C-41 no 235 Palmitic acid 11 4,2 128 C-42 no 50 Stearic acid 88 4,9 129 C-43 Yes 70 Stearic acid 15 0,7 130 C-44 Yes 210 Stearic acid 7 0,6 131 C-45 no 235 Stearic acid 9 4,2 132 C-46 no 50 Behenic acid 91 5,0 133 C-47 Yes 70 Behenic acid 16 0,8 134 C-48 Yes 210 Behenic acid 9 0,9 135 C-49 no 235 Behenic acid 12 4,8 136 C-50 no 50 oleic acid 90 5,1 137 C-51 Yes 70 oleic acid 16 1,1 138 C-52 Yes 210 oleic acid 9 1,0 139 C-53 no 235 oleic acid 12 4,8 140 C-54 no 50 Undecylenic acid 88 5,0 141 C-55 Yes 70 Undecylenic acid 15 0,9 142 C-56 Yes 210 Undecylenic acid 10 0,9 143 C-57 no 235 Undecylenic acid 11 4,6 Example 144: Preparation of pigment preparation D-1 (not according to the invention)

[0098] An aqueous suspension of Pigment D, as obtained in step b) of Example 4, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation D-1) Examples 145 to 177: Preparation of pigment preparations D-2 to D-34 (not according to the invention and according to the invention)

[0099] In Examples 145 to 177, pigment preparations according to the invention and not according to the invention were prepared analogously to Example 144. In each case, an aqueous suspension of pigment D as obtained after step b) of Example 4 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 5. Determination of dispersion hardness and heat resistance

[0100] For pigment preparations D-1 to D-34, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 5 Table 5: Pigment preparations with Pigment D Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 144 D-1 no 50 Pristerene 4910 91 5,0 145 D-2 Yes 150 Pristerene 4910 7 0,4 146 D-3 Yes 210 Pristerene 4910 5 0,4 147 D-4 no 235 Pristerene 4910 9 4,6 148 D-5 no 50 Caprylic acid 56 4,5 149 D-6 no 150 Caprylic acid 55 4,9 150 D-7 no 235 Caprylic acid 49 4,9 151 D-8 no 70 Nervonic acid 90 4,8 152 D-9 no 150 Nervonic acid 89 5,0 153 D-10 no 210 Nervonic acid 86 4,9 154 D-11 no 50 Capric acid 94 5,0 155 D-12 Yes 100 Capric acid 10 0,6 156 D-13 Yes 150 Capric acid 8 0,5 157 D-14 no 235 Capric acid 12 4,6 158 D-15 no 50 Palmitic acid 90 5,1 159 D-16 Yes 70 Palmitic acid 6 0,3 160 D-17 Yes 210 Palmitic acid 5 0,3 161 D-18 no 235 Palmitic acid 7 4,2 162 D-19 no 50 Stearic acid 86 4,9 163 D-20 Yes 70 Stearic acid 6 0,4 164 D-21 Yes 210 Stearic acid 5 0,3 165 D-22 no 235 Stearic acid 8 4,6 166 D-23 no 50 Behenic acid 91 5,0 167 D-24 Yes 70 Behenic acid 8 0,5 168 D-25 Yes 210 Behenic acid 6 0,4 169 D-26 no 235 Behenic acid 10 4,8 170 D-27 no 50 oleic acid 90 5,1 171 D-28 Yes 70 oleic acid 8 0,6 172 D-29 Yes 210 oleic acid 7 0,5 173 D-30 no 235 oleic acid 11 4,9 174 D-31 no 50 Undecylenic acid 88 5,0 175 D-32 Yes 70 Undecylenic acid 7 0,4 176 D-33 Yes 210 Undecylenic acid 7 0,4 177 D-34 no 235 Undecylenic acid 9 4,9 Example 178: Preparation of pigment preparation E-1 (not according to the invention)

[0101] An aqueous suspension of Pigment E, as obtained in step b) of Example 5, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation E-1) Examples 179 to 259: Preparation of pigment preparations E-2 to E-81 (not according to the invention and according to the invention)

[0102] In Examples 179 to 259, pigment preparations E-2 to E-81 according to the invention and non-according to the invention were prepared analogously to Example 178. In each case, an aqueous suspension of pigment E as obtained after step b) of Example 5 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 6. Determination of dispersion hardness and heat resistance

[0103] For pigment preparations E-1 to E-81, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 6. Table 6: Pigment preparations with Pigment E Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 178 E-1 no 50 Pristerene 4910 91 5,0 179 E-2 Yes 70 Pristerene 4910 6 0,4 180 E-3 Yes 100 Pristerene 4910 6 0,4 181 E-4 Yes 150 Pristerene 4910 5 0,3 182 E-5 Yes 210 Pristerene 4910 5 0,4 183 E-6 no 235 Pristerene 4910 9 4,6 184 E-7 no 50 Pristerene 4911 91 5,1 185 E-8 Yes 70 Pristerene 4911 7 0,5 186 E-9 Yes 100 Pristerene 4911 6 0,5 187 E-19 Yes 150 Pristerene 4911 6 0,4 188 E-11 Yes 210 Pristerene 4911 5 0,5 189 E-12 no 235 Pristerene 4911 10 4,2 190 E-13 no 50 Pristerene 9429 89 5,1 191 E-14 Yes 70 Pristerene 9429 7 0,4 192 E-15 Yes 100 Pristerene 9429 7 0,4 193 E-16 Yes 150 Pristerene 9429 6 0,3 194 E-17 Yes 210 Pristerene 9429 6 0,5 195 E-18 no 235 Pristerene 9429 9 4,6 196 E-19 no 50 Pristerene 4922 93 4,9 197 E-20 Yes 70 Pristerene 4922 7 0,5 199 E-21 Yes 100 Pristerene 4922 7 0,5 200 E-22 Yes 150 Pristerene 4922 7 0,4 201 E-23 Yes 210 Pristerene 4922 6 0,5 202 E-24 no 235 Pristerene 4922 8 4,3 203 E-25 no 50 Caprylic acid 56 4,5 204 E-26 no 150 Caprylic acid 54 4,8 205 E-27 no 235 Caprylic acid 45 4,9 206 E-28 no 150 Lignoceric acid 55 5,1 207 E-29 no 70 Lignoceric acid 68 5,0 208 E-30 no 210 Lignoceric acid 52 5,1 209 E-31 no 70 Nervonic acid 90 4,8 210 E-32 no 150 Nervonic acid 88 4,8 211 E-33 no 210 Nervonic acid 85 4,9 212 E-34 no 50 Capric acid 94 5,0 213 E-35 Yes 70 Capric acid 9 0,6 214 E-36 Yes 100 Capric acid 9 0,6 215 E-37 Yes 150 Capric acid 8 0,5 216 E-38 Yes 210 Capric acid 8 0,6 217 E-39 no 235 Capric acid 10 4,6 218 E-40 no 50 Lauric acid 91 5,1 219 E-41 Yes 70 Lauric acid 9 0,5 220 E-42 Yes 100 Lauric acid 9 0,5 221 E-43 Yes 150 Lauric acid 9 0,4 222 E-44 Yes 210 Lauric acid 8 0,5 223 E-45 no 235 Lauric acid 10 4,8 224 E-46 no 50 Myristic acid 89 4,9 225 E-47 Yes 70 Myristic acid 8 0,5 226 E-48 Yes 100 Myristic acid 8 0,5 227 E-49 Yes 150 Myristic acid 7 0,5 228 E-50 Yes 210 Myristic acid 7 0,6 229 E-51 no 235 Myristic acid 11 4,3 230 E-52 no 50 Palmitic acid 90 5,1 231 E-53 Yes 70 Palmitic acid 6 0,4 232 E-54 Yes 100 Palmitic acid 6 0,4 233 E-55 Yes 150 Palmitic acid 5 0,3 234 E-56 Yes 210 Palmitic acid 5 0,4 235 E-56 no 235 Palmitic acid 9 4,3 236 E-58 no 50 Stearic acid 88 4,9 237 E-59 Yes 70 Stearic acid 6 0,3 238 E-60 Yes 100 Stearic acid 5 0,3 239 E-61 Yes 150 Stearic acid 5 0,4 240 E-62 Yes 210 Stearic acid 4 0,4 241 E-63 no 235 Stearic acid 8 4,5 242 E-64 no 50 Behenic acid 91 5,0 243 E-65 Yes 70 Behenic acid 8 0,5 244 E-66 Yes 100 Behenic acid 8 0,5 245 E-67 Yes 150 Behenic acid 7 0,4 246 E-68 Yes 210 Behenic acid 7 0,5 247 E-69 no 235 Behenic acid 9 4,6 248 E-70 no 50 oleic acid 90 5,1 249 E-71 Yes 70 oleic acid 9 0,6 250 E-72 Yes 100 oleic acid 8 0,6 251 E-73 Yes 150 oleic acid 8 0,5 252 E-74 Yes 210 oleic acid 7 0,6 253 E-75 no 235 oleic acid 12 4,3 254 E-76 no 50 Undecylenic acid 88 5,0 255 E-77 Yes 70 Undecylenic acid 8 0,5 256 E-78 Yes 100 Undecylenic acid 8 0,5 257 E-79 Yes 150 Undecylenic acid 7 0,6 258 E-80 Yes 210 Undecylenic acid 7 0,6 259 E-81 no 235 Undecylenic acid 10 4,2 Example 260: Preparation of pigment preparation F-1 (not according to the invention)

[0104] An aqueous suspension of Pigment F, as obtained in step b) of Example 6, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation F-1) Examples 261 to 293: Preparation of pigment preparations F-2 to F-33 (not according to the invention and according to the invention)

[0105] In Examples 261 to 293, pigment preparations F-2 to F-33 according to the invention and non-according to the invention were prepared analogously to Example 260. In each case, an aqueous suspension of pigment F as obtained after step b) of Example 6 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 7. Determination of dispersion hardness and heat resistance

[0106] For the pigment preparations F-1 to F-33, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 7 Table 7: Pigment preparations with Pigment F Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 260 F-1 no 50 Pristerene 4910 90 5,0 261 F-2 Yes 100 Pristerene 4910 3 0,2 262 F-3 Yes 210 Pristerene 4910 3 0,1 263 F-4 no 235 Pristerene 4910 5 4,1 264 F-5 no 50 Caprylic acid 56 4,5 265 F-6 no 150 Caprylic acid 56 4,9 266 F-7 no 235 Caprylic acid 48 4,9 267 F-8 no 70 Nervonic acid 91 4,8 268 F-9 no 150 Nervonic acid 88 5,0 269 F-10 no 210 Nervonic acid 86 4,9 270 F-11 no 50 Capric acid 94 5,0 271 F-12 Yes 100 Capric acid 3 0,2 272 F-13 Yes 150 Capric acid 2 0,2 273 F-14 no 235 Capric acid 6 4,1 274 F-15 no 50 Palmitic acid 90 5,1 275 F-16 Yes 70 Palmitic acid 2 0,1 276 F-17 Yes 210 Palmitic acid 2 0,1 277 F-18 no 235 Palmitic acid 5 3,9 278 F-19 no 50 Stearic acid 86 4,9 279 F-20 Yes 70 Stearic acid 2 0,1 280 F-21 Yes 210 Stearic acid 2 0,1 281 F-22 no 235 Stearic acid 6 4,2 282 F-23 no 50 Behenic acid 91 5,0 283 F-24 Yes 70 Behenic acid 3 0,2 284 F-25 Yes 210 Behenic acid 2 0,2 285 F-26 no 235 Behenic acid 14 4,1 286 F-27 no 50 oleic acid 3 0,2 287 F-28 Yes 70 oleic acid 2 0,2 288 F-29 Yes 210 oleic acid 2 0,2 289 F-30 no 235 oleic acid 6 4,3 290 F-30 no 50 Undecylenic acid 88 5,0 291 F-31 Yes 70 Undecylenic acid 3 0,2 292 F-32 Yes 210 Undecylenic acid 2 0,3 293 F-33 no 235 Undecylenic acid 6 4,5 Example 294: Preparation of pigment preparation G-1 (not according to the invention)

[0107] An aqueous suspension of Pigment G, as obtained in step b) of Example 7, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation G-1) Examples 295 to 374: Preparation of pigment preparations G-2 to G-81 (not according to the invention and according to the invention)

[0108] In Examples 295 to 374, pigment preparations G-2 to G-81 according to the invention and non-according to the invention were prepared analogously to Example 294. In each case, an aqueous suspension of pigment G as obtained after step b) of Example 7 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 8. Determination of dispersion hardness and heat resistance

[0109] For the pigment preparations G-1 to G-81, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 8 Table 8: Pigment preparations with Pigment G Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 294 G-1 No 50 Pristerene 4910 70 5,3 295 G-2 Yes 70 Pristerene 4910 3 0,1 296 G-3 Yes 100 Pristerene 4910 3 0,1 297 G-4 Yes 150 Pristerene 4910 2 0,1 298 G-5 Yes 210 Pristerene 4910 2 0,1 299 G-6 no 235 Pristerene 4910 5 4,5 300 G-7 no 50 Pristerene 4911 72 5,3 301 G-8 Yes 70 Pristerene 4911 3 0,2 302 G-9 Yes 100 Pristerene 4911 3 0,2 303 G-10 Yes 150 Pristerene 4911 3 0,1 304 G-11 Yes 210 Pristerene 4911 2 0,1 305 G-12 no 235 Pristerene 4911 6 4,6 306 G-13 no 50 Pristerene 9429 70 5,5 307 G-14 Yes 70 Pristerene 9429 4 0,2 308 G-15 Yes 100 Pristerene 9429 4 0,2 309 G-16 Yes 150 Pristerene 9429 4 0,1 310 G-17 Yes 210 Pristerene 9429 3 0,1 311 G-18 no 235 Pristerene 9429 7 4,6 312 G-19 no 50 Pristerene 4922 82 5,2 313 G-20 Yes 70 Pristerene 4922 3 0,2 314 G-21 Yes 100 Pristerene 4922 3 0,2 315 G-22 Yes 150 Pristerene 4922 3 0,2 316 G-23 Yes 210 Pristerene 4922 2 0,3 317 G-24 no 235 Pristerene 4922 6 4,5 318 G-25 no 50 Caprylic acid 56 5,2 319 G-26 no 150 Caprylic acid 59 5,2 320 G-27 no 235 Caprylic acid 46 5,1 321 G-28 no 150 Lignoceric acid 54 4,9 322 G-29 no 70 Lignoceric acid 70 4,9 323 G-30 no 210 Lignoceric acid 53 5,1 324 G-31 no 70 Nervonic acid 88 4,8 325 G-32 no 150 Nervonic acid 85 4,8 326 G-33 no 210 Nervonic acid 84 4,9 327 G-34 no 50 Capric acid 73 5,3 328 G-35 Yes 70 Capric acid 5 0,3 329 G-36 Yes 100 Capric acid 5 0,2 330 G-37 Yes 150 Capric acid 4 0,3 331 G-38 Yes 210 Capric acid 4 0,3 332 G-39 no 235 Capric acid 8 4,5 333 G-40 no 50 Lauric acid 70 5,3 334 G-41 Yes 70 Lauric acid 4 0,2 335 G-42 Yes 100 Lauric acid 4 0,2 336 G-43 Yes 150 Lauric acid 4 0,2 337 G-44 Yes 210 Lauric acid 3 0,3 338 G-45 no 235 Lauric acid 8 4,4 339 G-46 no 50 Myristic acid 71 5,2 340 G-47 Yes 70 Myristic acid 4 0,1 341 G-48 Yes 100 Myristic acid 4 0,1 342 G-49 Yes 150 Myristic acid 3 0,2 343 G-50 Yes 210 Myristic acid 3 0,2 344 G-51 no 235 Myristic acid 8 4,2 345 G-52 no 50 Palmitic acid 69 5,3 346 G-53 Yes 70 Palmitic acid 3 0,1 347 G-54 Yes 100 Palmitic acid 3 0,1 348 G-55 Yes 150 Palmitic acid 2 0,1 349 G-56 Yes 210 Palmitic acid 2 0,2 350 G-57 no 235 Palmitic acid 5 4,1 351 G-58 no 50 Stearic acid 68 5,2 352 G-59 Yes 70 Stearic acid 2 0,1 353 G-60 Yes 100 Stearic acid 2 0,1 354 G-61 Yes 150 Stearic acid 2 0,1 355 G-62 Yes 210 Stearic acid 2 0,2 356 G-63 no 235 Stearic acid 4 4,1 357 G-64 no 50 Behenic acid 75 5,3 358 G-65 Yes 70 Behenic acid 4 0,2 359 G-66 Yes 100 Behenic acid 4 0,2 360 G-67 Yes 150 Behenic acid 3 0,2 361 G-68 Yes 210 Behenic acid 3 0,3 362 G-69 no 235 Behenic acid 6 4,3 363 G-70 no 50 oleic acid 69 5,2 364 G-71 Yes 70 oleic acid 5 0,2 365 G-72 Yes 100 oleic acid 5 0,2 366 G-73 Yes 150 oleic acid 4 0,2 367 G-74 Yes 210 oleic acid 4 0,3 368 G-75 no 235 oleic acid 9 4,4 369 G-76 no 50 Undecylenic acid 73 5,1 370 G-77 Yes 70 Undecylenic acid 4 0,2 371 G-78 Yes 100 Undecylenic acid 4 0,2 372 G-79 Yes 150 Undecylenic acid 4 0,3 373 G-80 Yes 210 Undecylenic acid 3 0,3 374 G-81 no 235 Undecylenic acid 8 4,3 Example 375: Preparation of pigment preparation H-1 (not according to the invention)

[0110] An aqueous suspension of Pigment H, as obtained after step b) of Example 8, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation H-1) Examples 376 to 406: Preparation of pigment preparations H-2 to H-35 (not according to the invention and according to the invention)

[0111] In Examples 376 to 406, pigment preparations H-2 to H-35 according to the invention and non-according to the invention were prepared analogously to Example 375. In each case, an aqueous suspension of pigment H as obtained after step b) of Example 8 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 9. Determination of dispersion hardness and heat resistance

[0112] For pigment preparations H-1 to H-35, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 9. Table 9: Pigment preparations with Pigment H Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 375 H-1 no 50 Pristerene 4910 69 5,0 376 H-2 Yes 100 Pristerene 4910 3 0,2 377 H-3 Yes 210 Pristerene 4910 3 0,2 378 H-4 no 235 Pristerene 4910 7 4,1 379 H-5 no 150 Caprylic acid 57 4,9 380 H-6 no 210 Caprylic acid 51 5,1 381 H-7 no 150 Nervonic acid 89 5,3 382 H-8 no 210 Nervonic acid 85 5,1 383 H-9 no 50 Capric acid 92 5,0 384 H-10 Yes 100 Capric acid 3 0,2 385 H-11 Yes 150 Capric acid 4 0,2 386 H-12 no 235 Capric acid 9 4,2 387 H-13 no 50 Palmitic acid 90 5,1 388 H-14 Yes 70 Palmitic acid 3 0,1 389 H-15 Yes 210 Palmitic acid 3 0,2 390 H-16 no 235 Palmitic acid 7 4,2 391 H-17 no 50 Stearic acid 85 4,9 392 H-18 Yes 70 Stearic acid 3 0,1 393 H-19 Yes 210 Stearic acid 3 0,2 394 H-20 no 235 Stearic acid 8 4,2 395 H-21 no 50 Behenic acid 90 5,0 396 H-22 Yes 70 Behenic acid 4 0,3 397 H-23 Yes 210 Behenic acid 4 0,3 398 H-24 no 235 Behenic acid 8 4,1 399 H-25 no 50 oleic acid 89 5,1 400 H-26 Yes 70 oleic acid 5 0,3 401 H-27 Yes 210 oleic acid 4 0,3 402 H-28 no 235 oleic acid 9 4,6 403 H-29 no 50 Undecylenic acid 88 5,0 404 H-30 Yes 70 Undecylenic acid 4 0,3 405 H-31 Yes 210 Undecylenic acid 4 0,3 406 H-32 no 235 Undecylenic acid 13 4,3 Example 407: Preparation of pigment preparation I-1 (not according to the invention)

[0113] An aqueous suspension of Pigment I, as obtained in step b) of Example 9, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation I-1) Examples 408 to 438: Preparation of pigment preparations I-2 to I-32 (not according to the invention and according to the invention)

[0114] In Examples 408 to 438, pigment preparations I-2 to I-32 according to the invention and not according to the invention were prepared analogously to Example 407. In each case, an aqueous suspension of pigment I as obtained after step b) of Example 9 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 10. Determination of dispersion hardness and heat resistance

[0115] For pigment preparations I-1 to I-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 10. Table 10: Pigment preparations with Pigment I Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 407 I-1 no 50 Pristerene 4910 33 5,0 408 I-2 Yes 100 Pristerene 4910 4 0,2 409 I-3 Yes 210 Pristerene 4910 4 0,2 410 I-4 no 235 Pristerene 4910 6 4,5 411 I-5 no 150 Caprylic acid 35 4,9 412 I-6 no 210 Caprylic acid 34 5,1 413 I-7 no 150 Nervonic acid 36 5,3 414 I-8 no 210 Nervonic acid 34 5,1 415 I-9 no 50 Capric acid 34 5,0 416 I-10 Yes 100 Capric acid 5 0,3 417 I-11 Yes 150 Capric acid 5 0,3 418 I-12 no 235 Capric acid 4 4,8 419 I-13 no 50 Palmitic acid 36 5,1 420 I-14 Yes 70 Palmitic acid 4 0,2 421 I-15 Yes 210 Palmitic acid 4 0,2 422 I-16 no 235 Palmitic acid 7 4,5 423 I-17 no 50 Stearic acid 33 4,9 424 I-18 Yes 150 Stearic acid 4 0,1 425 I-19 Yes 210 Stearic acid 3 0,2 426 I-20 no 235 Stearic acid 6 4,9 427 I-21 no 50 Behenic acid 38 5,0 428 I-22 Yes 70 Behenic acid 5 0,3 429 I-23 Yes 210 Behenic acid 4 0,3 430 I-24 no 235 Behenic acid 8 4,5 431 I-25 no 50 oleic acid 40 5,1 432 I-26 Yes 70 oleic acid 5 0,3 433 I-27 Yes 210 oleic acid 5 0,3 434 I-28 no 235 oleic acid 9 4,8 435 I-29 no 50 Undecylenic acid 42 5,0 436 I-30 Yes 70 Undecylenic acid 4 0,2 437 I-31 Yes 210 Undecylenic acid 5 0,2 438 I-32 no 235 Undecylenic acid 9 4,9 Example 439: Preparation of pigment preparation J-1 (not according to the invention)

[0116] An aqueous suspension of Pigment I, as obtained in step b) of Example 10, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation J-1) Examples 440 to 469: Preparation of pigment preparations J-2 to J-32 (not according to the invention and according to the invention)

[0117] In Examples 408 to 438, pigment preparations I-2 to I-32 according to the invention and not according to the invention were prepared analogously to Example 407. In each case, an aqueous suspension of pigment J as obtained after step b) of Example 10 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 11. Determination of dispersion hardness and heat resistance

[0118] For pigment preparations J-1 to J-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 11. Table 11: Pigment preparations with Pigment J Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 439 J-1 no 50 Pristerene 4910 37 5,0 440 J-2 Yes 100 Pristerene 4910 7 0,4 441 J-3 Yes 210 PrJsterene 4910 6 0,4 442 J-4 no 235 Pristerene 4910 9 4,6 443 J-5 no 150 Caprylic acid 41 4,9 444 J-6 no 210 Caprylic acid 42 5,1 445 J-7 no 150 Nervonic acid 40 5,3 446 J-8 no 210 Nervonic acid 39 5,1 447 J-9 no 50 Capric acid 36 5,0 448 J-10 Yes 100 Capric acid 8 0,5 449 J-11 Yes 150 Capric acid 8 0,4 450 J-12 no 235 Capric acid 11 4,2 451 J-13 no 50 Palmitic acid 38 5,2 452 J-14 Yes 70 Palmitic acid 7 0,4 453 J-15 Yes 210 Palmitic acid 6 0,4 454 J-16 no 235 Palmitic acid 10 4,6 455 J-17 no 50 Stearic acid 39 4,9 456 J-18 Yes 150 Stearic acid 6 0,3 457 J-19 Yes 210 Stearic acid 6 0,3 458 J-20 no 235 Stearic acid 9 4,6 459 J-21 no 50 Behenic acid 40 5,0 460 J-22 Yes 70 Behenic acid 8 0,5 461 J-23 Yes 210 Behenic acid 8 0,6 462 J-24 no 235 Behenic acid 12 4,3 463 J-25 no 50 oleic acid 45 5,1 464 J-26 Yes 70 oleic acid 9 0,5 465 J-27 Yes 210 oleic acid 8 0,5 466 J-28 no 235 oleic acid 11 4,9 467 J-29 no 50 Undecylenic acid 48 5,0 468 J-30 Yes 70 Undecylenic acid 8 0,6 468 J-31 Yes 210 Undecylenic acid 8 0,5 469 J-32 no 235 Undecylenic acid 11 4,9 Example 470: Preparation of pigment preparation K-1 (not according to the invention)

[0119] An aqueous suspension of Pigment K as obtained in step b) of Example 11 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation K-1) Examples 471 to 501: Preparation of pigment preparations K-2 to K-32 (not according to the invention and according to the invention)

[0120] In Examples 408 to 438, pigment preparations K-2 to K-32 according to the invention and non-according to the invention were prepared analogously to Example 470. In each case, an aqueous suspension of pigment K as obtained after step b) of Example 11 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 12. Determination of dispersion hardness and heat resistance

[0121] For pigment preparations K-1 to K-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 12. Table 12: Pigment preparations with pigment K Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 470 K-1 no 50 Pristerene 4910 49 5,1 471 K-2 Yes 70 Pristerene 4910 9 0,5 472 K-3 Yes 210 Pristerene 4910 8 0,6 473 K-4 no 235 Pristerene 4910 11 4,5 474 K-5 no 100 Caprylic acid 51 5,2 475 K-6 no 210 Caprylic acid 52 5,3 476 K-7 no 70 Nervonic acid 48 5,4 477 K-8 no 210 Nervonic acid 48 5,1 478 K-9 no 50 Myristic acid 48 5,2 479 K-10 Yes 100 Myristic acid 10 0,6 480 K-11 Yes 210 Myristic acid 9 0,6 481 K-12 no 235 Myristic acid 13 4,6 482 K-13 no 50 Palmitic acid 45 5,2 483 K-14 Yes 100 Palmitic acid 9 0,5 484 K-15 Yes 210 Palmitic acid 8 0,5 485 K-16 no 235 Palmitic acid 12 4,7 486 K-17 no 50 Stearic acid 43 5,2 487 K-18 Yes 70 Stearic acid 8 0,5 488 K-19 Yes 210 Stearic acid 8 0,5 489 K-20 no 235 Stearic acid 11 4,8 490 K-21 no 50 Behenic acid 44 5,1 491 K-22 Yes 150 Behenic acid 9 0,6 492 K-23 Yes 210 Behenic acid 8 0,6 493 K-24 no 235 Behenic acid 12 4,9 494 K-25 no 50 oleic acid 48 5,1 495 K-26 Yes 70 oleic acid 10 0,6 496 K-27 Yes 210 oleic acid 10 0,6 497 K-28 no 235 oleic acid 13 4,9 498 K-29 no 50 Undecylenic acid 52 5,2 499 K-30 Yes 70 Undecylenic acid 9 0,5 500 K-31 Yes 210 Undecylenic acid 9 0,6 501 K-32 no 235 Undecylenic acid 14 5,1 Example 502: Preparation of pigment preparation L-1 (not according to the invention)

[0122] An aqueous suspension of Pigment L as obtained in step b) of Example 12 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation L-1) Examples 503 to 533: Preparation of pigment preparations L-2 to L-32 (not according to the invention and according to the invention)

[0123] In Examples 503 to 533, pigment preparations L-2 to L-32 according to the invention and non-according to the invention were prepared analogously to Example 502. In each case, an aqueous suspension of pigment L as obtained after step b) of Example 12 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 13. Determination of dispersion hardness and heat resistance

[0124] For pigment preparations L-1 to L-32, the dispersion hardness and heat resistance were determined according to the procedures 1 and 2 below. The values ​​can also be found in Table 13 Table 13: Pigment preparations with Pigment L Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 502 L-1 no 50 Pristerene 4910 60 5,1 503 L-2 Yes 100 Pristerene 4910 11 0,7 504 L-3 Yes 210 Pristerene 4910 12 0,7 505 L-4 no 235 Pristerene 4910 13 4,6 506 L-5 no 70 Caprylic acid 59 5,2 507 L-6 no 210 Caprylic acid 58 5,3 508 L-7 no 70 Nervonic acid 53 5,3 509 L-8 no 210 Nervonic acid 55 5,2 510 L-9 no 50 Myristic acid 52 5,2 511 L-10 Yes 100 Myristic acid 12 0,8 512 L-11 Yes 150 Myristic acid 11 0,7 513 L-12 no 235 Myristic acid 22 4,5 514 L-13 no 50 Palmitic acid 56 5,2 515 L-14 Yes 150 Palmitic acid 9 0,7 516 L-15 Yes 210 Palmitic acid 9 0,7 517 L-16 no 235 Palmitic acid 13 4,7 518 L-17 no 50 Stearic acid 55 5,2 519 L-18 Yes 100 Stearic acid 9 0,7 520 L-19 Yes 210 Stearic acid 8 0,7 521 L-20 no 235 Stearic acid 13 4,6 522 L-21 no 50 Behenic acid 58 5,1 523 L-22 Yes 150 Behenic acid 11 0,8 524 L-23 Yes 210 Behenic acid 10 0,7 525 L-24 no 235 Behenic acid 16 4,9 526 L-25 no 50 oleic acid 60 5,1 527 L-26 Yes 70 oleic acid 12 0,8 528 L-27 Yes 210 oleic acid 11 0,9 529 L-28 no 235 oleic acid 16 4,8 530 L-29 no 50 Undecylenic acid 58 5,2 531 L-30 Yes 100 Undecylenic acid 11 0,8 532 L-31 Yes 210 Undecylenic acid 10 0,8 533 L-32 no 235 Undecylenic acid 16 5,0 Example 534: Preparation of pigment preparation M-1 (not according to the invention)

[0125] An aqueous suspension of Pigment M as obtained in step b) of Example 13 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation M-1) Examples 535 to 565: Preparation of pigment preparations M-2 to M-32 (not according to the invention and according to the invention)

[0126] In Examples 535 to 565, pigment preparations M-2 to M-32 according to the invention and non-according to the invention were prepared analogously to Example 470. In each case, an aqueous suspension of the pigment M as obtained after step b) of Example 13 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 14. Determination of dispersion hardness and heat resistance

[0127] For pigment preparations M-1 to M-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 14. Table 14: Pigment preparations with Pigment M Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 534 M-1 no 50 Pristerene 4910 68 5,1 535 M-2 Yes 100 Pristerene 4910 13 0,8 536 M-3 Yes 210 Pristerene 4910 12 0,9 537 M-4 no 235 Pristerene 4910 18 4,6 538 M-5 no 70 Caprylic acid 65 5,1 539 M-6 no 210 Caprylic acid 69 5,2 540 M-7 no 70 Nervonic acid 71 5,2 541 M-8 no 210 Nervonic acid 73 5,3 542 M-9 no 50 Myristic acid 65 5,2 543 M-10 Yes 100 Myristic acid 14 0,9 544 M-11 Yes 150 Myristic acid 13 0,8 545 M-12 no 235 Myristic acid 21 4,6 546 M-13 no 50 Palmitic acid 66 5,1 547 M-14 Yes 150 Palmitic acid 12 0,8 548 M-15 Yes 210 Palmitic acid 11 0,9 549 M-16 no 235 Palmitic acid 18 4,8 550 M-17 no 50 Stearic acid 67 5,0 551 M-18 Yes 100 Stearic acid 12 0,8 552 M-19 Yes 210 Stearic acid 11 0,8 553 M-20 no 235 Stearic acid 16 4,9 554 M-21 no 50 Behenic acid 66 5,1 555 M-22 Yes 150 Behenic acid 14 0,9 556 M-23 Yes 210 Behenic acid 13 0,9 557 M-24 no 235 Behenic acid 22 4,8 558 M-25 no 50 oleic acid 69 5,1 559 M-26 Yes 70 oleic acid 15 0,8 560 M-27 Yes 210 oleic acid 14 0,9 561 M-28 no 235 oleic acid 24 4,9 562 M-29 no 50 Undecylenic acid 66 5,2 563 M-30 Yes 100 Undecylenic acid 13 0,9 564 M-31 Yes 210 Undecylenic acid 12 0,9 565 M-32 no 235 Undecylenic acid 16 5,0 Example 566: Preparation of pigment preparation N-1 (not according to the invention)

[0128] An aqueous suspension of Pigment N, as obtained in step b) of Example 14, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation N-1) Examples 567 to 597: Preparation of pigment preparations N-2 to N-32 (not according to the invention and according to the invention)

[0129] In Examples 568 to 597, pigment preparations N-2 to N-32 according to the invention and not according to the invention were prepared analogously to Example 567. In each case, an aqueous suspension of pigment N as obtained after step b) of Example 14 was admixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as indicated in Table 15. Determination of dispersion hardness and heat resistance

[0130] For pigment preparations N-1 to N-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 15. Table 15: Pigment preparations with Pigment N Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 566 N-1 no 50 Pristerene 4910 70 5,1 567 N-2 Yes 100 Pristerene 4910 14 0,9 568 N-3 Yes 210 Pristerene 4910 14 0,9 569 N-4 no 235 Pristerene 4910 19 4,7 570 N-5 no 70 Caprylic acid 66 5,0 571 N-6 no 210 Caprylic acid 65 5,3 572 N-7 no 70 Nervonic acid 70 5,3 573 N-8 no 210 Nervonic acid 71 5,1 574 N-9 no 50 Myristic acid 66 5,1 575 N-10 Yes 100 Myristic acid 15 1,0 576 N-11 Yes 150 Myristic acid 15 1,0 577 N-12 no 235 Myristic acid 23 4,9 578 N-13 no 50 Palmitic acid 68 5,1 579 N-14 Yes 150 Palmitic acid 13 0,9 580 N-15 Yes 210 Palmitic acid 13 0,8 581 N-16 no 235 Palmitic acid 19 4,9 582 N-17 no 50 Stearic acid 65 5,1 583 N-18 Yes 100 Stearic acid 13 0,9 584 N-19 Yes 210 Stearic acid 12 0,8 585 N-20 no 235 Stearic acid 20 4,9 586 N-21 no 50 Behenic acid 67 5,1 587 N-22 Yes 150 Behenic acid 15 0,9 588 N-23 Yes 210 Behenic acid 14 0,9 589 N-24 no 235 Behenic acid 23 4,9 590 N-25 no 50 oleic acid 70 5,1 591 N-26 Yes 70 oleic acid 15 1,0 592 N-27 Yes 210 oleic acid 15 1,0 593 N-28 no 235 oleic acid 27 4,8 594 N-29 no 50 Undecylenic acid 68 5,2 595 N-30 Yes 100 Undecylenic acid 14 0,9 596 N-31 Yes 210 Undecylenic acid 14 0,9 597 N-32 no 235 Undecylenic acid 28 4,9 Example 598: Preparation of pigment preparation O-1 (not according to the invention)

[0131] An aqueous suspension of Pigment O as obtained in step b) of Example 11 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation O-1) Examples 599 to 629: Preparation of pigment preparations O-2 to O-32 (not according to the invention and according to the invention)

[0132] Analogous to Example 598, in the examples 599 to 629Inventive and non-inventive pigment preparations O-2 to O-32 were prepared. In each case, an aqueous suspension of the pigment O as obtained after step b) of Example 15 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 16. Determination of dispersion hardness and heat resistance

[0133] For pigment preparations O-1 to O-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 16. Table 16: Pigment preparations with Pigment O Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 598 O-1 no 50 Pristerene 4910 75 5,1 599 O-2 Yes 100 Pristerene 4910 14 1,0 600 O-3 Yes 210 Pristerene 4910 13 0,9 601 O-4 no 235 Pristerene 4910 18 4,7 602 O-5 no 70 Caprylic acid 74 5,2 603 O-6 no 210 Caprylic acid 71 5,3 604 O-7 no 70 Nervonic acid 73 5,1 605 O-8 no 210 Nervonic acid 72 5,0 606 O-9 no 50 Myristic acid 74 5,3 607 O-10 Yes 100 Myristic acid 13 1,0 608 O-11 Yes 150 Myristic acid 11 0,9 609 O-12 no 235 Myristic acid 14 4,9 610 O-13 no 50 Palmitic acid 72 5,1 611 O-14 Yes 150 Palmitic acid 12 1,0 612 O-15 Yes 210 Palmitic acid 9 0,9 613 O-16 no 235 Palmitic acid 12 4,9 614 O-17 no 50 Stearic acid 70 5,0 615 O-18 Yes 100 Stearic acid 12 0,9 616 O-19 Yes 210 Stearic acid 11 0,8 617 O-20 no 235 Stearic acid 14 4,8 618 O-21 no 50 Behenic acid 73 5,0 619 O-22 Yes 150 Behenic acid 13 0,9 620 O-23 Yes 210 Behenic acid 12 0,8 621 O-24 no 235 Behenic acid 16 4,9 622 O-25 no 50 oleic acid 73 5,1 623 O-26 Yes 70 oleic acid 14 0,9 624 O-27 Yes 210 oleic acid 12 0,9 625 O-28 no 235 oleic acid 18 5,1 626 O-29 no 50 Undecylenic acid 74 5,2 627 O-30 Yes 100 Undecylenic acid 14 0,9 628 O-31 Yes 210 Undecylenic acid 12 0,9 629 O-32 no 235 Undecylenic acid 15 5,1 Example 630: Preparation of pigment preparation P-1 (not according to the invention)

[0134] An aqueous suspension of pigment P as obtained in step b) of Example 16 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation P-1) Examples 631 to 661: Preparation of pigment preparations P-2 to P-32 (not according to the invention and according to the invention)

[0135] Analogous to Example 630, in the examples 631 to 661Inventive and non-inventive pigment preparations P-2 to P-32 were prepared. In each case, an aqueous suspension of the pigment P as obtained after step b) of Example 16 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 17. Determination of dispersion hardness and heat resistance

[0136] For pigment preparations P-1 to P-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 17. Table 17: Pigment preparations with Pigment P Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 630 P-1 no 50 Pristerene 4910 74 5,1 631 P-2 Yes 100 Pristerene 4910 14 0,9 632 P-3 Yes 210 Pristerene 4910 12 0,9 633 P-4 no 235 Pristerene 4910 19 4,6 634 P-5 no 70 Caprylic acid 74 5,1 635 P-6 no 210 Caprylic acid 71 5,2 636 P-7 no 70 Nervonic acid 73 5,2 637 P-8 no 210 Nervonic acid 72 5,3 638 P-9 no 50 Myristic acid 74 5,2 639 P-10 Yes 100 Myristic acid 14 1,0 640 P-11 Yes 150 Myristic acid 13 1,1 641 P-12 no 235 Myristic acid 20 4,8 642 P-13 no 50 Palmitic acid 72 5,1 643 P-14 Yes 150 Palmitic acid 14 0,9 644 P-15 Yes 210 Palmitic acid 13 0,9 645 P-16 no 235 Palmitic acid 19 4,8 646 P-17 no 50 Stearic acid 70 5,0 647 P-18 Yes 100 Stearic acid 13 1,0 648 P-19 Yes 210 Stearic acid 11 1,0 649 P-20 no 235 Stearic acid 18 4,9 650 P-21 no 50 Behenic acid 73 5,1 651 P-22 Yes 150 Behenic acid 13 1,0 652 P-23 Yes 210 Behenic acid 10 0,9 653 P-24 no 235 Behenic acid 16 4,8 654 P-25 no 50 oleic acid 73 5,1 655 P-26 Yes 70 oleic acid 14 1,0 656 P-27 Yes 210 oleic acid 12 0,9 657 P-28 no 235 oleic acid 22 4,9 658 P-29 no 50 Undecylenic acid 74 5,2 659 P-30 Yes 100 Undecylenic acid 14 1,0 660 P-31 Yes 210 Undecylenic acid 12 0,9 661 P-32 no 235 Undecylenic acid 20 5,0 Example 662: Preparation of pigment preparation Q-1 (not according to the invention)

[0137] An aqueous suspension of Pigment Q as obtained in step b) of Example 17 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation Q-1) Examples 663 to 694: Preparation of pigment preparations Q-2 to O-32 (not according to the invention and according to the invention)

[0138] Analogous to Example 662, in the examples 663 to 694Inventive and non-inventive pigment preparations Q-2 to Q-32 were prepared. In each case, an aqueous suspension of pigment Q as obtained after step b) of Example 17 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 18. Determination of dispersion hardness and heat resistance

[0139] For pigment preparations Q-1 to Q-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 18. Table 18: Pigment preparations with Pigment Q Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 662 Q-1 no 50 Pristerene 4910 74 5,1 663 Q-2 Yes 100 Pristerene 4910 15 1,0 664 Q-3 Yes 210 Pristerene 4910 13 0,9 665 Q-4 no 235 Pristerene 4910 24 4,8 666 Q-5 no 70 Caprylic acid 73 5,0 667 Q-6 no 210 Caprylic acid 72 5,1 668 Q-7 no 70 Nervonic acid 72 5,3 669 Q-8 no 210 Nervonic acid 70 5,4 670 Q-9 no 50 Myristic acid 71 5,3 671 Q-10 Yes 100 Myristic acid 15 0,8 672 Q-11 Yes 150 Myristic acid 13 0,9 673 Q-12 no 235 Myristic acid 21 4,9 674 Q-13 no 50 Palmitic acid 69 5,2 675 Q-14 Yes 150 Palmitic acid 14 0,9 676 Q-15 Yes 210 Palmitic acid 12 0,8 678 Q-16 no 235 Palmitic acid 19 4,9 679 Q-17 no 50 Stearic acid 68 5,1 680 Q-18 Yes 100 Stearic acid 14 0,9 681 Q-19 Yes 210 Stearic acid 12 1,0 682 Q-20 no 235 Stearic acid 21 5,1 683 Q-21 no 50 Behenic acid 78 5,1 684 Q-22 Yes 150 Behenic acid 14 1,0 685 Q-23 Yes 210 Behenic acid 13 0,9 686 Q-24 no 235 Behenic acid 26 4,9 687 Q-25 no 50 oleic acid 75 5,1 688 Q-26 Yes 100 oleic acid 14 1,0 689 Q-27 Yes 210 oleic acid 13 0,9 690 Q-28 no 235 oleic acid 20 4,8 691 Q-29 no 50 Undecylenic acid 76 5,2 692 Q-30 Yes 70 Undecylenic acid 14 1,0 693 Q-31 Yes 210 Undecylenic acid 12 0,9 694 Q-32 no 235 Undecylenic acid 26 5,1 Example 695: Preparation of pigment preparation R-1 (not according to the invention)

[0140] An aqueous suspension of pigment R as obtained in step b) of Example 18 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation R-1) Examples 696 to 726: Preparation of pigment preparations R-2 to R-32 (not according to the invention and according to the invention)

[0141] Analogous to Example 695, in the examples 696 to 726Inventive and non-inventive pigment preparations R-2 to R-32 were prepared. In each case, an aqueous suspension of the pigment R as obtained after step b) of Example 18 was mixed with different aliphatic carboxylic acids B) or mixtures thereof in different amounts, as shown in Table 19. Determination of dispersion hardness and heat resistance

[0142] For pigment preparations R-1 to R-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 19. Table 19: Pigment preparations with Pigment R Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 695 R-1 no 50 Pristerene 4910 74 5,1 696 R-2 Yes 100 Pristerene 4910 15 1,0 697 R-3 Yes 210 Pristerene 4910 14 0,9 698 R-4 no 235 Pristerene 4910 23 4,8 699 R-5 no 70 Caprylic acid 74 5,0 700 R-6 no 210 Caprylic acid 69 5,1 701 R-7 no 70 Nervonic acid 72 5,3 702 R-8 no 210 Nervonic acid 71 5,0 703 R-9 no 50 Myristic acid 72 5,1 704 R-10 Yes 100 Myristic acid 15 1,0 705 R-11 Yes 150 Myristic acid 14 1,1 706 R-12 no 235 Myristic acid 30 5,0 707 R-13 no 50 Palmitic acid 72 5,2 708 R-14 Yes 150 Palmitic acid 14 1,0 709 R-15 Yes 210 Palmitic acid 12 0,9 710 R-16 no 235 Palmitic acid 25 4,9 711 R-17 no 50 Stearic acid 70 5,1 712 R-18 Yes 100 Stearic acid 13 1,0 713 R-19 Yes 210 Stearic acid 12 0,9 714 R-20 no 235 Stearic acid 21 4,9 715 R-21 no 50 Behenic acid 73 5,1 716 R-22 Yes 150 Behenic acid 14 1,0 717 R-23 Yes 210 Behenic acid 13 0,9 718 R-24 no 235 Behenic acid 29 4,9 719 R-25 no 50 oleic acid 73 5,1 720 R-26 Yes 70 oleic acid 14 1,1 721 R-27 Yes 210 oleic acid 13 1,1 722 R-28 no 235 oleic acid 28 4,8 723 R-29 no 50 Undecylenic acid 74 5,2 724 R-30 Yes 100 Undecylenic acid 14 1,0 725 R-31 Yes 210 Undecylenic acid 13 1,0 726 R-32 no 235 Undecylenic acid 21 5,1 Example 727: Preparation of pigment preparation S-1 (not according to the invention)

[0143] An aqueous suspension of Pigment S as obtained in step b) of Example 19 was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation S-1) Examples 728 to 760: Preparation of pigment preparations S-2 to S-32 (not according to the invention and according to the invention)

[0144] Analogous to Example 727, in the examples 728 to 760Inventive and non-inventive pigment preparations S-2 to S-32 were prepared. In each case, an aqueous suspension of pigment S as obtained after step b) of Example 19 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 20. Determination of dispersion hardness and heat resistance

[0145] For pigment preparations S-1 to S-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 20. Table 20: Pigment preparations with Pigment S Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 727 S-1 no 50 Pristerene 4910 74 5,1 728 S-2 no 100 Pristerene 4910 75 5,0 729 S-3 no 210 Pristerene 4910 74 4,9 730 S-4 no 235 Pristerene 4910 76 4,6 731 S-5 no 70 Caprylic acid 74 5,1 734 S-6 no 210 Caprylic acid 71 5,2 735 S-7 no 70 Nervonic acid 73 5,2 736 S-8 no 210 Nervonic acid 72 5,3 737 S-9 no 50 Myristic acid 74 5,2 738 S-10 no 100 Myristic acid 70 5,1 739 S-11 no 150 Myristic acid 72 5,1 740 S-12 no 235 Myristic acid 74 4,8 741 S-13 no 50 Palmitic acid 73 5,1 742 S-14 no 150 Palmitic acid 74 5,0 743 S-15 no 210 Palmitic acid 73 5,1 744 S-16 no 235 Palmitic acid 70 4,8 745 S-17 no 50 Stearic acid 70 5,0 746 S-18 no 100 Stearic acid 69 5,1 747 S-19 no 210 Stearic acid 68 5,2 748 S-20 no 235 Stearic acid 66 4,9 749 S-21 no 50 Behenic acid 73 5,1 750 S-22 no 150 Behenic acid 72 5,0 751 S-23 no 210 Behenic acid 70 4,9 752 S-24 no 235 Behenic acid 72 4,8 753 S-25 no 50 oleic acid 74 5,1 754 S-26 no 70 oleic acid 70 5,0 755 S-27 no 210 oleic acid 69 5,1 756 S-28 no 235 oleic acid 70 4,9 757 S-29 no 50 Undecylenic acid 72 5,2 758 S-30 no 100 Undecylenic acid 70 5,2 759 S-31 no 210 Undecylenic acid 70 5,1 760 S-32 no 235 Undecylenic acid 72 5,0 Example 761: Preparation of pigment preparation T-1 (not according to the invention)

[0146] An aqueous suspension of Pigment T, as obtained in step b) of Example 20, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation T-1) Examples 762 to 792: Preparation of pigment preparations T-2 to T-32 (not according to the invention and according to the invention)

[0147] Analogous to Example 761, in the examples 762 to 792Inventive and non-inventive pigment preparations T-2 to T-32 were prepared. In each case, an aqueous suspension of pigment T as obtained after step b) of Example 20 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 21. Determination of dispersion hardness and heat resistance

[0148] For pigment preparations T-1 to T-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 21. Table 21: Pigment preparations with Pigment T Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 761 T-1 no 50 Pristerene 4910 92 5,1 762 T-2 Yes 100 Pristerene 4910 3 0,1 763 T-3 Yes 210 Pristerene 4910 3 0,1 764 T-4 no 235 Pristerene 4910 8 4,9 765 T-5 no 70 Caprylic acid 90 5,1 766 T-6 no 210 Caprylic acid 89 5,0 767 T-7 no 70 Nervonic acid 92 5,0 768 T-8 no 210 Nervonic acid 91 5,0 769 T-9 no 50 Myristic acid 88 5,1 770 T-10 Yes 100 Myristic acid 4 0,1 771 T-11 Yes 150 Myristic acid 4 0,1 772 T-12 no 235 Myristic acid 15 4,9 773 T-13 no 50 Palmitic acid 90 5,0 774 T-14 Yes 150 Palmitic acid 2 0,1 775 T-15 Yes 210 Palmitic acid 2 0,2 776 T-16 no 235 Palmitic acid 9 4,9 777 T-17 no 50 Stearic acid 86 5,4 778 T-18 Yes 100 Stearic acid 2 0,1 779 T-19 Yes 210 Stearic acid 2 0,1 780 T-20 no 235 Stearic acid 8 4,8 781 T-21 no 50 Behenic acid 93 5,0 782 T-22 Yes 150 Behenic acid 3 0,1 783 T-23 Yes 210 Behenic acid 3 0,2 784 T-24 no 235 Behenic acid 9 4,9 785 T-25 no 50 oleic acid 82 5,1 786 T-26 Yes 70 oleic acid 3 0,2 787 T-27 Yes 210 oleic acid 4 0,2 788 T-28 no 235 oleic acid 10 4,8 789 T-29 no 50 Undecylenic acid 84 5,2 790 T-30 Yes 100 Undecylenic acid 3 0,2 791 T-31 Yes 210 Undecylenic acid 3 0,3 792 T-32 no 235 Undecylenic acid 11 5,1 Example 793: Preparation of pigment preparation U-1 (not according to the invention)

[0149] An aqueous suspension of Pigment U, as obtained in step b) of Example 21, was mixed with 50 g of Pristerene 4910 and stirred for 60 minutes. A pH of 5 was then adjusted with aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80°C in a vacuum drying cabinet, and ground in a standard laboratory mill for approximately 2 minutes. (= Pigment Preparation U-1) Examples 794 to 823: Preparation of pigment preparations U-2 to U-32 (not according to the invention and according to the invention)

[0150] Analogous to Example 793, in the examples 794 to 823Inventive and non-inventive pigment preparations U-2 to U-32 were prepared. In each case, an aqueous suspension of pigment U as obtained after step b) of Example 21 was admixed with various aliphatic carboxylic acids B) or mixtures thereof in various amounts, as indicated in Table 22. Determination of dispersion hardness and heat resistance

[0151] For pigment preparations U-1 to U-32, the dispersion hardness and heat resistance were determined according to Procedures 1 and 2 below. The values ​​can also be found in Table 22. Table 22: Pigment preparations with Pigment U Example Pigment preparation According to the invention Grams of aliphatic carboxylic acid B) or mixture per mole of pigment Aliphatic carboxylic acid B) or mixture Dispersing hardness Heat resistance at 300°C (DE) 793 U-1 no 50 Pristerene 4910 45 5,1 794 U-2 Yes 100 Pristerene 4910 8 0,4 795 U-3 Yes 210 Pristerene 4910 7 0,4 796 U-4 no 235 Pristerene 4910 11 4,7 797 U-5 no 70 Caprylic acid 50 5,1 798 U-6 no 210 Caprylic acid 48 5,1 799 U-7 no 70 Nervonic acid 52 5,1 800 U-8 no 210 Nervonic acid 50 5,5 801 U-9 no 50 Myristic acid 46 5,0 802 U-10 Yes 100 Myristic acid 9 0,6 803 U-11 Yes 150 Myristic acid 9 0,6 804 U-12 no 235 Myristic acid 12 4,9 805 U-13 no 50 Palmitic acid 48 5,0 806 U-14 Yes 150 Palmitic acid 6 0,4 807 U-15 Yes 210 Palmitic acid 6 0,4 808 U-16 no 235 Palmitic acid 12 4,9 809 U-17 no 50 Stearic acid 53 5,1 809 U-18 Yes 100 Stearic acid 7 0,4 810 U-19 Yes 210 Stearic acid 7 0,4 811 U-20 no 235 Stearic acid 15 4,8 812 U-21 no 50 Behenic acid 51 5,1 813 U-22 Yes 150 Behenic acid 9 0,5 814 U-23 Yes 210 Behenic acid 9 0,5 815 U-24 no 235 Behenic acid 13 4,9 816 U-25 no 50 oleic acid 49 5,1 817 U-26 Yes 70 oleic acid 9 0,6 818 U-27 Yes 210 oleic acid 9 0,6 819 U-28 no 235 oleic acid 13 4,9 820 U-29 no 50 Undecylenic acid 50 5,2 821 U-30 Yes 100 Undecylenic acid 8 0,5 822 U-31 Yes 210 Undecylenic acid 8 0,5 823 U-32 no 235 Undecylenic acid 12 5,1 Chemical lists

[0152] fatty acid mixture Typical composition in wt.% Commercial product (company UNIQEMA) C 14 C 16 C 18 Melting range °C Pristerene ®< 4910 2 30 64 57,5-60 Pristerene ®< 4911 2 45 52 55-56 Pristerene ®< 9429 52-60 Pristerene ®< 4922 0,7 30 66 51-55 fatty acid CAS No. Chain length Cn = supplier Caprylic acid (octanoic acid, C 8 H 16 O 2 ) 124-07-2 8 Sigma-Aldrich Capric acid (n-decanoic acid, C 10 H 20 O 2 ) 334-48-5 10 Sigma-Aldrich Lauric acid (dodecanoic acid, C 12 H 24 O 2 ) 143-07-7 12 Sigma-Aldrich Myristic acid (tetradecanoic acid, C 14 H 28 O 2 ), 544-63-8 14 Sigma-Aldrich Palmitic acid (hexadecanoic acid, C 16 H 32 O 2 ), 57-10-3 16 Sigma-Aldrich Stearic acid (octadecanoic acid, C 18 H 36 O 2 ) 57-11-4 18 Sigma-Aldrich Behenic acid (n-docosanic acid, C 22 H 44 O 2 ) 112-85-6 22 Sigma-Aldrich Lignoceric acid (tetracontanoic acid, C 24 H 43 O 2 ) 557-59-5 24 Sigma-Aldrich Oleic acid ((9Z)-octadec-9-enoic acid, C 18 H 34 O 2 ) 112-80-1 18 Alfa Undecylenic acid (undec-10-enoic acid, C 11 H 20 O 2 ) 112-38-9 11 Alfa Nervous acids (( Z )-15-Tetracosensic acid, C 24 H 46 O 2 ) 506-37-6 24 Sigma-Aldrich

[0153] The pigments prepared according to Examples 1 to 22 and the pigment preparations prepared according to Examples 23 to 23 were each subjected to a determination of the dispersion hardness according to Procedure 1 and the heat stability according to Procedure 2. Regulation 1: Determination of dispersion hardness

[0154] The dispersion hardness was measured in accordance with DIN 53 775, Part 7, with the cold rolling temperature being 25°C and the hot rolling temperature being 150°C. All dispersion hardnesses stated in this application were determined according to this modified DIN standard.

[0155] Samples with dispersion hardnesses of less than 20 are rated as good. Regulation 2: Determination of heat stability

[0156] The heat stability is determined according to DIN EN 12877-2

[0157] For this purpose, samples of the pigment preparations were mixed with the test medium polyamide 6 (type Durethan B30S with 1% titanium dioxide).

[0158] The samples thus produced were processed according to procedure A of the standard by injection molding at 240°C and 2.5 minutes residence time in the screw and at 300°C and 5 minutes residence time in the screw.

[0159] The color difference (dE) between the samples produced at the low test temperature and the samples produced at the higher test temperatures was determined by colorimetric evaluation according to ISO 7724-2: 1984, 4.1.1, and ISO 7724-3.

[0160] Samples with dE values ​​less than or equal to 2 are considered heat stable. Conclusion

[0161] The measured values ​​in Tables 1 to 22 show that only the pigment preparations according to the invention exhibit both low dispersion hardness (< 20 ) and good heat stability (dE < 2). This means that the non-inventive pigment preparations are less dispersible (ie, less processable in plastics) and, moreover, have significantly poorer heat stability properties than the pigment preparations according to the invention.

Claims

1. Pigment preparations, characterized in that they at least contain i) a metal azo pigment A) containing the components a) at least two metal azo compounds of the formula (I) which differ at least in the metal ion Me, or the tautomeric forms thereof, in which R1 and R2 are each independently OH, NH2 or NHR5, R3 and R4 are each independently =O or =NR5, R5 is hydrogen or alkyl, preferably C1-C4-alkyl, and Me is a metal ion Me1 or Me2, wherein Me1 is Cu2+ or Ni2+ and Me2 is Zn2+, Al3+2 / 3, Fe2+, Fe3+2 / 3, Co2+, Co3+2 / 3, La3+2 / 3, Ce3+2 / 3, Pr3+2 / 3, Nd2+, Nd3+2 / 3, Sm2+, Sm3+2 / 3, Eu2+, Eu3+2 / 3, Gd3+2 / 3, Tb3+2 / 3, Dy3+2 / 3, Ho3+2 / 3, Yb2+, Yb3+2 / 3, Er3+2 / 3, Tm3+2 / 3, Mg2+, Ca2+, Sr2+, Mn2+, Y3+2 / 3, Sc3+2 / 3, Ti2+, Ti3+2 / 3, Nb3+2 / 3, Mo2+, Mo3+2 / 3, V2+, V3+2 / 3, Zr2+, Zr3+2 / 3, Cd2+, Cr3+2 / 3, Pb2+ or Ba2+, with the proviso that the amount of metal ions Me1 in total is 97 to 100 mol% and the amount of metal ions selected from the series Me2 in total is 0 to 3 mol%, based in each case on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum total of the compounds of the formula (I) is 99.9:0.1 to 0.1:99.9, and b) at least one compound of the formula (II) in which R6 is hydrogen or alkyl, preferably C1-C4-alkyl optionally mono- or polysubstituted by OH, and ii) at least one aliphatic monocarboxylic acid B) having 10 to 22 carbon atoms in an amount of from 70 to 210 g based on 1 mol of all metal azo compounds (I) present in the metal azo pigment A).

2. Pigment preparations according to Claim 1, characterized in that the metal azo pigments A) contain adducts of components a) and b) as specified in Claim 1.

3. Pigment preparations according to Claim 1 or 2, characterized in that the metal azo pigments A) contain adducts of the components a) at least two metal azo compounds of the formula (I) as specified in Claim 1, in which R1 and R2 are OH, R3 and R4 are =O, Me1 is Cu2+ or Ni2+ and Me2 is Zn2+, Al3+2 / 3, Fe2+, Fe3+2 / 3, Co2+, Co3+2 / 3, La3+2 / 3, Ce3+2 / 3, Pr3+2 / 3, Nd2+, Nd3+2 / 3, Sm2+, Sm3+2 / 3, Eu2+, Eu3+2 / 3, Gd3+2 / 3, Tb3+2 / 3, Dy3+2 / 3, with the proviso that the amount of metal ions Me1 in total is 99 to 100 mol% and the amount of metal ions Me2 in total is 0 to 1 mol%, based in each case on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum total of the compounds of the formula (I) is 0.5:99.5 to 10:90, and b) at least one compound of the formula (II) as specified in Claim 1, in which R6 is hydrogen.

4. Pigment preparations according to at least one of Claims 1 to 3, characterized in that the metal azo pigments A) contain adducts of the components a) at least two metal azo compounds of the formula (I) as specified in Claim, in which R1 and R2 are OH, R3 and R4 are =O, Me1 is Cu2+ or Ni2+ and Me2 is Zn2+, Al3+2 / 3, Fe2+, Fe3+2 / 3, Co2+, Co3+2 / 3, with the proviso that the amount of metal ions Me1 in total is 99 to 100 mol% and the amount of metal ions Me2 in total is 0 to 1 mol%, based in each case on one mole of all compounds of the formula (I), and wherein the molar ratio of Cu to Ni metal ions in the sum total of the compounds of the formula (I) is 1:99 to 5:95, and b) at least one compound of the formula (II) as specified in Claim 1, in which R6 is hydrogen.

5. Pigment preparations according to at least one of Claims 1 to 4, characterized in that the metal azo pigments A) contain adducts of the components a) at least two metal azo compounds of the formula (I) as specified in Claim 1, in which R1 and R2 are OH, R3 and R4 are =O and Me is a metal ion Me1, with the proviso that the amount of metal ions Me1 in total is 100 mol%, based on one mole of all compounds of the formula (I), and the molar ratio of Cu to Ni metal ions in the sum total of the compounds of the formula (I) is 1:99 to 5:95, and b) at least one compound of the formula (II) as specified in Claim 1, in which R6 is hydrogen.

6. Pigment preparations according to at least one of Claims 1 to 5, characterized in that the metal azo pigments A) have a BET specific surface area (m2 / g) of 50 to 200 m2 / g, preferably of 80 to 160 m2 / g and very particularly preferably of 100 to 150 m2 / g, determined in accordance with DIN 66131.

7. Pigment preparations according to at least one of Claims 1 to 6, characterized in that the aliphatic monocarboxylic acids B) are saturated or mono- or polyunsaturated.

8. Pigment preparations according to at least one of Claims 1 to 7, characterized in that the aliphatic monocarboxylic acids B) contain 10 to 22 carbon atoms and are saturated or mono- to triunsaturated.

9. Pigment preparations according to at least one of Claims 1 to 8, characterized in that the aliphatic monocarboxylic acids B) contain 12 to 22 carbon atoms and are saturated or mono- or diunsaturated.

10. Pigment preparations according to at least one of Claims 1 to 9, characterized in that the aliphatic monocarboxylic acids B) contain 14 to 18 carbon atoms and are saturated or monounsaturated.

11. Pigment preparations according to at least one of Claims 1 to 10, characterized in that they contain tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid) and / or octadecanoic acid (stearic acid).

12. Pigment preparations according to at least one of Claims 1 to 11, characterized in that they contain a mixture of 0.5% to 5% by weight, preferably 1% to 3% by weight, of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 14 carbon atoms, 25% to 60% by weight, preferably 30% to 50% by weight, of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 16 carbon atoms and 40% to 75% by weight, preferably 45% to 65% by weight, of at least one saturated or monounsaturated aliphatic monocarboxylic acid having 18 carbon atoms.

13. Pigment preparations according to at least one of Claims 1 to 12, characterized in that they contain 100 to 180 g, particularly preferably 120 to 160 g, of at least one aliphatic monocarboxylic acid B), based in each case on one mole of all metal azo compounds (I) present in the metal azo pigment A).

14. Process for producing a pigment preparation according to at least one of Claims 1 to 13, characterized in that at least one metal azo pigment A) is mixed with at least one aliphatic monocarboxylic acid B) and optionally one or more auxiliaries and / or additives.

15. Use of a pigment preparation according to at least one of Claims 1 to 13 for the bulk colouring of synthetic, semisynthetic or natural macromolecular substances, especially polyvinyl chloride, polystyrene, polyamide, polyethylene or polypropylene, and for the spin dyeing of natural, regenerated or synthetic fibres, such as for example cellulose, polyester, polycarbonate, polyacrylonitrile or polyamide fibres, and for the printing of textiles and paper.