Pigment preparations

Abstract

To provide pigment preparations.SOLUTION: The present invention relates to new pigment preparations based on metal azo pigments and aliphatic C10-22 monocarboxylic acids, to processes for their production and their use as a yellow pigment for coloring plastic products, and to the use of aliphatic C10-22 monocarboxylic acids for improved filtration properties of pigment preparations with simultaneously improved coloring power.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a metal azo pigment and an aliphatic C 10~22 Novel pigment preparations based on monocarboxylic acids, their production process and their use as yellow pigments for coloring plastic products, as well as the use of aliphatic C pigments for improving the tinctorial strength and at the same time improving the filtration properties of the pigment preparation 10~22 The use of monocarboxylic acids. [Background technology]

[0002] Metal complexes of azobarbituric acid and nickel salts and their use as yellow pigments have been extensively described in the literature, for example in . It is also known that these products can be further reacted, for example with melamine or melamine derivatives, in order to improve the performance properties of the pigments, in particular in the coloring of plastics and paints, as well as as color filters for LCDs (liquid crystal displays). It is also mentioned in the literature that, in addition to the nickel salt, these metal azo complexes can contain at least one further salt of various metals in order to tailor the coloring properties. . . . . . . . discloses metal complexes of azo compounds based on alkali metals, alkaline earth metals, lanthanides, aluminum, scandium, titanium, vanadium, chromium, manganese, cobalt, copper, nickel and zinc. The pigments according to . . . have a different color locus compared to the pure nickel-azobarbituric acid complexes. The color locus refers to the position of a measured or selected color in a color space, and is usually defined by coordinates, preferably using the coordinates L*, a* and b* in the CIELAB color space. The amount of all color positions in a color space is called a gamut or color gamut; see (Non-Patent Document 2). (Patent Document 1) describes the binder tinting strength measured according to (Non-Patent Document 3), but does not describe the filterability or the determination of the filter pressure value FPV according to DIN EN ISO 23900-5:2019-01.

[0003] Furthermore, the literature also discloses treatments of the pigment surface with adjuvants. For example, the dispersibility of the pigments will be improved by such surface coatings. However, an increase in the coating of the pigment surface is always accompanied by a loss of tinting strength. Such surface treatments of azo pigments are known, for example, from (Non-Patent Document 4).

[0004] From (Patent Document 2) and (Patent Document 3), pigments based on metal-azobarbituric acid and melamine are known, which contain copper and nickel ions and optionally further metal ions. These pigments are of interest due to their improved color strength and at the same time improved dispersion properties. However, (Patent Document 2) and (Patent Document 3) are silent on the determination of filterability or the filter pressure value FPV according to DIN EN ISO 23900-5:2019-01.

[0005] From US Pat. No. 4,993,239 pigments based on metal-azobarbituric acid and melamine are known, which contain copper and nickel ions, optionally further metal ions, and have a surface coating with specific fatty acid derivatives. These products are characterized by improved heat stability and supposedly high color strength, although more precise information about the latter is not available.

[0006] Patent document 5 discloses, among others, five nickel azobarbiturate melamine pigments with improved dispersibility. Patent document 5 does not describe the relative tinting strength, or the filterability, or the determination of the filter pressure value FPV according to DIN EN ISO 23900-5:2019-01. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] European Patent Application Publication No. A 1 591 489 [Patent Document 2] European Patent Application Publication No. A 3 072 932 [Patent Document 3] European Patent Application Publication No. A 3 222 680 [Patent Document 4] European Patent Application Publication No. 3 981 840 [Patent Document 5] European Patent Application Publication No. A 1 612 246 [Non-patent literature]

[0008] [Non-Patent Document 1] W. Herbst, K. Hunger, Industrial Organic Pigments, 3rd edition 2004, pp.390-397 [Non-Patent Document 2] https: / / de.wikipedia.org / wiki / Farbraum [Non-Patent Document 3] Bayer Farben Revue,Special Issue 3 / 2 D,Farbmessung[Colour measurement]1986 [Non-Patent Document 4] W. Herbst, K. Hunger, Industrial Organic Pigments (Production, Properties, Applications), 3rd Completely Revised Edition (2004), Wiley-VCH-Verlag, pp.202-203 Summary of the Invention [Problem to be solved by the invention]

[0009] The metal azo pigments known from the prior art are inadequate in terms of their performance properties and therefore there is a need for improved metal azo pigments, in particular with regard to at least filtration properties with retention of tinting strength.

[0010] Now, surprisingly, at least one aliphatic C 10~22The pigment preparation based on at least two zinc- and nickel-based metal azo compounds in combination with monocarboxylic acids is preferably prepared by mixing 100 to 250 g of aliphatic C per mole of all metal azo compounds contained in the metal azo pigment. 10~22 It has been found that the use of monocarboxylic acids provides improved tint strength as well as improved filtration properties. [Means for solving the problem]

[0011] The subject of the present invention is the following: i) Below: a) Formula (I): [ka] (In the formula, R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 is alkyl, Me is a metal ion Me in the first metal azo compound. 1 and a metal ion Me in the second metal azo compound. 2 and Where: Me 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me 2 Al 3+ 2 / 3 , Fe 2+ , Fe 3+ 2 / 3 , Co 2+ , Co 3+ 2 / 3 , La 3+ 2 / 3 , Ce3+ 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+ , 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+ is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) Formula (II) [ka] (In the formula, R 6 is independently in each occurrence hydrogen or alkyl, preferably C 1 ~C 4 alkyl, which may be substituted one or more times by OH or a reaction product of (I) and (II), preferably a reaction product of (I) and melamine, A metallic azo pigment comprising (ii) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) 10~22 Monocarboxylic acid B) It is a pigment preparation consisting of

[0012] However, the present invention provides the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 is alkyl, Me is a metal ion Me in the first metal azo compound. 1 and a metal ion Me in the second metal azo compound. 2 and Where: Me 1 Zn 2+ and Ni 2+and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me 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+ , 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 , Pb2+ Or Ba 2+ is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) Formula (II) [ka] (In the formula, R 6 is independently in each occurrence hydrogen or alkyl, preferably C 1 ~C 4 alkyl, which may be substituted one or more times by OH or a reaction product of (I) and (II), preferably a reaction product of (I) and melamine, at least one aliphatic C 10~22 The use of monocarboxylic acids B) In this case, 100 to 250 g of aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment (A) is 10~22 Monocarboxylic acids B) are used.

[0013] The present invention also relates to a method for producing a pharmaceutical composition comprising the steps of: a) Formula (I): [ka] (In the formula, R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 is alkyl, Me in the first metal azo compound is Me 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me in the second metal azo compound is Me 2 It is called 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 , Sc 3+ 2 / 3 , Ti2+ , 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+ is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) Formula (II) [ka] (In the formula, R 6 is independently in each occurrence hydrogen or alkyl, preferably C 1 ~C 4 alkyl, which may be substituted one or more times by OH or a reaction product of (I) and (II), preferably a reaction product of (I) and melamine, 1. A process for simultaneously improving the filter pressure value FPV, determined by pressure filter test according to DIN EN ISO 23900-5:2019-01, and the tinting strength, determined according to DIN 55986, of a pigment preparation containing a metal azo pigment A) consisting of 100 to 250 g of at least one aliphatic C per mole of all metal azo compounds (I) contained in the metal azo pigment A) 10~22 It also relates to a process by using monocarboxylic acids B).

[0014] In formula (I), when Me is a trivalent metal ion, the charge is determined by the formula (Ia): [ka] (R 1 , R 2 , R 3 and R 4 has the meaning given for formula (I). equivalents in each case by anionic structural units of 1.

[0015] For clarity, it should be noted that the scope of the present invention encompasses all definitions and parameters recited in any desired combination, either in the general or preferred ranges. This also applies to the amounts used in the processes and uses claimed under this application. Standards cited in connection with this application relate to the editions current as of the filing date of the present invention. Percentages reported are weight percents, unless otherwise stated. Substituents in the sense of alkyl are linear or branched hydrocarbon radicals, preferably C 1 ~C 6 Alkyl, particularly preferably C 1 ~C 4 refers to alkyl, which may be substituted with identical or different substituents, in particular chlorine, bromine, fluorine; -OH, -CN, -NH 2 Or C 1 ~C 6 It may be substituted one or more times by alkoxy.

[0016] Tinting strength is a colorimetric quantity that describes the tinting ability of a colorant. A distinction is made between absolute and relative tinting strength. Tinting strength is the most important property of a pigment, see: https: / / de.wikipedia.org / wiki / Farbstaerke.

[0017] In the context of the present invention, the relative tinting strength is determined according to DIN 55986. In the production of pigments, it is common to use the relative tinting strength rather than the absolute tinting strength measured against a standard. For this purpose, each batch to be tested is dispersed and used for tinting under the same conditions as the standard. The quotient (sample / standard) of the K / S value (Kubelka-Munk) represents an index of the light absorption of the entire system and is called the relative tinting strength and is expressed as a percentage:

number

[0018] A value of 100% means that the sample has the same tinting strength as the standard; higher values ​​mean higher tinting strength and therefore less amount of pigment needed to induce a given hue.

[0019] The filter pressure value FPV is determined within the scope of the present invention by a pressure filter test according to DIN EN ISO 23900-5:2019-01 (Determination of pressure rise / Protocol 2). This standard specifies a method for measuring the degree of dispersion of colorants in thermoplastics. This process is suitable for testing colorants in the form of color concentrates in any plastics used in extrusion and melt spinning processes. The filter pressure values ​​determined by this method are only valid for the equipment, conditions and plastics tested used. The use of test conditions other than those specified may lead to different results. This part of ISO 23900 does not provide any description of the production of color concentrates. The test results of individual colorants are therefore only comparable if the same method is used to produce the color concentrates. In accordance with DIN EN ISO 23900-5:2019-01, each pigment preparation to be examined is intensively mixed in a tumble mixer in polyamide 6 in the form of Durethan® B30S from LANXESS Deutschland GmbH, Cologne, with the addition of 1% titanium dioxide. The mixture thus obtained is extruded in a Leistritz ZSE 18HP twin-screw extruder at 225° C. and 700 rpm, the granulate thus produced is filtered through a 25 μm filter at a temperature of 238° C. and the resulting pressure rise is measured. The pressure difference between the initial pressure and the maximum pressure is used to calculate the filter pressure value FPV. The lower this pressure rise, measured in bar / g, the better the filterability of the pigment preparation considered in connection with the present invention.

[0020] Preferably, component a) contained in the metal azo pigments used in the present invention forms a so-called adduct together with component b), where adduct according to the present invention means a "complex molecule". The bond between the molecules of such an adduct preferably occurs by intermolecular interactions, Lewis acid-base interactions or coordinate bonds. According to the present invention, the term "adduct" generally includes all types of intercalation or addition compounds.

[0021] The term "intercalation compound" or "addition compound" within the meaning of the present invention is understood to refer in particular to compounds formed by intermolecular interactions such as van der Waals interactions or Lewis acid-base interactions. How the intercalation proceeds depends both on the chemical nature of the component to be intercalated and on the chemical nature of the host lattice. Such compounds are often also called intercalation compounds. In a chemical sense, this refers to the incorporation of molecules, ions (and sometimes even atoms) into a compound.

[0022] Furthermore, the term "adduct" also includes inclusion compounds, so-called clathrates, which refer to compounds of two substances in which one guest molecule is incorporated into a lattice or cage composed of a host molecule.

[0023] The term "intercalation compound" or "addition compound" within the scope of the present definition also includes mixed intercalation crystals or interstitial compounds, which are chemically non-stoichiometric, crystalline compounds of at least two elements.

[0024] Furthermore, the terms "intercalation compounds" or "addition compounds" in the context of the present invention are understood to mean compounds formed on the basis of coordinate or complex bonds. Such compounds are in particular called mixed substitution or replacement crystals, in which at least two substances form a common crystal, the atoms of the second component being located in the regular lattice sites of the first component.

[0025] Compounds suitable for forming the above-defined adducts with the metal azo compounds of formula (I) can be both organic and inorganic compounds, hereinafter referred to as adduct formers.

[0026] Suitable adduct formers are in principle derived from the most diverse classes of compounds. For purely practical reasons, preference is given to compounds which are liquid or solid under standard conditions (25°C, 1 bar). Among the liquid substances, preference is given to those which generally have a boiling point above 100°C, preferably above 150°C at 1 bar. Suitable adduct formers are generally acyclic and cyclic organic compounds, preferably aliphatic or aromatic hydrocarbons, which in particular contain OH, COOH, NH 2 , substituted NH 2 ,CONH 2 , replace CONH 2 , S.O. 2 NH 2 , substitution SO 2 NH 2 , S.O. 3 H, halogen, NO 2 , CN, -SO 2 -Alkyl, -SO 2 It may be substituted by -aryl, -O-alkyl, -O-aryl, -O-acyl.

[0027] Carboxamides and sulfonamides are a preferred group of adduct formers.In particular, urea and substituted ureas, such as phenylurea, dodecylurea, and their polycondensates with aldehydes, especially formaldehyde, are also suitable, as well as heterocycles, preferably 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.

[0028] A polymer, preferably a water-soluble polymer, in particular preferably having an M of 1000 or more, in particular 1000 to 10000 g / mol. nLikewise suitable as adduct formers are ethylene-propylene oxide block polymers having the formula (I) below, polyvinyl alcohol, poly(meth)acrylic acid, modified celluloses, preferably carboxymethyl cellulose, hydroxyethyl cellulose and hydroxypropyl cellulose, methylhydroxyethyl cellulose and ethylhydroxyethyl cellulose.

[0029] According to the invention, the adduct former used is of formula (II): Melamine is particularly preferred according to the invention.

[0030] Preferred embodiments of the present invention Preferred subjects of the invention are: i) Below: a) Formula (I): [ka] (In the formula, R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 is alkyl, Me is a metal ion Me in the first metal azo compound. 1 and a metal ion Me in the second metal azo compound. 2 and Where: Me 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me 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+ , 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+ is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me 1The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) Formula (II) [ka] (In the formula, R 6 is independently in each occurrence hydrogen or alkyl, preferably C 1 ~C 4 alkyl, which may be substituted one or more times by OH and at least one compound of Metallic azo pigment A) and (ii) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) 10~22 Monocarboxylic acid B) It is a pigment preparation consisting of

[0031] Preferably, in the metal azo pigment A), the ratio of the metal azo compound (I) to the compound of formula (II) is 1 mol:0.05-4 mol, more preferably 1 mol:0.5-2.5 mol, particularly preferably 1 mol:1.0-2.0 mol.

[0032] In one embodiment, the metal azo compounds A) contained in the pigment preparation according to the invention are a physical mixture of a) at least two metal azo compounds of formula (I) and b) at least one adduct of a compound of formula (II).Preferably, they are physical mixtures of adducts of pure Ni-azo compounds with melamine and adducts of pure Zn-azo compounds with melamine.

[0033] However, particularly preferably, the metal azo pigments A) contained in the pigment preparation according to the invention are chemical mixtures of a) at least two metal azo compounds of the formula (I) and b) at least one adduct of a compound of the formula (II). These chemical mixtures contain Ni and Zn atoms and, optionally, further metal ions Me2 are adducts of metal azo compounds incorporated into a common crystal lattice.

[0034] Preferred subjects of the invention are: i) Below: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound is Me 1 Zn 2+ and Ni 2+ where the molar ratio of metal ions Zn:Ni is 97:3 to 3:97, and Me in the second metal azo compound is Me 2 Me 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 , Tm3+ 2 / 3 , Mg 2+ , Ca 2+ , Sr 2+ , Mn 2+ Or Y 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+ is) at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1), or alternatively the reaction product of formula (I) with melamine, Metallic azo pigment A) and ii) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) 10~22 Monocarboxylic acid B) It is a pigment preparation consisting of

[0035] The present invention particularly preferably comprises the following: i) Below: a) Formula (I): [ka] (In the formula, R 1 and R 2is OH, R 3 and R 4 is O, Me in the first metal azo compound is Me 1 Zn 2+ and Ni 2+ wherein the molar ratio of metal ions Zn:Ni is 90:10 to 30:70; Me in the second metal azo compound is Me 2 This is called Al 3+ 2 / 3 , Fe 2+ , Fe 3+ 2 / 3 , Co 2+ , Co 3+ 2 / 3 , Ce 3+ 2 / 3 , Mg 2+ , Ca 2+ , Sr 2+ , La 3+ 2 / 3 , Mg 2+ , Mn 2+ , Nd 2+ , Nd 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+ , Ca 2+ Or Ba 2+ is) at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1), or alternatively the reaction product of formula (I) with melamine, Metallic azo pigment A) and i) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) 10~22 Monocarboxylic acid B) The present invention relates to a pigment preparation comprising:

[0036] The present invention particularly preferably comprises: i) Below: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound is Me 1 Zn 2+ and Ni 2+ wherein the molar ratio of metal ions Zn:Ni is 40:80 to 20:60; Me in the second metal azo compound is Me 2 This is called Al 3+ 2 / 3 , Fe 2+ , Fe 3+ 2 / 3 , Ca 2+ , Co 2+ , Co 3+ 2 / 3 , La 3+ 2 / 3 , Mg 2+ , Nd 2+ Or Nd 3+ 2 / 3 is) at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of metal ions Me is 97-100 mol%.2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1), or alternatively the reaction product of formula (I) with melamine, Metallic azo pigment A) and ii) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) 10~22 Monocarboxylic acid B) The present invention relates to a pigment preparation comprising:

[0037] Preferably, zinc and nickel are present in the at least two metal azo compounds of the metal azo pigment of the present invention at 3 to 0 mol % of Me 2 The ratio of Zn to Ni is 3-97 mol%.

[0038] Zinc and nickel are particularly preferably present in the at least two metal azo compounds of the metal azo pigment of the present invention in an amount of 3 to 0 mol % Me 2 The ratio of Zn to Ni is 30-90 mol% and 70-10 mol% respectively.

[0039] Particularly preferably, zinc and nickel are contained in at least two kinds of metal azo compounds of the metal azo pigment of the present invention in an amount of 3 to 0 mol % Me 2 The ratio of Zn to Ni is 80-40 mol% and 60-20 mol% respectively.

[0040] More preferably, zinc and nickel are present in the at least two metal azo compounds of the metal azo pigment of the present invention at 0 mol % Me 2 The ratio of Zn to Ni is 80-40 mol% and 60-20 mol% respectively.

[0041] The metal azo pigments A) contained in the pigment preparation according to the invention preferably have a specific surface area BET, determined according to DIN 66131 (Determination of the specific surface area of ​​solids by gas adsorption according to Brunauer, Emmett and Teller (BET)), of between 50 and 200 m 2 / g, particularly preferably 80 to 160m 2 / g, particularly preferably 100 to 150m 2 / g.

[0042] The metal azo pigments A) contained in the pigment preparation according to the invention are known in principle. In this respect, reference can be made to EP-A 3 072 932 or EP-A 3 222 680 and the preparation processes described therein.

[0043] Preferably, the metallic azo pigment A) is one of the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 is alkyl, Me is the metal ion Me 1 Or Me 2 and Here, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me in the second metal azo compound (I)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 , 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+ is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me 1 The total amount of Me is 97-100 mol%, 2 The amount of metal ions selected from the series is 0 to 3 mol% in total. b) Formula (II) [ka] (In the formula, R 6 is hydrogen or alkyl, preferably C 1 ~C 4 alkyl, which may be substituted one or more times with OH can be obtained by reaction with at least one of the compounds of

[0044] The metal azo compound (I) is represented by the formula (III): [ka] (In the formula, X is an alkali metal ion, preferably a sodium or potassium ion; R 1 and R 2 are each independently OH, NH 2 or NHR 5 and R 3 and R 4 each independently represents O or NR 5 and R 5 is hydrogen or alkyl, preferably C 1 ~C 4 (It is alkyl) or a tautomer thereof, preferably the sodium or potassium salt, Nickel and zinc salts, and optionally: Al 3+ 2 / 3 , Fe 2+ , Fe 3+ 2 / 3 , Co 2+ , Co3+ 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 , 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+ One or more Me from the salt series 2 A metal salt; It can be obtained by the reaction wherein, per mole of the compound of formula (III), 0.001 to 0.999 mol of at least one nickel salt, 0.001 to 0.999 mol of at least one zinc salt, and Me 2 0.03-0 mol of at least one metal salt from the series of metal salts is used.

[0045] The synthesis of the metal azo compound (I) in the context of the present invention involves the use of 0.03 to 0.97 mol of at least one nickel salt, 0.97 to 0.03 mol of at least one zinc salt and the Me salt described per mole of the compound of formula (III). 2 It is preferred to use 0.03 to 0 mol of at least one metal salt from the series of metal salts.

[0046] The synthesis of the metal azo compound (I) in the context of the present invention involves the use of 0.1 to 0.7 mol of at least one nickel salt, 0.9 to 0.3 mol of at least one zinc salt and the Me salt described per mole of the compound of formula (III). 2 It is particularly preferable to use 0.03 to 0 mol of at least one metal salt from the series of metal salts.

[0047] The synthesis of the metal azo compound (I) in the context of the present invention involves the use of 0.2 to 0.6 mol of at least one nickel salt, 0.8 to 0.4 mol of at least one zinc salt and the Me salt described per mole of the compound of formula (III). 2 It is particularly preferable to use 0.03 to 0 mol of at least one metal salt from the series of metal salts.

[0048] For the synthesis of the metal azo compound (I), it is more preferable in connection with the present invention to use 0.2 to 0.6 mol of at least one nickel salt and 0.4 to 0.4 mol of at least one zinc salt per mole of the compound of formula (III).

[0049] Preferably, the ratio of the components in the metal azo pigment A) is 1 mol of the compound of formula (I): 0.05-4 mol of the compound of formula (II), more preferably 1 mol of the compound of formula (I): 0.5-2.5 mol of the compound of formula (II), particularly preferably 1 mol of the compound of formula (I): 1.0-2.0 mol of the compound of formula (II).

[0050] The process for producing the metallic azo pigments A) is preferably carried out in an aqueous solution with a pH of less than 7 at a temperature of 60 to 95° C. The nickel and zinc salts used, as well as the optional further Me salts, 2 The metal salts can be used individually or in admixture with one another, preferably in the form of aqueous solutions. The compounds of formula (II) can likewise be added individually or in admixture with one another, preferably in solid form.

[0051] Preferably, the process for producing the metallic azo pigments A) is carried out as follows: the azo compound of formula (III), preferably as a Na or K salt, is first introduced, then one or more of the compounds of formula (II) to be intercalated or added, in particular melamine, are added, either simultaneously or successively, at least one nickel salt and at least one zinc salt, and optionally one or more Me salts. 2 The reaction with metal salts, preferably in the form of aqueous solutions of these salts, is preferably carried out at a pH value of less than 7. Suitable substances for adjusting the pH are sodium hydroxide solution, potassium hydroxide solution, sodium carbonate, sodium hydrogen carbonate, potassium carbonate and potassium hydrogen carbonate.

[0052] Suitable nickel and zinc salts are preferably their water-soluble salts, especially chlorides, bromides, acetates, formates, nitrates, sulfates, etc. Nickel and zinc salts for preferred uses have a water solubility of more than 20 g / l, especially more than 50 g / l at 20° C.

[0053] Suitable Me 2 The metal salt is preferably a water-soluble Me 2 Salts, particularly preferably Me 2Chloride, Me 2 Bromide, Me 2 Acetate, Me 2 Nitrate and Me 2 Sulfates, more particularly preferably Me 2 It is a chloride.

[0054] The metallic azo pigment A) thus obtained can then be isolated as an aqueous filter cake by filtering its aqueous suspension. This filter cake can be washed, preferably with hot water, and then dried by conventional drying methods. Suitable drying methods are, inter alia, paddle drying or spray drying of the corresponding aqueous slurry. Finally, the pigment can be ground again.

[0055] Furthermore, the metallic azo pigment A) contained in the pigment preparation according to the invention has a structure in which Me is Ni 2+ The metal azo compound adduct of formula (I) represented by Me is Zn 2+ and optionally wherein Me is a metal ion Me 2 The metal azo compound of formula (I) may also be prepared by mixing with one or more adducts of the metal azo compound of formula (I)

[0056] Aliphatic C contained in the pigment preparation according to the invention 10~22 The monocarboxylic acids B) may be saturated or mono- or polyunsaturated. Preferably, they are aliphatic C 10~22 The monocarboxylic acids B) are saturated or mono- to tri-unsaturated carboxylic acids. Particularly preferred are aliphatic C) monocarboxylic acids contained in the pigment preparation according to the invention. 10~22 The monocarboxylic acids B) are saturated or mono- or diunsaturated carboxylic acids.

[0057] Particularly preferred are the following: n-decanoic acid (CAS No. 334-48-5, capric acid, C 10 H 20 O 2 ), undec-10-enoic acid (CAS No. 112-38-9, undecylenic acid, C 11 H 20 O 2), dodecanoic acid (CAS No. 143-07-7, lauric acid, C 12 H 24 O 2 ), Tetradecanoic acid (CAS No. 544-63-8, Myristic acid, C 14 H 28 O 2 ), Hexadecanoic acid (CAS No. 57-10-3, Palmitic acid, C 16 H 32 O 2 ), Octadecanoic acid (CAS No. 57-11-4, Stearic acid, C 18 H 36 O 2 ), (9Z)-Octadec-9-enoic acid (CAS No. 112-80-1, Oleic acid, C 18 H 34 O 2 ) and n-docosanoic acid (CAS No. 112-85-6, behenic acid, C 22 H 44 O 2 At least one aliphatic C 10~22 Monocarboxylic acids B) are used.

[0058] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention contain from 14 to 18 carbon atoms and are saturated or monounsaturated.

[0059] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention are tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid) and (9Z)-octadecane-9-enoic acid (oleic acid).

[0060] Aliphatic C contained in the pigment preparation according to the invention 10~22 The monocarboxylic acids B) may be present in pure form or as mixtures.

[0061] Preferably, the mixture of aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention is a mixture comprising at least one saturated or monounsaturated aliphatic monocarboxylic acid having 14 carbon atoms, at least one saturated or monounsaturated aliphatic monocarboxylic acid having 16 carbon atoms, and at least one saturated or monounsaturated aliphatic monocarboxylic acid having 18 carbon atoms.

[0062] Preferably, the mixture of aliphatic monocarboxylic acids B) used according to the invention comprises 0.5 to 5% by weight, particularly 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.

[0063] Particularly preferably, the mixture of aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention is a mixture which contains myristic acid, palmitic acid and stearic acid in the amounts in the preferred ranges indicated above.

[0064] Such mixtures are known as commercial products of the company Unichema under the trade name "Pristerene®", where the different chemical and quantitative composition of these mixtures are characterized by a four-digit number code: Pristerene® 4910, which comprises a mixture of 2% by weight of myristic acid, 30% by weight of palmitic acid and 64% by weight of stearic acid, Pristerene® 4911, which comprises a mixture of 2% by weight of myristic acid, 45% by weight of palmitic acid and 52% by weight of stearic acid, Pristerene® 4922, which comprises a mixture of 0.7% by weight of myristic acid, 30% by weight of palmitic acid and 66% by weight of stearic acid, and Pristerene® 9429.

[0065] The pigment preparation according to the invention preferably comprises from 100 to 250 g of at least one aliphatic monocarboxylic acid B), based on 1 mol of all metal azo compounds (I) contained in the metal azo pigment A).

[0066] Particularly preferably, the pigment preparation according to the invention comprises from 100 to 180 g, particularly preferably from 120 to 160 g, of at least one aliphatic monocarboxylic acid B), in each case based on 1 mol of the total metal azo compounds (I) contained in the metal azo pigment A).

[0067] The pigment preparation of the present invention can be produced by mixing at least one metal azo pigment A) with at least one aliphatic monocarboxylic acid B). Mixing can be carried out mechanically, for example by stirring, preferably with a suitable stirring device such as a low-speed rotating stirrer, in particular a blade, bar or planetary stirrer or a centrifugal mixer, or a high-speed rotating stirrer, in particular a propeller, turbine, disk or impeller stirrer. It is also possible to carry out mixing hydraulically by continuously pumping the contents of the reactor, in particular with a centrifugal pump.

[0068] The metal azo pigment A) is preferably mixed with at least one aliphatic monocarboxylic acid B) in the form of an aqueous suspension. To prepare such an aqueous suspension, at least one dried, optionally ground metal azo pigment A) is mixed with a sufficient amount of water to prepare a complete suspension of the metal azo pigment.

[0069] However, the metal azo pigments A) can also preferably be used directly in the form of the aqueous reaction mixture as it occurs during the synthesis of the metal azo pigments A).

[0070] For the production of the pigment preparation according to the invention, an aqueous pigment suspension comprising at least one metal azo pigment A) is admixed by stirring with at least one aliphatic monocarboxylic acid B), preferably at a temperature in the range of 60-95 ° C, preferably within a time of 10-60 minutes, and the mixture thus prepared is stirred for preferably 60-240 minutes. The pH of the mixture is then adjusted to a value of 3-7, after which the pigment preparation is isolated using a suction filter or a filter press. The pigment preparation thus obtainable can be dried by conventional drying methods. Suitable drying methods are preferably paddle drying or spray drying of the corresponding aqueous slurry. The pigment preparation can then be milled again.

[0071] The pigment preparation according to the invention may also contain one or more auxiliary agents and / or adjuvants.Preferably, all auxiliary agents and adjuvants that are commonly used in pigment preparations are suitable as auxiliary agents or adjuvants.Particularly preferred is the use of at least one auxiliary agent or adjuvant from the series of surfactants, in particular dispersants, surfactants, wetting agents, emulsifiers, bases and acids.

[0072] Thus, in a preferred embodiment, another subject of the invention is a process for producing a pigment preparation according to the invention, in which at least one metallic azo pigment A) is mixed with at least one aliphatic C 10~22 The monocarboxylic acid B) and optionally one or more auxiliary agents and / or adjuvants are mixed together.

[0073] The surprisingly good filterability (based on the filter pressure value FPV, determined by a pressure filter test according to DIN EN ISO 23900-5:2019-01) and at the same time high tinting strength (determined according to DIN 55986) make the pigment preparation according to the invention ideally suitable for all pigment applications. In particular, the pigment preparation according to the invention is suitable for the mass coloration of synthetic, semi-synthetic or natural polymeric substances, in particular polyvinyl chloride, polystyrene, polyamide, polyethylene or polypropylene, and for the solution coloration of natural, regenerated or synthetic fibers, such as cellulose, polyester, polycarbonate, polyacrylonitrile or polyamide fibers, as well as for the printing of textiles and paper.

[0074] The invention therefore also relates to aliphatic C 2H 2 O 4 pigments for the mass coloring of synthetic, semisynthetic or natural polymeric substances, in particular polyvinyl chloride, polystyrene, polyamide, polyethylene or polypropylene, and for the dope coloring of natural, regenerated or synthetic fibers, such as cellulose, polyester, polycarbonate, polyacrylonitrile or polyamide fibers, and for the printing of textiles and paper. 10~22 The present invention relates to the use of pigment preparations in which the filterability and color strength are improved by the monocarboxylic acid B).

[0075] Preferred Use The present invention preferably comprises the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me in the second metal azo compound (I) 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 , 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+ It is salt. at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me1 The total amount of metal ions Me is 97-100 mol%. 2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or melamine obtainable by reaction of components a) and b), at least one aliphatic C 10~22 The present invention relates to the use of monocarboxylic acids B).

[0076] The present invention particularly preferably comprises the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 90:30 to 10:70; Me in the second metal azo compound (I) 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 , Sm2+ , 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 , 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+ It is salt. at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of metal ions Me is 97-100 mol%. 2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or alternatively melamine obtainable by reaction of components a) and b), at least one aliphatic C 10~22 The present invention relates to the use of monocarboxylic acids B).

[0077] The present invention also particularly preferably relates to a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 40:80 to 20:60; Me in the second metal azo compound (I) 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 , 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+ It is salt. at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of metal ions Me is 97-100 mol%. 2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or alternatively melamine obtainable by reaction of components a) and b), at least one aliphatic C 10~22 The present invention also relates to the use of monocarboxylic acids B).

[0078] In connection with the above uses, the following may be used: n-decanoic acid (CAS No. 334-48-5, capric acid, C 10 H 20 O 2 ), undec-10-enoic acid (CAS No. 112-38-9, undecylenic acid, C 11 H 20 O 2 ), dodecanoic acid (CAS No. 143-07-7, lauric acid, C 12 H 24 O 2 ), Tetradecanoic acid (CAS No. 544-63-8, Myristic acid, C 14 H 28 O 2 ), Hexadecanoic acid (CAS No. 57-10-3, Palmitic acid, C 16 H 32 O 2 ), Octadecanoic acid (CAS No. 57-11-4, Stearic acid, C 18 H 36 O 2 ), (9Z)-Octadec-9-enoic acid (CAS No. 112-80-1, Oleic acid, C 18 H 34 O 2 ) and n-docosanoic acid (CAS No. 112-85-6, behenic acid, C 22 H 44 O 2 At least one aliphatic C 10~22 Particular preference is given to using monocarboxylic acids B).

[0079] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention contain from 14 to 18 carbon atoms and are saturated or monounsaturated.

[0080] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention are tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid) and (9Z)-octadecane-9-enoic acid (oleic acid).

[0081] In the context of the use of the present invention, aliphatic C10~22 The monocarboxylic acids B) can be present in pure form or as mixtures. Such mixtures are known as commercial products of the company Unichema under the trade name "Pristerene®", where the different chemical and quantitative compositions of these mixtures are characterized by a four-digit number code. According to the invention, the following are preferred: Pristerene® 4910, which contains a mixture of 2% by weight of myristic acid, 30% by weight of palmitic acid and 64% by weight of stearic acid, Pristerene® 4911, which contains a mixture of 2% by weight of myristic acid, 45% by weight of palmitic acid and 52% by weight of stearic acid, Pristerene® 4922, which contains a mixture of 0.7% by weight of myristic acid, 30% by weight of palmitic acid and 66% by weight of stearic acid, and Pristerene® 9429.

[0082] Preferred Process The present invention preferably comprises the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me in the second metal azo compound (I) 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 ,Pr3+ 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 , 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+ It is salt. at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of metal ions Me is 97-100 mol%. 2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or alternatively melamine obtainable by reaction of components a) and b), 1. A process for simultaneously improving the filter pressure value FPV (determined by the pressure filter test according to DIN EN ISO 23900-5:2019-01) and the tinting strength (determined according to DIN 55986) of a pigment preparation containing a metal azo pigment A) consisting of 100 to 250 g of at least one aliphatic C per mole of all metal azo compounds (I) contained in the metal azo pigment A) 10~22 The present invention relates to a process by using monocarboxylic acids B).

[0083] The present invention particularly preferably comprises the following: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 90:10 to 30:70; Me in the second metal azo compound (I) 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 , Gd3+ 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 , 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+ It is salt. at least two metal azo compounds of the formula (I) containing, in each case, one mole of the metal ion Me 1 The total amount of metal ions Me is 97-100 mol%. 2 The total amount of is 0 to 3 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or alternatively melamine obtainable by reaction of components a) and b), 1. A process for simultaneously improving the filter pressure value FPV (determined by the pressure filter test according to DIN EN ISO 23900-5:2019-01) and the tinting strength (determined according to DIN 55986) of a pigment preparation containing a metal azo pigment A) consisting of 100 to 250 g of at least one aliphatic C per mole of all metal azo compounds (I) contained in the metal azo pigment A) 10~22 The present invention relates to a process by using monocarboxylic acids B).

[0084] The present invention particularly preferably comprises: a) Formula (I): [ka] (In the formula, R 1 and R 2 is OH, R 3 and R 4 is O, Me in the first metal azo compound (I) 1 Zn 2+ and Ni 2+ and the molar ratio of metal ions Zn:Ni is 40:80 to 20:60; Me in the second metal azo compound (I) 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 , 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+ It is salt. At least two kinds of metal azo compounds (wherein the metal ion Me 1 is in total 99 to 100 mol %, based in each case on 1 mole of all compounds of formula (I), and the metal ions Me 2 The total amount of is 0 to 1 mol%. b) melamine (2,4,6-triamino-1,3,5-triazine, CAS No. 108-78-1) or alternatively melamine obtainable by reaction of components a) and b), 1. A process for simultaneously improving the filter pressure value FPV (determined by the pressure filter test according to DIN EN ISO 23900-5:2019-01) and the tinting strength (determined according to DIN 55986) of a pigment preparation containing a metal azo pigment A) consisting of 100 to 250 g of at least one aliphatic C per mole of all metal azo compounds (I) contained in the metal azo pigment A) 10~22 The present invention relates to a process by using monocarboxylic acids B).

[0085] In the context of the process according to the invention, the following may be used: n-decanoic acid (CAS No. 334-48-5, capric acid, C 10 H 20 O 2 ), undec-10-enoic acid (CAS No. 112-38-9, undecylenic acid, C 11 H 20 O 2 ), dodecanoic acid (CAS No. 143-07-7, lauric acid, C 12 H 24 O 2 ), Tetradecanoic acid (CAS No. 544-63-8, Myristic acid, C 14 H 28 O 2 ), Hexadecanoic acid (CAS No. 57-10-3, Palmitic acid, C 16 H 32 O 2 ), Octadecanoic acid (CAS No. 57-11-4, Stearic acid, C 18 H 36 O 2 ), (9Z)-Octadec-9-enoic acid (CAS No. 112-80-1, Oleic acid, C 18 H 34 O 2 ) and n-docosanoic acid (CAS No. 112-85-6, behenic acid, C 22 H 44 O 2 At least one aliphatic C 10~22 Particular preference is given to using monocarboxylic acids B).

[0086] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention contain from 14 to 18 carbon atoms and are saturated or monounsaturated.

[0087] More preferably, the aliphatic monocarboxylic acids B) contained in the pigment preparation according to the invention are tetradecanoic acid (myristic acid), hexadecanoic acid (palmitic acid), octadecanoic acid (stearic acid) and (9Z)-octadecane-9-enoic acid (oleic acid).

[0088] In the context of the process of the present invention, aliphatic C 10~22 The monocarboxylic acids B) can be present in pure form or as mixtures. Such mixtures are known as commercial products of the company Unichema under the trade name "Pristerene®", where the different chemical and quantitative compositions of these mixtures are characterized by a four-digit number code. According to the invention, the following are preferred: Pristerene® 4910, which contains a mixture of 2% by weight of myristic acid, 30% by weight of palmitic acid and 64% by weight of stearic acid, Pristerene® 4911, which contains a mixture of 2% by weight of myristic acid, 45% by weight of palmitic acid and 52% by weight of stearic acid, Pristerene® 4922, which contains a mixture of 0.7% by weight of myristic acid, 30% by weight of palmitic acid and 66% by weight of stearic acid, and Pristerene® 9429.

[0089] The following examples are intended to illustrate the invention but not to limit it thereto. EXAMPLES

[0090] I. Preparation of Metal-Azobarbituric Melamine Pigments A-W by Prior Art Example 1: Preparation of nickel azobarbituric acid melamine pigment (pigment A) according to EP-A 26 82 435, example 2 (not according to the invention) a) Production of crude pigments 154.1 g (1.0 mol) of diazobarbituric acid and 128.1 g (1.0 mol) of barbituric acid were introduced into 3670 g of distilled water at 85 ° C. The pH was then set to 5 using aqueous potassium hydroxide and the reaction mixture was stirred for 90 minutes. 5000 g of distilled water were added to the azobarbituric acid (1.0 mol) thus prepared at 82 ° C. The pH was then set to 2-2.5 by dropping 33 g of 30% hydrochloric acid and 264.8 g (2.1 mol) of melamine were added. Then 1.0 mol of nickel chloride was dropped in the form of an approximately 25% solution. After 3 hours at 82 ° C, the pH was set to approximately 5.5 by adding potassium hydroxide.

[0091] b) Post-processing For this purpose, the product was diluted with about 330 g of distilled water at 90° C. Then, 70 g of 30% hydrochloric acid were added dropwise and the reaction mixture was stirred for 12 hours at 90° C. The pH of the reaction mixture was then adjusted to about 5 with aqueous potassium hydroxide solution.

[0092] c) Work-up The pigment preparation obtainable from the aftertreatment b) was isolated on a suction filter, washed, dried in a vacuum drying oven at 80° C. and ground in a conventional laboratory mill for about 2 minutes. (Pigment A)

[0093] Examples 2 to 23: Metal-azobarbituric acid melamine pigments B to W Pigments B to W of Examples 2 to 23 listed in Table 1 below were prepared similarly to Example 1, except that instead of 1.0 mol of nickel chloride, a mixture of nickel chloride and zinc chloride in the molar amounts shown in Table 1 was used, and optionally a third metal chloride (Me 2 ) were used, respectively.

[0094] For pigments A to W, tinting strength and filter pressure values ​​were determined as described in Protocols 1 and 2 below and can be found in Table 1.

[0095] [Table 1]

[0096] Examples 24 to 28: Nickel azobarbiturate melamine pigment preparations according to EP-A 1 612 246 (not according to the invention) Preparation Phase 1 63 g of 35% hydrochloric acid was added to 150 g of water with stirring. 30 g of aminoguanidine bicarbonate was introduced into this mixture. After complete dissolution, the mixture was cooled to 0 ° C. Then, 19 g of sodium nitrite was added within 30 minutes, followed by stirring at 0-15 ° C for 30 minutes. Then, amidosulfonic acid was added until the color reaction with potassium iodide starch paper disappeared. Then, 25.6 g of barbituric acid was added and the mixture was heated to 55 ° C and then stirred for 2 hours. Then, 25.6 g of barbituric acid was added and the mixture was heated to 80 ° C and adjusted to pH 5 with sodium hydroxide. After 3 hours, the temperature was allowed to drop to 70 ° C. The reaction product obtained was isolated, washed with hot water and the filter cake was dried at 80 ° C. Yield: 61.4 g of azobarbituric acid disodium salt.

[0097] Preparation Phase 2 63 g of 35% hydrochloric acid was added to 150 g of water with stirring. 38.7 g of benzenesulfonyl hydrazide was introduced into the mixture. The mixture was cooled with ice to below 0 ° C. Then, 19 g of sodium nitrite was added within 30 minutes, followed by stirring at 0-15 ° C for 30 minutes. Amidosulfonic acid was then added until the color reaction with potassium iodide starch paper disappeared. Then, after adjusting the pH to 7.0-9.0 with sodium hydroxide, 25.6 g of barbituric acid was added and the mixture was heated to 50 ° C and then stirred for 2 hours. Then, another 25.6 g of barbituric acid was added, the mixture was heated to 80 ° C and the pH of the mixture was adjusted to 5 with hydrochloric acid. After 3 hours, the temperature was reduced to 70 ° C and the reaction product obtained was isolated and washed with hot water. The filter cake obtained was slurried with 1200 g of water and stirred at 80 ° C for 2 hours. It was then isolated, washed with 2000 g of water at 80° C. until free of benzenesulfonamide and dried at 80° C. Yield: 61.0 g of azobarbituric acid disodium salt.

[0098] Example 24 25 g of azobarbituric acid disodium salt from preparatory step 1 and 0.5 g of oleic acid were introduced into 600 g of water and stirred homogeneously. The pH was then adjusted to 1.0 and the mixture was heated to 95°C. 19.2 g of melamine were then added to the mixture and 18.6 g of nickel chloride hexahydrate, previously dissolved in 115 g of water, were added dropwise over 5 minutes. After 1.5 hours at 90°C, the pH of the mixture was adjusted to 5.5 and stirring was continued for 4 hours. The reaction product was then isolated and washed with hot water until free of salt and melamine. The filter cake was dried at 80°C until the residual moisture content was less than 1.5%. Yield: 42 g of pigment.

[0099] Example 25 25 g of azobarbituric acid disodium salt from preparatory step 1 and 0.5 g of oleic acid were introduced into 600 g of water and stirred homogeneously. The pH was then adjusted to 8.5 and the mixture was heated to 95°C. 19.2 g of melamine were then added to the mixture. After subsequent stirring for 5 minutes, the pH of the mixture was adjusted to 5.0 with hydrochloric acid. Then, after stirring for 5 minutes, 18.6 g of nickel chloride hexahydrate, previously dissolved in 115 g of water, were added dropwise over 10 minutes. After 1.5 hours at 90°C, the pH of the mixture was adjusted to 5.5 and stirring was continued for 4 hours. The reaction product was then isolated and washed with hot water until free of salt and melamine. The filter cake was dried at 80°C until the residual moisture content was less than 1.5%. Yield: 42 g of pigment.

[0100] Example 26 25 g of azobarbituric acid disodium salt from preparatory step 1 and 0.5 g of linoleic acid were introduced into 600 g of water and stirred homogeneously. The pH was then adjusted to 8.5 and the mixture was heated to 95° C. 19.2 g of melamine were then added to the mixture. After subsequent stirring for 5 minutes, the pH of the mixture was adjusted to 5.0 with hydrochloric acid. The mixture was stirred for another 5 minutes, after which 18.6 g of nickel chloride hexahydrate, previously dissolved in 115 g of water, were added dropwise over 10 minutes. After 1.5 hours at 90° C., the pH of the mixture was adjusted to 5.5 and stirring was continued for 4 hours. The reaction product was then isolated and washed with hot water until free of salt and melamine. The filter cake was dried at 80° C. until the residual moisture content was less than 1.5%. Yield: 41.8 g of pigment.

[0101] Example 27 25 g of azobarbituric acid disodium salt from preparatory step 1 and 0.5 g of α-linolenic acid (α-linolenic acid; CAS No. 463-40-1) were introduced into 600 g of water and stirred homogeneously. The pH was then adjusted to 8.5 and the mixture was heated to 95°C. 19.2 g of melamine were then added to the mixture. After subsequent stirring for 5 minutes, the pH of the mixture was adjusted to 5.0 with hydrochloric acid and the mixture was stirred for another 5 minutes before 18.6 g of nickel chloride hexahydrate, previously dissolved in 115 g of water, was added dropwise over 10 minutes. After 1.5 hours at 90°C, the pH of the mixture was adjusted to 5.5 and stirring was continued for 4 hours. The reaction product was then isolated and washed with hot water until free of salt and melamine. The filter cake was dried at 80°C until the residual moisture content was less than 1.5%. Yield: 42 g of pigment.

[0102] Example 28 25 g of azobarbituric acid disodium salt from preparatory step 2 and 0.5 g of oleic acid (CAS No. 112-80-1) were introduced into 600 g of water and stirred homogeneously. The pH was then adjusted to 1.0 and the mixture was heated to 95°C. 19.2 g of melamine were then added to the mixture and 18.6 g of nickel chloride hexahydrate, previously dissolved in 115 g of water, were added dropwise over 5 minutes. After 1.5 hours at 90°C, the pH of the mixture was adjusted to 5.5 and the mixture was stirred for another 4 hours. The reaction product was then isolated and washed with hot water until free of salt and melamine. The filter cake was dried at 80°C until the residual moisture content was less than 1.5%. Yield: 41.4 g of pigment.

[0103] [Table 2]

[0104] Tinting strength compared to Example 1 II. Manufacturing of pigment preparations Example 29: Preparation of pigment preparation A-1 (not according to the invention) The aqueous suspension of pigment A as obtained after step c) of Example 1 was mixed with 100 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation A-1).

[0105] Examples 30 to 45: Preparation of pigment preparations A-2 to A-17 (not according to the invention) In examples 30 to 45, pigment preparations A-2 to A-17 not according to the invention were prepared analogously to example 29. In each case, the aqueous suspension of pigment A as obtained after step c) of example 1 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 2.

[0106] Determination of tint strength and filter pressure values For pigment preparations A-1 to A-17, the tint strength and filter pressure values ​​compared to Pigment A were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 3.

[0107] [Table 3]

[0108] Example 46: Preparation of pigment preparation B-1 (not according to the invention) The aqueous suspension of pigment B as obtained after step c) of Example 2 was mixed with 50 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried in a vacuum drying oven at 80° C. and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation B-1).

[0109] Examples 47 to 93: Preparation of pigment preparations B-2 to B-48 (not according to the invention) In examples 47 to 93, pigment preparations B-2 to B-48 not according to the invention were prepared analogously to example 46. In each case, an aqueous suspension of pigment B as obtained after step c) of example 2 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 4.

[0110] Determination of tint strength and filter pressure values For pigment preparations B-1 to B-48, the tinting strength and filter pressure values ​​compared to Pigment B were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 4.

[0111] [Table 4]

[0112] [Table 5]

[0113] Example 94: Preparation of pigment preparation C-1 (not according to the invention) The aqueous suspension of pigment C as obtained after step c) of Example 3 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. Afterwards the pH was set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried in a vacuum drying oven at 80° C. and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation C-1).

[0114] Examples 95 to 136: Preparation of pigment preparations C-2 to C-44 (not according to the invention) In examples 95 to 137, similarly to example 94, pigment preparations C-2 to C-44 not according to the invention were prepared. In each case, the aqueous suspension of pigment C as obtained after step c) of example 3 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 5.

[0115] Measurement of color strength and filter pressure values For pigment preparations C-1 to C-44, the tint strength and filter pressure values ​​compared to Pigment C were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 5.

[0116] [Table 6]

[0117] [Table 7]

[0118] Example 138: Preparation of pigment preparation D-1 (not according to the invention) An aqueous suspension of pigment D as obtained after step c) of Example 4 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation D-1).

[0119] Examples 139 to 171: Preparation of pigment preparations D-2 to D-34 (not according to the invention and according to the invention) In examples 139 to 171, pigment preparations according to the invention and not according to the invention were prepared analogously to example 138. In each case, an aqueous suspension of pigment D as obtained after step c) of example 4 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 5.

[0120] Determination of tint strength and filter pressure values For pigment preparations D-1 to D-34, the tinting strength and filter pressure values ​​compared to Pigment D were determined according to the following protocols 1 and 2. These values ​​can also be found in Table 6.

[0121] [Table 8]

[0122] Example 172: Preparation of pigment preparation E-1 (not according to the invention) The aqueous suspension of pigment E as obtained after step c) of Example 5 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried in a vacuum drying oven at 80° C. and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation E-1).

[0123] Examples 173 to 240: Preparation of pigment preparations E-2 to E-70 (not according to the invention and according to the invention) In examples 173 to 240, pigment preparations E-2 to E-81 according to the invention and not according to the invention were prepared analogously to example 172. In each case the aqueous suspension of pigment E obtained after step c) of example 5 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 7.

[0124] Determination of tint strength and filter pressure values For pigment preparations E-1 to E-70, the tinting strength and filter pressure values ​​compared to Pigment E were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 7.

[0125] [Table 9]

[0126] [Table 10]

[0127] [Table 11]

[0128] Example 241: Preparation of pigment preparation F-1 (not according to the invention) The aqueous suspension of pigment F as obtained after step c) of Example 6 was mixed with 70 g of Pristerene 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried in a vacuum drying oven at 80° C. and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation F-1).

[0129] Examples 242 to 274: Preparation of pigment preparations F-2 to F-33 (not according to the invention and according to the invention) In examples 242 to 274, pigment preparations F-2 to F-33 according to the invention and not according to the invention were prepared analogously to example 242. In each case the aqueous suspension of pigment F obtained after step c) of example 6 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 8.

[0130] Determination of tint strength and filter pressure values For pigment preparations F-1 to F-33, tinting strength and filter pressure values ​​compared to pigment F were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 8.

[0131] [Table 12]

[0132] Example 275: Preparation of pigment preparation G-1 (not according to the invention) The aqueous suspension of pigment G as obtained after step c) of Example 7 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation G-1).

[0133] Examples 276 to 355: Preparation of pigment preparations G-2 to G-81 (not according to the invention and according to the invention) In examples 276 to 355, pigment preparations G-2 to G-81 according to the invention and not according to the invention were prepared analogously to example 275. In each case, the aqueous suspension of pigment G as obtained after step c) of example 7 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 9.

[0134] Determination of tint strength and filter pressure values For pigment preparations G-1 to G-81, the tint strength and filter pressure values ​​compared to Pigment G were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 9.

[0135] [Table 13]

[0136] [Table 14]

[0137] [Table 15]

[0138] Example 356: Preparation of pigment preparation H-1 (not according to the invention) The aqueous suspension of pigment H obtained after step c) of Example 8 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation H-1).

[0139] Examples 357 to 436: Preparation of pigment preparations H-2 to H-81 (not according to the invention and according to the invention) In examples 357 to 436, pigment preparations H-2 to H-81 according to the invention and not according to the invention were prepared analogously to example 356. In each case, the aqueous suspension of pigment H as obtained after step c) of example 8 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 10.

[0140] Measurement of color strength and filter pressure values For pigment preparations H-1 to H-81, the tint strength and filter pressure values ​​compared to pigment H were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 10.

[0141] [Table 16]

[0142] [Table 17]

[0143] [Table 18]

[0144] Example 437: Preparation of pigment preparation I-1 (not according to the invention) The aqueous suspension of pigment I as obtained after step c) of Example 9 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation I-1).

[0145] Examples 438 to 468: Preparation of pigment preparations I-2 to I-32 (not according to the invention and according to the invention) In examples 438 to 468, pigment preparations I-2 to I-32 according to the invention and not according to the invention were prepared analogously to example 437. In each case, the aqueous suspension of pigment I as obtained after step c) of example 9 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 11.

[0146] Measurement of color strength and filter pressure values For pigment preparations I-1 to I-32, the tinting strength and filter pressure values ​​compared to Pigment I were determined according to protocols 1 and 2 below. These values ​​can also be found in Table 11.

[0147] [Table 19]

[0148] [Table 20]

[0149] Example 469: Preparation of pigment preparation J-1 (not according to the invention) An aqueous suspension of pigment J as obtained after step c) of Example 10 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation J-1).

[0150] Examples 470 to 500: Preparation of pigment preparations J-2 to J-32 (not according to the invention and according to the invention) In examples 469 to 500, pigment preparations J-2 to J-32 according to the invention and not according to the invention were prepared analogously to example 469. In each case, the aqueous suspension of pigment J as obtained after step c) of example 10 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 2.

[0151] Measurement of color strength and filter pressure values For pigment preparations J-1 to J-32, the tint strength and filter pressure values ​​compared to Pigment I were determined according to protocols 1 and 2 below. These values ​​can also be found in Table 12.

[0152] [Table 21]

[0153] Example 501: Preparation of pigment preparation K-1 (not according to the invention) The aqueous suspension of pigment K as obtained after step c) of Example 11 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation K-1).

[0154] Examples 502 to 532: Preparation of pigment preparations K-2 to K-32 (not according to the invention and according to the invention) In examples 502 to 532, pigment preparations K-2 to K-32 according to the invention and not according to the invention were prepared analogously to example 501. In each case, the aqueous suspension of pigment K as obtained after step c) of example 11 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 13.

[0155] Determination of tint strength and filter pressure values For pigment preparations K-1 to K-32, the tinting strength and filter pressure values ​​compared to pigment K were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 13.

[0156] [Table 22]

[0157] Example 533: Preparation of pigment preparation L-1 (not according to the invention) An aqueous suspension of pigment L as obtained after step c) of Example 12 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation L-1).

[0158] Examples 534 to 563: Preparation of pigment preparations L-2 to L-32 (not according to the invention) In examples 531 to 561, pigment preparations L-2 to L-32 not according to the invention were prepared analogously to example 530. In each case, an aqueous suspension of pigment L as obtained after step c) of example 12 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 14.

[0159] Measurement of color strength and filter pressure values For pigment preparations L-1 to L-32, the tinting strength and filter pressure values ​​compared to pigment L were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 14.

[0160] [Table 23]

[0161] Example 565: Preparation of pigment preparation M-1 (not according to the invention) The aqueous suspension of pigment M as obtained after step b) of Example 13 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation M-1).

[0162] Examples 566 to 593: Preparation of pigment preparations M-2 to M-32 (not according to the invention) In examples 563 to 593, pigment preparations M-2 to M-32 according to the invention and not according to the invention were prepared analogously to example 565. In each case, the aqueous suspension of pigment M as obtained after step b) of example 13 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 15.

[0163] Determination of tint strength and filter pressure values For pigment preparations M-1 to M-32, the tinting strength and filter pressure values ​​compared to pigment M were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 15.

[0164] [Table 24]

[0165] Example 594: Preparation of pigment preparation N-1 (not according to the invention) The aqueous suspension of pigment N as obtained after step b) of Example 14 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation N-1).

[0166] Examples 595 to 597: Preparation of pigment preparations N-2 to N-32 (not according to the invention) In examples 595 to 625, pigment preparations N-2 to N-32 according to the invention and not according to the invention were prepared analogously to example 594. In each case, the aqueous suspension of pigment N as obtained after step b) of example 14 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 16.

[0167] Determination of tint strength and filter pressure values For pigment preparations N-1 to N-32, the tinting strength and filter pressure values ​​compared to Pigment N were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 16.

[0168] [Table 25]

[0169] Example 626: Preparation of pigment preparation O-1 (not according to the invention) The aqueous suspension of pigment O as obtained after step b) of Example 11 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation O-1).

[0170] Examples 627 to 657: Preparation of pigment preparations O-2 to O-32 (not according to the invention) In examples 627 to 657, inventive and non-inventive pigment preparations O-2 to O-32 were prepared analogously to example 626. In each case, an aqueous suspension of pigment O as obtained after step b) of example 15 was mixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 17.

[0171] Determination of tint strength and filter pressure values For pigment preparations O-1 to O-32, the tinting strength and filter pressure values ​​compared to Pigment O were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 17.

[0172] [Table 26]

[0173] Example 658: Preparation of pigment preparation P-1 (not according to the invention) The aqueous suspension of pigment P as obtained after step b) of Example 16 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation P-1).

[0174] Examples 659 to 689: Preparation of pigment preparations P-2 to P-32 (not according to the invention and according to the invention) In examples 659 to 689, pigment preparations P-2 to P-32 according to the invention and not according to the invention were prepared analogously to example 658. In each case, the aqueous suspension of pigment P as obtained after step b) of example 16 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 18.

[0175] Determination of tint strength and filter pressure values For pigment preparations P-1 to P-32, the tinting strength and filter pressure values ​​compared to Pigment P were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 18.

[0176] [Table 27]

[0177] Example 690: Preparation of pigment preparation Q-1 (not according to the invention) The aqueous suspension of pigment Q as obtained after step b) of Example 17 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation Q-1).

[0178] Examples 691 to 721: Preparation of pigment preparations Q-2 to Q-32 (not according to the invention and according to the invention) In examples 691 to 721, pigment preparations Q-2 to Q-32 according to the invention and not according to the invention were prepared analogously to example 690. In each case, the aqueous suspension of pigment Q as obtained after step b) of example 17 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 19.

[0179] Determination of tint strength and filter pressure values The tinting strength and filter pressure values ​​of pigment preparations Q-1 to Q-32 compared to Pigment Q were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 19.

[0180] [Table 28]

[0181] Example 722: Preparation of pigment preparation R-1 (not according to the invention) The aqueous suspension of pigment R as obtained after step b) of Example 18 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation R-1).

[0182] Examples 723 to 753: Preparation of pigment preparations R-2 to R-32 (not according to the invention and according to the invention) In examples 723 to 753, pigment preparations R-2 to R-32 according to the invention and not according to the invention were prepared analogously to example 722. In each case, the aqueous suspension of pigment R as obtained after step b) of example 18 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 20.

[0183] Determination of tint strength and filter pressure values For pigment preparations R-1 to R-32, the tinting strength and filter pressure values ​​compared to pigment R were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 20.

[0184] [Table 29]

[0185] Example 754: Preparation of pigment preparation S-1 (not according to the invention) An aqueous suspension of pigment S as obtained after step b) of Example 19 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation S-1).

[0186] Examples 754 to 784: Preparation of pigment preparations S-2 to S-32 (not according to the invention and according to the invention) In examples 754 to 784, pigment preparations S-2 to S-32 according to the invention and not according to the invention were prepared analogously to example 727. In each case, the aqueous suspension of pigment S as obtained after step b) of example 19 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 21.

[0187] Measurement of color strength and filter pressure values For pigment preparations S-1 to S-32, tint strength and filter pressure values ​​compared to Pigment S were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 21.

[0188] [Table 30]

[0189] Example 785: Preparation of pigment preparation T-1 (not according to the invention) An aqueous suspension of pigment T as obtained after step b) of Example 20 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation T-1).

[0190] Examples 786 to 816: Preparation of pigment preparations T-2 to T-32 (not according to the invention and according to the invention) In examples 785 to 816, pigment preparations T-2 to T-32 according to the invention and not according to the invention were prepared analogously to example 785. In each case, the aqueous suspension of pigment T as obtained after step b) of example 20 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 22.

[0191] Determination of tint strength and filter pressure values For pigment preparations T-1 to T-32, the tint strength and filter pressure values ​​compared to Pigment T were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 22.

[0192] [Table 31]

[0193] Example 817: Preparation of pigment preparation U-1 (not according to the invention) The aqueous suspension of pigment U as obtained after step b) of Example 21 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation U-1).

[0194] Examples 817 to 848: Preparation of pigment preparations U-2 to U-32 (not according to the invention and according to the invention) In examples 817 to 848, pigment preparations U-2 to U-32 according to the invention and not according to the invention were prepared analogously to example 793. In each case, the aqueous suspension of pigment U as obtained after step b) of example 21 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 23.

[0195] Measurement of color strength and filter pressure values For pigment preparations U-1 to U-32, the tinting strength and filter pressure values ​​compared to Pigment U were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 23.

[0196] [Table 32]

[0197] Example 849: Preparation of pigment preparation V-1 (not according to the invention) The aqueous suspension of pigment U as obtained after step b) of Example 22 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation V-1).

[0198] Examples 850 to 880: Preparation of pigment preparations V-2 to V-32 (not according to the invention and according to the invention) In examples 850 to 880, pigment preparations V-2 to V-32 according to the invention and not according to the invention were prepared analogously to example 849. In each case, the aqueous suspension of pigment V as obtained after step b) of example 22 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 24.

[0199] Determination of tint strength and filter pressure values For pigment preparations V-1 to V-32, the tinting strength and filter pressure values ​​compared to Pigment V were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 24.

[0200] [Table 33]

[0201] Example 881: Preparation of pigment preparation W-1 (not according to the invention) The aqueous suspension of pigment W as obtained after step b) of Example 23 was mixed with 70 g of Pristerene® 4910 and stirred for 60 minutes. The pH was then set to 5 using aqueous potassium hydroxide solution. The pigment preparation was then isolated on a suction filter, washed, dried at 80° C. in a vacuum drying oven and ground in a conventional laboratory mill for about 2 minutes (=pigment preparation W-1).

[0202] Examples 882 to 913: Preparation of pigment preparations W-2 to W-32 (not according to the invention and according to the invention) In examples 882 to 913, pigment preparations W-2 to W-32 according to the invention and not according to the invention were prepared analogously to example 881. In each case, the aqueous suspension of pigment W as obtained after step b) of example 23 was admixed with different amounts of various aliphatic carboxylic acids B) or mixtures thereof, as shown in table 25.

[0203] Determination of tint strength and filter pressure values The tinting strength and filter pressure values ​​of pigment preparations W-1 to W-32 compared to Pigment W were determined according to protocols 1 and 2 shown below. These values ​​can also be found in Table 25.

[0204] [Table 34]

[0205] [Table 35]

[0206] [Table 36]

[0207] The pigments produced according to Examples 1 to 22 and the pigment preparations produced according to Examples 23 to 913 were each subjected to the determination of the tinting strength according to DIN 55986 (see Protocol 1) and the determination of the filter pressure value according to DIN EN ISO 23900-5:2019-01 (see Protocol 2).

[0208] Determination of color strength in PVC: Protocol 1 As test medium, a plasticized PVC compound was prepared by homogenizing 67.5% Vestolit® E7004 (Vestolit GmbH), 29.0% Hexamoll® DINCH (BASF), 2.25% Baerostab UBZ 770 (Baerlocher GmbH) and 1.25% Isocolor white pigment paste (ISL-Chemie) in a laboratory dissolver.

[0209] 100g of PVC compound was heated at 150°C for 20min on a laboratory roll mill. -1 and 18 min -1 The pigment was applied to two 150 mm diameter rolls rotating at 100 rpm. After rolling, rolled sheets were produced together with 0.10 g of pigment, which were then guided to pass through the 0.10 mm roll nip eight times. The uniformly colored rolled sheets were removed after passing through the 0.8 mm roll nip and laid smoothly on a metal surface. The cooled rolled sheets were then cooled for 26 min. -1 and 24 min -1The coating was applied eight times between two unheated 110 mm diameter rolls rotating at 100° C. through a roll nip of 0.2 mm. To smooth the surface, the resulting rolled sheet was again applied to the rolls at 150° C., removed at 0.8 mm, placed on a smooth surface, and allowed to cool. Relative tinting strength was measured using test pieces of this rolled sheet.

[0210] The relative color strength was calculated after remission measurements of the test specimens against a white background using a spectrophotometer with measurement geometry d / 8 under standard illuminant D65 and a 10° observer, according to DIN 55986, using the sum of the K / S values ​​over the visible spectrum ranging from 400 nm to 700 nm.

[0211] Determination of the filter pressure value (FPV) by pressure filter testing according to DIN EN ISO 23900-5:2019-01 (measurement of the pressure rise): Protocol 2 1950 g of polyamide 6 (Durethan® B30S from LANXESS Deutschland GmbH, Cologne) doped with 1% titanium dioxide was intensively mixed with 50 g of the pigment to be tested in a tumble mixer for 1 hour. The mixture was extruded at 225° C. and 700 rpm in a Leistritz ZSE 18HP twin-screw extruder. 200 g of the granulate thus produced were filtered through a 25 μm filter at a temperature of 238° C. and the resulting pressure rise was measured. The pressure difference between the initial pressure and the maximum pressure was used to calculate the filter pressure value FPV. The lower this pressure rise (measured in bar / g), the better the filtration properties of the pigment preparation to be tested.

[0212] Conclusion: From the measurement results shown in Tables 1 to 25 it can be seen that only the pigment preparations according to the invention have both improved filtration properties and improved color strength compared to the pigment preparations not according to the invention.

Claims

1. i) Below: a) a compound of formula (I) in which at least the metal ion Me is different: 【Chemistry 1】 (In the formula, R １ and R ２ are each independently OH, NH ２ or N.H.R. ５ and R ３ and R ４ are each independently O or NR ５ and R ５ is hydrogen or alkyl, preferably C １ ~C ４ is alkyl, Me is a metal ion Me in the first metal azo compound. １ and a metal ion Me in the second metal azo compound. ２ and Where: Me １ is Zn ２＋ and Ni ２＋ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me ２ is 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＋ 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＋ (It is) or tautomers thereof, provided that, in each case based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me １ The amount of Me is 97 to 100 mol % in total. ２ The amount of metal ions selected from the series is 0-3 mol % in total; b) Formula (II) 【Chemistry 2】 (In the formula, R ６ is independently in each occurrence hydrogen or alkyl, preferably C １ ~C ４ alkyl, which may be substituted one or more times with OH; or a reaction product of (I) and (II), A) a metallic azo pigment comprising: ii) 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A). １０～２２ Monocarboxylic acid B) A pigment preparation comprising:

2. 2. The pigment preparation according to claim 1, characterized in that in the metal azo pigment A) the ratio of metal azo compound (I) to compound of formula (II) is 1 mol:0.05-4 mol, preferably 1 mol:0.5-2.5 mol, more preferably 1 mol:1.0-2.0 mol.

3. In formula (I), R １ and R ２ is OH, R ３ and R ４ is O, and Me in the first metal azo compound is Me １ Zn ２＋ and Ni ２＋ wherein the molar ratio of metal ions Zn:Ni is 90:10 to 30:70, and Me in the second metal azo compound is Me ２ It is called Me ２ is Al ３＋ ２／３ , Fe ２＋ , Fe ３＋ ２／３ , Co ２＋ , Co ３＋ ２／３ , Ce ３＋ ２／３ , Mg ２＋ , Ca ２＋ , Sr ２＋ , La ３＋ ２／３ , Mg ２＋ , Mn ２＋ , Nd ２＋ , Nd 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＋ , Ca ２＋ Or Ba ２＋ 3. The pigment preparation according to claim 1, wherein b) is melamine or a reaction product of a compound of formula (I) with melamine.

4. The aliphatic C １０～２２ The monocarboxylic acid B) is a saturated or mono- to tri-unsaturated carboxylic acid, preferably at least one C carboxylic acid from the series capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, behenic acid. １０～２２ 4. The pigment preparation according to claim 1, wherein the pigment is a monocarboxylic acid.

5. The aliphatic C １０～２２ 5. The pigment preparation according to claim 4, characterized in that the monocarboxylic acids B) are present in pure form or as mixtures, preferably mixtures containing myristic acid, palmitic acid or stearic acid.

6. below: a) a compound of formula (I) in which at least the metal ion Me is different: 【Chemistry 3】 (In the formula, R １ and R ２ are each independently OH, NH ２ or N.H.R. ５ and R ３ and R ４ are each independently O or NR ５ and R ５ is hydrogen or alkyl, preferably C １ ~C ４ is alkyl, Me is a metal ion Me in the first metal azo compound. １ and a metal ion Me in the second metal azo compound. ２ and Where: Me １ is Zn ２＋ and Ni ２＋ and the molar ratio of metal ions Zn:Ni is 97:3 to 3:97; Me ２ is 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＋ , 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＋ (It is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me １ The amount of Me is 97 to 100 mol % in total. ２ The amount of metal ions selected from the series is 0-3 mol % in total; b) Formula (II) 【Chemistry 4】 (In the formula, R ６ is independently in each occurrence hydrogen or alkyl, preferably C １ ~C ４ alkyl, which may be substituted one or more times by OH; or a reaction product of (I) and (II), At least one aliphatic C １０～２２ Use of monocarboxylic acids B), 100 to 250 g of the aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A). １０～２２ Monocarboxylic acids B) are used.

7. 7. Use according to claim 6, characterized in that in the metal azo pigment A) the ratio of metal azo compound (I) to compound of formula (II) is 1 mol:0.05-4 mol, preferably 1 mol:0.5-2.5 mol, more preferably 1 mol:1.0-2.0 mol.

8. In formula (I), R １ and R ２ is OH, R ３ and R ４ is O, and Me in the first metal azo compound is Me １ Zn ２＋ and Ni ２＋ wherein the molar ratio of metal ions Zn:Ni is 90:10 to 30:70, and Me in the second metal azo compound is Me ２ It is called Me ２ is Al ３＋ ２／３ , Fe ２＋ , Fe ３＋ ２／３ , Co ２＋ , Co ３＋ ２／３ , Ce ３＋ ２／３ , Mg ２＋ , Ca ２＋ , Sr ２＋ , La ３＋ ２／３ , Mg ２＋ , Mn ２＋ , Nd ２＋ , Nd 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＋ , Ca ２＋ Or Ba ２＋ 8. Use according to claim 6 or 7, characterized in that b) is melamine or a reaction product of formula (I) with melamine.

9. The aliphatic C １０～２２ The monocarboxylic acid B) is a saturated or mono- to tri-unsaturated carboxylic acid, preferably at least one C from the series of capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid and behenic acid. １０～２２ Use according to any one of claims 6 to 8, characterized in that it is a monocarboxylic acid.

10. The aliphatic C １０～２２ 10. Use according to claim 9, characterized in that the monocarboxylic acids B) are present in pure form or as mixtures, preferably mixtures containing myristic acid, palmitic acid or stearic acid.

11. below: a) a compound of formula (I) in which at least the metal ion Me is different: 【Chemistry 5】 (In the formula, R １ and R ２ are each independently OH, NH ２ or N.H.R. ５ and R ３ and R ４ are each independently O or NR ５ and R ５ is hydrogen or alkyl, preferably C １ ~C ４ is alkyl, Me in the first metal azo compound is Me １ Zn ２＋ and Ni ２＋ where the molar ratio of metal ions Zn:Ni is from 97:3 to 3:97; Me in the second metal azo compound is Me ２ It is called Al ３＋ ２／３ , Fe ２＋ , Fe ３＋ ２／３ , Co ２＋ , Co ３＋ ２／３ , La ３＋ ２／３ , Ce ３＋ ２／３ , P 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 , 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＋ (It is) or tautomers thereof, provided that in each case, based on 1 mole of all compounds of formula (I), at least two metal azo compounds of the metal ion Me １ The amount of Me is 97 to 100 mol % in total. ２ The amount of metal ions selected from the series is 0-3 mol % in total; b) Formula (II) 【Chemistry 6】 (In the formula, R ６ is independently in each occurrence hydrogen or alkyl, preferably C １ ~C ４ alkyl, which may be substituted one or more times by OH; or a reaction product of (I) and (II), 1. A process for simultaneously improving the filter pressure value FPV (determined by the pressure filter test according to DIN EN ISO 23900-5:2019-01) and the color strength (determined according to DIN 55986) of a pigment preparation containing a metal azo pigment A) consisting of 100 to 250 g of at least one aliphatic C per mole of all the metal azo compounds (I) contained in the metal azo pigment A) １０～２２ The process by using monocarboxylic acid B).

12. 12. The process according to claim 11, characterized in that in the metal azo pigment A) the ratio of metal azo compound (I) to compound of formula (II) is 1 mol:0.05-4 mol, preferably 1 mol:0.5-2.5 mol, more preferably 1 mol:1.0-2.0 mol.

13. In formula (I), R １ and R ２ is OH, R ３ and R ４ is O, and Me in the first metal azo compound is Me １ Zn ２＋ and Ni ２＋ wherein the molar ratio of metal ions Zn:Ni is 90:10 to 30:70, and Me in the second metal azo compound is Me ２ It is called Me ２ is Al ３＋ ２／３ , Fe ２＋ , Fe ３＋ ２／３ , Co ２＋ , Co ３＋ ２／３ , Ce ３＋ ２／３ , Mg ２＋ , Ca ２＋ , Sr ２＋ , La ３＋ ２／３ , Mg ２＋ , Mn ２＋ , Nd ２＋ , Nd 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＋ , Ca ２＋ Or Ba ２＋ 13. The process according to claim 11 or 12, characterized in that b) is melamine or a reaction product of formula (I) with melamine.

14. The aliphatic C １０～２２ The monocarboxylic acid B) is a saturated or mono- to tri-unsaturated carboxylic acid, preferably at least one C from the series of capric acid, undecylenic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid and behenic acid. １０～２２ The process according to any one of claims 11 to 13, characterized in that the carboxylic acid is a monocarboxylic acid.

15. The aliphatic C １０～２２ 15. The process according to claim 14, characterized in that the monocarboxylic acids B) are present in pure form or as mixtures, preferably mixtures containing myristic acid, palmitic acid or stearic acid.

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