UNIVERSAL DISPERSANTS FOR INORGANIC AND ORGANIC PIGMENTS

Description

[0001] The present invention relates to water-based preparations or dispersions of inorganic and organic pigments, processes for their preparation and their use for coloring natural and synthetic materials of all kinds, in particular coating materials, paints, varnishes, glazes, wood protection systems and inks.

[0002] Inorganic pigments consist primarily of minerals or metal salts such as chromates, metal oxides, sulfates, sulfides, carbonates, and cyanides. They are widely used in industry due to their lightfastness and low cost. Organic pigments, on the other hand, are typically composed of carbon rings and chains, exhibiting a brighter, richer color and higher tinting strength. Both pigment types are solid particles, but due to their different nature, they have different surface chemistries. To use pigments in the formulations described above, specific surface-active substances such as wetting and dispersing agents must be used to modify the surface chemistry and enable good dispersion of the pigment particles.According to the known particle stabilization mechanisms, the wetting and dispersing aids used enable good steric and / or electrostatic stabilization of the dispersed particles in these application media without flocculation or reagglomeration of the pigment particles.

[0003] There is a need to provide aqueous pigment preparations for the above-mentioned applications that meet the high technical requirements, particularly with regard to particle size distribution, compatibility and miscibility with the respective application medium, coloristic properties, pigment content, rheology profile and stability.

[0004] The tendency towards foaming, which also meets regulatory requirements, for example with regard to the toxicological and ecotoxicological profile, is an increasing challenge for the industry.

[0005] The main reason for this is that the progressive tightening of chemicals legislation and the awarding of environmental labels, such as the Blue Angel or the European Ecolabel, mean that more and more common formulation components for pigment preparations can no longer be used, or can only be used to a limited extent for certain applications. This applies in particular to wetting and dispersing agents. For example, alkylphenol ethoxylates (APEOs) are bioaccumulative and hormonal degradation products that are now strictly regulated and prohibited for many applications. The use of tristyrylphenol ethoxylates (TSPEOs) is still possible, but there is a strong trend in industry to avoid TSPEOs due to their adverse ecotoxicological profile.The use of novolak- or bisphenol A-based dispersants, which were used in the past, is limited for the same reasons. The use of oxyalkylated reaction products based on primary and secondary amines as dispersants is also critical for some applications due to regulatory and technical reasons and is therefore only possible to a limited extent.

[0006] The prior art describes aqueous pigment preparations containing various dispersing agents, which are claimed to have a universal effect for organic or inorganic pigments.

[0007] US-5340394 describes pigment concentrates based on polyethylene glycol polyethers with low molecular weights of 200 to 700 in combination with non-ionic alkyl glycoside surfactants.

[0008] WO-2020 / 152093 teaches aqueous pigment preparations comprising (A) at least one organic and / or inorganic pigment and / or filler (B) at least one dispersant of the formula (I) or (II), or mixtures of the dispersants of the formulas (I) and (II), where n is an integer greater than or equal to 1, preferably 1 to 5, particularly preferably 1 to 2, z is an integer greater than or equal to 1, preferably 1 to 10, particularly preferably 1 to 4, R1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms or a hydrogen atom or the structural unit -OX or the structural unit -CH2-OX, and structural unit X corresponds to the formula (III).

[0009] DE-10 2005 019 384 teaches a polymer of formula (I), where: R1: each independently of one another is H, or an alkyl group having 1 to 6 carbon atoms; R2: H, an alkyl group having 1 to 8 carbon atoms, an alkali ion, an alkaline earth ion, an ammonium ion or the residue of any other base; R3: an aryl group or an aralkyl group having 6 to 18 carbon atoms; R4, R5: H or an alkyl group having 1 to 6 carbon atoms; R6, R7: each independently: H or methyl; R8, R9: H or any terminal group; a: 0.1 to 0.9; b: 0.9 to 0.1; c: 0.001 to 0.5; m: 1 to 4; n: 1 to 150. The polymer according to the invention is particularly suitable as a dispersant for pigments or fillers in paints.

[0010] DE-930655U1 teaches an aqueous non-clogging tinting paint for paints or similar coating compositions, which tinting paint has a viscosity of 0.05 to 1.5 Ns / m 2 (i.e. 0.5 to 15 poise and preferably 1 to 12 poise) at 20°C and contains solid pigment particles dispersed in a dispersant system consisting of a mixture of water and a water-miscible non-volatile micellizing dispersant having hydrophilic moieties and moieties (usually less hydrophilic than the hydrophobic moieties) capable of adsorbing onto the surface of the pigment, wherein a) the dispersant system also contains a minor amount (of less than 50 wt% and preferably less than 30 wt%, based on the weight of the dispersant system) of a non-volatile macromolecular non-micellizing auxiliary material having a weight average molecular weight of 230 (preferably 250) to 4500, which is selected from i) liquids miscible with the mixture of water and the non-volatile dispersant, and / or ii) particulate organic solids having a melting point below 150°C which are soluble or dispersible in the system, b) for a selected weight of pigment, the weight ratio of the non-volatile micellizing dispersant to the pigment is at least 5% (and preferably 15%) greater than the weight ratio of the non-volatile micellizing dispersant to the pigment which, at the Daniel Pour Point of a Reference tinting color would be present,which consists only of the same pigment, water and the same non-volatile micellising dispersant, c) the flowability of the tinting colour is such that, after the non-clogging tinting colour has been kept at 25°C for 18 hours in a cylindrical bore with a diameter of 2 mm and a length of 15 mm at an ambient relative humidity of 50%, a pressure of not more than 320 MN / m 2 is sufficient to cause the remaining tinting colour to flow out of the bore, and d) "non-volatile" means a vapour pressure below 1.3 N / m 2 (and preferably below 1.0 N / m 2 ) at 25°C.

[0011] EP-1092756 teaches a pigment preparation containing a pigment and / or carbon black and a polymer and / or a surfactant selected from the group consisting of crosslinked polyoxyethyleneacrylic acid, fatty alcohol polyglycol ethers, polyvinylpyrrolidones, alcohol alkoxylates, ligninsulfonates, alkylphenol polyglycol ethers, naphthalenesulfonic acid derivatives, or mixtures thereof, which is produced by freeze-drying from an aqueous dispersion. They can be used for coloring and / or antistatic treatment in water-based paint and varnish systems, emulsion paints, printing inks, ink systems, and coating systems.

[0012] WO-2009 / 145285 teaches a recording ink comprising a colorant dispersion comprising: a coloring agent and water, wherein the dispersant is a polycarboxylic acid dispersant containing units represented by the formulas (1) to (3): wherein R 1< , R 2< and R 4< are selected from a hydrogen atom and CH 3 ; R 3< is selected from a hydrogen atom and a C 1 -C 3 alkyl group; R 5< represents a C 1 -C 3 alkyl group; AO and BO represent a C 2 -C 3 oxyalkylene group; M is selected from alkali metal, alkaline earth metal, ammonium and organic amine; m is an integer from 1 to 30; and n is an integer from 5 to 50, and wherein the colorant is any one of a black pigment, a magenta pigment, a cyan pigment and a yellow pigment.

[0013] US-7659340 teaches pigment pastes using a surfactant mixture comprising at least one alkyd-compatible surfactant and at least one latex-compatible surfactant.

[0014] WO-2014 / 000842 describes aqueous pigment preparations containing fatty acid condensation products and non-ionic surfactants as dispersing agents.

[0015] US-2018 / 244925 teaches pigment formulations containing water-soluble, non-ionic, surface-active copolymers based on carboxylic acid esters and / or carboxamides and a phosphoric or phosphoric acid surfactant as a dispersing agent.

[0016] The prior art indicates that universal dispersing properties can only be achieved when water-soluble surfactants are used as a component of the pigment formulation. However, such water-soluble surfactants have a low molecular weight, can easily migrate to the surface of coatings, and are therefore often prone to surfactant leaching when used in aqueous coating compositions such as water-based paints. Such leaching is visible on the surface of drying or dried paints as vertical marks (commonly known as "snail trails") under cold and humid atmospheres. On the other hand, Gabel (European Coatings Journal 02-2019, pp. 90-94) demonstrated that polymeric dispersants are less prone to leaching due to their higher molecular weight and chemical structure.

[0017] This is caused by their usual multiple adhesion points on the pigment surface and their lower mobility within the paint and coating formulation due to slower Brownian molecular motion and entanglement of the polymer chains with other paint and coating components.

[0018] It is very clear that, despite the described state of the art, there is still a need for universal dispersing agents for pigment formulations with improved performance. The pigment formulations should exhibit the highest possible color strength. Furthermore, they should remain stable even during extended storage and be non-thixotropic.

[0019] It has now been surprisingly found that a combination of two polymeric dispersants can achieve stable, universal formulations of inorganic and / or organic pigments that exhibit the desired properties in the above-mentioned coloring applications, in particular easy dispersibility and high color strength at low formulation viscosities. Furthermore, it has been surprisingly found that the combination of two polymeric dispersants exhibits synergistic effects in pigment preparations that are not obtained from the individual components.

[0020] The present invention firstly relates to a pigment preparation comprising (A) at least one organic and / or inorganic pigment and / or filler; (B) at least one anionic copolymer as a dispersant, which contains (I) 40 to 95 mol% of structural units of an anionic monomer selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, 2-carboxyethylacrylic acid, maleic acid, mixtures thereof and their respective salts, preferably methacrylic acid or its salt, and (II) 5 to 60 mol% of structural units of a monomer having repeating units according to formula (B1) wherein R11, R12, R13 are independently selected from the group consisting of H, methyl, ethyl, R4H or an alkyl group having 1 to 4 carbon atoms, X is selected from the group consisting of O, COO, CONH, CH2O or CH2CH2O, Y is an ethylene group, Z is a propylene group, a butylene group or a phenylethylene group, m is an integer from 0 to 100, n is an integer from 1 to 100, and m + n is greater than 5, and (C) at least one nonionic copolymer which contains at least one structural unit with aromatic groups and at least one structural unit with polyethylene glycol groups, and (H) water.

[0021] The pigment preparation according to the invention may optionally also contain the following further components: (D) wetting agents, (E) further surfactants and / or dispersants, (F) one or more organic solvents and / or one or more hydrotropic substances and / or mixtures thereof, and (G) further additives customary for the preparation of aqueous pigment dispersions.

[0022] Preferred pigment preparations contain 5 to 80 wt.%, preferably 10 to 70 wt.%, particularly preferably 30 to 70 wt.% of component (A).

[0023] Preferred pigment preparations contain 0.1 to 30 wt.%, preferably 1 to 20 wt.%, particularly preferably 2 to 15 wt.% of component (B).

[0024] Preferred pigment preparations contain 0.1 to 30 wt.%, preferably 1 to 20 wt.%, particularly preferably 2 to 15 wt.% of component (C).

[0025] Preferred pigment preparations contain water to 100 wt.%.

[0026] Particularly preferred pigment preparations contain components in the following proportions: (A) 5 to 80 wt.%, in particular 10 to 70 wt.%, (B) 0.1 to 30 wt.%, in particular 1 to 20 wt.%, (C) 0.1 to 30 wt.%, in particular 1 to 20 wt.%, (D) 0 to 10 wt.%, in particular 0.1 to 5 wt.%, (E) 0 to 20 wt.%, in particular 1 to 10 wt.%, (F) 0 to 30 wt.%, in particular 5 to 20 wt.%, (G) 0 to 20 wt.%, in particular 0.1 to 5 wt.%, each based on the total weight (100 wt%) of the pigment preparation.

[0027] In the event that the pigment preparation according to the invention contains one or more of the components (D), (E), (F) and (G), their minimum concentration is, independently of one another, preferably at least 0.01% by weight, in particular at least 0.1%, based on the total weight of the pigment preparation. Component (A)

[0028] Component (A) of the pigment preparation according to the invention is a finely divided organic or inorganic pigment or a filler or a mixture of various organic and / or inorganic pigments and / or fillers. Component (A) can also be a dye that is soluble in certain solvents and pigmented in other solvents. The pigments can be used both in the form of a dry powder and as a water-moist presscake.

[0029] The organic pigments used are preferably Monoazo, disazo, lacquered azo, β-naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments and polycyclic pigments such as phthalocyanine, quinacridone, perylene, perinone, thioindigo, anthanthrone, anthronone, anthraquinone, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, isoindoline and diketopyrrolopyrrole pigments or carbon blacks; carbon black pigments such as gas or furnace blacks;Monoazo and disazo pigments, in particular the color index pigments Pigment Yellow 1, Pigment Yellow 3, Pigment Yellow 12, Pigment Yellow 13, Pigment Yellow 14, Pigment Yellow 16, Pigment Yellow 17, Pigment Yellow 73, Pigment Yellow 74, Pigment Yellow 81, Pigment Yellow 83, Pigment Yellow 87, Pigment Yellow 97, Pigment Yellow 111, Pigment Yellow 126, Pigment Yellow 127, Pigment Yellow 128, Pigment Yellow 155, Pigment Yellow 174, Pigment Yellow 176, Pigment Yellow 191, Pigment Yellow 213, Pigment Yellow 214, Pigment Yellow 219, Pigment Red 38, Pigment Red 144, Pigment Red 214, Pigment Red 242, Pigment Red 262, Pigment Red 266, Pigment Red 269, Pigment Red 274, Pigment Orange 13, Pigment Orange 34 or Pigment Brown 41;β-naphthol and naphthol AS pigments, in particular the color index pigments Pigment Red 2, Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 9, Pigment Red 12, Pigment Red 14, Pigment Red 53:1, Pigment Red 112, Pigment Red 146, Pigment Red 147, Pigment Red 170, Pigment Red 184, Pigment Red 187, Pigment Red 188, Pigment Red 210, Pigment Red 247, Pigment Red 253, Pigment Red 256, Pigment Orange 5, Pigment Orange 38 or Pigment Brown 1; lacquered azo and metal complex pigments, in particular the color index pigments Pigment Red 48:2, Pigment Red 48:3, Pigment Red 48:4, Pigment Red 57:1, Pigment Red 257, Pigment Orange 68 or Pigment Orange 70; Benzimidazoline pigments, in particular the color index pigments Pigment Yellow 120, Pigment Yellow 151, Pigment Yellow 154, Pigment Yellow 175, Pigment Yellow 180, Pigment Yellow 181, Pigment Yellow 194, Pigment Red 175, Pigment Red 176, Pigment Red 185, Pigment Red 208, Pigment Violet 32, Pigment Orange 36, Pigment Orange 62, Pigment Orange 72 or Pigment Brown 25;Isoindolinone and isoindoline pigments, in particular the color index pigments Pigment Yellow 139 or Pigment Yellow 173; phthalocyanine pigments, in particular the color index pigments Pigment Blue 15, Pigment Blue 15:1, Pigment Blue 15:2, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue 15:6, Pigment Blue 16, Pigment Green 7 or Pigment Green 36; Anthanthrone, anthraquinone, quinacridone, dioxazine, indanthrone, perylene, perinone and thioindigo pigments, in particular the color index pigments Pigment Yellow 196, Pigment Red 122, Pigment Red 149, Pigment Red 168, Pigment Red 177, Pigment Red 179, Pigment Red 181, Pigment Red 207, Pigment Red 209, Pigment Red 263, Pigment Blue 60, Pigment Violet 19, Pigment Violet 23 or Pigment Orange 43; Triarylcarbonium pigments, in particular the color index pigments Pigment Red 169, Pigment Blue 56 or Pigment Blue 61;Diketopyrrolopyrrole pigments, in particular the color index pigments Pigment Red 254, Pigment Red 255, Pigment Red 264, Pigment Red 270, Pigment Red 272, Pigment Orange 71, Pigment Orange 73, Pigment Orange 81. ;

[0030] Also suitable are lacquered dyes such as Ca, Mg and Al lacquer pigments of dyes containing sulfonic acid and / or carboxylic acid groups.

[0031] Suitable inorganic pigments include titanium dioxide, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, manganese titanium rutile, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed-phase pigments, rare earth sulfides, zinc and cobalt spinels with nickel, iron- and chromium-based spinels with copper-zinc, as well as manganese, bismuth vanadates, and mixed pigments. In particular, the color index pigments Pigment Yellow 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Brown 24, Pigment Red 101, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 17, Pigment Black 11, Pigment Black 33, and Pigment White 6 are used. Mixtures of inorganic pigments are often preferred. Mixtures of organic and inorganic pigments are also commonly used.

[0032] Suitable fillers include, for example, finely divided ores, minerals, and sparingly or insoluble salts such as carbonates, calcium carbonate, dolomite, silicon dioxide, quartz, cristobalite, diatomaceous earth, silicates, aluminum silicates, silicic acids, talc, kaolin, mica, feldspar, and barium sulfate. Filler mixtures are also often preferred. Mixtures of organic and / or inorganic pigments with fillers are also frequently used. Formulations containing only one or more fillers are used, for example, for blending pigment preparations to adjust the desired property profile, such as pigment content, rheology, density, or compatibility. Component (B)

[0033] (B) is an anionic copolymer containing at least the structural units (I) and (II).

[0034] In a preferred embodiment, the structural unit (I) of (B) is acrylic acid or methacrylic acid, or salts thereof, particularly preferably methacrylic acid or salts thereof.

[0035] In general, the proportion of structural units (I) is from 40 to 95 mol%, preferably from 45 to 85 mol%.

[0036] In a preferred embodiment, salts of the structural unit (I) of (B) are alkali salts, in particular sodium or potassium salts, and ammonium salts.

[0037] The structural unit (II) of (B) corresponds to formula (B1). Generally, the proportion of structural units (II) is from 5 to 60 mol%, preferably from 15 to 55 mol%.

[0038] In formula (B1), R11, R12, and R13 are preferably independently selected from the group consisting of H or methyl. R12 is particularly preferably methyl. R11 and R13 are particularly preferably H.

[0039] In formula (B1), R4 is preferably H or a methyl group. R4 is particularly preferably H.

[0040] In formula (B1), X is preferably O or C(O)O. Particularly preferably, X is C(O)O and R12 is methyl.

[0041] In formula (B1), Z preferably represents propylene and phenylethylene. With a phenylethylene group, the structural unit (ZO) corresponds to formula (2)

[0042] In formula (B1), m represents an integer from 0 to 100, preferably an integer from 1 to 10, particularly preferably from 2 to 5, such as 3 or 4.

[0043] In formula (B1), n ​​represents an integer from 1 to 100, preferably an integer from 5 to 45. More preferably, n represents an integer from 8 to 14.

[0044] In formula (B1), (m+n) preferably represents an integer from 8 to 49. More preferably, (m+n) represents an integer from 11 to 18. Component (C)

[0045] Component (C) is a nonionic copolymer containing at least one structural unit with aromatic groups and at least one structural unit with polyoxyethylene groups. Component (C) acts as a dispersant for inorganic or organic pigments.

[0046] In a preferred embodiment, the copolymer (C) comprises, in addition to at least one structural unit with polyoxyethylene groups, a structural unit with aromatic groups derived from styrene oxide.

[0047] Particularly preferred are copolymers (C) as described in WO-2020 / 152093. In this particularly preferred embodiment, the copolymers (C) correspond to formula (3), formula (4), or mixtures thereof where no integer greater than or equal to 1, preferably equal to 1 R 1< is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms, a hydrogen atom, the structural unit -OX, or the structural unit -CH 2 -OX, preferably a hydrogen atom, X corresponds to formula (5) wherein o is an integer from 1 to 50, preferably an integer from 1 to 4, p is an integer from 1 to 200, preferably an integer from 10 to 25, and (o+p) is greater than 2, preferably an integer from 2 to 250.

[0048] Particularly preferably, (o+p) is an integer from 11 to 29.

[0049] Particularly preferred are copolymers (C) of styrene and maleic anhydride modified with polyetheramines, as described in DE-102007032185. In this particularly preferred embodiment, the copolymers (C) correspond to formula (6) wherein q is an integer from 1 to 4, particularly preferably an integer from 1 to 2, an integer from 5 to 50, particularly preferably an integer from 5 to 20, R5 is H or an alkyl group having 1 to 4 carbon atoms, particularly preferably methyl, t is an integer from 0 to 10, particularly preferably an integer from 1 to 4, u is an integer from 1 to 100, particularly preferably an integer from 10 to 50, and t + u is greater than 10.

[0050] Due to their non-ionic properties, copolymers of type (C) can be used almost exclusively for organic pigment formulations and often do not work for inorganic pigments. Component (D)

[0051] Component (D) can be, for example, cationic, anionic, amphoteric, or non-ionic compounds that promote pigment wetting (wetting agents). These are preferably so-called substrate wetting or flow control agents based on fluorosurfactants, modified fluoroacrylates, or organically modified silicones. Component (E)

[0052] Component (E) of the pigment preparations according to the invention comprises conventional dispersants and surfactants or mixtures of such substances suitable for preparing aqueous pigment dispersions. Typically, anionic, cationic, amphoteric, or nonionic surfactants are used for this purpose. It has proven particularly successful for dispersants to have one or more medium- or long-chain hydrocarbon chains or several hydrocarbon chains with aromatic ring groups. Examples of these are alkyl sulfates such as lauryl sulfate, stearyl sulfate, or octadecyl sulfate; primary alkylsulfonates such as dodecylsulfonate; and secondary alkylsulfonates, in particular the C13-C17 alkanesulfonate sodium salt; alkyl phosphates; alkylbenzenesulfonates such as dodecylbenzenesulfonic acid; and all salts of these compounds.Also suitable as component (E) of the pigment preparations according to the invention are soy lecithin and condensation products of fatty acids and taurine or hydroxyethanesulfonic acid, as well as alkoxylation products of castor oil resin esters, fatty alcohols, fatty amines, fatty acids and fatty acid amides.

[0053] These alkoxylation products can also be ionic and contain, as end groups, for example, sulfosuccinic acid half-esters, sulfonic acid, sulfuric acid, and phosphoric acid esters and their salts, sulfonates, sulfates, or phosphates. Also suitable are nonionic copolymers prepared using macromonomers from polyethylene glycol mono(meth)acrylic acid esters or polypropylene glycol mono(meth)acrylic acid esters, and similarly, anionically modified block copolymers consisting of styrene oxide and polyalkylene oxide units. Component (F)

[0054] Component (F) corresponds to organic solvents, hydrotropes, or retention aids that act as solubilizers or increase the resistance to drying. These can be, for example, the following compounds or a mixture thereof: monohydric or polyhydric alcohols, their ethers and esters, for example alkanols, in particular with 1 to 4 carbon atoms, such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol; di- or trihydric alcohols, in particular with 2 to 5 carbon atoms, e.g.Ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,6,6-hexanetriol, glycerin, diethylene glycol, dipropylene glycol, triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol; lower alkyl ethers of polyhydric alcohols, such as ethylene glycol monomethyl, ethyl or butyl ether, triethylene glycol monomethyl or ethyl ether; ketones and ketone alcohols such as acetone, methyl ethyl ketone, diethyl ketone, methyl isobutyl ketone, methyl pentyl ketone, cyclopentanone, cyclohexanone, diacetone alcohol; copolymers of ethylene and propylene glycol. Component (G)

[0055] Component (G) comprises a range of different additives, such as rheology-modifying additives or anti-settling agents, which have a beneficial effect on viscosity and rheology. Compounds such as polyvinyl alcohol and cellulose derivatives can be used as viscosity regulators. Water-soluble natural or synthetic resins and polymers can also be considered as film formers or binders to increase adhesion and abrasion resistance. Organic or inorganic bases and acids are used as pH regulators. Preferred organic bases are amines, e.g., ethanolamine, diethanolamine, triethanolamine, N,N-dimethylethanolamine, diisopropylamine, aminomethylpropanol, or dimethylaminomethylpropanol. Preferred inorganic bases are sodium hydroxide, potassium hydroxide, lithium hydroxide, or ammonia.Fats and oils of plant and animal origin can also correspond to component (G), for example, beef tallow, palm kernel fat, coconut fat, rapeseed oil, sunflower oil, linseed oil, palm oil, soybean oil, peanut oil, whale oil, cottonseed oil, corn oil, poppyseed oil, olive oil, castor oil, safflower oil, soybean oil, herring oil, and sardine oil. Saturated and unsaturated fatty acids are also more common additives; for example, palmitic acid, capric acid, myristic acid, lauric acid, stearic acid, oleic acid, linoleic acid, linolenic acid, caproic acid, caprylic acid, arachidic acid, behenic acid, palmitoleic acid, gadolic acid, erucic acid, and ricinoleic acid, as well as their salts, are used as pigment surface modifiers.

[0056] Furthermore, light stabilizers such as derivatives of benzotriazole, camphor, hydroxybenzophenone, hydroxyphenyltriazine, oxalanilide, salicylic acid, or cinnamic acid, and radical scavengers such as hindered-amine light stabilizers (HALS) can be used. Derivatives based on tetramethylpiperidine are used, as are antioxidants based on citric acid. Component G can also include defoamers based on mineral oil or silicone derivatives. Component (H)

[0057] Water, component (H), used to prepare the pigment preparations is preferably used in the form of distilled or deionized water. Drinking water (tap water) and / or water of natural origin may also be used.

[0058] The pigment preparations exhibit high color strength and low foaming tendency. They have a viscosity of less than 1.0 Pas, preferably less than 0.7 Pas, and particularly preferably less than 0.5 Pas. The pigment preparations can be mixed with alcohols of various chain lengths, preferably ethanol, in any ratio without coagulation or flocculation of the pigment particles. The pigment preparations exhibit good storage stability.

[0059] Furthermore, the pigment preparations according to the invention can be produced free from alkylphenol, tristyrylphenol, novolak and bisphenol A derivatives as well as from primary and secondary amines.

[0060] The present invention also relates to a process for the preparation of such pigment preparations by initially introducing component (A) in the form of powder, granules or aqueous presscake in the presence of water (H) and components (B) and (C), and optionally dispersing with (D), (E), (F) and (G), and optionally diluting the resulting aqueous pigment dispersion with water (H). The pigment and the mixtures of components (B) and (C) are dispersed using a dispersing unit or combinations of different dispersing units, preferably a stirred ball mill operated at a stirrer peripheral speed of 10 m / s and under the action of non-metallic grinding media having a diameter of less than or equal to 1.2 mm, preferably less than or equal to 0.8 mm, which are finely dispersed or finely dispersed in the presence of water.The other additives may be present and / or added subsequently during the dispersion step.

[0061] The invention also relates to the use of the pigment preparations according to the invention as dyes for pigmenting and coloring natural and synthetic materials of all kinds, in particular aqueous coating materials, paints, emulsions and lacquers (water-based lacquers), water-dilutable lacquers, glazes, varnishes and wood protection systems, printing inks, here for example textile printing, flexographic printing, decorative printing or gravure inks, electrophotographic toners and developers, such as one- or two-component powder toners (also referred to as one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners, inks, preferably inkjet inks, e.g. on an aqueous or non-aqueous basis ("solvent-based"), microemulsion inks, UV-curable inks and those inks that work according to the hot melt process, inks for writing utensils such as colored pencil leads, fiber pens, fineliners,Felt-tip pens, gel rollers, text or whiteboard markers, and insulating materials such as glass wool.

[0062] Furthermore, the pigment preparations according to the invention are suitable for coloring macromolecular materials of all kinds, e.g., natural and synthetic fiber materials. Other applications include the coloring of sausage casings, seeds, fertilizers, glass, especially glass bottles, plasters, concrete, wood stains, waxes, paraffins, inks, pastes for pens, chalks, detergents and cleaning agents, shoe care products, latex products, abrasives for viscose spin-dyeing, and for the coloring of plastics or high-molecular-weight materials of all kinds.High molecular weight organic materials are, for example, cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins such as polymerization resins or condensation resins, for example aminoplasts, in particular urea and melamine formaldehyde resins, alkyd resins, acrylic resins, phenolic resins, polycarbonates, polyolefins such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid esters, polyamides, polyurethanes or polyesters, rubber, casein, latices, silicone, individually or in a mixture.

[0063] Furthermore, the pigment preparations according to the invention can also be used as colorants for color filters ("color filters") for "flat screens" for both additive and subtractive color generation, also for "photoresists" and as dyes for electronic inks ("electronic inks" or "e-inks") or electronic paper ("electronic paper" or "e-paper"). Definitions

[0064] "Water-soluble" refers to a material that, at a concentration of 0.1 wt% at 25°C, has sufficient solubility to produce a solution that is clear to the eye. The term "water-insoluble" refers to a material that is not "water-soluble."

[0065] "Monomer" means a discrete, unpolymerized chemical unit that, in the presence of an initiator or a suitable reaction, produces a macromolecule, such as free radical polymerization. "Unit" means a monomer that has already been polymerized, i.e., is part of a polymer.

[0066] "Polymer" means a chemical formed from the polymerization of one, two, or more monomers. The term "polymer" encompasses all materials derived from the polymerization of monomers, as well as natural polymers. Polymers made from only one type of monomer are called homopolymers. A polymer contains at least two monomer units. Polymers formed from two or more different types of monomers are called copolymers. The distribution of the different monomers can be random, alternating, or block-like. The latter then forms so-called "block copolymers." When the main chain of an existing polymer is functionalized with another different polymer, so-called "comb copolymers" or "graft copolymers" are formed. The term "polymer" as used here encompasses any type of polymer, including homopolymers and copolymers. Abbreviations

[0067] CI"Color Index" nmNot measurable NTNot thixotropic, pigment preparation shows Newtonian behavior LTSlightly thixotropic, pigment preparation shows slight non-Newtonian behavior TThixotropic, pigment preparation shows clear non-Newtonian behavior Examples Components of the exemplary pigment preparations Component (A) Organic pigments

[0068] A1 Hansa Brilliant Yellow 2GX 70-S (CI Pigment Yellow 74, PY 74) A2 Novoperm ®< Yellow HR 03 LV 5462 (CI Pigment Yellow 83, PY 83) A3 Hostaperm ®< Violet RL 02 (CI Pigment Violet 23, PV 23) A4 Permanent Red FGR (CI Pigment Red 112, PR 112) A6 Hostaperm ®< Red D3G 70 (CI Pigment Red 254, PR 254) A7 Hostaperm ®< Blue A4R (CI Pigment Blue 15:1, PB 15:1) A8 Hostaperm ®< Blue B2G-EDS VP3491 (CI Pigment Blue 15:3, PB 15:3) A9 Hostaperm ®< Green GNX (CI Pigment Green 7, PG 7) A10 Printex ®< 300 (CI Pigment Black 7, PBk 7) Inorganic pigments

[0069] A11 Bayferrox ®< 3920 (CI Pigment Yellow 42, PY 42) A12 Sicopal®< Orange L 2430 (CI Pigment Orange 82, PO 82) A13 Sicopal ®< Yellow L 1100 (CI Pigment Yellow 184, PY 184) A14 Bayferrox ®< Red 130M (CI Pigment Red 101, PR 101) A15 Kronos ®< 2160 (CI Pigment White 6, PW 6) Dispersant component (B)

[0070] B Statistical copolymer consisting of 49 mol% methacrylic acid and 51 mol% polyglycol MA750 Dispersant component (C)

[0071] C1 Branched block copolymer consisting of 1 mol% glycerol and 14 mol% styrene oxide and 85 mol% ethylene oxide (according to WO-2020152093) C2 Graft copolymer consisting of the reaction product of a styrene / maleic anhydride copolymer (Cray Valley SMA 2000, ratio 2:1 styrene to maleic anhydride) with one equivalent of Jeffamine M-2005 (Huntsman) Comparison dispersant

[0072] VD1 Nuosperse® FX 600 (Elementis), a multifunctional polymeric dispersant recommended for both inorganic and organic pigments. Nuosperse FX 600 is a polymaleic acid ammonium salt, described in EP1599549B1. VD2 Dispex® Ultra 4290 (BASF), a high-molecular-weight dispersant suitable for inorganic and organic pigments in aqueous preparations. Dispex Ultra 4290 is a high-molecular-weight dispersant / copolymer with an acid number of 9 mg KOH / g, presumably based on polyacrylate. VD3 Dispersogen ®< LFS (Clariant), a dispersant containing anionic surfactants for water-based pigment preparations, suitable for all pigments. VD4 Dispersogen ®< ECS (Clariant), a dispersant containing anionic surfactants for water-based pigment preparations, suitable for all pigments. VD5 Tego ®< Dispers 750 W (Evonik) is a weakly anionic polymeric wetting and dispersing additive for high-quality aqueous formulations. It is highly compatible and suitable for all pigment types, especially inorganic pigments.

[0073] The pigment preparations were prepared either in a Lau Disperser or in a Dispermat. Production of a pigment preparation in the Lau Disperser:

[0074] The liquid components (deionized water, dispersant, additives) were homogenized using a shaker (e.g., Heidolph Unimax 2010). The pigment, either as a powder, granules, or presscake, was then homogenized and predispersed together with the liquid premix using a paint shaker (e.g., Lau Disperser DAS). The subsequent fine dispersion was performed using a paint shaker (e.g., Lau Disperser DAS), with grinding being carried out with glass beads of size d = 3 mm for a defined running time of 60 minutes. The grinding media were separated using a centrifuge (e.g., Heraeus Multifuge 3s), and the pigment preparation was isolated. Production of a pigment preparation in the Dispermat:

[0075] The pigment, either as a powder, granules, or presscake, was homogenized and predispersed together with the dispersants and other additives in deionized water using a dissolver (e.g., VMA Getzmann GmbH, type AE3-M1) or other suitable device. Subsequent fine dispersion was performed using a bead mill (e.g., using an AE3-M1 from VMA-Getzmann GmbH) or other suitable dispersing unit, with grinding being carried out with zirconium silicate or zirconium oxide beads of size d = 1.2–1.4 mm to achieve the desired color strength, color, and transparency. The dispersion was then adjusted to the desired final pigment concentration with deionized water, the grinding media were separated, and the pigment preparation was isolated.

[0076] The pigment preparations described in the following examples (Tables 1 and 2) were prepared by the process described above, using the respective components in the amounts indicated to obtain 100 parts of the respective pigment preparation. In all examples, parts are parts by weight. Characterization of a pigment preparation:

[0077] The viscosity was determined using a cone-plate viscometer (MCR 72) from Anton Paar GmbH at 20 °C (titanium cone: diameter 60 mm, 1°). The viscosity dependence on shear rate was measured in a range between 0 and 200 s -1<. The viscosity of each sample was evaluated at a shear rate of 60 s -1<.

[0078] The color strength was determined using spectral measurements. A 2% tint of the pastes was prepared in a white emulsion paint. The tint was applied to a test substrate using a film-coating doctor blade with a gap height of 120 µm and dried overnight. The color values ​​of the color strips were measured using a spectrophotometer. The color strength was calculated from the measured color values ​​according to ISO 787-26.

[0079] To assess the storage stability of the dispersions, the viscosity was measured immediately after preparation and after 14 days of storage at 50 °C. In addition, the color strength of the sample stored in this manner was determined against a sample stored at room temperature. Furthermore, the homogeneity and sedimentation behavior of the stored sample were evaluated by determining the sediment and serum formed. Evaluation:

[0080] The evaluation is based on the following four parameters: thixotropy, stability, viscosity, and color strength. The classification was carried out as described below: Thixotropy: NT = Not Thixotropic, the paste does not develop any structure or viscosity, i.e. it does not become more viscous or even solid under storage conditions. LT = Slightly Thixotropic, the paste develops an increased viscosity during storage or even becomes non-flowable. However, the paste can be liquefied again with the application of a small amount of energy, for example in the form of shearing. T = Thixotropic, the paste solidifies under storage conditions and is no longer flowable, but becomes temporarily flowable again with the application of increased energy. Stability: 3 = The paste remains homogeneous even over a period of storage and does not form serum or sedimentation. 2 = Over the storage period, the paste forms easily stirrable serum on the surface or sediment at the bottom. 1 = Over the storage period, the paste forms two phases or forms a sediment at the bottom that is difficult or impossible to stir.Viscosity: The viscosity assessment depends heavily on the pigment being dispersed. The general goal is to produce a flowable pigment paste. Its viscosity is typically in the target range between 50 and 1000 mPa*s. Color strength: The color values ​​were measured after 14 days of storage against the values ​​of a reference product. Color strengths above 100% are better than the reference. The exception is white pigment pastes, where values ​​below 100% are better than the reference. Summary assessment is based on the following 4 levels:

[0081] Better: All parameters within the desired range (at least -OK), but better than standard dispersants (standard dispersants used: Dispersogen LFS for organic and carbon black pigments, Dispersogen ECS for inorganic pigments). OK: All parameters within the desired range, comparable to standard dispersants. Almost OK (~OK): One parameter is not met (preparations often show slight thixotropy and are slightly weaker in color than preparations made with standard dispersants). Not OK (NOK): At least two parameters are not met (preparations show high viscosity and stability problems and are significantly weaker in color than preparations made with standard dispersants). Table 1: Results of the pigment pastes Example pigment pigment concentration in parts by weight Dispersant in parts by weight Thixotropy stability Viscosity (mPa*s) Color strength after 14 days Evaluation 1(V) A1 50 6 VD5 NT 1 283 96,7 NOK 2(V) A1 50 6 VD1 T 3 3058 77,7 NOK 3(V) A1 50 6 VD2 NT 3 347 96,9 OK 5 A1 50 5,5 B + 1,0 C2 NT 3 631 120,6 Better 6 A1 50 2,2 B + 1,8 C1 NT 3 166 105,8 Better 7(V) A2 35 8 VD5 nm nm nm nm NOK, Coagulated 8(V) A2 35 8 VD1 NT 3 105 88,0 ~OK 9(V) A2 35 8 VD2 NT 2 123 99,2 ~OK 10 A2 35 6 B + 2 C2 NT 3 90 92,8 OK 11 A2 35 6,8 B + 1,2 C2 NT 3 92 91 OK 12 A2 35 4,4 B + 3,6 C1 NT 3 71 93,7 OK 13(V) A7 35 8 VD5 nm nm nm nm NOK, coagulated 14(V) A7 35 8 VD1 NT 2 55 74,6 NOK 15(V) A7 35 8 VD2 NT 3 218 84,1 OK 16 A7 35 6B+2 C2 NT 3 450 86,3 OK 17 A7 35 6,8 B + 1,2 C2 NT 3 478 89,5 OK 18 A7 35 4,4 B + 3,6 C1 NT 3 359 87,0 OK 19(V) A8 45 6 VD5 nm nm nm nm NOK, coagulated 20(V) A8 45 6 VD1 T 3 2492 78,6 NOK 21(V) A8 45 6 NT 3 175 74,1 ~OK 22 A8 45 5,5 B + 1,0 C2 NT 3 274 82,6 OK 23 A8 45 3,6 B + 2,9 C1 NT 3 274 79,1 OK 24(V) A3 30 7 VD5 T 3 956 74,6 NOK 25(V) A3 30 7 VD1 NT 2 29 89,0 ~OK 26(V) A3 30 7 VD2 NT 2 37 84,2 ~OK 27 A3 30 5,5 B + 1,0 C2 NT 3 89 84,3 OK 28 A3 30 3,6 B + 2,9 C1 NT 3 136 87,7 OK 29(V) A9 40 6 VD5 nm nm nm nm NOK, coagulated 30(V) A9 40 6 VD1 T 3 253 79,0 ~OK 31(V) A9 40 6 VD2 NT 1 145 91,3 NOK 32 A9 40 6 B + 2 C2 NT 3 894 79,6 OK 33 A9 40 5,1 B + 0,9 C2 NT 3 631 80,3 OK 34 A9 40 4,4 B + 3,6 C1 NT 3 582 81,9 OK 35(V) M 45 6 VD5 NT 1 268 59,5 NOK 36(V) M 45 6 VD1 T 3 652 82,0 ~OK 37(V) A4 45 6 VD2 NT 3 311 63,7 ~OK 38 M 45 4,5 B + 1,5 C2 NT 3 891 80,6 OK 39 A4 45 5,1 B + 0,9 C2 NT 3 932 81,8 OK 40 A4 45 3,3 B + 2,7 C1 NT 3 799 89,3 OK 41(V) A10 35 7 VD5 nm nm nm nm NOK, coagulated 42(V) A10 35 7 VD1 NT 2 453 83,8 ~OK 43(V) A10 35 7 VD2 NT 3 70 91,0 OK 44 A10 35 5,5 B + 1 C2 NT 3 77 91,2 OK 45 A10 35 3,6 B + 2,9 C1 NT 3 68 92,3 OK 46(V) A14 60 4 VD5 NT 1 nm nm NOK 47(V) A14 60 4 VD1 T 3 336 99,7 ~OK 48(V) A14 60 4 VD2 NT 1 nm nm NOK 49 A14 65 3 B + 1 C2 NT 2 237 106,5 better 50 A14 65 3,4 B + 0,6 C2 NT 2 191 106,5 better 51 A14 65 2,2 B + 1,8 C1 NT 2 148 105,9 better 52(V) A11 55 6 VD5 nm nm nm nm NOK, coagulated 53(V) A11 55 6 VD1 nm nm nm nm NOK, coagulated 54(V) A11 55 6 VD2 NT 2 179 100,1 ~OK 55 A14 55 1,7 B + 1,3 C2 NT 3 265 101,9 better 56 A11 55 2,6 B + 0,4 C1 NT 3 299 99,8 better 57(V) A15 65 4 VD5 NT 1 225 109,8 NOK 58(V) A15 65 6 VD5 NT 2 327 113,8 better 59(V) A15 65 4 VD1 T 3 635 107,1 ~OK 60(V) A15 65 4 VD2 nm nm nm nm NOK 61(V) A15 65 6 VD2 NT 1 350 114,2 NOK 62 A15 65 4,5 B + 1,5 C2 NT 2 372 114,6 better 63 A15 65 3,4 B + 0,6 C2 NT 2 169 111,4 better 64 A15 65 5,5 B + 1 C2 LT 3 443 112,7 better 65 A15 65 3,6 B + 2,9 C1 NT 3 350 111,5 better

[0082] To all examples in Table 1, 10.0 parts of component (E, propylene glycol), 0.2 parts of component (F preservative), 0.3 parts of component (G, defoamer) and balancing component (H, deionized water) were added.

[0083] The numerical values ​​from the examples in Table 1 clearly show the improved and, above all, universal performance of the mixtures according to the invention compared to known universal dispersants that are commercially available. Examples 133-135

[0084] Table 2: Synergetic effects of pigment pastes Example pigment pigment concentration in parts by weight Dispersant in parts by weight Thixotropy stability Viscosity (mPa*s) Color strength after 14 days Evaluation 66(V) A1 50 6 C2 NT 3 459 91,3 OK 67(V) A1 50 6 C1 NT 3 399 98,3 OK 68(V) A1 50 6 B NT 2 12030 75,4 NOK 5 A1 50 5,5 B + 1,0 C2 NT 3 631 120,6 Better 6 A1 50 2,2 B + 1,8 C1 NT 3 166 105,8 Better 69(V) A4 45 6 C2 NT 3 293 74,5 ~OK 70(V) A4 45 6 C1 NT 3 172 87,4 OK 71(V) A4 45 6 B NT 3 381 62,0 NOK 38 A4 45 4,5 B + 1,5 C2 NT 3 891 80,6 OK 39 A4 45 5,1 B + 0,9 C2 NT 3 932 81,8 OK 40 A4 45 3,3 B + 2,7 C1 NT 3 799 89,3 OK 72(V) A10 35 7 C2 NT 3 83 86,7 ~OK 73(V) A10 35 7 C1 NT 3 59 82,7 ~OK 74(V) A10 35 7 B NT 3 83 75,9 -OK 44 A10 35 5,5 B + 1 C2 NT 3 77 91,2 OK 45 A10 35 3,6 B + 2,9 C1 NT 3 68 92,3 OK 75(V) A11 55 6 C2 LT 3 1220 96,2 ~OK 76(V) A11 55 6 C1 nm nm nm nm NOK 77(V) A11 55 6 B NT 2 293 95,6 ~OK 55 A14 55 1,7 B + 1,3 C2 NT 3 265 101,9 better 56 A11 55 2,6 B + 0,4 C1 NT 3 299 99,8 better

[0085] The numerical values ​​from the examples in Table 2 clearly demonstrate that the mixtures according to the invention also have synergistic effects that were not foreseeable from the individual components. For example, the pigment preparation of the organic pigment Yellow PY 74 (A1) with B2 exhibited strong incompatibility and high viscosity. Preparations containing C2 were rated OK but showed slight color weakness. A mixture of B2 / C2 in a mass ratio of 85 / 15 results in a stable pigment preparation with very low viscosity and very good compatibility, along with greatly improved color strength. Similar synergistic effects can be observed with other organic pigments such as Pigment Red PR 112 (A4), carbon black (A10), and the inorganic pigment PY 42 (A11).

Claims

1. Pigment preparation comprising (A) at least one organic and / or inorganic pigment and / or filler; (B) at least one anionic copolymer as dispersant, which contains (I) 40 to 95 mol% of structural units of an anionic monomer which is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, 2-carboxyethylacrylic acid, maleic acid, mixtures thereof and their respective salts, preferably methacrylic acid or its salt, and (II) 5 to 60 mol% of structural units of a monomer having repeat units of formula (B1) in which R11, R12 and R13 independently of one another are selected from the group consisting of H, methyl and ethyl, R4 is H or an alkyl group having 1 to 4 carbon atoms, X is selected from the group consisting of O, COO, CONH, CH2O or CH2CH2O, Y is an ethylene group Z is a propylene group, a butylene group or a phenylethylene group, m is an integer from 0 to 100, n is an integer from 1 to 100, and m + n is greater than 5, and (C) at least one nonionic copolymer, which contains at least one structural unit having aromatic groups and at least one structural unit having polyethylene glycol groups, and (H) water.

2. Pigment preparation according to Claim 1, wherein the structural unit (I) of (B) is acrylic acid or methacrylic acid, or salts thereof, more preferably methacrylic acid or salts thereof.

3. Pigment preparation according to Claim 1 and / or 2, wherein the fraction of the structural units (I) is from 45 to 85 mol%.

4. Pigment preparation according to one or more of Claims 1 to 3, wherein the fraction of the structural units (II) is from 15 to 55 mol%.

5. Pigment preparation according to one or more of Claims 1 to 4, in which R11, R12 and R13 independently of one another are selected from the group consisting of H or methyl.

6. Pigment preparation according to one or more of Claims 1 to 5, wherein R12 is methyl and R11 and R13 are H.

7. Pigment preparation according to one or more of Claims 1 to 6, wherein is H or a methyl group.

8. Pigment preparation according to one or more of Claims 1 to 7, wherein X is O or C(O)O.

9. Pigment preparation according to one or more of Claims 1 to 8, wherein Z is propylene or phenylethylene.

10. Pigment preparation according to one or more of Claims 1 to 9, wherein m is an integer from 1 to 10, more preferably from 2 to 5, for example 3 or 4.

11. Pigment preparation according to one or more of Claims 1 to 10, wherein n is an integer from 5 to 45, more preferably 8 to 14.

12. Pigment preparation according to one or more of Claims 1 to 11, wherein (m+n) is an integer from 8 to 49.

13. Pigment preparation according to one or more of Claims 1 to 12, wherein the copolymer (C) comprises not only at least one structural unit having polyoxyethylene groups but also a structural unit having aromatic groups which derive from styrene oxide.

14. Pigment preparation according to one or more of Claims 1 to 12, wherein the copolymers (C) correspond to the formula (3), to the formula (4), or to mixtures thereof where n is an integer greater than or equal to 1, preferably equal to 1, R1 is an aliphatic, linear or branched hydrocarbon radical having 1 to 10 carbon atoms, a hydrogen atom, the structural unit -O-X, or the structural unit -CH2-OX, preferably a hydrogen atom, X corresponds to the formula (5) in which o is an integer from 1 to 50, preferably is an integer from 1 to 4, p is an integer from 1 to 200, preferably is an integer from 10 to 25, and (o+p) is greater than 2, preferably is an integer from 2 to 250.

15. Pigment preparation according to one or more of Claims 1 to 12, wherein the copolymers (C) correspond to the formula (6) in which q is an integer from 1 to 4, more preferably is an integer from 1 to 2, s is an integer from 5 to 50, more preferably is an integer from 5 to 20, R5 is H or an alkyl group having 1 to 4 carbon atoms, more preferably methyl, t is an integer from 0 to 10, more preferably is an integer from 1 to 4, u is an integer from 1 to 100, more preferably is an integer from 10 to 50, and t + u is greater than 10.

16. Pigment preparation according to one or more of Claims 1 to 15, comprising 5 to 80 wt% of component (A).

17. Pigment preparation according to one or more of Claims 1 to 16, comprising 1 to 20 wt% of component (B).

18. Pigment preparation according to one or more of Claims 1 to 17, comprising 1 to 20 wt% of component (C).

19. Use of a combination of polymers (B) and (C) as dispersant, wherein (B) is an anionic copolymer which contains (I) 40 to 95 mol% of structural units of an anionic monomer which is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, 2-carboxyethylacrylic acid, maleic acid, mixtures thereof and their respective salts, preferably methacrylic acid or its salt, and (II) 5 to 60 mol% of structural units of a monomer having repeat units of formula (B1) in which R11, R12 and R13 independently of one another are selected from the group consisting of H, methyl and ethyl, R4 is H or an alkyl group having 1 to 4 carbon atoms, X is selected from the group consisting of O, COO, CONH, CH2O or CH2CH2O, Y is an ethylene group Z is a propylene group, a butylene group or a phenylethylene group, m is an integer from 0 to 100, n is an integer from 1 to 100, and m + n is greater than 5, and (C) is a nonionic copolymer, which contains at least one structural unit having aromatic groups and at least one structural unit having polyethylene glycol groups, in the production of a pigment preparation comprising (A) at least one organic and / or inorganic pigment and / or filler, and (H) water.