MX2008009350A - Dispersing agent for aqueous pigment preparations - Google Patents

Abstract

The invention relates to aqueous pigment preparations containing (A) at least one organic and/or inorganic pigment as well as dispersing agent that comprises two or more structural units of formula (I) which are bound to a structural unit Y. In formula (I), a represents an integer from 1 to 100, b represents an integer from 0 to 100, c represents an integer from 1 to 100, units a, b, and c can be arranged statistically or in blocks, R2represents an aliphatic, linear or branched hydrocarbon radical with 1 to 30 carbon atoms, A represents hydrogen or an anionic radical of formulas -SO3M, -SO2M, -PO3M2, -CH2COOM, or (II), and M represents a hydrogen atom, a cation from the group comprising Na+, K+, NH4+, ethanolammonium, diethanolammonium, or triethanolammonium, or a secondary, tertiary, or quaternary ammonium ion that is substituted with alkyl groups, or a combination thereof. Structural unit Y represents a carbon-containing structural unit which can alkoxylate at least at two binding points that are formed by one or several nitrogen atoms, one or several oxygen atoms, or both.

Description

DISPERSANT AGENT FOR PREPARATIONS OF AQUEOUS PIGMENT DESCRIPTION OF THE INVENTION The present invention relates to dispersants for water-based pigment preparations and their use as colorants of macromolecular materials of all kinds, such as fiber materials, paper, and plastics, for example, and also as colorant of coating materials, paints, and inks, and additionally for printing two-dimensional structures such as sheets, paper, cardboard packaging, plastic, textiles, and leather, for example. The prior art has disclosed a variety of dispersants. DE-A-4 134 967 describes a block of type AB copolymers whose block A is formed by the polymerization of compounds containing vinyl groups and whose block B is a polyoxyalkylene block, obtainable by first subjecting the monomers containing vinyl groups to polymerization of free radicals at temperatures of 60 to 150 ° C in the presence of sufficient quantities of an initiator and of quantities, corresponding to the desired chain length, of a chain regulator which as well as the mercapto group also carries a functional group additional containing at least one active hydrogen radical, by reacting the resulting polymer, where the functional group having a The active hydrogen radical is an OH or COOH group, with an alkali metal hydroxide or alkali metal alkoxide, with removal of water or alcohol, respectively, and subjecting the modified polymer in accordance with an addition reaction with alkylene oxide, to temperatures from 20 to 180 ° C, until the desired molecular weight of block B is reached. EP-A-1 078 946 discloses copolymer polyalkylene oxides in blocks of the formula R10 (SO) a (EO) b (PO) c (BO) dR2 (I), wherein R1 is a cycloaliphatic or branched or chain radical linear having 8 to 13 carbon atoms, R 2 is hydrogen, an acyl radical, alkyl radical or carboxylic acid radical having in each case from 1 to 8 C atoms, SO is styrene oxide, EO is ethylene oxide, PO is propylene oxide, BO is butylene oxide, is already 1 to 1.9, b is 3 to 50, c is 0 to 3, and d is 0 to 3, with a, c or d being different than 0, and b being > = a + c + d. EP-A-0 940 406 discloses phosphoric esters (a) which are obtainable by reacting an oligo- or poly (alkyl) styrene? -hydroxy-functional with an alkylene oxide to give a copolymer of poly (alkyl) styrene- block (b) -polyalkylene oxide and the subsequent conversion in the corresponding phosphoric esters with a phosphorous compound that forms phosphoric esters, up to 100% of the terminal hydroxyl groups of these poly (alkyl) styrene-block (b) -oxide copolymers of polyalkylene being converted into phosphoric ester groups, and the phosphorous atoms being esterified singly and / or doubly depending on the chosen stoichiometric portions, or b) based on copolymers of polystyrene oxide-block (b) -polyalkylene oxide which are obtainable from a mono functional initiator alcohol by sequential addition of styrene oxide and alkylene oxide according to the desired sequence and length chain of the individual segments, and making them react in a subsequent manner to form the corresponding phosphoric esters, as described in a). It is an object of the present invention to provide new dispersants that allow the production of aqueous pigment preparations which meet the following requirements profile: the pigment preparations must possess a high shear stability and / or flocculation stability. The concentration of the pigments in the preparations should be as high as possible and should preferably be at least 20% by weight. The pigment preparations are to possess a high color strength and low viscosity and to have only a low tendency to foam. A storage stability of at least two years is the goal - in other words, the dispersed pigments should not agglomerate and settle within that time. Moreover, the dispersant should be free of alkylphenol derivatives and should not contain substantially volatile constituents. Surprisingly it has been found that, using copolymers of styrene oxide, alkylene oxides, and alcohols and amines with a functionality of two or more, it is possible to produce preparations of Aqueous pigments that meet the requirements described above. The aqueous pigment dispersions thus produced are resistant to shear, stable during storage, with little or no foam in their application, and have a low viscosity. The invention therefore provides the aqueous pigment preparations comprising (A) at least one organic and / or inorganic pigment, (B) at least one dispersant comprising 2 or more structural units of the formula I that are attached to a structural unit Y, where a is an integer from 1 to 100, b is an integer from 0 to 100, c is an integer from 1 to 100, and units a, b and c can be arranged randomly or by block, R2 is a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms, A is hydrogen or an anionic radical of the formulas -SO3M, S02M, -PO3M2, -CH2COOM or (I), and (II) M is a hydrogen atom, a cation of the group Na \ K \ NH4 +, ethanolammonium, diethanolammonium or triethanolammonium, or a secondary, tertiary or quaternary ammonium ion substituted with alkyl, or a combination of these, the structural unit Y being a structural unit containing carbon capable of alkoxylation in not less than two binding sites, and these linking sites are formed by one or more nitrogen atoms, one or more oxygen atoms, or both. The invention further provides the use of at least one dispersant (B) to disperse at least one organic and / or inorganic pigment in water. The invention further provides a method for dispersing at least one organic and / or inorganic pigment in water, by adding at least one dispersant (B) to the organic and / or inorganic pigment mixture and water. The structural unit Y is preferably derived from dihydric or polyhydric alcohols, monoamines or polyamines, or from amino alcohols, the latter containing at least one amino group and at least one OH group. These can be aromatic or aliphatic. These can be monomeric, oligomeric or polymeric. The number of OH groups they contain is preferably at least 2, more particularly 2 to 30, especially 3 to 15. "Derivatives" means that the structural unit Y occurs by the formal abstraction of hydrogen atoms from the alcohol and / or the amine groups. The structural unit Y is capable of alkoxylation in not less than two binding sites. This means that there are at least 2 sites in the structural unit Y in which the alkoxy groups of the formula I can be added. These binding sites are oxygen or nitrogen atoms. Due to the possible double alkoxylation of nitrogen atoms, it is sufficient for the structural unit Y to contain a nitrogen atom. Where, in any case, the structural unit does not contain a hydrogen atom, but if oxygen atoms are in place, then there are always at least two necessary oxygen atoms that are capable of alkoxylation, in order to be able to add to the oxygen atom. minus two alkoxy groups of the formula I. In another preferred embodiment the structural unit Y contains 1 to 100, more particularly 2 to 80, carbon atoms. a is preferably a number from 2 to 80, more particularly from 3 to 30, especially from 4 to 8. b is preferably a number from 1 to 80, more particularly from 2 to 30, especially from 3 to 8. c is preferably a number from 2 to 80, more particularly from 3 to 50, especially from 5 to 20.

The preference is given to a dispersant (B) in which a is a number from 1 to 40, b is zero, and c is a number from 5 to 50.

In a preferred embodiment, the dispersant (B) is of formula III -Y- (III) where Y is selected from the structural units of the formulas IV to XIV (IV) (V) (SAW) N 'I X (VII) (VI 11) X (X) (X) (XI) (XII) (XIH) (XIV) wherein RT is a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms, or a hydrogen atom, z is an integer greater than or equal to 1, n is an integer from 1 to 30, and X is an radical of formula I. n is preferably an integer from 1 to 4. z is preferably an integer from 1 to 30, more particularly a number from 2 to 20, especially 3.

Examples of compounds of which the structural unit Y is derived can be the following diols and polyols: monoethylene glycol, diethylene glycol, triethylene glycol, pentaethylene glycol, polyethylene glycols having a molecular weight of 200 to 12,000 g / mol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycols having a molecular weight of 200 to 6,000 g / mol, 1,4-butylene glycol, 1,3-butylene glycol, 1,2-butylene glycol, pentylene glycols, 1,6-hexyl glycol, cyclohexanediol, mixed polyglycols of ethylene glycol and propylene glycol or butylene glycols with molar ratios of ethylene glycol: propylene glycol or butylene glycol from 1: 100 to 100: 1, and also mixed polyglycols of ethylene glycol, propylene glycol, and butylene glycol , block polymers of ethylene glycol, propylene glycol, and butylene glycol with molecular weights of 500 to 12,000 g / mol more particularly block polymers of ethylene glycol with propylene glycol or butylene glycol in which the weight fraction of ethylene oxide in the block polymer is 10% to 90%, triols such as glycerol, trihydroxymethylpropane, polyols such as erythritol, pentaerythritol, sorbitol, diglycerol, polyglycerols, having 3 to 15 glycerol units, diols aromatics such as hydroxybenzyl alcohol, bisphenol A, pyrocatechol, resorcinol, and hydroquinone. Additional examples of compounds from which the structural unit Y is derived may be the following amines, diamines, polyamines, and hydroxyalkylamines: fatty acid amines having from 8 to 30 carbon atoms, such as octylamine, decylamine, cocaine, oleylamine, tallowamine, stearylamine, ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, polyethyleneimine, N-alkylpropylenediamine, N-alkylpropylenetriamine, N, N-bis-3-aminopropylamineamine, bis-N, N- (tallowalkylaminopropyl) ethylenediamine, methoxypolyethoxyamines, methoxypolyalkoxyamine (Jeffamines), ethanolamine, diethanolamine, triethanolamine, and 2-amino-2-methylpropanol (AMP). In addition to the constituents (A) and (B) the composition of the invention may comprise additional constituents. Thus in preferred embodiments the composition of the invention comprises. (C) if desired, one or more nonionic surfactants from the group of alkylphenol polyethylene glycol ethers, styrene-substituted polyethylene glycol ethers, alkylpolyethylene glycol ethers, polyethylene glycol fatty acid ethers, fatty acid polyglycosides, ethers of alkyl polyalkyl glycol of C8-C22 alcohols which have been reacted en bloc with ethylene oxide and propylene oxide, alkyl ethoxylates covered with C8-C22 alcohols which have been reacted with ethylene oxide and esterified with methyl chloride, butyl chloride or benzyl chloride, ethylene / propylene glycol block copolymers, and polyethylene glycol ethers and sorbitan ester; (D) if desired, one or more anionic surfactants from the group of sodium, potassium and ammonium salts of fatty acids, sodium alkylbenzenesulfonates, sodium alkylsulfonates, sodium olefin sulphonates, sodium polynaphthalenesulfonates, dialkyl ether ether disulfides of sodium Sodium, sodium, potassium, and ammonium alkyl sulphates, alkyl ether sulphylene glycol sodium, potassium, and ammonium sulphates, alkylphenol ether sulphates, polyethylene glycol sodium, potassium, and ammonium, mono- and dialkylsulfosuccinates sodium, potassium, and ammonium , and monoalkyl polyoxyethylsulfosuccinates, and alkyl polyethylene glycol phosphorus monoesters, diesters and tristers and mixtures thereof, phosphoric monoesters-ether of alchelfenol polyethylene glycol, diesters and triesters, and mixtures thereof, and also their sodium, potassium salts, and ammonium, carboxylic acids of alkyl polyethylene glycol ether and its sodium, potassium, and ammonium salts, sulfuric monoesters and phosphoric esters of substituted phenol styrene-ethoxylates, styrene-carboxylic acids of phenol substituted polyethylene glycol and its sodium, potassium salts , and ammonium, isotionates of sodium fatty acids, methyl taurides of sodium fatty acids, and fatty acid sarcosides of so it gave; (E) if desired, one or more polyethylene glycol ethers having an average molar mass between 200 and 2,000 g / mol; (F) if desired, one or more polyethylene glycol monoalkyl ethers having an average molar mass between 200 and 2,000 g / mol and an alkyl radical of 1-6 carbon atoms; (G) if desired, one or more organic solvents or one or more hydrotropic substances; (H) if desired, additional additives typical of aqueous pigment preparations; (J) If desired, one or more conservatives; Y (K) water The constituents (A) to (K) are present independently of one another preferably in the following amounts: (A) 3% to 80%, preferably 20% to 70%, more particularly 30% to 50% by weight of at least one organic and / or inorganic pigment. (B) 0 1% to 30%, preferably 1% to 15%, by weight of at least one dispersant (B). (C) 0% to 30%, preferably 1% to 15%, by weight of a nonionic surfactant. (D) 0% to 30%, preferably 1% to 15%, by weight of an anionic surfactant (E) 0% to 50%, preferably 1% to 20%, by weight of a polyethylene glycol ether having a average molar mass between 200 and 2,000 g / mol. (F) 0% to 50%, preferably 1% to 20%, by weight of a monoalkyl ether of polyethylene ghcol having an average molar mass between 200 and 2,000 g / mol and an alkyl radical of 1-6 carbon atoms. (G) 0% to 30%, preferably 0% to 20%, by weight of an organic solvent or a hydrotropic substance (H) 0% to 10%, preferably 0% to 5%, by weight of additional additives typical for preparations of aqueous pigment. (J) 0% to 2%, preferably 0 02% to 0.05%, by weight of a preservative (K) 5% to 90%, preferably 10% to 70%, by weight of water.

The percentages by weight are based in each case on the total weight of the pigment preparation. Where one or more of the components (C), (D), (E), (F), (G), (H), and (J) are present, their minimum concentration independently of one another is judiciously at least 0.01%, preferably at least 0.1%, by weight, based on the total weight of the pigment preparation. The component (A) of the pigment preparation is a finely divided organic or inorganic pigment or a mixture of different organic and / or inorganic pigments. These pigments can be used in the form of a dry powder, in the form of granules, or also in the form of wet cake-water. Suitable organic pigments include monoazo, disazo, azo laquedo, β-naphthol, naphthol AS, benzimidazolone, disazo condensation, and azo-metal complex pigments and polycyclic pigments such as, for example, phthaanine, quinacridone, perylene, perinone, thioindigo, antantrone, anthraquinone, flavantrone, ndantrone, isoviolantrone, pyrantrone, dioxazine, quinophthalone, isoindolinone, isoindoline, and diketopyrrolo-pyrrole pigments or carbon blacks. As an exemplary selection of particularly preferred organic pigments mention may be made of carbon black pigments, such as gas blacks or furnace blacks; monoazo and disazo pigments, more particularly pigments of the Pigment Color Index 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; ß-naphthol and naphthol AS pigments, more particularly the pigments of the Color 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 o Pigment Coffee 1; lacquered azo pigments and pigments of metal complexes, more particularly the pigments of the Red Pigment Color Index 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, more particularly the pigments of the Color Pigment Yellow 120 index, 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, more particularly the pigments of Color Pigment Yellow Index 139, Pigment Yellow 173; phthalocyanine pigments, more particularly the pigments of the Color 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; antantrone, anthraquinone, quinacridone, dioxazine, indantrone, perylene, perinone and thioindigo pigments, more particularly the pigments of the Color Pigment Yellow Index 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, more particularly the pigments of the Color Pigment Red 169, Pigment Blue 56 or Pigment Blue 61; diketopyrrolopyrrole pigments, more particularly the pigments of the Pigment Red Color Index 254, Pigment Red 255, Pigment Red 264, Pigment Red 270, Pigment Red 272, Pigment Orange 71, Pigment Orange 73, Pigment Orange 81. The organic pigment is preferably combined with carbon black and / or titanium dioxide.

Also suitable are lacquered inks such as Ca, Mg, Al lacquers of inks containing sulfonic and / or carboxylic acid groups. Examples of suitable inorganic pigments include titanium dioxides, zinc sulphides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, titanium manganese solvents, oxides of cobalt, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, cobalt spinel with nickel and zinc, synthetic rubies based on iron and chromium with copper, zinc, and manganese, bismuth vanadates and also pigments supplementary More particularly use is made of the pigments of Color Pigment Yellow Index 184, Pigment Yellow 53, Pigment Yellow 42, Pigment Yellow Coffee 24, Pigment Red 101, Pigment Blue 28, Pigment Blue 36, Pigment Green 50, Pigment Green 17, Pigment Black 11, Black Pigment 33 and White Pigment 6. Preference is also given to frequently using mixtures of inorganic pigments. Mixtures of organic and inorganic pigments are likewise frequently used. Instead of pigment dispersions it is also possible to produce dispersions comprising as solids, for example, finely divided minerals, minerals, poorly soluble or insoluble salts, particulate waxes or plastics, inks, pesticides and crop protection agents, biocides, herbicides, insecticides, fungicides, UV absorbers, optical brighteners or polymerization stabilizers. Component (B) is typically used as an aqueous solution to produce the pigment preparations of the invention. Component (B) is prepared by addition and anionic polymerization of styrene oxide, ethylene oxide, propylene oxide, butylene oxide or long chain alkylene oxides with compounds comprising at least two heteroatoms selected from oxygen or nitrogen, examples they are difunctional or polyfunctional alcohols or amines or amino alcohols. The alkoxylation takes place in one or more of the oxygen or nitrogen atoms of this compound, but at least in two places in the molecule. These sites are alkoxylable oxygen and / or nitrogen atoms, preferably alcohol and / or amino groups. The compound which is alkoxylated then forms the structural unit Y. The anionic polymerization can take place randomly or block. Following the copolymerization, the nonionic dispersant (B) formed in a first stage can be modified by the addition of an anionic group. Suitable anionic groups are sulfuric monoesters such as, which are obtainable by reacting the nonionic dispersants of the invention with amidosulfonic acid, or phosphoric esters, which can be prepared by reacting the nonionic dispersants of the invention with orthophosphoric acid, polyphosphoric acid or phosphorous pentoxide P205. It is further possible to prepare sulfosuccinic monoesters by reacting the nonionic dispersants of the invention with anhydride maleic and sodium sulfite or sodium bisulfite, and carrying out the neutralization with an aqueous solution of sodium hydroxide. Ethercarboxylic acids can be prepared by reacting the nonionic dispersants of the invention with monochloroacetic acid under alkaline conditions. The component corresponding to component (G) are hydrotropic or organic substances soluble in water. Compounds of this type, which where appropriate also serve as solvents, or are oligomeric or polymeric in nature, examples being formamide, urea, tetramethylurea, e-caprolactam, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, a-methyl-α-hydroxy-polyethylene glycol esters, dimethyl polyethylene glycol esters, dipropylene glycol, polypropylene glycol, dimethyl polypropylene glycol esters, copolymers of ethylene glycol and propylene glycol, butyl glycol, methyl cellulose, glycerol, diglycerol, polyglycerol, N-methyl-pyrrolidone , 1,3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzenesulfonate, sodium xylene sulphonate, sodium toluenesulfonate, sodium cumenesulfonate, sodium dodecylsulfonate, sodium benzoate, sodium salicylate, sodium butyl monoglycol sulfate, cellulose derivatives , derivatives of gelatin, polyvinylpyrrolidone, polyvinyl alcohol, polyvinylimidazole, and copolymers and terpolymers of vinylpyrrolidone, ace vinyl acetate, and vinylimidazole, polymers containing vinyl acetate units are subsequently capable of being subjected to hydrolysis to form vinyl alcohol.

As typical additives (Component H) it is conveniently possessed by additional cationic, anionic, amphoteric or non-ionic surfactants and substances that promote pigment moisture (wetting agents), as well as anti-settling agents, light stabilizers, antioxidants, degassing / anti foamers, suds suppressors, fillers, grinding assistants, viscosity stabilizers and additives that benefit the rheology. Suitable agents for regulating viscosity include, for example, polyvinyl alcohol and cellulose derivatives. Water-soluble natural or synthetic resins and also polymers such as film formers or binders for increasing adhesive strength and abrasion resistance are also suitable. The pH regulators include bases and organic or inorganic acids. Preferred organic bases are amines, such as ethanolamine, diethanolamine, triethanolamine, N, N-dimethylethanolamine, diisopropylamine, aminomethylpropanol or dimethylaminomethylpropanol, for example. Preferred inorganic bases are lithium, potassium and sodium hydroxide or ammonia. The water used to produce the pigment preparations, component (K), is preferably used in the form of distilled or deionized water. Water to drink also (water from the supply network) and / or water of natural origin can be used. In one embodiment of the invention the pigment preparation of the invention contains the constituents (A) and (B) and also water at 100% by weight.

The pigment preparations possess good storage stability and exhibit a very low tendency towards agglomeration and toward sedimentation. Pigment preparations possess high color strengths, defined colors, and low viscosities. The present invention also provides a process for producing the preparations of pigment of the present invention, which comprises dispersing the component (A) in the form of powder, granules or aqueous paste in the presence of water (K) and also of components (B) and where appropriate (C), ( D), (E), (F), (G), (H), and (J), in a conventional manner, then mix in, where appropriate, water (K), and adjust the resulting aqueous pigment dispersion at the desired concentration with water Preferably the components (B), (C), (D), (E), (F), (G), (H), (J), and (K) are mixed and homogenized, and then component (A) is stirred in the initial mixture, with the pigment being added and pre-dispersed. Depending on the hardness of the grain of the pigments used, this is followed by fine division or fine dispersion, with the help of a dispersion or grinding assembly, with cooling where appropriate Agitator mechanisms , dissolvers (sawtooth agitators), broken stators mills, ball mills, agitator ball mills such as sand mills, and grain mills, high speed mixers, kneading apparatus, roll mills or grain mills High performance can be used for this purpose The pigments are finely dispersed or ground until the desired particle size distribution is reached, in operations that can take place at temperatures in the range from 0 to 100 ° C, advantageously at a temperature between 10 and 70 ° C, preferably at 20 to 60 ° C. Following the fine dispersion the pigment preparation can be further diluted with water, preferably distilled or deionized water. The pigment preparations produced with the dispersants of the invention are suitable for pigmenting and coloring macromolecular materials of all types, such as natural and synthetic material fibers, preferably cellulose fibers, more particularly for coloring textiles and printing textiles. The dispersants of the invention are free from alkylphenol and alkylphenol ethoxylates and according to German appendix 38 of the provisions for waste water management for wasted water in textiles, as long as the dispersants do not reduce the surface tension of the water below 45. mN / m in a 0.5% solution. By controlling the degree of alkoxylation, in other words by adding a sufficient amount of styrene oxide, ethylene oxide or other alkylene oxides, the surface tension of the solution strength at 0.5% can be maintained above the limit of 45 mN / m. Accordingly, the dispersants of the invention are particularly suitable for use in textile finishes, such as dyeing polyester fibers and other synthetic fibers and printing textiles such as cotton or blends of polyester / cotton fabric in a printing process. of pigment, for example.

The pigment preparations are additionally suitable for pigmenting and / or producing colored coatings and emulsion paints, dispersion lacquers, printing inks, such as gravure printing inks, decorative inks, flexographic or textile inks, wallpaper colors , water-dilutable paints, wood preservation systems, systems for coloring fabrics for viscose, nail varnishes, sausage skin, seeds, fertilizers, glass bottles, and also for coloring the paper mass and coloring laminates, roof tiles , for coloring plastering layers, wood stains, colored pencil sprigs, fiber tip pens, waxes, paraffins, graphics inks, ballpoint pens, chalk, laundry detergents and cleaning products, shoe waxes, products of latex, abrasives, and also to color plastics and high molecular weight materials. Examples of organic materials of high molecular mass are cellulose ethers and cellulose esters, such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as addition polymerization resins or condensation resins, are examples amino resins, more particularly formaldehyde-melamine and urea-resins, alkyl resins, acrylic resins, phenolic resins, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic esters, polyamides, polyurethanes or polyesters , rubber, casein, latex, silicone, silicone resins, individually or in a mixture.

The pigment preparations produced with the dispersants in the invention are further suitable for producing printing inks for use in all conventional ink jet printers, more particularly those based on the piezo process or bubble injection. These printing inks can be used to print paper, and also synthetic or natural fiber materials, sheets and plastics. Additionally the pigment preparations can be used to print any of a very wide variety of types of substrate materials uncoated or coated: for example, for printing paperboard, paperboard, wood and wood-based materials, metallic materials, semiconductor materials, Ceramic materials, glass, fiberglass and ceramic fibers, inorganic building materials, concrete, tanned leather, edibles, cosmetics, skin and hair. The substrate material may be two-dimensionally planar or spatially extended, i. e., in three-dimensional form, and may have been coated or printed completely or only in parts. Additional suitable applications of the dispersants of the invention are pigment preparations which are used as dyes in toners and electro photographic developers, such as one or two component powder toners (also called one or two component developers), magnetic toners, liquid toners, latex toners, polymerization toners, special toners, for example. Typical toner binders in this context are resins from addition polymerization, polyaddition resins, and polycondensation resins, such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, and epoxyphenolic resins, polysulfones, polyurethanes, individually or in combination, and also polyethylene and polypropylene, which can contain additional ingredients, such as charge control agents, waxes or flow assistants, or may be subsequently modified with these adjuvants. A possible further application of the dispersants of the invention is the production of pigment preparations which are useful as colorants in powders and powder coated materials, more particularly in triboelectrically or electrokinetically atomizable powder coated materials which are used to coat the surface of articles made, for example, of metal, wood, plastic, glass, ceramics, concrete, textile, paper or rubber. The powder coated resins used herein are typically epoxy resins, carboxyl- and hydroxyl- containing polyester resins. The resin combinations also find use. For example, epoxy resins are frequently used in combination with carboxyl- and hydroxyl- containing polyester resins. Typical hardening components (depending on the resin system) are, for example, acid anhydrides, midazoles, and also dicyandiamide and derivatives thereof, clogged isocyanates, bisacyl urethanes, phenolic resins and melamine resins, triglycidyl isocyanurates, oxazolines, and acids dicarboxylic.

The polymeric dispersants of the invention are further suitable for producing pigment preparations which are used as dyes in aqueous or non-aqueous inks, preferably inkjet inks, microemulsion inks, UV curable inks and in those inks that operate in accordance with the invention. to the hot melt technique. The pigment preparations of the invention are also suitable, additionally, as colorants for color filters for flat screens, both for the generation of additive and subtractive color, and additionally for photoresistors, and also as dyes for electronic inks (or "e-inks"). ") or electronic paper (or" e-paper ").

EXAMPLES Examples of the dispersants of the invention are the following compounds. As a starter molecule, diamines or diamines were introduced as an initial charge, and the desired amount of styrene oxide and ethylene oxide was added in such a way that the alkoxylation was carried out in blocks.

Production of a pigment preparation The pigment, in the alternative form of a powder, granules or paste, was added in deionized water together with the dispersants and the other adjuvants and then homogenized and pre-dispersed using a dissolver (eg VMA-Getzmann). GmbH, model CN-F2) or other suitable device. The subsequent fine dispersion took place with a grain mill (eg, APS 500 from VMA-Getzmann) or also from another dispersion assembly The grinding was carried out with silicuartzite or zirconium grains mixed with oxide grains with a size d = 1 mm, with cooling until the desired color strength and colouristic properties were obtained. Subsequently, the dispersion was adjusted with deionized water to the desired concentration of the final pigment, the grinding media was separated, and the pigment preparation was isolated. The pigment preparations described in the following examples were produced by the method described above, the following constituents being used in the stated amounts to give 100 parts of the respective pigment preparation. In the following examples, the parts are by weight.

EXAMPLE 1 parts CI Pigment Black 7 (® Special black 4, Degussa AG, component A) 4 parts Species 1 dispersant (component B) 2 parts alkylpolyalkylene glycol ester (component C) 9.5 parts polyethylene glycol, molecular weight 200 g / mol (component E ) 0.5 parts defoaming (component H) 0.2 parts preservative (component J) 58.8 parts demineralized water (component K) Components (B), (C), (E), (H), and (J) were loaded into a polishing container and mixed. Subsequently, the pulverulent component (A) was added and predispersed using the solvent. A fine dispersion was carried out in a grain mill with zirconium oxide grains of size d = 1 mm with cooling. Subsequently, the polishing media was separated and the pigment preparation was isolated. The pigment preparation was stored at 60 ° C for one week and inspected. The viscosity of the pigment preparation was measured using a Brookfield digital viscometer model DV-II at 100 revolutions per minute and axis 4. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and foam-free . The viscosity of the pigment preparation was 15 mPass.

EXAMPLE 2 parts CI Pigment Violet 19 (® Red Hostaperm E5B 02, Clariant GmbH, component A) 4 parts Species 2 dispersant (component B) 2 parts alkylpolyalkylene glycol ester (component C) 9.5 parts polyethylene glycol, molecular weight 200 g / mol (component E) 0.5 parts defoaming (component H) 0. 2 parts preservative (component J) 63.8 parts demineralized water (component K) For the production and testing of the pigment preparation the process specified in Example 1 was repeated. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and free of foam. The viscosity of the pigment preparation was 10 mPa s.

EXAMPLE 3 40 parts CI Pigment Red 146 (® Permanent Carbide FBB02, Clariant GmbH, component A) 4 parts Species 3 dispersant (component B) 2 parts alkylpolyalkylene glycol ester (component C) 9.5 parts polyethylene glycol, molecular weight 200 g / mol (component E ) 0.5 parts defoamer (component H) 0.2 parts preservative (component J) 43.8 parts demineralized water (component K) For the production and testing of the pigment preparation the process specified in Example 1 was repeated. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and free of foam. The viscosity of the pigment preparation was 53 mPa s.

EXAMPLE 4 40 parts CI Pigment Yellow 83 (® Yellow HR02, Clariant GmbH, component A) 8 parts Species 1 dispersant (component B) 2 parts alkylpolyalkylene glycol ester (component C) 9.5 parts polyethylene glycol, molecular weight 200 g / mol (component E) 0.5 parts defoamer (component H) 0.2 parts preservative (component J) 39.8 parts demineralized water (component K) For the production and testing of the pigment preparation the process specified in Example 1 was repeated. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and free of foam. The viscosity of the pigment preparation was 210 mPa s.

EXAMPLE S 40 parts C. I. Pigment Red 146 (® Permanent Carbide FBB02, Clariant GmbH, component A) 4 parts Species 5 dispersant (component B) 2 parts ester alkylpolyalkylene glycol (component C) 9. 5 parts polyethylene glycol, molecular weight 200 g / mol (component E) 0.5 parts defoamer (component H) 0.2 parts preservative (component J) 43.8 parts demineralized water (component K) For the production and testing of pigment preparation the process specified in Example 1 was repeated. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and free of foam. The viscosity of the pigment preparation was 80 mPa s.

EXAMPLE 6 60 parts CI Pigment Red 102 (® Red Bayferrox 130, Lanxess AG, component A) 9 parts Species 6 dispersant (component B) 1 part alkylpolyalkylene glycol ester (component C) 0.5 parts defoamer (component H) 0.2 parts preservative (component J ) 29.3 parts demineralised water (component K) For the production and testing of the pigment preparation the process specified in Example 1 was repeated. After one week of storage at 60 ° C the pigment preparation was liquid, homogeneous, and foam-free but slightly thixotropic The viscosity of the pigment preparation was 620 mPa s EXAMPLE 7 parts CI Pigment Blue 15 3 (® Blue Hostaperm B2G, Clapant GmbH, component A) 15 parts Species 4 dispersant (component B) 1 part alkylpolyalkylene ghcol ester (component C) 20 parts propylene ghcol (component G) 0 2 parts conservative ( component J) 33 8 parts demineralized water (component K) The pigment preparation was produced in the same manner as in Example 1 The pigment preparation was stored at 50 ° C for 4 weeks and was inspected The viscosity was determined using a viscometer cone / Haake plate (Roto Visco 1) at 20 ° C (titanium cone 0 60 mm, 1 o), the viscosity being investigated as a function of the shear rate in a range between 0 and 200 s 1 The viscosities were measured in the shear rate of 60 s 1 The pigment preparation had a great color strength and did not foam After storage at 50 ° C for four weeks, the pigment preparation was liquid and homogeneous The viscosity of the preparation Pigment ration was 500 mPa s EXAMPLE 8 parts CI Pigment Blue 15: 3 (® Blue Hostaperm B2G, Clariant GmbH, component A) 15 parts Species 3 dispersant (component B) 1 part alkylpolyalkylene glycol ester (component C) 20 parts propylene glycol (component G) 50.2 parts conservative ( component J) 29.8 parts demineralized water (component K) For the production and testing of the pigment preparation the process specified in Example 7 was repeated. The pigment preparation had a great color strength and did not foam. After storage at 50 ° C for four weeks, the pigment preparation was liquid and homogeneous. The viscosity of the pigment preparation was 420 mPa s.

EXAMPLE 9 parts CI Pigment Blue 15: 3 (® Blue Hostaperm B2G, Clariant GmbH, component A) 15 parts Species 5 dispersant (component B) 20 parts propylene glycol (component G) 5 parts surfactant agent (component H) 0.2 parts preservative ( component J) 29. 8 parts demineralized water (component K) For the production and testing of the pigment preparation the process outlined in Example 7 was repeated. The pigment preparation had a great color strength and did not foam. After storage at 50 ° C for four weeks, the pigment preparation was liquid and homogeneous. The viscosity of the pigment preparation was 540 mPa s.

Claims (18)

NOVELTY OF THE INVENTION CLAIMS

1. - An aqueous pigment preparation comprising (A) at least one organic and / or inorganic pigment, (B) at least one dispersant comprising 2 or more structural units of the formula I that are attached to a structural unit Y, where a is an integer from 1 to 100, b is an integer from 0 to 100, c is an integer from 1 to 100, and units a, b and c can be arranged randomly or by block, R2 is a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms, A is hydrogen or an anionic radical of the formulas -S03M, -S02M, -P03M2, -CH2COOM or (I), and 00

M is a hydrogen atom, a cation of the group Na +, K +, NH 4 +, ethanolammonium, diethanolammonium or triethanolammonium, or a secondary, tertiary or quaternary ammonium ion substituted with alkyl, or a combination of these, the structural unit Y being a structural unit containing carbon capable of alkoxylation at not less than two binding sites, and these linking sites are formed by one or more nitrogen atoms, one or more oxygen atoms, or both. 2. The composition according to claim 1, further characterized in that the structural unit Y is selected from dihydric or polyhydric alcohols, amines having at least one amino group, or amino alcohols containing at least one amino group and at least one an OH group.

3. The composition according to claim 2, further characterized in that the structural unit Y is derived from a compound containing 2 to 30 amino groups, OH groups or both.

4. The composition according to one or more of claims 1 to 3, further characterized in that the dispersant (B) is of formula III ? - (li!) where Y is selected from the structural units of formulas IV to XIV (IV) (V) (SAW) N 'I X (VII) (V1H) (IX) 10 (X) 20 R, (XI) (XII) (XIV) wherein Ri is a linear or branched aliphatic hydrocarbon radical having 1 to 30 carbon atoms, or a hydrogen atom, z is an integer greater than or equal to 1, n is an integer from 1 to 30, and X is an radical of formula I.

5. The composition according to one or more of claims 1 to 4, further characterized in that a is a number from 1 to 10, b is zero and c is a number from 5 to 30.

6. - The composition according to claims 4 and / or 5, further characterized in that n is an integer from 2 to 4.

7. The composition according to one or more of claims 1 to 6, further characterized in that M is sodium, potassium, ammonium, ethanolammonium, triethanolammonium or trimethylammonium.

8. The composition according to one or more of claims 1 to 7, further characterized in that it contains 3% to 80% by weight of at least one organic and / or inorganic pigment.

9. The composition according to one or more of claims 1 to 8, further characterized in that it contains 0.1% to 30% by weight of at least one dispersant (B).

10. The composition according to one or more of claims 1 to 9, further characterized in that it contains up to 30% by weight of a nonionic surfactant.

11. The composition according to one or more of claims 1 to 10, further characterized in that it contains up to 30% by weight of an anionic surfactant.

12. The composition according to one or more of claims 1 to 11, further characterized in that it contains up to 50% by weight of a polyethylene glycol ether having an average molar mass between 200 and 2,000 g / mol.

13. The composition according to one or more of claims 1 to 12, further characterized in that it contains up to 50% by weight of a monoalkyl polyethylene glycol ether having a molar mass average between 200 and 2,000 g / mol and an alkyl radical of 1 to 6 carbon atoms.

14. The composition according to one or more of claims 1 to 13, further characterized in that it contains 0% to 30% by weight of an organic solvent or a hydrotropic substance.

15. The composition according to one or more of claims 1 to 14, further characterized in that it contains up to 10% by weight of other additives typical of aqueous pigment preparations.

16. The composition according to one or more of claims 1 to 15, further characterized in that it contains up to 2% by weight of a preservative.

17. The use of at least one dispersant (B) as claimed in claim 1, for dispersion of at least one organic and / or inorganic pigment in water.

18. A method for dispersing at least one organic and / or inorganic pigment in water, adding at least one dispersant (B) as claimed in claim 1 to the mixture of organic and / or inorganic pigment and water.