EP2802632A1

EP2802632A1 - Inorganic pigment dispersions containing fatty acid ethanol amide ethoxylates and amines

Info

Publication number: EP2802632A1
Application number: EP12809124.6A
Authority: EP
Inventors: Hendrik Ahrens
Original assignee: Clariant Finance BVI Ltd
Current assignee: Clariant International Ltd
Priority date: 2012-01-13
Filing date: 2012-12-19
Publication date: 2014-11-19
Also published as: WO2013104406A1; US8968462B2; US20150000566A1

Abstract

The subject matter of the invention relates to aqueous pigment preparations containing (A) 30 to 75% by weight of at least one inorganic white or colored pigment or a mixture of different inorganic white or colored pigments, (B) 0.01 to 15% by weight of at least one fatty acid ethanol amide ethoxylate of the formula (I), in which R¹ is a linear or branched alkyl radical or alkenyl radical with 7 to 21 carbon atoms, and n is a whole number from 2 to 40, (C) 0.01 to 5% by weight of at least one amine of the formula (II), in which R² is a linear or branched alkyl radical or alkenyl radical with 8 to 22 carbon atoms, identical to or different from R¹, A represents an iminopropyl group -NH-CH₂-CH₂-CH₂-, an oxyethyl group -O-CH₂-CH₂- or an oxypropyl group -O-CH₂-CH (CH₃)-CH₂-, and a is a whole number from 0 to 5, wherein the compound of the formula (II) can be present in the form of an ammonium salt, and (E) water.

Description

Fatty acid ethanolamide ethoxylates and amines containing inorganic

pigment dispersions

The present invention relates to aqueous pigment dispersions containing Fettsäureethanolamidethoxylate and amines as surface modifiers and dispersants, and their use for dyeing macromolecular materials of all kinds, such as fiber materials, pulp, pulp, paints, and their use for printing two-dimensional fabrics such as Paper, cardboard, plastic, textiles and leather.

For the coloring of macromolecular materials, in particular of paints and varnishes, aqueous pigment preparations with organic or inorganic pigments are produced.

Depending on the desired color strength of the pigment preparations, pigments in a concentration range from 1 to 75% by weight are used for the preparation of aqueous pigment preparations with inorganic pigments.

In addition, these aqueous pigment preparations usually contain wetting and dispersing agents and water and also auxiliaries customary for pigment preparations, such as, for example, additional solvents, humectants, preservatives, defoamers, pH regulators and rheology additives which serve as anti-settling agents. The wetting and dispersing agents for inorganic pigments have the task of wetting the pigments, dispersing them and stabilizing the pigment preparations.

According to the prior art, polymeric dispersants and anionic, cationic and nonionic surfactants are used to disperse and inorganic pigments in aqueous dispersions or to modify the surface of the organic and inorganic pigments. As polymeric dispersants are usually low molecular weight

Polymers of acrylic acid or copolymers of acrylic acid, methacrylic acid and maleic acid and their sodium, potassium or ammonium salts used. The anionic surfactants used are amphiphilic compounds whose hydrophobic group is an aliphatic or aromatic radical and whose hydrophilic group contains a carboxylic, sulfonic or phosphonic acid group or represents an ester of sulfuric acid or phosphoric acid. As nonionic surfactants, which are used as dispersants for pigment preparations, fatty alcohol ethoxylates, Alkylphenolethoxylate and copolymers of ethylene oxide, propylene oxide and styrene oxide are described.

Cationic surfactants used as dispersants for pigment preparations are amines, their ammonium salts, amine oxides, betaines or quaternaries

In particular, long-chain aliphatic alkylamines and alkyldiamines are described for a large number of applications in which the dispersibility of inorganic pigments in plastics, in aqueous and solventborne coating materials or in the processing of paper, cardboard, plastic, textiles and leather is improved.

The following is an overview of the state of the art

used dispersing agent. DE-10341724 describes alkali-resistant alkoxylates as dispersants for coatings and color formulations.

DE-19743841 describes mixtures of polyphosphates and polyacrylates in the form of their alkali metal or ammonium salts as dispersants for inorganic pigments and fillers in emulsion paints.

EP-1167452 describes the use of block copolymers

Phosphoric acid esters and their salts as pigment wetting agents for pigment pastes, aqueous, solvent-based, low-solvent and solvent-free lacquers and

Printing inks. The block copolymers of phosphoric acid esters are prepared by blockwise reaction of alkylol with styrene oxide, ethylene oxide and optionally with further alkylene oxides and then reacted to form the phosphoric acid ester.

EP-1771520 describes alcohol alkoxylates as low-foaming wetting agents for coating materials of binders, pigments, fillers, additives and solvents.

EP-2193152 describes anionic dispersants from the group of

Fatty acids and their salts, sodium alkylbenzenesulfonates, sodium alkylsulfonates, sodium olefinsulfonates, sodium polynaphthalenesulfonates, alkyl sulfates,

Alkylpolyethylenglykolethersulfate, Alkylphenolpolyethylenglykolethersulfate, Sulfobernsteinsäureester and Alkylpolyethylenglykoletherphosphorsäureester.

GB-79 767 describes polymers and copolymers of acrylic acid and

Methacrylic acid and its esters and salts as dispersants for inorganic pigments.

GB-1080115 describes the use of long-chain alkylamines having 8 to 20 carbon atoms, their salts and ethoxylates as

Surface modifier in the synthesis of organic pigments. US 2192956 describes the use of amines and quaternaries

Ammonium compounds as dispersants for organic pigments.

US-3015573 and US-3172772 describe the use of low molecular weight ammonium salts as surface modifiers for titanium dioxide pigments.

US-3775148 describes aliphatic amines, amine salts and amine oxides having from 1 to 20 carbon atoms as surface modifiers for diarylide pigments. US Pat. No. 3,945,964 describes alcohol alkoxylates as dispersants for aqueous epoxy resin dispersions.

US 4091164 describes ethylene oxide / propylene oxide block copolymers as

Dispersants for inorganic pigments and fillers in thermoplastics.

US-4127420 describes alkyl-containing amines and alkoxylates as

Dispersant for organic pigments.

US-4156616 describes the use of long-chain aliphatic

Amine ethoxylates for aqueous dispersions with organic and inorganic pigments. US-4439238 describes aliphatic and alicyclic amines and diamines of 1 to 22 carbon atoms for phthalocyanine pigments.

US-4563221 describes the use of fatty amines as dispersants for inorganic pigments in plastics.

US 4599114 describes the use of fatty alkylpropylenediamines for the surface treatment of titanium dioxide and other inorganic pigments for dispersion in coating materials, plastics and papermaking. US-5382288 describes the use of amides, diamines and long-chain primary and secondary alkylamines for the modification of organic azo pigments.

US-6231662 describes the use of reaction products

low molecular weight amines and fatty amines with dicarboxylic acids as

Surface modifier for organic and inorganic pigments.

US-6287348 describes the reaction of C12-C24 alkylamines and C12-C24 Alkyl monoether amines with reactive dyes for the preparation of colorants for hydrocarbons and waxes.

US-6312514 describes diol alkoxylates as dispersants for aqueous

Pigment concentrates.

No. 6348092 describes the use of diamines and alkyletheramines as dispersants for titanium dioxide in mineral oil-containing alkyd paints. US 6379443 describes alkyl alkoxylates as dispersants for ink jet inks.

US-6471764 describes polyalkylene glycol ether amines as dispersing additives for organic pigments. US-6488759 describes alkylpolypropyleneamines as dispersants and

Surface modifier for organic monoarylide pigments.

US Pat. No. 5,582,505 describes branched alcohol alkoxylates as dispersants for aqueous pigment dispersions.

US-7008475 describes naphthol alkoxylates as dispersants for organic pigments.

US-2003/101910 describes carboxymethylated and phosphated

Polystyrene phenol alkoxylates as dispersants for carbon black dispersions.

US-2004/040471 describes reaction products of fatty amines as auxiliaries for the preparation of aqueous pigment preparations. US-2007/125260 describes the use of primary and secondary fatty amines as dispersants for azo pigments. US-2008/1 10368 describes a paint formulation of a pigment powder and nonionic surfactants selected from the group of acetylene surfactants, alkylphenol ethoxylates, ethylene oxide / propylene oxide block copolymers,

Alcohol ethoxylates and mixtures thereof.

Although a large number of compounds are proposed as suitable wetting and dispersing agents in the prior art, in practice there has been a lack of effective dispersants for pigment dispersions which meet the requirements for sedimentation stability, rheological behavior,

Color yield of the pigments and to a low human and ecotoxicological behavior sufficient.

In addition, Environmental Labeling Directives restrict the use of known wetting and dispersing aids so that those skilled in the art are always on the look-out for new dispersants and combinations to prepare liquid, stable, aqueous pigment preparations. It is desirable to prepare aqueous pigment preparations which are not subject to labeling according to the European regulation 2008-1272 EC. It is an object of the present invention to produce stable and flowable aqueous pigment preparations which are not subject to labeling according to the European regulation 2008-1272 EC and which show no sedimentation of the pigments used over a longer period of time and with which aqueous and solventborne paints, Dye varnishes and glazes alike. When tinting aqueous paints and

Inks, in particular emulsion paints, silicate disperison paints and aqueous silicone resin paints, the pigment preparations according to the invention should show no rubout problems. Surprisingly, it has been found that pigment preparations that

Fatty acid ethanoiamide ethoxylates of the formula I in combination with amines of the formula II, fulfill this task. The invention therefore relates to aqueous pigment preparations containing

(A) 30 to 75 wt .-% of at least one inorganic white or

Colored pigment or a mixture of different inorganic white or colored pigments,

(B) 0.01 to 15% by weight of at least one fatty acid ethanolamide ethoxylate of the formula (I),

wherein

R ^{1 is} a linear or branched alkyl or alkenyl radical having 7 to

21 carbon atoms,

n is an integer from 2 to 40,

0.01 to 5% by weight of an amine of the formula (II),

wherein

R ^{2 is} a linear or branched alkyl or alkenyl radical having 8 to

22 carbon atoms, the same or different from R ¹ ,

A represents an iminopropyl group -NH-CH ₂ -CH ₂ -CH ₂ -, an oxyethyl group -O-CH ₂ -CH ₂ - or an oxypropyl group -O-CH ₂ -CH (CH 3) -CH ₂ -

and

a is an integer from 0 to 5,

wherein the compound of formula (II) in the form of an ammonium salt can exist, and

(E) water. The pigment preparation according to the invention can moreover

(D) optionally 0 to 30% by weight of other auxiliaries customary for the preparation of aqueous pigment preparations, such as additional wetting agents, anionic dispersants, humectants, solvents, defoamers, rheology additives, preservatives, buffer substances,

pH regulators included.

The pigment preparations according to the invention are shear-resistant,

dryness resistant, storage-stable, little or no foaming during application and excellent rheology.

The component (A) of the pigment preparations according to the invention is

preferably a finely divided, inorganic white or colored pigment or a mixture of different inorganic pigments. Suitable inorganic

Examples of pigments are titanium dioxides, zinc sulfides, zinc oxides, iron oxides, magnetites, manganese iron oxides, chromium oxides, ultramarine, nickel or

Chromium antimony titanium oxides, manganese titanium rutiles, cobalt oxides, mixed oxides of cobalt and aluminum, rutile mixed phase pigments, rare earth sulfides, spinels of cobalt with nickel and zinc, spinels based on iron and chromium with copper zinc and manganese, bismuth vanadates and extender pigments.

In particular, 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 were used. Preference is also often given to using mixtures of inorganic pigments. Mixtures of organic and inorganic pigments are also common

used.

Component (B) of the pigment preparations according to the invention is a Fettsäureethanolamidethoxylat of Formula 1. R ¹ is preferably comprises 11 to 19 carbon atoms, n is preferably at least 3, especially at least equal to 4. It is preferably prepared by reacting fatty acids with ethanol amine to the fatty acid ethanolamide and subsequent addition of ethylene oxide using an alkaline catalyst such as sodium or potassium methylate. Starting from the fatty acid ethanolamide, ethylene oxide is preferably added to the terminal hydroxyl group. The addition of ethylene oxide to the nitrogen of the acid amide group is subordinated in a side reaction, so that the nitrogen of the acid amide group in lower

Scope can be bound to 2 Polyethylenglykoletherreste. Suitable fatty acids for the preparation of the fatty acid ethanolamides are capric acid, lauric acid, myristic acid, palmitic acids, margaric acid, stearic acid,

Arachic acid, behenic acid, palmitoic acid, oleic acid and naturally occurring mixtures such as palm kernel oil fatty acid, rapeseed oil fatty acid, sunflower oil fatty acid, soybean oil fatty acid or resin acids such as tall oil fatty acid. The fatty acids used as raw material can be saturated and unsaturated.

The component (C) of the pigment preparations according to the invention is in one embodiment a primary amine selected from the group of primary fatty amines having 8 to 22 carbon atoms, for example octylamine, decylamine, dodecylamine, tetradecylamine, coconut oil, soybean oil, stearylamine, oleylamine, tallow fatty alkylamine or behenylamine. R ² preferably comprises 12 to 20 carbon atoms. Furthermore, component (C) may be an alkylaminopropylamine obtained by addition of acrylonitrile to a primary fatty amine and

Hydrogenation can be produced. In particular, laurylaminopropylamine,

Oleylaminopropylamine and tallow fatty alkylaminopropylamine can be used. Further suitable amines (C) for the pigment preparations according to the invention are etheramines which can be prepared by aminolysis of fatty alcohol ethoxylates. Suitable etheramines are, for example, lauryloxethylamine, lauryldioxethylamine, isotridecyloxethylamine, isotridecyldioxethylamine and

Isotridecylpentaoxethylamin.

Component (C) may also be in the form of its ammonium salts, which may be Neutralization can be made with common organic and inorganic acids. Common acids can be, for example, hydrochloric acid,

Sulfuric acid, methanesulfonic acid, phosphoric acid, formic acid, acetic acid, propionic acid, lactic acid, oxalic acid, benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, cumoisulfonic acid and fatty acids having 6 to 22

Be carbon atoms.

The components (D) are further for the preparation of aqueous

Pigment preparations suitable auxiliary agents such as additional wetting agents, anionic dispersants, humectants, solvents, defoamers, rheology additives, preservatives, buffer substances and pH regulators.

Additional wetting agents may be wetting agents based on polysiloxane ethers, for example a methoxypolyethoxypropyltrisiloxane, alkynediolethoxylates and fluorosurfactants.

Suitable anionic dispersants are preferably anionic surfactants from the group of the sodium, potassium and ammonium salts of fatty acids,

Alkyl benzene sulfonates, alkyl sulfonates, olefin sulfonates, polynaphthalenesulfonates, alkyl sulfates, alkyl polyethylene glycol ether sulfates,

Alkyl phenol polyethylene glycol ether sulfates, sulfosuccinic acid esters,

Alkylpolyethylenglykoletherphosphorsäureester,

Alkyl polyethylene glycol ether carboxylic acids and their salts,

Sulfuric acid half esters and phosphoric esters of styrene-substituted

Phenol ethoxylates, styrene-substituted phenol polyethylene glycol ether carboxylic acids and their salts, sodium fatty acid isethionates, sodium fatty acid methylthaurides, and sodium fatty acid sarcosides.

Suitable humectants and solvents are preferably glycol ethers, which are understood here to mean compounds having ethoxy and / or propoxy groups which have average molecular weights of from 200 to 20,000 g / mol, in particular polyethylene glycol ethers or polypropylene glycol ethers having an average molecular weight of from 200 to 20,000 g / mol, mono , Di- or Triethylene glycol, mono-, di- or tripropylene glycol, methyl, ethyl-propyl, butyl or higher alkylpolyalkylene glycol ethers having 1, 2, 3 or more

Ethylene glycol or propylene glycol units such as, for example, methoxypropanol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether,

Ethylene glycol monobutyl ether, diethylene glycol monobutyl ether,

Butyl polyethylene glycol ether, propylene polyethylene glycol ether,

Ethyl polyethylene glycol ethers, methyl polyethylene glycol ethers,

Dimethylpolyethylene glycol ethers, dimethylpolypropylene glycol ethers,

Glycerol ethoxylates having a molecular weight of from 200 to 20,000 g / mol, pentaerythritol alkoxylates having a molecular weight of from 200 to 20,000 g / mol, or further ethoxylation and alkoxylation products and random or block copolymers prepared by addition of ethylene oxide and / or propylene oxides to monohydric and higher alcohols were, with a molecular weight of 200 to 20,000 g / mol. Average molecular weight / molecular weight means number average molecular weight / molecular weight.

Other suitable auxiliaries of the aqueous according to the invention

Pigment preparations are preferably water-soluble organic or hydrotropic substances which optionally also serve as solvents.

Particularly suitable are, for example, formamide, urea,

Tetramethylurea, ε-caprolactam, glycerol, diglycerol, polyglycerol,

N-methylpyrrolidone, 1, 3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzenesulfonate, sodium xylenesulfonate, sodium toluenesulfonate, sodium cumene sulfonate, sodium dodecylsulfonate, sodium benzoate, sodium salicylate, sodium butylmonoglycol sulfate.

Suitable defoamers are preferably mineral oil defoamers and emulsions thereof, silicone oil defoamers and silicone oil emulsions, polyalkylene glycols, polyalkylene glycol fatty acid esters, fatty acids, higher-value alcohols,

Phosphoric acid ester, hydrophobically modified silica, aluminum tristearate,

Polyethylene waxes and amide waxes.

Suitable rheology additives as viscosity modifiers are e.g. B. Starch and cellulose derivatives and hydrophobically modified ethoxylated urethanes (HEUR) thickeners, alkali-swellable acrylate thickeners, hydrophobically modified acrylate thickeners, polymers of acrylamidomethylpropanesulfonic acid,

Benthonite thickener or fumed silica.

Pot preservatives are added to stabilize the aqueous pigment preparations and to prevent the uncontrolled proliferation of bacteria, algae and fungi. Suitable biocides are formaldehyde, formaldehyde-releasing components, methylisothiazolinone, chloromethylisothiazolinone,

Benzisothiazolinone, bronopol, dibromodicyanone butane and

silver chloride-coated titanium dioxide.

As buffer substances and pH regulators preferably organic or inorganic bases and acids are used. Preferred organic bases are amines, such as. Ethanolamine, diethanolamine, triethanolamine,

Ν, Ν-dimethylethanolamine, diisopropylamine, 2-amino-2-methyl-1-propanol or dimethylaminomethylpropanol. Preferred inorganic bases are sodium, potassium, lithium hydroxide or ammonia. Water used to prepare the aqueous pigment preparations according to the invention, component (E), is preferably used in the form of distilled or demineralized water. Also drinking water (tap water) and / or water of natural origin can be used. Water is preferably contained in the aqueous pigment preparation according to the invention to 10 to 65 wt .-%, in particular ad 100 wt .-%.

The aqueous pigment preparations according to the invention preferably have a viscosity of 10 to 10,000 mPas, preferably 50 to 5,000 mPas and particularly preferably 300 to 3,000 mPas, measured with a cone-and-plate viscometer at a shear rate of 1/60 sec ^-1 , eg a Haake Viscometer 550 from Thermo Haake.

The aqueous pigment preparations of the invention are in each Mixable with water, whereby several different preparations can be mixed with water. They are distinguished from conventional pigment preparations by excellent storage stability and good rheological properties.

The present invention also provides a process for the preparation of the pigment preparations according to the invention by reacting component (A) in the form of powder or granules in the presence of water (E) and the

Components (B), (C) and optionally (D) in a conventional manner

dispersed, then optionally further water (E) admixed and the resulting aqueous pigment dispersion with water to the desired

Concentration sets. The components (B), (C), if appropriate (D) and (E) are preferably mixed and homogenized, then the component (A) is stirred into the initially introduced mixture, the pigment being pasted in and predispersed. Depending on the grain hardness of the pigments used

then optionally with cooling by means of a grinding or

Dispergieraggregats finely dispersed or finely divided. For this purpose, agitators, dissolvers (sawtooth), rotor-stator mills, ball mills,

Agitator ball mills such as sand and pearl mills, high-speed mixers,

Knetapparaturen, roll mills or high performance bead mills are used. The fine dispersion or milling of the pigments takes place up to the desired particle size distribution and can be carried out 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 with water, preferably deionized or distilled water, further diluted.

The pigment preparations according to the invention are suitable for pigmenting and dyeing macromolecular materials of all kinds. The pigment preparation according to the invention are suitable for pigmenting or producing paints and dispersion paints, dispersion paints, printing inks, in this case for example textile printing inks, flexographic printing inks, decor printing or gravure printing inks, wallpaper paints , water-dilutable paints, wood stains, wood protection systems and paints for surface coating of articles of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or

Rubber are used. A further advantage of the fatty acid ethanolamide ethoxylates according to the invention is the labeling of the mixtures according to the European regulation

2008-1272 EC on the classification, labeling and packaging of substances and mixtures. This regulation 2008-1272 EC writes within the

European Community, mixtures containing> 1% of a corrosive or> 3% of an irritating surfactant are classified as hazardous.

It is therefore advantageous to use surfactants that do not irritate the skin or mucosa or have a corrosive effect. A variety of nonionic surfactants such as the oleyl / cetyl ethoxylate used in Example 2 (Comparative Example) causes severe eye damage. This leads to a marking of the pigment preparation according to Example 2, while the fatty acid ethanolamide ethoxylate used in Example 1 and also the mixture according to the regulation 2008-1272 EC is not classified as hazardous.

Examples

Preparation of a pigment preparation

The pigment, either as a powder, granules or as press cake, is made into a paste together with the dispersants and the other additives in deionized water and then treated with a dissolver (for example from VMA Getzmann GmbH, type AE3-M1) or a homogenized and predispersed to other suitable apparatus. Subsequent fine dispersion takes place with the aid of a bead mill (eg with AE3-M1 from VMA-Getzmann) or another suitable dispersing aggregate, the grinding with silver quartzite beads or zirconium mixed oxide beads of size d = 1 mm with cooling to room temperature

desired color intensity and coloristic takes place. The dispersion is then adjusted to the desired final pigment concentration with deionized water, the grinding media are separated off and the pigment preparation is isolated. The pigment preparations described in the following examples were prepared by the previously described procedure, with the following

Ingredients in the indicated amounts were used so that 00 parts of the respective pigment preparation arise. In the present application "parts" parts by weight and percentages by weight, unless otherwise stated in an individual case.

example 1

70 parts of CI Pigment Red 101 (Bayferrox ^® Red 130, Fa. Lanxess

Component (A)),

4 parts of tall oil fatty acid ethanolamide reacted with 5 moles of ethylene oxide

(Component (B)),

0.6 parts tallow alkylamine (Genamin ^® TA 100, Fa. Clariant, component

(C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)), 0.2 parts of acetic acid, 99% (component (D)),

0.3 parts defoamer (D-Foam-R C 741, Fa. Clariant, component (D)), 0.2 parts of a preservative (Nipacide ^® BSM, Fa. Clariant, component

(D)),

14.7 parts water (component (E))

In a grinding container, the components (B), (C), (D) and (E) are presented and mixed. Subsequently, the powdery component (A) is added and predispersed with the dissolver. The fine dispersion takes place in a bead mill by means of zirconium mixed oxide beads of size d = 1 mm with cooling. Subsequently, the grinding media are separated and the pigment preparation is isolated. The pigment preparation is stored for one week at 60 ° C and visually assessed. The viscosity of the pigment preparation is measured with a Haake Viscometer 550 at a shear rate of 1/60 sec ^-1 .

The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of the pigment preparation is 1679 mPa s.

Example 2 (comparative example)

70 parts of CI Pigment Red 101 (Bayferrox Red 130, component (A)), 4 parts of Oleyl / Cetylethoxylat with 8 moles of ethylene oxide (Genapol ^® O 080, Fa.

Clariant, component (B))

0.6 parts of tallow fatty alkylamine (Genamin TA 100, Clariant, component (C)) 10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(D)),

18 parts water (component (E))

It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation after grinding is a liquid, foam-free pigment dispersion. The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of the pigment preparation is 1677 mPa.s. Due to the European

Regulation 2008-1272 EC on the Classification, Labeling and Packaging of Substances and Mixtures, however, would require the pigment preparation according to Example 2 to be labeled because the oleyl / cetyl ethoxylate used here can cause severe eye damage.

Example 3 (comparative example)

70 parts C.I. Pigment Red 101 (Bayferrox Red 130, component (A)), 1.5 parts of an aqueous, 40% solution of a sodium polyacrylate having an average molecular weight of 7000 g / mol instead of the combination of components (B) and (C),

0 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)), 0.3 parts defoamer (D-Foam-R C 741, Fa. Clariant, component (D)), 0.2 parts of preservative (Nipacide BSM, Clariant, component (D)),

18 parts of water (component (E)) The procedure is as in Example 1 during the preparation and testing of the pigment preparation. The pigment preparation after grinding is a liquid, foam-free pigment dispersion. After one week of storage at 60 ° C, the dispersion is stiffened to a solid gel. By stirring, the dispersion can be re-liquefied and has a viscosity of 855 mPa · s, but the pigment dispersion solidifies after further storage for 4 weeks at room temperature to a solid gel.

Example 4 (Comparative Example)

70 parts C.I. Pigment Red 101 (Bayferrox Red 130, component (A)), 4 parts EO / PO block copolymer with 20% ethylene oxide (Genapol PF 20,

Fa. Clariant, component (B)),

0.6 parts of tallow fatty alkylamine (Genamin TA 100, Clariant, component (C)), 10 parts of polyethylene glycol having a molecular weight of 200 g / mol

0.3 part of defoamer (D-Foam-R C 741, Clariant, component (D)), 0.2 parts of preservative (Nipacide BSM, Clariant, Component

(D)),

18 parts water (component (E))

It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation after grinding is a liquid, foam-free pigment dispersion. The pigment preparation has formed after one week storage at 60 ° C a sediment. The viscosity of the pigment preparation is 671 mPa-s. Example 5 (Comparative Example)

70 parts C.I. Pigment Red 101 (Bayferrox Red 130, component (A)), 4 parts of coconut fatty acid ethoxylates with 10 moles of ethylene oxide (Genagen® C 00,

Fa. Clariant, component (B)),

0.3 part of defoamer (D-Foam-R C 741, Clariant, component (D)), 0.2 parts of preservative (Nipacide® BSM, Clariant, Component

(D)),

18 parts water (component (E))

It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation after grinding is a liquid, foam-free pigment dispersion. The pigment preparation has formed after one week storage at 60 ° C a sediment. The viscosity of the pigment preparation is 51 1 mPa-s. Example 6

70 parts C.I. Pigment White 6 (Kronos Titanium Dioxide 2160, Kronos,

Component (A)),

(Component (B)),

1 part of lauryldioxypropylamine, a reaction product of a Ci2 / Ci ₄

Fatty alcohol with 2 moles of propylene oxide and subsequent aminolysis to give the primary alkylpolyoxypropylamine amine (Genamin LA2P 100 D, Clariant, component (C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)),

(D)), Parts of water (component (E))

It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of

Pigment preparation is 1531 mPa-s.

Example 7

65 parts C.I. Pigment Yellow 42 (Bayferrox Yellow 3920, Fa. Lanxess,

Component (A)),

4 parts alkoxylate consisting of a saturated C16 / C18 fatty alcohol reacted with 7 moles of propylene oxide and 9 moles of ethylene oxide

(Component (B)),

1 part C12 C16 coconut fatty alkylamine (Genamin CC 100, Clariant,

Component (C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)), 0.3 parts of defoamer (D-Foam-R C 741, Fa. Clariant, component (D)), 0.2 parts of preservative (Nipacide BSM, Fa. Clariant, component

(D)),

19.5 parts of water (component (E))

Pigment preparation is 2246 mPa-s.

Example 8

70 parts C.I. Pigment Green 17 (Chrome Oxide Green, Fa. Lanxess,

Component (A)),

6 parts of alkoxylate consisting of a saturated C16 / C18 fatty alcohol reacted with 7 moles of propylene oxide and 7 moles of ethylene oxide

(Component (B)), 1 part C ₂ / C 16 coconut fatty alkylamine (Genamin CC 100, Clariant, component (C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(D)),

12.5 parts of water (component (E)). The preparation and testing of the pigment preparation are carried out as described in Example 1. The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of

Pigment preparation is 1995 mPa-s. Example 9

65 parts of CI Pigment Blue 28 (HEUCODUR ^® Blue 551, Fa. Heubach,

Component (A)),

6 parts of alkoxylate consisting of a saturated C | ₆ / C ₈ fatty alcohol reacted with 7 moles of propylene oxide and 7 moles of ethylene oxide

(Component (B)),

1 part C12 / C16 coconut fatty alkylamine (Genamin CC 100, Fa. Clariant,

Component (C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(D)),

17.5 parts of water (component (E)). The preparation and testing of the pigment preparation are carried out as described in Example 1. The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of

Pigment preparation is 1675 mPa-s. Example 10

70 parts of CI Pigment Yellow 184 (Yellow Sicopal ^® L 110, Fa. BASF,

Component (A)),

(Component (B)),

1 part C ₂ / Ci6 coconut fatty alkylamine (Genamin CC 100, Fa. Clariant,

Component (C)),

10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(D)),

12.6 parts of water (component (E))

Pigment preparation is 1542 mPa-s.

Example 11

70 parts of CI Pigment Red 101 (Bayferrox ^® Red 130, Fa. Lanxess

Component (A)),

6 parts of tall oil fatty acid ethanolamide reacted with 10 moles of ethylene oxide

(Component (B)),

1 part of coconut fatty amine (Genamin ^® CC 100, Fa. Clariant, component (C)), 10 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)), 0.3 parts of defoamer (D-Foam-R C 741, Fa. Clariant, component (D)), 0.2 parts of preservative (Nipacide ^® BSM, Fa Clariant, component

(D)),

12.5 parts of water (component (E)) It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation is liquid after one week storage at 60 ° C, homogeneous and foam-free. The viscosity of

Pigment preparation is 1967 mPa-s.

Example 12

70 parts of CI Pigment Red 101 (Bayferrox ^® Red 130, Fa. Lanxess

Component (A)),

6 parts of tall oil fatty acid ethanolamide reacted with 15 moles of ethylene oxide

(Component (B)),

(D)),

12.5 parts of water (component (E))

Pigment preparation is 1285 mPa-s. Example 13

65 parts of CI Pigment Yellow 42 (Yellow Bayferrox ^® 3920, Fa. Lanxess

Component (A)),

(Component (B)),

(Polyglycol 200 USP, Fa. Clariant, component (D)), 0.3 parts defoamer (D-Foam-R C 741, Fa. Clariant, component (D)), 0.2 parts of preservative (Nipacide ^® BSM, Fa. Clariant, component (D)),

Pigment preparation is 1053 mPa-s. Example 14

65 parts of CI Pigment Yellow 42 (Yellow Bayferrox ^® 3920, Fa. Lanxess

Component (A)),

(Component (B)),

(D)),

17.5 parts of water (component (E))

Pigment preparation is 1365 mPa-s.

Example 15

65 parts of CI Pigment Black 11 (Bayferrox ^® Black 316, Fa. Lanxess

Component (A)),

(Component (B)),

(D)),

17.5 parts of water (component (E))

Pigment preparation is 1103 mPa-s.

Example 16

65 parts of CI Pigment Black 11 (Bayferrox ^® Black 316, Fa. Lanxess

Component (A)),

(Component (B)),

1 part of coconut fatty amine (Genamin ^® CC 100, Fa. Clariant, component (C)), 0 parts of polyethylene glycol having a molecular weight of 200 g / mol

(Polyglycol 200 USP, Fa. Clariant, component (D)),

(D)),

17.5 parts of water (component (E))

Pigment preparation is 844 mPa-s. Example 17

70 parts of Cl Pigment White 6 ( ^Kronos® Titanium Dioxide 2160, Kronos,

Component (A)),

(Component (B)),

(D)),

12.5 parts of water (component (E))

Pigment preparation is 1539 mPa-s.

Example 18

70 parts of Cl Pigment White 6 ( ^Kronos® Titanium Dioxide 2160, Kronos,

Component (A)),

(Component (B)),

(D)),

12.5 parts of water (component (E))

It is carried out in the preparation and testing of the pigment preparation as described in Example 1. The pigment preparation is after one week Storage at 60 ° C liquid, homogeneous and foam-free. The viscosity of the pigment preparation is 633 mPa.s.

Claims

claims:

1. Aqueous pigment preparations containing (A) 30 to 75 wt .-% of at least one inorganic white or

Colored pigment or a mixture of different inorganic white or colored pigments,

wherein

R ^{1 is} a linear or branched alkyl or alkenyl radical having 7 to

21 carbon atoms,

n is an integer from 2 to 40,

0.01 to 5% by weight of at least one amine of the formula (II),

R ² ^ T TN

wherein

R ^{2 is} a linear or branched alkyl or alkenyl radical having 8 to

22 carbon atoms, the same or different from R ¹ ,

A is an iminopropyl group -NH-CH ₂ -CH ₂ -CH ₂ -, an oxyethyl group

Is -O-CH ₂ -CH ₂ - or an oxypropyl group -O-CH ₂ -CH (CH ₃ ) -CH ₂ -

and a is an integer from 0 to 5,

wherein the compound of formula (II) may be in the form of an ammonium salt, and (E) water.

2. An aqueous pigment preparation according to claim 1, wherein the

Fatty acid ethanolamide ethoxylate of the formula (I) was prepared by addition of ethylene oxide to a fatty acid ethanolamide and n is an integer from 3 to 40.

3. Aqueous pigment preparation according to claim 1 and / or 2, wherein A is -NH-CH 2 -CH 2 -CH 2 and a is 1.

4. Aqueous pigment preparation according to one or more of claims 1 to 3, wherein A is -O-CH ₂ -CH ₂ - or -O-CH ₂ -CH (CH ₃ ) -CH ₂ - and a is an integer of 1 to 5 stand.

5. Aqueous pigment preparation according to one or more of claims 1 to 4, containing 1 to 10 wt .-% of a Fettsäureethanolamidethoxylats the

Formula (I).

6. Aqueous pigment preparation according to one or more of claims 1 to 5, containing 0.1 to 2 wt .-% of an amine of formula (II).

7. Aqueous pigment preparation according to claim 6, wherein in formula (II) a = 0.

8. Aqueous pigment preparation according to one or more of claims 1 to 7, containing 10 to 65 wt .-% water.

The aqueous pigment preparation according to one or more of claims 1 to 8, wherein R ¹ comprises 11 to 19 carbon atoms.

10. Aqueous pigment preparation according to one or more of claims 1 to 9, wherein R ² comprises 12 to 20 carbon atoms.

11. Aqueous pigment preparation according to one or more of claims 1 to 10, which has a viscosity of 10 to 10,000 mPas, determined with a cone-plate viscometer at a shear rate of 1/60 sec ^-1 .

12. Aqueous pigment preparations according to one or more of claims 1 to 11, comprising

(D) to 30 wt .-% more, for the production of aqueous

Pigment preparations customary auxiliaries selected from wetting agents, anionic dispersants, humectants, solvents,

Defoamers, rheology additives, preservatives,

Buffer substances, pH regulators.

13. An aqueous pigment preparation according to claim 12, containing up to

15% by weight of at least one humectant or solvent selected from glycol ethers having 200 to 20,000 g / mol average molecular weight.

14. Aqueous pigment preparation according to claim 12 and / or 13, containing up to 2 wt .-% defoamer.

15. Aqueous pigment preparation according to one or more of claims 12 to 14, containing up to 1 wt .-% of a pot preservative.

16. Use of an aqueous pigment preparation according to one or more of claims 1 to 15 for coloring macromolecular

Materials, coating materials, paints and inks and their use for printing on two-dimensional fabrics.