WO2009024232A1 - Wässrige pigmentpräparationen mit anionischen additiven auf allyl- und vinyletherbasis - Google Patents
Wässrige pigmentpräparationen mit anionischen additiven auf allyl- und vinyletherbasis Download PDFInfo
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- WO2009024232A1 WO2009024232A1 PCT/EP2008/006020 EP2008006020W WO2009024232A1 WO 2009024232 A1 WO2009024232 A1 WO 2009024232A1 EP 2008006020 W EP2008006020 W EP 2008006020W WO 2009024232 A1 WO2009024232 A1 WO 2009024232A1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/131—Glass, ceramic, or sintered, fused, fired, or calcined metal oxide or metal carbide containing [e.g., porcelain, brick, cement, etc.]
Definitions
- the present invention relates to aqueous pigment preparations containing novel anionic polymers as dispersants, and to their use for coloring natural and synthetic materials.
- Dispersants are usually necessary for the dispersion of pigments in the liquid medium.
- Dispersing agents of particular commercial importance are, for example, for the dispersion of pigments in the preparation of pigment concentrates which are used for coloring dispersion and enamel paints, paints, coating materials and printing inks, and for coloring paper and paper pulp, cardboard and textiles.
- the prior art also describes pigment preparations which contain ordered polymer structures. Examples of these are EP 1 293 523, DE 10 2005 012 315 and EP 1 721 941.
- novolak dispersants contain radicals of alkylphenols, frequently nonylphenol, and their ethoxylates. Since Alkylphenolethoxylate or their degradation products are hardly degraded in the environment, they accumulate. This is problematic because they have a hormonal effect on aquatic organisms. Therefore, legislation has been adopted in many countries (eg 2003/53 / EC) restricting or prohibiting the use of substances containing alkylphenols or their ethoxylates in open material cycles. Previous research has shown that it is still extremely difficult to synthesize dispersants that are equivalent in performance to anionic novolac systems.
- new dispersants are required which are able to disperse low-viscosity organic pigments in a high concentration of more than 40%.
- the dispersions must be easy to prepare, ie.
- the pigments must be readily wettable and easily incorporated into the aqueous medium.
- the dispersion must have a high and reproducible color strength and keep it stable over a period of several years. Likewise, all other coloristic parameters such. As the hue angle and purity can be reproduced and stable.
- the dispersion must have a low viscosity;
- the pigments must neither agglomerate nor flocculate, nor may they float or sediment.
- the dispersion should not foam or cause or accelerate foaming in the application medium.
- the dispersants should contribute to a broad compatibility of the dispersions in various application media.
- the dispersion must be shear stable, ie. Under shear, the color intensity or coloristic must not change and the dispersion must remain flocculation-stable under these conditions.
- the present invention relates to aqueous pigment preparations containing
- B is a C 2 to C 4 alkylene other than A, k is 0 or 1, m is a number from 0 to 500, preferably 0 to 50; n is a number from 0 to 500, preferably 0 to 50, where the sum m + n is 1 to 1000; X a is an aromatic or araliphatic radical having 3 to 30 C atoms, which optionally contains one or more of the heteroatoms N, O and S,
- Z a is H or (C r C 4 ) alkyl
- Z b is H or (C 1 -C 4 ) alkyl
- Z c is H or (C 1 -C 4 ) alkyl
- R 1 is hydrogen or methyl
- Xb is an aromatic or araliphatic radical having 3 to 30 C atoms, which optionally contains one or more of the heteroatoms N, O and S,
- W 3 is oxygen or the group NH
- R 2 is hydrogen or methyl
- Y is an aliphatic hydrocarbon radical having 1 to
- M is H, a monovalent metal cation, a divalent metal cation, NH 4 + , a secondary, tertiary or quaternary ammonium ion, or a combination thereof, or equivalents of di-, trivalent or polyvalent metal ions such as Ca 2+ or Al 3+ (the star * indicates in the Markush formula that there is a link to the polymer at this point);
- Preferred pigment preparations contain from 5 to 80% by weight, for example from 10 to 70% by weight, of component (A).
- Preferred pigment preparations contain from 0.1 to 30% by weight, for example from 2 to 15% by weight, of component (B).
- Particularly preferred pigment preparations comprise component
- the minimum concentration is independently of each other suitably at least 0.01 wt .-%, preferably at least 0.1 wt .-% , based on the total weight of the pigment preparation.
- the component (A) of the pigment preparation according to the invention is a finely divided organic or inorganic pigment or a mixture of various organic and / or inorganic pigments.
- the component (A) may also be a dye which is soluble in certain solvents and has pigment character in other solvents.
- the pigments can be used both in the form of dry powder and as water-moist press cake.
- organic pigments there are monoazo, disazo, laked azo, ⁇ -naphthol, naphthol AS, benzimidazolone, disazo condensation, azo metal complex pigments and polycyclic pigments, e.g. Phthalocyanine, quinacridone, perylene, perinone, thioindigo, anthanthrone, anthraquinone, flavanthrone, indanthrene, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, isoindolinone, isoindoline and diketopyrrolopyrrole pigments or carbon blacks into consideration.
- Phthalocyanine quinacridone, perylene, perinone, thioindigo, anthanthrone, anthraquinone, flavanthrone, indanthrene, isoviolanthrone, pyranthrone, dioxazine, quinophthalone, iso
- those which are as finely divided as possible for the preparation of the preparations are particularly suitable, with preferably 95% and particularly preferably 99% of the pigment particles having a particle size ⁇ 500 nm.
- organic pigments are carbon black pigments, such as gas or Furnaceruße; 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, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Yellow, Pigment Pigment 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; ⁇ -naphthol and nap
- Pigment Orange 43 Triarylcarboniumpigmente, 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.
- laked dyes such as Ca, Mg, Al lacquers of dyes containing sulfonic acid and / or carboxylic acid groups.
- suitable inorganic 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 as well as manganese, bismuth vanadate and extender pigments.
- Pigment Black 11, Pigment Black 33 and Pigment White 6 are used. Preference is also often given to using mixtures of inorganic pigments. Mixtures of organic and inorganic pigments are also commonly used.
- pigment dispersions can also be prepared dispersions containing as solids, for example, natural finely divided ores, minerals, difficult or insoluble salts, wax or plastic particles, dyes, crop protection and pesticides, UV absorbers, optical brighteners and polymerization stabilizers.
- the copolymers (component B) have a molecular weight of from 10 3 g / mol to 10 9 g / mol, more preferably from 10 3 to 10 7 g / mol, particularly preferably from 10 3 to 10 5 g / mol.
- These polymers can be prepared by conventional methods of free radical polymerization of monomers corresponding to those described in brackets [] c. [] b and [] a described radicals in formula (I), (II), (III) or (IV) are prepared. Following the polymerization, the nonionic polymer thus obtained is converted to anionic functionalities.
- Preferred monomers of the group [] a are those in which A is ethylene and B is propylene, or A is propylene and B is ethylene.
- the alkylene oxide units (AO) m and (BO) n can be either random or, as in the case of a preferred embodiment, arranged in a block.
- the monomers of group [] b include, for example, the following esters and amides of acrylic acid and methacrylic acid: phenyl, benzyl, toIyI, 2-phenoxyethyl, phenethyl.
- Further monomers of group [] b are vinylaromatic monomers such as styrene and its derivatives such as vinyltoluene, alpha-methylstyrene.
- the aromatic moiety can also be heteroaromatics, such as.
- Particularly preferred monomers of group [] b may be: styrene, 1-vinylimidazole, benzyl methacrylate, 2-phenoxyethyl methacrylate and phenethyl methacrylate.
- the monomers of group [] c include, for example, the following esters and amides of acrylic acid and methacrylic acid: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl , 2-ethylhexyl, 3,3-dimethylbutyl, heptyl, octyl, isooctyl, nonyl, lauryl, cetyl, stearyl, behenyl, cyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, bornyl , Isobornyl, adamantyl, (2,2-dimethyl-1-methyl) propyl, cyclopentyl, 4-ethylcyclohexyl, 2-ethoxyethyl, tetrahydrofurfuryl and tetrahydro
- the monomers of group [] c include the vinyl esters of carboxylic acids, such as vinyl laurate, vinyl myristate, vinyl stearate, behenic, pivalic, neohexanoic, neoheptanoic, neooctanoic, neononanoic and neodecanoic vinyl esters.
- the vinyl esters can also be used from mixtures of such carboxylic acids.
- Preferred monomers of the group [] c are the following alkyl esters or alkyl amides of acrylic acid and methacrylic acid: methyl, ethyl, propyl, butyl, Isobutyl, 2-ethoxyethyl, myristyl, octadecyl, more preferably 2-ethylhexyl and lauryl.
- component (C) usually cationic, anionic, amphoteric or non-ionic compounds are used which promote the pigment wetting (wetting agents, wetting agents), for example alkyl sulfates such. As lauryl sulfate, alkyl benzene sulfonic acid, short chain alkoxylation products such. B. lauryl alcohol reacted with about 5 moles of ethylene oxide or alkynediols.
- Component (D) of the pigment preparations of the invention are customary dispersants suitable for the preparation of aqueous pigment dispersions and surfactants or mixtures of such substances.
- anionic, cationic, amphoteric or nonionic surface-active compounds are used, as described in DE-A-10 2007 021 870.
- Component (E) corresponds to organic solvents or water-soluble hydrotropic substances.
- Hydrotropes which optionally also serve as solvents, or are of oligomeric or polymeric nature are, for example, formamide, urea, tetramethylurea, ⁇ -caprolactam, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, ⁇ -methyl- ⁇ -hydroxy-polyethylene glycol ethers, dimethyl polyethylene glycol ethers , Dipropylene glycol, polypropylene glycol, dimethylpolypropylene glycol ethers, copolymers of ethylene glycol and propylene glycol, butyl glycol, methyl cellulose, glycerol, diglycerol, polyglycerol, N-methylpyrrolidone, 1,3-diethyl-2-imidazolidinone, thiodiglycol, sodium benzenesulfonate, sodium xylenesulfonate, sodium
- thickeners, preservatives, viscosity stabilizers, grinding aids and fillers are used as component (F).
- customary additives may be antisettling agents, light stabilizers, antioxidants, degasifiers / defoamers, foam-reducing agents, anti-caking agents and additives which favorably influence viscosity and rheology.
- polyvinyl alcohol and cellulose derivatives in question Water-soluble natural or synthetic resins and polymers as film formers or binders for increasing adhesion and abrasion resistance are also possible.
- pH regulators organic or inorganic bases and acids are used. Preferred organic bases are amines, such as.
- ethanolamine diethanolamine, triethanolamine, N, N-dimethylethanolamine, diisopropylamine, aminomethylpropanol or dimethylaminomethylpropanol.
- Preferred inorganic bases are sodium, potassium, lithium hydroxide or ammonia.
- Component (F) may also correspond to fats and oils of plant and animal origin, for example beef tallow, palm kernel fat,
- saturated and unsaturated higher fatty acids are common additives, eg. B. palmitic acid, Cyprylic acid, capric acid, myristic acid, lauric acid,
- Water used to prepare the pigment preparations, component (G), is preferably used in the form of desalted or distilled water. Also drinking water (tap water) and / or water of natural origin can be used.
- the present invention also provides a process for preparing the pigment preparations of the invention, which comprises reacting component (A) in the form of powder, granules or aqueous presscake in the presence of water (G) and components (B) and optionally (C ) and (D), then optionally water (G), and if appropriate, one or more of components (E) and (F) is admixed and, if appropriate, the aqueous pigment dispersion obtained is diluted with water (G).
- the components (B) and optionally one or more of the components (C), (D), (E) and (F) are first mixed and homogenized, then the component (A) is stirred into the initially introduced mixture, the component ( A) is pasted and predispersed. Depending on the grain hardness of the component (A) is then optionally finely dispersed or finely divided with cooling with the aid of a grinding or dispersing.
- agitators dissolvers (sawtooth), rotor-stator mills, ball mills, stirred ball mills such as sand and bead mills, high-speed mixers, kneaders, roller mills or high performance bead mills can be used.
- the fine dispersion or grinding of component (A) takes place up to the desired particle size distribution and can be carried out at temperatures in the range of 0 to 100 0 C, advantageously at a temperature between 10 and 70 0 C, preferably at 20 to 60 0 C.
- the pigment preparation can be further diluted with water (G), preferably deionized or distilled water.
- the pigment preparations according to the invention are suitable for pigmenting and dyeing natural and synthetic materials of all kinds, in particular aqueous paints, dispersion and enamel paints (dispersion paints), for paper pulp dyeing and for laminating and dyeing.
- the pigment preparations according to the invention are suitable for coloring macromolecular materials of all kinds, for. B. of natural and synthetic fiber materials and preferably cellulose fibers.
- Further applications are the production of printing inks, here for example textile printing, flexoprinting, decorative printing or gravure printing inks, wallpaper paints, waterborne paints, wood protection systems, viscose spin dyes, paints, also powder coatings, sausage casings, seeds, fertilizers, glass, in particular glass bottles, as well as for Mass coloration of roof tiles, for coloring for plasters, concrete, wood stains, colored pencil leads, felt-tip pens, waxes, paraffins, inks, pens for ballpoint pens, chalks, detergents and cleaners, shoe care products, latex
- 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 resin
- 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, silicone resins, individually or in mixture.
- 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, silicone resins, individually or in mixture.
- the pigment preparations according to the invention are suitable for the production of printing inks for use in all conventional ink-jet printers, in particular for those based on the bubble jet or piezo process. These printing inks can be used to print on paper, as well as natural or synthetic fiber materials, films and plastics.
- the pigment preparations of the invention can be used for printing various types of coated or uncoated substrate materials, such. As for printing on cardboard, cardboard, wood and wood-based materials, metallic materials, semiconductor materials, ceramic materials, glasses, glass and ceramic fibers, inorganic materials, concrete, leather, food, cosmetics, skin and hair.
- the substrate material may be two-dimensionally flat or spatially extended, d. H. be designed in three dimensions and both completely or only partially printed or coated.
- the pigment preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as.
- electrophotographic toners and developers such as.
- one- or two-component powder toners also called one- or two-component developer
- magnetic toner liquid toner
- latextoner polymerization toner
- special toners such as one- or two-component powder toners, magnetic toner, liquid toner, latextoner, polymerization toner and special toners.
- the pigment preparations of the invention as colorants in inks, preferably ink-jet inks, such as. B. on aqueous or non-aqueous Solvent-based, microemulsion inks, UV-curable inks and in such inks, which work according to the hot-melt method suitable.
- the pigment preparations according to the invention can also be used as colorants for "color filters” for “Fiat Panel Displays", for both the additives and the subtractive color generation, also for “photo-resists”, and as colorants for electronic inks ("Electronic Inks “or” e-inks ”) or electronic paper (“ electronic paper “or” e-paper ”) are used.
- the monomer A, monomer C and, if appropriate, the molecular weight regulator and component 1 (ascorbic acid) of the redox initiator system were initially charged in a solvent under nitrogen. Then The temperature was brought to 80 0 C with stirring and metered in a solution of the component 2 (t-BuOOH) of the redox initiator system within three hours. At the same time, dosing of monomer B started, which was completed after 3 hours. Subsequently, stirring was continued for 2 hours at this temperature, then the solvent was removed in vacuo.
- the copolymer was placed under nitrogen in a flask containing sulfamic acid and urea. Then, it was heated to 100 ° C with stirring for 4 hours. Subsequently, the pH was adjusted to 6.5 to 7.5 with 50% strength by weight sodium hydroxide solution. By NMR spectroscopy, a degree of conversion of> 95% to the corresponding sulfuric acid ester ammonium salt was determined.
- the copolymer was placed under nitrogen in a flask. Then, maleic anhydride and sodium hydroxide were added and heated with stirring to a temperature of 75 to 85 0 C. The mixture was stirred at this temperature for three hours and then aqueous sodium sulfite solution (10% strength by weight) was added. At 60 to 70 0 C was stirred until the completion of the reaction and finally the pH adjusted to pH 7 with 50 wt .-% sodium hydroxide solution.
- the pigment either as a powder, granules or as a presscake, was made into a paste in deionized water together with the dispersants and other additives and then treated with a dissolver (e.g.
- VMA-Getzmann GmbH type AE3-M1 or other suitable apparatus homogenized and predispersed.
- the dispersion was then adjusted to the desired final pigment concentration with deionized water, the grinding media were separated off and the pigment preparation was isolated.
- the color strength and hue were determined in accordance with DIN 55986.
- the emulsion paint was applied to a lacquer card after mixing with the pigment dispersion, followed by rubbing with a finger on the lower part of the lacquer card if the rubbed area is then more strongly colored than the adjoining, non-aftertreated area (the rub-out test is described in DE 2 638 946).
- the tinting strength and the compatibility with the medium to be inked were determined using a dispersion paint for exterior paints (water-based, 20% TiO 2 ).
- a pulp suspension was dyed 10% with the pigment preparation, from it produced by drying and pressing a solid paper and determined in the following color strength and color.
- the shear stability of the pigment preparations was determined by flocculating the pigment particles of the dispersion in a pulp suspension with the aid of cationic epichlorohydrin resins. The shearing was carried out with the aid of a commercially available kitchen mixer (here Braun MX 32) while setting a high rotational speed. Subsequently, paper was made from the pulp and the color strength of a sheared to a non-sheared dispersion was compared.
- the viscosity was measured using a cone-plate viscometer (Roto Visco 1) Haake at 20 0 C (titanium cone: 0 60 mm, 1 °), the dependence of viscosity on the shear rate in a range between 0 and 200 s '1 was examined. The viscosities were measured at a shear rate of 60 s -1 .
- the viscosity was measured immediately after preparation of the preparation, and after storage at 50 ° C. for four weeks.
- the pigment preparations described in the following examples were prepared by the method described above, using the following constituents in the stated amounts in such a way that 100 parts of the respective pigment preparation are formed. In the following examples, parts are parts by weight.
- the following general recipe applies: X parts component (A), pigment
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/674,137 US8202361B2 (en) | 2007-08-23 | 2008-07-23 | Aqueous pigment preparations comprising anionic additives based on allyl ether and vinyl ether |
| JP2010521328A JP5358575B2 (ja) | 2007-08-23 | 2008-07-23 | アリル−及びビニルエーテルに基づくアニオン性添加剤を含む水性顔料調合物 |
| EP08784979A EP2183327B8 (de) | 2007-08-23 | 2008-07-23 | Wässrige pigmentpräparationen mit anionischen additiven auf allyl- und vinyletherbasis |
| KR1020107003859A KR101503951B1 (ko) | 2007-08-23 | 2008-07-23 | 알릴 에터 및 비닐 에터에 기초한 음이온성 첨가제를 포함하는 수성 안료 제제 |
| CN2008800200602A CN101679795B (zh) | 2007-08-23 | 2008-07-23 | 含基于烯丙基醚和乙烯基醚的阴离子添加剂的水性颜料制剂 |
| DE502008001965T DE502008001965D1 (de) | 2007-08-23 | 2008-07-23 | Wässrige pigmentpräparationen mit anionischen additiven auf allyl- und vinyletherbasis |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007039783A DE102007039783A1 (de) | 2007-08-23 | 2007-08-23 | Wässrige Pigmentpräparationen mit anionischen Additiven auf Allyl- und Vinyletherbasis |
| DE102007039783.8 | 2007-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009024232A1 true WO2009024232A1 (de) | 2009-02-26 |
Family
ID=40184994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2008/006020 Ceased WO2009024232A1 (de) | 2007-08-23 | 2008-07-23 | Wässrige pigmentpräparationen mit anionischen additiven auf allyl- und vinyletherbasis |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8202361B2 (https=) |
| EP (1) | EP2183327B8 (https=) |
| JP (1) | JP5358575B2 (https=) |
| KR (1) | KR101503951B1 (https=) |
| CN (1) | CN101679795B (https=) |
| DE (2) | DE102007039783A1 (https=) |
| ES (1) | ES2353361T3 (https=) |
| WO (1) | WO2009024232A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007021867A1 (de) | 2007-05-10 | 2008-11-20 | Clariant International Limited | Pigmentpräparationen auf Wasserbasis |
| DE102007021868A1 (de) * | 2007-05-10 | 2008-11-20 | Clariant International Limited | Nichtionische wasserlösliche Additive |
| DE102007021869A1 (de) * | 2007-05-10 | 2008-11-13 | Clariant International Limited | Anionische wasserlösliche Additive |
| DE102007039784A1 (de) * | 2007-08-23 | 2009-02-26 | Clariant International Limited | Anionische wasserlösliche Additive auf Allyl- und Vinyletherbasis |
| DE102007039781A1 (de) * | 2007-08-23 | 2009-02-26 | Clariant International Ltd. | Wässrige Pigmentpräparationen mit nichtionischen Additiven auf Allyl- und Vinyletherbasis |
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| FR2982266B1 (fr) * | 2011-11-04 | 2015-02-20 | Coatex Sas | Emulsion d'un polymere acrylique associatif polymerise en presence de polyglycerols et son utilisation comme agent epaississant dans une formulation aqueuse. |
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| FR3003264B1 (fr) | 2013-03-18 | 2016-12-09 | Coatex Sas | Utilisation d'une emulsion polymerique pour traiter en surface des particules de matiere minerale. |
| CN103710772B (zh) * | 2013-12-30 | 2015-09-23 | 苏州世名科技股份有限公司 | 纤维原液着色用超细炭黑水性色浆 |
| JP6310375B2 (ja) * | 2014-09-29 | 2018-04-11 | 富士フイルム株式会社 | 水性インク組成物 |
| US9718737B2 (en) | 2015-04-21 | 2017-08-01 | Behr Process Corporation | Decorative coating compositions |
| IT201800005349A1 (it) * | 2018-05-14 | 2019-11-14 | Sospensione per inchiostri per stampa digitale | |
| CN109776739B (zh) * | 2018-12-29 | 2021-09-14 | 广州星业科技股份有限公司 | 一种高分子防串色助洗剂 |
| CN111117371B (zh) * | 2020-01-20 | 2022-05-06 | 浙江纳美新材料股份有限公司 | 一种竹木染色专用色浆及其制备方法 |
| CN111268842B (zh) * | 2020-02-25 | 2022-05-20 | 濮阳市盛源能源科技股份有限公司 | 一种污水处理方法 |
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-
2008
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- 2008-07-23 CN CN2008800200602A patent/CN101679795B/zh not_active Expired - Fee Related
- 2008-07-23 DE DE502008001965T patent/DE502008001965D1/de active Active
- 2008-07-23 JP JP2010521328A patent/JP5358575B2/ja not_active Expired - Fee Related
- 2008-07-23 ES ES08784979T patent/ES2353361T3/es active Active
- 2008-07-23 EP EP08784979A patent/EP2183327B8/de not_active Not-in-force
- 2008-07-23 US US12/674,137 patent/US8202361B2/en not_active Expired - Fee Related
- 2008-07-23 KR KR1020107003859A patent/KR101503951B1/ko not_active Expired - Fee Related
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| EP1142972A2 (de) * | 2000-04-08 | 2001-10-10 | Goldschmidt AG | Dispergiermittel zur Herstellung wässriger Pigmentpasten |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101679795B (zh) | 2012-04-18 |
| JP5358575B2 (ja) | 2013-12-04 |
| KR101503951B1 (ko) | 2015-03-18 |
| DE102007039783A1 (de) | 2009-02-26 |
| DE502008001965D1 (de) | 2011-01-13 |
| US20110107803A1 (en) | 2011-05-12 |
| ES2353361T3 (es) | 2011-03-01 |
| KR20100065281A (ko) | 2010-06-16 |
| EP2183327B1 (de) | 2010-12-01 |
| EP2183327A1 (de) | 2010-05-12 |
| EP2183327B8 (de) | 2011-02-16 |
| JP2010536961A (ja) | 2010-12-02 |
| CN101679795A (zh) | 2010-03-24 |
| US8202361B2 (en) | 2012-06-19 |
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