Classifications

• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions

Definitions

• the present invention relates to pigment preparation based on
• Benzimidazolone dioxazine pigment (CI Pigment Blue 80) and a specific dispersant based on a substituted pigment violet 23.
• the pigment preparation according to the invention can be used in highly polar aqueous polyurethane-based paints and in high-solids, low-solvent acrylic resin paints. Also suitable are coating systems from the class of alkyd melamine resin lacquers and two-component lacquers based on polyisocyanate-crosslinkable acrylic resins. Further fields of application are effect paints in the automotive sector, industrial coatings, in particular color filters, ink jet inks, electrophotographic toners and developers, and e-inks.
• Pigment preparations are combinations of base pigments and pigment dispersants, which are pigments substituted with groups having specific activity.
• the pigment dispersants are added to the pigments in order to facilitate the dispersion in the application media, in particular for paints, printing inks and color filters, and to improve the theological and coloristic properties of the pigments.
• the viscosity of the highly pigmented color concentrates (Millbase) is lowered and the flocculation of the pigment particles is reduced. As a result, for example, the color strength, the transparency and the gloss can be increased. This is particularly desirable for metallic paints and color filters.
• color filters With color filters, a full-color image is created using transmitted light from red, green and blue pixels.
• AM active matrix
• PM passive matrix
• Coior filters In the color filters, a distinction is made between AM (active matrix) and PM (passive matrix) LCD (iiquid crystal dispay) Coior filters, whereby the TFT (thin-fum transistor) LCD color filters are of particular importance.
• Color filter displays are used in a variety of electro-optical systems, such. in screens of desktop monitors, in computer screens, portable computer screens (laptops, portable computers), personal digital assistants (PDAs), and mobile phones,
• Video camera GPS (global positioning systems) and other monitors, and in general in liquid crystal and charge-coupled devices, plasma displays or in electroluminescent and other displays.
• the latter can e.g. active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or e.g. Light-emitting diodes.
• color filters are used in Fiat Panel Displays, which are increasingly replacing conventional cathode ray television screens, or which can generally be used as a display panel of any size for still and moving information.
• a typical LCD color filter construction can be described schematically as follows: Between two glass plates there is a thin layer of liquid crystals.
• the upper glass plate has next to a number of other functional components on the outer surface of the corresponding pixels, for example, red, green, blue (R 1 G 1 B). These pixels are outlined in black for a better contrast, to the outside the R, G, B pixels are protected by a suitable protective layer against environmental influences, such as scratches.
• the lower glass plate contains other functional components such as ITO (Indium Tin Oxide) and TFT (Thin Film Transistors), which among other things serve to drive the individual pixels.
• the liquid crystal can pass through be set to "light” or “dark” electronic control (or any intermediate level).
• the color filter pixels are supplied with light and to the human eye results in a corresponding R, G, B building, colored, moving or still image.
• Pigment preparation for up to 1 hour temperatures up to 300 0 C must endure; good dispersibility in color filter systems; - steep and narrow absorption bands of each applied color filter
• the known pigments and pigment preparations do not always meet all the requirements of the art. In particular for blue pigments, there was a need to improve the color strength, color purity, transparency, rheology and gloss.
• the aim of the present invention was to provide a highly transparent colorant having a reddish baud tone, in particular for the use of effect paints in the automotive industry and industrial paints, color filters, ink jet inks, electrophotographic toners and developers and e-inks.
• the object has surprisingly been achieved by the following pigment preparation.
• the present invention is a pigment preparation, characterized by a content of a) a BenzimidazolondioxazinENS of formula (I) as a base pigment
• Q is an m-valent radical of a compound of the formula (III),
• n is a number from 1 to 4, preferably 1 to 3, in particular 1 to 2, is.
• the pigment preparation according to the invention expediently contains 0.5 to 99% by weight, preferably 1 to 75% by weight, in particular 2.5 to 50% by weight, very particularly preferably 5 to 30% by weight, of pigment dispersant of the formula (IV), based on the weight of the base pigment of the formula (I).
• the pigment of formula (I) is as Cl. Pigment Blue 80 known
• the invention also provides a process for the preparation of a pigment preparation according to the invention, characterized in that the
• the pigment preparation is preferably prepared by grinding the components in dry form, in moist form or in suspension.
• Pigment dispersant to Benzimidazolondioxazinpigment during milling or just before a finish.
• a third preparation variant is mixing in dry form before pulverization.
• the dry components may be in granular or powder form mixed before or after grinding; one component may be added to the other component in wet or dry form, for example by mixing the components in the form of the wet presscake.
• the mixing can be carried out, for example, by milling in dry form, in moist form, for example by kneading, or in suspension, or by a combination of these processes.
• the grinding can be carried out with the addition of water, solvents, alkalis or grinding aids such as salt. Particularly preferred is the bead milling at a pH between 7.0 and 12.0.
• the benzimidazolone dioxazine crude pigment usually obtained in the course of chemical synthesis is crushed, for example by dry or wet grinding.
• the resulting finely crystalline benzimidazolone dioxazines are subjected to an after-treatment, generally referred to as finish, for example in water and / or solvents and usually at elevated temperature, for example up to 200 ° C., and optionally elevated pressure.
• finish for example in water and / or solvents and usually at elevated temperature, for example up to 200 ° C., and optionally elevated pressure.
• elevated temperature for example up to 200 ° C.
• the pigment dispersant can also be added in partial portions at different times.
• the pigment preparation according to the invention can be used as preferably aqueous presscake or wet granules, but as a rule they are solid systems of free-flowing, powdery nature or granules.
• drying units In the drying of a wet pigment preparation, the known drying units can be used, such as drying cabinets,
• Paddle wheel dryers tumble dryers, contact dryers and in particular spinflash and spray dryers.
• a suitable drying unit low-dust and free-flowing powder or granules can be produced.
• the pigment preparations according to the invention may contain, in addition to the benzimidazolone dioxazine pigment and the pigment dispersant, further customary auxiliaries or additives, for example surfactants, nonpigmentary and pigmentary dispersants, fillers, extenders, resins, waxes, defoamers, antifoggants, extenders, antistatic agents, colorants for shading, for example PV 23, preservatives, drying retardants, rheology control additives, wetting agents, antioxidants, biocides, UV absorbers and light stabilizers , preferably in an amount of 0.1 to 60 wt .-%, in particular 0.5 to 35 wt .-%, based on the total weight of the pigment preparation.
• auxiliaries or additives for example surfactants, nonpigmentary and pigmentary dispersants, fillers, extenders, resins, waxes, defoamers, antifoggants, extenders, antistatic agents, colorants for shading, for example PV 23, preservative
• Suitable surfactants are anionic or anionic, cationic or cationic and nonionic or amphoteric substances or mixtures of these agents.
• Anionic substances for example, fatty acid taurides, fatty acid N-methyltaurides, fatty acid isethionates, alkylphenyl, such as dodecylbenzenesulfonic acid, alkylnaphthalenesulfonates, alkylphenol polyglycol ether sulfates, fatty alcohol polyglycol ether, fatty acid amide polyglycol ether sulfates, alkyl sulfosuccinamates, alkenylsuccinic, Fettalkoholpolyglykol-ethersulfosuccinate, alkane sulfonates, fatty acid glutamates, alkyl sulfosuccinates, fatty acid sarcosides; Fatty acids, for example palmitic, stearic and oleic acids; the salts of these anionic substances and soaps, for example alkali metal salts of fatty acids, naphthenic acids and resin acids, for
• cation-active substances are, for example, quaternary ammonium salts, Fettaminoxalkylate, polyoxyalkyleneamines, alkoxylated polyamines, Fettaminpolyglykolether, primary, secondary or tertiary amines, for example alkyl, cycloalkyl or cyclized alkylamines, especially fatty amines derived from fatty amines or fatty alcohols di- and polyamines and their alkoxylates of Fatty acid derived imidazolines, polyaminoamido or Polyamino compounds or resins having an amine index between 100 and 800 mg KOH per gram of Poiyaminoamido- or Poiyaminoharm, and salts of these cationic substances, such as acetates or chlorides into consideration.
• Suitable nonionic and amphoteric substances are, for example, fatty amine carboxyglycinates, amine oxides, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, betaines such as fatty acid amide N-propyl betaines, phosphoric esters of aliphatic and aromatic alcohols, fatty alcohols or fatty alcohol polyglycol ethers, fatty acid amide ethoxylates, fatty alcohol alkylene oxide adducts and alkylphenol polyglycol ethers.
• nonpigmentary dispersants substances which are not structurally derived from organic pigments. They are added as dispersants either already in the production of pigments, but often also during the incorporation of the pigments into the application media to be dyed, for example in the production of paints or printing inks by dispersing the pigments in the corresponding binders.
• They may be polymeric substances, for example polyolefins, polyesters, polyethers, polyamides, polyimines, polyacrylates, polyisocyanates, block copolymers thereof, copolymers of the corresponding monomers or polymers of one class modified with a few monomers of a different class. These polymeric substances carry polar anchor groups such as, for example, hydroxy, amino, imino and ammonium groups, carboxylic acid and carboxylate groups, sulfonic acid and sulfonate groups or phosphonic acid and
• Nonpigmentary dispersants may also be chemically functional group modified aromatic non-organic pigment derived substances.
• Nonpigmentary dispersants are known in the art and some are available commercially (for example, Solsperse ®, Avecia; Disperbyk ®, Byk-Chemie, Efka ®, Efka).
• any other substances described can be used, for example, condensation products of isocyanates and alcohols, diols or polyols, amino alcohols or di- or polyamines, polymers of hydroxycarboxylic acids, copolymers of olefin monomers or vinyl monomers and ethylenically unsaturated carboxylic acids and esters, urethane-containing polymers of ethylenically unsaturated monomers, urethane-modified polyesters, condensation products based on Cyanuric halides, nitroxyl-containing polymers, polyesteramides, modified polyamides, modified acrylic polymers, comb-like dispersants of polyester and acrylic polymers, phosphoric acid esters, triazine-derived polymers, modified polyethers or dispersants derived from aromatic non-pigmentary substances.
• These basic structures are often further modified, for example by chemical reaction with other functional groups bearing substances or by salt formation.
• Anionic groups of the nonpigmentary and pigmentary dispersants, surfactants or resins used as auxiliaries can also be laked, for example by Ca, Mg, Ba, Sr, Mn or Al ions or by quaternary ammonium ions.
• fillers or extenders is meant a plurality of substances according to DIN 55943 and DIN EN 971-1, for example the various types of talc, kaolin, mica, dolomite, lime, barium sulfate or titanium dioxide. In this case, the addition has proven especially before the pulverization of the dried pigment preparation.
• the invention also relates to the use of the pigment preparation of the invention for pigmenting high molecular weight organic materials, for example plastics, resins, paints, powder coatings, paints, electret materials, printing inks and seeds, but especially for effect finishes, automotive coatings, industrial coatings, color filters, ink jet inks , electrophotographic toners and developers and e-inks.
• organic materials for example plastics, resins, paints, powder coatings, paints, electret materials, printing inks and seeds, but especially for effect finishes, automotive coatings, industrial coatings, color filters, ink jet inks , electrophotographic toners and developers and e-inks.
• cellulose compounds such as cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetates or cellulose butyrates, natural binders such as fatty acids, fatty oils, resins and their conversion products, or synthetic resins such as polycondensates, polyadducts,
• Polymers and copolymers such as aminoplasts, in particular urea and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins and phenolic resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl acetates or polyvinyl ethers, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene or polypropylene, poly (meth) acrylates and their copolymers, such as polyacrylic acid esters or polyacrylonitriles, polyamides, polyesters, polyurethanes, coumarone-indene and hydrocarbon resins, epoxy resins, unsaturated synthetic resins (polyesters, acrylates) with the different hardening mechanisms, waxes, aldehyde and ketone resins , Rubber, rubber and
• the present invention therefore also relates to a high molecular weight organic material containing a dyeing effective amount of a pigment preparation according to the invention.
• the pigment preparation according to the invention is usually used in an amount of from 0.01 to 30% by weight, preferably from 0.1 to 15% by weight.
• the reddish-blue shades of the pigment preparations according to the invention are particularly well suited for the color filter red-green-blue color set (R, G, B).
• Typical colorants for the red color point are pyrrolopyrrole, quinacridone and azo pigments, such as PR 254, PR 209, PR175 and PO 38, alone or mixed.
• phthalocyanine colorants are typically used, such as PG36 and PG7. If necessary, the colors can be added to other colors
• Nuancieren be mixed.
• red and green hue is preferably blended with yellow, for example with P.Y. 138,139,150,151, 180 and 213.
• the pigment preparation according to the invention is distinguished by its excellent coloristic and rheological properties, in particular high flocculation stability, easy dispersibility, good rheology, high color strength, transparency and saturation (chroma). They are easy to disperse in many application media and to high levels of fineness. Other properties, such as gloss, overcoating fastness, solvent fastness, acid fastness, light and weather fastness and high purity of hue, are very good.
• hues in the reddish-blue range which are required when used in color filters can be achieved. Here, they ensure high contrast and also meet the other requirements for use in color filters, such as high temperature stability or steep and narrow ones
• Absorption bands They can be produced with high purity and low levels of ions.
• the color filters can be produced by customary processes.
• the pigment preparation according to the invention is dispersed in an aqueous or nonaqueous system which may also contain further components, such as, for example, binders.
• Binders may be thermoplastic, thermosetting or photosensitive. Examples of thermoplastic and thermosetting binders include acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins. Photosensitive binders are known per se.
• the color filter paste thus prepared has a concentration of pigment preparation of 2.5 to 80 wt .-%.
• These dispersions can then by spin coating or suitable conventional printing methods (eg, flexographic, offset, screen, intagiio and stamp printing) or non-contact printing methods (eg ink jet) on the Color Filter carrier material, typically a Glass plate to be applied.
• suitable conventional printing methods eg, flexographic, offset, screen, intagiio and stamp printing
• non-contact printing methods eg ink jet
• the pixels can also be generated by thermal sublimation, thermal transfer, electrodeposition, or other suitable application method.
• the typical use concentration of the pigment preparations of the invention in the applied color filter film is between 5 and 95 wt .-%, preferably between 20 and 80 wt .-%, most preferably between 40 and 60 wt .-%, based on the total weight of the color filter film.
• the most commonly used method is spincoating.
• the pixels e.g. R, G, B applied.
• An applied photoresist layer is e.g. Radiation exposed, then developed so that only individual pixels of the colored layer remain.
• solvents preferably organic solvents
• all polar or non-polar organic solvents which, depending on the application method, have to fulfill other properties such as water compatibility or intolerance, temperature stability or safety and ecotox-relevant aspects, are suitable in principle.
• Typical solvents are ethylcellosolve acetate, diethylene glycol alkyl ethers (eg diethylene glycol monoethyl ether, diethylene glycol dimethyl ether), propylene glycol alkyl ether acetates (eg propylene glycol monomethyl ether acetate), ethylene glycol alkyl ether acetates (eg ethylene glycol monoethyl ether acetate), N-methylpyrrolidone, ketones (eg methyl ethyl ketones, cyclohexanone and cyclopentanone), alcohols, aromatic hydrocarbons, esters ( eg ethyl 3-ethoxypropionate), cyclic esters. These solvents can be used individually or in combination with each other.
• diethylene glycol alkyl ethers eg diethylene glycol monoethyl ether, diethylene glycol dimethyl ether
• propylene glycol alkyl ether acetates eg prop
• the pigment preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners.
• Toner particles may also be used for cosmetic and pharmaceutical applications, e.g. for coating tablets.
• Typical toner binders are polymerization, polyaddition and
• Polycondensation resins such as styrene, styrene acrylate, styrene butadiene, acrylate, polyester, phenolic epoxy resins, polysulfones, polyurethanes, individually or in combination, as well as polyethylene and polypropylene, which may contain other ingredients, such as charge control agents, waxes or flow aids or be modified afterwards with these additions.
• Electrophotographic toners or developers contain a conventional toner binder and between 0.1 and 80 wt .-%, preferably between 1 and 40 wt .-% and particularly preferably between 3 and 20 wt .-% of a pigment preparation of the invention and between 0 and 20 wt.
• a charge control agent from the class of triphenylmethanes, ammonium and ImmoniumENSen; fluorinated ammonium and immonium compounds; biscationic acid amides; polymeric ammonium compounds; Diallylammonium compounds, arylsulfide derivatives, phenol derivatives, phosphonium compounds, and fluorinated phosphonium compounds; Calix (n) arenes; cyclodextrins; Polyester salts; Metal complex compounds; Cyclooligosaccharide boron complexes, inter-polyelectrolyte complexes; benzoimidazolones; Azines, thiazines or oxazines.
• Electrophotographic toners may still contain waxes. Furthermore, waxes can also be used as a predispersed concentrate, it being possible for the concentrates (masterbatch) to be multicomponent: Component are the colorants, resins, charge control agents and combinations thereof according to the invention.
• pigment preparations according to the invention are suitable as colorants in ink-jet inks on aqueous and non-aqueous basis, in
• Microemulsion inks and in such inks that work by the hot-melt method are Microemulsion inks and in such inks that work by the hot-melt method.
• Ink-jet inks generally contain a total of 0.5 to 25 wt .-%, preferably 1, 5 to 8 wt .-%, (calculated dry) of a pigment preparation according to the invention.
• Microemulsion inks are based on organic solvents, water and optionally an additional hydrotropic substance (interface mediator).
• Microemulsion inks generally contain from 0.5 to 15% by weight, preferably from 1.5 to 8% by weight, of a pigment preparation according to the invention, from 5 to 99% by weight of water and from 0.5 to 94.5% by weight of organic Solvent and / or hydrotrope.
• solvent based ink jet inks preferably contain 0.5 to 15% by weight of a pigment preparation according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds.
• Hot-melt inks are usually based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and liquid when heated, the preferred melting range between about 60 0 C and 140 0 C is about.
• hot-melt ink-jet inks consist essentially of 20 to 90% by weight of wax and 1 to 10% by weight of an inventive composition
• Pigment preparation Furthermore, 0 to 20 wt .-% of an additional polymer (as a "dye remover"), 0 to 5 wt .-% dispersing aid, 0 to 20 wt .-% viscosity modifier, 0 to 20 wt .-% plasticizer, 0 to 10 wt % Of tackiness additive, 0 to 10% by weight of transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight of antioxidant.
• an additional polymer as a "dye remover”
• dispersing aid 0 to 20 wt .-% viscosity modifier
• plasticizer 0 to 20 wt .-% plasticizer
• 0 to 10 wt % Of tackiness additive 0 to 10% by weight of transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight of antioxidant.
• the pigment preparations according to the invention are also suitable as colorants for electronic inks ("electronic inks” or “e-inks”) or "electronic paper”("e-paper”).
• electronic inks electronic inks
• e-inks electronic inks
• e-paper electronic paper
• effect coatings This effect is created by pissentisch-shaped metaiischen or mineral pigments and is characterized by a viewing angle dependent brightness or color impression.
• effect pigments it makes sense to select those organic pigments that do not interfere with the metallic effect.
• transparent pigments are the first to be used, which scatter the light only slightly: the more transparent the organic pigment, the more pronounced is the angle-dependent effect of the effect pigments in a coating.
• the particle size distribution of the pigment preparation according to the invention is very narrow-band, which is an important criterion for suitability in color filters.
• a measure of the narrowbandness of the particle size distribution are the
• pigment preparations having dgs are smaller than
• nm in particular less than 100 nm, with d 50 smaller than 100 nm, in particular smaller than 50 nm, and with d 2 5 smaller than 80 nm, in particular smaller than 45 nm.
• wet grinding can be combined on a bead mill with an upstream grinding, this upstream grinding is preferably a dry grinding, eg on a vibrating mill.
• the blue pigment preparation according to the invention can be used individually or in
• pigment preparations serve either as shading colorants which can be added in amounts of from 1% to 49% by weight, e.g. when nuancing Pigment Blue 15, or the. Pigment preparations are the main components.
• surface-modified pigments whose surface has been modified by chemical processes such as, for example, sulfonation or diazotization and provided with functional, optionally charge-carrying groups or polymer chains (referred to in the English literature as self-dispersing or graft pigments) are also suitable.
• suitable inorganic pigments are titanium dioxides, zinc sulfides, iron oxides, chromium oxides, ultramarine, nickel or chromium antimony titanium oxides, cobalt oxides and bismuth vanadates.
• Suitable organic dyes are preferably solvent-soluble dyes, such as solvent dyestuffs and fatty dyes, but also acid dyes, direct dyes, sulfur dyes and their leuco form, metal complex dyes or reactive dyes, wherein in the case of reactive dyes also reacted with nucleophiles dyes can be used.
• solvent-soluble dyes such as solvent dyestuffs and fatty dyes, but also acid dyes, direct dyes, sulfur dyes and their leuco form, metal complex dyes or reactive dyes, wherein in the case of reactive dyes also reacted with nucleophiles dyes can be used.
• organic pigments are carbon black pigments, such as gas or Furnaceruße; Monoazo and disazo pigments, in particular the Color Index pigments, individually or in combination, such as: Pigment Red 2, Pigment Red 3, Pigment Red 4, Pigment Red 5, Pigment Red 9, Pigment Red 12, Pigment Red 14, Pigment Red 38 Pigment Red 48: 2, Pigment Red 48: 3, Pigment Red 48: 4, Pigment Red 53: 1, Pigment Red 57: 1, Pigment Red 112, Pigment Red 122, Pigment Red 144, Pigment Red 146, Pigment Red 147 Pigment Red 169, Pigment Red 168, Pigment Red 169, Pigment Red 170, Pigment Red 175, Pigment Red 176, Pigment Red 177, Pigment Red 179, Pigment Red 181, Pigment Red 184, Pigment Red 185, Pigment Red 187, Pigment Pigment Red 207, Pigment Red 208, Pigment Red 208, Pigment Red 209, Pigment Red 210, Pigment Red 214, Pigment Red 242,
• Pigment Orange 5 Pigment Orange 13, Pigment Orange 34, Pigment Orange 36, Pigment Orange 38, Pigment Orange 43, Pigment Orange 62, Pigment Orange 68, Pigment Orange 70, Pigment Orange 72 or Pigment Orange 74; Pigment Green 7 or Pigment Green 36 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 Blue 56, Pigment Blue 60 or Pigment Blue 61.
• the pigment preparations according to the invention are preferably used for shading green, blue and red pigments. Particularly preferred are combinations of the pigment preparation according to the invention with Cl. Pigment Blue 15: 6 and / or with Cl. Pigment Violet 23.
• the pigment preparation according to the invention is highly transparent, has excellent weatherfastness even in low concentrations and has a sufficiently high tinting strength.
• an alkyd-melamine resin paint based on a medium-oil alkyd resin and a butanolveretherten melamine resin (AM) and a high-solid Acrylharzeinbrennlack based on a non-aqueous Suspension (HSS) and a highly polar, aqueous polyurethane varnish (WBL) selected.
• AM butanolveretherten melamine resin
• HSS non-aqueous Suspension
• WBL highly polar, aqueous polyurethane varnish
• the coloristic properties were determined according to DIN 55986.
• the rheology of the millbase after dispersion was assessed visually using the following five-step scale.
• the viscosity was determined after diluting the millbase to the final pigment concentration with the Rossmann viscospatula, type 301 from Erichsen.
• Comparative Example A 400 parts of crude pigment (Pigment Blue 80) in 4 liters of water are placed in a stirred original. This suspension is packed in a stirred ball mill of the type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts of zirconium mixed oxide beads of diameter 0.3 to 0.4 mm as grinding media, with a peripheral speed of 11.8 m / s and a specific power density of 2.0 kW per liter grinding room is operated, milled to a residence time of 20 minutes at 20 ° C. To 200 parts of the grinding suspension is added 143 parts of isobutanol. After several hours of stirring at the boiling point of the alcohol is through
• Example 1 348 parts of crude pigment (Pigment Blue 80) and 52 parts of the pigment dispersant (IV) with m equal to 1 in 4 liters of water are placed in a stirred original.
• This suspension is packed in a stirred ball mill of the type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts of zirconium mixed oxide beads of diameter 0.3 to 0.4 mm as grinding media, with a peripheral speed of 11.8 m / s and a specific power density of 2.0 kW per liter grinding chamber is operated, milled to a residence time of 15 minutes at 20 to 50 0 C. To 200 parts of the grinding suspension is added 143 parts of isobutanol.
• Agitator ball mill type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts zirconium mixed oxide beads diameter from 0.3 to 0.4 mm as a grinding body, with a peripheral speed of 11, 8 m / s and a specific power density of 2.0 kW per liter of grinding room, milled to a residence time of 15 minutes at 20 to 50 0 C.
• This suspension is packed in a stirred ball mill of the type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts of zirconium mixed oxide beads of diameter 0.3-0.4 mm as grinding media, with a peripheral speed of 11.8 m / s and a specific power density of 2.0 kW per liter grinding chamber is operated, milled to a residence time of 15 minutes at 20 to 50 0 C. To 200 parts of the grinding suspension is added 143 parts of isobutanol. After several hours of stirring at the boiling point of the alcohol is through
• This suspension is packed in a stirred ball mill of the type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts of zirconium mixed oxide beads of diameter 0.3-0.4 mm as grinding media, with a peripheral speed of 11.8 m / s and a specific power density of 2.0 kW per liter grinding chamber is operated, milled to a residence time of 15 minutes at 20 to 50 0 C. To 200 parts of the grinding suspension is added 0.9 parts of a condensation product based on cyanuric chloride, taurine, N.N'-diethylaminopropylamine and p-phenylenediamine and 143 parts of isobutanol. After stirring for several hours at the boiling point, the alcohol is removed by steam distillation, with formic acid to pH 4, the
• Example 8 27 parts of crude coarse pigment (Pigment Blue 80) and 3 parts
• Pigment dispersant (IV) with m equal to 1 are introduced into a cylindrical 1 liter plastic vessel which is filled with 1400 parts of Cylpebs (from corundum, of 12 ° mm diameter, manufacturer: general GmbH, Hof) as grinding media. The mixture is then for 8 hours while shaking on an oscillating mill: mm at 1400 revolutions per minute, oscillating circuit 4, finely ground (type Vibratom ® manufacturer Siebtechnik Mühlheim). Thereafter, the millbase is screened off from the grinding media. This gives 29 parts of ground material. To 40.5 parts of the millbase is added 350 parts of isobutanol.
• This suspension is packed in a stirred ball mill of the type Drais DCP SF 12 (manufacturer: Draiswerke GmbH, Mannheim), which is filled with 2200 parts of zirconium mixed oxide beads of diameter 0.3 to 0.4 mm as grinding media, with a peripheral speed of 11.8 m / s and a specific power density of 2.0 kW per liter grinding chamber is operated, milled to a residence time of 15 minutes at 20 to 50 ° C. To 200 parts of the grinding suspension is added 143 parts of isobutanol. After several hours of stirring at the boiling point, the alcohol is removed by steam distillation, the suspension is filtered off with suction, washed the presscake and dried at 80 0 C. There are obtained 17.2 parts of pigment preparation.
• the pigment preparation is ground over a pin mill.
• a well-crystalline powder is obtained which, when tested in HSS varnish, gives very pure, strong, full-shade transparent varnishes.
• the rheology of the paint is rated grade 5.

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• Organic Chemistry (AREA)
• Paints Or Removers (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Pigments, Carbon Blacks, Or Wood Stains (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

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• 2005
  • 2005-05-31 DE DE102005024722A patent/DE102005024722A1/de not_active Withdrawn
• 2006
  • 2006-04-29 CN CNA2006800228863A patent/CN101208393A/zh active Pending
  • 2006-04-29 JP JP2008513956A patent/JP2008542482A/ja not_active Ceased
  • 2006-04-29 KR KR1020077027832A patent/KR20080012322A/ko not_active Withdrawn
  • 2006-04-29 DE DE502006003329T patent/DE502006003329D1/de active Active
  • 2006-04-29 CA CA002610174A patent/CA2610174A1/en not_active Abandoned
  • 2006-04-29 US US11/921,550 patent/US7686883B2/en not_active Expired - Fee Related
  • 2006-04-29 WO PCT/EP2006/004055 patent/WO2006128539A2/de not_active Ceased
  • 2006-04-29 EP EP06753464A patent/EP1891163B1/de not_active Not-in-force
  • 2006-04-29 BR BRPI0611212-9A patent/BRPI0611212A2/pt not_active IP Right Cessation
  • 2006-04-29 ES ES06753464T patent/ES2321978T3/es active Active

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