WO2008107075A2 - Préparations pigmentaires à base de dicétopyrrolopyrroles - Google Patents

Préparations pigmentaires à base de dicétopyrrolopyrroles Download PDF

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Publication number
WO2008107075A2
WO2008107075A2 PCT/EP2008/001308 EP2008001308W WO2008107075A2 WO 2008107075 A2 WO2008107075 A2 WO 2008107075A2 EP 2008001308 W EP2008001308 W EP 2008001308W WO 2008107075 A2 WO2008107075 A2 WO 2008107075A2
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WO
WIPO (PCT)
Prior art keywords
pigment
red
preparation according
pigment preparation
formula
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PCT/EP2008/001308
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German (de)
English (en)
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WO2008107075A3 (fr
Inventor
Matthias Ganschow
Carsten Plüg
Tanja Reipen
Klaus Mikulecky
Marcus Paczkowski
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Clariant Finance (Bvi) Limited
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Publication of WO2008107075A2 publication Critical patent/WO2008107075A2/fr
Publication of WO2008107075A3 publication Critical patent/WO2008107075A3/fr

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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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0039—Mixtures of diketopyrrolopyrroles
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0022—Wet grinding of pigments
    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/322—Pigment inks
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/36—Pearl essence, e.g. coatings containing platelet-like pigments for pearl lustre
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes

Definitions

  • the present invention relates to novel pigment preparations with Cl. Pigment Red 254 as the base pigment and certain anionic pigment dispersants.
  • Pigment preparations are combinations of base pigments and so-called pigment dispersants, which are pigments substituted with groups having specific activity.
  • the pigment dispersants are added to the pigments to facilitate dispersion in the application media, particularly in paints, inks and inks, and to improve the theological and coloristic properties of the pigments. As a result, for example, the color strength, the transparency and the gloss can be increased in many applications.
  • WO 01/04215 discloses a finely divided diketopyrrolopyrrole pigment, Cl. Pigment Red 254 (I),
  • Cl. Pigment Red 254 can be obtained by subjecting a crude pigment initially stirred with an inorganic salt dry at least 80 0 C, and then a kneading process with inorganic salts in the presence of organic solvents is exposed.
  • EP-A-1 104 789 describes pigment dispersants based on pigments, e.g. of diketopyrrolopyrroles or quinacridones.
  • Pigment Red 254 As base pigment to provide the high color strength, low viscosity and the lowest possible color shade deviation from the base pigment Cl. Pigment Red 254 and are particularly suitable for color filter applications.
  • the invention provides pigment preparations characterized by a content of Cl. Pigment Red 254 of 20 to 100 nm, and a pigment dispersant of the formula with an average particle size d 5 o (II)
  • Q is a residue of an organic pigment from the group Cl. Pigment Red 264 and Cl. Pigment Violet 19 is; s represents a number from 1 to 5; n represents a number from 0 to 4; wherein the sum of s and n is 1 to 5;
  • R 1 is a bivalent branched or unbranched, saturated or unsaturated, aliphatic hydrocarbon radical having 1 to 20 C atoms, or a C 5 -C 7 cycloalkylene radical, or a bivalent aromatic radical having 1, 2 or 3, preferably 1 or 2 aromatic rings wherein the rings may be condensed or linked by a bond, such as a phenyl, biphenyl or naphthyl radical, or a bivalent heterocyclic radical having 1, 2 or 3 rings, 1, 2, 3 or
  • Number is from 1 to 30 and the two radicals R 80 are independent of each other
  • R 9 , R 10 , R 11 and / or R 12 may be substituted alkyl, alkenyl, cycloalkyl, phenyl or alkylphenyl by amino, hydroxy, and / or carboxy; or wherein the substituents R 9 and R 10 together with the quaternary nitrogen atom is a five- to seven-membered saturated ring system, which may be further
  • Heteroatoms from the group O, S and N contains, for example, pyrrolidone, imidazolidine, hexamethyleneimine, piperidine-piperazine or
  • N-atom a five- to seven-membered aromatic ring system, which optionally contains even more heteroatoms from the group O, S and N and on which optionally additional rings are fused, can form, for example, the pyrrole,
  • R 15 , R 16 , R 17 and R 18 are independently hydrogen or a
  • T is a branched or unbranched C 2 -C 6 -alkylene radical; or wherein T, when q> 1, may also be a combination of branched or unbranched C 2 -C 6 -alkylene radicals.
  • pigment dispersants of the formula (II) in which R 1 is a branched or unbranched C 1 -C 10 -alkylene group, in particular ethylene, propylene or butylene, or a phenylene radical.
  • E + and G + denote the corresponding stoichiometric equivalent of Ca 2+ , Sr 2+ , Ba 2+ or Al 3+ .
  • the pigment dispersants of formula (II) are compounds known per se and can be prepared by known methods, e.g. according to EP-B1-1 362 081.
  • the weight ratio of Cl. Pigment Red 254 to pigment dispersant of the formula (II) preferably between (99.9 to 0.1) and (80 to 20), particularly preferably between (99 to 1) and (83 to 17), in particular between (97 to 3) and (85 to 15), and most preferably between (95 to 5) and (87 to 13).
  • Chroma (C) is the parameter that describes the chroma of the color at given brightness
  • ⁇ C describes the difference in chroma of two colors
  • ⁇ H describes the difference in hue for two colors to be compared.
  • Pigment Red 254 and the same particle size has a ⁇ H (after CIELAB) of preferably not more than 2.0, in particular not more than 1, 5 and particularly preferably not more than 1, 0.
  • the ⁇ C (after CIELAB) is not greater than 2.0, in particular not greater than 1.5, and more preferably not greater than 1.0.
  • the pigment preparations according to the invention are preferably highly crystalline, characterized by a half-width HWB of the main peak of 0.2 to 0.7 ° 2Theta, in particular from 0.3 to 0.5 ° 2Theta, in the X-ray powder diffractogram with CuK a ⁇ P h a radiation.
  • the pigment preparations according to the invention contain the base pigment having an average particle size d 50 of 20 to 100 nm, preferably 30 to 80 nm.
  • the particle size distribution of Cl. Pigment Red 254 is preferably approximated to a Gaussian distribution in which the standard deviation is Sigma preferably less than 40 nm, more preferably less than 30 nm. As a rule, the standard deviations are between 5 and 40 nm, preferably between 10 and 30 nm.
  • the pigment preparations according to the invention surprisingly have a very low viscosity, preferably a viscosity of 3 to 50 mPa-s, measured at 20 0 C using a cone-plate viscometer, such as RS75 of Messrs. Haake.
  • the pigment preparations according to the invention can in addition to
  • Diketopyrrolopyrrolpigment and the Pigmentdispergator contain other conventional auxiliaries or additives, such as surfactants, dispersants, fillers, extenders, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants, UV absorbers and light stabilizers, preferably in in an amount of 0.1 to 10 wt .-%, in particular 0.5 to 5 wt .-%, based on the total weight of the pigment preparation.
  • auxiliaries or additives such as surfactants, dispersants, fillers, extenders, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants, UV absorbers and light stabilizers, preferably in in an amount of 0.1 to 10 wt .-%, in particular 0.5 to 5 wt .-%, based on the total weight of the
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic or amphoteric substances or mixtures of these agents.
  • Suitable 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,
  • Resins for example, rosin-modified Maleinatharze and condensation products based on cyanuric chloride, taurine, N, N'-diethylamino-propylamine and p-phenylenediamine into consideration.
  • Preferred are rosin soaps, i. Alkali salts of resin acids.
  • 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, in particular 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 g of the polyaminoamido or polyamino compound, and salts of these cationic substances, such as acetates or chlorides into consideration.
  • nonionic and amphoteric substances are 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,
  • 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 preparation of color filters 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.
  • Substances carry polar anchor groups such as hydroxy, amino, imino and ammonium groups, carboxylic acid and carboxylate groups, sulfonic acid and sulfonate groups or phosphonic acid and phosphonate groups, and may also be modified with aromatic, non-pigmentary substances.
  • 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, aminoalcohols or diamines 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, cyanuric halide-based condensation products, nitroxyl-containing polymers, polyesteramides, modified polyamides, modified acrylic polymers, comb-like structure dispersants of polyesters and acrylic polymers, phosphoric acid esters derived from triazine 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.
  • 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 pulverulent nature.
  • the invention also provides a process for the preparation of a pigment preparation according to the invention, characterized in that Cl. Pigment Red 254 before or during kneading, wet grinding, dry grinding or finish treatment with the pigment dispersant of the formula (II).
  • the dry components may be mixed in granule or powder form 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, acids or grinding aids such as salt.
  • the mixing can also be carried out by adding the pigment dispersant during the production process of C.I. Pigment Red 254.
  • the addition of the pigment dispersant to the C.I. Pigment Red 254 is preferably carried out after the chemical formation of C.I. Pigment Red 254 and before or during the formation of the fine particles.
  • the pigment dispersant is added to the diketopyrrolopyrrole pigment during dry or wet grinding.
  • the finely crystalline pigment preparation formed in this case can be subjected to a post-treatment, generally referred to as finish, for example in water and / or solvents and usually under elevated temperature, for example up to 200 ° C., and optionally elevated pressure.
  • finish for example in water and / or solvents and usually under elevated temperature, for example up to 200 ° C., and optionally elevated pressure.
  • the pigment dispersant may also be added after dry or wet milling, but before or during the finish.
  • the pigment dispersant can also be added in partial portions at different times.
  • 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.
  • the pigment preparations according to the invention are distinguished by their 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. Such pigment dispersions show excellent rheological properties even with high pigmentation of the coating or printing ink concentrates. Other properties, such as gloss, overcoating fastness, solvent fastness, alkali and acid fastness, light and weather fastness and high purity of hue, are very good.
  • hues in the red range which are required when used in color filters can be achieved.
  • hues in the red range which are required when used in color filters can be achieved.
  • they ensure high contrast and also satisfy the other requirements imposed on color filters, such as high temperature stability or steep and narrow absorption bands. They can be produced with high purity and low levels of ions.
  • the pigment preparations according to the invention can be used in principle for pigmenting all high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, paints, in particular metallic paints, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks.
  • plastics for example plastics, resins, paints, in particular metallic paints, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks.
  • High molecular weight organic materials which can be pigmented with the pigment preparations according to the invention are, for example, cellulose compounds, such as cellulose ethers and esters, such as ethylcellulose, nitrocellulose, cellulose acetates or cellulose butyrates, natural binders, such as, for example, fatty acids, fatty oils, resins and their conversion products, or synthetic resins , such as polycondensates, polyadducts, polymers and copolymers, such as, for example, aminoplasts, in particular urea and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenoplasts 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, poly
  • 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 of the invention is usually used in an amount of from 0.01 to 30% by weight, preferably from 0.1 to 20% by weight. For color filter applications, higher colorant concentrations can also be used.
  • the pigment preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as, for example, one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, polymerization toners and special toners.
  • 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 subsequently modified with these additives.
  • 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 subsequently modified with these additives.
  • the pigment preparations according to the invention are suitable as colorants in powders and powder coatings, in particular in triboelectrically or electrokinetically sprayable powder coatings, which are used for surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • the pigment preparations according to the invention are suitable as colorants in aqueous and nonaqueous based ink-jet inks and also in inks which work according to the hot-melt method.
  • Ink-jet inks generally contain a total of 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, (calculated dry) of the pigment preparation of 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 the 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 the 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 about 140 ° C.
  • hot melt ink jet inks consist essentially of 20 to 90% by weight of wax and 1 to 10% by weight of the invention
  • Polymer (as a "dye remover"), 0 to 5 wt .-% dispersing aid, 0 to
  • the pigment preparations according to the invention are colorants for color filters, both for additive and for subtractive color generation, such as in electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays, which in turn can be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, as well as colorants for electronic inks ("electronic inks" or "e-inks”) or “electronic paper” (“e-paper ”) suitable.
  • electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays, which in turn can be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, as well as colorants for electronic inks ("electronic inks" or "e-inks”) or “electronic paper” (“e-paper ”) suitable.
  • pigments in the form of a paste or as pigmented photoresists in suitable binders acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins
  • suitable binders acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatin, caseins
  • a stable paste or a pigmented photoresist also has a high pigment purity
  • the pigmented Color Filter can also by
  • Ink jet printing process or other suitable printing process can be applied.
  • the red shades of the pigment preparations according to the invention are particularly well suited for the Color Filter Red-Green-Blue color set (R 1 G 1 B). These three colors are present as separate color dots side by side, and result from backlit a full color image.
  • Typical colorants for the red color point are pyrrolopyrrole, quinacridone and
  • Azo pigments e.g. Cl. Pigment Red 254, Cl. Pigment Red 209, Cl. Pigment Red 175 and Cl. Pigment Orange 38, single or mixed.
  • Color point typically phthalocyanine colorants are used, such.
  • Example 1 Bead grinding of C.I. Pigment Red 254 in the presence of 10% of the pigment dispersant:
  • Example 2 Bead milling of C.I. Pigment Red 254 and addition of 10% of the pigment dispersant prior to solvent treatment
  • a mixture of 90 parts of PR 254, 1, 8 parts of a commercial flow improver based on naphthalenesulfonic acid and 800 parts of water is a homogeneous paste, and (with a Drais Advantis ® V3 mill in the presence of 800 parts of zirconia beads 0.4 to 0, 6 mm).
  • the grinding time corresponds to five to six theoretical grinding passages.
  • 7.40 parts of the 10% grinding suspension are mixed with 7.4 parts of a pigment dispersant (V) and isobutanol to form a 1: 1 mixture of isobutanol and water.
  • the suspension is heated at pH 2 for 2 h to reflux, filtered off after separation of the isobutanol by steam distillation, washed free of salt with water, dried in vacuo and finally pulverized.
  • Example 5 Bead grinding of C.I. Pigment Red 254 and addition of 10% of the pigment dispersant before a solvent treatment:
  • Example 7 Bead grinding of CI Pigment Red 254 in the presence of 10% of the pigment dispersant:
  • Example 8 Bead grinding of C.I. Pigment Red 254 and addition of 10% of the pigment dispersant before a solvent treatment:
  • Example 10 Pearl Milling of C.I. Pigment Red 254 in the Presence of 10% of the Pigment Dispersant
  • Example 11 Bead milling of C.I. Pigment Red 254 and addition of 10% of the pigment dispersant before a solvent treatment:
  • Example 2 The procedure is analogous to Example 2, except that a pigment dispersant of the formula (VIII) is used. A red pigment preparation having a mean particle size d 50 of 62 nm (TEM) is obtained.
  • Comparative Example A Bead grinding of C.I. Pigment Red 254 without one
  • a mixture of 90 parts of PR 254, 1, 8 parts of a commercially available naphthalenesulfonic acid-based flow improver and 800 parts of water is homogeneously pasted and with a Drais® Advantis V3 mill in the presence of 800 parts zirconium oxide beads (0.4-0.6 mm) ground.
  • the grinding time corresponds to five to six theoretical grinding passages.
  • the millbase is mixed with isobutanol to give a 1: 1 mixture of isobutanol and water.
  • the suspension is heated at pH 2 for 2 h to reflux, filtered off after separation of the isobutanol by steam distillation, washed free of salt with water, dried in vacuo and finally pulverized. This gives a red pigment preparation having an average particle size d 50 of 102 nm (TEM).
  • the primary particles are visually identified.
  • the area of each primary particle is determined by means of a graphic tablet. From the
  • Area is the diameter of the area of the same circle determined.
  • Frequency distribution of the calculated equivalent diameter is determined and the frequencies are converted into volume fractions and as
  • the default distribution is a measure of the width of the distribution. The smaller the
  • Standard deviation is, the narrower is the particle size distribution.
  • Half width HWB is the width of the half-height reflex
  • the half-width of the samples is measured using a STOE / ⁇ diffractometer
  • Standard steel beams used.
  • the measuring time is at the desired statistical
  • the measurement is from 23 - 30 ° with a step size of 0.02 ° and a time period of 6 s.
  • the X-ray beam is monochromatized by a graphite secondary monochromator and scanned with a continuous scintillation counter
  • the pigment preparations described are applied to glass plates (SCHOTT, laser-cut, 10 ⁇ 10 cm) with the aid of a spin coater (POLOS Wafer Spinner). Due to the low viscosities, brilliant, highly transparent, red colorations with a small layer thickness (500 to 1300 nm) and very good contrast value (TSUBOSAKAELECTRIC CO..LTD, model CT-1) are obtained, which differ only slightly from the color of the non-additized samples.
  • the pigment preparations of Examples 1 to 14 are well suited for color filter applications because of their high contrast value.
  • Pigment mixtures were the resulting pigments in a transparent
  • Alkyd-melamine-tinted lacquers were mixed with 20.0 g of a 30% white lacquer.
  • the resulting whitening lacquer was mounted together with the sample to be compared side by side on a white cardboard card and after 30 min

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Medicinal Preparation (AREA)
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Abstract

La présente invention concerne une préparation pigmentaire caractérisée en ce qu'elle contient un pigment Red 254 du Colour Index (CI) présentant une taille particulaire moyenne située entre 20 et 100 nm, ainsi qu'un agent dispersant de pigment de formule (II) dans laquelle Q1 représente un groupement d'un pigment organique choisi dans le groupe formé par un pigment Red 264 du Colour Index et un pigment Violet 19 du Colour Index.
PCT/EP2008/001308 2007-03-07 2008-02-20 Préparations pigmentaires à base de dicétopyrrolopyrroles WO2008107075A2 (fr)

Applications Claiming Priority (2)

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DE102007011066.0 2007-03-07
DE102007011066A DE102007011066A1 (de) 2007-03-07 2007-03-07 Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolen

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WO2008107075A2 true WO2008107075A2 (fr) 2008-09-12
WO2008107075A3 WO2008107075A3 (fr) 2009-07-16

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DE (1) DE102007011066A1 (fr)
TW (1) TW200902641A (fr)
WO (1) WO2008107075A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008032090A1 (de) * 2008-07-08 2010-01-14 Clariant International Ltd. PR 254-Pigmentzubereitung zur Verwendung in Colorfiltern

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001004215A2 (fr) * 1999-07-09 2001-01-18 Ciba Specialty Chemicals Holding Inc. Pigments aux proprietes colorantes ameliorees et processus de preparation de ceux-ci
EP1104789A2 (fr) * 1999-12-02 2001-06-06 Clariant GmbH Dispersants pour pigments à base de dicétopyrrolopyrroles et dispersions de pigments
WO2002064680A1 (fr) * 2001-02-10 2002-08-22 Clariant Gmbh Agents dispersants pigmentaires acides et preparations pigmentaires
WO2007045312A2 (fr) * 2005-10-21 2007-04-26 Clariant Produkte (Deutschland) Gmbh Procede de production d'un rouge pigmentaire 264 a fines particules du colour index
WO2007045311A1 (fr) * 2005-10-21 2007-04-26 Clariant Produkte (Deutschland) Gmbh Préparations pigmentaires à base de dicétopyrrolopyrroles

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001004215A2 (fr) * 1999-07-09 2001-01-18 Ciba Specialty Chemicals Holding Inc. Pigments aux proprietes colorantes ameliorees et processus de preparation de ceux-ci
EP1104789A2 (fr) * 1999-12-02 2001-06-06 Clariant GmbH Dispersants pour pigments à base de dicétopyrrolopyrroles et dispersions de pigments
WO2002064680A1 (fr) * 2001-02-10 2002-08-22 Clariant Gmbh Agents dispersants pigmentaires acides et preparations pigmentaires
WO2007045312A2 (fr) * 2005-10-21 2007-04-26 Clariant Produkte (Deutschland) Gmbh Procede de production d'un rouge pigmentaire 264 a fines particules du colour index
WO2007045311A1 (fr) * 2005-10-21 2007-04-26 Clariant Produkte (Deutschland) Gmbh Préparations pigmentaires à base de dicétopyrrolopyrroles

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DE102007011066A1 (de) 2008-09-11
TW200902641A (en) 2009-01-16
WO2008107075A3 (fr) 2009-07-16

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