EP1689817A1 - Pigment compositions consisting of a yellow disazo pigment and an organic pigment - Google Patents

Pigment compositions consisting of a yellow disazo pigment and an organic pigment

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Publication number
EP1689817A1
EP1689817A1 EP04797818A EP04797818A EP1689817A1 EP 1689817 A1 EP1689817 A1 EP 1689817A1 EP 04797818 A EP04797818 A EP 04797818A EP 04797818 A EP04797818 A EP 04797818A EP 1689817 A1 EP1689817 A1 EP 1689817A1
Authority
EP
European Patent Office
Prior art keywords
pigment
organic
red
composition according
orange
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04797818A
Other languages
German (de)
French (fr)
Inventor
Joachim Weber
Gerhard Wilker
Frank Alfter
Hans-Tobias Macholdt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1689817A1 publication Critical patent/EP1689817A1/en
Withdrawn legal-status Critical Current

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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
    • 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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/091—Azo dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices

Definitions

  • the invention relates to pigment compositions of a yellow disazo pigment and an organic orange, red or violet pigment and their use for coloring high molecular weight materials.
  • pigment suspensions are towards high pigment concentrations, which is why highly pigmented lacquer and printing ink concentrates or millbases (mill base) with a low viscosity are required.
  • Other areas of application of pigments are, for example, electrophotographic toners, inks, color filters or powder coatings, each of which has its own special requirements.
  • JP 2003-232914 discloses pigment compositions containing C.I. Pigment Yellow 214.
  • the invention relates to pigment compositions containing a disazo pigment of the formula (I),
  • pigments from the group of the organic orange, red and violet pigments.
  • the organic orange and red pigment in the composition according to the invention are C.I. Pigment Orange 5, 13, 14, 16, 34, 36, 38, 42, 43, 48, 49, 51, 61, 62, 64, 67, 68, 69, 71, 72, 73, 74; C.I.
  • Preferred organic red pigments are Cl Pigment Red 7, 12, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 122, 146, 168, 177 , 178, 179, 184, 185, 187, 200, 202, 206, 207, 208, 209, 210, 246, 254, 255, 257, 264, 272, particularly Cl Pigment Red 122, 168, 177, 178, 179, 202, 209, 254, 255, 257, 264, 272.
  • Preferred organic orange pigments are C.I. Pigment Orange 43, 64, 71 and 73.
  • Preferred organic violet pigment is the C.I. Pigment Violet 19 in the gamma crystal modification.
  • the disazo pigment of the formula (I) and the organic orange, red or violet pigment can form a common crystal lattice, for example in the form of solid solutions or mixed crystals.
  • hues from yellowish red to orange to reddish yellow can be achieved; they are of particular interest for hues in yellowish red and in the orange range.
  • the pigment compositions according to the invention can be prepared in various ways, for example by mixing the dry components in granular or powder form before or after grinding, by adding one component in the moist to the other component in the moist or dry form, for example by mixing the components in the form the moist press cake.
  • Mixing can be carried out, for example, by acid pasting, acid swelling, by grinding in dry form, in moist form, for example 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 process for the preparation of the disazo pigment of the formula (I) comprises diazotizing the underlying aromatic amine to give the diazonium salt, if appropriate dissolving and possibly precipitating the underlying coupling component, mixing the two reactants diazonium salt and coupling component, the coupling component being added to the diazonium salt or vice versa can or a continuous azo coupling, possibly in a microreactor, can be carried out.
  • the resulting dome suspension can be subjected to an aftertreatment, for example after adding solvent, under elevated temperature and / or pressure.
  • the manufacturing process also includes the isolation of the co-product and, if necessary, an aftertreatment of the co-product in an aqueous, aqueous-organic or organic medium under elevated temperature, if necessary under pressure, with subsequent isolation of the azo pigment as a press cake and its drying and optionally grinding a granulate to powder.
  • the manufacturing process corresponds to that described above.
  • the disazo pigment of the formula (I) is usually added after the chemical synthesis of the ring system of the organic orange, red or violet pigment has been completed, since this usually takes place under reaction conditions which can lead to decomposition of the disazo pigment of the formula (I).
  • the organic orange, red or violet pigment is optionally subjected to comminution, for example by acid pasting, acid swelling, dry or wet grinding.
  • the fine crystalline obtained or obtained in the synthesis fine crystalline Organic orange, red and violet pigments are usually subjected to an aftertreatment, generally referred to as a finish, for example in water and / or solvents and usually under elevated temperature and possibly increased pressure.
  • drying units such as drying cupboards, paddle wheel dryers, tumble dryers, contact dryers and in particular spin flash and spray dryers, can be used for drying.
  • a suitable drying unit low-dust and free-flowing powders or granules can also be produced.
  • the pigment compositions are preferably prepared by grinding the components in dry form, in moist form or in suspension, in particular by salt kneading the components.
  • the specific surface area should be above 40 m 2 / g, preferably from 40 to 180 m 2 / g, in particular 60 to 160 m 2 / g.
  • the preferred manufacturing process for this is salt kneading.
  • colorants for shading and auxiliaries can be used, such as, for example, surfactants, non-pigmentary and pigmentary dispersants, fillers, adjusting agents, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, preservatives, drying retardants, additives for controlling the rheology , Wetting agents, antioxidants, UV absorbers, light stabilizers, binders, for example the binders of the system in which the pigment composition according to the invention is to be used, or a combination thereof.
  • surfactants such as, for example, surfactants, non-pigmentary and pigmentary dispersants, fillers, adjusting agents, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, preservatives, drying retardants, additives for controlling the rheology , Wetting agents, antioxidants, UV absorbers, light stabilizers, binders, for example the binders of the system in which the pigment composition according to the invention
  • Shading components are usually used in amounts of up to 10% by weight and auxiliaries up to ten times the amount, in each case based on the total amount of disazo pigment of the formula (I) and organic orange, red or violet pigment. In exceptional cases, however, higher quantities can also occur.
  • the addition of tools and the shading colorant can occur at any point in the process.
  • Fillers or extenders mean a large number of substances in accordance with DIN 55943 and DIN EN 971-1, for example the different types of talc, kaolin, mica, dolomite, lime, titanium dioxide, zinc sulfide, lithopone or barium sulfate. The addition has proven particularly useful before grinding the pigment composition according to the invention.
  • the pigment compositions according to the invention can be used as preferably aqueous press cakes or moist granules, but as a rule they are solid systems of free-flowing, powdery nature or granules.
  • the pigment compositions according to the invention can be used to pigment high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks and seeds.
  • High molecular weight organic materials that can be pigmented with the pigment compositions according to the invention are, for example, cellulose compounds, such as, for example, cellulose ethers and esters, such as ethyl cellulose, 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 phenol resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl ether polyolefins, or polyvinyl ether polyolefins, or polyvinyl ether polyo
  • the high-molecular organic compounds mentioned are in the form of plastic masses, melts or in the form of spinning solutions, dispersions, lacquers, paints or printing inks.
  • the pigment compositions according to the invention it proves advantageous to use as a blend or in the form of preparations or dispersions. It is also possible to prepare the pigment composition only when it is incorporated into the high-molecular organic medium.
  • the invention therefore also relates to a high molecular weight organic medium containing a dye-effective amount of an agent according to the invention
  • the pigment compositions according to the invention are usually used in an amount of from 0.01 to
  • This crude can be used to produce color concentrates in liquid or solid form in concentrations of 5 to 99% by weight, alone or optionally in a mixture with other crudes or finished pigments.
  • the pigment compositions of 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.
  • 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, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • the pigment compositions 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 the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • Epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are typically used as powder coating resins together with conventional hardeners. Combinations of resins are also used. For example, epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and dicyandiamide and their derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • the pigment compositions according to the invention are suitable as colorants in ink-jet inks on an aqueous and non-aqueous basis and in inks which work according to the hot-melt process.
  • Ink-jet inks generally contain a total of 0.5 to 15% by weight, preferably 1.5 to 8% by weight (calculated on a dry basis) of one or more of the pigment compositions according to the invention.
  • Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator).
  • Microemulsion inks generally contain 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, of one or more of the invention Pigment compositions, 5 to 99% by weight of water and 0.5 to 94.5% by weight of organic solvent and / or hydrotropic compound.
  • “Solvent based" ink-jet inks preferably contain 0.5 to 15% by weight of one or more of the pigment compositions according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds.
  • Hot-melt inks are mostly based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx.
  • Hot-melt ink-jet inks essentially consist, for example, of 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the pigment compositions according to the invention. Furthermore, 0 to 20% by weight of an additional polymer (as a "dye dissolver"), 0 to 5% by weight of dispersing aid, 0 to 20% by weight of viscosity modifier, 0 to 20% by weight of plasticizer, 0 to 10% by weight % Stickiness additive, 0 to 10% by weight transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight antioxidant.
  • an additional polymer as a "dye dissolver”
  • dispersing aid 0 to 20% by weight of viscosity modifier
  • plasticizer 0 to 20% by weight of plasticizer
  • Stickiness additive 0 to 10% by weight
  • transparency stabilizer prevents, for example, crystallization of the waxes
  • the pigment compositions according to the invention are also used as colorants for color filters, both for additive and for subtractive color generation, for example in electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays can in turn 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 ").
  • a high pigment purity is also required for a stable paste or pigmented photoresist Requirement.
  • the pigmented color filters can also be applied by ink jet printing processes or other suitable printing processes.
  • the pigment compositions according to the invention are notable for their outstanding coloristic and rheological properties, in particular high flocculation stability, easy dispersibility, good rheology, high color strength and saturation (chroma). They are light in many application media and dispersible to high fineness. Such pigment dispersions show excellent rheological properties even with high pigmentation of the paint color concentrates.
  • the other properties mentioned above, such as gloss, fastness to overcoating, fastness to solvents, fastness to alkali, fastness to light and weather and high purity of the color are also very good.
  • the pigment compositions according to the invention can be used to achieve hues in the yellowish red and orange range which are in demand when used in color filters. Here they provide very good contrast.
  • pigment compositions can be manufactured with high purity and low levels of ions. Depending on requirements, pigment compositions with a high or low specific surface, with opaque or transparent full tones can be produced.
  • the pigment compositions according to the invention also show excellent properties when one component, in particular the yellow disazo pigment of the formula (I), is used for tinting only in relatively small amounts.
  • an alkyd-melamine resin paint based on a medium-oil alkyd resin and a butanol-etherified melamine resin (AM) was selected from the large number of known paints.
  • an aqueous lacquer based on polyurethane (PUR) was selected from the large number of known lacquer systems.
  • the coloristic properties were determined in accordance with DIN 55986.
  • the rheology of the mill base after dispersion was assessed visually using the following five-point scale.
  • the fastness to overcoating was determined in accordance with DIN 53221.
  • the viscosity was determined after the millbase had been diluted to the final pigment concentration using the Rossmann viscose spatula, type 301 from Erichsen.
  • the pigment composition in the AM varnish provides strong color varnishes with a reddish-orange hue.
  • the pigment composition in the AM varnish provides strong paint finishes with a reddish-orange and pure color.
  • the full tone is transparent. Examples 3 to 8
  • Formula (I) are mixed mechanically.
  • Example 11a 450 g of sodium chloride, 75 g of disazo pigment of the formula (I), prepared according to DE 10045790 A1 Example 2, and 110 ml of diethylene glycol are kneaded at 85 ° C. for 8 hours.
  • the modeling clay is stirred in 4 liters of 5% strength by weight aqueous sulfuric acid at 40 ° C. for 2 hours, the suspension is filtered, the presscake is washed free of salt and dried at 80 ° C. 74 g of disazo pigment of the formula (I) are obtained.
  • Example 11b 18 g C.I. Pigment Red 254 and 2 g of disazo pigment of the formula (I), prepared according to Example 11a, are mixed mechanically.
  • Example 12 15 g C.I. Pigment Red 254, 3 g C.I. Pigment Red 264 and 2 g of disazo pigment of the formula (I), prepared according to Example 11a, are mixed mechanically.
  • a color filter paste which consists of pigment composition, binder, solvent and dispersion aid according to the following recipe: 77% by weight 1-methoxy-2-propyl acetate 10% by weight styrene acrylic polymer 10% by weight pigment composition; and 3% by weight dispersing aid.
  • the above mixture is dispersed with zircon balls (0 0.5-0.7 mm) in a paint shaker for 2 hours. The dispersion is then filtered.
  • the color filter paste obtained is applied to a glass substrate using a spin coater to produce a color filter film. The transparency, coloristic values, heat stability and contrast are determined on this color filter film.
  • the transmission of the coated glass substrate is determined spectrophotometrically in the application range from 400 to 700 nm.
  • the coloristic values are described with the CIE color triangle (xyY values): x describes the blue-red axis, y the blue-green axis, Y the brilliance.
  • the viscosity is determined on the color filter paste described above using a rotary viscometer at a temperature of 23 ° C ⁇ 0.5 ° C and at a shear rate of 60s "1 .
  • the heat stability is described by the delta E value;
  • the delta E value is determined according to DIN 6174, it describes the total color difference and can be calculated from the x, y, y values.
  • the coated glass substrate is tempered for 10 minutes at 80 ° C.
  • the transmission is then measured and the delta E calculated.
  • the coated glass substrate is then tempered at 250 ° C. for 1 h and again a delta E value is determined.
  • the color filter paste is used to produce a full-tone coating and, after dilution with a white paste, a so-called brightening coating by knife coating, the color characteristics of which are assessed.
  • a color filter paste is produced.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paintwork shows high transparency and color strength and a pure color.
  • a color filter paste is produced.
  • the viscosity of the color filter paste is: ⁇ - 23.2 mPa.s. 3 ml of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a rotational speed of 2500 rpm for 20 s.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paintwork shows high transparency and color strength and a pure color.
  • a color filter paste is produced.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paintwork shows high transparency and color strength and a pure color.

Abstract

The invention relates to a pigment composition containing a disazo pigment of formula (I), and at least one pigment from the group of organic orange, red and violet pigments.

Description

Beschreibung description
Pigmentzusammensetzungen aus gelbem Disazopigment und organischem PigmentPigment compositions of yellow disazo pigment and organic pigment
Die Erfindung betrifft Pigmentzusammensetzungen aus einem gelben Disazopigment und einem organischen Orange-, Rot- oder Violetpigment und ihre Verwendung zum Färben von hochmolekularen Materialien.The invention relates to pigment compositions of a yellow disazo pigment and an organic orange, red or violet pigment and their use for coloring high molecular weight materials.
Beim Einsatz von Pigmenten zum Färben von hochmolekularen organischen Materialien werden hohe Anforderungen an die anwendungstechnischen Eigenschaften der Pigmente gestellt, wie leichte Dispergierbarkeit, anwendungsgerechte Fließfähigkeit der Lacke, hohe Farbstärke, Überlackierechtheit, Lösemittelechtheit, Beständigkeit gegen Alkali und Säure, Licht- und Wetterechtheiten und Reinheit des Farbtons. Außerdem ist eine möglichst universelle Ersetzbarkeit zum Färben von anderen hochmolekularen Systemen, wie beispielsweise von Kunststoffen und Druckfarben, wünschenswert. Hier kommen weitere teilweise auch an Lacke gestellte Anforderungen hinzu, wie beispielsweise hohe Echtheiten wie Ausblutechtheit und Hitzestabilitäten. Bei Lacken und Druckfarben wird die Ersetzbarkeit sowohl in wasser- als auch in lösemittelbasierenden Systemen gewünscht. Der Trend bei der Herstellung von Pigmentsuspensionen geht hin zu hohen Pigmentkonzentrationen, daher werden hochpigmentierte Lack- und Druckfarbenkonzentrate oder Mahlgüter (mill base) mit dennoch niedriger Viskosität gefordert. Weitere Einsatzgebiete von Pigmenten sind beispielsweise elektrophotographische Toner, Tinten, Farbfilter, oder Pulverlacke, die jeweils ihre zusätzlichen, speziellen Anforderungen haben.When using pigments for coloring high-molecular organic materials, high demands are placed on the application properties of the pigments, such as easy dispersibility, application-oriented flowability of the lacquers, high color strength, fastness to overcoating, fastness to solvents, resistance to alkali and acid, light and weather fastness and purity hue. In addition, it is desirable to be as universal as possible for dyeing other high-molecular systems, such as plastics and printing inks. There are further requirements, some of which are also placed on paints, such as high fastness properties such as fastness to bleeding and heat stability. With lacquers and printing inks, replaceability in both water and solvent-based systems is desired. The trend in the production of pigment suspensions is towards high pigment concentrations, which is why highly pigmented lacquer and printing ink concentrates or millbases (mill base) with a low viscosity are required. Other areas of application of pigments are, for example, electrophotographic toners, inks, color filters or powder coatings, each of which has its own special requirements.
Die JP 2003-232914 offenbart Pigmentzusammensetzungen enthaltend C.l. Pigment Yellow 214.JP 2003-232914 discloses pigment compositions containing C.I. Pigment Yellow 214.
Durch die Eigenfarbe der Pigmente lassen sich die meisten Farbtöne nur durch Mischen zweier oder mehrerer Pigmente erzielen. Bei gewissen Farbtönen, besonders bei orangen Farbtönen, und auch beim Einsatz einer Komponente in niedrigen Mengen zum Einstellen des Farbtons, genügen die bekannten Lösungen nicht allen Anforderungen.Due to the inherent color of the pigments, most shades can only be achieved by mixing two or more pigments. With certain shades, especially with orange shades, and also when using a component in low amounts for adjusting the color, the known solutions do not meet all requirements.
Es bestand ein Bedarf an Pigmentzusammensetzungen, die Nachteile bekannter Pigmentzusammensetzungen überwinden und die den oben genannten Anforderungen genügen.There has been a need for pigment compositions that overcome disadvantages of known pigment compositions and that meet the above requirements.
Gegenstand der Erfindung sind Pigmentzusammensetzungen, enthaltend ein Disazopigment der Formel (I),The invention relates to pigment compositions containing a disazo pigment of the formula (I),
und ein oder mehrere, z.B. ein, zwei oder drei, Pigmente aus der Gruppe der organischen Orange-, Rot- und Violetpigmente. and one or more, for example one, two or three, pigments from the group of the organic orange, red and violet pigments.
Als organisches Orange- und Rotpigment in der erfindungsgemäßen Zusammensetzung kommen C.l. Pigment Orange 5, 13, 14, 16, 34, 36, 38, 42, 43, 48, 49, 51, 61, 62, 64, 67, 68, 69, 71, 72, 73, 74; C.l. Pigment Red 1, 2, 3, 4, 5, 7, 9, 12, 14, 23, 38, 41 , 42, 48, 48:1 , 48:2, 48:3, 48:4, 48:5, 48:6, 49, 49:1, 51:1, 52:1, 52:2, 53, 53:1, 53:3, 57, 57:1, 57:2, 57:3, 58:2, 58:4, 63:1, 81 , 81:1, 81:2, 81:3, 81:4, 81:5, 81:6, 88, 112, 122, 123, 144, 146, 148, 149, 150, 166, 168, 169, 170, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 192, 194, 200, 200:1 , 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 242, 246, 247, 251, 253, 254, 255, 256, 257, 260, 262, 264, 270, 272; C.l. Pigment Violet 19 in Frage.The organic orange and red pigment in the composition according to the invention are C.I. Pigment Orange 5, 13, 14, 16, 34, 36, 38, 42, 43, 48, 49, 51, 61, 62, 64, 67, 68, 69, 71, 72, 73, 74; C.I. Pigment Red 1, 2, 3, 4, 5, 7, 9, 12, 14, 23, 38, 41, 42, 48, 48: 1, 48: 2, 48: 3, 48: 4, 48: 5, 48: 6, 49, 49: 1, 51: 1, 52: 1, 52: 2, 53, 53: 1, 53: 3, 57, 57: 1, 57: 2, 57: 3, 58: 2, 58: 4, 63: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 81: 5, 81: 6, 88, 112, 122, 123, 144, 146, 148, 149, 150, 166, 168, 169, 170, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 192, 194, 200, 200: 1, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 242, 246, 247, 251, 253, 254, 255, 256, 257, 260, 262, 264, 270, 272; C.I. Pigment Violet 19 in question.
Bevorzugte organische Rotpigmente sind C.l. Pigment Red 7, 12, 14, 41, 48:1, 48:2, 48:3, 48:4, 81:1, 81:2, 81:3, 122, 146, 168, 177, 178, 179, 184, 185, 187, 200, 202, 206, 207, 208, 209, 210, 246, 254, 255, 257, 264, 272, insbesondere C.l. Pigment Red 122, 168, 177, 178, 179, 202, 209, 254, 255, 257, 264, 272.Preferred organic red pigments are Cl Pigment Red 7, 12, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 122, 146, 168, 177 , 178, 179, 184, 185, 187, 200, 202, 206, 207, 208, 209, 210, 246, 254, 255, 257, 264, 272, particularly Cl Pigment Red 122, 168, 177, 178, 179, 202, 209, 254, 255, 257, 264, 272.
Bevorzugte organische Orangepigmente sind C.l. Pigment Orange 43, 64, 71 und 73. Bevorzugtes organisches Violetpigment ist das C.l. Pigment Violet 19 in der gamma-Kristallmodifikation.Preferred organic orange pigments are C.I. Pigment Orange 43, 64, 71 and 73. Preferred organic violet pigment is the C.I. Pigment Violet 19 in the gamma crystal modification.
In den erfindungsgemäßen Pigmentzusammensetzungen kann das Disazopigment der Formel (I) und das organische Orange-, Rot oder Violetpigment ein gemeinsames Kristallgitter ausbilden, beispielsweise in Form von festen Lösungen oder Mischkristallen.In the pigment compositions according to the invention, the disazo pigment of the formula (I) and the organic orange, red or violet pigment can form a common crystal lattice, for example in the form of solid solutions or mixed crystals.
Mit den erfindungsgemäßen Pigmentzusammensetzungen lassen sich Farbtöne von gelbstichigen Rot über Orange zu rotstichigem Gelb erzielen, sie sind besonderes für Farbtöne im gelbstichigen Rot und im Orange-Bereich von Interesse.With the pigment compositions according to the invention, hues from yellowish red to orange to reddish yellow can be achieved; they are of particular interest for hues in yellowish red and in the orange range.
In den erfindungsgemäßen Pigmentzusammensetzungen kann das Gewichtsverhältnis Disazopigment der Formel (I) zu organischem Orange-, Rotoder Violetpigment (0,1 zu 99,9) bis (99,9 zu 0,1), bevorzugt (1 zu 99) bis (99 zu 1), besonders bevorzugt (5 zu 95) bis (95 zu 5) und insbesondere (10 zu 90) bis (90 zu 10), betragen.In the pigment compositions according to the invention, the weight ratio of disazo pigment of the formula (I) to organic orange, red or violet pigment (0.1 to 99.9) to (99.9 to 0.1), preferably (1 to 99) to (99 to 1), particularly preferably (5 to 95) to (95 to 5) and in particular (10 to 90) to (90 to 10).
Die erfindungsgemäßen Pigmentzusammensetzungen können auf verschiedene Weise hergestellt werden, beispielsweise durch Mischen der trockenen Komponenten in Granulat- oder Pulverform vor oder nach einer Mahlung, durch Zugabe der einen Komponente in feuchter zur anderen Komponente in feuchter oder trockener Form, beispielsweise durch Mischen der Komponenten in Form der feuchten Presskuchen.The pigment compositions according to the invention can be prepared in various ways, for example by mixing the dry components in granular or powder form before or after grinding, by adding one component in the moist to the other component in the moist or dry form, for example by mixing the components in the form the moist press cake.
Das Mischen kann beispielsweise durch Acidpasting, Acidswelling, durch eine Mahlung in trockener Form, in feuchter Form, beispielsweise eine Knetung, oder in Suspension erfolgen, oder durch eine Kombination dieser Verfahren. Die Mahlung kann unter Zusatz von Wasser, Lösemitteln, Säuren oder Mahlhilfsmitteln wie Salz durchgeführt werden.Mixing can be carried out, for example, by acid pasting, acid swelling, by grinding in dry form, in moist form, for example 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.
Das Mischen kann auch durch Zugabe der einen Komponente zur anderen Komponente während des Herstellungsprozess der letzteren Komponente erfolgen. Der Herstellprozess des Disazopigments der Formel (I) umfasst das Diazotieren des zugrundeliegenden aromatischen Amins zum Diazoniumsalz, ggf. das Lösen und ggf. das Fällen der zugrundeliegenden Kupplungskomponente, das Mischen der beiden Reaktionspartner Diazoniumsalz und Kupplungskomponente, wobei die Kupplungskomponente zum Diazoniumsalz oder umgekehrt zugegeben werden kann oder auch eine kontinuierliche Azokupplung, ggf. in einem Mikroreaktor, durchgeführt werden kann. Die entstandene Kuppelsuspension kann einer Nachbehandlung, beispielsweise nach Zugabe von Lösemittel, unter erhöhter Temperatur und/oder Druck unterworfen werden. Der Herstellprozess umfasst des weiteren die Isolierung des Kuppelprodukts und ggf. eine Nachbehandlung des Kuppelprodukts in einem wässrigen, wässrig-organischen oder organischen Medium unter erhöhter Temperatur, ggf. unter Druck, mit anschließender Isolierung des Azopigments als Presskuchen und seine Trocknung und ggf. eine Mahlung eines Granulats zu Pulver.Mixing can also be done by adding one component to the other component during the manufacturing process of the latter component. The process for the preparation of the disazo pigment of the formula (I) comprises diazotizing the underlying aromatic amine to give the diazonium salt, if appropriate dissolving and possibly precipitating the underlying coupling component, mixing the two reactants diazonium salt and coupling component, the coupling component being added to the diazonium salt or vice versa can or a continuous azo coupling, possibly in a microreactor, can be carried out. The resulting dome suspension can be subjected to an aftertreatment, for example after adding solvent, under elevated temperature and / or pressure. The manufacturing process also includes the isolation of the co-product and, if necessary, an aftertreatment of the co-product in an aqueous, aqueous-organic or organic medium under elevated temperature, if necessary under pressure, with subsequent isolation of the azo pigment as a press cake and its drying and optionally grinding a granulate to powder.
Wenn das organische Orange- oder Rotpigment ein Azopigment ist, entspricht der Herstellprozess dem oben beschriebenen.If the organic orange or red pigment is an azo pigment, the manufacturing process corresponds to that described above.
Ist das organische Orange-, Rot oder Violetpigment ein polycyclisches Pigment, geschieht die Zugabe des Disazopigments der Formel (I) gewöhnlicher Weise, nachdem die chemische Synthese des Ringsystems des organischen Orange-, Rot- oder Violetpigments abgeschlossen ist, da diese meist unter Reaktionsbedingungen geschieht, die zu einer Zersetzung des Disazopigments der Formel (I) führen können. Nach der chemischen Synthese wird das organische Orange-, Rot- oder Violetpigment gegebenenfalls einer Zerkleinerung unterzogen, beispielsweise durch Acidpasting, Acidswelling, Trocken- oder Nassmahlung. Die erhaltenen feinkristallinen oder bei der Synthese feinkristallin anfallenden organischen Orange-, Rot- und Violetpigmente werden meist einer Nachbehandlung, im allgemeinen als Finish bezeichnet, unterworfen, beispielsweise in Wasser und/oder Lösemitteln und meist unter erhöhter Temperatur und ggf. erhöhtem Druck.If the organic orange, red or violet pigment is a polycyclic pigment, the disazo pigment of the formula (I) is usually added after the chemical synthesis of the ring system of the organic orange, red or violet pigment has been completed, since this usually takes place under reaction conditions which can lead to decomposition of the disazo pigment of the formula (I). After chemical synthesis, the organic orange, red or violet pigment is optionally subjected to comminution, for example by acid pasting, acid swelling, dry or wet grinding. The fine crystalline obtained or obtained in the synthesis fine crystalline Organic orange, red and violet pigments are usually subjected to an aftertreatment, generally referred to as a finish, for example in water and / or solvents and usually under elevated temperature and possibly increased pressure.
Bei der Trocknung können die bekannten Trockenaggregate zum Einsatz kommen, wie Trockenschränke, Schaufelradtrockner, Taumeltrockner, Kontakttrockner und insbesondere Spinflash- und Sprühtrockner. Durch die Wahl eines geeigneten Trockenaggregates können auch staubarme und rieselfähige Pulver oder Granulate erzeugt werden.The known drying units, such as drying cupboards, paddle wheel dryers, tumble dryers, contact dryers and in particular spin flash and spray dryers, can be used for drying. By choosing a suitable drying unit, low-dust and free-flowing powders or granules can also be produced.
Bevorzugt werden die Pigmentzusammensetzungen durch Mahlung der Komponenten in trockener Form, in feuchter Form oder in Suspension hergestellt, insbesondere durch Salzknetung der Komponenten.The pigment compositions are preferably prepared by grinding the components in dry form, in moist form or in suspension, in particular by salt kneading the components.
Werden Pigmentzusammensetzungen in transparenter Form gewünscht, sollte die spezifische Oberfläche über 40 m2/g liegen, bevorzugt von 40 bis 180 m2/g, insbesondere 60 bis 160 m2/g. Der bevorzugte Herstellungsprozess hierfür ist die Salzknetung.If pigment compositions in transparent form are desired, the specific surface area should be above 40 m 2 / g, preferably from 40 to 180 m 2 / g, in particular 60 to 160 m 2 / g. The preferred manufacturing process for this is salt kneading.
Bei der Herstellung der erfindungsgemäßen Pigmentzusammensetzungen können weitere Farbmittel zum Nuancieren und Hilfsmittel eingesetzt werden, wie beispielsweise Tenside, nichtpigmentäre und pigmentäre Dispergiermittel, Füllstoffe, Stellmittel, Harze, Wachse, Entschäumer, Antistaubmittel, Extender, Antistatika, Konservierungsmittel, Trocknungsverzögerungsmittel, Additive zur Steuerung der Rheologie, Netzmittel, Antioxidantien, UV-Absorber, Lichtstabilisatoren, Bindemittel, beispielsweise die Bindemittel des Systems, in dem die erfindungsgemäße Pigmentzusammensetzung eingesetzt werden soll, oder eine Kombination davon. Nuancierkomponenten werden üblicher Weise in Mengen bis zu 10 Gew.-% und Hilfsmittel bis zur zehnfachen Menge, jeweils bezogen auf die Gesamtmenge Disazopigment der Formel (I) und organisches Orange-, Rot- oder Violetpigment, eingesetzt. Es können jedoch in Ausnahmefällen auch höhere Mengen vorkommen. Die Zugabe der Hilfsmittel und der Nuancierfarbmittel kann zu einem beliebigen Zeitpunkt im Verfahren geschehen.In the preparation of the pigment compositions according to the invention, further colorants for shading and auxiliaries can be used, such as, for example, surfactants, non-pigmentary and pigmentary dispersants, fillers, adjusting agents, resins, waxes, defoamers, anti-dusting agents, extenders, antistatic agents, preservatives, drying retardants, additives for controlling the rheology , Wetting agents, antioxidants, UV absorbers, light stabilizers, binders, for example the binders of the system in which the pigment composition according to the invention is to be used, or a combination thereof. Shading components are usually used in amounts of up to 10% by weight and auxiliaries up to ten times the amount, in each case based on the total amount of disazo pigment of the formula (I) and organic orange, red or violet pigment. In exceptional cases, however, higher quantities can also occur. The addition of tools and the shading colorant can occur at any point in the process.
Mit Füllstoffen bzw. Extendern sind eine Vielzahl von Substanzen gemäß DIN 55943 und DIN EN 971-1 gemeint, beispielsweise die verschiedenen Typen von Talk, Kaolin, Glimmer, Dolomit, Kalk, Titandioxid, Zinksulfid, Lithopone oder Bariumsulfat. Dabei hat sich die Zugabe besonders vor einer Mahlung der erfindungsgemäßen Pigmentzusammensetzung bewährt.Fillers or extenders mean a large number of substances in accordance with DIN 55943 and DIN EN 971-1, for example the different types of talc, kaolin, mica, dolomite, lime, titanium dioxide, zinc sulfide, lithopone or barium sulfate. The addition has proven particularly useful before grinding the pigment composition according to the invention.
Die erfindungsgemäßen Pigmentzusammensetzungen können als vorzugsweise wässriger Presskuchen oder Feuchtgranulat zum Einsatz kommen, in der Regel handelt es sich jedoch um feste Systeme von rieselfähiger, pulverförmiger Beschaffenheit oder um Granulate.The pigment compositions according to the invention can be used as preferably aqueous press cakes or moist granules, but as a rule they are solid systems of free-flowing, powdery nature or granules.
Die erfindungsgemäßen Pigmentzusammensetzungen lassen sich zum Pigmentieren von hochmolekularen organischen Materialien natürlicher oder synthetischer Herkunft einsetzen, beispielsweise von Kunststoffen, Harzen, Lacken, Anstrichfarben, elektrophotographischen Tonern und Entwicklern, Elektretmaterialien, Farbfiltern sowie von Tinten, Druckfarben und Saatgut.The pigment compositions according to the invention can be used to pigment high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks and seeds.
Hochmolekulare organische Materialien, die mit den erfindungsgemäßen Pigmentzusammensetzungen pigmentiert werden können, sind beispielsweise Celluloseverbindungen, wie beispielsweise Celluloseether und -ester, wie Ethylcellulose, Nitrocellulose, Celluloseacetate oder Cellulosebutyrate, natürliche Bindemittel, wie beispielsweise Fettsäuren, fette Öle, Harze und deren Umwandlungsprodukte, oder Kunstharze, wie Polykondensate, Polyaddukte, Polymerisate und Copolymerisate, wie beispielsweise Aminoplaste, insbesondere Harnstoff- und Melaminformaldehydharze, Alkydharze, Acrylharze, Phenoplaste und Phenolharze, wie Novolake oder Resole, Harnstoffharze, Polyvinyle, wie Polyvinylalkohole, Polyvinylacetale, Polyvinylacetate oder Polyvinylether, Polycarbonate, Polyolefine, wie Polystyrol, Polyvinylchlorid, Polyethylen oder Polypropylen, Poly(meth)acrylate und deren Copolymerisate, wie Polyacrylsäureester oder Polyacrylnitrile, Polyamide, Polyester, Polyurethane, Cumaron-Inden- und Kohlenwasserstoffharze, Epoxidharze, ungesättigte Kunstharze (Polyester, Acrylate) mit den unterschiedlichen Härtemechanismen, Wachse, Aldehyd- und Ketonharze, Gummi, Kautschuk und seine Derivate und Latices, Casein, Silikone und Silikonharze; einzeln oder in Mischungen. Dabei spielt es keine Rolle, ob die erwähnten hochmolekularen organischen Verbindungen als plastische Massen, Schmelzen oder in Form von Spinnlösungen, Dispersionen, Lacken, Anstrichstoffen oder Druckfarben vorliegen. Je nach Verwendungszweck erweist es sich als vorteilhaft, die erfindungsgemäßen Pigmentzusammensetzungen als Blend oder in Form von Präparationen oder Dispersionen zu benutzen. Es ist auch möglich, die Pigmentzusammensetzung erst bei der Einarbeitung in das hochmolekulare organische Medium herzustellen. Ebenfalls Gegenstand der Erfindung ist daher ein hochmolekulares organisches Medium, enthaltend eine färberisch wirksame Menge einer erfindungsgemäßenHigh molecular weight organic materials that can be pigmented with the pigment compositions according to the invention are, for example, cellulose compounds, such as, for example, cellulose ethers and esters, such as ethyl cellulose, 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 phenol resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl ether polyolefins, or polyvinyl ether polyolefins, or polyvinyl ether polyols, 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 (polyester, acrylates) with the different hardening mechanisms, waxes, aldehyde and ketone resins, rubber, rubber and its derivatives and latices, casein, silicones and silicone resins; individually or in mixtures. It does not matter whether the high-molecular organic compounds mentioned are in the form of plastic masses, melts or in the form of spinning solutions, dispersions, lacquers, paints or printing inks. Depending on the intended use, it proves advantageous to use the pigment compositions according to the invention as a blend or in the form of preparations or dispersions. It is also possible to prepare the pigment composition only when it is incorporated into the high-molecular organic medium. The invention therefore also relates to a high molecular weight organic medium containing a dye-effective amount of an agent according to the invention
Pigmentzusammensetzung.Pigment composition.
Bezogen auf das zu pigmentierende, hochmolekulare organische Material setzt man die erfindungsgemäßen Pigmentzusammensetzungen meist in einer Menge von 0,01 bisBased on the high-molecular organic material to be pigmented, the pigment compositions according to the invention are usually used in an amount of from 0.01 to
30 Gew.-%, vorzugsweise 0,1 bis 15 Gew.-%, ein.30% by weight, preferably 0.1 to 15% by weight.
Es ist in manchen Fällen auch möglich, anstelle einer gemahlenen und/oder gefinishten erfindungsgemäßen Pigmentzusammensetzung ein entsprechendesIn some cases it is also possible to use a corresponding pigment composition instead of a ground and / or finished pigment composition according to the invention
Crude mit einer BET-Oberfläche von größer als 2 m2/g, bevorzugt größer als 5 m2/g, einzusetzen. Dieser Crude kann zur Herstellung von Farbkonzentraten in flüssiger oder fester Form in Konzentrationen von 5 bis 99 Gew.-%, allein oder gegebenenfalls in Mischung mit anderen Crudes oder Fertigpigmenten, verwendet werden.Use crude with a BET surface area greater than 2 m 2 / g, preferably greater than 5 m 2 / g. This crude can be used to produce color concentrates in liquid or solid form in concentrations of 5 to 99% by weight, alone or optionally in a mixture with other crudes or finished pigments.
Die erfindungsgemäßen Pigmentzusammensetzungen sind auch geeignet als Farbmittel in elektrophotographischen Tonern und Entwicklern, wie beispielsweise Ein- oder Zweikomponentenpulvertonern (auch Ein- oder Zweikomponenten- Entwickler genannt), Magnettoner, Flüssigtoner, Polymerisationstoner sowie Spezialtoner. Typische Tonerbindemittel sind Polymerisations-, Polyadditions- und Polykondensationsharze, wie Styrol-, Styrolacrylat-, Styrolbutadien-, Acrylat-, Polyester-, Phenol-Epoxidharze, Polysulfone, Polyurethane, einzeln oder in Kombination, sowie Polyethylen und Polypropylen, die noch weitere Inhaltsstoffe, wie Ladungssteuermittel, Wachse oder Fließhilfsmittel, enthalten können oder im nachhinein mit diesen Zusätzen modifiziert werden.The pigment compositions of 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, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
Des weiteren sind die erfindungsgemäßen Pigmentzusammensetzungen geeignet als Farbmittel in Pulvern und Pulverlacken, insbesondere in triboelektrisch oder elektrokinetisch versprühbaren Pulverlacken, die zur Oberflächenbeschichtung von Gegenständen aus beispielsweise Metall, Holz, Kunststoff, Glas, Keramik, Beton, Textilmaterial, Papier oder Kautschuk zur Anwendung kommen. Als Pulverlackharze werden typischerweise Epoxidharze, carboxyl- und hydroxylgruppenhaltige Polyesterharze, Polyurethan- und Acrylharze zusammen mit üblichen Härtern eingesetzt. Auch Kombinationen von Harzen finden Verwendung. So werden beispielsweise häufig Epoxidharze in Kombination mit carboxyl- und hydroxylgruppenhaltigen Polyesterharzen eingesetzt. Typische Härterkomponenten (in Abhängigkeit vom Harzsystem) sind beispielsweise Säureanhydride, Imidazole sowie Dicyandiamid und deren Abkömmlinge, verkappte Isocyanate, Bisacylurethane, Phenol- und Melaminharze, Triglycidylisocyanurate, Oxazoline und Dicarbonsäuren.Furthermore, the pigment compositions 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 the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber. Epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are typically used as powder coating resins together with conventional hardeners. Combinations of resins are also used. For example, epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins. Typical hardener components (depending on the resin system) are, for example, acid anhydrides, imidazoles and dicyandiamide and their derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
Außerdem sind die erfindungsgemäßen Pigmentzusammensetzungen als Farbmittel in Ink-Jet Tinten auf wässriger und nichtwässriger Basis sowie in solchen Tinten, die nach dem Hot-melt-Verfahren arbeiten, geeignet. Ink-Jet-Tinten enthalten im allgemeinen insgesamt 0,5 bis 15 Gew.-%, vorzugsweise 1 ,5 bis 8 Gew.-%, (trocken gerechnet) einer oder mehrerer der erfindungsgemäßen Pigmentzusammensetzungen. Mikroemulsionstinten basieren auf organischen Lösemitteln, Wasser und ggf. einer zusätzlichen hydrotropen Substanz (Grenzflächenvermittler). Mikroemulsionstinten enthalten im allgemeinen 0,5 bis 15 Gew.-%, vorzugsweise 1 ,5 bis 8 Gew.-%, einer oder mehrerer der erfindungsgemäßen Pigmentzusammensetzungen, 5 bis 99 Gew.-% Wasser und 0,5 bis 94,5 Gew.-% organisches Lösungsmittel und/oder hydrotrope Verbindung. "Solvent based" Ink-Jet-Tinten enthalten vorzugsweise 0,5 bis 15 Gew.-% einer oder mehrerer der erfindungsgemäßen Pigmentzusammensetzungen, 85 bis 99,5 Gew.-% organisches Lösungsmittel und/oder hydrotrope Verbindungen. Hot-Melt-Tinten basieren meist auf wachsen, Fettsäuren, Fettalkoholen oder Sulfonamiden, die bei Raumtemperatur fest sind und bei Erwärmen flüssig werden, wobei der bevorzugte Schmelzbereich zwischen ca. 60°C und ca. 140°C liegt. Hot-Melt Ink-Jet-Tinten bestehen z.B. im wesentlichen aus 20 bis 90 Gew.-% Wachs und 1 bis 10 Gew.-% einer oder mehrerer der erfindungsgemäßen Pigmentzusammensetzungen. Weiterhin können 0 bis 20 Gew.-% eines zusätzlichen Polymers (als "Farbstofflöser"), 0 bis 5 Gew.-% Dispergierhilfsmittel, 0 bis 20 Gew.-% Viskositätsveränderer, 0 bis 20 Gew.-% Plastifizierer, 0 bis 10 Gew.-% Klebrigkeitszusatz, 0 bis 10 Gew.-% Transparenzstabilisator (verhindert z.B. Kristallisation der Wachse) sowie 0 bis 2 Gew.-% Antioxidans enthalten sein.In addition, the pigment compositions according to the invention are suitable as colorants in ink-jet inks on an aqueous and non-aqueous basis and in inks which work according to the hot-melt process. Ink-jet inks generally contain a total of 0.5 to 15% by weight, preferably 1.5 to 8% by weight (calculated on a dry basis) of one or more of the pigment compositions according to the invention. Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator). Microemulsion inks generally contain 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, of one or more of the invention Pigment compositions, 5 to 99% by weight of water and 0.5 to 94.5% by weight of organic solvent and / or hydrotropic compound. "Solvent based" ink-jet inks preferably contain 0.5 to 15% by weight of one or more of the pigment compositions according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds. Hot-melt inks are mostly based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx. 60 ° C and approx. 140 ° C. Hot-melt ink-jet inks essentially consist, for example, of 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the pigment compositions according to the invention. Furthermore, 0 to 20% by weight of an additional polymer (as a "dye dissolver"), 0 to 5% by weight of dispersing aid, 0 to 20% by weight of viscosity modifier, 0 to 20% by weight of plasticizer, 0 to 10% by weight % Stickiness additive, 0 to 10% by weight transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight antioxidant.
Weiterhin sind die erfindungsgemäßen Pigmentzusammensetzungen auch als Farbmittel für Farbfilter, sowohl für die additive wie auch für die subtraktive Farberzeugung, wie beispielsweise in elektro-optischen Systemen wie Fernsehbildschirmen, LCD (liquid crystal displays), Charge coupled devices, plasma displays oder electroluminescent displays, die wiederum aktive (twisted nematic) oder passive (supertwisted nematic) ferroelectric displays oder light- emitting diodes sein können, sowie als Farbmittel für elektronische Tinten („electronic inks" bzw. „e-inks") oder „electronic paper" („e-paper") geeignet. Bei der Herstellung von Farbfiltern, sowohl reflektierender wie durchsichtiger Farbfilter, werden Pigmente in Form einer Paste oder als pigmentierte Photoresists in geeigneten Bindemitteln (Acrylate, Acrylester, Polyimide, Polyvinylalkohole, Epoxide, Polyester, Melamine, Gelantine, Caseine) auf die jeweiligen LCD-Bauteilen (z.B. TFT-LCD = Thin Film Transistor Liquid Crystal Displays oder z.B. ((S) TN-LCD = (Super) Twisted Nematic-LCD) aufgebracht. Neben einer hohen Thermostabilität ist für eine stabile Paste bzw. einem pigmentierten Photoresist auch eine hohe Pigmentreinheit Voraussetzung. Darüber hinaus können die pigmentierten Color Filter auch durch Ink Jet- Druckverfahren oder andere geeignete Druckverfahren aufgebracht werden.Furthermore, the pigment compositions according to the invention are also used as colorants for color filters, both for additive and for subtractive color generation, for example in electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays can in turn 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 "). In the manufacture of color filters, both reflective and transparent color filters, pigments in the form of a paste or as pigmented photoresists in suitable binders (acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatins, caseins) are applied to the respective LCD components (eg TFT-LCD = Thin Film Transistor Liquid Crystal Displays or eg ((S) TN-LCD = (Super) Twisted Nematic-LCD). In addition to high thermal stability, a high pigment purity is also required for a stable paste or pigmented photoresist Requirement. In addition, the pigmented color filters can also be applied by ink jet printing processes or other suitable printing processes.
Die erfindungsgemäßen Pigmentzusammensetzungen zeichnen sich aus durch ihre hervorragenden coloristischen und rheologischen Eigenschaften, insbesondere hohe Flockungsstabilität, leichte Dispergierbarkeit, gute Rheologie, hohe Farbstärke und Sättigung (Chroma). Sie sind in vielen Anwendungsmedien leicht und bis zu hohen Feinheiten dispergierbar. Solche Pigmentdispersionen zeigen hervorragende rheologische Eigenschaften selbst bei hoher Pigmentierung der Lackfarbenkonzentrate. Auch die anderen oben erwähnten Eigenschaften wie beispielsweise Glanz, Uberlackierechtheit, Lösemittelechtheit, Alkaliechtheit, Licht- und Wetterechtheiten und hohe Reinheit des Farbtons sind sehr gut. Außerdem lassen sich mit den erfindungsgemäßen Pigmentzusammensetzungen Farbtöne im gelbstichigen Rot- und im Orange-Bereich erzielen, die beim Einsatz in Farbfiltern gefragt sind. Hier sorgen sie für sehr guten Kontrast. Sie können mit hoher Reinheit und niedrigen Gehalten an Ionen hergestellt werden. Je nach Anforderung können Pigmentzusammensetzungen mit hoher oder niedriger spezifischer Oberfläche, mit deckenden oder transparenten Volltönen hergestellt werden. Die erfindungsgemäßen Pigmentzusammensetzungen zeigen auch dann noch hervorragende Eigenschaften, wenn die eine Komponente, insbesondere das gelbe Disazopigment der Formel (I), nur in relativ niedrigen Mengen zum Abtönen eingesetzt wird.The pigment compositions according to the invention are notable for their outstanding coloristic and rheological properties, in particular high flocculation stability, easy dispersibility, good rheology, high color strength and saturation (chroma). They are light in many application media and dispersible to high fineness. Such pigment dispersions show excellent rheological properties even with high pigmentation of the paint color concentrates. The other properties mentioned above, such as gloss, fastness to overcoating, fastness to solvents, fastness to alkali, fastness to light and weather and high purity of the color are also very good. In addition, the pigment compositions according to the invention can be used to achieve hues in the yellowish red and orange range which are in demand when used in color filters. Here they provide very good contrast. They can be manufactured with high purity and low levels of ions. Depending on requirements, pigment compositions with a high or low specific surface, with opaque or transparent full tones can be produced. The pigment compositions according to the invention also show excellent properties when one component, in particular the yellow disazo pigment of the formula (I), is used for tinting only in relatively small amounts.
Zur Beurteilung der Eigenschaften der Pigmente auf dem Lacksektor in wasserfreien, lösemittelbasierenden Lacksystemen wurden aus der Vielzahl der bekannten Lacke ein Alkyd-Melaminharz-Lack auf Basis eines mittelöligen Alkydharzes und eines butanolveretherten Melaminharzes (AM) ausgewählt.To assess the properties of the pigments in the paint sector in water-free, solvent-based paint systems, an alkyd-melamine resin paint based on a medium-oil alkyd resin and a butanol-etherified melamine resin (AM) was selected from the large number of known paints.
Zur Beurteilung der Eigenschaften der Pigmente auf dem Lacksektor in wässrigen Lacksystemen wurde aus der Vielzahl der bekannten Lacksysteme ein wässriger Lack auf Polyurethanbasis (PUR) ausgewählt.To assess the properties of the pigments in the lacquer sector in aqueous lacquer systems, an aqueous lacquer based on polyurethane (PUR) was selected from the large number of known lacquer systems.
Die Bestimmung der coloristischen Eigenschaften erfolgte nach DIN 55986. Die Rheologie des Mahlguts nach der Dispergierung (millbase-Rheologie) wurde visuell anhand der folgenden fünfstufigen Skala bewertet.The coloristic properties were determined in accordance with DIN 55986. The rheology of the mill base after dispersion (millbase rheology) was assessed visually using the following five-point scale.
5 dünnflüssig 4 flüssig 3 dickflüssig 2 leicht gestockt 1 gestockt5 thin 4 liquid 3 viscous 2 lightly stocked 1 stocked
Die Bestimmung der Uberlackierechtheit erfolgte nach DIN 53221. Die Bestimmung der Viskosität erfolgte nach dem Verdünnen des Mahlguts auf die Pigmentendkonzentration mit dem Viskospatel nach Rossmann, Typ 301 der Firma Erichsen.The fastness to overcoating was determined in accordance with DIN 53221. The viscosity was determined after the millbase had been diluted to the final pigment concentration using the Rossmann viscose spatula, type 301 from Erichsen.
In den folgenden Beispielen bedeuten Prozentangaben Gewichtsprozente und Teile Gewichtsteile, sofern nicht anders angegeben. Das Disazopigment der Formel (I) wurde gemäß DE 10045790 A1 , Beispiel 2, hergestellt.In the following examples, percentages are percentages by weight and parts by weight, unless stated otherwise. The disazo pigment of the formula (I) was prepared in accordance with DE 10045790 A1, Example 2.
Beispiel 1example 1
18 g C.l. Pigment Red 177 und 12 g Disazopigment der Formel (I) werden mechanisch gemischt.18 g C.I. Pigment Red 177 and 12 g of disazo pigment of the formula (I) are mixed mechanically.
Die Pigmentzusammensetzung liefert im AM-Lack farbstarke Lackierungen mit rotstichig-orangem Farbton.The pigment composition in the AM varnish provides strong color varnishes with a reddish-orange hue.
Beispiel 2Example 2
90 g Natriumchlorid, 9 g C.l. Pigment Red 177, 6 g Disazopigment der Formel (I) und 17 ml Diethylenglykol werden 8 h bei 40°C geknetet. Die Knetmasse wird in90 g sodium chloride, 9 g C.I. Pigment Red 177, 6 g of disazo pigment of the formula (I) and 17 ml of diethylene glycol are kneaded at 40 ° C. for 8 h. The plasticine is in
200 ml wässriger Salzsäure 5 gew.-%ig 2 h bei 40°C gerührt, die Suspension wird filtriert, der Presskuchen salzfrei gewaschen und bei 80°C getrocknet.200 ml of aqueous 5% hydrochloric acid are stirred at 40 ° C. for 2 hours, the suspension is filtered, the presscake is washed free of salt and dried at 80 ° C.
Die Pigmentzusammensetzung liefert im AM-Lack farbstarke Lackierungen rotstichig-orangem und reinem Farbton. Der Vollton ist transparent. Beispiele 3 bis 8The pigment composition in the AM varnish provides strong paint finishes with a reddish-orange and pure color. The full tone is transparent. Examples 3 to 8
Folgende Mischungen wurden hergestellt:The following mixtures were made:
Im AM-Lack werden farbstarke Lackierungen erhalten mit orangen bis gelbstichigroten Farbtönen.In the AM lacquer, strong-colored lacquers are obtained with orange to yellowish red hues.
Beispiel 9Example 9
25 g C.l. Pigment Red 254, 4 g C.l. Pigment Red 177 und 1 g Disazopigment der25 g C.I. Pigment Red 254, 4 g C.I. Pigment Red 177 and 1 g of disazo pigment
Formel (I) werden mechanisch gemischt.Formula (I) are mixed mechanically.
Im AM-Lack werden farbstarke Lackierungen erhalten mit gelbstichig-rotemIn the AM varnish, strong color varnishes are obtained with yellowish red
Farbton und hohem Glanz, die Viskosität des Lacks ist niedrig.Color and high gloss, the viscosity of the paint is low.
Beispiel 10Example 10
90 g Natriumchlorid, 12,5 g C.l. Pigment Red 254, 2 g C.l. Pigment Red 177, 0,5 g Disazopigment der Formel (I) und 24,5 ml Diethylenglykol werden 8 h bei 40CC geknetet. Die Knetmasse wird in 200 ml wässriger Salzsäure (5 gew.-%ig) 2 h bei 40°C gerührt, die Suspension wird filtriert, der Presskuchen salzfrei gewaschen und bei 80°C getrocknet. Die Pigmentzusammensetzung liefert im AM-Lack farbstarke, transparente Lackierungen mit gelbstichig-rotem Farbton und hohem Glanz, die Viskosität des Lacks ist niedrig.90 g of sodium chloride, 12.5 g of Cl Pigment Red 254, 2 g of Cl Pigment Red 177, 0.5 g of disazo pigment of the formula (I) and 24.5 ml of diethylene glycol are kneaded at 40 ° C. for 8 hours. The modeling clay is stirred in 200 ml of aqueous hydrochloric acid (5% by weight) for 2 hours at 40 ° C., the suspension is filtered, the presscake is washed free of salt and dried at 80 ° C. The pigment composition in the AM lacquer provides strong, transparent lacquers with a yellowish-red hue and high gloss, the viscosity of the lacquer is low.
Beispiel 11a 450 g Natriumchlorid, 75 g Disazopigment der Formel (I), hergestellt gemäß DE 10045790 A1 Beispiel 2, und 110 ml Diethylenglykol werden 8 h bei 85°C geknetet. Die Knetmasse wird in 4 Liter wässriger Schwefelsäure 5 gew.-%ig 2 h bei 40°C gerührt, die Suspension wird filtriert, der Presskuchen salzfrei gewaschen und bei 80°C getrocknet. Es werden 74 g Disazopigment der Formel (I) erhalten.Example 11a 450 g of sodium chloride, 75 g of disazo pigment of the formula (I), prepared according to DE 10045790 A1 Example 2, and 110 ml of diethylene glycol are kneaded at 85 ° C. for 8 hours. The modeling clay is stirred in 4 liters of 5% strength by weight aqueous sulfuric acid at 40 ° C. for 2 hours, the suspension is filtered, the presscake is washed free of salt and dried at 80 ° C. 74 g of disazo pigment of the formula (I) are obtained.
Beispiel 11b 18 g C.l. Pigment Red 254 und 2 g Disazopigment der Formel (I), hergestellt gemäß Beispiel 11a, werden mechanisch gemischt.Example 11b 18 g C.I. Pigment Red 254 and 2 g of disazo pigment of the formula (I), prepared according to Example 11a, are mixed mechanically.
Beispiel 12 15 g C.l. Pigment Red 254, 3 g C.l. Pigment Red 264 und 2 g Disazopigment der Formel (I), hergestellt gemäß Beispiel 11a, werden mechanisch gemischt.Example 12 15 g C.I. Pigment Red 254, 3 g C.I. Pigment Red 264 and 2 g of disazo pigment of the formula (I), prepared according to Example 11a, are mixed mechanically.
Beispiel 13Example 13
90 g Natriumchlorid, 11,25 g C.l. Pigment Red 254, 2,25 g C.l. Pigment Red 264, 1 ,5 g Disazopigment der Formel (I), hergestellt gemäß Beispiel 11a, und 24 ml Diethylenglykol werden 6 h bei 40°C geknetet. Die Knetmasse wird in 500 ml wässriger Schwefelsäure (5 gew.-%ig) 2 h bei 40°C gerührt, die Suspension wird filtriert, der Presskuchen salzfrei gewaschen und bei 80°C getrocknet.90 g sodium chloride, 11.25 g C.I. Pigment Red 254, 2.25 g C.I. Pigment Red 264, 1.5 g of disazo pigment of the formula (I), prepared according to Example 11a, and 24 ml of diethylene glycol are kneaded at 40 ° C. for 6 h. The modeling clay is stirred in 500 ml of aqueous sulfuric acid (5% by weight) for 2 hours at 40 ° C., the suspension is filtered, the presscake is washed free of salt and dried at 80 ° C.
Prüfung für Color-FilterTesting for color filters
Herstellung eines Test-Color Filters: Es wird zunächst eine Color Filter-Paste hergestellt, die aus Pigmentzusammensetzung, Bindemittel, Lösemittel und Dispergierhilfsmittel nach folgender Rezeptur besteht: 77 Gew.-% 1-Methoxy-2-propylacetat 10 Gew.-% Styrolacrylpolymer 10 Gew.-% Pigmentzusammensetzung; und 3 Gew.-% Dispergierhilfsmittel. Die vorstehende Mischung wird mit Zirkonkugeln (0 0,5-0,7 mm) in einem Paint Shaker für 2 Stunden dispergiert. Die Dispersion wird anschließend filtriert. Die dabei erhaltene Color Filter-Paste wird auf ein Glassubstrat mittels Spin Coater aufgetragen, um einen Color Filter-Film zu erzeugen. Die Transparenz, coloristische Werte, Hitzestabilität und der Kontrast werden an diesem Color Filter- Film bestimmt.Production of a test color filter: First a color filter paste is produced, which consists of pigment composition, binder, solvent and dispersion aid according to the following recipe: 77% by weight 1-methoxy-2-propyl acetate 10% by weight styrene acrylic polymer 10% by weight pigment composition; and 3% by weight dispersing aid. The above mixture is dispersed with zircon balls (0 0.5-0.7 mm) in a paint shaker for 2 hours. The dispersion is then filtered. The color filter paste obtained is applied to a glass substrate using a spin coater to produce a color filter film. The transparency, coloristic values, heat stability and contrast are determined on this color filter film.
Die Transmission des beschichteten Glassubstrates wird spektrophotometrisch im Anwendungsbereich von 400 - 700 nm ermittelt. Die coloristischen Werte werden mit dem CIE Farbdreieck (xyY Werte) beschrieben: x beschreibt dabei die blau-rot Achse, y die blau-grün Achse, Y die Brillanz.The transmission of the coated glass substrate is determined spectrophotometrically in the application range from 400 to 700 nm. The coloristic values are described with the CIE color triangle (xyY values): x describes the blue-red axis, y the blue-green axis, Y the brilliance.
Die Viskosität wird an der oben beschriebenen Color Filter-Paste mit einem Rotationsviskosimeter bei einer Temperatur von 23°C ± 0,5°C und bei einer Schergeschwindigkeit von 60s"1 ermittelt.The viscosity is determined on the color filter paste described above using a rotary viscometer at a temperature of 23 ° C ± 0.5 ° C and at a shear rate of 60s "1 .
Die Hitzestabilität wird durch den delta E Wert beschrieben; der delta E Wert wird nach DIN 6174 bestimmt, er beschreibt den Gesamtfarbabstand und lässt sich aus den x, y, Y Werten errechnen. Das beschichtete Glassubstrat wird nach Messung der Transmission bei 80°C für 10min temperiert. Anschließend werden die Transmission gemessen und das delta E berechnet. Das beschichtete Glassubstrat wird nun bei 250°C für 1 h temperiert und wiederum ein delta E Wert ermittelt.The heat stability is described by the delta E value; The delta E value is determined according to DIN 6174, it describes the total color difference and can be calculated from the x, y, y values. After measuring the transmission, the coated glass substrate is tempered for 10 minutes at 80 ° C. The transmission is then measured and the delta E calculated. The coated glass substrate is then tempered at 250 ° C. for 1 h and again a delta E value is determined.
Außerdem wird mit der Color Filter-Paste eine Vollton-Lackierung und nach Verdünnen mit einer Weiß-Paste eine sogenannte Aufhellungslackierung durch Rakelung angefertigt, deren Coloristiken beurteilt werden. Prüfung für Color Filter mit der Pigmentzusammensetzung gemäß Beispiel 11b:In addition, the color filter paste is used to produce a full-tone coating and, after dilution with a white paste, a so-called brightening coating by knife coating, the color characteristics of which are assessed. Test for color filters with the pigment composition according to Example 11b:
Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: η = 12,8 mPa.s. Anschließend werden 3 ml von der Color Filter-Paste pipettiert und auf ein Glassubstrat mittels Spin Coater bei einer Drehgeschwindigkeit von 2500 rpm während 20s aufgetragen. Die coloristischen Eigenschaften des Color Filter-Films werden anschließend spektrophotometrisch bestimmt.A color filter paste is produced. The viscosity of the color filter paste is: η = 12.8 mPa.s. 3 ml of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a rotational speed of 2500 rpm for 20 s. The coloristic properties of the color filter film are then determined spectrophotometrically.
Coloristische Werte:Coloristic values:
Transmissionswerte:Transmission values:
Die Hitzestabilität ist gut.The heat stability is good.
Die Lackierungen zeigen hohe Transparenz und Farbstärke und einen reinen Farbton. Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: η - 23,2 mPa.s. Anschließend werden 3 ml von der Color Filter-Paste pipettiert und auf ein Glassubstrat mittels Spin Coater bei einer Drehgeschwindigkeit von 2500 rpm während 20s aufgetragen. Die coloristischen Eigenschaften des Color Filter-Films werden anschließend spektrophotometrisch bestimmt.The paintwork shows high transparency and color strength and a pure color. A color filter paste is produced. The viscosity of the color filter paste is: η - 23.2 mPa.s. 3 ml of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a rotational speed of 2500 rpm for 20 s. The coloristic properties of the color filter film are then determined spectrophotometrically.
Coloristische Werte:Coloristic values:
Transmissionswerte:Transmission values:
Die Hitzestabilität ist gut.The heat stability is good.
Die Lackierungen zeigen hohe Transparenz und Farbstärke und einen reinen Farbton.The paintwork shows high transparency and color strength and a pure color.
Prüfung für Color Filter mit der Pigmentzusammensetzung gemäß Beispiel 13: Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: 77 = 119,8 mPa.s. Anschließend werden 3 ml von der Color Filter-Paste pipettiert und auf ein Glassubstrat mittels Spin Coater bei einer Drehgeschwindigkeit von 2500 rpm während 20s aufgetragen. Die coloristischen Eigenschaften des Color Filter-Films werden anschließend spektrophotometrisch bestimmt.Test for color filters with the pigment composition according to Example 13: A color filter paste is produced. The viscosity of the color filter paste is: 77 = 119.8 mPa.s. 3 ml of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a rotational speed of 2500 rpm for 20 s. The coloristic properties of the color filter film are then determined spectrophotometrically.
Coloristische Werte:Coloristic values:
Transmissionswerte:Transmission values:
Die Hitzestabilität ist gut.The heat stability is good.
Die Lackierungen zeigen hohe Transparenz und Farbstärke und einen reinen Farbton. The paintwork shows high transparency and color strength and a pure color.

Claims

Patentansprüche: claims:
1) Pigmentzusammensetzung, enthaltend ein Disazopigment der Formel (I),1) pigment composition containing a disazo pigment of the formula (I),
und ein oder mehrere Pigmente aus der Gruppe der organischen Orange-, Rot- und Violetpigmente. and one or more pigments from the group of organic orange, red and violet pigments.
2) Pigmentzusammensetzung nach Anspruch 1 , dadurch gekennzeichnet, dass das organische Orangepigment C.l. Pigment Orange 5, 13, 14, 16, 34, 36, 38, 42, 43, 48, 49, 51, 61, 62, 64, 67, 68, 69, 71, 72, 73, 74; oder eine Kombination davon ist.2) Pigment composition according to claim 1, characterized in that the organic orange pigment C.I. Pigment Orange 5, 13, 14, 16, 34, 36, 38, 42, 43, 48, 49, 51, 61, 62, 64, 67, 68, 69, 71, 72, 73, 74; or a combination of these.
3) Pigmentzusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass das organische Rotpigment C.l. Pigment Red 1, 2, 3, 4, 5, 7, 9, 12, 14, 23, 38, 41, 42, 48, 48:1, 48:2, 48:3, 48:4, 48:5, 48:6, 49, 49:1, 51:1, 52:1, 52:2, 53, 53:1, 53:3, 57, 57:1, 57:2, 57:3, 58:2, 58:4, 63:1, 81, 81:1, 81:2, 81:3, 81:4, 81:5, 81:6, 88, 112, 122, 123, 144, 146, 148, 149, 150, 166, 168, 169, 170, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 192, 194, 200, 200:1, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 242, 246, 247, 251, 253, 254, 255, 256, 257, 260, 262, 264, 270, 272; oder eine Kombination davon ist.3) Pigment composition according to claim 1, characterized in that the organic red pigment C.I. Pigment Red 1, 2, 3, 4, 5, 7, 9, 12, 14, 23, 38, 41, 42, 48, 48: 1, 48: 2, 48: 3, 48: 4, 48: 5, 48: 6, 49, 49: 1, 51: 1, 52: 1, 52: 2, 53, 53: 1, 53: 3, 57, 57: 1, 57: 2, 57: 3, 58: 2, 58: 4, 63: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 81: 5, 81: 6, 88, 112, 122, 123, 144, 146, 148, 149, 150, 166, 168, 169, 170, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 192, 194, 200, 200: 1, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 242, 246, 247, 251, 253, 254, 255, 256, 257, 260, 262, 264, 270, 272; or a combination of these.
4) Pigmentzusammensetzung nach Anspruch 1, dadurch gekennzeichnet, dass das organische Violetpigment C.l. Pigment Violet 19 ist. 5) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass das Gewichtsverhältnis Disazopigment der Formel (I) zu organischem Orange-, Rot- oder Violetpigment (0,1 zu 99,9) bis (99,9 zu 0,1) beträgt.4) Pigment composition according to claim 1, characterized in that the organic violet pigment Cl Pigment Violet 19. 5) pigment composition according to at least one of claims 1 to 4, characterized in that the weight ratio of disazo pigment of formula (I) to organic orange, red or violet pigment (0.1 to 99.9) to (99.9 to 0, 1).
6) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das Gewichtsverhältnis Disazopigment der Formel (I) zu organischem Orange-, Rot- oder Violetpigment (10 zu 90) bis (90 zu 10) beträgt.6) Pigment composition according to at least one of claims 1 to 5, characterized in that the weight ratio of disazo pigment of formula (I) to organic orange, red or violet pigment (10 to 90) to (90 to 10).
7) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie eine feste Lösung oder Mischkristall ist.7) pigment composition according to at least one of claims 1 to 6, characterized in that it is a solid solution or mixed crystal.
8) Verfahren zur Herstellung einer Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 6 durch Vermischen des Disazopigments der Formel (I) mit dem oder den organischen Orange-, Rot- oder Violetpigmenten.8) Process for the preparation of a pigment composition according to at least one of claims 1 to 6 by mixing the disazo pigment of the formula (I) with the organic or orange, red or violet pigments.
9) Verwendung einer Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 7 zum Pigmentieren von hochmolekularen organischen Materialien, beispielsweise von Kunststoffen, Harzen, Lacken, Anstrichfarben, elektrophotographischen Tonern und Entwicklern, Elektretmaterialien, Farbfiltern sowie von Tinten, Ink-Jet-Tinten, Druckfarben und Saatgut.9) Use of a pigment composition according to at least one of claims 1 to 7 for pigmenting high molecular weight organic materials, for example plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and inks, ink-jet inks, printing inks and seed.
10) Hochmolekulares organisches Medium, enthaltend eine färberisch wirksame Menge einer Pigmentzusammensetzung nach einem oder mehreren der Ansprüche 1 bis 7. 10) high molecular weight organic medium containing a dye-effective amount of a pigment composition according to one or more of claims 1 to 7.
EP04797818A 2003-11-14 2004-11-11 Pigment compositions consisting of a yellow disazo pigment and an organic pigment Withdrawn EP1689817A1 (en)

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DE10353127A DE10353127A1 (en) 2003-11-14 2003-11-14 Pigment compositions of yellow disazo pigment and organic pigment
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US20070125263A1 (en) 2007-06-07
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US7311769B2 (en) 2007-12-25
CN100503737C (en) 2009-06-24
WO2005049737A1 (en) 2005-06-02
BRPI0416557A (en) 2007-01-23
CA2545210A1 (en) 2005-06-02
DE10353127A1 (en) 2005-06-09

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