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EP1689818A1 - Pigment compositions consisting of an organic yellow pigment and a phthalocyanine pigment - Google Patents

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

Info

Publication number
EP1689818A1
EP1689818A1 EP04797819A EP04797819A EP1689818A1 EP 1689818 A1 EP1689818 A1 EP 1689818A1 EP 04797819 A EP04797819 A EP 04797819A EP 04797819 A EP04797819 A EP 04797819A EP 1689818 A1 EP1689818 A1 EP 1689818A1
Authority
EP
European Patent Office
Prior art keywords
pigment
phthalocyanine
composition according
pigment composition
weight
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Withdrawn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
EP04797819A
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 EP1689818A1 publication Critical patent/EP1689818A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • 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
    • 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
    • G03G9/0918—Phthalocyanine dyes

Definitions

  • the invention relates to pigment compositions of an organic yellow pigment and phthalocyanine 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),
  • phthalocyanine pigments one or more, e.g. one, two or three, phthalocyanine pigments.
  • the phthalocyanine in the pigment composition according to the invention can be halogenated or halogen-free, metal-free or containing metal atoms.
  • Metals can be, for example, Cu, Fe, Co, Zn, Sn, Cd, Ni, Ti or Al, copper is preferred.
  • the phthalocyanine can be substituted with up to 16 halogen atoms, such as chlorine and bromine.
  • the phthalocyanines can be in different phases, for example alpha, beta, gamma, delta or epsilon.
  • copper phthalocyanines which are halogen-free or have only a low chlorine content, for example up to 6% by weight, ie 0 to 1 Cl atoms per phthalocyanine molecule
  • those in the beta phase are preferred.
  • Preferred copper phthalocyanines of the alpha phase are those with a chlorine content of 0 to 20% by weight, for example semichloro copper phthalocyanine, monochloro copper phthalocyanine or tri / tetrachloro copper phthalocyanine.
  • Pigment compositions containing one or two phthalocyanines from the group CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6 and 16 are preferred; Cl Pigment Green 7, 36 and 37, in particular Cl Pigment Blue 15: 3.
  • Pigment compositions according to the invention with yellowish-green shades preferably contain the Cl Pigment Green 36.
  • the disazo pigment and the phthalocyanine can form a common crystal lattice, for example in the form of solid solutions or mixed crystals.
  • pigment compositions according to the invention color shades from greenish yellow to green to greenish blue can be achieved. They are of particular interest for hues in the yellowish green area.
  • the weight ratio of disazo pigment of the formula (I) to phthalocyanine (0.1 to 99.9) to (99.9 to 0.1), preferably (1 to 99) to (99 to 1), is particularly preferred (5 to 95) to (95 to 5) and in particular (10 to 90) to (90 to 10).
  • 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.
  • the mixing can be carried out, for example, by acid pasting, acid swelling, by grinding 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.
  • Mixing can also be done by adding one component to the other component during the manufacturing process of one of the components.
  • the manufacturing process of a phthalocyanine in the sense of the invention comprises all steps after the actual chemical synthesis of the phthalocyanine ring system.
  • the disazo pigment can be added to the phthalocyanine as soon as the phthalocyanine ring system has formed chemically from the corresponding phthalic acid derivatives.
  • the crude phthalocyanine pigment usually obtained in the course of chemical synthesis is comminuted, for example by acid pasting, acid swelling, dry or wet grinding.
  • the finely crystalline phthalocyanines are usually subjected to an aftertreatment, generally referred to as a finish, for example in water and / or solvents and usually at elevated temperature and, if appropriate, increased pressure.
  • the manufacturing process of the disazo pigment comprises diazotizing the underlying aromatic amine to form the diazonium salt, optionally dissolving and possibly precipitating the underlying coupling component, mixing the two reactants diazonium salt and coupling component, the coupling component being able to be added to the diazonium salt or vice versa or also continuously 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 known drying units can be used for drying, such as drying cupboards, paddle wheel dryers, tumble dryers, contact dryers and in particular spin flash and spray dryers. By choosing 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.
  • a 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 sum of the weights of yellow pigment and phthalocyanine. In exceptional cases, however, higher quantities can also be used.
  • the auxiliaries and the shading colorants can be added 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 polyols, polyvinyl ether or polyvinyl
  • the present invention therefore also relates to a high molecular weight organic material containing a dye-effective amount of a pigment composition according to the invention.
  • the pigment composition according to the invention is usually used in an amount of 0.01 to 30% by weight, preferably 0.1 to 15% by weight.
  • 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% by weight, preferably 1.5 to 8% by weight, of one or more of the pigment compositions according to the invention, 5 to 99% by weight of water and 0.5 to 94.5% by weight.
  • Hot-melt 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 fatty acids, fatty alcohols or sulfonamides that are solid at room temperature and become liquid when heated, with the preferred melting range between approx. 60 ° C and approx. 140 ° C lies.
  • 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.
  • an additional polymer as a "dye dissolver"
  • dispersing aid 0 to 20% by weight of viscosity modifier
  • plasticizer 0 to 10% by weight % Stickiness additive
  • transparency stabilizer prevents, for example, crystallization of the waxes
  • antioxidant 0 to 2% by weight antioxidant
  • 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 ").
  • suitable binders acrylates, acrylic esters, polyimides, polyvinyl alcohols, epoxies, polyesters, melamines, gelatins, caseins
  • high pigment purity is also required for stable paste or pigmented photoresist
  • the pigmented color filters can also be applied using ink jet printing processes or other suitable printing processes
  • the pigment compositions according to the invention are notable for their outstanding coloristic and theological 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 concentrate.
  • 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-green 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.
  • 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 on the following five-point scale.
  • Example 1 10.5 g C.I. Pigment Green 36 and 4.5 g of disazo pigment of the formula (I) are mixed mechanically.
  • the pigment composition in the AM varnish provides strong color varnishes with a yellowish green hue.
  • Example 2 90 g sodium chloride, 10.5 g C.I. Pigment Green 36, 4.5 g of disazo pigment of the formula (I) and 15 ml of diethylene glycol are kneaded at 45 ° C. for 8 h.
  • the modeling clay is stirred in 150 ml of 5% strength by weight hydrochloric acid at 40 to 45 ° C. for 2 hours, the suspension is filtered, the presscake is washed salt-free and at
  • the pigment composition in the AM varnish provides strong color varnishes yellowish green and pure color.
  • the full tone is transparent.
  • Example 14b 450 g of sodium chloride, 75 g of disazo pigment of the formula (I), prepared in accordance with 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 14b 450 g of sodium chloride, 75 g of disazo pigment of the formula (I), prepared in accordance with 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
  • Example 15 15 g of disazo pigment of the formula (I), prepared in accordance with DE 100 45 790 A1
  • Example 2 and 15 g C.I. Pigment Green 36 are mixed mechanically.
  • a color filter paste which consists of pigment composition, binder, solvent and dispersing 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 of 400-700 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 hour 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.
  • Test for color filters with the pigment composition according to Example 13 A color filter paste is produced.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paints show high transparency, gloss and color strength and a pure color.
  • Test for color filters on the pigment composition according to Example 14b A color filter paste is produced.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paints show high transparency, gloss and color strength and a pure color.
  • Test for color filters with the pigment composition according to Example 15 A color filter paste is produced.
  • the coloristic properties of the color filter film are then determined spectrophotometrically.
  • the heat stability is good.
  • the paints show high transparency, gloss and color strength and a pure color.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)

Abstract

The invention relates to a pigment composition containing a disazo pigment of formula (I) and at least one phthalocyanine pigment.

Description

Pigmentzusammensetzungen aus organischem Gelbpigment und Phthalocyaninpigment Organic yellow pigment and phthalocyanine pigment compositions
Die Erfindung betrifft Pigmentzusammensetzungen aus einem organischen Gelbpigment und Phthalocyaninpigment und ihre Verwendung zum Färben von hochmolekularen Materialien.The invention relates to pigment compositions of an organic yellow pigment and phthalocyanine 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 Einsetzbarkeit 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 Einsetzbarkeit 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, the most universal applicability for dyeing other high molecular systems, such as plastics and printing inks, is desirable. 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. In the case of paints and printing inks, applicability 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 grünen 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 green 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, Phthalocyaninpigmente.and one or more, e.g. one, two or three, phthalocyanine pigments.
Das Phthalocyanin in der erfindungsgemäßen Pigmentzusammensetzung kann halogeniert oder halogenfrei, metallfrei oder metallatomhaltig sein. Metalle können beispielsweise Cu, Fe, Co, Zn, Sn, Cd, Ni, Ti oder AI sein, bevorzugt ist Kupfer. Das Phthalocyanin kann mit bis zu 16 Halogenatomen, wie beispielsweise Chlor und Brom, substituiert sein. Die Phthalocyanine können in unterschiedlicher Phase vorliegen, beispielsweise alpha, beta, gamma, delta oder epsilon. Im Falle der Kupferphthalocyanine, die halogenfrei sind oder einen nur geringen Chlorgehalt, beispielsweise bis 6 Gew.-%, d.h. 0 bis 1 Cl-Atome pro Phthalocyaninmolekül, aufweisen, sind solche in der beta-Phase bevorzugt. Als Kupferphthalocyanin der alpha-Phase sind solche mit einem Chlorgehalt von 0 bis zu 20 Gew.-% bevorzugt, beispielsweise Semichlorkupferphthalocyanin, Monochlorkupferphthalocyanin oder Tri-/ Tetrachlorkupferphthalocyanin. Bevorzugt sind Pigmentzusammensetzungen, enthaltend ein oder zwei Phthalocyanine aus der Gruppe C.l. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6 und 16; C.l. Pigment Green 7, 36 und 37, insbesondere C.l. Pigment Blue 15:3. Erfindungsgemäße Pigmentzusammensetzungen mit gelbstichig-grünen Farbtönen enthalten bevorzugt das C.l. Pigment Green 36.The phthalocyanine in the pigment composition according to the invention can be halogenated or halogen-free, metal-free or containing metal atoms. Metals can be, for example, Cu, Fe, Co, Zn, Sn, Cd, Ni, Ti or Al, copper is preferred. The phthalocyanine can be substituted with up to 16 halogen atoms, such as chlorine and bromine. The phthalocyanines can be in different phases, for example alpha, beta, gamma, delta or epsilon. In the case of copper phthalocyanines which are halogen-free or have only a low chlorine content, for example up to 6% by weight, ie 0 to 1 Cl atoms per phthalocyanine molecule, those in the beta phase are preferred. Preferred copper phthalocyanines of the alpha phase are those with a chlorine content of 0 to 20% by weight, for example semichloro copper phthalocyanine, monochloro copper phthalocyanine or tri / tetrachloro copper phthalocyanine. Pigment compositions containing one or two phthalocyanines from the group CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 5, 15: 6 and 16 are preferred; Cl Pigment Green 7, 36 and 37, in particular Cl Pigment Blue 15: 3. Pigment compositions according to the invention with yellowish-green shades preferably contain the Cl Pigment Green 36.
In den erfindungsgemäßen Pigmentzusammensetzungen kann das Disazopigment und das Phthalocyanin ein gemeinsames Kristallgitter ausbilden, beispielsweise in Form von festen Lösungen oder Mischkristallen.In the pigment compositions according to the invention, the disazo pigment and the phthalocyanine 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 grünstichigem Gelb über Grün zu grünstichigem Blau erzielen. Sie sind besonders für Farbtöne im gelbstichigen Grünbereich von Interesse.With the pigment compositions according to the invention, color shades from greenish yellow to green to greenish blue can be achieved. They are of particular interest for hues in the yellowish green area.
In den erfindungsgemäßen Pigmentzusammensetzungen kann das Gewichtsverhältnis Disazopigment der Formel (I) zu Phthalocyanin (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 phthalocyanine (0.1 to 99.9) to (99.9 to 0.1), preferably (1 to 99) to (99 to 1), is particularly preferred (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 durch 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. Das Mischen kann auch durch Zugabe der einen Komponente zur anderen Komponente während des Herstellungsprozess einer der Komponenten erfolgen.The mixing can be carried out, for example, by acid pasting, acid swelling, by grinding 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. Mixing can also be done by adding one component to the other component during the manufacturing process of one of the components.
Dabei umfasst der Herstellprozess eines Phthalocyanins im Sinne der Erfindung alle Schritte nach der eigentlichen chemischen Synthese des Phthalocyanin- Ringsystems. Die Zugabe des Disazopigments zum Phthalocyanin kann erfolgen, sobald das Phthalocyaninringsystem sich chemisch aus den entsprechenden Phthalsäurederivaten gebildet hat. Das bei der chemischen Synthese gewöhnlicherweise grobkristallin anfallende Phthalocyanin-Rohpigment wird zerkleinert, beispielsweise durch Acidpasting, Acidswelling, Trocken- oder Nassmahlung. Manche Phthalocyanine fallen bereits bei der Synthese in einer feinkristallinen Form an, beispielsweise C.l. Pigment Green 7 oder 36, so dass ein spezieller Zerkleinerungsschritt nicht notwendig ist. Die feinkristallinen Phthalocyanine 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.The manufacturing process of a phthalocyanine in the sense of the invention comprises all steps after the actual chemical synthesis of the phthalocyanine ring system. The disazo pigment can be added to the phthalocyanine as soon as the phthalocyanine ring system has formed chemically from the corresponding phthalic acid derivatives. The crude phthalocyanine pigment usually obtained in the course of chemical synthesis is comminuted, for example by acid pasting, acid swelling, dry or wet grinding. Some phthalocyanines already occur in the synthesis in a fine crystalline form, for example C.I. Pigment Green 7 or 36, so that a special shredding step is not necessary. The finely crystalline phthalocyanines are usually subjected to an aftertreatment, generally referred to as a finish, for example in water and / or solvents and usually at elevated temperature and, if appropriate, increased pressure.
Der Herstellprozess des Disazopigments 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. 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 manufacturing process of the disazo pigment comprises diazotizing the underlying aromatic amine to form the diazonium salt, optionally dissolving and possibly precipitating the underlying coupling component, mixing the two reactants diazonium salt and coupling component, the coupling component being able to be added to the diazonium salt or vice versa or also continuously 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 known drying units can be used for drying, such as drying cupboards, paddle wheel dryers, tumble dryers, contact dryers and in particular spin flash and spray dryers. 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. Ein bevorzugter 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. A 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 Summe der Gewichte von Gelbpigment und Phthalocyanin, eingesetzt. Es können jedoch in Ausnahmefällen auch höhere Mengen verwendet werden. 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 sum of the weights of yellow pigment and phthalocyanine. In exceptional cases, however, higher quantities can also be used. The auxiliaries and the shading colorants can be added 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.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 polyols, polyvinyl ether or polyvinyl acetates, 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 coal water Resin 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 as plastic masses, melts or in the form of Spinning solutions, dispersions, varnishes, paints or printing inks are available. 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.
Es ist auch möglich, die Pigmentzusammensetzung erst bei der Einarbeitung in das hochmolekulare organische Medium herzustellen. Gegenstand der vorliegenden Erfindung ist daher auch ein hochmolekulares organisches Material, enthaltend eine färberisch wirksame Menge einer erfindungsgemäßen Pigmentzusammensetzung. Bezogen auf das zu pigmentierende, hochmolekulare organische Material setzt man die erfindungsgemäße Pigmentzusammensetzung meist in einer Menge von 0,01 bis 30 Gew.-%, vorzugsweise 0,1 bis 15 Gew.-%, ein. Es ist in manchen Fällen auch möglich, anstelle einer gemahlenen und/oder gefinishten erfindungsgemäßen Pigmentzusammensetzung ein entsprechendes 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.It is also possible to prepare the pigment composition only when it is incorporated into the high-molecular organic medium. The present invention therefore also relates to a high molecular weight organic material containing a dye-effective amount of a pigment composition according to the invention. Based on the high-molecular organic material to be pigmented, the pigment composition according to the invention is usually used in an amount of 0.01 to 30% by weight, preferably 0.1 to 15% by weight. In some cases it is also possible to use a corresponding crude with a BET surface area of greater than 2 m 2 / g, preferably greater than 5 m 2 / g, instead of a ground and / or finished pigment composition according to the invention. 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.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.
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. 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.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. 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 aufwachsen, 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% by weight, preferably 1.5 to 8% by weight, of one or more of the pigment compositions according to the invention, 5 to 99% by weight of water and 0.5 to 94.5% by weight. -% 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 fatty acids, fatty alcohols or sulfonamides that are solid at room temperature and become liquid when heated, with the preferred melting range between approx. 60 ° C and approx. 140 ° C lies. 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, high pigment purity is also required for stable paste or pigmented photoresist The pigmented color filters can also be applied using ink jet printing processes or other suitable printing processes.
Die erfindungsgemäßen Pigmentzusammensetzungen zeichnen sich aus durch ihre hervorragenden coloristischen und Theologischen 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 gelbstichig-grünen 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 theological 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 concentrate. 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-green 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 on the following five-point scale.
5 dünnflüssig5 thin
4 flüssig4 liquid
3 dickflüssig leicht gestockt3 viscous, slightly stocked
1 gestockt 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.1 stocked 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 10045 790 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 10045 790 A1 Example 2.
Beispiel 1 10,5 g C.l. Pigment Green 36 und 4,5 g Disazopigment der Formel (I) werden mechanisch gemischt. Die Pigmentzusammensetzung liefert im AM-Lack farbstarke Lackierungen mit gelbstichig-grünem Farbton.Example 1 10.5 g C.I. Pigment Green 36 and 4.5 g of disazo pigment of the formula (I) are mixed mechanically. The pigment composition in the AM varnish provides strong color varnishes with a yellowish green hue.
Beispiel 2 90 g Natriumchlorid, 10,5 g C.l. Pigment Green 36, 4,5 g Disazopigment der Formel (I) und 15 ml Diethylenglykol werden 8 h bei 45°C geknetet. Die Knetmasse wird in 150 ml wässriger Salzsäure 5 gew.-%ig 2 h bei 40 bis 45°C gerührt, die Suspension wird filtriert, der Presskuchen salzfrei gewaschen und beiExample 2 90 g sodium chloride, 10.5 g C.I. Pigment Green 36, 4.5 g of disazo pigment of the formula (I) and 15 ml of diethylene glycol are kneaded at 45 ° C. for 8 h. The modeling clay is stirred in 150 ml of 5% strength by weight hydrochloric acid at 40 to 45 ° C. for 2 hours, the suspension is filtered, the presscake is washed salt-free and at
80°C getrocknet.80 ° C dried.
Die Pigmentzusammensetzung liefert im AM-Lack farbstarke Lackierungen gelbstichig-grünem und reinem Farbton. Der Vollton ist transparent.The pigment composition in the AM varnish provides strong color varnishes yellowish green and pure color. The full tone is transparent.
Beispiele 3 bis 12Examples 3 to 12
Folgende mechanische Mischungen wurden hergestellt:The following mechanical mixtures were produced:
Im AM-Lack werden farbstarke Lackierungen erhalten mit grünen bis gelbstichiggrünen, reinen Farbtönen, hohem Glanz und niedriger Viskosität, die Wetterechtheit ist sehr gut.In the AM varnish, strong paint finishes are obtained with green to yellowish green, pure shades, high gloss and low viscosity, the weather fastness is very good.
Beispiel 13Example 13
450 g Natriumchlorid, 37,5 g Disazopigment der Formel (I), 37,5 g C.l. Pigment Green 36 und 130 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.450 g sodium chloride, 37.5 g disazo pigment of formula (I), 37.5 g C.I. Pigment Green 36 and 130 ml diethylene glycol are kneaded at 85 ° C for 8 h. 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.
Beispiel 14aExample 14a
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. Beispiel 14b450 g of sodium chloride, 75 g of disazo pigment of the formula (I), prepared in accordance with 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 14b
62,5 g C.l. Pigment Green 36 und 62,5 g Disazopigment der Formel (I), hergestellt gemäß Beispiel 14a, werden mechanisch gemischt.62.5 g C.I. Pigment Green 36 and 62.5 g of disazo pigment of the formula (I), prepared according to Example 14a, are mixed mechanically.
Beispiel 15 15 g Disazopigment der Formel (I), hergestellt gemäß DE 100 45 790 A1Example 15 15 g of disazo pigment of the formula (I), prepared in accordance with DE 100 45 790 A1
Beispiel 2, und 15 g C.l. Pigment Green 36 werden mechanisch gemischt.Example 2, and 15 g C.I. Pigment Green 36 are mixed mechanically.
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.Production of a test color filter: First a color filter paste is produced, which consists of pigment composition, binder, solvent and dispersing 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.
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.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 of 400-700 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. 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 1h temperiert und wiederum ein delta E Wert 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 . 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 hour 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.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.
Prüfung für Color Filter mit der Pigmentzusammensetzung gemäß Beispiel 13: Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: η = 106,1 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: η = 106.1 mPa.s. 3 mL of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a 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, Glanz und Farbstärke und einen reinen Farbton.The paints show high transparency, gloss and color strength and a pure color.
Prüfung für Color Filter von der Pigmentzusammensetzung gemäß Beispiel 14b: Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: η = 78,5mPa.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 on the pigment composition according to Example 14b: A color filter paste is produced. The viscosity of the color filter paste is: η = 78.5mPa.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, Glanz und Farbstärke und einen reinen Farbton.The paints show high transparency, gloss and color strength and a pure color.
Prüfung für Color Filter mit der Pigmentzusammensetzung gemäß Beispiel 15: Es wird eine Color Filter-Paste hergestellt. Die Viskosität der Color Filter-Paste beträgt: η = 18,5mPa.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 15: A color filter paste is produced. The viscosity of the color filter paste is: η = 18.5 mPa.s. 3 mL of the color filter paste are then pipetted and applied to a glass substrate using a spin coater at a 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, Glanz und Farbstärke und einen reinen Farbton. The paints show high transparency, gloss 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 Phthalocyaninpigmente.and one or more phthalocyanine pigments.
2) Pigmentzusammensetzung nach Anspruch 1 , dadurch gekennzeichnet, dass das Phthalocyaninpigment ein Cu-, Fe-, Co-, Zn-, Sn-, Cd-, Ni-, Ti- oder Al- Phthalocyaninpigment ist.2) Pigment composition according to claim 1, characterized in that the phthalocyanine pigment is a Cu, Fe, Co, Zn, Sn, Cd, Ni, Ti or Al phthalocyanine pigment.
3) Pigmentzusammensetzung nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass das Phthalocyaninpigment 0 bis 16 Halogenatome, bevorzugt Chlor und/oder Brom, enthält.3) Pigment composition according to claim 1 or 2, characterized in that the phthalocyanine pigment contains 0 to 16 halogen atoms, preferably chlorine and / or bromine.
4) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das Phthalocyaninpigment ein Cu- Phthalocyaninpigment in der beta-Phase mit 0 bis 1 Chloratomen ist.4) Pigment composition according to at least one of claims 1 to 3, characterized in that the phthalocyanine pigment is a Cu phthalocyanine pigment in the beta phase with 0 to 1 chlorine atoms.
5) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das Phthalocyaninpigment ein Cu- Phthalocyaninpigment in der alpha-Phase mit 0 bis 4 Chloratomen ist.5) pigment composition according to at least one of claims 1 to 3, characterized in that the phthalocyanine pigment is a Cu phthalocyanine pigment in the alpha phase with 0 to 4 chlorine atoms.
6) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass das Phthalocyaninpigment C.l. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16; C.l. Pigment Green 7, 36 oder 37, oder eine Kombination davon ist.6) pigment composition according to at least one of claims 1 to 5, characterized in that the phthalocyanine pigment Cl Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16; Cl Pigment Green 7, 36 or 37, or a combination thereof.
7) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass das Gewichtsverhältnis Disazopigment zu Phthalocyaninpigment (0,1 zu 99,9) bis (99,9 zu 0,1) ist.7) pigment composition according to at least one of claims 1 to 6, characterized in that the weight ratio of disazo pigment to phthalocyanine pigment (0.1 to 99.9) to (99.9 to 0.1).
8) Pigmentzusammensetzung nach mindestens einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass sie eine feste Lösung oder Mischkristall ist.8) pigment composition according to at least one of claims 1 to 7, characterized in that it is a solid solution or mixed crystal.
9) Verfahren zur Herstellung einer Pigmentzusammensetzung nach einem oder mehreren der Ansprüche 1 bis 7 durch Vermischen des Disazopigments mit dem oder den Phthalocyaninpigmenten.9) Method for producing a pigment composition according to one or more of claims 1 to 7 by mixing the disazo pigment with the phthalocyanine pigment or pigments.
10) Verwendung einer Pigmentzusammensetzung nach einem oder mehreren der Ansprüche 1 bis 8 zum Pigmentieren von hochmolekularen organischen Materialien natürlicher oder synthetischer Herkunft, beispielsweise von Kunststoffen, Harzen, Lacken, Anstrichfarben, elektrophotographischen Tonern und Entwicklern, Elektretmaterialien, Farbfiltern sowie von Tinten, Ink-Jet-Tinten, Druckfarben und Saatgut.10) Use of a pigment composition according to one or more of claims 1 to 8 for pigmenting high molecular weight organic materials of natural or synthetic origin, for example of plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and inks, ink-jet - inks, inks and seeds.
11 ) Hochmolekulares organisches Medium, enthaltend eine färberisch wirksame Menge einer Pigmentzusammensetzung nach einem oder mehreren der Ansprüche 1 bis 8. 11) High molecular weight organic medium containing a dye-effective amount of a pigment composition according to one or more of claims 1 to 8.
EP04797819A 2003-11-14 2004-11-11 Pigment compositions consisting of an organic yellow pigment and a phthalocyanine pigment Withdrawn EP1689818A1 (en)

Applications Claiming Priority (2)

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DE10353126A DE10353126A1 (en) 2003-11-14 2003-11-14 Pigment compositions of yellow organic pigment and phthalocyanine pigment
PCT/EP2004/012789 WO2005049738A1 (en) 2003-11-14 2004-11-11 Pigment compositions consisting of an organic yellow pigment and a phthalocyanine pigment

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CN (1) CN100415834C (en)
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CA (1) CA2546483A1 (en)
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Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10353127A1 (en) * 2003-11-14 2005-06-09 Clariant Gmbh Pigment compositions of yellow disazo pigment and organic pigment
JP4849551B2 (en) * 2007-01-15 2012-01-11 花王株式会社 Yellow toner and magenta toner
JP2009151162A (en) * 2007-12-21 2009-07-09 Toyo Ink Mfg Co Ltd Cyan pigment, method for producing the same, and coloring composition for image recording
JP4995334B2 (en) * 2010-08-27 2012-08-08 キヤノン株式会社 Azo compound, pigment dispersant, pigment composition, pigment dispersion and toner containing the azo compound
JP6011847B2 (en) * 2012-07-24 2016-10-19 Dic株式会社 Aqueous pigment dispersion for preparing water-based ink for ink-jet recording and water-based ink for ink-jet recording
US10520842B2 (en) * 2016-08-31 2019-12-31 Zeon Corporation Yellow toner
CN115772336B (en) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 Preparation of purple organic pigment
CN115785695B (en) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 Preparation of green organic pigment
CN117757307A (en) * 2023-12-29 2024-03-26 湖南松井先进表面处理与功能涂层研究院有限公司 A kind of water-based green slurry and preparation method thereof

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE759771A (en) * 1969-12-03 1971-05-17 Sandoz Sa LOW SOLUBLE AZOIC DYES
US4070353A (en) * 1973-04-18 1978-01-24 Ciba-Geigy Corporation Dicarboxylic acid ester diazo pigments
JPH0654397B2 (en) * 1985-09-03 1994-07-20 株式会社リコー Toner for electrostatic image development
JPS62280779A (en) * 1986-05-30 1987-12-05 Fuji Xerox Co Ltd Color developing method
JPS6346472A (en) * 1986-08-13 1988-02-27 Minolta Camera Co Ltd Positively electrifiable green toner
DE4229207C2 (en) * 1992-09-02 1998-12-17 Clariant Gmbh Process for the preparation of disazo pigments and their use
EP0822235B1 (en) * 1996-07-31 2002-01-30 Ciba SC Holding AG Process for the manufacture of disazo pigment mixtures with a high tinctorial power
JP2000063699A (en) * 1998-08-25 2000-02-29 Dainippon Ink & Chem Inc Pigment composition and resin coloring composition
DE10045790A1 (en) * 2000-09-15 2002-03-28 Clariant Gmbh New crystalline modifications of a yellow disazo colorant and process for their preparation
JP3379945B2 (en) * 2000-12-28 2003-02-24 日本ピグメント株式会社 Polyethylene terephthalate resin coloring composition
JP2003232914A (en) * 2002-02-13 2003-08-22 Sumitomo Chem Co Ltd Coloring composition and color filter using the same
DE10342601A1 (en) * 2003-09-12 2005-04-21 Clariant Gmbh Pigment compositions of organic and inorganic pigments
DE10351580A1 (en) * 2003-11-05 2005-06-02 Clariant Gmbh Green pigment preparations
DE10353127A1 (en) * 2003-11-14 2005-06-09 Clariant Gmbh Pigment compositions of yellow disazo pigment and organic pigment

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005049738A1 *

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WO2005049738A1 (en) 2005-06-02
CA2546483A1 (en) 2005-06-02
US20090101874A1 (en) 2009-04-23
BRPI0416569A (en) 2007-01-23
DE10353126A1 (en) 2005-06-09
CN100415834C (en) 2008-09-03
CN1878840A (en) 2006-12-13
JP2007517080A (en) 2007-06-28

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