EP1689818A1 - Compositions de pigments composees de pigment jaune organique et de pigment de phtalocyanine - Google Patents

Compositions de pigments composees de pigment jaune organique et de pigment de phtalocyanine

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Withdrawn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)
English (en)
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/fr
Withdrawn legal-status Critical Current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

L'invention concerne une composition de pigments contenant un pigment disazo représenté par la formule (I), et un ou plusieurs pigments de phtalocyanine.
EP04797819A 2003-11-14 2004-11-11 Compositions de pigments composees de pigment jaune organique et de pigment de phtalocyanine Withdrawn EP1689818A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10353126A DE10353126A1 (de) 2003-11-14 2003-11-14 Pigmentzusammensetzungen aus organischem Gelbpigment und Phthalocyaninpigment
PCT/EP2004/012789 WO2005049738A1 (fr) 2003-11-14 2004-11-11 Compositions de pigments composees de pigment jaune organique et de pigment de phtalocyanine

Publications (1)

Publication Number Publication Date
EP1689818A1 true EP1689818A1 (fr) 2006-08-16

Family

ID=34559636

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04797819A Withdrawn EP1689818A1 (fr) 2003-11-14 2004-11-11 Compositions de pigments composees de pigment jaune organique et de pigment de phtalocyanine

Country Status (9)

Country Link
US (1) US20090101874A1 (fr)
EP (1) EP1689818A1 (fr)
JP (1) JP2007517080A (fr)
KR (1) KR20060103507A (fr)
CN (1) CN100415834C (fr)
BR (1) BRPI0416569A (fr)
CA (1) CA2546483A1 (fr)
DE (1) DE10353126A1 (fr)
WO (1) WO2005049738A1 (fr)

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DE10353127A1 (de) * 2003-11-14 2005-06-09 Clariant Gmbh Pigmentzusammensetzungen aus gelbem Disazopigment und organischem Pigment
JP4849551B2 (ja) * 2007-01-15 2012-01-11 花王株式会社 イエロートナー及びマゼンタトナー
JP2009151162A (ja) * 2007-12-21 2009-07-09 Toyo Ink Mfg Co Ltd シアン顔料、その製造方法及び画像記録用着色組成物
JP4995334B2 (ja) * 2010-08-27 2012-08-08 キヤノン株式会社 アゾ化合物、該アゾ化合物を含有する顔料分散剤、顔料組成物、顔料分散体及びトナー
JP6011847B2 (ja) * 2012-07-24 2016-10-19 Dic株式会社 インクジェット記録用水性インク調製のための水性顔料分散体及びインクジェット記録水性インク
WO2018043160A1 (fr) * 2016-08-31 2018-03-08 日本ゼオン株式会社 Toner jaune
CN115772336B (zh) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 一种紫色有机颜料的制备
CN115785695B (zh) * 2022-11-15 2024-02-20 双乐颜料泰兴市有限公司 一种绿色有机颜料的制备

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Also Published As

Publication number Publication date
CN1878840A (zh) 2006-12-13
JP2007517080A (ja) 2007-06-28
WO2005049738A1 (fr) 2005-06-02
US20090101874A1 (en) 2009-04-23
CA2546483A1 (fr) 2005-06-02
BRPI0416569A (pt) 2007-01-23
KR20060103507A (ko) 2006-10-02
CN100415834C (zh) 2008-09-03
DE10353126A1 (de) 2005-06-09

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