Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
  • C08K5/23—Azo-compounds
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
  • C09D7/40—Additives
  • C09D7/41—Organic pigments; Organic dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G9/00—Developers
  • G03G9/08—Developers with toner particles
  • G03G9/09—Colouring agents for toner particles
  • G03G9/0906—Organic dyes
  • G03G9/091—Azo dyes
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
  • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices

Definitions

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

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Wood Science & Technology (AREA)
• Materials Engineering (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Paints Or Removers (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2003
  • 2003-11-14 DE DE10353127A patent/DE10353127A1/de not_active Withdrawn
• 2004
  • 2004-11-11 CA CA002545210A patent/CA2545210A1/en not_active Abandoned
  • 2004-11-11 EP EP04797818A patent/EP1689817A1/de not_active Withdrawn
  • 2004-11-11 BR BRPI0416557-8A patent/BRPI0416557A/pt not_active IP Right Cessation
  • 2004-11-11 US US10/579,344 patent/US7311769B2/en not_active Expired - Fee Related
  • 2004-11-11 WO PCT/EP2004/012788 patent/WO2005049737A1/de active Application Filing
  • 2004-11-11 JP JP2006538794A patent/JP2007514804A/ja active Pending
  • 2004-11-11 KR KR1020067009291A patent/KR20060109466A/ko not_active Application Discontinuation
  • 2004-11-11 CN CNB2004800334384A patent/CN100503737C/zh not_active Expired - Fee Related

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