EP0993489A1 - Dispersions pigmentaires contenant le pigment c.i. rouge 222 - Google Patents

Dispersions pigmentaires contenant le pigment c.i. rouge 222

Info

Publication number
EP0993489A1
EP0993489A1 EP98936394A EP98936394A EP0993489A1 EP 0993489 A1 EP0993489 A1 EP 0993489A1 EP 98936394 A EP98936394 A EP 98936394A EP 98936394 A EP98936394 A EP 98936394A EP 0993489 A1 EP0993489 A1 EP 0993489A1
Authority
EP
European Patent Office
Prior art keywords
compound
printing
pigment
solvent
pigment dispersion
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Withdrawn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
EP98936394A
Other languages
German (de)
English (en)
Inventor
Véronique Hall-Goulle
Yves Grandidier
Hanspeter Hauser
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of EP0993489A1 publication Critical patent/EP0993489A1/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Withdrawn legal-status Critical Current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
    • C09B67/006—Preparation of organic pigments
    • 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
    • G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
    • G03F1/54—Absorbers, e.g. of opaque materials
    • G03F1/56—Organic absorbers, e.g. of photo-resists
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
    • C09B29/33—Aceto- or benzoylacetylarylides
    • C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
    • C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/035—Disazo dyes characterised by two coupling components of the same type in which the coupling component containing an activated methylene group
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo 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
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to pigment dispersions containing a compound of the formula (I)
  • compound (I) for pigmenting high molecular weight material such as inks, toners, varnishes, color filters and cosmetics.
  • the compound of formula (I) is known and has the Coulor Index, CI. Pigment Red 222 and the chemical name N- [4- (benzoylamino) phenyl] -3-hydroxy-4 - [[2-methoxy-5- [[[3- (trifluromethyl) phenyl] carbonyl] amino] phenyl] azo] -2-naphthalene carboxamide.
  • Pigment Red 222 in a composition with two other pigments, CI. Pigment Red 149, CI. Pigment Red 53: 1, CI. Pigment Red 48: 1 or CI.
  • Pigment Red 177 for the production of a red toner for red ink pads and red pens is known from JP-59,219,756.
  • the pigments should have pure, strong and brilliant shades that make it possible to open up a large color space. Furthermore, they should be able to be used as a single pigment as well as a combination element in, for example, trichromatic pigments. Of particular interest are blue-tinged red pigments, in particular pigments that have a magenta shade and are highly transparent and also heat-resistant.
  • the pigment in terms of application technology, it proves to be advantageous to apply the pigment as a dispersion, since complex mixing and grinding operations which place an additional hygienic burden on the can be avoided.
  • dispersions improve the reproducibility of the pigmentation process, since the pigment particles are generally more homogeneously distributed than in the powder form. For economic reasons, it is particularly desirable to use concentrated, stable dispersions which require little space during transport or storage and at the same time have good stability.
  • the object of the present invention was therefore to provide a pigment dispersion comprising a pigment with a magenta shade which corresponds to the high application and color requirements and a process for the preparation of this pigment dispersion. Furthermore, the object of the invention was to provide a pigment with a magenta shade which can be used for the production of inks, toners, color filters or pigmented plastics.
  • the present invention accordingly relates to pigment dispersions containing
  • the pigment dispersions produced by the process according to the invention preferably have an average particle size distribution of 0.015-0.5 micrometers, particularly preferably 0.03-0.3 micrometers and very particularly preferably 0.05-0.2 micrometers.
  • the particle size distribution was determined using the disc centrifugation method according to Joyce-Loebl.
  • the pigment content of the pigment dispersions according to the invention is preferably in the range from 0.01 to 10% by weight, preferably in the range from 0.1 to 5% by weight, based on the total weight of the dispersion.
  • the solvent is used in 50 to 99.99% by weight, preferably 80 to 99.99% by weight, based on the total weight of pigment and polymer.
  • the polymer content of the pigment dispersions according to the invention is expediently in the range from 0.01 to 10% by weight, preferably in the range from 0.1 to 5% by weight, based on the total weight of the dispersion, the% details being 100% complementary .
  • solvent is water-based solvent, which may contain organic solvent or non-water-containing organic solvent and / or solvent mixtures thereof.
  • non-water-containing organic solvents are polar, aprotic solvents.
  • aliphatic C-Cr alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, and also polyols, cellosolves and carbitols such as ethylene glycol, diethylene glycol, triethylene glycol, glycerol, propylene glycol, diacetone alcohols such as 4-hydroxy are suitable -4-methyl-2-pentanone or ether alcohols such as bis (2-hydroxyethyl) ether, bis (2-hydroxyproplyl) ether or bis (2-hydroxybutyl) ether, ethylene glycol monomethyl or monoethyl ether, propylene glycol methyl ether, Dipropylene glycol methyl ether, tripropylene glycol methyl ether, ethylene glycol phenyl ether, propylene glycol monomethyl or monoethy
  • Aqueous solvents usually consist of water or mixtures of water and a non-aqueous organic solvent.
  • the pigment dispersions containing water-containing solvents are adjusted to a pH> 7, particularly preferably to a pH> 8.
  • the pH can be adjusted by mixing the water-containing mixture containing pigment, polymer and water with a base, or by mixing with a water-containing solution containing a base.
  • Organic or inorganic bases can be used as bases.
  • the organic bases used are preferably hydroxides of organic cations such as trimethylammonium or triethylammonium or amines such as mono-, di- or tri-methylamine, mono-, di- or tri-ethylamine or
  • Lithium, potassium or sodium hydroxide are preferably used as inorganic bases. Dimethylaminoethanol or morpholine are particularly preferred.
  • the pigment dispersions according to the invention can also contain compound (I) in colloidal form, in particular colloidal, embedded and / or dissolved in the polymer and / or solvent.
  • the present invention therefore further relates to pigment dispersions containing compound (I) in colloidal form.
  • the present invention preferably relates to a pigment dispersion comprising
  • the present invention relates to hydrous
  • the pigment dispersions according to the invention are prepared in accordance with the process according to the invention described below, or can be prepared from the corresponding pigments in the presence of grinding or grinding techniques using generally known processes of the prior art as described in US Pat. Nos. 4,597,794, 5,085,698, 5,030,669 or WO 96/14925 of polymers and solvents.
  • polymer also includes copolymer.
  • a polymer consisting of a hydrophilic and hydrophobic part is preferably used as the polymer for water-containing pigment dispersions.
  • the former part can be ionizable and form salts or be non-ionizable.
  • the polymer is preferably a random, block or graft polymer.
  • the hydrophilic part of the polymers is preferably composed, for example, of monomers which, in addition to functional groups such as, for example, alcohol, carboxylic acid, carboxamide, carboxylic ester or sulfonic acid groups, sulfate, cyanate or carboxylic anhydride, or ether groups such as ethylene or Propylene oxide groups and in addition a polymerizable vinyl or vinylene residue such as an acrylic, or methyl-acrylic, crotyl, sulfoethylmethylacryl, sulfopropylmethylacryl, vinylnaphthyl, vinylphenyl, vinyltolyl residue and an itaconyl residue such as, for example, itaconyl monoester, maleic acid or a maleinyl residue such as Examples include maleic acid monoesters, a fumaryl radical such as, for example, fumaryl monoesters and in particular vinylbenzoic acid.
  • the monoesters are preferably monoesters of itaconyl
  • Monomers are preferred which have carboxyl, carboxylic anhydride, sulfonate or sulfate groups as functional groups.
  • Carboxyl or carboxylic anhydride groups such as vinylbenzoic acid or maleic anhydride are particularly preferred.
  • Monomers which form the hydrophobic part of the polymers are preferably selected from the group of non-polar monomers consisting of styrene, styrene derivatives, such as CC 4 alkyl-substituted styrene, and vinyl chloride, vinyl naphthalene, vinyl naphthalene derivatives, such as C 1 -C 4 alkyl-substituted vinyl naphthalene, vinyl toluene, ⁇ , m, p or m, p vinyl toluene and aliphatic, C 12 -C 18 alkenes.
  • the preferred hydrophobic non-polar monomers are, for example, styrene, vinyl toluene and octadecene.
  • copolymers with a narrow molar mass distribution in the range of 1-2 Mw / Mn (in which Mw is mean mass and Mn is mean number).
  • the molar mass (number average) of the copolymers is preferably ⁇ 100000 g / mol.
  • Copolymers consisting, for example, of styrene, vinyltoluene and vinylbenzoic acid monomers preferably have a molecular weight of 10000-30000 g / mol, particularly preferably 15000-20000 g / mol and very particularly preferably 10000-15000 g / mol.
  • a further preferred embodiment of the invention relates to copolymers which are produced, for example, from styrene and maleic anhydride monomers, preferably have a molar mass of 500-5000 g / mol, particularly preferably 1000-3000 g / mol and very particularly preferably 500- 1500 g / mol.
  • Acrylate, methacrylate, styrene and vinyl polymers are usually used for non-aqueous pigment dispersions.
  • Another particularly preferred embodiment of the invention relates to pigment dispersions containing ethanol, polyvinyl butyrate and, for dispersions with methyl ethyl ketone as solvent, methyl methacrylate or for pigment dispersion with chloroform as solvent, copolymers of methyl methacrylate and butyl acrylate.
  • Preferred polymers for water-containing pigment dispersion can be composed, for example, of polymers containing carboxyl groups, such as, for example, styrene, vinyltoluene and vinylbenzoic acid or vinylbenzoic acid and nonpolar monomers, and of styrene and Maleic anhydride or from copolymers of long-chain alkenes (C ⁇ 2 -C ⁇ 8 ) with maleic anhydride such as styrene-maleic anhydride, styrene-vinyltoluene-vinylbenzoic acid or octadecene-maleic anhydride.
  • polymers containing carboxyl groups such as, for example, styrene, vinyltoluene and vinylbenzoic acid or vinylbenzoic acid and nonpolar monomers
  • styrene and Maleic anhydride or from copolymers of long-chain alkenes (C ⁇ 2 -C ⁇ 8 ) with maleic
  • a preferred embodiment of the process according to the invention relates to the preparation of water-containing basic pigment dispersions from the compound (I) with a solution of a copolymer containing vinylbenzoic acid and a non-polar monomer or with a solution containing a carboxyl-containing polymer.
  • the polymers for water-containing or non-water-containing pigment dispersions are commercially available, such as from the company, Scientific Polymer Products Inc., or can be prepared by known methods, for example as described in US Pat given in Example 1, by radical polymerization of the monomers, in the presence of a radical initiator such as 4,4'-azobis (4-cyanopentanoic acid) and a radical transfer agent such as dodecyl mercaptan.
  • a radical initiator such as 4,4'-azobis (4-cyanopentanoic acid)
  • a radical transfer agent such as dodecyl mercaptan.
  • the monomers and polymerization or copolymerization aids such as free radical initiators or free radical transfer agents and solvents, are commercially available products and can be obtained, for example, from Fluka.
  • the pigment dispersion according to the invention can additionally contain additives, such as surface-active compounds, which have a preferred spatial orientation in solvents.
  • additives and surfactant compounds of aqueous pigment dispersions are large molecules that consist of a hydrophilic head and a hydrophobic tail, such as Fluorad FC-170, a non-ionic fluorine-containing surfactant, from 3 M Inc. (or as OLOA TM 1200 from Chevron Corp., Richfield, CA, Amoco TM 9250, from Amoco Chemical Co., Naperville, IL).
  • the pigment dispersions obtained preferably have ⁇ 20% by weight, particularly preferably ⁇ 10% by weight and very particularly preferably ⁇ 5% by weight of additives, based on the total weight of the pigment dispersion and, if desired, can also comprise further cosolvents, such as cyclohexanone, cyclopentanone, N, N'-dimethylformamide or dimethyl sulfoxide. Furthermore, the present invention relates to a process for the preparation of the pigment dispersions according to the invention by
  • the dispersions according to the invention are prepared by successive or simultaneous addition of the four starting materials, compound (I), a salt, a polymer and solvent, the order of addition generally not being important.
  • the polymer is preferably initially introduced in the solvent and the pigment and salt are added, if desired in the presence of a solvent.
  • the polymer is particularly preferably added only before grinding.
  • the salt used is usually an alkali metal or ammonium halide, such as sodium, potassium, lithium or ammonium chloride, or sodium, potassium, lithium or ammonium bromide.
  • the molar ratio of compound (I) to the salt is usually in the range from 1:10 to 10: 1, particularly preferably in the range from 8: 3 to 3: 8.
  • the molar ratio of solvent to compound (I) and salt is preferably in the range from 1:50 to 50: 1, particularly preferably in the range from 1:20 to 20: 1.
  • the molar ratio of polymer to compound (I), solvent and salt is advantageously in the range from 1:50 to 50: 1, particularly preferably in the range from 1:20 to 20: 1.
  • the starting compounds are added by mixing analogously to known methods of mixing, such as by stirring with stirring apparatus, kneading in kneaders or extruding. Kneaders are preferred.
  • the mixing time is generally dependent on the desired batch size, the starting materials used (solvent, salt, polymer) and is generally in the range from 5 to 20 hours. Usually one works in a temperature range from 20 to 100 ° C, preferably in the temperature range from 40 to 80 ° C
  • the mixture comprising compound (I), polymer, salt and solvent is generally ground in known mixing apparatuses, such as in ball or bead mills.
  • Spheres such as glass spheres with a diameter in the range from 1 to 5 mm are preferably added to the grinding in ball mills or zirconium oxide spheres with a diameter in the range from 1 to 1.6 mm are added to the grinding in bead mills.
  • the grinding process generally takes 5 to 30 hours and preferably 15 to 25 hours, depending on the batch size in a ball mill. In a bead mill, the grinding process can take, for example, 1 minute to 1 hour and preferably 5 to 30 minutes.
  • the starting compounds (compound (I), salt and solvent) are mixed by the method described above and in the molar ratios given above.
  • the mixture obtained is usually filtered and then preferably washed with water until the salt or solvent content is below a desired limit.
  • the filter residue is usually provided with a polymer and solvent and then ground as described above.
  • the molar ratio of the compound (I) of the filter residue to the polymer is generally in the range from 20: 1 to 1:20 and preferably in the range from 10: 1 to 1:10.
  • the molar ratio of the compound (I) of the filter residue to the solvent is generally in the range from 50: 1 to 1:50, particularly preferably in the range from 20: 1 to 1:20 and very particularly preferably in the range from 1: 5 to 5: 1.
  • the filter residue can be dried in the temperature range from 40 to 120 ° C., preferably in the range from 50 to 100 ° C.
  • Suitable drying devices are, for example, drying cupboards or paddle dryers. After drying, the dried filter residue is usually provided with a polymer and solvent and the mixture obtained is then ground as described above.
  • the molar ratio of compound (I) of the mixture comprising compound (I), solvent and polymer to the polymer is generally in the range from 20: 1 to 1:20 and preferably in the range from 10: 1 to 1:10.
  • the molar ratio of compound (I) of the mixture comprising compound (I), solvent and polymer of the filter residue, to the solvent is generally in the range from 1:50 to 50: 1 and particularly preferably in the range from 20: 1 to 1:20 and preferably in the range and very particularly preferably in the range from 1: 5 to 5: 1.
  • a water-containing pigment dispersion is prepared by adjusting a water-containing solvent containing a base, in particular an organic base, to> 7, particularly preferably to a pH, by adding the base from> 8.
  • the organic solvent of the water-containing pigment dispersion according to the invention is removed.
  • the solvent is removed by distillation, preferably under reduced pressure.
  • a pigment dispersion is usually obtained which, if desired, can be freed from any particles which may settle out, if desired, by sieving or decanting.
  • Another object of the present invention are the pigment dispersions obtainable by the process according to the invention.
  • the present invention also relates to the use of compound (I) for producing the pigment dispersions according to the invention.
  • the present invention further relates to compositions containing high molecular weight material, in particular high molecular weight organic material, and a dye-effective amount of the pigment dispersions according to the invention or of the compound (I).
  • the pigment dispersion or compound (I) according to the invention is preferably used in an amount of 0.001 to 75% by weight, preferably 0.01 to 50% by weight, based on the weight of the composition.
  • the present invention further relates to the use of the compositions and pigment dispersions according to the invention and of compound (I) for dyeing and pigmenting high molecular weight material, which can be organic or inorganic, and can mean plastics and / or natural substances.
  • It can be, for example, natural resins or dry oils, rubber or casein or modified natural substances such as chlorinated rubber, oil-modified alkyd resins, viscose, cellulose ethers or esters such as ethyl cellulose, cellulose acetate, propionate or propionate or butyrate, celulose acetate butyrate and in particular nitrocellulose but fully synthetic organic polymers (thermosets and thermoplastics), as can be obtained by polymerization, for example by polycondensation or polyaddition.
  • the class of polymers includes, for example, polyolefins such as polyethylene, polypropylene, polyisobutylene, further substituted polyolefins such as polymers of monomers such as vinyl chloride, vinyl acetate, styrene, acrylonitrile, acrylic acid esters, methacrylic acid esters, fluoropolymerizates such as polyfluorethylene, polytrifluorochlorethylene or tetrafluoropropylene / hexafluoropropylene / hexafluoropropylene / mixed-fluorafluorethylene and copolymers of the monomers mentioned, in particular ABS (acrylonitrile / butadiene / styrene) or EVA (ethylene / vinyl acetate).
  • polyolefins such as polyethylene, polypropylene, polyisobutylene
  • further substituted polyolefins such as polymers of monomers such as vinyl chloride, vinyl acetate, s
  • polyesters used as coating resins either saturated or similar Alkyd resins, as well as unsaturated such as maleic resins, also use linear polyesters, polyamides, polyurethanes, polycarbonates, polyphenylene oxides or silicones, silicone resins.
  • the high-molecular compounds mentioned can be present individually or in mixtures as plastic masses, melts or in the form of spinning solutions.
  • the present invention therefore preferably relates to the use of the compositions and pigment dispersions according to the invention and of compound (I) for the production of inks, for printing inks in printing processes, for flexographic printing, screen printing,
  • Packaging printing, security color printing, gravure printing or offset printing, for prepress and for textile printing, for office, home or graphic applications such as for paper goods, for ballpoint pens, felt pens, fiber pens, cardboard, wood, (wood) stains, metal, ink pads or inks for Impact-printing process (with butt printing ribbons) for the production of
  • Colorants for lacquers, for industrial or commercial use, for textile decoration and industrial marking, for roller lacquers or powder lacquers or for automotive lacquers, for high-solids (low-solvent), water-based or metallic lacquers or for pigmented formulations for aqueous paints, for the Manufacture of pigmented plastics for coatings, fibers, plates or mold carriers, for the manufacture of non-impact printing material for digital printing (digital
  • Color filters in particular for visible light in the range from 400 to 700 nm, for
  • LCD Liquid crystal displays
  • CCD Charge Combined Device
  • Cosmetics or for the production of polymeric color particles, toners, dry copy toners, liquid copy toners or electrophotographic toners are considered Cosmetics or for the production of polymeric color particles, toners, dry copy toners, liquid copy toners or electrophotographic toners.
  • the compound according to the invention is optionally mixed in the form of masterbatches with the high molecular weight materials using rolling mills, mixing or grinding apparatus.
  • the pigmented material is then per se known processes such as calendering, pressing, extrusion, painting, casting or injection molding brought into the desired final shape.
  • plasticizers to the high molecular weight organic compounds before the deformation in order to produce non-rigid moldings or to reduce their brittleness.
  • esters of phosphoric acid, phthalic acid or sebacic acid can serve as such.
  • the plasticizers can be added to the polymers before or after incorporation of the compounds obtained according to the invention. It is also possible to add fillers or other coloring constituents, such as white, colored or black pigments, to the high molecular weight, organic substances in addition to the compounds obtained according to the invention in order to achieve different colors.
  • the high molecular weight organic materials and the pigment dispersions or compound (I) obtained according to the invention are, if appropriate, dispersed or dissolved together with additives, such as fillers, other pigments, siccatives or plasticizers, in a common organic solvent or solvent mixture . You can do this by dispersing or dissolving the individual components for yourself or several together, and only then bringing all the components together.
  • the present invention therefore further relates to a process for the preparation of the compositions according to the invention by adding a dye-effective amount of the pigment dispersions or compound (I) according to the invention to high-molecular material.
  • the present invention relates to inks containing a dye-effective amount of the pigment dispersion according to the invention or of compound (I) or the composition according to the invention.
  • the inks can be produced, for example, by mixing the pigment dispersions according to the invention with polymeric dispersants.
  • the pigment dispersions are preferably mixed with the polymeric dispersant by generally known methods of mixing, such as stirring or mixing, and it is preferable to use intensive mixers such as Ultraturax.
  • the weight ratio of the pigment dispersion to the ink is expediently selected in the range from 0.001 to 75% by weight, preferably from 0.01 to 50% by weight, based on the total weight of the ink.
  • suitable polymeric dispersants are polyacrylic resins containing carboxylic acid groups, such as polymeric methacrylic or crotonic acids, in particular those obtained by polymerizing acrylic acid or acrylic acid and other acrylic monomers such as acrylic acid esters.
  • a small proportion of a water-miscible organic solvent can be added in 0.01 to 30% by weight, based on the total weight of the ink, and / or water and / or bases, so that a pH in the range of 7 to 11 is reached. It can also be advantageous to add preservatives, anti-foaming agents, surfactants, light stabilizers and pH regulators to the ink according to the invention, for example.
  • Suitable pH regulators are, for example, inorganic salts such as lithium hydroxide or carbonate, quaternary ammonium hydroxide or carbonate.
  • preservatives and antifoams are, for example, sodium dehydroacetate, 2,2-dimethyl-6-acetoxydioxane or ammonium thioglycolate.
  • Known agents which regulate the viscosity or the surface tension and are described, for example, in US Pat. No. 5,085,698 can also be used.
  • Water-miscible organic solvents are, for example, aliphatic CC 4 alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or diacetone alcohol, furthermore polyols, cellosolves and carbitols such as ethylene glycol, diethylene glycol, triethylene glycol, glycerol, propylene glycol, ethylene glycol monomethyl or monoethyl ether, propylene glycol methyl ether, dipropylene glycol ethylene glycol, ethylene glycol ether, triphylene glycol, methyl ethylene glycol, methyl ether, triphylene glycol .Triethylene glycol monomethyl or monoethyl ether, also N-methyl-2-pyrrolidone, 2-pyrrolidone, N, N'-d
  • the ink prepared as described above can still be refurbished.
  • the ink can be worked up by the customary methods for working up dispersions by separation processes such as sieving or centrifuging the coarse particles from the dispersion obtained. It has proven advantageous to centrifuge in two stages of different intensities. First at 10 minutes to 1 hour at 2000 to 4000 rpm and then at 10 minutes to 1 hour at 6000 to 10000 rpm.
  • the dispersion After centrifugation or sieving, the dispersion can be used directly as an ink for, for example, inkjet printing.
  • the present invention therefore also relates to a process for the preparation of inks by mixing high molecular weight organic material with a dye-effective amount of the pigment dispersions according to the invention or with compound (I) or the compositions according to the invention.
  • the present invention relates to a method for producing color filters containing a transparent substrate and a red, blue and green layer applied thereon in any order by the red, blue and green layer each having a correspondingly colored pigment dispersion according to the invention or a compound (I ) or an inventive composition containing pigmented high molecular weight organic material.
  • the differently colored layers preferably have such patterns that they do not overlap on at least 5% of their respective area and very particularly preferably do not overlap at all.
  • the color filters can be coated, for example, using inks, in particular printing inks, which contain the pigment dispersions according to the invention, or, for example, by mixing a pigment dispersion according to the invention with chemically, thermally or photolytically structurable high-molecular material (resist).
  • the further production can be carried out, for example, analogously to EP-A 654 711, by application to a substrate, such as an LCD, followed by photostructuring and development.
  • the pigment dispersions according to the invention which have non-aqueous solvents or dispersion media for polymers are particularly preferred for the production of color filters.
  • the invention comprises a transparent substrate, which is coated with a red, blue and green layer, each with a correspondingly colored pigment dispersion according to the invention or a compound (I) or a composition according to the invention, containing pigmented high molecular weight organic material.
  • the order of the coating is usually irrelevant.
  • the differently colored layers preferably have such patterns that they do not overlap on at least 5% of their respective area, particularly preferably do not overlap at all.
  • the present invention also includes color filters containing a transparent substrate and a red, blue and green layer, each available from one, applied thereon correspondingly colored pigment dispersion according to the invention or containing compound (I) or a composition according to the invention.
  • the present invention relates to toners containing a pigment dispersion according to the invention or a compound (I) or a composition according to the invention containing pigmented high molecular weight organic material in an amount which is effective in dyeing.
  • the present invention relates to processes for the production of toner by mixing together a high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion or compound (I) according to the invention or a composition according to the invention containing pigmented high molecular weight material.
  • toners, lacquers, inks or colored plastics are produced by processing masterbatches of toners, lacquers, inks or colored plastics in rolling mills, mixing or grinding machines.
  • the present invention relates to colorants containing a pigment dispersion according to the invention or a compound (I) or a composition according to the invention containing pigmented high molecular weight organic material in an amount which is effective in terms of dyeing.
  • the present invention relates to a process for the preparation of colorants by mixing a high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion or compound (I) according to the invention or a composition according to the invention containing pigmented high molecular weight material.
  • the present invention relates to colored plastics or polymeric color particles containing a pigment dispersion according to the invention or a compound (I) or a composition according to the invention, containing pigmented high molecular weight organic material in a dye-effective amount.
  • the present invention relates to a process for the production of colored plastics or polymeric color particles by mixing together a high molecular weight organic material and a coloring effective amount of the disperse pigment dispersion or compound (I) according to the invention or a composition according to the invention containing pigmented high molecular material.
  • the present invention relates to non-impact printing material containing a pigment dispersion according to the invention or a compound (I) or a composition according to the invention containing pigmented high molecular weight organic material in a dye-effective amount.
  • the present invention relates to a process for producing non-impact printing material by mixing a high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion or compound (I) according to the invention or a composition according to the invention containing pigmented high molecular material .
  • a dye-effective amount of the disperse pigment dispersion according to the invention or of the compound (I) or a composition according to the invention containing pigmented high-molecular material generally means 0.0001 to 99.99% by weight, preferably 0.001 to 50% by weight and particularly preferably 0.01 to 50 wt .-% based on the total weight of the material pigmented with it.
  • the process according to the invention produces very fine pigment dispersions without the high energy, time and apparatus requirements required for grinding and evaporation techniques.
  • the pigment dispersions are characterized by high stability and transparency.
  • the pigmentations achieved with the pigment dispersions or compound (I) according to the invention have high heat stability, color strengths, brilliance and transparency.
  • pigment powder compound (I) prepared according to US-3,394,123, and 4 moles of sodium chloride are mixed with 1 mole of diaethylene glycol and then kneaded in a Z-blade kneader
  • the styrene-acrylic resin has a viscosity of 11.5 sec with a dilution of 50 g of this solution with 43 g of water and 7 g of isopropanol (Ford Cup No. 4)
  • Example 5
  • 39.6 g of the filter cake from Example 2 are mixed with 350 g of a solution of 30% by weight of styrene-acrylic resin * (for example Joncryl SCX 8082 from Johnson) and 19 g of water and 5 g of isopropanol and then ground in one for 10 minutes Bead mill with zirconium oxide balls with a diameter of 1-1.6 mm. The mixture obtained is then sieved and the desired concentrate is isolated as an eluate. After 24 hours, the concentrate visually shows neither flocculation nor sedimentation.
  • styrene-acrylic resin * for example Joncryl SCX 8082 from Johnson
  • 22.5 g of a concentrate according to Example 4 are mixed with 6 g of a solution containing 30% by weight of styrene-acrylic resin * (for example Joncryl SCX 8082 from Johnson), 6 g of diethylene glycol, 0.2 g of a fluorosurfactant Diethylene glycol, 0.1 g butyl sulfoxide and 0.1 ml tributyl phosphate and 40 g water.
  • This mixture is then mixed for 5 minutes in an Ultraturrax and then centrifuged for 30 minutes at 3000 rpm and then for 30 minutes at 8000 rpm.
  • the supernatant solution is poured off and filled as ink into a commercially available ink jet printer. A test print with this ink is characterized by high color strength.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Paints Or Removers (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

L'invention concerne des dispersions pigmentaires contenant (a) un polymère, (b) un composé de la formule (I) et (c) un solvant ne contenant pas d'eau ou (d) un solvant contenant de l'eau. L'invention concerne en outre un procédé permettant de le préparer, ainsi que l'utilisation de (I) et des dispersions pigmentaires obtenues selon l'invention.
EP98936394A 1997-06-30 1998-06-29 Dispersions pigmentaires contenant le pigment c.i. rouge 222 Withdrawn EP0993489A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH157397 1997-06-30
CH157397 1997-06-30
CH289697 1997-12-16
CH289697 1997-12-16
PCT/EP1998/003949 WO1999001512A1 (fr) 1997-06-30 1998-06-29 Dispersions pigmentaires contenant le pigment c.i. rouge 222

Publications (1)

Publication Number Publication Date
EP0993489A1 true EP0993489A1 (fr) 2000-04-19

Family

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Family Applications (2)

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EP98938669A Expired - Lifetime EP0993490B1 (fr) 1997-06-30 1998-06-29 Procede de preparation de dispersions pigmentaires fines
EP98936394A Withdrawn EP0993489A1 (fr) 1997-06-30 1998-06-29 Dispersions pigmentaires contenant le pigment c.i. rouge 222

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP98938669A Expired - Lifetime EP0993490B1 (fr) 1997-06-30 1998-06-29 Procede de preparation de dispersions pigmentaires fines

Country Status (8)

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US (3) US6071989A (fr)
EP (2) EP0993490B1 (fr)
JP (2) JP2002508802A (fr)
KR (1) KR20010014330A (fr)
CN (1) CN1261908A (fr)
AU (2) AU8541098A (fr)
DE (1) DE59807324D1 (fr)
WO (2) WO1999001512A1 (fr)

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Also Published As

Publication number Publication date
US6001168A (en) 1999-12-14
DE59807324D1 (de) 2003-04-03
KR20010014330A (ko) 2001-02-26
US6071989A (en) 2000-06-06
EP0993490A1 (fr) 2000-04-19
JP2002508802A (ja) 2002-03-19
AU8730198A (en) 1999-01-25
US6211347B1 (en) 2001-04-03
WO1999001511A1 (fr) 1999-01-14
CN1261908A (zh) 2000-08-02
AU8541098A (en) 1999-01-25
JP2002514263A (ja) 2002-05-14
EP0993490B1 (fr) 2003-02-26
WO1999001512A1 (fr) 1999-01-14

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