EP2121851A1 - Composition d'epsilon-phtalocyanine de cuivre (pigment bleu 15:6) en fine particule destinée à être utilisée comme pigment - Google Patents

Composition d'epsilon-phtalocyanine de cuivre (pigment bleu 15:6) en fine particule destinée à être utilisée comme pigment

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Publication number
EP2121851A1
EP2121851A1 EP07856447A EP07856447A EP2121851A1 EP 2121851 A1 EP2121851 A1 EP 2121851A1 EP 07856447 A EP07856447 A EP 07856447A EP 07856447 A EP07856447 A EP 07856447A EP 2121851 A1 EP2121851 A1 EP 2121851A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
additive
pigment
alkoxy
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Withdrawn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
EP07856447A
Other languages
German (de)
English (en)
Inventor
Thomas Metz
Gerald Mehltretter
Klaus Brychcy
Carsten Plüg
Wolfgang Schäfer
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 Finance BVI Ltd
Original Assignee
Clariant Finance BVI Ltd
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 Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2121851A1 publication Critical patent/EP2121851A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0025—Crystal modifications; Special X-ray patterns
    • C09B67/0026—Crystal modifications; Special X-ray patterns of phthalocyanine pigments
    • 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
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0002—Grinding; Milling with solid grinding or milling assistants
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C09B67/0008—Coated particulate pigments or dyes with organic coatings
    • 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
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0016—Influencing the physical properties by treatment with a liquid, e.g. solvents of phthalocyanines
    • 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
    • C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
    • 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
    • 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
    • C08K5/0091—Complexes with metal-heteroatom-bonds

Definitions

  • Finely divided epsilon-copper phthalocyanine composition (Pigment Blue 15: 6) for use as a pigment
  • the present invention relates to a pigment composition of finely divided copper phthalocyanine in the epsilon modification (Pigment Blue 15: 6, Cl 74160), and a process for the phase transformation of alpha or gamma phase in the epsilon phase.
  • the epsilon modification represents the crystal phase with the most reddish blue. Furthermore, it has a high color strength and shows a particularly pure hue. These properties make Cl. Pigment Blue 15: 6 is of particular interest for special applications, for example in coatings, printing or plastics, as well as in the field of color filters for use in optical displays or as pigmented photoresists.
  • the stability of the epsilon phase lies between the alpha and the beta phase. This complicates the phase-pure production of the epsilon modification.
  • the production of the epsilon modification can be carried out by various processes: during the crude blue synthesis (US Pat. Nos. 3,051,721, 4,135,944), by treatment of copper phthalocyanine in organic solvents and their mixtures with water (DE-2 210 072, EP-1 580 239 ) or by salt kneading (EP-1 130 065). All methods have in common that the compliance with special production parameters and the addition of additives, the epsilon modification is stabilized, so that a conversion is prevented in the thermodynamically more stable beta-modification.
  • the object of the present invention was to find an additive which allows the preparation of a copper phthalocyanine composition with as pure a phase as possible epsilon modification and reddish hue as possible. Furthermore, the desired additives should act in different stages of the process phthalocyanine synthesis phase stabilizing.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently hydrogen; C 1 -C 22 alkyl or C 2 -C 2 2 alkenyl, the carbon chain of each of which is replaced by one or more of Groupings -O-, -S-, -NR 9 -, -CO- or SO 2 - may be interrupted and / or monosubstituted or polysubstituted by hydroxyl, halogen, aryl, heteroaryl, Ci-C 4 alkoxy and / or acetyl can be;
  • C 3 -C 8 -cycloalkyl whose carbon skeleton may be interrupted by one or more groups -O-, -S-, -NR 10 -, -CO- or SO 2 - and / or mono- or polysubstituted by hydroxyl, halogen, Aryl, heteroaryl, Ci-C 4 alkoxy and / or acetyl may be substituted; Dehydroabietyl or aryl or heteroaryl, wherein
  • R 9 and R 10 independently of one another are hydrogen or C 1 -C 22 -alkyl, or where R 3 , R 4 , R 5 , R 6 are a polyoxyalkylene chain which is optionally terminally alkylated.
  • Aryl is preferably C 6 -C 0 aryl, in particular phenyl or naphthyl.
  • Heteroaryl means preferably a five- or six-membered heteroaromatic ring having 1, 2, 3 or 4 heteroatoms from the group N, O and S, which is optionally benzoannelated.
  • R 1 , R 2 , R 4 and R 6 are preferably hydrogen.
  • R 3 and R 5 are preferably (C 2 -C 4 -alkylene) -O- (C 1 -C 6 -alkyl).
  • a preferred additive for the purposes of the present invention is a compound of the general formula (2)
  • R 7 and R 8 are independently hydrogen; C 1 -C 19 alkyl or C 2 -C 9 alkenyl whose carbon chain may be interrupted by one or more of the groupings -O-, -S-, -NR 9 -, -CO- or SO 2 - and / or a - or may be substituted several times by hydroxy, halogen, C 1 -C 4 alkoxy and / or acetyl, or a radical of the formula - (AO) n -Z, where A is ethylene or propylene, Z is hydrogen or Ci-Ci 6 - Alkyl, and n is a number from 1 to 200, preferably from 10 to 100; C 3 -C 8 -cycloalkyl whose carbon skeleton may be interrupted by one or more groups -O-, -S-, -NR 10 -, -CO- or SO 2 - and / or mono- or polysubstituted by hydroxyl, halogen, Ci-C
  • the additive of the formula (3) is particularly preferred.
  • Additives of the formulas (1), (2) and (3) can be prepared in a manner known per se by reacting naphthyl diisocyanate with the corresponding amines.
  • the invention relates to a process for the preparation of copper phthalocyanine in the epsilon modification, characterized in that copper phthalocyanine of the alpha modification, the gamma modification, or a mixture of alpha and gamma modification, in the presence of 1 to 50 wt .-%, preferably 5 to 15 wt .-%, of crystalline epsilon modification O
  • Wet milling is understood to mean customary milling processes in bead mills or stirred ball mills.
  • Suitable grinding media are all those known in the literature, for example spheres and, as materials, steel, porcelain, steatite, oxides, such as alumina or optionally stabilized zirconium oxide, mixed oxides, such as zirconium mixed oxide, or glass, such as quartz glass.
  • the grinding can take place at temperatures up to 150 0 C, usually temperatures below 100 0 C are applied.
  • the residence time depends on the rate of phase transformation.
  • a particularly preferred form of wet milling is salt kneading with a crystalline inorganic salt in the presence of an organic solvent.
  • Suitable crystalline inorganic salts are, for example, aluminum sulfate, sodium sulfate, calcium chloride, potassium chloride or sodium chloride, preferably sodium sulfate, sodium chloride and potassium chloride.
  • Suitable organic solvents are, for example, ketones, esters, amides, sulphones, sulphoxides, nitro compounds, mono-, bis- or tris-hydroxy-C 2 -C 12 -alkanes which may be substituted by C 1 -C 6 -alkyl and one or more hydroxyl groups, into consideration.
  • water-miscible high-boiling organic solvents based on monomeric, oligomeric and polymeric C 2 -C 3 -alkylene glycols, such as diethylene glycol, diethylene glycol monomethyl and ethyl ether, triethylene glycol, triethylene glycol monomethyl and ethyl ether, dipropylene glycol, dipropylene glycol monomethyl and ethyl ether, propylene glycol monomethyl and ethyl ether and liquid polyethylene and polypropylene glycols, N-methylpyrrolidone and also triacetin, dimethylformamide, dimethylacetamide, ethyl-methyl- ketone, cyclohexanone, diacetone alcohol, butyl acetate, nitromethane, dimethylsulfoxide and sulfolane.
  • monomeric, oligomeric and polymeric C 2 -C 3 -alkylene glycols such as diethylene glycol, diethylene glycol monomethyl
  • the weight ratio between the inorganic salt and the copper phthalocyanine is preferably (2 to 8) to 1, especially (5 to 6) to 1.
  • the weight ratio between the organic solvent and the inorganic salt is preferably (1 ml: 6 g) to (3 ml: 7 g).
  • the weight ratio between the organic solvent and the sum of inorganic salt and copper phthalocyanine is preferably (1 ml: 2.5 g) to (1 ml: 7.5 g).
  • the temperature during the kneading can be between 40 and 140 ° C., preferably between 60 and 120 ° C.
  • the kneading time is expediently 4 hours to 32 hours, preferably 8 hours to 20 hours.
  • the inorganic salt and the organic solvent are expediently removed by washing with water, and the resulting pigment composition is dried by conventional methods.
  • the wet milling in particular salt kneading, is followed by a solvent finish.
  • the solvent treatment can be carried out in an organic solvent, preferably from the group of alcohols having 1 to 10 C atoms, such as, for example, methanol, ethanol, n-propanol, isopropanol, butanols, such as n-butanol, isobutanol, tert-butanol , Pentanols such as n-pentanol, 2-methyl-2-butanol, hexanols, such as
  • glycols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, sorbitol or glycerol;
  • Polyglycols such as polyethylene or polypropylene glycols;
  • Ethers such as methyl isobutyl ether, tetrahydrofuran, dimethoxyethane or dioxane;
  • Glycol ethers such as monoalkyl ethers of ethylene or propylene glycol or diethylene glycol monoalkyl ethers, where alkyl may be methyl, ethyl, propyl, and butyl, for example butylglycols or methoxybut
  • Preferred solvents are C 1 -C 6 -AlkOhOIe, in particular methanol, ethanol, n- and isopropanol, isobutanol, n- and tert-butanol and tert-amyl alcohol; C 3 -C 6 -ketones, in particular acetone, methyl ethyl ketone or diethyl ketone; Tetrahydrofuran, dioxane, ethylene glycol, diethylene glycol or ethylene glycol C 3 -C 5 - alkyl, in particular 2-methoxyethanol, 2-ethoxyethanol, butyl glycol, toluene, xylene, ethylbenzene, chlorobenzene, o-dichlorobenzene, nitrobenzene, cyclohexane, diacetone alcohol or methylcyclohexane.
  • C 1 -C 6 -AlkOhOIe in particular methanol,
  • Particularly preferred solvent is tetrahydrofuran.
  • the solvent may also contain water, acids or alkalis. Particularly suitable is tetrahydrofuran and 0.1 to 20 wt .-% aqueous sulfuric acid in the ratio 1: 1 to 1: 3.
  • the solvent treatment is 50 to 120 0 C, carried out advantageously for 1 to 8 h and at a temperature between 30 and 200 ° C, preferably.
  • the additive according to the invention may be added to the copper phthalocyanine in an amount of from 0.5 to 15% by weight, preferably from 2 to 5% by weight, before and / or during the wet milling or before and / or during the solvent treatment in one or more portions. be added. It has been found that with larger amounts (over 15% by weight) of the additive, the phase transformation from the alpha to the epsilon phase is greatly slowed down, so that the process is no longer economical.
  • the additive remains in the process of the invention for the most part on the Pigment Blue 15: 6 surface.
  • the alpha-copper phthalocyanine used can be prepared by known processes, for example starting from a swelling or dissolution process in 60 to 100% strength by weight sulfuric acid.
  • Copper phthalocyanine as well as mixtures of alpha / gamma phase are also possible.
  • the addition of the epsilon seed crystals to the alpha and / or gamma phase may be done with or without prior milling, but preferably the mixtures are made by vibrating, rolling, ball, planetary or bead milling.
  • the naphthyl additives according to the invention exhibit their phase-stabilizing effect both in a simple solvent treatment and in a wet-milling process, for example in salt-kneading.
  • the advantage is that the same additive both for the production of a finely divided transparent epsilon-Kupferphthalocyanins (particle size 20 to 90 nm, prepared by wet milling) and for the production of a opaque epsilon copper phthalocyanine (particle size 90 to 300 nm, prepared by solvent treatment without wet milling) is suitable.
  • the pigment composition prepared according to the present invention has a primary particle size of preferably 20 to 300 nm and a length / breadth ratio of the primary grain of (1, 0 to 6.0) to 1, preferably (1, 0 to 3.0) to 1.
  • the specific surface area (BET) is preferably 50 to 100 m 2 / g.
  • the invention also provides a pigment composition of Cl. Pigment Blue 15: 6, containing 0.5 to 15 wt .-%, preferably 2 to 5 wt .-%, of an additive of the formula (1), based on the weight of the pigment.
  • the pigment composition according to the invention may contain, in addition to the copper phthalocyanine pigment and the additive of the formula (1), further customary auxiliaries or additives, for example surfactants, nonpigmentary dispersants, fillers, setting agents, resins, waxes, defoamers, anti-dust agents, extenders, antistatic agents, preservatives, Drying delay agents, rheology control additives, wetting agents, antioxidants, UV absorbers and light stabilizers, preferably in an amount of 0.1 to 25 wt .-%, in particular 0.5 to 15 wt .-%, based on the total weight of the pigment -Composition.
  • auxiliaries or additives for example surfactants, nonpigmentary dispersants, fillers, setting agents, resins, waxes, defoamers, anti-dust agents, extenders, antistatic agents, preservatives, Drying delay agents, rheology control additives, wetting agents, antioxidants, UV absorbers and light stabilizers,
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic or amphoteric substances or mixtures of these agents.
  • Anionic substances for example, fatty acid taurides, fatty acid N-methyltaurides, fatty acid isethionates, alkylphenyl, such as dodecylbenzenesulfonic acid, alkylnaphthalenesulfonates, Alkylphenolpolyglykolether- come sulfate, fatty alcohol polyglycol ether, fatty acid amide polyglycol ether sulfates, ethersulfosuccinate alkyl sulfosuccinates, alkenylsuccinic, fatty alcohol polyglycol, alkane sulfonates, fatty acid glutamates, alkyl sulfosuccinates, fatty acid sarcosides; Fatty acids, for example palmitic, stearic and oleic acids; the salts of these anionic substances and soaps, for example alkali metal salts of fatty acids, naphthenic acids and resin acids, for example
  • cation-active substances are, for example, quaternary ammonium salts, Fettaminoxalkylate, polyoxyalkyleneamines, alkoxylated polyamines, Fettaminpolyglykolether, primary, secondary or tertiary amines, for example alkyl, cycloalkyl or cyclized alkylamines, especially fatty amines derived from fatty amines or fatty alcohols di- and polyamines and their alkoxylates of Fatty acid derived imidazolines, polyaminoamido or polyamine compounds or resins having an amine index between 100 and 800 mg KOH per g of the polyaminoamido or polyamino compound, and salts of these cationic substances, such as acetates or chlorides into consideration.
  • nonionic and amphoteric substances are fatty amine carboxyglycinates, amine oxides, fatty alcohol polyglycol ethers,
  • Fatty acid polyglycol esters such as fatty acid amide N-propyl betaines, phosphoric esters of aliphatic and aromatic alcohols, fatty alcohols or fatty alcohol polyglycol ethers, fatty acid amide ethoxylates, fatty alcohol alkylene oxide adducts and alkylphenol polyglycol ethers.
  • nonpigmentary dispersants substances which are not structurally derived from organic pigments. They are used as dispersants either already in the production of pigments, but often also during the incorporation of the pigments into the application media to be dyed, for example in the production of paints or printing inks
  • pigments in the appropriate binders may be polymeric substances, for example polyolefins, polyesters, polyethers, polyamides, polyimines, polyacrylates, polyisocyanates, block copolymers from them, copolymers of the corresponding monomers or polymers of one class modified with a few monomers of a different class.
  • These polymeric substances carry polar anchor groups such as hydroxy, amino, imino and ammonium groups, carboxylic acid and carboxylate groups, sulfonic acid and sulfonate groups or phosphonic acid and
  • Nonpigmentary dispersants may also be chemically functional group modified aromatic non-organic pigment derived substances.
  • Nonpigmentary dispersants are known in the art and some are available commercially (for example, Solsperse ®, Avecia; Disperbyk ®, Byk-Chemie, Efka ®, Efka). In the following, a few types are to be mentioned, but in principle any other substances described can be used, for example condensation products of isocyanates and alcohols, diols or polyols, aminoalcohols or di- or polyamines, polymers
  • Hydroxycarboxylic acids copolymers of olefin monomers or vinyl monomers and ethylenically unsaturated carboxylic acids and esters, urethane-containing polymers of ethylenically unsaturated monomers, urethane-modified polyesters, condensation products based on cyanuric halides, nitroxyl-containing polymers, polyester amides, modified
  • Polyamides modified acrylic polymers, combicant-type dispersants of polyesters and acrylic polymers, phosphoric acid esters, triazine-derived polymers, modified polyethers or dispersants derived from aromatic non-pigmentary substances. These basic structures are often further modified, for example by chemical reaction with other functional groups bearing substances or by salt formation.
  • Anionic groups of the nonpigmentary dispersants, surfactants or resins used as auxiliaries can also be laked, for example by Ca, Mg, Ba, Sr, Mn or Al ions or by quaternary ammonium ions.
  • fillers or extenders are a variety of substances according to DIN 55943 and DIN EN 971-1, for example the various types of talc, kaolin, mica, dolomite, lime, barium sulfate or titanium dioxide. In this case, the addition has proven especially before the pulverization of the dried pigment preparation.
  • the pigment composition according to the invention can be used for pigmenting high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, paints, 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 of the present invention are, for example, cellulose compounds such as cellulose ethers and esters such as ethylcellulose, nitrocellulose, cellulose acetates or cellulose butyrates, natural binders such as 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, phenolic resins and phenolic resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl acetates or polyvinyl ethers, polycarbonates, Polyolefins, such as polystyrene, polyvinyl chloride, polyethylene
  • Synthetic resins polymers, acrylates
  • waxes aldehyde and ketone resins
  • rubber rubber and its derivatives and latices
  • casein silicones and silicone resins
  • the present invention therefore also relates to a high molecular weight organic material containing a dyeing effective amount of a pigment composition according to the invention.
  • the pigment composition according to the invention is usually used in an amount of from 0.01 to 30% by weight, preferably from 0.1 to 15% by weight.
  • the pigment compositions according to the invention are also suitable as
  • Colorants in electrophotographic toners and developers such as one- or two-component powder toners (also called one- or two-component developer), magnetic toner, liquid toner, polymerization toner and special toner.
  • 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 used for surface coating of articles of, for example, metal, wood, plastic, glass, ceramic, concrete, textile, paper or rubber come.
  • the pigment compositions according to the invention are suitable as colorants in aqueous and nonaqueous based ink-jet inks and also in inks which operate according to the hot-melt method.
  • Ink-jet inks generally contain a total of 0.5 to 15 wt .-%, preferably 1, 5 to 8 wt .-%, (calculated dry) of one or more of the pigment compositions of the invention.
  • Microemulsion inks are based on organic solvents, water and optionally an additional hydrotropic substance (interface mediator).
  • Microemulsion inks generally contain 0.5 to 15 wt .-%, preferably 1.5 to 8 wt .-%, one or more of the pigment compositions of the invention, 5 to 99 wt .-% water and 0.5 to 94.5 Wt .-% organic solvent and / or hydrotrope 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 usually based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range is between about 60 ° C and about 140 0 C.
  • hot-melt ink-jet inks consist essentially 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.
  • 0 to 20 wt .-% of an additional polymer (as a "dye remover"), 0 to 5 wt .-% dispersing aid, 0 to 20 wt .-% viscosity modifier, 0 to 20 wt .-% plasticizer, 0 to 10 wt % Of tackiness additive, 0 to 10% by weight of transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight of antioxidant.
  • an additional polymer as a "dye remover”
  • dispersing aid 0 to 20 wt .-% viscosity modifier
  • plasticizer 0 to 20 wt .-% plasticizer
  • 0 to 10 wt % Of tackiness additive 0 to 10% by weight of transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight of antioxidant.
  • the pigment compositions according to the invention are also colorants for color filters, both for additive and for the subtractive color generation, such as in electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays , which in turn may be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, as well as colorants for electronic inks ("e-inks”) or "electronic paper” (“ e-paper ").
  • electro-optical systems such as television screens, LCD (liquid crystal displays), charge coupled devices, plasma displays or electroluminescent displays , which in turn may be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, as well as colorants for electronic inks ("e-inks”) or "electronic paper” (“ e-paper ").
  • a stable paste or a pigmented photoresist also has a high pigment purity
  • the pigmented color filters can also be applied by inkjet printing or other suitable printing methods.
  • the reddish blue shades of the pigment compositions according to the invention are particularly well suited for the color filter red-green-blue color set (R 1 G 1 B). These three colors are present as separate color dots side by side, and result from backlit a full color image.
  • Typical colorants for the red color point are pyrrolopyrrole, quinacridone and azo pigments, e.g. P.R. 254, P.R. 209, P.R.175 and P.O. 38, single or mixed.
  • the pigment composition according to the invention has a brilliant hue and can achieve high transparency in full tone.
  • phase purity of the pigments produced in the epsilon phase was detected by means of IR spectroscopy and X-ray powder diffractograms.
  • Example 1 Solvent treatment in the presence of the additive of the formula (3)
  • Example 3 Solvent treatment in the presence of 1 g of the additive of the formula
  • Example 4 Solvent treatment in the presence of 1 g of the additive of the formula
  • Example 5 Solvent treatment in the presence of 0.25 g of the additive of
  • Example 6 Salt kneading in the presence of the additive of the formula (3)
  • a 1 l laboratory kneader (Werner & Pfleiderer) was treated with 67.5 g of alpha copper phthalocyanine, 7.5 g of epsilon copper phthalocyanine as seeds, 3 g of additive of the formula (3), 450 g of NaCl and 120 ml of diethylene glycol.
  • the kneading time was 16 h and the kneading temperature about 95 ° C.
  • the kneaded mass was transferred to a 6 l flask and stirred with 4000 ml of dilute hydrochloric acid (5 wt .-% strength) for 2 h at room temperature. After this solvent treatment, the suspension was filtered off, the presscake washed with water at 50 0 C, dried in a convection oven for 16 h at 80 0 C and pulverized with an IKA mill. 76 g of a Pigment Blue 15: 6 composition were obtained. Physical data and coloristic test results:

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  • Life Sciences & Earth Sciences (AREA)
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Abstract

L'invention concerne une composition de pigment constituée de C.I. Pigment Blue 15:6 et qui contient par rapport au poids du pigment de 0,5 à 15 % en poids d'un additif de formule (1) dans laquelle R1, R2, R3, R4, R5 et R6 représentent indépendamment l'un de l'autre l'hydrogène, un alkyle en C1 à C22 ou un alcényle en C2 à C22 dont la chaîne d'atomes de carbone peut être interrompue à chaque fois par un ou plusieurs groupes -O-, -S-, -NR9-, -CO- ou SO2- et/ou peut être substituée une ou plusieurs fois avec un hydroxyle, un halogène, un aryle, un hétéroaryle, un alcoxy en C1 à C4 et/ou un acétyle; un cycloalkyle en C3 à C8 dont le squelette d'atomes de carbone peut être interrompu par un ou plusieurs groupes -O-, -S-, -NR10-, -CO- ou SO2- et/ou être substitué une ou plusieurs fois avec un groupe hydroxyle, halogène, aryle, hétéroaryle, un alcoxy en C1 à C4 et/ou un acétyle, un deshydroabiétyle, un aryle ou un hétéroaryle, R9 et R10 représentant indépendamment l'un de l'autre l'hydrogène ou un groupe alkyle en C1 à C22. La composition de pigment selon l'invention est préparée en utilisant un procédé de broyage en conditions humides et en particulier un pétrissage de sel.
EP07856447A 2007-01-12 2007-12-07 Composition d'epsilon-phtalocyanine de cuivre (pigment bleu 15:6) en fine particule destinée à être utilisée comme pigment Withdrawn EP2121851A1 (fr)

Applications Claiming Priority (2)

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DE102007001851A DE102007001851A1 (de) 2007-01-12 2007-01-12 Feinteilige Epsilon-Kupferphthalocyanin-Komposition (Pigment Blau 15:6) zur Verwendung als Pigment
PCT/EP2007/010642 WO2008083799A1 (fr) 2007-01-12 2007-12-07 Composition d'epsilon-phtalocyanine de cuivre (pigment bleu 15:6) en fine particule destinée à être utilisée comme pigment

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EP2121851A1 true EP2121851A1 (fr) 2009-11-25

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CN (1) CN101563426A (fr)
DE (1) DE102007001851A1 (fr)
WO (1) WO2008083799A1 (fr)

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EP2115073B1 (fr) * 2007-02-07 2014-03-12 Basf Se Composition de pigment de phtalocyanine bleue et sa préparation
DE102007033191A1 (de) 2007-07-17 2009-01-22 Clariant International Ltd. Feinteilige epsilon-Kupferphthalocyanin-Pigmentzubereitung
JP5566399B2 (ja) * 2008-12-23 2014-08-06 ソルヴェイ（ソシエテ アノニム） イプシロン結晶学的形態を示す銅フタロシアニン粒子の効率的な製造方法
JP2011116876A (ja) * 2009-12-04 2011-06-16 Seiko Epson Corp インクセット、記録装置、および記録方法
CN103403101A (zh) * 2010-12-22 2013-11-20 索尔维公司 制备基于酞菁铜(CuPc)颗粒的产物的方法
JP5664834B1 (ja) * 2013-07-31 2015-02-04 Dic株式会社 フタロシアニン顔料組成物の製造方法
JP7203573B2 (ja) * 2017-11-16 2023-01-13 住友化学株式会社 青色硬化性樹脂組成物、青色カラーフィルタ及びそれを含む表示装置
CN112111060B (zh) * 2020-09-28 2022-07-05 潍坊光华精细化工有限公司 一种多孔有机骨架材料及其制备方法和在选择性分离高铼酸根中的应用

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US3051721A (en) 1959-01-13 1962-08-28 American Cyanamid Co Pigmentary copper phthalocyanine in the "r" form and its preparation
BE795946A (fr) 1972-03-02 1973-08-27 Basf Ag Procede de preparation de pigments de phtalocyanine cuivrique (variete epsilon)
DE2742066A1 (de) 1976-09-21 1978-03-23 Ciba Geigy Ag Kupferphthalocyanin-pigmentzusammensetzungen und verfahren zu deren herstellung
DE2906111C3 (de) * 1979-02-17 1984-02-09 Basf Ag, 6700 Ludwigshafen Pigmentzubereitungen für Druck- und Lackfarben
DE3211165A1 (de) * 1982-03-26 1983-09-29 Basf Ag, 6700 Ludwigshafen Pigmentzubereitungen und deren verwendung zum pigmentieren von tiefdruck- und lackfarben
JPS61266471A (ja) * 1985-05-21 1986-11-26 Dainichi Color & Chem Mfg Co Ltd 銅フタロシアニン青色顔料の製造方法
JPH086271A (ja) * 1994-06-17 1996-01-12 Mitsubishi Chem Corp 電子写真感光体及びその製造方法
EP1130065B1 (fr) 2000-02-04 2006-03-08 Dainichiseika Color & Chemicals Mfg. Co. Ltd. Compositions pigmentaires, leurs procédés de préparations, colorants et articles colorés
US7211664B2 (en) 2004-03-26 2007-05-01 Toyo Ink Mfg. Co., Ltd. Process for the production of epsilon crystal form copper phthalocyanine

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DE102007001851A1 (de) 2008-07-17
CN101563426A (zh) 2009-10-21
WO2008083799A1 (fr) 2008-07-17
KR20090122183A (ko) 2009-11-26
US20100086868A1 (en) 2010-04-08
JP2010515789A (ja) 2010-05-13

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