EP2167586A2 - Préparations pigmentaires à base de pigment bleu c.i. 15:6 - Google Patents

Préparations pigmentaires à base de pigment bleu c.i. 15:6

Info

Publication number
EP2167586A2
EP2167586A2 EP08759258A EP08759258A EP2167586A2 EP 2167586 A2 EP2167586 A2 EP 2167586A2 EP 08759258 A EP08759258 A EP 08759258A EP 08759258 A EP08759258 A EP 08759258A EP 2167586 A2 EP2167586 A2 EP 2167586A2
Authority
EP
European Patent Office
Prior art keywords
pigment
parts
alkyl
radicals
formula
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Withdrawn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
EP08759258A
Other languages
German (de)
English (en)
Inventor
Jens Reichwagen
Carsten Plüg
Thomas Metz
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
Priority claimed from DE102007033192A external-priority patent/DE102007033192A1/de
Priority claimed from DE102008009194A external-priority patent/DE102008009194A1/de
Application filed by Clariant Finance BVI Ltd filed Critical Clariant Finance BVI Ltd
Publication of EP2167586A2 publication Critical patent/EP2167586A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • 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
    • 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
    • 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
    • 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
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/19—Quaternary ammonium compounds
    • 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
    • C09B67/002—Influencing the physical properties by treatment with an amine
    • 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
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0035—Mixtures of phthalocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
    • C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
    • 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 novel finely divided pigment preparations with Cl. Pigment Blue 15: 6 as a base pigment and certain pigment dispersants and their use in particular for color filters.
  • Copper phthalocyanine pigments for color filter applications often have very high viscosity and poor viscosity stability. Also, the finely divided pigments are highly prone to agglomerate and aggregate, which is particularly detrimental to transparency, color strength and especially the contrast ratio of the color filters produced with these pigments.
  • the contrast ratio KV
  • the light intensity is determined after irradiating a pigmented lacquer layer on a transparent substrate, in which the substrate is located between two polarizers.
  • the contrast ratio indicates the ratio of the light intensities in parallel and perpendicular polarizers.
  • EP-A 0 638 615 describes the salt kneading of crude copper phthalocyanines in the presence of copper phthalocyanine sulphonic acid ammonium salts for use in printing inks.
  • a disadvantage of this method is the conversion of un-stabilized crude copper phthalocyanines into the undesirable beta phase in the salt kneading process.
  • JP 2005-234009 describes pigment preparations which, besides epsilon-copper phthalocyanines, contain sulfonamides, phthalimidomethyl derivatives and sulfonic acids of copper phthalocyanines.
  • sulfonamides e.g., phthalimidomethyl derivatives
  • sulfonic acids copper phthalocyanines.
  • JP 2005-234009 describes pigment preparations which, besides epsilon-copper phthalocyanines, contain sulfonamides, phthalimidomethyl derivatives and sulfonic acids of copper phthalocyanines.
  • JP 2005-234009 describes pigment preparations which, besides epsilon-copper phthalocyanines, contain sulfonamides, phthalimidomethyl derivatives and sulfonic acids of copper phthalocyanines.
  • the synergists generally have a more greenish hue than the epsilon copper phthalocyan
  • WO 02/48268 and WO 02/48269 describe pigment preparations of organic pigments and sulfonic acid-containing pigment dispersants, which are laked with Ca ions and / or with quaternary ammonium ions. However, the preparations described do not meet the necessary high standards of contrast ratio and brilliance.
  • the object was pigment preparations with Cl. Pigment Blue 15: 6 as a base pigment to provide a pure color, high brilliance, low viscosity and high contrast ratios in color filter applications.
  • the invention relates to pigment preparations containing Cl. Pigment Blue 15: 6 with an average particle size d 5 o of 10 to 100 nm, and at least one pigment dispersant of the formula (II)
  • CPC is a residue of a copper phthalocyanine
  • n is a number from 0.1 to 4, preferably 0.2 to 2
  • m is a number from 0.1 to 4, preferably 0.2 to 2
  • R 1 , R 2 , R 3 , R 4 independently of one another are each hydrogen, or a radical from the group C 1 -C 20 -alkyl, C 2 -C 2 o-alkenyl, C 5 -C 2 o-cycloalkyl, C 5 -C 2 o-cycloalkenyl, Ci-C- 4- alkyl-phenyl, wherein the aforementioned radicals are optionally branched and optionally substituted by sulfo, carboxy, hydroxy and halogen, with the proviso that one, two or three of the radicals R 1 to R 4 are hydrogen.
  • R is a radical from the group CrC 2O- alkyl, C 2 -C 2 o-alkenyl,
  • M is a number from 0.1 to 4, preferably 0.2 to 2
  • Kat is a cation from the group H + , Li + , Na + and K +
  • n is a number from 0.1 to 4, preferably 0.2 to 2
  • o is a number from 0 to 3.9, preferably from 0 to 1.8.
  • the radicals R 1, R 2, R 3 and R 4 have the preferred meaning of C 6 -C 2O -alkyl, C 6 -C 2 o-alkenyl, and benzyl. with the proviso that one, two or three, in particular three, of the radicals R 1 to R 4 are hydrogen.
  • ammonium radicals NR1 R2R3R4 + are primary ammonium radicals, such as n-hexyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl , Nonadecyl, eicosyl ammonium, their monounsaturated radicals, benzyl, 2-phenylethyl ammonium; secondary ammonium radicals, such as dibutyl, dihexyl,
  • Dioctyl didecyl, 2-ethyl-hexyl, dioleyl, distearyl, dibenzyl ammonium; tertiary ammonium radicals such as dimethyloctyl, dimethyldecyl, dimethyllauryl, dimethylstearyl, trioctyl, tribenzyl, bis (2-hydroxyethyl) dodecylammonium.
  • the weight ratio of Cl. Pigment Blue 15: 6 to Pigmentdispergator of formula (II) preferably between (97 to 3) and (70 to 30), more preferably between (95 to 5) and (80 to 20).
  • the pigment preparations of the invention comprise the base pigment having a mean particle size d 5 o of 10 to 100 nm, preferably 20 to 50 nm.
  • the particle size distribution of Cl. Pigment Blue 15: 6 is preferably approximated to a Gaussian distribution.
  • the ratio of dgs / dso is preferably less than 4.0: 1, more preferably less than 3.0: 1.
  • the primary particles of the base pigment should have a length to width ratio of preferably less than 3.0: 1, more preferably less than 2.0: 1.
  • the pigment preparation according to the invention can furthermore contain 0.5 to 15% by weight, preferably 1 to 10% by weight, in particular 2 to 5% by weight, of an additive of the formula (3), in each case based on the weight of Cl.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are independently hydrogen; C 1 -C 22 alkyl or C 2 -C 22 alkenyl, whose carbon chain can be interrupted by one or more groups -O-, -S-, -NR 9 -, -CO- or SO 2 - and / or mono- or polysubstituted Hydroxy, halogen, aryl, heteroaryl, C 1 -C 4 alkoxy and / or acetyl;
  • 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, C 1 -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 13 , R 14 , R 15 and R 16 are a polyoxyalkylene chain which is optionally terminally alkylated.
  • Aryl is preferably C ⁇ -Cio-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 11 , R 12 , R 14 and R 16 are preferably hydrogen.
  • R 13 and R 15 are preferably (C 2 -C 4 -alkylene) -O- (C 1 -C 16 -alkyl).
  • a preferred additive for the purposes of the present invention is a compound of the general formula (4)
  • R 17 and R 18 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 mono- or polysubstituted 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 C 1 -C 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, C r C 4 alkoxy and / or acetyl may be substituted; where R 9 and R 10 independently of one another are hydrogen or C 1 -C 22 -alkyl.
  • the additive of the formula (5) is particularly preferred.
  • Additives of the formulas (3), (4) and (5) can be prepared in a manner known per se by reacting naphthyl diisocyanate with the corresponding amines.
  • the pigment preparations according to the invention may contain, in addition to the phthalocyanine pigment and the pigment dispersant, other customary auxiliaries or additives, such as, for example, surfactants, dispersants, fillers, setting agents, resins, waxes, defoamers, antidusting agents, extenders, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants, UV stabilizers.
  • additives such as, for example, surfactants, dispersants, fillers, setting agents, resins, waxes, defoamers, antidusting agents, extenders, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants, UV stabilizers.
  • Absorber and light stabilizers preferably in an amount of 0.1 to 10 wt .-%, in particular 0.5 to 5 wt .-%, based on the total weight of the pigment preparation.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic or amphoteric substances or mixtures of these agents.
  • Suitable anionic substances are, for example, fatty acid taurides, fatty acid N-methyltaurides, fatty acid isethionates, alkylphenylsulfonates, for example dodecylbenzenesulfonic acid, alkylnaphthalenesulfonates, alkylphenol polyglycol ether sulfates, fatty alcohol polyglycol ether sulfates, fatty acid amide polyglycol ether sulfates, alkyl sulfosuccinamates,
  • cation-active substances are, for example, quaternary ammonium salts, Fettaminoxalkylate, polyoxyalkyleneamines, alkoxylated polyamines,
  • Fatty amine polyglycol ethers for example alkyl, cycloalkyl or cyclized alkylamines, in particular fatty amines, di- and polyamines derived from fatty amines or fatty alcohols and their oxalkylates, fatty acid-derived imidazolines, polyaminoamido or polyamino 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.
  • alkyl, cycloalkyl or cyclized alkylamines in particular fatty amines, di- and polyamines derived from fatty amines or fatty alcohols and their oxalkylates, fatty acid-derived imidazolines, polyaminoamido or polyamino compounds or resins having an amine index between 100 and 800 mg KOH per g of the polyamin
  • Suitable nonionic and amphoteric substances are, for example, fatty amine carboxyglycinates, amine oxides, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, betaines 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 ,
  • epsilon-copper phthalocyanine can be kneaded with a crystalline inorganic salt in the presence of an organic solvent.
  • a crystalline inorganic salt in the presence of an organic solvent.
  • Such salt kneading are known to the person skilled in the art and are described, for example, in WO 02/04563 A1.
  • Pigment Blue 15: 6 is preferably subjected after filtration as a filter cake or as a dried material to a post-treatment for applying the pigment dispersant (II).
  • the invention also provides a process for the preparation of the pigment preparation according to the invention, which comprises reacting Cl. Pigment Blue 15: 6, if appropriate in the presence of the additive of the formula (3), (4) or (5), before, during or after kneading, wet grinding, dry grinding or finishing treatment with the pigment dispersant of the formula (II). Preference is given to the treatment of finely divided Pigment Blue 15: 6 after kneading, wet grinding, dry grinding or finish treatment with the pigment dispersant of the formula (II).
  • the dry components may be mixed in granule or powder form before or after grinding; the one component may be added to the other component in wet or dry form, for example by mixing the components in the form of wet
  • the mixing can be carried out, for example, by milling in dry form, in moist form, for example by kneading, or in suspension, or by a combination of these processes.
  • the grinding can with the addition of
  • the known drying units can be used, such as drying cabinets,
  • Paddle wheel dryers tumble dryers, contact dryers, belt dryers, spinflash dryers and spray dryers.
  • the pigment preparations of the invention can be used in principle for pigmenting all high molecular weight organic materials of natural or synthetic origin, for example of plastics, resins, paints, in particular metallic paints, paints, electrophotographic Toners and developers, electret materials, color filters and inks, inks.
  • hues in the blue range which are required when used in color filters can be achieved.
  • they ensure high contrast and also satisfy the other requirements imposed on color filters, such as high temperature stability or steep and narrow absorption bands.
  • the pigment preparations according to the invention are also suitable as colorants in aqueous-based and non-aqueous-based ink-jet inks and in inks which operate according to the hot-melt method.
  • the pigment preparations according to the invention are as 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, the may in turn be active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes, and as colorants for electronic inks ("e-inks”) or "electronic paper” (“e-inks”). paper ").
  • the pigmented color filters can also be applied by means of inkjet printing processes or other suitable printing processes.
  • the blue shades of the pigment preparations according to the invention are particularly well suited for the color filter color set red-green-blue (R, 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 blue color point are phthalocyanine colorants or benzimidazolone dioxazine pigments such as e.g. Cl. Pigment Blue 15: 6 and Cl. Pigment Blue 80.
  • phthalocyanine colorants are typically used, e.g. Cl. Pigment Green 36 and Cl. Pigment Green 7 and for the red color point are pyrrolopyrrole, quinacridone and azo pigments, such as. Cl. Pigment Red 254, Cl. Pigment Red 209, Cl. Pigment Red 175 and Cl. Pigment Orange 38, single or mixed, usual.
  • red and green hue is preferably mixed with yellow, for example with Cl. Pigment Yellow 138,139,150,151, 180 and 213.
  • blue hue is preferably mixed with Violet, z. With Cl. Pigment Violet 19 or 23.
  • a millbase is prepared. This is a 15% suspension of the pigment preparation in 66.25% PGMEA (propylene glycol monomethyl ether acetate), which in the presence of a commercially available, high molecular weight block copolymer (18.75% Disperbyk ® 161 or 2001, Byk Chemie) Paint Shaker (Disperse ® THE 200 from Lau GmbH) is dispersed for 5 h.
  • the millbase thus obtained is having a cone-plate viscometer Haake RS75 at 20 0 C measured (DIN 53019).
  • the stability of the Millbase is determined by measuring the viscosity after 7 days of storage.
  • the described Resinbase with the aid of a spin coater (POLOS Wafer Spinner) on glass plates (SCHOTT, laser-cut, 10 x 10 cm) applied and at a layer thickness of 500 to 1,300 nm, the contrast value (TSUBOSAKAELECTRIC CO. LTD, model CT-1) is measured.
  • the contrast values are normalized to a layer thickness of 1000 nm and compared relatively with each other (Table 2).
  • the particle size distribution For the particle size distribution, a series of electron micrographs is used. The primary particles are visually identified. The area of each primary particle is determined using a graphic tablet. From the area of the diameter of the same area circle is determined. The frequency distribution of the equivalent diameters thus calculated is determined and the frequencies are converted into volume fractions and displayed as a particle size distribution.
  • the d 50 value indicates the equivalent diameter, for which 50% of the counted particles are smaller.
  • the d g5 value is defined analogously.
  • a 2.5 L laboratory kneader (Werner & Pfleiderer) was determined with 187.5 parts commercial epsilon-copper phthalocyanine (d 50 > 100 nm, length / width> 5: 1), 1125 parts NaCl (mean particle size about 6 microns by laser diffraction) and 308 parts of diethylene glycol.
  • the mixture was kneaded at about 80 ° C for 24 h. After completion of the kneading, the kneading mass was stirred with 11.25 L of dilute hydrochloric acid (5% strength by weight) for 2 h at room temperature. After this solvent treatment, the suspension was filtered off and the filter cake was washed with water at 50 ° C. 676 parts of aqueous filter cake (pigment content 27%) were obtained. The filter cake was used to prepare the pigment preparation of the invention.
  • Example 2 Example 2:
  • Example 4 Analogously to Example 2, a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 0.8 part of 2-ethylhexylamine. After drying and pulverization, 43 parts of a pigment preparation (10% dispersant content) were obtained.
  • a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 0.62 part of n-hexylamine. After drying and pulverization, 43 parts of a pigment preparation (dispersant content 9.6%) were obtained.
  • a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 0.75 parts of 2-phenylethylamine. After drying and pulverization, 41 parts of a pigment preparation (9.9% dispersant content) were obtained.
  • a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 1.21 parts of dibenzylamine. After drying and pulverization, 40 parts of a pigment preparation (dispersant content 11%) were obtained.
  • Example 9 Analogously to Example 2, a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 2.17 parts of trioctylamine. After drying and pulverization, 44 parts of a pigment preparation (dispersant content 13.4%) were obtained.
  • Example 9 Example 9:
  • a pigment preparation was prepared from 40 parts of epsilon-copper phthalocyanine as filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 1.77 parts of tribenzylamine. After drying and pulverization, 45 parts of a pigment preparation (12.4% dispersant content) were obtained.
  • a pigment preparation was prepared from 40 parts of Cu phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 1.64 parts of oleylamine. After drying and pulverization, 45 parts of a pigment preparation (dispersant content 12.1%) were obtained.
  • Example 2 Analogously to Example 2, a pigment preparation of 40 parts of Cu phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 1, 8 parts of coconut oil bis (2-hydroxyethyl) amine was prepared. After drying and pulverization, 43 parts of a pigment preparation (dispersant content 11%) were obtained.
  • a pigment preparation was prepared from 40 parts of Cu phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 2.17 parts of triisooctylamine. After drying and pulverization, 45 parts of a pigment preparation (dispersant content 13.4%) were obtained.
  • Example 14 Analogously to Example 2, a pigment preparation of 40 parts of Cu phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 1, 82 parts of dehydroabietylamine was prepared. After drying and pulverization, 44 parts of a pigment preparation (dispersant content 12.5%) were obtained.
  • Example 14
  • Example 2 Analogously to Example 2, a pigment preparation of 40 parts of Cu phthalocyanine as a filter cake, 3.2 parts of copper phthalocyanine sulfonic acid and 0.81 parts of 6-aminohexanoic acid was prepared. After drying and pulverization, 41 parts of a pigment preparation (10% dispersant content) were obtained.
  • the mixture was stirred for a further 30 minutes at 60 0 C and the pigment suspension was filtered and washed at 50 0 C with deionized water. After drying in a convection oven at 80 ° C. (12 hours) and pulverizing in a powder mill, 44 parts of a pigment preparation (dispersant content: 11%) were obtained.
  • 146 parts of epsilon-copper phthalocyanine filter cake from Example 1 were dispersed in 700 parts of deionized water at 60 ° C. (pigment content of the suspension about 5%). Subsequently, a suspension of 1.8 parts of a copper phthalocyanine sulfonic acid (degree of sulfonation about 1.5) in 36 parts of deionized water / sodium hydroxide at a pH of 10.5 ⁇ 0.5 was added to the pigment suspension.

Landscapes

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

Abstract

La présente invention concerne de nouvelles préparations pigmentaires à particules fines comprenant comme pigment de base le pigment bleu C.I. 15:6 à particules fines et des dispersants de pigments de formule (II), ainsi que le procédé de production de ces préparations pigmentaires. Dans la formule (II), CPC représente un groupe d'une phtalocyanine de cuivre, n un nombre compris entre 0,1 et 4, de préférence entre 0,2 et 2, m un nombre compris entre 0,1 et 4, de préférence entre 0,2 et 2, Kat un cation du groupe des métaux alcalins ou H+ ; o un nombre compris entre 0 et 3,9, de préférence entre 0 et 1,8, avec n = m+o; R1, R2, R3 et R4 représentent chacun indépendamment l'hydrogène ou un groupe choisi parmi alkyle C1-C20, alcényle C2-C20, cycloalkyle C5-C20, cycloalcényle C5-C20 et alkyl-phényle C1-C4, les groupes susmentionnés étant éventuellement ramifiés et éventuellement substitués par des groupes sulfo, carboxy, hydroxy et des halogènes, à condition qu'un, deux ou trois des radicaux R1 à R4 représentent l'hydrogène.
EP08759258A 2007-07-17 2008-06-17 Préparations pigmentaires à base de pigment bleu c.i. 15:6 Withdrawn EP2167586A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102007033192A DE102007033192A1 (de) 2007-07-17 2007-07-17 Pigmentzubereitungen auf Basis von C.I. Pigment Blue 15:6
DE102008009194A DE102008009194A1 (de) 2008-02-15 2008-02-15 Pigmentzubereitungen auf Basis von C.I. Pigment Blue 15:6
PCT/EP2008/004854 WO2009010140A2 (fr) 2007-07-17 2008-06-17 Préparations pigmentaires à base de pigment bleu c.i. 15:6

Publications (1)

Publication Number Publication Date
EP2167586A2 true EP2167586A2 (fr) 2010-03-31

Family

ID=40260122

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08759258A Withdrawn EP2167586A2 (fr) 2007-07-17 2008-06-17 Préparations pigmentaires à base de pigment bleu c.i. 15:6

Country Status (7)

Country Link
US (1) US20100221654A1 (fr)
EP (1) EP2167586A2 (fr)
JP (1) JP2010533744A (fr)
KR (1) KR20100031618A (fr)
CN (1) CN101679767A (fr)
TW (1) TW200918610A (fr)
WO (1) WO2009010140A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008026584A1 (de) * 2008-06-03 2009-12-10 Clariant International Limited Verbessertes Cyanfarbmittel
WO2015015832A1 (fr) * 2013-07-31 2015-02-05 Dic株式会社 Composition de pigment phtalocyanine, procédé pour la fabriquer et encre
JP6498470B2 (ja) * 2015-02-20 2019-04-10 デクセリアルズ株式会社 透明導電膜およびその製造方法
CN106867273B (zh) * 2017-02-20 2019-05-03 宣城亚邦化工有限公司 用于聚乳酸体系着色的改性酞菁蓝颜料及其制备方法
WO2019124050A1 (fr) * 2017-12-22 2019-06-27 Dic株式会社 Composition de pigment phtalocyanine de cuivre et composition d'encre la contenant

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2218333B1 (fr) * 1973-02-21 1978-03-03 Ugine Kuhlmann
CA1088703A (fr) * 1976-09-21 1980-11-04 Ian R. Wheeler Substances pigmentaires
DE2906111C3 (de) * 1979-02-17 1984-02-09 Basf Ag, 6700 Ludwigshafen Pigmentzubereitungen für Druck- und Lackfarben
DE2906157A1 (de) * 1979-02-17 1980-09-04 Basf Ag Phthalocyaninzubereitungen
DE3211165A1 (de) * 1982-03-26 1983-09-29 Basf Ag, 6700 Ludwigshafen Pigmentzubereitungen und deren verwendung zum pigmentieren von tiefdruck- und lackfarben
JPH0753889A (ja) * 1993-08-10 1995-02-28 Toyo Ink Mfg Co Ltd 銅フタロシアニン顔料の製造方法および該製造方法より得られる銅フタロシアニン顔料を含む印刷インキもしくは塗料組成物
GB9517565D0 (en) * 1995-08-26 1995-10-25 Ciba Geigy Ag Pigment compositions
WO2000052103A1 (fr) * 1997-09-05 2000-09-08 Dainippon Ink And Chemicals, Inc. Composition pigmentaire, dispersion contenant une telle composition et resine coloree pour filtre colore
DE60102244T3 (de) * 2000-07-07 2007-09-20 Ciba Speciality Chemicals Holding Inc. Feste lösung von kupferphthalocyanin in pigmentform und transparente dispersion die diese enthält
WO2002048268A1 (fr) * 2000-12-13 2002-06-20 Ciba Specialty Chemicals Holding Inc. Ameliorateurs de rheologie et compositions pigmentaires ayant une rheologie amelioree
US7255733B2 (en) * 2003-06-20 2007-08-14 Toyo Ink Mfg. Co., Ltd. Process for the production of β type copper phthalocyanine pigment and a use thereof
JP4407175B2 (ja) * 2003-06-30 2010-02-03 東洋インキ製造株式会社 顔料分散体およびその使用
JP2005234009A (ja) * 2004-02-17 2005-09-02 Dainippon Ink & Chem Inc カラーフィルター用青色顔料組成物、その製造方法、およびそれを青色画素部に含有してなるカラーフィルター
DE102004010284A1 (de) * 2004-03-03 2005-09-22 Clariant Gmbh Pigmentzubereitungen auf Basis Phthalocyaninpigment
WO2007025932A2 (fr) * 2005-09-02 2007-03-08 Ciba Specialty Chemicals Holding Inc. Procede pour preparer une composition pigmentee destinee a des encres helio
JP4830648B2 (ja) * 2006-06-09 2011-12-07 富士ゼロックス株式会社 電子写真用トナー及び画像形成装置
CN101627089B (zh) * 2007-02-07 2013-08-21 西巴控股有限公司 蓝色酞菁颜料组合物及其制备

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2009010140A2 *

Also Published As

Publication number Publication date
CN101679767A (zh) 2010-03-24
TW200918610A (en) 2009-05-01
JP2010533744A (ja) 2010-10-28
WO2009010140A2 (fr) 2009-01-22
WO2009010140A3 (fr) 2009-07-02
US20100221654A1 (en) 2010-09-02
KR20100031618A (ko) 2010-03-23

Similar Documents

Publication Publication Date Title
EP1572810B8 (fr) Preparations de pigment de phtalocyanine
DE60117627T2 (de) Pigmentzusammensetzungen, deren Herstellungsverfahren, Farbmittel sowie gefärbte Artikel
EP1694777B1 (fr) Utilisation d'une preparation pigmentaire a base de pigment jaune c.i. 74
EP1940968B1 (fr) Préparations pigmentaires à base de dicétopyrrolopyrroles
EP2205682A2 (fr) Composition pigmentaire e base de dicetopyrrolopyrroles, destinee a etre utilisee dans des filtres colores
EP1723202A1 (fr) Preparations pigmentaires a base de pigments de phtalocyanine
EP2134794B1 (fr) Preparations pigmentaires a base de dicetopyrrolopyrroles
WO2009010140A2 (fr) Préparations pigmentaires à base de pigment bleu c.i. 15:6
WO2010091766A1 (fr) Préparations de pigment solide facilement dispersibles
EP2178985B1 (fr) Préparation pigmentaire à particules fines à base d'epsilon-phtalocyanine de cuivre
EP2121851A1 (fr) Composition d'epsilon-phtalocyanine de cuivre (pigment bleu 15:6) en fine particule destinée à être utilisée comme pigment
EP2486099A1 (fr) Préparation pigmentaire facilement dispersible à base de pigment c.i. jaune 155
DE102007033192A1 (de) Pigmentzubereitungen auf Basis von C.I. Pigment Blue 15:6
EP2134793B1 (fr) Procédé de production directe de pigments de dicétopyrrolopyrrole à fines particules
DE102008009194A1 (de) Pigmentzubereitungen auf Basis von C.I. Pigment Blue 15:6
WO2008107075A2 (fr) Préparations pigmentaires à base de dicétopyrrolopyrroles
WO2015135634A1 (fr) Composition de colorant à base de pyridone
DE102007049682A1 (de) Diketopyrrolopyrrol-Pigmentzusammensetzung zur Verwendung in Colorfiltern

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100217

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

RIN1 Information on inventor provided before grant (corrected)

Inventor name: METZ, THOMAS

Inventor name: PLUEG, CARSTEN

Inventor name: REICHWAGEN, JENS

17Q First examination report despatched

Effective date: 20110323

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20110419