US20010008912A1 - Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations - Google Patents

Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations Download PDF

Info

Publication number
US20010008912A1
US20010008912A1 US09/727,960 US72796000A US2001008912A1 US 20010008912 A1 US20010008912 A1 US 20010008912A1 US 72796000 A US72796000 A US 72796000A US 2001008912 A1 US2001008912 A1 US 2001008912A1
Authority
US
United States
Prior art keywords
pigment
formula
phenyl
alkyl
substituted
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.)
Abandoned
Application number
US09/727,960
Other languages
English (en)
Inventor
Joachim Weber
Felix Grimm
Erwin Dietz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Clariant GmbH filed Critical Clariant GmbH
Assigned to CLARIANT GMBH reassignment CLARIANT GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DIETZ, ERWIN, GRIMM, FELIX WENDELIN, WEBER, JOACHIM
Publication of US20010008912A1 publication Critical patent/US20010008912A1/en
Priority to US10/375,668 priority Critical patent/US7045638B2/en
Priority to US10/375,573 priority patent/US7045637B2/en
Priority to US10/807,634 priority patent/US7102014B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0034—Mixtures of two or more pigments or dyes of the same type
    • C09B67/0039—Mixtures of diketopyrrolopyrroles
    • 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
    • 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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes

Definitions

  • the present invention relates to novel pigment dispersants and pigment preparations having improved coloristic and rheological properties and to their preparation and use for pigmenting high molecular mass materials.
  • Pigment preparations are combinations of pigments and pigment dispersants that are structurally analogous to pigments and are substituted by groups having a specific activity.
  • the dispersants are added to the pigments in order to facilitate their dispersion in the application media, especially in varnishes, and to improve the rheological and coloristic properties of the pigments.
  • the viscosity of the highly pigmented paint concentrate (millbase) is lowered and the flocculation of the pigment particles reduced. This makes it possible, for example, to enhance the transparency and gloss. Such enhancement is particularly desirable in the case of metallic pigments.
  • EP-A-0 321 919 describes the production of pigment preparations by mixing the base pigments with pigment derivatives containing methyleneimidazolyl groups.
  • EP-A-0 877 058 describes the preparation of carboxamido-containing pigment dispersants, and pigment preparations comprising these pigment dispersants.
  • DE-A-3 106 906 describes the preparation of sulfonamido-containing pigment dispersants. Pigment dispersants based on diketopyrrolopyrrole compounds, however, are not mentioned.
  • JP H3-26767 describes sulfonamido-containing pigment dispersants based on diketopyrrolopyrrole compounds.
  • the pigment preparations produced with them do not meet every requirement imposed on pigment preparations in respect of the performance properties. For instance, their solvent fastness and fastness to overcoating is inadequate, so greatly restricting their universal application.
  • the invention provides pigment dispersants of the formula (I)
  • S is a number from 0.1 to 40
  • n is a number from 0 to 2
  • E + is H + or the equivalent M m+ /m of a metal cation M m+ from main groups 1 to 5 or transition groups 1 or 2 or 4 to 8 of the periodic system of the chemical elements, m being 1, 2 or 3, such as, for example, Li 1+ , Na 1+ , K 1+ , Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , Mn 2+ , Cu 2+ , Ni 2+ , Co 2+ , Zn 2+ , Fe 2+ , Al 3+ , Cr 3+ or Fe 3+ ; an ammonium ion N + R 9 R 10 R 11 R 12 , where the substituents R 9 , R 10 , R 11 and R 12 independently of one another are each a hydrogen atom, C 1 -C 30 -alkyl, C 2 -C 30 -alkenyl, C 5 -C 30 -cycloalkyl, phenyl, (C 1 -C 8 )-al
  • substituents R 9 and R 10 together with the quaternary nitrogen atom, are able to form a five- to seven-membered saturated ring system containing, if desired, further heteroatoms from the group consisting of O, S and N, said system being, for example, of the pyrrolidone, imidazolidine, hexamethyleneimine, piperidine, piperazine or morpholine type;
  • R 15 , R 16 , R 17 and R 18 independently of one another are hydrogen or a (poly)alkyleneoxy group of the formula —[CH(R 80 )—CH(R 80 )O] k —H, in which k is a number from 1 to 30 and the two radicals R 80 independently of one another are hydrogen, C 1 -C 4 -alkyl or, if k is>1, a combination thereof;
  • q is a number from 1 to 10, preferably 1, 2, 3, 4 or 5;
  • p is a number from 1 to 5, where p is ⁇ q+1;
  • T is a branched or unbranched C 2 -C 6 -alkylene radical; or in which T, if q is>1, may also be a combination of branched or unbranched C 2 -C 6 -alkylene radicals;
  • Z 1 is a radical of the formula (Ib)
  • X is a C 2 -C 6 -alkylene radical, a C 5 -C 7 -cycloalkylene radical, or a combination of these radicals, it being possible for these radicals to be substituted by from 1 to 4 C 1 -C 4 -alkyl radicals, hydroxyl radicals, (C 1 -C 4 )-hydroxyalkyl radicals and/or by 1 or 2 further C 5 -C 7 -cycloalkyl radicals, or in which X, if q is>1, may also be a combination of said definitions;
  • Y is a —O—
  • q is a number from 1 to 10, preferably 1, 2, 3, 4 or 5;
  • R 2 and R 3 independently of one another are a hydrogen atom, a substituted or unsubstituted, or partly fluorinated or perfluorinated, branched or unbranched (C 1 -C 20 )-alkyl group, a substituted or unsubstituted C 5 -C 7 -cycloalkyl group or a substituted or unsubstituted, or partly fluorinated or perfluorinated (C 2 -C 20 )-alkenyl group, it being possible for the substituents to be hydroxyl, phenyl, cyano, chloro, bromo, amino, C 2 -C 4 -acyl or C 1 -C 4 -alkoxy and to be preferably 1 to 4 in number, or
  • R 2 and R 3 together with the nitrogen atom, form a saturated, unsaturated or aromatic heterocyclic 5- to 7-membered ring containing, if desired, 1 or 2 further nitrogen, oxygen or sulfur atoms or carbonyl groups in the ring, being substituted if desired by 1, 2 or 3 of the radicals OH, phenyl, CN, Cl, Br, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -acyl and carbamoyl, and carrying, if desired, 1 or 2 benzo-fused saturated, unsaturated or aromatic, carbocyclic or heterocyclic rings;
  • Z 4 is hydrogen, hydroxyl, amino, phenyl, (C 1 -C 4 )-alkylene-phenyl, C 5 -C 7 -cycloalkyl or C 1 -C 20 -alkyl, it being possible for the phenyl ring, the (C 1 -C 4 )-alkylene-phenyl group and the alkyl group to be substituted by one or more, e.g., 1, 2, 3 or 4, substituents from the group consisting of Cl, Br, CN, NH 2 , OH, C 6 H 5 , mono-, di- or tri-C 1 -C 4 -alkoxy-substituted C 6 H 5 , carbamoyl, C 2 -C 4 -acyl and C 1 -C 4 -alkoxy, e.g., methoxy or ethoxy, and it being possible for the phenyl ring and the (C 1 -C 4 )-alkylene-phen
  • R 2 and R 3 independently of one another are a hydrogen atom, a C 1 -C 6 -alkyl group or a C 1 -C 6 -alkyl group substituted by 1 or 2 substituents from the group consisting of hydroxyl, acetyl, methoxy, ethoxy, chloro and bromo, or
  • R 2 and R 3 together with the adjacent nitrogen atom, form an imidazolyl, piperidinyl, morpholinyl, pipecolinyl, pyrrolyl, pyrrolidinyl, pyrazolyl, pyrrolidinonyl, indolyl or piperazinyl ring.
  • —(CH 2 ) 2 NH—CH 3 , —(CH 2 ) 2 —N(CH 3 ) 2 , —(CH 2 ) 2 —NH—CH 2 —CH 3 , —(CH 2 ) 2 —N(CH 2 —CH 3 ) 2 , —(CH 2 ) 3 —NH—CH 3 , —(CH 2 ) 3 —N(CH 3 ) 2 , —(CH 2 ) 3 —NH—CH 2 —CH 3 or —(CH 2 ) 3 —N(CH 2 —CH 3 ) 2 .
  • the pigment dispersants of the invention may be prepared by chlorosulfonating the diketopyrrolopyrrole compound of the formula (Ia)
  • amines of the formula (V) which may be used are ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine, isopentylamine, n-hexylamine, dimethylamine, diethylamine, dibutylamine, n-ethylbutylamine, ⁇ -hydroxyethylamine, ⁇ - or ⁇ -hydroxypropylamine, n-methylethanolamine, diethanolamine, 3-(2-hydroxyethylamino)-1-propanol, N-(2-hydroxyethyl)aniline, hydroxylamine, hydrazine, N,N-dimethyl-p-phenylenediamine, dimethylaminomethylamine, diethylaminoethylamine, 2-ethylhexylaminoethylamine, stearylaminoethylamine, oleyla
  • the chlorosulfonation is judiciously conducted using chlorosulfonic acid in a weight excess of from 4 to 25 times, based on the diketopyrrolopyrrole, and preferably further adding from 1 to 10 times the molar amount, based on the diketopyrroloyrrole, of thionyl chloride.
  • the chlorosulfonation is preferably conducted at a temperature of from ⁇ 10 to +150°C., in particular at from 0 to 100°C., under atmospheric or superatmospheric pressure.
  • the diketopyrrolopyrrole sulfochloride is judiciously precipitated in water and isolated.
  • the reaction of the sulfochloride with the amine takes place preferably at a temperature of from 0 to 100°C., in particular at from 0 to 70°C.
  • the molar amounts of amine:sulfochloride are judiciously (from 0.5 to 10):1, in particular (1 - 4):1.
  • the present invention further provides a pigment preparation comprising
  • base pigments organic pigments or mixtures of organic pigments which may also be present in the form of customary pigment preparations.
  • suitable base pigments for producing the pigment preparations of the invention are perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthanthrone, benzimidazolone, disazo condensation, azo, indanthrone, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, thioindigo, isoindoline, isoindolinone, pyranthrone, isoviolanthrone and carbon black pigments or mixtures thereof.
  • Examples of preferred base pigments for the purposes of the present invention are C.I. Pigment Red 123 (C.I. No. 71145), C.I. Pigment Red 149 (C.I. No. 71137), C.I. Pigment Red 178 (C.I. No. 71 155), C.I. Pigment Red 179 (C.I. No. 71 130), C.I. Pigment Red 190 (C.I. 71 140), C.I. Pigment Red 224 (C.I. No. 71 127), C.I. Pigment Violet 29 (C.I. No. 71 129), C.I. Pigment Orange 43 (C.I. No. 71 105), C.I. Pigment Red 194 (C.I.
  • Pigment Orange 42 C.I. Pigment Yellow 147, C.I. Pigment Red 168 (C.I. No. 59 300), C.I. Pigment Yellow 120 (C.I. No. 11 783), C.I. Pigment Yellow 151 (C.I. No. 13 980), C.I. Pigment Brown 25 (C.I. No. 12 510), C.I. Pigment Violet 32 (C.I. No. 12 517), C.I. Pigment Orange 64; C.I. Pigment Brown 23 (C.I. No. 20 060), C.I. Pigment Red 166 (C.I. No. 20 730), C.I. Pigment Red 170 (C.I. No. 12 475), C.I.
  • Pigment Orange 38 (C.I. No. 12 367), C.I. Pigment Red 188 (C.I. No. 12 467), C.I. Pigment Red 187 (C.I. No. 12 486), C.I. Pigment Orange 34 (C.I. No. 21 115), C.I. Pigment Orange 13 (C.I. No. 21 110), C.I. Pigment Red 9 (C.I. No. 12 460), C.I. Pigment Red 2 (C.I. No. 12 310), C.I. Pigment Red 112 (C.I. No. 12 340), C.I. Pigment Red 7 (C.I. No. 12 420), C.I. Pigment Red 210 (C.I. No.
  • C.I. Pigment Red 177 C.I. No. 65 300
  • C.I. Pigment Red 254 C.I. No. 56 110
  • C.I. Pigment Red 255 C.I. No. 56 1050
  • C.I. Pigment Red 264 C.I. Pigment Red 270
  • C.I. Pigment Red 272 C.I. No. 56 1150
  • C.I. Pigment Red 71 C.I. Pigment Orange 73
  • C.I. Pigment Red 88 C.I. No. 73 3112.
  • the pigment preparations of the invention may further comprise customary additives, such as fillers, standardizers, surfactants, resins, defoamers, antidust agents, extenders, shading colorants, preservatives, drying retarders, and rheology control additives, for example.
  • customary additives such as fillers, standardizers, surfactants, resins, defoamers, antidust agents, extenders, shading colorants, preservatives, drying retarders, and rheology control additives, for example.
  • Preferred pigment preparations for the purposes of the present invention consist essentially of
  • fractions of the respective components being based on the overall weight of the preparation (100% by weight).
  • Suitable surface-active agents c) include anionic or anion-active, cationic or cation-active, or nonionic substances or mixtures thereof.
  • suitable anionic substances are fatty acid taurides, fatty acid N-methyltaurides, fatty acid isethionates, alkylphenylsulfonates, alkylnaphthalenesulfonates, alkylphenol polyglycol ether sulfates, fatty alcohol polyglycol ether sulfates; fatty acids, e.g., palmitic, stearic and oleic acid; fatty acid amide polyglycol ether sulfates; alkylsulfosuccinamates; alkenylsuccinic monoesters, fatty alcohol polyglycol ether sulfosuccinates, alkanesulfonates, fatty acid glutamates, alkylsulfosuccinates, fatty acid sarco
  • Suitable cationic substances are quaternary ammonium salts, fatty amine oxalkylates, oxalkylated polyamines, fatty amine polyglycol ethers, fatty amines, diamines and polyamines derived from fatty amines or fatty alcohols, and the oxalkylates of these amines; imidazolines derived from fatty acids, and salts of these cationic substances.
  • nonionic substances are amine oxides, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, betaines, such as fatty acid amide N-propyl betaines, phosphoric esters of fatty alcohols or fatty alcohol polyglycol ethers, fatty acid amide ethoxylates, fatty alcohol-alkylene oxide adducts, and alkylphenol polyglycol ethers.
  • the pigment preparations of the invention generally comprise solid systems of free-flowing pulverulent consistency, or granules.
  • the dispersing effect which can be achieved in accordance with the invention is assumed to derive from a modification of the surface structure of the base pigments by the pigment dispersant as per b).
  • the efficacy of the pigment dispersant as per b) and the quality of the pigment preparations produced therewith are dependent on the point in time at which the pigment dispersant as per b) is added in the production process of the base pigment.
  • the dispersants may be added simultaneously or at different points in time or may be mixed prior to their addition.
  • the efficacy of the pigment dispersant as per b) may also depend on its particle size and particle morphology and on the extent of the available pigment surface. It may be advantageous to add the pigment dispersant as per b) to the base pigment only in the prospective application medium.
  • the optimum concentration of the pigment dispersant as per b) in each case must be determined by means of preliminary rangefinding tests, since the enhancement of the properties of the base pigments is not always in linear proportion to the amount of pigment dispersant.
  • the pigment preparations of the invention may comprise mixtures of one or more, preferably 1 or 2, base pigments with one or more, preferably 1 or 2, of the pigment dispersants as per b).
  • the invention also provides a process for producing a pigment preparation of the invention, which comprises mixing the pigment dispersant(s) as per (b) and the base pigment(s) with one another or causing them to act on one another at any desired point in time during their production process.
  • the production process of an organic pigment embraces its synthesis, possibly fine division, by grinding or reprecipitation, for example, possibly finishing, and its isolation as a presscake or in the form of dry granules or powder.
  • the pigment dispersant as per b) may be added prior to or during the pigment synthesis, immediately prior to or during the fine division process or a subsequent finishing.
  • the temperatures prevailing may be, for example, from 0 to 200° C.
  • the pigment dispersant as per b) can of course also be added in portions at different times.
  • the addition of the pigment dispersant as per b) as part of a fine division process takes place, for example, prior to or during the dry grinding of a crude pigment with or without additional milling auxiliaries on a roll mill or vibratory mill, or prior to or during the wet grinding of a crude pigment in an aqueous, aqueous-organic or organic grinding medium on, for example, a bead mill.
  • the pigment dispersant as per b) prior to or after finishing the base pigment in an aqueous, aqueous-alkaline, aqueous-organic or organic medium.
  • the pigment dispersant as per b) may also be added to the water-moist pigment presscake, and incorporated, before drying, in which case the pigment dispersant as per b) may itself be present as a presscake.
  • a further possibility is to make dry mixes of powders or granules of the pigment dispersant as per b) with the powder or granules of one or more base pigments, or to effect mixing by grinding or pulverizing components a) and b).
  • the pigment preparations of the invention are notable for their outstanding coloristic and rheological properties, especially for outstanding rheology, high flocculation stability, high transparency, ease of dispersibility, excellent gloss behavior, high color strength, excellent fastness to overcoating and to solvents, and very good weather fastness. They are suitable for use both in solventborne and aqueous systems.
  • the pigment preparations produced in accordance with the invention may be used to pigment high molecular mass organic materials of natural or synthetic origin, examples being plastics, resins, varnishes, paints, or electrophotographic toners and developers, and also writing, drawing and printing inks.
  • Examples of high molecular mass organic materials which may be pigmented with the abovementioned pigment preparations are cellulose ethers and cellulose esters, such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as addition-polymerization resins or condensation resins, e.g., amino resins, especially urea-formaldehyde and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins, polycarbonates, polyolefins, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylates, polyamides, polyurethanes or polyesters, rubber, casein, silicone and silicone resins, individually or in mixtures.
  • cellulose ethers and cellulose esters such as ethylcellulose, nitrocellulose, cellulose acetate or cellulose butyrate
  • the pigment preparations of the invention are used in an amount of from 0.05 to 30% by weight, preferably from 0.1 to 15% by weight.
  • the pigment preparations of the invention are also suitable for use as colorants in electrophotographic toners and developers, such as one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, polymerization toners, and specialty toners, for example (L. B. Schein, “Electrophotography and Development Physics”; Springer Series in Electrophysics 14, Springer Verlag, 2nd edition, 1992).
  • Typical toner binders are addition polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, and phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and also polyethylene and polypropylene, which may include further constituents, such as charge control agents, waxes or flow assistants, or may be modified subsequently with these additives.
  • polyaddition and polycondensation resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, and phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and also polyethylene and polypropylene, which may include further constituents, such as charge control agents, waxes or flow assistants, or may be modified subsequently with these additives.
  • the pigment preparations of the invention are suitable for use as colorants in powders and powder coating materials, especially in triboelectrically or electrokinetically sprayable powder coating materials, which are used to coat the surfaces of articles made, for example, of metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber (J. F. Hughes, “Electrostatics Powder Coating” Research Studies, John Wiley & Sons, 1984).
  • Typical powder coating resins used are epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane resins and acrylic resins, together with customary hardeners. Resin combinations are also used. For example, epoxy resins are frequently used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and also dicyandiamide and derivatives thereof, blocked isocyanates, bisacylurethanes, phenolic resins and melamine resins, triglycidyl isocyanurates, oxazolines, and dicarboxylic acids.
  • the pigment preparations of the invention are suitable for use as colorants in inkjet inks on either an aqueous or nonaqueous basis and in those inks which operate in accordance with the hot-melt process.
  • the pigment preparations of the invention are also suitable as colorants for color filters and for both additive and subtractive color generation.
  • the pigment dispersant as per b) it is also possible for the pigment dispersant as per b) to be added to the base pigment, or vice versa, only in the application medium.
  • the invention therefore further provides a prepared pigment formulation consisting essentially of one or more organic base pigments a), one or more pigment dispersants as per b), said high molecular mass organic material, especially varnish, and, if desired, surfactant and/or other customary additives.
  • the overall amount of base pigment plus pigment dispersant as per b) is, for example, from 0.05 to 30% by weight, preferably from 0.1 to 15% by weight, based on the overall weight of the prepared pigment formulation.
  • a four-necked flask is charged with 250 parts of chlorosulfonic acid, and 25 parts of 1,4-diketo-3,6-di(4-biphenyl)pyrrolo[3,4-c]pyrrole are introduced and dissolved at a rate such that the temperature does not exceed 25°C. Then 19.64 parts of thionyl chloride are added dropwise over the course of 15 min and the mixture is stirred for 15 min. Over the course of 15 min, the solution is added dropwise to 1000 parts of ice-water, prepared from 333 parts of ice and 667 parts of water. The precipitated sulfochloride is filtered and washed with 750 parts of cold water.
  • a four-necked flask is charged with 70 parts of ice, 70 parts of water and 15.3 parts of 3-dimethylamino-1-propylamine and the sulfochloride presscake is introduced at from 0 to 5° C.
  • the mixture is then stirred at 0 to 5° C. for 1 h, heated to 25° C. in 30 min, stirred at 25° C. for 30 min, heated to 50° C. in 30 min, stirred at 50° C. for 30 min, heated to 70° C. in 30 min and stirred at 70° C. for 30 min.
  • the product is filtered, washed with water and dried in a forced air oven at 80° C. This gives 39.9 parts of pigment dispersant. From the intensities of the 1 H-NMR signals, the degree of substitution s is calculated to be about 1.6.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the gloss measurement gives a value of 65.
  • the metallic coating is strongly colored and bright.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 21.63 parts of N-(3-aminopropyl)morpholine. This gives 42.1 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.7.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the viscosity is 2.6 s.
  • the gloss measurement gives a value of 75.
  • the metallic coating is strongly colored and bright.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 19.38 parts of N-(2-aminoethyl)piperazine. This gives 39.3 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.0.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 13.22 parts of 3-(methylamino)propylamine. This gives 36.1 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.2.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 15.62 parts of N-(2-aminoethyl)ethanolamine. This gives 37.5 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.2.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 28.5 parts of 3-(dibutylamino)-1-propylamine, 98% pure. This gives 47.4 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.9.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the rheology is evaluated as from 4 to 5 and the viscosity is 1.1 s.
  • the gloss measurement gives a value of 81.
  • the metallic coating is strongly colored and bright.
  • the HS coatings are weaker in color and substantially more hiding.
  • the rheology is evaluated as 3 and the viscosity is 16.5 s.
  • the gloss measurement gives a value of 52.
  • the metallic coating is markedly weaker in color and less bright.
  • the coating in the PE varnish is transparent and strongly colored.
  • the gloss measurement gives a value of 82.
  • the metallic coating is strongly colored and bright. Without the addition of the pigment dispersant, the PE coatings are weaker in color, markedly more hiding, and so matt that it is impossible to measure a gloss.
  • the metallic coating is significantly weaker in color and less bright.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 15.77 parts of 2-(2-aminoethoxy)ethanol . This gives 40.5 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.6.
  • Example I a The procedure of Example I a is repeated except that the amine used comprises 13.78 parts of 2-amino-1-butanol. This gives 36.6 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.4.
  • Example la The procedure of Example la is repeated except that the amine used comprises 21.33 parts of 1-(3-aminopropyl)-2-pyrrolidinone. This gives 42.2 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.6.
  • Example 1 a The procedure of Example 1 a is repeated except that the amine used comprises 19.54 parts of diethylaminopropylamine. This gives 41.3 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.7.
  • a pigment preparation is obtained whose solvent fastness is very good and which gives transparent and strongly colored coatings in the HS varnish.
  • the rheology is evaluated as 4-5 and the viscosity is 1.8 s.
  • the gloss measurement gives a value of 71.
  • the metallic coating is strongly colored and bright.
  • the HS coatings are weaker in color and substantially more hiding.
  • the rheology is evaluated as 3 and the viscosity is so high that it cannot be measured using the viscospatula.
  • the gloss as well is impossible to measure, owing to the severe flocculation.
  • the metallic coating is notably weaker in color and less bright.
  • the coating in the PE varnish is transparent and strongly colored.
  • the gloss measurement gives a value of 33.
  • the metallic coating is strongly colored and bright. Without the addition of the pigment dispersant, the PE coatings are weaker in color, markedly more hiding, and so matt that it is impossible to measure a gloss.
  • the metallic coating is significantly weaker in color and less bright.
  • the coating in the AM varnish is transparent and strongly colored.
  • the gloss measurement gives a value of 89.
  • the viscosity is 5.4 s.
  • the AM coatings are weaker in color, significantly more hiding and so matt that the gloss cannot be measured.
  • the viscosity is so high that it cannot be measured using the viscospatula.
  • the pigment dispersant of the formula XX is prepared as described in JP-H3-26767, Example 1.
  • the degree of substitution, s is calculated to be about 1.2.
  • a coating is prepared in the PE varnish using the pigment preparation prepared as in Example 10 c.
  • the fastness to overcoating is excellent, with no evidence of bleeding.
  • a coating is prepared in the PE varnish using the pigment preparation prepared as in Example 11 b.
  • the fastness to overcoating is deficient, with severe bleeding being visible.
  • a coating is prepared in the PUR varnish using the pigment preparation prepared as in Example 10 c.
  • the fastness to overcoating is excellent, with no evidence of bleeding.
  • a coating is prepared in the PUR varnish using the pigment preparation prepared as in Example 11 b.
  • the fastness to overcoating is unacceptable, with very severe bleeding being visible.
  • the pigment dispersant of the formula XX is prepared as per Example 10 a with the sole difference that, instead of 25 parts of 1,4-diketo-3,6-di-(4-biphenyl)pyrrolo[3,4-c] pyrrole, 16.4 parts of 1,4-diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole are used. This gives 17.2 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 0.12.
  • the solvent fastness of the pigment preparation is inadequate. In comparison to the solvent fastness of the pigment preparation of the formula XIX prepared in accordance with Example 10 a it is significantly poorer and thus distinctly inferior.
  • a coating is prepared in the PE varnish using the pigment preparation prepared as in Example 10 b.
  • the coating is transparent and strongly colored, the gloss measurement gives a value of 33.
  • the metallic coating is strongly colored and bright. The fastness to overcoating is excellent, with no evidence of bleeding.
  • a coating is prepared in the PE varnish using the pigment preparation prepared as in Example 13 b. Compared with the above coating, it is markedly more hiding, substantially weaker in color, the gloss is impossible to measure owing to the severe flocculation, and the metallic coating is substantially weaker in color and paler. The fastness to overcoating is deficient, with severe bleeding being visible.
  • a coating is prepared in the PUR varnish using the pigment preparation prepared as in Example 10 b.
  • the fastness to overcoating is excellent, with no evidence of bleeding.
  • a coating is prepared in the PUR varnish using the pigment preparation prepared as in Example 13 b.
  • the fastness to overcoating is unacceptable, with very severe bleeding being visible.
  • a coating is prepared in the HS varnish using the pigment preparation prepared as in Example 10 b. This coating is transparent and strongly colored. The rheology is assessed as from 4 to 5 and the viscosity is 1.8 s. The gloss measurement gives a value of 71. The metallic coating is strongly colored and bright. The fastness to overcoating is excellent.
  • a coating is prepared in the HS varnish using the pigment preparation prepared as in Example 13 b. Compared with the above coating, it is notably weaker in color. The rheology is evaluated as only 3 and the viscosity has increased to 3.0 s. The gloss measurement gives a value of only 43. The metallic coating is substantially weaker in color and paler. The test of fastness to overcoating shows marked bleeding.
  • a pigment preparation is obtained which gives coatings in the HS varnish which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Red 177), are more transparent, more glossy and distinctly stronger in color; the masstone coatings of the untreated standard commercial pigment (C.I. Pigment Red 177) show a haze.
  • the metallic coatings of the prepared pigment formulation are significantly cleaner and brighter than the metallic coatings of the untreated standard commercial pigment (C.I. Pigment Red 177).
  • the coatings of the pigment preparation are more transparent, substantially stronger in color and more glossy, and the metallic coatings are substantially stronger in color and brighter than the corresponding coatings of the untreated standard commercial pigment (C.I. Pigment Red 177).
  • a pigment preparation is obtained which in the HS varnish gives coatings which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Brown 25), are stronger in color.
  • the metallic coatings of the prepared pigment formulation are stronger in color and brighter.
  • a pigment preparation is obtained which in the HS varnish gives coatings which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Violet 23), are more transparent, stronger in color and substantially redder.
  • the metallic coatings of the prepared pigment formulation are stronger in color, brighter and substantially redder than the metallic coatings of the untreated standard commercial pigment (C.I. Pigment Violet 23).
  • the coatings of the pigment preparation are more transparent, stronger in color and markedly redder, and the metallic coatings are stronger in color and redder than the corresponding coatings of the untreated standard commercial pigment (C.I. Pigment Violet 23).
  • a pigment preparation is obtained which in the PE varnish gives coatings which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Violet 19, ⁇ -phase), are more transparent, stronger in color and cleaner.
  • the metallic coatings of the prepared pigment formulation are markedly stronger in color and brighter than the metallic coatings of the untreated standard commercial pigment (C.I. Pigment Violet 19, ⁇ -phase).
  • a pigment preparation is obtained which in the HS varnish gives coatings which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Blue 15:1), are more transparent, more glossy and stronger in color.
  • the metallic coatings of the prepared pigment formulation are stronger in color and brighter than the metallic coatings of the untreated standard commercial pigment (C.I. Pigment Blue 15:1).
  • the coatings of the pigment preparation are more transparent and the metallic coatings are substantially stronger in color and brighter than the corresponding coatings of the untreated standard commercial pigment (C.I. Pigment Blue 15:1).
  • a pigment preparation is obtained which in the HS varnish gives strongly colored and transparent coatings; the metallic coatings are strongly colored and bright.
  • a pigment preparation is obtained which in the HS varnish gives coatings which, compared with the coatings of the untreated standard commercial pigment (C.I. Pigment Red 179), are more transparent, more strongly colored and more glossy.
  • the metallic coatings of the prepared pigment formulation are more strongly colored and brighter.
  • a pigment preparation is obtained which in the HS varnish gives transparent and strongly colored coatings; the metallic coatings are strongly colored and bright.
  • a four-necked flask is charged with 250 parts of chlorosulfonic acid, and 25 parts of 1,4-diketo-3,6-di(4-biphenyl)pyrrolo[3,4-c]pyrrole are introduced and dissolved at a rate such that the temperature does not exceed 25°C. Then 19.64 parts of thionyl chloride are added dropwise over the course of 15 min and the mixture is stirred for 15 min. Over the course of 15 min, the solution is added dropwise to 1000 parts of ice-water, prepared from 333 parts of ice and 667 parts of water. The precipitated sulfochloride is filtered and washed with 750 parts of cold water.
  • a four-necked flask is charged with 70 parts of ice, 70 parts of water and 23.4 parts of N-cyclohexyl-1,3-propanediamine and the sulfochloride presscake is introduced at from 0 to 50° C.
  • the mixture is then stirred at 0 to 50° C. for 1 h, heated to 25°C. in 30 min, stirred at 25° C. for 30 min, heated to 50°C. in 30 min, stirred at 50° C. for 30 min, heated to 70°C. in 30 min and stirred at 70°C. for 30 min.
  • the product is filtered and washed with water.
  • the presscake is suspended in 782 parts of water and the pH of the suspension is adjusted to 8.6 using a little aqueous sodium hydroxide solution. Steam is passed through the suspension and condensed until about 860 parts of distillate have been obtained. The product is filtered, washed with water and dried in a forced air oven at 80°C. This gives 43.7 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.5.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the viscosity is 2.5 s.
  • the gloss measurement gives a value of 78.
  • the metallic coating is strongly colored and bright.
  • Example 24 a The procedure of Example 24 a is repeated except that the amine used comprises 22.3 parts of 2-(diisopropylamino)ethylamine. This gives 40.2 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.5.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the viscosity is 1.5 s.
  • the gloss measurement gives a value of 80.
  • the metallic coating is strongly colored and bright.
  • Example 24 a The procedure of Example 24 a is repeated except that the amine used comprises 24.5 parts of 2-amino-5-diethylaminopentane.
  • the presscake is suspended in 796 parts of water and the pH of the suspension is adjusted to 8.7 using a little aqueous sodium hydroxide solution. Steam is passed through the suspension and condensed until about 870 parts of distillate have been produced. The product is filtered, washed with water and dried at 80° C. in a forced air oven. This gives 41.6 parts of pigment dispersant.
  • the degree of substitution s is calculated to be about 1.7.
  • a pigment preparation is obtained which gives transparent and strongly colored coatings in the HS varnish.
  • the viscosity is 1.5 s.
  • the gloss measurement gives a value of 78.
  • the metallic coating is strongly colored and bright.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Paints Or Removers (AREA)
  • Optical Filters (AREA)
US09/727,960 1999-12-02 2000-12-01 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations Abandoned US20010008912A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US10/375,668 US7045638B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/375,573 US7045637B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/807,634 US7102014B2 (en) 1999-12-02 2004-03-24 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19958181A DE19958181A1 (de) 1999-12-02 1999-12-02 Pigmentdispergatoren auf Basis von Diketopyrrolopyrrolverbindungen und Pigmentzubereitungen
DE19958181.9 1999-12-02

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10/375,573 Continuation US7045637B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/375,668 Continuation US7045638B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations

Publications (1)

Publication Number Publication Date
US20010008912A1 true US20010008912A1 (en) 2001-07-19

Family

ID=7931228

Family Applications (4)

Application Number Title Priority Date Filing Date
US09/727,960 Abandoned US20010008912A1 (en) 1999-12-02 2000-12-01 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/375,573 Expired - Lifetime US7045637B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/375,668 Expired - Lifetime US7045638B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/807,634 Expired - Lifetime US7102014B2 (en) 1999-12-02 2004-03-24 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations

Family Applications After (3)

Application Number Title Priority Date Filing Date
US10/375,573 Expired - Lifetime US7045637B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/375,668 Expired - Lifetime US7045638B2 (en) 1999-12-02 2003-02-27 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US10/807,634 Expired - Lifetime US7102014B2 (en) 1999-12-02 2004-03-24 Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations

Country Status (7)

Country Link
US (4) US20010008912A1 (cs)
EP (1) EP1104789B1 (cs)
JP (1) JP2001214085A (cs)
KR (1) KR100722061B1 (cs)
CZ (1) CZ298015B6 (cs)
DE (2) DE19958181A1 (cs)
ES (1) ES2259968T3 (cs)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040035324A1 (en) * 2000-12-13 2004-02-26 Philippe Bugnon Rheology improvers and pigment compositions having improved rheology
WO2003066938A3 (en) * 2002-02-06 2004-07-29 Ciba Sc Holding Ag Process for the coloration of aluminium
US6827774B2 (en) 2000-12-13 2004-12-07 Ciba Specialty Chemicals Corporation Rheology improvers and pigment compositions having improved rheology
US20060052490A1 (en) * 2002-08-03 2006-03-09 Joachim Weber Pigment preparations based on diketopyrrolopyrrole pigments for the undistorted pigmentation of partially crystalline plastics
US20080308005A1 (en) * 2005-11-28 2008-12-18 Agfa Graphics Nv Non-Aqueous Pigment Dispersions Using Dispersion Synergists
US20090142681A1 (en) * 2005-10-21 2009-06-04 Tanja Reipen Pigment Preparations Based on Diketopyrrolopyrroles
US20100006009A1 (en) * 2008-07-08 2010-01-14 Clariant International Ltd. P.R. 254 Pigment Preparation for use in Color Filters
EP1650268A4 (en) * 2003-06-12 2010-01-20 Dainichiseika Color Chem HYDROPHILIC COLOR FOR IMAGE RECORDING, AQUEOUS COLOR FORMULATION FOR IMAGE RECORDING, METHOD AND DEVICE FOR IMAGE RECORDING
US20100121053A1 (en) * 2007-03-07 2010-05-13 Clariant Finance (Bvi) Limited Method For Directly Producing Fine-Particle Diketopyrrolopyrrol Pigments
US20100219384A1 (en) * 2007-10-17 2010-09-02 Clariant Finance (Bvi) Limited Diketopyrrolopyrrole Pigment Composition For Use In Color Filters

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0313924B1 (pt) * 2002-10-07 2013-06-25 revestimento, placa, folha, elemento de perfil ou moldagem, método de revestir um material, e composição de revestimento superficial
DE602006014231D1 (de) 2005-02-22 2010-06-24 Dainichiseika Color Chem Diketopyrrolopyrrole-Pigmentdispergatoren und ihre Verwendung
KR100694106B1 (ko) * 2005-04-27 2007-03-12 삼성전자주식회사 착색제 유사 첨가제를 함유한 잉크 조성물, 이를 포함한잉크젯 프린터 카트리지 및 잉크 젯트 기록 장치
DE102006007621A1 (de) * 2006-02-18 2007-08-23 Clariant International Limited Diketopyrrolopyrrol-Pigmente mit erhöhten Echtheiten und Verfahren zu deren Herstellung
KR101396904B1 (ko) * 2006-05-26 2014-05-19 토요잉크Sc홀딩스주식회사 안료 조성물의 제조 방법
DE102007011066A1 (de) 2007-03-07 2008-09-11 Clariant International Limited Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolen
DE102007011067A1 (de) 2007-03-07 2008-09-11 Clariant International Limited Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolen
WO2008134190A2 (en) 2007-04-24 2008-11-06 Sun Chemical Corporation Pigments for non-aqueous inks and coatings
WO2009026552A2 (en) * 2007-08-23 2009-02-26 Sensient Colors Inc. Self-dispersed pigments and methods for making and using the same
DE102007049682A1 (de) 2007-10-17 2009-04-23 Clariant International Ltd. Diketopyrrolopyrrol-Pigmentzusammensetzung zur Verwendung in Colorfiltern
DE102008032091A1 (de) 2008-07-08 2010-01-14 Clariant International Ltd. Diketopyrrolopyrrol-Mischpigmentzubereitung zur Verwendung in Colorfiltern
DE102008032092A1 (de) 2008-07-08 2010-01-14 Clariant International Ltd. Binäre Diketopyrrolopyrrol-Pigmentzusammensetzung zur Verwendung in Colorfiltern
EP2417202A2 (en) 2009-04-07 2012-02-15 Sensient Colors LLC Self-dispersing particles and methods for making and using the same
JP6543444B2 (ja) * 2014-08-07 2019-07-10 サカタインクス株式会社 カラーフィルター用赤色着色剤組成物
JP6570461B2 (ja) * 2016-03-03 2019-09-04 大日精化工業株式会社 顔料分散剤、顔料組成物、及び顔料着色剤
US10404923B1 (en) 2018-10-29 2019-09-03 Henry M. Pena Real time video special effects system and method
US10388322B1 (en) 2018-10-29 2019-08-20 Henry M. Pena Real time video special effects system and method
US11641439B2 (en) 2018-10-29 2023-05-02 Henry M. Pena Real time video special effects system and method
US11218646B2 (en) 2018-10-29 2022-01-04 Henry M. Pena Real time video special effects system and method
JP6928755B1 (ja) * 2020-03-13 2021-09-01 東洋インキＳｃホールディングス株式会社 顔料分散剤、カラーフィルタ用顔料組成物、着色組成物、およびカラーフィルタ

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US71483A (en) * 1867-11-26 Petek hend ricks
JPS56118462A (en) * 1980-02-25 1981-09-17 Toyo Ink Mfg Co Ltd Pigment composition
US4791204A (en) * 1985-11-26 1988-12-13 Ciba-Geigy Corporation 1,4-diketopyrrolo[3,4-c]pyrrole pigments
US4931566A (en) * 1987-07-31 1990-06-05 Ciba-Geigy Corporation Process for the preparation of pyrrolo[3,4-c]pyrroles
DE3838814A1 (de) * 1987-12-22 1989-07-06 Hoechst Ag Neue pigmente und ihre verwendung
DE3832064A1 (de) * 1988-09-21 1990-03-29 Hoechst Ag Verfahren zur herstellung von pigmentzubereitungen der anthanthronreihe
US5261032A (en) * 1988-10-03 1993-11-09 Robert Rocchetti Method for manipulation rectilinearly defined segmnts to form image shapes
DE4011927A1 (de) 1989-04-17 1990-10-18 Ciba Geigy Ag Verwendung von pyrrolo-pyrrol-verbindungen zum faerben und bedrucken von fasermaterialien
JP2584515B2 (ja) * 1989-06-23 1997-02-26 東洋インキ製造株式会社 顔料分散剤および顔料組成物
EP0538784B2 (de) * 1991-10-23 2000-12-27 Clariant GmbH Pigmentzubereitungen
TW247315B (cs) * 1992-12-18 1995-05-11 Ciba Geigy
DE4325247A1 (de) * 1993-07-28 1995-02-02 Basf Ag Pigmentzubereitungen mit Perylenderivaten als Dispergiermitteln
SE501793C2 (sv) 1993-10-08 1995-05-15 Perstorp Ab Användning av inositoltrisfosfat för beredning av läkemedel
TW370546B (en) * 1995-09-18 1999-09-21 Ciba Sc Holding Ag Solid solutions of 1,4-diketopyrrolopyrroles
DE19620746A1 (de) * 1996-05-23 1997-11-27 Hoechst Ag Farbige Monomere enthaltende chirale cLCPs
DE59804631D1 (de) * 1997-05-06 2002-08-08 Ciba Sc Holding Ag Diketopyrrolopyrrolzusammensetzungen
US6057449A (en) * 1998-06-02 2000-05-02 Ciba Specialty Chemicals Corporation Direct preparation of pyrrolo[3,4-c]pyrroles
DE19906494A1 (de) * 1999-02-17 2000-08-24 Clariant Gmbh Pigmentzubereitungen auf Basis von Diketopyrrolopyrrolpigmenten mit basischen Perylendispergatoren
DE10028104A1 (de) 2000-06-07 2001-12-13 Clariant Gmbh Verfahren zur Herstellung von Diketopyrrologyrrol-Pigmenten

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040035324A1 (en) * 2000-12-13 2004-02-26 Philippe Bugnon Rheology improvers and pigment compositions having improved rheology
US6827774B2 (en) 2000-12-13 2004-12-07 Ciba Specialty Chemicals Corporation Rheology improvers and pigment compositions having improved rheology
US6827775B2 (en) 2000-12-13 2004-12-07 Ciba Specialty Chemicals Corporation Rheology improvers and pigment compositions having improved rheology
WO2003066938A3 (en) * 2002-02-06 2004-07-29 Ciba Sc Holding Ag Process for the coloration of aluminium
US20050155162A1 (en) * 2002-02-06 2005-07-21 Hans-Thomas Schacht Process for the coloration of aluminium
US20060052490A1 (en) * 2002-08-03 2006-03-09 Joachim Weber Pigment preparations based on diketopyrrolopyrrole pigments for the undistorted pigmentation of partially crystalline plastics
US7153358B2 (en) 2002-08-03 2006-12-26 Clariant Gmbh Pigment preparations based on diketopyrrolopyrrole pigments for the undistorted pigmentation of partially crystalline plastics
US20080194742A1 (en) * 2002-08-03 2008-08-14 Matthias Ganschow Method for Undistorted Pigmentation of Partially Crystalline Plastics
EP1650268A4 (en) * 2003-06-12 2010-01-20 Dainichiseika Color Chem HYDROPHILIC COLOR FOR IMAGE RECORDING, AQUEOUS COLOR FORMULATION FOR IMAGE RECORDING, METHOD AND DEVICE FOR IMAGE RECORDING
US20090142681A1 (en) * 2005-10-21 2009-06-04 Tanja Reipen Pigment Preparations Based on Diketopyrrolopyrroles
US20090048375A1 (en) * 2005-11-28 2009-02-19 Agfa Graphics Nv Non-Aqueous Pigment Dispersions Using Dispersion Synergists
US7632346B2 (en) * 2005-11-28 2009-12-15 Agfa Graphics Nv Non-aqueous pigment dispersions using dispersion synergists
US7648572B2 (en) 2005-11-28 2010-01-19 Agfa Graphics Nv Non-aqueous pigment dispersions using dispersion synergists
US20080308005A1 (en) * 2005-11-28 2008-12-18 Agfa Graphics Nv Non-Aqueous Pigment Dispersions Using Dispersion Synergists
US20100121053A1 (en) * 2007-03-07 2010-05-13 Clariant Finance (Bvi) Limited Method For Directly Producing Fine-Particle Diketopyrrolopyrrol Pigments
US7967906B2 (en) 2007-03-07 2011-06-28 Clariant Finance (Bvi) Limited Method for directly producing fine-particle diketopyrrolopyrrol pigments
US20100219384A1 (en) * 2007-10-17 2010-09-02 Clariant Finance (Bvi) Limited Diketopyrrolopyrrole Pigment Composition For Use In Color Filters
US8128848B2 (en) 2007-10-17 2012-03-06 Clariant Finance (Bvi) Limited Diketopyrrolopyrrole pigment composition for use in color filters
US20100006009A1 (en) * 2008-07-08 2010-01-14 Clariant International Ltd. P.R. 254 Pigment Preparation for use in Color Filters
US7892344B2 (en) * 2008-07-08 2011-02-22 Clariant Finance (Bvi) Limited P.R. 254 pigment preparation for use in color filters

Also Published As

Publication number Publication date
DE50012474D1 (de) 2006-05-18
US7045638B2 (en) 2006-05-16
US7045637B2 (en) 2006-05-16
CZ298015B6 (cs) 2007-05-23
EP1104789B1 (de) 2006-03-29
ES2259968T3 (es) 2006-11-01
KR20010062074A (ko) 2001-07-07
CZ20004460A3 (cs) 2001-09-12
DE19958181A1 (de) 2001-06-07
KR100722061B1 (ko) 2007-05-25
EP1104789A2 (de) 2001-06-06
US20030162976A1 (en) 2003-08-28
US20030162977A1 (en) 2003-08-28
US7102014B2 (en) 2006-09-05
JP2001214085A (ja) 2001-08-07
EP1104789A3 (de) 2003-10-29
US20040177790A1 (en) 2004-09-16

Similar Documents

Publication Publication Date Title
US7045638B2 (en) Pigment dispersants based on diketopyrrolopyrrole compounds and pigment preparations
US6221150B1 (en) Perylene compounds and pigment preparations
US6918958B2 (en) Acid pigment dispersants and pigment preparations
US5248774A (en) Inner salts based on ammonium and sulfonate groups of perylene-3,4,9,10-tetracarboxylic and derivatives thereof
US7459016B2 (en) Method for the production of phthalocyanine pigment preparations
US5958129A (en) Pigment formulations and processes for their preparation
US6409816B1 (en) Pigment preparations based on diketopyrrolopyrrole pigments with basic perylene dispersants
US6413309B1 (en) Pigment preparations comprising two or more perylene compounds
US20090142681A1 (en) Pigment Preparations Based on Diketopyrrolopyrroles
US6174361B1 (en) Process for preparing N,N′-dimethylperylene-3,4,9,10-tetracarboxylic diimide in transparent pigment form
US6646126B2 (en) Process for preparing perylene-3,4,9,10-tetracarboxylic diimide in transparent pigment form
US20060135774A1 (en) Method for producing pigment transparent preparations based on perylene-3,4,9,10-tetracarboxylic acid diimine
DE19835757A1 (de) Perylenverbindungen und Pigmentzubereitungen

Legal Events

Date Code Title Description
AS Assignment

Owner name: CLARIANT GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WEBER, JOACHIM;GRIMM, FELIX WENDELIN;DIETZ, ERWIN;REEL/FRAME:011345/0385

Effective date: 20001115

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION