EP1517962A1 - Procede pour produire des pigments disazoiques - Google Patents

Procede pour produire des pigments disazoiques

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Publication number
EP1517962A1
EP1517962A1 EP03735467A EP03735467A EP1517962A1 EP 1517962 A1 EP1517962 A1 EP 1517962A1 EP 03735467 A EP03735467 A EP 03735467A EP 03735467 A EP03735467 A EP 03735467A EP 1517962 A1 EP1517962 A1 EP 1517962A1
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EP
European Patent Office
Prior art keywords
parts
finish
organic solvent
amino
methyl
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Withdrawn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
EP03735467A
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German (de)
English (en)
Inventor
Olaf Schupp
Felix W. Grimm
Manfred Opravil
Joachim Weber
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
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Filing date
Publication date
Application filed by Clariant GmbH filed Critical Clariant GmbH
Publication of EP1517962A1 publication Critical patent/EP1517962A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)

Definitions

  • the present invention relates to a new process for the preparation of disazo pigments with heterocyclic bases as the diazo component.
  • Some disazo pigments occur in their synthesis as finely divided prepigments that when sintered they sinter to hard and coarse-grained powders that can no longer be satisfactorily dispersed. In order to bring them into a form that can be used in application technology, the fine particles have to be subjected to a crystal growth process by means of a finish.
  • DE-A-24 51 097 discloses disazo pigments with heterocyclic bases as the diazo component and a process for the preparation of these disazo pigments.
  • DE-A-23 29 781 discloses disazo pigments with aminobenzoxazinediones as the diazo component. Pigments in this class have low color strengths.
  • DE-A-42 25 295 discloses disazo pigments with aminophenyl-benzothiazole as the diazo component. Pigments in this class have poor lightfastness.
  • DE-A-42 29 207 discloses a process for producing disazo pigments, characterized in that a surfactant with a cloud point is used.
  • the use of the pigments produced according to the invention is limited to use in printing inks.
  • coloring plastics in addition to the coloristics and fastness properties such as fastness to bleeding, good dispersibility is particularly required.
  • high color strengths and gloss are decisive in printing systems.
  • the pigments should be used as universally as possible.
  • the disazo pigments prepared by the known processes with heterocyclic bases as the diazo component partly do not meet today's requirements, and partly they are not universally applicable.
  • the object is achieved by a finish in aqueous-organic solvent at neutral or alkaline pH, or in organic solvent at alkaline pH.
  • the invention relates to a process for the preparation of disazo pigments of the general formula (I)
  • R 1 and R 2 are the same or different and are hydrogen, CC 4 alkyl, CC 4 alkoxy, Ci-Cs-alkoxycarbonyl, nitro, cyano, halogen, phenoxy or trifluoromethyl;
  • D 1 and D 2 are the same or different and are an aromatic heterocycle from the group benzimidazole, benzimidazolone, benzimidazolthione, benzoxazole, benzoxazolone, benzothiazolone, indazole, phthalimide, naphthalimide, benzotriazole, quinoline, benzodiazines, phenmorpholine, benzmidoline, phenmorpholinone indolone, benzimidazo [1, 2-a] pyrimidone,
  • Carbazole and indole wherein said heterocycles are unsubstituted or by 1, 2, 3 or 4 identical or different radicals from the group halogen, C 1 -C 4 alkyl, acetamido, carbomethoxyamino, CrC alkoxy, nitro, phenyl, phenoxy or Trifluoromethyl are substituted, where the phenyl radical can be substituted by chlorine, methyl or methoxy; and wherein said heterocycle is linked directly or through a phenylene group to the azo group in formula (I);
  • Coupling product is subjected to a finish in organic solvent at alkaline pH, or in aqueous-organic solvent at neutral or alkaline pH.
  • R 1 and R 2 are preferably identical or different and are hydrogen, methyl, ethyl, methoxy, ethoxy, propoxy, butoxy, fluorine, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl or trifluoromethyl.
  • Preferred aromatic heterocycles are those from the group benzimidazolone, phthalimide, naphthalimide and benzodiazines, such as quinazoline, quinazolinone, quinazolinedione, phthalazine, phthalazinone, phthalazinedione, quinoxaline, quinoxalinone and quinoxalinedione.
  • the heterocycles D 1 and D 2 are preferably unsubstituted or substituted by 1, 2 or 3 identical or different radicals from the group methyl, ethyl, methoxy, ethoxy, nitro, fluorine, chlorine, bromine, phenyl or trifluoromethyl.
  • the general formula (I) is to be understood as an idealized formula and also includes the corresponding tautomeric compounds and the possible ones Configuration isomers of any tautomeric form. In the rings of D 1 and D 2, for example, -NH-CO groups can also be present in various tautomeric forms.
  • the disazo pigments of the general formula (I) are normally in the hydrazone form.
  • the general formula (I) therefore primarily includes the bishydrazone form.
  • the coupling product is expediently azo-coupled from one or more diazotized amines of the formula D-NH 2 , in which D has the abovementioned meaning D 1 or D 2 , advantageously with 0.45 mol to 0.55 mol, preferably 0.5 to 0, 53 mol, per mol of the total diazonium salts to be reacted, one or more coupling components of the general formula (III)
  • R 1 and R 2 have the meaning given above.
  • Coupling products which are prepared by coupling only a diazotized amine of the formula D-NH 2 are preferably used, so that pigments of the general formula (I) are obtained in which D 1 and D 2 have the same meaning.
  • R 1 and R 2 are the same or different and are hydrogen, methyl, methoxy, chlorine or trifluoromethyl, so that pigments of the general formula (I) are obtained in which D 1 and D 2 have the same meaning.
  • amines of the formula D-NH 2 are heterocyclic amines from the group benzimidazole, benzimidazolone, benzimidazolthione, benzoxazole, benzoxazolone, benzothiazolone, indazole, phthalimide, naphthalimide, benzotriazole, quinoline, benzodiazines, such as quinazoline, quinazolinone, quinazoline, quinazolinone, quinazolinone, Phthalazinedione, quinoxaline, quinoxalinone and quinoxalinedione, phenmorpholine, phenmorpholinone, benzo [c, d] indolone, benzimidazo [1,2-a] pyrimidone, carbazole and indole, where the heterocycles can be unsubstituted or substituted by the radicals mentioned above, for example 4 -Amino-6-chlorobenzimidazole, 4-a
  • amines of the formula D-NH 2 are 5-aminobenzimidazol-2-one, which in the 6-position additionally by methyl, methoxy, chlorine, nitro or trifluoromethyl and in the 1- and / or 3-position additionally by methyl or Ethyl may be substituted; 6-aminoquinoxaline-2,3-dione, which can additionally be substituted in the 7-position by methyl, methoxy, chlorine, nitro or trifluoromethyl and in the 1- and / or 4-position additionally by methyl or ethyl, 6-aminoquinazoline-2 , 4-dione, which is additionally in the 7-position by methyl, Methoxy, chlorine, nitro or trifluoromethyl and in the 1- and / or 3-position can additionally be substituted by methyl or ethyl.
  • Examples of coupling components are 1, 4-bis (acetoacetylamino) benzene, 2-fluoro-1, 4-bis (acetoacetylamino) benzene, 2-chloro-1, 4-bis (acetoacetylamino) benzene, 2-bromo-1, 4 bis (acetoacetylamino) benzene, 2-trifluoromethyl-1,4-bis (acetoacetylamino) benzene, 2-cyano-1,4, bis (acetoacetylamino) benzene, 2-methyl-1,4, bis (acetoacetylamino) benzene , 2-methoxy-1,4-bis (acetoacetylamino) benzene, 2-ethoxy-1,4-bis (acetoacetylamino) benzene, 2-phenoxy-1,4, bis (acetoacetylamino) benzene, 2-nitro-1,4 bis (acetoacetylamino) benzene,
  • Particularly preferred coupling components are 1,4-bis (acetoacetylamino) benzene, 2-methyl-1,4-bis (acetoacetylamino) benzene, 2,5-dimethyl-1,4-bis (acetoacetylamino) benzene, 2-chloro-1 , 4-bis (acetoacetylamino) benzene,
  • the coupling product can be prepared by one of the customary methods, for example in an aqueous medium by means of an azo coupling reaction, by adding a) the diazonium salt to the coupling component (direct coupling) or b) the coupling component to the diazonium salt (indirect coupling), or c) it can also the diazonium salt and the coupling component by means of a mixing nozzle, a microreactor or a microjet reactor can be mixed with one another by simultaneous, continuous feeding.
  • Both the diazonium salt and the coupling component can be dissolved or used as a suspension, in the case of indirect coupling it is also customary to add the coupling component in solid form.
  • the coupling component is preferably added as a freshly precipitated suspension to the diazonium salt present as a solution or suspension. It may be advantageous to carry out the coupling in the presence of customary coupling-promoting agents, such as, for example, long-chain amine oxides and phosphine oxides.
  • Couplings in aqueous-organic or purely organic solvents can also be used to produce the coupling products.
  • the process parameters essential for azo coupling such as time, temperature, pH, use of buffers, solvents or surfactants, are known to the person skilled in the art from the literature. Usual pH values are 2 to 10. Usual temperatures are 0 to 75 ° C.
  • the coupling product used in the process according to the invention can be used both in the form of a press cake, preferably an aqueous-moist press cake, and in the dried state, for example as granules or powder.
  • the finish of the coupling product is preferably carried out in a suspension which contains 1 to 50% by weight, preferably 2 to 20% by weight, in particular 3 to 17.5% by weight, of the coupling product, based on the total weight the suspension.
  • 1 to 50% by weight preferably 2 to 20% by weight, in particular 3 to 17.5% by weight
  • Larger amounts of solvent can be used, but this can become uneconomical. With smaller amounts of solvent, the stirrability of the mixture can be impaired.
  • Organic solvents for the finish are alcohols with 1 to 20, especially 1 to 10, carbon atoms, such as, for example, methanol, ethanol, n-propanol, isopropanol, butanols, such as n-butanol, iso-butanol, tert-butanol, pentanols , such as n-pentanol, 2-methyl-2-butanol, hexanols, such as 2-methyl-2-pentanol, 3-methyl-3-pentanol, 2-methyl-2-hexanol, 3-ethyl-3-pentanol, octanols such as 2,4,4-trimethyl-2-pentanol, cyclohexanol; or glycols, such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, or glycerin; Polyglycols, such as polyethylene or polypropylene glycols; Et
  • Sulfoxides such as dimethyl sulfoxide and sulfolane; as well as mixtures of these solvents.
  • the solvent is stable under the selected conditions.
  • aqueous-organic solvent at least 2.5% by weight, preferably at least 5% by weight, in particular at least 7.5% by weight, of the liquid phase is expediently organic solvent.
  • Particularly preferred solvents are CrC ⁇ alcohols, in particular methanol, ethanol, isopropanol, isobutanol and tert-butanol and tert-amyl alcohol, or butyl glycol, dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone or dimethyl sulfoxide.
  • aqueous-organic solvent with 2.5 to 95% by weight, preferably 5 to 90% by weight, in particular 7.5 to 75% by weight, organic solvent, based on the total weight of the liquid phase, is preferred.
  • the setting of an alkaline pH causes a change in the tautomeric form of the coupling product, but depending on the amount of base and the nature of the liquid phase, one or even multiple deprotonation of the coupling product with salt formation can also take place. Both are generally visible through a color change.
  • the bases are alkali metal hydroxides, optionally in the form of their aqueous solutions, such as sodium or potassium hydroxide, or alkali metal alcoholates, where alkali is in particular sodium or potassium, and the alcoholate is preferably derived from d-C ⁇ alcohols, such as for example sodium or potassium methanolate, ethanolate, isopropoxide, tert-butoxide and tert-amylate, are used.
  • the alkali metal alcoholates can also be prepared in situ by reacting the corresponding alcohol with the alkali metal, alkali metal hydride or alkali metal amide.
  • the amount of base used can vary over a wide range.
  • the base can also be used in larger amounts for salt formation, for example 0.5 to 20 mol, preferably 0.5 to 15 mol, in particular 0.5 to 10 mol, based on 1 mol of the pigment.
  • An aqueous-organic medium is preferably chosen at neutral or alkaline pH.
  • the finish in the process according to the invention is preferably at a temperature of 0 to 250 ° C., particularly 15 to 200 ° C., in particular 50 to 190 ° C., for a time of 5 minutes to 96 hours, particularly 5 minutes to 48 hours, in particular 5 Minutes to 24 hours, optionally carried out under increased pressure.
  • Organic acids such as e.g. aliphatic or aromatic carboxylic or sulfonic acids, such as formic acid, acetic acid, propionic acid, butyric acid, hexanoic acid, oxalic acid, citric acid, benzoic acid, phenylacetic acid, benzenesulfonic acid or p-toluenesulfonic acid, and inorganic acids such as e.g. Hydrochloric acid, sulfuric acid or phosphoric acid.
  • Organic acids such as e.g. aliphatic or aromatic carboxylic or sulfonic acids, such as formic acid, acetic acid, propionic acid, butyric acid, hexanoic acid, oxalic acid, citric acid, benzoic acid, phenylacetic acid, benzenesulfonic acid or p-toluenesulfonic acid, and inorganic acids such as e.g. Hydrochloric acid, sulfuric acid
  • the pigments are isolated in the usual way by filtration. Before the pigment is isolated, any solvent which may be used can be distilled, if appropriate under reduced pressure, or else by
  • the pigments produced by the process according to the invention can be used as preferably aqueous presscakes, but as a rule they are solid systems of free-flowing, powdery nature or granules.
  • auxiliaries such as, for example, surfactants, pigmentary and non-pigmentary dispersants, fillers, fillers, resins, waxes, defoamers, anti-dusting agents, extenders, colorants for shading, preservatives, drying retardants, additives for controlling the rheology, Wetting agents, antioxidants, such as flame retardants or deflagration-inhibiting agents, UV absorbers, light stabilizers, or a combination thereof can be used.
  • Auxiliaries can be added at any time before, during or after the finish or grinding or after isolation, all at once or in several portions.
  • the total amount of auxiliaries added can be 0 to 40% by weight, preferably 1 to 30% by weight, particularly preferably 2.5 to 25% by weight, based on the pigment.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic substances or mixtures of these agents.
  • anionic substances are fatty acid taurides, fatty acid N-methyl taurides, fatty acid isethionates, alkylphenyl sulfonates, alkylnaphthalenesulfonates, alkylphenol polyglycol ether sulfates,
  • Naphthenic acids and resin acids for example abietic acid, alkali-soluble resins, for example rosin-modified maleate resins and condensation products based on cyanuric chloride, taurine, N, N'-diethylaminopropylamine and p-phenylenediamine.
  • Resin soaps i.e. Alkaline salts of resin acids.
  • Quaternary ammonium salts fatty amine oxyalkylates, oxyalkylated polyamines, fatty amine polyglycol ethers, fatty amines, di- and polyamines derived from fatty amines or fatty alcohols, and the like, come as cation-active substances Oxalkylates, imidazolines derived from fatty acids, and salts of these cation-active substances, such as, for example, acetates.
  • nonionic substances are amine oxides, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, betaines such as fatty acid amide-N-propyl-betaine, phosphoric acid esters of aliphatic and aromatic alcohols, fatty alcohols or fatty alcohol polyglycol ethers, fatty acid amide ethoxylates, fatty alcohol-alkylene oxide adducts and alkylphenol adducts and alkylphenol into adducts and alkylphenol.
  • Nonpigmentary dispersants mean substances that are not structurally derived from organic pigments by chemical modification. They are added as dispersants either already during the production of pigments, but often also when the pigments are incorporated into the application media to be colored, for example in the production of lacquers or printing inks by dispersing the pigments in the corresponding binders.
  • Polymeric substances for example polyolefins, polyesters, polyethers, polyamides, polyimines, polyacrylates, polyisocyanates, block copolymers thereof, copolymers of the corresponding monomers or polymers of one class which have been modified with a few monomers of another class.
  • Non-pigmentary dispersants can furthermore also be aromatic substances which are chemically modified with functional groups and are not derived from organic pigments.
  • Nonpigmentary dispersants are known in the art and some are available commercially (for example, Solsperse ®, Avecia; Disperbyk ®, Byk, Efka ®, Efka).
  • These basic structures are often further modified, for example by chemical reaction with other functional groups or by salt formation.
  • pigmentary dispersants are meant pigment dispersants which are derived from an organic pigment as the base body and are produced by chemical modification of this base body, for example saccharin-containing pigment dispersants, piperidyl-containing pigment dispersants, naphthalene or perylene-derived pigment dispersants, pigment dispersants with functional groups which have a methylene group with the Basic pigment bodies are linked, chemically modified basic pigment bodies, pigment dispersants containing sulfonic acid, sulfonamide or sulfonic acid ester groups, pigment dispersants containing ether or thioether groups, or pigment dispersants containing carboxylic acid, carboxylic acid ester or carbonamide groups.
  • auxiliaries is not absolutely necessary in the process according to the invention for the preparation of the disazo pigments.
  • disazo pigments according to the invention are not restricted to one area of application.
  • they are characterized by excellent application properties, in particular by very good dispersibility, good rheology, high color strength, perfect bleeding and bleeding Fastness to overcoating and very good light and weather fastness.
  • opaque or transparent pigments can be produced and the color tone can be varied.
  • the pigments produced by the process according to the invention can be used for pigmenting high molecular weight organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints or electrophotographic toners and developers, as well as inks and printing inks.
  • High molecular weight organic materials that can be pigmented with the pigments mentioned are, for example, cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, cellulose acetate or cellulose butyrate, natural resins or synthetic resins, such as polymerization resins or condensation resins, for example aminoplasts, in particular urea and
  • the pigments according to the invention are used in an amount of 0.05 to 30% by weight, preferably 0.1 to 15% by weight.
  • the pigments produced according to the invention are also suitable as colorants in electrophotographic toners and developers, such as, for example, one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, polymerization toners and special toners.
  • electrophotographic toners and developers such as, for example, one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, polymerization toners and special toners.
  • Typical toner binders are polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • the pigments prepared according to the invention are suitable as colorants in powders and powder coatings, in particular in triboelectrically or electrokinetically sprayable powder coatings which are used for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber ,
  • Epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are typically used as powder coating resins together with conventional hardeners. Combinations of resins are also used. For example, epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoles and dicyandiamide and their derivatives, blocked isocyanates, bisacyl urethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • the pigments according to the invention are suitable as colorants in ink-jet inks on an aqueous and non-aqueous basis and in inks which work according to the hot-melt process.
  • Ink-jet inks generally contain a total of 0.5 to 15% by weight, preferably 1.5 to 8% by weight (calculated on a dry basis) of one or more of the compounds prepared according to the invention.
  • Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator).
  • Microemulsion inks generally contain 0.5 to 15% by weight, preferably 1.5 to 8% by weight, of one or more of the compounds prepared according to the invention, 5 to 99% by weight of water and 0.5 to 94.5% by weight .-% organic solvent and / or hydrotropic compound.
  • "Solvent-based" ink jet inks preferably contain 0.5 to 15% by weight of one or more compounds produced according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds.
  • Hot-melt inks are usually based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx. 60 ° C and approx. 140 ° C.
  • Hot melt ink jet inks are e.g. essentially from 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the compounds prepared according to the invention. Furthermore, 0 to 20% by weight of an additional polymer (as a "dye dissolver"), 0 to 5% by weight of dispersing aid, 0 to
  • pigments produced according to the invention are also suitable as colorants for color filters both for additive and subtractive color production and for electronic inks.
  • PVC Soft polyvinyl chloride
  • a gravure printing system based on nitrocellulose (NC) was selected from the large number of known printing systems.
  • an alkyd-melamine resin lacquer (AM) based on a medium-oil alkyd resin and a butanol-etherified melamine resin was used from the large number of known lacquers High-solid acrylic stoving enamel based on a non-aqueous dispersion (HS) and an aqueous enamel based on polyurethane (PUR) selected.
  • the color strength and hue were determined in accordance with DIN 55986.
  • the rheology of the mill base after dispersion was assessed visually using the following five-point scale.
  • the fastness to overcoating was determined in accordance with DIN 53221.
  • the viscosity was determined after the millbase had been diluted to the final pigment concentration using the Rossmann viscose spatula, type 301 from Erichsen.
  • Gloss measurements were carried out on film infusions at an angle of 20 ° in accordance with DIN 67530 (ASTMD 523) using the "multigloss" gloss meter from Byk-Mallinckrodt.
  • Example 2 The chromophore from Example 2 was produced according to DE 24 51 097 Example 64. Comparison of example 2d) against comparison example 1
  • the lacquers in the AM lacquer of the pigment according to Example 2d) are significantly more intense, opaque and redder than those of Comparative Example 1.
  • the rheology is rated 3, the viscosity is 3.4 seconds, the gloss of a drawn paint has a value of 78 and the gloss of a cast paint has a value of 80.
  • the rheology is rated 1, the Viscosity cannot be measured (thickened too much), the paintwork is so matt that a gloss cannot be measured or cast.
  • the chromophore from Example 3 was prepared according to DE 24 51 097 Example 1 by using 5-aminobenzimidazolone as the base and 2-chloro-1,4-bis (acetoacetylamino) benzene as the coupling component.
  • the coatings in the AM coating of the pigment according to Example 3d) are significantly more intense and redder than those of Comparative Example 2.
  • the viscosity is 3.6 seconds, the gloss drawn has a value of 70 and the gloss cast has a value of 72.
  • the viscosity is 9.0 seconds, the gloss drawn has a value of only 32 and cast the varnish is so matt that a gloss can no longer be measured.
  • the coatings in the AM coating of the pigment according to Example 3e) are significantly more intense and redder and noticeably more opaque than those of Comparative Example 2.
  • the viscosity is 5.8 sec
  • the gloss drawn has a value of 71
  • the gloss cast has a value of 19.
  • Example 3 The chromophore from Example 5 was prepared according to DE 24 51 097 Example 1 by using 6-amino-7-methoxyquinoxaline-2,3-dione as the base and 2-chloro-1,4-bis (acetoacetylamino) benzene as the coupling component were. Comparison of example 5d) against comparison example 3
  • the lacquers in the AM lacquer of the pigment according to Example 5d) are significantly more intense and lighter in color, significantly more opaque, and also greener and purer than those of Comparative Example 3.
  • the viscosity is 3.8 seconds, the gloss drawn has a value of 69 and the gloss cast has a value of 69.
  • the viscosity is 4.3 seconds, the gloss drawn has a value of only 27 and Cast gloss has a value of only 15.
  • the coatings in the AM coating of the pigment according to Example 5e) are significantly more intense in color, significantly lighter, somewhat more opaque and, in addition, greener than those of Comparative Example 3.
  • the luster drawn has a value of 51 and the luster cast has a value of 38. In the case of Comparative Example 3, the luster drawn has a value of only 27 and the luster cast has a value of only 15.
  • the chromophore from Example 6 was prepared according to DE 24 51 097 Example 1 by using 6-amino-7-methoxyquinoxaline-2,3-dione as the base and
  • Coupling component 1 4-bis (acetoacetylamino) benzene were used.
  • the coatings in the AM coating of the pigment according to Comparative Example 4 are significantly weaker in color and redder and significantly more transparent than those in Example 6h.
  • the gloss drawn only has a value of 31 and the gloss cast has a value of only 22.
  • the paintwork of example 6h) is significantly more shiny: the gloss drawn has a value of 77 and the gloss cast has a value of 76.
  • the coatings in the AM coating of the pigment according to Comparative Example 4) are significantly weaker in color, more transparent and more yellow than those in Example 6i).
  • the gloss drawn has a value of only 31 and the gloss cast has a value of only 22.
  • the paintwork of example 6i) is significantly glossier: the gloss both drawn and cast has a value of 64.
  • the coatings in the AM coating of the pigment according to Comparative Example 4 are significantly weaker in color and significantly redder and significantly more transparent than those in Example 6k.
  • the gloss drawn has a value of only 31 and the gloss cast has a value of only 22.
  • the paintwork of example 6k) is significantly glossier: the gloss drawn has a value of 61 and the gloss cast has a value of 52.
  • Example 2d The pigments prepared according to Example 2d) and Comparative Example 5 were incorporated into a PVC plastic.
  • the colorations of Example 2d) are strong in color and have a pure, reddish-yellow hue.
  • the pigment from Comparative Example 5 is not dispersed, only black specks can be seen.
  • the PVC is not stained.
  • the pigment is completely unsuitable for coloring PVC. Both pigments were compared in an AM lacquer.
  • the pigment from comparative example 5 shows a dark, cloudy full tone and is significantly weaker in color than the pigment from example 2d), which provides a pure, light full tone.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention concerne un procédé pour produire des pigments disazoïques de formule générale (I) ou un mélange desdits pigments disazoïques par couplage azoïque. Dans la formule, R1 et R2 sont identiques ou différents et représentent hydrogène, alkyle C1-C4, alcoxy C1-C4, alcoxycarbonyle C1-C5, nitro, cyano, halogène, phénoxy ou trifluorométhyle; D1 et D2 sont identiques ou différents et représentent un hétérocycle aromatique sélectionné dans le groupe comprenant: benzimidazole, benzimidazolone, benzimidazole-thione, benzoxazole, benzoxazolone, benzothiazolone, indazole, phtalimide, naphtalimide, benzotriazole, quinoléine, benzodiazine, phénomorpholine, phénomorpholinone, benzo[c,d]indolone, benzimidazo[1,2-a]pyrimidone, carbazole et indole. L'invention est caractérisée en ce que les produits obtenus lors du couplage azoïque sont soumis à une finition dans un solvant organique présentant un pH alcalin ou dans un solvant organique aqueux présentant un pH neutre ou alcalin.
EP03735467A 2002-06-20 2003-05-27 Procede pour produire des pigments disazoiques Withdrawn EP1517962A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10227527 2002-06-20
DE10227527A DE10227527A1 (de) 2002-06-20 2002-06-20 Verfahren zur Herstellung von Disazopigmenten
PCT/EP2003/005520 WO2004000947A1 (fr) 2002-06-20 2003-05-27 Procede pour produire des pigments disazoiques

Publications (1)

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EP1517962A1 true EP1517962A1 (fr) 2005-03-30

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EP03735467A Withdrawn EP1517962A1 (fr) 2002-06-20 2003-05-27 Procede pour produire des pigments disazoiques

Country Status (6)

Country Link
US (1) US7262284B2 (fr)
EP (1) EP1517962A1 (fr)
JP (1) JP2005535738A (fr)
CN (1) CN1305971C (fr)
DE (1) DE10227527A1 (fr)
WO (1) WO2004000947A1 (fr)

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DE10353127A1 (de) * 2003-11-14 2005-06-09 Clariant Gmbh Pigmentzusammensetzungen aus gelbem Disazopigment und organischem Pigment
EP1834996B1 (fr) * 2006-03-14 2009-05-27 Clariant Finance (BVI) Limited Preparations pigmentaire a base de PY 155
US20100104966A1 (en) * 2007-01-25 2010-04-29 Ciba Corporation Crystal phase of a benzimidazolone azo pigment
DE102008006859A1 (de) 2008-01-31 2009-08-06 Clariant International Limited Verfahren zur Konditionierung von Carbonsäureestergruppen-haltigen Azopigmenten
US7563318B1 (en) 2008-07-02 2009-07-21 Xerox Corporation Method of making nanoscale particles of AZO pigments in a microreactor or micromixer
ES2547713T3 (es) * 2009-06-26 2015-10-08 Cardiac Pacemakers, Inc. Derivación de dispositivo médico que incluye una bobina unifilar con una capacidad de transmisión del par de torsión mejorada y un calentamiento por RM reducido
CN102482511B (zh) * 2009-09-04 2013-09-18 富士胶片株式会社 水性颜料分散体和喷墨记录用水性墨水
AU2010290459B2 (en) 2009-09-04 2014-06-12 Fujifilm Corporation Aqueous pigment dispersion, and aqueous ink for inkjet recording
EP2812445A2 (fr) 2012-02-10 2014-12-17 Novo Nordisk A/S Méthodes liées au traitement des maladies inflammatoires
WO2013169395A1 (fr) 2012-05-09 2013-11-14 Sun Chemical Corporation Particules de pigment modifiées en surface, leur procédé de préparation et leur application
CN103224715B (zh) * 2013-04-03 2014-07-23 中国中化股份有限公司 一种双乙酰乙酰对苯二胺类双偶氮化合物的制备方法
JP6894953B2 (ja) * 2014-11-04 2021-06-30 クラリアント・インターナシヨナル・リミテツド Ｃ．ｉ．ピグメントイエロー１５５とその製造方法、その顔料を用いた顔料組成物と着色剤組成物、及びそれらの着色剤としての使用
JP2016089020A (ja) * 2014-11-04 2016-05-23 クラリアント・インターナシヨナル・リミテツド Ｃ．ｉ．ピグメントイエロー１５５とその製造方法、その顔料を用いた顔料組成物と着色剤組成物、及びそれらの着色剤としての使用
CN104987747B (zh) * 2015-07-30 2017-03-15 沈阳化工研究院有限公司 一种苯并咪唑酮偶氮颜料及其制备与应用
CN105219119B (zh) * 2015-09-29 2017-03-08 陕西理工学院 一种噻唑酮并三苯胺类光敏染料及其制备方法
CN108690027B (zh) * 2018-06-15 2019-09-27 广州大学 一种2-二氟亚甲基取代嘧啶并[1,2-a]苯并咪唑化合物及其制备和应用

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Also Published As

Publication number Publication date
CN1305971C (zh) 2007-03-21
DE10227527A1 (de) 2004-01-08
US7262284B2 (en) 2007-08-28
JP2005535738A (ja) 2005-11-24
CN1662610A (zh) 2005-08-31
WO2004000947A1 (fr) 2003-12-31
US20060167236A1 (en) 2006-07-27

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