EP1476506A2 - Colorants azoiques jaunes hydrosolubles - Google Patents

Colorants azoiques jaunes hydrosolubles

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Publication number
EP1476506A2
EP1476506A2 EP03706416A EP03706416A EP1476506A2 EP 1476506 A2 EP1476506 A2 EP 1476506A2 EP 03706416 A EP03706416 A EP 03706416A EP 03706416 A EP03706416 A EP 03706416A EP 1476506 A2 EP1476506 A2 EP 1476506A2
Authority
EP
European Patent Office
Prior art keywords
formula
dye
substituted
hydroxy
sulfo
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Withdrawn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
EP03706416A
Other languages
German (de)
English (en)
Inventor
Andreas Wuzik
Josef Geisenberger
Heidemarie Menzel
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
Publication of EP1476506A2 publication Critical patent/EP1476506A2/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Withdrawn legal-status Critical Current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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
    • C09B29/33—Aceto- or benzoylacetylarylides
    • 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
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
    • C09B29/33—Aceto- or benzoylacetylarylides
    • C09B29/331—Aceto- or benzoylacetylarylides containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H2, OPO2H2; salts thereof
    • C09B29/332—Carbocyclic arylides
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/14—Monoazo compounds
    • C09B45/18—Monoazo compounds containing copper
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
    • C09B45/24—Disazo or polyazo compounds
    • C09B45/28—Disazo or polyazo compounds containing copper
    • 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
    • C09B45/00—Complex metal compounds of azo dyes
    • C09B45/48—Preparation from other complex metal compounds of azo dyes
    • 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
    • C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • C09D5/033—Powdery paints characterised by the additives
    • C09D5/035—Coloring agents, e.g. pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G9/00—Developers
    • G03G9/08—Developers with toner particles
    • G03G9/09—Colouring agents for toner particles
    • G03G9/0906—Organic dyes
    • G03G9/091—Azo dyes
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents

Definitions

  • the present invention describes new water-soluble yellow azo dyes, processes for their preparation and their use as recording liquids, in particular for the ink jet process (ink-jet printing).
  • the inkjet process is a non-contact printing process, generally distinguishing between two printing techniques: drop-on-demand and continuous stream.
  • the drop-on-demand principle is based on the fact that the ink in the form of a drop from a nozzle - electronically controlled - is placed in the right place at the right time, whereas with continuous stream printing the ink is permanently released and then, also after electronic charging either hits the recording medium (e.g. paper), or is distracted into a receptacle.
  • the recording liquids or the dyes contained therein must meet corresponding requirements, in particular with regard to lightfastness and waterfastness.
  • Lightfastness is particularly important for inkjet applications in outdoor areas and in the production of inkjet prints with photographic quality.
  • the present invention therefore relates to dyes of the general formula (2)
  • a and B are the same or different and for an optionally with 1, 2, 3 or 4 substituents from the group Ci-C ⁇ -alkyl, hydroxy, -C-C 6 - alkoxy, carboxy, sulfo, sulfonamide, amino and -C-C 6 -Alkylamino substituted C ⁇ -Cio-aryl radical; or for a 5- to 7-membered aromatic heterocycle which can be benzo-fused and can carry 1, 2, 3 or 4 of the abovementioned substituents, or in which A represents a radical of an azo dye of the formula (2a)
  • D 1 and D 2 are the same or different and for an optionally with 1, 2, 3 or 4 substituents from the group C C ⁇ -alkyl, hydroxy, Ci-C ⁇ -alkoxy, carboxy, sulfo, sulfonamide, amino and C- ⁇ -C 6 alkylamino substituted C 6 -C ⁇ o aryl;
  • Y represents an oxygen and / or nitrogen-containing group which optionally forms a 9- or 10-membered ring via X of the enolate function;
  • X is hydrogen, a monovalent metal cation, an equivalent of a polyvalent metal cation or an ammonium ion substituted with -CC 4 -alkyl, phenyl or (-C-C) alkoxy- (-C-C) -alkyl.
  • Preferred azo dyes of the formula (2) are those in which A and B are phenyl, naphthyl, pyridyl or pyrazolyl, those with 1 or 2 substituents from the group consisting of methyl, ethyl, propyl, hydroxy, methoxy, ethoxy, propoxy and carboxy , Sulfo, sulfonamido, amino and
  • Methylamino can be substituted.
  • Preferred azo dyes of the formula (2) are also those in which A is a radical of the formula (2a), in which D 1 and D 2 are phenyl or naphthyl, with 1 or 2 substituents from the group methyl, ethyl , Propyl, hydroxy, methoxy, ethoxy, propoxy, carboxy, sulfo, sulfonamido, amino and methylamino can be substituted.
  • Preferred azo dyes of the formula (2) are also those in which Y is hydroxy, methoxy, carboxy or amino.
  • Preferred azo dyes of the formula (2) are also those in which X is hydrogen, Na, K or a transition metal cation.
  • Particularly preferred azo dyes of the formula (2) are also those in which A and B are each phenyl or naphthyl radical substituted by 1 or 2 sulfo and / or carboxy groups.
  • Particularly preferred azo dyes of the formula (2) are also those in which A is a radical of the formula (2a), in which D 1 is a phenyl or naphthyl radical substituted by 1 or 2 sulfo groups, and D 2 is a radical by sulfo , Hydroxy or methoxy substituted phenyl radical.
  • Particularly preferred azo dyes of the formula (2) are also those in which X is Cu, Co, Ni, Fe or Cr, which together with Y forms a 9- or 10-membered ring.
  • X is Cu.
  • the present invention also relates to a process for the preparation of the dyes of the formula (2), characterized in that the amine of the formula (3)
  • reaction of (3) with (4) is preferably carried out at 0 to 40 ° C and pH 4 to 9.
  • the diazotization and coupling steps can be carried out by customary methods.
  • the diazotization is preferably carried out in aqueous solution or suspension
  • the azo coupling is preferably added in aqueous solution or suspension
  • the molar ratios between the respective diazonium salt and the respective coupling component are preferably 1: (0.8 to 2).
  • the complexation with a metal is conveniently done by adding an aqueous metal salt solution, e.g. a metal sulfate, chloride, bromide, hydrogen sulfate, bicarbonate or carbonate.
  • an aqueous metal salt solution e.g. a metal sulfate, chloride, bromide, hydrogen sulfate, bicarbonate or carbonate.
  • the complexation can be carried out in the acidic as well as in the basic range.
  • the temperature should be between 60 and 130 ° C, if necessary, heated under pressure.
  • the dyes of the invention can be isolated from the initially obtained, preferably aqueous, reaction mixtures by salting out, filtering or spray drying, if appropriate after partial or complete desalination by means of membrane filtration.
  • isolation can also be dispensed with and the reaction mixtures containing the dyes according to the invention by adding organic and / or inorganic bases and / or humectants and, if appropriate, in part or complete desalination can be transferred directly to concentrated dye solutions using membrane filtration.
  • the complex dyes can also be used as a press cake (optionally also in a flush process) or as a powder.
  • the dyes can be passed over an ion exchange resin in the form of their aqueous solutions.
  • the dyes according to the invention can additionally contain a shading dye, preferably from the group of the colorants listed in the Color Index, such as C.I. Acid Yellow 17 and 23, C.I. Direct Yellow 86, 98 and 132, C.I. Reactive Yellow 37, C.I. Pigment Yellow 17, 74, 83, 97, 120, 139, 151, 155 and 180; C.I. Direct Red 1, 11, 37, 62, 75, 81, 87, 89, 95, 227; C.I. Acid Red 1, 8, 80, 81, 82, 87, 94, 115, 131, 144, 152, 154, 186, 245, 249 and 289; C.I.
  • a shading dye preferably from the group of the colorants listed in the Color Index, such as C.I. Acid Yellow 17 and 23, C.I. Direct Yellow 86, 98 and 132, C.I. Reactive Yellow 37, C.I. Pigment Yellow 17, 74, 83, 97, 120, 139,
  • the shading colorant is preferably present in an amount of 0.001 to 5% by weight, in particular 0.01 to 1% by weight, based on the dry weight of the dye according to the invention.
  • the dyestuffs according to the invention can be mixed with the shading colorant by mixing the dyestuffs of the formula (2) and the shading colorant with one another in the stated mixing ratios in the form of dry powders, their solutions, water- or solvent-moist presscakes and / or masterbatches, or from the dyes manufactured inks nuanced.
  • the present invention also relates to the use of the (optionally nuanced) dyes of the formula (2) for dyeing and printing natural and synthetic fiber materials, such as polyester, silk, wool or blended fabrics, in particular for recording writing and images on various recording media, and for dyeing paper or pulp in bulk.
  • the dyes described are prepared in accordance with the requirements mentioned.
  • the dyes can be isolated from the initially obtained, preferably aqueous reaction mixtures by salting out and filtering or by spray drying, if appropriate after partial or complete desalination by means of membrane filtration and / or ion exchange.
  • isolation can also be dispensed with and the reaction mixtures containing dyes can be converted directly into concentrated dye solutions by adding organic and / or inorganic bases, possibly humectants, preservatives and, if appropriate, after partial or complete desalination by means of membrane filtration.
  • the dyes can also be used as a press cake (optionally also in a flush process) or as a powder.
  • the dyes according to the invention are used in as pure and salt-free form as possible, ie free of NaCl or other customary inorganic salts which have arisen in the synthesis of the dyes.
  • Inorganic bases suitable for concentrated dye solutions are, for example, lithium hydroxide, lithium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium carbonate, potassium hydroxide, potassium carbonate and ammonia.
  • Suitable organic bases are, for example, monoethanolamine, diethanolamine, triethanolamine, 2-aminopropanol, 3-aminopropanol, dipropanolamine, tripropanolamine, N-methylaminoethanol, N, N-dimethylamino ethanol, N-Phenylaminopropanol, ethylenediamine, tetramethylethylenediamine, tetramethylpropylenediamine, Tetramethylhexylendiamin, diethylenetriamine, triethylenetetramine , Triethylamine, diisopropylethylamine and polyethyleneimine.
  • Moisturizers suitable for concentrated dye solutions are, for example, formamide, urea, tetramethylurea, ⁇ -caprolactam, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, butyl glycol, methyl cellosolve, glycerol, N-methyl pyrrolidone, 1,3-diethyl-2-imidazolidin
  • the dyes according to the invention are particularly suitable for the production of recording liquids, in particular of aqueous and non-aqueous inks for the ink-jet printing process, and for inks which work according to the hot-melt process or are based on microemulsions, but also for other printing -, duplication, marking, writing, drawing, stamping or registration procedures.
  • the present invention also relates to recording liquids which contain a dye according to the invention and optionally other colorants for shading, as described above.
  • shading colorants are advantageously contained in an amount of 0 to 20% by weight, preferably 0.01 to 10% by weight, in particular 0.1 to 5% by weight, based on the total weight of the recording liquid.
  • the composition of the recording liquid must be adapted to the respective purpose.
  • Recording liquids according to the invention generally contain a total of 0.1 to 50% by weight of the dye of the formula (2) and optionally the shading colorant, calculated as dry weight, 0 to 99% by weight of water and 0.5 to 99.5% by weight. -% organic solvent and / or humectant.
  • the recording liquids contain 0.5 to 15% by weight of said dye, calculated as dry weight, 35 to 75% by weight of water and 10 to 50% by weight of organic solvent and / or humectant; in another preferred embodiment 0.5 to 15% by weight of said dye, calculated as dry weight, 0 to 20% by weight of water and 70 to 99.5% by weight of organic solvent and / or humectant.
  • Water is preferably used in the form of distilled or deionized water to prepare the dyes (2) and recording liquids containing them.
  • the solvents and / or humectants contained in the recording liquids can be an organic solvent or a mixture of such solvents, with water-miscible solvents are preferred.
  • Suitable solvents are, for example, monohydric or polyhydric alcohols, their ethers and esters, for example methanol, ethanol, propanol, isopropanol, butanol, isobutanol; di- or trihydric alcohols, in particular with 2 to 6 carbon atoms, for example ethylene glycol, propylene glycol, 1,3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 2,6- Hexanetriol, glycerin, diethylene glycol, dipropylene glycol, triethylene glycol, polyethylene glycol, tripropylene glycol, polypropylene glycol; lower alkyl ethers of polyhydric alcohols, such as, for example
  • the recording liquids according to the invention may also contain conventional additives, for example preservatives, cationic, anionic or nonionic surface-active substances (surfactants and wetting agents), and agents for regulating the viscosity, e.g. Polyvinyl alcohol, cellulose derivatives, or water-soluble natural or artificial resins as film formers or binders to increase the adhesive and abrasion resistance. It can also contain light stabilizers, optical brighteners, oxidizing agents, reducing agents and free radical scavengers.
  • Amines e.g. Ethanolamine, diethanolamine, triethanolamine, N, N-dimethylethanolamine, diisopropylamine, N-ethyldiisopropylamine to increase the pH of the recording liquid may be present, normally based on 0 to 10% by weight, preferably 0.5 to 5% by weight on the total weight of the recording liquid.
  • the recording liquids for the ink-jet printing process can also contain other additives, for example for buffering the pH , to adjust the electrical conductivity, the specific heat, the coefficient of thermal expansion and the conductivity.
  • the recording liquids according to the invention are in the ranges suitable for ink-jet processes. They deliver printed images of high optical density with excellent light and water fastness.
  • the dyes according to the invention can be used as an ink set in combination with magenta, cyan and black colorants.
  • the magenta, cyan and black tones are both dyes, such as the C.I. Dyes Reactive Red 23, C.I. Reactive Red 180, C.I. Acid Red 52, C.I. Acid Blue 9, C.I. Direct Blue 199, as well as pigments such as C.I. Pigment Red 122, C.I. Pigment Red 176, C.I. Pigment Red 184, C.I. Pigment Red 185 and C.I. Pigment Red 269, C.I. Pigment Violet 19, C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4. Black tones form the dyes C.I. Reactive Black 8, C.I. Reactive Black 31, C.I. Direct Black 168, C.I. Sol. Sulfur Black 1 and 2, C.I. Acid Black 194 and Russ.
  • the dye mixtures according to the invention are suitable as colorants in electrophotographic toners and developers, such as e.g. One-component and two-component powder toners, magnetic toners, liquid toners, polymerization toners and other special toners are suitable.
  • 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
  • the dye mixtures according to the invention are suitable as colorants in powders and powder coatings, in particular in triboelectrically or electrostatically sprayed 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 typically used are carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins together with conventional hardeners as powder coating resins. Combinations of resins are also used. For example, epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • the dyes according to the invention are suitable as colorants for color filters, both for additive and for subtractive color generation, and as colorants in electronic inks for so-called “electronic newspapers” and in the medical field.
  • the azo dyes according to the invention are also suitable as colorants in printing inks, lacquers, paints, plastics, rubber materials, office articles, wood paints and cleaning agents, artists' paints.
  • Typical printing inks are e.g. Offset printing inks, gravure inks and printing inks for water-based and solvent-based packaging printing and flexographic printing.
  • Typical paints are car series and refinish paints, industrial paints and architectural paints (e.g. plastic plasters or dispersion paints).
  • Typical plastic colors are e.g. those in hard and soft PVC (polyvinyl chloride), polyolefins or polystyrenes.
  • the dyes according to the invention can be used for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper and rubber.
  • the dyes according to the invention can additionally be shaded with the dyes and / or pigments listed above.
  • the light fastness is determined according to DIN 54003 (blue wool scale).
  • Example 1 Stage A: 0.06 mol of orthanilic acid are suspended in 200 ml of water and adjusted to pH 6 with 10 N sodium hydroxide solution. After stirring for 5 minutes at room temperature, the orthanilic acid has dissolved clearly. Then 0.18 mol of diketene is added dropwise within 10 min and the pH is kept at 5.5 to 6.0. The reaction is complete after about 1 hour.
  • Step B 0.06 mol of 3-amino-4-methoxy-benzenesulfonic acid is stirred into 150 ml of water in a separate vessel and the pH is adjusted to about 0.5 with 15 ml of 10N hydrochloric acid. After the solution has been stirred at 0 to 5 ° C. for 30 min, 0.066 mol of sodium nitrite is added and the mixture is stirred for 1 h. The excess nitrite is then removed with 0.75 g of amidosulfonic acid.
  • Stage C For the coupling, the intermediate product obtained in stage A is cooled to 10 ° C. and the pH is adjusted to 6. The diazonium salt solution prepared in stage B is added to this within 30 min and the pH is kept at 4.0-5.0 with 20 g of sodium acetate. The reaction is complete after 1 h and the dye (7) is obtained.
  • the coupler solution (step A) can be added to the diazo solution (step B).
  • the dye (7) can be added directly to an ink formulation or, as described in step D, reacted with a copper salt in order to further increase the light fastness.
  • Stage D The dye solution obtained from stage C is heated to 60 ° C. and mixed with a solution consisting of 0.066 mol of copper sulfate, ammonia and diethanolamine and heated to about 90 ° C. for about 1 to 2 hours.
  • the dye (8) is obtained in the form of an aqueous solution.
  • Example 2 Now, as in example 1 (stages A-C), you set
  • the dye solutions obtained from the examples are finely filtered through a depth filter (0.1-0.3 ⁇ m), passed over a cation exchanger and, after desalting, adjusted to color strength via a membrane desalination plant. It is then preserved with a biocide (e.g. ⁇ Proxel GXL).
  • a biocide e.g. ⁇ Proxel GXL
  • Example 4 Preparation of a recording liquid 2.5 g of pure dye according to Example 1 are desalted with stirring at 25 ° C. in a mixture of 20.0 g of diethylene glycol, 2.5 g of N-methylpyrrolidone, 1.0 g of triethanolamine and 76.5 g Water entered and dissolved.
  • EXAMPLE 5 Production of a Recording Liquid 2.5 g of pure dye according to Example 2 are stirred into a mixture of 20.0 g of diethylene glycol, 2.5 g of N-methylpyrrolidone, 1.0 g of triethanolamine and 1.0 g of urea while stirring at 25.degree and 75.5 g of demineralized water are added and dissolved.
  • EXAMPLE 6 Preparation of a Recording Liquid 2.5 g of pure dye according to Example 3 are introduced into a mixture of 20.0 g of diethylene glycol, 1.0 g of triethanolamine, 1.0 g of urea and 78.0 g of demineralized water with stirring at 25.degree and solved.
  • the inks produced in this way provide yellow printed images with very good lightfastness and storage stability.
  • the prepared recording liquids are stored at 60 ° C for 4 weeks to investigate the storage stability. No precipitations are observed after this time, the recording liquids can be finely filtered without residue. Colorimetric studies show no changes to the tests made before the storage stability tests.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Coloring (AREA)

Abstract

L'invention concerne des colorants correspondants à la formule (2), dans laquelle: A et B peuvent être identiques ou différents et représentent un reste aryle C6-C10 éventuellement substitué par 1, 2, 3 ou 4 substituants du groupe constitué par alkyle C1-C6, hydroxy, alcoxy C1-C6, carboxy, sulfo, sulfonamide, amino et alkyle C1-C6-amino, ou bien représentent un hétérocycle aromatique possédant 5 à 7 éléments, qui peut être benzoannelé et porter 1, 2, 3 ou 4 des substituants susmentionnés, ou bien A représente un reste d'un colorant azoïque correspondant à la formule (2a): D1-N=N-D2-, où D1 et D2 sont identiques ou différents et représentent un reste aryle C6-C10 substitué par 1, 2, 3 ou 4 substituants du groupe alkyle C1-C6, hydroxy, alcoxy C1-C6, carboxy, sulfo, sulfonamide, amino et alkyle C1-C6-amino; Y représente un groupe contenant de l'oxygène et/ou de l'azote qui constitue, éventuellement par l'intermédiaire du X de la fonction énolate, un cycle à 9 ou 10 éléments; et X représente hydrogène, un cation métal monovalent, un équivalent d'un cation métal polyvalent ou bien un ion ammonium substitué par alkyle C1-C4, phényle ou alcoxy (C1-C4)-alkyle (C1-C4).
EP03706416A 2002-02-13 2003-02-03 Colorants azoiques jaunes hydrosolubles Withdrawn EP1476506A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10205853A DE10205853A1 (de) 2002-02-13 2002-02-13 Wasserlösliche gelbe Azo-Farbstoffe
DE10205853 2002-02-13
PCT/EP2003/001021 WO2003068139A2 (fr) 2002-02-13 2003-02-03 Colorants azoiques jaunes hydrosolubles

Publications (1)

Publication Number Publication Date
EP1476506A2 true EP1476506A2 (fr) 2004-11-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP03706416A Withdrawn EP1476506A2 (fr) 2002-02-13 2003-02-03 Colorants azoiques jaunes hydrosolubles

Country Status (9)

Country Link
US (1) US7297200B2 (fr)
EP (1) EP1476506A2 (fr)
JP (1) JP2006503928A (fr)
KR (1) KR20040089618A (fr)
CN (1) CN1643076A (fr)
BR (1) BR0307676A (fr)
CA (1) CA2475624A1 (fr)
DE (1) DE10205853A1 (fr)
WO (1) WO2003068139A2 (fr)

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DE102007008218A1 (de) * 2007-02-20 2008-08-21 Clariant International Ltd. Pigmentzusammensetzung auf Basis von C.I. Pigment Yellow 191
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WO2003068139A2 (fr) 2003-08-21
WO2003068139A3 (fr) 2004-05-21
CA2475624A1 (fr) 2003-08-21
BR0307676A (pt) 2005-06-07
KR20040089618A (ko) 2004-10-21
US7297200B2 (en) 2007-11-20
DE10205853A1 (de) 2003-08-21
CN1643076A (zh) 2005-07-20
US20050090654A1 (en) 2005-04-28
JP2006503928A (ja) 2006-02-02

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