WO1997047690A1 - Dye mixtures - Google Patents

Dye mixtures Download PDF

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Publication number
WO1997047690A1
WO1997047690A1 PCT/EP1997/002817 EP9702817W WO9747690A1 WO 1997047690 A1 WO1997047690 A1 WO 1997047690A1 EP 9702817 W EP9702817 W EP 9702817W WO 9747690 A1 WO9747690 A1 WO 9747690A1
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Prior art keywords
formula
optionally substituted
alkyl
dye
dyes
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PCT/EP1997/002817
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German (de)
French (fr)
Inventor
Gunther Lamm
Andreas Johann Schmidt
Rüdiger Sens
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Basf Aktiengesellschaft
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Publication of WO1997047690A1 publication Critical patent/WO1997047690A1/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3858—Mixtures of dyes, at least one being a dye classifiable in one of groups B41M5/385 - B41M5/39
    • 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
    • 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
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • D06P1/20—Anthraquinone dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/003—Transfer printing
    • D06P5/004—Transfer printing using subliming dyes
    • D06P5/006—Transfer printing using subliming dyes using specified dyes

Definitions

  • the present invention relates to novel dye mixtures containing at least one pyridone dye of the formula I,
  • X 1 is a 5- or 6-membered carbocyclic or heterocyclic radical
  • Ci-C 13 alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, optionally substituted phenyl or a radical of the formula NE X E 2 , where E 1 and E 2 are each independently of one another hydrogen, C1-C13-alkyl, which is optionally substituted and may be interrupted by 1 to 3 oxygen atoms in ether function, C 5 C 7 cycloalkyl, optionally substituted phenyl, optionally substi ⁇ tutechnischs pyridyl, optionally substituted C ⁇ -C ⁇ 3 -Alka- noyl, C ⁇ -C ⁇ 3 alkoxycarbonyl, optionally substituted C ⁇ -C ⁇ 3 alkylsulfonyl, C 5 -C 7 cycloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally substituted pyridylsulfonyl, optionally substituted benzoyl,
  • R ⁇ R 2 and R 3 are each independently hydrogen
  • C 1 -C 1 3 -alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, substituted phenyl or optionally substituted C 3 -C 7 -cycloalkyl,
  • R 5 cyano, carbamoyl ,. Ci-C 6 alkoxycarbonyl, carboxyl or -CC 4 alkanoyl and
  • L 1 is hydrogen, C 1 -C 0 -alkyl or optionally substituted phenyl,
  • L 2 and L 3 are each independently hydrogen
  • G 2 wherein G 1 represents oxygen or sulfur and G 2 represents hydrogen or Ci-C ⁇ -monoalkylsulfamoyl, the alkyl chain of which can be interrupted by 1 or 2 oxygen atoms in ether function, and
  • L 4 denotes amino, hydroxyl or Ci-Cio-alkylthio optionally substituted by phenyl,
  • the object of the present invention was therefore to provide new dye mixtures which are advantageously suitable for thermal transfer.
  • Residues D can e.g. derive from a diazo component originating from the aniline, phenylazoaniline, aminothiophene, phenylazo aminothiophene, aminothiazole, phenylazoaminothiazole, aminoisothiazole or aminothiadiazole series.
  • dye mixtures which contain at least one azo dye of the formula II in which the radical D is, for example, a diazo component D-NH 2 of the formula
  • R 6 , R 7 and R 8 are each independently hydrogen
  • C 1 -C 13 alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, cyano, halogen, nitro or a radical of the formula -CO-OR 16 , -CO-NR 16 R 17 , -S0 2 -R 16 , -S0 2 -OR 16 , S0 2 -NR 16 Ri 7 or
  • R 16 and R 17 each independently represent hydrogen, C 1 -C 13 -alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function,
  • R 9 is hydrogen, chlorine, cyano, -C 8 alkyl, which can be interrupted by 1 oxygen atom in ether function, -C 8 alkoxy, -C 8 alkylthio, optionally substituted phenyl, benzyl, benzyloxy or one Rest of the formula -CO-OR 16 or -CO-NR 16 R 17 , in which R 16 and R 17 each have the abovementioned meaning,
  • R 10 is hydrogen, cyano, nitro or a radical of the formula -CO-OR 16 or -CO-NR 16 R 17 , wherein R 16 and R 17 are each the above
  • R 11 cyano, nitro, formyl or a radical of the formula
  • R 12 and R 13 are each independently hydrogen
  • R 14 is hydrogen, -C 4 alkyl or chlorine
  • R 15 is cyano or a radical of the formula -CO-OR 16 or -CO-NR 16 R 17 , in which R 16 and R 17 each have the abovementioned meaning.
  • X 1 represents a 5- or 6-membered carbocyclic or heterocyclic, preferably aromatic, radical which is optionally substituted and can be benzo-fused.
  • Residues X 1 can be derived, for example, from components from the benzene, indole, quinoline, naphthalene, pyrrole, thiazole, benzimidazole, benzothiazole, aminothiophene or pyridine series.
  • Important radicals X 1 are, for example, those of the formulas Va to Vj
  • n 0 or 1
  • Z 1 for hydrogen, -CC 3 -alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function, hydroxy, C ! -C 4 -alkoxy, -CC 4 -alkylsulfonylamino, -CC 4 -mono- or dialkylaminosulfonylamino or the rest -NHCOZ 7 or -NHCO 2 Z 7 , where Z 7 has the meaning of phenyl, benzyl, tolyl or C 1 -C 13 - alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function, Z 2 for hydrogen, -C 4 alkyl or -C 4 alkoxy,
  • Z 3 and Z 4 are each independently of one another hydrogen, C 1 -C 13 -alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, C 3 -C 4 -alkenyl, C 5 -C 7 -cycloalkyl , Phenyl or tolyl or together with the nitrogen atom connecting them for a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms,
  • Z 6 for hydrogen, halogen, C 1 -C 3 -alkyl, optionally substituted phenyl, optionally substituted benzyl, C 5 -C 7 cycloalkyl, thienyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl- thio or -CC 3 -monoalkylamino.
  • alkyl radicals occur in the abovementioned formulas, unless otherwise noted, substituents such as cyclohexyl, optionally substituted phenyl, Ci-C ⁇ -alkanoyloxy, Ci-C ⁇ -alkylaminocarbonyloxy, Ci-C ß -alkoxycarbonyl can be used as substituents , Ci-C ß -alkoxycarbonyloxy, where the alkyl chain of the latter two radicals is optionally interrupted by 1 to 3 oxygen atoms in ether function and can be substituted by phenyl or phenoxy, cyclohexyloxy, phenoxy, halogen, hydroxy or cyano.
  • the alkyl radicals generally have 1 or 2 substituents.
  • alkyl radicals which are interrupted by oxygen atoms in ether function occur in the formulas mentioned above, preference is given to those alkyl radicals which are interrupted by 1 or 2 oxygen atoms in ether function.
  • substituted cyclohexyl, phenyl or pyridyl radicals occur in the abovementioned formulas, then substituents, for example C 1 -C 8 -alkyl, C 1 -C 8 alkoxy, benzyloxy, halogen, in particular chlorine or bromine, nitro or carboxyl, can be used be considered.
  • the cyclohexyl, phenyl or pyridyl radicals generally have 1 to 3 substituents.
  • alkyl radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, see-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl , Isononyl, decyl, isodecyl undecyl, dodecyl, tri- decyl, isotridecyl (the names isooctyl, isononyl, iso-decyl and isotridecyl are trivial names derived from those obtained by the oxo process alcohols -.
  • Alkenyl radicals are, for example, prop-1-en-3-yl, but-2-en-4-yl or 2-methylprop-l-en-3-yl.
  • Cycloalkyl radicals are, for example, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl or cycloheptyl.
  • Phenyl radicals are e.g. Phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4 -1sopropylphenyl, 2-, 3- or 4- Butylphenyl, 2,3-, 2,4- or 2, 6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4- or 2, 6-Dirnethoxypheny1, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl or 2-, 3- or 4-nitrophenyl or 2-, 3rd - or 4-carboxylphenyl.
  • Pyridyl residues are e.g. Pyridyl, 2-, 3- or 4-methylpyridyl or 2-, 3- or 4-carboxylpyridyl.
  • Carbamoyl residues are e.g. Mono- or dimethylcarbamoyl, mono- or diethylcarbamoyl, mono- or dipropylcarbamoyl, mono- or diisopropylcarbamoyl, or mono- or dibutylcarbamoyl.
  • Alkylthio residues are e.g. Methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, heptylthio, octylthio, isooctylthio, 2-ethylhexylthio, nonylthio, isononylthio, decylthio or isodecylthio.
  • Alkoxy residues are e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, isooctyloxy or 2-ethylhexyloxy.
  • Halogen is e.g. Fluorine, chlorine or bromine.
  • Alkylsulfonyl, cycloalkylsufonyl, phenylsulfonyl and pyridylsulfonyl radicals are e.g. Methylsulfonyl, ethylsulfonyl, propyl sulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, pentylsulfonyl, Isopentylsulfonyl, neopentyl sulfonyl, hexylsulfonyl, Heptylsulfonyl, octylsulfonyl, 2-Ethyl ⁇ hexylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl,
  • Alkoxycarbonyl radicals are, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, hexyloxycarbonyl, heptyloxy- carbonyl, octyloxycarbonyl, isooctyloxycarbonyl or 2-ethylhexyloxycarbonyl.
  • Alkanoyl and benzoyl residues are e.g. Formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, benzoyl, 2-, 3- or 4-methylbenzoyl, 2-, 3- or 4-methoxybenzoyl, 2-, 3- or 4-chlorobenzoyl or 2-, 3rd - or 4-nitrobenzoyl.
  • Alkylsulfonylamino and mono- or dialkylamino sulfonylamino residues are e.g. Methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino, mono- or dimethylaminosulfonylamino, mono- or diethylaminosulfonylamino, mono- or dipropylaminosulfonylamino, mono- or diisopropylamino-sulfonylamino-nylamosulfonylamino-nylamino-naphonamino-nylamino-naphonamino- amino.
  • Alkoxy residues are e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, 2-ethylhexyloxy, nonyloxy, isononyloxy, Decyloxy, isodecyloxy, 2-, 3- or 4-methylbenzyloxy, 2- (2-, 3- or 4-methylphenyl) ethoxy.
  • Sulfamoyl residues are e.g. Methylsulfamoyl, ethylsulfamoyl, propylsulfamoyl, isopropylsulfamoyl, butylsulfamoyl, pentylsulfamoyl, hexylsulfamoyl, heptylsulfamoyl, octylsulfamoyl, 2-ethylhexylsulfamoyl, 2-methoxyethylsulfamoyloxamoyl, 3-ethoxysulfamoyl, 3-ethoxysulfamoyl, or 3,6-dioxaheptylsulfamoyl or 2-ethoxyethylsulfamoyl, 3, 6-dioxaoctylsulfamoyl.
  • radicals E 1 and E 2 or Z 3 and Z 4 together with the nitrogen atom connecting them, each represent a 5- or 6-membered saturated heterocyclic radical which optionally contains further hetero atoms, for example pyrrolidinyl,
  • Preferred mixture partners are pyridone dyes of the formula I in which X 2 is cyano.
  • Preferred mixture partners are furthermore pyridone dyes of the formula I in which X 3 is C 1 -C 13 -alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function.
  • Particularly preferred mixture partners are pyridone dyes of the formula I in which X 3 denotes Ci-C ß- alkyl, which is optionally interrupted by 1 or 2 oxygen atoms in ether function.
  • pyridone dyes of the formula I in which X 1 is a radical which is derived from a component from the thiazole or indole series, in particular a radical of the formula Vi or Vj.
  • mixing partners are pyridone dyes of the formula la
  • Z 3 and Z 4 are each independently of one another C 1 -C 8 -alkyl, which is optionally substituted by C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or phenyl, cyclopentyl, cyclohexyl or prop-l-en-3-yl and
  • Z 6 is branched C 3 -C 10 alkyl or phenyl, in particular branched C 3 -C 8 alkyl.
  • mixing partners are pyridone dyes of the formula Ia in which Z 6 is branched C 3 -C 6 -alkyl, in particular branched C 5 -alkyl, neopentyl being particularly mentioned.
  • pyridone dyes of the formula Ia in which, when the Z 3 and Z 4 radicals are each C 1 -C 8 -alkyl, the sum of the carbon atoms present in the two Z 3 and Z 4 radicals is at least 7, in particular is at least 8. Also particularly noteworthy as mixing partners are pyridone dyes from Foremi lb
  • X 3 and Z 3 each independently represent C 1 -C 8 -alkyl.
  • Preferred mixture partners are azo dyes of the formula II in which R 4 is methyl and R 1 , R 2 and R 3 are each, independently of one another, hydrogen or C 1 -C 13 -alkyl which is optionally substituted by hydroxy, acetyloxy, cyano or phenyl and by 1 up to 3 oxygen atoms can be interrupted in ether function.
  • Particularly interesting mixture partners are azo dyes of the formula II, in which the radical D is derived from a diazo component which obeys the formula IVa, IVb, IVc, IVd, IVe, IVf or IVg.
  • R 9 is hydrogen, chlorine, -CC 8 alkyl, optionally by C ! -C 4 alkyl or -C ⁇ C4-alkoxy substituted phenyl or benzyl, R 10 cyano or a radical of the formula -CO-OR 18 or -CO-NR 18 R 19 , wherein R 18 and R 19 each have the abovementioned meaning and
  • R 11 is a radical of the formula
  • R 9 is hydrogen, chlorine, C ⁇ -C8 alkyl, optionally substituted by C ⁇ -C 4 alkyl or C 1 -C 4 -alkoxy-substituted phenyl or benzyl and
  • R 11 is cyano, nitro, formyl or a radical of the formula -CO-OR 18 , where R 18 has the meaning given above.
  • Ci-C ß- alkyl which can be interrupted by 1 oxygen atom in ether function, Ci-C ⁇ -alkoxy, optionally substituted by C ⁇ -C 4 alkyl or C ⁇ -C 4 alkoxy phenyl, benzyl or benzyloxy and
  • R 10 is cyano, nitro or the rest of the formula -CO-OR 18 , where R 18 has the abovementioned meaning.
  • Particularly preferred mixture partners are azo dyes of the formula II, in which the radical D is derived from a diazo component which obeys the formula IVc, where
  • R 9 is hydrogen, chlorine, C 1 -C 8 -alkyl, which can be interrupted by 1 oxygen atom in ether function, C 1 -C 8 -alkoxy, phenyl optionally substituted by C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, Benzyl or the rest of the formula -CO-OR 18 , where R 18 has the meaning given above, R 10 cyano or the rest of the formula -CO-OR 18 , where R 18 has the meaning given above and
  • R 11 is cyano, nitro, formyl or the radical of the formula -CO-OR 18 , where R 18 has the meaning given above.
  • Preferred mixture partners are anthraquinone dyes of the formula III in which L 1 is hydrogen and L 4 is hydroxy and L 2 and L 3 each have the abovementioned meaning.
  • Preferred mixture partners are also anthraquinone dyes of the formula III, in which L 2 and / or L 3 is a radical of the formula
  • Preferred mixture partners are also anthraquinone dyes of the formula purple
  • the dye mixtures according to the invention generally contain 35 to 80% by weight, preferably 30 to 70% by weight and in particular 40 to 60% by weight, in each case based on the weight of the dye mixture, one or more pyridone dyes of the formula I and 20 up to 80% by weight, preferably 30 to 70% by weight and in particular 40 to 60% by weight, in each case based on the weight of the dye mixture, one or more azo dyes of the formula II and / or anthraquinone dyes of the formula III.
  • the new dye mixtures can be obtained by methods known per se, for example by mixing the individual dyes in the weight ratio mentioned above.
  • the pyridone dyes of the formula I are known and are described, for example, in WO-A-96/15195 and in German patent application 196 48 564.9.
  • the azo dyes of formula II are also known per se and e.g. in US-A-4 939 118 or US-A-5 403 363 or can be obtained by the methods mentioned therein.
  • the anthraquinone dyes of the formula III are also known per se and are described, for example, in K. Venkataraman "The Chemistry of Synthetic Dyes", Vol. III, pages 391 to 413, Academic Press, New York, London, 1970.
  • the dye mixtures according to the invention are distinguished by advantageous performance properties. They have high solubility in the ink ribbon (good compatibility with the binder), high stability in the printing ink, good transferability, high image stability (ie good light fastness and good stability against environmental influences, for example moisture, temperature or chemicals) and ensure flexible coloristic adaptation to the remaining subtractive primary colors, resulting in high-quality color spaces.
  • the spectrally uniform decrease in the individual components when irradiated i.e. the individual dye with the lower light fastness generally does not preferably decrease.
  • the dye mixtures according to the invention produce prints or dyeings which are very brilliant, strong in color and stable.
  • Another object of the present invention is a method for transferring dyes from a support to a plastic-coated paper by diffusion or sublimation with the aid of an energy source, which is characterized in that a support is used on which a dye mixture specified at the beginning.
  • the dye mixtures are processed into a printing ink in a suitable organic solvent or in mixtures of solvents with one or more binders, if appropriate with the addition of auxiliaries.
  • a suitable organic solvent or in mixtures of solvents with one or more binders if appropriate with the addition of auxiliaries.
  • the printing ink can be applied to the inert carrier by means of a squeegee and the coloring in air be dried.
  • Suitable organic solvents for the dye mixtures are, for example, those in which the solubility of the dye mixtures at a temperature of 20 ° C. is greater than 1% by weight, preferably greater than 5% by weight.
  • Examples include ethanol, propanol, isobutanol, tetrahydrofuran, methylene chloride, methyl ethyl ketone, cyclopentanone, cyclohexanone, toluene, chlorobenzene or mixtures thereof.
  • Suitable binders are all resins or polymer materials which are soluble in organic solvents and which are able to bind the dye mixtures to the inert support in an abrasion-resistant manner. Preference is given to binders which, after the printing ink has dried in air, absorb the dye mixture in the form of a clear, transparent film without any visible crystallization of the dye mixture.
  • Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyral, polyvinyl acetate, cellulose propionate or saturated linear polyesters.
  • the weight ratio of binder: dye mixture is generally 1: 1 to 10: 1.
  • Suitable inert carriers are e.g. in US-A-5 132 438 or in the corresponding patent applications cited therein.
  • the thickness of the carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
  • all temperature-stable plastic layers with an affinity for the dyes to be transferred are suitable as the dye receiver layer. Further details can be found, for example, in US Pat. No. 5,132,438 or the corresponding patent applications cited therein.
  • the transfer takes place by means of an energy source, for example by means of a laser or a thermal head, the latter having to be able to be heated to a temperature of> 300 ° C. so that the dye transfer can take place in the time range t: 0 ⁇ t ⁇ 15 msec.
  • the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
  • the dye mixtures according to the invention are furthermore advantageously suitable for dyeing or printing synthetic materials, e.g. of polyesters, polyamides or polycarbonates.
  • synthetic materials e.g. of polyesters, polyamides or polycarbonates.
  • textile materials such as fibers, yarns, twists, knitwear, woven goods or non-wovens made of polyester, modified polyester, e.g. anionically modified polyester, or blended fabrics of polyester with cellulose, cotton, viscose or wool.
  • the dyeing and printing conditions which also include dyeing in supercritical carbon dioxide, are known per se.
  • the new dye mixtures are also advantageously suitable for printing on materials using the ink jet process.
  • Suitable substrates are in addition to the above, e.g. Paper, glass, ceramics, plastics or metals.
  • the dyes according to the invention can also be used to dye ceramic fibers, e.g. in hair dyeing or dyeing furs.
  • the new dye mixtures are furthermore advantageously suitable for the production of color filters, such as those e.g. are described in EP-A-399 473.
  • the mixture is knife-coated with a 10 ⁇ m doctor blade onto a 6 ⁇ m thick polyester film, on the back of which a suitable sliding layer is applied, and blown dry with a hair dryer for 1 minute. Before the ribbon can be printed, it must be left to air dry for at least 24 hours, as residual solvents can impair the printing process.
  • the ink ribbons are printed onto commercially available video print paper (color video print paper from Hitachi) on a computer-controlled test arrangement which is equipped with a commercially available thermal head.
  • the energy output of the thermal head is controlled by changing the voltage, the set pulse duration being 7 ms and only one pulse being output at a time.
  • the energy delivered is between 0.5 and 2.0 mJ / dot.
  • the value for the assessment of the light fastness is the number of irradiation hours after which 20% of the amount of dye originally present had been destroyed.
  • 10 g of polyester fabric are placed at a temperature of 50 ° C. in 200 ml of a dyeing liquor which contains X% by weight, based on the polyester fabric, of the dye mixture and whose pH is adjusted to 4.5 using acetic acid. It is treated for 5 minutes at 50 ° C., then the temperature of the liquor is raised to 130 ° C. within 30 minutes, kept at this temperature for 60 minutes and then allowed to cool to 60 ° C. within 20 minutes.
  • the dyed-out polyester fabric is then reductively cleaned by placing it in 200 ml of a liquor containing 5 ml / l 32 wt. -% sodium hydroxide solution, 3 g / 1 sodium dithionite and 1 g / 1 of an adduct of 48 mol of ethylene oxide with 1 mol of Ricinusol, treated at 65 ° C. Finally, the tissue is rinsed, neutralized with dilute acetic acid, rinsed again and dried.
  • Dye mixtures Nos. 41, 42 and 43 were each used in an amount (X) of 0.35% by weight. Highly brilliant red dyeings with excellent lightfastness were obtained.
  • Dyes Nos. 22 and 28 were further mixed in a mass ratio of 1: 1, 1: 2 and 1: 3, and the mixtures were each used in an amount (X) of 0.35% by weight. Highly brilliant dyeings with excellent lightfastness were also obtained.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
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  • Plural Heterocyclic Compounds (AREA)

Abstract

Dye mixtures containing one or more azo dyes with a coupling component from the diaminopyridine series and one or more methine dyes from the trifluoromethyl pyridone series class, a process for the thermal transfer of said dye mixtures and a process for dyeing or printing synthetic materials by means of said dye mixtures.

Description

FarbstoffmischungenDye mixtures
Beschreibungdescription
Die vorliegende Erfindung betriff- neue Farbstoffmischungen, enthaltend mindestens einen Pyridonfarbstoff der Formel I,The present invention relates to novel dye mixtures containing at least one pyridone dye of the formula I,
Figure imgf000003_0001
Figure imgf000003_0001
in derin the
X1 einen 5- oder 6-gliedrigen carbocyclischen oder hetero- cyclischen Rest,X 1 is a 5- or 6-membered carbocyclic or heterocyclic radical,
X2 Cyano, Carbamoyl, Ci-Cβ-Alkoxycarbonyl, Carboxyl oderX 2 cyano, carbamoyl, Ci-Cβ-alkoxycarbonyl, carboxyl or
Ci-C4-Alkanoyl undCi-C 4 alkanoyl and
X3 Ci-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, gegebenenfalls substituiertes Phenyl oder einen Rest der Formel NEXE2, wobei E1 und E2 unabhängig voneinander jeweils für Wasserstoff, C1-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, C5-C7-Cycloalkyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substi¬ tuiertes Pyridyl, gegebenenfalls substituiertes Cι-Cχ3-Alka- noyl, Cι-Cι3-Alkoxycarbonyl, gegebenenfalls substituiertes Cι-Cι3-Alkylsulfonyl, C5-C7-Cycloalkylsulfonyl, gegebenenfalls substituiertes Phenylsulfonyl, gegebenenfalls substituiertes Pyridylsulfonyl, gegebenenfalls substituiertes Benzoyl, Pyridylcarbonyl oder Thienylcarbonyl oder E1 und E2 zusammen mit dem sie verbindenden Stickstoffatom gegebenenfalls durch Cι-C-4-Alkyl substituiertes Succinimido, gegebenenfalls durch Cι-C4-Alkyl substituiertes Phthalimido oder einen 5- oder 6-gliedrigen gesättigten heterocyclischen Rest, der gegebenenfalls weitere Heteroatome enthält, stehen, bedeuten, sowie mindestens einen Azofarbstoff der Formel IIX 3 Ci-C 13 alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, optionally substituted phenyl or a radical of the formula NE X E 2 , where E 1 and E 2 are each independently of one another hydrogen, C1-C13-alkyl, which is optionally substituted and may be interrupted by 1 to 3 oxygen atoms in ether function, C 5 C 7 cycloalkyl, optionally substituted phenyl, optionally substi¬ tuiertes pyridyl, optionally substituted Cι-Cχ 3 -Alka- noyl, Cι-Cι 3 alkoxycarbonyl, optionally substituted Cι-Cι 3 alkylsulfonyl, C 5 -C 7 cycloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally substituted pyridylsulfonyl, optionally substituted benzoyl, pyridylcarbonyl or thienylcarbonyl or E 1 and E 2 together with the one connecting them Succinimido optionally substituted by C 4 -C 4 alkyl, optionally by C 4 -C 4 alkyl are substituted phthalimido or a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms, and at least one azo dye of the formula II
Figure imgf000004_0001
Figure imgf000004_0001
in derin the
R^R2 und R3 unabhängig voneinander jeweils Wasserstoff,R ^ R 2 and R 3 are each independently hydrogen,
C1-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, substituiertes Phenyl oder gegebenenfalls substi¬ tuiertes C3-C7-Cycloalkyl,C 1 -C 1 3 -alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, substituted phenyl or optionally substituted C 3 -C 7 -cycloalkyl,
R4 Cι-C4-Alkyl,R 4 -CC 4 alkyl,
R5 Cyano, Carbamoyl,. Ci-C6-Alkoxycarbonyl, Carboxyl oder Cι-C4-Alkanoyl undR 5 cyano, carbamoyl ,. Ci-C 6 alkoxycarbonyl, carboxyl or -CC 4 alkanoyl and
D den Rest einer Diazokomponente bedeuten,D represents the remainder of a diazo component,
und/oder einen Anthrachinonfarbstoff der Formel IIIand / or an anthraquinone dye of the formula III
Figure imgf000004_0002
Figure imgf000004_0002
in derin the
L1 Wasserstoff, Cι-Cι0-Alkyl oder gegebenenfalls substituiertes Phenyl,L 1 is hydrogen, C 1 -C 0 -alkyl or optionally substituted phenyl,
L2 und L3 unabhängig voneinander jeweils Wasserstoff,L 2 and L 3 are each independently hydrogen,
Cι-Cιrj-Alkoxy, Benzyloxy, C1-C4-Alkylbenzyloxy, 2-Phenyl ethoxy, 2- (Cι-C4-Alkylphenyl)ethoxy, C1-C10-Alkylthio, Benzylthio, 2-Phenylethylthio, Halogen, Hydroxyphenyl, Cι-C4-Alkoxyphenyl oder einen Rest der FormelCι-Cιrj-alkoxy, benzyloxy, C 1 -C 4 alkylbenzyloxy, 2-phenyl ethoxy, 2- (Cι-C 4 alkylphenyl) ethoxy, C 1 -C 10 alkylthio, benzylthio, 2-phenylethylthio, halogen, hydroxyphenyl, C 1 -C 4 alkoxyphenyl or a radical of the formula
G2
Figure imgf000004_0003
worin G1 für Sauerstoff oder Schwefel und G2 für Wasserstoff oder Ci-Cβ-Monoalkylsulfamoyl, dessen Alkylkette durch 1 oder 2 Sauerstoffatome in Etherfunktion unterbrochen sein kann, stehen, undG 2
Figure imgf000004_0003
wherein G 1 represents oxygen or sulfur and G 2 represents hydrogen or Ci-Cβ-monoalkylsulfamoyl, the alkyl chain of which can be interrupted by 1 or 2 oxygen atoms in ether function, and
L4 Amino, Hydroxy oder gegebenenfalls durch Phenyl substituier¬ tes Ci-Cio-Alkylthio bedeuten,L 4 denotes amino, hydroxyl or Ci-Cio-alkylthio optionally substituted by phenyl,
ein Verfahren zu ihrer thermischen Übertragung sowie ein Ver- fahren zum Färben oder Bedrucken von synthetischen Materialien mittels der neuen Färbstoffmischungen.a process for their thermal transfer and a process for dyeing or printing synthetic materials using the new dye mixtures.
Es ist bekannt, das Thermotransferdruckverfahren mit einzelnen Farbstoffen oder auch mit Mischungen von Farbstoffen durchzu- führen. Dabei hat sich jedoch gezeigt, daß die zur Anwendung kommenden Farbstoffe noch anwendungstechnische Mängel aufweisen.It is known to carry out the thermal transfer printing process with individual dyes or with mixtures of dyes. It has been shown, however, that the dyes used still have application defects.
Aufgabe der vorliegenden Erfindung war es daher, neue Farbstoff- mischungen bereitzustellen, die sich in vorteilhafter Weise zur thermischen Übertragung eignen.The object of the present invention was therefore to provide new dye mixtures which are advantageously suitable for thermal transfer.
Demgemäß wurden die eingangs näher bezeichneten Farbstoff- mischungen gefunden.We have found that this object is achieved by the dye mixtures specified at the outset.
Reste D können sich z.B. von einer Diazokomponente ableiten, die aus der Anilin-, Phenylazoanilin-, Aminothiophen-, Phenylazo- aminothiophen-, Aminothiazol-, Phenylazoaminothiazol-, Aminoiso- thiazol- oder Aminothiadiazolreihe stammt.Residues D can e.g. derive from a diazo component originating from the aniline, phenylazoaniline, aminothiophene, phenylazo aminothiophene, aminothiazole, phenylazoaminothiazole, aminoisothiazole or aminothiadiazole series.
Hervorzuheben sind Färbstoffmischungen, die mindestens einen Azo- farbstoff der Formel II enthalten, in der sich der Rest D z.B. von einer Diazokomponente D-NH2 der FormelTo be emphasized are dye mixtures which contain at least one azo dye of the formula II in which the radical D is, for example, a diazo component D-NH 2 of the formula
ψ o < y
Figure imgf000005_0001
 ψ o <y
Figure imgf000005_0001
(IVa) (IVb) © (IVa) (IVb) ©
Figure imgf000006_0001
Figure imgf000006_0001
Figure imgf000006_0002
Figure imgf000006_0002
(IVh)(IVh)
ablei tet , wobeiderived, whereby
R6, R7 und R8 unabhängig voneinander jeweils Wasserstoff,R 6 , R 7 and R 8 are each independently hydrogen,
C1-C13-Alkyl, das gebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, Cyano, Halogen, Nitro oder einen Rest der Formel -CO-OR16, -CO-NR16R17, -S02-R16, -S02-OR16, S02-NR16Ri7 oderC 1 -C 13 alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, cyano, halogen, nitro or a radical of the formula -CO-OR 16 , -CO-NR 16 R 17 , -S0 2 -R 16 , -S0 2 -OR 16 , S0 2 -NR 16 Ri 7 or
NN
R16 R 16
worin R16 und R17 unabhängig voneinander jeweils für Wasser¬ stoff, C1-C13-Alkyl, das gebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, stehen,in which R 16 and R 17 each independently represent hydrogen, C 1 -C 13 -alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function,
R9 Wasserstoff, Chlor, Cyano, Cι-C8-Alkyl, das durch 1 Sauer- Stoffatom in Etherfunktion unterbrochen sein kann, Cι-C8-Alkoxy, Cι-C8-Alkylthio, gegebenenfalls substituiertes Phenyl, Benzyl, Benzyloxy oder einen Rest der Formel -CO-OR16 oder -CO-NR16R17, worin R16 und R17 jeweils die obengenannte Bedeutung besitzen,R 9 is hydrogen, chlorine, cyano, -C 8 alkyl, which can be interrupted by 1 oxygen atom in ether function, -C 8 alkoxy, -C 8 alkylthio, optionally substituted phenyl, benzyl, benzyloxy or one Rest of the formula -CO-OR 16 or -CO-NR 16 R 17 , in which R 16 and R 17 each have the abovementioned meaning,
R10 Wasserstoff, Cyano, Nitro oder einen Rest der Formel -CO-OR16 oder -CO-NR16R17, worin R16 und R17 jeweils die obengenannteR 10 is hydrogen, cyano, nitro or a radical of the formula -CO-OR 16 or -CO-NR 16 R 17 , wherein R 16 and R 17 are each the above
Bedeutung besitzen, oder R9 und R10 zusammen einen anellierten Benzolring,Have meaning, or R 9 and R 10 together form a fused benzene ring,
R11 Cyano, Nitro, Formyl oder einen Rest der FormelR 11 cyano, nitro, formyl or a radical of the formula
-CO-OR16, -CO-NR16R17, -CH=C-CO-OR 16 , -CO-NR 16 R 17 , -CH = C
CN CNCN CN
-CH=C oder -CH=C-CH = C or -CH = C
CO-OR16 CO-NR16R17 CO-OR 16 CO-NR 16 R 17
worin R16 und R17 jeweils die obengenannte Bedeutung besitzen,where R 16 and R 17 each have the meaning given above,
R12 und R13 unabhängig voneinander jeweils Wasserstoff,R 12 and R 13 are each independently hydrogen,
Cι-C4-Alkyl, Cι-C4-Alkoxy, Chlor, Cyano, Nitro oder einen Rest der Formel -CO-OR16 oder -CO-NR16R17, worin R16 und R17 jeweils die obengenannte Bedeutung besitzen,C 1 -C 4 alkyl, C 1 -C 4 alkoxy, chlorine, cyano, nitro or a radical of the formula -CO-OR 16 or -CO-NR 16 R 17 , where R 16 and R 17 each have the abovementioned meaning,
R14 Wasserstoff, Cι-C4-Alkyl oder Chlor undR 14 is hydrogen, -C 4 alkyl or chlorine and
R15 Cyano oder einen Rest der Formel -CO-OR16 oder -CO-NR16R17, worin R16 und R17 jeweils die obengenannte Bedeutung besitzen, bedeuten.R 15 is cyano or a radical of the formula -CO-OR 16 or -CO-NR 16 R 17 , in which R 16 and R 17 each have the abovementioned meaning.
X1 stellt einen 5- oder 6-gliedrigen carbocyclischen oder hetero- cyclischen, vorzugsweise aromatischen, Rest dar, der gegebenen- falls substituiert ist und benzoanelliert sein kann.X 1 represents a 5- or 6-membered carbocyclic or heterocyclic, preferably aromatic, radical which is optionally substituted and can be benzo-fused.
Reste X1 können sich z.B. von Komponenten aus der Benzol-, Indol- , Chinolin- ,Naphthalin- , Pyrrol- , Thiazol-, Benzimidazol- , Benz- thiazol-, Aminothiophen- oder Pyridinreihe ableiten. Wichtige Reste X1 sind z.B. solche der Formeln Va bis VjResidues X 1 can be derived, for example, from components from the benzene, indole, quinoline, naphthalene, pyrrole, thiazole, benzimidazole, benzothiazole, aminothiophene or pyridine series. Important radicals X 1 are, for example, those of the formulas Va to Vj
Figure imgf000008_0001
Figure imgf000008_0001
(Va) (Vb) (Vc)(Va) (Vb) (Vc)
Figure imgf000008_0002
Figure imgf000008_0002
(Vg) (Vh)(Vg) (Vh)
Figure imgf000008_0003
Figure imgf000008_0003
(Vi) (Vj) worin(Vi) (Vj) where
n für 0 oder 1,n for 0 or 1,
Z1 für Wasserstoff, Cι-Cι3-Alkyl, das gegebenenfalls durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen ist, Hydroxy, C!-C4-Alkoxy, Cι-C4-Alkylsulfonylamino, Cι-C4-Mono- oder Dial- kylaminosulfonylamino oder den Rest -NHCOZ7 oder -NHCO2Z7, wobei Z7 die Bedeutung von Phenyl, Benzyl, Tolyl oder C1-C13- Alkyl, das gegebenenfalls durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen ist, besitzt, Z2 für Wasserstoff, Cι-C4-Alkyl oder Cι-C4-Alkoxy,Z 1 for hydrogen, -CC 3 -alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function, hydroxy, C ! -C 4 -alkoxy, -CC 4 -alkylsulfonylamino, -CC 4 -mono- or dialkylaminosulfonylamino or the rest -NHCOZ 7 or -NHCO 2 Z 7 , where Z 7 has the meaning of phenyl, benzyl, tolyl or C 1 -C 13 - alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function, Z 2 for hydrogen, -C 4 alkyl or -C 4 alkoxy,
Z3 und Z4 unabhängig voneinander jeweils für Wasserstoff, C1-C13- Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, C3-C4-Alkenyl, C5-C7-Cycloalkyl, Phenyl oder Tolyl oder zusammen mit dem sie verbindenden Stickstoffatom für einen 5- oder 6-gliedrigen gesättigten heterocyclischen Rest, der gegebenenfalls weitere Heteroatome enthält,Z 3 and Z 4 are each independently of one another hydrogen, C 1 -C 13 -alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, C 3 -C 4 -alkenyl, C 5 -C 7 -cycloalkyl , Phenyl or tolyl or together with the nitrogen atom connecting them for a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms,
Z5 für Wasserstoff oder C1-C4-Alkyl undZ 5 for hydrogen or C 1 -C 4 alkyl and
Z6 für Wasserstoff, Halogen, Cι-Cι3-Alkyl, gegebenenfalls substi¬ tuiertes Phenyl, gegebenenfalls substituiertes Benzyl, C5-C7-Cycloalkyl, Thienyl, Hydroxy, Ci-C4-Alkoxy, Ci-C4-Alkyl- thio oder Cι-Ci3-Monoalkylamino stehen.Z 6 for hydrogen, halogen, C 1 -C 3 -alkyl, optionally substituted phenyl, optionally substituted benzyl, C 5 -C 7 cycloalkyl, thienyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkyl- thio or -CC 3 -monoalkylamino.
Alle in den obengenannten Formeln auftretenden Alkyl- oder Alkenylgruppen können sowohl geradkettig als auch verzweigt sein.All alkyl or alkenyl groups occurring in the above formulas can be both straight-chain and branched.
Wenn in den obengenannten Formeln substituierte Alkylreste auf¬ treten, so können als Substituenten, sofern nicht anders ver¬ merkt, z.B. Cyclohexyl, gegebenenfalls substituiertes Phenyl, Ci-Cβ-Alkanoyloxy, Ci-Cβ-Alkylaminocarbonyloxy, Ci-Cß-Alkoxy- carbonyl, Ci-Cß-Alkoxycarbonyloxy, wobei die Alkylkette der beiden letztgenannten Reste gegebenenfalls durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen ist und durch Phenyl oder Phenoxy substituiert sein kann, Cyclohexyloxy, Phenoxy, Halogen, Hydroxy oder Cyano in Betracht kommen. Die Alkylreste weisen dabei in der Regel 1 oder 2 Substituenten auf.If substituted alkyl radicals occur in the abovementioned formulas, unless otherwise noted, substituents such as cyclohexyl, optionally substituted phenyl, Ci-Cβ-alkanoyloxy, Ci-Cβ-alkylaminocarbonyloxy, Ci-C ß -alkoxycarbonyl can be used as substituents , Ci-C ß -alkoxycarbonyloxy, where the alkyl chain of the latter two radicals is optionally interrupted by 1 to 3 oxygen atoms in ether function and can be substituted by phenyl or phenoxy, cyclohexyloxy, phenoxy, halogen, hydroxy or cyano. The alkyl radicals generally have 1 or 2 substituents.
Wenn in den obengenannten Formeln Alkylreste auftreten, die durch Sauerstoffatome in Etherfunktion unterbrochen sind, so sind, solche Alkylreste bevorzugt, die durch 1 oder 2 Sauerstoffatome in Etherfunktion unterbrochen sind.If alkyl radicals which are interrupted by oxygen atoms in ether function occur in the formulas mentioned above, preference is given to those alkyl radicals which are interrupted by 1 or 2 oxygen atoms in ether function.
Wenn in den obengenannten Formeln substituierte Cyclohexyl-, Phenyl- oder Pyridylreste auftreten, so können als Substituenten, z.B. Cι-C8-Alkyl, Cι-C8-Alkoxy, Benzyloxy, Halogen, dabei insbe- sondere Chlor oder Brom, Nitro oder Carboxyl in Betracht kommen. Die Cyclohexyl-, Phenyl- oder Pyridylreste weisen dabei in der Regel 1 bis 3 Substituenten auf.If substituted cyclohexyl, phenyl or pyridyl radicals occur in the abovementioned formulas, then substituents, for example C 1 -C 8 -alkyl, C 1 -C 8 alkoxy, benzyloxy, halogen, in particular chlorine or bromine, nitro or carboxyl, can be used be considered. The cyclohexyl, phenyl or pyridyl radicals generally have 1 to 3 substituents.
Alkylreste sind z.B. Methyl, Ethyl, Propyl, Isopropyl, Butyl, Isobutyl, see-Butyl, tert-Butyl, Pentyl, Isopentyl, Neopentyl, tert-Pentyl, Hexyl, 2-Methylpentyl, Heptyl, Octyl, 2 -Ethylhexyl, Isooctyl, Nonyl, Isononyl, Decyl, Isodecyl Undecyl, Dodecyl, Tri- decyl, Isotridecyl, (die Bezeichnungen Isooctyl, Isononyl, Iso- decyl und Isotridecyl, sind Trivialbezeichnungen und stammen von den nach der Oxosynthese erhaltenen Alkoholen - vgl. dazu Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 1, Seiten 290 bis 293, sowie Vol. A 10, Seiten 284 und 285), 2-Methoxyethyl, 2-Ethoxyethyl, 2-Propoxyethyl, 2-Isopropoxyethyl, 2-Butoxyethyl, 2- oder 3-Methoxypropyl, 2- oder 3-Ethoxypropyl, 2- oder 3 -Propoxypropyl, 2- oder 3-Butoxypropyl, 2- oder 4-Meth- oxybutyl, 2- oder 4-Ethoxybutyl, 2- oder 4 -Propoxybutyl, 2- oder 4-Butoxybutyl, 3,6-Dioxaheptyl, 3, 6-Dioxaoctyl, 4, 8-Dioxanonyl, 3, 7 -Dioxaoctyl, 3, 7-Dioxanonyl, 4, 7-Dioxaoctyl, 4, 7-Dioxanonyl, 4, 8-Dioxadecyl, 3 , 6, 8 -Trioxadecyl, 3 , 6,9 -Trioxaundecyl, 3 , 6, 9 , 12-Tetraoxatridecyl, 3, 6, 9, 12-Tetraoxatetradecyl, 2-Meth- oxycarbonylethyl, 2-Ethoxycarbonylethyl, 2-Propoxycarbonylethyl, 2 -Isopropoxycarbonylethyl, 2-Butoxycarbonylethyl, 2- oder 3-Meth- oxycarbonylpropyl, 2- oder 3 -Ethoxycarbonylpropyl, 2- oderExamples of alkyl radicals are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, see-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl , Isononyl, decyl, isodecyl undecyl, dodecyl, tri- decyl, isotridecyl (the names isooctyl, isononyl, iso-decyl and isotridecyl are trivial names derived from those obtained by the oxo process alcohols -. cf. Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol A1, pages 290 to 293, as well as Vol. A 10, pages 284 and 285), 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3, 6-dioxaoctyl, 4, 8-dioxanonyl, 3, 7-dioxaoctyl, 3, 7-dioxanonyl, 4, 7-dioxaoctyl, 4, 7-dioxanonyl, 4, 8-dioxadecyl, 3, 6, 8-trioxadecyl, 3, 6,9-trioxaundecyl, 3, 6, 9, 12-tetraoxatridecyl, 3, 6, 9, 12-tetraoxatetradecyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-isopropoxycarbonylethyl, 2-butoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2- or 3-ethoxycarbonylpropyl, 2- or
3-Propoxycarbonylpropyl, 2- oder 3-Butoxycarbonylpropyl, 2- oder 4 -Methoxycarbonylbutyl, 2- oder 4 -Ethoxycarbonylbutyl, 2- oder3-propoxycarbonylpropyl, 2- or 3-butoxycarbonylpropyl, 2- or 4-methoxycarbonylbutyl, 2- or 4-ethoxycarbonylbutyl, 2- or
4 -Propoxycarbonylbutyl, 2- oder 4 -Butoxycarbonylbutyl, 2-Methoxy- carbonyloxyethyl, 2-Ethoxycarbonyloxyethyl, 2-Propoxycarbonyl- oxyethyl, 2-Isopropoxycarbonyloxyethyl, 2-Butoxycarbonyloxyethyl, 2- oder 3 -Methoxycarbonyloxypropyl, 2- oder 3 -Ethoxycarbonyloxy- propyl, 2- oder 3-Propoxycarbonyloxypropyl, 2- oder 3-Butoxy- carbonyloxypropyl, 2- oder 4-Methoxycarbonyloxybutyl, 2- oder 4-Ethoxycarbonyloxybutyl, 2- oder 4 -Propoxycarbonyloxybutyl, 2- oder 4 -Butoxycarbonyloxybutyl, 2- (2 -Phenylethoxycarbonyl- oxy) ethyl, 2- oder 3- (2-Phenylethoxycarbonyloxy)propyl, 2 - (2 -Ethoxyethoxycarbonyloxy) ethyl, 2- oder 3 - (2-Ethoxyethoxy- carbonyloxy)propyl, 2-Methylaminocarbonyloxyethyl, 2-Ethylamino- carbonyloxyethyl, 2- oder 3 -Methylaminocarbonyloxypropyl, 2- oder 3-Ethylaminocarbonyloxypropyl, 2- oder 4-Methylaminocarbonyloxy- butyl, 2- oder 4-Ethylaminocarbonyloxybutyl, Cyclohexylmethyl, 2-Cyclohexylethyl,Benzyl- 2-Phenylethyl, 2-, 3- oder 4-Methyl- benzyl, 2-, 3- oder 4-Methoxybenzyl, 2-, 3- oder 4 -Nitrobenzyl, 2-Hydroxyethyl, 2- oder 3 -Hydroxypropyl, 2- oder 4-Hydroxybutyl, 2-Cyclohexyloxyethyl, 2- oder 3 -Cyclohexyloxypropyl, 2- oder 4 -Cyclohexyloxybutyl, 2-Phenoxyethyl, 2- oder 3-Phenoxypropyl, 2- oder 4-Phenoxybutyl, Trifluormethyl, 2-Chlorethyl, 2- oder 3-Chlorpropyl, 2-Cyanoethyl, 2- oder 3 -Cyanopropyl oder 2- oder 4 -Cyanobuty1.4-propoxycarbonylbutyl, 2- or 4-butoxycarbonylbutyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-isopropoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2- or 3-methoxycarbonyloxypropyl, 2- or 3-ethoxycarbonyloxypropyl , 2- or 3-propoxycarbonyloxypropyl, 2- or 3-butoxycarbonyloxypropyl, 2- or 4-methoxycarbonyloxybutyl, 2- or 4-ethoxycarbonyloxybutyl, 2- or 4-propoxycarbonyloxybutyl, 2- or 4-butoxycarbonyloxybutyl, 2- (2 - Phenylethoxycarbonyloxy) ethyl, 2- or 3- (2-phenylethoxycarbonyloxy) propyl, 2 - (2-ethoxyethoxycarbonyloxy) ethyl, 2- or 3 - (2-ethoxyethoxycarbonyloxy) propyl, 2-methylaminocarbonyloxyethyl, 2-ethylaminocarbonyloxyethyl , 2- or 3-methylaminocarbonyloxypropyl, 2- or 3-ethylaminocarbonyloxypropyl, 2- or 4-methylaminocarbonyloxybutyl, 2- or 4-ethylaminocarbonyloxybutyl, cyclohexylmethyl, 2-cyclohexylethyl, benzyl-2-phenylethyl, 2-, 3- or 4 Methyl benzyl, 2-, 3- or 4-methoxybenzyl, 2-, 3- or 4-nitrobenzyl, 2-hydroxyethyl, 2- or 3-hydroxypropyl, 2- or 4-hydroxybutyl, 2-cyclohexyloxyethyl, 2- or 3-cyclohexyloxypropyl, 2- or 4-cyclohexyloxybutyl, 2-phenoxyethyl, 2- or 3-phenoxypropyl, 2- or 4-phenoxybutyl, trifluoromethyl, 2-chloroethyl, 2- or 3-chloropropyl, 2-cyanoethyl, 2- or 3-cyanopropyl or 2- or 4-cyanobuty1.
Alkenylreste sind z.B. Prop-1-en-3-yl, But-2 -en-4-yl oder 2-Methylprop-l-en-3 -yl. Cycloalkylreste sind z.B. Cyclopentyl, Methylcyclopentyl, Dimethylcyclopentyl, Cyclohexyl, Methylcyclohexyl oder Cyclo- heptyl.Alkenyl radicals are, for example, prop-1-en-3-yl, but-2-en-4-yl or 2-methylprop-l-en-3-yl. Cycloalkyl radicals are, for example, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl or cycloheptyl.
Phenylreste sind z.B. Phenyl, 2-, 3- oder 4-Methylphenyl, 2-, 3- oder 4-Ethylphenyl, 2-, 3- oder 4 -Propylphenyl, 2-, 3- oder 4 -1sopropylphenyl, 2- , 3- oder 4-Butylphenyl, 2,3-, 2,4- oder 2, 6-Dimethylphenyl, 2-, 3- oder 4-Methoxyphenyl, 2-, 3- oder 4 -Ethoxyphenyl, 2,3-, 2,4- oder 2,6-Dirnethoxypheny1, 2- , 3 - oder 4-Fluorphenyl, 2-, 3- oder 4-Chlorphenyl, 2-, 3- oder 4 -Brom- phenyl oder 2-, 3- oder 4-Nitrophenyl oder 2-, 3- oder 4-Carboxylphenyl.Phenyl radicals are e.g. Phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4 -1sopropylphenyl, 2-, 3- or 4- Butylphenyl, 2,3-, 2,4- or 2, 6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4- or 2, 6-Dirnethoxypheny1, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl, 2-, 3- or 4-bromophenyl or 2-, 3- or 4-nitrophenyl or 2-, 3rd - or 4-carboxylphenyl.
Pyridylreste sind z.B. Pyridyl, 2-, 3- oder 4-Methylpyridyl oder 2-, 3- oder 4-Carboxylpyridyl.Pyridyl residues are e.g. Pyridyl, 2-, 3- or 4-methylpyridyl or 2-, 3- or 4-carboxylpyridyl.
Carbamoylreste sind z.B. Mono- oder Dimethylcarbamoyl, Mono- oder Diethylcarbamoyl, Mono- oder Dipropylcarbamoyl, Mono- oder Diiso- propylcarbamoyl, oder Mono- oder Dibutylcarbamoyl .Carbamoyl residues are e.g. Mono- or dimethylcarbamoyl, mono- or diethylcarbamoyl, mono- or dipropylcarbamoyl, mono- or diisopropylcarbamoyl, or mono- or dibutylcarbamoyl.
Alkylthioreste sind z.B. Methylthio, Ethylthio, Propylthio, Isopropylthio, Butylthio, Isobutylthio, Pentylthio, Hexylthio, Heptylthio, Octylthio, Isooctylthio, 2-Ethylhexylthio, Nonylthio, Isononylthio, Decylthio oder Isodecylthio.Alkylthio residues are e.g. Methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, pentylthio, hexylthio, heptylthio, octylthio, isooctylthio, 2-ethylhexylthio, nonylthio, isononylthio, decylthio or isodecylthio.
Alkoxyreste sind z.B. Methoxy, Ethoxy, Propoxy, Isopropoxy, Butoxy, Isobutoxy, sec-Butoxy, Pentyloxy, Isopentyloxy, Neo- pentyloxy, tert-Pentyloxy, Hexyloxy, 2-Methylpentyloxy, Heptyl- oxy, Octyloxy, Isooctyloxy oder 2-Ethylhexyloxy.Alkoxy residues are e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, isooctyloxy or 2-ethylhexyloxy.
Halogen ist z.B. Fluor, Chlor oder Brom.Halogen is e.g. Fluorine, chlorine or bromine.
Alkylsulfonyl- , Cycloalkylsufonyl- , Phenylsulfonyl- und Pyridyl- sulfonylreste sind z.B. Methylsulfonyl, Ethylsulfonyl, Propyl- sulfonyl, Isopropylsulfonyl, Butylsulfonyl, Isobutylsulfonyl, sec-Butylsulfonyl, Pentylsulfonyl, Isopentylsulfonyl, Neopentyl- sulfonyl, Hexylsulfonyl, Heptylsulfonyl, Octylsulfonyl, 2-Ethyl¬ hexylsulfonyl, Cyclopentylsulfonyl, Cyclohexylsulfonyl, Cyclohep- tylsulfonyl, Phenylsulfonyl, 2-Methylphenylsulfonyl, 2-Methoxy- phenylsulfonyl, 2-Chlorphenylsulfony, 2-Nitrophenylsulfonyl, Pyridylsulfonyl oder 2-, 3- oder 4-Methylpyridylsulfonyl .Alkylsulfonyl, cycloalkylsufonyl, phenylsulfonyl and pyridylsulfonyl radicals are e.g. Methylsulfonyl, ethylsulfonyl, propyl sulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, pentylsulfonyl, Isopentylsulfonyl, neopentyl sulfonyl, hexylsulfonyl, Heptylsulfonyl, octylsulfonyl, 2-Ethyl¬ hexylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptane tylsulfonyl, phenylsulfonyl, 2- Methylphenylsulfonyl, 2-methoxyphenylsulfonyl, 2-chlorophenylsulfony, 2-nitrophenylsulfonyl, pyridylsulfonyl or 2-, 3- or 4-methylpyridylsulfonyl.
Alkoxycarbonylreste sind z.B. Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl, Isopropoxycarbonyl, Butoxycarbonyl, Isobutoxy- carbonyl, sec-Butoxycarbonyl, Pentyloxycarbonyl, Isopentyloxy- carbonyl, Neopentyloxycarbonyl, Hexyloxycarbonyl, Heptyloxy- carbonyl, Octyloxycarbonyl, Isooctyloxycarbonyl oder 2-Ethyl- hexyloxycarbonyl.Alkoxycarbonyl radicals are, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, hexyloxycarbonyl, heptyloxy- carbonyl, octyloxycarbonyl, isooctyloxycarbonyl or 2-ethylhexyloxycarbonyl.
Alkanoyl- und Benzoylreste sind z.B. Formyl, Acetyl, Propionyl, Butyryl, Pentanoyl, Hexanoyl, Benzoyl, 2-, 3- oder 4-Methyl- benzoyl, 2-, 3- oder 4-Methoxybenzoyl, 2-, 3- oder 4 -Chlorbenzoyl oder 2-, 3- oder 4-Nitrobenzoyl.Alkanoyl and benzoyl residues are e.g. Formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, benzoyl, 2-, 3- or 4-methylbenzoyl, 2-, 3- or 4-methoxybenzoyl, 2-, 3- or 4-chlorobenzoyl or 2-, 3rd - or 4-nitrobenzoyl.
Alkylsulfonylamino- und Mono- oder Dialkylaminosulfonylaminoreste sind z.B. Methylsulfonylamino, Ethylsulfonylamino, Propyl- sulfonylamino, Isopropylsulfonylamino, Butylsulfonylamino, Mono- oder Dimethylaminosulfonylamino, Mono- oder Diethylaminosulfonyl- amino, Mono- oder Dipropylaminosulfonylamino, Mono- oder Diiso- propylaminosulfonylamino, Mono- oder Dibutylaminosulfonylamino oder (N-Methyl-N-ethylaminosulfonyl) amino.Alkylsulfonylamino and mono- or dialkylamino sulfonylamino residues are e.g. Methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino, mono- or dimethylaminosulfonylamino, mono- or diethylaminosulfonylamino, mono- or dipropylaminosulfonylamino, mono- or diisopropylamino-sulfonylamino-nylamosulfonylamino-nylamino-naphonamino-nylamino-naphonamino- amino.
Alkoxyreste sind z.B. Methoxy, Ethoxy, Propoxy, Isopropoxy, Butoxy, Isobutoxy, sec-Butoxy, tert-Butoxy, Pentyloxy, Isopenty- loxy, Neopentyloxy, tert-Pentyloxy, Hexyloxy, Heptyloxy, Octyl- oxy, Isooctyloxy, 2 -Ethylhexyloxy, Nonyloxy, Isononyloxy, Decyl- oxy, Isodecyloxy, 2-, 3- oder 4-Methylbenzyloxy, 2- (2-, 3- oder 4-Methylphenyl) ethoxy.Alkoxy residues are e.g. Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, heptyloxy, octyloxy, isooctyloxy, 2-ethylhexyloxy, nonyloxy, isononyloxy, Decyloxy, isodecyloxy, 2-, 3- or 4-methylbenzyloxy, 2- (2-, 3- or 4-methylphenyl) ethoxy.
Sulfamoylreste sind z.B. Methylsulfamoyl, Ethylsulfamoyl, Propyl- sulfamoyl, Isopropylsulfamoyl, Butylsulfamoyl, Pentylsulfamoyl, Hexylsulfamoyl, Heptylsulfamoyl, Octylsulfamoyl, 2-Ethylhexyl- sulfamoyl, 2-Methoxyethylsulfamoyl, 2-Ethoxyethylsulfamoyl, 2- oder 3 -Methoxypropylsulfamoyl, 2- oder 3-Ethoxypropyl- sulfamoyl, 3,6-Dioxaheptylsulfamoyl oder 2 -Ethoxyethylsulfamoyl, 3, 6-Dioxaoctylsulfamoyl.Sulfamoyl residues are e.g. Methylsulfamoyl, ethylsulfamoyl, propylsulfamoyl, isopropylsulfamoyl, butylsulfamoyl, pentylsulfamoyl, hexylsulfamoyl, heptylsulfamoyl, octylsulfamoyl, 2-ethylhexylsulfamoyl, 2-methoxyethylsulfamoyloxamoyl, 3-ethoxysulfamoyl, 3-ethoxysulfamoyl, or 3,6-dioxaheptylsulfamoyl or 2-ethoxyethylsulfamoyl, 3, 6-dioxaoctylsulfamoyl.
Wenn die Reste E1 und E2 oder Z3 und Z4 jeweils zusammen mit dem sie verbindenden Stickstoffatom einen 5- oder 6-gliedrigen gesät¬ tigten heterocyclischen Rest, der gegebenenfalls weitere Hetero- atome enthält, bedeuten, so können dafür z.B. Pyrrolidinyl,If the radicals E 1 and E 2 or Z 3 and Z 4 , together with the nitrogen atom connecting them, each represent a 5- or 6-membered saturated heterocyclic radical which optionally contains further hetero atoms, for example pyrrolidinyl,
Piperidinyl, Morpholinyl, Thiomorpholinyl, Thiomorpholinyl-S, S- dioxid, Piperazinyl oder N- (Cι-C4-Alkyl)piperazinyl, wie N-Methyl- oder N-Ethylpiperazinyl, in Betracht kommen.Piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl-S, S-dioxide, piperazinyl or N- (-CC 4 -alkyl) piperazinyl, such as N-methyl or N-ethylpiperazinyl, come into consideration.
Bevorzugte Mischungspartner sind Pyridonfarbstoffe der Formel I, in der X2 Cyano bedeutet.Preferred mixture partners are pyridone dyes of the formula I in which X 2 is cyano.
Bevorzugte Mischungspartner sind weiterhin Pyridonfarbstoffe der Formel I, in der X3 C1-C13-Alkyl, das gegebenenfalls durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen ist, bedeutet. Besonders bevorzugte Mischungspartner sind Pyridonfarbstoffe der Formel I, in der X3 Ci-Cß-Alkyl, das gegebenenfalls durch 1 oder 2 Sauerstoffatome in Etherfunktion unterbrochen ist, bedeutet.Preferred mixture partners are furthermore pyridone dyes of the formula I in which X 3 is C 1 -C 13 -alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function. Particularly preferred mixture partners are pyridone dyes of the formula I in which X 3 denotes Ci-C ß- alkyl, which is optionally interrupted by 1 or 2 oxygen atoms in ether function.
Weiterhin bevorzugte Mischungspartner sind Pyridonfarbstoffe der Formel I, in der X1 einen Rest bedeutet, der sich von einer Kompo¬ nente aus der Thiazol- oder Indolreihe ableitet, insbesondere einen Rest der Formel Vi oder Vj .Further preferred mixing partners are pyridone dyes of the formula I in which X 1 is a radical which is derived from a component from the thiazole or indole series, in particular a radical of the formula Vi or Vj.
Besonders hervorzuheben als Mischungspartner sind Pyridon- farbstoffe der Formel laParticularly noteworthy as mixing partners are pyridone dyes of the formula la
ü
Figure imgf000013_0001
ü
Figure imgf000013_0001
in derin the
X3 Cι-C8-Alkyl,X 3 -CC 8 alkyl,
Z3 und Z4 unabhängig voneinander jeweils Cι-C8-Alkyl, das gegebenenfalls durch Cι-C4-Alkoxy, Cι-C4-Alkoxycarbonyl oder Phenyl substituiert ist, Cyclopentyl, Cyclohexyl oder Prop-l-en-3-yl undZ 3 and Z 4 are each independently of one another C 1 -C 8 -alkyl, which is optionally substituted by C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or phenyl, cyclopentyl, cyclohexyl or prop-l-en-3-yl and
Z6 verzweigtes C3-C10-Alkyl oder Phenyl, insbesondere verzweigtes C3-C8-Alkyl bedeuten.Z 6 is branched C 3 -C 10 alkyl or phenyl, in particular branched C 3 -C 8 alkyl.
Ganz besonders hervorzuheben als Mischungspartner sind Pyridon- farbstoffe der Formel la, in der Z6 verzweigtes C3-C6-Alkyl, ins- besondere verzweigtes C5-Alkyl bedeutet, wobei Neopentyl besonders zu nennen ist.Particularly noteworthy as mixing partners are pyridone dyes of the formula Ia in which Z 6 is branched C 3 -C 6 -alkyl, in particular branched C 5 -alkyl, neopentyl being particularly mentioned.
Weiterhin ganz besonders hervorzuheben als Mischungspartner sind Pyridonfarbstoffe der Formel la, in der, wenn die Reste Z3 und Z4 jeweils Cι-C8-Alkyl bedeuten, die Summe der in den beiden Resten Z3 und Z4 vorhandenen Kohlenstoffatome mindestens 7, insbesondere mindestens 8, beträgt. Weiterhin ganz besonders hervorzuheben als Mischungspartner sind Pyridonfarbstoffe der Foremi lbAlso particularly to be emphasized as a mixture partner are pyridone dyes of the formula Ia, in which, when the Z 3 and Z 4 radicals are each C 1 -C 8 -alkyl, the sum of the carbon atoms present in the two Z 3 and Z 4 radicals is at least 7, in particular is at least 8. Also particularly noteworthy as mixing partners are pyridone dyes from Foremi lb
Figure imgf000014_0001
Figure imgf000014_0001
in der X3 und Z3 unabhängig voneinander jeweils Cι-C8-Alkyl bedeuten.in which X 3 and Z 3 each independently represent C 1 -C 8 -alkyl.
Bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der R4 Methyl und R1, R2 und R3 unabhängig voneinander jeweils Wasserstoff oder C1-C13-Alkyl, das gegebenenfalls durch Hydroxy, Acetyloxy, Cyano oder Phenyl substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, dedeuten.Preferred mixture partners are azo dyes of the formula II in which R 4 is methyl and R 1 , R 2 and R 3 are each, independently of one another, hydrogen or C 1 -C 13 -alkyl which is optionally substituted by hydroxy, acetyloxy, cyano or phenyl and by 1 up to 3 oxygen atoms can be interrupted in ether function.
Besonders interessante Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVa, IVb, IVc, IVd, IVe, IVf oder IVg gehorcht.Particularly interesting mixture partners are azo dyes of the formula II, in which the radical D is derived from a diazo component which obeys the formula IVa, IVb, IVc, IVd, IVe, IVf or IVg.
Weiterhin bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVa, IVb, IVd oder IVf gehorcht, wo¬ bei R6, R7 und R8 unabhängig voneinander jeweils Wasserstoff, Ci-Cio-Alkyl, das durch 1 oder 2 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch Cι-C4-Alkoxy- carbonyl oder Cι-C4-Alkanoyloxy substituiert ist, Cyano, Halogen, Nitro oder einen Rest der Formel -CO-OR18, -C0-NR18R19, -S02-R18, -S02-OR18 oder -S02-NR18R19, worin R19 und R20 unabhängig vonein- ander jeweils für Wasserstoff oder C1-C10-Alkyl, das durch 1 oder 2 Sauerstoffatome in Etherfunktion unterbrochen sein kann und gegebenenfalls durch C1-C4-Alkoxycarbonyl oder Cι-C4-Alkanoyloxy substituiert ist, stehen, bedeuten.Mixing partners which are further preferred are azo dyes of the formula II in which the radical D is derived from a diazo component which obeys the formula IVa, IVb, IVd or IVf, where R 6 , R 7 and R 8 each independently of one another are hydrogen, Ci Cio-alkyl, which may be interrupted by 1 or 2 oxygen atoms in ether function and optionally substituted by -C 4 alkoxycarbonyl or C -C 4 alkanoyloxy, cyano, halogen, nitro or a radical of the formula -CO-OR 18 , -C0-NR 18 R 19 , -S0 2 -R 18 , -S0 2 -OR 18 or -S0 2 -NR 18 R 19 , where R 19 and R 20 are each independently of one another hydrogen or C 1 - C1 0 alkyl which may be interrupted by 1 or 2 oxygen atoms in ether function and optionally substituted by C 1 -C 4 -alkoxycarbonyl or Cι-C 4 alkanoyloxy substituted, stand, mean.
Weiterhin bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVc gehorcht, wobeiFurther preferred mixture partners are azo dyes of the formula II in which the radical D is derived from a diazo component which obeys the formula IVc, where
R9 Wasserstoff, Chlor, Cι-C8-Alkyl, gegebenenfalls durch C!-C4-Alkyl oder Cι~C4-Alkoxy substituiertes Phenyl oder Benzyl, R10 Cyano oder einen Rest der Formel -CO-OR18 oder -CO-NR18R19, worin R18 und R19 jeweils die obengenannte Bedeutung besitzen undR 9 is hydrogen, chlorine, -CC 8 alkyl, optionally by C ! -C 4 alkyl or -C ~ C4-alkoxy substituted phenyl or benzyl, R 10 cyano or a radical of the formula -CO-OR 18 or -CO-NR 18 R 19 , wherein R 18 and R 19 each have the abovementioned meaning and
R11 einen Rest der FormelR 11 is a radical of the formula
CN CN CNCN CN CN
-CH=C -CH=C oder -CH=C-CH = C -CH = C or -CH = C
\ \ \ CN CO-OR18 CO-NR18R19 worin R18 und R19 jeweils die obengenannte Bedeutung besitzen, bedeuten.\ \ \ CN CO-OR 18 CO-NR 18 R 19 in which R 18 and R 19 each have the abovementioned meaning.
Weiterhin bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVe gehorcht, wobeiFurther preferred mixing partners are azo dyes of the formula II in which the radical D is derived from a diazo component which obeys the formula IVe, where
R9 Wasserstoff, Chlor, Cι-C8-Alkyl, gegebenenfalls durch Cι-C4-Alkyl oder C1-C4-Alkoxy substituiertes Phenyl oder Benzyl undR 9 is hydrogen, chlorine, Cι-C8 alkyl, optionally substituted by Cι-C 4 alkyl or C 1 -C 4 -alkoxy-substituted phenyl or benzyl and
R11 Cyano, Nitro, Formyl oder einen Rest der Formel -CO-OR18, wobei R18 die obengenannte Bedeutung besitzt, bedeuten.R 11 is cyano, nitro, formyl or a radical of the formula -CO-OR 18 , where R 18 has the meaning given above.
Weiterhin bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVg gehorcht, wobeiFurther preferred mixture partners are azo dyes of the formula II in which the radical D is derived from a diazo component which obeys the formula IVg, where
R9 Ci-Cß-Alkyl, das durch 1 Sauerstoffatom in Etherfunktion unterbrochen sein kann, Ci-Cβ-Alkoxy, gegebenenfalls durch Cι-C4-Alkyl oder Cι-C4-Alkoxy substituiertes Phenyl, Benzyl oder Benzyloxy undR 9 Ci-C ß- alkyl, which can be interrupted by 1 oxygen atom in ether function, Ci-Cβ-alkoxy, optionally substituted by Cι-C 4 alkyl or Cι-C 4 alkoxy phenyl, benzyl or benzyloxy and
R10 Cyano, Nitro oder den Rest der Formel -CO-OR18, wobei R18 die obengenannte Bedeutung besitzt, bedeuten.R 10 is cyano, nitro or the rest of the formula -CO-OR 18 , where R 18 has the abovementioned meaning.
Besonders bevorzugte Mischungspartner sind Azofarbstoffe der Formel II, in der der Rest D sich von einer Diazokomponente ableitet, die der Formel IVc gehorcht, wobeiParticularly preferred mixture partners are azo dyes of the formula II, in which the radical D is derived from a diazo component which obeys the formula IVc, where
R9 Wasserstoff, Chlor, Cι-C8-Alkyl, das durch 1 Sauerstoffatom in Etherfunktion unterbrochen sein kann, Cι-C8-Alkoxy, gegebenen¬ falls durch Cι-C4-Alkyl oder Cι-C4-Alkoxy substituiertes Phenyl, Benzyl oder den Rest der Formel -CO-OR18, wobei R18 die obengenannte Bedeutung besitzt, R10 Cyano oder den Rest der Formel -CO-OR18, wobei R18 die obenge¬ nannte Bedeutung besitzt undR 9 is hydrogen, chlorine, C 1 -C 8 -alkyl, which can be interrupted by 1 oxygen atom in ether function, C 1 -C 8 -alkoxy, phenyl optionally substituted by C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, Benzyl or the rest of the formula -CO-OR 18 , where R 18 has the meaning given above, R 10 cyano or the rest of the formula -CO-OR 18 , where R 18 has the meaning given above and
R11 Cyano, Nitro, Formyl oder den Rest der Formel -CO-OR18, wobei R18 die obengenannte Bedeutung besitzt, bedeuten.R 11 is cyano, nitro, formyl or the radical of the formula -CO-OR 18 , where R 18 has the meaning given above.
Bevorzugte Mischungspartner sind Anthrachinonfarbstoffe der Formel III, in der L1 Wasserstoff und L4 Hydroxy bedeuten und L2 und L3 jeweils die obengenannte Bedeutung besitzen.Preferred mixture partners are anthraquinone dyes of the formula III in which L 1 is hydrogen and L 4 is hydroxy and L 2 and L 3 each have the abovementioned meaning.
1010
Bevorzugte Mischungspartner sind weiterhin Anthrachinonfarbstoffe der Formel III, in der L2 und/oder L3 einen Rest der FormelPreferred mixture partners are also anthraquinone dyes of the formula III, in which L 2 and / or L 3 is a radical of the formula
Figure imgf000016_0001
Figure imgf000016_0001
bedeuten, worin G1 und G2 jeweils die obengenannte Bedeutung besitzen. 20mean, in which G 1 and G 2 each have the abovementioned meaning. 20th
Bevorzugte Mischungspartner sind weiterhin Anthrachinonfarbstoffe der Formel lilaPreferred mixture partners are also anthraquinone dyes of the formula purple
Figure imgf000016_0002
Figure imgf000016_0002
30 ° 0H 30 ° 0H
in der G1 und G2 jeweils die obengenannte Bedeutung besitzen.in which G 1 and G 2 each have the meaning given above.
Die erfindungsgemäßen Farbstoffmischungen enthalten in der Regel 35 20 bis 80 Gew.%, vorzugsweise 30 bis 70 Gew.% und insbesondere 40 bis 60 Gew.%, jeweils bezogen auf das Gewicht der Farbstoff- mischung, einen oder mehrere Pyridonfarbstoffe der Formel I sowie 20 bis 80 Gew.%, vorzugsweise 30 bis 70 Gew.% und insbesondere 40 bis 60 Gew.%, jeweils bezogen auf das Gewicht der Farbstoff- 40 mischung, einen oder mehrere Azofarbstoffe der Formel II und/oder Anthrachinonfarbstoffe der Formel III.The dye mixtures according to the invention generally contain 35 to 80% by weight, preferably 30 to 70% by weight and in particular 40 to 60% by weight, in each case based on the weight of the dye mixture, one or more pyridone dyes of the formula I and 20 up to 80% by weight, preferably 30 to 70% by weight and in particular 40 to 60% by weight, in each case based on the weight of the dye mixture, one or more azo dyes of the formula II and / or anthraquinone dyes of the formula III.
Die neuen Farbstoffmischungen können nach an sich bekannten Methoden, z.B. durch Abmischen der Einzelfarbstoffe im oben- 45 genannten Gewichtsverhältnis erhalten werden. Die Pyridonfarbstoffe der Formel I sind bekannt und z.B. in der WO-A-96/15195 sowie in der deutschen Patentanmeldung 196 48 564.9 beschrieben.The new dye mixtures can be obtained by methods known per se, for example by mixing the individual dyes in the weight ratio mentioned above. The pyridone dyes of the formula I are known and are described, for example, in WO-A-96/15195 and in German patent application 196 48 564.9.
Die Azofarbstoffe der Formel II sind ebenfalls an sich bekannt und z.B. in der US-A-4 939 118 oder US-A-5 403 363 beschrieben oder können nach den dort genannten Methoden erhalten werden.The azo dyes of formula II are also known per se and e.g. in US-A-4 939 118 or US-A-5 403 363 or can be obtained by the methods mentioned therein.
Die Anthrachinonfarbstoffe der Formel III sind ebenfalls an sich bekannt und beispielsweise in K. Venkataraman "The Chemistry of Synthetic Dyes", Vol. III, Seiten 391 bis 413, Academic Press, New York, London, 1970, beschrieben.The anthraquinone dyes of the formula III are also known per se and are described, for example, in K. Venkataraman "The Chemistry of Synthetic Dyes", Vol. III, pages 391 to 413, Academic Press, New York, London, 1970.
Die erfindungsgemäßen Farbstoffmischungen zeichnen sich durch vorteilhafte anwendungstechnische Eigenschaften aus. Sie weisen eine hohe Löslichkeit im Farbband (gute Kompatibilität mit dem Bindemittel) , eine hohe Stabilität in der Druckfarbe, eine gute Transferierbarkeit, eine hohe Bildstabilität (d.h. gute Licht¬ echtheit sowie gute Stabilität gegenüber Umwelteinflüssen, z.B. Feuchtigkeit, Temperatur oder Chemikalien) auf und gewährleisten eine flexible coloristische Anpassung an die restlichen subtrak- tiven Grundfarben, wodurch hochwertige Farbenräume resultieren.The dye mixtures according to the invention are distinguished by advantageous performance properties. They have high solubility in the ink ribbon (good compatibility with the binder), high stability in the printing ink, good transferability, high image stability (ie good light fastness and good stability against environmental influences, for example moisture, temperature or chemicals) and ensure flexible coloristic adaptation to the remaining subtractive primary colors, resulting in high-quality color spaces.
Insbesondere hervorzuheben ist die spektral gleichmäßige Abnahme der Einzelkomponenten bei Bestrahlung, d.h. der Einzelfarbstoff mit der geringeren Lichtechtheit nimmt in der Regel nicht bevor¬ zugt ab.Of particular note is the spectrally uniform decrease in the individual components when irradiated, i.e. the individual dye with the lower light fastness generally does not preferably decrease.
Bei allen im folgenden aufgeführten Anwendungsgebieten ergeben die erfindungsgemäßen Farbstoffmischungen Drucke oder Färbungen, die sehr brillant, farbstark und stabil sind.In all the fields of application listed below, the dye mixtures according to the invention produce prints or dyeings which are very brilliant, strong in color and stable.
Ein weiterer Gegenstand der vorliegenden Erfindung ist ein Ver¬ fahren zur Übertragung von Farbstoffen von einem Träger auf ein mit Kunststoff beschichtetes Papier durch Diffusion oder Subli¬ mation mit Hilfe einer Energiequelle, das dadurch gekennzeichnet ist, daß man einen Träger verwendet, auf dem sich eine eingangs näher bezeichnete Farbstoffmischung befindet.Another object of the present invention is a method for transferring dyes from a support to a plastic-coated paper by diffusion or sublimation with the aid of an energy source, which is characterized in that a support is used on which a dye mixture specified at the beginning.
Zur Herstellung der für das erfindungsgemäße Verfahren benötigten Farbstoffträger werden die Farbstoffmischungen in einem geeigneten organischen Lösungsmittel oder in Mischungen von Lösungsmitteln mit einem oder mehreren Bindemitteln, gegebenen¬ falls unter Zugabe von Hilfsmitteln, zu einer Druckfarbe ver- arbeitet. Diese enthält die Farbstoffe vorzugsweise in molekular¬ dispers gelöster Form. Die Druckfarbe kann mittels einer Rakel auf den inerten Träger aufgetragen und die Färbung an der Luft getrocknet werden. Geeignete organische Lösungsmittel für die Farbstoffmischungen sind z.B. solche, in denen die Löslichkeit der Farbstoffmischungen bei einer Temperatur von 20°C größer als 1 Gew. -%, vorzugsweise größer als 5 Gew. -% ist.To produce the dye carrier required for the process according to the invention, the dye mixtures are processed into a printing ink in a suitable organic solvent or in mixtures of solvents with one or more binders, if appropriate with the addition of auxiliaries. This contains the dyes preferably in a molecularly disperse dissolved form. The printing ink can be applied to the inert carrier by means of a squeegee and the coloring in air be dried. Suitable organic solvents for the dye mixtures are, for example, those in which the solubility of the dye mixtures at a temperature of 20 ° C. is greater than 1% by weight, preferably greater than 5% by weight.
Beispielhaft seien Ethanol, Propanol, Isobutanol, Tetrahydro- furan, Methylenchlorid, Methylethylketon, Cyclopentanon, Cyclo- hexanon, Toluol, Chlorbenzol oder deren Mischungen genannt.Examples include ethanol, propanol, isobutanol, tetrahydrofuran, methylene chloride, methyl ethyl ketone, cyclopentanone, cyclohexanone, toluene, chlorobenzene or mixtures thereof.
Als Bindemittel kommen alle Resins oder Polymermaterialien in Betracht, die in organischen Lösungsmitteln löslich sind und die die Farbstoffmischungen an den inerten Träger abriebfest zu bin¬ den vermögen. Dabei werden solche Bindemittel bevorzugt, die die Farbstoffmischung nach Trocknung der Druckfarbe an der Luft in Form eines klaren, transparenten Films aufnehmen, ohne daß dabei eine sichtbare Auskristallisation der Farbstoffmischung auftritt.Suitable binders are all resins or polymer materials which are soluble in organic solvents and which are able to bind the dye mixtures to the inert support in an abrasion-resistant manner. Preference is given to binders which, after the printing ink has dried in air, absorb the dye mixture in the form of a clear, transparent film without any visible crystallization of the dye mixture.
Solche Bindemittel sind beispielsweise in der US-A-5 132 438 oder in den entsprechenden dort zitierten Patentanmeldungen genannt. Darüber hinaus sind gesättigte lineare Polyester zu nennen.Such binders are mentioned, for example, in US Pat. No. 5,132,438 or in the corresponding patent applications cited therein. Saturated linear polyesters should also be mentioned.
Bevorzugte Bindemittel sind Ethylcellulose, Ethylhydroxyethyl- cellulose, Polyvinylbutyral, Polyvinylacetat, Cellulosepropionat oder gesättigte lineare Polyester.Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyral, polyvinyl acetate, cellulose propionate or saturated linear polyesters.
Das Gewichtsverhältnis Bindemittel: Farbstoffmischung beträgt im allgemeinen 1:1 bis 10:1.The weight ratio of binder: dye mixture is generally 1: 1 to 10: 1.
Als Hilfsmittel kommen z.B. Trennmittel in Betracht, wie sie in der US-A-5 132 438 oder den entsprechend dort zitierten Patent¬ anmeldungen genannt sind. Darüber hinaus sind besonders orga¬ nische Additive zu nennen, welche das Auskristallisieren der Transferfarbstoffe bei Lagerung oder beim Erhitzen des Farbbandes verhindern, z.B. Cholesterin oder Vanillin.As aids, e.g. Release agents into consideration, such as those mentioned in US Pat. No. 5,132,438 or the patent applications cited there accordingly. Organic additives which prevent the transfer dyes from crystallizing out during storage or when the ink ribbon is heated, e.g. Cholesterol or vanillin.
Geeignete inerte Träger sind z.B. in der US-A-5 132 438 oder in den entsprechenden dort zitierten Patentanmeldungen beschrieben. Die Dicke des Trägers beträgt im allgemeinen 3 bis 30 μm, Vorzugs weise 5 bis 10 μm.Suitable inert carriers are e.g. in US-A-5 132 438 or in the corresponding patent applications cited therein. The thickness of the carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
Als Farbstoffnehmerschicht kommen prinzipiell alle temperatur¬ stabilen Kunststoffschichten mit Affinität zu den zu trans¬ ferierenden Farbstoffen in Betracht, z.B. modifizierte Poly- carbonate oder Polyester. Weitere Einzelheiten dazu können z.B, aus der US-A-5 132 438 oder den entsprechenden dort zitierten Patentanmeldungen entnommen werden. Die Übertragung erfolgt mittels einer Energiequelle, z.B. mittels eines Lasers oder eines Thermokopfes, wobei letzterer auf eine Temperatur von > 300°C aufheizbar sein muß, damit der Farbstoff- transfer im Zeitbereich t: 0 < t < 15 msec erfolgen kann. Dabei migriert der Farbstoff aus dem Transferblatt und diffundiert in die Oberflächenbeschichtung des Aufnahmemediums .In principle, all temperature-stable plastic layers with an affinity for the dyes to be transferred, for example modified polycarbonates or polyester, are suitable as the dye receiver layer. Further details can be found, for example, in US Pat. No. 5,132,438 or the corresponding patent applications cited therein. The transfer takes place by means of an energy source, for example by means of a laser or a thermal head, the latter having to be able to be heated to a temperature of> 300 ° C. so that the dye transfer can take place in the time range t: 0 <t <15 msec. The dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
Die erfindungsgemaßen Farbstoffmischungen eignen sich weiterhin vorteilhaft zum Färben oder Bedrucken von synthetischen Materia- lien, z.B. von Polyestern, Polyamiden oder Polycarbonaten. Ins¬ besondere zu nennen sind textile Materialien, wie Fasern, Garne, Zwirne, Maschenware, Webware oder Non-wovens aus Polyester, modi¬ fiziertem Polyester, z.B. anionisch modifiziertem Polyester, oder Mischgewebe von Polyester mit Cellulose, Baumwolle, Viskose oder Wolle. Die Färbe- und Druckbedingungen, die auch das Färben in überkritischen Kohlendioxid einschließen, sind an sich bekannt.The dye mixtures according to the invention are furthermore advantageously suitable for dyeing or printing synthetic materials, e.g. of polyesters, polyamides or polycarbonates. Particular mention should be made of textile materials, such as fibers, yarns, twists, knitwear, woven goods or non-wovens made of polyester, modified polyester, e.g. anionically modified polyester, or blended fabrics of polyester with cellulose, cotton, viscose or wool. The dyeing and printing conditions, which also include dyeing in supercritical carbon dioxide, are known per se.
Vorteilhaft eignen sich die neuen Farbstoffmischungen auch zum Bedrucken von Materialien mittels des Ink-Jet-Verfahrens. Geeignete Substrate sind dabei neben den oben genannten, z.B. Papier, Glas, Keramik, Kunststoffe oder Metalle.The new dye mixtures are also advantageously suitable for printing on materials using the ink jet process. Suitable substrates are in addition to the above, e.g. Paper, glass, ceramics, plastics or metals.
Die erfindungsgemäßen Farbstoffe können auch zum Färben von kera- tinischen Fasern, z.B. bei der Haarfärbung oder der Färbung von Pelzen, verwendet werden.The dyes according to the invention can also be used to dye ceramic fibers, e.g. in hair dyeing or dyeing furs.
Die neuen Farbstoffmischungen eignen sich weiterhin vorteilhaft für die Herstellung von Farbfiltern, wie sie z.B. in der EP-A-399 473 beschrieben sind.The new dye mixtures are furthermore advantageously suitable for the production of color filters, such as those e.g. are described in EP-A-399 473.
Schließlich können sie auch vorteilhaft als Farbmittel für die Herstellung von Tonern für die Elektrophotographie verwendet werden.Finally, they can also be used advantageously as colorants for the production of toners for electrophotography.
Die folgenden Beispiele sollen die Erfindung näher erläutern.The following examples are intended to explain the invention in more detail.
Im folgenden sind zunächst die Einzelfarbstoffe aufgeführt, die als Mischungspartner dienten. Tabelle 1The individual dyes that served as mixing partners are listed below. Table 1
Figure imgf000020_0001
Figure imgf000020_0001
Figure imgf000020_0002
Figure imgf000021_0001
Figure imgf000022_0001
*- v© o
Figure imgf000020_0002
Figure imgf000021_0001
Figure imgf000022_0001
* - v © o
Figure imgf000023_0001
Figure imgf000023_0001
eoeo
vo o vo o
Tabelle 2Table 2
Figure imgf000024_0001
Figure imgf000024_0001
Figure imgf000024_0003
Figure imgf000024_0003
Tabelle 3Table 3
Figure imgf000024_0002
Figure imgf000024_0002
Figure imgf000024_0004
Farbstoff Nr. 29
Figure imgf000024_0004
Dye No. 29
22
Figure imgf000025_0001
Figure imgf000025_0001
Tabel le 4Table 4
Färb s tof f mi s chungenDyestuffs
Figure imgf000025_0002
Figure imgf000025_0002
Figure imgf000026_0001
Figure imgf000026_0001
Vorschrift für die thermische Übertragung:Regulation for thermal transfer:
a) 10 g Farbstoffmischung werden, gegebenenfalls unter kurz¬ zeitigem Erwärmen auf 80 bis 90°C, in 100 g einer 10 gew. -%igen Lösung eines Bindemittels auf Basis von Polyvinylbutyral in einem Methylethylketon/Toluol/Cyclo- hexanon-Gemisch (4,5:2:2 v/v/v) eingerührt.a) 10 g of dye mixture, optionally with brief heating to 80 to 90 ° C, in 100 g of a 10 wt. -% solution of a binder based on polyvinyl butyral in a methyl ethyl ketone / toluene / cyclohexanone mixture (4.5: 2: 2 v / v / v) stirred.
Das Gemisch wird mit einer 10 μm Rakel auf eine Polyester- folie von 6 μm Dicke, auf deren Rückseite eine geeignete Gleitschicht aufgebracht ist, aufgerakelt und mit einem Föhn i Minute trockengeblasen. Bevor das Farbband verdruckt werden kann, muß es mindestens 24 Stunden an der Luft nachtrocknen, da Restlösungsmittel den Druckvorgang beeinträchtigen können. Die Farbbänder werden auf einer rechnergesteuerten Versuchs- anordnung, die mit einem handelsüblichen Thermokopf ausge¬ stattet ist, auf handelsübliches Videoprintpapier (Color Videoprint Paper der Firma Hitachi) verdruckt.The mixture is knife-coated with a 10 μm doctor blade onto a 6 μm thick polyester film, on the back of which a suitable sliding layer is applied, and blown dry with a hair dryer for 1 minute. Before the ribbon can be printed, it must be left to air dry for at least 24 hours, as residual solvents can impair the printing process. The ink ribbons are printed onto commercially available video print paper (color video print paper from Hitachi) on a computer-controlled test arrangement which is equipped with a commercially available thermal head.
Durch Veränderung der Spannung wird die Energieabgabe des Thermokopfs gesteuert, wobei die eingestellte Impulsdauer 7 ms beträgt und immer nur ein Impuls abgegeben wird. Die abgegebene Energie liegt zwischen 0,5 und 2,0 mJ/Dot.The energy output of the thermal head is controlled by changing the voltage, the set pulse duration being 7 ms and only one pulse being output at a time. The energy delivered is between 0.5 and 2.0 mJ / dot.
Da die Höhe der Anfärbung direkt proportional der zugeführten Energie ist, kann ein Farbkeil erzeugt und spektroskopisch ausgewertet werden.Since the amount of staining is directly proportional to the energy supplied, a color wedge can be generated and evaluated spectroscopically.
Aus der graphischen Auftragung der Farbtiefe gegen die zuge¬ führte Energie je Heizelement wird der Q*-Wert (= Energie in mJ für den Extinktionswert 1) und die Steigung m in 1/mJ ermittelt.The Q * value (= energy in mJ for the extinction value 1) and the gradient m in 1 / mJ are determined from the graphical plotting of the color depth against the supplied energy per heating element.
Die erhaltenen Ergebnisse sind zusammen mit den Werten für die Lichtechtheit (LE) in der folgenden Tabelle 5 aufgeführt.The results obtained are shown in Table 5 below along with the light fastness (LE) values.
Als Wert für die Beurteilung der Lichtechtheit ist die Anzahl der Bestrahlungsstunden angegeben, nach der 20 % der ursprünglich vorhandenen Farbstoffmenge zerstört war.The value for the assessment of the light fastness is the number of irradiation hours after which 20% of the amount of dye originally present had been destroyed.
Tabelle 5Table 5
Figure imgf000027_0001
Figure imgf000028_0001
Anwendung beim Färben
Figure imgf000027_0001
Figure imgf000028_0001
Use in dyeing
10 g Polyestergewebe werden bei einer Temperatur von 50°C in 200 ml einer Färbeflotte gegeben, die X Gew. -%, bezogen auf das Polyestergewebe, Farbstoffmischung enthält und deren pH-Wert mittels Essigsäure auf 4,5 eingestellt ist. Man behandelt 5 min bei 50°C, steigert dann die Temperatur der Flotte innerhalb von 30 min auf 130°C, hält 60 min bei dieser Temperatur und läßt dann innerhalb von 20 min auf 60°C abkühlen.10 g of polyester fabric are placed at a temperature of 50 ° C. in 200 ml of a dyeing liquor which contains X% by weight, based on the polyester fabric, of the dye mixture and whose pH is adjusted to 4.5 using acetic acid. It is treated for 5 minutes at 50 ° C., then the temperature of the liquor is raised to 130 ° C. within 30 minutes, kept at this temperature for 60 minutes and then allowed to cool to 60 ° C. within 20 minutes.
Danach wird das ausgefärbte Polyestergewebe reduktiv gereinigt, indem man es 15 min in 200 ml einer Flotte, die 5 ml/1 32 gew. -%ige Natronlauge, 3 g/1 Natriumdithionit und 1 g/1 eines Anlagerungsproduktes von 48 mol Ethylenoxid an 1 mol Ricinusol enthält, bei 65°C behandelt. Schließlich wird das Gewebe gespült, mit verdünnter Essigsäure neutralisiert, nochmals gespült und getrocknet.The dyed-out polyester fabric is then reductively cleaned by placing it in 200 ml of a liquor containing 5 ml / l 32 wt. -% sodium hydroxide solution, 3 g / 1 sodium dithionite and 1 g / 1 of an adduct of 48 mol of ethylene oxide with 1 mol of Ricinusol, treated at 65 ° C. Finally, the tissue is rinsed, neutralized with dilute acetic acid, rinsed again and dried.
Die Farbstoffmischungen Nr. 41, 42 und 43 wurden jeweils in einer Menge (X) von 0,35 Gew. -% angewandt. Man erhielt hochbrillante rote Färbungen mit hervorragender Lichtechtheit.Dye mixtures Nos. 41, 42 and 43 were each used in an amount (X) of 0.35% by weight. Highly brilliant red dyeings with excellent lightfastness were obtained.
Ferner wurden die Farbstoffe Nr. 22 und 28 im Massenverhältnis 1:1, 1:2 und 1:3 gemischt und die Mischungen jeweils in einer Menge (X) von 0,35 Gew. -% angewandt. Man erhielt ebenfalls hoch¬ brillante Färbungen mit hervorragender Lichtechtheit. Dyes Nos. 22 and 28 were further mixed in a mass ratio of 1: 1, 1: 2 and 1: 3, and the mixtures were each used in an amount (X) of 0.35% by weight. Highly brilliant dyeings with excellent lightfastness were also obtained.

Claims

Patentansprüche claims
1. Farbstoffmischungen, enthaltend mindestens einen Pyridon- farbstoff der Formel I,1. dye mixtures containing at least one pyridone dye of the formula I,
Figure imgf000030_0001
Figure imgf000030_0001
in derin the
X1 einen 5- oder 6-gliedrigen carbocyclischen oder heterocyclischen Rest,X 1 is a 5- or 6-membered carbocyclic or heterocyclic radical,
X2 Cyano, Carbamoyl, Ci -C6-Alkoxycarbonyl, Carboxyl oder Cι-C4-Alkanoyl undX 2 cyano, carbamoyl, Ci -C 6 alkoxycarbonyl, carboxyl or -C-C 4 alkanoyl and
X3 C1-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unter¬ brochen sein kann, gegebenenfalls substituiertes Phenyl oder einen Rest der Formel NE^-E2, wobei E1 und E2 unabhängig voneinander jeweils für Wasser¬ stoff, C1-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Ether¬ funktion unterbrochen sein kann, C5-C7-Cycloalkyl, gegebenenfalls substituiertes Phenyl, gegebenenfalls substituiertes Pyridyl, gegebenenfalls substituiertes Cι-Ci3-Alkanoyl, Cι-Ci3-Alkoxycarbonyl, gegebenenfalls substituiertes Cι-C13-Alkylsulfonyl, C5-C7-Cycloalkyl- sulfonyl, gegebenenfalls substituiertes Phenylsul- fonyl, gegebenenfalls substituiertes Pyridylsulfonyl, gegebenenfalls substituiertes Benzoyl, Pyridylcar- bonyl oder Thienylcarbonyl oder E1 und E2 zusammen mit dem sie verbindenden Stickstoffatom gegebenen¬ falls durch Cι~C4-Alkyl substituiertes Succinimido, gegebenenfalls durch Cι~C4-Alkyl substituiertesX 3 C 1 -C 13 alkyl, which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, optionally substituted phenyl or a radical of the formula NE ^ -E 2 , where E 1 and E 2 independently of one another in each case for hydrogen, C 1 -C 13 -alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, C 5 -C 7 -cycloalkyl, optionally substituted phenyl, optionally substituted pyridyl, optionally substituted C 1 -C 3 alkanoyl, C 1 -C 3 alkoxycarbonyl, optionally substituted C 1 -C 13 alkylsulfonyl, C 5 -C 7 cycloalkylsulfonyl, optionally substituted phenylsulfonyl, optionally substituted pyridylsulfonyl, optionally substituted benzoyl, pyridylcarbonyl or Thienylcarbonyl or E 1 and E 2 together with the nitrogen atom connecting them, optionally substituted by C 1 -C 4 -alkyl, optionally by succinimido Cι ~ C 4 alkyl substituted
Phthalimido oder einen 5- oder 6-gliedrigen gesät¬ tigten heterocyclischen Rest, der gegebenenfalls weitere Heteroatome enthält, stehen, bedeuten, sowie mindestens einen Azofarbstoff der Formel IIAre phthalimido or a 5- or 6-membered saturated heterocyclic radical which optionally contains further heteroatoms, and at least one azo dye of the formula II
Figure imgf000031_0001
Figure imgf000031_0001
in derin the
R^R2 und R3 unabhängig voneinander jeweils Wasserstoff,R ^ R 2 and R 3 are each independently hydrogen,
C1-C13-Alkyl, das gegebenenfalls substituiert ist und durch 1 bis 3 Sauerstoffatome in Etherfunktion unterbrochen sein kann, substituiertes Phenyl oder gegebenenfalls substituiertes C3-C7-Cycloalkyl,C 1 -C 13 alkyl which is optionally substituted and can be interrupted by 1 to 3 oxygen atoms in ether function, substituted phenyl or optionally substituted C 3 -C 7 cycloalkyl,
R4 Cι-C4-Alkyl,R4 -CC 4 alkyl,
R5 Cyano, Carbamoyl, Ci-Cg-Alkoxycarbonyl, Carboxyl oder Cι-C4-Alkanoyl undR5 cyano, carbamoyl, Ci-Cg-alkoxycarbonyl, carboxyl or -C-C 4 alkanoyl and
den Rest einer Diazokomponente bedeuten,represent the rest of a diazo component,
und/oder einen Anthrachinonfarbstoff der Formel IIIand / or an anthraquinone dye of the formula III
Figure imgf000031_0002
Figure imgf000031_0002
in derin the
L1 Wasserstoff, Ci-Cio-Alkyl oder gegebenenfalls substi¬ tuiertes Phenyl,L 1 is hydrogen, Ci-Cio-alkyl or optionally substituted phenyl,
L2 und L3 unabhängig voneinander jeweils Wasserstoff, Cι-Cιo-Alkoxy, Benzyloxy, Ci-C4-Alkylbenzyloxy, 2-Phenylethoxy, 2- (Cι-C4-Alkylphenyl) ethoxy, Cι-Cιo-Alkylthio, Benzylthio, 2-Phenylethylthio, Halogen, Hydroxyphenyl, Cι-C4-Alkoxyphenyl oder einen Rest der FormelL 2 and L 3 each independently of one another are hydrogen, C 1 -C 8 -alkoxy, benzyloxy, C 1 -C 4 -alkylbenzyloxy, 2-phenylethoxy, 2- (C 1 -C 4 -alkylphenyl) ethoxy, C 1 -C 8 -alkylthio, benzylthio, 2 -Phenylethylthio, Halogen, hydroxyphenyl, -CC 4 alkoxyphenyl or a radical of the formula
Figure imgf000032_0001
Figure imgf000032_0001
worin G1 für Sauerstoff oder Schwefel und G2 für Wasserstoff oder Ci-Cß-Monoalkylsulfamoyl, dessen Alkylkette durch 1 oder 2 Sauerstoffatome in Ether¬ funktion unterbrochen sein kann, stehen, undwherein G 1 represents oxygen or sulfur and G 2 represents hydrogen or Ci-C ß -monoalkylsulfamoyl, the alkyl chain of which can be interrupted by 1 or 2 oxygen atoms in ether function, and
L4 Amino, Hydroxy oder gegebenenfalls durch Phenyl sub¬ stituiertes Ci-Cio-Alkylthio bedeuten.L 4 is amino, hydroxy or optionally substituted by phenyl Ci-Cio-alkylthio.
2. Farbstoffmischungen nach Anspruch 1, enthaltend einen oder mehrere Pyridonfarbstoffe der Formel I, in der X2 Cyano bedeutet.2. dye mixtures according to claim 1, containing one or more pyridone dyes of the formula I in which X 2 is cyano.
3. Farbstoffmischungen nach Anspruch 1, enthaltend einen oder mehrere Pyridonfarbstoffe der Formel I, in der X3 C1-C13-Alkyl, das gegebenenfalls durch 1 bis 3 Sauerstoff- atome in Etherfunktion unterbrochen ist, bedeutet.3. dye mixtures according to claim 1, containing one or more pyridone dyes of the formula I in which X 3 is C 1 -C 13 alkyl, which is optionally interrupted by 1 to 3 oxygen atoms in ether function.
4. Farbstoffmischungen nach Anspruch 1, enthaltend einen oder mehrere Pyridonfarbstoffe der Formel I, in der X1 einen Rest bedeutet, der sich von einer Komponente aus der Benzol-, Indol-, Chinolin-, Naphthalin-, Pyrrol-, Thiazol-, Benz- imidazol-, Benzthiazol- , Thiophen- oder Pyridinreihe ab- leitet.4. dye mixtures according to claim 1, containing one or more pyridone dyes of the formula I in which X 1 is a radical which is derived from a component of the benzene, indole, quinoline, naphthalene, pyrrole, thiazole, benz - Derives imidazole, benzothiazole, thiophene or pyridine series.
5. Farbstoffmischungen nach Anspruch 1, enthaltend einen oder mehrere Azofarbstoffe der Formel II, in der D sich von einer Diazokomponente aus der Anilin-, Phenylazoanilin- , Amino- thiophen-, Phenylazoaminothiophen- , Aminothiazol- , Phenyl- azoaminothiazol- , Aminoisothiazol- oder Aminothiadiazolreihe ableitet. 5. dye mixtures according to claim 1, containing one or more azo dyes of the formula II, in which D is a diazo component from the aniline, phenylazoaniline, aminothiophene, phenylazoaminothiophene, aminothiazole, phenyl azoaminothiazole, aminoisothiazole or Aminothiadiazole series derived.
6. Färbstoffmischungen nach Anspruch 1, enthaltend einen oder mehrere Anthrachinonfarbstoffe der Formel lila6. dye mixtures according to claim 1, containing one or more anthraquinone dyes of the formula purple
Figure imgf000033_0001
Figure imgf000033_0001
in der G1 und G2 jeweils die in Anspruch 1 genannte Bedeutung besitzen.in which G 1 and G 2 each have the meaning given in Claim 1.
7. Farbstoffmischungen nach Anspruch 1, enthaltend 20 bis 80 Gew.%, bezogen auf das Gewicht der Farbstoffmischung, einen oder mehrere Pyridonfarbstoffe der Formel I sowie 20 bis 80 Gew.%, bezogen auf das Gewicht der Farbstoffmischung, einen oder mehrere Azofarbstoffe der Formel II und/oder Anthrachinonfarbstoffe der Formel III.7. dye mixtures according to claim 1, containing 20 to 80 wt.%, Based on the weight of the dye mixture, one or more pyridone dyes of the formula I and 20 to 80 wt.%, Based on the weight of the dye mixture, one or more azo dyes of the formula II and / or anthraquinone dyes of the formula III.
8. Verfahren zur Übertragung von Farbstoffen von einem Träger auf ein mit Kunststoff beschichtetes Papier durch Diffusion oder Sublimation mit Hilfe einer Energiequelle, dadurch gekennzeichnet, daß man einen Träger verwendet, auf dem sich eine Farbstoffmischung gemäß Anspruch 1 befindet.8. A method for transferring dyes from a support to a plastic-coated paper by diffusion or sublimation using an energy source, characterized in that one uses a support on which there is a dye mixture according to claim 1.
9. Verfahren zum Färben oder Bedrucken von synthetischen Materialien, dadurch gekennzeichnet, daß man die syn¬ thetischen Materialien mit einer Farbstoffmischung gemäß Anspruch 1 behandelt. 9. A method for dyeing or printing synthetic materials, characterized in that the synthetic materials are treated with a dye mixture according to claim 1.
PCT/EP1997/002817 1996-06-12 1997-05-30 Dye mixtures WO1997047690A1 (en)

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GB2335924A (en) * 1998-03-31 1999-10-06 Zeneca Ltd Dyes and ink jet inks based on 5-([N-substituted-aminoaryl]azo)-4-cyanoisothiazole derivatives
US6187084B1 (en) 1998-03-31 2001-02-13 Zeneca Ltd. Ink compositions
GB2335924B (en) * 1998-03-31 2003-09-03 Zeneca Ltd Dyes and ink compositions comprising 5-azo-isothiazole derivatives
JP2019056116A (en) * 2014-02-19 2019-04-11 キヤノン株式会社 Aqueous ink composition
JP2019521195A (en) * 2016-05-25 2019-07-25 ハンツマン アドバンスト マテリアルズ （スイッツァランド） ゲーエムベーハーＨｕｎｔｓｍａｎ Ａｄｖａｎｃｅｄ Ｍａｔｅｒｉａｌｓ （Ｓｗｉｔｚｅｒｌａｎｄ） Ｇｍｂｈ Dispersed azo dyes, process for their preparation and their use

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ID17442A (en) 1997-12-24

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