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.

Landscapes

• 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)
• Coloring (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=7796723

Family Applications (1)

Country Status (3)

Cited By (3)

Families Citing this family (5)

Citations (6)

• 1996
  • 1996-06-12 DE DE1996123411 patent/DE19623411A1/de not_active Withdrawn
• 1997
  • 1997-05-30 WO PCT/EP1997/002817 patent/WO1997047690A1/de active Application Filing
  • 1997-06-10 ID IDP971989A patent/ID17442A/id unknown

Patent Citations (7)

Also Published As

Similar Documents

Legal Events