EP0439200B1 - Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos - Google Patents

Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos Download PDF

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Publication number
EP0439200B1
EP0439200B1 EP91101566A EP91101566A EP0439200B1 EP 0439200 B1 EP0439200 B1 EP 0439200B1 EP 91101566 A EP91101566 A EP 91101566A EP 91101566 A EP91101566 A EP 91101566A EP 0439200 B1 EP0439200 B1 EP 0439200B1
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EP
European Patent Office
Prior art keywords
alkyl
cyano
sulfyl
dyes
und
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Expired - Lifetime
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EP91101566A
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German (de)
English (en)
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EP0439200A1 (fr
Inventor
Volker Dr. Bach
Karl-Heinz Dr. Etzbach
Ruediger Dr. Sens
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BASF SE
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BASF SE
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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382Contact thermal transfer or sublimation processes
    • B41M5/385Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/3854Dyes containing one or more acyclic carbon-to-carbon double bonds, e.g., di- or tri-cyanovinyl, methine
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/913Material designed to be responsive to temperature, light, moisture
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/914Transfer or decalcomania

Definitions

  • the present invention relates to a new method for transferring bichromophoric cyano group-containing methine dyes, which have two individual chromophores which are connected to one another via a bridge member, from a support to paper coated with plastic with the aid of an energy source.
  • a transfer sheet which contains a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries, on a support, with an energy source, e.g. with a heating head, heated by short heating impulses (duration: fractions of a second) from the back, whereby the dye migrates from the transfer sheet and diffuses into the surface coating of a recording medium.
  • an energy source e.g. with a heating head
  • short heating impulses duration: fractions of a second
  • Suitable radicals R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl , Hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl or isooctyl.
  • R 1 and R 5 are, for example, nonyl, isononyl, decyl, isodecyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-butoxyethyl, 2-or 3-methoxypropyl, 2-or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2-or 3-butoxypropyl, 4-methoxybutyl, 4-ethoxybutyl, 4-butoxybutyl, 2-cyanoethyl, 3-cyanopropyl, 4-cyanobutyl, 2-hydroxyethyl,
  • R 4 radicals are furthermore, for example, phenyl, 2-, 3- or 4-methylphenyl, 2- or 4-isopropylphenyl, 2-butylphenyl, 2-, 3- or 4-methoxyphenyl, 2-propoxyphenyl, 4-butoxyphenyl, 2- ( But-2-oxy) phenyl, benzyl, 2-, 3- or 4-methylbenzyl, 2-, 3- or 4-methoxybenzyl, fluorine, chlorine, bromine, thien-2-yl or thien-3-yl.
  • R 2 and R 3 are furthermore methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, formylamino, acetylamino, propionylamino, butyrylamino, methylsulfonylamino, ethylsulfonylamino-isyl-sulfonamyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sulfyl-sul
  • Residues X are e.g. Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, 2-methoxyethoxycarbonyl, methylcarbamoyl, ethylcarbamoyl, 2-methoxyethylcarbamoyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, cyclopentylcarbamoyloyl cyclohexylcarbamylloyl cyclohexylcarbamoyl cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoyl, cyclohexylcarbamoy
  • Residues E 1 and E 2 are, for example, methylene, 1,2-ethylene, ethylidene, 1,2- or 1,3-propylene or 1,4-, 1,3- or 2,3-butylene.
  • Residues D are, for example -O- (CH 2 ) 2 -O-, -O- (CH 2 ) 3 -O-, -O- (CH 2 ) 4 -O-, -O- (CH 2 ) 5 -O-, -O - (CH 2 ) 6 -O-, -O- (CH 2 ) 7 -O-, -O- (CH 2 ) 8 -O-, -O- (CH 2 ) 9 -O-, -O- ( CH 2 ) 10 -O-,
  • bichromophoric methine dyes used in the process according to the invention are generally known and are e.g. in GB-A-1 201 925, US-A-3 553 245, DE-A-1 569 678, DE-A-2 519 592, DE-A-3 020 473, WO-A-86/04904 or WO-A-87/01121 described or can be obtained by the methods mentioned there.
  • the dyes transferred in the process according to the invention are generally distinguished by improved fixation in the recording medium at room temperature, easier thermal transferability, higher lightfastness, higher stability to moisture and chemical substances, better solubility in organic solvents, higher Ribbon stability and higher color purity.
  • the dyes of the formula I used in the new process are advantageously suitable for producing a trichromatic system required for the subtractive color mixture.
  • the good transferability allows a large variation of the plastics used as a receiver and thus a very good adaptation of the dyes to the overall system (donor / receiver).
  • the dyes are processed to 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 printing ink in 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 support using a doctor blade and the dyeing can be dried in air.
  • Suitable organic solvents for the dyes I are, for example, those in which the solubility of the dyes I 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.
  • binders All resins or polymer materials which are soluble in organic solvents and are capable of binding the dye to the inert support in an abrasion-resistant manner are suitable as binders. Preference is given to binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film without the dye crystallizing out visibly.
  • binders examples include cellulose derivatives, e.g. Methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyd resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
  • Polymers and copolymers of acrylates or their derivatives, such as polyacrylic acid, polymethyl methacrylate or styrene-acrylate copolymers, polyester resin, polyamide resin, polyurethane resin or natural CH resin, such as gum arabic are also suitable as binders.
  • Other suitable binders are e.g. in DE-A-3 524 519.
  • Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyrate or polyvinyl acetate.
  • the weight ratio of binder: dye is generally 1: 1 to 10: 1.
  • Inert carriers are, for example, tissue paper, blotting paper or glassine paper or plastic films with good heat resistance, for example metal-coated polyester, polyamide or polyimide.
  • the inert carrier is optionally additionally coated on the side facing the thermal head with a lubricating layer (slipping layer) in order to prevent the thermal head from sticking to the carrier material. Suitable lubricants are described, for example, in EP-A-216 483 or EP-A-227 095.
  • the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
  • all temperature-stable plastic layers with affinity for the dyes to be transferred can be used as the dye-receiving layer, e.g. modified polycarbonate or polyester.
  • Suitable formulations for the receiver layer composition are e.g. in EP-A-227 094, EP-A-133 012, EP-A-133 011, EP-A-111 004, JP-A-199 997/1986, JP-A-283 595/1986, JP- A-237 694/1986 or JP-A-127 392/1986 described in detail.
  • the transmission takes place by means of an energy source, e.g. by means of a laser or by means of a thermal head which must 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 ms.
  • the dye migrates from the transfer sheet and diffuses into the surface coating of the recording medium.
  • the dyes listed in the following tables were processed according to ⁇ ) and the resulting dye-coated supports were tested for transfer behavior according to ⁇ ).
  • the tables show the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride), the binders used and the weight ratio of dye: binder: auxiliaries.
  • the following methine dyes can be transferred in an analogous manner.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Claims (2)

  1. Procédé de transfert de colorants méthiniques bichromophores entre un support et un papier revêtu de matière plastique à l'aide d'une source d'énergie, caractérisé en ce que l'on utilise un support sur lequel se trouvent un ou plusieurs colorants de formule I
    Figure imgb0025
    dans laquelle
    L   est mis pour un maillon de pontage qui ne permet pas de conjugaison d'électrons π entre les restes Z et Y,
    X   sont semblables ou différents et sont mis chacun pour un reste cyano, (alcoxy en C1-C6)carbonyle ou mono(alkyl en C1-C6)carbamoyle, les groupements alkyle pouvant être interrompus chacun par 1 ou 2 atomes d'oxygène, pour un reste (cycloalcoxy en C5-C7)carbonyle, mono(cycloalkyl en C5-C7)carbamoyle, phénoxycarbonyle ou monophénylcarbamoyle et
    Z et Y   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, en combinaison avec le maillon de pontage L, pour un reste de formule
    Figure imgb0026
    n   est égal à 0 ou 1,
    R1 et R5   sont identiques ou différents et sont mis chacun, indépendamment l'un de l'autre, pour un reste alkyle, alcoxyalkyle, alcoxycarbonylalkyle ou alcanoyloxyalkyle, ces restes renfermant chacun jusqu'à 10 atomes de carbone et pouvant être éventuellement substitués par un groupement hydroxy ou cyano, pour un atome d'hydrogène ou pour un reste benzyle, cyclohexyle, phényle ou tolyle,
    R2 et R3   sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un reste alkyle en C1-C8, alcoxy en C1-C6, alcanoylamino en C1-C6 ou alkylsulfonylamino en C1-C6,
    R4   est mis pour un atome d'hydrogène, d'halogène ou pour un reste alkyle en C1-C8, phényle éventuellement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4, pour un reste benzyle éventuellement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4, pour un reste cyclohexyle, thiényle ou pour le reste -NHR1, R1 ayant la signification donnée ci-dessus, et
    R6   représente un atome d'hydrogène ou un reste alkyle en C1-C8.
  2. Procédé selon la revendication 1, caractérisé en ce que X représente un reste cyano.
EP91101566A 1990-02-15 1991-02-06 Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos Expired - Lifetime EP0439200B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4004614A DE4004614A1 (de) 1990-02-15 1990-02-15 Verfahren zur uebertragung von bichromophoren cyanogruppen enthaltenden methinfarbstoffen
DE4004614 1990-02-15

Publications (2)

Publication Number Publication Date
EP0439200A1 EP0439200A1 (fr) 1991-07-31
EP0439200B1 true EP0439200B1 (fr) 1996-08-14

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EP91101566A Expired - Lifetime EP0439200B1 (fr) 1990-02-15 1991-02-06 Procédé pour le transfert des colorants méthiniques bichromophores contenant des groupes cyanos

Country Status (4)

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US (1) US5139997A (fr)
EP (1) EP0439200B1 (fr)
JP (1) JPH05318938A (fr)
DE (2) DE4004614A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4105197A1 (de) * 1991-02-20 1992-08-27 Basf Ag Bichromophore methinfarbstoffe
PL348193A1 (en) 1998-12-11 2002-05-06 Pharmasolutions Self-emulsifying compositions for drugs poorly soluble in water
US6057289A (en) * 1999-04-30 2000-05-02 Pharmasolutions, Inc. Pharmaceutical composition comprising cyclosporin in association with a carrier in a self-emulsifying drug delivery system
DE10009580A1 (de) * 2000-02-29 2001-08-30 Bayer Ag Verfahren zum Massefärben von Kunststoffen
US6841514B2 (en) * 2002-12-26 2005-01-11 Eastman Kodak Company Thermal transfer imaging element containing infrared bichromophoric colorant
US6831163B2 (en) * 2002-12-26 2004-12-14 Eastman Kodak Company Bichromophoric molecules
US7288121B2 (en) * 2004-02-27 2007-10-30 L'oreal S.A. Composition comprising at least one mixed dye comprising at least one chromophore chosen from compounds of the methine family and/or the carbonyl family, dyeing process and kit, and mixed dyes
US7303591B2 (en) * 2004-02-27 2007-12-04 L'oreal S.A. Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes
FR2879927A1 (fr) * 2004-02-27 2006-06-30 Oreal Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre (hetero) aromatique,procede de coloration et colorants mixtes.
FR2866808A1 (fr) * 2004-02-27 2005-09-02 Oreal Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre(herero)aromatique ou azine cyclique, procede de coloration et colorants mixtes
FR2866803B1 (fr) * 2004-02-27 2007-06-29 Oreal Composition comprenant un colorant mixte a base d'au moins un chromophore de type nitre (hetero) aromatique ou azine cyclique, procede de coloration et colorants mixtes
FR2889954B1 (fr) * 2005-08-26 2007-10-19 Oreal Colorants mixtes cationiques comprenant un chromophore anthraquinone et leur utilisation en colorant capillaire

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3846069A (en) * 1968-07-26 1974-11-05 Ciba Geigy Ag Sublimation transfer dyeing with styryl dyes
CH1123568A4 (de) * 1968-07-26 1972-02-29 Ciba Geigy Ag Transferdruckverfahren auf Textilmaterialien
US4018810A (en) * 1972-10-25 1977-04-19 Minnesota Mining And Manufacturing Company Organic dye having fluoroaliphatic substituent
US4748149A (en) * 1987-02-13 1988-05-31 Eastman Kodak Company Thermal print element comprising a yellow merocyanine dye stabilized with a cyan indoaniline dye
US4833123A (en) * 1987-10-08 1989-05-23 Sumitomo Chemical Company Limited Yellow dye-donor element used in thermal transfer and thermal transfer and thermal transfer sheet using it

Also Published As

Publication number Publication date
DE4004614A1 (de) 1991-08-22
JPH05318938A (ja) 1993-12-03
US5139997A (en) 1992-08-18
EP0439200A1 (fr) 1991-07-31
DE59108061D1 (de) 1996-09-19

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