EP0479076B1 - Procédé pour le transfert des colorants indoanilines - Google Patents

Procédé pour le transfert des colorants indoanilines Download PDF

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Publication number
EP0479076B1
EP0479076B1 EP91116088A EP91116088A EP0479076B1 EP 0479076 B1 EP0479076 B1 EP 0479076B1 EP 91116088 A EP91116088 A EP 91116088A EP 91116088 A EP91116088 A EP 91116088A EP 0479076 B1 EP0479076 B1 EP 0479076B1
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Prior art keywords
transfer
dyes
hydrogen
methyl
und
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EP91116088A
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German (de)
English (en)
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EP0479076A1 (fr
Inventor
Volker Dr. Bach
Ruediger Dr. Sens
Karl-Heinz Dr. Etzbach
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BASF SE
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BASF SE
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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
    • B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • Y—GENERAL 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
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania

Definitions

  • the present invention relates to a new method for transferring indoaniline dyes from a support to a plastic-coated paper using 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 or a laser, 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 or a laser
  • short heating impulses duration: fractions of a second
  • the color recording is carried out using the three subtractive primary colors yellow, magenta, cyan (and possibly black).
  • JP-A-219 693/1990, JP-A-84 388/1990 and EP-A-366 963 also describe the use of indoaniline dyes with an aniline residue in thermal transfer processes.
  • EP-A-415 203 which applies to the designated contracting states as state of the art according to Art. 54 (3), EPC, includes Indoaniline dyes with a thiazole residue and a method for their thermal transfer are known.
  • substituted alkyl groups appear in the above formula II, e.g. Cyano, phenyl, tolyl, hydroxy, C1-C6-alkanoyloxy, C1-C4-alkoxycarbonyl or C1-C4-alkoxycarbonyloxy, in which case the alkoxy group may be substituted by phenyl or C1-C4-alkoxy.
  • Suitable radicals R2, R5 and R7 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
  • R5 and R7 are still e.g. Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, 2-methoxyethyl, 2- or 3-methoxypropyl, 2-ethoxyethyl, 2- or 3-ethoxypropyl, 2-propoxyethyl, 2- or 3-propoxypropyl, 2-butoxyethyl, 2- or 3-butoxypropyl, 3,6-dioxaheptyl or 3,6-dioxaoctyl.
  • Residues R5 are still e.g. 2-cyanoethyl, 2- or 3-cyanopropyl, 2-acetyloxyethyl, 2- or 3-acetyloxypropyl, 2-isobutyryloxyethyl, 2- or 3-isobutyryloxypropyl, 2-methoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2-ethoxycarbonylethyl, 2- or 3-ethoxycarbonylpropyl 2-methoxycarbonyloxyethyl, 2- or 3-methoxycarbonyloxypropyl, 2-ethoxycarbonyloxyethyl, 2- or 3-ethoxycarbonyloxypropyl, 2-butoxycarbonyloxyethyl, 2- or 3-butoxycarbonyloxypropyl, 2- (2-phenylethoxycarbonyloxy) ethyl, 2- or 3 - (2-Phenylethoxycarbonyloxy) propyl, 2- (2-ethoxyeth
  • R4 are e.g. Mono- or dimethylaminosulfonylamino, mono- or diethylaminosulfonylamino, mono- or dipropylaminosulfonylamino, mono- or diisopropylaminosulfonylamino, mono- or dibutylaminosulfonylamino, (N-methyl-N-ethylaminosulfonyl) amino, methylsulfonylamylamylamylamylamylamylylylamino, ethylsulfonylamino, ethylsulfonylamino, ethylsulfonylamino, ethylsulfonylamino,
  • a procedure is particularly preferred in which a support is used on which there are one or more dyes of the formula I in which R 1 and R 2 are each hydrogen or methyl and R 3 and X are each chlorine.
  • indoaniline dyes of the formula I can be prepared by methods known per se, as described, for example, in the earlier patent applications EP-A-416 434 and EP-A-0 449 109, which belong to the prior art according to Art. 54 (3) EPC , getting produced.
  • the dyes of the formula I which are transferred in the process according to the invention are generally distinguished by improved migration properties in the recording medium at room temperature, easier thermal transferability, higher thermal and photochemical stability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength, better solubility or better suitability for subtractive color mixing (higher color purity, more favorable form of the absorption band, eg narrow half-width or greater flank steepness on the short-wave side). They are also particularly advantageous for dye mixtures with triazolopyridine dyes, as described in the earlier patent application EP-A-416 434. This applies mainly with regard to better transferability, higher ribbon stability (better compatibility with the binder), higher lightfastness, better distribution of the transfer dyes in the recording medium and in particular for the production of better black mixtures.
  • the dyes 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 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.
  • 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 those binders which, after the printing ink has dried in air, absorb the dye in the form of a clear, transparent film, without any visible crystallization of the dye occurring.
  • 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 cellulose derivatives or polyvinyl butyrate.
  • the weight ratio of binder: dye is generally 1: 1 to 5: 1.
  • auxiliaries examples include release agents such as those mentioned in EP-A-227 092, EP-A-192 435 or the patent applications cited therein.
  • organic additives which prevent the transfer dyes from crystallizing out during storage or when the ribbon is heated, for example cholesterol or vanillin.
  • Inert carriers are e.g. Silk, blotting or glassine paper or plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
  • the inert carrier is optionally additionally coated with a slip layer on the side facing the energy source in order to prevent the energy source, in particular the thermal head, from sticking to the carrier material.
  • Suitable lubricants are e.g. in EP-A-216 483 or EP-A-227 095.
  • the thickness of the dye carrier is generally 3 to 30 »m, preferably 5 to 10» m.
  • 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, the latter having to be heatable 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.

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

Claims (3)

  1. Procédé de transfert de colorants de l'indoaniline entre un support et un papier enduit de matière plastique, par diffusion ou sublimation 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 imgb0013
     dans laquelle
    R¹, R² et R³   sont identiques ou différents et représentent chacun, indépendamment les uns des autres, un atome d'hydrogène, un reste méthyle ou un atome de fluor ou de chlore,
    X   représente un atome de fluor ou de chlore et
    K   représente un reste de formule II
    Figure imgb0014
     dans laquelle
    R⁴   est mis pour un atome d'hydrogène, pour un groupement méthyle, méthoxy, mono- ou di(alkyl en C₁-C₄)aminosulfonylamino, (alkyl en C₁-C₄)sulfonylamino ou pour le reste -NHCOR⁷ ou -NHCO₂R⁷, R⁷ représentant un reste phényle, benzyle, tolyle ou alkyle en C₁-C₈ qui est éventuellement interrompu par un ou deux atomes d'oxygène en fonction éther,
    R⁵   est mis pour un atome d'hydrogène, pour un reste alkyle en C₁-C₈ qui est éventuellement substitué et peut être interrompu par un ou deux atomes d'oxygène en fonction éther, ou pour un reste cyoloalkyle en C₅-C₇, et
    R⁶   est mis pour un atome d'hydrogène ou pour un reste méthyle ou méthoxy.
  2. Procédé selon la revendication 1, caractérisé en ce que l'on utilise un support sur lequel se trouvent un ou plusieurs colorants de formule III
    Figure imgb0015
     dans laquelle
    R⁴   représente un atome d'hydrogène ou un reste méthyle ou acétylamino,
    R⁵   représente un atome d'hydrogène, un resta alkyle en C₁-C₆ qui est éventuellement substitué et peut être interrompu par un ou deux atomes d'oxygène en fonction éther, ou un reste cycloalkyle en C₅-C₇,
    R⁶   représente un atome d'hydrogène et
    R¹, R², R³ et X   ont chacun la signification donnée dans la revendication 1.
  3. Procédé selon la revendication 1, caractérisé en ce que l'on utilise un support sur lequel se trouvent un ou plusieurs colorants de formule I, dans laquelle R¹ et R² représentent chacun un atome d'hydrogène ou un reste méthyle et R³ et X représentent chacun un atome de chlore.
EP91116088A 1990-10-04 1991-09-21 Procédé pour le transfert des colorants indoanilines Expired - Lifetime EP0479076B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4031255A DE4031255A1 (de) 1990-10-04 1990-10-04 Verfahren zur uebertragung von indoanilinfarbstoffen
DE4031255 1990-10-04

Publications (2)

Publication Number Publication Date
EP0479076A1 EP0479076A1 (fr) 1992-04-08
EP0479076B1 true EP0479076B1 (fr) 1995-07-26

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EP91116088A Expired - Lifetime EP0479076B1 (fr) 1990-10-04 1991-09-21 Procédé pour le transfert des colorants indoanilines

Country Status (4)

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US (1) US5221658A (fr)
EP (1) EP0479076B1 (fr)
JP (1) JP3171884B2 (fr)
DE (2) DE4031255A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4218359A1 (de) * 1992-06-04 1993-12-09 Basf Ag Polymerisate, die Methin- oder Azamethinfarbstoffe enthalten
DE69307042T2 (de) * 1992-07-14 1997-06-26 Agfa Gevaert Nv Farbstoffdonorelement zur Anwendung in der thermischen Farbstoffsublimationsübertragung
ATE147017T1 (de) * 1992-07-14 1997-01-15 Agfa Gevaert Nv Schwarzgefärbte farbstoffmischung zur anwendung in der thermischen farbstoffsublimationsübertragung
US5735892A (en) * 1993-08-18 1998-04-07 W. L. Gore & Associates, Inc. Intraluminal stent graft
DE4440486A1 (de) * 1994-11-12 1996-05-15 Basf Ag Azamethinfarbstoffe
FR3052969B1 (fr) * 2016-06-23 2020-02-21 L'oreal Utilisation pour la coloration des fibres keratiniques d’un compose de type azomethinique a motif derive de quinoline

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59182839A (ja) * 1983-04-01 1984-10-17 Konishiroku Photo Ind Co Ltd 着色樹脂組成物
JPH0717107B2 (ja) * 1985-05-23 1995-03-01 大日本印刷株式会社 熱転写シ−ト
JPH07115546B2 (ja) * 1988-03-30 1995-12-13 三菱化学株式会社 感熱転写シート
US4857503A (en) * 1988-05-13 1989-08-15 Minnesota Mining And Manufacturing Company Thermal dye transfer materials
JPH0284388A (ja) * 1988-09-21 1990-03-26 Hitachi Ltd 熱転写シート
JPH0794185B2 (ja) * 1988-10-05 1995-10-11 富士写真フイルム株式会社 感熱転写材料
JPH02219693A (ja) * 1989-02-22 1990-09-03 Mitsubishi Kasei Corp 感熱転写シート及び感熱転写シート用インキ組成物
DE3928243A1 (de) * 1989-08-26 1991-02-28 Basf Ag Merocyaninartige thiazolfarbstoffe sowie ein verfahren zum thermischen transfer dieser farbstoffe
DE3929698A1 (de) * 1989-09-07 1991-03-14 Basf Ag Triazolopyridinfarbstoffe sowie ein verfahren zum thermischen transfer von methinfarbstoffen

Also Published As

Publication number Publication date
EP0479076A1 (fr) 1992-04-08
JP3171884B2 (ja) 2001-06-04
DE4031255A1 (de) 1992-04-09
US5221658A (en) 1993-06-22
JPH04234694A (ja) 1992-08-24
DE59106079D1 (de) 1995-08-31

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