EP0509302B1 - Procédé pour le transfert de colorants méthiniques - Google Patents

Procédé pour le transfert de colorants méthiniques Download PDF

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Publication number
EP0509302B1
EP0509302B1 EP92105403A EP92105403A EP0509302B1 EP 0509302 B1 EP0509302 B1 EP 0509302B1 EP 92105403 A EP92105403 A EP 92105403A EP 92105403 A EP92105403 A EP 92105403A EP 0509302 B1 EP0509302 B1 EP 0509302B1
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Prior art keywords
alkyl
mono
alkoxy
substituted
formula
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German (de)
English (en)
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EP0509302A1 (fr
Inventor
Karl-Heinz Dr. Etzbach
Ruediger Dr. Sens
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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
    • 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 methine 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-229 786/1985, JP-A-84 390/1990 and in EP-A-258 856 aniline derivatives for this purpose which have the tricyanovinyl radical in the para position to the amino group.
  • JP-A-32 164/1990 describes dyes which have 4-nitrophenylacetonitrile as a CH-acidic component.
  • EP-A-279 467 describes the transfer of dyes whose CH-acidic components are benzoylacetonitrile and its halogenated derivatives.
  • substituted alkyl or phenyl groups occur in the formulas mentioned above, these are generally mono- to trisubstituted.
  • the substituents can be, for example, cyano, phenyl, tolyl, C 1 -C 6 alkanoyloxy, C 1 -C 4 alkoxycarbonyl or C 1 -C 4 alkoxycarbonyloxy, in the latter case the alkoxy group may be substituted by phenyl, tolyl or C 1 -C 4 alkoxy.
  • Suitable radicals X 2 , X 4 , X 5 , R 3 , R 4 , R 6 and R 8 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
  • R 3 , R 4 and R 6 are furthermore, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl or 2-methylpentyl.
  • R 3 and R 4 are furthermore, for example, 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, 3,6-dioxaoctyl, 2-cyanoethyl, 2- or 3-cyanopropyl, 2-acetyloxyethyl, 2- or 3-acetyloxypropyl, 2-isobutyryloxyethyl, 2- or 2-isobutyryloxypropyl, 2-methoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2-ethoxycarbonylethyl, 2- or 3-ethoxycarbonylpropyl 2-methoxycarbonyloxy
  • Residues X 2 and R 8 are furthermore, for example, methoxy, ethoxy, propoxy, iospropoxy, butoxy, sec-butoxy, methylthio, ethylthio, propylthio, isopropylthio or butylthio.
  • R 8 radicals are furthermore, for example, fluorine, chlorine or bromine.
  • R 1 radicals are, for example, methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino, isopropylsulfonylamino, butylsulfonylamino, mono- or dimethylaminosulfonylamino, mono- or diethylaminosulfonylamino, mono- or dipropylamino-nylamino, mono- or di-mono-aminylamino, mono- or di-mono-aminylamino, mono- or di-mono-aminylamino, mono- or di-mono-aminylamino, mono- or di-mono-aminylamino, .
  • Residues X 1 , X 3 and R 7 are, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl or butoxycarbonyl.
  • Residues X 1 and R 7 are furthermore, for example, pentyloxycarbonyl, hexyloxycarbonyl, mono- or dimethylcarbamoyl, mono- or diethylcarbamoyl, mono- or dipropylcarbamoyl, mono- or diisopropylcarbamoyl, mono- or dibutylcarbamoyl or N-methyl-N-ethylcarbamoyl.
  • X 1 radicals are furthermore, for example, 2-methoxyethoxycarbonyl, 2-ethoxyethoxycarbonyl, 3,6-dioxaheptyloxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, cycloheptyloxycarbonyl, formyl, acetyl, propionyl, butyryl, isobutyryl,
  • a method is particularly preferred in which there are one or more dyes of the formula I on the support, in which B represents the residue of a CH-acidic compound which is derived from a compound of the formula IIa or IIb.
  • the methine dyes of the formula I can be prepared by methods known per se, as described, for example, in JP-A-32 164/1990, in the earlier application EP-A-416 434 or in the earlier German patent application P 41 05 197.1 (EP-A -0 499 822) are 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 the subtractive color mixture (higher color purity, less blue absorption, more favorable form of the absorption band, eg narrow half-width or greater edge steepness on the short-wave side).
  • they are particularly advantageous for dye mixtures with red or reddish-violet dyes.
  • Such dyes are for example from EP-A-216 483, EP-A-209 990, EP-A-312 211, US-A-4 698 651, EP-A-346 729 or the earlier applications EP-A-416 434, EP-A-441 208 or EP-A-460 463.
  • the dyes of the formula I in combination with violet dyes, produce highly brilliant magenta stains and, in combination with cyan dyes, highly brilliant, reddish blue stains. At the same time, a deep, neutral black is achieved in combination with suitable yellow dyes.
  • 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.
  • Suitable organic solvents for the dyes I are e.g. those in which the solubility of the dyes I at room temperature 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.
  • Preferred binders are ethyl cellulose, ethyl hydroxyethyl cellulose, polyvinyl butyrate, polyvinyl acetate or saturated linear polyesters.
  • the weight ratio of binder: dye is generally 1: 1 to 5: 1.
  • auxiliaries are release agents, such as those mentioned in the earlier application EP-A-441 282 or the corresponding patent applications cited therein. They are also particularly organic To name additives that prevent the transfer dyes from crystallizing out when the ribbon is stored or heated, for example cholesterol or vanillin.
  • Suitable inert carriers are e.g. described in the earlier application EP-A-441 282 or in the corresponding patent applications cited therein.
  • 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. Further details can e.g. from the earlier application EP-A-441 282 or the corresponding patent applications cited therein.
  • 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 table were processed according to ⁇ ) and the resulting, dye-coated supports according to ⁇ ) tested for the transfer behavior.
  • the table shows the thermal transfer parameters T * and ⁇ E T , the absorption maxima of the dyes ⁇ max (measured in methylene chloride) and the binders used.

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

Claims (3)

  1. Procédé de transfert de colorants méthiniques entre un support et un papier enduit de matière plastique, par diffusion 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

            K-N=B     (I)

    dans laquelle
    K   est mis pour un reste de formule
    Figure imgb0013
    Figure imgb0014
     où
    n   est mis pour 0 ou 1
    R1   représente un atome d'hydrogène, un reste méthyle, méthoxy, mono- ou di(alkyl en C1-C4)aminosulfonylamino, (alkyl en C1-C4)sulfonylamino ou le reste -NHCOR9 ou -NHCO2R9, R9 représentant un groupement phényle, benzyle, tolyle ou alkyle en C1-C8 qui est éventuellement interrompu par un ou deux atomes d'oxygène en fonction éther,
    R2   représente un atome d'hydrogène ou un reste méthyle, méthoxy ou éthoxy,
    R3 et R4   sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène, 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 un reste cycloalkyle en C5-C7,
    R5   représente un reste alkyle en C1-C8 qui est éventuellement substitué et peut être interrompu par un ou deux atomes d'oxygène en fonction éther, un reste cycloalkyle en C5-C7, phényle ou tolyle,
    R6   représente un atome d'hydrogène ou d'halogène, un reste alkyle en C1-C6, phényle éventuellement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4, benzyle éventuellement substitué par un grpoupement alkyle en C1-C4 ou alcoxy en C1-C4, cyclohexyle, thiényle, hydroxy ou monoalkylamino en C1-C8,
    R7   représente un reste cyano, carbamoyle, mono- ou di(alkyl en C1-C6)carbamoyle ou (alcoxy en C1-C6)carbonyle, et
    R8   représente un atome d'halogène ou d'hydrogène ou un reste alkyle en C1-C4, alcoxy en C1-C4, alkylthio en C1-C4 ou phényle éventuellement substitué par un groupement alkyle en C1-C4,
    et
    B   est mis pour le reste d'un composé CH-acide qui dérive du nitrométhane, du nitroéthane, du benzimidazol-2-ylacétamide ou d'un composé de formule
    Figure imgb0015
     où
    X1   représente un reste cyano, nitro, alcanoyle en C1-C4, alkylsulfonyle en C1-C4, phénylsulfonyle éventuellement substitué par un groupement alkyle en C1-C4, alcoxy en C1-C4 ou par un atome d'halogène, carboxyle, (alcoxy en C1-C6)carbonyle éventuellement interrompu par 1 ou 2 atomes d'oxygène en fonction éther, (cycloalcoxy en C5-C7)carbonyle, phénoxycarbonyle éventuellement substitué par un groupement alkyle en C1-C4, alcoxy en C1-C4 ou par un atome d'halogène, carbamoyle, mono- ou di(alkyl en C1-C6)carbamoyle éventuellement interrompu par 1 ou 2 atomes d'oxygène en fonction éther, mono- ou di(cycloalkyl en C5-C7)carbamoyle, phénylcarbamoyle éventuellement substitué par un groupement alkyle en C1-C4, alcoxy en C1-C4 ou par un atome d'halogène, benzothiazol-2-yle, 5-phényl-1,3,4-thiadiazol-2-yle ou 2-hydroxyquinoxaline-3-yle,
    X2   représente un reste alkyle en C1-C4 ou alcoxy en C1-C4,
    X3   représente un reste (alcoxy en C1-C4)carbonyle, phénylcarbamoyle ou benzimidazol-2-yle,
    X4   représente un reste alkyle en C1-C4 et
    X5   représente un atome d'hydrogène ou un reste alkyle en C1-C4 ou phényle.
  2. Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants de formule I dans laquelle B est mis pour le reste d'un composé CH-acide qui dérive d'un composé de formule IIa ou IIb.
  3. Procédé selon la revendication 1, caractérisé en ce qu'il se trouve, sur le support, un ou plusieurs colorants de formule I dans laquelle K est mis pour un reste de formule IIIa, IIIc, IIIj, IIIk, IIIl ou IIIm.
EP92105403A 1991-04-18 1992-03-28 Procédé pour le transfert de colorants méthiniques Expired - Lifetime EP0509302B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4112654 1991-04-18
DE4112654A DE4112654A1 (de) 1991-04-18 1991-04-18 Verfahren zur uebertragung von methinfarbstoffen

Publications (2)

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EP0509302A1 EP0509302A1 (fr) 1992-10-21
EP0509302B1 true EP0509302B1 (fr) 1997-01-29

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US (1) US5256624A (fr)
EP (1) EP0509302B1 (fr)
JP (1) JP3272393B2 (fr)
KR (1) KR920019548A (fr)
CA (1) CA2064340A1 (fr)
DE (2) DE4112654A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69613208T2 (de) * 1996-02-27 2002-04-25 Agfa Gevaert Nv Farbstoffdonorelement zum Gebrauch in einem thermischen Übertragungsdruckverfahren
DE19611351A1 (de) 1996-03-22 1997-09-25 Basf Ag Farbstoffmischungen, enthaltend Thienyl- und/oder Thiazolazofarbstoffe
WO2011045253A1 (fr) 2009-10-13 2011-04-21 Basf Se Mélanges pour produire des couches photoactives pour des cellules solaires organiques et des photodétecteurs organiques

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0499822A1 (fr) * 1991-02-20 1992-08-26 BASF Aktiengesellschaft Colorants méthiniques bichromophores

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DE3676245D1 (de) * 1985-07-23 1991-01-31 Ici Plc Thermouebertragungsdruck.
GB8521327D0 (en) * 1985-08-27 1985-10-02 Ici Plc Thermal transfer printing
JPH0749535B2 (ja) * 1985-09-12 1995-05-31 三井東圧化学株式会社 新規な色素体生成法
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US4933315A (en) * 1987-02-20 1990-06-12 Dai Nippon Insatsu Kabushiki Kaisha Heat transfer sheet
GB8724028D0 (en) * 1987-10-13 1987-11-18 Ici Plc Thermal transfer printing
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JPH0232164A (ja) * 1988-07-20 1990-02-01 Sumitomo Chem Co Ltd α−シアノアゾメチン系化合物、その製法及びそれを用いてなる光情報記録媒体
JPH0284390A (ja) * 1988-09-21 1990-03-26 Hitachi Ltd 熱転写シート
JP2844345B2 (ja) * 1989-05-02 1999-01-06 大日本印刷株式会社 熱転写シート
US5223476A (en) * 1989-05-02 1993-06-29 Dai Nippon Insatsu Kabushiki Kaisha Heat transfer sheet
JPH02292371A (ja) * 1989-05-02 1990-12-03 Sankyo Kagaku Kk 感熱転写記録用色素
DE3929698A1 (de) * 1989-09-07 1991-03-14 Basf Ag Triazolopyridinfarbstoffe sowie ein verfahren zum thermischen transfer von methinfarbstoffen
DE4003780A1 (de) * 1990-02-08 1991-08-14 Basf Ag Verwendung von azofarbstoffen fuer den thermotransferdruck
DE4004612A1 (de) * 1990-02-15 1991-08-22 Basf Ag Neue bichromophore methin- und azamethinfarbstoffe und ein verfahren zu ihrer uebertragung
DE69012789T2 (de) * 1990-03-01 1995-02-23 Agfa Gevaert Nv Farbstoffe zur Anwendung in der thermischen Farbstoffübertragung.
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Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0499822A1 (fr) * 1991-02-20 1992-08-26 BASF Aktiengesellschaft Colorants méthiniques bichromophores

Also Published As

Publication number Publication date
EP0509302A1 (fr) 1992-10-21
DE59207973D1 (de) 1997-03-13
CA2064340A1 (fr) 1992-10-19
DE4112654A1 (de) 1992-10-22
KR920019548A (ko) 1992-11-19
US5256624A (en) 1993-10-26
JP3272393B2 (ja) 2002-04-08
JPH05104863A (ja) 1993-04-27

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