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EP0258856B2 - Méthode de transfert de colorant - Google Patents
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EP0258856B2 - Méthode de transfert de colorant - Google Patents

Méthode de transfert de colorant Download PDF

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Publication number
EP0258856B2
EP0258856B2 EP87112630A EP87112630A EP0258856B2 EP 0258856 B2 EP0258856 B2 EP 0258856B2 EP 87112630 A EP87112630 A EP 87112630A EP 87112630 A EP87112630 A EP 87112630A EP 0258856 B2 EP0258856 B2 EP 0258856B2
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
hydrogen
butyl
benzyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP87112630A
Other languages
German (de)
English (en)
Other versions
EP0258856A3 (en
EP0258856A2 (fr
EP0258856B1 (fr
Inventor
Bernhard Dr. Albert
Karl-Heinz Dr. Etzbach
Ruediger Dr. Sens
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Application filed by BASF SE filed Critical BASF SE
Publication of EP0258856A2 publication Critical patent/EP0258856A2/fr
Publication of EP0258856A3 publication Critical patent/EP0258856A3/de
Application granted granted Critical
Publication of EP0258856B1 publication Critical patent/EP0258856B1/fr
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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
    • 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
    • B41M5/3854—Dyes containing one or more acyclic carbon-to-carbon double bonds, e.g., di- or tri-cyanovinyl, methine
    • 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
    • B41M5/388—Azo dyes
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • a transfer sheet which contains a sublimable dye, optionally together with a binder on a support is heated with a heating head with short (duration: fractions of a second) heating pulses from the back, the dye subliming or evaporating and on a recording medium is transferred.
  • the main advantage of this method is that it is easy to control the amount of dye to be transferred (and thus the color gradation) by adjusting the energy to be delivered to the heating head.
  • the color recording is carried out using the three subtractive primary colors yellow, magenta and cyan (and possibly black).
  • the dyes In order to enable optimal color recording, the dyes must have the following properties:
  • JP-A 159091/1985 describes dyes of the formula in which R is alkyl, aralkyl, aryl or a 5- / 6-membered carbocyclic ring means described for this purpose.
  • JP-A 239292/1985 uses dyes of the formula for the transfer described.
  • R 1 is 1-8 C, alkyl
  • R 2 is H or methyl
  • D is Quinone derivatives of the formula in which R and R 1 denotes methyl, ethyl, propyl or butyl are described for this application in JP-A 229 786/1985.
  • the invention had for its object to provide dyes which are easily sublimable or evaporable under the conditions of a thermal head, which do not undergo thermal and photochemical decomposition, which can be processed into printing inks and which meet the color requirements.
  • the dyes should be technically easily accessible.
  • the dyes used in the process according to the invention are distinguished by better sublimability, in some cases higher light fastness or by higher resistance to chemical substances.
  • R 1 and R 2 include, for example: C 1 -C 4 -alkyl such as CH 3 , C 2 H 5 , n-propyl, isopropyl, n-butyl, isobutyl, tertiary-butyl; C i - to C 4 alkoxy such as methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, tertiary butyloxy; C i to C 4 alkylthio such as methylthio, ethyl and butylthio and halogen such as bromine, preferably chlorine and fluorine.
  • R 1 can also form a heterocyclic ring together with R, so that can correspond to the following formulas: and
  • C i - to C 4 -alkyl which may be mentioned in detail, for example: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl.
  • C 1 -C 4 -alkoxy in the alkoxy-bearing substituents are: methoxy, ethoxy, n- and i-propoxy and n- and i-butoxy.
  • the dyes (I) are synthesized by known or per se known methods.
  • Azo dyes (I) with were synthesized by the method described in DE-A 31 08 077 and 35 29 831.
  • Dyes of the type were developed according to the method described by Mc Kusick et al., J. Am. Chem. Soc. (1958), 80, 2806 described process by reacting the corresponding aniline derivatives with tetracyanoethylene.
  • the dyes are in a suitable solvent, e.g. Chlorobenzene or isobutanol processed with a binder to form a printing ink.
  • a suitable solvent e.g. Chlorobenzene or isobutanol processed with a binder to form a printing ink.
  • the printing ink is applied to the inert carrier using a doctor blade and the dyeing is air-dried.
  • binders e.g. Ethyl cellulose, polysulfones or polyethersulfones into consideration.
  • Inert carriers are e.g. Tissue paper, blotting paper or glassine paper as well as plastic films with good heat resistance, e.g. optionally metal-coated polyester, polyamide or polyimide.
  • the thickness of the support is preferably 3 to 30 ⁇ m. Further suitable carrier materials, binders and solvents for the production of the printing inks are described in DE-A
  • the transfer takes place by means of a thermal head, which must deliver sufficient heating power so that the dye is transferred within a few milliseconds.
  • the paper layer (donor) coated with the dye to be tested is placed with the dye layer on an 80 ⁇ m thick polyester film (receiver) and pressed on.
  • the encoder / receiver is then wrapped with aluminum foil and heated between two heated plates for 30 seconds.
  • the amount of dye migrated into the PES film is determined photometrically. If the logarithm of the absorbance A of the colored polyester films measured at different temperatures (range: 100 to 200 ° C) is plotted against the associated reciprocal absolute temperature, straight lines are obtained, from the slope of which the activation energy AE T for the transfer experiment is calculated:
  • the temperature T * [° C.] is additionally taken from the plots at which the extinction A of the colored polyester film reaches the value 1.
  • the dyes given in Tables 1 to 6 were processed according to Al) or All) and the dye-coated supports obtained according to B) were tested for the sublimation behavior.
  • the table shows the color shade on polyester as well as the thermal transfer parameters T * and AE T.

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

Claims (9)

1. Procédé de transfert de colorants à partir d'un support, par sublimation/vaporisation au moyen d'une tête thermique, sur un papier revêtu de matière plastique, caractérisé en ce qu'on utilise un support sur lequel se trouvent des colorants de formule générale
Figure imgb0077
dans laquelle
A est mis pour D-N = N- ou
Figure imgb0078
R1 et R2 sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène, un radical alkyle en C1-C4, alcoxy en C1-C2, alkylthio en C1-C4 ou un atome d'halogène, R1 pouvant former, avec R, un noyau hétérocyclique à 5 ou 6 termes, et
R et R' sont mis, indépendamment l'un de l'autre, pour un atome d'hydrogène, un radical alkyle en C1-C4, (alcoxy en C1-C4)-(alkyle en C2), fluoroalkyle en C1-C4, cycloalkyle en C5-C6 ou benzyle, ou
Figure imgb0079
est mis pour un noyau hétérocyclique à 5 ou 6 termes,
D représentant un groupement
Figure imgb0080
R3 représentant CN,
R4 représentant un radical alkyle en C1-C4, phényle, benzyle ou CN,
R5 représentant un radical alkyle en C1-C4, alkylthio en C1-C4, alcoxy en C1-C4, cycloalkyle en C5 ou C6, benzyle, cycloalkylthio en C5 ou C6, cycloalcoxy en C5 ou C6, benzyloxy ou benzylthio,
R6 représentant CN ou -CHO,
R7 représentant un radical alcoxy en C1-C4, alkylthio en C1-C4 ou un atome de chlore et
R8 représentant -CHO ou CN,
R1 et R2 ne pouvant pas être simultanément des atomes d'hydrogène lorsque
A est un groupement
Figure imgb0081
et R5 un reste alkylthio, lorsque
A est un groupement
Figure imgb0082
ou lorsque
A est un groupement
Figure imgb0083
R et R' sont chacun un atome d'hydrogène, un radical alkyle en C1-C4 ou (alcoxy en C1 -C4)-(alkyle en C2).
2. Procédé selon la revendication 1, caractérisé en ce que
R et R' sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en C1-C4, (alcoxy en C1-C4)-(alkyle en C2) ou fluoroalkyle en C1-C4,
R1 et R2 sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en C1-C4 ou alcoxy en C1-C4, et
A est mis pour D-N = N- ou pour
Figure imgb0084
3. Procédé selon la revendication 1 ou 2, caractérisé en ce que
A est mis pour D-N = N-, où D représente
Figure imgb0085
R4 représentant un radical alkyle en C1-C4, phényle, benzyle ou CN et
R5 représentant un radical alkyle en C1-C4, alkylthio en C1-C4, benzyle, cycloalkyle en C5 ou C6, benzylthio ou cycloalkylthio en C5 ou C6.
4. Procédé selon la revendication 1, caractérisé en ce que l'on utilise des colorants de formules générales
Figure imgb0086
ou
Figure imgb0087
dans lesquelles
D est mis pour
Figure imgb0088
R est mis pour un atome d'hydrogène ou pour un radical alkyle en C1-C4, (alcoxy en C1-C4)-(alkyle en C2), fluoroalkyle en C1-C4, cycloalkyle en C5 au C6 ou benzyle,
R4 est mis pour un radical alkyle en C1-C4, phényle, benzyle ou CN et
R5 est mis pour un radical alkyle en C1-C4, alkylthio en C1-C4, benzyle, cycloalkyle en C5 ou C6, benzylthio ou cycloalkylthio en C5 ou C6.
5. Procédé selon la revendication 2, caractérisé en ce que l'on utilise des colorants de formule générale
Figure imgb0089
dans lesquelles
R9 représente un atome d'hydrogène ou un radical alcoxy en C1 -C4 et
R10 et R11 représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un radical alkyle en C1 -C4.
6. Procédé selon la revendication 4, caractérisé en ce que l'on utilise des colorants dans lesquels
D est mis pour
Figure imgb0090
7. Procédé selon la revendication 2, caractérisé en ce que l'on utilise des colorants de formule générale
Figure imgb0091
dans laquelle R, R', R1, R2 et R4 ont les significations indiquées dans la revendication 1.
8. Procédé selon la revendication 7, caractérisé en ce que
R et R' sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en C1-C4, (alcoxy en C1-C4)-(alkyle en C2) ou fluoroalkyle en C1-C4,
R1 et R2 sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en C1-C4, alcoxy en C1-C4 ou alkylthio en C1-C4, et
R4 est mis pour un radical alkyle en C1-C4, phényle, benzyle ou cyano.
9. Procédé selon la revendication 7, caractérisé en ce que
R et R' sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en Ci -C4 ou benzyle,
R1 et R2 sont mis chacun, indépendamment l'un de l'autre, pour un atome d'hydrogène ou pour un radical alkyle en C1-C4, alcoxy en C1-C4 ou thioalkyle en C1-C4, et
R4 est mis pour un radical alkyle en Ci -C4 ou phényle.
EP87112630A 1986-09-05 1987-08-29 Méthode de transfert de colorant Expired - Lifetime EP0258856B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19863630279 DE3630279A1 (de) 1986-09-05 1986-09-05 Verfahren zur uebertragung von farbstoffen
DE3630279 1986-09-05

Publications (4)

Publication Number Publication Date
EP0258856A2 EP0258856A2 (fr) 1988-03-09
EP0258856A3 EP0258856A3 (en) 1988-08-24
EP0258856B1 EP0258856B1 (fr) 1990-11-14
EP0258856B2 true EP0258856B2 (fr) 1994-12-07

Family

ID=6308996

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87112630A Expired - Lifetime EP0258856B2 (fr) 1986-09-05 1987-08-29 Méthode de transfert de colorant

Country Status (4)

Country Link
US (1) US4999026A (fr)
EP (1) EP0258856B2 (fr)
JP (1) JP2677564B2 (fr)
DE (2) DE3630279A1 (fr)

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EP0441396A1 (fr) * 1990-02-09 1991-08-14 Mitsubishi Kasei Corporation Feuille pour l'enregistrement par transfert thermique et encre pour sa fabrication
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EP0593817A1 (fr) * 1992-10-20 1994-04-27 Agfa-Gevaert N.V. Elément donneur de colorant comprenant des colorants de type tricyanovinylaniline
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Also Published As

Publication number Publication date
EP0258856A3 (en) 1988-08-24
JP2677564B2 (ja) 1997-11-17
DE3630279A1 (de) 1988-03-17
EP0258856A2 (fr) 1988-03-09
EP0258856B1 (fr) 1990-11-14
JPS6369693A (ja) 1988-03-29
DE3766194D1 (de) 1990-12-20
US4999026A (en) 1991-03-12

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