EP0344592B1 - Procédé de transfert de colorants azoiques - Google Patents

Procédé de transfert de colorants azoiques Download PDF

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Publication number
EP0344592B1
EP0344592B1 EP89109327A EP89109327A EP0344592B1 EP 0344592 B1 EP0344592 B1 EP 0344592B1 EP 89109327 A EP89109327 A EP 89109327A EP 89109327 A EP89109327 A EP 89109327A EP 0344592 B1 EP0344592 B1 EP 0344592B1
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Prior art keywords
alkyl
alkoxy
phenyl
formula
substituted
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German (de)
English (en)
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EP0344592A2 (fr
EP0344592A3 (en
EP0344592B2 (fr
Inventor
Karl-Heinz Etzbach
Gunther Lamm
Helmut Reichelt
Ruediger 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
    • 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
    • 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 azo dyes, which have a thiophene-based diazo component, from a support onto a plastic-coated paper with the aid of a thermal head.
  • a transfer sheet which contains a thermally transferable dye in one or more binders, optionally together with suitable auxiliaries, on a support is heated with a heating head with short heating pulses (duration: fractions of a second) from the back, whereby the dye migrated from the transfer sheet and diffused into the surface coating of a recording medium.
  • 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.
  • EP-A-216 483 and EP-A-258 856 describe azo dyes which have thiophene-based diazo components and aniline-based coupling components.
  • disazo dyes based on thiophene and aniline are known from EP-A-218 937 for this purpose.
  • EP-A-302 628 which is state of the art for all designated contracting states in accordance with Art. 54 (3) EPC.
  • EP-A-133 011 and EP-A-133 012 deal with the construction of a slave sheet during dye transfer.
  • Residues Y in Formula 1 are e.g. Ethylene, 1,2- or 1,3-propylene, 1,2-, 1,3-, 1,4- or 2,3-butylene, pentamethylene, hexamethylene or 2-methylpentamethylene.
  • Suitable radicals R 1 , R 2 , R 3 , R 4 and R 6 in formula 1 are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl.
  • R 1 , R 2 and R 3 are, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl.
  • R 1 and R 2 are, for example, undecyl, dodecyl, tridecyl, isotridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or eicosyl.
  • the designations isooctyl, isononyl, isodecyl and isotridecyl are trivial designations and come from the alcohols obtained after oxosynthesis (cf. Ullmanns Enzyklopadie der technical chemistry, 4th edition, volume 7, pages 215 to 217 and volume 11, pages 435 and 436 ).
  • R 3 and R 4 are furthermore, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy or sec-butoxy.
  • R 3 radicals are furthermore, for example, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy or decyloxy.
  • R 4 radicals are also, for example, methylthio, ethylthio, propylthio, isopropylthio or butylthio.
  • R 1 and R 2 are furthermore, for example, benzyl, 1- or 2-phenylethyl,
  • the new process uses a carrier on which there are one or more azo dyes of the formula I in which
  • a support is used on which there are one or more azo dyes of the formula I in which R 5 is cyano or the radical -CO-OR ', where R 1 is alkyl, alkanoyloxyalkyl or alkyloxycarbonylalkyl, where these radicals can each have up to 12 carbon atoms, or for the radical of the abovementioned formula III, in which n and R 7 each have the abovementioned meaning, or R 7 in particular represents C 1 -C 6 -alkyl.
  • the dyes of formula 1 are known from EP-A-201 896 or can be obtained by the methods mentioned there.
  • the dyes 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 photochemical stability, easier technical accessibility, better resistance to moisture and chemical substances, higher color strength , better solubility and especially from higher color purity.
  • the dyes are in a suitable organic solvent, for. B. chlorobenzene, isobutanol, methyl ethyl ketone, methylene chloride, toluene, tetrahydrofuran or mixtures thereof with one or more binders, optionally with the addition of auxiliaries, processed to a printing ink.
  • a printing ink contains the dye preferably in a molecularly disperse dissolved form.
  • the printing ink is applied to the inert carrier using a doctor blade and the dyeing is air-dried.
  • 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. 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 are cellulose derivatives, e.g. B. methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyl resin, vinyl resin, polyvinyl alcohol, polyvinyl acetate, polyvinyl butyrate or polyvinyl pyrrolidone.
  • cellulose derivatives e.g. B. methyl cellulose, ethyl cellulose, ethyl hydroxyethyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, starch, alginates, alkyl 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 resins, polyamide resins, polyurethane resins or natural CH resins, such as gum arabic, are also suitable as binders. Further suitable binders are described in DE-A-3 524 519.
  • Preferred binders are ethyl cellulose or ethyl hydroxyethyl cellulose of medium to small viscosity settings.
  • the ratio of binder to dye preferably varies between 5: 1 and 1: 1.
  • auxiliaries such as are specified in EP-A-227 092, EP-A-192 435 or the patent applications cited therein, are also suitable as auxiliaries, in addition, in particular, organic additives which cause the transfer dyes to crystallize out during storage and when the ink ribbon is heated prevent e.g. B. cholesterol or vanillin.
  • Inert carriers are e.g. B. tissue, blotting paper or glassine paper or plastic films with good heat resistance, e.g. B. optionally metal-coated polyester, polyamide or polyimide.
  • the inert carrier is optionally additionally coated with a lubricating layer (slipping layer) in order to prevent the thermal head from sticking to the carrier material.
  • Suitable lubricants are e.g. B. 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.
  • thermostable plastic layers with an affinity for the dyes to be transferred can be used as the dye-receiving layer.
  • Your glass transition temperature should be below 150 ° C.
  • Modified polycarbonates or polyesters may be mentioned as examples.
  • Suitable formulations for the receiver layer composition are e.g. B. 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 transfer takes place by means of a thermal head, which must 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)
  • Printing Methods (AREA)
  • Coloring (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (7)

1. Procédé pour le transfert de colorants azoïques entre un support et un papier enduit de matière plastique par diffusion a l'aide d'une tête thermique, caractérisé en ce qu'on utilise un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I
Figure imgb0060
dans laquelle
R1 et R2 sont identiques ou différents et représentent chacun, indépendamment l'un de l'autre, un reste alkyle, alcanoyloxyalkyle, alcoxycarbonyloxyalkyle ou alcoxycarbonylalkyle, ces restes pouvant comporter chacun jusqu'à 20 atomes de carbone et pouvant être substitués par des groupements phényle, alkyl(en C1-C4)phényle, alcoxy(en C1-C4)-phényle, benzyloxy, alkyl(en C1-C4)benzyloxy, alcoxy(en C1-C4)benzyloxy, halogéno, hydroxy ou cyano, un atome d'hydrogène, un reste phényle éventuellement substitué par un groupement alkyle en C1-C20, alcoxy en C1-C20 ou halogéno, un reste benzyle éventuellement substitué par un groupement alkyle en C1-C20, alcoxy en C1-C20 ou halogéno, ou un reste de formule II
Figure imgb0061
où
Y est mis pour un reste alkylène en C2-C6,
m est mis pour 1, 2, 3, 4, 5 ou 6 et
R6 est mis pour un reste alkyle en C1-C4 ou phényle éventuelement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4,
R3 représente un atome d'hydrogène, un reste alkyle en Ci -Ci o, alcoxy en Ci -Ci 0 ou le reste -NH-CO-R1, R1 ayant la signification donnée ci-dessus,
R4 représente un atome d'hydrogène, de chlore ou un reste alkyle en C1-C4, alcoxy en C1-C4, alkyl(en C1-C4)thio ou phényle éventuellement substitué par un groupement alkyle en C1-C4, alcoxy en C1-C4 ou par un atome d'halogène, et
R6 représente un groupement cyano ou le reste -CO-OR1, -CO-NHR1 ou -CONR1R2, R1 et R2 ayant chacun la signification donnée ci-dessus, les composés suivants étant exclus:
Figure imgb0062
Figure imgb0063
2. Procédé selon la revendication 1, caractérisé en se qu'on utilise un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I, dans laquelle
R1 et R2 représentent chacun, indépendamment l'un de l'autre, un reste alkyle, alcanoyloxyalkyle, ou alkyloxycarbonylalkyle, ces restes pouvant comporter chacun jusqu'à 12 atomes de carbone et pouvant être substitués par des groupements phényle, alkyl(en C1-C4)-phényle, alcoxy(en C1-C4)phényle, hydroxy ou cyano, un reste phényle éventuellement substitué par un groupement alkyle en C1-C1 2 ou alcoxy en C1-12, un reste benzyle éventuellement substitué par un groupement alkyle en C1-C12 ou alcoxy en C1-C12, ou un reste de formule II
Figure imgb0064
où
Y est mis pour un reste alkylène en C2-C4,
m est mis pour 1, 2, 3 ou 4 et
R6 est mis pour un reste alkyle en C1-C4 ou phényle éventuelement substitué par un groupement alkyle en C1-C4 ou alcoxy en C1-C4,
R3 représente un atome d'hydrogène, un reste alkyle en C1-C6, alcoxy en C1-C6 ou le reste -NH-CO-R1, R1 ayant la signification donnée ci-dessus,
R4 représente un atome d'hydrogène, de chlore ou un reste alkyle en C1-C4, alcoxy en C1-C4, ou phényle, et
R5 représente un groupement cyano ou le reste -CO-OR1, -CO-NHR1 ou -CONR1R2, R1 et R2 ayant chacun la signification donnée ci-dessus.
3. Procédé selon la revendication 1, caractérisé en ce qu'on utilise un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I, dans laquelle
R1 et R2 représentent chacun, indépendament l'un de l'autre, un reste alkyle en C1-C12 qui est éventuellement substitué par un groupement cyano, phényle, alkyle(en C1-C4)phényle ou alcoxy(en C1-C4)phényle, ou un reste de formule III
Figure imgb0065
où
n est mis pour 1, 2, 3 ou 4 et
R7 est mis pour un reste alkyle en Ci -C4 ou phényle,
R3 représente un atome d'hydrogène ou un reste méthyle, méthoxy ou acétylamino,
R4 représente un atome de chlore et
R5 représente un groupement cyano ou le reste -CO-OR1, -CO-NHR1 ou -CONR1R2, R1 et R2 ayant chacun la signification donnée ci-dessus.
EP89109327A 1988-05-31 1989-05-24 Procédé de transfert de colorants azoiques Expired - Lifetime EP0344592B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3818404A DE3818404A1 (de) 1988-05-31 1988-05-31 Verfahren zur uebertragung von azofarbstoffen
DE3818404 1988-05-31

Publications (4)

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EP0344592A2 EP0344592A2 (fr) 1989-12-06
EP0344592A3 EP0344592A3 (en) 1990-04-04
EP0344592B1 true EP0344592B1 (fr) 1993-09-01
EP0344592B2 EP0344592B2 (fr) 1997-10-15

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US (1) US5037798A (fr)
EP (1) EP0344592B2 (fr)
JP (1) JP2746656B2 (fr)
DE (2) DE3818404A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4004600A1 (de) * 1990-02-15 1991-08-22 Basf Ag Verfahren zur uebertragung von azofarbstoffen
DE4132074A1 (de) * 1991-09-26 1993-04-01 Basf Ag Azofarbstoffe mit einer kupplungskomponente aus der chinolinreihe
WO1994008797A1 (fr) * 1992-10-21 1994-04-28 Imperial Chemical Industries Plc Impression par transfert thermique et par diffusion de colorant
EP0665117A1 (fr) * 1994-01-31 1995-08-02 Agfa-Gevaert N.V. Image produite par transfert thermique de colorant, ayant une stabilité à la lumière améliorée
US8274649B2 (en) 2008-06-24 2012-09-25 International Business Machines Corporation Failure detection in lighting systems
US7518715B1 (en) * 2008-06-24 2009-04-14 International Business Machines Corporation Method for determination of efficient lighting use
CN109574880B (zh) * 2017-09-29 2022-06-17 纳莹(上海)生物科技有限公司 一种荧光探针及其制备方法和用途

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58215397A (ja) * 1982-06-08 1983-12-14 Sony Corp 気化性色素組成物
JPS59204658A (ja) * 1983-05-09 1984-11-20 Gosei Senriyou Gijutsu Kenkyu Kumiai 水不溶性モノアゾ化合物及びそれを用いる疎水性繊維の染色又は捺染法
JPS60239292A (ja) * 1984-05-11 1985-11-28 Mitsubishi Chem Ind Ltd 感熱転写記録用色素
DE3427200A1 (de) * 1984-07-24 1986-01-30 Basf Ag, 6700 Ludwigshafen Methinfarbstoffe
JPS61127392A (ja) * 1984-11-28 1986-06-14 Matsushita Electric Ind Co Ltd 昇華転写用受像体
JPH0725218B2 (ja) * 1985-04-15 1995-03-22 大日本印刷株式会社 被熱転写シ−ト
IN167384B (fr) * 1985-05-14 1990-10-20 Basf Ag
JPH0714665B2 (ja) * 1985-06-10 1995-02-22 大日本印刷株式会社 被熱転写シ−ト
DE3630279A1 (de) * 1986-09-05 1988-03-17 Basf Ag Verfahren zur uebertragung von farbstoffen
GB8718431D0 (en) * 1987-08-04 1987-09-09 Ici Plc Thermal transfer printing

Also Published As

Publication number Publication date
DE3818404A1 (de) 1989-12-07
JP2746656B2 (ja) 1998-05-06
DE58905420D1 (de) 1993-10-07
EP0344592A2 (fr) 1989-12-06
EP0344592A3 (en) 1990-04-04
US5037798A (en) 1991-08-06
EP0344592B2 (fr) 1997-10-15
JPH0225384A (ja) 1990-01-26

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