EP0441208B1 - Utilisation de colorants azoiques pour l'impression thermique - Google Patents

Utilisation de colorants azoiques pour l'impression thermique Download PDF

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Publication number
EP0441208B1
EP0441208B1 EP91101022A EP91101022A EP0441208B1 EP 0441208 B1 EP0441208 B1 EP 0441208B1 EP 91101022 A EP91101022 A EP 91101022A EP 91101022 A EP91101022 A EP 91101022A EP 0441208 B1 EP0441208 B1 EP 0441208B1
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Prior art keywords
alkyl
alkoxy
phenyl
formula
substituted
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German (de)
English (en)
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EP0441208A1 (fr
Inventor
Volker Bach
Karl-Heinz Etzbach
Sabine Gruettner
Helmut Reichelt
Ruediger Sens
Gunther Lamm
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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 main heat source used is a thermal head with which short heating pulses lasting a fraction of a second can be emitted.
  • a transfer sheet which contains the dye to be transferred together with one or more binders, a carrier material and possibly other auxiliaries such as release agents or crystallization-inhibiting substances is heated from the rear by the thermal head.
  • the dye diffuses from the transfer sheet into the surface coating of the substrate, e.g. into the plastic layer of a coated paper.
  • the main advantage of this method is that the amount of ink transferred and thus the color gradation can be controlled in a targeted manner via the energy to be delivered to the thermal head.
  • Thermal transfer printing generally uses the three subtractive primary colors yellow, magenta and cyan, possibly also black, whereby the dyes used must have the following properties for optimal color recording: easy thermal transferability, low tendency to migrate within or from the surface coating of the recording medium at room temperature , high thermal and photochemical stability as well as resistance to moisture and chemicals, no tendency to crystallize when storing the transfer sheet, a suitable color for the subtractive color mixture, a high molar absorption coefficient and easy technical accessibility.
  • magenta dyes previously used cannot convince. This also applies, for example, to the azo dyes described in US Pat. No. 4,764,178 and recommended for thermal transfer, which are similar to azo dyes I and have coupling components based on aniline, tetrahydroquinoline, aminoquinoline or julolidine.
  • azo dyes I themselves are known per se or according to known methods, for example according to the older German patent application P 38 33 443.7, according to 0. Annen et al., Rev. Prog. Coloration 17, 72-85 (1987) or MA Weaver and L. Shuttleworth, Dyes and Pigments 3, 81-121 (1982).
  • the invention was therefore based on the object of finding suitable red and blue dyes for thermal transfer printing which come closer to the required property profile than the dyes known hitherto.
  • a method for transferring azo dyes by diffusion from a support onto a plastic-coated substrate using a thermal head was found, which is characterized in that a support is used for this purpose, on which one or more of the azo dyes I defined at the outset are located.
  • Suitable alkyl radicals Rl , R 2, R 3, R 4, R5, R6, R7, R 8 , R 11 , R12, R 13 , R 15 or R 16 are especially methyl, ethyl, propyl, isopropyl and butyl, in addition also isobutyl, sec-butyl and tert-butyl.
  • the radicals R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 15 or R 16 are, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, To name octyl, 2-ethylhexyl and the isomer mixture isooctyl and cyclohexyl.
  • R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 15 or R 16 are, for example, nonyl and decyl and their isomer mixtures isononyl and isodecyl.
  • undecyl, dodecyl, tridecyl and its isomer mixture isotridecyl, tetradecyl, pentadecyl are also suitable as radicals R 1 , R 2 or R 3 , and also hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl as radicals R 2 and R 3 .
  • alkoxyalkyl groups those which contain up to 8 carbon atoms are also suitable as radicals R 8 and those with up to 12 carbon atoms are also suitable as radicals R 15 or R 16 .
  • Preferred alkoxy groups as R 2 , R 3 , R 8 , R 11 or R 12 are, for example: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and sec-butoxy.
  • R 8 in particular R 2 or R 3, are furthermore, for example, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy, octyloxy and 2-ethylhexyloxy.
  • radicals R 2 or R 3 are, for example, nonyloxy or decyloxy, and also undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy and pentadecyloxy.
  • R 8 radicals can also be alkylthio groups, such as preferably methylthio, ethylthio and 2-cyanoethylthio, in addition propylthio, isopropylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, 2-ethylhexylthio, 2-ethoxycarbonylethylthio and especially 2-methoxycarbonyl.
  • alkylthio groups such as preferably methylthio, ethylthio and 2-cyanoethylthio, in addition propylthio, isopropylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, 2-ethylhexylthio, 2-ethoxycarbonylethylthio and especially 2-methoxycarbonyl.
  • radicals R 1 are C 1 -C 8 -alkyl, including in particular methyl and isopropyl, cyclohexyl, phenyl, which can also carry methoxy, sulfonamido or chlorine as substituents, and also benzyl.
  • Preferred radicals R 1 are furthermore thien-3-yl and especially thien-2-yl, furan-3-yl and especially furan-2-yl as well as pyrid-2-yl, pyrid-4-yl and especially pyrid-3- yl.
  • Preferred radicals R 2 or R 3 of the alkyl radicals mentioned are those with up to 12 C atoms, including in particular methyl, ethyl and propyl, of the cyanoalkyl and alkoxy radicals mentioned those with up to 10 C atoms.
  • Particularly preferred radicals R 2 or R 3 have the formula Ila with methyl or ethyl as the radical R4 '.
  • the dyes to be used according to the invention are distinguished from the red and blue dyes with coupling components based on aniline, which have been used for thermal transfer printing to date, by the following properties: easier thermal transferability, improved migration properties in the recording medium at room temperature, higher thermal stability, higher lightfastness, better resistance to moisture and Chemicals, better solubility in the production of the printing ink, higher color strength and easier technical accessibility.
  • the azo dyes show a significantly better color purity, especially in dye mixtures, and result in improved black prints.
  • the transfer sheets required as dye donors for the thermal transfer printing process according to the invention are prepared as follows:
  • the azo dyes are in an organic solvent such as isobutanol, methyl ethyl ketone, methylene chloride, chlorobenzene, toluene, tetrahydrofuran or mixtures thereof, with one or more binders and possibly other auxiliaries such as release agents or crystallization-inhibiting substances processed into a printing ink, which preferably contains the dyes in a molecularly dispersed solution.
  • the printing ink is then applied to an inert support and dried.
  • Suitable binders for the use of the azo dyes according to the invention are all materials which are soluble in organic solvents and which are known to be used for thermal transfer printing, e.g. Cellulose derivatives such as methyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, especially ethyl cellulose and ethyl hydroxyethyl cellulose, starch, alginates, alkyd resins such as polyvinyl alcohol or polyvinyl pyrrolidone, and especially polyvinyl acetate and polyvinyl butyrate.
  • Cellulose derivatives such as methyl cellulose, hydroxypropyl cellulose, cellulose acetate or cellulose acetobutyrate, especially ethyl cellulose and ethyl hydroxyethyl cellulose, starch, alginates, alkyd resins such as polyvinyl alcohol or polyvinyl pyrrolidone, and especially polyvinyl acetate and
  • 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 resins such as e.g. Gum arabic into consideration.
  • binders are often recommended, e.g. those made of ethyl cellulose and polyvinyl butyrate in a weight ratio of 2: 1.
  • the weight ratio of binder to dye is usually 8: 1 to 1: 1, preferably 5: 1 to 2: 1.
  • Inert carrier materials are, for example, tissue paper, blotting paper or glassine paper as well as films made of heat-resistant plastics such as polyesters, polyamides or polyimides, these films also being able to be metal-coated.
  • the inert carrier can additionally be coated with a lubricant on the side facing the thermal head in order to prevent the thermal head from sticking to the carrier material.
  • Suitable lubricants are, for example, silicones or polyurethanes, as described in EP-A-216 483.
  • the thickness of the dye carrier is generally 3 to 30 microns, preferably 5 to 10 microns.
  • the substrate to be printed e.g. Paper, for its part, must be coated with a plastic that absorbs the dye during the printing process.
  • a plastic that absorbs the dye during the printing process.
  • Polymeric materials whose glass transition temperature Tg is between 50 and 100 ° C, i.e. e.g. Polycarbonate and polyester. Further details can be found in EP-A-227 094, EP-A-133 012, EP-A-133 011, JP-A-199 997/1986 or JP-A-283 595/1986.
  • a thermal head which can be heated to temperatures up to over 300 ° C., so that the dye transfer takes place within a maximum time of 15 msec.
  • transfer sheets were produced in the usual way from polyester film of 6 to 10 ⁇ m thick, which was provided with an approximately 5 ⁇ m thick transfer layer made of a binder B, which each contained approximately 0.25 g of azo dye I.
  • the weight ratio of binder to dye was 4: 1, unless otherwise stated in the tables below.
  • the substrate to be printed consisted of paper approximately 120 ⁇ m thick, which was coated with an 8 ⁇ m thick plastic layer (Hitachi Color Video Print Paper).
  • the coated side of the encoder and slave was placed on top of one another and wrapped in aluminum foil and heated for two minutes between two hot plates to a temperature between 70 and 80 ° C. With similar samples, this process was repeated three times at a higher temperature between 80 and 120 ° C.
  • the amount of dye diffused into the plastic layer of the receiver is proportional to the optical density, which was determined as absorbance A photometrically after the respective heating to the temperatures given above.
  • the temperature T * at which the extinction reaches the value 1 can also be taken from the application, ie the transmitted light intensity is one tenth of the incident light intensity.
  • the smaller the temperature T * the better the thermal transferability of the investigated dye.
  • binder B used in each case.
  • EC ethyl cellulose
  • PVB polyvinyl butyrate
  • VY Vylon.

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

Claims (3)

1. Utilisation de colorants azoïques de formule générale 1
Figure imgb0057
pour l'impression par transfert thermique, dans laquelle les substituants ont la signification suivante :
R1 un atome d'hydrogène;
des groupes alkyle en C1-C15, qui peuvent comporter des groupes phényle ou phénoxy en tant que substituants;
un groupe cyclohexyle, qui peut comporter des groupes alkyle en C1-C5, alcoxy en C1-C5 ou halogéno en tant que substituants;
un groupe phényle, qui peut comporter des groupes alkyle en C1-C5, alcoxy en C1-C5, sulfonamido ou halogéno en tant que substituants;
un groupe thiényle, qui peut comporter des groupes alkyle en C1-C5 ou halogéno en tant que substituants,
un groupe furanyle ou pyridyle;
un reste de formule générale Il
Figure imgb0058
dans laquelle
W désigne des groupes alkylène en C2-C6 identiques ou différents,
n représente un nombre de 1 à 6 et
R4 est mis pour un groupe alkyle en C1-C4 ou un groupe phényle ou benzyle, les deux groupes pouvant comporter chacun des groupes alkyle en C1-C4 ou alcoxy en C1-C4 en tant que substituants;
R2, R3 un atome d'hydrogène;
des groupes alkyle, alcoxy, alcoxyalkyle, alcanoyloxyalkyle, alcoxycarbonyloxyalkyle, al- coxycarbonylalkyle, halogénoalkyle, hydroxyalkyle ou cyanoalkyle, qui peuvent contenir chacun jusqu'à 15 atomes de carbone et comporter des groupes phényle, (alkyle en C1-C4)phényle, (alcoxy en C1-C4)phényle, halogénophényle, benzyloxy, (alkyle en C1-C4)benzyloxy, (alcoxy en C1-C4)benzyloxy, halogénobenzyloxy, halogéno, hydroxy ou cyano, en tant que substituants;
un groupe cyclohexyle qui peut comporter des groupes alkyle en C1-C15, alcoxy en C1-C15 ou halogéno en tant que substituants;
un groupe phényle qui peut comporter des groupes alkyle en C1-C15, alcoxy en C1-C15, benzyloxy ou halogéno en tant que substituants;
un reste de foemule Il définie ci-dessus;
D le reste d'un constituant diazoïque III
Figure imgb0059
à l'exclusion des colorants azoïques de formule
Figure imgb0060
dans laquelle les substituants ont la signification suivante :
a) R' = -H, R" = -CH2-C6H5;
b) R' = -CH3, R" = -CeH4-4-CH3;
c) R' = -C2H5, R" = -C6H4-3-CH3;
d) R' = -CH3, R" = -C6H5,

ainsi que de ceux de formule
Figure imgb0061
dans laquelle R" signifie un atome d'hydrogène, un groupe méthyle ou phényle.
2. Procédé de transfert de colorants azoïques par diffusion entre un support et un substrat muni d'un revêtement de matière synthétique au moyen d'une tête thermique, caractérisé en ce que l'on utilise à cette fin un support sur lequel se trouvent un ou plusieurs colorants azoïques de formule I selon la revendication 1.
3. Procédé selon la revendication 2, caractérisé en ce que l'on utilise à cette fin un colorant azoïque de formule la
Figure imgb0062
dans laquelle les substituants ont la signification suivante :
R1' des groupes alkyle en C1-C8, qui peuvent comporter des groupes phényle ou phénoxy en tant que substituants;
un groupe cyclohexyle;
un groupe phényle qui peut comporter des groupes alkyle en C1-C4, alcoxy en C1-C4 ou chloro en tant que substituants;
un groupe thiényle;
un reste de formule générale Ila
Figure imgb0063
 dans laquelle p est mis pour 0 ou 1 et q pour un nombre compris entre 1 et 4, et R4' désigne un groupe alkyle en C1-C4, phényle ou benzyle;
R2', R3' des groupes alkyle en C1-C12, alcoxy en C1-C10 ou cyanoalkyle en C1-C10; un reste de formule Ila décrite ci-dessus;
D' le reste d'un constituant diazoïque III, qui provient de la série des
aniline, phénylazoaniline,
aminothiophène, phénylazoaminothiophène,
aminothiazole, phénylazoaminothiazole,
aminoisothiazole, aminobenzisothiazole,
aminothiadiazole, aminoisothiadiazole,
aminooxazole, aminooxadiazole,
aminodiazole, aminotriazole ou
aminopyrrole
EP91101022A 1990-02-08 1991-01-26 Utilisation de colorants azoiques pour l'impression thermique Expired - Lifetime EP0441208B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4003780A DE4003780A1 (de) 1990-02-08 1990-02-08 Verwendung von azofarbstoffen fuer den thermotransferdruck
DE4003780 1990-02-08

Publications (2)

Publication Number Publication Date
EP0441208A1 EP0441208A1 (fr) 1991-08-14
EP0441208B1 true EP0441208B1 (fr) 1994-05-04

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EP91101022A Expired - Lifetime EP0441208B1 (fr) 1990-02-08 1991-01-26 Utilisation de colorants azoiques pour l'impression thermique

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US (2) US5158928A (fr)
EP (1) EP0441208B1 (fr)
JP (1) JP3001991B2 (fr)
DE (2) DE4003780A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4112654A1 (de) * 1991-04-18 1992-10-22 Basf Ag Verfahren zur uebertragung von methinfarbstoffen
DE4426023A1 (de) * 1994-07-22 1996-01-25 Basf Ag Azofarbstoffe mit einer Kupplungskomponente aus der Aminothiazolreihe
DE19611351A1 (de) * 1996-03-22 1997-09-25 Basf Ag Farbstoffmischungen, enthaltend Thienyl- und/oder Thiazolazofarbstoffe
WO2002080152A2 (fr) * 2001-03-28 2002-10-10 Bayer Aktiengesellschaft Support de donnees optique dont la couche d'informations contient un colorant azoique heterocyclique en tant que compose d'absorption lumineuse
US20080081766A1 (en) * 2006-09-29 2008-04-03 Fujifilm Corporation Image-forming method using heat-sensitive transfer system
EP1974948A3 (fr) 2007-03-29 2012-02-08 FUJIFILM Corporation Procédé de formation d'images utilisant un système de transfert thermosensible
JP2008265319A (ja) * 2007-03-29 2008-11-06 Fujifilm Corp 感熱転写インクシートおよび画像形成方法
US8258300B2 (en) * 2008-09-29 2012-09-04 King Abdulaziz University Azo dyes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0432705A1 (fr) * 1989-12-11 1991-06-19 Eastman Kodak Company Elément d'impression thermique contenant un colorant magenta de 3-aryl-2-arylazo-5-aminothiazole ou -aminothiophène stabilisé par un colorant cyane d'indoaniline

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60239291A (ja) * 1984-05-11 1985-11-28 Mitsubishi Chem Ind Ltd 感熱記録用色素及び感熱記録用シート
GB8504518D0 (en) * 1985-02-21 1985-03-27 Ici Plc Thermal transfer dyesheet
DE3638756A1 (de) * 1986-11-13 1988-05-26 Basf Ag Verfahren zur uebertragung von farbstoffen
DE3928243A1 (de) * 1989-08-26 1991-02-28 Basf Ag Merocyaninartige thiazolfarbstoffe sowie ein verfahren zum thermischen transfer dieser farbstoffe

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0432705A1 (fr) * 1989-12-11 1991-06-19 Eastman Kodak Company Elément d'impression thermique contenant un colorant magenta de 3-aryl-2-arylazo-5-aminothiazole ou -aminothiophène stabilisé par un colorant cyane d'indoaniline

Also Published As

Publication number Publication date
DE59101521D1 (de) 1994-06-09
JP3001991B2 (ja) 2000-01-24
JPH04357088A (ja) 1992-12-10
DE4003780A1 (de) 1991-08-14
USRE34877E (en) 1995-03-14
US5158928A (en) 1992-10-27
EP0441208A1 (fr) 1991-08-14

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