EP0257577B1 - N-Alkyl- oder N-Arylaminopyrazolon-merocyanin-Farbstoff-Donor-Element für die thermische Farbstoffübertragung - Google Patents

N-Alkyl- oder N-Arylaminopyrazolon-merocyanin-Farbstoff-Donor-Element für die thermische Farbstoffübertragung Download PDF

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Publication number
EP0257577B1
EP0257577B1 EP19870112145 EP87112145A EP0257577B1 EP 0257577 B1 EP0257577 B1 EP 0257577B1 EP 19870112145 EP19870112145 EP 19870112145 EP 87112145 A EP87112145 A EP 87112145A EP 0257577 B1 EP0257577 B1 EP 0257577B1
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Prior art keywords
dye
substituted
carbon atoms
unsubstituted
merocyanine
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EP19870112145
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English (en)
French (fr)
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EP0257577A3 (en
EP0257577A2 (de
Inventor
Gary Wayne Byers
Steven Evans
Helmut Weber
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Eastman Kodak Co
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Eastman Kodak Co
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Priority claimed from US06/899,273 external-priority patent/US4705521A/en
Priority claimed from US07/059,443 external-priority patent/US4743582A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
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Publication of EP0257577A3 publication Critical patent/EP0257577A3/en
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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
    • B41M5/3854—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
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5227—Macromolecular coatings characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants

Definitions

  • This invention relates to N-alkyl- or N-aryl-aminopyrazolone merocyanine dye-donor elements used in thermal dye transfer which have good stability to light.
  • thermal transfer systems have been developed to obtain prints from pictures which have been generated electronically from a color video camera.
  • an electronic picture is first subjected to color separation by color filters.
  • the respective color-separated images are then converted into electrical signals.
  • These signals are then operated on to produce cyan, magenta and yellow electrical signals.
  • These signals are then transmitted to a thermal printer.
  • a cyan, magenta or yellow dye-donor element is placed face-to-face with a dye-receiving element.
  • the two are then inserted between a thermal printing head and a platen roller.
  • a line-type thermal printing head is used to apply heat from the back of the dye-donor sheet.
  • the thermal printing head has many heating elements and is heated up sequentially in response to the cyan, magenta and yellow signals. The process is then repeated for the other two colors. A color hard copy is thus obtained which corresponds to the original picture viewed on a screen. Further details of this process and an apparatus for carrying it out are contained in U.S. Patent No. 4,621,271 by Brownstein entitled “Apparatus and Method For Controlling A Thermal Printer Apparatus,” issued November 4, 1986.
  • One of the major problems in selecting a dye for thermal dye-transfer printing is to obtain good transfer efficiency to produce high maximum density. Another problem is to obtain such dyes which have good stability to light. Many of the dyes proposed for use are not suitable because they either yield inadequate transfer densities at reasonable coating coverages or have poor light stability.
  • Japanese Patent Publication 60/214994 relates to cyanine or merocyanine dyes which are used in an image recording material. Those dyes, however, are not used in a thermal dye transfer system. Instead, those dyes are light bleachable, such as by flash exposure, to bleach or destroy the dye. Thus, those dyes undergo substantial photolysis or decomposition, when exposed to radiant energy. In addition, those dyes absorb at wavelengths substantially beyond the visible spectrum, unlike the dyes of the present invention.
  • a dye-donor element comprising a support having thereon a dye layer characterized in that the dye comprises a 3-(N-alkyl- or N-aryl-amino)-2-pyrazolin-5-one merocyanine dye dispersed in a polymeric binder, the merocyanine dye being capable of transfer by diffusion to a dye-receiving element upon the application of heat and being incapable of substantial photolysis, the merocyanine dye being substituted or unsubstituted on the bridging methine carbon atoms.
  • the dyes of the invention are "incapable of substantial photolysis” is meant that the dyes of the invention do not undergo any substantial decomposition when exposed to radiant energy.
  • the merocyanine dyes employed in the invention may be of magenta or yellow hue.
  • the merocyanine dye has the formula: wherein: R represents a substituted or unsubstituted alkyl group of from 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl or such alkyl groups substituted with hydroxy, acyloxy, alkoxy, aryl, cyano, acylamido, halogen, etc.; or a substituted or unsubstituted aryl group of from 6 to 10 carbon atoms such as phenyl, p-tolyl, m-chlorophenyl, p-methoxyphenyl, m-bromophenyl, o-tolyl, etc.; R1 and R2 each independently represent hydrogen, with the proviso that only one of R1 and R2 may be hydrogen at the same time; a substituted or unsubstituted alkyl group of from 1
  • Z represents the atoms necessary to complete an indoline ring.
  • R1 and R2 are both methyl.
  • R3 is phenyl.
  • These dyes may be prepared by synthetic procedures similar to those described in copending Application Serial No. , by Byers and Chapman entitled “Merocyanine Dye-Donor Element Used in Thermal Dye Transfer”, filed of even date herewith.
  • a dye-barrier layer comprising a hydrophilic polymer may be employed in the dye-donor element of the invention between its support and the dye layer to improve the density of the transferred dye.
  • the dye in the dye-donor element of the invention is dispersed in a polymeric binder such as a cellulose derivative, e.g., cellulose acetate hydrogen phthalate, cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, cellulose triacetate; a polycarbonate; poly(styrene-co-acrylonitrile), a poly(sulfone) or a poly(phenylene oxide).
  • the binder may be used at a coverage of from 0.1 to 5 g/m2.
  • the dye layer of the dye-donor element may be coated on the support or printed thereon by a printing technique such as a gravure process.
  • any material can be used as the support for the dye-donor element of the invention provided it is dimensionally stable and can withstand the heat of the thermal printing heads.
  • Such materials include polyesters such as poly(ethylene terephthalate); polyamides; polycarbonates; glassine paper; condenser paper; cellulose esters; fluorine polymers; polyethers; polyacetals; polyolefins; and polyimides.
  • the support generally has a thickness of from 2 to 30 ⁇ m. It may also be coated with a subbing layer, if desired.
  • the reverse side of the dye-donor element may be coated with a slipping layer to prevent the printing head from sticking to the dye-donor element.
  • a slipping layer would comprise a lubricating material such as a surface active agent, a liquid lubricant, a solid lubricant or mixtures thereof, with or without a polymeric binder.
  • the dye-receiving element that is used with the dye-donor element of the invention usually comprises a support having thereon a dye image-receiving layer.
  • the support may be a transparent film such as a poly(ether sulfone), a polyimide, a cellulose ester such as cellulose acetate, a poly(vinyl alcohol-co-acetal) or a poly(ethylene terephthalate).
  • the support for the dye-receiving element may also be reflective such as baryta-coated paper, polyethylene-coated paper, white polyester (polyester with white pigment incorporated therein), an ivory paper, a condenser paper or a synthetic paper such as duPont Tyvek®. In a preferred embodiment, polyester with a white pigment incorporated therein is employed.
  • the dye image-receiving layer may comprise, for example, a polycarbonate, a polyurethane, a polyester, polyvinyl chloride, poly(styrene- co -acrylonitrile), poly(caprolactone) or mixtures thereof.
  • the dye image-receiving layer may be present in any amount which is effective for the intended purpose. In general, good results have been obtained at a concentration of from 1 to 5 g/m2.
  • the dye-donor elements of the invention are used to form a dye transfer image.
  • Such a process comprises imagewise-heating a dye-donor element as described above and transferring a dye image to a dye-receiving element to form the dye transfer image.
  • the dye-donor element of the invention may be used in sheet form or in a continuous roll or ribbon. If a continuous roll or ribbon is employed, it may have only the dye thereon as described above or may have alternating areas of other different dyes, such as sublimable cyan, yellow, magenta and/or black or other dyes. Such dyes are disclosed in U.S. Patent 4,541,830. Thus, one-, two-, three- or four-color elements (or higher numbers also) are included within the scope of the invention.
  • the dye-donor element comprises a poly(ethylene terephthalate) support coated with sequential repeating areas of cyan, magenta and yellow dye, at least one of the dyes being a merocyanine dye as described above, and the above process steps are sequentially performed for each color to obtain a three-color dye transfer image.
  • the process is only performed for a single color, then a monochrome dye transfer image is obtained.
  • a thermal dye transfer assemblage of the invention comprises
  • the above assemblage comprising these two elements may be preassembled as an integral unit when a monochrome image is to be obtained. This may be done by temporarily adhering the two elements together at their margins. After transfer, the dye-receiving element is then peeled apart to reveal the dye transfer image.
  • the above assemblage is formed on three occasions during the time when heat is applied by the thermal printing head. After the first dye is transferred, the elements are peeled apart. A second dye-donor element (or another area of the donor element with a different dye area) is then brought in register with the dye-receiving element and the process repeated. The third color is obtained in the same manner.
  • a yellow dye-donor element was prepared by coating the following layers in the order recited on a 6 ⁇ m poly(ethylene terephthalate) support:
  • a dye-receiving element was prepared by coating a solution of Makrolon 5705® (Bayer AG Corporation) polycarbonate resin (2.9 g/m2 in a methylene chloride and trichloroethylene solvent mixture on an ICI Melinex 990® white polyester support.
  • the dye side of the dye-donor element strip 0.75 inches (19 mm) wide was placed in contact with the dye image-receiving layer of the dye-receiver element of the same width.
  • the assemblage was fastened in the jaws of a stepper motor driven pulling device.
  • the assemblage was laid on top of a 0.55 inch (14 mm) diameter rubber roller and a TDK Thermal Head (No. L-133) and was pressed with a spring at a force of 8.0 pounds (3.6 kg) against the dye-donor element side of the assemblage pushing it against the rubber roller.
  • the imaging electronics were activated causing the pulling device to draw the assemblage between the printing head and roller at 0.123 inches/sec (3.1 mm/sec).
  • the resistive elements in the thermal print head were pulse-heated at increments from 0 to 8.3 msec to generate a graduated density test pattern.
  • the voltage supplied to the print head was approximately 22v representing approximately 1.5 watts/dot (12 mjoules/dot) for maximum power.
  • the dye-receiving element was separated from the dye-donor element and the status A blue reflection density at the maximum density was read.
  • the image was then subjected to "HID fading", 7 days, 50 Klux, 5400° K, 32°C, approximately 25% RH.
  • the percent density loss was then calculated. The following results were obtained:
  • Example 1 was repeated except that the following compounds listed in Table 2 were evaluated which do not have indoline moieties. They were compared to similar control dyes which do not have amino groups. The following results were obtained:
  • Example 1 was repeated except that the following compounds listed in Table 3 were evaluated.
  • Four control yellow dyes were prepared and tested which are similar to dyes employed in the invention except that they have a 3-methyl instead of a 3-(N,N-dialkylamino) substitution on the 2-pyrazolin-5-one ring. The following results were obtained:
  • Example 1 was repeated except that the following magenta compounds listed in Table 4 were evaluated and the Green Status A maximum density was measured.
  • Three control magenta dyes were prepared and tested which are similar to dyes employed in the invention except that they have a 3-methyl instead of a 3-(N,N-dialkylamino) substitution on the 2-pyrazolin-5-one ring. The following results were obtained:

Claims (10)

  1. Farb-Donorelement für die thermische Farbstoffübertragung mit einem Träger, auf den eine Farbstoffschicht aufgetragen ist, dadurch gekennzeichnet, daß der Farbstoff einen 3-(N-Alkyl- oder N-Aryl-amino)-2-pyrazolin-5-on-Merocyanin-farbstoff umfaßt, der in einem polymeren Binder dispergiert ist, der bei Einwirkung von Wärme durch Diffusion auf ein Farbstoff-Empfangselement übertragbar ist und praktisch keiner Photolyse unterliegt, und der an den eine Brücke bildenden Methin-Kohlenstoffatomen substituiert oder unsubstituiert ist.
  2. Element nach Anspruch 1, dadurch gekennzeichnet, daß der 3-(N-Alkyl- oder N-Aryl-amino)-2-pyrazolin-5-on-Merocyanin-Farbstoff der folgenden Formel entspricht:
    Figure imgb0020
     in der bedeuten:
    R   eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen oder eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 10 Kohlenstoffatomen;
    R¹ und R²   jeweils unabhängig voneinander Wasserstoff, wobei gilt, daß R¹ und R² nicht gleichzeitig Wasserstoff sein können; eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen oder eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 10 Kohlenstoffatomen; oder R¹ und R² gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, ein heterocyclisches Ringsystem;
    R³   gleich R;
    n   gleich 0 oder 1 und
    Z   die Atome, die zur Vervollständigung eines 5- oder 6-gliedrigen substituierten oder unsubstituierten heterocyclischen Ringes erforderlich sind.
  3. Element nach Anspruch 2, dadurch gekennzeichnet, daß Z für die Atome steht, die zur Vervollständigung eines Indolringes erforderlich sind.
  4. Element nach Anspruch 2, dadurch gekennzeichnet, daß R¹ und R² jeweils Methylgruppen sind.
  5. Element nach Anspruch 2, dadurch gekennzeichnet, daß R³ für eine Phenylgruppe steht.
  6. Element nach Anspruch 1, dadurch gekennzeichnet, daß der Träger Poly(ethylenterephthalat) umfaßt, daß die Seite des Trägers, die der Seite mit der Farbstoffschicht gegenüberliegt, mit einer Gleitschicht beschichtet ist, die ein Gleitmittel enthält und daß die Farbschicht regelmäßig angeordnete, sich wiederholende Bezirke aus blaugrünem, purpurrotem und gelbem Farbstoff aufweist.
  7. Zusammensetzung für die thermische Farbstoffübertragung mit
    a) einem Farb-Donorelement mit einem Träger, auf dem sich eine Schicht befindet, die einen in einem polymeren Binder dispergierten Farbstoff enthält und
    b) einem Farbstoff-Empfangselement mit einem Träger, auf dem sich eine Farbbild-Empfangsschicht befindet,
    wobei Farbstoff-Empfangselement und Farb-Donorelement übereinander angeordnet sind, derart, daß sich die Farbstoffschicht in Kontakt mit der Farbbild-Empfangsschicht befindet, dadurch gekennzeichnet, daß der Farbstoff einen 3-(N-Alkyl- oder N-Aryl-amino)-2-pyrazolin-5-on-Merocyanin-farbstoff umfaßt, der in einem polymeren Binder dispergiert ist, der bei Einwirkung von Wärme durch Diffusion auf ein Farbstoff-Empfangselement übertragbar ist und praktisch keiner Photolyse unterliegt, und der an den eine Brücke bildenden Methin-Kohlenstoffatomen substituiert oder unsubstituiert ist.
  8. Zusammensetzung nach Anspruch 7, dadurch gekennzeichnet, daß der 3-(N-Alkyl- oder N-Aryl-amino)-2-pyrazolin-5-on-Merocyanin-Farbstoff der folgenden Formel entspricht:
    Figure imgb0021
     in der bedeuten:
    R   eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen oder eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 10 Kohlenstoffatomen;
    R¹ und R²   jeweils unabhängig voneinander Wasserstoff, wobei gilt, daß R¹ und R² nicht gleichzeitig Wasserstoff sein können; eine substituierte oder unsubstituierte Alkylgruppe mit 1 bis 6 Kohlenstoffatomen oder eine substituierte oder unsubstituierte Arylgruppe mit 6 bis 10 Kohlenstoffatomen; oder R¹ und R² gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, ein heterocyclisches Ringsystem;
    R³   gleich R;
    n   gleich 0 oder 1 und
    Z   die Atome, die zur Vervollständigung eines 5- oder 6-gliedrigen substituierten oder unsubstituierten heterocyclischen Ringes erforderlich sind.
  9. Zusammensetzung nach Anspruch 8, dadurch gekennzeichnet, daß Z für die Atome steht, die zur Vervollständigung eines Indolringes erforderlich sind.
  10. Zusammensetzung nach Anspruch 8, dadurch gekennzeichnet, daß R¹ und R² jeweils Methylgruppen sind und daß R³ eine Phenylgruppe ist.
EP19870112145 1986-08-22 1987-08-21 N-Alkyl- oder N-Arylaminopyrazolon-merocyanin-Farbstoff-Donor-Element für die thermische Farbstoffübertragung Expired - Lifetime EP0257577B1 (de)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US06/899,273 US4705521A (en) 1986-08-22 1986-08-22 Process for reheating dye-receiving element containing stabilizer
US899273 1986-08-22
US91545186A 1986-10-06 1986-10-06
US915451 1986-10-06
US59443 1987-06-08
US07/059,443 US4743582A (en) 1986-10-06 1987-06-08 N-alkyl-or n-aryl-aminopyrazolone merocyanine dye-donor element used in thermal dye transfer

Publications (3)

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EP0257577A2 EP0257577A2 (de) 1988-03-02
EP0257577A3 EP0257577A3 (en) 1989-07-26
EP0257577B1 true EP0257577B1 (de) 1991-10-23

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EP19870112145 Expired - Lifetime EP0257577B1 (de) 1986-08-22 1987-08-21 N-Alkyl- oder N-Arylaminopyrazolon-merocyanin-Farbstoff-Donor-Element für die thermische Farbstoffübertragung

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CA (1) CA1283535C (de)
DE (1) DE3774038D1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1268942A (en) * 1986-08-22 1990-05-15 Gary W. Byers Merocyanine dye-donor element used in thermal dye transfer
EP0701907A1 (de) 1994-09-13 1996-03-20 Agfa-Gevaert N.V. Farbstoffdonorelement zur Anwendung in einem thermischen Farbstoffübertragungsverfahren
EP0733487B1 (de) 1995-01-30 2000-05-24 Agfa-Gevaert N.V. Verfahren zur Herstellung von lithographischen Druckplatte ohne Bedarf an Nassbehandlung
EP0792757B1 (de) 1996-02-27 2001-06-06 Agfa-Gevaert N.V. Farbstoffdonorelement zum Gebrauch in einem thermischen Übertragungsdruckverfahren
JP4361433B2 (ja) * 2004-07-05 2009-11-11 大日本印刷株式会社 感熱転写記録方法
ES2222851B1 (es) * 2004-10-20 2005-10-01 Saint-Gobain Calmar, S.A. Bomba con mecanismo de cierre.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4137042A (en) * 1974-05-20 1979-01-30 Ciba-Geigy Ag Dry heat process for dyeing and printing organic material which can be dyed with cationic dyes
JPS60214994A (ja) * 1984-04-11 1985-10-28 Ricoh Co Ltd 画像記録材料
US4705521A (en) * 1986-08-22 1987-11-10 Eastman Kodak Company Process for reheating dye-receiving element containing stabilizer

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EP0257577A3 (en) 1989-07-26
CA1283535C (en) 1991-04-30
EP0257577A2 (de) 1988-03-02
DE3774038D1 (de) 1991-11-28

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