EP0481200B1 - Elément récepteur de colorant pour un procédé d'impression par sublimation par la chaleur - Google Patents

Elément récepteur de colorant pour un procédé d'impression par sublimation par la chaleur Download PDF

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Publication number
EP0481200B1
EP0481200B1 EP19910114420 EP91114420A EP0481200B1 EP 0481200 B1 EP0481200 B1 EP 0481200B1 EP 19910114420 EP19910114420 EP 19910114420 EP 91114420 A EP91114420 A EP 91114420A EP 0481200 B1 EP0481200 B1 EP 0481200B1
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EP
European Patent Office
Prior art keywords
acid
dye
polyester
acceptor element
layer
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
EP19910114420
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German (de)
English (en)
Other versions
EP0481200A1 (fr
Inventor
Rolf Dr. Wehrmann
Hermann Dr. Uytterhoeven
Richard Dr. Weider
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.)
Agfa Gevaert AG
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Agfa Gevaert AG
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Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Priority to US07/773,036 priority Critical patent/US5250494A/en
Priority to JP3296629A priority patent/JPH04263991A/ja
Publication of EP0481200A1 publication Critical patent/EP0481200A1/fr
Application granted granted Critical
Publication of EP0481200B1 publication Critical patent/EP0481200B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • B41M5/50—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
    • B41M5/5263—Macromolecular coatings characterised by the use of polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • B41M5/5272—Polyesters; Polycarbonates

Definitions

  • the present invention relates to a color acceptor element for the thermal sublimation printing process.
  • thermo sublimation printing process There are a number of methods for printing out video or computer-stored images, of which the thermal sublimation printing process has proven to be superior in certain requirements due to its advantages over other processes.
  • a sheet-like or ribbon-shaped donor material which contains a dye capable of sublimation is brought into contact with a dye (dye) acceptor layer and heated imagewise to transfer the dye.
  • the thermal head is controlled and the dye is transferred from the donor material to the acceptor element in accordance with the stored template.
  • a detailed description of the process can be found, for example, in "High Quality Image Recording by Sublimation Transfer Recording Material", Electronic Photography Association Documents 27 (2), 1988, and the literature cited therein.
  • a particular advantage of this printing process is the ability to fine-tune color intensities.
  • Color acceptor elements for thermal sublimation printing usually include a backing, e.g. Paper or transparent films that are coated with the actual color acceptor layer.
  • An adhesive layer can be applied between the base and the acceptor layer.
  • (Co) polyester is a commonly used binder. They are obtained by the reaction of one or more dicarboxylic acids with one or more diols. At least one dicarboxylic acid and / or a diol preferably contains aromatic groups so that the glass transition temperature Tg of the polycondensate is at least 0 ° C., preferably at least 10 ° C.
  • Such polyesters are e.g. described in EP-A 0 289 161, EP-A-0 275 319, EP-A 0 261 505, EP-A 0 368 318, JP 86/3796 or JP 269 589.
  • the color acceptor layers currently available do not yet sufficiently meet the requirements for high color density, sufficient image stability and good resolution. It is particularly difficult to achieve high color density and sufficient image stability with minimal lateral diffusion. Furthermore, sticking between the donor ribbon and the acceptor element can occur during the printing process, which leads to blurred images. Therefore, sliding layers or lubricants are often used.
  • the object of the invention was to provide a color acceptor element for the thermal sublimation printing process which does not have the disadvantages mentioned above.
  • the object is achieved by using a special polymer in the color acceptor element.
  • a color acceptor element for the thermal sublimation printing process has now been found, which has very high dyeability, very good sliding properties and good image stability and is based on a specially constructed polyester.
  • the present invention relates to a dye acceptor element for the thermal sublimation printing process with a layer support and an ink acceptor layer thereon, which contains a polyester formed from diols and dicarboxylic acids, characterized in that 0.5 to 60 mol% of the diol component of the polyester consists of a dimer diol.
  • Dimer diols are optionally a saturated, unsaturated or aromatic carbocyclic ring-containing dialkyl-substituted diols with 24 or more carbon atoms, which can be obtained by hydrogenation from so-called dimer fatty acids ("dimer acids").
  • dimerization products from unsaturated aliphatic carboxylic acids (fatty acids) with 12 or more carbon atoms, preferably from unsaturated C18 fatty acids such as oleic acid and linoleic acid. Dimer acids are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A8, p. 535. They are generally present as a mixture.
  • Suitable dimer diols can be described, for example, as mixtures of compounds of the general formulas I, II and III wherein R1 and R2 are alkyl and R3 and R4 are alkylene, with the proviso that R1, R2, R3 and R4 together in formula I 40, 36, 32, 28, 24 or 20 carbon atoms and in formulas II and III contain 36, 32, 28, 24, 20 or 16 carbon atoms.
  • Such diols can be obtained, for example, from unsaturated C22 fatty acids (upper corner value) or unsaturated C12 fatty acids (lower corner value). C16 and C18 fatty acids are preferably used.
  • Such product mixtures are available, for example, from Unichema GmbH, Emmerich, under the product name Pripol® 2033.
  • the polyesters according to the invention can be prepared by condensation reactions of one or more dicarboxylic acids with one or more diols, including dicarboxylic acids and diols containing aromatic groups and the dimer diols.
  • Derivatives of the acids - for example esters, acid chlorides etc. - and diols - for example acetates - can also be used for the condensation.
  • dicarboxylic acids examples include oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, 1,10-decanedicarboxylic acid, 1,11-undecanedicarboxylic acid, 1,12-dodecanedicarboxylic acid, 1,13-tridecanedicarboxylic acid, 1,14-tetradecanedicarboxylic acid, etc.
  • cyclohexanedicarboxylic acid maleic acid, maleic anhydride, fumaric acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, toluenedicarboxylic acids, naphthalenedicarboxylic acids, sulfoisophthalic acid, and in particular non-substituted alkyl or dicarboxylic acids 5-C alkenyl acids in the main chain between the carboxyl groups and at least 6 carbon atoms in a side chain.
  • Examples of the last-mentioned alkyl or alkenyl-substituted dicarboxylic acids are Tetradecylmalonklare, hexadecylmalonic, Octadecylmalonklare, Diheptylmalonklare, octylsuccinic acid, Decylbernsteinklare, dodecylsuccinic acid, Tetradecylbernsteinklandre, Hexadecylbernsteinklare, octadecylsuccinic acid, octenylsuccinic acid, isooctenylsuccinic, Decenylbernsteinklare, dodecenylsuccinic acid, tetradecenylsuccinic acid, hexadecenylsuccinic acid, octadecenylsuccinic acid, Docosylbernsteinklad, Docosenylbernstein Acid
  • hexadecylmalonic acid octadecylmalonic acid
  • hexadecylsuccinic acid hexadecylsuccinic acid
  • docosenylsuccinic acid are particularly preferred.
  • diols ethylene glycol, diethylene glycol, triethylene glycol, neopentyl glycol, 1,4-butanediol, 1,2-propanediol, 1,3-propanediol, 1,6-hexanediol, 1,2-hexanediol, 1,4-cyclohexanediol, 1,4 -Cyclohexanedimethanol, ethoxylated or propoxylated bisphenols such as Dianol® 22 (ethoxylated BPA, Akzo), Dianol® 33 (propoxylated BPA, Akzo) or ethoxylated or propoxylated hydroquinone.
  • Dianol® 22 ethoxylated BPA, Akzo
  • Dianol® 33 propoxylated BPA, Akzo
  • Long-chain diols such as 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol can also be used, and in particular those provided with at least one side chain short-chain diols containing no more than 5 carbon atoms between the two hydroxyl groups and an alkyl or alkenyl radical with at least 6 carbon atoms in the side chain.
  • the long chain alkyl or alkenyl radical of the side chain can be connected to the main chain directly or via links such as aromatic groups, cycloaliphatic groups or heteroatoms (for example -O-, -NH-, -O-CO-, -NH-CO-).
  • Examples of the last-mentioned short-chain diols provided with a side chain are 1,2-octanediol, 1,2-decanediol, 1,2-dodecanediol, 1,2-hexadecanediol, 1,4-octadecanediol, N, N-di- (n -decyl) -amino-2,3-propanediol, glycerol and pentaerythritol partial esters such as glycerol monostearate, glycerol monooleate, glycerol monorizin oleate, glycerol monolaurate, glycerol monocaprylate, pentaerythritol distearate and pentadecylresorcinol.
  • 1,2-dodecanediol 1,2-hexadecanediol, glycerol monostearate, glycerol monooleate and pentaerythritol distearate are particularly preferred.
  • the polyester according to the invention formed from dicarboxylic acids and diols can additionally contain built-in residues of hydroxyalkanecarboxylic acids, in particular those which contain a side chain with preferably at least 8 carbon atoms.
  • Suitable examples are hydroxybutyric acid, hydroxydecanoic acid, hydroxydodecanoic acid, hydroxyhexadecanoic acid, hydroxyoctadecanoic acid, methyl-n-hexylglycolic acid, 2,3-dihydroxynonanoic acid, 11-hydroxyundecanoic acid, 2-hydroxy-4,6,6-trimethylheptanoic acid, 16-hydroxyhexadecanoic acid, 12-hydroxyadadanoic acid, 12-hydroxy-9-octadecenoic acid (ricinoleic acid), 12,13-ethoxy-9-octadecenoic acid.
  • the proportion of dimer diol is between 0.5 and 60, preferably between 1 and 30, particularly preferably between 1.5 and 20 mol% of the total diol components.
  • the polyesters according to the invention have molecular weights between 500 and 20,000, preferably between 750 and 15,000, particularly preferably between 1000 and 12,000, each determined by gel permeation chromatography using polystyrene as standard.
  • hydrophilic (polar) groups such as sulfonic acid groups (example: sulfoisophthalic acid)
  • polar solvents or solvent mixtures such as water, water / ethanol or water / MEK
  • the color acceptor layer can e.g. pigments or mixtures of several pigments, such as e.g. Titanium dioxide, zinc oxide, kaolin, clay, calcium carbonate or Aerosil can be added.
  • pigments or mixtures of several pigments such as e.g. Titanium dioxide, zinc oxide, kaolin, clay, calcium carbonate or Aerosil can be added.
  • additives such as UV absorbers, light stabilizers or antioxidants, can be added if necessary.
  • the color acceptor layers of the present invention can contain a lubricant to improve the sliding properties, primarily between the donor and acceptor elements.
  • a lubricant to improve the sliding properties, primarily between the donor and acceptor elements.
  • solid waxes such as polyethylene wax, amidic waxes or Teflon® powder can be used, but also optionally fluorine-containing surfactants, paraffin, silicone or fluorine-containing oils or silicone-containing copolymers such as polysiloxane-polyether copolymers. Reactive, modified silicones can also be used.
  • Such products can contain carboxyl, amino and / or epoxy groups and, with a suitable combination of e.g. Amino and epoxy silicone lead to cross-linked sliding layers.
  • the lubricant mentioned can also be applied as a separate coating, as a dispersion or, if appropriate, from a suitable solvent as a "top coat".
  • the thickness of such a layer is then preferably 0.01 to 5 ⁇ m, particularly preferably between 0.05 and 2 ⁇ m.
  • Various materials can be used as carriers for the color acceptor layers. It is possible to use transparent films such as polyethylene terephthalate, polycarbonate, polyether sulfone, polyolefin, polyvinyl chloride, polystyrene, cellulose or polyvinyl alcohol copolymer films. Of course, reflective documents such as the most varied types of paper such as polyolefin-coated paper or pigmented papers are also used. Also laminates made from the above materials are applicable. Typical combinations are laminates of cellulose paper and synthetic paper or cellulose paper and polymer films or polymer films and synthetic paper or other combinations.
  • the carriers ensure the necessary mechanical stability of the color acceptor element. If the color acceptor layer has sufficient mechanical stability, an additional support can be dispensed with.
  • the color acceptor layers of the present invention preferably have total layer thicknesses of 0.3 to 50 ⁇ m, particularly preferably 0.5 to 10 ⁇ m, if a carrier of the type described above is used or if this is dispensed with, from 3 to 120 ⁇ m.
  • the color acceptor layer can consist of a single layer, but two or more layers can also be applied to the support. When using transparent supports, a double-sided coating can be applied to increase the color intensity, e.g. in the European patent application (EP-A-452 566).
  • the color acceptor element of the present invention may also include various intermediate layers between the backing and the dye-receiving layer.
  • the intermediate layer can act as a resilient element (elastic layer), as a barrier layer for the transferred one Dye or as an adhesive layer depending on the specific application.
  • suitable materials are urethane, acrylate or olefin resins, but also butadiene rubbers or epoxies.
  • the thickness of this intermediate layer is usually between about 1 to 2 and 20 microns.
  • Diffusion barrier layers have the task of preventing the transferred dyes from diffusing into the support. Materials that fulfill this task can be soluble in water or in organic solvents or in mixtures, but preferably in water. Suitable materials are, for example, gelatin, polyacrylic acid, maleic anhydride copolymers, polyvinyl alcohol or cellulose acetate.
  • the optional additional layers such as elastic layer, diffusion barrier layer, adhesive layer etc. as well as the actual color acceptor layer can e.g. Contain silicate, clay, aluminum silicate, calcium carbonate, calcium sulfate, barium sulfate, titanium dioxide, aluminum oxide powder.
  • the color acceptor element of the present invention can also be antistatically treated on the front or back in the usual way.
  • the color acceptor layers containing the polyester resins according to the invention are usually produced from solution.
  • Suitable solvents are, for example, water, methyl ethyl ketone (MEK), butyl acetate, acetone, alcohols or solvent mixtures, such as MEK / water, ethanol / water.
  • MEK methyl ethyl ketone
  • the solution can be applied to the carrier by pouring or knife coating.
  • the color acceptor element according to the invention is suitable for producing dye transfer images.
  • a color acceptor element is brought into contact with a color donor element on the coating side and the latter is imagewise heated from the rear.
  • the dye transfer is brought about by heating to approximately 400 ° C. for a few milliseconds.
  • the dye donor layer is usually heated imagewise by means of a commercially available thermal head in a thermal sublimation printer.
  • the thermal energy required for dye transfer can also be supplied by laser light, IR flash exposure or by means of a heated pen, if necessary the dye layer or another layer contains the donor element means that absorb light and convert it into heat, for example, soot.
  • the imagewise heating can also be effected using the known resistive ribbon technology.
  • the carrier of the donor element is, for example, a ribbon-shaped polycarbonate layer loaded with soot and coated with a thin aluminum film, to which electrical current is supplied by electrical control of a print head electrode (print head electrode), as a result of which heat is generated in the resistive ribbon. Since the printhead electrode hardly heats itself up, this technology has an advantageous effect on the printing speed.
  • a multicolor picture can be made by successively bringing the color acceptor element according to the invention into contact with each of three or more donor elements with different dyes, by imagewise heating the donor element from the latter to receive an imagewise dye transfer in the relevant color and then separating it from that.
  • the color acceptor element according to the invention can be made by successively bringing the color acceptor element according to the invention into contact with each of three or more donor elements with different dyes, by imagewise heating the donor element from the latter to receive an imagewise dye transfer in the relevant color and then separating it from that.
  • the color acceptor element and / or donor element can be provided with optically recognizable markings.
  • the color images obtained with the color acceptor element according to the invention are notable for high resolution, high color densities, high brilliance and good long-term stability.
  • polyester resins according to the invention are produced in a conventional condensation apparatus under common reaction conditions.
  • the final condensation takes place over 2 hours at 280 ° C with an oil pump vacuum.
  • the resin is isolated by pouring out the melt.
  • the excess ethanediol corresponding to the stoichiometry indicated above is removed by distillation in the course of the condensation, so that almost equivalent molar amounts of acid and alcohol groups are present.
  • the polyester resins 1-6 were dissolved in water / MEK (8: 2) in accordance with the concentration given in Table 1 and poured onto a paper using a doctor blade in a wet film thickness of 20 ⁇ m or 25 ⁇ m (see Table 1) which was coated on both sides with polyethylene and on one side of which a gelatin layer had additionally been applied over the polyethylene.
  • the polyester solution was applied to this side.
  • the coatings were dried in a forced-air drying cabinet at 70 ° C. for 30 minutes. Each sample (a) was left uncoated (no sliding layer).
  • a 0.5% solution in ethanol from Tego® Glide 410 (Tego Chemie Service GmbH) with a wet film thickness of 24 ⁇ m was applied to each further sample (b) and dried at 70 ° C. in a forced-air drying cabinet.
  • Test images were generated on the dye-receiving elements obtained using a Mitsubishi CP-100 E video printer using the Mitsubishi dye cassette CK-100 S.
  • the dye acceptor layers which are built up from the polyesters according to the invention, are distinguished by very high color densities and greatly reduced tendency to stick.
  • Table 2 lists the color densities, which were determined using a Macbeth RD 919 densitometer, and the adhesive behavior.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Laminated Bodies (AREA)

Claims (4)

  1. Elément acceptant les couleurs pour le procédé d'impression par thermosublimation, comprenant un support de couche et une couche acceptant les couleurs qui se trouve sur cette dernière et qui contient un polyester formé à partir de diols et d'acides dicarboxyliques, caractérisé en ce que de 0,5 à 60 moles % du composant de diol du polyester sont constitués par un ou plusieurs diols dialkylsubstitués comprenant 24 atomes de carbone ou plus et contenant éventuellement un noyau saturé, non saturé ou aromatique.
  2. Elément acceptant les couleurs selon la revendication 1, caractérisé en ce que le polyester est formé à partir d'acides dicarboxyliques aromatiques.
  3. Elément acceptant les couleurs selon la revendication 2, caractérisé en ce que, comme acide dicarboxylique aromatique, on utilise l'acide téréphtalique, l'acide isophtalique et/ou l'acide sulfo-isophtalique éventuellement sous forme d'un dérivé (sel, chlorure d'acide, ester) et en ce que, comme diol (en dehors du diol dimère), on utilise l'éthylèneglycol.
  4. Elément acceptant les couleurs selon l'une quelconque des revendications 1 à 3, caractérisé en ce que le polyester contient des groupes conférant de la solubilité.
EP19910114420 1990-10-17 1991-08-28 Elément récepteur de colorant pour un procédé d'impression par sublimation par la chaleur Expired - Lifetime EP0481200B1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US07/773,036 US5250494A (en) 1990-10-17 1991-10-08 Dye acceptor element for the thermal sublimation printing process
JP3296629A JPH04263991A (ja) 1990-10-17 1991-10-17 熱昇華焼き付け方法用染料受容体要素

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP90202759 1990-10-17
EP19900202759 EP0481129B1 (fr) 1990-10-17 1990-10-17 Elément récepteur pour le transfert de colorant par thermosublimation

Publications (2)

Publication Number Publication Date
EP0481200A1 EP0481200A1 (fr) 1992-04-22
EP0481200B1 true EP0481200B1 (fr) 1993-11-24

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP19900202759 Expired - Lifetime EP0481129B1 (fr) 1990-10-17 1990-10-17 Elément récepteur pour le transfert de colorant par thermosublimation
EP19910114420 Expired - Lifetime EP0481200B1 (fr) 1990-10-17 1991-08-28 Elément récepteur de colorant pour un procédé d'impression par sublimation par la chaleur

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP19900202759 Expired - Lifetime EP0481129B1 (fr) 1990-10-17 1990-10-17 Elément récepteur pour le transfert de colorant par thermosublimation

Country Status (3)

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EP (2) EP0481129B1 (fr)
JP (1) JP2623181B2 (fr)
DE (2) DE69009057T2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0526645B1 (fr) * 1991-02-15 1997-11-05 Toyo Boseki Kabushiki Kaisha Resine colorable pour recepteur d'images par transfert du type a sublimation et recepteur d'images utilisant une telle resine
EP0627662B1 (fr) * 1993-05-24 1999-07-07 Agfa-Gevaert N.V. Matériau photographique comprenant un support en copolyester
TW558522B (en) * 2001-07-30 2003-10-21 Kiwa Chemical Ind Co Ltd Laminated body for printing with temporary display layer and printing method using the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8709798D0 (en) * 1987-04-24 1987-05-28 Ici Plc Receiver sheet
EP0364900B1 (fr) * 1988-10-17 1996-07-31 Dai Nippon Insatsu Kabushiki Kaisha Procédé pour l'enregistrement par transfer thermique.

Also Published As

Publication number Publication date
EP0481200A1 (fr) 1992-04-22
DE69009057D1 (de) 1994-06-23
EP0481129A1 (fr) 1992-04-22
DE59100636D1 (de) 1994-01-05
JP2623181B2 (ja) 1997-06-25
EP0481129B1 (fr) 1994-05-18
DE69009057T2 (de) 1994-11-10
JPH04282293A (ja) 1992-10-07

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