EP0498245B1 - Support récepteur de colorant pour le procédé d'impression par thermosublimation - Google Patents

Support récepteur de colorant pour le procédé d'impression par thermosublimation Download PDF

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Publication number
EP0498245B1
EP0498245B1 EP92101233A EP92101233A EP0498245B1 EP 0498245 B1 EP0498245 B1 EP 0498245B1 EP 92101233 A EP92101233 A EP 92101233A EP 92101233 A EP92101233 A EP 92101233A EP 0498245 B1 EP0498245 B1 EP 0498245B1
Authority
EP
European Patent Office
Prior art keywords
polyether
bis
color
layer
weight
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
EP92101233A
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German (de)
English (en)
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EP0498245A1 (fr
Inventor
Rolf Wehrmann
Herbert Hugl
Dittmar Nerger
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 of EP0498245A1 publication Critical patent/EP0498245A1/fr
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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
    • 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
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate

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 foils that are coated with the actual color acceptor layer.
  • An adhesive layer can be applied between the base and the acceptor layer.
  • Polymers from different substance classes can be used as the material for the color acceptor layer.
  • US-A-4 705 522 discloses polycarbonate, polyurethane, polyester, polyvinyl chloride, poly (styrene-co-acrylonitrile), polycaprolactone and mixtures thereof for the color acceptor layer.
  • EP-A-0 228 066 describes a color acceptor layer with improved light stability, which contains a mixture of polycaprolactone or a linear aliphatic polyester with poly (styrene-co-acrylonitrile) and / or bisphenol-A polycarbonate.
  • EP-A-0 227 094 describes a color acceptor element based on bisphenol A polycarbonate which can be processed into layers with a particularly low surface roughness at a molecular weight of the polycarbonate of greater than 25,000. From US-A-4 927 803 a polycarbonate receiving layer is known in which the polycarbonate is built up from bisphenol-A and non-aromatic diols.
  • the color acceptor layers currently available do not yet sufficiently meet the requirements for high color density, adequate image stability and good resolution. It is particularly difficult to make big ones To achieve color density and sufficient image stability with minimal lateral diffusion.
  • 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, in which a polyether carbonate (PEC) is used in the color acceptor layer, optionally in a mixture with other suitable partners.
  • PEC polyether carbonate
  • the invention relates to a dye acceptor element for the thermal sublimation printing process with a support and a dye acceptor layer thereon, consisting essentially of polycarbonate, characterized in that the polycarbonate contains 30 to 95% by weight of aromatic carbonate structural units of the formula I.
  • [-O-diphen-O-CO-] (I) wherein diphen is the rest of a diphenol having 6 to 30, preferably 12 to 24, carbon atoms and contains 70 to 5% by weight of aliphatic polyether carbonate structural units of the formula II, [-O-polyether-O-CO-] (II) wherein polyether represents the remainder of an aliphatic polyether diol with a molecular weight Mn of 600 to 20,000, preferably of 4,000 to 10,000, where up to about 8% by weight, preferably up to about 4% by weight, of the diphenol portion can be replaced by C2-C15 alkylene diols and / or C5 or C6 cycloalkylene diols, and optionally up to about 20 mol% of the carbonate groups -O-CO-O- can be replaced by aromatic and / or (cyclo) -aliphatic dicarboxylate groups.
  • the polymers used according to the invention in the color acceptor layer are segmented, aliphatic-aromatic polyether copolycarbonates with a molecular weight M w (weight average) from 20,000 to 350,000, preferably 100,000 to 250,000 (determined according to the light scattering method with the scattered light photometer).
  • a part, up to about 20 mol%, preferably up to about 10 mol% of the carbonate groups -O-CO-O- by terephthalate and / or isophthalate groups and / or a part, up to about 10 mol%, preferably up to about 5 mol% of the carbonate groups can be replaced by C2-C15 alkylene dicarboxylate groups and / or C5 or C6 cycloalkylene dicarboxylate groups.
  • segmented, aliphatic-aromatic polyether copolycarbonates are known (see, for example, DE-A-2 251 066, US-A-4 160 791, US-A-4 075 108 and US-A-4 069 151).
  • they can be made from diphenols using the phase interface method HO-Phen-OH (III), Polyether diphenol carbonates HO-phen-O-CO-O-polyether-O-CO-O-phen-OH and phosgene can be prepared in a known manner (see. DE-A-34 08 804).
  • the corresponding part of the diphenols HO-phen-OH can be replaced by the C2-C15-alkylene diols or the C5- or Co-cycloalkylene diols and used in the form of their bischlorocarbonic acid esters; a corresponding part of the phosgene can also be replaced by terephthalic acid dichloride, isophthalic acid dichloride and / or the C2-C15 alkanedicarboxylic acid dichlorides or C calculating.- or C6-cycloalkanedicarboxylic acid dichlorides.
  • monophenols or aromatic monocarboxylic acid chlorides can be used in the usual amounts in a known manner.
  • the polyether copolycarbonates can be linear or branched in a known manner, for example by incorporating triphenols.
  • Diphenols (III) suitable according to the invention are, for example, bis (hydroxyphenyl) alkanes, bis (hydroxyphenyl) cycloalkanes and dicycloalkanes, dihydroxydiphenyls, bis (hydroxyphenyl) ethers, bis (hydroxyphenyl) sulfones, Bis (hydroxyphenyl) sulfides, bis (hydroxyphenyl) ketones, ⁇ , ⁇ -bis (hydroxyphenyl) diisopropylbenzenes and their alkylated compounds.
  • diphenols (III) examples include 4,4'-dihydroxydiphenyl, 2,4′-dihydroxydiphenyl, 4,4'-dihydroxy-3,3 ', 5,5'-tetramethyldiphenyl, 4,4'-dihydroxy-3,3'-dimethyldiphenyl, Bis (4-hydroxyphenyl) methane, Bis (4-hydroxy-3,5-dimethylphenyl) methane, Bis (4-hydroxyphenyl) ethane, 2,2-bis (4-hydroxyphenyl) propane (“bisphenol A”), 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 1,1-bis (4-hydroxy-3,5-dimethylphenyl) cyclohexane, Bis (4-hydroxyphenyl) oxide, Bis (4-hydroxy-3,5-dimethylphenyl) oxide, Bis (4-hydroxyphenyl) oxide
  • 2,2-bis (4-hydroxyphenyl) propane (“bisphenol A")
  • 2,2-bis (hydroxy-3,5-dimethylphenyl) propane is particularly preferred.
  • Aliphatic polyether diols suitable for the preparation of the polyether diphenol carbonates are preferably polyethylene glycols, such as those from Union Cabide (Carbowax), British Petrol (Breox), Hoechst (Polyglycol) and Hüls (Polywachs) with molecular weights (number average molecular weights) of 600 to 20,000, are preferred 4,000 to 10,000.
  • polyethylene glycols mentioned other hydroxyl-containing polyethers, e.g. Polyethylene oxide / propylene oxide mixed and block polyethers are used.
  • C2-C15 alkylene diols are, for example, ethylene glycol, 1,2-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,12-dodecanediol and 1,2-dihydroxidodecane; a suitable one Cycloalkylene diol is, for example, 1,4-dihydroxycyclohexane;
  • C2-C15 alkanedicarboxylic acid dichlorides are, for example, succinic acid dichloride, adipic acid dichloride, azelaic acid dichloride, sebacic acid dichloride and dodecanedicarboxylic acid dichloride;
  • Suitable cycloalkanedicarboxylic acid dichlorides are, for example, hexahydroterephthaloyl chloride and hexahydro-isophthaloyl chloride.
  • Suitable phenolic chain terminators are all customary phenols, such as phenol itself, p-tert-butylphenol and p-di-tert-octylphenol, and monofunctional polyethers, and benzoic acid chloride and alkylbenzoic acid chloride as aromatic monocarboxylic acid chlorides.
  • Preferred ratios of aromatic carbonate structural units (I) to aliphatic polyether carbonate structural units (II) are 30% by weight to 55% by weight (I) to 70% by weight to 45% by weight (II), since here the water-spreading effect is also available without the addition of surfactants.
  • the polyether copolycarbonates to be used according to the invention have relative solution viscosities (measured on solutions of 0.5 g in 100 ml of methylene chloride at 25 ° C.) between 1.1 and 3.8, preferably between 1.5 and 3.8.
  • the molecular weights M n (number average) of the polyether diols are determined by gel permeation chromatography and hydroxyl number.
  • EP-A-0 227 094 EP-A-0 228 066, EP-A-0 133 011, EP-A-0 133 012 or EP-A-0 144 247.
  • High-boiling solvents or plasticizers can also be added to the color acceptor layer. For example, you can ensure better solubility of the transferred dyes.
  • Useful representatives of these compounds are e.g. cited in JP 62/174 754, JP 62/245 253, JP 61/209 444, JP 61/200 538, JP 62/136 646, JP 62/30 274.
  • 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 e.g. UV absorbers, light stabilizers or antioxidants can be added.
  • the color acceptor layers of the present invention may 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, if appropriate, fluorine-containing surfactants, paraffin, silicone or fluorine-containing oils or silicone-containing copolymers such as polysiloxane polyether copolymers.
  • 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 Use polyethylene terephthalate, polycarbonate, polyether sulfone, polyolefin, polyvinyl chloride, polystyrene, cellulose or polyvinyl alcohol copolymer films. Of course, there are also reflective documents such as the most varied types of paper such as Polyolefin-coated paper or pigmented papers are used. Laminates made from the above materials can also be used. 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. described in European patent application 90 200 930.7.
  • 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 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 ⁇ m.
  • Diffusion barrier layers have the task of preventing the diffusion of the transferred dyes into the support. Materials which 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 image acceptor element of the present invention can also be antistatically equipped on the front or back in the usual way. It can also be provided with markings, preferably on the back of the carrier, in order to achieve precise positioning during the printing process.
  • the color acceptor element according to the invention can be combined with the color donor elements customary in the field of thermal sublimation printing.
  • the polyether carbonate from Example 1 used to construct the color acceptor element according to the invention is sold commercially by Bayer AG under the name KU 3013.
  • the other polyether carbonates can be produced on a larger scale in an analogous manner.
  • the color images obtained in a thermal sublimation printer are characterized by high resolution, high color densities, high brilliance and good long-term stability.
  • the color acceptor layers containing polyether carbonate are usually produced from solution.
  • Suitable solvents are, for example, methylene chloride, chlorobenzene, THF or dioxolane.
  • the solution can be applied to the support by pouring or knife coating.
  • polyether carbonates corresponding to the parts by weight given in Table 1 are prepared from polyethylene oxide and bisphenol A and phosgene (excess).
  • the procedure here is that bisphenol A, polyether and sodium hydroxide solution are initially introduced in a methylene chloride / water mixture and then phosgene is introduced with an excess of 150 mol%, based on bisphenol A. At the same time, so much sodium hydroxide solution is metered in that a pH of 14 is kept constant.
  • copolycondensates obtained in Examples 1 to 3 were used to build up color acceptor layers as follows:
  • the color acceptor layers which are composed of the polyether carbonates according to the invention are distinguished by increased color densities and greatly reduced tendency to stick.
  • Table 2 shows color densities, which were determined using a Macbeth RD 919 densitometer for the pure yellow field of the test image, and the adhesive behavior.
  • Examples 1 to 3 show that the color acceptor layers built up from the modified polycarbonates have higher color layers and have better adhesive properties (less sticking).

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

Claims (1)

  1. Elément récepteur de couleur pour le procédé d'impression par thermosublimation comprenant un support sur lequel se trouve une couche de récepteur de couleur principalement constituée de polycarbonate, caractérisé en ce que le polycarbonate contient 30 à 95 % en poids de motifs structuraux carbonate aromatiques de formule I

            [ -O-Diphén-O-CO-]   (I)

       dans laquelle Diphén représente le reste d'un diphénol ayant 6 à 30, de préférence 12 à 24 atomes de carbone,
       et 70 à 5 % en poids de motifs structuraux polyéther-carbonate aliphatiques de formule II

            [ -O-Polyéther-O-CO- ]   (II)

       dans laquelle Polyéther représente le reste d'un polyéther-diol aliphatique ayant un poids moléculaire Mn de 600 à 20 000,
       le cas échéant, une proportion allant jusqu'à environ 8 % en poids du diphénol pouvant être remplacée par des alkylène-diols en C₂ à C₁₅ et/ou des cycloalkylène-diols en C₅ ou C₆,
       et, le cas échéant, une proportion allant jusqu'à environ 20 moles % des groupes carbonate -O-CO-O- pouvant être remplacés par des groupes dicarboxylate aromatiques et/ou (cyclo)-aliphatiques.
EP92101233A 1991-02-07 1992-01-27 Support récepteur de colorant pour le procédé d'impression par thermosublimation Expired - Lifetime EP0498245B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4103680 1991-02-07
DE4103680A DE4103680A1 (de) 1991-02-07 1991-02-07 Farbakzeptorelement fuer das thermosublimationsdruckverfahren

Publications (2)

Publication Number Publication Date
EP0498245A1 EP0498245A1 (fr) 1992-08-12
EP0498245B1 true EP0498245B1 (fr) 1994-08-17

Family

ID=6424555

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92101233A Expired - Lifetime EP0498245B1 (fr) 1991-02-07 1992-01-27 Support récepteur de colorant pour le procédé d'impression par thermosublimation

Country Status (4)

Country Link
US (1) US5273952A (fr)
EP (1) EP0498245B1 (fr)
JP (1) JPH04319488A (fr)
DE (2) DE4103680A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5262378A (en) * 1992-12-23 1993-11-16 Eastman Kodak Company Thermal dye transfer receiving element with miscible polycarbonate blends for dye image-receiving layer

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA991776A (en) * 1971-10-18 1976-06-22 Robert E. Kesting Integral (unskinned) high void volume polycarbonate membranes and a dry process for forming same
US3945926A (en) * 1971-10-18 1976-03-23 Chemical Systems, Inc. Integral microporous high void volume polycarbonate membranes and a dry process for forming same
US4160791A (en) * 1974-03-26 1979-07-10 The United States Of America As Represented By The Secretary Of The Department Of Health, Education And Welfare Polycarbonate membranes and production thereof
US4075108A (en) * 1974-03-26 1978-02-21 The United States Of America As Represented By The Department Of Health, Education And Welfare Polycarbonate membranes and production thereof
US4069151A (en) * 1976-03-31 1978-01-17 C. R. Bard, Inc. Thin polycarbonate membranes for use in hemodialysis
DE3408804A1 (de) * 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen Polyether-copolycarbonate fuer dialysemembranen
US4695286A (en) * 1985-12-24 1987-09-22 Eastman Kodak Company High molecular weight polycarbonate receiving layer used in thermal dye transfer
US4740497A (en) * 1985-12-24 1988-04-26 Eastman Kodak Company Polymeric mixture for dye-receiving element used in thermal dye transfer
US4705522A (en) * 1986-08-22 1987-11-10 Eastman Kodak Company Alkolxy derivative stabilizers for dye-receiving element used in thermal dye transfer
US4927803A (en) * 1989-04-28 1990-05-22 Eastman Kodak Company Thermal dye transfer receiving layer of polycarbonate with nonaromatic diol

Also Published As

Publication number Publication date
DE4103680A1 (de) 1992-08-13
JPH04319488A (ja) 1992-11-10
EP0498245A1 (fr) 1992-08-12
US5273952A (en) 1993-12-28
DE59200376D1 (de) 1994-09-22

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