EP0499099B1 - Elément récepteur pour procédé d'impression par thermosublimation - Google Patents

Elément récepteur pour procédé d'impression par thermosublimation Download PDF

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Publication number
EP0499099B1
EP0499099B1 EP19920101577 EP92101577A EP0499099B1 EP 0499099 B1 EP0499099 B1 EP 0499099B1 EP 19920101577 EP19920101577 EP 19920101577 EP 92101577 A EP92101577 A EP 92101577A EP 0499099 B1 EP0499099 B1 EP 0499099B1
Authority
EP
European Patent Office
Prior art keywords
acid
meth
weight
dye acceptor
acceptor material
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
EP19920101577
Other languages
German (de)
English (en)
Other versions
EP0499099A1 (fr
Inventor
Robert Dr. Bloodworth
Wolfgang Dr. Podszun
Heinrich Dr. Alberts
Hermann Dr. Uytterhoeven
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
Original Assignee
Agfa Gevaert AG
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Filing date
Publication date
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0499099A1 publication Critical patent/EP0499099A1/fr
Application granted granted Critical
Publication of EP0499099B1 publication Critical patent/EP0499099B1/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
    • B41M5/5254—Macromolecular coatings characterised by the use of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • 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]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]

Definitions

  • the present invention relates to a color acceptor element for thermal sublimation printing.
  • thermal sublimation printing has proven to be superior in certain requirements due to its advantages over other methods.
  • This recording method is based on the thermally induced transfer of a dye from a sheet or ribbon-shaped color donor material to a color acceptor layer and is described, for example, in "High Quality Image Recording by Sublimation Transfer Recording Material", Electronic Photography Association Documents, 27 (2), 1988 and there literature cited described in detail.
  • a particular advantage of this method is the possibility to fine-tune the color intensity.
  • 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 specifies polycarbonate, polyurethane, polyester, polyvinyl chloride, poly (styrene-co-acrylonitrile), polycaprolactone and mixtures thereof for the color acceptor layer.
  • EP-A-O 261 505 EP-A-O 275 319, EP-A-O 289 161 and EP-A-O 368 318 color acceptor layers made of copolyesters are described in detail.
  • EP-A-0 368 320 also discloses acceptor layers based on graft copolymers which contain polysiloxane segments, fluorocarbon segments or long-chain alkyl segments.
  • the color acceptor layers currently available do not yet sufficiently meet the requirements for high color density, high image stability and good resolution. It is particularly difficult to achieve high color density and sufficient image stability with minimal lateral diffusion.
  • Another difficulty is the tendency of the known receiving materials to stick to the color donor material.
  • the object of the invention is to provide a color acceptor element for the thermal sublimation printing process which does not have the disadvantages described above.
  • the task is solved by using a special graft polymer in the acceptor element.
  • the invention relates to a color acceptor material for the thermal sublimation printing process with a support and a color acceptor layer, which is characterized in that is that the color acceptor layer contains a graft polymer of an unsaturated copolyester as the graft base and a vinyl copolymer as the graft pad.
  • the graft preferably contains polymerized units of vinylaromatics and / or (meth) acrylic acid esters with 1-3 C atoms in the alcohol residue.
  • the weight ratio of graft base to graft pad is generally 10: 1 to 1: 5, preferably 5: 1 to 1: 3.
  • the unsaturated copolyester of the graft base consists of condensed residues of diols, dicarboxylic acids and optionally additionally hydroxycarboxylic acids with the proviso that 0.2 to 30 mol% of the condensed residues contain polymerizable double bonds.
  • Both aliphatic and aromatic diols can be used.
  • aliphatic diols are: Ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,2-hexanediol, 1,6-hexanediol, 1,4-cyclohexanediol, cyclohexanedimethanol- (1st , 4), 2,2'-bis (4-hydroxy-cyclohexyl) propane.
  • Diols with long alkyl chains such as 1,8-octanediol, 1,2-octanediol, 1,2-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,16-hexadecanediol, 1,20- Eicosanediol, glycerol monostearate, glycerol monolaurate and pentaerythritol distearate.
  • aromatic diols examples include: bisphenol-A, ethoxylated bisphenol-A, propoxylated bisphenol-A and p-xylylene glycol.
  • Suitable diols with polymerizable double bonds are e.g. 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, pentaerythritol diacrylate, 9-octadecene-1,12-diol and glycerol monoleate.
  • the dicarboxylic acids can be aliphatic or aromatic. Suitable aromatic dicarboxylic acids are, for example Phthalic acid, terephthalic acid, isophthalic acid, sulfoisophthalic acid, naphthalene-dicarboxylic acids and 2,2-bis (p-carboxyphenyl) propane.
  • aliphatic dicarboxylic acids include the following: malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, decanedicarboxylic acid, dodecylmalonic acid, octadecylmalonic acid, dodecylsuccinic acid, tetradecylsuccinic acid, hexadecylsuccinic acid and octadecylsuccinic acid.
  • dimer fatty acids derived from long-chain unsaturated monocarboxylic acids are also very suitable, for example the products registered under CAS Reg. Nos 68783-41-5 and 68956-10-5.
  • Dicarboxylic acids with polymerizable double bonds which are suitable for the invention are, for example, maleic acid, fumaric acid, itaconic acid, octenylsuccinic acid, isooctenylsuccinic acid, dodecenylsuccinic acid and docosenylsuccinic acid.
  • Maleic acid is preferred.
  • Suitable hydroxycarboxylic acids are, for example, 12-hydroxystearic acid, 12-hydroxy-9-octadecenoic acid and ricinoleic acid.
  • the condensed residues Preferably 5-45 mol% of the condensed residues contain one or more aromatic groups.
  • polyesters used as the graft base for the present invention can be used in various ways known condensation processes can be synthesized. Polycondensation at a high temperature in the melt is particularly suitable. Interfacial condensation can also be used.
  • the starting compounds used are not the diols and dicarboxylic acids but rather corresponding derivatives, for example epoxides or acetates instead of the diols or esters instead of the dicarboxylic acids.
  • polymerization inhibitors such as 2,5-di-tert-butylphenol
  • condensation reaction it may be expedient to add polymerization inhibitors such as 2,5-di-tert-butylphenol to the condensation reaction in order to prevent a crosslinking reaction.
  • the molecular weights of the polyesters are generally in the range from 1000 to 30,000.
  • a hydrophilizing group e.g. a carboxylate, a sulfonate, an alcoholate or a polyethylene oxide group can be incorporated into the polyester to make it water-dispersible. This can be done, for example, by using sulfoterephthalic acid, sulfoisophthalic acid or sulfoorthophthalic acid.
  • Vinyl aromatics (component a) which are suitable according to the invention are styrene, ⁇ -methylstyrene, p-methylstyrene, m-methylstyrene, p-tert-butylstyrene, p-chlorostyrene, p-chloromethylstyrene, vinylnaphthalene and vinylnaphthalene. Styrene is preferred.
  • acrylic acid esters are understood to mean methacrylic acid esters and acrylic acid esters.
  • acrylic acid esters with 1-3 C atoms in the alcohol part are methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate and isopropyl methacrylate.
  • the (meth) acrylic acid esters with 4-18 C atoms are derived from optionally substituted, aliphatic, cycloaliphatic, aromatic or mixed aromatic aliphatic alcohols.
  • the aliphatic radicals can be straight-chain as well as branched and interrupted by oxygen.
  • Suitable (meth) acrylic acid esters are: n-butyl acrylate, n-butyl methacrylate, iso-butyl acrylate, iso-butyl methacrylate, n-hexyl acrylate, n-hexyl methacrylate, ethylhexyl acrylate, ethylhexyl methacrylate, n-octyl acrylate, n-octyl methacrylate, decyl acrylate stearyl acrylate, stearyl methacrylate, Cyclohexylactylat, cyclohexyl methacrylate, 4-tert-butylcyclohexyl methacrylate, benzyl acrylate, benzyl methacrylate, phenylethyl acrylate, phenylethyl methacrylate, phenylpropyl acrylate, phenylpropyl meth
  • Mixtures of different esters can of course also be used. Mixtures which contain ethyl hexyl acrylate, decyl methacrylate, dodecyl methacrylate or phenyl ethyl acrylate are particularly suitable.
  • Mixtures of different esters can of course also be used. Mixtures which contain ethyl hexyl acrylate, decyl methacrylate, dodecyl methacrylate or phenyl ethyl acrylate are particularly suitable.
  • (meth) acrylonitrile (component b2) means both methacrylonitrile and acrylonitrile.
  • Suitable monomers are vinylidene chloride, vinyl chloride, vinyl acetate, vinyl propionate, vinyl laurate and vinyl adipate.
  • hydrophilic monomers can be used, for example, sulfoethyl methacrylate, acrylamidomethylsulfonic acid, (meth) acrylic acid, hydroxyethyl (meth) acrylate and monomers containing ethylene oxide, such as tetraethylene glycol mono (meth) acrylate.
  • the implementation of the grafting reaction is described in detail in the literature, for example in Houben-Weyl, Methods of Organic Chemistry, Volume E20 / Part 1, p. 626 ff.
  • the initiation takes place with radical formers, preferably peroxides.
  • the reaction can be carried out in a homogeneous phase as a bulk or solution polymerization or in a heterogeneous hare as an emulsion polymerization.
  • An emulsion polymerization process with sodium alkyl sulfonate as an emulsifier and potassium peroxydisulfate as an initiator is particularly suitable for the preparation of the graft polymers according to the invention.
  • Suitable substrates for the acceptor layer according to the invention are both papers, in particular also synthetic papers and polymer-coated papers, as well as films based on e.g. Polyester, polyamide, polyvinyl chloride or polycarbonate.
  • the receiving element can contain further layers known for this purpose. So it can be cheap to apply a non-stick layer over the acceptor layer.
  • a non-stick layer e.g. low and high molecular weight polysiloxanes and polysiloxane-polyether block copolymers are well suited.
  • an intermediate layer made of gelatin, for example, can be applied.
  • the graft polymers can be processed from solution or, preferably, aqueous dispersion.
  • Suitable solvents are, for example, acetone, methyl ethyl ketone, tetrahydrofuran, dioxane, ethyl acetate, dichloromethane and dimethylformamide.
  • the solution or dispersion can be applied to the support by casting or knife coating.
  • the color acceptor material according to the invention can be combined with the color donor elements customary in the thermal sublimation field. There is no tendency to bond donor and acceptor material.
  • the color images obtained are characterized by high resolution, high color saturation, high brilliance and good long-term stability.
  • a mixture of 0.400 mol dimethyl terephthalate, 0.400 mol dimethyl isophthalate, 0.150 mol dimethyl 5-sulfoisophthalate, 0.05 mol maleic acid and 1 mol 1,10-decanediol were added together with 0.0002 mol zinc acetate and 0.0001 mol antimony-III-oxide melted and stirred in a reactor under nitrogen atmosphere at 200 ° C.
  • the numerical values in the table indicate the proportion of the diol or dicarboxylic acid residues in mol%, based on the total diol or dicarboxylic acid content.
  • TPA Terephthalic acid
  • EG Ethylene glycol
  • IPA Isophthalic acid
  • DD 1,10-docanediol
  • HDD 1,2-hexadecanediol TIMES
  • Maleic acid GMO Glycerol monooleate ITAC Itaconic acid SLIDE Dianol 22 (Akzo), ethoxylated bisphenol-A OSUC Octenyl succinic acid ODSUC Octadecenylsuccinic acid DOLSUC Docosenyl succinic acid
  • the graft polymer dispersions obtained in Examples 10-30 were adjusted to a solids content of 10% with deionized water and used directly for the preparation of color-receiving layers.
  • the 10% strength graft polymer dispersions were poured onto a gelatin-coated polyethylene paper in a wet film thickness of 50 ⁇ m using a doctor blade. The coatings were dried at room temperature and then annealed at 90 ° C. for 15 minutes. The dry layer thicknesses were approximately 4.5 ⁇ m.
  • Test images were generated on the reception elements obtained using a Mitsubishi CP-100 E video printer using the Mitsubishi dye cassette CK-100 S.
  • the color intensity was determined by microdensitometry.
  • the numerical values given are the black and white densities measured on a black surface of the test image without a filter.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Laminated Bodies (AREA)
  • Graft Or Block Polymers (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Claims (6)

  1. Matériau récepteur de couleur pour le procédé de tirage par thermo-sublimation comportant un support et une couche réceptrice de couleur, caractérisé en ce que la couche acceptrice de couleur contient un polymère greffé d'un copolyester insaturé comme base de greffage et d'un copolymère vinylique comme couche greffée.
  2. Matériau récepteur de couleur selon la revendication 1, caractérisé en ce que le polyester insaturé est constitué par des restes de diols, d'acides dicarboxyliques et éventuellement d'acides hydroxycarboxyliques, 0,2 à 30 mol % des restes condensés contenant des doubles liaisons polymérisables.
  3. Matériau récepteur de couleur selon la revendication 2, caractérisé en ce que 5 à 45 mol % des restes condensés présentent un ou plusieurs groupes aromatiques.
  4. Matériau récepteur de couleur selon la revendication 1, caractérisé en ce que le copolymère vinylique est constitué par
    a) 10-80 % en poids d'hydrocarbure aromatique et/ou d'ester (méth)acrylique d'alcool en C₁-C₃,
    et
    b) 20-90 % en poids d'autres monomères vinyliques.
  5. Matériau récepteur de couleur selon la revendication 4, caractérisé en ce que le copolymère vinylique est constitué par
    a) 10-80 % en poids d'hydrocarbure vinylaromatique et/ou d'ester (méth)acrylique d'alcool en C₁ -C₃,
    et
    b1) 10-70 % en poids d'ester (méth)acrylique d'alcool en C₄-C₁₈,
    b2) 5-40 % en poids de (méth) d'acrylonitrile
    et
    b3) 0-30 % en poids d'autres monomères vinyliques.
  6. Matériau accepteur de couleur selon la revendication 5, caractérisé en ce que le composant b3 comprend des monomères hydrophiles.
EP19920101577 1991-02-13 1992-01-31 Elément récepteur pour procédé d'impression par thermosublimation Expired - Lifetime EP0499099B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914104294 DE4104294A1 (de) 1991-02-13 1991-02-13 Akzeptorelement fuer thermosublimationsdruckverfahren
DE4104294 1991-02-13

Publications (2)

Publication Number Publication Date
EP0499099A1 EP0499099A1 (fr) 1992-08-19
EP0499099B1 true EP0499099B1 (fr) 1994-12-07

Family

ID=6424924

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19920101577 Expired - Lifetime EP0499099B1 (fr) 1991-02-13 1992-01-31 Elément récepteur pour procédé d'impression par thermosublimation

Country Status (4)

Country Link
US (1) US5258355A (fr)
EP (1) EP0499099B1 (fr)
JP (1) JPH04319489A (fr)
DE (2) DE4104294A1 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992014617A1 (fr) * 1991-02-15 1992-09-03 Toyo Boseki Kabushiki Kaisha Resine colorable pour recepteur d'images par transfert du type a sublimation et recepteur d'images utilisant une telle resine
DE69410098T2 (de) 1993-08-12 1998-09-03 Eastman Chem Co Wasserdispergierbare acrylmodifizierte polyesterharze, die in überzugsmitteln verwendet werden und verfahren zu ihrer herstellung
US6375320B1 (en) 2000-03-09 2002-04-23 Eastman Kodak Company Ink jet printing method
US6759455B2 (en) * 2001-02-13 2004-07-06 Serge Magnet UV resistant resin for paraffinic solvent based paint
CN100567019C (zh) * 2004-11-24 2009-12-09 索尼株式会社 热转印用片材
DE102006009511A1 (de) * 2006-02-28 2007-08-30 Röhm Gmbh Synthese von Polyester-pfropf-Poly(meth)acrylat
EP2516173B1 (fr) 2009-12-25 2014-02-19 Kao Corporation Feuilles de réception d'image à transfert thermique
JP5571945B2 (ja) * 2009-12-25 2014-08-13 花王株式会社 熱転写受像シート用樹脂組成物
JP5624371B2 (ja) * 2010-06-04 2014-11-12 花王株式会社 熱転写受像シート用樹脂
US8648010B2 (en) 2009-12-25 2014-02-11 Kao Corporation Thermal transfer image-receiving sheets
JP5731788B2 (ja) * 2009-12-25 2015-06-10 花王株式会社 熱転写受像シート用樹脂
JP5624373B2 (ja) * 2010-06-04 2014-11-12 花王株式会社 熱転写受像シート用樹脂
JP5624375B2 (ja) * 2010-06-04 2014-11-12 花王株式会社 熱転写受像シート用樹脂
JP5607521B2 (ja) * 2010-06-04 2014-10-15 花王株式会社 熱転写受像シート用樹脂組成物の製造方法
JP5624372B2 (ja) * 2010-06-04 2014-11-12 花王株式会社 熱転写受像シート用樹脂
JP5779416B2 (ja) * 2011-06-21 2015-09-16 花王株式会社 熱転写受像シート用樹脂
JP5715511B2 (ja) * 2011-06-24 2015-05-07 花王株式会社 熱転写受像シート用樹脂の製造方法
JP5981840B2 (ja) * 2012-12-26 2016-08-31 花王株式会社 インクジェット記録用水系インク
JP2023136700A (ja) * 2022-03-17 2023-09-29 コニカミノルタ株式会社 インクジェットインク組成物、記録物、インクジェット記録方法及びインクジェット記録システム

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE68928372T2 (de) * 1988-11-10 1998-04-30 Dainippon Printing Co Ltd Bildempfangsschicht für Übertragung durch Wärme

Also Published As

Publication number Publication date
EP0499099A1 (fr) 1992-08-19
US5258355A (en) 1993-11-02
DE4104294A1 (de) 1992-08-20
DE59200868D1 (de) 1995-01-19
JPH04319489A (ja) 1992-11-10

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