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WO1995013195A1 - Support d'impression par transfert - Google Patents

Support d'impression par transfert Download PDF

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Publication number
WO1995013195A1
WO1995013195A1 PCT/US1994/011345 US9411345W WO9513195A1 WO 1995013195 A1 WO1995013195 A1 WO 1995013195A1 US 9411345 W US9411345 W US 9411345W WO 9513195 A1 WO9513195 A1 WO 9513195A1
Authority
WO
WIPO (PCT)
Prior art keywords
ink
curable
prepolymer
transfer printing
printing medium
Prior art date
Application number
PCT/US1994/011345
Other languages
English (en)
Inventor
Frank A. Meneghini
John S. Deeken
John J. Drake
Original Assignee
Markem Corporation
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Markem Corporation filed Critical Markem Corporation
Priority to KR1019960702442A priority Critical patent/KR100322459B1/ko
Priority to CA002175588A priority patent/CA2175588A1/fr
Priority to EP94930625A priority patent/EP0728073B1/fr
Priority to DE69418056T priority patent/DE69418056T2/de
Publication of WO1995013195A1 publication Critical patent/WO1995013195A1/fr

Links

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
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • B41M5/42—Intermediate, backcoat, or covering layers
    • 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
    • B41M5/38207—Contact thermal transfer or sublimation processes characterised by aspects not provided for in groups B41M5/385 - B41M5/395
    • 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
    • B41M5/392—Additives, other than colour forming substances, dyes or pigments, e.g. sensitisers, transfer promoting agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
    • B41M7/009—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using thermal means, e.g. infrared radiation, heat
    • 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
    • B41M5/40—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography
    • B41M5/46—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used characterised by the base backcoat, intermediate, or covering layers, e.g. for thermal transfer dye-donor or dye-receiver sheets; Heat, radiation filtering or absorbing means or layers; combined with other image registration layers or compositions; Special originals for reproduction by thermography characterised by the light-to-heat converting means; characterised by the heat or radiation filtering or absorbing means or layers
    • B41M5/465—Infrared radiation-absorbing materials, e.g. dyes, metals, silicates, C black

Definitions

  • TRANSFER PRINTING MEDIUM Background of the Invention This invention relates to laser-induced transfer printing.
  • irradiation of an ink-bearing carrier with laser light causes the ink to transfer from the carrier to a surface, e.g., the surface of a microelectronic device, audio cassette, computer diskette, or syringe body.
  • a surface e.g., the surface of a microelectronic device, audio cassette, computer diskette, or syringe body.
  • the invention features a transfer printing medium that includes a carrier to which is applied a curable laser-transferrable ink having one or more layers.
  • the transfer medium is capable of converting laser energy to heat.
  • the ink includes (a) at least one colorant; (b) at least one polymerization initiator; and (c) at least one curable prepolymer.
  • colorant it is meant any additive that imparts color to the ink, including the colors white and black. Colorants include both dyes and pigments, as well as metallized coatings.
  • prepolymer it is meant any species capable of being polymerized following either thermal or photochemical initiation to form a polymer.
  • the ink transfers to a surface of interest and cures in one step upon application of laser energy.
  • at least one of the polymerization initiators is a thermal polymerization initiator and at least one of the prepolymers is thermally curable.
  • at least one of the polymerization initiators is a photoinitiator and at least one of the prepolymers is photochemically curable.
  • One example of a preferred prepolymer is an epoxy- functionalized prepolymer.
  • a second example is an epoxy- functionalized prepolymer combined with a vinyl ether- functionalized prepolymer.
  • a third example is an epoxy- functionalized prepolymer combined with an acrylate- functionalized prepolymer.
  • a fourth example includes the acrylate-functionalized prepolymers themselves.
  • a fifth example is a blocked isocyanate-functionalized prepolymer and a sixth example is a blend of a vinyl ether- functionalized prepolymer and a maleate- or maleimide- functionalized prepolymer.
  • At least one of the ink layers may be a curable size coat that includes a polymerization initiator and a curable prepolymer.
  • the size coat is used in combination with a color coat layer.
  • the color coat is non-curable and includes a colorant and a thermoplastic film-forming resin.
  • the color coat is curable and includes a colorant, a polymerization initiator, and a curable prepolymer.
  • the polymerization initiators and prepolymers found in the respective layers may be the same as, or different from, each other.
  • the invention features a laser-induced transfer printing method using the above- described transfer printing medium.
  • the method includes the steps of irradiating the particular transfer printing medium with laser light of a predetermined wavelength to transfer the ink from the carrier to a surface of interest, and curing the ink to adhere the ink to the surface of interest.
  • the transfer and cure of the ink may be effected in a single step through irradiation with said laser light. Cure may also be effected in a separate step subsequent to transfer.
  • the invention provides transfer printing media featuring curable inks that adhere well to the surface on which they are deposited following laser irradiation.
  • the inks transfer cleanly from the supporting carrier and cure rapidly; in some cases, transfer and cure are effected in a single step. It is not necessary to add a separate self-oxidizing material such as nitrocellulose in order to effect transfer.
  • a separate self-oxidizing material such as nitrocellulose in order to effect transfer.
  • the ability to use non-curable layers (e.g., non-curable color coats) in combination with curable layers (e.g., curable size coats) expands the types of materials that can be used for the inks, enabling the properties of the inks to be adjusted as needed for a particular application.
  • the invention features a transfer printing medium capable of converting laser energy to heat in which a curable laser-transferrable ink having one or more layers is deposited on a carrier.
  • the carrier must have suf iciently low surface energy to permit transfer of the ink. It also must not melt or otherwise deform upon laser irradiation.
  • suitable carriers include flexible plastic films such as polyethylene, polypropylene, and polyester.
  • the transfer medium is capable of converting laser energy to heat to promote transfer of the ink from the carrier to the surface of interest.
  • one or more thermal convertors are incorporated into the carrier, the ink, or both.
  • the thermal convertors may be separate additives or may be part of the prepolymer.
  • the amount of convertor ranges from about 0.25 to about 30% by weight (based upon the total solids content of the ink) .
  • the particular convertor is selected based upon the particular laser energy used for irradiation.
  • the preferred convertors are carbon black, polyethylene glycol (e.g., PEG 3000 commercially available from Union Carbide) , talc (e.g., Nytal 400 commercially available from R.T. Vanderbilt) , and PPZ, a phosphotriazine commercially available from Idemitsu Petrochemicals Co. Ltd; PPZ may also function as a prepolymer.
  • the preferred convertors are IR99, IRA 980, and IR165, all of which are proprietary dyes commercially available from Glendale Protective Technologies, IR dye 14,617 (a proprietary dye commercially available from Eastman Kodak) , and Projet 900NP (a proprietary dye commercially available from ICI) .
  • the preferred convertors are IR dye 14,617 and IRA 980.
  • the inks may have one or more layers, with particular ingredients (e.g., prepolymer, polymerization initiator, etc.) being present in any of the layers.
  • a one layer ink referred to here as a "one-pass” coating
  • a curable color coat that includes, in a single layer, a curable prepolymer, a polymerization initiator, and a colorant.
  • a two layer ink referred to here as a "two- pass” coating
  • a color coat which may be curable or non-curable
  • the inks are curable, adhesion upon transfer to a surface of interest is improved.
  • the advantage of the size coat (which is transferred with the color coat upon laser irradiation) is that adhesion is further enhanced, thereby making it possible to use even a non-curable color coat.
  • the inks contain one or more curable prepolymers, with the total amount of curable prepolymer ranging from 25 to 95% by weight (based upon the total solids content of the ink) .
  • Curable prepolymers useful in the invention have two or more functional groups available for crosslinking (which occurs either simultaneously with transfer upon application of laser radiation or following laser irradiation in a separate thermal or photochemical cure step) .
  • One class of suitable curable prepolymers includes epoxy-functionalized prepolymers such as bisphenol A diglycidyl ether (commercially available from Shell Oil under the designation Epon 1001) and epoxy-functionalized novolac resins (e.g., Epon 164 commercially available from Shell Oil) .
  • Epon 1001 bisphenol A diglycidyl ether
  • Epon 164 commercially available from Shell Oil
  • Lower molecular epoxides such as
  • UVR6110 (a liquid diepoxide commercially available from Union Carbide) may be added as well.
  • a second class of suitable curable prepolymers includes these epoxy-functionalized prepolymers in combination with one or more vinyl ether-functionalized prepolymers which co-cure with the epoxy-functionalized prepolymers.
  • suitable vinyl ether- functionalized prepolymers include bisphenol A-divinyl ether adduct; 2,4-toluene diisocyanate/hydroxybutyl vinyl ether adduct; cyclohexyl divinyl ether commercially available from GAF or ISI Products; vinyl ethyl ether, vinyl isobutyl ether, vinyl octadecyl ether, polyethylene glycol divinyl ether, polytetrahydrofuran/350/divinyl ether, and trimethylol propane trivinyl ether, all of which are commercially available from BASF; Rapi/cure divinyl ether/3, Rapi/cure cyclohexyl vinyl ether, Rapi/cure PEPC, and Rapi/
  • a third class of suitable curable prepolymers includes the above-described epoxy-functionalized prepolymers in combination with one or more acrylate- functionalized prepolymers.
  • acrylate- functionalized prepolymers include RDX 29522 and Ebecryl 639 (both of which are commercially available from Radcure) ; Sartomer 351 (commercially available from Sartomer) ; and NR440 (commercially available from Zeneca Resins) .
  • a fourth class of suitable curable prepolymers includes the acrylate-functionalized prepolymers themselves without the epoxy-functionalized prepolymers.
  • a fifth class of suitable curable prepolymers includes blocked isocyanate-functionalized prepolymers.
  • Examples include B1299 (commercially available from Huls) and BL4165A (commercially available from Miles) .
  • a sixth class of suitable curable prepolymers includes the above-described vinyl ether-functionalized prepolymers in combination with maleate- or maleimide- functionalized prepolymers.
  • maleate- functionalized prepolymers include 89-8902 (commercially available from Cargil Products) ; and Astrocure 78HV and Astrocure 78LV (both of which are commercially available from Zircon) .
  • maleimide-functionalized prepolymers include BMI/S/M/20/TDA (commercially available from Mitsui Toatsu Chemical, Inc.
  • Non-curable layers may be used in combination with one or more curable layers.
  • a non-curable color coat may be combined with an overlying curable size coat.
  • Suitable non-curable resins are thermoplastic film-forming resins. Examples include acrylic resins such as Rhoplex B85 (an acrylic dispersion commercially available from Rohm & Haas) and Amsco 3011 (an acrylic dispersion available from Rohm & Haas) ; urethane resins such as QW-16 (a urethane dispersion useful as a film-former that is commercially available from K.J. Quinn) ; phenoxy resins such as PKH 35 (commercially available from Union Carbide) ; and combinations thereof.
  • the amount of non-curable prepolymer in the ink ranges from about 15 to about 35% by weight (based upon the total solids content of the ink) .
  • the inks also contain a polymerization initiator in an amount ranging from about 0.1 to 5% by weight (based upon the total solids content of the ink) .
  • the initiator (which typically is a free radical or cationic initiator) may be a photochemical initiator or a thermal initiator; in some cases, the same initiator can act as both a thermal and a photochemical initiator.
  • layers containing photochemical initiators may be combined with layers containing thermal initiators.
  • some initiators may be used in conjunction with accelerators such as benzpinacole, copper II salts (e.g., copper benzoate) , and hexaphenylethane.
  • thermal initiators In the case of thermal initiators, the initiator must exhibit good stability at ambient temperature to prevent premature curing of the prepolymer. In addition, the initiation temperature must be within the range achievable by laser irradiation.
  • suitable thermal initiators for cationic initiation include aryl sulfonium salts (e.g., the salts described in O90/11303, hereby incorporated by reference) ; aryl iodonium salts (e.g., UVE 9310 and U 479, both of which are commercially available from General Electric) ; and ammonium salts
  • thermal initiators for free radical initiation include the class of compounds leading to peroxy radicals, e.g., hydroperoxides, peroxyesters, and peroxyketals; representative compounds are commercially available from Elf-Atochem. Also suitable for free radical initiation are azo polymerization initiators commercially available from Wako.
  • the initiator In the case of photochemical initiators, the initiator must also exhibit good stability at ambient temperature to prevent premature curing of the prepolymer. In addition, it must exhibit absorption maxima in regions of the electromagnetic spectrum different from the regions in which the colorant exhibits absorption maxima.
  • suitable photochemical initiators for cationic initiation include aryl sulfonium salts (e.g., UNI 6974 commercially available from Union Carbide) and aryl iodonium salts (e.g., UNE 9310 and U 479, both of which are commercially available from General Electric) .
  • Another example of a suitable initiator for cationic initiation is hydroxy naphthyl imide sulfonate ester.
  • Suitable photochemical initiators for free radical initiation include CPTX and ITX (both commercially available from Ciba-Geigy) , each of which is combined with methyl diethanolamine (commercially available from Aldrich Chemical Co.; lucerin TPO (commercially available from BASF) combined with methyl diethanolamine; Darcure 4265 (commercially available from Ciba Geigy) , and Irgacure 369 combined with ITX.
  • the ink contains one or more colorants, which may be dyes, pigments, or metallized coatings (e.g., an aluminized coating) .
  • the colorant is present in an amount ranging from about 35 to 65% by weight (based upon the total solids content of the ink) .
  • the particular colorant is chosen based upon the color desired on the final printed surface.
  • Suitable colorants include pigments such as talc, Ti0 2 (white) , phthalogreen (GT-674-D) , chrome green oxide (6099) , ultramarine blue (RS-9) , black oxide (BK- 5099D) , Kroma red (7097), and Novaperm yellow (HR-70) , and dyes such as dynonicidine (2915) and Dianell orange, as well as the aforementioned metallized coatings.
  • a sensitizer may be added in an amount ranging from about 0.5 to 8% by weight (based upon the total solids content of the ink) to extend the irradiating wavelength for photoinitiation into the visible region.
  • sensitizers are useful, for example, where the formulation contains large amounts of Ti0 2 pigment which absorbs light below 400 nm and thus competes with the initiator.
  • suitable sensitizers include perylene, rubrene, phenothiazine, anthracene derivatives, and thioxanthones, as well as lucerin TPO (commercially available from BASF) .
  • ingredients which may be added to the inks to improve the coatability, printability, print performance, and durability of the inks include various surfactants, dispersing agents, and polymer dispersions. The amount of each ingredient is selected based upon the desired properties.
  • suitable surfactants which may be anionic, cationic, or nonionic
  • suitable surfactants include Triton X-100 (an aryl ethoxylate commercially available from Rohm & Haas) and FC 430 (a fluoroaliphatic polymeric ester available from 3M)
  • suitable dispersing agents include polyacrylate salts such as Daxad 30, a 30% aqueous solution of polysodiumacrylate commercially available from W.R. Grace.
  • suitable dispersions include Shamrock 375 and Aquacer 355, both of which are polyethylene wax dispersions commercially available from Diamond Shamrock.
  • the transfer medium according to the invention is prepared by combining the ink ingredients in an aqueous or organic solvent (with aqueous solvents being preferred) , and then applying the resulting composition to the carrier. If a size coat is used, it is applied on top of the color coat. To facilitate coating, the total solids content of the ink is adjusted to be between 10 and 50% by weight of the ink.
  • the coated carrier is then irradiated with laser light (e.g., as described in the commonly assigned et al. application, U.S.
  • Suitable lasers include C0 2 lasers (irradiation wavelength equals 10.6 ⁇ m), Nd:YAG lasers (irradiation wavelength equals 1.06 ⁇ m), and diode lasers (irradiation wavelength equals, e.g., 0.9 ⁇ m) .
  • the particular irradiation wavelength, power, and time of application parameters are selected to ensure clean transfer.
  • This example describes the preparation of a transfer medium having one-pass, thermally curable, cationically initiated, ink.
  • Example 2 Water was added to adjust the total solids content to 35% by weight, after which the resulting ink was coated onto a 1.2 mil thick polypropylene carrier film using a #15 mayer rod. The coated surface of the film was then placed in intimate contact with the surface of a molded semiconductor device. Next, a C0 2 laser was directed through the uncoated side of the carrier film to transfer the ink to the surface of the semiconductor device. The laser dwelled on each addressed pixel for 16 ⁇ sec. The power output of the laser at the point of contact with the coated film was 14.5 W. The device bearing the transferred image was then placed in a forced hot air oven for 30 min. at 175°C to cure the ink. After curing, the transferred image was found to be resistant to treatment with 1,1,1-trichloroethane (3 min. soak, 10 brush strokes, cycled 3 times) .
  • 1,1,1-trichloroethane 3 min. soak, 10 brush strokes, cycled 3 times
  • This example describes the preparation of a transfer medium having a two-pass, cationically initiated ink in which both the color coat and the size coat are photochemically curable.
  • Triaryl sulfonium salt-based initiator commercially available from Union Carbide. Water was added to adjust the total solids content to 35% by weight, after which the resulting color coat was applied to a 1.2 mil thick polypropylene carrier film using a #13 mayer rod.
  • Methyl ethyl ketone was added to adjust the total solids content of the size coat to 25% by weight, after which the resulting size coat was applied on top of the color coat using a #5 mayer rod.
  • the coated surface of the film was then placed in intimate contact with the surface of a molded semiconductor device.
  • a C0 2 laser was directed through the uncoated side of the carrier film to transfer the ink (color coat plus size coat) to the surface of the semiconductor device.
  • the laser dwelled on each addressed pixel for 20 ⁇ sec.
  • the power output of the laser at the point of contact with the coated film was 14.5 W.
  • the device bearing the transferred image was then cured (5 min. at a 150°C preheat, followed by a 3.6 sec exposure to UV radiation) .
  • the resulting cured printed image was found to be resistant to treatment with 1,1,1-trichloroethane (3 min. soak, 10 brush strokes, cycled 3 times) .
  • This example describes the preparation of a transfer medium having a two-pass, cationically curable ink in which the color coat is non-curable and the size coat is thermally curable.
  • UVR 6110 2 11.6 FC-430 3 3.0
  • This example describes the preparation of a transfer medium having a one-pass, thermally curable, cationically initiated ink in which transfer and cure takes place in a single step upon laser irradiation.
  • Methyl ethyl ketone was added to adjust the total solids content to 50% by weight, after which the resulting ink was coated onto a 1.2 mil thick polypropylene carrier film using a #10 mayer rod. The coated surface of the film was then placed in intimate contact with a glass slide. Next, a C0 2 laser was directed through the uncoated side of the carrier film to transfer the ink to the surface of the glass slide. The laser dwelled on each addressed pixel for 80 ⁇ sec. After addressing, the transferred coating was removed form the glass slide and analyzed by differential scanning calorimetry. There was no evidence of residual heat of reaction, indicating that the transferred coating had cured during the transfer step.
  • Example 5 Example 5
  • This example describes the preparation of a transfer medium having a two-pass, free radical-initiated ink in which both the color coat and the size coat are photochemically curable.
  • Photochemical free radical initiator commercially available from Ciba Geigy. Water was added to adjust the total solids content of the size coat to 40% by weight, after which the resulting size coat was applied on top of the color coat using a #5 mayer rod.
  • the coated surface of the film was then placed in intimate contact with the surface of a molded semiconductor device.
  • a C0 2 laser was directed through the uncoated side of the carrier film to transfer the ink (color coat plus size coat) to the surface of the semiconductor device.
  • the laser dwelled on each addressed pixel for 20 ⁇ sec.
  • the power output of the laser at the point of contact with the coated film was 14.5 W.
  • the device bearing the transferred image was then cured (5 min. at a 100°C preheat, followed by passage through a UV fusion oven equipped with an H bulb at a speed of 100 in./min.).
  • the resulting cured printed image was found to be resistant to treatment with 1,1,1- trichloroethane (3 min. soak, 10 brush strokes, cycled 3 times) .

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Thermal Sciences (AREA)
  • Toxicology (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
  • Laminated Bodies (AREA)
  • Paper (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

L'invention se rapporte à un support d'impression par transfert comprenant une base sur laquelle on a appliqué une encre qui peut être durcie et transférée par laser, et qui est dotée d'une ou de plusieurs couches. Le support de transfert peut convertir l'énergie laser en chaleur. L'encre comprend: (a) au moins un colorant; (b) au moins un initiateur de polymérisation; et (c) au moins un prépolymère qui peut être durci.
PCT/US1994/011345 1993-11-09 1994-10-06 Support d'impression par transfert WO1995013195A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
KR1019960702442A KR100322459B1 (ko) 1993-11-09 1994-10-06 전사인쇄매체
CA002175588A CA2175588A1 (fr) 1993-11-09 1994-10-06 Support d'impression par transfert
EP94930625A EP0728073B1 (fr) 1993-11-09 1994-10-06 Support d'impression par transfert
DE69418056T DE69418056T2 (de) 1993-11-09 1994-10-06 Übertragungsdruckmaterial

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US14928593A 1993-11-09 1993-11-09
US08/149,285 1993-11-09

Publications (1)

Publication Number Publication Date
WO1995013195A1 true WO1995013195A1 (fr) 1995-05-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/011345 WO1995013195A1 (fr) 1993-11-09 1994-10-06 Support d'impression par transfert

Country Status (7)

Country Link
EP (1) EP0728073B1 (fr)
JP (1) JPH07232480A (fr)
KR (1) KR100322459B1 (fr)
AT (1) ATE179125T1 (fr)
CA (1) CA2175588A1 (fr)
DE (1) DE69418056T2 (fr)
WO (1) WO1995013195A1 (fr)

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WO1996024495A1 (fr) * 1995-02-10 1996-08-15 Klaus Kall Procede permettant de recouvrir une plaque de base transparente et plaque de base transparente pourvue d'un revetement, obtenue selon ledit procede
EP0799713A1 (fr) * 1996-04-03 1997-10-08 Minnesota Mining And Manufacturing Company Elément donneur pour transfert thermique contenant un composé sublimable incolore et procédé pour former des images
WO1997038865A1 (fr) * 1996-04-15 1997-10-23 Minnesota Mining And Manufacturing Company Element d'imagerie par transfert thermique a adressage laser avec intercouche
EP0795421A3 (fr) * 1996-03-14 1998-03-18 Minnesota Mining And Manufacturing Company Elément d'enregistrement des images par transfert thermique adressé par laser et méthode d'enregistrement des images
US5843617A (en) * 1996-08-20 1998-12-01 Minnesota Mining & Manufacturing Company Thermal bleaching of infrared dyes
EP0871573A4 (fr) * 1995-12-06 1998-12-09
WO1999016625A1 (fr) * 1997-09-08 1999-04-08 Thermark, Llc Procede de marquage par laser
EP0924096A1 (fr) * 1997-12-18 1999-06-23 Matsushita Electric Industrial Co., Ltd Procédé de marquage utilisant des rayons actiniques et produit moulé marqué par ce procédé
US5998085A (en) * 1996-07-23 1999-12-07 3M Innovative Properties Process for preparing high resolution emissive arrays and corresponding articles
WO2000044960A1 (fr) * 1999-01-27 2000-08-03 The United States Of America, As Represented By The Secretary Of The Navy Gravure directe par evaporation par laser pulse assistee par matrice
US6177151B1 (en) * 1999-01-27 2001-01-23 The United States Of America As Represented By The Secretary Of The Navy Matrix assisted pulsed laser evaporation direct write
WO2001017793A1 (fr) * 1999-09-09 2001-03-15 3M Innovative Properties Company Element de transfert thermique avec une couche de transfert contenant un plastifiant, et processus de transfert thermique
US6238847B1 (en) 1997-10-16 2001-05-29 Dmc Degussa Metals Catalysts Cerdec Ag Laser marking method and apparatus
EP1052104A3 (fr) * 1995-12-06 2001-08-22 Markem Corporation Marquage de pièces par balayage
WO2002064377A1 (fr) * 2001-02-09 2002-08-22 3M Innovative Properties Company Compositions pouvant etre transferees par voie thermique et procedes
US6503310B1 (en) 1999-06-22 2003-01-07 Dmc2 Degussa Metals Catalysts Cerdec Ag Laser marking compositions and method
US6503316B1 (en) 2000-09-22 2003-01-07 Dmc2 Degussa Metals Catalysts Cerdec Ag Bismuth-containing laser markable compositions and methods of making and using same
US6852948B1 (en) 1997-09-08 2005-02-08 Thermark, Llc High contrast surface marking using irradiation of electrostatically applied marking materials
WO2007059853A1 (fr) 2005-11-22 2007-05-31 Merck Patent Gmbh Procede de transfert thermique d'un film a cristaux liquides a l'aide d'un element de transfert
US7238396B2 (en) 2002-08-02 2007-07-03 Rieck Albert S Methods for vitrescent marking
WO2007062785A3 (fr) * 2005-11-30 2007-07-26 Merck Patent Gmbh Transfert laser d'elements caracteristiques de securite
US7396631B2 (en) 2005-10-07 2008-07-08 3M Innovative Properties Company Radiation curable thermal transfer elements
US7534543B2 (en) 1996-04-15 2009-05-19 3M Innovative Properties Company Texture control of thin film layers prepared via laser induced thermal imaging
US7678526B2 (en) 2005-10-07 2010-03-16 3M Innovative Properties Company Radiation curable thermal transfer elements
US9744559B2 (en) 2014-05-27 2017-08-29 Paul W Harrison High contrast surface marking using nanoparticle materials
US11613803B2 (en) 2018-05-09 2023-03-28 Lpkf Laser & Electronics Ag Use of a component in a composition, composition for laser transfer printing, and laser transfer printing method

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3715991A1 (de) * 1986-05-14 1987-11-19 Mitsubishi Paper Mills Ltd Aufzeichnungsmaterial und aufzeichnungsverfahren
JPH03244588A (ja) * 1990-02-22 1991-10-31 Canon Inc 転写記録媒体

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3715991A1 (de) * 1986-05-14 1987-11-19 Mitsubishi Paper Mills Ltd Aufzeichnungsmaterial und aufzeichnungsverfahren
JPH03244588A (ja) * 1990-02-22 1991-10-31 Canon Inc 転写記録媒体

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 16, no. 36 (M - 1205) 29 January 1992 (1992-01-29) *

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EP1052104A3 (fr) * 1995-12-06 2001-08-22 Markem Corporation Marquage de pièces par balayage
EP0871573A4 (fr) * 1995-12-06 1998-12-09
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US6852948B1 (en) 1997-09-08 2005-02-08 Thermark, Llc High contrast surface marking using irradiation of electrostatically applied marking materials
WO1999016625A1 (fr) * 1997-09-08 1999-04-08 Thermark, Llc Procede de marquage par laser
US6313436B1 (en) * 1997-09-08 2001-11-06 Thermark, Llc High contrast surface marking using metal oxides
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US6238847B1 (en) 1997-10-16 2001-05-29 Dmc Degussa Metals Catalysts Cerdec Ag Laser marking method and apparatus
US6245397B1 (en) 1997-12-18 2001-06-12 Matsushita Electric Industrial Co., Ltd. Marking method and marked molding
EP0924096A1 (fr) * 1997-12-18 1999-06-23 Matsushita Electric Industrial Co., Ltd Procédé de marquage utilisant des rayons actiniques et produit moulé marqué par ce procédé
US6766764B1 (en) 1999-01-27 2004-07-27 The United States Of America As Represented By The Secretary Of The Navy Matrix assisted pulsed laser evaporation direct write
US6177151B1 (en) * 1999-01-27 2001-01-23 The United States Of America As Represented By The Secretary Of The Navy Matrix assisted pulsed laser evaporation direct write
WO2000044960A1 (fr) * 1999-01-27 2000-08-03 The United States Of America, As Represented By The Secretary Of The Navy Gravure directe par evaporation par laser pulse assistee par matrice
US6503310B1 (en) 1999-06-22 2003-01-07 Dmc2 Degussa Metals Catalysts Cerdec Ag Laser marking compositions and method
US6228543B1 (en) 1999-09-09 2001-05-08 3M Innovative Properties Company Thermal transfer with a plasticizer-containing transfer layer
WO2001017793A1 (fr) * 1999-09-09 2001-03-15 3M Innovative Properties Company Element de transfert thermique avec une couche de transfert contenant un plastifiant, et processus de transfert thermique
US6680121B2 (en) 2000-09-22 2004-01-20 Dmc2 Degussa Metals Catalysts Cerdec Ag Bismuth-containing laser markable compositions and methods of making and using same
US6503316B1 (en) 2000-09-22 2003-01-07 Dmc2 Degussa Metals Catalysts Cerdec Ag Bismuth-containing laser markable compositions and methods of making and using same
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WO2002064377A1 (fr) * 2001-02-09 2002-08-22 3M Innovative Properties Company Compositions pouvant etre transferees par voie thermique et procedes
US7238396B2 (en) 2002-08-02 2007-07-03 Rieck Albert S Methods for vitrescent marking
US7396631B2 (en) 2005-10-07 2008-07-08 3M Innovative Properties Company Radiation curable thermal transfer elements
US7678526B2 (en) 2005-10-07 2010-03-16 3M Innovative Properties Company Radiation curable thermal transfer elements
WO2007059853A1 (fr) 2005-11-22 2007-05-31 Merck Patent Gmbh Procede de transfert thermique d'un film a cristaux liquides a l'aide d'un element de transfert
WO2007062785A3 (fr) * 2005-11-30 2007-07-26 Merck Patent Gmbh Transfert laser d'elements caracteristiques de securite
US9744559B2 (en) 2014-05-27 2017-08-29 Paul W Harrison High contrast surface marking using nanoparticle materials
US11613803B2 (en) 2018-05-09 2023-03-28 Lpkf Laser & Electronics Ag Use of a component in a composition, composition for laser transfer printing, and laser transfer printing method

Also Published As

Publication number Publication date
EP0728073A1 (fr) 1996-08-28
ATE179125T1 (de) 1999-05-15
EP0728073B1 (fr) 1999-04-21
KR960705689A (ko) 1996-11-08
DE69418056T2 (de) 1999-11-11
KR100322459B1 (ko) 2002-10-04
CA2175588A1 (fr) 1995-05-18
JPH07232480A (ja) 1995-09-05
DE69418056D1 (de) 1999-05-27

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