WO1993012939A1 - Thermal transfer imaging with infrared laser and azamethine dyes - Google Patents
Thermal transfer imaging with infrared laser and azamethine dyes Download PDFInfo
- Publication number
- WO1993012939A1 WO1993012939A1 PCT/US1992/010554 US9210554W WO9312939A1 WO 1993012939 A1 WO1993012939 A1 WO 1993012939A1 US 9210554 W US9210554 W US 9210554W WO 9312939 A1 WO9312939 A1 WO 9312939A1
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- Prior art keywords
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- unsubstituted
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- carbon atoms
- hydrogen
- Prior art date
Links
- 239000000975 dye Substances 0.000 title description 23
- 238000003384 imaging method Methods 0.000 title description 5
- 239000003086 colorant Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 20
- -1 alkyoxyl Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000011358 absorbing material Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000001931 thermography Methods 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 239000004615 ingredient Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 229920004142 LEXAN™ Polymers 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- MSSQDESMUMSQEN-UHFFFAOYSA-N 1-amino-2-bromo-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(Br)=C2N MSSQDESMUMSQEN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 1
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical compound C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 description 1
- ATXPWKWYLDEURI-UHFFFAOYSA-N 1-amino-4-(ethylamino)-9,10-dioxoanthracene-2-carbonitrile Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C#N)C=C2NCC ATXPWKWYLDEURI-UHFFFAOYSA-N 0.000 description 1
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- FDTLQXNAPKJJAM-UHFFFAOYSA-N 2-(3-hydroxyquinolin-2-yl)indene-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C1=NC2=CC=CC=C2C=C1O FDTLQXNAPKJJAM-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000004775 Tyvek Substances 0.000 description 1
- 229920000690 Tyvek Polymers 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
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- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- PSQIRYDALVAXHN-UHFFFAOYSA-N n-[2-[[1,3-bis(dicyanomethylidene)inden-2-ylidene]amino]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=C1C(=C(C#N)C#N)C2=CC=CC=C2C1=C(C#N)C#N PSQIRYDALVAXHN-UHFFFAOYSA-N 0.000 description 1
- DWLYVZBCVVCNGX-UHFFFAOYSA-N n-[2-[[1,3-bis(dicyanomethylidene)inden-2-ylidene]amino]-5-(dipropylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CCC)CCC)=CC=C1N=C1C(=C(C#N)C#N)C2=CC=CC=C2C1=C(C#N)C#N DWLYVZBCVVCNGX-UHFFFAOYSA-N 0.000 description 1
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- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000006100 radiation absorber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/40—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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/382—Contact thermal transfer or sublimation processes
- B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
-
- 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
-
- 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
Definitions
- This invention relates to thermal imaging. More particularly this invention relates to donor elements for laser-induced thermal imaging processes in which the donor element contains certain infra-red absorbing azamethine compounds.
- Thermal imaging processes are well-known.
- a donor element comprising a colorant is heated, by, for example, a thermal head or an infra-red laser, causing the colorant to be transferred to a receptor sheet.
- the colorant may be a dye or pigment or a mixture of dyes and/or pigments.
- Imagewise heating of the donor element reproduces the corresponding image on the receptor sheet.
- Transfer in register to the same receptor sheet from several differently colored donor elements produces a multicolored image.
- Different single colored donor elements or a multicolor donor element carrying different colors in different regions which can be brought into position in turn can be used for transfer.
- an infra-red laser is used for thermal transfer, only a single, small, selected area is heated at one time. Since only a small region of colorant is heated and transferred, the image can be built up pixel by pixel.
- Computer control of such processes allows multicolor images of high definition to be produced at high speed. This process is disclosed in Baldock, UK Patent 2,083,726.
- the donor element comprises a heat transferable dye, sometimes called a thermal transfer dye, usually in a formulation with a binder, supported on a substrate.
- the dye donor element is contacted with a receptor sheet, and the surface of the substrate irradiated with an infra-red laser to transfer the dye to the receptor sheet.
- a dye which strongly absorbs the wavelength of the exciting laser is required for the heat transferable dye to be directly heated by the laser. This need to match the infra-red absorption of the dye to the emission of the laser greatly restricts the number of dyes which can be used in the laser-induced thermal transfer process.
- the dye may be heated indirectly by incorporating a separate radiation absorber, such as carbon black., into the dye layer.
- carbon black has a tendency to aggregate or agglomerate when coated so that the absorber is not uniformly distributed in the donor element.
- small carbon black particles tend to be carried over with the dye, contaminating the image.
- an infra-red absorbing compound can be added to the dye layer.
- Dye donor layers containing infra-red absorbing materials have been disclosed by, for example, Barlow, U.S. Patent 4,778,128; DeBoer, EPO Application 0 321 923 and U.S. Patent 4,942,141; and Kellogg, U.S. Patent 5,019,549.
- infra-red absorbing materials which may be used to advantage in laser-induced thermal transfer processes.
- This invention is a donor element for a laser- induced thermal transfer process, said donor element comprising a support bearing thereon a colorant layer, said colorant layer comprising a colorant and an infra ⁇ red absorbing material, said infra-red absorbing material having the following structure:
- Ri, R2, R 3 , and R 4 are each independently hydrogen; substituted or unsubstituted alkyl, acyl, alkyoxyl, aryloxyl, acyloxyl, acylamido, alkylamino, arylamino, or sulfonyl containing 1 to 8 carbon atoms; halogen; cyano; or substituted or unsubstituted phenyl; or (Ri and R 2 ) , (R 2 and R 3 ) , or (R 3 and R 4 ) are joined to form a five-, six-, or seven-membered substituted or unsubstituted aliphatic, aromatic, or heteroaromatic ring; R 5 , Rg, R 7 , and R 8 are each independently hydrogen; substituted or unsubstituted alkyl, acyl, alkyoxyl, aryloxyl, acyloxyl, acylamido, alkylamino, arylamino,
- the invention is a donor element for thermal transfer processes particularly adapted for use in laser-induced thermal transfer imaging.
- the donor element comprises a colorant layer and a support.
- the colorant layer comprises a heat-transferable colorant, an infra-red absorbing material, and, preferably, a binder.
- the infra-red absorbing material must have a strong absorption in the emission region of the exciting laser and should have good thermal stability so that it is not decomposed by the incident radiation.
- the material is preferably substantially non-transferable so it is not transferred during imaging. It is preferred that it be essentially non-absorbing in the visible so that small amounts, if transferred, will not affect the image. It is also preferred that the material be soluble in a solvent which can be used to coat the colorant layer onto the support.
- Infra-red absorbing materials of Formula I (supra) as defined are used in the colorant layer.
- Ri * * 2r ⁇ -3r and R 4 are each independently chosen from a number of groups, provided the presence of the group or groups does not adversely affect the properties of the infra-red absorbing material required for the operation of the invention. These properties include, for example, chemical stability, thermal stability, solubility, and absorption spectrum.
- ⁇ -lr ⁇ -2r ⁇ - 3 r and R 4 may be: hydrogen; hydroxyl; substituted or unsubstituted alkyl of 1 to 8 carbon atoms, such as, for example, methyl, ethyl, cyclopentyl, 4-methylpentyl, benzyl, and trifluoromethyl; substituted or unsubstituted phenyl, such as, for example, phenyl, m- chlorophenyl, and ⁇ -trifluormethylphenyl; halogen, such as, for example, chlorine, bromine, and fluorine; cyano; substituted or unsubstituted alkoxy of 1 to 8 carbon atoms, such as, for example, methoxy, ethoxy, 2-ethoxyethoxy, and benzyloxy; substituted or unsubstituted aryloxy, such as, for example, phenoxy, 51-chlorophenoxy, 3-pyridyloxy, 1-
- (Ri and R 2 ), (R 2 and R 3 ) , or (R 3 and R4) are joined to form a five-, six-, or seven-membered substituted or unsubstituted ring such as, for example, benzene, naphthalene, thiazole, benzothiazole, oxazole, benzoxazole, selenazole, benzoselenazole, thiazoline, oxazoline, quinoline, isoquinoline, pyridine, imidazole, benzimidazole, and indazoline.
- R 5 , R ⁇ , R 7 , and Re are independently any of the substituents given above for Ri, R 2 , R3, and R4.
- (R 5 and R 7 ) and/or (R ⁇ and Re) are joined to form a five-, six-, or seven-membered substituted or unsubstituted heterocyclic ring.
- Rg and Ri are each independently alkyl of 1 to 8 carbon atoms.
- (R 7 and Rg) and/or (Re and Ri) may be joined to form a five-, six-, or seven- membered substituted or unsubstituted ring or (Rg and Ri) may be joined to form a five-, six-, or seven- membered substituted or unsubstituted ring.
- any of the groups may be substituted by any of the well-known organic substituents, such as, for example: alkyl; alkoxy; halogen; cyano; sulfonyl; amino; alkyl amino; dialkylamino; etc., provided the presence of the substituent does not adversely affect the properties of the infra-red absorbing material required for the operation of the invention.
- the alkyl groups comprising any of these substituents preferably contain 1 to 8 carbon atoms.
- These compounds typically absorb in the region of 750 to 870 nm and thus are well suited for use with diode lasers.
- Ri, R2, R3' and R4 are independently hydrogen, chloro, methyl, ethyl, methoxy, ethoxy, on cyano.
- Ri, R 2 , R 3 , and R 4 each are hydrogen.
- R 5 and R 6 are each independently hydrogen, alkyl, alkoxyl, chloro, or acylamido.
- R5 and R ⁇ are each independently hydrogen or acylamido.
- a preferred acylamido group is acetamido (CH 3 CONH-) .
- R 7 and R ⁇ are each hydrogen and Rg and Ri are each independently alkyl of 1 to 6 carbon atoms.
- R 7 and Rg) or (R ⁇ and R l ) are joined to form a six-me bered substituted or unsubstituted ring.
- Representative preferred infra-red absorbing compounds are represented by structures AM-1 to AM-14.
- the infra-red absorbing materials may be prepared by conventional synthetic methods.
- the synthesis of compounds AM-7, AM-8, and AM-13 from the condensation of nitrosobanzenes with dicyanovinyl analogs of indan-1,3- dione is given in K. A. Bello, J. Chem. Soo. Perkin Trans. II , 815-818, 1987. Syntheses of infra-red absorbing materials are also given in Higasa, Japanese Patent Application 63/165378 (1988) .
- the infra-red absorbing materials may be present in the donor layer in any concentration which is effective for the intended purpose. " In general, concentrations of 0.1% to 10% of the coating weight have been found to be effective. A preferred concentration is 1% to 5% of the total coating weight.
- the colorant layer comprises a heat-transferable colorant or a mixture of heat-transferable colorants.
- a heat-transferable colorant is a colorant, such as, for example, a dye or a pigment, which is transferred from the donor element to the receptor sheet by the action of heat. On transfer it produces the desired color on the receptor sheet.
- Important criteria for the selection of a heat-transferable colorant are its thermal properties, brightness of shade, light and heat fastness, and facility of application to the support. For suitable performance, the colorant should transfer evenly, in a predetermined relationship to the heat applied, so that the intensity of color on the receptor sheet is smoothly related to the heat applied and good density gradation is attained.
- the colorant must be migrate from the donor element to the receiver sheet at the imaging energies employed, generally 0.2 to 2 J/cm 2 .
- Useful heat-transferable colorants include: (a) pigments dispersed in polymeric matrices which will soften or melt on heating, and (b) dyes, such as, for example, sublimable dyes.
- Useful sublimable dyes available rom Crompton and Knowles (Reading, PA) , include: Intratherm® Dark Brown (azo type. Disperse Brown 27), Intratherm® Pink 1335NT (anthraquinone type); Intratherm® Brilliant Red P-1314NT (anthraquinone type, Disperse Red 60) ; Intratherm® Red P-1339 (anthraquinone type. Disperse Violet 17); Intratherm® Blue P-1305NT (anthraquinone type.
- Disperse Blue 359) Disperse Blue 359) ; and Intratherm® Yellow 343NT (quinoline type. Disperse Yellow 54) .
- Representative sublimable dyes are disclosed in: Gregory, U.S. Patent 4,764,178; Hotta, U.S. Patent 4,541,830; Moore, U.S. Patent 4,698,651; Evans, U.S. Patent 4,695,287; Weaver, U.S. Patent 4,701,439; DeBoer, U.S. Patent 4,772,582; and DeBoer, U.S. Patent 4,942,141.
- the heat-transferable colorant and infra-red absorbing material are preferably dispersed in a polymeric binder.
- Typical binders include, but are not limited to: cellulose derivatives, such as, cellulose acetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate, cellulose acetate hydrogen phthalate; polyacetals, such as polyvinyl butyral; waxes having a softening or melting point of about 60°C to about 150°C; acrylate and methacrylate polymers and copolymers; polycarbonate; copolymers of styrene and acrylonitrile; polysulfones; and poly(phenylene oxide) .
- the binder may be used at a coating weight of about 0.1 to about 5 g/m 2 .
- any material which is dimensionally stable, capable of transmitting the radiation from the infra-red laser to the colorant layer, and not adversely affected by this radiation can be used as the support.
- Such materials include, but are not limited to: polyesters, such as, for example, polyethylene terephthalate; polyamides; polycarbonates; glassine paper; cellulose esters; fluoropolymers; polyethers; polyacetals; polyolefins; etc.
- a preferred support material is polyethylene terephthalate film.
- the support typically has a thickness of from about 2 to about 250 microns and may comprise a subbing layer, if desired. A preferred thickness is about 10 microns to about 50 microns.
- the colorant layer can be applied to the support as a dispersion in a suitable solvent, application from solution is preferred. Any suitable solvent may be used to coat the colorant layer.
- the colorant layer may be coated onto the support using conventional coating techniques or it may be printed thereon by a printing technique, such as, for example, gravure printing.
- the receptor sheet typically comprises a support and an image-receiving layer.
- the support is comprised of a dimensionally stable sheet material. It may be a transparent film, such as, for example, polyethylene terephthalate, polyether sulfone, a polyimide, a poly(vinyl alcohol-co-acetal) , or a cellulose ester, such as for example, cellulose acetate.
- the support may also be opaque, such as, for example, polyethylene terephthalate filled with a white pigment such as titanium dioxide, ivory paper, or synthetic paper, such as Tyvek® spunbonded polyolefin.
- the image receiving layer may comprise a coating of, for example, a polycarbonate, a polyurethane, a polyester, polyvinyl chloride, styrene/acrylonitrile copolymer, poly(caprolactone) , and mixtures thereof.
- the image receiving layer may be present in any amount which is effective for the intended purpose. In general, good results have been obtained at coating weights of 1 to 5 g/m 2 .
- the donor elements are used to form a colored image by thermal colorant transfer. This process comprises imagewise exposure of the donor element with an infra ⁇ red laser so that colorant is transferred to the receptor sheet to form a colored image.
- the donor element may be used in sheet form or in the form of a continuous roll or ribbon.
- the donor element may comprise a single color or it may comprise alternating areas of different colors, such as, for example, cyan, magenta, yellow, and black.
- diode lasers emitting in the region of 750 to 870 nm offer substantial advantage in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation.
- Diode lasers emitting in the range of 800 to 830 nm are preferred.
- Such lasers are commercially available from, for example. Spectra Diode Laboratories (San Jose, CA) .
- a transfer assemblage comprises a donor element and a receiver sheet in which the colorant layer of the donor element is contiguous to the image receiving layer of the receiver sheet.
- This assemblage may be preassembled as an integral unit when a single colored image is desired. This may be done by reversibly adhering the donor element and the receiver sheet together at their margins. After imagewise exposure, the they are separated to reveal the image on the receiver sheet.
- the assemblage When a multicolor image is to be produced, the assemblage is formed a plurality of times. After the first colored image is transferred, the assemblage is separated and a second donor element (or another area of the same donor element which comprises a differently colored heat-transferable colorant) is brought in contact with the receiver sheet and imagewise exposed in register with the first image. The process is repeated with donor elements containing differently colored heat- transferable colorants as many times as desired.
- a preferred process consists of transferring cyan, yellow, and magenta images to produce a three colored image.
- the donor element is adapted for the production of both single color and multicolor images by a laser- induced thermal transfer process. It can be used to obtain prints of images which have been recorded electronically by various electronic devices, such as color video cameras. It can also be used to generate hard copy output in various proofing applications.
- AM-7 N-(2-((1,3-bis(Dicyanomethylene)-1,3- dihydro-2H-inden-2-ylidene)amino)-5- (diethylamino)phenyl)acetamide; CAS
- AM-13 N-[6-[[1,3-bis(Dicyanomethylene)-1,3- dihydro-2H-inden-2-ylidene]amino-l- ethyl-l,2,3,4-tetrahydro-2,2,4- trimethyl-7-quinolinyl]propanamide
- coating solution refers .to the mixture of solvent and additives which is coated on the support, even though some of the additives may be in suspension rather than in solution. Amounts are expressed in parts by weight.
- Example I A coating solution containing the following ingredients, expressed in parts by weight, was made up: Red P-1339, 0.20; Lexan® 1500, 0.20; AM7, 0.016; and dichloromethane, 9.58. The composition was stirred to completely dissolve the solids and coated on an about 100 micron thick polyethylene terephthalate film with a doctor knife at about 50 micron wet gap and air dried to form the donor element.
- the coated side of the donor element was contacted with a receptor sheet of Tektronix thermal transfer paper (Tektronix Co., Wilsonville, OR) by tightly taping them together on a test drum to form a thermal transfer assemblage.
- the uncoated side of the donor element was exposed on a rotating drum with a 100 W infra-red laser emitting at 830 nm (Spectra Diode Laboratories, Inc., San Jose, CA) . At 0.38 J/cm 2 , bright magenta lines about 8 micron wide were obtained on the receptor sheet. A control with no infra-red absorbing material showed no image.
- Example 2 A coating solution containing the following ingredients, was made up: Red P-1339, 0.20; CAB, 0.20; AM7, 0.016; and dichloromethane, 9.58. The composition was dissolved, coated, and imaged as in Example 1. At 0.38 J/cm 2 , bright magenta lines about 8 micron wide were obtained on the receptor sheet.
- a coating solution containing the following ingredients was made up: Red P-1339, 0.20; Lexan® 1500, 0.20; AM8, 0.016; and dichloromethane, 9.58.
- the composition was dissolved, coated, and imaged as in Example 1. At 0.38 J/cm 2 , bright magenta lines about 8 micron lines were obtained on the receptor sheet.
- Example 4 A coating solution containing the following ingredients, was made up: Red P-1339, 0.20; CAB, 0.20; AM8, 0.016, and dichloromethane, 9.58. The composition was dissolved, coated, and imaged as in Example 1. At 0.38 J/cm 2 , bright magenta lines about 8 micron wide were obtained on the receptor sheet.
- Example 5 A coating solution containing the following ingredients, was made up: Red P-1339, 0.20; Lexan® 1500, 0.20; AM13, 0.016; and dichloromethane, 9.58. The composition was dissolved, coated, and imaged as in
- Example 1 At 0.38 J/cm 2 , bright magenta lines about 8 micron lines were obtained on the receptor sheet.
- Example 6 A coating solution containing the following ingredients, was made up: Red P-1339, 0.20; CAB, 0.20; AM13, 0.016, and dichloromethane, 9.58. The composition was dissolved, coated, and imaged as in Example 1. At 0.38 J/cm 2 , bright magenta lines about 8 micron wide were obtained on the receptor sheet.
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93900933A EP0617670A1 (en) | 1991-12-20 | 1992-12-14 | Thermal transfer imaging with infrared laser and azamethine dyes |
JP5511683A JPH07504130A (en) | 1991-12-20 | 1992-12-14 | Thermal transfer image formation using infrared laser and azamethine dye |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81119691A | 1991-12-20 | 1991-12-20 | |
US07/811,196 | 1991-12-20 |
Publications (1)
Publication Number | Publication Date |
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WO1993012939A1 true WO1993012939A1 (en) | 1993-07-08 |
Family
ID=25205847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US1992/010554 WO1993012939A1 (en) | 1991-12-20 | 1992-12-14 | Thermal transfer imaging with infrared laser and azamethine dyes |
Country Status (3)
Country | Link |
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EP (1) | EP0617670A1 (en) |
JP (1) | JPH07504130A (en) |
WO (1) | WO1993012939A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9221986B2 (en) | 2009-04-07 | 2015-12-29 | Sensient Colors Llc | Self-dispersing particles and methods for making and using the same |
CN111454177A (en) * | 2020-04-09 | 2020-07-28 | 南方科技大学 | Photo-induced non-adiabatic fading type photo-thermal material and preparation method and application thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0287377A2 (en) * | 1987-04-14 | 1988-10-19 | Sumitomo Chemical Company, Limited | Azamethine compounds, process for preparing the same and a medium for recording optical information using such compounds |
EP0375517A1 (en) * | 1988-12-19 | 1990-06-27 | Sumitomo Chemical Company, Limited | Cyan dye-donor element used in thermal transfer and thermal transfer sheet using it |
EP0383212A2 (en) * | 1989-02-15 | 1990-08-22 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transfer sheet |
EP0384040A1 (en) * | 1989-02-24 | 1990-08-29 | Agfa-Gevaert N.V. | Dye-donor element for thermal dye sublimation transfer |
EP0453020A1 (en) * | 1990-04-20 | 1991-10-23 | Agfa-Gevaert N.V. | Black colored thermal dye sublimation transfer donor element |
-
1992
- 1992-12-14 EP EP93900933A patent/EP0617670A1/en not_active Withdrawn
- 1992-12-14 JP JP5511683A patent/JPH07504130A/en active Pending
- 1992-12-14 WO PCT/US1992/010554 patent/WO1993012939A1/en not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0287377A2 (en) * | 1987-04-14 | 1988-10-19 | Sumitomo Chemical Company, Limited | Azamethine compounds, process for preparing the same and a medium for recording optical information using such compounds |
EP0375517A1 (en) * | 1988-12-19 | 1990-06-27 | Sumitomo Chemical Company, Limited | Cyan dye-donor element used in thermal transfer and thermal transfer sheet using it |
EP0383212A2 (en) * | 1989-02-15 | 1990-08-22 | Dai Nippon Insatsu Kabushiki Kaisha | Heat transfer sheet |
EP0384040A1 (en) * | 1989-02-24 | 1990-08-29 | Agfa-Gevaert N.V. | Dye-donor element for thermal dye sublimation transfer |
EP0453020A1 (en) * | 1990-04-20 | 1991-10-23 | Agfa-Gevaert N.V. | Black colored thermal dye sublimation transfer donor element |
Non-Patent Citations (3)
Title |
---|
DATABASE WPIL Week 9035, Derwent Publications Ltd., London, GB; AN 90-266091 * |
DATABASE WPIL Week 9231, Derwent Publications Ltd., London, GB; AN 92-255535 * |
PATENT ABSTRACTS OF JAPAN vol. 15, no. 249 (M-1128)25 June 1991 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9221986B2 (en) | 2009-04-07 | 2015-12-29 | Sensient Colors Llc | Self-dispersing particles and methods for making and using the same |
CN111454177A (en) * | 2020-04-09 | 2020-07-28 | 南方科技大学 | Photo-induced non-adiabatic fading type photo-thermal material and preparation method and application thereof |
CN111454177B (en) * | 2020-04-09 | 2023-04-07 | 南方科技大学 | Photo-induced non-adiabatic fading type photo-thermal material and preparation method and application thereof |
Also Published As
Publication number | Publication date |
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EP0617670A1 (en) | 1994-10-05 |
JPH07504130A (en) | 1995-05-11 |
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