EP0321923A2 - Colorants cyanines absorbant des rayons infra-rouges pour un élément donneur de colorant utilisé pour le transfert thermique induit par un laser - Google Patents
Colorants cyanines absorbant des rayons infra-rouges pour un élément donneur de colorant utilisé pour le transfert thermique induit par un laser Download PDFInfo
- Publication number
- EP0321923A2 EP0321923A2 EP88121298A EP88121298A EP0321923A2 EP 0321923 A2 EP0321923 A2 EP 0321923A2 EP 88121298 A EP88121298 A EP 88121298A EP 88121298 A EP88121298 A EP 88121298A EP 0321923 A2 EP0321923 A2 EP 0321923A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- dye
- substituted
- atom
- unsubstituted
- complete
- 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.)
- Granted
Links
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title claims abstract 3
- 239000000975 dye Substances 0.000 title claims description 88
- 239000011358 absorbing material Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001450 anions Chemical class 0.000 claims abstract description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical class 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- -1 poly(ethylene terephthalate) Polymers 0.000 claims description 20
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 9
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 9
- 150000001721 carbon Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001043 yellow dye Substances 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 5
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000003384 imaging method Methods 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000007651 thermal printing Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 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
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910001914 chlorine tetroxide Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- AQHOMHAZOHQBKP-UHFFFAOYSA-N dichloromethane;1,1,2-trichloroethene Chemical group ClCCl.ClC=C(Cl)Cl AQHOMHAZOHQBKP-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene 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
- 238000007639 printing Methods 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
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
- 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 dye-donor elements used in laser-induced thermal dye transfer, and more particularly to the use of certain infrared absorbing cyanine dyes.
- thermal transfer systems have been developed to obtain prints from pictures which have been generated electronically from a color video camera.
- an electronic picture is first subjected to color separation by color filters.
- the respective color-separated images are then converted into electrical signals.
- These signals are then operated on to produce cyan, magenta and yellow electrical signals.
- These signals are then transmitted to a thermal printer.
- a cyan, magenta or yellow dye-donor element is placed face-to-face with a dye-receiving element.
- the two are then inserted between a thermal printing head and a platen roller.
- a line-type thermal printing head is used to apply heat from the back of the dye-donor sheet.
- the thermal printing head has many heating elements and is heated up sequentially in response to the cyan, magenta and yellow signals. The process is then repeated for the other two colors. A color hard copy is thus obtained which corresponds to the original picture viewed on a screen. Further details of this process and an apparatus for carrying it out are contained in U.S. Patent No. 4,621,271 by Brownstein entitled “Apparatus and Method For Controlling A Thermal Printer Apparatus,” issued November 4, 1986.
- the donor sheet includes a material which strongly absorbs at the wavelength of the laser.
- this absorbing material converts light energy to thermal energy and transfers the heat to the dye in the immediate vicinity, thereby heating the dye to its vaporization temperature for transfer to the receiver.
- the absorbing material may be present in a layer beneath the dye and/or it may be admixed with the dye.
- the laser beam is modulated by electronic signals which are representative of the shape and color of the original image, so that each dye is heated to cause volatilization only in those areas in which its presence is required on the receiver to reconstruct the color of the original object. Further details of this process are found in GB 2,083,726A.
- the absorbing material which is disclosed for use in their laser system is carbon.
- carbon As the absorbing material in that it is particulate and has a tendency to clump when coated which may degrade the transferred dye image. Also, carbon may transfer to the receiver by sticking or ablation causing a mottled or desaturated color image. It is an object of this invention to find an absorbing material which does not have these disadvantages.
- a dye-donor element for laser-induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material, characterized in that the infrared-absorbing material is a cyanine dye having the following formula: wherein: R1 and R2 each independently represents a substituted or unsubstituted alkyl group such as, CH3,- C2H5 -(CH2)2-OCH3, -(CH2)3CO2CH3, -C3H7, -C4H9, or -(CH2)3Cl; R3, R4, and R5 each independently represents hydrogen or a substituted or unsubstituted alkyl group, such as those mentioned above for R1 and R2; or R3 and R4 may be joined together, directly or through one or more methyne or methylene groups to complete a substituted or unsubstituted cyclic ring of 5 to 9 members, such as Z1 and Z2 each independently
- both R1 and R2 are methyl and J is halogen.
- R3 and R4 are joined together to complete a 6-membered cyclic ring.
- Z1 and Z2 both represent the atoms necessary to complete a benzene ring substituted with a nitro, halo or cyano group.
- both Y1 and Y2 represent a dialkyl-substituted carbon atom.
- the above infrared absorbing dyes may employed in any concentration which is effective for the intended purpose. In general, good results have been obtained at a concentration from 0.04 to 0.5 g/m2 within the dye layer itself or in an adjacent layer.
- Spacer beads may be employed in a separate layer over the dye layer in order to separate the dye-donor from the dye-receiver thereby increasing the uniformity and density of dye transfer. That invention is more fully described in DeBoer Application Serial No. 136,073 entitled "Spacer Bead Layer For Dye-Donor Element Used In Laser-Induced Thermal Dye Transfer", filed December 21, 1987.
- the spacer beads may be coated with a polymeric binder if desired.
- Dyes included within the scope of the invention include the following:
- any dye can be used in the dye layer of the dye-donor element of the invention provided it is transferable to the dye-receiving layer by the action of heat.
- sublimable dyes such as or any of the dyes disclosed in U.S. Patent 4,54l,830.
- the above dyes may be employed singly or in combination to obtain a monochrome.
- the dyes may be used at a coverage of from 0.05 to l g/m2 and are preferably hydrophobic.
- the dye in the dye-donor element is dispersed in a polymeric binder such as a cellulose derivative, e.g., cellulose acetate hydrogen phthalate, cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, cellulose triacetate; a polycarbonate; poly(styrene-co-acrylonitrile), a poly(sulfone) or a poly(phenylene oxide).
- the binder may be used at a coverage of from 0.1 to 5 g/m2.
- the dye layer of the dye-donor element may be coated on the support or printed thereon by a printing technique such as a gravure process.
- any material can be used as the support for the dye-donor element of the invention provided it is dimensionally stable and can withstand the heat generated by the laser beam.
- Such materials include polyesters such as poly(ethylene terephthalate); polyamides; polycarbonates; glassine paper; condenser paper; cellulose esters; fluorine polymers; polyethers; polyacetals; or polyolefins.
- the support generally has a thickness of from 2 to 250 ⁇ m. It may also be coated with a subbing layer, if desired.
- the dye-receiving element that is used with the dye-donor element of the invention usually comprises a support having thereon a dye image-receiving layer.
- the support may be a transparent film such as poly(ethylene terephthalate) or may also be reflective such as white polyester (polyester with white pigment incorporated therein)
- the dye image-receiving layer may comprise, for example, a polycarbonate, a polyurethane, a polyester, polyvinyl chloride, poly(styrene- co -acrylonitrile), poly(caprolactone) or mixtures thereof.
- the dye image-receiving layer may be present in any amount which is effective for the intended purpose. In general, good results have been obtained at a concentration of from l to 5 g/m2.
- the dye-donor elements of the invention are used to form a dye transfer image.
- Such a process comprises imagewise-heating a dye-donor element as described above using a laser, and transferring a dye image to a dye-receiving element to form the dye transfer image.
- the dye-donor element of the invention may be used in sheet form or in a continuous roll or ribbon. If a continuous roll or ribbon is employed, it may have only one dye or may have alternating areas of other different dyes, such as sublimable cyan and/or magenta and/or yellow and/or black or other dyes. Such dyes are disclosed in U. S. Patents 4,54l,830; 4,698,651; 4,695,287; and 4,701,439. Thus, one-, two-, three- or four-color elements (or higher numbers also) are included within the scope of the invention.
- the dye-donor element comprises a poly(ethylene terephthalate) support coated with sequential repeating areas of cyan, magenta and yellow dye, and the above process steps are sequentially performed for each color to obtain a three-color dye transfer image.
- a monochrome dye transfer image is obtained.
- ion gas lasers like argon and krypton
- metal vapor lasers such as copper, gold, and cadmium
- solid state lasers such as ruby or YAG
- diode lasers such as gallium arsenide emitting in the infrared region from 750 to 870 nm.
- the diode lasers offer substantial advantages in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation.
- any laser before any laser can be used to heat a dye-donor element, the laser radiation must be absorbed into the dye layer and converted to heat by a molecular process known as internal conversion.
- the construction of a useful dye layer will depend not only on the hue, sublimability and intensity of the image dye, but also on the ability of the dye layer to absorb the radiation and convert it to heat.
- Lasers which can be used to transfer dye from the dye-donor elements of the invention are available commercially. There can be employed, for example, Laser Model SDL-2420-H2® from Spectrodiode Labs, or Laser Model SLD 304 V/W® from Sony Corp.
- a thermal dye transfer assemblage using the invention comprises
- the above assemblage comprising these two elements may be preassembled as an integral unit when a monochrome image is to be obtained. This may be done by temporarily adhering the two elements together at their margins. After transfer, the dye-receiving element is then peeled apart to reveal the dye transfer image.
- the above assemblage is formed on three occasions during the time when heat is applied using the laser beam. After the first dye is transferred, the elements are peeled apart. A second dye-donor element (or another area of the donor element with a different dye area) is then brought in register with the dye-receiving element and the process repeated. The third color is obtained in the same manner.
- a dye-donor element according to the invention was prepared by coating an unsubbed 100 ⁇ m thick poly(ethylene terephthalate) support with a layer of the magenta dye illustrated above (0.38 g/m2), infrared absorbing dye Compound 1 (0.14 g/m2) in a cellulose acetate propionate binder (2.5% acetyl, 45% propionyl) (0.27 g/m2) coated from a cyclohexanone and butanone solvent mixture.
- a control dye-donor element was made as above but omitting the magenta imaging dye.
- a second control dye-donor element was prepared as described above on a 75 ⁇ m thick poly(ethylene terephthalate) support subbed with gelatin, but containing 0.32 g/m2 of the following control dye (a non-infrared absorbing cyanine dye).
- a third control dye-donor element was prepared similar to the second control element, but the concentration of the magenta dye was increased to 0.45 g/m2, the infrared absorbing dye was replaced with dispersed carbon (0.60 g/m2), and the cellulose acetate propionate binder (0.50 g/m2) was coated from a toluene and tetrahydrofuran solvent mixture.
- a dye-receiving element was prepared by coating a solution of Makrolon 5705® a bisphenol A-polycarbonate resin supplied by Bayer AG (4.0 g/m2) in a methylene chloride-trichloroethylene solvent mixture on a 175 ⁇ m poly(ethyleneterephthalate) support containing titanium dioxide.
- the dye-receiver was overlaid with the dye-donor placed on a drum and taped with just sufficient tension to be able to see the deformation of the surface beads.
- the assembly was then exposed on a 180 rpm rotating drum to a focused 830 nm laser beam from a Spectrodiode Labs Laser Model SDL-2420-H2® using a 50 ⁇ m spot diameter and an exposure time of 5 millisec. to transfer the areas of dye to the receiver.
- the power level was 86 milliwatts and the exposure energy was 44 microwatts/square micron.
- the dye-donor element containing Compound 1 produced a defined magenta image in the receiver with no visible color contamination from the cyanine dye.
- the Status A green reflection density was 2.3.
- the first control dye-donor element containing only the cyanine dye but no magenta image dye did not have any visible image in the receiver.
- the second control dye-donor element also did not have any visible image, which was probably due to the fact that this dye does not absorb appreciably at 830 nm, having a ⁇ -max of 600 nm.
- the third control dye-donor element containing carbon as the absorbing material produced an image but the Status A reflection density was only 1.2.
- the image had a mottled appearance probably due to the clumping of the carbon dispersion during the drying process. Small specks of carbon were also observed to transfer to the receiver.
- a dye-donor element according to the invention was prepared by coating an unsubbed 100 ⁇ m thick poly(ethylene terephthalate) support with a layer of the cyan dye illustrated above (0.40 g/m2), infrared absorbing dye Compound 2 (0.14 g/m2) in a cellulose acetate propionate binder (2.5% acetyl, 45% propionyl) (0.20 g/m2) coated from a cyclohexanone and butanone solvent mixture.
- a control dye-donor element was made as above but omitted the infrared absorbing dye.
- a dye-receiving element was prepared and processed as in Example 1.
- the dye-donor element containing Compound 2 produced a uniform cyan image in the receiver having a density of 0.7.
- the control dye-donor element did not have any visible image in the receiver.
- Dye-donors according to the invention were prepared by coating on an unsubbed 100 ⁇ m thick polyethylene terephthalate support a layer of the cyan dye illustrated above (0.38 g/m2), infrared absorbing dye Compounds 1, 3, 5 and 10 (0.13 g/m2), and CIBA-Geigy Tinuvin 770® hindered amine stabilizer (0.26 g/m2) in a cellulose nitrate binder (0.89 g/m2) coated from a dimethylformamide and butanone solvent mixture.
- a control donor coating was made as above but omitted the cyanine infrared absorbing dye.
- a dye-receiver was prepared and processed as in Example 1 except that the drum rotation was 120 rpm.
- the Status A red reflection density of the receivers were read. As shown in Table 1, except for the control which had a density of 0.2, dye-donors with added cyanine dye produced densities of 0.5 or more.
- the Status A red transmission density of the dye-donors were first read. The evaluation was done as above but no dye receiver was used; instead an air stream was blown over the donor surface to remove sublimed dye. The Status A red density of the original dye donor was compared to the residual density after the cyan image dye was sublimed away by the laser. All the densities were reduced to 1.0 or below where the cyanine dye of the invention was present, thus showing their effectiveness in positive imaging.
- Dye-donors were prepared as in Example 3 but used the magenta dye illustrated above (0.38 g/m2), omitted the stabilizer and used compounds 9, 11 and 12.
- a control donor coating was made as above, but omitted the cyanine infrared absorbing dye.
- a dye receiver was prepared and processed as in Example 1 and the receiver was read to Status A green reflection density as follows: Table 2 Infrared Dye in Donor Status A Green Density Transferred to Receiver None (control) 0.0 Compound 9 0.1 Compound 11 0.6 Compound 12 0.4
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13607487A | 1987-12-21 | 1987-12-21 | |
US136074 | 1987-12-21 | ||
US22116388A | 1988-07-19 | 1988-07-19 | |
US221163 | 1994-03-31 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0321923A2 true EP0321923A2 (fr) | 1989-06-28 |
EP0321923A3 EP0321923A3 (en) | 1990-04-25 |
EP0321923B1 EP0321923B1 (fr) | 1992-07-15 |
Family
ID=26833964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19880121298 Expired EP0321923B1 (fr) | 1987-12-21 | 1988-12-20 | Colorants cyanines absorbant des rayons infra-rouges pour un élément donneur de colorant utilisé pour le transfert thermique induit par un laser |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0321923B1 (fr) |
JP (1) | JPH022074A (fr) |
DE (1) | DE3872854T2 (fr) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0600209A1 (fr) * | 1992-11-24 | 1994-06-08 | Eastman Kodak Company | Absorbant infrarouge pour le transfer thermique de colorant induit par laser |
EP0603490A1 (fr) * | 1992-11-24 | 1994-06-29 | Eastman Kodak Company | Liant pour élément donneur de colorant pour le transfer thermique de colorant |
EP0636490A1 (fr) * | 1993-07-30 | 1995-02-01 | Eastman Kodak Company | Couche barrière pour un procédé de formation d'images par ablation au laser |
EP0685333A2 (fr) | 1992-06-05 | 1995-12-06 | Agfa-Gevaert N.V. | Matériau d'enregistrement thermosensible et procédé pour la production de plaques lithographiques à sec |
EP0771672A3 (fr) * | 1995-10-31 | 1998-01-07 | Eastman Kodak Company | Elément d'enregistrement par laser |
US5976698A (en) * | 1996-06-27 | 1999-11-02 | 3M Innovative Properties Company | Process and materials for imagewise placement of uniform spacers in flat panel displays |
EP1342585A1 (fr) | 1999-01-15 | 2003-09-10 | 3M Innovative Properties Company | Méthode de fabrication d'un dispositif électroluminescent |
US6783915B2 (en) | 1999-05-14 | 2004-08-31 | 3M Innovative Properties Company | Thermal transfer of a black matrix containing carbon black |
US7223515B1 (en) | 2006-05-30 | 2007-05-29 | 3M Innovative Properties Company | Thermal mass transfer substrate films, donor elements, and methods of making and using same |
US7670450B2 (en) | 2006-07-31 | 2010-03-02 | 3M Innovative Properties Company | Patterning and treatment methods for organic light emitting diode devices |
US7927454B2 (en) | 2007-07-17 | 2011-04-19 | Samsung Mobile Display Co., Ltd. | Method of patterning a substrate |
WO2015016678A1 (fr) | 2013-08-01 | 2015-02-05 | 주식회사 엘지화학 | Procédé de fabrication de motif métallique de structure en trois dimensions |
CN116082854A (zh) * | 2022-11-21 | 2023-05-09 | 大连理工大学 | 一类偏位取代的五甲川花菁染料及其合成方法与应用 |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5034303A (en) * | 1989-06-16 | 1991-07-23 | Eastman Kodak Company | Infrared absorbing trinuclear cyanine dyes for dye-donor element used in laser-induced thermal dye transfer |
US5126760A (en) * | 1990-04-25 | 1992-06-30 | Eastman Kodak Company | Direct digital halftone color proofing involving diode laser imaging |
DE69317458T2 (de) * | 1992-04-14 | 1998-07-09 | Konishiroku Photo Ind | Wärmeempfindliches Übertragungsaufzeichnungsmaterial |
GB9318805D0 (en) * | 1993-09-10 | 1993-10-27 | Ici Plc | Laser dye thermal fransfer printing |
KR970002416Y1 (ko) * | 1994-03-17 | 1997-03-24 | 서춘식 | 간이 차고용 골조의 체결장치 |
JP3789565B2 (ja) * | 1996-07-25 | 2006-06-28 | 富士写真フイルム株式会社 | 湿し水不要平版印刷版の形成方法 |
US20020064728A1 (en) | 1996-09-05 | 2002-05-30 | Weed Gregory C. | Near IR sensitive photoimageable/photopolymerizable compositions, media, and associated processes |
US5858583A (en) * | 1997-07-03 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Thermally imageable monochrome digital proofing product with high contrast and fast photospeed |
US5955224A (en) * | 1997-07-03 | 1999-09-21 | E. I. Du Pont De Nemours And Company | Thermally imageable monochrome digital proofing product with improved near IR-absorbing dye(s) |
US6251571B1 (en) | 1998-03-10 | 2001-06-26 | E. I. Du Pont De Nemours And Company | Non-photosensitive, thermally imageable element having improved room light stability |
DE60035078T2 (de) | 1999-01-15 | 2008-01-31 | 3M Innovative Properties Co., St. Paul | Herstellungsverfahren eines Donorelements für Übertragung durch Wärme |
US6228543B1 (en) | 1999-09-09 | 2001-05-08 | 3M Innovative Properties Company | Thermal transfer with a plasticizer-containing transfer layer |
US6521324B1 (en) | 1999-11-30 | 2003-02-18 | 3M Innovative Properties Company | Thermal transfer of microstructured layers |
US6623908B2 (en) * | 2001-03-28 | 2003-09-23 | Eastman Kodak Company | Thermal imaging composition and imaging member containing polymethine IR dye and methods of imaging and printing |
US6749993B2 (en) | 2002-02-06 | 2004-06-15 | Konica Corporation | Planographic printing precursor and printing method employing the same |
JP2006056184A (ja) | 2004-08-23 | 2006-03-02 | Konica Minolta Medical & Graphic Inc | 印刷版材料および印刷版 |
JPWO2007052470A1 (ja) | 2005-11-01 | 2009-04-30 | コニカミノルタエムジー株式会社 | 平版印刷版材料、平版印刷版、平版印刷版の作製方法及び平版印刷版の印刷方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6127291A (ja) * | 1984-07-18 | 1986-02-06 | Sony Corp | レ−ザ記録媒体及びその製造方法 |
EP0178832A2 (fr) * | 1984-10-16 | 1986-04-23 | Imperial Chemical Industries Plc | Impression par transfert thermique |
JPS62167089A (ja) * | 1986-01-20 | 1987-07-23 | Sony Corp | レ−ザ記録媒体 |
JPS62280263A (ja) * | 1986-05-29 | 1987-12-05 | Ricoh Co Ltd | シアニン色素 |
JPS6313791A (ja) * | 1986-07-04 | 1988-01-21 | Sony Corp | 光記録媒体 |
GB2193659A (en) * | 1986-07-28 | 1988-02-17 | Ricoh Kk | Optical information recording medium |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60110497A (ja) * | 1983-11-22 | 1985-06-15 | Mitsui Toatsu Chem Inc | 画像形成材料 |
JPS60180888A (ja) * | 1984-02-29 | 1985-09-14 | Ricoh Co Ltd | 感熱記録用圧力転写シ−ト |
JPS60225796A (ja) * | 1984-04-25 | 1985-11-11 | Ricoh Co Ltd | レ−ザ−用記録材料 |
JPS6270089A (ja) * | 1985-09-24 | 1987-03-31 | Ricoh Co Ltd | 感熱転写媒体 |
JPS62232461A (ja) * | 1986-04-01 | 1987-10-12 | Ricoh Co Ltd | シアニン色素 |
-
1988
- 1988-12-20 DE DE19883872854 patent/DE3872854T2/de not_active Expired - Fee Related
- 1988-12-20 EP EP19880121298 patent/EP0321923B1/fr not_active Expired
- 1988-12-21 JP JP63323179A patent/JPH022074A/ja active Granted
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6127291A (ja) * | 1984-07-18 | 1986-02-06 | Sony Corp | レ−ザ記録媒体及びその製造方法 |
EP0178832A2 (fr) * | 1984-10-16 | 1986-04-23 | Imperial Chemical Industries Plc | Impression par transfert thermique |
JPS62167089A (ja) * | 1986-01-20 | 1987-07-23 | Sony Corp | レ−ザ記録媒体 |
JPS62280263A (ja) * | 1986-05-29 | 1987-12-05 | Ricoh Co Ltd | シアニン色素 |
JPS6313791A (ja) * | 1986-07-04 | 1988-01-21 | Sony Corp | 光記録媒体 |
GB2193659A (en) * | 1986-07-28 | 1988-02-17 | Ricoh Kk | Optical information recording medium |
Non-Patent Citations (4)
Title |
---|
PATENT ABSTRACTS OF JAPAN, vol. 10, no. 176 (M-491)[2232], 20th June 1986; & JP-A-61 27 291 (SONY CORP.) 06-02-1986 * |
PATENT ABSTRACTS OF JAPAN, vol. 12, no. 1 (M-656)[2848], 6th January 1988; & JP-A-62 167 089 (SONY CORP.) 23-07-1987 * |
PATENT ABSTRACTS OF JAPAN, vol. 12, no. 172 (C-497)[3019], 21st May 1988; & JP-A-62 280 263 (RICOH CO.) 05-12-1987 * |
PATENT ABSTRACTS OF JAPAN, vol. 12, no. 212 (M-710)[3059], 17th June 1988; & JP-A-63 13 791 (SONY CORP.) 21-01-1988 * |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0685333A2 (fr) | 1992-06-05 | 1995-12-06 | Agfa-Gevaert N.V. | Matériau d'enregistrement thermosensible et procédé pour la production de plaques lithographiques à sec |
EP0600209A1 (fr) * | 1992-11-24 | 1994-06-08 | Eastman Kodak Company | Absorbant infrarouge pour le transfer thermique de colorant induit par laser |
EP0603490A1 (fr) * | 1992-11-24 | 1994-06-29 | Eastman Kodak Company | Liant pour élément donneur de colorant pour le transfer thermique de colorant |
EP0636490A1 (fr) * | 1993-07-30 | 1995-02-01 | Eastman Kodak Company | Couche barrière pour un procédé de formation d'images par ablation au laser |
EP0771672A3 (fr) * | 1995-10-31 | 1998-01-07 | Eastman Kodak Company | Elément d'enregistrement par laser |
US5976698A (en) * | 1996-06-27 | 1999-11-02 | 3M Innovative Properties Company | Process and materials for imagewise placement of uniform spacers in flat panel displays |
EP1342585A1 (fr) | 1999-01-15 | 2003-09-10 | 3M Innovative Properties Company | Méthode de fabrication d'un dispositif électroluminescent |
US6783915B2 (en) | 1999-05-14 | 2004-08-31 | 3M Innovative Properties Company | Thermal transfer of a black matrix containing carbon black |
US7223515B1 (en) | 2006-05-30 | 2007-05-29 | 3M Innovative Properties Company | Thermal mass transfer substrate films, donor elements, and methods of making and using same |
US7396632B2 (en) | 2006-05-30 | 2008-07-08 | 3M Innovative Properties Company | Thermal mass transfer substrate films, donor elements, and methods of making and using same |
US7670450B2 (en) | 2006-07-31 | 2010-03-02 | 3M Innovative Properties Company | Patterning and treatment methods for organic light emitting diode devices |
US7927454B2 (en) | 2007-07-17 | 2011-04-19 | Samsung Mobile Display Co., Ltd. | Method of patterning a substrate |
WO2015016678A1 (fr) | 2013-08-01 | 2015-02-05 | 주식회사 엘지화학 | Procédé de fabrication de motif métallique de structure en trois dimensions |
CN116082854A (zh) * | 2022-11-21 | 2023-05-09 | 大连理工大学 | 一类偏位取代的五甲川花菁染料及其合成方法与应用 |
Also Published As
Publication number | Publication date |
---|---|
DE3872854D1 (de) | 1992-08-20 |
JPH022074A (ja) | 1990-01-08 |
JPH0517037B2 (fr) | 1993-03-08 |
DE3872854T2 (de) | 1993-03-04 |
EP0321923A3 (en) | 1990-04-25 |
EP0321923B1 (fr) | 1992-07-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0321923B1 (fr) | Colorants cyanines absorbant des rayons infra-rouges pour un élément donneur de colorant utilisé pour le transfert thermique induit par un laser | |
EP0405296B1 (fr) | Colorants oxyindolizines, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0403931B1 (fr) | Colorants chalcogénopyryloarylidène, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
US4973572A (en) | Infrared absorbing cyanine dyes for dye-donor element used in laser-induced thermal dye transfer | |
EP0403930B1 (fr) | Colorants squarylium, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0321922B1 (fr) | Couche d'espacement à base de perles pour un élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0408907B1 (fr) | Colorants de type quinoide, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
US4950639A (en) | Infrared absorbing bis(aminoaryl)polymethine dyes for dye-donor element used in laser-induced thermal dye transfer | |
US4950640A (en) | Infrared absorbing merocyanine dyes for dye-donor element used in laser-induced thermal dye transfer | |
US4948777A (en) | Infrared absorbing bis(chalcogenopyrylo)polymethine dyes for dye-donor element used in laser-induced thermal dye transfer | |
EP0408908B1 (fr) | Colorants de type complexe nickel-dithiolène, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0373571B1 (fr) | Elément récepteur de colorant contenant des perles d'espacement pour le transfert thermique de colorant induit par laser | |
US4912083A (en) | Infrared absorbing ferrous complexes for dye-donor element used in laser-induced thermal dye transfer | |
EP0403933B1 (fr) | Colorants cyanines trinucléaires, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0403934B1 (fr) | Colorants de type oxonol, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser | |
EP0407744B1 (fr) | Colorants polyméthiniques pontés par un indène, absorbant l'infrarouge pour élément donneur de colorant utilisé dans le transfert thermique de colorant induit par laser |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A2 Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Kind code of ref document: A3 Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE |
|
17P | Request for examination filed |
Effective date: 19900406 |
|
17Q | First examination report despatched |
Effective date: 19911111 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
RBV | Designated contracting states (corrected) |
Designated state(s): BE CH DE FR GB IT LI NL |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): BE CH DE FR GB IT LI NL |
|
REF | Corresponds to: |
Ref document number: 3872854 Country of ref document: DE Date of ref document: 19920820 |
|
ET | Fr: translation filed | ||
ITF | It: translation for a ep patent filed | ||
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
26N | No opposition filed | ||
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19941209 Year of fee payment: 7 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19941214 Year of fee payment: 7 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 19941229 Year of fee payment: 7 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19941231 Year of fee payment: 7 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Effective date: 19951231 Ref country code: LI Effective date: 19951231 Ref country code: CH Effective date: 19951231 |
|
BERE | Be: lapsed |
Owner name: EASTMAN KODAK CY (A NEW JERSEY CORP.) Effective date: 19951231 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19960701 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Effective date: 19960830 |
|
NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 19960701 |
|
REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20051104 Year of fee payment: 18 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED. Effective date: 20051220 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20051230 Year of fee payment: 18 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20070703 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20061220 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20061220 |