CA2018037A1 - Infrared absorbing chalcogenopyryloarylidene dyes for dye-donor element used in laser-induced thermal dye transfer - Google Patents
Infrared absorbing chalcogenopyryloarylidene dyes for dye-donor element used in laser-induced thermal dye transferInfo
- Publication number
- CA2018037A1 CA2018037A1 CA002018037A CA2018037A CA2018037A1 CA 2018037 A1 CA2018037 A1 CA 2018037A1 CA 002018037 A CA002018037 A CA 002018037A CA 2018037 A CA2018037 A CA 2018037A CA 2018037 A1 CA2018037 A1 CA 2018037A1
- Authority
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- Canada
- Prior art keywords
- dye
- substituted
- independently represents
- heterocyclic ring
- infrared
- 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.)
- Abandoned
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
- B41M5/46—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—Infra-red 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/913—Material designed to be responsive to temperature, light, moisture
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Abstract
-i-INFRARED ABSORBING CHALCOGENOPYRYLO-ARYLIDENE DYES FOR DYE-DONOR ELEMENT USED
IN LASER-INDUCED THERMAL DYE TRANSFER
Abstract A dye-donor element for laser-induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein the infrared-absorbing material is a chalcogenopyrylo-arylidene dye. In a preferred embodiment, the chalcogenopyrylo-arylidene dye has the following formula:
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5--ii-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
IN LASER-INDUCED THERMAL DYE TRANSFER
Abstract A dye-donor element for laser-induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein the infrared-absorbing material is a chalcogenopyrylo-arylidene dye. In a preferred embodiment, the chalcogenopyrylo-arylidene dye has the following formula:
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5--ii-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
Description
3~
INERARED ABSORBING CHALCOGENOPYRYLO-ARYLIDENE DYES FOR DYE-~ONOR ELEMENT USED
IN LASER-INDUCED THERMAL DYE TRANSFER
This invention relates to dye-donor elements used in laser-induced thermal dye transfer, and more particularly to the use of certain infrared absorbing chalcogenopyrylo-arylidene dyes.
In recent years, thermal transfer systems have been developed to obtain prints from pictures which have been generatzd electronically from a color video camera. According to one way of obtaining suc~
prints, an electronic picture is first subjected to co~or 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. To obtain the print, 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 hea~ing 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 CQpy iS thus obtained which corresponds to the original picture viewed on a ~creen. 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 l'Apparatus and Method For Controlling A Thermal Printer Apparatus," issued November 4, 1986.
Another way to thermally obtain a print using the electronic signals described above is to use a laser instead o~ a thermal printing head. In ~ .. "
-:
~, . . . . .
INERARED ABSORBING CHALCOGENOPYRYLO-ARYLIDENE DYES FOR DYE-~ONOR ELEMENT USED
IN LASER-INDUCED THERMAL DYE TRANSFER
This invention relates to dye-donor elements used in laser-induced thermal dye transfer, and more particularly to the use of certain infrared absorbing chalcogenopyrylo-arylidene dyes.
In recent years, thermal transfer systems have been developed to obtain prints from pictures which have been generatzd electronically from a color video camera. According to one way of obtaining suc~
prints, an electronic picture is first subjected to co~or 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. To obtain the print, 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 hea~ing 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 CQpy iS thus obtained which corresponds to the original picture viewed on a ~creen. 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 l'Apparatus and Method For Controlling A Thermal Printer Apparatus," issued November 4, 1986.
Another way to thermally obtain a print using the electronic signals described above is to use a laser instead o~ a thermal printing head. In ~ .. "
-:
~, . . . . .
2~8(~37 such a system, the donor sheet includes a material which strongly absorbs at the wavelength of the laser. When the donor is irradiated, 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 ~aporization 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 ~eam 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.
In GB 2,083,726A, the absoxbing material which is disclosed for use in their laser system is carbon. There is a problem with using carbon as the absorbing material in that it is particulate and has a tendency to clump when coated ~hich 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 would be desirable to find an absorbing material which did not have these disadvanta~es.
These and other objects are achieved in accordance with this invention which relates to a dye-donor element for laser-induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein the infrared-absorbing material is a chalcogeno-pyrylo-arylidene dye~
In a preferred embodiment of the invention, the chalcogenopyrylo-arylidene dye has the following formula:
~ t~ R3 X0 Rn 10 wherein:
Rl and R2 each independently represents hydrogen, halogen such as chlorine, bromine, fluorine or iodine; cyano; alkoxy such as methoxy, 2-ethoxyethoxy or benzyloxy;
aryloxy such as phenoxy, 3 pyridyloxy, l-naphthoxy or 3-thienyloxy; acyloxy such as acetoxy, benzoyloxy or phenylacetoxy;
aryloxycarbonyl such as phenoxycarbonyl or m-methoxyphenoxycarbonyl; alkoxycarbonyl such as methoxycarbonyl, butoxycarbonyl or 2-cyanoethoxycarbonyl; sulfonyl such as methanesulfonyl, cyclohexanesulfonyl t p-toluenesulfonyl, 6-quinolinesulfonyl or 2-naphthalenesulfonyl; carbamoyl such as N-phenylcarbamoyl, N,N-dimethylcarbamoyl, N-phenyl-N-ethylcarbamoyl or N-isopropyl-carbamoyl; acyl such as benzoyl, phenylacetyl or acetyl; acylamido such aæ
p-toluenesulfonamido, benzamido or acetamido; alkylamino such as diethylamino, ethylbenzylamino or isopropylamino; :~
arylamino such as anilino, diphenylamino or N-ethylanilino; or a substituted or :-~
unsubstituted alkyl1 aryl or hetaryl group, such as cyclopentyl, t-butyl, ~-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, ~ 37 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m~tolyl;
or any of Rl and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7 membered substituted or unsubstituted carbocyclic or heterocyclic ring, such ~s tetrahydropyran, cyclopentene or 4,4~dimethylcyclohexene;
R3 and R6 each independently represents Rl or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring, thus forming a multicyclic ring system such as naphthalene, guinoline, indole or benzothiazole;
R4 and R5 each independently represents ~:
a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms such as those listed above for Rl;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring, thus ~orming a multicyclic system such as tetrahydroquinoline or julolidine;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion such as CF3S03, I, p-~CH3)C6H4S03, CF3C02, Br, Cl, PF6 or C104;
~q~ 37 n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
In a preferred embodiment of the invention, Y is sulfur. In another preferred embodiment, Rl is dimethylaminophenyl. In still another preferred embodiment, R3 is phenyl and R4 and R5 are both methyl.
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 about O.OS to about 0.5 g/m within the dye layer itself or in an adjacent layer.
The above infrared absorbing dyes may be synthesized by procedures similar those described in Helv. Chim. Acta 39, 217 (1956).
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 U.S. Patent 4,772,582. The spacer beads may be coated with a polymeric binder if desired.
Dyes included within the scope of the invention include the following:
2~1l 8(:~37 Dye l: (CH ) N6~ / \ CH-CX /~=\S
C10 ~
~max = 714 in dichloromethane Dye 2: (CX3)2N-\ /~=f CH- I ~ - C6H5 oclo4e ~ ~ ~T~
N(CH3~2 15~max = 705 in dichloromethane Dve 3 (CH3~2N~ =cH-cH=~ C6x5 20C104e C6X5 ~v Q4: (C2~5)2N--\ /o=CH-CH= \ /~
2SC104 t-C4~9 C;;/CH3 /C6H5 CH3\ ~ CH-CH=-\ /S
30 ~YQ-~ CH3 --\CH~ -O~H~ CH3 5 D~e 6: (n-C3H7)~N-CF3C02~ \CH3 C6~5 2~ ` 37 Dye 7: (C2H5 )2N~ =C--CH=~ S
=~ 1 =~
C104e I~t\ C6~5 N( C2H5 ) 2 ~8 C2H5~N~ \ C S_ /C6H5 C6H5CH2 CH3 ~ -- ~r=o\C H
Cl Dve 9: 0\ ~ =C-CH=~ o ~F3 I~ ,0 3 ,T~
I~o, Dye 10: ( cH3 ) 2r~ =CH ~ /C~3 t~S
In GB 2,083,726A, the absoxbing material which is disclosed for use in their laser system is carbon. There is a problem with using carbon as the absorbing material in that it is particulate and has a tendency to clump when coated ~hich 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 would be desirable to find an absorbing material which did not have these disadvanta~es.
These and other objects are achieved in accordance with this invention which relates to a dye-donor element for laser-induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein the infrared-absorbing material is a chalcogeno-pyrylo-arylidene dye~
In a preferred embodiment of the invention, the chalcogenopyrylo-arylidene dye has the following formula:
~ t~ R3 X0 Rn 10 wherein:
Rl and R2 each independently represents hydrogen, halogen such as chlorine, bromine, fluorine or iodine; cyano; alkoxy such as methoxy, 2-ethoxyethoxy or benzyloxy;
aryloxy such as phenoxy, 3 pyridyloxy, l-naphthoxy or 3-thienyloxy; acyloxy such as acetoxy, benzoyloxy or phenylacetoxy;
aryloxycarbonyl such as phenoxycarbonyl or m-methoxyphenoxycarbonyl; alkoxycarbonyl such as methoxycarbonyl, butoxycarbonyl or 2-cyanoethoxycarbonyl; sulfonyl such as methanesulfonyl, cyclohexanesulfonyl t p-toluenesulfonyl, 6-quinolinesulfonyl or 2-naphthalenesulfonyl; carbamoyl such as N-phenylcarbamoyl, N,N-dimethylcarbamoyl, N-phenyl-N-ethylcarbamoyl or N-isopropyl-carbamoyl; acyl such as benzoyl, phenylacetyl or acetyl; acylamido such aæ
p-toluenesulfonamido, benzamido or acetamido; alkylamino such as diethylamino, ethylbenzylamino or isopropylamino; :~
arylamino such as anilino, diphenylamino or N-ethylanilino; or a substituted or :-~
unsubstituted alkyl1 aryl or hetaryl group, such as cyclopentyl, t-butyl, ~-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, ~ 37 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m~tolyl;
or any of Rl and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7 membered substituted or unsubstituted carbocyclic or heterocyclic ring, such ~s tetrahydropyran, cyclopentene or 4,4~dimethylcyclohexene;
R3 and R6 each independently represents Rl or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring, thus forming a multicyclic ring system such as naphthalene, guinoline, indole or benzothiazole;
R4 and R5 each independently represents ~:
a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms such as those listed above for Rl;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring, thus ~orming a multicyclic system such as tetrahydroquinoline or julolidine;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion such as CF3S03, I, p-~CH3)C6H4S03, CF3C02, Br, Cl, PF6 or C104;
~q~ 37 n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
In a preferred embodiment of the invention, Y is sulfur. In another preferred embodiment, Rl is dimethylaminophenyl. In still another preferred embodiment, R3 is phenyl and R4 and R5 are both methyl.
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 about O.OS to about 0.5 g/m within the dye layer itself or in an adjacent layer.
The above infrared absorbing dyes may be synthesized by procedures similar those described in Helv. Chim. Acta 39, 217 (1956).
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 U.S. Patent 4,772,582. The spacer beads may be coated with a polymeric binder if desired.
Dyes included within the scope of the invention include the following:
2~1l 8(:~37 Dye l: (CH ) N6~ / \ CH-CX /~=\S
C10 ~
~max = 714 in dichloromethane Dye 2: (CX3)2N-\ /~=f CH- I ~ - C6H5 oclo4e ~ ~ ~T~
N(CH3~2 15~max = 705 in dichloromethane Dve 3 (CH3~2N~ =cH-cH=~ C6x5 20C104e C6X5 ~v Q4: (C2~5)2N--\ /o=CH-CH= \ /~
2SC104 t-C4~9 C;;/CH3 /C6H5 CH3\ ~ CH-CH=-\ /S
30 ~YQ-~ CH3 --\CH~ -O~H~ CH3 5 D~e 6: (n-C3H7)~N-CF3C02~ \CH3 C6~5 2~ ` 37 Dye 7: (C2H5 )2N~ =C--CH=~ S
=~ 1 =~
C104e I~t\ C6~5 N( C2H5 ) 2 ~8 C2H5~N~ \ C S_ /C6H5 C6H5CH2 CH3 ~ -- ~r=o\C H
Cl Dve 9: 0\ ~ =C-CH=~ o ~F3 I~ ,0 3 ,T~
I~o, Dye 10: ( cH3 ) 2r~ =CH ~ /C~3 t~S
3 \ _ / 3 CH3 '~
( ~3)2N~ CH--CE~-~ \5 C104e ~0 -: i .
'.
;'' : ' , ' :
2~(137 Dve 12: (CH3)2N-~ ~=C-CH=~ ~-C6H5 C104e 0\ ~ t6~5 N(CH3)2 Dye l~: (CH3)2N--o~ ~- ~CH--CH ~ t ~-C6H5 C104 C6~5 Dye 14: (C2~5)2N-~ ' `
=- =4~
C104e t-C4H9 ~, ~ \ 63 /-=~/ 3 .= /C6H5 CH3\ /N=-\ /=CH-CH~-\ ~ e 3 CH; ~ -O~H GE
6~ 3/S~ /C6H
Dye 16 (n-C3N7)2N=-~ ~ CH C
CF3C2~ C2H5 ~t ` 6 5 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. Especially good results have been obtained with sublimable dyes. Examples of sublimable dyes include anthraquinone dyes, e.g., Sumikalon Violet ~}~ 3 RSTM (Sumitomo Chemical Co., Ltd.), Dianix Fast Violet 3R-FSTM (Mitsubishi Chemical Industries, Ltd.), and Kayalon Polyol Brilliant ~lue N-~GM~M
and KST Black 146TM (Nippon Kayaku Co., Ltd.); azo dyes such as Kayalon Polyol Brilliant Blue BMTM, Kayalon Polyol Dark Blue 2BMTM, and KST Black KR (Nippon Kayaku Co., Ltd.), Sumickaron Diazo Black 5G (Sumitomo Chemical Co., Ltd.), and Miktazol Black 5GHTM (Mitsui Toatsu Chemicals, Inc.); direct dyes such as Direct Dar~ Greell BTM
(Mitsubishi Chemical Industries, Ltd.) and Direct Brown MTM and Direct Fast Black DTM (Nippon Kayaku Co. Ltd.); acid dyes such as Kayanol Milling Cyanine 5RTM (Nippon Kayaku Co. Ltd.); basic dyes such as Sumicacryl Blue 6GTM (Sumitomo Chemical Co., Ltd.), and Aizen Malachite GreenTM (Hodogaya Chemical Co., Ltd.);
~5/ N-N~ -N(C2~5)(Cx2c6H5) NHCOCX3 (magenta) CN ~H3 IN CH ~ ~ ~ \N/ \CH3 (yellow) (:~H2C~202CNH C6H5 ~, ,-, ,CONHCX3 ~ (cyan) N--\ /-N(C2~5)2 or any of the dyes disclosed in U.S. Patent 4,541,830. The above dyes may be employed singly or 2~ 37 in combination to obtain a monochrome. The dyes may ~e used at a coverage of from about 0.05 to about 1 g/m and are preferably hydrophobic.
The dye in the dye-donor element iæ
dispersed in a polymeric binder such as a cellulose derivative, e.g., cellulose acetate hydrogen phthalate, cellulose acetate, cellulose acetate propionate, cellulo~e acetate butyrate, cellulose triacetate; a polycarbonate; poly(styrene~co-acrylonitrile), a poly(sulfone) or a poly(phenyleneoxide). The binder may be used at a coverage of from about 0.1 to about 5 g/m .
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 wit:hstand the heat generated by the laser beam. Such materials include polyesters such as poly(ethylene terephthalate);
polyamides; polycarbonates; glassine paper; condenser paper; cellulose esters such as cellulose acetate;
~luorine polymers such as polyvinylidene fluoride or poly(tetrafluoroethylene co-hexa:fluoropropylene);
polyethers 6uch as polyoxymethylene; polyacetals;
polyolefins such as polystyrene, polyethylene, polypropylene or methylpentane polymers. The support generally ~as a thickness of from about 2 to about 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 a poly(ether sulfone), a 2~ 37 polyimide, a cellulose ester such as cellulose acetate, a poly(vinyl alcohol-co-acetal) or a poly(ethylene terephthalate~. The support for the dye-receiving element may also be reflective such as baryta-coated paper, polyethylene-coated paper, white polyester ~polyester with white pigment incorporated therein), an ivory paper, a condenser paper or a synthetic paper such as duPont TyvekTM.
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 ~rom about 1 to about 5 glm .
As noted above, 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 elemen~ 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 4,541,830; 4,698,651; 4,695,287; 4,701,439;
4,757,046; 4,743,582; 4,769,360; and 4,753,922.
Thus, one-, two-, three- or four-color elements (or higher numbers also) are included within the scope of the invention.
In a preferred embodiment 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. Of course, when the process is only performed for a single color, then a monochrome dye transfer image is obtained.
Several different kinds of lasers could conceivably be used to effect the thermal trans~er of dye from a donor sheet to a receiver, such as ion gas lasers like argon and krypton; metal vapor lasers such as copper, gold, and cadmium; solid state lasers such as ruby or YAG; or diode lasers such as gallium arsenide emitting in the infrared region from 750 to 870 nm. However, in practice, the diode lasers o~fer substantial advantages in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation. In practice, be~ore 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. Thus, the construction of a ~5 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 ~rom the dye-donor elements of the invention are available commercially. There can be employed, for example, Laser Model SDL-2420-H2TM from Spectrodiode Labs, or Laser Model SLD 304 V/WTM
from Sony Corp.
A thermal dye transfer assembla~e of the invention comprises 3('37 a) a dye-donor element as described above, and b) a dye-receiving element as described above, the dye-receiving element being in a superposed relationship with the dye-donor element so that the dye layer of the donor element is adjacent to and overlying the image-receiving layer of the receiving element.
The above assemblage comprlsing 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.
When a three-color image is to be obtained, 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.
The following example is provided to illustrate the invention.
Example 1 - Magenta Dye-Donor 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/m ~, the infrared absorbing dye indicated in Table 1 below (0.14 g/m2) in a cellulose aceta~e propionate binder (2.5% acetyl, 45% propionyl) (0.27 g/m2) coated from methylene chloride.
.
, 8(}37 -~ 4-A control dye-donor element was made as above containing only the magenta imaging dye.
Other control dye-donor elements were prepared as described above but containing the following control dyes:
/C6~5 C-l (CH3)2N-~ -CE=-\ _ /0 10C104~ 't~ C~H5 N(C~3)2 ~max -- 649 nm in dichloromethane C-2 (CH ) N~ / \ -C-CH /\ /C6H5 C104~ I t 6~I5 20N(CH3~2 ~max = 670 nm in dichloromethane A commercial clay-coated matte finish lithographic printing paper (80 pound Mountie-Matte from the Seneca Paper Company) was used as the dye-receiving element.
The dye-receiver was overlaid with the dye-donor placed on a drum with a circumference of 295 mm and taped with just sufficient tension to be 30 able to see the deformation of the surface of the dye-donor by reflected light. The assembly was then exposed with the drum rotating at 180 rpm to a focused 830 nm laser beam from a Spectra Diode Labs laser model SDL-2430-H2 using a 33 micrometer spot diameter and an exposure time of 37 microseconds.
The spacing between lines was 20 micrometers, giving an overlap from line to line of 39%. The total area -15~
of dye transfer to the receiver was 6 x 6 mm. The power level of the laser was appro~imately 180 milliwatts and the exposure energy, including sverlap, was 0.1 ergs per square micron.
The Status A green reflection density of each transferred dye area was read as follows:
Table Infrared Status A Green Density Dye in Donor Transferred,,to Receiver None (control) 0.0 Control C-l 0.0 Control C-~ 0.0 Dye l 0.8 Dye 2 0-5 The above results indicate that all the coatings containing an infrared absorbing dye according to the invention gave substantially more density than the controls.
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit ~5 and scope of the invention.
( ~3)2N~ CH--CE~-~ \5 C104e ~0 -: i .
'.
;'' : ' , ' :
2~(137 Dve 12: (CH3)2N-~ ~=C-CH=~ ~-C6H5 C104e 0\ ~ t6~5 N(CH3)2 Dye l~: (CH3)2N--o~ ~- ~CH--CH ~ t ~-C6H5 C104 C6~5 Dye 14: (C2~5)2N-~ ' `
=- =4~
C104e t-C4H9 ~, ~ \ 63 /-=~/ 3 .= /C6H5 CH3\ /N=-\ /=CH-CH~-\ ~ e 3 CH; ~ -O~H GE
6~ 3/S~ /C6H
Dye 16 (n-C3N7)2N=-~ ~ CH C
CF3C2~ C2H5 ~t ` 6 5 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. Especially good results have been obtained with sublimable dyes. Examples of sublimable dyes include anthraquinone dyes, e.g., Sumikalon Violet ~}~ 3 RSTM (Sumitomo Chemical Co., Ltd.), Dianix Fast Violet 3R-FSTM (Mitsubishi Chemical Industries, Ltd.), and Kayalon Polyol Brilliant ~lue N-~GM~M
and KST Black 146TM (Nippon Kayaku Co., Ltd.); azo dyes such as Kayalon Polyol Brilliant Blue BMTM, Kayalon Polyol Dark Blue 2BMTM, and KST Black KR (Nippon Kayaku Co., Ltd.), Sumickaron Diazo Black 5G (Sumitomo Chemical Co., Ltd.), and Miktazol Black 5GHTM (Mitsui Toatsu Chemicals, Inc.); direct dyes such as Direct Dar~ Greell BTM
(Mitsubishi Chemical Industries, Ltd.) and Direct Brown MTM and Direct Fast Black DTM (Nippon Kayaku Co. Ltd.); acid dyes such as Kayanol Milling Cyanine 5RTM (Nippon Kayaku Co. Ltd.); basic dyes such as Sumicacryl Blue 6GTM (Sumitomo Chemical Co., Ltd.), and Aizen Malachite GreenTM (Hodogaya Chemical Co., Ltd.);
~5/ N-N~ -N(C2~5)(Cx2c6H5) NHCOCX3 (magenta) CN ~H3 IN CH ~ ~ ~ \N/ \CH3 (yellow) (:~H2C~202CNH C6H5 ~, ,-, ,CONHCX3 ~ (cyan) N--\ /-N(C2~5)2 or any of the dyes disclosed in U.S. Patent 4,541,830. The above dyes may be employed singly or 2~ 37 in combination to obtain a monochrome. The dyes may ~e used at a coverage of from about 0.05 to about 1 g/m and are preferably hydrophobic.
The dye in the dye-donor element iæ
dispersed in a polymeric binder such as a cellulose derivative, e.g., cellulose acetate hydrogen phthalate, cellulose acetate, cellulose acetate propionate, cellulo~e acetate butyrate, cellulose triacetate; a polycarbonate; poly(styrene~co-acrylonitrile), a poly(sulfone) or a poly(phenyleneoxide). The binder may be used at a coverage of from about 0.1 to about 5 g/m .
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 wit:hstand the heat generated by the laser beam. Such materials include polyesters such as poly(ethylene terephthalate);
polyamides; polycarbonates; glassine paper; condenser paper; cellulose esters such as cellulose acetate;
~luorine polymers such as polyvinylidene fluoride or poly(tetrafluoroethylene co-hexa:fluoropropylene);
polyethers 6uch as polyoxymethylene; polyacetals;
polyolefins such as polystyrene, polyethylene, polypropylene or methylpentane polymers. The support generally ~as a thickness of from about 2 to about 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 a poly(ether sulfone), a 2~ 37 polyimide, a cellulose ester such as cellulose acetate, a poly(vinyl alcohol-co-acetal) or a poly(ethylene terephthalate~. The support for the dye-receiving element may also be reflective such as baryta-coated paper, polyethylene-coated paper, white polyester ~polyester with white pigment incorporated therein), an ivory paper, a condenser paper or a synthetic paper such as duPont TyvekTM.
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 ~rom about 1 to about 5 glm .
As noted above, 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 elemen~ 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 4,541,830; 4,698,651; 4,695,287; 4,701,439;
4,757,046; 4,743,582; 4,769,360; and 4,753,922.
Thus, one-, two-, three- or four-color elements (or higher numbers also) are included within the scope of the invention.
In a preferred embodiment 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. Of course, when the process is only performed for a single color, then a monochrome dye transfer image is obtained.
Several different kinds of lasers could conceivably be used to effect the thermal trans~er of dye from a donor sheet to a receiver, such as ion gas lasers like argon and krypton; metal vapor lasers such as copper, gold, and cadmium; solid state lasers such as ruby or YAG; or diode lasers such as gallium arsenide emitting in the infrared region from 750 to 870 nm. However, in practice, the diode lasers o~fer substantial advantages in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation. In practice, be~ore 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. Thus, the construction of a ~5 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 ~rom the dye-donor elements of the invention are available commercially. There can be employed, for example, Laser Model SDL-2420-H2TM from Spectrodiode Labs, or Laser Model SLD 304 V/WTM
from Sony Corp.
A thermal dye transfer assembla~e of the invention comprises 3('37 a) a dye-donor element as described above, and b) a dye-receiving element as described above, the dye-receiving element being in a superposed relationship with the dye-donor element so that the dye layer of the donor element is adjacent to and overlying the image-receiving layer of the receiving element.
The above assemblage comprlsing 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.
When a three-color image is to be obtained, 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.
The following example is provided to illustrate the invention.
Example 1 - Magenta Dye-Donor 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/m ~, the infrared absorbing dye indicated in Table 1 below (0.14 g/m2) in a cellulose aceta~e propionate binder (2.5% acetyl, 45% propionyl) (0.27 g/m2) coated from methylene chloride.
.
, 8(}37 -~ 4-A control dye-donor element was made as above containing only the magenta imaging dye.
Other control dye-donor elements were prepared as described above but containing the following control dyes:
/C6~5 C-l (CH3)2N-~ -CE=-\ _ /0 10C104~ 't~ C~H5 N(C~3)2 ~max -- 649 nm in dichloromethane C-2 (CH ) N~ / \ -C-CH /\ /C6H5 C104~ I t 6~I5 20N(CH3~2 ~max = 670 nm in dichloromethane A commercial clay-coated matte finish lithographic printing paper (80 pound Mountie-Matte from the Seneca Paper Company) was used as the dye-receiving element.
The dye-receiver was overlaid with the dye-donor placed on a drum with a circumference of 295 mm and taped with just sufficient tension to be 30 able to see the deformation of the surface of the dye-donor by reflected light. The assembly was then exposed with the drum rotating at 180 rpm to a focused 830 nm laser beam from a Spectra Diode Labs laser model SDL-2430-H2 using a 33 micrometer spot diameter and an exposure time of 37 microseconds.
The spacing between lines was 20 micrometers, giving an overlap from line to line of 39%. The total area -15~
of dye transfer to the receiver was 6 x 6 mm. The power level of the laser was appro~imately 180 milliwatts and the exposure energy, including sverlap, was 0.1 ergs per square micron.
The Status A green reflection density of each transferred dye area was read as follows:
Table Infrared Status A Green Density Dye in Donor Transferred,,to Receiver None (control) 0.0 Control C-l 0.0 Control C-~ 0.0 Dye l 0.8 Dye 2 0-5 The above results indicate that all the coatings containing an infrared absorbing dye according to the invention gave substantially more density than the controls.
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit ~5 and scope of the invention.
Claims (20)
1. In a dye-donor element for laser induced thermal dye transfer comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in said dye layer, the improvement wherein said infrared-absorbing material is a chalcogenopyrylo-arylidene dye.
2. The element of Claim 1 wherein said chalcogenopyrylo-arylidene dye has the following formula wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
3. The element of Claim 2 wherein Y is sulfur.
4. The element of Claim 2 wherein R1 is dimethylaminophenyl.
5. The element of Claim 2 wherein R3 is phenyl.
6. The element of Claim 2 wherein R4 and R5 are both methyl.
7. The element of Claim 2 wherein said dye layer comprises sequential repeating areas of cyan, magenta and yellow dye.
8. In a process of forming a laser-induced thermal dye transfer image comprising a) imagewise-heating by means of a laser a dye-donor element comprising a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in said dye layer, and b) transferring a dye image to a dye-receiving element to form said laser-induced thermal dye transfer image, the improvement wherein said infrared-absorbing material is a chalcogenopyrylo-arylidene dye.
9. The process of Claim 8 wherein said chalcogenopyrylo-arylidene dye has the following formula:
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms, or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R1 or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms, or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
10. The process of Claim 9 wherein Y is sulfur.
11. The process of Claim 9 wherein R1 is dimethylaminophenyl.
12. The process of Claim 9 wherein R3 is phenyl and R4 and R5 are both methyl.
13. The process of Claim 8 wherein said support is poly(ethylene terephthalate) which is coated with sequential repeating areas of cyan, magenta and yellow dye, and said process steps are sequentially performed for each color to obtain a three-color dye transfer image.
14. In a thermal dye transfer assemblage comprising:
a) a dye-donor element comprising a support having a dye layer and an infrared absorbing material which is different from the dye in said dye layer, and b) a dye-receiving element comprising a support having thereon a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said dye-donor element so that said dye layer is adjacent to said dye image-receiving layer, the improvement wherein said infrared-absorbing material is a chalcogenopyrylo-arylidene dye.
a) a dye-donor element comprising a support having a dye layer and an infrared absorbing material which is different from the dye in said dye layer, and b) a dye-receiving element comprising a support having thereon a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said dye-donor element so that said dye layer is adjacent to said dye image-receiving layer, the improvement wherein said infrared-absorbing material is a chalcogenopyrylo-arylidene dye.
15. The assemblage of Claim 14 wherein said chalcogenopyrylo-arylidene dye has the following formula:
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
wherein:
R1 and R2 each independently represents hydrogen, halogen, cyano, alkoxy, aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of R1 and R2 may be joined together or with an adjacent aromatic ring to complete a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R3 and R6 each independently represents R or the atoms necessary to complete a 5-to 7-membered fused substituted or unsubstituted carbocyclic or heterocyclic ring;
R4 and R5 each independently represents a substituted or unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an aryl or hetaryl group having from about 5 to about 10 atoms;
or R4 and R5 may be joined together or to the carbon atom of the adjacent aromatic ring at a position ortho to the position of attachment of the anilino nitrogen to form, along with the nitrogen to which they are attached, a 5- to 7-membered heterocyclic ring;
Y is oxygen, sulfur, selenium or tellurium with the methine chain being joined ortho or para to Y;
X is a monovalent anion;
n and m are 4; and p is 1-3, with the proviso that when Y is oxygen, then p is 2 or 3.
16. The assemblage of Claim 15 wherein Y is sulfur.
17. The assemblage of Claim 15 wherein R1 is dimethylaminophenyl.
18. The assemblage of Claim 15 wherein R3 is phenyl.
19. The assemblage of Claim 15 wherein R4 and R5 are both methyl.
20. The assemblage of Claim 14 wherein said support of the dye-donor element comprises poly(ethylene terephthalate) and said dye layer comprises sequential repeating areas of cyan, magenta and yellow dye.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US366,969 | 1989-06-16 | ||
| US07/366,969 US4948776A (en) | 1989-06-16 | 1989-06-16 | Infrared absorbing chalcogenopyrylo-arylidene dyes for dye-donor element used in laser-induced thermal dye transfer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2018037A1 true CA2018037A1 (en) | 1990-12-16 |
Family
ID=23445405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002018037A Abandoned CA2018037A1 (en) | 1989-06-16 | 1990-06-01 | Infrared absorbing chalcogenopyryloarylidene dyes for dye-donor element used in laser-induced thermal dye transfer |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4948776A (en) |
| EP (1) | EP0403931B1 (en) |
| JP (1) | JPH0397590A (en) |
| CA (1) | CA2018037A1 (en) |
| DE (1) | DE69004347T2 (en) |
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| US5429909A (en) | 1994-08-01 | 1995-07-04 | Eastman Kodak Company | Overcoat layer for laser ablative imaging |
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| US5674661A (en) | 1995-10-31 | 1997-10-07 | Eastman Kodak Company | Image dye for laser dye removal recording element |
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| US5747217A (en) * | 1996-04-03 | 1998-05-05 | Minnesota Mining And Manufacturing Company | Laser-induced mass transfer imaging materials and methods utilizing colorless sublimable compounds |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2083726A (en) * | 1980-09-09 | 1982-03-24 | Minnesota Mining & Mfg | Preparation of multi-colour prints by laser irradiation and materials for use therein |
-
1989
- 1989-06-16 US US07/366,969 patent/US4948776A/en not_active Expired - Lifetime
-
1990
- 1990-06-01 CA CA002018037A patent/CA2018037A1/en not_active Abandoned
- 1990-06-12 JP JP2153842A patent/JPH0397590A/en active Granted
- 1990-06-12 EP EP90111081A patent/EP0403931B1/en not_active Expired - Lifetime
- 1990-06-12 DE DE69004347T patent/DE69004347T2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4948776A (en) | 1990-08-14 |
| DE69004347T2 (en) | 1994-05-26 |
| JPH0541439B2 (en) | 1993-06-23 |
| DE69004347D1 (en) | 1993-12-09 |
| EP0403931A1 (en) | 1990-12-27 |
| JPH0397590A (en) | 1991-04-23 |
| EP0403931B1 (en) | 1993-11-03 |
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