CA2018042A1 - Infrared absorbing squarylium dyes for dye-donor element used in laser-induced thermal dye transfer - Google Patents
Infrared absorbing squarylium dyes for dye-donor element used in laser-induced thermal dye transferInfo
- Publication number
- CA2018042A1 CA2018042A1 CA002018042A CA2018042A CA2018042A1 CA 2018042 A1 CA2018042 A1 CA 2018042A1 CA 002018042 A CA002018042 A CA 002018042A CA 2018042 A CA2018042 A CA 2018042A CA 2018042 A1 CA2018042 A1 CA 2018042A1
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- Prior art keywords
- dye
- joined together
- substituted
- heterocyclic ring
- layer
- 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
- Y10S430/145—Infrared
-
- 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 SQUARYLIUM
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 squarylium dye which is located in the dye layer.
In a preferred embodiment, the squarylium dye has the following formula:
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
-ii-R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
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 squarylium dye which is located in the dye layer.
In a preferred embodiment, the squarylium dye has the following formula:
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
-ii-R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
Description
2`~
IMFRARED ABSORBING SQUARYLIUM
DYES FOR DYE-DONOR 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 o~ certain infrared absorbing squarylium dyes.
In recent years, thermal transfer systems have been developed to obtain prints from pictures which have been generated electronically from a color video camera. According to one way of obtaining such prints, an electronic picture is first subjected to color separation by color filters. The respective color-separated images are then converted into electrical signals. The3e signals are then operated on to produce cyan, magenta and yellow electrical ~ignals. 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 i9 used to apply heat ~rom the back of the dye-donor sheet. The thermal printing head has many heating elements and is heated up sequerltially in re~ponse to the cyan, magenta and yellow signalg. 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
IMFRARED ABSORBING SQUARYLIUM
DYES FOR DYE-DONOR 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 o~ certain infrared absorbing squarylium dyes.
In recent years, thermal transfer systems have been developed to obtain prints from pictures which have been generated electronically from a color video camera. According to one way of obtaining such prints, an electronic picture is first subjected to color separation by color filters. The respective color-separated images are then converted into electrical signals. The3e signals are then operated on to produce cyan, magenta and yellow electrical ~ignals. 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 i9 used to apply heat ~rom the back of the dye-donor sheet. The thermal printing head has many heating elements and is heated up sequerltially in re~ponse to the cyan, magenta and yellow signalg. 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
3~ of this process and an apparatus for carrying it out are contained in U.S. Patent No. 4,6~ 71 by Brownstein entitled "Apparatus and Method For Controlling A Therma~ Printer Apparatus," is~ued November 4, 1986.
Another way to thermally obtain a print using the electronic signals described abo~e is to use a laser instead of a thermal printing head. In 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 ener~y to thermal energy and transfers the heat to the dye in the immediate vicinity, thereby heating ~he 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.
Japanese Kokai 63/319,191 relates to a transfer material fox heat-sensitive recording comprising a layer containing a substance which generates heat upon irradiation by a laser beam and another layer containing a subliming dye on a support. Compound~ 14 and 15 of this reference which generate heat upon irradiation are similar to the squarylium dyes described herein. However, the materials in the reference are specifically described as being located in a separate layer from the dye layer, rather than being in the dye layer itself.
There is a problem with havin~ the infrared-absorbing materials located in a separate layer in that the transfer efficiency, i.e., the density per unit of laser input energy, is not as great as it would be if the infrared-absorbing material were located in the dye layer.
Accordingly, this invention relates to a dye-donor element for laser-induced thermal dye transfer comprisin~ a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein 2~ 2 the infrared-absorbing material is a squarylium dye which is loca~ed in the dye layer.
In a preferred embodiment of the in~ention, the squarylium dye has the following formula:
RlR2 Oe R3R4 S/~tC=c~ ~C C m~N~8 wherein:
Rl, R2, R3 and R4 each independently represents hydrogen; hydroxy; 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 phenoxyearbonyl or m-methoxy-phenoxycarbonyl; alkoxycarbonyl such as methoxycarbonyl, butoxycarbonyl or 2-cyanoethoxycarbonyl; sulfonyl such as methanesul~onyl or cyclohexanesulfonyl, p-toluenesulfonyl, 6-quinolinesulfonyl or 2-naphthaIenesulfonyl; carbamoyl such as N-phenylcarbamoyl, N,N-dimethylcarbamoyl, N-phenyl-N-ethylcarbamoyl or N isopropylcarbamoyl; acyl ~uch as benzoyl, phenylacetyl or acetyl; acylamido such as 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 alkyl, aryl or he~aryl group, " ~
': '
Another way to thermally obtain a print using the electronic signals described abo~e is to use a laser instead of a thermal printing head. In 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 ener~y to thermal energy and transfers the heat to the dye in the immediate vicinity, thereby heating ~he 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.
Japanese Kokai 63/319,191 relates to a transfer material fox heat-sensitive recording comprising a layer containing a substance which generates heat upon irradiation by a laser beam and another layer containing a subliming dye on a support. Compound~ 14 and 15 of this reference which generate heat upon irradiation are similar to the squarylium dyes described herein. However, the materials in the reference are specifically described as being located in a separate layer from the dye layer, rather than being in the dye layer itself.
There is a problem with havin~ the infrared-absorbing materials located in a separate layer in that the transfer efficiency, i.e., the density per unit of laser input energy, is not as great as it would be if the infrared-absorbing material were located in the dye layer.
Accordingly, this invention relates to a dye-donor element for laser-induced thermal dye transfer comprisin~ a support having thereon a dye layer and an infrared-absorbing material which is different from the dye in the dye layer, and wherein 2~ 2 the infrared-absorbing material is a squarylium dye which is loca~ed in the dye layer.
In a preferred embodiment of the in~ention, the squarylium dye has the following formula:
RlR2 Oe R3R4 S/~tC=c~ ~C C m~N~8 wherein:
Rl, R2, R3 and R4 each independently represents hydrogen; hydroxy; 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 phenoxyearbonyl or m-methoxy-phenoxycarbonyl; alkoxycarbonyl such as methoxycarbonyl, butoxycarbonyl or 2-cyanoethoxycarbonyl; sulfonyl such as methanesul~onyl or cyclohexanesulfonyl, p-toluenesulfonyl, 6-quinolinesulfonyl or 2-naphthaIenesulfonyl; carbamoyl such as N-phenylcarbamoyl, N,N-dimethylcarbamoyl, N-phenyl-N-ethylcarbamoyl or N isopropylcarbamoyl; acyl ~uch as benzoyl, phenylacetyl or acetyl; acylamido such as 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 alkyl, aryl or he~aryl group, " ~
': '
-4- :
such as cyclopentyl, t-butyl, 2-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m-tolyl;
or any of said Rl, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted car~ocyclic or heterocyclic ring, such as benzene, naphthalene, indole, indazoline or tetrahydroquinoline;
R5, R6! R7 and R8 each independently represents hydrogen, a substituted or .
unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an axyl or hetaryl group having from about 5 to :~
about 10 atoms such as cyclopentyl, t-kutyl, 2-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m-tolyl;
or R5 and R6 or R7 and R~ may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring such as morpholine, pyrrolidine or piperidine; and n and m are each independently 1 to 4.
In a preferred embodiment of the invention, R5, R6, R7 and R8 are each ethyl. In another preferred embodiment, R5 and R6 are joined ~ogether to form a 5- to 7-membered nitrogen~containing heterocyclic ring and R7 and R8 are jolned together to form a 5- to 7-membered nitrogen-containing heterocyclic ring. In still another preferred embodiment, Rl and R2 are joined to~ether to form a benzene ring. In another pre~erred embodiment, Rl and R5 are joined together to form an indole ring and R4 and R7 are : joined together to form an indolium ring.
~ ~ ~b~ ~
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 0.05 to about 0,5 g/m2 within the dye layer.
The above infrared absorbing dyes m~y be synthesized by procedures similar those described in Dyes & Pigment , 9, 85-107 (1988).
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 deæired.
Dyes included within the scope of the invention include the following:
. ' ~
:
Dye 1~ \.= / \.C=3~ \.
~max in dichloromethane = 648 nm . C~3~C~3 f~ C~3/C~
Dve 2~ =CH- D~ /~=CH- ~ N/~
~max in dichloromethane = 632 nm fH3 Oe ClH3 ~0 _y~ 3: ~f ~ ~1 ~max in dichloromethane = 683 nm 0H 0~
Dye 4 (C2H5)2N~ N(~2~5)2 o ~ma~ in dichloromethane = 642 nm Oe Dye 5: ( CH ) N~ ~ --~ =N(3CH ) ./ ~ \. O ~/ ~ \.
.
.: .
, , 2~ 2 Dye 6: C2H5~ =CH~ =CH~ N-C2~5 11 ~0=9~
-~
Oe Dye 7: (C~3~N~ -C~ /-=CH-'- \ ~-~(CE3>2 N(CH3)2 N(C~3)2 ~Y~_ti /N~C~=C ~ \ r C~- \ _ /N C2~5 o~ Cl ~ 2H5 Dye j C} 3~ /-=C~ =C~
2~
Any dye can be used in the dye layer o~ the dye-donor element of the invention provided it is transferable to the dye-receiving layer by the action of heat. ~specially good reæults have been obtained with sublimable dyes. Examples of sublimable dyes include anthraquinone dyes, e.g., Sumikalon Violet RSTM (Sumitomo Chemical Co., Ltd.), Dianix Fast 8(3~
Violet 3R-FSTM (Mitsubishi Chemical Industries, Ltd.), and Kayalon Polyol Brilliant Blue N-BGMTM
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 KRTM (Nippon Kayaku Co., Ltd.), Sumickaron Diazo Black 5GTM (Sumitomo Chemical Co., Ltd.), and Miktazol Black 5GHTM (Mitsui Toatsu Chemicals, Inc.); direct dyes such as Direct Dark Green BTM
(Mitsubishi Chemical Industries, Ltd.) and Direct ~rown 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)(C~2C6~5) N~COCH3 (magenta) CN c~3 I-C - ~ I (yellow) O .
~.\ /o\ /CONHCH3 I ~ ~ (cyan) N \ _ / N(C2H5)2 or any of the dyes di~closed in U.S. Patent 4,541,830. The above dyes may be employed singly or Z
in combination to obtain a monochrome. The dyes may be 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 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(phenyleneoxide). The binder may be used at a coverage of from about 0.1 to about 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 such as cellulose acetate;
fluorine polymers such as polyvinylidene fluoride or poly(tetrafluoroethylene-co-hexafluoropropylene);
polyethers such as polyoxymethylene; polyacetals;
polyolefins such as polystyrene, polyethylene, polypropylene or methylpentane polymers. The support generally has 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 o~ 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 polyimide, a cellulose ester such as cellulose -~o-acetate, a poly(vinyl alcohol-co-acetal) or a poly(ethylene terephthalate). The support for the dye-receiving element may also be reflec~ive 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-~o-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 about 1 to about
such as cyclopentyl, t-butyl, 2-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m-tolyl;
or any of said Rl, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted car~ocyclic or heterocyclic ring, such as benzene, naphthalene, indole, indazoline or tetrahydroquinoline;
R5, R6! R7 and R8 each independently represents hydrogen, a substituted or .
unsubstituted alkyl or cycloalkyl group having from 1 to about 6 carbon atoms or an axyl or hetaryl group having from about 5 to :~
about 10 atoms such as cyclopentyl, t-kutyl, 2-ethoxyethyl, n-hexyl, benzyl, 3-chlorophenyl, 2-imidazolyl, 2-naphthyl, 4-pyridyl, methyl, ethyl, phenyl or m-tolyl;
or R5 and R6 or R7 and R~ may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring such as morpholine, pyrrolidine or piperidine; and n and m are each independently 1 to 4.
In a preferred embodiment of the invention, R5, R6, R7 and R8 are each ethyl. In another preferred embodiment, R5 and R6 are joined ~ogether to form a 5- to 7-membered nitrogen~containing heterocyclic ring and R7 and R8 are jolned together to form a 5- to 7-membered nitrogen-containing heterocyclic ring. In still another preferred embodiment, Rl and R2 are joined to~ether to form a benzene ring. In another pre~erred embodiment, Rl and R5 are joined together to form an indole ring and R4 and R7 are : joined together to form an indolium ring.
~ ~ ~b~ ~
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 0.05 to about 0,5 g/m2 within the dye layer.
The above infrared absorbing dyes m~y be synthesized by procedures similar those described in Dyes & Pigment , 9, 85-107 (1988).
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 deæired.
Dyes included within the scope of the invention include the following:
. ' ~
:
Dye 1~ \.= / \.C=3~ \.
~max in dichloromethane = 648 nm . C~3~C~3 f~ C~3/C~
Dve 2~ =CH- D~ /~=CH- ~ N/~
~max in dichloromethane = 632 nm fH3 Oe ClH3 ~0 _y~ 3: ~f ~ ~1 ~max in dichloromethane = 683 nm 0H 0~
Dye 4 (C2H5)2N~ N(~2~5)2 o ~ma~ in dichloromethane = 642 nm Oe Dye 5: ( CH ) N~ ~ --~ =N(3CH ) ./ ~ \. O ~/ ~ \.
.
.: .
, , 2~ 2 Dye 6: C2H5~ =CH~ =CH~ N-C2~5 11 ~0=9~
-~
Oe Dye 7: (C~3~N~ -C~ /-=CH-'- \ ~-~(CE3>2 N(CH3)2 N(C~3)2 ~Y~_ti /N~C~=C ~ \ r C~- \ _ /N C2~5 o~ Cl ~ 2H5 Dye j C} 3~ /-=C~ =C~
2~
Any dye can be used in the dye layer o~ the dye-donor element of the invention provided it is transferable to the dye-receiving layer by the action of heat. ~specially good reæults have been obtained with sublimable dyes. Examples of sublimable dyes include anthraquinone dyes, e.g., Sumikalon Violet RSTM (Sumitomo Chemical Co., Ltd.), Dianix Fast 8(3~
Violet 3R-FSTM (Mitsubishi Chemical Industries, Ltd.), and Kayalon Polyol Brilliant Blue N-BGMTM
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 KRTM (Nippon Kayaku Co., Ltd.), Sumickaron Diazo Black 5GTM (Sumitomo Chemical Co., Ltd.), and Miktazol Black 5GHTM (Mitsui Toatsu Chemicals, Inc.); direct dyes such as Direct Dark Green BTM
(Mitsubishi Chemical Industries, Ltd.) and Direct ~rown 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)(C~2C6~5) N~COCH3 (magenta) CN c~3 I-C - ~ I (yellow) O .
~.\ /o\ /CONHCH3 I ~ ~ (cyan) N \ _ / N(C2H5)2 or any of the dyes di~closed in U.S. Patent 4,541,830. The above dyes may be employed singly or Z
in combination to obtain a monochrome. The dyes may be 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 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(phenyleneoxide). The binder may be used at a coverage of from about 0.1 to about 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 such as cellulose acetate;
fluorine polymers such as polyvinylidene fluoride or poly(tetrafluoroethylene-co-hexafluoropropylene);
polyethers such as polyoxymethylene; polyacetals;
polyolefins such as polystyrene, polyethylene, polypropylene or methylpentane polymers. The support generally has 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 o~ 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 polyimide, a cellulose ester such as cellulose -~o-acetate, a poly(vinyl alcohol-co-acetal) or a poly(ethylene terephthalate). The support for the dye-receiving element may also be reflec~ive 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-~o-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 about 1 to about
5 glm2.
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 element of the invention may be used in sheet form or in a continuous roll or ribbon. If a continuous roll or ribbon is emp~oyed, it may have only one dye or may have alternating areas of other different dyes, such as sublimable oyan and/or magenta and/or yellow and/or black or other dyes. Such dyes are disclosed in U. S. Patents 4,541,830; 4,69~,651; 4,695,287; ~,701,439;
4,757,046; 4,743,582; 4,769,360; and 4,753,922.
Thust one-, two-, three- or four-color elements (or higher numbers also~ are included within the scope of the invention.
In a preferred embodiment of ths invention, the dye-donor element comprises a poly(ethylene terephthalate) support coated with sequentia~
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 transfer 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 offer substantial advanta~es in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation. In practice, 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 converslon. Thus, 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 trans~er dye from the dye-donor elements of the invention are available commercially. There can be employed, for 30 e~ample, Laser Model SDL-2420-~2TM from Spectrodiode Labs, or Laser Model SLD 304 V/WTM
from Sony Corp.
A thermal dye transfer assemblage of the invention comprises a) a dye-donor element as de~cribed above, and b) a dye-receiving element as described above, - , .~., . -., ,. ~ :
' the dye-receiving element being in a superpoæed 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 receiYing element.
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.
When a three-color image is to be obtained, the above assemblage is formed on three occa~ions 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 i~ provided to illus~rate 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 acetate propionate binder (2.5% acetyl, 45% propionyl) (0.27 g/m ) coated from methylene chloride.
A control dye-donor element was made as above containing only the magenta imaging dye.
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 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-~2 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 of dye transfer to the receiver was 6 x 6 mm. The power level of the laser was approximately 180 milliwatts and the exposure energy, including overlap, was 0.1 ergs per square micron.
The Status A green reflection density of each transferred dye area was read as follows:
Table 1 Infrared Status A Green Density in Donor Tranæferre!d to Receiver None (control) 0.0 Dye 1 0.~2 Dye 2 0.08 Dye 3 0.18 The above results indicate that 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 and scope of the invention.
~' '' ' ':
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 element of the invention may be used in sheet form or in a continuous roll or ribbon. If a continuous roll or ribbon is emp~oyed, it may have only one dye or may have alternating areas of other different dyes, such as sublimable oyan and/or magenta and/or yellow and/or black or other dyes. Such dyes are disclosed in U. S. Patents 4,541,830; 4,69~,651; 4,695,287; ~,701,439;
4,757,046; 4,743,582; 4,769,360; and 4,753,922.
Thust one-, two-, three- or four-color elements (or higher numbers also~ are included within the scope of the invention.
In a preferred embodiment of ths invention, the dye-donor element comprises a poly(ethylene terephthalate) support coated with sequentia~
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 transfer 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 offer substantial advanta~es in terms of their small size, low cost, stability, reliability, ruggedness, and ease of modulation. In practice, 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 converslon. Thus, 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 trans~er dye from the dye-donor elements of the invention are available commercially. There can be employed, for 30 e~ample, Laser Model SDL-2420-~2TM from Spectrodiode Labs, or Laser Model SLD 304 V/WTM
from Sony Corp.
A thermal dye transfer assemblage of the invention comprises a) a dye-donor element as de~cribed above, and b) a dye-receiving element as described above, - , .~., . -., ,. ~ :
' the dye-receiving element being in a superpoæed 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 receiYing element.
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.
When a three-color image is to be obtained, the above assemblage is formed on three occa~ions 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 i~ provided to illus~rate 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 acetate propionate binder (2.5% acetyl, 45% propionyl) (0.27 g/m ) coated from methylene chloride.
A control dye-donor element was made as above containing only the magenta imaging dye.
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 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-~2 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 of dye transfer to the receiver was 6 x 6 mm. The power level of the laser was approximately 180 milliwatts and the exposure energy, including overlap, was 0.1 ergs per square micron.
The Status A green reflection density of each transferred dye area was read as follows:
Table 1 Infrared Status A Green Density in Donor Tranæferre!d to Receiver None (control) 0.0 Dye 1 0.~2 Dye 2 0.08 Dye 3 0.18 The above results indicate that 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 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 squarylium dye which is located in the dye layer.
2. The element of Claim 1 wherein said squarylium dye has the following formula:
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
3. The element of Claim 2 wherein R5 R6, R7 and R8 are each ethyl.
4. The element of Claim 2 wherein R5 and R6 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring and R7 and R8 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring.
5. The element of Claim 2 wherein R1 and R2 are joined together to form a benzene ring.
6. The element of Claim 2 wherein R1 and R5 are joined together to form an indole ring and R4 and R7 are joined together to form an indolium ring.
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 squarylium dye which is located in the dye layer.
9. The process of Claim 8 wherein said squarylium dye has the following formula:
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring: and n and m are each independently 1 to 4.
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, 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 said R1, R2, R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring: and n and m are each independently 1 to 4.
10. The process of Claim 9 wherein R5, R6, R7 and R8 are each ethyl.
11. The process of Claim 9 wherein R5 and R6 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring and R7 and R8 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring.
12. The process of Claim 9 wherein R1 and R are joined together to form a benzene ring.
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 thereof a dye image-receiving layer, said dye-receiving element being in a superposed relationship with aid 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 squarylium dye which is located in the dye layer.
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 thereof a dye image-receiving layer, said dye-receiving element being in a superposed relationship with aid 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 squarylium dye which is located in the dye layer.
The assemblage of Claim 14 wherein said squarylium dye has the following formula:
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, halogen, cyano, alkoxyl aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of said R1, R2 R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
wherein:
R1, R2, R3 and R4 each independently represents hydrogen, hydroxy, halogen, cyano, alkoxyl aryloxy, acyloxy, aryloxycarbonyl, alkoxycarbonyl, sulfonyl, carbamoyl, acyl, acylamido, alkylamino, arylamino or a substituted or unsubstituted alkyl, aryl or hetaryl group;
or any of said R1, R2 R3 or R4 groups may be combined with R5, R6, R7 or R8 or with each other to form a 5- to 7-membered substituted or unsubstituted carbocyclic or heterocyclic ring;
R5, R6, R7 and R8 each independently represents hydrogen, 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 R5 and R6 or R7 and R8 may be joined together to form a 5- to 7-membered substituted or unsubstituted nitrogen-containing heterocyclic ring; and n and m are each independently 1 to 4.
16. The assemblage of Claim 15 wherein R5, R6, R7 and R8 are each ethyl.
17. The assemblage of Claim 15 wherein R5 and R6 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring and R7 and R8 are joined together to form a 5- to 7-membered nitrogen-containing heterocyclic ring.
18. The assemblage of Claim 15 wherein and R2 are joined together to form a benzene ring.
19. The assemblage of Claim 15 wherein and R5 are joined together to form an indole ring and R4 and R7 are joined together to form an indolium ring.
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 |
|---|---|---|---|
| US366,952 | 1989-06-16 | ||
| US07/366,952 US4942141A (en) | 1989-06-16 | 1989-06-16 | Infrared absorbing squarylium dyes for dye-donor element used in laser-induced thermal dye transfer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2018042A1 true CA2018042A1 (en) | 1990-12-16 |
Family
ID=23445318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002018042A Abandoned CA2018042A1 (en) | 1989-06-16 | 1990-06-01 | Infrared absorbing squarylium dyes for dye-donor element used in laser-induced thermal dye transfer |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4942141A (en) |
| EP (1) | EP0403930B1 (en) |
| JP (1) | JPH0326593A (en) |
| CA (1) | CA2018042A1 (en) |
| DE (1) | DE69006547T2 (en) |
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| JPS61260038A (en) * | 1985-05-15 | 1986-11-18 | Mitsubishi Chem Ind Ltd | Squarylium compound |
| JPS61218551A (en) * | 1985-03-23 | 1986-09-29 | Mitsubishi Chem Ind Ltd | Squarylium compound |
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| JPS61238755A (en) * | 1985-04-16 | 1986-10-24 | Mitsubishi Chem Ind Ltd | Squarylium compound |
| JPS62432A (en) * | 1985-06-27 | 1987-01-06 | Mitsubishi Chem Ind Ltd | Squarylium compound |
| JPH075551B2 (en) * | 1985-06-27 | 1995-01-25 | 三菱化学株式会社 | Squarylium compound |
| JPH0678285B2 (en) * | 1985-12-11 | 1994-10-05 | 三菱化成株式会社 | Squarylium compound and optical recording medium containing the compound |
| JPS62158779A (en) * | 1986-01-04 | 1987-07-14 | Fuji Photo Film Co Ltd | Infrared absorptive composition |
| JPS62299380A (en) * | 1986-06-18 | 1987-12-26 | Dainippon Printing Co Ltd | Transfer sheet |
| JPS63319191A (en) * | 1987-06-23 | 1988-12-27 | Showa Denko Kk | Transfer material for thermal recording |
| US4833123A (en) * | 1987-10-08 | 1989-05-23 | Sumitomo Chemical Company Limited | Yellow dye-donor element used in thermal transfer and thermal transfer and thermal transfer sheet using it |
-
1989
- 1989-06-16 US US07/366,952 patent/US4942141A/en not_active Expired - Lifetime
-
1990
- 1990-06-01 CA CA002018042A patent/CA2018042A1/en not_active Abandoned
- 1990-06-12 EP EP19900111078 patent/EP0403930B1/en not_active Expired - Lifetime
- 1990-06-12 JP JP2153840A patent/JPH0326593A/en active Granted
- 1990-06-12 DE DE1990606547 patent/DE69006547T2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4942141A (en) | 1990-07-17 |
| DE69006547T2 (en) | 1994-08-18 |
| JPH0326593A (en) | 1991-02-05 |
| JPH0512156B2 (en) | 1993-02-17 |
| DE69006547D1 (en) | 1994-03-24 |
| EP0403930A1 (en) | 1990-12-27 |
| EP0403930B1 (en) | 1994-02-09 |
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