CA1254744A - Cyan dye-donor element used in thermal dye transfer - Google Patents

Cyan dye-donor element used in thermal dye transfer

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Publication number
CA1254744A
CA1254744A CA000524523A CA524523A CA1254744A CA 1254744 A CA1254744 A CA 1254744A CA 000524523 A CA000524523 A CA 000524523A CA 524523 A CA524523 A CA 524523A CA 1254744 A CA1254744 A CA 1254744A
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Canada
Prior art keywords
dye
substituted
cyan dye
carbon atoms
cyan
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.)
Expired
Application number
CA000524523A
Other languages
French (fr)
Inventor
Steven Evans
Kin K. Lum
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
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Publication of CA1254744A publication Critical patent/CA1254744A/en
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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382Contact thermal transfer or sublimation processes
    • B41M5/385Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/39Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/913Material designed to be responsive to temperature, light, moisture
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/914Transfer or decalcomania
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/146Laser beam
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/24Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24802Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
    • Y10T428/24893Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including particulate material
    • Y10T428/24901Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] including particulate material including coloring matter
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31786Of polyester [e.g., alkyd, etc.]

Abstract

CYAN DYE-DONOR ELEMENT USED
IN THERMAL DYE TRANSFER
Abstract of the Disclosure A cyan dye-donor element for thermal dye transfer comprisea a support having thereon a cyan dye dispersed in a polymeric binder, the cyan dye compriaing a 2-carbamoyl-4-[N-(p-substituted amino-aryl)imino]-1,4-naphthoquinone.
In a preferred embodiment, the cyan dye has the formula:

Description

~474~L

CYAN DYE-DONOR ELEMENT USED
IN THERMAL DYE TRANSFER
This invention relstes to cysn dye-donor elements used in thermal dye trsn~fer which hsve good hue and dye stability.
In recent year~, thermal trsnsfer systems hsve been developed to obtain print~ from pictures which have been generatsd electronicslly from ~ color video camera. According to one wsy of obtaining such prints, an electronic picture is first sub~ected to color separation by color filters. The re3pective color-separsted images ~re then converted into elec-trieal signsls. These 3ignals are then operated on to produce cyan~ magenta and yellow electrical sig-nals. These qignals sre then transmitted to a ther-msl printer. To obtain the print, a cyan, magenta or yellow dye-donor element i~ pl~ced face-to-face with a dye-receiving element. The two sre then inserted between a thermal printing hesd and a platen roller.
A line-type thermal printing head is used to spply heat from the back of the dye-donor sheet. The therm~l printing head has many heating elements and i~ heated up sequentislly in response to the cyan, magenta and yellow signals. The process is then repeated for the other two colors. A color hard copy is thus obtained which corresponds to the original plcture viewed on 8 screen. Further det~ils of this process snd an spparstus for carrying it out are contained in U.S. Patent No. 4,621,271 by Brownstein entitled "Appar~tus and Method For Controlling A
Thermal Prlnter Apparatus," i~ued November 4, 1986.
A problem hss existed with the use of certain dyes in dye-donor elements for thermal dye tran~fer printing. Msny of the dye~ proposed for use ',`,.

, ::
, .

~ ~iax7~4
-2-do not have adequste st~b~lity to light. Others do not h~ve good hue. It would be desirable to provide cyan dyes which hsve good light ~tability ~nd h~ve improved hue~.
European patent applicRtion 147,747 relates to a dye-receiving element for thermal dye transfer printin~. It ~130 h~s a general disclosure of dyes for dye-donor elements useful therewith. Included within this general disclosure i~ ~ de~cription of sn indo~niline dye produced by the oxidation cvupling reaction of ~ p-phenylenedi~mine deriv~tive with phenol or naphthol. No ~pecific naphthol compounds are illustrated.
Substanti~l improv~ments in light stability ~nd hues are schieved in ~ccord~nce with this inven-tion which comprises ~ cysn dye-donor element for therm~l dye trsnsfer comprising A support bearing a dye lsyer comprising 8 cyan dye disper ed ~n a poly-meric binder, s~id cysn dye compri~ing a 2-carb-amoyl-4-~N~ substituted aminosryl)imino3-1,4-naphthoquinone.
In R preferred embodiment of the invention, the cy~n dye hss the following formula O
4 ~ ~./ ~ /
R - - t - I! I! R3 N-.~ t ~. NRlR2 =
wherein Rl, R2, and R5 are substituted or unsubstituted ~lkyl of from 1 to about 6 carbon atomq such ~s methyl, ethyl, propyl, i~opropyl, butyl, pentyl, hexyl, m2thoxyethyl, benzyl, 2-meth~nesulfon--amidoethyl, 2-hydroxyethyl, 2-cyanoethyl, methoxy-csrbonylmethyl, etc.; ~ubstituted or unsubstituted cyeloslkyl of from 5 to about 7 c~rbon stoms ~uch a~
cyclohexyl, cyclopentyl, etc.; substituted or unau~-~5~
~tituted Hryl of from ~bout 5 ~o ~bout 10 carbon stoms such ~s phenyl, pyridyl, naphthyl, p-tolyl, p-chlorophenyl, m-(N-methyl sulfamoyl)phenyl, etc ;
and S R3 and R4 are hydrogen; substituted or un~ub~tituted alkyl of from 1 to ~bout 6 carbon atoms ~uch a~ methyl, ethyl, propyl, i opropyl, butyl, pentyl, hexyl, methoxyethyl, 2-cyanoethyl, ben~yl, 2-hydroxyethyl, 2-methanesulfonamidoethyl, etc~;
halogen such a~ chlorine, bromine, or fluorine;
-NHCORl or -NHS02Rl.
Compounds included within the scope of the invention include the following:

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s ~ ~ ~ m ~
S T S ~ 'T TO = C,) ~ ~ I I I I I 1 2 ~n I
2 0 I /~ \ T ~ S S T T ~ I S
Z t~ o ~ ~ N

O =~ Q=Z
S

2 5 ~ ~ s Z O O
e:¦' T S S
V ~) S T I I :C I ~ I T

o o E _Ic~l ~ el Ln ~ ~ c~
o .
.n ~ C~
--~ O
T
~ N T Lt~
~n I T ¦ V t~ T ~ T 3 C

o T
~Y ¦ T ~ T I L~ I I X T

1 5 ~
T I I I T O
~> v ~ v ~) tn T ~ T

2 0 U~
:~ I I ~ I -r T I S
C`J ~~ C~l N ~

o z ~:
O O
:1: I I I T ~1 T

O o O
Q Z
E

-6- ~2~47~
A dye-barrier lsyer may be employed in the dye-donor elements of the invention to improve the density of the transferred dye. Such dye-~arrier layer material~ include hydrophilic m~terials such as those de~cribed and claimed in U.S~ Patent No.
4,716,144 entitled "Dye-Barrier and Subbing Layer for Dye-Donor Element U~ed in Thermal Dye Transfer" by Vanier, ~,um and Bowman, i~ued December 2~, 1987.
The dye in the dye-donor element of the invention i~ dispersed in a polymeric binder such as a cellulose derivatlve, e.g., cellulose acetate hydrogen phthalate, cellulose acetste, cellulo~e acetate propionate, cellulose acetate butyrate, cell-ulose 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 a~ a gravure process.
Any ~aterial can be used as the support for the dye-~onor element of the invention provided it i8 dimensionally stQble and can withstand the heat of the therm~l printing heads. Such materials include polyester~ ~uch as poly(ethylene terephthalste);
polyamides; polycarbonates; glassine paper; condenser paper; cellulose esters such as cellulose acetate;
fluorlne polymers such as polyvinylidene fluoride or poly(tetrafluoroethylene-co-hexafluoropropylene);
polyethers such as polyoxymethylene; polyacetal~;
polyolefins such as polystyrene, polyethylene, polypropylene or methylpent~ne polymers; snd polyimides such aa polyimide-amides ~nd polyPther-imide~. The support generslly has ~ thickness of from about ~ to about 30 ~m. It may also be coated with Q subbing lsyer, lf de~ired.

~:25~

The re~erse side of the dye-donor element may be coated with a slipping layer to pre~ent the printing head from sticking to the dye-donor ele-ment. Such a slipping layer would cornprise a lub-ricating material such as a surface acti~e agent, aliquid lubricant, a solid lubricant or mixtures thereof, with or without a polymeric binder.
Preferred lubricating materials include oils or semi-crystalline organic solids that melt below lO~C
such as poly(~inyl stearate), beeswax, perfluorinated alkyl ester polyethers, poly(caprolactone), carbowax or poly(ethylene glycols). Suitable polymeric binders for the slipping layer include poly(~inyl alcohol-co-butyral), poly(uinyl alcohol-co-acetal), poly(styrene), poly(~inyl acetate), cellulose acetate butyrate, cellulose acetate or ethyl cellulose The amount of the lubricating material to be used in the slipping layer depends largely on the type of lubricating material, but is generally in the range of about .OOl to about 2 g~m . If a poly-meric binder is employed, the lubricating material is present in the range of O.l to 50 weight ~, prefer-ably 0.5 to 40, of the polymeric binder employed.
The dye-recei~ing element that is used with the dye-donor element of the inuention usually comprises a support hauing thereon a dye image-recei~ing layer. The support may be a transparent film such as a poly(ether sulfone), a polyimide~ a cellulose ester such as cellulose acetate, a poly(~inyl alcohol-co-acetal~ or a poly(ethylene terephthalate). The support for the dye-recei~ing element may also be reflectiue such as baryta-coated paper, white polyester (polyester with white pigment incorporated therein), an iuory paper, a condenser paper or a synthetic paper such as duPont Ty~ek~. In a preferred embodiment, polyester with a white pigmRnt incorporated therein is employed.

~L~5~

The dye image-receiving 18ye. may compr~e, for example, a polycarbonste, a polyurethane, R
polyester, polyvinyl chloride, poly(styrene-co-acrylonitrile~, poly(csprolsctone) or mixtures thereof. The dye lmsge-receiving layer may be present in ~ny amount which is effPctive for the intended purpose. In genersl, ~ood results have been obt~ined st a concentrstion of from ~bout 1 to about 5 glm2.
AY noted above, the dye-donor element~ of the invention are used to form 8 dye trsnsfer image.
Such a process comprises imagewiqe-heating a dye-donor element a~ described above and ~ransFerring a dye image to a dye-receiving element to form the dye trsnsfer image.
The dye-donor element of the invention may be used in 3heet form or in a continuous roll or ribbon. If a continuous roll or ribbon is employed, it msy have only the cysn dye thereon as described sbove or msy have slternQting areas of other dif-ferent dyes, such as sublimable magenta and/or yellow and/or black or other dyes. Such dyes sre disclosed in U.S. Patent 4,541,830. Thus, one-, two-, three- or four-color elements (or higher numbers also) Are included within the acope of the invention.
In a preferred embodiment of the invention, the dye-donor element comprises a poly~ethylene terephthslate3 ~upport costed with sequential repeating areas of magenta, yellow snd the cyan dye ~s described above, and the ~bove process step~ are sequentially performed for each color to obt~in a three-color dye tran~fer image. Of course, when the process is only per~ormed for a single color, then a mono~hrome dye trsnsfer image is obtained.

~25~7~
Thermal printing head~ which can be used to transfer dye from the dye-donor elements of the invention are available commercially. There can be employed, for exsmple t 8 Fu~itsu Thermsl Head (FTP-040 MCSO01~), a TDK Thermal Head F415 HH7-1089~ or a Rohm Thermal Head KE 20~8-F30.
A thermal dye transfer assemblage of the invention comprises a) ~ dye-donor element as described above, and b) a dye-receivin~ element as described above, the dye-receiving element bein~ in a superposed relstionship with the dye-donor element so that the dye layer of the donor element is in contact with the dye image-receiving layer of the receiving element.
The above assembla~e comprising these two elements may be prea~sembled a~ an integral uni-t when a monochrome image is to be obtained. This may be done by temporarily sdhering the two elements to-gether at their margins. After transfer~ the dye-receiving element is then peeled apart to reYeal the dye transfer image.
When a three-color imsge is to be obtained, the above assemblage is formed on three occasions durin~ the time when heat is applied by the thermal printing head. 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 brou~ht ln register with the dye-receiving element and the process repeated.
The third color is obtained in the same manner.
The following examples ~re proYided to illustrate the invention.

. ~, ,, ~L2S~7~4 -~o-ExamPle 1 A) A cyan dye-donor element was prepsred by coating the following layers in the order recited on a 6 ~m poly(ethylene terephthalate) support:
1) Dye-barrier layer of gelatin nitrate (gelstin, cellulose nitrate snd salicylic acid in approximately 20:5:2 weight rat~o in a 301vent of acetone, methanol snd water) (0.33 g/m ), 2) Dye layer containing a cysn dye as identi--fied below (0.27 g/m2~ in cellulose acetste hydrogen phthalate (0.41 g/m2) coated from an acetonef2-butsnone/cyclo-hexanone solvent.
On the back side of the element, a slipping layer of poly(vinyl stesrate) (0.76 glm2) in cellulose acetate butyrate ~0.33 g/m2) W8S coated from tetrshydrofuran solvent.
B) A ~econd cy~n dye-donor elem~nt wa~
prepared by coating the following layers in the order recited on a 6 ~m poly(ethylene terephthalate) suppo~t:
l) Dye-barrfer layer of gelatin nitrst0 (gela-tin and cellulose nitrate in spproximately 2:1 weight ratio in a solvent of primsrily acetone and methanol) (0.20 g~m ) coated from an scetone and water ~olvent, 2) Dye layer contsining a cysn dye as identi--fied below (0.37-0.3~ g/m2) in cellulose acetate (C.41-0.43 g/m2) costed from an acetone/2-butanone/cyclohexanone solvent.
On the back side of the element, a slipping layer of poly(vinyl stesrate) (0.31 8/m ) in cellulose acetate butyrste (0.46 g/m2) was coated from 5 tetrahydrofuran solvent.
The following cyan dyes were evaluated:

,i . ~, , 254L74a~

Compound 1 f It r,3 \ _ / 2 5 2 Compound ~ CONHCH3 N~ -N(C H ) l _ /N2 Control Compound l CF3-C- El~ ,'i -N-N~ -N(C2H5)2 ~HCOCF3 1 - q~ 2 Control Compound 2 NO / ~S/ N N ~ ~--N(C2H5)2 ~HCOCH3 ~ 2 C,H3 Control Compound 3 I/ ~ / N N-t ll ~t/CH3 CF3C CSH CONH/ ~/ ~ \CH

O

Control Compound 4 i~ \il/ \il N - ~ ~ - N(C2H5)2 ~2547~

Dye-receiving element~ were prepsred by co~ting a solution of Makrolon 5705~ ~Bay~r A.G.
Corpor~tion) polycsrbonate re~in (2.9 glm2~ in a methylene chloride snd trichloroethylene solvent mixture on ~n ICI Melinex 990~ white polyester ~upport for density evsluation~ or on a transparent poly(ethylene terephthalate film ~uppport for spec-trsl absorption evalustions.
The dye slde of the dye-donor element strip 0.75 inches (19 mm) wide was placed in cont~ct with the dye 1mage-receiving l~yer of the dye-receiver element of the s~me width. The assemblage was fastened in the ~sws of a stepper motor driven pull-ing device. The assembl~e w~s laid on top of a 0.55 (14 mm) diameter rubber roller and a Fu~itsu Thermal Head (FTP-040MCS001~) ~nd was pressed with a spring ~t a force of 3.5 pounds (1.6 kg) against the dye-donor element side of the a~semblage pushing it against the rubber roller.
The imaging electronics were ~ctiv~ted C8U3-in~ the pulling device to draw the ~ssembl~ge between the printing head and roller at 0.123 inches/~ec (3.1 mm/Rec). Coincident~lly, the re~istive elements in the thermsl print he~d were heated st 0.5 msec incre-ments from 0 to 4.5 msec to generste 8 grQdU8ted density teRt pattern. The voltage supplied to the print head wss approximately 19 v representing ap-proxi~tely 1.75 wstts/dot. E~timated head tempers-ture wss 250-400C.
The dye-receiving element W8~ ~eparsted from the dye-donor element and the Status A red reflection den~ity of the step image was read. The im~ge w~s then sub~ected to "HI~-f~ding": 4 d~ys, 50 kLux, 5400K, 32C, ~pproximately 25~ RH. The density loss ~t ~ density ne~r 1.0 w~s calcul~ted.
The following dye st~bility data were obtained:

~2~;~7~

Table 1 _.
~D (at initial Dye Donor Format 1.0 densitY) S Compound l B -0.07 Compound 2 B -0.07 Control 1 Q -0.27 Control 2 ~ -0.46 Control 3 ~ -0.62 l~ Control 4 ~ -0.22 Use of the compounds in accordance with the inuention showed superior light stability as compared to a ~ariety of control dyes.
The light absorption spectra from 400 to 700 nm were also obtained after transfer of an area of the dye to the transparent support receiver in the ~anner indicated aboue. From a computer normalized 1.0 density cur~e, the ~-max, and HBW (half-band width =width of the dye absorption enuelope at one-half the maximum dye density) were calculated.
The following results were obtained:

Table 2 Dye ~-max HBW
Compownd l 669 137 Compound 2 686 107 Control 1 622 121 Control 2 641 121 Control 3 653 107 Control 4 597 132 The dyes of the inuention are o~ good cyan hue and all ha~e ~-max's in the desired region of beyond 660 nm. The control dyes ha~e ~-max's at shorter wauelengths or pronounced shoulders on the short wauelength side of the spectral curues and thus tend to look too blue.

~547~

Example 2 A) A cysn dye-donor element wa~ prepared by coating the following layers in the order recited on ~ 6 ~m poly(ethylene terephthalste) 3upport:
1) Dye-berrier layer of poly(acrylic)acid ~0.16g/m2) coated from water, and 2) Dye layer containing a cysn dye a9 identi-fied in Table 3 below (0.77 mmoles/m2) in 8 cellulose acetate (40% acetyl~ binder ~1.2 g/g of dye) coated from a 2-butanone solvent On the back side of the element W85 coated a slipping layer the type di~closed in U.S. Patent No. 4,717,711 of Vanier et al, issued January 5, 1988.
Dye-receiving elements were prepared as in Example l.
The dye side of ths dye-donor element strlp one inch (25 mm) wide was placed in contact with the dye image-receiving layer of the dye-receiver element of the same width. The assemblage was fastened in the ~aw~ of a ~tepper motor driven pulling device.
The ~semblsge was laid on top of a 0.55 (14 mm) diameter rubber roller and a TDK Thermal Head L-133~ (No. C6-0242) and wa~ pressed with a spring ~t 8 force of 8 pounds (3.~ kg~ against the dye-donor element side of the assemblage pu-~hing it again~t the rubber roller.
The imaging electronics were activated caus-ing the pulling device to draw the assemblage between the printing he~d and roller at 0.123 inehes/sec (3.1 mm/sec). Coincidentally, the re~istive elements in the thermAl print head were heated at increments from 0 up to 3.3 msec to generate a graduated density test p~ttern. The voltage ~upplied to the print head was approximately 21 v representing approximately 1.7 watt~/dot (12 mjoules/dot).

.

~;4744 The dye-recei~ing element was separated from the dye-donor element and the Statws ~ red reflection density of the step image was read. The image was then subjected to "HID-fading": 7 days, 50 kLux, 5400K, 32C, approximately 25% RH. The % density loss at maximum density was calculated.
The following dye stability data were obtained:

Table 3 % Density Loss Dve From D-max Compound 10 8 Compound 11 9 Compound 12 10 Compownd 13 Compound 14 6 Compound 15 5 Compound 16 8 Compound 17 9 Compound 18 Compound 19 25 Control 4 14 With the exception of Compound 19, the cyan dyes of the inuention show superior light stability as compared to the control compound.
The light absorption spectra were obtained and the ~-max and HBW were obtained as in Example 1 with the following results:

7~

Table 3 ~-max HBW
~ Y~ ___ (nm) (nm~
Compound 10 669 137 Compound 11 6S4 127 Compound 12 662 128 Compound 13 655 128 Compound 14 697 13~
Compownd 15 705 142 Compound l& 687 134 Compound 17 684 1~9 Compound 18 659 139 Compound 19 680 128 Control 4 597 132 The cyan dyes of the in~ention are of good cyan hue and each has ~-max beyond 650 nm. The control dye had a ~-max less than 600 nm and thus tends to look too blue.

xample 3 Preparation of Compound 1 N-(p-diethylamino)phenyl-2-(N-methyl)carbamoyl-1,4-naphthoquinone ~ solution of 2-(N-methylcarbamoyl~
naphthol (20.1 g, 0.1 mole) in 1000 mL ethyl acetate was mixed with a solution of N,N-diethyl-p--phenylene-diamine hydrochloride (20.1 9, 0.1 mole) in 500 mL of distilled water. The two-phase system was rapiclly stirred while solid sodium carbonate ~106 ~, l.0 mole) was added in portions. Then a solution of 164.5 9 (0.5 mole) potassium ferricyanide in 500 mL
distilled water was added dropwise o~er 30 minutes.
The reaction was stirred 16 hours at room temperature and then filtered through a pad of diatomaceous earth.
The filtrate was transferred to a separatory funnel, the layers separated and the or~anic phase ~25~L4 washed three times with distilled water. The organic ph~se was dr~ed over msgnesium ~ulfate and pa~sed over a short (3 inch diameter x 2 inch height) column of silica gel (Woelm TSC~) snd evspor~ted to dryne3~. Cryst~llization of the crude product from ~50 mL of methanol y~elded 28.5 g (78.9% of theory) of a blue solid, m.p. 127- 128Cn The invention has been described in detail with p~rticular 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)

WHAT IS CLAIMED IS:
1. A cyan dye-donor element for thermal dye transfer comprising a support bearing a dye layer comprising a cyan dye dispersed in a polymeric bin-der, said cyan dye comprising a 2-carbamoyl-4-[N-(P-substituted aminoaryl)amino]-1,4-naphthoquinone.
2. The element of Claim 1 wherein said cyan dye has the formula:
wherein R1, R2, and R5 are each inde-pendently substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; substituted or unsub-stituted cycloalkyl of from about 5 to about 7 carbon atoms; or substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; and R3 and R4 are each lndependently hydrogen;
substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; halogen; -NHCOR1 or -NHSO2R1.
3. The element of Claim 2 wherein R5 is methyl.
4. The element of Claim 2 wherein both and R2 are ethyl.
5. The element of Claim 2 wherein R4 is hydrogen and R3 is hydrogen or methyl.
6. The element of Claim 5 wherein R5 is methyl and both R1 and R2 are ethyl.
7. The element of Claim 2 wherein a dye-barrier layer is located between said dye layer and said support.
8. The element of Claim 1 wherein the side of the support opposite the side bearing said dye layer is costed with a slipping layer comprising a lubricating material.
9. The element of Claim 1 wherein said support comprises poly(ethylene terephthalate).
10. The element of Claim 1 wherein said dye layer comprises sequential repeating areas of magen-ta, yellow and said cyan dye.
11. In a process of forming a cyan dye transfer image comprising imagewise-heating a dye-donor element comprising a support bearing a dye layer comprising a cyan dye dispersed in a polymeric binder and transferring a cyan dye image to a dye-receiving element to form said cyan dye transfer image, the improvement wherein said cyan dye com-prises a 2-carbamoyl-4-[N-(p-substituted aminoaryl)-imino]-1,4-naphthoquinone.
12. The process of Claim 11 wherein said cyan dye has the formula:
wherein R1, R2, and R5 are each inde-pendently substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; substituted or unsub-stituted cycloalkyl of from about 5 to about 7 carbon atoms; or subtituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; and R3 and R4 are each independently hydrogen;
substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; halogen; -NHCOR1 or -NHSO2R1.
13. The process of Claim 11 wherein said support is poly(ethylene terephthalate) which is coated with sequential repeating areas of magenta, yellow and said cyan 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 cyan dye-donor element comprising a support bearing a dye layer comprising a cyan dye dispersed in a polymeric binder, and b) A dye-receiving element comprising a support bearing a dye image-receiving layer, said dye-receiving element being in a superposed relationship with said cyan dye-donor element so that said dye layer is in contact with said dye image-receiving layer, the improvement wherein said cyan dye comprises a 2-carbamoyl-4-[N-(p-substituted aminoaryl)imino]-1,4-naphthoquinone.
15. The assemblage of Claim 14 wherein said cyan dye has the formula:

wherein R1, R2, and R5 are each inde-pendently substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; substituted or unsub-stituted cycloalkyl of from about 5 to about 7 carbon atoms; or substituted or unsubstituted aryl of from about 5 to about 10 carbon atoms; and R3 and R4 are each independently hydrogen;
substituted or unsubstituted alkyl of from 1 to about 6 carbon atoms; halogen; -NHCOR1 or -NHSO2Rl.
16. The assemblage of Claim 15 wherein R5 is methyl.
17. The assemblage of Claim 15 wherein both R1 and R2 are ethyl.
18. The assemblage of Claim 15 wherein R4 is hydrogen and R3 is hydrogen or methyl.
19. The Assemblage of Claim 15 wherein both R1 and R2 are ethyl.
20. The assemblage of Claim 14 wherein said support of the dye-donor element comprises poly-(ethylene terephthalate).
CA000524523A 1985-12-24 1986-12-04 Cyan dye-donor element used in thermal dye transfer Expired CA1254744A (en)

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US81320985A 1985-12-24 1985-12-24
US813,209 1985-12-24
US911,839 1986-09-26
US06/911,839 US4695287A (en) 1985-12-24 1986-09-26 Cyan dye-donor element used in thermal dye transfer

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EP0227096A3 (en) 1988-07-27
US4695287B1 (en) 1990-03-27
US4695287A (en) 1987-09-22

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