US3788845A - Process for forming dye images - Google Patents

Process for forming dye images Download PDF

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Publication number
US3788845A
US3788845A US00256862A US3788845DA US3788845A US 3788845 A US3788845 A US 3788845A US 00256862 A US00256862 A US 00256862A US 3788845D A US3788845D A US 3788845DA US 3788845 A US3788845 A US 3788845A
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Prior art keywords
images
gelatin
sheet
dye
solvent
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US00256862A
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English (en)
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S Osawa
Y Tamai
M Takimoto
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G13/00—Electrographic processes using a charge pattern
    • G03G13/26—Electrographic processes using a charge pattern for the production of printing plates for non-xerographic printing processes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G13/00—Electrographic processes using a charge pattern
    • G03G13/01—Electrographic processes using a charge pattern for multicoloured copies

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  • the present invention relates to a color printing process based on a recording process utilizing electrostatic latent images such as an electrophotographic process and an electrostatic recording process, and especially to an improvement in a dye transfer process which comprises developing electrostatic latent images to convert them into gelatin images and utilizing the resulting gelatin relief.
  • the first method which is the most widely used, is of combining silver halide emulsions with color developing process.
  • the second one is a dye transfer process which comprises carrying out tanning development using silver halide emulsions and utilizing the resulting gelatin relief, which generally prevails as the technicolor process.
  • the former is suitable for a mass production.
  • the images obtained are insufficient in durability and especially in light-resisting properties.
  • the latter the dye transfer process
  • images which have extremely high durability can be obtained.
  • This dye transfer process closely approaches printing. Accordingly, a commercial profit is improved in a case of producing a large number of duplicates from one original. But it is not suitable for produc- 3,788,845 Patented Jan. 29, 1974 ICC ing a small number of duplicates, because the cost per a duplicate becomes particularly high.
  • a color printing process which comprises forming electrostatic latent images on an electrophotographic sensitive layer containing a photoconductive zinc oxide as the main photoconductor, changing the latent images into gelatin images using an electrophotographic developer containing a finely divided gelatin powder, and subjecting to the following treatments, that is, (A) removing the zinc oxide included in the electrophographic sensitive layer using an acid, (B) contacting the gelatin images with a dye solution containing a dye dissolved in a solvent mainly consisting of water to cause absorption of the dye into the gelatin images, (C) removing the excess dye solution on the gelatin images by washing with an acidic aqueous solution, and (D) contacting a layer which is capable of being readily dyed by the dye with the gelatin layer to transfer the dye to be caapble of being readily dyed layer.
  • Step (A) is
  • the binder resin layer forms a porous liquid storing layer.
  • the gelatin images are relatively easy to break, because they are supported on the binder layer which forms the liquid storing porous layer. Further, since the dye solution is occluded in the spaces of the liquid storing layer in the next Step (B), it is impossible to remove the absorbed dye solution by washing in Step (C). Thus, it has been confirmed in the dye transfer treatment of the Step (D) that unevenness of the image portion and fog of the non-image portion are caused.
  • a first object of the present invention is to produoe color prints easily and cheaply using the dye transfer process.
  • an object is to provide an improved dye transfer process in which a gelatin relief obtained by the electrophotographic process is utilized.
  • a second object is to provide a method for obtaining uniform distinct color images having a high image density but a low fog density using a dye transfer process in which the gelatin relief is obtained using the electrophotographic or electrostatic recording process.
  • a third object is to provide a process by which the printing durability is improved by reinforcing the gelatin relief.
  • FIG. 1 shows the state in which a photoconductive layer composed of a photoconductive substance 13 and an electrically insulating binder resin 14 applied on a support film 11 having a layer of a low electric resistivity 12 is developed with a gelatin toner 15.
  • FIG. 2 shows the state in which the photoconductive substance is removed by acid treatment of the photoconductive sheet.
  • the gelatin toner thereon shows a state that fixed previously by steam and then hardened.
  • FIG. 3 shows the state after the organic solvent treatment and evaporation of the solvent elements of the present invention.
  • FIG. 4 is a sectional view of an example of an apparatus for evaporating the organic solvent.
  • the sensitive layer carrying the electrostatic latent images is developed using an electroph-otographic developer containing a gelatin toner (for example, an electrophotographic liquid developer which contains a gelatin toner in a carrier liquid);
  • an electroph-otographic developer containing a gelatin toner for example, an electrophotographic liquid developer which contains a gelatin toner in a carrier liquid
  • the present invention involves washing with water after removing the photoconductor (for example, zinc oxide) using the acid and carrying out Steps (V) and (VI), that is, soaking the sheet having the binder resin layer which forms a liquid storing layer and carries the gelatin images thereon in the organic solvent, and contacting the sheet wetted 'by the solvent with a warmed metal plate having a flat surface so as to contact closely the support side of the sheet with the flat surface to evaporate rapidly the organic solvent.
  • Steps (IV), (V) and (VI) which are elements of the present invention, only images which have a comparatively heavy fog and unevenness are obtained. Furthermore, it has been found that printing durability of the gelatin relief is insufficient.
  • a powder of the photoconductive substance and the resin generally are mixed.
  • the mixture is then applied to a support and dried.
  • all surfaces of the particles of the photoconductive substance are not completely covered with the binder resin but the particles themselves contact each other through the binder resin to form a photoconductive layer. Consequently, the photoconductive particles are eroded gradually at the surface thereof and dissolve in the step of treating with the acid.
  • the acid are acetic acid and nitric acid.
  • the binder when this sheet is soaked in the organic solvent, the binder can be considered as slightly swollen. Then the organic solvent is rapidly removed by evaporation by which the slightly swollen binder resin is considered to form a continuous uniform film by heat at this time and by the function of the solvent. Accordingly, the binder resin layer subjected to the organic solvent treatment changes into a uniform film which loses the liquid storing property, by which adhesion of the gelatin forming the images to the support is improved and the mechanical strength of the film increases. Thus, the images obtained have a very low fog density and a very little unevenness, that is, distinct uniform images are finally obtained.
  • the electrophotographic sensitive element used in the present invention is one prepared by providing a sensitive layer composed of zinc oxide as the main photoconductor and an insulating resin on a water-resisting support.
  • Suit able insulating resins which can be used in the present invention include both thermo-setting resins and thermoplastic resins.
  • the thermo-setting resins may be those obtained by appropriately curing an alkyd resin, an epoxyester resin, an acrylic resin, a silicone resin and the like. The curing can be effected using any of the conventional procedures.
  • an alkyd resin containing a drying oil, an epoxyester resin and a silicone resin can preferably be cured by using oxygen and a metallic soap as a catalyst.
  • a typical procedure for curing the epoxyester resin is disclosed in US.
  • An alkyd resin, an epoxyester resin and an acrylic resin, each containing primary or secondary hydroxy groups, can preferably be cured with a polyisocyanate as disclosed in British patent specification No. 1,237,03 6.
  • the curing of the alkyd resin and the epoxyester resin can also be effected with a melamine resin, benzoguanamine or the like in accordance with the teaching in German Pat. OLS 2,100,926.
  • thermo-plastic resins include vinyl chloride/vinyl acetate copolymer, vinyl acetate/ acrylic ester copolymer, acrylic resin, polystyrene, styrene/butadiene copolymer, vinyl acetate/crotonic acid copolymer and the like. When these resins are used, it is preferred that the Mvent f tlhe resins has a weak solubilizing property.
  • the photoconductive materials which can be used together with the zinc oxide include CdS, CdSe, Cd(S,Se), ZnS, TiO anthracene, polyvinylcarbazole, carbazole derivatives, as well as CdS.nCdSO which is disclosed in German patent publication No. OLS 2,028,121.
  • Examples of inorganic photoconductive materials are enumerated in US. Pat. No. 3,121,006.
  • the photoconductive materials may be those which do not adversely affect the dye transfer of the dyestuff for dye transfers even if they are not soluble in acids.
  • the support have water-resisting properties and acid resisting properties, because the acid treatment is practiced in order to remove the zinc oxide.
  • the support triacetyl cellulose films, polyethylene terephthalate films, and polycarbonate films are especially preferred.
  • a layer having a low electric resistivity is usually provided between the above described sensitive layer and the support. Therefore, it is suitable to choose a layer having the low electric resistivity 'which does corrode quickly due to the acid treatment.
  • the organic solvent used in the present invention should not dissolve gelatin, the Water resisting support or the binder resin. Further, it is preferred to have a boiling point of less than 150 C., because if the boiling point is too high, the sheet must be heated at a high temperature to remove the solvent.
  • the binder resin is a thermosetting resin
  • the following organic solvents are preferably used. Namely, methanol, ethanol, isopropyl alcohol, methyl acetate, ethyl acetate, diethylketone, toluene, benzene, xylene and cyclohexane etc. are suitable for use. These solvents have a boiling point above 30 C. and less than 150 C. and an evaporation rate greater than 50, based on the evaporation rate of n-butyl acetate being 100, as shown by the following:
  • the binder resin is a thermo-plastic resin
  • the resin used should not dissolve in the organic solvent.
  • ester type solvents and ketone type solvents are not suitable for use.
  • the organic solvents can be used alone or as mixtures of two or more thereof.
  • the sheet which has been subjected to acid treatment and Washing with water can be soaked in the water-miscible solvent, such as methanol, isopropyl alcohol, methyl acetate, ethyl acetate, diethylketone and the like, as illustrated above.
  • a water-miscible solvent such as methanol, ethanol, acetone or the like
  • the sheet which has been subjected to the acid treatment and washing with water is first soaked in water-miscible organic solvent so as to replace the water contained in the wetted sheet with the above water-miscible organic solvent (acetone being preferable), and the thus treated sheet is then soaked in an organic solvent which is miscible with the above watermiscible organic solvent as enumerated above.
  • the above replacement of water with the water-miscible organic solvent will not be necessary if the wetted sheet is dried directly after the washing with water.
  • the solvent used for the soaking will be determined depending upon the type of the binder used for the photoconductive layer.
  • the support side of the sheet is brought into close contact with the heating plate in order to evaporate the organic solvent.
  • the heating plate metal plates which are heat conductive such as those of stainless steel, copper, aluminum and iron plated or coated are preferably used.
  • a heat source for heating such a metal plate is steam or electrothermic wire, and it is preferable to use those for which the temperature of the heating plate can be easily controlled.
  • the temperature of the heating plate depends upon the types of organic solvents used,
  • a maximum of 60 C. above to a maximum of 20 C. below the boiling point of the solvent It has been found that a more preferred range of the temperature is from a maximum of 50 C. above to a minimum of 10 C. below the boiling point of the solvent. Still further, it is preferred to use a solvent having a boiling point of from about 30 to C.
  • the organic solvent should be evaporated at a temperature below the heat-resisting temperature of the sheet film of the support.
  • the sheet is heated at a temperature above the heat-resisting temperature thereof, the sheet is easily distorted and the flatness thereof is injured. This causes an uneven transfer at the dye transfer step making it impossible to obtain uniform images.
  • the evaporation of the organic solvent is not conducted rapidly when the heating temperature is too low, isolated uneven areas remain on drying and consequently ditficulty in dye transferring occurs too. As a result, the solvent should be evaporated uniformly, and rapidly.
  • FIG. 1 a part of the photoconductive sensitive layer developed with a gelatin toner (see British Pat. No. 1,255,762) is shown.
  • finely divided particles 13 of a photoconductive substance such as zinc oxide are applied to a support film 11 having a layer of a low electric resistivity 12 together with an insulating binder resin 14.
  • a gelatin toner image 15 adheres to the surface of the sensitive layer.
  • FIG. 2 the greater part of the photoconductive particles is removed by acid treatment, for example, with acetic acid or nitric acid to form a porous layer 25 which easily stores the dye solution.
  • a number of openings 27 exist in the layer.
  • the gelatin toner 26 is supported by only the binder resin layer 23. Although the photoconductive particles 24 covered with the binder resin 23 exist in a very small amount, they are not a hindrance to the subsequent treatments. In such a state, adhesion of the binder resin 23 to the gelatin toner 26 and to the support film 21 having a layer of low elecLric resistivity 22 is not sutficient and is mechanically wea
  • FIG. 3 shows the condition of the sensitive layer subjected to the organic solvent treatment and drying which are elements of the present invention.
  • the binder resin layer 33 supported on the support film 31 becomes a homogeneous continuous layer and the openings 27 shown in FIG. 2 have disappeared. Further, adhesion of the binder layer 33 to the gelatin toner 35 and to the layer having a low electric resistivity 32 is improved and the mechanical strength thereof increases. 34 are photoconductive particles surrounded completely by the binder resin 33, which do not hinder the dye transfer.
  • FIG. 4 shows an example of an apparatus for drying after soaking in the organic solvent.
  • Super heated steam is introduced into a heating box 41 made from metal plates through inlet 42 and outlet 43.
  • fins 45 are provided in order to improve conductivity and maintenance of the temperature.
  • a support film 47 having a binder resin and carrying toner images which has been treated with the organic solvent is brought into close contact with the fiat outer surface 46 of the heating box 41, and dried by holding it in contact using stoppers 44 at the four corners.
  • dyes used for transferring in the present invention acid dyes and mordant dyes are preferably used.
  • Suitable dyes are as follows:
  • Cyan dyes Color Index, Acid Blue 45 (CI. 63010), Acid Green 16 (Cl. 44025), Acid Green 1 (Cl. 10020), Acid Blue 1 (CI. 42045), Acid Blue 9 (CI. 42090) and Acid Blue 54 (no CI. number, anthraquinone dye).
  • Yellow dyes (Color Index), Acid Yellow 23 (Cl. 19140), Acid Yellow 11 (Cl. 18820), Acid Yellow 34 (CI. 18890) and Direct Yellow 12 (Cl. 24895).
  • the images obtained by the present invention have a high quality, an excellent light-resisting property and a good shade. Namely, deep colors are reproduced because there is no surface reflection in comparison with the images obtained electrophotographically using toners of each color. Further, faithful color reproduction is obtained, because each color of which multicolor images are composed is sufiiciently transparent and mixing of the colors can be carried out completely. Further, it is possible to make a number of prints by supplying the dye to the resulting images and transferring because the once obtained gelatin relief images can be used repeatedly many times.
  • the present invention is particularly effective where zinc oxide is used as the photoconductor in the electrophotographic sensitive layer. Further more, the invention is effective for the photoconductive layer where other photoconductors are used together with the zinc oxide.
  • Photoconductors which can be used together with the zinc oxide include CdS, CdSe, Cd(S,Se), ZnS, ZnSe, TiO anthracene, polyvinylcarbazole and carbazole derivatives. These photoconductors can be removed using acids from the sensitive layer together with the zinc oxide, or they do not disturb the dye transfer step if they remain in the sensitive layer.
  • EXAMPLE 1 5 g. of photographic use gelatin was added to 95 g. of distilled water. After 30 minutes, the gelatin was swollen. The mixture was then warmed at '60" C. to prepare a transparent aqueous gelatin solution.
  • Acetone 980 Cotton seed oil thus, a milk-white gelatin dispersion was obtained. To this dispersion, a solution having the following composition was added while stirring.
  • the resin component of this varnish was insoluble in acetone and soluble in a carrier liquid.
  • Kerosene was added for the purposes of lowering the evaporation rate of the liquid developer. It was found that the gelatin toner in the liquid developer had a positive charge.
  • a homogeneous coating solution was prepared by adding 100 parts by weight of photoconductive zinc oxide and 20 parts (by weight, hereafter) of an epoxy ester of dehydrated castor oil fatty acid together with a hardener to a suitable amount of toluene.
  • a solution prepared by dissolving 20/ 1000 parts of Fluorescein and 20/1000 parts of Tetrabromophenol Blue in a small amount of ethyleneglycol monomethyl ether was added in order to expand the photosensitivity of the zinc oxide to the entire range of the visible spec trum.
  • the solution was applied to an aluminium deposited polyethylene terephthalate film (thickness: 90,11.) so as to have approximately 8a of dry thickness.
  • the product when dried sufficiently in the dark place, functioned satisfactorily as the electrophotographic sensitive element.
  • This electrophotographic sensitive element was exposed to negative corona discharging in a dark place to charge uniformly the surface thereof. A color slide as the original was then loaded in an enlarger. The negatively charged sensitive element was exposed to light by projection after placing a red filter on the slide.
  • the exposed sensitive element was wetted with kerosene first and dipped quickly in the above-described liquid developer.
  • the container was a stainless steel vat, which acted as a development electrode when the surface of the element which carried the latent images was brought close to the bottom of the vat.
  • the element was removed, washed with isoparafiin (Isoper E; trade name Ml. Glacial acetic acid 40 Distilled water 60
  • the sensitive element which carried the gelatin images was soaked in this solution. The solution was agitated often. After two minutes, the zinc oxide was removed from the surface of the sensitive layer and the entire surface possessed a metallic gloss due to the aluminium layer laid under the sensitive layer.
  • the sheet was then washed sufficiently with distilled water. After soaking the sheet in acetone for 2 minutes, the sheet was placed on the bottom of the stainless steel vat which was heated by exposing the back thereof to steam at 105 C. so that the support side of the sheet contacted the bottom closely. The acetone evaporated quickly, and consequently a gelatin relief having a metallic gloss which had no drying patches was obtained.
  • the three matrices were soaked in aqueous solutions of Color Index. Acid Blue 54, Acid Violet 7 (CI. 18055) and Acid Yellow 23 (CI. 19140) for 2 minutes respectively. After removal, the sheets were washed with a washing solution containing acetic acid.
  • a sheet to be dyed having a gelatin layer was soaked in an aluminum sulfate solution. After the above described mordanting the sheet was registered to and pressed against the above-described three gelatin reliefs one after another. Through this treatment, the dyes absorbed into each of the toner images were transferred onto the gelatin layer. Thus, a duplicate having extremely high quality was obtained.
  • the fog density was 0.02. These reliefs were sufficiently durable that they could be used more than 200 times.
  • COMPARATIVE EXAMPLE Sheets washed only with water, that is, not treated with the organic solvent after the acid treatment in Example 1 were used as the relief. After soaking in the dye solutions, they were washed with an aqueous acetic acid solution and used for dye transferring. In the resulting images, the fog density was 0.28. Unevenness of the image was observed considerably.
  • EXAMPLE 2 The organic solvent treatment was carried out using methanol instead of the acetone used in Example 1, followed by drying. The resulting images were even and distinct, and had little fog.
  • EXAMPLE 3 The organic solvent treatment was carried out using ethanol instead of the acetone used in Example 1, followed by drying.
  • the maximum reflection density of the resulting images was 1.72 and the fog density was 0.05.
  • EXAMPLE 4 The organic solvent treatment was carried out using a solvent mixture of methanol and isopropyl alcohol (2:1) followed by drying. The images obtained by the dye transfer treatment were distinct similar to those of Example 1.
  • a process for forming dye images comprising forming electrostatic latent images on a sheet comprising an electrophotographic sensitive layer composed of a finelydivided photoconductive powder containing at least zinc oxide and an insulating resin on a water-resistant support and converting said latent images into gelatin images by developing with an electrophotographic developer containing a finely-divided gelatin powder, fixing said gelatin images and hardening said gelatin images on said sheet, removing said photoconductive powder from said electrophotographic sensitive layer on said sheet and washing said electrophotographic sensitive layer on said sheet with water, soaking said sheet in a water-miscible organic solvent which does not dissolve gelatin, said water-resistant support and said insulating resin, evaporating said solvent rapidly and uniformly at a temperature below the heatresistant temperature of said support to form a continuous uniform film of said insulating resin, contacting said gelatin images on said sheet with an aqueous dye solution whereby the dye is absorbed into the gelatin images, removing excess dye solution from said gelatin images on said sheet by washing
  • organic solvent is a solvent containing at least one solvent selected from the group consisting of methanol, ethanol, propyl alcohol, acetone, methyl ethyl ketone. diethylketone, methyl acetate, and ethyl acetate.
  • said finely-divided photoconductive powder contains, in addition to Zinc oxide, at least one member selected from the group consisting of CdS, CdSe, Cd(S, Se), Zn S, TiO anthracene, and polyvinylcarbazole.
  • a process for forming dye images comprising forming electrostatic latent images on a sheet comprising an electrophotographic sensitive layer composed of a finelydivided photoconductive powder containing at least zinc oxide and an insulating resin on a water-resistant support and converting said latent images into gelatin images by developing with an electrophotographic developer containing a finely-divided gelatin powder, fixing said gelatin images and hardening said gelatin images on said sheet, removing said photoconductive powder from said electrophotographic sensitive layer on said sheet and washing said electrophotographic sensitive layer on said sheet with water, removing said water, soaking said sheet in a water immiscible organic solvent which does not dissolve gelatin, said water-resistant support and said insulating resin, evaporating said solvent rapidly and uniformly at a temperature below the heat-resistant temperature of said support to form a continuous uniform film of said insulating resin, contacting said gelatin images on said sheet with an aqueous dye solution whereby the dye is absorbed into the gelatin images, removing excess dye solution from said gelatin

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US00256862A 1971-05-25 1972-05-25 Process for forming dye images Expired - Lifetime US3788845A (en)

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864125A (en) * 1969-02-10 1975-02-04 Xerox Corp Electrophotographic method of making an imaging master
US3987728A (en) * 1974-09-18 1976-10-26 Eastman Kodak Company Relief printing process
US4040828A (en) * 1975-01-06 1977-08-09 Xerox Corporation Multicolor imaging method and imaged member employing combinations of transparent toner and colorant
US4526803A (en) * 1983-06-20 1985-07-02 Baxter Travenol Laboratories, Inc. Transparentizing
US5080292A (en) * 1988-03-03 1992-01-14 Sadao Nishibori Method for pulverizing gelatin, and paint, coating layer, film and finished cloth
US5171494A (en) * 1986-08-06 1992-12-15 Ein (America) Inc. Method of producing a paint which on application imparts a surface with a tanned skin or leather-like appearance
US5225536A (en) * 1989-08-16 1993-07-06 Sadao Nishibori Particles of gelatin and amino acid to be blended in resins

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60123347U (ja) * 1984-01-30 1985-08-20 日本製罐株式会社 チユ−ブ搾り器
JPS6228748U (fr) * 1985-08-06 1987-02-21
JPS6265932U (fr) * 1985-10-11 1987-04-24
JPS6417953U (fr) * 1987-07-21 1989-01-30

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3864125A (en) * 1969-02-10 1975-02-04 Xerox Corp Electrophotographic method of making an imaging master
US3987728A (en) * 1974-09-18 1976-10-26 Eastman Kodak Company Relief printing process
US4040828A (en) * 1975-01-06 1977-08-09 Xerox Corporation Multicolor imaging method and imaged member employing combinations of transparent toner and colorant
US4526803A (en) * 1983-06-20 1985-07-02 Baxter Travenol Laboratories, Inc. Transparentizing
US5171494A (en) * 1986-08-06 1992-12-15 Ein (America) Inc. Method of producing a paint which on application imparts a surface with a tanned skin or leather-like appearance
US5080292A (en) * 1988-03-03 1992-01-14 Sadao Nishibori Method for pulverizing gelatin, and paint, coating layer, film and finished cloth
US5225536A (en) * 1989-08-16 1993-07-06 Sadao Nishibori Particles of gelatin and amino acid to be blended in resins

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GB1389333A (en) 1975-04-03

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