EP0274723B1 - Filterfarbstoff für photographisches Element - Google Patents

Filterfarbstoff für photographisches Element Download PDF

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Publication number
EP0274723B1
EP0274723B1 EP19870118944 EP87118944A EP0274723B1 EP 0274723 B1 EP0274723 B1 EP 0274723B1 EP 19870118944 EP19870118944 EP 19870118944 EP 87118944 A EP87118944 A EP 87118944A EP 0274723 B1 EP0274723 B1 EP 0274723B1
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EP
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Prior art keywords
dye
substituted
layer
unsubstituted alkyl
taken together
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Expired - Lifetime
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EP19870118944
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English (en)
French (fr)
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EP0274723A1 (de
Inventor
Donald R. C/O Eastman Kodak Company Diehl
Ronda E. C/O Eastman Kodak Company Factor
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Eastman Kodak Co
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Eastman Kodak Co
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/16—X-ray, infrared, or ultraviolet ray processes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/74—Applying photosensitive compositions to the base; Drying processes therefor
    • G03C2001/7448—Dispersion
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C2200/00—Details
    • G03C2200/44—Details pH value
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C2200/00—Details
    • G03C2200/46—Details pKa value

Definitions

  • This invention relates to filter dyes and their use in photographic elements.
  • Filter dyes are widely used in photographic elements. Filter dyes may be located in several locations in an element. They may be in a radiation-sensitive layer, an overcoat layer, in a layer adjacent to the radiation-sensitive layer, in an interlayer of a multilayer element, in an undercoat layer adjacent to the support or in a backing layer on the side of the support opposite the radiation-sensitive layer.
  • the filter dyes When incorporated directly in the radiation-sensitive layer they can function to improve sharpness by absorbing light scattered from one silver halide grain to another. Such dyes are referred to as absorber dyes. Filter dyes also function to retard the sensitivity of one light sensitive layer relative to another in a multilayer element. By absorbing some of the exposing radiation the filter dye aids in balancing the sensitivities of all the light sensitive layers.
  • Filter dyes that function primarily to absorb unwanted radiation due to reflection or refraction from layer interfaces, the layer-support interface, and particularly from the back side of the support, are referred to as antihalation dyes.
  • the layers that contain them are referred to as antihalation layers.
  • filter layer may be used in or near the overcoat layer to protect the light sensitive layer against radiation from certain spectral regions.
  • a filter layer may be used in or near the overcoat layer to protect the light sensitive layer against radiation from certain spectral regions.
  • filter dye interlayers In multilayer films where there may be two or more light sensitive layers, it is sometimes necessary to have filter dye interlayers.
  • duplitizedo materials such as X-ray films, filter layers are used to reduce crossover exposure of the light sensitive layers. Elimination of crossover exposure is an ideal that is highly desirable but has not yet been fully attained.
  • a number of problems are associated with filter dyes and filter layers. It is very important that the dyes remain in the layer and not wander or diffuse into the adjacent layers. This often necessitates the presence of a mordant to hold the dye in the layer. It is equally important for the dyes to be completely decolorized and/or removed from the element, usually during processing, after they have performed their function. Dye stability, especially under high temperature and high humidity incubation is also important.
  • U.S. Patent 3 560 214 discloses dyes comprising a carboxyl and phenyl substituted pyrazoline nucleus linked through a methine group to a dialkyl-aminophenyl group.
  • these dyes according to the patent and our own experiments, are migratory.
  • DE-A 1 909 463 describes, as photographic filter dyes, 2-pyrazolin-5-one arylidene compounds having carboxyl substituents bonded directly to the 2-pyrazolin-5-one ring at the 3-position. These filter dyes, however, can wander from the layers in which they are coated, adversely affecting the light-sensitive silver halide layers of the photographic material.
  • DD-A 109 455 describes water-soluble carboxy salt-substituted arylidene compounds in photographic filter layers. This reference describes the use of large ballasting groups as substituents on the dye molecules in an attempt to limit wandering of these water-soluble dyes.
  • DE-A 2 262 794 describes water-soluble arylidene compounds as photographic filter dyes.
  • A represents a substituted or unsubstituted nucleus having a carboxyphenyl or sulfonamidophenyl substituent selected from the group consisting of 2-pryazolin-5-ones free of any carboxyl group substituent bonded directly thereto, rhodanines, hydantoins, 2-thiohydantoins, 4-thiohydantoins, 2,4-oxazolidindiones, 2-thio-2,4-oxazolidindiones, isoxazolinones, barbiturics, 2-thiobarbiturics, and indandiones,
  • the dyes useful in the practice of the invention are merostyryl arylidenes having the formula:
  • the carboxyphenyl substituent on A is important in immobilizing the dye at coating pH's of 5-7.
  • the acyl, alkyl and alkoxy groups may contain from one to twenty carbons. Examples of such groups include acetyl, benzoyl, methyl, ethyl, propyl, methoxy carboxyl, ethoxy carboxyl, butoxycarboxyl, fluoralkyl, dodecyl, and octadecyl.
  • the aryl groups may contain from six to twenty carbons, which may be further substituted with a wide variety of groups. Examples of such substituted and unsubstituted aryl groups including phenyl and napthyl with alkyl substituents as defined above.
  • Microcrystalline dispersions of the dyes of this invention leave no residual post-processing stain in processed photographic elements.
  • Polymeric mordants are not needed to immobilize the dyes, as immobilization is achieved without mordants.
  • Complete and irreversible dye removal during processing is achieved.
  • Broadened and shifted absorption is obtained which makes the compositions particularly suitable for filter or antihalation applications. Their broadened absorption bands are particularly useful in reducing the number of dyes needed in a single element to absorb unwanted radiation. Another advantage is superior dye stability when subjected to high temperature and high humidity incubation.
  • Examples 1-3 below relate to the preparation of representative dyes of the above formulas. Variations on the procedures described to obtain other dyes of these formulas, such as those of the examples and Table I and II below are within the skill of the practicing synthetic chemist. Procedures for making such dyes are described in "The Cyanine Dyes and Related Compounds", Frances Hamer, Interscience Publishers, 1984.
  • NMR nuclear magnetic resonance
  • IR infrared
  • HCI hydrochloric acid
  • EtOH ethanol
  • MeOH methanol
  • Et 2 0 ethyl ether
  • DMF dimethylformamide
  • DM-SO dimethylsulfoxide
  • the above dyes in Tables I and II may also have sulfonamido substituents instead of the carboxyl sub- stitutents, such as:
  • the dyes useful in the practice of this invention are useful in, for example, black and white, single color, multicolor, or duplitized®* X-ray photographic elements. They can be present in any layer of the element where it is desirable to include a filter dye, for example, in the silver halide emulsion layer or a separate filter layer.
  • the dyes useful in the practice of the invention can be utilized in any amount that is useful to filter or absorb light, but it is particularly advantageous to utilize them in an amount and in a location so that they will be solubilized and washed out during processing.
  • the dye is preferably present in the element of the invention in an amount of from 0.01 to 10.76 g/m 2 .
  • the dyes useful in the practice of the invention are in the form of a solid particle microcrystalline dispersion for incorporation into a layer such as a hydrophilic colloid layer coated on a photographic element.
  • the microcrystalline dispersion can be formed by precipitating the dye in the form of a dispersion and/or by well-known milling techniques, e.g., ball-milling, sand-milling, or colloid-milling the dye in the presence of a dispersing agent.
  • the dye particles in the dispersion preferably have a mean diameter of less than 10 Itm and more preferably of less than 1 [L m.
  • the dye particles can be conveniently prepared in sizes ranging down to 0.01 ⁇ m or less.
  • Multicolor elements contain dye image-forming units sensitive to each of the three primary regions of the spectrum.
  • Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element, including the layers of the image-forming units, can be arranged in various orders as known in the art.
  • the emulsions sensitive to each of the three primary regions of the spectrum can be disposed as a single segmented layer, e.g., as by the use of micro-vessels as described in U.S. Patent 4,362,806.
  • a typical multicolor photographic element would comprise a support bearing a cyan dye image-forming unit comprised of at least one red-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, a magenta dye image-forming unit comprising at least one green- sensitive silver halide emulsion layer having associated therewith at least one magenta dye-forming coupler and a yellow dye image-forming unit comprising at least one blue-sensitive silver halide emulsion layer having associated therewith at least one yellow dye-forming coupler.
  • the element can contain additional layers, other filter layers, interlayers, overcoat layers, subbing layers, and the like.
  • the silver halide emulsions employed can be either negative-working or positive-working. Suitable emulsions and their preparation are described in Research Disclosure Sections I and II and the published cations cited therein. Suitable vehicles for the emulsion layers and other layers are described in Research Disclosure Section IX and the publications cited therein.
  • the elements can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein. These couplers can be incorporated in the elements and emulsions as described in Research Disclosure Section VII, paragraph C and the publications cited therein.
  • the photographic elements or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilizers (see Research Disclosure Section VI), antistain agents and image dye stabilizer (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XI), plasticizers and lubricants (see Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
  • the photographic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
  • Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX.
  • Processing to form a visible dye image includes the step of contacting the element with a color developing agent to reduce developable silver halide and oxidize the color developing agent. Oxidized color developing agent in turn reacts with the coupler to yield a dye.
  • the dyes were subjected to ball-milling according to the following procedure. Water (21.7 ml) and a 6.7% solution of Triton X-200 @ surfactant (TX-200 @ ) (2.65 g) (available from Rohm & Haas) were placed in a 60 ml screw-capped bottle. A 1.00 g sample of dye was added to this solution. Zirconium oxide (ZrO) beads (40 ml) (2 mm diameter) were added and the container with the cap tightly secured was placed in a mill and the contents were milled for four days. The container was removed and the contents added to a 12.5% aqueous gelatin (8.0 g). The new mixture was placed on a roller mill for 10 minutes to reduce foaming and the resulting mixture was then filtered to remove the ZrO beads.
  • ZrO Zirconium oxide
  • a spreading agent, surfactant 10G @ , and a hardener bis(vinyl-sulfonylmethyl)ether
  • a melt prepared from the latter mixture was then coated on polyethylene terephthalate support to achieve a dye coverage of 0.32 g/m 2 , gelatin coverage of 1.60 g/m 2 , a spreading agent level of 0.096 g/m 2 and a hardener level of 0.016 g/m 2 .
  • Spectral data were obtained from an analysis of the coatings on a spectrophotometer interfaced with a computer. A summary of the data obtained is in Table III where the dye numbers correspond to those of Tables I and II.
  • HBW half band width
  • microcrystalline dispersions of dyes according to the invention are suitable for filter applications where broad visible light filtration is required. This broad absorption also serves to reduce the number of dyes needed for a particular filter application.
  • the coated microcrystalline dye dispersions prepared as described in the previous examples were evaluated for dye mobility. Samples of the coatings were given a five minute distilled water wash. The results for four of the dyes, 1, 2, 3 and 5, are shown in Table IV. The coatings were also evaluated for post processing stain following processing in the Kodak Prostaro processor used commercially to process microfilm, subjecting the elements to a development step at a pH of 11.4 for 30 seconds. These results are also included in Table IV.
  • Table IV shows that no dye density was lost by the dyes dispersed and coated as described in the previous examples due to the distilled water wash. This shows that there was no dye wandering from layer to layer.
  • the comparison dye on the other hand, exhibited severe washout, indicating a high degree of dye wandering.
  • Table IV also demonstrates dramatically the complete removal of the microcrystalline dispersion dyes on Prostar@ processing at room temperature. No residual stain is left. The same results were observed when the coatings were processed with Kodak X-Omat@ processing, which is used commercially to process x-ray film, subjecting the elements to a development step at a pH of 10.3 for 30 seconds. This is an improvement over other known latex imbibed yellow filter dyes which are incompletely removed by these processing conditions.
  • Dye 25 had a ⁇ -max of 449 nm and a bandwidth of 121 nm before washing or processing.
  • Dye 26 had a ⁇ ,-max of 453 nm and a bandwidth of 97 nm before washing or processing.
  • Table V indicate that the photographic compositions of the invention containing Dyes 25 and 26 do not wander during the water wash, but decolorize completely after photographic processing.
  • microcrystalline dispersions of dyes according to the invention in combination with other dyes, is illustrated with dyes 1 and 5 of Table I.
  • the dispersions were prepared as in examples 5-19. These dispersions were each coated as a component of an antihalation layer in a multilayer format, along with a cyan filter dye, bis[1-(4-carboxyphenyl)-3-methyl-2-pyrazolin-5-one-(4)]pentamethineoxonol.
  • the coatings, 1 to 4 in Table VI were evaluated for dye stain after processing.
  • the emulsion layer was a chemically and spectrally sensitized 0.25 micron cubic silver bromoiodide (3% iodide) emulsion layer coated to achieve silver coverage of 1.45 g/m2 and gelatin coverage of 1.56 g/m 2.
  • the gelatin coverage in the antihalation layer was 1.88 g/m 2 .
  • the levels of dyes 1 and 5 and of the cyan dye are indicated in Table VI.
  • the gelatin coverage in the overcoat layer was 1.56 g/m 2 .
  • the coatings were exposed to a tungsten light source in a sensitometer, developed, fixed and washed in the Kodak Prostar@ process and dried.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (7)

1. Photographisches Element mit einem Träger und einer strahlungsempfindlichen Silberhalogenidschicht, gekennzeichnet durch eine Schicht mit einer Dispersion von mikrokristallinen Feststoffteilchen eines Farbstoffes der Formel:
Figure imgb0020
worin bedeuten
A einen substituierten oder unsubstituierten sauren Kern mit einem Carboxyphenyl- oder Sulfonamidophenyl-Substituenten, ausgewählt aus der Gruppe bestehend aus 2-Pyrazolin-5-onen, frei von Carboxylgruppensubstituenten, die direkt an diese gebunden sind, Rhodaninen, Hydantoinen, 2-Thiohydantoinen, 4-Thiohydantoinen, 2,4-Oxazolidindionen, 2-Thio-2,4-oxazolidindionen, lsoxazolinonen, Barbitursäuren, 2-Thiobarbitursäuren und Indandionen,
R Wasserstoff, substituiertes oder unsubstituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen oder Benzyl,
R1 und R2 jeweils unabhängig voneinander substituiertes oder unsubstituiertes Alkyl oder Aryl oder gemeinsam mit R5, R6, N und den Kohlenstoffatomen, an die sie gebunden sind, die Atome, die zur Vervollstandigung eines Julolydylringes erforderlich sind,
R3 Wasserstoff oder substituiertes oder unsubstituiertes Alkyl oder Aryl,
R5 und R6 jeweils unabhängig voneinander Wasserstoff, oder R5 gemeinsam mit Rl, oder R6 gemeinsam mit R2 jeweils die Atome, die zur Vervollständigung eines carbocyclischen Ringes erforderlich sind, und m gleich 0 oder 1.
2. Photographisches Element nach Anspruch 1, in dem die Schicht auf der Seite des Trägers angeordnet ist, die der Silberhalogenidschicht gegenüberliegt.
3. Photographisches Element nach Anspruch 1, in dem sich die Silberhalogenidschicht auf einer Seite des Trägers befindet und bei dem sich eine zweite strahlungsempfindliche Silberhalogenidschicht auf der anderen Seite des Trägers befindet und in dem die Farbstoffschicht zwischen einer der Silberhalogeniodschichten und dem Träger angeordnet ist.
4. Photographisches Element mit einem Träger und einer Schicht mit strahlungsempfindlichem Silberhalogenid, in dem die Schicht dadurch gekennzeichnet ist, daß sie einen Farbstoff der folgenden Formel enthalt:
Figure imgb0021
worin bedeuten:
A einen substituierten oder unsubstituierten sauren Kern mit einem Carboxyphenyl- oder Sulfonamidophenyl Substituenten, ausgewählt aus der Gruppe bestehend aus 2-Pyrazolin-5-onen, frei von Carboxylgruppensubstituenten, die direkt an diese gebunden sind, Rhodaninen, Hydantoinen, 2-Thiohydantoinen, 4-Thiohydantoinen, 2,4-Oxazolidindionen, 2-Thio-2,4-oxazolidindionen, Isoxazolinonen, Barbitursäuren, 2-Thiobarbitursäuren und Indandionen,
R Wasserstoff, substituiertes oder unsubstituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen oder Benzyl,
R1 und R2 jeweils unabhängig voneinander substituiertes oder unsubstituiertes Alkyl oder Aryl oder gemeinsam mit R5, R6, N und den Kohlenstoffatomen, an die sie gebunden sind, die Atome, die zur Vervollständigung eines Julolydylringes erforderlich sind,
R3 Wasserstoff oder substituiertes oder unsubstituiertes Alkyl oder Aryl,
R5 und R6 jeweils unabhängig voneinander Wasserstoff, oder R5 gemeinsam mit Ri, oder R6 gemeinsam mit R2 jeweils die Atome, die zur Vervollständigung eines carbocyclischen Ringes erforderlich sind, und m gleich 0 oder 1.
5. Photographisches Element nach Ansprüche 1 bis 4, in dem der Farbstoff ein Merostyrylaryliden-Farbstoff der folgenden Formel ist:
Figure imgb0022
worin bedeuten:
R Wasserstoff, substituiertes oder unsubstituiertes Alkyl mit 1 bis 4 Kohlenstoffatomen oder Benzyl,
R1 und R2 jeweils unabhängig voneinander substituiertes oder unsubstituiertes Alkyl oder Aryl, oder gemeinsam mit R5, R6, N, und den Kohlenstoffatomen, an die sie gebunden sind, die Atome, die zur Vervollständigung eines Julolydylringes erforderich sind,
R3 und R7 jeweils unabhängig voneinander Wasserstoff, substituiertes oder unsubstituiertes Alkyl, Aryl, Alkoxy oder Acetamido,
R4 substituiertes oder unsubstituiertes Alkyl, Alkoxycarbonyl, Aryl, Acyl oder Amido,
R5 und R6 jeweils unabhängig voneinander Wasserstoff, oder R5 gemeinsam mit Rl, oder R6 gemeinsam mit R2 die Atome, die zur Vervollständigung eines carbocyclischen Ringes erforderlich sind,
RB gleich CO2H oder NHS02R9, worin R9 für substituiertes oder unsubstituiertes Alkyl oder Aryl steht, x gleich 1 oder 2 und
n gleich 0 oder 1.
6. Photographisches Element nach Anspruch 5, worin bedeuten: R1 und R2 jeweils unabhnägig voneinander
Figure imgb0023
oder
Figure imgb0024
R3 gleich H, CH3 oder OH,
R4 gleich CH3 oder COOC2H5,
R5, R6 und R7 jeweils H, oder R5, R6, R1 und R2, gemeinsam mit den Atomen, an denen sie sitzen, einen Julolydylring.
7. Photographisches Element nach Ansprüchen 1 bis 6, in dem die Schicht mit dem Farbstoff eine Mischung aus Bis[1-(4-carboxyphenyl)-3-methyl-2-pyrazolin-5-on-(4)] pentamethinoxonol und einem der folgenden Farbstoffe enthält:
Figure imgb0025
und
Figure imgb0026
EP19870118944 1986-12-23 1987-12-21 Filterfarbstoff für photographisches Element Expired - Lifetime EP0274723B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US94563486A 1986-12-23 1986-12-23
US945634 1986-12-23
US10446887A 1987-10-05 1987-10-05
US104468 1987-10-05

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EP0274723A1 EP0274723A1 (de) 1988-07-20
EP0274723B1 true EP0274723B1 (de) 1990-10-31

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JP (1) JP2578146B2 (de)
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DE (1) DE3765921D1 (de)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
US6045986A (en) * 1997-05-20 2000-04-04 Tulalip Consultoria Commerial Sociedade Unipessoal S.A. Formation and photographic use of solid particle dye dispersions

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JPH02264936A (ja) * 1989-04-06 1990-10-29 Fuji Photo Film Co Ltd Ｘ線用ハロゲン化銀写真感光材料
DE69029676T2 (de) * 1989-04-06 1997-05-07 Fuji Photo Film Co Ltd Photographisches Silberhalogenidmaterial und Verarbeitungsmethode dafür
JPH0339954A (ja) * 1989-04-17 1991-02-20 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
JPH02278257A (ja) * 1989-04-20 1990-11-14 Fuji Photo Film Co Ltd 直接ポジカラー写真感光材料
JP2922528B2 (ja) * 1989-05-24 1999-07-26 富士写真フイルム株式会社 カラー画像形成法
JPH02309350A (ja) * 1989-05-25 1990-12-25 Fuji Photo Film Co Ltd ハロゲン化銀カラー反転写真感光材料
DE69024409T2 (de) * 1989-06-05 1996-11-07 Fuji Photo Film Co Ltd Photographisches Röntgenmaterial
JP2632727B2 (ja) * 1989-06-12 1997-07-23 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
JP2613804B2 (ja) * 1989-06-21 1997-05-28 富士写真フイルム株式会社 カラー画像形成方法
EP0412379B1 (de) * 1989-08-11 1996-05-15 Fuji Photo Film Co., Ltd. Silberhalogenid enthaltende, photographische, lichtempfindliche Farbmaterialien
JPH0372340A (ja) * 1989-08-11 1991-03-27 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH03100541A (ja) * 1989-09-13 1991-04-25 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JP2579220B2 (ja) * 1989-10-03 1997-02-05 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
JPH03126938A (ja) * 1989-10-12 1991-05-30 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
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JPH03127059A (ja) * 1989-10-13 1991-05-30 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料の処理方法
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DE3765921D1 (en) 1990-12-06
EP0274723A1 (de) 1988-07-20
JPS63197943A (ja) 1988-08-16
JP2578146B2 (ja) 1997-02-05
CA1286139C (en) 1991-07-16

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