US3713828A - Multi-layer color photographic silver halide light-sensitive materials - Google Patents

Multi-layer color photographic silver halide light-sensitive materials Download PDF

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Publication number
US3713828A
US3713828A US00070554A US3713828DA US3713828A US 3713828 A US3713828 A US 3713828A US 00070554 A US00070554 A US 00070554A US 3713828D A US3713828D A US 3713828DA US 3713828 A US3713828 A US 3713828A
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group
layer
color photographic
silver halide
sensitive
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J Hayashi
A Sato
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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
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39292—Dyes

Definitions

  • a multi-layer type color photographic light-sensitive material characterized in that a merocyanine dye having the following general formula 1 wherein X is selected from the group consisting of a sulfur atom, a selenium atom, an oxygen atom, and
  • each of R,, R and R is selected from the group consisting of a hydrogen atom, an alkyl group a substituted alkyl group, an aryl group, and a substituted aryl group; and wherein Z represents an atomic group necessary to complete a heterocyclic ring, which may be substituted, is incorporated in at least one layer of the muIti-layer type color photographic light-sensitive material, said multi-layer type color photographic light-sensitive material having on a support at least two silver halide photographic emulsion layers is disclosed.
  • the present invention relates to a multi-layer color photographic light-sensitive material showing improved color contrast due to the interimage effect.
  • the dye formed by the reaction of the oxidation product of an aromatic primary amino color developing agent and a color former or a coupler has the property of absorbing to some extent light other than that to be absorbed. For instance, a magenta dye absorbs blue light and red light to some extent'in addition to the green light to be absorbed. Similarly, a yellow dye and cyan dye absorb to some extent light other than blue light and red light respectively. This undesirable and unnecessary absorption by the dye tends to creasing this interimage effect is not well known.
  • the reduction of the saturation of color by this unnecessary absorption of the dye may be improved-to some extent by the inter-image effect.
  • the interimage effect is a phenomenon wherein the formation of a dye image in one photographic emulsion layer influences the formation of the dye image in other photographic emulsion layers in a multi-layer color photographic light-sensitive material. With the interimage effect the color contrast can be increased.
  • the interimage effect increasing the color contrast can be explained as follows.
  • a silver halide emulsion sensitive to red light and designed to give an image of a cyan dye after development is applied to a film base and then a silver halide emulsion sensitive to blue light and designed to give an image of a yellow dye after development is further applied to the red-sensitive emulsion layer.
  • the sample thus obtained is cut into two parts. One (Sample I) of the parts is wedge exposed to red light only, while the other part (Sample II) is exposed to red light at the same exposure amount and then to blue light giving the same photographic effect as above.
  • An object of. this invention is to provide a color photographic image in which the unnecessary absorption of the dye is corrected by the interimage efiect.
  • Another object of this invention is to provide a color photographic image having a high color saturation unaccompanied with any reduction in sensitivity.
  • the inventors have found that the interimage effect occurs markedly by incorporating a merocyanine dye in at least one photographic emulsion layer of a multi-layercolor photographic light-sensitive material havingat least two silver halide photographic emulsion layers.
  • the merocyanine dye used in this invention has the general formula [I] wherein X represents a sulfuratom, aselenium atom, an oxygen atom or wherein R R and R each represents a hydrogen atom, an unsubstituted alkyl radical or an unsubstituted or substituted aryl radical; and whereinZ represents the atomic groupnecessary for forming a heterocyclic ring, which may be substituted.
  • X is a sulfur atom, a selenium atom, an oxygen atom, or
  • R R and R is a hydrogen atom; an alkyl Compound group, such as a methyl group, an ethyl group, an npropyl group, an n-butyl group, an iso-butyl group, an ass n-amyl group, and the like; a substituted alkyl group 5 I such as a Z-methoxyethyl group, a 2-hydroxyethyl group, an allyl group (or a vinylmethyl group), a benzyl group, a phenethyl group, a carboxymethyl group, a i o carboxyethyl group, a sulfomethyl group, a sulfopropyl group, a sulfobutyl group, a 4-carboxyphenethyl group,- 0 a 4-sulfophenethyl group, and the like; an aryl group such as a phenyl group; or a substituted alkyl
  • Z is an atomic group necessary to complete a heterocyclic ring.
  • the merocyanine dyes used in this invention can be readily synthesized by referring to the description in FM. Famer, The Cyanine Dyes and Related Compounds, p. 511; John Wiley & Sons Co., as well as in the specifications of US. Pat. Nos. 2,493,748 and 2,519,001.
  • the merocyanine dye of this invention can be incorporated in a multi-layer color photographic light-sensitive material by incorporating the dye in at least one of layers consisting of the silver halide emulsion layers of the color photographic light-sensitive material and the layers adjacent to the silver halide emulsion layers, such as a yellow filter layer, an antihalation layer, an intermediate layer, or a protective layer.
  • the amount of the merocyanine dye usediri this in- 7' vention depends upon the nature of the multi-layer color photographic light-sensitive material and the manner used in developing the material but where the merocyanine dye is incorporated in a silver halide emulsion layer of multilayer color photographic light- 1 sensitive material, the amount of the dye is suitably from 6 to 600 mg per mol of silver halide and where the merocyanine dye is incorporated in an emulsion layer adjacent to the silver halide emulsion layer, the amount of the dye is suitably from 6 to 600 mg per 100 g of gelatin. However, it is to be understood that variance from these amounts can be made where desired.
  • suitable solvents are those which do not adversely influence silver halide photographic emulsions, such as water, methanol, and
  • the multilayer color photographic light-sensitive material is processed at an ordinary temperature, i.e., from 20 to 30C, but the material may be processed at a higher temperature, i.e., at from 30 to C or temperatures higher than that if desired.
  • the marazyahinaa' e fihisihveiiiiofilri bamized in any of the processed providing color photographic images i.e., in any of the processes of forming dye images corresponding to the proportion of silver reduced from silver halide by developing a multi-layer color photographic light-sensitive material having at least two photographic emulsion layers, each containing a silver halide dispersion in a hydrophilic colloidal mediumJFor instance, the merocyanine dye of this invention is effectively used in a reversal color photo-' graphic process, i.e., a process for obtaining a positive color image by exposing a multi-layer color photographic light-sensitive material having at least two silver halide photographic emulsion layers, each having a sensitivity in a different wavelength region, developing the light-sensitive material in a black and white developer solution to form a negative silver image and thereafter developing the silverhalide emulsion particles at the areas which have not been developed by the black and white developing solution to form a positive color
  • Reversal color photography is classified into two systems, Le, a coupler-in-developer type color photographic system, and a coupler-in emulsion layer color photographic system.
  • Le a coupler-in-developer type color photographic system
  • coupler-in emulsion layer color photographic system the dye images are obtained by developing successively an exposed color photographic light-sensitive material in color developer solutions, each of the solutions containing a diffusible coupler to be coupled in each of the different color layers.
  • each layer contains a'diffusion resisting coupler to be coupled in each of the different color layers incorporated in a multi-layer type color photographic light-sensitive material with" the dye images being obtained by processing the light-sensitive material in a color developer solution containing no couplers.
  • the merocyanine dye of this invention can be ap plied with good results to both types of the reversal color photographic systems.
  • the merocyanine dye of the'present invention also can be used in a system in which a multi-layer type color photographic light-sensitive material, having at least two layers of a silver halide photographic emulsion, each containing a diffusion resisting coupler and each sensitized to a different wave length region, is exposed and then immediately color-developed to provide a negative colorimage.
  • the merocyanine dye of this invention can be used in a color photographic diffusion transfer process, in which the diffusion of a developing solution,
  • the merocyanine dye of this invention can be used in a silver dye bleaching color photography in which a dye image is obtained by bleaching the dye at the areas where the silver is present, as disclosed in the specifications of US. Pat. Nos. 2,020,775 and 2,410,025.
  • the multi-layer type color photographic light-sensitive material of this invention it is desirable to form the cyan, magenta and yellow images in the red-sensitive, green-sensitive, and blue-sensitive silver halide emulsion layers, respectively, after development..
  • the silver halide emulsion used in the present invention can be photographic emulsions containing silver bromide, silver iodide, silver chloride, silver chlorobromide, silver iodobromide, or silver chloroiodobromide.
  • a photographic emulsion layer containssilver chloroiodide, silver iodobromide or silver chloro-iodobromide'"having an iodine content of from 1 to mol percent, better results can be obtained.
  • the silver halide photographic emulsion used in this invention can be spectrally sensitized using a cyanine dye such as 1,1- diethylcyanine iodide, l,l -diethyl-9-methylcarbocyanine bromide, anhydro-S,5-diphenyl-9-ethyl-3,3- di(2sulfoethyl)-benzoxazolocarbocyanine hydroxide, and the like, ora combination thereof.
  • a cyanine dye such as 1,1- diethylcyanine iodide, l,l -diethyl-9-methylcarbocyanine bromide, anhydro-S,5-diphenyl-9-ethyl-3,3- di(2sulfoethyl)-benzoxazolocarbocyanine hydroxide, and the like, ora combination thereof.
  • the silver halide photographic emulsion used in this invention can contain a developing agent capable of releasing a development inhibitor such as 2-iodo-5-pentadecylhydroquinone, 2-methyl-5-( l-phenyl-5- tetrazolylthio)-hydroquinone, and the like; a stabilizer such as 4-hydroxy-6-methyl-l ,3,3a-7-tetraazaindene, benzirnidazole, 1-phenyl-5-mercaptotetrazole, and the like; a hardening agent such as formaldehyde, mucobromic acid, and the like, and a wetting agent such as saponine; sodium alkylbenzenesulfonate, and the like.
  • a developing agent capable of releasing a development inhibitor such as 2-iodo-5-pentadecylhydroquinone, 2-methyl-5-( l-phenyl-5- tetrazolylthio)-
  • COUPLER-lN-DEVELOPER TYPE COLOR PHOTOGRAPHIC SYSTEM silver content waslS mg/l 00 cm.
  • the yellow filter layer a layer formed by coating a yellow 'colloidal silver dispersion, prepared by dispersing colloidal silverin gelatin so that the silver content was 2.5 ing/ cm.
  • the blue-sensitive gelatino silver halide emulsion layer a layer formed by coating a high speed silver iodobromide emulsion containing no coupler so that the silver content was 20 mg/ 100 cm.
  • Negative Developer Solution N-Methyl'p-aminophenol Sulfate 5.0 g Sodium Sulfite 79.0 g Hydroquinone 2.0 g Sodium Hydroxide 1.0 g Sodium Carbonate (1 11,0) 41.0 0.1% Potassium Iodide lZS cc 3 Potassium Bromide V H A w 3.6 g Sodium Hydroquinone Monosulfonate 4.0 g Potassium Thiocyanate 2.0 g 0.5% 6-Nitrobenzoindazole Nitrate 5.0 cc Water added to make the total volume to 1000 cc.
  • First Layer (Lowermost Layer) The antihalation layer; a layer formed by coating a gray colloidal silver dispersion prepared by dispersing colloidal silver in gelatin so that the silver content was 3 mg/ cm Second Layer An intermediate layer; a layer formed by coating a gelatin solution so that the content of the gelatin was 3.4 mg/l00 cm Third Layer The red-sensitive silver halide emulsion layer; a layer formed by coating a high speed gelatino silver iodobromide emulsion having red sensitivity due to a sensitizing dye and containing a cyan coupler (a coupler emulsion prepared by dispersing in gelatin a solution of 1- hydroxy-4-chloro-N-dodecyl-2-naphthamide in -tricresyl phosphate) so
  • Fourth Layer An intermediate layer; a layer formed by coating a gelatin solution so that the gelatin content was 13.4 mg/lOO-cm.
  • Fifth Layer The green-sensitive gelatino silver halide emulsion layer; a layer formed by coating a high speed silver bromide emulsion having green sensitivity due to sensitizing dye and containing a magenta coupler (a coupler emulsion prepared by dispersing in gelatin a solution of l-(2,6-dichloro-4-methoxyphenyl)-3-[3- a-(2.
  • the yellow filter layer a layer, prepared by coating a yellow colloidal silver dispersion formed by dispersing colloidal silver in gelatin so that the silver content was 2.5 mg/100cm
  • the blue-sensitive silver halide emulsion layer a layer formed by coating a high speed gelatino silver iodobromide emulsion containing a yellow coupler (a coupler emulsion prepared by dispersing in gelatin a solution of 2-benzoyl-2-chloro-,5'-tridecanoyloxyacetanilide in dibutylphthalate) so that the silver content was 15 mg/lOO cm.
  • Second Developer Solution Benzyl Alcohol 5.0 cc Sodium Sulfite 5.0 g Hydroxylamine Hydrochloride 2.0 g 3-Methyl-4-arnino-N-ethyl'N-(B- methylsulfonamidoethyl)aniline Sulfate L5 g Potassium Bromide l.0 g Trisodium Phosphate 30 g Sodium Hydroxide 0.5 g Ethylenediamine (70% aqueous solution) 7 cc Water added to make'the total volume to i000 cc.
  • Bleaching Solution Ferricyanide 100 g Sodium Acetate 40 g Glacial Acetic Acid 20 g Potassium Bromide 30 g Water added to make the total volume to i000 cc.
  • EXAMPLE 1 According to theZ-above descriptions, two types of multi-layer type color photographic light-sensitive materials of the coupler-in-developer type color photographic system were prepared. One of them was used as a control sample and in another sample, Compound 1 1 shown hereinbefore, was added to the three silver halide emulsion layers (first layer, second layer and fourth layer) inthe amount of 40 mg per l mol of silver halide. I
  • Each of the multi-layer type color photographic light-sensitive materials thus prepared was subjected to the following two types of sensitometrie exposures, i.e., exposed to red light andto white light (red light green light blue light).
  • red light andto white light red light green light blue light
  • the samples thus exposed were developed using the developing procedures. After development,.the density of the cyan dye in the samples was obtained as a function of the amount of exposure of the red light. From the ratio of the gamma'valves of the characteristic'curves of the cyan dye images in the case of exposure to red light alone and in the case of exposure'to white light ('y /y where 7,. is the gamma value of the cyan dye image when exposed to red light and 7 is the gamma value when exposed to white light), the interimage effect was evaluated.
  • log E at D 0.6 of the cyan dye image when exposed to red light
  • the multi-layer type color photographic light-sensitive materialsthus obtained were subjected to exposure and development as in Example I and also the density was measured as in Example 1, whereby the ratio y l-y was obtained.
  • the multilayer type colorphotographic light-sensitive material in order to determine the influence of the compounds shown in Table 2 on the sensitivity of the blue-sensitive layer, the multilayer type colorphotographic light-sensitive material 'wassensitometrically exposed to blue light. Thereafter each of the light-sensitive materials was processed in accordance with the developing procedures of the coupler-in-developer type color photographic system and the density of the yellow dye image was measured.
  • the multi-layer type color photographic light-sensitive materials thus obtained were sensitometrically exposed to the following four different kinds of light, respectively. That is to say, each of the light-sensitive materials were exposed tored light, green light, blue 50 light, or white light (red light green light blue light) separately.
  • the amount of exposure of the red component, the green component or the blue component of the white light was the same as that of the exposure to red light, the exposure to green light, or the exposure to blue light alone and the amount of exposure to each of the red light, green light and blue light was so ad jisted that the same photographic effect was obtained.
  • the samples thus exposed were developed using the developing process of the coupler-in-emulsion type color photographic system as described hereinbefore. After development, the ratio of the gamma values 7 W of the characteristic. curves of the cyan dye images when exposed to red light and when exposed to white light, the gamma value ratio y /7 of the characteristic curves of the magenta dye images when exposed to green light and when exposed to white light, and the gamma value ratio of 7 of the characteristic curves 1 or Compound 7 the ratios 'y l'y 7 /7 and 'y l-y were greatly increased, that is to say, the interimage effects were increased.
  • a multi-layer type color photographic light-sensitive material characterized in that a merocyanine dye having the following general formula [I] wherein X is a member selected from the group consisting of a sulfur atom, a selenium atom, an oxygen atom, and a group; wherein each of R,, R, and R is a member elected from the group consisting of a hydrogen atom, an alkyl group, a substituted alkyl group, whose substituents are selected from the group consisting of an alkoxy group, a hydroxy group, a vinyl group, an aryl group, a carboxy group, and a sulfo group, an aryl group, and a substituted arylgroup, whose substituents are selected from the group consisting of a carboxy group and a sulfogroup; and wherein Z represents an an atomic group necessary to complete a heterocyclic ring selected from -the group consisting of thiazolines, thiazoles, benzthiazoles,
  • the silver halide in at least one of the aforementioned silver halide emulsion layers containing a silver iodide content of from 1 to 10.0 mole percent, and
  • the silver halide in at least one of the silver halide emulsion layers being a member selected from the group consisting of Agcll, AglBr and AgCllBr, whose concentration ranges from 1 to 10.0 mole percent, the remaining silver halide emulsion layers containing a silver halide selected from the group consisting of AgBr, Agl, AgCl, AgClBr, Ag-
  • each of R,, R and R is selected from a group consisting of a hydrogen atom, a methyl group, an ethyl group, an npropyl group, an n-butyl group, an iso-butyl group, an n-amyl group, a 2-methoxyethyl group, a Z-hydroxyethyl group, an allyl group, a benzyl group, a phenyl group, a carboxymethyl group, a carboxyethyl group, a sulfomethyl group, a sulfopropyl group, a sulfobutyl group, a 4-carboxyphenethyl group, a 4-sulfophenethyl group, a phenyl group, a 4-carboxyphenyl group, and a 4-sulfophenyl group.
  • heterocyclic ring completed by Z is selected from the group consisting of the thiazolines, thiazoles, benzthiazoles, naphthothiazoles, oxazoles, benzoxazoles, naphthoxazoles, selenazoles, benzselenazoles, naphthoselenazoles, indolenines, benzimidazoles, naphthoimidazoles, Z-quinolines and Z-pyridines.
  • the multi-layer type color photographic light-sew sitive material as claimed in claim I wherein the silver halide is selected from the group consisting of silver bromide, silver iodide, silver chloride, silver chlorobromide, silver iodobromide, and silver chloro-iodobromide.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US00070554A 1969-09-05 1970-09-08 Multi-layer color photographic silver halide light-sensitive materials Expired - Lifetime US3713828A (en)

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JP (1) JPS4834168B1 (enExample)
BE (1) BE755812A (enExample)
DE (1) DE2043943B2 (enExample)
FR (1) FR2060895A5 (enExample)
GB (1) GB1323466A (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3881936A (en) * 1970-11-25 1975-05-06 Fuji Photo Film Co Ltd Silver halide photographic emulsion containing three sensitizing dyes
US3930860A (en) * 1972-12-29 1976-01-06 Fuji Photo Film Co., Ltd. Spectrally sensitized color photographic materials suitable for high temperature rapid development
DE3243907A1 (de) * 1981-11-26 1983-06-01 Konishiroku Photo Industry Co., Ltd., Tokyo Lichtempfindliches photographisches silberhalogenid-aufzeichnungsmaterial
US4960689A (en) * 1987-06-05 1990-10-02 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material and method of developing the same
US5281515A (en) * 1991-09-18 1994-01-25 Minnesota Mining And Manufacturing Company Thermally developable photographic elements
EP1750173A1 (en) 2005-08-04 2007-02-07 Fuji Photo Film Co., Ltd. Silver halide photosensitive material and packaged body containing the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5195075U (enExample) * 1975-01-29 1976-07-30
JPS52149466U (enExample) * 1976-05-08 1977-11-12

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2504615A (en) * 1945-12-29 1950-04-18 Gen Aniline & Film Corp Photographic emulsions containing nu-aryloxy-, arylthio-, and arylselenoalkyl cyanine dyes
US2692829A (en) * 1951-02-17 1954-10-26 Eastman Kodak Co Photographic emulsions sensitized with merocyanine dyes containing a 5(4)-thiazolone nucleus
US2944901A (en) * 1957-01-18 1960-07-12 Eastman Kodak Co Multicontrast photographic emulsions
US3384486A (en) * 1964-05-04 1968-05-21 Eastman Kodak Co Merocyanine dyes for photographic elements containing an extracyclic tertiary amino group
US3480434A (en) * 1965-11-26 1969-11-25 Eastman Kodak Co Sensitizer for blue-sensitive emulsions
US3573916A (en) * 1968-04-08 1971-04-06 Eastman Kodak Co Method for preparing color elements providing mottle-free dye images

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2504615A (en) * 1945-12-29 1950-04-18 Gen Aniline & Film Corp Photographic emulsions containing nu-aryloxy-, arylthio-, and arylselenoalkyl cyanine dyes
US2692829A (en) * 1951-02-17 1954-10-26 Eastman Kodak Co Photographic emulsions sensitized with merocyanine dyes containing a 5(4)-thiazolone nucleus
US2944901A (en) * 1957-01-18 1960-07-12 Eastman Kodak Co Multicontrast photographic emulsions
US3384486A (en) * 1964-05-04 1968-05-21 Eastman Kodak Co Merocyanine dyes for photographic elements containing an extracyclic tertiary amino group
US3480434A (en) * 1965-11-26 1969-11-25 Eastman Kodak Co Sensitizer for blue-sensitive emulsions
US3573916A (en) * 1968-04-08 1971-04-06 Eastman Kodak Co Method for preparing color elements providing mottle-free dye images

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3881936A (en) * 1970-11-25 1975-05-06 Fuji Photo Film Co Ltd Silver halide photographic emulsion containing three sensitizing dyes
US3930860A (en) * 1972-12-29 1976-01-06 Fuji Photo Film Co., Ltd. Spectrally sensitized color photographic materials suitable for high temperature rapid development
DE3243907A1 (de) * 1981-11-26 1983-06-01 Konishiroku Photo Industry Co., Ltd., Tokyo Lichtempfindliches photographisches silberhalogenid-aufzeichnungsmaterial
US4517284A (en) * 1981-11-26 1985-05-14 Konishiroku Photo Ind. Co., Ltd. Light-sensitive silver halide photographic material
US4960689A (en) * 1987-06-05 1990-10-02 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material and method of developing the same
US5281515A (en) * 1991-09-18 1994-01-25 Minnesota Mining And Manufacturing Company Thermally developable photographic elements
EP1750173A1 (en) 2005-08-04 2007-02-07 Fuji Photo Film Co., Ltd. Silver halide photosensitive material and packaged body containing the same

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DE2043943A1 (de) 1971-03-18
FR2060895A5 (enExample) 1971-06-18
JPS4834168B1 (enExample) 1973-10-19
BE755812A (fr) 1971-02-15
DE2043943B2 (de) 1979-10-31
GB1323466A (en) 1973-07-18

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