US3900322A - Diffusion transfer color photographic material having developement inhibitor precursor - Google Patents

Diffusion transfer color photographic material having developement inhibitor precursor Download PDF

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US3900322A
US3900322A US296698A US29669872A US3900322A US 3900322 A US3900322 A US 3900322A US 296698 A US296698 A US 296698A US 29669872 A US29669872 A US 29669872A US 3900322 A US3900322 A US 3900322A
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diffusion transfer
photographic material
color photographic
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Yasushi Oishi
Jun Hayashi
Yoshinobu Yoshida
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/28—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/16—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/70—Sulfur atoms
    • C07D277/72—2-Mercaptobenzothiazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
    • C07D293/02—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms not condensed with other rings
    • C07D293/04—Five-membered rings
    • C07D293/06—Selenazoles; Hydrogenated selenazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
    • C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D293/12—Selenazoles; Hydrogenated selenazoles
    • 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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02—Photosensitive materials characterised by the image-forming section

Definitions

  • a diffusion transfer color photographic material having improved color separating power and giving trans ferred color images having improved density compris' ing a support having thereon at least two layers each containing a dye developer and at least two silver halide photographic emulsion layers, at least one of which contains a compound represented by general formula wherein Q represents an atomic group necessary for forming an unsubstituted or substituted heterocyclic ring and R represents an unsubstituted or substituted alkyl group. an unsubstituted or substituted aryl group, or a heterocyclic group.
  • the present invention is generally directed to diffusion transfer color photography and more particularly to a diffusion transfer color photographic material having multilayers containing dye developers capable of providing transferred color positive images by development.
  • the unreacted and unoxidized dye developers are mobile in a processing composition and at least a part of the imagewise-distributed dye developers is transferred to an image-receiving layer positioned in superposed relationship with the photosensitive emulsion to form positive dye images thereon.
  • a lightscnsitive material having a silver halide emulsion layer and a layer of dye developer is exposed and treated with a liquid processing composition in the dark by, for example, immersion, coating, spraying, etc.
  • the exposed light-sensitive material is brought into superposed relationship with an image receiving layer capable of mordanting the dye before, during, or after the application of the liquid processing composition.
  • the light-sensitive material contains a dye developer in a layer disposed behind the silver halide emulsion layer with respect to the incident direction of light, and a liquid processing composition is supplied between the light-sensitive ma terial and the image receiving sheet by spreading processing composition therebetween in a thin layer as the emulsion layer of the light-sensitive material is brought into a superposed relationship with the image-receiving layer of the image receiving sheet.
  • the liquid processing composition thus supplied diffuses into the emulsion layer causing the development of the developable silver halide in the emulsion layer.
  • the dye developer to be combined with the silver halide emulsion is immobilized in the developed areas as a result of development and the immobi lization is apparently due, at least in part, to a decrease in the mobility and solubility of the oxidation product of the dye developer as compared to the unoxidized dye developer.
  • the immobilization is considered to be also due, in part, to a local decrease in alkali density as a function of development.
  • the imagewise distribution of the mobile unoxidized dye developer is formed as a function of the exposure and development of the silver halide emulsion.
  • the imagewise distribution of the diffusible unoxidized dye developer is, at least in part, transferred to the image-receiving layer positioned in superposed relationship with the light sensitive material by imbibition. This transfer is clearly distinguished from the lessdiffusible oxidation type dye developer and forms a visible transfer image on the image-receiving layer.
  • the unoxidized dye developer which diffuses into the superposed image-receiving layer from the inside emulsion layer must pass through at least one other outside silver halide emulsion layer, and when the unoxidized dye developer diffused from the inside emulsion layer reaches the outside emulsion layer containing the developable silver halide it reacts with the developable silver halide grains in the outside emulsion layer and then is immobilized therein.
  • a mul tilayer-type lightsensitive material composed of a support having thereon a red-sensitive emulsion layer, a greensensitive emulsion layer and a blue-sensitive emulsion layer, in that order.
  • These silver halide emulsion layers have a cyan dye developer, a magenta dye developer, and a yellow dye developer, respectively, in layers disposed behind the silver halide emulsion layers or in the silver halide emulsion layers themselves.
  • the unoxidized cyan developer will diffuse by development and will pass through the green-sensitive emulsion layer before it reaches a superposed image-received layer.
  • the magenta dye developer has substantially finished the development of the developable greensensitive silver halide before the unoxidized cyan dye developer reaches the green-sensitive emulsion layer, no trouble will occur.
  • the cyan dye developer diffuses into the green-sensitive silver halide emulsion layer while developable silver halide which has not yet been developed is present in the emulsion layer, the cyan dye developer causes a reaction with the diffusible silver halide having a different color sensitivity without discriminating as to portions of such silver halide to be immobilized.
  • the unoxidized yellow dye developer will reach the green sensitive emulsion layer by diffusion. If a developable silver halide is present in the green-sensitive emulsion layer, the yellow dye developer will also be immobilized in the greensensitive emulsion layer as in the case of the cyan dye developer. Therefore, the transfer image obtained on the image-receiving layer will show a cyan density and yellow density somewhat lower than those actually due to the exposure.
  • a phenomenon as mentioned above appears when a multilayer type negative photographic material is developed, and it is called the entangled phenomenon" in this specification.
  • the reduction in transfer density and color separation due to the engangled phenomenon of the dye developers can be improved to some extent by using a superposed effect as defined below.
  • the superposed effect is based on the phenomenon that in the development of a multilayer photographic material for diffusion transfer color photography, the development of one photosensitive emulsion layer by a dye developer has an influence on the development of the other photosensitive emulsion layer or layers by a developer or developers, and further the density of a dye developer transferred to an image-receiving layer has substantially no relationship to the development in other emulsion layer or layers.
  • a film support was coated with a cyan dye developer, a red-sensitive emulsion, a magenta dye developer, and a green-sensitive emulsion, in that order.
  • the sample thus prepared was cut into two segments, one of which (sample I) was exposed uniformly to only green light with a middle intensity, while the other (sample H) was exposed uniformly to green light with a middle intensity as for sample l and then subjected to a wedge exposure by red light. After development, the density of the magenta dye transferred to the image-receiving layers was measured for samples l and ll.
  • Sample i showed the same magenta transfer density throughout all portions of the sample, while sample ll gave a transfer image having reduced magenta transfer density in proportion to the exposure amount of red light. This was clearly based on the occurence of the entangled phenomenon.
  • the superposed effect is the effect of preventing the reduction in ma genta transfer density and the phenomenon that the magenta transfer density becomes constant regardless of the amount of red light exposure. Accordingly, it may be concluded that if the superposed effect is too high, density increases.
  • Q represents an atomic group necessary for forming a heterocyclic ring which may be substituted
  • R represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or a heterocyclic ring.
  • a developing inhibitor in an emulsion layer in which development is started, a developing inhibitor accumulates around the emulsion to inhibit the occurence of development during subsequent periods. Accordingly, when a dye developer which is not combined with said emulsion layer diffuses into said emulsion layer at development, the emulsion layer is essentially in such a state that the development thereof is stopped or inhibited. Furthermore, the development inhibitor diffuses imagewise into the adjacent emulsion layer and also inhibits the development of said emulsion. Therefore, unoxidized dye developer combined with the adjacent emulsion layer is released to too great of a degree, and thus a dye developer immobilized by the entangled phenomenon will be compensated for by the aforesaid dye developer in amount.
  • An object of the invention is to provide a new photographic material for use in a diffusion transfer process.
  • Another object of this invention is to provide a color photographic material providing a transfer image having improved density by a diffusion transfer process.
  • Still another object of this invention is to provide a processfor improving the color separation of multi color transfer images and for increasing the color reproducing power of transfer images formed by a diffusion transfer process.
  • BRlEF DESCRlPTlON OF THE DRAWlNGS H05. 1 and 2 are plots of relative exposure vs optical density for certain compounds of the present invention as compared to certain prior art compounds.
  • the compounds of general formula I used in the present invention are essentially colorless compounds and insoluble in water, They are also insoluble but diffusible in an aqueous alkali.
  • Q is an atomic group necessary for forming a heterocyclic ring which may be substituted, as mentioned above.
  • heterocyclic rings and substituted heterocyclic rings are a thiazolidine-2-thion ring (such as a thiazolidine-Z-thion ring, a 4-methylthiazolidine-2-thion ring, etc.), an imidazolidine-Z-thion ring (such as a 1,3-dimethylimidazolidine-Z-thion ring, a 1,3-diethylimidazolidine-2-thion ring, etc.), a selenazolidine-2thion ring (such as a selenazolidine-Z-thion ring, a 4-methylselenazolidine-Z-thion ring, etc.), a 1,3,4-thiadiazoline- Z-thion ring (such as a l,3,4-thiadiazoline-2-thion ring, a S-methyl-methyl-
  • R in the general formula is an alkyl group, preferably having l-6 carbon atoms, or such an alkyl group substituted by, e.g., a hydroxyl group, an aryl group, a morpholino group, etc, e.g., such as a methyl group, an ethyl group, a propyl group, a hexyl group, a decyl group, a hydroxyethyl group, a benzyl group, a morpholinoethyl group, etc; an aryl group or an aryl group substituted by, e.g., an alkyl group, an alkoxyl group,
  • a halogen atom e.g., such as an phenyl group, a Z-methylphenyl group, a 4-methoxyphenyl group, a 4- chlorophenyl group, etc; or a heterocyclic group such as a 2-pyridyl, tetrazolyl, thiazolyl and triazolyl group.
  • a and B each represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an alkoxycarbonyl group, or the atomic groups necessary to form, together, a saturated or unsaturated ring having 5-6 carbon atoms, which may have been substituted, such as cyclohexadiene, benzene and cyclopentadiene; and R and R have the same meaning as R in general formula I.
  • a and B in the general formula Ila each represents a hydrogen atom; an alkyl group having 1-6 carbon atoms or such as alkyl group substituted by a hydroxyl group, a halogen atom, etc., e.g., such as a methyl group, an ethyl group, a butyl group, a hydroxyethyl group, and a 2-chloroethyl group; an aryl group or an aryl group substituted by, e.g., an alkyl group, a hydroxyl group, a halogen atom, etc., e.g., such as alkoxyl phenyl group, a 4-methylphenyl group, a 4- hydroxyphenyl group, a 3-chlorophenyl group, etc; an alkoxycarbonyl group such as.
  • a propanoyloxy group etc.
  • the groups necessary for forming, together, an un saturated ring having 5-6 carbon atoms such as a trimethylene group to form a pentacyclic ring, a tetramethylene group to form a hexacyclic ring, etc.
  • Cornpou'fl (33) 1 21 The compounds illustrated above may be prepared by well known processes. For instance, processes of producing the above compounds are described in the specifications of Japanese patent application Nos.
  • bromide or silver chloroiodo-bromide, containing 1-10 mole percent of iodine.
  • the silver halide photographic emulsion used in this invention may also have been chemically sensitized by any method well known in the art, such as by adding a compound having unstable sulfur, e.g., sodium thiosulfate, allylthiocarbazide, etc.; a gold compound, e.g., a gold complex salt of thiocyarnic acid as disclosed in U.S. Pat. Nos. 2,526,632, 2,503,776, 2,493,748 and 3,384,486; a reducing agent, e.g., stannous chloride; at polyalkyleneoxide derivative; or a combination thereof.
  • a compound having unstable sulfur e.g., sodium thiosulfate, allylthiocarbazide, etc.
  • a gold compound e.g., a gold complex salt of thiocyarnic acid as disclosed in U.S. Pat. Nos. 2,526,632, 2,503,776, 2,493,748 and 3,38
  • the silver halide emulsion used in this invention may have been sensitized by cyanine dyes such as 1,1 -diethylcyanine iodide, 1,1-diethyl-9- methylcarbocyanine bromide, anhydro-5,5-diphenyl- 9-ethyl-3 ,3 '-di( 2-sulfoethyl -benzoxazolocarbocyanine hydroxide, etc., individually or as combinations thereof.
  • cyanine dyes such as 1,1 -diethylcyanine iodide, 1,1-diethyl-9- methylcarbocyanine bromide, anhydro-5,5-diphenyl- 9-ethyl-3 ,3 '-di( 2-sulfoethyl -benzoxazolocarbocyanine hydroxide, etc., individually or as combinations thereof.
  • Representative dye developers effectively used in the Compounds 9-17 can be prepared by the process depresent invention are described in the specifications of scribed in the Journal of the Chemical Society; pages l5031509( 1949), i.e., by the reaction of a dithiocarbamate and a compound containing a halogen.
  • the compound represented by general formula l is added to a silver halide emulsion layer of the multilayer diffusion transfer color photographic material.
  • the compound may also be incorporated into a layer adjacent a photosensitive emulsion layer whereby the compound may act on the emulsion grains at the surface side of the emulsion layer utilizing the diffusion of the compound, but in such a case the effect of the compound is less. This is because while the compound may diffuse in a wet layer,
  • the compound of this invention is suitably incorporated into a silver halide emulsion in an amount of from 0.006 to 1.5 g, preferably from 0.1 to 0.01 g, per mole of silver halide therein but the amount of the compound is not necessarily limited to above values. How ever, much lesser amounts generally will not produce the desired effect and greater amounts may inhibit the development of the emulsion layer to which the compound has been added.
  • a solvent is preferably used to add the compound to the silver halide emulsion, and solvents having no harmful influence on the silver halide emulsion, such as water, methanol, and ethanol, should be used.
  • a yellow filter layer an antihalation layer
  • intermediate layers, and a protective layer may also be formed.
  • silver halide emulsion used in this invention there are photographic emulsions containing silver halides such as silver bromide, silver iodide, silver chloride, silver chlorobromidc, silver iodobromide, and silver chloroiodo-bromide. but particularly superior results are obtained when at least one photographic emulsion layer contains silver chloroiodide, silver iodo- U.S. Pat. Nos.
  • dye developers in this invention are not limited to those compounds.
  • the dye developer be dissolved in a high boiling solvent, the resulting solution be finely dispersed by emulsification in a gelatin solution, and the resulting dispersion be applied as a layer of photographic material.
  • an organic solvent substantially immiscible with water having a boiling point above 175C. is used alone or together with a solvent aid.
  • Typical examples of high boiling solvents suitably used for this purpose are described in the specification of U.S. Pat. No. 2,322,027.
  • a compound called a subsidiary developer may also be used, if desired.
  • suitable subsidiary developers there are benzenoid-type silver halide developing agents, i.e., silver halide developing agents each having a benzene or naphthalene nucleus substituted by at least two of the following groups; hydroxyl groups, amino groups and/or alkylamino groups, which can form a quinoid oxidation product by developing a A silver halide. Examples of such are hydroxyphenylhydroquinone. phenylhydroquinone, and 4'methylphenylhydroquinone.
  • Examples of other preferred subsidiary developers are the 3-pyrazolidones, preferably l-phenyl-3-pyrazolidone or l-phenyl-4,4-dimethyl3 pyrazolidone.
  • Other subsidiary developers which may be used in this invention include catechol compounds as disclosed in British Pat. No. 1,243,539, hydroquinone compounds as disclosed in U.S. Pat. No 3,253,915 and 3-pyrazo1idones as disclosed in U.S. Pat. Nos. 3,351,465 and 3,039,869, etc.
  • the subsidiary developer in this invention is not limited to those recited, however.
  • the subsidiary developer is preferably incorporated in at least one layer of a negative photographic mate rial, such as a protective layer, a silver halide emulsion layer, a dye developer-containing layer, or an intermediate layer.
  • a negative photographic mate rial such as a protective layer, a silver halide emulsion layer, a dye developer-containing layer, or an intermediate layer.
  • the subsidiary developer may be used by the method described in Japanese Pat. publication Nos. 17,383/1960 and 393/1964 in which addi tional practical examples of subsidiary developers are described.
  • the negative color photographic material of this invention may contain a stabilizer such as 4- hydroxy-6-methyl-1 ,3,3a,7-tetraazaindenc, benzimidazole, benzotriazole, and l-phenyl-S- mercaptotetrazole; a hardening agent such as formaldehyde, mucobromic acid, and dichlorotriazine; and a wetting agent such as saponin, and sodium alkylbenzene sulfonate.
  • a stabilizer such as 4- hydroxy-6-methyl-1 ,3,3a,7-tetraazaindenc, benzimidazole, benzotriazole, and l-phenyl-S- mercaptotetrazole
  • a hardening agent such as formaldehyde, mucobromic acid, and dichlorotriazine
  • a wetting agent such as saponin, and sodium alkylbenzene sulfonate.
  • the image-receiving sheet for receiving the dye developers from the negative color photographic material described above can be selected in a wide range of materials.
  • a mordant material suitably used in the image-receiving layer of the image-receiving sheet there are illustrated gelatin, polyvinyl pyrrolidone, poly-4- vinyl-pyridine, polyvinyl acetate, polyvinyl alcohol, cel lulose acetate, polyvinyl salicyloyl, partially hydrolyzed polyvinyl acetate, methyl cellulose, and mixtures thereof.
  • the support used for the image-receiving sheet may also be selected from the wide range of supports as are now used for negative color photographic materials, e.g., cellulose nitrate films, cellulose acetate films, polyvinyl acetal films, polystyrene films, polyethylene terephthalate films, polyethylene films, polypropylene films, papers, polyethylene-coated papers, and glass sheets.
  • a negative photographic material having a coated multilayer structure may be used as the support for the image-receiving sheet.
  • the support may be opaque or transparent, according to the desired use.
  • an acid polymer or a derivative of an acid compound which is capable of releasing an acid material at a definite rate is particularly useful.
  • the layer containing the material is disposed under the image-receiving layer for the dye developers.
  • Such an acid material contributes to neutralize alkali in the liquid processing composition on the imagereceiving layer.
  • a spacer layer may be inserted between the image-receiving layer and the layer containing the material capable of releasing an acid which spacer layer controls the release of the acid material.
  • the image-receiving sheet may contain a development inhibitor such as a mercaptotetrazole and iodine.
  • the liquid processing composition for developing the exposed areas of the negative photographic material is a strong alkaline solution having, generally, a pH of higher than 12 or containing more than 0.0] normal of hydroxide ions.
  • an alkali metal hydroxide such as potassium hydroxide, sodium hydroxide, etc., or sodium carbonate is usually used.
  • a viscosityincreasing compound in the case of applying the liquid processing composition as a thin uniform layer to the emulsion layer by spreading, it is preferable to incorporate in the aforesaid alkaline processing composition a viscosityincreasing compound, thereby providing a film-forming material capable of forming a comparatively solid and stable film when the processing composition is spread and dried.
  • the preferred film-forming materials are inactive to the alkaline solution.
  • filmforming materials include water-soluble polymers such as hydroxyethyl cellulose and carboxymethyl cellulose.
  • Other film-forming materials whose function of increasing the viscosity is not substantially influenced when the material is placed in an alkaline solution for a long period of time may be also used. Suitable examples of alkaline processing compositions are described in the examples.
  • the diffusion transfer color photographic material of this invention be subjected to development processing in the presence of a diffusible onium compound.
  • a diffusible onium compound there are quaternary ammonium compounds, quaternary phosphate compounds and quaternary sulfonium compounds.
  • onium compounds are l-benzyl-2-picolinium bromide, l-( 3-brornopropyl )-2-picoliniump-toluenesulfonic acid, l-phenethyl-2-picolinium bromide, 2,4- dimethyl-1-phenethylpyridinium bromide, a-picoline-B-naphthoylmethyl bromide, N,N- diethylpiperidinium bromide, phenethyltrimethyl phosphonium bromide, and dodecyldimethylsulfonium-ptoluene sulfonium. It is preferred that the onium compound be contained in the alkaline processing composition. The most preferred amount of the onium compound is 2-15 percent by weight, based on the total amount of the processing composition.
  • a development inhibitor such as benzotriazole may be incorporated in the liquid processing composition.
  • the subsidiary developer described above may also be incorporated in the liquid processing composition. At least a part of the dye developers oxidized during development are oxidized and immobilized as a result of reaction with the oxidation product of the subsidiary developer.
  • the subsidiary developer is oxidized by the development of the exposed silver halide and it is believed that the reaction of the oxidized subsidiary developer and the unoxidized dye developers regenerates the subsidiary developer to cause additional reac' tion with the exposed silver halide.
  • the aforementioned compound of this invention represented by general formula 1 has the property that when it is incorporated in an emulsion layer of a diffusion transfer color photographic material it is released imagewise with the progress of development of the photographic material.
  • the compound of this invention may be said to be a compound having a development inhibiting action but the behavior thereof differs completcly from the case when a conventional developing inhibitor well known in the field of photography is incorporated in light-sensitive materials. That is to say, when such a conventional development inhibitor is employed, the above-mentioned superposed effect is not obtained and the overall sensitivity of the lightsensitive material containing it is reduced, while when the compound of this invention is employed, almost no reduction in sensitivity of light-sensitive material occurs and further a remarkable superposed effect is obtained.
  • the compound of this invention exhibits its effect when it is incorporated not only in a photographic emulsion layer of a multilayer color photographic material of the type wherein the dye developer is incorporated in the light-sensitive layer adjacent to the photographic emulsion layer but also in a multilayer color photographic material of the type wherein the dye developer is incorporated in the photographic emulsion layer.
  • a multilayer diffusion transfer color photographic film was prepared by successively coating a cellulose triacetate support with the following layers.
  • a cyan dye developer 5,8-dihydroxy-L4- bis[ (B-hydroquinonyl-a-methyl )ethylamino anthraquinone, was dissolved in a mixed solvent of 10 cc of N-n-butyl-acetanilide and 20 cc of ethyl acetate and the solution was dispersed by emulsification in 50 cc of a 10% aqueous gelatin solution containing 3 cc of sodium n-dodecylbenzenesulfonate.
  • Red-sensitive emulsion layer
  • Green-sensitive emulsion layer
  • a diffusion transfer color photographic material of this invention was prepared by following the same pro cedure as in the case of preparing Sample A except that 3 cc of a 1% methanol solution of N-methyl-benzmordant and 0.5
  • samples A and B were subjected to stage exposure, i.e., the film samples were exposed for 1/20 second with a 500 watt tungsten lamp using a green wedge filterand then exposed over all for l/200 second with the same lamp but using a red filter at a distance of 30 cm. on an intensity scale sensitometer.
  • the exposed film was processed using a liquid processing composition having the following formula while in superposed relationship with an image-receiving sheet prepared as described below.
  • Liquid processing composition :
  • the image-receiving sheet was prepared by coating a baryta-coated support with a gelatin layer containing a mixture of 100 grams of poly-4-vinylpyridine as a grams of l-phenyl-5- mereaptotetrazole to a dry thickness of microns.
  • FIG. 1 of the accompanying drawing shows the relationship between the relative exposure amount and the optical density of the image on the image-receiving sheet.
  • AG and AR are the curves resulting from Sample A when green light and red light were employed, respectively, while BG and BR are the curves resulting from Sample B when green light and red light were employed, respectively. From the results shown in FIG. 1, it will be understood that the variation of density measured using a red filter was less in Sample B than in Sample A. This shows that the development and transfer of the cyan dye developer were less influenced by the amount of green light exposure and further that an improved transfer density and a high color separation power were obtained.
  • a cellulose tn'acetate support was successively coated with the following layers to provide a diffusion transfer color photographic material.
  • l,4 bis (a-methyl-B- hydroxynonylpropylamine)-5,8-dihydroxyanthraquinone was dissolved in a mixture of 25 cc of N,N-diethyl laurylamide and 25 cc of methylcyclohexanone at 70C.
  • This solution was dispersed by emulsification in 160 cc of an aqueous 10% gelatin solution containing l0 cc of a 5% aqueous solution of sodium dodecylbenzenesulfonatc, and after further adding water to the emulsion to make the volume 500 cc, the resultant emulsion was coated on the support so that the dry thickness of the layer was 5 microns.
  • Red-sensitive emulsion layer
  • a red-sensitive silver iodobromide emulsion contain ing 5.5 X 10" mole of silver halide/ g of the silver halide emulsion and 5.0 g of gelatin was coated on the cyan developer layer so that the dry thickness of the layer was 3.5 microns.
  • Green-sensitive emulsion layer
  • a green-sensitive silver iodobromide emulsion containing 4.7 X 10 mole of silver halide/100 g of emulsion and 6.2 g of gelatin was coated on the magenta developer layer so that the dry thickness of the layer was 1.8 microns.
  • the solution was dispersed by emulsification in 100 cc ofa 10% aqueous gelatin solution containing 8 cc of a 5% aqueous solution of sodium ndodecylbenzene sulfonate, and after adding to the emulsion 5 cc of a 2% aqueous solution of 2-hydroxy- 4,6-dichloro-S-triazine and water to make the total vol ume 300 cc, the resultant emulsion was coated on the intermediate layer so that the dry thickness of the layer was 1.5 microns.
  • a blue-sensitive silver iodobromide emulsion containing 3.5 X 10 mole of silver halide/l00 g of emulsion and 6.5 g of gelatin was coated on the yellow dye developer layer so that the dry thickness of the layer was 1.5 microns.
  • The, l0 g of the emulsion thus prepared was mixed with 100 cc ofa 5% aqueous gelatin solution containing 5 cc ofa 2% aqueous solution of mucochloric acid, and the mixture was coated on the blue-sensitive emulsion layer so that the dry thickness of the layer was 1 micron.
  • a diffusion transfer color photographic material of this invention was prepared by following the same procedure as the case of preparing Sample C except that cc of a 171 methanol solution of N-benzylbehzthiazoline-2-thion (Compound 5) was incorporated in the blue-sensitive emulsion layer and 2 cc of the same methanol solution was incorporated in the greensensitive emulsion layer.
  • Each of samples C and D was subjected to a stage exposure using green light and then uniformly exposed using blue light and red light of an intermediate intensity.
  • the exposed film was subjected to a diffusion transfer using a liquid processing composition and image-receiving sheet the same as those in Example 1.
  • the reflection density of the color image transferred onto the image-receiving sheet was measured using a blue filter, a green filter, or a red filter, the results of which are shown in FIG. 2 of the accompanying drawing (FIG. 2 shows the same relationships as FIG. 1). From the results shown, it will be understood that the variation of the density measured by using the blue filter and red filter was less in Sample D than in Sample C. This shows that the development and image transfer of the yellow dye developer and the cyan dye developer were less influenced by the amount of green light exposure and also an improved transfer density and a high color separation power were obtained.
  • a cellulose triacetate support was coated successively with the following layers to provide a multilayer diffusion transfer color photographic material for comparison purposes.
  • Red-sensitive emulsion layer
  • a red-sensitive silver iodobromide emulsion containing 4.8 X 10 mole of silver halide/100 g of emulsion and 6.2 g of gelatin was coated onto the cyan dye developer layer so that the dry thickness of the layer was 3.0 microns.
  • a 5% aqueous gelatin solution containing 2.5 cc of a 5% aqueous solution of sodium n-dodecylbenzenesulfonate was coated onto the red-sensitive emulsion layer so that the dry thickness of the layer was 1.8 microns.
  • a blue-sensitive silver iodobromide emulsion containing 4.8 X 10" mole of silver halide/ g of emulsion and 6.2 g of gelatin was coated on the yellow dye developer layer so that the dry thickness of the layer was 1.8 microns.
  • Diffusion transfer color photographic materials of this invention were prepared following the procedure described above except that 3 cc of a 1% methanol solution of each of various compounds shown in the Table below was incorporated in the blue-sensitive emulsion layer.
  • Each of the samples was exposed uniformly to red light of an intermediate intensity and then subjected to a stage exposure using blue light.
  • the exposed film was subjected to diffusion transfer processing using a liquid processing composition and an image-receiving sheet the same as those used in Example 1.
  • the reflection density of the color image transferred onto the image receiving sheet was measured using a blue filter and a red filter and the results from samples containing the compounds of this invention were compared with the results from Sample E containing no compound of this invention.
  • the results of measuring the differences between the red density of Sample E and those of Samples F-Y containing the compounds of this invention at the exposure amount at which the blue density was minimized are shown in the following table as AD The larger the numerical value the more remarkable the superposed effect becomes.
  • Samples F to S containing the compounds of this invention exhibit remarkable multilayer affects and less variation in red density relative to the variation of blue density in comparison with variations in Sample E which does not contain the compounds of this inventionv
  • Samples F to S have an improved transfer density and high color resolution.
  • a diffusion transfer color photographic material comprising a support having thereon at least two layers each containing a dye developer, and having thereon at least two silver halide photographic emulsion layers, at least one of said silver halide photographic emulsion layers containing a compound represented by general formula l wherein Q represents an atomic group necessary for forming a heterocyclic ring, and R represents an unsubstituted alkyl group, an alkyl group substituted by a hydroxyl group, an aryl group or a morpholino group, an unsubstituted aryl group, an aryl group substituted by an alkyl group, an alkoxy group or a halogen atom or a heterocyclic group, said compound being capable of releasing a diffusible development inhibitor upon development of exposed silver halide by said dye developer, thereby causing imagewise release of said inhibitor upon development of said emulsion layers subsequent to exposure thereof,
  • the diffusion transfer color photographic material as set forth in claim 1 wherein said compound is a compound represented by the general formula la wherein X represents a sulfur atom, an oxygen atom. a selenium atom, a N-R group, or a CH CH group; A and B each represents a hydrogen atom, an unsubstituted alkyl group or an alkyl group substituted by a hydroxyl group or a halogen atom, an unsubstituted aryl group, an aryl group substituted by an alkyl group, a hydroxyl group or a halogen atom, an alkoxycarbonyl group, or an atomic group necessary for forming a saturated or unsaturated ring having 5-6 carbon atoms which may be substituted by an alkyl group, an aryl group, an alkoxy group or a halogen atom; and R and R" are independently the same as R of claim 1.
  • said layers containing dye developers are a layer containing cyan dye developer, a layer containing a magenta dye developer, and a layer containing a yellow dye developer;
  • said silver halide photographic emulsion layers are a red-sensitive emulsion layer, a green-sensitive emulsion layer, and a blue-sensitive emulsion layer, said red-sensitive emulsion layer being the lowermost silver halide emulsion layer;
  • said cyan developer layer is disposed adjacent to the red-sensitive emulsion layer at the support side, said magenta dye developer layer adjacent to the green-sensitive emulsion layer at the support side, and said yellow dye developer layer adjacent to said bluesensitive emulsion layer at the support side.
  • heterocyclic ring represented by group O of general formula l is a thiazolidine-Z-thion ring, an imidazolidineQ-thion ring, a selenazolidine-Z-thion ring, a 1,3,4-thidiazoline-2 thion ring, a 1,3,4-selenadiazoline-2-thion ring, a 4- thiazoline-Z-thion ring, a 4-selenazoline-2-thion ring, a 1,Z-dihydropyridine-2-thion ring, a benzthiazoline-Z- thion ring, a benzoxazoline2-thion ring, :1 benzimidazoline2thion ring, a benzselenazolineQ-thion ring, or a l,Z-dihydroquinoline-Z-thion ring and R is an alkyl group having 1-6 carbon atoms
  • a and B are selected from the group consisting of methyl, phenyl and ethoxycarbonyl
  • R and R represent an alkyl group having 1-6 carbon atoms, an alkyl group having l-6 carbon atoms substituted by a hydroxyl group, an aryl group, a morpholino group; an aryl group substituted by an alkyl group, an alkoxyl group, a halogen atom, or a Z-pyridyl, tetrazolyl, thiazolyl or triazolyl group.
  • R and R" represent an alkyl group having 1-6 carbon atoms, an alkyl group having l6 carbon atoms substituted by a hydroxyl group, an aryl group, a morpholino group; an aryl group substituted by an alkyl group, an aljkoxyl group, a halogen atom, or a 2-pyridyl, tetrazolyl, thiazolyl or triazolyl group.
  • R represents an alkyl group having 16 carbon atoms, an alkyl group having 16 carbon atoms substituted by a hydroxyl group, an aryl group, a morpholino group; an aryl group substituted by an alkyl group, an alkoxyl group, a halogen atom, or a 2-pyridyl, tetrazolyl, thiazolyl or triazolyl group.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
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  • Plural Heterocyclic Compounds (AREA)
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Cited By (2)

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US4086094A (en) * 1974-06-20 1978-04-25 Fuji Photo Film Co., Ltd. Photographic couplers with N-heterocyclic development inhibiting coupling-off group
US5032159A (en) * 1988-12-08 1991-07-16 Canon Kabushiki Kaisha Method of manufacturing optical device

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US3202512A (en) * 1962-02-23 1965-08-24 Eastman Kodak Co Photographic silver halide emulsions stabilized with tetrazaindene compounds
US3260597A (en) * 1960-12-02 1966-07-12 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers and development arrestors
US3265498A (en) * 1960-08-22 1966-08-09 Polaroid Corp Diffusion transfer photographic process utilizing development restrainers
US3330657A (en) * 1963-10-23 1967-07-11 Polaroid Corp Photographic products and processes utilizing 2, 5-dimercapto-1, 3, 4-thiadiazole as an antifoggant
US3674478A (en) * 1970-12-17 1972-07-04 Polaroid Corp Novel products and processes
US3698898A (en) * 1970-12-17 1972-10-17 Polaroid Corp Photographic products and processes employing a compound which in the presence of alkali releases a diffusible photographic reagent
US3723125A (en) * 1969-09-05 1973-03-27 Fuji Photo Film Co Ltd Process for the formation of color photographic images
US3736136A (en) * 1970-07-02 1973-05-29 Agfa Gevaert Ag Dye diffusion transfer process for the production of positive color photographic images
US3785813A (en) * 1972-01-03 1974-01-15 Polaroid Corp Polycyclic hydropyrimidine development restrainers

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US3265498A (en) * 1960-08-22 1966-08-09 Polaroid Corp Diffusion transfer photographic process utilizing development restrainers
US3260597A (en) * 1960-12-02 1966-07-12 Eastman Kodak Co Photographic multicolor diffusion transfer process using dye developers and development arrestors
US3114637A (en) * 1961-05-01 1963-12-17 Eastman Kodak Co Photographic emulsions stabilized with 1, 2-dithiacyclopent-3-enes
US3202512A (en) * 1962-02-23 1965-08-24 Eastman Kodak Co Photographic silver halide emulsions stabilized with tetrazaindene compounds
US3330657A (en) * 1963-10-23 1967-07-11 Polaroid Corp Photographic products and processes utilizing 2, 5-dimercapto-1, 3, 4-thiadiazole as an antifoggant
US3723125A (en) * 1969-09-05 1973-03-27 Fuji Photo Film Co Ltd Process for the formation of color photographic images
US3736136A (en) * 1970-07-02 1973-05-29 Agfa Gevaert Ag Dye diffusion transfer process for the production of positive color photographic images
US3674478A (en) * 1970-12-17 1972-07-04 Polaroid Corp Novel products and processes
US3698898A (en) * 1970-12-17 1972-10-17 Polaroid Corp Photographic products and processes employing a compound which in the presence of alkali releases a diffusible photographic reagent
US3785813A (en) * 1972-01-03 1974-01-15 Polaroid Corp Polycyclic hydropyrimidine development restrainers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4086094A (en) * 1974-06-20 1978-04-25 Fuji Photo Film Co., Ltd. Photographic couplers with N-heterocyclic development inhibiting coupling-off group
US5032159A (en) * 1988-12-08 1991-07-16 Canon Kabushiki Kaisha Method of manufacturing optical device

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JPS4846331A (ko) 1973-07-02
GB1363040A (en) 1974-08-14
JPS5423581B2 (ko) 1979-08-15
DE2250064A1 (de) 1973-04-19

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