US3928041A - Development inhibitor yielding compound for silver halide photography - Google Patents

Development inhibitor yielding compound for silver halide photography Download PDF

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Publication number
US3928041A
US3928041A US424831A US42483173A US3928041A US 3928041 A US3928041 A US 3928041A US 424831 A US424831 A US 424831A US 42483173 A US42483173 A US 42483173A US 3928041 A US3928041 A US 3928041A
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Prior art keywords
compound
photographic material
group
development
groups
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US424831A
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Mitsuto Fujiwhara
Takaya Endo
Ryosuke Satoh
Toyoaki Masukawa
Takahiro Uozumi
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Konica Minolta Inc
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Konica Minolta Inc
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Assigned to KONICA CORPORATION reassignment KONICA CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: KONISAIROKU PHOTO INDUSTRY CO., LTD.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • 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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/156—Precursor compound
    • Y10S430/158—Development inhibitor releaser, DIR

Definitions

  • ABSTRACT A light-sensitive silver halide photographic material is developed in the presence of a development inhibitoryielding compound having the formula wherein X is halogen COOR or, -OZ, where Z is an alkyl group, aryl group, heterocyclic ring residue, acyl group, or SO -R (R is an alkyl group, aryl group or heterocyclic ring residue) and R is an alkyl group; and R is where each of R is an aliphatic group or aryl group or two of the R groups may, together with the adjacent nitrogen atom, for a heterocyclic ring residue, and Y is a group which, when the thioether linkage has been split, forms, together with the sulfur atom, a compound having a development-inhibiting action.
  • This invention relates to a development inhibitor yielding compound for silver halide photography. It has heretofore been well known to incorporate into a lightsensitive silver halide photographic material a compound capable of yielding a development inhibitor, depending on the density of image at the time of development of the photographic material (the said compound will be referred to as development inhibitoryielding compound, hereinafter).
  • the said compound is, in general, of such a type that it reacts with the oxidation product of a color developer to yield a development inhibitor.
  • Typical of such a compound is the so-called DIR coupler that is prepared by introducing into the coupling position of a coupler a group capable of forming a compound showing a development-inhibiting effect when it is released from the coupling position.
  • This coupler has such properties that when coupled with the oxidation product of a color developing agent, it forms a dye and, on the other hand, yields a development inhibitor.
  • a development inhibitor-yielding compound is used, in general, for such purposes as mentioned below.
  • the compound has the characteristic that it yields a development inhibitor in correspondence to the density of image at the time of development.
  • the thus yielded development inhibitor is present in the emulsion layer of the photographic material, the development of said layer is inhibited in relation to the image density, so that there may be expected the so-called intra-image effects such as control of image tone, fine graininess of image, and improvement in sharpness of image.
  • a novel development inhibitor-yielding compound is used, whereby the abovementioned disadvantages are overcome, and prominent wherein X is halogen COOR or, OZ, where Z is an alkyl group, aryl group, heterocyclic ring residue, acyl group, or SO R (R is an alkyl group, aryl group or heterocyclic ring residue) and R is an alkyl group; and R is or -SY, where each of R is an aliphatic group or aryl group, or two of R groups may, together with an adjacent nitrogen atom, form a heterocyclic ring residue, and Y is a group which, when the sulfur atom of the thioether linkage has been released, forms together with the sulfur atom, a compound having a development-inhibiting effect.
  • the development inhibitor-yielding compound used in the present invention forms a colorless compound even when reacted with the oxidation product of the color-devoloping agent. Since the thus formed colorless compound does not constitute any part of'the resulting image, the compound used in the present invention has the advantage that it can be applied singly, without using other compounds different in structure,
  • the compound used in the present invention has an extremely high reactivity with the oxidation product of a color-developing agent, and hence has the advantage that excellent intra-image and inter-image effects can be attained even when the compound is used in a small amount.
  • the compound has the advantage that it can be selected from various development inhibitor-yielding compounds of the aforesaid general formula which may be used as photographic material and, in extreme cases, it can be incorporated into only one layer to act on all layers.
  • the diffusible compound can be incorporated also into a color developer.
  • non-diffusible compound is useful in the case where the intra-image and inter-image effects are desired to be imparted to a specific layer.
  • the said compound may be used so as to vary the concentration of component constituting the said layer.
  • Typical examples of the compound used in the pres- CO cH S l Er ent invention are compounds of the aforesaid general formula, in which the alkyl group represented by Z is 1 ⁇ I N preferably an alkyl group having I to 5 carbon atoms, 15
  • acyl group represented by Z is desirably 1] COR where R is preferably an alkyl or aryl group.
  • R is preferably an alkyl or aryl group.
  • the heterocyclic ring residue represented by any of Z and R is preferably a 5- or 6-membered heter- N-N ocyclic ring residue such as pyridine, furan or thio- (5) H phene, and the aliphatic group represented by R, i
  • the heterocyclic ring residue represented by R is a 5- or 6-membered heterocyclic group, which may have one or more of N N such different atoms as N, O and S and may have a condensed benzene or naphthalene ring. In case there are two or more groups represented by R, the said I groups may be different groups.
  • the nitrogemcontain- 0 ing heterocyclic ring which is formed by the combination of two groups represented by R in such a group as J SO N(R for example, is preferably a 5- to 6-membered ring. Typical examples of said ring are piperi- I dine, pyrrolidine and morpholine rings.
  • the aryl groups represented by Z, R;,, R and R are typically phenyl (5) (3OJQH S and naphthyl groups, and may have been substituted by ,1
  • alkyl groups represented by Z, R, and R, l
  • Y in the formula is 5 a group which, when the sulfur atom of the thioether linkage has been released, fomis, together with the N-N ll sulfur atom, an allyl-mercapto compound, a heterocyclic compound, a compound of the thioglycolic acid COH OCOCH series, or cysteine, glutathione or the like compound 5 T T having a development-inhibiting action.
  • Typical exam- COOC.,H ples of the mercapto compound represented by Y in- L 5 clude mercaptotetrazole type compounds, particularly 1-phenyl-2-mercaptotetrazole, l-nitrophenyl-S-mercaptotetrazole and l-naphthyl-S-mercaptotetrazole,
  • mercaptothiazole type compounds particularly 2-mer- T T captobenzothiazole and mercaptonaphthothiazole, mercaptooxadiazole type compounds, mercaptopiperi- ('7) C H CO-CH S dine type compounds, mercaptothiadiazole type compounds, particularly Z-mercaptothiadiazolotriazine, 5 mercaptotriazine type compounds, mercaptotriazole type compounds, and mercaptobenzene type com- Q pounds, particularly l-mercapto-Z-benzoic acid, l-
  • an alkyl group or a carbocyclic residue is also preferable as Y.
  • Typical examples of the carbocylic residue are phenyl and the (8) l l 29 like aryl groups, and cycloalkyl and the like alicyclic N-N groups.
  • the silver halides may have been prepared according to any processes adopted for preparation of the so-called conversion emulsions or Lippmanns emulsions.
  • the kind, grain size, content and mixing ratio of the silver halides vary depending on the nature of the photographic materials. In the case of relatively low speed photographic materials, the silver halides are composed mainly of silver chloride, while in the case of relatively high speed photographic materials, the content of silver chloride is low.
  • the silver halides are fogged either optically or chemically. Further, the silver halides may be chemically sensitized with one or more of such sensitizers as active gelatin, sulfur sensitizers, e.g.
  • gold sensitizers e.g. potassium chloroaurite, potassium aurithiocyanate, potassium chloroaurate and 2-aurosulfobenzothiazole metachloride
  • ruthenium, rhodium, palladium and iridium sensitizers e. g. ammonium chloropalladate, potassium chloroplatinate and sodium
  • the silver halides may be directly applied, in a binder-free form, onto a support by vacuum evaporation or the like.
  • the silver halides may be brought to the form of the so-called silver halide emulsions by dispersing them in a binder comprising one or more of gelatin and the like colloidal substances, e.g. colloidal albumin cellulose derivatives, and polyvinyl and the like synthetic resins, and applied onto a support, if necessary through sub layer, inter layer, etc.
  • the silver halide emulsions may be optically sensitized with, for example, cyanine or merocyanine dyes.
  • a color photographic material for example, there are used three kinds of silver halide emulsions which are different from each other in sensitive wave-length region. Furthermore, the silver halide emulsions may be stabilized with triazoles, azaindenes, quaternary benzothiazolium compounds, or zinc or cadmium compounds, and may contain sensitizing compounds of the quaternary ammonium or polyethylene glycol type.
  • the emulsions may further contain suitable gelatin stabilizers including glycerin, dihydroxyalkanes such as 1,5-pentadiol, esters of ethylenebis-glycolic acid, bisethoxydiethyleneglycol succinate, acid amides of the acrylic acid type, and latexes; gelatin hardeners including formaldehyde, halogen-substituted fatty acids such as mucobromic acid, compounds having acid anhydride groups, dicarboxylic acid chlorides, biesters of methanesulfonic acid, and sodium bisulfite derivatives of dialdehydes whose aldehyde groups are separated by 2 to 3 carbon atoms; extenders such as saponin; coating aids such as sulfosuccinates; and the like various photographic additives.
  • suitable gelatin stabilizers including glycerin, dihydroxyalkanes such as 1,5-pentadiol, esters of ethylenebis-glycolic acid
  • the emulsions contain couplers, e.g. S-pyrazolone type, magenta couplers, naphthol or phenol type cyan couplers, and yellow couplers having active methylene groups interposed between two carbonyls, which may be the so-called 2-equivalent or 4-equivalent couplers, and may contain the so-called masking couplers which have, for example, arylazo groups in the coupling positions.
  • the said masking couplers are preferably used in combination with the so-called colorless couplers, which are colorless before color development.
  • the emulsions may contain dispersing agents for the couplers used in the above case, e.g. coupler solvents for the so-called protect type couplers.
  • the emulsions may further contain, in combination with various couplers, the so-called competing couplers which can form leuco-dyes.
  • the emulsions may contain, in place of the couplers, dye developers or coupler developers.
  • the dye developers are compounds having both the functions of dyes and the functions of developers which are prepared by introducing hydroquinone or aromatic primary amino color developing agents into dyes
  • the coupler developers are compounds having both the functions of couplers and the functions of developers which are prepared by introducing hydroquinone or the like into the coupling positions or other portions of the aforesaid couplers.
  • the emulsions may contain dyes and, if necessary, ultraviolet absorbers, brighteners,
  • Such silver halide emulsion is applied onto a support, if necessary through sub layer, inter layer, etc., to prepare a light-sensitive silver halide photographic material.
  • the support used in this case includes paper, laminated paper, glass, and cellulose acetate, cellulose nitrate, polyester, polyamide and polyethylene films and sheets, and is properly selected according to the intended use of the photographic material.
  • a photographic material is composed of a support and a photosensitive layer (silver halide-deposited layer or emulsion layer).
  • the photographic material may have, depending on the intended use thereof, a sub layer, inter layer, filter layer, anti-curling layer, protective layer, etc. which have properly combined with each other.
  • the photosensitive layer itself may be composed of layers of emulsion varying in speed in the same or different wave-length region. These layers may contain various photographic additives, e.g. those incorporated into the aforesaid emulsions. Further, each layer may contain different additives, e.g. the filter layer may contain a filter dye, and the protective layer a film property-improving agent and an antistatic agent. As another embodiment, a diffusion transfer photographic material, for example, may have an inter layer contain- 1 1 ing a physical development nucleus.
  • the thus prepared silver halide photographic material is developed in the presence of a compound having the aforesaid general formula to show such excellent photographic properties as mentioned previously.
  • the compound of the diffusible type may be incorporated into any layers of the photographic material, e.g. into one or more of the emulsion layer, inter layer, protective layer, etc., and the compound of the non-diffusible type is desirably incorporated into the emulsion layer, or into one or more layers adjacent thereto.
  • the compound is added to a coating liquid for forming a layer of the photographic material.
  • the compound may be used in any form. That is, the diffusible compound may be used in the form of a solution, e.g. an aqueous alkali solution, while the non-diffusible compound may be used in the form of an emulsion, e.g. an emulsion in the aforesaid coupler solvent.
  • the coupler solvent is, in general, a water-immiscible high boiling organic solvent such as di-n-butyl phthalate, benzyl phthalate, triphenyl phosphate, tri-o-cresyl phosphate or monodiphenyI-p-tbutylphenyl phosphate, or a mixture thereof with a low boiling solvent such as methyl isobutyl ketone, ,B-ethoxyethyl acetate, methoxytriglycol acetate, acetone, methylacetone, methanol, ethanol, acetonitrile, dioxane, dimethylformamide, ethyl acetate, isopropyl acetate or chloroform.
  • the low boiling organic solvent may be used in place of the high boiling organic solvent.
  • the above-mentioned organic solvents may be used either singly or in the form of a mixture of 2 or more members.
  • a diffusion transfer photographic material for example, is developed in close contact with other photographic material, e.g. an image-receiving material.
  • a compound of the aforesaid general formula may have been incorporated into said other photographic material.
  • the compound used in this case is desirably of the diffusible type.
  • the non-diffusible compound may also be used in the case where the image-receiving material is of such a type that silver halide particles on the physical development nucleus are to be adhered to the image-receiving layer (e.g. gelatin layer or polyvinyl resin layer) on the support.
  • a compound of the aforesaid general formula is incorporated into a photographic material, or other photographic material such as an image-receiving material.
  • the compound may be protected, depending on the kind of substituents thereof, with a carrier such as a mordant, and confined in a specific layer until the compound is required.
  • a carrier such as a mordant
  • a compound having anion groups may be protected with amino groups in a certain mordant, and liberated at the time of development.
  • a compound of the aforesaid general formula may be incorporated into a developer or a pretreating solution for the developer.
  • said developer and pre-treating solution are black-white developers, color developers, e.g. ordinary color developers for the color films of the couplerincorporated type and the non-incorporated type, one or both of first and second developers in the case of reversal development, ordinary black-white developers and X-ray developers, and pre-treating solutions such as pre-hardening solutions.
  • the compound used in the above case is desirably a diffusible compound, in general. It is also possible that a carrier is previously incorporated into a specific layer of photographic material to emphasize the effect of said layer.
  • the developer preferably contains an aromatic primary amino color developing agent.
  • the compounds of the aforesaid general formula are used in such various modes as mentioned above. All the compounds can give more excellent image effects than in the case where the conventional development inhibitor-yielding compounds are used. The effects are particularly marked when the compounds are incorporated into photographic materials.
  • the amount of the compound used in the present invention varies depending on the application procedure, the intended use and the desired effect, but is preferably in the range from 0.1 to 10 g. per kg. of the emulsion. In case the compound is used in an amount equal to that of the conventional development inhibitor-yielding compound, the image effects become far greater than those attained by the conventional compound. For the attainment of the same-image effects as those attained by the conventional 1 compound, the compound may be used in an extremely small amount.
  • composition of a developer which has been incorporated with the compound of the aforesaid general formula, is as follows:
  • the above-mentioned developers are controlled in pH and further incorporated with various other photographic additives.
  • compositions of the said developers are as follows:
  • a photographic material having a layer incorporated with a non-diffusible compound of the aforesaid general formula may be treated with a processing solution containing a diffusible compound of the aforesaid general formula.
  • a photographic material which has been developed in the above-mentioned manner according to the present invention, is then subjected to an ordinary photographic treatment comprising a suitable combination of steps selected from, for example, stopping, stop-fixing, fixing, bleaching, bleach-fixing, stabilizing, water-washing and drying steps.
  • Sample II For comparison, a sample [I was prepared in the same manner as above, except that compound l) was not used.
  • N,N-Dimethyl p-phenylenediamine hydrochloride 2.0 g.
  • Anhydrous sodium sulfite 2.0 g.
  • Sodium carbonate (monohydrate) 82.0 g.
  • Potassium bromide 2.0 g. Water to make liter
  • both of the samples formed images comprising a magenta dye.
  • the two samples were identical in speed, but the y-value of sample II was 0.9 and that of the sample I was 0.5.
  • the grains constituting the magenta image of the sample II were considerably finer than in the case of sample 1.
  • Sample IV For comparison, a sample IV was prepared in the same manner as above, except that the green-sensitive emulsion contained only the magenta coupler and did not contain compound (9).
  • Samples Ill and IV were individually exposed through an optical wedge to red light and white light, developed with the same developer as in Example 1, and then subjected to ordinary bleach-fixing treatment.
  • a mixture comprising 0.8 g. of compound (9), 0.8 cc. of 2,4-di-n-amylphenol and 0.8 cc. of dimethylformamide was heated with stirring at 80C. to form a solution.
  • This solution was mixed at 40C. with 20 cc. of a 10% aqueous gelatin solution and 2 cc. .of a 5% aqueous Alkanol B solution, and the resulting suspension was subjected 5 times to a colloid mill to form a dispersion.
  • the thus prepared emulsion was stirred for 2 minutes, allowed to stand at 40C. for 30 minutes, and then coated on the aforesaid fogged emulsion layer to prepare a light-sensitive film.
  • the above-mentioned light-sensitive film was contacted with the image receiving layer of the image-receiving film, and then developed with a developer of the following composition:
  • EXAMPLE 4 A sample was prepared by forming on a triacetate base the following layers in the order shown below (weight per 900 cm l.
  • a red-sensitive silver iodobromide emulsion layer containing 440 mg. of gelatin and 174 mg. of silver halide.
  • the emulsion layer additionally contained 26.3 mg. of l-hydroxy-4-(4-t-butylphenoxy)-4-phenylazo- 2-naphthanilide and 32.7 mg. of l-hydroxy-N-[oz-(2,4- di-t-amylphenoxy)butyl-Z-naphthamide] as couplers, and 7 mg. of the compound (23).
  • a green-sensitive silver iodobromide emulsion layer containing 400 mg. of gelatin and 243' mg. of silver halide.
  • the emulsion layer additionally contained 24.5 mg. of l-(2,4,6-trichlorophenyl)-3- ⁇ 3 [a-(2,4-dit-amylphenoxy)acetamide] benzamide ⁇ -4-(4-methox- 16 yphenylazo)-5-pyrazolone and 24.3 mg. of l-(2,4,6-trichlorophenyl )-3 3-[ a-( 2,4-di-t-amylphenoxy )acetamide] benzamide ⁇ -5-pyrazolone as c0uplers,-and 7 mg. of the compound (23).
  • emulsion layer further contained 8.7 mg. of dioctyl hydroquinone as an anti-stain agent.
  • a blue-sensitive silver halide emulsion layer containing 200 mg. of gelatin and 62 mg. of silver halide.
  • the emulsion layer additionally contained 102.5 mg. of N-(p-benzoylacetamidobenzenesulfonyl )-N-( a-phenylpropyl)-p-toluidine as a coupler and 2.3 mg. of dioctyl hydroquinone as an anti-stain agent.
  • the former sample according to the present invention which contained compound (23) had more excellent sharpness, and granularity and lessfog than the latter sample.
  • sulting solution was mixed with20 ml. of a lO%,aque-.
  • the image formed according to the present invention was far more excellent, due to the prominent image effects displayed by compound (24), in sharpness and granularity and more brilliant in hue than the image formed in the film treated in the absence of compound (24).
  • a method for development of an imagewiseexposed light-sensitive silver halide photographic material which comprises subjecting the imagewise-exposed light-sensitive silver halide photographic material to development in the presence of a development inhibitor-yielding compound having the formula wherein X is halogen, COOR or OZ, where Z is an alkyl group, aryl group, heterocyclic ring residue, acyl group, or SO R R is an alkyl group, aryl group or heterocyclic ring residue and R is an alkyl group; and R is where each R, is an aliphatic group or an aryl group or two of the R, groups may, together with the adjacent nitrogen atom, form a heterocyclic ring residue, and Y is a group which, when the thioether linkage has been split, forms, together with the sulfur atom, a compound having a development-inhibiting action.
  • aryl groups are selected from the group consisting of phenyl and naphthyl groups optionally substituted by halogens, hydroxy groups, alkoxy groups or alkyl groups.
  • a photographic material according to claim 2 wherein the compound having a development-inhibiting action is selected from the group consisting of 1- phenyl-2-mercaptotetrazole, l-nitrophenyl-S-mercaptotetrazole, lnaphthyl-S-mercaptotetrazole, 2-mercaptobenzothiazole, mercaptonaphthothiazole, mercaptooxadiazoles, mercaptopiperidines, mercaptothiadiazoles, mercaptotriazines, mercaptotriazoles, lmercapto-Z-benzoic acid, 1mercapto-Z-nitrobenzene and 1mercapto-3heptadecanoylaminobenzene.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
US424831A 1972-12-18 1973-12-14 Development inhibitor yielding compound for silver halide photography Expired - Lifetime US3928041A (en)

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US4046574A (en) * 1975-01-24 1977-09-06 Agfa-Gevaert, Aktiengesellschaft Color photographic material with homophthalimide thioether development inhibitor
US4049455A (en) * 1975-08-15 1977-09-20 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic material
US4063950A (en) * 1974-07-06 1977-12-20 Konishiroku Photo Industry Co., Ltd. DIR coupler that forms colorless reaction product
US4075021A (en) * 1974-10-25 1978-02-21 Konishiroku Photo Industry Co., Ltd. Photosensitive material for color photography
US4108663A (en) * 1975-11-07 1978-08-22 Fuji Photo Film Co., Ltd. Photographic developing agents, process for developing using same, and light-sensitive materials containing same
US4226934A (en) * 1977-08-12 1980-10-07 Ciba-Geigy Ag Light sensitive photographic material containing development inhibitor releasing compounds
US4306015A (en) * 1978-01-26 1981-12-15 Ciba-Geigy Ag Color photographic material
US4355100A (en) * 1980-01-16 1982-10-19 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4480028A (en) * 1982-02-03 1984-10-30 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic light-sensitive material
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
EP0201033A2 (en) 1985-04-30 1986-11-12 Konica Corporation A method for processing silver halide color photographic materials
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US6045985A (en) * 1997-12-02 2000-04-04 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Light-sensitive silver halide photographic elements containing yellow filter dyes
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DE2709688A1 (de) * 1977-03-05 1978-09-07 Agfa Gevaert Ag Lichtempfindliches farbphotographisches material
JPS60190930U (ja) * 1984-05-29 1985-12-18 カルソニックカンセイ株式会社 自動車用排気系に於けるデユアルタイプのフロントチユ−ブ
JPS6132839A (ja) * 1984-07-26 1986-02-15 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH01237543A (ja) * 1988-03-17 1989-09-22 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
US5994037A (en) * 1998-10-21 1999-11-30 Eastman Kodak Company Method for rapid photographic processing with maintained color balance using diffusible photochemicals
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US4063950A (en) * 1974-07-06 1977-12-20 Konishiroku Photo Industry Co., Ltd. DIR coupler that forms colorless reaction product
US4075021A (en) * 1974-10-25 1978-02-21 Konishiroku Photo Industry Co., Ltd. Photosensitive material for color photography
US4046574A (en) * 1975-01-24 1977-09-06 Agfa-Gevaert, Aktiengesellschaft Color photographic material with homophthalimide thioether development inhibitor
US4049455A (en) * 1975-08-15 1977-09-20 Konishiroku Photo Industry Co., Ltd. Light-sensitive silver halide photographic material
US4108663A (en) * 1975-11-07 1978-08-22 Fuji Photo Film Co., Ltd. Photographic developing agents, process for developing using same, and light-sensitive materials containing same
US4226934A (en) * 1977-08-12 1980-10-07 Ciba-Geigy Ag Light sensitive photographic material containing development inhibitor releasing compounds
US4306015A (en) * 1978-01-26 1981-12-15 Ciba-Geigy Ag Color photographic material
USRE31893E (en) * 1980-01-16 1985-05-21 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
US4355100A (en) * 1980-01-16 1982-10-19 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
US4480028A (en) * 1982-02-03 1984-10-30 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic light-sensitive material
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
EP0201033A2 (en) 1985-04-30 1986-11-12 Konica Corporation A method for processing silver halide color photographic materials
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US6045985A (en) * 1997-12-02 2000-04-04 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Light-sensitive silver halide photographic elements containing yellow filter dyes
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images

Also Published As

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JPS4984439A (ja) 1974-08-14
DE2362752C2 (de) 1984-03-29
DE2362752A1 (de) 1974-07-11
GB1450200A (en) 1976-09-22
JPS5116142B2 (ja) 1976-05-21

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Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302

Effective date: 19871021