GB2244053A - Magenta colour couplers - Google Patents

Magenta colour couplers Download PDF

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Publication number
GB2244053A
GB2244053A GB9011102A GB9011102A GB2244053A GB 2244053 A GB2244053 A GB 2244053A GB 9011102 A GB9011102 A GB 9011102A GB 9011102 A GB9011102 A GB 9011102A GB 2244053 A GB2244053 A GB 2244053A
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Prior art keywords
group
carbon atoms
hydrogen
alkyl
aryl group
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GB9011102D0 (en
GB2244053B (en
Inventor
William Edward Long
Kenneth Miller Mccombe
Raymond Geoffrey Noxan
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Ilford Imaging UK Ltd
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Ilford Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
    • 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
    • G03C7/30541—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the released group
    • G03C7/30552—Mercapto
    • 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
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/38—Couplers containing compounds with active methylene groups in rings
    • G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings

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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)

Abstract

Pyrazolone colour couplers of formula I:- <IMAGE> in which R1 is an aryl group, R2 is a ballasting group, R3 is -SO2R5 of -COR5, R4 is hydrogen or is combined with R3 to form a substituted imide ring, X is hydrogen, chlorine, or a group -COOR6 or -CONR6R7, Y and Z are each hydrogen, halogen, alkyl or a group COOR6, CONR6R7 or OR6, except that if X is chlorine Y and Z are not a group -OR6, and the groups R5, R6 and R7 are each an alkyl or aryl group or a substituted alkyl or aryl group with up to 18 carbon atoms, and with a total of 8-18 carbon atoms between the groups R5, R6 and R7, or R7 is hydrogen or is combined with R6 to from a ring, may be incorporated into silver halide photographic material.

Description

PHOTOGRAPHIC COLOUR COUPLERS This invention relates to novel pyrazolone compounds and to their use in photographic assemblies.
It is well known that pyrazolone compounds can be used as magenta couplers in photographic systems, as described, for example, by L J Fleckenstein in the book the Theory of the Photographic Process edited by T H James, 4th Edition, pages 356 and 357. The pyrazolone compounds used to date are usually the type known as four-equivalent couplers. However, it is known that there are disadvantages in the use of such compounds, for not only are four equivalents of silver necessary in order to produce each molecule of dye, but also the couplers themselves are sensitive to certain chemical vapours, for example formaldehyde, and this reduces the achievable density of magenta dye. These drawbacks can be overcome by the use of so-called two-equivalent pyrazolone couplers in which the coupling site is substituted with a leaving group.Suitable leaving groups for this purpose are known according for example to British patent specification 1 494 777 and 2 086 597 and US patent specification 4 556 630 but it has proved difficult to prepare and use successfully such 2-equivalent couplers.
One of the reasons for this difficulty is that it has been found that the rate-determining step of the coupling reaction of such compounds is the elimination reaction in which the leaving group is expelled, as described by Ichijima and Furutachi in the 1982 International Congress of Photographic Science paper 4-18 and by Kapecki et al in the 2nd International East West Symposium on the factors influencing photographic sensitivity, Hawaii 1988 paper D3.
This slow elimination step is the limiting factor in the use of such 2-equivalent pyrazolones under certain circumstances.
This is particularly true in the case of so-called chromogenic monochrome film, in which a mixture of couplers is used to produce the monochrome image. This is because any delayed production of magenta dye caused by the slow elimination reaction is not only unacceptable in itself, but also causes a concomitant loss of density in the cyan dye, which is located in the same oil droplets. We have found new 2-equivalent pyrazolone magenta colour couplers for which the slow elimination step of the coupling reaction is no longer a limiting factor in their use in photographic assemblies and which can be prepared more directly than those previously known.
Therefore, according to the present invention there is provided a pyrazolone colour coupler of general formula I :
in which RX is an aryl group, R2 is a ballasting group, R3 is -SO2R5 or-COR5, R4 is hydrogen or is combined with R3 to form a substituted imide ring, X is hydrogen, chlorine, or a group-COOR6 or -CONR6R7, Y and Z are each hydrogen, halogen, alkyl, or a group-COOR6, -CONR6R7, or -OR6, except that if X is chlorine Y and Z are not a group -OR6, and the groups R5, R6 and R7 are each an alkyl or aryl group or a substituted alkyl or aryl group with up to 18 carbon atoms, and with a total of 8-18 carbon atoms between the groups R5, R6 and R7 is hydrogen or is combined with R6 to form a ring.
The aryl group Rt is preferably a phenyl group or a substituted aryl group. Preferably the substitution is in the 2, 4 and 6 positions by halogen, lower alkyl, or lower alkoxy groups, in which a lower alkyl or alkoxy group is a group with up to 4 carbon atoms. Particularly suitable Rt groups are 2,4, 6-trichlorophenyl, 2, 4-dichloro-6-methylphenyl and 2,6-dichloro-4-methoxy phenyl.
Examples of rings which R6 and R7 may form are morpholine or piperidine rings which are optionally substituted for example by alkyl or alkoxy groups containing up to 4 carbon atoms.
The ballasting group R2 may consist of an organic ballasting group with at least 14 carbon atoms, or may consist of a polymeric chain.
If the group R2 is an organic ballasting group then preferably it is an aryl group of the formula:
in which R9 is a hydrogen, chlorine, substituted amine, lower alkyl, lower alkoxy or lower alkylthio group, and R8 is a nitrogen - linked ballasting group comprising 8-30 carbon atoms.
By lower alkyl or substituted alkyl group is meant a group comprising up to 6 carbon atoms.
Preferably R8 comprises an alkanoyl amino group having at least 8 carbon atoms. A particularly suitable group is the myristoyl amino group which comprises 14 carbon atoms. Another useful group R8 is a ballasted sulphonylamino group, for example hexadecyl sulphonylamino. Yet another suitable R8 ballasting group is a substituted alkanoyl amino group where the oil-solubilising substituent is an aryloxy group for example di-tertiary-amyl phenoxy acetyl. Another useful group R8 is a ballasted succinimido group.
Ballasting groups of the above types are well known in the art.
If the ballasting group R2 is a polymeric chain then preferably it is a group R10-L-CO- or a group R10-L-S02- in which L is a link which may be a direct link, or a phenylene or alkylene link such as a methylene group and R10 is a polymer chain prepared by polymerisation of ethylenically unsaturated monomers, such as methyl methacrylate with typically 100 repeating monomer units.
If the groups R3 and Ra are combined to make up an imide ring then the substituent on this group is a ballasting group having 8-18 carbon atoms, for example octadecyl succinimido or octadecenyl succinimido.
The pyrazolone compound of formula I may be prepared by routes known in the literature, and in particular by the methods described in British Patent Specification 2 086 597 and elsewhere which involve the reaction of a 4-equivalent pyrazolone coupler of formula II:
in which the groups RX and R2 are as defined above except that if the group R2 in formula I is a polymeric group then the group R2 in formula II includes the ethylenically unsaturated monomer necessary to prepare the polymer with a sulphenyl chloride of general formula III:
in which X, Y, Z, R3 and RA have the meanings assigned above.
The sulphenyl chlorides of general formula III may be prepared by known methods, and in particular by chlorination of the corresponding thiols or disulphides. These thiols or disulphides may be prepared in particular by reaction of an amino diphenyl disulphide of formula IV:
with a suitable acid derivative such as an acid chloride of the formula R3 C1 when Ra is hydrogen.
The disulphides of formula IV may be prepared by known routes, for example as described in Organic Synthesis, Collective Volume 3, pages 86 and 87.
The four-equivalent couplers of formula II are known compounds.
It is to be understood that the compounds of formula I are potentially tautometric, and that other tautomers may be involved under some circumstances.
According to another aspect of the present invention there is provided silver halide photographic material which comprises in at least one layer at least one pyrazolone colour coupler of general formula I. The photographic material may be the normal tripack colour photographic material comprising at least one blue light sensitive layer which comprises a yellow dye-yielding colour coupler, at least one red light sensitive layer which comprises a cyan dye-yielding colour coupler and at least one green light sensitive layer which comprises a magenta dye-yielding colour coupler of formula I.
All yellow and cyan colour couplers known in the art can be used.
Preferably however the photographic material of this aspect of the present invention is a so-called chromogenic monochrome material in which there is present a plurality of colour couplers which form a dye image rather than a silver image, which dye image is an almost grainless image which can be used for enlarging purposes. Such material is described in European Patent Application 25775.
As described in European Patent Application 25775 there is present in the chromogenic monochrome material preferably a yellow colour coupler, a cyan colour coupler and a magenta colour coupler. Most preferably the chromogenic monochrome material comprises two silver halide emulsion layers each of which comprises a yellow colour coupler, a cyan colour coupler and a magenta colour coupler of formula I as hereinbefore set forth.
These colour couplers are preferably dispersed in a solvent as described in US patent specification 3676137.
An organic solvent is preferably employed which is capable of dissolving the coupler, scarcely soluble in water, having a high boiling point and which remains together with the coupler in the photographic light-sensitive material containing the emulsion. Suitable solvent include substituted hydrocarbons, carboxylic acid ester, carboxylic acid amides, phosphoric acid ester and ethers. Specific examples include di-n-butylphthalate, N-N-diethyldodecanamide, and tricresylphosphate.
In addition to the high boiling solvent, there are sometimes used auxiliary solvents for dissolving the coupler, which solvents can be removed during the production of the photographic light-sensitive material. Specific examples of auxiliary solvent include isopropyl alcohol, ethyl acetate, butyl acetate, cyclohexanol, tetrahydrofuran and cyclohexanone.
Sometimes a surface active agent is used as an aid to disperse the oil soluble coupler in the photographic emulsion, and particularly, an anionic surface active agent such as sodium cetylsulphate, sodium p-dodecylbenzenesulphonate, or sodium di(2-ethylhexyl)-sulphosuccinate, or nonionic surface active agents such as sorbitan sesquioleic acid esters or sorbitan monolauric acid esters.
To disperse an oil-soluble coupler, an emulsifying homogenizer, a colloid mill or an ultrasonic emulsifying apparatus may be employed.
The photographic material of the present invention may be coated on any of the usual film bases including cellulose triacetate, cellulose acetate-butyrate and subbed and oriented polyethylene terephthalate. Preferably the silver halide used is an iodobromide silver halide having a halide ratio of from 1.5 to 10% of iodide to bromide.
Preferably the silver halide is panchromatically sensitised using both at least one green optical sensitising dye and at least on red optical sensitising dye.
The silver halide emulsion may be chemically sensitised by sulphur and/or gold sensitisers and also by polyethylene oxide compounds or by other sensitising agents used to sensitise high speed camera film emulsions.
The silver halide emulsion may be stabilised by the presence of stabilising compounds used to stabilise such emulsions, such as tetrazaindene compounds and mercaptotetrazole compounds.
The binder for the silver halide crystals in the silver halide emulsion is preferably gelatin but so-called gelatin extenders may be present such as acrylamides and polyvinyl alcohol.
Latex polymers may also be present such as latex polymers derived from alkyl acrylates and methacrylates.
The binder may be hardened using any of the well known hardeners such as formaldehyde, glyoxal, vinyl sulphones and triazine derivatives.
Conventional chromogenic processing baths can be used to develop the monochromatic material. The developer bath as a rule contains a developer substance of the p-phenylenediamine type, a development retarder, such as potassium bromide, an antioxidant, such as sodium sulphite, and a base, for example an alkali metal hydroxide or alkali metal carbonate.
The following are specific compounds of the present invention: COMPOUND A
COMPOUND B
COMPOUND C
COMPOUND D
COMPOUND E
COMPOUND F
COMPOUND G
A suitable monomer for preparing polymer couplers is Compound H.
COMPOUND H
The following examples will serve further to illustrate the invention: EXAMPLE 1 - SYNTHESIS EXAMPLE Synthesis of Compound B by the following synthesis route:
Intermediate (i) (prepared according to British Patent Specification 1 438 096) (6.35g) was dried by heating in toluene (220ml) under reflux. Myristoyl chloride (lOg) in toluene (3oil) was added over 5 minutes under nitrogen, which gave a precipitate which redissolved over 1 hour. After 3 hours toluene (50ml) was distilled out, and intermediate (ii) crystallised on cooling yield 14.2g (96%) mp 112.5-114 .
Sulphuryl chloride (0.95ml) in dichloromethane (5ml) was added over 10 minutes to a stirred suspension of intermediate (ii) (7.38g) in dichloromethane (30ml). The resulting amber solution was stirred for 30 minutes and then the solvent and excess reagent removed in vacuo. The residual sulphenyl chloride was taken up in dichloromethane (25ml) and added to intermediate (iii) (prepared according to US Patent 3 684 514) (14.73g) in dichloromethane (50ml) and triethylamine (llml).
There was a slight exotherm on addition and the reaction was then heated under reflux for 2 hours. The resulting solution was washed with dilute hydrochloric acid while still warm and ethyl acetate (25my) and dichloromethane (25my) added. The warm solution was washed with dilute hydrochloric acid and warm water, and the product Compound B crystallised out on cooling yield 12p mp 188-190 .
10.2g of the crude Compound B above was recrystallised from ethyl acetate (125ml), yield 8.65g mp 192-1940, found C 62.3, H 7.0, N 6.4%. Cs7H76Cl5N5Oa requires C 62.0, H 6.9, N 6.3%.
The following additional compounds were prepared analogously: COMPOUND mp C A 125.5 - 127.5 C 165 - 166.5 D 164.5 - 166 E 165 - 169 F 183 - 186 G 146 - 148 H 205 EXAMPLE 2 - EXAMPLE OF USE A series of model chromogenic monochrome film assemblies were prepared. The magenta colour coupler under test (Compound A, B, C, D or M) was dissolved in triarylphosphate oil with the aid of ethyl acetate, and the additional couplers, Compounds N, O and P were also dissolved in the oil. This oil was then dispersed in gelatin and coated with a conventional silver iodobromide photographic emulsion to give the following coating weights: SILVER 52mq/dm 2 Compound N Naphthol cyan coupler 2.3 Compound O Yellow coupler 6.3 Compound P Phenol cyan coupler 5.8 Test Magenta coupler ca 6.0* * Depending on molecular weight.
The other compounds used in the above test had the following structures: COMPOUND M - CONTROL MAGENTA COUPLER (Coupler Cp-6 of British Patent Application GB 2 086 597 A).
COMPOUND N - NAPHTHOL CYAN COUPLER
COMPOUND O - YELLOW COUPLER
COMPOUND P - PHENOL CYAN COUPLER
Samples of these coatings were then exposed for 1/30 seconds to a daylight wedge exposure of 250 lux and processed using conventional colour processing conditions.
The colour processing employed was as follows:1. Colour Developing 3 1/4 minutes Developer Bath: Potassium carbonate 37.5 g Sodium metabisulphite (anhydrous) 4.25 g Potassium iodi#e 2.0 mg Sodium bromide 1.3 g Hydroxylamine sulphate 2.0 g 4-(N-ethyl-N-2-hydroxyethylamino) 2-methylaniline sulphate 4.75 g Water to 1 litre 2. Bleaching 6 1/2 minutes Bleaching Bath Ammonium bromide 150 g Ammonium salt Df the Iron-Ill complex of ethylenediamine tetra-acedic acid 175 ml Acetic acid (glacial acetic acid) 10.5 g Sodium nitrate 35 g Water to 1 litre 3. Washing 3 1/4 minutes 4.Fixing 6 1/2 minutes Fixing Bath: Ammonium thiosulphate 16.2 ml (50% aqueous) diethylenetriaminepehta-acetic acid 1.25 g Sodium metabisulphite (anhydrous) 12.4 g Sodium hydroxide 2.4 g Water to 1 litre 5. Washing 3 1/2 minutes The density and contrast of the yellow, magenta and cyan dye images of the processed samples were measured immediately after processing.
The processed samples were then incubated for 24 hours. This incubation is sufficient to complete the elimination step of the leaving group of the two-equivalent magenta couplers. The density and contrast of the incubated samples were then measured again. An increase in density and contrast of the magenta dye image after incubation is a disadvantage, since it reveals that the magenta dye image was not fully formed after the standard processing conditions.
It will be seen that the control magenta coupler Compound M shows a considerable increase in density and contrast on incubation due to incomplete production of dye, whereas the inventive Compounds A, B, C and D show practically no increase.
RESULTS
DENSITY CONTRAST INCREASE ON INCUBATION COMPOUND COATING Y M C Y M C MAGENTA MAGENTA WEIGHT DENSITY CONTRAST mg/dm M 5.7 1.47 1.43 2.14 0.80 0.75 1.09 0.30 0.18 A 6.7 1.67 2.38 2.21 0.86 1.20 1.11 0.02 0.01 B 6.9 1.62 .06 2.20 0.85 1.06 1.09 0.03 0.02 C 5.4 1.62 1.70 2.05 0.79 0.82 0.96 0.02 0.01 D 5.6 1.39 1.24 1.90 0.72 0.61 0.92 0.03 0.01

Claims (9)

  1. CLAIMS: 1. A pyrazolone compound of general formula I:
    in which Rt is an aryl group, R2 is a ballasting group, R3 is -SO2R5 or -CORs, Ra is hydrogen or is combined with R3 to form a substituted imide ring, X is hydrogen, chlorine, or a group -COOR6, or -CONR6R7, Y and Z are each hydrogen, halogen, alkyl, or a group -COOR6, -CONR6R7, or -OR6, except that if X is chlorine Y and Z are not a group -OR6 and the groups R5, R6 and R7 are each an alkyl or aryl group or a substituted alkyl or aryl group with up to 18 carbon atoms, and with a total of 8-18 carbon atoms between the groups RS, R6 and R7, or R7 is hydrogen or is combined with R6 to form a ring.
  2. 2. A pyrazolone compound according to Claim 1 wherein RX is a phenyl or substituted aryl group.
  3. 3. A pyrazolone compound according to Claim 2 wherein the aryl group is substituted in 2, 4 and 6 positions by halogen, lower alkyl or lower alkoxy groups in which the alkyl moiety has up to four carbon atoms.
  4. 4. A pyrazolone compound according to any one of Claims 1 to 3 wherein R2 is either an organic ballasting group with at least 14 carbon atoms or a polymeric chain.
  5. 5. A pyrazolone compound according to Claim 4 wherein the organic ballasting group is an aryl group of the formula:
    in which R9 is a hydrogen, chlorine, substituted amino, lower alkyl, lower alkoxy or lower alkylthio group, and R8 is a nitrogen-linked ballasting group comprising 8-30 carbon atoms.
  6. 6. A pyrazolone compound according to Claim 5 wherein R8 comprises an alkanoyl amino group having at least 8 carbon atoms.
  7. 7. Silver halide photographic material at least one layer of which contains at least one pyrazolone compound as claimed in Claim 1.
  8. 8. Silver halide photographic material according to Claim 7 which comprises at least one blue light sensitive layer which comprises a yellow dye yielding colour coupler, at least one red light sensitive layer which comprises a cyan dye yielding colour coupler and at least one green light sensitive layer which comprises a magenta dye yielding colour which is a pyrazolone compound as claimed in Claim 1.
  9. 9. Silver halide photographic material according to Claim 7 which comprises at least one silver halide layer which contains at least one magenta dye yielding pyrazolone colour coupler as defined in Claim 1, at least one yellow dye yielding colour coupler and at least one cyan dye yielding colour coupler, the colour couplers being dissolved in a high boiling point organic solvent.
GB9011102A 1990-05-17 1990-05-17 Pyrazolone colour couplers Expired - Fee Related GB2244053B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5411841A (en) * 1993-05-24 1995-05-02 Eastman Kodak Company Photographic elements containing magenta couplers and process for using same
EP0763774A1 (en) * 1995-09-18 1997-03-19 Minnesota Mining And Manufacturing Company Process for preparation of 2-equivalent 4-arylthio-5-pyrazolone magenta couplers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1494777A (en) * 1974-03-11 1977-12-14 Fuji Photo Film Co Ltd Photographic silver halide emulsions containing couplers
GB2136980A (en) * 1983-02-08 1984-09-26 Kodak Ltd Sensitive silver halide photothermographic materials for producing dye images
DE3440138A1 (en) * 1983-11-04 1985-05-15 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Process for producing colour images
US4556630A (en) * 1983-06-20 1985-12-03 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
JPS6198350A (en) * 1984-10-19 1986-05-16 Konishiroku Photo Ind Co Ltd Silver halide color photographic sensitive material
EP0127162B1 (en) * 1983-05-25 1989-11-15 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1494777A (en) * 1974-03-11 1977-12-14 Fuji Photo Film Co Ltd Photographic silver halide emulsions containing couplers
GB2136980A (en) * 1983-02-08 1984-09-26 Kodak Ltd Sensitive silver halide photothermographic materials for producing dye images
EP0127162B1 (en) * 1983-05-25 1989-11-15 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4556630A (en) * 1983-06-20 1985-12-03 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
DE3440138A1 (en) * 1983-11-04 1985-05-15 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Process for producing colour images
JPS6198350A (en) * 1984-10-19 1986-05-16 Konishiroku Photo Ind Co Ltd Silver halide color photographic sensitive material

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5411841A (en) * 1993-05-24 1995-05-02 Eastman Kodak Company Photographic elements containing magenta couplers and process for using same
EP0763774A1 (en) * 1995-09-18 1997-03-19 Minnesota Mining And Manufacturing Company Process for preparation of 2-equivalent 4-arylthio-5-pyrazolone magenta couplers
US5646297A (en) * 1995-09-18 1997-07-08 Imation Corp. Process for preparation of 2-equivalent 4-arylthio-5-pyrazolone magenta couplers

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GB9011102D0 (en) 1990-07-04
GB2244053B (en) 1994-01-05

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