US3861923A - Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound - Google Patents

Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound Download PDF

Info

Publication number
US3861923A
US3861923A US365678A US36567873A US3861923A US 3861923 A US3861923 A US 3861923A US 365678 A US365678 A US 365678A US 36567873 A US36567873 A US 36567873A US 3861923 A US3861923 A US 3861923A
Authority
US
United States
Prior art keywords
color photographic
photographic material
set forth
group
silver halide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US365678A
Other languages
English (en)
Inventor
Hiroshi Hara
Yukio Yokota
Hiroyuki Amano
Tokio Nishimura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3861923A publication Critical patent/US3861923A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39232—Organic compounds with an oxygen-containing function

Definitions

  • the present invention relates to color photography, more particularly, it relates to a color photographic material capable of forming magenta dye images of good heat and moisture resistance.
  • magenta dye images are ordinarily unstable to heat and moisture, and when they are exposed to heat or moisture or are stored for a long period of time, the low density portions of the magenta dye images tend to fade. It is known that such a phenomenon occurs due to unreacted coupler remaining in the color photographic material, and, thus, the aforesaid tendency is particularly seen at low density image portions where a large amount of unreacted coupler remains (see, e.g., P. W. Vittum; Journal of the American Chemical Society; Vol. 72, 1533(1950)).
  • a bispyrazolone prepared by the condensation of 3-acylamino-5- pyrazolone and an aldehyde is used as the magenta coupler.
  • a bispyrazolone has the fault that it does not give a sufficient coupling density upon color development.
  • the dye image formed by such a bispyrazolone is not very fast to heat and moisture.
  • One object of this invention is, therefore, to provide a color photographic material capable of forming fast magenta images.
  • non-diffusible in this specification has its well known meaning as it is used for color couplers in the field of color photography, i.e., it means that the coupler does not substantially move in the colloid layers of a photographic material in the presence of an aqueous alkaline processing solution.
  • R represents an alkyl group
  • most generally the alkyl group will have 1 to 32 carbon atoms, though this range is not limitative. It is most preferred that when R, is an alkyl group it have 8 to 18 carbon atoms, since an alkyl group with 8 or more carbon atoms acts as a ballasting group, while alkyl groups of 19 or more carbon atoms are not preferred from an industrial stand point, i.e., the compounds have an increased production cost, difficulty of synthesis, etc.
  • R is an aryl group, it is monoaryl as exemplified in the following paragraphs.
  • R represents a substituted phenyl group
  • preferred substituents include halogen, cyano, nitro, alkyl of 1-18 carbon atoms, alkoxy of l-l8 carbon atoms, aryl, e.g., phenyl, tolyl, etc., aryloxy, e.g., phenoxy, etc., carbamoyl, sulphamoyl, sulphonamido or acyl.
  • R examples include phenyl, 2- chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl, 2,6- dichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3,5-dibromophenyl, 2-cyanophenyl, 3-nitrophenyl, 4- methylphenyl, 2,6-dimethylphenyl, 2,6-diethylphenyl, 4-butylphenyl, 2-trifluoromethylphenyl, 2- ethoxyphenyl, 4-phenylphenyl, 4-phenoxyphenyl, N- methylbenzamidophenyl, N,N-diphenylcarbamoylphenyl, N,N-dibutylsulfamoylphenyl, N,N-diphenylsulfamoylphenyl, N-methylsulfonamidophenyl, Z-methyl- 5-nitrophenyl, 2-ch
  • the couplers of the formula in which at least one orthoposition of the phenyl group represented-by R has been substituted by a halogen atom, an alkyl group having l-5 carbon atoms, or an alkoxyl group having 1-5 carbon atoms is particularly preferred.
  • R R R R R R R and R H R each represents an alkyl group; R R and R each rep- 5 resents a hydrogen atom or an alkyl group; and n is an integer of 1-5.
  • any alkyl group for the moi- R 5 eties R to R listed above will have from 1 to 18 car- -NHCO CH bon atoms, and for practical purposes are preferably I unsubstituted.
  • ballast groups are hydrophobic groups usually containing 8 to 32 carbon atoms.
  • the 3-ureido-5pyrazolor e couplers used in this in.- vention can be prepared according to the methods described in US. Pat. No. 3,558,319; and Japanese Patent Applications 100911/1970; 106716/1970, etc.
  • the abovementioned 3-ureido-5-pyrazolone couplers can be used alone or as a combination of two or more couplers.
  • the 3-ureido-5-pyrazolor e coupler may be used together with other two-equivalent or four-equivalent couplers.
  • These couplers are sometimes called colorless couplers, colored couplers or DlR couplers, and specific examples of them include the couplers described in US. Pat. Nos. 2,455,170; 2,600;7,88; 2,908,573; 3,062,653; 3,148,062;
  • the 3-ureido-5-pyrazolene couplers of the present invention are not particularly limited in proportions so long as the objects of the present invention are met. However, generally speaking, they will be used in an amount of from about to about 100 percent by weight, preferably 50 to 100 percent by weight, of the total amount of magenta color forming couplers used.
  • Those color couplers are introduced into a hydrophilic colloid as is typically used for photographic materials according to any known method. For instance, they can be dispersed in a hydrophilic colloid using a high boiling point organic solvent such as dibutyl phthalate and tricresyl phosphate as described in U.S. Pat. No. 2,322,027 and/or a low-boiling point organic solvent such as ethyl acetate and tetrahydrofuran as described in U.S. Pat. Nos. 2,801,170; 2,801,171; and 2,946,360.
  • a high boiling point organic solvent such as dibutyl phthalate and tricresyl phosphate as described in U.S. Pat. No. 2,322,027
  • a low-boiling point organic solvent such as ethyl acetate and tetrahydrofuran as described in U.S. Pat. Nos. 2,801,170; 2,801,171; and 2,
  • the aldehydes used together with the 3-ureido-5- pyrazolone coupler according to the present invention include compounds having an alkyl group, an aryl group, or a heterocyclic group bonded to the aldehyde group, i.e., aliphatic aldehydes, aromatic aldehydes or heterocyclic aldehydes can be used in the present invention.
  • the aliphatic aldehydes preferably contain from 2 to 20 carbon atoms, most preferably 2 to 8 carbon atoms.
  • aromatic aldehydes most preferred are those containing a formyl group attached to the phenyl or naphthyl ring, though aryl substituted with halogen, nitro, hydroxy, C -C alkyl, C,C alkoxy ally], carboxy, sulpho and the like are also useful.
  • aldehydes benzaldehydes with or without the above substituents are preferred.
  • Such compounds are acetaldehyde, propionaldehyde, butylaldehyde, isobutylaldehyde, pivalylaldehyde, heptaldehyde, laurin aldehyde, stearinaldehyde, succindialdehyde, crotonaldehyde, benzaldehyde, o-chlorobenzaldehyde, mchlorobenzaldehyde, p-chlorobenzaldehyde, pbromobenzaldehyde, p-nitrobenzaldehyde, p-
  • aldehydes can be used alone or as a combination of two or more of such aldehydes.
  • the addition amount of the aldehyde is usually about 0.05 to about mols, in particular about 0.1 mol to about 10 mols, per mol of the coupler.
  • the aldehyde be added to a hydrophilic colloid when preparing the coupler dispersion by adding the abovedescribed coupler or couplers to the hydrophilic colloid together with the aforesaid high boiling point organic solvent and/or the low boiling point organic solvent.
  • they can be added to a silver halide emulsion at the preparation of coating compositions together with the coupler dispersion, a hardening agent, a stabilizer, a wetting agent, etc.
  • the amount of magenta forming coupler in accordance with the present invention is not limited so long as, of course, the color photographic material of the present invention meets the objects heretofore recited, that is, yields a magenta dye image of good heat and moisture resistance.
  • the amount of magenta color forming coupler will be from about 0.05 to about 0.5 moles per mole of silver halide, most preferably, 0.07 to 0.2 moles per mole of silver halide.
  • hydrophilic colloid(s) as are used in the color photographic art can be used as the hydrophilic colloid for the silver halide photographic emulsion layer of this invention.
  • hydrophilic colloids are gelatin, albumin, gum arabic. agar agar, cellulose derivatives (such as alkyl esters of carboxymethyl cellulose, hydroxyethyl cellulose, carboxymethyl hydroxyethyl cellulose, etc.), and synthetic resins (such as polyvinyl alcohol, polyvinyl pyrrolidone, etc.).
  • hydrophilic colloids are also preferably used as the binders for layers of the photographic material other than the silver halide emulsion layers, such as a protective layer, a filter layer, an intermediate layer, an antihalation layer, a subbing layer, a backing layer, etc.
  • hydrophilic colloids used in various layers of the photographic material of this invention can be effectively hardened by hardening agents such as 1,4- dioxanes, aziridines, iso-oxazoles, active halogens, active vinyl compounds, etc. Typical examples of such hardening agents are described in U.S. Pat. Nos.
  • any silver halide emulsion as is usually used in the field of photography such as a silver bromide emulsion, silver iodobromide emulsion, silver chloroiodobromide emulsion, silver chlorobromide emulsion and silver chloride emulsion can be used.
  • the so-called converted halide type silver halide emulsions as described in, e.g., U.S. Pat. No. 3,622,318 and British Pat. No. 635,841 can be used.
  • a preferred average gain size for the silver halide is from about 0.05 to about 1.5 microns.
  • the weight ratio of silver halide to binder most suitably ranges from about 0.2 to about 20 (silver halide/binder), preferably about 0.3 to about 5 in the layer. These values are not limitative, but provide a most superior element.
  • the silver halide emulsions (used in the color photographic materials) of this invention can be chemically sensitized by active gelatin or a sulfur compound according to the process described in U.S. Pat. Nos. 1,574,944; 1,623,499 and 2,410,869. They can also be sensitized by a noble metal salt such as a palladium or a gold salt as described in U.S. Pat. Nos. 2,448,060; 2,399,083 and 2,642,361. Furthermore, they can be sensitized by a reducing agent such as a stannous salt as described in U.S. Pat. No. 2,487,850, or sensitized by a polyalkylene derivative.
  • the silver halide emulsion of this invention can contain a stabilizer such as a mercury compound, mercaptotetrazole, thiazole, azaindene, etc.; a plasticizer such as glycerin, latex, etc.; and a wetting agent such as saponin, polyethylene glycol monolauryl ether, etc.
  • a stabilizer such as a mercury compound, mercaptotetrazole, thiazole, azaindene, etc.
  • a plasticizer such as glycerin, latex, etc.
  • a wetting agent such as saponin, polyethylene glycol monolauryl ether, etc.
  • the silver halide emulsion can contain an antistatic agent, an ultraviolet absorbent, a fluorescent whitening agent, dyes, etc.
  • the silver halide emulsion containing the 3-ureido-5- pyrazolone and the aldehyde compound according to this invention is effectively used as a green-sensitive emulsion layer in an ordinary multi-layer color photographic material.
  • the order of the photosensitive emulsion layers may be, from the support side, a red-sensitive emulsion layer, a green-sensitive emulsion layer and a blue-sensitive emulsion layer, or may be a blue-sensitive emulsion layer, red-sensitive emulsion layer and a green-sensitive emulsion layer.
  • the color photographic material of this invention can have an antihalation layer, intermediate layer(s), filter layer, protective layer, etc.
  • the support for the photographic materials of this invention on which the photosensitive silver halide emulsion layers are formed is preferably a cellulose ester film such as a cellulose nitrate film, a cellulose acetate film, etc.; a polyester film such as a polyethylene terephthalate film; a polyvinyl chloride film; a polystyrene film; a polycarbonate film; a baryta-coated paper; a resin-coated paper, and the like.
  • This listing is, of course, not limitative.
  • the color photographic material of this invention is imagewise exposed in an ordinary way and then processed according to usual color photographic processings.
  • the main processing steps are a color development, a bleach and a fix and, if necessary, a washing step may be applied between each step.
  • After fixing the color photographic material is washed and dried but it is desirable to process the color photographic material in a stabilization bath prior to drying.
  • photographic processing temperatures typically range from about C or less to 60C or higher. Temperatures of about 30C or higher are suitable for high speed processing procedures. Processing times for each processing step can vary widely, depending on the processing temperature, but usually range from several seconds to several minutes or more.
  • Useful color developers are aqueous alkaline solutions containing a color developing agent.
  • a color developing agent all known primary aromatic amine dye-forming developing agents can be used.
  • color developing agents are phenylenediamines such as N,N-diethyl p-phenylenediamine, N-ethylhydroxyethyl p-phenylenediamine, N-ethyl-N- hydroxyethyl-2-methyl p-phenylenediamine, N-ethyl- B-N-methane sulfoneamidoethyl-3-methyl-4- aminoaniline, N,N-diethyl-2-methyl-pphenylenediamine, and sulfates, hydrochlorides, sulfides, etc., thereof.
  • the color developer used for developing the color photographic material of this invention may further contain ordinary additives as are used in this art such as a sulfite of an alkali metal, a carbonate, a bisulfite, a bromide, an iodide, benzyl alcohol, etc.
  • the bleach solution can contain any known bleaching agent such as ferricyanide, bichromate, etc.
  • the fix solution can contain any known fixing agent such as sodium thiosulfate, potassium thiocyanate, etc.
  • the bleach step and the fix step can be conducted in one bath, and such a blix bath is described in, e.g., U.S. Pat. No. 3,582,322.
  • Typical bleach agents are discussed in detail in the Journal of the Society of Motion Picture and Television Engineers 61, 667-701 and U.S. Pat. No. 3,189,452; typical fix agents in Mason, Photographic Processing Chemistry, pages 187-188, Focal Press (1966); and typical blix solutions in German Pat. Nos. 866,605 and 966,410, in British Journal of Photography, pages 122123 and 126 (1966) and in U.S. Pat. No. 3,582,322. These references also discloses generally used proportions.
  • the photographic material of this invention provides stable color images which are not faded if the photographic material is exposed to heat or moisture or stored for a long period of time.
  • This merit is obtained by the combination of the 3-ureido-5-pyrazolonc and the aldehyde as mentioned above without using formulin, i.e., since the aldehydes of the present invention are limited to those having an aldehyde group bonded to a carbon atom, formaldehyde is excluded from the scope of the present invention. This is quite astonishing upon considering that if the aforesaid aldehyde is used together with 3-acylamino-5-pyrazolone, the stability of the color images cannot be improved.
  • the aldehyde used in this invention does not have a harmful influence on the photographic properties, e.g., hindering the coupling of couplers and causing stain as in the case of using formalin or a compound releasing formalin.
  • the aldehyde in this invention has the effect of preventing the formation of magenta development fog. Further, changes in sensitivity of the photosensitive emulsion of this invention during storage is prevented. This effect is further observed in the emulsion layers formed over or under the silver halide emulsion layer of this invention, and is a surprisingly effect.
  • Coupler dispersion A B C D Coupler l g 100 g 100 g (earlier set out) Coupler A (known) 100 g Dibutyl phthalate 100 g 100 g I00 g 100 g Ethyl acetate 200 g 200 g 200 g 200 g 10% aqueous gelatin 1000 g 1000 g 1000 g 1000 g solution Aqueous solution of 50 g 50 g 50 g 50 g 5% sodium dodecylbenzene sulfonate Acetaldehyde 6 g Heptaldehyde 5 g Known coupler A: the condensation product of 1- phenyl-3-[3-(2-carboxymethyleicos-3-enamide)-benzamido]-5-pyrazolone and acetaldehyde described in U.S. Pat. No. 3,468,666.
  • Sample D containing the known coupler gave insodium metaborate 25 g sufficient coupling density and gave unstable dye M- sodium sulfite 2 g ages hydroxylamine (sulfate) 2 g potassium bromide 0.5 g 6-nitrobenzimidazole (nitrate) 0.02 g sodium hydroxide 4 g
  • EXAMPLE 2 benzyl alcohol l5.8 ml dNiethhylprltle glycol 20 ml
  • a subbing layer was formed on a cellulose acetate -et y- -B-(methanesulfone- 8 g amidoelhyl) p phenylenediamine fllm support having an antlhalatlon layer contain ng water to make 1000 ml carbon black on the opposlte slde, and then a coating composition containing a silver iodobromide emulsion lron salt of ethylenedlaml
  • Stabilizing bath a blue-sensitive layer.
  • a gelatin intermediate layer was "F acid 10 2; formed on the blue-sensitive layer and a coating comzlnc sulfate 10 g Sodium member 20 g posltlon containing a gelatlno silver chlorobromlde water to make 1000 ml.
  • the perintermediate layer was coated on the red-sensitive layer centage of dye remaining in the portions having image and then a coating composition containing 100 g of sildensities of 0.5 and 1.5 before the fading test were calver chlorobromide (containing 0.06 mol of silver) conculated by the following equation and are shown in taining 35 mol percent bromide and spectrally sensi- Table l. tized so that it had its sensitization maximum at about 555 mg, and 250 g ofa coupler dispersion prepared by Dye rema ng Pe ce tage X 100 dispersing the following components by means of a ho- A.
  • the compositions of the processing solutions used in the steps were as follows:
  • 2-amino-S-diethylaminotoluene hydrochloride (anhydrous) gg I a coupler dispersion prepared by dispersing a sensitizwater 0 ma e m a Colo, developer; mg dye having its sensitization maximum at about 545 Water 800 ml my. and the components shown below by means of a sodium hexametaphosphate 2 g anhydrous Sodium Sulfite 4 g homogenizer was coated in a coated silver amount of l X 10 mol/m 3 g sodium carbonate (monohydrate) 2.5 g potassium bromide 2 0 g water to make 1000 ml Blix solution:
  • a color photographic material which provides magenta dye images of excellent heat and moisture resistance and reduced magenta development for comprising a support having thereon a silver halide photographic emulsion layer containing a 3-ureido-5- pyrazolone magenta coupler and a compound having an aldehyde group bonded to a carbon atom;
  • magenta coupler is a compound represented by the formula wherein R, represents an alkyl group or an aryl group and R represents a phenyl group;
  • aldehyde group is bonded to the carbon atom of an alkyl group, an aryl group or a furfural group, wherein said alkyl group contains from 2-20 carbon atoms and said aromatic group is a formylsubstituted phenyl or naphthyl ring.
  • R is a C,C carbon atom alkyl group or a monoaryl group and R is a phenyl group.
  • R is a C,,C,,, carbon atom alkyl group, a phenyl group or a tolyl group.
  • R is a phenyl group substituted with a halogen atom, a C,C alkyl group or a C,C alkoxyl group.
  • ballast group is a C -C hydrophobic group.
  • tolualdehyde tolualdehyde, cinnamaldehyde, a-naphthaldehyde or furfural.
  • R is a phenyl group selected from:
  • R R R R R R and R each represent an alkyl group, and n is an integer of 1-5.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US365678A 1972-05-31 1973-05-31 Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound Expired - Lifetime US3861923A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP5450072A JPS5535696B2 (enrdf_load_stackoverflow) 1972-05-31 1972-05-31

Publications (1)

Publication Number Publication Date
US3861923A true US3861923A (en) 1975-01-21

Family

ID=12972341

Family Applications (1)

Application Number Title Priority Date Filing Date
US365678A Expired - Lifetime US3861923A (en) 1972-05-31 1973-05-31 Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound

Country Status (4)

Country Link
US (1) US3861923A (enrdf_load_stackoverflow)
JP (1) JPS5535696B2 (enrdf_load_stackoverflow)
DE (1) DE2327731A1 (enrdf_load_stackoverflow)
GB (1) GB1397175A (enrdf_load_stackoverflow)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960571A (en) * 1973-09-27 1976-06-01 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4189321A (en) * 1977-08-31 1980-02-19 Konishiroku Photo Industry Co., Ltd. Process for forming magenta dye images

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5173433A (ja) * 1974-12-23 1976-06-25 Konishiroku Photo Ind Harogenkaginshashinkankozairyo
JPS5914741B2 (ja) * 1975-08-15 1984-04-05 富士写真フイルム株式会社 カラ−写真感光材料

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2518686A (en) * 1945-11-08 1950-08-15 Gen Aniline & Film Corp Aldehyde antistain baths for developed color photographic material
US3140177A (en) * 1960-11-10 1964-07-07 Eastman Kodak Co Processing color photographic materials
US3393071A (en) * 1963-10-08 1968-07-16 Gevaert Photo Prod Nv Photographic color material and process utilizing 5-pyrazolone color couplers
US3468666A (en) * 1966-05-05 1969-09-23 Fuji Photo Film Co Ltd Color photographic silver halide light-sensitive materials containing bis-pyrazolone couplers
US3558319A (en) * 1966-07-13 1971-01-26 Fuji Photo Film Co Ltd Color photographic silver halide emulsion containing magenta couplers

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2518686A (en) * 1945-11-08 1950-08-15 Gen Aniline & Film Corp Aldehyde antistain baths for developed color photographic material
US3140177A (en) * 1960-11-10 1964-07-07 Eastman Kodak Co Processing color photographic materials
US3393071A (en) * 1963-10-08 1968-07-16 Gevaert Photo Prod Nv Photographic color material and process utilizing 5-pyrazolone color couplers
US3468666A (en) * 1966-05-05 1969-09-23 Fuji Photo Film Co Ltd Color photographic silver halide light-sensitive materials containing bis-pyrazolone couplers
US3558319A (en) * 1966-07-13 1971-01-26 Fuji Photo Film Co Ltd Color photographic silver halide emulsion containing magenta couplers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3960571A (en) * 1973-09-27 1976-06-01 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US4189321A (en) * 1977-08-31 1980-02-19 Konishiroku Photo Industry Co., Ltd. Process for forming magenta dye images

Also Published As

Publication number Publication date
JPS4911331A (enrdf_load_stackoverflow) 1974-01-31
DE2327731A1 (de) 1973-12-20
GB1397175A (en) 1975-06-11
JPS5535696B2 (enrdf_load_stackoverflow) 1980-09-16

Similar Documents

Publication Publication Date Title
US3141771A (en) Aldehyde scavengers for photographic silver halide developers
US4009038A (en) Silver halide color photographic materials
US3935016A (en) Silver halide color photographic materials containing 3-anilino-5-pyrazolone couplers
US3128182A (en) Silver halide solvent containing developers and process
JPH0670709B2 (ja) 増加した露出ラチチュードを有する写真プリント材料
US4141730A (en) Multilayer color photographic materials
US5219722A (en) Silver halide color photographic light-sensitive material
CA1246924A (en) Light-sensitive silver halide color photographic material
US3834908A (en) Color silver halide photographic materials containing bis-pyrazolone color couplers
US3861923A (en) Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound
US4306015A (en) Color photographic material
JPH0314168B2 (enrdf_load_stackoverflow)
JP2877579B2 (ja) ハロゲン化銀カラー写真感光材料
US3764327A (en) Color photographic light sensitive material
US3706556A (en) Method for preventing color mixing in multiple layer-type reversal color photographic light-sensitive materials
US5164288A (en) Photographic element containing pyrazoloazole coupler and oxidized developer competitor
US3447926A (en) Color photographic silver halide elements containing 4-substituted urazoles and/or cycloalkane-1,3-diones
JPS6257024B2 (enrdf_load_stackoverflow)
JP2929511B2 (ja) ハロゲン化銀カラー写真感光材料
JPS5942541A (ja) ハロゲン化銀カラ−写真感光材料
GB1601321A (en) Colour photographic material containing benzotriazole derivative
JPS58221844A (ja) カラ−写真感光材料
US3741765A (en) Process for developing silver halide color photographic light-sensitive materials at high temperature
JP2000029179A (ja) ハロゲン化銀感光材料
JPH0216503B2 (enrdf_load_stackoverflow)