US3393071A - Photographic color material and process utilizing 5-pyrazolone color couplers - Google Patents
Photographic color material and process utilizing 5-pyrazolone color couplers Download PDFInfo
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- US3393071A US3393071A US402651A US40265164A US3393071A US 3393071 A US3393071 A US 3393071A US 402651 A US402651 A US 402651A US 40265164 A US40265164 A US 40265164A US 3393071 A US3393071 A US 3393071A
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- color
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- silver halide
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—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
-
- 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
Definitions
- This invention relates to the manufacture of photographic color images.
- a light-sensitive photographic color material comprising a red-sensitized, a green-sensitized and a bluesensitive silver halide emulsion layer wherein on development by means of suitable color couplers, a cyan, a magenta anda'yello'w dye image are formed respectively.
- suitable color couplers for'negative andpositive materials e.g. with respect to theabsorption spectrum of the dyes to be formed.
- Another object of this invention is to provide photographic processing baths and photographic materials containingfifromS jto' carbon atoms, e.g. an n-octadecyl ra cah' nd' R represents anguns ubstitu'tedarylgroup, e.g.
- a phenyl .group' or 'a substituted jaryl group eg an alkyl-substitute'd phenyl Tg'roup, 1am; alkoxy-substit-uted phenyl 1 gr'onp ,a phenyloxy-subsjtituted,phenyl group, a halogensubstituted phenyl group, an alkylsulfonyl-substituted phenyl group, an arylsul' fony bstituted phenyl group,
- color couplers can be prepared according to a method described in the U.S. patent application Ser. No. 314,594
- the said color couplers do not contain a radical rendering the molecule fast to diffusion; they can be used in the developing solution. Preferably, however, they are incorporated in a non-migratory form into a light-sensitive silver halide emulsion layer or a non-light-sensitive waterpermeable colloid layer, which is in direct contact with'a light-sensitive layer or which is separated from it by a water-permeable layer.
- the color couplers used according to this invention are preferably rendered fast to diffusion by the introductionintheir molecule of an acyclic aliphatic radical containing of from 5 to 20 carbon atoms in straight line.
- New non-diffusing color couplers which according to the present invention are preferably incorporated into the photographic material, have the following structure:
- color couplers may alsofbe incorporated in a silver halide emulsion layer according to themethods of Mannes and Godowsky, U.S. patent specification 2,304,940 and of Jelley and Vittum, US. patent specification 2,322 027.
- the coupler is first dissolved in a water-insoluble high-boiling organic crystalloidal material such as,1,2 -dimethoxybenzene or dimethyl phthalate, and the solution is then dispersed in the silver halide emulsion.
- the 2 -pyrazolin-5-one color couplers used in the present invention are dissolved in a Water-miscible solvent such as ethanol and homogeneously mixedwith the lightsensitive silver halide emulsion during the preparation of the latter.
- the silver halide emulsion normally contains the usual colloids such as gelatin, poly(vinyl alcohol), collodion or other natural or synthetic colloids suitabl therefor.
- the magenta-forming color coupler usually is added to the green-sensitized silver halide emulsion. According to a preferred embodiment this silver halide emulsion is applied as a second color coupler containing layer of a photographic multilayer color material.
- Such multilayer material usually comprises the f-ollowinglayers in the indicated sequence: a support, a red-sensitized silver halide emulsion layer containing a cyan-forming color coupler, a green-sensitized silver halide emulsion layer containing a magenta-forming color coupler, a yellow filter layer mostly consisting of gelatin containing dispersed colloidal silver, and a blue-sensitive silver halide emuslion layer containing a yellow-forming color coupler.
- any color-forming developer containing a primary amino group may be used.
- These include'developers having two primary amino groupsas well as those having one of the amino groups substituted.ohhaving sub's'tituents in the ring such as alkylphenylen'ei-diamines, These .compounds are usually used in the salt form such a s the hydrochloride or the sulfate, which are more. stable than the amines themselves. All of these compoundsh ve an unsubstituted amino group, which enables the oxidation p'roducts of the developer to couple with the color-forming compounds to form a dye.
- Suitable developing substances are aromatic primary amino compounds such as p-phenylenediamine and derivatives thereof such as N,N-diethyl-N -sulfomethyl-p-phenylenediamine and N,N-diethyl- N-carboxymethyl-p-phenylenediamine. f
- One of v the advantages. of the couplers usedaccording to our invention is l thatjthe' dyes formed by coupling with an oxidized developing compound e.g'. N,N-diethyl-pphenylenediamine have an absorption curve with a'very steep slope on the side of the long wave-lengths and with a very high transmission in the blue region of the visible spectrum.
- an oxidized developing compound e.g'. N,N-diethyl-pphenylenediamine
- FIGURE 1 represents the absorption curves A and B of the dyestuffs that are formed by development with N,N-diethyl-p-phenylenediamine of the color couplers having respectively the followingstructural formulas:
- the photographic material After exposure with green light through a grey wedge, the photographic material is developed for 7.5 'min'fat 20C. in a color-developing bath of the following composition:
- Example 2 A similar silver halide emulsion as described in Example 1, wherein the color coupler is replaced by a same amount of the color coupler having the structural Formula 2 dissolved in a mixture of ml. of 0.5 N sodium hydroxide, 80 ml. of isopropanol and 80 ml. of distilled water. After the addition of the usual additives such as hardeners, wetting agents, stabilizers and the necessary amount of distilled water to obtain 1 kg. of emulsion, the latter is coated onto a cellulose triacetate support and dried. After exposure and further processing as described in Example 1, a magenta colored image is obtained having an absorption maximum of 5 30 m Example 3 To /2 kg. of a green-sensitive silver halide emulsion containing 0.0950 mol of silver chloride are added 10 g. of the color coupler having the structural Formula 4, dissolved in a mixture of 40 ml. of 1 N sodium hydroxide,
- the multilayer photographic material consists in the in.- dicated sequence of an antihalation layer, asupport, a gelatin subbing layer, a red-sensitive silver halide emulsion layer containing .acyan-forming color coupler, a gelatin interlayer, a, layer of a green-sensitive silver halide emulsion. prepared as described above, a yellow filterlayer, a blue-sensitive silver halide emulsion layer containing a yellow-forming color coupler, and at least one gelatin overcoat as antistress layer.
- the multilayer color material is exposed through a color negative and further processed as described in Example 1. A positive color image is obtained.
- a method of producing a magenta colored photographic image in a silver halide emulsion layer which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a coupler compound having the following general formula:
- R is an alkyl radical containing from 4 to 20 carbon atoms, and R is an aryl radical.
- a method of producing a magenta colored photo graphic image in a silver halide emulsion layer which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a coupler compound having the following general formula:
- R is a higher alkyl radical containing from 5 to 20 carbon atoms, and R is an aryl radical.
- a method of producing a magenta colored photographic image in a silver halide emulsion layer which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a conpler compound having the following general formula:
- R' is a lower alkyl radical, and R' is an aryl d v i s a, v
- Acolor-forming photographic developer comprising a primary aromatic amino'developing agent andaj coupler compound having the following general formula'z" I H2o 'o-'Nn o0NHa',', v in which R" is a lower alkylradical, and R' is a phenyl radical.
- a photographic emulsion for. preparing a photographic element for formingc-olored images comprising a water-permeable colloid as carrier for light-sensitive silver halide and a color coupler having the general formula:
- a photographic element containing at least one silver halide emulsion layer and containing in non-migratory form a coupler compound having the following general formula: v
- R is an alkyl radical containing from 4 to 20 carbon atoms, and R is an aryl radical.
- a photographic element containing at least one silver halide emulsion layer which contains a coupler compound having the following general formula:
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- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
y 1963 M. J. MONBALIU ET AL 3,393,071
PHOTOGRAPHIC COLOR MATERIAL AND PROCESS UTILIZING -PYRAZOLONE COLOR COUPLERS Filed Oct. 8, 1964 2 Sheets-Sheet 1 ATTORNEYS y 1 1968 M. J. MONBALlU ET AL 3,393,071
PHOTOGRAPHIC COLOR MATERIAL AND PROCESS UTILIZING S-PYRAZOLONB COLOR COUPLERS Filed Oct. 8, 1964 2 Sheets-Sheet I I I I 6 600 W4 ralrgfln 49274112704;
\Q N a x g Qfi INVENTOR-S Wig/ W A. u: flazzalz'w 571 5 a a I e ATTORNEY6 United States Patent ABSTRACT or THE DISCLOSURE S-pyrazolone color couplers having a urea linkage in combination with an alkyl group at the 3 position are described. The color couplers of the invention possess favorable spectral properties for use in positive and reversal color materials.
This invention relates to the manufacture of photographic color images.
The present application is a-continuation-in-part of our application Ser. No. 314,807, filed Oct. 8, 1963, now abandoned. I
It is known that for the manufacture of a photographic color image in a light-sensitive silver halide emulsion layer the exposed silver halide is developed to a silver image by means of an aromatic primary amino compound in the" presence of'a color coupler which by reaction with the oxidized developing substances forms a dye on the areas corresponding with the silver image.
'In the subtractive three-color photography mostly a light-sensitive photographic color material is used comprising a red-sensitized, a green-sensitized and a bluesensitive silver halide emulsion layer wherein on development by means of suitable color couplers, a cyan, a magenta anda'yello'w dye image are formed respectively. As known, distinction should be made between color couplers for'negative andpositive materials e.g. with respect to theabsorption spectrum of the dyes to be formed.
It is an object of the present invention to provide a method for the manufacture of photographic color images by means of color couplers which on color development with an aromatic primary amine as adeveloping substance form a magenta dye possessing favorable spectral properties for'use in' positive and reversal color material.
- "Another object of this invention is to provide photographic processing baths and photographic materials containingfifromS jto' carbon atoms, e.g. an n-octadecyl ra cah' nd' R represents anguns ubstitu'tedarylgroup, e.g. a phenyl .group' or 'a substituted jaryl group, eg an alkyl-substitute'd phenyl Tg'roup, 1am; alkoxy-substit-uted phenyl 1 gr'onp ,a phenyloxy-subsjtituted,phenyl group, a halogensubstituted phenyl group, an alkylsulfonyl-substituted phenyl group, an arylsul' fony bstituted phenyl group,
a sulfamyl group and an N-substit uted sulfamylphenyl p- These color couplers can be prepared according to a method described in the U.S. patent application Ser. No. 314,594
When the said color couplers do not contain a radical rendering the molecule fast to diffusion; they can be used in the developing solution. Preferably, however, they are incorporated in a non-migratory form into a light-sensitive silver halide emulsion layer or a non-light-sensitive waterpermeable colloid layer, which is in direct contact with'a light-sensitive layer or which is separated from it by a water-permeable layer. The color couplers used according to this invention are preferably rendered fast to diffusion by the introductionintheir molecule of an acyclic aliphatic radical containing of from 5 to 20 carbon atoms in straight line.
New non-diffusing color couplers, which according to the present invention are preferably incorporated into the photographic material, have the following structure:
These color couplers may alsofbe incorporated in a silver halide emulsion layer according to themethods of Mannes and Godowsky, U.S. patent specification 2,304,940 and of Jelley and Vittum, US. patent specification 2,322 027. In the process of the latter patent specification the coupler is first dissolved in a water-insoluble high-boiling organic crystalloidal material such as,1,2 -dimethoxybenzene or dimethyl phthalate, and the solution is then dispersed in the silver halide emulsion.
According to a preferred embodiment for. the manufacture of a light-sensitive color material according to the present invention, the 2 -pyrazolin-5-one color couplers used in the present invention,.which are rendered fast. to diffusion by the introduction of a long aliphatic chain in their molecule, are dissolved in a Water-miscible solvent such as ethanol and homogeneously mixedwith the lightsensitive silver halide emulsion during the preparation of the latter. The silver halide emulsion normally contains the usual colloids such as gelatin, poly(vinyl alcohol), collodion or other natural or synthetic colloids suitabl therefor. V
The magenta-forming color coupler usually is added to the green-sensitized silver halide emulsion. According to a preferred embodiment this silver halide emulsion is applied as a second color coupler containing layer of a photographic multilayer color material. Such multilayer material usually comprises the f-ollowinglayers in the indicated sequence: a support, a red-sensitized silver halide emulsion layer containing a cyan-forming color coupler, a green-sensitized silver halide emulsion layer containing a magenta-forming color coupler, a yellow filter layer mostly consisting of gelatin containing dispersed colloidal silver, and a blue-sensitive silver halide emuslion layer containing a yellow-forming color coupler.
In the development of exposed photographic silver halide emulsion layers, using the-couplers described above, any color-forming developer containing a primary amino group may be used. These include'developers having two primary amino groupsas well as those having one of the amino groups substituted.ohhaving sub's'tituents in the ring such as alkylphenylen'ei-diamines, These .compounds are usually used in the salt form such a s the hydrochloride or the sulfate, which are more. stable than the amines themselves. All of these compoundsh ve an unsubstituted amino group, which enables the oxidation p'roducts of the developer to couple with the color-forming compounds to form a dye.
Suitable developing substances are aromatic primary amino compounds such as p-phenylenediamine and derivatives thereof such as N,N-diethyl-N -sulfomethyl-p-phenylenediamine and N,N-diethyl- N-carboxymethyl-p-phenylenediamine. f
,One of v the advantages. of the couplers usedaccording to our invention is l thatjthe' dyes formed by coupling with an oxidized developing compound e.g'. N,N-diethyl-pphenylenediamine have an absorption curve with a'very steep slope on the side of the long wave-lengths and with a very high transmission in the blue region of the visible spectrum.
The absorption curves represented in the accompanying drawings demonstrate clearly the favorable low transmission in theblue and the steep slope of the absorption curves of dyes obtained by means of color couplers used according to the present invention in respect ofthe transmission and the slope of'the absorption curves of dyes obtained with color couplers of a type described in 'U.S. patentspecification 2 ,369,489.
FIGURE 1 represents the absorption curves A and B of the dyestuffs that are formed by development with N,N-diethyl-p-phenylenediamine of the color couplers having respectively the followingstructural formulas:
The following examples illustrate the invention.
"Example! To /2. kg. of a green-sensitive silver halide'emulsion containing 0.0950 mol of. silver chloride are added'lO g. of the color coupler having the structural Formula 4 dis.- solved ina mixture of 40 ml. of l N sodium hydroxide, ml. of isopropanol and 32 ml. of distilled w'aterQAfter addition of the usual additives such as hardeners, wetting agents, stabilizers and the necessary amount of distilled water-to obtain-1 kg. of emulsion,fit'he latter is coated onto a cellulose triacetate support and dried.
After exposure with green light through a grey wedge, the photographic material is developed for 7.5 'min'fat 20C. in a color-developing bath of the following composition:
N,N-diethyl-p-phenylenedia-mine hydrochloride g 3 Sodium hexametaphosphate g 1 Hydroxylamine hydrochloride g 1.2 Anhydrous sodium sulfite g 4 Anhydrous sodium carbonate g 50 Potassium bromide g.. 2.5 Water up to ml 1000 The developed material is rinsed with water for 30 sec. at 18 C. and fixed for 4 min. at 20 C. in a fixing bath of the following composition:
Next, the material is rinsed again for 6 min. at 18 C. and treated for 4 min. in a bleaching bath of the following composition:
Water up to ml '1000 After bleaching, the material is rinsed for 4 min. at 18 C. and fixed again in the fixing bath composed as described above. After a further rinsing for 6 min. at 18 C. the material is stabilized in the following stabilizing bath:
Anhydrous sodium carbonate g 10 Disodiu-m salt of ethylenediamine tetraacetic acid g 2 Paraformaldehyde g 5 Water up to ml 1000 A magenta wedge-image having an absorption maximum at 525 m is obtained.
Example 2 A similar silver halide emulsion as described in Example 1, wherein the color coupler is replaced by a same amount of the color coupler having the structural Formula 2 dissolved in a mixture of ml. of 0.5 N sodium hydroxide, 80 ml. of isopropanol and 80 ml. of distilled water. After the addition of the usual additives such as hardeners, wetting agents, stabilizers and the necessary amount of distilled water to obtain 1 kg. of emulsion, the latter is coated onto a cellulose triacetate support and dried. After exposure and further processing as described in Example 1, a magenta colored image is obtained having an absorption maximum of 5 30 m Example 3 To /2 kg. of a green-sensitive silver halide emulsion containing 0.0950 mol of silver chloride are added 10 g. of the color coupler having the structural Formula 4, dissolved in a mixture of 40 ml. of 1 N sodium hydroxide,
32 ml. of isopropanol and 32 ml. of distilled water. After addition of the usnal-additives such as hardeners, wetting agents, stabilizers and the necessary amount of distilled water to obtain 1 kg. of emulsion, the latter is coated to form part of a multilayer photographic color material. The multilayer photographic material consists in the in.- dicated sequence of an antihalation layer, asupport, a gelatin subbing layer, a red-sensitive silver halide emulsion layer containing .acyan-forming color coupler, a gelatin interlayer, a, layer of a green-sensitive silver halide emulsion. prepared as described above, a yellow filterlayer, a blue-sensitive silver halide emulsion layer containing a yellow-forming color coupler, and at least one gelatin overcoat as antistress layer.
The multilayer color material is exposed through a color negative and further processed as described in Example 1. A positive color image is obtained.
We claim:
1. A method of producing a magenta colored photographic image in a silver halide emulsion layer,'which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a coupler compound having the following general formula:
in which R is an alkyl radical containing from 4 to 20 carbon atoms, and R is an aryl radical. 1
2. A method of producing a magenta colored photo graphic image in a silver halide emulsion layer, which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a coupler compound having the following general formula:
RI I
in which R is a higher alkyl radical containing from 5 to 20 carbon atoms, and R is an aryl radical.
3. A method of producing a magenta colored photographic image in a silver halide emulsion layer, which comprises exposing the layer and developing the layer with an aromatic primary amine in the presence of a conpler compound having the following general formula:
in which R' is a lower alkyl radical, and R' is an aryl d v i s a, v
' 5. "Acolor-forming photographic developer comprising a primary aromatic amino'developing agent andaj coupler compound having the following general formula'z" I H2o 'o-'Nn o0NHa',', v in which R" is a lower alkylradical, and R' is a phenyl radical. v
6. A photographic emulsion for. preparing a photographic element for formingc-olored images comprising a water-permeable colloid as carrier for light-sensitive silver halide and a color coupler having the general formula:
Hi JiI-NHCONH in which R is an alkyl radical containing from 4 to 20 carbon atoms, and R is an aryl radical.
7. A photographic element containing at least one silver halide emulsion layer and containing in non-migratory form a coupler compound having the following general formula: v
in which R is an alkyl radical containing from 4 to 20 carbon atoms, and R is an aryl radical.
8. A photographic element containing at least one silver halide emulsion layer, which contains a coupler compound having the following general formula:
H,( J ii NHooNn -n' p in which R is an alkyll-radical containing was to 20 carbon atoms, and R is an aryl radical.
References Cited UNITED STATES PATENTS 2,369,489 2/1945 Porter et al. 96-100 3,161,512 12/1964 Greenhalgh 96-100 J. TRAVIS BROWN, Primary Examiner.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR990588A FR1417371A (en) | 1963-10-08 | 1964-10-07 | Process for the production of color photographic images and equipment for the production of these images |
CH1299564A CH442985A (en) | 1963-10-08 | 1964-10-07 | Method for obtaining color photographic images |
DEG41721A DE1272718B (en) | 1963-10-08 | 1964-10-07 | Process for producing a purple photographic image |
US402651A US3393071A (en) | 1963-10-08 | 1964-10-08 | Photographic color material and process utilizing 5-pyrazolone color couplers |
BE654109D BE654109A (en) | 1963-10-08 | 1964-10-08 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US31480763A | 1963-10-08 | 1963-10-08 | |
US402651A US3393071A (en) | 1963-10-08 | 1964-10-08 | Photographic color material and process utilizing 5-pyrazolone color couplers |
Publications (1)
Publication Number | Publication Date |
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US3393071A true US3393071A (en) | 1968-07-16 |
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ID=26979557
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Application Number | Title | Priority Date | Filing Date |
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US402651A Expired - Lifetime US3393071A (en) | 1963-10-08 | 1964-10-08 | Photographic color material and process utilizing 5-pyrazolone color couplers |
Country Status (4)
Country | Link |
---|---|
US (1) | US3393071A (en) |
BE (1) | BE654109A (en) |
CH (1) | CH442985A (en) |
DE (1) | DE1272718B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3486894A (en) * | 1966-03-23 | 1969-12-30 | Ferrania Spa | Color photographic images utilizing ureido indazolone couplers |
US3861923A (en) * | 1972-05-31 | 1975-01-21 | Fuji Photo Film Co Ltd | Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound |
FR2336711A1 (en) * | 1975-12-26 | 1977-07-22 | Konishiroku Photo Ind | PROCESS FOR FORMING A MAGENTA COLOR IMAGE |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2369489A (en) * | 1941-09-25 | 1945-02-13 | Eastman Kodak Co | Acylated amino pyrazolone couplers |
US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1147483B (en) * | 1961-09-28 | 1963-04-18 | Ferrania Spa | Multilayer photographic material with color components for color development and process for its manufacture |
-
1964
- 1964-10-07 DE DEG41721A patent/DE1272718B/en active Pending
- 1964-10-07 CH CH1299564A patent/CH442985A/en unknown
- 1964-10-08 BE BE654109D patent/BE654109A/xx unknown
- 1964-10-08 US US402651A patent/US3393071A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2369489A (en) * | 1941-09-25 | 1945-02-13 | Eastman Kodak Co | Acylated amino pyrazolone couplers |
US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3486894A (en) * | 1966-03-23 | 1969-12-30 | Ferrania Spa | Color photographic images utilizing ureido indazolone couplers |
US3861923A (en) * | 1972-05-31 | 1975-01-21 | Fuji Photo Film Co Ltd | Silver halide color photographic materials containing a 3-ureido-5-pyrazolone coupler and an aldehyde compound |
FR2336711A1 (en) * | 1975-12-26 | 1977-07-22 | Konishiroku Photo Ind | PROCESS FOR FORMING A MAGENTA COLOR IMAGE |
Also Published As
Publication number | Publication date |
---|---|
DE1272718B (en) | 1968-07-11 |
BE654109A (en) | 1965-04-08 |
CH442985A (en) | 1967-08-31 |
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