US2455169A - Colored couplers - Google Patents
Colored couplers Download PDFInfo
- Publication number
- US2455169A US2455169A US533931A US53393144A US2455169A US 2455169 A US2455169 A US 2455169A US 533931 A US533931 A US 533931A US 53393144 A US53393144 A US 53393144A US 2455169 A US2455169 A US 2455169A
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- US
- United States
- Prior art keywords
- coupler
- developing
- layer
- colored
- compound
- 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
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Classifications
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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
- G03C7/333—Coloured coupling substances, e.g. for the correction of the coloured image
- G03C7/3335—Coloured coupling substances, e.g. for the correction of the coloured image containing an azo chromophore
Definitions
- Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images upon photographic development are Well known. Generally, these color-forming compounds or couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporatedin the emulsion layer and the unused coupler remains after formation of the colored image. When the coupler is used in the developing solution, it ma be colored without detriment to the final image, and some colored couplers are known, such as paraphenylazo acetoacetanilide which wasdisclosed in Mannes an Godowsky Patent 2,108,602.
- the new couplers are, in themselves, more or less strongly colored, and during the coupling reacfurther substituted.
- the aromatic or heterotion the chromophore system in the coupler is broken up with the result that the original color of the coupler is destroyed and a new dye is formed.
- the coupler color is destroyed, and a new color is formed by the coupling reaction, at those points where development occurs. There is formed in this way a dye image of one color on a background of another color.
- an object of the present invention to provide a colored coupler whose chromophore system is destroyed on coupling.
- a further object is to provide a novel radical replacement type of chemical reaction.
- a still further object is to provide color couplers suitable for color corwhere R is an aromatic or heterocyclic radical, especially an aromatic radical of the benzene series. Either the phenol nucleus or the aromatic or heterocyclic radical may contain other substltuents.
- the phenol radical may have a fused-on benzene ring which may be cyclic radical (R in the general formula) may contain substituents; such as alkyl, carboxylic acid, hydroxyl, sulfonic acid, sulfonamide, alkylamine, acylamine or alkoxy.
- the photographic developing solution-or in the emulsion layer according to their intended use and diffusion characteristics.
- Nos. 4, 5, 6-,. and .8 are suitable for use in the'emulsion layer.
- the compounds When. incorporated in the emulsion layer, the compounds may be added directly to their silver halide emulsion as the sodium or other water-soluble salt or they may be incorporated in a coupler solvent as. de
- diazotized solution was added to a solution of 144 g. (01 mole) of a-naphthol in 160 cc. of water which contained g. (0.5 mole) of sodium hydroxide. Ice was added in order to keep the temperature below 5 C. After standing for two hours .at.5 0., the alkaline solution was acidified mine and-para-aminophenol.
- TheI-Ianson process involves a color correction methodin which a colored coupler is incorporated in the photographic emulsion layer prior to exposureand upon development is converted into 'a colored imagewhere the layer was exposed.
- the coupler remaining in the unexposed portions of the layer retains its original color, and by suitable choice of thecolor of the original coupler and the color of the. final dye image, a masking or correction efiect. can be. obtained.
- the primary aromatic amino developing agents are. generally suitable including the phenylenediamines and aminophenols.
- the alkyl phenylenediamines may be substituted in the amino group as well as in the ring.
- Suitable compounds are diethylparaphenylenediamine, monomethyl'paraphenylenediamine, dimethyl paraphenylenedia- These compounds are. usually employed in the salt form, such as the hydrochloride or the sulphate whichare more stable than the free amines. All of' these compounds have a primary amino group which en- ;ables-the oxidation product of' the developer to couplewith'the color-forming compounds to form dye images.
- the following developing solution is suitable for developing gelatino silver halide layers containing; colored couplers according to our invention.
- R is selected from the class consisting of aromatic and heterocyclic radicals
- R is a naphthalene nucleus, said nucleus having the azo group and the hydroxyl para to each other, and R is selected from the class consisting of aromatic and heterocyclic radicals
- said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
- X is selected from the class consisting of hydrogen, hydroxyl, sulfonic acid, sulfonamido, dialkylamino, and acetylamino groups
- said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
- R is selected from class consisting of aromatic and heterocyclic radicals
Description
l atentecl Nov. 30, 194$ COLORED COUPLERS Dudley B. Glass, Paul W. Vittum, and Arnold Weissberger, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application May 3, 1944, Serial No. 533,931
Claims. (Cl. 956) This invention relates to color photography and particularly to coupler compounds for use in photographic processes.
Color-forming compounds which react with the development product of aromatic amino developing agents to form colored images upon photographic development are Well known. Generally, these color-forming compounds or couplers are colorless or substantially colorless. This lack of color is usually desirable where the coupler is to be incorporatedin the emulsion layer and the unused coupler remains after formation of the colored image. When the coupler is used in the developing solution, it ma be colored without detriment to the final image, and some colored couplers are known, such as paraphenylazo acetoacetanilide which wasdisclosed in Mannes an Godowsky Patent 2,108,602.
We have now found a new type of coupler which may have applications in several fields. The new couplers are, in themselves, more or less strongly colored, and during the coupling reacfurther substituted. The aromatic or heterotion, the chromophore system in the coupler is broken up with the result that the original color of the coupler is destroyed and a new dye is formed. Thus, on developing an emulsion layer containing one of these colored couplers, the coupler color is destroyed, and a new color is formed by the coupling reaction, at those points where development occurs. There is formed in this way a dye image of one color on a background of another color.
It is, therefore, an object of the present invention to provide a colored coupler whose chromophore system is destroyed on coupling. A further object is to provide a novel radical replacement type of chemical reaction. A still further object is to provide color couplers suitable for color corwhere R is an aromatic or heterocyclic radical, especially an aromatic radical of the benzene series. Either the phenol nucleus or the aromatic or heterocyclic radical may contain other substltuents. For example, the phenol radical may have a fused-on benzene ring which may be cyclic radical (R in the general formula) may contain substituents; such as alkyl, carboxylic acid, hydroxyl, sulfonic acid, sulfonamide, alkylamine, acylamine or alkoxy.
In previous descriptions of phenolic hydroxyl compounds for color photography, it has been assumed that the position para to the hydroxyl group must be unsubstituted or substituted with certain readily replaceable groups, such as halogen, in order for coupling with the developer to occur. We have found that the position para t0 the phenolic hydroxyl group may be substituted with an azo group and that this group is removable by the oxidized developer when the amsubstituted coupler is treated with the oxidized developer either. in aqueous solution or in the Thus the coupler photographic emulsion layer. may be converted to a coupled compound and the azo groupireadily removed from it by means of reaction with the oxidized] developing agent. This reaction appears to proceed as follows:
where R is the same as in the general formula above.
The following examples illustrate compounds which contain para-azo-substituted phenolic hydro'Xy groups according to the general formulas above and which may be used to produce colored images according to our invention:
4-(X-phenylazo)-l-napl1tliol X=H, OH, SOaH, SOzNHz, N(OH3)2, NH COOHa, OCHa, COOH 5-(5-carbcry-2-isopropyl-plienyl-azo)- S-hydroxyquinoline 4-(X-phenylazo)-5-p-toluene-si11fcnamido)-1- naphthol X=same as Example 1 CHzCHzCH stooges.
X=same as Example 1 2-a-(p-tert.-amylphenoxy) butyramido-4-(p-acetamidophenylazo)phenol HOQ :nO-SOmm NH-C o-on-ootnu z-a-(p tert-amylphenoxyl-butyramido-4g(p-sulfamylphenylazo)-5- C1 methylphenol 7. i
2-chloro-4-(2-bcnzothiazolylazo)-1-naphthol 1 NH to I 05 11 2-(p-tert.-amylbenzoylamino)-4-(Z-qulnolyl-azo)-5-methylphenol Our compounds may be incorporated in the.
photographic developing solution-or in the emulsion layer according to their intended use and diffusion characteristics. In -"the specific examples listed above, Nos. 4, 5, 6-,. and .8 are suitable for use in the'emulsion layer. When. incorporated in the emulsion layer, the compounds may be added directly to their silver halide emulsion as the sodium or other water-soluble salt or they may be incorporated in a coupler solvent as. de
' essary in order to keep the reaction temperature at-.0. 3 C. After standing for ten minutes, the
diazotized solution was added to a solution of 144 g. (01 mole) of a-naphthol in 160 cc. of water which contained g. (0.5 mole) of sodium hydroxide. Ice was added in order to keep the temperature below 5 C. After standing for two hours .at.5 0., the alkaline solution was acidified mine and-para-aminophenol.
witlrS'O cc. of concentrated hydrochloric acid. The azo compound was removed by filtration, washed with water and dried in air. The yield was quantitative. After recrystallizing from acetic acid; the product melted at 239240 0;
Our' compounds are particularly useful in a process, such as that of Hanson U. S. Patent $449,966, granted-September 21, 1948. TheI-Ianson process involves a color correction methodin which a colored coupler is incorporated in the photographic emulsion layer prior to exposureand upon development is converted into 'a colored imagewhere the layer was exposed. The coupler remaining in the unexposed portions of the layer retains its original color, and by suitable choice of thecolor of the original coupler and the color of the. final dye image, a masking or correction efiect. can be. obtained.
Various photographic developing agents can be employed with the couplers of our invention. The primary aromatic amino developing agents are. generally suitable including the phenylenediamines and aminophenols. The alkyl phenylenediamines may be substituted in the amino group as well as in the ring. Suitable compounds are diethylparaphenylenediamine, monomethyl'paraphenylenediamine, dimethyl paraphenylenedia- These compounds are. usually employed in the salt form, such as the hydrochloride or the sulphate whichare more stable than the free amines. All of' these compounds have a primary amino group which en- ;ables-the oxidation product of' the developer to couplewith'the color-forming compounds to form dye images.
The following developing solution is suitable for developing gelatino silver halide layers containing; colored couplers according to our invention.
2-amino-5-diethyl-amino toluene I-ICli ams" 2 Sodium sul'phitedo 2 Sodium carbonate do 20 Potassium bromide. do 2 Water to liter 1 where R isan aromatic nucleus selected from the: class consisting. of. nuclei of the benzene and naphthalene series, said nucleus having the azo' group and the hydroxyl group para to each other,
and R is selected from the class consisting of aromatic and heterocyclic radicals, and said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the --N=N-R group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
2. The method of developing a colored image in a silver halide emulsion layer, which comprises incorporating in said layer a coupler compound having the formula: 1
where R is a naphthalene nucleus, said nucleus having the azo group and the hydroxyl para to each other, and R is selected from the class consisting of aromatic and heterocyclic radicals, and said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
3. The method of developing a colored image in a silver halide emulsion layer, which comprises incorporating in said layer a coupler compound having the formula:
where X is selected from the class consisting of hydrogen, hydroxyl, sulfonic acid, sulfonamido, dialkylamino, and acetylamino groups, and said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
4. The method of developing a colored image in a silver halide emulsion layer, which comprises incorporating in said layer a coupler compound having the formula:
where R is selected from class consisting of aromatic and heterocyclic radicals, and said coupler compound contains no reactive phenolic hydroxyl group other than that to which the azo group is attached, exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the --N=NR group in said coupler'compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
5. The method of developing a colored image in a silver halide emulsion layer, which comprises incorporating in said layer a coupler compound having the formula:
exposing said layer and developing it with a primary aromatic amino developing agent, thereby splitting off the group in said coupler compound and coupling said compound at the point of splitting with the oxidation product of the primary aromatic amino developing agent to form a dye image, leaving said coupler compound intact in the regions of said layer undeveloped by said developing agent.
DUDLEY B. GLASS.
PAUL W. VITTUM.
ARNOLD WEISSBERGER.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,102,028 Fischer June 30, 1914 2,092,425 Ullman et al. Sept. 7, 1937 2,107,941 Hess et a1. Feb. 8, 1938 2,108,602 Mannes et al. Feb. 15, 1938 2,135,366 Tinker Nov. 1, 1938 2,182,814 Marasco Dec. 12, 1939 2,189,817 Morris Feb. 13, 1940 2,220,123 Schwarc Nov. 5, 1940 2,227,981 Schinze1 Jan. 7, 1941 2,263,012 Schinzel Nov. 18, 1941 2,271,230 Peterson et a1 Jan. 27, 1942 2,295,008 Porter et a1. Sept. 8, 1942 2,295,009 Porter et al Sept. 8, 1942 2,297,732 Woodward Oct. 6, 1942 2,299,641 Middleton et a1. Oct. 20, 1942 2,304,820 Hanford et a1. Dec. 15, 1942 2,308,023 Peterson Jan. 12, 1943 2,322,006 Fierke et al June 15, 1943 2,330,291 Kirby Sept. 28, 1943 2,367,531 Salminen Jan. 16, 1945 FOREIGN PATENTS Number Country Date 503,752 Great Britain Apr. 11, 1939 503,824 Great Britain Apr. 11, 1939
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE476360D BE476360A (en) | 1944-05-03 | ||
NL71530D NL71530C (en) | 1944-05-03 | ||
US533931A US2455169A (en) | 1944-05-03 | 1944-05-03 | Colored couplers |
FR950286D FR950286A (en) | 1944-05-03 | 1946-08-29 | New colored couplers |
CH282410D CH282410A (en) | 1944-05-03 | 1947-12-23 | Photosensitive material for color photography. |
CH280513D CH280513A (en) | 1944-05-03 | 1947-12-23 | Process for obtaining a colored image free from metallic silver, and image obtained by this process. |
ES0181502A ES181502A1 (en) | 1944-05-03 | 1947-12-31 | A PROCEDURE FOR OBTAINING A COLORED IMAGE IN A LAYER OF EMULSION TO SILVER HALOGENIDES. |
DEE2173A DE902582C (en) | 1944-05-03 | 1950-09-22 | Process for developing a color image in a silver halide emulsion layer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US533931A US2455169A (en) | 1944-05-03 | 1944-05-03 | Colored couplers |
Publications (1)
Publication Number | Publication Date |
---|---|
US2455169A true US2455169A (en) | 1948-11-30 |
Family
ID=24128024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US533931A Expired - Lifetime US2455169A (en) | 1944-05-03 | 1944-05-03 | Colored couplers |
Country Status (7)
Country | Link |
---|---|
US (1) | US2455169A (en) |
BE (1) | BE476360A (en) |
CH (2) | CH280513A (en) |
DE (1) | DE902582C (en) |
ES (1) | ES181502A1 (en) |
FR (1) | FR950286A (en) |
NL (1) | NL71530C (en) |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2515691A (en) * | 1946-08-21 | 1950-07-18 | Gevaert Photo Prod Nv | Azo dyestuffs as photographic coupling components |
US2521908A (en) * | 1947-03-13 | 1950-09-12 | Eastman Kodak Co | 1-hydroxy-2-naphthamide colored couplers |
US2725292A (en) * | 1952-05-15 | 1955-11-29 | Eastman Kodak Co | Colored couplers containing solubilizing groups |
US2725291A (en) * | 1952-05-01 | 1955-11-29 | Eastman Kodak Co | Azo dye couplers having two coupling nuclei |
US3148062A (en) * | 1959-04-06 | 1964-09-08 | Eastman Kodak Co | Photographic elements and processes using splittable couplers |
US3227554A (en) * | 1959-04-06 | 1966-01-04 | Eastman Kodak Co | Photographic elements and processes utilizing mercaptan-forming couplers |
US3227550A (en) * | 1962-09-07 | 1966-01-04 | Eastman Kodak Co | Photographic color reproduction process and element |
US3625919A (en) * | 1967-02-10 | 1971-12-07 | Hiroyoshi Kamogawa | Process for the preparation of diazotized vinylphenol polymers having phototropic properties |
US3647468A (en) * | 1967-05-15 | 1972-03-07 | Ferrania Spa | Photographic silver halide elements having magenta-colored coupler dyes |
US3977825A (en) * | 1973-06-22 | 1976-08-31 | L'oreal | Indoanilines in keratinic fiber dye cmpositions |
US4007747A (en) * | 1973-12-12 | 1977-02-15 | Societe Anonyme Dite: L'oreal | N-monosubstituted indoanilines as dyestuffs for keratinic fibers |
US4379819A (en) * | 1980-04-30 | 1983-04-12 | Ciba-Geigy Ag | Color-photographic recording material for the silver dye bleach process |
US4777120A (en) * | 1987-05-18 | 1988-10-11 | Eastman Kodak Company | Photographic element and process comprising a masking coupler |
US4871655A (en) * | 1987-01-16 | 1989-10-03 | Konica Corporation | Light-sensitive silver halide color photographic material containing multi-functional dye |
US5100760A (en) * | 1986-02-24 | 1992-03-31 | Fuji Photo Film Co., Ltd. | Light-sensitive material containing silver halide, reducing agent and polymerizable compound |
EP0695968A2 (en) | 1994-08-01 | 1996-02-07 | Eastman Kodak Company | Viscosity reduction in a photographic melt |
EP0779544A1 (en) | 1995-12-11 | 1997-06-18 | Eastman Kodak Company | Photographic element containing an improved pyrazolotriazole coupler |
EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
WO2013032827A1 (en) | 2011-08-31 | 2013-03-07 | Eastman Kodak Company | Motion picture films to provide archival images |
CN114933818A (en) * | 2022-06-28 | 2022-08-23 | 绍兴文理学院 | Indoline disperse dye and preparation method thereof |
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US2304820A (en) * | 1939-10-24 | 1942-12-15 | Du Pont | Substituted monoamides of aliphatic dibasic acids |
US2308023A (en) * | 1938-10-26 | 1943-01-12 | Eastman Kodak Co | Colored photographic image |
US2322006A (en) * | 1939-12-29 | 1943-06-15 | Eastman Kodak Co | Photographic filter and antihalation layer |
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US2367531A (en) * | 1942-06-12 | 1945-01-16 | Eastman Kodak Co | Acylaminophenol photographic couplers |
-
0
- BE BE476360D patent/BE476360A/xx unknown
- NL NL71530D patent/NL71530C/xx active
-
1944
- 1944-05-03 US US533931A patent/US2455169A/en not_active Expired - Lifetime
-
1946
- 1946-08-29 FR FR950286D patent/FR950286A/en not_active Expired
-
1947
- 1947-12-23 CH CH280513D patent/CH280513A/en unknown
- 1947-12-23 CH CH282410D patent/CH282410A/en unknown
- 1947-12-31 ES ES0181502A patent/ES181502A1/en not_active Expired
-
1950
- 1950-09-22 DE DEE2173A patent/DE902582C/en not_active Expired
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Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2515691A (en) * | 1946-08-21 | 1950-07-18 | Gevaert Photo Prod Nv | Azo dyestuffs as photographic coupling components |
US2521908A (en) * | 1947-03-13 | 1950-09-12 | Eastman Kodak Co | 1-hydroxy-2-naphthamide colored couplers |
US2725291A (en) * | 1952-05-01 | 1955-11-29 | Eastman Kodak Co | Azo dye couplers having two coupling nuclei |
US2725292A (en) * | 1952-05-15 | 1955-11-29 | Eastman Kodak Co | Colored couplers containing solubilizing groups |
US3148062A (en) * | 1959-04-06 | 1964-09-08 | Eastman Kodak Co | Photographic elements and processes using splittable couplers |
US3227554A (en) * | 1959-04-06 | 1966-01-04 | Eastman Kodak Co | Photographic elements and processes utilizing mercaptan-forming couplers |
US3227550A (en) * | 1962-09-07 | 1966-01-04 | Eastman Kodak Co | Photographic color reproduction process and element |
US3625919A (en) * | 1967-02-10 | 1971-12-07 | Hiroyoshi Kamogawa | Process for the preparation of diazotized vinylphenol polymers having phototropic properties |
US3647468A (en) * | 1967-05-15 | 1972-03-07 | Ferrania Spa | Photographic silver halide elements having magenta-colored coupler dyes |
US3977825A (en) * | 1973-06-22 | 1976-08-31 | L'oreal | Indoanilines in keratinic fiber dye cmpositions |
US4007747A (en) * | 1973-12-12 | 1977-02-15 | Societe Anonyme Dite: L'oreal | N-monosubstituted indoanilines as dyestuffs for keratinic fibers |
US4379819A (en) * | 1980-04-30 | 1983-04-12 | Ciba-Geigy Ag | Color-photographic recording material for the silver dye bleach process |
US5100760A (en) * | 1986-02-24 | 1992-03-31 | Fuji Photo Film Co., Ltd. | Light-sensitive material containing silver halide, reducing agent and polymerizable compound |
US4871655A (en) * | 1987-01-16 | 1989-10-03 | Konica Corporation | Light-sensitive silver halide color photographic material containing multi-functional dye |
US4777120A (en) * | 1987-05-18 | 1988-10-11 | Eastman Kodak Company | Photographic element and process comprising a masking coupler |
EP0695968A2 (en) | 1994-08-01 | 1996-02-07 | Eastman Kodak Company | Viscosity reduction in a photographic melt |
EP0779544A1 (en) | 1995-12-11 | 1997-06-18 | Eastman Kodak Company | Photographic element containing an improved pyrazolotriazole coupler |
EP1914594A2 (en) | 2004-01-30 | 2008-04-23 | FUJIFILM Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
WO2013032827A1 (en) | 2011-08-31 | 2013-03-07 | Eastman Kodak Company | Motion picture films to provide archival images |
CN114933818A (en) * | 2022-06-28 | 2022-08-23 | 绍兴文理学院 | Indoline disperse dye and preparation method thereof |
CN114933818B (en) * | 2022-06-28 | 2024-01-16 | 绍兴文理学院 | Indoline disperse dye and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
NL71530C (en) | |
BE476360A (en) | |
CH282410A (en) | 1952-04-30 |
CH280513A (en) | 1952-01-31 |
ES181502A1 (en) | 1948-04-16 |
DE902582C (en) | 1954-01-25 |
FR950286A (en) | 1949-09-22 |
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