US2524725A - Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers - Google Patents
Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers Download PDFInfo
- Publication number
- US2524725A US2524725A US793536A US79353647A US2524725A US 2524725 A US2524725 A US 2524725A US 793536 A US793536 A US 793536A US 79353647 A US79353647 A US 79353647A US 2524725 A US2524725 A US 2524725A
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- US
- United States
- Prior art keywords
- phenazonium
- magenta
- hydroxyquinoline
- acid
- color
- 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
-
- 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
- G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
Definitions
- the present invention relates to color formers of the 8-hydroxyquinoline class, which are particularly suitable for the production of magenta phenazonium dyestuff images by color development of an exposed silver halide emulsion with an orthophenylene diamine type color developer.
- R is an electronegative group such as a halogen, i. e., chlorine or bromine, or a mononuclear carbocyclic aromatic radical such as phenyl, nitro-phenyl, amino-phenyl, alkyl-sulfonamido-phenyl, alkyl-carboxamido-phenyl, in
- the alkyl radical may contain 10 or more carbon atoms, and the like, and R represents hydrogen, carboxy, or a carboxamido group containing an alkyl chain of at least 10,
- carbon atoms such as tetradecanoylamino, decanoylamino, dodecanoylamino, stearoylamino, and the like, or acylaminoaryl-carbamyl, such as stearoylamino benzene carbamyl, stearoyl- 5 methyl-sulfobenzene-carbamyl, and the like.
- the color developers which are utilized are as stated of the ortho-phenylenediamine class, a large number of examples of which are referred to in the aforesaid Schmidt and Tulagin application.
- Suitable color developers are, for example: 4,6-dianilino metanilic acid, 4,6-bis-(omethoxy-phenylamino) metanilic acid, 4-(ncarboxy-phenylamino)- fi-(p-methoxy-phenylamino) phenylamino)-metanilic acid, and the like.
- the crux of the present invention is the color formers, and that any ortho-phenylene diamine tylpe developer may be used "with the color formers in producing the desired magenta phenazonium dye images.
- the majority of the color formers previously referred to are known compounds. Those which are not described in the literature, such as that of Exam les 3, 4, 8 and 11, can be prepared by the usual amidation reaction.
- the compound No. 3 may be obtained by reacting 2- metanilic acid, 4,6-bis-(p-methoxy- (3-aminophenyl) -8-hydroxy cinchoninic acid with decyl sulfonyl chloride in the presence of an acid-binding agent such as pyridine.
- an acid-binding agent such as pyridine.
- a similar procedure is employed in producing the compound No. 4, the only difference being that lauryl sulfonyl chloride is used in forming the sulfonamide.
- Compound No. 8 may be prepared by reacting 2-(3-amino-phenyl)S-hydroxy cinchoninic acid with myristoyl chloride in the presence of an acid-binding agent such as pyridine.
- Compound No. 10 may be formed by treating equimolecular proportions of 2-phenyl-8-hydroxy cinchoninic acid and octadecyl-taurine in pyridine solution with an excess of phosphorus trichloride dissolved in pyridine.
- Compound No. 11 is formed by treating equimolecular proportions of 2-phenyl-8-hydroxy cinchoninic acid and 3-amino-6-stearoylamino- 4-toluenesulfonic acid in pyridine with an excessof phosphorus trichloride dissolved in pyridine.
- Example 2 .5 gram of 2-(3-decylsulfonamidophenyl) -8- hydroxy cinchoninic acid is dissolved in 10 ml. of water by the addition of 1 Nsodium hydroxide solution. The solution of the color former is then added to 50 grams of a silver bromide emulsion and the emulsion coated on a iilm base.
- the film after drying is exposed and developed with the developer of Example 1, excepting that the. 2-ch1oro-8-hydroxyquinoline is omitted from the developing solution.
- Example 2 After working up the film as in. Example 1, there is obtained a brilliant magenta dyestuff image having a high spectral transmission.
- Example 3 emulsion with a 2,4-diamino aniline developer in the presence of a color former having the following formula:
- R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical, and R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least carbon atoms.
- a photographic developer for the production of magenta phenazonium dyestuff images com prising an alkaline solution containing as its essential components a 2,4-diamino aniline developer and as the color former a compound of the following formula: I
- R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical, and R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least 10 carbon atoms.
- a photographic silver halide emulsion con- 7 taining as a color former capable of yielding magenta phenazonium dyestufi images a compound of the following formula:
- R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical
- R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least 10 carbon atoms, at least one of the radicals R and R containing an alkyl chain of at least 10 carbon atoms.
Description
Patented Oct. 3., 1950 MAGENTA PI-IENAZONIUM DYESTUFF IM- AGES FROM S-HYDROXYQUINOLINE COUPLERS Robert F. Coles, Easton, Pa., assignor to General Aniline & Film Corporation, New York, N. Y., a corporation of Delaware N Drawing. Application December 23, 1947,
Serial No. 793,536 6 6 Claims.
T The present invention relates to color formers of the 8-hydroxyquinoline class, which are particularly suitable for the production of magenta phenazonium dyestuff images by color development of an exposed silver halide emulsion with an orthophenylene diamine type color developer.
In the copending application Serial No. 640,382, filed On January 10, 1946, of Willy A. Schmidt and Vsevolod Tulagin, now Patent No. 2,486,440, there is described the production of phenazonium 'dyestuff images by color developing an exposed silver halide emulsion with a color developer comprising an ortho-phenylene diamine in the presence of a color former which may be inter alia 8-hydroxyquinoline.
It has now been discovered that the method of said application can be practiced to yield phenazonium dyestuff images having a markedly improved magenta transmission spectra by utilizing as the color formers S-hydroxyquinolines (including 8-hydroxy cinchoninic acids) containing in the 2 position of the nucleusthereof an electronegative substituent such as a halogen or a mononuclear carbocyclic aromatic radical. It has been further found that such compounds readily lend themselves to the introduction of long alkyl chains to thereby render the color formers non-migratory in photographic emulsions, thus facilitating the employment of'the picted by the following structural formula:
wherein R is an electronegative group such as a halogen, i. e., chlorine or bromine, or a mononuclear carbocyclic aromatic radical such as phenyl, nitro-phenyl, amino-phenyl, alkyl-sulfonamido-phenyl, alkyl-carboxamido-phenyl, in
which if desired the alkyl radical may contain 10 or more carbon atoms, and the like, and R represents hydrogen, carboxy, or a carboxamido group containing an alkyl chain of at least 10,
carbon atoms, such as tetradecanoylamino, decanoylamino, dodecanoylamino, stearoylamino, and the like, or acylaminoaryl-carbamyl, such as stearoylamino benzene carbamyl, stearoyl- 5 methyl-sulfobenzene-carbamyl, and the like.
Examples of compounds embraced by the above formula are the following:
2-chloro-8-hydroxyquino1ine 2. OOOH OH 2-phenyl-8-hydroxy-cinchoninic acid 3. o 0 OH i I? NS mHzi N 7 1 O V H 2- (3-decylsulfonamidophenyl)-8-hydroxy cinchoninic acid 4. O O OH t I? N-fi-O12H25 2-(3-dodecylsulfonamidophenyl)-8-hydroxy cinchoninic acid Br N 60 v 2-bromo-8-hydroxy-quinoline H e 2 (3 -nitrophenyl) -8-hy droxy-quin oline 2 (3-aminophenyl) -8-hydroxy-quinoline 2-(3-myristoylaminophenyl)-8-hydroxy cinchoninic acid 9. C O OH Br N 611 2-bromo-8-hydroxy cinchoninic acid CzH4SO3H C1s a1 (Shydroxy-Z-phenylcinchoninoyl) -octadecy1tau rine I S OaH 7 -stearoylamino-3- (8-hydroxy-2-phenylcinchoninoyl) amino-4-toluenesulfonic acid persed in the photographic emulsions in order.
to be operable to produce the desired images on color forming development.
The color developers, which are utilized are as stated of the ortho-phenylenediamine class, a large number of examples of which are referred to in the aforesaid Schmidt and Tulagin application. Suitable color developers are, for example: 4,6-dianilino metanilic acid, 4,6-bis-(omethoxy-phenylamino) metanilic acid, 4-(ncarboxy-phenylamino)- fi-(p-methoxy-phenylamino) phenylamino)-metanilic acid, and the like.
It is to be understood that the crux of the present invention is the color formers, and that any ortho-phenylene diamine tylpe developer may be used "with the color formers in producing the desired magenta phenazonium dye images.
The majority of the color formers previously referred to are known compounds. Those which are not described in the literature, such as that of Exam les 3, 4, 8 and 11, can be prepared by the usual amidation reaction. For instance, the compound No. 3 may be obtained by reacting 2- metanilic acid, 4,6-bis-(p-methoxy- (3-aminophenyl) -8-hydroxy cinchoninic acid with decyl sulfonyl chloride in the presence of an acid-binding agent such as pyridine. A similar procedure is employed in producing the compound No. 4, the only difference being that lauryl sulfonyl chloride is used in forming the sulfonamide.
Compound No. 8 may be prepared by reacting 2-(3-amino-phenyl)S-hydroxy cinchoninic acid with myristoyl chloride in the presence of an acid-binding agent such as pyridine.
Compound No. 10 may be formed by treating equimolecular proportions of 2-phenyl-8-hydroxy cinchoninic acid and octadecyl-taurine in pyridine solution with an excess of phosphorus trichloride dissolved in pyridine.
Compound No. 11 is formed by treating equimolecular proportions of 2-phenyl-8-hydroxy cinchoninic acid and 3-amino-6-stearoylamino- 4-toluenesulfonic acid in pyridine with an excessof phosphorus trichloride dissolved in pyridine.
The invention is illustrated by the following examples, but it is to be understood that these examples are illustrative and not limitative of the invention.
Ewample 1 A photographic silver bromide emulsion is exposed and then color developed for five to ten minutes in a solutionv of the following color developer:
Sodium carbonate monohydrate grams 60 Potassium bromide do 2.5 Sodium sulfite do 40 Pyridine cc. 12 4,6-dianilino metanilic acid grams 4 2-chloro-8-hydroxyquinoline do 2 Water cc. 1000 The developed silver image is bleached with potassium ferricyanide and fixed in an acid hardening hypo solution. There is thus obtained a phenazonium dyestufi image which has a hig magenta transmission spectrum.
Example 2 .5 gram of 2-(3-decylsulfonamidophenyl) -8- hydroxy cinchoninic acid is dissolved in 10 ml. of water by the addition of 1 Nsodium hydroxide solution. The solution of the color former is then added to 50 grams of a silver bromide emulsion and the emulsion coated on a iilm base.
The film after drying is exposed and developed with the developer of Example 1, excepting that the. 2-ch1oro-8-hydroxyquinoline is omitted from the developing solution.
After working up the film as in. Example 1, there is obtained a brilliant magenta dyestuff image having a high spectral transmission.
Example 3 emulsion with a 2,4-diamino aniline developer in the presence of a color former having the following formula:
in which R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical, and R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least carbon atoms.
2. A photographic developer for the production of magenta phenazonium dyestuff images com prising an alkaline solution containing as its essential components a 2,4-diamino aniline developer and as the color former a compound of the following formula: I
in which R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical, and R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least 10 carbon atoms.
3. A photographic silver halide emulsion con- 7 taining as a color former capable of yielding magenta phenazonium dyestufi images a compound of the following formula:
in which R is an electronegative radical selected from the class consisting of halogen and a mononuclear carbocyclic aromatic radical, and R is a member of the class consisting of hydrogen, carboxy and carbonamido groups containing an alkyl chain of at least 10 carbon atoms, at least one of the radicals R and R containing an alkyl chain of at least 10 carbon atoms.
4. The process as defined in claim 1 wherein the color former is 2-chloro-8-hydroxyquinoline.
5. The photographic developer defined in claim 2 wherein the color former is 2-chloro-8-hydroxyquinoline.
6. A'photographic silver halide emulsion containing as a color former 5-stearoylamino-3-(8- hydroxy 2 phenylcinchoninoyl) -amino-4-to1- uenesulfonic acid.
ROBERT F. COLES.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Name Date
Claims (1)
1. THE PROCESS OF PRODUCING MAGENTA PHENAZONIUM DYESTUFF IMAGES IN AN EXPOSED SILVER HALIDE EMULSION WHICH COMPRISES DEVELOPING SAID EMULSION WITH A 2,4-DIAMINO ANILINE DEVELOPER IN THE PRESENCCE OF A COLOR FORMER HAVING THE FOLLOWING FORMULA:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US640382A US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2524725A true US2524725A (en) | 1950-10-03 |
Family
ID=41210569
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US640382A Expired - Lifetime US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
| US793535A Expired - Lifetime US2525503A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US793536A Expired - Lifetime US2524725A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers |
| US793534A Expired - Lifetime US2525502A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US793533A Expired - Lifetime US2524741A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers |
| US101913A Expired - Lifetime US2570116A (en) | 1946-01-10 | 1949-06-28 | Color developers for the production of azine dye images |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US640382A Expired - Lifetime US2486440A (en) | 1946-01-10 | 1946-01-10 | Production of phenazonium dyestuff images |
| US793535A Expired - Lifetime US2525503A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US793534A Expired - Lifetime US2525502A (en) | 1946-01-10 | 1947-12-23 | Production of phenazonium dyestuff images |
| US793533A Expired - Lifetime US2524741A (en) | 1946-01-10 | 1947-12-23 | Magenta phenazonium dyestuff images from 6-substituted-8-hydroxyquinoline couplers |
| US101913A Expired - Lifetime US2570116A (en) | 1946-01-10 | 1949-06-28 | Color developers for the production of azine dye images |
Country Status (6)
| Country | Link |
|---|---|
| US (6) | US2486440A (en) |
| BE (6) | BE470459A (en) |
| CH (5) | CH280516A (en) |
| DE (6) | DE837959C (en) |
| FR (6) | FR939497A (en) |
| GB (5) | GB644863A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701766A (en) * | 1952-06-14 | 1955-02-08 | Gen Aniline & Film Corp | Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents |
| US4503141A (en) * | 1983-03-28 | 1985-03-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials containing couplers with a hydroxyl substituted aromatic heterocyclic sulfonyl group in the ballast group |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2611785A (en) * | 1952-09-23 | N-substituted x | ||
| CH277023A (en) * | 1949-05-03 | 1951-08-15 | Ciba Geigy | Process for the production of an intermediate product. |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US2596926A (en) * | 1949-12-16 | 1952-05-13 | Gen Aniline & Film Corp | Preparation of azine dye images |
| US2594917A (en) * | 1949-12-16 | 1952-04-29 | Gen Aniline & Film Corp | Suppression of proximity development with azine color developers |
| US2618559A (en) * | 1950-03-21 | 1952-11-18 | Gen Aniline & Film Corp | Stain preventing shortstop bath for photographic azine dye images |
| US2623823A (en) * | 1950-03-21 | 1952-12-30 | Gen Aniline & Film Corp | Energizers for aromatic triamino developing agents and suppression of proximity development in azine color developers |
| US2687431A (en) * | 1950-12-20 | 1954-08-24 | Gen Aniline & Film Corp | Process of preparing nitro phenylenediamines |
| BE508676A (en) * | 1951-01-26 | |||
| US2691588A (en) * | 1952-03-14 | 1954-10-12 | Eastman Kodak Co | Photographic developers containing 8-hydroxyquinolines |
| BE526742A (en) * | 1953-02-24 | |||
| GB802553A (en) * | 1955-11-18 | 1958-10-08 | Gen Aniline & Film Corp | Improvements in or relating to colour photographic materials and processes |
| US2945761A (en) * | 1957-07-29 | 1960-07-19 | Eastman Kodak Co | Reactivity of couplers incorporated in photographic emulsions |
| BE576817A (en) * | 1958-04-03 | |||
| US3099559A (en) * | 1959-08-31 | 1963-07-30 | Gen Aniline & Film Corp | Silver-free color reproduction process and composition therefor |
| NL255792A (en) * | 1959-09-11 | |||
| US3050394A (en) * | 1959-09-30 | 1962-08-21 | Gen Aniline & Film Corp | Method of incorporating color couplers in hydrophlic colloids |
| US3077403A (en) * | 1960-05-31 | 1963-02-12 | Gen Aniline & Film Corp | Color former containing bis coupling functions |
| US4511569A (en) * | 1982-08-26 | 1985-04-16 | Schering Corporation | Tricyclic lactams and derivatives useful in increasing cardiac contractility |
| SE8302361D0 (en) * | 1983-04-27 | 1983-04-27 | Astra Laekemedel Ab | NEW TRICYCLIC AMINES |
| US4680299A (en) * | 1984-04-30 | 1987-07-14 | E.I. Du Pont De Nemours And Company | 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof |
| US4847381A (en) * | 1987-08-31 | 1989-07-11 | American Cyanamid Company | 2-Phenyl-4-quinoline carboxylic acids |
| US5260177A (en) * | 1988-03-16 | 1993-11-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US5223386A (en) * | 1989-03-04 | 1993-06-29 | Konica Corporation | Cyan coupler |
| EP0386931A1 (en) * | 1989-03-04 | 1990-09-12 | Konica Corporation | A novel cyan coupler |
| US4990436A (en) * | 1990-01-23 | 1991-02-05 | Eastman Kodak Company | Cyan dye-forming couplers and photographic recording materials containing same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2306410A (en) * | 1936-07-07 | 1942-12-29 | Eastman Kodak Co | Color development |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB178986A (en) * | 1921-02-11 | 1922-05-04 | John Augustus Ward | Improvements in and relating to advertising apparatus |
| US1782356A (en) * | 1927-11-14 | 1930-11-18 | Firm J R Geigy S A | Manufacture of acid dyestuffs of the phenonaphthosafranine series |
| US1886809A (en) * | 1929-09-04 | 1932-11-08 | Gen Aniline Works Inc | Arylated safranines and process of preparing them |
| BE369421A (en) * | 1929-09-09 | |||
| GB458664A (en) * | 1935-03-21 | 1936-12-21 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| DE767652C (en) * | 1936-05-27 | 1953-03-02 | Ig Farbenindustrie Ag | Process for the color development of halogen silver emulsions |
| US2356475A (en) * | 1936-07-07 | 1944-08-22 | Eastman Kodak Co | Phenolic and naphtholic couplers containing sulphonamide groups |
| US2196739A (en) * | 1938-09-23 | 1940-04-09 | Eastman Kodak Co | Photographic developer for color photography |
| GB531312A (en) * | 1939-03-31 | 1941-01-01 | Eastman Kodak Co | Improvements in and relating to colour forming developers and processes of colour development |
| US2193015A (en) * | 1939-05-24 | 1940-03-12 | Eastman Kodak Co | Developer containing sulphonamide groups |
| GB536939A (en) * | 1939-08-24 | 1941-06-03 | Eastman Kodak Co | Improvements in and relating to photographic colour development |
| BE442586A (en) * | 1940-07-31 | |||
| FR956696A (en) * | 1941-08-08 | 1950-02-02 | ||
| FR956698A (en) * | 1941-09-11 | 1950-02-02 | ||
| GB553064A (en) * | 1941-09-25 | 1943-05-06 | Eastman Kodak Co | Improvements in photographic developers |
| US2364350A (en) * | 1941-11-06 | 1944-12-05 | Eastman Kodak Co | Photographic developer |
| US2400872A (en) * | 1942-09-01 | 1946-05-28 | Eastman Kodak Co | Diamino-nu-alkyl phenazinium salts |
| US2394527A (en) * | 1942-11-04 | 1946-02-05 | Du Pont | Color photography |
| GB576891A (en) * | 1944-05-12 | 1946-04-25 | John David Kendall | Improvements in or relating to colour photography |
| BE465025A (en) * | 1945-01-27 | |||
| US2489440A (en) * | 1945-05-03 | 1949-11-29 | Naylor Brothers Ltd | Conveyer |
| US2445252A (en) * | 1947-04-10 | 1948-07-13 | Gen Aniline & Film Corp | Photographic elements containing urethanes of nu-substituted j acids as color formers |
-
1946
- 1946-01-10 US US640382A patent/US2486440A/en not_active Expired - Lifetime
- 1946-12-11 GB GB36617/46A patent/GB644863A/en not_active Expired
-
1947
- 1947-01-03 FR FR939497D patent/FR939497A/en not_active Expired
- 1947-01-10 BE BE470459D patent/BE470459A/xx unknown
- 1947-12-23 US US793535A patent/US2525503A/en not_active Expired - Lifetime
- 1947-12-23 US US793536A patent/US2524725A/en not_active Expired - Lifetime
- 1947-12-23 US US793534A patent/US2525502A/en not_active Expired - Lifetime
- 1947-12-23 US US793533A patent/US2524741A/en not_active Expired - Lifetime
-
1948
- 1948-12-10 FR FR58855D patent/FR58855E/en not_active Expired
- 1948-12-10 FR FR61006D patent/FR61006E/en not_active Expired
- 1948-12-10 FR FR61007D patent/FR61007E/en not_active Expired
- 1948-12-10 FR FR61005D patent/FR61005E/en not_active Expired
- 1948-12-10 FR FR61004D patent/FR61004E/en not_active Expired
- 1948-12-14 DE DEP24682A patent/DE837959C/en not_active Expired
- 1948-12-14 GB GB32321/48A patent/GB647638A/en not_active Expired
- 1948-12-14 DE DEP24683A patent/DE850385C/en not_active Expired
- 1948-12-14 GB GB32322/48A patent/GB646490A/en not_active Expired
- 1948-12-14 GB GB32257/48A patent/GB646348A/en not_active Expired
- 1948-12-14 DE DEP24684D patent/DE854889C/en not_active Expired
- 1948-12-14 GB GB32258/48A patent/GB649811A/en not_active Expired
- 1948-12-14 DE DEP24685D patent/DE817554C/en not_active Expired
- 1948-12-14 DE DEP24686D patent/DE851163C/en not_active Expired
- 1948-12-20 CH CH280516D patent/CH280516A/en unknown
- 1948-12-21 BE BE486430D patent/BE486430A/xx unknown
- 1948-12-21 BE BE486433D patent/BE486433A/xx unknown
- 1948-12-21 BE BE486434D patent/BE486434A/xx unknown
- 1948-12-22 CH CH283787D patent/CH283787A/en unknown
- 1948-12-22 CH CH280517D patent/CH280517A/en unknown
- 1948-12-22 CH CH280518D patent/CH280518A/en unknown
- 1948-12-22 CH CH283788D patent/CH283788A/en unknown
-
1949
- 1949-01-01 DE DEP29268A patent/DE848155C/en not_active Expired
- 1949-01-15 BE BE486432D patent/BE486432A/xx unknown
- 1949-01-15 BE BE486431D patent/BE486431A/xx unknown
- 1949-06-28 US US101913A patent/US2570116A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2306410A (en) * | 1936-07-07 | 1942-12-29 | Eastman Kodak Co | Color development |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701766A (en) * | 1952-06-14 | 1955-02-08 | Gen Aniline & Film Corp | Developers for and method of producing phenazonium dyestuff images with p-dialkylaminoaniline developing agents |
| US4503141A (en) * | 1983-03-28 | 1985-03-05 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials containing couplers with a hydroxyl substituted aromatic heterocyclic sulfonyl group in the ballast group |
Also Published As
| Publication number | Publication date |
|---|---|
| DE837959C (en) | 1952-05-05 |
| GB649811A (en) | 1951-01-31 |
| DE850385C (en) | 1952-09-25 |
| FR61004E (en) | 1955-03-23 |
| GB647638A (en) | 1950-12-20 |
| FR61007E (en) | 1955-03-23 |
| DE851163C (en) | 1952-10-02 |
| CH280517A (en) | 1952-01-31 |
| GB646348A (en) | 1950-11-22 |
| FR58855E (en) | 1954-04-06 |
| BE486431A (en) | 1948-12-21 |
| BE486432A (en) | 1949-01-15 |
| BE486430A (en) | 1949-01-16 |
| US2525502A (en) | 1950-10-10 |
| BE486433A (en) | 1949-01-15 |
| US2486440A (en) | 1949-11-01 |
| FR939497A (en) | 1948-11-16 |
| BE486434A (en) | 1949-01-15 |
| US2525503A (en) | 1950-10-10 |
| CH280516A (en) | 1952-01-31 |
| US2524741A (en) | 1950-10-03 |
| FR61006E (en) | 1955-03-23 |
| BE470459A (en) | 1947-02-28 |
| GB646490A (en) | 1950-11-22 |
| CH283787A (en) | 1952-06-30 |
| GB644863A (en) | 1950-10-18 |
| CH280518A (en) | 1952-01-31 |
| DE848155C (en) | 1952-11-04 |
| DE817554C (en) | 1951-10-18 |
| DE854889C (en) | 1952-11-06 |
| FR61005E (en) | 1955-03-23 |
| US2570116A (en) | 1951-10-02 |
| CH283788A (en) | 1952-06-30 |
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