US2892714A - Photographic color development with pyrazoline developers - Google Patents
Photographic color development with pyrazoline developers Download PDFInfo
- Publication number
- US2892714A US2892714A US520608A US52060855A US2892714A US 2892714 A US2892714 A US 2892714A US 520608 A US520608 A US 520608A US 52060855 A US52060855 A US 52060855A US 2892714 A US2892714 A US 2892714A
- Authority
- US
- United States
- Prior art keywords
- amino
- pyrazoline
- color
- developers
- color development
- 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
Links
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 title description 2
- -1 SILVER HALIDE Chemical class 0.000 claims description 18
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 239000004332 silver Substances 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UQRQFLMLMSIRPO-UHFFFAOYSA-N 2-(4-aminophenyl)-1,3-dihydropyrazol-5-amine Chemical class N1C(N)=CCN1C1=CC=C(N)C=C1 UQRQFLMLMSIRPO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- OQDMCDIRPZVTFZ-UHFFFAOYSA-N 1,3-dihydropyrazol-2-amine Chemical compound NN1CC=CN1 OQDMCDIRPZVTFZ-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- CWZRXXJJOCTIJA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazol-5-amine Chemical compound NC1=CCNN1 CWZRXXJJOCTIJA-UHFFFAOYSA-N 0.000 description 1
- 241001479434 Agfa Species 0.000 description 1
- 241001233887 Ania Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
- G03C5/3028—Heterocyclic compounds
- G03C5/3035—Heterocyclic compounds containing a diazole ring
Definitions
- the present invention relates to a process for the production of photographic color images by color development and more especially to such processes in which 1-(4'-aminophenyl)-3-amino-pyrazolines are used as color forming developing substances.
- Examples of such compounds are: 1-(4'-amino- 3' methoxyphenyl) 3 aminopyrazoline dihydrochloride, 1 (4 amino 3 methylphenyl) 3 aminopyrazolinedihydrochloride, 1 -(4" aminophenyl 2- hydrochloride, 1-(4-amino- I V I inopyrazolinedihydrochloride, (4- amino- 3' ca'rboxyethylphenyl) 3 aminomthyld aminopyrazolin iiyrgfzolinediliydrochldride.
- l-(p-aminophenyl)-3-aminopyrazoline may be obtained by 1-(p-acylaminophenyl)-3-aminopyrazolines, such as, for example, the acetyl derivative, being subjected to alkali saponification.
- the derivatives of this compound may be prepared in analogous manner (see in this connection application relating to Process for the production of l-(p-a'rninophenyl)-3-aminopyrazoline Serial No. 515,558 filed June 14, 1955, by Rudolf Mersch and D'e'tlef Delfs, now U. S. Patent 2,840,567, granted June 24, 1958, and assigned to the assignee of the present application.
- Example 7 of that application discloses that the above acetyl den'vative is made by introducing one mol of N-nitroso- N-'(p'-'acetaminophenyl)-beta amino propionitrile and 200 grams of zinc dust into 2 liters of 10% acetic acid, after the reductionis complete filtering OK the zinc slurry with suction, washing with hot acetic acid and supersaturating the filtrate with acetic acid.
- the l-(p-acetyl amino phenyl)-3-aminopyrazoline precipitates out in good yield and hasa'i'rieltingpoint of 204 C.
- Example 1 An exposed photographic silver halide emulsion, in which is incorporated l-(4-sulphophenyl)-3palmity1- pyrazolone(5) as color coupler, was developed in a developer solution of the following composition at 18 to a gamma equal to 0.7
- Example 2 An exposed photographic silver halide emulsion having incorporated 1-(4-sulphophenyl)-3-palmityl-pyrazolone() as color coupler, was developed in a developer solution of the following composition to a gamma of 0.7:
- Example 3 1-(4-amino-3'-chloro-phenyl)-3-amino pyrazoline dihydrochloride 3 1.5 Potassium carbonate g 70 Potassium bromide g 2 Sodium sulphite g 3 Water es..- 1
- the desired gamma was obtained after a development time of 4 minutes; the relative sensitivity was 2.0.
- Example 4 An exposed photographic silver halide emulsion having incorporated 5-(4'-stearoyl amino benzoyl aceton)- aminoisophthalic acid as color coupler, was developed in a developer solution of the following composition to a gamma of 0.7:
- Example 5 1-(4'-amino-2-methyl phenyD-3-amino pyrazolinedihydrochloride g 1.2 Potassium carbonate g 70 Potassium bromide E 2 Sodium sulphite "g-.. 3 Water litres..- 1
- the desired gamma was obtained after a development time of 3 minutes; the relative sensitivity was 2.0.
- Example 6 An exposed photographic silver halide emulsion having incorporated 1-(4'-sulphophenyl)-3-palmityl-pyrazolone(5) as color coupler was developed in a developer solution of the following composition to a gamma of 0.7:
- the desired gamma was obtained after a development time of 4 minutes; the relative sensitivity was 2.5.
- Example 7 An exposed photographic silver halide emulsion having incorporated 1-hydroxy-4-sulfo-2-naphthoic acid stearyl anilide as color coupler was developed in a tie veloper solution of the following composition to a gamma of 0.7:
- the 1-(4'-aminophenyl)-3-amino-pyrazoline is produced by refluxing 21.8 grams of l-(p-acetoarninophenyl)-3-aminopyrazoline (M.P. 204 C.) with 220 ml. of 5% aqueous sodium hydroxide solution for 6 hours and thereafter cooling the reaction mass. The crystals obtained melt at about C. with decomposition.
- the l-(p-acetoaminophenyl)-3-aminopyrazoline is prepared in accordance with the disclosure contained in Example 14 of British Patent No. 679,678.
- a process for the production of colored photo graphic images which comprises providing a photographic silver halide emulsion with a latent image and developing this image with an alkaline aqueous solution of a developer which is essentially a compound of the formula:
- R stands for a member .of the group consisting of hydrogen, alkyl, alkoxy and halogen, this development being carried out in the presence of a color coupler capable of reacting with the oxidation product of said compound to form a dye.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
United States Patent PHOTOGRAPHIC COLOR DEVELOPMENT PYRAZOLINE DEVELOPERS Ottmar Wahl, Opladen, Rudolf Mersch, Leverkusen- Bayerwerk, and Walter Piiscli'el, Dusseldorfi-G'ermany, assiguors to AGFA Aktiengesellschaft, Leverkilsen, Germany, a corporation of Germany No Drawing. Application July 7, 1955 Serial No. 520,608
Claims priority, application Germany July 8, 195 1 2 Claims. (CI. 96-55) The present invention relates to a process for the production of photographic color images by color development and more especially to such processes in which 1-(4'-aminophenyl)-3-amino-pyrazolines are used as color forming developing substances.
In the production of colored images by color forming development of exposed silver halide emulsion layers, a colored image is formed in addition to the silver image by the oxidation product of the developer reacting with color couplers which are present at the same time, thereby forming a dye. Particular practical importance has formerly been assumed by those processes in which p-phenylene diamine or its derivatives have been used as developer. p-Aminophenol and its derivatives have also been described for this purpose.
It has now been found that novel effects such as were not possible with the hitherto known developers may be produced with 1-(p-arninophenyl)3-aminopyrazoline and its derivatives in the color development of exposed silver halide emulsions. The derivatives of l-(p-an'iinophenyl)-3-aminopyrazoline are obtained by substitution of the hydrogen atoms in the l-phenyl nucleus and in the heterocyclic ring, and as 's'iibstitiidiit's, there "are mentioned, by way of example, alkyl, aryl, aralkyl, acyl, alkoxy, carboxy, amino, hydroxyl, halogen and sulpho groups. Examples of such compounds are: 1-(4'-amino- 3' methoxyphenyl) 3 aminopyrazoline dihydrochloride, 1 (4 amino 3 methylphenyl) 3 aminopyrazolinedihydrochloride, 1 -(4" aminophenyl 2- hydrochloride, 1-(4-amino- I V I inopyrazolinedihydrochloride, (4- amino- 3' ca'rboxyethylphenyl) 3 aminomthyld aminopyrazolin iiyrgfzolinediliydrochldride.
Whereas, for. example, 1-(p-aminophenyl)-4-aminopyrazolones have not been found suitable -for effective color-developingthe compounds according to the present shades {of the dyestufis 'which are obtained' by the couh pling oi the development products of these compounds with color couplers in color development are very different as compared with those which are obtained with the knciwn p-phenylene diamines. As will be seen from the following Example 1, the absorption maximum of "the "dyestuffs "obtained is displaced by up to 100 rm "to- 2,892,714 Patented June 30, 1959 Ice wards longer wave length. In addition essential differences are shown in other properties or the dyestuffs as compared with the corresponding dyestuffs obtained with the known color developers, for example, as regards increased resistance to acid. Owing to the increased developing and coupling intensity, it is possible to obtain additional advantages as regards the sensitivity of the material for color photography.
l-(p-aminophenyl)-3-aminopyrazoline may be obtained by 1-(p-acylaminophenyl)-3-aminopyrazolines, such as, for example, the acetyl derivative, being subjected to alkali saponification. The derivatives of this compound may be prepared in analogous manner (see in this connection application relating to Process for the production of l-(p-a'rninophenyl)-3-aminopyrazoline Serial No. 515,558 filed June 14, 1955, by Rudolf Mersch and D'e'tlef Delfs, now U. S. Patent 2,840,567, granted June 24, 1958, and assigned to the assignee of the present application. Furthermore there may be applied the process disclosed in the copending application Serial No. 440,562, filed June 30, 1952 and now abandoned. Example 7 of that application discloses that the above acetyl den'vative is made by introducing one mol of N-nitroso- N-'(p'-'acetaminophenyl)-beta amino propionitrile and 200 grams of zinc dust into 2 liters of 10% acetic acid, after the reductionis complete filtering OK the zinc slurry with suction, washing with hot acetic acid and supersaturating the filtrate with acetic acid. The l-(p-acetyl amino phenyl)-3-aminopyrazoline precipitates out in good yield and hasa'i'rieltingpoint of 204 C.
Example 1 An exposed photographic silver halide emulsion, in which is incorporated l-(4-sulphophenyl)-3palmity1- pyrazolone(5) as color coupler, was developed in a developer solution of the following composition at 18 to a gamma equal to 0.7
l-(p-aminoph enyl)-3-aminopyrazoline chloride g.. 0.9
Potassium carbonate ..g Potassium bromide g 2 Sodium sulphite g 3 Water litre 1 The required .gamma was reached after a development A period of 7 minutes at 18 was necessary in this developer to reach a gamma equal to 0.7.
The following table shows the color displacement produced according to the invention as compared with the color development with 4-amino-ethyl-hydroxyethyl ania line,'using difierent color couplers:
Example 2 An exposed photographic silver halide emulsion having incorporated 1-(4-sulphophenyl)-3-palmityl-pyrazolone() as color coupler, was developed in a developer solution of the following composition to a gamma of 0.7:
l-(4'-amino-3'-methoxy phenyl)-3-amino pyrazolinedihydrochloride g 0.7 Potassium carbonate 70 Potassium bromide Q 2 Sodium sulphite g 3 Water es- 1 The desired gamma was obtained after a development time of 3 minutes; the relative sensitivity was to 2.5.
Example 3 1-(4-amino-3'-chloro-phenyl)-3-amino pyrazoline dihydrochloride 3 1.5 Potassium carbonate g 70 Potassium bromide g 2 Sodium sulphite g 3 Water es..- 1
The desired gamma was obtained after a development time of 4 minutes; the relative sensitivity was 2.0.
Example 4 An exposed photographic silver halide emulsion having incorporated 5-(4'-stearoyl amino benzoyl aceton)- aminoisophthalic acid as color coupler, was developed in a developer solution of the following composition to a gamma of 0.7:
1-(4'-amino-3'-methyl phenyl)-3-amino pyrazoline dihydrochloride g 0.9 Potassium carbonate 70 Potassium bromide Q 2 Sodium sulphite g 3 Water es" 1 The desired gamma was obtained after a development time of 3 minutes; the relative sensitivity was 2.5.
Example 5 1-(4'-amino-2-methyl phenyD-3-amino pyrazolinedihydrochloride g 1.2 Potassium carbonate g 70 Potassium bromide E 2 Sodium sulphite "g-.. 3 Water litres..- 1
The desired gamma was obtained after a development time of 3 minutes; the relative sensitivity was 2.0.
Example 6 An exposed photographic silver halide emulsion having incorporated 1-(4'-sulphophenyl)-3-palmityl-pyrazolone(5) as color coupler was developed in a developer solution of the following composition to a gamma of 0.7:
1 (4-amino-3'-methoxy phenyl)-3-aminopyrazoline dihydrochloride g 0.7 Sodium carbonate g 50 Potassium bromide Q 2 Sodium sulphite g 3 Water litres-.. 1
The desired gamma was obtained after a development time of 4 minutes; the relative sensitivity was 2.5.
Example 7 An exposed photographic silver halide emulsion having incorporated 1-hydroxy-4-sulfo-2-naphthoic acid stearyl anilide as color coupler was developed in a tie veloper solution of the following composition to a gamma of 0.7:
1-(4-amino-3-chloro phenyD-S-amino pyrazoline di- The desired gamma was obtained after a development time of 5 minutes; the relative sensitivity Was 2.5.
The 1-(4'-aminophenyl)-3-amino-pyrazoline is produced by refluxing 21.8 grams of l-(p-acetoarninophenyl)-3-aminopyrazoline (M.P. 204 C.) with 220 ml. of 5% aqueous sodium hydroxide solution for 6 hours and thereafter cooling the reaction mass. The crystals obtained melt at about C. with decomposition. The l-(p-acetoaminophenyl)-3-aminopyrazoline is prepared in accordance with the disclosure contained in Example 14 of British Patent No. 679,678.
The two further pyrazolines referred to above are produced in analogous manner.
What we claim is:
l. A process for the production of colored photo graphic images which comprises providing a photographic silver halide emulsion with a latent image and developing this image with an alkaline aqueous solution of a developer which is essentially a compound of the formula:
in which R stands for a member .of the group consisting of hydrogen, alkyl, alkoxy and halogen, this development being carried out in the presence of a color coupler capable of reacting with the oxidation product of said compound to form a dye.
2. A process according to claim 1 wherein the developer compound is 1-(4'-aminophenyl)-3-amino pyrazoline.
References Cited in the file of this patent UNITED STATES PATENTS 2,533,514 Sawdey et a1 Dec. 12, 1950
Claims (1)
1. A PROCESS FOR THE PRODUCTION OF COLORED PHOTOGRAPHIC IMAGES WHICH COMPRISES PROVIDING A PHOTOGRAPHIC SILVER HALIDE EMULSION WITH A LATENT IMAGE AND DEVELOPING THIS IMAGE WITH AN ALKALINE AQUEOUS SOLUTION OF A DEVELOPER WHICH IS ESSENTIALLY A COMPOUND OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA20693A DE955026C (en) | 1954-07-08 | 1954-07-08 | Process for producing colored images by color development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2892714A true US2892714A (en) | 1959-06-30 |
Family
ID=6924750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US520608A Expired - Lifetime US2892714A (en) | 1954-07-08 | 1955-07-07 | Photographic color development with pyrazoline developers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2892714A (en) |
| BE (1) | BE539271A (en) |
| CH (1) | CH336259A (en) |
| DE (1) | DE955026C (en) |
| FR (1) | FR1126757A (en) |
| GB (1) | GB795476A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3212894A (en) * | 1960-12-24 | 1965-10-19 | Agfa Ag | Non-diffusing magenta color couplers |
| US3547646A (en) * | 1966-12-16 | 1970-12-15 | Keuffel & Esser Co | Light-sensitive imaging material containing hydrazones |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2533514A (en) * | 1947-11-19 | 1950-12-12 | Eastman Kodak Co | Photographic emulsions containing color couplers and amide coupler solvents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB542502A (en) * | 1940-07-10 | 1942-01-13 | John David Kendall | Improvements in or relating to photographic development processes |
| DE870418C (en) * | 1950-04-06 | 1953-03-12 | Ilford Ltd | Process for the preparation of pyrazoline compounds |
| DE875048C (en) * | 1950-04-06 | 1953-04-30 | Ilford Ltd | Process for the preparation of 3-pyrazolidones |
-
0
- BE BE539271D patent/BE539271A/xx unknown
-
1954
- 1954-07-08 DE DEA20693A patent/DE955026C/en not_active Expired
-
1955
- 1955-06-15 CH CH336259D patent/CH336259A/en unknown
- 1955-06-28 FR FR1126757D patent/FR1126757A/en not_active Expired
- 1955-07-07 US US520608A patent/US2892714A/en not_active Expired - Lifetime
- 1955-07-08 GB GB19856/55A patent/GB795476A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2533514A (en) * | 1947-11-19 | 1950-12-12 | Eastman Kodak Co | Photographic emulsions containing color couplers and amide coupler solvents |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3212894A (en) * | 1960-12-24 | 1965-10-19 | Agfa Ag | Non-diffusing magenta color couplers |
| US3547646A (en) * | 1966-12-16 | 1970-12-15 | Keuffel & Esser Co | Light-sensitive imaging material containing hydrazones |
Also Published As
| Publication number | Publication date |
|---|---|
| GB795476A (en) | 1958-05-21 |
| DE955026C (en) | 1956-12-27 |
| BE539271A (en) | |
| CH336259A (en) | 1959-02-15 |
| FR1126757A (en) | 1956-11-30 |
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