US3305364A - Non-silver halide reducing sulfonamide buffers for photographic developing solutions - Google Patents
Non-silver halide reducing sulfonamide buffers for photographic developing solutions Download PDFInfo
- Publication number
- US3305364A US3305364A US306304A US30630463A US3305364A US 3305364 A US3305364 A US 3305364A US 306304 A US306304 A US 306304A US 30630463 A US30630463 A US 30630463A US 3305364 A US3305364 A US 3305364A
- Authority
- US
- United States
- Prior art keywords
- photographic
- silver halide
- buffers
- sulfonamide
- developer
- 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
- 239000000872 buffer Substances 0.000 title claims description 37
- 229910052709 silver Inorganic materials 0.000 title claims description 21
- 239000004332 silver Substances 0.000 title claims description 21
- 229940124530 sulfonamide Drugs 0.000 title claims description 14
- 150000003456 sulfonamides Chemical class 0.000 title claims description 14
- -1 SILVER HALIDE Chemical class 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- PZVFQOBASICMME-UHFFFAOYSA-N n-ethylmethanesulfonamide Chemical compound CCNS(C)(=O)=O PZVFQOBASICMME-UHFFFAOYSA-N 0.000 description 8
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940085991 phosphate ion Drugs 0.000 description 3
- DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- QSPPRYLTQFCUCH-UHFFFAOYSA-N n-methylethanesulfonamide Chemical compound CCS(=O)(=O)NC QSPPRYLTQFCUCH-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- UZECCNDOASGYNH-UHFFFAOYSA-N 4-cyanobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(C#N)C=C1 UZECCNDOASGYNH-UHFFFAOYSA-N 0.000 description 1
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000876833 Emberizinae Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000483002 Euproctis similis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- CKJBFEQMHZICJP-UHFFFAOYSA-N acetic acid;1,3-diaminopropan-2-ol Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCC(O)CN CKJBFEQMHZICJP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- UCAGLBKTLXCODC-UHFFFAOYSA-N carzenide Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=C1 UCAGLBKTLXCODC-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 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
-
- 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
- G03C5/305—Additives other than developers
-
- 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
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
Definitions
- This invention relates to buffers for photographic developers and to photographic developers containing them. It is well known that the development activity of a particular photographic developer is greatly influenced by the alkalinity of the developer solution. Different developing agents naturally require different levels of pH for optimum development activity. However, the rate of development for many photographic developers depends also on the stability of the pH level of the solution. Therefore, it is evident that to obtain consistent development, the pH of the developing solution should advantageously be kept constant. The pH of the developer also should advantageously be maintained at a high level to obtain a high rate of development. The pH of the developing solution is usually kept constant by the addition of a buffer. Heretofore, many available buffers in the region of pH 913 had certain defects.
- the phosphate ion for example, is one of the best available buffers in this pH re gion but it leads to the precipitation of calcium phosphate, when calcium is present in the water or chemicals used in the developing solution.
- a further object is to provide novel photographic developing solutions containing buffers.
- photographic developing solutions are maintained at a high and more constant pH level by the use of a water-soluble, non-silver halide reducing sulfonamide.
- a water-soluble, non-silver halide reducing sulfonamide can be represented by the following general formula:
- R represents an alkyl group, such as methyl, ethyl, n-propyl, isobutyl, B-hydroxyethyl, etc. (e.g., an alkyl group containing from 1 to carbon atoms), or an aryl group, such as phenyl, 0-, mand p-tolyl, p-carboxyphenyl, p-sulfophenyl, etc.
- R represents an alkylene group, such as methylene, ethylene, etc.
- In and 11 each represents a positive integer of from 1 to 2, and R represents a hydrogen atom, an alkyl group (e.g., an alkyl group as defined above for R) or an aryl group (e.g., an aryl group as defined above for R), when n is 1, and R represents an alkyl group (e.g., an alkyl group as defined above for R) or an aryl group (e.g., an aryl group as defined above for R) when nis 2.
- Example I N ethylmethanesulfonamide, C H NHSO CH was prepared from methanesulfonylchloride and ethylamine.
- methanesulfonylchloride to 500 ml. of benzene in a l-liter round-bottomed flask equipped with dropping funnel, condenser and stirrer. Cool this mixture to 0' C. in an ice bath.
- N-(B-hydroxyet-hyl)methanesulfonamide can be prepared by substituting fi-amino ethanol in place of the ethylamine indicated in Example 1.
- pcarboxybenzenesulfonamide can be prepared by reacting p-cyanobenzenesulfonylchloride with ammonia and hydrolyzing the resultant p-cyanobenzenesulfonamide.
- the p-cyanobenzenesulfonylchloride can be prepared by the reaction of cyanobenzene with sulfo-chloride.
- the water-soluble sulfonamide buffers of the present invention are intended for use with developing solutions having a pH in the range of about 9.0'130
- the developing agents used with the buffers of our invention include the well known black and white or color developing agents, such as the phenylenediamines, including the N- alkylphe-nylenediamines and N-alkyltoluenediamines as well as the p-aminophenols, such as p-aminophenol, N- methyl-p-aminophenol, etc., hydroquinone, the 3-pyrazolidones, e.g., 1-phenyl-3-pyrazolidone, etc.
- Developing compounds containing an amino group are usually used in the form of the hydrochloride or the sulfate.
- the amount of these water-soluble sulfonamides to be added to the developing solution will vary somewhat depending-upon the particular developing agent employed and amounts of other ingredients present. In general, we have found that from about .1 to about 200 g. of the buffer per liter of the developing solution is suitable for the purpose of our invention, with a preferred range of from about 1 to about 100 g. of the buffer per liter of the developing solution.
- the usual addenda can be employed in the developers, such as restrainers (such as potassium bromide), stain preventives, such as alkali metal sulfites, sequestering agents, such as ethylenediamine tetracetic acid, 1,3-diamino-2-propanol tetracetic acid, tetrasodium salt, etc.
- restrainers such as potassium bromide
- stain preventives such as alkali metal sulfites
- sequestering agents such as ethylenediamine tetracetic acid, 1,3-diamino-2-propanol tetracetic acid, tetrasodium salt, etc.
- Example 2 a multilayer color film of the type described in Tong U.S. Patent 2,772,163, was exposed on an intensity scale sensitometer (Kodak Type 1b) and developed for minutes at 68 F. in conventional developers containing conventional buffers. Additional test films were similarly exposed and developed in the same conventional developer, but with the conventional buffer replaced by a water-soluble sulfonamide butter.
- Kodak Type 1b intensity scale sensitometer
- Example 2 This example illustrates the use of N-ethylmethanesulfonamide in a color developer of the following composition:
- the regular buffering agent Na PO 12H O and the development accelerator ethylenediamine were replaced by N-ethylmethanesulfonamide.
- the densities of blue D indicating the yellow dye yields which are critical for this type film and development, for film developed in these developers were 3.90 for the conventional developer and 3.95 for the modified developer.
- the N-ethylmethanesulfonamide buffered developer also avoids what might be a serious dirt problem.
- the phosphate ion will precipitate insoluble calcium phosphate when hard water is used to make the developer, while the calcium salt of the sulfonamide is soluble.
- the buffer capacities of the phosphate and N-ethylmethanesulfonamide are compared in Table I below.
- the buffer capacity is defined as dpH where dA is a differential addition of an acid to the developer and dpH is the change in pH resulting thereby.
- Example 3 This example compares the use of methanesulfonamide with the regularly used sodium carbonate buffer in a developer of the following formula:
- the color-forming compounds can be incorporated in the photographic emulsions, as shown in Tong U. S. Patent 2,772,163. Typical color-forming compounds which are primarily useful for use in photographic emulsions are described in Spath U.S. Patent 2,860,976.
- the buffers of our invention can also be used in color photographic processes where the color couplers are contained in the developing compositions. Typical examples of couplers which are suitable for use in color developers are described in Schwan et a1. U.S. Patent 3,068,097.
- a photographic developer composition containing a photographic silver halide developing agent and a watersoluble, non-silver halide reducing sulfonamide buffer.
- a photographic developer composition containing a photographic silver halide developing agent and a watersoluble, non-silver halide reducing sulfonamide buffer of the following formula:
- R represents an alkylene group
- R represents a member selected from the class consisting of an alkyl group and an aryl group
- R when n is 1, represents a member selected from the class consisting of a hydrogen atom, an alkyl group and an aryl group
- R when n is 2 represents a member selected from the class consisting of an alkyl group and an aryl group.
- a photographic developer composition containing a photographic silver halide developing agent and a water soluble, non-silver halide reducing sulfonamide buffer of the following formula:
- a photographic developer composition containing a photographic silver halide developing agent and a watersoluble, non-silver halide reducing sulfonamide buffer of the following formula:
- R and R each represents a member selected from the class consisting of an alkyl group and an aryl group.
- a photographic developer composition containing a photographic silver halide developing agent and a watersoluble, non-silver halide reducing sulfonamide buffer of the following formula:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE652532D BE652532A (enrdf_load_stackoverflow) | 1963-09-03 | ||
| US306304A US3305364A (en) | 1963-09-03 | 1963-09-03 | Non-silver halide reducing sulfonamide buffers for photographic developing solutions |
| DE19641447645 DE1447645A1 (de) | 1963-09-03 | 1964-07-25 | Photographischer Entwickler |
| FR986771A FR1406295A (fr) | 1963-09-03 | 1964-09-01 | Nouveau révélateur photographique |
| GB35874/64A GB1085647A (en) | 1963-09-03 | 1964-09-02 | Photographic processing solutions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US306304A US3305364A (en) | 1963-09-03 | 1963-09-03 | Non-silver halide reducing sulfonamide buffers for photographic developing solutions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3305364A true US3305364A (en) | 1967-02-21 |
Family
ID=23184709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US306304A Expired - Lifetime US3305364A (en) | 1963-09-03 | 1963-09-03 | Non-silver halide reducing sulfonamide buffers for photographic developing solutions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3305364A (enrdf_load_stackoverflow) |
| BE (1) | BE652532A (enrdf_load_stackoverflow) |
| DE (1) | DE1447645A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1085647A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647462A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films (b) |
| US3647461A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films |
| US4590154A (en) * | 1984-05-04 | 1986-05-20 | Fuji Photo Film Co., Ltd. | Heat developable color photographic light-sensitive material containing sulfonamide |
| US5063141A (en) * | 1989-04-10 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Method of processing silver halide photosensitive material |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2374921A (en) * | 1941-08-18 | 1945-05-01 | E J Gray And Arthur M Smith | Photographic developer |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2566271A (en) * | 1947-05-23 | 1951-08-28 | Eastman Kodak Co | Photographic developer containing substituted sulfonamide groups |
-
0
- BE BE652532D patent/BE652532A/xx unknown
-
1963
- 1963-09-03 US US306304A patent/US3305364A/en not_active Expired - Lifetime
-
1964
- 1964-07-25 DE DE19641447645 patent/DE1447645A1/de not_active Withdrawn
- 1964-09-02 GB GB35874/64A patent/GB1085647A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2374921A (en) * | 1941-08-18 | 1945-05-01 | E J Gray And Arthur M Smith | Photographic developer |
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
| US2566271A (en) * | 1947-05-23 | 1951-08-28 | Eastman Kodak Co | Photographic developer containing substituted sulfonamide groups |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3647462A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films (b) |
| US3647461A (en) * | 1969-02-19 | 1972-03-07 | Eastman Kodak Co | Methods and materials for replenishment of developers for color photographic films |
| US4590154A (en) * | 1984-05-04 | 1986-05-20 | Fuji Photo Film Co., Ltd. | Heat developable color photographic light-sensitive material containing sulfonamide |
| US5063141A (en) * | 1989-04-10 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Method of processing silver halide photosensitive material |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1085647A (en) | 1967-10-04 |
| DE1447645A1 (de) | 1969-02-13 |
| BE652532A (enrdf_load_stackoverflow) | 1964-12-16 |
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