US3161520A - Fog reduction in photographic silver halide emulsions - Google Patents
Fog reduction in photographic silver halide emulsions Download PDFInfo
- Publication number
- US3161520A US3161520A US243745A US24374562A US3161520A US 3161520 A US3161520 A US 3161520A US 243745 A US243745 A US 243745A US 24374562 A US24374562 A US 24374562A US 3161520 A US3161520 A US 3161520A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- emulsion
- thione
- mercaptobenzothiazole
- hydroxymethyl
- 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
- 239000000839 emulsion Substances 0.000 title claims description 50
- -1 silver halide Chemical class 0.000 title claims description 35
- 229910052709 silver Inorganic materials 0.000 title claims description 27
- 239000004332 silver Substances 0.000 title claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 4
- 229940009188 silver Drugs 0.000 description 25
- 238000000034 method Methods 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 230000005070 ripening Effects 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000000087 stabilizing effect Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- SDMPSCVFJMUEOS-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(=S)N(CO)C2=C1 SDMPSCVFJMUEOS-UHFFFAOYSA-N 0.000 description 2
- NKYDKCVZNMNZCM-UHFFFAOYSA-N 5-chloro-3h-1,3-benzothiazole-2-thione Chemical compound ClC1=CC=C2SC(S)=NC2=C1 NKYDKCVZNMNZCM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- ZKEHNZSMDNNRND-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-benzoxazole-2-thione Chemical compound C1=CC=C2OC(=S)N(CO)C2=C1 ZKEHNZSMDNNRND-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- JKBKZVCZFCJVOS-UHFFFAOYSA-N 5-chloro-3-(hydroxymethyl)-1,3-benzoxazole-2-thione Chemical group ClC1=CC=C2OC(=S)N(CO)C2=C1 JKBKZVCZFCJVOS-UHFFFAOYSA-N 0.000 description 1
- JDPITNFDYXOKRM-UHFFFAOYSA-N 5-methoxy-3h-1,3-benzothiazole-2-thione Chemical compound COC1=CC=C2SC(=S)NC2=C1 JDPITNFDYXOKRM-UHFFFAOYSA-N 0.000 description 1
- ILDUPWKUQLPLKK-UHFFFAOYSA-N 5-methyl-3h-1,3-benzothiazole-2-thione Chemical compound CC1=CC=C2SC(S)=NC2=C1 ILDUPWKUQLPLKK-UHFFFAOYSA-N 0.000 description 1
- CLHLOHAQAADLRA-UHFFFAOYSA-N 6-chloro-3h-1,3-benzothiazole-2-thione Chemical compound C1=C(Cl)C=C2SC(S)=NC2=C1 CLHLOHAQAADLRA-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CWMRFSSMSXQUJC-UHFFFAOYSA-N pyrrole-2-thione Chemical class S=C1C=CC=N1 CWMRFSSMSXQUJC-UHFFFAOYSA-N 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- This invention relates to photographic materials and to methods of preparing them. More particularly, this invention relates to light-sensitive silver halide emulsions containing as a stabilizing and antifogging agent a 3-hydroxymethylazolethione.
- an object of this invention to produce a light-sensitive emulsion which is fast, stable, has a reduced tendency to fog and has good contrast.
- a further object of this invention resides in a lightsensitive emulsion which contains a compound which stabilizes the emulsion against fogging and at the same time does not materially reduce the speed and/or the contrast of the emulsion.
- azolethiones the use of which is contemplated herein, may be represented by the following formula:
- a lower alkyl radical e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl
- a carbon group e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl; a carbon group;
- Y is an oxygen or sulfur atom.
- Such addition may be made before, during or after the addition of the soluble silver salt to the soluble halide in the presence of a suitable colloid, such as gelatin, polyvinyl alcohol, solubilized casein or albumin.
- a suitable colloid such as gelatin, polyvinyl alcohol, solubilized casein or albumin.
- antifogging agent of our invention is added to the emulsion just prior to coating it on a suitable support such as glass, paper, or film at a time when the emulsion has nearly attained its maximum sensitivity.
- the antifogging and stabilizing compounds of our invention in a separate layer such as an undercoating layer or in an antiabrasion gelatin surface. Sometimes it is desirable to incorporate the compounds in one or all processing baths or in the preand post-baths.
- the antifoggants of our invention are preferably added to the emulsion in an amount ranging from 0.1 milligram to 20 milligrams per 0.6 mol of silver halide and when used as a coating final, it is preferably added in an amount ranging from 0.5 milligram to 50 milligrams per 0.6 mol of silver halide.
- the optimum amount to be added depends primarily on the type of emulsion and should be determined individually in each case.
- the stabilizers and antifoggants of our invention may also be used in combination with known antifoggants and stabilizers.
- the antifoggants of our invention can also be used in combination with sensitizers such as sulfur, metal and reduction sensitizers as well as with speed-increasing agents and accelerators such as the reaction products of long-chain alcohols and ethylene oxide (see U.S.P. 1,970,578) and their derivatives and polyvinylpyrrolidone.
- novel antifoggants of our invention may be used with various types of photographic emulsions, such as non-sensitized orthochromatic, panchromatic and X-ray emulsions, paper emulsions and color emulsions.
- Example I A silver halide emulsion in gelatin containing 2 percent silver iodide and 98 percent silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating, finals were added such as sensitizing dyes and hardening agents. A 0.1 percent solution of 3-hydroxymethylbenzothiazole-2-thione prepared according to the method described in the Journal of the Chemical Society, 1948, page 1717, was added in varying amounts to samples of the emulsion as an antifoggant and stabilizer. Each emulsion sample contained about 0.6 mol of silver halide. The so prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these film coatings were then exposed in a Type 1113 Sensitometer and developed in a developer of the following composition:
- Example [I The procedure followed was identical to Example I, except that in place of 3-hydroxymethylbenzothiazole-Z- thione the compound used was 3-hydroxymethylbenzoxazole-2-thione prepared according to the method described in Berichte, vol. 90, page 2250.
- Example III Quantity of Compound Relative Fog at 12 Oven Fog at Used Speed Develop- 6 Development ment 10
- Example III The procedure followed was identified to Example I, but in place of 3-hydroxymethyl-benzothiazole-2-thione, the compound used was 5-chloro-3-hydroxymethyl-benzothiazole-Z-thione which had been prepared in analogy to the method described in J.C.S., 1948, 1717, except that 5- chloro-2-mercaptobenzothiazole was used as the starting material in place of Z-mercaptobenzothiazole.
- Example I was repeated except that 6-methyl-3-hydroxymethyl-benzothiazole-Z-thione was used in place of 3-hydroxymethyl-benzothiazole-Z-thione. The results obtained were essentially the same as those reported in Example I.
- R is selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy and carboxy; and Y is a member selected from the group consisting of oxygen and sulfur.
- a fight-sensitive silver halide emulsion as recited in claim 1, wherein said emulsion is a panchromatic emulsion.
- a light-sensitive photographic element comprising a base and a coating of geIat-ino-silver halide emulsion thereon, said emulsion containing as an antifogging and stabilizing agent, a compound selected from the group having the following formula:
- R is selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy; and Y is a member selected from the group consisting of oxygen and sulfur.
- a light-sensitive structure comprising a base, a layer of light-sensitive silver halide emulsion thereon, and a separate layer adjacent said first-mentioned layer containing as an antifogging and stabilizing agent compound, a compound selected from the group having the following general chemical structure;
- R is selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy and carboxyalkoxy; and Y is a member selected from the group consisting of oxygen and sulfur.
- a process of forming a photographic silver halide emulsion having a reduced tendency to fog which comprises forming the emulsion, ripening the emulsion and during said ripening adding thereto a compound selected from the group having the following general formula:
- R is selected from the group consisting of hydrogen, halogen, lower alkoxy and carboxy; and Y is a member selected from the group consisting of oxygen and sulfur.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243745A US3161520A (en) | 1962-12-11 | 1962-12-11 | Fog reduction in photographic silver halide emulsions |
| BE641098A BE641098A (https=) | 1962-12-11 | 1963-12-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243745A US3161520A (en) | 1962-12-11 | 1962-12-11 | Fog reduction in photographic silver halide emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3161520A true US3161520A (en) | 1964-12-15 |
Family
ID=22919949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US243745A Expired - Lifetime US3161520A (en) | 1962-12-11 | 1962-12-11 | Fog reduction in photographic silver halide emulsions |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3161520A (https=) |
| BE (1) | BE641098A (https=) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2210369A1 (de) * | 1971-03-04 | 1972-09-28 | Fuji Photo Film Co. Ltd., Ashigara-Kamigun, Kanagawa (Japan) | Verfahren zur Herstellung von photographischen Bildern |
| DE2263808A1 (de) * | 1971-12-28 | 1973-07-05 | Fuji Photo Film Co Ltd | Lichtempfindliches silberhalogenidmaterial |
| JPS5036979B1 (https=) * | 1971-03-04 | 1975-11-28 | ||
| JPS5284734A (en) * | 1976-10-04 | 1977-07-14 | Fuji Photo Film Co Ltd | Photographic image formation |
| US4126463A (en) * | 1976-09-14 | 1978-11-21 | Agfa-Gevaert Aktiengesellschaft | Method of stabilizing photographic silver halide emulsion layers |
| US4242429A (en) * | 1977-11-01 | 1980-12-30 | Fuji Photo Film Co., Ltd. | Method of stabilizing organic substrate materials against light |
| US4518781A (en) * | 1980-03-27 | 1985-05-21 | Rhone-Poulenc Agrochimie | Process for the preparation of 3-hydroxymethyl-6-chlorobenzoxazolone |
| US5035990A (en) * | 1989-11-28 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Radiographic elements with improved covering power |
| US5097039A (en) * | 1986-08-27 | 1992-03-17 | Ciba-Geigy Corporation | Phenolic benzothiazole derivatives and their use as corrosion inhibitors |
| US5169950A (en) * | 1986-08-27 | 1992-12-08 | Ciba-Geigy Corporation | Processes for preparing phenolic benzothiazole derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870015A (en) * | 1957-03-08 | 1959-01-20 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
| US3026201A (en) * | 1959-02-02 | 1962-03-20 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
-
1962
- 1962-12-11 US US243745A patent/US3161520A/en not_active Expired - Lifetime
-
1963
- 1963-12-11 BE BE641098A patent/BE641098A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870015A (en) * | 1957-03-08 | 1959-01-20 | Eastman Kodak Co | Stabilized photographic silver halide emulsions |
| US3026201A (en) * | 1959-02-02 | 1962-03-20 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2210369A1 (de) * | 1971-03-04 | 1972-09-28 | Fuji Photo Film Co. Ltd., Ashigara-Kamigun, Kanagawa (Japan) | Verfahren zur Herstellung von photographischen Bildern |
| JPS5036979B1 (https=) * | 1971-03-04 | 1975-11-28 | ||
| DE2263808A1 (de) * | 1971-12-28 | 1973-07-05 | Fuji Photo Film Co Ltd | Lichtempfindliches silberhalogenidmaterial |
| JPS4873135A (https=) * | 1971-12-28 | 1973-10-02 | ||
| US3895948A (en) * | 1971-12-28 | 1975-07-22 | Fuji Photo Film Co Ltd | Silver halide light-sensitive material containing a heterocyclic thione and a polyalkylene oxide |
| US4126463A (en) * | 1976-09-14 | 1978-11-21 | Agfa-Gevaert Aktiengesellschaft | Method of stabilizing photographic silver halide emulsion layers |
| JPS5284734A (en) * | 1976-10-04 | 1977-07-14 | Fuji Photo Film Co Ltd | Photographic image formation |
| US4242429A (en) * | 1977-11-01 | 1980-12-30 | Fuji Photo Film Co., Ltd. | Method of stabilizing organic substrate materials against light |
| US4518781A (en) * | 1980-03-27 | 1985-05-21 | Rhone-Poulenc Agrochimie | Process for the preparation of 3-hydroxymethyl-6-chlorobenzoxazolone |
| US5097039A (en) * | 1986-08-27 | 1992-03-17 | Ciba-Geigy Corporation | Phenolic benzothiazole derivatives and their use as corrosion inhibitors |
| US5169950A (en) * | 1986-08-27 | 1992-12-08 | Ciba-Geigy Corporation | Processes for preparing phenolic benzothiazole derivatives |
| US5035990A (en) * | 1989-11-28 | 1991-07-30 | E. I. Du Pont De Nemours And Company | Radiographic elements with improved covering power |
Also Published As
| Publication number | Publication date |
|---|---|
| BE641098A (https=) | 1964-04-01 |
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