US3409437A - Silver halide emulsions containing antibronzing agents - Google Patents
Silver halide emulsions containing antibronzing agents Download PDFInfo
- Publication number
- US3409437A US3409437A US435710A US43571065A US3409437A US 3409437 A US3409437 A US 3409437A US 435710 A US435710 A US 435710A US 43571065 A US43571065 A US 43571065A US 3409437 A US3409437 A US 3409437A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- diphenyldisulfide
- dicarboxylic acid
- emulsion
- antibronzing
- 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 description 51
- 229910052709 silver Inorganic materials 0.000 title description 41
- 239000004332 silver Substances 0.000 title description 41
- -1 Silver halide Chemical class 0.000 title description 40
- 239000003795 chemical substances by application Substances 0.000 title description 28
- 239000002253 acid Substances 0.000 description 15
- 108010010803 Gelatin Proteins 0.000 description 13
- 229920000159 gelatin Polymers 0.000 description 13
- 239000008273 gelatin Substances 0.000 description 13
- 235000019322 gelatine Nutrition 0.000 description 13
- 235000011852 gelatine desserts Nutrition 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000005070 ripening Effects 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 230000001235 sensitizing effect Effects 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- ZRWICZHXYMHBDP-UHFFFAOYSA-N 2-chlorosulfonylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(Cl)(=O)=O ZRWICZHXYMHBDP-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur 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
- 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
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/13—Antibronze agent or process
Definitions
- This invention relates to light-sensitive silver halide emulsions containing either diphenyldisulfide-3,3'-dicarboxylic acid or diphenyldisulfide-4,4'-dicarboxylic acid antibronzing agents. More particularly, this invention relates to light-sensitive gelatino silver halide emulsions containing diphenyldisulfide-3,3-dicarboxylic acid or diphenyldisulfide-4,4-dicarboxylic acid antibronzing agents.
- the object of this invention is to provide suitable antibronzing agents which do not reduce the sensitivity of silver halide emulsions or tend to dissolve in the processing solutions changing the development rate of developing solutions.
- diphenyldisulfide-3,3'-dicarboxylic acid and diphenyldisulfide-4,4'-dicarboxylic acid are excellent antibronzing agents having all of the above desirable properties.
- the diphenyldisulfide- 3,3dicarboxylic acid is considered to be more effective.
- the diphenyldisulfide-2,2'-dicarboxylic acid is unsuitable for use in our invention. This is apparently due to the higher solubility of the diphenyldisulfide-2,2- dicarboxylic acid whch makes it virtually impossible to incorporate a sufficient concentration of antibronzing agent into the silver halide emulsion.
- diphenyldisulfide-3,3- dicarboxylic acid, diphenyldisulfide-2,2'-dicarboxylic acid, diphenyldisulfide-4,4'-dicarboxylic acid are all useful as antifogging agents.
- diphenyldisulfidedicarboxylic acids are used in a concentration of .02 to 20 mg. per 0.6 gram moles of silver halide (i.e., 0.33 to 33.3 mg. per mole of silver halide).
- diphenyldisulfide-3,3-dicarboxylic acid and diphenyldisulfide-4,4'-dicarboxylic acid must be used in substantially greater concentrations, i.e., in the range of 0.5
- the antibronzing agents of our invention may be added to the emulsion at any stage during its production. Thus, they may be added as a ripening final or as a coating final. When added as a ripening final, they are added during the ripening or sensitivity-increasing stage of the emulsion-making process. Such addition may be made before, during or after the addition of a soluble silver salt to the soluble halide in the presence of a suitable colloid, such as gelatin the coloid of choice), polyvinyl alcohol, solubilized casein, albumin, etc.
- the antibronzing agents of this invention are added to the emulsion just prior to coating it on a suitable support, such as paper or film, at a time when the emulsion has nearly attained its maximum sensitivity. If desired, the antibronzing agents can be added to the adjacent layer, such as an antiabrasion gelatin layer.
- the emulsion may be optically or chemically sensitized.
- chemically sensitized we mean to include sulfur sensitizing, reduction sensitizing, metal sensitizing, etc.
- polyalkylene oxides and derivatives thereof may also be added to the emulsionfAdditional colloid material, such as PVP which serves to improve the covering power of the emulsion, may be employed.
- Various stabfizers, such as 7-hydroxy-5-alkyl-5-triazole (2,3-a) pyrimidines or antifoggants, such as phenyl-mercaptotetrazole may be employed.
- the diphenyldisulfide-3,3-dicarboxylic acid can be prepared by adding zinc dust in small portions to salts of chlorosulfonylbenzoic acid in ethanolic hydrochloric acid with adequate agitation.
- a more detailed method of preparing this compound is described in the aforementioned application, Ser. No. 281,054.
- the paraisomer is described in Beilsteins Handbuch der Organischen Chemie, vol. X, page 111.
- diphenyldisulfidedicarboxylic acids of our invention are added to the colloidal carrier either in aqueous solution, such as an alkali metal salt (potassium or sodium) or from organic solution, such as dimethyl formamide, diethyl formamide, ethanol, methanol, etc.
- aqueous solution such as an alkali metal salt (potassium or sodium)
- organic solution such as dimethyl formamide, diethyl formamide, ethanol, methanol, etc.
- diphenyldisulfidedicarboxylic acids includes both the free acid and the water-soluble salts thereof.
- EXAMPLE 1 A silver halide gelatin emulsion containing 60% AgCl and 40% AgBr was prepared in the 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. One g. of diphenyldisulfide-3,3'dicarboxylic acid which had been dissolved in 8 ml. of dimethyl formamide and diluted to 20 ml. with methanol was added to the above gelatin emulsion containing one mole silver halide. The emulsion was then coated on a cellulose ester film base and dried. Samples of the film thus coated were then exposed to actinic radiation and developed in a developer having the following composition:
- EXAMPLE II A concentration series of emulsions was prepared utilizing 0.0 g., 0.05 g., 0.125 g., 0.25 g., 0.50 g. and 1.0 g. of diphenyldisulfide-4,4'-dicarboxylic acid per kilo of a silver chloro-bromide emulsion, said silver chloro-bromide emulsion containing 25 g. of silver per kilo of emulsion.
- Each of these emulsions was applied to a suitable cellu lose acetate strip in the conventional manner, exposed, developed with a developing solution utilized in Example I and ferrotyped on a hot drum.
- diphenyldisulfide-4,4-dicarboxylic acid had little, if any, improvement over the emulsion prepared without any diphenyldisulfide-4,4'-dicarboxylic acid.
- a marked improvement in the image blackness was attained during 0.125 g. of diphenyldisulfide-4,4'-dicarboxylic acid. Best results were obtained at diphenyldisulfidedicarboxylic acids concentrations of 0.25 to 0.5 g.
- diphenyldisulfide-4,4'-dicarboxylic acid per kilo of silver halide emulsion (approximately 1 to 2 grams of diphenyldisulfide 4,4 dicarboxylic acid per mole
- diphenyldisulfidedicarboxylic acids per kilo of silver halide emulsion (approximately 1 to 2 grams of diphenyldisulfide-4,4'-dicarboxylic acid per mole of silver halide).
- the emulsion containing 0.125 and 0.25 g. per kilo results in loss in emulsion speed of /2 stop.
- the emulsion had a slightly lower sensitivity (a loss of /1 stop).
- the concentration series utilized was prepared in the manner described in Example I.
- the diphenyldisulfide-4, 4-dicarboxylic acid was put in solution by suspending 0.5 g. of said compound in 100 ml. of methanol and adding sufiicient lN NaOH until the diphenyldisulfidedicarboxylic acids dissolved.
- EXAMPLE III A silver halide gelatin emulsion was prepared in the manner described in Example I without any diphenyldisulfidedicarboxylic acids and coated on a suitable acetate strip. Two-tenths percent of gelatin was prepared and 25 mg. diphenyldisulfide-3,3'-dicarboxylic acid was added to 1 liter of the 0.2% by weight gelatin solution. This gelatin solution was applied as a protective coating on top of the emulsion layer.
- a control light-sensitive element was prepared in the same manner using a gelatin top coat which did not contain the diphenyldisulfidedicarboxylic acids. The prints were then exposed to actinic radiation, developed in the developing composition utilized in Example I and ferrotyped. The prints prepared with the diphenyldisulfidedicarboxylic acids of this invention retained their black image color while prints prepared without diphenyldisulfide-3,3' dicarboxylic acid browned.
- a light-sensitive silver halide emulsion containing as an antibronzing agent a compound selected from the group consisting of diphenyldisulfide-3,3'-dicarboxylic acid and diphenyldisulfide-4,4-dicarboxylic acid wherein said antibronzing agent comprises at least 0.5 gr. per mole of silver halide.
- a light-sensitive photographic element comprising a base and a coating of a gelatin silver halide emulsion thereon, said emulsion containing as an antibronzing agent a compound selected from the group consisting of diphenyldisulfide-3,3'-dicarboxylic acid and diphenyldisulfide-4,4'-dicarboxylic acid wherein said antibronzing agent comprises at least 0.5 gr. per mole of silver halide.
- a light-sensitive photographic element comprising a base and a coating of a gelatin silver halide emulsion thereon, said emulsion containing as an antibronzing agent at least 0.5 gr. of diphenyldisulfide-3,3'-dicarboxylic acid per mole of silver halide.
- a light-sensitive photographic element comprising a base and a coating of a gelatin silver halide emulsion thereon, said emulsion containing as an antibronzing agent at least 0.5 gr. of diphenyldisulfide-4,4'-dicarboxylic acid per mole of silver halide.
- a light-sensitive structure comprising a base, a layer of light-senstive silver halide emulsion thereon and an adjacent layer separate from the first mentioned layer containing as an antibronzing agent a compound selected from the group consisting of diphenyldisulfide-3,3-dicarboxylic acid and diphenyldisulfide-4,4'-dicarboxylic acid, wherein said compound is present in a concentration sufiicient to provide at least 0.5 gr. of antibronzing agent per mole of silver halide.
- a process of forming photographic emulsions having reduced tendency to bronze which comprises forming an emulsion, ripening the emulsion and adding thereto an antibronzing agent selected from the group consisting of diphenyldisulfide-3,3'-dicarboxylic acid and diphenyldisulfide-4,4-dicarboxylic acid wherein said antibronzing compound comprises at least 0.5 gr. per mole of silver halide.
- a process of forming a light-senstive photographic element having reduced bronzing tendency which comprises forming a silver halide emulsion, ripening the emulsion, coating said emulsion on a base and adding to the emulsion, just prior to the coating on the base, an antibronzing agent selected from the group consisting of diphenyldisulfide-3,3'-dicarboxylic acid and diphenyldisulfide-4,4'-dicarboxylic acid wherein said antibronzing agent comprises at least .05 gr. per mole of silver halide.
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)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US435710A US3409437A (en) | 1965-02-26 | 1965-02-26 | Silver halide emulsions containing antibronzing agents |
| GB2294/66A GB1135064A (en) | 1965-02-26 | 1966-01-18 | Improvements in or relating to silver halide emulsions |
| DE19661547902 DE1547902A1 (de) | 1965-02-26 | 1966-02-09 | Lichtempfindliche photographische Zubereitung |
| BE676358D BE676358A (enrdf_load_stackoverflow) | 1965-02-26 | 1966-02-11 | |
| FR51190A FR1470123A (fr) | 1965-02-26 | 1966-02-25 | Agents anti-bronzage pour émulsions photographiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US435710A US3409437A (en) | 1965-02-26 | 1965-02-26 | Silver halide emulsions containing antibronzing agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3409437A true US3409437A (en) | 1968-11-05 |
Family
ID=23729519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US435710A Expired - Lifetime US3409437A (en) | 1965-02-26 | 1965-02-26 | Silver halide emulsions containing antibronzing agents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3409437A (enrdf_load_stackoverflow) |
| BE (1) | BE676358A (enrdf_load_stackoverflow) |
| DE (1) | DE1547902A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1135064A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2010555A1 (de) * | 1969-03-07 | 1970-09-24 | Agfa-Gevaert Ag, 5090 Leverkusen | Stabilisiertes photographisches Material |
| US3651935A (en) * | 1969-09-19 | 1972-03-28 | Prym Werke William | Package with slideable display band |
| US5219721A (en) * | 1992-04-16 | 1993-06-15 | Eastman Kodak Company | Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides |
| US5418127A (en) * | 1993-05-28 | 1995-05-23 | Eastman Kodak Company | Water-soluble disulfides in silver halide emulsions |
| EP0775936A1 (en) | 1995-11-08 | 1997-05-28 | Eastman Kodak Company | Silver halide photographic elements containing dioxide compounds as stabilizers |
| US6280922B1 (en) | 1998-12-30 | 2001-08-28 | Eastman Kodak Company | High chloride silver halide elements containing activated precursors to thiolic stabilizers |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226232A (en) * | 1963-05-16 | 1965-12-28 | Gen Aniline & Film Corp | Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid |
-
1965
- 1965-02-26 US US435710A patent/US3409437A/en not_active Expired - Lifetime
-
1966
- 1966-01-18 GB GB2294/66A patent/GB1135064A/en not_active Expired
- 1966-02-09 DE DE19661547902 patent/DE1547902A1/de active Pending
- 1966-02-11 BE BE676358D patent/BE676358A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226232A (en) * | 1963-05-16 | 1965-12-28 | Gen Aniline & Film Corp | Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2010555A1 (de) * | 1969-03-07 | 1970-09-24 | Agfa-Gevaert Ag, 5090 Leverkusen | Stabilisiertes photographisches Material |
| US3651935A (en) * | 1969-09-19 | 1972-03-28 | Prym Werke William | Package with slideable display band |
| US5219721A (en) * | 1992-04-16 | 1993-06-15 | Eastman Kodak Company | Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides |
| US5418127A (en) * | 1993-05-28 | 1995-05-23 | Eastman Kodak Company | Water-soluble disulfides in silver halide emulsions |
| EP0775936A1 (en) | 1995-11-08 | 1997-05-28 | Eastman Kodak Company | Silver halide photographic elements containing dioxide compounds as stabilizers |
| US6280922B1 (en) | 1998-12-30 | 2001-08-28 | Eastman Kodak Company | High chloride silver halide elements containing activated precursors to thiolic stabilizers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1135064A (en) | 1968-11-27 |
| DE1547902A1 (de) | 1969-12-18 |
| BE676358A (enrdf_load_stackoverflow) | 1966-06-16 |
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