US3647469A - Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions - Google Patents
Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions Download PDFInfo
- Publication number
- US3647469A US3647469A US886747A US3647469DA US3647469A US 3647469 A US3647469 A US 3647469A US 886747 A US886747 A US 886747A US 3647469D A US3647469D A US 3647469DA US 3647469 A US3647469 A US 3647469A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- disulfides
- stabilizers
- halide emulsions
- sensitizers
- 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 abstract description 34
- -1 silver halide Chemical class 0.000 title claims abstract description 20
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 18
- 239000004332 silver Substances 0.000 title claims abstract description 18
- 239000003381 stabilizer Substances 0.000 title description 9
- 150000002019 disulfides Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 22
- 230000005070 ripening Effects 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000000084 colloidal system Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 230000001965 increasing effect Effects 0.000 abstract description 9
- 230000000694 effects Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 5
- 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 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910021612 Silver iodide Inorganic materials 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229940045105 silver iodide Drugs 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- NCNYEGJDGNOYJX-NSCUHMNNSA-N (e)-2,3-dibromo-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Br)=C(/Br)C=O NCNYEGJDGNOYJX-NSCUHMNNSA-N 0.000 description 1
- GGZHVNZHFYCSEV-UHFFFAOYSA-N 1-Phenyl-5-mercaptotetrazole Chemical compound SC1=NN=NN1C1=CC=CC=C1 GGZHVNZHFYCSEV-UHFFFAOYSA-N 0.000 description 1
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Chemical group 0.000 description 1
- 239000000298 carbocyanine Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
- 229940099500 cystamine Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- PDMYFWLNGXIKEP-UHFFFAOYSA-K gold(3+);trithiocyanate Chemical compound [Au+3].[S-]C#N.[S-]C#N.[S-]C#N PDMYFWLNGXIKEP-UHFFFAOYSA-K 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- XCGQJCSSCTYHDV-UHFFFAOYSA-N mercury(1+);sulfane Chemical compound S.[Hg+] XCGQJCSSCTYHDV-UHFFFAOYSA-N 0.000 description 1
- PKDBSOOYVOEUQR-UHFFFAOYSA-N mucobromic acid Natural products OC1OC(=O)C(Br)=C1Br PKDBSOOYVOEUQR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 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
- 230000001603 reducing effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- G03C1/08—Sensitivity-increasing substances
- G03C1/09—Noble metals or mercury; Salts or compounds thereof; Sulfur, selenium or tellurium, or compounds thereof, e.g. for chemical sensitising
-
- 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
- ABSTRACT The present invention relates to a process for increasing the sensitivity of photographic silver halide emulsions together with reduced fogging by the addition of bis-aminoalkyl disulfides.
- the sensitivity of a photographic emulsion can be affected in two ways. First, the sensitivity can be increased during the preparation of the emulsion, at the stage of so-called chemical ripening by increasing the ripening time or by adding suitable substances such as thiosulfate or other compounds which usually contain sulfur.
- the other method of increasing the sensitivity of a photographic emulsion consists of adding so-called development accelerators or chemical sensitizers. These are usually added to the ripened emulsion.
- the compounds which have been described as development accelerators include, e.g., compounds which have an onium structure (such as quaternary ammonium and phosphonium salts and ternary sulfonium salts) and also polyalkylene oxides and polyalkylene oxide derivatives are very often employed.
- the compounds according to the invention show their advantageous effect particularly when they replace thiosulfate or other sulfur compounds in the chemical ripening.
- the considerable reduction in the fogging in the samples is very striking. This reduction in fogging can be observed not only in fresh samples but also after the samples have been stored in the heating cupboard.
- the real advantage of using compounds according to the invention lies not so much in the increase in sensitivity itself, but in the combination of increase in sensitivity together with reduction in fogging, which makes it possible to add other ingredients to the emulsion, which might possibly have the effect of increasing the fogging, without a net increase in fogging resulting.
- Emulsions prepared with the compounds according to the invention will, therefore, be particularly suitable for use in combination with other development accelerators.
- the reduced fogging will also be very important in the preparation of color emulsions since these are normally very susceptible to fogging.
- the compounds according to the invention may be added to the photographic emulsion at any stage of its preparation, i.e., before, during or after chemical ripening. They may also be added to the casting solution immediately before casting. The quantity added depends on the required effect and can be determined by those skilled in the art at any time by the usual tests.
- the compounds according to the invention may be used in any silver halide emulsions.
- Suitable silver halides are silver chloride, and silver bromide or mixtures thereof, if desired with a small silver iodide content of up to 10 mols percent.
- the silver halides may be dispersed in the usual hydrophilic compounds, for example in carboxymethylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, alginic acid and its salts, esters or amides and preferably gelatin.
- the emulsions also may contain other chemical sensitizers, e.g., quaternary ammonium and phosphonium salts and temary sulfonium salts, reducing agents such as stannous salts, polyamines such as diethylene triamine or sulfur compounds such as described in U.S. Pat No. 1,574,944.
- the above mentioned emulsions may also contain salts of noble metals such as ruthenium, rhodium, palladium, iridium, platinum or gold for chemical sensitization, as described in the article by R. Koslowsky, z. Wiss. Phot. 46, 6572 1951).
- the emulsions also may be optically sensitized, e.g., with the usual polymethine dyes such as merocyanines basic or acid carbocyanines, rhodacyanines, hemicyanines, styryl dyes, and oxonols. Sensitizers of this type are described in the book by F. M. Hamer The Cyanine Dyes and related Compounds 1964
- the emulsions may contain the usual stabilizers, e.g., homopolar or salt-type compounds of mercury with aromatic or heterocyclic rings (for example mercaptotn'azoles), simple mercury salts sulfonium mercury double salts and other mercury compounds.
- Azaindenes especially tetra or penta-azaindenes, and in particular those which are substituted with hydroxyl or amino groups, are also suitable as stabilizers.
- stabilizers Compounds of this type are described in the article by Birr. Z. Wiss. Phot. 47. 2 58 (1952).
- Other suitable stabilizers include heterocyclic mercapto compounds, e.g., phenylmercaptotetrazole, quaternary benzothiazole derivatives, and benzotriazole.
- the emulsions may be hardened in the usual manner, for example with formaldehyde or halosubstituted aldehydes which contain a carboxyl group, such as mucobromic acid, diketones, methanesulfonic acid esters, and dialdehydes.
- formaldehyde or halosubstituted aldehydes which contain a carboxyl group, such as mucobromic acid, diketones, methanesulfonic acid esters, and dialdehydes.
- the emulsions treated with bis-amino-alkyldisulfides according to the invention may also contain color couplers for the production of color photographic images.
- EXAMPLE 1 A silver iodobromide emulsion containing 5 mols percent of silver iodide is prepared in the usual manner. The pAg is adjusted to 8.9 the pH to 6.8 and the viscosity to 8 cp. for after ripening. Gold thiocyanate is then added and the emulsions is divided into four equal parts. The following additions are then made to the individual samples (based on 1 kg. of emulsion) containing g. of silver bromide with a silver iodide content of 4 mols percent:
- Sample A Comparison samplewithout additive
- Sample B 3.3 mg. of a compound of the following formula
- Sample D 3.3 mg. of a compound of the following formula (for comparison) CzHs acetate, exposed in the sensitometer behind a grey step wedge and developed at 20 C. in a developer of the following composition:
- the development time is 6 minutes.
- a difference of 3 corresponds to a sensitivity difference of oneshutter stop.
- a light sensitive photographic material having at least one silver halide emulsion layer, which contains a sensitizing amount of a compound of the following general formula:
- X is the anion of any photographically inert acid.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681816571 DE1816571A1 (de) | 1968-12-23 | 1968-12-23 | Photographische Halogensilberemulsion mit erhoehter Empfindlichkeit und vermindertemSchleier |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3647469A true US3647469A (en) | 1972-03-07 |
Family
ID=5717200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US886747A Expired - Lifetime US3647469A (en) | 1968-12-23 | 1969-12-19 | Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3647469A (enrdf_load_stackoverflow) |
| BE (1) | BE743489A (enrdf_load_stackoverflow) |
| DE (1) | DE1816571A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2026969A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1261140A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3926632A (en) * | 1971-09-13 | 1975-12-16 | Agfa Gevaert Nv | Photographic silver halide lith material |
| US4458010A (en) * | 1981-11-13 | 1984-07-03 | Fuji Photo Film Co., Ltd. | Process for bleaching color photographic sensitive materials |
| US4952488A (en) * | 1985-12-09 | 1990-08-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material and processing process therefor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2931690A1 (de) * | 1979-08-04 | 1981-02-19 | Agfa Gevaert Ag | Photographische emulsion, verfahren zur herstellung sowie photographische materialien |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438716A (en) * | 1944-10-06 | 1948-03-30 | Gen Aniline & Film Corp | Stabilized silver halide emulsions |
| US3057725A (en) * | 1959-07-17 | 1962-10-09 | Eastman Kodak Co | Substituted disulfides as antifoggants for silver halide emulsions |
-
1968
- 1968-12-23 DE DE19681816571 patent/DE1816571A1/de active Pending
-
1969
- 1969-12-19 US US886747A patent/US3647469A/en not_active Expired - Lifetime
- 1969-12-22 BE BE743489D patent/BE743489A/xx unknown
- 1969-12-23 GB GB62530/69A patent/GB1261140A/en not_active Expired
- 1969-12-23 FR FR6944656A patent/FR2026969A1/fr not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2438716A (en) * | 1944-10-06 | 1948-03-30 | Gen Aniline & Film Corp | Stabilized silver halide emulsions |
| US3057725A (en) * | 1959-07-17 | 1962-10-09 | Eastman Kodak Co | Substituted disulfides as antifoggants for silver halide emulsions |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3926632A (en) * | 1971-09-13 | 1975-12-16 | Agfa Gevaert Nv | Photographic silver halide lith material |
| US4458010A (en) * | 1981-11-13 | 1984-07-03 | Fuji Photo Film Co., Ltd. | Process for bleaching color photographic sensitive materials |
| US4952488A (en) * | 1985-12-09 | 1990-08-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material and processing process therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1816571A1 (de) | 1970-07-09 |
| GB1261140A (en) | 1972-01-19 |
| BE743489A (enrdf_load_stackoverflow) | 1970-06-22 |
| FR2026969A1 (enrdf_load_stackoverflow) | 1970-09-25 |
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| US3597213A (en) | Fog reduction in photographic silver halide emulsions | |
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