US3244522A - Fog reduction in photographic silver halide emulsions - Google Patents
Fog reduction in photographic silver halide emulsions Download PDFInfo
- Publication number
- US3244522A US3244522A US226474A US22647462A US3244522A US 3244522 A US3244522 A US 3244522A US 226474 A US226474 A US 226474A US 22647462 A US22647462 A US 22647462A US 3244522 A US3244522 A US 3244522A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- xylene
- fog
- emulsion
- emulsions
- 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 36
- -1 silver halide Chemical class 0.000 title claims description 26
- 229910052709 silver Inorganic materials 0.000 title claims description 20
- 239000004332 silver Substances 0.000 title claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000005070 ripening Effects 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Chemical group 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- KFFISPTWPUGQCY-UHFFFAOYSA-N 1,4-xylene;hydrobromide Chemical compound Br.CC1=CC=C(C)C=C1 KFFISPTWPUGQCY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FDOUWHBJZXPWQS-UHFFFAOYSA-N CCC1=C(CC)C=CC=C1.Br Chemical compound CCC1=C(CC)C=CC=C1.Br FDOUWHBJZXPWQS-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
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229940074411 xylene Drugs 0.000 description 2
- VFVPMPQBPLUXLV-UHFFFAOYSA-N 1,2-xylene hydrobromide Chemical compound Br.CC1=CC=CC=C1C VFVPMPQBPLUXLV-UHFFFAOYSA-N 0.000 description 1
- QVLGWXJOCVZVJN-UHFFFAOYSA-N 1,3-xylene;hydrobromide Chemical compound Br.CC1=CC=CC(C)=C1 QVLGWXJOCVZVJN-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
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000000084 colloidal system Substances 0.000 description 1
- 150000005195 diethylbenzenes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 235000010267 sodium hydrogen 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
- 230000000087 stabilizing effect Effects 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
- Fog is caused in a number of ways, e.g., by prolonged ripening of the emulsions during storage of the film or paper, particularly at elevated temperature and humidity, or by the use of chemical sensitizers, particularly alkylene oxide derivatives, as described in United States Patents 2,704,716, 2,716,062 and 2,728,666. Prolonged developing time may also cause fogging.
- An object of our invention is to provide stabilizers or fog inhibiting agents which tend to prevent the formation of chemical fog in lightsensitive silver halides.
- a further object is to provide stabilizers or anti-fogging agents for light-sensitive silver halide emulsions which do not appreciably lower the sensitivity of the emulsions.
- a still further object is to provide stabilizers or antifogging agents for light-sensitive silver halide emulsions which do not reduce the sensitivity to light of longer wave lengths eifected by the presence of sensitizing dyes.
- R is methyl, ethyl, methyl mercapto or ethyl mercapto and R is methylene or ethylene, the alkylene value for R always being the same as the alkylene value for R and the R'SH group being in a position 0-, mor pto the R group.
- the ether is evaporated to leave an" oil which is treated with diluted sodium hydroxide.
- the alkaline solution is filtered to remove unwanted products, the filtrate acidified with dilute sulfuric acid and the mercaptan extracted with ether.
- the ether is evaporated and the oily products distilled under vacuum.
- a,a-dimercapto-o-xyl ene is prepared in the same manner excepting that o-xylene bromide is substituted for the p-xylene bromide.
- a-mercapto xylenes are also prepared in a similar fashion but by using one equivalent of KSH rather than two, as in the preparations previously described.
- the diethyl benzene derivatives are prepared in a like manner excepting that the xylene bromide is replaced by diethyl benzene. If dimercapto derivatives of the diethyl benzene are desired two equivalents of KSH are used per one equivalent of diethyl benzene bromide. If the monomercapto derivative is desired, then equal molar quantities of KSH and diethyl benzene bromide are employed.
- Beneficial effects in fog reduction may be obtained with solutions of the above compounds incorporated in the silver halide emulsions as ripening finals or as coating finals.
- Ripening finals are added during the ripening or the sensitivity stage of the emulsion making process. Such additions may be effected before, during or after the addition of a soluble silver salt to the soluble halide in the presence of a soluble photographic colloid, such as gelatin, PVA, PVP, solubilized casein or albumin.
- Coating finals are added to the emulsion just prior to coating it on a suitable support, i.e., glass, paper or film when the emulsion has nearly obtained its maximum sensitivity.
- our anti-foggants or stabilizers When used as ripening finals our anti-foggants or stabilizers are best used in a concentration of .02 to milligrams per .6 mole of silver halide and when used as coating finals in a concentration of 1 to 20 milligrams per .6 mole of silver halide. In many emulsions we prefer to apply our anti-foggants or stabilizers in a gelatin surface coating for maximum effectiveness. The concentration used depends very much on the type of emulsion employed and it is advisable to determine the optimum concentration from case to case.
- the anti-foggants and stabilizers may be employed in various types of photographic emulsions, e.g., non-sensitized, orthochromatic, panchromatic, X-ray emulsions, paper emulsions and color emulsions. They may be used in combination with other known anti-foggants or stabilizers or in combination with sulfur-, reductionmetal-and noble metal sensitizers, or in combination with polyoxyalkylenes and their derivatives.
- Example I A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating and finals were added such as sensitizing dyes and hardening agents. A 0.01% solution of a,a-dimercapto para-xylene was added to the emulsion as an anti-foggant and stabilizer. The emulsion samples contained about 0.6 mole of silver halide. The so prepared emulsion samples were coated on a cellulose ester base and dried. Samples of these film coatings were then exposed in a Type 18 sensitometer and developed in a developer of the following composition:
- Example 11 The procedure is the same as in Example I excepting that there is added fifl-dimercapto-p-dietliyl benzene in lieu of the p-xylene derivative. The results are substantially the same.
- Example III Exposed samples of a photographic film were developed for twelve minutes at 65 F. in a standard metol-hydroquinone developer. Two tests were made, one with a developer containing 4 mg. of a,a'-dimercapto para-xylene per one liter of developer. Sensitometric strips, developed in the normal developer (control) for twelve minutes showed a fog of .30, whereas those strips, which were developed in the developer containing the antifoggant, had a fog of .18.
- Example IV A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide was coated on film base in a manner known to the art. After the coating, an aqueous gelatin solution containing 20 grams of gelatin in 1 liter of H 0 and 8 mg. of e,a-dimercapto para-xylene was coated thereon as an antiabrasion layer. After drying, film samples were exposed and processed as described in Example I. The samples exhibited a relative speed of 100 and a fog of .18 compared with type coating of the above emulsion having an antiabrasion layer similar to that described above, but lacking the antifoggant and having a speed of 100 and a fog of .30.
- Example V The procedure is the same as in Example I except that the p-xylene derivative thereof is replaced by an equivalent quantity of a-mercapto-p-xylene. sults are obtained.
- Example VI wherein R is selected from the class consisting of methyl, ethyl, methyl mercapto, and ethyl mercapto and R is selected from the class consisting of methylene and ethylene, the alkylene value for R always being the same as the alkylene value for R and the RSH group being in a position selected from the class consisting of the o-, 111- and p-positions to the R group.
- a process of reducing the tendency of an exposed photographic silver halide emulsion to fog on development which comprises developing said emulsion with a developer containing a compound of the following formula:
- R is selected from the class consisting of methyl, ethyl, methyl mercapto and ethyl mercapto and R is selected from the class consisting of methylene and ethylene, the alkylene value for R always being the same as the alkylene value for R and the RSH group being in a position selected from the class consisting of the 0-, mand p-positions to the R group.
- a process of reducing the tendency of a photographic silver halide emulsion to fog on development which comprises exposing the emulsion and developing it in a metol-hydroquinone developer containing a small amount of a,ot-dimercapto-p-xylene.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE637361D BE637361A (en, 2012) | 1962-09-26 | ||
| US226474A US3244522A (en) | 1962-09-26 | 1962-09-26 | Fog reduction in photographic silver halide emulsions |
| GB34743/63A GB1049755A (en) | 1962-09-26 | 1963-09-03 | Improvements in or relating to photographic silver halide emulsions |
| DEG38654A DE1294189B (de) | 1962-09-26 | 1963-09-11 | Gegen Schleierbildung stabilisiertes photographisches Aufzeichnungsmaterial und photographischer Entwickler mit einem Antischleiermittel |
| FR948681A FR1408707A (fr) | 1962-09-26 | 1963-09-25 | Diminution du voile dans les émulsions photographiques d'halogénures d'argent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US226474A US3244522A (en) | 1962-09-26 | 1962-09-26 | Fog reduction in photographic silver halide emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3244522A true US3244522A (en) | 1966-04-05 |
Family
ID=22849041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US226474A Expired - Lifetime US3244522A (en) | 1962-09-26 | 1962-09-26 | Fog reduction in photographic silver halide emulsions |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3244522A (en, 2012) |
| BE (1) | BE637361A (en, 2012) |
| DE (1) | DE1294189B (en, 2012) |
| GB (1) | GB1049755A (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507658A (en) * | 1967-03-08 | 1970-04-21 | Gaf Corp | Thio and dithiocinnamic acids as antifoggants and stabilizers |
| US3650760A (en) * | 1969-09-17 | 1972-03-21 | Eastman Kodak Co | Alkoxy mercaptophenols as photographic addenda for photographic elements |
| DE3345023A1 (de) * | 1982-12-17 | 1984-06-20 | Fuji Photo Film Co., Ltd., Minami Ashigara, Kanagawa | Waermeentwickelbares farbphotographisches material |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6079348A (ja) * | 1983-10-06 | 1985-05-07 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956876A (en) * | 1957-09-09 | 1960-10-18 | Eastman Kodak Co | Mercapto heterocyclic addenda for reversal color development |
| US3008829A (en) * | 1960-04-11 | 1961-11-14 | Gen Aniline & Film Corp | Photographic materials and method of producing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957183C (de) * | 1953-07-01 | 1957-01-31 | Eastman Kodak Co | Stabilisiertes photographisches Material |
-
0
- BE BE637361D patent/BE637361A/xx unknown
-
1962
- 1962-09-26 US US226474A patent/US3244522A/en not_active Expired - Lifetime
-
1963
- 1963-09-03 GB GB34743/63A patent/GB1049755A/en not_active Expired
- 1963-09-11 DE DEG38654A patent/DE1294189B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956876A (en) * | 1957-09-09 | 1960-10-18 | Eastman Kodak Co | Mercapto heterocyclic addenda for reversal color development |
| US3008829A (en) * | 1960-04-11 | 1961-11-14 | Gen Aniline & Film Corp | Photographic materials and method of producing the same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507658A (en) * | 1967-03-08 | 1970-04-21 | Gaf Corp | Thio and dithiocinnamic acids as antifoggants and stabilizers |
| US3650760A (en) * | 1969-09-17 | 1972-03-21 | Eastman Kodak Co | Alkoxy mercaptophenols as photographic addenda for photographic elements |
| DE3345023A1 (de) * | 1982-12-17 | 1984-06-20 | Fuji Photo Film Co., Ltd., Minami Ashigara, Kanagawa | Waermeentwickelbares farbphotographisches material |
| US4614702A (en) * | 1982-12-17 | 1986-09-30 | Fuji Photo Film Co., Ltd. | Heat-developable color photographic material with mercapto antifoggant |
Also Published As
| Publication number | Publication date |
|---|---|
| BE637361A (en, 2012) | |
| DE1294189B (de) | 1969-04-30 |
| GB1049755A (en) | 1966-11-30 |
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