US3671255A - Silver halide emulsion fog inhibited with quaternary ammonium,triazole and tetrazaindene compounds - Google Patents
Silver halide emulsion fog inhibited with quaternary ammonium,triazole and tetrazaindene compounds Download PDFInfo
- Publication number
- US3671255A US3671255A US66141A US3671255DA US3671255A US 3671255 A US3671255 A US 3671255A US 66141 A US66141 A US 66141A US 3671255D A US3671255D A US 3671255DA US 3671255 A US3671255 A US 3671255A
- Authority
- US
- United States
- Prior art keywords
- compounds
- group
- compound
- silver halide
- alkyl
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 70
- -1 Silver halide Chemical class 0.000 title abstract description 18
- 229910052709 silver Inorganic materials 0.000 title abstract description 15
- 239000004332 silver Substances 0.000 title abstract description 15
- 239000000839 emulsion Substances 0.000 title description 15
- 150000003852 triazoles Chemical class 0.000 title description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 title 1
- 239000000463 material Substances 0.000 abstract description 22
- ZUIVNYGZFPOXFW-UHFFFAOYSA-N chembl1717603 Chemical compound N1=C(C)C=C(O)N2N=CN=C21 ZUIVNYGZFPOXFW-UHFFFAOYSA-N 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 150000001450 anions Chemical group 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical group 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 206010070834 Sensitisation Diseases 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000008313 sensitization Effects 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000005070 ripening Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 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
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-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
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- LROUPBJRCFXQIH-UHFFFAOYSA-N 5-methyl-1h-[1,2,4]triazolo[1,5-a]pyrimidin-2-one Chemical compound N1=C(C)C=CN2NC(=O)N=C21 LROUPBJRCFXQIH-UHFFFAOYSA-N 0.000 description 1
- 101100455877 Caenorhabditis elegans misc-1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- 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
Definitions
- a light-sensitive silver halide photographic material especially suited for quick development, contains as antifoggants at least one of the compounds represented by the general Formulas I, II, III and IV wherein R and R are individually an alkyl or hydroxyalkyl group having 1 to 18 carbon atoms; R is an alkyl or hydroxyalkyl group having 1 to 18 carbon atoms, or an aryl or aralkyl group; Z is a non-metallic atomic group necessary for formation of hetero ring by bonding to the nitrogen atom; A is an alkyl, alkenyl, aryl or aralkyl group; B is CH O (CH OCH war-Gen,
- n is a positive integer of 1 to and X is an anion, combined with 4-hydroxy-6-methyl-1,3,3a,7-tetrazaindene in at least one layer of the photographic material.
- Y is a hydrogen atom, a nitro group, a halogen atom or a methyl group, is further incorporated as third component.
- the present invention relates to light-sensitive silver halide photographic materials containing as antifoggants compounds represented by the general Formulas I, II, III and IV shown later in combination with 4-hydroxy- 6-methyl-1,3,3a,7-tetrazaindene. Further, the present invention involves use of a benzotriazole derivative of the general Formula V as additional ingredient.
- the object of the invention is to provide light-sensitive silver halide photographic materials excellent in anti-fogging property, particularly those which, at the time of quick development, display excellent anti-fogging property and are less in variation of photographic properties as compared with the case of ordinary development.
- light-sensitive photographic materials have been sensitized according to various sensitization methods such as sulfur sensitization, reduction sensitization, noble metal sensitization, polyalkylene glycol sensitization, etc.
- sensitization methods such as sulfur sensitization, reduction sensitization, noble metal sensitization, polyalkylene glycol sensitization, etc.
- the above-mentioned sensitization methods have a tendency to deteriorate the fog characteristics of the photographic materials, so that anti-foggants have ordinarily been used.
- anti-foggants there have been known a large number of compounds. Particularly typical among these compounds are 4-hydroxy-6-methyl- 1,3,3a,7-tetrazaindene and 1-phenyl-S-mercaptotetrazole.
- the former compound has an action to inhibit a silver halide emulsion from formation of fog during storage, and is relatively low in anti-fogging effect on an emulsion immediately after preparation.
- the latter compound has an action to inhibit a silver halide emulsion from formation of fog immediately after preparation.
- the said two compounds are used in combination to accomplish the inhibition of fogging.
- the compounds represented by the general Formulas I to IV have been known as sensitizers, as set forth in United States Pat. 2,288,226 and other literature, and scarcely show anti-fogging effects.
- the compound represented by the general Formula V has been known as an anti-foggant, but is strong in desensitizing action, like in the case of 1-phenyl-5-mercaptotetrazole, and when used in an amount capable of displaying a sufficient anti-fogging effect at the time of high temperature development, it is too strong in desensitizing action to be suitable for practical purpose.
- the compounds are formed, either singly or in admixture, into aqueous solutions, alkali solutions or alcohol solutions, and then added to the emulsion.
- the amounts of the compounds to be added are preferably such that per g.
- the amount of the 4-hydroXy6-methyl- 1,3,3a,7-tetrazaindene is 0.05 to 6.0 g.
- the amount of the compound represented by any of the general Formulas I to 'IV is less than 1 g.
- the amount of the compound represented by the general Formula V if used is less than 0.3 g.
- the compounds may be added to any one of the layers constituting the light-sensitive photographic material such as protective layer, inter layer, filter layer, etc. In this case also, the amounts of the compounds to be added are within the above-mentioned ranges. Further, the compounds may be used in combination with dyes, sensitizers, hardeners and the like known photographic additives.
- EXAMPLE 1 A geltine emulsion of 60 g. of silver iodobromide containing 1.5 mole percent of silver iodide was subjected at the time of second ripening to gold sensitization. After completion of the ripening, the emulsion was equally divided into several portions. One portion was used as a control, and the remaining portions were incorporated with such compounds as shown in Table 1. Subsequently, these emulsions were individually coated on a polyester film base and then dried to prepare samples. The samples were treated according to the sensitometry described in JIS-K-7604, and photographic properties of the treated samples were measured to obtain the results set forth in Table 1. Development was effected under such conditions as shown in Table 1, using developers of the following compositions:
- the Compound A is 4-hydroxy-6-methyl- In Table 2, the Developers I and II and the Compounds 1,3,3a,7-tetrazaindene, and the Compound B is l-phenyl- S-mercaptotetrazole.
- EXAMPLE 2 An emulsion prepared in the same manner as in Example 1 was equally divided into several portions. One portion was used as a control, and the remaining portions were incorporated with such compounds as shown in Table 2. Subsequently, these emulsions were individually coated on a cellulose triacetate film base and then dried to prepare samples. The samples were treated in the same manner as in Example 1 to obtain the results set forth in Table 2.
- xemp e oompoun Compoun (A) 750 85 81 Exemphfied compound (6)... 40 Exemplified compound (2 20 0. 05 71 0. 05 76 gompolugddMt) 5&6. 750 xemp e compoun 20 Compound (A) 750 51 49 TABLE 3 Developer (I) Developer (11) 40 0., 30 sec. 20 0., 4.5 min: Amount added Relative Relative (mg.) Fog speed Fog speed Control 0. 30 100 0. 0s s2 0. 26 98 0. 06 80 Compound (B)..
- EXAMPLE 4 A gelatine emulsion of 60 g. of silver iodobromide containing 5.3 mole percent of silver iodide was subjected at the time of second ripening to gold sensitization. After completion of the ripening, the emulsion was equally divided into several portions. One portion was used as a control, and the remaining portions were incorporated with such compounds as shown in Table 4. Subsequentl, these emulsions were individually coated on a cellulose triacetate film base and then dried to prepare samples. The samples were treated in the same manner as in or hydroxyalkyl group having 1 to 18 carbon atoms, or
- A is an alkyl, alkenyl, aryl or aralkyl group
- B is amQwmanion, combined with 4-hydroxy-6-methyl-l,3,3a,7-tetrazaindene and a compound of the general formula where Y is a hydrogen atom, a nitro group, a halogen Example 1 to obtain the results set forth in Table 4. atom or amethyl group.
- a light-sensitive silver halide photographic material especially suited for quick development, which contains in at least one layer of the photographic material, as antifoggant: at least one compound represented by the general Formulae I, II, III and IV wherein R and R are individually an alkyl or hydroxyalkyl group having 1 to 18 carbon atoms; R is an alkyl and 4-hydroXy-6-methyl-1,3,3a,7-tetrazaindene.
- a light-sensitive silver halide photographic material as claimed in claim 1, wherein the antifoggant used is the combination of the following three:
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 |
|---|---|---|---|
| JP44067624A JPS4834167B1 (enrdf_load_stackoverflow) | 1969-08-28 | 1969-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3671255A true US3671255A (en) | 1972-06-20 |
Family
ID=13350304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US66141A Expired - Lifetime US3671255A (en) | 1969-08-28 | 1970-08-21 | Silver halide emulsion fog inhibited with quaternary ammonium,triazole and tetrazaindene compounds |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3671255A (enrdf_load_stackoverflow) |
| JP (1) | JPS4834167B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2040876A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1297553A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4030927A (en) * | 1975-01-16 | 1977-06-21 | Fuji Photo Film Co., Ltd. | Supersensitizing combinations of halogen substituted benzotriazoles and cyanine dyes |
| US4095982A (en) * | 1975-10-24 | 1978-06-20 | Fuji Photo Film Co., Ltd. | Method of developing a silver halide photographic light-sensitive material |
| US4552834A (en) * | 1984-08-06 | 1985-11-12 | Eastman Kodak Company | Enhanced bleaching of photographic elements containing silver halide and adsorbed dye |
| US4572892A (en) * | 1984-05-21 | 1986-02-25 | Eastman Kodak Company | Direct positive photographic elements with incorporated maximum density enhancing antifoggants |
| US6140029A (en) * | 1998-01-29 | 2000-10-31 | Eastman Kodak Company | Color photographic element containing elemental silver and nitrogen heterocycle in a non-light sensitive layer |
| US6190848B1 (en) | 1999-07-21 | 2001-02-20 | Eastman Kodak Company | Color photographic element containing ballasted triazole derivative and inhibitor releasing coupler |
| US6309811B2 (en) | 1999-07-21 | 2001-10-30 | Eastman Kodak Company | Color photographic element containing nitrogen heterocycle derivative and inhibitor releasing coupler |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017271A (en) * | 1955-12-01 | 1962-01-16 | Eastman Kodak Co | Photographic emulsions sensitized with alkylene oxide polymers and quaternary ammonium salts |
-
1969
- 1969-08-28 JP JP44067624A patent/JPS4834167B1/ja active Pending
-
1970
- 1970-08-13 GB GB1297553D patent/GB1297553A/en not_active Expired
- 1970-08-18 DE DE19702040876 patent/DE2040876A1/de active Pending
- 1970-08-21 US US66141A patent/US3671255A/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4030927A (en) * | 1975-01-16 | 1977-06-21 | Fuji Photo Film Co., Ltd. | Supersensitizing combinations of halogen substituted benzotriazoles and cyanine dyes |
| US4095982A (en) * | 1975-10-24 | 1978-06-20 | Fuji Photo Film Co., Ltd. | Method of developing a silver halide photographic light-sensitive material |
| US4572892A (en) * | 1984-05-21 | 1986-02-25 | Eastman Kodak Company | Direct positive photographic elements with incorporated maximum density enhancing antifoggants |
| US4552834A (en) * | 1984-08-06 | 1985-11-12 | Eastman Kodak Company | Enhanced bleaching of photographic elements containing silver halide and adsorbed dye |
| US6140029A (en) * | 1998-01-29 | 2000-10-31 | Eastman Kodak Company | Color photographic element containing elemental silver and nitrogen heterocycle in a non-light sensitive layer |
| US6190848B1 (en) | 1999-07-21 | 2001-02-20 | Eastman Kodak Company | Color photographic element containing ballasted triazole derivative and inhibitor releasing coupler |
| US6309811B2 (en) | 1999-07-21 | 2001-10-30 | Eastman Kodak Company | Color photographic element containing nitrogen heterocycle derivative and inhibitor releasing coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2040876A1 (de) | 1971-03-04 |
| JPS4834167B1 (enrdf_load_stackoverflow) | 1973-10-19 |
| GB1297553A (enrdf_load_stackoverflow) | 1972-11-22 |
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