US3433640A - Photographic silver halide light-sensitive material - Google Patents
Photographic silver halide light-sensitive material Download PDFInfo
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- US3433640A US3433640A US506842A US3433640DA US3433640A US 3433640 A US3433640 A US 3433640A US 506842 A US506842 A US 506842A US 3433640D A US3433640D A US 3433640DA US 3433640 A US3433640 A US 3433640A
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- United States
- Prior art keywords
- compound
- silver halide
- sensitive material
- photographic
- silver
- 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
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- 239000000463 material Substances 0.000 title claims description 21
- 229910052709 silver Inorganic materials 0.000 title claims description 16
- 239000004332 silver Substances 0.000 title claims description 16
- -1 silver halide Chemical class 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000839 emulsion Substances 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 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
- QMJDEXCUIQJLGO-UHFFFAOYSA-N [4-(methylamino)phenyl] hydrogen sulfate Chemical compound CNC1=CC=C(OS(O)(=O)=O)C=C1 QMJDEXCUIQJLGO-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-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
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004952 Polyamide Substances 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
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film 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
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- Photographic silver halide emulsions are generally produced by dispersing crystals of silver halide such as silver iodide, bromide and chloride in gelatin, polyvinyl alcohol or other high molecular electrolytes as a protective colloid and are applied as a light-sensitive material on a support of paper, glass, nitrocellulose, acetylcellulose, polyamide, polyester, polycarbonate and other synthetic high molec ular materials in a thin film whereby photographic films, plates and papers are obtained.
- silver halide such as silver iodide, bromide and chloride
- gelatin polyvinyl alcohol or other high molecular electrolytes as a protective colloid
- the present invention is characterized by incorporating in a light sensitive material during production or with the starting materials thereof at least one of the thiazoline-Z-thiones represented by the following general formula:
- the compound may be added in a silver halide emulsion at any step, but it is preferable to add the above compound, as the crystal or as a solution, when the crys tals of silver halide are formed or ripened after washing with water, or just before the photographic silver halide emulsion is dissolved and coated on a support.
- the compound may be incorporated in, for example, an adjacent layer of the photographic silver halide emulsion layer (therefore, the term silver halide emulsion layer in the specification and claims includes the layers adjacent the emulsion layer). More particularly, if the compound contained in gelatin or other protective colloid is added during production, the dispersion thereof can be favorably eflected. Moreover, a light sensitive material may be treated with a solution containing the compound.
- the first object accomplished by our invention is to make a blue-black tone of developed silver image of a 3 light sensitive material, in particular, photographic paper or positive photographic material and the second object is to raise the sensitivity of a light sensitive material.
- Example 1 20 ml. of 0.3% methanol solution of the Compound 1 was added to 1 kg. of an adherent photographic paper emulsion containing 21.5 g. of silver chloride, to which 20 ml. of 6% aqueous solution of formalin was further added, and coated on baryta paper. The thus obtained photographic paper was exposed and developed at 20 C. for 1 minute by the use of the following developer after diluting to 1:1.
- the developing treatment After the developing treatment, it was dipped in a stop bath of 1.5% acetic acid solution for 15-20 seconds, fixed for 10 minutes in an acidic hardening fixing solution and washed with water for 60 minutes in water flow. Thereafter, the developed material was then subjected to the hot-glaze or natural drying.
- Example 2 30 ml. of 0.3% methanol solution of the Compound 2 was added to 1 kg. of an enlargement photographic paper emulsion containing 25 g. of silver chlorobromide (silver bromide 30 mol percent), coated on a support similarly to Example 1 and dried. The resulting photographic paper, being exposed similarly to Example 1, was developed for 2 minutes at 20 C., fixed and washed with water. In this photographic paper to which the Compound 2 had been added, the initial developing velocity was rapid, the sensitivity was increased by 10% and images having a blueblack tone were obtained, as compared with images having a brownish-black tone in another photographic paper to which it had not been added.
- Example 3 30 ml. of 0.3% methanol solution of the Compound 2 and 15 ml. of 0.1% aqueous solution of 1-phenyl-5- mercaptotetrazole as a fog inhibitor were added to 1 kg. of an adherent photographic paper emulsion containing 23 g. of silver chlorobromide (silver bromide 7 mol percent), coated on a support similarly to Example 1 and dried.
- the resulting photographic paper, being exposed as in Example 1 was developed at 20 C. for 1 minute 30 seconds, fixed, washed with water and dried. In this photographic paper, no fog increase was observed and an image having a blue-black tone was obtained without delaying the initial development, as compared with an image having a neutral black tone in the case of no addition of the compound.
- Example 4 When the procedure as in Example 1 was repeated using 60 ml. of a 0.3% methanol solution of Compound 4 instead of Compound 1, almost same brown-black images as in Example 1 were obtained.
- Example 5 40 ml. of 0.2% methanol solution of the Compound 6 was added to 1 kg. of a micro-positive emulsion containing 35 g. of silver chlorobromide (silver bromide 45 mol percent), coated on a triacetylcellulose film support to which a subbing layer had been previously applied, and
- Example 6 To 1 kg. of a fine grain positive emulsion containing 50 g. of silver iodobromide (silver iodide 1.5 mol percent) was added the compound of our invention as shown in Table I. The composition was coated on a triacetylcellulose film support having a subbing layer, followed by drying. The thus obtained film, after exposure, was developed at 20 C. for 5 minutes by the use of the following developer and then was fixed, washed with water and dried.
- silver iodobromide silver iodide 1.5 mol percent
- the sensitivity alone could be raised, by increasing the amount of the compound, without substantially affecting the gamma and fog.
- Example 7 To 100 g. of a photographic emulsion containing 2.8 g.
- the resulting photographic plate after exposure to light, was developed at 20 C. for 3 minutes by the developer having the following composition and was then fixed, washed with water and dried.
- a photographic silver halide sensitive material comprising a support and a silver halide emulsion layer, said layer containing at least one compound selected from the group consisting of compounds represented by the general formula:
- R represents a member selected from the class consisting of an alkyl group, a cyclo-alkyl group, an aryl group, a pyrimidylmethyl group; and R and R each represents a member selected from the class consisting of a hydrogen atom, a lower alkyl group, a hydroxyalkyl group, and an aryl group; said R and R" being linked to each other as the case may be.
- R represents an alkylene group and R and R" each represents a member selected from the class consisting of a hydrogen atom, a lower alkyl group, a hydroxyalkyl group and an aryl group, said R' and R being linked to each other as the case may be.
- a material as defined in claim 1 wherein said compound is 5.
- a material as defined in claim 1 wherein said compound is 7.
- a material as defined in claim 1 wherein said compound is /CE1 /S EH2 ⁇ C S H o N/CHz-CH:
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- 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)
- Steroid Compounds (AREA)
Description
United States Patent 39/ 63,973 US. Cl. 96-107 Claims Int. Cl. G03c 1/28 This invention relates to photographic silver halide sensitive materials and to silver halide emulsions for photographic materials.
Photographic silver halide emulsions are generally produced by dispersing crystals of silver halide such as silver iodide, bromide and chloride in gelatin, polyvinyl alcohol or other high molecular electrolytes as a protective colloid and are applied as a light-sensitive material on a support of paper, glass, nitrocellulose, acetylcellulose, polyamide, polyester, polycarbonate and other synthetic high molec ular materials in a thin film whereby photographic films, plates and papers are obtained.
We have found that the photographic characteristics can be remarkably improved by adding thiazoline-Z- thionesto such light sensitive material during production or with the starting materials.
That is to say, the present invention is characterized by incorporating in a light sensitive material during production or with the starting materials thereof at least one of the thiazoline-Z-thiones represented by the following general formula:
II HIE \es "ice Compound 2.
GNs-
Compound 3.
Compound 4.
CH Compound 5.
CH2 \C=s Compound 7.
The compound may be added in a silver halide emulsion at any step, but it is preferable to add the above compound, as the crystal or as a solution, when the crys tals of silver halide are formed or ripened after washing with water, or just before the photographic silver halide emulsion is dissolved and coated on a support. The compound may be incorporated in, for example, an adjacent layer of the photographic silver halide emulsion layer (therefore, the term silver halide emulsion layer in the specification and claims includes the layers adjacent the emulsion layer). More particularly, if the compound contained in gelatin or other protective colloid is added during production, the dispersion thereof can be favorably eflected. Moreover, a light sensitive material may be treated with a solution containing the compound.
The first object accomplished by our invention is to make a blue-black tone of developed silver image of a 3 light sensitive material, in particular, photographic paper or positive photographic material and the second object is to raise the sensitivity of a light sensitive material.
Example 1 20 ml. of 0.3% methanol solution of the Compound 1 was added to 1 kg. of an adherent photographic paper emulsion containing 21.5 g. of silver chloride, to which 20 ml. of 6% aqueous solution of formalin was further added, and coated on baryta paper. The thus obtained photographic paper was exposed and developed at 20 C. for 1 minute by the use of the following developer after diluting to 1:1.
G. N-methyl-p-aminophenol sulphate 2 Anhydrous sodium sulfite 30 Hydroquinone 7 Sodium carbonate (monohydrate) 53 Potassium bromide 1.5
Water to 1000 ml.
After the developing treatment, it was dipped in a stop bath of 1.5% acetic acid solution for 15-20 seconds, fixed for 10 minutes in an acidic hardening fixing solution and washed with water for 60 minutes in water flow. Thereafter, the developed material was then subjected to the hot-glaze or natural drying.
In carrying out this invention, images having a satisfactory blue-black tone could be obtained, while images having a brownish-black tone were obtained in the case of no addition of the compound (development, stopping fixing, water washing and drying were similar to in the former).
Example 2 30 ml. of 0.3% methanol solution of the Compound 2 was added to 1 kg. of an enlargement photographic paper emulsion containing 25 g. of silver chlorobromide (silver bromide 30 mol percent), coated on a support similarly to Example 1 and dried. The resulting photographic paper, being exposed similarly to Example 1, was developed for 2 minutes at 20 C., fixed and washed with water. In this photographic paper to which the Compound 2 had been added, the initial developing velocity was rapid, the sensitivity was increased by 10% and images having a blueblack tone were obtained, as compared with images having a brownish-black tone in another photographic paper to which it had not been added.
Example 3 30 ml. of 0.3% methanol solution of the Compound 2 and 15 ml. of 0.1% aqueous solution of 1-phenyl-5- mercaptotetrazole as a fog inhibitor were added to 1 kg. of an adherent photographic paper emulsion containing 23 g. of silver chlorobromide (silver bromide 7 mol percent), coated on a support similarly to Example 1 and dried. The resulting photographic paper, being exposed as in Example 1, was developed at 20 C. for 1 minute 30 seconds, fixed, washed with water and dried. In this photographic paper, no fog increase was observed and an image having a blue-black tone was obtained without delaying the initial development, as compared with an image having a neutral black tone in the case of no addition of the compound.
Example 4 When the procedure as in Example 1 was repeated using 60 ml. of a 0.3% methanol solution of Compound 4 instead of Compound 1, almost same brown-black images as in Example 1 were obtained.
Example 5 40 ml. of 0.2% methanol solution of the Compound 6 was added to 1 kg. of a micro-positive emulsion containing 35 g. of silver chlorobromide (silver bromide 45 mol percent), coated on a triacetylcellulose film support to which a subbing layer had been previously applied, and
dried. The film thus resulting, being exposed similarly to Example 1, was developed at 20 C. for 2 minutes, fixed, washed with Water and dried. This film gave a good image of neutral black tone, as compared with an image of brownish-black tone obtained in the case of no addition of the compound.
Example 6 To 1 kg. of a fine grain positive emulsion containing 50 g. of silver iodobromide (silver iodide 1.5 mol percent) was added the compound of our invention as shown in Table I. The composition was coated on a triacetylcellulose film support having a subbing layer, followed by drying. The thus obtained film, after exposure, was developed at 20 C. for 5 minutes by the use of the following developer and then was fixed, washed with water and dried.
G. N-methyl-p-aminophenol sulphate 0.3 Anhydrous sodium sulfite 38.0 Hydroquinone 6.0 Sodium carbonate (monohydrate) 22.5 Citric acid 0.7 Potassium bromide 0.9 Potassium metabisulfite 1.4 Water to 1000 ml.
TABLE 1 Compound Amount added Specific Gamma Fog sensitivity 0 3.1 0.05 2 6 10- 107 3. 1 0. 05 2X10 129 3. 3 0. 05 0 1o- 162 3. 5 0. 05 2X10- 200 3. 5 0. O6 3 6x10 3. 1 0. 05 2 10- 3.3 0. 05 6 10- 3. 3 0. 0s 2 1o- 230 3. 5 0. 07 5 e 10- 105 3. 1 o. 05 2 10 125 3. 1 0. 05 6X10- 150 3. 1 0. 05 2X10! 3. 3 0. 05
In the case of thus carrying out our invention, the sensitivity alone could be raised, by increasing the amount of the compound, without substantially affecting the gamma and fog.
Example 7 To 100 g. of a photographic emulsion containing 2.8 g.
of silver chloride was added a M/lOO methanol-acetone (4:1) solution of the Compound 1, 2 or 7 in an amount as shown in Table II, coated on a glass plate to be 6 ml. emulsion/ 200 cm. and dried.
The resulting photographic plate, after exposure to light, was developed at 20 C. for 3 minutes by the developer having the following composition and was then fixed, washed with water and dried.
What is claimed is:
1. A photographic silver halide sensitive material comprising a support and a silver halide emulsion layer, said layer containing at least one compound selected from the group consisting of compounds represented by the general formula:
S RC [I \C= S R1 and, a compound represented by the general formula:
wherein R represents a member selected from the class consisting of an alkyl group, a cyclo-alkyl group, an aryl group, a pyrimidylmethyl group; and R and R each represents a member selected from the class consisting of a hydrogen atom, a lower alkyl group, a hydroxyalkyl group, and an aryl group; said R and R" being linked to each other as the case may be.
3. A light-sensitive silver halide emulsion containing a compound selected from the group consisting of compounds represented by the general formula:
wherein R represents an alkylene group and R and R" each represents a member selected from the class consisting of a hydrogen atom, a lower alkyl group, a hydroxyalkyl group and an aryl group, said R' and R being linked to each other as the case may be.
4. A material as defined in claim 1 wherein said compound is 5. A material as defined in claim 1 wherein said compound is I O=s CH3- 6. A material as defined in claim 1 wherein said compound is 7. A material as defined in claim 1 wherein said compound is S S C/ S=C/ \CH let/Q Ha CHg 8. A material as defined in claim 1 wherein said compound is /CE1 /S EH2 \C S H o N/CHz-CH:
CHrCHz 9. A material as defined in claim 1 wherein said compound is 10. A material as defined in claim 1 wherein said com- References Cited FOREIGN PATENTS 660,222 2/1965 France.
I. TRAVIS BROWN, Primary Examiner. I. R. EVERETT, Assistant Examine'r.
US. Cl. X.R.
Claims (1)
1. A PHOTOGRAPHIC SILVER HALIDE SENSITIVE MATERIAL COMPRISING A SUPPORT AND A SILVER HALIDE EMULSION LAYER, SAID LAYER CONTAINING AT LEAST ONE COMPOUND SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS REPRESENTED BY THE GENERAL FORMULA:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6397364 | 1964-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3433640A true US3433640A (en) | 1969-03-18 |
Family
ID=13244722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US506842A Expired - Lifetime US3433640A (en) | 1964-11-13 | 1965-11-08 | Photographic silver halide light-sensitive material |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3433640A (en) |
| FR (1) | FR1509920A (en) |
| GB (1) | GB1086657A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2822320A1 (en) * | 1977-05-23 | 1978-12-07 | Fuji Photo Film Co Ltd | PHOTOGRAPHIC SILVER HALOGENIDE EMULSION |
| US4610954A (en) * | 1983-11-08 | 1986-09-09 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
| EP0239369A1 (en) * | 1986-03-24 | 1987-09-30 | Minnesota Mining And Manufacturing Company | Bis (thiazolinethiones) |
| US4946962A (en) * | 1986-03-24 | 1990-08-07 | Minnesota Mining And Manufacturing Company | Bis(thiazolinethiones) |
| US20040131982A1 (en) * | 2002-12-19 | 2004-07-08 | Agfa-Gevaert | Toning agents for use in substantially light-insensitive recording materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659801A (en) * | 1985-12-10 | 1987-04-21 | Minnesota Mining And Manufacturing Company | Thiazolinethione-containing polymer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR660222A (en) * | 1928-09-11 | 1929-07-09 | Improvements in vacuum cleaners for flue gas pipes and others |
-
1965
- 1965-11-04 GB GB46814/65A patent/GB1086657A/en not_active Expired
- 1965-11-08 US US506842A patent/US3433640A/en not_active Expired - Lifetime
- 1965-11-13 FR FR38299A patent/FR1509920A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR660222A (en) * | 1928-09-11 | 1929-07-09 | Improvements in vacuum cleaners for flue gas pipes and others |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE2822320A1 (en) * | 1977-05-23 | 1978-12-07 | Fuji Photo Film Co Ltd | PHOTOGRAPHIC SILVER HALOGENIDE EMULSION |
| US4610954A (en) * | 1983-11-08 | 1986-09-09 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive material |
| EP0239369A1 (en) * | 1986-03-24 | 1987-09-30 | Minnesota Mining And Manufacturing Company | Bis (thiazolinethiones) |
| AU586914B2 (en) * | 1986-03-24 | 1989-07-27 | Minnesota Mining And Manufacturing Company | Bis (thiazolinethiones) |
| US4946962A (en) * | 1986-03-24 | 1990-08-07 | Minnesota Mining And Manufacturing Company | Bis(thiazolinethiones) |
| US20040131982A1 (en) * | 2002-12-19 | 2004-07-08 | Agfa-Gevaert | Toning agents for use in substantially light-insensitive recording materials |
| US7045487B2 (en) | 2002-12-19 | 2006-05-16 | Agfa Gevaert | Toning agents for use in substantially light-insensitive recording materials |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1509920A (en) | 1968-01-19 |
| GB1086657A (en) | 1967-10-11 |
| DE1547821A1 (en) | 1969-12-11 |
| DE1547821B2 (en) | 1976-02-12 |
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