US3888677A - Silver halide photographic material containing antifog agent with protected mercapto group - Google Patents
Silver halide photographic material containing antifog agent with protected mercapto group Download PDFInfo
- Publication number
- US3888677A US3888677A US405801A US40580173A US3888677A US 3888677 A US3888677 A US 3888677A US 405801 A US405801 A US 405801A US 40580173 A US40580173 A US 40580173A US 3888677 A US3888677 A US 3888677A
- Authority
- US
- United States
- Prior art keywords
- photographic material
- radical
- material according
- silver halide
- antifog agent
- 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
- -1 Silver halide Chemical class 0.000 title claims abstract description 42
- 239000000463 material Substances 0.000 title claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 19
- 229910052709 silver Inorganic materials 0.000 title abstract description 19
- 239000004332 silver Substances 0.000 title abstract description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 title description 4
- 239000000839 emulsion Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 claims description 3
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims 2
- 229940125898 compound 5 Drugs 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 description 15
- 230000035945 sensitivity Effects 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 5
- 150000007970 thio esters Chemical class 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 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
- RCJRILMVFLGCJY-UHFFFAOYSA-N 4-phenyl-1,3-dioxane Chemical compound O1COCCC1C1=CC=CC=C1 RCJRILMVFLGCJY-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
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002731 mercury compounds Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 102220022547 rs386833639 Human genes 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- ABSTRACT The invention relates to silver halide photographic material containing an antifog agent having the formula wherein A is a nitrogen-containing heterocyclic radical or a 4-acetaminophenyl radical,
- R is H, alkyl of l to 4 carbon atoms, aryl or CO CH-S -A and n is 2 to 4.
- the stabilizers from the class of triazaindolizines which are outstandingly suitable for the prevention of storage fog, do not provide suitable protection against overdevelopment fog, because their protective action abates and practically disappears through diffusion displacement and other mechanisms toward the end of the development exactly when they are most needed.
- Other stabilizers of known effectiveness such as mercury compounds or heterocyclic mercapto compounds are indeed capable of reducing the development fog in the normal and also in the overdevelopment region, but have the big disadvantage that when used in sufficient quantities they reduce considerably the sensitivity of the photographic emulsions.
- a fundamental disadvantage of the direct addition of the heterocyclic mercapto compounds, which in themselves are particularly active against overdevelopment fog, to silver halide emulsions consists in that they are completely active from the time of their addition, that is, also during the casting process, during the total time of storage of the unprocessed film material and finally already in the initial stage of the photographic development. Therefore, one is forced to accept desensitization effects even before processing, and incomplete utilization of the sensitivity of the material during the development itself.
- Substituents of the thioester type for example carboxylic acid or sulfonic acid groups, or groupings of carbonic acid derivatives, for example carbalkoxyl groups, are known from many Patents: for example, from German Pat. No. 1,597,503, U.S. Pat. No. 3,260,597 and German Offenlegungsschrift No. 2,061,972. They all have the disadvantage that they do indeed cleave more or less rapidly in the alkaline medium of the developer, but hydrolytic cleavage takes place, even though slowly, already in neutral or weakly acid pH regions.
- substituents of the thioether type for example, those of U.S. Pat. Nos. 2,981,624 and 3,260,597, German Pat. No. 1,173,796 and German Offenlegungsschrift No. 1,908,217, are indeed stable in neutral or weakly acid media, but do not react during the development process, or react much too slowly or only at higher concentrations and, therefore, cannot prevent overdevelopment fog, at least not in the desired degree.
- an object of the present invention consists in providing antifog agents with inactivated mercapto groups which are completely stable in the neutral or weakly acid pH region of the emulsion but, on the other hand, in the alkaline pH region liberate the active stabilizer to the desired extent during development.
- Suitable compounds of this type are listed in Table 1 under the numbers l-9, of which the compounds 2, 5, 6 and 9 are preferred in the present invention.
- heterocyclic radicals A contemplated are, for example, the thiodiazolyl, thiazolyl, oxazolyl, imidazolyl, benzimidazolyl, pyrimidinyl and triazolyl radicals.
- the heterocyclic radical A is the heterocyclic radical of a mercapto antifog agent and is usually substituted as illustrated in the compounds of Table 1. Compounds derivable from l-phenyl-5-mercaptotetrazole are particularly preferred. In such compounds, A is a lphenyltetrazolyl radical as shown in Compounds 1-4 and 8 of the compounds of the invention. It is preferred that the heterocyclic radical A have 5 or 6 atoms in the heterocyclic ring.
- the antifog agents are added to the light-sensitive emulsions or also to the light-insensitive auxiliary layers, such as interlayers, protective layers and the like.
- the addition takes place most favorably before casting the emulsion, but it is also possible to add the compounds at another point in the production of the emulsion.
- the compounds When used in the emulsion layer itself, the compounds preferably are added in quantities of 0.05 to mmol based on 1.0 mols of silver halide added, whereas in the auxiliary layers they display the best effect in quantities of 0.1 to 5 mmols.
- the optimum quantity naturally depends on the nature of the antifog agent and the emulsion used and can be determined easily from case to case.
- the compounds described can be dissolved in a suitable solvent and added to the emulsion in this form. If the solubility of the compounds in water-miscible organic solvents is too small, they can also be dissolved in a known manner in water-immiscible organic solvents and added in the form of a dispersion.
- suitable solvents are 4-phenyl-1,3-dioxane, tributyl phosphate, diethyl phthalate, ethyl acetate, phenyl glycol and the like.
- the new antifog agents can be used in the most varied kinds of reproduction materials, for example, in nonoptically sensitized materials, such as X-ray films, but just as well also in orthochromatically and panchromatically sensitized reproducing materials.
- the light-sensitive emulsions used may contain the customary additives, such as chemical sensitizers, hardeners, wetting agents, and the like.
- the new antifog agents can be used in mixtures with one another or in combination with other antifog agents.
- EXAMPLE 1 This example describes the preparation of Compound 6 of Table 1. 4-Mercaptoacetanilide (1.67g 0.01 mol) is heated to boiling under reflux for 3 hours with 1.25 g (0.01 mol) of N-ethylmaleimide in 50 ml of ethanol. Subsequently the mixture is evaporated to dryness in a vacuum and the residue is recrystallized from 1:1 ehtanol/benzene. Yield: Practically quantitative Mp 179 C.
- the emulsion is divided into five portions A, B, C, D and E.
- Portion A contains no additive and serves as a comparison sample.
- the quantities of additives, dissolved in acetone, presented in Table 3 were added to portions B, C, D and E per mol of silver bromide. Subsequently the portions A to D were halved (part I and part 11) and cast on a polyester film base immediately or after 1 hour/35 C.
- the light-sensitive material was evaluated in the customary manner.
- Hydroquinone 30.00g l-Phenyl-3-pyrazolidone 1.00g Na SO (anhydrous) 60.00g KOH 23.00g NaB0 -4H O 20.00g water to make up to 1 l.
- the products were then fixed in a customary fixing bath, subsequently Washed and dried.
- the value for the general sensitivity of the comparison emulsion is set equal to 100:
- EXAMPLE 5 A silver halide emulsion prepared according to the information of Example 4 is divided into seven parts A, B, C, D, E, F and G, in doing which part A serves as a comparison sample. To each of the remaining parts one of the additives in Table 4 in acetone solution was added and after a standing time of 1 hour at 35 C was cast on a polyester film base. The further processing followed that in Example 4.
- the silver halide consists of 98 weight percent of silver bromide and 2 weight percent of silver iodide.
- the emulsion produced in this way is divided into three parts A, B and C.
- Part A contains no additive and serves as a comparison sample.
- Parts B and C contain the quantities of additives given in Table 5 per mol of silver bromide. After a standing time of 1 hour at 35 C the emulsions are cast on a polyester film base and processed further as in Example 4.
- a silver halide emulsion prepared like that in Example 6 is divided into four parts A, B, C and D, whereby part A serves as a comparison sample.
- To each of the remaining parts B, C and D is added per mol of silver bromide one of the additives presented in Table 6 in acetone solution and, after a standing time of one hour at A silver halide emulsion prepared according to the information in Example 4 is divided into three parts A, B and C.
- Part A contains no additive and serves as a comparison sample.
- Parts B and C contain the quantities of additives per mol given in Table 7. After a standing time of 1 hour at 35 C, the emulsions are cast on a polyester film base and processed further as in Example 4.
- the new stabilizers are characterized chiefly in that, at pH values of l and above, they are very easily cleavable, whereas they are absolutely stable at the same time in the pH region between 3 and 7.
- these compounds even when they are in contact with the light-sensitive emulsion for a long time before the casting, which is always the case under production conditions, are stable and display no tendency toward hydrolysis in this pH region, so that even with very long standing time, there is no desensitization.
- Photographic material comprising a film support and at least one light-sensitive silver halide emulsion layer containing an antifog agent or being in contact with an auxiliary layer containing an antifog agent, said antifog agent being present in an antifogging amount and having the formula:
- A represents a 4-acetaminophenyl radical. 5. Photographic material according to claim wherein A represents a benzoxazolyl radical.
- Photographic material according to claim wherein A is selected from l-phenyltetrazolyl, benzothiazolyl, 4-acetaminophenyl, and benzoxazolyl radicals.
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)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722250136 DE2250136C3 (de) | 1972-10-13 | Photographisches Aufzeichnungsmaterial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3888677A true US3888677A (en) | 1975-06-10 |
Family
ID=5858883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US405801A Expired - Lifetime US3888677A (en) | 1972-10-13 | 1973-10-12 | Silver halide photographic material containing antifog agent with protected mercapto group |
Country Status (4)
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4307175A (en) * | 1979-09-28 | 1981-12-22 | Agfa-Gevaert, N.V. | Photographic silver halide emulsion material containing an antifoggant precursor |
| US4335200A (en) * | 1980-10-30 | 1982-06-15 | Mitsubishi Paper Mills, Ltd. | Silver halide photographic materials |
| EP0055858A2 (en) | 1981-01-05 | 1982-07-14 | Polaroid Corporation | Photographic products, diffusion transfer photographic process, and compounds used therefor |
| US4420554A (en) * | 1981-02-17 | 1983-12-13 | Mitsubishi Paper Mills, Ltd. | Silver halide photosensitive materials |
| US4618563A (en) * | 1983-08-15 | 1986-10-21 | Fuji Photo Film Co., Ltd. | Photographic light-sensitive material |
| EP2107122A1 (en) | 2008-03-31 | 2009-10-07 | FUJIFILM Corporation | Protease detection material, set of protease detection materials, and method for measuring protease |
| WO2014127297A1 (en) | 2013-02-15 | 2014-08-21 | Cambrios Technologies Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
| US10720257B2 (en) | 2013-02-15 | 2020-07-21 | Cambrios Film Solutions Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
| US10971277B2 (en) | 2013-02-15 | 2021-04-06 | Cambrios Film Solutions Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2697100A (en) * | 1952-05-31 | 1954-12-14 | Eastman Kodak Co | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
| US2939789A (en) * | 1958-06-06 | 1960-06-07 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
| US2948612A (en) * | 1959-03-03 | 1960-08-09 | Gen Aniline & Film Corp | Photographic materials and method of producing the same |
| US2981624A (en) * | 1957-06-05 | 1961-04-25 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
-
1973
- 1973-10-12 BE BE136655A patent/BE806037A/xx unknown
- 1973-10-12 US US405801A patent/US3888677A/en not_active Expired - Lifetime
- 1973-10-12 GB GB4785373A patent/GB1402819A/en not_active Expired
- 1973-10-13 JP JP11437573A patent/JPS5517369B2/ja not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2697100A (en) * | 1952-05-31 | 1954-12-14 | Eastman Kodak Co | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
| US2981624A (en) * | 1957-06-05 | 1961-04-25 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsion |
| US2939789A (en) * | 1958-06-06 | 1960-06-07 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
| US2948612A (en) * | 1959-03-03 | 1960-08-09 | Gen Aniline & Film Corp | Photographic materials and method of producing the same |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4307175A (en) * | 1979-09-28 | 1981-12-22 | Agfa-Gevaert, N.V. | Photographic silver halide emulsion material containing an antifoggant precursor |
| US4335200A (en) * | 1980-10-30 | 1982-06-15 | Mitsubishi Paper Mills, Ltd. | Silver halide photographic materials |
| EP0055858A2 (en) | 1981-01-05 | 1982-07-14 | Polaroid Corporation | Photographic products, diffusion transfer photographic process, and compounds used therefor |
| US4420554A (en) * | 1981-02-17 | 1983-12-13 | Mitsubishi Paper Mills, Ltd. | Silver halide photosensitive materials |
| US4618563A (en) * | 1983-08-15 | 1986-10-21 | Fuji Photo Film Co., Ltd. | Photographic light-sensitive material |
| EP2107122A1 (en) | 2008-03-31 | 2009-10-07 | FUJIFILM Corporation | Protease detection material, set of protease detection materials, and method for measuring protease |
| WO2014127297A1 (en) | 2013-02-15 | 2014-08-21 | Cambrios Technologies Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
| EP3598185A2 (en) | 2013-02-15 | 2020-01-22 | Cambrios Film Solutions Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
| US10720257B2 (en) | 2013-02-15 | 2020-07-21 | Cambrios Film Solutions Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
| US10971277B2 (en) | 2013-02-15 | 2021-04-06 | Cambrios Film Solutions Corporation | Methods to incorporate silver nanowire-based transparent conductors in electronic devices |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1402819A (en) | 1975-08-13 |
| DE2250136B2 (de) | 1975-10-09 |
| JPS4974930A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-19 |
| JPS5517369B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-05-10 |
| BE806037A (fr) | 1974-04-12 |
| DE2250136A1 (de) | 1974-05-02 |
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