US2948612A - Photographic materials and method of producing the same - Google Patents
Photographic materials and method of producing the same Download PDFInfo
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- US2948612A US2948612A US796756A US79675659A US2948612A US 2948612 A US2948612 A US 2948612A US 796756 A US796756 A US 796756A US 79675659 A US79675659 A US 79675659A US 2948612 A US2948612 A US 2948612A
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- emulsion
- silver halide
- light
- compound
- same
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- 239000000463 material Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title description 9
- 239000000839 emulsion Substances 0.000 claims description 31
- -1 SILVER HALIDE Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229910052709 silver Inorganic materials 0.000 claims description 19
- 239000004332 silver Substances 0.000 claims description 19
- 230000000087 stabilizing effect Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000003381 stabilizer Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LAABTJXWUKMZIV-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 LAABTJXWUKMZIV-UHFFFAOYSA-N 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 230000005070 ripening Effects 0.000 description 3
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UXDLKPXOLABTJY-UHFFFAOYSA-N benzene-1,4-diol 2-(methylamino)phenol Chemical compound CNC1=C(C=CC=C1)O.C1(O)=CC=C(O)C=C1 UXDLKPXOLABTJY-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- 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
- the present invention relates to antifogging and stabilizing agents for photographic silver halide emulsions and, more particularly, to light-sensitive silver halide materials containing as a stabilizing and antifogging agent a tn'azine each carbon atom of which is substituted by a heterocyclic thioether group.
- lightsensitive emulsions such as gelatino silver halide emulr 2,948,612 Patented Aug. .9, 1960 amount ranging from 1 milligram to 2 5,milligrams per 0.6 mol of silver halide and when used as a coating final they are preferably added in an amount ranging from 10 milligrams to 300 milligrams per 0.6 mol of silver halide.
- the optimum amountto be added depends primarily on the type of emulsion and should be determined individually in each case.
- Fog is usually caused by 4 a prolonged ripening of the emulsions, by prolonged storage especially at elevated temperatures and humidity, and by prolonged development.
- all stabilizing and antifogging compounds heretofore used in this art have the disadvantage that upon addi-,
- an object of this invention to produce a light-sensitive emulsion which is fast, stable, has a reduced tendency to fog and has good contrast.
- a further object of this invention resides in a'light-' sensitive emulsion which contains a compound which stabilizes the emulsion against fogging and at the same time does not materially reduce the speed and/or contrast of the emulsion.
- a still further object of invention is to provide a light-sensitive emulsion containing a compound which stabilizes the emulsion against foggingand at the same time does not appreciably reduce the sensitivity to light of longer wave length efiectd by the presence of sensitizing dyes.
- i 'Ihestabilizers and antifoggants contemplated for use herein may be typified by the following structural formula:
- w hich R is thiazolyl, ,imidazolyl, oxazolyl, benzothja'zolyl, benzimidazolyl or benzoxazolyl.
- the antifogging agents of our invention may be added qthe. ennrlsion at any stage during its process of production.- Thus, they may be added as a ripening final or as a. coating final? When added as a ripening final,
- the stabilizers and antifoggants of our invention may also be used in combination with known antifoggants and stabilizers.
- the antifoggants of our invntion can also be used in combination with sensitizers such as sulfur, metal and reduction sensitizers as well as with accelerators such as the polyoxyethylenes (see U.S.P. 1,970,578) and their,
- novl antifoggants of our invention may be used with various types of photographic emulsions, such as;
- the antifoggants and stabilizers of the present invention are preparedby the dropwise addition to an organic solvent solution of cyanuric chloride of a Z-mercaptobenzothiazole, -benzimidazole,' -benzoxazole, -thiazole,
- the mixture is stirred at a temperature of from 5.0 C.
- the resulting solid may be.
- Example I A silver halide emulsion in gelatin containing 2% silver ventional rnanner and brought up to-its maxim-um light sensitivity. It was then readied for coating, finals were added such as sensitizing dyes and harden'ing agents. A 1% solution of 2,4,6-tni (benzothiazolyl-2-thio)-S-tri- -azine was prepared and added in varying amounts to samples of the emulsion as an antifoggant and stabilizer.”
- Each emulsion sample contained'about 0.6 mol of silver halide.
- the so-prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these film coatings were then-exposed in a Type 'IIB Sensitometer, and developed in a developerofthe following composition:
- Example 11 Exposed samples of a photographic film were developed for twelve minutes at 65 F. in a standard p-(N-methylamino)phenol hydroquinone developer. Two tests were made, one with the normal developing solution and one with a developer containing 100 mgs. of 2,4,6-tri (benzothiazolyl-2-thio)-S-t1iazine 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 .20.
- Example III The procedure is the same as in Example I excepting that the antifoggant and stabilizer is 2,4,6-tri (benzoxazolyl-Z-thio) -S-triazine. The results obtained with this compound are similar to those of Example I.
- This compound is prepared by the same method as that used in Example I excepting that the 2-mercaptobenzothiazole is replaced by .05 mol of Z-mercaptobenzoxazole.
- Example IV The procedure is the same as in Example II excepting that the antifoggant and stabilizer employed is 2,4,6-tri (imidazolyl-Z-thio) -S-triazine or 2,4,6-tri (thiazolyl-Z- thio)-S-tn'azine.
- a light-sensitive material comprising a base and a light-sensitive silver halide emulsion thereon, said material containing an antifoggant and stabilizing compound having the following chemical formula:
- R is selected from the group consisting of thiazolyl, imidazolyl, oxazolyl, benzothiazolyl, benzimidazolyl and benzoxazolyl.
- a light-sensitive photographic element as recited in claim 1 wherein the antifoggant and stabilizing compound is 2,4,6-tri (benzothiazolyl-Z-thio)-S-triazine.
- step 7 which comprises developing said emulsion with a p-(N-methylamino)phenol-hydroquinone developing solution in the presence of an antifogging and stabilizing compound having the following chemical formula:
- R is selected from the group consisting ofthiazolyl, imidazolyl, oxazolyl, benzothiazolyl, benzoimidazolyl and benzoxazolyl.
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)
Description
United States Patent PHOTOGRAPHIC MATERIALS AND METHOD or PRODUCING THE SAME Millet R. De Angelus and Fritz Dersch, Binghamton,
N.Y., assiguors to General Aniline & Film Corporation, New York, N.Y., a corporation of Delaware No Drawing. V Filed Mar. 3, 1959, Ser. No. 796,756
" '11 Claims. (Cl. 9 6-6 6 The present invention relates to antifogging and stabilizing agents for photographic silver halide emulsions and, more particularly, to light-sensitive silver halide materials containing as a stabilizing and antifogging agent a tn'azine each carbon atom of which is substituted by a heterocyclic thioether group. a
It is well known in the photographic art that lightsensitive emulsions, such as gelatino silver halide emulr 2,948,612 Patented Aug. .9, 1960 amount ranging from 1 milligram to 2 5,milligrams per 0.6 mol of silver halide and when used as a coating final they are preferably added in an amount ranging from 10 milligrams to 300 milligrams per 0.6 mol of silver halide. The optimum amountto be added depends primarily on the type of emulsion and should be determined individually in each case.
sions, have a tendency to fog. Fog is usually caused by 4 a prolonged ripening of the emulsions, by prolonged storage especially at elevated temperatures and humidity, and by prolonged development. To overcome this undesirable-property, it has been the practice in this art to add certain chemical compounds to the emulsions to increase theirstability and to reduce their tendency to fog. However, all stabilizing and antifogging compounds heretofore used in this art have the disadvantage that upon addi-,
tion to the emulsion thy cause a loss of speed and/or contrast of the emulsion.
It is, accordingly, an object of this invention to produce a light-sensitive emulsion which is fast, stable, has a reduced tendency to fog and has good contrast.
A further object of this invention resides in a'light-' sensitive emulsion which contains a compound which stabilizes the emulsion against fogging and at the same time does not materially reduce the speed and/or contrast of the emulsion. I
A still further object of invention is to provide a light-sensitive emulsion containing a compound which stabilizes the emulsion against foggingand at the same time does not appreciably reduce the sensitivity to light of longer wave length efiectd by the presence of sensitizing dyes.
Other objects andvadvantages of this invention will ap' pear to those skilled in the art from the detailed description,t-l1ereof given below.
i 'Ihestabilizers and antifoggants contemplated for use herein may be typified by the following structural formula:
-3. in w hich R, is thiazolyl, ,imidazolyl, oxazolyl, benzothja'zolyl, benzimidazolyl or benzoxazolyl.
The antifogging agents of our invention may be added qthe. ennrlsion at any stage during its process of production.- Thus, they may be added as a ripening final or as a. coating final? When added as a ripening final,
The stabilizers and antifoggants of our invention may also be used in combination with known antifoggants and stabilizers. The antifoggants of our invntion can also be used in combination with sensitizers such as sulfur, metal and reduction sensitizers as well as with accelerators such as the polyoxyethylenes (see U.S.P. 1,970,578) and their,
derivatives and polyvinyl-pyrrolidone.
The novl antifoggants of our invention may be used with various types of photographic emulsions, such as;
non-sensitized, orthochromatic, panchromatic and X-ray emulsions, paper emulsions and color emulsions.
The antifoggants and stabilizers of the present invention'are preparedby the dropwise addition to an organic solvent solution of cyanuric chloride of a Z-mercaptobenzothiazole, -benzimidazole,' -benzoxazole, -thiazole,
-imidazole or -oxazole while the latter is dissolved in an aqueous low boiling organicsolvent such as acetone, butyl acetate or thelike in the presence of an acid binding agent 9 such as potassium hydroxide, sodium hydroxide, sodium The following examples illustrate a method of preparg iodide and'98% silver bromide was prepared in a concarbonate or the like. After commingling the reactants,
the mixture is stirred at a temperature of from 5.0 C.
and. then chilled and filtered. The resulting solid may be.
purified by washing with. acetone and recrystallized from benzene. V
ing'one of the compounds falling under the general formula given above and the manner of using the compound in conjunction with light-sensitive photographic silver halide emulsion. his to be understood, however, that these examples are given by way of illustration only and not by way of limitation.
Example I A silver halide emulsion in gelatin containing 2% silver ventional rnanner and brought up to-its maxim-um light sensitivity. It was then readied for coating, finals were added such as sensitizing dyes and harden'ing agents. A 1% solution of 2,4,6-tni (benzothiazolyl-2-thio)-S-tri- -azine was prepared and added in varying amounts to samples of the emulsion as an antifoggant and stabilizer."
Each emulsion sample contained'about 0.6 mol of silver halide. The so-prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these film coatings were then-exposed in a Type 'IIB Sensitometer, and developed in a developerofthe following composition:
Grams I The results obtained were as follows:
Oven Fog .at; 6 Development Relative The compound 2,4,6-tri (benzothiazolyl-Z-thio) -S- triazme used above has the following chemical structure:
The method used by us in preparing this compound is as follows:
To a stirred solution containing 8.4 grams of (.05 mol) Z-mercaptobenzothiazole, 150 ml. of acetone, 8 ml. of H 0, and 3.3 grams of potassium hydroxide (.05 mol) was added dropwise a solution containing 3.1 gram (.017 mol) of cyanuric chloride in 100 ml. of acetone. The addition was carried out at room temperature. The stirred reaction mixture was heated to 60 C. for hours, and then chilled and filtered. The solid was washed with 20 ml. of acetone, then with water until free of the inorganic salts. After crystallization from benzene, the pale yellow product melted at 210-211" C. (uncorrected). Yield-5 grams. Calcd. for C H N S N: calcd., 14.58%; found, 14.53% S: calcd., 33.33%; found, 33.14%
Example 11 Exposed samples of a photographic film were developed for twelve minutes at 65 F. in a standard p-(N-methylamino)phenol hydroquinone developer. Two tests were made, one with the normal developing solution and one with a developer containing 100 mgs. of 2,4,6-tri (benzothiazolyl-2-thio)-S-t1iazine 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 .20.
Example III The procedure is the same as in Example I excepting that the antifoggant and stabilizer is 2,4,6-tri (benzoxazolyl-Z-thio) -S-triazine. The results obtained with this compound are similar to those of Example I.
This compound is prepared by the same method as that used in Example I excepting that the 2-mercaptobenzothiazole is replaced by .05 mol of Z-mercaptobenzoxazole.
Example IV The procedure is the same as in Example II excepting that the antifoggant and stabilizer employed is 2,4,6-tri (imidazolyl-Z-thio) -S-triazine or 2,4,6-tri (thiazolyl-Z- thio)-S-tn'azine.
These compounds are prepared in the same manner as the compound of Example I, excepting that 2-mercaptoirnidazole or 2-mercapto-thiazole is used in lieu of the 2- mercapto-benzothiazole.
Modifications of the invention will occur to persons skilled in the art. We, therefore, do not intend to be limited in the patent granted except as necessitated by the appended claims.
4 We claim: 1. A light-sensitive material comprising a base and a light-sensitive silver halide emulsion thereon, said material containing an antifoggant and stabilizing compound having the following chemical formula:
wherein R is selected from the group consisting of thiazolyl, imidazolyl, oxazolyl, benzothiazolyl, benzimidazolyl and benzoxazolyl.
2. A light-sensitive silver halide emulsion containing 2,4,6tri (benzothiazolyl-2thio)-S-triazine as an antifogw gant and stabilizer.
3. A light-sensitive silver halide material as recited in claim 1 wherein the antifoggant and stabilizing compound is present in the emulsion and in the ratio of 1 to 300 milligrams per 0.6 mol of silver halide.
' 4. A light-sensitive silver halide emulsion as recited in claim 2 wherein the antifoggant and stabilizing compound is present in the emulsion in the ratio of 1 to 25 milligrams per 0.6 mol of silver halide.
5. A light-sensitive silver halide material as recited in claim 1 wherein the antifoggant and stabilizing compound is present in the emulsion and in the ratio of 10 to 300 milligrams per 0.6 mol of silver halide.
6. A light-sensitive photographic element as recited in claim 1 wherein the antifoggant and stabilizing compound is 2,4,6-tri (benzothiazolyl-Z-thio)-S-triazine.
7. In a process of developing an exposed silver halide emulsion, the step which comprises developing said emulsion with a p-(N-methylamino)phenol-hydroquinone developing solution in the presence of an antifogging and stabilizing compound having the following chemical formula:
ing solution containing a compound'having the following wherein R is selected from the group consisting ofthiazolyl, imidazolyl, oxazolyl, benzothiazolyl, benzoimidazolyl and benzoxazolyl.
10. A p (N-methylamino)phenol-hydroquinone de veloping solution containing 2,4,6-tri (benzothiazolykZ- thio) -S-triazine.
11. A p-(N-methylamino) phenol-hydroquinone developing solution containing milligrams of 2 ;46 tfi' (benzothiazolyl-Z-thio) S-triazine per liter of solution.
References Cited in the file of this patent UNITED STATES PATENTS 2,476,536 Dersch Ju y 1 .19
Claims (1)
1. A LIGHT-SENSTITIVE MATERIAL COMPRISING A BASE AND A LIGHT-SENSTITIVE SILVER HALIDE EMULSION THEREON, SAID MATERIAL CONTAINING ANTIFOGGANT AND STABILIZING COMPOUND HAVING THE FOLLOWING CHEMICAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US796756A US2948612A (en) | 1959-03-03 | 1959-03-03 | Photographic materials and method of producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US796756A US2948612A (en) | 1959-03-03 | 1959-03-03 | Photographic materials and method of producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2948612A true US2948612A (en) | 1960-08-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US796756A Expired - Lifetime US2948612A (en) | 1959-03-03 | 1959-03-03 | Photographic materials and method of producing the same |
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| US (1) | US2948612A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137578A (en) * | 1962-02-07 | 1964-06-16 | Eastman Kodak Co | Photographic emulsions containing 2-heterocyclic benzimidazole antifoggants |
| US3888677A (en) * | 1972-10-13 | 1975-06-10 | Du Pont | Silver halide photographic material containing antifog agent with protected mercapto group |
| FR2384282A1 (en) * | 1977-03-17 | 1978-10-13 | Wolfen Filmfab Veb | Stabilised photographic silver halide material - contg. azole thioether cpd. as antifoggant, avoiding desensitisation |
| US4710451A (en) * | 1986-03-24 | 1987-12-01 | Agfa-Gevaert N.V. | High contrast development of silver halide emulsion material |
| DE4023143A1 (en) * | 1989-07-21 | 1991-01-31 | Mitsubishi Paper Mills Ltd | Photographic developer stabilised with S-triazine mercapto cpd. - to prevent silver sludge without desensitisation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476536A (en) * | 1947-11-18 | 1949-07-19 | Gen Aniline & Film Corp | 1, 3, 5-triazines as stabilizing agents for silver-halide emulsions |
-
1959
- 1959-03-03 US US796756A patent/US2948612A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476536A (en) * | 1947-11-18 | 1949-07-19 | Gen Aniline & Film Corp | 1, 3, 5-triazines as stabilizing agents for silver-halide emulsions |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137578A (en) * | 1962-02-07 | 1964-06-16 | Eastman Kodak Co | Photographic emulsions containing 2-heterocyclic benzimidazole antifoggants |
| US3888677A (en) * | 1972-10-13 | 1975-06-10 | Du Pont | Silver halide photographic material containing antifog agent with protected mercapto group |
| FR2384282A1 (en) * | 1977-03-17 | 1978-10-13 | Wolfen Filmfab Veb | Stabilised photographic silver halide material - contg. azole thioether cpd. as antifoggant, avoiding desensitisation |
| US4710451A (en) * | 1986-03-24 | 1987-12-01 | Agfa-Gevaert N.V. | High contrast development of silver halide emulsion material |
| DE4023143A1 (en) * | 1989-07-21 | 1991-01-31 | Mitsubishi Paper Mills Ltd | Photographic developer stabilised with S-triazine mercapto cpd. - to prevent silver sludge without desensitisation |
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