US3042521A - Antifoggants and stabilizers for photographic silver halide emulsion - Google Patents
Antifoggants and stabilizers for photographic silver halide emulsion Download PDFInfo
- Publication number
- US3042521A US3042521A US705151A US70515157A US3042521A US 3042521 A US3042521 A US 3042521A US 705151 A US705151 A US 705151A US 70515157 A US70515157 A US 70515157A US 3042521 A US3042521 A US 3042521A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- emulsion
- acid
- antifoggants
- stabilizers
- 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 description 56
- 239000000839 emulsion Substances 0.000 title claims description 36
- 229910052709 silver Inorganic materials 0.000 title claims description 20
- 239000004332 silver Substances 0.000 title claims description 20
- 239000003381 stabilizer Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 229960004635 mesna Drugs 0.000 description 14
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 11
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- CSJDJKUYRKSIDY-UHFFFAOYSA-N 1-sulfanylpropane-1-sulfonic acid Chemical compound CCC(S)S(O)(=O)=O CSJDJKUYRKSIDY-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000005070 ripening Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000011161 development Methods 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
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000001235 sensitizing effect Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- HNFOAHXBHLWKNF-UHFFFAOYSA-M sodium;2-bromoethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)CCBr HNFOAHXBHLWKNF-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000005425 toluyl group Chemical group 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/46—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
Definitions
- the present invention relates to the use of anti-fogging and stabilizing agents for photographic silver halide emul' sions and, more particularly, to the use of sulfoalkyl-Z- thiazolyland oxazolylthio ethers, their salts and esters for such purpose.
- Benzthiazole and its derivatives such as Z-mercaptobenzthiazole, have been recommended as being etfective in preventing any increase in fog through stabilizing or controlling the keeping qualities of light-sensitive silver halide emulsions. Although these compounds have the ability to reduce fog tendencies and to improve stability, they are deficient in that they lower the sensitivity of the emulsions and in many cases reduce optical and dye sensitivity.
- sulfoalkyl-Z-thiazolylthio ethers and the corresponding oxazolylthio ethers, their salts and esters are not only excellent stabilizers or antifogging agents for light-sensitive silver halide emulsions but, in addition, they have the faculty of performing this function without lowering the sensitivity of the emulsion with which they are associated or without reducing the sensitivity of the emulsion to light of longer wave length attributable to the presence of sensitizing dyes.
- antifoggants the use of which is contemplated herein, may be represented by the following formula:
- R is hydrogen, an aliphatic radical such as 'alkyl, i.e., methyl, ethyl, propyl, butyl, amyl and the like; hydroxyalkyl, i.e., hydroxymethyl, hydroxyethyl and the like; carboxyalkyl, i.e., carboxymethyl, carboxyethyl and the like; aryl such as phenyl, toluyl, naphthyl, carboxyphenyl, sulfophenyl and the like; aralkyl such as benzyl or a salt-forming group such as sodium, potassium, ammonium, silver or the like; R is hydrogen, alkyl as above, aryl as above or carboxyalkyl as above or both Rs together form a fused-on aromatic ring such as benzo or naphtho, said benzo or naphtho ring if desired bearing a substituent such as halogen, i.e., chloro,
- the product After allowing the mixture to stand overnight, the product is filtered and dried. It may be recrystallized from ethanol and dried at room temperature.
- the product was obtained in this procedure in the form of its alkali metal salt. If the free acid be desired, it is obtained by passing a solution of the alkali metal salt through an anion exchange resin such as those described in US. Patent 2,732,352 or 2,591,573.
- esters may be produced in the conventional manner by refluxing the free acid with the desired alcohol or phenol in the presence of hydrochloric acid.
- the concentration used depends very much on the type of emulsion employed and it is advisable to determine the optimum concentration from case to case.
- the antifoggant in layers adjacent to the emulsion, that is, in a separate undercoating layer or in the anti-abrasion gelatin surface.
- the desired result may be obtained by adding the antifoggant to one or several of the processing baths, i.e., developer or fixer for the involved emulsion.
- antifoggants and stabilizers may be employed in connection with any type of photographic emulsion, e.g., non-sensitized, orthochromatic, panchromatic, X-ray emulsions, paper emulsions, color emulsions or the like. They may be used in combination with other known antifoggants and stabilizers, reductionand metaland noble metal sensitizers or in combination with hydroxypolyethenoxy derivatives, i.e., those obtained by reacting ethyleneoxide with an alcohol, phenol, amine or the like (see US. Patent 1,970,578).
- Example I A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide was prepared in a conventional manner and brought up to its maximum light sensitivity. It was then readied for coating, finals were added such as sensitizing dyes, and hardening agents. A 1% solution of the sodium salt of fi-(Z-benzthiazolyhmercaptoethanesulfonic acid in water was prepared and added to the emulsion as an antifoggant and stabilizer. The emulsion samples contained about .4 mol of silver halide. The so prepared emulsion samples were coated on a suitable cellulose ester base and dried. Samples of these coatings were then exposed in a type IIB sensitometer and developed in a developer of the following composition:
- Example 11 4 that the sodium salt of p-(2-benzthiazolyl)-mercaptoethanesulfonic acid was replaced by an equivalent quantity of fl(2-benzoxazolyl)mercaptoethanesulfonic acid sodium salt.
- the benzoxazolyl derivates was prepared in the same fashion as the benzthiazolyl derivate excepting that the Z-mercaptobenzthiazole was replaced by an equivalent quantity of Z-mercaptobenzoxazole.
- Example III The procedure was the same as in Example I excepting that there was employed as the antifoggant -(2-benzthiazolyl)-mercaptopropanesulfonic acid. The results were similar to those of Example I.
- the antifoggant of this example was prepared in the same manner as that of Example I excepting that the 2-bromoethanesulfonic acid sodium salt was replaced by an equivalent quantity of 'y-bromopropanesulfonic acid sodium salt.
- Example IV Exposed samples of a photographic film were developed for twelve minutes at 65 F. in a standard metolhydroquinone developer. Two tests were made, one with the normal developing solution and one with a developer containing mgs. of the sodium salt of fl-(2-benzthiazolyl)mercaptoethanesulfonic acid 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 V The procedure was the same as in Example IV excepting that the )3-(2-benzthiazolyl)mercaptoethanesulfonic acid was replaced by an equivalent quantity of p-(2-benzoxazolyl)mercaptoethanesulfonic acid. The results were substantially the same as those obtained in Example IV.
- a light-sensitive photographic material comprising a base and a light-sensitive silver halide emulsion thereon, said light-sensitive material containing as an antifoggant a compound selected from the class consisting of those of the following formulae:
- R is selected from the class consisting of hydrogen, alkyl, hydroxylalkyl, carboxyalkyl, aryl, aralkyl and a cation; R is selected from the class consisting of hydrogen, alkyl, aryl and carboxyalkyl; X represents the atoms necessary to complete a nucleus selected from the class consisting of those of the benzene and naphthalene series; Y is selected from the class consisting of oxygen and sulfur and n is a whole number of from 2 to 3 2.
- said antifoggant is located in the silver halide emulsion.
- a light-sensitive photographic material comprising a base with a light-sensitive silver halide emulsion thereon, said emulsion containing as an antifoggant the compound B-(Z-benzthiazolyl)mercaptoethanesulfonic acid sodium salt of the formula:
- R is selected from the class consisting of hydrogen, an alkyl, hydroxyalkyl, carboxyalkyl, aryl, aralkyl and a cation; R is selected from the class consisting of 1 References Cited in the file of this patent UNITED STATES PATENTS 2,186,849 Wilmanns et al. Jan. 9, 1940 2,490,745 Carroll et al. Dec. 6, 1949 2,697,100 Knott Dec, 14, 1954 2,819,965 Murray et al. Jan. 14, 1958 2,915,395 Popeck et al Dec. 1, 1958 FOREIGN PATENTS 973,727 France Sept. 20, 1950
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE572846D BE572846A (enrdf_load_stackoverflow) | 1957-12-26 | ||
| US705145A US2902367A (en) | 1957-12-26 | 1957-12-26 | Photographic developer antioxidant |
| US705151A US3042521A (en) | 1957-12-26 | 1957-12-26 | Antifoggants and stabilizers for photographic silver halide emulsion |
| DEG26026A DE1093205B (de) | 1957-12-26 | 1958-12-23 | Antischleier- und Stabilisierungsmittel fuer lichtempfindliches photographisches Material |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US705145A US2902367A (en) | 1957-12-26 | 1957-12-26 | Photographic developer antioxidant |
| US705151A US3042521A (en) | 1957-12-26 | 1957-12-26 | Antifoggants and stabilizers for photographic silver halide emulsion |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3042521A true US3042521A (en) | 1962-07-03 |
Family
ID=27107440
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US705151A Expired - Lifetime US3042521A (en) | 1957-12-26 | 1957-12-26 | Antifoggants and stabilizers for photographic silver halide emulsion |
| US705145A Expired - Lifetime US2902367A (en) | 1957-12-26 | 1957-12-26 | Photographic developer antioxidant |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US705145A Expired - Lifetime US2902367A (en) | 1957-12-26 | 1957-12-26 | Photographic developer antioxidant |
Country Status (3)
| Country | Link |
|---|---|
| US (2) | US3042521A (enrdf_load_stackoverflow) |
| BE (1) | BE572846A (enrdf_load_stackoverflow) |
| DE (1) | DE1093205B (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189448A (en) * | 1962-08-22 | 1965-06-15 | Eastman Kodak Co | Developing compositions used in photographic transfer processes |
| US3206308A (en) * | 1959-12-28 | 1965-09-14 | Eastman Kodak Co | Photographic stratum transfer process and developing compositions therefor |
| US3250617A (en) * | 1962-03-29 | 1966-05-10 | Eastman Kodak Co | Photographic elements protected against ultraviolet radiation |
| US3732103A (en) * | 1971-05-03 | 1973-05-08 | Eastman Kodak Co | Silver halide emulsions containing alkyl selenols and thiols as antifoggants |
| US3808005A (en) * | 1968-02-22 | 1974-04-30 | Agfa Gevaert Nv | Silver halide emulsion stabilized with a bidentate heterocyclic compound containing a sulpho or a carboxyl group |
| USRE28668E (en) * | 1971-05-03 | 1975-12-30 | Silver halide emulsions containing alkyl selenols and thiols as antifoggants | |
| US4144068A (en) * | 1977-01-28 | 1979-03-13 | Fuji Photo Film Co., Ltd. | Method for color photographic processing |
| US5415992A (en) * | 1993-11-30 | 1995-05-16 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing phosphine compounds |
| US5443947A (en) * | 1993-11-30 | 1995-08-22 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing thiosulfonate/sulfinate compounds |
| US5536633A (en) * | 1993-11-30 | 1996-07-16 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing sulfur donors and sulfinate compounds |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1209925A (fr) * | 1957-03-08 | 1960-03-04 | Kodak Pathe | Nouveau procédé de traitement pour la photographie en couleurs et révélateur pour sa mise en oeuvre |
| US3030209A (en) * | 1958-07-02 | 1962-04-17 | Eastman Kodak Co | High-contrast photographic silver chloride emulsions and method of processing |
| US3128180A (en) * | 1958-07-02 | 1964-04-07 | Eastman Kodak Co | Hardened high-contrast photographic silver chloride emulsions and method of processing |
| US3212895A (en) * | 1960-12-20 | 1965-10-19 | Eastman Kodak Co | Stability of rapid-processed photographic materials |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| US2490745A (en) * | 1948-01-13 | 1949-12-06 | Eastman Kodak Co | Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts |
| FR973727A (fr) * | 1947-10-16 | 1951-02-14 | Photo Produits Gevaert S A | Procédé pour la production d'émulsions photographiques à l'halogénure d'argent |
| US2697100A (en) * | 1952-05-31 | 1954-12-14 | Eastman Kodak Co | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
| US2819965A (en) * | 1956-02-23 | 1958-01-14 | Eastman Kodak Co | Carboxymethylmercapto compounds as stabilizers for photographic emulsions |
| US2915395A (en) * | 1957-02-15 | 1959-12-01 | Gen Aniline & Film Corp | Antifogging agents for light sensitive paper emulsions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2313523A (en) * | 1940-06-18 | 1943-03-09 | Eastman Kodak Co | Photographic material |
| GB643411A (en) * | 1947-03-06 | 1950-09-20 | Du Pont | Improvements in or relating to photographic developers |
-
0
- BE BE572846D patent/BE572846A/xx unknown
-
1957
- 1957-12-26 US US705151A patent/US3042521A/en not_active Expired - Lifetime
- 1957-12-26 US US705145A patent/US2902367A/en not_active Expired - Lifetime
-
1958
- 1958-12-23 DE DEG26026A patent/DE1093205B/de active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| FR973727A (fr) * | 1947-10-16 | 1951-02-14 | Photo Produits Gevaert S A | Procédé pour la production d'émulsions photographiques à l'halogénure d'argent |
| US2490745A (en) * | 1948-01-13 | 1949-12-06 | Eastman Kodak Co | Cellulose carboxylic ester silver halide emulsions sensitized with benzothiazole and benzoselenazole quaternary salts |
| US2697100A (en) * | 1952-05-31 | 1954-12-14 | Eastman Kodak Co | Alpha-acylthio-n(2-benzothiazolyl) succinimides |
| US2819965A (en) * | 1956-02-23 | 1958-01-14 | Eastman Kodak Co | Carboxymethylmercapto compounds as stabilizers for photographic emulsions |
| US2915395A (en) * | 1957-02-15 | 1959-12-01 | Gen Aniline & Film Corp | Antifogging agents for light sensitive paper emulsions |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206308A (en) * | 1959-12-28 | 1965-09-14 | Eastman Kodak Co | Photographic stratum transfer process and developing compositions therefor |
| US3250617A (en) * | 1962-03-29 | 1966-05-10 | Eastman Kodak Co | Photographic elements protected against ultraviolet radiation |
| US3189448A (en) * | 1962-08-22 | 1965-06-15 | Eastman Kodak Co | Developing compositions used in photographic transfer processes |
| US3808005A (en) * | 1968-02-22 | 1974-04-30 | Agfa Gevaert Nv | Silver halide emulsion stabilized with a bidentate heterocyclic compound containing a sulpho or a carboxyl group |
| US3732103A (en) * | 1971-05-03 | 1973-05-08 | Eastman Kodak Co | Silver halide emulsions containing alkyl selenols and thiols as antifoggants |
| USRE28668E (en) * | 1971-05-03 | 1975-12-30 | Silver halide emulsions containing alkyl selenols and thiols as antifoggants | |
| US4144068A (en) * | 1977-01-28 | 1979-03-13 | Fuji Photo Film Co., Ltd. | Method for color photographic processing |
| US5415992A (en) * | 1993-11-30 | 1995-05-16 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing phosphine compounds |
| US5443947A (en) * | 1993-11-30 | 1995-08-22 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing thiosulfonate/sulfinate compounds |
| US5536633A (en) * | 1993-11-30 | 1996-07-16 | Eastman Kodak Company | Heat stabilized silver chloride photographic emulsions containing sulfur donors and sulfinate compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| US2902367A (en) | 1959-09-01 |
| DE1093205B (de) | 1960-11-17 |
| BE572846A (enrdf_load_stackoverflow) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3042521A (en) | Antifoggants and stabilizers for photographic silver halide emulsion | |
| US3137578A (en) | Photographic emulsions containing 2-heterocyclic benzimidazole antifoggants | |
| US3226232A (en) | Fog reduction in silver halide emulsions with a diphenyldisulfide dicarboxylic acid | |
| US3397986A (en) | Photographic emulsion stabilized with bis (p-acylamidophenyl) disulfides | |
| US2981624A (en) | Antifoggants and stabilizers for photographic silver halide emulsion | |
| US3499761A (en) | Silver halide emulsions containing alkyl esters of benzimidazole carbamic acid antifogging agents | |
| US3071465A (en) | Fog reduction in silver halide emulsions by 2h-tetrazolium halides | |
| US3447925A (en) | Anti-fogging and anti-plumming disulfide compound for use in silver halide photographs | |
| US2983610A (en) | Sensitization of photographic emulsions | |
| US3081170A (en) | Fog reduction in photographic silver halide emulsions | |
| US3692527A (en) | Silver halide emulsion containing a mercapto pyrimidine derivative antifoggant | |
| US3161520A (en) | Fog reduction in photographic silver halide emulsions | |
| US2897081A (en) | Antifogging agent and bactericide for photographic emulsions | |
| US2939789A (en) | Fog reduction in photographic silver halide emulsions | |
| US2952539A (en) | Photographic emulsions and developers stabilized with purine compounds | |
| US2964404A (en) | Hardening of gelating with aziridinylsulfonyl compounds | |
| US2887378A (en) | Photographic silver halide emulsions containing thiol compounds | |
| US2948615A (en) | Antifoggants and stabilizers for photographic silver halide emulsions | |
| US2728667A (en) | Molecular compounds of mercury salts with benzothiazoles as fog inhibitors in a silver halide emulsion | |
| US2743181A (en) | Stabilized photographic silver halide emulsions | |
| US2848329A (en) | Supersensitization with bis-heterocyclic bases | |
| US3554758A (en) | Photographic light-sensitive material | |
| US3226231A (en) | Fog reduction in silver halide emulsions with 3-mercaptobenzoic acid | |
| US3026201A (en) | Antifoggants and stabilizers for photographic silver halide emulsions | |
| US2860985A (en) | Stabilization of photographic silver halide emulsions and means of increasing contrast |