US3244521A - Silver halide emulsions containing antifogging agents - Google Patents
Silver halide emulsions containing antifogging agents Download PDFInfo
- Publication number
- US3244521A US3244521A US149520A US14952061A US3244521A US 3244521 A US3244521 A US 3244521A US 149520 A US149520 A US 149520A US 14952061 A US14952061 A US 14952061A US 3244521 A US3244521 A US 3244521A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- light
- emulsion
- halide emulsions
- antifogging agents
- 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
- 239000000839 emulsion Substances 0.000 title description 32
- -1 Silver halide Chemical class 0.000 title description 28
- 229910052709 silver Inorganic materials 0.000 title description 25
- 239000004332 silver Substances 0.000 title description 25
- 239000003795 chemical substances by application Substances 0.000 title description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- UKMWOQXXGRBQLC-UHFFFAOYSA-N 6-methyl-1,2-dihydropyrazolo[3,4-d]pyrimidine-4-thione Chemical compound S=C1N=C(C)N=C2NNC=C21 UKMWOQXXGRBQLC-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000005070 ripening Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OCEQBYVMMNGTIV-UHFFFAOYSA-N 6-methyl-1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one Chemical compound O=C1N=C(C)N=C2NNC=C21 OCEQBYVMMNGTIV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 206010034960 Photophobia Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 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
- 208000013469 light sensitivity Diseases 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical group C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YYRHGCUWQUHJFR-UHFFFAOYSA-N n-(4-cyano-1h-pyrazol-5-yl)acetamide Chemical compound CC(=O)NC=1NN=CC=1C#N YYRHGCUWQUHJFR-UHFFFAOYSA-N 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-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
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- YYECQADENGBYLX-UHFFFAOYSA-N 6-chloro-1,2-dihydropyrazolo[3,4-d]pyrimidine-4-thione Chemical compound S=C1N=C(Cl)N=C2NNC=C21 YYECQADENGBYLX-UHFFFAOYSA-N 0.000 description 1
- DOMOUWJGODANHH-UHFFFAOYSA-N 6-methyl-1h-pyrazolo[3,4-d]pyrimidine Chemical compound CC1=NC=C2C=NNC2=N1 DOMOUWJGODANHH-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000287433 Turdus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LIXKZGGCFHBXNJ-UHFFFAOYSA-N methylsulfanylformic acid Chemical compound CSC(O)=O LIXKZGGCFHBXNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 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
- 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 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- the present invention relates to photographic materials comprising light-sensitive silver halide emulsions. More particularly, this invention is directed to stabilized silver halide emulsions which have less tendency to fog and which still possess substantially the same light sensitivity.
- Fogging in general, and chemical fogging in particular may be defined as a uniform deposit of silver extending over and either partially or wholly obliterating the image and is caused in a number of Ways namely, the nature of the emulsion, its age and the conditions under which it has been stored, the nature of the developer, impurities in the developing solution and the time and temperature of the development.
- chemical fogging is promoted when such active agents as metal are employed in a concentrated solution or are used in the presence of an excess of alkali.
- the oxidation of certain developing agents such as metol and hydroquinone exerts a powerful fogging action.
- R represents a hydrogen atom, alkyl groups containing from one to eighteen carbon atoms, aromatic groups and halogen and X-represents a hydrogen atom, a carboxyalkyl group or the roup S-A wherein A represents the pyrazolopyrimidine structure shown above.
- the antifogging effect is generally due to the presence in the emulsion of the pyrazolopyrimidine structure and not necessarily to the size of configuration of substituents R and X.
- R represents an alkyl group
- substituents wherein R represents an alkyl group include groups such as methyl, ethyl propyl. butyl, hexyl, octyl, decyl, dodecyl, octadecyl and the like.
- the substituent R can also represent aromatic radicals such as phenyl, naphthyl and anthryl radicals as well as a halogen atom such as chlorine.
- the substituent X can represent a hydrogen atom, a halo radical such as a chloro radical, carboxy-allcyl radicals such as carboxymethyl, carboxyethyl, carboxybutyl and carboxyhexyl radicals, and the disulfides corresponding thereto.
- the antifogging agents which have been found to exert such beneficial effects to light-sensitive silver halide emulsions for the prevention of chemical fogging can be readily prepared in accordance with known procedures. such as described in J. Am. Chem. Soc, vol. 79, 6407-15 (1957).
- 4-mercapto-6-methyl pyrazolo (3,4-d) pyrimidine is conveniently prepared by reacting under refiux conditions S-aminoi-cyanopyrazole with acetic anhydride to provide 5-acetylamino-4-cyanopyrazole which is subsequently reacted with potassium hydroxide and hydrogen peroxide to yield 4-hydroxy-6-methyl pyrazolo (3,4-d) pyrimidine.
- the hydroxide is then converted to the mercapto derivative by reaction with phosphorous pentasulfide.
- the addition of the antifoggants can be made before, during or after the addition of the soluble silver salt to the soluble halide in the presence of a suitable carrier or colloid such as gelatin, polyvinyl alcohol, solubilized casein, albumin and the like.
- the antifoggants of the present invention can also be employed as components of the developing solution.
- the amount of antifogging agent employed as additives to the light-sensitive emulsions varies from about 0.1 to about 50 milligrams of antifoggant per 0.6 mole of silver halide.
- antifogging agents When the antifogging agents are employed as ripening finals it has been found advantageous to employ them in amounts in the range of from about 0.1 to about 25 milligrams per 0.6 mole of silver halide whereas when the antifogging agents are employed in coating finals it has been found advantageous to employ amounts in the range of from about 0.5 to about 50 milligrams of antifoggant per 0.6 mole of silver halide.
- the development of optimum characteristics within the range set forth above will depend, in part, upon the type of,
- the antifogging agents of the invention in adjacent layers, for example, in a separate undercoating layer or in the antiabrasion gelatin surface.
- antifogging agents of the invention can be compatibly employed in combination with other known antifoggants and stabilizers; with sulfur-, reduction and 1netal-, and noble metal sensitizers as well as in combination with polyoxyalkylene polyols, their derivatives; polyvinylpyrrolidones and other accelerators.
- 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 0.1% solution of 4-mercapto-6-anethylpyrazolo (3,4-d) pyrimidine was prepared and added to the emulsion as an antifoggant and stabilizer. The emulsion samples contained about 0.6 mole of silver halide. The so prepared emulsion samples were coated on a suitable cellulose ester base' and dried. Samples of these film coatings where then G exposed in a Type 113 'sensitomete-r and developed in a developer of the following composition:
- the stabilizer used in this example was prepared as follows:
- Example II The procedure used was the same as in Example I except that there was used as the stabilizer 4-carboxymethyl thioether of the 6-methyl-pyrazolo (3,4-d) pyrimidine. The results of the experiment indicated that 80 milligrams of the compound provided the same effectiveness as 8.0 milligrams of the compound of Example I.
- the carboxymethyl thioether is prepared by heating equimoleoular portions of the mercapto compound and bromoacetic acid and sufiicient 2 N sodium hydroxide solution to take up the hydrogen bromide split-off during the reaction under reflux for two and one-half hours. After cooling the reaction mixture is acidified and yields the compound.
- Example 111 The procedure was the same as Example I except that there was used the disulfide corresponding to 4-mercapto- 6-methyl-pyrazolo (3,4-d) pyrimidine. The results obtained were similar to those obtained in Example I.
- the stabilizer was prepared from the mercapto compound by oxidizing it in ethanol solution with hydrogen peroxide.
- Example IV Exposed samples of a photographic film were developed .for twelve minutes at 65 F. in a standard metol-hydroquinone developer. Two tests were made, one with the normal developing solution and one with a developer containing 200 m'gs. of 4-mercapto-6-methyl-pyrazolo (3,4-d) pyrimidine to 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.
- a light-sensitive photographic material comprising a light-sensitive silver halide emulsion, a carrier therefor and an antifogging agent characterized by the general formula:
- a light-sensitive photographic material comprising a light-sensitive silver halide emulsion, a carrier therefor, said emulsion containing, as an antifog-gant, 4-mercapto- 6-methyl-pyrazolo (3,4-d) pyrimidine.
- a light-sensitive photographic material comprising a light-sensitive silver halide emulsion, a carrier therefor, said emulsion containing, as an antifoggant, 4-mercapto- 6-chloro-pyrazolo (3,4-d) pyrimidine.
- a light-sensitive photographic material comprising a light-sensitive silver halide emulsion, a carrier therefor, said emulsion containing, as an antifoggant, a compound of the formula:
- a light-sensitive photographic material comprising a light-sensitive silver halide emulsion, a carrier therefor, said emulsion containing, as an antifoggant, a compound of the formula:
- R is the same as the radical represented by R in the foregoing general formula.
- R represents a member selected firom the group consisting of hydrogen chloro, alkyl aromatic radicals and X represents a member selected from the group consisting of hydrogen, carboxyalkyl radicals containing up to six carbon atoms in the alkyl group and a radical having the formula N ll i N wherein R is the same as the radical represented by R in the foregoing general formula.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE624110D BE624110A (is") | 1961-11-02 | ||
| US149520A US3244521A (en) | 1961-11-02 | 1961-11-02 | Silver halide emulsions containing antifogging agents |
| GB35484/62A GB965047A (en) | 1961-11-02 | 1962-09-18 | Improvements in or relating to silver halide emulsions containing antifogging agents |
| DEG36249A DE1182060B (de) | 1961-11-02 | 1962-10-27 | Verfahren zur Schleierverminderung oder Schleierverhuetung in photographischen Halogen-silber enthaltenden Materialien sowie licht-empfindliche photographische Materialien und Entwickler zur Ausfuehrung des Verfahrens |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US149520A US3244521A (en) | 1961-11-02 | 1961-11-02 | Silver halide emulsions containing antifogging agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3244521A true US3244521A (en) | 1966-04-05 |
Family
ID=22530660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US149520A Expired - Lifetime US3244521A (en) | 1961-11-02 | 1961-11-02 | Silver halide emulsions containing antifogging agents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3244521A (is") |
| BE (1) | BE624110A (is") |
| DE (1) | DE1182060B (is") |
| GB (1) | GB965047A (is") |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4366231A (en) * | 1980-01-17 | 1982-12-28 | Agfa Gevaert Aktiengesellschaft | Photographic material containing a stabilizer, a process for its production, a development process, new pyrazoles, a process for their production and intermediate products |
| US5009990A (en) * | 1987-02-26 | 1991-04-23 | Agfa-Gevaert Aktiengesellschaft | Photographic recording material |
| US5508153A (en) * | 1992-12-09 | 1996-04-16 | Konica Corporation | Composition for developing a black-and-white silver halide photographic light-sensitive material |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1203051A (en) * | 1967-02-15 | 1970-08-26 | Agfa Gevaert Nv | Improvements in or relating to photographic light-sensitive silver halide materials |
| JPS6079348A (ja) * | 1983-10-06 | 1985-05-07 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB701054A (en) * | 1951-04-26 | 1953-12-16 | Ici Ltd | Photographic anti-fogging agents and emulsion stabilisers |
| GB716327A (en) * | 1951-09-05 | 1954-10-06 | Ici Ltd | New heterocyclic compounds |
| US2935404A (en) * | 1958-05-27 | 1960-05-03 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
| US2952539A (en) * | 1958-10-23 | 1960-09-13 | Gen Aniline & Film Corp | Photographic emulsions and developers stabilized with purine compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE874702C (de) * | 1945-12-15 | 1953-04-27 | Gen Aniline & Film Corp | Stabilisatoren fuer photographische Emulsionen |
| DE957183C (de) * | 1953-07-01 | 1957-01-31 | Eastman Kodak Co | Stabilisiertes photographisches Material |
-
0
- BE BE624110D patent/BE624110A/xx unknown
-
1961
- 1961-11-02 US US149520A patent/US3244521A/en not_active Expired - Lifetime
-
1962
- 1962-09-18 GB GB35484/62A patent/GB965047A/en not_active Expired
- 1962-10-27 DE DEG36249A patent/DE1182060B/de active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB701054A (en) * | 1951-04-26 | 1953-12-16 | Ici Ltd | Photographic anti-fogging agents and emulsion stabilisers |
| GB716327A (en) * | 1951-09-05 | 1954-10-06 | Ici Ltd | New heterocyclic compounds |
| US2935404A (en) * | 1958-05-27 | 1960-05-03 | Gen Aniline & Film Corp | Fog reduction in photographic silver halide emulsions |
| US2952539A (en) * | 1958-10-23 | 1960-09-13 | Gen Aniline & Film Corp | Photographic emulsions and developers stabilized with purine compounds |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4366231A (en) * | 1980-01-17 | 1982-12-28 | Agfa Gevaert Aktiengesellschaft | Photographic material containing a stabilizer, a process for its production, a development process, new pyrazoles, a process for their production and intermediate products |
| US5009990A (en) * | 1987-02-26 | 1991-04-23 | Agfa-Gevaert Aktiengesellschaft | Photographic recording material |
| US5508153A (en) * | 1992-12-09 | 1996-04-16 | Konica Corporation | Composition for developing a black-and-white silver halide photographic light-sensitive material |
Also Published As
| Publication number | Publication date |
|---|---|
| GB965047A (en) | 1964-07-29 |
| DE1182060B (de) | 1964-11-19 |
| BE624110A (is") |
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