US3396022A - Quinone stabilizers and antifoggants for silver halide emulsions - Google Patents
Quinone stabilizers and antifoggants for silver halide emulsions Download PDFInfo
- Publication number
- US3396022A US3396022A US467123A US46712365A US3396022A US 3396022 A US3396022 A US 3396022A US 467123 A US467123 A US 467123A US 46712365 A US46712365 A US 46712365A US 3396022 A US3396022 A US 3396022A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- emulsion
- antifoggant
- antifoggants
- compound
- 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
- 229910052709 silver Inorganic materials 0.000 title claims description 25
- 239000004332 silver Substances 0.000 title claims description 25
- -1 silver halide Chemical class 0.000 title claims description 25
- 239000003381 stabilizer Substances 0.000 title claims description 15
- 239000000839 emulsion Substances 0.000 title description 51
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
- 230000005070 ripening Effects 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 5
- 238000007792 addition Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- ZFIQGRISGKSVAG-UHFFFAOYSA-N 4-methylaminophenol Chemical compound CNC1=CC=C(O)C=C1 ZFIQGRISGKSVAG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- IPPWILKGXFOXHO-UHFFFAOYSA-N chloranilic acid Chemical compound OC1=C(Cl)C(=O)C(O)=C(Cl)C1=O IPPWILKGXFOXHO-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910021612 Silver iodide Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- 229940045105 silver iodide Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940001482 sodium sulfite Drugs 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- OXLCLHPJAMQUBP-UHFFFAOYSA-N 2,5-dichloro-3,6-dihydroxycyclohexa-2,5-diene-1,4-dione;sodium Chemical compound [Na].[Na].OC1=C(Cl)C(=O)C(O)=C(Cl)C1=O OXLCLHPJAMQUBP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 229940043349 potassium metabisulfite Drugs 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 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
- 238000001228 spectrum Methods 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
- 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
- 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
-
- 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 the use of anti-fogging and stabilizing agents for photographic silver halide emulsions and, more particularly, to the employment of certain benzoquinone derivatives for such purposes.
- lightsensitive emulsions such as gelatino-silver halide emulsions exhibit a marked tendency to fog.
- the fog may be attributable to a number of influences such as excessive ripening of the emulsion by prolonged storage of the film and especially under elevated conditions of temperature and/or humidity and by prolonged development of the exposed emulsion.
- a primary object of the present invention resides in the provision of improved anti-fogging compounds in which the above disadvantages are eliminated or at least mitigated to a substantial degree.
- a further object of the present invention resides in the provision of light-sensitive emulsions containing a compound which stabilizes the emulsion against fogging while exhibiting little tendency to reduce the speed and/or contrast of the emulsion.
- a still further object of the present invention resides in the provision of light-sensitive emulsions containing a compound which stabilizes the emulsion against fogging while exhibiting little tendency to reduce the sensitivity of the emulsion to light of longer wave length affected by the presence of one or more sensitizing dyes.
- Another object of the present invention resides in the provision of improved silver halide developing compositions containing an antifogging compound whereby there is obtained reduced fog, improved contrast, speed, and stability of photographic emulsions developed therewith.
- X represents halogen e.g., chlorine, bromine, etc.
- R and R represent hydrogen, or a salt-forming cation such as sodium, potassium, barium, lanthanum, silver,
- the compounds encompassed by the above formula maybe prepared for example by treating 2,5-dihydroxy- 3,6-dimethoxy acetophenone with halogen e.g., bromine or chlorine, in acetic acid solution to form the corresponding 3,5-dihalo-2,5 dihydroxybenzoquinone derivative.
- halogen e.g., bromine or chlorine
- the compound produced by the above method may be readily converted to its salt by reaction with a compound containing the desired cation such as sodium carbonate, potassium carbonate, silver nitrate, ammonium carbonate or the like.
- Ripening finals are added during the ripening or the sensitivity increasing stage of the emulsion making process.
- Such additions may be made before, during or after the decomposition of the soluble silver salt such as silver nitrate by means of a soluble halide such as potassium, bromide, sodium chloride or the like in the presence of a colloidal carrier such as gelatin, PVA, solubilized casein, albumen or the like.
- Coating finals are added to the emulsion just prior to coating on a suitable support such as glass, paper or film at a time when the emulsion has nearly attained its maximum sensitivity.
- the antifoggings When used as ripening finals, the antifoggings are best employed in a concentration of 5 to 40 mg. per .6 mole of silver halide and when used as coating finals in a concentration of to 500 mg. per .6 mole of silver halide.
- concentration used depends on the type of emulsion employed and it is advisable to determine the optimum concentration from case to case.
- the :desired result may be procured by addition of the antifoggant and stabilizer to one or several processing baths such as developer, fixer or the like.
- the antifoggants of the present invention may be employed in concentrations ranging from 0.5 gram to 1 gram per liter, e.g. per liter of developer composition with a range of 0.2 gram to 0.5 gram being particularly preferred.
- antifoggants and stabilizers may be utilized 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 employed in combination with other known antifoggants and stabilizers, reductionand nietaland noble metal sensitizers, or in combination with hydroxypolyethanoxy derivatives, i.e., those obtained by reacting ethylene oxide with an alcohol, phenol, amine or the like (see US. Patent 1,970,578).
- Example I illustrates the improvements provided by the present invention when the antifoggant is added directly to a silver halide emulsion.
- 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 position:
- the antifoggant was prepared as follows: 0.5 g. of 2,5-dihydroxy-3,6-dimethoxyacetophenone in 8 cc. of acetic acid was treated with chlorine (0.6 g.) in acetic acid (2 cc.). The mixture was heated on a steam bath for approximately 1 hr. and allowed to cool. A yellow precipitate formed which was removed and crystallized from acetic acid. The product, 2,5-dichloro-3,G-dihydroxyp-benzoquinone formed yellow needles and dried to a red powder. (Reference: J. Amer. Chem. See, p. 1395, (1953).)
- Example II Exposed samples of a photographic film were developed for '12 minutes at 65 F. in a standard metol-hydroquinone developer. Two tests are made, one with the normal developing solution and one with a developer containing 50 milligrams per liter of the antifoggant of Example I.
- Sensitometric strips developed in the normal developer (control) for 12 minutes showed of fog of .30, whereas those strips which were developed in the developer containing the antifoggant, had a fog of .20.
- the following example illustrates the improved results obtained when the antifoggant compound is included in an antiabrasion layer.
- Example III A silver halide emulsion in gelatin containing 2% silver iodide and 98% silver bromide was coated on filmbase in a manner known to the art. After the coating was applied, an aqueous gelatin solution containing grams of gelatin per 1 liter and 50 mg. of 2,5-dichloro-3,6-dihydroxy-p-benzoquinone, prepared in the manner described above, was coated thereon as an antiabrasion layer. After drying, film samples were exposed and processed as described in Example I. The samples exhibited a relative speed of 100 and a fog of .20 compared with a type coating of the above, but lacking the antifoggant, and having a speed of 100 and a fog of .30.
- Example IV Silver chlorobromide emulsions for enlarging paper are prepared according to the formulae described on p. 343 of Photographic Chemistry by Pierre Glafkides, a a Fountain Press Publication 1958.
- Emulsion Fresh Oven Variable Contrast Emulsion
- the developer composition may be any of those conventionally employed in the development of exposed silver halide emulsions and accordingly may be of the hydroquinone type, i.e., those which contain hydroquinone, potassium metabisulfite and potassium bromide, or they may be of the metol-hydroquinone type, i.e., those which contain p-methylaminophenol, sodium sulfite, sodium 'bisulfite, hydroquinone, sodium carbonate, and potassium bromide.
- the developer composition may be of the so-called borax type, i.e., those which contain p-methylaminophenol, sodium sulfite, hydroquinone, borax and potassium bromide.
- the improvement in the fog characteristic made possible by the antifoggants of the present invention does not entail any adverse etfects upon any of the other photographic properties of the silver halide emulsion such as D Max, contrast, speed and the like.
- a light-sensitive silver halide emulsion containing an antifoggant and stabilizer comprising a compound of the following general formula:
- X represents halogen and R and R are selected from the group consisting of hydrogen and a cation.
- a light-sensitive photographic material comprising a base and a light-sensitive silver halide emulsion, said light-sensitive material containing an antifoggant and stabilizer comprising a compound of the following general formula:
- RO/WX X L/OR ll wherein X represents halogen and R and R are selected from the group consisting of hydrogen and a cation.
- An aqueous developer solution containing a silver halide photographic developing agent and an antifoggant and stabilizer comprising a compound of the following general formula:
- X represents halogen and R and R are selected from the group consisting of hydrogen and a cation.
- said antifoggant comprises 2,5-dichloro-3,6-dihydroxy-p-benzoquinone.
- a process for the preparation of a photographic emulsion having a reduced tendency to fog which comprises forming the emulsion, ripening the emulsion and, during said ripening, adding thereto an antifoggant and stabilizer comprising a compound of the following general formula:
- X represents halogen and R and R are selected from the group consisting of hydrogen and a cation.
- a process for the preparation of a photographic emulsion having a reduced tendency to fog which comprises forming the emulsion, ripening the emulsion, coating said emulsion on a base and adding to said emulsion just prior to the coating thereof on the base an antifoggant and stabilizer comprising a compound of the following general formula:
- X represents halogen and R and R are Selected from the group consisting of hydrogen and a cation.
- Light-sensitive photographic material comprising a base, a light-sensitive silver halide emulsion layer, and an anti-abrasion layer containing an antifoggant and stabilizer comprising a compound of the following general formula:
- X represents halogen and R and R are selected from the group consisting of hydrogen and a cation.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL134366D NL134366C (forum.php) | 1965-06-25 | ||
| US467123A US3396022A (en) | 1965-06-25 | 1965-06-25 | Quinone stabilizers and antifoggants for silver halide emulsions |
| GB26513/66A GB1146719A (en) | 1965-06-25 | 1966-06-14 | Improvements in or relating to photographic emulsions |
| DE19661547910 DE1547910A1 (de) | 1965-06-25 | 1966-06-21 | Verfahren zur Behandlung von lichtempfindlichen Silberhalogenid-Emulsionen sowie lichtempfindliche Silberhalogenid-Emulsionen |
| NL6608570A NL6608570A (forum.php) | 1965-06-25 | 1966-06-21 | |
| FR66587A FR1484916A (fr) | 1965-06-25 | 1966-06-23 | Agents anti-voile à base de dérivés de la benzoquinone pour émulsions photographiques |
| BE682993D BE682993A (forum.php) | 1965-06-25 | 1966-06-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US467123A US3396022A (en) | 1965-06-25 | 1965-06-25 | Quinone stabilizers and antifoggants for silver halide emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3396022A true US3396022A (en) | 1968-08-06 |
Family
ID=23854456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US467123A Expired - Lifetime US3396022A (en) | 1965-06-25 | 1965-06-25 | Quinone stabilizers and antifoggants for silver halide emulsions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3396022A (forum.php) |
| BE (1) | BE682993A (forum.php) |
| DE (1) | DE1547910A1 (forum.php) |
| GB (1) | GB1146719A (forum.php) |
| NL (2) | NL6608570A (forum.php) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4010036A (en) * | 1972-06-30 | 1977-03-01 | Konishiroku Photo Industry Co., Ltd. | Lith-type silver halide photosensitive material containing a p-benzoquinone derivative |
| US4175966A (en) * | 1975-08-02 | 1979-11-27 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive black-white silver halide photographic material for forming a high-contrast silver image and method of treating thereof |
| US4202788A (en) * | 1979-02-12 | 1980-05-13 | Eastman Kodak Company | Stabilization of aqueous p-benzoquinones |
| US5290661A (en) * | 1991-07-31 | 1994-03-01 | Fuji Photo Film Co., Ltd. | Method for forming images by silver salt diffusion transfer |
| US5547827A (en) * | 1994-12-22 | 1996-08-20 | Eastman Kodak Company | Iodochloride emulsions containing quinones having high sensitivity and low fog |
-
0
- NL NL134366D patent/NL134366C/xx active
-
1965
- 1965-06-25 US US467123A patent/US3396022A/en not_active Expired - Lifetime
-
1966
- 1966-06-14 GB GB26513/66A patent/GB1146719A/en not_active Expired
- 1966-06-21 NL NL6608570A patent/NL6608570A/xx unknown
- 1966-06-21 DE DE19661547910 patent/DE1547910A1/de active Pending
- 1966-06-23 BE BE682993D patent/BE682993A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4010036A (en) * | 1972-06-30 | 1977-03-01 | Konishiroku Photo Industry Co., Ltd. | Lith-type silver halide photosensitive material containing a p-benzoquinone derivative |
| US4175966A (en) * | 1975-08-02 | 1979-11-27 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive black-white silver halide photographic material for forming a high-contrast silver image and method of treating thereof |
| US4202788A (en) * | 1979-02-12 | 1980-05-13 | Eastman Kodak Company | Stabilization of aqueous p-benzoquinones |
| US5290661A (en) * | 1991-07-31 | 1994-03-01 | Fuji Photo Film Co., Ltd. | Method for forming images by silver salt diffusion transfer |
| US5547827A (en) * | 1994-12-22 | 1996-08-20 | Eastman Kodak Company | Iodochloride emulsions containing quinones having high sensitivity and low fog |
Also Published As
| Publication number | Publication date |
|---|---|
| BE682993A (forum.php) | 1966-12-01 |
| NL134366C (forum.php) | |
| GB1146719A (en) | 1969-03-26 |
| NL6608570A (forum.php) | 1966-12-27 |
| DE1547910A1 (de) | 1969-12-18 |
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