US2732300A - Unsymmetrical dialkyl hydroquinone - Google Patents
Unsymmetrical dialkyl hydroquinone Download PDFInfo
- Publication number
- US2732300A US2732300A US2732300DA US2732300A US 2732300 A US2732300 A US 2732300A US 2732300D A US2732300D A US 2732300DA US 2732300 A US2732300 A US 2732300A
- Authority
- US
- United States
- Prior art keywords
- color
- hydroquinone
- solution
- emulsion
- incorporated
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims description 13
- 239000000839 emulsion Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 229910052709 silver Inorganic materials 0.000 claims description 13
- 239000004332 silver Substances 0.000 claims description 13
- -1 SILVER HALIDE Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000975 dye Substances 0.000 description 13
- 239000010410 layer Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
- ZZXILYOBAFPJNS-UHFFFAOYSA-N 2-octylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=CC=C1O ZZXILYOBAFPJNS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000001914 filtration 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
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BGAHCCPZJDMEJY-UHFFFAOYSA-N 1-(2-hydroxy-5-methoxy-3-methylphenyl)hexadecan-1-one Chemical compound COC1=CC(=C(C(=C1)C(CCCCCCCCCCCCCCC)=O)O)C BGAHCCPZJDMEJY-UHFFFAOYSA-N 0.000 description 1
- PMWJOLLLHRDHNP-UHFFFAOYSA-N 2,3-dioctylbenzene-1,4-diol Chemical compound CCCCCCCCC1=C(O)C=CC(O)=C1CCCCCCCC PMWJOLLLHRDHNP-UHFFFAOYSA-N 0.000 description 1
- HUYSCRCIPIWDPL-UHFFFAOYSA-N 2,3-dipentylbenzene-1,4-diol Chemical compound CCCCCC1=C(O)C=CC(O)=C1CCCCC HUYSCRCIPIWDPL-UHFFFAOYSA-N 0.000 description 1
- HINXRUYNUJLKSX-UHFFFAOYSA-N 2-hexadecyl-5-methylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCCCCCC1=CC(O)=C(C)C=C1O HINXRUYNUJLKSX-UHFFFAOYSA-N 0.000 description 1
- PCVPAPVOMWIANY-UHFFFAOYSA-N 2-hexadecyl-6-methylbenzene-1,4-diol Chemical compound CCCCCCCCCCCCCCCCC1=CC(O)=CC(C)=C1O PCVPAPVOMWIANY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PKDVWOVKDPEBQF-UHFFFAOYSA-N 4-methoxy-2-methylphenol Chemical compound COC1=CC=C(O)C(C)=C1 PKDVWOVKDPEBQF-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 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
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate 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
- 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
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/39212—Carbocyclic
- G03C7/39216—Carbocyclic with OH groups
Definitions
- This invention relates to color photography and ,particularly to a method for preventing the formation of color fog or stain in photographic emulsions.
- the method .of .color photography in which colorforming or coupler compounds combine with the development product of aromatic amino photographic developers to produce dyes is wellknown.
- the color formers or couplers may be added directly -to the emulsion layers or may be incorporated in the developing solution as described in Fischer U. S. Patent 1,102,028, granted June 30, 1914, or they may be incorporated in a water-permeable medium which is insoluble in the carrier for the sensitive silver salt as described in Marines and Godowsky U. S. Patent 2,304,940, December 15, 1942, and Jelley and Vittum U. S. Patent 2,322,027, granted June 15, 1943.
- a difiiculty frequently encountered in these processes is the formation of color fog "or stain.
- This stain which appears in the highlight orwliite .areas of processed pictures, may originate from several diiferent causes.
- One cause may be that a small amount of developing agent is oxidized by the oxygen of theair, producing oxidized developer in small amounts which reacts with the colorforming couplers throughout thewhollepicture area.
- some dye stain is formed.
- An appreciable part of "the dye stain may result from silver fog.
- This compound has good stain preventing propertieswhen incorporated in photographic color films but it suffers from .strong enough reducing agents .to .react rapidly with oxi- .dized color developer.
- a further object is to provide antistain agents which do not form highly colored oxidation products when the material containing them is put through an oxidizing hath.
- R represents an alkyl group tOf :from 1 to 18 carbon atoms, R being a different alkyl group than R and being attached to 'the-hydroquinone in the 5 or 6 position.
- reaction mixture was allowed to stand overnight and was then poured into a solution .of 205 .g. of sodium acetate in 2 liters of water. Mechanicalstirring gave a The latter was decanted and the paste stirred with 1250 cc. petroleum ether until a thick slurry resulted (ca. 15 min). The solid was collected on an 18.5 cm. Biichner funnel and washed with 500 cc. more petroleum ether, followed by 2 liters of water. The material, dried in a steam cabinet at 40 C., weighed 137 g. (75.7%) and contained some inorganic material. Recrystallization from 2400 cc. of ethyl alcohol diluted with 600 cc.
- antistain agents of our invention are useful, in general, with emulsions containing couplers incorporated in the manner described in Mannes and Godowsky U. S. Patent 2,304,940 or Jelley and Vittum U. S. Patent 2,322,027.
- Couplers such as those described in Weissberger U. S. Patent 2,298,443 and Salminen and Weissberger U. S. Patent 2,423,730, when incorporated in this way, produce dyes upon color development which are prone to fading by the action of visible or ultraviolet light, when known antistain agents such as 2,5-di-tert. octyl hydroquinone are used in the emulsion layer. These are the yellow and cyan dyes.
- the magenta dyes such as those formed from couplers described in Loria, Weissberger and Vittum U. S. Patent 2,600,788 are relatively little affected by the known antistain agents upon the action of light.
- a quantity of the antistain agent was dissolved with 0.5 g. of coupler in 1.5 cc. of dibutylphthalate.
- the resulting mixture was passed through a colloid mill three times, and to the resulting dispersion, 32 cc. of a gelatino-silver halide emulsion were added, and the mixture blended and coated on a film sup- G.
- the antistain agents of our invention may also be used in non-sensitive overcoating or filter layers, such as a colloidal silver interlayer of multilayer photographic material.
- the antistain agents of our invention are used in the emulsion or other layer in quantities ranging from 0.07 gram to 4.3 grams per liter of emulsion or gelatin solution. These values are, however, merely illustrative.
- the antistain agents of our invention may be incorporated in a processing solution such as a prebath, first developer bath, or color-forming developer used with color film which is developed with a primary aromatic amino developing agent.
- Our materials are particularly useful with color-forming emulsions coated on paper supports where it is especially important to reduce the minimum or fog densities. This applies both to negative developed paper and to reversal paper as well as to transparency materials.
- a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound capable of coupling with the oxidation product of a primary aromatic amino color developer to form a dye and as an antistain agent an unsymmetrical dialkyl hydroquinone having the formula where R represents an alkyl group of from 2 to 18 carbon atoms and R represents a methyl group, R being attached to the hydroquinone nucleus in a position selected from the class consisting of 5 and 6 positions.
- a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound capable of coupling with the oxidation product of a primary aromatic amino color developer to form a dye and as an antistain agent an unsymmetrical 2,5- dialkyl hydroquinone having the formula where R represents an alkyl group of from 2 to 18 carbon atoms.
- a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diifusing coupler compound capable of coupling with the oxidation product of a primary aromatic amino color developer to form a dye and as an antistain agent 2-n-hexadecyl-5-methyl hydroquinone.
- a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-diffusing coupler compound capable of coupling with the oxidation product of a primary aromatic amino color developer to form a dye and as an antistain agent 2-sec. octadecyl-S-methyl hydroquinone.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35944253A | 1953-06-03 | 1953-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2732300A true US2732300A (en) | 1956-01-24 |
Family
ID=23413803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2732300D Expired - Lifetime US2732300A (en) | 1953-06-03 | Unsymmetrical dialkyl hydroquinone |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2732300A (fr) |
| BE (1) | BE529275A (fr) |
| FR (1) | FR1141360A (fr) |
| GB (1) | GB752147A (fr) |
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043697A (en) * | 1958-08-27 | 1962-07-10 | Du Pont | Photographic gelatin-n-vinyllactam silver halide emulsions containing phenolic antifoggants |
| US3148997A (en) * | 1963-01-04 | 1964-09-15 | Dow Chemical Co | Catechol compounds in improving clays and clay-containing materials |
| US3424821A (en) * | 1967-07-20 | 1969-01-28 | Uniroyal Inc | Di(higher secondary alkylated) hydroquinone antioxidants |
| JPS5112250B1 (fr) * | 1970-03-06 | 1976-04-17 | ||
| US3953531A (en) * | 1973-12-19 | 1976-04-27 | Fuji Photo Film Co., Ltd. | Alkylhydroquinone and process for producing the same |
| US4179293A (en) * | 1977-08-09 | 1979-12-18 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4232114A (en) * | 1976-05-31 | 1980-11-04 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive elements containing anti-color fogging agents |
| DE3021207A1 (de) * | 1979-06-04 | 1980-12-11 | Konishiroku Photo Ind | Lichtempfindliches (farb)photographisches aufzeichnungsmaterial |
| JPS5689739A (en) * | 1972-11-20 | 1981-07-21 | Eastman Kodak Co | Photographic element |
| US4377634A (en) * | 1977-09-06 | 1983-03-22 | Fuji Photo Film Co., Ltd. | Method for forming high contrast photographic image |
| US4419529A (en) * | 1981-03-05 | 1983-12-06 | Riedel-De Haen Aktiengesellschaft | Process for the preparation of a 2-alkylphenol |
| EP0112162A2 (fr) | 1982-12-13 | 1984-06-27 | Konica Corporation | Matériel photographique photosensible aux halogénures d'argent |
| EP0147854A2 (fr) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Matériel photosensible aux hologènures d'argent |
| EP0209118A2 (fr) | 1985-07-17 | 1987-01-21 | Konica Corporation | Matériau photographique à l'halogénure d'argent |
| EP0228084A2 (fr) | 1985-12-25 | 1987-07-08 | Fuji Photo Film Co., Ltd. | Procédé de préparation d'une image |
| EP0256537A2 (fr) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Epreuve couleur et méthode pour sa production |
| US5198517A (en) * | 1991-08-06 | 1993-03-30 | Eastman Kodak Company | Polymeric scavengers for oxidized developing agents and photographic elements containing the same |
| US5264332A (en) * | 1990-10-08 | 1993-11-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5434041A (en) * | 1993-04-02 | 1995-07-18 | Eastman Kodak Company | Photographic elements containing particular color couplers in combination with hydroquinone type stabilizers |
| EP0800113A2 (fr) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Marériau photographique couleur à l'halogénure d'argent sensible à la lumière |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2360290A (en) * | 1941-07-31 | 1944-10-10 | Eastman Kodak Co | Preventing formation of color fog in emulsions |
| US2418613A (en) * | 1945-07-30 | 1947-04-08 | Eastman Kodak Co | Fog inhibitors for photographic emulsions |
-
0
- BE BE529275D patent/BE529275A/xx unknown
- US US2732300D patent/US2732300A/en not_active Expired - Lifetime
-
1954
- 1954-06-02 FR FR1141360D patent/FR1141360A/fr not_active Expired
- 1954-06-02 GB GB16320/54A patent/GB752147A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2360290A (en) * | 1941-07-31 | 1944-10-10 | Eastman Kodak Co | Preventing formation of color fog in emulsions |
| US2418613A (en) * | 1945-07-30 | 1947-04-08 | Eastman Kodak Co | Fog inhibitors for photographic emulsions |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043697A (en) * | 1958-08-27 | 1962-07-10 | Du Pont | Photographic gelatin-n-vinyllactam silver halide emulsions containing phenolic antifoggants |
| US3148997A (en) * | 1963-01-04 | 1964-09-15 | Dow Chemical Co | Catechol compounds in improving clays and clay-containing materials |
| US3424821A (en) * | 1967-07-20 | 1969-01-28 | Uniroyal Inc | Di(higher secondary alkylated) hydroquinone antioxidants |
| JPS5112250B1 (fr) * | 1970-03-06 | 1976-04-17 | ||
| JPS5689739A (en) * | 1972-11-20 | 1981-07-21 | Eastman Kodak Co | Photographic element |
| JPS5749895B2 (fr) * | 1972-11-20 | 1982-10-25 | ||
| US3953531A (en) * | 1973-12-19 | 1976-04-27 | Fuji Photo Film Co., Ltd. | Alkylhydroquinone and process for producing the same |
| US4232114A (en) * | 1976-05-31 | 1980-11-04 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive elements containing anti-color fogging agents |
| US4179293A (en) * | 1977-08-09 | 1979-12-18 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4377634A (en) * | 1977-09-06 | 1983-03-22 | Fuji Photo Film Co., Ltd. | Method for forming high contrast photographic image |
| US4277558A (en) * | 1979-06-04 | 1981-07-07 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic materials |
| DE3021207A1 (de) * | 1979-06-04 | 1980-12-11 | Konishiroku Photo Ind | Lichtempfindliches (farb)photographisches aufzeichnungsmaterial |
| US4419529A (en) * | 1981-03-05 | 1983-12-06 | Riedel-De Haen Aktiengesellschaft | Process for the preparation of a 2-alkylphenol |
| EP0112162A2 (fr) | 1982-12-13 | 1984-06-27 | Konica Corporation | Matériel photographique photosensible aux halogénures d'argent |
| EP0147854A2 (fr) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Matériel photosensible aux hologènures d'argent |
| EP0209118A2 (fr) | 1985-07-17 | 1987-01-21 | Konica Corporation | Matériau photographique à l'halogénure d'argent |
| EP0228084A2 (fr) | 1985-12-25 | 1987-07-08 | Fuji Photo Film Co., Ltd. | Procédé de préparation d'une image |
| EP0256537A2 (fr) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Epreuve couleur et méthode pour sa production |
| US5264332A (en) * | 1990-10-08 | 1993-11-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5198517A (en) * | 1991-08-06 | 1993-03-30 | Eastman Kodak Company | Polymeric scavengers for oxidized developing agents and photographic elements containing the same |
| US5434041A (en) * | 1993-04-02 | 1995-07-18 | Eastman Kodak Company | Photographic elements containing particular color couplers in combination with hydroquinone type stabilizers |
| EP0800113A2 (fr) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Marériau photographique couleur à l'halogénure d'argent sensible à la lumière |
Also Published As
| Publication number | Publication date |
|---|---|
| BE529275A (fr) | |
| FR1141360A (fr) | 1957-09-02 |
| GB752147A (en) | 1956-07-04 |
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