US2735765A - Ch-chs - Google Patents
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- US2735765A US2735765A US2735765DA US2735765A US 2735765 A US2735765 A US 2735765A US 2735765D A US2735765D A US 2735765DA US 2735765 A US2735765 A US 2735765A
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- United States
- Prior art keywords
- color
- antistain
- agent
- incorporated
- emulsion
- 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
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- 239000003795 chemical substances by application Substances 0.000 claims description 42
- 239000000839 emulsion Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 24
- -1 SILVER HALIDE Chemical class 0.000 claims description 19
- 229910052709 silver Inorganic materials 0.000 claims description 16
- 239000004332 silver Substances 0.000 claims description 16
- 230000003647 oxidation Effects 0.000 claims description 11
- 238000007254 oxidation reaction Methods 0.000 claims description 11
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000010410 layer Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- ZZXILYOBAFPJNS-UHFFFAOYSA-N 2-octylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=CC=C1O ZZXILYOBAFPJNS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 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
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZBJNNOTWURHXIS-UHFFFAOYSA-N 1,4-dimethoxy-2-octadecylbenzene Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(OC)=CC=C1OC ZBJNNOTWURHXIS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical group CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000084 colloidal system Substances 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
- 230000000694 effects Effects 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
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- CLDZVCMRASJQFO-UHFFFAOYSA-N 2,5-bis(2,4,4-trimethylpentan-2-yl)benzene-1,4-diol Chemical compound CC(C)(C)CC(C)(C)C1=CC(O)=C(C(C)(C)CC(C)(C)C)C=C1O CLDZVCMRASJQFO-UHFFFAOYSA-N 0.000 description 1
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 1
- KHZCDSSLAQEJBH-UHFFFAOYSA-N 2-(aminomethyl)benzene-1,4-diol Chemical compound NCC1=CC(O)=CC=C1O KHZCDSSLAQEJBH-UHFFFAOYSA-N 0.000 description 1
- ZRADTNJSPQDCDV-UHFFFAOYSA-N 2-butyl-4-methoxyphenol Chemical compound CCCCC1=CC(OC)=CC=C1O ZRADTNJSPQDCDV-UHFFFAOYSA-N 0.000 description 1
- JSBJPJNIQHDYEN-UHFFFAOYSA-N 3-(7-azabicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)-7-azabicyclo[4.2.0]octa-1(6),2,4-triene Chemical group C1C=2C=C(C=CC=2N1)C1=CC2=C(NC2)C=C1 JSBJPJNIQHDYEN-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- QSYOBRLVRMIBRU-UHFFFAOYSA-N 4-(4,5-dihydro-1h-imidazol-2-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NCCN1 QSYOBRLVRMIBRU-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 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
- 125000003277 amino group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 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
- 238000001914 filtration Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-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
- 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.
- color-forming or coupler compounds combine with the development product of aromatic amino photographic developers to produce dyes.
- 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 No. 1,102,028, granted June 30, 1914, or they may be incorporated in a waterpermeable medium which is insoluble in the carrier for the sensitive silver salt as described in Mannes 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 difliculty frequently encountered in these processes is the formation of color fog or stain.
- dye fog is frequently formed in the emulsion layer. This is because the developing agent has been oxidized to some extent by the action of the air and the oxidized developer tends to couple with the color-forming compound at places in the photographic material where no silver image is produced. It is well known that in these processes the dye should beformed only where the silver halide is reduced to metallic silver, thereby oxidizing the developing agent to a form which couples with the color former. Once the developing agent is oxidized, it couples immediately with the color former whether a photographic image is present or not.
- Aerial oxidation of the developer or oxidation by means other than the photographic image therefore converts the developer to a form which will immediately react with the color former to produce a color fog on stain.
- This effect is especially noticeable in materials having couplers incorporated in the sensitive layer since there is no coupler in the developing solution to react with any developing agent which is oxidized by the action of the air. Fog or stain arising from these causes is not readily controlled by the same procedures used to control silver fog.
- a further object is to provide antistain agents which are easily compatible with and non-difiusing in the colloid of the photographic layer in which they are incorporated.
- a further object is to provide antistain agents which are non-diffusing in the photographic layer and which are strong enough reducing agents to react rapidly with oxidized color de- 5 veloper.
- 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 bath.
- This compound was prepared by demethylating 1,1- methylene bis(2,5-dimethoxy-4-octadecylbenzene) with AlC13 in boiling dry benzene.
- Aluminum chloride 20 g. (fine powder) g. of the dimethoxy intermediate, and 200 ml. of dry benzene were refluxed on a steam bath with eflective mechanical stirring for 20 hours.
- the cooled reaction mixture was poured into 1500 ml. of cold methyl alcohol, and the solid obtained was crystallized twice from ethyl acetate, using carbon decolorizing the first time. There was obtained 5.5 g. of colorless material (going pink on standing), having a melting point of 190-191 C.
- This compound was prepared by the method given for 2,2-isobutylidene bis(5-tert-butyl-4-methoxyphenol) substituting 4-rnethoxyphenol for 2-tert-butyl-4-methoxyphenol.
- This compound was prepared by the method given for 2,2-methylene bis(5-tert-butyl-4-methoxyphenol), substituting isobutyraldehyde for formaldehyde.
- the product is a white crystal line material melting at 181.5- 183.5 C.
- the 4,4'-bis(2,5-dihydroxybenzalamino)diphenyl prepared above was reduced in dioxane solution, using Raney nickel as a catalyst and 40-50 pounds of hydrogen pressure at 60-65 C.
- the catalyst was removed from the hot solution by filtration and the solution cooled.
- the product formed was filtered, washed with a small volume of fresh dioxane, and crystallized twice from the same solvent.
- the (2,5-dihydroxybenzyl)benzidine was obtained almost colorless but turned light brown in the open air. It melts at 198-200 C.
- 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 the molar equivalent of 0.05 g. of 2,5-di-tert. octyl hydroquinone 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 support so that the antistain agent was equivalent to 5 mg. per square foot of 2,5-di-tert. octyl hydroquinone.
- Two check coatings were made: One containing no antistain agent, and one containing 5 mg. per square foot of 2,5-di-tert. octyl hydroquinone.
- the film strips were exposed on a Ib sensitorneter using a silver wedge varying in density from 0 to 3. They were then developed 10 minutes at 68 F. in the following developer:
- Compounds 4, and 7 caused no more fading of the cyan dye than the check coating without antistain agent, and compounds 1, 6 and 7 caused even less fading of the yellow dye than the check coating free of antistain agent, that is, these cornpounds caused some increase in density of yellow dye as well as improving antistain properties.
- Another compound useful as an anti-stain agent in photographic emulsions is 2-p-cyanophenyl-2-imidazoline.
- the antistain agents of our invention may also he 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 espe cially 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 developing agent and as an antistain agent a bihydroquinone having the formula (BR OR where R is selected from the class consisting of hydrogen and a methyl radical, R is selected from the class consisting of hydrogen and a methyl radical, X is selected from the class consisting of hydrogen and amino group and an alkyl group having from 1 to 18 carbon atoms, and Z is selected from the class consisting of methylene, isobutylene and N,N'-dimethylenebenzidine groups and a single chemical bond.
- a color-forming photographic emulsion having reduced fogging tendency comprising a silver halide emulsion having incorporated therein a non-difiusing coupler compound capable of coupling with the oxidation prodduct of a primary aromatic amino developing agent and as an antistain agent a bihydroquinone having the formula (I)H OH OH OH in which R is an alkyl group of from 1 to 18 carbon atoms.
- 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 developing agent and as an antistain agent a bihydroquinone having the formula CH; OCH:
- R is an alkyl group of from 1 to 18 carbon atoms.
- 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 developing agent and as an antistain agent a bihydroquinone.
- 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 developing agent and as an antistain agent 2,2-methylene bis(5-tert. butyl-4-methoxyphenol.
- a color-forming photographic emulsion having reduced fogging tendency comprising a. silver halide emulsion having incorporated therein a non-ditfusing coupler compound capable of coupling with the oxidation prodnot of a primary aromatic amino developing agent and as an antistain agent 2,2-methylene bis-S-n-octyl hydroqumone.
- 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 developing agent and as an antistain agent 1,1'-methylene bis(2,S-dimethoxy-4- octadecylbenzene).
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US752148XA | 1953-06-03 | 1953-06-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2735765A true US2735765A (en) | 1956-02-21 |
Family
ID=22124290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2735765D Expired - Lifetime US2735765A (en) | 1953-06-03 | Ch-chs |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2735765A (enrdf_load_html_response) |
| BE (1) | BE529274A (enrdf_load_html_response) |
| FR (1) | FR1110296A (enrdf_load_html_response) |
| GB (1) | GB752148A (enrdf_load_html_response) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955038A (en) * | 1957-07-16 | 1960-10-04 | Du Pont | Sensitized silver halide emulsions |
| US3022167A (en) * | 1957-03-28 | 1962-02-20 | Polaroid Corp | Photographic products, processes and compositions |
| US3022166A (en) * | 1957-03-28 | 1962-02-20 | Polaroid Corp | Photographic products, processes and compositions |
| US3482971A (en) * | 1967-07-24 | 1969-12-09 | Polaroid Corp | Scavengers for oxidized developing agent |
| US3970707A (en) * | 1974-04-11 | 1976-07-20 | Vasily Ivanovich Shvedov | Method for preparing 3,5,3',5'-tetrabromo-2,4,2',4'-tetraoxydiphenyl |
| DE2839434A1 (de) * | 1977-09-12 | 1979-03-15 | Konishiroku Photo Ind | Farbphotographisches aufzeichnungsmaterial |
| US4174220A (en) * | 1976-10-30 | 1979-11-13 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye fading inhibitors |
| US4178184A (en) * | 1976-10-23 | 1979-12-11 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye-fading inhibitors |
| US4192682A (en) * | 1977-01-26 | 1980-03-11 | Konishiroku Photo Industry Co., Ltd. | Process of forming a high-contrast silver image |
| FR2445542A1 (fr) * | 1978-12-28 | 1980-07-25 | Fuji Photo Film Co Ltd | Materiau photographique contenant un coupleur 3-anilino-5-pyrazolone et presentant une resistance a la lumiere amelioree |
| US4268621A (en) * | 1978-07-29 | 1981-05-19 | Konishiroku Photo Industry Co., Ltd. | Direct positive photographic material |
| US4362795A (en) * | 1979-08-29 | 1982-12-07 | Fuji Photo Film Co., Ltd. | Process for forming photographic images and photographic light-sensitive material for use therein |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| US4536466A (en) * | 1983-03-30 | 1985-08-20 | Fuji Photo Film Co., Ltd. | Heat developable element with stabilizer |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US4713317A (en) * | 1984-05-22 | 1987-12-15 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material |
| US4824771A (en) * | 1986-12-18 | 1989-04-25 | Eastman Kodak Company | Photographic acetanilide couplers with novel ballast group and photographic elements containing them |
| JPH0258047A (ja) * | 1988-08-24 | 1990-02-27 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JPH02118639A (ja) * | 1988-10-28 | 1990-05-02 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| EP0355818A3 (en) * | 1988-08-24 | 1990-08-01 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US4983506A (en) * | 1987-10-14 | 1991-01-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5063135A (en) * | 1989-02-27 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Color diffusion transfer photographic light-sensitive material |
| US5104774A (en) * | 1989-04-10 | 1992-04-14 | Fuji Photo Film Co., Ltd. | Image forming method |
| US5126234A (en) * | 1988-08-12 | 1992-06-30 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide color photographic material |
| US5156945A (en) * | 1989-02-21 | 1992-10-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| US5264332A (en) * | 1990-10-08 | 1993-11-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0601836A2 (en) | 1992-12-07 | 1994-06-15 | Konica Corporation | Silver halide light sensitive color photographic material |
| US5427891A (en) * | 1990-05-17 | 1995-06-27 | Fuji Photo Film Co., Ltd. | Method for developing a silver halide photographic material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US6479198B2 (en) * | 2000-02-01 | 2002-11-12 | Fuji Photo Film Co., Ltd. | Silver halide light-sensitive material containing tanning developing agent |
| CN115716779A (zh) * | 2022-11-28 | 2023-02-28 | 南京工业大学 | 一种腰果酚基双元酚及其制备方法与应用 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68923408T2 (de) * | 1988-07-21 | 1995-12-14 | Fuji Photo Film Co Ltd | Lichtempfindliches Farbmaterial. |
| JPH02234158A (ja) * | 1989-03-07 | 1990-09-17 | Fuji Photo Film Co Ltd | カラー感光材料 |
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
- US US2735765D patent/US2735765A/en not_active Expired - Lifetime
- BE BE529274D patent/BE529274A/xx unknown
-
1954
- 1954-06-02 GB GB16321/54A patent/GB752148A/en not_active Expired
- 1954-06-02 FR FR1110296D patent/FR1110296A/fr 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 (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3022167A (en) * | 1957-03-28 | 1962-02-20 | Polaroid Corp | Photographic products, processes and compositions |
| US3022166A (en) * | 1957-03-28 | 1962-02-20 | Polaroid Corp | Photographic products, processes and compositions |
| US2955038A (en) * | 1957-07-16 | 1960-10-04 | Du Pont | Sensitized silver halide emulsions |
| US3482971A (en) * | 1967-07-24 | 1969-12-09 | Polaroid Corp | Scavengers for oxidized developing agent |
| US3970707A (en) * | 1974-04-11 | 1976-07-20 | Vasily Ivanovich Shvedov | Method for preparing 3,5,3',5'-tetrabromo-2,4,2',4'-tetraoxydiphenyl |
| US4178184A (en) * | 1976-10-23 | 1979-12-11 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye-fading inhibitors |
| US4174220A (en) * | 1976-10-30 | 1979-11-13 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye fading inhibitors |
| US4192682A (en) * | 1977-01-26 | 1980-03-11 | Konishiroku Photo Industry Co., Ltd. | Process of forming a high-contrast silver image |
| FR2402892A1 (fr) * | 1977-09-12 | 1979-04-06 | Konishiroku Photo Ind | Produit stabilisateur pour images photographiques en couleur |
| DE2839434A1 (de) * | 1977-09-12 | 1979-03-15 | Konishiroku Photo Ind | Farbphotographisches aufzeichnungsmaterial |
| US4314011A (en) * | 1977-09-12 | 1982-02-02 | Konishiroku Photo Industry Co., Ltd. | Color photographic material |
| US4254216A (en) * | 1977-09-12 | 1981-03-03 | Konishiroku Photo Industry Co., Ltd. | Color photographic material |
| US4268621A (en) * | 1978-07-29 | 1981-05-19 | Konishiroku Photo Industry Co., Ltd. | Direct positive photographic material |
| US4273864A (en) * | 1978-12-28 | 1981-06-16 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive materials |
| FR2445542A1 (fr) * | 1978-12-28 | 1980-07-25 | Fuji Photo Film Co Ltd | Materiau photographique contenant un coupleur 3-anilino-5-pyrazolone et presentant une resistance a la lumiere amelioree |
| US4362795A (en) * | 1979-08-29 | 1982-12-07 | Fuji Photo Film Co., Ltd. | Process for forming photographic images and photographic light-sensitive material for use therein |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| US4536466A (en) * | 1983-03-30 | 1985-08-20 | Fuji Photo Film Co., Ltd. | Heat developable element with stabilizer |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0218266A2 (en) | 1984-05-02 | 1987-04-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US4713317A (en) * | 1984-05-22 | 1987-12-15 | Konishiroku Photo Industry Co., Ltd. | Silver halide color photographic material |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| US4824771A (en) * | 1986-12-18 | 1989-04-25 | Eastman Kodak Company | Photographic acetanilide couplers with novel ballast group and photographic elements containing them |
| US4983506A (en) * | 1987-10-14 | 1991-01-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5126234A (en) * | 1988-08-12 | 1992-06-30 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide color photographic material |
| EP0355818A3 (en) * | 1988-08-24 | 1990-08-01 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| JP2533795B2 (ja) | 1988-08-24 | 1996-09-11 | 富士写真フイルム株式会社 | ハロゲン化銀カラ―写真感光材料 |
| US4988613A (en) * | 1988-08-24 | 1991-01-29 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| JPH0258047A (ja) * | 1988-08-24 | 1990-02-27 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| JPH02118639A (ja) * | 1988-10-28 | 1990-05-02 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の処理方法 |
| JP2549304B2 (ja) | 1988-10-28 | 1996-10-30 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料の処理方法 |
| US5156945A (en) * | 1989-02-21 | 1992-10-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| US5063135A (en) * | 1989-02-27 | 1991-11-05 | Fuji Photo Film Co., Ltd. | Color diffusion transfer photographic light-sensitive material |
| US5104774A (en) * | 1989-04-10 | 1992-04-14 | Fuji Photo Film Co., Ltd. | Image forming method |
| US5427891A (en) * | 1990-05-17 | 1995-06-27 | Fuji Photo Film Co., Ltd. | Method for developing a silver halide photographic material |
| US5264332A (en) * | 1990-10-08 | 1993-11-23 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0601836A2 (en) | 1992-12-07 | 1994-06-15 | Konica Corporation | Silver halide light sensitive color photographic material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US6479198B2 (en) * | 2000-02-01 | 2002-11-12 | Fuji Photo Film Co., Ltd. | Silver halide light-sensitive material containing tanning developing agent |
| EP1124157A3 (en) * | 2000-02-01 | 2003-08-13 | Fuji Photo Film Co., Ltd. | Silver halide light-sensitive material containing tanning developing agent |
| CN115716779A (zh) * | 2022-11-28 | 2023-02-28 | 南京工业大学 | 一种腰果酚基双元酚及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1110296A (fr) | 1956-02-10 |
| GB752148A (en) | 1956-07-04 |
| BE529274A (enrdf_load_html_response) |
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