US2500487A - Yellow diffusion-fast color formers of the benzimidazole class - Google Patents
Yellow diffusion-fast color formers of the benzimidazole class Download PDFInfo
- Publication number
- US2500487A US2500487A US59203A US5920348A US2500487A US 2500487 A US2500487 A US 2500487A US 59203 A US59203 A US 59203A US 5920348 A US5920348 A US 5920348A US 2500487 A US2500487 A US 2500487A
- Authority
- US
- United States
- Prior art keywords
- parts
- yellow
- sulfonic acid
- octadecylbenzimidazole
- product
- 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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- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- -1 SILVER HALIDE Chemical class 0.000 claims description 23
- 239000000839 emulsion Substances 0.000 claims description 20
- 239000004332 silver Substances 0.000 claims description 10
- 229910052709 silver Inorganic materials 0.000 claims description 10
- 238000009792 diffusion process Methods 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000975 dye Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 238000011161 development Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- JHHVDPLPBJASDF-UHFFFAOYSA-N 2-(4-aminophenyl)-1-octadecylbenzimidazole-5-sulfonic acid Chemical compound N=1C2=CC(S(O)(=O)=O)=CC=C2N(CCCCCCCCCCCCCCCCCC)C=1C1=CC=C(N)C=C1 JHHVDPLPBJASDF-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 2
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001421 myristyl 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])[H] 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
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- IKHMWULQCYUZFW-UHFFFAOYSA-N 3,5-dioxo-n,5-diphenylpentanamide Chemical compound C=1C=CC=CC=1C(=O)CC(=O)CC(=O)NC1=CC=CC=C1 IKHMWULQCYUZFW-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- SZQSTETUIRSWNO-UHFFFAOYSA-N NC=1C=C(C=CC1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O Chemical compound NC=1C=C(C=CC1)C1=NC2=C(N1CCCCCCCCCCCCCCCCCC)C=CC(=C2)S(=O)(=O)O SZQSTETUIRSWNO-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 239000000276 potassium ferrocyanide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 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
- XOGGUFAVLNCTRS-UHFFFAOYSA-N tetrapotassium;iron(2+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] XOGGUFAVLNCTRS-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000002948 undecyl 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])[H] 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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Definitions
- the present invention relates 1 to non-diffusing colorforming components of the Z-phenyl benzimidazole class, having improved solubility characteristics and capable of yielding upon colorforming development yellow dyestuff images-of enhancedspectral characteristicsand exceedingly fine grain.
- the yellow component generally employed is an openchain keto-methylene compound such as acetoacetanilide, benzoyl-acetoacetanilide, and the like.
- an openchain keto-methylene compound such as acetoacetanilide, benzoyl-acetoacetanilide, and the like.
- the dye images produced by such components are satisfactory although they leave something to be desired so far as spectral characteristics and grain are concerned.
- Another disadvantage in the utilization of such components is their low solubility, and particularly'their loW solution stability.
- Photographic emulsions containing yellow color formers of the aforestated type and the processing of such emulsions by color forming development with the formation of improved yellow dye images constitute the purposes and objects of the present invention.
- R is a phenyl radical, a carbon'atom of which is directly linked to the carbon atom of the heterocyclic ring, 1. e-.-,-phenyl;*halogen phenyl, i. e., chlorophenyl, bromophenyl -and the like; alkyl phenyl, i. 6,, toluyl, ethylphenyl and the like; 'alkoxyphenyl, ii-e, 'methoxypnenyl',”emeryphenyl and the like, is the'radi'c'al 'NH.CZCH2.A,
- R2 is an alkyl chain containing at least 10 carbon atoms, i. e., decyl, undecyl, do'decyl, myristyl, tetradecyl, pentadecyl, octadecyl and thelike;
- R3 is a Water solubilizing'group such as sulfo, carboxy'and the'like'A is an alkyloyl radical, i. e., acetyl, propionyl, butyryL'ahd the like,"aroyl ⁇ i.”e., benzoyl, naphthoyl, and the like, cyano or carbethoxy; and his 1 or 2.
- HOaS- The color formers are prepared by heating a 2-(4'-aminophenyl) -1'-long chain alkyl benzimida-zole-5-sulfonic or carboxylic acid with an acyl acetic ester while mixing or by heating the aforesaid components in the presence of pyridine to a temperature of about 100-430 C.
- Emulsions designed for yielding the desired yellow image are prepared by dispersing a small quantity of the color former, i. e., about .5 gram of the color former in 100 cc. of a photographic silver halide emulsion, coating the emulsion on a support and drying the same.
- the film containing the emulsion may be processed by the negative-positive method or by the reversal method while utilizing for color development a primary aromatic amino developer such as p-diethylamino-aniline and the like.
- Example 1 mHm parts of 2-(4'-aminophenyl)-1-octadecylbenzimidazole-5-sulfonic acid and 15 parts of benzoylacetic ester are mixed in a Werner- Pfleiderer and heated for 4 hours at lbs. steam pressure.
- the crude product is purified by taking up in 125 parts of methanol and heating at reflux C.) for 1 hour. After cooling to 30-35 0., the product is collected on a filter, washed with 50 parts of methanol, sucked dry, then air dried.
- the emulsion is coated on a transparent support and dried. After exposure the film is developed in a color forming developer comprising an aqueous solution of 10 parts of sodium sulfite, 15 parts of p-diethylamino aniline, 2.5 parts of sodium carbonate, and '70 parts of potassium bromide. The silver and dye image is thus formed. After removal of the silver by bleaching in potassium ferrocyanide solution and subsequent fixing, a bright yellow dyestufi? image of very fine grain is obtained.
- Example 2 30 parts of 2-(4-aminophenyl)-1-octadecylbenzimidazole-5-sulfonic acid, 15 parts of benzoylacetic ester, and 200 parts of pyridine are heated at 1l0-120 C. for 4 hours.
- the reaction mixture is diluted with 100 parts of water, and then drowned in a mixture of 00 parts of concentrated hydrochloric acid, and 1000 parts of ice-water.
- the crude product is collected on a. filter, Washed twice with cold water, sucked dry as possible, and air dried.
- the crude product is purified by taking up in 200 parts of methanol and heating at reflux (65 C.) for hour. After cooling to 20-25 C., the product is collected on a filter, washed with parts of methanol, sucked dry, then air dried.
- the product is the same as that of Example 1 and may be used as there indicated.
- Example 3 0 181331 1 o Nnooomoo-c HOaS- N/ This product is prepared in the same manner as Example 1 from 30 parts of 2-(3-aminophenyl) 1 octadecylbenzimidazole 5 sulfonic acid, and 15 parts of benzoylacetic ester.
- An intense yellow dye image of very fine grain is obtained by dispersing the color former in a asoaasv photographic silver bromide emulsion and processingthe emulsion as in Example 1.
- Example 4 181131 This product is prepared in the manner of Example 1 from 28 parts of 2-(3',5-diaminophenyl) 1 octadecylbenzimidazole 5 sulfonic acid, and 25 parts of 'benzoylacetic ester.
- Dye images similar to those obtained in Examples 1 and 3 result when utilizing the above color former for the production of an azomethine dye image.
- This product is prepared in the same manner as Example 1 from 30 parts or" 2-[(3-amino-4'- chloro) phenyl]-l-octadecylbenzimidazole-5-sulionic acid, and 15 parts of benzoylacetic ester.
- a bright yellow azomethine dye image is produced by utilizing the above color former as in Example 1. Such dye images are characterized particularly by the fineness of their grain.
- Example 6 I mHa'I This product is prepared in the manner of Example 1 from 32 parts of 2-[(3-amino-4-methoxy) phenyl] 1 octadecylbenzimidazole-5-sulfonic acid, and 18 parts of benzoylacetic ester.
- a bright yellow azomethine dye image is produced by utilizing the above color former as in Example 1. Such dye images are characterized particularly by the fineness of their grain;
- Example 7 1 12 31 This product is prepared in a manner similar to Example 1 from 27 parts of 2-(4'-aminophenyl) 1-octadecylbenzimidazole 5 sulfonic acid, and 15 parts of acetoacetic ester.
- a bright yellow azomethine dye image is produced by utilizing the above color former as in Example 1. Such dye images are characterized particularly by the fineness of their grain.
- This product is prejgiared a manner similar to Example 1 from 27 parts of 2'-(4'-amii'1'ophenyl) --1 octadecylbenzimidazole 5 sul'foni'c acid, and 12 parts of diethyl malon'a'te.
- a bright yellow azomethinedye image is produced by utilizing the above color former as in 37 parts of 2-(4'-aminophenyl)-1-octadecylbenzimidazole-5-sulfonic acid and 50 parts of cyanoacetic ester are heated at 145-150" C. for 4 hours. To the cooled reaction mixture there is added parts of methanol, and 75 parts of ethyl acetate. The product is collected on a filter, washed with '75 parts of ethyl acetate, sucked dry, and then air dried.
- a bright yellow azomethine dye image is produced by utilizing the above color former as in Example 1. Such dye images are characterized particularly by the fineness of their grain.
- R- is a phenyl radical
- R1 is the grouping -NC.CO.CH2.A
- R2 is an alkyl radical containing at least 10 carbon atoms
- R3 is a Water solubilizing group
- n is selected from the class consisting of 1 and 2
- A is a member of the class consisting of alkyloyl, aroyl, cyano and carbethoxy.
- Ra l wherein R is a phenyl radical, R1 is the grouping NH.CO.CH2.A, R2 is an alkyl radical containing at least 10 carbon atoms, R3 is a water solubilizing group, n is selected from the class consisting of 1 and 2, and A is a member of the class consisting of alkyloyl, aroyl, cyano and carbethoxy, and developing the exposed emulsion with a. color forming developer comprising a, primary aromatic amino developer.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR998985D FR998985A (en]) | 1948-11-09 | ||
| BE492063D BE492063A (en]) | 1948-11-09 | ||
| US59203A US2500487A (en) | 1948-11-09 | 1948-11-09 | Yellow diffusion-fast color formers of the benzimidazole class |
| GB26687/49A GB659479A (en) | 1948-11-09 | 1949-10-18 | Photographic emulsions containing yellow diffusion fast color formers of the benzimidazole class |
| DEG186A DE900781C (de) | 1948-11-09 | 1949-10-28 | Diffusionsfeste Gelbfarbbildner der Benzimidazolklasse |
| US143833A US2547307A (en) | 1948-11-09 | 1950-02-11 | Yellow diffusion-fast color formers of the benzimidazole class |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59203A US2500487A (en) | 1948-11-09 | 1948-11-09 | Yellow diffusion-fast color formers of the benzimidazole class |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2500487A true US2500487A (en) | 1950-03-14 |
Family
ID=22021460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US59203A Expired - Lifetime US2500487A (en) | 1948-11-09 | 1948-11-09 | Yellow diffusion-fast color formers of the benzimidazole class |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2500487A (en]) |
| BE (1) | BE492063A (en]) |
| DE (1) | DE900781C (en]) |
| FR (1) | FR998985A (en]) |
| GB (1) | GB659479A (en]) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992920A (en) * | 1957-03-15 | 1961-07-18 | Gevaert Photo Prod Nv | Production of colored photographic images |
| US5338654A (en) * | 1992-05-11 | 1994-08-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US20050085519A1 (en) * | 2001-07-27 | 2005-04-21 | Rubin Lee L. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| US20090170921A1 (en) * | 2004-01-14 | 2009-07-02 | Marc Gerspacher | Benzimidazole derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7901398A (en) * | 1998-06-22 | 2000-01-10 | Carrier Corporation | Fan mounting assembly |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| US2373821A (en) * | 1940-10-19 | 1945-04-17 | Gen Aniline & Film Corp | Production of color photographic images |
-
0
- BE BE492063D patent/BE492063A/xx unknown
- FR FR998985D patent/FR998985A/fr not_active Expired
-
1948
- 1948-11-09 US US59203A patent/US2500487A/en not_active Expired - Lifetime
-
1949
- 1949-10-18 GB GB26687/49A patent/GB659479A/en not_active Expired
- 1949-10-28 DE DEG186A patent/DE900781C/de not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| US2373821A (en) * | 1940-10-19 | 1945-04-17 | Gen Aniline & Film Corp | Production of color photographic images |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992920A (en) * | 1957-03-15 | 1961-07-18 | Gevaert Photo Prod Nv | Production of colored photographic images |
| US5338654A (en) * | 1992-05-11 | 1994-08-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US20050085519A1 (en) * | 2001-07-27 | 2005-04-21 | Rubin Lee L. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| US8354397B2 (en) | 2001-07-27 | 2013-01-15 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| US8772275B2 (en) | 2001-07-27 | 2014-07-08 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| US20090170921A1 (en) * | 2004-01-14 | 2009-07-02 | Marc Gerspacher | Benzimidazole derivatives |
| US8030497B2 (en) * | 2004-01-14 | 2011-10-04 | Novartis Ag | Benzimidazole derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR998985A (en]) | 1952-01-24 |
| BE492063A (en]) | |
| GB659479A (en) | 1951-10-24 |
| DE900781C (de) | 1954-01-04 |
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