US2522802A - Production of yellow dye images by color development - Google Patents
Production of yellow dye images by color development Download PDFInfo
- Publication number
- US2522802A US2522802A US66825A US6682548A US2522802A US 2522802 A US2522802 A US 2522802A US 66825 A US66825 A US 66825A US 6682548 A US6682548 A US 6682548A US 2522802 A US2522802 A US 2522802A
- Authority
- US
- United States
- Prior art keywords
- acid
- emulsion
- color
- image
- yellow dye
- 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
- 239000001043 yellow dye Substances 0.000 title description 11
- 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 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 SILVER HALIDE Chemical class 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 239000000839 emulsion Substances 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 13
- 229910052709 silver Inorganic materials 0.000 claims description 13
- 239000004332 silver Substances 0.000 claims description 13
- 238000004061 bleaching Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 150000001721 carbon Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000003254 radicals Chemical class 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
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ONYVFNRTXGLOKY-UHFFFAOYSA-N 3-oxo-3-phenyl-n-(4-sulfamoylphenyl)propanamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC(=O)CC(=O)C1=CC=CC=C1 ONYVFNRTXGLOKY-UHFFFAOYSA-N 0.000 description 1
- WOQBMUQZUJEXTD-UHFFFAOYSA-N 4-[(3-oxo-3-phenylpropanoyl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)CC(=O)C1=CC=CC=C1 WOQBMUQZUJEXTD-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- 229930194542 Keto Natural products 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
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000004171 alkoxy aryl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 125000005026 carboxyaryl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[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
- G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
Definitions
- Patented Sept. 19, 1950 PRODUCTION OF YELLOW DYEIMAGESBY.
- the present invention relates; to the preparation of yellow dye images by photographic color forming development.
- a permanent'yel'low dye image can be produced simultaneously with the cyan and maenta azine dye images by color forming development with a 2.4-diamirxo aniline in the presence of a keto methylene compound providing that the pH of the photographic element subaniline in the presence of a colon former which is preferably an aromatic compound containing at least one hydroxyl, group linked to the aromatic structure.
- a colon former which is preferably an aromatic compound containing at least one hydroxyl, group linked to the aromatic structure.
- hydroxy alkyll- such as hydroxy ethyl
- sulfo alkyl such as sulfomethyl, sulfopropyl, sulfobutyl and the like, or an aromatic radical such as aryl, i. e., phenyl, naphthyl and the like, carboxy aryl, i. e., carboxy phenyl, carboxy naphthyl and the like, sulfo aryl, i.
- alkoxy aryl such as methoxy phenyl, methoxy naphthyl, ethoxy phenyl, butyroxy phenyl and the like, alkyl aryl such as toluyl, ethylphenyl, propylphenyl and the like, carboxy alkylaryl, such as carboxy methyl phenyl, carboxy' ethyl phenyl and the like, carboxy alkoxy aryl, such as carboxy methoxy phenyl, carboxy ethoxy phenyl, hydroxy alkyl aryl such as hydroxy methyl phenyl, hydroxy ethyl phenyl and the like, and hydroxy a1- koxy aryl such as hydroxy methoxy phenyl, hydroxy ethoxy phenyl and the like, R is an aromatic or aliphatic
- the color former which is utilized for the for- H2 mation of the yellow dye image upon development is any open chain keto methylene compound, i. e., any compound containing in a straight chain a methylene group which is activated by one or more keto groups or by a keto group and a cyano or SO2 group.
- the benzimidazole compounds 1. e., Nos. 13 and 32, are new products. Such compounds are produced, taking compound 32, for example, by
- keto methylene compounds are well known, and are used, for example, as
- Compound 13 is made .in the same manner excepting that 2--(4' -,aminophenyl)--l-octadecylbenzimidazole--sulfonic acid is replaced by .2- .(3' aminophenyl) -1-octadecylbenzimidazole 5- :sulfonic acid. 1
- the parent benzimidazole is prepared byheating a 3-amino-4-alkylamino benzene sulfonic or :carboxylic acid with the -de- ⁇ sired nitro benzenecarboxylic acid chloride in the presence ,of pyridine or any .other suitable :acid binding agent.
- the .nitro group in the benbimidazole is then reduced 'to an amino group.
- Preparation of the intermediate is analogous to 'the :method described iin .copending application Serial (No. 745,113, filed April 30, 1947, with :the "exception that the l -hydroxy-2enaphthoylchloride is replaced by the desired nitro-benzoyl chloride followed by reduction of thenitro group after ring closure.
- the alkali treatment step leading toyellowrdye image formation is conducted before final "washing and drying and involves merely the subjection of the photographic element being processed to the action of @an aqueous solution of a. water rsoluble alkali, such as sodium carbonate, potassium carbonate and the like. As the pH of the photographic elementincreases, the yellow image appears as a result roftthe transformation of the previously formed magenta image.
- the particular stage at which the alkali treatment is interposed may varydepending upon the nature of the fixing bath employed. Generally speaking, such alkali treatment will be a final phase of the processing operation and will usually lbelsucceeded by the final wash and drying. This order will always prevail 'where the fixing bath is acidic. If, however, the fixing bath is neutral, then the alkali treatment may follow bleaching and precede fixing. In any case, the
- the process may be carriedrout by utilizing the color formers in the color forming developer or in the silver-halide emulsion.
- the color formers are'loca'ted in the emulsion and are so constituted that they do not difluse therefrom .during the photographic processing.
- the color formers may be rendered fast to ,dif- ,insion in the emulsions by methods usually employedin the art, for example, those described in Unitedv States Patents Nos.
- the process may be utilized for the formation "0;? ,negative :color images, positive color images,
- the yellow dye images produced by the present invention have excellent light fastness and brilliance and very adequately complement the magenta and cyan dyes produced by the azine process.
- Example 1 To 100 ml. of a developer solution made up as follows:
- Example 2 A photographic silver halide emulsion containing as a non-difiusing color former p-cyanoacetyl-B-octadecenyl-succinalic acid having the following constitution:
- Example 3 The procedure is the same as in Example 1 excepting that the developer is made up of equal parts of 4.6-di-(phenylamino)-metanilic acid silver halide emulsion in the presence of an open chain keto methylene compound with a 2.4-diamino-aniline in which the nitrogen atoms in 2- and 4-positions have directly linked thereto a carbon atom of a radical selected from the class consisting of aliphatic and aromatic radicals, bleaching and fixing said emulsion, and adjusting the pH of the emulsion in a final phase of the processing operation by treatment with an alkali untilthe yellow image manifests itself when the emulsion has been previously subjected to an acidic treating bath.
- a radical selected from the class consisting of aliphatic and aromatic radicals
- the process of producing yellow dye images which are resistant to splitting by strong mineral acids which comprises developing a devolopable silver halide emulsion in the presence of an open chain keto methylene compound with a 2.4-diamino-aniline in which the nitrogen atoms in 2- and 4-positions are directly linked to the carbon atom of a radical selected from the class consisting of aliphatic and aromatic radicals, bleaching the silver formed by such development, fixing the silver salts by an acid hardening fixing bath, and subsequently adjusting the pH of the emulsion by treatment with an alkali until the yellow image manifests itself.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE492847D BE492847A (cs) | 1948-12-22 | ||
| US66825A US2522802A (en) | 1948-12-22 | 1948-12-22 | Production of yellow dye images by color development |
| GB31880/49A GB662419A (en) | 1948-12-22 | 1949-12-12 | Production of yellow dye photographic images by color development |
| DEG607A DE827901C (de) | 1948-12-22 | 1949-12-16 | Verfahren zur Herstellung von gelben Farbstoffbildern durch farbbildende Entwicklung |
| FR1003992D FR1003992A (fr) | 1948-12-22 | 1949-12-20 | Procédé de production d'images de colorant jaune pour développement en couleurs |
| CH289721D CH289721A (fr) | 1948-12-22 | 1949-12-22 | Procédé de production d'images de colorant jaune par développement photographique chromogène. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66825A US2522802A (en) | 1948-12-22 | 1948-12-22 | Production of yellow dye images by color development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2522802A true US2522802A (en) | 1950-09-19 |
Family
ID=22071952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US66825A Expired - Lifetime US2522802A (en) | 1948-12-22 | 1948-12-22 | Production of yellow dye images by color development |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2522802A (cs) |
| BE (1) | BE492847A (cs) |
| CH (1) | CH289721A (cs) |
| DE (1) | DE827901C (cs) |
| FR (1) | FR1003992A (cs) |
| GB (1) | GB662419A (cs) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3099559A (en) * | 1959-08-31 | 1963-07-30 | Gen Aniline & Film Corp | Silver-free color reproduction process and composition therefor |
| US3178286A (en) * | 1959-11-05 | 1965-04-13 | Gevaert Photo Prod Nv | Light sensitive photographic color element |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
-
0
- BE BE492847D patent/BE492847A/xx unknown
-
1948
- 1948-12-22 US US66825A patent/US2522802A/en not_active Expired - Lifetime
-
1949
- 1949-12-12 GB GB31880/49A patent/GB662419A/en not_active Expired
- 1949-12-16 DE DEG607A patent/DE827901C/de not_active Expired
- 1949-12-20 FR FR1003992D patent/FR1003992A/fr not_active Expired
- 1949-12-22 CH CH289721D patent/CH289721A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2414491A (en) * | 1945-01-27 | 1947-01-21 | Gen Aniline & Film Corp | Photographic developer |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3099559A (en) * | 1959-08-31 | 1963-07-30 | Gen Aniline & Film Corp | Silver-free color reproduction process and composition therefor |
| US3178286A (en) * | 1959-11-05 | 1965-04-13 | Gevaert Photo Prod Nv | Light sensitive photographic color element |
| US4066457A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Color developer for diffusion transfer |
| US4066456A (en) * | 1974-12-10 | 1978-01-03 | Gaf Corporation | Incorporated carboxy substituted p-phenylenediamine color developer |
Also Published As
| Publication number | Publication date |
|---|---|
| GB662419A (en) | 1951-12-05 |
| FR1003992A (fr) | 1952-03-24 |
| CH289721A (fr) | 1953-03-31 |
| BE492847A (cs) | |
| DE827901C (de) | 1952-03-17 |
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