US3394004A - Photographic material for the silver dyestuff bleaching process - Google Patents
Photographic material for the silver dyestuff bleaching process Download PDFInfo
- Publication number
- US3394004A US3394004A US440303A US44030365A US3394004A US 3394004 A US3394004 A US 3394004A US 440303 A US440303 A US 440303A US 44030365 A US44030365 A US 44030365A US 3394004 A US3394004 A US 3394004A
- Authority
- US
- United States
- Prior art keywords
- bleaching
- silver
- dyestuff
- pyrazine
- bath
- 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
- 238000004061 bleaching Methods 0.000 title description 78
- 239000000975 dye Substances 0.000 title description 42
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title description 40
- 229910052709 silver Inorganic materials 0.000 title description 39
- 239000004332 silver Substances 0.000 title description 39
- 238000000034 method Methods 0.000 title description 27
- 230000008569 process Effects 0.000 title description 19
- 239000000463 material Substances 0.000 title description 12
- 239000003054 catalyst Substances 0.000 description 40
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 33
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 18
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
- 150000003216 pyrazines Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- -1 for example Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 description 2
- AJIRUIWLEVHQMU-UHFFFAOYSA-N 3-aminophenazin-2-ol Chemical compound C1=CC=C2N=C(C=C(C(N)=C3)O)C3=NC2=C1 AJIRUIWLEVHQMU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- IYQHCPGJNZBANF-UHFFFAOYSA-N phenazine-1,2-diamine Chemical compound C1=CC=CC2=NC3=C(N)C(N)=CC=C3N=C21 IYQHCPGJNZBANF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- GZXXANJCCWGCSV-UHFFFAOYSA-N 2,3-Diethylpyrazine Chemical class CCC1=NC=CN=C1CC GZXXANJCCWGCSV-UHFFFAOYSA-N 0.000 description 1
- HPHATBFPSZWBQQ-UHFFFAOYSA-N 2,3-dimethylquinoxalin-5-amine Chemical compound C1=CC(N)=C2N=C(C)C(C)=NC2=C1 HPHATBFPSZWBQQ-UHFFFAOYSA-N 0.000 description 1
- FKHNZQFCDGOQGV-UHFFFAOYSA-N 2,3-dimethylquinoxaline Chemical compound C1=CC=C2N=C(C)C(C)=NC2=C1 FKHNZQFCDGOQGV-UHFFFAOYSA-N 0.000 description 1
- NDRRHMFFDGQFLE-UHFFFAOYSA-N 2-aminophenazin-1-ol Chemical compound C1=CC=CC2=NC3=C(O)C(N)=CC=C3N=C21 NDRRHMFFDGQFLE-UHFFFAOYSA-N 0.000 description 1
- ZFTPKCMLINOUTC-UHFFFAOYSA-N 3-aminophenazin-2-ol hydrochloride Chemical compound NC1=CC2=NC3=CC=CC=C3N=C2C=C1O.Cl ZFTPKCMLINOUTC-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- CMCWWLVWPDLCRM-UHFFFAOYSA-N phenidone Chemical compound N1C(=O)CCN1C1=CC=CC=C1 CMCWWLVWPDLCRM-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ZUCRGHABDDWQPY-UHFFFAOYSA-N pyrazine-2,3-dicarboxylic acid Chemical class OC(=O)C1=NC=CN=C1C(O)=O ZUCRGHABDDWQPY-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003918 triazines Chemical class 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
- G03C7/28—Silver dye bleach processes; Materials therefor; Preparing or processing such materials
Definitions
- ABSTRACT OF THE DISCLOSURE A process for the production of colored photographic images by the silver dyestuff bleaching process, wherein bleaching is carried out in a dyestuff bleaching bath containing a pyrazine as bleaching catalyst or a pyrazine is added to a bath preceding the dyestuff bleaching bath or wherein photographic material is used that contains at least one layer containing a pyrazine as bleaching catalyst.
- the present invention relates to dyestuff bleaching catalysts for the silver dyestuff bleaching process.
- the production of colored photographic images by the silver dyestuff bleaching process is based on the principle that organic dyestuffs, especially azo dyestuffs, are destroyed by metallic silver in suitable baths.
- these baths contain a mineral acid, for example, hydrochloric acid, or a strong organic carboxylic acid, potassium bromide and a compound capable of forming silver complexes, for example, thiourea.
- a mineral acid for example, hydrochloric acid
- a strong organic carboxylic acid, potassium bromide a compound capable of forming silver complexes, for example, thiourea.
- 4 silver atoms reduce one azo group with formation of colorless amines.
- azo dyestuffs differ greatly from one another in respect of their behaviour in this reduction process, the differences being mainly in the time required to bring about reduction to a colorless substance.
- the silver dyestuff bleaching process is generally not carried out to its conclusion with utilization of the total amount of metallic silver present, but is tenninated after a certain period after only a proportion of the said silver has been consumed.
- bleaching continues at those areas where metallic silver is still present, which means that there may be a paucity of halftones, particularly at areas of low color density.
- a catalyst is required in the bleaching of some azo dyestuffs in order to equal out a large extent the bleaching times for the different dyestuffs and, Where necessary to permit bleaching to a pure white.
- Compounds that have been proposed as bleaching catalysts, and some of which have been used successfully are, for example, 2:3 dimethylquinoxaline, 2:3 diaminophenazine, 2-hydroxy-3-aminophenazine and anthraquinone sulphonic acid.
- the catalysts are added to the silver dyestuff bleaching bath in the usual manner, or are incorporated in the photographic color layer. It is also known to add the catalysts to a bath preceding the silver dyestuff bleaching bath.
- catalysts and methods of using them available. Nevertheless, the use of catalysts is frequently beset with difficulties. In particular, it is difficult to catalyse the bleaching process in a manner such that the different dyestuffs present in multilayer material are properly attuned to one another as regards bleaching. For example, a particular catalyst can shorten the bleaching time of the yellow and cyan dyestuffs but have no influence on the bleaching time of the magenta dyestuff. Conversely, the magenta dyestuff can respond well to a catalyst and the yellow and cyan dyestuffs remain unaffected.
- a further disadvantage associated with the bleaching caralysts known hitherto is that the compounds that are effective in low concentrations of about 1 to 10 milligrams per liter as, for example, 2:3 diaminophenazine and 2- hydroxy-3-aminophenazine, have a very pronounced color of their own. This can result in undesirable coloration of the gelatine or support.
- the known uncolored catalysts for example, 2:3-dimethylquinoxaline, have a much weaker action and thus have to to used in larger amounts.
- disazo dyestuffs especially cyan disazo or azoxyazo dyestuffs
- the well-known symmetrical disazo dyestuff obtained from tetrazotized 3:3- dirnethoxy 4:4 diaminodiphenyl and 1 amino-S-hydroxynaphthalene-Z:4-disulphonic acid
- bleaching with the known catalysts proceeds in a manner such that only the first azo group is split up and a violet monoazo dyestuff is left in the layers. It is therefore desirable to have catalysts that catalyse the splitting'of the monoazo dyestuff that is produced; the said dyestuff is particularly noticeable and undesirable at the white areas of the image.
- the present invention is based on the observation that specially good results are obtained when pyrazines are used as bleaching catalysts in the silver dyestuff bleaching process.
- the present invention therefore provides a process for the production of colored photographic images by the silver dyestuff bleaching process, wherein bleaching is carried out in a dyestuff bleaching bath containing a pyrazine as bleaching catalyst or a pyrazine is added to a bath preceding the dyestuff bleaching bath or wherein photographic material is used that contains at least one layer containing a pyrazine as bleaching catalyst.
- the pyrazines possess surprisingly advantageous properties compared with the known dyestuff bleaching catalysts.
- they are colorless and are effective when used in very low concentrations, and they also catalyse the second reaction step in the case of many known cyan dyestuffs; in other Words, they ensure bleaching of the monoazo dyestuff to colorless cleavage products.
- pyrazines refers solely to compounds containing at least one ring of the formula which is not condensed with other rings, which ring may also be depicted in a simplified manner as follows:
- the pyrazine ring may carry substituents, for example, this catalyst is capable of promoting the complete bleachcarboxylic acid groups or alkyl groups, for example, ethyl ing of all dyestuffs. When used in higher concentrations groups or especially methyl groups. For example, catalysts it also acts on layers that do not contain silver and is can be used that correspond to the formula thus the cause of so-called bleach-coupling. (3) N 5 The last-mentioned property is much less pronounced in the case of the substitution products of pyrazine, and EFF -Rz the latter have therefore been found to be especially ⁇ N valuable because of their specific action on certain dyestuffs.
- the photographlc mateflal d pyrazines of the kind d fi d can be derived f example, tains three colored layers on a support of cellulose acetate from 2-amino-3:6-dimethylpyrazine on the one hand and film, and 1S bill p as fOH'OWSI from a monocarboxylic add f example, benzoic acid,
- the said pyrazines can COH1 I H (?CH3 Ht) be added to the photographic color layer, to an intermediate layer, to the dyestufi" bleaching bath or to a bath preceding the dyestuff bleaching bath, for example, to the developer, a hardening bath, a stop bath or a special bath H035 "303E l) following the fixing bath. Furthermore, it can also be ad- 40 vantageous to use the pyrazines in conjunction with dye- Hots stuff bleaching catalysts having a different constitution, Second layer: A gelatine intermediate layer. for example, with quinoxalines or phenazines. For ex- Third layer: A green-sensitized silver bromide emulsion ample, the pyrazines can be used as catalysts in combinacontaining a magenta dyestuff of the formula.
- a gelatine intermediate layer aminohydroxyphenazine.
- a layer containing a yellow filter dye- Unsubstituted pyrazine is a colorless compound which stuff or colloidal silver acting as yellow filter.
- halogenated triazine zine per liter of bleaching bath comprising to parts compound, for example, with 2:4-dichloro-6-phenylof hydrochloric acid of 30% strength, 100 to parts amino-1:3:5-triazine-3-sulfonic acid.
- the material is washed in water for a short time, and then bleached in a silver dyestuff bleaching bath containing, per liter of water, 30 grams of thiourea, grams of potassium bromide, 70 ml. of hydrochloric acid of 30% strength and 3 ml. of a 1% solution of 2:5-dimethylpyrazine in water.
- the bleaching time is 8 to 15 minutes.
- the material is given a short wash with water and then the residual metallic silver is converted into silver halide in the usual manner in a bath containing copper sulphate, hydrochloric acid and potassium bromide.
- the material is then washed with water, fixed with a 10% solution of ammonium thiosulfate and again washed.
- the aminodimethylquinoxaline in the developer can be replaced 'by 2:5-dimethylpyrazine in amounts of 0.005 to 0.01 gram per liter of developer or by 2-amino-3-hydroxyphenazine hydrochloride.
- casting material contains 160 to 230 grams of gelatine (depending on the degree of viscosity required) and also 145 to 500 ml. of an aqueous or alkaline solution of 1.5 grams of the catalyst, for example, pyrazine-2:3-dicarboxylic acid or 2-benzoylamino-3z6-dimethylpyrazine.
- the catalyst for example, pyrazine-2:3-dicarboxylic acid or 2-benzoylamino-3z6-dimethylpyrazine.
- the incorporated catalysts diffuse into the dyestutf layer and promote uni form bleaching of the dyestuffs.
- EXAMPLE 3 Material having the composition indicated in Example 1 is treated in the manner described in Example 1. However, instead of 3 ml. of a 1% aqueous solution of dimethylpyrazine, 10 to ml. of a 0.2% solution of one of the following pyrazine compounds in methanol are added to the bleaching bath:
- the improvement which comprises carrying out the silver dyestuif bleaching operation in the presence of the pyrazine of the formula HaC N .as a dyestuif bleaching catalyst.
- the improvement which comprises carrying out the silver dyestulr' bleaching operation in the presence of the pyrazine of the formula as a dyestuff bleaching catalyst.
- the improvement which comprises carrying out the silver dyestutf bleaching operation in the presence of the pyrazine of the formula N Wl-c 0 on COO1I as a dyestuif bleaching catalyst.
- the improvement which comprises canying out the silver dyestuff bleaching operation in the presence of the pyrazine of the formula as a dyestuif bleaching catalyst.
- a silver dyestuff bleaching bath containing in Vitus thiourea, potassium bromide, a strong acid and a pyrazine of the formula in which R and R each represents a member selected from the group consisting of a hydrogen atom, a methyl group and a carboxylic acid group as a dyestufi bleaching catalyst.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH361864A CH438936A (de) | 1964-03-20 | 1964-03-20 | Verwendung von Pyrazinen als Farbbleichkatalysatoren im Silberfarbbleichverfahren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3394004A true US3394004A (en) | 1968-07-23 |
Family
ID=4259842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US440303A Expired - Lifetime US3394004A (en) | 1964-03-20 | 1965-03-16 | Photographic material for the silver dyestuff bleaching process |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3394004A (en:Method) |
| AT (1) | AT257358B (en:Method) |
| BE (1) | BE661358A (en:Method) |
| CH (1) | CH438936A (en:Method) |
| DE (1) | DE1269483B (en:Method) |
| ES (1) | ES310746A1 (en:Method) |
| GB (1) | GB1051970A (en:Method) |
| NL (1) | NL6503517A (en:Method) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868253A (en) * | 1972-02-28 | 1975-02-25 | Ciba Geigy Ag | Process for the rapid processing of silver dye bleach material |
| US4271254A (en) * | 1977-10-28 | 1981-06-02 | Ciba-Geigy Ag | Process for producing photographic images |
| US4304846A (en) * | 1979-02-09 | 1981-12-08 | Ciba-Geigy Ag | Method for processing silver dye-bleach materials |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH543108A (de) * | 1970-09-04 | 1973-10-15 | Ciba Geigy Ag | Verwendung von Chinoxalinen in photographischen Verfahren |
| ATE164238T1 (de) * | 1991-06-11 | 1998-04-15 | Jahleel Corp | Bleichbad und seine verwendung in einem silberfarbbleichverfahren |
| US5550009A (en) * | 1995-04-17 | 1996-08-27 | Eastman Kodak Company | Stabilized peroxide bleaching solutions and their use for processing of photographic elements |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2270118A (en) * | 1936-12-14 | 1942-01-13 | Chromogen Inc | Production of colored photographic pictures |
| US3156561A (en) * | 1958-06-03 | 1964-11-10 | Ciba Geigy Corp | Method of producing color photographic pictures |
-
0
- GB GB1051970D patent/GB1051970A/en active Active
-
1964
- 1964-03-20 CH CH361864A patent/CH438936A/de unknown
-
1965
- 1965-03-10 ES ES0310746A patent/ES310746A1/es not_active Expired
- 1965-03-16 US US440303A patent/US3394004A/en not_active Expired - Lifetime
- 1965-03-19 DE DEP1269A patent/DE1269483B/de active Pending
- 1965-03-19 AT AT251865A patent/AT257358B/de active
- 1965-03-19 BE BE661358A patent/BE661358A/xx unknown
- 1965-03-19 NL NL6503517A patent/NL6503517A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2270118A (en) * | 1936-12-14 | 1942-01-13 | Chromogen Inc | Production of colored photographic pictures |
| US3156561A (en) * | 1958-06-03 | 1964-11-10 | Ciba Geigy Corp | Method of producing color photographic pictures |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868253A (en) * | 1972-02-28 | 1975-02-25 | Ciba Geigy Ag | Process for the rapid processing of silver dye bleach material |
| US4271254A (en) * | 1977-10-28 | 1981-06-02 | Ciba-Geigy Ag | Process for producing photographic images |
| US4304846A (en) * | 1979-02-09 | 1981-12-08 | Ciba-Geigy Ag | Method for processing silver dye-bleach materials |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1051970A (en:Method) | |
| AT257358B (de) | 1967-10-10 |
| BE661358A (en:Method) | 1965-09-20 |
| CH438936A (de) | 1967-06-30 |
| DE1269483B (de) | 1968-05-30 |
| NL6503517A (en:Method) | 1965-09-21 |
| ES310746A1 (es) | 1966-01-01 |
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