US2691589A - Photographic developer compositions - Google Patents
Photographic developer compositions Download PDFInfo
- Publication number
- US2691589A US2691589A US372168A US37216853A US2691589A US 2691589 A US2691589 A US 2691589A US 372168 A US372168 A US 372168A US 37216853 A US37216853 A US 37216853A US 2691589 A US2691589 A US 2691589A
- Authority
- US
- United States
- Prior art keywords
- pyrazolidone
- reductone
- developer
- compounds
- compositions
- 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
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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/30—Developers
-
- 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/264—Supplying of photographic processing chemicals; Preparation or packaging thereof
- G03C5/265—Supplying of photographic processing chemicals; Preparation or packaging thereof of powders, granulates, tablets
Definitions
- This invention relates to photographic developers and particularly to methods for accelerating the development rate of photographic developing agents.
- a class of silver halide developing agents has come under consideration which in themselves are very weak developing agents for silver halide emulsions even under the most favorable conditions for development.
- H-C C- Reductone OH OH p-Aminobenzoic acid reductone p-Amino salicylic acid reductone m-Amino salicylic acid reductone Sulfanilic acid reductone Reference may be made to Chem. Zeit. 75, 21 (1951), for reductone and its derivatives.
- acteristic of the ene-diol-pyrazolidone developer compositions is that the developers show little tendency for the formation of silver sludge or for the formation of dichroic stain on silver images.
- a further advantage is that since the ene-diol compounds are very efiective preservatives for the pyrazolidone developing agents and are highly soluble in water, it is possible to prepare concentrated developer compositions more readily than in the case where a less soluble preservative such as sodium sulfite is used.
- a further characteristic of the ene-diol-pyrazolidone developer compositions of the invention resides in the fact that the compositions behave as strong surface latent image developers as opposed to internal latent image developers, as long as they are free of silver halide solvents such as sodium sulfite. That is, developer compositions containing S-pyrazolidone compounds have been described in the literature but invariably they have been compounded so as to contain a silver halide solvent such as sodium sulfite as a preservative. In order to convert such a developer composition to a surface latent image developer, we have found it to be necessary to dispense with the silver halide solvent in the developer composition. However, as mentioned, the 3-pyrazolidone developers free of preservative are very unstable.
- the ene-diol compounds are incorporated into the 3-pyrazolidone developer compositions, the ene-diol compounds supply the required preservative effect and the surface latent image developer characteristics are maintained. Therefore, the fortuitous choice of 3-pyrazo1idone compounds to accelerate the development rate of the ene-diol compounds has resulted in the latter compounds exerting a complementary preservative effect as well as providing a stable S-pyrazolidone developer system Which has surface latent image development characteristics and shows no tendency for physical
- the developers of the invention are very useful in color development processes where a black andwhite negative developer is required. As a result of such use in color processes, clean highlights are obtained and the color developed images have increased saturation because of decreased physical development in the negative developer.
- the 3-pyrazolidone developer compositions of the invention containing the above ene-diol compounds can be readily converted to internal latent image developer compositions by merely adding a silver halide solvent such as sodium thiosulfate thereto.
- the resultant internal latent image developer composition by virtue of the presence of one of the mentioned ene-diol compounds, likewise possesses excellent keeping properties even in the absence of the usual sulfite preservative.
- the 3-pyrazolidone silver halide developing agents employed in the developer compositions together with the reductions have the general structure in which the R groups each represent various substituents such as hydrogen, alkyl or aryl groups, for example, R1 can be hydrogen or a group such as alkyl preferably containing from 1 to a carbon atoms, or an aryl group of the benzene or naphthalene series substituted or not, and R2, R3, R4, and R can be hydrogen atoms or alkyl preferabl of l to 4 carbon atoms or aryl such as phenyl.
- R1 can be hydrogen or a group such as alkyl preferably containing from 1 to a carbon atoms, or an aryl group of the benzene or naphthalene series substituted or not
- R2, R3, R4, and R can be hydrogen atoms or alkyl preferabl of l to 4 carbon atoms or aryl such as phenyl.
- w-hydroXyaIkyI-S- pyrazolidones for example, compounds 18 and 24 above, are also especially useful in concentrated formulas, in replenishers, and in the presence of high salt concentrations where their increased solubility enables obtaining and holding adequate amounts of the pyrazolidone compound in solution.
- the compounds are described and claimed in the Allen et al. U. S. patent application Serial No. 372,148 filed concurrently herewith and in the Reynolds and Tinker U. S. patent application Seria1 No. 372,167 filed concurrently.
- the ene-diol compound reductone prepared from glucose by the method of Euler and Martius, Ann. 505, 73-87 (1933) and also obtained from sugars such as galactose, fructose, pentose, lactose, l-arabinose and levulose by treatment with hot alkali, is a reducing sugar especially valuable for use in the developer compositions of our invention since the development rate of the developers containing the compound is appreciably increased by the presence of the B-pyrazolidone compounds as will be seen from consideration of the data of the following examples.
- Example 1 A solution of reductone was obtained from 2 grams of glucose by heating the latter with 2 grams of sodium carbonate in 20 cc. of Water at 200 to 210 F. for 16 minutes. cc. of a buffer solution containing 0.1 molar sodium sesquicarbonate and 0.2 molar sodium sulfite was added and the resultant solution adjusted to pH 10.0 with alkali. To 50 cc. of the resulting solution was then added 0.04 gram of l-phenyl-B-pyrazolidone. The resultant developer was found to be very active, full development of an exposed film to a density of 2.0 being obtained in 5 minutes development at 68 F.
- Reductone prepared by the method of Euler The quantities of the ingredients in the developer compositions A, B and C are given in terms of moles per liter of solution. Each developer solution was adjusted to pH 10 with acetic acid before use in development of a fine-grain positive film for 4 minutes at 68 F. As a result, developer A developed weakly, producing density 0.42 and Example 2 A developer composition was prepared which was free of sulfite so as to provide a surface latent image developer, by heating a solution of 2 grams of glucose in 20 cc. of 0.5 molar sodium hydroxide solution for 90 seconds at ZOO-210 F. 80 cc. of 0.1 molar sodium sesquicarbonate solution was then added.
- Example 3 Density Reductone fromg ggg Alone 3-pyrazo1i- (32 min.) done Glucose 1. 30 2. 26 Galactose 1. 30 2. 10 l-Amhimun O. 88 2. U Levulose l. 34 2. 34 Lactose 0. 90 2. 00
- a comparable developer containing only 1- phenyl-3-pyrazolidone as the developing agent was used as a comparison and found to develop the same emulsion to a density of only 0.93 in 8 minutes and 1.5 in 32 minutes.
- Example 2 illustrates a surface latent image developer containing the pyrazolidone and reductone developing agents.
- developer compositions containing or free of silver halide solvents, are prepared from a. mixture of at least one of the mentioned pyrazolidone compounds and at least one of the reductone compounds.
- Particularly valuable developer compositions in addition to those exemplified above are those containing reductone and either a l--tolyl-3-pyrazolidone such as l-p-tolyl- 4,4-dimethyl-3-pyrazolidone or a l-(p-hydroxyalkylphenyl)-4,4-dia1kyl-3-pyrazolidone, such as l- (p-p-hydroxyethylphenyl) -4,4-dimethyl-3 pyrazolidone, or a l-(p-hydroxyalkylphenyl)-3-pyrazolidone such as 1-(p-fl-hydroxyethylphenyl)- S-pyrazolidone.
- a photographic developer composition comprising an alkaline material, a 3-pyrazolidone silver halide developing agent and a compound of the group consisting of reductone, p-aminobenzoic acid reductone, m-salicylic acid reductone, p-salicylic acid reductone, and sulfanilic acid reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of a 3-pyrazolidone silver halide developing agent and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of l-pheny1-3-pyrazo1idone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of a l-tolyl-3-pyrazolidone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of 1-p-tolyl4,4-dimethyl-3-pyrazolidone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of lphenyll,4-dimethyl-3-pyrazolidone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of 1-(p-p-hydroxyethylphenyl)-3pyrazolidone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of 1-p-tolyl-3-pyrazolidone and reductone.
- a photographic developer composition comprising an aqueous alkaline solution containing a mixture of 1- (p-fl-hydroxyethylphenyl) 4,4-dimethyl-3-pyrazolidone and reductone.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US371948A US2751297A (en) | 1953-08-03 | 1953-08-03 | Photographic emulsion layer containing a 3-pyrazolidone |
BE530883D BE530883A (xx) | 1953-08-03 | 1953-08-03 | |
US372166A US2688548A (en) | 1953-08-03 | 1953-08-03 | Photographic developer composition |
US372168A US2691589A (en) | 1953-08-03 | 1953-08-03 | Photographic developer compositions |
FR1106813D FR1106813A (fr) | 1953-08-03 | 1954-08-02 | Nouveau produit photosensible |
FR1106144D FR1106144A (fr) | 1953-08-03 | 1954-08-02 | Nouveau révélateur photographique |
FR1109575D FR1109575A (fr) | 1953-08-03 | 1954-08-02 | Révélateur photographique de nouvelle composition |
BE530887D BE530887A (xx) | 1953-08-03 | 1954-08-03 | |
GB22505/54A GB767699A (en) | 1953-08-03 | 1954-08-03 | Improvements in photographic developer compositions |
GB22510/54A GB767704A (en) | 1953-08-03 | 1954-08-03 | Improvements in photographic emulsions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US371948A US2751297A (en) | 1953-08-03 | 1953-08-03 | Photographic emulsion layer containing a 3-pyrazolidone |
US372168A US2691589A (en) | 1953-08-03 | 1953-08-03 | Photographic developer compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US2691589A true US2691589A (en) | 1954-10-12 |
Family
ID=27005592
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US371948A Expired - Lifetime US2751297A (en) | 1953-08-03 | 1953-08-03 | Photographic emulsion layer containing a 3-pyrazolidone |
US372166A Expired - Lifetime US2688548A (en) | 1953-08-03 | 1953-08-03 | Photographic developer composition |
US372168A Expired - Lifetime US2691589A (en) | 1953-08-03 | 1953-08-03 | Photographic developer compositions |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US371948A Expired - Lifetime US2751297A (en) | 1953-08-03 | 1953-08-03 | Photographic emulsion layer containing a 3-pyrazolidone |
US372166A Expired - Lifetime US2688548A (en) | 1953-08-03 | 1953-08-03 | Photographic developer composition |
Country Status (4)
Country | Link |
---|---|
US (3) | US2751297A (xx) |
BE (2) | BE530883A (xx) |
FR (3) | FR1109575A (xx) |
GB (2) | GB767704A (xx) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4154611A (en) * | 1978-02-27 | 1979-05-15 | Polaroid Corporation | Bicyclic reductone developing agents |
US4365085A (en) * | 1978-02-27 | 1982-12-21 | Polaroid Corporation | Bicyclic reductone developing agents |
US5273865A (en) * | 1990-04-24 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Photographic color developing composition and method for processing a silver halide color photographic element |
US5427905A (en) * | 1994-07-13 | 1995-06-27 | Polaroid Corporation | Thermally processable image-recording material including reductone developing agent |
EP0786698A1 (en) | 1996-01-23 | 1997-07-30 | Eastman Kodak Company | Organic/inorganic developer composition |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2875048A (en) * | 1957-09-30 | 1959-02-24 | Eastman Kodak Co | Combined photographic developing and stabilizing solution |
NL256771A (xx) * | 1960-10-12 | |||
US3278307A (en) * | 1961-11-21 | 1966-10-11 | Eastman Kodak Co | Photographic process for producing prints stabilized against print-out |
GB1054252A (xx) * | 1962-06-15 | |||
US3330661A (en) * | 1962-11-13 | 1967-07-11 | Eastman Kodak Co | Photographic development precursors |
US3300307A (en) * | 1963-01-18 | 1967-01-24 | Eastman Kodak Co | Photographic developer composition |
US3632340A (en) * | 1968-09-09 | 1972-01-04 | Eastman Kodak Co | Cored direct positive silver halide emulsion developed with polyhydroxybenzene |
US3649280A (en) * | 1968-11-29 | 1972-03-14 | Eastman Kodak Co | Photographic elements and compositions |
US4038080A (en) * | 1972-09-21 | 1977-07-26 | Minnesota Mining And Manufacturing Company | Fix and bleach-fix bath desilvering |
US3942985A (en) * | 1973-08-24 | 1976-03-09 | Minnesota Mining And Manufacturing Company | High contrast, rapid access, air stable, regenerable iron chelate developer solutions |
JPS6187148A (ja) * | 1984-10-05 | 1986-05-02 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
CA1267557A (en) | 1985-05-16 | 1990-04-10 | Shigeharu Koboshi | Method for color-developing a silver halide photographic light-sensitive material |
JPH03215845A (ja) | 1990-01-19 | 1991-09-20 | Fuji Photo Film Co Ltd | 直接ポジ写真感光材料 |
EP0449340B1 (en) * | 1990-02-26 | 1996-10-16 | Agfa-Gevaert N.V. | Photographic stabilizers containing a developer group |
JP2873852B2 (ja) | 1990-03-03 | 1999-03-24 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
US5147767A (en) * | 1991-04-10 | 1992-09-15 | Knapp Audenried W | Gluconic acid-based developer composition |
DE69223192T2 (de) * | 1991-08-16 | 1998-06-18 | Agfa Gevaert Nv | Ein photographisches Silberhalogenidmaterial |
EP0528480B1 (en) * | 1991-08-16 | 1997-11-19 | Agfa-Gevaert N.V. | A photographic silver halide material |
US5384232A (en) * | 1991-12-02 | 1995-01-24 | E. I. Du Pont De Nemours And Company | Process for rapid access development of silver halide films using pyridinium as development accelerators |
US5264323A (en) * | 1992-04-10 | 1993-11-23 | Eastman Kodak Company | Photographic developing solution and use thereof in the high contrast development of nucleated photographic elements |
US5236816A (en) * | 1992-04-10 | 1993-08-17 | Eastman Kodak Company | Photographic developing solution and use thereof in the high contrast development of nucleated photographic elements |
US5384233A (en) * | 1992-06-15 | 1995-01-24 | Konica Corporation | Chemicals kit including a container formed of multilayer film, for processing photographic light-sensitive materials |
JP3078431B2 (ja) * | 1993-09-27 | 2000-08-21 | 富士写真フイルム株式会社 | 黒白ハロゲン化銀写真感光材料の現像方法 |
US5399457A (en) * | 1993-10-15 | 1995-03-21 | Minnesota Mining And Manufacturing Company | Process for reducing sludge in diffusion transfer printing plates |
US5824458A (en) * | 1994-02-28 | 1998-10-20 | Fuji Photo Film Co., Ltd. | Developer and fixing solution for silver halide photographic material and processing method using the same |
US5798204A (en) * | 1994-07-26 | 1998-08-25 | Fuji Photo Film Co., Ltd. | Development processing method of ultrahigh-contrast black-and-white silver halide photographic material |
EP0704756B1 (en) * | 1994-09-09 | 2000-03-22 | Konica Corporation | Photographic processing method for processing a silver halide photographic light-sensitive material |
US5648205A (en) * | 1994-10-13 | 1997-07-15 | Fuji Photo Film Co., Ltd. | Processing method for silver halide photographic material |
JP3508081B2 (ja) * | 1995-10-30 | 2004-03-22 | コニカミノルタホールディングス株式会社 | ハロゲン化銀写真感光材料用固体処理剤および処理方法 |
JP3574986B2 (ja) * | 1996-01-16 | 2004-10-06 | コニカミノルタホールディングス株式会社 | ハロゲン化銀写真感光材料用固体処理剤及びハロゲン化銀写真感光材料の処理方法 |
EP0848287A1 (en) | 1996-12-11 | 1998-06-17 | Imation Corp. | Photographic silver halide developer composition and process for forming photographic silver images |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US742405A (en) * | 1901-12-17 | 1903-10-27 | Farbenfabriken Elberfeld Co | Photographic plate and process of making same. |
US2477462A (en) * | 1946-03-26 | 1949-07-26 | Du Pont | Polymeric color formers from hydroxyl polymers containing reactive ketaldone groups with reactive methylene and amino color formers |
US2672416A (en) * | 1949-11-16 | 1954-03-16 | Austin N Stanton | Reflex photography utilizing a luminescent light source |
GB679677A (en) * | 1950-04-06 | 1952-09-24 | Ilford Ltd | Improvements in or relating to pyrazolidones |
GB679678A (en) * | 1950-04-06 | 1952-09-24 | Ilford Ltd | Improvements in or relating to the production of 3-amino pyrazolines |
-
1953
- 1953-08-03 BE BE530883D patent/BE530883A/xx unknown
- 1953-08-03 US US371948A patent/US2751297A/en not_active Expired - Lifetime
- 1953-08-03 US US372166A patent/US2688548A/en not_active Expired - Lifetime
- 1953-08-03 US US372168A patent/US2691589A/en not_active Expired - Lifetime
-
1954
- 1954-08-02 FR FR1109575D patent/FR1109575A/fr not_active Expired
- 1954-08-02 FR FR1106144D patent/FR1106144A/fr not_active Expired
- 1954-08-02 FR FR1106813D patent/FR1106813A/fr not_active Expired
- 1954-08-03 GB GB22510/54A patent/GB767704A/en not_active Expired
- 1954-08-03 GB GB22505/54A patent/GB767699A/en not_active Expired
- 1954-08-03 BE BE530887D patent/BE530887A/xx unknown
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4154611A (en) * | 1978-02-27 | 1979-05-15 | Polaroid Corporation | Bicyclic reductone developing agents |
US4365085A (en) * | 1978-02-27 | 1982-12-21 | Polaroid Corporation | Bicyclic reductone developing agents |
US5273865A (en) * | 1990-04-24 | 1993-12-28 | Minnesota Mining And Manufacturing Company | Photographic color developing composition and method for processing a silver halide color photographic element |
US5427905A (en) * | 1994-07-13 | 1995-06-27 | Polaroid Corporation | Thermally processable image-recording material including reductone developing agent |
EP0692732A1 (en) | 1994-07-13 | 1996-01-17 | Polaroid Corporation | Thermally processable image-recording material including reductone developing agent |
EP0786698A1 (en) | 1996-01-23 | 1997-07-30 | Eastman Kodak Company | Organic/inorganic developer composition |
Also Published As
Publication number | Publication date |
---|---|
GB767699A (en) | 1957-02-06 |
GB767704A (en) | 1957-02-06 |
BE530887A (xx) | 1957-10-25 |
BE530883A (xx) | 1957-10-25 |
FR1106813A (fr) | 1955-12-23 |
US2688548A (en) | 1954-09-07 |
FR1109575A (fr) | 1956-01-31 |
FR1106144A (fr) | 1955-12-12 |
US2751297A (en) | 1956-06-19 |
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