US3140178A - Photographic silver halide emulsions containing thioether derivatives as antifoggants and stabilizers - Google Patents
Photographic silver halide emulsions containing thioether derivatives as antifoggants and stabilizers Download PDFInfo
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- US3140178A US3140178A US133768A US13376861A US3140178A US 3140178 A US3140178 A US 3140178A US 133768 A US133768 A US 133768A US 13376861 A US13376861 A US 13376861A US 3140178 A US3140178 A US 3140178A
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- silver halide
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- addenda
- emulsions
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- 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
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- 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
- 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
- G03C1/43—Processing agents or their precursors, not covered by groups G03C1/07 - G03C1/42
Definitions
- This invention relates to photographic compositions.
- Preferred embodiments of the invention concern photographic silver halide emulsions containing certain mercapto derivatives that can serve as fog-inhibiting agents or as stabliizing agents obviating the necessity of conventional fixing.
- photographic silver halide emulsions having incorporated therein sulfur-containing derivatives having either the formula can be represented by the formula 3,140,178 Patented July 7, 1964 wherein Y is a hydrogen atom, a nitro radical, an alkoxy radical (OR), an acyl radical a tertiary amino radical and others, with R and R being alkyl radicals having 1 to 20 and preferably 1 to 4 carbon atoms.
- the thioether radical for the substituent X can be represented by the formula -SZ wherein Z represents an organic radical such as an aryl radical, an aralkyl radical, a substituted alkyl radical, a heterocyclic radical or the like. Typical thioether radicals include such radicals as:
- R is a carboxyl radical, an amino radical or an alkyl radical generally having 1 to 20 and preferably 1 to 4 carbon atoms;
- n is an integer of 1 to 10 and preferably 1 to 4 and wherein R is the same as described above;
- R is an alkylene radical having 1 to 20 and preferably 1 to 4 carbn atoms and M is an amide radical, a sulfonyl radical, a hydroxyl radical, an alkoxy radical, an amino radical, an ester radical, a carboxyl radical or a heterocyclic radical such as a morpholino radical; or a heterocyclic organic radical such as a phenyl tetrazine radical, a morpholino radical or the like.
- Illustrative alkyl radicals for the above substituents include methyl, ethyl, n-butyl, Z-ethylhexyl, n-decyl, n-dodecyl, stearyl, eicosyl etc. as well as analogous alkylene radicals for the alkylene substituents.
- the addenda having the structure of Formula A above are B-aminosulfides that can be readily prepared by reacting thiols and Schiif bases such as azamethines as described in Stacy et al., J.A.C.S., 77, 3869, 1955 and which can be represented by the following equation to prepare a typical thioether derivative addenda of the invention by reacting p-thiocresol and benzalaniline:
- the addenda having the structure of Formula B above are Michael adducts that can be readily prepared by reacting thiols and unsaturated compounds having an activating proton substituent as described in Tarbell and Harnish, Chem. Rev., 49, 23, 1951, and which can be represented by the following equation to prepare a typical thioether derivative or addenda of the invention by reacting mercapto pivalic acid and chalcone:
- the feature addenda of the invention can be utilized in photographic silver halide emulsions to serve as antifoggants. These addenda serve to stabilize emulsions under prolonged storage conditions or under conditions of high temperature and humidity which typically occur in tropical climates.
- the amount of the subject addenda that is used in photographic silver halide emulsions for antifoggant purposes can be varied in accordance with usual practice, the amount utilized varying with the effect desired, degree of ripening, silver content of the emulsion, etc. Generally from about .001 to grams of addenda per mole of silver halide are suitable for antifoggant purposes.
- the photographic silver halide emulsion addenda of the invention can also serve as incorporated fixing agents. These addenda do not prevent development of exposed areas of the emulsion but protect the unexposed areas of the emulsion against print out after development of the emulsion. Thus with emulsions containing the addenda of the invention, silver images can be formed and stabilized without the use of a conventional fixing process.
- the subject addenda are stable and do not act as fixing agents in acidic or neutral media such as in emulsions. However, under aqueous alkaline conditions, such as prevail during the developing of photographic emulsions, the subject addenda become active fixing agents.
- the preparation of photographic silver halide emulsions such as are used with the addenda of this invention involves three separate operations: (1) emulsification and digestion of silver halide, (2) the freeing of the emulsion of excess water-soluble salts, suitably by washing with water, and (3) the second digestion or afterripening to obtain increased emulsion speed or sensitivity.
- the addenda of the invention can be added to the emulsion before the final digestion or after-ripening, or they can be added immediately prior to the coating.
- the addenda of the invention can be added to photo graphic emulsions using any of the well-known techniques in emulsion making. For example, they can be dissolved in a suitable solvent and added to the silver halide emulsion, or they can be added to the emulsion in the form of a dispersion similar to the technique used to in corporate certain types of color-forming compounds (couplers) in a photographic emulsion. Techniques of this type are described in Jelley et al. U.S. Patent 2,322,- 027, issued June 15, 1943, and Fierke et al. U.S. Patent 2,801,171, issued July 30, 1957.
- the solvent should be selected so that it has no harmful effect upon the emulsion in accordance with usual practice, and generally solvents or diluents which are miscible with water are to be preferred.
- the emulsions of the invention can be chemically sensitized by any of the other well-known procedures.
- emulsions can be digested with naturally active gelatin, or sulfur compounds can be added, such as those described in Sheppard U.S. Patent 1,574,944, issued March 2, 1926, and Sheppard et al. 1,623,499, issued April 5, 1927, and Sheppard and Brigham U.S. Patent 2,410,689, issued November 5, 1946.
- the emulsions can also be treated with salts of the noble metals such as ruthenium, rhodium, palladium, iridium and platinum.
- Representative compounds are ammonium chloropalladate, potassium chloroplatinate, and sodium chloropalladite, which are used for sensitizing in amounts below that which produces any substantial fog inhibition, as described in Smith and Trivelli U.S.
- Patent 2,448,060 issued August 31, 1948, and as antifoggants in higher amounts, as described in Trivelli and Smith U.S. Patents 2,566,245, issued August 28, 1951, and 2,566,263, issued August 28, 1951.
- the emulsions can also contain sensitizing amounts of gold salts as described in Waller et al. U.S. Patent 2,399,- 083, issued April 23, 1946, or stabilizing amounts of gold salts as described in Damschroder U.S. Patent 2,597,- 856, issued May 27, 1952, and Yutzy and Leermakers U.S. Patent 2,597,915, issued May 27, 1952.
- Suitable compounds are potassium chloroaurite, potassium aurithiocyanate, potassium chloroaurate, auric trichloride and 2-aurosulfobenzothiazole methochloride.
- the emulsions can also contain sensitizing amounts of reducing agents such as stannous salts (Carroll U.S. Patent 2,487,850, issued November 15, 1949), polyamines, such as diethylene triamine (Lowe and Jones U.S. Patent 2,518,698, issued August 15, 1950), polyamines, such as spermine (Lowe and Allen U.S. Patent 2,521,925, issued September 12, 1950), or bis(B-aminoethyl)sulfide and its watersoluble salts (Lowe and Jones U.S. Patent 2,521,926, issued September 12, 1950).
- reducing agents such as stannous salts (Carroll U.S. Patent 2,487,850, issued November 15, 1949), polyamines, such as diethylene triamine (Lowe and Jones U.S. Patent 2,518,
- the emulsions can also be optically sensitized with cyanine and merocyanine dyes, such as those described in Brooker U.S. Patents 1,846,301, issued February 23, 1932; 1,846,302, issued February 23, 1932; and 1,942,- 854, issued January 9, 1934; White U.S. Patent 1,990,507, issued February 12, 1935; Brooker and White U.S. Patents 2,112,140, issued March 22, 1938; 2,165,338, issued July 11, 1939; 2,493,747 issued January 10, 1950; and 2,739,964, issued March 27, 1956; Brooker and Keyes U.S. Patent 2,493,748, issued January 10, 1950; Sprague U.S.
- the emulsions of the invention can also contain such stabilizing compounds as the mercury compounds of Allen, Byers, and Murray U.S. Patent 2,728,663, issued December 27, 1955; Carroll and Murray U.S. Patent 2,728,664, issued December 27, 1955; and Leubner and Murray U.S. Patent 2,728,665, issued December 27, 1955; the triazoles of Heimbach and Kelly U.S. Patent 2,444,608, issued July 6, 1948; the azaindenes of Heimbach and Kelly U.S. Patents 2,444,605 and 2,444,606, issued July 6, 1948; Heimbach U.S. Patents 2,444,607, issued July 6, 1948 and 2,450,397, issued September 28, 1948; Heimbach and Clark U.S.
- Patent 2,444,609 issued July 6, 1948; Allen and Reynolds U.S. Patents 2,713,541, issued July 19, 1955 and 2,743,181, issued April 24, 1956; Carroll and Beach U.S. Patent 2,716,062, issued August 23, 1955; Allen and Beilfuss U.S. Patent 2,735,769, issued February 21, 1956; Reynolds and Sagal U.S. Patent 2,756,147, issued July 24, 1956; Allen and Sagura U.S. Patent 2,772,164, issued November 27, 1956, and those disclosed by Birr in Z. wiss. Phot., vol. 47, 1952, pages 228; the quaternary benzothiazolium compounds of Brooker and Stand U.S. Patent 2,131,038, issued September 27, 1938; the disulfides of Kodak Belgian Patent 569,- 317, granted July 31, 1958; and the zinc and cadmium salts of Jones U.S. Patent 2,839,405, issued June 17, 1958.
- the emulsions can also contain speed-increasing compounds of the quaternary ammonium type of Carroll U.S. Patent 2,271,623, issued February 3, 1942; Carroll and Allen U.S. Patent 2,288,226, issued June 30, 1942; and Carroll and Spence U.S. Patent 2,334,864, issued November 23, 1943; and the polyethylene glycol type of Carroll and Beach U.S. Patent 2,708,162, issued May 10, 1955.
- the emulsion can contain a suitable gelatin plasticizer such as glycerin; a dihydroxy alkane such as 1,5-pentane diol as described in Milton and Murray U.S. Patent 2,960,404, issued November 15, 1960; an ester of an ethylene bis-glycolic acid such as ethylene bis(methyl glycolate) as described in Milton U.S. Patent 2,904,434, issued September 15, 1959; bis(ethoxy diethylene glycol) succinate as described in Gray U.S.
- a suitable gelatin plasticizer such as glycerin
- a dihydroxy alkane such as 1,5-pentane diol as described in Milton and Murray U.S. Patent 2,960,404, issued November 15, 1960
- an ester of an ethylene bis-glycolic acid such as ethylene bis(methyl glycolate) as described in Milton U.S. Patent 2,904,434, issued September 15, 1959
- bis(ethoxy diethylene glycol) succinate as described in Gray U.S.
- Patent 2,940,854 issued June 14, 1960, or a polymeric hydrosol as results from the emulsion polymerization of a mixture of an amide of an acid of the acrylic acid series, an acrylic acid ester and a styrene-type compound as described in Tong U.S. Patent 2,852,386 issued September 16, 1958.
- the plasticizer may be added to the emulsion before or after the addition of a sensitizing dye, if used.
- the emulsion can be hardened with any suitable hardener for gelatin such as formaldehyde; a halogen-substituted aliphatic acid such as mucobromic acid as described in White U.S. Patent 2,080,019, issued May 11, 1937; a compound having a plurality of acid anhydride groups such as 7,8-diphenylbicyclo(2,2,2)-7-octene-2,3,5,6-tetracarboxylic dianhydride, or a dicarboxylic or a disulfonic acid chloride such as terepht haloyl chloride or naphthalene-1,5-disulfonyl chloride as described in Allen and Carroll U.S.
- any suitable hardener for gelatin such as formaldehyde; a halogen-substituted aliphatic acid such as mucobromic acid as described in White U.S. Patent 2,080,019, issued May 11, 1937; a compound having
- Patent 2,732,316 issued January 24, 1956; a dialdehyde or a sodium bisulfite derivative thereof, the aldehyde groups of which are separated by 2-3 carbon atoms, such as fi-methylglutaraldehyde bissodium bisulfite; a bisaziridine carboxamide such as trimethylene bis(1-aziridine carboxamide) as described in Allen and Webster U.S. Patent 2,950,197, issued August 23, 1960; or 2,3-dihydroxy dioxane as described in Jetfreys U.S. Patent 2,870,013, issued January 20, 1957.
- a dialdehyde or a sodium bisulfite derivative thereof the aldehyde groups of which are separated by 2-3 carbon atoms, such as fi-methylglutaraldehyde bissodium bisulfite
- a bisaziridine carboxamide such as trimethylene bis(1-aziridine carboxamide) as described in Allen and Webster U.S. Patent 2,950,197, issued
- the emulsions can contain a coating aid such as saponin; a lauryl or oleoyl monoether of polyethylene glycol as described in Knox and Davis U.S. Patent 2,831,766, issued April 22, 1958; a salt of a sulfated and alkylated polyethylene glycol ether as described in Knox and Davis U.S. Patent 2,719,087, issued September 27, 1955; an acylated alkyl taurine such as the sodium salt of N-oleoyl-N-methyl taurine as described in Knox, Twardokus and Davis U.S.
- a coating aid such as saponin
- a lauryl or oleoyl monoether of polyethylene glycol as described in Knox and Davis U.S. Patent 2,831,766, issued April 22, 1958
- a salt of a sulfated and alkylated polyethylene glycol ether as described in Knox and Davis U.S. Patent 2,719,087, issued September 27, 1955
- Patent 2,739,891 issued March 27, 1956; the reaction product of a dianhydride of tetracarboxybutane with an alcohol or an aliphatic amine containing from 8 to 18 carbon atoms which is treated with a base, for example, the sodium salt of the monoester of tetracarboxybutane as described in Knox, Stenberg and Wilson U.S. Patent 2,843,487, issued July 15, 1958; a water-soluble maleopimarate or a mixture of a water-soluble maleopimarate and a substituted glutamate salt as described in Knox and Fowler U.S.
- Patent 2,823,123 issued February 11, 1958; an alkali metal salt of a substituted amino acid such as disodium N-(carbop-tert. octylphenoxypentaethoxy)glutamate, or a sulfosuccinarnate such as tetrasodium N-(l,2-dicarboxyethyD-N-octadecyl sulfosuccinamate, or N-lauryl disodium sulfosuccinamate.
- a substituted amino acid such as disodium N-(carbop-tert. octylphenoxypentaethoxy)glutamate, or a sulfosuccinarnate such as tetrasodium N-(l,2-dicarboxyethyD-N-octadecyl sulfosuccinamate, or N-lauryl disodium sulfos
- the thioether addenda of the invention can be used in various kinds of photographic emulsions. In addition to being useful in orthochromatic, panchromatic, and infrared sensitive emulsions, they are also useful in X-ray and other non-optically sensitized emulsions. They can be added to the emulsion before or after any optical sensitizing dyes which may be used.
- Various silver salts can be used as the sensitive salt such as silver bromide, silver iodide, silver chloride, or mixed silver halides such as silver chlorobromide or silver bromoiodide.
- the subject addenda can be used in emulsions intended for color photography, for example, emulsions containing colorforming couplers or emulsions to be developed by solutions containing couplers or other colopgenerating materials, emulsions of the mixed-packet type, such as described in Godowsky U.S. Patent 2,698,794, issued January 4, 1 955, or emulsions of the mixed-grain type, such as described in Carroll and Hanson U.S. Patent 2,592,243, issued April 8, 1952.
- Development accelerators can be utilized in developing such color emulsions including polyethylene glycols, their ester derivatives, their ether derivatives typically having the formula RO(CH CH O) H wherein R is an alkyl radical having 1 to 5 carbon atoms and wherein n is 15-100, and related derivatives.
- the subject addenda can also be used in emulsions which form latent images predominantly on the surface of the silver halide crystal or in emulsions which form latent images predominantly inside the silver halide crystal, such as those described in Davey and Knott U.S. Patent 2,592,250, issued April 8, 1952.
- the subject addenda can also be used in emulsions intended for use in diifusion transfer processes which utilize the undeveloped silver halide in the non-image areas of the negative to form a positive by dissolving the undeveloped silver halide and precipitating it on a receiving layer in close proximity to the original silver halide emulsion layer.
- diifusion transfer processes which utilize the undeveloped silver halide in the non-image areas of the negative to form a positive by dissolving the undeveloped silver halide and precipitating it on a receiving layer in close proximity to the original silver halide emulsion layer.
- gelatin In the preparation of the silver halide dispersions employed for preparing silver halide emulsions, there can be employed as the dispersing agent for the silver halide in its preparation, gelatin or some other colloidal ma terial such as colloidal albumin, a cellulose derivative, or a synthetic resin, for instance, a polyvinyl compound, although gelatin is preferred.
- colloids which can be used are polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in Lowe U.S. Patent 2,286,215, issued June 16, 1942; a far hydrolyzed cellulose ester such as cellulose acetate hydrolyzed to an acetyl content of 19- 26% as described in U.S.
- Patent 2,768,154 issued October 23, 1956; or containing cyano-acetyl groups such as the vinyl alcohol-vinyl cyanoacetate copolymer as described in Unruh, Smith and Priest US. Patent 2,808,331, issued October 1, 1957; or a polymeric material which results from polymerizing a protein or a saturated acylated protein with a monomer having a vinyl group as described in Illingsworth, Dann and Gates US. Patent 2,852,382, issued September 19, 1958. If desired, compatible mixtures of two or more of these colloids can be employed for dispersing the silver halide in its preparation.
- Typical supports for photographic elements of the invention include cellulose nitrate film, cellulose acetate film, polyvinyl acetal film, polystyrene film, polyethyleneterephthalate film and related films of resinous materials, as well as glass, paper, wood, metals and others.
- the addenda of the invention impart substantial antifoggant properties to photographic silver halide emulsions.
- the determination of the antifoggant properties of several additional addenda of the invention was carried out by the general procedure described in Example 2 except that the samples were incubated at 120 F. at 50% relative humidity for one week instead of for two weeks.
- the emulsion was a high speed negative-type gelatino-silver bromoiodide emulsion that was coated at a coverage of 355 mg. of silver and 840 mg. of gelatin per square foot on a cellulose acetate film support.
- Table D wherein the speeds and concentrations are described for Tables A, B, and C.
- EXAMPLE 4 Example 3 was repeated with two additional addenda of the invention except that the incubation period was two weeks instead of one week.
- the addenda of the invention can also be utilized as built-in fixers for photographic silver halide emulsions when utilized in amounts of at least about equal to the silver halide in the emulsion on a molar basis. Such is illustrated by Examples 5 and 6 below.
- EXAMPLE 5 To a photographic gelatino-silver bromide high speed negative-type emulsion containing .05 mole of silver bromide per 40 grams of a 6.3% aqueous solution of gelatin was added Addenda #4 in an amount equal to about 1.2 moles thereof per mole of silver bromide which was then coated at a coverage of 10 cc. of the emulsion per 5 inch by 14 inch of surface on a cellulose acetate film support. The resulting film was then exposed through a negative for seconds at 34 inches with a 60 watt light bulb. The film was then developed for 10 minutes at 68 F. in a developer having the formula:
- Example 5 was repeated except that 2 moles of Addenda #3 per mole of silver bromide were utilized in lieu of Addenda #4.
- Addenda #4 was utilized in lieu of Addenda #4.
- the unexposed areas of the developed film had a slight yellow cast which did not darken upon prolonged exposure to ordinary room illumination.
- the present invention thus provides new and useful photographic silver halide emulsions, and which emulsions have improved antifoggant properties and self fixing properties.
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE621605D BE621605A (ko) | 1961-08-25 | ||
US133768A US3140178A (en) | 1961-08-25 | 1961-08-25 | Photographic silver halide emulsions containing thioether derivatives as antifoggants and stabilizers |
FR907405A FR1347695A (fr) | 1961-08-25 | 1962-08-21 | Nouvelle émulsion photographique aux halogénures d'argent contenant certains thio-composés |
DEE23427A DE1173796B (de) | 1961-08-25 | 1962-08-23 | Photographische Silberhalogenidemulsion und photographisches, eine solche Emulsion enthaltendes Material |
GB32854/62A GB1010563A (en) | 1961-08-25 | 1962-08-27 | Improvements in or relating to silver halide photographic materials |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US133768A US3140178A (en) | 1961-08-25 | 1961-08-25 | Photographic silver halide emulsions containing thioether derivatives as antifoggants and stabilizers |
Publications (1)
Publication Number | Publication Date |
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US3140178A true US3140178A (en) | 1964-07-07 |
Family
ID=22460224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US133768A Expired - Lifetime US3140178A (en) | 1961-08-25 | 1961-08-25 | Photographic silver halide emulsions containing thioether derivatives as antifoggants and stabilizers |
Country Status (5)
Country | Link |
---|---|
US (1) | US3140178A (ko) |
BE (1) | BE621605A (ko) |
DE (1) | DE1173796B (ko) |
FR (1) | FR1347695A (ko) |
GB (1) | GB1010563A (ko) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3301678A (en) * | 1964-05-28 | 1967-01-31 | Eastman Kodak Co | Process for stabilizing photographic images with heat |
US3506444A (en) * | 1964-05-28 | 1970-04-14 | Eastman Kodak Co | Dry stabilization of photographic images |
US3844788A (en) * | 1973-04-02 | 1974-10-29 | Eastman Kodak Co | Incorporation of sulfonyl derivatives of isothiourea in light-sensitive elements |
US4132551A (en) * | 1971-09-17 | 1979-01-02 | Agfa-Gevaert N.V. | High temperature processing of photographic silver halide material |
US4307175A (en) * | 1979-09-28 | 1981-12-22 | Agfa-Gevaert, N.V. | Photographic silver halide emulsion material containing an antifoggant precursor |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3043690A (en) * | 1960-10-12 | 1962-07-10 | Polaroid Corp | Novel photographic products, compositions, and processes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE957183C (de) * | 1953-07-01 | 1957-01-31 | Eastman Kodak Co | Stabilisiertes photographisches Material |
-
0
- BE BE621605D patent/BE621605A/xx unknown
-
1961
- 1961-08-25 US US133768A patent/US3140178A/en not_active Expired - Lifetime
-
1962
- 1962-08-21 FR FR907405A patent/FR1347695A/fr not_active Expired
- 1962-08-23 DE DEE23427A patent/DE1173796B/de active Pending
- 1962-08-27 GB GB32854/62A patent/GB1010563A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3043690A (en) * | 1960-10-12 | 1962-07-10 | Polaroid Corp | Novel photographic products, compositions, and processes |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3301678A (en) * | 1964-05-28 | 1967-01-31 | Eastman Kodak Co | Process for stabilizing photographic images with heat |
US3506444A (en) * | 1964-05-28 | 1970-04-14 | Eastman Kodak Co | Dry stabilization of photographic images |
US4132551A (en) * | 1971-09-17 | 1979-01-02 | Agfa-Gevaert N.V. | High temperature processing of photographic silver halide material |
US3844788A (en) * | 1973-04-02 | 1974-10-29 | Eastman Kodak Co | Incorporation of sulfonyl derivatives of isothiourea in light-sensitive elements |
US4307175A (en) * | 1979-09-28 | 1981-12-22 | Agfa-Gevaert, N.V. | Photographic silver halide emulsion material containing an antifoggant precursor |
Also Published As
Publication number | Publication date |
---|---|
FR1347695A (fr) | 1964-01-04 |
DE1173796B (de) | 1964-07-09 |
BE621605A (ko) | |
GB1010563A (en) | 1965-11-17 |
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