US3057725A - Substituted disulfides as antifoggants for silver halide emulsions - Google Patents

Substituted disulfides as antifoggants for silver halide emulsions Download PDF

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US3057725A
US3057725A US827716A US82771659A US3057725A US 3057725 A US3057725 A US 3057725A US 827716 A US827716 A US 827716A US 82771659 A US82771659 A US 82771659A US 3057725 A US3057725 A US 3057725A
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emulsions
issued
silver halide
disulfides
class consisting
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US827716A
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Arthur H Herz
Norman W Kalenda
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE593047D priority Critical patent/BE593047A/xx
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Priority to US827716A priority patent/US3057725A/en
Priority to FR832881A priority patent/FR1269367A/fr
Priority to DEE19625A priority patent/DE1188941B/de
Priority to GB24890/60A priority patent/GB956277A/en
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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

Definitions

  • This invention relates to the stabilization of photographic silver halide emulsions, and more particularly, to a method of inhibiting development of spontaneous fog without adversely affecting the sensitivity of the photographic silver halide emulsions.
  • Fog usually appears over the whole area of the sensitive coating, but when severe, it frequently is non-uniform. Fog may also be caused by exposure to chemicals, for example, hydrogen sulfide and other reactive sulfur compounds, hydrogen peroxide vapor, and strongly reducing materials. While antifoggants and stabilizers may protect, to some extent, against such effects, it is normally understood that antifoggants protect against spontaneous growth of fog during prolonged storage or storage at high temperatures and humidities, or during development to maximum contrast and speed, or both.
  • Such disulfides having both sensitizing and some stabilizing activity cannot be employed in unsensitized or under- "ice ing photographic silver halide emulsions without affecting to any material extent the sensitivity of the emulsions.
  • Another object is to provide a method of stabilizing both unsensitized and sensitized emulsions, without introducing any substantial sensitizing or desensitizing effects.
  • Still another object is to provide new organic disulfides and a method of preparation. Other objects will become ap parent from a consideration of the following description and examples.
  • photographic silver halide emulsions can be stabilized and the development of spontaneous fog substantially inhibited by incorporating therein certain organic disulfides.
  • organic disulfides useful in practicing our invention comprise compounds selected from those represented by the following general formula:
  • R and R each represents a methylene group (which may or may not be substituted by hydrocarbon radicals, such as methyl, ethyl, phenyl, tolyl, etc., i.e., a hydrocarbon radical containing from 1 to 7 carbon atoms), m and n each represents a positive integer of from about 1 to 6 and X and Y each represent a radical:
  • R represents an alkoxy group (e.g., methoxyl, ethoxyl, etc.), an amine group (NI-I an alkylamino group (e.g., methylamino, ethylamino, etc.), a dialkylamino group (e.g., dimethylamino, diethylamino, etc.), or an -OM group wherein M represents a cation (.e.g., hydrogen, sodium, potassium, ammonium, p idinium, triethanolammonium, guanidinium, etc.), R" presents a hydrogen atom, an alkyl group (e.g., me ethyl, propyl, isopropyl, butyl, etc.) or an aralkyl gro p"f(e.g., benzyl, ,B-phenylethyl, etc.), R represents an acyl group (e.g., methoxyl, ethoxyl
  • Typical organic'disulfides embraced by the above general formula include, for example, the following:
  • An aqueous or organic solution of the disulfides of our invention when added at suitable concentration to unsensitized, chemically sensitized, or optically sensitized photographic emulsions does not appreciably affect the sensitometn'c values for sensitivity and fog when measurements are made soon after coating.
  • the disulfides of our invention do stabilize speed and maintain fog at a low level.
  • the preparation of silver halide emulsions involves three separations: (1) the emulsification and digestion or ripening of the silver halide, (2) the freeing of the emulsion from excess soluble salts, usually by washing, and (3) the second digestion or after-ripening to obtain increased sensitivity (Mees, The Theory of the Photographic Process (1942)).
  • disulfides of our invention can be incorporated in the emulsions without adverse effects by bathing techniques known to those skilled in the art.
  • photographic emulsions used in practicing our invention are of the developing-out type.
  • the emulsions can be chemically sensitized by any of the accepted procedures.
  • the 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; Sheppard et a1.
  • the emulsions can also be treated with salts of the noble metals such as ruthenium, rhodium, palladium, iridium, and platinum.
  • 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.
  • the emulsions can also be chemically sensitized with gold salts as described in Waller et al. U.S. Patent 2,399,- 083, issued April 23, 1946, or stabilized with gold salts as described in Damschroder U.S. Patent 2,597,856, issued May 27, 1952, and Yutzy and Leermakers U.S. Patent 4 2,597,915, issued May 27, 1952.
  • Suitable compounds are potassium chloroaurite, potassium aurithiocyanate, potassium chloroaurate, auric trichloride and Z-aurosulfobenzothiazole methochloride.
  • the emulsions can also be chemically sensitized with reducing agents such as stannous salts (Carroll U.S. Patent 2,487,850, issued November 15, 1949), polyamines, such as diethyl 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(fl-aminoethyl)sulfide and its water-soluble 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 diethyl 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(fl-a
  • 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 may also contain speed-increasing com- .
  • com- speed-increasing com- .
  • the emulsions may 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. application .Serial No. 588,951, filed June 4, 1956; an ester of an ethylene bis-glycolic acid such as ethylene bis(methyl glycolate) as described in Milton U.S. application Serial No. 662,564, filed May 31, 1957; bis-(ethoxy diethylene glycol) succinate as described in Gray U.S. application Serial No.
  • the emulsions may 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 terephthaloyl chloride or naphthalene-1,5-disulfonyl chloride as described in Allen and Carroll U.S. Patents 2,725,294 and 2,725,295, both issued November 29, 1955; a cyclic 1,2-diketone such as cyclopentane-l,2-dione as described in Allen and Byers U.S.
  • any suitable hardener for gelatin such as formaldeh
  • a bis-aziridine carboxamide such as trimethylene bis(1-aziridine carboxamide) as described in Allen and Webster U.S. patent application Serial No. 599,891, filed July 25, 1956; or 2,3-dihydroxy dioxane as described in J efi'reys U.S. Patent 2,870,013, issued January 20, 1959.
  • the emulsions may contain a coating aid such as saponin; a lauryl or oleyl monoether of polyethylene glycol as described in Knox and Davis U.S. Patent 2,83 1,7 66, 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 oleyl monoether of polyethylene glycol as described in Knox and Davis U.S. Patent 2,83 1,7 66, 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-(carbo-p-tert. octylphenoxypentaethoxy)glutamate as described in Knox and Wilson U.S. patent application Serial No. 600,679, filed July 30, 1956; or a sulfosuccinamate such as tetrasodium N-(1,2-dicarboxyethyl)-N-octadecyl sulfosuccinamate or N-lauryl disodium sulfosuccinamate as described in Knox and Stenber U.S. patent application Serial No. 691,125, filed October 21, 1957.
  • the addenda which we have described may be used in various kinds of photographic emulsions. In addition to being useful in X-ray and other nonoptically sensitized emulsions they may also be used in orthochromatic, panchromatic, and infrared sensitive emulsions. They may be added to the emulsion before or after any sensitizing dyes which are used.
  • Various silver salts may be used as the sensitive salts such as silver bromide, silver iodide, silver chloride, or mixed silver halides such as silver chlorobromide or silver bromoiodide.
  • The'agents may be used in emulsions intended for color photography, for example, emulsions containing color-forming couplers or emulsions to be developed by solutions containing couplers or other color-generating materials, emulsions of the mixed-packet type, such as described in Godowsky US. Patent 2,698,794, issued January 4, 1955; or emulsions of the mixed-grain type, such as described in Carroll and Hanson U.S. Patent 2,592,243, issued April 8, 1952.
  • These agents 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 dispersing agent for the silver halide in its preparation gelatin or some other colloidal material such as colloidal albumin, a cellulose derivative, or a synthetic resin, for instance, a polyvinyl compound.
  • colloidal albumin colloidal albumin
  • a cellulose derivative a cellulose derivative
  • synthetic resin for instance, a polyvinyl compound.
  • colloids which may 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 1926% 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 U.S. 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 U.S. Patent 2,852,382, of Illingsworth, Dann and Gates, issued September 16, 1958.
  • cyano-acetyl groups such as the vinyl alcohol-vinyl cyanoacetate copolymer as described in Unruh, Smith and Priest U.S. 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 U.S. Patent 2,852,382, of Illingsworth, Dann and Gates, issued September 16, 1958.
  • compatible mixtures of two or more of these colloids may be employed for dispersing the silver halide in its preparation.
  • Combinations of these sensitizers, hardeners, etc., may be used.
  • the organic disulfides useful in practicing our invention can be added to the photographic emulsions prior to the final digestion, if desired. Generally, these compounds can be added from a substantially neutral solution so that the pH of the emulsion is not disturbed. In the case of compounds containing free sulfonic acid groups, this means that these sulfonic acid groups may be at least partially neutralized. However, where it is desired to stabilize an acidic emulsion, it is obviously not necessary that the antifoggant be added from substantially neutral solutions. Since the disulfides of our invention can be added to the emulsions in such small quantities, it is apparent that they will generally have no adverse effect upon the pH of the emulsions.
  • organic disulfides useful in practicing our invention can be added to the emulsions in the form of substantially neutral aqueous solutions. If a particular'disulfide does not have sufiicient solubility in Water, addition to the emulsion can be made in the form of awatermiscible organic solvent, such as methanol, ethanol, dioxane, pyridine, etc. v l
  • the amount of disulfide compound added to the emulsions of our invention can be varied, depending upon the particular emulsion, the silver halide content of the emulsion, etc. In general, we have found that from about 0.1 to 15.0 grams of disulfide per mole of silver halide can advantageously be employed in our invention.
  • One of the outstanding advantages of the disulfides of our invention, as compared with the disulfides which have been previously described in the prior art, is that they can be used in quite substantial quantities without introducing serious desensitizing eifects.
  • the disulfides useful in our invention advantageously have little or no sensitizing action of their own, and hence, they can be used to stabilize emulsions which have already been finished to their optimum or near-optimum speeds.
  • addition of our compounds to such finished emulsions does not result in any substantial desensitizing effect, such as might ordinarily be expected.
  • Fresh tests and incubation tests (one week at 120 F., constant relative humidity of about 50%, and in some cases for two weeks under the same conditions) were also run for the same emulsion series with development under the same conditions. The relative speed and fog for each of the series coatings were then measured, the speed being determined at a point about 0.3 density above fog.
  • disulfides useful in stabilizing emulsions according to our invention can be obtained by methods which have been previously described in the prior art.
  • the disulfides of Formula IA can be obtained by simple oxidation of the corrseponding mercapto-substituted sulfonic acid or derivative. Oxidation can conveniently be accomplished by simply contacting the mercapto derivative with an oxidizing agent, such as hydrogen peroxide, sodium perchlorate, etc. The following examples will serve to illustrate this technique.
  • the disulfides of Formula IB can be prepared by simply acylating the corresponding amino compound. Acylation can be accomplished by merely contacting the corresponding amino-disulfide with an acylhalide. In like manner, the disulfides of Formula IC, wherein R represents an acyl group, can be obtained by merely acylating the corresponding compounds of Formula 1C, wherein R represents a hydrogen atom. Techniques of acylation are well known to those skilled in the art and no particular 'linowedge is required in order to acylate the amino or hydroXyl-substituted organic disulfides.
  • R represents an alkylene group having from 1 to about 6 carbon atoms and X represents a radical selected from the class consisting of SO R and OR wherein R represents a member selected from the class consisting of an alkoxyl group having from 1 to about 6 carbon atoms and a OM group wherein M represents a cation, R represents a member selected from the class consisting of a hydrogen atom and an alkyl group having from 1 to about 6 carbon atoms, R, represents an acyl group of an organic acid selected from the class consisting of carboxylic acids and sulfonic acids, and R represents a member selected from the class consisting of a hydrogen atom, an alkyl group having from 1 to about 6 carbon atoms and an acyl group of an organic acid selected from the class consisting of carboxylic acids and sulfonic acids.
  • R represents an alkylene group having from 1 to about 6 carbon atoms
  • R represents a member selected from the class consisting of an alkoXyl group having from 1 to about 6 carbon atoms and a OM group wherein M represents a cation.
  • R represents an alkylene group having from 1 to about 6 carbon atoms
  • R represents a member selected from the class consisting of a hydrogen atom, an alkyl group having from 1 to about 6 carbon atoms
  • R represents an acyl group of an organic acid selected from the class consisting of carboxylic acids and sulfonic acids.
  • m represents a positive integer of from about 1 to 6 and R represents a member selected from the class consisting of an alkoxyl group having from 1 to about 6 carbon atoms and a OM group wherein M represents a cation.
  • R represents a member selected from the class consisting of a hydrogen atom and an alkyl group having from 1 to about 6 carbon atoms and R represents an acyl group of an organic acid selected from the class consisting of carboxylic acids and sulfonic acids.
  • R represents an alkylene group having from 1 to about 6 carbon atoms and M represents a cation.
  • R represents an alkylene group having from 1 to about 6 carbon atoms and R represents an acyl group of an organic acid selected from the class consisting of carboxylic acids and sulfonic acids.
  • R represents an alkylene group having from 2 to about 6 carbon atoms.
  • R represents an alkylene group having from 2 5 A p gr ph a halide ls n Stabilized to about 6 carbon atoms and R represents an acyl group With 2,2'-di(benlenesulfonamidmdiethyldisulfideof an organic acid selected from the class consisting of carboxylic acids and sulfonic acids References Cited in the file of this patent 12.

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  • Physics & Mathematics (AREA)
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US827716A 1959-07-17 1959-07-17 Substituted disulfides as antifoggants for silver halide emulsions Expired - Lifetime US3057725A (en)

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Application Number Priority Date Filing Date Title
BE593047D BE593047A (xx) 1959-07-17
US827716A US3057725A (en) 1959-07-17 1959-07-17 Substituted disulfides as antifoggants for silver halide emulsions
FR832881A FR1269367A (fr) 1959-07-17 1960-07-13 Nouvelle émulsion photographique stabilisée
DEE19625A DE1188941B (de) 1959-07-17 1960-07-16 Stabilisierte photographische Halogensilberemulsion
GB24890/60A GB956277A (en) 1959-07-17 1960-07-18 Improvements in photographic silver halide emulsions

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3640715A (en) * 1968-12-23 1972-02-08 Agfa Gevaert Ag Photographic silver halide emulsion containing as a sensitizer bio-quarternary salts of bis-aminoalkyl-disulfides
US3647469A (en) * 1968-12-23 1972-03-07 Agfa Gevaert Ag Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions
US3926632A (en) * 1971-09-13 1975-12-16 Agfa Gevaert Nv Photographic silver halide lith material
US4120726A (en) * 1975-04-15 1978-10-17 Veb Filmfabrik Wolfen Silver-halide emulsion sensitized with an asymmetrical disulfide
US5217859A (en) * 1992-04-16 1993-06-08 Eastman Kodak Company Aqueous, solid particle dispersions of dichalcogenides for photographic emulsions and coatings
US5219721A (en) * 1992-04-16 1993-06-15 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
US5356770A (en) * 1992-05-29 1994-10-18 Eastman Kodak Compamn Color photographic materials and methods with stabilized silver chloride emulsions
US5364754A (en) * 1992-04-16 1994-11-15 Eastman Kodak Company Silver halide photographic emulsions precipitated in the presence of organic dichalcogenides
US5415992A (en) * 1993-11-30 1995-05-16 Eastman Kodak Company Heat stabilized silver chloride photographic emulsions containing phosphine compounds
US5418127A (en) * 1993-05-28 1995-05-23 Eastman Kodak Company Water-soluble disulfides in silver halide emulsions
US5443947A (en) * 1993-11-30 1995-08-22 Eastman Kodak Company Heat stabilized silver chloride photographic emulsions containing thiosulfonate/sulfinate compounds
US5601970A (en) * 1995-01-03 1997-02-11 Eastman Kodak Company Photographic elements exhibiting improved stability
US5652090A (en) * 1996-03-15 1997-07-29 Eastman Kodak Company Silver halide photographic elements containing dithiolone compounds
JP2008513503A (ja) * 2004-09-21 2008-05-01 バイオニューメリック・ファーマスーティカルズ・インコーポレイテッド 医薬用ジスルフィド塩

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2438716A (en) * 1944-10-06 1948-03-30 Gen Aniline & Film Corp Stabilized silver halide emulsions
US2440206A (en) * 1944-09-16 1948-04-20 Gen Aniline & Film Corp Stabilized silver halide emulsions
US2739060A (en) * 1952-11-08 1956-03-20 Eastman Kodak Co Chemical sensitization of photographic emulsions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE874702C (de) * 1945-12-15 1953-04-27 Gen Aniline & Film Corp Stabilisatoren fuer photographische Emulsionen
DE957183C (de) * 1953-07-01 1957-01-31 Eastman Kodak Co Stabilisiertes photographisches Material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440206A (en) * 1944-09-16 1948-04-20 Gen Aniline & Film Corp Stabilized silver halide emulsions
US2438716A (en) * 1944-10-06 1948-03-30 Gen Aniline & Film Corp Stabilized silver halide emulsions
US2739060A (en) * 1952-11-08 1956-03-20 Eastman Kodak Co Chemical sensitization of photographic emulsions

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3640715A (en) * 1968-12-23 1972-02-08 Agfa Gevaert Ag Photographic silver halide emulsion containing as a sensitizer bio-quarternary salts of bis-aminoalkyl-disulfides
US3647469A (en) * 1968-12-23 1972-03-07 Agfa Gevaert Ag Bisaminoalkyl disulfides as sensitizers and stabilizers for silver halide emulsions
US3926632A (en) * 1971-09-13 1975-12-16 Agfa Gevaert Nv Photographic silver halide lith material
US4120726A (en) * 1975-04-15 1978-10-17 Veb Filmfabrik Wolfen Silver-halide emulsion sensitized with an asymmetrical disulfide
EP0566080A3 (en) * 1992-04-16 1995-01-04 Eastman Kodak Co Photographic silver halide emulsions sensitized in the presence of organic dichalcogenides.
US5219721A (en) * 1992-04-16 1993-06-15 Eastman Kodak Company Silver halide photographic emulsions sensitized in the presence of organic dichalcogenides
US5364754A (en) * 1992-04-16 1994-11-15 Eastman Kodak Company Silver halide photographic emulsions precipitated in the presence of organic dichalcogenides
US5217859A (en) * 1992-04-16 1993-06-08 Eastman Kodak Company Aqueous, solid particle dispersions of dichalcogenides for photographic emulsions and coatings
US5356770A (en) * 1992-05-29 1994-10-18 Eastman Kodak Compamn Color photographic materials and methods with stabilized silver chloride emulsions
US5418127A (en) * 1993-05-28 1995-05-23 Eastman Kodak Company Water-soluble disulfides in silver halide emulsions
US5415992A (en) * 1993-11-30 1995-05-16 Eastman Kodak Company Heat stabilized silver chloride photographic emulsions containing phosphine compounds
US5443947A (en) * 1993-11-30 1995-08-22 Eastman Kodak Company Heat stabilized silver chloride photographic emulsions containing thiosulfonate/sulfinate compounds
US5601970A (en) * 1995-01-03 1997-02-11 Eastman Kodak Company Photographic elements exhibiting improved stability
US5652090A (en) * 1996-03-15 1997-07-29 Eastman Kodak Company Silver halide photographic elements containing dithiolone compounds
JP2008513503A (ja) * 2004-09-21 2008-05-01 バイオニューメリック・ファーマスーティカルズ・インコーポレイテッド 医薬用ジスルフィド塩
EP1797031A4 (en) * 2004-09-21 2009-12-16 Bionumerik Pharmaceuticals Inc DISULFIDE SALTS FOR MEDICAL USE

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DE1188941B (de) 1965-03-11
GB956277A (en) 1964-04-22

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