US3403025A - Desensitization of silver halides to visible radiation with thiuram disulfides - Google Patents

Desensitization of silver halides to visible radiation with thiuram disulfides Download PDF

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Publication number
US3403025A
US3403025A US482632A US48263265A US3403025A US 3403025 A US3403025 A US 3403025A US 482632 A US482632 A US 482632A US 48263265 A US48263265 A US 48263265A US 3403025 A US3403025 A US 3403025A
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silver halide
visible radiation
photographic
disulfide
piazine
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US482632A
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William W Rees
William H Russell
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US482632A priority Critical patent/US3403025A/en
Priority to FR73401A priority patent/FR1490050A/fr
Priority to BE685779D priority patent/BE685779A/xx
Priority to DE19661547727 priority patent/DE1547727B1/de
Priority to GB38128/66A priority patent/GB1155053A/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
    • G03C1/36—Desensitisers
    • 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
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation

Definitions

  • This invention relates to reducing the sensitivity of silver halides to visible radiation and compositions which are useful for this purpose.
  • this invention relates to photographic silver halide emulsions and elements which can be used in radiography.
  • this invention relates to X-ray sensitive photographic elements which have materially reduced sensitivity to visible radiation.
  • photographic'silver halides particularly those employed in photographic silver halide emulsions designed for use in radiography, can be substantially desensitized to visible radiation without substantially affecting their sensitivity to X-rays.
  • US. Patent 3,184,313, issued May 18, 1965 discloses the use of thiuram disulfides to reduce the sensitivity of photographic silver halide emulsions to visible radiation.
  • the thiuram disulfide silver halide desensitizers have the advantage of only slightly lowering the sensitivity of X-ray sensitive elements to X-rays while materially reducing their sensitivity to visible radiation.
  • X-ray sensitive elements containing these thiuram disulfides can be easily handled under ordinary safelight conditions while dry.
  • X-ray sensitive elements containing thiuram disulfides are not completely protected against visible radiation while wet, i.e., during processing. It is evident that it would be desirable to protect X-ray sensitive elements against the adverse effects of visible light during all stages of handling, i.e., in both dry and wet stages.
  • the aforementioned combination is employed to desensitize a photographic silver halide emulsion to visible radiation.
  • Another embodiment of this invention relates to a photographic element comprising a support and a photographic silver halide layer desensitized to visible radiation with a combination of a thiuram disulfide silver halide desensitizer and a piazine containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically.
  • a significant feature of this invention is that the thiuram disulfide silver halide desensitizer and the piazine must be used in combination to protect X-ray sensitive materials from the adverse effects of visible radiation during all stages of handling, i.e., in the dry and wet stages, and also to stabilize the X-ray speed of the element during storage.
  • the thiuram disulfides are effective to stabilize the speed and fog of a silver halide emulsion during dry handling but they do not give good X-ray speed stability during storage.
  • the piazine imparts good wet stability but gives very poor incubation speed stability.
  • the disulfide compounds employed in the pnactice of this invention are thiuram disulfide silver halide desensitizers.
  • Typical thiuram disulfide silver halide desensitizers are disclosed in US. Patent 3,184,313, issued May 18, 1965. These compounds are characterized by marked desensitizing action toward silver halide emulsions insofar as their sensitivity to visible radiation is concerned (particularly in the blue region of the spectrum) while retaining substantially the sensitivity of the emulsions to X-rays.
  • the concentration of thiuram disulfide silver halide desensitizer employed is subject to wide variation depending upon the particular silver halide used, the amount of gelatin or other colloidal binder and other variables.
  • thiuram disulfide employed in the practice of this invention is in the range of about 20 to about 30 mg. of thiuram disulfide per mole of silver halide.
  • silver halide desensitizers are employed in combination with the piazines described herein.
  • thiuram disulfide While the concentration of the thiuram disulfide and the piazine in the combination can be widely varied, it is prefer-red that the major component of the combination be thiuram disulfide, useful results being obtained with combinations in which the weight ratio of thiuram disulfide to piazine is in the range of about 2:1 to about 20: 1, preferably about 2:1 to about 10:1.
  • Typical thiuram disulfide desensitizers which can be employed in the practice of this invention include those represented by the following general formula:
  • R and R each represents an alkyl group, such as methyl, ethyl, propyl, butyl isobutyl, etc. (e.g., an alkyl group containing from 1 to 4 carbon atoms), an aryl group, such as phenyl, tolyl, etc., or together R and R represent the atoms necessary to complete an azine ring, such as morpholine, piperidine, etc., or, alternatively, a pyrrolidine ring, for example.
  • the thiuram disulfide compounds are characterized in that the nitrogen atoms thereof are tertiary nitrogen atoms. Typical compounds included by the above general formula are, for example, the following:
  • the piazines employed in the practice of this invention are heterocyclic compounds having two nitrogen atoms in the para position.
  • the pi azines contain a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically and can be in the free or quaternized form.
  • a piazine containing a pyrazine ring to which two 6membere-d carbocyclic rings are fused symmetrically it is intended to include the compound in its free or quaternized form.
  • the pyrazine ring in the piazine is fused to two symmetrical carbocyclic rings which can be unsubstituted, as in phenazine, or substituted by a variety of substituents including one or more other carbocyclic rings, for example, one or two fused aromatic rings as in naphtho-phenazine and naphthazine.
  • substituents which can be present to form the resulting substituted phenazines or napthazines include amino, hydroxy, methyl amino, ethyl amino, meth yl, ethyl, dodecyl, carboxyethyl, sulfopropyl, sulfobutyl, phenyl, benzyl, acetyl, and the like. It is obvious that the nature of the substituents on the two 6-membered fused rings in the piazine is subject to wide variation. However, it can be seen that these piazines are characterized by a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically.
  • Piazines which are particularly useful in the practice of this invention can be represented by the following formulas:
  • each of R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring and each n is an integer of 0 to 2.
  • R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6- membered carbocyclic ring
  • R is alkyl, hydroxyalkyl or aryl
  • X is an anion
  • each n is an integer of (l to 2
  • z is an integer of 0 to l.
  • the piazines containing other rings which are fused to the 6-rnembered carbocyclic rings which are in turn fused to the pyrazine ring can also be represented by the formula:
  • each of a, b, c and d is an integer of 0 to 1 and each Z represents the non-metallic atoms necessary to form a 6-membered carbocyclic ring,
  • R is alkyl, hydroxyalkyl or aryl
  • z is an integer of O to 1
  • X is an anion such as halogen, chlorate, sulfate, methyl sulfate, p-toluene sulfonate and the like.
  • the concentration of piazine employed in the practice of this invention is subject to wide variation. In general, however, quite useful results can be obtained with concentrations in the range of about 1 to about 50, preferably about 2 to about 10 mg. per mole of silver halide. As previously indicated, it is preferred that the desensitizing combination contain a minor portion of the piazine in comparison to the thiuram disulfide.
  • Typical piazines which can be employed in the practice of this invention include the following:
  • silver halides such as silver chlo ride, silver bromide, silver chlorobromide, and the like can be employed in practicing this invention although iodide containing photographic silver halide emulsions are especially useful.
  • emulsions include silver bromoiodide, silver chloroiodide, silver chlorobromide and the like.
  • Photographic silver halide emulsions which form the latent image predominantly Within the silver halide grain can be usefully employed in the practice of this invention.
  • Such internal latent image emulsions are described in Davey and Knott U.S. Patent 2,592,250 issued Apr. 8, 1952.
  • the photographic silver halides desensitized according to the practice of this invention can be dispersed in any of the conventional hydrophilic water permeable binding materials, particularly those employed in the preparation of photographic silver halide emulsions and elements, as exemplified by gelatin, colloidal albumin, cellulose derivatives, synthetic resins such as polyvinyl coumpounds, acrylamide polymers and the like as well as mixtures of these materials.
  • binding materials are generally employed in coating photographic silver halides on supports.
  • photographic silver halides which are coated in the absence of such binding materials for example, those coated by vacuum deposition, can be readily desensitized according to the practice of this invention.
  • the photographic silver halides employed in the practice of this invention can be coated on a wide variety of supports in preparing photographic elements.
  • the silver halides can be coated on one or both sides of the support, which is preferably transparent and flexible.
  • Typical supports are cellulose nitrate film, cellulose ester film, polyvinyl acetal film, polystyrene film, polyethylene terephthalate film, and related films or resinous materials as well as glass, paper, metal and the like.
  • Supports such as paper which are coated with a-olefin polymers, particularly polymers of a-olefins containing two or more carbon atoms, as exemplified by polyethylene, polypropylene, ethylene-butene copolymers and the like, can also be employed.
  • a small amount of a light-absorbing organic dye can be employed either in the emulsion or in an overcoating layer. Since the silver halide emulsions of our invention may retain some sensitivity in the blue region of the spectrum, it has been found that many azo dyes, such as tartrazine, can be usefully employed.
  • visible radiation absorbing dyes which can be employed in such arrangements are 2-(2-methoxy styryl) quinoline hydrochloride, the condensation product of two molecular proportions of quinaldine methosulfate and one molecular proportion of 4,4-diphenyl dialdehyde pyridine, 4,4- methenyl bis (1 naphthyl-3-methylpyrazoline-5 etc.
  • Other light-absorbing dyes are described in Dostes and Pfafi U.S. application Ser. No. 83,709, filed Ian. 19, 1961.
  • the amount of light-absorbing dye used to reduce the sensitivity of our photographic elements can vary as de scribed in said U.S. application Ser. No. 83,709.
  • a dyed silver halide emulsion layer or a dyed overcoating layer to protect further the radiographic sensitive layer
  • a light-absorbing silver halide emulsion layer which has very low sensitivity to visible radiation. Lippmann-type emulsions can conveniently be employed for this purpose. Silver iodide-containing emulsion layers are also useful for this purpose.
  • the photographic silver halide emulsions described herein can be chemically sensitized with compounds of the sulfur group, noble metal salts such as gold salts, reduction sensitized with reducing agents, and combinations of these.
  • emulsion layers and other layers present in photographic elements made according to this invention can be hardened with any suitable hard ener such as aldehyde hardeners, aziridine hardeners, hardeners which are derivatives of dioxane, oxypolysaccharides such as oxystarch, oxy plant gums, and the like.
  • the photographic silver halide emulsions can also contain additional additives, particularly those known to be beneficial in photographic emulsions, including, for example, stabilizers or antifoggants, particularly the water soluble inorganic acid salts of cadmium, cobalt, manganese and zinc as disclosed in U.S. Patent 2,829,404, the substituted triazaindolizines as disclosed in U.S. Patents 2,444,605 and 2,444,607, speed increasing materials, plasticizers and the like.
  • Sensitizers which give particularly good results in photographic compositions are the alkylene oxide polymers which can be employed alone or in combination with other materials, such as quaternary ammonium salts, as disclosed in U.S. Patent 2,886,437 or with mercury compounds and nitrogen containing compounds, as disclosed in U.S. Patent 2,751,299.
  • EXAMPLE 1 As already indicated, the thiuram disulfides or piazines alone, will not combine good X-ray speed stability during storage with protection against visible radiation during both wet and dry handling.
  • each of the three portions of emulsion is coated on an ordinary cellulose acetate film support and the coatings are dried. The coatings are then divided into five samples, each of which is tested in the following manner:
  • Test l.--Exposure to kv. X-rays Processed for 6 minutes in an ordinary MQ developer, i.e., a developer containing hydroquinone and N-methyl-p-aminophenol sulfate, such as Kodak Developer D-19b to which is added a small concentration of alkali to increase the pH to about 11.0. After development, the samples are fixed, washed and dried in the usual manner. The speeds of the samples are measured at a density of 0.85 above fog, the
  • Test 2 A low-intensity light exposure of 60 seconds in an intensity scale sensitometer to a 500-watt bulb of the type normally used in radiography, but having a greater sensitivity than the emulsion described in Example 1, is prepared and divided into eight portions. These portions of emulsionare then treated as described below:
  • Test 3 The samples are incubated for 2 weeks at Portion Treatment 120 F., 50% relative humidity before exposure and I N further t eatment. Control. processing as describedinTest 2. II 20 mg. 1,3-diamino methylphenazinium Test 4.Dry safelight test. This test consists of exchloride per mole of silver halide. posure of the dry element to a safelight containing a 25- III 30.6 mg. of bis(morpholinothiocarbamyl) diwatt bulb modulated by a Morlite Filter I-11814 (desulfide per mole of silver halide. scribed hereinafter) for 16 minutes at a distance of two IV 30.6 mg.
  • the combination of thiuram disulfides and piazlnes n described herein impart to photographic silver halide ele VII of bls(morpt.lolmothl.ocarbamyl) sulfide per mole of silver halide plus 4.0 mg.
  • ments and emulsions good X-ray speed stability upon of 13 diamino 5 eth l henazinium hloride storage and protection against visible radiation during er of Sn erh y c both wet and dry handling.
  • Kodak Developer D19b has the following composi tion:
  • this developer is found most effective when the pH is raised slightly to 11.0 by the addition of additional alkali.
  • the Morlite 1-11814 Safelight Filter transmits visible radiation principally between about 540 and 700 m with maximum transmission at from about 580 to 700 (density of about 0.1 in this range).
  • this invention makes it possible to protect X-ray sensitive elements from the adverse effects of visible radiation in all stages of processing, i.e., in both the dry and wet stages.
  • a photographic silver halide emulsion desensitized to visible radiation with a thiuram disulfide silver halide desensitizer and a piazine containing a pyrazine ring to which two 6-mernbered carbocyclic rings are fused symmetrically.
  • a photographic silver halide emulsion desensitized to visible radiation with a thiuram disulfide silver halide desensitizer and a piazine having up to 24 carbon atoms and containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically.
  • a photographic silver halide emulsion desensitized to visible radiation with a tetraalkyl thiuram disulfide silver halide desensitizer and a piazine having up to 24 carbon atoms and containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically, the concentration of said thiuram disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • each of R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-merr1- bered carbocyclic ring and each n is an integer of to 2, the concentration of said thiuram disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said thiuram disulfide to said piazine being in the range of about 2: 1 to about 20: 1.
  • each of R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring
  • R is alkyl, hydroxyalkyl or aryl
  • X is an anion
  • each n is an integer of 0 to 2
  • z is an integer of 0 to 1
  • the concentration of said thiuram disulfide being in the range of about 2 to about mg. per mole of silver halide and the weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • a photographic silver halide emulsion desensitized to visible radiation with bis(dimethy1thiocarbamyl)disulfide and 1,3-diarnino-5-methyl phenazinium chloride, the concentration of said disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20: l.
  • a photographic silver halide emulsion desensitized to visible radiation with bis(morpholinothio carbarnyl) disulfide and 1,3-diamino-5-methyl phenazinium chloride, the concentration of said disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20: 1.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with a thiuram disulfide silver halide desensitizer and a piazine containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with a thiuram disulfide silver halide desensitizer and a piazine having up to 24 carbon atoms and containing a pyrazine ring to which two 6-rnembered carbocyclic rings are fused symmetrically.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with a thiuram disulfide silver halide desensitizer and a piazine having up to 24 carbon atoms and containing a pyrazine ring to which two G-membered carbocyclic rings are fused symmetrically, the concentration of said thiuram disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with a tetraalkyl thiuram disulfide silver halide desensitizer and a piazine having the formula:
  • each of R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring and each n is an integer of 0 to 2, the concentration of said thiuram disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and Ithe weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with a tetraalkyl thiuram disulfide silver halide desensitizer and a piazine having the formula:
  • R and R is amino, hydroxy, hydocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring
  • R is alkyl, hydroxyalkyl or aryl
  • X is an anion
  • each n is an integer of 0 to 2
  • z is an integer of 0 to 1, the concentration of said thiuram disulfide being in the range of about 2 to about 75 mg.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with -bis(dimethylthio carbamyl) disulfide and l,3-diamino-5-rnethyl phenazinium chloride, the concentration of said disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20:1.
  • a photographic element comprising a support and a photographic silver halide emulsion layer desensitized to visible radiation with bis(morpholinothio carbamyl) disulfide and 1,3-diamino-5-methyl phenazinium chloride, the concentration of said disulfide being in the range of about 2 to about 75 mg. per mole of silver halide and the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20: 1.
  • a photographic silver halide desensitizing combination comprising a thiuram disulfide silver halide desensitizer and a piazine containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically.
  • a photographic silver halide desensitizing combination comprising a thiuram disulfide silver halide desensitizer and a piazine having up to 24 carbon atoms and containing a pyrazine ring to which two 6-membered carbocyclic rings are fused symmetrically, the weight ratio of said thiuram disulfide to said piazine being in the range of about 5:1 to about 10:1.
  • a photographic silver halide desensitizing combination comprising a tetraalkyl thiuram disulfide silver halide desensitizer and a piazine having the formula:
  • each of R and R is amino, hydroxy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring and each n is an integer of 0 to 2, the weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • a photographic silver halide desensitizing combination comprising a tetraalkyl thiuram disulfide silver halide desensitizer and a piazine having the formula:
  • each of R and R is amino, hydroXy, hydrocarbyl amino, alkyl, aryl, acyloxy, acylamino or a fused 6-membered carbocyclic ring
  • -R is alkyl, hydroxyalkyl or aryl
  • X is an anion
  • each m is an integer of 0 to 2
  • z is an integer of 0 to 1
  • the weight ratio of said thiuram disulfide to said piazine being in the range of about 2:1 to about 20:1.
  • a photographic silver halide desensitizing combination comprising bis(dimethylthio carbamyl) disulfide and 1,3-diamino-5-methyl phenazinium chloride, the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20:1.
  • a photographic silver halide desensitizing combination comprising bis (morpholinothio carbamyl) disulfide and 1,3-diamino-5-methyl phenazinium chloride, the weight ratio of said disulfide to said phenazinium chloride being in the range of about 2:1 to about 20:1.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
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  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US482632A 1965-08-25 1965-08-25 Desensitization of silver halides to visible radiation with thiuram disulfides Expired - Lifetime US3403025A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US482632A US3403025A (en) 1965-08-25 1965-08-25 Desensitization of silver halides to visible radiation with thiuram disulfides
FR73401A FR1490050A (fr) 1965-08-25 1966-08-18 Nouvelles émulsions photographiques aux halogénures d'argent désensibilisés au rayonnement visible
BE685779D BE685779A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1965-08-25 1966-08-19
DE19661547727 DE1547727B1 (de) 1965-08-25 1966-08-24 Gegenueber sichtbarem Licht desensibilisierte photographische Silberhalogenidemulsion
GB38128/66A GB1155053A (en) 1965-08-25 1966-08-25 Sensitive Silver Halide Photographic Materials

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US482632A US3403025A (en) 1965-08-25 1965-08-25 Desensitization of silver halides to visible radiation with thiuram disulfides

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DE (1) DE1547727B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3526507A (en) * 1965-04-28 1970-09-01 Keuffel & Esser Co Autopositive reproduction material
US3658547A (en) * 1969-03-07 1972-04-25 Fuji Photo Film Co Ltd Silver halide photographic emulsions containing phenozine-n-oxides desensitizers
US3718469A (en) * 1969-10-17 1973-02-27 Fuji Photo Film Co Ltd Making of a photographic image
US4036650A (en) * 1974-08-27 1977-07-19 Canon Kabushiki Kaisha Heat developable photosensitive material containing compounds of sulfur
US4539291A (en) * 1982-12-24 1985-09-03 Fuji Photo Film Co., Ltd. Direct positive silver halide photographic materials
US5356770A (en) * 1992-05-29 1994-10-18 Eastman Kodak Compamn Color photographic materials and methods with stabilized silver chloride emulsions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL25041C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1927-06-15
GB563691A (en) * 1943-02-22 1944-08-28 Kodak Ltd Improvements relating to phenazinium salts and their use in photographic emulsions and developers

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3526507A (en) * 1965-04-28 1970-09-01 Keuffel & Esser Co Autopositive reproduction material
US3658547A (en) * 1969-03-07 1972-04-25 Fuji Photo Film Co Ltd Silver halide photographic emulsions containing phenozine-n-oxides desensitizers
US3718469A (en) * 1969-10-17 1973-02-27 Fuji Photo Film Co Ltd Making of a photographic image
US4036650A (en) * 1974-08-27 1977-07-19 Canon Kabushiki Kaisha Heat developable photosensitive material containing compounds of sulfur
US4539291A (en) * 1982-12-24 1985-09-03 Fuji Photo Film Co., Ltd. Direct positive silver halide photographic materials
US5356770A (en) * 1992-05-29 1994-10-18 Eastman Kodak Compamn Color photographic materials and methods with stabilized silver chloride emulsions

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DE1547727B1 (de) 1970-10-08
BE685779A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1967-02-01
GB1155053A (en) 1969-06-18

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