US3438777A - Photographic material - Google Patents

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Publication number
US3438777A
US3438777A US615389A US3438777DA US3438777A US 3438777 A US3438777 A US 3438777A US 615389 A US615389 A US 615389A US 3438777D A US3438777D A US 3438777DA US 3438777 A US3438777 A US 3438777A
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Prior art keywords
silver
bis
image
light
sensitive
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US615389A
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Jozef Frans Willems
Antoon Leon Vandenberghe
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Agfa Gevaert NV
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Agfa Gevaert NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
    • G03C1/355—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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/02—Photosensitive materials characterised by the image-forming section
    • G03C8/04—Photosensitive materials characterised by the image-forming section the substances transferred by diffusion consisting of inorganic or organo-metallic compounds derived from photosensitive noble metals
    • G03C8/06—Silver salt diffusion transfer

Definitions

  • the present invention relates to the use of 5,5-bis-1,2,4- triazoline-3-thiones for photographic purposes.
  • the present invention relates to the use of 5,5'-bis-1,2,4-triazoline-3-thiones corresponding to the following general formula or tautomeric forms thereof:
  • A represents a chemical bond or a bivalent organic radical, more particularly a bivalent organic radical derived from an aliphatic dicarboxylic acid or from a dicarboxylic acid of carbocyclic or heterocyclic systems by removal of the carboxyl groups such as alkylene including substituted alkylene, arylene including substituted arylene, aralkylene including substituted aralkylene, cycloalkylene including substituted cycloalkylene or a bivalent heterocyclic radical including a substituted heterocyclic radical, and
  • each of R and R represents hydrogen, alkyl including substituted alkyl, aryl including substituted aryl or a heterocyclic radical including a substituted heterocyclic radical, at least one of R and R being a hydrogen atom, as antibronzing agents i.e. as agents for preventing the images obtained in light-sensitive silver halide emulsion layers of a photographic printing material from being bronzed by hot glazing or mechanical drying at elevated temperature and as anti-sludge agents to prevent the formation of metallic silver deposit in processing solutions for the silver complex diffusion transfer process.
  • antibronzing agents i.e. as agents for preventing the images obtained in light-sensitive silver halide emulsion layers of a photographic printing material from being bronzed by hot glazing or mechanical drying at elevated temperature and as anti-sludge agents to prevent the formation of metallic silver deposit in processing solutions for the silver complex diffusion transfer process.
  • the said antibronzing agents of use according to the invention When incorporating the said antibronzing agents of use according to the invention into the photographic material, they are generally incorporated into the light-sensitive silver halide emulsion printing layer itself. They can be added to the printing silver halide emulsion at any moment during its preparation, but preferably after chemi- 3,438,777; Patented Apr. 15, 1969 cal ripening or just before coating. This addition occurs in general from a solution of the compound in an appropriate solvent such as water, alcohol, dimethylformamide, dioxan and so on. Instead of incorporating the compounds into the light-sensitive silver halide emulsion layer of the photographic printing material they can also be incorporated into at least one additional water-permeable layer coated at the same side of the support as the said emulsion layer. Evidently, mixtures of different compounds according to the above general formula may be used as well.
  • the total concentration of antibronzing agent of use according to the present invention in the light-sensitive printing material may vary within wide limits, but is preferably chosen in such a way that per sq. m. of light-sensitive material from some mg. to approximately 500 mg.
  • Light-sensitive printing material of use according to the present invention may comprise any printing silver halide emulsion layer such as for instance a gelatino silver chloride emulsion layer, a gelatino silver chlorobromide emulsion layer, a gelatin'o silver bromide emulsion layer, a gelatino silver bromoiodide emulsion layer and a gelatino silver chlorobromoiodide emulsion layer.
  • the silver halide emulsion may contain all known additives, such as anti-fogging agents, stabilizers, hardening agents, plasticizers and dispersing agents. Further, the emulsion may be sensitized chemically as well as spectrally.
  • the light-sensitive printing emulsions can also be sensitized by means of reducing agents for instance the tin compounds described in the Belgian patent specifications 493,464 and 568,687, the iminoaminomethane sulphinic acid compounds described in the British patent specification 789,823 or by means of small amounts of noble metal compounds such as gold compounds, platinum compounds, palladium compounds, iridium compounds, ruthenium compounds and rhodium compound-s.
  • polyoxyalkylene derivatives for instance polyoxyethylene of a molecular weight ranging between 1000 and 20,000 or condensation products of alkylene oxides with aliphatic alcohols, glycols, cyclic dehydration products of hexitols, alkyl-su'bstituted phenols, aliphatic carboxylic acids, aliphatic amines, aliphatic diamines and aliphati amides.
  • the condensation products have a molecular weight of at least 700, preferably of more than 1000.
  • these sensitizers can be applied in combination as described in the Belgian patent specification 537,278 and in the British patent specification 727,982.
  • anti-bronzing compounds of use according to the invention can be incorporated into the said material prior to hot-glazing or drying at elevated temperature by dissolving them in any processing bath such as the developing bath, the fixing bath, an additional hardening bath, and a bath, which contains surface-active compounds and which is used as a last treating bath before hot-glazing or before drying at elevated temperature of the image-containing material.
  • the photographic printing material When the photographic printing material is led through such a bath, it absorbs a certain amount of the said antibronzing agent into its waiter-permeable layers, which assures the retaining of the density of the silver-containing image during hot-glazing or drying at high temperature as successfully as in the case the anti-bronzing agent is present in the light-sensitive material from its preparation on.
  • said material can be treated prior to hot-glazing or drying at elevated temperature with a bath containing a mere solution of said anti-bronzing agents.
  • the anti-bronzing agents of use according to the invention are dissolved in one of the above baths, they are mostly dissolved in the form of their alkali salts in concentrations which can vary within very wide limits preferably, however, between approximately 50 mg. and approximately 3 g./litre.
  • the compounds corresponding to the above general formula or a tautomeric form thereof must not necessarily be present in the processing solution itself but may also be incorporated into at least one waterpermeable layer of the image-receiving material.
  • the image-receiving material which can be used in a silver complex diffusion transfer process wherein the 5,5'-bis-1,2,4-triazoline-3-thiones or tautomeric forms thereof are used as anti-sludge agents, mostly consists of a support e.g. of paper which carries one or more layers, one of which is the image-receiving layer or nuclei-containing layer wherein the diffusion transfer image is formed in the presence of developing nuclei (physical and/or chemical) and/or of substances which are capable of forming developing nuclei with the diffusing complexed silver halide.
  • the image-receiving material can also consist of a mere paper support incorporating constituents such as developing nuclei.
  • an image-receiving material can be used which is composed in such a way that several positive copies of an original can be produced from only one imagewise exposed light-sensitive material.
  • Such an image-receiving material is among others described in the British patent specifications 950,960 and 961,177.
  • the image-receiving layer can also be applied to the same support as the silver halide emulsion layer.
  • the image-receiving layer is mostly coated onto a support e.g. of paper and covered with a non-hardened or slightly hardened light-sensitive silver halide emulsion layer.
  • a support e.g. of paper
  • a non-hardened or slightly hardened light-sensitive silver halide emulsion layer is described among others in the British patent specification 654,631.
  • the exposed and developed unhardened emulsion layer can be removed e.g. by washing away with warm water or by stripping after having been in contact with a sheet of common paper.
  • a separating layer Between the image-receiving layer and the light-sensitive layer there can also be present a separating layer.
  • a starch ether separating layer which enables the detaching of the light-sensitive layer as a coherent sheet, by simply bringing the multilayer material into an aqueous rinsing bath after the diffusion transfer image formation.
  • the light-sensitive material suitable for a diffusion transfer process wherein anti-sludge agents as described above can be used may be any light-sensitive silver halide material the exposed silver halide of which is sufficiently rapidly developed and the non-exposed silver halide is sufiiciently rapidly complexed for allowing the formation of a diffusion transfer image to take place.
  • silver chloride emulsions are used which may contain specific amounts of silver bromide or silver iodide or which some ingredients may be added in order to obtain the desired emulsion characteristics.
  • the developing substance(s) can be incorporated into the light-sensitive material and/or into the bath and/or into the image-receiving material.
  • Suitable developing substances are among others: hydroquinone, monomethylp-aminophenol sulphate, aminophenol and 3-pyrazolidinone developing substances.
  • hydroquinone together with a bisulphite can be present in the image-receiving material, as described in the British patent specification No. 1,000,115.
  • combinations of two or more developing agents can be used successfully, such as the combination of hydroquinone and a 3-pyrazolidinone derivative together in the image-receiving material as described in the British patent application No.
  • the complexing agent forming a soluble complex with the silver halides is preferably an alkali thiosulphate and can be incorporated into the image-receiving material as well as into the processing bath.
  • Sulphides of heavy metals such as of antimony, bismuth, cadmium, cobalt, lead, nickel and silver; heavy metals such as silver, gold, platinum, palladium and mercury, preferably in their colloidal form, and/or other substances which can serve as developing nuclei for the complexed silver halide are mostly incorporated into the image-receiving layer. However, they can also be present in the processing bath. In the latter case, use is made of a light-sensitive and image-receiving material with a specific composition. Such diffusion-transfer process with developing nuclei and/or compounds capable of forming such nuclei present in the processing bath has among others been described in the British patent specification No. 1,001,558 and in the British patent application Ser. No. 1,052,022.
  • This fog-inhibiting agent e.g., can be present in the light-sensitive silver halide material and/ or in the processing bath.
  • the amount of 5,5'-bis-1,2,4-triazoline-3-thione corresponding to the above general formula or a tautomeric form thereof, used for preventing the formation of metallic silver deposit in silver complex diffusion transfer processing liquids may vary within wide limits say from about 0.1 g. to about 3 g. per litre, when incorporated in the developing solution and from about 1 mg. to about 20 mg. per sq. m. when applied in an image-receiving material for use in the silver complex diffusion transfer process.
  • the 5,5-bis-1,2,4-triazoline-3-thiones corresponding to the above general formula or tautomeric forms thereof, which are suitable for use as anti-bronzing agents in lightsensitive printing material or in at least one of the processing solutions for such material and for use as antisludge agents in the silver complex diifusion transfer process, can be prepared by cyclisation of thiosemicarbazide, 4-substituted thiosemicarbazide or 2-substituted thiosemicarbazide, e.g., 4-methyl-thiosemicarbazide, 4-phenyl-thiosemicarbazide, 4-(p-chlorophenyl)-thiosemicarbazide, 4- (p-ethoxyphenyl)-thiosemicarbazide, 4-a-pyridylthiosemicarbazide, 2-methyl-thiosemicarbazide, and so on, with dicarboxylic acid esters in an alcoholate medium analogously to
  • the dicarboxylic acid ester is an ester of an aliphatic unsaturated dicarboxylic acid
  • the resulting 5,5-bis- 1,2,4-triazoline-3-thione will show no double bond(s) any more owing to the addition of an alkoxy group or groups, which group(s) depend on the alcoholate medium applied.
  • dicarboxylic acid esters may be used esters of aliphatic dicarboxylic acids and of dicarboxylic acids of carbocyclic and heterocyclic systems.
  • suitable esters are the esters of oxalic acid, malonic acid, methyl and ethyl malonic acid, succinic acid, glutaric acid, adipic acid, sebacic acid, tartaric acid, fumaric acid, maleic acid, terephthalic acid, isophthalic acid, 2,6-naphthalene dicarboxylic acid, 1,4-dicarboxycyclohexane, 2- carboxy-2-methyl-cyclohexane acetic acid, 3,5-dicarboxypyridine, 3-carboxy-cinnarnic acid, and so on.
  • esters it appears to be of no importance what kind of ester is used since it has been experienced that the yields are practically the same whatever esters are used say the methyl esters, the ethyl esters, the isopropyl esters or the t-butylesters.
  • EXAMPLE 1 Material 1 Materials 2-14 These materials are prepared in the same way as material 1 with the difference however that. per kg. of lightsensitive emulsion ready for coating, the compounds listed in the table hereinafter are added in the amounts given from an aqueous alkaline solution.
  • the 14 material strips are rinsed for a moment and then fixed for five minutes at room temperature in the following composition:
  • the 14 material strips are finally pressed for 6 minutes with their image-containing side against a polished plate of 80 C.
  • EXAMPLE 2 Material 1 Materials 2-14 These materials are prepared in the same way as material 1 with the difference however that per kg. of lightsensitive emulsion ready for coating, the compounds listed in the table of Example 1 are added in the amounts given.
  • EXAMPLE 3 Material 1 Materials 2-14 These materials are prepared in the same way as material 1 with the difference however that per kg. of lightsensitive emulsion ready for coating, the compounds listed in the table of Example 1 are added in the amounts given.
  • a black sludge begins to deposit when about 60 silver complex diffusion transfer copies are produced. This sludge formation increases with the number of diffusion transfer copies made. The diffusion transfer copies obtained with the aid of a developing bath containing said sludge show black spots.
  • EXAMPLE 5 An image-receiving material is prepared by coating a 90 g./ sq. m. paper support in a ratio of 20 sq. m./litre with a layer from a suspension of the following composition:
  • Sandozol (trade name for a sulphonated organic oil marketed by Sandoz A.G., Basel, Switzerland) ccs 1 Water, to 1000 ccs.
  • a gelatino silver chloride emulsion paper containing per sq. m. an amount of silver chloride equivalent to 1.35 g. of silver nitrate is exposed while being in contact with an original to be reproduced, whereupon it is led together with the above mentioned image-receiving material through a developing bath of the composition given in Example 4.
  • an image-receiving material having the same composition as the one above but comprising in addition thereto per sq. m. 4 mg. of bis(3- thioxo-l,2,4-triazolin-5-yl)-methane the developing bath remains clear and can be used until exhaustion without silver sludge being formed. 7
  • a light-sensitive material is prepared by coating a paper support of 90 g./ sq. m. with a gelatino silver chloride emulsion containing l-phenyl-3-pyrazolidinone and hydroquinone in such a way that per sq. m. an amount of silver chloride equivalent to 0.8 g. silver nitrate, 0.5 g. of 1-phenyl-3-pyrazolidinone and 1 g. of hydroquinone are present.
  • the light-sensitive silver chloride emulsion layer is then overcoated with a hydroxyethyl cellulose layer pro rata of 0.5 g./ sq. 111.
  • An image-receiving material is prepared by coating onto a paper support of 90 g./sq. m. a thin layer from a suspension of the following composition pro rata of 1 litre per 30 sq. m.: I
  • the light-sensitive material is now image-wise exposed and together with the image-receiving: material passed through a common diffusion transfer developing apparatus containing a processing solution of the following composition:
  • Example 6 is repeated with the difference however that the processing solution comprises no 1,3-bis(3-thioxo-1,2, 4-triazolin-5-yl)-propane and that to the suspension from which the image-receiving layer is coated an amount of 1,3-bis(3-thioxo-1,2,4-triaZolin-5-yl)-propane is added in such a way that after drying 4 mg. of said compound are present per sq. m.
  • Photographic printing material comprising a support and at least one light-sensitive silver halide emulsion layer, wherein the light-sensitive silver halide emulsion layer and/or at least one water-permeable layer coated at the same side of the support as the said emulsion layer contains at least one 5,5'-bis-1,2,4-triazoline-3-thione corresponding to the following general formula or tautomeric form thereof:
  • each of R and R is hydrogen, an alkyl group, an aryl group or a heterocyclic group, at least one of R and R being hydrogen, and
  • A is a chemical bond or an organic bivalent radical
  • Photographic printing material wherein said organic bivalent radical is an alkylene radical, an arylene radical, an aralkylene radical, a cycloalkylene radical or a bivalent heterocyclic radical.
  • Photographic printing material comprising a support and at least one light-sensitive silver halide emulsion layer, wherein the light-sensitive silver halide emulsion layer and/or at least one water-permeable layer coated at the same side of the support as the said emulsion layer contains at least one cyclisation product of thiosemicarbazide, Z-substituted thiosemicarbazide or 4-substituted thiosemicarbazide with an ester of an aliphatic dicarboxylic acid, a dicarboxylic acid of a carbocyclic system or a dicarboxylic acid of a heterocyclic system.
  • Photographic processing bath contain at least one 5,5'-bis-1,2,4-triazoline-3-thione corresponding to the following general formula or tautomeric form thereof:
  • each of R and R is hydrogen, an alkyl group, an aryl group or a heterocyclic group, at least one of R and R being hydrogen, and
  • A is a chemical bond or an organic bivalent radical, derived from an aliphatic dicarboxylic acid or a dicarboxylic acid of a carbocyclic or a heterocyclic system by removal of the carboxyl groups.
  • each of R and R is hydrogen, an alkyl group, an aryl group or a heterocyclic group, at least one of R and R being hydrogen, and
  • A is a chemcial bond or an organic bivalent radical
  • Photographic silver complex diffusion transfer process according to which a positive image of an original is obtained by development of an image-wise exposed light-sensitive silver halide emulsion layer and diifusion of the non-developed complexed silver halide from the emulsion layer to an image-receiving material where the complexed silver halide is converted into a silvercontaining image in the presence of development nuclei or substances capable of forming such nuclei, wherein said process is carried out in the presence of at least one 5,5'-bis-1,2,4-triazoline-3-thione corresponding to the following general formula or tautomeric form thereof:
  • each of R and R is hydrogen, an alkyl group, an aryl group or a heterocyclic group, at least one of R and R being hydrogen, and
  • each of R and R is hydrogen, an alkyl group, an aryl group or a heterocyclic group, at least one of R and R being hydrogen, and
  • A is a chemical bond or an organic bivalent radical, derived from an aliphatic dicarboxylic acid or a dicarboxylic acid of a carbocyclic or a heterocyclic system by removal of the carboxyl groups.
  • Processing bath according to claim 4 for use in a silver complex diffusion transfer process.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US615389A 1966-02-14 1967-02-13 Photographic material Expired - Lifetime US3438777A (en)

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Application Number Priority Date Filing Date Title
GB6332/66A GB1138587A (en) 1966-02-14 1966-02-14 Improvements in or relating to photographic material

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BE (1) BE694030A (is")
DE (1) DE1522425A1 (is")
FR (1) FR1511336A (is")
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NL (1) NL6702133A (is")

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3647451A (en) * 1968-03-28 1972-03-07 Agfa Gevaert Ag Antibronzing agents for photographic silver images
US3718468A (en) * 1969-04-15 1973-02-27 Agfa Gevaert Ag Stabilising developed photographic images
DE2803199A1 (de) * 1977-02-01 1978-08-03 Konishiroku Photo Ind Verfahren zur herstellung hochkontrastreicher silberbilder
DE2711942A1 (de) * 1977-03-18 1978-09-21 Agfa Gevaert Ag Photographisches material mit verbesserten eigenschaften
US5187054A (en) * 1991-06-24 1993-02-16 Agfa-Gevaert N.V. Anti-sludging compounds in photographic material
CN106397345A (zh) * 2016-09-12 2017-02-15 广西师范大学 一种3‑羧基‑1，2，4‑三氮唑类钴配合物及其原位合成方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573027A (en) * 1944-11-13 1951-10-30 Ilford Ltd Photographic element and process utilizing antibronzing agents
US2590775A (en) * 1949-04-11 1952-03-25 Ilford Ltd Silver halide emulsion containing a thio-imino-urazole as a stabilizer
US3068098A (en) * 1960-03-23 1962-12-11 Eastman Kodak Co Photographic diffusion transfer process
US3359106A (en) * 1963-03-29 1967-12-19 Gevaert Photo Prod Nv Photographic material

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2573027A (en) * 1944-11-13 1951-10-30 Ilford Ltd Photographic element and process utilizing antibronzing agents
US2590775A (en) * 1949-04-11 1952-03-25 Ilford Ltd Silver halide emulsion containing a thio-imino-urazole as a stabilizer
US3068098A (en) * 1960-03-23 1962-12-11 Eastman Kodak Co Photographic diffusion transfer process
US3359106A (en) * 1963-03-29 1967-12-19 Gevaert Photo Prod Nv Photographic material

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3647451A (en) * 1968-03-28 1972-03-07 Agfa Gevaert Ag Antibronzing agents for photographic silver images
US3718468A (en) * 1969-04-15 1973-02-27 Agfa Gevaert Ag Stabilising developed photographic images
DE2803199A1 (de) * 1977-02-01 1978-08-03 Konishiroku Photo Ind Verfahren zur herstellung hochkontrastreicher silberbilder
DE2711942A1 (de) * 1977-03-18 1978-09-21 Agfa Gevaert Ag Photographisches material mit verbesserten eigenschaften
US5187054A (en) * 1991-06-24 1993-02-16 Agfa-Gevaert N.V. Anti-sludging compounds in photographic material
CN106397345A (zh) * 2016-09-12 2017-02-15 广西师范大学 一种3‑羧基‑1，2，4‑三氮唑类钴配合物及其原位合成方法
CN106397345B (zh) * 2016-09-12 2019-02-19 广西师范大学 一种3-羧基-1，2，4-三氮唑类钴配合物及其原位合成方法

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FR1511336A (fr) 1968-01-26
DE1522425A1 (de) 1969-07-31
GB1138587A (en) 1969-01-01
BE694030A (is") 1967-08-14
NL6702133A (is") 1967-04-25

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