EP0624821B1 - Comprimé pour le traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière - Google Patents

Comprimé pour le traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière Download PDF

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Publication number
EP0624821B1
EP0624821B1 EP19940106615 EP94106615A EP0624821B1 EP 0624821 B1 EP0624821 B1 EP 0624821B1 EP 19940106615 EP19940106615 EP 19940106615 EP 94106615 A EP94106615 A EP 94106615A EP 0624821 B1 EP0624821 B1 EP 0624821B1
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Prior art keywords
group
tablet
acid
represent
salt
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EP19940106615
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German (de)
English (en)
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EP0624821A1 (fr
Inventor
Ichiro Tsuchiya
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Konica Minolta Inc
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Konica Minolta Inc
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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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/264—Supplying of photographic processing chemicals; Preparation or packaging thereof
    • G03C5/265—Supplying of photographic processing chemicals; Preparation or packaging thereof of powders, granulates, tablets

Definitions

  • the present invention relates to a tablet for processing a silver halide color photographic light-sensitive material, and more particularly relates to a tablet for preparing a processing solution of a silver halide color photographic light-sensitive material having sufficient strength and excellent storage stability.
  • a silver halide photographic light-sensitive material after being exposed is photographically processed through a development step, a desalting step, a washing step and a stabilization step.
  • the photographic processing is ordinarily conducted using an automatic processing machine.
  • a replenisher replenishing system is commonly used wherein the processing solution in a processing tank is controlled so that the degree of activity thereof is kept constant.
  • the purposes thereof include dilution of materials dissolved from the light-sensitive material, and replenishment of consumed components, usually resulting in an occurrence of a large amount of an over flowing waste solution and an empty vessel.
  • Japanese Patent O.P.I. Publication No. 119454/1993 discloses a method to make up almost all processing components into a solid processing agent and to charge it to a processing tank directly.
  • the temperature extremes between day and night during the transportation may reach 15 to 20 °C, and the humidity may vary by 20 to 30 %RH. Accordingly, in such cases, the above-mentioned problem becomes more apparent.
  • EP-A-0 542 283 discloses a tablet for processing a silver halide photographic light sensitive material which tablet is prepared by stacking two or more granules or powders differing in composition (eg. a thiosulfate at the one hand and a Fe complex salt at the other hand) optionally with a polymer (photographically inactive substance) inserted inbetween in a layered construction and thereafter applying pressure onto said granules or powders in the layered structure.
  • composition eg. a thiosulfate at the one hand and a Fe complex salt at the other hand
  • a polymer photographically inactive substance
  • EP-A-0 542 283 has to be considered as state of the art according to Art. 54(3) EPC and is excluded from the scope of the present invention.
  • An object of the invention is to provide a photographic solid processing tablet for fix-bleach having excellent storage stability and handling property.
  • a solid processing tablet for processing a silver halide color photographic light-sensitive material wherein the tablet comprises at least one thiosulfate salt, at least one ferric complex salt of an amino polycarboxylic acid and at least one compound selected from the group consisting of polyethylene glycols, polyvinylpyrrolidones and polyvinyl alcohols or a method for preparing a solid photographic processing tablet comprising a thiosulfate salt, a ferric complex salt of an amino polycarboxylic acid and a polymer selected from the group consisting of polyethylene glycols, polyvinylpyrrolidones and polyvinyl alcohols, comprising the steps of:
  • the invention is furthermore concerned with a solid photographic processing tablet as disclosed in claim 1.
  • Layered tablets as described in EP-A-0 542 283 are excluded from the scope of claim 1.
  • the tablet of the present invention is characterized by containing, in addition to a thiosulfate and an amino polycarboxylic acid ferric complex salt, at least one kind selected from polyethylene glycols, polyvinyl pyrrolidones and polyvinyl alcohols.
  • a thiosulfate and an amino polycarboxylic acid ferric complex salt at least one kind selected from polyethylene glycols, polyvinyl pyrrolidones and polyvinyl alcohols.
  • the average molecular weight by weight of the polyvinyl alcohols is preferably 2000 to 200,000 and more preferably 3000 to 100,000.
  • the average molecular weight by viscosity of the polyvinyl pyrrolidones of the present invention is preferably 10000 to 700,000.
  • polyethylene glycols provide the effects of the present invention most noticeably.
  • the polymer of the present invention is preferably contained by 10 to 50 wt % in one tablet from the viewpoint of the effects of the present invention and the strength of the tablet.
  • the solid processing tablet of the invention preferably contains a saccharide in enhancing the tablet strength as well as preventing an unfavorable reaction inside the tablet during its long storage period.
  • the saccharide preferably includes an saccharide alkohol such as mannitol, sorbitol or erythritol, or a dextrin such as maltodextrin or cyclodextrin.
  • the solid processing agent of the present invention is a tablet agent.
  • a powder agent and a granulated processing agent are not included in the present invention.
  • the tablet of the invention is obtained by compressin molding powder and/or granule. It is preferred in terms of the effects of the invention that granules containing ferric complex salt of poly aminocarboxylic acid and granules containing a thiosulfate are mixed, followed by compresion molding the resulting mixture.
  • a granulating method for forming a tablet agent conventional methods such as a rotation granulation method, a extruding granulation method, a compression granulation method and a fluid layer granulation method can be used.
  • the average particle diameter of the resulting granules is preferably 100 to 1500 ⁇ m in terms of the effects of the present invention, and more preferably 300 to 1000 ⁇ m.
  • the tablet of the present invention can be produced by a conventional compressor, for example, an oil-pressure pressor, single-type tableting device, a rotary type tableting device and a briqueting machine.
  • the tablet of the invention may be in any solid form, according to the method for use, for example, in the form of a circular cylinder, an elliptic cylinder, a triangle prism, a square prism, a regular polygonal prism or an ovoid.
  • the tablet is preferably in the form of a circular cylinder, an elliptic cylinder or a regular polygonal prism from the viewpoint of its strength and productivity, and more preferably in the form of a circular cylinder.
  • the tablet of the invention is most preferably in the form of a disk in which the diameter x and the thickness h preferably has the following relationship: 1.0 ⁇ x/h ⁇ 6.0
  • the diameter is preferably 5 to 50 mm, and more preferably 7 to 30 mm.
  • the tablet in the form of a disk may have protrusions and cavities on its surface.
  • the thiosulfate of the invention is preferably ammonium thiosulfate or an alkali metal thiosulfate.
  • the alkali metal is preferably sodium or potassium in terms of processability of the tablet.
  • the thiosulfate content of the tablet of the is prefarably 20 to 70 % by weight, and more preferably 30 to 60 % by weight per tablet.
  • the ferric complex salt used in the processing tablet of the invention includes those of a compound represented by the following Formula (A-I), (A-II), (A-III), or (A-IV): wherein A 1 to A 4 may be the same with or the different from each other and represent each a hydrogen atom, a hydroxy group, -COOM, -PO 3 (M 1 ) 2 , -CH 2 COOM 2 , -CH 2 OH or a lower alkyl group, provided that at least one of A 1 to A 4 represents -COOM, -PO 3 (M 1 ) 2 or -CH 2 COOM 2 ; and M, M 1 and M 2 represent each a hydrogen atom, an ammonium group, an alkali metal or an organic ammonium group.
  • a 1 to A 4 may be the same with or the different from each other and represent each a hydrogen atom, a hydroxy group, -COOM, -PO 3 (M 1 ) 2 , -CH 2 COOM 2 , -
  • a 11 to A 14 may be the same with or the different from each other and represent each -CH 2 OH, -COOM 3 or -PO 3 (M 4 ) 2 ;
  • M 3 and M 4 represent each a hydrogen atom, an ammonium group, an alkali metal or an organic ammonium group;
  • X represents an alkylene group having 2 to 6 carbon atoms or -(B 1 O) n -B 2 - in which n is an integer of 1 to 8 and B 1 and B 2 may be the same with or the different from each other and represent each an alkylene group having 1 to 5 carbon atoms.
  • the alkylene groups represented by X include, for example, the groups of ethylene, propylene or butylene.
  • the alkylene groups represented by B 1 and B 2 include, for example, methylene, ethylene and trimethylene. These alkylene groups may also have a substituent including, for example, a lower alkyl group such as a methyl group, an ethyl group, or a hydroxy group.
  • R 1 to R 3 represent each a hydrogen atom, a substituted or unsubstituted alkyl or aryl group
  • L represents either one of the following formulas, or wherein Y 1 to Y 3 represent each an alkylene or arylene group
  • X 2 and X 3 represent each an oxygen atom or a sulfur atom
  • R 4 to R 8 represent each a hydrogen atom, an alkyl group or an aryl group
  • W represents a divalent linking group.
  • the alkyl groups represented by R 1 through R 3 include, for example, those of the straight-chained, the branched and the cyclic, each having 1 to 10 carbon atoms and, among them, a methyl group and an ethyl group are particularly desirable.
  • the aryl groups represented by R 1 through R 3 include, preferably, a phenyl group. When R 1 through R 3 represent each an alkyl or aryl group, each of these groups may have a substituent.
  • R 1 through R 3 include, for example, an alkyl group, an aralkyl group, an alkenyl group, an alkinyl group, an alkoxy group, an aryl group, a substituted amino group, an acylamino group, a sulfonylamino group, a ureido group, a urethane group, an aryloxy group, a sulfamoyl group, a carbamoyl group, an alkylthio group, an arylthio group, a sulfonyl group, a sulfinyl group, a hydroxy group, a halogen atom, a cyano group, a sulfo group, a carboxy group, a phosphono group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an acyloxy group, a carbonamido group, a sul
  • the alkylene groups represented by Y 1 through Y 3 include, for example, a methylene group, an ethylene group or a propylene group.
  • the arylene groups represented thereby include, for example, a phenylene group.
  • Each of the alkylene groups and arylene groups represented by Y 1 through Y 3 may have each a substituent.
  • the substituents applicable thereto include, for example, those given for the substituents of R 1 through R 3 and, among these substituents, the following substituents are preferable.
  • the divalent linking groups represented by W include, desirably, an alkylene group having 2 to 8 carbon atoms (including a cyclohexylene group), an arylene group having 6 to 10 carbon atoms, wherein B 1 and B 2 represent each an alkylene or arylene group and n is an integer of 1 to 3.
  • Z represents a hydrogen atom, an unsubstituted alkyl or aryl group, or an alkyl or aryl group substituted with -COOM, -SO 3 M or -OH; and M represents a hydrogen atom, an alkali metal or an ammonium group.
  • the preferable ones include the compounds represented by the following Formula (B-I) or (B-II).
  • R 1 and R 2 represent each a hydrogen atom, an alkyl group or an aryl group
  • L 1 through L 4 represent each an alkylene group or an arylene group
  • M 1 and M 2 represent each a hydrogen atom, an alkali metal, an ammonium group or an organic ammonium group.
  • R 1 through R 4 are each synonymous with R 1 and R 2 each denoted in Formula (B-I)
  • L 1 through L 4 and M 1 and M 2 are each synonymous with those denoted in Formula (B-II).
  • R 1 to R 3 and R 6 to R 9 represent each a hydrogen atom or a substituted or unsubstituted alkyl or aryl group
  • R 4 and R 5 represent each a hydrogen atom, a halogen atom, a cyano group, a nitro group, an acyl group, a sulfamoyl group, a carbamoyl group, an alkoxycarbonyl group, an allyloxycarbonyl group, a sulfonyl group, a sulfinyl group or a substitutable alkyl or aryl group, provided, R 4 and R 5 may be associated so as to form a 5-membered or 6-membered ring;
  • A represents a carboxy group, a phosphono group, a sulfo group, a hydroxy group or an alkyl metal salt or ammonium salt thereof;
  • Y represents an alkylene group or an arylene group, provided, Y may have a
  • ferric complex salts of the following compounds can be used as bleaching agents for the (hereinafter referred to as)bleacher or bleach-fixer in addition to the ferric complex salts of the above compounds.
  • the content of the compounds represented by the above-given Formulas (A-I) through (A-IV) is preferably 10 to 70 % by weight and more preferably 20 to 60 % by weight per tablet, in view of storage stability.
  • the weight of the tablet agent of the invention is preferred to be 1 to 50 g.
  • a tablet sample was prepared according to the following procedures.
  • Procedure (2) was repeated to obtain granule sample B.
  • Granule sample A in an amount of 3259 g, 3675 g of Granule sample B and 35 g of sodium N-lauroylsarcosine were mixed and the resulting mixture was compression-tabulated in the same manner as in Procedure (3) to obtain 580 pieces of tablet sample A.
  • Table 1 shows the results thereof.
  • Table 1 Sample No. Polymer:12wt% Adhesiveness Degree of abrasion 1-1 PEG 600 B 0.52 Invention 1-2 PEG 1000 B 0.50 Invention 1-3 PEG 4000 A 0.53 Invention 1-4 PEG 6000 A 0.55 Invention 1-5 PEG 10000 A 0.56 Invention 1-6 PEG 2000 A 0.51 Invention 1-7 PVA-1 B 0.95 Invention 1-8 PVA-2 B 0.96 Invention 1-9 PVA-3 B 0.91 Invention 1-10 PVP-1 B 0.83 Invention 1-11 PVP-2 B 0.81 Invention 1-12 PVP-3 B 0.85 Invention 1-13 - D 1.14 Comparative
  • Ammonium thiosulfate of 8000.0 g, 3000 g of sodium metabisulfite were pulverized and 400.0 g of Pineflow was added thereto and mixed in the same manner as in Procedure (7), and the mixture was granulated by adding 170 ml of water thereto. Thereafter, the granules were dried at 60°C for 2 hours to completely remove the moisture and to obtain granules.
  • Polyethylene glycol #4000 (produced by Nihonyushi co. Ltd.) was added in an amount as shown in Table 2 to a mixture of granules obtained in Procedures (7) and (8) and mixed for 10 minutes using Cross-rotary mixer available on the market, and 90.0 g of sodium N-lauroylsarcosine was added thereto and mixed for 3 minutes to obtain mixed granules. Thereafter, the resulting granules was tabletted using a rotary tabletting machine to obtain a tablet having a diameter of 30 mm and a weight of 11.0 g. Thus, 1700 tablets were prepared for each of tablet sample Nos.A-l through A-10.
  • Abrasion degree (wt%) (the difference between the weight of ten tablets before and after the vibration test) ⁇ 100/(the weight of ten tablets before the vibration test)
  • Adhesion of components to be tabletted on the surface of a compression-molding device on tabletting was evaluated.
  • tablets containing the polymer of the invention in an amount of 10 to 50 wt% improve tabletting property, i.e., tablets productivity as well as the adhesiveness or strength of the tablets even in a long storage period.
  • the above effects of the invention was more remarkable in tablets prepared by a method comprising the steps of preparing granules containing ferric complex salt of amino polycarboxylic acid and granules containing a thiosulfate separately, and mixing the resulting granules, followed by tabletting.
  • Tablet samples were prepared in the same manner as in Sample A-5 of Example 2, except that ferric complex salt of exemplified compound A-I-2, A-II-1, A-III-3, or A-IV-1 was used instead of sodium ferric ethylene diamine tetraacetic acid trihydrate.
  • the thus obtained tablets were processed and evaluated in the same manner as in Example 1. The results were the same as those of Example 1.
  • Tablet samples were prepared in the same manner as in Sample A-5 of Example 2, except that sodium thiosulfate or potassium thiosulfate was used instead of ammonium thiosulfate.
  • the thus obtained tablets were processed and evaluated in the same manner as in Example 1. The results were the same as those of Example 1.
  • Tablet samples 4-1 through 4-11 were prepared in the same manner as in Sample A-5 of Example 2, except that the diameter and thickness of the tablet were varied as shown in Table 3. The thus obtained tablets were processed and evaluated in the same manner as in Example 2. The results are shown in Table 3.
  • Table 3 Sample Diameter d (mm) Thickness (mm) d/h Adhesiveness Abrasion proper 4-1 30 4 7.5 B B 4-2 30 5 6.0 A B 4-3 30 10 3.0 A A 4-4 30 20 1.5 A A 4-5 30 30 1.0 A B 4-6 30 35 0.9 B B 4-7 10 4 2.5 A A 4-8 15 5 3.0 A A 4-9 20 5 4.0 A A 4-10 40 10 4.0 A A 4-11 50 10 5.0 A B
  • a tablet sample was prepared according to the following procedures.
  • the hardness of 20 pieces of the tablet samples obtained in accordance with the above-mentioned procedure was measured by means of a tablet hardener (Speed checker produced by Okada Seiko Co., Ltd.) and the average value thereof was calculated.
  • the water-soluble polymer of the present invention provides more desirable results compared to the results of Example 1 when it is incorporated in the granules of an amino polycarboxylic acid ferric salt.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Detergent Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Claims (10)

  1. Comprimé solide pour le traitement photographique, comprenant un sel thiosulfate, un sel complexe ferrique d'un acide aminopolycarboxylique et un polymère choisi dans l'ensemble constitué par les polyéthylèneglycols, les polyvinylpyrrolidones et les poly(alcools vinyliques), à l'exception d'un comprimé ayant une structure lamellaires dont les couches ont des compositions différentes.
  2. Comprimé selon la revendication 1, dans lequel la teneur en polymère du comprimé est comprise entre 10 et 50 % en poids.
  3. Comprimé selon la revendication 1, dans lequel la teneur en thiosulfate du comprimé est comprise entre 20 et 70 % en poids.
  4. Comprimé selon la revendication 1, dans lequel la teneur en sel ferrique du comprimé est comprise entre 10 et 70 % en poids.
  5. Comprimé selon la revendication 1, dans lequel ledit polymère est un polyéthylèneglycol.
  6. Comprimé selon la revendication 1, dans lequel ledit acide aminopolycarboxylique est choisi dans l'ensemble constitué par les composés représentés par les formules suivantes (A II), (A II), (A III) et (A IV) et les composés suivants A'-1 à A'-18 :
    Figure imgb0122
     dans laquelle A1, A2, A3 et A4 représentent chacun un atome d'hydrogène, un groupe hydroxy, -COOM, -PO3(M1)2, -CH2COOM2, -CH2OH ou un groupe alkyle inférieur, du moment qu'au moins l'un de A1 à A4 représente -COOM, -PO3(M1)2 ou -CH2COOM2 ; et M, M1 et M2 représentent chacun un atome d'hydrogène, un groupe ammonium, un métal alcalin ou un groupe ammonium organique ;
    Figure imgb0123
     dans laquelle A11, A12, A13 et représentent chacun -CH2OH, -COOM3 ou -PO3 (M4)2 où M3 et M4 représentent chacun un atome d'hydrogène, un groupe ammonium, un métal alcalin ou un groupe ammonium organique ; et X représente un groupe alkylène ayant de 2 à 6 atomes de carbone ou -(B1O)n-B2- où B1 et B2 représentent chacun un croupe alkylène ayant de 1 à 5 atomes de carbone et n est un entier compris entre 1 et 8 ;
    Figure imgb0124
     dans laquelle R1, R2 et R3 représentent chacun un atome d'hydrogène ou un groupe aryle ou alkyle éventuellement substitué ; L est représenté par l'une des formules suivantes :
    Figure imgb0125
    Figure imgb0126
     ou
    Figure imgb0127
     dans lesquelles Y1, Y2 en Y3 représentent chacun un groupe alkylène ou arylène, X2 et X3 représentent chacun un atome d'oxygène ou un atome de soufre, et R4, R5, R6, R7 et R8 représentent chacun un atome d'hydrogène, un groupe alkyle ou un groupe aryle ; et W représente un groupe de liaison divalent ;
    Figure imgb0128
     dans laquelle R1, R2, R3, R6, R7, R8 et R9 représentent chacun un atome d'hydrogène ou un groupe aryle ou alkyle éventuellement substitué ; R4 et R5 représentent chacun un atome d'hydrogène, un atome d'halogène, un groupe cyano, un groupe nitro, un groupe acyle, un groupe sulfamoyle, un groupe carbamoyle, un groupe alcoxycarbonyle, un groupe allyloxycarbonyle, un groupe sulfonyle, un groupe sulfinyle ou un groupe aryle ou alkyle éventuellement substitué, du moment que R4 et R5 peuvent se combiner pour former un cycle à 5 chaînons ou à 6 chaînons ; A représente un groupe carboxy, un groupe phosphono, un groupe sulfo, un groupe hydroxy ou un sel de métal alcalin ou un sel d'ammonium de celui-ci ; Y représente un groupe alkylène ou un groupe arylène ; et t et u sont chacun un entier valant O ou 1 ;
    A'-1 : acide éthylènediaminetétraacétique
    A'-2 : acide trans-1,2-cyclohexanediaminetétraacétique
    A'-3 : acide dihydroxyéthylglycinique
    A'-4 : acide éthylènediaminetétrakisméthylènephosphonique
    A'-5 : acide nitrilotrisméthylènephosphonique
    A'-6 : acide diéthylènetriaminepentakisméthylènephosphonique
    A'-7 ; acide diéthylènetriaminepentaacétique
    A'-8 : acide éthylènediaminediorthohydroxyphénylacétique
    A'-9 : acide hydroxyéthyléthylènediaminetriacétique
    A'-10 : acide éthylènediaminedipropionique
    A'-11 : acide éthylènediaminediacétique
    A'-12 : acide hydroxyéthyliminodiacétique
    A'-13 : acide nitrilotriacétique
    A'-14 : acide nitrilotripropionique
    A'-15 : acide triéthylènetétraminehexaacétique
    A'-16 : acide éthylènediaminetétrapropionique
    A'-17 : acide 1,3-propylènediaminetétraacétique
    A'-18 : acide glycolétherdiaminetétraacétique
  7. Procédé pour préparer un comprimé solide pour le traitement photographique comprenant un sel thiosulfate, un sel complexe ferrique d'un acide aminopolycarboxylique et un polymère choisi dans l'ensemble constitué par les polyéthylèneglycols, les polyvinylpyrrolidones et les poly(alcools vinyliques),
       comprenant les étapes consistant à :
    granuler une première composition comprenant le sel complexe ferrique ;
    granuler une deuxième composition comprenant le sel thiosulfate ;
    mélanger les produits de granulation résultants avec le polymère ; et
    mouler le mélange résultant par application d'une pression afin d'obtenir un comprimé.
  8. Procédé selon la revendication 7, dans lequel la teneur en polymère du comprimé est comprise entre 10 et 50 % en poids.
  9. Procédé pour préparer un comprimé solide pour le traitement photographique comprenant un sel thiosulfate, un sel complexe ferrique d'un acide aminopolycarboxylique et un polymère choisi dans l'ensemble constitué par les polyéthylèneglycols, les polyvinylpyrrolidones et les poly(alcools vinyliques),
    comprenant les étapes consistant à :
    granuler une première composition comprenant le sel complexe ferrique et le polymère ;
    granuler une deuxième composition comprenant le sel thiosulfate ;
    mélanger les produits de granulation résultants ; et
    mouler le mélange résultant par application d'une pression afin d'obtenir un comprimé.
  10. Procédé selon la revendication 9, dans lequel la teneur en polymère du comprimé est comprise entre 10 et 50 % en poids.
EP19940106615 1993-05-10 1994-04-27 Comprimé pour le traitement d'un matériau photographique couleur à l'halogénure d'argent sensible à la lumière Expired - Lifetime EP0624821B1 (fr)

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JPH07114151A (ja) * 1993-08-23 1995-05-02 Konica Corp ハロゲン化銀写真感光材料用固体処理剤
US5512424A (en) * 1994-03-18 1996-04-30 Konica Corporation Method for manufacturing tablet processing agent for silver halide photographic light-sensitive materials
EP3022171B1 (fr) 2013-07-16 2017-07-05 Akzo Nobel Chemicals International B.V. Nouveaux sels, cristaux, complexes et dérivés d'acide thréonine diacétique, procédé pour préparer la thréonine diacétique et son utilisation

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US5055384A (en) * 1989-05-10 1991-10-08 Agfa Gevaert Aktiengesellschaft Granulated photographic fixative and its preparation
EP0540990B1 (fr) * 1991-11-06 1998-07-15 Konica Corporation Agent de traitement sous forme de tablette et procédé pour le traitement de matériaux photographiques sensibles à la lumière à l'halogénure d'argent
EP0542283A1 (fr) * 1991-11-12 1993-05-19 Konica Corporation Comprimé pour la traitement d'un matériau photographique à l'halogénure d'argent sensible à la lumière

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