EP0446457B1 - Alkalischer photographischer Schwarzweissentwickler - Google Patents

Alkalischer photographischer Schwarzweissentwickler Download PDF

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Publication number
EP0446457B1
EP0446457B1 EP90124427A EP90124427A EP0446457B1 EP 0446457 B1 EP0446457 B1 EP 0446457B1 EP 90124427 A EP90124427 A EP 90124427A EP 90124427 A EP90124427 A EP 90124427A EP 0446457 B1 EP0446457 B1 EP 0446457B1
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EP
European Patent Office
Prior art keywords
developer
per liter
antifoggant
moles per
alkaline aqueous
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Expired - Lifetime
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EP90124427A
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English (en)
French (fr)
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EP0446457A3 (en
EP0446457A2 (de
Inventor
Carlo Marchesano
Carlo Illuminati
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3M Co
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Minnesota Mining and Manufacturing Co
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Classifications

    • 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
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G03C5/3053—Tensio-active agents or sequestering agents, e.g. water-softening or wetting agents

Definitions

  • the present invention relates to an alkaline black-and-white developer for processing a silver halide photographic material and, more particularly, to an alkaline black-and-white hardening developer for processing a silver halide radiographic material in an automatic processor.
  • the developer provides improved stability and excellent photographic properties.
  • Aqueous black-and white developers used for processing silver halide photographic materials comprise, as main components, hydroquinone and 3-pyrazolidone developing agents, an alkali agent, an organic antifoggant and a sulfite.
  • a problem that is frequently encountered with said hardening developers is the tendency of the developing agent to degrade during storage and use.
  • the higher the amount of the sulfite the longer the useful life of the developer.
  • high concentrations of sulfites in a developer cause a reduced activity and dark deposits in the developer tank.
  • the presence of metal ion traces (such as Fe ++ the developer causes the catalytic oxidation of the sulfites.
  • Sequestering agents such as ethylenediaminetetraacetic acid (EDTA), used to prevent the precipitation of calcium salts in the developers, in the presence of traces of iron ions cause the autoxidation of the hydroquinone developing agent at a higher rate than in the absence of the EDTA.
  • EDTA ethylenediaminetetraacetic acid
  • US Pat. NO. 4,672,025 describes a black-and-white developer comprising hydroquinone, a 3-pyrazolidone developing agent, a dialdehyde hardener, an organic antifoggant and a sequestering agent selected from the group consisting of diethylenetriaminepentaacetic acid (DTPA), triethylenetetraminehexa- acetic acid (TTHA) , 1,3-di-amino-2-propanoltetraacetic acid (DPTA), glycol ether diaminetetraacetic acid, ethylenediaminetetramethylenephosphonic acid (EDTP), aminotrimethylenephosphonic acid and alkali metal salts of said acids.
  • DTPA diethylenetriaminepentaacetic acid
  • TTHA triethylenetetraminehexa- acetic acid
  • DPTA 1,3-di-amino-2-propanoltetraacetic acid
  • EDTP ethylenediaminetetramethylenephosphonic acid
  • European Patent Application No. 286,874 describes the use of a dialkylaminomethane diphosphonic acid sequestering agent (including cyclicaminomethane diphosphonic acids) in aqueous alkaline photographic developers to increase the stability of the developers and inhibit deposit formation.
  • Said developers do not include hardeners and are intended for manual processing, preferably of silver halide color photographic materials.
  • US Pat. No. 4,810,622 describes a black-and-white developer having a pH value of 9.2 to 10 comprising hydroquinone, a 3-pyrazolidone developing agent, a dialdehyde hardener, an organic antifoggant, a chelating agent selected form the group consisting of diethylenetriaminepentaacetic acid (DTPA), triethylenetetramine-hexaacetic acid (TTHA), 1,3-diamino-2-propanoltetraacetic acid (DPTA), ethylenediaminetetramethylenephosphonic acid (EDTP), aminotrimethylenephosphonic acid and alkali metal salts of said acids, a silver halide solvent and a sulfite.
  • DTPA diethylenetriaminepentaacetic acid
  • TTHA triethylenetetramine-hexaacetic acid
  • DPTA 1,3-diamino-2-propanoltetraacetic acid
  • EDTP ethylenediaminet
  • Alkaline aqueous black-and-white photographic developers for processing of silver halide radiographic materials comprise (1) a hydroquinone, (2) a 3-pyrazolidone developing agent, (3) a dialdehyde hardener, (4) antifoggants, (5) a sequestering agent, (6) a sulfite antioxidant, and (7) a buffering agent, wherein said sequestering agent is a cyclicaminomethane diphosphonic acid compound, the molar ratio of the buffering agent to the sulfite antioxidant is at least 0.5:1 and the molar ratio of the sulfite antioxidant to hydroquinone is at least 1.5:1.
  • the antifoggants comprise a combination of a benzotriazole-type antifoggant, an indazole-type antifoggant and a mercaptotetrazole-type antifoggant.
  • the developer is stable over long periods of time and can provide excellent photographic properties when used in automatic processing machines.
  • the developer allows control of the photographic characteristics (fog and gradation) even when used at high temperature for rapid processing.
  • the present invention relates to an alkaline aqueous black-and-white photographic developer, for processing a silver halide photographic material, particularly a silver halide radiographic material, comprising (1) at least one of hydroquinones, (2) at least one of 3-pyrazolidone developing agents,(3) at least one of dialdehyde hardeners, (4) at least one antifoggant, (5) a sequestering agent, (6) a sulfite antioxidant, and (7) a buffering agent, characterized in that said sequestering agent is a cyclicaminomethane diphosphonic acid compound, the molar ratio of the buffering agent to the sulfite antioxidant is at least 0.5:1 and the molar ratio of the sulfite antioxidant to hydroquinone is at least 1.5:1.
  • the present invention relates to an alkaline developer as described above, wherein the antifoggant comprise a combination of a benzotriazole-type antifoggant, an indazole-type antifoggant and a mercaptotetrazole-type antifoggant.
  • cyclicaminomethane diphosphonic acid compounds used in the developer of this invention are those described in the European Patent Application No. 286,874.
  • said cyclicaminomethane diphosphonic acid compounds correspond to the following formula wherein R 1 , R 2 and R 3 , equal or different, each represent a hydrogen atom or a PO 3 M'M" group, wherein M' and M" represent a hydrogen atom, an alkaline metal such as Li, Na or K or a quaternary ammonium group such as ammonium, pyridinium, triethanolammonium or triethylammonium, and Q represents the atoms or chemical bonds necessary to complete a 3- to 6-membered ring such as aziridino, pyrrolidino, imidazolidino, piperidino, isoindolino or morpholino, with the proviso that at least two of R 1 , R 2 and R 3 substituents represent a PO 3 M'M" group.
  • Said sequestering agents can be advantageously used in amounts of about 0.0005 to about 0.5 moles per liter, preferably of about 0.008 to about 0.1 moles per liter of the developer.
  • sequestering agents can be used in combination with other sequestering agents known in the art such as, for example, aminopolycarboxylic acids (ethylenediaminotetraacetic acid, diethylenetriaminepentaacetic acid, nitrilotriacetic acid, diaminopropanoltetraacetic acid, etc.), aminopolyphosphonic acids (methylaminophosphonic acid, phosphonic acids described in Research Disclosure 18837 of December 1979, phosphonic acids described in US Pat. No.
  • aminopolycarboxylic acids ethylenediaminotetraacetic acid, diethylenetriaminepentaacetic acid, nitrilotriacetic acid, diaminopropanoltetraacetic acid, etc.
  • aminopolyphosphonic acids methylaminophosphonic acid, phosphonic acids described in Research Disclosure 18837 of December 1979, phosphonic acids described in US Pat. No.
  • polyphosphate compounds sodium hexametaphosphate, etc.
  • ⁇ -hydroxycarboxylic acid compounds lactic acid, tartaric acid, etc.
  • dicarboxylic acid compounds malonic acid, etc.
  • ⁇ -ketocarboxylic acid compounds pyruvic acid, etc.
  • alkanolamine compounds diethanolamine, etc.
  • the sequestering agents incorporated into the black-and-white hardening developer of the present invention have been found to increase the stability of the developer over a long period of time.
  • the developer composition of a present invention is suitable for obtaining black-and white images upon development of light-exposed silver halide photographic materials, in particular radiographic materials.
  • it comprises a black-and-white developing agent, a dialdehyde hardener, a sulfite antioxidant, an antifoggant agent, buffering agents and alkaline agents.
  • Black-and-white developing agents for use in the present invention include hydroquinone and hydroquinone derivatives (for example t-butylhydroquinone, methylhydroquinone, dimethylhydroquinone, chlorohydroquinone, dichlorohydroquinone, bromohydroquinone, 1,4-dihydronaphthalene, methoxyhydroquinone, ethoxyhydroquinone, hydroquinone monosulfonate, hydroquinone disulfonate, etc.). Hydroquinone, however, is preferred.
  • Said- black-and-white developing agents are generally used in amounts of from 0.075 to 0.75 moles per liter, preferably of from 0.10 to 0.50 moles per liter of developer.
  • Said black-and-white developing agents are used in combination with auxiliary developing agents which show a superadditive developing effect, such as p-aminophenol and p-aminophenol derivatives (such as N-methyl-p-aminophenol and 2,4-diaminophenol) and pyrazolidone compounds (such as 1-phenyl-3-pyrazolidone) and pyrazolidone derivatives (such as 4-methyl-1-phenyl-3-pyrazolidone and 4,4'-dimethyl-1-phenyl-3-pyrazolidone).
  • p-aminophenol and p-aminophenol derivatives such as N-methyl-p-aminophenol and 2,4-diaminophenol
  • pyrazolidone compounds such as 1-phenyl-3-pyrazolidone
  • pyrazolidone derivatives such as 4-methyl-1-phenyl-3-pyrazolidone and 4,4'-dimethyl-1-phenyl-3-pyrazolidone.
  • Said auxiliary developing agents are generally used in amounts of from 0.0003 to 0.15 moles per liter, preferably of form 0.003 to 0.1 moles per liter of developer.
  • Dialdehyde hardeners used in the developer of this invention include, for example, glutaraldehyde, ⁇ -methyl-glutaraldehyde, ⁇ -methylglutaraldehyde, maleic dialdehyde, succinic dialdehyde, methoxysuccininc dialdehyde, ⁇ --methoxy- ⁇ -ethoxyglutaraldehyde, ⁇ -n-butoxyglutaraldehyde, ⁇ , ⁇ -dimethoxysuccinic dialdehyde, ⁇ -isopropylsuccinic dialdehyde, ⁇ , ⁇ -diethylsuccinic dialdehyde, butylmaleic dialdehyde, and bisulfite adducts of these aldehydes.
  • dialdehyde hardeners are generally used in amounts of from 0.001 to 0.3 moles per liter, preferably of from 0.01 to 0.1 moles per liter of developer.
  • Antioxidants are generally sulfites.
  • sulfites we mean here those compounds known in the art as capable of generating sulfite ions (SO 3 -- ) in aqueous solutions and include sulfites, bisulfites, metabisulfites (1 mole of metabisulfite forming 2 moles of bisulfite in aqueous solution) and aldehyde bisulfite adducts.
  • sulfites, bisulfites, metabisulfites include sodium sulfite, sodium bisulfite, sodium metabisulfite, potassium sulfite, potassium bisulfite, potassium metabisulfite and ammonium metabisulfite.
  • the amount of the total sulfite ions is preferably not less than 0.05 moles, more preferably 0.1 to 1.25 moles, and most preferably 0.3 to 0.9 moles, per liter of developer.
  • the molar ratio of the sulfite ions with respect to the hydroquinone is at least 1.5:1, preferably exceeds 2:1 and, more preferably, is between 2.5:1 to 4:1.
  • Antifoggants which are known in the art to control the fog appearence in processed photographic materials, useful in the developer of the present invention include benzimidazole-, benzotriazole-, mercaptoazole-, indazole-and mercaptothiadiazole-type antifoggants.
  • Preferred antifoggants include 5-nitroindazole, benzimidazole nitrate, 5-methylbenzotriazole and 1-phenyl-5-mercaptotetrazole. Said compounds are used, alone or in combination, in amounts of from about 1x10 -6 to about 5x10 -1 moles per liter, preferably of from about 5x10 -4 to about 1x10 -1 moles per liter of the developer.
  • the developer comprises a combination of benzotriazole-, indazole- and mercaptoazole-type antifoggants, more preferably a combination of 5-methylbenzotriazole, 5-nitroindazole and l-phenyl-5-mercaptotetrazole.
  • said combination comprises from 7x10 -5 to 0.04 moles per liter of said benzotriazole-type antifoggant, from 6x10 -6 to 0.03 moles per liter of said indazole-type antifoggant and from 6x10 -6 to 0.02 moles per liter of said mercaptoazole type antifoggant. Examples of mercaptoazoles are described in US Pat. No.
  • the present invention relates to an alkaline aqueous black-and-white photographic developer, for processing a silver halide photographic material, particularly a silver halide radiographic material, comprising (1) at least one hydroquinone, (2) at least one 3-pyrazolidone developing agent, (3) at least one dialdehyde hardener, (4) at least one antifoggant, (5) a sequestering agent, (6) a sulfite antioxidant, and (7) a buffering agent, characterized in that said sequestering agent is a cyclicaminomethane diphosphonic acid compound, the molar ratio of the buffering agent to the sulfite antioxidant is at least 0.5:1, the molar ratio of the sulfite antioxidant to hydroquinone is at least 1.5:1 and the antifoggant comprises a combination of a benzotriazole-type antifoggant, an indazole-type antifoggant and a mercaptotetrazole
  • the developer in accordance with the present invention includes a buffer (e.g., carbonic acid salts, phosphoric acid salts, polyphosphates, metaborates, boric acid and boric acid salts).
  • a buffer e.g., carbonic acid salts, phosphoric acid salts, polyphosphates, metaborates, boric acid and boric acid salts.
  • the amount of the buffer with respect to the sulfite exceeds a molar ratio of 0.5:1 and, more preferably, is between 1:1 to 2:1.
  • inorganic alkaline agents to obtain the preferred pH which is usually higher than 10.
  • Said inorganic alkaline agents include KOH, NaOH, LiOH, sodium and potassium carbonate, etc.
  • adjuvants well known to the skilled in the art of developer formulation may be added to the developer of the present invention.
  • these include restrainers, such as the soluble halides (e.g., KBr), solvents (e.g., polyethylene glycols and esters thereof), development accelerators (e.g., polyethylene glycols and pyrimidinium compounds), preservatives, surface active agents, and the like.
  • the developer of the invention is prepared by dissolving the ingredients in water and adjusting the pH to the desired value.
  • the developer may also be prepared in a concentrated form and then diluted to a working strength just prior to use.
  • the developer may be prepared in two or more concentrated parts to be combined and diluted with water to the desired strength and placed in the developer tank of the automatic processing machine.
  • the developer of the present invention is particularly useful when processing is carried out in automatic processing machines.
  • Automatic processing machines may be of the type described in US Pat. No. 3,545,971, such as an "X-OMAT Processor” made by Eastman Kodak Company, of the series of "TRIMATIC” Processors made by 3M Company and of the type of "Model RK” made by Fuji Photo Film Company.
  • the developing temperature and the developing time are in relation to each other and are dependant on the total processing time. In general, they are about 20°C to 50°C, and 10 seconds to 1.5 minutes, respectively.
  • the silver halide material is fixed, preferably in an acid fixer, and washed and dried in the usual manner.
  • these steps are determined by the machine.
  • the silver halide photographic materials which can be used in the present invention comprise a support and at least one silver halide emulsion layer coated on the support.
  • the silver halide emulsion layer may be coated on one side of the support or on both sides thereof.
  • the silver halide photographic element can comprise other non light-sensitive layers, such as backing layers, antihalation layers, interlayers, filter layers, protective layers.
  • the silver halide emulsion comprise silver halide grains (such as silver chloride, silver bromide, silver chlorobromide, silver bromoiodide, silver chlorobromoiodide) dispersed in an hydrophilic colloid (such as gelatin, modified gelatins, albumin, casein, sodium alginate, carboxymethyl cellulose, polyvinyl alcohol, polyvinyl pyrrolidone and mixtures thereof).
  • the emulsion can contain cubic, octahedral, spherical and/or tabular silver halide grains.
  • the emulsion can be chemical and optical sensitized and added during its manufacture or before its coating various additives, such as stabilizers, antifoggants, hardeners, coating aids, etc.
  • the silver halide emulsion is coated on a support such as a cellulose acetate film, or a polyethylene terephthalate film using coating methods well known in the art, and dried.
  • the silver halide photographic materials to be used in the present invention are preferably black-and-white radiographic materials of high gradation (contrast) and particularly preferably materials which provide a gradation of 1.5 to 4.0.
  • a double layer coated radiographic film 3M type XD-A and a single layer coated radiographic film 3M type MS-3 were processed using developers 5 and 6, fresh and oxidized, for 20 seconds at 35°C, followed by fixing in 3M XAF/3 Fixer for 24 seconds at 30°C, washing in tap water for 22 seconds at 35°C and drying for 22 seconds at 35°C.
  • a green sensitive double layer coated radiographic film 3M type XD-A and a blue sensitive double layer coated radiographic film 3M type R-2 were processed using the developers above for 20 seconds at 39°C, followed by fixing in 3M XAF/3 Fixer for 24 seconds at 30°C, washing in tap water for 22 seconds at 35°C and drying for 22 seconds at 35°C.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Photographic Processing Devices Using Wet Methods (AREA)

Claims (8)

  1. Wäßrig alkalischer photographischer Schwarzweißentwickler, umfassend
    (1) ein Hydrochinon,
    (2) ein 3-Pyrazolidon-Entwicklungsmittel,
    (3) ein Dialdehyd-Härtungsmittel,
    (4) mindestens ein Antischleiermittel,
    (5) ein Maskierungsmittel,
    (6) ein Sulfit als Antioxidans, und
    (7) einen Puffer,
    wobei das Maskierungsmittel eine cyclische Aminomethandiphosphonsäureverbindung ist, das Molverhältnis des Puffers zu dem Sulfit als Antioxidans mindestens 0,5 : 1 beträgt, und das Molverhältnis des Sulfits als Antioxidans zu Hydrochinon mindestens 1,5 : 1 beträgt.
  2. Wäßrig alkalischer Entwickler nach Anspruch 1, wobei das Molverhältnis des Puffers zu dem Sulfit als Antioxidans in dem Bereich von 1 : 1 bis 2 : 1 liegt.
  3. Wäßrig alkalischer Entwickler nach Anspruch 1, wobei die cyclische Aminomethandiphosphonsäureverbindung der nachstehenden Formel entspricht
    Figure imgb0007
     wobei R1, R2 und R3, die gleich oder verschieden sein können, jeweils ein Wasserstoffatom oder einen PO3M'M"-Rest bedeuten, wobei M' und M" ein Wasserstoffatom, ein Alkalimetall oder eine quatemäre Ammoniumgruppe bedeuten, und Q die Atome oder chemischen Bindungen darstellt, die notwendig sind, einen 3- bis 6-gliedrigen Ring zu vervollständigen, mit der Maßgabe, daß mindestens zwei der Substituenten R1, R2 und R3 einen PO3M'M"-Rest bedeuten.
  4. Wäßrig alkalischer Entwickler nach Anspruch 1, wobei das Maskierungsmittel der Formel
    Figure imgb0008
     entspricht.
  5. Wäßrig alkalischer Entwickler nach Anspruch 1, wobei das Maskierungsmittel in einer Menge von 5x10-4 bis 5x10-1 Mol pro Liter des Entwicklers verwendet wird.
  6. Wäßrig alkalischer Entwickler nach Anspruch 5, wobei das Hydrochinon in dem Entwickler in einer Menge von 0,075 bis 0,75 Mol pro Liter vorliegt, das 3-Pyrazolidon-Entwicklungsmittel in einer Menge von 3x10-4 bis 0,15 Mol pro Liter vorliegt, das Dialdehyd-Härtungsmittel in einer Menge von 1x10-3 bis 0,3 Mol pro Liter vorliegt, die Antischleiermittel in einer Menge von 1x10-6 bis 0,1 Mol pro Liter vorliegen, das Molverhältnis des Sulfits als Antioxidans zu Hydrochinon mindestens 1,5 : 1 beträgt, und das Molverhältnis des Puffers zu dem Sulfit als Antioxidans mindestens 0,5 : 1 beträgt.
  7. Wäßrig alkalischer Entwickler gemäß den Ansprüchen 1 bis 6, wobei die Antischleiermittel eine Kombination eines Antischleiermittels des Benzotriazoltyps, eines Antischleiermittels des Indazoltyps und eines Antischleiermittels des Mercaptotetrazoltyps umfassen.
  8. Wäßrig alkalischer Entwickler nach Anspruch 7, wobei die Kombination der Antischleiermittel von 7x10-5 bis 0,04 Mol pro Liter des Antischleiermittels des Benzotriazoltyps, von 6x10-6 bis 0,03 Mol pro Liter des Antischleiermittels des Indazoltyps und von 6x10-6 bis 0,02 Mol pro Liter des Antischleiermittels des Mercaptotetrazoltyps umfaßt.
EP90124427A 1990-03-12 1990-12-17 Alkalischer photographischer Schwarzweissentwickler Expired - Lifetime EP0446457B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT1964590 1990-03-12
IT19645A IT1240596B (it) 1990-03-12 1990-03-12 Sviluppatore fotografico alcalino in bianco e nero

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EP0446457A2 EP0446457A2 (de) 1991-09-18
EP0446457A3 EP0446457A3 (en) 1992-02-26
EP0446457B1 true EP0446457B1 (de) 1996-10-30

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389502A (en) * 1994-02-08 1995-02-14 Eastman Kodak Company Hardening developer for silver halide photography and development method
JP3449128B2 (ja) * 1996-08-30 2003-09-22 信越半導体株式会社 単結晶成長方法
DE19644226A1 (de) * 1996-10-24 1998-04-30 Agfa Gevaert Ag Fixierbad
DE10257939A1 (de) * 2002-12-12 2004-06-24 Herbert Hafner Fotografisches Entwicklerbad

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0307867A2 (de) * 1987-09-14 1989-03-22 Konica Corporation Lichtempfindliches photographisches Silberhalogenidmaterial mit einer ausgezeichneten Schärfe und anwendbar für Ultraschnellbehandlung

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2246610C3 (de) * 1972-09-22 1980-01-03 Agfa-Gevaert Ag, 5090 Leverkusen Photographischer Farbentwickler
US4264716A (en) * 1979-09-10 1981-04-28 Eastman Kodak Company Photographic color developer compositions
IT1175017B (it) * 1983-09-20 1987-07-01 Minnesota Mining & Mfg Composizioni di sviluppo per materiali fotografici agli alogenuri d'argento
JPH0690455B2 (ja) * 1986-07-02 1994-11-14 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法
IT1215423B (it) * 1987-04-13 1990-02-08 Minnesota Mining & Mfg Composizioni di sviluppo per materiali fotografici agli alogenuri d'argento.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0307867A2 (de) * 1987-09-14 1989-03-22 Konica Corporation Lichtempfindliches photographisches Silberhalogenidmaterial mit einer ausgezeichneten Schärfe und anwendbar für Ultraschnellbehandlung

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IT9019645A1 (it) 1991-09-12
EP0446457A3 (en) 1992-02-26
IT1240596B (it) 1993-12-17
JPH04219753A (ja) 1992-08-10
EP0446457A2 (de) 1991-09-18
JP2989289B2 (ja) 1999-12-13
DE69029032D1 (de) 1996-12-05
DE69029032T2 (de) 1997-03-06
IT9019645A0 (it) 1990-03-12

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