EP0228940A1 - Verfahren zum Extrahieren von Uran und/oder Plutonium IV aus einer wässrigen Lösung mittels N,N-Dialkylamiden - Google Patents

Verfahren zum Extrahieren von Uran und/oder Plutonium IV aus einer wässrigen Lösung mittels N,N-Dialkylamiden Download PDF

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Publication number
EP0228940A1
EP0228940A1 EP86402671A EP86402671A EP0228940A1 EP 0228940 A1 EP0228940 A1 EP 0228940A1 EP 86402671 A EP86402671 A EP 86402671A EP 86402671 A EP86402671 A EP 86402671A EP 0228940 A1 EP0228940 A1 EP 0228940A1
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plutonium
uranium
organic phase
mol
aqueous solution
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EP0228940B1 (de
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Nicole Descouls
Jean-Claude Morisseau
Claude Musikas
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Commissariat a lEnergie Atomique et aux Energies Alternatives CEA
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    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22B—PRODUCTION AND REFINING OF METALS; PRETREATMENT OF RAW MATERIALS
    • C22B60/00—Obtaining metals of atomic number 87 or higher, i.e. radioactive metals
    • C22B60/02—Obtaining thorium, uranium, or other actinides
    • C22B60/0204—Obtaining thorium, uranium, or other actinides obtaining uranium
    • C22B60/0217—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes
    • C22B60/0252—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries
    • C22B60/026—Obtaining thorium, uranium, or other actinides obtaining uranium by wet processes treatment or purification of solutions or of liquors or of slurries liquid-liquid extraction with or without dissolution in organic solvents

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  • the present invention relates to a process for extracting U (VI) ions and / or Pu (IV) ions present in an acidic aqueous solution using N, N-dialkylamides.
  • One of the usual practices for reprocessing spent nuclear fuel is to first dissolve the combustible material in a nitric solution, then treat this solution by extraction with an organic solvent to separate the uranium and plutonium from the fission products and then separate the uranium from the plutonium.
  • an organic solvent generally consisting of tributyl phosphate is generally used, and the uranium is then separated from the plutonium extracted in the organic solvent by contacting the latter with an aqueous nitric solution. containing reducing agents to reduce plutonium (IV) to plutonium (III) and pass it through the aqueous solution.
  • reducing agents usually used such as valence iron (II), valence uranium (IV) or hydroxylamine (NH2OH) are not stable in the presence of nitric acid because they tend to be oxidized by him.
  • an anti-nitrite agent such as hydrazine (NH2-NH2) is added to the nitric solution.
  • nitric solution also contains technetium, which is generally the case, because tributyl phosphate also extracts a significant part of the technetium present in the solutions for dissolving irradiated nuclear fuels.
  • technetium catalyzes the oxidation of hydrazine by nitric acid, thus preventing hydrazine from playing its role of stabilizing the reducing agents of Pu (IV). Because of this, an oxidation of the reducing agents also occurs, thus preventing the reduction of the plutonium and therefore its re-extraction in the aqueous solution.
  • the present invention specifically relates to the use of new N, N-dialkylamides for extracting uranium and / or plutonium present in nitric solutions from the reprocessing of irradiated nuclear fuels, which overcomes the aforementioned drawback.
  • the process according to the invention for extracting uranium VI and / or plutonium (IV) from an organic phase present in an acidic aqueous solution by bringing this solution into contact with this organic phase is characterized in that the organic phase comprises an inert diluent and at least one extractant consisting of an N, N-dialkylamide of formula: in which R1 is a linear or branched alkyl radical of 2 to 12 carbon atoms, R2 and R4 which may be the same or different are radi linear or branched alkyl cals of 2 to 4 carbon atoms, R3 and R5 which may be identical or different are linear or branched alkyl radicals of 1 to 6 carbon atoms, and a and b which may be identical or different are numbers integers ranging from 1 to 6.
  • radicals R2 and R4 both represent the ethyl radical.
  • N, N-dialkylamides it is possible to obtain a solubility of the uranium complexes of at least 100 g of uranium per liter of organic phase, which is sufficient on an industrial scale.
  • N, N-dialkylamides of the invention aliphatic carbides such as linear or branched saturated hydrocarbons can be used as diluent and thereby obtain the following advantages: the organic phase has a lower density, which allows the settling of the phases under better conditions, and - saturated hydrocarbons have better chemical stability in nitric medium, points higher flashes, and they are less toxic than aromatic carbides which were previously used as diluents.
  • N N-dialkylamides which can be used in the invention, there may be mentioned: - N, N-di (2-ethylhexyl) dimethyl-2,2 butyramide (DOTA) of formula: - N, N-di (2-ethylhexyl) hexanamide (DOHA), of formula: - N, N-di (2-ethylhexyl) dodecanamide (DODA) of formula: - N, N-di (2-ethylhexyl) octanamide (DOOA) of formula:
  • DOTA N-di (2-ethylhexyl) dimethyl-2,2 butyramide
  • DOHA N, N-di (2-ethylhexyl) hexanamide
  • DODA N-di (2-ethylhexyl) dodecanamide
  • DOOA N-di (2-ethylhexyl) octanamide
  • N, N-dialkylamides used in the invention can be prepared according to conventional methods by reaction of the acid chloride of formula: R1COCl with the secondary amine of formula: in which R1, R2, R3, R4, R5, a and b have the meaning given above.
  • the starting secondary amines can also be prepared by conventional methods, for example by reaction of the corresponding alcohols of formula: with ammonia. In this case, a mixture of primary, secondary and tertiary amines is formed and the desired secondary amine can be separated by fractional distillation.
  • N, N-dialkylamides of the invention corresponds to the following reaction scheme:
  • the product obtained is then purified by distillation under reduced pressure and generally 99% pure amides are obtained.
  • dialkylamides of the invention for the treatment of aqueous solutions containing simultaneously uranium (VI) and plutonium (IV) is very advantageous because it is possible by adjusting the acidity of the starting aqueous solution, which is generally a nitric solution, either extract simultaneously the uranium (VI) and the plutonium (IV), or selectively extract the uranium (VI) leaving the plutonium (IV) in aqueous solution without it being necessary to use reducing agents.
  • the acidity of the aqueous solution is adjusted to a value of at least 2N to simultaneously extract uranium (VI) and plutonium (IV) in the organic phase.
  • the acidity of the latter is adjusted to a value of 3 to 10 N in order to obtain the best plutonium and uranium extraction rates in the organic phase.
  • the acidity of the aqueous solution is adjusted to a value of 0.5 to 1.2 N to selectively extract the uranium (VI) in the organic phase.
  • an N, N-dialkylamide is used in which the radical R1 is a branched alkyl radical.
  • an N, N-dialkylamide is preferably used in which the radical R1 is a linear alkyl radical.
  • the concentration of N, N-dialkylamide in the organic phase is preferably from 0.2 to 2 mol.l ⁇ 1.
  • the extraction rate generally increases with the concentration of N, N-dialkylamide in the organic phase.
  • the N, N-dialkylamide content of the organic phase is generally limited to a value of 1.5 mol.l ⁇ 1.
  • the diluents which can be used in the invention are inert organic diluents preferably having a low dielectric constant.
  • diluents examples include benzene, xylene, mesitylene, tert-butylbenzene, decanol and aliphatic hydrocarbons, in particular linear or branched saturated hydrocarbons.
  • an aliphatic hydrocarbon is used as diluent, in particular a linear or branched saturated hydrocarbon such as dodecane, for example the product sold under the brand Hyfran because, as we have seen previously, the use of such diluents provides many advantages.
  • the method of the invention can be implemented in any conventional extraction apparatus such as batteries of mixer-settlers, pulsed columns, centrifugal extractors, etc.
  • aqueous phase / organic phase volume ratios which can vary from 10 to 0.1.
  • the uranium (VI) and plutonium (IV) extracted in the organic phase can then be recovered with very good yield at room temperature by contacting the organic solvent with dilute nitric acid for uranium (VI ) (0 to 0.2N) and more concentrated nitric acid for Pu (IV) (0.5 to 1.5N).
  • N, N-dialkylamides are not very troublesome whereas, in the case of tributyl phosphate, it is not the same since they generally precipitate.
  • N, N-dialkylamides can be destroyed by incineration, giving only gaseous waste, while tributyl phosphate gives phosphoric acid as the main waste.
  • N, N-dialkylamides allow the uranium (VI) to be separated directly from the plutonium (IV), whereas in the case of tributyl phosphate, it is necessary to use reducing agents such as hydrazine and hydroxylamine.
  • N, N-dialkylamides makes it easy to separate zirconium from uranium (VI) and plutonium (IV), which was not the case with tributyl phosphate.
  • N, N-dialkylamides of the invention do not pose any particular problem and they can thus be manufactured at attractive prices.
  • FIGS. 1 to 6 are diagrams illustrating the variations in the distribution coefficient of Pu (IV) or U (VI) as a function of the concentrations of nitric acid in the starting aqueous solution or of the concentrations of N, N- dialkylamide of the organic phase,
  • FIGS. 7 to 9 are diagrams representing the variations in the distribution coefficients of different fission products and of nitric acid as a function of the concentration of nitric acid in the aqueous solution
  • FIG. 10 is a diagram representing the variations in the distribution coefficients of U (VI), Pu (IV) and Zr (IV) as a function of the concentration of nitric acid in the aqueous solution, and
  • FIGS 11 to 13 are diagrams illustrating the variations of the distribution coefficients of U (VI) and Pu (IV) as a function of the nitric acid concentration of the aqueous solution, for different N, N-dialkylamides.
  • This example illustrates the extraction of U (VI) from an aqueous nitric solution containing 10 ⁇ 4 mol.l ⁇ 1 of U (VI).
  • an organic phase consisting of the product sold under the brand Hyfran 120, which is branched dodecane, containing 0.5 mol.l ⁇ 1 of N, N-di (2-ethylhexyl) 2-dimethyl, 2 butyramide (DOTA).
  • the organic phase and the aqueous phase containing the U (VI) are brought into contact with stirring with an organic phase / aqueous phase volume ratio equal to 1.
  • curve 1 illustrates the variations in the distribution coefficient of uranium D U (VI) as a function of the concentration of nitric acid (in mol.l ⁇ 1).
  • curve 2 in FIG. 1 which illustrates the variations in the distribution coefficient of uranium D U (VI) as a function of the concentration of nitric acid.
  • an aqueous nitric solution containing 10 ⁇ 4 mol.l ⁇ 1 of U (VI) is used and 0.98 mol.l ⁇ 1 of HNO3, and an organic phase consisting of Hyfran 120 containing variable amounts of the N, N-dialkylamide used in Example 1 (DOTA).
  • Example 4 the same procedure is followed as in Example 4, but the aqueous nitric solution has a nitric acid concentration of 4.9 mol.l ⁇ 1.
  • This example concerns the extraction of Pu (IV) present at a concentration of 5 ⁇ 10 ⁇ 5 mol.l ⁇ 1 in an aqueous nitric solution.
  • Example 7 the same procedure is followed as in Example 7, but using the N, N-dialkylamide of Example 2 (DOHA).
  • Example 7 The same procedure is followed as in Example 7 but using an aqueous nitric solution having a nitric acid concentration of 0.98 mol.l ⁇ 1 and varying the concentration of N, N-dialkylamide (DOTA) of the organic phase.
  • aqueous nitric solution having a nitric acid concentration of 0.98 mol.l ⁇ 1 and varying the concentration of N, N-dialkylamide (DOTA) of the organic phase.
  • DOTA N, N-dialkylamide
  • Example 9 the same procedure is followed as in Example 9, but the N, N-dialkylamide of Example 2 (DOHA) is used.
  • DOHA N, N-dialkylamide of Example 2
  • Example 9 The same procedure is followed as in Example 9, but using an aqueous nitric solution having a nitric acid concentration of 4.9 mol.l ⁇ 1.
  • Example 2 the same procedure is followed as in Example 1, but using an aqueous nitric solution containing 5 ⁇ 10 ⁇ 5 mol.l ⁇ 1 of Pu (IV) and 10 ⁇ 4 mol.l ⁇ as the aqueous solution. 1 of U (VI), and an organic phase consisting of tale Hyfran nant. 1 mol.l ⁇ 1 of N, N-dialkylamide of Example 2 (DOHA).
  • curve 13a represents the distribution coefficient D Pu (IV) as a function of the concentration of nitric acid in the aqueous solution
  • curve 13b represents the distribution coefficient D U (VI) in depending on the nitric acid concentration of the aqueous solution.
  • a uranium-plutonium separation can be obtained for nitric acid concentrations of less than 2 mol.l ⁇ 1, in particular for concentrations of 0.5 to 1.2 mol.l ⁇ 1 .
  • Example 13 the same procedure is followed as in Example 13, but using an organic phase consisting of Hyfran containing 0.5 mol.l ⁇ 1 of the N, N-dialkylamide of Example 1 (DOTA). .
  • This example illustrates the extraction of different fission products by the N, N-dialkylamides of the invention.
  • Example 2 The same procedure is followed as in Example 1, but using an organic phase consisting of Hyfran containing 1 mol.l ⁇ 1 of the N, N-dialkylamide of Example 2 (DOHA).
  • the distribution coefficient is less than 10 ⁇ 3.
  • Example 15 the same procedure is followed as in Example 15, but using the dialkylamide of Example 1 (DOTA) instead of DOHA.
  • DOHA dialkylamide of Example 1
  • aqueous nitric solutions having varying concentrations of nitric acid are brought into contact with an organic phase consisting of Hyfran containing either 0.5 mol.l ⁇ 1, or 1 mol.l ⁇ 1 of N, N -dialkylamide of Example 2 (DOHA).
  • the aqueous phase is brought into contact with the organic phase under the same conditions as those of Example 1 and, after settling of the phases, the concentration of nitric acid in the organic phase is determined (in mol.l ⁇ 1 ).
  • curves 17a and 17b illustrate the variations in the concentrations of nitric acid in the organic phase as a function of the concentration in nitric acid in the aqueous phase.
  • Curve 17a relates to the organic phase containing 0.5 mol.l ⁇ 1 of DOHA and curve 17b relates to the organic phase containing 1 mol.l ⁇ 1 of DOHA.
  • Example 2 the same procedure is followed as in Example 1, using aqueous nitric solutions containing 10 ⁇ 4 mol.l ⁇ 1 of U (VI), 5 ⁇ 10 ⁇ 5 mol.l ⁇ 1 of Pu (IV ) and 5 ⁇ 10 ⁇ 3 mol.l ⁇ 1 of Zr (IV) and having different concentrations of nitric acid, and an organic phase consisting either of dodecane containing 1.09 mol.l ⁇ 1 of tributyl phosphate, or with Hyfran containing 1 mol.l ⁇ 1 of DOHA.
  • curves 18a, 18b, 18c respectively illustrate the variations in the distribution coefficients of U (VI), Pu (IV) and Zr (IV) as a function of the concentration in nitric acid in the aqueous solution in the case of the organic phase consisting of dodecane containing 1.09 mol.l ⁇ 1 of tributyl phosphate
  • curves 19a, 19b and 19c respectively illustrate the distribution coefficients of U ( VI), Pu (IV) and Zr (IV) as a function of the nitric acid concentration of the aqueous solution in the case of the organic phase containing 1 mol.l ⁇ 1 of DOHA.
  • each organic phase having the composition given in the attached table is placed with an aqueous nitric phase containing uranium, bringing the mixture into contact with stirring for 4 min.
  • the two phases are then allowed to settle and their concentrations of uranium and nitric acid or of H+ ions are determined.
  • the results obtained are given in the attached table on which, moreover, it was indicated how the uranium complex formed and extracted in the organic phase behaved, and what was the percentage of uranium saturation of the organic phase.
  • N, N-dialkylamides of the invention make it possible to obtain a satisfactory extraction of uranium (at least 100 g per liter) without observing crystallization or precipitation of the extracted complex, or a phenomenon of demixing in the organic phase.
  • Example 2 the same procedure is followed as in Example 1, but using as an aqueous solution an aqueous nitric solution containing 5 ⁇ 10 ⁇ 5 mol.l ⁇ 1 of Pu (IV) and 10 ⁇ 4 mol.l ⁇ 1 of U (VI), and an organic phase consisting of Hyfran containing 1.07 mol.l ⁇ 1 of N, N-dialkylamide (iDOPA) of formula:
  • FIG. 11 represents the variations in the distribution coefficients of plutonium (IV) and uranium (VI) as a function of the concentration of nitric acid in the aqueous solution, in logarithmic coordinates.
  • FIG. 12 represents in logarithmic coordinates the variations in the distribution coefficients of uranium (VI) and plutonium (IV) as a function of the concentration of nitric acid in the aqueous solution.
  • Example 30 The same procedure is followed as in Example 30, but an organic phase is used which consists of Hyfran containing 1.03 mol.l ⁇ 1 of N, N-dialkylamide (iDOBA) of formula:
  • FIG. 13 represents the variations in the distribution coefficients of U (VI) and Pu (IV) as a function of the concentration of nitric acid in the aqueous solution.
  • dialkylamides of Examples 30 to 32 are interesting for the U / Pu separation because the solubility of the nitrate salts of uranyl in these dialkylamides is high, around 150 gl ⁇ 1 of uranium.

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EP86402671A 1985-12-05 1986-12-02 Verfahren zum Extrahieren von Uran und/oder Plutonium IV aus einer wässrigen Lösung mittels N,N-Dialkylamiden Expired - Lifetime EP0228940B1 (de)

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FR8518015 1985-12-05
FR8518015A FR2591213B1 (fr) 1985-12-05 1985-12-05 Procede d'extraction de l'uranium vi et/ou du plutonium iv presents dans une solution aqueuse au moyen de n,n-dialkylamides

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
FR2642562A1 (fr) * 1989-02-01 1990-08-03 Commissariat Energie Atomique Procede d'extraction de l'uranium vi et/ou du plutonium iv presents dans une solution aqueuse acide au moyen d'un melange de n,n-dialkylamides, utilisable pour le retraitement de combustibles nucleaires irradies
FR2642561A1 (fr) * 1989-02-01 1990-08-03 Commissariat Energie Atomique Procede pour separer l'uranium vi du thorium iv presents dans une solution aqueuse au moyen d'un n, n-dialkylamide, utilisable notamment pour separer l'uranium produit par irradiation du thorium
EP0505277A1 (de) * 1991-03-21 1992-09-23 Commissariat A L'energie Atomique Verfahren zur Abtrennung von Eisen und/oder Zirkonium aus Aktiniden und/oder Lanthaniden enthaltenden wässrigen Säurelösungen mittels eines Propandiamids
FR2840446A1 (fr) * 2002-06-04 2003-12-05 Japan Nuclear Cycle Dev Inst Procede de retraitement d'un combustible nucleaire epuise
FR3062128A1 (fr) * 2017-01-26 2018-07-27 Commissariat A L'energie Atomique Et Aux Energies Alternatives N,n-dialkylamides dissymetriques, utiles notamment pour separer l'uranium(vi) du plutonium(iv), leur synthese et leurs utilisations

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FR2954354B1 (fr) * 2009-12-22 2012-01-13 Commissariat Energie Atomique Procede de purification de l'uranium d'un concentre d'uranium naturel
US8741237B1 (en) * 2010-04-12 2014-06-03 U.S. Department Of Energy Solvent extraction system for plutonium colloids and other oxide nano-particles
FR2960690B1 (fr) * 2010-05-27 2012-06-29 Commissariat Energie Atomique Procede de traitement de combustibles nucleaires uses ne necessitant pas d'operation de desextraction reductrice du plutonium
FR3039696B1 (fr) * 2015-07-29 2017-07-28 Commissariat Energie Atomique Procede de traitement en un cycle, exempt d'operation de desextraction reductrice du plutonium, d'une solution aqueuse nitrique de dissolution d'un combustible nucleaire use
FR3039547B1 (fr) * 2015-07-29 2017-08-25 Areva Nc Nouveaux n,n-dialkylamides dissymetriques, leur synthese et leurs utilisations
JP6961427B2 (ja) 2017-09-01 2021-11-05 株式会社エフ・シー・シー 動力伝達装置
JP6502443B2 (ja) 2017-09-01 2019-04-17 株式会社エフ・シー・シー 動力伝達装置

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FR2537326A1 (fr) * 1982-12-01 1984-06-08 Commissariat Energie Atomique Procede de recuperation des actinides et/ou des lanthanides presents a l'etat trivalent dans une solution aqueuse acide
US4574072A (en) * 1983-07-26 1986-03-04 The United States Of America As Represented By The United States Department Of Energy Method for extracting lanthanides and actinides from acid solutions by modification of purex solvent

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2642562A1 (fr) * 1989-02-01 1990-08-03 Commissariat Energie Atomique Procede d'extraction de l'uranium vi et/ou du plutonium iv presents dans une solution aqueuse acide au moyen d'un melange de n,n-dialkylamides, utilisable pour le retraitement de combustibles nucleaires irradies
FR2642561A1 (fr) * 1989-02-01 1990-08-03 Commissariat Energie Atomique Procede pour separer l'uranium vi du thorium iv presents dans une solution aqueuse au moyen d'un n, n-dialkylamide, utilisable notamment pour separer l'uranium produit par irradiation du thorium
EP0381579A1 (de) * 1989-02-01 1990-08-08 Commissariat A L'energie Atomique Verfahren zur Extraktion vom in einer wässerigen sauren Lösung befindlichen Uran-(VI) und/oder Plutonium-(IV) mittels einer Mischung von N,N-Dialkylamiden, verwendbar bei der Wiederaufarbeitung von bestrahlten Kernbrennstoffen
US5132092A (en) * 1989-02-01 1992-07-21 Commissariat A L'energie Atomique Process for the extraction of uranium (vi) and/or plutonium (iv) present in an acid aqueous solution by means of a mixture of n,n-dialkyl amides usable for the reprocessing of irradiated nuclear fuels
EP0505277A1 (de) * 1991-03-21 1992-09-23 Commissariat A L'energie Atomique Verfahren zur Abtrennung von Eisen und/oder Zirkonium aus Aktiniden und/oder Lanthaniden enthaltenden wässrigen Säurelösungen mittels eines Propandiamids
FR2674256A1 (fr) * 1991-03-21 1992-09-25 Commissariat Energie Atomique Procede pour separer le fer et/ou le zirconium des actinides et/ou des lanthanides presents dans une solution aqueuse acide au moyen d'un propanediamide.
US5223232A (en) * 1991-03-21 1993-06-29 Commissariat A L'energie Atomique Process for separating iron and/or zirconium from the actinides and/or lanthanides present in an aqueous acid solution by means of a propane diamide
FR2840446A1 (fr) * 2002-06-04 2003-12-05 Japan Nuclear Cycle Dev Inst Procede de retraitement d'un combustible nucleaire epuise
FR3062128A1 (fr) * 2017-01-26 2018-07-27 Commissariat A L'energie Atomique Et Aux Energies Alternatives N,n-dialkylamides dissymetriques, utiles notamment pour separer l'uranium(vi) du plutonium(iv), leur synthese et leurs utilisations
WO2018138441A1 (fr) * 2017-01-26 2018-08-02 Commissariat A L'energie Atomique Et Aux Energies Alternatives N,n-dialkylamides dissymétriques, utiles notamment pour séparer l'uranium(vi) du plutonium(iv), leur synthèse et leurs utilisations
GB2572921A (en) * 2017-01-26 2019-10-16 Commissariat Energie Atomique Dissymmetric N,N-Dialkylamides used particularly for separating uranium(VI) from plutonium(IV), Synthesis thereof and uses of same
RU2762634C2 (ru) * 2017-01-26 2021-12-21 Коммиссариат А Л' Энержи Атомик Э Оз Энержи Альтернатив Несимметричные n,n-диалкиламиды, в частности используемые для отделения урана(vi) от плутония(iv), их синтез и применение
GB2572921B (en) * 2017-01-26 2022-01-26 Commissariat Energie Atomique Dissymmetric N,N-Dialkylamides used particularly for separating uranium(VI) from plutonium(IV), Synthesis thereof and uses of same
US11578031B2 (en) 2017-01-26 2023-02-14 Commissariat À L'Énergie Atomique Et Aux Ênergies Alternatives Dissymmetric N,N-dialkylamides used particularly for separating uranium(VI) from plutonium(IV), synthesis thereof and uses of same

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FR2591213B1 (fr) 1988-02-05
FR2591213A1 (fr) 1987-06-12
DE3673370D1 (de) 1990-09-13
US4772429A (en) 1988-09-20
JPS62143827A (ja) 1987-06-27
JPH06104573B2 (ja) 1994-12-21
EP0228940B1 (de) 1990-08-08

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