EP0390664B1 - Neue Thiophosphorverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schmiermittelzusatzstoffe - Google Patents

Neue Thiophosphorverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schmiermittelzusatzstoffe Download PDF

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Publication number
EP0390664B1
EP0390664B1 EP90400818A EP90400818A EP0390664B1 EP 0390664 B1 EP0390664 B1 EP 0390664B1 EP 90400818 A EP90400818 A EP 90400818A EP 90400818 A EP90400818 A EP 90400818A EP 0390664 B1 EP0390664 B1 EP 0390664B1
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EP
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Prior art keywords
composition according
phosphorus
mass
masse
additive
Prior art date
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EP90400818A
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English (en)
French (fr)
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EP0390664A3 (en
EP0390664A2 (de
Inventor
Guy Parc
Nicole Thevenin
Maurice Born
Jacques Lallement
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/241—Manufacturing joint-less pipes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/242—Hot working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/243—Cold working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/245—Soft metals, e.g. aluminum
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/251—Alcohol fueled engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • the present invention relates to new thiophosphorus compounds soluble in mineral oils obtained by reaction of at least one phosphorus sulfide with at least one so-called "overbased" detergent sulfonate.
  • an overbased detergent sulfonate can be defined as consisting of a surfactant consisting essentially of an alkaline or alkaline earth salt of a sulfonic acid containing oleophilic groups and which keeps acid salts in colloidal dispersion.
  • weak minerals such as CO2, H2S and alkaline or alkaline earth bases.
  • the reaction product between the phosphorus sulfide and the overbased detergent sulfonate can optionally be treated with at least one active hydrogen compound which can be water, an alcohol, a phenol, a carboxylic acid, a ester-acid, a mineral acid, a mineral base, an amine, an amide or a mercaptan.
  • active hydrogen compound can be water, an alcohol, a phenol, a carboxylic acid, a ester-acid, a mineral acid, a mineral base, an amine, an amide or a mercaptan.
  • the present invention also relates to the preparation of these new thiophosphorus compounds and their use as additives in mineral and synthetic lubricants.
  • these new additives have anti-wear and extreme-pressure properties which are particularly advantageous for application to engine oils, gear oils, hydraulic fluids, lubricating greases or oils for working with metals. .
  • Antiwear and extreme pressure additives are incorporated into lubricants when they are intended to lubricate organs subjected to significant mechanical stresses, such as distribution in heat engines, gears, bearings or stops. Significant mechanical stresses also appear during the machining of metals, whether cutting or forming.
  • transmission oils two types of additive are widely used: phospho-sulfur additives and additives based on potassium borate dispersion.
  • the main drawback of mineral oils containing phospho-sulfur additives is their thermal instability, which begins to manifest from 120-130 ° C. However, it is not uncommon for temperatures of 150 ° C to be reached in the transmissions of heavy goods vehicles or passenger cars used under severe conditions. Transmission oils based on potassium borate are significantly more thermally stable, but are sensitive to water, which is unacceptable for certain uses. More effective antiwear and extreme pressure additives, more thermally stable and having less interactions with other additives in the formulations are actively sought.
  • micellar thiophosphorus compounds of the present invention may be generally defined as being obtained by reaction of at least one overbased sulfonate (A) with a phosphorus sulfide (B), the reaction product possibly being brought into contact with at least one hydrogen compound active (C).
  • a and B, and optionally the subsequent treatment with C can advantageously be carried out in a solvent (D).
  • Compound A is an overbased sulfonate obtained from at least one alkali or alkaline earth metal salt of at least one acid compound chosen from sulfonic acids, natural or synthetic.
  • the overbasification of the alkali or alkaline earth metal salts of these acids is generally carried out in the presence of a promoter, by treating an excess of oxide or hydroxide of alkali or alkaline earth metal suspended in the reaction medium. , by a weak acid such as CO2, SO2, H2S, or H3BO3.
  • the most used cations for overbasification are sodium, magnesium, calcium and barium used in the form of their oxide or hydroxide.
  • the promoter is an alcohol, particularly methanol, an alkylphenol or an amino compound such as ammonia, an amine or an amino alcohol.
  • the most commonly used weak acid is CO2.
  • overbased additives The preparation of overbased additives is well known and is described for example in the patents: US 2,865,956, 3,150,088, 3,537,996, 3,830,739, 3,865,737, 4,148,740 and 4,505,830 and the French patent 2 101 813.
  • overbasing reaction which use in particular preformed carbonates from alkoxides and CO2 before being brought into contact with the alkaline or alkaline earth salt of the acid compound; they are described in particular in US patents 2,956,018, 3,932,289 and 4,104,180.
  • the sulfonic acids for the manufacture of overbased sulfonates which can be used according to the invention are known and described in numerous patents, for example in French patent 2 101 813, pages 5 and 6.
  • the hydrocarbon portion of the molecule advantageously has a molecular weight at less than 370 to ensure the miscibility of the corresponding sulfonates in mineral oils.
  • alkenyl hydrocarbons such as polyisobutenes (US patent 4,159,956)
  • alkylaryl hydrocarbons such as for example post-dodecylbenzenes obtained as tail product of the manufacture of dodecylbenzene.
  • overbased compounds A preferred according to the invention are the sodium or calcium sulfonates overbased with sodium carbonate or calcium carbonate.
  • the overbased sulfonates A that can be used according to the invention have an alkalinity expressed in terms of TBN (equivalent alkalinity expressed in milligrams of KOH per g of product) between 50 and 550 (or from 0.9 to 10 basic equivalents per kg) and preferably between 150 and 450 (i.e. 2.7 to 8 basic equivalents per kg).
  • TBN equivalent alkalinity expressed in milligrams of KOH per g of product
  • 150 and 450 i.e. 2.7 to 8 basic equivalents per kg.
  • Compound B is a phosphorus sulfide such as P4S7, P4S9, P4S10.
  • P4S10 is the preferred phosphorus sulfide according to the invention.
  • the molar quantity of compound C introduced relative to the molar quantity of phosphorus provided by the phosphorus sulphide can vary in a ratio of between 0.1 and 5, and preferably between 0.3 and 3.
  • the preferred compounds C according to the invention are ammonia, isopropanol, dialkylphosphites, boric acid, mercaptans, in particular derivatives of dimercaptothiadiazole.
  • the solvent D possibly used makes it possible to reduce the viscosity of the reaction medium and thus to improve the contact of the reactants.
  • solvents which can be used according to the invention, mention may be made of cyclohexane, toluene, xylenes and generally hydrocarbon fractions having a boiling range of between 60 and 150 ° C and preferably between 90 and 120 ° C.
  • the additives obtained according to the invention may have a certain reactivity with respect to copper alloys.
  • the use of sequestering additives of the dimercaptothiadiazole type at doses of between 0.25 and 0.75% by mass in the final formulations leads to entirely satisfactory behavior with respect to copper.
  • the required dose is lower when compound C is itself a mercaptothiadiazole derivative. It can range, for example, up to 0.5% by mass.
  • Another characteristic of the present invention is that, within the defined limits, the products obtained retain the colloidal state by giving solutions in the hydrocarbons perfectly clear and stable over time.
  • the process for manufacturing the compounds according to the invention comprises the following stages:
  • Step 1
  • the reaction of phosphorus sulfide on overbased sulfonate can be carried out at a pressure between atmospheric pressure and about 5 bar absolute (0.5 MPa), at a temperature between 60 and 130 ° C and preferably between 85 and 120 ° C.
  • the reaction between the phosphorus sulfide, solid reagent and the overbased additive is facilitated by good stirring of the reaction medium and by the possible use of a hydrocarbon solvent D.
  • the phosphorus sulfide can be gradually introduced into the reaction medium, but it can also be introduced entirely at the start of handling into the overbased compound optionally dissolved in a hydrocarbon solvent, provided that the temperature of the reaction medium is less than about 60 ° C.
  • the reaction is then started by gradually raising the temperature in the ranges indicated above.
  • Compound C with active hydrogen can be in gaseous, liquid or solid form and the means of introduction into the reaction medium will be appropriate to its physical state.
  • the reaction can be carried out at a pressure between atmospheric pressure and about 5 bar absolute (0.5 MPa), at a temperature between 60 and 130 ° C and preferably between 85 and 120 ° C.
  • filtration and elimination of solvents and any excess of reagent.
  • the filtration step is not always necessary, steps 1 and 2 leading in most cases to homogeneous liquid mixtures.
  • filtration can be carried out before the elimination of solvent D, for example on simple cellulose disks, or on layers of filtering agents of the diatomite type or of natural silica of volcanic origin. Filtration can also be carried out after removal of the solvents. In this case, it is advantageous to perform the filtration hot, for example from 90 to 120 ° C and under a pressure of 2 to 5 bars.
  • the distillation of the solvent can be carried out in the reactor itself.
  • the elimination of the last traces is facilitated by a nitrogen stripping. It can also be carried out in a thin film evaporator.
  • Example 6 The procedure is as in Example 6 until complete reaction of the P4S10. The temperature being maintained at 90 ° C., 49.5 g of didodecylphosphite dissolved in 50 ml of toluene are introduced over 1 hour. Then the temperature is brought to 115 ° C. and is maintained for 3 hours.
  • the anti-wear efficiency is evaluated on a 4-ball machine operating for 1 hour under loads of 40 and 60 daN at a speed of 1500 rpm, according to the NF E48-617 method.
  • the average footprint diameter observed on the 3 lower balls are as follows:
  • the extreme pressure properties in the lubricating oils of the products according to the invention were measured on an FZG gear machine according to the CEC method L-07-A-71 with the procedure A / 16.6 / 90, that is to say that is, using the type A gear, with a circumferential speed at the pitch diameter of 16.6 m / s and at a temperature of 90 ° C at the start of each load bearing.
  • the mineral oil used is the base 130 N described above. Method B of visual rating was used.
  • the extreme pressure efficiency is all the more pronounced the higher the load level reached.
  • the temperature of the oil was also recorded at the end of the bearing 12 which is in relation to the forces dissipated in the friction. A lower temperature translates to a lower coefficient of friction under the conditions of the test.
  • the results obtained are shown in the following table:
  • the objective of this test was to replace the antiwear additive and the detergent additive with an additive according to the invention.
  • a conventional dispersant additive of the succinimide type usually used to meet the requirements of cold dispersivity was used.
  • test bench is driven by an electric motor and operates according to the following cycle: 1 minute at 750 rpm 2 minutes at 1500 rpm
  • the springs, under maximum lift, are rated at 1200 N.
  • the duration of the test is 50 hours and the oil temperature is regulated at 50 ° C.
  • the rockers are weighed and rated according to a scale which defines four standard aspects.
  • This test uses a PEUGEOT PC7 bridge to which torque peaks of the order of 340 Nm are applied.
  • the crown is examined without dismantling all the series of 20 torque peaks.
  • the test is continued up to 80 peaks of torque, after which the bridge is dismantled and the surfaces of the pinion and the crown are examined.
  • the result is given as a percentage of the bearing surface deteriorated by seizing (scoring).
  • the additives are compared in an identical base oil (100 neutral solvent).
  • a comparative test was carried out with an extreme pressure additive marketed under the name of ANGLAMOL 99 (registered trademark), extreme pressure additive widely used in hypoid bridges.

Claims (15)

  1. Thiophosphor-Additiv-Zusammensetzung, dadurch gekennzeichnet, daß sie erhalten wird durch Umsetzung eines mit Natrium- oder Calciumcarbonat überbasisch gemachten Natrium- oder Calciumsulfonats, das 0,9 bis 10 Basenäquivalente pro kg aufweist, mit einem Phosphorsulfid, das in einem solchen Mengenanteil verwendet wird, daß das Molverhältnis von Phosphor zu Basenäquivalent des überbasisch gemachten Sulfonats 0,002 bis 0,15 beträgt.
  2. Zusammensetzung nach Anspruch 1, dadurch gekennzeichnet, daß das Phosphorsulfid ausgewählt wird aus der Gruppe P₄S₇, P₄S₉ und P₄S₁₀.
  3. Zusammensetzung nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß es sich bei dem Phosphorsulfid um P₄S₁₀ handelt.
  4. Zusammensetzung nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß die Reaktion bei einem Druck zwischen Atmosphärendruck und 0,5 MPa und bei einer Temperatur von 60 bis 130°C durchgeführt wird.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß sie im Milieu eines zwischen 60 und 150°C siedenden Kohlenwasserstoff-Lösungsmittels hergestellt worden ist.
  6. Thiophosphor-Additiv-Zusammensetzung, dadurch gekennzeichnet, daß sie nach einem Verfahren erhalten worden ist, das umfaßt:
    i) die Umsetzung eines mit Natrium- oder Calciumcarbonat überbasisch gemachten Natrium- oder Calciumsulfonats, das 0,9 bis 10 Basenäquivalente pro kg aufweist, mit einem Phosphorsulfid, das in einem solchen Mengenanteil verwendet wird, daß das Molverhältnis von Phosphor zu Basenäquivalent des überbasisch gemachten Sulfonats 0,002 bis 0,15 beträgt; und
    ii) das Inkontaktbringen des erhaltenen Produkts mit mindestens einer Verbindung mit aktivem Wasserstoff, ausgewählt aus Wasser, den Alkoholen, Phenolen, Carbonsäuren, Säureestern, Mineralsäuren, Mineralbasen, Aminen, Amiden und Mercaptanen.
  7. Zusammensetzung nach Anspruch 6, dadurch gekennzeichnet, daß in der Stufe (i) das Phosphorsulfid ausgewählt wird aus der Gruppe P₄S₇, P₄S₉ und P₄S₁₀.
  8. Zusammensetzung nach einem der Ansprüche 6 und 7, dadurch gekennzeichnet, daß in der Stufe (i) als Phosphorsulfid P₄S₁₀ verwendet wird.
  9. Zusammensetzung nach einem der Ansprüche 6 bis 8, dadurch gekennzeichnet, daß in der Stufe (i) die Reaktion bei einem Druck zwischen Atmosphärendruck und 0,5 MPa und bei einer Temperatur von 60 bis 130°C durchgeführt wird.
  10. Zusammensetzung nach einem der Ansprüche 6 bis 9, dadurch gekennzeichnet, daß in der Stufe (ii) die Verbindung mit aktivem Wasserstoff ausgewählt wird aus Wasser, Methanol, Isopropanol, einem Phenol, Essigsäure, einem Dialkylphosphit, Borsäure, Phosphorsäure, Ammoniak, einem Amin, einem Amid, Dimercaptothiadiazol oder einem substituierten Dimercaptothiadiazol der Formel
    Figure imgb0007
     worin R steht für ein Wasserstoffatom, falls x = 1, oder für eine Kohlenwasserstoffgruppe, falls x = 1 bis 5.
  11. Zusammensetzung nach einem der Ansprüche 6 bis 10, dadurch gekennzeichnet, daß in der Stufe (ii) die Verbindung mit aktivem Wasserstoff in einer Menge von 0,1 bis 5 Mol pro Mol Phosphor, wie er in dem Phosphorsulfid enthalten ist, verwendet wird.
  12. Zusammensetzung nach einem der Ansprüche 6 bis 11, dadurch gekennzeichnet, daß in der Stufe (ii) das Inkonaktbringen mit der Verbindung mit aktivem Wasserstoff bei einem Druck zwischen Atmosphärendruck und 0,5 MPa und bei einer Temperatur von 60 bis 130°C durchgeführt wird.
  13. Zusammensetzung nach einem der Ansprüche 6 bis 12, dadurch gekennzeichnet, daß sie im Milieu eines zwischen 60 und 150°C siedenden Lösungsmittels hergestellt worden ist.
  14. Verwendung einer Zusammensetzung nach einem der Ansprüche 1 bis 5 als Additiv in einem Mineralöl oder synthetischen Öl oder in einem Schmierfett in einer Konzentration von 0,5 bis 20 Massenprozent.
  15. Verwendung einer Zusammensetzung nach einem der Ansprüche 6 bis 12 als Additiv in einem Mineralöl oder synthetischen Öl oder in einem Schmierfett in einer Konzentration von 0,5 bis 20 Massenprozent.
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FR2698019B1 (fr) * 1992-11-18 1995-02-24 Inst Francais Du Petrole Produits colloïdaux contenant du calcium et/ou du magnésium, ainsi que du bore et/ou du phosphore et/ou du soufre, leur préparation et leur utilisation comme additifs pour lubrifiants.
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FR2645168B1 (fr) 1993-02-05
FR2645168A1 (fr) 1990-10-05
JPH02286791A (ja) 1990-11-26
EP0390664A3 (en) 1990-12-12
EP0390664A2 (de) 1990-10-03
DK0390664T3 (da) 1993-12-06
DE69002511D1 (de) 1993-09-09
CA2013458C (fr) 2002-04-23
DE69002511T2 (de) 1993-11-18
CA2013458A1 (fr) 1990-09-30
JP2916644B2 (ja) 1999-07-05
ES2060085T3 (es) 1994-11-16
US5080812A (en) 1992-01-14

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