WO1990005768A1 - Purification d'agents de lubrification industriels - Google Patents

Purification d'agents de lubrification industriels Download PDF

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Publication number
WO1990005768A1
WO1990005768A1 PCT/SE1989/000677 SE8900677W WO9005768A1 WO 1990005768 A1 WO1990005768 A1 WO 1990005768A1 SE 8900677 W SE8900677 W SE 8900677W WO 9005768 A1 WO9005768 A1 WO 9005768A1
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WO
WIPO (PCT)
Prior art keywords
phase
lubricating
polymeric
polymer
cutting
Prior art date
Application number
PCT/SE1989/000677
Other languages
English (en)
Inventor
Gunnar STRÖM
Original Assignee
Pegasus Separation Ab
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pegasus Separation Ab filed Critical Pegasus Separation Ab
Priority to EP89912680A priority Critical patent/EP0451160B1/fr
Priority to DE68927180T priority patent/DE68927180T2/de
Publication of WO1990005768A1 publication Critical patent/WO1990005768A1/fr
Priority to FI912351A priority patent/FI105273B/fi
Priority to NO911912A priority patent/NO301080B1/no
Priority to DK095591A priority patent/DK95591A/da

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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M175/00—Working-up used lubricants to recover useful products ; Cleaning
    • C10M175/04—Working-up used lubricants to recover useful products ; Cleaning aqueous emulsion based
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M125/00—Lubricating compositions characterised by the additive being an inorganic material
    • C10M125/24—Compounds containing phosphorus, arsenic or antimony
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C10M173/02—Lubricating compositions containing more than 10% water not containing mineral or fatty oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/081—Inorganic acids or salts thereof containing halogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/082—Inorganic acids or salts thereof containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/08—Inorganic acids or salts thereof
    • C10M2201/084—Inorganic acids or salts thereof containing sulfur, selenium or tellurium
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/085—Phosphorus oxides, acids or salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C10M2209/1045—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
    • C10M2209/1065—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • C10M2209/1075—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106 used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
    • C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
    • C10M2209/1095—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified used as base material
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • the present invention relates to the technical field industrial lubricating and/or cooling agents, especially su agents for use in metal working. More specifically the inve tion relates to purification of such agents, in the followi referred to as "lubricating agents", as regards microbi contaminants by using polymeric two-phase systems.
  • Cutting oils and cutting liquids represent a common ty of industrial lubricating agents which are widely used in t engineering industry in connection with cutting, turnin drilling, grinding and similar machining of materials. The primary function is to increase the useful life of the too by acting as a cooling and lubricating agent between t tools and the work pieces.
  • Cutting oils - as well as lubric ting agents in general - consist of. so-called base oil which may be based on mineral oils or be synthetic or sem synthetic.
  • Cutting liquids contain a plurality of components, fr bactericidal preparations to anti-foam agents and corrosi inhibitors.
  • fr bactericidal preparations to anti-foam agents and corrosi inhibitors Several of these components, together with micro-flora of bacteria and fungi, are considered to capable of causing problems, especially eczema and sk irriation, for industrial workers (Wahlberg, J.E. 1976, Ski influence of oil, Esso Symposium 1976).
  • Microbial growth in cutting liquids is thus a grea problem in today's engineering industry and there is a grea need of means for extending the useful 'life of cutting li quids. It may as an example be mentioned, that about 10,00 tons of cutting liquids in 1977 were used only in Sweden, o which about 2,000 tons were emulsion concentrates (LO: Report on Cutting Oils). The costs for the acquisition an disposal were estimated to be of the order of 140 to 20 millions SEK, to which should be added the far higher cost for shut-down in connection with the exchange of cuttin liquid.
  • JP 51079959 disclose an agent for the treatment of contaminated waste water including used cutting oil, by adsorption of the contami nants.
  • the adsorbent consists of very small complex bodie comprising inorganic particles and an organic polymer. Th inorganic particles may consist of active carbon or certai metal hydroxides.
  • Aqueous polymeric two-phase systems as such have bee known for a long time and have been used in laboratories fo biochemical and microbiological analyses and separations e.g. for separating macro molecules, cell particles and whol cells (e.g. Albertsson P. . 1960, Partition of Cell Particle and Macromolecules, 2nd edition, Almquist & Wiksell, Uppsal Blomquist G. and Strom G. 1984, The Distribution of Mou Fungi Conidies in Polymeric Two-Phase Systems, Work a Health No. 31, Strom G. 1986, Qualitative and Quantitati Analysis of Microorganisms Particularly Fungal Spore Methodological Developments, doctor's thesis, University Umea).
  • polymeric two-phase system have found f technical uses.
  • Polymeric two-phase systems substantially consist two aqueous solutions of polymers having different molecul weights. When the two polymer solutions are mixed in certa proportions, two immiscible aqueous phases are formed. T top-phase substantially contains the low molecular polym and the bottom-phase substantially contains the high molec lar polymer. The water contents in the systems is hig usually between 80-98% depending on. the choice of the pha polymers.
  • a suitable wate soluble salt e.g. phosphate buffer.
  • particles or cells a distributed substantially between the top-phase, the inte phase (the interface between the phases) and the botto phase; soluble macromolecules will be distributed between t top and bottom-phases.
  • top-phase component a “bottom-phase component” respectively when referring to thos component/components of the polymeric system, which aft mixing and separation of the system substantially are fou in the top-phase and the bottom-phase respectively.
  • the present invention aims at reducing or eliminatin the above mentioned problems and draw-backs of the prior ar systems for using, handling and getting rid of feature lubricating agents, in particular cutting liquids in th engineering industry.
  • a special object of the invention is to provide lubri eating agent/cutting liquid systems having a considerabl longer . seful life than today's systems.
  • Another special object of the invention is to provide purification process which makes it possible to purify lubri eating liquids microbially while in use, thereby considerabl reducing the shut-down time because of change of liquid.
  • a further object of the invention is to provide purifi cation methods and means for lubricating liquids which mee high demands on industrial hygien and working environment.
  • a still further object of the invention is to provide a improved analysis method for determining the contents o microbial contaminants in industrial lubricating agents, especially cutting liquids.
  • a further object of the invention is to provide a lubri eating agent which is also capable of serving as the top phase polymer in a polymeric two-phase system for separatin microbial contaminants from a lubricating agent.
  • the invention in it different aspects is founded on the basic concept of utili zing polymeric two-phase systems for separating microbia contaminants from contaminated lubricating agents.
  • the polymeric two-phase system wil be designed in such a manner that there is formed, afte mixing with a lubricating agent and phase separation, a top phase containing lubricant and a bottom-phase containing a least part, of the microbial contaminants, so that at least major part of the microbial contaminants can be remove together with the bottom-phase, which can easily be separate from the top-phase.
  • One aspect of the invention comprises a method of pur fying microbially contaminated lubricating agents, which characterized by the steps of mixing the lubricating age with a polymeric two-phase system, allowing the mixture separate so as to form a top-phase containg the lubricati liquid and a bottom-phase containing at least a part of t microbial contaminants, and separating at least a major pa of the microbially enriched bottom-phase from the top-phase.
  • Another aspect of the invention consists of a plant fo microbial purification of lubricating liquids.
  • This plant i characterized in that it comprises a mixing tank having mean for feeding microbially contaminated lubricating liquid t the mixing tank, means for feeding at least one of the com ponents of a polymeric two-phase system to the mixing tank at least one stirrer in the mixing tank, means for feedin the mixture to a separation device for separating the mixtur into a top-phase containing lubricating agent and a bottom phase containing microbial contaminants, and means for recir culation of the top-phase of the two-phase system.
  • a further aspect of- the invention consists of a ne lubricating oil concentrate which comprises lubricating oi and optionally conventional additives for lubricating oil and which is characterized in that at least part of th lubricating oil also is included in the top-phase componen of a polymeric two-phase system.
  • a further aspect of the invention relates to a ne cutting liquid which is characterized in that it consists o an aqeuous emulsion of the cutting oil concentrate accordin to the invention.
  • Figure 1 is a schematic presentation of a plant accor ding to the invention adapted for cleaning of mold cutting liquids, wherein the dashed lines illustrate alterna tive embodiments;
  • Figure 2 is a diagram showing the results of comparativ tests concerning the effect of cutting liquids on the usefu life of twist drilling tools. Description of Preferred Embodiments
  • the enclosed drawing schematically shows a purificatio plant illustrating how the principle of the cutting liqui cleaning according to the invention may be put into practice
  • the plant comprises a tank 1 for cutting liquid S containin the top-phase component.
  • the cutting liquid S is continuousl being circulated between the tank 1 and work stations (no shown) through inlet conduits 2 and outlet conduits 3 of th tank ' .
  • Suitable distribution conduits, pumps, etc. are use for transporting cutting liquid to and from the work sta tions. This is quite conventional technique and will there fore not be described further in this context.
  • the plant comprises a mixin tank 4, in which there is a stirrer 5, and a separator 6.
  • conduit 7, in which there is a shut-off valve 8, inter connects the cutting liquid tank S. with the mixing tank 4
  • the latter can also be connected to the separator 6 through conduit 9 having a shut-off valve 10.
  • a supply container 11 for fresh or recovered bottom-phas component and a collection container 12 for- used bottom phase The supply container 11 is connected to the mixin tank 4 through a conduit 13, and a conduit 14 interconnect the collection container 12 with the bottom part of th separator 6.
  • Fresh bottom-phase component can be supplied t the supply container 11 from a supply (not shown) through conduit having a valve 15.
  • An interconnecting conduit 1 makes it possible, if desired, to re-use bottom-phase fro the container 12 through a (dash-dotted) conduit 16, whic may have a suitable rough filter 17.
  • a return conduit 1 returns purified cutting liquid to the tank 1.
  • the described plant ca be used i.a. as follows for purifying microbially contamina ted cutting oil circulating through the tank 1. It should i this context especially be noticed that the cleaning can b carried out without any need of interruping the feeding o cutting liquid to the work stations; this means that th circulationg of cutting liquid through the conduits 2 and may continue as usual.
  • Contaminated cutting liquid S is supplied to the mixi tank 4 by opening the valve 8 in the conduit 7.
  • Fresh or r used bottom-phase is supplied to the mixing tank 4 throu the conduit 13. The supply valves are then closed and top ' a bottom-phase components are mixed with the contaminat cutting liquid.
  • valve 10 opened and the mixture is transferred to the separator wherein it is allowed to separate into a top-phase T and bottom-phase B.
  • the purified to phase will be returned to the cutting oil tank 1 through t conduit 18.
  • the bottom-phase B together with its microbi contaminants will be discharged through the bottom condu 14.
  • the bottom-phase B can either be discarded through drain 19 or be returned to the tank 11, preferably aft rough filtering and/or other purification in the devi generally designated 17.
  • Disposal is preferred when t bottom-phase component consists of cheap material, where re-use is preferable when it contains expensive material su as fractionated dextran.
  • the re-circulated to phase will also contain a minor amount of the correspondi salt.
  • Such salts may have an unfavourable effect on t properties of the cutting liquid, and it is then preferab to desalt the top-phase before returning it into the tank
  • the plant shown in the drawing has be provided with a desalting device 20, which may be based desalting principles which are known per se.
  • Top-phase polymers which are preferred according to t invention are comparatively low molecular hydrophilic pol mers, especially polymers which are not solid at room te perature.
  • hydrophilic polymers of higher molecul weight which are solid at room temperature
  • solvent By the addition of solvent it can b achieved that the cutting liquid will not leave any soli residue on evaporation; such a residue may have a detrimenta effect on the utility of the lubricating liquid by leaving hard crust on the machines.
  • the top-phase component of th two-phase system comprises at least one polyalkylene glycol especially a polyethylene glycol having an average molecula weight of 200-20,000, especially 400-10,000, in particula about 600-4,000.
  • it is advan tageous to use, as the top-phase, also other hydrophili polymers which are liquid at room temperature and/or at th temperature of use and which per se are useful in syntheti cutting oils as the single cutting oil component or togethe with other cutting oil components in synthetic or semi-syn thetic cutting oils.
  • Polyoxyalkylene-polyalcohol ethers suc as polyoxyalkyleneglycol ethers, linear polymers of ethylen and/or propylene oxide are a few examples of preferred poly mers, which are capable of simultaneously functioning as cutting liquid and a top-phase component.
  • Such lubricatin liquids may, for example, contain at least about 2% by weight, especially at least 4, often at least 6% by weigh of the polymer, especially at least 7% by weight.
  • the concentration of the top-phase polymer in the lubricating liquid decreases with increasing molecu lar weight.
  • the bottom-phase com ponent contains a polymer
  • such polymer preferably has higher average molecular weight than the top-phase polymer
  • the bottom-phase polymer preferably has an average molecula weight of at least 40 ⁇ 000.
  • it* is preferably cross-linked
  • suitable bottom-phase polymers are polysacchari des, in raw or refined form, especially cross-linked poly saccharides, in particular cross-linked dextran, starch cellulose, polyglucose or cross-linked mono-, di- or olig saccha.rides.
  • suitable bottom-pha polymers are polyvinyl alcohols of different average molec lar weights. Polyvinyl alcohols can be recovered from t bottom-phase by e.g. precipitation.
  • the bottom-phase component may also advantageous comprise a small amount of a suitable agent distributi into the bottom-phase and promoting the transfer of t microbial contaminants from the top-phase to the botto phase.
  • a suitable agent preferably carry positive electric charg which attract the negative charges on the cell surfaces the bacteria.
  • the system is preferably kept a pH from neutral to slightly basic so as to expose t charges on the cell surfaces of the bacteria.
  • charge-exposing agents are hydrophilic polymers co taining positively charged groups,, e.g. DEAE-groups.
  • Su positively charged agents may be present in very low co centrations (the order of magnitude of 10 ⁇ 2% - 10 _3 %) a still have a strong effect.
  • these salts may e.g. consist of common buff salts suf as alkali metal phosphates and sulphates and mi tures thereof.
  • the amounts of such salts may vary within co paratively broad limits, the amount i.a. depending ' on t particular salts and the particular top-phase polymer bei used. For example, good results are obtained when using two-phase system comprising phosphate buffer in combinati with low molecular polyetheylene glycol, about 10-20% of ea component.
  • the lubricating liquids according to the inventi preferably comprise 1-16% by weight of lubricating oi especially about 2-10% by weight of lubricating oil, at lea about 2% by weight of top-phase component, especially least about 4% by weight of top-phase component, and when t top-phase component comprises a low molecular polymer whi is not solid at room temperature, preferably at least abo 8% by weight of the top-phase component, the remainder esse tially consisting of water.
  • the upper limit for the amount o top-phase component is not particularly critical and wil therefore primarily be chosen with regard to practical/econo mical considerations.
  • polymeric two phase systems for separating microbial contaminants fro contaminated lubricating liquids can also preferably be use for analysing the separated phase with regard to microbia contaminants.
  • Such an analysis which preferably will b performed substantially quantitatively or semi-quantitative ly, gives a very rapid and reliable basis for judging th quality of the lubricating liquid and as a guide for deter mining what measures may be necessary to take, for exampl addition of biocide ⁇ , exchange of lubricating liquid, etc.
  • a present such analyses are performed by cultivation on suit able nutritions substrates, usually having the form of "sticks" to be dipped into the lubricating liquid. The cul tivation requires several days to be completed and the erro margins are considerable.
  • the bottom-phase which is separated in the purificatio method for cutting oils according to the invention can b used for the analysis, but it is preferred to take a specia sample for the analysis.
  • the bottom-phase it is preferre to use salts of the above indicated type instead of hig molecular polymers.
  • salts of the above indicated type instead of hig molecular polymers.
  • the starting point for the use of two-phase technique for continuous purification of cutti liquids is that addition of cutting oil/emulsion concentrat to a two-phase system provides a top-phase in the nature e.g. a cutting liquid/polymer phase which is well separat from a bottom-phase which collects microbial contaminant
  • a top-phase in the nature e.g. a cutting liquid/polymer phase which is well separat from a bottom-phase which collects microbial contaminant
  • factors which may influence the distribution a microbial particle between the top, inter and bottom-phas are, for example, the choice of polymers' - charged/uncharg polymers - the polymer concentration, the choice of pH a the ionic strength.
  • the machining test was performed using production machi ning data on heat treatment steel (SS 2541-03) and a stabl machine tool.
  • Tool material High speed steel, SIS 2724, ⁇ 6 mm
  • the work pieces are taken from one charge and are rolle in sequence. They are cut to a size of 200 x 30 x.375 m (about 400 bores/plate) and spot faced.
  • the tools are normalized with narrow geometric toleran ces and hardness variations.
  • the work pieces (2) are clamped into the machine and th test program is designed so as to distribute the machining both plates for each tool, the purpose being to avoid lo unevenness in the material.
  • the cutting speed is varied f different drills in order to obtain a relation between cu ting speed and warn-out time (vT-curve).
  • Destruction of the tool is seen as vibrations and changing cuttings (the tip melts). This occurs within a f seconds.
  • Liquid 1 has a turbid border zone, rough emulsio but the border zone is clear for Liquid 2.
  • An important property for the useful life of a cutti liquid is the capability of efficiently separating contamin ting leak oil from i.a. hydraulic systems.
  • the cutting liquid according the invention had an evident anti-corrosive effect on cas iron whereas the effect of the reference liquid was unacce table for engineering products. Both products showed increased effect on steel.
  • Amine derivatives are often used as corrosion inhibito in cutting liquids. These amines often cause working enviro mental problems. Furthermore, carbon/nitrogen compounds the amine type can readily be used as a substrate by micr organism, thereby promoting the microbial growth. The evide corrosion inhibiting effect when adding a top-phase polym according to the invention can make it possible to complete exclude amine compounds from these products.
  • Hard crystalline evaporation residues from a cuttin liquid may have a negative effect on movable machine par and precision tools.
  • the evaporation tests with the miner oil based fine emulsion with addition of polymer according the invention showed that the product could not be evapora ted, probably because a formed surface layer prevented wate from escaping.
  • Other evaporation tests using both mineral oi based and semi-synthetic emulsion concentrates containin polymer according to the invention and water showed that n hard crystalline evaporation residue was formed.
  • two-phases were ob tained, one consisting of concentrate and the other of th added top-phase polymer.
  • the final concentration in the system was 0.001% fo DEAE-dextran and 1% for the other polymers (w/w) .
  • the quantification of the number of fungi, elements wa performed by cultivation on a substrate composed of 2% (w/w of malt extract (Oxoid, L 39), 1.5% Agar (Oxoid, L 28) and 3 mg/1 of streptomycin sulphate (Sigma Chemical Co.). Incuba tion was carried out at room temperature (22°C) during days, after which the number of colony forming units could b determined.
  • the concentration of bacteria was determined by th cultivation on a substrate composed of 2.4% (w/w) Trypto Glucose Extract Agar (CM 127, Oxoid), 0.2% Casein Hydrolysa (Acid) (L 41, Oxoid) and 50 mg/1 Actidione (Sigma).
  • the number of colony forming units was determined aft incubation for six days at room temperature.
  • a semi-synthetic fine emulsion was us together with the top-phase polymers (Table 1), and in t other case a mineral oil based rough emulsion (Table 2 Together with the bottom-phase polymers also diethylamin ethyl-dextran (DEAE-dextran) was added to a final concentr tion of 0.001%.
  • top-phas polymers according to the invention with excellent result can be included in cutting liquids and at the same tim function as the top-phase in a two-phase system for microbia cleaning of the cutting liquid.
  • dextran As regards dextran, a broad range of fractions, fro finely fractioned Dextran 500 (molecular weight 500,000) t more unfractionated (and consequently cheaper) raw dextra have been tested and found to be very useful.
  • hig molecular dextran it has been found to be especially adva tageous with a top-phase concentration of about 19% (w/w) Polyethylene glycol 600 or, alternatively, about 12.5% Pol ethylene glycol 600 + 2.5% Polyethylene glycol 8000. In ' t latter case it is suitable to use a semi-synthetic cutti liquid concentrate.
  • dextran When purifying these systems the amount of dextran m be about 1%, resulting in a bottom-phase volume making about 3-5% of the total system.
  • dextran may be replaced by other hi molecular polymers, e.g. soluble starch, glucogen or sy thetic polyglucose, as the bottom-phase polymer.
  • High molecular polyethylene glycols (mw > 1000), whi are crystalline at room temperature, are not* soluble in concentrate based on mineral oil only, but is highly solubl in synthetic emulsion concentrates. Evaporation tests using mixture of 2.5% (weight/weight) of Polyetheylene glycol 80O (Carbovax 6000), 5% (w/w) of semi-synthetic emulsion co centrate (fine emulsion), and 12.5% (w/w) of Polyethyle glycol 600 did not produce any crystalline residue.
  • the bottom-phase polymer may consis of unfractionated or substantially unfractionated raw dex tran.
  • raw dextran preferably has a molecular weight o 5-40 millions, and it is preferably used in mixture with small amount of positively charged polymer such as DEAE dextran.
  • Raw dextran is the presently preferred material fo the bottom-phase polymer since it is both cheap and effi cient. It is especially preferred to use raw dextran whic has been substituted with a small amount of positively char ged groups, e.g. DEAE groups, in which case it is not neces sary to add any separate charged polymer when there is a nee thereof.
  • raw fractions of other polysaccharides can b used in corresponding manner.
  • the polymer contents can be a low as . about 0.01%.
  • a synthetic cutting liquid was prepared by mixing th following components in water to the indicating concentra tions.
  • Emkarox VG 680W 6 % (a polyoxyalkylene glycol ether from ICI)
  • the utility of the obtained cutting liquid was tested i machining tests and was rated as category 2, which means hig class cutting liquid.
  • Bacterial cells and fungal spores were added (in th above described manner) to the above cutting liquid to simu late a microbially contaminated cutting liquid.
  • Raw dextra molecular weight 5-40 millions, final concentration 0.1% with added DEAE-dextran (final concentration 0.01%) was use as the bottom-phase polymer.
  • the top and bottom-phases were mixed and allowed to separate; 97-99% of the bacteria an about 99% ( of the fungi were transferred into the bottom-phas and separated.
  • a presently preferred embodiment of the analysis metho according to the invention for quantification of the mic bial contamination of cutting liquids will now be descri as an illustrative but non-limiting example.
  • the results the analysis can e.g. be used for judging the quality of used cutting liquid.
  • a pre-determined amount of a polymeric two-phase sys according to the invention was added to a test bottle havi a sealable, preferably "pipette shaped" stopper.
  • a bott holding a total of about 50 ml can e.g. be charged with 20 of the system in advance, sealed and delivered to the use
  • an aliquote (20 ml) of a cutting liqu sample is "pipetted" into the bottle, which is then shaken as to mix the phases and then allowed to separate with t bottle turned upside down.
  • the bottle may preferably be co pressible and have a suitable visible volume scale. T separation is normally very good . already after 10 to seconds, but it is preferred to allow the separation proceed for a few minutes.
  • t bottom-phase which substantially consists of salt solutio e.g. phosphate buffer pH aboi:-; 6.8 and comparison with standard curve for a corresp- ⁇ ding system, prepared in manner known per se.
  • t first step e.g. 10 ml of bottom-phase
  • a suitable polymer for a second pha system e.g. 4 g of polypropylene glycol having a molecul weight of about 425.
  • t bottom-phase from the first separation is located closest the opening of the bottle, which preferably is "pipette sh ped", the transfer and metering to the second system can done very conveniently. Also this second separation can carried out in a pre-prepared bottle designed similarly the first bottle.
  • the second bottle is shaken so as to m the phases well, then allowed to rest until the phases ha separated (normally the same separation times as for t first separation are preferred) , and a predetermined amoun of the biomass-enriched bottom-phase is taken out for tur bidimetric analysis and comparison with a standard curv (which expression also includes a specific mathematica relation or any other relation for quantification of th measured value which has been determined in advance) .
  • the sample may optionally be diluted with e.g particle-free water (in the given specific example e.g. 2 m sample plus 2 ml of particle-free water) .
  • th amount of live biomass can be determined in the above indi cated manner, e.g. by using fluorescinediacetate (FDA) as marker.
  • FDA fluorescinediacetate
  • the -separation method according to the invention ca also advantageously be used for making used cutting liquid or other lubricating liquids such as.waste oil disposable.
  • used cutting liquid or other lubricating liquids such as.waste oil disposable.
  • the disposal of e.g. synthetic or semi-syntheti cutting liquids is a very costly process because it is ver difficult to concentrate diluted polymer mixtures (and th polymer cannot be disposed of just anywhere) .
  • the disposa costs can often be as high as the purchase price.
  • this problem can be easily remided by strongly concentrating the polymer, e.g. in the followin way.
  • a used-up cutting liquid containing about 7 % by weigh of Emkarox (see above) as the top-phase polymer is mixed wit about 60% phosphate buffer (bottom-phase) to a final concen tration of 25% and allowed to separate (from a minute to a hour or so).
  • a very concentrated and easily separable polyme top-phase is formed (e.g. 35-50%, total volume about 5% o the cutting liquid volume), which can be destructed, wherea the aqueous phase usually can be disposed of directly.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Forging (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)

Abstract

L'invention concerne l'emploi de systèmes à deux phases permettant l'élimination de contaminants microbiens contenus dans des agents de lubrification industriels, ainsi qu'un procédé de purification d'agents de lubrification contaminés par des microbes, consistant à mélanger ledit agent de lubrification avec un système polymère à deux phases, à laisser le mélange se séparer de manière à former une phase supérieure contenant ledit agent de lubrification ainsi qu'une phase inférieure contenant au moins une partie des contaminants microbiens, puis à séparer de la phase supérieure au moins une grande partie de la phase inférieure à enrichissement microbien. L'invention concerne également une installation de purification microbienne d'agents de lubrification, comprenant un réservoir de mélange (4) dotés de moyens (7, 8) destinés à alimenter ledit réservoir de mélange en agent de lubrification (S) contaminé par des microbes, un moyen (13) acheminant dans ledit réservoir de mélange un système polymère à deux phases, un mélangeur-agitateur (5) situé dans ledit réservoir de mélange, des moyens (9, 10) destinés à acheminer le mélange dans un dispositif de séparation (6), afin de séparer ledit mélange en une phase supérieure (T) contenant des agents de lubrification, et en une phase inférieure (B) contenant des contaminants microbiens, ainsi qu'un moyen (18) permettant de récupérer la phase supérieure dudit système à deux phases, et un concentré d'agent de lubrification, dans lequel au moins une partie dudit agent de lubrification fait en même temps partie du constituant phase supérieure du système polymère à deux phases.
PCT/SE1989/000677 1988-11-21 1989-11-21 Purification d'agents de lubrification industriels WO1990005768A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP89912680A EP0451160B1 (fr) 1988-11-21 1989-11-21 Purification d'agents de lubrification industriels
DE68927180T DE68927180T2 (de) 1988-11-21 1989-11-21 Reinigung industrieller schmiermittel
FI912351A FI105273B (fi) 1988-11-21 1991-05-15 Menetelmä mikrobikontaminanttien poistamiseksi kontaminoituneista voiteluaineista
NO911912A NO301080B1 (no) 1988-11-21 1991-05-16 Fremgangsmåte for rensing av industrielle smöremidler
DK095591A DK95591A (da) 1988-11-21 1991-05-21 Rensning af industrielle smoeremidler

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8804206A SE462393B (sv) 1988-11-21 1988-11-21 Anvaendning av vattenhaltiga polymera tvaafassystem foer rening av skaervaetskor, foerfarande och anlaeggning foer reningen samt skaeroljekoncentrat innehaallande polymer ingaaende i tvaafassystemet och skaervaetska utgoerande vattenemulsion av skaeroljekoncentratet
SE8804206-4 1988-11-21

Publications (1)

Publication Number Publication Date
WO1990005768A1 true WO1990005768A1 (fr) 1990-05-31

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PCT/SE1989/000677 WO1990005768A1 (fr) 1988-11-21 1989-11-21 Purification d'agents de lubrification industriels

Country Status (11)

Country Link
EP (1) EP0451160B1 (fr)
JP (1) JP2983235B2 (fr)
AT (1) ATE142685T1 (fr)
AU (1) AU645004B2 (fr)
DE (1) DE68927180T2 (fr)
DK (1) DK95591A (fr)
ES (1) ES2091767T3 (fr)
FI (1) FI105273B (fr)
NO (1) NO301080B1 (fr)
SE (1) SE462393B (fr)
WO (1) WO1990005768A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995003866A1 (fr) * 1993-07-30 1995-02-09 E.I. Du Pont De Nemours And Company Appareil de separation de liquides multi-phases a contre-courant
WO1995014752A1 (fr) * 1993-11-29 1995-06-01 Kemisk Separering Tumba Aktiebolag Purification d'huile
WO1995032304A1 (fr) * 1994-05-23 1995-11-30 E.I. Du Pont De Nemours And Company Procede de separation rapide et d'identification de contaminants microbiens depuis une matrice complexe

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE9303437D0 (sv) * 1993-10-18 1993-10-18 Pegasus Separation Ab Reningsförfarande

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DERWENT'S ABSTRACT, No. 76- 65 593/35, JP 51 079 959, publ. week 7635 (MITSUBISHI RAYON KK) *
G. BLOMQUIST et al."FORDELNING AV MOGELSVAMPSKONIDIER I POLYMERA TVAFASSYSTEM", 1984, ISBN 91-7464-224-3 ISSN 0346-7821, Umea, *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995003866A1 (fr) * 1993-07-30 1995-02-09 E.I. Du Pont De Nemours And Company Appareil de separation de liquides multi-phases a contre-courant
US5578201A (en) * 1993-07-30 1996-11-26 E. I. Du Pont De Nemours And Company Apparatus for mixing liquids used in countercurrent multiphase liquid separation
WO1995014752A1 (fr) * 1993-11-29 1995-06-01 Kemisk Separering Tumba Aktiebolag Purification d'huile
US5976357A (en) * 1993-11-29 1999-11-02 Alfa Laval Separation Ab Purification of oil
WO1995032304A1 (fr) * 1994-05-23 1995-11-30 E.I. Du Pont De Nemours And Company Procede de separation rapide et d'identification de contaminants microbiens depuis une matrice complexe

Also Published As

Publication number Publication date
AU4519789A (en) 1990-06-12
DE68927180T2 (de) 1997-02-20
SE8804206D0 (sv) 1988-11-21
DK95591A (da) 1991-07-09
EP0451160B1 (fr) 1996-09-11
FI912351A0 (fi) 1991-05-15
DK95591D0 (da) 1991-05-21
JP2983235B2 (ja) 1999-11-29
DE68927180D1 (de) 1996-10-17
AU645004B2 (en) 1994-01-06
JPH04501731A (ja) 1992-03-26
ATE142685T1 (de) 1996-09-15
FI105273B (fi) 2000-07-14
NO301080B1 (no) 1997-09-08
NO911912L (no) 1991-05-16
ES2091767T3 (es) 1996-11-16
EP0451160A1 (fr) 1991-10-16
SE462393B (sv) 1990-06-18
NO911912D0 (no) 1991-05-16

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