Classifications

• • 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
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
  • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
  • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
  • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
  • H01B3/20—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils
  • H01B3/24—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances liquids, e.g. oils containing halogen in the molecules, e.g. halogenated 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
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/026—Butene
• • 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
  • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
  • C10M2209/084—Acrylate; Methacrylate
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
  • C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
• • 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
  • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
  • C10M2211/06—Perfluorinated compounds
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
  • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/08—Amides
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/08—Amides
  • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/26—Amines
• • 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
  • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
  • C10M2215/28—Amides; Imides
• • 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
  • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
  • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
  • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral 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
  • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
  • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
  • C10M2223/04—Phosphate esters
  • C10M2223/041—Triaryl phosphates
• • 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
  • C10N2010/00—Metal present as such or in compounds
  • C10N2010/04—Groups 2 or 12
• • 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/16—Dielectric; Insulating oil or insulators
• • 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
  • C10N2040/14—Electric or magnetic purposes
  • C10N2040/17—Electric or magnetic purposes for electric contacts

Definitions

• the invention relates to a flame-retardant, biodegradable functional fluid, in particular a hydraulic fluid or an insulation fluid for electrical devices, which contains a bromine-containing benzyltoluene derivative and conventional additives as an essential component.
• Chlorinated aromatics especially chlorinated biphenyls
• the polychlorinated biphenyls have been widely used as hydraulic fluids, as insulation fluids for electrical systems, and as flame retardant additives for plastics and the like.
• these connections have been badly discredited.
• Serious health and environmental effects of these products have been identified, and catastrophic hazards are possible if there is a fire, since highly toxic dioxins and dibenzofurans can be formed. This has resulted in the fact that the production or at least the use of such compounds has already been completely banned by the state supervisory bodies and that severe restrictions have been imposed on the use of these substances.
• EP-A-88 650 proposes to use chlorinated benzyltoluenes and chlorinated benzyloxylols as lubricants, which can also be used as hydraulic fluids, since these compounds are flame-retardant and resistant to oxidation and are also biodegradable and with regard to them toxic behavior should have advantages.
• GB-A-1 504 655 describes electrical devices which contain readily biodegradable dielectric liquids, namely halogenated diphenylmethanes, which are characterized in that the halogen substituents and any alkyl substituents are only present in one of the two phenyl rings, while the other phenyl ring must be unsubstituted , since it is stated that only those halogenated diphenylmethanes which have an unsubstituted phenyl group can readily be biodegraded, while the diphenylmethanes substituted on both phenyl radicals are intended to resist microbiological degradation.
• EP-A-8 251 discloses liquid dielectrics which can be used, for example, as insulating liquids for transformers or as impregnating agents for capacitor insulator layers. These are essentially chlorinated alkylaromatic compounds which have been obtained starting from chlorotoluene and / or chloroxylene, such as, for example, tetrachlorobenzyltoluene, which are said to have advantages over the polychlorinated biphenyls hitherto used for the same purpose. The absence of the biphenyl nuclei and the presence of the alkyl groups on the aromatic nuclei are assigned a favorable effect on the biodegradation behavior.
• EP-A-71 338 or the corresponding GB-A-2 100 740 describes electroviscous liquids which are present in the form of suspensions of finely divided hydrophilic solids in hydrophobic liquids. These electroviscous fluids are used in electronically controlled hydraulic devices. When an electric field is applied to such a suspension, the viscosity of this mixture increases drastically. The change is reversible and fast, so that such suspensions can be used, for example, in electronically controllable clutches. It is stated that the hydrophobic liquid present in the mixture has a high boiling point, a low viscosity, sufficient electrical properties, is chemically stable and, moreover, has low toxicity and should preferably be biodegradable.
• halogenated diaryl derivatives are used as hydrophobic liquids, the aromatic nuclei of which are connected to one another by a wide variety of bridges and may have fluorine, chlorine or bromine atoms as halogen substituents.
• the very general formula given for these diaryl derivatives includes a wide variety of compounds.
• asymmetrically substituted diaryl derivatives are preferred because the asymmetry in the molecule is said to promote biodegradability.
• the object of the present invention is to provide functional liquids which have all the physical properties necessary for the intended application and which can be biodegraded at the same time with high chemical stability, are largely non-toxic and do not become highly toxic products, such as dioxins, even if handled improperly , to lead.
• the invention therefore relates to the flame-retardant, biodegradable, functional liquid according to the patent claim.
• the invention therefore relates to a flame-retardant, biodegradable functional liquid. containing at least one bromine-containing benzyltoluene derivative and conventional additives, which is characterized in that it contains dibromobenzyltoluene of the formula (I) as the bromine-containing benzyltoluene derivative and or
• Monobromxylylxylene of formula (11) contains in an amount of at least 35 wt .-%.
• the bromine-containing benzyltoluene derivatives used as or in functional liquids according to the invention are therefore compounds which are substituted on both nuclei, at least one bromine substituent and one methyl group having to be present as a substituent.
• the positions of these substituents are not essential, so that, according to the invention, all positional isomers of these bromine-containing benzyltoluene derivatives of the above general formulas I and 11 can also be used in or as functional liquids.
• bromine-containing benzyltoluene derivatives used according to the invention have a considerably more favorable environmental compatibility than the halogenated diaryl derivatives known from the prior art, and at the same time have excellent physical properties which are particularly suitable for functional liquids, such as hydraulic liquids or insulation liquids for electrical devices make well suited.
• bromine-containing benzyltoluene derivatives of the general formulas I and II given above which are substituted on both phenyl rings and which are used according to the invention can readily be biodegraded, which in view of the EP-A-71 338 referred to above GB-A-2 100 740 and GB-A-1 504 655 can be regarded as surprising.
• these bromine-containing benzyltoluene derivatives of the above general formulas used according to the invention have the further surprising advantage that they are liquid under normal conditions of use and have a particularly favorable viscosity-temperature behavior.
• the functional liquids according to the invention can of course contain the bromine-containing benzyltoluene derivatives defined above individually, but preferably in the form of mixtures, especially in the form of mixtures of the individual positional isomers of these compounds.
• the compounds of the above general formulas selected and used according to the invention differ from the biodegradable bromine-containing benzyltoluene derivatives described in GB-A-1 504 655 in that they are not asymmetrical but are substituted on both phenyl rings and nevertheless have surprisingly advantageous properties .
• the bromine-containing benzyltoluene derivatives used according to the invention are prepared in a manner known per se either by halogenating the corresponding non-halogen-substituted benzyltoluenes with elemental bromine in the presence of a known halogenation catalyst such as iron, FeCl 3 , FeBr 3 , AICI 3 , TiC1 4 and the like.
• a known halogenation catalyst such as iron, FeCl 3 , FeBr 3 , AICI 3 , TiC1 4 and the like.
• the reaction can be carried out at room temperature, but depending on the particular catalyst, temperatures between -5 and + 40 ° C. are also suitable.
• Hal is bromine or chlorine and x is 1 and z is 0 or 1.
• the condensation is carried out, if appropriate, in the presence of a Friedel-Crafts catalyst, such as FeCl 3 , FeBr 3 , AICI 3 and / or TiCl 4 , with an excess of compounds of the general formula III.
• a Friedel-Crafts catalyst such as FeCl 3 , FeBr 3 , AICI 3 and / or TiCl 4
• the bromine-containing benzyltoluene derivatives used according to the invention show a substantially improved flame retardancy with a simultaneously improved viscosity-temperature behavior.
• the asymmetrically substituted dibromobenzyltoluene known from GB-A-1 504 655 solidifies at room temperature, while the isomer brominated on both phenyl rings only solidifies at -25 ° C., which is particularly advantageous for the use of this compound as a hydraulic fluid or insulating fluid.
• the bromine-containing benzyltoluene derivatives used according to the invention have proven themselves not only in the case of hydraulic liquids but also in the case of insulation liquids for electrical devices, such as, for example, capacitors, transformers and the like, not only because of their favorable viscosity-temperature behavior but also because of their very favorable flame-retardant effect.
• the functional fluids according to the invention can therefore in particular also be used as flame-retardant hydraulic fluids or flame-retardant insulation fluids which, because of their low toxicity, their low tendency to form toxic decomposition products and their biodegradability, represent a considerable enrichment of technology.
• the bromine-containing benzyltoluene derivatives mentioned may be present individually or in the form of mixtures, especially in the form of the isomer mixtures.
• bromination of toluene with elemental bromine is first carried out in the presence of anhydrous FeC1 3 bromotoluene, which is then brominated on the side chain.
• anhydrous FeC1 3 bromotoluene which is then brominated on the side chain.
• 8.3 mol of bromotoluene are heated in the presence of 0.5 g of a radical chain initiator (a, a'-azobisisobutyronitrile) to a temperature of 80 ° C. 1.66 is dripped in under irradiation with an ultraviolet lamp with an output of 300 W. Moles of bromine with cooling.
• the resulting hydrogen bromide is absorbed in a wash bottle with chilled water.
• the cooled mixture is then added dropwise to a condensation reaction in a suspension of 6 g FeCl 3 in 1.66 mol bromotoluene at a temperature of 30 ° C.
• the resulting gaseous hydrogen bromide is absorbed in the same way as described above with chilled water in a wash bottle.
• this condensation reaction the formation of by-products (brominated dibenzyltoluene) is suppressed by the large excess of bromotoluene used.
• the mixture is heated to 50 ° C. for 30 minutes, whereupon the cooled reaction mixture is mixed with 1 liter of water and then with 1 liter of 10% strength Sodium hydroxide solution and then washed again with 1 liter of water.
• the organic phase is dried and the excess bromotoluene is distilled off.
• the remaining liquid is rectified at 0.4 mbar, giving 395 g of a main fraction boiling between 155 and 166 ° C. at 0.4 mbar, which is identified by mass spectrometry as dibromobenzyltoluene. An isomer investigation was not carried out.
• the following table shows the electron current mass spectrum of the dibromobenzyltoluene obtained.
• bromine-containing benzyltoluene derivatives used according to the invention are obtained in an analogous manner to the procedure described above using methods known per se or also by direct bromination or bromination and chlorination of benzyltoluene, in which case, however Reaction mixtures are obtained which have to be separated in a suitable manner, for example by gas chromatography, into the bromine-containing benzyltoluene derivatives of the general formulas given above used according to the invention.
• the flame-retardant, biodegradable functional liquids according to the invention can also contain additional constituents and additives customary for the functional liquids, for example corrosion inhibitors, such as alkaline earth metal sulfonates, stabilizers, such as amine derivatives or phenolic products, wear-reducing additives, for example zinc dialkylditheakophosphates, for example epoxy compounds, tetraphenyltin, etc., and also defoamers, such as soap, silicones, glycols, phosphate esters, and viscosity index improvers, such as polymethacrylates, polyisobutylene.
• the bromine-containing benzyltoluene derivatives used according to the invention can be modified with many suitable products, such as mineral oil, glycols, etc.
• the biodegradability is examined with the aid of a recognized measuring method for determining the biodegradability of anionic and nonionic synthetic surfactants, namely the OECD screening test (Federal Law Gazette 1 (1977), page 245) (modified) for nonionic surfactants.
• Aerobic, polyvalent microorganisms from the drain of a biological sewage treatment plant are used as the vaccine suspension.
• the first sample is taken after 7 days, the second sample after 14 days and the third sample after 19 days.
• the samples taken were processed in accordance with the instructions of the test described above and the rate of degradation was determined by gas chromatography.
• the fire test is carried out according to the "6th Switzerland report on requirements and tests of flame-retardant liquids for hydraulic power transmission and control".
• dibromobenzyltoluene exhibits better fire behavior than, for example, tetrachlorobenzyltoluene or polychlorinated biphenyl.
• dibromobenzyltoluene The corrosion effect of dibromobenzyltoluene was investigated using the method of the 6th Luxembourg report mentioned above. For this purpose, two-thirds of the metals steel, copper, brass, aluminum, cadmium and zinc and the metal pairings copper-zinc, steel-aluminum, steel-cadmium and aluminum-zinc were immersed in the liquid to be tested (dibromobenzyltoluene) and in it for 28 days leave at a temperature of 35 ° C.
• a sealing element made of the sealing material 83 FKM 575 (Viton) is immersed in the liquid to be examined, for 21 days at 60 ° C, 80 ° C, 100 ° C, 120 ° C and 150 ° C . The change in volume of the sealing element and the change in its Shore hardness are then determined.
• the bromine-containing benzyltoluene derivative namely dibromobenzyltoluene, which is preferably used according to the invention, exhibits particularly good behavior as such and also in fully formulated hydraulic fluids, in that the volume change of the sealing material moves between ⁇ 1 and 2% and the change in the Shore hardness contributes -3 degrees.
• a change in volume of up to 20% and a change in Shore hardness of -10 degrees are permitted.
• the investigated comparative products based on polychlorinated biphenyl and tetrachlorobenzyltoluene show volume change values of 40% at an investigation temperature of 150 ° C.
• dibromobenzyltoluene was pyrolyzed at temperatures between 150 and 700 ° C.
• the sample is processed according to EPA method no. 613.
• no highly toxic dioxin or dibenzofuran was found within the detection limit (0.5 ppb).

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• Chemical & Material Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Purses, Travelling Bags, Baskets, Or Suitcases (AREA)
• Measurement And Recording Of Electrical Phenomena And Electrical Characteristics Of The Living Body (AREA)
• Fireproofing Substances (AREA)
• Biological Depolymerization Polymers (AREA)
• Materials For Medical Uses (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Medicines Containing Material From Animals Or Micro-Organisms (AREA)
• Organic Insulating Materials (AREA)
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• 1984
  • 1984-01-27 DE DE19843402863 patent/DE3402863A1/de not_active Withdrawn
• 1985
  • 1985-01-25 JP JP60500653A patent/JPS61501035A/ja active Pending
  • 1985-01-25 DE DE8585100772T patent/DE3570692D1/de not_active Expired
  • 1985-01-25 WO PCT/DE1985/000020 patent/WO1985003306A1/de active IP Right Grant
  • 1985-01-25 HU HU851051A patent/HU194300B/hu not_active IP Right Cessation
  • 1985-01-25 AT AT85100772T patent/ATE43628T1/de not_active IP Right Cessation
  • 1985-01-25 EP EP85100772A patent/EP0150826B1/de not_active Expired
  • 1985-01-25 AU AU39308/85A patent/AU573782B2/en not_active Ceased
  • 1985-01-28 CA CA000472977A patent/CA1244054A/en not_active Expired
  • 1985-01-28 ZA ZA85638A patent/ZA85638B/xx unknown
  • 1985-09-16 DK DK418785A patent/DK418785D0/da not_active Application Discontinuation
  • 1985-09-26 FI FI853708A patent/FI78499C/fi not_active IP Right Cessation

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