EP0480479B2 - Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden - Google Patents

Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden Download PDF

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Publication number
EP0480479B2
EP0480479B2 EP91121100A EP91121100A EP0480479B2 EP 0480479 B2 EP0480479 B2 EP 0480479B2 EP 91121100 A EP91121100 A EP 91121100A EP 91121100 A EP91121100 A EP 91121100A EP 0480479 B2 EP0480479 B2 EP 0480479B2
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Prior art keywords
acid
lubricant
monovalent fatty
chain monovalent
branched
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EP91121100A
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English (en)
French (fr)
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EP0480479A2 (de
EP0480479B1 (de
EP0480479A3 (en
Inventor
Takashi c/o Kyodo Oil Technical Research Kaimai
Hisashi c/o Kyodo Oil Technical Research Yano
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Eneos Corp
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Japan Energy Corp
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    • 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
    • C10N2040/34—Lubricating-sealants
    • 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
    • C10N2040/36—Release agents or mold release agents
    • 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
    • C10N2040/38—Conveyors or chain belts
    • 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
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • 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
    • C10N2040/42—Flashing oils or marking oils
    • 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
    • C10N2040/44—Super vacuum or supercritical use
    • 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
    • C10N2040/50—Medical uses

Definitions

  • This invention relates to the use of lubricants for compressors using a hydrofluorocarbon refrigerant containing no chlorine such as hydrofluorocarbons (HFC), preferably HFC-134a, (1,1,1,2-tetrafluoroethane).
  • HFC hydrofluorocarbons
  • compounds containing fluorine and chlorine as a constituent element such as R-11 (trichloromonofluoromethane), R-12 (dichlorodifluoromethane) as a chlorofluorocarbon (CFC), R-22 (monochlorodifluoromethane) as a hydrochlorofluorocarbon (HCFC) have been used as a refrigerant for freezers, air conditioners and refrigerators, for instance.
  • JP-A-56131548 discloses neopentylpolyolesters useful as freon-resisting oil for lubrication.
  • JP-A-59164393 discloses a refrigerate machine oil which comprises, as base oil, a complex ester synthetized from polyhydric alcohol, 16-18C unsaturated fatty acid and 4-10C dicarboxylic acid.
  • the complex ester has high lubrication and chemical stability and balanced compatibility with freon.
  • freons disclosed in the above references are polyhalogenated hydrocarbons containing fluorine and chlorine.
  • new refrigerants containing no chlorine such as HFC-134a are proposed as a possible replacement for R-12, causing no breakage of ozone layer.
  • Japanese Patent laid open No. 61-281199 describes a mixture of polyglycol represented by a general formula of R 1 [O-(R 2 O) m -R 3 ] n , an alkylbenzene and the like
  • Japanese Patent laid open No. 57-63395 describes an oil obtained by mixing a polyether such as high molecular weight polyoxypropylene monobutyl ether with an epoxycycloalkyl compound
  • Japanese Patent laid open No. 59-117590 describes a high viscosity mixed oil of a polyether compound and a paraffinic or naphthanic mineral oil.
  • the conventional synthetic lubricants as mentioned above cannot be a refrigeration lubricant using HFC-134a as a refrigerant from a viewpoint of compatibility, for instance.
  • polyoxyalkylene glycol (hereinafter abbreviated as PAG) having hydroxyl groups (-OH) at both terminals is reported as a refrigeration lubricant using HFC-134a. Further, it is described that PAG is dissolved in HFC-134a within a wide temperature range as compared with general PAG containing hydroxyl group and alkyl group at its terminals, whereby the recycle of the lubricant into a compressor is improved in the refrigeration system and the seizuring in the actuation of the compressor at high temperature is prevented. Moreover, the temperature range compatible with HFC-134a is described to be between -40°C and +50°C.
  • HFC-134a is a replacing refrigerant of R-12 and is mainly expected for use in a car air conditioner or refrigerator, for instance.
  • the refrigerator it is required to have a good compatibility between lubricant and refrigerant, and further the lubricant itself is necessary to have an electric insulating property because the motor is substantially existent in the refrigeration system.
  • the conventional compounds examined as a lubricant for HFC-134a refrigerant inclusive of PAG disclosed in US Patent No. 4,755,316 are remarkably poor in the electric insulating property as compared with the conventional refrigeration mineral oil and high in the hygroscopicity.
  • esters At the present, a part of commercially available esters is used in systems using refrigerants such as R-12 and R-22, but is incompatible with HFC-134a as a new refrigerant or is very narrow in the compatible range therewith.
  • the inventors have aimed at the fact that the ester has a high electric insulating property, a low hygroscopicity, a good lubricity and a high stability as compared with PAG and made various studies with respect to the molecule design of the ester showing a wide range of compatibility with HFC-134a, and found that only esters having a considerably restricted structure can be used in the HFC-134a refrigeration system, and as a result, the invention has been accomplished.
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, comprising as a main component an ester(s) obtainable by reacting (a) at least one polyvalent alcohol selected from the group consisting of pentaerythritol, dipentaerythritol and tripentaerythritol with (b) a mixture of at least one of straight chain monovalent fatty acids having a carbon number of 3-11 and at least one of branched-chain monovalent fatty acids having a carbon number of 4-14, wherein the amount of the branched-chain monovalent fatty acid is not less than 50 mol% per total monovalent fatty acid used, with the proviso that said lubricant is not used in a liquid composition comprising a major amount (more than 50% by weight) of a fluorine containing hydrocarbon refrigerant and a minor amount of (less than 50% by weight) of said lubricant.
  • the present invention refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine, comprising as a main component an ester(s) obtainable by reacting (a) at least one polyvalent alcohol selected from the group consisting of pentaerythritol, dipentaerythritol and tripentaerythritol with (b) a mixture of at least one of straight chain monovalent fatty acids having a carbon number of 3-11 and at least one of branched-chain monovalent fatty acids having a carbon number of 4-14, wherein the amount of the branched-chain monovalent fatty acid is not less than 50 mol% per total monovalent fatty acid used, and (c) at least one polybasic acid having a carbon number of 4-10, wherein the amount of the polybasic acid is not more than 80 mol% per total fatty acid with the proviso that said lubricant is not used in a liquid composition comprising a major amount (more than
  • the present application also refers to the use of a lubricant for compressors using a hydrofluorocarbon refrigerant containing no chlorine comprising as a main component (an) ester(s) obtainable by reacting (a) at least one polyvalent alcohol selected from pentaerythritol and dipentaerythritol, with (b) at least one branched-chain monovalent fatty acid having a carbon number of 4 to 18, with the proviso that
  • Pentaerythritol, dipentaerythritol and tripentaerythritol are represented by the following formula (I): (in which n is is 1, 2 or 3).
  • the hydrofluorocarbon refrigerant is 1,1,1,2-tetrafluoroethane (HFC-134a).
  • the polymerization degree may be determined in accordance with the viscosity required in the resulting synthesized ester.
  • the monovalent fatty acid mention may be made of propionic acid, butanoic acid, isobutanoic acid, pentanoic acid, isopentanoic acid, hexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, 2-ethyl hexanoic acid, nonanoic acid, 3,5,5-trimethyl hexanoic acid, decanoic acid and undecanoic acid.
  • propionic acid butanoic acid, isobutanoic acid, pentanoic acid, isopentanoic acid, hexanoic acid, heptanoic acid, isoheptanoic acid, octanoic acid, 2-ethyl hexanoic acid, nonanoic acid, 3,5,5-trimethyl hexanoic acid, decanoic acid and undecanoic acid.
  • At least one of branched-chain monovalent fatty acids having a carbon number of 4-18 or a mixture of at least one of straight-chain monovalent fatty acids having a carbon number of 3-11 and at least one of branched-chain monovalent fatty acids having a carbon number of 4-14, is properly mixed and esterified with pentaerythritol or its condensate to obtain an ester satisfying desirable physical properties required for various refrigerators.
  • a mixture of straight chain fatty acid having a carbon number of 3-11, preferably 5-10 and a branched-chain fatty acid having a carbon number of 4-14, preferably 7-9 as the monovalent fatty acid can be used.
  • the amount of the branched-chain fatty acid used is not less than 50 mol% per the total monovalent fatty acid used.
  • At least one polybasic acid having a carbon number of 4-10 may be esterified with at least one of pentaerythritol, dipentaerythritol and tripentaerythritol in an amount of not more than 80 mol% per total fatty acid.
  • the following polybasic acids are used: succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, maleic acid and trimellitic acid.
  • the ester compounds used in the present invention can be obtained by the esterification reaction through dehydration reaction between the specified polyvalent alcohol and the specified fatty acid as mentioned above, or the general esterification reaction through an acid anhydride, an acid chloride or the like as a derivative of the fatty acid.
  • the acid value is preferable to be not more than 3 mg KOH/g and the hydroxyl value is preferable to be not more than 50 mg KOH/g.
  • the esters used in the invention exhibit a good compatibility with the refrigerant HFC-134a and the like over a wide range of from low temperature to high temperature as a lubricant for use in a refrigerator using HFC-134a as a refrigerant, whereby the lubricity and thermal stability of the refrigeration lubricant can be considerably improved. Furthermore, they are high in the electric insulating property and small in the hygroscopicity as compared with PAG conventionally examined as a refrigeration lubricant for HFC-134a.
  • the used refrigeration lubricants comprising the ester used in the invention as a main component the problems on the compatibility with HFC-134a and the hygroscopicity, which have never been solved in the conventional technique, can be solved and the electric insulating property, which comes into problem when HFC-134a is used in a compressor for a refrigerator, can be further enhanced.
  • additives usually used in the lubricant such as antioxidant, anti-wear agent, and epoxy compound, for instance may properly be added to the refrigeration lubricant used in the invention.
  • Seizuring load (Falex load-carrying capacity) was measured according to ASTM D-3233-73 under a controlled atmosphere of HFC-134a blown.
  • test lubricant Into a beaker of 100 ml there were charged 60 g of the test lubricant, which was left to stand at a temperature of 25°C and a humidity of 70% for 3 hours and then the water concentration was measured.
  • esters used in the invention are compared with the commercially available esters (C-1 - C-2) used for comparison shown in Tables 2 and 3, the two-phase separation temperature is extremely different and the conventional esters are insoluble in HFC-134a. In this point, the molecule designed esters used in the invention have a great merit.
  • esters used in the invention are fairly excellent in the performances as a lubricant as compared with those used for comparison.
  • the HFC-134a has been mentioned as a possible replacement for R-12 and is used for car air conditioner and refrigerator, for instance.
  • the compressor is driven in summer season, so that the compatibility between oil and refrigerant at high temperature becomes important.
  • the refrigerant having a larger specific gravity remains in the lower portion of the compressor, resulting in the occurrence of compressor seizuring.
  • the motor is included in the compressor, so that leakage of electricity comes into problem.
  • the esters used in the invention have a dielectric constant higher by 100,000 times or more than that of the conventional PAG and are excellent in the electric insulating property, so that they can be said to be a refrigeration lubricant for the refrigerator.
  • lubricants having a dynamic viscosity of 10-50 mm 2 /s (cSt) at 40°C are used as a lubricant for the refrigerator requiring a two-phase separation temperature of not higher than -40°C, so that the ester A-2 is particularly suitable therefor.
  • lubricants having a dynamic viscosity of 80-150 mm 2 /s (cSt) at 40°C are used as a lubricant for the car air conditioner requiring a two-phase separation temperature of not higher than -20°C, so that the esters A-1, A-3, A-4, and A-6 are particularly suitable therefor.
  • HFC-134a causing substantially no breakage of ozone layer is closed up instead of R-12 widely used as a refrigerant in order to cope with the breakage of ozone layer through chlorofluorocarbon and hydrochlorofluorocarbon being a greatest problem in world-wide scale, but is poor in the compatibility with the conventional refrigeration lubricant, which is a bar for the development of replacement system.
  • the refrigeration lubricants used in the invention have a sufficient compatibility with HFC-134a as a refrigerant and a high electric insulating property and also are excellent in the total performances, so that they have the effect that the conventional systems can be used as they are even when HFC-134a is used instead of the conventional R-12 and R-22 as a refrigerant.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (16)

  1. Verwendung eines Schmiermittels für Kompressoren unter Verwendung eines Fluorkohlenwasserstoff-Kühlmittels, das kein Chlor enthält, umfassend als Hauptbestandteil (einen) Ester, erhältlich durch Umsetzen von (a) mindestens einem polyvalenten Alkohol, ausgewählt aus Pentaerythritol, Dipentaerythritol und Tripentaerythritol mit (b) einer Mischung von mindestens einer von geradkettigen monovalenten Fettsäuren mit einer Kohlenstoffanzahl von 3 - 11 mit mindestens einer von verzweigtkettigen monovalenten Fettsäure mit einer Kohlenstoffanzahl von 4 - 14, worin die Menge der verzweigtkettigen monovalenten Fettsäure nicht weniger als 50 mol-% pro verwendete Gesamtmenge monovalenter Fettsäure ist, mit der Massgabe, dass das Schmiermittel nicht in einer flüssigen Zusammensetzung, die als Hauptbestandteil (mehr als 50 Gew.-%) ein fluorhaltiges Kohlenwasserstoff-Kühlmittel und als Nebenbestandteil (weniger als 50 Gew.-%) das Schmiermittel enthält, verwendet wird.
  2. Verwendung eines Schmiermittels nach Anspruch 1, worin die geradkettige monovalente Fettsäure ausgewählt ist aus Propansäure; Butansäure, Pentansäure, Hexansäure, Heptansäure, Octansäure, Nonansäure, Decansäure und Undecansäure, und die verzweigtkettige monovalente Fettsäure ausgewählt ist aus Isobutansäure, Isopentansäure, Isoheptansäure, 2-Ethylhexansäure und 3,5,5-Trimethylhexansäure.
  3. Verwendung eines Schmiermittels nach Anspruch 1, worin die verzweigtkettige monovalente Fettsäure eine mit einer Kohlenstoffanzahl von 7 - 9 ist.
  4. Verwendung eines Schmiermittels nach einem der Ansprüche 1 bis 3, worin der Ester eine Gesamtsäurezahl von nicht mehr als 3 mgKOH/g und eine Hydroxylzahl von nicht mehr als 50 mgKOH/g hat.
  5. Verwendung eines Schmiermittels nach einem der Ansprüche 1 bis 4, worin das Fluorkohlenwasserstoff-Kühlmittel 1,1,1,2-Tetrafluorethan ist.
  6. Verwendung eines Schmiermittels für Kompressoren unter Verwendung eines Fluorkohlenwasserstoff-Kühlmittels, das kein Chlor enthält, umfassend als Hauptbestandteil (einen) Ester, erhältlich durch Umsetzen von (a) mindestens einem polyvalenten Alkohol, ausgewählt aus Pentaerythritol, Dipentaerythritol und Tripentaerythritol mit (b) einer Mischung von mindestens einer von geradkettigen monovalenten Fettsäuren mit einer Kohlenstoffanzahl von 3 - 11 mit mindestens einer von verzweigtkettigen monovalenten Fettsäure mit einer Kohlenstoffanzahl von 4 - 14, worin die Menge der verzweigtkettigen monovalenten Fettsäure nicht kleiner ist als 50 mol-% pro verwendeter Gesamtmenge an monovalenter Fettsäure, und (c) mindestens einer polybasischen Säure mit einer Kohlenstoffanzahl von 4 - 10, worin die Menge der polybasischen Säure nicht mehr als 80 mol-% pro Gesamtfettsäure ist, mit der Massgabe, dass das Schmiermittel nicht in einer flüssigen Zusammensetzung, die als Hauptbestandteil (mehr als 50 Gew.-%) ein fluorhaltiges Kohlenwasserstoff-Kühlmittel und als Nebenbestandteil (weniger als 50 Gew.-%) das Schmiermittel enthält, verwendet wird.
  7. Verwendung eines Schmiermittels nach Anspruch 6, worin die geradkettige monovalente Fettsäure ausgewählt ist aus Propionsäure, Butansäure, Pentansäure, Hexansäure, Heptansäure, Octansäure, Nonansäure, Decansäure und Undecansäure, und die verzweigtkettige monovalente Fettsäure ausgewählt ist aus Isobutansäure, Isopentansäure, Isoheptansäure, 2-Ethylhexansäure und 3,5,5-Trimethylhexansäure.
  8. Verwendung eines Schmiermittels nach Anspruch 6, worin die polybasische Säure ausgewählt ist aus Succinsäure, Glutarsäure, Adipinsäure, Pimelinsäure, Suberinsäure, Azelainsäure und Sebacinsäure.
  9. Verwendung eines Schmiermittels nach einem der Ansprüche 6 bis 8, worin der Ester eine Gesamtsäurezahl von nicht mehr als 3 mgKOH/g und eine Hydroxylzahl von nicht mehr als 50 mgKOH/g hat.
  10. Verwendung eines Schmiermittels nach einem der Ansprüche 6 bis 9, worin das Fluorkohlenwasserstoff-Kühlmittel 1,1,1,2-Tetrafluorethan ist.
  11. Verwendung eines Schmiermittels für Kompressoren unter Verwendung eines Fluorkohlenwasserstoff-Kühlmittels, das kein Chlor enthält, das als Hauptkomponente (einen) Ester umfasst, erhältlich durch Umsetzen von (a) mindestens einem polyvalenten Alkohol, ausgewählt aus Pentaerythritol und Dipentaerythritol mit (b) mindestens einer verzweigtkettigen monovalenten Fettsäure mit einer Kohlenstoffanzahl von 4 bis 18, mit der Massgabe, dass
    (i) das Schmiermittel kein Polyetherpolyol in einer Menge 5 bis 95 Gew.-% gemäss der allgemeinen Formel Z-[(CH2CH(R1)-O-)n-(CH2-CH(CH3)-O-)m-R2]p    enthält, worin
       Z der Rest einer Verbindung mit 1 bis 8 aktiven Wasserstoffen ist,
       R ist Wasserstoff, Ethyl oder Mischungen davon
       n ist 0 oder eine positive Zahl,
       m ist eine positive Zahl,
       n+m ist eine Zahl mit einem Wert, welcher dem Polyetherpolyol eine mittlere
       Molekulargewichtszahl im Bereich von ca. 400 bis ca. 5000 verleiht,
       R2 ist Wasserstoff oder eine Alkylgruppe mit 1 bis 6 Kohlenstoffatomen,
       p ist eine ganze Zahl mit einem Wert,
       entsprechend der Zahl der aktiven Wasserstoffe von Z,
       und
    (ii) das Schmiermittel nicht in einer flüssigen Zusammensetzung, die als Hauptbestandteil (mehr als 50 Gew.-%) ein fluorhaltiges Kohlenwasserstoff-Kühlmittel und als Nebenbestandteil (weniger als 50 Gew.-%) das Schmiermittel enthält, verwendet wird.
  12. Verwendung eines Schmiermittels nach Anspruch 11, worin der polyvalente Alkohol Pentaerythritol ist.
  13. Verwendung eines Schmiermittels nach Anspruch 11 oder 12, worin die verzweigtkettige monovalente Fettsäure ausgewählt ist aus Isobutansäure, Isopentansäure, Isoheptansäure, 2-Ethylhexansäure und 3,5,5-Trimethylhexansäure.
  14. Verwendung eines Schmiermittels nach Anspruch 11 oder 12, worin die verzweigtkettige monovalente Fettsäure eine mit einer Kohlenstoffanzahl von 7 - 9 ist.
  15. Verwendung eines Schmiermittels nach Anspruch 14, worin die verzweigtkettige monovalente Fettsäure ausgewählt ist aus Isoheptansäure, 2-Ethylhexansäure und 3,5,5-Trimethylhexansäure.
  16. Verwendung eines Schmiermittels nach einem der Ansprüche 11 bis 15, worin das Fluorkohlenwasserstoff-Kühlmittel 1,1,1,2-Tetrafluorethan ist.
EP91121100A 1989-07-05 1989-10-17 Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden Expired - Lifetime EP0480479B2 (de)

Applications Claiming Priority (10)

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JP17200289 1989-07-05
JP172000/89 1989-07-05
JP172001/89 1989-07-05
JP17200189 1989-07-05
JP17200089 1989-07-05
JP17200189 1989-07-05
JP172002/89 1989-07-05
JP17200089 1989-07-05
JP17200289 1989-07-05
EP89119265A EP0406479B2 (de) 1989-07-05 1989-10-17 Kältemaschinenschmiermittel

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EP89119265A Division EP0406479B2 (de) 1989-07-05 1989-10-17 Kältemaschinenschmiermittel
EP89119265A Division-Into EP0406479B2 (de) 1989-07-05 1989-10-17 Kältemaschinenschmiermittel

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EP0480479A2 EP0480479A2 (de) 1992-04-15
EP0480479A3 EP0480479A3 (en) 1992-06-17
EP0480479B1 EP0480479B1 (de) 1997-03-26
EP0480479B2 true EP0480479B2 (de) 2004-09-01

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EP91121101A Expired - Lifetime EP0479338B1 (de) 1989-07-05 1989-10-17 Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden.
EP91121100A Expired - Lifetime EP0480479B2 (de) 1989-07-05 1989-10-17 Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden
EP89119265A Expired - Lifetime EP0406479B2 (de) 1989-07-05 1989-10-17 Kältemaschinenschmiermittel
EP92121965A Expired - Lifetime EP0536814B1 (de) 1989-07-05 1989-10-17 Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden.

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EP0480479A2 (de) 1992-04-15
ES2104650T3 (es) 1997-10-16
DE68925537D1 (de) 1996-03-07
ES2099120T5 (es) 2005-03-16
EP0480479B1 (de) 1997-03-26
DE68925537T2 (de) 1996-07-04
EP0406479A1 (de) 1991-01-09
DE68927916T3 (de) 2005-03-10
ES2082341T3 (es) 1996-03-16
ES2099120T3 (es) 1997-05-16
EP0480479A3 (en) 1992-06-17
EP0406479B1 (de) 1994-04-06
DE68914448T3 (de) 2003-03-06
KR970078831A (ko) 1997-12-12
DE68914448T2 (de) 1994-08-25
EP0536814A1 (de) 1993-04-14
DE68914448D1 (de) 1994-05-11
DE68928281D1 (de) 1997-10-02
ES2051340T3 (es) 1994-06-16
EP0479338A3 (en) 1992-05-27
SG49157A1 (en) 1998-05-18
KR0131016B1 (ko) 1998-04-14
SG49165A1 (en) 1998-05-18
EP0406479B2 (de) 2002-09-04
ES2051340T5 (es) 2003-03-16
KR910003077A (ko) 1991-02-26
KR950005694B1 (ko) 1995-05-29
DE68927916D1 (de) 1997-04-30
KR970078832A (ko) 1997-12-12
KR0131017B1 (ko) 1998-04-14
EP0479338A2 (de) 1992-04-08
DE68928281T2 (de) 1998-01-15
DE68927916T2 (de) 1997-08-21
EP0479338B1 (de) 1997-08-27
EP0536814B1 (de) 1996-01-24

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