EP0452509A1 - Utilisation d'huile lubrifiante synthetique a base de polyester comme lubrifiante pour un refrigerateur - Google Patents

Utilisation d'huile lubrifiante synthetique a base de polyester comme lubrifiante pour un refrigerateur Download PDF

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Publication number
EP0452509A1
EP0452509A1 EP90916360A EP90916360A EP0452509A1 EP 0452509 A1 EP0452509 A1 EP 0452509A1 EP 90916360 A EP90916360 A EP 90916360A EP 90916360 A EP90916360 A EP 90916360A EP 0452509 A1 EP0452509 A1 EP 0452509A1
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EP
European Patent Office
Prior art keywords
lubricating oil
group
compression
carbon atoms
refrigerant
Prior art date
Legal status (The legal status 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 status listed.)
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Application number
EP90916360A
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German (de)
English (en)
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EP0452509B1 (fr
EP0452509B9 (fr
EP0452509A4 (en
Inventor
Hideo Idemitsu Kosan Co. Ltd. Ohhama
Nobuaki Idemitsu Kosan Co. Ltd. Shimizu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Idemitsu Kosan Co Ltd
Original Assignee
Idemitsu Kosan Co Ltd
Idemitsu Petrochemical Co Ltd
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Publication of EP0452509A1 publication Critical patent/EP0452509A1/fr
Publication of EP0452509A4 publication Critical patent/EP0452509A4/en
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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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • 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
    • 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
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/008—Lubricant compositions compatible with refrigerants
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C—CHEMISTRY; METALLURGY
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/061—Carbides; Hydrides; Nitrides
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/16—Carbon dioxide
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    • C10M2201/18—Ammonia
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2040/32—Wires, ropes or cables lubricants
    • 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
    • C10N2040/34—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

  • the present invention relates to a polyester synthetic lubricating oil and more particularly to a polyester synthetic lubricating oil suitable as a lubricating oil for a variety of use, especially as a lubricating oil for refrigerating machine. Still more particularly, it pertains to a polyester synthetic lubricating oil which has favorable miscibility with hydrogen-containing fluorocarbons (hydrogen-containing fluoroalkanes) (hereinafter referred to as "hydrogenated Flon compounds”) such as 1,1,1,2-tetrafluoroethane (hereinafter referred to as "Flon 134a”) capable of being used as replacements of fluorocarbons (Flon compounds) such as dichlorodifluoromethane (hereinafter referred to as "Flon 12”) as refrigerants now causing a serious environmental pollution problem, and at the same time, is excellent in lubrication performance and particularly suitable as a lubricating oil for a compression-type refrigerating machine.
  • a lubricating oil especially that for a refrigerator (refrigerating machine) is required to have favorable miscibility with an refrigerant used in a refrigerator.
  • an refrigerant for a compression-type refrigerator Flon 12 or the like has heretofore been used.
  • Flon 12 has recently been revealed as one of the causes of environmental pollution. As such, particular attention is being paid to hydrogenated Flon compounds such as Flon 134a as replacements.
  • lubricating oils having favorable miscibility with the above Flon 134a for example, Ulcon LB-165 and LB-525 (trade name, both produced by Union Carbide Co., Ltd.) composed of polyalkyleneglycol has been known, and it was reported that these lublicating oils are miscible with Flon 134a over the entire proportions at a low temperature of at least -50°C ("Research Disclosure", No. 17463 (October, 1978)).
  • high viscosity refrigerator oil compositions employing polyoxypropylene glycol monobutyl ether as a base oil been known (Japanese Patent Publication No. 42119/1982).
  • these lubricating oils are poly(alkylene glycol) derivatives having polypropylene glycol with hydroxyl group at one terminal and an n-butyl ether bond at the other terminal. They have comparatively good miscibility with Flon 134a at lower temperature, but do not have sufficient miscibility with Flon 134a at higher temperature, and for example, Ulcon LB-525 as descirbed above is known to cause phase separation from Flon 134a at room temperature (Specification of US Pat. No. 4755316).
  • polyglycol having at least two hydroxyl groups in a molecule is proposed as a substance having favorable miscibility with Flon 134a (Specification of US Pat. No. 4755316).
  • the above disclosed polyglycol has not necessarily sufficient miscibility with Flon 134a.
  • the present invention as disclosed hereunder has been accomplished in response to the above desire for the purpose of providing a novel lubricating oil for compression-type reprigerators having excellent lubrication performance as well as favorable miscibility over the entire working temperature range with hydrogenated Flon compounds such as Flon 134a which can be substituted for refrigerant such as Flon 12 or other Flon compounds difficult to decompose, causing environmental pollution problems and at the same time, of providing a lubricating oil capable of developing another use.
  • hydrogenated Flon compounds such as Flon 134a which can be substituted for refrigerant such as Flon 12 or other Flon compounds difficult to decompose, causing environmental pollution problems and at the same time, of providing a lubricating oil capable of developing another use.
  • a lubricating oil comprising as an essential component an aliphatic polyester derivative having a specific structure can meet the above purpose.
  • the present invention has been accomplished on the basis of such a finding.
  • polyester synthetic lubricating oil which comprises, as an essential component, an aliphatic polyester derivative having a molecular weight in the range of 300 to 2000 and having at least one constitutional unit represented by the general formula (I) wherein R1 is an alkylene group having 1 to 10 carbon atoms, and R2 is an alkylene group having 2 to 10 carbon atoms or an oxaalkylene group having 4 to 20 carbon atoms.
  • the present invention provides as the second aspect thereof a method for lubrication characterized by lubricating a compression-type refrigerator wherein hydrogenated Flon compounds are used as a refrigerant by the use of the above-mentioned polyester synthetic lubricating oil. Still furthermore, the present invention provides as the third aspect thereof a compression-type refrigeration system comprising a compressor, a refrigerant of hydrogenated Flon compounds, and the above polyester synthetic lubricating oil.
  • the lubricating oil according to the present invention comprises, as an essential component, an aliphatic polyester derivative having at least one constitutional unit (repeating unit) represented by the general formula (I).
  • R1 stands for an alkylene group having 1 to 10 carbon atoms.
  • R2 designates an alkylene group having 2 to 10 carbon atoms or an oxaalkylene group having 4 to 20 carbon atoms.
  • alkylene group are same as those of the above-mentioned R1 excluding methylene group, and preferably an alkylene group having 2 to 6 carbon atoms.
  • oxaalkylene group include 3-oxa-1,5-pentylene group; 3,6-dioxa-1,8-octylene group; 3,6,9-trioxa-1,1,1-undecylene group; 3-oxa-1,4-dimethyl-1,5-pentylene group; 3,6-dioxa-1,4,7-trimethyl-1,8-octylene group; 3,6,9-trioxa-1,4,7,10-tetramethyl-1,11-undecylene group; 3-oxa-1,4-diethyl-1,5-pentylene group; 3,6-dioxa-1,4,7-triethyl-1,8-octylene group; 3,6,9-trioxa-1,4,7,10-t
  • the aliphatic polyester derivative represented by the general formula (I) it is necessary for the aliphatic polyester derivative represented by the general formula (I) to have a molecular weight in the range of 300 to 2000 as measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • the aliphatic polyester derivative as described above represented by the general formula (I) can be prepared by a variety of methods, for example, by the publicly known process for preparing polyester. Specific examples include (i) direct esterification process and (ii) ester exchange process as detailed hereunder.
  • the direct esterification processs is the process wherein a dihydric alcohol and a dibasic carboxylic acid are subjected to dehydration-condensation without any catalyst or in the presence of an acid catalyst.
  • the reaction temperature during the process is usually in the range of 50 to 400°C, preferably 70 to 250°C and particularly preferably 100 to 180°C. If the reaction temperature is too high, decomposition or solidification takes place. On the other hand, if it is too low, the reaction hardly proceeds.
  • the reaction time is usually in the range of one minute to 20 hours, preferably 10 minutes to 10 hours.
  • the reaction may be carried out at ordinary pressure or a reduced pressure. Alternatively, two-stage reaction may be effected including half-ester synthesis at ordinary pressure followed by synthesis completion at a reduced pressure.
  • esterification catalysts As the esterification catalysts, a cation-exchange resin, sulfuric acid, hydrochloric acid, p-toluene sulfonic acid, methanesulfonic acid, activated clay, zeolites of various types, silicotungstic acid, phosphotungstic acid, etc. may be usually used.
  • the proportion in terms of molar ratio of a dihydric alcohol to a dibasic carboxylic acid each as raw material is usually in the range of 0.5 to 2.0, preferably 0.8 to 1.5 and particularly preferably 0.9 to 1.2.
  • the reaction process may be either batchwise or continuous.
  • the ester exchange process is the process wherein a dihydric alcohol and a diester of a dibasic carboxylic acid is subjected to condensation in the absence or presence of a catalyst.
  • the reaction temperature during the process is usually in the range of 50 to 400°C, preferably 70 to 250°C and particularly preferably 100 to 180°C. If the temperature is too high, decomposition or solidification due to difficulty in polymerization control will occur. On the contrary, if it is too low, reaction rate is lowered.
  • the reaction time is ordinarily in the range of one minute to 20 hours, preferably 10 minutes to 10 hours.
  • the reaction may be carried out at ordinary pressure or a reduced pressure. Alternatively, two-stage reaction may be performed including half-ester synthesis at ordinary pressure followed by synthesis completion at a reduced pressure.
  • an acid or base catalyst may be optionally selected.
  • a diester as raw material can be exemplified by a diester prepared by dehydration-condensation of a dibasic carboxylic acid and an arbitrary monohydric alcohol in addition to the above-mentioned dibasic carboxylic acid.
  • the proportion in terms of molar ratio of a dihydric alcohol to a dibasic carboxylic acid each as raw material is usually in the range of 0.5 to 2.0, preferably 0.8 to 1.5 and particularly preferably 0.9 to 1.2.
  • the reaction process may be either batchwise or continuous.
  • dibasic carboxylic acid to be used as raw material in the aforementioned (i) direct esterification process or (ii) Ester exchange process include, for instance, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, etc.
  • diesters of dibasic carboxylic acid include dimethyl ester, diethyl ester each of the above dibasic carboxylic acid.
  • the above-mentioned process may be applied to the preparation of the aliphatic polyester derivatives to be used in the present invention.
  • modification may be made to improve miscibility, viscosity index and lubricity and to reduce hygroscopicity by allowing terminal hydroxyl groups in whole or in part to lead to the formation of ester or ether.
  • the hydrocarbon groups in the residual groups of the ester or ether have preferably 1 to 10 carbon atoms.
  • carboxylic acids are formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, capric acid, caprylic acid, cyclohexanecarboxylic acid, etc.
  • esterification by the use of the above-mentioned carboxylic acid or acid anhydride thereof or esterification by ester exchange by the use of the carboxylic acid ester an acid catalyst such as sulfuric acid, p-toluene sulfonic acid, etc. is ordinarily used.
  • an acid catalyst such as sulfuric acid, p-toluene sulfonic acid, etc. is ordinarily used.
  • an acid halide an amine is generally used as a hydrogen halide removing agent.
  • the esterification may be carried out during or after the preparation of an aliphatic polyester.
  • a dialkyl sulfate having 1 to 10 carbon atoms, an alkyl halide or a sulfonic acid ester each having 1 to 10 carbon atoms is allowed to react with the above polyester derivative, or another process wherein the hydroxyl group in the aliphatic polyester derivatives is converted into a sulfonic acid ester or a halide, which thereafter is subjected to reaction with an aliphatic alcohol of 1 to 10 carbon atoms or alkali metal salt thereof.
  • the kinematic viscosity of the lubricating oil before blending with a refrigerant is preferably in the range of 10 to 1000 cSt.
  • starting materials, other additives and reaction conditions for the aliphatic polyester derivative be selected so as to provide the lubricating oil with a kinematic viscosity within the aforementioned range.
  • lubricating oil In the lubricating oil according to the present invention, single compound or a mixture of at least two compounds from among the aliphatic polyester derivatives represented by the general formula (I) is employed, and as the case may be, together with other kind of lubricating oil.
  • various additives that are used in the conventional lubricating oils such as load resistant additives (extreme pressure agent, oiliness agent, anti-wear additive, etc.), chlorine capturing agent, antioxidants, metal deactivators, defoaming agents, detergent-dispersants, viscosity-index improvers, antirust agents, corrosion inhibitors, pour point depressants, etc. may be optionally blended according to demand or desire.
  • organic sulfide additives such as monosulfides, polysulfides, sulfoxides, sulfones, thiosulfinates, sulfurized oil and fat, thiocarbonates, thiophenes, thiazoles, methanesulfonic acid esters, etc.
  • phosphate additives such as phosphoric monoesters, phosphoric diesters, phosphoric triesters (tricresyl phosphate) etc.
  • phosphite additives such as phosphorus monoesters, phosphorus diesters, phosphorus triesters, etc.
  • thiophosphate additives such as thiophosphoric acid triesters
  • fatty acid additives such as higher fatty acids, hydroxyaryl fatty acids, carboxylic acid-containing polyhydric alcohol esters, metallic soap, etc.
  • fatty acid ester additives such as polyhydric alcohol esters, acrylic esters, etc.
  • organic chlorine additives such as chloride
  • chlorine capturing agents there can be mentioned compounds having glycidyl ether group, epoxy fatty acid monoesters, epoxidized fats and oils, compounds having epoxy cycloalkyl group, etc.
  • antioxidants there can be included phenols (2.6-di-tert-butyl-p-cresol), aromatic amines ( ⁇ -naphthylamine), etc.
  • metal deactivators there can be mentioned benzotriazole derivatives, etc.
  • silicone oil dimethylpolysiloxane
  • polymethacrylates, etc. can be included.
  • detergent dispersants sulfonates, phenates, succinimides, etc. can be included.
  • viscosity index improvers polymethacrylates, polyisobutylene, ethylene-propylene copolymer, hydrogenated styrene-diene copolymer, etc. can be exemplified.
  • a prescribed amount of a sample and Flon 134a were placed in a pressure glass ampule so that the sample would be 10% and 20% by weight, respectively to Flon 134a.
  • the ampule was connected to a vacuum line and Flon 134a-gas line, subjected to vacuum degassing at room temperature and thereafter cooled with liquid nitrogen to take out the prescribed amount of Flon 134a containing the sample.
  • the lubricating oil according to the present invention can be used for a variety of applications and is suitable for the lubrication of a refrigerator, especially of a compression-type refrigerator.
  • the lubricating oil according to the present invention has satisfactory miscibility with hydrogenated Flon compounds such as Flon 134a (most popular), 1,1-dichloro-2,2,2-trifluoroethane (Flon 123), 1-chloro-1,1-difluoroethane (Flon 142b), 1-1-difluoroethane (Flon 152a), chlorodifluoromethane (Flon 22), trifluoromethane (Flon 23), etc.
  • Flon 134a most popular
  • 1,1-dichloro-2,2,2-trifluoroethane Flon 123
  • 1-chloro-1,1-difluoroethane Flon 142b
  • 1-1-difluoroethane Flon 152a
  • chlorodifluoromethane Flon 22
  • trifluoromethane Flon 23
  • the lubricating oil according to the present invention is particularly well suited for a compression-type refrigerator in which a hydrogenated Flon compound, especially Flon 134a is used as a refrigerant.

Landscapes

  • 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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Huile lubrifiante synthétique à base d'un dérivé de polyester aliphatique comportant des unités répétitives représentées par la formule générale (I), dans laquelle R1 et R2 correspondent à la spécification, et un poids moléculaire compris entre 300 et 2000. Cette huile lubrifiante présente d'excellentes caractéristiques de lubrification et de compatibilité avec un réfrigérant, ce qui permet de l'utiliser dans un réfrigérateur, notamment un réfrigérateur à compression.
EP90916360A 1989-11-13 1990-11-13 Utilisation d'huile lubrifiante synthetique a base de polyester comme lubrifiante pour un refrigerateur Expired - Lifetime EP0452509B9 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP292283/89 1989-11-13
JP29228389 1989-11-13
JP29228389 1989-11-13
PCT/JP1990/001468 WO1991007479A1 (fr) 1989-11-13 1990-11-13 Huile lubrifiante synthetique a base de polyester

Publications (4)

Publication Number Publication Date
EP0452509A1 true EP0452509A1 (fr) 1991-10-23
EP0452509A4 EP0452509A4 (en) 1992-04-01
EP0452509B1 EP0452509B1 (fr) 1994-07-06
EP0452509B9 EP0452509B9 (fr) 2002-05-08

Family

ID=17779748

Family Applications (1)

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EP90916360A Expired - Lifetime EP0452509B9 (fr) 1989-11-13 1990-11-13 Utilisation d'huile lubrifiante synthetique a base de polyester comme lubrifiante pour un refrigerateur

Country Status (4)

Country Link
EP (1) EP0452509B9 (fr)
DE (1) DE69010486T2 (fr)
ES (1) ES2060204T3 (fr)
WO (1) WO1991007479A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0501440A1 (fr) * 1991-02-26 1992-09-02 Kao Corporation Composition utilisée comme fluide de travail pour machine frigorifique
WO1993014176A1 (fr) * 1992-01-10 1993-07-22 Ethyl Corporation Compositions refrigerantes
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
EP0979859A1 (fr) * 1998-08-05 2000-02-16 FUCHS DEA Schmierstoffe GmbH & Co. KG Compositions de fluides de travail comprenant du dioxide de carbon et un polyester
US6582621B1 (en) 1989-12-28 2003-06-24 Nippon Mitsubishi Oil Corporation Refrigerator oils for use with chlorine-free fluorocarbon refrigerants
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5374366A (en) * 1992-04-15 1994-12-20 Sanken Chemical Co., Ltd. Synthetic lubricating oil
EP1681341B1 (fr) 1999-03-05 2010-06-02 Idemitsu Kosan Co., Ltd. Composition huileuse pour machines refrigérantes
JP4156892B2 (ja) * 2002-09-24 2008-09-24 新日本石油株式会社 冷凍機油

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2926139A (en) * 1952-11-08 1960-02-23 Bayer Ag Lubricants for refrigerating systems
GB1460665A (en) * 1974-02-11 1977-01-06 Ciba Geigy Ag Transmission device
JPS5821957B2 (ja) * 1978-04-01 1983-05-04 川崎製鉄株式会社 表面処理鋼板の防護用表面油
JPS60133022A (ja) * 1983-12-20 1985-07-16 Osaka Suiso Kogyo Kk 重縮合物
GB8806923D0 (en) * 1988-03-23 1988-04-27 Ici Plc Lubricants
JPH0662977B2 (ja) * 1988-04-08 1994-08-17 株式会社共石製品技術研究所 フロン圧縮機用冷凍機油
JP2556548B2 (ja) * 1988-04-08 1996-11-20 株式会社ジャパンエナジー フロン圧縮機に用いる潤滑油
JP2556547B2 (ja) * 1988-04-08 1996-11-20 株式会社ジャパンエナジー カーエアコン用フロン圧縮機用潤滑油
JP2801703B2 (ja) * 1989-09-01 1998-09-21 花王株式会社 冷凍機油
DK0435253T3 (da) * 1989-12-28 1994-06-20 Nippon Oil Co Ltd Køleolier til brug sammen med hydrogenholdige halogencarbonkølemidler

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6582621B1 (en) 1989-12-28 2003-06-24 Nippon Mitsubishi Oil Corporation Refrigerator oils for use with chlorine-free fluorocarbon refrigerants
EP0501440A1 (fr) * 1991-02-26 1992-09-02 Kao Corporation Composition utilisée comme fluide de travail pour machine frigorifique
WO1993014176A1 (fr) * 1992-01-10 1993-07-22 Ethyl Corporation Compositions refrigerantes
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
EP0979859A1 (fr) * 1998-08-05 2000-02-16 FUCHS DEA Schmierstoffe GmbH & Co. KG Compositions de fluides de travail comprenant du dioxide de carbon et un polyester
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems

Also Published As

Publication number Publication date
ES2060204T3 (es) 1994-11-16
DE69010486T2 (de) 1994-10-27
WO1991007479A1 (fr) 1991-05-30
EP0452509B1 (fr) 1994-07-06
EP0452509B9 (fr) 2002-05-08
DE69010486D1 (de) 1994-08-11
EP0452509A4 (en) 1992-04-01

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