EP0406479A1 - Kältemaschinenschmiermittel - Google Patents

Kältemaschinenschmiermittel Download PDF

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Publication number
EP0406479A1
EP0406479A1 EP89119265A EP89119265A EP0406479A1 EP 0406479 A1 EP0406479 A1 EP 0406479A1 EP 89119265 A EP89119265 A EP 89119265A EP 89119265 A EP89119265 A EP 89119265A EP 0406479 A1 EP0406479 A1 EP 0406479A1
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EP
European Patent Office
Prior art keywords
acid
carbon number
hfc
lubricant
none
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.)
Granted
Application number
EP89119265A
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English (en)
French (fr)
Other versions
EP0406479B1 (de
EP0406479B2 (de
Inventor
Takashi C/O Kyodo Oil Technical Research Kaimai
Hisashi C/O Kyodo Oil Technical Research Yano
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.)
Eneos Corp
Original Assignee
KYOSEKI SEIHIN GIJUTSU KENK
Kyodo Oil Technical Research Center Co Ltd
Japan Energy Corp
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=27323564&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0406479(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by KYOSEKI SEIHIN GIJUTSU KENK, Kyodo Oil Technical Research Center Co Ltd, Japan Energy Corp filed Critical KYOSEKI SEIHIN GIJUTSU KENK
Priority to EP91121100A priority Critical patent/EP0480479B2/de
Priority to EP92121965A priority patent/EP0536814B1/de
Priority to EP91121101A priority patent/EP0479338B1/de
Publication of EP0406479A1 publication Critical patent/EP0406479A1/de
Publication of EP0406479B1 publication Critical patent/EP0406479B1/de
Application granted granted Critical
Publication of EP0406479B2 publication Critical patent/EP0406479B2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/34—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 lubricants used with refrigerants, and more particularly to lubricants suitable for use in the compression of refrigerants containing no chlorine such as hydroflorocarbons (HFC), preferably HFC-134a (1,1,1,2-tetrafluoroethane) and the like.
  • HFC hydroflorocarbons
  • HFC-134a 1,1,1,2-tetrafluoroethane
  • Japanese Patent laid open No. 61-281199 describes a mixture of polyglycol represented by a general formula of R1[O-(R2O) m -R3] n , an alkylbenzene and !6 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 can not be a refrigeration lubricant using HFC-134a as a refrigerant from a viewpoint of compatibility and the like.
  • 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, a refrigerator and the like.
  • 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.
  • an object of the invention to provide a refrigeration lubricant having an excellent compatibility with a new refrigerant such as HFC-134a or the like within a wide temperature range, a high electric insulating property and a low hygroscopicity.
  • esters At the present, a part of commercially available esters is used in systems using refrigerants R-12, R-22 and the like, 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.
  • a lubricant for hydrofluoro­carbon refrigerant such as HFC-134a and the like comprising as a main component an ester comprised of neopentyl glycol and at least one straight or branched-­chain monovalent fatty acid having a carbon number of 3-18.
  • a lubricant for hydrofluoro­carbon refrigerant such as HFC-134a and the like comprising as a main component an ester comprised of at least one of pentaerythritol, dipentaerythritol and tripentaerythritol represented by the following general formula (I): (in which n is 1, 2 or 3), and at least one straight or branched-chain monovalent fatty acid having a carbon number of 2-18.
  • a lubricant for hydrofluoro­carbon refrigerant such as HFC-134a and the like comprising as a main component an ester comprised of a polyvalent alcohol represented by the following general formula (II): (in which R is an alkyl group having a carbon number of not more than 3), at least one straight or branched-­chain monovalent fatty acid having a carbon number of 2-18, and not more than 25 mol% per total fatty acid of at least one polybasic acid having a carbon number of 4-36.
  • R is an alkyl group having a carbon number of not more than 3
  • the hydrofluorocarbon refrigerant is 1,1,1,2-­tetrafluoroethane (HFC-134a).
  • the refrigeration lubricant for refrigerant HFC-134a and the like according to the first invention comprises an ester obtained by esterifying neopentyl glycol with at least one straight or branched-chain monovalent fatty acid having a carbon number of 3-18 as a main component.
  • the reason why the carbon number of the monovalent fatty acid is limited to 3-18 is due to the fact that when the carbon number is less than 3, the viscosity is too low, while when it exceeds 18, the resulting ester becomes cloudy or becomes very poor in the compatibility with the refrigerant HFC-134a and the like.
  • the monovalent fatty acid mention may be made of propionic acid, isopropionic 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, undecanoic acid, lauric acid, myristic acid, palmitic acid, palmitooleic acid, stearic acid, isostearic acid, oleic acid, and the like.
  • At least one of these monovalent fatty acids is properly mixed and esterified with neopentyl glycol to obtain an ester satisfying desirable physical properties required for various refrigerators.
  • the amount of the straight or branched-chain fatty acid used is preferable to be not less than 50 mol% per the total monovalent fatty acid used.
  • At least one polybasic acid having a carbon number of 4-36 may be esterified with neopentyl glycol in an amount of not more than 80 mol% per total fatty acid.
  • the polybasic acids considering the more compatibility with the refrigerant HFC-134a and the like and the physical properties of the resulting ester, a polybasic acid having a carbon number of 4-10 is preferable.
  • the polybasic acid includes succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, maleic acid, trimellitic acid and so on.
  • the polybasic acid having a carbon number of not more than 3 is a special product and is difficult to be cheaply available and is poor in the stability of the ester after the synthesis. While, when the carbon number exceeds 36, the compatibility of the resulting ester with HFC-134a and the like is largely lowered.
  • the reason why the amount of the polybasic acid added is limited to not more than 80 mol% per the total fatty acid is due to the fact that when it exceeds 80 mol%, the gelation may be caused and it is difficult to obtain desirable physical properties.
  • the ester compounds according to the first 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 ester according to the invention can be obtained by the above method, the remaining acid value and hydroxyl value are not particularly critical.
  • the acid value exceeds 3
  • the acid value exceeds 50
  • the hydroxyl value exceeds 50
  • the hydroxyl value exceeds 50
  • the lubricant for refrigerant HFC-134a and the like according to the second invention comprises an ester obtained by esterifying at least one of pentaerythritol, dipentaerythritol and tripenta­erythritol represented by the aforementioned general formula (I) with at least one straight or branched-chain monovalent fatty acid having a carbon number of 2-18 as a main component.
  • the polymerization degree may be determined in accordance with the viscosity required in the resulting synthesized ester.
  • the carbon number of the monovalent fatty acid is limited to 2-18 because when it exceeds 18, the resulting ester becomes cloudy or becomes very poor in the compatibility with the refrigerant HFC-134a and the like.
  • the monovalent fatty acid mention may be made of acetic acid, propionic acid, isopropionic 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, undecanoic acid, lauric acid, myristic acid, palmitic acid, palmitooleic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid and the like.
  • At least one of these monovalent fatty acids is properly mixed and esterified with pentaerythritol or its condensate to obtain an ester satisfying desirable physical properties required for various refrigerators.
  • the amount of the straight or branched-chain fatty acid used is preferable to be not less than 50 mol% per the total monovalent fatty acid used.
  • At least one polybasic acid having a carbon number of 4-36 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 same polybasic acids as described in the first invention are used in the same manner as in the first invention.
  • ester compounds according to the second invention can be obtained by the same method as in the first invention.
  • the acid value is preferable to be not more than 3 and the hydroxyl value is preferable to be not more than 50 likewise the case of the first invention.
  • the lubricant for refrigerant HFC-134a and the like according to the third invention comprises an ester obtained by esterifying a polyvalent alcohol represented by the aforementioned general formula (II) with at least one straight or branched-chain monovalent fatty acid having a carbon number of 2-18 and not more than 25 mol% per total fatty acid of at least one polybasic acid having a carbon number of 4-36 as a main component.
  • a polyvalent alcohol represented by the aforementioned general formula (II) with at least one straight or branched-chain monovalent fatty acid having a carbon number of 2-18 and not more than 25 mol% per total fatty acid of at least one polybasic acid having a carbon number of 4-36 as a main component.
  • the carbon number of the monovalent fatty acid when the carbon number of the monovalent fatty acid is more than 18, it becomes very poor in the compatibility of the resulting synthesized ester with HFC-134a and the like.
  • the straight or branched-chain monovalent fatty acids having a carbon number of 3-10 are preferable.
  • the monovalent fatty acid mention may be made of the same compounds as described in the second invention.
  • the polybasic acid having a carbon number of not more than 3 is a special product and is difficult to be cheaply available and is poor in the stability of the ester after the synthesis. While, when the carbon number exceeds 36, the compatibility of the resulting ester with HFC-134a and the like is largely lowered. Therefore, the carbon number of the polybasic acid is preferable to be 4-36, and particularly the carbon number of 4-10 is favorable for ensuring the compatibility with HFC-134a at a wide range.
  • the polybasic acid mention may be made of adipic acid, azelaic acid, sebacic acid and so on.
  • the monovalent fatty acid is 2-ethylhexanoic acid
  • the polybasic acid is adipic acid.
  • the reason why the amount of the polybasic acid added in the invention is limited to not more than 25 mol% per the total fatty acid is due to the fact that when it exceeds 25 mol% the gelation may be caused and it is difficult to obtain desirable physical properties.
  • the ester compounds according to the third invention can be obtained by the same method as in the first and second inventions. In any case, it is desirable that the ester does not contain carboxyl group.
  • the esters according to 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 refrigeration lubricants comprising the ester according to the invention as a main component can solve the problems on the compatibility with HFC-134a and the hygroscopicity, which have never been solved in the conventional technique, and can further enhance the electric insulating property, which comes into problem when HFC-134a is used in a compressor for a refrigerator.
  • additives usually used in the lubri­cant such as antioxidant, anti-wear agent, epoxy compound and the like may properly be added to the refrigeration lubricant according to 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 was 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.
  • Table 2 Type Trade name Color (ASTM) Dynamic viscosity at 40°C (cSt) B-1 PAG 1 Adekapol M-30 1) L 0.5 32.8 B-2 PAG 1 Adekapol M-110 2) L 0.5 105.2 B-3 PAG 1 Adekapol MH-50 3) L 0.5 54.6 C-1 ester dioctyl sebacate L 0.5 11.4 C-2 ester Unistar MB-816 4) L 0.5 8.1 1) polyoxypropylene glycol monoalkyl ether 2) polyoxypropylene glycol monoalkyl ether 3) polyoxyethylene propylene glycol monoalkyl ether 4) monoester of 2-ethylhexanol and palmitic acid Table 3 Test lubricant Dielectric constant at 80°C ( ⁇ cm) Two-phase separation temperature (°C) Seizuring load (Kgf) Thermal stability Hygroscopicity (water content, ppm) low temperature high temperature refrigerant R-12 refriger
  • the electric insulating property represented by the dielectric constant is 100,000 times or more and the two-phase separation at a high temperature is not caused. Furthermore, the seizuring load is excellent and the hygroscopicity is low.
  • the thermal stability is equal in case of the HFC-134a system, but is considerably excellent in case of the R-12 system. This is very advantageous in practical use because the mixing of HFC-134a and R-12 is not avoided at a stage of replacing the refrigerant from R-12 to HFC-134a.
  • esters according to the invention are compared with the commercially available esters (C-1 - C-2), the two-phase separation temperature is extremely different and the conventional esters are insoluble in HFC-134a. In this point, the molecule designed esters according to the invention have a great merit.
  • the esters according to the invention are fairly excellent in the performances as a lubricant as compared with Comparative Examples.
  • esters according to the invention are compared with the commercially available esters (C-1 - C-2) 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 according to the invention have a great merit.
  • the esters according to the invention are fairly excellent in the performances as a lubricant as compared with Comparative Examples.
  • the HFC-134a has been mentioned as a possible replacement for R-12 and is used for car air conditioner, refrigerator and the like. Particularly, in case of the car air conditioner, the compressor is driven in summer season, so that the compatibility between oil and refrigerant at high temperature becomes important. When the two-phase separation between oil and refrigerant is caused in the compressor during the driving, 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 according to 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 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 esters A-10, A-11 and A-12 are particularly suitable therefor.
  • lubricants having a dynamic viscosity of 80-150 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-9, A-13, A-14, A-16 and A-17 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 according to 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 an 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)
EP89119265A 1989-07-05 1989-10-17 Kältemaschinenschmiermittel Expired - Lifetime EP0406479B2 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP91121100A EP0480479B2 (de) 1989-07-05 1989-10-17 Vervendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden
EP92121965A EP0536814B1 (de) 1989-07-05 1989-10-17 Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden.
EP91121101A EP0479338B1 (de) 1989-07-05 1989-10-17 Verwendung eines Schmierstoffs für Kompressoren, die ein chlorfreies Fluorkohlenwasserstoff-Kältemittel verwenden.

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

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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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EP0499994A1 (de) * 1991-02-19 1992-08-26 DEA Mineraloel Aktiengesellschaft Schmiermittel für Kältemaschinen
EP0501440A1 (de) * 1991-02-26 1992-09-02 Kao Corporation Zusammensetzung zur Verwendung als Arbeitsflüssigkeit für Kältemaschinen
EP0518567A1 (de) * 1991-06-07 1992-12-16 Hatco Corporation Aus mit einem hohen Gehalt an verzweigten kettigen Säurenmischungen hergestellte synthetische Grundschmieröle
EP0536940A2 (de) * 1991-10-11 1993-04-14 Imperial Chemical Industries Plc Arbeitsmittelzusammensetzung
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EP0568349A1 (de) * 1992-04-28 1993-11-03 The Lubrizol Corporation Carbonsaüreester enthaltende flüssige Zusammensetzungen
WO1993024597A1 (en) * 1992-06-03 1993-12-09 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
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US5355695A (en) * 1992-11-30 1994-10-18 Mitsubishi Denki Kabushiki Kaisha Refrigeration device using hydrofluorocarbon refrigerant
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KR0131016B1 (ko) 1998-04-14
EP0480479B1 (de) 1997-03-26
DE68927916T3 (de) 2005-03-10
EP0480479A2 (de) 1992-04-15
EP0479338B1 (de) 1997-08-27
EP0479338A3 (en) 1992-05-27
KR910003077A (ko) 1991-02-26
KR970078832A (ko) 1997-12-12
DE68927916D1 (de) 1997-04-30
DE68928281T2 (de) 1998-01-15
DE68925537D1 (de) 1996-03-07
DE68925537T2 (de) 1996-07-04
DE68914448D1 (de) 1994-05-11
EP0406479B1 (de) 1994-04-06
KR0131017B1 (ko) 1998-04-14
ES2082341T3 (es) 1996-03-16
EP0480479A3 (en) 1992-06-17
DE68914448T3 (de) 2003-03-06
EP0536814A1 (de) 1993-04-14
ES2099120T3 (es) 1997-05-16
ES2104650T3 (es) 1997-10-16
DE68914448T2 (de) 1994-08-25
KR970078831A (ko) 1997-12-12
SG49165A1 (en) 1998-05-18
SG49157A1 (en) 1998-05-18
DE68927916T2 (de) 1997-08-21
EP0479338A2 (de) 1992-04-08
EP0480479B2 (de) 2004-09-01
KR950005694B1 (ko) 1995-05-29
ES2051340T3 (es) 1994-06-16
EP0406479B2 (de) 2002-09-04

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