GB2216541A - Working fluid/lubricant combination - Google Patents

Working fluid/lubricant combination Download PDF

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Publication number
GB2216541A
GB2216541A GB8905795A GB8905795A GB2216541A GB 2216541 A GB2216541 A GB 2216541A GB 8905795 A GB8905795 A GB 8905795A GB 8905795 A GB8905795 A GB 8905795A GB 2216541 A GB2216541 A GB 2216541A
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United Kingdom
Prior art keywords
ester
combination according
working fluid
lubricant
phthalate
Prior art date
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Granted
Application number
GB8905795A
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GB2216541B (en
GB8905795D0 (en
Inventor
Richard Llewellyn Powell
Gordon Tompsett
Melvin Conlong
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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Publication of GB8905795D0 publication Critical patent/GB8905795D0/en
Publication of GB2216541A publication Critical patent/GB2216541A/en
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Publication of GB2216541B publication Critical patent/GB2216541B/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
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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    • 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
    • C10M105/36—Esters of polycarboxylic acids
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    • 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
    • C10M105/38—Esters of polyhydroxy compounds
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
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    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
    • C10M131/04—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only aliphatic
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/10—Components
    • C09K2205/12—Hydrocarbons
    • C09K2205/122—Halogenated hydrocarbons
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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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
    • C10N2040/40—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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)

Abstract

A working fluid/lubricant combination for use in a mechanical vapour recompression type heat transfer device wherein the working fluid comprises a hydrofluorocarbon, hydrochlorofluorocarbon or chlorofluorocarbon and the lubricant comprises an ester having a molecular weight greater than 250.

Description

LUBRICANTS This invention relates to lubricants and more particularly to their use in heat transfer devices.
Heat transfer devices of the mechanical vapour recompression type, including refrigerators, heat pumps and air conditioning systems, are well known. In such devices, a working fluid of suitable boiling point evaporates at low pressure taking heat from the surrounding zone. The resulting vapour is then compressed and passed to a condenser where it condenses and gives off heat to a second zone. The condensate is then returned through an expansion valve to the evaporator, so completing the cycle. The mechanical energy required for compressing the vapour and pumping the fluid is provided by, for example, an electric motor or an internal combustion engine.
The working fluids used in these heat transfer devices include chlorofluorocarbons such as dichlorodifluoromethane the production of which is likely to be severely limited by international agreement in order to protect the stratospheric ozone layer. As is the case with other mechanical equipment, it is necessary for the moving parts of the heat transfer devices to be adequately lubricated and the devices are generally designed to use lubricants which are miscible with the working fluids, mineral oil commonly being used in conjunction with dichlorodifluoromethane.
Unfortunately some of the compounds, for example 1,1,1,2-tetrafluoroethane, which have been proposed as working fluids to replace dichlorodifluoromethane are insufficiently soluble in mineral oils to allow the latter to be used as lubricants. Polyalkylene glycols have been proposed as alternatives but they are not entirely satisfactory for a number of reasons . Thus, whilst they show reverse solubility such that the wo king fluid tends to separate from the lubricant at temperatures above about 400C, they often attract water to an extent sufficient to cause corrosion in the equipment. Furthermore, they often fail to wet metals sufficiently to provide efficient lubrication and have an adverse effect on aluminium commonly used for the construction of compressors.
It has now been found that esters having molecular weights greater than about 250 are excellent lubricants having adequate miscibility with 1,1,1,2-tetrafluoroethane and some related hydrofluorocarbon working fluids such as 1,1,2,2-tetrafluoroethane, and hydrochlorofluorocarbons such as the monochlorotetrafluoroethanes and are free from the disadvantages associated with polyalkylene glycols. The esters can also be used in conjunction with chlorofluorocarbons such as monochlorodifluoromethane and dichlorodifluoromethane Accordingly, the esters can be used in heat transfer devices with dichlorodifluoromethane so long as that working fluid is available and can then be used with one of its replacements, for example 1,1,1,2-tetrafluoroethane.Furthermore, the esters can be used in conjunction with dichlorodifluoromethane/1, 1,1, 2-tetra- fluoroethane mixtures.
Thus, the invention provides a working fluid/lubricant combination for use in a mechanical vapour recompression type heat transfer device wherein the working fluid comprises a hydrofluorocarbon, hydrochlorofluorocarbon or chlorofluorocarbon and the lubricant comprises an ester having a molecular weight greater than 250.
Suitable esters include compounds containing from one to three or even more ester groups. Suitable classes of esters include: (1) alkyl esters of aliphatic carboxylic acids, for example di(2-ethylhexyl) adipate, (2) alkyl esters of aromatic carboxylic acids, for example tetrabutyl pyromellitate, (3) alkoxyalkyl and alkoxyalkoxyalkyl esters of aliphatic carboxylic acid, for example di (methoxyethoxyethyl) adipate, (4) alkoxyalkyl and alkoxyalkoxyalkyl esters of aromatic carboxylic acids, for example di(methoxyethyl) phthalate, di(butoxyethyl) phthalate, di(butoxyethoxyethyl) phthalate and tetra(butoxyethyl) pyromellitate, and (5) glycol di-ester of aromatic carboxylic acids, for example dipropylene glycol benzoate.
Mixtures of esters may be used if desired as may mixtures of one or more esters with one or more polyalkylene glycols.
The esters described above are sufficiently miscible with 1,1,1,2-tetrafluoroethane and related working fluids to enable their use as working fluid/lubricant combinations in mechanical vapour recompression type heat transfer devices. For this purpose the solubility of the lubricant in the working fluid should be at least 15% by weight over a temperature range of from -40 to +800C.
Solubilities of various esters in 1,1,1,2-tetrafluoroethane are as shown in the following Table.
TABLE
Room Temperature < 0 C 55 C Lubricant 50% w/w 33% w/w 20% w/w 10% w/w 20% w/w 10% w/w 20% w/w 10% w/w Lubricant Lubricant Lubricant Lubricant Lubricant Lubricant Lubricant Lubricant POLYESTERS Dipropylene Glycol Benzoate MIS MIS MIS MIS MIS MIS MIS MIS Di (methoxyethoxyethyl)Adipate MIS MIS MIS MIS MIS MIS MIS MIS Di (methoxyethyl)Phthalate MIS MIS MIS MIS MIS MIS MIS MIS Di (butoxyethyl)Phthalate MIS MIS MIS MIS MIS MIS MIS MIS Di (2-ethylhexyl)Adipate MIS MIS MIS Bis-2-(2-Butoxyethoxy) Ethyl Phthalate MIS MIS MIS MIS Tetra (butoxyethyl) Pyromellitate MIS MIS MIS MIS MIS MIS MIS MIS

Claims (12)

  1. CLAIMS 1. A working fluid/lubricant combination for use in a mechanical vapour recompression type heat transfer device wherein the working fluid comprises a hydrofluorocarbon, hydrochlorofluorocarbon or chlorofluorocarbon and the lubricant comprises an ester having a molecular weight greater than 250.
  2. 2. A combination according to claim 1 wherein the working fluid comprises a tetrafluoroethane
  3. 3. A combination according to claim 1 or claim 2 wherein the working fluid comprises monochlorodifluoromethane or dichlorodifluoromethane.
  4. 4. A combination according to any preceding claim wherein the working fluid comprises a mixture of dichlorodifluoromethane and 1,1,1,2-tetrafluoroethane.
  5. 5. A combination according to any preceding claim wherein the ester contains from one to three ester groups.
  6. 6. A combination according to claim 5 wherein the ester is an alkyl ester of an aliphatic or aromatic carboxylic acid.
  7. 7. A combination according to claim 6 wherein the ester is di(2-ethylhexyl) adipate or tetrabutyl pyromellitate.
  8. 8. A combination according to claim 5 wherein the ester is an alkoxyalkyl or alkoxyalkoxyalkyl ester of an aliphatic or aromatic carboxylic acid.
  9. 9. A combination according to claim 8 wherein the ester is selected from di(methoxyethoxyethyl) adipate, di(methoxyethyl) phthalate, di(butoxyethyl) phthalate, di(butoxyethoxyethyl)phthalate, and tetra(butoxyethyl) pyromellitate.
  10. 10. A combination according to claim 5 wherein the ester is a glycol di-ester of an aromatic carboxylic acid.
  11. 11. A combination according claim 10 wherein the ester is dipropylene glycol benzoate.
  12. 12. A combination according to claim 1 substantially as hereinbefore described.
GB8905795A 1988-03-23 1989-03-14 Working fluid/lubricant combination Expired - Lifetime GB2216541B (en)

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GB888806923A GB8806923D0 (en) 1988-03-23 1988-03-23 Lubricants

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GB2216541A true GB2216541A (en) 1989-10-11
GB2216541B GB2216541B (en) 1991-10-23

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Cited By (29)

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Publication number Priority date Publication date Assignee Title
EP0378176A1 (en) * 1989-01-10 1990-07-18 The Dow Chemical Company Lubricants for refrigeration compressors
WO1990012849A1 (en) * 1989-04-25 1990-11-01 The Lubrizol Corporation Liquid compositions containing carboxylic esters
EP0415778A1 (en) * 1989-09-01 1991-03-06 Kao Corporation Refrigeration oil composition
US5002678A (en) * 1990-06-29 1991-03-26 Olin Corporation Lubricants for heat transfer fluids
EP0426153A1 (en) * 1989-11-02 1991-05-08 Mitsui Petrochemical Industries, Ltd. Use of glycol ether carbonate as refrigeration lubricant
US5021179A (en) * 1990-07-12 1991-06-04 Henkel Corporation Lubrication for refrigerant heat transfer fluids
EP0435253A1 (en) * 1989-12-28 1991-07-03 Nippon Oil Company, Limited Refrigerator oils for use with hydrogen-containing halogenocarbon refrigerants
EP0440069A1 (en) * 1990-01-22 1991-08-07 Kao Corporation Refrigeration oil composition
EP0445610A1 (en) * 1990-03-05 1991-09-11 Hoechst Aktiengesellschaft Use of complex ester oils as lubricant for refrigerant compressor
EP0445611A1 (en) * 1990-03-05 1991-09-11 Hoechst Aktiengesellschaft Use of ester oils as lubricant for refrigerant compressor
EP0449406A1 (en) * 1990-01-31 1991-10-02 Tonen Corporation Esters as lubricants for a haloalkane refrigerant
EP0452509A1 (en) * 1989-11-13 1991-10-23 Idemitsu Kosan Company Limited Use of synthetic lubricating oil based on polyester as lubricant in refrigerators
EP0458584A1 (en) * 1990-05-22 1991-11-27 Unichema Chemie B.V. Lubricants
EP0461262A1 (en) * 1989-12-14 1991-12-18 Idemitsu Kosan Company Limited Use of refrigerator oil composition for Hydrofluorcarbon refrigerant
EP0461435A1 (en) * 1990-06-09 1991-12-18 Hoechst Aktiengesellschaft Application of aromatic carboxylic esters as lubricant in refrigerant compressors
EP0468729A1 (en) * 1990-07-23 1992-01-29 Castrol Limited Lubrication of vapour compression heat transfer systems
EP0475751A1 (en) * 1990-09-12 1992-03-18 Kao Corporation Working fluid composition for refrigerating machine
WO1992006147A1 (en) * 1990-10-09 1992-04-16 Imperial Chemical Industries Plc Lubricants
EP0523561A1 (en) * 1991-07-17 1993-01-20 Idemitsu Kosan Company Limited Lubricating oil composition
US5240629A (en) * 1992-01-10 1993-08-31 Ethyl Corporation Refrigerant compositions
EP0580308A1 (en) 1992-07-04 1994-01-26 Kao Corporation Working fluid composition for refrigeration machine
US5470497A (en) * 1992-12-17 1995-11-28 Exxon Chemical Patents Inc. Refrigeration working fluid compositions containing trifluoroethane and neopentyl glycol or trimethylolpropane esters of C7 and C9 acids
US5494597A (en) * 1993-01-07 1996-02-27 Exxon Chemical Patents Inc. Refrigeration working fluid compositions containing difluoroethane or pentafluoroethane and a polyolester lubricant
EP0704521A1 (en) * 1994-09-19 1996-04-03 Hüls America Inc. Method for removing unwanted lubricating oil from a refrigeration system
US5575944A (en) * 1992-08-11 1996-11-19 Kao Corporation Acetal-containing working fluid composition for refrigerating machine
US5798319A (en) * 1996-01-16 1998-08-25 Exxon Chemical Patents Inc. High stability and low metals esters based on 3,5,5-trimethyl-1-hexanol
WO2003025105A1 (en) * 2001-09-19 2003-03-27 3M Innovative Properties Company Composition comprising lubricious additive for cutting or abrasive working and a method therefor
US6582621B1 (en) * 1989-12-28 2003-06-24 Nippon Mitsubishi Oil Corporation Refrigerator oils for use with chlorine-free fluorocarbon refrigerants
WO2019108720A1 (en) * 2017-11-30 2019-06-06 The Lubrizol Corporation Aromatic ester lubricant for use with low global warming potential refrigerants

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ATE194641T1 (en) 1992-06-03 2000-07-15 Henkel Corp POLYOLESTER AS A LUBRICANT FOR HIGH TEMPERATURE REFRIGERANT COMPRESSORS
ATE184310T1 (en) 1992-06-03 1999-09-15 Henkel Corp POLYOL/ESTER MIXTURE AS A LUBRICANT FOR HEAT TRANSFER FLUIDS IN REFRIGERANT SYSTEMS
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
WO1993024585A1 (en) 1992-06-03 1993-12-09 Henkel Corporation Polyol ester lubricants for refrigerant heat transfer fluids
AU699190B2 (en) 1994-05-23 1998-11-26 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0378176A1 (en) * 1989-01-10 1990-07-18 The Dow Chemical Company Lubricants for refrigeration compressors
WO1990012849A1 (en) * 1989-04-25 1990-11-01 The Lubrizol Corporation Liquid compositions containing carboxylic esters
AU638710B2 (en) * 1989-04-25 1993-07-08 Lubrizol Corporation, The Liquid compositions containing carboxylic esters
EP0415778A1 (en) * 1989-09-01 1991-03-06 Kao Corporation Refrigeration oil composition
US5096606A (en) * 1989-09-01 1992-03-17 Kao Corporation Refrigeration oil composition containing a fluoroethane and an ester compound
EP0426153A1 (en) * 1989-11-02 1991-05-08 Mitsui Petrochemical Industries, Ltd. Use of glycol ether carbonate as refrigeration lubricant
EP0452509A1 (en) * 1989-11-13 1991-10-23 Idemitsu Kosan Company Limited Use of synthetic lubricating oil based on polyester as lubricant in refrigerators
EP0452509A4 (en) * 1989-11-13 1992-04-01 Idemitsu Petrochemical Co. Ltd. Synthetic lubricating oil based on polyester
US5403503A (en) * 1989-12-14 1995-04-04 Idemitsu Kosan Co., Ltd. Refrigerator oil composition for hydrogen-containing hydrofluorocarbon refrigerant
EP0461262A1 (en) * 1989-12-14 1991-12-18 Idemitsu Kosan Company Limited Use of refrigerator oil composition for Hydrofluorcarbon refrigerant
EP0461262A4 (en) * 1989-12-14 1992-03-18 Idemitsu Kosan Company Limited Refrigerator oil composition for hydrofluorocarbon refrigerant
US6582621B1 (en) * 1989-12-28 2003-06-24 Nippon Mitsubishi Oil Corporation Refrigerator oils for use with chlorine-free fluorocarbon refrigerants
EP0435253A1 (en) * 1989-12-28 1991-07-03 Nippon Oil Company, Limited Refrigerator oils for use with hydrogen-containing halogenocarbon refrigerants
EP0440069A1 (en) * 1990-01-22 1991-08-07 Kao Corporation Refrigeration oil composition
EP0449406A1 (en) * 1990-01-31 1991-10-02 Tonen Corporation Esters as lubricants for a haloalkane refrigerant
EP0638630A1 (en) * 1990-01-31 1995-02-15 Tonen Corporation Esters as lubricants for a haloalkane refrigerant
EP0629687A1 (en) * 1990-01-31 1994-12-21 Tonen Corporation Esters as lubricants for a haloalkane refrigerant
EP0786510A1 (en) * 1990-01-31 1997-07-30 Exxon Chemical Patents Inc. Esters as lubricants for a haloalkane refrigerant
JPH04218592A (en) * 1990-03-05 1992-08-10 Hoechst Ag Use of ester oil as lubricant of refrigerant compressor
EP0445611A1 (en) * 1990-03-05 1991-09-11 Hoechst Aktiengesellschaft Use of ester oils as lubricant for refrigerant compressor
EP0445610A1 (en) * 1990-03-05 1991-09-11 Hoechst Aktiengesellschaft Use of complex ester oils as lubricant for refrigerant compressor
JPH04220497A (en) * 1990-03-05 1992-08-11 Hoechst Ag Use of complex ester oil as lubricant of refrigerant compressor
EP0458584A1 (en) * 1990-05-22 1991-11-27 Unichema Chemie B.V. Lubricants
US5211884A (en) * 1990-05-22 1993-05-18 Unilever Patent Holdings Bv Lubricants
JPH04226193A (en) * 1990-06-09 1992-08-14 Hoechst Ag Method of use of aromatic carboxylic acid as lubricant of refrigerating compressor
JPH0778229B2 (en) 1990-06-09 1995-08-23 ヘキスト・アクチェンゲゼルシャフト Use of esters of phthalic acid, isophthalic acid or terephthalic acid as lubricants for refrigeration compressors
EP0461435A1 (en) * 1990-06-09 1991-12-18 Hoechst Aktiengesellschaft Application of aromatic carboxylic esters as lubricant in refrigerant compressors
US5002678A (en) * 1990-06-29 1991-03-26 Olin Corporation Lubricants for heat transfer fluids
US5021179A (en) * 1990-07-12 1991-06-04 Henkel Corporation Lubrication for refrigerant heat transfer fluids
GB2247466A (en) * 1990-07-23 1992-03-04 Castrol Ltd Lubricants for heat transfer devices.
JPH04248099A (en) * 1990-07-23 1992-09-03 Castrol Ltd Lubricating method
US5229025A (en) * 1990-07-23 1993-07-20 Castrol Limited Lubrication and a method of retrofilling a working fluid/lubricant composition
EP0468729A1 (en) * 1990-07-23 1992-01-29 Castrol Limited Lubrication of vapour compression heat transfer systems
AU649461B2 (en) * 1990-07-23 1994-05-26 Castrol Limited Lubrication
GB2247466B (en) * 1990-07-23 1994-11-16 Castrol Ltd Retrofilling mechanical vapour recompression heat transfer devices
EP0475751A1 (en) * 1990-09-12 1992-03-18 Kao Corporation Working fluid composition for refrigerating machine
US5202044A (en) * 1990-09-12 1993-04-13 Kao Corporation Working fluid composition for refrigerating machine
WO1992006147A1 (en) * 1990-10-09 1992-04-16 Imperial Chemical Industries Plc Lubricants
EP0523561A1 (en) * 1991-07-17 1993-01-20 Idemitsu Kosan Company Limited Lubricating oil composition
US5240629A (en) * 1992-01-10 1993-08-31 Ethyl Corporation Refrigerant compositions
EP0580308A1 (en) 1992-07-04 1994-01-26 Kao Corporation Working fluid composition for refrigeration machine
US5575944A (en) * 1992-08-11 1996-11-19 Kao Corporation Acetal-containing working fluid composition for refrigerating machine
US5470497A (en) * 1992-12-17 1995-11-28 Exxon Chemical Patents Inc. Refrigeration working fluid compositions containing trifluoroethane and neopentyl glycol or trimethylolpropane esters of C7 and C9 acids
US5494597A (en) * 1993-01-07 1996-02-27 Exxon Chemical Patents Inc. Refrigeration working fluid compositions containing difluoroethane or pentafluoroethane and a polyolester lubricant
EP0704521A1 (en) * 1994-09-19 1996-04-03 Hüls America Inc. Method for removing unwanted lubricating oil from a refrigeration system
US5798319A (en) * 1996-01-16 1998-08-25 Exxon Chemical Patents Inc. High stability and low metals esters based on 3,5,5-trimethyl-1-hexanol
WO2003025105A1 (en) * 2001-09-19 2003-03-27 3M Innovative Properties Company Composition comprising lubricious additive for cutting or abrasive working and a method therefor
US6759374B2 (en) 2001-09-19 2004-07-06 3M Innovative Properties Company Composition comprising lubricious additive for cutting or abrasive working and a method therefor
WO2019108720A1 (en) * 2017-11-30 2019-06-06 The Lubrizol Corporation Aromatic ester lubricant for use with low global warming potential refrigerants

Also Published As

Publication number Publication date
ZA892140B (en) 1990-07-25
GB8806923D0 (en) 1988-04-27
GB2216541B (en) 1991-10-23
GB8905795D0 (en) 1989-04-26

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Legal Events

Date Code Title Description
727 Application made for amendment of specification (sect. 27/1977)
727A Application for amendment of specification now open to opposition (sect. 27/1977)
727B Case decided by the comptroller ** specification amended (sect. 27/1977)
SP Amendment (slips) printed
PE20 Patent expired after termination of 20 years

Expiry date: 20090313