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WO1992015658A1 - Lubrifiants pour installations de transfert de chaleur - Google Patents

Lubrifiants pour installations de transfert de chaleur Download PDF

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Publication number
WO1992015658A1
WO1992015658A1 PCT/GB1992/000379 GB9200379W WO9215658A1 WO 1992015658 A1 WO1992015658 A1 WO 1992015658A1 GB 9200379 W GB9200379 W GB 9200379W WO 9215658 A1 WO9215658 A1 WO 9215658A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
working fluid
cst
polyalkoxylate
heat transfer
Prior art date
Application number
PCT/GB1992/000379
Other languages
English (en)
Inventor
Allan Stewart
Philip Michael Stroud
John Eastwood
Robert Ian George Thompson
Original Assignee
Imperial Chemical Industries Plc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Plc filed Critical Imperial Chemical Industries Plc
Publication of WO1992015658A1 publication Critical patent/WO1992015658A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00Lubricating 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
    • C10M171/008Lubricant compositions compatible with refrigerants
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00Heat-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
    • C09K5/02Materials undergoing a change of physical state when used
    • C09K5/04Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041Materials 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
    • C09K5/044Materials 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
    • C09K5/045Materials 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
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/40Lubricating compositions characterised by the base-material being a macromolecular compound containing nitrogen
    • C10M107/44Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24Only one single fluoro component present
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06Perfluorinated compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/30Refrigerators lubricants or compressors lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/32Wires, ropes or cables lubricants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/34Lubricating-sealants
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/36Release agents or mold release agents
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/38Conveyors or chain belts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/40Generators or electric motors in oil or gas winning field
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/42Flashing oils or marking oils
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/44Super vacuum or supercritical use
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/50Medical uses

Definitions

  • This invention relates to lubricants and more particularly to their use in heat transfer devices.
  • 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 dichlorodifluoromethane (R-12) 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 equip ⁇ umt, it is necessary for the moving parts
  • the devices are generally designed to use lubricants which are miscible with the working fluids, mineral oil being used in conjunction with dichlorodifluoromethane.
  • MAC mobile air-conditioning
  • the upper miscibility temperature the maximum temperature
  • the miscibility of the lubricant is often at a level intermediate to that of the 4 - ⁇ miscibility of the lubricant in the individual components.
  • certain refrigeration systems e.g. automobile air conditioning systems, are often designed so as to require the lubricant to have an intrinsic viscosity at 100°C within a specific range of viscosities, e.g. 9 to 10 cSt, or 14 to 16 cSt, or 20 to 22 cSt.
  • a lubricant having an intrinsic viscosity in the range 9 to lOcSt is generally not suitable for use in a system requiring a 14 to 16 cSt lubricant.
  • Polyalkoxylates such as polyalkylene glycols (PAGs) having -OH and other terminal groups have been proposed as alternatives.
  • PAGs polyalkylene glycols
  • Such materials have been prepared which have miscibility temperatures in excess of 70°C and also intrinsic viscosities of between 9 to 10 cSt.
  • materials which have hitherto been prepared having satisfactory intrinsic viscosities in the range 14 to 16 cSt have miscibility temperatures significantly lower than 70°C.
  • polyalkoxylates as defined below are excellent lubricants when used with a working fluid such as 1,1,1,2-tetrafluoroethane, related hydro- fluorocarbons such as 1,1,2,2-tetra fluoroethane, and hydrochlorofluorocarbons such as monochlorotetrafluoroethane.
  • a working fluid such as 1,1,1,2-tetrafluoroethane, related hydro- fluorocarbons such as 1,1,2,2-tetra fluoroethane, and hydrochlorofluorocarbons such as monochlorotetrafluoroethane.
  • Such polyalkoxylates have in combination an intrinsic viscosity of at least 14 cSt at 100°C and an improved miscibility with the working fluid compared with known polyalkoxylate lubricants.
  • the invention provides a composition for use in a compression type heat transfer device comprising a working fluid and sufficient to provide lubrication of a polyalkoxylate, wherein the working fluid comprises at least one hydrofluoroalkane or fluoroalkane and the polyalkoxylate has an intrinsic viscosity at 100°C of at least 14 cSt, has an upper miscibility temperature of at least 55°C at a weight ratio of 1:9 in the working fluid and comprises a nitrogen compound residue initiating a polyoxyalkylene chain which is terminated by an end capping group.
  • the invention further provides a method of lubricating a compression type heat transfer device wherein the surfaces of the relatively moveable components of the device are contacted with a composition as defined above.
  • the working fluid may be one or more refrigerants selected from the group containing R-23, R-32, R-134a, R-152a, R-134, and R-143, and optionally one or more refrigerants selected from the group containing R-125, R-22, R-124, R-124a, R-142a, R-133, R-123, and R-123a.
  • Compositions of the present invention preferably contain a working fluid comprising R-134a, e.g. R-134a in combination with R32 and/or R-125.
  • such materials have an intrinsic viscosity at 100°C of at least 14 cSt, and preferably in the range 14 to 16 cSt, in combination with an upper miscibility temperature (at a weight ratio of 1:9 with the working fluid, i.e. 10Z w/w) of at least 55°C, preferably at least 58°C, and most suitably in the range 55 to 75°C.
  • the initiating nitrogen compound residue is preferably the residue formed by the removal of at least one active hydrogen atom from ammonia, or an organic amine or amide.
  • the nitrogen compound may be a mono or polyhydric amine having primary and/or secondary amine groups.
  • the nitrogen compound may thus be selected from alkyl, cycloalkyl or aromatic amines and amides having 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms and more preferably 1 to 15 carbon atoms and preferably 1 to 100, more preferably 1 to 10 and most preferably 1 to 6 amine or amide groups.
  • suitable nitrogen compounds include alkylamines, alkylene diamines and in particular piperazine.
  • the polyoxyalkylene chain may comprise 4 to 170, preferably 5 to 140, and particularly 5 to 120 alkylene oxide residues, each having 2 to 4 carbon atoms.
  • the polyoxyalkylene chain may contain one or more species of alkylene oxide. Thus, where more than one species of alkylene oxide is present, for example where both propylene oxide and ethylene oxide residues are present.
  • the polyoxyalkylene chain may have the structure of a random or block polymer.
  • Preferred polyoxyalkylene chains are those which contain 0 to 70 mol Z, particularly 0 to 60 mol Z, and especially 0 to 50 mol Z of ethylene oxide residues with the complementary percentage of propylene oxide residues.
  • the end capping group may be provided by an alkyl, or aryl, or aralkyl group.
  • the end capping group is one or more methyl, ethyl, propyl, isopropyl, or butyl groups.
  • R- ⁇ represents the nitrogen compound residue having n active sites
  • P represents the polyoxyalkylene chain
  • R ⁇ represents the end capping group or groups.
  • the polyalkoxylate used in the present invention may be any polyalkoxylate used in the present invention.
  • the reaction of the nitrogen compound and alkylene oxide moieties may be conducted in one or more stages, and is usually
  • the temperature of the reaction is preferably controlled to be in the range 100 to 180°C, preferably 150 to 160°C for ethoxylation, 105 to 130°C, e.g. 125°C, for propoxylation or butoxylation, or 105 to 130°C, e.g. 105°C for
  • the reaction is preferably conducted at a controlled elevated pressure, in particular at a pressure of 1.5 to 8 bars absolute.
  • the subsequent endcapping of the terminal alkyle-ie oxide residues is usually achieved by reaction with a suitable derivative of the end capping group, for example where it is desired to end cap using a methyl group then methyl chloride is usually used in conjunction with a metal alkoxide, e.g. sodium methoxide.
  • a metal alkoxide e.g. sodium methoxide.
  • an acidic passivating agent e.g. phosphoric acid
  • aqueous solution containing 860 g of potassium hydroxide and 546 g of water was added to 18 kg of piperazine.
  • the resulting mixture was then dehydrated by heating to a temperature between 120 and 125°C, under a vacuum of between 5 to 15 mm Hg for about 0.5 hours in an autoclave. Nitrogen was bubbled through the dehydrated mixture thereby increasing the pressure in the autoclave to 2 bars absolute.
  • the propylene oxide was then added in two stages. In the first stage 20.6 kg propylene oxide was introduced into the autoclave over a period of 1.5 hours, whilst maintaining the temperature at 125°C. The pressure within the autoclave increased from 2.4 to 2.8 bars absolute during this period. After the propylene oxide had been added the reaction was continued for 4 hours, whereupon the product was vacuum stripped of unreacted propylene oxide at a temperature of 110°C, and a pressure of between 5 to 15 mm Hg, for 1.5 hours.
  • the material as produced above was then endcapped with methyl groups in the following manner.
  • 70 kg of the piperazine propoxylate was mixed with 7 kg of sodium methoxide and stirred for 0.5 hours at ambient temperature.
  • the resulting mixture was then heated to 120°C under a vacuum of 27 mbar, whilst continuing to be stirred for a period of 5 hours.
  • the pressure was then increased to 1 bar absolute using nitrogen at which point 7.2 kg of methyl chloride was introduced into the reactor over a period of 2.5 hours, whilst maintaining the temperature of the reactor at between 120 to 130°C.
  • the reaction was then continued at a temperature of 120°C for 1 hour.
  • the product was then vacuum stripped for a period of 0.75 hour as described above whereupon the pressure in the reactor was increased to 1 bar absolute using nitrogen.
  • the dehydrated product was then demineralised using 1 kg of "Ambosol” (magnesium silicate), and 1 kg of “Dicalite” (filter aid).
  • the resulting mixture was heated to 110°C for 1.5 hours, then filtered at a temperature of 110°C using a Gauthier filter to produce a final product.
  • the yield of the final product was 60 kg.
  • the final product was identified as a substantially (approximately 95Z) methyl end capped piperazine propoxylate, having a molecular weight of about 1328.
  • the viscosity of the product at 40°C was 76.3 cSt, at 100°C was 14.1 cSt, thereby giving a viscosity index (VI) of 193.
  • a mixture containing 5Z w/w of the product and 95Z w/w of refrigerant R-134a had an upper miscibility temperature of 60°C, and a mixture containing 10Z w/w of the product and 90Z w/w of the refrigerant had an upper miscibility temperature of 58°C.
  • a number of known propoxylate lubricants were prepared and tested.
  • Comparative examples Cl to C6 were initiated on methanol, C7 on butanol and C8 to C9 on glycerol.
  • the polyalkylene chain in all cases contained propylene oxide repeat units, and the end capping groups in C2, C4 and C6 to C9 were methyl.
  • the properties of these known propoxylate lubricantss are displayed in Table 1.
  • Propoxylates C8 and C9 show that increasing the number of polyoxypropylene chains, which was achieved by using an initiator (glycerol) having more than one hydroxy group, slightly improves the upper miscibility temperature.
  • the known propoxylates in Cl to C9 do not possess the combination of desired intrinsic viscosity and upper miscibility temperature.

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

Abstract

Composition réfrigérante contenant un fluide moteur fluoro ou hydrofluroalcane et en tant que lubrifiant un polyalcoxylate à coiffe terminale amorcé par une amine, par ex. un polypropylène à coiffe terminale de méthyle amorcé par une pipérazine. Ledit lubrifiant possède une viscosité intrinsèque d'au moins 14 cSt à 100 °C et une température supérieure de miscibilité d'au moins 55 °C à un rapport pondéral de 1:9 avec le fluide moteur.
PCT/GB1992/000379 1991-03-05 1992-03-04 Lubrifiants pour installations de transfert de chaleur WO1992015658A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919104588A GB9104588D0 (en) 1991-03-05 1991-03-05 Lubricants
GB9104588.0 1991-03-05

Publications (1)

Publication Number Publication Date
WO1992015658A1 true WO1992015658A1 (fr) 1992-09-17

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ID=10690992

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Application Number Title Priority Date Filing Date
PCT/GB1992/000379 WO1992015658A1 (fr) 1991-03-05 1992-03-04 Lubrifiants pour installations de transfert de chaleur

Country Status (3)

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AU (1) AU1414692A (fr)
GB (1) GB9104588D0 (fr)
WO (1) WO1992015658A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993018110A1 (fr) * 1992-03-03 1993-09-16 University Of Moncton Melange refrigerant non azeotrope de r23, r125 et r32

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4851144A (en) * 1989-01-10 1989-07-25 The Dow Chemical Company Lubricants for refrigeration compressors
US4900463A (en) * 1989-05-23 1990-02-13 Allied-Signal Inc. Refrigeration lubricant blends
WO1990007562A1 (fr) * 1988-12-27 1990-07-12 Allied-Signal Inc. Compositions fluorurees de lubrification
EP0379175A1 (fr) * 1989-01-18 1990-07-25 The Dow Chemical Company Lubrifiants à base de polyglycol pour compresseurs frigorifiques et leur procédé de préparation
US4959169A (en) * 1989-10-20 1990-09-25 The Dow Chemical Company Esterified polyglycol lubricants for refrigeration compressors
EP0415626A1 (fr) * 1989-08-29 1991-03-06 Imperial Chemical Industries Plc Lubrification et lubrifiants

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990007562A1 (fr) * 1988-12-27 1990-07-12 Allied-Signal Inc. Compositions fluorurees de lubrification
US4851144A (en) * 1989-01-10 1989-07-25 The Dow Chemical Company Lubricants for refrigeration compressors
EP0379175A1 (fr) * 1989-01-18 1990-07-25 The Dow Chemical Company Lubrifiants à base de polyglycol pour compresseurs frigorifiques et leur procédé de préparation
US4900463A (en) * 1989-05-23 1990-02-13 Allied-Signal Inc. Refrigeration lubricant blends
EP0415626A1 (fr) * 1989-08-29 1991-03-06 Imperial Chemical Industries Plc Lubrification et lubrifiants
US4959169A (en) * 1989-10-20 1990-09-25 The Dow Chemical Company Esterified polyglycol lubricants for refrigeration compressors

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993018110A1 (fr) * 1992-03-03 1993-09-16 University Of Moncton Melange refrigerant non azeotrope de r23, r125 et r32

Also Published As

Publication number Publication date
GB9104588D0 (en) 1991-04-17
AU1414692A (en) 1992-10-06

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