WO1992018580A1 - Compositions de refrigeration contenant un refrigerant hydrofluorocarbure et un lubrifiant - Google Patents

Compositions de refrigeration contenant un refrigerant hydrofluorocarbure et un lubrifiant Download PDF

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Publication number
WO1992018580A1
WO1992018580A1 PCT/US1992/002401 US9202401W WO9218580A1 WO 1992018580 A1 WO1992018580 A1 WO 1992018580A1 US 9202401 W US9202401 W US 9202401W WO 9218580 A1 WO9218580 A1 WO 9218580A1
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WIPO (PCT)
Prior art keywords
lubricant
refrigerant
group
composition
units
Prior art date
Application number
PCT/US1992/002401
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English (en)
Inventor
Raymond Hilton Percival Thomas
Hang Thanh Pham
John Walter Pelava
David Paul Wilson
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Allied-Signal Inc.
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Filing date
Publication date
Application filed by Allied-Signal Inc. filed Critical Allied-Signal Inc.
Publication of WO1992018580A1 publication Critical patent/WO1992018580A1/fr

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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
    • 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
    • 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
    • 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
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
    • 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/22—All components of a mixture being fluoro 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
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24—Only one single fluoro component present
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/042—Epoxides
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/02—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen and halogen only
    • 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
    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • C—CHEMISTRY; METALLURGY
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
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    • C10M2213/00—Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06—Perfluoro polymers
    • C10M2213/062—Polytetrafluoroethylene [PTFE]
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
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    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
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    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
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    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • C10M2229/051—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing halogen
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    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
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    • C10N2040/32—Wires, ropes or cables lubricants
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    • C10N2040/36—Release agents or mold release agents
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    • C10N2040/40—Generators or electric motors in oil or gas winning field
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    • C10N2040/42—Flashing oils or marking oils
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses

Definitions

  • the present invention relates to novel refrigeration compositions. More particularly, the present invention relates to novel refrigeration compositions wherein the refrigerant is difluoromethane (known in the art as R32) or pentafluoroethane (known in the art as R125) .
  • R32 and R125 is a refrigerant which may replace dichlorodifluoromethane (known in the art as R12) or chlorodifluoromethane (known in the art as R22) in many applications because environmental concerns over the use of R12 and R22 exist.
  • R32 has been mentioned as a possible replacement for R22 because concern over potential depletion of the ozone layer exists. See Allied Chemical's Product Data Sheet on Genetron ® 32, 1963. Currently, R22 is used in closed loop refrigeration systems and in particular, in commercial food refrigeration systems. Both R32 and R125 have properties similar to those of R22 so that it is possible to substitute R32 or R125 for R22 with minimal changes in equipment being required.
  • R32 is immiscible with mineral oil as shown in Comparative A below and R125 is immiscible with mineral oil as shown in Comparative E below. Also, blends of R32 and R125 are immiscible with mineral oil as shown in Comparative G below.
  • Alkyl benzene lubricants are immiscible in R32 as shown in Comparatives B through D below and are not useful therewith. Also, alkyl benzene lubricants are immiscible with blends of R32 and R125 as shown in Comparative F below.
  • lubricants may be soluble in R32, or R125 over a wide range of temperatures, but as the concentration of the lubricant increases, the temperature range over which complete miscibility occurs, i.e., only one liquid phase is present, narrows substantially.
  • two consolute temperatures i.e., a lower and a higher temperature, may exist. That is, a relatively low temperature below which two distinct liquid phases are present and above which the two phases become miscible and a higher temperature at which the single phase disappears and two phases appear again may exist.
  • a diagram of such a system for R502 refrigerant is shown as FIG. 2 in the Kruse et al. paper mentioned above.
  • U.S. Patent 4,971,712 teaches that monofunctional polyoxyalkylene glycols having 50% ethylene oxide and 50% propylene oxide, such as 50HB400 (registered trademark) from Union Carbide, are miscible with R134a.
  • 50HB400 registered trademark
  • Japanese 2,283,797 published November 21, 1990 teaches compositions of pentafluoroethane and monofunctional polyoxyalkylene glycols.
  • the monofunctional polyoxyalkylene glycol 50HB400 (registered trademark) which is a copolymer of ethylene oxide and propylene oxide and has a butyl group on one end thereof is miscible with R134a.
  • the monofunctional polyoxyalkylene glycol 50HB400 (registered trademark) which is a copolymer of ethylene oxide and propylene oxide and has a butyl group on one end thereof is immiscible with R32.
  • the monofunctional polyoxyalkylene glycol which is polypropylene oxide having a butyl group on one end thereof is miscible with R134a.
  • the monofunctional polyoxyalkylene glycol which is polypropylene oxide having a butyl group on one end thereof is immiscible with R32.
  • the miscible lubricant is selected from the group consisting of polyoxyalkylene glycol which is at least difunctional with respect to the hydroxyl groups; polyoxyalkylene glycol having a fluorinated alkyl group on at least one end thereof; fluorinated silicone having units therein selected from the group consisting of fluoroalkyl and alkyl wherein if both units are present, at least 25% of the siloxane units have a fluoroalkyl substituent thereon; and mixtures thereof.
  • the present invention provides a composition for use in refrigeration and air-conditioning comprising: (a) hydrofluorocarbon refrigerant selected from the group consisting of difluoromethane, pentafluoroethane, and mixtures thereof and (b) a sufficient amount to provide lubrication of at least one lubricant selected from the group consisting of: (i) polyoxyalkylene glycol which is at least difunctional with respect to the hydroxyl groups, (ii) polyoxyalkylene glycol having a cap of a fluorinated alkyl group on at least one end thereof, (iii) fluorinated silicone having units therein selected from the group consisting of fluoroalkyl and alkyl wherein if both units are present, at least 25% of the siloxane units have a fluoroalkyl substituent thereon; and mixtures thereof.
  • the lubricant has a molecular weight of about 300 to about 6,000, a viscosity of about 5 to about 300 centistokes at 37°C, and is miscible in combination with the hydrofluorocarbon refrigerant in the range between about 25°C and at least about 30°C.
  • the present invention also provides a method for improving lubrication in refrigeration and air- conditioning equipment using hydrofluorocarbon refrigerant selected from the group consisting of difluoromethane, pentafluoroethane, and mixtures thereof.
  • the method comprises the step of: employing a lubricant selected from the group consisting of polyoxyalkylene glycol which is at least difunctional with respect to the hydroxyl groups, polyoxyalkylene glycol having a cap of a fluorinated alkyl group on at least one end thereof, fluorinated silicone having units therein selected from the group consisting of fluoroalkyl and alkyl wherein if both units are present, at least 25% of the units have a fluoroalkyl substituent thereon; and mixtures thereof.
  • the lubricant has a molecular weight of about 300 to about 6,000 and has a viscosity of about 5 to about 300 centistokes.
  • the lubricant is miscible in combination with the fluorine-containing refrigerant in the range between about 25°C and at least about 30°C.
  • hydrofluorocarbon refrigerant of the present invention is selected from those listed in Table I below.
  • R32 may also be blended with R134a.
  • R125 may also be blended with 1,1,1- trifluoroethane (known in the art as HFC-143a) .
  • R22 is used in very large quantities in air- conditioning and commercial food refrigeration systems Since we have found that R32 and R125 differ in being much less miscible than R134a with lubricants, substitution for R22 becomes more difficult. Lubricants
  • the condensation of hot refrigerant gases in the condensing heat exchanger can be affected if the exchanger is coated with lubricant preferentially so that condensation of the refrigerant occurs by contact with the lubricant film. Thereafter, the two-phase must pass through a pressure reduction to the low temperature stage where the refrigerant evaporates and absorbs the heat given up in cooling air and condensing moisture. If lubricant separates at the condenser, then the performance of the evaporator stage can be affected if separate phases persist as the two-phase mixture passes through the pressure reduction step. As with the condenser, accumulation of lubricant on the evaporator coils can affect heat exchange efficiency.
  • U.S. Patent 4,755,316 teaches a lubricant of at least one polyoxyalkylene glycol which is at least difunctional with respect to hydroxyl groups, has a molecular weight between about 300 and about 2,000, has a viscosity of about 15 to about 150 centistokes at 37°C, and has a viscosity index of at least 20.
  • the polyoxyalkylene glycols preferably have at least 80 percent propylene oxide units; the remaining units may be ethylene oxide, butylene oxide, or other units such as esters and olefins which may be polymerized with propylene oxide.
  • Patent 4,900,463 teaches a lubricant which is a single phase blend of (i) at least one polyoxyalkylene glycol which has a molecular weight between about 300 and about 2000, a viscosity of about 10 to about 157 centistokes at 37°C, and a viscosity index of at least 20 and (ii) chlorotrifluoroethylene oil having a viscosity of about 0.8 to about 1000 centistokes at 25°C.
  • polyoxyalkylene glycol refers to compounds produced by addition polymerization of alkylene oxides, initiated by a molecule having one or more active hydrogens. Commonly, these compounds have terminal hydroxyl groups.
  • the compound may be a copolymer of two or more alkylene oxides and the copolymer may be random or block copolymer. Examples of initiators include water, alcohols, polyalcohols, glycols, and amines.
  • the weight percentage of oxyalkylene groups in the chain is at least 80% and the remaining 20% may be other units including but not limited to polyester, polyamide, and polyvinyl chloride units.
  • the polyoxyalkylene glycol has the formula
  • R 1 -[(R 2 0) n R 3 ] m wherein R x is a residue of a compound having 1 to 8 hydroxyl groups or a hydroxyl group, R 2 is an alkylene moiety having 2 to 4 carbon atoms, R 3 is hydrogen or an alkyl group with 1 to 10 carbon atoms, and n and m are numbers such that the molecular weight of the polyoxyalkylene glycol is 300 to 3,000.
  • polyoxyalkylene glycols are commercially available.
  • the polyoxyalkylene glycols may be random or block polymers or copolymers of ethylene oxide, propylene oxide, butylene oxide, or other alkylene oxides. Most preferably, the polyoxyalkylene glycols are random or block copolymers of ethylene oxide and propylene oxide or a polymer of propylene oxide. Blends of polyoxyalkylene glycols having different molecular weights may also be used in the present invention.
  • Chlorotrifluoroethylene oils having viscosities from about 0.8 to about 1000 centistokes at 25°C are available commercially.
  • Preferred chlorotrifluoroethylene oils have a viscosity of about 100 to about 1,000 centistokes at 25°C.
  • the weight ratio of polyoxyalkylene glycol used to chlorotrifluoroethylene oil used is about 99:1 to about 1:99. More preferably, the weight ratio is about 10:90 to about 56:44.
  • glycols have a molecular weight between about 300 and about 3,000, a viscosity of about 5 to about 150 centistokes at 37°C, and a viscosity index of at least 20.
  • the foregoing fluorinated lubricants comprise the formula (I)
  • R,OR 2 [AO] m (BO) n R 4 wherein m is 4 to 36, n is 0 to 36, R 2 is -CH(CH 3 )CH 2 - or a direct bond, R ! and R 4 are independently selected from the group consisting of hydrogen, alkyl group, and fluorinated alkyl group, Rj can also be a residue of a compound having 1 to 8 active hydrogens, and A and B are the same or different and selected from the group consisting of methyl, ethyl, propyl, or butyl. At least one of R 1 and R 4 is a fluorinated alkyl group. Examples of alkyl groups include methyl, ethyl, propyl, and butyl.
  • the lubricant may be terminated by a hydrogen at one end and a fluorinated alkyl group at the other end, by an alkyl group at one end and a fluorinated alkyl group at the other end, or by a fluorinated alkyl group at both ends.
  • the fluorinated alkyl group may be branched or straight chain as long as fluorine atoms are attached thereto.
  • the foregoing fluorinated lubricants may be formed by fluorinating polyoxyalkylene glycols.
  • the polyoxyalkylene glycols used may have primary carbons at both ends, a primary carbon at one end and a secondary carbon at the other end, or secondary carbons at both ends.
  • the polyoxyalkylene glycols used have a primary carbon at one end and a secondary carbon at the other end or secondary carbons at both ends.
  • At least one of Rj and R ⁇ is a fluorinated alkyl group of the formula
  • x is 1 to 4 and y is 0 to 15. More preferably, x is 1 and y is 0 so that at least one of Rj and R 4 is a fluorinated alkyl group of the formula -CH 2 CF 3 or x is 1 and y is 2 so that at least one of R x and R 4 is a fluorinated alkyl group of the formula -CH 2 (CF 2 ) 2 CF 3 . Even more preferably, both R t and are fluorinated alkyl groups, m is 7 to 34, and n is 0.
  • the foregoing fluorinated lubricating compositions may be formed by capping a polyoxyalkylene glycol with at least one fluorinated alkyl group.
  • the lubricating compositions may be formed by copolymerizing ethylene and propylene oxides and terminating the resulting copolymer with at least one fluorinated alkyl group.
  • the foregoing fluorinated lubricants wherein one end has an alkyl group and the other end has a fluorinated alkyl group or both ends have fluorinated alkyl groups are formed as follows.
  • the polyoxyalkylene glycol is converted to the tosylate by treatment with p-toluenesulfonyl chloride in a suitable base such as pyridine and then the tosylated polyglycol is reacted with the sodium alkoxide of the appropriate fluorinated alcohol.
  • the foregoing fluorinated lubricants wherein one end has a hydroxyl group and the other has a fluorinated alkyl group are formed as follows.
  • An a * lcohol initiator such as the sodium alkoxide of trifluoroethanol is used in the polymerization of polypropylene oxide.
  • the fluorinated lubricant is a fluorinated copolymer of butylene oxide and propylene oxide or is a mixture of fluorinated butylene oxide and fluorinated propylene oxide.
  • a mixture of any of the above three classes of lubricants may also be used.
  • lubricants are fluorinated silicones having units 14 therein selected from the group consisting of fluoroalkyl and alkyl; if both fluoroalkyl and alkyl units are present, at least 25% of the siloxane units have a fluoroalkyl substituent thereon.
  • the 5 fluorinated silicone has a molecular weight between about 280 and about 6,000 and a viscosity of about 10 to about 300 centistokes at 38°C (0.1 to 3.0cm 2 /sec) .
  • the fluorinated silicone is of the 10 formula
  • R 3 Si[OSi (R 2 ) (CI ⁇ CHA) ] m [OSi (R 2 ) (R 2 ) ] ⁇ 0Si (R 3 ) 3
  • R t is a partially or fully fluorinated alkyl group having 1 to 3 carbon atoms
  • each of R 2 is the same or different and is hydrogen, methyl, ethyl, or 15 propyl
  • each of R 3 is the same or different and is a methyl, ethyl, vinyl, phenyl, or CH 2 CH 2 R wherein R is a partially or fully fluorinated alkyl group having l to 3 carbon atoms
  • m is about 2 to 40
  • n is about 0 to about 40.
  • a fluorinated silicone which may be useful is disclosed in U.S. Patent 3,642,626.
  • the silicone has the following formula
  • the silicone has a viscosity of 50 to 100 centistokes (0.5 to 1 cm 2 /sec) .
  • the fluorinated silicone is of the formula 30 (CH 3 ) 3 Si [OSi (CH 3 ) (CK j CH j CFa) ] m [OSi (CH 3 ) (CH 3 ) ] n 0Si (CH 3 ) 3 wherein m is about 2 to about 40 and n is 0 to about 40.
  • n is equal 35 to 0 and m is 2 to 40 so that the fluorinated silicone is of the formula
  • n is not equal to 0, at least 50% of the units are methyltrifluoropropyl.
  • the fluorinated silicones may be formed by any known method such as those disclosed in U.S. Patents 2,961,425 and 4,818,423.
  • the range of miscibility is not the only factor to be considered when one is selecting a lubricant for air conditioning service or other refrigeration application. Lubricating properties also must be satisfactory for the intended application. Practically, this means that for these applications, the viscosity of the lubricant will be about 10-150 centistokes, preferably about 32 centistokes (CS) at 37°C. with a viscosity index of at least 20 in order that the lubricant is sufficiently viscous at high temperatures to lubricate while remaining sufficiently fluid to circulate around the refrigeration circuit at low temperatures. The range of viscosity may also be expressed as about 2-24 centistokes at 98.9°C. In addition, the lubricant should be chemically stable and not cause corrosion or other problems in long-term service. Other factors which should be considered in selecting lubricant are compatibility, lubricity, safety, and the like.
  • Stabilizers may also be added to the present refrigeration compositions.
  • the stabilizers of commonly assigned U.S. Patents 4,755,316; 4,900,463; and 4,975,212 may be used herein.
  • the stabilizer comprises: (i) at least one component selected from the group consisting of phenol and trivalent phosphorus compounds and (ii) at least one epoxide selected from the group consisting of aromatic epoxide and fluorinated alkyl epoxide.
  • the phenol is phenol selected from the group consisting of:
  • 4,4-biphenyldiols and derivatives thereof hydroquinone; t-butyl hydroquinone; and other derivatives of hydroquinone.
  • the most preferred phenols are hydroquinone and 2,6-di-tert-4-methylphenol.
  • the foregoing phenols are commercially available.
  • mixtures of phenols may be used in addition to the use of a single phenol in the present invention.
  • phenol as used herein includes sterically hindered phenols.
  • the trivalent phosphorus compound is trivalent phosphorus compound selected from the group consisting of tris(4-nonylphenyl)phosphite; tris(2,4-di-tert-butylphenyl)phosphite;
  • the preferred trivalent phosphorus compound is tris(2,4-di-tert-butylphenyl)phosphite.
  • the foregoing phosphorus compounds are commercially available. As mentioned earlier, mixtures of phosphorus compounds may be used in addition to the use of a single phosphorus in the present invention.
  • Preferred aromatic epoxides are of the formula
  • R 2 is OCH 2 CHCH 2 -0;
  • Rj is hydrogen, alkyl having 1 to 20 carbon atoms, fluoroalkyl having 1 to 20 carbon atoms, aryl having 6 to 28 carbon atoms, or fluoroaryl having 1 to 28 carbon atoms;
  • M is aryl selected from the group consisting of phenyl, naphthyl, anthracyl, and phenanthrenyl, or alkylaryl; and each n and m is from 1 to 10.
  • the aromatic epoxide is arorr__ic epoxide selected from the group consisting of butylphenylglycidyl ether; pentylphenylglycidyl ether; hexylphenylglycidyl ether; heptylphenylglycidyl ether; octylphenylglycidyl ether; nonylphenylglycidyl ether; glycidyl methyl phenyl ether; decylphenylglycidyl ether; 1,4-diglycidyl phenyl ether and derivatives thereof; 1,4-diglycidyl naphthyl ether and derivatives thereof; 2,2' [[ [5- heptadecafluorooctyl]1,3phenylene]bis[[2,2,2trifluorome thyl]ethylidene]oxymethylene]bisoxirane and derivatives thereof;
  • aromatic epoxide is naphthyl glycidyl ether.
  • aromatic epoxides are commercially available.
  • mixtures of aromatic epoxides may be used in addition to the use of a single aromatic epoxide in the present invention.
  • Preferred fluorinated alkyl epoxides are of the formula wherein R is fluorinated or perfluorinated alkyl group having 1 to 20 carbon atoms. More preferably, the fluorinated alkyl epoxide is fluorinated alkyl epoxide selected from the group consisting of glycidyl trifluoromethyl ether; glycidyl pentafluoroethyl ether; glycidyl heptafluoropropyl ether; and glycidyl monofluorobutyl ether.
  • the most preferred fluorinated alkyl epoxide is glycidyl pentafluoroethyl ether.
  • the foregoing fluorinated alkyl epoxides are commercially available.
  • mixtures of fluorinated alkyl epoxides may be used in addition to the use of a single fluorinated alkyl epoxide.
  • the ratio of phenol or phosphorus to epoxide in the stabilizing polyoxyalkylene glycols can be varied from 1:99 to 99:1.
  • the amount of phenol and aromatic or fluorinated alkyl epoxide used is about 0.01 to about 5 percent by weight based on the amount of the polyoxyalkylene glycols.
  • C-A stands for Comparative A
  • C-B stands for Comparative B
  • C-C stands for Comparative C
  • C-D stands for Comparative D
  • C-E stands for Comparative E
  • C-F stands for Comparative F
  • C- G stands for Comparative G.
  • Ref refrigerant
  • Lub stands for lubricant. The viscosity was taken at 37°C and is expressed in centistokes. MW means molecular weight. Immis means immiscible.
  • Emery 2930A (registered trademark) is a short chain fatty acid ester of trimethylolpropane available from Emery.
  • Emery 2917 (registered trademark) is neopentyl dipelargonate available from Emery.
  • C-H stands for Comparative H
  • C-I stands for Comparative I
  • C-J stands for Comparative J
  • C-K Comparative K
  • Ref refrigerant
  • Lub stands for lubricant.
  • the viscosity was taken at 37°C and is expressed in centistokes.
  • MW means molecular weight. Misc means miscible.
  • Immis means immiscible.
  • Comparative N and C-0 stands for Comparative 0.
  • Ref stands for refrigerant and Lub stands for lubricant.
  • the viscosity was taken at 37°C and is expressed in centistokes.
  • MW means molecular weight.
  • Misc means miscible.
  • Immis means immiscible.
  • R32, R125, and blends of R125 and R143a show good miscibility with polyoxyalkylene glycols having a fluorinated alkyl group on one end thereof.
  • P425 is difunctional polypropylene oxide available from Dow Chemical.
  • Lub B is bis(trifluoroethyl ether) of polypropylene glycol.
  • Lub C is dimethyl/methyltrifluoropropyl siloxane with 50% methyltrifluoropropyl units.
  • FS 1265 (registered trademark) is methyltrifluoropropyl siloxane available from Dow-Corning.
  • E-l stands for Example 1
  • E-2 stands for Example 2
  • E-3 stands for Example 3
  • E-4 stands for Example 4
  • E-5 stands for Example 5
  • E-6 stands for Example 6
  • E-7 stands for Example 7
  • E-8 stands for Example 8
  • E-9 stands for Example 9
  • E-1 ' 0 stands for Example 10
  • E-ll stands for Example 11
  • E-12 stands for Example 12.
  • the weight percent ratio of R32 to R125 is 75:25.
  • the weight percent ratio of R125 to R143a is 50:50.
  • Ref stands for refrigerant and Lub stands for lubricant.
  • the viscosity was taken at 37°C and is expressed in centistokes.
  • MW means molecular weight. Immis means immiscible.

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Abstract

L'invention concerne une composition destinée à être utilisée en réfrigération et en climatisation. La composition comprend: (a) un réfrigérant hydrofluorocarbure choisi dans le groupe constitué par le difluorométhane, le pentafluoroéthane ainsi que des mélanges de ceux-ci; et (b) une quantité suffisante assurant une lubrification d'au moins un lubrifiant choisi dans le groupe constitué par: (i) le polyoxyalkylène glycol, lequel est au moins difonctionnel par rapport aux groupes hydroxyles, (ii) le polyoxyalkylène glycol ayant une coiffe d'un groupe alkyle fluoré sur au moins une de ses extrémités, (iii) du silicone fluoré dans lequel se trouvent des unités choisies dans le groupe constitué par le fluoroalkyle et l'alkyle dans lequel si les deux unités sont présentes, au moins 25 % des unités de siloxane portent un substituant fluoroalkyle, ainsi que des mélanges de ceux-ci. Le lubrifiant a une masse moléculaire comprise entre environ 300 et environ 6.000, une viscosité comprise entre environ 5 et environ 300 centistokes à 37 °C, et il est miscible en combinaison avec le réfrigérant (a) dans une plage comprise entre environ 25 °C et au moins environ 30 °C.
PCT/US1992/002401 1991-04-19 1992-03-25 Compositions de refrigeration contenant un refrigerant hydrofluorocarbure et un lubrifiant WO1992018580A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0536940A2 (fr) * 1991-10-11 1993-04-14 Imperial Chemical Industries Plc Composition de fluide de travail
WO1994009096A1 (fr) * 1992-10-09 1994-04-28 Imperial Chemical Industries Plc Composition de fluide energetique
EP0675331A2 (fr) * 1994-03-30 1995-10-04 Kabushiki Kaisha Toshiba Système de conditionnement d'air avec un échangeur de chaleur intermédiaire intégré dans lequel deux sortes différentes de réfrigérants sont mises en circulation

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US4755316A (en) * 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
US4944890A (en) * 1989-05-23 1990-07-31 E. I. Du Pont De Nemours And Company Compositions and process of using in refrigeration
EP0386851A2 (fr) * 1989-03-09 1990-09-12 Shell Internationale Researchmaatschappij B.V. Lubrifiants de réfrigération
EP0400894A1 (fr) * 1989-06-02 1990-12-05 Union Carbide Chemicals And Plastics Company, Inc. Compositions de réfrigération et procédé d'utilisation
EP0402009A1 (fr) * 1989-06-02 1990-12-12 Union Carbide Chemicals And Plastics Company, Inc. Compositions pour réfrigération par compression et méthode pour les utiliser
WO1991009921A1 (fr) * 1989-12-21 1991-07-11 Allied-Signal Inc. Lubrifiants de refrigeration a base de silicone partiellement fluoree

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US4755316A (en) * 1987-10-23 1988-07-05 Allied-Signal Inc. Refrigeration lubricants
EP0386851A2 (fr) * 1989-03-09 1990-09-12 Shell Internationale Researchmaatschappij B.V. Lubrifiants de réfrigération
US4944890A (en) * 1989-05-23 1990-07-31 E. I. Du Pont De Nemours And Company Compositions and process of using in refrigeration
EP0400894A1 (fr) * 1989-06-02 1990-12-05 Union Carbide Chemicals And Plastics Company, Inc. Compositions de réfrigération et procédé d'utilisation
EP0402009A1 (fr) * 1989-06-02 1990-12-12 Union Carbide Chemicals And Plastics Company, Inc. Compositions pour réfrigération par compression et méthode pour les utiliser
WO1991009921A1 (fr) * 1989-12-21 1991-07-11 Allied-Signal Inc. Lubrifiants de refrigeration a base de silicone partiellement fluoree

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0536940A2 (fr) * 1991-10-11 1993-04-14 Imperial Chemical Industries Plc Composition de fluide de travail
EP0536940A3 (en) * 1991-10-11 1993-11-03 Ici Plc Lubricants
WO1994009096A1 (fr) * 1992-10-09 1994-04-28 Imperial Chemical Industries Plc Composition de fluide energetique
EP0675331A2 (fr) * 1994-03-30 1995-10-04 Kabushiki Kaisha Toshiba Système de conditionnement d'air avec un échangeur de chaleur intermédiaire intégré dans lequel deux sortes différentes de réfrigérants sont mises en circulation
EP0675331A3 (fr) * 1994-03-30 1997-11-12 Kabushiki Kaisha Toshiba Système de conditionnement d'air avec un échangeur de chaleur intermédiaire intégré dans lequel deux sortes différentes de réfrigérants sont mises en circulation
US5784893A (en) * 1994-03-30 1998-07-28 Kabushiki Kaisha Toshiba Air conditioning system with built-in intermediate heat exchanger with two different types of refrigerants circulated

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