WO1996007721A1 - Lubrifiants ameliores a hydrocarbures utilises avec des refrigerants non miscibles - Google Patents

Lubrifiants ameliores a hydrocarbures utilises avec des refrigerants non miscibles Download PDF

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Publication number
WO1996007721A1
WO1996007721A1 PCT/US1995/010888 US9510888W WO9607721A1 WO 1996007721 A1 WO1996007721 A1 WO 1996007721A1 US 9510888 W US9510888 W US 9510888W WO 9607721 A1 WO9607721 A1 WO 9607721A1
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WO
WIPO (PCT)
Prior art keywords
composition
lubricant
refrigerant
oil
hydrocarbon
Prior art date
Application number
PCT/US1995/010888
Other languages
English (en)
Inventor
Jose L. Reyes-Gavilan
Alan D. Eckard
G. Thomas Flak
Todd R. Tritcak
Leonard Aconsky
Original Assignee
Witco Corporation
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
Priority claimed from US08/301,694 external-priority patent/US5792383A/en
Application filed by Witco Corporation filed Critical Witco Corporation
Priority to EP95931605A priority Critical patent/EP0781316A4/fr
Priority to AU34967/95A priority patent/AU692923B2/en
Priority to KR1019970701486A priority patent/KR970705626A/ko
Priority to BR9508899A priority patent/BR9508899A/pt
Priority to JP8509544A priority patent/JPH10505623A/ja
Priority to MX9701644A priority patent/MX9701644A/es
Priority to NZ292709A priority patent/NZ292709A/en
Publication of WO1996007721A1 publication Critical patent/WO1996007721A1/fr
Priority to FI970954A priority patent/FI970954A/fi
Priority to NO971040A priority patent/NO971040L/no

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    • 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
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
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    • 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
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    • C10M101/02Petroleum fractions
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02Well-defined hydrocarbons
    • C10M105/06Well-defined hydrocarbons aromatic
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    • C10M105/00Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32Esters
    • C10M105/38Esters of polyhydroxy compounds
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    • C10M107/00Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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    • C10M129/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04Hydroxy compounds
    • C10M129/06Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M131/08Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/10Alcohols; Ethers; Aldehydes; Ketones
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    • C10M131/08Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12Acids; Salts or esters thereof
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    • C10M169/00Lubricating 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
    • C10M169/04Mixtures of base-materials and additives
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    • 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
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    • 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
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    • C10M2203/06Well-defined aromatic compounds
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    • C10M2219/08Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/085Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • 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
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • 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
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • 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
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/043Ammonium or amine salts thereof

Definitions

  • This application is a continuation-in-part of application Serial No. 08/426,500 filed April 20, 1995 and application Serial No. 08/301,694 filed September 7, 1994.
  • This invention relates to fluid refrigeration compositions comprising a hydrocarbon lubricant, such as mineral oil, a refrigerant immiscible with the hydrocarbon lubricant, and additive capable of reducing the interfacial tension between the hydrocarbon lubricant and the immiscible refrigerant.
  • this invention comprises a fluid refrigeration composition
  • a fluid refrigeration composition comprising a hydrocarbon lubricant, such as mineral oil, a fluorohydrocarbon refrigerant immiscible with the hydrocarbon lubricant and a surfactant capable of reducing the interfacial tension between the hydrocarbon lubricant and fluorohydrocarbon refrigerant.
  • CFCs chlorofluorocarbons
  • CFC-115 (1-chloro-l,1,2,2,2- pentafluoroethane)
  • CFC-113 1,1,2-trichloro-l,2,2- trifluoroethane
  • HCFC hydrochlorofluorocarbon
  • HFC hydrofluorocarbon
  • R-22 hydrochlorodifluoromethane
  • R-123 (1,l-dichloro-2,2,2- trifluoroethane
  • R-124 l-chloro-l,2,2,2-tetrafluoro- ethane
  • HCFCs have much lower ozone depletion potentials than do CFCs because even though there is chlorine present in these molecules, they contain hydrogen atoms that cause their decomposition to take place at lower levels of the atmosphere.
  • HFCs examples include R-134a (1,1,1,2- tetrafluoroethane) , R-152a (1,l-difluoroethane) , R-32
  • HFC refrigerants may have desirable physical properties that make them appropriate long term refrigerant alternates, they lack miscibility with naphthenic mineral oils traditionally used as refrigeration compressor lubricants.
  • the mineral oils' chemical stability and miscibility with CFC and HCFC refrigerants, chemical compatibility with all system components, low floe and pour points, high dielectric strength, and proper viscosity provide the properties that enhance their overall performance once charged into the system.
  • the use of naphthenic refrigeration oils in refrigeration or air conditioning applications where HFCs are employed as refrigerants has been considered by some to be inappropriate due to the immiscibility of both fluids.
  • immiscibility or poor dispersibility between the refrigerant and lubricant at unit operating temperatures may provide unsuitable oil return to the compressor. This causes improper heat transfer due to oil coating of the inner surface of the heat exchange coils, and in extreme cases, lubricant starvation of the compressor.
  • the former causes energy efficiency losses, and the latter results in unit burn ⁇ out.
  • Reyes-Gavilan has shown that by using low viscosity naphthenic mineral oil (70 SUS at 37.8 ⁇ C) in the same type of units as those tested by Sanvordenker, the dependence of oil return on unit configuration is eradicated.
  • the agents responsible for oil return in household refrigeration systems aside from low viscosity mineral oils with good flow characteristics in the system and proper lubrication performance in the compressors, are high refrigerant velocities and short return lines between the evaporator and compressor. It is conceivable that those refrigeration or air conditioning systems with either low refrigerant velocities and/or long return lines between the evaporator and the compressor can experience poor oil return, resulting in any of the aforementioned system performance problems.
  • U.S. Patent No. 5,114,605 to Mitsui Petrochemical discloses a composition comprising a hydrofluorocarbon, polyether carbonate and either a mineral oil or alpha olefin oligomer.
  • the general object of this invention is to provide refrigeration fluid compositions comprising a hydrocarbon lubricant, preferably a mineral oil lubricant, and a refrigerant immiscible with the hydrocarbon lubricant containing at least one carbon and one fluorine atom.
  • a more specific object of this invention is to provide refrigeration fluid compositions comprising a mineral oil lubricant and a hydrofluorocarbon refrigerant immiscible with mineral oil.
  • refrigeration fluid compositions comprising a hydrocarbon lubricant, a refrigerant immiscible with the hydrocarbon lubricant containing at least one carbon atom and one fluorine atom, and an effective amount of an additive capable of reducing the interfacial tension between the hydrocarbon lubricant and the immiscible refrigerant.
  • composition of this invention can be used in refrigeration and air conditioning systems with potential oil return difficulties, when charged with straight hydrocarbon oil and HFC refrigerants.
  • the aim is to facilitate oil return to the compressor by making the refrigerant and hydrocarbon lubricant more dispersible with each other, allowing the refrigerant to wash the lubricant off the inner surfaces of the heat exchangers.
  • the invention provides proper lubrication and energy efficiency to the unit, while maintaining adequate chemical and thermal stability within the system.
  • the refrigeration fluid compositions of this invention comprise a hydrocarbon lubricating oil, a refrigerant containing at least one carbon and one fluorine atom and an additive capable of reducing the interfacial tension between the hydrocarbon lubricant and the refrigerant.
  • Suitable hydrocarbon lubricants useful in this invention include paraffinic mineral oils, naphthenic mineral oils, alkylbenzene oils, polyalphaolefins and their oligomers, and mixtures thereof. Minor amounts (1 to 20% by wt.) alkylbenzene with major amounts (99 to 80% by wt.) naphthenic mineral oil are particularly useful for improving the solubility or dispersibility of some additives (i.e. surfactants such as 2,4,7,9-tetramethyl-5- decyne-4,7-diol) in the hydrocarbon oil.
  • Suitable refrigerants useful in this invention include those which contain at least one carbon atom and one fluorine atom.
  • refrigerants examples include R-22 (chlorodifluoromethane) , R-124 (1-chloro- 1,2 , 2,2-tetrafluoroethane) , R-134a (1,1,1,2- tetrafluoroethane) , R-143a (1,l,1-trifluoroethane) , R-152a (1,1-difluoroethane) , R-32 (difluoromethane) , R-125 (1,1,1,2,2-pentafluoroethane) , and mixtures thereof such as R-404a [R-125 (44 wt. %) , R-143a (52 Wt.
  • mixtures can also contain propane as a component of the blend in those applications where the heat exchange fluid is going to be used as an interim retrofit fluid for existing refrigeration and air conditioning equipment.
  • suitable refrigerants can be used with CFC refrigerants, particularly, where residual amounts of these refrigerants are present in a system being retrofitted.
  • the additives useful in this invention for reducing the interfacial tension between lubricant and refrigerant have the property of facilitating the displacement of oil from metal surfaces by the refrigerant. This property can be determined by sealing a refrigerant immiscible at room temperature, such as R134a, with the hydrocarbon lubricant, the hydrocarbon lubricant and additive agents in a glass tube containing a steel or iron chip. A two phase system forms with the lubricating oil constituting the top layer and the refrigerant the bottom layer. The metal chip is then raised up to the oil level in the tube using a magnet and the oil is allowed to completely wet the metal surface by moving the metal chip rapidly up and down in the oil.
  • the additive is suitable for use in this invention, if the refrigerant displaces the oil when the chip is slowly lowered into the liquid refrigerant layer.
  • Suitable additives include surfactants, such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol sold as Surfynol SE, fluorocarbon esters sold as FC-430, anionic fluorohydrocarbon phosphites, phosphates, carboxylates (salts and acids), sulfonates, etc. such as F(CF 2 CF 2 ) 3t08 ⁇ CH j -CH j SCH j CH j CO j Li sold as Zonyl FSA, mixture of o n
  • hydrocarbon lubricants made up of two or more components.
  • minor amounts of alkylbenzene hydrocarbons improve the solubility or dispersibility of some additives in mineral oil. While applicants do not wish to be bound by any theory, applicants believe that the interfacial tension at the refrigerant (liquid) /1GS interface is reduced to the point where the spreading coefficient (S) refrigerant liquid on steel is slightly positive or very close to zero which enables the refrigerant to displace the oil with slight agitation or due to the difference in specific gravity.
  • S is the spreading coefficient of fluid (1) against fluid (2) on the surface of a third phase, (3) a solid.
  • Y the respective interfacial tensions.
  • Y 12 is a significant positive number as is apparent from the prominent meniscus between the two phases. Also, since the oil preferentially wets and continues to wet the steel even with some degree of agitation;
  • the additive or surface active agent can be used in the range of 0.001 to 5 parts by weight per 100 parts by weight lubricating oil. Concentrates can be prepared containing up to 100 parts by weight surface active agent per 100 parts by weight lubricating oil for purposes of adding same to refrigerating systems containing hydrocarbon lubricating oils containing no surface active agent or insufficient amounts for the desired purpose.
  • the weight ratio of lubricating oil to immiscible refrigerant can range from 0.10 to 15 parts by weight per 100 parts by weight refrigerant as is conventional in this art.
  • the weight ratio of polyol ester to hydrocarbon lubricant can range from about 1:99 to 1:3, preferably 1:19 to 1:4. Accordingly, we believe it is advantageous to retrofit hydrocarbon lubricant CFC systems to employ HFCs by adding concentrate compositions containing polyol ester and surfactant such as 2,4,7,9-tetramethyl-5-decyne-4,7- diol or fluorinated ester directly to the compressor system with or without additional hydrocarbon lubricant provided the surface active agent in the compressor system constitutes at least 0.001 parts by weight per 100 parts by weight of the lubricating fluids in the compressor.
  • the polyol ester/surfactant concentrate can comprise from about .1 to 100 parts by weight surfactant per 100 parts by weight polyol ester.
  • Suitable polyol esters comprise polyhydric alcohol esters of aliphatic monocarboxylic acids containing 4 to 25 carbon atoms alone or together with di or tricarboxylic acids.
  • Suitable polyhydric alcohols can contain from 2 to 6 hydroxy groups, such as neopentyl alcohol, 1,1,1-trimethylol ethane, 1,1,1-trimethylol propane, pentaerythritol, etc.
  • Suitable aliphatic carboxylic acids include branched and unbranched acids such as butyric acid, isobutyric acid, 2-ethylhexanoic acid, n-octanoic acid, valeric acid, isopentanoic acid, hexanoic acid, heptanoic acid, nonanoic acid, stearic acid, etc.
  • Dicarboxylic acids such as maleic acid, succinic acid, adipic acid etc. and tricarboxylic acids such as trimellitic acid can be used in small amounts to adjust the viscosity of the polyol ester.
  • Table I presents suitable stability and wear enhancing additives that may be used with hydrocarbon lubricants employing surface active agents in refrigeration and air conditioning applications with lubricant immiscible refrigerants.
  • Example I A 9 mL glass tube was charged with 0.050 mL of 70 SUS naphthenic mineral oil (Suniso IGS) containing 0.5% by weight candidate surfactant, a 6mm steel chip and 0.70 ml 1,1,1,2-tetrafluoroethane (R-134a) and sealed. A two phase system was formed with the naphthenic mineral oil constituting the top layer and the hydrofluorocarbon the bottom layer. The metal chip was completely wetted with oil by moving the chip rapidly up and down in the oil phase using a magnet. The chip was then slowly lowered into the tetrafluoroethane layer. The results are set forth below in Table II. TABLE II
  • PIB Diisoamyl
  • Tetra is (2-ethylhexanol) Oil clings to chip and glass. Pentaerytnritol
  • FC-430 Oil removed from chip and glass by R-134a Two layers very dispersible.
  • Example II A 9 ml glass tube was charged with 0.050 ml of 70 SUS naphthenic mineral oil (Suniso IGS) containing
  • Example III A multizone pump down solenoid medium temperature supermarket freezer rack in New England, equipped with two five door freezer rack cabinets (each 105.6 ft 3 ), a compressor (Copelametic Model No. R-76 WMT3T) located approximately 6 to 7 ft. off the ground, and evaporators on the floor of each cabinet was retrofitted. The refrigerant gas and oil travel through approximately 20 ft. of 7/8 inch diameter vertical and horizontal suction return lines before arriving at the compressor through a 1 3/8 inch tube. The system was charged with R-402A (30 pound charge) , which comprised 38 wt. % R125 (pentafluoroethane) , 60 wt.
  • R-402A (30 pound charge) , which comprised 38 wt. % R125 (pentafluoroethane) , 60 wt.
  • the oil was drained from the system leaving some residual alkylbenzene; charged with 150 SUS oil comprising primarily naphthenic mineral oil, 10 wt. % alkylbenzene, and 0.05 wt. % Surfynol SE; evacuated for 1/2 hour and allowed to run for 1 hour to flush residual alkylbenzene oil from the system. During this time, the oil pressure switch did not go off and -17°F and -10°F temperature were attained for the respective racks. After 1 hour, the oil was drained again from the system and replaced with fresh 150 SUS oil comprising primarily naphthenic mineral oil, 10 wt. % alkylbenzene, and 0.05 wt. % Surfynol SE.
  • Example IV The compositions listed below in Table III have been tested with R-134a and 2,4,7,9-tetramethyl-5-decyne- 4,7-diol surfactants with encouraging results.
  • H-l stands for a 12cSt naphthenic mineral oil at 40°C
  • H-2 stands for a 38cSt white naphthenic mineral oil at 40°C
  • H-3 stands for a 29 to 30cSt naphthenic mineral oil at 40°C
  • H-4 stands for an 18cSt naphthenic mineral oil at 40°C
  • H-5 stands for 29 to 30cSt alkylbenzene at 40°C
  • PI stands for a polyester of tri ethylol propane, 70% valeric acid and 30% isovaleric acid
  • P2 stands for a polyester of pentaerythritol and 2-ethylhexanoic acid
  • P3 stands for a polyester of pentaerythritol, valeric acid, isovaleric acid and adipic acid.
  • Example v This example illustrates that anionic fluorohydrocarbons surfactants can be used in this invention.
  • Example II was repeated using an ISO 10 naphthenic mineral oil and the candidate anionic and nonionic fluorohydrocarbon surface active agents listed below in Table IV.
  • Zonyl FSN and Zonyl FSO are F(CF 2 CF 2 ) 3 _ 8 -CH 2 CH 2 0(CH 2 CH 2 0) x H having different levels of oxyethylene units.
  • Table AN stands for anionic and NON stands for nonionic.
  • lubricant compositions comprising mixtures of either 90% by weight mineral oil and 10% by weight polyester or 70% by weight mineral oil and 30% by weight polyester were tested in the manner described in Example II using ISO 10 naphthenic mineral oil and either polyester P-l, which stands for a polyolester of trimethylol propane and 30% valeric acid and P-2, which stands for a polyolester of 2-ethylhexanoic acid, 79% neopentyl glycol and 21% pentaerythritol.
  • polyester P-l which stands for a polyolester of trimethylol propane and 30% valeric acid
  • P-2 which stands for a polyolester of 2-ethylhexanoic acid

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

Abstract

Compositions fluides de réfrigération renfermant un lubrifiant à hydrocarbures, un réfrigérant non miscible et un additif permettant d'atténuer la tension de surface entre le lubrifiant à hydrocarbures et le réfrigérant.
PCT/US1995/010888 1994-09-07 1995-08-28 Lubrifiants ameliores a hydrocarbures utilises avec des refrigerants non miscibles WO1996007721A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP95931605A EP0781316A4 (fr) 1994-09-07 1995-08-28 Lubrifiants ameliores a hydrocarbures utilises avec des refrigerants non miscibles
AU34967/95A AU692923B2 (en) 1994-09-07 1995-08-28 Enhanced hydrocarbon lubricants for use with immiscible refrigerants
KR1019970701486A KR970705626A (ko) 1994-09-07 1995-08-28 불혼화성 냉매와 함께 사용하기 위한 증강된 탄화수소 윤활제(Enhanced hydro carbon lubricants for use with immiscible refrigerants)
BR9508899A BR9508899A (pt) 1994-09-07 1995-08-28 Lubrificantes de hidrocarbonetos aperfeiçoados para uso com refrigerantes imiscíveis
JP8509544A JPH10505623A (ja) 1994-09-07 1995-08-28 不混和冷媒と併用するための強化型炭化水素潤滑剤
MX9701644A MX9701644A (es) 1994-09-07 1995-08-28 Lubricantes de hidrocarburo mejorados para uso con refrigerantes inmiscibles.
NZ292709A NZ292709A (en) 1994-09-07 1995-08-28 Refrigeration fluid containing fluorocarbon lubricant immiscible with the refrigerant, and an additive that reduces interfacial tension
FI970954A FI970954A (fi) 1994-09-07 1997-03-06 Tehostetut hiilivetyvoiteluaineet käytettäviksi sekoittamattomien jäähdytysaineiden kanssa
NO971040A NO971040L (no) 1994-09-07 1997-03-06 Forbedrede hydrokarbonsmöremidler for anvendelse med ikke blandbare kjölemidler

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US08/301,694 US5792383A (en) 1994-09-07 1994-09-07 Reduction of enterfacial tension between hydrocarbon lubricant and immiscible liquid refrigerant
US08/301,694 1994-09-07
US42650095A 1995-04-20 1995-04-20
US08/426,500 1995-04-20

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JP (1) JPH10505623A (fr)
KR (1) KR970705626A (fr)
CN (1) CN1053006C (fr)
AU (1) AU692923B2 (fr)
BR (1) BR9508899A (fr)
CA (1) CA2199008A1 (fr)
FI (1) FI970954A (fr)
HU (1) HU218032B (fr)
MX (1) MX9701644A (fr)
NO (1) NO971040L (fr)
NZ (1) NZ292709A (fr)
PL (1) PL319054A1 (fr)
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WO2000044860A1 (fr) * 1999-01-26 2000-08-03 Imperial Chemical Industries Plc Composition lubrifiante de refrigeration
WO2000053704A1 (fr) * 1999-03-05 2000-09-14 Idemitsu Kosan Co., Ltd. Compositions huileuses pour machines refrigerantes
WO2001048125A1 (fr) * 1999-12-28 2001-07-05 Daikin Industries, Ltd. Fluide hydraulique et appareil de refrigeration
WO2002027248A1 (fr) * 2000-09-27 2002-04-04 Honeywell International Inc. Procede destine a remplacer des refrigerants dans des systemes de refrigeration
WO2004072215A1 (fr) * 2003-02-12 2004-08-26 Crompton Corporation Lubrifiant pour fluides frigorigenes hydrofluorocarbones
US8796193B2 (en) 2003-08-01 2014-08-05 Nippon Oil Corporation Refrigerating machine oil compositions
US9371500B2 (en) 2011-08-03 2016-06-21 Cognis Ip Management Gmbh Lubricant compositions with improved oxidation stability and service life

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WO1999036485A1 (fr) * 1998-01-16 1999-07-22 E.I. Du Pont De Nemours And Company Compositions de fluides frigorigenes halocarbonees contenant des agents polymeres de retour d'huile
US6299792B1 (en) * 1998-01-16 2001-10-09 E. I. Du Pont De Nemours And Company Halogenated hydrocarbon refrigerant compositions containing polymeric oil-return agents
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WO2000044860A1 (fr) * 1999-01-26 2000-08-03 Imperial Chemical Industries Plc Composition lubrifiante de refrigeration
EP1167495A1 (fr) * 1999-03-05 2002-01-02 Idemitsu Kosan Co., Ltd. Compositions huileuses pour machines refrigerantes
WO2000053704A1 (fr) * 1999-03-05 2000-09-14 Idemitsu Kosan Co., Ltd. Compositions huileuses pour machines refrigerantes
US6878677B1 (en) 1999-03-05 2005-04-12 Idemitsu Kosan Co., Ltd. Refrigerating machine oil compositions
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EP1167495A4 (fr) * 1999-03-05 2004-03-10 Idemitsu Kosan Co Compositions huileuses pour machines refrigerantes
WO2001048125A1 (fr) * 1999-12-28 2001-07-05 Daikin Industries, Ltd. Fluide hydraulique et appareil de refrigeration
AU777230B2 (en) * 1999-12-28 2004-10-07 Daikin Industries, Ltd. Hydraulic fluid and refrigerating apparatus
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WO2002027248A1 (fr) * 2000-09-27 2002-04-04 Honeywell International Inc. Procede destine a remplacer des refrigerants dans des systemes de refrigeration
WO2004072215A1 (fr) * 2003-02-12 2004-08-26 Crompton Corporation Lubrifiant pour fluides frigorigenes hydrofluorocarbones
US8796193B2 (en) 2003-08-01 2014-08-05 Nippon Oil Corporation Refrigerating machine oil compositions
US9371500B2 (en) 2011-08-03 2016-06-21 Cognis Ip Management Gmbh Lubricant compositions with improved oxidation stability and service life

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CN1159205A (zh) 1997-09-10
CN1053006C (zh) 2000-05-31
NZ292709A (en) 1999-04-29
EP0781316A4 (fr) 1999-07-14
JPH10505623A (ja) 1998-06-02
NO971040L (no) 1997-05-06
FI970954A (fi) 1997-05-06
CA2199008A1 (fr) 1996-03-14
HU218032B (hu) 2000-05-28
FI970954A0 (fi) 1997-03-06
AU692923B2 (en) 1998-06-18
PL319054A1 (en) 1997-07-21
BR9508899A (pt) 1997-11-25
HUT76913A (hu) 1998-01-28
AU3496795A (en) 1996-03-27
MX9701644A (es) 1998-02-28
KR970705626A (ko) 1997-10-09
NO971040D0 (no) 1997-03-06
EP0781316A1 (fr) 1997-07-02

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