EP0781316A4 - IMPROVED HYDROCARBON LUBRICANTS FOR USE WITH IMMISIBLE COOLANTS - Google Patents

IMPROVED HYDROCARBON LUBRICANTS FOR USE WITH IMMISIBLE COOLANTS

Info

Publication number
EP0781316A4
EP0781316A4 EP95931605A EP95931605A EP0781316A4 EP 0781316 A4 EP0781316 A4 EP 0781316A4 EP 95931605 A EP95931605 A EP 95931605A EP 95931605 A EP95931605 A EP 95931605A EP 0781316 A4 EP0781316 A4 EP 0781316A4
Authority
EP
European Patent Office
Prior art keywords
composition
lubricant
refrigerant
oil
hydrocarbon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP95931605A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0781316A1 (en
Inventor
Jose L Reyes-Gavilan
Alan D Eckard
Thomas G Flak
Todd R Tritcak
Leonard Aconsky
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Witco Corp
Original Assignee
Witco Corp
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 Corp filed Critical Witco Corp
Publication of EP0781316A1 publication Critical patent/EP0781316A1/en
Publication of EP0781316A4 publication Critical patent/EP0781316A4/en
Withdrawn legal-status Critical Current

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    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • 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
    • 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
    • C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
    • C10M101/02—Petroleum fractions
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/06—Well-defined hydrocarbons aromatic
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C—CHEMISTRY; METALLURGY
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/08—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least 2 hydroxy groups
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    • C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
    • C10M131/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen and halogen only
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    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/10—Alcohols; Ethers; Aldehydes; Ketones
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    • C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
    • C10M131/12—Acids; Salts or esters thereof
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    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • 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
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    • 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
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/06—Well-defined aromatic compounds
    • C10M2203/065—Well-defined aromatic compounds used as base material
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
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    • C10M2219/046—Overbasedsulfonic acid salts
    • 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
    • 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
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M2223/043—Ammonium 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.
  • 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)
EP95931605A 1994-09-07 1995-08-28 IMPROVED HYDROCARBON LUBRICANTS FOR USE WITH IMMISIBLE COOLANTS Withdrawn EP0781316A4 (en)

Applications Claiming Priority (5)

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
US301694 1994-09-07
US42650095A 1995-04-20 1995-04-20
US426500 1995-04-20
PCT/US1995/010888 WO1996007721A1 (en) 1994-09-07 1995-08-28 Enhanced hydrocarbon lubricants for use with immiscible refrigerants

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EP0781316A1 EP0781316A1 (en) 1997-07-02
EP0781316A4 true EP0781316A4 (en) 1999-07-14

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GB9901667D0 (en) * 1999-01-26 1999-03-17 Ici Plc Lubricant composition
EP1167495B1 (en) * 1999-03-05 2010-04-21 Idemitsu Kosan Co., Ltd. Refrigerating machine oil compositions
JP4316044B2 (ja) * 1999-04-01 2009-08-19 出光興産株式会社 冷凍機油組成物
JP2001181660A (ja) * 1999-12-28 2001-07-03 Daikin Ind Ltd 作動流体および冷凍装置
US6516837B2 (en) 2000-09-27 2003-02-11 Honeywell International Inc. Method of introducing refrigerants into refrigeration systems
US6736991B1 (en) * 2003-02-12 2004-05-18 Crompton Corporation Refrigeration lubricant for hydrofluorocarbon refrigerants
US8796193B2 (en) 2003-08-01 2014-08-05 Nippon Oil Corporation Refrigerating machine oil compositions
US8506839B2 (en) * 2005-12-14 2013-08-13 E I Du Pont De Nemours And Company Absorption cycle utilizing ionic liquids and water as working fluids
US8980808B2 (en) 2011-08-03 2015-03-17 Cognis Ip Management Gmbh Lubricant compositions with improved oxidation stability and service life
KR102315318B1 (ko) * 2017-01-13 2021-10-22 허니웰 인터내셔날 인코포레이티드 냉각제, 열 전달 조성물, 방법 및 시스템
CN111303427B (zh) * 2020-05-14 2020-09-04 富海(东营)新材料科技有限公司 高纯度低灰分聚砜类树脂的工业化提纯工艺

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CA2199008A1 (en) 1996-03-14
BR9508899A (pt) 1997-11-25
CN1159205A (zh) 1997-09-10
WO1996007721A1 (en) 1996-03-14
CN1053006C (zh) 2000-05-31
AU692923B2 (en) 1998-06-18
HUT76913A (hu) 1998-01-28
JPH10505623A (ja) 1998-06-02
KR970705626A (ko) 1997-10-09
NO971040L (no) 1997-05-06
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MX9701644A (es) 1998-02-28
AU3496795A (en) 1996-03-27

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