EP0648251A1 - Polyolester als schmiermittel for hocheffiziente kältemaschinen - Google Patents

Polyolester als schmiermittel for hocheffiziente kältemaschinen

Info

Publication number
EP0648251A1
EP0648251A1 EP93914088A EP93914088A EP0648251A1 EP 0648251 A1 EP0648251 A1 EP 0648251A1 EP 93914088 A EP93914088 A EP 93914088A EP 93914088 A EP93914088 A EP 93914088A EP 0648251 A1 EP0648251 A1 EP 0648251A1
Authority
EP
European Patent Office
Prior art keywords
group
balance
weight
lubricant
heat transfer
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Withdrawn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
EP93914088A
Other languages
English (en)
French (fr)
Inventor
Nicholas E. Schnur
Eugene R. Zehler
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.)
Henkel Corp
Original Assignee
Henkel 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 CA002137252A external-priority patent/CA2137252A1/en
Application filed by Henkel Corp filed Critical Henkel Corp
Publication of EP0648251A1 publication Critical patent/EP0648251A1/de
Withdrawn legal-status Critical Current

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    • 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
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/38—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/02—Materials undergoing a change of physical state when used
    • C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
    • C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
    • C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
    • C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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    • 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
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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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    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/10—Groups 5 or 15
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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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    • C10N2040/34—Lubricating-sealants
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    • C10N2040/38—Conveyors or chain belts
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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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    • C10N2040/44—Super vacuum or supercritical use
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    • C10N2040/50—Medical uses

Definitions

  • This invention relates to lubricant base stocks, which can also serve as complete lubricants in some cases; compounded lubricants, which include at least one additive for such purposes as improving high pressure resistance, corrosion inhibition, and the like along with the lubri- cant base stocks which contribute the primary lubricity to the compounded lubricants; refrigerant working fluids in ⁇ cluding lubricants according to the invention along with primary heat transfer fluids, and methods for using these materials.
  • the lubricants and lubricant base stocks are generally suitable for use with most or all halocarbon refrigerants and are particularly suitable for use with substantially chlorine-free, fluoro-group-containing or ⁇ ganic refrigerating heat transfer fluids such as penta- fluoroethane, 1,1-difluoroethane, 1,1,1-trifluroethane, and tetrafluoroethanes, most particularly 1,1,1,2-tetra- fluoroethane.
  • the lubricants and base stocks, in combina ⁇ tion with these heat transfer fluids, are particularly suitable for domestic refrigerators with high operating efficiency, where relatively low viscosity lubricants are needed.
  • Chlorine-free heat transfer fluids are desirable for use in refrigerant systems, because their escape into the atmosphere causes less damage to the environment than the currently most commonly used chlorofluorocarbon heat transfer fluids such as trichlorofluoromethane and di- chlorodifluoromethane.
  • chlorofluorocarbon heat transfer fluids such as trichlorofluoromethane and di- chlorodifluoromethane.
  • the widespread commercial use of chlorine-free refrigerant heat transfer fluids has been hindered, however, by the lack of commercially adequate lubricants. This is particularly true for one of the most desirable working fluids, 1,1,1,2-tetrafluoroethane, com- monly known in the art as "Refrigerant 134a" or simply "R134a".
  • Other fluoro-substituted ethanes are also desir ⁇ able working fluids.
  • Home refrigerators of the normal type generally are required to maintain cool temperatures within a relatively small and well insulated space, and the temperature of their environment, to which waste heat must be discharged, does not normally vary over a wide range, because it usu ⁇ ally is a temperature in which humans can be reasonably comfortable. Therefore, relatively low power compressors are generally employed for such normal home refrigerators, and lubricants with relatively low viscosities at normal human comfort temperatures are generally satisfactory e- chanically. Because the environmental temperature never rises very high, any drastic decrease in viscosity of the lubricant with temperature is largely avoided.
  • low viscosity lubricants are preferred for economy of operation, because with all other factors held equal, a low viscosity lubricant reduces power consumption by the lubricated machinery, and, with the rising cost of electric power, consumers are becoming more sensitive to efficiency in their home appliances.
  • a certain minimum viscosity is required to avoid excessive depletion of the lubricant from those surfaces of the re ⁇ frigerating machinery that need lubrication while running but are not immersed in the refrigerant working fluid, during periods of idleness for the compressor and other mechanically active parts of the refrigeration machinery.
  • esters according to this invention should have a viscosity of not more than 17, or with in ⁇ creasing preference in the order given, not more than 15.0, 14.2, 13.8, 13.0, 12.6, 12.0, 11.7, 11.3, or 11.0, centistokes at 40° C.
  • esters according to this invention should have a viscosity of at least 6.1, or with increasing preference in the order given, at least 6.5, 6.9, 7.3, 7.7, 8.0, 8.3, 8.5, 8.7, or 8.9, centi ⁇ stokes at 40° C
  • esters or mixtures of esters made by reacting (i) a mixture of alcohol molecules in which at least 45 % are molecules of 2,2-dimethylol-l- butanol (also called “trimethylolpropane” and often ab- breviated hereinafter as “TMP”) and at least 75 % of the remainder of the molecules are selected from the group consisting of 2,2-dimethylpropane-l,3-diol (also called “neopentyl glycol” and often abbreviated hereinafter as "NPG”) , 2,2-dimethylol-l-propanol (also called “trimeth- ylol ethane” and often abbreviated hereinafter as "TME”) , and 2,2-dimethylolpropane-l,3-diol (also called “penta- erythritol” and often ab
  • esters or mixture of esters by reacting acid derivatives such as acid anhydrides, acyl chlorides, and esters of the acids with lower molecular weight alcohols than those desired in the ester products according to this invention, instead of reacting the acids themselves.
  • the acids are generally preferred for economy and are normally specified herein, but it is to be under- stood that the esters defined herein by reaction with ac ⁇ ids can be equally well obtained by reaction of alcohols with the corresponding acid derivatives, or even by other reactions.
  • the only critical feature is the mixture of acyl groups and alcohol moieties in the final mixture of esters formed.
  • Per ⁇ centages of specific chemical molecules or moieties speci- fied herein such as the percentages of carboxyl and hy ⁇ droxyl groups stated in the preceding sentence, are to be understood as number percentages, which will be mathemat ⁇ ically identical to percentages by chemical equivalents, with Avogadro's number of each specified chemical moiety regarded as a single chemical equivalent.
  • At least 70, 78, 85, 89, 93, 96, or 98 % of the alcohol mole ⁇ cules reacted to make the ester molecules in the lubri- cants according to this invention are TMP.
  • At least 74, 78, 82, 85, 92, 97, or 99 % of the acid molecules reacted to make the esters according to this invention are selected from acids containing five carbon atoms per molecule, and inde- pendently, with increasing preference in the order given, at least 72, 76, 81, 85, 90, 93, 95, or 97 % of the total of the five carbon acid molecules in this acid component consist of pentanoic acid (straight chain) .
  • Branched acids give esters with a lower viscosity index, but with usually higher absolute viscosities at normal ambient human com ⁇ fort temperatures or any lower temperature, than un- branched acids with the same number of carbon atoms.
  • Al ⁇ cohols with two hydroxyl groups yield esters with lower viscosities than those with three hydroxyl groups, while alcohols with four or more hydroxyl groups yield esters of still higher viscosity.
  • Acids with six or more carbon at- oms yield esters with more viscosity than those with fewer carbon atoms, and acids with four or, especially, fewer than four, carbon atoms are substantially more easily hy- drolyzed during use than those with higher numbers of car ⁇ bon atoms; such hydrolysis is disadvantageous, because the acid produced by hydrolysis promotes damaging corrosion of at least some of the types of metal surfaces normally be ⁇ ing lubricated. Also, the corrosiveness of a carboxylic acid to most metals found in refrigerator compressors in ⁇ creases as the number of carbon atoms in the acid molecule decreases.
  • molecules of the ester of TMP with pentanoic acid have proved close to ideal for low viscosity lubrication, because they are as low in viscosity as is ever normally desirable for exist ⁇ ing refrigerating machinery, are miscible in all propor ⁇ tions with most or all fluorocarbon refrigerants over a temperature range of at least -55° C up to at least the boiling point of the fluorocarbon refrigerant at normal atmospheric pressure and often to still higher tempera ⁇ tures which can easily be reached in the compression stage of a refrigerator, are capable of solubilizing other high- er viscosity and less soluble hindered polyol esters, and are substantially less likely than esters of acids with fewer than five carbon atoms per molecule to promote cor ⁇ rosion.
  • composition of the mixture of acids that actually re ⁇ acted can be determined by analysis of the product ester mixture for its acyl group content.
  • the acid(s) reacted will be lower boiling than the alcohol(s) reacted and the product ester(s) .
  • the product is often ready for use as a lubricant or lubricant base stock ac ⁇ cording to this invention.
  • the content of free acid in the prod ⁇ uct after the first vacuum distillation may be further reduced by treatment with epoxy esters as taught in U. S.
  • Patent 3,485,754 or by neutralization with any suitable alkaline material such as lime, alkali metal hydroxide, or alkali metal carbonates. If treatment with epoxy esters is used, excess epoxy ester may be removed by a second distillation under very low pressure, while the products of reaction between the epoxy ester and residual acid may be left behind in the product without harm. If neutrali ⁇ zation with alkali is used as the refinement method, sub ⁇ sequent washing with water, to remove any unreacted excess alkali and the small amount of soap formed from the excess fatty acid neutralized by the alkali, is strongly pre ⁇ ferred before using the product as a lubricant and/or base stock according to this invention.
  • any suitable alkaline material such as lime, alkali metal hydroxide, or alkali metal carbonates.
  • ester(s) as de- scribed herein will function satisfactorily as complete lubricants. It is generally preferable, however, for a complete lubricant to contain other materials generally denoted in the art as additives, such as oxidation resist ⁇ ance and thermal stability improvers, corrosion inhibi- tors, metal deactivators, lubricity additives, viscosity index improvers, pour and/or floe point depressants, de ⁇ tergents, dispersants, antifoaming agents, anti-wear agents, and extreme pressure resistant additives. Many additives are multifunctional.
  • certain ad ⁇ ditives may impart both anti-wear and extreme pressure resistance properties, or function both as a metal de- activator and a corrosion inhibitor.
  • all additives preferably do not exceed 8 % by weight, or more preferably do not exceed 5 % by weight, of the total com ⁇ pounded lubricant formulation.
  • An effective amount of the foregoing additive types is generally in the range from 0.01 to 5 % for the anti- oxidant component, 0.01 to 5 % for the corrosion inhibitor component, from 0.001 to 0.5 % for the metal deactivator component, from 0.5 to 5 % for the lubricity additives, from 0.01 to 2 % for each of the viscosity index improvers and pour and/or floe point depressants, from 0.1 to 5 % for each of the detergents and dispersants, from 0.001 to 0.1 % for anti-foam agents, and from 0.1 - 2 % for each of the anti-wear and extreme pressure resistance components. All these percentages are by weight and are based on the total lubricant composition.
  • Suitable oxidation resistance and thermal stability improvers are diphenyl-, dinaphthyl-, and phenyl- naphthyl-amines, in which the phenyl and naphthyl groups can be substituted, e.g., N,N'-diphenyl phenylenediamine, p-octyldiphenylamine, p,p-dioctyldiphenylamine, N-phenyl- 1-naphthyl amine, N-pheny1-2-naphthyl amine, N-(p-dodecyl)- pheny1-2-naphthyl amine, di-1-naphthylamine, and di-2- naphthylamine; phenothazines such as N-alkylphenothia- zines; imino(bisbenzyl) ; and hindered phenols such as 6- (t-butyl) phenol, 2,
  • cuprous metal deactivators examples include imidazole, benzamidazole, 2-mercaptobenzthiazole, 2,5-di- mercaptothiadiazole, salicylidine-propylenediamine, pyr- azole, benzotriazole, tolutriazole, 2-methylbenzamidazole, 3,5-dimethyl pyrazole, and methylene bis-benzotriazole. Benzotriazole derivatives are preferred.
  • more general metal deactivators and/or corrosion inhib ⁇ itors include organic acids and their esters, metal salts, and anhydrides, e.g., N-oleyl-sarcosine, sorbitan monoole- ate, lead naphthenate, dodecenyl-succinic acid and its par ⁇ tial esters and amides, and 4-nonylphenoxy acetic acid; primary, secondary, and tertiary aliphatic and cycloali- phatic amines and amine salts of organic and inorganic ac- ids, e.g., oil-soluble alkylam onium carboxylates; hetero- cyclic nitrogen containing compounds, e.g., thiadiazoles, substituted imidazolines, and oxazolines; quinolines, qui- nones, and anthraquinones; propyl gallate; barium dinonyl naphthalene sulfon
  • Suitable lubricity additives include long chain derivatives of fatty acids and natural oils, such as esters, amines, amides, imidazolines, and borates.
  • suitable viscosity index improvers in ⁇ clude polymethacrylates, copolymers of vinyl pyrrolidone and methacrylates, polybutenes, and styrene-acrylate co ⁇ polymers.
  • suitable pour point and/or floe point de ⁇ pressants include polymethacrylates such as methacrylate- ethylene-vinyl acetate terpolymers; alkylated naphthalene derivatives; and products of Friedel-Crafts catalyzed con ⁇ densation of urea with naphthalene or phenols.
  • detergents and/or dispersants examples include polybutenylsuccinic acid amides; polybutenyl phos- phonic acid derivatives; long chain alkyl substituted aro- matic sulfonic acids and their salts; and metal salts of alkyl sulfides, of alkyl phenols, and of condensation prod ⁇ ucts of alkyl phenols and aldehydes.
  • Suitable anti-foam agents include sili- cone polymers and some acrylates.
  • Suitable anti-wear and extreme pressure resistance agents include sulfurized fatty acids and fatty acid esters, such as sulfurized octyl tallate; sulfurized terpenes; sulfurized olefins; organopolysulfides; organo phosphorus derivatives including amine phosphates, alkyl acid phosphates, dialkyl phosphates, aminedithiophos- phates, trialkyl and triaryl phosphorothionates , trialkyl and triaryl phosphines, and dialkylphosphites, e.g., amine salts of phosphoric acid monohexyl ester, amine salts of dinonylnaphthalene sulfonate, triphenyl phosphate, tri- naphthyl phosphate, diphenyl cresyl and dicresyl phenyl phosphates, naphthyl diphenyl phosphate, triphenylphos-
  • the lubricant base stocks and lubricants be substantially free of such poly- ether polyols.
  • substantially free it is meant that the compositions contain no more than about 10 % by weight, preferably no more than about 2.6 % by weight, and more preferably no more than about 1.2 % by weight of the materials noted.
  • One major embodiment of the present invention is a refrigerant working fluid comprising both a suitable heat transfer fluid such as a fluorocarbon and a lubricant ac- cording to this invention.
  • the refrigerant working fluid and the lubricant should have chemical characteristics and be present in such a proportion to each other that the working fluid remains homogeneous, i.e., free from visually detectable phase separations or turbidity, over the entire range of working temperatures to which the working fluid is exposed during operation of a refrigeration system in which the working fluid is used. This working range may vary from -60° C to as much as +175° C.
  • the working fluid remains single phase up to +30° C, although it is increasingly more preferable if the single phase behavior is maintained up to 40, 56, 71, 88, or 100 ⁇ C. Similar ⁇ ly, it is often adequate if the working fluid compositions remains a single phase when chilled to 0° C, although it is increasingly more preferable if the single phase behav ⁇ ior persists to -10, -20, -30, -40, or -55 ⁇ C.
  • Single phase mixtures with chlorine free hydrofluorocarbon re ⁇ frigerant working fluids are usually obtained with the suitable and preferred types of esters described above.
  • the lubricant composition forms a single phase in all proportions with the heat transfer fluid over the temper ⁇ ature ranges noted above. This however, is a very strin ⁇ gent requirement, and it is often sufficient if there is single phase behavior over the entire temperature range for a working fluid mixture containing up to 1 % by weight of lubricant according to this invention. Single phase behavior over a temperature range for mixtures containing up to 2, 4, 10, and 15 % by weight of lubricant is suc ⁇ cessively more preferable.
  • miscible is used in the refrigeration lubrica ⁇ tion art and hereinafter, except when part of the phrase “miscible in all proportions", when two phases are formed but are readily capable of being mixed into a uniform dis ⁇ persion that remains stable as long as it is at least mod ⁇ erately agitated mechanically.
  • Some refrigeration (and other) compressors are designed to operate satisfactorily with such miscible mixtures of refrigerant working fluid and lubricant.
  • mixtures that lead to coagu ⁇ lation or significant thickening and form two or more phases are unacceptable commercially and are designated herein as "immiscible”. Any such mixture described below is a comparative example and not an embodiment of the present invention.
  • Another major embodiment of the invention is the use of a lubricant according to the invention, either as total lubricant or lubricant base stock, in a process of operat- ing refrigerating machinery in such a manner that the lub ⁇ ricant is in contact with the refrigerant working fluid.
  • the alcohol(s) and acid(s) to be reacted, together with a suitable catalyst such as dibutyltin diacetate, tin oxalate, phosphoric acid, and/or tetrabutyl titanate, were charged into a round bottomed flask equipped with a stir- rer, thermometer, nitrogen sparging means, condenser, and a recycle trap. Acid(s) were charged in about a 15 % mol ⁇ ar excess over the alcohol(s). The amount of catalyst was from 0.02 to 0.1 % by weight of the weight of the total acid(s) and alcohol(s) reacted.
  • the reaction mixture was heated to a temperature be ⁇ tween about 220 and 230° C, and water from the resulting reaction was collected in the trap while refluxing acids were returned to the reaction mixture. Partial vacuum was maintained above the reaction mixture as necessary to achieve a reflux rate of between 8 and 12 % of the orig ⁇ inal reaction mixture volume per hour.
  • the reaction mixture was sampled occasionally for de- termination of hydroxyl number, and after the hydroxyl num ⁇ ber had fallen below 5.0 mg of KOH per gram of mixture, the majority of the excess acid was removed by distilla ⁇ tion after applying the highest vacuum obtainable with the apparatus used, corresponding to a residual pressure of about 0.05 torr, while maintaining the reaction temper ⁇ ature.
  • the reaction mixture was then cooled, and any re ⁇ sidual acidity was removed, if desired, by treatment with lime, sodium hydroxide, or epoxy esters.
  • the resulting lubricant or lubricant base stock was dried and filtered before phase compatibility testing.
  • ml One milliliter (“ml”) of the lubricant to be tested is placed into a thermal shock resistant, volumetrically graduated glass test tube 17 millimeters ("mm") in diam ⁇ eter and 145 mm long.
  • the test tube is then stoppered and placed into a cooling bath regulated to -29 ⁇ 0.2° C. Af ⁇ ter the tube and contents have equilibrated in the cooling bath for 5 minutes ("min") , sufficient refrigerant working fluid is added to give a total volume of 10 ml.
  • the tube contents are visu- ally examined for evidence of phase separation. If there is any such phase separation, the tube is shaken to deter ⁇ mine whether the combination can be rated as miscible or is totally unacceptable.
  • This lubri- cant base stock had an ISO grade of 10.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
EP93914088A 1992-06-03 1993-05-27 Polyolester als schmiermittel for hocheffiziente kältemaschinen Withdrawn EP0648251A1 (de)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
WOPCT/US92/04438 1992-06-03
CA002137252A CA2137252A1 (en) 1992-06-03 1992-06-03 Polyol ester lubricants for refrigerant heat transfer fluids
PCT/US1992/004438 WO1993024585A1 (en) 1992-06-03 1992-06-03 Polyol ester lubricants for refrigerant heat transfer fluids
US2919693A 1993-03-10 1993-03-10
US29196 1993-03-10
PCT/US1993/004889 WO1993024588A1 (en) 1992-06-03 1993-05-27 Polyol ester lubricants for high efficiency refrigerators

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EP0648251A1 true EP0648251A1 (de) 1995-04-19

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JP (1) JPH07507347A (de)
CA (1) CA2136851A1 (de)
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Publication number Priority date Publication date Assignee Title
DE4333323A1 (de) * 1993-09-30 1995-04-06 Hoechst Ag Gemische isomerer Pentansäuren, aus ihnen hergestellte Ester und deren Verwendung als Schmiermittel
AU699190B2 (en) * 1994-05-23 1998-11-26 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
DE4421784A1 (de) * 1994-06-22 1996-01-04 Henkel Kgaa Streufähiges Teppichreinigungsmittel
US5503761A (en) * 1994-08-02 1996-04-02 Exxon Research & Engineering Co./Hatco Corp. Technical pentaerythritol esters as lubricant base stock
US20040089839A1 (en) * 2002-10-25 2004-05-13 Honeywell International, Inc. Fluorinated alkene refrigerant compositions
CN101229998A (zh) * 2007-12-21 2008-07-30 王伟松 三羟甲基丙烷脂肪酸酯的合成方法

Family Cites Families (4)

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Publication number Priority date Publication date Assignee Title
EP0430657A1 (de) * 1989-11-29 1991-06-05 Asahi Denka Kogyo Kabushiki Kaisha Schmiermittel für Kühlgeräte
EP0435253B1 (de) * 1989-12-28 1994-03-09 Nippon Oil Company, Limited Kühlschranköle zum Gebrauch mit Hydrogen enthaltenden Halogenocarbonkühlmitteln
JPH03275799A (ja) * 1990-03-23 1991-12-06 Asahi Denka Kogyo Kk 冷凍機油組成物
US5021179A (en) * 1990-07-12 1991-06-04 Henkel Corporation Lubrication for refrigerant heat transfer fluids

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Title
See references of WO9324588A1 *

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CA2136851A1 (en) 1993-12-09
JPH07507347A (ja) 1995-08-10
WO1993024588A1 (en) 1993-12-09

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