EP0643753A4 - Lubrifiants a base d'ester de polyol pour compresseurs a grand rendement. - Google Patents

Lubrifiants a base d'ester de polyol pour compresseurs a grand rendement.

Info

Publication number
EP0643753A4
EP0643753A4 EP93914086A EP93914086A EP0643753A4 EP 0643753 A4 EP0643753 A4 EP 0643753A4 EP 93914086 A EP93914086 A EP 93914086A EP 93914086 A EP93914086 A EP 93914086A EP 0643753 A4 EP0643753 A4 EP 0643753A4
Authority
EP
European Patent Office
Prior art keywords
acyl groups
mixture
group
consisting essentially
balance
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Withdrawn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
EP93914086A
Other languages
German (de)
English (en)
Other versions
EP0643753A1 (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/fr
Application filed by Henkel Corp filed Critical Henkel Corp
Publication of EP0643753A1 publication Critical patent/EP0643753A1/fr
Publication of EP0643753A4 publication Critical patent/EP0643753A4/fr
Withdrawn legal-status Critical Current

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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
    • 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
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • 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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    • 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
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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
    • C—CHEMISTRY; METALLURGY
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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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    • 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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    • C10M2203/06—Well-defined aromatic compounds
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    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/026—Butene
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    • C10M2219/108—Phenothiazine
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    • C10M2223/061—Metal salts
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    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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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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    • C10N2040/42—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 and/or wear resistance, corrosion inhibition, and the like along with the lubricant base stocks which contribute the primary lubricity to the compounded lubricants; refriger ⁇ ant working fluids including 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 organic refrigerating heat transfer flu ⁇ ids such as pentafluoroethane, 1,1-difluoroethane, 1,1,1- trifluroethane, and tetrafluoroethanes, most particularly 1,1,1,2-tetrafluoroethane.
  • the lubricants and base stocks, in combination with these heat transfer fluids are particularly suitable for lubricating compressors that require ISO grades from about 320 to about 1000 because of their heavy duty cycles.
  • 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 trans ⁇ fer fluids such as trichlorofluoro ethane and dichlorodi- fluoromethane.
  • chlorofluorocarbon heat trans ⁇ fer fluids such as trichlorofluoro ethane and dichlorodi- fluoromethane.
  • 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, commonly known in the art as "Refrigerant 134a" or simply "R134a”.
  • Other fluoro-substituted ethanes are also desirable working flu ⁇ ids.
  • Esters of hindered polyols which are defined for this purpose as organic molecules containing at least five carbon atoms, at least 2 -OH groups, and no hydrogen atoms directly bonded to any carbon atom that is directly bonded to a carbon atom bearing an -OH group, have already been recognized in the art as high quality lubricant basestocks for almost any type of refrigeration machinery employing a fluorocarbon refrigerant, particularly one free from chlorine.
  • ester mixtures according to this invention should have a viscosity of not more than 1300, more preferably not more than 1100, still more preferably not more than 990, centistokes at 40° C.
  • ester mixtures according to this invention should have a viscosity of at least 300, or with increasing preference in the order given, at least 450, 600, or 810, centistokes at 40° C.
  • esters or mixtures of esters made by reacting (i) a mixture of alcohol molecules se ⁇ lected from the group consisting of 2,2-dimethylol-l-buta- nol (also known as “trimethylolpropane” and often abbrevi- ated hereinafter as “TMP”) ; di-trimethylolpropane (often abbreviated hereinafter as "DTMP”) , a molecule with four hydroxyl groups and one ether linkage, formally derived from two molecules of TMP by removing one hydroxyl group from one of the TMP molecules and one hydrogen atom from a hydroxyl group of the other TMP molecule to form water and join the two remainders of the original TMP molecules with an ether bond; 2,2-dimethylol-l,3-propanediol (also known as "pentaerythritol” and often abbre
  • acyl groups are counted as a single group, irrespective of the number of valences they have. For example, each mole- cule of adipic acid yields a single, dibasic, acyl group when completely esterified.
  • esters or mixture of esters by reacting acid de ⁇ rivatives 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.
  • acid de ⁇ rivatives 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 understood that the es ⁇ ters defined herein by reaction with acids can be equally well obtained by reaction of alcohols with the correspond ⁇ ing 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.
  • a total of at least 60, 75, 85, 90, 95, or 98 % of the hydroxyl groups in the mixture of alcohols that could be reacted to make the mixture of esters according to this invention are PE, DPE, and/or TPE molecules, and independ ⁇ ently, with increasing preference in the order given, at least 60, 75, 85, 90, 95, or 98 % of the hydroxyl groups in the mixture of alcohols that could be reacted to make esters according to this invention are PE molecules.
  • At least 60, 75, 85, 90, 95, or 98 % of the monobasic acid molecules in the acid mixture consist of molecules having no more than ten carbon atoms each and, with increasing preference in the order given, at least 60, 75, 85, 90, 95, or 98 % of the dibasic acid molecules in the acid mix ⁇ ture consist of molecules having no more than ten carbon atoms each, or more preferably from five to seven carbon atoms each.
  • a total of at least 60, 75, 85, 90, 95, or 98 % of the monobasic acid molecules in the acid mixture consist of molecules having either five or nine carbon atoms each.
  • These preferences for the acyl groups and alcohol moi ⁇ eties in esters according to this invention are based on empirically determined generalizations. In order to achieve the desired range of viscosity, it is advantageous to have a substantial fraction of dibasic acids and of al ⁇ cohols with at least four hydroxyl groups.
  • PE is less expensive than DTMP and is free from the ether linkage in DTMP, which increases the hygroscop- icity of the esters formed and thereby may promote unde ⁇ sirable corrosion of the metal surfaces lubricated.
  • 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.
  • 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.
  • 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 dispersant ⁇ , 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 alkylammonium carboxylates; hetero- cyclic nitrogen containing compounds, e.g., thiadiazoles, substituted i idazolines, and oxazolines; quinolines, qui- nones, and anthraquinones; propyl gallate; barium dinonyl naphthalene s,
  • 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 in ⁇ clude 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 char- aeteristics 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 turbid ⁇ ity, 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 re- mains single phase up to +30° C, although it is increas ⁇ ingly more preferable if the single phase behavior is maintained up to 40, 56, 71, 88, or 100 ° C.
  • 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 od- 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
  • 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 (" in") , 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.
  • a suitable ester mixture as described above was pre ⁇ pared by reacting a mixture of alcohol molecules in which 99.9 % were PE molecules, with most of the remainder being DPE molecules, with a mixture of acid molecules that in- eluded 80 % of 3-methylfc.utanoic acid and 19 % of adipic acid, with the remainder predominantly other five carbon monobasic acids.
  • This ester mixture had a viscosity at 40° C of about 900 centistokes.

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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)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Lubricants (AREA)

Abstract

Lubrifiant de haute qualité pour service sévère, destiné au refroidissement des compresseurs, notamment de ceux qui utilisent des liquides de refroidissement constitués par un hydrofluorocarbone exempt de chlore. Ce lubrifiant est obtenu par mélange d'esters de polyols inhibés, de préférence un penta-érythritol avec un mélange d'acides carboxyliques renfermant au moins une certaine quantité d'acide iso-pentanoïque et au moins 13 % d'acides dibasiques, tels qu'un acide adipique.
EP93914086A 1992-06-03 1993-05-27 Lubrifiants a base d'ester de polyol pour compresseurs a grand rendement. Withdrawn EP0643753A4 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CA002137252A CA2137252A1 (fr) 1992-06-03 1992-06-03 Lubrifiants d'ester polyolique pour des fluides refigerants caloporteurs
PCT/US1992/004438 WO1993024585A1 (fr) 1992-06-03 1992-06-03 Lubrifiants aux esters de polyols pour fluides caloporteurs refrigerants
WOPCT/US92/04438 1992-06-03
US2885693A 1993-03-10 1993-03-10
US28856 1993-03-10
PCT/US1993/004885 WO1993025628A2 (fr) 1992-06-03 1993-05-27 Lubrifiants a base d'ester de polyol pour compresseurs a grand rendement

Publications (2)

Publication Number Publication Date
EP0643753A1 EP0643753A1 (fr) 1995-03-22
EP0643753A4 true EP0643753A4 (fr) 1996-11-06

Family

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Application Number Title Priority Date Filing Date
EP93914086A Withdrawn EP0643753A4 (fr) 1992-06-03 1993-05-27 Lubrifiants a base d'ester de polyol pour compresseurs a grand rendement.

Country Status (4)

Country Link
EP (1) EP0643753A4 (fr)
JP (1) JPH08505159A (fr)
CA (1) CA2137257A1 (fr)
WO (1) WO1993025628A2 (fr)

Families Citing this family (4)

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Publication number Priority date Publication date Assignee Title
KR100348014B1 (ko) * 1994-05-23 2002-11-29 헨켈 코포레이션 하이드로플루오로카본냉매와함께사용하기위한에스테르윤활제의전기저항을증가시키는방법
SG75080A1 (en) * 1994-11-29 2000-09-19 Sanyo Electric Co Refrigerating apparatus and lubricating oil composition
BR0213159A (pt) * 2001-10-10 2004-09-14 Exxonmobil Res & Eng Co Composição de óleo lubrificante biodegradável, e, composição lubrificante
DE102006027602A1 (de) * 2006-06-13 2007-12-20 Cognis Ip Management Gmbh Schmierstoffzusammensetzungen enthaltend Komplexester

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US3523084A (en) * 1966-06-16 1970-08-04 Sinclair Research Inc Lubricating oil ester base composition containing liquid esters of neoalkyl polyols and neoalkyl fatty acids
US3441600A (en) * 1966-06-16 1969-04-29 Sinclair Research Inc Liquid esters of neoalkyl polyols and neoalkyl fatty acids
FR2051665A1 (fr) * 1969-07-10 1971-04-09 Ethyl Corp
US4451144A (en) * 1982-09-27 1984-05-29 Photomatrix Corporation Automatic loader for microfiche duplicators
KR950005694B1 (ko) * 1989-07-05 1995-05-29 가부시끼가이샤 교오세끼 세이힝기주쓰 겡뀨쇼 냉각윤활제
EP0430657A1 (fr) * 1989-11-29 1991-06-05 Asahi Denka Kogyo Kabushiki Kaisha Lubrifiant pour réfrigérateurs
DK0435253T3 (da) * 1989-12-28 1994-06-20 Nippon Oil Co Ltd Køleolier til brug sammen med hydrogenholdige halogencarbonkølemidler
JPH03217494A (ja) * 1990-01-22 1991-09-25 Kao Corp 冷凍機油
EP0786510A1 (fr) * 1990-01-31 1997-07-30 Exxon Chemical Patents Inc. Esters utilisés comme lubrifiants pour réfrigérant à base d'alcane halogéné
JPH03275799A (ja) * 1990-03-23 1991-12-06 Asahi Denka Kogyo Kk 冷凍機油組成物
AU640019B2 (en) * 1990-05-22 1993-08-12 Unichema Chemie Bv Lubricants
US5021179A (en) * 1990-07-12 1991-06-04 Henkel Corporation Lubrication for refrigerant heat transfer fluids
ATE152473T1 (de) * 1991-02-19 1997-05-15 Dea Mineraloel Ag Schmiermittel für kältemaschinen

Non-Patent Citations (2)

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Title
No further relevant documents disclosed *
See also references of WO9325628A3 *

Also Published As

Publication number Publication date
EP0643753A1 (fr) 1995-03-22
WO1993025628A3 (fr) 1995-10-12
WO1993025628A2 (fr) 1993-12-23
CA2137257A1 (fr) 1993-12-23
JPH08505159A (ja) 1996-06-04

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