US3773668A - Lubricating compositions - Google Patents

Lubricating compositions Download PDF

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Publication number
US3773668A
US3773668A US00204329A US3773668DA US3773668A US 3773668 A US3773668 A US 3773668A US 00204329 A US00204329 A US 00204329A US 3773668D A US3773668D A US 3773668DA US 3773668 A US3773668 A US 3773668A
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carbon atoms
oils
ether
percent
esters
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J Denis
G Parc
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IFP Energies Nouvelles IFPEN
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IFP Energies Nouvelles IFPEN
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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
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • 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
    • 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
    • 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
    • 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
    • C10M2203/102—Aliphatic 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
    • 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
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • 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
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/106—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing four carbon atoms only
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/109—Polyethers, i.e. containing di- or higher polyoxyalkylene groups esterified
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/11—Complex polyesters
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/086—Imides
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    • C10M2215/28—Amides; Imides
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    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
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    • C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
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    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/20—Metal working
    • C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
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    • C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
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    • C10N2040/241—Manufacturing joint-less pipes
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    • C10N2040/245—Soft metals, e.g. aluminum
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    • C10N2040/244—Metal working of specific metals
    • C10N2040/246—Iron or steel
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    • C10N2040/244—Metal working of specific metals
    • C10N2040/247—Stainless steel

Definitions

  • ABSTRACT Lubricating compositions particularly useful for manufacturing multigrade oils, hydraulic fluids, oils for industrial gears and cutting oils, comprising 95 percent by weight of a hydrocarbon oil produced according to a conventional process and 5-95 percent by weight of a compound selected from the group consisting of the esters of polyalkyleneglycol ethers complying with the general formula:
  • R is a divalent hydrocarbon radical having from one to 34 carbon atoms
  • R and R are divalent aliphatic radicals having from two to five carbon atoms
  • R and R are monovalent hydrocarbon radicals having from one to twenty-five carbon atoms
  • n and n are integers from two to 50, and those complying with the general formula:
  • R is a hydrocarbon radical of valency m, having from three to carbon atoms, R is a monovalent hydrocarbon radical having from one to carbon atoms, R is a divalent aliphatic radical having from two to five carbon atoms, n is an integer from two to and m is an integer from two to four.
  • This invention relates to new lubricating compositions consisting of mixtures of conventional hydrocarbon oils and derivatives of polyalkyleneglycols.
  • the conventional base oils are prepared according to different methods.
  • the main processes for manufacturing these oils are the acid or solvent refining of vacuum distillates or deasphalted vacuum residues from crude oils, the hydrotreatment of the same petroleum cuts and the oligomerization of olefinic hydrocarbons.
  • a vacuum distillate or deasphalted vacuum residue can be subjected to a solvent extraction for example by means of furfurol or phenol, so as to eliminate from the petroleum cut the aromatic compounds contained therein, then to a series of treatments such as dewaxing, clay bleaching and moderate hydrogenation, at a temperature of from 250 to 350C, under a hydrogen pressure of 20 to 80 kg/cm in the presence of a catalyst.
  • the second process the hydrotreatment of the abovementioned petroleum cuts, may be achieved, for example, according to the teaching of US. Pat. No. 3,560,370, in the name of the applicant.
  • the hydrotreatment is conducted at a temperature of from 350 to 450C, under a hydrogen pressure of from 80 to 240 kg/cm and in the presence of a catalyst.
  • the oil is manufactured by oligomerizing olefinic hydrocarbons having from two to 20 and preferably from nine to 16 carbon atoms per molecule.
  • This oligomerization may be achieved by the action of catalysts consisting of aluminium halides, or by the action of heat, in the presence of organic peroxides acting as initiators.
  • the oils prepared according to the above-described processes generally exhibit viscosity indexes of from 50 to 160 and, more particularly, from 50 to H for solvent refined oils, from 50 to 150 for the hydrorefined oils and from 1 l0 to 160 for the oligomerization oils.
  • oils obtained in the two last above-described processes already exhibit much better characteristics than those obtained by the first process.
  • all these oils require the addition, besides the conventional additives such as detergents or antioxidants, of more or less substantial amounts of viscosity additives, which however, exhibit inherent disadvantages such as poor thermal and/or mechanical stability.
  • the present invention relates to new lubricating compositions which contain generally a compound (A) consisting of a hydrocarbon oil and a compound (B) selected amongst the esters of polyalkyleneglycol ethers.
  • the hydrocarbon oil (A) is selected among the mineral oils obtained either by solvent refining or by acid treatment, or by severe hydrotreatment of vacuum distillates or deasphalted vacuum residues from crude oils and the synthetic oils obtained by oligomerizing olefinic hydrocarbons having from two to 20 carbon atoms per molecule.
  • compound (B) results from the esterification of a dicarboxylic acid by at least one ether of polyalkyleneglycol and of monoalcohol or by the esterifi cation of an ether of polyalkyleneglycol and of polyol by at least one monocarboxylic acid.
  • compound (B) complies with the general formula wherein R is a divalent hydrocarbon radical having from one to 34 carbon atoms, R and R are divalent aliphatic radicals having from two to five carbon atoms, R and R' are monovalent hydrocarbon radicals having from one to 25 carbon atoms, and n and n are integers from two to 50, or with the general formula wherein R is a hydrocarbon radical of valency m,
  • catingcompositions exhibiting viscosity-temperature I characteristics so improved that the amount of viscoshaving from three to 15 carbon atoms, R; is a monovalent hydrocarbon radical having from one to 25 carbon atoms, R is a divalent aliphatic radical having from two to five carbon atoms, n is'an integer from two to 50 and m is an integer from two to four, with the provision that radicals R and R and integer n may be different from one chain to another.
  • Compound (B) may also result from the esterification of an ether of polyalkyleneglycol and of polyol having the formula wherein R R n and m are defined as above, by means of a mixture of monocarboxyli'c acids and dicarboxylic acids HO-C-Rr-C-OH,
  • esters of polyalkeneglycol ethers contemplated according to this invention are miscible with mineral or synthetic oils in rather large proportions, their miscibility with fluid oils being better than with more viscous oils, and better with naphthenic oils than with paraffinic oils.
  • polyethyleneglycol derivatives for a given oil, are less easily miscible than those of polypropyleneglycol, there are used preferably polypropyleneglycol derivatives or still mixed derivatives of poly (ethylene-propylene)glycol in which the ratio ethylene oxide/propylene oxide is kept lower than or equal to l/l.
  • compounds (B) that can be used in the compositions according to the invention, there can be mentioned the dodecanedioate of the ether obtained by condensation of propylene oxide with isobutanol;
  • trioleate of the ether obtained by condensation of a mixture of ethylene and propylene oxides (50/50 by weight) with trimethylolhexane; the tetraheptanoate of the ether obtained by condensation of propylene oxide with pentaerythritol;
  • compositions according to the invention may contain the hydrocarbon oil (A) in a major proportion (50 to 95 percent by weight) as compared withthe ester of polyalkyleneglycol ether (B) (5 to 50 percent by weight), or, on the contrary, the compound (B) may be present in a major proportion (50 to 95 percent by weight) as compared with the compound (A) (5 to 50 percent by weight). More generally, the compositions containing from 5 to percent by weight of each of the compounds (A) and (B) are to be considered.
  • a third solvent such as an ester of dicarboxylic acid or of polyol, e.g., isodecyl adipate, trimethylhexyl azelate, neopentylglycol pelargonate, ethylhexyl sebacate, trimethylolpropane tripelargonate.
  • a third solvent such as an ester of dicarboxylic acid or of polyol, e.g., isodecyl adipate, trimethylhexyl azelate, neopentylglycol pelargonate, ethylhexyl sebacate, trimethylolpropane tripelargonate.
  • compositions of the invention may be used for manufacturing motor oils and particularly multigrade oils; they are also advantageously used for manufacturing hydraulic fluids, oils for gear-boxes, oils for industrial gears or oils for the cut or the forming of metals.
  • the lubricating and anti-wear properties of the compositions according to the invention appear of particular interest since they permit a good working security and an extended life for the mechanisms lubricated therewith.
  • esters of polyalkyleneglycol ethers used in the lubricating compositions of the invention may be prepared by direct esterification of the ether obtained by condensing at least one alkylene oxide with the suitable monoalcohol or polyol, by means of one or more convenient mono or dicarboxylic acids, in the presence of a convenient catalyst, the water produced being removable by azeotropic entrainement by means of a solvent.
  • the remaining acidic products may be removed either by washing with a hydroalcoholic potash solution and then with water or by clay treatment.
  • the solvent is then expelled under vacuum and the residue, consisting of the ester of polyalkyleneglycol ether, may be recovered without having to be distilled.
  • Test of Lubricating Power A lubricating composition consisting of 50 percent by weight of l50'neutral mineral oil and 50 percent by weight of trioleate of the ether obtained by condensation of a 5050 mixture of ethylene oxide and propylene oxide with trimethylolpropane, has been tested for its anti-wear properties and its load capacity.
  • the conditions of the anti-wear test are running speed 1,500 runs per minute,
  • the average diameter of the three lower balls is an indication of the anti-wear power under limit lubrication conditions.
  • R is a divalent aliphatic hydrocarbon radical
  • a third solvent selected from the group consisting of: (a) esters of dicarboxylic acids and aliphatic monoalcohols, and (b) esters of monocarboxylic acids and aliphatic polyolst 4.
  • compound (B) is selected from the group consisting of the esters resulting from the simultaneous esterification of an ether obtained by condensation of propylene oxide with trimethylol propane with a mixture, in a molar ratio of 4/1 of dodecanoic acid and azelaic acid, and the esters resulting from the simultaneous esterifi-

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US00204329A 1970-12-03 1971-12-02 Lubricating compositions Expired - Lifetime US3773668A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7043605A FR2116277A1 (en) 1970-12-03 1970-12-03 Lube oil blends - contg hydrocarbon oil and polyalkylene glycol deriv
FR717113437A FR2133515B2 (de) 1970-12-03 1971-04-15

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JP (1) JPS5339441B1 (de)
BE (1) BE775839A (de)
CA (1) CA982542A (de)
DE (1) DE2159511A1 (de)
ES (1) ES397616A1 (de)
FR (1) FR2133515B2 (de)
GB (1) GB1372375A (de)
IT (1) IT941944B (de)
NL (1) NL7116645A (de)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036771A (en) * 1975-04-16 1977-07-19 Institut Francais Du Petrole Lubricating bases for multigrade oils
US4339236A (en) * 1978-02-21 1982-07-13 Union Carbide Corporation Low foam scouring agents
US4585565A (en) * 1984-11-23 1986-04-29 Aluminum Company Of America Metalworking lubricant comprising mineral oil and alkoxyalkyl ester
US4618441A (en) * 1984-11-23 1986-10-21 Aluminum Company Of America Metalworking with a lubricant composition comprising mineral oil and alkoxyalkyl ester
WO1988005809A1 (en) * 1987-02-06 1988-08-11 Gaf Corporation Propoxylated guerbet alcohols and esters thereof
US4830769A (en) * 1987-02-06 1989-05-16 Gaf Corporation Propoxylated guerbet alcohols and esters thereof
US4928190A (en) * 1984-03-13 1990-05-22 Olympus Optical Co., Ltd. Magnetic recording/reproduction apparatus
US5045586A (en) * 1988-08-04 1991-09-03 Lenick Jr Anthony J O Lubricants for thermoplastic resins
US5185092A (en) * 1990-01-31 1993-02-09 Tonen Corporation Lubricating oil for refrigerator
US5820777A (en) * 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5851968A (en) * 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US5906769A (en) * 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US6544937B2 (en) * 2001-05-22 2003-04-08 Exxonmobile Research And Engineering Company Demulsification of industrial lubricants containing naphthenic basestocks
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems
US20110150163A1 (en) * 2009-12-22 2011-06-23 Westinghouse Electric Company Llc Process for application of lubricant to fuel rod during fuel assembly loading process

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012158503A1 (en) * 2011-05-13 2012-11-22 Tenstech Inc. Esters of structurally symmetric alkoxylated polyols and lubricating compositions comprising the same

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036771A (en) * 1975-04-16 1977-07-19 Institut Francais Du Petrole Lubricating bases for multigrade oils
US4339236A (en) * 1978-02-21 1982-07-13 Union Carbide Corporation Low foam scouring agents
US4928190A (en) * 1984-03-13 1990-05-22 Olympus Optical Co., Ltd. Magnetic recording/reproduction apparatus
US4585565A (en) * 1984-11-23 1986-04-29 Aluminum Company Of America Metalworking lubricant comprising mineral oil and alkoxyalkyl ester
US4618441A (en) * 1984-11-23 1986-10-21 Aluminum Company Of America Metalworking with a lubricant composition comprising mineral oil and alkoxyalkyl ester
WO1988005809A1 (en) * 1987-02-06 1988-08-11 Gaf Corporation Propoxylated guerbet alcohols and esters thereof
US4830769A (en) * 1987-02-06 1989-05-16 Gaf Corporation Propoxylated guerbet alcohols and esters thereof
US5045586A (en) * 1988-08-04 1991-09-03 Lenick Jr Anthony J O Lubricants for thermoplastic resins
US5185092A (en) * 1990-01-31 1993-02-09 Tonen Corporation Lubricating oil for refrigerator
US6296782B1 (en) 1992-06-03 2001-10-02 Henkel Corporation Polyol ester lubricants for refrigerator compressors operating at high temperatures
US6666985B2 (en) 1992-06-03 2003-12-23 Cognis Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US5906769A (en) * 1992-06-03 1999-05-25 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5976399A (en) * 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US6183662B1 (en) 1992-06-03 2001-02-06 Henkel Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US6221272B1 (en) 1992-06-03 2001-04-24 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
US6551524B2 (en) 1992-06-03 2003-04-22 Cognis Corporation Polyol ester lubricants, especially those compatible with mineral oils, for refrigerating compressors operating at high temperatures
US5820777A (en) * 1993-03-10 1998-10-13 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US5851968A (en) * 1994-05-23 1998-12-22 Henkel Corporation Increasing the electrical resistivity of ester lubricants, especially for use with hydrofluorocarbon refrigerants
US6551523B1 (en) 1995-06-07 2003-04-22 Cognis Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
US7018558B2 (en) 1999-06-09 2006-03-28 Cognis Corporation Method of improving performance of refrigerant systems
US6544937B2 (en) * 2001-05-22 2003-04-08 Exxonmobile Research And Engineering Company Demulsification of industrial lubricants containing naphthenic basestocks
US20110150163A1 (en) * 2009-12-22 2011-06-23 Westinghouse Electric Company Llc Process for application of lubricant to fuel rod during fuel assembly loading process
US8599990B2 (en) * 2009-12-22 2013-12-03 Westinghouse Electric Company Llc Process for application of lubricant to fuel rod during fuel assembly loading process

Also Published As

Publication number Publication date
GB1372375A (en) 1974-10-30
CA982542A (en) 1976-01-27
NL7116645A (de) 1972-06-06
JPS5339441B1 (de) 1978-10-21
BE775839A (fr) 1972-05-26
ES397616A1 (es) 1975-03-16
DE2159511A1 (de) 1972-06-08
IT941944B (it) 1973-03-10
FR2133515B2 (de) 1974-07-05
FR2133515A2 (de) 1972-12-01

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