EP0272575A2 - Esters de polyols neutres ayant une viscosité élevée - Google Patents

Esters de polyols neutres ayant une viscosité élevée Download PDF

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Publication number
EP0272575A2
EP0272575A2 EP87118481A EP87118481A EP0272575A2 EP 0272575 A2 EP0272575 A2 EP 0272575A2 EP 87118481 A EP87118481 A EP 87118481A EP 87118481 A EP87118481 A EP 87118481A EP 0272575 A2 EP0272575 A2 EP 0272575A2
Authority
EP
European Patent Office
Prior art keywords
acids
class
acid
fatty acids
range
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.)
Granted
Application number
EP87118481A
Other languages
German (de)
English (en)
Other versions
EP0272575B2 (fr
EP0272575B1 (fr
EP0272575A3 (en
Inventor
Karl-Heinz Dr. Schmid
Uwe Dr. Ploog
Alfred Dr. Meffert
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.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
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
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0272575A2 publication Critical patent/EP0272575A2/fr
Publication of EP0272575A3 publication Critical patent/EP0272575A3/de
Application granted granted Critical
Publication of EP0272575B1 publication Critical patent/EP0272575B1/fr
Publication of EP0272575B2 publication Critical patent/EP0272575B2/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • C10M105/40—Esters containing free hydroxy or carboxyl groups
    • 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
    • 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
    • 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
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • 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
    • C10M2207/283—Esters of polyhydroxy compounds
    • 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
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

  • esters so-called ester oils
  • ester oils have found increasing use as high-quality lubricating oils in recent years.
  • diesters of dibasic carboxylic acids with monohydric alcohols for example dioctyl sebacate
  • esters of polyols with monobasic acids such as trimethylolpropane tripelargonate
  • polyols e.g. uses trimethylolpropane, neopentyl glycol and / or pentaerythritol.
  • the good suitability of the synthetic esters as lubricants results from the fact that they have a more favorable viscosity-temperature behavior than conventional lubricating oils based on mineral oil and that the setting points are significantly lower when comparable viscosities are set.
  • the invention has for its object to provide new synthetic polyol esters, which are particularly suitable for are suitable for use in the field of temperature-resistant lubricating oils such as gear and hydraulic oils as well as lubricating oil dispersions or lubricating greases and can also be optimally adapted to the aforementioned selection criteria.
  • the technical solution to this problem according to the invention is based on the selection of a specific polyol component as the hydroxyl group function for the production of the polyol esters and combines this selection on the side of the hydroxyl group components with a specific selection of mono- and optionally polyfunctional carboxylic acids on the acid side for the production of the new synthetic polyol ester.
  • Class C acids di- and / or tricarboxylic acids in the range from C6 to C54
  • Class D acids difunctional fatty acids which have been prepared by adding acrylic acid to the double bonds of oleic, linoleic and / or linolenic acid,
  • Class E acids Aromatic and / or paraffinic cyclic polycarboxylic acids with 2 to 6 acid functions.
  • the invention relates to the use of the new synthetic polyol esters for the production of temperature-resistant transmission and hydraulic oils as well as lubricating oil dispersions and / or lubricating greases.
  • the selection of the monofunctional carboxylic acid components used for the esterification and, if desired, also used in minor amounts is of crucial importance.
  • the fatty acids used for the esterification can be divided into the classes A to E listed below, the fatty acid classes A and B relating to monocarboxylic acids, while the acid classes C, D and E contain higher-functional carboxylic acids. The following details apply here:
  • Class A acids Branched fatty acids in the C chain range from C8 to C16
  • Class B acids linear fatty acids in the C chain range from C8 to C14, preferably in the range from C8 to C10.
  • the new synthetic polyol esters of the invention can contain exclusively branched fatty acids from class A or else mixtures of branched fatty acids of class A with linear fatty acids from class B as fatty acid components. Details of the preferred mixing ratios are given below.
  • the multifunctional carboxylic acids used together with the branched fatty acids (class A) or with the mixtures of branched and linear fatty acids (classes A + D) can be classified in the following classes:
  • Class C acids di- and / or tricarboxylic acids in the C number range from C6 to C54. Adipic acid, trimethyladipic acid, azelaic acid and / or sebacic acid are particularly preferred here. Further suitable and particularly preferred polyfunctional acids of this class are di- or trimer fatty acids from the polymerization of mono- and / or polyunsaturated fatty acids in the C range from C16 to C22.
  • Class D acids This covers difunctional fatty acids obtained by adding acrylic acids to the double bonds of oleic acid, linoleic acid and / or linolenic acid. Corresponding addition products to the mixtures of the three unsaturated acids mentioned which are obtained in practice are particularly suitable. The preparation of such difunctional acids of this class D is described for example in DE-OS 24 06 401 and DE-OS 22 53 930.
  • Class E acids Cyclic polycarboxylic acids of aromatic and / or paraffinic nature with 2 to 6 acid functions. Particularly preferred here are terephthalic acid, trimellitic acid, pyromellitic acid and / or cyclohexane carboxylic acid, which can be used as such or in the form of their anhydrides for the preparation of the new synthetic polyol esters.
  • synthetic polyol esters of the type mentioned with the lowest possible acid numbers are preferred, neutral esters or those with a limited excess of free hydroxyl groups are particularly affected.
  • 6.0 to 7.2 equivalents (corresponding to 1 to 1.2 mol) of dipentaerythritol are used in the preparation of the esters per 6 equivalents of the acids or acid mixtures used.
  • Preferred polyol esters of this type show hydroxyl numbers in the range from 0 to about 25.
  • Esters preferred according to the invention furthermore have viscosity values at 40 ° C. in the range from 50 to 1000 mm 2 / s and have pour points in the range from approximately 0 to -30 ° C.
  • branched fatty acids (acid class A) - especially when using 2-ethyl-hexanoic acid, isononanoic acid, isodecanoic acid and / or isotridecanoic acid - esters in the viscosity class range (definition according to ISO 3448 or DIN 51 519) ISO VG 320 to 460.
  • the viscosity of the polyol esters produced is reduced to the viscosity class range ISO VG 46 to ISO VG 220. If you want to increase the viscosity of the esters, the use of dibasic and polybasic acids from the acid classes C, D and / or E indispensable.
  • the new polyol esters according to the invention are suitable carrier oils for temperature-resistant lubricating oil dispersions and greases and are also due to their good tribological properties - for example an excellent pressure absorption capacity - also as an addition components or used alone for hydraulic and gear oils.
  • Usual additives such as oxidation and corrosion inhibitors, dispersants, high pressure additives, anti-foaming agents, metal deactivators and other additives can be added in the usual effective amounts.
  • Dipentaerythritol and the selected fatty acid mixture are esterified in the presence of 0.5% tin grinding at 240 ° C. for 6 to 8 hours while distilling off the water formed in the reaction. Towards the end of the reaction, esterification continues at the same temperature but under reduced pressure. After cooling to 120 ° C., 1 percent by weight of activated bleaching earth is added, the mixture is heated again to 200 ° C. and excess monocarboxylic acid is distilled off in vacuo. After cooling, the reaction mixture is filtered.
  • Viscosity index approx. 90
  • the temperature / weight analysis gives the mass loss of the substance in percent, which occurs when heated with a continuous temperature rise of 20 ° C per minute.
  • Viscosity index approx. 120 Pour point: approx. - 30 ° C

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
EP87118481A 1986-12-22 1987-12-14 Esters de polyols neutres ayant une viscosité élevée Expired - Lifetime EP0272575B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3643935 1986-12-22
DE3643935A DE3643935C2 (de) 1986-12-22 1986-12-22 Synthetische Polyolester

Publications (4)

Publication Number Publication Date
EP0272575A2 true EP0272575A2 (fr) 1988-06-29
EP0272575A3 EP0272575A3 (en) 1989-08-09
EP0272575B1 EP0272575B1 (fr) 1992-09-16
EP0272575B2 EP0272575B2 (fr) 1995-12-13

Family

ID=6316900

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87118481A Expired - Lifetime EP0272575B2 (fr) 1986-12-22 1987-12-14 Esters de polyols neutres ayant une viscosité élevée

Country Status (9)

Country Link
US (1) US5057247A (fr)
EP (1) EP0272575B2 (fr)
JP (1) JP2661927B2 (fr)
AT (1) ATE80607T1 (fr)
BR (1) BR8706979A (fr)
CA (1) CA1317974C (fr)
DE (2) DE3643935C2 (fr)
ES (1) ES2052537T5 (fr)
MX (1) MX169267B (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0406479A1 (fr) * 1989-07-05 1991-01-09 Japan Energy Corporation Lubrifiants pour la réfrigération
EP0518567A1 (fr) * 1991-06-07 1992-12-16 Hatco Corporation Base lubrifiante synthétique formée à partir de mélanges d'acides dont une grande partie à chaînes ramifiées
WO1994021581A1 (fr) * 1993-03-15 1994-09-29 Henkel Kommanditgesellschaft Auf Aktien Polyolethers a pont d'alkylene et leurs esters
WO1996017909A1 (fr) * 1994-12-08 1996-06-13 Exxon Chemical Patents Inc. Bases constituees d'esters synthetiques ramifies biodegradables et lubrifiants fabriques a partir d'elles
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
EP0890634A1 (fr) * 1997-07-09 1999-01-13 Voith Turbo GmbH & Co. KG Fluide de travail pour machine hydrodynamique
US6029459A (en) * 1990-11-16 2000-02-29 Hitachi, Ltd. Refrigeration cycle

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3927155A1 (de) * 1989-08-17 1991-02-21 Henkel Kgaa Umweltfreundliches grundoel fuer die formulierung von hydraulikoelen
US20030104956A1 (en) * 1994-04-28 2003-06-05 Schaefer Thomas G. Synthetic lubricant base stock formed from high content branched chain acid mixtures
JP3001679B2 (ja) * 1991-07-19 2000-01-24 出光興産株式会社 ２サイクルエンジンまたはロータリーエンジン用潤滑油組成物
DE4214653A1 (de) * 1992-05-02 1993-11-04 Henkel Kgaa Motorengrundoele mit verbesserter dichtungsvertraeglichkeit
ATE194641T1 (de) * 1992-06-03 2000-07-15 Henkel Corp Polyolester als schmiermittel für hochtemperatur- kältekompressoren
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
ATE184310T1 (de) * 1992-06-03 1999-09-15 Henkel Corp Polyol/ester-gemisch als schmiermittel für wärmeträgerflüssigkeiten in kälteanlagen
US5976399A (en) 1992-06-03 1999-11-02 Henkel Corporation Blended polyol ester lubricants for refrigerant heat transfer fluids
JP2613526B2 (ja) * 1992-07-04 1997-05-28 花王株式会社 冷凍機作動流体用組成物
AU674024B2 (en) * 1992-08-28 1996-12-05 Henkel Corporation Biodegradable two-cycle engine oil compositions and ester base stocks
US6656888B1 (en) * 1992-08-28 2003-12-02 Cognis Corporation Biodegradable two-cycle engine oil compositions, grease compositions, and ester base stocks use therein
US5458794A (en) * 1993-09-30 1995-10-17 The Lubrizol Corporation Lubricants containing carboxylic esters from polyhydroxy compounds, suitable for ceramic-containing engines
DE69531614T2 (de) * 1994-05-23 2004-06-17 Cognis Corp. Erhöhung des spezifischen elektrischen widerstandes von esterschmiermitteln
US5665686A (en) * 1995-03-14 1997-09-09 Exxon Chemical Patents Inc. Polyol ester compositions with unconverted hydroxyl groups
TW349119B (en) * 1996-04-09 1999-01-01 Mitsubishi Gas Chemical Co Polyol ester based-lubricant
DE19616733C2 (de) * 1996-04-26 2000-07-13 Stockhausen Chem Fab Gmbh Verfahren zur thermisch-mechanischen Oberflächenbehandlung von flächenförmigen Materialbahnen, insbesondere aus Papier und Karton unter Verwendung von Abhäsivmitteln
US5728658A (en) * 1996-05-21 1998-03-17 Exxon Chemical Patents Inc Biodegradable synthetic ester base stocks formed from branched oxo acids
US5798322A (en) * 1996-08-30 1998-08-25 Gateway Additive Company Friction-modifying additives for slideway lubricants
US5942475A (en) * 1996-09-06 1999-08-24 Exxon Chemical Patents Inc. Engine oil lubricants formed from complex alcohol esters
US5922658A (en) * 1996-09-06 1999-07-13 Exxon Chemical Patents Inc. Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks
US5698502A (en) * 1996-09-11 1997-12-16 Exxon Chemical Patents Inc Polyol ester compositions with unconverted hydroxyl groups for use as lubricant base stocks
DE69816843T2 (de) * 1997-10-01 2004-04-15 Unichema Chemie B.V. Komplexaster, diese enthaltende zusammensetzungen und ihre verwendung
US20060229409A1 (en) * 2005-04-08 2006-10-12 Ilmenev Pavel E Method for preparing polyurethane dispersions
DE102006027602A1 (de) * 2006-06-13 2007-12-20 Cognis Ip Management Gmbh Schmierstoffzusammensetzungen enthaltend Komplexester
US9481852B2 (en) * 2008-01-24 2016-11-01 The Lubrizol Corporation High viscosity synthetic ester lubricant base stock blends
US10336958B2 (en) 2016-08-30 2019-07-02 Resinate Materials Group, Inc. Sustainable base oils for lubricants
WO2018110142A1 (fr) 2016-12-13 2018-06-21 花王株式会社 Huile de base lubrifiante et composition lubrifiante comprenant ladite huile de base lubrifiante
JP2018095840A (ja) 2016-12-13 2018-06-21 花王株式会社 潤滑油基油、および該潤滑油基油を含有する潤滑油組成物
JP6928445B2 (ja) 2016-12-21 2021-09-01 花王株式会社 潤滑油基油、該潤滑油基油を含有する潤滑油組成物およびその製造方法
JP7216563B2 (ja) * 2019-02-12 2023-02-01 花王株式会社 グリース基油、および該グリース基油を含有するグリース組成物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1281422B (de) * 1963-06-12 1968-10-31 Drew Chem Corp Verfahren zur Herstellung von als Hochleistungsschmiermittel dienenden Veresterungsprodukten des Pentaerythrits mit Gemischen gesaettigter Fettsaeuren
GB1481270A (en) * 1975-12-31 1977-07-27 Hercules Inc Synthetic oil lubricant
US4175045A (en) * 1978-02-27 1979-11-20 Stauffer Chemical Company Compressor lubrication
US4234497A (en) * 1979-04-30 1980-11-18 Standard Lubricants, Inc. Iso-palmitate polyol ester lubricants

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB644597A (en) * 1946-08-17 1950-10-11 Bakelite Corp Mixed esters
GB663566A (en) * 1948-12-01 1951-12-27 George Bruce Ingram Improvements in or relating to the production of organic carboxylic esters of polyhydric alcohols
US3000917A (en) * 1957-03-15 1961-09-19 Drew & Co Inc E F Linear mixed ester lubricants
BE596980A (fr) * 1959-11-11
GB1122466A (en) * 1966-01-12 1968-08-07 Exxon Research Engineering Co Complex esters
IL32628A0 (en) * 1968-07-18 1969-09-25 Stauffer Chemical Co Pentaerythritol ester lubricants
US3708522A (en) * 1969-12-29 1973-01-02 Lubrizol Corp Reaction products of high molecular weight carboxylic acid esters and certain carboxylic acid acylating reactants
US3753968A (en) * 1971-07-01 1973-08-21 Westvaco Corp Selective reaction of fatty acids and their separation
CA1016539A (fr) * 1973-02-12 1977-08-30 Benjamin F. Ward Methode de fabrication de l'acide dicarboxylique a partir d'acide linoleique contenant un melange d'acides gras
US4049563A (en) * 1973-06-18 1977-09-20 Chevron Research Company Jet engine oils containing extreme pressure additive
JPS5321068B2 (fr) * 1973-10-22 1978-06-30
DE2538232C2 (de) * 1975-08-28 1982-03-11 Dynamit Nobel Ag, 5210 Troisdorf Grenzflächenaktive, flüssige, hydroxylhaltige Estergemische
JPS536350A (en) * 1976-07-08 1978-01-20 Riken Vitamin Co Ltd Lubricants and compositions for molding plastics
JPS5421806A (en) * 1977-07-20 1979-02-19 Fuji Photo Film Co Ltd Magnetic recording medium
SU739083A1 (ru) * 1978-02-22 1980-06-05 Предприятие П/Я Р-6711 Смазочна композици
JPS552659A (en) * 1978-06-22 1980-01-10 Lion Corp Continuous preparation of polyhydric alcohol complete ester
US4277417A (en) * 1978-12-29 1981-07-07 Exxon Research & Engineering Co. Hydrocarbon soluble sulfonated polyols, esters of hydrocarbon substituted C4 -C10 dicarboxylic acids with polyols and sulfonic acid, processes therefor, and lubricating compositions thereof
JPS5651433A (en) * 1979-10-04 1981-05-09 Nippon Kayaku Co Ltd Preparation of mixture of dipentaerythritol esters
US4477383A (en) * 1982-05-05 1984-10-16 National Distillers And Chemical Corporation Di- and tripentaerythritol esters of isostearic acid
US4589900A (en) * 1983-03-17 1986-05-20 United Technologies Corporation High-strength thermally stable magnesium aluminosilicate glass-ceramic matrix sic fiber composite
US4589990A (en) * 1985-06-21 1986-05-20 National Distillers And Chemical Corporation Mist lubricant compositions
US4645615A (en) * 1986-02-27 1987-02-24 Fmc Corporation Fire-resistant hydraulic fluid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1281422B (de) * 1963-06-12 1968-10-31 Drew Chem Corp Verfahren zur Herstellung von als Hochleistungsschmiermittel dienenden Veresterungsprodukten des Pentaerythrits mit Gemischen gesaettigter Fettsaeuren
GB1481270A (en) * 1975-12-31 1977-07-27 Hercules Inc Synthetic oil lubricant
US4175045A (en) * 1978-02-27 1979-11-20 Stauffer Chemical Company Compressor lubrication
US4234497A (en) * 1979-04-30 1980-11-18 Standard Lubricants, Inc. Iso-palmitate polyol ester lubricants

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0406479A1 (fr) * 1989-07-05 1991-01-09 Japan Energy Corporation Lubrifiants pour la réfrigération
EP0480479A2 (fr) * 1989-07-05 1992-04-15 Japan Energy Corporation Lubrifiants pour la refrigeration
EP0480479A3 (en) * 1989-07-05 1992-06-17 Kyodo Oil Technical Research Center Co., Ltd. Refrigeration lubricants
EP0536814A1 (fr) * 1989-07-05 1993-04-14 Japan Energy Corporation utilisation d'un lubrifiant pour compresseurs utilisant un réfrigérant hydrofluorocarboné ne contenant pas de chlore.
US6029459A (en) * 1990-11-16 2000-02-29 Hitachi, Ltd. Refrigeration cycle
EP0518567A1 (fr) * 1991-06-07 1992-12-16 Hatco Corporation Base lubrifiante synthétique formée à partir de mélanges d'acides dont une grande partie à chaînes ramifiées
US5833876A (en) * 1992-06-03 1998-11-10 Henkel Corporation Polyol ester lubricants for refrigerating compressors operating at high temperatures
US5853609A (en) * 1993-03-10 1998-12-29 Henkel Corporation Polyol ester lubricants for hermetically sealed refrigerating compressors
WO1994021581A1 (fr) * 1993-03-15 1994-09-29 Henkel Kommanditgesellschaft Auf Aktien Polyolethers a pont d'alkylene et leurs esters
WO1996017909A1 (fr) * 1994-12-08 1996-06-13 Exxon Chemical Patents Inc. Bases constituees d'esters synthetiques ramifies biodegradables et lubrifiants fabriques a partir d'elles
US5817607A (en) * 1994-12-08 1998-10-06 Exxon Chemical Patents Inc. Biodegradable branched synthetic ester base stocks and lubricants formed therefrom
EP0890634A1 (fr) * 1997-07-09 1999-01-13 Voith Turbo GmbH & Co. KG Fluide de travail pour machine hydrodynamique

Also Published As

Publication number Publication date
ATE80607T1 (de) 1992-10-15
DE3643935A1 (de) 1988-06-23
EP0272575B2 (fr) 1995-12-13
BR8706979A (pt) 1988-07-26
US5057247A (en) 1991-10-15
ES2052537T5 (es) 1996-03-01
DE3781782D1 (de) 1992-10-22
JPS63170337A (ja) 1988-07-14
CA1317974C (fr) 1993-05-18
DE3643935C2 (de) 1995-07-06
JP2661927B2 (ja) 1997-10-08
EP0272575B1 (fr) 1992-09-16
MX169267B (es) 1993-06-28
EP0272575A3 (en) 1989-08-09
ES2052537T3 (es) 1994-07-16

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