GB971901A - Improvements in organic esters and in lubricants consisting of or containing them - Google Patents

Improvements in organic esters and in lubricants consisting of or containing them

Info

Publication number
GB971901A
GB971901A GB38232/59A GB3823259A GB971901A GB 971901 A GB971901 A GB 971901A GB 38232/59 A GB38232/59 A GB 38232/59A GB 3823259 A GB3823259 A GB 3823259A GB 971901 A GB971901 A GB 971901A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
acid
mixture
saturated aliphatic
specified
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.)
Expired
Application number
GB38232/59A
Inventor
Stuart Walter Critchley
Peter Michael Blanchard
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.)
BP PLC
Geigy Co Ltd
Original Assignee
BP PLC
Geigy Co Ltd
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 to NL257845D priority Critical patent/NL257845A/xx
Priority to BE596980D priority patent/BE596980A/xx
Application filed by BP PLC, Geigy Co Ltd filed Critical BP PLC
Priority to GB38232/59A priority patent/GB971901A/en
Priority to FR843368A priority patent/FR1273178A/en
Priority to DEC22706A priority patent/DE1264659B/en
Priority to CH1262560A priority patent/CH436245A/en
Publication of GB971901A publication Critical patent/GB971901A/en
Expired legal-status Critical Current

Links

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
    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • 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
    • C10M2207/284—Esters of aromatic 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
    • C10M2207/285—Esters of aromatic polycarboxylic 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
    • C10M2207/286—Esters of polymerised unsaturated 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no 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
    • 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
    • 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
    • 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
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/04—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having a silicon-to-carbon bond, e.g. organo-silanes
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines

Abstract

Fully esterified liquid complex ester compositions are prepared by reacting in one or more stages (a) a saturated aliphatic non-hydroxylated mono-carboxylic acid with 1-18 carbon atoms, or an aromatic non-hydroxylated mono-carboxylic acid with 7-15 carbon atoms not containing any unsaturated nuclear substituent or a mixture thereof, (b) a saturated aliphatic polyhydric alcohol with 5-15 carbon atoms with no hydrogen atom attached to any carbon atom in a -2 position with respect to any hydroxyl group of the formula <FORM:0971901/C1/1> wherein R2 is alkyl with 2-4 carbon atoms or CH2OR3 wherein R3 is hydrogen or completes a di- or tripentaerythritol molecule and (c) a saturated aliphatic non-hydroxylated dicarboxylic acid with 4-14 carbon atoms or a mixture thereof. Specified polyols are 1,1,1 trimethylol propane pentaerythritol, di- and tri-pentaerythritol but polyols of formula <FORM:0971901/C1/2> such as neopentyl glycol may be admixed with the specified polyols. The esterification may be effected as a one stage process where all three components are refluxed together, a two stage process where the alcohol (b) is partially esterified with the monocarboxylic acid (a) and then heated with the dicarboxylic acid (c) or a three stage process where part of the alcohol (b) is reacted with the mono-acid (a) and the remainder of (b) reacted with the di-acid (c) and the partial esters refluxed together. The preferred proportions of a:b:c are 2-20:2:0.25-1.5 and the above reactions may be carried out in the presence of an esterification catalyst e.g. p-toluene sulphonic acid, sodium bisulphate, potassium pyrosulphate, a tetraalkyl titanate, titanium tetrachloride or a molecular sieve and a water entrainer such as benzene or toluene may be added. The preferred reactants are (a) a saturated straight chain fatty acid with 7-10 carbon atoms or a mixture thereof, (b) 1:1:1 trimethylol propane and (c) sebacic acid. The esters may be used as lubricants or may be blended with neutral simple esters and used as lubricants. Specified monocarboxylic acids are capric, n-valeric, isovaleric, enanthic, caprylic, pelargonic, propionic and benzoic while specified dicarboxylic acids are adipic, sebacic and azelaic. Specifications 892,943 and 894,639 are referred to.ALSO:Fully esterified liquid complex ester compositions are prepared by reacting in one or more stages (a) a saturated aliphatic non-hydroxylated mono-carboxylic acid with 1-18 carbon atoms, or an aromatic non-hydroxylated mono-carboxylic acid with 7-15 carbon atoms not containing any unsaturated nuclear substituent or a mixture thereof, (b) a saturated aliphatic polyhydric alcohol with 5-15 carbon atoms with no hydrogen atom attached to any carbon atom in a -2 position with respect to any hydroxyl group of the formula <FORM:0971901/C3/1> wherein R2 is alkyl with 2-4 carbon atoms or CH2OR3 wherein R3 is hydrogen or completes a di- or tripentaerythritol molecule and (c) a saturated aliphatic non-hydroxylated dicarboxylic acid with 4-14 carbon atoms or a mixture thereof. Specified polyols are 1,1,1 trimethylol propane pentaerythritol, di- and tripentaerythritol but polyols of formula <FORM:0971901/C3/2> such as neopentyl glycol may be admixed with the specified polyols. The esterification may be effected as a one stage process where all three components are refluxed together, a two stage process where the alcohol (b) is partially esterified with the monocarboxylic acid (a) and then heated with the dicarboxylic acid (c) or a three stage process where part of the alcohol (b) is reacted with the mono-acid (a) and the remainder of (b) reacted with the di-acid (c) and the partial esters refluxed together. The preferred proportions of a:b:c: are 2-20:2:0.25-1.5 and the above reactions may be carried out in the presence of an esterification catalyst e.g. p-toluene sulphonic acid, sodium bisulphate, potassium pyrosulphate, a tetraalkyl titanate, titanium tetrachloride or a molecular sieve and a water entrainer such as benzene or toluene may be added. The preferred reactants are (a) a saturated straight chain fatty acid with 7-10 carbon atoms or a mixture thereof, (b) 1:1:1 trimethylol propane and (c) sebacic acid. The esters may be used as lubricants or may be blended with neutral simple esters and, possibly, anti-oxidants (e.g. phenothiazine, phenyl-alpha-naphthylamine of 5-ethyl-10, 10-diphenyl-phenazasilane and used as lubricants. Specified monocarboxylic acids are capric, n-valeric, isovaleric, enanthic, caprylic, pelargonic, propionic and benzoic while specified dicarboxylic acids are adipic, sebacic and azelaic. Specifications 892,943 and 894,639 are referred to.ALSO:A lubricant blend comprises two components, one component being one or more fully esterified liquid complex ester compositions prepared by reacting in one or more stages: (a) a saturated aliphatic non-hydroxylated monocarboxylic with 1-18 carbon atoms or an aromatic nonhydroxylated monocarboxylic acid with 7 to 15 carbon atoms and not containing any unsaturated nuclear substituent or a mixture thereof, (b) a saturated aliphatic polyol with 5 to 15 carbon atoms, having no hydrogen attached to any carbon in a 2-position with respect to any hydroxyl group and of formula <FORM:0971901/C4-C5/1> wherein R1 and R2 are alkyl with 1 to 4 carbon atoms, or R1 is methylol and R2 is alkyl with 2 to 4 carbon atoms or -CH2OR3 (wherein R3 is hydrogen or completes di- or tri-pentaerythritol) and (c) a saturated aliphatic nonhydroxylated dicarboxylic acid with 4-14 carbon atoms or a mixture thereof and the other component being (1) one or more liquid fully esterified simple esters of a saturated aliphatic polyhydric primary alcohol or a mixture thereof with a saturated aliphatic or aromatic non-hydroxylated monocarboxylic acid or a mixture thereof, or (2) a simple ester with an alcohol as in (1) with a saturated aliphatic or aromatic non-hydroxylated polycarboxylic acid or a mixture thereof, or (3) a mixture of simple esters of types (1) and (2) so that the relative proportions of the two components is such that the viscosity is from 3 to 15 centistokes at 210 DEG F. Specified polyhydric alcohols are 1,1,1-trimethylolpropane pentaerythritol, di- and tri-pentaerythritol or a mixture of neopentyl glycol with 1,1,1-trimethylolpropane. Specified monocarboxylic acids are capric, n-valeric, isovaleric, enanthic, caprylic, pelargonic, propionic and benzoic while specified dicarboxylic acids are adipic sebacic and azelaic. The preferred complex ester is prepared by reacting (d) a saturated straight chain fatty acid of 7-10 carbon atoms or a mixture thereof, (e) 1,1,1-trimethylol propane and (f) sebacic acid. Specifications 892,943 and 894,639 are referred to
GB38232/59A 1959-11-11 1959-11-11 Improvements in organic esters and in lubricants consisting of or containing them Expired GB971901A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL257845D NL257845A (en) 1959-11-11
BE596980D BE596980A (en) 1959-11-11
GB38232/59A GB971901A (en) 1959-11-11 1959-11-11 Improvements in organic esters and in lubricants consisting of or containing them
FR843368A FR1273178A (en) 1959-11-11 1960-11-08 Liquid lubricant complex ester and its manufacturing process
DEC22706A DE1264659B (en) 1959-11-11 1960-11-10 Lubricants for aircraft gas turbines
CH1262560A CH436245A (en) 1959-11-11 1960-11-11 Process for the preparation of liquid, mixed esters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB38232/59A GB971901A (en) 1959-11-11 1959-11-11 Improvements in organic esters and in lubricants consisting of or containing them
GB630960 1960-02-23

Publications (1)

Publication Number Publication Date
GB971901A true GB971901A (en) 1964-10-07

Family

ID=26240600

Family Applications (1)

Application Number Title Priority Date Filing Date
GB38232/59A Expired GB971901A (en) 1959-11-11 1959-11-11 Improvements in organic esters and in lubricants consisting of or containing them

Country Status (5)

Country Link
BE (1) BE596980A (en)
CH (1) CH436245A (en)
DE (1) DE1264659B (en)
GB (1) GB971901A (en)
NL (1) NL257845A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5420266A (en) * 1977-07-15 1979-02-15 Miyoshi Yushi Kk Ester lubricating oil composition
NL8100954A (en) * 1980-02-29 1981-10-01 Perstorp Ab LUBRICANT FOR METAL WORKING.
US5057247A (en) * 1986-12-22 1991-10-15 Henkel Kommanditgesellschaft Auf Aktien High-viscosity, neutral polyol esters
US5411672A (en) * 1992-09-15 1995-05-02 Nippon Oil Co., Ltd. Lubrication oil composition
EP0656931A1 (en) * 1992-08-28 1995-06-14 Henkel Corporation Biodegradable two-cycle engine oil compositions and ester base stocks
WO2009083551A1 (en) * 2007-12-28 2009-07-09 Biorefinery.De Gmbh Process for preparing carboxylic esters

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3255128B1 (en) * 2016-06-08 2021-12-01 Peter Greven GmbH & Co. KG Complex esters and their use

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2628974A (en) * 1948-03-27 1953-02-17 Texas Co Polyester synthetic lubricants
GB680438A (en) * 1948-10-01 1952-10-08 Standard Oil Dev Co Complex glycol esters for use as or in lubricants
US2499983A (en) * 1948-12-16 1950-03-07 Rohm & Haas Polyester lubricants
US2617779A (en) * 1949-05-28 1952-11-11 Gen Electric Plasticized vinyl halide resins and electrical conductors insulated therewith
GB697412A (en) * 1950-12-22 1953-09-23 Standard Oil Dev Co Improvements in or relating to synthetic ester lubricant
US2588194A (en) * 1950-12-22 1952-03-04 Standard Oil Dev Co Synthetic lubricant
GB756959A (en) * 1953-10-20 1956-09-12 Exxon Research Engineering Co Synthetic lubricants
US2860119A (en) * 1953-11-17 1958-11-11 American Cyanamid Co Alkyd resins, their preparation, and compositions thereof with aminoplast resins
US2764551A (en) * 1954-05-17 1956-09-25 Exxon Research Engineering Co Ashless detergent additive for lubricating oils

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5420266A (en) * 1977-07-15 1979-02-15 Miyoshi Yushi Kk Ester lubricating oil composition
JPS6213394B2 (en) * 1977-07-15 1987-03-26 Myoshi Yushi Kk
NL8100954A (en) * 1980-02-29 1981-10-01 Perstorp Ab LUBRICANT FOR METAL WORKING.
DE3107052A1 (en) * 1980-02-29 1981-12-24 Perstorp AB, 28400 Perstorp CONNECTIONS FOR WATER-DUMBABLE METAL WORKING LUBRICANTS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN METAL WORKING LIQUIDS
US5057247A (en) * 1986-12-22 1991-10-15 Henkel Kommanditgesellschaft Auf Aktien High-viscosity, neutral polyol esters
EP0656931A1 (en) * 1992-08-28 1995-06-14 Henkel Corporation Biodegradable two-cycle engine oil compositions and ester base stocks
EP0656931A4 (en) * 1992-08-28 1997-05-02 Henkel Corp Biodegradable two-cycle engine oil compositions and ester base stocks.
US5411672A (en) * 1992-09-15 1995-05-02 Nippon Oil Co., Ltd. Lubrication oil composition
WO2009083551A1 (en) * 2007-12-28 2009-07-09 Biorefinery.De Gmbh Process for preparing carboxylic esters

Also Published As

Publication number Publication date
DE1264659B (en) 1968-03-28
BE596980A (en)
CH436245A (en) 1967-05-31
NL257845A (en)

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