WO2014124698A1 - Lubrifiant d'ester destiné à des applications de lubrifiant de champ pétrolier et d'autres d'applications de lubrifiant industriel - Google Patents

Lubrifiant d'ester destiné à des applications de lubrifiant de champ pétrolier et d'autres d'applications de lubrifiant industriel Download PDF

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Publication number
WO2014124698A1
WO2014124698A1 PCT/EP2013/053214 EP2013053214W WO2014124698A1 WO 2014124698 A1 WO2014124698 A1 WO 2014124698A1 EP 2013053214 W EP2013053214 W EP 2013053214W WO 2014124698 A1 WO2014124698 A1 WO 2014124698A1
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acid
ester
polyol
lubricant composition
lubricant
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PCT/EP2013/053214
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English (en)
Inventor
Heinz Müller
Diana MÄKER
Nadja Herzog
Tanja LÜDTKE
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Amril Ag
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Priority to PCT/EP2013/053214 priority Critical patent/WO2014124698A1/fr
Publication of WO2014124698A1 publication Critical patent/WO2014124698A1/fr

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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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C10M107/34—Polyoxyalkylenes
    • 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
    • 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
    • C10M2207/2835—Esters of polyhydroxy compounds used as base material
    • 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
    • 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
    • C10M2209/1033—Polyethers, i.e. containing di- or higher polyoxyalkylene groups used as base material
    • 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
    • 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
    • C10M2209/105—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only
    • C10M2209/1055—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing three carbon atoms only used as base material
    • 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
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/64—Environmental friendly compositions
    • 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
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants

Definitions

  • the present invention relates to a lubricant composition
  • a lubricant composition comprising an optionally cross- linked ester obtainable by reacting a polyol alkoxylate with a monocarboxylic acid.
  • Further aspects of the invention relate to a tetraester obtainable by reacting a polyol alkoxylate with a monocarboxylic acid and uses of said composition and tetraester.
  • Lubricants with improved biodegradability are desirable for example for equipment used in certain resource industries, such as forestry, mining, petroleum exploration and production in particular wherever the lubricants themselves might come into contact with the environment.
  • resource industries such as forestry, mining, petroleum exploration and production
  • Such a large percentage coupled with ecological concerns has led to resurgence in the use of biodegradable feedstocks.
  • PAO polyalphaolefin
  • the present invention provides a lubricant composition
  • a lubricant composition comprising an ester obtainable by reacting at least
  • ester is cross-linked or not cross-linked.
  • a tetraester obtainable by reacting
  • polyol alkoxylate and said monocarboxylic acid are as defined herein in the context of the lubricant composition.
  • One aspect of the invention relates to an ester with at least four ester groups obtainable by reacting
  • a further aspect of the invention relates to the use of an ester of the invention as a lubricant, wherein the lubricant is preferably selected from the group consisting of engine oil, oil drilling fluid, hydraulic oil, compressor oil, gear oil, bearing oil, low temperature lubricant and turbine oil.
  • alkyl refers to a saturated straight or branched carbon chain.
  • an alkyl as used herein is a C1-C20 alkyl and more preferably is a C1-C10 alkyl, i.e. having 1 , 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms, e.g.
  • Alkyl groups are optionally substituted.
  • Alcohol refers to a compound having one or more hydroxyl groups.
  • a C8-C36 alkyl alcohol is a C8-C36 alkyl substituted with one or more hydroxyl groups.
  • polyol refers to an alcohol having at least two hydroxyl groups.
  • heteroalkyl refers to a saturated straight or branched carbon chain.
  • the chain comprises from 1 to 9 carbon atoms, i.e. 1, 2, 3, 4, 5, 6, 7, 8, 9 e.g. methyl, ethyl, propyl, z ' so-propyl, butyl, z ' so-butyl, sec-butyl, tert-butyl, pentyl or hexyl, heptyl, octyl, nonyl which is interrupted one or more times, e.g. 1, 2, 3, 4, 5, with the same or different heteroatoms.
  • the heteroatoms are selected from O, S, and N, e.g.
  • cycloalkyl and “heterocycloalkyl”, by themselves or in combination with other terms, represent, unless otherwise stated, cyclic versions of “alkyl” and “heteroalkyl”, respectively, with preferably 3, 4, 5, 6, 7, 8, 9 or 10 atoms forming a ring, e.g. cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl etc.
  • cycloalkyl and “heterocycloalkyl” are also meant to include bicyclic, tricyclic and polycyclic versions thereof.
  • heterocycloalkyl preferably refers to a saturated ring having five members of which at least one member is a N, O or S atom and which optionally contains one additional O or one additional N; a saturated ring having six members of which at least one member is a N, O or S atom and which optionally contains one additional O or one additional N or two additional N atoms; or a saturated bicyclic ring having nine or ten members of which at least one member is a N, O or S atom and which optionally contains one, two or three additional N atoms.
  • Cycloalkyl and “heterocycloalkyl” groups are optionally substituted. Additionally, for heterocycloalkyl, a heteroatom can occupy the position at which the heterocycle is attached to the remainder of the molecule.
  • Preferred examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, spiro[3,3]heptyl, spiro[3,4]octyl, spiro[4,3]octyl, spiro[3,5]nonyl, spiro[5,3]nonyl, spiro[3,6]decyl, spiro[6,3]decyl, spiro[4,5]decyl, spiro[5,4]decyl, bicyclo[4.
  • heterocycloalkyl examples include 1 -(1,2,5, 6- tetrahydropyridyl), 1-piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-morpholinyl, 3-morpholinyl, 1,8 diaza-spiro-[4,5] decyl, 1,7 diaza-spiro-[4,5] decyl, 1,6 diaza-spiro-[4,5] decyl, 2,8 diaza- spiro[4,5] decyl, 2,7 diaza-spiro[4,5] decyl, 2,6 diaza-spiro[4,5] decyl, 1,8 diaza-spiro-[5,4] decyl, 1,7 diaza-spiro-[5,4] decyl, 2,8 diaza-spiro-[5,4] decyl, 2,7 diaza-spiro[5,4] decyl, 3,8 diaza-spiro[5,4] decyl, 3,7 diaza-
  • alicyclic system refers to mono, bicyclic, tricyclic or polycyclic version of a cycloalkyl or heterocycloalkyl comprising at least one double and/or triple bond.
  • an alicyclic system is not aromatic or heteroaromatic, i.e. does not have a system of conjugated double bonds/free electron pairs.
  • the number of double and/or triple bonds maximally allowed in an alicyclic system is determined by the number of ring atoms, e.g. in a ring system with up to 5 ring atoms an alicyclic system comprises up to one double bond, in a ring system with 6 ring atoms the alicyclic system comprises up to two double bonds.
  • cycloalkenyl as defined below is a preferred embodiment of an alicyclic ring system.
  • Alicyclic systems are optionally substituted.
  • aryl preferably refers to an aromatic monocyclic ring containing 6 carbon atoms, an aromatic bicyclic ring system containing 10 carbon atoms or an aromatic tricyclic ring system containing 14 carbon atoms. Examples are phenyl, naphtyl or anthracenyl.
  • the aryl group is optionally substituted.
  • aralkyl refers to an alkyl moiety, which is substituted by aryl, wherein alkyl and aryl have the meaning as outlined above. An example is the benzyl radical.
  • the alkyl chain comprises from 1 to 8 carbon atoms, i.e. 1, 2, 3, 4, 5, 6, 7, or 8, e.g. methyl, ethyl methyl, ethyl, propyl, z ' so-propyl, butyl, z ' so-butyl, sec-butenyl, tert-butyl, pentyl or hexyl, pentyl, octyl.
  • the aralkyl group is optionally substituted at the alkyl and/or aryl part of the group.
  • heteroaryl preferably refers to a five or six-membered aromatic monocyclic ring wherein at least one of the carbon atoms are replaced by 1, 2, 3, or 4 (for the five membered ring) or 1, 2, 3, 4, or 5 (for the six membered ring) of the same or different heteroatoms, preferably selected from O, N and S; an aromatic bicyclic ring system wherein 1, 2, 3, 4, 5, or 6 carbon atoms of the 8, 9, 10, 11 or 12 carbon atoms have been replaced with the same or different heteroatoms, preferably selected from O, N and S; or an aromatic tricyclic ring system wherein 1, 2, 3, 4, 5, or 6 carbon atoms of the 13, 14, 15, or 16 carbon atoms have been replaced with the same or different heteroatoms, preferably selected from O, N and S.
  • Examples are oxazolyl, isoxazolyl, 1,2,5-oxadiazolyl, 1,2,3-oxadiazolyl, pyrrolyl, imidazolyl, pyrazolyl, 1,2,3-triazolyl, thiazolyl, isothiazolyl, 1,2,3,-thiadiazolyl, 1,2,5- thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, 1-benzofuranyl, 2-benzofuranyl, indolyl, isoindolyl, benzothiophenyl, 2-benzothiophenyl, 1H- indazolyl, benzimidazolyl, benzoxazolyl, indoxazinyl, 2,1-benzisoxazoyl, benzothiazolyl, 1,2- benzisothiazolyl
  • heteroarylkyl refers to an alkyl moiety, which is substituted by heteroaryl, wherein alkyl and heteroaryl have the meaning as outlined above.
  • An example is the 2- alklypyridinyl, 3-alkylpyridinyl, or 2-methylpyridinyl.
  • the alkyl chain comprises from 1 to 8 carbon atoms, i.e. 1, 2, 3, 4, 5, 6, 7, or 8, e.g.
  • heteroaralkyl group is optionally substituted at the alkyl and/or heteroaryl part of the group.
  • alkenyl and cycloalkenyl refer to olefmic unsaturated carbon atoms containing chains or rings with one or more double bonds. Examples are propenyl and cyclohexenyl.
  • the alkenyl chain comprises from 2 to 8 carbon atoms, i.e. 2, 3, 4, 5, 6, 7, or 8, e.g.
  • the term also comprises CH 2 , i.e. methenyl, if the substituent is directly bonded via the double bond.
  • the cycloalkenyl ring comprises from 3 to 14 carbon atoms, i.e. 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14, e.g.
  • alkynyl refers to unsaturated carbon atoms containing chains or rings with one or more triple bonds.
  • An example is the propargyl radical.
  • the alkynyl chain comprises from 2 to 8 carbon atoms, i.e. 2, 3, 4, 5, 6, 7, or 8, e.g. ethynyl, 1-propynyl, 2- propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, hexynyl, pentynyl, octynyl.
  • a polyol alkoxylate is preferably any compound comprising an alkoxylated polyol.
  • dimer acid or “dimerized fatty acid” refers to dicarboxylic acids prepared by dimerizing unsaturated fatty acids obtained from tall oil, usually on clay catalysts.
  • a preferred dimmer acid is a dimer of a C8-C32 carboxylic acid and most preferably a dimer of oleic acid.
  • substituents e.g. 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 substituents which are in each instance independently selected from the group consisting of halogen, in particular F, CI, Br or I; -NO 2 , -CN, -OR * , -NR'R", -(CO)OR', -(CO)OR'", -(CO)NR'R", -NR'COR” ", -NR'COR', -NR"CONR'R", -NR"S0 2 A, -COR' "; -S0 2 NR'R", -OOCR' ", -CR” 'R” "OH, -R"'OH, and -E;
  • R' and R' ' is each independently selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, -OE, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, and aralkyl or together form a heteroaryl, or heterocycloalkyl; optionally substituted;
  • R' " and R” " is each independently selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, aryl, aralkyl, heteroaryl, and -NR'R";
  • E is selected from the group consisting of alkyl, alkenyl, cycloalkyl, alkoxy, alkoxyalkyl, heterocycloalkyl, an alicyclic system, aryl and heteroaryl; optionally substituted;
  • radicals can be selected independently from each other, then the term "independently" means that the radicals may be the same or may be different.
  • the present invention provides novel lubricants. It was unexpectedly found that the lubricant composition and tetraester of the invention has good lubricating properties, a low pour point, is less toxic and exhibits improved biodegradability.
  • the invention provides a lubricant composition
  • a lubricant composition comprising an ester obtainable by reacting at least
  • ester is cross-linked or not cross-linked.
  • the esters of the invention can be obtained utilizing conventional esterification procedures. This generally involves reacting a molar excess of the carboxylic acid with the polyol alkoxylate at an elevated temperature while removing water.
  • the reaction may be carried out by refluxing the reactants in an azeotroping solvent, such as toluene or xylene, to facilitate removal of water.
  • an azeotroping solvent such as toluene or xylene
  • the reaction is carried out in the absence of solvents.
  • Esterification catalysts may be used but are not necessary for the reaction.
  • the excess acid and (if present) any solvent can be separated from the ester by vacuum stripping or distillation.
  • the ester product thus produced may be utilized as such or it may be alkali refined or otherwise treated to reduce the acid number, remove catalyst residue, reduce the ash content, etc.
  • preferably essentially all of the hydroxyl groups are reacted and the resulting ester products have hydroxyl values (mg KOH/g) less than 10.
  • said ester is a full ester which means that during ester synthesis preferably all free hydroxyl groups of the alcohol reactant are reacted with a monocarboxylic acid such that no free hydroxyl groups remain on the polyol part of the full ester after the reaction.
  • ester of the invention is obtainable by reacting (a) a polyol alkoxylate, (b) a monocarboxylic acid and (c) a polycarboxylic acid wherein said polycarboxylic acid is e.g. a dicarboxylic acid.
  • Useful dicarboxylic acids are preferably selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, dimer acid, and sebacic acid.
  • the molar ratio between said mono- and said polycarboxylic acid during synthesis can for example be 10: 1.
  • ester is not cross-linked.
  • the ester is not cross-linked this means that the reaction mixture comprises less than 0.05 wt% (based on the weight of the reaction mixture) of a polycarboxylic acid and that most preferably the reaction mixture comprises no polycarboxylic acid.
  • the reaction preferably comprises not more than 10 wt% (based on the weight of the reaction mixture) of a polycarboxylic acid.
  • the ester of the invention is not cross linked.
  • said polyol alkoxylate in (a) is obtainable by alkoxylation of a polyol that is a branched or unbrached C4-C40 alkane polyol.
  • said polyol is a branched or unbrached C5-C40 alkane polyol. Most preferably, said alkane polyol is a branched C5-C10 polyol. In a further preferred embodiment, said polyol comprises at least three hydroxyl groups.
  • said polyol is selected from the group consisting of diglycerol, triglycerol, trimethylol ethane, trimethylol propane, trimethylol butane, trimethylol pentane, trimethylol hexane, trimethylol heptane, pentaerythritol, di(pentaerythritol), tri(pentaerythritol), tetra(pentaerythritol), penta(pentaerythritol), dimethylolpropane, dimerdiol, trimertriol and neopentyl glycol.
  • the composition of the invention does not comprise a phosphate ester. It is further preferred that said alkoxylate is a C3-C10 alkoxylate and preferably propoxylate.
  • said polyol alkoxylate in (a) is alkoxylated pentaerythritol which in an even more preferred embodiment has the following structure:
  • R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of C3-C8 alkyl (e.g. C3-, C4-, C5-, C6-, CI- or C8-alkyl) and C3-C8 alkenyl (e.g. C3-, C4-, C5-, C6-, CI- or C8-alkenyl), optionally substituted; and
  • a+b+c+d is an integer number between 1 and 30, preferably between 4 and 10 (e.g. 4, 5, 6, 7, 8, 9 or 10) and most preferably 5.
  • said polyol alkoxylate in (a) has the following structure:
  • a+b+c+d an integer number between 1 and 30, preferably between 4 and 10 (e.g. 4, 5, 6, 7, 8, 9 or 10) and most preferably 5.
  • a lubricant composition of the invention wherein said monocarboxylic acid in (b) is a branched or unbranched, saturated or unsaturated C6-C22 monocarboxylic acid.
  • the monocarboxylic acid is unbranched and aliphatic.
  • a saturated C8-C10 monocarboxylic acid e.g. octanoic acid, nonanoic acid or decanoic acid
  • an unsaturated C16-C18 monocarboxylic acid e.g. palmitoleic acid, sapienic acid, oleic acid or elaidic acid
  • said monocarboxylic acid is aliphatic.
  • said monocarboxylic acid is selected from the group consisting of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, icosanoic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid, linoelaidic acid, a-linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexaenoic acid, hydroxy stearic acid, ricinoleic acid, iso stea
  • said ester is an alkoxylated pentaerythritol saturated or unsaturated C6-C22 monocarboxylic acid tetraester and even more preferably it is an alkoxylated pentaerythritol saturated or unsaturated C8-C18 monocarboxylic acid tetraester.
  • a saturated C8- CIO monocarboxylic acid e.g. octanoic acid, nonanoic acid or decanoic acid
  • an unsaturated C16-C18 monocarboxylic acid e.g.
  • said ester is an alkoxylated pentaerythritol monocarboxylic acid tetraester wherein said monocarboxylic acid is preferably selected from the group consisting of hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, icosanoic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, linoleic acid
  • said monocarboxylic acid in (b) is unsaturated.
  • a further preferred embodiment of the invention relates to a lubricant composition of the invention, wherein said ester has a pour point as measured by DIN ISO 3016(10/82) which is lower than the pour point as measured by DIN ISO 3016(10/82) of an ester produced by reacting said polyol with said monocarboxylic acid whereby said polyol is however not alkoxylated and/or wherein said ester has a biological degradability of greater than 66,5% after 28 days according to the manometric respirometric test defined in OECD 301 F.
  • the ester according to the invention has a pour point as measured by DIN ISO 3016(10/82) which is lower than the pour point as measured by DIN ISO 3016(10/82) for the same ester which however is based on a non-propoxylated polyol. More preferably the ester of the invention has a biological degradability of greater than 67%, 68%, 69%, 70%, 71%, 72%, 73% or greater than 74% after 28 days according to the manometric respirometric test defined in OECD 301 F.
  • said ester has an improved pour point as measured by DIN ISO 3016(10/82) e.g. a pour point of below -35°C and more preferably below -36°C, - 37°C, -38°C, -39°C, -40°C, -4FC, -42°C, -50°C or below -60°C.
  • the polyol alkoxylate in (a) has a hydroxyl number of between 500 and 600 as measured according to DIN 53240-2.
  • a lubricant composition according to the invention, wherein said lubricant composition further comprises a lubricant additive that is different from said ester and that is selected from the group consisting of a further lubricant, a viscosity modifier, a friction modifier, an ashless detergent, a cloud point depressant, a pour point depressant, a demulsifier, a flow improver, an anti-static agent, an ashless antioxidant, an antifoam agent, a corrosion inhibitor, an antiwear agent, a seal swell agent, a lubricity aid, an antimisting agent, an organic solvent, a gel-breaking surfactant and mixtures thereof.
  • a further lubricant that is different from said ester and that is selected from the group consisting of a further lubricant, a viscosity modifier, a friction modifier, an ashless detergent, a cloud point depressant, a pour point depressant, a demulsifier, a flow improver, an
  • the mentioned viscosity modifier is preferably selected from the group consisting of hydrogenated copolymers of styrene-butadiene, ethylene-propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers, polymethacrylates, polyacrylates, polyalkyl styrenes, alkenyl aryl conjugated diene copolymers, polyolefms, esters of maleic anhydride-styrene copolymers, functionalized polyolefms, ethylene-propylene copolymers functionalized with the reaction product of maleic anhydride and an amine, polymethacrylate functionalized with an amine, styrene- maleic anhydride copolymers reacted with an amine, polymethacrylate polymers, esterified polymers, esterified polymers of a vinyl aromatic monomer and an unsaturated carboxy
  • Ashless antioxidants preferably include alkyl-substituted phenols such as 2,6-di-tertiary butyl- 4-methyl phenol, phenate sulfides, phosphosulfurized terpenes, sulfurized esters, aromatic amines, diphenyl amines, alkylated diphenyl amines and hindered phenols, bis-nonylated diphenylamine, nonyl diphenylamine, octyl diphenylamine, bis-octylated diphenylamine, bis- decylated diphenylamine, decyl diphenylamine and mixtures thereof.
  • alkyl-substituted phenols such as 2,6-di-tertiary butyl- 4-methyl phenol, phenate sulfides, phosphosulfurized terpenes, sulfurized esters, aromatic amines, diphenyl amines, alkylated dipheny
  • Hindered phenols include but are not limited to 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4- ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butyl phenol, 4-butyl-2,6-di-tert- butylphenol 2,6-di-tert-butylphenol, 4-pentyl-2-6-di-tert-butylphenol, 4-hexyl-2,6-di-tert- butylphenol, 4-heptyl-2,6-di-tert-butylphenol, 4-(2-ethylhexyl)-2,6-di-tert-butylphenol, 4- octyl-2,6-di-tert-butylphenol, 4-nonyl-2,6-di-tert-butylphenol, 4-decyl-2,6-d
  • an ashless antioxidant is a hindered, ester-substituted phenol, which can be prepared by heating a 2,6- dialkylphenol with an acrylate ester under based conditions, such as aqueous KOH.
  • Ashless antioxidants may be used alone or in combination.
  • the antioxidants are typically present in the range of about 0 wt % to about 95 wt %, in one embodiment in the range from about 0.01 wt % to 95 wt % and in another embodiment in the range from about 1 wt % to about 70 wt % and in another embodiment in the range from about 5 wt % to about 60 wt % based on the total weight of the lubricant composition.
  • the extreme pressure/anti-wear agents include a sulfur or chlorosulphur extreme pressure (EP) agent, a chlorinated hydrocarbon EP agent, or a phosphorus EP agent, or mixtures thereof.
  • EP agents are amine salts of phosphorus acid, chlorinated wax, organic sulfides and polysulfides, such as benzyldisulfide, bis-(chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized sperm oil, sulfurized methyl ester of oleic acid sulfurized alkylphenol, sulfurized dipentene, sulfurized terpene, and sulfurized Diels-Alder adducts; phosphosulfurized hydrocarbons, such as the reaction product of phosphorus sulfide with turpentine or methyl oleate, phosphorus esters such as the dihydrocarbon and trihydrocarbon phosphate, i.e., dibutyl phosphate, dihepty
  • the antiwear agent/extreme pressure agent comprises an amine salt of a phosphorus ester acid.
  • the amine salt of a phosphorus ester acid includes phosphoric acid esters and salts thereof; dialkyldithiophosphoric acid esters and salts thereof; phosphites; and phosphorus-containing carboxylic esters, ethers, and amides; and mixtures thereof.
  • the phosphorus compound further comprises a sulfur atom in the molecule.
  • the amine salt of the phosphorus compound is ashless, i.e., metal-free (prior to being mixed with other components).
  • the amines which may be suitable for use as the amine salt include primary amines, secondary amines, tertiary amines, and mixtures thereof.
  • Antifoam agents include organic silicones such as poly dimethyl siloxane, poly ethyl siloxane, polydiethyl siloxane, polyacrylates and polymethacrylates, trimethyl-triflouro-propylmethyl siloxane and the like.
  • An antifoam agent may be used in the range of about 0 wt % to about 20 wt %, in one embodiment in the range of about 0.02 wt % to about 10 wt % and in another embodiment in the range of 0.05 wt % to about 2.5 wt % based on the weight of the lubricant composition.
  • the viscosity modifier provides both viscosity improving properties and dispersant properties.
  • dispersant-viscosity modifiers include vinyl pyridine, N-vinyl pyrrolidone and ⁇ , ⁇ '-dimethylaminoethyl methacrylate are examples of nitrogen-containing monomers and the like.
  • Polyacrylates obtained from the polymerization or copolymerization of one or more alkyl acrylates also are useful as viscosity modifiers.
  • Functionalized polymers can also be used as viscosity modifiers. Among the common classes of such polymers are olefin copolymers and acrylate or methacrylate copolymers.
  • Functionalized olefin copolymers can be, for instance, interpolymers of ethylene and propylene which are grafted with an active monomer such as maleic anhydride and then derivatized with an alcohol or an amine. Other such copolymers are copolymers of ethylene and propylene which are reacted or grafted with nitrogen compounds.
  • Derivatives of polyacrylate esters are well known as dispersant viscosity index modifiers additives.
  • Dispersant acrylate or polymethacrylate viscosity modifiers such as Acryloid(TM) 985 or Viscoplex(TM) 6-054, from RohMax, are particularly useful.
  • Solid, oil- soluble polymers such as the PIB (polyisobutylene), methacrylate, polyalkystyrene, ethylene/propylene and ethylene/propylene/ 1 ,4-hexadiene polymers and maleic anhydride- styrene interpolymer and derivatives thereof, can also be used as viscosity index improvers.
  • the viscosity modifiers are known and commercially available.
  • the viscosity modifiers are preferably present in the range of about 0 wt % to 80 wt %, in one embodiment in the range from about 0.25 wt % to about 50 wt % and in another embodiment in the range from about 0.5 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • a suitable friction modifier may preferably be an organo-molybdenum compound, including molybdenum dithiocarbamate.
  • the friction modifier is a phosphate ester or salt including a monohydrocarbyl, dihydrocarbyl or a trihydrocarbyl phosphate, wherein each hydrocarbyl group is saturated.
  • Each hydrocarbyl group may contain from about 8 to about 30, or from about 12 up to about 28, or from about 14 up to about 24, or from about 14 up to about 18 carbons atoms.
  • the hydrocarbyl groups are alkyl groups. Examples of hydrocarbyl groups include tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl groups and mixtures thereof.
  • the friction modifier is a phosphate salt
  • the phosphate salt may for example be prepared by reacting an acidic phosphate ester with an amine compound or a metallic base to form an amine or a metal salt.
  • the amines may be monoamines or polyamines.
  • the friction modifier is a phosphite and may be a monohydrocarbyl, dihydrocarbyl or a trihydrocarbyl phosphite, wherein each hydrocarbyl group is saturated.
  • each hydrocarbyl group may independently contain from about 8 to about 30, or from about 12 up to about 28, or from about 14 up to about 24, or from about 14 up to about 18 carbons atoms.
  • the hydrocarbyl groups are alkyl groups. Examples of hydrocarbyl groups include tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl groups and mixtures thereof.
  • the friction modifier is a fatty imidazoline comprising fatty substituents containing from 8 to about 30, or from about 12 to about 24 carbon atoms.
  • a suitable fatty imidazoline includes those described in U.S. Pat. No. 6,482,777.
  • the friction modifiers can be used alone or in combination.
  • the friction reducing agents are preferably present in the range of about 0 wt % to 60 wt %, or from about 0.25 wt % to about 40 wt %, or from about 0.5 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • the anti-misting agents can be used alone or in combination.
  • the anti- misting agents are present in the range of about 0 wt % to 10 wt %, or from about 0.25 wt % to about 10 wt %, or from about 0.5 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • the corrosion inhibitors that can be used according to the invention include alkylated succinic acids and anhydrides derivatives thereof, organo phosphonates and the like.
  • the corrosion inhibitors may be used alone or in combination.
  • the rust inhibitors are present in the range of about 0 wt % to about 20 wt %, and in one embodiment in the range from about 0.0005 wt % to about 10 wt % and in another embodiment in the range from about 0.0025 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • Ashless metal deactivators include derivatives of benzotriazoles such as tolyltriazole, N,N- bis(heptyl)-ar-methyl- 1 H-benzotriazo le- 1 -methanamine, N,N-bis(nonyl)-ar-methyl- 1 H-
  • Benzotriazole- 1 -methanamine N,N-bis(decyl)ar-methyl- 1 H-Benzotriazole- 1 -methanamine, N,N-(undecyl)ar-methyl- 1 H-benzotriazo le- 1 -methanamine, N,N-bis(dodecyl)ar-methyl- 1 H- Benzotriazole- 1 -methanamine N,N-bis(2-ethylhexyl)-ar-methyl- 1 H-Benzotriazole- 1 - methanamine and mixtures thereof.
  • the metal deactivator is N,N-bis(l- ethylhexyl)ar-methyl-lH-benzotriazole-l -methanamine; 1,2,4-triazoles, benzimidazoles, 2- alkyldithiobenzimidazoles; 2-alkyldithiobenzothiazoles; 2-N,N-dialkyldithio- carbamoyl)benzothiazoles; 2,5-bis(alkyl-dithio)-l,3,4-thiadiazoles such as 2,5-bis(tert- octyldithio)-l,3,4-thiadiazole 2,5-bis(tert-nonyldithio)-l,3,4-thiadiazole, 2,5-bis(tert- decyldithio)-l,3,4-thiadiazole, 2,5-bis(tert-undecyldithio)-l,3,4-thiadiazole
  • the ashless metal deactivators may be used alone or in combination.
  • the ashless metal deactivators are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • Demulsifiers usable in a lubricant composition of the invention include polyethylene and polypropylene oxide copolymers and the like.
  • the demulsifiers may be used alone or in combination.
  • the demulsifiers are preferably present in the range of about 0 wt % to about 20 wt %, or from about 0.0005 wt % to about 10 wt %, or from about 0.0025 wt % to about 2.5 wt % based on the total weight of the lubricant composition.
  • Said lubricity aids include glycerol mono oleate, sorbitan mono oleate and the like.
  • the lubricity aids may be used alone or in combination.
  • the lubricity aids are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 10 wt % based on the total weight of the lubricant composition.
  • the flow improvers mentioned in the context of the lubricant composition of the invention include ethylene vinyl acetate copolymers and the like.
  • the flow improvers may be used alone or in combination.
  • the flow improvers are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • Said cloud point depressants include alkylphenols and derivatives thereof, ethylene vinyl acetate copolymers and the like.
  • the cloud point depressants may be used alone or in combination.
  • the cloud point depressants are preferably present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025% to about 5 wt % based on the total weight of the lubricant composition.
  • the pour point depressants include alkylphenols and derivatives thereof, ethylene vinyl acetate copolymers and the like. The pour point depressant may be used alone or in combination.
  • the pour point depressant are for example present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • the seal swell agents include organo sulfur compounds such as thiophene, 3- (decyloxy)tetrahydro- 1,1 -dioxide, phthalates and the like.
  • the seal swell agents may be used alone or in combination.
  • the seal swell agents are for example present in the range of about 0 wt % to about 50 wt %, or from about 0.0005 wt % to about 25 wt %, or from about 0.0025 wt % to about 5 wt % based on the total weight of the lubricant composition.
  • the lubricant composition according to the invention comprises in a preferred embodiment a further lubricant
  • said further lubricant may be selected from the group consisting of an ester, canola oil, castor oil, palm oil, sunflower seed oil, rapeseed oil, Tall oil, lanolin, polyalpha-olefin (PAO), polyalkylene glycol (PAG), a phosphate ester, an alkylated naphthalene (AN), a silicate ester, an ionic fluid and a lubricant with a pour point as measured by DIN ISO 3016(10/82) of below 0°C.
  • PAO polyalpha-olefin
  • PAG polyalkylene glycol
  • AN alkylated naphthalene
  • silicate ester an ionic fluid
  • the invention provides an ester with at least four (and preferably between 4 and 6) ester groups obtainable by reacting
  • said polyol alkoxylate and said monocarboxylic acid are as defined above for the lubricant composition of the invention.
  • Said ester with at least four ester groups is not cross- linked.
  • said tertraester is obtainable by reacting (a) a polyol comprising at least four hydroxyl groups with (b) a C8-C20 monocarboxylic acid and preferably with Oleic acid, whereby said polyol is alkoxylated with at least 5 propoxyl groups.
  • said ester with at least four ester groups is based on a polyol alkoxylate having the following structure:
  • a+b+c+d between 4 and 10 (e.g. 4, 5, 6, 7, 8, 9 or 10) and most preferably 5.
  • ester with at least four ester groups of the invention is obtainable by reacting (a) a polyol comprising at least four hydroxyl groups with (b) a saturated C8-C10 monocarboxylic acid (e.g. octanoic acid, nonanoic acid or decanoic acid) or with an unsaturated C16-C18 monocarboxylic acid (e.g. palmitoleic acid, sapienic acid, oleic acid or elaidic acid).
  • a polyol comprising at least four hydroxyl groups
  • a saturated C8-C10 monocarboxylic acid e.g. octanoic acid, nonanoic acid or decanoic acid
  • an unsaturated C16-C18 monocarboxylic acid e.g. palmitoleic acid, sapienic acid, oleic acid or elaidic acid.
  • said polyol has the structure shown above.
  • the invention provides a tetraester obtainable by reacting
  • polyol alkoxylate and said monocarboxylic acid are as defined above for the lubricant composition of the invention. Said tetraester is not cross-linked.
  • said tertraester is obtainable by reacting (a) a polyol comprising at least four hydroxyl groups with (b) a C8-C20 monocarboxylic acid and preferably with Oleic acid, whereby said polyol is alkoxylated with at least 5 propoxyl groups.
  • said tetraester is based on a olyol alkoxylate having the following structure:
  • a+b+c+d between 4 and 10 (e.g. 4, 5, 6, 7, 8, 9 or 10) and most preferably 5.
  • the tetraester of the invention is obtainable by reacting (a) a polyol comprising at least four hydroxyl groups with (b) a saturated C8-C10 monocarboxylic acid (e.g. octanoic acid, nonanoic acid or decanoic acid) or with an unsaturated C16-C18 monocarboxylic acid (e.g. palmitoleic acid, sapienic acid, oleic acid or elaidic acid).
  • a saturated C8-C10 monocarboxylic acid e.g. octanoic acid, nonanoic acid or decanoic acid
  • an unsaturated C16-C18 monocarboxylic acid e.g. palmitoleic acid, sapienic acid, oleic acid or elaidic acid.
  • said polyol has the structure shown above.
  • a further aspect of the invention concerns the use of an ester according to the invention as defined herein as a lubricant, wherein the lubricant is preferably selected from the group consisting of engine oil, oil drilling fluid, hydraulic oil, compressor oil, gear oil, bearing oil, low temperature lubricant and turbine oil.
  • the inventive ester and/or lubricant composition is used as low temperature lubricant for working temperatures of below 10°C, preferably of below 0°C and most preferably of below -30°C.
  • the ester is a tetraester of the invention as defined herein for lubrication at below 10°C, preferably of below 0°C and most preferably of below -30°C.
  • the polyol on which the tertraester is based can have the following structure:
  • a+b+c+d between 4 and 10 (e.g. 4, 5, 6, 7, 8, 9 or 10) and most preferably 5.
  • the invention concerns a lubricated item covered at least partially with the ester of the invention, wherein said lubricated item is selected from the group consisting of a ball bearing, a drill pipe, a drill bit and a gear mechanism (e.g. a step-up gear), an internal combustion engine, a gas engine, a stationary engine, a diesel engine, a marine diesel engine, a generator, a hydraulic system, a transmission system (e.g. automatic or manual transmission system), a differential, a gear box, an axle, a pump and a suspension system.
  • a gear mechanism e.g. a step-up gear
  • an internal combustion engine e.g. a gas engine, a stationary engine, a diesel engine, a marine diesel engine, a generator, a hydraulic system, a transmission system (e.g. automatic or manual transmission system), a differential, a gear box, an axle, a pump and a suspension system.
  • ester and the composition of the invention have a low toxicity of EC50 > 1000 as measured after 72 h according to DIN EN ISO 10253:2006.
  • pentaerythritol or propoxylated pentaerythritol was used as polyol either pentaerythritol or propoxylated pentaerythritol was used.
  • the propoxylated pentaerythritol used in the examples below (“Pentaerythritol + 5 PO") can be made by reacting about 5 equivalents of propylene oxide with 1 equivalent of pentaerythritol in the presence of a potassium catalyst. Upon completion of the reaction the potassium catalyst can be removed e.g. by treatment with magnesium silicate as is known in the art.
  • the polyol (either propoxylated or not as mentioned) is combined with a molar excess of the respective carboxylic acid (e.g. saturated C 8-10 monocarboxylic acid or oleic acid) and tin (II) oxalate as catalyst.
  • carboxylic acid e.g. saturated C 8-10 monocarboxylic acid or oleic acid
  • tin (II) oxalate e.g. saturated C 8-10 monocarboxylic acid or oleic acid
  • the catalyst can be removed by washing the reaction product five times with an equal volume of water, heating the washed product with magnesium silicate (5% by weight) for 2 hours at 90°C, and filtering.
  • the filtered product can further be steam stripped e.g. under 10 mm Hg pressure until the residual acidity is less than 1 mg KOH/gram.
  • biodegradation rate was measured using a manometric respirometry test according to OECD-Guideline 301 F adopted 17.07.92. The test was performed at a temperature of 22 ⁇ 2 °C under aerobic conditions in closed bottles with automatic data registration. Respirometric BOD-determination is carried out with C02-absorption on soda lime. For the puropose of the data outlined in the following, bio degradability is expressed as the percentage oxygen uptake (corrected for blank uptake) of the Chemical Oxygen Demand (COD).
  • COD Chemical Oxygen Demand
  • the pour point of a liquid is the lowest temperature at which it becomes semi solid and loses its flow characteristics. It was determined according to DIN ISO 3016(10/82). Lubricant quality is preferably determined using a testing under boundary lubricating conditions with the Brugger lubricant tester according to DIN 51347-1 at room temperature (20°C).
  • PO indicates the number of propoxyl groups on the pentaerythritol.
  • inventive esters shown above are based on pentaerythritol comprising on average five propoxyl groups.
  • “Skeletonema costatum” refers to water quality measured after adding the indicated amount of the ester. The water quality is measured by determining marine algal growth inhibition according to DIN EN ISO 10253:2006. A value of above 1000 indicates a sufficiently low toxicity. According to the above outlined results the alkoxylated polyol ester shows unexpected and enhanced lubrication properties and improved cold temperature behaviors. Furthermore it was surprising that despite the presence of propoxyl groups, the compound showed no disadvantages in toxicity and an improved biodegradability.

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Abstract

La présente invention concerne une composition lubrifiante comprenant un ester éventuellement réticulé pouvant être obtenu par la réaction d'un alcoxylate de polyol avec un acide monocarboxylique. D'autres aspects de l'invention concernent un tétraester pouvant être obtenu par la réaction d'un alcoxylate de polyol avec un acide monocarboxylique et les utilisations de ladite composition et dudit tétraester.
PCT/EP2013/053214 2013-02-18 2013-02-18 Lubrifiant d'ester destiné à des applications de lubrifiant de champ pétrolier et d'autres d'applications de lubrifiant industriel WO2014124698A1 (fr)

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CN107557124A (zh) * 2017-09-08 2018-01-09 肇庆高新区恒泰信息服务有限公司 一种螺杆式冷冻机滑动轴承用润滑剂及其制备工艺
CN107603703A (zh) * 2017-09-15 2018-01-19 浙江车路科技有限公司 耐磨抗极压机油添加剂及其制备方法
CN108546585A (zh) * 2015-11-01 2018-09-18 陈玉玲 一种润滑油的制备方法
CN108929760A (zh) * 2018-08-01 2018-12-04 苏州力森克液压设备有限公司 一种用于液压缸的复合型润滑剂
CN109233963A (zh) * 2018-10-30 2019-01-18 新疆金雪驰科技股份有限公司 一种超低温地铁专用齿轮油及其制备方法
CN109536238A (zh) * 2018-11-06 2019-03-29 苏州玖城润滑油有限公司 一种耐高温齿轮润滑脂
WO2019126923A1 (fr) 2017-12-25 2019-07-04 Dow Global Technologies Llc Polyalkylène glycols liposolubles modifiés
WO2019236446A1 (fr) 2018-06-04 2019-12-12 Tetramer Technologies, Llc Huiles de base lubrifiantes à partir de polyols alcoxylés estérifiés à l'aide d'acides gras saturés à longue chaîne
CN111018713A (zh) * 2019-12-19 2020-04-17 联泓(江苏)新材料研究院有限公司 一种季戊四醇环氧改性蓖麻油封端的聚合物及其制备方法和应用
CN111592648A (zh) * 2020-04-30 2020-08-28 佳化化学（茂名）有限公司 一种季戊四醇聚氧乙烯醚硬脂酸酯的合成方法
CN112210408A (zh) * 2020-09-28 2021-01-12 沈阳工业大学 具有低温流动性的脂肪酸酯类柴油抗磨剂及制备方法
CN112920873A (zh) * 2021-01-26 2021-06-08 宝鸡文理学院 一种基于天然产物的合成酯类润滑油基础油
WO2022125081A1 (fr) 2020-12-09 2022-06-16 Tetramer Technologies, Llc Lubrifiant biodégradable présentant une stabilité hydrolytique adaptée et une stabilité thermique améliorée par le biais d'une alkoxylation de glycérol
CN115052960A (zh) * 2019-12-13 2022-09-13 道达尔能源一技术公司 用于限制摩擦的润滑剂组合物
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