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EP0566048A1 - Syntheseöle enthaltende Cooligomere, bestehend aus I-Alkenen und (Meth)-acrylsäureestern - Google Patents

Syntheseöle enthaltende Cooligomere, bestehend aus I-Alkenen und (Meth)-acrylsäureestern Download PDF

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Publication number
EP0566048A1
EP0566048A1 EP93105894A EP93105894A EP0566048A1 EP 0566048 A1 EP0566048 A1 EP 0566048A1 EP 93105894 A EP93105894 A EP 93105894A EP 93105894 A EP93105894 A EP 93105894A EP 0566048 A1 EP0566048 A1 EP 0566048A1
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EP
European Patent Office
Prior art keywords
carbon atoms
weight
meth
radical
cooligomers
Prior art date
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EP93105894A
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German (de)
English (en)
French (fr)
Inventor
Claudia Dr. Beyer
Rüdiger Dr. Jelitte
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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Publication of EP0566048A1 publication Critical patent/EP0566048A1/de
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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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
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    • 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
    • C10M107/22—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/28—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
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    • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
    • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C10M2209/0845—Acrylate; Methacrylate used as base material
    • C—CHEMISTRY; METALLURGY
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
    • C10M2209/0863—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid used as base material
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    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
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    • C10N2040/25—Internal-combustion engines
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary engines

Definitions

  • the invention relates to a method for lubricating machine components, synthetic oils with special properties being used, some of which are composed of cooligomers consisting of 1-alkenes and (meth) acrylic acid esters.
  • synthetic oils synthetic oils
  • synthetic oils are also used as hydraulic fluids (pressure transmission fluids).
  • synthetic oils have the following advantages over mineral oils, for example: high temperature stability, durability, good low-temperature flow behavior, high viscosity index (VI), low friction loss, low volatility (see Kirk-Othmer, vol. 12, pages 712 to 733 , J. Wiley, 1980).
  • the common synthetic oils belong to different classes of substances, in addition to polyethers, esters (of mono- and polybasic carboxylic acids with mono- and polybasic alcohols), phosphoric acid and phosphonic acid esters, silicones, silicate esters, polyhalohydrocarbons and fluorinated esters are polyolefins and alkyl aromatics.
  • polyethers esters (of mono- and polybasic carboxylic acids with mono- and polybasic alcohols), phosphoric acid and phosphonic acid esters, silicones, silicate esters, polyhalohydrocarbons and fluorinated esters are polyolefins and alkyl aromatics.
  • polymers with different proportions of ⁇ -olefins in particular ⁇ -olefins with 8 to 12 carbon atoms, which can be produced, for example, by means of Ziegler-Natta catalysis or ionic polymerization because of their good VI and pour point values.
  • 4,419,106 describes oil preparations which contain a hydrocarbon oil and a portion of a pour point depressant (pour point improver) consisting of a copolymer of about 10 to 90% by weight alkyl acrylate units containing 8 to 20 carbon atoms in the alkyl radical and 90 to 10% by weight ⁇ -olefin units with 12 to 40 carbon atoms with an average molecular weight M ⁇ w, as can be determined, for example, by gel permeation chromatography or by light scattering, from 103 to 105 daltons.
  • a pour point depressant pour point improver
  • Oligomeric VI improvers consisting of three monomer groups are described in US Pat. No. 3,968,148 and DE-A 22 43 064, respectively.
  • 4,009,195 describes an oligomerization process in which C1 to C4 alkyl esters of (meth) acrylic acid in proportions of 1 to 35% by weight in addition to (meth) acrylic acid esters of C8 to C34 alkanols in proportions of 1 to 45% by weight can be added continuously and simultaneously to a mixture of polymerization initiators and 10 to 90% by weight of a 1-alkene having 4 to 32 carbon atoms in such a way that the essentially immediately occurring molar ratio of acid derivatives to 1-alkene in the reaction mixture is kept relatively constant in the range between 10 ⁇ 3 and 0.2, the addition taking place at a temperature which does not impair the oligomerization.
  • copolymers are crosslinked, their pour point should be between 0 and -60 degrees C.
  • DE-A 32 45 298 describes copolymers with isocyanate groups in the molecular weight range from 500 to 104 daltons, which can be prepared by solution polymerization of C1 to C20 alkyl esters of (meth) acrylic acid, ⁇ -olefins with 1-alkenyl isocyanates. US Pat. No.
  • 4,526,950 describes a preparation process for copolymers in which, starting from at least one olefin having at least 6 carbon atoms and at least one unsaturated carboxylic acid or derivatives thereof, which can be copolymerized with the ⁇ -olefins, the mixture in the presence of a radical polymerization initiator is heated from the components in the absence of solvents or diluents to at least 135 degrees C, with none of the reactive monomers being used in excess in order to avoid a dilution effect. Furthermore, copolymers of decyl methacrylate and 1-tetradecene with a molecular weight between 8,000 and 13,000 daltons are claimed as lubricating oil thickeners in US Pat. No.
  • EP-A 217 602 discloses oil additives based on ethylene copolymers, for example with ethylenically unsaturated mono- or dicarboxylic acids or their esters, which have a molecular weight M n ⁇ 1,000 daltons.
  • No. 4,956,122 describes lubricating oil compositions which consist of polyalphaolefins (PAO), synthetic hydrocarbons, esters of carboxylic acids and possibly other additives.
  • PAO polyalphaolefins
  • the mixtures have good shear stability, good oxidation stability and good viscosity-temperature behavior and can be used as gear oil, engine oil and hydraulic oil formulations.
  • DE-A 40 25 494 describes synthetic oils containing, in addition to the usual constituents, 5 to 100% by weight of cooligomers which consist of 0 to 75% by weight of at least one 1-alkene having 4 to 32 carbon atoms in the molecule, 20 to 100% by weight.
  • (meth) acrylate / ⁇ -olefin oligomers are preferably used as mineral oil additives, with no technological connection with so-called "synthetic oils".
  • Prior art synthetic oils are usually made from hydrocarbons, e.g. Oligomers of 1-decene, and / or esters, for example dicarboxylic acid esters, are built up (see, for example, Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, vol. 20, pages 503 to 530, Verlag Chemie, 1981).
  • the cooligomers CM in proportions of 0 to 50% by weight of further (meth) acrylic acid esters of the formula II: contain in which R3 is hydrogen or methyl and R4 is an alkyl radical having 2 to 6 carbon atoms substituted by at least one hydroxyl group or a radical of the formula III: wherein R5 and R6 is hydrogen or methyl, R7 is hydrogen or an optionally branched alkyl radical having 1 to 40, preferably 1 to 20 carbon atoms and n is an integer from 1 to 60, with the proviso that if n is 1 stands, R7 stands exclusively for an optionally branched alkyl radical having 1 to 40 carbon atoms.
  • the average molecular weights Mw (weight average) of the cooligomers CM according to the invention are in the molecular weight range from 103 to 5 x 104 daltons, preferably between 1.5 x 103 and 2.5 x 104 daltons, particularly preferably between 1.5 x 103 and 2 x 104 daltons , (Determination of Mw by gel permeation chromatography, see HF Mark et. Al., Encyclopedia of Polymer Science and Technology. Vol. 10, pages 1 to 19, J. Wiley, 1987).
  • the components A), B) and optionally C) in the cooligomers CM should add up to 100% by weight.
  • component A) examples include: Octen-1, Nonen-1, Decen-1, Undecen-1, Dodecen-1, Tridecen-1, Tetradecen-1, or branched-chain alkenes such as vinylcyclohexane, 3,3-trimethyl-penten-1, 4,4, 5,5-tetramethyl-hexene-1 or the like. Also suitable are 1-alkenes having 10 to 14 carbon atoms which are obtained in the polymerization of ethylene, propylene or mixtures thereof, these starting materials in turn being obtained from hydrocracked materials.
  • component A) of the cooligomers CM stands for 1-decene, 1-dodecene or for 1-tetradecene is particularly preferred.
  • Component B) can consist, for example, of the following monomers: Butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, hexyl acrylate, heptyl acrylate, octyl acrylate, nonylacrylate, decyl acrylate, isodecyl acrylate, undecyl acrylate, Dodecyl acrylate, tridecyl acrylate, tetradecyl acrylate, pentadecyl acrylate, hexadecyl acrylate, heptadecyl acrylate, octadecyl acrylate, oleylacrylate, nonadecyl acrylate, eicosyl acrylate or the corresponding methacrylates.
  • alkyl methacrylates with 10 to 22 carbon atoms in the alkyl radical with a higher iso content.
  • Examples of representatives of component C possibly contained in Cooligomer C include those with an OH group in the alkyl radical, in particular those with the alkyl radical in position, for example the 2-hydroxyethyl methacrylate and the acrylate, the 3-hydroxypropyl methacrylate and acrylate, further the 2-hydroxypropyl methacrylate and acrylate, the mixtures of 2- and 3-hydroxypropyl methacrylates and acrylates, or the 4-hydroxybutyl methacrylate and the acrylate.
  • R4 represents a polyalkoxylated, in particular ethoxylated, radical, for example 2- (2-ethoxyethoxy) ethyl methacrylate and acrylate or (meth) acrylic acid esters of alcohols from ethoxylated C1- to C18- Fatty alcohol mixtures with average degrees of ethoxylation from 1 to 60, for example with an average degree of ethoxylation 11 or 25, starting from corresponding industrial products, such as Carbowax ® and Marlipal ® types, such as the methacrylic acid esters from Carbowax ® 550, Marlipal ® 1618/11, Marlipal ® 1618/25, Marlipal ® 013/200, Carbowax ® 2000 and Carbowax ® 750.
  • radical for example 2- (2-ethoxyethoxy) ethyl methacrylate and acrylate or (meth) acrylic acid esters of alcohols from ethoxylated C1- to C18- Fatty alcohol mixture
  • the cooligomers CM can be produced under certain conditions by radical-induced polymerization, for example by thermal polymerization or by adding a suitable initiator or a redox system.
  • the polymerization can take place either in the absence or in the presence of suitable solvents.
  • all conventional solvents identified as polymerization media can be used, as well as mineral oils, poly- ⁇ -olefins (PAO), ester oils or oligomers that have already been produced.
  • PAO poly- ⁇ -olefins
  • ester oils or oligomers that have already been produced.
  • the 1-alkene (component A)) can be specified in a suitable reaction vessel and brought to a suitable reaction temperature. In general, a temperature range from 80 to 200 degrees C, in particular from 120 to 180 degrees C, can be considered as a suitable range.
  • component B) or, if appropriate, components B) + C) are added in the proportions provided for this purpose in the same temperature range, preferably in the feed over a certain period of time, for example 0.25 to 10 hours. It is expedient to allow the batch to polymerize for some time, usually a few hours - 6 hours as a starting point. It has proven to be advantageous to add the polymerization initiator during the entire reaction, for example in portions at about thirty minute intervals or continuously in the manner of an addition process. Well-known initiators come Radical initiators in question (see Kirk-Othmer, Encyclopedia of Chemical Technology, 3rd Ed Ed. 12, pages 355 to 373, J. Wiley, 1981).
  • the total amount of initiator used is generally in the range from 0.1 to 10% by weight, preferably in the range from 0.1 to 5% by weight, based on the total of the monomers.
  • Initiators are expediently chosen whose decay characteristics are adapted to the polymerization modalities.
  • a half-life of the initiator (in benzene) at the reaction temperature of about 0.25 hours is mentioned.
  • peroxidic initiators such as di-tert-butyl peroxide.
  • the addition of 10 ⁇ 3 to 5 x 10 ⁇ 3 mol of initiator per portion should be given when adding in portions.
  • the oligomers CM are generally colorless, oily liquids which mix completely with mineral oils, PAO and ester oils.
  • PAO polyalphaolefins
  • OE organic esters
  • dicarboxylic acid and polyol esters are preferred by technology 45 to 53 (1987); A. Plagge, Tribologie und Schm michtechnik 34 , pages 148 to 156 (1987); Ullmann, 4th edition, Vol. 20., loc.cit, pages 514 to 821).
  • Starting materials for the PAO are primarily crack olefins, predominantly with a boiling point between 30 and 300 degrees C.
  • the PAO generally correspond to the general formula IV: wherein R represents an alkyl radical, in particular having 6 to 10 carbon atoms, with an average molecular weight of usually 3 x 102 to 6 x 103 daltons.
  • Organic esters (OE) are, on the one hand, the esters of dicarboxylic acids with 3 to 17 carbon atoms, such as adipic acid, azelaic acid or sebacic acid with primary alcohols, the most important alcohol components in this case being polyalkylene glycols, on the other hand the monocarboxylic acid esters, especially those Esters of C6 to C22 carboxylic acids with in particular branched alcohols, especially those with a neopentyl skeleton such as neopentyl alcohol, trimethylolpropane or pentaerythritol.
  • OE oils have a high adsorption capacity on metal surfaces and therefore good lubricity, but at the price of relative sensitivity to (hydrolytic) degradation, so that they are corrosive Degradation products can occur.
  • OE which are used as synthetic oil components, typically have kinematic viscosities of 2 to 500, preferably between 2 and 20 mm2 s ⁇ 1 at 100 degrees C.
  • the product is a colorless, oily liquid that is completely miscible with mineral oils, polyolefins or ester oils.
  • the dynamic viscosity ⁇ is measurable up to a content of cooligomers CM of 35% by weight in ester oil (trimethyladipic acid octyldecyl ester) regardless of Shear rate as shown in diagram 1 (measurement according to DIN 51 382 or ASTM-D 3945).
  • the low-temperature behavior of the synthetic oil according to the invention was determined in the "Cold Cranking Simulator" according to ASTM D 2602 and with a mixture of ester oil and polyalphaolefin (PAO 100: 1-decene oligomer with kinematic viscosity approx. 100 mm2 s ⁇ 1 at 100 degrees C) compared.
  • PAO 100 1-decene oligomer with kinematic viscosity approx. 100 mm2 s ⁇ 1 at 100 degrees C
  • the dynamic viscosity ⁇ at -25 degrees C of the synthetic oil according to the invention is approximately 45% lower than that of a comparable synthetic oil consisting of ester oil and PAO 100 (diagram 2).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
EP93105894A 1992-04-15 1993-04-09 Syntheseöle enthaltende Cooligomere, bestehend aus I-Alkenen und (Meth)-acrylsäureestern Withdrawn EP0566048A1 (de)

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DE4212569A DE4212569A1 (de) 1992-04-15 1992-04-15 Syntheseöle enthaltend Cooligomere, bestehend aus 1-Alkenen und (Meth)acrylsäureestern
DE4212569 1992-04-15

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0697457A1 (de) * 1994-08-03 1996-02-21 Röhm GmbH Motorenöle mit hohem Dispergiervermögen und gutem Verschleissschutz
US6432878B1 (en) 1999-01-15 2002-08-13 Cognis Corporation Adjuvant composition
WO2014065984A1 (en) * 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
EP2855645A1 (en) * 2012-06-04 2015-04-08 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
WO2020099079A1 (en) 2018-11-13 2020-05-22 Evonik Operations Gmbh Process for preparing random copolymers
WO2020099078A1 (en) 2018-11-13 2020-05-22 Evonik Operations Gmbh Random copolymers for use as base oils or lubricant additives
US11603425B2 (en) 2020-05-05 2023-03-14 Evonik Operations Gmbh Hydrogenated linear polydiene copolymers as base stock or lubricant additives for lubricant compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7648950B2 (en) * 2005-04-22 2010-01-19 Rohmax Additives Gmbh Use of a polyalkylmethacrylate polymer

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FR2162165A1 (ja) * 1971-12-02 1973-07-13 Sumitomo Chemical Co
US4956122A (en) * 1982-03-10 1990-09-11 Uniroyal Chemical Company, Inc. Lubricating composition
WO1990013620A1 (en) * 1989-05-01 1990-11-15 Mobil Oil Corporation Novel vi enhancing compositions and newtonian lube blends
WO1991001362A1 (de) * 1989-07-21 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Additiv zur beeinflussung der rheologie von ölen und fetten, seine herstellung und seine verwendung
EP0471266A1 (de) * 1990-08-11 1992-02-19 Röhm Gmbh Verwendung von Oligomeren bzw. Cooligomeren von (Meth)acrylsäureestern und 1-Alkenen als Syntheseöle
EP0418610B1 (de) * 1989-09-09 1994-01-19 Röhm Gmbh Dispergierwirksame Viskositäts-Index-Verbesserer

Patent Citations (6)

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Publication number Priority date Publication date Assignee Title
FR2162165A1 (ja) * 1971-12-02 1973-07-13 Sumitomo Chemical Co
US4956122A (en) * 1982-03-10 1990-09-11 Uniroyal Chemical Company, Inc. Lubricating composition
WO1990013620A1 (en) * 1989-05-01 1990-11-15 Mobil Oil Corporation Novel vi enhancing compositions and newtonian lube blends
WO1991001362A1 (de) * 1989-07-21 1991-02-07 Henkel Kommanditgesellschaft Auf Aktien Additiv zur beeinflussung der rheologie von ölen und fetten, seine herstellung und seine verwendung
EP0418610B1 (de) * 1989-09-09 1994-01-19 Röhm Gmbh Dispergierwirksame Viskositäts-Index-Verbesserer
EP0471266A1 (de) * 1990-08-11 1992-02-19 Röhm Gmbh Verwendung von Oligomeren bzw. Cooligomeren von (Meth)acrylsäureestern und 1-Alkenen als Syntheseöle

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0697457A1 (de) * 1994-08-03 1996-02-21 Röhm GmbH Motorenöle mit hohem Dispergiervermögen und gutem Verschleissschutz
US6432878B1 (en) 1999-01-15 2002-08-13 Cognis Corporation Adjuvant composition
EP2855645A1 (en) * 2012-06-04 2015-04-08 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
EP2855645B1 (en) * 2012-06-04 2019-08-14 Shell International Research Maatschappij B.V. Lubricating oil composition
WO2014065984A1 (en) * 2012-10-24 2014-05-01 Exxonmobil Reearch And Engineering Company High viscosity index lubricating oil base stock viscosity modifier combinations, and lubricating oils derived therefrom
WO2020099079A1 (en) 2018-11-13 2020-05-22 Evonik Operations Gmbh Process for preparing random copolymers
WO2020099078A1 (en) 2018-11-13 2020-05-22 Evonik Operations Gmbh Random copolymers for use as base oils or lubricant additives
CN113015780A (zh) * 2018-11-13 2021-06-22 赢创运营有限公司 制备无规共聚物的方法
US11453837B2 (en) 2018-11-13 2022-09-27 Evonik Operations Gmbh Random copolymers for use as base oils or lubricant additives
CN113015780B (zh) * 2018-11-13 2022-11-04 赢创运营有限公司 制备无规共聚物的方法
US11603425B2 (en) 2020-05-05 2023-03-14 Evonik Operations Gmbh Hydrogenated linear polydiene copolymers as base stock or lubricant additives for lubricant compositions

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Publication number Publication date
DE4212569A1 (de) 1993-10-21
JPH0641562A (ja) 1994-02-15

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