EP0471266B1 - Utilisation des oligomères ou des co-oligomères, respectivement obtenus à partir d'esters (méth)acrylates et de 1-alcènes en tant que huiles synthétiques - Google Patents

Utilisation des oligomères ou des co-oligomères, respectivement obtenus à partir d'esters (méth)acrylates et de 1-alcènes en tant que huiles synthétiques Download PDF

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EP0471266B1
EP0471266B1 EP91113123A EP91113123A EP0471266B1 EP 0471266 B1 EP0471266 B1 EP 0471266B1 EP 91113123 A EP91113123 A EP 91113123A EP 91113123 A EP91113123 A EP 91113123A EP 0471266 B1 EP0471266 B1 EP 0471266B1
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degrees
carbon atoms
meth
weight
cooligomers
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EP0471266A1 (fr
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Claudia Dr. Beyer
Rüdiger Dr. Jelitte
Horst Dr. Pennewiss
Heinz Jost
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Roehm GmbH Darmstadt
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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
    • 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
    • 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
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • 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
    • C10M107/22—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
    • 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
    • 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
    • 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
    • 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
    • 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
    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2205/0206—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers 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
    • C10M2209/02—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
    • 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
    • C10M2209/02—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
    • 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
    • C10M2209/02—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
    • 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
    • C10M2209/02—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

Definitions

  • the invention relates to the use of cooligomers of (meth) acrylic acid esters and ⁇ -olefins as synthetic oils in tribology.
  • Polymers obtained from ⁇ -olefins of different origins and with different polymerization processes were of particular interest. This is how polymers of ⁇ -olefins with 8-12 C atoms come in, which are obtained, for example, by means of Ziegler catalysts or catalysts for ionic polymerization, meaning due to their good VI and pour point values. Mixtures of such ⁇ -olefin oligomers with ester oils are said to have a relatively good compatibility with rubber materials. Another advantage described is the better miscibility of the olefin oligomer / ester mixtures with polar additives compared to the pure components.
  • cooligomers or copolymers of ⁇ -olefins with (meth) acrylic acid esters as mineral oil additives have attracted the interest of technology.
  • the included ⁇ -olefin greatly improves the thermal stability of the additives.
  • US Pat. No. 4,419,106 describes oil preparations which contain a hydrocarbon oil and a portion of a pour point depressant consisting of a copolymer of approx. 10-90% by weight alkyl acrylate units containing 8-20 alkyl carbon atoms and 90- Have 10% by weight of ⁇ -monoolefin units with 12-40 carbon atoms per 100% by weight of copolymer with a molecular weight M w of 1,000-100,000.
  • the narrow molecular weight range achieved and the high uniformity of the products are emphasized.
  • US Pat. No. 4,009,195 describes an oligomerization process in which a wide variety of (meth) acrylic acid derivatives, such as, for example, C1-C4-alkyl esters, in proportions of 1-35% by weight in addition to (meth) acrylic acid esters of C8-C34- Alkanols in proportions of 1-45% by weight are added continuously and at the same time to a mixture of radical initiators and 10-90% by weight of a 1-alkene having 4-32 C atoms in such a way that what occurs essentially immediately molar ratio of acid derivatives to 1-alkene in the reaction mixture is kept relatively constant in the range 0.001 to 0.2, the addition being intended to take place at a temperature which does not impair the oligomerization.
  • Copolymers containing isocyanate groups in the molecular weight range 500-10,000 can be prepared by solution polymerization of C1-C20-alkyl esters of (meth) acrylic acid and olefins with 1-alkenyl isocyanate (cf. DE-A 32 45 298).
  • 4,526,950 describes a preparation process for copolymers in which, starting from at least one ⁇ -olefin having at least 6 C atoms and at least one unsaturated carboxylic acid or derivatives which are copolymerizable with the olefins, in the presence of a radical Initiator, the mixture of the components is heated to at least 135 degrees C in the absence of solvents or diluents, none of the reactive monomers being used in excess in order to avoid a dilution effect.
  • SU-A 1 135 752 copolymers of decyl methacrylate and tetradecene with a molecular weight of 8,000 - 13,000 are claimed as lubricating oil thickeners.
  • EP-A 217 602 discloses oil additives based on ethylene copolymers, inter alia with ethylenically unsaturated mono- or dicarboxylic acids or their esters, which have a molecular weight M n of ⁇ 1,000.
  • both classes of substances used have disadvantages. Due to their non-polar structure, the polyolefins show too little solubility when they are to be used together with polar components, for example high-pressure (EP) additives. Because of their polar structure, the esters are known to have serious disadvantages, such as problems with the miscibility with mineral oils, non-mineral oil-based base oils and poor seal compatibility. In addition, the ester function can give rise to hydrolysis, with the result that that the corrosion of metal parts is promoted. Attempts are made to compensate for the disadvantages mentioned by mixing hydrocarbons with esters, but this requires a considerable amount of development work in practice.
  • EP high-pressure
  • the synthetic oil mixtures used are to have dispersing activity for, for example, black sludge, it is necessary to add low or high molecular weight substances (for example "Ashless Dispersants" of the polyisobutenylsuccinimide type or VI improvers provided with polar groups). This means a considerable effort.
  • these mostly nitrogen-containing compounds can cause sealing problems.
  • the cooligomers CM used according to the invention contain component C), dispersing efficiency is achieved without the notorious problems which occur when using, for example, nitrogen-containing monomers, in particular seal incompatibility.
  • the components A), B) and C) in the cooligomers CM should be 100% complementary.
  • the cooligomers used according to the invention are by definition in the molecular weight range Mw 1,500 to 25,000 (determination by gel permeation chromatography, cf. HF Mark et al. Encyclopedia of Polymer Science & Technology Vol. 10, 1-19, J. Wiley 1987).
  • Examples of representatives of component A) include: Butene-1, Penten-1, Hexen-1, Hepten-1, Octen-1, Nonen-1, Decen-1, Undecen-1, Dodecen-1, Tridecen-1, Tetradecen-1, Pentadecen-1, Hexadecen- 1, Heptadecen-1, Octadecen-1, Nonadecen-1, Eicosen-1, Heneicosen-1, Docosen-1, Trocosen-1, Tetracosen-1, Pentacosen-1, Hexacosen-1, Heptacosen-1, Octacosen-1, Nonacosen-1, Triaconten-1, Hentriaconten-1, Dotriaconten-1, or the like. Also suitable are branched-chain alkenes, such as vinylcyclohexane, 3,3-dimethylbutene-1, 3-methylbutene-1, diisobutylene-4-methylpentene-1 or the
  • alkenes-1 having 10 to 32 carbon atoms which are obtained in the polymerization of ethylene, propylene or mixtures thereof, these materials in turn being obtained from hydrocracked materials.
  • component A) of the cooligomers CM stands for 1-decene, dodecene or for tetradecene is particularly preferred. Decen is very particularly preferred, when it is used the best low-temperature behavior (pour point) is registered.
  • cooligomers CM in which component B) consists of (meth) acrylic acid esters with 4 to 24, preferably 8 to 22, carbon atoms in the alkyl radical or mixtures thereof.
  • component B) consists of (meth) acrylic acid esters with 4 to 24, preferably 8 to 22, carbon atoms in the alkyl radical or mixtures thereof.
  • Examples include the monomers: Butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, isodecyl acrylate, decyl acrylate, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, Dodecylpentadecylacrylat, hexadecyl, Heptadecylacrylat, octadecyl acrylate, Cetylstearylacrylat, oleyl, Nonadecylacrylat, eicosyl acrylate
  • Cooligomeric CM of the type described are synthetic oil components of the prior art quite comparable in terms of characteristics such as viscosities, VI index, low-temperature behavior, evaporation and oxidation stability and other practical properties. However, they have the following advantages over the prior art described: Due to the combination of polar monomers with nonpolar, there are no problems with miscibility Mineral oils, poly- ⁇ -olefins (PAO), esters or other basic liquids as well as no solubility problems with additives. The sealing behavior is absolutely neutral. Corrosion due to acid formation can also be excluded.
  • oligomers are used as a synthetic oil component, which also contain component C) in a sufficient amount, there is good dispersing action, sealing problems being avoided due to the oxygen-containing dispersing group and there being no loss in the shear stability of the mixture, as occurs, for example, when using high molecular weight VI - Improvers occur.
  • Synthetic oils are understood to mean in particular the polyalphaolefins (PAO) preferred by technology and the organic esters (OE) such as dicarboxylic acid and polyol esters (cf. EI Williamson, J. Synth. Lubr. 2 (4) 329 - 341 (1986); 3 (1) 45 - 53 (1987); A. Plagge, Tribologie und Schmtechnikstechnik 34, 148 - 156 (1987); Ullmann, 4th edition, Vol. 20, loc. cit. pp. 514-821). Crack olefins primarily serve as starting materials for the polyalphaolefins, predominantly with a boiling point between 30 and 300 degrees C.
  • the polyalphaolefins generally correspond to the general formula III where R is an alkyl radical, in particular having 6-10 carbon atoms, with a molecular weight of usually 300-6000 ( M w).
  • Organic esters are, on the one hand, the esters of dicarboxylic acids with 3 to 17 carbon atoms, such as adipic acid, azelaic acid and sebacic acid with primary alcohols - the most important alcohol component in this case are polyalkylene glycols - on the other hand, the monocarboxylic acid esters, especially the esters of C6-C12 carboxylic acids with in particular branched alcohols, especially those with the neopentyl skeleton such as Neopentyl alcohol, trimethylol propane and pentaerythritol.
  • the ester 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 corrosive degradation products can occur.
  • the viscosities range from values around 5.9 [mm2 / s at 38 degrees C] for the neopentyl glycol ester of n-C7 acid to 16.2 for the corresponding ester of n-C12 acid, or from the value 12, 1 for the trimethylolpropane ester of n-C6 acid up to 36.4 for the corresponding ester of n-C12 acid.
  • the cooligomers of the claimed type can be prepared under certain conditions by radical-induced polymerization, for example by thermal polymerization and with the addition of a suitable initiator or a redox system.
  • the polymerization can be carried out in the absence of a solvent or in the presence of suitable solvents.
  • all conventional solvents identified as polymerization media can be used, as well as mineral oils, HC oils, PAO, esters or oligomers that have already been produced.
  • the 1-alkene according to component A) can be specified in a suitable reaction vessel and brought to a suitable reaction temperature. Generally, a temperature range from 80 to 200 degrees C, in particular 160 ⁇ 20 degrees C are considered to be a suitable range.
  • component B) or B) + C) is added in the proportions provided for this purpose in the same temperature range, preferably in the feed over a certain period, for example 0.25-10 hours, for example within 5 1/2 hours. It is advisable to allow the batch to polymerize for a while, usually a few hours - as a starting point, approx. 6 hours - It has proven advantageous to add the initiator throughout the reaction, for example in portions at about thirty minute intervals or continuously in accordance with Art an admission procedure.
  • Known radical initiators can be used as initiators (cf.Kirk-Othmer, 3rd Ed., Vol. 13, pg. 355 - 373, Wiley Interscience 1981; Rauch-Puntigam loc.cit.).
  • the total amount of initiator used is generally in the range 0.1-10% by weight, preferably in the range 0.1-5% by weight, based on the total of the monomers.
  • Initiators are expediently chosen whose decay characteristics are adapted to the polymerization modalities.
  • a guideline is a half-life of the initiator (in benzene) at the reaction temperature of approximately 0.25 hours.
  • These include, for example, peroxidic initiators such as di-tert-butyl peroxide.
  • the addition of 0.001-0.005 mol of initiator per portion should be given when adding in portions. According to the available results, there is an extensive conversion of the monomers, for example by 98%, so that in many cases there is no need to separate off the monomers or even further work up. If the requirements for the flash point are high, for example, the residual monomer must be removed.
  • the products generally are colorless, oily liquids that mix completely with mineral oil, PAO, HC oils and ester oils.
  • reaction temperature but 140 degrees C initiator used: tert-butyl perbenzoate
  • reaction temperature 140 degrees C initiator: tert-butyl perbenzoate 4.8% by weight.
  • reaction temperature 126 degrees C initiator: tert-butyl personoate 4.8% by weight.
  • Example 4 Carried out as in Example 4, but in addition to 1 mol of 1-decene in the initial charge, 280 g of synthetic oil prepared in accordance with Example 4 were used as the solvent.
  • methacrylate component is butyl methacrylate, feed time 3.5 hours.
  • PAO40 in PAO 6 Oligomer from Example 18 in PAO6 formulation 45% PAO 40 14.2% commercial DI package 40.8% PAO6 45% oligomer 14.2% commercial DI package 40.8 PAO6 ⁇ (100 degrees C) 19.5 mm2 / s 18.7 mm2 / s VI 147 148 SAE class 10W-50 10W-50 VW TD result 63.7 points, all rings free 67.2 points, all rings free

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (1)

  1. Utilisation en tribologie, en tant qu'huile de synthèse, de co-oligomères constitués par :
    A) 10 à 40 % en poids d'au moins un 1-alcène ayant 4 à 32 atomes de carbone par molécule,
    B) 40 à 90 % en poids d'au moins un (méth)acrylate de formule I
    Figure imgb0012
     dans laquelle R représente un atome d'hydrogène ou un groupe méthyle et R₁ est mis pour un groupe alkyle éventuellement ramifié ou un groupe cycloalkyle ayant 4 à 32 atomes de carbone dans le reste alkyle,
    C) 0 à 65, de préférence 5 à 40 % en poids d'un (méth)acrylate de formule II
    Figure imgb0013
     dans laquelle R' représente un atome d'hydrogène ou un groupe méthyle et R₂ est mis pour un groupe alkyle ayant 2 à 6 atomes de carbone, substitué par au moins un groupe hydroxyle, ou pour un reste
    Figure imgb0014
     dans lequel R₃ et R₄ représentent un atome d'hydrogène ou un groupe méthyle, R₅ est mis pour un atome d'hydrogène ou un groupe alkyle éventuellement ramifié ayant 1 à 40 atomes de carbone, et n représente un nombre entier qui vaut de 1 à 60, étant entendu que, lorsque n vaut 1, R₅ est mis pour un groupe alkyle éventuellement ramifié ayant 1 à 40 atomes de carbone,
    les co-oligomères présentant une masse moléculaire Mw comprise dans l'intervalle de 1500 à 25 000.
EP91113123A 1990-08-11 1991-08-05 Utilisation des oligomères ou des co-oligomères, respectivement obtenus à partir d'esters (méth)acrylates et de 1-alcènes en tant que huiles synthétiques Expired - Lifetime EP0471266B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4025494 1990-08-11
DE4025494A DE4025494A1 (de) 1990-08-11 1990-08-11 Syntheseoele, die ganz oder teilweise aus oligomeren bzw. cooligomeren von (meth)acrylsaeureestern und 1-alkenen bestehen

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EP0471266A1 EP0471266A1 (fr) 1992-02-19
EP0471266B1 true EP0471266B1 (fr) 1994-12-21

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EP (1) EP0471266B1 (fr)
AT (1) ATE115995T1 (fr)
DE (2) DE4025494A1 (fr)
DK (1) DK0471266T3 (fr)
ES (1) ES2068441T3 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4212569A1 (de) * 1992-04-15 1993-10-21 Roehm Gmbh Syntheseöle enthaltend Cooligomere, bestehend aus 1-Alkenen und (Meth)acrylsäureestern
DE4404620A1 (de) * 1994-02-14 1995-08-17 Roehm Gmbh Verbesserte Additive für Schmieröle
DE4427473A1 (de) 1994-08-03 1996-02-08 Roehm Gmbh Motorenöle mit hohem Dispergiervermögen und gutem Verschleißschutz
IT1270673B (it) * 1994-10-19 1997-05-07 Euron Spa Additivo multifunzionale per olii lubrificanti compatibili con fluoroelastomeri
DE19603696A1 (de) * 1996-02-02 1997-08-07 Roehm Gmbh Demulgatoren
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EP3880774B1 (fr) 2018-11-13 2022-07-13 Evonik Operations GmbH Procédé de préparation de copolymères aléatoires
PL3880773T3 (pl) 2018-11-13 2022-09-19 Evonik Operations Gmbh Kopolimery losowe do zastosowania jako oleje bazowe lub dodatki smarne
EP3907269B1 (fr) 2020-05-05 2023-05-03 Evonik Operations GmbH Copolymères à base de polydienes linéaire comme une huile de base ou un additif des compositions lubrifiantes
CA3184503A1 (fr) 2020-07-03 2022-01-06 Stefan Karl Maier Fluides de base a viscosite elevee a base de polyesters compatibles avec l'huile
WO2022003088A1 (fr) 2020-07-03 2022-01-06 Evonik Operations Gmbh Fluides de base à viscosité élevée à base de polyesters compatibles avec l'huile préparés à partir d'époxydes à longue chaîne
PL4015604T3 (pl) 2020-12-18 2023-05-08 Evonik Operations Gmbh Kopolimery akrylanowo-olefinowe jako płyny bazowe o wysokiej lepkości
CA3197881A1 (fr) 2022-05-24 2023-11-24 Evonik Operations Gmbh Copolymeres d'acrylate-olefine comme fluides de base de grande viscosite

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EP0471266A1 (fr) 1992-02-19
ES2068441T3 (es) 1995-04-16
DK0471266T3 (da) 1995-04-24
ATE115995T1 (de) 1995-01-15
DE4025494A1 (de) 1992-02-13
DE59103970D1 (de) 1995-02-02

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