DE1520696A1 - Lubricating oil additives - Google Patents

Lubricating oil additives

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Publication number
DE1520696A1
DE1520696A1 DE19641520696 DE1520696A DE1520696A1 DE 1520696 A1 DE1520696 A1 DE 1520696A1 DE 19641520696 DE19641520696 DE 19641520696 DE 1520696 A DE1520696 A DE 1520696A DE 1520696 A1 DE1520696 A1 DE 1520696A1
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Germany
Prior art keywords
nitrogen atom
compounds
polymerized
methacrylic acid
vinyl
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Granted
Application number
DE19641520696
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German (de)
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DE1520696C (en
DE1520696B2 (en
Inventor
Koch Dr Ernst
Heinz Jost
Jochum Dr Nicolaus
Wilhelm Rosskopp
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Roehm and Haas GmbH
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Roehm and Haas GmbH
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Publication of DE1520696A1 publication Critical patent/DE1520696A1/en
Publication of DE1520696B2 publication Critical patent/DE1520696B2/en
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Publication of DE1520696C publication Critical patent/DE1520696C/en
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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
    • C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
    • C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • 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
    • 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
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • 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
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • 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
    • C10M2205/026—Butene
    • 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
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Description

Gegenstand der im nachstehenden beschriebenen Erfindung 1st ein Verfahren zur Herstellung von Schmierölzusätzen mit ausgezeichnetem Dispergiervermögen. FUr diesen Zweck 1st bereits eine große Reihe von Verbindungen vorgeschlagen, ohne daß bisher ein Produkt bekannt 1st, das allen Anforderungen hinsichtlich Wirksamkeit und Gestehimgekosten gerecht wird· Es ist bekannt« für den genannten Zweck brauchbare Produkte derart herzustellen» dafl polymerisierbar Verbindungen, deren Homopolymerisate in öl löslich sind, mit heterocyclischen Verbindungen mit einem tertiären Ringstickstoffatom, die eine polymerisierbar« Äthylendoppelbindung aufierhalb des Ringes« jedoch unmittelbar an diesem, aufweisen, mischpolyaierisiert werden. Als Beispiele für Monomere der eraXten Art selen vor allem Ester der Acrylsäure und Methacrylsäure, deren Alkoholrest mindestens 8, mit Vorteil 12 bis 16, C-Atome aufweist, ferner Vinylester organischer Säuren oder höhere Ester ungesättigter Dicarbonsäuren, wie Fumarsäure- und Itakonsäureester« genannt« - Monomere der zweiten Klasse Sind z· B, Vinylpyridine, Vinylpyrrolidine und Vinylpyrroll« done.The subject of the invention described below is a process for the production of lubricating oil additives with excellent Dispersibility. For this purpose is already proposed a large number of compounds without that so far a product is known that meets all requirements in terms of efficacy and cost of ownership, it is known that products that can be used for the stated purpose in this way to produce »that polymerisable compounds, their Homopolymers are soluble in oil, with heterocyclic Compounds with a tertiary ring nitrogen atom, the a polymerizable ethylene double bond on the outside Ring "but directly on this, have, mixed-polymerized will. As examples of monomers of the ancient kind selenium, especially esters of acrylic acid and methacrylic acid, the alcohol radical of which has at least 8, advantageously 12 to 16, carbon atoms has, furthermore vinyl esters of organic acids or higher esters of unsaturated dicarboxylic acids, such as fumaric acid and Itaconic acid esters "called" - monomers of the second class Are, for example, vinylpyridines, vinylpyrrolidines and vinylpyrroll « done.

Es 1st weiterhin bekannt, Schmierölzusätze derart herzustellen, daß das ein tertiäres Stickstoffatom aufweisende Monomere zu einem Zeltpunkt zu dem in Polymerisation beflndli-It is also known to produce lubricating oil additives in such a way that the monomer having a tertiary nitrogen atom has reached a point at which the polymer

i-i τί f"l (-* τ*1 (-^nii τί f "l (- * τ * 1 (- ^ n

chen Monomeren gegeben wird, in dem dieses bereits zu 40 bis 85 % polymerleiert 1st. Das Vorliegen von mindestens 15 %der Ausgangeverbindung in monomerer Form wird dabei als unerläßlich angesehen, da Pfropfpolymerisate, diechen monomers is given in which this is already polymerized to 40 to 85 % . The presence of at least 15 % of the starting compound in monomeric form is regarded as essential, since graft polymers that

909816/0676909816/0676

BAD ORIGINALBATH ORIGINAL

erhalten werden, wenn das stickstoffhaltig« Monomere in Gegenwart des auspolymsrlsierten Basisprodukt· polymerisiert wird, hinsichtlich Verträglichkeit und Stabilität einen schlechteren Effekt aufweisen als die gekennzeichne« ten und z. B. in der deutschen Auslegeschrift i 118 971 beschriebenen Produkte. Zu technisch besondere brauchbaren Schmierölzusätzen kommt man nach der genannten Druckschrift dann» wenn ein höherer Methacrylester innerhalb des bereits genannten Bereiches von 40 bis 85 % Umsatz polymerisiert wird* danach etwa δ Gew.-^ N-Vlnylpyrrolldon zugesetzt werden und das Ganze auspolymerislert wird.are obtained when the nitrogen-containing monomer is polymerized in the presence of the fully polymerized base product, have a worse effect in terms of compatibility and stability than the marked and z. B. in the German Auslegeschrift i 118 971 described products. According to the cited publication, technically particularly useful lubricating oil additives are obtained when a higher methacrylic ester is polymerized within the already mentioned range of 40 to 85% conversion * then about δ% by weight of N-vinylpyrrolldone is added and the whole is polymerized.

Es wurde gefunden« daß jenen Produkten, die bisher bereits als Schmierölzusätze, und zwar zur Verbesserung des VIskosltäts-Temperatur-Verhaltens und/oder zur Erniedrigung des Stockpunkte, vorgeschlagen worden sind, zusätzlich ein hohes Disperglervermögen verliehen werden kann, wenn polymerisierbar^ Verbindungen mit einem tertiären Stickstoffatom in Gegenwart solcher als Schmierölzusätze bereite bekannter Polymerisate bzw. Mischpolymerisate unter der Einwirkung radikaliseher Beschleuniger polymerisiert werden· Der angestrebte Effekt wird erreicht, wenn 2 bis 30 Gew.-# des pfropfend zu polymerisierenden, stickstoffhaltigen Monomeren, mit Vorteil 3 bis 4,5 Gew.-#, jeweils bezogen auf das Ausgangspolymerisat, zur Anwendung kommen· Mit besonderem Vorteil verwendet man dabei heterocyclische Stickstoffverbindungen, deren Stickstoffatom im Hing sitzt, während sich eine äthylenisch ungesättigte Gruppe außerhalb des Ringes, jedoch unmittelbar an diesem, befindet. Die Vorteile des neuen Verfahrens sind darin zu sehen, daß einmal alle bekannten VI-Verbeaserer hinsichtlich ihres Dispergiervermögens verbessert werden können und daß man zum anderen bei dem erfindungsgemäßen Vorgehen bei gleicher Wirksamkeit mit einen deutlich geringeren Anteil an stickstoffhaltigem Mononerem auskommt. Da die in der PraxisIt was found «that those products that have already been as lubricating oil additives, namely to improve the viscosity-temperature behavior and / or to reduce it of the pour points that have been proposed, additionally one high dispersing properties can be imparted if polymerizable compounds with a tertiary nitrogen atom are polymerized in the presence of such known polymers or copolymers, which are known as lubricating oil additives, under the action of radical accelerators. The desired effect is achieved when 2 to 30 wt .- # of the nitrogenous to be polymerized by grafting Monomers, with advantage 3 to 4.5 wt .- #, based in each case on the starting polymer are used · It is particularly advantageous to use heterocyclic nitrogen compounds whose nitrogen atom is in the ring, while an ethylenically unsaturated group is outside of the ring, but directly on it. the Advantages of the new method are to be seen in the fact that once all known VI verbeasers with regard to their Dispersibility can be improved and that one on the other hand in the procedure according to the invention with the same Effectiveness comes from a significantly lower proportion of nitrogen-containing monomers. Because in practice

S 0 9 8 1 6/0676 ' ' 'S 0 9 8 1 6/0676 '' '

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verwendeten stickstoffhaltigen, ungesättigten Verbindungen, z. B. N-Vinyl-2-pyrrolidon, erheblich teurer sind als die Monomeren des Basispolymerisats, z. B. Methaorylsäurelorolester, sind die Gestehungskosten für die neuen Produkte niedriger als bei der Herstellung gleichwertiger Produkte im Wege der Mischpolymerisation. Im Vergleich zu hinsichtlich der Bruttozusammensetzung gleichen Produkten, die erhalten werden, wenn z. B. N-Vinyl-2-pyrrolidon auf einen bis zu einem Umsatz von 40 bis 85 % polymerisieren Methacrylsäurelerolester pfropfend polymerisiert wird, weist ein erfindungsgemäß hergestelltes Produkt ein vornehmlich im Dieselmotor sieh bemerkbar raachendesWenmutztrageverraügea auf.nitrogen-containing unsaturated compounds used, e.g. B. N-vinyl-2-pyrrolidone, are considerably more expensive than the monomers of the base polymer, e.g. B. Methaorylsäurelorolester, the production costs for the new products are lower than for the production of equivalent products by means of copolymerization. Compared to the same in terms of the gross composition products obtained when e.g. B. N-vinyl-2-pyrrolidone polymerized to a conversion of 40 to 85% methacrylic acid elerol ester is polymerized by grafting, a product produced according to the invention has a noticeably smudging wear and tear mainly in diesel engines.

Wenn es auch möglich ist, das neue Verfahren derart auszuführen, das ein hinsichtlich seiner Dispergierwirkung zu verbesserndes Basispolymerisat als Block- oder Emulsionspolymerisat hergestellt und dieses, gegebenenfalls nach vorheriger mechanischer Zerkleinerung, in dem stickstoffhaltigen Monomeren verteilt wird, geht man in aller Hegel so vor, das man die Ausgangsverbindung als Löeungspolymerisat in Ul herstellt, nach beendeter Polymerisation das stickstoffhaltige Monomere zugibt und dieses unter der Einwirkung eines geeigneten Radikalbildner» pfropfend polymerleiert.Even if it is possible to carry out the new process in such a way that the one with respect to its dispersing effect Improving base polymer prepared as a block or emulsion polymer and this, if necessary after mechanical comminution beforehand, in which nitrogen-containing monomers are distributed, is generally accepted so before that one prepares the starting compound as a solution polymer in Ul, after the end of the polymerization adding nitrogen-containing monomers and polymerizing this under the action of a suitable radical former »grafting.

Als Baeispolymerisate kommen, wie bereits ausgeführt, die bisher als Sehmierölzusätze bekannten Produkte in Frage. Beispielhaft selen genannt; Polyacryl- und Polymethacrylsäureester, deren Alkoholrest mindestens S, mit Vorteil 12 bis 16, C-Atome aufweist, Polyisobutylen, Polyfumarsaureeater (C-Zahl im Alkoholrest 8 bis 18), Polyltakonate mit etwa den gleichen Alkoholresten, weiterhin Mischpolymerisate mit höheren Acryl-, Methacryl-, Furaar- und Itakonsäureestern untereinander oder mit Vinylacetat, ferner Mischpolymerisate der ebenAs already mentioned, the products previously known as Sehmieröl additives come into question as base polymers. Cited as an example selenium; Polyacrylic and polymethacrylic acid esters, the alcohol residue of which is at least S, advantageously 12 to 16, Has carbon atoms, polyisobutylene, polyfumaric acid ester (carbon number in the alcohol residue 8 to 18), Polyltakonate with about the same Alcohol residues, further copolymers with higher ones Acrylic, methacrylic, furaric and itaconic acid esters with one another or with vinyl acetate, as well as copolymers of the same

90 98 16/067 6 _ 4 _90 98 16/067 6 _ 4 _

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genannten Monomeren mit solchen Verbindungen* deren Homopolymerisate ölunlöRlich sind» wie Acryl- und Methacrylester mit einer C-Zahl von 1 bis 4 im Alkohelrestj der Mengenanteil* in dem die niederen Acryl- und Methaerylester am Aufbau der Mischpolymerisate beteiligt sein können, darf naturgemäß nur so groß sein« daß das erhaltene Mischpolymerisat öllös-Iicn bleibt. * Mit besonderem Vorteil werden als Comonoraere Aminoalkylester der Acryl- und Methacrylsäure, wie Dlraethylaminoäthylmethaerylat, Dlbutylaminoäthylacrylat, Dimethylaminobutylacrylat oder Butylamlnoäthylmethacrylat, verwendet·named monomers with such compounds * whose homopolymers are oil-insoluble »such as acrylic and methacrylic esters with a carbon number of 1 to 4 in the alcohol residuej the proportion * in which the lower acrylic and methaeryl esters in the structure of Copolymers can be involved, may of course only be so large that the copolymer obtained remains oil-soluble. * With particular advantage are called Comonoraere Aminoalkyl esters of acrylic and methacrylic acid, such as di-ethylaminoethyl methacrylate, di-butylaminoethyl acrylate, dimethylaminobutyl acrylate or butylaminoethyl methacrylate, are used

Als polymerislerbare Verbindungen mit einem tertiären Stickstoffatom sind N-Vlnyllactarne, wie N-Vinyl-2-pyrrolidon, N-Vlnylcaprolactäm, N-Vinylraethylpyrrolidon, N-Vinyl-5-plperldon, N-Vinyl-4-butylcaprolaotam und die entsprechenden Thiolactam· genannt. Weiterhin sind cyclische N-Vlnylimide, wie N-Vlnylsuceinimld, H-Vinyl-^-methylsucclnlisild undPolymerisable compounds with a tertiary nitrogen atom are N-vinyllactarns, such as N-vinyl-2-pyrrolidone, N-vinylcaprolactam, N-vinylraethylpyrrolidone, N-vinyl-5-plperldon, N-vinyl-4-butylcaprolactam and the corresponding thiolactam. Furthermore, cyclic N-vinylimides, such as N-vinylsuceinimld, H-vinyl - ^ - methylsuccinlisild and

K-Vlnylphthalimld, als Vertreter einer weiteren geeignetenK-vinylphthalimld, as a representative of another suitable

andereother

Stoffklasse genannt. Auch r·, heterocyclische Verbindungen, wie N-VinyloxaEolidone, sind als Verbindungen mit einem tertiären Stickstoffatom zur Durchführung des erfindungsgemäfien Verfahrene geeignet. - Aufler den eben genannten cyclischen Stickstoffverbindungen sind N-Vinylcarbonsäureanlde, wie N-Vinyl-N-äthylacetamld oder N-Vinyl-N-nethylbensanid, als Monomere im Sinne der vorliegenden Erfindung geeignet·Called substance class. Also r ·, heterocyclic compounds, such as N-VinyloxaEolidone, are available as compounds with a tertiary nitrogen atom to carry out the Processes according to the invention are suitable. - Aufler that one Cyclic nitrogen compounds mentioned are N-vinylcarboxylic acid systems, such as N-vinyl-N-ethylacetamide or N-vinyl-N-methylbenzanide, as monomers within the meaning of the present invention Invention suitable

Die Polymerisation kann unter der Einwirkung der für die zu polymerlslerenden Monomeren bekannten Radikalbildner durchgeführt werden, z. B. mit AzodlisobuttersMurenltrll und anderen Azoverbindungen, tert.-Butylperbenzoat oder tert·-Butylhydroperoxyd·The polymerization can take place under the action of the known free-radical formers are carried out to polymer-solubilizing monomers, e.g. B. with AzodlisobuttersMurenltrll and other azo compounds, tert-butyl perbenzoate or tert-butyl hydroperoxide

9098 16/067 6 - 5 -9098 16/067 6 - 5 -

BAD ORlGINAtBAD ORlGINAt

" «fill"« Fill

- 5 - ■- 5 - ■

Mit besonderem Vorteil wird die Polymerisation derart durchgeführt, dad der di« Polymerisation störende Luftsauerstoff weitgehend oder vollständig ausgeschlossen wird.The polymerization is carried out with particular advantage in such a way that because atmospheric oxygen interferes with the polymerization is largely or completely excluded.

Zu Produkten mit bevorzugter Wirksamkeit kommt man« wenn man die als verwendbare Coraonomere bereits genannten Aminoalkyl®» ter der Aoryl- und Methacrylsäure zusammen mit einem Monomeren mit mindestens einem tertiären Stickstoffatom auf ein Basiepolymeris&t, z. B· Polymethacrylaäurelorolester, pfropfend polymerisiert*Products with preferred efficacy are obtained “if the aminoalkyl® already mentioned as usable coraonomers » ter of aoryl and methacrylic acid together with one Monomers with at least one tertiary nitrogen atom a base polymer, e.g. B polymethacrylic acid lorol ester, polymerized by grafting *

Die naohstehenden Beispiele erläutern das erfindungsgemäße Verfahren, ohne den nachgesuchten Schutz auf eben diese Aueführtmgsformen zu beschränken. Gleichzeitig zeigen entsprechende Gegenüberstellungen den mit dem neuen Verfahren verbundenen technischen Fortschritt«The following examples illustrate the invention Procedure without restricting the protection sought to precisely these forms of execution. At the same time show appropriate Comparison of the technical progress associated with the new process "

9098 16/06 7 69098 16/06 7 6

-6--6-

SADORIGINALSADORIGINAL

Beispiel 1tExample 1t

96 Gewiohtsteile eines Mischpolymerisatβ aus 13 Gewiohtsteilen Methylraethaerylat und 65 Gewichteteilen tines Gemisches au* MethacrylsSiureestem von Fettalkoholen (mittlere C-Zahl 14) in ISO Gewichteteilen Mineralöl werden mit k Gewichteteilen N~Vinyl-2«pyrrolidon und C* S Gewichte teilen tert.-Butylperbenzoatlösung (50-^ig in Mrcethylphthalat) versetzt und unter Rühren und Luftaueachluß S Stunden bei 110° C polymerisiert · Nach einer Polyraerlsatienszeit von 1, 2 und J Stunden werden jeweils 0,1 Gewichtsteile tert.-Butylper-" benzoatlösims zusätzlich augegeben.96 parts by weight of a copolymer of 13 parts by weight of methyl methacrylate and 65 parts by weight of a mixture of methacrylic acid esters of fatty alcohols (mean carbon number 14) in ISO parts by weight of mineral oil are mixed with k parts by weight of N ~ vinyl-2 «pyrrolidone and C * S parts by weight of tert-butyl perbenzoate (50% in methyl phthalate) and polymerized with stirring and exclusion of air for 5 hours at 110 ° C. After a polyacrylate time of 1, 2 and J hours, 0.1 part by weight of tert-butyl per-benzoate solvent is added.

Beispielexample

Zu 92 Gewichtsteilen eines Mischpolymerisats aus 15 Gewichteteilen Methylmethacrylat und Sf> Gewichtsteilen eines Gemisches aus Methacrylsäureester!! von Pettalkeholen (mittlere C-Zahl 14) in 150 Gewichtsteilen Mineralöl werden 8 Gewichteteile N«Vinyl-2-pyrrolidon und 0^2 Gewichtsteile tert.-Butylperbenzoatlösung (50-^ig in DimethyIphthalat), letztere gelöst in 5 Gewichtateilen Mineralölβ gegeben· Da» Gemisch wird unter Rühren und Luftausschluß 8 Stunden bei 110° C polymerisiert. Nach 1,2 und J) Stunden Polymerisaticnsdauer werden jeweils 0,1 Gewichtateile der Peroxydlösung zusätzlich zugegeben. To 92 parts by weight of a copolymer of 15 parts by weight of methyl methacrylate and Sf> parts by weight of a mixture of methacrylic acid ester !! 8 parts by weight of N «vinyl-2-pyrrolidone and 0 ^ 2 parts by weight of tert.-butyl perbenzoate solution (50% in dimethyl phthalate), the latter dissolved in 5 parts by weight of mineral oil β, are added to Pettalkeholen (mean carbon number 14) in 150 parts by weight of mineral oil. The mixture is polymerized for 8 hours at 110 ° C. with stirring and with the exclusion of air. After 1.2 and 1) hours of polymerization, 0.1 parts by weight of the peroxide solution are additionally added.

Beispielexample

Zu 92 Gewichtsteilen eines Mischpolymerisats aus 15 Gewichtsteilen Methylmethaorylat und 85 Gewi eliteteilen eines Gemisches aus Methacrylsäureester» von Fettalkoholen (C-Zahl 12 - 18)To 92 parts by weight of a copolymer of 15 parts by weight of methyl methaorylate and 85 parts by weight of a mixture from methacrylic acid ester »from fatty alcohols (carbon number 12 - 18)

9 0 9 8 16/06769 0 9 8 16/0676

in 150 Gewiehtstellen Mineralöl werden 4 Gewiehteteile N-DinMtnylaminoäthylaethaerylat und 4 Gewicht*teile N-Vinyl· 2«pyrrolidon gegeben· Nach Zusatz von 0,2 Gewichtsteilen tert.-Butylperbensoatlösung (50-#ig in Dimethylphthalat) wixädas Gemisch unter starkem Rühren und Luftausechluß bei 110° C polyBierlsiert. Jeweils 0,1 Gewichteteile tert«- Butylperbenzoatlueung werden nach 1,2 und 5 Stunden zugegeben· Die Gesamtdauer beträgt 8 Stunden.In 150 weight points of mineral oil are 4 weight parts N-DinMtnylaminoäthylaethaerylat and 4 parts by weight * of N-Vinyl 2 «pyrrolidone given · After addition of 0.2 parts by weight tert.-butyl periglate solution (50% in dimethyl phthalate) wixädas mixture with vigorous stirring and exclusion of air PolyBerolised at 110 ° C. In each case 0.1 parts by weight tert «- Butyl perbenzoate solution is added after 1, 2 and 5 hours. The total time is 8 hours.

9 09 8 16/067 69 09 8 16/067 6

- 8—- 8th-

Motorische Prüfung von vinylpyrrolidonhaltlgen DispergiermittelnMotor testing of dispersants containing vinylpyrrolidone

Typ des AdditivesType of additive

% Additive im öl % Additives in the oil

MWM-Die*el-PrüflaufMWM-Die * el test run

Jolbenfeewertung (100 s= sauber)Jolbenfe rating (100 s = clean)

Dispergiervermögen It· Tafeltest gut bisDispersibility It · panel test good up

Opel-KaltlaufOpel cold run

(100 S= sauber) Bewertung für Sehlaro»- ablagerung nach h 135 h(100 S = clean) Rating for Sehlaro »- Deposition after h 135 h

Dispergierverasü gen It. Tüpfeltest gut bis "MDispersion gasification according to spot test good to "M

1.1.

2.2.

Polymerisat der Methacrylsäureester von Cocosfettalkoholen (mittlere C-Zahl im Al« koholrest 14,2) = ^MethaerylsäurelorolKter"Polymer of the methacrylic acid esters of coconut fatty alcohols (mean carbon number in the alcohol residue 14.2) = ^ MethaerylsäurelorolKter "

Mischpolymerisat aus 95#5 Gew·-^ Methacrylsäurelorolester und 4,5 Gew.-% VinylpyrrolidonCopolymer of 95 # 5 wt .- ^ methacrylic acid lorol ester and 4.5 wt .- % vinylpyrrolidone

Mischpolymerisat gemäß Beispiel 1 der vorliegenden Anmeldung (4 Gew. -% Vinylpyrrolidon)Copolymer according to Example 1 of the present application (4 wt -.% Vinyl pyrrolidone)

4. Misehpolym. aus 92 Methacrylsäurelorolester und 8 Gew.-^ VinylpyimL.4. Misehpolym. from 92 methacrylic acid lorolester and 8 wt .- ^ vinylpyimL.

5. Mischpolym. gen. Beisp. 2 der vorlieg. Anseidung (8 Gew.-^ Vlnylpyrrol.)5. mixed polymer. gen. Ex. 2 of the present. Isolation (8 wt .- ^ vinylpyrrole.)

3-63-6

etwa 55about 55

7474

72
7772
77

kein DPV < 50 hno DPV <50 h

> 50 h> 50 h

>50 h> 50 h

>50 h> 50 h

etwa 81about 81

8787

8888

8787

etwa 60about 60

8282

kein DPVno DPV

100 h100 h

>165 h> 165 h

>150 h >170 h> 150 h> 170 h

Die Durchführung dor in der vorstehenden Tabelle angegebenen Teste geschah auf folgende Weise:The implementation is given in the table above Testing was done in the following way:

+' "The Engine Testing of Crankcase Lubricating Oils", 1962, Seiten 53 bis 67 "Engine Testing and Evaluation ©f Crankcase Lubricants" von E. Kruppke + '"The Engine Testing of Crankcase Lubricating Oils", 1962, pages 53 to 67 "Engine Testing and Evaluation © f Crankcase Lubricants" by E. Kruppke

++' nThe Engine Testing ©f Crankcase Lubricating Oils", 1962, Seiten 1*3 bis 144 - E. Weise, BP Hamburg ++ ' n The Engine Testing © for Crankcase Lubricating Oils ", 1962, pages 1 * 3 to 1 44 - E. Weise, BP Hamburg

Alfense Sshiiiing, "Lea huiles pour moteure et le graissage des moteurs". Band 1, 1962, Seite 89.Alfense Sshiiiing, "Lea huiles pour moteure et le graissage des moteurs ". Volume 1, 1962, page 89.

90 98Ί 8/06 7 6 " l0 *90 98Ί 8/06 7 6 " l0 *

Claims (1)

PatentansprücheClaims 1» Verfahren zur Herstellung von Schmierölzusätzen mit hoher Dispergierwirkung» die aus einem ein öllösliches Homopolymerisat liefernden Monomeren oder aus mehreren solcher monomerer Verbindungen und aus pelymerisierbaren» ein tertiäres Stickstoffatom aufweisenden Monomeren,, gegebenenfalls aus weiteren ungesättigten Verbindungen» aufgebaut sind»1 »Process for the production of lubricating oil additives with a high dispersing effect» which are built up from a monomer which provides an oil-soluble homopolymer or from several such monomeric compounds and from polymerizable »monomers containing a tertiary nitrogen atom, optionally from further unsaturated compounds» » dadurch gekennzeichnet,characterized, daß in Gegenwart von als Vl-Verbesserer bekannten Polymerisaten bzw« Mischpolymerisaten ungesättigte Verbindungen mit einem tertiären Stickstoffatom radikalisch polymerisiert werden» wobei der Anteil dieser monomeren Verbindungen» bezogen auf das Polymerisat» 2 bis JO Oew.-# ausmacht.that in the presence of polymers or copolymers known as VI improvers with unsaturated compounds a tertiary nitrogen atom are radically polymerized »whereby the proportion of these monomeric compounds» based on the polymer is »2 to JO Oew .- #. 2. Verfahren nach Anspruch 1» dadurch gekennzeichnet» daß das Basispolymerisat aus höheren Acryl- oder Methacrylsäureestern mit mehr als 8, mit Vorteil 12 bis 16» C-Atomen im Alkoholrest» gegebenenfalls aus untergeordneten Mengen solcher monomerer Verbindungen» deren Homopolymerisate ulunltisllch sind» aufgebaut ist·2. The method according to claim 1 »characterized» that the Base polymer made from higher acrylic or methacrylic acid esters with more than 8, advantageously 12 to 16 »carbon atoms in the Alcohol residue »if necessary from minor amounts of such monomeric compounds» their homopolymers ulunltisllch are »is built up · 3. Verfahren nach den Ansprüchen 1 und 2» dadurch gekennzeichnet» daß als ein tertiäres Stickstoffatom aufweisende Monomere heterocyclische Verbindungen Verwendung finden» deren Stickstoff atom sich im Ring und deren äthylenisch ungesättigte Gruppe sich außerhalb des Ringes» jedoch unmittelbar an diesem» befindet.3. The method according to claims 1 and 2 »characterized» that as having a tertiary nitrogen atom Monomeric heterocyclic compounds are used »whose nitrogen atom is in the ring and whose ethylenically unsaturated group is outside the ring» but directly on it ». 4. Verfahren nach den Ansprüchen X und 2» dadurch gekennzeichnet» daß als drittes Comonomeres ein Aminoalkylester der4. The method according to claims X and 2 »characterized» that the third comonomer is an aminoalkyl ester 9098 16/067 69098 16/067 6 - 11 -- 11 - BAOORSGiNALBAOORSGiNAL 1R206961R20696 Acryl- oder Methacrylsäure in einer solchen Menge zur Anwendung kommt, daß die öllösiichkeit des Endprodukts erhalten bleibt·Acrylic or methacrylic acid is used in such an amount that the oil solubility of the end product is retained. 5« Verfahren* .-nach den Ansprüchen 1 bis kt dadurch gekennzeichnet ff daß sowohl die Herstellung des Basispolymerisats als auch die Pfropfpolymerisation in einem Lösungsmittel, vornehmlich in einem öl, erfolgen·5 «Process *.-According to claims 1 to k t characterized ff that both the preparation of the base polymer and the graft polymerization are carried out in a solvent, primarily in an oil. 6. Verfahren nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet« daß auf ein zum überwiegenden Teil aus einem höheren % Methacryleater (C-Zahl im Alkoholrest 12 bis 16) aufgebautes Polymerisat bzw. Mischpolymerisat N-Vinyl-2-pyrrolidon pfropfend polymerisiert wird·6. The method according to claims 1 to 5, characterized in 'that on a predominantly from a higher% Methacryleater constructed (number of carbon atoms in the alcohol residue 12 to 16) polymer or copolymer N-vinyl-2-pyrrolidone is polymerized pfropfend · 7* Verfahren nach Anspruch 6, dadurch gekennzeichnet, daß der Anteil an N-Vinyl-2-pyrrolidon 3 bis 4,5 Gew.-^, bezogen auf das Basispolymerisat, ausmacht.7 * Method according to claim 6, characterized in that the proportion of N-vinyl-2-pyrrolidone is 3 to 4.5 wt .- ^, based on the base polymer. 8, Verfahren nach den Ansprüchen 1 bis 7, dadurch gekennzeichnet, daß «usammen mit dem ein tertiäres Stickstoffatom aufweisenden Monomeren ein Aminoalkylester der Acryl- oder Methacrylsäure pfropfend polymerisiert wird· λ 8, The method of claims 1 to 7, characterized in that "ogether with a tertiary nitrogen atom-containing monomers an aminoalkyl esters of acrylic or methacrylic acid polymerized is pfropfend · λ 9 0 981670676 BAO ORIGINAL9 0 981670676 BAO ORIGINAL
DE19641520696 1964-06-06 1964-06-06 Process for the manufacture of lubricating oil additives Expired DE1520696C (en)

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DER0038086 1964-06-06

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2556080A1 (en) * 1974-12-12 1976-06-16 Erap HIGH QUALITY LUBRICANTS
US4243789A (en) * 1977-09-01 1981-01-06 The B. F. Goodrich Company Hydroxyl-containing liquid polymers and pressure-sensitive adhesives prepared therefrom
EP0691355A2 (en) 1994-07-04 1996-01-10 Röhm Gmbh Cooligomers and copolymers with dispersant activity
DE102007032120A1 (en) 2007-07-09 2009-01-15 Evonik Rohmax Additives Gmbh Use of comb polymer comprising polyolefin-based macro-monomer derived from repeating units and repeating units derived from low molecular monomers comprising e.g. styrene monomer, to reduce the fuel consumption in motor vehicles
DE102007046223A1 (en) 2007-09-26 2009-04-02 Evonik Rohmax Additives Gmbh Use of comb polymer comprising repeating units derived from polyolefin-based macro-monomer and repeating units derived from low molecular monomers comprising e.g. styrene monomer, to reduce fuel consumption in motor vehicles
WO2010102903A1 (en) 2009-03-10 2010-09-16 Evonik Rohmax Additives Gmbh Use of comb polymers as antifatigue additives
DE102010028195A1 (en) 2010-04-26 2011-10-27 Evonik Rohmax Additives Gmbh Lubricant for transmissions
WO2013182581A1 (en) 2012-06-06 2013-12-12 Evonik Oil Additives Gmbh Fuel efficient lubricating oils
US9080124B2 (en) 2004-07-16 2015-07-14 Evonik Rohmax Additives Gmbh Use of graft polymers
WO2018041755A1 (en) 2016-08-31 2018-03-08 Evonik Oil Additives Gmbh Comb polymers for improving noack evaporation loss of engine oil formulations
WO2018114673A1 (en) 2016-12-19 2018-06-28 Evonik Oil Additives Gmbh Lubricating oil composition comprising dispersant comb polymers
EP3450527A1 (en) 2017-09-04 2019-03-06 Evonik Oil Additives GmbH New viscosity index improvers with defined molecular weight distributions
WO2020064619A1 (en) 2018-09-24 2020-04-02 Evonik Operations Gmbh Use of trialkoxysilane-based compounds for lubricants
EP3708640A1 (en) 2019-03-11 2020-09-16 Evonik Operations GmbH Polyalkylmethacrylate viscosity index improvers
WO2020187954A1 (en) 2019-03-20 2020-09-24 Evonik Operations Gmbh Polyalkyl(meth)acrylates for improving fuel economy, dispersancy and deposits performance
WO2022129495A1 (en) 2020-12-18 2022-06-23 Evonik Operations Gmbh Process for preparing homo- and copolymers of alkyl (meth)acrylates with low residual monomer content
WO2023099637A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023099635A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023099634A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023110529A1 (en) 2021-12-17 2023-06-22 Evonik Operations Gmbh Hydraulic lubricant formulations with high flash point and improved shear stability
WO2024033156A1 (en) 2022-08-08 2024-02-15 Evonik Operations Gmbh Polyalkyl (meth)acrylate-based polymers with improved low temperature properties

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2556080A1 (en) * 1974-12-12 1976-06-16 Erap HIGH QUALITY LUBRICANTS
US4243789A (en) * 1977-09-01 1981-01-06 The B. F. Goodrich Company Hydroxyl-containing liquid polymers and pressure-sensitive adhesives prepared therefrom
EP0691355A2 (en) 1994-07-04 1996-01-10 Röhm Gmbh Cooligomers and copolymers with dispersant activity
US5712359A (en) * 1994-07-04 1998-01-27 Roehm Gmbh Chemische Fabrik Co-oligomers and copolymers having dispersant activity
US9080124B2 (en) 2004-07-16 2015-07-14 Evonik Rohmax Additives Gmbh Use of graft polymers
DE102007032120A1 (en) 2007-07-09 2009-01-15 Evonik Rohmax Additives Gmbh Use of comb polymer comprising polyolefin-based macro-monomer derived from repeating units and repeating units derived from low molecular monomers comprising e.g. styrene monomer, to reduce the fuel consumption in motor vehicles
DE102007046223A1 (en) 2007-09-26 2009-04-02 Evonik Rohmax Additives Gmbh Use of comb polymer comprising repeating units derived from polyolefin-based macro-monomer and repeating units derived from low molecular monomers comprising e.g. styrene monomer, to reduce fuel consumption in motor vehicles
WO2010102903A1 (en) 2009-03-10 2010-09-16 Evonik Rohmax Additives Gmbh Use of comb polymers as antifatigue additives
DE102009001446A1 (en) 2009-03-10 2010-09-23 Evonik Rohmax Additives Gmbh Use of comb polymers as antifatigue additives
DE102010028195A1 (en) 2010-04-26 2011-10-27 Evonik Rohmax Additives Gmbh Lubricant for transmissions
WO2011134695A1 (en) 2010-04-26 2011-11-03 Evonik Rohmax Additives Gmbh Transmission lubricant
WO2013182581A1 (en) 2012-06-06 2013-12-12 Evonik Oil Additives Gmbh Fuel efficient lubricating oils
WO2018041755A1 (en) 2016-08-31 2018-03-08 Evonik Oil Additives Gmbh Comb polymers for improving noack evaporation loss of engine oil formulations
US11015139B2 (en) 2016-08-31 2021-05-25 Evonik Operations Gmbh Comb polymers for improving Noack evaporation loss of engine oil formulations
WO2018114673A1 (en) 2016-12-19 2018-06-28 Evonik Oil Additives Gmbh Lubricating oil composition comprising dispersant comb polymers
US10731097B2 (en) 2017-09-04 2020-08-04 Evonik Operations Gmbh Viscosity index improvers with defined molecular weight distributions
EP3450527A1 (en) 2017-09-04 2019-03-06 Evonik Oil Additives GmbH New viscosity index improvers with defined molecular weight distributions
WO2020064619A1 (en) 2018-09-24 2020-04-02 Evonik Operations Gmbh Use of trialkoxysilane-based compounds for lubricants
EP3708640A1 (en) 2019-03-11 2020-09-16 Evonik Operations GmbH Polyalkylmethacrylate viscosity index improvers
WO2020187954A1 (en) 2019-03-20 2020-09-24 Evonik Operations Gmbh Polyalkyl(meth)acrylates for improving fuel economy, dispersancy and deposits performance
WO2022129495A1 (en) 2020-12-18 2022-06-23 Evonik Operations Gmbh Process for preparing homo- and copolymers of alkyl (meth)acrylates with low residual monomer content
WO2023099637A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023099635A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023099634A1 (en) 2021-12-03 2023-06-08 Totalenergies Onetech Lubricant compositions
WO2023110529A1 (en) 2021-12-17 2023-06-22 Evonik Operations Gmbh Hydraulic lubricant formulations with high flash point and improved shear stability
WO2024033156A1 (en) 2022-08-08 2024-02-15 Evonik Operations Gmbh Polyalkyl (meth)acrylate-based polymers with improved low temperature properties

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GB1068283A (en) 1967-05-10
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C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977