EP0744457B1 - Additif pour lubrifiants - Google Patents

Additif pour lubrifiants Download PDF

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Publication number
EP0744457B1
EP0744457B1 EP96107578A EP96107578A EP0744457B1 EP 0744457 B1 EP0744457 B1 EP 0744457B1 EP 96107578 A EP96107578 A EP 96107578A EP 96107578 A EP96107578 A EP 96107578A EP 0744457 B1 EP0744457 B1 EP 0744457B1
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EP
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Prior art keywords
meth
alkyl
pfp
group
acrylic acid
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EP96107578A
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German (de)
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EP0744457A2 (fr
EP0744457A3 (fr
Inventor
Clemens Dr. Auschra
Horst Dr. Pennewiss
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Roehm GmbH Darmstadt
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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
    • 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
    • C10M149/06—Macromolecular compounds obtained 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
    • 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
    • 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
    • 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
    • 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

Definitions

  • the invention relates to the use of macromonomers Graft polymers as lubricant additives with viscosity index improver and dispersant Effect.
  • comb polymers comb polymers
  • polymeric stabilizers for emulsions compare G. Allen, JC Bevington, Comprehensive Polymer Science Vol. 4 , pg. 248-250, Pergamon Press 1989.
  • Access to such comb polymers opens up the radical-initiated copolymerization of macromonomers with (chemically different) comonomers.
  • 5,254,632 discloses a relatively simple process for the preparation of suitable macromonomers in which (meth) acrylic acid esters are polymerized in the presence of a hydroxyl-containing sulfur regulator and the resulting hydroxyl-terminated polyalkyl (meth) acrylates with methyl methacrylate give the methacryloyl endblocked poly (meth) acrylate macromonomer transesterification.
  • the US patent also contains a compilation of relevant literature in which, inter alia, various ways of preparing the macromonomers are described.
  • British application GB-A-1,053,529 relates to oil-soluble copolymers and lubricating oil compositions prepared therefrom.
  • the copolymers are prepared by polymerizing esters of acrylic acid or methacrylic acid with relatively long-chain alcohols (C 12 to C 24 ) to a conversion of about 50-90%, then adding methyl and / or ethyl acrylate in a second step and then terminating is polymerized.
  • EP-A-0 382 493 describes oil-soluble, amine-containing Copolymers consisting of a main chain and a variety of polymers Side chains with basic amino groups exist.
  • the polymers can be prepared by either the amine-containing side chains on a Grafted polymer chain, or by first an amine-containing Macromonomer is prepared, which then with other monomers is copolymerized.
  • Comb polymers offer a variety of applications due to the structures of the use as Emulsifiers could claim special interest.
  • the structural features did not necessarily seem one particular suitability of such comb polymers as Viscosity Index Improver (VI improver) in Promise lubricating oils.
  • VI improver Viscosity Index Improver
  • VI improvers in particular dispersing VI improvers as lubricant additives.
  • the invention accordingly relates to the use of graft polymers PFP composed of polyalkyl methacrylate macromonomers (A) copolymerized with alkyl (meth) acrylates having C 6 -C 30 -alkyl radicals (AMA) with non-functionalized comonomers (B) selected from the group consisting from alkyl (meth) acrylates with C 1 -C 5 -alkyl radicals, styrene and alkylstyrenes with C 1 -C 4 -alkyl radicals and the vinyl esters and functionalized comonomers (C) selected from the group of (meth) acrylic esters, the (meth) acrylamides , the vinyl heterocycle, in a carrier medium TM as lubricant additives according to claim 1.
  • A polyalkyl methacrylate macromonomers
  • AMA alkyl (meth) acrylates having C 6 -C 30 -alkyl radicals
  • B selected from the group consist
  • the biradical radical X is an at least two- and up to 30-membered hydrocarbon chain, preferably with an -S-bridge directly following the polymeric part of I, it being possible for up to 9 carbon atoms to be replaced by ether oxygen.
  • the chain can still be replaced by functional radicals of the formula wherein R 9 is hydrogen or an alkyl radical having 1-8 carbon atoms, or a phenyl radical, to be interrupted.
  • R 11 is derived from industrial phenols or phenol mixtures are to be considered as particularly favorable.
  • the phenol itself mention may be made of tert-butylphenol, octylphenol, nonylphenol, dinonylphenol.
  • the functionalized comonomers (C) may belong to the group of formula VIII wherein R 10 is a 5- or 6-membered heterocycle containing at least one nitrogen atom.
  • the comonomers of the formula VIII are preferably selected from the group consisting of vinylpyrrolidones, such as 1-vinyl-2-pyrrolidone, vinylimidazole, N-vinylcarbazole, N-vinylsuccinimide, N-vinyloxazolidone, N-vinylphthalimide, vinylpyridines, such as 2-vinylpyridine.
  • vinylpyrrolidones such as 1-vinyl-2-pyrrolidone, vinylimidazole, N-vinylcarbazole, N-vinylsuccinimide, N-vinyloxazolidone, N-vinylphthalimide
  • vinylpyridines such as 2-vinylpyridine.
  • the macromonomer II-A can according to the following Weight relations be constructed: proportion AMA 0 - 90 % By weight, proportion of comonomer (B ') 0-40% by weight, proportion (C') 0 to 100% by weight.
  • the compounds of the formula X are obtained by polymerizing the monomers or monomer mixtures of the (meth) acrylic esters in the presence of an OH-functional regulator, preferably a sulfur regulator, for example in the presence of 2-mercaptoethanol (cf. -A 5,254,632).
  • OH-functional regulator preferably a sulfur regulator
  • 2-mercaptoethanol cf. -A 5,254,632
  • X assumes the structure - (CH 2 ) 2 S-.
  • other prior art methods which are suitable for producing a PAMA macromonomer having the same monomer composition with relatively high functionality of terminal polymerizable (activated) double bond can also be successfully used (see EP 261 942).
  • Suitable carrier medium TM for the graft polymers PFP are preferably inert, predominantly lipophilic solvents of the type customary in additive technology, in particular mineral oils, for example of the SN100 type such as Shell SM 920 or gas oils such as Shell G07.
  • the preparation of the macromonomers can in close analogy to US-A 5,254,632 or based on DE-A 23 18 809; W. Radke, AHE Müller, Polym. Prepr. Chem. Soc., Polym. Chem., 32 (1) 1991 and H. Rauch-Puntigam, Th. Völker, acrylic and methacrylic compounds, Springer-Verlag 1967.
  • a shielding gas such as For example, nitrogen, for example, to 95 degrees C.
  • the initiator for example one usual per compound such as a Perester - called tert.Butyl-2-ethylhexanoate - to and then metered in the AMA monomer preferably in admixture with further initiator, as a basis, about 0.4% by weight Initiator referred to the monomers, while about 3.5 hours too.
  • a Perester - called tert.Butyl-2-ethylhexanoate -
  • Initiator referred to the monomers
  • a suitable reaction vessel for example a 6 l three-necked flask with heating, stirring device, Internal thermometer, air inlet and packed column with regulator-controlled vapor conductor is a mixture of the hydroxyl-containing precursor with methyl (meth) acrylate as an indication, a weight ratio of about 4.3: 3 called - preferably together with at least one known polymerization inhibitor, for example Hydroquinone monomethyl ether and a stabilizer, for example of the HALS type, called e.g. 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxide in the usual quantities submitted and expediently under air passage to Heated reflux.
  • MMA Assumed transesterification component.
  • the transesterification catalyst preferably a lithium compound such as lithium methoxide added as a supporter is about 0.1% based on the Methacrylic acid methyl ester added and continue at reflux held until the boiling point has dropped, about 65 - 68 degrees C. Subsequently, further methanol-rich Distillate withdrawn until by increasing the Boiling temperature - be called about 100 degrees C - a extensive sales is displayed. After distilling off from further distillate (at 100 degrees C) is the approach cooled to room temperature and filtered. The excess methyl ester is advantageously removed on a vacuum rotary evaporator. The macromonomer is obtained A dissolved in the carrier medium TM.
  • a mixture is prepared with carrier medium TM added.
  • carrier medium TM a smaller part, about 6.5 wt .-% in about 10 times the amount of carrier medium in an apparatus as for the preparation of the hydroxyl group-containing precursor used under an inert gas such as nitrogen on elevated Temperature, as a stop is 82 degrees C, heated.
  • a macromonomer A preferably of low molecular weight, together with at least one dispersing monomer C, preferably together with a regulator, in particular a sulfur regulator, may be mentioned as an approximate 0.1% by weight, based on the macromonomers / monomers , submitted and heated under a protective gas such as nitrogen, for example, to 100 degrees C and initiator, for example of the type mentioned and in amounts of about 0.8 wt .-% added.
  • a protective gas such as nitrogen
  • initiator for example of the type mentioned and in amounts of about 0.8 wt .-% added.
  • further initiator is advantageously added in portions of about 1/5 of that already added, and it still lasts for a longer period of time, for about 12 hours at elevated temperature, for example at 100 ° C. Further advantageous variants of the production process can be taken from the examples.
  • the graft polymers PFP are distinguished by an outstanding action as a viscosity index improver.
  • the improved viscosity-temperature characteristics can be demonstrated by viscosity measurements on model formulations.
  • Of particular importance is also the invention to be recorded, excellent dispersing effect.
  • the particularly favorable dispersing efficiency is evidenced for example by results of laboratory tests.
  • the following examples serve to illustrate the invention.
  • the determination of the actual viscosity is carried out according to ASTM D 445.
  • the molecular weight is determined by size exclusion chromatography (SEC) using standard PMMA (compare HF Mark et al., Encyclopedia of Polymer Science & Engineering, Vol. 10 , pg., 1-19, J. Wiley, 1987).
  • SEC size exclusion chromatography
  • PMMA standard PMMA
  • Shear Stability Index PSSI Shear Stability Index
  • Example A-1a The same apparatus as in Example A-1a) is used.
  • the 6 l flask is charged with: 1.396 g of 100 N oil, 155.1 g of methacrylic acid ester of a mixture of C 11 -C 16 -alkanols (product DOBANOL 25L) and 3.10 g of 2-mercaptoethanol and under nitrogen to 110 ° C heated.
  • Example A-1a The same apparatus as for Example A-1a).
  • the 6 l flask is charged with: 1.396 g of 100 N oil, 155.1 g of methacrylic acid ester of a mixture of C 11 -C 16 -alkanols (product DOBANOL 25L) and 1.55 g of 2-mercaptoethanol and under nitrogen to 110 ° C heated.
  • a mixture of 2 448.9 g of the above methacrylic ester, 25.5 g of 2-mercaptopanol and 24.5 g of tert-butyl per 2-ethylhexanoate continuously pumped.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 227.7 g of macromonomer from Example A-1, 106.3 g of methacrylic acid ester of a mixture of C 11 -C 16 -alkanols (product DOBANOL 25 L) and 45.5 g of methyl methacrylate, 24.5 g of this monomer mixture are charged with 220.5 g of 100 N oil in the apparatus and heated to 82 degrees C under nitrogen.
  • Example A-1a The apparatus according to Example A-1a is used. 122.9 g of the macromonomer from Example A-2, 20.0 g of 2- (N-morpholinyl) -ethyl methacrylate and 0.15 g of dodecylmercaptan are placed in the three-necked flask and heated to 100 ° C. under nitrogen and then 1.0 g of tert Butylper-2-ethylhexanoate added. After 3 or 7 hours after the first initiator addition, in each case an additional 0.2 g of tert-butyl per-2-ethylhexanoate is added and the batch is kept at 100 ° C. for a further 12 hours. Yield:: 143 g of oil solution of the comb polymer PFP-2.
  • Example A-1 Apparatus as in Example A-1. 122.9 g of the macromonomer from Example A-3, 20 g of 2- (N-morpholinyl) -ethyl methacrylate and 0.15 g of dodecylmercaptan are placed in the three-necked flask and heated to 100 ° C. under nitrogen and then 1.0 g of tertiary Butylper-2-ethylhexanoate added. After 3 or 7 hours after the first initiator addition, in each case a further 0.2 g of initiator is added and the mixture is kept at 100 ° C. for a further 12 hours. Yield: 143 g of oil solution of the comb polymer PFP-3.
  • Example A-1 Apparatus as in Example A-1.
  • Example A-1 Apparatus as in Example A-1.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 299.5 g of macromonomer from Example A-1, 65 g of methacrylic acid ester of a mixture of C 11 to C 16 -alkanols (product Dobanol 25 L), 65.0 g of methyl methacrylate and 70.5 g of 100 N oil , 50 g of this monomer mixture are placed in the apparatus and heated to 90 degrees C under nitrogen. After addition of 0.06 g of tert-butyl per-2-ethylhexanoate to the template, 450 g of the monomer mixture are continuously pumped in over 3.5 hours together with 0.59 g of tert-butyl 2-ethylhexanoate.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 276.5 g macromonomer from Example A-1, 120.0 g n-butyl methacrylate and 103.5 g 100 N oil.
  • 75 g of this monomer mixture are placed in the apparatus and heated to 90 degrees C under nitrogen.
  • 425 g of the monomer mixture are continuously pumped in over 3.5 hours together with 0.51 g of tert-butyl per-2-ethylhexanoate.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 207.4 g macromonomer from Example A-1, 165.0 g n-butyl methacrylate and 127.6 g 100 N oil. 75 g of this monomer mixture are introduced into the apparatus and heated to 85 ° C. under nitrogen. After addition of 0.09 g of tert-butyl per-2-ethylhexanoate for submission, 425 g of the monomer mixture are continuously pumped in over 3.5 hours together with 0.51 g of tert-butyl per-2-ethylhexanoate. 1.5 hours after the end of the feed, 250 g of 100 N oil are added for dilution.
  • Graft polymers For testing the emulsifier effect of Graft polymers may be the following toluene-water emulsified test for testing the dispersing effect of Soot-spot test can be applied.
  • the quantification of the emulsifying effect in% values takes place according to the scheme shown in Fig. 1b. This is the proportion of the observation period 5 minutes to 24 Hours present emulsion by the ratio of Area A is characterized by the total area A + B and in% values specified.
  • the additive to be tested is dissolved in 150 N oil (Enerpar 11) mixed two stock solutions: stock solution I with 0.375% polymer content and stock solution II with 0.75% Polymer content. From each stock solution become 2 Soot dispersion solutions prepared (double determination). For this purpose, in each case in a 150 ml beaker 1.5 g of carbon black (Flame black, Degussa special black 4) and 50 g stock solution weighed and then with an Ultra-Turrax Intensive stirrer stirred for 30 minutes at 9,000 u / minute. Thereafter, 20 ⁇ l of each dispersion solution Filter paper (paper Durieux 122) spotted. After 48 Hours of even storage at 30 degrees C will be the Punctuated flecks evaluated. For this, the diameter of the Soot stain and the diameter of the surrounding it Oil spill measured and their ratio in% stated:
  • the total score of the spot test is the sum of the four percentage ratings. Products with poor soot dispersion give overall ratings of about 70% and lower, products with good carbon black dispersion give overall ratings of ⁇ 130%.

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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)
  • Lubricants (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Graft Or Block Polymers (AREA)

Claims (4)

  1. Utilisation de polymères greffés PFP qui sont constitués à partir de
    a) 10 à 90 % en poids, rapporté au PFP, de macromonomères de méthacrylate de polyalkyle (A) qui sont copolymérisés avec,
    b) de 0 à 90 % en poids, rapporté au PFP, d'esters alkyliques d'acide (méth)acrylique (AMA) ayant des restes alkyle en C6-C30 et avec,
    c) de 0 à 60 % en poids, rapporté au PFP, de comonomères non fonctionnalisés (B) choisis dans le groupe qui consiste en les esters alkyliques d'acide (méth)acrylique ayant des restes alkyle en C1-C5, le styrène, les alkylstyrènes ayant des restes alkyle en C1-C4 et les esters vinyliques d'acide gras ayant de 2 à 12 atomes de carbone dans le reste acide gras,
    ainsi que
    d) de 0 à 40 % en poids, rapporté au PFP, de comonomères fonctionnalisés (C) choisis dans le groupe qui consiste en des esters et des hétérocycles vinyliques,
    avec la précision que la somme des monomères copolymérisés b) à d) rapporté au PFP représente de 10 à 90 % en poids,
    dans un milieu support TM en tant qu'additif de lubrifiant ayant une action qui améliore l'indice de viscosité.
  2. Utilisation conformément à la revendication 1,
    caractérisé en ce que
    les macromonomères de méthacrylate polyalkyliques (A) représentent des composés de formule II,
    Figure 00400001
    où
    X =
    reste biradicalaire
    R1 =
    -H ou -CH3
    R2 =
    -H ou -CH3
    n =
    6 à 30
    p =
    degré moyen de polymérisation du macromonomère
    avec la précision que MW, le poids moléculaire moyen pondéral du macromonomère de formule II se situe dans la zone de 1000 à 100.000.
  3. Utilisation conformément aux revendications 1 et 2,
    caractérisée en ce que
    le poids moléculaire moyen pondéral du polymère greffé PFP se situe dans la zone de 5.000 à 1.000.000.
  4. Utilisation conformément à la revendication 1 renfermant comme polymère greffé, les polymères greffés PFP' qui sont constitués pour,
    a) de 10 à 90 % en poids de macromonomères de méthacrylate polyalkyle (A'), contenant,
    (a1) de 0 à 90 % en poids d'ester (méth)acrylique d'alkyle (AMA') ayant des restes alkyle en C6 à C30,
    (a2) de 0 à 40 % en poids de comonomères (B') non fonctionnalisés choisis dans le groupe qui consiste en les esters d'alkyle d'acide (méth)acrylique avec des restes alkyle en C1-C5 le styrène, les alkylstyrènes, ayant des restes alkyle en C1-C4, et des esters vinyliques d'acide gras ayant de 2 à 12 atomes de carbone dans le reste d'acide gras, ainsi que
    (a3) de 0 à 100 % en poids de comonomères fonctionnalisés (C') choisis dans le groupe qui consiste en des esters et des amides d'acide (méth)acrylique fonctionnalisés et des hétérocycles vinyliques,
    avec la précision que la somme des monomères (AMA'), (B') et (C') dans les macromonomères (A') se complète à 100 % en poids,
    b) des 0 à 90 % en poids de monomères choisis dans le groupe qui consiste en des esters alkyliques d'acide (méth)acrylique (AMA) avec des restes alkyle en C6-C30,
    c) de 0 à 60 % en poids de monomères (B) choisis dans le groupe qui consiste en les esters alkyliques d'acide (méth)acrylique ayant des restes alkyle en C1-C5, le styrène, les alkylstyrènes ayant des restes alkyle en C1-C4, et les esters vinyliques d'acide gras ayant de 2 à 12 atomes de carbone dans le reste acide gras,
    d) de 0 à 40 % en poids de comonomères fonctionnalisés (C) choisis dans le groupe qui consiste en les esters et en les amides d'acide (méth)acrylique fonctionnalisés et des hétérocycles vinyliques, avec la précision que la somme des monomères copolymérisés (AMA), (B) et (C) rapporté au PFP' représente de 10 à 90 % en poids.
EP96107578A 1995-05-22 1996-05-13 Additif pour lubrifiants Expired - Lifetime EP0744457B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19518786 1995-05-22
DE19518786A DE19518786A1 (de) 1995-05-22 1995-05-22 Schmierstoffadditive

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EP0744457A2 EP0744457A2 (fr) 1996-11-27
EP0744457A3 EP0744457A3 (fr) 1997-09-24
EP0744457B1 true EP0744457B1 (fr) 2003-09-24

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US (1) US5756433A (fr)
EP (1) EP0744457B1 (fr)
JP (2) JP4142121B2 (fr)
AT (1) ATE250659T1 (fr)
DE (2) DE19518786A1 (fr)
SG (1) SG54334A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11365273B2 (en) 2019-12-16 2022-06-21 Infineum International Limited High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same
US11384311B2 (en) 2019-12-16 2022-07-12 Infineum International Limited High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same
US11685874B2 (en) 2019-12-16 2023-06-27 Infineum International Limited High viscosity index comb polymer viscosity modifiers and methods of modifying lubricant viscosity using same

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19518786A1 (de) * 1995-05-22 1996-11-28 Roehm Gmbh Schmierstoffadditive
US5955405A (en) * 1998-08-10 1999-09-21 Ethyl Corporation (Meth) acrylate copolymers having excellent low temperature properties
US6495618B1 (en) 1999-12-17 2002-12-17 E. I. Du Pont De Nemours And Company Graft copolymer with an amide functional group as a pigment dispersant
US6642189B2 (en) 1999-12-22 2003-11-04 Nippon Mitsubishi Oil Corporation Engine oil compositions
US6323164B1 (en) * 2000-11-01 2001-11-27 Ethyl Corporation Dispersant (meth) acrylate copolymers having excellent low temperature properties
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SG54334A1 (en) 1998-11-16
DE59610726D1 (de) 2003-10-30
EP0744457A2 (fr) 1996-11-27
DE19518786A1 (de) 1996-11-28
JP2008255359A (ja) 2008-10-23
ATE250659T1 (de) 2003-10-15
EP0744457A3 (fr) 1997-09-24
JP4142121B2 (ja) 2008-08-27
JPH08311133A (ja) 1996-11-26
US5756433A (en) 1998-05-26

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