EP0140274B1 - Additifs pour huile lubrifiante - Google Patents

Additifs pour huile lubrifiante Download PDF

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Publication number
EP0140274B1
EP0140274B1 EP84112445A EP84112445A EP0140274B1 EP 0140274 B1 EP0140274 B1 EP 0140274B1 EP 84112445 A EP84112445 A EP 84112445A EP 84112445 A EP84112445 A EP 84112445A EP 0140274 B1 EP0140274 B1 EP 0140274B1
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EP
European Patent Office
Prior art keywords
mol
esters
proportion
component
acrylic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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EP84112445A
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German (de)
English (en)
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EP0140274A2 (fr
EP0140274B2 (fr
EP0140274A3 (en
Inventor
Horst Dr. Dipl.-Chem. Pennewiss
Heinz Jost
Helmut Knöll
Ulrich Dr. Dipl.-Phys. Schödel
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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Classifications

    • 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
    • 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
    • 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
    • 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
    • C10M157/00—Lubricating compositions characterised by the additive being a mixture of two or more macromolecular compounds covered by more than one of the main groups C10M143/00 - C10M155/00, 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
    • 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
    • C10M2205/06—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing conjugated dienes
    • 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
    • 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

Definitions

  • the invention relates to multifunctional lubricating oil additives based on polyalkyl acrylates and polyalkyl methacrylates as well as systems formed from olefin copolymers (OCP) or hydrogenated styrene-diene copolymers (HSD) and PAMA.
  • OCP olefin copolymers
  • HSD hydrogenated styrene-diene copolymers
  • Lubricating oils generally contain n-paraffin hydrocarbons, which on the one hand have a favorable effect on the setting of good viscosity / temperature behavior, but on the other hand, Cooling will fail in crystalline form and thereby impair or completely prevent the flow of the oils ("stagnation").
  • An improvement in the low-temperature flow properties can be achieved by dewaxing. Since the costs increase considerably if one wants to lower the "pour point" beyond certain values, one generally only partially dewaxes the oils down to a pour point in the range of -15 ° C. and uses the further reduction Pour point (down to about -40 ° C) so-called pour point depressants, which effectively reduce the pour point already in concentrations between 0.05 and 1%. The following idea is decisive:
  • Paraffin-like compounds are built into the growing paraffin crystal surfaces and thus prevent the crystals from growing further and the formation of extensive crystal groups.
  • pour point improvers For the mode of action of such pour point improvers, it applies that they have certain structural elements, namely sufficiently long alkyl groups to be incorporated into the growing paraffin crystals from the nucleation and side chains or side groups at greater intervals to disrupt crystal growth. (See Ullmanns, Encyklopedia of technical chemistry, 4th edition, volume 20, Verlag Chemie, 1981, p. 548).
  • Technically applicable pour point depressants on the other hand, must be required to have good thermal, oxidative and chemical stability, shear strength and the like. have.
  • the currently preferred pour point depressants are polymethacrylates, which already lower the pour point of lubricating oils sufficiently in a concentration of 0.1-0.5% (cf. US Pat. No. 2,091,627, US Pat. No. 2 100 993, US Pat. PS 2 114 233).
  • the carbon number of the alkyl radicals is between 12 and 18, the branching wheel between 10 and 30 mol%.
  • Polymethacrylates in the M range between approx. 5,000 and 500,000 are available, which allow the flow behavior of light, low-molecular to heavy, high-molecular lubricating oils to be improved.
  • the FR-A 2 407 259 has set itself the task of the pour point of a so-called non-classic oil, namely a hydrocracked base oil with a particularly high V.I. (XHVI- ⁇ I with V.I. of at least 140 according to ASTM D-2270).
  • non-classic oil namely a hydrocracked base oil with a particularly high V.I. (XHVI- ⁇ I with V.I. of at least 140 according to ASTM D-2270).
  • Such oils are not special cases directly comparable to "classic" oils.
  • multifunctional additives for mineral oils are also said to improve the viscosity / temperature behavior at high and low temperatures. This requires, compared to pure pour point improvers, larger additional amounts in the range between 1-30% by weight.
  • multifunctional viscosity index improvers can also have dispersing / detergent properties (cf. Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 20, loc.cit., Pp. 457-671) .
  • These multifunctional VI improvers are mostly based on polymethacrylic acid esters (PAMA) and combinations (mixed polymers) of PAMA with olefin copolymers (OCP) or hydrogenated styrene-diene copolymers (HSD) and less on the basis of OCP or HSD alone.
  • PAMA polymethacrylic acid esters
  • OCP olefin copolymers
  • HSD hydrogenated styrene-diene copolymers
  • the object on which the present invention is based relates to improving the viscosity / temperature behavior of mineral oils containing n-paraffin in the broadest sense, especially at low temperatures, caused by the tendency of the n-paraffins to crystallize.
  • This task in one of its particularly acute forms is explained in more detail using the example of n-paraffin-containing lubricating oils:
  • base oils poorer quality mineral oils
  • Lubricating oils for the purposes of the present invention are paraffin-based and naphthenic-based vacuum distillate oils.
  • the additives according to the invention also contain VI-improving polyolefins / olefin copolymers (OCP) and / or hydrogenated styrene-diene polymers (HSD), preferably of the type of the combination of polyalkyl (meth) acrylates (PAMA) and OCP (mixed Polymers) as described in DE-PS 29 05 954 and US-PS 4,290,925.
  • OCP VI-improving polyolefins / olefin copolymers
  • HSD hydrogenated styrene-diene polymers
  • the proportion of the olefin copolymers and of the hydrogenated styrene-diene polymers or of the polymers according to the cited DE-PS 29 05 954 or US Pat. No. 4,290,925 in the additives can be 10-70% by weight.
  • the proportion of the polymers (P) in the additives according to the invention is 10-80% by weight, the total content of polymers is 20-80% by weight.
  • the proportion of component a) in the polymer P is preferably 50-100 mol%, especially 100 mol%.
  • the proportion of component b ') in the polymer P 2 is preferably 20-40 mol%.
  • the polymer P 2 is composed only of components a ') and b').
  • acrylic or methacrylic acid esters with straight-chain unbranched C 10 -C 14 alcohols for example prepared by the Ziegler process by hydrolysis of aluminum alkoxides. Examples include the Lorole @ products from Henkel KG. Düsseldorf and Alfole °, products from Condea, Hamburg).
  • components b) and b ') are preferably acrylic or methacrylic acid esters of straight-chain, unbranched C 16 -C 24 alcohols, especially C 18 -C 22 alcohols.
  • the tallow fatty alcohols and Alfole® (products from Condea) may be mentioned.
  • the molecular weights Mw of the polymers P are generally in the range from 50,000 to 500,000, those of the polymers P 2 in the range from 50,000 to 500,000.
  • the polymers P 1 and P 2 can be prepared by the customary radical polymerization processes.
  • Component e) of the polymers P 1 is by definition radical-polymerizable monomers with functional groups in the molecule, in particular those whose positive effect on oil additives in the sense of dispersing or detergent activity is known.
  • compounds of the general formula 1 may be mentioned wherein R, hydrogen or methyl and Bs is an (inert) heterocyclic 5- or 6-membered ring or a radical means, where Z is oxygen or a radical -NR 4 and Q are an optionally alkylated hydrocarbon bridge with a total of 2 to 10 carbon atoms and R 2 and R 3 are each an alkyl radical with 1 to 6 carbon atoms or together including nitrogen and optionally others Heteroatoms can form a heterocyclic 5- or 6-membered ring and in which R 4 represents hydrogen or an alkyl radical having 1 to 6 carbon atoms.
  • Examples include C- and N-vinylpyridine, vinylpyrrolidone, vinylcarbazole, vinylimidazole and their alkyl derivatives, in particular the N-vinyl compounds, also the dialkylaminoalkyl esters of (meth) acrylic acid, especially dimethylaminoethyl acrylate and methacrylate, dimethylaminopropylacrylate, methacrylate and the corresponding amide (methacrylate) - or -methacrylamides) such as dimethylaminopropyl (meth) acrylamide.
  • the above definitions (formula I) also apply to e ') in the polymer P 2 .
  • the solvents (L) used in the additives according to the invention are those known for lubricant oil additives, in particular paraffin- or naphthenic-based mineral oils or the known ester oils or poly-a-olefins. (See Ullmanns Encyklopadie der techn. Chemie, Volume 20, loc.cit., Pp. 483-529).
  • the preparation of the polymers follows the polymerization processes of the prior art.
  • a mixture of mineral oil and a monomer mixture of a), b), c), d) and e) is placed in a reaction vessel which is suitably equipped with a stirrer, thermometer, reflux condenser and metering line.
  • the mixture Under a C0 2 atmosphere and stirring, the mixture is heated to about 90-100 ° C. After this temperature has been reached and initiator (preferably per compounds such as peresters, peroxides or azo compounds) has been added, a mixture of the monomers a), b), c), d) and e) and further initiator are metered in; approx. 2 hours after the end of the feed, further initiator is fed.
  • the total amount of initiator is generally 1-3% by weight, based on the total amount of monomers.
  • the total polymerization time is generally 8-9 hours.
  • a viscous solution with a polymer content of generally 40-70% by weight is obtained.
  • One component is placed in a suitable container and heated to approx. 80-120 ° C with stirring.
  • the admixing components are also heated to approx. 80-120 ° C and metered in as quickly as possible with stirring.
  • the additive according to the invention possibly together with other additives, such as DI package and OCP-VI improver, is dissolved in the base oil at 50-60 ° C. with stirring.
  • the additives according to the invention can be added to the lubricating oils in a manner known per se.
  • Oil formulations containing the additives according to the invention in addition to the required viscosity data at 100 ° C., show very favorable values for pour point and stable pour point as well as excellent viscosity data at -15 ° C. to 40 ° C.
  • Feed 1 is metered in uniformly within 210 minutes. 120 minutes after the end of the inlet, inlet 2 is started:

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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)

Claims (2)

1. Additifs pour huiles de graissage contenant des n-paraffines, à base de polyméthacrylates et polyacrylates d'alkyle, qui peuvent être adapatés à la teneur en paraffines des diverses huiles de graissage, et à base des solvants usuels, caractérisés en ce que les additifs contiennent des mélanges d'un premier composant polymère (P) constitué de
I. 10-99% en poids d'un ou de plusieurs polymère(s) P1, composé(s) de
a) esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools à chaîne droite, non ramifiée, comportant au moins 6 et au plus 15 atomes de carbone et
b) esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools à chaîne droite non ramifiée comportant de 16 à 30 atomes de carbone et
c) esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools ramifiés comportant de 8 à 40 atomes de carbone,
d) esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools comportant de 1 à 5 atomes de carbone,
e) monomères copolymèrisables par polymérisation radicalaire qui présentent des groupes fonctionnels dans leur molécule,
où la proportion du composant a) s'élève à 10 à 100% en moles, la proportion du composant b) à 0-5% en moles, la proportion du composant c) à 0-90% en moles, la proportion du composant d) à 0-50% en moles et la proportion du composant e) à 0-20% en moles, à chaque fois par rapport au polymère P1, et
II. 90-1 % en poids d'un ou plusieurs polymères P2, composé(s) de
a') esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools non ramifiés à chaîne droite ayant au moins 6 et au plus 15 atomes de carbone et
b') esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools à chaîne droite non ramifiée ayant de 16 à 30 atomes de carbone et
c') esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools ramifiés ayant de 8 à 40 atomes de carbone et
d') esters de l'acide méthacrylique, de l'acide acrylique ou des deux avec des alcools comportant de 1 à 5 atomes de carbone,
e') monomères copolymérisables par polymérisation radicalaire qui présentent des groupes fonctionnels dans leur molécule,
où la proportion du composant a') s'élève à 30-90% en moles, la proportion du composant b') à 10-70% en moles, la proportion du composant c') à 0-90% en moles, la proportion du composant d') à 0-50% en moles et la proportion du composant e') à 0-20% en moles, à chaque fois par rapport au polymère P2, et d'un deuxième composant polymère choisi dans le groupe des copolymères d'oléfines améliorant l'indice de viscosité et des copolymères styrène-diène hydrogénés, sous réserve que les copolymères d'oléfine soient constitués d'éthylène, de propylène, de butylène ou d'isobutylène, sur quoi sont greffés des monomères du groupe des composants a), b), c), ou sous la forme d'une émulsion de polymères concentrée, qui contient, comme phase continue, des poly(méth)acrylates, un milieu support qui est un bon solvant pour les poly(méth)acrylesters, et un moins bon solvant pour les copolymères d'oléfine à cause de sa teneur en esters d'acide poly(méth)acrylique, et, comme stabilisateur pour la dispersion de phases, un polymère greffé ou un polymère séquence fait de copolymères d'oléfines et d'esters d'acide (méth)acrylique, outre le solvant L.
2. Additifs selon la revendication 1, caractérisés en ce que la proportion des polymères (P), des copolymères d'oléfines (OCP) et des copolymères styrènediène hydrogénés (HSD) s'élève à 20-80% en poids, par rapport aux additifs.
EP84112445A 1983-10-28 1984-10-16 Additifs pour huile lubrifiante Expired - Lifetime EP0140274B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3339103 1983-10-28
DE19833339103 DE3339103A1 (de) 1983-10-28 1983-10-28 Additive fuer schmieroele

Publications (4)

Publication Number Publication Date
EP0140274A2 EP0140274A2 (fr) 1985-05-08
EP0140274A3 EP0140274A3 (en) 1987-05-13
EP0140274B1 true EP0140274B1 (fr) 1990-12-05
EP0140274B2 EP0140274B2 (fr) 1994-06-22

Family

ID=6212932

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84112445A Expired - Lifetime EP0140274B2 (fr) 1983-10-28 1984-10-16 Additifs pour huile lubrifiante

Country Status (4)

Country Link
US (1) US4968444A (fr)
EP (1) EP0140274B2 (fr)
JP (1) JPH0631382B2 (fr)
DE (2) DE3339103A1 (fr)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
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DE3544061A1 (de) * 1985-12-13 1987-06-19 Roehm Gmbh Hochscherstabile mehrbereichsschmieroele mit verbessertem viskositaetsindex
DE3607444A1 (de) * 1986-03-07 1987-09-10 Roehm Gmbh Additive fuer mineraloele mit stockpunktverbessernder wirkung
DE3613992C2 (de) * 1986-04-25 2000-05-04 Roehm Gmbh Additive für paraffinische Schmieröle
US4844829A (en) * 1987-08-19 1989-07-04 Pennzoil Products Company Methacrylate pour point depressants and compositions
DE3889533T2 (de) * 1987-08-19 1994-12-01 Pennzoil Prod Co Giesspunkterniedrigende methacrylatadditive und -zusammensetzungen.
US4956111A (en) * 1987-08-19 1990-09-11 Pennzoil Products Company Methacrylate pour point depressants and compositions
US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
DE3905681A1 (de) * 1989-02-24 1990-08-30 Basf Ag Konzentrierte mischungen von pfropfcopolymerisaten aus estern von ungesaettigten saeuren und ethylen-vinylester-copolymerisaten
DE3930142A1 (de) * 1989-09-09 1991-03-21 Roehm Gmbh Dispergierwirksame viskositaets-index-verbesserer
US5149452A (en) * 1990-12-19 1992-09-22 Exxon Research And Engineering Company Wax isomerate having a reduced pour point
FR2679444B1 (fr) * 1991-07-25 1995-04-07 Oreal Utilisation comme agents epaississants des huiles, dans une composition cosmetique huileuse, d'une association de deux copolymeres.
US5229021A (en) * 1991-12-09 1993-07-20 Exxon Research & Engineering Company Wax isomerate having a reduced pour point
US5534175A (en) * 1992-12-28 1996-07-09 The Lubrizol Corporation Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers
HUT69298A (en) 1993-07-23 1995-09-28 Rohm & Haas Method of making a copolymer useful as viscosity index improving additive for hydraulic fluids
US5416162A (en) * 1993-09-20 1995-05-16 Rohm And Haas Company Compatibilizer for a viscosity index improving polymer blend
JP2748104B2 (ja) * 1994-03-08 1998-05-06 三洋化成工業株式会社 粘度指数向上剤及び潤滑油
US6228819B1 (en) 1994-04-14 2001-05-08 Rohm And Haas Company Process for making a viscosity index improving copolymer
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JPS60110790A (ja) 1985-06-17
EP0140274A2 (fr) 1985-05-08
JPH0631382B2 (ja) 1994-04-27
US4968444A (en) 1990-11-06
EP0140274B2 (fr) 1994-06-22
EP0140274A3 (en) 1987-05-13
DE3339103A1 (de) 1985-05-09
DE3483714D1 (de) 1991-01-17

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