EP0744457A2 - Additif pour lubrifiants - Google Patents

Additif pour lubrifiants Download PDF

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Publication number
EP0744457A2
EP0744457A2 EP96107578A EP96107578A EP0744457A2 EP 0744457 A2 EP0744457 A2 EP 0744457A2 EP 96107578 A EP96107578 A EP 96107578A EP 96107578 A EP96107578 A EP 96107578A EP 0744457 A2 EP0744457 A2 EP 0744457A2
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EP
European Patent Office
Prior art keywords
pfp
weight
alkyl
meth
functionalized
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EP96107578A
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German (de)
English (en)
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EP0744457B1 (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 graft polymers obtained from macromonomers as lubricant additives with a viscosity index-improving and dispersing action.
  • So-called comb polymers have been available to the technology for some time, and have been used, for example, as polymer stabilizers for emulsions (cf. G. Allen, JC Bevington, Comprehensive Polymer Science Vol. 4 , pg. 248-250, Pergamon Press 1989).
  • the radical-initiated copolymerization of macromonomers with (chemically different) comonomers provides access to such comb polymers.
  • 5,254,632 specifies a relatively simple process for the preparation of suitable macromonomers, in which (meth) acrylic acid esters are polymerized in the presence of a sulfur regulator containing hydroxyl groups and the hydroxyl-terminated polyalkyl (meth) acrylates thus obtained are transesterified with methyl methacrylate to form poly (meth) acrylate macromonomers with a methacryloyl end group .
  • the US patent also contains a compilation of relevant literature in which, among other things, various ways of producing the macromonomers are described.
  • the biradical radical X preferably represents an at least two- and up to 30-membered hydrocarbon chain, preferably with an -S bridge directly after the polymeric part of I, it being possible for up to 9 carbon members to be replaced by ether oxygen.
  • the chain can also be formed by functional radicals of the formula in which R 9 represents hydrogen or an alkyl radical having 1-8 carbon atoms, or a phenyl radical.
  • R 11 derives from technical phenols or phenol mixtures are particularly favorable.
  • tert-butylphenol, octylphenol, nonylphenol and dinonylphenol should be mentioned.
  • the functionalized comonomers (C) can also belong to the group of the 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 be constructed according to the following weight ratios: AMA content 0 - 90% by weight, comonomer (B ') content 0 - 40% by weight, (C') content 0 to 100% by weight .
  • the compounds of the formula X are obtained by using the monomers or monomer mixtures (Meth) acrylic ester polymerized in the presence of an OH-functional regulator, preferably a sulfur regulator, for example in the presence of 2-mercaptoethanol (cf. US Pat. No. 5,254,632). In the latter case, X adopts the structure - (CH 2 ) 2 S-.
  • an OH-functional regulator preferably a sulfur regulator
  • 2-mercaptoethanol cf. US Pat. No. 5,254,632
  • X adopts the structure - (CH 2 ) 2 S-.
  • other methods of the prior art which are suitable for the production of a PAMA macromonomer with the same monomer composition with a relatively high functionality at a terminal polymerizable (activated) double bond can also be used with good success (cf. EP 261 942).
  • macromonomers (A) made up of (meth) acrylic esters of commercially available mixtures of alcohols in the claimed C 6 -C 30 range, in particular in the range of average C numbers from approx. 10 to approx. 20, especially in the range of approx. 12 - 18, especially with a focus on the ranges 12.2 - 15.
  • examples include (methacrylic acid esters of a mixture of C 11 -C 16 alcohols with an average C number of 13.2 - 13.8 ( Commercial product DOBANOL 25L from Shell AG).
  • 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 macromonomers can be prepared in close analogy to US Pat. No. 5,254,632 or based on DE-A 23 18 809; W. Radke, AHE Müller, Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem) 32 (1) 1991 and H. Rauch-Puntigam, Th. Völker, Acryl- und Methacrylitatien, Springer-Verlag 1967.
  • a mixture of the alkyl (meth) acrylates AMA together with the molecular weight regulator, such as mercaptoethanol - approx. 1.0% by weight based on the monomers may be mentioned - in a suitable reaction vessel, such as a three-necked flask with heating , Stirrer, internal thermometer, gas inlet device and reflux condenser in, for example, about 10 times the amount of the carrier medium TM and heated with the introduction of a protective gas such as nitrogen, for example to 95 degrees C.
  • a suitable reaction vessel such as a three-necked flask with heating , Stirrer, internal thermometer, gas inlet device and reflux condenser in, for example, about 10 times the amount of the carrier medium TM and heated with the introduction of a protective gas such as nitrogen, for example to 95 degrees C.
  • the initiator for example a per compound which is customary per se, for example a perester - tert-butyl-2-ethylhexanoate is mentioned - and then the AMA monomer is preferably metered in as a mixture with another initiator, about 0.4% by weight of initiator based on the monomers are mentioned as a guide, while about 3.5 Hours too.
  • about half of the initiator is added at certain intervals after the end of the feed - about every 2.5 hours and after 5 hours - and is maintained over a longer period, about 12 hours approx. 95 degrees C. It is then expedient to dilute with the TM carrier medium.
  • a mixture of the hydroxyl group-containing precursor with methyl (meth) acrylate - a weight ratio of about 4.3: 3 is mentioned as an indication -
  • at least one known polymerization inhibitor for example hydroquinone monomethyl ether and a stabilizer, for example of the HALS type, for example 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxide is presented in the usual amounts and is expedient heated to reflux while passing air.
  • MMA is assumed to be the transesterification component.
  • the transesterification catalyst preferably a lithium compound such as lithium methoxide is added, about 0.1% based on the methacrylic acid methyl ester is added as a reference and is kept at reflux until the boiling point has dropped, approximately to 65-68 degrees C. Subsequently, further methanol-rich distillate is drawn off until a substantial conversion is indicated by an increase in the boiling temperature - about 100 degrees C should be mentioned. After distilling off further distillate (at 100 degrees C), the mixture is cooled to room temperature and filtered. The excess methyl ester is advantageously removed on a vacuum rotary evaporator. The macromonomer A is obtained dissolved in the carrier medium TM.
  • a mixture is prepared from the macromonomer A, preferably prepared as described above, and the AMA monomer and optionally the comonomer B in the desired ratio, and the carrier medium TM is added.
  • the carrier medium TM is added.
  • a smaller part, about 6.5% by weight in about 10 times the amount of carrier medium is used in an apparatus such as for the preparation of the hydroxyl group-containing precursor under a protective gas such as nitrogen at elevated temperature, 82 degrees C as a reference, warmed up.
  • a protective gas such as nitrogen at elevated temperature, 82 degrees C as a reference, warmed up.
  • the further monomer mixture together with initiator is added within a certain period of time, for example 3.5 hours, advantageously by continuous pumping. After a longer period of time from the end of the feed, approx.
  • a macromonomer A preferably of low molecular weight, is used in the apparatus described above together with at least one dispersant monomer C, preferably together with a regulator, in particular a sulfur regulator, about 0.1% by weight, based on the macromonomers / monomers, are provided as a reference and heated under a protective gas such as nitrogen, for example to 100 Grade C and initiator, for example of the type mentioned and added in amounts of approximately 0.8% by weight. It is advantageous to add a further initiator at intervals of a few hours, for example after 3 and 7 hours, advantageously in portions of about 1/5 of the amount already added, and to hold for a longer period, for example about 12 hours at elevated temperature, for example at 100 degrees C. Further advantageous variants of the manufacturing process can be found in the examples.
  • the graft polymers PFP according to the invention are notable for excellent action as viscosity index improvers.
  • the improved viscosity-temperature characteristics can be demonstrated using viscosity measurements on model formulations.
  • Also of particular importance is the excellent dispersing action to be observed according to the invention.
  • the particularly favorable dispersing effectiveness is demonstrated, for example, by the results of laboratory tests.
  • the current viscosity is determined in accordance with ASTM D 445.
  • the molecular weight is by "Size Exclusion Chromatography" (SEC) determined with standard PMMA (cf. HF Mark et al. Encyclopedia of Polymer Science & Engineering, Vol. 10 , pg. 1-19, J. Wiley 1987).
  • SEC Size Exclusion Chromatography
  • PMMA cf. HF Mark et al. Encyclopedia of Polymer Science & Engineering, Vol. 10 , pg. 1-19, J. Wiley 1987.
  • the 100 N oil used in the examples represents a Shell SM 920.
  • shear stability index PSSI shear stability index
  • 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 placed in the apparatus with 220.5 g of 100 N oil and heated to 82 ° 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 dodecyl mercaptan are placed in a three-necked flask and heated to 100 ° C. under nitrogen and then 1.0 g of tert .-Butylper-2-ethylhexanoate admitted. After 3 or 7 hours after the first initiator addition, a further 0.2 g of tert-butyl per-2-ethylhexanoate are added and the mixture is kept at 100 ° C. for a further 12 hours. Yield:: 143 g 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 dodecyl mercaptan are placed in a 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, a further 0.2 g of initiator are 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-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 ° C. under nitrogen. After adding 0.06 g of tert-butyl per-2-ethylhexanoate to the initial charge, 450 g of the monomer mixture together with 0.59 g of tert-butyl-2-ethylhexanoate are pumped in continuously over the course of 3.5 hours.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 276.5 g of macromonomer from Example A-1, 120.0 g of n-butyl methacrylate and 103.5 g of 100 N oil. 75 g of this monomer mixture are placed in the apparatus and heated to 90 ° C. under nitrogen. After adding 0.09 g of tert-butyl per-2-ethylhexanoate to the initial charge, 425 g of the monomer mixture together with 0.51 g of tert-butyl per-2-ethylhexanoate are pumped in continuously over the course of 3.5 hours.
  • Example A-1a An apparatus according to Example A-1a is used.
  • the monomer mixture is prepared from 207.4 g of macromonomer from Example A-1, 165.0 g of n-butyl methacrylate and 127.6 g of 100 N oil. 75 g of this monomer mixture are placed in the apparatus and heated to 85 ° C. under nitrogen. After adding 0.09 g of tert-butyl per-2-ethylhexanoate to the initial charge, 425 g of the monomer mixture together with 0.51 g of tert-butyl per-2-ethylhexanoate are pumped in continuously within 3.5 hours. 1.5 hours after the end of the feed 250 g are used for dilution 100 N oil added.
  • the toluene-water emulsification test given below can be used to test the dispersing action of the soot spot test.
  • toluene / water emulsification test The additive to be tested for its emulsifying action is dissolved in toluene (mixed with 20 ppm Oracet Blue B) with a polymer concentration of 1% by weight. 7 ml of the water and 13 ml of the 1% toluene solution are poured into a graduated 20 ml ground test tube in succession and the temperature is controlled in a water bath at 30 ° C. for 15 minutes. A uniform emulsion is created by shaking the test tube vigorously and the sample is returned to the temperature control bath. The separation of the emulsion into the layers of toluene, emulsion and water is observed over a period of 24 hours. For this purpose, the toluene / emulsion layer boundary and the emulsion / water layer boundary are read from the graduation at the times of 5 minutes, 10 minutes, 100 minutes and 24 hours (see Fig. 1a).
  • the quantification of the emulsifying effect in% values takes place according to the scheme shown in Fig. 1b.
  • the proportion of the emulsion present for 5 minutes to 24 hours during the observation period is characterized by the ratio of area A to total area A + B and is given in% values.
  • the overall rating of the spot test is the sum of the four individual percentages. Products with poor soot dispersion give overall ratings of approx. 70% and lower, products with good soot dispersion give overall ratings of ⁇ 130%.
  • the PAMA comb polymers listed in Table 3 show good effectiveness both in the T / W test and in the soot spot test. Comparable linear PAMA copolymers with the same gross composition give a good rating in the soot test, but show no interfacial activity in the T / W test.

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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)
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
DE19518786A DE19518786A1 (de) 1995-05-22 1995-05-22 Schmierstoffadditive
DE19518786 1995-05-22

Publications (3)

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

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Application Number Title Priority Date Filing Date
EP96107578A Expired - Lifetime EP0744457B1 (fr) 1995-05-22 1996-05-13 Additif pour lubrifiants

Country Status (6)

Country Link
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 (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1788066A3 (fr) * 2005-11-22 2008-01-02 Rohm and Haas Company Lubrifiant synthetique à base de polymère acrylique
WO2017194654A1 (fr) 2016-05-13 2017-11-16 Evonik Oil Additives Gmbh Copolymères greffés à base d'un squelette de polyoléfine et de chaînes latérales de méthacrylate
EP3839018A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP3839017A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP3839019A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP4509584A1 (fr) 2023-07-20 2025-02-19 Infineum International Limited Compositions lubrifiantes à viscosité d'huile plate

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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
US6746993B2 (en) * 2001-04-06 2004-06-08 Sanyo Chemical Industries, Ltd. Viscosity index improver and lube oil containing the same
DE102005015931A1 (de) * 2005-04-06 2006-10-12 Rohmax Additives Gmbh Polyalkyl(meth) acrylat-Copolymere mit hervorragenden Eigenschaften
DE102009001446A1 (de) * 2009-03-10 2010-09-23 Evonik Rohmax Additives Gmbh Verwendung von Kammpolymeren als Antifatigue-Additive
US8143201B2 (en) * 2010-03-09 2012-03-27 Infineum International Limited Morpholine derivatives as ashless TBN sources and lubricating oil compositions containing same
JP2012188583A (ja) * 2011-03-11 2012-10-04 Sanyo Chem Ind Ltd 粘度指数向上剤及び潤滑油組成物
JP5797543B2 (ja) * 2011-12-21 2015-10-21 三洋化成工業株式会社 粘度指数向上剤及び潤滑油組成物
JP2013147608A (ja) * 2012-01-23 2013-08-01 Sanyo Chem Ind Ltd 粘度指数向上剤及び潤滑油組成物
JP2014080537A (ja) * 2012-10-18 2014-05-08 Sanyo Chem Ind Ltd 粘度指数向上剤及び潤滑油組成物
EP3272844B1 (fr) 2015-03-20 2021-06-16 Idemitsu Kosan Co.,Ltd. Additif améliorant l'indice de viscosité, composition lubrifiante et procédé de production de composition lubrifiante
KR101816427B1 (ko) * 2016-08-01 2018-01-08 현대자동차주식회사 연비 및 내구향상형 무단변속기오일 조성물
US10544241B2 (en) 2016-09-15 2020-01-28 Fina Technology, Inc. Farnesene-based macromonomers and methods of making and using the same
RU2019121715A (ru) * 2016-12-19 2021-01-19 Эвоник Оперейшнс Гмбх Комопозиция смазочного масла, содержащая диспергирующие гребенчатые полимеры
KR102587267B1 (ko) * 2018-01-23 2023-10-11 에보닉 오퍼레이션스 게엠베하 중합체-무기 나노입자 조성물, 이의 제조 방법 및 윤활제 첨가제로서의 이들의 용도
KR20220158221A (ko) * 2020-03-25 2022-11-30 도요보 가부시키가이샤 폴리아미드 수지 조성물
JP7663156B2 (ja) * 2022-09-09 2025-04-16 三菱ケミカル株式会社 重合体、潤滑油用摩擦低減剤、および潤滑油組成物
EP4585625A4 (fr) * 2022-09-09 2025-12-17 Mitsubishi Chem Corp Polymère, réducteur de frottement pour huile lubrifiante et composition d'huile lubrifiante

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US4985160A (en) * 1989-02-08 1991-01-15 E. I. Du Pont De Nemours And Company Branched polymers as fuel oil additives
DE3930142A1 (de) * 1989-09-09 1991-03-21 Roehm Gmbh Dispergierwirksame viskositaets-index-verbesserer
DE4121811A1 (de) * 1991-07-02 1993-01-07 Roehm Gmbh Verfahren zur herstellung von polyalkylmethacrylat-makromonomeren und ihre verwendung zur herstellung von kammpolymeren
DE4309853A1 (de) * 1993-03-26 1994-09-29 Roehm Gmbh Thermoplastisch verarbeitbare Elastomere mit verbesserten optischen Eigenschaften
DE4312715A1 (de) * 1993-04-20 1994-10-27 Roehm Gmbh Kammpolymere
US5312884A (en) * 1993-04-30 1994-05-17 Rohm And Haas Company Copolymer useful as a pour point depressant for a lubricating oil
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
DE19506399A1 (de) * 1995-02-24 1996-08-29 Roehm Gmbh Pfropfpolymere mit Emulgatoreigenschaften
DE19518786A1 (de) * 1995-05-22 1996-11-28 Roehm Gmbh Schmierstoffadditive

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1788066A3 (fr) * 2005-11-22 2008-01-02 Rohm and Haas Company Lubrifiant synthetique à base de polymère acrylique
WO2017194654A1 (fr) 2016-05-13 2017-11-16 Evonik Oil Additives Gmbh Copolymères greffés à base d'un squelette de polyoléfine et de chaînes latérales de méthacrylate
US10385288B1 (en) 2016-05-13 2019-08-20 Evonik Oil Additives Gmbh Graft copolymers based on polyolefin backbone and methacrylate side chains
EP3839018A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP3839017A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP3839019A1 (fr) 2019-12-16 2021-06-23 Infineum International Limited Modificateurs de viscosité de polymères en peigne à indice de viscosité élevé et procédés de modification de la viscosité de lubrifiant l'utilisant
EP4509584A1 (fr) 2023-07-20 2025-02-19 Infineum International Limited Compositions lubrifiantes à viscosité d'huile plate

Also Published As

Publication number Publication date
JPH08311133A (ja) 1996-11-26
EP0744457B1 (fr) 2003-09-24
SG54334A1 (en) 1998-11-16
US5756433A (en) 1998-05-26
JP2008255359A (ja) 2008-10-23
JP4142121B2 (ja) 2008-08-27
EP0744457A3 (fr) 1997-09-24
DE19518786A1 (de) 1996-11-28
DE59610726D1 (de) 2003-10-30
ATE250659T1 (de) 2003-10-15

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