EP3705557A1 - Verwendung von polymeren als zusätze für schmierölzusammensetzungen - Google Patents

Verwendung von polymeren als zusätze für schmierölzusammensetzungen Download PDF

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Publication number
EP3705557A1
EP3705557A1 EP19161442.9A EP19161442A EP3705557A1 EP 3705557 A1 EP3705557 A1 EP 3705557A1 EP 19161442 A EP19161442 A EP 19161442A EP 3705557 A1 EP3705557 A1 EP 3705557A1
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EP
European Patent Office
Prior art keywords
building blocks
polymer
use according
weight
lubricant oil
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.)
Withdrawn
Application number
EP19161442.9A
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English (en)
French (fr)
Inventor
Albert BODDIEN
Petra KÖSTER
Sabine Scherf
Steffi FANDRICH
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sasol Performance Chemicals GmbH
Original Assignee
Sasol Performance Chemicals GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sasol Performance Chemicals GmbH filed Critical Sasol Performance Chemicals GmbH
Priority to EP19161442.9A priority Critical patent/EP3705557A1/de
Priority to CN202080019113.XA priority patent/CN113544242A/zh
Priority to PCT/EP2020/056278 priority patent/WO2020178460A1/en
Priority to EP20707685.2A priority patent/EP3935145A1/de
Publication of EP3705557A1 publication Critical patent/EP3705557A1/de
Withdrawn legal-status Critical Current

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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
    • C10M145/16—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 polycarboxylic
    • 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
    • C10M2205/04—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing aromatic monomers, e.g. styrene
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/04—Molecular weight; Molecular weight distribution
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/069—Linear chain compounds
    • 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
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/52—Base number [TBN]
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/68—Shear stability
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines

Definitions

  • the present invention is concerned with the use of polymers as additives for lubricant oil compositions, wherein the polymers comprise styrene and maleic acid dialkyl ester building blocks and increase the shear stability of the compositions.
  • VI index index improvers VII
  • VII-treated lubricants are categorized as multigrade oils as opposed to monograde oils which contain no VII.
  • Polymer containing fluids exhibit less reduction in viscosity with increase in temperature than the corresponding base fluids containing no polymer.
  • the hydrodynamic volume of the polymer in the fluid increases with increase in temperature thereby resulting in an increase in viscosity, which greatly compensates the opposing effect of commonly observed reduction in viscosity of a fluid with rise in temperature.
  • the shear stability of the additive has strong influence on multigrade engine oil's ability to retain its viscosity under shearing conditions, experienced by the lubricant while in use.
  • the loss of viscosity of a lubricant under shear can be of two kinds, namely a temporary viscosity loss or a permanent viscosity loss.
  • One of the major problems with many of the VII is their tendency to undergo permanent reduction of viscosity as a result of mechanical shearing which occurs in most of the mechanical system.
  • Lubricant oil compositions have increased in recent years and will increase even further due to more demanding environmental and governmental standards.
  • Many functional fluids like hydraulic oils, gear oils, transmission oils and crankcase oils comprise VII and/or pour point depressants (PPD) in order to maintain a certain viscosity and flowability over a wide temperature regime.
  • PPD pour point depressants
  • Those additives are marketed based upon features such as cold temperature deposit control, stable viscosity and fluid durability. While VII improve the viscosity index of a lubricant oil, PPDs are applied to maintain low temperature flowability (pour point) and cold filterability (cold filter plugging point).
  • the polymers are usually based on polyolefins and polymethacrylates, acrylates or styrene-maleic anhydride co-polymers and esterified derivatives thereof. These polymers can be altered in their structures by using different alcohols for their production. Especially, poly(alkylmethacrylates) (PAMA) and poly-styrene-maleic anhydrides (PSMA) represent a class of VII or PPD which have been used for many years in lubricant oil compositions.
  • PAMA poly(alkylmethacrylates)
  • PSMA poly-styrene-maleic anhydrides
  • Base oils are produced by means of refining crude oils via distillation. While the lighter oils are used for fuels, the heavier cuts are suitable as base oils. By hydroprocessing sulfur and aromatics are removed using hydrogen under high pressure in order to obtain, purified base oils, which are desired when quality requirements are particularly stringent. Depending on the properties and the refining methods, base oils can be classified into 5 groups according to the American Petroleum Institute (API).
  • API American Petroleum Institute
  • API defines group I as "base stocks contain less than 90 percent saturates and/or greater than 0.03 percent sulfur and have a viscosity index greater than or equal to 80 and less than 120".
  • API defines group II as "base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulfur and have a viscosity index greater than or equal to 80 and less than 120".
  • API defines group III as "base stocks contain greater than or equal to 90 percent saturates and less than or equal to 0.03 percent sulfur and have a viscosity index greater than or equal to 120". This group may be described as synthetic technology oils or hydro-cracked synthetic oil.
  • Consists of synthetic oils made of Poly-alpha-olefins PAO are much more stable in extreme temperatures, which make them suitable for use in very cold weather (as found in northern Europe) as well as very hot weather (as in Middle East).
  • Group V oils include, among others, naphthenic oils and esters.
  • Industrial lubricants and base oils are further often classified according to the ISO 3448 viscosity grade classification.
  • the mid-point viscosity at 40 °C (mm 2 /s) represents the viscosity grade, respectively.
  • the range comprise classes from ISO VG 2 (1.98 - 2.42 mm 2 /s at 40 °C) to ISO VG 1500 class (1350 - 1650 mm 2 /s at 40 °C).
  • US2570846 A discloses the use of esters of styrene/maleic acid-copolymers to reduce the pour point and to increase the viscosity index of lubricating oils.
  • the alcohol moieties are based on linear C6- to C18- alkanols.
  • US3574575 A discloses esters of styrene/maleic acid-copolymers as fluidity improvers in liquid hydrocarbons.
  • the alcohol moieties of the ester groups are based on alcohols having at least 20 carbon atoms in the alkyl portion.
  • US5703023 A discloses polymeric viscosity index improvers made from styrene/maleic anhydride copolymers esterified with C8- to C18- alcohols, of which 50-90% are linear and the balance being branched (preferably 2-ethylhexanol).
  • US8293689 B2 discloses lubricating compositions containing styrene/maleic anhydride copolymers esterified with 2-decyltetradecanol (Isofol24) or 2-ethylhexanol and linear C12-15-alcohols (Neodol25) further comprising an anti-wear agent.
  • paraffin-containing fluids have a much higher viscosity and are mostly crude oils, whereas base oils are already refined fractions, from which the long-chain paraffins (wax) have been removed by dewaxing steps (see above).
  • the efficiency of depressing the pour point in crude oils is greatly influenced by the side chains of the polymer, respectively their carbon chain length and branching.
  • the pour point is determined by ASTM D5985 and mainly caused by the precipitation of wax crystals in the liquid, whereas in base oils much shorter alkanes tend to pour out and the pour point is determined according to ASTM D97. Therefore, the pour point of crude oils is usually at much higher temperatures than the one of base oils.
  • WO2017/012716 A1 teaches away from using the polymer additives in base oils.
  • shear stability does not play any role for additives that are exclusively pour point depressants.
  • the object of the present invention is to provide a polymer as an additive for use as shear stable viscosity index improvers with a high thickening efficiency and at the same time increased low temperature performance (pour point).
  • polystyrene-maleic anhydride (PSMA) based copolymers having linear alkyl and branched alkyl moieties, in particular 2-alkyl branched, generate high shear stable polymers with high thickening efficiency and increased low temperature performance (pour point) in a lubricant oil composition.
  • PSMA polystyrene-maleic anhydride
  • the present invention relates to the use of styrene-maleic acid dialkyl ester polymers in lubricant oil compositions.
  • the invention relates to the use of styrene-maleic acid alkyl ester polymers, where the ester groups are made from mixtures of long-chain linear and branched fatty alcohols.
  • the styrene-maleic acid alkyl ester polymers comprise at least the following building blocks: wherein
  • the branched alkyl groups R1, R2 are preferably branched at the 2 position and also independent thereof the branched alkyl groups have 12 to 26, more preferably 12 to 20, carbon atoms.
  • the linear alkyl groups R1, R2 have 12 to 20, more preferably 12 to 14, carbon atoms.
  • the polymer preferably has an acid value of less than 2 mg KOH/g, measured according to DIN EN 14104.
  • the polymer chain preferably comprises in total 50 to 150 building blocks a) and b) per polymer chain plus optionally other building blocks or end groups.
  • the polydispersity index (PDI) M w /M n thereof preferably is between 2 and 3. Both are determined by gel permeation chromatography (GPC).
  • the styrene-maleic acid dialkyl ester polymers preferably have a molecular weight Mw in the range of 40,000 to 52,000 g/mol.
  • the lubricant oil composition of the present invention is a composition comprising at least one base oil and at least one styrene-maleic acid dialkyl ester polymer as defined herein.
  • the lubricant oil composition may comprise further additives customary in the lubricant industry such as thickeners, antioxidants, antiwear agents, anticorrosives, metal deactivators, detergents, dyes, lubricity improvers, friction modifiers and high-pressure additives.
  • the base oil can be a mineral oil or a synthetic oil.
  • the base oil may have a kinematic viscosity of 20 to 2500 mm 2 /s, in particular of 40 to 500 mm 2 /s, at 40°C.
  • the base oil is at least one Group I-V base oil, preferably Group I-IV base oil, as well as mixtures thereof.
  • the base oil may also be at least one oil with a viscosity class according to ISO 3448 in the range of VG10 to VG320, preferably VG15 to VG68.
  • the base oil may have a pour point according to ASTM D97 equal to or below -10° C.
  • the polymers defined above are used to improve the Permanent Shear Stability Index (PSSI) of the lubricant oil composition at 100° C after 20 h to a value below 40%, preferably below 30%.
  • PSSI Permanent Shear Stability Index
  • the polymer may also increase the permanent shear stability of the lubricant oil composition and/or act as viscosity index improver and/or pour point depressant therein.
  • the polymers used are not uniform compounds but a mixture of compounds comprising above building blocks a) and b) and in so far above values refer to a mixture of compounds or in other words the overall composition of the polymers is defined by above values.
  • the polymer may comprise building blocks other than a) or b), for example maleic acid anhydride, or maleic acid mono-esters.
  • the building blocks can also have a random distribution or a block structure. R1 and R2 may be different for each b.
  • reaction scheme below illustrates the synthesis of styrene-maleic acid dialkyl ester polymers with an alternating structure.
  • the product can also be synthesized via alternative synthetic pathways (such as performing the esterification of maleic anhydride before copolymerising with styrene).
  • the styrene-maleic anhydride copolymer is then esterified as follows:
  • the completion of the polymerization to the desired level was measured by the acid number of the unreacted maleic anhydride in the filtered polymerisation solution.
  • the acid value is preferably less than 2 mg KOH/g.
  • the copolymer average molecular weight (mass) Mw was determined by using GPC analysis (MZGel SDplus 100 ⁇ 5 ⁇ m 300x8 mm/ MZ-Gel SDplus 1000 ⁇ 5 ⁇ m 300x8mm/Agilent polyPore 5 ⁇ m 300x7.5 mm equipped with a pre-column Mz-Gel SDplus linear 5 ⁇ m 20 50x8mm, injection volume 20 ⁇ L, solvent THF, flow rate 1 ml/min, detection via UV (254 nm) and refractive index) and was 20,000 g/mol.
  • Methane sulfonic acid (0.13 mol) was charged as catalyst and the reactor was heated up until the reflux of xylene started. The esterification reaction was carried out until the theoretical amount of water was collected.
  • the polystyrene-maleic anhydride copolymer ester solution was treated with activated carbon and filtrated before removal of xylene. Xylene was removed by distillation to obtain the neat copolymer ester.
  • Table 1 Typical analysis of long chain fatty alcohols used for preparation of the styrene m copolymer esters maleic in [wt.%] ISOFOL 12 ISOFOL 16 ISOFOL 20 ISOFOL 24 ISOFOL 2426S NAFOL 1214 NAFOL 1620 Chemical description 2-buty-octanol 2-hexyldecanol 2-octyl-decanol 2-decyltetradecanol Branched Alcohols, C24-26 Alcohols, C12-14 Alcohols, C16-20 [wt.%] [wt.%] [wt.%] [wt.%] [wt.%] [wt.%] [wt.%] [wt.%] C10 OH 1.5 max.
  • NAFOL 1214 refers to a C12-14 synthetic linear alcohol mixture
  • NAFOL 1620 refers to a C16-20 synthetic linear alcohol mixture
  • NAFOL 1218 refers to a C12-18 synthetic linear alcohol mixture.
  • the number of carbon atoms given above refers to the complete molecule and not only to the backbone of the alcohol.
  • Table 2 Selected properties of the polymeric additives evaluated Polymer PSMA-1214 * PSMA-1214/I12 (70/30) PSMA-1214/I16 (70/30) PSMA-1214/I20 (70/30) Alcohol NAFOL 1214 70% NAFOL 1214 70% NAFOL 1214 30% ISOFOL 12 30% ISOFOL 16 30% ISOFOL 20 Mw[g/mol] 48,492 46,502 48,280 41,798 PDI 1.83 1.93 1.94 2.03 Acid value [mg KOH/g] 1.69 1.72 1.14 1.18 % esterified COOH 96.9 96.9 97.9 97.8 Polymer PSMA-1214/124 (70/30) PSMA-1214/I2426S (70/30) PAMA-1214** PAMA-1214/1620** Alcohol 70% NAFOL 1214 70% NAFOL 1214 NAFOL 1214 70% NAFOL 1214 30%ISOFOL 24 30%ISOF
  • the polymers as defined in claim 1 improve the pour point depression, thickening efficiency and the viscosity index compared to existing PAMA-additives or PSMA with only linear alkyl chains.
  • PSSI Permanent Shear Stability Index
  • the 20h shear stability of the inventive PSMA based polymeric additive is higher than the PSMA based polymeric additives of the state of the art and at least in the same range as PAMA based ones. It has been surprisingly found that introducing a Guerbet structured alcohol in the PSMA-polymer led to improved shear stability.

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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)
EP19161442.9A 2019-03-07 2019-03-07 Verwendung von polymeren als zusätze für schmierölzusammensetzungen Withdrawn EP3705557A1 (de)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP19161442.9A EP3705557A1 (de) 2019-03-07 2019-03-07 Verwendung von polymeren als zusätze für schmierölzusammensetzungen
CN202080019113.XA CN113544242A (zh) 2019-03-07 2020-03-09 聚合物作为润滑油组合物的添加剂的用途
PCT/EP2020/056278 WO2020178460A1 (en) 2019-03-07 2020-03-09 Use of polymers as additives for lubricant oil compositions
EP20707685.2A EP3935145A1 (de) 2019-03-07 2020-03-09 Verwendung von polymeren als zusätze für schmierölzusammensetzungen

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19161442.9A EP3705557A1 (de) 2019-03-07 2019-03-07 Verwendung von polymeren als zusätze für schmierölzusammensetzungen

Publications (1)

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EP3705557A1 true EP3705557A1 (de) 2020-09-09

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EP19161442.9A Withdrawn EP3705557A1 (de) 2019-03-07 2019-03-07 Verwendung von polymeren als zusätze für schmierölzusammensetzungen
EP20707685.2A Withdrawn EP3935145A1 (de) 2019-03-07 2020-03-09 Verwendung von polymeren als zusätze für schmierölzusammensetzungen

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EP (2) EP3705557A1 (de)
CN (1) CN113544242A (de)
WO (1) WO2020178460A1 (de)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2570846A (en) 1947-03-20 1951-10-09 Socony Vacuum Oil Co Inc Mineral oil compositions containing esters of reaction product of maleic anhydride and styrene
US3574575A (en) 1969-04-21 1971-04-13 Mobil Oil Corp Liquid hydrocarbon oil compositions containing esters of styrene-maleic anhydride copolymers as fluidity improvers
US5703023A (en) 1991-12-24 1997-12-30 Ethyl Corporation Lubricants with enhanced low temperature properties
US8293689B2 (en) 2006-05-08 2012-10-23 The Lubrizol Corporation Lubricating composition containing a polymer and antiwear agents
US8343900B2 (en) 2006-05-08 2013-01-01 The Lubrizol Corporation Polymers and methods of controlling viscosity
EP3121204A1 (de) * 2015-07-23 2017-01-25 Sasol Performance Chemicals GmbH Polymeradditive für paraffinhaltige flüssigkeiten

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1275403C (en) * 1985-06-07 1990-10-23 Albert Rossi Lubricating oil composition containing dual additive combination for lowtemperature viscosity improvement
US6013735A (en) * 1998-02-13 2000-01-11 Ethyl Corporation Process for the preparation of acrylate and methacrylate polymers
AU767028B2 (en) * 1999-07-09 2003-10-30 Lubrizol Corporation, The Nitrogen-containing esterified carboxy-containing interpolymers having enhanced oxidative stability and lubricants containing them
US6475963B1 (en) * 2001-05-01 2002-11-05 Infineum International Ltd. Carboxylate-vinyl ester copolymer blend compositions for lubricating oil flow improvement
DE102005031244A1 (de) * 2005-07-01 2007-02-15 Rohmax Additives Gmbh Öllösliche Kammpolymere
US20150232781A1 (en) * 2012-08-20 2015-08-20 The Lubrizol Corporation Lubricating Composition Including Esterified Copolymer And Method
JP2014169426A (ja) * 2013-03-05 2014-09-18 Sanyo Chem Ind Ltd 粘度指数向上剤及びこれを含む潤滑油組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2570846A (en) 1947-03-20 1951-10-09 Socony Vacuum Oil Co Inc Mineral oil compositions containing esters of reaction product of maleic anhydride and styrene
US3574575A (en) 1969-04-21 1971-04-13 Mobil Oil Corp Liquid hydrocarbon oil compositions containing esters of styrene-maleic anhydride copolymers as fluidity improvers
US5703023A (en) 1991-12-24 1997-12-30 Ethyl Corporation Lubricants with enhanced low temperature properties
US8293689B2 (en) 2006-05-08 2012-10-23 The Lubrizol Corporation Lubricating composition containing a polymer and antiwear agents
US8343900B2 (en) 2006-05-08 2013-01-01 The Lubrizol Corporation Polymers and methods of controlling viscosity
EP3121204A1 (de) * 2015-07-23 2017-01-25 Sasol Performance Chemicals GmbH Polymeradditive für paraffinhaltige flüssigkeiten
WO2017012716A1 (en) 2015-07-23 2017-01-26 Sasol Performance Chemicals Gmbh Use of polymeric additives for paraffin-containing fluids

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EP3935145A1 (de) 2022-01-12
WO2020178460A1 (en) 2020-09-10
CN113544242A (zh) 2021-10-22

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