EP0438709A1 - Motorenöl mit einem Gehalt an Phenolalkoxylaten - Google Patents

Motorenöl mit einem Gehalt an Phenolalkoxylaten Download PDF

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Publication number
EP0438709A1
EP0438709A1 EP90124070A EP90124070A EP0438709A1 EP 0438709 A1 EP0438709 A1 EP 0438709A1 EP 90124070 A EP90124070 A EP 90124070A EP 90124070 A EP90124070 A EP 90124070A EP 0438709 A1 EP0438709 A1 EP 0438709A1
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Prior art keywords
oxide
bisphenol
motor
butylene oxide
motor oil
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EP90124070A
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French (fr)
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EP0438709B1 (de
Inventor
Helmut Dr. Mach
Helmut Schmidt
Knut Dr. Oppenlaender
Roland Dr. Schwen
Jürgen Dr. Mohr
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BASF SE
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BASF SE
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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
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/18—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/24—Polyethers
    • C10M145/26—Polyoxyalkylenes
    • C10M145/36—Polyoxyalkylenes etherified
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10M169/04—Mixtures of base-materials and additives
    • C10M169/041—Mixtures of base-materials and additives the additives being macromolecular compounds only
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/102—Aliphatic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
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    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/283—Esters of polyhydroxy compounds
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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Definitions

  • the invention relates to engine oils containing phenol-started oil-soluble polyethers to improve the piston cleanliness of motor vehicle engines.
  • Modern lubricants are subject to increasing demands with regard to reducing wear, longer running times, reduced deposits, engine cleanliness and low-temperature properties. Since there are quantitative limits to the use of additives, the amount of ash formers (detergents) for gasoline engine oils must not exceed certain values, the proportion of wear protection (zinc dithiophosphates) is limited due to the three-way catalysts and dirt dispersers can attack the rubber sealing elements if the dose is too high. Attempts have been made to improve the performance of the motor oil by using new base oils. It was therefore the object of the invention to provide new engine oil components which bring about a significantly increased performance compared to the prior art.
  • R 2 O is derived from a mixture of butylene oxide and propylene oxide with a maximum of 80% by weight of propylene oxide and preferably from butylene oxide alone.
  • the phenol component is alkylated with 1 or 2 alkyl radicals having 6 to 24, preferably 9 to 12 carbon atoms or consists of a bisphenol.
  • the phenol alkoxylates mentioned are obtained in a manner known per se by alkoxylation of the phenols with butylene oxide or mixtures of butylene oxide and propylene oxide with alkali.
  • Butylene oxide alone in amounts of 5 to 25 mol / phenol group is particularly preferred.
  • Dodecylphenol, nonylphenol and bisphenol A are particularly suitable as alkylphenols.
  • Preparation example (general) Reaction of alkylphenol or bisphenol A with alkylene oxides
  • 0.1% by weight of KOH, finely pulverized, based on the entire batch are distributed in the alkylphenol with stirring and heated to 130 ° C. at 200 mbar. Remaining traces of water are removed.
  • the autoclave is then closed and alkylene oxide is metered in so that a pressure of 6 bar is not exceeded.
  • Different alkylene oxides can be metered in simultaneously or in succession, so that statistical polyethers or blocks are formed with more or less sharp transitions. After the alkylene oxides have run in, the pressure drops to 2 to 3 bar in the course of 3 to 10 h.
  • the mixture is cooled to 80 ° C. and relaxed via a membrane valve and evacuated to 20 to 30 mbar. After maintaining the reduced pressure for about 1 h, equivalent amounts of acidic ion exchanger are then added to remove potassium and the mixture is filtered.
  • Motor oils are liquids, based on selected base oils, to which additives are added to achieve special properties in the motor. These are e.g. Engine cleanliness, reduced deposits, high temperature resistance, reduced wear and longer running time (cf. Aral oil guide, 10th edition 1989.1, pp. 23-30, and 1989.2, pp. 4-9).
  • alkylphenoxylates to be used according to the invention are added to motor oils, especially those based on hydrocarbons, in amounts of up to 10%, in particular 1 to 8% by weight.
  • a representative engine oil blend contains, for example, the following essential components 80 to 95 wt .-% base oil components 0.5 to 2.5% by weight viscosity index improver (100%) 1.5 to 10% by weight of ashless dispersants 1.5 to 8 wt% detergent 20.5 to 6% by weight wear protection 1 to 8% by weight of the phenoxylates to be added according to the invention
  • the alkylphenoxylates to be used according to the invention have a significantly higher temperature stability (DTG) than conventional alkoxylates.
  • the temperature stability with very good lubricating performance of the alkylphenoxylates to be used according to the invention is particularly evident in the test in the engine of motor vehicles.
  • a motor oil of the higher performance class API SF / CD was chosen as the basis for the test, to which 5% alkylphenoxylate was added in each case.
  • the engine suitability was tested. It was surprisingly found that the motor oils with 5% of the alkylphenoxylates to be used according to the invention with performance ratings of up to 79 points (i.e. very good ratings) were significantly higher than the starting engine oil API SF / CD with 67 or 69 (table).
  • Alkoxylates eg started with tridekanol and 1-butene oxide as alkylene oxide did not improve the engine test results.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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Abstract

Motorenöle enthaltend bis zu 10 Gew.-% einer Grundölkomponente, die aus einem Umsetzungsprodukt eines Alkylphenols oder Bisphenol A mit Butylenoxid oder Butylenoxid/Propylenoxid besteht. Die Motorenöle haben eine verbesserte Hitzestabilität und bewirken eine größere Kolbensauberkeit.

Description

  • Die Erfindung betrifft Motorenöle mit einem Gehalt an phenolgestarteten öllöslichen Polyethern zur Verbesserung der Kolbensauberkeit von Kfz-Motoren.
  • An moderne Schmiermittel (Motorenöle) werden zunehmend höhere Anforderungen hinsichtlich Verringerung des Verschleißes, höherer Laufzeiten, Ablagerungsverminderung, Motorensauberkeit und Tieftemperatureigenschaften gestellt. Da der Verwendung von Additiven mengenmäßig Grenzen gesetzt sind, die Menge an Aschebildnern (Detergents) für Ottomotorenöle bestimmte Werte nicht überschreiten darf, der Anteil an Verschleißschutz (Zinkdithiophosphaten) wegen der Dreiwegekatalysatoren begrenzt ist und Schmutzdispergatoren bei zu hoher Dosis die Dichtelemente aus Kautschuk angreifen können, wurde versucht, durch neuartige Grundöle die Leistungsfähigkeit des Motorenöles zu verbessern. Es war daher die Aufgabe der Erfindung neue Motorenölkomponenten zur Verfügung zu stellen, die eine zum Stand der Technik deutlich erhöhte Leistungsfähigkeit bewirken.
  • Diese Aufgabe wurde gelöst mit Motorenölen, die als Grundölkomponente bis zu 10 Gew.-% eines Alkylphenolalkoxylats der Formel

    R1-[O-(R²-O) n H] m
    Figure imgb0001

    enthalten, in der R¹ den Rest eines Alkylphenols mit bis zu 2 Alkylresten mit 6 bis 24 C-Atomen oder eines Bisphenols, R² den Rest von Butylenoxid allein oder im Gemisch mit Propylenoxid, n die Zahlen 5 bis 100 und m 1 und 2 bedeuten.
  • Nach einer bevorzugten Ausführungsform der Erfindung verwendet man solche Verbindungen der genannten Formel in der R²O sich von einem Gemisch aus Butylenoxid und Propylenoxid mit maximal 80 Gew.-% Propylenoxid und vorzugsweise von Butylenoxid allein ableitet.
  • Die Phenolkomponente ist mit 1 oder 2 Alkylresten mit 6 bis 24, vorzugsweise 9 bis 12 C-Atomen alkyliert oder besteht aus einem Bisphenol.
  • Die genannten Phenolalkoxylate werden in an sich bekannter Weise durch Alkoxylierung der Phenole mit Butylenoxid oder Mischungen aus Butylenoxid und Propylenoxid mit Alkali erhalten.
  • Die Umsetzung des Phenols mit Butylenoxid, mit Butylenoxid und Propylenoxid im Gemisch oder nacheinander in beliebiger Reihenfolge erfolgt so, daß insgesamt 5 bis 100 Mol, vorzugsweise 10 bis 50 Mol Alkylenoxid pro OH-Gruppe des Phenols umgesetzt werden.
  • Butylenoxid allein in Mengen von 5 bis 25 Mol/Phenolgruppe ist besonders bevorzugt.
  • Als Alkylphenole kommen im einzelnen Dodecylphenol, Nonylphenol und Bisphenol A in Betracht.
  • Im folgenden wird die Herstellung der Polyether im einzelnen erläutert.
    • Herstellungsbeispiel (allgemein) Umsetzung von Alkylphenol bzw. Bisphenol A mit Alkylenoxiden In einem Autoklaven mit Rührer werden bezogen auf den gesamten Ansatz 0,1 Gew.-% KOH fein pulverisiert im Alkylphenol unter Rühren verteilt und bei 200 mbar auf 130°C erhitzt. Dabei werden restliche Wasserspuren abgezogen. Dann wird der Autoklav geschlossen und Alkylenoxid so zudosiert, daß ein Druck von 6 bar nicht überschritten wird. Die Dosierung verschiedener Alkylenoxide kann gleichzeitig oder nacheinander erfolgen, so daß statistische Polyether oder Blöcke entstehen mit mehr oder minder scharfen übergängen. Nach Zulaufen der Alkylenoxide fällt der Druck im Verlauf von 3 bis 10 h auf 2 bis 3 bar. Ist dieser Druck erreicht, kühlt man auf 80°C und entspannt über ein Membranventil und evakuiert bis auf 20 bis 30 mbar. Nach Aufrechterhalten des verminderten Drucks für ca. 1 h setzt man dann äquivalente Mengen sauren Ionenaustauscher zur Entfernung von Kalium zu und filtriert.
  • Nach der vorstehend angegebenen Methode wurden folgende Produkte hergestellt:
    • A:
    Isononylphenol wird mit 1-Butenoxid im molaren Verhältnis 1 : 24 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 320 mm²/s bei 40°C und ein rechnerisches Molekulargewicht von 1848.
    B:
    Isononylphenol wird mit 1-Butenoxid im molaren Verhältnis 1 : 8 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 130 mm²/s bei 40°C und ein rechnerisches Molekulargewicht von 796.
    C:
    Isononylphenol wird mit 1-Butenoxid und Propenoxid im Verhältnis 1 : 12 : 12 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 125 mm²/s bei 40°C und ein rechnerisches Molekulargewicht von 1684.
    D:
    Nonylphenol wird mit Propenoxid im molaren Verhältnis 1 : 10 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 87 mm²/s bei 40°C und ein Molekulargewicht von 806.
    E:
    Bisphenol A wird mit Butenoxid im molaren Verhältnis 1 : 10 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 360 mm²/s bei 40°C und ein Molekulargewicht von 878.
    F:
    Bisphenol A wird mit Butenoxid im molaren Verhältnis 1 : 15 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 320 mm²/s bei 40°C und ein Molekulargewicht von 1238.
    G:
    Bisphenol A wird mit Butenoxid im molaren Verhältnis 1 : 25 umgesetzt. Der erhaltene Polyether hat eine Viskosität von 380 mm²/s bei 40°C und ein Molekulargewicht von 1958.
  • Motorenöle sind Flüssigkeiten, basierend auf ausgewählten Grundölen, denen Additive (Wirkstoffe) zugemischt werden, um im Motor spezielle Eigenschaften zu erzielen. Dies sind z.B. Motorensauberkeit, Ablagerungsverminderung, Hochtemperaturbeständigkeit, Verschleißreduzierung und längere Laufzeit (vgl. Ölfibel Aral, 10. Auflage 1989.1, S. 23-30, und 1989.2, S. 4-9).
  • Die erfindungsgemäß zu verwendenden Alkylphenoxylate werden Motorenölen, vor allem solchen auf Kohlenwasserstoffbasis in Mengen von bis zu 10 %, insbesondere 1 bis 8 Gew.-% zugesetzt.
  • Eine repräsentative Motorenölmischung enthält zum Beispiel folgende wesentlichen Bestandteile
    80 bis 95 Gew.-% Grundölkomponenten
    0,5 bis 2,5 Gew.-% Viskositätsindexverbesserer (100%ig)
    1,5 bis 10. Gew.-% Ashless dispersants
    1,5 bis 8 Gew.-% Detergents
    20,5 bis 6 Gew.-% Verschleißschutz
    1 bis 8 Gew.-% der erfindungsgemäß zuzusetzenden Phenoxylate
  • Die erfindungsgemäß zu verwendenden Alkylphenoxylate weisen gegenüber herkömmlichen Alkoxylaten eine deutlich höhere Temperaturstabilität auf (DTG).
  • Die Temperaturstabilität bei sehr guter Schmierleistung der erfindungsgemäß zu verwendenden Alkylphenoxylate erweist sich vor allem im Test im Triebwerk von Kfz-Motoren. Für die Testdurchführung wurde ein Motorenöl der gehobenen Leistungsklasse API SF/CD als Basis gewählt, dem jeweils 5 % Alkylphenoxylat zugesetzt wurde. Im MWM-Prüfdieselmotorentest Verfahren zur Prüfung der Kolbensauberkeit, Teil B, DIN 51361, CEC-L-12-A-76, wurde die motorische Eignung geprüft. Hierbei zeigte sich überraschenderweise, daß die Motorenöle mit 5 % der erfindungsgemäß zu verwendenden Alkylphenoxylate mit Leistungsbewertungen bis zu 79 Punkten (d.s. sehr gute Bewertungen) deutlich über dem Ausgangsmotorenöl API SF/CD mit 67 bzw. 69 lagen (Tabelle).
  • Alkoxylate z.B. mit Tridekanol gestartet und 1-Butenoxid als Alkylenoxid führten zu keiner Verbesserung der Motorentestergebnisse.
    Figure imgb0002

Claims (6)

  1. Motorenöl, bestehend aus Grundölkomponenten und Additiven enthaltend als Grundölkomponente bis zu 10 Gew.-% eines Alkylphenolalkoxylats der Formel



            R¹-[O-(R²-O)nH]m ,



    in der R¹ den Rest eines Alkylphenols mit bis zu 2 Alkylresten mit 6 bis 24 C-Atomen oder eines Bisphenols, R² den Rest von Butylenoxid allein oder im Gemisch mit Propylenoxid, n die Zahlen 5 bis 100 und m 1 und 2 bedeuten.
  2. Motorenöl nach Anspruch 1, dadurch gekennzeichnet, daß R²O sich von Butylenoxid ableitet.
  3. Motorenöl nach Anspruch 1, dadurch gekennzeichnet, daß R²O sich von einem Gemisch aus Propylenoxid und Butylenoxid mit maximal 80 Molprozent Propylenoxid ableitet.
  4. Motorenöl nach Anspruch 1, dadurch gekennzeichnet, daß als weitere Grundölkomponenten Mineralöl, Polyalphaolefin, Polyinternalolefin, Hydrocracköl, Dicarbonsäureester und Neopolyolester enthalten sind.
  5. Motorenöl nach Anspruch 1, dadurch gekennzeichnet, daß R¹ den Rest eines Mono- und Dialkylphenols mit 6 bis 24 C-Atomen im Alkylrest bedeutet.
  6. Motorenöl nach Anspruch 1, dadurch gekennzeichnet, daß R¹ den Rest des Bisphenols A bedeutet.
EP90124070A 1990-01-16 1990-12-13 Motorenöl mit einem Gehalt an Phenolalkoxylaten Expired - Lifetime EP0438709B1 (de)

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AT90124070T ATE88496T1 (de) 1990-01-16 1990-12-13 Motorenoel mit einem gehalt an phenolalkoxylaten.

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DE4001043A DE4001043A1 (de) 1990-01-16 1990-01-16 Motorenoel mit einem gehalt an phenolalkoxylaten
DE4001043 1990-01-16

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Cited By (8)

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WO2000023544A1 (en) * 1998-10-16 2000-04-27 Castrol Limited An engine oil comprising a polyalkylene glycol used in a direct injection engine
WO2000052117A1 (de) * 1999-03-04 2000-09-08 Rohmax Additives Gmbh Motorenölzusammensetzung mit reduzierter neigung zur bildung von ablagerungen
WO2008002598A2 (en) * 2006-06-27 2008-01-03 Exxonmobil Research And Engineering Company Synthetic phenolic ether lubricant base stocks and lubricating oils comprising such base stocks mixed with co-base stocks and/or additives
EP2456845A2 (de) * 2009-07-23 2012-05-30 Dow Global Technologies LLC Polyalkylenglykole als schmiermittelzusätze für gruppe i-iv-kohlenwasserstofföle
WO2013164449A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
WO2013164457A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
WO2014189712A1 (en) * 2013-05-23 2014-11-27 Dow Global Technologies Llc Oil soluble polyoxybutylene polymers as friction modifiers for lubricants
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition

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FR2968011B1 (fr) * 2010-11-26 2014-02-21 Total Raffinage Marketing Composition lubrifiante pour moteur
US9850447B2 (en) 2013-05-23 2017-12-26 Dow Global Technologies Llc Polyalkylene glycols useful as lubricant additives for hydrocarbon base oils

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US3696048A (en) * 1970-04-06 1972-10-03 Universal Oil Prod Co Corrosion inhibiting composition and use thereof
US3789003A (en) * 1971-08-25 1974-01-29 Texaco Inc Solubilizing process
GB2003920A (en) * 1977-08-12 1979-03-21 Kao Corp Composition for lubricating treatment of synthetic fibres
EP0246612A2 (de) * 1986-05-20 1987-11-25 Dai-Ichi Kogyo Seiyaku Co., Ltd. Schmierölzusammensetzung
EP0376236A1 (de) * 1988-12-29 1990-07-04 BASF Aktiengesellschaft Verwendung von Addukten von 1,2-Butylenoxid an Aminen als Schmierstoffe und Schmierstoffe, diese Addukte enthaltend

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US3328284A (en) * 1965-01-06 1967-06-27 Petrolite Corp Oxyalkylate-sulfonate hydrocarbon inhibitor
US3696048A (en) * 1970-04-06 1972-10-03 Universal Oil Prod Co Corrosion inhibiting composition and use thereof
US3789003A (en) * 1971-08-25 1974-01-29 Texaco Inc Solubilizing process
GB2003920A (en) * 1977-08-12 1979-03-21 Kao Corp Composition for lubricating treatment of synthetic fibres
EP0246612A2 (de) * 1986-05-20 1987-11-25 Dai-Ichi Kogyo Seiyaku Co., Ltd. Schmierölzusammensetzung
EP0376236A1 (de) * 1988-12-29 1990-07-04 BASF Aktiengesellschaft Verwendung von Addukten von 1,2-Butylenoxid an Aminen als Schmierstoffe und Schmierstoffe, diese Addukte enthaltend

Cited By (28)

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WO2000023544A1 (en) * 1998-10-16 2000-04-27 Castrol Limited An engine oil comprising a polyalkylene glycol used in a direct injection engine
WO2000052117A1 (de) * 1999-03-04 2000-09-08 Rohmax Additives Gmbh Motorenölzusammensetzung mit reduzierter neigung zur bildung von ablagerungen
US6458750B1 (en) 1999-03-04 2002-10-01 Rohmax Additives Gmbh Engine oil composition with reduced deposit-formation tendency
JP2002538266A (ja) * 1999-03-04 2002-11-12 ローマックス アディティヴス ゲゼルシャフト ミット ベシュレンクテル ハフツング 低い沈積物形成傾向を有するエンジンオイル組成物
WO2008002598A2 (en) * 2006-06-27 2008-01-03 Exxonmobil Research And Engineering Company Synthetic phenolic ether lubricant base stocks and lubricating oils comprising such base stocks mixed with co-base stocks and/or additives
WO2008002598A3 (en) * 2006-06-27 2008-05-15 Exxonmobil Res & Eng Co Synthetic phenolic ether lubricant base stocks and lubricating oils comprising such base stocks mixed with co-base stocks and/or additives
EP2456845A2 (de) * 2009-07-23 2012-05-30 Dow Global Technologies LLC Polyalkylenglykole als schmiermittelzusätze für gruppe i-iv-kohlenwasserstofföle
JP2013500358A (ja) * 2009-07-23 2013-01-07 ダウ グローバル テクノロジーズ エルエルシー グループｉ〜ｉｖの炭化水素油のための潤滑添加剤として有用なポリアルキレングリコール
EP2456845B2 (de) † 2009-07-23 2020-03-25 Dow Global Technologies LLC Polyalkylenglykole als schmiermittelzusätze für gruppe i-iv-kohlenwasserstofföle
EP2456845B1 (de) * 2009-07-23 2017-03-29 Dow Global Technologies LLC Polyalkylenglykole als schmiermittelzusätze für gruppe i-iv-kohlenwasserstofföle
KR20150020534A (ko) * 2012-05-04 2015-02-26 토탈 마케팅 서비스 엔진 윤활유 조성물
RU2635569C2 (ru) * 2012-05-04 2017-11-14 Тотал Маркетинг Сервисез Смазочная композиция для двигателя
CN111607451A (zh) * 2012-05-04 2020-09-01 道达尔销售服务公司 发动机润滑剂组合物
KR20150015455A (ko) * 2012-05-04 2015-02-10 토탈 마케팅 서비스 엔진용 윤활 조성물
FR2990215A1 (fr) * 2012-05-04 2013-11-08 Total Raffinage Marketing Composition lubrifiante pour moteur
JP2015516007A (ja) * 2012-05-04 2015-06-04 トータル・マーケティング・サービシーズ エンジン用潤滑剤組成物
JP2015516006A (ja) * 2012-05-04 2015-06-04 トータル・マーケティング・サービシーズ エンジン用潤滑剤組成物
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WO2013164457A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
FR2990213A1 (fr) * 2012-05-04 2013-11-08 Total Raffinage Marketing Composition lubrifiante pour moteur
RU2638542C2 (ru) * 2012-05-04 2017-12-14 Тотал Маркетинг Сервисез Смазочная композиция для двигателя
US10604717B2 (en) 2012-05-04 2020-03-31 Total Marketing Services Lubricant composition for an engine
WO2013164449A1 (fr) 2012-05-04 2013-11-07 Total Marketing Services Composition lubrifiante pour moteur
US10752858B2 (en) 2012-11-16 2020-08-25 Total Marketing Services Lubricant composition
CN105209583B (zh) * 2013-05-23 2018-05-04 陶氏环球技术有限责任公司 作为润滑剂的摩擦改进剂的油溶性聚氧化丁烯聚合物
US9914895B2 (en) 2013-05-23 2018-03-13 Dow Global Technologies Llc Oil soluble polyoxybutylene polymers as friction modifiers for lubricants
CN105209583A (zh) * 2013-05-23 2015-12-30 陶氏环球技术有限责任公司 作为润滑剂的摩擦改进剂的油溶性聚氧化丁烯聚合物
WO2014189712A1 (en) * 2013-05-23 2014-11-27 Dow Global Technologies Llc Oil soluble polyoxybutylene polymers as friction modifiers for lubricants

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CA2034144A1 (en) 1991-07-17
ATE88496T1 (de) 1993-05-15
EP0438709B1 (de) 1993-04-21
ES2042180T3 (es) 1993-12-01
DE4001043A1 (de) 1991-07-18
DE59001259D1 (de) 1993-05-27
CA2034144C (en) 1999-06-08

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