EP0758016B1 - Verwendung einer Schmiermittelzusammensetzung, enthaltend eine Mischung von Antioxidationsadditiven - Google Patents

Verwendung einer Schmiermittelzusammensetzung, enthaltend eine Mischung von Antioxidationsadditiven Download PDF

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Publication number
EP0758016B1
EP0758016B1 EP96305869A EP96305869A EP0758016B1 EP 0758016 B1 EP0758016 B1 EP 0758016B1 EP 96305869 A EP96305869 A EP 96305869A EP 96305869 A EP96305869 A EP 96305869A EP 0758016 B1 EP0758016 B1 EP 0758016B1
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Prior art keywords
boron
antioxidant
oils
aromatic amine
lubricant
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EP96305869A
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English (en)
French (fr)
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EP0758016A1 (de
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David Gary Lawton Esso Petroleum Co. Ltd. Holt
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ExxonMobil Technology and Engineering Co
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ExxonMobil Research and Engineering Co
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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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C—CHEMISTRY; METALLURGY
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/12—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/064—Di- and triaryl amines
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    • C10M2215/066—Arylene diamines
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    • C10M2215/067—Polyaryl amine alkanes
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    • C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2215/26—Amines
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    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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Definitions

  • This invention relates to lubricant compositions, especially for the lubrication of internal combustion engines, having improved antioxidant performance.
  • Engine oil lubricants contain a variety of performance enhancing additives including antioxidants and dispersants.
  • the antioxidants such as diphenylamines and hindered phenols, are present to prevent the oil from oxidising. They function by trapping radicals formed during oil usage, thus interrupting the chain reaction which leads to acid build-up and hence sludge formation.
  • the dispersants which typically consist of a polar head, such as a polyamine, attached to an inert, oil-soluble body, such as polyisobutene, function through the polar head binding to insoluble degradation products, thus suspending them in the oil.
  • the polyamine employed for this purpose is often aggressive to the fluorocarbon elastomer seals used in the engine. To alleviate this problem the polyamine is usually capped by boron; the more aggressive the polyamine the higher the required boron level of the dispersant.
  • GB-A-1271556 describes an antioxidant additive which is a mixture of (a) the reaction product of a boron compound with a long chain hydrocarbyl carboxylic acid or anhydride thereof with a primary or secondary amine, and (b) a polycyclic phenolic compound.
  • US-A-5354484 describes a lubricant additive which provides high temperature stability comprising a mixture of (i) an amine salt of a substituted phosphoric acid and (ii) an amine-substituted hydrocarbyl succinic acid compound.
  • EP-A-471120 describes the use of hindered phenolic/phosphoro-dithioate-derived alcohol borates as antioxidant and antiwear additive for lubricants and fuels.
  • the present invention provides the use of a boron-containing compound to enhance the antioxidant performance in an internal combustion engine of an aromatic amine antioxidant in a lubricant composition in which:
  • aromatic amine an amine compound wherein at least one nitrogen atom is bonded directly to at least one aryl moiety.
  • amine compound is of the formula: where
  • both R 1 and R 2 are aryl groups.
  • R 3 is hydrogen.
  • the aromatic antioxidant is a diarylamine compound.
  • aromatic antioxidants examples include phenylamine, diphenyl-amine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-[4-1,3-dimethylbutyl-phenyl]-amine, di-[4-(1,1,3,3-tetramethyl butyl)-phenyl]-amine, N-allyldiphenylamine, 4-isopropoxydiphenyl-amine and di-4-methoxyphenylamine.
  • aromatic antioxidants examples include phenylamine, diphenyl-amine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-[4-1,3-dimethylbutyl-phenyl]-amine, di-[4-(1,1,3,3-tetramethyl butyl)-phenyl]-amine, N-allyldiphenylamine, 4-isopropoxydiphenyl-amine
  • the ashless dispersant is most preferably a borated polyisobutene-succinic acid or anhydride (PIBSA) dispersant, especially the PIBSA - polyamine (PIBSA-PAM) compounds formed by the reaction of the PIBSA compound with an amine such as polyethylene amine, polyoxyethylene or a polyol amine.
  • PIBSA polyisobutene-succinic acid or anhydride
  • PAM PIBSA - polyamine
  • the dispersants may be borated using conventional techniques, for example by reacting the dispersant with a boron compound selected from, for example, boron oxide, boron halides, boron acids and esters of boron acids.
  • a boron compound selected from, for example, boron oxide, boron halides, boron acids and esters of boron acids.
  • the present invention provides a lubricant composition
  • a lubricant composition comprising a major amount of lubricating oil basestock and a minor amount of the boron/aromatic amine antioxidant combination as described above.
  • 'major amount' is meant greater than 50 wt.%, preferably from more than 50 to 98 wt.%, more preferably from 80 to 95.5 wt.%, the balance being made up of the boron/aromatic amine antioxidant combination and, optionally, other lubricant additives.
  • minor amount' is meant an amount that is sufficient to improve the antioxidant performance of the lubricant composition.
  • the amount of aromatic amine antioxidant contained in the lubricant composition is preferably from 0.01 to 5 wt.%, more preferably from 0.05 to 2 wt.%, and most preferably from 0.2 to 0.8 wt.% based on the total weight of the composition.
  • the amount of ashless borated dispersant referred to above is generally in the range from 0.5 to 15 wt.%, preferably from 1 to 10 wt.%, more preferably from 2 to 8 wt.%, based on the total weight of the composition.
  • the lubricating oil basestock can be derived from natural lubricating oils, synthetic lubricating oils, or mixtures thereof. Suitable lubricating oil basestocks include basestocks obtained by isomerization of synthetic wax and slack wax, as well as hydrocrackate basestocks produced by hydrocracking (rather than solvent extracting) the aromatic and polar components of the crude. In general, the lubricating oil basestock will have a kinematic viscosity ranging from about 2 to about 1,000 cSt at 40°C.
  • Natural lubricating oils include animal oils, vegetable oils (e.g., castor oils and lard oil), petroleum oils, mineral oils, and oils derived from coal or shale.
  • Synthetic oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as polymerized and interpolymerized olefins, alkylbenzenes, polyphenyls, alkylated diphenyl ethers, alkylated diphenyl ethers, alkylated diphenyl sulfides, as well as their derivatives, analogs, and homologs thereof, and the like.
  • Synthetic lubricating oils also include alkylene oxide polymers, interpolymers, copolymers and derivatives thereof wherein the terminal hydroxyl groups have been modified by esterification, etherification, etc.
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids with a variety of alcohols. Esters useful as synthetic oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers.
  • Silicon-based oils (such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxysiloxane oils and silicate oils) comprise another useful class of synthetic lubricating oils.
  • Other synthetic lubricating oils include liquid esters of phosphorus-containing acids, polymeric tetrahydro-furans, polyalphaolefins, and the like.
  • the lubricating oil may be derived from unrefined, refined, rerefined oils, or mixtures thereof.
  • Unrefined oils are obtained directly from a natural source or synthetic source (e.g., coal, shale, or tar sands bitumen) without further purification or treatment.
  • Examples of unrefined oils include a shale oil obtained directly from a retorting operation, a petroleum oil obtained directly from distillation, or an ester oil obtained directly from an esterification process, each of which is then used without further treatment.
  • Refined oils are similar to the unrefined oils except that refined oils have been treated in one or more purification steps to improve one or more properties.
  • Suitable purification techniques include distillation, hydro-treating, dewaxing, solvent extraction, acid or base extraction, filtration, and percolation, all of which are known to those skilled in the art.
  • Rerefined oils are obtained by treating refined oils in processes similar to those used to obtain the refined oils. These rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques for removal of spent additives and oil breakdown products.
  • the lubricant composition may also contain other additives such as detergents, dispersants, friction modifiers, antiwear agents, extreme pressure agents, other antioxidants, rust and corrosion inhibitors, pour point depressants, viscosity index improvers, antifoam agents, demulsifiers, and hydrolytic stabilisers.
  • additives are well known in the art, and are described, for example, in 'Lubricants and Related Products' by Dieter Klamann, Verlag Chemie, Weinheim, Germany 1984.
  • the lubricant composition according to the invention may be used in any suitable lubricating application which requires stability against lubricant oxidation. However, it is especially useful as an engine oil, for example in an internal combustion engine.
  • Engine oil formulations were blended as shown in Table 1 below. Each formulation contained mineral oil basestock, a conventional engine oil addpack, a conventional viscosity index (VI) improver, Irganox L57 - an alkyl-substituted diphenylamine antioxidant available from Ciba-Geigy Ltd., and a PIBSA-PAM dispersant available from Exxon Chemical Ltd. The boration level of the dispersant was varied from zero through to heavily borated.
  • VI viscosity index
  • Irganox L57 an alkyl-substituted diphenylamine antioxidant available from Ciba-Geigy Ltd.
  • PIBSA-PAM dispersant available from Exxon Chemical Ltd.
  • the boration level of the dispersant was varied from zero through to heavily borated.
  • Comparative formulations were also blended containing no diphenylamine antioxidant.

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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. Verwendung einer borhaltigen Verbindung zur Steigerung der Antioxidansleistung eines aromatischen Amin-Antioxidans in einer Schmierölzusammensetzung in einem Verbrennungsmotor, in der
    (a) das aromatische Amin-Antioxidans ausgewählt ist aus Phenylamin, Diphenylamin, Phenylnaphthylamin und Mischungen derselben, wobei die Verbindungen substituiert oder unsubstituiert sein können, und
    (b) die borhaltige Verbindung boriertes aschefreies Dispergiermittel ist, wobei das Dispergiermittel eine Polyisobutenbernsteinsäure, ein Polyisobutenbernsteinsäureanhydrid, ein Polyisobutenbernsteinsäure-Polyamin oder ein Polyisobutenbernsteinsäureanhydrid-Polyamin ist,
    wobei die Additivkombination, bezogen auf das Gewicht, mindestens ein Teil Bor auf jeweils 250 in dem aromatischen Amin-Antioxidans vorhandenen Teile Stickstoff enthält.
  2. Verwendung nach Anspruch 1, bei der das aromatische Amin-Antioxidans ausgewählt ist aus alkylsubstituiertem Phenylamin, alkylsubstituiertem Diphenylamin, alkylsubstituiertem Phenyl-α-naphthylamin und Mischungen derselben.
EP96305869A 1995-08-09 1996-08-09 Verwendung einer Schmiermittelzusammensetzung, enthaltend eine Mischung von Antioxidationsadditiven Expired - Lifetime EP0758016B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9516326.7A GB9516326D0 (en) 1995-08-09 1995-08-09 Lubricant composition containing antioxidant additive combination
GB9516326 1995-08-09

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EP0758016A1 EP0758016A1 (de) 1997-02-12
EP0758016B1 true EP0758016B1 (de) 2002-04-17

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Publication number Priority date Publication date Assignee Title
FR2762848B1 (fr) * 1997-05-05 2000-02-04 Chevron Res & Tech Utilisation de composes borates pour ameliorer la compatibilite d'huiles lubrifiantes avec des elastomeres fluorocarbones
HU226481B1 (en) * 2005-12-16 2009-03-02 Pannon Egyetem Mechanically stabilizied rubber- bitumen composition combined with additives and procedure for making the same

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4657686A (en) * 1980-06-12 1987-04-14 Union Oil Company Of California Lubricating compositions
DE3568577D1 (en) * 1984-10-12 1989-04-13 Ciba Geigy Ag Boron containing thioethers as additives
JP2617807B2 (ja) * 1990-03-16 1997-06-04 日本石油株式会社 エンジン油組成物
JP2859077B2 (ja) * 1993-04-09 1999-02-17 出光興産株式会社 潤滑油組成物
US5344579A (en) * 1993-08-20 1994-09-06 Ethyl Petroleum Additives, Inc. Friction modifier compositions and their use
JP3650629B2 (ja) * 1993-10-29 2005-05-25 東燃ゼネラル石油株式会社 潤滑油組成物
JPH07258671A (ja) * 1994-03-24 1995-10-09 Lubrizol Corp:The 無灰の低リン潤滑剤
AU706587B2 (en) * 1994-04-19 1999-06-17 Lubrizol Corporation, The Lubricating compositions with improved oxidation resistance containing a dispersant and an antioxidant

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DE69620689D1 (de) 2002-05-23
DE69620689T2 (de) 2002-10-17
EP0758016A1 (de) 1997-02-12
GB9516326D0 (en) 1995-10-11

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