EP0758016A1 - Schmiermittelzusammensetzung, enthaltend eine Mischung von Antioxidationsadditiven - Google Patents

Schmiermittelzusammensetzung, enthaltend eine Mischung von Antioxidationsadditiven Download PDF

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Publication number
EP0758016A1
EP0758016A1 EP96305869A EP96305869A EP0758016A1 EP 0758016 A1 EP0758016 A1 EP 0758016A1 EP 96305869 A EP96305869 A EP 96305869A EP 96305869 A EP96305869 A EP 96305869A EP 0758016 A1 EP0758016 A1 EP 0758016A1
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EP
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Prior art keywords
boron
additive combination
aromatic amine
antioxidant
lubricant composition
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EP96305869A
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English (en)
French (fr)
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EP0758016B1 (de
Inventor
David Gary Lawton Esso Petroleum Co. Ltd. Holt
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ExxonMobil Technology and Engineering Co
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Exxon 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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    • 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
    • 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
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    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • 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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    • 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-dithioatederived alcohol borates as antioxidant and antiwear additive for lubricants and fuels.
  • the present invention provides an additive combination comprising:
  • the weight ratio of boron to nitrogen contained in the aromatic amine antioxidant is from 1:1 to 1:250, more preferably from 1:10 to 1:200, most preferably from 1:20 to 1:100, and especially from 1:40 to 1:80.
  • Boron content is measured according to Inductively Coupled Plasma Emission Spectroscopy (ASTM D 5185). Nitrogen content is measured according to the Kjeldahl method (ASTM D 3228).
  • the present invention provides the use of boron or a boron-containing compound to enhance the antioxidant performance of an aromatic amine antioxidant in a lubricant composition.
  • aromatic amine antioxidant may be any aromatic amine compound suitable for use as an antioxidant in lubricant compositions.
  • aromatic amine is meant an amine compound wherein at least one nitrogen atom is bonded directly to at least one aryl moiety.
  • the amine compound is of the formula: where R 1 is a phenyl, C 7 -C 18 alkylphenyl, C 7 -C 18 alkoxyphenyl or naphthyl group;
  • both R 1 and R 2 are aryl groups; that is they are preferably each selected from the list of groups suitable for R 1 , as specified above.
  • R 3 is hydrogen.
  • the aromatic antioxidant is a diarylamine compound.
  • aromatic antioxidants examples include phenylamine, diphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-[4-1,3-dimethylbutylphenyl]-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, diphenylamine, N-phenyl-1-naphthylamine, N-phenyl-2-naphthylamine, di-[4-1,3-dimethylbutylphenyl]-amine, di-[4-(1,1,3,3-tetramethyl butyl)-phenyl]-amine, N-allyldiphenylamine, 4-isopropoxydiphenyl-amine and di-4-
  • the boron is preferably present in the lubricant composition according to the invention in the form of a borated compound, especially a borated dispersant.
  • the dispersant may be any suitable ashless or metal-containing compound suitable as a lubricant dispersant that is capable of being borated. Preferably however it is an ashless alkenyl-succinic acid or anhydride, or alkenyl-succinimide dispersant.
  • PIBSA polyisobutene-succinic acid or anhydride
  • PBSA-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 polymer is prepared via Ziegler/Natta polymerization using a bridged zirconecene and methyalumoxane co-catalyst.
  • Polymeric olefin may be converted to a 2-chloro-4-methylphenyl (cmp) ester via the Koch reaction (BF3- catalyzed carbonylation in a continuous reactor).
  • the ester may be aminated with polyamine.
  • Ethylene butene and other copolymer dispersants are described, for example, in International patent publication number WO95/29976, the disclosure of which is incorporated herein by reference.
  • borated dispersants include borated viscosity index improvers, borated detergents, alkyl borates and esters of borate 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 95.5 wt.%, more preferably from 80 to 98 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 boron-containing compound for example a borated dispersant, 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 polyaryloxy-siloxane 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)
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

Publications (2)

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

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EP (1) EP0758016B1 (de)
DE (1) DE69620689T2 (de)
GB (1) GB9516326D0 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2762848A1 (fr) * 1997-05-05 1998-11-06 Chevron Res & Tech Utilisation de composes borates pour ameliorer la compatibilite d'huiles lubrifiantes avec des elastomeres fluorocarbones
WO2007068990A1 (en) * 2005-12-16 2007-06-21 Pannon Egyetem Chemically stabilized asphalt rubber compositions and a mechanochemical method for preparing the same

Citations (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
US4689162A (en) * 1984-10-12 1987-08-25 Ciba-Geigy Corporation Boron-containing compounds
EP0447916A1 (de) * 1990-03-16 1991-09-25 Nippon Oil Co., Ltd. Motorölzusammensetzung
US5344579A (en) * 1993-08-20 1994-09-06 Ethyl Petroleum Additives, Inc. Friction modifier compositions and their use
EP0620267A1 (de) * 1993-04-09 1994-10-19 Idemitsu Kosan Company Limited Schmierölzusammensetzung
JPH07126681A (ja) * 1993-10-29 1995-05-16 Tonen Corp 潤滑油組成物
EP0673991A1 (de) * 1994-03-24 1995-09-27 The Lubrizol Corporation Aschefreies Schmiermittel
EP0678569A2 (de) * 1994-04-19 1995-10-25 The Lubrizol Corporation Schmiermittelzusammensetzungen mit hoher Oxidationsbeständigkeit die ein Dispergiermittel und ein Antioxidant enthalten

Patent Citations (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
US4689162A (en) * 1984-10-12 1987-08-25 Ciba-Geigy Corporation Boron-containing compounds
EP0447916A1 (de) * 1990-03-16 1991-09-25 Nippon Oil Co., Ltd. Motorölzusammensetzung
EP0620267A1 (de) * 1993-04-09 1994-10-19 Idemitsu Kosan Company Limited Schmierölzusammensetzung
US5344579A (en) * 1993-08-20 1994-09-06 Ethyl Petroleum Additives, Inc. Friction modifier compositions and their use
JPH07126681A (ja) * 1993-10-29 1995-05-16 Tonen Corp 潤滑油組成物
EP0673991A1 (de) * 1994-03-24 1995-09-27 The Lubrizol Corporation Aschefreies Schmiermittel
EP0678569A2 (de) * 1994-04-19 1995-10-25 The Lubrizol Corporation Schmiermittelzusammensetzungen mit hoher Oxidationsbeständigkeit die ein Dispergiermittel und ein Antioxidant enthalten

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* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 95, no. 005 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2762848A1 (fr) * 1997-05-05 1998-11-06 Chevron Res & Tech Utilisation de composes borates pour ameliorer la compatibilite d'huiles lubrifiantes avec des elastomeres fluorocarbones
EP0877073A1 (de) * 1997-05-05 1998-11-11 Chevron Chemical S.A. Die Verwendung von Borverbindungen zur Verbesserung der Kompatibilität von Schmierölen mit Fluoroelastomeren
US6124247A (en) * 1997-05-05 2000-09-26 Chevron Chemical S.A. Use of borated compounds for the improvement of the compatibility of lubricating oils with fluorocarbon elastomers
WO2007068990A1 (en) * 2005-12-16 2007-06-21 Pannon Egyetem Chemically stabilized asphalt rubber compositions and a mechanochemical method for preparing the same

Also Published As

Publication number Publication date
EP0758016B1 (de) 2002-04-17
GB9516326D0 (en) 1995-10-11
DE69620689D1 (de) 2002-05-23
DE69620689T2 (de) 2002-10-17

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