US20100269774A1 - Lubricating composition for use in diesel engines compatible with biofuel - Google Patents

Lubricating composition for use in diesel engines compatible with biofuel Download PDF

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Publication number
US20100269774A1
US20100269774A1 US12/669,807 US66980708A US2010269774A1 US 20100269774 A1 US20100269774 A1 US 20100269774A1 US 66980708 A US66980708 A US 66980708A US 2010269774 A1 US2010269774 A1 US 2010269774A1
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Prior art keywords
oxidant
lubricating composition
mass
biofuel
amine
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Abandoned
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US12/669,807
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English (en)
Inventor
Noriaki Shinoda
Eiji Nagatomi
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Shell USA Inc
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Individual
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Assigned to SHELL OIL COMPANY reassignment SHELL OIL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SHINODA, NORIAKI, NAGATOMI, EIJI
Publication of US20100269774A1 publication Critical patent/US20100269774A1/en
Abandoned legal-status Critical Current

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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
    • 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
    • C10M141/06—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 nitrogen-containing compound
    • 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
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • 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
    • 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
    • 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
    • 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
    • C10M2203/102—Aliphatic fractions
    • C10M2203/1025—Aliphatic fractions used as base material
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C10M2215/065—Phenyl-Naphthyl amines
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/067—Polyaryl amine alkanes
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • 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
    • C10N2020/081—Biodegradable 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
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • 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
    • C10N2030/78—Fuel contamination
    • 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
    • C10N2040/252—Diesel engines
    • 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
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines

Definitions

  • This invention relates to lubricating compositions for use in diesel engines that use biofuels.
  • Biofuels for use in the diesel engines used in automotive vehicles have in some cases been produced by methyl esterification of plant oils, taking mainly rapeseed oil or sunflower oil as their raw material in France, German, and Italy within the EU, and mainly soybean oil as their raw material in the United States. In many cases, these fuels are used by mixing about 20% in a light oil.
  • biodiesel fuels There are several points about these biodiesel fuels which must be borne in mind when using them. They have aspects which demand improvement simply in fuel terms in that their viscosities and pour points are rather high, and they are prone to oxidise because, being derived from plant oils, they contain many unsaturated fatty acids. Furthermore, these biodiesel fuels may compete directly with edible vegetable oils, and so they have not been studied as much as the above-mentioned alcohol fuels as alternatives to gasoline, and there have hardly been any attempts to improve lubricating oils in association with biodiesel fuels.
  • the inventors have discovered that it is possible to inhibit ageing, and in particular degradation of the detergent performance of the lubricating oil, even after admixture with biodiesel fuel, by combining different types of anti-oxidant, a phenolic anti-oxidant and an amine-based anti-oxidant, in the lubricating oil composition.
  • the present invention provides a lubricating composition for use in diesel engines compatible with biofuel, the lubricating composition comprising a base oil belonging to Group III and/or Group II of the API base oil categories, from 0.5 to 5% by mass of a phenolic anti-oxidant and from 0.5 to 5% by mass of an amine-based anti-oxidant, the total content of the anti-oxidants being at least 2% by mass.
  • this invention it is possible to inhibit rapid degradation of the detergent performance and accelerated ageing of the lubricating oil, even after admixture of biodiesel fuel in the lubricating oil, by using different types of anti-oxidant, a phenolic anti-oxidant and an amine-based anti-oxidant, together, and thus it is possible to use the lubricating oil stably over a long period.
  • biodiesel oils differ substantially from light oils is the content of constituent oxygen atoms. Also, it is believed that, since they contain double bonds derived from unsaturated fatty acids, the combustion reaction itself differs.
  • the flash point is higher than in light oils and they are more prone to evaporate.
  • the reaction may cease in the elementary process on the way to complete combustion, and the unreacted portion will often mix with the lubricating oil or the unburnt constituents themselves will be mixed with the lubricating oil, causing the formation of sludge in the lubricating oil and accelerating ageing of the lubricating oil through oxidation.
  • the lubricating oils will be characterised by being used under more rigorous conditions even than when exposed to high temperatures when using only light oils as the fuel.
  • base oils of this invention it is possible to use any suitable mineral oil or synthetic oil, and normally it is possible to use base oils, singly or in mixtures, that belong to Group III and Group II of the base oil categories of the API (American Petroleum Institute).
  • Group III and Group II base oils include, for example, paraffinic mineral oils obtained by a high degree of hydrorefining in respect of lubricating oil fractions obtained by atmospheric distillation of crude oil, base oils refined by the Isodewax process which dewaxes and substitutes the wax produced by the dewaxing process with isoparaffins, base oils refined by the Mobil wax isomerisation process, and the so-called GTL (gas-to-liquid) base oils solvent dewaxed or catalyst dewaxed after synthesis by the Fischer-Tropsch method.
  • GTL gas-to-liquid base oils solvent dewaxed or catalyst dewaxed after synthesis by the Fischer-Tropsch method.
  • synthetic oils include also those that may be designated as “synthetic oils” according to the rulings of the NAD (National Advertising Division) which is responsible for advertising adjudications in America.
  • Phenolic anti-oxidants and amine-based anti-oxidants are blended together in these base oils.
  • phenolic anti-oxidants mention may be made of 2,6-di-t-butylphenol, 2,6-di-t-butyl-p-cresol, 2,6-di-t-butyl-4-ethylphenol, 2,2′-methylenebis(4-methyl-6-t-butylphenol), 2,2′-methylenebis(4-ethyl-6-t-butylphenol), 4,4′-bis(2,6-di-t-butylphenol), 4,4′-thiobis(6-t-butyl-o-cresol), and alkyl alcohol esters of 3-(4-hydroxy-3,5-di-t-butyl-phenyl)propionic acid such as 6 methylheptyl alcohol esters of 3-(4-hydroxy-3,5-di-t-butyl-phenyl)propionic acid.
  • amine-based anti-oxidants mention may be made of diphenylamines, p,p′-dioctyldiphenylamines, p,p′-dinonyldiphenylamines, p,p′-didodecyldiphenylamines, phenyl- ⁇ -naphthylamines, p-octylphenyl- ⁇ -naphthylamines, p-nonylphenyl- ⁇ -naphthylamines and p-dodecylphenyl- ⁇ -naphthylamines, and mixtures thereof.
  • diphenylamines are a diphenylamine which is the reaction product of N-phenylbenzeneamine and 2,4,4-trimethylpentene.
  • the amount of the above-mentioned phenolic anti-oxidant is from 0.5 to 5.0% by mass based on the total amount of the lubricating oil composition, and preferably from 0.5 to 2% by mass.
  • the amount of the above-mentioned amine-based anti-oxidant is from 0.5 to 5.0% by mass based on the total amount of the lubricating oil composition, and preferably from 0.5 to 2% by mass.
  • the phenolic anti-oxidants and the amine-based anti-oxidants are used respectively in the above-mentioned amounts, but it is further required that the total amount of the two anti-oxidants at the same time is not less than 2% by mass. If the total amount of both is less than that, the expected effect will not be obtained.
  • the present invention provides a method of operating a diesel engine comprising lubricating the diesel engine with a lubricating composition according to the present invention and using a biofuel, preferably derived from rapeseed oil, as fuel.
  • the biodiesel fuel (BDF) was a methyl ester derived from rapeseed oil and was prepared so as to have the properties shown in Table 2.
  • Base oil a mineral oil belonging to API Group III
  • Phenolic anti-oxidant 6 methylheptyl alcohol ester of 3-(4-hydroxy-3,5-di-t-butyl-phenyl)propionic acid
  • Amine-based anti-oxidant diphenylamine being a reaction product of N-phenylbenzeneamine and 2,4,4-trimethylpentene
  • Additives package additives containing dispersant, ZnDTP and detergent.
  • Comparative Example 6 was a composition with a JASO (Engine Oil Standards Implementation Panel) DH-2 level diesel combustion engine oil for use in automotive vehicles.
  • JASO Engine Oil Standards Implementation Panel
  • Evaluation of the hot tube tests was from 0 to 10 in fractions of 0.5, and 7 and above was set as the pass mark.
  • Example 1 Example 2
  • Example 3 Example 4
  • Base oil 86 85 85.5
  • 1.0 4.0 antioxidant Additives package 12 12 12
  • Total 100 100
  • Comparative Example 2 used 2.5% by mass of only the amine-based anti-oxidant, and although the total amount exceeded 2% by mass the hot tube score was poor at 2.0. More amine-based anti-oxidant was added to Comparative Example 3 than in Comparative Example 2, but the hot tube score rose only to 5.0.
  • Comparative Example 4 used 2.5% by mass of only the phenolic anti-oxidant, and although the total amount exceeded 2% by mass the hot tube score was poor at 3.0.
  • Comparative Example 5 used both anti-oxidants together, but the total amount was less than 2% by mass and so the hot-tube score was poor at 2.5. A satisfactory effect was thus not obtained for any of Comparative Examples 1-5
  • Comparative Example 6 had no admixture of biofuel, and even though no phenolic anti-oxidant or amine-based anti-oxidant was used, the hot tube score was 7.0 and it can be seen that a satisfactory effect was obtained.
US12/669,807 2007-07-23 2008-07-21 Lubricating composition for use in diesel engines compatible with biofuel Abandoned US20100269774A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2007-190658 2007-07-23
JP2007190658A JP2009024123A (ja) 2007-07-23 2007-07-23 バイオ燃料対応ディーゼルエンジン用潤滑油組成物。
PCT/EP2008/059543 WO2009013275A1 (en) 2007-07-23 2008-07-21 Lubricating composition for use in diesel engines compatible with biofuel

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US13/448,054 Abandoned US20130102509A1 (en) 2007-07-23 2012-04-16 Lubricating composition for use in diesel engines compatible with biofuel

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US (2) US20100269774A1 (ja)
EP (1) EP2179011B1 (ja)
JP (1) JP2009024123A (ja)
CN (1) CN101796171B (ja)
AR (1) AR068609A1 (ja)
BR (1) BRPI0814579B1 (ja)
RU (1) RU2456333C2 (ja)
WO (1) WO2009013275A1 (ja)

Cited By (3)

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WO2014078083A1 (en) 2012-11-19 2014-05-22 The Lubrizol Corporation Coupled phenols for use in biodiesel engines
WO2018125567A1 (en) 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition with alkylated naphthylamine
WO2018125569A1 (en) 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition including n-alkylated dianiline

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US7960322B2 (en) * 2007-10-26 2011-06-14 Chevron Oronite Company Llc Lubricating oil compositions comprising a biodiesel fuel and an antioxidant
CA2766063A1 (en) 2009-06-26 2010-12-29 The Lubrizol Corporation Engine oil formulations for biodiesel fuels
BR112012002608A2 (pt) * 2009-08-05 2016-03-29 Basf Se composição lubrificante, e, método para melhorar o desempenho de uma composição lubrificante.
JP2017039841A (ja) * 2015-08-19 2017-02-23 コスモ石油ルブリカンツ株式会社 内燃機関用潤滑油組成物
WO2018156304A1 (en) 2017-02-21 2018-08-30 Exxonmobil Research And Engineering Company Lubricating oil compositions and methods of use thereof

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WO2014078083A1 (en) 2012-11-19 2014-05-22 The Lubrizol Corporation Coupled phenols for use in biodiesel engines
US10113132B2 (en) 2012-11-19 2018-10-30 The Lubrizol Corporation Coupled phenols for use in biodiesel engines
WO2018125567A1 (en) 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition with alkylated naphthylamine
WO2018125569A1 (en) 2016-12-27 2018-07-05 The Lubrizol Corporation Lubricating composition including n-alkylated dianiline
US11162048B2 (en) 2016-12-27 2021-11-02 The Lubrizol Corporation Lubricating composition with alkylated naphthylamine

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AR068609A1 (es) 2009-11-25
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EP2179011A1 (en) 2010-04-28
EP2179011B1 (en) 2018-06-27
US20130102509A1 (en) 2013-04-25
BRPI0814579B1 (pt) 2018-03-27
CN101796171A (zh) 2010-08-04
CN101796171B (zh) 2014-12-17
RU2010106057A (ru) 2011-08-27
RU2456333C2 (ru) 2012-07-20
WO2009013275A1 (en) 2009-01-29
WO2009013275A9 (en) 2009-03-12

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