EP2574656B1 - Schmierstoffzusammensetzung enthaltend p-Alkoxy-N,N-dialkyl-Anilin - Google Patents

Schmierstoffzusammensetzung enthaltend p-Alkoxy-N,N-dialkyl-Anilin Download PDF

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Publication number
EP2574656B1
EP2574656B1 EP11183113.7A EP11183113A EP2574656B1 EP 2574656 B1 EP2574656 B1 EP 2574656B1 EP 11183113 A EP11183113 A EP 11183113A EP 2574656 B1 EP2574656 B1 EP 2574656B1
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EP
European Patent Office
Prior art keywords
lubricating oil
mass
oil composition
tbn
compound
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EP11183113.7A
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English (en)
French (fr)
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EP2574656A1 (de
Inventor
Joseph Peter Hartley
Gabriele Candido
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Infineum International Ltd
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Infineum International Ltd
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Priority to EP11183113.7A priority Critical patent/EP2574656B1/de
Priority to US13/623,892 priority patent/US20130252865A1/en
Priority to CN201210369519.8A priority patent/CN103074143B/zh
Priority to JP2012214236A priority patent/JP5973301B2/ja
Priority to SG2012072153A priority patent/SG188776A1/en
Priority to CA2791282A priority patent/CA2791282C/en
Publication of EP2574656A1 publication Critical patent/EP2574656A1/de
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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
    • 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
    • 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
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
    • 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
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/36—Seal compatibility, e.g. with rubber
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/42—Phosphor free or low phosphor content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/43—Sulfur free or low sulfur content compositions
    • 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
    • C10N2030/40—Low content or no content compositions
    • C10N2030/45—Ash-less or low ash content
    • 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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion 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

Definitions

  • N, N-dialkylaniline and substituted derivatives such as N,N-dialkylethoxyaniline can be prepared by reacting the appropriate aniline or substituted derivatives such as ethoxyaniline with aldehydes/ketones in a 1:2 or excess molar ratio in the presence of a reducing agent such as sodium triacetoxyborohydride in dichloromethane solvent.
  • a reducing agent such as sodium triacetoxyborohydride in dichloromethane solvent.
  • Lubricating oil compositions of the present invention may further contain one or more ashless dispersants, which effectively reduce formation of deposits upon use in gasoline and diesel engines, when added to lubricating oils.
  • Ashless dispersants useful in the compositions of the present invention comprises an oil soluble polymeric long chain backbone having functional groups capable of associating with particles to be dispersed.
  • such dispersants comprise amine, alcohol, amide or ester polar moieties attached to the polymer backbone, often via a bridging group.
  • Preferred groups of dispersant include polyamine-derivatized poly ⁇ -olefin, dispersants, particularly ethylene/butene alpha-olefin and polyisobutylene-based dispersants.
  • Particularly preferred are ashless dispersants derived from polyisobutylene substituted with succinic anhydride groups and reacted with polyethylene amines, e.g. polyethylene diamine, tetraethylene pentamine; or a polyoxyalkylene polyamine, e.g. polyoxypropylene diamine, trimethylolaminomethane; a hydroxy compound, e.g. pentaerythritol; and combinations thereof.
  • tetraethylene pentamine and (C) a polyhydric alcohol or polyhydroxy-substituted aliphatic primary amine, e.g. pentaerythritol or trismethylolaminomethane, as described in U.S. Patent No. 3,632,511 .
  • Mannich base condensation products Another class of ashless dispersants comprises Mannich base condensation products. Generally, these products are prepared by condensing about one mole of an alkyl-substituted mono- or polyhydroxy benzene with about 1 to 2.5 moles of carbonyl compound(s) (e.g., formaldehyde and paraformaldehyde) and about 0.5 to 2 moles of polyalkylene polyamine, as disclosed, for example, in U.S. Patent No. 3,442,808 .
  • carbonyl compound(s) e.g., formaldehyde and paraformaldehyde
  • Such Mannich base condensation products may include a polymer product of a metallocene catalyzed polymerization as a substituent on the benzene group, or may be reacted with a compound containing such a polymer substituted on a succinic anhydride in a manner similar to that described in U.S. Patent No. 3,442,808 .
  • Examples of functionalized and/or derivatized olefin polymers synthesized using metallocene catalyst systems are described in the publications identified supra .
  • the dispersant can be further post treated by a variety of conventional post treatments such as boration, as generally taught in U.S. Patent Nos. 3,087,936 and 3,254,025 .
  • Boration of the dispersant is readily accomplished by treating an acyl nitrogen-containing dispersant with a boron compound such as boron oxide, boron halide boron acids, and esters of boron acids, in an amount sufficient to provide from about 0.1 to about 20 atomic proportions of boron for each mole of acylated nitrogen composition.
  • Useful dispersants contain from about 0.05 to about 2.0 mass %, e.g., from about 0.05 to about 0.7 mass % boron.
  • the zinc dihydrocarbyl dithiophosphate can therefore comprise zinc dialkyl dithiophosphates.
  • the present invention may be particularly useful when used with lubricant compositions containing phosphorus levels of from about 0.02 to about 0.12 mass %, such as from about 0.03 to about 0.10 mass %, or from about 0.05 to about 0.08 mass %, based on the total mass of the composition.
  • lubricating oil compositions of the present invention contain zinc dialkyl dithiophosphate derived predominantly (e.g., over 50 mol. %, such as over 60 mol. %) from secondary alcohols.
  • Oxidation inhibitors or antioxidants reduce the tendency of mineral oils to deteriorate in service. Oxidative deterioration can be evidenced by sludge in the lubricant, varnish-like deposits on the metal surfaces, and by viscosity growth.
  • Oxidative deterioration can be evidenced by sludge in the lubricant, varnish-like deposits on the metal surfaces, and by viscosity growth.
  • Such oxidation inhibitors include hindered phenols, alkaline earth metal salts of alkylphenolthioesters having preferably C 5 to C 12 alkyl side chains, calcium nonylphenol sulfide, oil soluble phenates and sulfurized phenates, phosphosulfurized or sulfurized hydrocarbons, phosphorous esters, metal thiocarbamates, oil soluble copper compounds as described in U.S. Patent No. 4,867,890 , and molybdenum-containing compounds.
  • Friction modifiers and fuel economy agents that are compatible with the other ingredients of the final oil may also be included.
  • examples of such materials include glyceryl monoesters of higher fatty acids, for example, glyceryl mono-oleate; esters of long chain polycarboxylic acids with diols, for example, the butane diol ester of a dimerized unsaturated fatty acid; oxazoline compounds; and alkoxylated alkyl-substituted mono-amines, diamines and alkyl ether amines, for example, ethoxylated tallow amine and ethoxylated tallow ether amine.
  • Pour point depressants otherwise known as lube oil flow improvers (LOFI)
  • LOFI lube oil flow improvers
  • Such additives are well known. Typical of those additives that improve the low temperature fluidity of the fluid are C 8 to C 18 dialkyl fumarate/vinyl acetate copolymers, and polymethacrylates.
  • Foam control can be provided by an antifoamant of the polysiloxane type, for example, silicone oil or polydimethyl siloxane.
  • Fully formulated lubricating oil compositions of the present invention preferably have a TBN of at least 8.5, preferably at least 9, such as from about 8.5 to about 13, preferably from about 9 to about 13, and more preferably from about 9 to about 11 mg KOH/g (ASTM D-2896 and/or ASTM D-4739).
  • fully formulated lubricating oil compositions of the present invention derive at least 5 %, preferably at least 10 %, more preferably at least 20 % of the compositional TBN from ashless TBN sources including at least one compound of formula (I). More preferably, fully formulated lubricating oil compositions of the present invention derive at least 5 %, preferably at least 10 %, more preferably at least 20 % of the compositional TBN from at least one compound of formula (I), and less than 25 %, preferably less than 20 %, more preferably less than 15 % of the compositional TBN from ashless TBN sources other than compounds of formula (I), including basic dispersants.
  • weight (and mass) percents expressed herein are based on active ingredient (A.I.) content of the additive, and/or additive-package, exclusive of any associated diluent.
  • active ingredient (A.I.) content of the additive, and/or additive-package exclusive of any associated diluent.
  • detergents are conventionally formed in diluent oil, which is not removed from the product, and the TBN of a detergent is conventionally provided for the active detergent in the associated diluent oil. Therefore, weight (and mass) percents, when referring to detergents are (unless otherwise indicated) total weight (or mass) percent of active ingredient and associated diluent oil.
  • a fully formulated lubricating oil composition containing dispersant, a detergent mixture, antioxidant, ZDDP antiwear agent, pour point depressant and viscosity modifier, in base oil was prepared.
  • This lubricating oil composition which was representative of a commercial crankcase lubricant, was used as a reference lubricant.
  • Fully formulated lubricating oil compositions containing 1.68 mass% of the compounds of Synthesis Example 1 (Oil A) and Synthesis Example 2 (Oil B) were prepared. Also tested were fully formulated lubricating oil compositions containing 1.00 mass % (Oil C) and 2.00 mass % (Oil D) of the comparative compound of Synthesis Example 3.
  • An additional amount of base oil was added to each of the samples to provide comparable total mass.
  • the compounds of the invention as used in Oil A and Oil B effectively increased the TBN of the lubricating oil composition as measured by ASTM D-4739, without contributing to SASH content.
  • the comparative compound of Synthesis Example 3 having a di-alkyl branching arrangement not according to the present invention gave no significant improvement in TBN. This was so even in the case of Oil D where a greater amount of compound was used (2.00 mass% vs. 1.64 mass%).
  • Oil A and a similar oil containing N,N-di-n-hexyl-4-ethoxyaniline in place of the compound of the invention were tested in the VW-6/AK6 test.
  • This procedure tests compatibility of lubricating oils with Viton fluoroelastomer seal materials.
  • the elongation at break for a reference oil containing neither compound was on average -34.5% compared to a new seal.
  • For Oil A the average was -51% and for the oil containing N,N-di-n-hexyl-4-ethoxyaniline, -64%.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (12)

  1. Schmierölzusammensetzung, die eine größere Menge an Öl mit Schmierviskosität und eine kleinere Menge einer oder mehrerer Verbindungen der Formel (I):
    Figure imgb0010
     umfasst, in der R1, R2, R3, R4 und R5 unabhängig Alkyl oder substituiertes Alkyl wiedergeben, die keinen Arylsubstituenten aufweisen.
  2. Schmierölzusammensetzung nach Anspruch 1, in der R1 Methyl oder Ethyl, vorzugsweise Methyl wiedergibt.
  3. Schmierölzusammensetzung nach Anspruch 1 oder Anspruch 2, in der R3 Methyl oder Ethyl wiedergibt, vorzugsweise Ethyl.
  4. Schmierölzusammensetzung nach einem der vorhergehenden Ansprüche, in der R5 Methyl oder Ethyl wiedergibt, vorzugsweise Ethyl.
  5. Schmierölzusammensetzung nach einem der vorhergehenden Ansprüche, die eine Gesamtbasenzahl (TBN) von mindestens 6 mg KOH/g, vorzugsweise 6 bis 15 mg KOH/g aufweist, gemessen mittels ASTM D-4739.
  6. Schmierölzusammensetzung gemäß einem der vorhergehenden Ansprüche, die einen Sulfataschegehalt von nicht größer als 1,1, vorzugsweise nicht größer als 1,0, insbesondere nicht größer als 0,8 Masse% aufweist.
  7. Schmierölzusammensetzung nach einem der vorhergehenden Ansprüche, in der mindestens 10%, vorzugsweise mindestens 15%, insbesondere mindestens 20% der TBN der Zusammensetzung, wie mittels ASTM D-4379 gemessen, aus aschefreien Quellen von TBN abgeleitet sind, einschließlich der mindestens einen Verbindung der Formel (1).
  8. Schmierölzusammensetzung gemäß einem der vorhergehenden Ansprüche, die einen Schwefelgehalt von weniger als 0,4 Masse% aufweist und nicht mehr als 1200 ppm Phosphor.
  9. Konzentrat zur Herstellung einer Schmierölzusammensetzung gemäß einem der vorhergehenden Ansprüche, wobei das Konzentrat 2,5 bis 30 Masse% einer oder mehrerer Verbindungen der Formel I wie in Anspruch 1 definiert, 10 bis 20 Masse% Stickstoff enthaltendes Dispergiermittel, 2 bis 20 Masse% aminisches Antioxidans, phenolisches Antioxidans, Molybdänverbindung oder eine Mischung davon, 5 bis 40 Masse% Detergens und von 2 bis 20 Masse% Metalldikohlenwasserstoffdithiophosphat aufweist.
  10. Verbindung der Formel (I):
    Figure imgb0011
     in der R1, R2, R3, R4 und R5 unabhängig Alkyl oder substituiertes Alkyl wiedergeben, die keinen Arylsubstituenten aufweisen.
  11. Verfahren zum Erhöhen der TBN einer Schmierölzusammensetzung ohne gleichzeitige Erhöhung des Sulfataschegehalts, bei welchem Verfahren der Schmierölzusammensetzung eine oder mehrere Verbindungen gemäß Anspruch 10 hinzugesetzt werden.
  12. Verwendung einer Verbindung gemäß Anspruch 10 als aschefreie TBN-Quelle für eine Schmierölzusamensetzung.
EP11183113.7A 2011-09-28 2011-09-28 Schmierstoffzusammensetzung enthaltend p-Alkoxy-N,N-dialkyl-Anilin Active EP2574656B1 (de)

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Application Number Priority Date Filing Date Title
EP11183113.7A EP2574656B1 (de) 2011-09-28 2011-09-28 Schmierstoffzusammensetzung enthaltend p-Alkoxy-N,N-dialkyl-Anilin
US13/623,892 US20130252865A1 (en) 2011-09-28 2012-09-21 Lubricating oil compositions
CN201210369519.8A CN103074143B (zh) 2011-09-28 2012-09-27 润滑油组合物
JP2012214236A JP5973301B2 (ja) 2011-09-28 2012-09-27 潤滑油組成物
SG2012072153A SG188776A1 (en) 2011-09-28 2012-09-27 Lubricating oil compositions
CA2791282A CA2791282C (en) 2011-09-28 2012-09-28 Lubricating oil compositions

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EP2574656B1 true EP2574656B1 (de) 2014-04-02

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CA (1) CA2791282C (de)
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JP2013072088A (ja) 2013-04-22
CN103074143A (zh) 2013-05-01
EP2574656A1 (de) 2013-04-03
US20130252865A1 (en) 2013-09-26
CA2791282A1 (en) 2013-03-28
SG188776A1 (en) 2013-04-30
CA2791282C (en) 2019-05-14
CN103074143B (zh) 2017-03-01
JP5973301B2 (ja) 2016-08-23

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