EP0678569B1 - Schmiermittelzusammensetzungen mit hoher Oxidationsbeständigkeit die ein Dispergiermittel und ein Antioxidant enthalten - Google Patents

Schmiermittelzusammensetzungen mit hoher Oxidationsbeständigkeit die ein Dispergiermittel und ein Antioxidant enthalten Download PDF

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Publication number
EP0678569B1
EP0678569B1 EP95302545A EP95302545A EP0678569B1 EP 0678569 B1 EP0678569 B1 EP 0678569B1 EP 95302545 A EP95302545 A EP 95302545A EP 95302545 A EP95302545 A EP 95302545A EP 0678569 B1 EP0678569 B1 EP 0678569B1
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Prior art keywords
acid
phosphorus
sulfur
carbon atoms
acids
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Revoked
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EP95302545A
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English (en)
French (fr)
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EP0678569A3 (de
EP0678569A2 (de
Inventor
Eric R. Schnur
Robert C. Richardson
James J. Schwind
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Lubrizol Corp
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Lubrizol Corp
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Application filed by Lubrizol Corp filed Critical Lubrizol Corp
Publication of EP0678569A2 publication Critical patent/EP0678569A2/de
Publication of EP0678569A3 publication Critical patent/EP0678569A3/de
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    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/063—Complexes of boron halides
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/065—Organic compounds derived from inorganic acids or metal salts derived from Ti or Zr
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/066—Organic compounds derived from inorganic acids or metal salts derived from Mo or W
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • 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
    • C10N2040/02—Bearings

Definitions

  • mononuclear Ar moieties include benzene moieties, such as 1,2,4-benzenetriyl; 1,2,3-benezenetriyl; 3-methyl-1,2,4-benzenetriyl; 2-methyl-5-ethyl-1,3,4-benzenetriyl; 3-propoxy-1,2,4,5-benzenetetrayl; 3-chloro-1,2,4-benzenetriyl; 1,2,3,5-benzenetetrayl; 3-cyclohexyl-1,2,4-benzenetriyl; and 3-azocyclopentyl-1,2,5-benzenetriyl, and pyridine moieties, such as 3,4,5-azabenzene; and 6-methyl-3,4,5-azabenzene.
  • benzene moieties such as 1,2,4-benzenetriyl; 1,2,3-benezenetriyl; 3-methyl-1,2,4-benzenetriyl; 2-methyl-5-ethyl-1,3,4-benzenetri
  • Ar is a benzene nucleus, lower alkylene bridged benzene nucleus, or a naphthalene nucleus.
  • Adol 60® (about 75% by weight of a straight chain C 22 primary alcohol, about 15% of a C 20 primary alcohol and about 8% of C 18 and C 24 alcohols) and Adol 320® (oleyl alcohol).
  • Adol® alcohols are marketed by Ashland Chemical.
  • the antioxidant (A) is at least one phenol antioxidant.
  • the phenol antioxidants include metal free hindered phenols. Alkylene coupled derivatives of hindered phenols and phenol sulfides or sulfur coupled phenols may also be used. Hindered phenols are defined as those containing a sterically hindered hydroxyl group, and these include those derivatives of dihydroxy aryl compounds wherein the hydroxyl groups are in the o- or p-position to each other.
  • phenolic materials include: 2-t-butyl-4-heptylphenol; 2-t-butyl-4-octylphenol; 2-t-butyl-4-dodecylphenol; 2,6-di-t-butyl-4-butylphenol; 2,6-di-t-butyl-4-heptylphenol; 2,6-di-t-butyl-4-dodecylphenol; 2,6-di-t-butyl-tetrapropenylphenol; 2-methyl-6-di-t-butyl-4-heptylphenol; 2,6-di-t-butyl-tripropenylphenol; 2,4-dimethyl-6-t-butylphenol; 2,6-t-butyl-4-ethylphenol; 4-t-butyl catechol; 2,4-di-t-butyl-p-cresol; 2,6-di-t-butyl-4-methylphenol; and 2-methyl-6-di-t-t-
  • the hydrocarbyl group is derived from a polyalkene.
  • the polyalkene includes homopolymers and interpolymers of polymerizable olefin monomers having from 2 up to 16, or from 2 up to 6, or from 2 to 4 carbon atoms.
  • the olefins may be monoolefins, such as ethylene, propylene, 1-butene, isobutene, and 1-octene, or polyolefinic monomers, including diolefinic monomers, such 1,3-butadiene and isoprene.
  • the interpolymer is a homopolymer.
  • heterocyclic amines examples include N-(hydroxyl lower alkyl)-morpholines, -thiomorpholines, -piperidines, -oxazolidines, -thiazolidines and the like.
  • each R' 1 is independently a methyl, ethyl, propyl, butyl, pentyl or hexyl group.
  • alkanolamines include mono-, di-, and triethanolamine, diethylethanolamine, ethylethanolamine, butyldiethanolamine, etc.
  • the polyamine is a fatty diamine.
  • the fatty diamines include mono- or dialkyl, symmetrical or asymmetrical ethylenediamines, propanediamines (1,2, or 1,3), and polyamine analogs of the above.
  • Suitable commercial fatty polyamines are Duomeen C® (N-coco-l 3-diaminopropane), Duomeen S® (N-soya-1,3-diaminopropane), Duomeen T® (N-tallow-1,3-diaminopropane), and Duomeen O® (N-oleyl-1,3-diaminopropane).
  • Duomeens® are commercially available from Armak Chemical Co., Chicago, Illinois.
  • alkylenepolyamines include methylenepolyamines, ethylenepolyamines, butylenepolyamines, propylenepolyamines, pentylenepolyamines, etc.
  • the higher homologs and related heterocyclic amines, such as piperazines and N-amino alkyl-substituted piperazines, are also included.
  • Specific examples of such polyamines are ethylenediamine, triethylenetetramine, tris-(2-aminoethyl)amine, propylenediamine, trimethylenediamine, tripropylenetetramine, triethylenetetraamine, tetraethylenepentamine, hexaethyleneheptamine, pentaethylenehexamine, etc.
  • Higher homologs obtained by condensing two or more of the above-noted alkyleneamines are similarly useful as are mixtures of two or more of the aforedescribed polyamines.
  • the polyamine is an ethylenepolyamine.
  • ethylenepolyamine Such polyamines are described in detail under the heading Ethylene Amines in Kirk Othmer's "Encyclopedia of Chemical Technology", 2d Edition, Vol. 7, pages 22-37, Interscience Publishers, New York (1965).
  • Ethylenepolyamines are often a complex mixture of polyalkylenepolyamines including cyclic condensation products.
  • Other useful types of polyamine mixtures are those resulting from stripping of the above-described polyamine mixtures to leave, as residue, what is often termed "polyamine bottoms".
  • alkylenepolyamine bottoms can be characterized as having less than 2%, usually less than 1% (by weight) material boiling below 200°C.
  • the boron compounds include mono-, di-, and tri-organic esters of boric acid and alcohols or phenols.
  • the alcohols include methanol, ethanol, propanol, butanol, 1-octanol, benzyl alcohol, ethylene glycol, glycerol, and Cellosolve.
  • Methods for preparing the esters are known and disclosed in the art (such as "Chemical Reviews," pp. 959-1064, Vol. 56).
  • the R 28 group is a hydrocarbyl group that is directly bonded to the aromatic group Ar.
  • R 28 typically contains from 6 to 80, or from 7 to 30, or from 8 to 25, or from 8 to 15 carbon atoms.
  • R 28 groups include butyl, isobutyl, pentyl, octyl, nonyl, dodecyl, 5-chlorohexyl, 4-ethoxypentyl, 3-cyclohexyloctyl, 2,3,5-trimethylheptyl, propylene tetramer, triisobutenyl and substituents derived from one of the above described olefins or polyalkenes.
  • Dodecylbenzene "bottoms" sulfonic acids are the material leftover after the removal of dodecylbenzene sulfonic acids that are used for household detergents.
  • the "bottoms” may be straight-chain or branched-chain alkylates with a straight-chain dialkylate preferred.
  • SO 3 a detergent manufactured by-products by reaction with, e.g., SO 3 . See, for example, the article “Sulfonates” in Kirk-Othmer “Encyclopedia of Chemical Technology", Second Edition, Vol. 19, pp. 291 et seq. published by John Wiley & Sons, N.Y. (1969).
  • the pressure Prior to reaching the peak reaction temperature, the pressure starts to decrease and continues to decrease steadily as the gaseous reactants are consumed. After about 10 hours at a reaction temperature of about 182°C, the pressure is 2.14-2.34 MPa (310-340 psig) and the rate of pressure change is about 35-69 kPa (5-10 psig) per hour.
  • the unreacted hydrogen sulfide and isobutene are vented to a recovery system. After the pressure in the reactor has decreased to atmospheric, the sulfurized mixture is recovered as a liquid.
  • Examples of phosphorus or boron containing antiwear/extreme pressure agents (C)(ii) include a phosphoric acid ester or salt thereof; a phosphite; a phosphorus-containing carboxylic ester, ether, or amide; a borated dispersant; an alkali metal or a mixed alkali metal, alkaline earth metal borate; a borated overbased metal salt; and a borate ester.
  • the phosphorus acids include the phosphoric, phosphonic, phosphinic and thiophosphoric acids including dithiophosphoric acid as well as the monothiophosphoric acid, thiophosphinic and thiophosphonic acids.
  • (C)(ii) is a phosphorus acid ester is prepared by reacting one or more phosphorus acid or anhydride with an alcohol containing from 1 up to 30, or from 2 up to 24, or from 3 up to 12 carbon atoms.
  • the phosphorus acids or anhydrides and the alcohols are described above.
  • useful phosphorus acid esters include the phosphoric acid di- and tri- esters prepared by reacting a phosphoric acid or anhydride with cresol alcohols.
  • An example is tricresylphosphate.
  • a 75W-90 lubricant is prepared by incorporating 3.5 % of dinonyldiphenylamine, 1.2% of the product of Example B-4, 0.03% of a substituted imidiazoline from oleylamine, 0.1% oleylamide, 1.7% of the product of Example P-3, 4.6% of the product of Example S-1, 0.1% of a reaction product of C 9 mercaptan and dimercaptodithiodiazole, 0.1 % of a reaction product of heptylphenol, formaldehyde and dimercaptothiadiazole, 0.03% of TOLAD 370® available from Petrolite Chemical, 0.1 % of a copolymer of methylacrylate and 2-ethylhexylacrylate, 0.5 % by weight of a maleic anhydride-styrene copolymer esterified with C 8-18 and C 4 alcohols and post-treated with aminopropylmorpholine, 30 ppm of Dow Corning 200® fluid, 2.01

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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)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)

Claims (9)

  1. Schmierzusammensetzung, umfassend eine Hauptmenge eines Öls mit Schmierviskosität mit einer lodzahl von weniger als 4, (A) ein oder mehrere aschefreie Antioxidationsmittel, ausgewählt aus Amin-Antioxidationsmitteln, Dithiophosphorsäureestern, Phenol-Antioxidationsmitteln, Dithiocarbamaten und aromatischen Phosphiten, (B) 0,01 Gew.-% bis 3 Gew.-% mindestens eines borhaltigen Dispergiermittels oder Detergenz und gegebenenfalls (C) mindestens ein Additiv, ausgewählt aus (i) einem schwefelhaltigen Antiverschleiß- oder Hochdruckmittel, (ii) einem phosphor- oder borhaltigen Antiverschleiß- oder Hochdruckmittel und (iii) Gemischen davon, mit der Maßgabe, dass (C) verschieden von (A) ist, und wobei die Gesamtmenge an Antioxidanzien 2 bis 10 Gew.-% beträgt.
  2. Zusammensetzung nach Anspruch 1, wobei das Antioxidationsmittel (A) ausgewählt ist aus aromatischen substituierten Aminen, gehinderten Phenolen, schwefelgekoppelten Phenolen, aromatischen Phosphiten, alkylengekoppelten Dithiocarbamaten und Dithiocarbamatestern, die das Umsetzungsprodukt einer Dithiocarbaminsäure oder eines Salzes mit einem/einer oder mehreren ungesättigten Amiden, Carbonsäuren, -anhydriden oder -estern und Ethern sind.
  3. Zusammensetzung nach Anspruch 1, wobei das Antioxidationsmittel (A) ausgewählt ist aus einem Diphenylamin, einem alkylengekoppelten Dithiocarbamat und einem Dithiocarbamatester, hergestellt durch Umsetzen einer Dithiocarbaminsäure oder eines Salzes mit einem Acrylat oder Methacrylat.
  4. Zusammensetzung nach einem der vorstehenden Ansprüche, wobei (B) mindestens ein Dispergiermittel, ausgewählt aus borierten, acylierten Aminen, Carbonsäureestern, Mannich-Reaktionsprodukten und Hydrocarbyl-substituierten Aminen, oder mindestens ein Detergenz ist, das ein boriertes, überbasifiziertes Metallsalz ist.
  5. Zusammensetzung nach einem der Ansprüche 1 bis 3, wobei (B) mindestens ein Dispergiermittel, das ein boriertes Reaktionsprodukt eines Hydrocarbyl-substituiertenen carboxylhaltigen Acylierungsmittels mit einem Polyamin ist, oder mindestens ein Detergenz ist, das ein boriertes, überbasifiziertes Natrium-, Calcium- oder Magnesiumcarboxylat oder Sulfonat ist.
  6. Zusammensetzung nach einem der vorstehenden Ansprüche, wobei (C) ausgewählt ist aus einem organischen Polysulfid, einem Metallthiophosphat, einem Phosphorsäureester oder einem Salz davon, einem Phosphit, einer phosphorhaltigen Carbonsäure, Ester, Ether oder Amid, einem Alkalimetallborat, einem borierten Fettsäureamin, einem borierten Phospholipid und einem Boratester.
  7. Zusammensetzung nach einem der Ansprüche 1 bis 5, wobei (C) ausgewählt ist aus einem organischen Polysulfid, einem Phosphorsäureester, hergestellt durch Umsetzen einer Dithiophosphorsäure mit einem Epoxid, um eine Zwischenstufe zu bilden, und wobei diese Zwischenstufe weiter mit einer phosphorhaltigen Säure oder einem Anhydrid umgesetzt wird, oder einem Salz des Phosphorsäureesters, einem Phosphorsäureester, hergestellt durch Umsetzen einer phoshorhaltigen Säure oder eines Anhydrids mit mindestens einem Alkohol, wobei jeder Alkohol unabhängig 1 bis 30 Kohlenstoffatome enthält, oder einem Salz des Phoshphorsäureesters, und einem Dihydrocarbyl- oder Trihydrocarbylphosphit, das unabhängig 1 bis 30 Kohlenstoffatome in jeder Hydrocarbylgruppe enthält.
  8. Zusammensetzung nach einem der vorstehenden Ansprüche, wobei die Zusammensetzung ein Getriebeöl ist.
  9. Verfahren zum Schmieren eines Sammelgetriebes, umfassend ein Einbringen der Schmierzusammensetzungen nach einem der Ansprüche 1 bis 8 in ein Sammelgetriebe und Betreiben des Sammelgetriebes.
EP95302545A 1994-04-19 1995-04-18 Schmiermittelzusammensetzungen mit hoher Oxidationsbeständigkeit die ein Dispergiermittel und ein Antioxidant enthalten Revoked EP0678569B1 (de)

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Cited By (2)

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US7871965B2 (en) 2003-04-25 2011-01-18 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
WO2014014561A1 (en) * 2012-07-18 2014-01-23 Chevron Oronite Company Llc Viscosity improver grafted with unsaturated acylating agent and an aryloxyalylkene monoamine

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CA2162438C (en) * 1994-11-15 2007-04-24 Betsy J. Butke Lubricants and fluids containing thiocarbamates and phosphorus esters
GB9516326D0 (en) * 1995-08-09 1995-10-11 Exxon Research Engineering Co Lubricant composition containing antioxidant additive combination
AU719520B2 (en) * 1995-09-19 2000-05-11 Lubrizol Corporation, The Additive compositions for lubricants and functional fluids
US5693598A (en) * 1995-09-19 1997-12-02 The Lubrizol Corporation Low-viscosity lubricating oil and functional fluid compositions
EP0856042B9 (de) * 1995-10-18 2011-12-21 Infineum USA L.P. Automatische getriebe mit getriebeflussigkeit mit verbesserter reibungdauerhaftigkeit
SG64414A1 (en) * 1996-01-16 1999-04-27 Lubrizol Corp Lubricating compositions
ZA97222B (en) * 1996-01-16 1998-02-18 Lubrizol Corp Lubricating compositions.
JP4334623B2 (ja) * 1996-06-12 2009-09-30 出光興産株式会社 自動変速機用潤滑油組成物
US6645920B1 (en) * 2002-11-14 2003-11-11 The Lubrizol Corporation Additive composition for industrial fluid
US8168572B2 (en) 2007-04-25 2012-05-01 Dow Global Technologies Llc Lubricant blend composition
DE102018006661A1 (de) 2018-08-23 2020-02-27 Klüber Lubrication München Se & Co. Kg Schmiermittelzusammensetzung

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GB1042635A (en) * 1962-06-28 1966-09-14 Ethyl Corp Functional fluids
US4612129A (en) * 1985-01-31 1986-09-16 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates and lubricating oils containing same
US4758362A (en) * 1986-03-18 1988-07-19 The Lubrizol Corporation Carbamate additives for low phosphorus or phosphorus free lubricating compositions
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5366648A (en) * 1990-02-23 1994-11-22 The Lubrizol Corporation Functional fluids useful at high temperatures
DE69323717T2 (de) * 1992-12-21 1999-07-01 Oronite Japan Ltd., Tokio/Tokyo Wenig Phosphor enthaltende Motorölzusammensetzungen und Zusatzzusammensetzungen

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7871965B2 (en) 2003-04-25 2011-01-18 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
WO2014014561A1 (en) * 2012-07-18 2014-01-23 Chevron Oronite Company Llc Viscosity improver grafted with unsaturated acylating agent and an aryloxyalylkene monoamine

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EP0678569A3 (de) 1996-04-03
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ES2194887T3 (es) 2003-12-01
ZA953079B (en) 1996-01-05
DE69529695D1 (de) 2003-04-03
AU1638595A (en) 1995-10-26
CA2147238C (en) 2009-10-06
CA2147238A1 (en) 1995-10-20
EP0678569A2 (de) 1995-10-25

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