[go: up one dir, main page]

EP0335701A2 - Schmierölzusammensetzung - Google Patents

Schmierölzusammensetzung Download PDF

Info

Publication number
EP0335701A2
EP0335701A2 EP89303122A EP89303122A EP0335701A2 EP 0335701 A2 EP0335701 A2 EP 0335701A2 EP 89303122 A EP89303122 A EP 89303122A EP 89303122 A EP89303122 A EP 89303122A EP 0335701 A2 EP0335701 A2 EP 0335701A2
Authority
EP
European Patent Office
Prior art keywords
ester
amide
acid
oil
amine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89303122A
Other languages
English (en)
French (fr)
Other versions
EP0335701A3 (de
Inventor
Armgard Kohler Everett
Edmund Frank Perozzi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Afton Chemical Corp
Original Assignee
Afton Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/281,262 external-priority patent/US4960530A/en
Priority claimed from US07/304,772 external-priority patent/US5028345A/en
Application filed by Afton Chemical Corp filed Critical Afton Chemical Corp
Publication of EP0335701A2 publication Critical patent/EP0335701A2/de
Publication of EP0335701A3 publication Critical patent/EP0335701A3/de
Withdrawn legal-status Critical Current

Links

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
    • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
    • 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
    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/68—Esters
    • 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
    • C10M133/16—Amides; Imides
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • 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
    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C10M135/06—Esters, e.g. fats
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • 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
    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
    • 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
    • C10M141/10—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 phosphorus-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
    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
    • 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
    • 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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • 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
    • C10M2215/08—Amides
    • 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
    • C10M2215/08—Amides
    • C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
    • 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
    • C10M2215/086—Imides
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • 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
    • C10M2215/12—Partial amides of polycarboxylic acids
    • C10M2215/122—Phtalamic acid
    • 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
    • C10M2215/26—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
    • C10M2215/28—Amides; Imides
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • 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
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbased sulfonic acid salts
    • 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
    • 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
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • 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
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10M2227/061—Esters derived from boron
    • 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
    • C10N2040/25—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
    • C10N2040/251—Alcohol-fuelled 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
    • C10N2040/255—Gasoline 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
    • C10N2040/255—Gasoline engines
    • C10N2040/28—Rotary 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
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates generally to lubricant oil compositions which contain additives to reduce friction and wear and inhibit deterioration of the oil and more specifically to such compositions which contain cosul­furized blends of certain organic esters, amines and amides which contain at least one and preferably two polar substituent groups.
  • the performance requirements for lubricants used in various applications such as internal combustion engine lubrication, gear lubrication, and functional fluids such as hydraulic and automatic transmission fluids are con­stantly being made more stringent by the manufacturers of products using these lubricants.
  • the smaller engines in use today require motor oils of higher over-all performance, such as with respect to reducing sludge for­mation.
  • One problem associated with formulating such high performance oils is the precipitation of ingredients due to a lack of compatibility of the various additives, espe­cially in the additive package concentrates which are used in making the finished oils.
  • the invention provides high performance lubricants with excellent friction, anti-wear and/or anti-sludge properties while minimizing such pre­cipitation.
  • a lubricant composition comprising an oil of lubricating viscosity, and a cosulfurized blend which includes (a) a carboxylic acid ester material and (b) an ester, amide, ester-amide or fatty amine derivative which contains at least one polar substituent group.
  • the deriva­tive contains two or more polar groups selected from hydroxyl and primary or secondary amino including combina­tions thereof.
  • novel cosulfurized blends which are useful in forming the above compositions which blends include a carboxylic acid ester material and an ester, amide, ester-amide or fatty amine derivative which con­tains at least one polar group and which is selected from the group consisting of:
  • Carboxylic acid ester materials suitable for prepar­ing the cosulfurized blends include C1-C20 alkyl esters of C8-C24 unsaturated fatty acids such as palmitoleic, oleic, ricinoleic, petroselinic, vaccenic, linoleic, linolenic, oleostearic, licanic, paranaric, tariric, gadoleic, arachidonic, and cetoleic.
  • fatty acid ester materials obtained from animal fats and veget­able oils such as tall oil, linseed oil, olive oil, castor oil, peanut oil, rope oil, fish oil, sperm oil, coconut oil, lard oil, soybean oil and mixtures thereof, can also be used in the present invention.
  • Exemplary fatty esters include lauryl tallate, methyl oleate, ethyl oleate, lauryl oleate, cetyl oleate, cetyl linoleate, lauryl ricinoleate, oleyl linoleate, oleyl stearate, and alkyl glycerides.
  • the fatty esters can contain other substituents such as hydroxyl or sulfo which can be naturally occurring, for example ricinoleic (12-hydroxyoleic) acid or introduced into the carbon chain such as by reaction with sulfur trioxide.
  • Sulfurized fatty acid ester materials can also be used in preparing the blends.
  • the sulfurized fatty acid ester materials are prepared by reacting sulfur, sulfur monochloride, and/or sulfur dichloride with the fatty ester under elevated temperatures.
  • a specific example of a useful sulfurized carboxylic acid ester material comprises sulfurized, transesterified, triglycerides derived from fatty acids and fatty oils (e.g., oils selected from coconut, lard, tallow, palm, soybean, and peanut oils and mixtures thereof). Examples of such material are disclosed in U. S. patent 4,380,499.
  • the acid moiety of the triglycerides disclosed in the patent consists of an acid mixture having no more than about 65 mole % unsaturated acids, mainly mono-unsaturated, and no less than about 35 mole % saturated aliphatic acids. Of the total acid moiety, less than about 15 mole % are saturated acids having 18 or more carbon atoms and more than about 20 mole % are saturated acids having 6 to 16 carbon atoms including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms. Less than about 15 mole % are poly-unsaturated acids and more than about 20 mole % are mono-unsaturated acids. Solubilizing agents such as unsaturated esters and olefins can be incorporated in the material. Such materials are commer­cially available, for example, from Keil Chemical Divi­sions of Ferro Corporation under the trademark SUL-PERM® 307.
  • organic acid as used herein includes aliphatic carboxylic acids, organic phosphorus acids, and organic sulfur acids.
  • Examples of the types of organic acid ester, amide and ester-amide derivatives suitable for use in conjunc­tion with the carboxylic acid ester material to form the cosulfurized blends include:
  • the fatty acid moiety can be sulfurized.
  • sulfurized compounds can be made by reacting a sulfurized fatty acid with an oxyalkylated amine (e.g., diethanolamine) as disclosed, for example, in U.S. patent 4,201,684.
  • Sulfurized fatty acids can be made by heating a mixture of fatty acid with elemental sulfur at temperatures of from 100 to 250°C. with or without a catalyst such as 2,5-dimercapto-1,3,4,thiadiazole (DMTD) as known in the art.
  • DMTD 2,5-dimercapto-1,3,4,thiadiazole
  • Another method is to first make the fatty acid ester, amide or ester-amide by reacting a fatty acid with an oxyalkylated amine (e.g., diethanolamine) as disclosed, for example, in U.S. patent 4,208,293, and then reacting that intermediate with elemental sulfur at elevated temperature (e.g., 100° to 250°C.) with or without a catalyst such as DMTD.
  • an oxyalkylated amine e.g., diethanolamine
  • ester, ester-amide, and amide components can be separated by distillation and used separately in lubricat­ing oil compositions or they can be used as mixtures.
  • mixtures of fatty acid and dialkanolamine are reacted, very little ester-amide forms and the product contains mainly amide because of the greater reactivity of the HN ⁇ group.
  • ester-amide can form.
  • the preferred amines used to make the compounds are alkoxylated amines such as methanolamine, ethanolamine, dimethanolamine, diethanolamine, 2-isopropanolamine and the like. As stated previously, these can be reacted to form both amides, esters and ester-amides.
  • alkoxylated amines such as methanolamine, ethanolamine, dimethanolamine, diethanolamine, 2-isopropanolamine and the like.
  • these can be reacted to form both amides, esters and ester-amides.
  • sulfurized oleic acid, (S)oleic reacts as follows:
  • the compounds can be further reacted with alkylene oxide as described in U. S. 4,201,684 to form a polyoxy­alkylene chain [(R′-O) n as defined above in the formula for the amine where R′ contains 2-4 carbons n>1].
  • Pre­ferred fatty acids used in making the amide, ester, ester-amide compounds are those containing 8-20 carbon atoms.
  • hypogeic acid examples include hypogeic acid, oleic acid, linoleic acid, elaidic acid, abietic acid, dihydroabietic acid, dehydroabietic acid, tall oil fatty acids, erucic acid, brassidic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecoic acid, myristic acid, palmitic acid, stearic acid, arachidic acid and mixtures thereof.
  • the fatty acid component is a mixture of acids derived from coconut oil.
  • B. Fatty acid amides of polyamines represented by the formula: NH2(CH2) n -(NH(CH2) n ) m -NH2 where n 2 or 3 and m is 0 to 10.
  • suitable amines include ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, and pentaethylene hexamine.
  • Preferred fatty acids are those described in (A) above which can be sulfurized.
  • the fatty acid amides can be prepared by reacting the fatty acid with the amine as known in the art. For example, oleic acid with diethylene triamine as follows: Oleic acid + NH2(CH2)2-NH-(CH2)2NH2- ⁇ oleyl NH(CH2)2NH(CH2)2NH2NH2
  • Fatty acid partial esters of polyhydric alcohols which preferably contain 2 to 4 free hydroxyl groups.
  • Suitable polyhydric alcohols for forming the esters contain 3 to 6 hydroxyl groups and include, for example, glycerol, diglycerol, pentaerythritol, trimethyl­olethane, trimethylolpropane, 1,2,4-butanetriol, 1,2,6-­hexanetriol, sorbitol and mannitol and the like.
  • the esters are formed by reacting the polyhydric alcohol with a fatty acid such as described in (A) above at mole ratios to provide a partial ester which contains at least one and preferably two or more free hydroxyl groups.
  • a preferred ester is glycerol monooleate which is commercially avail­able.
  • the glycerol esters can also be obtained by partial saponification of fatty oils.
  • Oxyalkylated derivatives can also be used such as are formed by the reaction of glycerol monooleate with ethylene oxide.
  • amide and ester compounds can be formed, for example, by reacting the amine or alcohol with an acid chloride of a dialkyl phosphorus acid of the formula: where R, and R ⁇ are independently selected from hydro­carbyl radicals containing from 4 to 20 carbons and X is selected from oxygen and sulfur including various combina­tions thereof.
  • the hydrocarbyl group is preferably selected from C8-C20 alkyl or alkenyl to provide oil solubility.
  • the dialkyl phosphorus acids can be prepared, for example, by reacting one or more alcohols, containing 4 to 20 carbons, such as n-butanol, isobutanol, t-butanol, 2-butanol, pentanol, hexanol, cyclohexanol, 2-ethylhexanol, 1-decanol, 1-do­decanol, cetyl alcohol, and stearyl alcohol with an inorganic phosphorus acid anhydride such as phosphorus pentoxide or phosphorus pentasulfide as is known in the art.
  • the acid chlorides can be prepared by reaction of the acid with chlorine as known in the art, for example: (C2H5O)2 H + Cl2 ⁇ (C2H5O)2 -Cl + HCl
  • the amine derivatives which can also be considered as being esters of the phosphorus acid can be prepared by reacting a dialkylphosphate with formaldehyde and a di­alkanol amine, for example, as follows:
  • E Sulfonamides and esters of alkylsulfonic acids with (1) oxyalkylated amines as described in (A) above, (2) polyamines as described in (B) above, and (3) poly­hydric alcohols as described in (D) above.
  • the alkyl group of the sulfonic acid generally contains from 4 to 50 carbons, and preferably at least 8 carbons for oil solu­bility, and can be a straight or branched chain.
  • Suitable alkyl groups include polyalkenes such as polyisobutylene (PIB) having a molecular weight, M n , of from 250 to 5000.
  • PIB polyisobutylene
  • Sulfonamides can be formed by reacting the corre­sponding sulfonyl chloride with the amine or alcohol for example as follows: C8H17OH + SOCl2 ⁇ C8H17O Cl + HCl C8H17O Cl + HN(CH2CH2OH)2 ⁇ C8H17O N(CH2CH2OH)2 + HCl
  • Other derivatives can be prepared by reacting alkylenes or alcohols with sulfur trioxide to form a sulfonic acid intermediate which is then reacted with an amine, for example as follows: polyisobutylene (PIB) + SO3 ⁇ PIB-SO3H PIB-SO3H + HN(CH2CH2OH)2 ⁇ PIB-SO2N(CH2CH2OH)2 C8H17OH + SO3 ⁇ C8H17OSO3H C8H17OSO3H + HN(CH2CH2OH)2 ⁇ C8H17OSO2N(CH
  • Suitable fatty amines for use in the invention include fatty amines of the formula: wherein R is an aliphatic hydrocarbon group containing 12-36 carbon atoms, R′ is a divalent aliphatic hydrocarbon radical containing 1-4 carbon atoms, R ⁇ is a divalent aliphatic hydrocarbon radical containing 1-4 carbon atoms (preferably 2-4), n is an integer from 0 to 20, preferably 1-10, and R′′′ is selected from hydrogen and the group -R′O(R ⁇ -O) n -H. Examples of such amines are described, for example in U. S. patent 4,231,883.
  • Such amines include N,N-bis(2-hydroxyethyl)-oleylamine, N,N-bis(2-­hydroxyethoxyethyl)-1-methyl-undecylamine, and N-(2-­hydroxyethyl)-N-(2-hydroxyethoxyethyl)-n-dodecylamine.
  • esters and amides of the organic acids which contain at least one polar substituent group can also be used provided they have sufficient solubility in oils when cosulfurized with the fatty acid ester materials.
  • the derivatives can be sulfurized prior to cosulfurization but this is not necessary.
  • the materials which are useful in forming the cosulfurized blends with fatty acid esters and especially the diol containing materials can be further reacted with a boronating agent such as boron acids, e.g., H3PO3, and boron oxides, e.g., B2O3, and such boronated materials are considered to be within the scope of this invention.
  • a boronating agent such as boron acids, e.g., H3PO3, and boron oxides, e.g., B2O3, and such boronated materials are considered to be within the scope of this invention.
  • the carboxylic acid ester material and the fatty amine, organic acid ester, amide and ester-amide derivative are mixed in proportions of from 20 to 80 percent by weight of carboxylic acid ester material and from 80 to 20 percent by weight of the fatty amine, organic ester and/or amide derivative (preferably in a range of 40-60 percent of each component) based on the weight of the mixture, and then heated with from 1 to 10 percent by weight of elemental sulfur based on the total weight of mixture at a tempera­ture of from 100° to 250°C. and preferably from 140° to 180°C. with or without a catalyst for from 1/2 to 2 hours.
  • Suitable catalysts as known in the art include 2,5-dimercapto- 1,3,4-thiadiazole DMTD and alkyl amines such as PRIMENE® 81-R (RC(CH3)2NH2 where R is C12-C14).
  • the cosulfurized mixtures preferably contain from 2 to 10 percent by weight sulfur and most preferably from 5 to 7 percent by weight with the amount of elemental sulfur in the reaction being adjusted to provide the desired sulfur content.
  • a composition according to the Class A compounds is commercially available. It contains about 6 weight percent sulfur, and consists essentially of a high tempera­ture blend having a common sulfur linkage of sulfurized esters of mixed animal and vegetable oils comprising transesterified triglycerides containing a mixture of saturated and mono- and polyunsaturated monobasic acids in which most of the free acid has been esterified with mono-alcohols (approximately 60% by weight) as disclosed in U.S.
  • cosulfurized blends can be used in mineral oil or in synthetic oils of suitable viscosity for the desired lubricant application.
  • Crankcase lubricating oils have a viscosity up to about 80 SUS at 210°F.
  • crankcase lubricating oils for use in the invention have a viscosity up to about SAE 40. Sometimes such motor oils are given a classification at both 0° and 210°F., such as SAE 10W or SAE 5W30.
  • Mineral oils include those of suitable viscosity refined from crude oil from all sources including Gulf coasts, midcontinent, Pennsylvania, California, Alaska and the like. Various standard refinery operations can be used in processing the mineral oil.
  • Synthetic oil includes both hydrocarbon synthetic oil and synthetic esters.
  • Useful synthetic hydrocarbon oils include polymers of alpha-olefins having the proper viscosity. Especially useful are the hydrogenated liquid oligomers of C6 ⁇ 12 alpha-olefins such as alpha-decene trimer. Likewise, alkylbenzenes of proper viscosity can be used, such as didodecylbenzene.
  • Useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acid as well as monohydroxy alkanols and polyols. Typical examples are didodecyl adipate, trimethylol propane tripelargonate, pentaerythritol tetracaproate, di-(2-ethylhexyl)adipate, dilauryl sebacate and the like. Complex esters prepared from mixtures of mono- and dicarboxylic acid and mono- and polyhydroxyl alkanols can also be used.
  • Blends of mineral oil with synthetic oil are also useful. For example, blends of 5-25 wt.% hydrogenated alpha-decene trimer with 75-95 wt.% 150 SUS (100°F.) mineral oil. Likewise, blends of 5-25 wt.% di-(2-­ethylhexyl)adipate with mineral oil of proper viscosity results in a useful lubricating oil. Also, blends of synthetic hydrocarbon oil with synthetic esters can be used. Blends of mineral oil with synthetic oil are useful when preparing low viscosity oil (e.g. SAE 5W30) since they permit these low viscosities without contributing excessive volatility.
  • low viscosity oil e.g. SAE 5W30
  • the amounts of cosulfurized blend in the lubricat­ing oil generally range from 0.05 to 6.0 percent by weight for crankcase applications (preferred .3 to 3.5) based on the total weight of lubricating oil composition although larger amounts can be used depending upon the application, e.g. up to about 20 percent by weight.
  • the lubricating oil compositions of the present invention for crankcase use preferably contain an over­based alkaline earth metal sulfonate, zinc dithiophosphate and an ashless dispersant. They can also contain any of the other additives conventionally added to such composi­tions such as, for example, wear-inhibiters, friction reducers, viscosity index improvers, antioxidants, dispersants, detergents such as neutral alkaline earth metal sulfonates, antifoam agents, pour point depressants and the like provided, of course, that the presence of such additional additives in the compositions does not significantly interfere with the benefits provided by the additives of the present invention.
  • any of the other additives conventionally added to such composi­tions such as, for example, wear-inhibiters, friction reducers, viscosity index improvers, antioxidants, dispersants, detergents such as neutral alkaline earth metal sulfonates, antifoam agents, pour point depressants and the like provided, of course
  • a combination of overbased alkaline earth metal sulfonate and zinc dihydrocarbyl dithiophosphate along with the cosulfurized materials provide enhanced anti-wear properties.
  • the combination of an ashless dispersant and the cosulfurized blends of the invention provide synergis­tic anti-sludge properties.
  • Suitable overbased alkaline earth metal sulfonates have a base number of at least 100, more preferably at least about 300.
  • the "total base number” (TBN) also referred to as “base number” is a measure of the alkaline reserve in the product in terms of its stoichiometric equivalent of mg KOH per gram of product (ASTM D2896).
  • Overbased alkaline earth metal sulfonates are derived from sulfonic acids, particularly from petroleum sulfonic acids, polyalkylene sulfonic acids or alkylated benzene sulfonic acids.
  • Useful sulfonic acids from which the overbased alkaline earth metal sulfonates are prepared have an average molecular weight of 250-5000, more pre­ferably 400-1100, and most preferably 440-600.
  • Examples of specific sulfonic acids include mahogany sulfonic acids, petrolatum sulfonic acids, aliphatic sulfonic acids and cycloaliphatic sulfonic acids.
  • the sulfonic acids are alkaryl sulfonic acids such as alkylbenzene or alkylnaphthalene sulfonic acids.
  • Suitable alkyl groups contain from 10 to 30 carbon atoms or more.
  • higher molecular weight alkyls derived from alkylation with polyolefin (e.g., polybutenes) having molecular weights up to about 2000 can be used to give hydrocarbyl sulfonic acids somewhat above the preferred range, but still useful.
  • Preferred sulfonic acids are the alkaryl sulfonic acids also referred to as alkylbenzene sulfonic acids.
  • Alkaryl sulfonic acids can be made by conventional methods such as by alkylating benzene, toluene or naphtha­lene or aromatic mixtures with olefins containing 10-30 carbon atoms or more (e.g., with polyolefin).
  • the most suitable olefins are cracked-wax olefins, propylene trimers and tetramers and olefin mixtures derived from aluminum alkyl chain growth.
  • Alkylation is effected using a Friedel-Crafts (e.g., AlCl3 or BF3) catalyst.
  • the alkylaromatic mixture contains predominantly mono- and di-alkyl products.
  • These alkyl aromatics are then sulfonated by known methods such as by reaction with sulfuric acid, oleum, sulfur trioxide and the like.
  • preferred sulfonic acids include octadecyl­benzene sulfonic acid, didodecylbenzene sulfonic acid, docosylbenzene sulfonic acid, triacontylbenzene sulfonic acid, dodecyloctadecyl-benzene sulfonic acid, didecylben­zene sulfonic acid, dodecylnaphthalene sulfonic acid, hexadecylnaphthalene sulfonic acid, dinonylbenzene sulfonic acid and mixtures thereof and the like.
  • the hydrocarbyl sulfonic acids preferably have an average molecular weight of 250-5000. More preferred are the alkylbenzene sulfonic acids having an average molecular weight of 400-1100 and most preferably 440-600.
  • the overbased alkaline earth metal sulfonates are produced by neutralizing the sulfonic acid with an alkaline earth metal base to form an alkaline earth metal sulfonate salt and then overbasing the alkaline earth metal sulfonate with the corresponding alkaline earth metal carbonate.
  • the process is conducted to give a total base number of at least 100, more preferably at least 300. There is no real maximum on total base number, but for practical purposes they seldom exceed about 550.
  • Overbased calcium petroleum sulfonates or alkaryl (e.g., alkylbenzene) sulfonates are especially preferred. These are prepared by neutralizing the corresponding petroleum sulfonic acid or alkylated benzene sulfonic acid with a calcium base to form a calcium sulfonate salt and the overbasing the calcium sulfonate with calcium carbonate generally by passing carbon dioxide through a mixture of the neutral calcium sulfonate, mineral oil, lime and water.
  • an overbased calcium sulfonate produced from a synthetic benzene sulfonic acid having a TBN of 310 can be obtained from Ethyl Petroleum Additives, Inc. under the designation HiTEC® 611.
  • ZDDP zinc dihydrocarbyldithiophosphates
  • ZDDP zinc dihydrocarbyldithiophosphates
  • a typical alkyl-type ZDDP contains a mixture of isobutyl and isoamyl groups.
  • Zinc dinonylphenyldithio­phosphate is a typical aryl-type ZDDP.
  • Preferred zinc dithiophosphate components are represented by the formula: in which R is a hydrocarbyl radical having from 3 to 12 carbon atoms.
  • the most preferred zinc dithiophosphates are those in which R represents an alkyl radical having from 3 to 8 carbon atoms such as isopropyl, isobutyl, isoamyl and 2-ethylhexyl.
  • suitable compounds include zinc isobutyl 2-ethyl­hexyl dithiophosphate, zinc di(2-ethylhexyl)dithiophosphate, zinc isopropyl 2-ethylhexyl dithiophosphate, zinc isoamyl 2-ethylhexyl dithiophosphate and zinc dinonylphenyldithio­phosphate.
  • Such additives are also available commercially.
  • a mixed 2-ethylhexyl, 2-methylpropyl, iso­propyl ester of phosphorodithioic acid, zinc salt can be obtained from Ethyl Petroleum Additives, Inc. under the designation HiTEC® 685.
  • crankcase oils also contain an ashless dispersant such as the polyolefin-substituted succinamides and succinimides of polyethylene polyamines such as tetraethylenepentamine.
  • the polyolefin succinic substituent is preferably a polyisobutene group having a number average molecular weight of from 800 to 5,000 and preferably from 1,000 to 2,000.
  • Such ashless dispersants are more fully described in U.S. Pat. No. 3,172,892, U.S. Pat. No. 3,219,666 and U.S. Pat. No. 4,234,435.
  • ashless dispersants are the polyolefin succinic esters of mono-and polyhydroxyl alcohols containing 1 to about 40 carbon atoms. Such dispersants are described in U.S. Pat. No. 3,381,022 and U.S. Pat. No. 3,522,179.
  • mixed ester/amides of polyolefin sub­stituted succinic acid made using alkanols, amines and/or aminoalkanols represent a useful class of ashless dis­persants.
  • the succinic amide, imide and/or ester type ashless dispersants may be boronated by reaction with a boron compound such as boric acid.
  • the succinic amide, imide and/or ester may be oxyalkylated by reaction with an alkylene oxide such as ethylene oxide or propylene oxide.
  • ashless dispersants include the Mannich condensation products of polyolefin-substituted phenols, formaldehyde and polyethylene polyamine.
  • the poly olefin phenol is a polyisobutylene-­substituted phenol in which the polyisobutylene group has a molecular weight of from about 800 to 5,000.
  • the pre­ferred polyethylene polyamine is tetraethylene pentamine.
  • Mannich ashless dispersants are more fully described in U.S. Pat. No. 3,368,972; U.S. Pat. No. 3,413.347; U.S. Pat. No. 3,442,808; U.S. Pat. No. 3,448,047; U.S. Pat.
  • the above Mannich dispersants can be reacted with boric acid to form boronated dispersants having improved corrosion properties.
  • Viscosity index improvers can be included such as the polyalkylmethacrylate type or the ethylene-propylene copolymer type including graft copolymers with an N-allyl amide such as diallyl formamide.
  • styrene-diene VI improvers or styrene-acrylate copolymers can be used.
  • Alkaline earth metal salts of phosphosulfurized polyiso­butylene are useful.
  • a homogeneous blend of the foregoing active components is achieved by merely blending the components separately, together or in any combination or sequence with the lubricating oil in a determined proportion sufficient to provide the lubricat­ing oil composition with the desired properties. This is normally carried out at ambient temperature to 70°C.
  • the selection of the particular base oil and components, as well as the amounts and ratios of each depends upon the contemplated application of the lubricant and the presence of other additives.
  • the amount of overbased alkaline earth metal sulfonate in the lubricat­ing oil can vary from 0.5 to 5.0, and usually from 0.75 to 2.5 weight percent based on the weight of the final com­position.
  • the amount of zinc dihydrocarbyl dithiophos­phate in the lubricating oil can vary from 0.5 to 3.0, and usually from 1.0 to 2.0 weight percent based on the weight of the final composition.
  • the amount of ashless disper­sant in the lubricating oil can vary from 2 to 8, and usually from 3 to 6 weight percent based on the weight of the final composition.
  • the amount of cosulfurized blend in the lubricating oil can vary from 0.05 to 6.0, and usually from 0.3 to 3.5 weight percent based on the weight of the final composition.
  • a preferred way to add the additives to lubricating oil is in the form of an additive package.
  • a diluent such as mineral oil, synthetic hydrocarbon oils and mixtures thereof which, when added to a base oil, will provide an effective concentration of the present additives and other known conventional additives such as those listed above.
  • the various additives are present in a proper ratio such that when a quantity of the concentrate is added to lubricating oil the various additives are all present in the proper concentration.
  • the additive pack will contain 2.0 wt.% of that particular additive component.
  • the concentrate will be 95.0 to 99.9 percent by weight additive composition and from 5.0 to 0.1 percent by weight lubricating oil diluent.
  • the additive composition comprises 97 to 99 percent by weight of the lubricating oil additive concen­trate.
  • This concentrate is diluted with additional lubri­cating oil before use such that the finished lubricating oil product contains from 5.0 to 25.0 percent by weight of concentrate. Accordingly, typical amounts of ashless dispersant in a concentrate would range from 40 to 60 weight percent of total concentrate and typical amounts of ZDDP or overbased alkaline earth metal sulfonate would range from 10 to 20 weight percent of total concentrate.
  • a mixture of 60 grams of coconut oil fatty acid diethanol amide (Schercomid® SCO - extra), 90 grams of soybean oil, 9.57 grams of sulfur and 0.80 gram of 2,5-­dimercapto-1,3,4-thiadiazole (DMTD) as catalyst are heated at about 160°C. for 30 minutes with stirring while allowing water vapor to escape and then cooled to avoid amide reactions.
  • the product contains 6% by weight sulfur.
  • a mixture of 60 grams of glycerol monooleate, 90 grams of coconut oil, 9.57 grams of sulfur and 0.80 gram of DMTD as catalyst are heated at about 160° C. for about 2 hours with stirring. About 159 grams of product is recovered and filtered to remove a small amount of dark precipitate.
  • a mixture of 60 grams of glycerol monooleate, 90 grams of soybean oil, 9.57 grams of sulfur and 0.80 gram of DMTD as catalyst are heated at about 160°C. for 30 minutes with stirring. About 157 grams of product is recovered.
  • a reaction product of glycerol monooleate and ethylene oxide is prepared by mixing 3.0 grams of catalyst (Amberlyst® 15 Mallinckrodt) and 150 grams of glycerol monooleate in a flask equipped with a stirrer, gas inlet tube, dry ice-isopropyl alcohol condenser and thermometer and heated to 100°C. Ethylene oxide is fed to the reac­tion mixture through the gas inlet tube for about 3 hours at temperatures of from about 40° to 107°C. The weight increase of the reaction mixture is about 5.2 grams indicating the combination of that amount of ethylene oxide with the glycerol monooleate. The product is filtered and cosulfurized with soybean oil according to the following procedure.
  • the di-2-ethylhexylphosphorodiethanol amide can then be reacted with a fatty oil such as soybean or coconut oil and elemental sulfur as described in the foregoing examples to form a cosulfurized blend.
  • a fatty oil such as soybean or coconut oil and elemental sulfur as described in the foregoing examples to form a cosulfurized blend.
  • the sulfur analog, di-2-ethylhexyl-di­thiophosphorochloridate can be prepared, reacted with diethanol amine to form the amide and then cosulfurized with soybean or coconut oil.
  • a reaction product of amine and fatty acid can be prepared by heating (180°-200°C) a mixture of 100 grams, .538 mole, of coconut oil fatty acid and 55.4 grams, .538 mole of diethylene triamine.
  • the product is expected to be a mixture of primary and secondary amides.
  • the product can then be cosulfurized by reaction with sulfur and soybean or coconut oil following the procedures described in the foregoing examples.
  • Zinc dialkyldithiophosphate 0.5-3.0 parts
  • SUL-PERM® 60-93 0.05-6.0 parts.
  • the lubricity or wear properties of the lubricating oil compositions of the present invention were determined in the 4-Ball Wear Test. This test is conducted in a device comprising four steel balls, three of which are in contact with each other in one plane in a fixed triangular position in a reservoir containing the test sample. The fourth ball is above and in contact with the other three. In conducting the test, the upper ball is rotated while it is pressed against the other three balls while pressure is applied by weight and lever arms. The diameter of the scar on the three lower balls is measured by means of a low power microscope, and the average diameter measured in two directions on each of the three lower balls is taken as a measure of the anti-wear characteristics of the oil. A larger scar diameter means more wear.
  • Blend A Base oil containing 1.2 wt.% zinc dialkyldithiophosphate (HiTEC® 685).
  • Blend B Base oil containing 1.3 wt.% overbased calcium alkylbenzene sulfonate, TBN 310 (HiTEC® 611).
  • Blend C Base oil containing 0.5% wt.% SUL-PERM® 60-93.
  • Blend D Base oil containing 1.2 wt.% zinc dialkyldithiophosphate (HiTEC® 685) + 0.5 wt.% SUL-PERM® 60-93.
  • Blend E Base oil containing 1.2 wt.% zinc dialkyldithiophosphate (HiTEC® 685) + 1.3 wt.% overbased calcium alkylbenzene sulfonate, TBN 310 (HiTEC® 611).
  • Blend F Base oil containing 1.3 wt.% overbased calcium alkylbenzene sulfonate, TBN 310 (HiTEC® 611) + 0.5 wt.% SUL-PERM® 60-93.
  • Blend G Base oil containing 1.2 wt.% zinc dialkyldithiophosphate (HiTEC® 685) + 1.3 wt.% overbased calcium alkylbenzene sulfonate, TBN 310 (HiTEC® 611) + 0.5 wt.% SUL-PERM® 60-93.
  • Blend G contain­ing all three of the above components gave a scar diameter significantly less than the other blends.
  • the additive combinations of the present invention are also deemed to impart detergency properties to lubricating oils containing same so as to inhibit sludge formation.
  • suitable amounts of the blend to inhibit sludge range from 0.05 to 6 percent by weight based on the total weight of lubricating oil composition (preferred 0.3 to 3.5 weight percent).
  • Additive concen­trates generally contain from 2 to 25 percent by weight of such high temperature blend.
  • Blends A′, B′, and C′ are fully formulated 5W30 oils made by combining a base oil with zinc dialkyldithiophosphate ester (ZDDP) antiwear, neutral and overbased calcium sulfonate detergents, alkenylsuccin­imide ashless dispersant, antioxidants, antifoam agent pour point depressant, viscosity index (VI) improver and, in Blend C′ a rust inhibitor.
  • Blend D is a fully formulated SAE 30 oil which is made from a base oil containing the above additives except for the VI improver and rust inhibitor.
  • the co-sulfurized mixture of Schercomid SCO-extra and soybean oil showed only a trace of haze after 28 days at room temperature and was clear at 70°C after 28 days.
  • the data are recorded in the following table in which the parenthetical amounts represent the weight percent addi­tive.
  • An oil blend corresponding to Blend G above was formulated except that the SUL-PERM® 60-93 was replaced by 0.5 weight percent of the cosulfurized glycerol monooleate soybean oil product prepared according to the process described in Example 3. When tested in the 4-ball wear test, the oil blend gave a wear scar diameter of 0.383 mm.
  • An oil additive concentrate was made which contained 5% by weight of the cosulfurized blend prepared according to Example 3 and also, besides the ZDDP anti-wear agent, neutral and overbased calcium sulfonate detergents, anti-­oxidants, anti-foam agent and process oil, about 60% by weight of a 1500 molecular weight succinimide dispersant.
  • Blend G An oil blend corresponding to Blend G above was formulated except that the SUL-PERM® 60-93 was replaced by 0.5 gram of the cosulfurized blend of glycerol monooleate-­ethylene oxide and soybean oil prepared according to the process described in Example 4. When tested in the 4-ball wear test, the oil blend gave a wear scar diameter of 0.371 mm. A fully formulated oil which contained .5% by weight of the cosulfurized blend in place of the blend of Example 3 was tested in the VE sludge test and gave a result of 58.1 compared to 77.6 for the control.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP89303122A 1988-03-31 1989-03-30 Schmierölzusammensetzung Withdrawn EP0335701A3 (de)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US17576188A 1988-03-31 1988-03-31
US175761 1988-03-31
US07/281,262 US4960530A (en) 1988-03-31 1988-12-07 Lubricating oil composition
US281262 1988-12-07
US07/304,772 US5028345A (en) 1988-12-07 1989-01-31 Lubricating oil composition
US304772 1989-01-31

Publications (2)

Publication Number Publication Date
EP0335701A2 true EP0335701A2 (de) 1989-10-04
EP0335701A3 EP0335701A3 (de) 1989-12-13

Family

ID=27390591

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89303122A Withdrawn EP0335701A3 (de) 1988-03-31 1989-03-30 Schmierölzusammensetzung

Country Status (3)

Country Link
EP (1) EP0335701A3 (de)
JP (1) JP2749623B2 (de)
CA (1) CA1325420C (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992002602A1 (en) * 1990-07-31 1992-02-20 Exxon Chemical Patents Inc. Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
US5282990A (en) * 1990-07-31 1994-02-01 Exxon Chemical Patents Inc. Synergistic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
EP0608018A1 (de) * 1993-01-22 1994-07-27 Akzo Nobel N.V. Aminoalkylphosphonat als Verschleissschutzadditiv für Schmiermittel mit einem hydrophilen Grundöl
EP0814148A2 (de) * 1992-12-21 1997-12-29 Oronite Japan Limited Motorölzusammensetzungen mit niedrigem Phosphorgehalt, und Zusatzzusammensetzungen
US7550415B2 (en) 2004-12-10 2009-06-23 Shell Oil Company Lubricating oil composition
US7741258B2 (en) 2006-02-21 2010-06-22 Shell Oil Company Lubricating oil composition
US8703680B2 (en) 2010-11-24 2014-04-22 Chevron Oronite Company Llc Lubricating composition containing friction modifier blend
US12173247B2 (en) 2020-12-16 2024-12-24 Huntsman Petrochemical Llc Reaction product of an organic amine and glycidol and its use as a friction modifier

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040192565A1 (en) * 2003-03-28 2004-09-30 Thiel C. Yvonne Lubricating oil compositions and methods for improving fuel economy in an internal combustion engine using same
US20120247412A1 (en) * 2011-03-31 2012-10-04 Chevron Oronite Company Llc Method for improving fuel economy of a heavy duty diesel engine

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2009296A1 (de) * 1968-05-24 1970-01-30 Mobil Oil Corp
DE2166893A1 (de) * 1971-03-12 1976-08-12 Rhein Chemie Rheinau Gmbh Schwefelhaltiges umsetzungsprodukt, verfahren zu seiner herstellung und verwendung als zusatz zu schmiermitteln
US4170560A (en) * 1976-04-01 1979-10-09 Chevron Research Company Lubricating oil antioxidant additive composition
GB2023169A (en) * 1978-06-14 1979-12-28 Lubrizol Corp Concentrates lubricant composotions and mathods for improving fuel economy of internal combustion engines
EP0009701A1 (de) * 1978-09-28 1980-04-16 RHEIN-CHEMIE RHEINAU GmbH Schwefelhaltige Umsetzungsprodukte, Verfahren zu ihrer Herstellung und Verwendung als Zusatz zu Schmiermitteln
US4201684A (en) * 1978-11-13 1980-05-06 Ethyl Corporation Lubricant composition of improved friction reducing properties
EP0060455A1 (de) * 1981-03-14 1982-09-22 BASF Aktiengesellschaft Inhibitoren gegen die Korrosion von CO2 und H2S in Wasser-in-Öl-Emulsionen

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2009296A1 (de) * 1968-05-24 1970-01-30 Mobil Oil Corp
DE2166893A1 (de) * 1971-03-12 1976-08-12 Rhein Chemie Rheinau Gmbh Schwefelhaltiges umsetzungsprodukt, verfahren zu seiner herstellung und verwendung als zusatz zu schmiermitteln
US4170560A (en) * 1976-04-01 1979-10-09 Chevron Research Company Lubricating oil antioxidant additive composition
GB2023169A (en) * 1978-06-14 1979-12-28 Lubrizol Corp Concentrates lubricant composotions and mathods for improving fuel economy of internal combustion engines
EP0009701A1 (de) * 1978-09-28 1980-04-16 RHEIN-CHEMIE RHEINAU GmbH Schwefelhaltige Umsetzungsprodukte, Verfahren zu ihrer Herstellung und Verwendung als Zusatz zu Schmiermitteln
US4201684A (en) * 1978-11-13 1980-05-06 Ethyl Corporation Lubricant composition of improved friction reducing properties
EP0060455A1 (de) * 1981-03-14 1982-09-22 BASF Aktiengesellschaft Inhibitoren gegen die Korrosion von CO2 und H2S in Wasser-in-Öl-Emulsionen

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992002602A1 (en) * 1990-07-31 1992-02-20 Exxon Chemical Patents Inc. Synergystic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
US5282990A (en) * 1990-07-31 1994-02-01 Exxon Chemical Patents Inc. Synergistic blend of amine/amide and ester/alcohol friction modifying agents for improved fuel economy of an internal combustion engine
EP0814148A2 (de) * 1992-12-21 1997-12-29 Oronite Japan Limited Motorölzusammensetzungen mit niedrigem Phosphorgehalt, und Zusatzzusammensetzungen
EP0814148A3 (de) * 1992-12-21 1998-01-14 Oronite Japan Limited Motorölzusammensetzungen mit niedrigem Phosphorgehalt, und Zusatzzusammensetzungen
EP0608018A1 (de) * 1993-01-22 1994-07-27 Akzo Nobel N.V. Aminoalkylphosphonat als Verschleissschutzadditiv für Schmiermittel mit einem hydrophilen Grundöl
US7550415B2 (en) 2004-12-10 2009-06-23 Shell Oil Company Lubricating oil composition
US7741258B2 (en) 2006-02-21 2010-06-22 Shell Oil Company Lubricating oil composition
US8703680B2 (en) 2010-11-24 2014-04-22 Chevron Oronite Company Llc Lubricating composition containing friction modifier blend
US12173247B2 (en) 2020-12-16 2024-12-24 Huntsman Petrochemical Llc Reaction product of an organic amine and glycidol and its use as a friction modifier

Also Published As

Publication number Publication date
CA1325420C (en) 1993-12-21
JPH01304185A (ja) 1989-12-07
JP2749623B2 (ja) 1998-05-13
EP0335701A3 (de) 1989-12-13

Similar Documents

Publication Publication Date Title
US4455243A (en) Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same
US4163729A (en) Synergistic combinations of hydrated potassium borate, antiwear agents, and organic sulfide antioxidants
US5403501A (en) Universal driveline fluid
US5858929A (en) Composition for providing anti-shudder friction durability performance for automatic transmissions
US5256320A (en) Grease compositions
EP1805286B1 (de) Sekundäre und tertiäre amine als reibungsmodifikatoren für automatikgetriebeflüssigkeiten
US4960530A (en) Lubricating oil composition
CA2155063C (en) Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
WO1989006683A1 (en) Mixtures of partial fatty acid esters of polyhydric alcohols and sulfurized compositions, and use as lubricant additives
EP1534805A1 (de) Reibungsmodifikatoren für verbesserte antirubbelleistung und hohe statische reibung in kraftübertragungsfluiden
US3833496A (en) Oil composition
EP0712923A1 (de) Thiocarbamate und Phosphorester enthaltende Schmiermittel und Flüssigkeiten
EP0537338B1 (de) Thermisch stabile Zusammensetzungen und diese enthaltende Schmiermitteln und funktionelle Flüssigkeiten
EP0562062B1 (de) Abdichtungen aus fluorkohlenstoff schützende zusätze für schmieröle
JPH093471A (ja) チオリン含有エステルまたはそれらとオキシアルキレン基との塩を含有する潤滑組成物、機能流体およびグリース、ならびにそれらの使用方法
EP0335701A2 (de) Schmierölzusammensetzung
US5028345A (en) Lubricating oil composition
US4960528A (en) Lubricating oil composition
AU608318B2 (en) Sulphur-containing borate esters
US5362409A (en) Grease compositions
EP0556404A1 (de) Schmierölzusammensetzung
JPH04342794A (ja) 潤滑油組成物および濃厚物およびそれらの使用
US5124055A (en) Lubricating oil composition
CA1224470A (en) Succinimide complexes of borated fatty acid esters of glycerol and lubricating compositions containing same
US5154844A (en) Lubricant additives and their production

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

17P Request for examination filed

Effective date: 19900402

17Q First examination report despatched

Effective date: 19910128

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19910608