US20080015127A1 - Boundary friction reducing lubricating composition - Google Patents
Boundary friction reducing lubricating composition Download PDFInfo
- Publication number
- US20080015127A1 US20080015127A1 US11/457,579 US45757906A US2008015127A1 US 20080015127 A1 US20080015127 A1 US 20080015127A1 US 45757906 A US45757906 A US 45757906A US 2008015127 A1 US2008015127 A1 US 2008015127A1
- Authority
- US
- United States
- Prior art keywords
- dispersant
- composition
- containing compound
- molybdenum
- nitrogen
- 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.)
- Abandoned
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
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
- C10M141/08—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 sulfur-, selenium- or tellurium-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
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts 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
- 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
- C10M2215/28—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
- C10M2217/043—Mannich bases
-
- 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
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
-
- 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
- C10N2010/08—Groups 4 or 14
-
- 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
- C10N2010/12—Groups 6 or 16
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
-
- 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
- C10N2030/02—Pour-point; Viscosity index
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2030/44—Boron free or low content boron 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
- C10N2030/54—Fuel economy
-
- 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
- C10N2030/56—Boundary lubrication or thin film lubrication
-
- 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
Definitions
- the present disclosure relates to a lubricating composition
- a lubricating composition comprising a base oil, a friction modifier, and a dispersant, wherein the lubricating composition comprises less than about 325 ppm of boron.
- a lubricant composition that is inexpensive and can provide at least one of reduced boundary friction and increased fuel economy.
- a lubricating composition comprising a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- a method of formulating a lubricating composition having improved fuel efficiency comprising providing a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- a method of reducing boundary friction on a surface comprising providing to the surface a lubricating composition comprising a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- the present disclosure relates to a lubricating composition
- a lubricating composition comprising a base oil, a friction modifier, and a dispersant, wherein the lubricating composition comprises less than about 325 ppm of boron.
- the dispersant for use in the disclosed lubricating composition can be selected from any of the ashless dispersants known to those skilled in the art. Suitable ashless dispersants may include ashless dispersants such as succinimide dispersants, Mannich base dispersants, and polymeric polyamine dispersants. In an aspect, the dispersant comprises a basic nitrogen. In another aspect, the dispersant is a non-boron-containing dispersant. Hydrocarbyl-substituted succinic acylating agents can be used to make hydrocarbyl-substituted succinimides.
- the hydrocarbyl-substituted succinic acylating agents include, but are not limited to, hydrocarbyl-substituted succinic acids, hydrocarbyl-substituted succinic anhydrides, the hydrocarbyl-substituted succinic acid halides (for example, the acid fluorides and acid chlorides), and the esters of the hydrocarbyl-substituted succinic acids and lower alcohols (e.g., those containing up to 7 carbon atoms), that is, hydrocarbyl-substituted compounds which can function as carboxylic acylating agents.
- hydrocarbyl-substituted succinic acids include, but are not limited to, hydrocarbyl-substituted succinic acids, hydrocarbyl-substituted succinic anhydrides, the hydrocarbyl-substituted succinic acid halides (for example, the acid fluorides and acid chlorides), and the esters of the hydro
- Hydrocarbyl substituted acylating agents can be made by reacting a polyolefin or chlorinated polyolefin of appropriate molecular weight with maleic anhydride. Similar carboxylic reactants can be used to make the acylating agents. Such reactants can include, but are not limited to, maleic acid, fumaric acid, malic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, ethylmaleic anhydride, dimethylmaleic anhydride, ethylmaleic acid, dimethylmaleic acid, hexylmaleic acid, and the like, including the corresponding acid halides and lower aliphatic esters.
- the molecular weight of the olefin can vary depending upon the intended use of the substituted succinic anhydrides.
- the substituted succinic anhydrides can have a hydrocarbyl group of from about 8-500 carbon atoms.
- substituted succinic anhydrides used to make lubricating oil dispersants can typically have a hydrocarbyl group of about 40-500 carbon atoms.
- Mn number average molecular weight
- the olefins used to make these substituted succinic anhydrides can include a mixture of different molecular weight components resulting from the polymerization of low molecular weight olefin monomers such as ethylene, propylene and isobutylene.
- the mole ratio of maleic anhydride to olefin can vary widely. It can vary, for example, from about 5:1 to about 1:5, or for example, from about 1:1 to about 3:1.
- olefins such as polyisobutylene having a number average molecular weight of about 500 to about 7000, or as a further example, about 800 to about 3000 or higher and the ethylene-alpha-olefin copolymers
- the maleic anhydride can be used in stoichiometric excess, e.g. 1.1 to 3 moles maleic anhydride per mole of olefin.
- the unreacted maleic anhydride can be vaporized from the resultant reaction mixture.
- Polyalkenyl succinic anhydrides can be converted to polyalkyl succinic anhydrides by using conventional reducing conditions such as catalytic hydrogenation.
- a suitable catalyst is palladium on carbon.
- polyalkenyl succinimides can be converted to polyalkyl succinimides using similar reducing conditions.
- the polyalkyl or polyalkenyl substituent on the succinic anhydrides employed herein can be generally derived from polyolefins which are polymers or copolymers of mono-olefins, particularly 1-mono-olefins, such as ethylene, propylene and butylene.
- the mono-olefin employed can have about 2 to about 24 carbon atoms, or as a further example, about 3 to about 12 carbon atoms.
- Other suitable mono-olefins include propylene, butylene, particularly isobutylene, 1-octene and 1-decene.
- Polyolefins prepared from such mono-olefins include polypropylene, polybutene, polyisobutene, and the polyalphaolefins produced from 1-octene and 1-decene.
- the dispersant is a polyisobutylene-based dispersant.
- the ashless dispersant can include one or more alkenyl succinimides of an amine having at least one primary amino group capable of forming an imide group.
- the alkenyl succinimides can be formed by conventional methods such as by heating an alkenyl succinic anhydride, acid, acid-ester, acid halide, or lower alkyl ester with an amine containing at least one primary amino group.
- the alkenyl succinic anhydride can be made readily by heating a mixture of polyolefin and maleic anhydride to about 180°-220° C.
- the polyolefin can be a polymer or copolymer of a lower monoolefin such as ethylene, propylene, isobutene and the like, having a number average molecular weight in the range of about 300 to about 3000 as determined by gel permeation chromatography (GPC).
- GPC gel permeation chromatography
- Amines which can be employed in forming the ashless dispersant include any that have at least one primary amino group which can react to form an imide group and at least one additional primary or secondary amino group and/or at least one hydroxyl group.
- a few representative examples are: N-methyl-propanediamine, N-dodecylpropanediamine, N-aminopropyl-piperazine, ethanolamine, N-ethanol-ethylenediamine, and the like.
- Suitable amines can include alkylene polyamines, such as propylene diamine, dipropylene triamine, di-(1,2-butylene)triamine, and tetra-(1,2-propylene)pentamine.
- alkylene polyamines such as propylene diamine, dipropylene triamine, di-(1,2-butylene)triamine, and tetra-(1,2-propylene)pentamine.
- a further example includes the ethylene polyamines which can be depicted by the formula H 2 N(CH 2 CH 2 -NH) n H, wherein n can be an integer from about one to about ten. These include: ethylene diamine, diethylene triamine (DETA), triethylene tetramine (TETA), tetraethylene pentamine (TEPA), pentaethylene hexamine (PEHA), and the like, including mixtures thereof in which case n is the average value of the mixture.
- DETA diethylene triamine
- TETA triethylene tetra
- Such ethylene polyamines have a primary amine group at each end so they can form mono-alkenylsuccinimides and bis-alkenylsuccinimides.
- Commercially available ethylene polyamine mixtures can contain minor amounts of branched species and cyclic species such as N-aminoethyl piperazine, N,N′-bis(aminoethyl)piperazine, N,N′-bis(piperazinyl)ethane, and like compounds.
- the commercial mixtures can have approximate overall compositions falling in the range corresponding to diethylene triamine to tetraethylene pentamine.
- the molar ratio of polyalkenyl succinic anhydride to polyalkylene polyamines can be from about 1:1 to about 3.0:1.
- the dispersant can include the products of the reaction of a polyethylene polyamine, e.g. triethylene tetramine or tetraethylene pentamine, with a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, such as polyisobutene, of suitable molecular weight, with an unsaturated polycarboxylic acid or anhydride, e.g., maleic anhydride, maleic acid, fumaric acid, or the like, including mixtures of two or more such substances.
- a polyethylene polyamine e.g. triethylene tetramine or tetraethylene pentamine
- a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, such as polyisobutene, of suitable molecular weight
- an unsaturated polycarboxylic acid or anhydride e.g., maleic anhydride, maleic acid, fumaric acid, or the like, including mixtures of two or
- Polyamines that are also suitable in preparing the dispersants described herein include N-arylphenylenediamines, such as N-phenylphenylenediamines, for example, N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, and N-phenyl-1,2-phenylenediamine; aminothiazoles such as aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole; aminocarbazoles; aminoindoles; aminopyrroles; amino-indazolinones; aminomercaptotriazoles; aminoperimidines; aminoalkyl imidazoles, such as 1-(2-aminoethyl)imidazol- e, 1-(3-aminopropyl)imidazole; and aminoalkyl morpholines, such as 4-(3-aminopropyl)morpholine. These polyamines are described in more detail in
- Additional polyamines useful in forming the hydrocarbyl-substituted succinimides include polyamines having at least one primary or secondary amino group and at least one tertiary amino group in the molecule as taught in U.S. Pat. Nos. 5,634,951 and 5,725,612, the disclosures of which are hereby incorporated by reference herein.
- Non-limiting examples of suitable polyamines include N,N,N′′,N′′-tetraalkyldialkylenetriamines (two terminal tertiary amino groups and one central secondary amino group), N,N,N′,N′′-tetraalkyltrialkylenetetramines (one terminal tertiary amino group, two internal tertiary amino groups and one terminal primary amino group), N,N,N′,N′′,N′′′-pentaalkyltrialkylenetetramines (one terminal tertiary amino group, two internal tertiary amino groups and one terminal secondary amino group), tris(dialkylaminoalkyl)aminoalkylmethanes (three terminal tertiary amino groups and one terminal primary amino group), and like compounds, wherein the alkyl groups are the same or different and typically contain no more than about 12 carbon atoms each, and which can contain from about 1 to about 4 carbon atoms each. As a further example, these alkyl groups can
- Hydroxyamines suitable for herein include compounds, oligomers or polymers containing at least one primary or secondary amine capable of reacting with the hydrocarbyl-substituted succinic acid or anhydride.
- hydroxyamines suitable for use herein include aminoethylethanolamine (AEEA), aminopropyldiethanolamine (APDEA), ethanolamine, diethanolamine (DEA), partially propoxylated hexamethylene diamine (for example HMDA-2PO or HMDA-3PO), 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.
- the mole ratio of amine to hydrocarbyl-substituted succinic acid or anhydride can range from about 1:1 to about 3.0:1.
- Another example of a mole ratio of amine to hydrocarbyl-substituted succinic acid or anhydride may range from about 1.5:1 to about 2.0:1.
- the foregoing dispersant can also be a post-treated dispersant made, for example, by treating the dispersant with maleic anhydride and boric acid as described, for example, in U.S. Pat. No. 5,789,353, or by treating the dispersant with nonylphenol, formaldehyde and glycolic acid as described, for example, in U.S. Pat. No. 5,137,980, the disclosures of which are hereby incorporated y reference in their entirety.
- the Mannich base dispersants can be a reaction product of an alkyl phenol, typically having a long chain alkyl substituent on the ring, with one or more aliphatic aldehydes containing from about 1 to about 7 carbon atoms (for example, formaldehyde and derivatives thereof), and polyamines (especially polyalkylene polyamines).
- a Mannich base ashless dispersants can be formed by condensing about one molar proportion of long chain hydrocarbon-substituted phenol with from about 1 to about 2.5 moles of formaldehyde and from about 0.5 to about 2 moles of polyalkylene polyamine.
- Hydrocarbon sources for preparation of the Mannich polyamine dispersants can be those derived from substantially saturated petroleum fractions and olefin polymers, such as polymers of mono-olefins having from 2 to about 6 carbon atoms.
- the hydrocarbon source generally contains, for example, at least about 40 carbon atoms, and as a further example, at least about 50 carbon atoms to provide substantial oil solubility to the dispersant.
- the olefin polymers having a GPC number average molecular weight range from about 600 to 5,000 can be suitable. However, polymers of higher molecular weight can also be used.
- Suitable hydrocarbon sources can be isobutylene polymers and polymers made from a mixture of isobutene and a raffinate stream.
- Suitable Mannich base dispersants can be Mannich base ashless dispersants formed by condensing about one molar proportion of long chain hydrocarbon-substituted phenol with from about 1 to about 2.5 moles of formaldehyde and from about 0.5 to about 2 moles of polyalkylene polyamine.
- Polymeric polyamine dispersants suitable as the ashless dispersants are polymers containing basic amine groups and oil solubilizing groups (for example, pendant alkyl groups having at least about 8 carbon atoms). Such materials are illustrated by interpolymers formed from various monomers such as decyl methacrylate, vinyl decyl ether or relatively high molecular weight olefins, with aminoalkyl acrylates and aminoalkyl acrylamides. Examples of polymeric polyamine dispersants are set forth in U.S. Pat. Nos.
- Polymeric polyamines can include hydrocarbyl polyamines wherein the hydrocarbyl group is composed of the polymerization product of isobutene and a raffinate I stream as described above.
- PIB-amine and PIB-polyamines can also be used.
- Borated dispersants can be formed by boronating (“borating”) an ashless dispersant having basic nitrogen and/or at least one hydroxyl group in the molecule, such as a succinimide dispersant, succinamide dispersant, succinic ester dispersant, succinic ester-amide dispersant, Mannich base dispersant, or hydrocarbyl amine or polyamine dispersant.
- boronating an ashless dispersant having basic nitrogen and/or at least one hydroxyl group in the molecule, such as a succinimide dispersant, succinamide dispersant, succinic ester dispersant, succinic ester-amide dispersant, Mannich base dispersant, or hydrocarbyl amine or polyamine dispersant.
- the borated dispersant can include a high molecular weight dispersant treated with boron such that the borated dispersant includes up to about 2 wt % of boron, for example from about 0.8 wt % or less of boron, as a further example from about 0.1 to about 0.7 wt % of boron, as an even further example, from about 0.25 to about 0.7 wt % of boron, and as a further example from about 0.35 to about 0.7 wt % of boron.
- the dispersant can be dissolved in oil of suitable viscosity for ease of handling. It should be understood that the weight percentages given here are for neat dispersant, without any diluent oil added.
- a dispersant can be further reacted with an organic acid, an anhydride, and/or an aldehyde/phenol mixture. Such a process can enhance compatibility with elastomer seals, for example.
- the borated dispersant can further include a mixture of borated dispersants.
- the borated dispersant can include a nitrogen-containing dispersant and/or may be free of phosphorus.
- a dispersant can be present in the lubricating composition in an amount of about 0.1 wt % to about 10 wt %, for example from about 2 wt % to about 7 wt %, and as a further example from about 3 wt % to about 5 wt % of the lubricating composition.
- the friction modifier for use in the disclosed lubricating composition can be selected from among many suitable compounds and materials useful for imparting this function in lubricant compositions.
- the friction modifier can be used as a single type of compound or a mixture of different types of compounds.
- Non-limiting examples of the friction modifier include a nitrogen-containing compound, an ash-containing compound, and a non-nitrogen-containing compound.
- the disclosed lubricating compositions can comprise a non-nitrogen-containing compound and a molybdenum-containing compound.
- the nitrogen-containing compound can be any compound that comprises a basic nitrogen.
- the nitrogen-containing compound can be a long chain alkylene amine.
- Long chain alkylene amine friction modifying compounds include, for example, N-aliphatic hydrocarbyl-substituted trimethylenediamines in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms.
- a non-limiting example of such friction modifier compounds is N-oleyl-trimethylene diamine.
- Other suitable compounds include N-tallow-trimethylene diamine and N-coco-trimethylene diamine.
- One group of friction modifiers includes the N-aliphatic hydrocarbyl-substituted diethanol amines in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms.
- hydrocarbyl substituent or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character.
- hydrocarbyl groups include:
- hydrocarbon substituents that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form an alicyclic radical);
- aliphatic e.g., alkyl or alkenyl
- alicyclic e.g., cycloalkyl, cycloalkenyl
- aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form an alicyclic radical);
- substituted hydrocarbon substituents that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
- hetero substituents that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms.
- Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents as pyridyl, furyl, thienyl and imidazolyl.
- no more than two, for example no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; typically, there will be no non-hydrocarbon substituents in the hydrocarbyl group.
- the friction modifier can comprise a mixture of different compounds, such as a combination of at least one N-aliphatic hydrocarbyl-substituted diethanol amine and at least one N-aliphatic hydrocarbyl-substituted trimethylene diamine in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms.
- Further details concerning this friction modifier combination are set forth in U.S. Pat. Nos. 5,372,735 and 5,441,656, the disclosures of which are hereby incorporated by reference.
- the friction modifier can be an ash-containing compound.
- the ash-containing compound can be a molybdenum-containing compound.
- the molybdenum-containing compound for use in the lubricating compositions disclosed herein can be sulfur- and/or phosphorus-free.
- a sulfur- and phosphorus-free molybdenum-containing compound can be prepared by reacting a sulfur and phosphorus-free molybdenum source with an organic compound containing amino and/or alcohol groups. Examples of sulfur- and phosphorus-free molybdenum sources include molybdenum trioxide, ammonium molybdate, sodium molybdate and potassium molybdate.
- the amino groups can be monoamines, diamines, or polyamines.
- the alcohol groups can be mono-substituted alcohols, diols or bis-alcohols, or polyalcohols.
- the reaction of diamines with fatty oils produces a product containing both amino and alcohol groups that can react with the sulfur- and phosphorus-free molybdenum source.
- Examples of sulfur- and phosphorus-free molybdenum-containing compounds appearing in patents and patent applications which are fully incorporated herein by reference include the following: Compounds prepared by reacting certain basic nitrogen compounds with a molybdenum source as defined in U.S. Pat. Nos. 4,259,195 and 4,261,843. Compounds prepared by reacting a hydrocarbyl substituted hydroxy alkylated amine with a molybdenum source as defined in U.S. Pat. No. 4,164,473. Compounds prepared by reacting a phenol aldehyde condensation product, a mono-alkylated alkylene diamine, and a molybdenum source as defined in U.S. Pat. No. 4,266,945.
- a sulfur-containing, molybdenum-containing compound can also be used in the lubricating compositions disclosed herein.
- the sulfur-containing, molybdenum-containing compound can be prepared by a variety of methods. One method involves reacting a sulfur- and/or phosphorus-free molybdenum source with an amino group and one or more sulfur sources.
- Sulfur sources can include for example, but are not limited to, carbon disulfide, hydrogen sulfide, sodium sulfide and elemental sulfur.
- the sulfur-containing, molybdenum-containing compound can be prepared by reacting a sulfur-containing molybdenum source with an amino group or thiuram group and optionally a second sulfur source.
- the reaction of molybdenum trioxide with a secondary amine and carbon disulfide produces molybdenum dithiocarbanates.
- the reaction of (NH 4 ) 2 Mo 3 S 13 *n(H 2 O) where n ranges from about 0 to 2, with a tetralkylthiuram disulfide produces a trinuclear sulfur-containing molybdenum dithiocarbamate.
- Non-limiting examples of sulfur-containing, molybdenum-containing compounds appearing in patents and patent applications include the following: Compounds prepared by reacting molybdenum trioxide with a secondary amine and carbon disulfide as defined in U.S. Pat. Nos. 3,509,051 and 3,356,702. Compounds prepared by reacting a sulfur-free molybdenum source with a secondary amine, carbon disulfide, and an additional sulfur source as defined in U.S. Pat. No. 4,098,705. Compounds prepared by reacting a molybdenum halide with a secondary amine and carbon disulfide as defined in U.S. Pat. No. 4,178,258.
- molybdenum-containing compounds include molybdenum carboxylates, molybdenum amides, molybdenum thiophosphates, molybdenum thiocarbamates, molybdenum dithiocarbamates, and so forth.
- ash-containing compounds include, but are not limited to, titanium-containing compounds and tungsten-containing compounds.
- Another suitable group of friction modifiers include non-nitrogen-containing compounds, such as polyolesters, for example, glycerol monooleate (GMO), glycerol monolaurate (GML), and the like.
- GMO glycerol monooleate
- GML glycerol monolaurate
- the friction modifying compound can be present in the lubricating composition in any desired or effective amount.
- the lubricating composition can comprise from about 0.05% to about 3% by weight, for example from about 0.2% to about 1.5%, and as a further example from about 0.3% to about 1% by weight relative to the total weight of the lubricating composition.
- any amount can be used.
- the lubricating composition disclosed herein can comprise a base oil.
- Base oils suitable for use in formulating the disclosed compositions can be selected from any of the synthetic or mineral oils or mixtures thereof.
- Mineral oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as other mineral lubricating oils such as liquid petroleum oils and solvent treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types. Oils derived from coal or shale are also suitable. Further, oils derived from a gas-to-liquid process are also suitable.
- the base oil can be present in a major amount, wherein “major amount” is understood to mean greater than or equal to 50%, for example from about 80 to about 98 percent by weight of the lubricant composition.
- the base oil typically has a viscosity of, for example, from about 2 to about 15 cSt and, as a further example, from about 2 to about 10 cSt at 100° C.
- Non-limiting examples of synthetic oils include hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, etc.); polyalphaolefins such as poly(1-hexenes), poly-(1-octenes), poly(1-decenes), etc.
- hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, etc.); polyalphaolefins such as poly(1-hexenes), poly-(1-octenes), poly(1-decenes), etc.
- alkylbenzenes e.g., dodecylbenzenes, tetradecylbenzenes, di-nonylbenzenes, di-(2-ethylhexyl)benzenes, etc.
- polyphenyls e.g., biphenyls, terphenyl, alkylated polyphenyls, etc.
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc. constitute another class of known synthetic oils that can be used.
- Such oils are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether having an average molecular weight of about 1000, diphenyl ether of polyethylene glycol having a molecular weight of about 500-1000, diethyl ether of polypropylene glycol having a molecular weight of about 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C 3-8 fatty acid esters, or the C 13 Oxo acid diester of tetraethylene glycol.
- esters of dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, etc.
- alcohols e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.
- these esters include dibutyl adipate, di(2-ethylhexyl)sebacate, di-n-hexyl fumarate, dioctyl sebacate, diusooctyl azelate, diisodecy
- Esters useful as synthetic oils also include those made from C 5-12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylol propane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
- the base oil used which can be used to make the compositions as described herein can be selected from any of the base oils in Groups I-V as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
- Such base oil groups are as follows:
- Group I contain less than 90% saturates and/or greater than 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120;
- Group II contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120;
- Group III contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 120;
- Group IV are polyalphaolefins (PAO); and
- Group V include all other basestocks not included in Group I, II, III or IV.
- test methods used in defining the above groups are ASTM D2007 for saturates; ASTM D2270 for viscosity index; and one of ASTM D2622, 4294, 4927 and 3120 for sulfur.
- Group IV basestocks i.e. polyalphaolefins (PAO) include hydrogenated oligomers of an alpha-olefin, the most important methods of oligomerisation being free radical processes, Ziegler catalysis, and cationic, Friedel-Crafts catalysis.
- PAO polyalphaolefins
- the polyalphaolefins typically have viscosities in the range of 2 to 100 cSt at 100° C., for example 4 to 8 cSt at 100° C. They can, for example, be oligomers of branched or straight chain alpha-olefins having from about 2 to about 30 carbon atoms, non-limiting examples include polypropenes, polyisobutenes, poly-1-butenes, poly-1-hexenes, poly-1-octenes and poly-1-decene. Included are homopolymers, interpolymers and mixtures.
- a “Group I basestock” also includes a Group I basestock with which basestock(s) from one or more other groups can be admixed, provided that the resulting admixture has characteristics falling within those specified above for Group I basestocks.
- Exemplary basestocks include Group I basestocks and mixtures of Group II basestocks with Group I bright stock.
- Basestocks suitable for use herein can be made using a variety of different processes including but not limited to distillation, solvent refining, hydrogen processing, oligomerisation, esterification, and re-refining.
- the base oil can be an oil derived from Fischer-Tropsch synthesized hydrocarbons.
- Fischer-Tropsch synthesized hydrocarbons can be made from synthesis gas containing H 2 and CO using a Fischer-Tropsch catalyst.
- Such hydrocarbons typically require further processing in order to be useful as the base oil.
- the hydrocarbons can be hydroisomerized using processes disclosed in U.S. Pat. No. 6,103,099 or 6,180,575; hydrocracked and hydroisomerized using processes disclosed in U.S. Pat. No. 4,943,672 or 6,096,940; dewaxed using processes disclosed in U.S. Pat. No. 5,882,505; or hydroisomerized and dewaxed using processes disclosed in U.S. Pat. No. 6,013,171; 6,080,301; or 6,165,949.
- Unrefined, refined and rerefined oils either mineral or synthetic (as well as mixtures of two or more of any of these) of the type disclosed hereinabove can be used in the base oils.
- Unrefined oils are those obtained directly from a mineral or synthetic source without further purification treatment.
- a shale oil obtained directly from retorting operations a petroleum oil obtained directly from primary distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
- Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed to removal of spent additives, contaminants, and oil breakdown products.
- the lubricating composition can comprise less than about 325 ppm of boron. In a further aspect, the lubricating composition can comprise less than about 300 ppm of boron, and for example less than 280 ppm of boron.
- the disclosed lubricating composition can reduce boundary friction on a surface of a machine as compared to a surface that is not lubricated with the disclosed lubricating composition.
- the lubricating composition can be applied/provided to any surface of any machine, such as for example an engine, a gear, etc.
- other components can be present in the lubricant composition.
- Non-limiting examples of other components include antiwear agents, dispersants, diluents, defoamers, demulsifiers, anti-foam agents, corrosion inhibitors, extreme pressure agents, seal well agents, antioxidants, pour point depressants, rust inhibitors and friction modifiers.
- Dispersant A High vinylidene PIB based dispersant with TEPA as the amine and is boronated.
- Typical Analytical % N 1.1; TBN 16.6 mgKOH/g; % B 1.12 Dispersant B Conventional PIB based dispersant with with TEPA as the amine.
- Typical Analytical % N 1.2; TBN 16.6 mgKOH/g Dispersant C High vinylidene PIB based dispersant with E-100 as the amine and is boronated.
- the Comparative Example 2 illustrated that a non-nitrogen-containing compound reduced boundary friction by 27% as compared to Comparative Example 1, which did not contain a friction modifier.
- the combination of a non-nitrogen-containing compound and a non-boron-containing dispersant (Invention 2) reduced boundary friction by 46% as compared to Comparative Example 1.
- mixtures of a boron-containing and a non-boron-containing compound with a non-nitrogen-containing compound (Inventions 3 and 4) produced lower boundary friction coefficients as compared to Comparative Example 2.
- Comparative Examples 3 and 4 illustrated that a molybdenum-containing compound and a boron-containing dispersant reduced boundary friction by 26% and 30%, respectively, as compared to the boron-containing dispersant alone (Comparative Example 1). However, the combination of a molybdenum-containing compound and a non-boron-containing dispersant (Inventions 5 and 6) reduced boundary friction by 36% and 61%, respectively.
- Comparative Example 5 illustrated that a combination of a boron-containing dispersant, a non-nitrogen-containing compound, and a molybdenum-containing compound reduced boundary friction by 22%, as compared to Comparative Example 1.
- Invention 7 illustrated that a combination of a non-boron-containing dispersant, a non-nitrogen-containing compound, and a molybdenum-containing compound reduced boundary friction by 37%, as compared to Comparative Example 1.
Abstract
Description
- 1. Field of the Disclosure
- The present disclosure relates to a lubricating composition comprising a base oil, a friction modifier, and a dispersant, wherein the lubricating composition comprises less than about 325 ppm of boron.
- 1. Background of the Disclosure
- In recent years, there has been growing concern to produce energy-efficient lubricated components. Moreover, modern engine oil specifications require lubricants to demonstrate fuel efficiency in standardized engine tests. The thickness and frictional characteristics of lubricant films are known to affect the fuel economy properties of oils.
- When rubbing surfaces in a machine (engine, gear system or transmission) come in contact a frictional force exists that retards the motion of the surfaces. This frictional force, called boundary friction, reduces the efficiency of the machine.
- It is known that non-nitrogen-containing and molybdenum-containing friction modifiers reduce boundary friction. See SAE 2000-01-1972. Moreover, it is known that friction is lower with the combination of molybdenum-containing friction modifiers and ethylene-propylene polymeric dispersants than when the same friction modifiers are combined with other dispersants, such as Mannich or succinimides. See U.S. Pat. No. 6,528,461.
- What is needed is a lubricant composition that is inexpensive and can provide at least one of reduced boundary friction and increased fuel economy.
- In accordance with the disclosure, there is disclosed a lubricating composition comprising a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- In an aspect, there is also disclosed a method of formulating a lubricating composition having improved fuel efficiency comprising providing a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- In a further aspect, there is disclosed a method of reducing boundary friction on a surface comprising providing to the surface a lubricating composition comprising a base oil, a dispersant, and a friction modifier, wherein the composition comprises less than about 325 ppm of boron.
- Additional objects and advantages of the invention will be set forth in part in the description which follows, or may be learned by practice of the disclosure. The objects and advantages of the disclosure will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims.
- It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention, as claimed.
- The present disclosure relates to a lubricating composition comprising a base oil, a friction modifier, and a dispersant, wherein the lubricating composition comprises less than about 325 ppm of boron.
- The dispersant for use in the disclosed lubricating composition can be selected from any of the ashless dispersants known to those skilled in the art. Suitable ashless dispersants may include ashless dispersants such as succinimide dispersants, Mannich base dispersants, and polymeric polyamine dispersants. In an aspect, the dispersant comprises a basic nitrogen. In another aspect, the dispersant is a non-boron-containing dispersant. Hydrocarbyl-substituted succinic acylating agents can be used to make hydrocarbyl-substituted succinimides. The hydrocarbyl-substituted succinic acylating agents include, but are not limited to, hydrocarbyl-substituted succinic acids, hydrocarbyl-substituted succinic anhydrides, the hydrocarbyl-substituted succinic acid halides (for example, the acid fluorides and acid chlorides), and the esters of the hydrocarbyl-substituted succinic acids and lower alcohols (e.g., those containing up to 7 carbon atoms), that is, hydrocarbyl-substituted compounds which can function as carboxylic acylating agents.
- Hydrocarbyl substituted acylating agents can be made by reacting a polyolefin or chlorinated polyolefin of appropriate molecular weight with maleic anhydride. Similar carboxylic reactants can be used to make the acylating agents. Such reactants can include, but are not limited to, maleic acid, fumaric acid, malic acid, tartaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid, ethylmaleic anhydride, dimethylmaleic anhydride, ethylmaleic acid, dimethylmaleic acid, hexylmaleic acid, and the like, including the corresponding acid halides and lower aliphatic esters.
- The molecular weight of the olefin can vary depending upon the intended use of the substituted succinic anhydrides. Typically, the substituted succinic anhydrides can have a hydrocarbyl group of from about 8-500 carbon atoms. However, substituted succinic anhydrides used to make lubricating oil dispersants can typically have a hydrocarbyl group of about 40-500 carbon atoms. With high molecular weight substituted succinic anhydrides, it is more accurate to refer to number average molecular weight (Mn) since the olefins used to make these substituted succinic anhydrides can include a mixture of different molecular weight components resulting from the polymerization of low molecular weight olefin monomers such as ethylene, propylene and isobutylene.
- The mole ratio of maleic anhydride to olefin can vary widely. It can vary, for example, from about 5:1 to about 1:5, or for example, from about 1:1 to about 3:1. With olefins such as polyisobutylene having a number average molecular weight of about 500 to about 7000, or as a further example, about 800 to about 3000 or higher and the ethylene-alpha-olefin copolymers, the maleic anhydride can be used in stoichiometric excess, e.g. 1.1 to 3 moles maleic anhydride per mole of olefin. The unreacted maleic anhydride can be vaporized from the resultant reaction mixture.
- Polyalkenyl succinic anhydrides can be converted to polyalkyl succinic anhydrides by using conventional reducing conditions such as catalytic hydrogenation. For catalytic hydrogenation, a suitable catalyst is palladium on carbon. Likewise, polyalkenyl succinimides can be converted to polyalkyl succinimides using similar reducing conditions.
- The polyalkyl or polyalkenyl substituent on the succinic anhydrides employed herein can be generally derived from polyolefins which are polymers or copolymers of mono-olefins, particularly 1-mono-olefins, such as ethylene, propylene and butylene. The mono-olefin employed can have about 2 to about 24 carbon atoms, or as a further example, about 3 to about 12 carbon atoms. Other suitable mono-olefins include propylene, butylene, particularly isobutylene, 1-octene and 1-decene. Polyolefins prepared from such mono-olefins include polypropylene, polybutene, polyisobutene, and the polyalphaolefins produced from 1-octene and 1-decene. In an aspect, the dispersant is a polyisobutylene-based dispersant.
- In some aspects, the ashless dispersant can include one or more alkenyl succinimides of an amine having at least one primary amino group capable of forming an imide group. The alkenyl succinimides can be formed by conventional methods such as by heating an alkenyl succinic anhydride, acid, acid-ester, acid halide, or lower alkyl ester with an amine containing at least one primary amino group. The alkenyl succinic anhydride can be made readily by heating a mixture of polyolefin and maleic anhydride to about 180°-220° C. The polyolefin can be a polymer or copolymer of a lower monoolefin such as ethylene, propylene, isobutene and the like, having a number average molecular weight in the range of about 300 to about 3000 as determined by gel permeation chromatography (GPC).
- Amines which can be employed in forming the ashless dispersant include any that have at least one primary amino group which can react to form an imide group and at least one additional primary or secondary amino group and/or at least one hydroxyl group. A few representative examples are: N-methyl-propanediamine, N-dodecylpropanediamine, N-aminopropyl-piperazine, ethanolamine, N-ethanol-ethylenediamine, and the like.
- Suitable amines can include alkylene polyamines, such as propylene diamine, dipropylene triamine, di-(1,2-butylene)triamine, and tetra-(1,2-propylene)pentamine. A further example includes the ethylene polyamines which can be depicted by the formula H2N(CH2CH2-NH)nH, wherein n can be an integer from about one to about ten. These include: ethylene diamine, diethylene triamine (DETA), triethylene tetramine (TETA), tetraethylene pentamine (TEPA), pentaethylene hexamine (PEHA), and the like, including mixtures thereof in which case n is the average value of the mixture. Such ethylene polyamines have a primary amine group at each end so they can form mono-alkenylsuccinimides and bis-alkenylsuccinimides. Commercially available ethylene polyamine mixtures can contain minor amounts of branched species and cyclic species such as N-aminoethyl piperazine, N,N′-bis(aminoethyl)piperazine, N,N′-bis(piperazinyl)ethane, and like compounds. The commercial mixtures can have approximate overall compositions falling in the range corresponding to diethylene triamine to tetraethylene pentamine. The molar ratio of polyalkenyl succinic anhydride to polyalkylene polyamines can be from about 1:1 to about 3.0:1.
- In some aspects, the dispersant can include the products of the reaction of a polyethylene polyamine, e.g. triethylene tetramine or tetraethylene pentamine, with a hydrocarbon substituted carboxylic acid or anhydride made by reaction of a polyolefin, such as polyisobutene, of suitable molecular weight, with an unsaturated polycarboxylic acid or anhydride, e.g., maleic anhydride, maleic acid, fumaric acid, or the like, including mixtures of two or more such substances.
- Polyamines that are also suitable in preparing the dispersants described herein include N-arylphenylenediamines, such as N-phenylphenylenediamines, for example, N-phenyl-1,4-phenylenediamine, N-phenyl-1,3-phenylendiamine, and N-phenyl-1,2-phenylenediamine; aminothiazoles such as aminothiazole, aminobenzothiazole, aminobenzothiadiazole and aminoalkylthiazole; aminocarbazoles; aminoindoles; aminopyrroles; amino-indazolinones; aminomercaptotriazoles; aminoperimidines; aminoalkyl imidazoles, such as 1-(2-aminoethyl)imidazol- e, 1-(3-aminopropyl)imidazole; and aminoalkyl morpholines, such as 4-(3-aminopropyl)morpholine. These polyamines are described in more detail in U.S. Pat. Nos. 4,863,623 and 5,075,383, the disclosures of which are hereby incorporated by reference herein.
- Additional polyamines useful in forming the hydrocarbyl-substituted succinimides include polyamines having at least one primary or secondary amino group and at least one tertiary amino group in the molecule as taught in U.S. Pat. Nos. 5,634,951 and 5,725,612, the disclosures of which are hereby incorporated by reference herein. Non-limiting examples of suitable polyamines include N,N,N″,N″-tetraalkyldialkylenetriamines (two terminal tertiary amino groups and one central secondary amino group), N,N,N′,N″-tetraalkyltrialkylenetetramines (one terminal tertiary amino group, two internal tertiary amino groups and one terminal primary amino group), N,N,N′,N″,N′″-pentaalkyltrialkylenetetramines (one terminal tertiary amino group, two internal tertiary amino groups and one terminal secondary amino group), tris(dialkylaminoalkyl)aminoalkylmethanes (three terminal tertiary amino groups and one terminal primary amino group), and like compounds, wherein the alkyl groups are the same or different and typically contain no more than about 12 carbon atoms each, and which can contain from about 1 to about 4 carbon atoms each. As a further example, these alkyl groups can be methyl and/or ethyl groups. Polyamine reactants of this type can include dimethylaminopropylamine (DMAPA) and N-methyl piperazine.
- Hydroxyamines suitable for herein include compounds, oligomers or polymers containing at least one primary or secondary amine capable of reacting with the hydrocarbyl-substituted succinic acid or anhydride. Examples of hydroxyamines suitable for use herein include aminoethylethanolamine (AEEA), aminopropyldiethanolamine (APDEA), ethanolamine, diethanolamine (DEA), partially propoxylated hexamethylene diamine (for example HMDA-2PO or HMDA-3PO), 3-amino-1,2-propanediol, tris(hydroxymethyl)aminomethane, and 2-amino-1,3-propanediol.
- The mole ratio of amine to hydrocarbyl-substituted succinic acid or anhydride can range from about 1:1 to about 3.0:1. Another example of a mole ratio of amine to hydrocarbyl-substituted succinic acid or anhydride may range from about 1.5:1 to about 2.0:1.
- The foregoing dispersant can also be a post-treated dispersant made, for example, by treating the dispersant with maleic anhydride and boric acid as described, for example, in U.S. Pat. No. 5,789,353, or by treating the dispersant with nonylphenol, formaldehyde and glycolic acid as described, for example, in U.S. Pat. No. 5,137,980, the disclosures of which are hereby incorporated y reference in their entirety.
- The Mannich base dispersants can be a reaction product of an alkyl phenol, typically having a long chain alkyl substituent on the ring, with one or more aliphatic aldehydes containing from about 1 to about 7 carbon atoms (for example, formaldehyde and derivatives thereof), and polyamines (especially polyalkylene polyamines). For example, a Mannich base ashless dispersants can be formed by condensing about one molar proportion of long chain hydrocarbon-substituted phenol with from about 1 to about 2.5 moles of formaldehyde and from about 0.5 to about 2 moles of polyalkylene polyamine.
- Hydrocarbon sources for preparation of the Mannich polyamine dispersants can be those derived from substantially saturated petroleum fractions and olefin polymers, such as polymers of mono-olefins having from 2 to about 6 carbon atoms. The hydrocarbon source generally contains, for example, at least about 40 carbon atoms, and as a further example, at least about 50 carbon atoms to provide substantial oil solubility to the dispersant. The olefin polymers having a GPC number average molecular weight range from about 600 to 5,000 can be suitable. However, polymers of higher molecular weight can also be used. Suitable hydrocarbon sources can be isobutylene polymers and polymers made from a mixture of isobutene and a raffinate stream.
- Suitable Mannich base dispersants can be Mannich base ashless dispersants formed by condensing about one molar proportion of long chain hydrocarbon-substituted phenol with from about 1 to about 2.5 moles of formaldehyde and from about 0.5 to about 2 moles of polyalkylene polyamine.
- Polymeric polyamine dispersants suitable as the ashless dispersants are polymers containing basic amine groups and oil solubilizing groups (for example, pendant alkyl groups having at least about 8 carbon atoms). Such materials are illustrated by interpolymers formed from various monomers such as decyl methacrylate, vinyl decyl ether or relatively high molecular weight olefins, with aminoalkyl acrylates and aminoalkyl acrylamides. Examples of polymeric polyamine dispersants are set forth in U.S. Pat. Nos. 3,329,658; 3,449,250; 3,493,520; 3,519,565; 3,666,730; 3,687,849; and 3,702,300, the disclosures of which are hereby incorporated by reference in their entirety. Polymeric polyamines can include hydrocarbyl polyamines wherein the hydrocarbyl group is composed of the polymerization product of isobutene and a raffinate I stream as described above. PIB-amine and PIB-polyamines can also be used.
- Methods for the production of ashless dispersants as described above are known to those skilled in the art and are reported in the patent literature. For example, the synthesis of various ashless dispersants of the foregoing types is described in such patents as U.S. Pat. Nos. 2,459,112; 2,962,442, 2,984,550; 3,036,003; 3,163,603; 3,166,516; 3,172,892; 3,184,474; 3,202,678; 3,215,707; 3,216,936; 3,219,666; 3,236,770; 3,254,025; 3,271,310; 3,272,746; 3,275,554; 3,281,357; 3,306,908; 3,311,558; 3,316,177; 3,331,776; 3,340,281; 3,341,542; 3,346,493; 3,351,552; 3,355,270; 3,368,972; 3,381,022; 3,399,141; 3,413,347; 3,415,750; 3,433,744; 3,438,757; 3,442,808; 3,444,170; 3,448,047; 3,448,048; 3,448,049; 3,451,933; 3,454,497; 3,454,555; 3,454,607; 3,459,661; 3,461,172; 3,467,668; 3,493,520; 3,501,405; 3,522,179; 3,539,633; 3,541,012; 3,542,680; 3,543,678; 3,558,743; 3,565,804; 3,567,637; 3,574,101; 3,576,743; 3,586,629; 3,591,598; 3,600,372; 3,630,904; 3,632,510; 3,632,511; 3,634,515; 3,649,229; 3,697,428; 3,697,574; 3,703,536; 3,704,308; 3,725,277; 3,725,441; 3,725,480; 3,726,882; 3,736,357; 3,751,365; 3,756,953; 3,793,202; 3,798,165; 3,798,247; 3,803,039; 3,804,763; 3,836,471; 3,862,981; 3,872,019; 3,904,595; 3,936,480; 3,948,800; 3,950,341; 3,957,746; 3,957,854; 3,957,855; 3,980,569; 3,985,802; 3,991,098; 4,006,089; 4,011,380; 4,025,451; 4,058,468; 4,071,548; 4,083,699; 4,090,854; 4,173,540; 4,234,435; 4,354,950; 4,485,023; 5,137,980, and U.S. Pat. No. Re. 26,433, herein incorporated by reference.
- An example of a suitable ashless dispersant is a borated dispersant. Borated dispersants can be formed by boronating (“borating”) an ashless dispersant having basic nitrogen and/or at least one hydroxyl group in the molecule, such as a succinimide dispersant, succinamide dispersant, succinic ester dispersant, succinic ester-amide dispersant, Mannich base dispersant, or hydrocarbyl amine or polyamine dispersant. Methods that can be used for borating the various types of ashless dispersants described above are described in U.S. Pat. Nos. 3,087,936; 3,254,025; 3,281,428; 3,282,955; 2,284,409; 2,284,410; 3,338,832; 3,344,069; 3,533,945; 3,658,836; 3,703,536; 3,718,663; 4,455,243; and 4,652,387, the disclosures of which are hereby incorporated by reference in their entirety.
- The borated dispersant can include a high molecular weight dispersant treated with boron such that the borated dispersant includes up to about 2 wt % of boron, for example from about 0.8 wt % or less of boron, as a further example from about 0.1 to about 0.7 wt % of boron, as an even further example, from about 0.25 to about 0.7 wt % of boron, and as a further example from about 0.35 to about 0.7 wt % of boron. The dispersant can be dissolved in oil of suitable viscosity for ease of handling. It should be understood that the weight percentages given here are for neat dispersant, without any diluent oil added.
- A dispersant can be further reacted with an organic acid, an anhydride, and/or an aldehyde/phenol mixture. Such a process can enhance compatibility with elastomer seals, for example. The borated dispersant can further include a mixture of borated dispersants. As a further example, the borated dispersant can include a nitrogen-containing dispersant and/or may be free of phosphorus.
- A dispersant can be present in the lubricating composition in an amount of about 0.1 wt % to about 10 wt %, for example from about 2 wt % to about 7 wt %, and as a further example from about 3 wt % to about 5 wt % of the lubricating composition.
- The friction modifier for use in the disclosed lubricating composition can be selected from among many suitable compounds and materials useful for imparting this function in lubricant compositions. The friction modifier can be used as a single type of compound or a mixture of different types of compounds. Non-limiting examples of the friction modifier include a nitrogen-containing compound, an ash-containing compound, and a non-nitrogen-containing compound. In an aspect, the disclosed lubricating compositions can comprise a non-nitrogen-containing compound and a molybdenum-containing compound.
- The nitrogen-containing compound can be any compound that comprises a basic nitrogen. In an aspect, the nitrogen-containing compound can be a long chain alkylene amine. Long chain alkylene amine friction modifying compounds include, for example, N-aliphatic hydrocarbyl-substituted trimethylenediamines in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms. A non-limiting example of such friction modifier compounds is N-oleyl-trimethylene diamine. Other suitable compounds include N-tallow-trimethylene diamine and N-coco-trimethylene diamine.
- One group of friction modifiers includes the N-aliphatic hydrocarbyl-substituted diethanol amines in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms.
- As used herein, the term “hydrocarbyl substituent” or “hydrocarbyl group” is used in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. Examples of hydrocarbyl groups include:
- (1) hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form an alicyclic radical);
- (2) substituted hydrocarbon substituents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
- (3) hetero substituents, that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms. Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents as pyridyl, furyl, thienyl and imidazolyl. In general, no more than two, for example no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; typically, there will be no non-hydrocarbon substituents in the hydrocarbyl group.
- As discussed above, the friction modifier can comprise a mixture of different compounds, such as a combination of at least one N-aliphatic hydrocarbyl-substituted diethanol amine and at least one N-aliphatic hydrocarbyl-substituted trimethylene diamine in which the N-aliphatic hydrocarbyl-substituent is at least one straight chain aliphatic hydrocarbyl group free of acetylenic unsaturation and having in the range of about 14 to about 20 carbon atoms. Further details concerning this friction modifier combination are set forth in U.S. Pat. Nos. 5,372,735 and 5,441,656, the disclosures of which are hereby incorporated by reference.
- The friction modifier can be an ash-containing compound. In an aspect, the ash-containing compound can be a molybdenum-containing compound. The molybdenum-containing compound for use in the lubricating compositions disclosed herein can be sulfur- and/or phosphorus-free. A sulfur- and phosphorus-free molybdenum-containing compound can be prepared by reacting a sulfur and phosphorus-free molybdenum source with an organic compound containing amino and/or alcohol groups. Examples of sulfur- and phosphorus-free molybdenum sources include molybdenum trioxide, ammonium molybdate, sodium molybdate and potassium molybdate. The amino groups can be monoamines, diamines, or polyamines. The alcohol groups can be mono-substituted alcohols, diols or bis-alcohols, or polyalcohols. As an example, the reaction of diamines with fatty oils produces a product containing both amino and alcohol groups that can react with the sulfur- and phosphorus-free molybdenum source.
- Examples of sulfur- and phosphorus-free molybdenum-containing compounds appearing in patents and patent applications which are fully incorporated herein by reference include the following: Compounds prepared by reacting certain basic nitrogen compounds with a molybdenum source as defined in U.S. Pat. Nos. 4,259,195 and 4,261,843. Compounds prepared by reacting a hydrocarbyl substituted hydroxy alkylated amine with a molybdenum source as defined in U.S. Pat. No. 4,164,473. Compounds prepared by reacting a phenol aldehyde condensation product, a mono-alkylated alkylene diamine, and a molybdenum source as defined in U.S. Pat. No. 4,266,945. Compounds prepared by reacting a fatty oil, diethanolamine, and a molybdenum source as defined in U.S. Pat. No. 4,889,647. Compounds prepared by reacting a fatty oil or acid with 2-(2-aminoethyi)aminoethanol, and a molybdenum source as defined in U.S. Pat. No. 5,137,647. Compounds prepared by reacting a secondary amine with a molybdenum source as defined in U.S. Pat. No. 4,692,256. Compounds prepared by reacting a diol, diamino, or amino-alcohol compound with a molybdenum source as defined in U.S. Pat. No. 5,412,130. Compounds prepared by reacting a fatty oil, mono-alkylated alkylene diamine, and a molybdenum source as defined in European Patent Application EP 1 136 496 A1. Compounds prepared by reacting a fatty acid, mono-alkylated alkylene diamine, glycerides, and a molybdenum source as defined in European Patent Application EP 1 136 497 A1. Compounds prepared by reacting a fatty oil, diethanolamine, and a molybdenum source as defined in U.S. Pat. No. 4,889,647.
- In an aspect, a sulfur-containing, molybdenum-containing compound can also be used in the lubricating compositions disclosed herein. The sulfur-containing, molybdenum-containing compound can be prepared by a variety of methods. One method involves reacting a sulfur- and/or phosphorus-free molybdenum source with an amino group and one or more sulfur sources. Sulfur sources can include for example, but are not limited to, carbon disulfide, hydrogen sulfide, sodium sulfide and elemental sulfur. Alternatively, the sulfur-containing, molybdenum-containing compound can be prepared by reacting a sulfur-containing molybdenum source with an amino group or thiuram group and optionally a second sulfur source. As an example, the reaction of molybdenum trioxide with a secondary amine and carbon disulfide produces molybdenum dithiocarbanates. Alternatively, the reaction of (NH4)2Mo3S13*n(H2O) where n ranges from about 0 to 2, with a tetralkylthiuram disulfide, produces a trinuclear sulfur-containing molybdenum dithiocarbamate.
- Non-limiting examples of sulfur-containing, molybdenum-containing compounds appearing in patents and patent applications include the following: Compounds prepared by reacting molybdenum trioxide with a secondary amine and carbon disulfide as defined in U.S. Pat. Nos. 3,509,051 and 3,356,702. Compounds prepared by reacting a sulfur-free molybdenum source with a secondary amine, carbon disulfide, and an additional sulfur source as defined in U.S. Pat. No. 4,098,705. Compounds prepared by reacting a molybdenum halide with a secondary amine and carbon disulfide as defined in U.S. Pat. No. 4,178,258. Compounds prepared by reacting a molybdenum source with a basic nitrogen compound and a sulfur source as defined in U.S. Pat. Nos. 4,263,152, 4,265,773, 4,272,387, 4,285,822, 4,369,119, 4,395,343. Compounds prepared by reacting ammonium tetrathiomolybdate with a basic nitrogen compound as defined in U.S. Pat. No. 4,283,295. Compounds prepared by reacting an olefin, sulfur, an amine and a molybdenum source as defined in U.S. Pat. No. 4,362,633. Compounds prepared by reacting ammonium tetrathiomolybdate with a basic nitrogen compound and an organic sulfur source as defined in U.S. Pat. No. 4,402,840. Compounds prepared by reacting a phenolic compound, an amine and a molybdenum source with a sulfur source as defined in U.S. Pat. No. 4,466,901. Compounds prepared by reacting a triglyceride, a basic nitrogen compound, a molybdenum source, and a sulfur source as defined in U.S. Pat. No. 4,765,918. Compounds prepared by reacting alkali metal alkylthioxanthate salts with molybdenum halides as defined in U.S. Pat. No. 4,966,719. Compounds prepared by reacting a tetralkylthiuram disulfide with molybdenum hexacarbonyl as defined in U.S. Pat. No. 4,978,464. Compounds prepared by reacting an alkyl dixanthogen with molybdenum hexacarbonyl as defined in U.S. Pat. No. 4,990,271. Compounds prepared by reacting alkali metal alkylxanthate salts with dimolybdenum tetra-acetate as defined in U.S. Pat. No. 4,995,996. Compounds prepared by reacting (NH4)2Mo3S13*2H2O with an alkali metal dialkyidithiocarbamate or tetralkyl thiuram disulfide as define in U.S. Pat. No. 6,232,276. Compounds prepared by reacting an ester or acid with a diamine, a molybdenum source and carbon disulfide as defined in U.S. Pat. No. 6,103,674. Compounds prepared by reacting an alkali metal dialkyldithiocarbamate with 3-chloropropionic acid, followed by molybdenum trioxide, as defined in U.S. Pat. No. 6,117,826.
- Non-limiting examples of molybdenum-containing compounds include molybdenum carboxylates, molybdenum amides, molybdenum thiophosphates, molybdenum thiocarbamates, molybdenum dithiocarbamates, and so forth.
- Additional examples of ash-containing compounds include, but are not limited to, titanium-containing compounds and tungsten-containing compounds.
- Another suitable group of friction modifiers include non-nitrogen-containing compounds, such as polyolesters, for example, glycerol monooleate (GMO), glycerol monolaurate (GML), and the like.
- The friction modifying compound can be present in the lubricating composition in any desired or effective amount. In an aspect, the lubricating composition can comprise from about 0.05% to about 3% by weight, for example from about 0.2% to about 1.5%, and as a further example from about 0.3% to about 1% by weight relative to the total weight of the lubricating composition. However, one of ordinary skill in the art would understand that any amount can be used.
- The lubricating composition disclosed herein can comprise a base oil. Base oils suitable for use in formulating the disclosed compositions can be selected from any of the synthetic or mineral oils or mixtures thereof. Mineral oils include animal oils and vegetable oils (e.g., castor oil, lard oil) as well as other mineral lubricating oils such as liquid petroleum oils and solvent treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types. Oils derived from coal or shale are also suitable. Further, oils derived from a gas-to-liquid process are also suitable.
- The base oil can be present in a major amount, wherein “major amount” is understood to mean greater than or equal to 50%, for example from about 80 to about 98 percent by weight of the lubricant composition.
- The base oil typically has a viscosity of, for example, from about 2 to about 15 cSt and, as a further example, from about 2 to about 10 cSt at 100° C.
- Non-limiting examples of synthetic oils include hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene isobutylene copolymers, etc.); polyalphaolefins such as poly(1-hexenes), poly-(1-octenes), poly(1-decenes), etc. and mixtures thereof; alkylbenzenes (e.g., dodecylbenzenes, tetradecylbenzenes, di-nonylbenzenes, di-(2-ethylhexyl)benzenes, etc.); polyphenyls (e.g., biphenyls, terphenyl, alkylated polyphenyls, etc.); alkylated diphenyl ethers and alkylated diphenyl sulfides and the derivatives, analogs and homologs thereof and the like.
- Alkylene oxide polymers and interpolymers and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc., constitute another class of known synthetic oils that can be used. Such oils are exemplified by the oils prepared through polymerization of ethylene oxide or propylene oxide, the alkyl and aryl ethers of these polyoxyalkylene polymers (e.g., methyl-polyisopropylene glycol ether having an average molecular weight of about 1000, diphenyl ether of polyethylene glycol having a molecular weight of about 500-1000, diethyl ether of polypropylene glycol having a molecular weight of about 1000-1500, etc.) or mono- and polycarboxylic esters thereof, for example, the acetic acid esters, mixed C3-8 fatty acid esters, or the C13 Oxo acid diester of tetraethylene glycol.
- Another class of synthetic oils that can be used includes the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, alkenyl malonic acids, etc.) with a variety of alcohols (e.g., butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, propylene glycol, etc.) Specific examples of these esters include dibutyl adipate, di(2-ethylhexyl)sebacate, di-n-hexyl fumarate, dioctyl sebacate, diusooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid and the like.
- Esters useful as synthetic oils also include those made from C5-12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylol propane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
- Hence, the base oil used which can be used to make the compositions as described herein can be selected from any of the base oils in Groups I-V as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines. Such base oil groups are as follows:
- Group I contain less than 90% saturates and/or greater than 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120; Group II contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 80 and less than 120; Group III contain greater than or equal to 90% saturates and less than or equal to 0.03% sulfur and have a viscosity index greater than or equal to 120; Group IV are polyalphaolefins (PAO); and Group V include all other basestocks not included in Group I, II, III or IV.
- The test methods used in defining the above groups are ASTM D2007 for saturates; ASTM D2270 for viscosity index; and one of ASTM D2622, 4294, 4927 and 3120 for sulfur.
- Group IV basestocks, i.e. polyalphaolefins (PAO) include hydrogenated oligomers of an alpha-olefin, the most important methods of oligomerisation being free radical processes, Ziegler catalysis, and cationic, Friedel-Crafts catalysis.
- The polyalphaolefins typically have viscosities in the range of 2 to 100 cSt at 100° C., for example 4 to 8 cSt at 100° C. They can, for example, be oligomers of branched or straight chain alpha-olefins having from about 2 to about 30 carbon atoms, non-limiting examples include polypropenes, polyisobutenes, poly-1-butenes, poly-1-hexenes, poly-1-octenes and poly-1-decene. Included are homopolymers, interpolymers and mixtures.
- Regarding the balance of the basestock referred to above, a “Group I basestock” also includes a Group I basestock with which basestock(s) from one or more other groups can be admixed, provided that the resulting admixture has characteristics falling within those specified above for Group I basestocks.
- Exemplary basestocks include Group I basestocks and mixtures of Group II basestocks with Group I bright stock.
- Basestocks suitable for use herein can be made using a variety of different processes including but not limited to distillation, solvent refining, hydrogen processing, oligomerisation, esterification, and re-refining.
- The base oil can be an oil derived from Fischer-Tropsch synthesized hydrocarbons. Fischer-Tropsch synthesized hydrocarbons can be made from synthesis gas containing H2 and CO using a Fischer-Tropsch catalyst. Such hydrocarbons typically require further processing in order to be useful as the base oil. For example, the hydrocarbons can be hydroisomerized using processes disclosed in U.S. Pat. No. 6,103,099 or 6,180,575; hydrocracked and hydroisomerized using processes disclosed in U.S. Pat. No. 4,943,672 or 6,096,940; dewaxed using processes disclosed in U.S. Pat. No. 5,882,505; or hydroisomerized and dewaxed using processes disclosed in U.S. Pat. No. 6,013,171; 6,080,301; or 6,165,949.
- Unrefined, refined and rerefined oils, either mineral or synthetic (as well as mixtures of two or more of any of these) of the type disclosed hereinabove can be used in the base oils. Unrefined oils are those obtained directly from a mineral or synthetic source without further purification treatment. For example, a shale oil obtained directly from retorting operations, a petroleum oil obtained directly from primary distillation or ester oil obtained directly from an esterification process and used without further treatment would be an unrefined oil. Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties. Many such purification techniques are known to those skilled in the art such as solvent extraction, secondary distillation, acid or base extraction, filtration, percolation, etc. Rerefined oils are obtained by processes similar to those used to obtain refined oils applied to refined oils which have been already used in service. Such rerefined oils are also known as reclaimed or reprocessed oils and often are additionally processed by techniques directed to removal of spent additives, contaminants, and oil breakdown products.
- In an aspect, the lubricating composition can comprise less than about 325 ppm of boron. In a further aspect, the lubricating composition can comprise less than about 300 ppm of boron, and for example less than 280 ppm of boron.
- The disclosed lubricating composition can reduce boundary friction on a surface of a machine as compared to a surface that is not lubricated with the disclosed lubricating composition. In an aspect, the lubricating composition can be applied/provided to any surface of any machine, such as for example an engine, a gear, etc.
- Optionally, other components can be present in the lubricant composition. Non-limiting examples of other components include antiwear agents, dispersants, diluents, defoamers, demulsifiers, anti-foam agents, corrosion inhibitors, extreme pressure agents, seal well agents, antioxidants, pour point depressants, rust inhibitors and friction modifiers.
- Four dispersants (A-D) and two friction modifiers were blended/mixed/combined with base oil in various combinations to form lubricant compositions. The boundary friction coefficient of the resultant lubricant composition was determined using a high frequency reciprocating rig (HFRR) as described in SAE paper 961142 (January 1996), the disclosure of which is hereby incorporated by reference. The results are shown in Table 1.
-
TABLE 1 non- % nitrogen- molybdenum- Boundary Reduction B in Disp. A Disp. B containing containing Friction Friction oil (wt. % (wt. % compound compound Coeff. At Coeff. v. Example (ppm) active) active) (wt. %) (wt. %) 130° C. Compare 1 Compare 1 347 3.1 0.0 0.0 0.0 0.139 — Invention 1 0 0.0 3.1 0.0 0.0 0.121 13% Compare 2 347 3.1 0.0 0.5 0.0 0.102 27% Invention 2 0 0.0 3.1 0.5 0.0 0.075 46% Invention 3 174 1.55 1.55 0.5 0.0 0.090 35% Invention 4 87 0.77 2.33 0.5 0.0 0.078 44% Compare 3 347 3.1 0.0 0.0 0.5 0.103 26% Invention 5 0 0.0 3.1 0.0 0.5 0.088 36% Compare 4 347 3.1 0.0 0.0 0.8 0.097 30% Invention 6 0 0.0 3.1 0.0 0.8 0.054 61% Disp. C Disp. D Compare 5 295 2.5 0.0 0.3 0.05 0.109 22% Invention 7 0 0.0 2.5 0.3 0.05 0.088 37% Invention 8 74 0.63 1.88 0.3 0.05 0.083 40% Dispersant A - High vinylidene PIB based dispersant with TEPA as the amine and is boronated. Typical Analytical % N 1.1; TBN 16.6 mgKOH/g; % B 1.12 Dispersant B - Conventional PIB based dispersant with with TEPA as the amine. Typical Analytical % N 1.2; TBN 16.6 mgKOH/g Dispersant C - High vinylidene PIB based dispersant with E-100 as the amine and is boronated. Typical Analytical % N 1.52; TBN 32.7 mgKOH/g, % B 1.18 Dispersant D - High vinylidene PIB based dispersant with E-100 as the amine. Typical Analytical % N 1.95; TBN 41.4 mgKOH/g - The Comparative Example 1 and the Invention 1 results illustrated that in the absence of a friction modifier the use of a boron-containing dispersant (Dispersant A) produced a higher boundary friction coefficient as compared to non-boron containing dispersant (Dispersant B). In particular, Comparative Example 1 had 347 ppm of boron in the lubricant composition.
- The Comparative Example 2 illustrated that a non-nitrogen-containing compound reduced boundary friction by 27% as compared to Comparative Example 1, which did not contain a friction modifier. However, the combination of a non-nitrogen-containing compound and a non-boron-containing dispersant (Invention 2) reduced boundary friction by 46% as compared to Comparative Example 1. Moreover, mixtures of a boron-containing and a non-boron-containing compound with a non-nitrogen-containing compound (Inventions 3 and 4) produced lower boundary friction coefficients as compared to Comparative Example 2.
- Comparative Examples 3 and 4 illustrated that a molybdenum-containing compound and a boron-containing dispersant reduced boundary friction by 26% and 30%, respectively, as compared to the boron-containing dispersant alone (Comparative Example 1). However, the combination of a molybdenum-containing compound and a non-boron-containing dispersant (Inventions 5 and 6) reduced boundary friction by 36% and 61%, respectively.
- Comparative Example 5 illustrated that a combination of a boron-containing dispersant, a non-nitrogen-containing compound, and a molybdenum-containing compound reduced boundary friction by 22%, as compared to Comparative Example 1. However, Invention 7 illustrated that a combination of a non-boron-containing dispersant, a non-nitrogen-containing compound, and a molybdenum-containing compound reduced boundary friction by 37%, as compared to Comparative Example 1.
- At numerous places throughout this specification, reference has been made to a number of U.S. patents, published foreign patent applications and published technical papers. All such cited documents are expressly incorporated in full into this disclosure as if fully set forth herein.
- For the purposes of this specification and appended claims, unless otherwise indicated, all numbers expressing quantities, percentages or proportions, and other numerical values used in the specification and claims, are to be understood as being modified in all instances by the term “about.” Accordingly, unless indicated to the contrary, the numerical parameters set forth in the following specification and attached claims are approximations that can vary depending upon the desired properties sought to be obtained by the present disclosure. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.
- It is noted that, as used in this specification and the appended claims, the singular forms “a,” “an,” and “the,” include plural referents unless expressly and unequivocally limited to one referent. Thus, for example, reference to “an antioxidant” includes two or more different antioxidants. As used herein, the term “include” and its grammatical variants are intended to be non-limiting, such that recitation of items in a list is not to the exclusion of other like items that can be substituted or added to the listed items.
- While particular embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or can be presently unforeseen can arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they can be amended are intended to embrace all such alternatives, modifications variations, improvements, and substantial equivalents.
Claims (20)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/457,579 US20080015127A1 (en) | 2006-07-14 | 2006-07-14 | Boundary friction reducing lubricating composition |
DE102007030809A DE102007030809A1 (en) | 2006-07-14 | 2007-07-03 | Interface friction reducing lubricating composition |
JP2007178532A JP2008019438A (en) | 2006-07-14 | 2007-07-06 | Lubricant composition for decreasing boundary friction |
GB0910770A GB2460963B (en) | 2006-07-14 | 2007-07-06 | Boundary friction reducing lubricating composition |
GB0713197A GB2444135B (en) | 2006-07-14 | 2007-07-06 | Boundary friction reducing lubricant composition |
FR0756405A FR2903995B1 (en) | 2006-07-14 | 2007-07-11 | LIMITING FRICTION LIMITING LUBRICANT COMPOSITION AND PROCESS FOR PREPARING THE SAME. |
CNA2007101385069A CN101165148A (en) | 2006-07-14 | 2007-07-13 | Boundary friction reducing lubricating composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/457,579 US20080015127A1 (en) | 2006-07-14 | 2006-07-14 | Boundary friction reducing lubricating composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US20080015127A1 true US20080015127A1 (en) | 2008-01-17 |
Family
ID=38440562
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/457,579 Abandoned US20080015127A1 (en) | 2006-07-14 | 2006-07-14 | Boundary friction reducing lubricating composition |
Country Status (6)
Country | Link |
---|---|
US (1) | US20080015127A1 (en) |
JP (1) | JP2008019438A (en) |
CN (1) | CN101165148A (en) |
DE (1) | DE102007030809A1 (en) |
FR (1) | FR2903995B1 (en) |
GB (2) | GB2444135B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2248878A1 (en) | 2009-05-01 | 2010-11-10 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
EP2441818A1 (en) | 2010-10-12 | 2012-04-18 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2717752T3 (en) * | 2013-12-05 | 2019-06-25 | Infineum Int Ltd | A composition of lubricating oil for gas engines |
Citations (95)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2284410A (en) * | 1940-08-22 | 1942-05-26 | John F Farmer | Adjustable end slide grille |
US2284409A (en) * | 1940-03-08 | 1942-05-26 | Pittsburgh Corning Corp | Fitting for tempered glass panels |
US2459112A (en) * | 1945-07-06 | 1949-01-11 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2984550A (en) * | 1956-09-06 | 1961-05-16 | Nalco Chemical Co | Color stabilization of petroleum oils and compositions therefor |
US3036003A (en) * | 1957-08-07 | 1962-05-22 | Sinclair Research Inc | Lubricating oil composition |
US3087936A (en) * | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3127351A (en) * | 1964-03-31 | Xxvii | ||
US3166516A (en) * | 1960-10-28 | 1965-01-19 | Nalco Chemical Co | Process for breaking petroleum emulsions |
US3172892A (en) * | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3184474A (en) * | 1962-09-05 | 1965-05-18 | Exxon Research Engineering Co | Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial |
US3236770A (en) * | 1960-09-28 | 1966-02-22 | Sinclair Research Inc | Transaxle lubricant |
US3306908A (en) * | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3316177A (en) * | 1964-12-07 | 1967-04-25 | Lubrizol Corp | Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene |
US3368972A (en) * | 1965-01-06 | 1968-02-13 | Mobil Oil Corp | High molecular weight mannich bases as engine oil additives |
US3381022A (en) * | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
US3433744A (en) * | 1966-11-03 | 1969-03-18 | Lubrizol Corp | Reaction product of phosphosulfurized hydrocarbon and alkylene polycarboxylic acid or acid derivatives and lubricating oil containing the same |
US3438757A (en) * | 1965-08-23 | 1969-04-15 | Chevron Res | Hydrocarbyl amines for fuel detergents |
US3442808A (en) * | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
US3444170A (en) * | 1959-03-30 | 1969-05-13 | Lubrizol Corp | Process which comprises reacting a carboxylic intermediate with an amine |
US3448048A (en) * | 1967-01-23 | 1969-06-03 | Lubrizol Corp | Lubricant containing a high molecular weight acylated amine |
US3448047A (en) * | 1967-04-05 | 1969-06-03 | Standard Oil Co | Lube oil dispersants |
US3448049A (en) * | 1967-09-22 | 1969-06-03 | Rohm & Haas | Polyolefinic succinates |
US3449250A (en) * | 1962-05-14 | 1969-06-10 | Monsanto Co | Dispersency oil additives |
US3451933A (en) * | 1967-08-11 | 1969-06-24 | Rohm & Haas | Formamido-containing alkenylsuccinates |
US3493520A (en) * | 1968-06-04 | 1970-02-03 | Sinclair Research Inc | Ashless lubricating oil detergents |
US3501405A (en) * | 1967-08-11 | 1970-03-17 | Rohm & Haas | Lubricating and fuel compositions comprising copolymers of n-substituted formamide-containing unsaturated esters |
US3509051A (en) * | 1964-08-07 | 1970-04-28 | T R Vanderbilt Co Inc | Lubricating compositions containing sulfurized oxymolybdenum dithiocarbamates |
US3558743A (en) * | 1968-06-04 | 1971-01-26 | Joseph A Verdol | Ashless,oil-soluble detergents |
US3567637A (en) * | 1969-04-02 | 1971-03-02 | Standard Oil Co | Method of preparing over-based alkaline earth long-chain alkenyl succinates |
US3574101A (en) * | 1968-04-29 | 1971-04-06 | Lubrizol Corp | Acylating agents,their salts,and lubricants and fuels containing the same |
US3576743A (en) * | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
US3586629A (en) * | 1968-09-16 | 1971-06-22 | Mobil Oil Corp | Metal salts as lubricant additives |
US3632511A (en) * | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
US3632904A (en) * | 1970-03-24 | 1972-01-04 | Paul Mauz | Moving coil loudspeaker with eddy current suppression |
US3632510A (en) * | 1963-04-23 | 1972-01-04 | Lubrizol Corp | Mixed ester-metal salts and lubricants and fuels containing the same |
US3634515A (en) * | 1968-11-08 | 1972-01-11 | Standard Oil Co | Alkylene polyamide formaldehyde |
US3649229A (en) * | 1969-12-17 | 1972-03-14 | Mobil Oil Corp | Liquid hydrocarbon fuels containing high molecular weight mannich bases |
US3658836A (en) * | 1964-04-16 | 1972-04-25 | Monsanto Co | Hydroxyboroxin-amine salts |
US3666730A (en) * | 1967-09-19 | 1972-05-30 | Lubrizol Corp | Oil-soluble interpolymers of n-vinylthiopyrrolidones |
US3718663A (en) * | 1967-11-24 | 1973-02-27 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product |
US3725480A (en) * | 1968-11-08 | 1973-04-03 | Standard Oil Co | Ashless oil additives |
US3725277A (en) * | 1966-01-26 | 1973-04-03 | Ethyl Corp | Lubricant compositions |
US3725441A (en) * | 1968-04-29 | 1973-04-03 | Lubrizol Corp | Acylating agents, their salts, and lubricants and fuels containing the same |
US3726882A (en) * | 1968-11-08 | 1973-04-10 | Standard Oil Co | Ashless oil additives |
US3736357A (en) * | 1965-10-22 | 1973-05-29 | Standard Oil Co | High molecular weight mannich condensation products from two different alkyl-substituted hydroxy-aromatic compounds |
US3793202A (en) * | 1972-03-01 | 1974-02-19 | Standard Oil Co | Oil solution of aliphatic acid and aliphatic aldehyde modified high molecular weight mannich reaction products |
US3798247A (en) * | 1970-07-13 | 1974-03-19 | Standard Oil Co | Oil soluble aliphatic acid derivatives of molecular weight mannich condensation products |
US3798165A (en) * | 1965-10-22 | 1974-03-19 | Standard Oil Co | Lubricating oils containing high molecular weight mannich condensation products |
US3803039A (en) * | 1970-07-13 | 1974-04-09 | Standard Oil Co | Oil solution of aliphatic acid derivatives of high molecular weight mannich condensation product |
US3804763A (en) * | 1971-07-01 | 1974-04-16 | Lubrizol Corp | Dispersant compositions |
US3862981A (en) * | 1971-07-08 | 1975-01-28 | Rhone Progil | New lubricating oil additives |
US3872019A (en) * | 1972-08-08 | 1975-03-18 | Standard Oil Co | Oil-soluble lubricant bi-functional additives from mannich condensation products of oxidized olefin copolymers, amines and aldehydes |
US3936480A (en) * | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
US3950341A (en) * | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
US3957854A (en) * | 1971-06-11 | 1976-05-18 | The Lubrizol Corporation | Ester-containing compositions |
US3957855A (en) * | 1971-06-11 | 1976-05-18 | The Lubrizol Corporation | Ester-containing compositions |
US3957746A (en) * | 1974-10-04 | 1976-05-18 | Ethyl Corporation | Phospho-sulfurized phenolic aldehyde amine alkylene oxide condensation product |
US4006089A (en) * | 1974-11-19 | 1977-02-01 | Mobil Oil Corporation | Polyoxyethylene polyamine Mannich base products and use of same in fuels and lubricants |
US4011380A (en) * | 1975-12-05 | 1977-03-08 | Standard Oil Company (Indiana) | Oxidation of polymers in presence of benzene sulfonic acid or salt thereof |
US4025451A (en) * | 1973-09-14 | 1977-05-24 | Ethyl Corporation | Sulfurized mannich bases as lubricating oil dispersant |
US4071548A (en) * | 1971-11-30 | 1978-01-31 | Toa Nenryo Kogyo Kabushiki Kaisha | Lubricating oil additive, process for the synthesis thereof and lubricating oil additive composition |
US4090854A (en) * | 1974-11-29 | 1978-05-23 | The Lubrizol Corporation | Sulfurized Mannich condensation products and fuel compositions containing same |
US4259195A (en) * | 1979-06-28 | 1981-03-31 | Chevron Research Company | Reaction product of acidic molybdenum compound with basic nitrogen compound and lubricants containing same |
US4261843A (en) * | 1979-06-28 | 1981-04-14 | Chevron Research Company | Reaction product of acidic molybdenum compound with basic nitrogen compound and lubricants containing same |
US4263152A (en) * | 1979-06-28 | 1981-04-21 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4265773A (en) * | 1979-06-28 | 1981-05-05 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4266945A (en) * | 1979-11-23 | 1981-05-12 | The Lubrizol Corporation | Molybdenum-containing compositions and lubricants and fuels containing them |
US4272387A (en) * | 1979-06-28 | 1981-06-09 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4369119A (en) * | 1981-04-03 | 1983-01-18 | Chevron Research Company | Antioxidant combinations of molybdenum complexes and organic sulfur compounds for lubricating oils |
US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
US4652387A (en) * | 1986-07-30 | 1987-03-24 | Mobil Oil Corporation | Borated reaction products of succinic compounds as lubricant dispersants and antioxidants |
US4990271A (en) * | 1989-09-07 | 1991-02-05 | Exxon Research And Engineering Company | Antiwear, antioxidant and friction reducing additive for lubricating oils |
US4995996A (en) * | 1989-12-14 | 1991-02-26 | Exxon Research And Engineering Company | Molybdenum sulfur antiwear and antioxidant lube additives |
US5282991A (en) * | 1988-02-26 | 1994-02-01 | Exxon Chemical Patents Inc. | Friction modified oleaginous concentrates of improved stability |
US5412130A (en) * | 1994-06-08 | 1995-05-02 | R. T. Vanderbilt Company, Inc. | Method for preparation of organic molybdenum compounds |
US5634951A (en) * | 1996-06-07 | 1997-06-03 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
US5725612A (en) * | 1996-06-07 | 1998-03-10 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
US5763372A (en) * | 1996-12-13 | 1998-06-09 | Ethyl Corporation | Clean gear boron-free gear additive and method for producing same |
US5882505A (en) * | 1997-06-03 | 1999-03-16 | Exxon Research And Engineering Company | Conversion of fisher-tropsch waxes to lubricants by countercurrent processing |
US5891786A (en) * | 1995-01-12 | 1999-04-06 | Ethyl Corporation | Substantially metal free synthetic power transmission fluids having enhanced performance capabilities |
US6013171A (en) * | 1998-02-03 | 2000-01-11 | Exxon Research And Engineering Co. | Catalytic dewaxing with trivalent rare earth metal ion exchanged ferrierite |
US6080301A (en) * | 1998-09-04 | 2000-06-27 | Exxonmobil Research And Engineering Company | Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins |
US6180575B1 (en) * | 1998-08-04 | 2001-01-30 | Mobil Oil Corporation | High performance lubricating oils |
US6232276B1 (en) * | 1996-12-13 | 2001-05-15 | Infineum Usa L.P. | Trinuclear molybdenum multifunctional additive for lubricating oils |
US20020072478A1 (en) * | 2000-09-29 | 2002-06-13 | Nippon Mitsubishi Oil Corporation | Lubricant compositions |
US6528461B1 (en) * | 2000-11-28 | 2003-03-04 | Bank Of America, N.A. | Lubricant containing molybdenum and polymeric dispersant |
US20040077506A1 (en) * | 2002-10-22 | 2004-04-22 | Stephen Arrowsmith | Lubricating oil compositions |
US20050043191A1 (en) * | 2003-08-22 | 2005-02-24 | Farng L. Oscar | High performance non-zinc, zero phosphorus engine oils for internal combustion engines |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
US20050124509A1 (en) * | 2003-12-04 | 2005-06-09 | Antonio Gutierrez | Lubricating oil compositions |
US20060094607A1 (en) * | 2004-11-04 | 2006-05-04 | Devlin Mark T | Lubricating composition |
US20060105921A1 (en) * | 2002-11-05 | 2006-05-18 | Naozumi Arimoto | Lubricating oil |
US20080051305A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant composition |
US20080051304A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant compositions |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1336902C (en) * | 1988-02-26 | 1995-09-05 | Jacob Emert | Friction modified oleaginous concentrates of improved stability |
JPH07150170A (en) * | 1993-11-30 | 1995-06-13 | Tonen Corp | Lubricating oil composition |
JPH08209178A (en) * | 1995-02-02 | 1996-08-13 | Tonen Corp | Lubricant composition |
JP2000273480A (en) * | 1999-03-29 | 2000-10-03 | Asahi Denka Kogyo Kk | Lubricating composition |
JP4856305B2 (en) * | 2000-10-30 | 2012-01-18 | Jx日鉱日石エネルギー株式会社 | Engine oil composition |
US6730638B2 (en) * | 2002-01-31 | 2004-05-04 | Exxonmobil Research And Engineering Company | Low ash, low phosphorus and low sulfur engine oils for internal combustion engines |
JP3594194B1 (en) * | 2003-08-21 | 2004-11-24 | 新日本石油株式会社 | Low friction sliding mechanism and lubricating oil composition used therefor |
US20050065043A1 (en) * | 2003-09-23 | 2005-03-24 | Henly Timothy J. | Power transmission fluids having extended durability |
US20050070446A1 (en) * | 2003-09-25 | 2005-03-31 | Ethyl Petroleum Additives, Inc. | Boron free automotive gear oil |
US7452851B2 (en) * | 2003-10-24 | 2008-11-18 | Afton Chemical Corporation | Lubricant compositions |
US7759294B2 (en) * | 2003-10-24 | 2010-07-20 | Afton Chemical Corporation | Lubricant compositions |
GB0326808D0 (en) * | 2003-11-18 | 2003-12-24 | Infineum Int Ltd | Lubricating oil composition |
US7419940B2 (en) * | 2003-12-19 | 2008-09-02 | Exxonmobil Research And Engineering Company | Borated-epoxidized polybutenes as low-ash anti-wear additives for lubricants |
US20060264340A1 (en) * | 2005-05-20 | 2006-11-23 | Iyer Ramnath N | Fluid compositions for dual clutch transmissions |
EP1724330B1 (en) * | 2005-05-20 | 2011-05-25 | Infineum International Limited | Use of lubricating oil compositions to reduce wear in passenger car motor engines having a rotating tappet |
US20070105728A1 (en) * | 2005-11-09 | 2007-05-10 | Phillips Ronald L | Lubricant composition |
-
2006
- 2006-07-14 US US11/457,579 patent/US20080015127A1/en not_active Abandoned
-
2007
- 2007-07-03 DE DE102007030809A patent/DE102007030809A1/en not_active Withdrawn
- 2007-07-06 JP JP2007178532A patent/JP2008019438A/en active Pending
- 2007-07-06 GB GB0713197A patent/GB2444135B/en not_active Expired - Fee Related
- 2007-07-06 GB GB0910770A patent/GB2460963B/en not_active Expired - Fee Related
- 2007-07-11 FR FR0756405A patent/FR2903995B1/en not_active Expired - Fee Related
- 2007-07-13 CN CNA2007101385069A patent/CN101165148A/en active Pending
Patent Citations (99)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3127351A (en) * | 1964-03-31 | Xxvii | ||
US2284409A (en) * | 1940-03-08 | 1942-05-26 | Pittsburgh Corning Corp | Fitting for tempered glass panels |
US2284410A (en) * | 1940-08-22 | 1942-05-26 | John F Farmer | Adjustable end slide grille |
US2459112A (en) * | 1945-07-06 | 1949-01-11 | Socony Vacuum Oil Co Inc | Mineral oil composition |
US2984550A (en) * | 1956-09-06 | 1961-05-16 | Nalco Chemical Co | Color stabilization of petroleum oils and compositions therefor |
US3036003A (en) * | 1957-08-07 | 1962-05-22 | Sinclair Research Inc | Lubricating oil composition |
US3172892A (en) * | 1959-03-30 | 1965-03-09 | Reaction product of high molecular weight succinic acids and succinic anhydrides with an ethylene poly- amine | |
US3444170A (en) * | 1959-03-30 | 1969-05-13 | Lubrizol Corp | Process which comprises reacting a carboxylic intermediate with an amine |
US3236770A (en) * | 1960-09-28 | 1966-02-22 | Sinclair Research Inc | Transaxle lubricant |
US3166516A (en) * | 1960-10-28 | 1965-01-19 | Nalco Chemical Co | Process for breaking petroleum emulsions |
US3087936A (en) * | 1961-08-18 | 1963-04-30 | Lubrizol Corp | Reaction product of an aliphatic olefinpolymer-succinic acid producing compound with an amine and reacting the resulting product with a boron compound |
US3254025A (en) * | 1961-08-18 | 1966-05-31 | Lubrizol Corp | Boron-containing acylated amine and lubricating compositions containing the same |
US3449250A (en) * | 1962-05-14 | 1969-06-10 | Monsanto Co | Dispersency oil additives |
US3184474A (en) * | 1962-09-05 | 1965-05-18 | Exxon Research Engineering Co | Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial |
US3381022A (en) * | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
US3632510A (en) * | 1963-04-23 | 1972-01-04 | Lubrizol Corp | Mixed ester-metal salts and lubricants and fuels containing the same |
US3306908A (en) * | 1963-12-26 | 1967-02-28 | Lubrizol Corp | Reaction products of high molecular weight hydrocarbon succinic compounds, amines and heavy metal compounds |
US3658836A (en) * | 1964-04-16 | 1972-04-25 | Monsanto Co | Hydroxyboroxin-amine salts |
US3311558A (en) * | 1964-05-19 | 1967-03-28 | Rohm & Haas | N-alkylmorpholinone esters of alkenylsuccinic anhydrides |
US3509051A (en) * | 1964-08-07 | 1970-04-28 | T R Vanderbilt Co Inc | Lubricating compositions containing sulfurized oxymolybdenum dithiocarbamates |
US3316177A (en) * | 1964-12-07 | 1967-04-25 | Lubrizol Corp | Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene |
US3368972A (en) * | 1965-01-06 | 1968-02-13 | Mobil Oil Corp | High molecular weight mannich bases as engine oil additives |
US3438757A (en) * | 1965-08-23 | 1969-04-15 | Chevron Res | Hydrocarbyl amines for fuel detergents |
US3565804A (en) * | 1965-08-23 | 1971-02-23 | Chevron Res | Lubricating oil additives |
US3798165A (en) * | 1965-10-22 | 1974-03-19 | Standard Oil Co | Lubricating oils containing high molecular weight mannich condensation products |
US3736357A (en) * | 1965-10-22 | 1973-05-29 | Standard Oil Co | High molecular weight mannich condensation products from two different alkyl-substituted hydroxy-aromatic compounds |
US3725277A (en) * | 1966-01-26 | 1973-04-03 | Ethyl Corp | Lubricant compositions |
US3442808A (en) * | 1966-11-01 | 1969-05-06 | Standard Oil Co | Lubricating oil additives |
US3433744A (en) * | 1966-11-03 | 1969-03-18 | Lubrizol Corp | Reaction product of phosphosulfurized hydrocarbon and alkylene polycarboxylic acid or acid derivatives and lubricating oil containing the same |
US3448048A (en) * | 1967-01-23 | 1969-06-03 | Lubrizol Corp | Lubricant containing a high molecular weight acylated amine |
US3448047A (en) * | 1967-04-05 | 1969-06-03 | Standard Oil Co | Lube oil dispersants |
US3501405A (en) * | 1967-08-11 | 1970-03-17 | Rohm & Haas | Lubricating and fuel compositions comprising copolymers of n-substituted formamide-containing unsaturated esters |
US3451933A (en) * | 1967-08-11 | 1969-06-24 | Rohm & Haas | Formamido-containing alkenylsuccinates |
US3666730A (en) * | 1967-09-19 | 1972-05-30 | Lubrizol Corp | Oil-soluble interpolymers of n-vinylthiopyrrolidones |
US3448049A (en) * | 1967-09-22 | 1969-06-03 | Rohm & Haas | Polyolefinic succinates |
US3718663A (en) * | 1967-11-24 | 1973-02-27 | Standard Oil Co | Preparation of oil-soluble boron derivatives of an alkylene polyamine-urea or thiourea-succinic anhydride addition product |
US3725441A (en) * | 1968-04-29 | 1973-04-03 | Lubrizol Corp | Acylating agents, their salts, and lubricants and fuels containing the same |
US3574101A (en) * | 1968-04-29 | 1971-04-06 | Lubrizol Corp | Acylating agents,their salts,and lubricants and fuels containing the same |
US3493520A (en) * | 1968-06-04 | 1970-02-03 | Sinclair Research Inc | Ashless lubricating oil detergents |
US3558743A (en) * | 1968-06-04 | 1971-01-26 | Joseph A Verdol | Ashless,oil-soluble detergents |
US3586629A (en) * | 1968-09-16 | 1971-06-22 | Mobil Oil Corp | Metal salts as lubricant additives |
US3725480A (en) * | 1968-11-08 | 1973-04-03 | Standard Oil Co | Ashless oil additives |
US3634515A (en) * | 1968-11-08 | 1972-01-11 | Standard Oil Co | Alkylene polyamide formaldehyde |
US3726882A (en) * | 1968-11-08 | 1973-04-10 | Standard Oil Co | Ashless oil additives |
US3567637A (en) * | 1969-04-02 | 1971-03-02 | Standard Oil Co | Method of preparing over-based alkaline earth long-chain alkenyl succinates |
US3576743A (en) * | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
US3632511A (en) * | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
US3649229A (en) * | 1969-12-17 | 1972-03-14 | Mobil Oil Corp | Liquid hydrocarbon fuels containing high molecular weight mannich bases |
US3632904A (en) * | 1970-03-24 | 1972-01-04 | Paul Mauz | Moving coil loudspeaker with eddy current suppression |
US3798247A (en) * | 1970-07-13 | 1974-03-19 | Standard Oil Co | Oil soluble aliphatic acid derivatives of molecular weight mannich condensation products |
US3803039A (en) * | 1970-07-13 | 1974-04-09 | Standard Oil Co | Oil solution of aliphatic acid derivatives of high molecular weight mannich condensation product |
US3957854A (en) * | 1971-06-11 | 1976-05-18 | The Lubrizol Corporation | Ester-containing compositions |
US3957855A (en) * | 1971-06-11 | 1976-05-18 | The Lubrizol Corporation | Ester-containing compositions |
US3804763A (en) * | 1971-07-01 | 1974-04-16 | Lubrizol Corp | Dispersant compositions |
US3948800A (en) * | 1971-07-01 | 1976-04-06 | The Lubrizol Corporation | Dispersant compositions |
US3862981A (en) * | 1971-07-08 | 1975-01-28 | Rhone Progil | New lubricating oil additives |
US3936480A (en) * | 1971-07-08 | 1976-02-03 | Rhone-Progil | Additives for improving the dispersing properties of lubricating oil |
US4071548A (en) * | 1971-11-30 | 1978-01-31 | Toa Nenryo Kogyo Kabushiki Kaisha | Lubricating oil additive, process for the synthesis thereof and lubricating oil additive composition |
US3793202A (en) * | 1972-03-01 | 1974-02-19 | Standard Oil Co | Oil solution of aliphatic acid and aliphatic aldehyde modified high molecular weight mannich reaction products |
US3872019A (en) * | 1972-08-08 | 1975-03-18 | Standard Oil Co | Oil-soluble lubricant bi-functional additives from mannich condensation products of oxidized olefin copolymers, amines and aldehydes |
US3950341A (en) * | 1973-04-12 | 1976-04-13 | Toa Nenryo Kogyo Kabushiki Kaisha | Reaction product of a polyalkenyl succinic acid or its anhydride, a hindered alcohol and an amine |
US4025451A (en) * | 1973-09-14 | 1977-05-24 | Ethyl Corporation | Sulfurized mannich bases as lubricating oil dispersant |
US3957746A (en) * | 1974-10-04 | 1976-05-18 | Ethyl Corporation | Phospho-sulfurized phenolic aldehyde amine alkylene oxide condensation product |
US4006089A (en) * | 1974-11-19 | 1977-02-01 | Mobil Oil Corporation | Polyoxyethylene polyamine Mannich base products and use of same in fuels and lubricants |
US4083699A (en) * | 1974-11-19 | 1978-04-11 | Mobil Oil Corporation | Polyoxyethylene polyamine Mannich base products and use of same in fuels and lubricants |
US4090854A (en) * | 1974-11-29 | 1978-05-23 | The Lubrizol Corporation | Sulfurized Mannich condensation products and fuel compositions containing same |
US4011380A (en) * | 1975-12-05 | 1977-03-08 | Standard Oil Company (Indiana) | Oxidation of polymers in presence of benzene sulfonic acid or salt thereof |
US4259195A (en) * | 1979-06-28 | 1981-03-31 | Chevron Research Company | Reaction product of acidic molybdenum compound with basic nitrogen compound and lubricants containing same |
US4261843A (en) * | 1979-06-28 | 1981-04-14 | Chevron Research Company | Reaction product of acidic molybdenum compound with basic nitrogen compound and lubricants containing same |
US4263152A (en) * | 1979-06-28 | 1981-04-21 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4265773A (en) * | 1979-06-28 | 1981-05-05 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4272387A (en) * | 1979-06-28 | 1981-06-09 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4266945A (en) * | 1979-11-23 | 1981-05-12 | The Lubrizol Corporation | Molybdenum-containing compositions and lubricants and fuels containing them |
US4369119A (en) * | 1981-04-03 | 1983-01-18 | Chevron Research Company | Antioxidant combinations of molybdenum complexes and organic sulfur compounds for lubricating oils |
US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
US4652387A (en) * | 1986-07-30 | 1987-03-24 | Mobil Oil Corporation | Borated reaction products of succinic compounds as lubricant dispersants and antioxidants |
US5282991A (en) * | 1988-02-26 | 1994-02-01 | Exxon Chemical Patents Inc. | Friction modified oleaginous concentrates of improved stability |
US4990271A (en) * | 1989-09-07 | 1991-02-05 | Exxon Research And Engineering Company | Antiwear, antioxidant and friction reducing additive for lubricating oils |
US4995996A (en) * | 1989-12-14 | 1991-02-26 | Exxon Research And Engineering Company | Molybdenum sulfur antiwear and antioxidant lube additives |
US5412130A (en) * | 1994-06-08 | 1995-05-02 | R. T. Vanderbilt Company, Inc. | Method for preparation of organic molybdenum compounds |
US5891786A (en) * | 1995-01-12 | 1999-04-06 | Ethyl Corporation | Substantially metal free synthetic power transmission fluids having enhanced performance capabilities |
US5634951A (en) * | 1996-06-07 | 1997-06-03 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
US5725612A (en) * | 1996-06-07 | 1998-03-10 | Ethyl Corporation | Additives for minimizing intake valve deposits, and their use |
US5763372A (en) * | 1996-12-13 | 1998-06-09 | Ethyl Corporation | Clean gear boron-free gear additive and method for producing same |
US6232276B1 (en) * | 1996-12-13 | 2001-05-15 | Infineum Usa L.P. | Trinuclear molybdenum multifunctional additive for lubricating oils |
US5882505A (en) * | 1997-06-03 | 1999-03-16 | Exxon Research And Engineering Company | Conversion of fisher-tropsch waxes to lubricants by countercurrent processing |
US6013171A (en) * | 1998-02-03 | 2000-01-11 | Exxon Research And Engineering Co. | Catalytic dewaxing with trivalent rare earth metal ion exchanged ferrierite |
US6180575B1 (en) * | 1998-08-04 | 2001-01-30 | Mobil Oil Corporation | High performance lubricating oils |
US6080301A (en) * | 1998-09-04 | 2000-06-27 | Exxonmobil Research And Engineering Company | Premium synthetic lubricant base stock having at least 95% non-cyclic isoparaffins |
US20020072478A1 (en) * | 2000-09-29 | 2002-06-13 | Nippon Mitsubishi Oil Corporation | Lubricant compositions |
US6528461B1 (en) * | 2000-11-28 | 2003-03-04 | Bank Of America, N.A. | Lubricant containing molybdenum and polymeric dispersant |
US20040077506A1 (en) * | 2002-10-22 | 2004-04-22 | Stephen Arrowsmith | Lubricating oil compositions |
US20060105921A1 (en) * | 2002-11-05 | 2006-05-18 | Naozumi Arimoto | Lubricating oil |
US20050043191A1 (en) * | 2003-08-22 | 2005-02-24 | Farng L. Oscar | High performance non-zinc, zero phosphorus engine oils for internal combustion engines |
US20050101494A1 (en) * | 2003-11-10 | 2005-05-12 | Iyer Ramnath N. | Lubricant compositions for power transmitting fluids |
US20050124509A1 (en) * | 2003-12-04 | 2005-06-09 | Antonio Gutierrez | Lubricating oil compositions |
US20060094607A1 (en) * | 2004-11-04 | 2006-05-04 | Devlin Mark T | Lubricating composition |
US20080051305A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant composition |
US20080051304A1 (en) * | 2006-08-28 | 2008-02-28 | Devlin Mark T | Lubricant compositions |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2248878A1 (en) | 2009-05-01 | 2010-11-10 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
EP2441818A1 (en) | 2010-10-12 | 2012-04-18 | Shell Internationale Research Maatschappij B.V. | Lubricating composition |
Also Published As
Publication number | Publication date |
---|---|
FR2903995B1 (en) | 2011-03-11 |
GB0713197D0 (en) | 2007-08-15 |
DE102007030809A1 (en) | 2008-01-17 |
GB2460963B (en) | 2010-06-30 |
GB0910770D0 (en) | 2009-08-05 |
CN101165148A (en) | 2008-04-23 |
JP2008019438A (en) | 2008-01-31 |
FR2903995A1 (en) | 2008-01-25 |
GB2460963A (en) | 2009-12-23 |
GB2444135A (en) | 2008-05-28 |
GB2444135B (en) | 2009-12-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8557752B2 (en) | Lubricating compositions | |
US7767632B2 (en) | Additives and lubricant formulations having improved antiwear properties | |
US7709423B2 (en) | Additives and lubricant formulations for providing friction modification | |
US20080090743A1 (en) | Compounds and methods of making the compounds | |
EP1568759B1 (en) | Power transmission fluids | |
CA2872851C (en) | Lubricant additive for improving piston deposit control and emulsion stability | |
EP1645616A1 (en) | Power transmission fluids with enhanced antishudder durability | |
GB2448022A (en) | Lubricating oil composition for improved oxidation, viscosity increase, oil consumption and piston deposit control | |
US20060276351A1 (en) | Molybdenum-containing lubricant for improved power or fuel economy | |
JP2008094841A (en) | Branched succinimide dispersant compound and method for producing the compound | |
US20080015127A1 (en) | Boundary friction reducing lubricating composition | |
US20120108478A1 (en) | Lubricant composition suitable for engines fueled by alternate fuels | |
EP2361297A1 (en) | Reducing high-aqueous content sludge in diesel engines | |
EP1710295A1 (en) | Tractor fluids | |
JP7320991B2 (en) | Lubricant compositions and their dispersants that have a beneficial effect on oxidation stability | |
US20050101496A1 (en) | Hydrocarbyl dispersants and compositions containing the dispersants | |
AU2003293266B2 (en) | Molybdenum-containing lubricant for improved power or fuel economy | |
JP2006524263A5 (en) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: AFTON CHEMICAL CORPORATION, VIRGINIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LOPER, JOHN T.;LAM, WILLIAM Y.;DEVLIN, MARK T.;REEL/FRAME:018201/0624;SIGNING DATES FROM 20060712 TO 20060713 Owner name: AFTON CHEMICAL CORPORATION, VIRGINIA Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LOPER, JOHN T.;LAM, WILLIAM Y.;DEVLIN, MARK T.;REEL/FRAME:017937/0131;SIGNING DATES FROM 20060712 TO 20060713 |
|
AS | Assignment |
Owner name: SUNTRUST BANK, VIRGINIA Free format text: SECURITY AGREEMENT;ASSIGNOR:AFTON CHEMICAL CORPORATION;REEL/FRAME:018883/0865 Effective date: 20061221 Owner name: SUNTRUST BANK,VIRGINIA Free format text: SECURITY AGREEMENT;ASSIGNOR:AFTON CHEMICAL CORPORATION;REEL/FRAME:018883/0865 Effective date: 20061221 |
|
AS | Assignment |
Owner name: AFTON CHEMICAL CORPORATION, VIRGINIA Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:SUNTRUST BANK;REEL/FRAME:026707/0563 Effective date: 20110513 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |