US20050070446A1 - Boron free automotive gear oil - Google Patents

Boron free automotive gear oil Download PDF

Info

Publication number
US20050070446A1
US20050070446A1 US10/670,580 US67058003A US2005070446A1 US 20050070446 A1 US20050070446 A1 US 20050070446A1 US 67058003 A US67058003 A US 67058003A US 2005070446 A1 US2005070446 A1 US 2005070446A1
Authority
US
United States
Prior art keywords
oil
additive package
lubricating
oil soluble
test
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
Application number
US10/670,580
Other languages
English (en)
Inventor
Chip Hewette
Jeffrey Milner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Afton Chemical Corp
Original Assignee
Afton Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US10/670,580 priority Critical patent/US20050070446A1/en
Application filed by Afton Chemical Corp filed Critical Afton Chemical Corp
Assigned to ETHYL PETROLEUM ADDITIVES, INC. reassignment ETHYL PETROLEUM ADDITIVES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HEWETTE, CHIP, MILNER, JEFFREY L.
Assigned to SUNTRUST BANK, AS ADMINISTRATIVE AGENT reassignment SUNTRUST BANK, AS ADMINISTRATIVE AGENT SECURITY AGREEMENT Assignors: ETHYL PETROLEUM ADDITIVES, INC.
Priority to CA002480114A priority patent/CA2480114A1/en
Priority to AU2004210592A priority patent/AU2004210592A1/en
Priority to EP04077548A priority patent/EP1518919A1/en
Priority to JP2004272174A priority patent/JP2005097615A/ja
Priority to MXPA04009160A priority patent/MXPA04009160A/es
Priority to SG200405365A priority patent/SG110161A1/en
Assigned to AFTON CHEMICAL CORPORATION reassignment AFTON CHEMICAL CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: ETHYL PETROLEUM ADDITIVES, INC.
Publication of US20050070446A1 publication Critical patent/US20050070446A1/en
Priority to US11/552,733 priority patent/US20070054813A1/en
Assigned to SUNTRUST BANK reassignment SUNTRUST BANK SECURITY AGREEMENT Assignors: AFTON CHEMICAL CORPORATION
Assigned to AFTON CHEMICAL CORPORATION reassignment AFTON CHEMICAL CORPORATION RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: SUNTRUST BANK
Priority to JP2011270247A priority patent/JP2012046769A/ja
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more 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
    • C10M2215/22—Heterocyclic nitrogen compounds
    • C10M2215/223—Five-membered rings containing nitrogen and carbon only
    • 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms 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
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40—Low content or no content compositions
    • C10N2030/42—Phosphor free or low phosphor content compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/40—Low content or no content compositions
    • C10N2030/44—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
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives

Definitions

  • the present invention is in the field of lubricant additives and lubricant formulations. Specifically, the present invention relates to a boron-free lubricant additive package that is capable of passing tests for which the presence of boron was thought to be essential to passing.
  • boron-containing lubricants have been used to attain satisfactory performance against standard industry tests. Two such industry tests are the ISOT and the L60-1. However, boron imparts certain undesirable properties to the lubricant such as moisture sensitivity and increased price. Thus, it is desirable to have a lubricant that can provide the performance demanded by industry while reducing or eliminating the presence of boron. Recently, a boron-free lubricant additive package has been developed that unexpectedly passes both the ISOT standard test and the L60-1 standard test.
  • the present invention provides a lubricating additive package that is capable of passing both the ISOT standard test and the L60-1 standard test. More specifically, the present invention in an embodiment provides an oil soluble lubricant additive package comprising: (a) a succinimide dispersant, (b) an antiwear agent, (c) an extreme pressure additive, wherein the weight ratio of said dispersant to said extreme pressure additive is from about 1:7 to about 1:2, and wherein the package is boron-free, and wherein the total phosphorus content of the package is not more than about 500 ppm.
  • a lubricating oil comprising: (a) a base oil; and (b) the oil soluble lubricant additive package taught herein.
  • the base oils useful herein include natural lubricating oils, synthetic lubricating oils, and mixtures thereof. Suitable lubricating oils also include basestocks obtained by isomerization of synthetic wax and slack wax, as well as basestocks produced by hydrocracking the aromatic and polar components of the crude. In general, both the natural and synthetic lubricating oils will each have a kinematic viscosity ranging from about 1 to about 40 mm 2 /s (cSt) at 100° C., although typical applications will require each of the base oils to have a viscosity ranging from about 1 to about 16 mm 2 /s (cSt) at 100° C., preferably 2 to 15 mm 2 /s (cSt) at 100° C. Natural lubricating oils include animal oils, vegetable oils (e.g., castor oil and lard oil), petroleum oils, mineral oils, and oils derived from coal or shale. The preferred natural lubricating oil comprises mineral oil.
  • the mineral oils useful in this invention can include but are not limited to all common mineral oil base stocks. This would include oils that are naphthenic or paraffinic in chemical structure. Oils that are refined by conventional methodology using acid, alkali, and clay or other agents such as aluminum chloride, or be extracted oils produced, for example, by solvent extraction with solvents such as phenol, sulfur dioxide, furfural, dichlorodiethyl ether, etc. They may be hydrotreated or hydrorefined, dewaxed by chilling or catalytic dewaxing processes, or hydrocracked. The mineral oil may be produced from natural crude sources or be composed of isomerized wax materials or residues of other refining processes.
  • the oil of lubricating viscosity is a hydrotreated, hydrocracked and/or iso-dewaxed mineral oil having a Viscosity Index (VI) of greater than 80, preferably greater than 90; greater than 90 volume % saturates and less than 0.03 wt. % sulfur.
  • VI Viscosity Index
  • Group II and Group III basestocks are also particularly suitable for use in the present invention, and are typically prepared from conventional feedstocks using a severe hydrogenation step to reduce the aromatic, sulfur and nitrogen content, followed by dewaxing, hydrofinishing, extraction and/or distillation steps to produce the finished base oil.
  • base oils known as Group III, ⁇ 0.03 wt. % sulfur, and ⁇ 90 vol % saturates, viscosity index >120; and Group IV, poly-alpha-olefins. Hydrotreated basestocks and catalytically dewaxed basestocks, because of their low sulfur and aromatics content, generally fall into the Group II and Group III categories.
  • the base oil comprises a mineral oil having a VI of at least 110.
  • the lubricating oils may be derived from refined, re-refined oils, or mixtures thereof.
  • Unrefined oils are obtained directly from a natural source or synthetic source (e.g., coal, shale, or tar sands bitumen) without further purification or treatment.
  • Examples of unrefined oils include shale oil obtained directly from a retorting operation, petroleum oil obtained directly from distillation, or an ester oil obtained directly from an esterification process, each of which is then used without further treatment.
  • Refined oils are similar to the unrefined oils except that refined oils have been treated in one or more purification steps to improve one or more properties.
  • Suitable purification techniques include distillation, hydrotreating, dewaxing, solvent extraction, acid or base extraction, filtration, and percolation, all of which are known to those skilled in the art.
  • Re-refined oils are obtained by treating used oils in processes similar to those used to obtain the refined oils. These re-refined oils are also known as reclaimed or reprocessed oils and are often additionally processed by techniques for removal of spent additives and oil breakdown products.
  • Synthetic lubricating oils include hydrocarbon oils and halo-substituted hydrocarbon oils such as oligomerized, polymerized, and interpolymerized olefins; alkylbenzenes; polyphenyls; and alkylated diphenyl ethers, alkylated diphenyl sulfides, as well as their derivatives, analogs, and homologs thereof, and the like.
  • Preferred synthetic oils are oligomers of ⁇ -olefins, particularly oligomers of 1-decene, having a viscosity ranging from about 1 to about 12, preferably 2 to 8, mm 2 /s (cSt) at 100° C. These oligomers are known as poly- ⁇ -olefins or PAOs.
  • Synthetic lubricating oils also include alkylene oxide polymers, interpolymers, copolymers, and derivatives thereof where the terminal hydroxyl groups have been modified by esterification, etherification, etc.
  • This class of synthetic oils is exemplified by polyoxyalkylene polymers prepared by 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 1000, diphenyl ether of polypropylene glycol having a molecular weight of 100-1500); and mono- and poly-carboxylic esters thereof (e.g., the acetic acid esters, mixed C 3 -C 8 fatty acid esters, and C 12 oxo acid diester of tetraethylene glycol).
  • Another suitable class of synthetic lubricating oils comprises the esters of dicarboxylic acids (e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, subric acid, sebasic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkylmalonic 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 monoethers, propylene glycol, etc.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids and alkenyl succinic acids, maleic acid, azelaic acid, subric acid, sebasic acid, fumaric acid, adipic acid,
  • esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl isothalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebasic acid with two moles of tetraethylene glycol and two moles of 2-ethyl-hexanoic acid, and the like.
  • a preferred type of oil from this class of synthetic oils is adipates of C 4 to C 12 alcohols.
  • Esters useful as synthetic lubricating oils also include those made from C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylolpropane pentaeythritol, dipentaerythritol, tripentaerythritol, and the like.
  • Silicon-based oils (such as the polyalkyl-, polyaryl-, polyalkoxy-, or polyaryloxy-siloxane oils and silicate oils) comprise another useful class of synthetic lubricating oils. These oils include tetra-ethyl silicate, tetra-isopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-ethylhexyl) silicate, tetra-(p-tert-butylphenyl) silicate, hexa-(4-methyl-2-pentoxy)-disiloxane, poly(methyl)-siloxanes and poly (methylphenyl) siloxanes, and the like.
  • oils include tetra-ethyl silicate, tetra-isopropyl silicate, tetra-(2-ethylhexyl) silicate, tetra-(4-methyl-2-
  • Other synthetic lubricating oils include liquid esters of phosphorus containing acids (e.g., tricresyl phosphate, trioctylphosphate, and diethyl ester of decylphosphonic acid), polymeric tetra-hydrofurans, poly-alpha-olefins, and the like.
  • liquid esters of phosphorus containing acids e.g., tricresyl phosphate, trioctylphosphate, and diethyl ester of decylphosphonic acid
  • polymeric tetra-hydrofurans e.g., polymeric tetra-hydrofurans, poly-alpha-olefins, and the like.
  • Dispersants derived from polyisobutylene (PIB) or mixed butane-substituted succinimides are among the succinimide dispersants useful herein, where the molecular weight range of the PIB is approximately 900-2100, most especially MW range 1200-1500.
  • the succinimide is malienated to a succinic anhydride to PIB ratio of approximately 1.0-1.25.
  • the polyisobutylene succinic anhydride intermediate can be further reacted with a suitable amine including any mono-, di-, or polyamine.
  • the dispersant may comprise one or more of various types of ashless dispersants including succinimides, succinamides, succinic esters, and succinic ester-amides.
  • the ashless dispersant may comprise one or more alkenyl succinimides of an amine having at least one primary amino group capable of forming an imide group.
  • the alkenyl succinimides may 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 may be made readily by heating a mixture of polyolefin and maleic anhydride to about 180°-220° C.
  • the polyolefin may 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 700 to about 2100 as determined by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • Amines which may be employed in forming the ashless dispersant include without limitation 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, N-phenylenediamine, and the like.
  • Suitable amines may 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 may be an integer from about one to about ten. These include: ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, and the like, including mixtures thereof in which case n is the average value of the mixture.
  • ethylene polyamines have a primary amine group at each end so they may form mono-alkenylsuccinimides and bis-alkenylsuccinimides.
  • Commercially available ethylene polyamine mixtures may 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 may 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 may be from about 1:1 to about 2.4:1.
  • the ashless dispersant may comprise 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
  • the dispersant may contain at least one polyalkylene moiety.
  • the dispersant may comprise at least two polyalkylene moieties.
  • the polyalkylene moiety may have a molecular weight of from about 900 amu to about 3000 amu.
  • the polyalkylene moiety polyalkylene moiety may, for example, have a molecular weight of from about 1300 amu to about 2100 amu.
  • the polyalkylene moiety may have a molecular weight of about 2100 amu.
  • the polyalkylene moiety may comprise a polybutenyl group.
  • the dispersant may 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.
  • the dispersant may be further reacted with an organic acid, an anhydride, and/or an aldehyde/phenol mixture. Such a process may enhance compatibility with elastomer seals, for example.
  • the dispersant may further comprise a mixture of dispersants.
  • the dispersant may comprise nitrogen and/or may be free of phosphorus.
  • the dispersant may be present in an embodiment in the lubricating fluid in an amount of about 1 wt % to about 5 wt %.
  • the dispersant used in some embodiments of the present disclosure may comprise a succinimide prepared from an alkenyl succinic acid or anhydride and ammonia.
  • the succinimide may comprise the reaction product of a succinic anhydride and ammonia.
  • the alkenyl group of the alkenyl succinic acid may be a short chain alkenyl group, for example, the alkenyl group may comprise about 12 to about 36 carbon atoms.
  • the succinic anhydride may comprise a C 12 to about C 36 aliphatic hydrocarbyl succinimide.
  • the succinic anhydride may comprise a C 16 to about C 28 aliphatic hydrocarbyl succinimide.
  • the succinic anhydride may comprise a C 18 to about C 24 aliphatic hydrocarbyl succinimide.
  • the succinimide may be prepared from a succinic anhydride and ammonia as described in European Patent 0 020 037, herein incorporated by reference. Further, the succinimide may comprise HiTEC® 3191 friction modifier, available from Ethyl Corporation. In some embodiments, no non-metallic friction modifier other than the succinimide disclosed herein is included.
  • the succinimide may comprise one or more of a compound having the following structure: wherein Z may have the structure:
  • One embodiment utilizes a poly-amine of the type tetra ethyl pentamine.
  • examples can include but are not limited to HiTEC® 646 Dispersant, available from Ethyl Corporation, and similar succinimide dispersants.
  • Extreme pressure agents known to those skilled in the art are useful in the lubricant additive packages, lubricating oil, lubricated machines, and methods of the present invention. Also useful herein as extreme pressure agents are sulfurized olefins, including but not limited to sulfurized isobutylene, alkylpolysulfides and sulfurized fatty acid esters.
  • Corrosion inhibitors of the thiadiazole and triazole classes are suitable for use in this invention.
  • Alkyl substituted thiadiazoles as well as alkyl substituted triazoles are useful in this invention.
  • Antiwear and siloxane-containing polymer antifoam agents can also be employed in the lubricant additive packages and finished lubricating oils of the present invention.
  • a variety of oil-soluble sulphur-containing antiwear and/or extreme pressure additives can be used in the practice of this invention. Examples are included within the categories of dihydrocarbyl polysulphides; sulphurized olefins; sulphurized fatty acid esters of both natural and synthetic origins; trithiones; sulphurized thienyl derivatives; sulphurized terpenes; sulphurized oligomers of C 2 -C 8 monoolefins; and sulphurized Dieis-Alder adducts such as those disclosed in U.S. reissue patent Re 27,331.
  • Specific examples include sulphurized polyisobutene of Mn 1,100, sulfurized isobutylene, sulphurized diisobutylene, sulphurized triisobutylene, dicyclohexyl polysulphide, diphenyl polysulphide, dibenzyl polysulphide, dinonyl polysulphide, and mixtures of di-tert-butyl polysulphide such as mixtures of di-tert-butyl trisulphide, di-tert-butyl tetrasulphide and di-tert-butyl pentasulphide, among others.
  • Combinations of such categories of sulphur-containing antiwear and/or extreme pressure agents can also be used, such as a combination of sulphurized isobutylene and di-tert-butyl trisulphide, a combination of sulphurized isobutylene and dinonyl trisulphide, a combination of sulphurized tall oil and dibenzyl polysulphide, and the like.
  • a component which contains both phosphorus and sulphur in its chemical structure is deemed a phosphorus-containing antiwear and/or extreme pressure agent rather than a sulphur-containing antiwear and/or extreme pressure agent.
  • phosphorus- and nitrogen-containing antiwear and/or extreme pressure additives which can be employed in the practice of this invention are the phosphorus- and nitrogen-containing compositions of the type described in G.B. 1,009,913; G.B. 1,009,914; U.S. Pat. No. 3,197,405 and/or U.S. Pat. No. 3,197,496.
  • compositions are formed by forming an acidic intermediate by the reaction of a hydroxy-substituted triester of a phosphorothioic acid with an inorganic phosphorus acid, phosphorus oxide or phosphorus halide, and neutralizing a substantial portion of said acidic intermediate with an amine or hydroxy-substituted amine.
  • Another type of phosphorus- and nitrogen-containing antiwear and/or extreme pressure additive which can be used in the compositions of this invention is the amine salts of hydroxy-substituted phosphetanes or the amine salts of hydroxy-substituted thiophosphetanes.
  • this general type of antiwear and/or extreme pressure agent include the amine salts hydroxyphosphetanes and the amine salts of hydroxy-thiophosphetanes typified by Irgalube 295 additive (Ciba-Geigy Corporation).
  • Another useful category of phosphorus- and nitrogen-containing antiwear and/or extreme pressure agents is comprised of the amine salts of partial esters of phosphoric and thiophosphoric acids.
  • EP 531 585 referred to above.
  • the formulations of the present invention have a total phosphorus content of not more than about 500 ppm.
  • the formulations are also boron-free.
  • boron-free herein is meant substantially free of boron whereby trace amounts of or contamination with low or unintended levels of boron are to be included.
  • Boron-free can herein include low levels of boron up to about 25 ppm.
  • substantially free of boron herein is meant less than about 50 ppm of boron.
  • An example of an oil soluble lubricant additive package formulation of the present invention is outlined in the table below: COmponent Wt % Sulfurized olefin 30-50 Primary amine 0.1-5 Acid phosphate 0.5-5.0 Rust Inhibitor 0.01-1 Antifoamant 0.2-2.0 Corrosion Inhibitor 0.2-2.0 Diluent Oil 30-40 Dispersant 2-15.0
  • a finished oil comprising the preferred boron-free oil soluble lubricant additive package was manufactured for testing purposes.
  • the finished oil was then tested by the L60-1 and the ISOT standard tests. It was unexpected that a lubricant additive package could pass both the L60-1 and ISOT standard tests without the inclusion of a boron source in the formulation.
  • the L60-1 test requires at least a 7.5 carbon/varnish (C/V) rating or higher to pass, and at least a 9.4 sludge rating or higher to pass.
  • the L60-1 rating is based on a merit system with 10 indicating no carbon/varnish and zero representing the worst rating.
  • the ISOT test conversely, requires at most a 3.0 for varnish on the glass beaker and for varnish on the glass rod to indicate clean gear performance.
  • the ISOT rating is based on a demerit system with the best ISOT rating zero indicating no varnish and 9 representing the worst varnish rating. This rating may also be described as thinly to lightly adhering lacquer in the ISOT procedure. Note that prior art formulations containing phosphorus and boron pass both tests. Formulations with low phosphorus alone do not pass both tests. Only the formulations of the present invention with both low phosphorus and a dispersant pass both tests without boron.
  • the formulations of the present invention are especially effective in the lubrication of vehicular axle gears and vehicular transmission gears.
  • the vehicles can be passenger cars, light duty trucks, heavy duty trucks, buses, recreation vehicles, marine craft, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
US10/670,580 2003-09-25 2003-09-25 Boron free automotive gear oil Abandoned US20050070446A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US10/670,580 US20050070446A1 (en) 2003-09-25 2003-09-25 Boron free automotive gear oil
CA002480114A CA2480114A1 (en) 2003-09-25 2004-09-03 Boron free automotive gear oil
AU2004210592A AU2004210592A1 (en) 2003-09-25 2004-09-10 Boron free automotive gear oil
EP04077548A EP1518919A1 (en) 2003-09-25 2004-09-15 Boron free automotive gear oil
JP2004272174A JP2005097615A (ja) 2003-09-25 2004-09-17 ホウ素を含まない自動車用ギヤー油
MXPA04009160A MXPA04009160A (es) 2003-09-25 2004-09-21 Aceite automotriz para engranajes libre de boro.
SG200405365A SG110161A1 (en) 2003-09-25 2004-09-24 Boron free automotive gear oil
US11/552,733 US20070054813A1 (en) 2003-09-25 2006-10-25 Boron free automotive gear oil
JP2011270247A JP2012046769A (ja) 2003-09-25 2011-12-09 ホウ素を含まない油溶性潤滑剤用添加剤パッケージ

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US10/670,580 US20050070446A1 (en) 2003-09-25 2003-09-25 Boron free automotive gear oil

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/552,733 Continuation US20070054813A1 (en) 2003-09-25 2006-10-25 Boron free automotive gear oil

Publications (1)

Publication Number Publication Date
US20050070446A1 true US20050070446A1 (en) 2005-03-31

Family

ID=34194829

Family Applications (2)

Application Number Title Priority Date Filing Date
US10/670,580 Abandoned US20050070446A1 (en) 2003-09-25 2003-09-25 Boron free automotive gear oil
US11/552,733 Abandoned US20070054813A1 (en) 2003-09-25 2006-10-25 Boron free automotive gear oil

Family Applications After (1)

Application Number Title Priority Date Filing Date
US11/552,733 Abandoned US20070054813A1 (en) 2003-09-25 2006-10-25 Boron free automotive gear oil

Country Status (7)

Country Link
US (2) US20050070446A1 (ja)
EP (1) EP1518919A1 (ja)
JP (2) JP2005097615A (ja)
AU (1) AU2004210592A1 (ja)
CA (1) CA2480114A1 (ja)
MX (1) MXPA04009160A (ja)
SG (1) SG110161A1 (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040214729A1 (en) * 2003-04-25 2004-10-28 Buitrago Juan A. Gear oil composition having improved copper corrosion properties
US20230167380A1 (en) * 2020-05-05 2023-06-01 Totalenergies Onetech Lubricating composition for electric vehicles

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070078066A1 (en) * 2005-10-03 2007-04-05 Milner Jeffrey L Lubricant formulations containing extreme pressure agents
US8003584B2 (en) 2006-07-14 2011-08-23 Afton Chemical Corporation Lubricant compositions
US7902133B2 (en) 2006-07-14 2011-03-08 Afton Chemical Corporation Lubricant composition
US7906465B2 (en) 2006-07-14 2011-03-15 Afton Chemical Corp. Lubricant compositions
US20080015127A1 (en) * 2006-07-14 2008-01-17 Loper John T Boundary friction reducing lubricating composition
US7879775B2 (en) 2006-07-14 2011-02-01 Afton Chemical Corporation Lubricant compositions
US10233905B2 (en) 2011-10-28 2019-03-19 Rem Technologies, Inc. Wind turbine gearbox lubrication system
CA3150270A1 (en) * 2019-08-16 2021-02-25 The Lubrizol Corporation Composition and method for lubricating automotive gears, axles and bearings

Citations (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459112A (en) * 1945-07-06 1949-01-11 Socony Vacuum Oil Co Inc Mineral oil composition
US2675366A (en) * 1951-05-24 1954-04-13 American Cyanamid Co Stabilization of polyethylene
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
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
US3197405A (en) * 1962-07-09 1965-07-27 Lubrizol Corp Phosphorus-and nitrogen-containing compositions and process for preparing the same
US3197496A (en) * 1961-08-09 1965-07-27 Lubrizol Corp Polyphosphorus ester derivatives of o, o-dihydrocarbyl-s-hydroxylalkyl phosphorodithioates
US3202678A (en) * 1959-08-24 1965-08-24 California Research Corp Alkenyl succinimides of tetraethylene pentamine
US3236770A (en) * 1960-09-28 1966-02-22 Sinclair Research Inc Transaxle lubricant
US3238263A (en) * 1962-12-31 1966-03-01 Exxon Research Engineering Co Calcium salts of bridged phenols
US3254025A (en) * 1961-08-18 1966-05-31 Lubrizol Corp Boron-containing acylated amine and lubricating compositions 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
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
US3331776A (en) * 1962-10-04 1967-07-18 Shell Oil Co Lubricating oil composition
US3368972A (en) * 1965-01-06 1968-02-13 Mobil Oil Corp High molecular weight mannich bases as engine oil additives
US3372116A (en) * 1965-10-05 1968-03-05 Lubrizol Corp Preparation of basic metal phenates and salicylates
US3381022A (en) * 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
USRE26433E (en) * 1963-12-11 1968-08-06 Amide and imide derivatives of metal salts of substituted succinic acids
US3399141A (en) * 1966-02-09 1968-08-27 Rohm & Haas Heterocyclic esters of alkenylsuccinic anhydrides
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
US3451933A (en) * 1967-08-11 1969-06-24 Rohm & Haas Formamido-containing alkenylsuccinates
US3454555A (en) * 1965-01-28 1969-07-08 Shell Oil Co Oil-soluble halogen-containing polyamines and polyethyleneimines
US3454497A (en) * 1966-11-14 1969-07-08 Shell Oil Co Lubricating compositions
US3454607A (en) * 1969-02-10 1969-07-08 Lubrizol Corp High molecular weight carboxylic compositions
US3459661A (en) * 1967-01-20 1969-08-05 Shell Oil Co Lubricating compositions containing metal salts of particular condensation products
US3461172A (en) * 1966-11-22 1969-08-12 Consolidation Coal Co Hydrogenation of ortho-phenolic mannich bases
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
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
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
US3591598A (en) * 1968-11-08 1971-07-06 Standard Oil Co Certain condensation products derived from mannich bases
US3600372A (en) * 1968-06-04 1971-08-17 Standard Oil Co Carbon disulfide treated mannich condensation products
US3632511A (en) * 1969-11-10 1972-01-04 Lubrizol Corp Acylated nitrogen-containing compositions processes for their preparationand 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
USRE27331E (en) * 1966-12-19 1972-04-11 Sulfurized diels-alder adducts and lubricants containing the same
US3657133A (en) * 1967-12-27 1972-04-18 Shell Oil Co Preservative for elastomers
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
US3725480A (en) * 1968-11-08 1973-04-03 Standard Oil Co Ashless oil additives
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
US3751365A (en) * 1965-10-22 1973-08-07 Standard Oil Co Concentrates and crankcase oils comprising oil solutions of boron containing high molecular weight mannich reaction condensation products
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
US3798165A (en) * 1965-10-22 1974-03-19 Standard Oil Co Lubricating oils containing high molecular weight mannich condensation products
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
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
US3865739A (en) * 1974-02-25 1975-02-11 Texaco Inc Thiadiazole derivative, mixture and compositions thereof
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
US3957855A (en) * 1971-06-11 1976-05-18 The Lubrizol Corporation Ester-containing compositions
US3957854A (en) * 1971-06-11 1976-05-18 The Lubrizol Corporation Ester-containing compositions
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
US4087469A (en) * 1975-12-16 1978-05-02 Yakov Abramovich Gurvich Method of producing 2,2 '-methylenebis(4,6-dialkylphenols)
US4284520A (en) * 1979-05-15 1981-08-18 Institut National De Recherche Chimique Appliquee Stable and non-corrosive polysulphides derived from olefins and having different sulphur contents, process for their manufacture and applications thereof
US4492713A (en) * 1982-09-24 1985-01-08 Chauvin John A Method of automatic roux making
US4747690A (en) * 1985-10-29 1988-05-31 Rheon Automatic Machinery Co., Ltd. Kneading apparatus for bread dough and the like and a method of controlling the quality thereof during kneading
US4800032A (en) * 1987-07-08 1989-01-24 The Lubrizol Corporation Aliphatic hydrocarbon substituted aromatic hydrocarbons to control black sludge in lubricants
US5082470A (en) * 1987-10-08 1992-01-21 Exxon Chemical Patents Inc. Alkyl phenol-formaldehyde condensates as fuel additives
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5114601A (en) * 1990-03-31 1992-05-19 Bp Chemicals (Additive) Limited Overbased calixarates, compositions containing them and use as lubricating oil additives
US5126064A (en) * 1989-05-22 1992-06-30 Ethyl Petroleum Additives, Ltd. Lubricant compositions
US5176840A (en) * 1990-02-16 1993-01-05 Ethyl Petroleum Additives, Inc. Gear oil additive composition and gear oil containing the same
US5205946A (en) * 1990-03-31 1993-04-27 Bp Chemicals (Additives) Limited Process for the production of overbased calixarates
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
US5330665A (en) * 1982-05-22 1994-07-19 Bp Chemicals (Additives) Limited Production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
US5411711A (en) * 1990-07-30 1995-05-02 Emitec Gesellschaft Fuer Emissionstechnologie Mbh Electrically heatable honeycomb body, in particular catalyst carrier body, with internal support structures
US5492638A (en) * 1993-03-16 1996-02-20 Ethyl Petroleum Additives Limited Gear oil lubricants of enhanced friction properties
US5620948A (en) * 1995-05-18 1997-04-15 The Lubrizol Corporation Additive combinations for lubricants and functional fluids
US5629272A (en) * 1991-08-09 1997-05-13 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
US5763372A (en) * 1996-12-13 1998-06-09 Ethyl Corporation Clean gear boron-free gear additive and method for producing same
US5922656A (en) * 1997-03-24 1999-07-13 Tonen Corporation Lubricant compositions for automatic transmissions
US6248142B1 (en) * 1996-10-11 2001-06-19 Exxon Chemical Patents Inc Fuel composition containing lubricity additive
US20030004070A1 (en) * 2001-06-15 2003-01-02 Keith Strickland Gas-fuelled engine lubricating oil compositions
US6559105B2 (en) * 2000-04-03 2003-05-06 The Lubrizol Corporation Lubricant compositions containing ester-substituted hindered phenol antioxidants
US6569818B2 (en) * 2000-06-02 2003-05-27 Chevron Oronite Company, Llc Lubricating oil composition
US6593281B2 (en) * 2000-06-05 2003-07-15 Tonengeneral Sekiyu K.K. Lubricating oil composition for automatic transmission
US6673751B1 (en) * 2002-11-06 2004-01-06 The Lubrizol Corporation Boron containing overbased calixarates and lubricants and methods thereof
US6720293B2 (en) * 2000-09-25 2004-04-13 Infineum International Ltd. Low viscosity lubricating oil compositions
US20040102335A1 (en) * 2002-11-25 2004-05-27 The Lubrizol Corporation Additive formulation for lubricating oils
US6764982B2 (en) * 2001-02-07 2004-07-20 The Lubrizol Corporation Lubricating oil composition

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2962442A (en) * 1957-01-03 1960-11-29 Socony Mobil Oil Co Inc Preparation of aldehyde-polyamine-hydroxyaromatic compound condensates and hydrocarbon fractions containing the same
US3215707A (en) * 1960-06-07 1965-11-02 Lubrizol Corp Lubricant
US3355270A (en) * 1963-06-03 1967-11-28 Standard Oil Co Metal chelate combustion improver for fuel oil
NL137371C (ja) * 1963-08-02
US3415750A (en) * 1963-10-04 1968-12-10 Monsanto Co Imidazolines having polyalkenylsuccinimido-containing substituents
US3346493A (en) * 1963-12-26 1967-10-10 Lubrizol Corp Lubricants containing metal complexes of alkenyl succinic acid-amine reaction product
US3216936A (en) * 1964-03-02 1965-11-09 Lubrizol Corp Process of preparing lubricant additives
GB1052380A (ja) * 1964-09-08
US3281357A (en) * 1964-12-02 1966-10-25 Lubrizol Corp Process for preparing nitrogen and aluminum containing compositions
DE1595234A1 (de) * 1965-04-27 1970-03-05 Roehm & Haas Gmbh Verfahren zur Herstellung oligomerer bzw. polymerer Amine
US3340281A (en) * 1965-06-14 1967-09-05 Standard Oil Co Method for producing lubricating oil additives
US3704308A (en) * 1965-10-22 1972-11-28 Standard Oil Co Boron-containing high molecular weight mannich condensation
US3697574A (en) * 1965-10-22 1972-10-10 Standard Oil Co Boron derivatives of high molecular weight mannich condensation products
US3756953A (en) * 1965-10-22 1973-09-04 Standard Oil Co Vatives of high molecular weight mannich reaction condensation concentrate and crankcase oils comprising oil solutions of boron deri
US3539633A (en) * 1965-10-22 1970-11-10 Standard Oil Co Di-hydroxybenzyl polyamines
US3272746A (en) * 1965-11-22 1966-09-13 Lubrizol Corp Lubricating composition containing an acylated nitrogen compound
US3703536A (en) * 1967-11-24 1972-11-21 Standard Oil Co Preparation of oil-soluble boron derivatives of an alkylene polyamine-substituted phenol-formaldehyde addition product
US3541012A (en) * 1968-04-15 1970-11-17 Lubrizol Corp Lubricants and fuels containing improved acylated nitrogen additives
GB1282887A (en) * 1968-07-03 1972-07-26 Lubrizol Corp Acylation of nitrogen-containing products
US3543678A (en) * 1968-10-21 1970-12-01 Sperry Rand Corp Feeder mechanism for a baling machine
FR2044708B1 (ja) * 1969-04-01 1974-07-12 Lubrizol Corp
US3991098A (en) * 1971-11-30 1976-11-09 Toa Nenryo Kogyo Kabushiki Kaisha Lubricating oil additive, process for the synthesis thereof and lubricating oil additive composition
US3836471A (en) * 1973-05-14 1974-09-17 Lubrizol Corp Lubricants and fuels containing ester-containing compositions
US3980569A (en) * 1974-03-15 1976-09-14 The Lubrizol Corporation Dispersants and process for their preparation
US4173540A (en) * 1977-10-03 1979-11-06 Exxon Research & Engineering Co. Lubricating oil composition containing a dispersing-varnish inhibiting combination of polyol ester compound and a borated acyl nitrogen compound
US4234435A (en) * 1979-02-23 1980-11-18 The Lubrizol Corporation Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation
US4654156A (en) * 1985-09-12 1987-03-31 Mobil Oil Corporation Sulfurized olefins as antiwear additives and compositions thereof
EP0373454A1 (en) * 1988-12-08 1990-06-20 Idemitsu Kosan Company Limited Lubricating oil composition for power control
JP2705815B2 (ja) * 1988-12-08 1998-01-28 出光興産株式会社 動力制御用潤滑油組成物
JP2824070B2 (ja) * 1988-12-08 1998-11-11 出光興産株式会社 ギヤ油組成物
CA2028399C (en) * 1989-11-13 2000-08-29 Stephen Norman Gear oils and additives therefor
EP0531585B1 (en) 1991-09-09 1998-11-04 Ethyl Petroleum Additives Limited Oil additive concentrates and lubricants of enhanced performance capabilities
WO1994004637A1 (en) * 1992-08-18 1994-03-03 Ethyl Japan Corporation Lubricating oil composition for wet clutch or wet brake
US5851962A (en) * 1992-08-18 1998-12-22 Ethyl Japan Corporation Lubricant composition for wet clutch or wet brake
JP4354014B2 (ja) * 1995-10-05 2009-10-28 出光興産株式会社 無段変速機用潤滑油組成物
US5843874A (en) * 1996-06-12 1998-12-01 Ethyl Corporation Clean performing gear oils
JP3970354B2 (ja) * 1996-06-25 2007-09-05 出光興産株式会社 無段変速機用潤滑油組成物
JP2001139976A (ja) * 1999-11-10 2001-05-22 Yushiro Chem Ind Co Ltd 金属加工用潤滑油組成物

Patent Citations (99)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459112A (en) * 1945-07-06 1949-01-11 Socony Vacuum Oil Co Inc Mineral oil composition
US2675366A (en) * 1951-05-24 1954-04-13 American Cyanamid Co Stabilization of polyethylene
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
US3202678A (en) * 1959-08-24 1965-08-24 California Research Corp Alkenyl succinimides of tetraethylene pentamine
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
US3197496A (en) * 1961-08-09 1965-07-27 Lubrizol Corp Polyphosphorus ester derivatives of o, o-dihydrocarbyl-s-hydroxylalkyl phosphorodithioates
US3254025A (en) * 1961-08-18 1966-05-31 Lubrizol Corp Boron-containing acylated amine and lubricating compositions containing the same
US3197405A (en) * 1962-07-09 1965-07-27 Lubrizol Corp Phosphorus-and nitrogen-containing compositions and process for preparing the same
US3184474A (en) * 1962-09-05 1965-05-18 Exxon Research Engineering Co Reaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial
US3331776A (en) * 1962-10-04 1967-07-18 Shell Oil Co Lubricating oil composition
US3238263A (en) * 1962-12-31 1966-03-01 Exxon Research Engineering Co Calcium salts of bridged phenols
US3522179A (en) * 1963-04-23 1970-07-28 Lubrizol Corp Lubricating composition containing esters of hydrocarbon-substituted succinic acid
US3632510A (en) * 1963-04-23 1972-01-04 Lubrizol Corp Mixed ester-metal salts and lubricants and fuels containing the same
US3381022A (en) * 1963-04-23 1968-04-30 Lubrizol Corp Polymerized olefin substituted succinic acid esters
USRE26433E (en) * 1963-12-11 1968-08-06 Amide and imide derivatives of metal salts of substituted succinic acids
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
US3454555A (en) * 1965-01-28 1969-07-08 Shell Oil Co Oil-soluble halogen-containing polyamines and polyethyleneimines
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
US3372116A (en) * 1965-10-05 1968-03-05 Lubrizol Corp Preparation of basic metal phenates and salicylates
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
US3751365A (en) * 1965-10-22 1973-08-07 Standard Oil Co Concentrates and crankcase oils comprising oil solutions of boron containing high molecular weight mannich reaction condensation products
US3798165A (en) * 1965-10-22 1974-03-19 Standard Oil Co Lubricating oils containing high molecular weight mannich condensation products
US3725277A (en) * 1966-01-26 1973-04-03 Ethyl Corp Lubricant compositions
US3399141A (en) * 1966-02-09 1968-08-27 Rohm & Haas Heterocyclic esters of alkenylsuccinic anhydrides
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
US3454497A (en) * 1966-11-14 1969-07-08 Shell Oil Co Lubricating compositions
US3461172A (en) * 1966-11-22 1969-08-12 Consolidation Coal Co Hydrogenation of ortho-phenolic mannich bases
USRE27331E (en) * 1966-12-19 1972-04-11 Sulfurized diels-alder adducts and lubricants containing the same
US3459661A (en) * 1967-01-20 1969-08-05 Shell Oil Co Lubricating compositions containing metal salts of particular condensation products
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
US3448049A (en) * 1967-09-22 1969-06-03 Rohm & Haas Polyolefinic succinates
US3657133A (en) * 1967-12-27 1972-04-18 Shell Oil Co Preservative for elastomers
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
US3600372A (en) * 1968-06-04 1971-08-17 Standard Oil Co Carbon disulfide treated mannich condensation products
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
US3634515A (en) * 1968-11-08 1972-01-11 Standard Oil Co Alkylene polyamide formaldehyde
US3591598A (en) * 1968-11-08 1971-07-06 Standard Oil Co Certain condensation products derived from mannich bases
US3725480A (en) * 1968-11-08 1973-04-03 Standard Oil Co Ashless oil additives
US3726882A (en) * 1968-11-08 1973-04-10 Standard Oil Co Ashless oil additives
US3454607A (en) * 1969-02-10 1969-07-08 Lubrizol Corp High molecular weight carboxylic compositions
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
US3803039A (en) * 1970-07-13 1974-04-09 Standard Oil Co Oil solution of aliphatic acid derivatives of high molecular weight mannich condensation product
US3798247A (en) * 1970-07-13 1974-03-19 Standard Oil Co Oil soluble aliphatic acid derivatives of molecular weight mannich condensation products
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
US3936480A (en) * 1971-07-08 1976-02-03 Rhone-Progil Additives for improving the dispersing properties of lubricating oil
US3862981A (en) * 1971-07-08 1975-01-28 Rhone Progil New lubricating oil additives
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
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
US3865739A (en) * 1974-02-25 1975-02-11 Texaco Inc Thiadiazole derivative, mixture and compositions thereof
US4087469A (en) * 1975-12-16 1978-05-02 Yakov Abramovich Gurvich Method of producing 2,2 '-methylenebis(4,6-dialkylphenols)
US4284520A (en) * 1979-05-15 1981-08-18 Institut National De Recherche Chimique Appliquee Stable and non-corrosive polysulphides derived from olefins and having different sulphur contents, process for their manufacture and applications thereof
US5330665A (en) * 1982-05-22 1994-07-19 Bp Chemicals (Additives) Limited Production of either an alkaline earth metal alkyl phenate or a sulphurised alkaline earth metal alkyl phenate
US4492713A (en) * 1982-09-24 1985-01-08 Chauvin John A Method of automatic roux making
US4747690A (en) * 1985-10-29 1988-05-31 Rheon Automatic Machinery Co., Ltd. Kneading apparatus for bread dough and the like and a method of controlling the quality thereof during kneading
US4800032A (en) * 1987-07-08 1989-01-24 The Lubrizol Corporation Aliphatic hydrocarbon substituted aromatic hydrocarbons to control black sludge in lubricants
US5102566A (en) * 1987-10-02 1992-04-07 Exxon Chemical Patents Inc. Low ash lubricant compositions for internal combustion engines (pt-727)
US5082470A (en) * 1987-10-08 1992-01-21 Exxon Chemical Patents Inc. Alkyl phenol-formaldehyde condensates as fuel additives
US5126064A (en) * 1989-05-22 1992-06-30 Ethyl Petroleum Additives, Ltd. Lubricant compositions
US5176840A (en) * 1990-02-16 1993-01-05 Ethyl Petroleum Additives, Inc. Gear oil additive composition and gear oil containing the same
US5225093A (en) * 1990-02-16 1993-07-06 Ethyl Petroleum Additives, Inc. Gear oil additive compositions and gear oils containing the same
US5114601A (en) * 1990-03-31 1992-05-19 Bp Chemicals (Additive) Limited Overbased calixarates, compositions containing them and use as lubricating oil additives
US5205946A (en) * 1990-03-31 1993-04-27 Bp Chemicals (Additives) Limited Process for the production of overbased calixarates
US5411711A (en) * 1990-07-30 1995-05-02 Emitec Gesellschaft Fuer Emissionstechnologie Mbh Electrically heatable honeycomb body, in particular catalyst carrier body, with internal support structures
US5629272A (en) * 1991-08-09 1997-05-13 Oronite Japan Limited Low phosphorous engine oil compositions and additive compositions
US5492638A (en) * 1993-03-16 1996-02-20 Ethyl Petroleum Additives Limited Gear oil lubricants of enhanced friction properties
US5620948A (en) * 1995-05-18 1997-04-15 The Lubrizol Corporation Additive combinations for lubricants and functional fluids
US6248142B1 (en) * 1996-10-11 2001-06-19 Exxon Chemical Patents Inc Fuel composition containing lubricity additive
US5763372A (en) * 1996-12-13 1998-06-09 Ethyl Corporation Clean gear boron-free gear additive and method for producing same
US5922656A (en) * 1997-03-24 1999-07-13 Tonen Corporation Lubricant compositions for automatic transmissions
US6559105B2 (en) * 2000-04-03 2003-05-06 The Lubrizol Corporation Lubricant compositions containing ester-substituted hindered phenol antioxidants
US6569818B2 (en) * 2000-06-02 2003-05-27 Chevron Oronite Company, Llc Lubricating oil composition
US6593281B2 (en) * 2000-06-05 2003-07-15 Tonengeneral Sekiyu K.K. Lubricating oil composition for automatic transmission
US6720293B2 (en) * 2000-09-25 2004-04-13 Infineum International Ltd. Low viscosity lubricating oil compositions
US6764982B2 (en) * 2001-02-07 2004-07-20 The Lubrizol Corporation Lubricating oil composition
US20030004070A1 (en) * 2001-06-15 2003-01-02 Keith Strickland Gas-fuelled engine lubricating oil compositions
US6673751B1 (en) * 2002-11-06 2004-01-06 The Lubrizol Corporation Boron containing overbased calixarates and lubricants and methods thereof
US20040102335A1 (en) * 2002-11-25 2004-05-27 The Lubrizol Corporation Additive formulation for lubricating oils

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040214729A1 (en) * 2003-04-25 2004-10-28 Buitrago Juan A. Gear oil composition having improved copper corrosion properties
US20080300155A1 (en) * 2003-04-25 2008-12-04 Chevron Oronite Company, Llc Gear oil having low copper corrosion properties
US7871965B2 (en) 2003-04-25 2011-01-18 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US20110092401A1 (en) * 2003-04-25 2011-04-21 Buitrago Juan A Gear oil having low copper corrosion properties
US8389449B2 (en) 2003-04-25 2013-03-05 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US8536102B2 (en) 2003-04-25 2013-09-17 Chevron Oronite Company Llc Gear oil having low copper corrosion properties
US20230167380A1 (en) * 2020-05-05 2023-06-01 Totalenergies Onetech Lubricating composition for electric vehicles

Also Published As

Publication number Publication date
EP1518919A1 (en) 2005-03-30
CA2480114A1 (en) 2005-03-25
SG110161A1 (en) 2005-04-28
AU2004210592A1 (en) 2005-04-14
JP2005097615A (ja) 2005-04-14
US20070054813A1 (en) 2007-03-08
JP2012046769A (ja) 2012-03-08
MXPA04009160A (es) 2005-03-31

Similar Documents

Publication Publication Date Title
US20070054813A1 (en) Boron free automotive gear oil
EP0856042B1 (en) Automatic transmission with an automatic transmission fluid of improved friction durability
EP0978555B1 (en) Lubricating oil formulations
EP2028256B1 (en) Lubricating oils having improved friction stability
US5885943A (en) Sulfur boron antiwear agents for lubricating compositions
US6303547B1 (en) Friction modified lubricants
EP0799291B1 (en) Engine oil with improved fuel economy properties
AU657563B2 (en) Oil additive concentrates and lubricants of enhanced performance capabilities
JP4007884B2 (ja) 摩擦改良潤滑剤
CA2159120A1 (en) Gear oil compositions
KR20040084862A (ko) 2 식 기어 윤활 제형
EP2028257B1 (en) Use of boron-containing additive composition in lubricating oils to improve friction stability
JP4159774B2 (ja) 自動車緩衝器用潤滑油組成物
US20040224858A1 (en) Low sulfur, low ash, and low phosphorus lubricant additive package using overbased calcium phenate
US20040220059A1 (en) Low sulfur, low ash, low and phosphorus lubricant additive package using overbased calcium oleate
JP2003055681A (ja) 潤滑油組成物
WO1997004051A1 (en) Power transmitting fluids with improved resistance to foaming
AU2008202852A1 (en) Lubricating oils having improved friction stability

Legal Events

Date Code Title Description
AS Assignment

Owner name: ETHYL PETROLEUM ADDITIVES, INC., VIRGINIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:HEWETTE, CHIP;MILNER, JEFFREY L.;REEL/FRAME:014550/0439

Effective date: 20030925

AS Assignment

Owner name: SUNTRUST BANK, AS ADMINISTRATIVE AGENT, GEORGIA

Free format text: SECURITY AGREEMENT;ASSIGNOR:ETHYL PETROLEUM ADDITIVES, INC.;REEL/FRAME:014782/0317

Effective date: 20040618

AS Assignment

Owner name: AFTON CHEMICAL CORPORATION, VIRGINIA

Free format text: CHANGE OF NAME;ASSIGNOR:ETHYL PETROLEUM ADDITIVES, INC.;REEL/FRAME:015918/0557

Effective date: 20040701

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

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION

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