WO1987005927A2 - Lubricant composition - Google Patents

Lubricant composition Download PDF

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Publication number
WO1987005927A2
WO1987005927A2 PCT/US1987/000715 US8700715W WO8705927A2 WO 1987005927 A2 WO1987005927 A2 WO 1987005927A2 US 8700715 W US8700715 W US 8700715W WO 8705927 A2 WO8705927 A2 WO 8705927A2
Authority
WO
WIPO (PCT)
Prior art keywords
lubricant mixture
lubricant
fatty
mixture
carbon atoms
Prior art date
Application number
PCT/US1987/000715
Other languages
English (en)
French (fr)
Other versions
WO1987005927A3 (en
Inventor
James Jay Schwind
Craig Daniel Tipton
Original Assignee
The Lubrizol Corporation
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 IN237/DEL/87A priority Critical patent/IN169147B/en
Application filed by The Lubrizol Corporation filed Critical The Lubrizol Corporation
Publication of WO1987005927A2 publication Critical patent/WO1987005927A2/en
Publication of WO1987005927A3 publication Critical patent/WO1987005927A3/en

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    • 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
    • C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/02—Well-defined hydrocarbons
    • C10M105/06—Well-defined hydrocarbons aromatic
    • 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
    • C10M105/32—Esters
    • C10M105/36—Esters of polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
    • C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen 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
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/74—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing phosphorus
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/76—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing silicon
    • C—CHEMISTRY; METALLURGY
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
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    • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
    • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
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    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/04—Hydroxy compounds
    • C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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    • C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
    • C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/16—Amides; Imides
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02—Sulfurised compounds
    • C10M135/04—Hydrocarbons
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    • C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C—CHEMISTRY; METALLURGY
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    • C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
    • C10M135/10—Sulfonic acids or derivatives thereof
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    • C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
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    • C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
    • C10M137/04—Phosphate esters
    • C10M137/10—Thio derivatives
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    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
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    • 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
    • C10M141/12—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 compound containing atoms of elements not provided for in groups C10M141/02 - C10M141/10
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    • C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
    • C10M143/06—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation containing butene
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    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
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    • C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
    • C10M155/02—Monomer containing silicon
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    • C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
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    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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    • 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
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    • C10M2203/06—Well-defined aromatic compounds
    • C10M2203/065—Well-defined aromatic compounds used as base material
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    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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Definitions

  • This invention relates to a lubricating composition, and, in particular, to manual transmission fluids.
  • Transmission fluids particularly those for synchromesh manual transmissions, have typically been based upon high weight mineral oils, e.g., 80 weight oil, engine oils, differential oils and automatic transmission fluids.
  • the lighter of these oils, e.g., automatic transmission fluid thins out too much at the high temperatures reached during summertime driving resulting in objectional gear noise. While the heavier of these oils are acceptable under normal summertime driving conditions, difficulties are often encountered in cold weather conditions. The viscosity of the heavier mineral oils increases substantially in the winter due to low temperatures.
  • the shifting characteristics for the manual transmission are then significantly hindered due to the thickened oil. The hindered operation of the manual transmission requires greater effort to shift the gears. In extreme cases, this has resulted in a broken shifting lever.
  • a second problem which faces a synchromesh transmission is that of double detent or double bump. This phenomena results when the static coefficient of friction is too high and the cone and ring cannot engage due to insufficient slippage to allow smooth engaging. A further problem arises if the dynamic coefficient of friction is too low as clashing is observed. The clashing arises because the relative velocity of the blocker ring and cone assembly does not go to zero before engagement.
  • the present invention provides a solution to double detent through the formulation of a manual transmission fluid which exhibits high dynamic friction properties as well as low static friction properties.
  • Various components of the present invention are known in lubricating fluids.
  • United States Patent 4,031,023 issued June 21, 1977 to Musser and Koch discloses the use of viscosity improvers to impart a liquid character to a lubricating composition.
  • Musser et al also discloses synthetic lubricating oils, extreme pressure (EP) agents and dispersants.
  • the term dispersants as utilized by Musser et al include materials which suspend or disperse sludge and which are described as being oil-soluble, and stably dispersible in lubricating compositions.
  • the present invention describes a synthetic lubricant mixture suitable for a manual transmission fluid comprising: (a) an alkaline earth metal salt selected from the group consisting of sulfonates, phenates, oxylates, carboxylates and mixtures thereof;
  • a friction modifier selected from the group consisting of fatty phosphites, borated fatty epoxides, borated glycerol monocarboxylates, borated alkoxylated fatty amines and mixtures thereof;
  • the first aspect of the present invention is the alkaline earth metal salt which has been found particularly useful to assist in the frictional properties in the manual transmission fluid compositions.
  • the salt may be a phenate, oxylate, carboxylate or preferably a sulfonate. It has been determined that the preferred salt is a magnesium sulfonate. Calcium salts are adequate for usage alone in the present invention but when used are preferably in combination with the magnesium sulfonate salts. Barium salts may also be used herein.
  • the sulfonate salts are those having a substantially oleophilic character and which are formed from organic materials.
  • Organic sulfonates are well known materials in the lubricant and detergent arts.
  • the sulfonate compound should contain on average from about 10 to about 40 carbon atoms, preferably from about 12 to about 36 carbon atoms and preferably from about 14 to about 32 carbon atoms on average. Similarily, the phenates, oxylates and carboxylates have a substantially oleophilic character.
  • the present invention allows for the carbon atoms to be either aromatic or in a paraffinic configuration, it is highly preferred that alkylated aromatics be employed. While naphthalene based materials may be employed, the aromatic of choice is the benzene moiety.
  • composition is thus a mono-sulfonated alkylated benzene, and is preferably the mono-alkylated benzene.
  • alkyl benzene fractions are obtained from still bottom sources and are mono- or di-alkylated.
  • the mono-alkylated aromatics are superior to the di-alkylated aromatics in overall properties.
  • the use of mono-functional (e.g., mono-sulfonated) materials avoids crosslinking of the molecules with less precipitation of the salt in the transmission.
  • a mixture of mono-alkylated aromatics (benzene) be utilized to obtain the mono-alkylated salt (benzene sulfonate) in the present invention.
  • the amount of the salt utilized in the present invention is typically from about 0.5% to about 8%, preferably from about 0.75% to about 6%, and most preferably from about 1% to about 5% by weight of the total composition. For maximum effectiveness, the salt should Be greater than 3% by weight of the composition.
  • the salt be "overbased".
  • overbasing it is meant that a stoichiometric excess of the alkaline earth metal be present over that required to neutralize the anion of the salt.
  • the excess metal from overbasing has the effect of neutralizing acids which may build up in the lubricant.
  • the overbased salt increases the dynamic coefficient of friction.
  • the excess alkaline earth metal will be present over that which is required to neutralize the anion at about 10:1 to 30:1, preferably 11:1 to 18:1 on an equivalent basis.
  • the second required component of the manual transmission fluid of the present invention is a friction modifier such as a fatty phosphite.
  • the phosphites are generally of the formula (RO) 2 PHO.
  • the preferred dialkylated phosphite as shown in the preceding formula is typically present with a mono-alkylated phosphite of theformula (RO) (HO) PHO. Both of these phosphites are concomitantly produced and thus mixture of the mono-phosphite and the di-phosphite is present.
  • the mixtures of the phosphites are typically such that the weight ratio of the mono-phosphite to the di-phosphite is from about 2:1 to about 1 : 4 by weight. It is, of course, highly desirable that the di-phosphite be present in an excess over the mono-phosphite.
  • the term "R” has been referred to as an alkyl group. It is, of course, possible that the alkyl is alkenyl and thus the terms “alkyl” and “alkylated”, as used herein, embrace other than saturated alkyl groups within the phosphite.
  • the phosphite utilized herein is thus one having sufficient hydrocarbyl groups to render the phosphite substantially oleophilic and further that the hydrocarbyl groups are preferably substantially unbranched.
  • the phosphite contain from about 10 to about 24 carbon atoms in each of the fatty radicals described as "R".
  • the inclusion of substantial amounts of the mono-alkylated phosphite require that the radical "R" contain a- larger number of carbon atoms.
  • the fatty phosphite contains from about 12 to about 22 carbon atoms in each of the fatty radicals, most preferably from about 16 to about 20 carbon atoms in each of the fatty radicals. It is highly preferred that the fatty phosphite be formed from oleyl groups, thus having 18 carbon atoms in each fatty radical.
  • Borated fatty epoxides are known from Canadian Patent 1,188,704 issued June 11, 1985 to Davis.
  • the oil-soluble boron-containing compositions of Davis are prepared by reacting at a temperature from about 80°C to about 250°C,
  • R 1 R 2 C[O]CR 3 R 4 wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or an aliphatic radical, or any two thereof together with the epoxy carbon atom or atoms to which they are attached, form a cyclic radical, said epoxide containing at least 8 carbon atoms.
  • the borated fatty epoxides are characterized by the method for their preparation which involves the reaction of two materials.
  • Reagent A may be boron trioxide or any of the various forms of boric acid, including metaboric acid (HBO 2 ), orthoboric acid (H 3 BO 3 ) and tetraboric acid (H 2 B 4 O 7 ) .
  • Boric acid, and especially orthoboric acid, is preferred.
  • Reagent B is at least one epoxide having the above formula and containing at least 8 carbon atoms.
  • each of the R values is most often hydrogen or an aliphatic radical with at least one being an aliphatic radical containing at least 6 carbon atoms.
  • aliphatic radical includes aliphatic hydrocarbon radicals (e.g., hexyl, heptyl, octyl, decyl, dcdecyl, tetradecyl, stearyl, hexenyl, oleyl), preferably free from, acetylenic unsaturation; substituted aliphatic hydrocarbon radicals including substituents such as hydroxy, nitro, carbalkoxy, alkoxy and alkylthio (especially those containing a lower alkyl radical; i.e., one containing 7 carbon atoms or less); and hetero atom-containing radicals in which the hetero atoms may be, for example, oxygen, nitrogen or sulfur.
  • the aliphatic radicals are preferably alkyl radicals, and more preferably those containing from about 10 to about 20 carbon atoms. Mixtures of epoxides may be used; for example, commercial available C 14- 16 or
  • R 1 is a mixture of alkyl radicals having two less carbon atoms than the epoxide.
  • R 1 is a straight-chain alkyl radical and especially the tetradecyl radical.
  • Further useful epoxides are those in which any two of the R radicals form a cyclic radical, which may be alicyclic or heterocyclic. Examples are n-butylcyclo pentene oxide, n-hexylcyclohexene oxide, methylenecyclooctene oxide and 2-methylene-3-n-hexyltetrahydrofuran oxide.
  • the borated fatty epoxides may be prepared by merely blending the two reagents and heating them at a temperature from about 80° to about 250°C., preferably from about 100° to about 200°C., for a period of time sufficient for reaction to take place.
  • the reaction may be effected in the presence of a substantially inert, normally liquid organic diluent such as toluene, xylene, chlorobenzene, dimethylformamide or the like, but the use of such diluents is usually unnecessary.
  • water is evolved and may be removed by distillation.
  • the molar ratio of reagent A to reagent B is generally between about 1:0.25 and about 1:4. Ratios between about 1:1 and about 1:3 are preferred, with 1:2 being an especially preferred ratio.
  • alkaline reagents include inorganic bases and basic salts such as sodium hydroxide, potassium hydroxide and sodium carbonate; metal alkoxides such as sodium methoxide, potassium t-butoxide and calcium eth ⁇ xide; heterocyclic amines such as piperidine, morpholine and pyridine; and aliphatic amines such as n-butylamine, di-n-hexylamine and tri-n-butylamine.
  • the preferred alkaline reagents are the aliphatic and heterocyclic amines and especially tertiary amines. When the preferred method involving the "heel" is used, the alkaline reagent is typically added to the blend of the "heel" with reagent A.
  • compositions of this invention are not known with certainty.
  • water is evolved in near-stoichiometric amounts for conversion of boric acid to boron trioxide when reagent A is boric acid, and gel permeation chromatography of the composition prepared from boric acid and a C 16 alpha-olefin oxide mixture in a 1:2 molar ratio indicates the presence in substantial amounts of three constituents having approximate molecular weights of 400, 600 and 1200.
  • the borated amines are generally known from European published applications 84 302 342.5 filed April 5, 1984 and 84 307 355.2 filed October 25, 1984, both authored by Reed Walsh.
  • the borated amine friction modifiers are conveniently prepared by the reaction of a boron compound selected from the group consisting of boric acid, boron trioxide and boric acid esters of the formula B (OR) 3 wherein R is a hydrocarbon-based radical containing from 1 to about 8 carbon atoms and preferably from about 1 to about 4 carbon atoms with an amine selected from the group consisting of hydroxy containing tertiary amines corresponding to the formulae
  • R 1 in each formula is a lower alkylene based radical containing from 1 to about
  • R 2 is a radical selected from the group consisting of hydrocarbon based radicals containing from 1 to about 100 carbon atoms and alkoxy radicals of the structure H(OR 4 ) y - where R 4 is a lower alkylene based radical containing from 1 to about 8 carbon atoms, R 3 and R 5 (pendent from the ethylenic carbon in the 2 position in the imidazolene (Z) radical) are each hydrocarbon based radicals containing from 1 to about 100 carbon atoms, x and y are each an integer ranging from at least 1 to about 50 and the sum of x+y is at most 75.
  • the amines useful in preparing the organo-borate additive compositions are those tertiary amines corresponding to (A) above wherein R 2 is an alkoxy radical of the structure H(OR 4 ) y - wherein R 4 is a lower alkylene radical containing from 1 to about 8 carbon atoms and R 3 is an aliphatic based hydrocarbon radical containing from about 8 to about 25 carbon atoms, and preferably from about 10 to about 20 carbon atoms and x and y are each an integer ranging from at least 1 to about
  • Preferred tertiary amines useful in preparing the multifunctional organo-borate additive compositions are those tertiary amines corresponding to formula (A) above wherein
  • R 2 is an alkoxy radical of the structure H(OR 4 ) y -, wherein
  • R 1 and R 4 are individually ethylene or propylene radicals
  • R 3 is an alkyl or an alkenyl based hydrocarbon radical containing from about 10 to about 20 carbon atoms
  • x and y are each an integer ranging from at least 1 to about 9 and preferably from at least 1 to about 5 and the sum of x+y is at most 10 and preferably at most 5, i.e., the sum of x+y ranges from about 2 to about 10 and preferably from about 2 to about 5 respectively.
  • hydrocarbon-based radical denotes a radical having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character within the context of this invention.
  • radicals include the following:
  • Hydrocarbon radicals that is, aliphatic, (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl), aromatic, aliphatic- and alicyclic-substituted aromatic, aromatic-substituted aliphatic and alicyclic radicals, and the like, as well as cyclic radicals wherein the ring is completed through another portion of the molecule (that is, any two indicated hydrocarbon radicals, e.g., R 2 and R 3 , may together form an alicyclic radical and such radical may contain heteroatoms such as nitrogen, oxygen and sulfur).
  • aliphatic e.g., alkyl or alkenyl
  • alicyclic e.g., cycloalkyl or cycloalkenyl
  • radicals are known to those skilled in the art; representative examples are examples of such radicals as represented by R 2 , R 3 and R 5 in the formulae above include methyl, ethyl, butyl, hexyl, octyl, decyl, dodecyl, tetradecyl, octadecyl, eicosyl, cyclohexyl, phenyl and naphthyl and the like including all isomeric forms of such radicals and when R 2 and R 3 together form an alicyclic radical, then examples of such radicals include morpholinyl, piperidyl, piperazinyl, phenothiazinyl, pyrrolyl, pyrrolidyl, thiazolidinyl and the like.
  • Substituted hydrocarbon radicals that is, radicals containing non-hydrocarbon substituents which, in the context of this invention, do not alter the predominantly hydrocarbon character of the radical.
  • substituents representative examples are hydroxy (HO-); alkoxy (RO-); carbalkoxy (RO 2 C-); acyl [RC(O)-]; acyloxy (RCO 2 -); carboxamide (H 2 NC(O)-); acylimidazyl; [RC(NR)-]; nitro-(-NO 2 ); and alkylthio (RS-) and halogen atoms (e.g., F, Cl, Br and I).
  • Hetero radicals that is, radicals which, while predominantly hydrocarbon, contain atoms other than carbon present in a chain or ring otherwise composed of carbon atoms.
  • Suitable hetero atoms will be apparent to those skilled in the art and include, for example, nitrogen, oxygen and sulfur. In general, no more than about three substituents or hetero atoms, and preferably no more than one, will be present for each 10 carbon atoms in the hydrocarbon-based radical.
  • alkyl-based radical alkenyl-based radical and alkylene-based radical
  • tertiary amine compounds useful in preparing the organo-borate compounds of this invention include monoalkoxylated amines such as dimethylethanolamine, diethylethanolamine, dibutylethanolamine, diisopropylethanolamine, di(2-ethylhexyl) ethanolamine, phenylethylethanolamine, dibutylisopropanolamine, dimethylisopropanolamine and the like and polyalkoxylated amines such as methyldiethanolamine, ethyldiethanolamine, phenyldiethanolamine, diethyleneglycol mono-N-morpholinoethyl ether, N-(2-hydroxyethyl)thiazolidine, 3-morpholinopropyl-(2-hydroxyethyl)
  • ETHOMEEN an especially preferred class of tertiary amines useful in preparing the organo-borate compounds of the invention is that constituting the commercial alkoxylated fatty amines known by the trademark "ETHOMEEN” and available from the Armak Company.
  • Representative examples of these ETHOMEEN is ETHOMEEN C/12 (bis [2-hydroxyethyl] cocoamine); ETHOMEEN C/20 (polyoxyethylene [10] cocoamine); ETHOMEEN S/12 (bis [2-hydroxyethyl]soyamine); ETHOMEEN T/12 (bis [2-hydroxyethyl]tallowamine); ETHOMEEN T/15- (polyoxyethylene-[5]tallowamine); ETHOMEEN 0/12(bis[2-hydroxyethyl]oleyl-amine; ETHOMEEN 18/12 (bis [2-hydroxyethyl]octadecylamine; ETHOMEEN 18/25 (polyoxyethylene- [15]octadecylamine and the like.
  • the tertiary amine reactants represented by formulae (A) and (B) above may be reacted first with elemental sulfur to sulfurize any carbon-to-carbon double bond unsaturation which may be present in the hydrocarbon based radicals R 2 , R 3 and R 5 when these radicals are, for example, alkenyl radicals (e.g., fatty oil or fatty acid radicals).
  • the sulfurization reaction will be carried out at temperatures ranging from about 100°C. to about 250°C. and preferably from about 150°C. to about 200°C.
  • the molar ratio of sulfur to amine can range from about 0.5:1.0 to about 3.0:1.0 and preferably 1.0:1.0.
  • catalysts may be employed, if desired. If such catalysts are employed, preferably such catalysts are tertiary hydrocarbon substituted amines, most preferably, trialkylamines. Representative examples of which include tributylamine, dimethyloctylamine, triethylamine and the like.
  • the organo-borate additive friction modifiers can be prepared by adding the boron reactant, preferably boric acid, to at least one of the above defined tertiary amine reactants, in a suitable reaction vessel, and heating the resulting reaction mixture at a temperature ranging from about 50° to about 300°C with continuous stirring. The reaction is continued until by-product water ceases to evolve from the reaction mixture indicating completion of the reaction. The removal of by-product water is facilitated by either blowing an inert gas, such as nitrogen, over the surface of the reaction mixture or by conducting the reaction at reduced pressures.
  • the reaction between the boron reactant and the tertiary amine will be carried out at temperatures ranging from about 100°C to about 250°C and most preferably between about 150°C and 230°C while blowing with nitrogen.
  • the amines will be liquid at room temperature, in those instances where the amine reactant is a solid or semi-solid, it will be necessary to heat the amine to above its melting point in order to liquify it prior to the addition of the boron-containing reactant thereto.
  • the melting point of the amine can readily determine the melting point of the amine either from the general literature or through a simple melting point analysis.
  • the amine reactant alone will serve as the solvent for the reaction mixture of the boron containing reactant and amine reactant.
  • an inert normally liquid organic solvent can be used such as mineral oil, naptha, benzene, toluene or xylene can be used as the reaction media.
  • the organo-borate additive compound is to be added directly to a lubricating oil, it is generally preferred to conduct the reaction merely using the amine reactant as the sole solvent.
  • the borated fatty acid esters of glycerol are prepared by borating a fatty acid ester of glycerol with boric acid with removal of the water of reaction.
  • a fatty acid ester of glycerol with boric acid with removal of the water of reaction.
  • there is sufficient boron present such that each boron will react with from 1.5 to 2.5 hydroxyl groups present in the reaction mixture.
  • the reaction may be carried out at a temperature in the range of 60°C to 135°C, in the absence or presence of any suitable organic solvent such as methanol, benzene, xylenes, toluene, neutral oil and the like.
  • any suitable organic solvent such as methanol, benzene, xylenes, toluene, neutral oil and the like.
  • Fatty acid esters of glycerol can be prepared by a variety of methods well known in the art. Many of these esters, such as glycerol monooleate and glycerol tallowate, are manufactured on a commercial scale.
  • the esters useful are oil-soluble and are preferably prepared from C 8 to C 22 fatty acid or mixtures thereof such as are found in natural products.
  • the fatty acid may be saturated or unsaturated.
  • Certain compounds found in acids from natural sources may include licanic acid which contains one keto group.
  • Most preferred C 8 to C 22 fatty acids are those of the formula RCOOH wherein R is alkyl or alkenyl.
  • the fatty acid monoester of glycerol is preferred, however, mixtures of mono- and diesters may be used.
  • any mixture of mono- and diester contains at least 40% of the monoester.
  • mixtures of mono- and diesters of glycerol contain from 40 to 60 percent by weight of the monoester.
  • commercial glycerol monooleate contains a mixture of from 45% to 55% by weight monoester and from 55% to 45% diester.
  • Preferred fatty acids are oleic, stearic, isostearic, palmitic, myristic, palmitoleic, linoleic, lauric, linolenic, and eleostearic, and the acids from the natural products tallow, palm oil, olive oil, peanut oil, corn oil, neat's foot oil and the like.
  • a particularly preferred acid is oleic acid.
  • the borated fatty acid esters are conveniently stabilized against hydrolysis by reacting the esters with an alkyl or alkenyl mono- or bis-succinimide.
  • the amount of the friction modifier employed in the transmission fluids of the present invention is typically from about 0.1% to about 5%, preferably from about 0.25% to about 4%, and most preferably from about 0.5% to about 3.5% by weight of the total composition.
  • a sulfurized olefin is included in the present invention as an extreme pressure agent. Extreme pressure agents are materials which retain their character and prevent metal to metal damage, e.g., contact, when gears are engaged and meshed. The sulfurization of olefins is generally known as is evidenced by United States Patent 4,191,659 as previously disclosed.
  • the sulfurized olefins which are useful in the present invention are those materials formed from olefins which been reacted with sulfur.
  • an olefin is defined as a compound having a double bond connecting two aliphatic carbon atoms.
  • R values in the above formula which are not hydrogen may be satisfied by such groups as -C(R 5 ) 3 , -COOR 5 , -CON(R 5 ) 2 , -COON(R 5 ) 4 , -COOM, -CN,
  • Each R 5 is independently hydrogen, alkyl, alkenyl, aryl, substituted alkyl, substituted alkenyl or substituted aryl, with the proviso that any two R 5 groups can be alkylene or substituted alkylene whereby a ring of up to about 12 carbon atoms is formed;
  • M is one equivalent of a metal cation (preferably Group I or II, e.g., sodium, potassium, magnesium, barium, calcium);
  • X is halogen (e.g., chloro, bromo, or iodo);
  • Y is oxygen or divalent sulfur
  • Ar is an aryl or substituted aryl radical of up to about 12 carbon atoms. Any two of R 1 , R 2 , R 3 and R 4 may also together form an alkylene or substituted alkylene group; i.e., the olefinic compound may be alicyclic.
  • substituents in the substituted moieties described above are not normally a critical aspect of the invention and any such substituent is useful so long as it is, or can be made compatible, with lubricating environments and does not interfere under the contemplated reaction conditions.
  • substituted compounds which are so unstable as to deleteriously decompose under the reaction, conditions employed are not contemplated.
  • certain substituents such as keto or aldehydo can desirably undergo sulfurization.
  • the selection of suitable substituents is within the skill of the art or may be established through routine testing.
  • substituents include any of the above-listed moieties as well as hydroxy, amidine, amino, sulfonyl, sulfinyl, sulfonate, nitro, phosphate, phosphite, alkali metal mercapto and the like.
  • the olefinic compound is usually one in which each R value which is not hydrogen is independently alkyl, alkenyl or aryl, or (less often) a corresponding substituted radical.
  • Monoolefinic and diolefini ⁇ compounds, particularly the former, are preferred, and especially terminal monoolefinic hydrocarbons; that is, those compounds in which R 3 and R 4 are hydrogen and R 1 and R 2 are alkyl or aryl, especially alkyl (that is, the olefin is aliphatic).
  • Olefinic compounds having about 3 to 30 and especially about 3 to 18 (most often less than 9) carbon atoms are particularly desirable.
  • Isobutene, propylene and their oligomers such as dimers, trimers and tetramers, and mixtures thereof are especially preferred olefinic compounds.
  • isobutylene and diisobutylene are particularly desirable because of their availability and the particularly desirable because of their availability and the particularly high sulfur-containing compositions which can be prepared therefrom.
  • the sulfurized olefins useful in the present invention as extreme pressure agents are typically utilized at from about 0.1% to about 5%, preferably from about 0.25% to about 4% and, most preferably from about 0.5% to about 3.5% by weight of the total composition.
  • Various sulfurized olefins which are useful in the present invention are shown in Table I below:
  • the synthetic lubricating oils useful herein include hydrocarbon oils and halosubstituted hydrocarbon oils such as polymerized and interpolymerized olefins (e.g., polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, etc.); poly(1-hexenes), poly(1-octenes), poly(1-decenes), etc.
  • alkylbenzenes e.g., dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes, etc.
  • polyphenyls e.g., biphenyls, terphenyls, 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 lubricating oils that can be used. These 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., methylpolyisopropylene 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 -C 8 fatty acid esters, or the C 1 3 Oxo acid diester of tetra-ethylene glycol.
  • Another suitable class of synthetic lubricating oils that can be used comprises 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.).
  • dicarboxylic acids e.g., phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid,
  • esters include dibutyl adipate, di(2-e2hylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl 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 C 5 to C 12 monocarboxylic acids and polyols and polyol ethers such as neopentyl glycol, trimethylol propane, pentaerythritol, dipentaerythritol, tripentaerythritol, etc.
  • Silicon-based oils such as the polyalkyl-, polyaryl-, polyalkoxy- or polyaryloxy-siloxane oils and silicate oils comprise another useful class of synthetic lubricants (e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(4-methyl-hexyl)-silicate, tetra-(p-tert-butylphenyl)silicate, hexyl- (4-methyl-2-pentoxy)disiloxane, poly(me hyl)siloxanes, poly(methylphenyl)siloxanes, etc.).
  • synthetic lubricants e.g., tetraethyl silicate, tetraisopropyl silicate, tetra-(2-ethylhexyl)silicate, tetra-(
  • Other synthetic lubricating oils include liquid esters of phosphorus ⁇ containing acids (e.g., tricresyl phosphate, trioctyl phosphate, diethyl ester of decane phosphonic acid, etc.), polymeric tetrahydrofurans and the like.
  • Polyolefin oligomers are typically formed by the polymerization reaction of alpha-olefins.
  • Nonalphaolefins may be oligomerized to give a synthetic oil within the present invention, however, the reactivity and availability of alpha-olefins at low cost dictates their selection as the source of the oligomer.
  • the polyolefin oligomer synthetic lubricating oils of interest in the present invention include hydrocarbon oils and halo-substituted hydrocarbon oils such as are obtained as the polymerized and interpolymerized olefins, e.g., oligomers, include the polybutylenes, polypropylenes, propylene-isobutylene copolymers, chlorinated polybutylenes, poly (1-hexenes), poly(1-octenes), poly(1-decenes), similar materials and mixtures thereof.
  • the oligomer is obtained from a monomer containing from about 6 to 18 carbon atoms, preferably from about 8 carbon atoms to about 12 carbon atoms.
  • the monomer used to form the oligomer is decene, and preferably 1-decene.
  • the nomenclature alpha-olefin is a trivial name and the IUPAC nomenclature of a 1-ene compound may be considered to have the same meaning within the present invention.
  • the oligomer While it is not essential that the oligomer be formed from an alpha-olefin, such is desirable.
  • the reason for forming the oligomer from an alpha-olefin is that branching will naturally occur at the points where the olefin monomers are joined together and any additional branching within the backbone of the olefin can provide too high a viscosity of the end oil.
  • the polymer formed from the alpha olefin be hydrogenated. The hydrogenation is conducted according to known practices. By hydrogenating the polymer free radical attack on the allyic carbons remaining after polymerization is minimized.
  • the molecular weight of the oligomer is typically averages from about 250 to about 1400, conveniently from about 280 to about 1200 preferably from about 300 to about 1100 and most preferably about 340 to about 520.
  • the choice of molecular weight of the oligomer is largely dependent upon whether a viscosity improver is included within the formulation. That is, the polyolefin oligomer, may require either a thickening or a thinning effect to ensure that the proper lubricating viscosities are maintained under extreme heat and cold conditions.
  • a further desirable synthetic lubricant is an alkylated aromatic compound.
  • the alkylated aromatic compounds are particularly beneficial in improving the low temperature flow characteristics.
  • the alkylated aromatics may be referred to, supra, under the discussion of the alkaline earth metal salt.
  • the alkylated aromatics are the same base materials utilized to manufacture the aromatic sulfonate.
  • the alkylated aromatic compound may be obtained in mixture with the sulfonate due to incomplete sulfonation of the alkylated aromatic.
  • the alkylated aromatic may be obtained directly.
  • the aromatic nucleus of the alkylated aromatic compound is benzene.
  • a particularly useful synthetic lubricant is a mixture of the alpha olefin oligomer and the alkylated aromatic. Typically, a mixture of the oligomer to the alkylated aromatic will be at a weight ratio of about 8:1 to about 1:8.
  • the amount of the synthetic lubricant which is employed in the present invention is typically from about 4% to about 98%, with intermediate ranges of about 7% to about 96%, and about 5% to about 95% by weight of the composition.
  • the variability in the amount of the synthetic lubricant utilized in the present invention is largely because the synthetic lubricant may be obtained as a separate material with components A through C inclusive being utilized as a concentrate. That is, components A through C require more specialized processing conditions than the formation of the synthetic lubricant and thus it is often convenient to ship components A through C for blending with the synthetic lubricant.
  • components (A), (B) and (C) are conveniently obtained at from 95% to 50% by weight of the composition and the synthetic lubricant is obtained at 5% to 50% by weight of the composition.
  • Viscosity improving materials as previously referred to may be included in the compositions of the present invention.
  • the viscosity index improvers typically include polymerized and copolymerized alkyl methacrylates and mixed esters of styrene-maleic anhydride interpolymers reacted with nitrogen-containing compounds.
  • Polyisobutylene compounds are also typically used as viscosity index improvers.
  • the amount of viscosity improver which may be typically added to the fully formulated manual transmission fluid composition is about 1% to about 50%, preferably about 10% to about 25% by weight.
  • Zinc salts are also added to manual transmission lubricants.
  • Zinc salts are ordinarily utilized as extreme pressure agents such as zinc dithiophosphates.
  • the zinc salts are added at levels measured by weight of the zinc metal at from about 0.02% to about 0.2%, preferably from about 0.04% to about 0.15% by weight.
  • Mineral oil such as 100 neutral oil may be included in the present invention. That is, it may be desirable as the mineral oil is less expensive than the oligomer to formulate the composition removing a portion of the oligomer and replacing the same with the mineral oil. Thus, when mineral oil is utilized in the composition of the present invention, it may be present at from 0.1% to about 75%, preferably from about 0.5% to about 50% by weight of the total composition.
  • Additional ingredients which may be included in the manual transmission fluid of the present invention are fatty acid amides which are useful as additional friction modifiers, particularly for reducing the static coefficient of friction.
  • Further useful components herein include seal swell agents such as sulfones and sulfolanes. Suitable seal swell agents are disclosed in United States Patent 4,029,587 to Koch issued June 14, 1977.
  • a still further useful component in the present invention is a foam suppression agent such as a silicone oil. Any other typical ingredient may be included herein such as pour point depressants, dyes, odorants and the like.
  • the products of the present invention are obtained as a light orange, nearly clear liquid. Typical prior art manual transmission fluids will turn black after extended useage and a visible inspection is thus not possible.
  • compositions of the present invention are that the products may be visually examined for contaminants. Such contaminants may indicate the failure of seals or metal parrs within the manual transmission.
  • a particular utility of the products of the present invention in addition to being highly effective in having a high dynamic and a low static coefficient of friction is that they may be visually examined for deterioration of the transmission or contamination of the transmission fluid.
  • the products herein are also of relatively low viscosity at temperatures of -25°C and thus shift easily.
  • a manual transmission fluid is prepared by combining the following ingredients:
  • foam inhibitor which is a polydimethyl siloxane.
  • a manual transmission fluid is prepared by combining the following ingredients:
  • foam inhibitor which is a polydimethyl siloxane.
  • magnesium alkyl benzene sulfonate (overbased) wherein the alkyl contains about 24 carbon atoms on average.
  • the product herein has a high dynamic coefficient of friction and a low static coefficient of friction. Cold weather viscosity is such that shifting is easily accomplished.
  • the product is a light orange in color.
  • a manual transmission fluid is prepared by combining the following ingredients:
  • foam inhibitor which is a polydimethyl siloxane.
  • the product herein has a high dynamic coefficient of friction and a low static coefficient of friction. Cold weather viscosity is such that shifting is easily accomplished.
  • the product is a light orange in color.
  • a manual transmission fluid is prepared by combining the following ingredients:
  • foam inhibitor which is a polydimethyl siloxane.
  • the product herein has a high dynamic coefficient of friction and a low static coefficient of friction. Cold weather viscosity is such that shifting is easily accomplished.
  • the product is a light orange in color.
  • EXAMPLE V A manual transmission fluid is prepared by combining the following ingredients:
  • foam inhibitor which is a polydimethyl siloxane.
  • the product herein has a high dynamic coefficient of friction and a low static coefficient of friction. Cold weather viscosity is such that shifting is easily accomplished.
  • the product is a light orange in color.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Lubricants (AREA)
PCT/US1987/000715 1986-04-04 1987-04-02 Lubricant composition WO1987005927A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IN237/DEL/87A IN169147B (enrdf_load_stackoverflow) 1986-04-04 1987-03-19

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US84843386A 1986-04-04 1986-04-04
US848,433 1986-04-04

Publications (2)

Publication Number Publication Date
WO1987005927A2 true WO1987005927A2 (en) 1987-10-08
WO1987005927A3 WO1987005927A3 (en) 1988-03-24

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PCT/US1987/000715 WO1987005927A2 (en) 1986-04-04 1987-04-02 Lubricant composition

Country Status (8)

Country Link
CN (1) CN1018843B (enrdf_load_stackoverflow)
AU (1) AU7281287A (enrdf_load_stackoverflow)
CA (1) CA1280404C (enrdf_load_stackoverflow)
ES (1) ES2004723A6 (enrdf_load_stackoverflow)
IN (1) IN169147B (enrdf_load_stackoverflow)
MX (1) MX169010B (enrdf_load_stackoverflow)
WO (1) WO1987005927A2 (enrdf_load_stackoverflow)
ZA (1) ZA872446B (enrdf_load_stackoverflow)

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WO1988004684A1 (en) * 1986-12-22 1988-06-30 The Lubrizol Corporation Lubricant composition
WO1988005810A1 (en) * 1987-01-30 1988-08-11 The Lubrizol Corporation Gear lubricant composition
WO1993024598A1 (en) * 1992-06-04 1993-12-09 The Lubrizol Corporation Functional fluid with borated epoxides, carboxylic solubilizers, zinc salts, calcium complexes and sulfurized compositions
EP0767236A1 (en) * 1995-10-04 1997-04-09 Ethyl Petroleum Additives Limited Friction modification of synthetic gear oils
EP0578435B1 (en) * 1992-07-09 1997-10-15 Ethyl Petroleum Additives Limited Friction modification of synthetic gear oils
EP1186647A1 (en) * 2000-09-01 2002-03-13 Minebea Co., Ltd. Moulded plastic products with anticorrosive lubricating coating
US6489271B1 (en) 1994-08-03 2002-12-03 The Lubrizol Corporation Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
US6617287B2 (en) 2001-10-22 2003-09-09 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
US6642187B1 (en) 1994-08-03 2003-11-04 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
WO2013148171A1 (en) 2012-03-26 2013-10-03 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
WO2013148146A1 (en) 2012-03-26 2013-10-03 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
WO2015017172A1 (en) 2013-07-31 2015-02-05 The Lubrizol Corporation Method of lubricating a transmission which includes a synchronizer with a non-metallic surface
JPWO2012165106A1 (ja) * 2011-05-27 2015-02-23 Ｊｘ日鉱日石エネルギー株式会社 潤滑油添加剤および潤滑油組成物

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CA2589358C (en) 2004-12-09 2015-01-27 The Lubrizol Corporation Process of preparation of an additive and its use
WO2014059277A1 (en) * 2012-10-12 2014-04-17 Basf Se Lubricant compositions comprising boroxines to improve fluoropolymer seal compatibility
JP6991249B2 (ja) * 2017-06-09 2022-02-10 ダウ グローバル テクノロジーズ エルエルシー スリップ剤を含有する多層フィルムおよびラミネート
CA3087248A1 (en) * 2018-02-28 2019-09-06 Chevron Oronite Company Llc Functional fluids lubricating oil compositions
CN111979028A (zh) * 2020-09-08 2020-11-24 定远县云森科技有限公司 一种低气味低腐蚀性极压抗磨剂及其制备方法

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US4344854A (en) * 1975-03-21 1982-08-17 The Lubrizol Corporation Sulfurized compositions
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CA1064463A (en) * 1975-03-21 1979-10-16 Kirk E. Davis Sulfurized compositions
BR7603218A (pt) * 1975-06-23 1977-05-24 Lubrizol Corp Composicao ultil como lubrificante e fluido atuante;e processo para provocar o entumescimento de vedacoes
US4031023A (en) * 1976-02-19 1977-06-21 The Lubrizol Corporation Lubricating compositions and methods utilizing hydroxy thioethers
US4172855A (en) * 1978-04-10 1979-10-30 Ethyl Corporation Lubricant
CA1188704A (en) * 1981-05-26 1985-06-11 Kirk E. Davis Boron-containing compositions useful as lubricant additives
AU549639B2 (en) * 1981-07-01 1986-02-06 Chevron Research Company Lubricating oil composition to improve fuel economy
EP0157969B2 (en) * 1984-04-05 2000-01-12 The Lubrizol Corporation Organo-borate compositions and their use in lubricants

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4792410A (en) * 1986-12-22 1988-12-20 The Lubrizol Corporation Lubricant composition suitable for manual transmission fluids
AU600791B2 (en) * 1986-12-22 1990-08-23 Lubrizol Corporation, The Lubricant composition
WO1988004684A1 (en) * 1986-12-22 1988-06-30 The Lubrizol Corporation Lubricant composition
WO1988005810A1 (en) * 1987-01-30 1988-08-11 The Lubrizol Corporation Gear lubricant composition
EP0501527A1 (en) * 1987-01-30 1992-09-02 The Lubrizol Corporation Gear lubricant composition
US5523005A (en) * 1987-01-30 1996-06-04 The Lubrizol Corporation Gear lubricant composition
WO1993024598A1 (en) * 1992-06-04 1993-12-09 The Lubrizol Corporation Functional fluid with borated epoxides, carboxylic solubilizers, zinc salts, calcium complexes and sulfurized compositions
EP0578435B1 (en) * 1992-07-09 1997-10-15 Ethyl Petroleum Additives Limited Friction modification of synthetic gear oils
US6489271B1 (en) 1994-08-03 2002-12-03 The Lubrizol Corporation Combination of a sulfur compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases
US6642187B1 (en) 1994-08-03 2003-11-04 The Lubrizol Corporation Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound
EP0767236A1 (en) * 1995-10-04 1997-04-09 Ethyl Petroleum Additives Limited Friction modification of synthetic gear oils
EP1186647A1 (en) * 2000-09-01 2002-03-13 Minebea Co., Ltd. Moulded plastic products with anticorrosive lubricating coating
US6703354B2 (en) 2000-09-01 2004-03-09 Minebea Co., Ltd. Anticorrosive lubricant composition for molded plastic products and molded plastic products with same applied thereto
US6617287B2 (en) 2001-10-22 2003-09-09 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
JPWO2012165106A1 (ja) * 2011-05-27 2015-02-23 Ｊｘ日鉱日石エネルギー株式会社 潤滑油添加剤および潤滑油組成物
EP2778216A4 (en) * 2011-05-27 2015-03-04 Jx Nippon Oil & Energy Corp ADDITION TO LUBRICATING OILS AND LUBRICATING OIL COMPOSITION
WO2013148171A1 (en) 2012-03-26 2013-10-03 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
WO2013148146A1 (en) 2012-03-26 2013-10-03 The Lubrizol Corporation Manual transmission lubricants with improved synchromesh performance
WO2015017172A1 (en) 2013-07-31 2015-02-05 The Lubrizol Corporation Method of lubricating a transmission which includes a synchronizer with a non-metallic surface
US10196581B2 (en) 2013-07-31 2019-02-05 The Lubrizol Corporation Method of lubricating a transmission which includes a synchronizer with a non-metallic surface

Also Published As

Publication number Publication date
WO1987005927A3 (en) 1988-03-24
CA1280404C (en) 1991-02-19
CN1018843B (zh) 1992-10-28
ES2004723A6 (es) 1989-02-01
IN169147B (enrdf_load_stackoverflow) 1991-09-07
MX169010B (es) 1993-06-17
AU7281287A (en) 1987-10-20
CN87102960A (zh) 1988-01-20
ZA872446B (en) 1987-11-25

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