EP1699910A2 - Sedimentarme reibungsmodifikatoren - Google Patents

Sedimentarme reibungsmodifikatoren

Info

Publication number
EP1699910A2
EP1699910A2 EP04811353A EP04811353A EP1699910A2 EP 1699910 A2 EP1699910 A2 EP 1699910A2 EP 04811353 A EP04811353 A EP 04811353A EP 04811353 A EP04811353 A EP 04811353A EP 1699910 A2 EP1699910 A2 EP 1699910A2
Authority
EP
European Patent Office
Prior art keywords
overbased
fatty acid
alkaline earth
sulfonate
reaction product
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04811353A
Other languages
English (en)
French (fr)
Inventor
Michael T. Costello
Igor Riff
Joseph A. Weaver, Jr.
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.)
Lanxess Solutions US Inc
Original Assignee
Chemtura 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
Application filed by Chemtura Corp filed Critical Chemtura Corp
Publication of EP1699910A2 publication Critical patent/EP1699910A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • 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
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/106—Naphthenic fractions
    • C10M2203/1065—Naphthenic fractions used as base material
    • 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
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/26—Overbased carboxylic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/046—Overbasedsulfonic acid salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • 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
    • C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/055—Particles related characteristics
    • C10N2020/06—Particles of special shape or size
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/52—Base number [TBN]
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation

Definitions

  • the present invention relates to friction modifiers for lubricant oils used, for example, in engines for motorized vehicles.
  • Friction modifiers for enhancing the lubricity of lubricant oils are known.
  • Typical friction modifiers include esters of glycerol and fatty acids, overbased carboxylates, and oxidized petroleum fractions.
  • detergent additives such as overbased calcium sulfonates.
  • a common problem which occurs when aging the lubricant oil is the formation of sediment.
  • sedimentation occurs in stocks of lubricant oils containing friction modifiers and detergent additive.
  • a sedimentation rate of a few percent can correspond to a thousand or more gallons of bottom sediment, which is clearly undesirable. What is needed is an additive for lubricant oils which provides a friction modifier and detergent, and which is characterized by a low sedimentation rate.
  • the additive mixture comprises: (a) an overbased alkaline earth metal sulfonate; and, (b) at least one friction modifier selected from the group consisting of an overbased alkaline earth carboxylate, the reaction product of an alkanolamine with a fatty acid or a fatty acid ester, the reaction product of thiodiglycol with a fatty acid or a fatty ester and the reaction product of a dialkylene glycol with a fatty acid or a fatty ester.
  • the additive mixture provides a lubricant oil composition having improved lubricity and exhibits less sedimentation.
  • FIG. 1 is a graph illustration the sedimentation results of Example 75; and, FIG. 2 is a graph illustrating the friction test results of Example 76.
  • Lubricating oil compositions used to lubricate the moving parts of engines, especially internal combustion engines contain base oil of lubricating viscosity, or a mixture of such oils, and additives used to improve the performance characteristics of the oil.
  • additives are used to improve detergency, reduce engine wear, to provide stability against heat and oxidation, to reduce oil consumption, to inhibit corrosion, to act as a dispersant, and reduce friction loss.
  • Some additives provide multiple benefits, such as a dispersant/viscosity modifier.
  • Other additives, while improving one characteristic of the lubricating oil have an adverse affect on other characteristics.
  • the present invention is a low sediment additive mixture for lubricant oils which comprises an overbased alkaline earth metal sulfonate with a selected friction modifier.
  • the additive mixture can be added to any type of lubricant oil including metal cutting and drawing oils, although motor oils are preferred.
  • the lubricant oils can be natural or synthetic. Natural oils include petroleum oils, solvent-treated, acid treated or hydrotreated mineral oils, coal oil and shale oil.
  • the lubricant oil can include saturated, olefinic unsaturated and aromatic components.
  • the lubricant oil can include hydrocarbon and/or non-hydrocarbon components such as fatty acids and fatty acid esters.
  • Overbased alkaline earth sulfonates are detergent compounds prepared by neutralizing a sulfonic acid with an excess of alkaline earth metal base (e.g., the hydroxides of magnesium, calcium or barium) so as to produce an overbased alkaline earth metal sulfonate with a total base number ("TBN") of greater than zero.
  • TBN total base number
  • the TBN is the amount of acid needed to neutralize all of the alkalinity of the overbased material, and can be determined according to ASTM D 2896.
  • a composition with a TBN of about 100 or less is considered to be a "low overbased material.”
  • a TBN of about 100 to 300 is characterized as “moderate overbasing.”
  • a composition with a TBN of over 300 is considered to be a "highly overbased” material.
  • the preferred overbased alkaline earth metal sulfonate is overbased calcium sulfonate having a TBN of above about 250, preferably above about 350, and more preferably 400 or higher. In one aspect of the invention it has been found that amorphous overbased calcium sulfonate is superior to crystalline calcium overbased sulfonate in terms of undesired sedimentation.
  • the amorphous overbased calcium sulfonate has a particle size of less than about 30 nm.
  • Crystalline overbased calcium sulfonates have a particle size above 30 nm, preferably 50-500 nm and more preferably 50-100 nm.
  • CalcinateTM C-300CS available from Crompton Corporation, is an example of a crystalline overbased calcium sulfonate.
  • a method for preparing highly overbased calcium sulfonate is described in U.S. Patent No. 6,444,625 B 1, which is herein incorporated by reference.
  • the lubricant composition also comprises a friction modifier to reduce the coefficient of friction.
  • the friction modifier and overbased calcium sulfonate can be combined and packaged with other additives such as antioxidants, dispersants andor defoamers, or other types of additives such as mentioned above.
  • Various friction modifiers can be used in the additive mixture.
  • Such friction modifiers include glycerol monoesters, overbased carboxylates, overbased tall oil fatty acids, the reaction product of an alkanolamine (e.g., triethanolamine (“TEA”) or diethanolamine) or a glycol (e.g., thiodiglycol, diethylene glycol) with a fatty acid or fatty ester, oxygenated petroleum fractions, alkoxylated allcylamine and the reaction products of glycols with fatty esters.
  • TAA triethanolamine
  • diethanolamine diethanolamine
  • glycol e.g., thiodiglycol, diethylene glycol
  • Glycerol monoesters useful as friction modifiers include, for example, glycerol esters of saturated or unsaturated C 8 to C 20 fatty acids such as glycerol monopalmitate, glycerol monostearate, glycerol monooleate, and the like.
  • Overbased carboxylates are known and are generally prepared by reacting an acidic material, normally an acidic gas such as SO 2 or CO 2) and most commonly carbon dioxide, with a mixture comprising a carboxylic acid and a stoichiometric excess of an alkaline base metal compound in a reaction medium, preferably with a promoter.
  • the base metal is preferably an alkaline earth metal such as magnesium, calcium or barium in the form of an oxide or hydroxide.
  • the carboxylic acid is preferably a saturated or unsaturated carboxylic acid having from about 8 to about 30 carbon atoms.
  • Useful carboxylic acids include, but are not limited to, caprylic acid, capric acid, lauric acid, myristic acid, myristoleic acid, decanoic acid, dodecanoic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, margaric acid, stearic acid, 12- hydroxystearic acid, oleic acid, ricinoleic acid, linoleic acid, arachidic acid, gadoleic acid, eicosadienoic acid, behenic acid, erucic acid, mixtures of any of these acids or their reactive equivalent.
  • overbased carboxylates include overbased calcium tallate and overbased barium tallate.
  • a reaction product of TEA and fatty ester suitable for use as a friction modifier is the reaction product of TEA and methyl oleate.
  • Other suitable friction modifiers include the reaction products of TEA with, for example, oleic acid, ricinoleic acid, isostearic acid, erucic acid, tall oil fatty acid (TOFA), mixed oleic/stearic acids, and iso-oleic acid.
  • Oxygenated petroleum fractions are known. Petroleum oxidates and methods for making them are disclosed in U.S. Patent No. 5,439,602, which is herein incorporated by reference.
  • Also suitable for use as friction modifiers are the reaction products of thiodiglycol with fatty acids or fatty esters (e.g., oleic acid, methyl oleate, etc.), and the reaction products of a dialkylene glycol (e.g., diethylene glycol, dipropylene glycol, etc.) with a fatty acid or fatty ester (e.g., oleic acid, methyl oleate, etc.).
  • a dialkylene glycol e.g., diethylene glycol, dipropylene glycol, etc.
  • a fatty acid or fatty ester e.g., oleic acid, methyl oleate, etc.
  • Particularly preferred as a friction modifier are the reaction products of TEA with fatty acids or fatty esters for both excellent lubricity and low sedimentation.
  • a preferred crystalline overbased calcium sulfonate is available from Crompton Corp. under the designation Calcinate C300CS and has a particle size of about 50-500 nm. Preferred particle size for a crystalline overbased calcium sulfonate ranges from about 50 rrm to about 100 nm.
  • the following Examples illustrate features of the invention. In one type of experiment, illustrated below in Examples 1-30 and 59-75, lubricant oils containing a selected overbased calcium sulfonate and a selected friction modifier were tested for sedimentation. In another type of experiment, exemplified in Examples 31-58 and 76, the lubricant oils containing combinations of selected overbased calcium sulfonates and fiiction modifiers were tested for friction reducing characteristics.
  • Examples 1-8 These examples are directed to a study of the sedimentation characteristics of various blends of overbased calcium sulfonate and selected friction modifiers.
  • Two types of overbased calcium sulfonates were individually tested.
  • CalcinateTM C300CS is a crystalline overbased calcium sulfonate having TBN of about 300 and a particle size of from about 50nm to about 100 nm, and is available from Crompton Corporation.
  • CalcinateTM C400CLR is an amorphous overbased calcium sulfonate available from Crompton Corporation having TBN of about 400 and a particle size of no more than about 30 nm.
  • Overbased calcium sulfonates were present in 10% concentrations.
  • the friction modifier included glycerol mono oleate ("GMO").
  • Polyisobutylene succinic anhydride having a molecular weight of about 1,050, was present in Examples 3, 4, and 7 as a dispersant.
  • the friction modifier was present in 1% concentrations when employed.
  • the lubricant oil stock was a severely hydrotreated naphthenic oil available from Ergon, ie. under the designation Hyprene HI 00.
  • Hyprene HI 00 is characterized by an API gravity (60° F) of24.6, a pour point of -50 °F, and an aniline point of 163° F.
  • Examples 9 to 16 Sedimentation experiments were conducted in the same manner as in Examples 1- 8 except that the friction modifiers tested were an oxidized petroleum fraction available under the designation Alox 165L from Lubrizol, an overbased calcium oleate, designated herein as "OCO", and GMO. The friction modifiers, when employed, were each present in 0.5% concentration. Examples 10 and 14 did not employ any friction modifiers. As can been seen from the results the amorphous overbased calcium sulfonate CalcinateTM C400CLR (Examples 13-16) was characterized by very low sedimentation percentages (typically about 0.001 to about 0.005) as opposed to the sedimentation percentages (0.11 to 0.50) for the CalcinateTM C300CS (Examples 9-12). The results of these experiments are set forth in Table 2.
  • Examples 17 to 28 Sedimentation experiments were conducted in a manner similar to Examples 9 to 16, except that the friction modifiers tested were OCO (overbased calcium oleate), Alox 302 (oxygenated petroleum fraction), an overbased barium tallate having 3% -10% barium and designated herein as "OBT", an overbased calcium tallate having 4%-10% calcium and designated herein as "OCT", and GMO (glycerol mono oleate). Examples 22 and 28 did not employ any friction modifier.
  • OCO overbased calcium oleate
  • Alox 302 oxygenated petroleum fraction
  • OHT overbased barium tallate having 3% -10% barium and designated herein as "OBT”
  • OCT overbased calcium tallate having 4%-10% calcium and designated herein as "OCT”
  • GMO glycol mono oleate
  • the amorphous overbased calcium sulfonate CalcinateTM C400CLR (Example 23-28) is characterized by much lower percentages of sedimentation as opposed to the sedimentation percentages for the crystalline overbased calcium sulfonate CalcinateTM C300CS (Examples 17-22).
  • the results of these experiments are set forth in Table 3.
  • Examples 31-44 These Examples are directed to the friction reducing characteristics of the lubricant oil blends.
  • the coefficient of friction for the selected blends was measured with a Cameron-Plint TE-77 high frequency friction test. The conditions are set forth below Upper specimen 6mm X 16mm Dowel EN 1A (BS 1804 Part 1 Grade 1, 220M07) Lower specimen Flat hardened ground NSOH BO1 Gauge Plate (RC 60/0.4 ⁇ m) Frequency 5 Hz Load (N) 50-100 Amplitude 15 mm Temperature Profile for Cameron Plint Test
  • Examples 45-58 These Examples were conducted in a manner similar to those of Examples 33 to 49 except that CalcinateTM C300CS and CalcinateTM C400CLR were compared on the basis of equal TBN rather than equal weight. The results are set forth in Table 6.
  • the total amount of sediments formed at the end of the 12 week period are reported in Table 7.
  • the blend of Calcinate C300CS plus lubricant oil but without a friction modifier was conducted to provide a baseline comparison and was recorded at 0.25%.
  • the mixed oleic/stearic glycol is available from Arizona Chemical Co. under the designation Uniflex 1803.
  • the friction modifiers of Examples 65-74 are the reaction products of the specified compounds. As can be seen the use of friction modifies comprising the reaction product of TEA with methyl oleate, tall oil fatty acid, oleic acid, isostearic acid and mixed oleic/stearic acids resulted in low sedimentation as compared with the baseline level of 0.25%. Also, the use of the reaction product of thiodiglycol and methyl oleate resulted in low sedimentation. Overbased alkaline earth carboxylates also provided low sedimentation.
  • Example 75 The sedimentation tests of Examples 59 to 74 were extended past the 12 week period to determine the nature of failure mode of separation.
  • the results of selected friction modifiers are shown in FIG. 1.
  • a comparison is made with friction modifier produced by the reaction of TEA with a monomeric fatty acid distillate obtained from the dimerization of tall oil fatty acid, such as a mixture of branched and straight chain fatty acids available from Arizona Chemical Co. under the designation CenturyTM D-1.
  • Also shown in FIG. 1 are the sedimentation test results of a friction modifier produced by the reaction of TEA with a mixture of C18 mon-unsaturated mostly methyl branched fatty acids, available from Arizona Chemical Co. under the designation CenturyTM Dl 164.
  • the results show an initial induction period of very low sedimentation followed by a catastrophic failure the sediment completely precipitates in a one week period forming a distinct layer.
  • the layer then continues to compact over the next 2 - 4 weeks and reduces the sediment volume, as can be seen from the TEA + ricinoleic acid, or diethylene glycol + methyl oleate tests.
  • the sediment layer forms more slowly after the induction period, but a flocculant material is observed in the supernatant liquid.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
EP04811353A 2003-12-09 2004-11-15 Sedimentarme reibungsmodifikatoren Withdrawn EP1699910A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/731,600 US20050124510A1 (en) 2003-12-09 2003-12-09 Low sediment friction modifiers
PCT/US2004/038625 WO2005061683A2 (en) 2003-12-09 2004-11-15 Low sediment friction modifiers

Publications (1)

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EP1699910A2 true EP1699910A2 (de) 2006-09-13

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US (1) US20050124510A1 (de)
EP (1) EP1699910A2 (de)
JP (1) JP4686475B2 (de)
CN (1) CN100482776C (de)
WO (1) WO2005061683A2 (de)

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US7422999B2 (en) * 2005-02-14 2008-09-09 The Lubrizol Corporation Overbased vaterite containing salt composition
US20090048129A1 (en) * 2006-01-31 2009-02-19 Nissan Motor Co., Ltd. Nanoparticle-containing lubricating oil compositions
CN101336286B (zh) * 2006-01-31 2013-01-02 日产自动车株式会社 含有纳米颗粒的润滑油组合物
US8114822B2 (en) * 2006-10-24 2012-02-14 Chemtura Corporation Soluble oil containing overbased sulfonate additives
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WO2015034091A1 (ja) * 2013-09-09 2015-03-12 出光興産株式会社 変速機油
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JP4686475B2 (ja) 2011-05-25
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JP2007514038A (ja) 2007-05-31
CN1890354A (zh) 2007-01-03
CN100482776C (zh) 2009-04-29

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