USRE38929E1 - Lubricant containing molybdenum compound and secondary diarylamine - Google Patents
Lubricant containing molybdenum compound and secondary diarylamine Download PDFInfo
- Publication number
- USRE38929E1 USRE38929E1 US09/604,285 US60428500A USRE38929E US RE38929 E1 USRE38929 E1 US RE38929E1 US 60428500 A US60428500 A US 60428500A US RE38929 E USRE38929 E US RE38929E
- Authority
- US
- United States
- Prior art keywords
- molybdenum
- lubricating composition
- oil soluble
- acid
- oil
- 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.)
- Expired - Lifetime
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- 0 [1*]N([2*])[H] Chemical compound [1*]N([2*])[H] 0.000 description 6
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- 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
- C10M141/12—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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- 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
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- C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/024—Propene
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/026—Butene
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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- 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
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- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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Definitions
- This invention relates to lubricating oil compositions, their method of preparation, and use. More specifically this invention relates to lubricating oil compositions which contain a molybdenum compound and a secondary diarylamine wherein the molybdenum compound is substantially free of active sulfur. The use of both the molybdenum and amine within certain concentrations provide improved oxidation control and friction modifier performance to lubricating oil compositions.
- the lubricating oil compositions of this invention are particularly useful as crankcase lubricants.
- Lubricating oils as used in the internal combustion engines of automobiles or trucks are subjected to a demanding environment during use. This environment results in the oil suffering oxidation which is catalyzed by the presence of impurities in the oil such as iron compounds and is also promoted by the elevated temperatures of the oil during use. This oxidation of lubrication oils during use is usually controlled to some extent by the use of antioxidant additives which may extend the useful life of the oil, particularly by reducing or preventing unacceptable viscosity increases.
- molybdenum acts synergistically with secondary diarylamines to provide significant improvement in oxidation control.
- the molybdenum compounds also act as friction modifiers to provide substantial fuel economy performance.
- Lubricant compositions containing various molybdenum compounds and aromatic amines have been used in lubricating oils.
- Such compositions include active sulfur or phosphorus as part of the molybdenum compound, use additional metallic additives, various amine additives which are different from those used in this invention, and/or have concentrations of molybdenum and amine which do not show the synergistic results obtained by this invention.
- U.S. Pat. No. 4,394,279 of Jul. 19, 1983 to L. de Vries et al. discloses an antioxidant additive combination for lubrication oils prepared by combining (a) an active sulfur containing molybdenum compound prepared by reacting an acidic molybdenum compound, a basic nitrogen compound and carbon disulfide with (b) an aromatic amine compound.
- U.S. Pat. No. 4,832,857 of May 23, 1989 to Amoco Corp discloses a process for preparation of overbased molybdenum alkaline earth metal and alkali metal dispersions for use in lubricating oil compositions.
- WO95/07962 of Mar. 23, 1995 to A. Richie et al. discloses a crankcase lubricant composition for use in automobile or trunk engines which contains copper, molybdenum, and aromatic amines.
- this publication recites a very broad range of concentrations of amine used with the molybdenum in the examples of that publication is well outside the range which this invention has found to be synergistic.
- many of the molybdenum compounds of this reference contain active sulphur, phosphorus, and other elements and the amines include compounds such as primary amines which were not found synergistic with the molybdenum carboxylates of this invention.
- WO95/07963 of 23 Mar. 1995 to H. Shaub discloses highly sulfurized molybdenum compounds and various secondary aromatic amines having at least one aromatic group for producing a synergistic antioxidant effect when used as an antioxidant additive for lubricating oils. Again the molybdenum compounds contain active sulfur.
- WO95/07966 of 23 Mar. 1995 to J. Atherton et al. discloses engine oil lubricants of various molybdenum compounds including that of some with active sulfur, certain organo-phosphorus compounds, an aminic antioxidant and a phenolic antioxidant within certain proportions.
- this invention is directed to a lubricating composition
- a lubricating composition comprising (a) a major amount of lubrication oil, (b) an oil soluble molybdenum compound substantially free of active sulfur which provides about 100 to 450 parts per million of molybdenum, and (c) about 750 to 5,000 parts per million (ppm) of an oil soluble secondary diarylamine.
- the invention is directed to a method for improving the antioxidancy and friction properties of a lubricant by incorporating in the lubricant a molybdenum compound which is substantially free of active sulfur and a secondary diarylamine in the above described concentrations.
- the invention is directed to a lubrication oil concentrate comprising a solvent and a combination of from about 2.5 to 90 percent by weight of an oil soluble molybdenum compound which is substantially free of active sulfur and an oil soluble secondary diarylamine wherein the weight ratio of molybdenum from the molybdenum compound to the diarylamine in the concentration is from about 0.020 to 0.60 parts of molybdenum for each part of amine.
- the invention is directed to a lubricating composition prepared by mixing 100 to 450 parts per million of oil soluble molybdenum compound substantially free of active sulfur and 750 and 5,000 parts of a secondary diaryl amine in a lubricating composition.
- the invention is directed to a lubrication oil concentrate prepared by dissolving in about 10 to 97.5 parts of a solvent a total of 2.5 to 90 parts of an oil soluble molybdenum compound substantially free of active sulfur and an oil soluble secondary diaryl amine.
- the molybdenum compound used in the various compositions and methods of this invention is substantially free of sulfur.
- compositions of this invention have various uses as lubricants such as for automotive and trunk crankcase lubricants as well as transmission lubricants.
- a key advantage of this invention is the multifunctional nature of the molybdenum/diarylamine combination and the relatively low treat levels required for a performance benefit.
- This additive combination provides both oxidation control and friction control to the oil. This reduces the need for supplemental oxidation protection and frictional properties and should reduce the overall cost of the entire additive package. Further cost reduction is gained by the low treat levels employed.
- the molybdenum compound used in this invention can be any molybdenum compound which is soluble in the lubricant or formulated lubricant package and is substantially free of active sulfur.
- soluble or “oil soluble” is meant that the compound is oil soluble or solubilized under normal blending conditions into the lubrication oil or concentrate thereof.
- Active sulfur is sulfur which is not fully oxidized. Active sulfur further oxidizes and becomes more acidic in the oil upon use.
- sulfur such as divalent sulfur is active sulfur whereas the sulfur in a sulfonate group is fully oxidized and thus non-active sulfur. It is preferred however that the molybdenum compound be substantially free of all sulfur.
- the molybdenum compound contains less than about 0.5% by weight of the material in question, e.g., active sulfur which is generally an insufficient amount to add significantly to corrosion.
- the sulfur content of some commercially available molybdenum compounds can often have as much as about 1,000 ppm of sulfur as a contaminant and occasionally there can be as much as 2,000 ppm of the active sulfur. Such small amounts often come from contamination is processing the various ingredients involved.
- alkphenyl or “alkaryl” we mean a phenyl or aryl group, respectively, which contains an alkyl substituent.
- a molybdenum source such as ammonium molybdates, alkali and alkaline earth metal molybdates, molybdenum trioxide, and molybdenum acetylacetonates and an active hydrogen compound such as alcohols and polyols, primary and secondary amines and polyamines, phenols, ketones, anilines, etc.
- an active hydrogen compound such as alcohols and polyols, primary and secondary amines and polyamines, phenols, ketones, anilines,
- Molybdenum salts such as the carboxylates are a preferred group of molybdenum compounds.
- the molybdenum salts used in this invention may be completely dehydrated (complete removal of water during preparation), or partially dehydrated. They may be salts of the same anion or mixed salts, meaning that they are formed from more than one type of acid.
- suitable anions there can be mentioned chloride, carboxylate, nitrate, sulfonate, or any other anion.
- the molybdenum carboxylates may be derived from any organic carboxylic acid.
- the molybdenum carboxylate is preferably that of a monocarboxylic acid such as that having from about 4 to 30 carbon atoms.
- Such acids can be hydrocarbon aliphatic, alicyclic, or aromatic carboxylic acids.
- Monocarboxylic acids such as those of aliphatic acids having about 4 to 18 carbon atoms are preferred, particularly those having an alkyl group of about 6 to 18 carbon atoms.
- the alicyclic acids may generally contain from 4 to 12 carbon atoms.
- the aromatic acids may generally contain one or two fused rings and contain from 7 to 14 carbon atoms wherein the carboxyl group may or may not be attached to the ring.
- the carboxylic acid can be a saturated or unsaturated fatty acid having from about 4 to 18 carbon atoms.
- carboxylic acids that may be used m prepare the molybdenum carboxylates include: butyric acid; valeric acid; caproic acid heptanoic acid; cyclohexanecarboxylic acid; cyclodecanoic acid; naphthenic acid; phenyl acetic acid; 2-methylhexanoic acid; 2-ethylhexanoic acid; suberic acid; octanoic acid; nonanoic acid; decanoic acid; undecanoic acid; lauric acid, tridecanoic acid; myristic acid; pentadecanoic acid; palmitic acid; linolenic acid; heptadecanoic acid; stearic acid; oleic acid; nonadecanoic acid; eicosanoic acid; heneicosanoic acid; do
- 3,578,690 prepares its molybdenum carboxylates by reacting molybdenum oxide, molybdenum halide, alkali earth molybdate, alkaline earth molybdate, ammonium molybdate or mixtures of molybdenum sources with carboxylic acids at elevated temperatures and with removal of water.
- composition of the oil soluble molybdenum carboxylates can vary. Most of the literature refers to these compounds as molybdenum carboxylates. They have also been referred to as molybdenum carboxylate salts, molybdenyl (Mo O 2 2+ ) carboxylates and molybdenyl carboxylate salts, molybdenum carboxylic acid salts, and molybdenum salts of carboxylic acids.
- the concentration of the molybdenum from the molybdenum compound in the lubricant composition can vary depending upon the customer's requirements and applications.
- the actual amount of molybdenum added is based on the desired final molybdenum level in the lubricating composition. From about 100 to 450 parts per million of molybdenum are used in this invention based on the weight of the lubricating oil composition which may be formulated to contain additional additives and preferably about 100 to 250 parts per million of molybdenum and particularly 125 to 250 ppm are used based on the weight of the lubricating oil composition.
- the quantity of additive e.g. molybdenum carboxylate to provide molybdenum, is based on the total weight of the formulated or unformulated lubricating oil composition.
- the secondary diarylamines are well known antioxidants and there is no particular restriction on the type of secondary diarylamine used in the invention.
- the secondary diarylamine antioxidant has the general formula: wherein R 1 and R 2 each independently represents a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms.
- R 1 and R 2 each independently represents a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms.
- substituents for the aryl there can be mentioned aliphatic hydrocarbon groups such as alkyl having from about 1 to 20 carbon atoms, hydroxy, carboxyl or nitro, e.g., an alkaryl group having from 7 to 20 carbon atoms in the alkyl group.
- the aryl is preferably substituted or unsubstituted phenyl or naphthyl, particularly wherein one or both of the aryl groups are substituted with an alkyl such as one having from 4 to 18 carbon atoms. It is further preferred that both aryl groups be substituted, e.g. alkyl substituted phenyl.
- the secondary diarylamines used in this invention can be of a structure other than that shown in the above formula which shows but one nitrogen atom in the molecule.
- the secondary diarylamine can be of a different structure provided that at least one nitrogen has 2 aryl groups attached thereto, e.g., as in the case of various diamines having a secondary nitrogen atom as well as two aryls on one of the nitrogens.
- the secondary diarylamines used in this invention preferably have antioxidant properties in lubricating oils, even in the absence of the molybdenum compound.
- the secondary diarylamines used in this invention should be soluble in the formulated crankcase oil package.
- examples of some secondary diarylamines that may be used in this invention include: diphenyl amine; various alkylated diphenylamines, 3-hydroxydiphenylamine; N-phenyl-1,2-phenylenediamine; N-phenyl-1,4-phenylenediamine; dibutyldiphenylamine; dioctyldiphenylamine; dinonyldiphenylamine; phenyl-alpha-naphthylamine; phenyl-beta-naphthylamine; diheptyldiphenylamine; and p-oriented styrenated diphenylamine.
- the concentration of the secondary diarylamine in the lubricating composition can vary depending upon the customer's requirements and applications.
- a practical diarylamine use range in the lubricating composition is from about 750 parts per million to 5,000 parts per million (i.e. 0.075 to 0.5 wt %), preferably the concentration is from 1,000 to 4,000 parts per million (ppm) and particularly from about 1,200 to 3,000 ppm by weight. Quantities of less than 750 ppm have little or minimal effectiveness whereas quantities larger than 5,000 ppm are not economical.
- the quantity of molybdenum is relation to the quantity of the secondary amine should be within a certain ratio.
- the quantity of molybdenum should be about 0.020 to 0.6 parts by weight for each part by weight of the amine in the lubricating oil composition.
- this ratio will be from about 0.040 to 0.40 parts of the molybdenum per part of the amine and particularly about 0.05 to 0.3 parts of the molybdenum per part of the amine.
- the total quantity of molybdenum and amine can be provided by one or more than one molybdenum or amine compound.
- the composition of the lubricant oil can vary significantly based on the customer and specific application.
- the oil is a formulated oil which is composed of between 75 and 95 wt % of a mineral lubrication oil, between 0 and 10 wt % of a polymeric viscosity index improver, and between about 5 and 15 wt % (weight percent) of an additive package.
- the additive package generally contains the following components:
- the lubrication oil component of this invention may be selected from any of the synthetic or natural oils used as lubricants such as that for crankcase lubrication oils for spark-ignited and compression-ignited internal combustion engines, for example automobile and truck engines, marine, and railroad diesel engines.
- Synthetic base oils include alkyl esters of dicarboxylic acids, polyglycols and alcohols, poly-alpha-olefins, including polybutenes, alkyl benzenes, organic esters of phosphoric acids, and polysilicone oils.
- Natural base oils include mineral lubrication oils which may vary widely as to their crude source, e.g., as to whether they are paraffinic, naphthenic, or mixed paraffinic-naphthenic.
- the lubrication oil base stock conveniently has a viscosity of about 2.5 to about 15 cSt or mm 2/ s and preferably about 2.5 to about 11 cSt or mm 2/ s at 100° C.
- a polymeric viscosity index improver (VII) component may be used in this invention and such component may be selected from any of the known viscosity index improvers.
- the function of the VII is to reduce the rate of change of viscosity with temperature, i.e. they cause minimal increase in engine oil viscosity at low temperature but considerable increase at high temperature.
- examples of viscosity index improvers include polyisobutylenes, polymethacrylates, ethylene/propylene copolymers, polyacrylates, styrene/maleic ester copolymers, and hydrogenated styrene/butadiene copolymers.
- supplemental additives that perform specific functions not provided by the main components.
- additional additives include, pour point depressants, corrosion inhibitors, rust inhibitors, foam inhibitors and supplemental friction modifiers.
- the lubricating oil compositions of this invention can be made by adding the molybdenum additive and the secondary diarylamine additive in a lubrication oil composition.
- the composition can also contain additional additives such as dispersants, detergents, zinc dihydrocarbyl dithiophosphates, and still additional antioxidants.
- additional additives such as dispersants, detergents, zinc dihydrocarbyl dithiophosphates, and still additional antioxidants.
- the method or order of component addition is not critical.
- the combination of molybdenum and amine additives can be added to the lubrication oil as a concentrate with or without such concentrate containing the remaining additives.
- the lubricating oil concentrate will comprise a solvent and from about 2.5 to 90 weight percent (wt %) and preferably 5 to 75 wt % of the combination of the molybdenum additive and amine additive of this invention.
- the solvent may be that of hydrocarbon oils, e.g., mineral lubrication oil or a synthetic oil.
- the ratio of molybdenum to amine in the concentrate composition is from about 0.02 to 0.6 parts of molybdenum per part of amine and preferably from about 0.04 to 0.4 parts of molybdenum for each part of the amine by weight.
- the concentrate may contain additional additives as is conventional in the art, e.g., dispersants, detergents, and zinc dihydrocarbyl dithiophosphates.
- the molybdenum compound in this invention is preferably substantially free of phosphorus and substantially free of active sulfur and it is particularly preferred to have the molybdenum compound substantially free of sulfur whether active or otherwise.
- the following example shows the antioxidant synergism that exist,; when molybdenum naphthenate and a diphenylamine are formulated into an SAE Grade 5W-30 type motor oil.
- the example also shows that this antioxidant behavior is unique when compared to other metals.
- the DSC cell was pressurized with 500 psi air and programmed with the following heating sequence: (1) jump from ambient to 165° C., (2) jump from 165° C. to 175° C. at 2 C/min. (3) isothermal at 175° C.
- the oil samples were held at 175° C. until an exothermic release of heat was observed.
- the exothermic release of heat marks the oxidation reaction.
- the time from the start of the experiment to the exothermic release of heat is called the oxidation induction time and is a measure of the oxidation stability of the oil (i.e. the longer the oxidation induction time the greater the oxidative stability of the oil). All oils are evaluated in duplicate and the results averaged.
- the other metals show very little effect, or a negative effect, on the oxidative stabilty of the oil.
- the other metals show no interaction effect, or a negative interaction effect, with the diphenylamine.
- Ce Nap is cesium naphthenate
- Co Nap is cobalt naphthenate
- Ni Oct is nickel octanoate
- Mo Nap is molybdenum naphthenate.
- concentration of metallic additives is expressed in parts per million of the metal.
- DPA is dinonyldiphenylamine which is expressed in percent by weight, e.g. 0.1 wt % being 1,000 ppm;
- Induction Time is the DSC Induction Time in minutes as an average.
- concentration of the molybdenum naphthenate is expressed in ppm of molybdenum whereas the concentration of the N-680 Amine is expressed in weight percent, i.e. 0.1 wt % is equal to 1,000 ppm.
- the oxidation induction time by PDSC in minutes is in the column headed as “Induction Time”.
- the OIT expected response in minutes is in the column under “Expected Time”; the viscosity increase from 72 hour HOOT (%) is an average of duplicate runs and is under the column headed “Viscosity Increase”.
- Molybdenum naphthenate and a variety of amines were blended into an SAE Grade 5W-30 type motor oil (formulated crankcase oil as described in Example 2) as shown in Table III and as further described below.
- the only additional antioxidant in these blends was the zinc dialkyl dithiophosphate.
- the oxidation stability of these oils was measured by pressurized differential scanning calorimetry (PDSC) as described in Example 1. These oils were also subjected to the hot oil oxidation test described in Example 2.
- Example 3 The results of the tests of Example 3 are shown in Table III.
- Table III the first column is the test number involved.
- the column headed “A” shows the concentration of molybdenum naphthenate expressed in ppm of molybdenum.
- the remaining columns “B” through “J” show concentrations in weight percent wherein column “B” is that of dinonyl diphenylamine; column “C” is an alkylated diphenylamine trade named Naugalube 680, from Uniroyal Chemical Company; “D” is phenyl-alpha-naphthylamine; “E” is disecbutyl phenylenediamine; “F” is 4-tetradecylaniline; “G” is 2,5-di-t-butylaniline; “H” is 2,6-diisopropyl aniline; “I” is di-n-decylamine; and “J” is that of process oil.
- Table IIIA wherein for each of the
- Mo-Oct is molybdenum octoate
- N-680 is alkylated diphenylamine
- t-Bu is t-butylphenols
- PO is process oil.
- Molybdenum 2-ethylhexanoate containing 13.0 wt % molybdenum and alkylated diphenylamine.
- Naugalube 680 from Uniroyal Chemical Company, were blended into an SAE grade 5W-30 motor oil as shown in Table V below.
- the control 5W-30 motor oil contained the following additives:
- the oxidative stability of these oils was measured by using the following Hot Oil Oxidation Test: Into 25 g of each motor oil was blended 0.8 g of catalyst mixture containing 5.55 wt % Iron (III) Naphthenate (6 wt % Fe content) and 94.45 wt % xylenes. Dry air was blown through the oil at a rate of 10 L/h (liters per hour) while maintaining the temperature at 160° C. for a period of 64 hours. The oil was cooled and the percent change in viscosity between the new oil and the oxidized oil was determined at 40° C. The lower percent change in viscosity for an oil is an indication of less oil degradation and thus better oxidation control by the additives.
- the abbreviations “% visc Incr” in Table V relates to percent viscosity increase. All oils were evaluated in duplicate and the results averaged. The results are found in Table V.
- a sample of molybdenum octoate was diluted with paraffin oil, blended at 50° C. for 1 hour and filtered using a pressure filtration apparatus.
- the molybdenum content of the filtered oil was determined to be 2.91 wt %
- a series of lubrication formulations in accordance with this invention were tested in the Sequence IIIE engine test.
- the IIIE test uses a 231 CID (3.8 liter) Buick V-6 engine at high speed (3,000 rpm) and a very high oil temperature of 149° C. for 64 hours. This test is used to evaluate an engine oil's ability to minimize oxidation, thickening, sludge, varnish, deposits, and wear.
- the formulations contained 7.0 wt % viscosity index improver, 7.0 wt % ashless dispersant, 1.1 wt % ZDDP, 1.4 wt % detergents, 0.5 wt % supplemental additives, with the remainder being mineral oil.
- the molybdenum source in formulation C is molybdenum 2-ethylhexanoate available from OM Group, TVTM indicates that the oils viscosity was too viscous to measure and represents a severe failing result in the IIIE engine.
- Some of the abbreviations used in the below Table VII are as follows: “% Vise, Inc.@ 64 h” means percent viscosity increase in 64 hours; “AE Sludge” is average engine sludge rating; “APS Varnish” is average piston skirt varnish; “ORL Deposit” is oil ring land deposit; “AC Wear” is average cam wear; MC Wear is maximum cam wear; and “L” is liters.
- the following example shows antioxidant synergism between molybdenum and a diarylamine wherein the molybdenum compound is not a carboxylate.
- Molyvan 855 a sulfur and phosphorus free organic amide molybdenum complex supplied by R. T. Vanderbilt Company, Inc. (CAS Reg. No. 64742-52-5), alkylated diphenylamine Naugalube 680, from Uniroyal Chemical Company, and process oil were blended into an SAE Grade 5W-30 type motor oil as shown in Table IX below.
- the formulated oil used in this example was the same as that used in Example 1.
- the only additional antioxidant in these blends was the zinc dialkyldithiophosphate.
- the oxidation stability of these oils was measured by pressurized differential scanning calorimetry (PDSC) as described in Example 1.
- the expected values are what one would observe if there were no synergism between the Molyvan 855 and the alkylated diphenylamine, i.e. the additives act independently of each other.
- the much larger measured OIT values versus the expected values clearly show the organic amide molybdenum complex/diphenylamine synergism.
Abstract
Description
-
- 1. Glycol molybdate complexes as described by Price et al in U.S. Pat. No. 3,285,942 of Nov. 15, 1966;
- 2. Overbased alkali metal and alkaline earth metal sulfonates, phenates and salicylate compositions containing molybdenum such as those disclosed and claimed by Hunt et al in U.S. Pat. No. 4,832,857 of May 23, 1988 which is incorporated herein by reference in its entirety. The sulfur in the compounds of Hunt et al does not provide antioxidant protection in the oil, i.e., the activity of the sulfur is deactivated by the overbased nature of these additives. Indeed, it is generally known that the molybdenum-free sulfonates act as pro-degradants in the oil (Atmospheric Oxidation and Stabilization” by T. Colclough page 49). The main purpose for adding the molybdenum-free overbased sulfonates is to provide detergency. When used in combination with diarylamines, the overbased molybdenum sulfonates such as those described by Hunt et al are expected to provide synergistic antioxidant protection to lubricants. The molybdenum containing overbased alkaline earth metal and alkali metal sulfonates, phenates, and salicylates are prepared by a process which comprises:
- (a) introducing into a reaction zone a compound selected from the group consisting of a sulfonate, a phenate, and a salicylate wherein said compound is an overbased alkaline earth or alkali metal compound; (b) adding to said reaction zone a solvent to solubilize said compound and to form a mixture A; (c) heating said mixture A to an elevated temperature of 120° F. or less; (d) preparing an aqueous solution of a molybdenum compound at a temperature of 120° F. or less; (e) adding said aqueous solution of said molybdenum compound to said mixture A with stirring during a period of about 15 minutes or less to form a mixture B; (f) adding said mixture B containing said molybdenum compound to a non-polar compound at a temperature of 220° F. or greater within a period of up to 40 minutes wherein resulting mixture C during said addition is at a temperature of at least 220° F.; (g) driving off said water and said non-polar compound as overhead by increasing temperature of said mixture C containing said molybdenum compound to about 240° F. to about 300° F. to obtain a water-free composition; (h) adding additional quantity of a non-polar compound to said water-free composition to dilute said composition to clarify said composition by filtration or centrifugation; (i) heating said clarified composition to a temperature of from about 300° F. to about 400° F. to remove solvent and said non-polar compound and to recover product comprising an overbased molybdenum-containing alkaline earth metal or alkali metal compound.
- 3. Molybdenum complexes prepared by reacting a fatty oil, a diethanolamine and a molybdenum source as described by Rowan et al in U.S. Pat. No. 4,889,647 of Dec. 26, 1989;
- 4. Molybdenum containing compounds prepared from fatty acids and 2-(2-aminoethyl)aminoethanol as described by Karol in U.S. Pat. No. 5,137,647 of Aug. 11, 1992;
- 5. Overbased molybdenum complexes prepared from amines, diamines, alkoxylated amines, glycols and polyols as described by Gallo et in U.S. Pat. No. 5,143,633 of Sep. 1, 1992; and
- 6. 2,4-Heteroatom substituted-molybdena-3,3-dioxacycloalkanes as described by Karol in U.S. Pat. No. 5,412,130 of May 2, 1995.
wherein R1 and R2 each independently represents a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms. Illustrative of substituents for the aryl there can be mentioned aliphatic hydrocarbon groups such as alkyl having from about 1 to 20 carbon atoms, hydroxy, carboxyl or nitro, e.g., an alkaryl group having from 7 to 20 carbon atoms in the alkyl group. The aryl is preferably substituted or unsubstituted phenyl or naphthyl, particularly wherein one or both of the aryl groups are substituted with an alkyl such as one having from 4 to 18 carbon atoms. It is further preferred that both aryl groups be substituted, e.g. alkyl substituted phenyl.
- (a). Dispersants. The dispersants are nonmetallic additives containing nitrogen or oxygen polar groups attached to a high molecular weight hydrocarbon chain. The hydrocarbon chain provides solubility on the hydrocarbon base stocks. The dispersant functions to keep oil degradation products suspended in the oil. Examples of commonly used dispersants include copolymers such as polymethacrylates and styrenemaleinic ester copolymers, substituted succinamides, polyamine succinamides, polyhydroxy succinic esters, substituted mannich bases, and substituted triazoles. Generally, the dispersant is present in the finished oil between about 4.0 and 8.5 wt %.
- (b). Detergents. The detergents are metallic additives containing charged polar groups, such as sulfonates or carboxylates, with aliphatic, cycloaliphatic, or alkylaromatic chains, and several metal ions. The detergents function by lifting deposits from the various surfaces of the engine. Examples of commonly used detergents include neutral and overbased alkali and alkaline earth metal sulfonates, neutral and overbased alkali and alkaline earth metal phenates, sulfurized phenates, overbased alkaline earth salicylates, phosphonates, thiopyrophosphonate, and thiophosphonates. Generally, the detergents are present in the finished oil between about 1.0 and 2.5 wt %.
- (c). ZDDP's. The ZDDP's (zinc dihydrocarbyl dithiophosphates) are the most commonly used antiwear additives in formulated lubricants. These additives function by reaction with the metal surface to form a new surface active compound which itself is deformed and thus protects the original engine surface. Other examples of anti-wear additives include tricresol phosphate, dilauryl phosphate, sulfurized terpenes and sulfurized fats. The ZDDP's also function as antioxidants. Generally, the ZDDP is present in the finished oil between about 1.0 and 1.5 wt %, although when used, they can be used at substantially lower concentrations, e.g., 0.5 wt %. It is desirable from environmental concerns to have lower levels of ZDDP.
- (d). Antioxidants. In molybdenum-free oils other antioxidants in addition to the zinc dihydrocarbyl dithiophosphates are used to protect the oil from oxidative degradation. The amount of supplemental antioxidant will vary depending on the oxidative stability of the base stock. Typical treat levels in finished oils can vary from about 1.0 to 2.5 wt %. The supplementary antioxidants that are generally used include hindered phenols, hindered bisphenols, sulfurized phenols, alkylated diphenylamines, sulfurized olefins, alkyl sulfides and disulfides, dialkyl dithiocarbamates, and phenothiazines. The inclusion of molybdenum carboxylates with diphenylamines removes the need for these supplementary antioxidants. However, a supplementary antioxidant may be included in oils that are less oxidatively stable or in oils that are subjected to unusually severe conditions.
-
- 1. The improved oxidative stability of the oil is predominantly due to the presence of molybdenum naphthenate and diphenylamine.
- 2. There is a strong interaction effect, i.e. synergism, between molybdenum naphthenate and the diphenylamine.
TABLE I |
PDSC Induction Times for Motor Oil Blends |
Concentration of Additives In SAE Grade 5W-30 Type Motor Oil* |
Oil | Cc | Co | Ni | Mo | Process | Induction | |
No. | Nap | Nap | Oct | Nap | DPA | Oil Wt. % | Time |
1 | 0 | 0 | 0 | 0 | 0.10 | 1.50 | 41.8 |
2 | 200 | 0 | 0 | 0 | 0.00 | 1.27 | 16.5 |
3 | 0 | 200 | 0 | 0 | 0.00 | 1.27 | 26.4 |
4 | 200 | 200 | 0 | 0 | 0.10 | 0.83 | 26.5 |
5 | 0 | 0 | 200 | 0 | 0.00 | 1.35 | 16.1 |
6 | 200 | 0 | 200 | 0 | 0.10 | 0.92 | 28.1 |
7 | 0 | 200 | 200 | 0 | 0.10 | 0.92 | 33.5 |
8 | 200 | 200 | 200 | 0 | 0.00 | 0.68 | 22.7 |
9 | 0 | 0 | 0 | 200 | 0.00 | 1.27 | 24.7 |
10 | 200 | 0 | 0 | 200 | 0.10 | 0.83 | 60.1 |
11 | 0 | 200 | 0 | 200 | 0.10 | 0.83 | 62.5 |
12 | 200 | 200 | 0 | 200 | 0.00 | 0.60 | 34.6 |
13 | 0 | 0 | 200 | 200 | 0.10 | 0.92 | 72.4 |
14 | 200 | 0 | 200 | 200 | 0.00 | 0.68 | 26.0 |
15 | 0 | 200 | 200 | 200 | 0.00 | 0.68 | 40.9 |
16 | 200 | 200 | 200 | 200 | 0.10 | 0.25 | 54.2 |
*A formulated crankcase oil containing 83.2 wt % base oil, 6.2 wt % polymeric viscosity index improver, 6.9 wt % ashless dispersant, 2.1 wt % calcium, sodium & magnesium overbased & neutral detergents, and 1.2 wt % zinc dialkyldithiophosphate. |
TABLE IA |
Main Effects and Interaction Effects On PDSC Oxidation Induction Time |
Main Effect | Interaction Effect | |||
Factors and Interactions | (minutes) | (minutes) | ||
Cc Nap | −6.2 | |||
Co Nap | 2.0 | |||
Ni Oct | 0.1 | |||
Mo Nap | 20.5 | |||
DPA | 21.4 | |||
Cc Nap with Co Nap | −0.2 | |||
Cc Nap with Ni Oct | −1.8 | |||
Cc Nap with Mo Nap | −0.2 | |||
Co Nap with Ni Oct | 0.2 | |||
Co Nap with Mo Nap | 0.3 | |||
Ni Oct with Mo Nap | 2.8 | |||
Mo Nap with DPA | 9.4 | |||
Ni Oct with DPA | −0.8 | |||
Co Nap with DPA | −8.4 | |||
Cc Nap with DPA | −4.1 | |||
TABLE II |
Oxidative Stability of Motor Oil Blends* |
by PDSC and the Hot Oil Oxidation Test |
Concentration | ||||||
of Additives | Process | Induc- | ||||
Oil | Mo Nap | N-680 | Oil | tion | Expected | Viscosity |
# | (As ppm Mo) | Wt % | Wt % | Time | Time | Increase |
1 | 0 | 0.000 | 1.25 | 28.4 | 28.4 | 303.18 |
2 | 125 | 0.000 | 1.04 | 35.1 | 35.1 | 671.48 |
3 | 250 | 0.000 | 0.83 | 33.0 | 33.0 | 362.22 |
4 | 0 | 0.075 | 1.18 | 44.9 | 44.9 | 44.64 |
5 | 125 | 0.075 | 0.97 | 63.5 | 51.6 | 36.93 |
6 | 250 | 0.075 | 0.76 | 73.0 | 49.5 | 66.10 |
7 | 0 | 0.150 | 1.10 | 62.5 | 62.5 | 31.61 |
8 | 125 | 0.150 | 0.89 | 107.8 | 69.2 | 11.93 |
9 | 250 | 0.150 | 0.68 | 108.7 | 67.1 | 10.02 |
* A formulated crankcase oil containing 83.2 wt % base oil, 6.2 wt % polymeric viscosity index improver, 6.9 wt % ashless dispersant, 2.1 wt % calcium, sodium, and magnesium overbased and neutral detergents, and 1.2 wt % zinc dialkyldithiophosphate. |
TABLE III |
Oxidation of Motor Oils Containing Molybdenum Naphthenates and Amines |
Concentration of additives in SAE Grade 5W-30 Type Motor Oil* |
Oil | A | B | C | D | E | F | G | H | I | J |
0 | 0 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 1.25 |
1 | 200 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.92 |
2 | 0 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 1.15 |
3 | 200 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.82 |
4 | 0 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 1.15 |
5 | 200 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.82 |
6 | 0 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 1.15 |
7 | 200 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.82 |
8 | 0 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 1.15 |
9 | 200 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.00 | 0.82 |
10 | 0 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 1.15 |
11 | 200 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.00 | 0.82 |
12 | 0 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 1.15 |
13 | 200 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.00 | 0.82 |
14 | 0 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 1.15 |
15 | 200 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.00 | 0.82 |
16 | 0 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 1.15 |
17 | 200 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.00 | 0.10 | 0.82 |
*A formulated crankcase oil containing 83.2 wt % base oil, 6.2 wt % polymeric viscosity index improver, 6.9 ashless dispersant, 2.1 wt % calcium, sodium and magnesium overbased & neutral detergents, and 1.2 wt % zinc dialkyldithiophosphate. |
TABLE IIIA | ||
Oxidation Induction Time | Viscosity Increase | |
By PDSC (min) | From 72 h HOOT (%) | |
Oil # | Avg From Duplicate Runs | Avg From Duplicate Runs |
0 | 41.8 | 510.6 |
1 | 54.0 | 1650.2 |
2 | 72.9 | 89.3 |
3 | 111.2 | 59.5 |
4 | 81.8 | 68.9 |
5 | 102.8 | 48.8 |
6 | 66.8 | 129.1 |
7 | 74.3 | 102.2 |
8 | 61.3 | 150.6 |
9 | 62.6 | 417.3 |
10 | 40.8 | 728.1 |
11 | 41.8 | 1387.4 |
12 | 40.3 | 534.2 |
13 | 48.2 | 1058.8 |
14 | 34.2 | 463.2 |
15 | 46.2 | 561.7 |
16 | 39.9 | 305.0 |
17 | 39.7 | 905.8 |
TABLE IV |
Frictional Properties Of Motor Oil Blends using the High Frequency Reciprocating Rig Test |
Concentration of additives in | ||
SAE GRADE 5W-30 TYPE | ||
MOTOR OIL |
Mo- | A- | ||||
Oct | N-680 | t-Bu | P.O. | FRICTION COEFFICIENT |
Oil | ppm | wt % | wt % | wt % | 70 C | SD | 100 C | SD | 130 C | SD |
R1 | 0 | 0 | 0 | 0 | 0.117 | 0.001 | 0.116 | 0.001 | 0.116 | 0.001 |
2 | 204 | 0.125 | 0 | 0.375 | 0.117 | 0.001 | 0.113 | 0.002 | 0.113 | 0.001 |
3 | 319 | 0.125 | 0 | 0 | 0.110 | 0.001 | 0.104 | 0.004 | 0.106 | 0.004 |
4 | 432 | 0.125 | 0 | 0 | 0.105 | 0.001 | 0.095 | 0.001 | 0.091 | 0.001 |
R5 | 0 | 0.125 | 0.70 | 0.375 | 0.125 | 0.001 | 0.128 | 0.002 | 0.127 | 0.003 |
Formulated Motor Oil Components | Weight % | ||
ZDDP | 1.1 | ||
Ashless dispersant | 7.0 | ||
Viscosity Index Improver | 7.0 | ||
Neutral & Overbased Detergents | 1.4 | ||
Pour Point Depressant | 0.5 | ||
Diluent Oil | 83.0 | ||
TABLE V |
Oxidative Stability of Motor Oil Blends By the Hot Oil Oxidation Test |
Molybdenum | ||||
Amine | 2-ethyl- | % Viscosity Increase | Change | |
N-680 | hexanoate | After 74 h | % Visc | |
Sample | wt % | ppm Mo | in the HOOT | Incr |
0 | 0.15 | 0 | 70 | 0 |
1 | 0.15 | 52 | 69 | −1 |
2 | 0.15 | 104 | 68 | −2 |
3 | 0.15 | 156 | 49 | −21 |
4 | 0.15 | 208 | 43 | −27 |
5 | 0.15 | 260 | 46 | −24 |
6 | 0.15 | 312 | 35 | −35 |
7 | 0.15 | 364 | 32 | −38 |
8 | 0.15 | 416 | 27 | −43 |
9 | 0.15 | 468 | 23 | −47 |
TABLE VI |
Oxidative Stability of Motor Oil Blends By The Hot Oil Oxidation Test |
Amine | % Viscosity | Change % | ||
Sample | Wt % | PPM Mo | Increase | Viscosity |
1 | 0.125 | 0 | 55 | 0 |
2 | 0.125 | 204 | 35 | −20 |
3 | 0.125 | 318 | 27 | −28 |
4 | 0.125 | 432 | 133 | 78 |
TABLE VII |
Sequence IIIE Evaluation of |
Molybdenum/Secondary Diphenylamine Antioxidants |
Passing | ||||
Result | Limits | A | B | C |
Phenolic Content (wt %) | 0.7 | 0 | 0 | |
Amine Content (wt %) | 0.1 | 0.125 | 0.2 | |
Molybdenum Content | 0 | 458 | 115 | |
(ppm Mo) | ||||
% Vis. Inc. @ 64 h | 375 Max. | TVTM | 152 | 300 |
AE Sludge | 9.2 Min. | 9 | 9.54 | 9.56 |
APS Varnish | 8.9 Min. | 7.96 | 9.1 | 9.38 |
ORL Deposit | 3.5 Min. | 2.53 | 4.38 | 4.8 |
Stuck Ring | 2 | 2 | 1 | |
AC Wear | 30 Max. | 7.2 | 7.8 | 6.5 |
MC Wear | 64 Max. | 15.0 | 12.00 | 11.00 |
Oil Consumption in Liters | 5.1 Max. | 4.35 | 3.32 | 3.35 |
TABLE VIII |
Hot Oil Oxidation of Unadditized Base Oil |
In the Presence and Absence of Molybdenum. |
Base Oil | N-680 | Mo HEX-CEM | % Change Visc. | |
Oil # | (wt %) | (wt %) | (ppm Mo) | After 40 h |
1 | 99.75 | 0.25 | 0 | 318 |
2 | 99.65 | 0.25 | 130 | −2 |
3 | 99.55 | 0.25 | 260 | 1 |
TABLE IX | ||||||
Molyvan 855 | Process | |||||
Added | N-680 | Oil | Induction | Expected | Viscosity | |
Wt. % | Added | Added | Time | OIT | Increase | |
Oil | (ppm Mo) | Wt % | Wt % | (min) | (min) | (%) |
A | 0 | 0 | 1.25 | 26.6 | 201 | |
B | 0 | 0.1 | 1.15 | 59.4 | 42 | |
C | 0.272 (200) | 0 | 0.98 | 50.8 | 548 | |
D | 0.272 (200) | 0.1 | 0.88 | 106.2 | 83.6 | 25 |
Claims (76)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/604,285 USRE38929E1 (en) | 1995-11-20 | 2000-06-26 | Lubricant containing molybdenum compound and secondary diarylamine |
US11/133,442 USRE40595E1 (en) | 1995-11-20 | 2005-05-20 | Lubricant containing molybdenum compound and secondary diarylamine |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/559,879 US5650381A (en) | 1995-11-20 | 1995-11-20 | Lubricant containing molybdenum compound and secondary diarylamine |
US09/359,770 USRE37363E1 (en) | 1995-11-20 | 1999-07-22 | Lubricant containing molybdenum compound and secondary diarylamine |
US09/604,285 USRE38929E1 (en) | 1995-11-20 | 2000-06-26 | Lubricant containing molybdenum compound and secondary diarylamine |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/559,879 Reissue US5650381A (en) | 1995-11-20 | 1995-11-20 | Lubricant containing molybdenum compound and secondary diarylamine |
US09/359,770 Continuation USRE37363E1 (en) | 1995-11-20 | 1999-07-22 | Lubricant containing molybdenum compound and secondary diarylamine |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/559,879 Continuation US5650381A (en) | 1995-11-20 | 1995-11-20 | Lubricant containing molybdenum compound and secondary diarylamine |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE38929E1 true USRE38929E1 (en) | 2006-01-03 |
Family
ID=27000622
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/604,285 Expired - Lifetime USRE38929E1 (en) | 1995-11-20 | 2000-06-26 | Lubricant containing molybdenum compound and secondary diarylamine |
US11/133,442 Expired - Lifetime USRE40595E1 (en) | 1995-11-20 | 2005-05-20 | Lubricant containing molybdenum compound and secondary diarylamine |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/133,442 Expired - Lifetime USRE40595E1 (en) | 1995-11-20 | 2005-05-20 | Lubricant containing molybdenum compound and secondary diarylamine |
Country Status (1)
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US (2) | USRE38929E1 (en) |
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