EP0119792A2 - Hydriertes Polyisopren in einer Schmiermittelzusammensetzung - Google Patents
Hydriertes Polyisopren in einer Schmiermittelzusammensetzung Download PDFInfo
- Publication number
- EP0119792A2 EP0119792A2 EP84301570A EP84301570A EP0119792A2 EP 0119792 A2 EP0119792 A2 EP 0119792A2 EP 84301570 A EP84301570 A EP 84301570A EP 84301570 A EP84301570 A EP 84301570A EP 0119792 A2 EP0119792 A2 EP 0119792A2
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- European Patent Office
- Prior art keywords
- viscosity
- lubricants
- shear
- oils
- esters
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Definitions
- This invention relates to compositions useful as lubricating oils having high viscosity index, improved resistance to oxidative degradation and resistance to viscosity losses caused by permanent or temporary shear.
- a lubricating composition comprising (1) an hydrogenated polyisoprene having a viscosity of 1000 to 3500 centistokes at 100°C; (2) a low viscosity synthetic hydrocarbon, such as alkyl benzene or low viscosity polyalphaolefin and/or a low viscosity ester, such as monoesters, diesters, polyesters, and optionally (3) an additive package.
- a low viscosity synthetic hydrocarbon such as alkyl benzene or low viscosity polyalphaolefin and/or a low viscosity ester, such as monoesters, diesters, polyesters, and optionally (3) an additive package.
- a further object of the invention is to provide a lubricating composition with properties not obtainable with conventional polymeric thickeners.
- a further object of the invention is to provide lubricating compositions exhibiting improved shear stability, oxidative stability and excellent temperature-viscosity properties.
- the viscosity-temperature relationship of a lubricating oil is one of the critical criteria which must be considered when selecting a lubricant for a particular application.
- the mineral oils commonly used as a base for single and multigraded lubricants exhibit a relatively large change in viscosity with a change in temperature. Fluids exhibiting such a relatively large change in viscosity with temperature are said to have a low viscosity index.
- the viscosity index of a common paraffinic mineral oil is usually given a value of about 100.
- Viscosity index (VI) is determined according to ASTM Method D 2770-74 wherein the VI is related to kinematic viscosities measured at 40°C and 100°C.
- Lubricating oils composed mainly of mineral oil are said to be single graded.
- SAE grading requires that oils have a certain minimum viscosity at high temperatures and, to be multigraded, a certain maximum viscosity at low temperatures.
- an oil having a viscosity of 10 cSt. at 100°C would be an SAE 30 and if that oil had a viscosity of 3400 cP. at -20°C, the oil would be graded 10W-30.
- the viscosity requirements for qualification as multigrade engine oils are described by the SAE Engine Oil Viscosity Classification - SAE J300 SEP80, which became effective April 1, 1982.
- the low temperature (W) viscosity requirements are determined by ASTM D 2602, Method of Test for Apparent Viscosity of Motor Oils at Low Temperature Using the Cold Cranking Simulator, and the results are reported in centipoise (cP).
- the higher temperature (100°C) viscosity is measured according to ASTM D445, Method of Test for Kinematic Viscosity of Transparent and Opaque Liquids, and the results are reported in centistokes (cSt.).
- the following table outlines the high and low temperature requirements for the recognized SAE grades for engine oils.
- the 40°C viscosity estimated by linearly connecting the 100°C and -25°C viscosities would be about 70 cSt.
- V.I. improved oils have viscosities at -25°C which are considerably greater than predicted by linear extrapolation of the K.V. 100 and K.V. 40 values. Therefore, even having a V.I. of 180 does not guarantee the blend would be a 5W-40 oil.
- Polymeric VI improvers are traditionally high molecular weight rubbers whose molecular weights may vary from 10,000 to 1,000,000. Since the thickening power and VI increase are related to the molecular weight of the VI improver, most of these polymers normally have a molecular weight of at least 100,000.
- Temporary shear is the result of the non-Newtonian viscometrics associated with solutions of high molecular weight polymers. It is caused by an alignment of the polymer chains with the shear field under high shear rates with a resultant decrease in viscosity. The decreased viscosity reduces the wear protection associated with viscous oils. Newtonian fluids maintain their viscosity regardless of shear rate.
- Certain specific blends of high viscosity hydrogenated polyisoprene, low viscosity synthetic hydrocarbons and/or low viscosity esters form base fluids from which superior crankcase or gear oils can be produced by the addition of the proper additive "packages".
- the finished oils thus prepared exhibit very high stability to permanent shear and, because of their nearly Newtonian nature, very little, if any, temporary shear and so maintain the viscosity required for proper wear protection.
- the oils of this invention have remarkably better stability toward oxidative degradation than those of the prior art.
- the unexpectedly high viscosity indices produced from our base fluid blends permit the preparation of broadly multigraded crankcase fluids, such as 5W-40 and gear oils such as 75W-140. Up to now it has been difficult if not impossible, to prepare such lubricants without the use of frequently harmful amounts of polymeric V.I. improvers.
- the oligomeric polyisoprenes of this invention may be prepared by Ziegler or, preferably, anionic polymerization. Such polymerization techniques are described in United States Patent 4,060,492.
- the preferred method of preparation for the liquid hydrogenated polyisoprenes is by the anionic alkyl lithium catalyzed polymerization of isoprene.
- alkyl lithium catalysts such as secondary butyl lithium results in a polyisoprene oligomer having a very high (usually greater than 80%) 1,4-content, which results in backbone unsaturation.
- alkyl lithium catalysts are modified by the addition of ethers or amines, a controlled amount of 1,2- and 3,4- addition can take place in the polymerization.
- Structure (A) is the preferred structure because of its low Tg and because it has a lower percent of its mass in- the pendant groups (CH 3 -).
- Structure (B) is deficient in that the tetrasubsti- tuted carbons produced serve as points of thermal instability.
- Structure (C) has 60% of its mass in a pendant (isopropyl) group which, if repeated decreases the thickening power of the oligomer for a given molecular weight and also raises the Tg of the resultant polymer. This latter property has been shown to correlate with viscosity index. Optimization of structure (A) is desired for the best combination of thickening power, stability and V.I. improvement properties.
- alkyl lithium polymers Another feature of alkyl lithium polymers is the ease with which molecular weight and molecular weight distribution can be controlled.
- the molecular weight is a direct function of the monomer to catalyst ratio and, taking the proper precautions to exclude impurities, can be controlled very accurately thus assuring good quality control in the production of such polymer.
- the alkyl lithium catalysts produce very narrow molecular weight distributions such that Mw/Mn ratios of 1.1 are easily gained.
- V.I. improvers a narrow molecular weight distribution is highly desirable since, at the given molecular weight, thickening power is maximized while oxidative and shear instability are minimized.
- broad or even polymodal M.W. distributions are easily produced by a variety of techniques well known in the art.
- Star-shaped or branched polymers can also be readily prepared by the inclusion of multifunctional monomers such as divinyl benzene or by termination of the "living" chains with a polyfunctional coupling agent such as dimethylterephthal
- isoprene oligomers require hydrogenation to reduce the high level of unsaturation present after polymerization.
- 90%, and preferably 99% or more of the olefinic linkages should be saturated.
- the low viscosity synthetic hydrocarbons of the present invention having viscosities of from 1 to 10 cSt., consist primarily of oligomers of alphaolefins and alkylated benzenes.
- Low molecular weight oligomers of alphaolefins from C 8 (octene) to C 12 (dodecene) or mixtures of the olefins can be utilized.
- Low viscosity alphaolefin oligomers can be produced by Ziegler catalysis, thermal polymerization, free radically catalyzed polymerization and, preferably, BF 3 catalyzed polymerization.
- BF 3 catalyzed polymerization preferably, BF 3 catalyzed polymerization.
- a host of similar processes involving BF 3 in conjunction with a cocatalyst is known in the patent literature.
- a typical polymerization technique is described in United States Patent No. 4,045,508.
- the alkylbenzenes may be used in the present invention alone or in conjunction with low viscosity polyalphaolefins in blends with high viscosity synthetic hydrocarbons and low viscosity esters.
- the alkylbenzenes prepared by Friedel-Crafts alkylation of benzene with olefins are usually predominantly dialkylbenzenes wherein the alkyl chain may be 6 to 14 carbon atoms long.
- the alkylating olefins used in the preparation of alkylbenzenes can be straight or branched chain olefins or combinations. These materials may be prepared as shown in U.S.P. 3,909,432.
- the low viscosity esters of this invention having viscosities of from 1 to 10 cSt. can be selected from classes of esters readily available commercially, e.g., monoesters prepared from monobasic acids such as pelargonic acid and alcohols; diesters prepared from dibasic acids and alcohols or from diols and monobasic acids or mixtures of acids; and polyol esters prepared from diols, triols (especially trimethylol propane), tetraols (such as pentaerythritol), hexaols (such as dipentaerythritol) and the like reacted with monobasic acids or mixtures of acids.
- monoesters prepared from monobasic acids such as pelargonic acid and alcohols
- diesters prepared from dibasic acids and alcohols or from diols and monobasic acids or mixtures of acids
- esters examples include tridecyl pelargonate, di-2-ethylhexyl adipate, di-2-ethylhexyl azelate, trimethylolpropane triheptanoate and pentaerythritol tetraheptanoate.
- esters and mixtures of esters derived from natural sources, plant or animal are those esters and mixtures of esters derived from natural sources, plant or animal. Examples of these materials are the fluids produced from jojoba nuts, tallows, safflowers and sperm whales.
- esters used in our blends ought to be carefully selected to insure compatibility of all components in finished lubricants of this invention. If esters having a high degree of polarity (roughly indicated by oxygen content) are blended with certain combinations of high viscosity synthetic hydrocarbons and low viscosity synthetic hydrocarbons, phase separation can occur at low temperatures with a resultant increase in apparent viscosity. Such phase separation is, of course, incompatible with long term storage of lubricants under a variety of temperature conditions.
- the additive "packages" mixed with the recommended base oil blend for the production of multigraded crankcase fluids or gear oils are usually combination of various types of chemical additives so chosen to operate best under the use conditions which the particular formulated fluid may encounter.
- Additives can be classified as materials which either impart or enhance a desirable property of the base lubricant blend into which they are incorporated. While the general nature of the additives might be the same for various types or blends of the base lubricants, the specific additives chosen will depend on the particular type of service in which the lubricant is employed and the characteristics of the base lubricants.
- a finished lubricant will contain several and possibly most or all of the above types of additives in what is commonly called an "additive package.
- the development of a balanced additive package involves considerably more work than the casual use of each of the additive types. Quite often functional difficulties arising from combinations of these materials show up under actual operating conditions. On the other hand, certain unpredictable synergistic effects of a desirable nature may also become evident.
- the only methods currently available for obtaining such data are from extensive full scale testing both in the laboratory and in the field. Such testing is costly and time-consuming.
- Dispersants have been described in the literature as “detergents”. Since their function appears to be one of effecting a dispersion of particulate matter, rather than one of "cleaning up” any existing dirt and debris, it is more appropriate to categorize them as dispersants.
- Materials of this type are generally molecules having a large hydrocarbon "tail” and a polar group head.
- the tail section an oleophilic group, serves as a solubilizer in the base fluid while the polar group serves as the element which is attracted to particulate contaminants in the lubricant.
- the dispersants include metallic and ashless types.
- the metallic dispersants include sulfonates (products of the neutralization of a sulfonic acid with a metallic base), thiophosphonates (acidic components derived from the reaction between polybutene and phosphous pentasulfide) and phenates and phenol sulfide salts (the broad class of metal phenates includes the salts of alk y l p hen- ols, alkylphenol sulfides, and alkyl phenol aldehyde products).
- the ashless type dispersants may be categorized into two broad types: high molecular weight polymeric dispersants for the formulation of multigrade oils and lower molecular weight additives for use where viscosity improvement is not necessary.
- the compounds useful for this purpose are again characterized by a "polar" group attached to a relatively high molecular weight hydrocarbon chain.
- the "polar” group generally contains one or more of the elements--nitrogen, oxygen, and phosphorus.
- the solubilizing chains are generally higher in molecular weight than those employed in the metallic types; however, in some instances they may be quite similar.
- N-substituted long chain alkenyl succinimides such as products formed by the esterification of mono or polyhydric aliphatic alcohols with olefin substituted succinic acid, and Mannich bases from high molecular weight alkylated phenols.
- the high molecular weight polymeric ashless dispersants have the general formula:
- an oxidation inhibitor is the prevention of a deterioration associated with oxygen attack on the lubricant base fluid. These inhibitors function either to destroy free radicals (chain breaking) or to interact with peroxides which are involved in the oxidation mechanism.
- chain breaking e.g., 2,6-di-tert.-butyl para cresol and 4,4' methylenebis(2,6-di-tert.-butylphenol), and the zinc dithiophosphates (peroxide-destroying).
- Wear is loss of metal with subsequent change in clearance between surfaces moving relative to each other. If continued, it will result in engine or gear malfunction.
- the principal factors causing wear are metal-to-metal contact, presence of abrasive particulate matter, and attack of corrosive acids.
- Metal-to-metal contact can be prevented by the addition of film-forming compounds which protect the surface either by physical absorption or by chemical reaction.
- the zinc dithiophosphates are widely used for this purpose. These compounds were described under anti-oxidant and anti-bearing corrosion additives. Other effective additives contain phosphorus, sulfur or combinations of these elements.
- Abrasive wear can be prevented by effective removal of particulate matter by filtration while corrosive wear from acidic materials can be controlled by the use of alkaline additives such as basic phenates and sulfonates.
- conventional viscosity improvers are often used in "additive packages" their use should not be necessary for the practice of this invention since our particular blends of high and low molecular weight base lubricants produce the same effect.
- These materials are usually oil-soluble organic polymers with molecular weights ranging from approximately 10,000 to 1,000,000. The polymer molecule in solution is swollen by the lubricant. The volume of this swollen entity determines the degree to which the polymer increases its viscosity.
- pour point depressants prevent the congelation of the oil at low temperatures. This phenomenon is associated with the crystallization of waxes from the lubricants. Chemical structures of representative commercial pour point depressants are:
- Chemicals employed as rust inhibitors include sulfonates, alkenyl succinic acids, substituted imidazolines, amines, and amine phosphates.
- the anti-foam agents include the silicones and miscellaneous organic copolymers.
- Additive packages known to perform adequately for their recommended purpose are prepared and supplied by several major manufacturers. The percentage and type of additive to be used in each application is recommended by the suppliers. Typically available packages are:
- a typical additive package for an automotive gear lubricant would normally contain antioxidant, corrosion inhibitor, anti-wear agents, anti-rust agents, extreme pressure agent and foam inhibitor.
- a typical additive package for a crankcase lubricant would normally be comprised of a dispersant, antioxidant, corrosion inhibitor, anti-wear agent, anti-rust agent and foam inhibitor.
- An additive package useful for formulating a compressor fluid would typically contain an anti-oxidant, anti-wear agent, an anti-rust agent and foam inhibitor.
- This invention uses blends of HPI having a viscosity-range of 1000 to 3500 cSt. with one or more synthetic hydrocarbon fluids having viscosities in the range of 1 to 10 cSt. and/or one or more compatible ester fluids having a viscosity range of 1 to 10 cSt.
- Such blends when treated with a properly chosen additive "package", can be formulated in broad range multigraded crankcase or gear oils having improved shear stability, improved oxidative stability, and nearly Newtonian viscometric properties.
- the blends of this invention also find uses in certain applications where no additive need be employed.
- HPI low viscosity synthetic hydrocarbons
- low viscosity esters are essential parts of this invention.
- the HPI provides thickening and V.I. improvement to the base oil blend.
- the V.I. improvement produced by HPI in blends with low viscosity synthetic hydrocarbons or low viscosity esters is shown in the examples.
- the low viscosity synthetic hydrocarbon fluid is frequently the main ingredient in the base oil blend, particularly in finished lubricants having an SAE viscosity grade of 30 or 40. While certain low viscosity esters are insoluble in (high viscosity) HPI, the presence of low viscosity synthetic hydrocarbon, being a better solvent for low viscosity esters, permits greater variations in the type of esters used in base oil blends of high viscosity synthetic hydrocarbons, low viscosity synthetic hydrocarbons, and low viscosity esters.
- Crankcase and gear oils consisting solely of hydrogenated polyisoprene oligomers and low viscosity synthetic hydrocarbons with the proper additives produce synthetic fluids having excellent oxidative and hydrolytic stability.
- Such fluids are exemplified in
- the third optional component, low viscosity esters can be used in combination with hydrogenated polyisoprene oligomers - and low viscosity hydrocarbons or alone with hydrogenated polyisoprene oligomers.
- the proper choice of ester and hydrogenated polyisoprene oligomers can produce crankcase and gear oil formulations having outstanding viscosity indices and low temperature properties. Such three component blends are illustrated in Examples 1 and 2.
- Two component blends of hydrogenated polyisoprene oligomers and esters can be used to prepare multigraded lubricants having outstanding viscometric properties, detergency, and oxidative stability. While some applications present environments having high moisture levels, which would be deleterious to certain esters, there are other applications such as automotive gear oils where the high ester contents found in the hydrogenated polyisoprene oligomers- ester blends can be used to advantage.
- Example 4 illustrates the formulation of multigrade lubricants with such two component blends.
- the low viscosity hydrocarbons act as a common solvent for the HPI and the added ester. Depending on the polarity of the ester, the latter two are frequently somewhat incompatible. Excellent multigraded lubricants can be formulated with or without ester.
- the third component, low viscosity esters can be added to produce the superior lubricants of this invention.
- HPI and low viscosity synthetic hydrocarbons can be used alone to produce multigraded lubricants.
- the addition of low levels of low viscosity esters, usually 1-25% results in a base oil blend superior to blends of high viscosity synthetic hydrocarbons and low viscosity synthetic hydrocarbons alone in low temperature fluidity.
- Low viscosity esters usually constitute 10-25% of the synthetic base oil blend, more or less can be used in specific formulations. When the final application involves exposure to moisture elimination or limitation of the amount of ester in blends may be advantageous.
- the components of the finished lubricants of this invention can be admixed in any convenient manner or sequence.
- An important aspect of the present invention is in the use of the properly constituted base oil blend in combination with the proper compatible additive package to produce finished broad range multigrade lubricants having: -
- the lubricants of this invention approach viscometrics of Newtonian fluids. That is, their viscosities are changed little over a wide range of shear rates. While the HPI of the invention may, in themselves, display non-Newtonian characteristics, particularly at low temperatures, the final lubricant products utilizing low viscosity oils as diluents are nearly Newtonian.
- HPI's of this invention have molecular weights below 5000, and shear thinning of their solutions is minimal.
- the shear rates developed in pistons and gears (equal to or greater than 10 6 sec 1) is such that, depending on the polymeric thickener used, the apparent viscosity of the oils approaches that of the unthickened base fluids resulting in loss of hydrodynamic films. Since wear protection of moving parts has been correlated with oil viscosity, it is apparent that the wear characteristics of a lubricant can be downgraded as a result of temporary shear. The nearly Newtonian fluids of this invention maintain their viscosity under these use conditions and therefore afford more protection to and longer lifetime for the machinery being lubricated.
- the advantages a Newtonian fluid brings to such a grading system are obvious to anyone skilled in the art.
- the viscosity of a Newtonian fluid can be directly extrapolated to 150°C under high shear conditions.
- a polymer thickened fluid will invariably have a viscosity lower than the extrapolated value, frequently close to the base fluid itself.
- polymer thickened oils will require a more viscous base fluid.
- the use of thicker base fluids will produce higher viscosities at low temperature making it more difficult to meet the low temperature (5W for crankcase of 75W for gear oil) requirements for broadly multigraded oils.
- Viscosity index is determined by low shear viscosity measurements at 40°C and 100°C.
- the nearly Newtonian lubricants of this invention not only produce high viscosity index multigraded fluids which stay "in grade", but the VI and multigrade rating are realistic since they are not very sensitive to shear.
- the lubricants had the properties shown:
- the lubricants had the properties shown:
- the lubricants had the properties shown:
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47384183A | 1983-03-09 | 1983-03-09 | |
US473841 | 1983-03-09 | ||
US53130183A | 1983-09-09 | 1983-09-09 | |
US531301 | 1983-09-09 |
Publications (2)
Publication Number | Publication Date |
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EP0119792A2 true EP0119792A2 (de) | 1984-09-26 |
EP0119792A3 EP0119792A3 (de) | 1986-07-16 |
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ID=27044271
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Application Number | Title | Priority Date | Filing Date |
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EP84301570A Withdrawn EP0119792A3 (de) | 1983-03-09 | 1984-03-08 | Hydriertes Polyisopren in einer Schmiermittelzusammensetzung |
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EP (1) | EP0119792A3 (de) |
CA (1) | CA1225082A (de) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989009811A1 (en) * | 1988-04-08 | 1989-10-19 | The Lubrizol Corporation | Borated and non-borated overbased carboxylates as corrosion inhibitors |
US7683013B2 (en) | 2005-06-07 | 2010-03-23 | Exxonmobil Research And Engineering Company | Base stock lubricant blends for enhanced micropitting protection |
US8247358B2 (en) | 2008-10-03 | 2012-08-21 | Exxonmobil Research And Engineering Company | HVI-PAO bi-modal lubricant compositions |
US8394746B2 (en) | 2008-08-22 | 2013-03-12 | Exxonmobil Research And Engineering Company | Low sulfur and low metal additive formulations for high performance industrial oils |
US8535514B2 (en) | 2006-06-06 | 2013-09-17 | Exxonmobil Research And Engineering Company | High viscosity metallocene catalyst PAO novel base stock lubricant blends |
US8598103B2 (en) | 2010-02-01 | 2013-12-03 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low, medium and high speed engines by reducing the traction coefficient |
US8642523B2 (en) | 2010-02-01 | 2014-02-04 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
US8728999B2 (en) | 2010-02-01 | 2014-05-20 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
US8748362B2 (en) | 2010-02-01 | 2014-06-10 | Exxonmobile Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed gas engines by reducing the traction coefficient |
US8759267B2 (en) | 2010-02-01 | 2014-06-24 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
EP4353804A1 (de) * | 2022-10-11 | 2024-04-17 | Infineum International Limited | Funktionalisierte c4 bis c5 olefinpolymere und diese enthaltende schmiermittelzusammensetzungen |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3634249A (en) * | 1967-11-20 | 1972-01-11 | Exxon Research Engineering Co | Lubricating oil composition |
US4060492A (en) * | 1975-05-26 | 1977-11-29 | Sumitomo Chemical Company, Limited | Synthetic saturated oils, and their production and use |
EP0088453A1 (de) * | 1982-03-10 | 1983-09-14 | UNIROYAL CHEMICAL COMPANY, Inc. | Schmiermittelzusammensetzung |
-
1984
- 1984-03-08 CA CA000449136A patent/CA1225082A/en not_active Expired
- 1984-03-08 EP EP84301570A patent/EP0119792A3/de not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3634249A (en) * | 1967-11-20 | 1972-01-11 | Exxon Research Engineering Co | Lubricating oil composition |
US4060492A (en) * | 1975-05-26 | 1977-11-29 | Sumitomo Chemical Company, Limited | Synthetic saturated oils, and their production and use |
EP0088453A1 (de) * | 1982-03-10 | 1983-09-14 | UNIROYAL CHEMICAL COMPANY, Inc. | Schmiermittelzusammensetzung |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989009811A1 (en) * | 1988-04-08 | 1989-10-19 | The Lubrizol Corporation | Borated and non-borated overbased carboxylates as corrosion inhibitors |
US7683013B2 (en) | 2005-06-07 | 2010-03-23 | Exxonmobil Research And Engineering Company | Base stock lubricant blends for enhanced micropitting protection |
US8535514B2 (en) | 2006-06-06 | 2013-09-17 | Exxonmobil Research And Engineering Company | High viscosity metallocene catalyst PAO novel base stock lubricant blends |
US8394746B2 (en) | 2008-08-22 | 2013-03-12 | Exxonmobil Research And Engineering Company | Low sulfur and low metal additive formulations for high performance industrial oils |
US8247358B2 (en) | 2008-10-03 | 2012-08-21 | Exxonmobil Research And Engineering Company | HVI-PAO bi-modal lubricant compositions |
US8476205B2 (en) | 2008-10-03 | 2013-07-02 | Exxonmobil Research And Engineering Company | Chromium HVI-PAO bi-modal lubricant compositions |
US8598103B2 (en) | 2010-02-01 | 2013-12-03 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low, medium and high speed engines by reducing the traction coefficient |
US8642523B2 (en) | 2010-02-01 | 2014-02-04 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
US8728999B2 (en) | 2010-02-01 | 2014-05-20 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
US8748362B2 (en) | 2010-02-01 | 2014-06-10 | Exxonmobile Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed gas engines by reducing the traction coefficient |
US8759267B2 (en) | 2010-02-01 | 2014-06-24 | Exxonmobil Research And Engineering Company | Method for improving the fuel efficiency of engine oil compositions for large low and medium speed engines by reducing the traction coefficient |
EP4353804A1 (de) * | 2022-10-11 | 2024-04-17 | Infineum International Limited | Funktionalisierte c4 bis c5 olefinpolymere und diese enthaltende schmiermittelzusammensetzungen |
Also Published As
Publication number | Publication date |
---|---|
EP0119792A3 (de) | 1986-07-16 |
CA1225082A (en) | 1987-08-04 |
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