EP0391653A2 - Schmiermittelzusammensetzungen - Google Patents

Schmiermittelzusammensetzungen Download PDF

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Publication number
EP0391653A2
EP0391653A2 EP90303538A EP90303538A EP0391653A2 EP 0391653 A2 EP0391653 A2 EP 0391653A2 EP 90303538 A EP90303538 A EP 90303538A EP 90303538 A EP90303538 A EP 90303538A EP 0391653 A2 EP0391653 A2 EP 0391653A2
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EP
European Patent Office
Prior art keywords
acid
sulphur
composition according
amine
weight
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.)
Granted
Application number
EP90303538A
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English (en)
French (fr)
Other versions
EP0391653B1 (de
EP0391653A3 (en
Inventor
Arthur Samuel Thomas
Ian Macpherson
Clive Ralph Richardson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Afton Chemical Ltd
Original Assignee
Afton Chemical Ltd
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Publication of EP0391653A2 publication Critical patent/EP0391653A2/de
Publication of EP0391653A3 publication Critical patent/EP0391653A3/en
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Publication of EP0391653B1 publication Critical patent/EP0391653B1/de
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    • C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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    • C10M2229/04—Siloxanes with specific structure
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    • C10N2010/04—Groups 2 or 12
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/02—Bearings
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    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to lubricating fluid compositions, and in particular to gear oils and to additives therefor.
  • High performance gear oils usually consist of a major amount of mineral oil or synthetic base stock and a minor amount of suitable additives including in particular a sulphur-containing extreme pressure or anti-wear agent.
  • a sulphur-containing extreme pressure or anti-wear agent such as sulphur-containing materials are highly effective in promoting the extreme pressure and anti-wear properties of the oil and may also have valuable anti-oxidant properties.
  • sulphur-containing materials are detrimental to the environment, may cause undesirable odour, and can lead to corrosion of the metal parts with which they come in contact, especially parts containing copper.
  • Gear oils for example the oils used in the gear boxes and differentials of motor vehicles, and other mechanisms involving metal on metal, for example steel on steel or steel on bronze, acting parts, are required to protect the metal surfaces and particularly the teeth of the gears. Typically, such oils remain in use for long periods without being changed. In addition to providing general lubrication, the fluid protects the loaded metal parts such as the gear teeth from damage. Gear oils are customarily tested for their ability to protect gear teeth from damage such as wear and pitting for long periods. In one system for testing such oils a gear train is run under conditions of variable and very heavy stress until the gears fail.
  • lubricant compositions comprising an oil-soluble sulphurized organic compound may be improved, so as to reduce emission of volatile sulphur compounds, by inclusion of a hindered organic amine and preferably a carboxylic acid.
  • a hindered organic amine preferably a carboxylic acid.
  • the performance of gear oils can be improved by inclusion of the hindered amine with or without the carboxylic acid.
  • the compositions disclosed in this patent do not improve the performance of gear oils.
  • the present invention accordingly provides a lubricant composition
  • a lubricant composition comprising a lubricant, 1 to 20% by weight of one or more sulphur-containing extreme pressure or anti-wear agents soluble in said lubricant, from about 0.1 to about 10% of a weak acid and from about 0.05 to about 10% of an amine, or from 0.15 to 20% by weight of an amino-acid, the said percentages being based on the weight of lubricant the amount of said acid being from 0.2 to 2 equivalents per equivalent of the said amine, and the salt of said amine with the said acid being soluble in the said lubricant.
  • the proportion of the said acid is usually from 0.67 to 1.25 equivalents per equivalent of the said amine.
  • the lubricant may be a mineral oil, a synthetic oil, a natural oil such as a vegetable oil, or a mixture thereof, e.g. a mixture of a mineral oil and a synthetic oil.
  • Suitable mineral oils include those of appropriate viscosity refined from crude oil of any source including Gulf Coast, Midcontinent, Pennsylvania, California, Alaska, Middle East, North Sea and the like. Standard refinery operations may be used in processing the mineral oil.
  • Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
  • Useful synthetic hydrocarbon oils include liquid alpha olefin polymers of appropriate viscosity.
  • Hydrocarbon oils include liquid alpha olefin polymers of appropriate viscosity.
  • hydrogenated liquid oligomers of C6-C16 alpha-olefins such as hydrogentated or unhydrogenated alpha-decene trimer.
  • Alkyl-benzenes of appropriate viscosity e.g. didodecylbenzene, can also be used.
  • Useful synthetic esters include the esters of monocarboxylic and polycarboxylic acids with monohydroxy alcohols and polyols. Typical examples are didodecyl adipate, trimethylolpropane tripelargonate, pentaerythritol tetracaproate, di(2-ethylhexyl) adipate, and dilauryl sebacate.
  • Complex esters made from mixtures of mono- and di-carboxylic acids and mono- and/or polyhydric alkanols can also be used.
  • the compositions of the present invention can be blended into any such lubricant base stocks.
  • the base oil is generally a mineral oil base stock such as, for example, a conventional or solvent-refined paraffinic neutral or bright stock, a hydrotreated paraffinic neutral or bright stock, a naphthenic oil, or a cylinder oil, etc., including both straight run and blended oils.
  • synthetic base stocks such as for example poly-alpha-­olefins with synthetic diesters in weight proportions (PAO:ester) ranging from about 95:5 to about 50:50, typically about 72:25 can be used.
  • PAO:ester poly-alpha-­olefins with synthetic diesters in weight proportions
  • the base stocks used in automotive gear oils range in viscosity grades from SAE 50 to 250 and preferably from 70 to 140.
  • Suitable automotive gear oils also include cross-grades such as 75W-140, 80W-90, 85W-140, 85W-90, and the like.
  • the base stocks used in industrial gear oils have a viscosity in the range of from about ISO grade 32 to ISO grade 680 and preferably from ISO grade 68 to ISO grade 460.
  • the new lubricant compositions may be supplied either as finished lubricants ready for use or in the form of an additive package, i.e. a concentrate, which requires dilution with base lubricating fluid before use.
  • an additive package i.e. a concentrate, which requires dilution with base lubricating fluid before use.
  • the lubricant compositions of the invention may contain, in addition to the substances already mentioned, any usual additive for inclusion in such lubricants which is compatible with the sulphur-containing agent and the acid and amine. Examples of such additives are given below.
  • sulphur-containing oil-­soluble extreme pressure or anti-wear agents may be used in the compositions of the invention, and any known such agents may in principle be used.
  • the agent used contains highly active sulphur, i.e. sulphur in an amount and structural configuration such that it is capable of causing visually observable corrosive pitting of one or more gear tooth surfaces in the standard planetary spur gear test when conducted in the way described below for up to 40 hours.
  • Such agents are sulphurised olefins, sulphurised esters, sulphurised fatty acids, dialkylpolysulphides, diarylpolysulphides, dialkarylpoly­sulphides, sulphur, and sulphurized oils such as sulphurized sperm oil or sulphurized lard oil.
  • At least one of the agents used in the compositions of the present invention contains sulphur and in the preferred compositions of the invention the sulphur atoms in the sulphur containing species are highly active and generally bound directly to carbon or to more sulphur.
  • the alternative procedure is a copper coupon corrosion test which is conducted as follows: A copper coupon approximately 70 X 15 mm and about 1.25 mm in thickness is cleaned with steel wool (0000 grade), washed with heptane, and then with acetone, dried, and weighed to the nearest 0.1 mg. The cleaned coupon is placed in a test tube and covered completely with the composition to be tested, and the system is heated to 125°C in an oil bath maintained at this temperature.
  • the copper coupon is removed from the test tube, rinsed with heptane and then with acetone.
  • the dried coupon is then rubbed with a paper towel moistened with acetone to remove any surface flakes formed by copper corrosion.
  • the coupon is then air-dried and weighed to the nearest 0.1 mg.
  • the difference in weight between the initial copper coupon and the coupon after the test represents the extent to which the copper has been corroded under the test conditions: the larger the weight difference, the greater the copper corrosion, and thus the more active the sulphur compound.
  • a sulphur-containing extreme pressure or anti-wear agent is regarded as "highly-active" if the coupon weight loss in the above test is above 50 milligrams. If the weight loss is from 30 to 50 milligrams, the agent should be subjected to the planetary spur gear test in order to determine whether it is "highly active" or not.
  • sulphur-containing compounds which possess a linkage of two sulphur atoms (i.e., -S-S-) or four or more sulphur atoms (e.g., -S-S-S-S-, -S-S-S-S-S-, etc.) tend to be "highly active” in the sense used herein.
  • a product from one manufacturer for example sulphurised isobutene, may be "highly active” whereas a similar product from another manufacturer may not be “highly active”.
  • One preferred class of such agents is made by reacting an olefin such as isobutene with sulphur.
  • the product e.g. sulphurized isobutene
  • a wide variety of other olefins or saturated hydrocarbons may be used in place of the isobutene.
  • sulphur-containing extreme pressure agents which may be used in the compositions of the invention are sulphur and the sulphur- and phosphorus-containing additives already mentioned, especially the thiophosphates and dithiophosphates, e.g. zinc dialkyl or diaryl dithiophosphates or trihydrocarbyldithiophosphates, customarily included in lubricant compositions as extreme pressure or anti-wear agents.
  • compositions of the present invention may contain, as an extreme pressure or anti-wear agent, an ester of a pentavalent acid of phosphorus, such as a fully or partially esterified phosphoric, phosphonic or pyrophosphoric acids or a sulphur-containing analog thereof.
  • an ester of a pentavalent acid of phosphorus such as a fully or partially esterified phosphoric, phosphonic or pyrophosphoric acids or a sulphur-containing analog thereof.
  • Such compounds have the formula: wherein each of R1, R2 and R3 is, independently, hydrogen or a hydrocarbyl group, provided that at least one of R1, R2 and R3 is hydrocarbyl, and each X is oxygen or sulphur, at least one X preferably being sulphur.
  • R1 groups are hydrocarbyl groups, the balance, if any, being hydrogen atoms, and R2 and R3, when hydrocarbyl, can be aromatic, cycloaliphatic, and/or aliphatic hydrocarbon groups, or any combination of these.
  • R1, R2 and R3 are saturated or substantially saturated aliphatic, cycloaliphatic or polycycloaliphatic groups, such as alkyl, alkenyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkenylalkyl, cycloalkenylalkenyl, and the like.
  • hydrocarbyl groups are such that the compound is soluble in the base oil to at least the desired use concentration at ambient temperatures.
  • the hydrocarbyl groups can contain functional substituents or non-hydrocarbon component groups which do not materially alter the predominantly hydrocarbon character of the hydrocarbyl groups themselves.
  • the proportion of sulphur-containing extreme pressure or antiwear agent included in the compositions of the invention is preferably such that the molar ratio of the sulphur in the said sulphur-containing extreme pressure or anti-wear agent to the amino nitrogen in the amine or amino acid is from 40:1 to 5:1, and is typically 1.7 to 10% by weight, usually 2-4%, based on the weight of the lubricant.
  • the total sulphur content of the extreme pressure or antiwear agent should be taken into account, even though some of the sulphur in the agent may not qualify as "highly active" in the strict sense explained above.
  • the new compositions preferably contain a phosphorus-containing extreme pressure or antiwear agent.
  • the sulphur-containing agent may itself contain phosphorus, or a separate phosphorus-­containing agent may be used with the sulphur-containing agent (which may itself contain phosphorus).
  • Such separate phosphorus-containing agents include derivatives of phosphorus oxyacids and of polyphosphorus oxyacids such as phosphites, phosphates and pyrophosphates, and especially their oil-soluble esters, acid esters and amine salts.
  • hydrocarbyl groups may be alkyl, alkenyl, phenyl, alkylphenyl or dialkylphenyl.
  • esters are monomethyl, dimethyl, mono-n-butyl, di-n-butyl, mono-isobutyl, di-isobutyl, monoamyl, diamyl, di-n-octyl, di-(2-ethyl-n-hexyl), monooleyl, dioleyl, monophenyl, diphenyl and di(dodecylphenyl) phosphite and phosphate, and their amine salts.
  • Such phosphorus-containing agents are usually included in the new compositions in a proportion of 0.01 to 3.5% based on the weight of the lubricant.
  • the compositions of the invention may also contain an alkali metal borate, e.g. sodium or potassium borate, e.g. in a proportion of 0.5 to 8% by weight of the lubricant.
  • the acid used in the new compositions is a weak acid, preferably one having a pKa of greater than about 2.0, and is usually a carboxylic acid in which one or more carboxyl groups are attached to a hydrocarbon radical of 1 to 100, preferably 2 to 36 carbon atoms.
  • Other weak acids e.g. a boric acid such as H3BO3 or metaboric acid, may also be used, e.g. in a amount from 0.1 to 8.0% by weight of the lubricant.
  • suitable acids are alkanoic and alkenoic mono-, di- or poly-carboxylic acids of 1 to 100, preferably 2 to 54, carbon atoms, e.g.
  • acetic acid n-octanoic acid, decanoic acid, myristic acid, oleic acid, linoleic acid, tetrapropenylsuccinic acid, azelaic acid, or dimerised or trimerised linoleic acid.
  • the acid used must be such as to form an oil-soluble salt with the amine used.
  • Acyclic monocarboxylic acids are preferred.
  • amines are aliphatic mono and polyamines containing 2 to 22 carbon atoms per molecule.
  • Primary, secondary and tertiary amines are all suitable.
  • Especially preferred amines are linear or branched aliphatic, cycloaliphatic or ethylenically unsaturated aliphatic amines of 6 to 22 carbon atoms, e.g. n-octylamine, oleylamine, or cyclohexylamine, polyethylene polyamines such as triethylene tetramine, and the tertiary alkyl primary amines sold under the trade names Primene 81-R and Primene JM-T.
  • the amine must be capable of forming an oil-soluble salt with the acid used.
  • the combined proportions of the carboxylic acid and of the amine used may be from 0.15 to 20.0% by weight of the lubricant, preferably 0.15 to 2.0%, and especially about 0.3%, but their respective amounts depend as already indicated on their molecular weights and the mole equivalence of the particular acid and amine used.
  • the total amount of acid plus amine is typically 5 to 300%, preferably 20 to 100%, by weight.
  • an amino-acid may be used in the same total amount as a percentage based on the weight of the lubricant.
  • Suitable amino-acids include glycine, alanine, and phenylalanine.
  • compositions of the invention consist essentially of a solution of various organic compounds normally in an oil which is usually a hydrocarbon oil, the compositions have, in a strict sense, no pH. However, it has been found that if a sample of the composition is diluted in a mixture of methanol and toluene and then assayed with a conventional pH probe as used in aqueous systems, a measurement is obtained which provides a useful measure of the relative proportions of basic and acidic materials present in the composition. Measured in this way, the pH of the compositions of the invention should be in the range of 3 to 10 or preferably of 7 to 9.
  • compositions of the invention may contain other additives suitable for use in gear oils, for example: Antioxidants Zinc dialkyldithiophosphates, zinc diaryldithiophosphates, hindered phenols, amines and various organic compounds containing nitrogen, sulphur or phosphorus. Antifoamants and demulsification agents Silicone based fluids, ethylene glycol-propylene glycol condensation products, polyalkylacrylates. Dispersants Polyalkenyl succinimides, succinate esters, N-vinyl-­pyrrolidone-methacrylate ester copolymers, fatty acid esters and fatty acid amides, and carboxylic acid derivative compositions (e.g.
  • succinimides succinic acid esters, succinic acid ester-amides, etc.
  • one or more post-treating reagents such as boron oxide, boron oxide hydrate, boron halides, boron acids, esters of boron acids, carbon disulphide, hydrogen sulphide, sulphur, sulphur chloride, alkenyl cyanides, carboxylic acid acylating agents (e.g.
  • maleic anhydride maleic acid, fumaric acid, malic acid, azelaic acid, adipic acid, C1 to C30 alkenyl succinic acids, C1 to C30 alkenylsuccinic anhydrides, etc.
  • aldehydes ketones, urea, thiourea, guanidine, dicyandiamide, hydrocarbyl phosphates, hydrocarbyl phosphites, hydrocarbyl thiophosphates, hydrocarbyl thiophosphites, phosphorus sulphides, phosphorus oxides, phosphoric acid, phosphorous acid, hydrocarbyl thiocyanates, hydrocarbyl isocyanates, hydrocarbyl isocyanates, hydrocarbyl isothiocyanates, epoxides, episulphides, formaldehyde or formaldehyde producing compounds plus phenols, and sulphur plus phenols.
  • Detergents Metal salts of organic salicylates, sulphonates, phenates or phosphonates. Viscosity index improvers or pour point depressants Polyalkylmethacrylates or olefin copolymers. Friction Modifiers Alkyl or alkenyl fatty acid amides, alkyl or alkenyl succinimides, or alkyl or alkenyl phosphonates.
  • the invention includes within its scope lubricant additive concentrates comprising 5 to 95% of one or more sulphur-containing extreme pressure or anti-wear agents, from 0.5 to 20% of a weak acid and from 1 to 20% of an amine, or from 0.5 to 25% of an amino acid, and a diluent oil, the said percentages being by weight based on the total weight of the concentrate, the amount of said acid being from 0.2 to 2 equivalents per equivalent of the said amine.
  • Such concentrates may also contain 1 to 50% of one or more phosphorus-containing extreme pressure or anti-wear agents.
  • compositions of the invention can conveniently be made by modification of existing compositions by adding appropriate amounts of acid and amine thereto.
  • Example 1 Example 2
  • Example 3 Sulphurised Isobutylene HiTEC 312 (45 ⁇ 3%S) 3.9 3.9 - - - - HiTEC 309 (45 ⁇ 3%S) - - 3.9 3.9 - - Anglamol 33 (45 ⁇ 3%S) - - - - - 3.9 3.9 2-Ethylhexyl-acid phosphate/oleylamine salt 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36
  • Copper Deactivator 0.07 0.07 0.07 0.07 0.07 0.07 0.07 Antifoam 0.06 0.06 0.06 0.06 0.06 0.06 0.06 0.06 0.06 0.06 0.06 Octanoic Acid 0.5 0.5 0.5 0.5 0.5 0.5 0.5 n-Octylamine - 0.6 - 0.6 - 0.6
  • blends contain 12.1 moles of sulphur per mole of amino nitrogen in the n-octylamine salt and 0.77 equivalents of octanoic acid per equivalent of n-octylamine.
  • a lubricating fluid of SAE 90 grade viscosity characteristics was blended with sulphurised isobutylene (2.2% w/w), an alkylamine/alkylphosphate/alkylphosphite/­alkylthiophosphate mixture (0.5% w/w), and octanoic acid in a proportion such that there were approximately 135.6 moles of sulphur per mole of said acid.
  • the sulphurised isobutylene itself contained 45% sulphur (w/w).
  • the alkylamine is entirely neutralised by the phosphorus acids present.
  • a sample of the fluid described above was then treated with an n-octylamine/n-octanoic acid mixture (in equivalent amounts; 0.3% w/w) and then subjected to the same planetary spur gear test.
  • the fluid contained about 38.2 moles of sulphur per mole of amino nitrogen, apart from the nitrogen sulphurised by the phosphorus acids, and 0.9 equivalents of octanoic acid per equivalent of amino nitrogen. This gave a performance of over 75 hours before excessive gear damage was observed.
  • Lubricating fluids produced in accordance with the present invention are capable of enabling at least 60 and in preferred embodiments over 75 hours of running time in the test.
  • a sample of the first lubricating fluid described in Example 4 was treated with an acetic acid/oleylamine mixture (0.11% w/w acetic acid; 0.54% w/w oleylamine), and then subjected to the planetary spur gear test.
  • the fluid contained approximately 23 moles of sulphur per mole of amino nitrogen, other than that salified by the phosphorus acids, and 0.95 equivalents of acetic acid per equivalent of amino nitrogen. Satisfactory performance of over 60 hours was obtained.
  • Example 4 A sample of the first lubricating fluid described in Example 4 was treated with a mixture of tetrapropenyl­succinic acid and triethylenetetramine (0.22% w/w acid and 0.04% w/w amine), and then subjected to the planetary spur gear test.
  • the fluid contained approximately 29.4 moles of sulphur per mole of amino nitrogen other than that salified by the phosphorus acids. Satisfactory performance over 60 hours was obtained.

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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)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)
EP90303538A 1989-04-03 1990-04-02 Schmiermittelzusammensetzungen Expired - Lifetime EP0391653B1 (de)

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GB8907474 1989-04-03
GB898907474A GB8907474D0 (en) 1989-04-03 1989-04-03 Lubricant compositions

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519760A1 (de) * 1991-06-21 1992-12-23 Ethyl Petroleum Additives, Inc. Öl-Zusatz-Konzentrate und Schmiermittel mit verbesserten Leistungsmöglichkeiten
EP0531585A1 (de) * 1991-09-09 1993-03-17 Ethyl Petroleum Additives Limited Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen
GB2288815A (en) * 1994-04-08 1995-11-01 Exxon Chemical Patents Inc Lubricating oil anti-wear additives
GB2301113A (en) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Ltd Extreme pressure gear lubricant
WO1997014770A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids of improved antiwear performance
US6103675A (en) * 1997-03-12 2000-08-15 Clariant Gmbh Phosphoric esters as extreme pressure additives
SG89329A1 (en) * 1999-06-01 2002-06-18 Oronite Japan Ltd Gear lubricating oil composition
EP1233051A1 (de) * 2001-02-20 2002-08-21 Ethyl Corporation Saubere niedrigphosphorhaltige Getriebeöl-Formulationen
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
US7759294B2 (en) * 2003-10-24 2010-07-20 Afton Chemical Corporation Lubricant compositions
US7803332B2 (en) 2005-05-31 2010-09-28 Exxonmobil Chemical Patents Inc. Reactor temperature control
AT519436A1 (de) * 2016-11-15 2018-06-15 Ac2T Res Gmbh Chalkogenhaltige Aminosäuren als Reagens zur In-situ-Erzeugung tribotechnisch vorteilhafter Oberflächen(schichten) von Gleitpartnern
CN111032837A (zh) * 2017-10-02 2020-04-17 出光兴产株式会社 汽车用齿轮油组合物、和润滑方法

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JPH06200274A (ja) * 1992-12-29 1994-07-19 Tonen Corp 終減速機用潤滑油組成物
US7452851B2 (en) 2003-10-24 2008-11-18 Afton Chemical Corporation Lubricant compositions
US8034754B2 (en) 2005-03-31 2011-10-11 The Lubrizol Corporation Fluids for enhanced gear protection
US20080302487A1 (en) 2007-06-07 2008-12-11 Closure Medical Corporation Mesh dispenser
RU2658917C2 (ru) * 2014-02-03 2018-06-26 Фукс Петролюб Се Композиции присадок и промышленные технические жидкости

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US3013970A (en) * 1955-01-27 1961-12-19 Lubrizol Corp Gear lubricant improving agents
US3389083A (en) * 1967-01-26 1968-06-18 Chevron Res Lubricants containing alkali metal dithiophosphates
US3398095A (en) * 1967-11-13 1968-08-20 Shell Oil Co Vapor-space inhibitors
US4263155A (en) * 1980-01-07 1981-04-21 Chevron Research Company Lubricant composition containing alkali metal borate and stabilizing oil-soluble acid
GB2115000B (en) * 1982-02-17 1985-02-06 Shell Int Research Lubricating oils and hydraulic fluids
CA1208208A (en) * 1982-05-07 1986-07-22 Kirk E. Davis Sulfurized olefin-containing compositions
US4615818A (en) * 1985-03-15 1986-10-07 The Lubrizol Corporation Hydrogen sulfide stabilized oil-soluble sulfurized organic compositions
US4690767A (en) * 1985-03-15 1987-09-01 The Lubrizol Corporation Hydrogen sulfide stabilized oil-soluble sulfurized organic compositions

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0519760A1 (de) * 1991-06-21 1992-12-23 Ethyl Petroleum Additives, Inc. Öl-Zusatz-Konzentrate und Schmiermittel mit verbesserten Leistungsmöglichkeiten
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
EP0531585A1 (de) * 1991-09-09 1993-03-17 Ethyl Petroleum Additives Limited Öladditivkonzentrate und Schmieröle mit verbesserten Leistungen
GB2288815A (en) * 1994-04-08 1995-11-01 Exxon Chemical Patents Inc Lubricating oil anti-wear additives
GB2301113A (en) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Ltd Extreme pressure gear lubricant
WO1997014770A1 (en) * 1995-10-18 1997-04-24 Exxon Chemical Patents Inc. Power transmitting fluids of improved antiwear performance
US6103675A (en) * 1997-03-12 2000-08-15 Clariant Gmbh Phosphoric esters as extreme pressure additives
SG89329A1 (en) * 1999-06-01 2002-06-18 Oronite Japan Ltd Gear lubricating oil composition
EP1233051A1 (de) * 2001-02-20 2002-08-21 Ethyl Corporation Saubere niedrigphosphorhaltige Getriebeöl-Formulationen
US6844300B2 (en) 2001-02-20 2005-01-18 Ethyl Corporation Low phosphorus clean gear formulations
US7759294B2 (en) * 2003-10-24 2010-07-20 Afton Chemical Corporation Lubricant compositions
US7648948B2 (en) 2005-04-08 2010-01-19 Exxonmobil Chemical Patents Inc. Additive system for lubricants
US7902132B2 (en) 2005-04-08 2011-03-08 The Lubrizol Corporation Additive system for lubricants
US7803332B2 (en) 2005-05-31 2010-09-28 Exxonmobil Chemical Patents Inc. Reactor temperature control
AT519436A1 (de) * 2016-11-15 2018-06-15 Ac2T Res Gmbh Chalkogenhaltige Aminosäuren als Reagens zur In-situ-Erzeugung tribotechnisch vorteilhafter Oberflächen(schichten) von Gleitpartnern
AT519436B1 (de) * 2016-11-15 2021-10-15 Ac2T Res Gmbh Chalkogenhaltige Aminosäuren als Reagens zur In-situ-Erzeugung tribotechnisch vorteilhafter Oberflächen(schichten) von Gleitpartnern
CN111032837A (zh) * 2017-10-02 2020-04-17 出光兴产株式会社 汽车用齿轮油组合物、和润滑方法
US11421175B2 (en) * 2017-10-02 2022-08-23 Idemitsu Kosan Co., Ltd. Gear oil composition for automobile, and lubrication method

Also Published As

Publication number Publication date
CA2013565A1 (en) 1990-10-03
JPH02298590A (ja) 1990-12-10
EP0391653B1 (de) 1994-03-02
DE69006883D1 (de) 1994-04-07
EP0391653A3 (en) 1990-12-27
DE69006883T2 (de) 1994-06-09
GB8907474D0 (en) 1989-05-17
JP2912414B2 (ja) 1999-06-28
AU630177B2 (en) 1992-10-22
AU5251290A (en) 1990-10-04
ES2062346T3 (es) 1994-12-16

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