EP0434464A1 - Übergangsmetallfreies Schmiermittel - Google Patents

Übergangsmetallfreies Schmiermittel Download PDF

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Publication number
EP0434464A1
EP0434464A1 EP90314188A EP90314188A EP0434464A1 EP 0434464 A1 EP0434464 A1 EP 0434464A1 EP 90314188 A EP90314188 A EP 90314188A EP 90314188 A EP90314188 A EP 90314188A EP 0434464 A1 EP0434464 A1 EP 0434464A1
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EP
European Patent Office
Prior art keywords
lubricant composition
carbon atoms
composition according
wear
alkyl
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
EP90314188A
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English (en)
French (fr)
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EP0434464B1 (de
Inventor
David Kenvyn Walters
Arthur Samuel Thomas
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
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Afton Chemical Ltd
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    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/10—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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    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
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    • C10M135/20—Thiols; Sulfides; Polysulfides
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    • C10M159/12—Reaction products
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
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    • C10M159/12—Reaction products
    • C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
    • C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/38—Conveyors or chain belts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/40—Generators or electric motors in oil or gas winning field
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/42—Flashing oils or marking oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/44—Super vacuum or supercritical use
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/50—Medical uses
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • This invention relates to lubricant compositions, and more especially to lubricant compositions which can be used as hydraulic fluids.
  • Lubricant compositions normally contain a variety of additives incorporated to improve the performance of the lubricant in the environment in which it is to be used. Such additives often contain transition metals. As is well known, there is now a general need, for environmental reasons, to reduce the use of transition metals which are frequently toxic. For example, lubricants used as hydraulic fluids often contain, as an anti-wear additive, a zinc dialkyl dithiophosphate (a so-called "ZDDP"). It is desirable to be able to provide hydraulic fluids which are zinc free. This is especially true where the hydraulic fluid is to be used in agriculture or arboriculture where spillage of the fluid onto cultivated land may occur and cause pollution of the land and of any drainage or river system connected with it.
  • ZDDP zinc dialkyl dithiophosphate
  • a universal anti-wear (UAW) additive system for use in such hydraulic fluids must be capable of providing fluids capable of meeting the specifications of the leading hydraulic pump manufacturers, e.g. the Haglunds-Denison HFO specification and the Vickers Vane pump specification. It is a further requirement for such fluids that they must meet higher than load stage 10 performance in the FZG test described in more detail below.
  • Hydraulic fluids incorporating ZDDPs do not always give the required performance in the FZG test.
  • a lubricant composition comprises (a) a metal-free anti-wear or load carrying additive containing sulphur and/or phosphorus, and (b) a corrosion inhibitor in the form of an amino succinate ester of formula in which R1 and R2 are each alkyl of 1 to 30, preferably 1 to 12, carbon atoms, R3, R4 and R5 are each hydrogen or alkyl of 1 to 4 carbon atoms, and R6 and R7 are each hydrogen, alkyl of 1 to 30 carbon atoms, or an acyl group derived from a saturated or unsaturated carboxylic acid of up to 30 carbon atoms, at least one of R 6 and R7 being a said acyl group.
  • R1 and R2 are each alkyl of 1 to 30, preferably 1 to 12, carbon atoms
  • R3, R4 and R5 are each hydrogen or alkyl of 1 to 4 carbon atoms
  • R6 and R7 are each hydrogen, alkyl of 1 to 30 carbon atoms, or an acyl group derived
  • R1 and R2 are each alkyl of 3 to 6 carbon atoms, e.g. isobutyl, R3, R4 and R5 are each hydrogen, and R6 and R7 are each alkyl of 15 to 20 carbon atoms or an acyl radical derived from a saturated or unsaturated dicarboxylic acid containing 4 to 10 carbon atoms, e.g. octadecyl, octadecenyl, or 3-carboxy-1-oxo-2propenyl.
  • An especially preferred component (b) is aspartic acid, N-(3-carboxy-1-oxo-2-propenyl)-N-octadecyl-bis(2-methylpropyl)ester.
  • the metal free, and preferably ashless, anti-wear or load carrying additive may be any one of a wide range of sulphur- and/or phosphorus-containing additives, for example a mono- and/or di-hydrocarbyl phosphate or phosphite wherein the hydrocarbyl radical is alkyl of up to 12 carbon atoms, e.g. n-butyl, iso-butyl, n-amyl, n-octyl, 2-ethylhexyl or n-dodecyl, or a mixture thereof, and amine salts of such phosphates and phosphites, for example with primary amines of 4 to 18 carbon atoms, e.g.
  • n-butylamine, n-octylamine, tert-octyl primary amine, n-dodecylamine the commercially available mixture of tertiary alkyl primary amines such as Primene 81R in which the tertiary alkyl radicals contain 12 to 14 carbon atoms each, n-octadecylamine, oleylamine, and also secondary and tertiary amines such as di-n-octylamine, and tri-n-octylamine.
  • compositions of the present invention are sulphurized hydrocarbyl phosphites such as mono- and di-hydrocarbyl thiophosphates wherein the hydrocarbyl radical may be aryl, e.g. phenyl, alkylaryl, e.g. alkylphenyl in which the alkyl contains up to 12 carbon atoms, arylalkyl, or aliphatic, e.g. alkyl of up to 12 carbon atoms.
  • Examples of such sulphurized hydrocarbyl phosphites includes diphenylthiophosphate, dinonylphenyl thiophosphates, di-n-butyl thiophosphate, di-isobutyl thiophosphate and di-2-ethylhexyl thiophosphate. Amine salts of such thiophosphates may also be used.
  • the anti-wear or load-carrying additive may also be a tri-hydrocarbyl di-thiophosphate in which each hydrocarbyl group may be, for example, an aromatic, alkylaromatic, cycloaliphatic, or aliphatic radical as aforesaid, e.g. isopropyl, n-butyl, isobutyl, n-pentyl, n-hexyl, 2-ethylhexyl or n-dodecyl.
  • the hydrocarbyl group may also be an alkenyl or cycloalkyl radical.
  • metal free antiwear or load carrying additives which can be used in the invention are sulphurized alkenes, e.g. sulphurized isobutene, containing, for example 42 to 48% by weight of sulphur or a sulphurized carboxylic acid or ester thereof in which the acid is, for example a fatty acid such as oleic or linoleic acid, e.g. a sulphurized vegetable oil or animal fat such as rape seed oil or lard oil.
  • sulphurized alkenes e.g. sulphurized isobutene
  • Suitable commercially available sulphurised fatty ester materials of this type include Sulperm 10S (Keil Chemical) and EP oil GE10 (Hornett). These typically contain about 9.5% and about 8.5-9.5% sulphur, respectively.
  • Dialkylpolysulphides such as t-nonyl trisulphide or t-dodecyl pentasulphide can also be used as the anti-wear or load-carrying additive.
  • anti-wear or load carrying additive is advantageously prepared in the way described in our British Patent Application No. 8829597.7 (continued under Application No. 8928565.4 and published as GB-A-2226028).
  • These anti-wear or load-carrying additives are amine salts of phosphorothioic acids of formula: in which the radicals R are the same or different and each is a substituted or unsubstituted hydrocarbyl radical of up to 20 carbon atoms and R1, R2 and R3 are each hydrogen or substituted or unsubstituted hydrocarbyl radicals of up to 22 carbon atoms, not more than 2 of R1, R2 and R3 being hydrogen.
  • such salts When produced by the process of the aforesaid application, such salts have a purity of at least 95% and have little reactivity towards copper, and less than 3% of a phosphite of formula (RO)2POH in which R is as hereinbefore defined or amine salt thereof.
  • Preferred such amine salts are those in which R is alkyl of 3 to 8 carbon atoms or phenyl and each of R1, R2 and R3 is hydrogen or an alkyl, cycloalkyl or alkenyl radical of 4 to 22 carbon atoms, not more than 2 of R1, R2 and R3 being hydrogen.
  • R is phenyl
  • R1 and R2 are hydrogen
  • R3 is mixed C12-C14 tertiary alkyl.
  • Such amine salts are made by forming a mixture of sulphur and the amine in the liquid state, adding to the mixture a phosphite ester of formula (RO)2POH in an amount at least equivalent to the amount of sulphur under conditions such that the sulphur reacts with the ester but the reaction temperature does not rise above 130°C, and then continuing the reaction until the solid sulphur has substantially disappeared from the reaction mixture.
  • the quantity of amine is adjusted if necessary so that the total quantity of amine is at least equivalent to the quantity of the phosphite ester.
  • the proportions of components (a) and (b) in the lubricant compositions of the invention are preferably from 0.05 to 3%, preferably 0,1% to 1.5%, of the antiwear or load carrying additive and from 0.002% to 0.5%, preferably 0.05 to 0.25%, by weight of the corrosion inhibitor, such percentages being by weight based on the total weight of the lubricant composition.
  • the lubricant composition may include as the base fluid any mineral or non-mineral oil suitable for use as a lubricant, or more especially as a hydraulic fluid.
  • base stocks include paraffinic lubricating oil base stocks of mineral origin, synthetic oils such as polyalphaolefins, e.g. hydrogenated polydecene, synthetic lubricant esters, such as dialkyl adipates and azelates (in which the alkyl groups typically have 1 to 20 carbon atoms each, e.g.
  • oils of biological origin including more particularly lubricant vegetable oils such as rape seed oil, jojoba oil, cotton seed oil, peanut oil or palm oil.
  • the combination of components (a) and (b) as set out above is compatible with a variety of oils of natural, especially vegetable, origin suitable for use as hydraulic fluids.
  • oils of natural are biodegradable, and in consequence the present invention makes it possible to provide an effective hydraulic fluid based on a biodegradable base stock such as rape seed oil or jojoba oil and incorporating additives which are free from heavy metals.
  • a third component viz. (c) an alkaline earth metal alkylbenzene sulphonate, alkylnaphthalene sulphonate, petroleum sulphonate, alkylphenate, alkyl sulphurized phenate, or alkylsalicylate.
  • This material is usually overbased and may also be sulphurized.
  • a sulphurized overbased calcium alkylphenate in which the alkyl group is paranonyl, or a calcium dinonylnaphthalene-sulphonate is preferably used.
  • the proportion of such additional additive is usually in the range 0.005 to 0.50% based on the total weight of the composition.
  • Such compositions are not ashless, but they do not contain heavy metals and thus achieve one of the major objectives of the present invention.
  • lubricant compositions of the present invention may incorporate other additives conventionally used in lubricants, for example:
  • compositions of the invention are conveniently supplied to the formulator of the finished lubricant composition in the form of an additive concentrate comprising the components (a) and (b) as aforesaid, alone or preferably with a relatively small amount of suitable base oil to facilitate handling, and optionally with one or more of the additional ingredients mentioned above.
  • the amounts of components (a) and (b) are proportioned such that when the concentrate is blended into a base fluid to provide a finished lubricant composition in which the concentration of component (a) is from 0.05 to 3% by weight and preferably from 0.1 to 1.5% by weight based on the total weight of the lubricant composition, the concentration of component (b) is from 0.002 to 0.5% by weight and preferably from 0.05 to 0.25 by weight based on the total weight of the lubricant composition.
  • the ratio of (a) to (b) in such concentrates is preferably 30: 1 to 0.4: 1.
  • the proportion of component (b) in the concentrate is preferably from 0.1 to 50% by weight, especially 0.1 to 10%, and most commonly 1 to 5% by weight of the concentrate.
  • Hydraulic fluid blends were prepared using as the base stock an ISO 46 mineral base oil having a kinematic viscosity range at 40°C of from 41.4 to 50.6 cSt.
  • the additives incorporated were as stated below Tables I and II which follow.
  • Each blend was evaluated for clarity and by the IP 135B corrosion test. The latter test involved stirring a mixture of 300 ml of the hydraulic fluid with 30 ml of artificial sea water at a temperature of 60°C with a steel cylinder immersed in the mixture. The test was run in duplicate for 24 hours with each blend and the immersed steel specimens were then examined for signs of rusting. For a pass, no rust must be visible on the specimen.
  • the blends were also examined by the FZG test (IP334/79).
  • FZG test IP334/79
  • two steel spur gears were rotated together with oil dip lubrication for a series of 15 minute stages.
  • the relative torque between the gears was increased by a fixed amount after each stage and the gears were run together for a given period after which they were examined for wear or damage.
  • the result of the test is quoted in terms of the final pass stage and the first fail stage. To be satisfactory, the pass stage must be higher than 10.
  • Blend 4 5, 6, 7 and 10 are in accordance with the present invention.
  • the other blends are for comparison.
  • Component A1 was the Primene 81R salt of diphenylthiophosphate.
  • Component A2 was a blend of 36% di-t-nonyl polysulphide and 64% sulphurised fatty ester
  • Component B was aspartic acid, N-(3 carboxy-2-oxo-2-propenyl)N-octadecyl-bis(2-methylpropyl)ester.
  • Corrosion Inhibitor D was a condensation product of dodecenyl succinic acid and oleic acid with a polyethylene polyamine
  • Corrosion Inhibitor E was octylamine octanoate.
  • Corrosion Inhibitor F was a modified imidazoline (Monamulse CI)
  • Blends 1-6 contained the same levels of conventional antioxidant, copper deactivator and demulse aid.
  • Blends 2 and 5 additionally contained a boronated polyisobutenyl succinimide ashless dispersant in conventional amount.
  • component A1 was prepared in the way described in GB-A-2226028.
  • Components A1, A2, B, D and F were as in Table I.
  • Detergent C1 was an overbased calcium sulphurised nonylphenate.
  • Detergent C2 was calcium dinonyl naphthalene sulphonate
  • Corrosion Inhibitor G was butanedioic acid, sulpho-1,4-tridecyl ester, sodium salt.
  • Blends 7, 8 and 9 contained the same levels of conventional antioxidant, copper deactivator, VI improver and demulse aid.
  • Blend 10 similar to blends 7 to 9 but contained a boronated polybutenyl succinimide ashless dispersant in conventional amount and no VI improver.
  • a blend 11 was prepared having the same composition as blend 6 described in Example 1 except that the base oil was rape seed oil.
  • the results in the FZG test, the IP135B test, and the clarity of the blend were the same as those obtained with blend 6.
  • a blend 12 was prepared having the same composition as blend 6 described in Example 1 except that component A1 was used at a concentration of 0.11 weight percent, and component A2 was composed entirely of the sulphurised fatty ester (Sulperm 10S). Blend 12 produced the same FZG, IP135B, and clarity results as blend 6. In performance testing, blend 12 met the requirements of the Haglunds-Denison HFO specification, the Cincinnati Milacron P68, P69 and P70 specifications, and the Vickers vane pump specification.
  • a blend 13 was prepared by blending the additive components of blend 12 described in Example 3 in the same concentrations as blend 12 with rape seed oil. Blend 13 gave the same FZG, IP135B, and clarity results as blend 11 described in Example 2. In further testing blend 13 was found to satisfy the pump test requirements of the Haglunds-Denison HFO specification, as well as the Cincinnati Milacron thermal stability test procedure "A". In this latter test procedure, a copper rod and an iron rod are kept in contact with each other under the surface of 200 milliliters of test oil in a beaker for 7 days at a constant temperature of 135°C. On completion of the test it was found that passing ratings were achieved relative to sludge formation, iron rod performance and weight change of the copper rod.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
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GB898929096A GB8929096D0 (en) 1989-12-22 1989-12-22 Metal free lubricants

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EP0572866A1 (de) * 1992-05-30 1993-12-08 Fuchs Petrolub Ag Oel + Chemie Umweltverträgliche und biologisch schnell abbaubare Betriebsstoffe zur Umlaufschmierung von Motoren und sonstigen Aggregaten in Fahrzeugen und Arbeitsmaschinen
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
GB2301113A (en) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Ltd Extreme pressure gear lubricant
US5582760A (en) * 1995-12-22 1996-12-10 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid
US5585029A (en) * 1995-12-22 1996-12-17 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid
US5587355A (en) * 1995-12-22 1996-12-24 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives
EP0780462A2 (de) 1995-12-22 1997-06-25 Exxon Research And Engineering Company Turboöl mit hohen Lastaufnahmeeigenschaften, enthaltend Aminphosphat und Schwefelhaltige Carbonsäure
US5658864A (en) * 1995-03-24 1997-08-19 Ethyl Corporation Biodegradable pour point depressants for industrial fluids derived from biodegradable base oils
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
US5801130A (en) * 1995-12-22 1998-09-01 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
WO1999059958A1 (en) * 1998-05-20 1999-11-25 The Associated Octel Company Limited Biodegradable corrosion inhibitors
WO2001066677A1 (fr) * 2000-03-09 2001-09-13 Ceca S.A. Lubrifiant multifonctionnel a base de composes phosphores et de composes soufres
WO2002092735A1 (en) * 2001-05-11 2002-11-21 Shell International Research Maatschappij B.V. Lubricating oil composition comprising an additive combination of a carboxylic acid and an amine as ant-rust agent
WO2009074664A1 (en) * 2007-12-12 2009-06-18 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
WO2009074667A1 (en) * 2007-12-12 2009-06-18 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
US7888299B2 (en) * 2003-01-15 2011-02-15 Afton Chemical Japan Corp. Extended drain, thermally stable, gear oil formulations

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JP5426829B2 (ja) * 2007-02-07 2014-02-26 昭和シェル石油株式会社 油圧シリンダーのビビリ、振動、鳴き防止用潤滑油組成物
JP5475984B2 (ja) * 2007-12-12 2014-04-16 昭和シェル石油株式会社 潤滑油組成物
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WO2009139433A1 (ja) * 2008-05-14 2009-11-19 協和発酵ケミカル株式会社 油類用添加剤およびこれを含有する潤滑油

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Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5328619A (en) * 1991-06-21 1994-07-12 Ethyl Petroleum Additives, Inc. Oil additive concentrates and lubricants of enhanced performance capabilities
EP0572866A1 (de) * 1992-05-30 1993-12-08 Fuchs Petrolub Ag Oel + Chemie Umweltverträgliche und biologisch schnell abbaubare Betriebsstoffe zur Umlaufschmierung von Motoren und sonstigen Aggregaten in Fahrzeugen und Arbeitsmaschinen
US5275749A (en) * 1992-11-06 1994-01-04 King Industries, Inc. N-acyl-N-hydrocarbonoxyalkyl aspartic acid esters as corrosion inhibitors
EP0596197A1 (de) * 1992-11-06 1994-05-11 King Industries, Inc. N-Acyl,N-hydrocarbyloxyalkyl Asparaginsäurederivat enthaltende Schmiermittelzusammensetzung
US5658864A (en) * 1995-03-24 1997-08-19 Ethyl Corporation Biodegradable pour point depressants for industrial fluids derived from biodegradable base oils
GB2301113A (en) * 1995-05-22 1996-11-27 Ethyl Petroleum Additives Ltd Extreme pressure gear lubricant
US5585029A (en) * 1995-12-22 1996-12-17 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and 2-alkylthio-1,3,4-thiadiazole-5-alkanoic acid
US5750478A (en) * 1995-12-22 1998-05-12 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and sulfurized fatty acid
EP0780461A1 (de) 1995-12-22 1997-06-25 Exxon Research And Engineering Company Turboöl mit hohen Druckaufnahmeeigenschaften, Aminphosphat und eine 2-Alkylthio-1,3,4-Thiadiazo-5-Alkansäure enthaltend
EP0780463A1 (de) 1995-12-22 1997-06-25 Exxon Research And Engineering Company Turboöl mit hohen Druckaufnahmeeigenschaften, Aminphosphat und Derivate von Thiophen-Carbonsäure enthaltend
EP0780462A2 (de) 1995-12-22 1997-06-25 Exxon Research And Engineering Company Turboöl mit hohen Lastaufnahmeeigenschaften, enthaltend Aminphosphat und Schwefelhaltige Carbonsäure
EP0780462A3 (de) * 1995-12-22 1997-07-02 Exxon Research And Engineering Company Turboöl mit hohen Lastaufnahmeeigenschaften, enthaltend Aminphosphat und Schwefelhaltige Carbonsäure
US5582760A (en) * 1995-12-22 1996-12-10 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and alkylthiosuccinic acid
US5679627A (en) * 1995-12-22 1997-10-21 Exxon Research & Engineering Company High-load carrying turbo oils containing amine phosphate and a sulfur containing carboxylic acid (law348)
US5801130A (en) * 1995-12-22 1998-09-01 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and dimercaptothiadiazole derivatives
US5587355A (en) * 1995-12-22 1996-12-24 Exxon Research And Engineering Company High load-carrying turbo oils containing amine phosphate and thiophene carboxylic acid derivatives
US5714441A (en) * 1996-07-12 1998-02-03 Exxon Research And Engineering Company Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
US5856280A (en) * 1996-07-12 1999-01-05 Exxon Research And Engineering Company Sulfur-containing carboxylic acid derivatives to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils
WO1999059958A1 (en) * 1998-05-20 1999-11-25 The Associated Octel Company Limited Biodegradable corrosion inhibitors
WO2001066677A1 (fr) * 2000-03-09 2001-09-13 Ceca S.A. Lubrifiant multifonctionnel a base de composes phosphores et de composes soufres
FR2806094A1 (fr) * 2000-03-09 2001-09-14 Ceca Sa Lubrifiant multifonctionnel a base de composes phosphores et de composes soufres
WO2002092735A1 (en) * 2001-05-11 2002-11-21 Shell International Research Maatschappij B.V. Lubricating oil composition comprising an additive combination of a carboxylic acid and an amine as ant-rust agent
US7888299B2 (en) * 2003-01-15 2011-02-15 Afton Chemical Japan Corp. Extended drain, thermally stable, gear oil formulations
WO2009074664A1 (en) * 2007-12-12 2009-06-18 Shell Internationale Research Maatschappij B.V. Lubricating oil composition
WO2009074667A1 (en) * 2007-12-12 2009-06-18 Shell Internationale Research Maatschappij B.V. Lubricating oil composition

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CA2032940C (en) 2000-07-18
JPH04114097A (ja) 1992-04-15
DE69016976D1 (de) 1995-03-23
ES2067701T3 (es) 1995-04-01
GB2239257A (en) 1991-06-26
GB9027874D0 (en) 1991-02-13
GB8929096D0 (en) 1990-02-28
EP0434464B1 (de) 1995-02-15
DE69016976T2 (de) 1995-06-22
GB2239257B (en) 1994-01-19
CA2032940A1 (en) 1991-06-23
JP2965710B2 (ja) 1999-10-18

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