US3914179A - Synthetic lubricants for aero gas turbines - Google Patents

Synthetic lubricants for aero gas turbines Download PDF

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Publication number
US3914179A
US3914179A US459765A US45976574A US3914179A US 3914179 A US3914179 A US 3914179A US 459765 A US459765 A US 459765A US 45976574 A US45976574 A US 45976574A US 3914179 A US3914179 A US 3914179A
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United States
Prior art keywords
group
carbon atoms
lubricating composition
alkyl
phosphate
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US459765A
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English (en)
Inventor
Derek Clark Byford
Anthony Arnold John Mundye
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BP PLC
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BP PLC
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Priority to GB02842/67A priority Critical patent/GB1180390A/en
Priority to NL6803664.A priority patent/NL156184B/xx
Priority to FR1558117D priority patent/FR1558117A/fr
Priority to DE1968B0097146 priority patent/DE1644869B2/de
Priority to CH403168A priority patent/CH507359A/de
Priority to BE712471D priority patent/BE712471A/xx
Application filed by BP PLC filed Critical BP PLC
Priority to US459765A priority patent/US3914179A/en
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Publication of US3914179A publication Critical patent/US3914179A/en
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04—Mixtures of base-materials and additives
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    • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
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    • C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
    • C10M129/26—Carboxylic acids; Salts thereof
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    • C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
    • C10M129/42—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms polycarboxylic
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    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
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    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2219/108—Phenothiazine
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    • C10M2229/02—Unspecified siloxanes; Silicones
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    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08—Resistance to extreme temperature
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
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    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/015—Dispersions of solid lubricants
    • C10N2050/02—Dispersions of solid lubricants dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy

Definitions

  • a lubricant suitable for all the current specifications for turbine engines for supersonic transport aircraft is [52] 252/325; g/ 2 based on a hindered ester (e.g. PB 520) and contains 1k 1' t' t' 'd t, 51 int. c1. ..Cl0M 1/44;C10M 3/38; 22 g g ;gg ii fg igz gg ffi g z f fi Field of Search CIOM of a dialkyl hydrogen phosphate as load carrying addifives. 3 3?
  • This invention relates to synthetic lubricants suitable for use under the severe conditions that exist in the op eration of modern aero gas turbine engines. More specifically, the invention is concerned with a lubricant of this type that is based on a thermally stable ester and which contains an additive package principally designed to impart good high temperature anti-oxidation, anti-corrosion, load carrying and hydrolytic stability properties to the basestock.
  • a variation of this procedure uses a temperature of 425F (213C) and a test period of 48 hours.
  • oils having poor resistance to oxidation at high temperature give high viscosity and acidity increase and tend to corrode certain of the metals, especially copper and magnesium.
  • a further problem that is encountered in lubricants of this type is the problem of hydrolytic stability. This problem has been found to arise particularly in lubricants containing phosphates, e.g., tritolyl phosphate, especially when certain metal deactivators are present.
  • One method of assessing the hydrolytic stability of an oil is to store a mixture of the oil and water at C with periodic agitation. The acidity of the oil is determined at intervals and the result may be reported either in terms of the acidity after a certain period of time, or as the time taken to reach a particular level of acidity.
  • the object of the present invention is to provide a lubricating composition of low initial acidity having outstanding oxidation stability, corrosion resistance, hydrolytic stability and load-carrying ability, good low temperature fluidity, and which is clean in use, whereby it is suitable in these respects for the lubrication of modern aero gas turbine engines.
  • a particular object of the invention is to provide a lubricating composition which meets or approaches all the varying such requirements of current (March 1968) specifications for turbine engines for supersonic transport aircraft.
  • a lubricating composition comprising an ester basestock consisting of a liquid neutral polyester that has been prepared by reacting together under esterification conditions and in one or more stages i. an aliphatic monoand/or polyhydric alcohol having 5 10, preferably 5 8, carbon atoms per molecule and having no hydrogen atoms attached to any carbon atom in a 2 position with respect to any 3 OH group and ii. an aliphatic monoand/or polycarboxylic acid having 3 12 carbon atoms per molecule, the basestock having dissolved therein:
  • a. l to 8 preferably 2 to 6, more preferably 3 to 5, wt of an alkylated aromatic amine antioxidant, particularly one where the alkyl groups have up to 14 carbon atoms,
  • a neutral organic phosphate of the formula (RO) ;PO where the groups R are tolyl, phenyl or xylyl groups or alkyl, alkaryl or cycloalkyl groups having up to 10 carbon atoms, and
  • a neutral salt of a dialkyl hydrogen phosphate of the formula (RO) P(O)OH where R is an alkyl or cycloalkyl group having up to 10 carbon atoms, e.g. butyl or cyclohexyl, and an amine, preferably one having not more than 30 carbon atoms, especially a primary amine.
  • the lubricant described above has excellent oxidation stability, corrosion resistance, hydrolytic stability and load carrying properties. Its load carrying properties can be still further improved without substantial impairement of its hydrolytic stability by the addition of 0.005 t 0.2, preferably 0.01 to 0.1, wt of a dialkyl phosphite of the formula (R O) P(O)H where R is an alkyl or cycloalkyl group having up to carbon atoms, e.g. butyl or cyclohexyl.
  • the hydrolytic stability of the compositions according to the invention may be still further improved by the addition of 0.005 to 0.5, preferably 002 to 0.1, wt of a hydrolytic stability improver.
  • Suitable ones are aliphatic or aliphatic/aromatic amines having up to 30 carbon atoms, or hydroxyl derivatives thereof, preferably tertiary amines.
  • the most suitable amines for this purpose are those of the general formula R(R )NR where R and R are alkyl groups having 1 to 4 carbon atoms and R is an alkaryl, or hydroxy-substituted alkaryl, group having up to carbon atoms.
  • a preferred compound of this type is 2.6-ditertiarybutyl- 4-dimethylaminomethyl phenol.
  • Dispersant polymer additives for lubricating oils are well-known materials and suitable ones include acrylate and methacrylate polymers, co-polymers of N-vinyl pyrrolidone with acrylates and methacrylates, and co-polymers of N-vinyl pyrrolidone with olefins as described in UK Pat. Specification No. 1,085,375.
  • the polymers or co-polymers must of course be soluble in the ester basestock.
  • the most suitable ones usually have molecular weights within the range 1000 to 1,000,000, especially 5000 to 500,000.
  • the acrylates and methacrylates referred to are preferably those derived from acrylic or methacrylic acid and monohydric alcohols having 1 to 24, especially 4 to 18, carbon atoms.
  • a lead corrosion inhibitor in the blend, usually at a concentration of 0.01 to 1.0, preferably 0.05 to 0.25, wt.
  • Suitable lead corrosion inhibitors are C, to C 4 alkyl gallates, neopentylglycol disebacate, sebacic acid and quinizarin. Propyl gallate is preferred.
  • the additive concentrations quoted in this specification are based on the ester basestock. It is to be understood that the composition may contain more than one member of each of the classes of ingredients specified.
  • the base oil is a hindered polyester of the type described above.
  • polyester is meant an ester having at least two ester linkages per molecule; it therefore includes diesters such as neopentyl glycol dipelargonate and di(2:2:4-trimethylpentyl) sebacate.
  • diesters such as neopentyl glycol dipelargonate and di(2:2:4-trimethylpentyl) sebacate.
  • neutral is used to mean a fully esterified product.
  • acids and alcohols examples include caprylic acid, capric acid, caproic acid, enanthic acid, pelargonic acid, valeric acid, pivalic acid, propionic acid, butyric acid, 2-ethylhexanoic acid, adipic acid, sebacic acid, azelaic acid, 2;2:4-trimethylpentanol, neopentyl, alcohol, neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol.
  • polyesters are the esters of trimethylolpropane, trimethylolbutane, trimethylolethane,
  • the trimethylolpropane and dicarboxylic acid are reacted in the molar ratio of l 0.05 to 0.75, preferably 1 0.075 to 0.4, the amount of monocarboxylic acid being sufficient to provide a carboxyllhydroxyl balance in the reactants.
  • THE ANTIOXIDANT Suitable alkylated aromatic amine antioxidants are those of the formula R C H NHC l-LR where the groups R are alkyl groups having up to 14 carbon atoms (not necessarily the same in any given molecule), preferably octyl or nonyl groups. p,p'-Dioctyldiphenylamine is particularly effective.
  • Other suitable alkylated aromatic amines include the monoand di- C, to C alkyl phenyl naphthylamines, phenothiazines, iminodibenzyls and diphenyl phenylenediamines, particularly those in which the alkyl groups are octyl or nonyl groups.
  • a two-component antioxidant consisting of a blend of i. an alkylated phenyl naphthylamine, particularly a monoor di- C to C alkyl phenyl naphthylamine, e.g. monoor dioctyl or a monoor dinonyl phenyl naphthylamine, and
  • an alkylated diphenylamine particularly a monoor di- C to C alkyl diphenylamine, e.g., a dioctyl or .dinonyl diphenylamine.
  • the weight of component (ii) that is used is between 1 and 10, especially between 2 and 4, times the weight of component (i) that is used.
  • the alkylated diphenylamine is used because of its cleanness in use and longlasting quality. p,p-Dioctyldiphenylamine is particularly preferred.
  • alkylated diphenylamine antioxidants in accelerated oxidation tests is boosted by an alkylated phenyl naphthylamine, preferably a mono-octyl phenyl naphthylamine.
  • the combination has been found to be very satisfactory for the control of viscosity increase during oxidation tests and gives rise to negligible weights of sludge.
  • Copper passivators are a well-known class of materials, the function of which is to reduce the extent to which metals are corroded by corrosive substances.
  • the copper passivator used in the compositions according to the invention must, of course, be soluble in the basestock. The effect of this additive is to reduce the corrosion on engine components containing copper when exposed to the lubricant for long periods of time at high temperatures and in the presence of air.
  • the effectiveness of metal passivators can be measured by the oxidation/corrosion tests described previously. Copper is the most critical metal involved in such tests and it has been found that if this metal can be effectively passivated, then the corrosion of the other metals present is negligibly small, with the exception of lead.
  • Suitable classes of copper passivator include:
  • Those of the azole type such as imidazole, pyrazole, criazole and their derivatives, e.g. benzotriazole, methylbenzotriazole, ethylbenzotriazole, butylbenzotriazole, dodecylbenzotriazole, methylene bis benzotriazole and naphthotriazole.
  • Salicylaldehyde semicarbazone and its C to C alkyl derivatives e.g. methyl and isopropyl Salicylaldehyde semicarbazone.
  • a particularly suitable hydrazine derivative is aminoguanidine and suitable fatty acids are those having 2 to 24 carbon atoms.
  • Particularly effective copper passivators are methylene bisbenzotriazole and salts of lsalicylalaminoguanidine and fatty acids having 13 to 18 carbon atoms, e.g., palmitic acid.
  • a lead corrosion inhibitor in the blend as described previously.
  • THE LOAD CARRYING ADDlTlVES the main load carrying additive within the previously specified limits and adding a very small amount of the booster (d), above i.e. the amine salt ofa dialkyl hydrogen phosphate.
  • This additive if used in the absence of the neutral phosphate (0) has only a limited effect on the load carrying properties of the lubricant if used at the low concentration specified but at this concentration in combination with the main load-carrying additive (c) it causes an unexpectedly high increase in load carrying properties.
  • the amine salt appears to suppress the hydrolytic decomposition of the phosphate additive (c) and thereby improve the hydrolytic stability of the blend.
  • the amine salt (d) has the further advantage that, being neutral, it enables a low initial acidity of the blend to be achieved more easily than when using a dialkyl hydrogen phosphate as a load carrying booster as described in co-pending UK Pat. Application No. 32739/66 corresponding to US. Pat. Application Ser. No. 652,727 and its continuation application Ser. No. 139,180, both of said applications now being abandoned.
  • Tritolyl phosphate is the preferred main load-carrying additive (c) but other effective ones are triphenyl phosphate, phenyl/tolyl phosphates, trixylyl phosphate, tributyl phosphate, tricyclohexyl phosphate and hindered alkyl phosphates, e.g. tri(tertiarybutylphenyl) phosphate and tri(2,2-dimethy1pentyl) phosphate.
  • Suitable amines that may be used for preparing the neutral amine salt of dialkyl hydrogen phosphate are laurylamine, tetraethylene amine, aniline, the naphthylamines, aminoguanidine, diphenylamine, alkylated diphenylamines (e.g. dioctyl diphenylamine) and N- ethylaniline. Laurylamine is preferred.
  • an anti-foam agent may be included in the composition, e.g. a silicone.
  • composition X is similar to composition A but the laurylammonium dibutyl phosphate of A has been replaced by 0.02% wt of dibutyl hydrogen phosphate (C H O) P(O)OH and the dicyclohexyl phosphite has been replaced by 0.05 wt of dibutyl phosphite (C H O) P(O)H.
  • Base oil P A complex ester made by esterifying caprylic acid, 1 l l-trimethylolpropane and sebacic acid in the molar ratio of 28 l0 1.
  • Base oil Q A complex ester made by esterifying caprylic acid, 1 1 1- trimethylolpropane and sebacic acid in the molar ratio of 10.7 4.23 :1.
  • Base Oil R A blend of 4 parts by weight of a neutral ester of pentaerythritol and a mixture of C to C straight-chain monocarboxylic acids with one part by weight of a neutral ester of dipentaerythritol and the same mixture of acids.
  • Base oil S An ester made by esterifying pentaerythritol, enanthic acid and 2-ethylhexanoic acid in the molar ratio of 1 3 1.
  • the additives used in the compositions were as follows:
  • oils A to F have much N-vmylpylmhdme and a higher load carrying ability than oils J to M and oils A methacrylate (molecular F f d d h h weight 60,000 to 70.000)
  • Sold to are in act inten e to meet or approac t e rec om egc ly lg the name 10 quirements (as at present understood) of the latest cry Hydrolytic stability improver:
  • BMAMP 2:6ditertiarybutyl-4 Bnllsh Speclficanons f advanced ae ro Olls dimethylaminowhich call for much higher load carrying ability than methylphem' the American specification.
  • compositions had the physical properties shown in Table 2.
  • composition of Table 3 (equivalent to composition B of said Appli- T test was earned as dsscnbed prevfously cation No. 32741/66).
  • Composition Y meets both the usmg a temperatur'e of 425 F 2 a test Penod of load carrying and oxidation/corrosion requirements of 48 hours and an of 5 [mes/hourthe British specifications but it will be seen that it is T l are table 3 f Shows the outside the oxidation/corrosion limits of the American desirable limits for 0115 of the type in question.
  • Lead Corrosion Test This was measured by maintaining a sample of the oil at 375F (190C) for 5 hours with air bubbling through it at a rate of 28 litres per hour and with a copper plate immersed in the oil. A lead plate is rotated in the oil and the weight loss after the -test is measured. A good oil of the type in question is considered to be one which gives a weight loss not exceeding 6.0 mg/sq. in. Results are given in Table 6.
  • a lubricating composition comprising an ester basestock consisting of a liquid neutral polyester that has been prepared by reacting together under esterit'lcation conditions and in at least one stage i. an aliphatic alcohol selected from the group consisting of monohydric alcohols, polyhydric alcohols, and mixtures thereof, said alcohol having 5 to 10 carbon atoms per molecule and having no hydrogen atoms attached to any carbon atom in a 2 position with respect to any OH group and ii. an aliphatic acid selected from the group consisting of monocarboxylic acid, polycarboxylic acid, and mixtures thereof, said acid having 3-12 carbon atoms per molecule,
  • an alkylated aromatic amine antioxidant selected from the group consisting of mono-C to C alkyl phenyl naphthylamines di-C to C alkyl phenyl naphthylamines,
  • a copper passivator selected from the group consisting of azole, derivatives thereof, salicylaldehyde semicarbazone, C to C alkyl derivatives thereof, condensation products of salicylaldehyde and hydrazine derivatives, and fatty acid salts of such condensation products,
  • a neutral organic phosphate -of the formula (RO) PO where the groups R are tolyl, phenyl or xylyl groups or alkyl groups having up to 10 carbon atoms or cycloalkyl groups having up to 10 carbon atoms, and
  • a neutral salt of a dialkyl hydrogen phosphate of the formula (RO) P(O)OH where R is an alkyl group having up to 10 carbon atoms or a cycloalkyl group having up to 10 carbon atoms, and an amine having not more than 30 carbon atoms.
  • a lubricating composition comprising an ester basestock consisting of a liquid neutral polyester that has been prepared by reacting together under esterification conditions and in at least one stage i. an aliphatic alcohol selected from the group consisting of monohydric alcohols, polyhydric alcohols, and mixtures thereof, said alcohol having 5 to carbon atoms per molecule and having no hydrogen atoms attached to any carbon atom in a 2 position with respect to any OH group and ii. an aliphatic acid selected from the group consisting of monocarboxylic acid, polycarboxylic acid, and mixtures thereof, said acid having 3-12 carbon atoms per molecule,
  • an alkylated aromatic amine antioxidant selected from the group consisting of mono-C, to C alkyl phenyl naphthylamines, diC to C alkyl phenyl naphthylamines, phenothiazines, iminodibenzyls and diphenyl phenylenediamines, and mixtures of the foregoing,
  • a copper passivator selected from the group consisting of azole, derivatives thereof, salicylaldehyde semicarbazone, C, to C alkyl derivatives thereof, condensation products of salicylaldehyde and hydrazine derivatives, and fatty acid salts of such condensation products,
  • the polyester in which the polyester is a complex ester prepared from (a) trimethylolpropane, (b) a dibasic acid selected from the group consisting of sebacic acid, azelaic acid, and mixtures of said acids and (c) one or more monocarboxylic acids having 3 to 10 carbon atoms.
  • ii a compound selected from the group consisting of a mono-C to C alkyl diphenylamine and a di-C to C alkyl diphenylamine, the amount of (i) being 0.5 to 4.5% wt and of (ii) being 2.0 to 6.0% wt.
  • component (i) is selected from the group consisting of mono-octyl phenyl naphthylamine, di-octyl phenyl naphthylamine, mono-nonyl phenyl naphthylamine and di-nonyl phenyl naphthylamine
  • component (ii) is selected from the group consisting of dioctyl diphenylamine and dinonyl diphenylamine.
  • component (b) is selected from the group consisting of methylene benzotriazole, benzotriazole, methyl benzotriazole, ethyl benzotriazole, a salt of lsalicylalaminoguanidine, with at least one fatty acid having 13 to 18 carbon atoms, and mixtures of the foregoing, the weight of (b) being 0.005 to 0.5%.
  • additive (c) is selected from the group consisting of tritolylphosphate, triphenyl phosphate, a phenyl/tolyl phosphate phosphate mixture, trixylyl phosphate, tributyl phosphate, tricyclohexyl phosphate and a hindered alkyl phosphate, the weight of (0) being 0.5 to 3.5%.
  • component (d) is a neutral salt of dibutyl or dicyclohexyl hydrogen phosphate and an amine selected from the group consisting of laurylamine, tetraethylene amine, aniline, a naphthylamine, aminoguanidine, diphenylamine, an alkylated diphenylamine and N-ethylaniline, the weight of (d) being 0.01 to 0.1%.
  • dialkylphosphite is selected from the group consisting of dibutyl phosphite and dicyclohexyl phosphite, the amount being 0.01 to 0.1% wt.
  • a lubricating composition according to claim 1 which also contains 0.01 to 5.0% wt of a dispersant polymer selected from the group consisting of acrylate polymers, methacrylate polymers, co-polymers of N- vinyl pyrrolidone with acrylates and methacrylates, and co-polymers of N-vinyl pyrrolidone with an olefin.
  • a dispersant polymer selected from the group consisting of acrylate polymers, methacrylate polymers, co-polymers of N- vinyl pyrrolidone with acrylates and methacrylates, and co-polymers of N-vinyl pyrrolidone with an olefin.
  • a lubricating composition according to claim 1 which also contains 0.01 to 1.0% wt of a lead corrosion inhibitor selected from the group consisting of C to C alkyl gallates, neopentylglycol disebacate, sebacic acid 13 and quinizarin.
  • a lead corrosion inhibitor selected from the group consisting of C to C alkyl gallates, neopentylglycol disebacate, sebacic acid 13 and quinizarin.
  • a lubricating composition according to claim 1 which also contains 0.005 to 0.5% wt of a hydrolytic stability improver, said improver being an amine having the general formula R (R )NR where R and R are alkyl groups having 1 to 4 carbon atoms and R is an alkaryl, or hydroxy-substituted alkaryl, group having up to 20 carbon atoms.
  • a hydrolytic stability improver said improver being an amine having the general formula R (R )NR where R and R are alkyl groups having 1 to 4 carbon atoms and R is an alkaryl, or hydroxy-substituted alkaryl, group having up to 20 carbon atoms.
  • a lubricating composition according to claim 16 in which the hydrolytic stability improver is present in the amount of 0.02 to 0.1% wt.
  • a lubricating composition comprising an ester basestock consisting of a liquid neutral polyester prepared by reacting (a) one molar proportion of trimethylolpropane, (b) 0.075 to 0.4 molar proportions of a dibasic acid selected from the group consisting of sebacic acid and azelaic acid, and (c) sufficient of one or more monocarboxylic acids having 3 to 10 carbon atoms to provide a hydroxyl/carboxyl balance in reactants, the said polyester having dissolved therein:
  • a naphthylamine selected from the group consisting of mono-octyl phenyl naphthylamine, di-octyl phenyl naphthylamine, monononyl phenyl naphthylamine, di-nonyl phenyl naphthylamine, and mixtures of the foregoing,
  • a lubricating composition comprising an ester basestock consisting of a liquid neutral polyester prepared by reacting pentaerythritol, either alone or in admixture with up to 50% by weight of di-pentaerythritol, with the stoichiometric amount of one or more monocarboxylic acids having 3 to 10 carbon atoms, the said polyester having dissolved therein:

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US459765A 1967-03-20 1974-04-10 Synthetic lubricants for aero gas turbines Expired - Lifetime US3914179A (en)

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Application Number Priority Date Filing Date Title
GB02842/67A GB1180390A (en) 1967-03-20 1967-03-20 Synthetic Lubricants for Aero Gas Turbines
NL6803664.A NL156184B (nl) 1967-03-20 1968-03-14 Werkwijze ter bereiding van een smeermiddel op basis van een synthetische smeerolie.
FR1558117D FR1558117A (en:Method) 1967-03-20 1968-03-18
DE1968B0097146 DE1644869B2 (de) 1967-03-20 1968-03-19 Schmiermittel
CH403168A CH507359A (de) 1967-03-20 1968-03-19 Synthetische Schmiermittel
BE712471D BE712471A (en:Method) 1967-03-20 1968-03-20
US459765A US3914179A (en) 1967-03-20 1974-04-10 Synthetic lubricants for aero gas turbines

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US17131271A 1971-08-12 1971-08-12
US459765A US3914179A (en) 1967-03-20 1974-04-10 Synthetic lubricants for aero gas turbines

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Cited By (25)

* Cited by examiner, † Cited by third party
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US3986965A (en) * 1975-10-31 1976-10-19 Monsanto Company Ester base lubricating compositions having improved oxidative resistance
US4053424A (en) * 1976-03-15 1977-10-11 Texaco Inc. Grease containing synergistic extreme pressure additives
US4130494A (en) * 1976-05-05 1978-12-19 Exxon Research & Engineering Co. Synthetic lubricant composition
US4197210A (en) * 1977-04-22 1980-04-08 Mobil Oil Corporation Oil-soluble adducts of benzotriazole and dialkylamines and lubricant compositions containing the same
US4224172A (en) * 1978-12-04 1980-09-23 Mobil Oil Corporation Oil-soluble adducts of benzotriazole and oxazolines and lubricant compositions containing same
US4313840A (en) * 1979-03-07 1982-02-02 Agency Of Industrial Science And Technology Heat transfer oil and method for driving a Freon turbine
US4335006A (en) * 1979-05-31 1982-06-15 Uniroyal, Inc. Method of stabilizing lubricating fluids
US4440657A (en) * 1982-09-01 1984-04-03 Exxon Research And Engineering Co. Synthetic ester lubricating oil composition containing particular t-butylphenyl substituted phosphates and stabilized hydrolytically with particular long chain alkyl amines
US4701273A (en) * 1983-12-23 1987-10-20 Ciba-Geigy Corporation Lubricant compositions containing antioxidants, amine phosphates and 4- (5-) methyl-1-[di-(2-ethylhexyl) aminomethyl]-benzotriazole
US4734209A (en) * 1984-04-04 1988-03-29 Ciba-Geigy Corporation Metal deactivators
US4877541A (en) * 1987-12-11 1989-10-31 Exxon Research And Engineering Company Corrosion inhibitor
US5334320A (en) * 1990-06-29 1994-08-02 Tonen Corporation Compositions for hydraulic, lubricating and coupling
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
US5650088A (en) * 1995-03-24 1997-07-22 Nippon Mining & Metals Company, Ltd. Treating solution for gold-plated material
EP0877074A3 (de) * 1997-05-07 1999-12-15 OMV Aktiengesellschaft Schmieröl auf Esterbasis und Verwendung von Inhibitoren gegen Metallauflösung in demselben
US6194359B1 (en) * 1996-11-16 2001-02-27 Fragol Schmierstoff Gmbh & Co. Kg Operating fluid for lifetime lubricated internal combustion engines
US6468946B2 (en) 1998-07-06 2002-10-22 The Lubrizol Corporation Mixed phosphorus compounds and lubricants containing the same
EP1344769A1 (en) 2002-03-13 2003-09-17 BP Corporation North America Inc. Polyol ester derivatives of polyamines and their use as dispersants for lubricating oils
US20090093384A1 (en) * 2007-10-03 2009-04-09 The Lubrizol Corporation Lubricants That Decrease Micropitting for Industrial Gears
WO2010079744A1 (ja) * 2009-01-09 2010-07-15 株式会社ジャパンエナジー 潤滑油組成物
WO2011084657A1 (en) * 2009-12-17 2011-07-14 The Lubrizol Corporation Lubricating composition containing an aromatic compound
US20120322706A1 (en) * 2010-01-18 2012-12-20 Jx Nippon Oil & Energy Corporation Lubricating oil composition
JP2014055284A (ja) * 2012-08-16 2014-03-27 Cosmo Oil Lubricants Co Ltd タービン油組成物
US9481841B2 (en) 2004-12-09 2016-11-01 The Lubrizol Corporation Process of preparation of an additive and its use
WO2025088375A1 (en) * 2023-10-27 2025-05-01 Infineum International Limited Lubricant compositions containing high c9 disubstituted diphenylamine antioxidant content

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GB1357744A (en) * 1971-03-31 1974-06-26 Exxon Research Engineering Co Antioxidants

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US3321401A (en) * 1964-09-18 1967-05-23 British Petroleum Co Lubricating compositions
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US3247109A (en) * 1962-04-23 1966-04-19 Chevron Res Lubricant compositions
US3247111A (en) * 1963-04-08 1966-04-19 Socony Mobil Oil Co High temperature jet lubricant
US3265618A (en) * 1963-07-26 1966-08-09 Shell Oil Co Lubricating oil compositions
US3347791A (en) * 1964-02-26 1967-10-17 Eastman Kodak Co Antioxidant composition and ester lubricating oil containing it
US3321401A (en) * 1964-09-18 1967-05-23 British Petroleum Co Lubricating compositions

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986965A (en) * 1975-10-31 1976-10-19 Monsanto Company Ester base lubricating compositions having improved oxidative resistance
US4053424A (en) * 1976-03-15 1977-10-11 Texaco Inc. Grease containing synergistic extreme pressure additives
US4130494A (en) * 1976-05-05 1978-12-19 Exxon Research & Engineering Co. Synthetic lubricant composition
US4197210A (en) * 1977-04-22 1980-04-08 Mobil Oil Corporation Oil-soluble adducts of benzotriazole and dialkylamines and lubricant compositions containing the same
US4224172A (en) * 1978-12-04 1980-09-23 Mobil Oil Corporation Oil-soluble adducts of benzotriazole and oxazolines and lubricant compositions containing same
US4313840A (en) * 1979-03-07 1982-02-02 Agency Of Industrial Science And Technology Heat transfer oil and method for driving a Freon turbine
US4335006A (en) * 1979-05-31 1982-06-15 Uniroyal, Inc. Method of stabilizing lubricating fluids
US4440657A (en) * 1982-09-01 1984-04-03 Exxon Research And Engineering Co. Synthetic ester lubricating oil composition containing particular t-butylphenyl substituted phosphates and stabilized hydrolytically with particular long chain alkyl amines
US4701273A (en) * 1983-12-23 1987-10-20 Ciba-Geigy Corporation Lubricant compositions containing antioxidants, amine phosphates and 4- (5-) methyl-1-[di-(2-ethylhexyl) aminomethyl]-benzotriazole
US4734209A (en) * 1984-04-04 1988-03-29 Ciba-Geigy Corporation Metal deactivators
US4877541A (en) * 1987-12-11 1989-10-31 Exxon Research And Engineering Company Corrosion inhibitor
US5334320A (en) * 1990-06-29 1994-08-02 Tonen Corporation Compositions for hydraulic, lubricating and coupling
US5650088A (en) * 1995-03-24 1997-07-22 Nippon Mining & Metals Company, Ltd. Treating solution for gold-plated material
US5560848A (en) * 1995-05-26 1996-10-01 Exxon Research And Engineering Company Combination diphenyl amine-phenothiazine additive for improved oxidation stability in polyol ester based greases (Law236)
US6194359B1 (en) * 1996-11-16 2001-02-27 Fragol Schmierstoff Gmbh & Co. Kg Operating fluid for lifetime lubricated internal combustion engines
EP0877074A3 (de) * 1997-05-07 1999-12-15 OMV Aktiengesellschaft Schmieröl auf Esterbasis und Verwendung von Inhibitoren gegen Metallauflösung in demselben
US6468946B2 (en) 1998-07-06 2002-10-22 The Lubrizol Corporation Mixed phosphorus compounds and lubricants containing the same
EP1344769A1 (en) 2002-03-13 2003-09-17 BP Corporation North America Inc. Polyol ester derivatives of polyamines and their use as dispersants for lubricating oils
US9481841B2 (en) 2004-12-09 2016-11-01 The Lubrizol Corporation Process of preparation of an additive and its use
US20090093384A1 (en) * 2007-10-03 2009-04-09 The Lubrizol Corporation Lubricants That Decrease Micropitting for Industrial Gears
JP5693240B2 (ja) * 2009-01-09 2015-04-01 Ｊｘ日鉱日石エネルギー株式会社 潤滑油組成物
WO2010079744A1 (ja) * 2009-01-09 2010-07-15 株式会社ジャパンエナジー 潤滑油組成物
CN102272276A (zh) * 2009-01-09 2011-12-07 吉坤日矿日石能源株式会社 润滑油组合物
US9150813B2 (en) 2009-12-17 2015-10-06 The Lubrizol Corporation Lubricating composition containing an aromatic compound
US9279093B2 (en) 2009-12-17 2016-03-08 The Lubrizol Corporation Lubricating composition containing an aromatic compound
WO2011084657A1 (en) * 2009-12-17 2011-07-14 The Lubrizol Corporation Lubricating composition containing an aromatic compound
EP2527420A4 (en) * 2010-01-18 2013-08-14 Jx Nippon Oil & Energy Corp OIL COMPOSITION
US20120322706A1 (en) * 2010-01-18 2012-12-20 Jx Nippon Oil & Energy Corporation Lubricating oil composition
US9296976B2 (en) * 2010-01-18 2016-03-29 Jx Nippon Oil & Energy Corporation Lubricating oil composition
JP2014055284A (ja) * 2012-08-16 2014-03-27 Cosmo Oil Lubricants Co Ltd タービン油組成物
WO2025088375A1 (en) * 2023-10-27 2025-05-01 Infineum International Limited Lubricant compositions containing high c9 disubstituted diphenylamine antioxidant content
EP4545621A3 (en) * 2023-10-27 2025-06-18 Infineum International Limited Lubricant compositions containing high c9 disubstituted diphenylamine antioxidant content

Also Published As

Publication number Publication date
DE1644869B2 (de) 1978-01-05
NL6803664A (en:Method) 1968-09-23
DE1644869A1 (de) 1970-09-24
BE712471A (en:Method) 1968-09-20
FR1558117A (en:Method) 1969-02-21
NL156184B (nl) 1978-03-15
GB1180390A (en) 1970-02-04
CH507359A (de) 1971-05-15

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