US3720615A - Oil-soluble rust preventive composition - Google Patents

Oil-soluble rust preventive composition Download PDF

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US3720615A
US3720615A US00061850A US3720615DA US3720615A US 3720615 A US3720615 A US 3720615A US 00061850 A US00061850 A US 00061850A US 3720615D A US3720615D A US 3720615DA US 3720615 A US3720615 A US 3720615A
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oil
carbon atoms
acid
amine
rust preventive
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K Izumi
T Watanabe
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Kao Corp
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Kao Corp
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/22—Acids obtained from polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/288—Partial esters containing free carboxyl groups
    • C—CHEMISTRY; METALLURGY
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    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • 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
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • 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
    • C10M2215/28—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/088—Neutral salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/063—Ammonium or amine salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
    • 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
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • An oil-soluble rust preventive composition consists essentially of (A) a polycarboxylic acid having seven to 44 carbon atoms and 2 or 3 carboxyl groups or a partial ester of said acid with analiphatic alcohol having one to 18 carbon atoms and (B) an aliphatic tertiary amine having three hydrocarbon groups, each of which has at least one to 20 carbon atoms and at least one of which has six to 20 carbon atoms.
  • the weight ratio of (A) to (B) is in the range of 95:5 to 5:95.
  • This invention relates to an oil-soluble rust preventive composition and, more particularly, it relates to a binary rust preventive composition suitable for use in hydrocarbon oils such as fuel oils or lubricant oils.
  • rust preventives are employed together with sludge-dispersants or detergent-dispersants.
  • Conventionally known rust preventives for instance, higher aliphatic amines, carboxylates such as sodium alkylmercapto acetate, sulfonates such as petroleum calcium sulfonate, phosphates such as zinc dithiophosphonate and partial esters of polyhydric alcohols such as sorbitane monooleate have, however, poor demulsibility against dispersants used in combination therewith, particularly dispersants of the metal salt type, such as metal sulfonates.
  • the object of the present invention is to provide a composition which exhibits an excellent rust preventive property, when added to hydrocarbon oils.
  • Another object of this invention is to provide an oilsoluble rust preventive composition having a good demulsibility.
  • the polycarboxylic acids to be used in the composition according to the present invention include alkenyl succinic acids, such as polyisobutenyl succinic acids having a polyisobutenyl group of 1-8 polymerization degree (four to 32 carbon atoms in the alkenyl group) and polyisopropenyl succinic acids having a polyisopropenyl group of 1-10 polymerization degree (three to 30 carbon atoms in the alkenyl group), unsaturated fatty acid-maleic anhydride addition products having 16-22 carbon atoms (which are also called maleated fatty acids), and, in general compounds with 7-44 carbon atoms possessing two or three carboxyl groups in a molecule such as dimerized fatty acids.
  • the aliphatic alcohols to be used for the partial esterification of these polycarboxylic acids are those which possess one-18 carbon atoms.
  • dimerized fatty acids are dimers of poly-unsaturated fatty acids having six-22 carbon atoms, for instance, dimers of dienoic acids such as sorbic acid (C palmitoleic acid (C linolic acid (C and eicosanoic acid (C and dimers of trienoic acids such as linoleic acid (C and eleostearic acid (C,,,).
  • dimers of dienoic acids such as sorbic acid (C palmitoleic acid (C linolic acid (C and eicosanoic acid (C and dimers of trienoic acids such as linoleic acid (C and eleostearic acid (C,,,).
  • the above-described unsaturated fatty acid-maleic anhydride addition products can be prepared by mixing monoenoic acids such as oleic acid, dienoic acids such aslinolic acid or trienoic acids such as linoleic acid with maleic anhydride with heating. This procedure is well known and is described, for example, in Progress in the Chemistry of Fats and Other Lipids", Vol. 5,
  • the addition product ob tained is a compound of the Diels-Alder type represented by the following formula, for instance, with linolic acid:
  • the tertiary fatty amines to be used in the present invention are fatty amines possessing three hydrocarbon groups, each having l-20 carbon atoms, and at least one hydrocarbon group of which has 6-20 carbon atoms: for instance, there may be exemplified hexyldipentyl amine, octyldiisobutyl amine, decyldiisobutyl amine, dodecyldiethyl amine, octadecyldimethyl amine, octadecyldiisopropyl amine, ethyldihexyl amine, methyldioctyl amine, methylhexadecyloctadecyl amine, methyldioctadecyl amine, trioctyl amine, trihexyl amine, tridecyl amine,
  • polycarboxylic acids or tertiary amines to be used in this invention have been already known as rust preventives when used separately, but the composition of the present invention is prepared by blending them to accomplish a synergistic rust preventive effect as well as to extend further the application fields in which rust preventives could be successfully used and to improve their demulsibility to dispersants of the metal salt type.
  • the blending ratio of the polycarboxylic acid vs. tertiary amine should be in the range :5 to 5:95 by weight. Mixtures outside of this range cannot achieve the desired synergistic rust preventive effect and demulsibility to dispersants.
  • the rust preventive composition of this invention is usually used in an amount in the range of about 0.001 to 3 percent by weight, based on the weight of the hydrocarbon oil in which it is used.
  • the hydrocarbon oils in which the rust preventive composition is used include lubricating oils consisting of mixtures of paraffinic, olefinic, aromatic or naphthenic hydrocarbons having carbon numbers of 4 to 100, which have generally specific gravities (15/4C) of 0.75 to 1.05 and viscosities (100F) of 3 to 20,000 cst, and fuel oils such as kerosene, diesel fuel oils, gas oils and heavy fuel oils.
  • SAE No. 300 oil (commercially sold under the name of 500 neutral oil) and hydrotreated (hydrogen-treated) 100 neutral oil have following properties:
  • representative dispersants to be used in combination with rust preventives include alkenyl succinimides, bisalkenyl succinimides, trisalkenyl succinimides, alkaline earth metal salts of alkyl benzene sulfonate, alkaline metal salts of sulfurized alkyl phenol and alkaline earth metal salts of alkyl sulfonate.
  • the preferred alkaline earth metal salts are calcium and barium.
  • oxidation and bearing corrosion inhibitor such as zinc or amine salts of dialkyl dithio phosphonate, bis-(di or tri alkyl phenols) phenols and alkyl monoor polysulfides can be added in the amount of 0.1 to 5.0 percent by weight based on the base oil.
  • oilness improver such as fatty acids (C to C fatty acid esters (esters of fatty acid of C to C with alcohol of C to C and fatty amines of C to C can be used in the amount of 0.5 to percent by weight based on the base oil.
  • EXAMPLE 1 A sample oil was prepared by dissolving 0.2 percent by weight of a mixture of maleated oleic acid (A) and trioctyl amine (B) as a testing rust preventive in a hydrogen-treated 100-neutral base oil, and the rust preventive and demulsibility properties of the sample oil were examined.
  • samples A B Base oil Rust Rating The samples Nos. 3 and 4 are compositions according to the present invention, and a synergistic effect is obviously recognized, as compared with those of Nos. 1 and 2. s 2. Demulsibility Following the testing method for demulsibility of turbine oil, according to MS K-2520, the demulsibility of the sample oils Nos. 3, 4 and 5 in Table l was examined. The results are shown in Table 2.
  • EXAMPLE 2 The rust preventive property and the demulsibility were examined for the following various rust preventive compositions.
  • Diiaohutylene succinic hexyldipentyl acid mine 25 Diisobutylene succinic Trioctyl amine acid 26 Te taisopropylene succinic Trihexyl amine act 27 lsopropylene succinic acid Octyldiiaobutyl amine 28 lsobutylene succinic acid Ethyldiheayl amine 29 Tetraiaobutylene succinic Methyldioctyl acid amine 30 Octaisopropylene succinic Tridodecyl ac amine 3i Maleated oleic acid Trioctade cyl amme 32 Maleated methyl oleate Decyldiiaopropyl amine 33 Dimer acid of C (85% Octadecyldimethyl dimer acid) mine b.
  • test piece was hung in a closed plastic testing box having 2N hydrochloric acid at the bottom thereof. Then it was allowed to stand at 25C for 24 hours in the HCl-H,O vapor and taken out. The oil was washed off with benzine gently so as not to disturb the surface condition of the test piece. After coating the surface of the test piece with clear lacquer, the sample was rated comparing the color with the standard color chart, 10 being the best and 0 being the poorest.
  • the sample oil was prepared by dissolving 0.2 percent by weight of each of the above-described samples Nos. 1 to 40 in hydrogen-treated 100 neutral base oil.
  • the base oil containing only 0.2 percent by weight of Ca-sulfonate dissolved therein leaves a considerable emulsion layer even 75 minutes after the mixing, while the demulsibility is a little improved by adding carboxylic acid or its partial ester and it is greatly improved by adding further aliphatic tertiary amine.
  • An oil composition consisting essentially of a hydrocarbon lubricating oil or fuel oil containing from about 0.001 to 3 percent by weight of an oil-soluble rust preventive composition consisting essentially of A. material selected from the group consisting of l) alkenyl succinic acids having three to 32 carbon atoms in the alkenyl substituent, (2) unsaturated monoenoic, dienoic or trienoic fatty acid-maleic anhydride addition products having 16 to 22 carbon atoms and their lower alkanol esters, (3) dimers of polyunsaturated dienoic and trienoic fatty acids having six to 22 carbon atoms, and B.
  • A. material selected from the group consisting of l) alkenyl succinic acids having three to 32 carbon atoms in the alkenyl substituent, (2) unsaturated monoenoic, dienoic or trienoic fatty acid-maleic anhydride addition products having 16 to 22 carbon atoms and their lower alkanol esters, (3) dimers of poly
  • the balance of the composition is a hydrocarbon lubricating or fuel oil, said dispersant being present in an amount less than about 15 percent by weight of said oil composition.
  • An oil soluble rust preventive composition having good demulsibility consisting essentially of A. the addition product of maleic anhydride and a monoenoic fatty carboxylic acid having 16 to 22 carbon atoms, and
  • An oil composition consisting essentially of a hydrocarbon lubricating oil or fuel oil containing from about 0.001 to 3 percent by weight of an oil-soluble rust preventive composition consisting essentially of A. the addition product of maleic anhydride and a monoenoic fatty carboxylic acid having 16 to 22 carbon atoms, and I B. an aliphatic tertiary amine having three hydrocarbon groups, each of which has from one to 20 carbon atoms, and at least one of which has six to 20 carbon atoms,
  • the weight ratio of (A) to (B) being in the range of 95:5 to 5:95, and the balance of the composition is a hydrocarbon lubricating oil or fuel oil.

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  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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US00061850A 1969-08-11 1970-08-06 Oil-soluble rust preventive composition Expired - Lifetime US3720615A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936480A (en) * 1971-07-08 1976-02-03 Rhone-Progil Additives for improving the dispersing properties of lubricating oil
FR2311839A1 (fr) * 1975-05-23 1976-12-17 Cooper Ltd Ethyl Nouvelle huile lubrifiante contenant un inhibiteur de corrosion pour moteur a combustion interne
US4049562A (en) * 1976-04-15 1977-09-20 Chevron Research Company Extreme pressure lubricant compositions
US4162223A (en) * 1978-03-21 1979-07-24 Phillips Petroleum Company Residue of hydrogenation product of branched aliphatic dinitriles as lubricant additive
US4589992A (en) * 1983-10-19 1986-05-20 Ciba-Geigy Corporation New salts useful as corrosion inhibitors
US4737159A (en) * 1984-06-29 1988-04-12 E. I. Du Pont De Nemours And Company Corrosion inhibitor for liquid fuels
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WO2002100988A3 (en) * 2001-06-08 2003-02-20 Exxonmobil Res & Eng Co Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
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FR2311839A1 (fr) * 1975-05-23 1976-12-17 Cooper Ltd Ethyl Nouvelle huile lubrifiante contenant un inhibiteur de corrosion pour moteur a combustion interne
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US4737159A (en) * 1984-06-29 1988-04-12 E. I. Du Pont De Nemours And Company Corrosion inhibitor for liquid fuels
US5273672A (en) * 1987-03-02 1993-12-28 Idemitsu Kosan Company Limited Lubricating oil composition containing a partial ester of a polyhydric alcohol and a substituted succinic acid ester
US5064546A (en) * 1987-04-11 1991-11-12 Idemitsu Kosan Co., Ltd. Lubricating oil composition
US5549847A (en) * 1991-04-24 1996-08-27 Ciba-Geigy Corporation Flowable aqueous dispersions of polycarboxylic acid corrosion inhibitors
US5958089A (en) * 1995-02-02 1999-09-28 Exxon Chemical Patents, Inc. Additives and fuel oil compositions
US6280488B1 (en) 1995-02-02 2001-08-28 Exxon Chemical Patents Inc Additives and fuel oil compositions
WO2000015739A1 (en) * 1998-09-14 2000-03-23 The Lubrizol Corporation Diesel fuel compositions
US6051039A (en) * 1998-09-14 2000-04-18 The Lubrizol Corporation Diesel fuel compositions
US6677281B2 (en) * 2001-04-20 2004-01-13 Exxonmobil Research And Engineering Company Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
WO2002100988A3 (en) * 2001-06-08 2003-02-20 Exxonmobil Res & Eng Co Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
AU2002322031B2 (en) * 2001-06-08 2007-06-14 Exxonmobil Research And Engineering Company Synergistic combination of metallic and ashless rust inhibitors to yield improved rust protection and demulsibility in dispersant-containing lubricants
US20050192185A1 (en) * 2004-02-27 2005-09-01 Saathoff Lee D. Power transmission fluids
US7947636B2 (en) * 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
US20120053101A1 (en) * 2010-09-01 2012-03-01 Baker Hughes Incorporated Functionalized Maleated Fatty Acids as Non Acidic Fluid Additives

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ES382545A1 (es) 1972-12-01

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