US3719600A - Lubricant composition containing polycarboxylic acid - Google Patents

Lubricant composition containing polycarboxylic acid Download PDF

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Publication number
US3719600A
US3719600A US00113741A US3719600DA US3719600A US 3719600 A US3719600 A US 3719600A US 00113741 A US00113741 A US 00113741A US 3719600D A US3719600D A US 3719600DA US 3719600 A US3719600 A US 3719600A
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acid
parts
lubricating oil
lubricant composition
oil
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US00113741A
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D Bosniack
H Shaub
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
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    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
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    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • 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
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • 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
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02—Unspecified siloxanes; Silicones
    • 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
    • C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/04—Siloxanes with specific structure
    • C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
    • 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
    • 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
    • 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
    • C10N2040/12—Gas-turbines
    • 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
    • C10N2040/12—Gas-turbines
    • C10N2040/13—Aircraft turbines
    • 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

  • the synthetic lubricating oils which may be improved by use of this invention may include liquid, high molecular weight esters, fluorocarbons, polyethers, and polysilicones, etc.
  • the synthetic oil may be an ester formed by the reaction of (a) a C -C aliphatic acid R (COOH), wherein R is an aliphatic hydrocarbon (including inertly-substituted hydrocarbon) residue and n is typically l3,,preferably l, with (b) a C -C aliphatic alcohol R"(0l-I)m wherein R" is an aliphatic hydrocarbon (including inertyl-sub'stituted hydrocarbon) residue and m is an integer, preferably 1-6, more preferably 14, most preferably 3-4.
  • R a C -C aliphatic acid
  • R is an aliphatic hydrocarbon (including inertly-substituted hydrocarbon) residue and n is typically l3,,preferably l
  • R"(0l-I)m wherein R" is an aliphatic hydrocarbon (including inertyl-sub'stituted hydrocarbon) residue and m is an integer, preferably 1-6,
  • the lubricant composition of this invention may comprise:
  • a a lubricating oil; and 7 b. a corrosion-inhibiting amount of a polycarboxylic acid of the formula R cooH'
  • R is an acyclic hydrocarbyl nucleus having at least four carbon atoms and x is an integer greater than 2.
  • the lubricating oils which may be irn proved by this invention may include various lubricating oils such-as naturally-
  • the base oil may, in one embodiment, be a liquid ester product of an aliphatic monocarboxylic acid and a polyol.
  • the preferred of these acids may be C -C ll-, lustrative of such acids may be:
  • valeric C valeric C, pivalic C, dodecanoic C stearic C "eicosanoic C triacontanoic C hexatriacontanoic C
  • C6-C acids may be used. Typically of such acid may be:
  • caproic acid C caprylic acid C, capric acid C enanthic acid C, pelargonic acid C Z-ethylhexanoic acid C.
  • the polyols which may be reacted with the noted aliphatic mono'carboxylic acids, to form esters may include R"(OI I)m wherein R" is an aliphatic hydrocarbon moiety and m is an integer preferably 2-6, more preferably 2 4.
  • the preferred polyols may be the C2 00, say C2-C4 polyols. Typical may be:
  • neopentyl glycol trimethylol ethane trimethylol propane trimethylol butane pentaerythritol dipentaerythritol
  • Thepreferred glycol may be pentaerythritol.
  • esters may be pentaerythritol tetracaproate.
  • the liquid synthetic ester may be the product of reaction of an aliphatic polycarboxylic acid and an aliphatic monohydroxy alcohol.
  • the aliphatic polycarboxylic acid may have the formula R"(COOI-l)n wherein n is greater than 1 and preferably 2-3.
  • Typical polycarboxylic acids may include:
  • Preferred acids may be adipic and azelaic.
  • the alcohol may have the formula R"OI-I where R" may be a saturated aliphatic group which may be inertly substituted.
  • Typical alcohols may include methanol, n-butanol, 2-ethyl-n-butanol, pentanol,l-hexanol, 2-ethyl-hexanol, l-decanol, 2-ethyloctanol, and 2-ethoxy ethanol.
  • oils may be blended with other synthetic-esters as noted supra or with other oils, such as caster oil; lard oil; polymerized olefins; copolymers of alkylene glycols or aliphatic alcohols with organic acids, etc.
  • the lubricant compositions of the present invention may preferably contain other additives, typically present in amount of 0.001 wt. %,including:
  • oxidation inhibitors such as aromatic amines e.g.
  • phenothiazine Y b. metal corrosion inhibitors such as benzo-triazole; c. metal passivating and load-carrying agents, such as tricresyl phosphate; d. anti-foamants such as a silicone;
  • dispersants such as the polymethacrylates.
  • the corrosion-inhibiting amount of polycarboxylic acid may be sufficient to decrease corrosion, and particularly corrosion of lead, by the lubricant composition to a satisfactory level. Commonly, this may mans a reduction-in lead corrosion to a point at which the lubricantc'omposition satisfies specifications such as those set by the U.S. Air Force as for example in MIL-L-7808G. There may be present 0.01 to 1.0 parts, preferably 0.0l5-to 0.5 parts, most preferably 0.02-0.05 parts of polycarboxylic acid per 100 parts of lubricating oil.
  • R(COOI-I), x may be an integer greater than 2, typically 3-7, preferably 3-4, say 3;
  • R may be a hydrocarbyl moiety containing at least four carbon atomsQtypicaIly an alkyl group.
  • R may be n-butyl, isobutyl, t-butyl, pentyl, neo-pentyl, hexyl, isodecyl, n-octadecyl, 3-ethyl-nonadecyl, etc.
  • the R group may contain inert sub-stituents which are inert under the conditions of operation of the invention, such as aryl, alkaryl, aralkyl, alkoxy, etc. substituents.
  • R of Formula I may be:
  • n is an integer at least four.
  • the acid may be, inter alia, n-octane-l ,2,4,6-tetracarboxylic acid n-decanel ,2,3 ,4-tetracarboxylic acid n-heptane-4-phenyl-l ,4,6,7-tetracarboxylic acid n-pentane-3-ethyl-l -,2,4,5-tetracarboxylic acid, etc.
  • the acid may be, inter alia,
  • the acid is n-pentane-l ,3,5-tricarboxylic acid, (i.e. octric acid).
  • Formula 1 may be an integer greater than 2, typitricarboxylic acid, n-pentane-2,3,4-tricarboxylic acid,
  • This invention may be practiced using mixtures of the above described acids.
  • tricarboxylic acid may be employed.
  • Other such mix tures will be obvious to those skilled in the art.
  • octric acid may be prepared from 4-bromo pimelic acid according to the following scheme:
  • the lubricant composition may be formulated from a concentrate of the polycarboxylic acid.
  • concentrates may contain 0.1 to 50 parts, preferably 0.1-10 parts, say 0.5 to 5 parts of acid in 100 parts of lubricant-composition soluble diluent solvent.
  • the diluent-solvent may be an inert liquid in which the acid may be soluble or dispersible.
  • the solvent may be an inert liquid having a boiling point of about 50--250C., say 75-l50C.
  • the diluent-solvent may be characterized by its solubility or dispersability in lubricants.
  • the diluent-solvent may be a'low molecular weightmineral oil, polyether, a fluorocarbon, or preferably, a lubricating oil.
  • the diluent-solvent may include low molecular weight mineral oils such as solvent 150 neutral oil, solvent 325 neutral oil, and bright stock.
  • Polyethers which may be employed as diluent-solvent include 1,2- dimethoxy ethane; 1,5-diethoxy-3-oxa-pentane; and l,8-diethoxy-3,S-dioxa-octane.
  • Fluorocarbon liquids which may be used as diluent solvents include perfluorooctane, perfluorotetradecane, perfluoro-octadecane and perfluorobenzene.
  • the diluent solvent may be a lubricating oil and most preferably it may be the oil forming the base of the lubricant composition.
  • the concentrates prepared in accordance with this invention may typically contain the following:
  • a preferred concentrate may contain 4 parts acid in 100 parts diluent-solvent.
  • Such concentrates may include:
  • FORMULATION B Component Parts di-2-ethylhexyl adipate di-isodecyl adipate 30 di(octylphenyl )arnine 1.0 phenyl nlphu naphthyl amine 0.8 tricrenyl phottphute 0.6 hydroxy terminated ester of linolcit: acid dimer 0.5 alkyl methacrylate n-vinyl pyrrolidone copolymer (MoLwt. 500,000) 1.0
  • additives such as a primary amine of a C tertiary alkyl group, e.g.
  • Additive B a mixed methyl, butyl phosphate ester salt of an alkylated aryl, amine
  • Results are reported as milligrams lost (or gained) per square inch of exposed plate.
  • the specification requires that an acceptable formulation exhibit a maximum of 25 mg/in LOSS (or gain) after 48 hrs. Storage.
  • the novel compositions of this invention permit attainment'of outstanding results when subjected to this test.
  • the lubricant composition permits lubrication or rubbing parts by contacting a first part to be lubricated with said lubricant composition, and rubbing said part against a second part.
  • example octric 0.025 0.89 7 example octric 0.02 0.04 3.05 8 example octric 0.02 0.02 9 example octric 0.05 0.05
  • Example 20 As can be seen from comparison of Example 17 with Example 18, Example 21 with Example 22 and Example 23 with Example 24, the addition of octric acid to an oil desirably reduces its corrosivity towards lead by as much as a factor of 2000-fold.
  • Use of sebacic acid on the other hand (Example 20) was found to be less than half as effective as octric acid (Example 19).
  • Example Acid 29 n-butane-l ,2,3-tricarboxylic acid 30 3-methy1-pentane 1,3,5-tricarboxylic acid 31 n-heptane-l ,4,7-tricarboxylic acid 32 S-phenyl-n-nonane 1,5,9-tricarboxylic acid
  • Example 33 A concentrate prepared in accordance with this invention may be prepared by adding 0.1 2.0 parts of octric acid to parts of di-(2-ethyl hexyl) azelate and adding 0.0] to 0.2 part of this concentrate to the Formulation A described above.
  • a lubricant composition comprising:
  • a lubricant composition as claimed in claim 1 wherein said acid is of the formula wherein n is an integer between 4 and 21.
  • a lubricant composition comprising:
  • a concentrate for treating lubricant compositions which comprises a. l to 100 parts of a lubricating oil, and
  • a concentrate as claimed in claim 7 wherein the acid is pentane 1,3,5-carboxylic acid.
  • a concentrate for treating lubricant compositions comprising a. about 95.0 99.9 parts of a synthetic ester lubricating oil, and b. about 0.1 5.0 parts of a polycarboxylic acid of the formula R(COOH)

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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)
US00113741A 1971-02-08 1971-02-08 Lubricant composition containing polycarboxylic acid Expired - Lifetime US3719600A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909429A (en) * 1973-03-08 1975-09-30 Continental Oil Co Cutting oil composition
US4042515A (en) * 1974-08-16 1977-08-16 B. V. Beverolfabrieken Anhydrous deep-drawing lubricant
US5064547A (en) * 1990-09-12 1991-11-12 Century Laboratories, Incoporated Lubricant compositions for metals containing dicarboxylic acids as a major constituent
US5240629A (en) * 1992-01-10 1993-08-31 Ethyl Corporation Refrigerant compositions
US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1189181A (fr) * 1981-05-08 1985-06-18 Stephane Guerillot Procede et dispositif pour la recreation d'un signal analogique de luminance a partir d'un signal numerique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1289064A (fr) * 1960-05-04 1962-03-30 British Petroleum Co Composition de graissage liquide

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3909429A (en) * 1973-03-08 1975-09-30 Continental Oil Co Cutting oil composition
US4042515A (en) * 1974-08-16 1977-08-16 B. V. Beverolfabrieken Anhydrous deep-drawing lubricant
US5064547A (en) * 1990-09-12 1991-11-12 Century Laboratories, Incoporated Lubricant compositions for metals containing dicarboxylic acids as a major constituent
US5240629A (en) * 1992-01-10 1993-08-31 Ethyl Corporation Refrigerant compositions
US6043199A (en) * 1997-08-26 2000-03-28 Exxon Research And Engineering Co. Corrosion inhibiting additive combination for turbine oils

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FR2124532A1 (enExample) 1972-09-22

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