EP0075478B1 - Borderivat von hydroxylgruppenhaltigen Zusammensetzungen und diese enthaltende Schmiermittel - Google Patents

Borderivat von hydroxylgruppenhaltigen Zusammensetzungen und diese enthaltende Schmiermittel Download PDF

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Publication number
EP0075478B1
EP0075478B1 EP82304950A EP82304950A EP0075478B1 EP 0075478 B1 EP0075478 B1 EP 0075478B1 EP 82304950 A EP82304950 A EP 82304950A EP 82304950 A EP82304950 A EP 82304950A EP 0075478 B1 EP0075478 B1 EP 0075478B1
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EP
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Prior art keywords
diol
composition according
borated
lubricant
composition
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Expired
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EP82304950A
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English (en)
French (fr)
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EP0075478A2 (de
EP0075478A3 (en
Inventor
Andrew Gene Horodysky
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ExxonMobil Oil Corp
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Mobil Oil Corp
ExxonMobil Oil Corp
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Application filed by Mobil Oil Corp, ExxonMobil Oil Corp filed Critical Mobil Oil Corp
Priority to AT82304950T priority Critical patent/ATE28661T1/de
Publication of EP0075478A2 publication Critical patent/EP0075478A2/de
Publication of EP0075478A3 publication Critical patent/EP0075478A3/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
    • C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron compounds
    • 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
    • C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • 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
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C10M2227/062—Cyclic esters
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the invention relates to lubricant compositions containing borated linear hydrocarbyl vicinal termainal diols to reduce friction and fuel consumption in internal combustion engines.
  • a lubricant composition comprising a lubricant and from 0.1 to 10% by weight of a borated linear hydrocarbyl vicinal terminal diol containing from 14 to 20 carbon atoms.
  • Alcohols are well known for their lubricity properties when formulated into lubricating oils and fortheir water-scavenging characteristics when blended into fuels.
  • Vicinal hydroxyl-containing alkyl carboxylates such as glycerol monooleate have also found widespread use as lubricity additives.
  • U.S. Patent 2,788,326 describes such esters as glycerol monoleates, as minor components of lubricating oil compositions.
  • U.S. Patent 3,235,498 describes, among others, that same ester as an additive to other oils.
  • U.S. Patent 2,443,578 teaches esters wherein the free hydroxyl group is found in the acid portion as for example in tartaric acid.
  • borated hydrocarbyl vicinal diols As lubricant additives. It is recognised that borated hydrocarbyl and borated aliphatic diols are known for other uses.
  • U.S. Patent 3,740,358 teaches a phenol-aldehyde foamable composition containing a boron compound, e.g. a material formed by reacting boric acid or boric oxide with such aliphatic hydroxyl-containing compound.
  • alkyl terminal vicinal diol borate esters possess much improved solubility characteristics, especially in synthetic fluids, over those of the non-borated derivatives.
  • These borates are non-corrosive to copper, possess anti-oxidant and potential anti-fatigue characteristics.
  • the compositions also have significantly greater friction reducing properties, higher viscosity indices and good low temperature characteristics and solubility characteristics when used in low additive concentrations-than do other known additives.
  • hydrocarbyl vicinal terminal diols contemplated for use in this invention are linear hydrocarbyl diols having vicinal terminal hydroxyls. They have the formula: wherein R is a linear hydrocarbyl group containing 14 to 20 carbon atoms.
  • hydrocarbyl includes, but is not limited to tetradecyl, pentadecyl, hexadecyl, octadecyl, eicosyl and the like.
  • R can be saturated or unsaturated with linear saturated members being preferred to maximize friction reduction.
  • the vicinal terminal diols can be synthesized using several methods known to the art such as that described in J. Am. Chem. Soc., 68,1504 (1946) which involves the hydroxylation of 1-olefins with peracids. Vicinal terminal diols can also be prepared by the peroxytrifluoroacetic acid method for the hydroxylation of olefins as described in J. Am. Chem. Soc., 76, 3472 (1954). Similar procedures can be found in U.S. Patents 2,411,762; 2,457,329; and 2,455,892.
  • the diols can also be prepared via catalytic epoxidation of an appropriate olefin followed by hydrolysis to form the appropriate vicinal diol.
  • the borated vicinal terminal diols contain 14 to 20 carbon atoms. Above a carbon number of 20, solubility constraints become significant. Preferred are the C 14 ⁇ C 17 hydrocarbyl groups in which solubility, frictional characteristics and other properties are maximized.
  • diols contemplated for reaction with the boron compound are 1,2-tetradecanediol, 1,2-pentadecanediol, 1,2-hexadecanediol, 1,2-octadecanediol, 1,2-mixed Cis-C18-alkanediols and mixtures thereof.
  • the boronated compound used in this invention can be made using a single diol or two or more diols.
  • a mixture of diols can contain from about 5% to about 95% by weight of any one diol, the other diol or diols being selected such that it or they together comprise from about 95% to about 5% by weight of the mixture. Such mixtures are often preferred to the single diol.
  • the borated esters are used with lubricating oils to the extent of from 0.1 % to 10% by weight of the total composition.
  • other additives such as detergents, anti-oxidants, anti-wear agents may be present. These can include phenates, sulfonates, succinimides, zinc dithiophosphates, polymers, calcium and magnesium salts.
  • the lubricants contemplated for use with the esters herein disclosed include mineral and synthetic hydrocarbon oils of lubricating viscosity mixtures of mineral oils and synthetic oils and greases from any of these, including mixtures.
  • the synthetic hydrocarbon oils include long-chain alkanes such as cetanes and olefin polymers such as oligomers of hexane, octene, decene, and dodecene, etc. These vicinal diols are especially effective in synthetic oils formulated using mixtures of synthetic hydrocarbon olefin oligomers and lesser amounts of hydrocarbyl carboxylate ester fluids.
  • the other synthetic oils which can be used alone with the borated compounds of this invention, or which can be mixed with a mineral or synthetic hydrocarbon oil, include (1) fully esterified ester oils, with no free hydroxyls, such as pentaerythritol esters of monocarboxylic acids having 2 to 20 carbon atoms, trimethylolpropane esters of monocarboxylic acids having 2 to 20 carbon atoms, (2) polyacetals and (3) siloxane fluids.
  • Especially useful among the synthetic esters are those made from polycarboxylic acids and monohydric alcohols.
  • ester fluids made by fully esterifying pentaerythritol, or mixtures thereof with di- and tripentaerythritol, with an aliphatic monocarboxylic acid containing from 1 to 20 carbon atoms, or mixtures of such acids.
  • thickening agents can be used in the greases of this invention. Included among the thickening agents are alkali and alkaline earth metal soaps of fatty acids and fatty materials having from 12 to 30 carbon atoms per molecule.
  • the metals are typified by sodium, lithium, calcium and barium.
  • Fatty materials are illustrated by stearic acid, hydroxystearic acid, stearin, cottonseed oil acids, oleic acid, palmitic acid, myristic acid and hydrogenated fish oils.
  • thickening agents include salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent No. 2,197,263), barium stearate acetate (U.S. Patent No. 2,564,561), calcium stearate-caprylateacetate complexes (U.S. Patent No. 2,999,065), calcium caprylate-acetate (U.S. Patent No. 2,999,066), and calcium salts and soaps of low-, intermediate- and high-molecular weight acids and of nut oil acids.
  • salt and salt-soap complexes as calcium stearate-acetate (U.S. Patent No. 2,197,263), barium stearate acetate (U.S. Patent No. 2,564,561), calcium stearate-caprylateacetate complexes (U.S. Patent No. 2,999,065), calcium caprylate-acetate (U.S. Patent No. 2,999,066), and calcium salts and soaps of low
  • Another group of thickening agents comprises substituted ureas, phthalocyanines, indanthrene, pigments such as perylimides, pyromellitdiimides, and ammeline.
  • the preferred thickening gelling agents employed in the grease compositions are essentially hydrophobic clays.
  • Such thickening agents can be prepared from clays which are initially hydrophilic in character, but which have been converted into a hydrophobic condition by the introduction of long chain hydrocarbon radicals into the surface of the clay particles; prior to their use as a component of a grease composition, as, for example, by being subjected to a preliminary treatment with an organic cationic surface active agent, such as an onium compound.
  • Typical onium compounds are tetraalkylammonium chlorides, such as dimethyl dioctadecyl ammonium chloride, dimethyl dibenzyl ammonium chloride and mixtures thereof.
  • the clays which are useful as starting materials in forming the thickening agents to be employed in the grease compositions can comprise the naturally occurring chemically unmodified clays.
  • These clays are crystalline complex silicates, the exact composition of which is not subject to precise description, since they vary widely from one natural source to another.
  • These clays can be described as complex inorganic silicates such as aluminum silicates, magnesium silicates, barium silicates, and the like, containing, in addition to the silicate lattice, varying amounts of cation-exchangeable groups such as sodium.
  • Hydrophilic clays which are particularly useful for conversion to desired thickening agents include montmorillonite clays, such as bentonite, attapulgite, hectorite, illite, saponite, sepiolite, biotite, vermiculite, zeolite clays, and the like.
  • the thickening agent is employed in an amount from 0.5 to 30, and preferably from 3 percent to 15, percent by weight of the total grease composition.
  • Solvents that can be used include the hydrocarbon solvents, such as toluene, benzene, xylene, and the like, alcohol solvents such as propanol, butanol, pentanol and the like, as well as mixtures of hydrocarbon solvents or alcohol solvents and mixtures of hydrocarbon and alcohol solvents.
  • hydrocarbon solvents such as toluene, benzene, xylene, and the like
  • alcohol solvents such as propanol, butanol, pentanol and the like, as well as mixtures of hydrocarbon solvents or alcohol solvents and mixtures of hydrocarbon and alcohol solvents.
  • the products of the Examples were blended into a fully formulated 5W-20 synthetic automotive engine oil containing other additives, such as detergent, dispersant, anti-oxidant and the like additives and evaluated using the Low Velocity Friction Apparatus (LVFA) test.
  • LVFA Low Velocity Friction Apparatus
  • the compounds were evaluated as friction modifiers in accordance with the following test.
  • the Low Velocity Friction Apparatus is used to measure the friction of test lubricants under various loads, temperatures, and sliding speeds.
  • the LVFA consists of a flat SAE 1020 steel surface (diam. 3.8 cm.) which is attached to a drive shaft and rotated over a stationary, raised, narrow ringed SAE 1020 steel surface of 51.6 mm 2 (area 0.08 in. 2 ). Both surfaces are submerged in the test lubricant. Friction between the steel surfaces is measured as a function of the sliding speed at a lubricant temperature of 121°C. The friction between the rubbing surfaces is measured using a torque arm-strain gauge system.
  • the strain gauge output which is calibrated to be equal to the coefficient of friction, is fed to the Y axis of an X-Y plotter.
  • the speed signal from the tachometer-generator is fed to the X-axis.
  • the piston is supported by an air bearing.
  • the normal force loading the rubbing surfaces is regulated by air pressure on the bottom of the piston.
  • the drive system consists of an infinitely variable- speed hydraulic transmission driven by a 373W (1/2 HP) electric motor. To vary the sliding speed, the output speed of the transmission is regulated by a lever-cam motor arrangement.
  • test lubricant The rubbing surfaces and 12-13 ml of test lubricant are placed on the LVFA. A 1756 kPa (240 psig) load is applied, and the sliding speed is maintained at 12.2 m/s (40 fpm) at ambient temperature for a few minutes. A plot of coefficients of friction (U k ) over the range of sliding speeds, 1.5 to 12.2 m/s (5 to 40 fpm, 25-195 rpm), is obtained. A minimum of three measurements is obtained for each test lubricant. Then, the test lubricant and specimens are heated to 121°C, another set of measurements is obtained, and the system is run for 50 minutes at 121°C, 240 psi and 12.2 m/s (40 fpm) sliding speed.
  • U k coefficients of friction
  • the data obtained are shown in Table 1.
  • the data in Table 1 are reported as percent reduction in coefficient of friction at two speeds.
  • the friction reducing ester additives were evaluated in a fully formulated 5W-20 synthetic lubricating oil comprising an additive package including anti-oxidant, detergent and dispersant.
  • the oil had the following general characteristics:
  • the products of this invention were tested in a catalytic oxidation test for lubricants, using as the base oil a 200" solvent paraffinic neutral mineral oil.
  • the test lubricant composition is subjected to a stream of air bubbled through the composition at a rate of 5 liters per hour at 163°C for 40 hours.
  • Present in the composition are metals commonly used as materials of engine construction, namely:
  • Inhibitors for oil are rated on the basis of prevention of oil deterioration as measured by the increase in acid formation or neutralization number (NN) and kinematic viscosity (KV) occasioned by the oxidation. The results of the tests are reported in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Claims (10)

1. Schmiermittel, enthaltend einen Schmierstoff und 0,1 bis 10 Gew.-% eines borierten linearen Kohlenwasserstoffs in Form eines vicinalen terminalen Diols mit 14 bis 20 Kohlenstoffatomen.
2. Mittel nach Anspruch 1, worin das Diol 1,2-Tetradecandiol, 1,2-Pentadecandiol, 1,2-Hexadecandiol, 1,2-Octadecandiol oder 1,2-Eikosandiol ist.
3. Mittel nach Anspruch 1 oder 2, worin das Diol 1,2-(Gemischt-C15―C18)-alkandiole sind.
4. Mittel nach Anspruch 1, worin der Kohlenwasserstoffrest 14 bis 17 Kohlenstoffatome hat.
5. Mittel nach einem der Ansprüche 1 bis 4, worin das Diol ein Gemisch aus Diolen mit 5 bis 95 Gew.-% eines Diols ist.
6. Mittel nach einem der Ansrpüche 1 bis 5, worin das Diol mit einer Verbindung der Formel
Figure imgb0007
boriert wurde, worin R einen Ci-C6-Alkylrest, x eine Zahl von 0 bis 3 und y eine Zahl von 0 bis 3 bedeuten sowie die Summe aus x und y die Zahl 3 beträgt.
7. Mittel nach Anspruch 6, worin die Verbindung Borsäure ist.
8. Mittel nach einem der Ansprüche 1 bis 7, worin mindestens 5 bis 10% der zur Verfügung stehenden Hydroxylgruppen des Diols boriert worden sind.
9. Mittel nach einem der Ansprüche 1 bis 8, worin das borierte Diol 0.1 bis 10 Gew.-% Bor enthält.
10. Mittel nach einem der Ansprüche 1 bis 9 worin der Schmierstoff ein Mineralschmieröl, ein synthetisches Schmieröl, ein Gemisch davon oder ein daraus hergestelltes Fett umfaßt.
EP82304950A 1981-09-22 1982-09-21 Borderivat von hydroxylgruppenhaltigen Zusammensetzungen und diese enthaltende Schmiermittel Expired EP0075478B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82304950T ATE28661T1 (de) 1981-09-22 1982-09-21 Borderivat von hydroxylgruppenhaltigen zusammensetzungen und diese enthaltende schmiermittel.

Applications Claiming Priority (2)

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US30448281A 1981-09-22 1981-09-22
US304482 1981-09-22

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EP0075478A2 EP0075478A2 (de) 1983-03-30
EP0075478A3 EP0075478A3 (en) 1983-09-21
EP0075478B1 true EP0075478B1 (de) 1987-07-29

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EP (1) EP0075478B1 (de)
JP (1) JPS5865792A (de)
AT (1) ATE28661T1 (de)
AU (1) AU553247B2 (de)
BR (1) BR8205535A (de)
CA (1) CA1198726A (de)
DE (1) DE3276869D1 (de)
NZ (1) NZ201613A (de)
ZA (1) ZA825972B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1191502A (en) * 1981-10-26 1985-08-06 Vernon R. Small, Jr. Method for reducing brake noise in oil-immersed disc brakes
EP0204039A1 (de) * 1985-06-05 1986-12-10 Mobil Oil Corporation Borierte, hydrolisierte Epoxide und Schmiermittelzusammensetzungen, die sie enthalten
US4961868A (en) * 1983-01-10 1990-10-09 Mobil Oil Corporation Grease composition
NZ206931A (en) * 1983-08-03 1986-12-05 Mobil Oil Corp Grease compositions containing borated epoxide derivatives and sulphur and phosphorus-containing compounds
US5084194A (en) * 1984-03-07 1992-01-28 Mobil Oil Corporation Grease composition
US4780227A (en) * 1984-08-22 1988-10-25 Mobil Oil Corporation Grease composition containing borated alkoxylated alcohols
NZ213008A (en) * 1984-08-22 1989-04-26 Mobil Oil Corp Grease compositions containing diol/boron compound reaction products
US4781850A (en) * 1985-08-27 1988-11-01 Mobil Oil Corporation Grease compositions containing borated catechol compounds and hydroxy-containing soap thickeners
US4655948A (en) * 1985-08-27 1987-04-07 Mobil Oil Corporation Grease compositions containing borated catechol compounds and hydroxy-containing soap thickeners
US4828734A (en) * 1985-08-27 1989-05-09 Mobil Oil Corporation Grease compositions containing borated oxazoline compounds and hydroxy-containing soap thickeners
DE3662891D1 (en) * 1985-10-24 1989-05-24 Ciba Geigy Ag Boric-acid complexes
AU2003293266B2 (en) * 2002-12-06 2009-07-02 The Lubrizol Corporation Molybdenum-containing lubricant for improved power or fuel economy
US7419515B2 (en) * 2005-08-10 2008-09-02 Advanced Lubrication Technology, Inc. Multi-phase distillate fuel compositions and concentrates containing emulsified boric acid
CN101874102B (zh) * 2007-09-26 2015-02-18 卢布里佐尔公司 作为润滑剂中的添加剂的钛化合物和络合物
US9388362B2 (en) * 2012-10-30 2016-07-12 Chevron Oronite Company Llc Friction modifiers and a method of making the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795548A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2741548A (en) * 1954-10-15 1956-04-10 Standard Oil Co Leaded motor fuel containing boron compounds
NL112783C (de) * 1956-04-09
US3076013A (en) * 1958-03-24 1963-01-29 Standard Oil Co Process for preparing a complex mixture of aliphatic glycol borates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795548A (en) * 1954-06-29 1957-06-11 California Research Corp Lubricant compositions

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AU8801682A (en) 1983-03-31
ATE28661T1 (de) 1987-08-15
DE3276869D1 (en) 1987-09-03
AU553247B2 (en) 1986-07-10
JPS5865792A (ja) 1983-04-19
JPH0328478B2 (de) 1991-04-19
BR8205535A (pt) 1983-08-30
EP0075478A2 (de) 1983-03-30
CA1198726A (en) 1985-12-31
ZA825972B (en) 1984-03-28
NZ201613A (en) 1985-09-13
EP0075478A3 (en) 1983-09-21

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