EP0134063B1 - Composition de graisse - Google Patents

Composition de graisse Download PDF

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Publication number
EP0134063B1
EP0134063B1 EP84300933A EP84300933A EP0134063B1 EP 0134063 B1 EP0134063 B1 EP 0134063B1 EP 84300933 A EP84300933 A EP 84300933A EP 84300933 A EP84300933 A EP 84300933A EP 0134063 B1 EP0134063 B1 EP 0134063B1
Authority
EP
European Patent Office
Prior art keywords
composition
mixtures
sulfur
phosphorus
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP84300933A
Other languages
German (de)
English (en)
Other versions
EP0134063A3 (en
EP0134063A2 (fr
Inventor
Andrew Gene Horodysky
John Antone Keller, Jr.
John Phillips Doner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp
Priority to AT84300933T priority Critical patent/ATE31425T1/de
Publication of EP0134063A2 publication Critical patent/EP0134063A2/fr
Publication of EP0134063A3 publication Critical patent/EP0134063A3/en
Application granted granted Critical
Publication of EP0134063B1 publication Critical patent/EP0134063B1/fr
Expired legal-status Critical Current

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    • 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
    • C10M169/06—Mixtures of thickeners and additives
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    • C10M113/00—Lubricating compositions characterised by the thickening agent being an inorganic material
    • C10M113/16—Inorganic material treated with organic compounds, e.g. coated
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    • C10M117/02—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen
    • C10M117/04—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen containing hydroxy groups
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    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Semi-solids; greasy

Definitions

  • the invention is concerned with a novel group of compositions. It more particularly relates to a synergistic grease composition comprising grease, metal hydroxy-containing soap thickener, borated epoxide and phosphorus and sulfur moieties.
  • U.S. Patent No. 4,410,438 relates to lubricant compositions, including greases, comprising borated epoxides in which boron is present in excess. Also, certain other forms of epoxides have been used in lubricants. For example, U.S. 4,244,829 describes the use of epoxidized fatty acid esters as lubricity agents in lubricating oils.
  • a grease composition consisting essentially of (1) a major amount of a grease and at least about 15% by weight of a hydroxyl-containing soap thickener (2) from 0.01% to 10% by weight of a reaction product made by reacting an epoxide of the formula wherein R, R', R 2 and R 3 are hydrogen or a hydrocarbyl group containing from 8 to 30 carbon atoms at least 1 of which is hydrocarbyl, with at least a molar amount of a boron compound selected from boric acid, boric oxide and an alkyl borate of the formula wherein x is 1 to 3, y is 0 to 2, their sum being 3, and R 4 is an alkyl group having 1 to 6 carbon atoms and (3) from about 0.01% to about 10% by weight of a phosphorus and sulfur compound or a mixture of phosphorus-containing and sulfur-containing compounds to supply a like amount of phosphorus and sulfur.
  • the borated product contains more than a stiochiometric amount of boron.
  • the borated epoxides of the invention can be made by reacting an epoxide with boron compound, such as boric oxide, boric acid or an alkyl borate, or mixtures thereof.
  • boron compound such as boric oxide, boric acid or an alkyl borate, or mixtures thereof.
  • the resulting products are primarily monoborate esters, but other possible products present are the products of reaction between epoxide dimers, or higher oligomers, and a boron compound to form the corresponding borate esters.
  • 1,2-epoxyoctane 1,2-epoxydecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxyeicosane and mixtures of such epoxides, as well as mixtures of other epoxides.
  • These include epoxides of mixtures of C 22 to C 30 olefins and of mixtures of C 24 to C 28 olefins.
  • Hydrocarbyl is meant to include alkyl, aryl, cycloalkyl or cycloalkenyl groups containing from 8 to 30 carbon atoms, preferably 10 to 22 carbon atoms.
  • hydrocarbyl is an alkyl group.
  • the boron compound used is boric acid, boric oxide or an alkyl borate, preferably boric acid.
  • the alkyl borates include the mono-, di- and trialkyl borates, such as the mono-, di-and triethyl borates.
  • the reaction to form the borate ester can be carried out at from 80°C to 260°C, preferably from 110°C to 180°C.
  • the temperature chosen will depend for the most part on the particular reactants and on whether or not a solvent is used.
  • quantities of reactants be chosen such that the molar ratio of epoxide to boron compound be from 0.2 to 1, preferably from 0.5 to 0.9.
  • the epoxide can be reacted with an excess of the borating species to form a borate ester containing from 0.1 % by weight of boron to more than 10% of boron.
  • reaction can be advantageously run at from 100 to 500 kPa (1 to 5 atmospheres).
  • a solvent may be used.
  • any relatively non-polar, unreactive solvent can be used, including benzene, toluene, xylene and 1,4-dioxane.
  • Other hydrocarbon and alcoholic soluents, which include propanol and butanol can be used. Mixtures of alcoholic and hydrocarbon solvents can be used also.
  • any phase of the process can be carried out in from 1 to 20 hours.
  • a narrow class of thickening agents is preferred to make the grease of this invention. Included among the preferred thickening agents are those containing at least a portion of alkali and alkaline earth metal soaps of hydroxyl-containing fatty acids, fatty glycerides and fatty esters having from 12 to about 30 carbon atoms per molecule.
  • the metals are typified by sodium, lithium, calcium and barium. Preferred is lithium.
  • Preferred members among these acids and fatty materials are 12-hydroxystearic acid and glycerides containing 12-hydroxystearates.
  • the entire amount of thickener need not be derived from the aforementioned preferred members. Significant benefit can be attained using as little thereof as about 15% by weight of the total thickener.
  • a complementary amount such as up to about 85% by weight of a wide variety of thickening agents, can be used in the grease of this invention. Included among the other useful thickening agents are alkali and alkaline earth metal soaps of methyl-1 2-hydroxystea rate, diesters of a C 4 to C 12 dicarboxylic acid and tall oil fatty acids. Other alkali or alkaline earth metal fatty acids containing from 12 to 30 carbon atoms and no free hydroxyl may be used. These include soaps of stearic and oleic acids.
  • 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-caprylate-acetate 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.
  • thickening agents comprises substituted ureas, phthalocyamines, indanthrene, pigments such as perylimides, pyromellitdiimides, and ammeline, as well as certain hydrophobic clays.
  • These 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. This method of conversion, being well known to those skilled in the art, is believed to require no further discussion.
  • the third member(s) of the grease composition of the instant invention are the phosphorus and sulfur moieties. Both of these can be present in the same molecule, such as in a metal or non-metal phosphorothioate or phosphorodithioate of the formula wherein R 5 is a hydrocarbyl group containing 3 to 18 carbon atoms, M is a metal or non-metal, n is the valence of M and X is oxygen or sulfur.
  • R 5 is preferably an alkyl group and may be a propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, octadecyl or oleyl group, including those derived from isopropanol, butanol, isobutanol, sec-butanol, 4-methyl-2-pentanol, 2-ethylhexanol, oleyl alcohol, and mixtures thereof. Further included are alkaryl groups such as butylphenyl, octylphenyl, nonylphenyl and dodecylphenyl groups.
  • the metals covered by M include those in Groups IA, IIA, IIB and VIII of the Periodic Table. Some that may be mentioned are lithium, sodium, calcium, zinc, cadmium, silver and gold.
  • Non-metallic ions include organic groups derived from vinyl esters such as vinyl acetate, vinyl ethers such as butyl vinyl ether and epoxides such as propylene oxide and 1,2-epoxydodecane.
  • the phosphorus and sulfur can also be supplied from the combination of two separate compounds, such as the combination of (1) a dihydrocarbyl phosphite having 2 to 10 carbon atoms in each hydrocarbyl group or mixtures of phosphites and (2) a sulfide such as sulfurized isobutylene, dibenzyl disulfide, sulfurized terpenes, phosphorodithionyl disulfide and sulfurized jojoba oil.
  • the phosphites embrace the dibutyl, dihexyl, dioctyl and didecyl phosphites and mixtures thereof.
  • Phosphate esters containing 4 to 20 carbon atoms in each hydrocarbyl group such as tributyl phosphate, tridecyl phosphate, tricresyl phosphate and mixtures of such phosphates, can also be used.
  • reaction products of the present invention may be employed in any amount which is effective for imparting the desired degree of friction reduction, antiwear activity, antioxidant activity, high temperature stability or antirust activity.
  • berated epoxide and the phosphorus- and/or sulfur-containing compound(s) are effectively employed in combined amounts from 0.02% to 20% by weight, and preferably from 0.2% to 4% of the total weight of the composition.
  • the greases of the present invention can be made from either a mineral oil or a synthetic oil, or mixtures thereof.
  • mineral oils both paraffinic, naphthenic and mixtures thereof, may be of any suitable lubricating viscosity range, as for example, from 5.7 to 1300 mm 2 /s at 38°C (45 SSU at 100°F to 6000 SSU at 100°F), and preferably from 7.4 to 54 mm 2 /s at 99°C (50 to 250 SSU at 210°F).
  • These oils may have viscosity indexes ranging to 100 or higher. Viscosity indexes from 70 to 95 are preferred.
  • the average molecular weights of these oils may range from 250 to 800.
  • the lubricating oil from which it is prepared is generally employed in an amount sufficient to balance the total grease composition, after accounting for the desired quantity of the thickening agent, and other additive components to be included in the grease formulation.
  • Typical synthetic vehicles include polyisobutylene, polybutenes, hydrogenated polydecenes, polypropylene glycol, polyethylene glycol, trimethylol propane esters, neopentyl and pentaerythritol esters, di(2-ethylhexyl) sebacate, di(2-ethylhexyl) adipate, dibutyl phthalate, fluorocarbons, silicate esters, silanes, esters of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl ethers typified by a butyl-substituted bis(p-phenoxy phenyl) ether, phenoxy phenylethers.
  • a lithium hydroxystearate grease thickener was prepared by saponification of 12-hydroxystearic acid (8%) and glyceride (9%) with lithium hydroxide monohydrate (2.5%) in a mineral oil vehicle (about 76%) at about 177°C and final pressure of about 860 kPa (110 psig) in a closed contactor. All percentages were percentages by weight of the total weight of the thickener.
  • a boron ester was added to the grease concentrate.
  • the boron-containing ester was prepared by placing 1440 g of 1,2-epoxyhexadecane, 500 g of toluene and 500 g of boric acid in a glass reactor equipped with heater, agitator and Dean-Stark tube with condenser. The reaction mixture was heated up to 144°C until water evolution as a result of azeotropic distillation ceased. The solvent was removed by vacuum distillation and the crude borate ester was filtered through diatomaceous earth to form a clear amber fluid which became waxy after cooling.
  • the dropping point of the dehydrated thickener without borated epoxide was 199°C. Adding 1.4 wt.% of borated epoxide to the thickener increased the dropping point to 257°C. After the normal grease additive package was added to produce a finished grease, the dropping point increased further to 307°C. The dropping point of an identical, fully formulated finished grease with metallic dithiophosphate but without the borated epoxide was 193°C.

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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)
  • Inorganic Chemistry (AREA)
  • Lubricants (AREA)

Claims (17)

1. Composition de graisse consistant essentiellement: en (1) une grande quantité d'une graisse et au moins environ 15% en poids d'un épaississant du type savon hydroxylé; (2) de 0,01 à 10% en poids d'un produit de réaction préparé par réaction d'un époxyde de formule
Figure imgb0011
dans laquelle R, R', RZ et R3 sont chacun l'hydrogène ou un groupe hydrocarbyle en C8―C30 et dont l'un au moins est un groupe hydrocarbyle, avec au moins une quantité molaire d'un composé de bore choisi parmi l'acide borique, l'oxyde borique et un borate d'alkyle de formule
Figure imgb0012
dans laquelle x est de 1 à 3, y est de 0 à 2, leur somme étant 3, et R4 est un groupe alkyle en C1―C6; et (3) d'environ 0,01 à environ 10% en poids d'un composé de phosphore et de soufre ou d'un mélange de composés phosphorés et soufrés pour fournir une quantité semblable de phosphore et de soufre.
2. Composition selon la revendication 1, dans laquelle l'épaississant est un savon de métal alcalin ou de métal alcalino-terreux d'un acide gras hydroxylé, d'un glycéride gras ou d'un ester gras contenant 12 à 30 atomes de carbone.
3. Composition selon la revendication 2, dans laquelle le métal est le sodium, le lithium, le calcium ou le baryum.
4. Composition selon la revendication 2, dans laquelle l'épaississant dérive de l'acide 12-hydroxy- stéarique.
5. Composition selon la revendication 1, dans laquelle l'époxyde est le 1,2-époxyoctane, le 1,2-époxydécane, le 1,2-époxydodécane, le 1,2-époxytétradécane, le 1,2-époxypentadécane, le 1,2-époxyhexadécane, le 1,2-époxyoctadécane, le 1,2-époxyeicosane, les époxydes de mélanges d'oléfines en C22―C30, les époxydes de mélanges d'oléfines en C24―C28, les époxydes de trimères de décène ou les époxydes de dimères d'octène ou de dimères de décène ou de dimères mixtes d'octène et de décène.
6. Composition selon la revendication 1, dans laquelle les restes phosphorés et soufrés sont fournis par un phosphorothioate ou un phosphorodithioate de formule
Figure imgb0013
dans laquelle RS est un groupe hydrocarbyle en C3―C18, M est un métal ou un reste non métallique, n est la valence de M et X est l'oxygène ou le soufre.
7. Composition selon la revendication 6, dans laquelle RS est un groupe alkyle.
8. Composition selon la revendication 7, dans laquelle RS est un groupe propyle, butyle, pentyle, hexyle, octyle, décyle, dodécyle, tétradécyle, octadécyle ou oléyle ou leurs mélanges.
9. Compositions selon la revendication 8, dans laquelle RS dérive de l'isopropanol, du butanol, de l'isobutanol, du sec-butanol, du 4-méthyl-2-pentanol, du 2-éthylhexanol ou de leurs mélanges.
10. Composition selon la revendication 6, dans laquelle M est un métal du groupe IA, IIA, IIB ou VIII de la Classification Périodique.
11. Composition selon la revendication 10, dans laquelle le métal est le lithium, le sodium, calcium, le zinc, le cadmium ou l'or.
12. Composition selon la revendication 6, dans laquelle M dérive de l'acétate de vinyle, de l'éther butyl-vinylique, de l'oxyde de propylène ou du 1,2-époxydodécane.
13. Composition selon la revendication 1, dans laquelle les restes phosphorés et soufrés sont fournis par une combinaison de (1) un phosphite de dihydrocarbyle ayant de 2 à 10 atomes de carbone dans chaque groupe hydrocarbyle, des mélanges de ces phosphites ou un phosphate d'hydrocarbyle ayant de 4 à 20 atomes de carbone dans chaque groupe hydrocarbyle et (2) un sulfure choisi parmi l'isobutylène sulfuré, le disulfure de dibenzyle, les terpènes sulfurés, le disulfure de phosphorodithionyle et l'huile de jujube sulfurée.
14. Composition selon la revendication 13, dans laquelle le phosphite est un phosphite de dibutyle, de dihexyle, de dioctyle ou de didécyle ou leurs mélanges.
15. Composition selon la revendication 13, dans laquelle l'ester phosphorique est le phosphate de tributyle, de tridécyle ou de tricrésyle ou leurs mélanges.
16. Composition selon la revendication 13, dans laquelle l'époxyde est le 1,2-époxyhexadécane, le composé de bore est l'acide borique et le composé contenant du phosphore et du soufre est un dialkylphosphorodithioate de zinc dans lequel les groupes alkyles dérivent d'un mélange d'alcools secondaire en C3 et primaire en Cs.
17. Composition selon la revendication 1, dans laquelle le véhicule de la graisse est une huile minérale, une huile synthétique ou leurs mélanges. '
EP84300933A 1983-08-03 1984-02-14 Composition de graisse Expired EP0134063B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT84300933T ATE31425T1 (de) 1983-08-03 1984-02-14 Schmierfett-zusammensetzung.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51987883A 1983-08-03 1983-08-03
US519878 1983-08-03

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EP0134063A2 EP0134063A2 (fr) 1985-03-13
EP0134063A3 EP0134063A3 (en) 1985-05-15
EP0134063B1 true EP0134063B1 (fr) 1987-12-16

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EP (1) EP0134063B1 (fr)
JP (1) JPH0662987B2 (fr)
AT (1) ATE31425T1 (fr)
AU (1) AU566667B2 (fr)
BR (1) BR8401750A (fr)
CA (1) CA1209982A (fr)
DE (1) DE3468122D1 (fr)
NZ (1) NZ206931A (fr)
ZA (1) ZA844087B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4582617A (en) * 1983-08-03 1986-04-15 Mobil Oil Corporation Grease composition containing borated epoxide and hydroxy-containing soap grease thickener
US4961868A (en) * 1983-01-10 1990-10-09 Mobil Oil Corporation Grease composition
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
US4781850A (en) * 1985-08-27 1988-11-01 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
US4655948A (en) * 1985-08-27 1987-04-07 Mobil Oil Corporation Grease compositions containing borated catechol compounds and hydroxy-containing soap thickeners
KR20210025753A (ko) * 2019-08-27 2021-03-10 현대자동차주식회사 고온 내구성이 향상된 윤활제 조성물

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DE1256826B (de) * 1957-04-17 1967-12-21 Mobil Oil Corp Schmierfett
AU550869B2 (en) * 1981-08-03 1986-04-10 Chevron Research Company Lubricating oil with borated long chain 1,2 alkane diol friction modifier
NZ201613A (en) * 1981-09-22 1985-09-13 Mobil Oil Corp Lubricant compositions containing borated diols
CA1191502A (fr) * 1981-10-26 1985-08-06 Vernon R. Small, Jr. Methode d'insonorisation des freins a disque sous bain d'huile
US4410438A (en) * 1981-12-11 1983-10-18 Mobil Oil Corporation Borated epoxides and lubricants containing same

Also Published As

Publication number Publication date
EP0134063A3 (en) 1985-05-15
AU566667B2 (en) 1987-10-29
EP0134063A2 (fr) 1985-03-13
BR8401750A (pt) 1985-04-02
ATE31425T1 (de) 1988-01-15
DE3468122D1 (en) 1988-01-28
AU2395484A (en) 1985-02-07
JPS6040200A (ja) 1985-03-02
NZ206931A (en) 1986-12-05
CA1209982A (fr) 1986-08-19
ZA844087B (en) 1986-01-29
JPH0662987B2 (ja) 1994-08-17

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