EP0155131B1 - Composition de graisse contenant un composé de bore et un savon contenant un substituant hydroxyle comme agent épaississant - Google Patents
Composition de graisse contenant un composé de bore et un savon contenant un substituant hydroxyle comme agent épaississant Download PDFInfo
- Publication number
- EP0155131B1 EP0155131B1 EP85301462A EP85301462A EP0155131B1 EP 0155131 B1 EP0155131 B1 EP 0155131B1 EP 85301462 A EP85301462 A EP 85301462A EP 85301462 A EP85301462 A EP 85301462A EP 0155131 B1 EP0155131 B1 EP 0155131B1
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- EP
- European Patent Office
- Prior art keywords
- composition according
- sulfur
- group
- grease
- phosphorus
- 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.)
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- 0 CC(*N(*)C(C)(C)*)N(*)* Chemical compound CC(*N(*)C(C)(C)*)N(*)* 0.000 description 1
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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
- C10M169/06—Mixtures of thickeners and additives
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- C10M117/00—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof
- C10M117/06—Lubricating compositions characterised by the thickener being a non-macromolecular carboxylic acid or salt thereof having more than one carboxyl group bound to an acyclic carbon atom or cycloaliphatic carbon atom
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/14—Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
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- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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- C10M2207/124—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof
- C10M2207/1245—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms containing hydroxy groups; Ethers thereof used as thickening agent
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- 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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Definitions
- the invention is concerned with the novel group of compositions. It more particularly relates to a synergistic grease composition comprising oil, hydroxy-containing soap thickener and borated amine, and optionally containing phosphorus and sulfur moieties.
- US Patents, 3125523; 3125524 and 3125525 disclose lubricating greases thickened with hydroxy fatty acid soaps and comprising salts formed from amines and borate esters.
- the present invention seeks to provide lubricating greases of improved dropping point.
- the alkyl borates include the mono-, di- and trialkyl borates, i.e., those having the methyl, ethyl, propyl, butyl, pentyl and hexyl groups.
- the amine is overborated.
- overborated is meant the presence in the borated product of more than a stoichiometric amount of boron with respect to the amine.
- the primary amines such as hexylamine, octylamine, nonylamine, decylamine, dodecylamine, tetradecylamine, octadecylamine, eicosylamine, triacontylamine, oleylamine, stearylamine, isostearylamine, tallowamine and soyamine
- the secondary amines corresponding to (1) having both groups the same or having mixtures of such groups
- the corresponding tertiary amines where again all the groups in the same molecule can be the same or different
- diamines such as N-octyl-1,2-ethylenediamine or the N-octyl-1,3-propylenediamine, N-coco-1,2-ethylenediamine or the N-coco-1,3-propylenediamine, N-oleyl-1,2-ethylenediamine
- Alkoxylated amines included are bis(2-hydroxyethyl)olelylamine, bis(2-hydroxypropyl)oleylamine, bis(2-hydroxyethyl)tallowamine, bis(2-hydroxypropyl)tallowamine, (hydroxyethyl)(hydroxypropyl)tallowamine, polyethoxylated oleylamine (containing 7 ethoxy groups) and polyethoxylated tallowamine (containing 3 ethoxy groups). Included also are hydroxyalkyl amines made by the ethoxylation or propoxylation of hydrocarbyldiamines or hydrocarbyltriamines.
- the reaction to form the condensation product (iii) can be carried out at from about 80°C to about 260°C, preferably from about 110°C to about 180°C.
- the temperature chosen will depend for the most part on the particular reactants and on whether or not a solvent is used.
- Reaction pressures can be vacuum, atmospheric or positive pressure.
- quantities of reactants be chosen such that the molar ratio of amine to boric acid be from about 0.2 to about 2, preferably from about 0.5 to about 0.9.
- the amine can be reacted with an excess of the boric acid to form a condensation product containing from about 0.1% by weight of boron to as much as 10% or more of boron.
- reaction can be advantageously run at from about 1 to about 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 solvents which include propanol, butanol, hexamethylene glycol and the like, can be used. Mixtures of alcoholic and hydrocarbon solvents can also be used.
- any phase of the process can be carried out from about 1 to about 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 metal, alkaline earth metal or amine soaps of hydroxy-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 and esters containing 12-hydroxystearates, 14-hydroxystearic acid, 16-hydroxystearic acid and 6-hydroxystearic acid.
- 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, i.e., 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 metals soaps of methyl-12-hydroxystearate, diesters of a C 4 to C 12 dicarboxylic acid and tall oil or marine 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 carpylate-acetate (U.S. Patent No. 2,999,066) and calcium salts and soaps of low-, intermediate- and high-mblecular weight acids 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-caprylate-acetate complexes (U.S. Patent No. 2,999,065), calcium carpylate-acetate (U.S. Patent No. 2,999,066) and calcium salts and soap
- thickening agents comprises substituted ureas, phthalocyamines, indanthrene, pigments such as perylamides, 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, and does not form a part of the present invention.
- Manufacture of the thickening agents can be done in a variety of grease making equipment such as in open kettles at reduced, atmospheric, or positive pressures; in higher pressure reaction chambers which may be operated to as high as 180 psig; or in continuous manufacturing equipment.
- the temperature range from the bulk grease under manufacture can range from 15°C (60°F) to 238°C (460°F).
- the third member(s) that may be present in the grease composition are the phosphorus and sulfur moities. Both of these can be present in the same molecule, such as in a metal or non-metal phosphorodithioate of the formula wherein R 6 is a hydrocarbyl group containing 3 to 18 carbon atoms, M is a metal or non-metal, n is the valence of M and Z is oxygen or sulfur, at least one Z being sulfur.
- R 6 is preferably an alkyl group and may be a propyl, butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl or octadecyl group, including those derived from propanol, 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, molybdenum, 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, epoxides such as propylene oxide and 1,2-epoxydodecane and amine salts. They also include other nitrogenous compounds such as those derived from hydrocarbyl amines and diamines, including oleylamine and N-oleyl-1,3-propylenediamine and such as the imidazolines and oxazolines.
- 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 sulfide, sulfurized terpenes, phosphorodithionyl disulfide and sulfurized jojoba oil.
- the phosphites embrace the dibutyl, dihexyl, dioctyl, didecyl and similar phosphites.
- 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.
- 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 about 45 SSU at 100°F to about 6000 SSU at 100°F, and preferably from about 50 to about 250 SSU at 210°F.
- These oils may have viscosity indexes ranging up to about 100 or higher. Viscosity indexes from about 70 to about 95 are preferred.
- the average molecular weights of these oils may range from about 250 to about 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, este'f's of phosphorus-containing acids, liquid ureas, ferrocene derivatives, hydrogenated synthetic oils, chain-type polyphenyls, siloxanes and silicones (polysiloxanes), alkyl-substituted diphenyl esters typified by a butyl-substituted bis(p-phenoxy phenyl) ether, phenoxy phenylethers
- the metallic soap grease compositions containing one or more of the borated amines, and optionally, one or more of the sulfur and phosphorus combinations described herein provide advantages in increased dropping point, improved grease consistency properties, antirust characteristics and potential antifatigue, antiwear and antioxidant benefits unavailable in prior greases.
- the grease of this invention is unique in that it can be preferably manufactured by the admixture of additive quantities of the alcohol borates to the fully formed soap grease after completion of saponification.
- N-tallow-1,3-propylenediamine obtained as Duomeen T obtained from Armak Chemical Co.
- boric acid as generally described in Example 1.
- the borated N-tallow-1,3-propylenediamine was blended with an equal wt. of 100 second process oil to form a 50% concentrate in mineral oil.
- a lithium hydroxystearate grease thickener was prepared by saponification of a mixture containing 12-hydroxystearic acid (8%) and the glyceride thereof (9%) with lithium hydroxide in a mineral oil vehicle at about 177°C in a closed contactor.
- Example 4 To the base grease of Example 4, was added at about 115°C, 1.0 wt.% of the borated N-tallow-1,3-propylenediamine of Example 2.
- Example 4 50 wt.% of the base grease used in Example 4 plus 50 wt.% of the grease of Example 9, producing a 50-50 mixture of hydroxy- and non-hydroxy-containing thickeners.
- Examples 7 and 8 show a significant effect upon hydroxy-containing carboxylate soap thickened grease when the borated amines described are used.
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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)
Claims (25)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT85301462T ATE55406T1 (de) | 1984-03-07 | 1985-03-05 | Eine borverbindung und eine hydroxy-substituierte seife als verdickungsmittel enthaltende fettzusammensetzung. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US58732884A | 1984-03-07 | 1984-03-07 | |
US64107784A | 1984-08-15 | 1984-08-15 | |
US641077 | 1984-08-15 | ||
US587328 | 1984-08-15 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0155131A2 EP0155131A2 (fr) | 1985-09-18 |
EP0155131A3 EP0155131A3 (en) | 1986-04-23 |
EP0155131B1 true EP0155131B1 (fr) | 1990-08-08 |
Family
ID=27079982
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85301462A Expired - Lifetime EP0155131B1 (fr) | 1984-03-07 | 1985-03-05 | Composition de graisse contenant un composé de bore et un savon contenant un substituant hydroxyle comme agent épaississant |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0155131B1 (fr) |
JP (1) | JPH0635590B2 (fr) |
AU (1) | AU578070B2 (fr) |
BR (1) | BR8501026A (fr) |
CA (1) | CA1280738C (fr) |
DE (1) | DE3579015D1 (fr) |
NZ (1) | NZ211296A (fr) |
PH (1) | PH22814A (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0157969B2 (fr) * | 1984-04-05 | 2000-01-12 | The Lubrizol Corporation | Compositions organo-borate et leurs utilisations dans des lubrifiants |
JPS6346299A (ja) * | 1986-01-16 | 1988-02-27 | Ntn Toyo Bearing Co Ltd | プランジング型等速ジョイント用グリース |
US4822505A (en) * | 1987-07-31 | 1989-04-18 | Exxon Research And Engineering Company | Load-carrying grease |
CN106661493B (zh) | 2015-02-09 | 2020-11-13 | 株式会社Moresco | 润滑剂组合物及其利用、以及脂肪族醚化合物 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3125524A (en) * | 1964-03-17 | Lubricating greases containing salts of | ||
US3125523A (en) * | 1964-03-17 | Lubricating greases containing salts of | ||
US3125525A (en) * | 1964-03-17 | Lubricating greases containing borate | ||
BE780687A (fr) * | 1972-03-15 | 1972-07-03 | Labofina Sa | Graisses lubrifiantes. |
US3940339A (en) * | 1975-01-21 | 1976-02-24 | Exxon Research & Engineering Co. | Lithium borate complex grease exhibiting salt water corrosion resistance |
CA1097319A (fr) * | 1977-03-14 | 1981-03-10 | John H. Adams | Graisse contenant des borates comme additifs extreme- pression |
US4382006A (en) * | 1979-11-06 | 1983-05-03 | Mobil Oil Corporation | Friction reduction additives and compositions thereof |
US4328113A (en) * | 1980-01-14 | 1982-05-04 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
AU549639B2 (en) * | 1981-07-01 | 1986-02-06 | Chevron Research Company | Lubricating oil composition to improve fuel economy |
GB2106133B (en) * | 1981-09-22 | 1985-01-09 | Chevron Res | Method of reducing brake chatter of oil immersed disc brakes |
JPS58125794A (ja) * | 1982-01-21 | 1983-07-26 | Showa Shell Sekiyu Kk | 音響特性が改善された高滴点リチウムコンプレツクスグリ−ス組成物 |
JPS5925891A (ja) * | 1982-08-03 | 1984-02-09 | Karonaito Kagaku Kk | 潤滑油組成物 |
-
1985
- 1985-02-26 CA CA000475128A patent/CA1280738C/fr not_active Expired - Lifetime
- 1985-03-04 NZ NZ211296A patent/NZ211296A/xx unknown
- 1985-03-05 DE DE8585301462T patent/DE3579015D1/de not_active Expired - Fee Related
- 1985-03-05 EP EP85301462A patent/EP0155131B1/fr not_active Expired - Lifetime
- 1985-03-05 AU AU39525/85A patent/AU578070B2/en not_active Ceased
- 1985-03-05 PH PH31944A patent/PH22814A/en unknown
- 1985-03-07 BR BR8501026A patent/BR8501026A/pt not_active IP Right Cessation
- 1985-03-07 JP JP60045696A patent/JPH0635590B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
PH22814A (en) | 1988-12-27 |
BR8501026A (pt) | 1985-10-29 |
DE3579015D1 (de) | 1990-09-13 |
EP0155131A2 (fr) | 1985-09-18 |
EP0155131A3 (en) | 1986-04-23 |
NZ211296A (en) | 1988-07-28 |
CA1280738C (fr) | 1991-02-26 |
AU578070B2 (en) | 1988-10-13 |
AU3952585A (en) | 1985-09-12 |
JPS60217298A (ja) | 1985-10-30 |
JPH0635590B2 (ja) | 1994-05-11 |
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