EP0394468B1 - Lubricating oil composition - Google Patents
Lubricating oil composition Download PDFInfo
- Publication number
- EP0394468B1 EP0394468B1 EP89910189A EP89910189A EP0394468B1 EP 0394468 B1 EP0394468 B1 EP 0394468B1 EP 89910189 A EP89910189 A EP 89910189A EP 89910189 A EP89910189 A EP 89910189A EP 0394468 B1 EP0394468 B1 EP 0394468B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- salt
- sulfonate
- composition
- extreme pressure
- 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 - Lifetime
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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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/08—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic sulfur-, selenium- or tellurium-containing compound
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/24—Aldehydes; Ketones
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/50—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring monocarboxylic
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/48—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring
- C10M129/54—Carboxylic acids; Salts thereof having carboxyl groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
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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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- C10M133/04—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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- C10M133/10—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms cycloaliphatic
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- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
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- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/54—Amines
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- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives thereof
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- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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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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- 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
- C10M2203/102—Aliphatic fractions
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- C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
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Definitions
- This invention relates to a novel lubricating oil composition, more particularly to a lubricating oil composition for metal working which is suitable as a processing oil for super finishing processing or bearing processing and has excellent stain resistance so that stain will not be generated not only in the absence of sulfur type extreme pressure agents but also in the presence of such agents.
- Cutting or grinding of metal is characterized in that temperature rises greatly and a fresh surface always appears upon cutting or grinding. Therefore, such an extreme pressure agent is required to have sufficient durability against the rise in temperature on friction surfaces and to react rapidly with the friction surfaces so that fresh metal surfaces which will be generated successively can be covered quickly with the lubricating film of the extreme pressure agent. For that reason, a sulfur type or chlorine type agent having high activity is generally used under very high temperature conditions.
- the sulfur type extreme pressure agent there are used, for example, sulfur simple substance, a sulfide, a sulfurized fat and oil, a sulfurized mineral oil or the like.
- a lubricating oil containing the active sulfur is excellent in processability, it has a defect that stains are generated in the processed metal product after processing and causes inevitably the lowering of the product value. Even if a lubricating oil which does not contain the aforementioned active sulfur is used, it is apprehended that stains will be generated by using a working tool (grinder) containing sulfur as an ingredient.
- a lubricating oil composition containing a base oil, a secondary amine and at least one compound selected from a sulfonate, a phenate and a salicylate.
- the substituents of said secondary amine can be alkyl, alkylaryl, aralkyl or aryl groups.
- these lubricating oil compositions still do not show a satisfying stain resistance and further possess a strong offensive odour.
- This invention has been made for the purpose of overcoming the defects in conventional lubricating oils for metal working and providing a lubricating oil composition for metal working which is excellent in stain resistance and odour so that stains will not be generated not only in the absence of a sulfur type extreme pressure agent, but also in the presence of such an agent.
- the present inventors have conducted earnest researches for developing a lubricating oil composition for metal working which is excellent in stain resistance. As a result, it has been found that the aforementioned object can be reached by incorporating a specific compound with a base oil. This invention has been accomplished on the basis of this knowledge.
- this invention provides a lubricating oil composition, characterized in that (B) an amine represented by the formula (I) and (C) at least one compound selected from the group consisting of a sulfonate, a phenate and a salicylate are incorporated into (A) a base oil and, if necessary, (D) an extreme pressure agent and/or an oiliness agent are further incorporated into the base oil.
- the base oil used as the component (A) has no limitation except that the viscosity at the temperature of 40°C is in the range of 1 to 300 cSt, and any one of the base oils which have been conventionally used in lubricating oil compositions for metal working such as a mineral oil, a synthetic oil, a sulfurized mineral oil or a sulfurized fat and oil can be used.
- a sulfur type base oil such as a sulfurized mineral oil, a sulfurized fat and oil or a sulfurized olefin advantageously gives excellent processability.
- the aforementioned base oil may be used alone or in combination of the two or more.
- the amine which is the component (B) in the composition of this invention, is the compound represented by the formula (I).
- the amine has the problems of odor or solubility.
- the aforementioned secondary amines include, for example, di(methylcyclohexyl)amine, di(ethylcyclohexyl)amine, di(propylcyclohexyl)amine, dicyclohexylamine, and the like, particularly di(methylcyclohexyl)amine and dicyclohexylamine are preferred.
- n denotes 2 to 6, preferably 3;
- R3 and R4 represent respectively a hydrogen atom or an alkyl group, an alkenyl group, a cycloalkyl group, an alkylaryl group, an aralkyl group or an aryl group having 5 to 30 carbon atoms, preferably 10 to 24 carbon atoms and may be the same or different provided that both of the two do not represent hydrogen atoms simultaneously.
- n in the above-mentioned formula (III) is less than 2, the amine has a problem of odor; and the amine in which n exceeds 6 is less available. If R3 or R4 has carbon atoms less than 5, the amine has the problems of odor or poor solubility; and the amine in which R3 or R4 has carbon atoms exceeding 30 is less available.
- the diamines include for example N-laurylpropylenediamine, N-myristylpropylenediamine, N-palmitylpropylenediamine, N-stearylpropylenediamine, N-eicosylpropylenediamine, N-oleylpropylenediamine, N,N-dilaurylpropylenediamine, tallow propylenediamine or the like.
- the amount of these amine or amines to be incorporated is generally selected in the range of 0.1 to 5% by weight, preferably 0.2 to 2% by weight on the basis of the weight of the composition. If the amount is less than 0.1% by weight, the effect of this invention cannot be exhibited satisfactorily. If the amount exceeds 5% by weight, the improvement of the effect corresponding to that amount cannot be expected.
- one or more kinds of the compounds selected from a sulfonate, a phenate and a salicylate are used as the component (C).
- the base numbers of the sulfonate, phenate and salicylate are not limited specifically and are preferably in the range of 10 to 500 mg KOH/g, more preferably 150 to 500 mg KOH/g, particularly a high base number in the range of 150 to 450 mg KOH/g being preferred.
- the component having such a high base number has good durability of the effect (particularly stain resistance).
- the sulfonate either a petroleum sulfonate or a synthetic sulfonate can be used, and as the salt form, there are mentioned an alkali metal salt, an alkaline earth metal salt, a diamine salt, an ammonium salt or the like.
- the alkaline earth metal salt particularly a calcium salt and a barium salt are preferred.
- a sulfonate which is obtained by recovering as a sulfonate a petroleum sulfonic acid which is a by-product during the purification of liquid paraffin with sulfuric acid or by sulfonating a mineral oil having a suitable molecular weight with a sulfonating agent such as concentrated sulfuric acid, fuming sulfuric acid or sulfuric acid anhydride and further converting into a sulfonate is used.
- the synthetic sulfonate there is used a sulfonate obtained by sulfonating bottoms containing as the main component didodecylbenzene as a by-product during the production of dodecylbenzene as a raw material of a synthetic detergent by alkylating, for example, benzene with a propylene tetramer, or by sulfonating dinonylnaphthalene which is obtained by the alkylation of naphthalene with nonene and further converting the sulfonic acid into a salt.
- the sulfonate having a high base number is obtained by contacting the sulfonate thus obtained with carbon dioxide gas in the presence of an excessive amount of an alkali compound such as an hydroxide, for example calcium hydroxide or barium hydroxide, or an oxide.
- an alkali compound such as an hydroxide, for example calcium hydroxide or barium hydroxide, or an oxide.
- the sulfonate may be used alone or in combination of the two or more.
- the phenate can be prepared, for example, by reacting an alkylphenol with elementary sulfur and a metal hydroxide in an alcohol as a solvent.
- an alkylphenol with elementary sulfur and a metal hydroxide in an alcohol as a solvent.
- a variety of salts in the same manner as in the sulfonate among others a calcium salt being preferred.
- the salicylate an alkali metal salt, an alkaline earth metal salt, a diamine salt or an ammonium salt of the alkylsalicylic acid represented by the general formula (II) are used: wherein R represents an alkyl group.
- alkaline earth metal salts especially the calcium salt and the magnesium salt are preferably used.
- the alkylsalicylic acid can be generally prepared by alkylating phenol with an -olefin having 14 to 18 carbon atoms and subjecting the resultant alkylphenol to Kolbe-Schmidt reaction.
- the salicylate having a high base number is prepared in the same manner as the aforementioned sulfonate.
- the alkylsalicylic acid in which the alkyl group is placed at the para-position to the hydroxyl group is advantageous because of its excellent dispersibility at high temperatures.
- the salicylate may be used alone or in combination of two or more, and it may also be combined with the aforementioned sulfonate or phenate.
- the sulfonate, the phenate or the salicylate as the component (C) is generally used in an amount of 0.1 to 10% by weight, preferably 0.2 to 5% by weight on the basis of the weight of the composition. If the amount is less than 0.1% by weight, the effect of this invention will not be exhibited satisfactorily; if it exceeds 10% by weight, the improvement of the effect corresponding to that amount cannot be expected. The optimum amount is about 1% by weight to the weight of the composition.
- an extreme pressure agent and/or an oiliness agent can be incorporated as the component (D), if necessary.
- the extreme pressure agent or the oiliness agent has no particular limitation, and those which is conventionally used in a lubricating oil for the processing of machines can be used.
- Tile extreme pressure agent reacts in a satisfactory speed with the friction surfaces under the extreme pressure condition of the loading on the friction surfaces, covers quickly the fresh metal surfaces which will generate in succession with the lubricating film, so that the extrusions on the surfaces are protected from fusion or breakage.
- a sulfur type extreme pressure agent such as sulfur as simple substance, a sulfide, a sulfurized olefin, a sulfurized mineral oil, a sulfurized fat and oil or the like
- a chlorine type extreme pressure agent such as a chlorinated paraffin, a chlorinated fat and oil, a chlorinated naphthalene, a chlorinated polyphenyl, a chlorinated alkylbenzene, methyl trichlorostearate, pentachloropentadienic acid, dibutyl chlorendate, or the like
- a phosphorus type extreme pressure agent such as tributyl phosphate, tricresyl phosphate, trioctyl phosphate, triphenyl phosphate, lauryl acid phosphate, oleyl acid phosphate, a tallow amine salt of octyl phosphate, an oleylamine salt of oleyl acid phosphate, tribut
- the oiliness agent has the effect of adsorbing on metal surfaces and forming a strong adsorption film to decrease friction.
- the oiliness agent there are mentioned, for example, a higher fatty acid such as oleic acid, stearic acid or the like; a higher alcohol such as stearyl alcohol, oleyl alcohol or the like; an amine or an ester.
- the oiliness agent may be used alone or in combination of two or more, and it may also be combined with the aforementioned extreme pressure agent.
- the extreme pressure agent or the oiliness agent as the component (D) is generally incorporated in an amount of 0.01 to 40% by weight, preferably 0.1 to 20% by weight on the basis of the weight of the composition.
- Stain resistance of the lubricating oil composition was evaluated as follows:
- the processed bearings were coated with the composition, stacked and left standing for 3 days under the conditions of 30°C and a humidity of 95%; then the stacked bearings were observed according to the following criteria:
- composition was boiled together with active sulfur in an amount of 0.5% by weight, and the composition was evaluated in the same manner as the method (1) according to the following criteria:
- sulfurized mineral oil (sulfur content: 0.5% by weight),
- Lubricating oil compositions each having a formulation shown in Table 1 were prepared, and their stain resistances were evaluated. The results are shown in Table 1.
- the extreme pressure agent and the oiliness agent were used as a mixture of the ratio 2 : 1 by weight.
- the lubricating oil composition of this invention is a lubricating oil composition for metal working which is excellent in stain resistance so that stain will not be generated not only in the absence of a sulfur type extreme pressure agent but also in the presence of such an agent.
- the lubricating oil composition of this invention is preferably used particularly for bearing processing or super finishing processing.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP229774/88 | 1988-09-16 | ||
JP22977488 | 1988-09-16 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19920115155 Division-Into EP0521534A3 (en) | 1988-09-16 | 1989-09-13 | Lubricating oil composition |
EP92115155.1 Division-Into | 1992-09-02 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0394468A1 EP0394468A1 (en) | 1990-10-31 |
EP0394468A4 EP0394468A4 (en) | 1991-03-20 |
EP0394468B1 true EP0394468B1 (en) | 1993-12-01 |
Family
ID=16897465
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP89910189A Expired - Lifetime EP0394468B1 (en) | 1988-09-16 | 1989-09-13 | Lubricating oil composition |
EP19920115155 Withdrawn EP0521534A3 (en) | 1988-09-16 | 1989-09-13 | Lubricating oil composition |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP19920115155 Withdrawn EP0521534A3 (en) | 1988-09-16 | 1989-09-13 | Lubricating oil composition |
Country Status (3)
Country | Link |
---|---|
EP (2) | EP0394468B1 (ja) |
DE (1) | DE68911129D1 (ja) |
WO (1) | WO1990002786A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7820600B2 (en) | 2005-06-03 | 2010-10-26 | Exxonmobil Research And Engineering Company | Lubricant and method for improving air release using ashless detergents |
US7851418B2 (en) | 2005-06-03 | 2010-12-14 | Exxonmobil Research And Engineering Company | Ashless detergents and formulated lubricating oil containing same |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5366648A (en) * | 1990-02-23 | 1994-11-22 | The Lubrizol Corporation | Functional fluids useful at high temperatures |
GB9524642D0 (en) * | 1995-12-01 | 1996-01-31 | Ethyl Petroleum Additives Ltd | Hydraulic fluids |
KR100519137B1 (ko) * | 1997-04-16 | 2006-01-27 | 이데미쓰 고산 가부시키가이샤 | 디젤엔진오일조성물 |
US7879775B2 (en) * | 2006-07-14 | 2011-02-01 | Afton Chemical Corporation | Lubricant compositions |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5494446A (en) * | 1978-01-10 | 1979-07-26 | Nippon Kokan Kk <Nkk> | Rust proof and lubricated steel plate |
JPS59232185A (ja) * | 1983-06-16 | 1984-12-26 | Nippon Kokan Kk <Nkk> | 冷間圧延油 |
JPS61254698A (ja) * | 1985-05-03 | 1986-11-12 | エス.シ−.ジヨンソン アンド サン,インコ−ポレ−テツド | ラノリンを含有する金属細工用流体および濃縮物と金属細工操作中における金属の潤滑および冷却法 |
JPS62100596A (ja) * | 1985-10-28 | 1987-05-11 | Daido Kagaku Kogyo Kk | 研削油剤 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
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US2798045A (en) * | 1954-09-27 | 1957-07-02 | Shell Dev | Lubricating compositions |
US2980613A (en) * | 1956-10-11 | 1961-04-18 | Sun Oil Co | Sulfur-containing lubricant inhibited against staining |
US3499839A (en) * | 1967-06-27 | 1970-03-10 | Standard Oil Co | Amine-stabilized iodine-containing lubricants |
GB1235896A (en) * | 1968-05-24 | 1971-06-16 | Mobil Oil Corp | Multifunctional fluid |
US3697426A (en) * | 1969-03-13 | 1972-10-10 | Chevron Res | Amines as antiwear additives in marine cylinder oils |
US3929650A (en) * | 1974-03-22 | 1975-12-30 | Chevron Res | Extreme pressure agent and its preparation |
JPS5943725B2 (ja) * | 1975-05-05 | 1984-10-24 | ポラロイド、コ−ポレ−シヨン | カメラの露出制御装置 |
US4161451A (en) * | 1978-03-27 | 1979-07-17 | Chevron Research Company | Lubricating oil additive composition |
CA1118750A (en) * | 1978-08-01 | 1982-02-23 | Ernst L. Neustadter | Lubricating composition |
US4505830A (en) * | 1981-09-21 | 1985-03-19 | The Lubrizol Corporation | Metal working using lubricants containing basic alkali metal salts |
EP0097118A3 (de) * | 1982-06-10 | 1984-07-25 | Ciba-Geigy Ag | Flüssige Antioxidantien für Schmierstoffe und Elastomere |
GB2149810B (en) * | 1983-11-15 | 1987-04-08 | Shell Int Research | Borated basic metal salt and oil composition containing it |
US4758363A (en) * | 1987-11-02 | 1988-07-19 | Texaco Inc. | Oxidation and corrosion resistant diesel engine lubricant |
-
1989
- 1989-09-13 DE DE89910189T patent/DE68911129D1/de not_active Expired - Lifetime
- 1989-09-13 WO PCT/JP1989/000934 patent/WO1990002786A1/ja active IP Right Grant
- 1989-09-13 EP EP89910189A patent/EP0394468B1/en not_active Expired - Lifetime
- 1989-09-13 EP EP19920115155 patent/EP0521534A3/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5494446A (en) * | 1978-01-10 | 1979-07-26 | Nippon Kokan Kk <Nkk> | Rust proof and lubricated steel plate |
JPS59232185A (ja) * | 1983-06-16 | 1984-12-26 | Nippon Kokan Kk <Nkk> | 冷間圧延油 |
JPS61254698A (ja) * | 1985-05-03 | 1986-11-12 | エス.シ−.ジヨンソン アンド サン,インコ−ポレ−テツド | ラノリンを含有する金属細工用流体および濃縮物と金属細工操作中における金属の潤滑および冷却法 |
JPS62100596A (ja) * | 1985-10-28 | 1987-05-11 | Daido Kagaku Kogyo Kk | 研削油剤 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7820600B2 (en) | 2005-06-03 | 2010-10-26 | Exxonmobil Research And Engineering Company | Lubricant and method for improving air release using ashless detergents |
US7851418B2 (en) | 2005-06-03 | 2010-12-14 | Exxonmobil Research And Engineering Company | Ashless detergents and formulated lubricating oil containing same |
Also Published As
Publication number | Publication date |
---|---|
EP0394468A1 (en) | 1990-10-31 |
EP0521534A3 (en) | 1993-02-03 |
WO1990002786A1 (en) | 1990-03-22 |
DE68911129D1 (de) | 1994-01-13 |
EP0521534A2 (en) | 1993-01-07 |
EP0394468A4 (en) | 1991-03-20 |
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