US3280029A - Lubricant compositions - Google Patents

Lubricant compositions Download PDF

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Publication number
US3280029A
US3280029A US376249A US37624964A US3280029A US 3280029 A US3280029 A US 3280029A US 376249 A US376249 A US 376249A US 37624964 A US37624964 A US 37624964A US 3280029 A US3280029 A US 3280029A
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test
oil
water
vapor phase
emulsions
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US376249A
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Hans F Waldmann
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ExxonMobil Oil Corp
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Mobil Oil Corp
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Priority to US376249A priority Critical patent/US3280029A/en
Priority to FR20703A priority patent/FR1496057A/fr
Priority to GB25446/65A priority patent/GB1083293A/en
Priority to NL6507854A priority patent/NL6507854A/xx
Priority to DES97661A priority patent/DE1282829B/de
Priority to AT550665A priority patent/AT276604B/de
Priority to BE665657A priority patent/BE665657A/xx
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M173/00Lubricating compositions containing more than 10% water
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02Water
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    • C10M2203/00Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108Residual fractions, e.g. bright stocks
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
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    • C10M2205/00Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/021Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/022Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/281Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/282Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/283Esters of polyhydroxy compounds
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/286Esters of polymerised unsaturated acids
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/287Partial esters
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28Esters
    • C10M2207/34Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
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    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
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    • C10M2215/26Amines
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
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    • C10M2227/00Organic 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
    • C10M2227/02Esters of silicic acids
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    • C10M2229/00Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
    • C10M2229/02Unspecified siloxanes; Silicones
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    • C10M2229/04Siloxanes with specific structure
    • C10M2229/05Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/08Resistance to extreme temperature
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    • C10N2030/00Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/12Gas-turbines
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    • C10N2040/12Gas-turbines
    • C10N2040/13Aircraft turbines
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    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/135Steam engines or turbines
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    • C10N2040/20Metal working
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    • C10N2050/00Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01Emulsions, colloids, or micelles

Definitions

  • the present invention is directed to lubricant compositions possessing improved characteristics. More particularly, it is directed to improved lubricating oils and waterin-oil emulsions.
  • vapor phase corrosion or rusting of metal parts is often an acute problem in machines or systems which contain water. Such corrosion most frequently occurs at the metal surfaces enclosing vapor spaces, and is a particular problem in systems which employ water-in-oil emulsions such as hydraulic fluids as functional fluids for transmitting mechanical energy. Indeed, .although water-in-oil emulsions are widely used today as lubricants and functional fluids, this problem of vapor phase corrosion is a major drawback to their more widespread use particularly as functional fluids for power transmission and the like.
  • compositions which are capable of imparting effective and longlasting vapor phase corrosion resistance, improved antifatigue qualities and other desirable characteristics.
  • a further object is to provide a method for improving the characteristics of such lubricants.
  • Another object is a method for enhancing the vapor phase corrosion resistance and anti-fatigue characteristics of metals which are subject to conditions which promote vapor phase corrosion and metal fatigue.
  • a further object is to provide effective additives for 1u bricants.
  • a particular object of the present invention is to provide water-in-oil emulsions exhibiting superior characteristics especially vapor phase corrosion resistance and anti-fatigue characteristics.
  • R represents an alkyl group
  • R represents an alkyl group the same or different from R, or a hydrogen atom
  • R and R are selected so that 3,280,029 Patented Oct. 18, 1966 "ice sum of the groups represented by R-l-R does not exceed 10 carbon atoms;
  • X is an alkylene group having from 2 to about 4 carbon atoms
  • n 1 or 2.
  • alkyl groups present in these amine compounds may be either straight or branched-chain; primary, secondary or tertiary alkyls so long as the combined total of carbon atoms does not exceed ten.
  • the alkylen groups represented by X may be straight or branched-chain and can be derived from either primary, secondary or tertiary alkyls.
  • the compounds encompassed thereby may be characterized as monoalkyl or dialkyl amino mono-alkanols or alkoxy mono-alkanols.
  • Some examples of such compounds include: monomethyl amino ethanol, dimethyl amino ethanol, monoethyl amino ethanol, monoethyl amino ethoxy ethanol, diethyl amino ethanol, diethyl amino ethoxy ethanol, diisopropyl amino ethanol, dibutyl amino ethanol, dibutyl amino ethoxy ethanol, n-butyl amino ethanol, dimethylamino-2-propanol, diisopropyl amino 2- propanol, n-butyl amino 2-propanol, isobutyl amino 2- propanol, dimethyl amino Z-butanol, dimethyl amino 1- butanol, etc.
  • alkyl amino mono-alkanol compounds described herein may be advantageously employed in a variety of liquid lubricant compositions. They are particularly effective in liquid lubricant compositions which contain water as a component or impurity, or in liquid lubricants employed in machines, apparatus or systems which are subject to conditions which promote vapor phase corrosion and/or metal fatigue either in the presence or absence of water.
  • liquid lubricants include mineral oil or synthetic oil-based lubricating oil compositions suitable for use as automotive lubricants such as motor oils, gear oils and the like; aviation lubricants including jet engine oils; marine lubricants such as marine diesel oils; industrial lubes as exemplified by metal working oils, gear oils; and the like. Also included are the single phase lubricating compositions or functional fluids containing water and a synthetic base oil such as the glycol fluids containing water, glycols and polyglycols.
  • waterin-oil emulsions such as those employed as metal working fluids, oven chain lubricants, as well as those used as functional fluids such as hydraulic fluids, transmission fluids etc.
  • the use of the aforedescribed monoalkanol compounds with water-in-oil emulsions is a particular aspect of the present invention. It has been found that the instant mono-alkanol compounds because of their alkaline character are compatible with and particularly effective in water-in-oil emulsions which possess an alkaline or in some cases neutral environment. This is in contrast to behavior of heretofore known acidic inhibitors which tend to precipitate out of the alkaline emulsions. By employing the instant alkyl amino mono-alkanols
  • liquid lubricants both lubricating oils and water-in-oil emulsions
  • base oils include mineral oils from different crudes, i.e., naphthenic, paraflinic, etc.; which have ben solvent and acid refined, hydrocracked etc.; and synthetic oils such as olefin polymers, hydrogenated olefin polymers, alkylene oxide polymers,
  • dicarboxylic acid esters liquid esters of phosphorus, monomeric and polymeric silicones, esters of polyhydroxy alcohols and the like.
  • the base oil and water may be employed in various relative proportions, the water being present generally in the range from about to 70% by weight of the emulsion.
  • Water-in-oil emulsions containing hydrocarbon base oils of from about 50- 400 S.U.V. at 100 F. are of particular interest.
  • alkyl amino mono-alkanol compounds defined hereinabove is necessary in order to achieve the desired vapor phase rust resistance, antifatigue properties and other desirable characteristics.
  • the structure and characteristics of these specific mon0- alkanol compounds is important for it has been found, as will be shown hereinafter, that similar compounds including alkyl amines and certain di-alkanol compounds are not as effective in lubricant compositions.
  • the instant alkyl amino mono-alkanols must be present in the lubricant in an effective state.
  • the mono-alk-anol compound should be free to act in the lubricant composition. This invention therefore should be distinguished from the use of reaction products, complexes or the like of the mono-alkanol compounds with other components wherein the mono-alkanols would be tied up or otherwise have their effectiveness diminished or destroyed.
  • Vapor phase anti-rust test This test measures the eflectivenes of various amino compounds as vapor phase rust inhibitors in lubricants. According to the test procedure, a 16 ounce tallform widemouth glass jar is half filled with the fluid to be tested. A sandblasted and solvent-cleaned steel test panel is attached to the inside of a tin lid with a magnet and the lid then screwed loosely onto the glass jar to allow some breathing. The jar is then immersed overnight up to the fluid level in a water bath maintained at 175 F. and during the day removed and stored at room temperature for 8 hours. The vapor phase anti-rust capability of the fluid is determined by measuring the percent of test panel surface rusted after various periods of exposure. The smaller percent of rusting the more eifective is the inhibitor.
  • the isopropyl amino ethanol employed in the following tests is, unless otherwise indicated, a commercial product containing about 60% of isopropyl amino ethanol.
  • Vapor phase anti-rust tests were conducted for more extended periods of time (up to days) on several types of water-in-oil emulsions and lubricating oils as reported in Table 4.
  • water was added to each of the lubricating oil compositions and to the premium hydraulic fluid in the amounts shown in the table.
  • the test procedure employed described above was used but the jar was immersed in a water bath maintained at 180 F. instead of at F.
  • the Vickers pump test which is a recognized test for 5 Commercial hydraulic oil containing 150 S.U.S. (100 F.) solventrefined neutral paraifinie mineral oil and about 40% water.
  • Oil blend consisting of 64% paraflinic solvent-refined neutral mineral oil of 200 S.U.S. (100 F.) and 36% bright stock of 2,650 S.U.S. (100 F.).
  • the failure was de- Zgg $8 23 25 tected by an overload device when the amperage exceeded 605 70 34s a preset level.
  • the results are given in the following 4 do 0 07 g 8% Table 7 where it is seen that the addition of the iso- 340 2 20 164 propylamino ethanol lengthened the time period to failure 980 100 200 5 lsoprppylamme plus hewb Q1 g from 165 hours (test 1) to 279 hours (test 2).
  • alkyl amino mono-alkanol compounds of the invention may be employed in the form of relatively pure compounds or as mixtures of dilferent alkyl amino monoalkanols.
  • the amount of alkyl alkanol amines which should be used in the lubricant compositions will vary depending on such factors as the nature of the lubricant, its intended use, the presence or absence of other additives, etc. In general, from about 0.05 to about 5 weight percent, preferably from about 0.1 to about 1.0 weight percent are suitable. The use of larger amounts may in some instances be suitable depending on economic considerations.
  • the lubricant compositions of the invention may also contain other ingredients normally used with such compositions such as antioxidants, detergents, V.I. improvcrs, inhibitors, E.P. agents, pour point improvers, and in the case of water-in-oil emulsions, emulsifiers, stabilizing agents, anti-freeze agents etc.
  • R represents an alkyl group
  • R is selected from the class consisting of alkyl groups and hydrogen atoms
  • R+R' is equal to from 1 to about 10 carbon atoms
  • X is an alkylene group having from 2 to about 4 carbon atoms
  • n represents an integer selected from the class consisting of l and 2.
  • composition of claim 1 which contains a lubricating oil.
  • composition of claim 4 wherein said vapor phase anti-corrosion agent is butylamino ethanol.
  • composition of claim 4 wherein said vapor phase anti-corrosion agent is dimethylamino ethanol.
  • composition of claim 1 which contains a water- 5 18.
  • a liquid lubricating composition containing a minor fatigue wherein the said metal surfaces enclose vapor amount of a vapor phase anti-corrosion agent of the forspaces in which water is present which comprises the steps mula: of (1) incorporating into a liquid lubricating composition R an effective amount suflicient to provide vapor phase corrosion resistance and anti-fatigue characteristics thereto NAXTOMH of a compound of the formula R R where R represents an alkyl group; R is selected from N(X O)H the class consisting of alkyl groups and hydrogen atoms; the 511m of -iis equal to from 1 to about 10 Carbon where R represents an alkyl group: R is selected from atoms; X is an alkylene group having from 2 to about the class consisting of alkyl groups and hydrogen atoms; 4 carbon atoms; and n represents an
  • the composition of claim 4 which contains water. 4 carbon atoms; and n represents an integer selected from 6.
  • the composition of claim 4 which contains a mineral the class consisting of 1 and 2, and (2) introducing said lubricating oil. liquid lubricating composition into a moving lubrication 7.
  • the composition of claim 4 which contains a synsystem operating under conditions normally conductive to thetic lubricating oil. the formation of water vapor whereby the said moving 8.
  • the composition of claim 4 which contains a watermetal surfaces are contacted therewith. in-oil emulsion. 19. The process of claim 18 wherein the said com- 9.
  • composition of claim 8 wherein said water-in-oil pound is isopropylamino ethanol. emulsion contains from about 10 to about 70% by weight 20.
  • the process of claim 18 wherein said additive is of water. employed in an amount from about 0.05 to about 5 weight 10.
  • the composition of claim 4 wherein said vapor percent. phase anti-corrosion agent is present in an amount from 21.
  • said liquid lubabout 0.05 to about 5 weight percent. ricating composition is a water-in-oil emulsion.
  • composition of claim 4 wherein said vapor phase anti-corrosion agent is isopropylamino ethanol.
  • References Cited y the Examiner 12 The composition of claim 4 wherein said vapor UNITED STATES PATENTS i? 95 2 855 .agent diethylammc p 2 512,949 1950 Li 252 39z X position of clalm 4 wherem said vapor 2 56 88 10/1960 D 252 3 X phase anti-corrosion agent is diisopropylamino ethanol.
  • 9 enman 92 14 A hydraulic fluid containing from about 10 to about by weight of water, a hydrocarbon oil having OTHER REFERENCES a Saybolt Universal viscosity at F.

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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)
US376249A 1964-06-18 1964-06-18 Lubricant compositions Expired - Lifetime US3280029A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
US376249A US3280029A (en) 1964-06-18 1964-06-18 Lubricant compositions
FR20703A FR1496057A (fr) 1964-06-18 1965-06-14 Nouvelles compositions lubrifiantes
GB25446/65A GB1083293A (en) 1964-06-18 1965-06-16 Lubricant composition
NL6507854A NL6507854A (de) 1964-06-18 1965-06-18
DES97661A DE1282829B (de) 1964-06-18 1965-06-18 Waessrige Schmieroelmischungen
AT550665A AT276604B (de) 1964-06-18 1965-06-18 Flüssige Schmiermittelzusammensetzungen
BE665657A BE665657A (de) 1964-06-18 1965-06-18

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US3280029A true US3280029A (en) 1966-10-18

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US (1) US3280029A (de)
AT (1) AT276604B (de)
BE (1) BE665657A (de)
DE (1) DE1282829B (de)
FR (1) FR1496057A (de)
GB (1) GB1083293A (de)
NL (1) NL6507854A (de)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3859221A (en) * 1973-04-20 1975-01-07 Mobil Oil Corp Lubricant compositions exhibiting synergistic relief of metal fatigue
US4483777A (en) * 1982-09-20 1984-11-20 Mobil Oil Corporation Stability improvers for water-in-oil emulsion
US4670172A (en) * 1985-03-29 1987-06-02 Borg-Warner Corporation Process and kit for working metals
US4738797A (en) * 1985-12-20 1988-04-19 Borg-Warner Chemicals, Inc. Aminocarboxylic acid-terminated polyoxyalkylene containing extreme pressure functional compositions
US4749503A (en) * 1986-03-07 1988-06-07 Chemical Exchange Industries, Inc. Method and composition to control microbial growth in metalworking fluids
US4760176A (en) * 1985-12-20 1988-07-26 Borg-Warner Chemicals, Inc. Aminocarboxylic acid-terminated polyoxy-alkylenes and process for the preparation thereof
US4795583A (en) * 1987-12-28 1989-01-03 Ethyl Petroleum Additives, Inc. Shift-feel durability enhancement
US4976919A (en) * 1984-10-30 1990-12-11 Berol Kemi Ab Method for mechanically working cobalt-containing metal
US5135668A (en) * 1990-02-09 1992-08-04 Scandinavian Oilfield Chemicals A/S Process for inhibiting corrosion in oil production fluids
WO1994013765A1 (en) * 1992-12-17 1994-06-23 Berol Nobel Ab Use of a secondary amine as a corrosion inhibiting and antimicrobial agent and an aqueous alkaline industrial fluid containing said amine
US5549838A (en) * 1994-03-25 1996-08-27 Nippon Oil Co., Ltd. Hydraulic working oil composition for buffers
US5773393A (en) * 1991-09-16 1998-06-30 The Lubrizol Corporation Oil compositions useful in hydraulic fluids
WO2021198478A1 (en) * 2020-04-03 2021-10-07 Shell Internationale Research Maatschappij B.V. Water-glycol hydraulic fluid composition and supplementary additive therefor
EP4105303A1 (de) * 2021-06-16 2022-12-21 Rhodia Operations Additive aus saps-freie twin-tail-amin-derivaten für schmiermittel zur reibungsmodifizierung und zum verschleissschutz

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2512949A (en) * 1945-12-22 1950-06-27 Nox Rust Chemical Corp Corrosion inhibitor for metals
US2956889A (en) * 1956-02-06 1960-10-18 Dearborn Chemicals Co Corrosion inhibition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2512949A (en) * 1945-12-22 1950-06-27 Nox Rust Chemical Corp Corrosion inhibitor for metals
US2956889A (en) * 1956-02-06 1960-10-18 Dearborn Chemicals Co Corrosion inhibition

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3859221A (en) * 1973-04-20 1975-01-07 Mobil Oil Corp Lubricant compositions exhibiting synergistic relief of metal fatigue
US4483777A (en) * 1982-09-20 1984-11-20 Mobil Oil Corporation Stability improvers for water-in-oil emulsion
US4976919A (en) * 1984-10-30 1990-12-11 Berol Kemi Ab Method for mechanically working cobalt-containing metal
US4670172A (en) * 1985-03-29 1987-06-02 Borg-Warner Corporation Process and kit for working metals
US4738797A (en) * 1985-12-20 1988-04-19 Borg-Warner Chemicals, Inc. Aminocarboxylic acid-terminated polyoxyalkylene containing extreme pressure functional compositions
US4760176A (en) * 1985-12-20 1988-07-26 Borg-Warner Chemicals, Inc. Aminocarboxylic acid-terminated polyoxy-alkylenes and process for the preparation thereof
US4749503A (en) * 1986-03-07 1988-06-07 Chemical Exchange Industries, Inc. Method and composition to control microbial growth in metalworking fluids
US4795583A (en) * 1987-12-28 1989-01-03 Ethyl Petroleum Additives, Inc. Shift-feel durability enhancement
US5135668A (en) * 1990-02-09 1992-08-04 Scandinavian Oilfield Chemicals A/S Process for inhibiting corrosion in oil production fluids
US5773393A (en) * 1991-09-16 1998-06-30 The Lubrizol Corporation Oil compositions useful in hydraulic fluids
WO1994013765A1 (en) * 1992-12-17 1994-06-23 Berol Nobel Ab Use of a secondary amine as a corrosion inhibiting and antimicrobial agent and an aqueous alkaline industrial fluid containing said amine
US5633222A (en) * 1992-12-17 1997-05-27 Berol Nobel Ab Use of a secondary amine as a corrosion inhibiting and antimicrobial agent and an aqueous alkaline industrial fluid containing said amine
US5549838A (en) * 1994-03-25 1996-08-27 Nippon Oil Co., Ltd. Hydraulic working oil composition for buffers
WO2021198478A1 (en) * 2020-04-03 2021-10-07 Shell Internationale Research Maatschappij B.V. Water-glycol hydraulic fluid composition and supplementary additive therefor
CN115397959A (zh) * 2020-04-03 2022-11-25 国际壳牌研究有限公司 水-二醇液压流体组合物及其辅助添加剂
EP4105303A1 (de) * 2021-06-16 2022-12-21 Rhodia Operations Additive aus saps-freie twin-tail-amin-derivaten für schmiermittel zur reibungsmodifizierung und zum verschleissschutz
WO2022263462A1 (en) * 2021-06-16 2022-12-22 Rhodia Operations Saps-free twin-tail amine derivatives additives for lubricant for friction modification and wear prevention

Also Published As

Publication number Publication date
GB1083293A (en) 1967-09-13
BE665657A (de) 1965-12-20
AT276604B (de) 1969-11-25
FR1496057A (fr) 1967-09-29
NL6507854A (de) 1965-12-20
DE1282829B (de) 1968-11-14

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