US3367868A - Rust inhibited poly(hexafluoropropylene oxide) oil compositions - Google Patents

Rust inhibited poly(hexafluoropropylene oxide) oil compositions Download PDF

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US3367868A
US3367868A US53931466A US3367868A US 3367868 A US3367868 A US 3367868A US 53931466 A US53931466 A US 53931466A US 3367868 A US3367868 A US 3367868A
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cf
oil
oxide
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hexafluoropropylene
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Skehan John Tevlin
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E I du Pont de Nemours and Co
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00Ethers; Compounds having groups, groups or groups
    • C07C43/02Ethers
    • C07C43/03Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04Saturated ethers
    • C07C43/12Saturated ethers containing halogen
    • C07C43/126Saturated ethers containing halogen having more than one ether bond
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M3/00Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23FNON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/12Oxygen-containing compounds
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/044Acids; Salts or esters thereof
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06Perfluorinated compounds
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/04Organic macromolecular compounds containing halogen as ingredients in lubricant compositions obtained from monomers containing carbon, hydrogen, halogen and oxygen
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2213/00Organic macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2213/06Perfluoro polymers
    • CCHEMISTRY; METALLURGY
    • 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
    • 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
    • CCHEMISTRY; METALLURGY
    • 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
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26Amines

Description

United States Patent Ofifice 3,367,868 Patented Feb. 6, 1968 3,367,868 RUST INHIBITED POLY(HEXAFLUOROPRO- PYLENE OXIDE) 01L COMPDSHTIONS John Tevlin Skehan, Claymont, DeL, assignor to E. I. du Pont de Nemours and Company, Wilmington, Del., a corporation of Delaware No Drawing. Filed Apr. 1, 1966, Ser. No. 539,314 9 Claims. (Cl. 252-34.7)

R OfCF CF CF Ol cF CF and motor CF CF oi CF CF 3 CF (CF *EOCF CF (CFa ErrOR in which R, is a perfiuoroalkyl group having 1 to about 6 carbon atoms. These oils may be tailored, if desired, to operate at temperatures as high as 800 F. They are not affected by either oxygen or moisture at these temperatures. However, rusting of ferrous metals has been encountered at these temperatures. Accordingly, it is desirable to provide inhibitors which prevent rusting of these metals at extreme temperatures.

These oils are also used to prevent rusting of metal parts at ambient temperatures. Many parts or subassemblies of devices, after being manufactured, are filled with these oils and stored until needed, often a considerable period of time. Although poly(hexafluoropropylene oxide) oils are superior to hydrocarbon oils for this use, complete rust prevention is not obtained with these oils alone.

In order to be useful with these oils, a rust inhibitor must possess a number of specific properties. First of all, it must inhibit rust. Furthermore, it must be soluble in and compatible with the oil. The solubility must be sufiicient to provide an effective amount of inhibitor in the oil, both at operating temperatures and at ambient temperatures. There must be no separation of the inhibitor from the oil even while the device containing the oil is not in use. The inhibitor itself must also possess a high degree of thermal stability at the temperatures at which the oils are used. Aninhibitor which decomposes under operating conditions will lose its effectiveness rapidly. Moreover, the inhibitor should not seriously affect lubricant properties, particularly lubricity, oil viscosity and oil viscosity index. These and other requirements eliminate most, if not all, known rust inhibitors.

It is an object of this invention to provide poly(hexafluoropropylene oxide) oil compositions containing rust inhibitors which considerably reduce or prevent rusting of ferrous metals even at extremely high temperatures. Other objects will become apparent from the following description of this invention.

It has now been discovered that reduced rusting of ferrous metals in the presence of poly(hexafiuoropropylene oxide) oils can be obtained by using a poly(hexafiuoropropylene oxide) oil composition which comprises poly(hexafluoropropylene oxide) oil of the structure R OfCF CF 3 CF 0) i CF CF or R OfCF (SP CF Oi CF CF CF (CF 3 )-EOCF CF (CF 3 550R;

where n, p and r are integers indicating the degree of polymerization and R is a perfiuoroalkyl group having 1 to about 6 carbon atoms, said oil having an average molecular weight of at least about 3,000 and a pour point not in excess of about 50 F. and, as rust inhibitor, an effective amount of perfluoroalkylether acid or corre sponding ammonium salt of the structure R O-ECF (CF CF oi CF (CF 3 )1 COOB in which m is about 7 to 18, B is H or NH, and Rf is as previously stated.

Poly(hexafluoropropylene oxide) oils of the above structures are extremely stable at elevated temperatures. Those polymers having average molecular weights of at least about 3,000 and pour points not in excess of about 50 F. are quite useful as lubricating oils. Polymers of the type R O ECF (CF CF Oi CF CF having an average molecular weight of about 5,500 to 7,000 are preferred. These molecular weight designations are based upon number average molecular weights obtained by the spectroscopic method. The pour point designation is based upon Federal Test Method Standard 791, method 351.

These poly(hexafluoropropylene oxide) oils may be prepared in several ways. Hexafluoropropylene oxide is readily homopolymerized to products of the structure cF cF CF OfCF (CE, CF O} CF CF, COF where n is 0 or an integer indicating the degree of polymerization, as described in Canadian Patent No. 725,740, issued Jan. 11, 1966. Polymers of the structure where x and y are each 1 to about 4, are prepared by polymerizing hexafluoropropylene oxide in the presence of a ketone of the structure as described in Canadian Patent No. 707,363, issued Apr. 6, 1965. Polymers of the structure F (CF CF O-fCF CF CF Oii CF (CF COF where z is 0 to about 5 are prepared by polymerizing hexafluoropropylene oxide in the presence of an acid fluoride of the formula F (CF COF RfO'ECF (CF CF OPr CF (CF COOH where R, is a perfiuoroalkyl group having 1 to about 6 carbon atoms. The acids derived from these products react with elemental fluorine according to the method of British Patent No. 1,000,802 to form These polymers also dimerize under the influence of ultraviolet light, as described in U.S. Patent No. 3,214,- 478, to form oils of the formula The rust inhibitors used in the compositions of this invention are the perfluoroalkyl ether carboxylic acids and corresponding ammonium salts of the structure in which m is about 7 to 18, B is H or NH, and R is a perfiuoroalkyl group having 1 to about 6 carbon atoms. Preferably m is about 7 to 10 and R is CF CF CF These acids are prepared by hydrolyzing hexafluoro propylene oxide polymers of the structure RHECF CF CF Oi CF (CF 3 COP as indicated above. The corresponding ammonium salts are prepared by first mixing the acid with a suitable solvent, such as toluene in which the acid partially dissolves and partially disperses in finely divided form. Ammonia gas is then bubbled through the mixture at room temperature. After all of the acid has been neutralized, the solvent is evaporated under vacuum leaving the solid ammonium salt of the acid.

The poly(hexafluoropropylene oxide) oil composition of this invention should contain an effective amount of the acid or ammonium salt as rust inhibitor. By eflective amount is meant the amount required to produce a useful inhibitor effect for the required service life of the device containing the oil at the operating temperature. The various ferrous metals differ considerably in the amount of rust which will occur and the amount of inhibitor required to prevent it. Furthermore, inhibitor is probably consumed while doing its job, hence increased service life or higher use temperatures will require larger amounts of inhibitor. Accordingly, the exact amount of inhibitor required for specific applications will vary considerably.

In general, the amount of acid or ammonium salt in the oil composition will be in the range of about 0.1 to 2% by weight. So long as at least about 0.1% of inhibitor is present, a significant amount of rust inhibition is obtained. As the amount of inhibitor is increased, a quantitative reduction in rusting is obtained up to a point. More than about 2% of inhibitor seldom produces any significant increase in effect. To prevent rusting over long periods, it is preferable to add about 1 to 2% of the acid or ammonium salt. These rust inhibitors are completely soluble in the poly(hexafluoropropylene oxide) oils in the required amounts.

The following examples, illustrating the novel oil compositions of this invention and their utility, are given without any intention that the invention be limited thereto. All percentages are by weight.

Examples 1 and 2 Oil compositions containing poly(hexafluoropropylene oxide) of the formula having an average molecular weight of 4,300 and 0.2% of an acid or ammonium salt of the structure n-C F O-ECF (CF CF OhCF (C1 COOB in which B is H or NH; are tested for rust preventing qualities using test method D-665 of the American Society for Testing Materials. Procedure B is followed using synthetic sea water. Briefly, the test consists of immersing an iron billet in a mixture of the oil composition and the 4 sea Water for 48 hours, and then examining the surface of the billet for rust.

For comparison, a control experiment in which no inhibitor is present is carried out. The following results are obtained.

TABLE Percent of Example Inhibitor Surface Rusted 1 Ammonium salt .2 0 None 45 Examples 3 and 4 Examples 1 and 2 are repeated except that the poly- (hexafluoropropylene oxide) oil is of the structure and has an average molecular Weight of 6,200. Similar results are obtained.

Although the invention has been described and exemplified by way of specific embodiments, it is to be understood that it is not limited thereto. As will be apparent to R OiECF C1 CF O-} CF CF R OiECF CF CF Oi CF CF CF (CF *EOCF CF (CF hOR;

where n, p and r are integers indicating the degree of polymerization and R, is a perfluoroalkyl group having 1 to 6 carbon atoms, said oil having an average molecular weight of at least 3,000 and a pour point not in excess 0 of 50 F. and, as rust inhibitor, an effective amount of perfluoroalkylether compound selected from the group consisting of acids and corresponding ammonium salts of the formula R O ECF CF CF oi CF (CF COOB in which m is 7 to 10, B is H or NH, and R; is as previously stated.

2. The composition of claim 1 in which the poly(hexafluoropropylene oxide) oil is of the formula and 0.1 to 2% by weight of perfluoroalkylether acid is present.

3. The composition of claim 2 in which R, is

the poly(hexafiuoropropylene oxide) oil has an average molecular weight of 5,500 to 7,000 and l to 2% of perfluoroalkylether acid is present.

4. The composition of claim 1 in which the poly(hexafluoropropylene oxide) oil is of the formula and 0.1 to 2% by weight of the ammonium salt of perfluoroalkylether acid is present.

5. The composition of claim 4 in which R; is

the poly(hexafluoropropylene oxide) oil has an average molecular weight of 5,500 to 7,000 and 1 to 2% of the and 0.1 to 2% by weight of perfluoroalkylether acid is present.

7. The composition of claim 6 in which R: is

CF CF CF the poly(hexafluoropropylene oxide) oil has an average molecular weight of 5,500 to 7,000 and 1 to 2% of perfiuoroalkylether acid is present.

8. The composition of claim 1 in which the poly(hexafluoropropylene oxide) oil is of the formula R OiECF CF CF O-Q CF (CF CF and 0.1 to 2% by weight of ammonium salt of perfluoroalkylether acid is present.

9. The composition of claim 8 in which R; is

CF CF CF the poly(hexafluoropropylene oxide) ,oil has an average molecular weight of 5,500 to 7,000 and 1. to 2% of the ammonium salt of perfluoroalkylether acid is present.

References Cited UNITED STATES PATENTS 3,242,218 3/1966 Miller 260535 15 DANIEL E. WYMAN, Primary Examiner W. H. CANNON. Assistant Examiner.

Claims (1)

1. A POLY(HEXAFLUOROPROPYLENE OXIDE) OIL COMPOSITION WHICH COMPRISES, AS THE BASE, A MAJOR AMOUNT OF POLY(HEXAFLUOROPROPYLENE OXIDE) OIL OF THE FORMULA
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4657687A (en) * 1985-02-14 1987-04-14 Montedison S.P.A. Lubricating compositions having improved film-forming properties
US4721795A (en) * 1984-06-19 1988-01-26 Montedison S.P.A. Fluoropolyethers containing end groups endowed with anchoring capacity
US5154845A (en) * 1987-08-10 1992-10-13 Pcr Group, Inc. Fluorine containing lubricating composition for relatively moving metal surfaces
US5169548A (en) * 1988-04-13 1992-12-08 Ausimont S.R.L. Antirust additives for lubricants or greases based on perfluoropolyethers
US5174916A (en) * 1987-03-02 1992-12-29 Gordon Osgood Lubricant additive composition containing nonionic fluorochemical polymer and method of using same
US5190681A (en) * 1988-04-13 1993-03-02 Ausimont S.R.L. Antirust additives for lubricants or greases based on perfluoropolyethers
WO1999051612A1 (en) * 1998-04-07 1999-10-14 E.I. Du Pont De Nemours And Company Phosphorus compounds as corrosion inhibitors for perfluoropolyethers
WO2002026686A1 (en) * 2000-09-27 2002-04-04 Asahi Glass Company, Limited Process for producing acyl fluoride and carboxylic acid salt
US20030015304A1 (en) * 2001-07-02 2003-01-23 Karl-Heinz Beuermann Method and device for degassing a suspension, specifically a fiber stock suspension
US6638622B2 (en) 2001-01-11 2003-10-28 Hitachi Global Storage Technologies Perfluorinated polyethers with metal carboxylate end groups as anti-wetting and corrosion-protective agents
US6828284B2 (en) 2001-08-06 2004-12-07 E. I. Du Pont De Nemours And Company Flourinated compositions comprising phosphorus
US7737094B2 (en) 2007-10-25 2010-06-15 Afton Chemical Corporation Engine wear protection in engines operated using ethanol-based fuel
US20120255651A1 (en) * 2011-04-07 2012-10-11 E.I. Du Pont De Nemours And Company Fluoroalkylalkoxylates
US20120259143A1 (en) * 2011-04-07 2012-10-11 E.I. Du Pont De Nemours And Company Fluoroalkylalkoxylates

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3242218A (en) * 1961-03-29 1966-03-22 Du Pont Process for preparing fluorocarbon polyethers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3242218A (en) * 1961-03-29 1966-03-22 Du Pont Process for preparing fluorocarbon polyethers

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4721795A (en) * 1984-06-19 1988-01-26 Montedison S.P.A. Fluoropolyethers containing end groups endowed with anchoring capacity
US4657687A (en) * 1985-02-14 1987-04-14 Montedison S.P.A. Lubricating compositions having improved film-forming properties
US5174916A (en) * 1987-03-02 1992-12-29 Gordon Osgood Lubricant additive composition containing nonionic fluorochemical polymer and method of using same
US5154845A (en) * 1987-08-10 1992-10-13 Pcr Group, Inc. Fluorine containing lubricating composition for relatively moving metal surfaces
US5169548A (en) * 1988-04-13 1992-12-08 Ausimont S.R.L. Antirust additives for lubricants or greases based on perfluoropolyethers
US5190681A (en) * 1988-04-13 1993-03-02 Ausimont S.R.L. Antirust additives for lubricants or greases based on perfluoropolyethers
WO1999051612A1 (en) * 1998-04-07 1999-10-14 E.I. Du Pont De Nemours And Company Phosphorus compounds as corrosion inhibitors for perfluoropolyethers
US6559108B1 (en) 1998-04-07 2003-05-06 E.I. Du Pont De Nemours And Company Perfluoropolyether compounds as magnetic media lubricants
WO2002026686A1 (en) * 2000-09-27 2002-04-04 Asahi Glass Company, Limited Process for producing acyl fluoride and carboxylic acid salt
EP1323702A4 (en) * 2000-09-27 2005-12-07 Asahi Glass Co Ltd Process for producing acyl fluoride and carboxylic acid salt
EP1323702A1 (en) * 2000-09-27 2003-07-02 Asahi Glass Company Ltd. Process for producing acyl fluoride and carboxylic acid salt
US6932890B2 (en) 2001-01-11 2005-08-23 International Business Machines Corporation Method for making a magnetic recording disk having a corrosion-protective layer of a perfluorinated polyether acid
US20040021984A1 (en) * 2001-01-11 2004-02-05 Qing Dai Magnetic recording head having a corrosion-protective layer of a metal salt of a perfluorinated polyether acid
US20040023076A1 (en) * 2001-01-11 2004-02-05 Qing Dai Process for synthesizing perfluorinated polyethers with metal carboxylate end groups
US20040023033A1 (en) * 2001-01-11 2004-02-05 Qing Dai Method for making a magnetic recording disk having a corrosion-protective layer of a perfluorinated polyether acid
US6940692B2 (en) 2001-01-11 2005-09-06 International Business Machines Magnetic recording head having a corrosion-protective layer of a metal salt of a perfluorinated polyether acid
US6916955B2 (en) 2001-01-11 2005-07-12 International Business Machines Process for synthesizing perfluorinated polyethers with metal carboxylate end groups
US6638622B2 (en) 2001-01-11 2003-10-28 Hitachi Global Storage Technologies Perfluorinated polyethers with metal carboxylate end groups as anti-wetting and corrosion-protective agents
US20030015304A1 (en) * 2001-07-02 2003-01-23 Karl-Heinz Beuermann Method and device for degassing a suspension, specifically a fiber stock suspension
US6828284B2 (en) 2001-08-06 2004-12-07 E. I. Du Pont De Nemours And Company Flourinated compositions comprising phosphorus
US7737094B2 (en) 2007-10-25 2010-06-15 Afton Chemical Corporation Engine wear protection in engines operated using ethanol-based fuel
US20120255651A1 (en) * 2011-04-07 2012-10-11 E.I. Du Pont De Nemours And Company Fluoroalkylalkoxylates
US20120259143A1 (en) * 2011-04-07 2012-10-11 E.I. Du Pont De Nemours And Company Fluoroalkylalkoxylates

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