US3280035A - Oil compositions containing emulsioninhibiting acetylenic compounds - Google Patents

Oil compositions containing emulsioninhibiting acetylenic compounds Download PDF

Info

Publication number
US3280035A
US3280035A US273571A US27357163A US3280035A US 3280035 A US3280035 A US 3280035A US 273571 A US273571 A US 273571A US 27357163 A US27357163 A US 27357163A US 3280035 A US3280035 A US 3280035A
Authority
US
United States
Prior art keywords
oil
methyl
acetylenic
oil compositions
emulsioninhibiting
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
Application number
US273571A
Inventor
Francis J Bonner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ExxonMobil Oil Corp
Original Assignee
Mobil Oil Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mobil Oil Corp filed Critical Mobil Oil Corp
Priority to US273571A priority Critical patent/US3280035A/en
Application granted granted Critical
Publication of US3280035A publication Critical patent/US3280035A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C10M129/06—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
    • 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
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/26—Amines
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • 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
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • 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
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/045—Metal containing thio derivatives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • lubricating oil compositions containing detergent and/or other additives which promote emulsification of the oil with water may have such emulsifying tendencies reduced by adding to such compositions a surfactant organic compound having an acetylenic linkage, that is, an organic molecule having a triple bond carbon to carbon linkage (CEC).
  • a surfactant organic compound having an acetylenic linkage that is, an organic molecule having a triple bond carbon to carbon linkage (CEC).
  • CEC carbon to carbon linkage
  • the compounds contemplated herein are hydroxy-substituted or halogen-substituted acetylenic hydrocarbons which are oil soluble within the effective ranges of amounts prescribed herein and which are normally solids or liquids at room temperature. These compounds generally contain from about 5 to about 18 carbon atoms, preferably from 6 to 10 carbon atoms and conform to the general formula:
  • R represents a radical selected from the group consisting of hydrogen, a hydrocarbyl radical having from 3 to about 8 carbon atoms, a hydroxy-substituted hydrocarbyl radical containing from 3 to about 8 carbon atoms annd a chloro-substituted hydrocarbyl radical containing from about 3 to about 8 carbon atoms, at least one R being a hydroxyor chloro-substituted hydrocarbyl radical of from 3 to about -8 carbon atoms.
  • acetylenic compounds contemplated herein are the following:
  • Ethynyl cyclohexanol 3-methyl 1-nonyn-3-0l CEO-H The effectiveness of the invention has been demon strated by adding typical acetylenic'compounds to a lubricating oil composition and testing the resultant mixture for demulsibility, that is, the ability to obtain separation of water from oil-water mixtures.
  • the test procedure used is the standard ASTM procedure designated as D1401-56T, in which 40 ml. of the oil composition being tested is mixed with 40 ml. of distilled water and the mixture is stirred for 5 minutes at 130 F. in a graduated cylinder, after which the resulting emulsion is allowed to stand at room temperature so that theemulsion breaks and forms separate layers of water, oil and emulsion. The time for the emulsion to be reduced to 3 ml. or less is noted as the measure of demulsibility.
  • EXAMPLE 1 The first series of tests using this standard method were carried out with a fully formulated turbine circulating heavy oil composition containing about parts of solvent-refined turbine oil base stock, 0.04 part of a rust inhibitor comprising a reaction product of tetrapropenyl succinic anhydride and oleic acid-triethylenetetramine reaction product, prepared after the fashion of Example 2, US. Patent No. 2,568,876, 0.25 part of di-t-butyl paracresol as an antioxidant and 0.15 part of zinc dihexyldithiophosphate as an antioxidant.
  • the acetylenic compounds are added to the oil composition in the amounts shown, based on such composition, as set forth in Table 1, wherein the test results are shown.
  • A Heavy turbine circulating oil composition 59
  • B A+0.1% 3-methyl 1-pentyn-3-ol 51
  • C A+O.5% 3-methyl 1-pentyn-3-ol 52
  • D A+1.0% 3-methyl 1-pentyn-3-ol 50
  • E A+0.1% 3-chloro-3-methyl-l-pentyne 41
  • F A+O.5% 3-chloro-3-methyl-l-pentyne 34
  • G A+1.0% 3-chloro-3-methyl-l-pentyne 26
  • H A+0.1% ethynyl cyclohexanol 51 Time to 3 ml.
  • acetylenic demulsifiers are highly advantageous since it permits the compounding of oils with many desirable additives that otherwise would render the oil blends emulsive.
  • the invention is, therefore, not limited to the use of the acetylenic compounds with the specific additives shown in the tests.
  • the amount of acetylenic compound may vary Widely, ranging from about 0.1 to 10% of the weight of the oil blend or composition to which the compound is added. The range is preferably between about 0.1-5.0%. Higher amounts than about 10.0% are effective but may not be sufiiciently economical to justify their use.
  • the present invention is applicable to the various lubrieating oil compositions in which a base oil is blended with different detergents, corrosion inhibitors, antioxidants and the like.
  • These oil compositions chiefly because of these additives, tend to emulsify readily with water and the emulsions formed are difficult to break down so that oil can be separated from the water.
  • the inclusion of relatively small amounts of one or more of the acetylenic compounds in the oil compositions tends to prevent emulsification altogether or to rapidly demulsify such emulsions as may be formed.
  • a lubricating oil composition comprising a major proportion of a lubricating oil and a minor proportion, from about 0.1% to about 10% by weight, of an acetylenic compound selected from the group consisting of 3- methyl-1-nonyn-3-ol, 3-phenyl-1-butyn-3-ol, and 3-chloro- 3 -methyl-1-pe'ntyne.
  • composition of claim 1 wherein the acetylenic compound is 3methyl-1-nonyn-3-ol.
  • composition of claim 1, wherein the acetylenic compound is 3-phenyl-1-butyn-3-ol.
  • composition of claim 1 wherein the acetylenic compound is 3-chloro-3-methyl-l-pentyne.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)

Description

United States Patent 3,280,035 OIL COMPOSITIONS CONTAINING EMULSION- INHIBITING ACETYLENIC COMPOUNDS Francis J. Bonner, Wilmington, Del., assiguor to Mobil Oil Corporation, a corporation of New York No Drawing. Filed Apr. 17, 1963, Ser. No. 273,571
' 4 Claims. (Cl. 25252) pounded with various detergents, anti-rust agents, antioxidants and other additives which act as oil emulsifiers in the presence of water. It is desirable to obtain rapid separation and removal of any Water dispersed in the lubricating oil and this is usually accomplished by centrifuging and/or settling. Obviously, the formation of oil-water emulsions would interfere with any such separation of the water from the oil.
It is one of the objects of the present invention to inhibit the emulsifying tendencies of lubricating oils. It is another object to enhance the demulsibility of additivemodified lubricating oil compositions. It is a further object to add specific surfactants to the compounded lubricating oils to depress emulsification thereof in the presence of water. Other objects will be apparent from the following description in which parts and percentages, where used, are by weight.
According to the present invention, it has now been found that lubricating oil compositions containing detergent and/or other additives which promote emulsification of the oil with water may have such emulsifying tendencies reduced by adding to such compositions a surfactant organic compound having an acetylenic linkage, that is, an organic molecule having a triple bond carbon to carbon linkage (CEC). The compounds contemplated herein are hydroxy-substituted or halogen-substituted acetylenic hydrocarbons which are oil soluble within the effective ranges of amounts prescribed herein and which are normally solids or liquids at room temperature. These compounds generally contain from about 5 to about 18 carbon atoms, preferably from 6 to 10 carbon atoms and conform to the general formula:
Where R represents a radical selected from the group consisting of hydrogen, a hydrocarbyl radical having from 3 to about 8 carbon atoms, a hydroxy-substituted hydrocarbyl radical containing from 3 to about 8 carbon atoms annd a chloro-substituted hydrocarbyl radical containing from about 3 to about 8 carbon atoms, at least one R being a hydroxyor chloro-substituted hydrocarbyl radical of from 3 to about -8 carbon atoms.
Specific examples of the acetylenic compounds contemplated herein are the following:
Ethynyl cyclohexanol 3-methyl 1-nonyn-3-0l CEO-H The effectiveness of the invention has been demon strated by adding typical acetylenic'compounds to a lubricating oil composition and testing the resultant mixture for demulsibility, that is, the ability to obtain separation of water from oil-water mixtures. The test procedure used is the standard ASTM procedure designated as D1401-56T, in which 40 ml. of the oil composition being tested is mixed with 40 ml. of distilled water and the mixture is stirred for 5 minutes at 130 F. in a graduated cylinder, after which the resulting emulsion is allowed to stand at room temperature so that theemulsion breaks and forms separate layers of water, oil and emulsion. The time for the emulsion to be reduced to 3 ml. or less is noted as the measure of demulsibility.
EXAMPLE 1 The first series of tests using this standard method were carried out with a fully formulated turbine circulating heavy oil composition containing about parts of solvent-refined turbine oil base stock, 0.04 part of a rust inhibitor comprising a reaction product of tetrapropenyl succinic anhydride and oleic acid-triethylenetetramine reaction product, prepared after the fashion of Example 2, US. Patent No. 2,568,876, 0.25 part of di-t-butyl paracresol as an antioxidant and 0.15 part of zinc dihexyldithiophosphate as an antioxidant. The acetylenic compounds are added to the oil composition in the amounts shown, based on such composition, as set forth in Table 1, wherein the test results are shown.
TABLE 1 Time to 3 ml.
emul., min.
(A) Heavy turbine circulating oil composition 59 (B) A+0.1% 3-methyl 1-pentyn-3-ol 51 (C) A+O.5% 3-methyl 1-pentyn-3-ol 52 (D) A+1.0% 3-methyl 1-pentyn-3-ol 50 (E) A+0.1% 3-chloro-3-methyl-l-pentyne 41 (F) A+O.5% 3-chloro-3-methyl-l-pentyne 34 (G) A+1.0% 3-chloro-3-methyl-l-pentyne 26 (H) A+0.1% ethynyl cyclohexanol 51 Time to 3 ml.
' emul., min.
(I) A+0.5%'ethynyl cyclohexanol 52 (J) A+l.0% ethynyl cyclohexanol 46 (K) A+O.l% 3,5-dimethyl 1-heXyn-3-ol 50 (L) A+0.5% 3,5-dimethyl 1-hexyn-3-ol 47 (M) A+1.0% 3,5-dimethyl1-hexyn-3-ol 43 (N) A+0.l% 3-phenyl 1-butyn-3-o1 51 (O) A+0.5% '3-phenyl 1-butyn-3-ol 49 (P) All.0% 3-pheny11-butyn-3-ol 38 EXAMPLE 2 A second series of tests were carried out as in Example 1, using a somewhat lighter oil blend containing about 100 parts of a lubricating oil base stock, 0.2 part zine dihexyldithiophosphate as an antioxidant and 0.1 part of the same anti-rust agent used in Example 1, viz., the reaction product of tetrapropenyl succinic anhydride with the reaction product of triethylenetetramine and oleic acid. The results of these tests are shown in Table 2.
TABLE 2 Time to 3 ml. emul., min. (A) Lubricating oil blend 42 (B) A+1.0% S-methyl 1-pentyn-3-ol 36 (C) A+2.0% 3-methyl 1-pentyn-3-ol 36 (D) A+4.0% 3-methyl 1-pentyn-3-ol 35 (E) A+1.0% 3-methyl 1-nonyn-3-ol 25 (F) A+2.0% B-methyl 1-nonyn-3-ol 17 (G) A+4.0% 3-methyl 1-nonyn-3-ol 16 (H) A+1.0% 3,5-di-methyl 1-hexyn-3-ol 28 (I) A+2.0% 3,5-dimethyl 1-hexyn-3-ol 27 (J) A+4.0% 3,5-dimethyl l-hexyn-3-ol 24 (K) A+1.0% ethynyl cyclohexanol 24 (L) A+2.0% ethynyl cyclohexanol 25 (M) A+4.0% ethynylcyclohexanol 22 (N) A+l.0% 3-phenyl l-butyn-3-ol 27 (O) A+2.0% 3-phenyl1-butyn-3-ol 26 (P) A+0.5% 4-ethyl l-octyn-3-ol 32 (Q) A+1.0% 4-ethyl 1-octyn-3-ol 32 (R) A+1.5% 4-ethyl 1-octyn-3-ol 27 (S) A+2.0% 4-ethyl 1-octyn-3-ol 27 (T) A+0.2% 3,6-dirnethyl-4-octyn-3,6-diol 35 (U) A+0.3% 3,6-dimethyl-4-octyn-3,6-diol 27 It will be seen from Tables 1 and 2 that the acetylenic compounds of the invention are eflective de-emulsifiers.
It will be understood that other acetylenic compounds The use of the acetylenic demulsifiers is highly advantageous since it permits the compounding of oils with many desirable additives that otherwise would render the oil blends emulsive. The invention is, therefore, not limited to the use of the acetylenic compounds with the specific additives shown in the tests. The amount of acetylenic compound may vary Widely, ranging from about 0.1 to 10% of the weight of the oil blend or composition to which the compound is added. The range is preferably between about 0.1-5.0%. Higher amounts than about 10.0% are effective but may not be sufiiciently economical to justify their use.
The present invention is applicable to the various lubrieating oil compositions in which a base oil is blended with different detergents, corrosion inhibitors, antioxidants and the like. These oil compositions, chiefly because of these additives, tend to emulsify readily with water and the emulsions formed are difficult to break down so that oil can be separated from the water. The inclusion of relatively small amounts of one or more of the acetylenic compounds in the oil compositions tends to prevent emulsification altogether or to rapidly demulsify such emulsions as may be formed.
Having now fully described the invention, what is claimed as new and patentable is:
1. A lubricating oil composition comprising a major proportion of a lubricating oil and a minor proportion, from about 0.1% to about 10% by weight, of an acetylenic compound selected from the group consisting of 3- methyl-1-nonyn-3-ol, 3-phenyl-1-butyn-3-ol, and 3-chloro- 3 -methyl-1-pe'ntyne.
2. The composition of claim 1, wherein the acetylenic compound is 3methyl-1-nonyn-3-ol.
3. The composition of claim 1, wherein the acetylenic compound is 3-phenyl-1-butyn-3-ol.
4. The composition of claim 1, wherein the acetylenic compound is 3-chloro-3-methyl-l-pentyne.
References Cited by the Examiner UNITED STATES PATENTS 2,493,213 l/1950 Altarnura 252-35 2,997,447 8/1961 Russell 252-358 X 3,095,381 6/1963 Tinnon 252-33l X DANIEL E. WYMAN, Primary Examiner. C. O. THOMAS, W. H. CANNON, Assistant Examiners.

Claims (1)

1. A LUBRICATING OIL COMPOSITION COMPRISING A MAJOR PROPORTION OF A LUBRICATING OIL AND A MINOR PROPORTION, FROM ABOUT 0.1% TO ABOUT 10% BY WEIGHT, OF AN ACETYLENIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF 3METHYL-1-NONYN-3-OL, 3-PHENYL-1-BUTYN-3-OIL, AND 3-CHLORO3-METHYL-1-PENTYNE.
US273571A 1963-04-17 1963-04-17 Oil compositions containing emulsioninhibiting acetylenic compounds Expired - Lifetime US3280035A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US273571A US3280035A (en) 1963-04-17 1963-04-17 Oil compositions containing emulsioninhibiting acetylenic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US273571A US3280035A (en) 1963-04-17 1963-04-17 Oil compositions containing emulsioninhibiting acetylenic compounds

Publications (1)

Publication Number Publication Date
US3280035A true US3280035A (en) 1966-10-18

Family

ID=23044496

Family Applications (1)

Application Number Title Priority Date Filing Date
US273571A Expired - Lifetime US3280035A (en) 1963-04-17 1963-04-17 Oil compositions containing emulsioninhibiting acetylenic compounds

Country Status (1)

Country Link
US (1) US3280035A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2439815A1 (en) * 1978-10-27 1980-05-23 Pennwalt Corp METHOD FOR REDUCING THE RESIDUES OF NON-VOLATILE CARBON PRODUCTS RESULTING FROM THE TREATMENT, AT HIGH TEMPERATURE, OF A METAL SUBSTRATE WITH A TREATMENT COMPOSITION
US20070112079A1 (en) * 2005-11-17 2007-05-17 General Electric Company Emulsion breaking process

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493213A (en) * 1945-10-31 1950-01-03 Socony Vacuum Oil Co Inc Lubricant
US2997447A (en) * 1954-02-08 1961-08-22 Air Reduction Aqueous acetylenic glycol compositions
US3095381A (en) * 1959-08-28 1963-06-25 Air Reduction Cleaning compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2493213A (en) * 1945-10-31 1950-01-03 Socony Vacuum Oil Co Inc Lubricant
US2997447A (en) * 1954-02-08 1961-08-22 Air Reduction Aqueous acetylenic glycol compositions
US3095381A (en) * 1959-08-28 1963-06-25 Air Reduction Cleaning compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2439815A1 (en) * 1978-10-27 1980-05-23 Pennwalt Corp METHOD FOR REDUCING THE RESIDUES OF NON-VOLATILE CARBON PRODUCTS RESULTING FROM THE TREATMENT, AT HIGH TEMPERATURE, OF A METAL SUBSTRATE WITH A TREATMENT COMPOSITION
US4214924A (en) * 1978-10-27 1980-07-29 Pennwalt Corporation Method of improving surface characteristic of heat-treated metal
US20070112079A1 (en) * 2005-11-17 2007-05-17 General Electric Company Emulsion breaking process
US7612117B2 (en) * 2005-11-17 2009-11-03 General Electric Company Emulsion breaking process

Similar Documents

Publication Publication Date Title
US2977309A (en) Lubricating oil containing branched chain alkyl amine derivatives of dicarboxylic acids
US2455659A (en) Oily composition
US2680094A (en) Rust preventive oil composition
US3004916A (en) Lubricating oil
US2412634A (en) Lubricant
US2415353A (en) Rust preventing turbine oil
US3247110A (en) Fuel oil and lubricating oil compositions containing metal salts of the mono-amidesof tetrapropenyl succinic acid
US2967831A (en) Hydraulic fluid and its preparation
US2215590A (en) Lubricating composition
US3280035A (en) Oil compositions containing emulsioninhibiting acetylenic compounds
US2330773A (en) Lubricant
US2391087A (en) Oil solubilizing compositions
US3003960A (en) Glycine amic acids in turbine oil
US2810694A (en) Textile oil
US2934500A (en) Anti-corrosion compositions and mineral oil compositions containing the same
US2655478A (en) Noncorrosive soluble oil containing active sulfur
JPS6124436B2 (en)
US2779740A (en) Mineral oil lubricating compositions
US2230556A (en) Foam suppressor for soluble oils
US3929656A (en) Drawing oil
US2742432A (en) Mineral oil lubricating compositions
US2623887A (en) Rust inhibiting composition
US2662815A (en) Oxidation inhibitors
US2533700A (en) Nonfoaming lubricant composition
US2721846A (en) Flushing oil composition