US2971911A - Corrosion-resistant lubricating grease compositions - Google Patents
Corrosion-resistant lubricating grease compositions Download PDFInfo
- Publication number
- US2971911A US2971911A US726633A US72663358A US2971911A US 2971911 A US2971911 A US 2971911A US 726633 A US726633 A US 726633A US 72663358 A US72663358 A US 72663358A US 2971911 A US2971911 A US 2971911A
- Authority
- US
- United States
- Prior art keywords
- grease
- corrosion
- water
- weight
- imidazoline
- 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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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23Q—DETAILS, COMPONENTS, OR ACCESSORIES FOR MACHINE TOOLS, e.g. ARRANGEMENTS FOR COPYING OR CONTROLLING; MACHINE TOOLS IN GENERAL CHARACTERISED BY THE CONSTRUCTION OF PARTICULAR DETAILS OR COMPONENTS; COMBINATIONS OR ASSOCIATIONS OF METAL-WORKING MACHINES, NOT DIRECTED TO A PARTICULAR RESULT
- B23Q15/00—Automatic control or regulation of feed movement, cutting velocity or position of tool or work
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23B—TURNING; BORING
- B23B47/00—Constructional features of components specially designed for boring or drilling machines; Accessories therefor
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M5/00—Solid or semi-solid compositions containing as the essential lubricating ingredient mineral lubricating oils or fatty oils and their use
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
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- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/08—Inorganic acids or salts thereof
- C10M2201/082—Inorganic acids or salts thereof containing nitrogen
- C10M2201/083—Inorganic acids or salts thereof containing nitrogen nitrites
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- C10M2201/086—Chromium oxides, acids or salts
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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
- C10M2203/108—Residual fractions, e.g. bright stocks
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- 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
- C10M2207/022—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms containing at least two hydroxy groups
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- 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
- C10N2010/02—Groups 1 or 11
-
- 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
-
- 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
- C10N2010/06—Groups 3 or 13
-
- 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
- C10N2010/08—Groups 4 or 14
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- This invention relates to lubricating grease compositions. More particularly, it relates to grease compositions containing certain classes of oil-soluble imidazolines and alkali metal nitrites, the grease being gelled with a soap of substantially saturated hydroxy fatty materials.
- Grease compositions broadly comprise a lubricating oil gelled to a grease consistency with a gelling agent which may be an inorganic colloid or, more commonly, relatively high molecular weight metallic soaps. Under the conditions where greases are employed, these compositions are continuously or intermittently subjected to humid or wet atmospheres which provide an aqueous environment which, even in relatively small amounts, permits the corrosion of metallic surfaces being lubricated.
- a gelling agent which may be an inorganic colloid or, more commonly, relatively high molecular weight metallic soaps.
- these compositions are continuously or intermittently subjected to humid or wet atmospheres which provide an aqueous environment which, even in relatively small amounts, permits the corrosion of metallic surfaces being lubricated.
- Several mean of avoiding or minimizing these corrosion phenomena have been investigated, such as the use of corrosion resistant alloys, the coating of metal parts (such as metal bearings) with relatively permanent plastic or metallic coatings, the sealing of bearings to prevent the entry of water vapor, and the incorporation of corrosion inhibit
- Corrosion inhibitors are materials well known in the lubricating art and in allied arts wherein metallic equipment must be protected from destructive results of corrosive conditions. Corrosion inhibitors are believed to perform their function by several different mechanisms, such as the formation of monomolecular films either by reaction with or adsorption on the metallic surfaces.
- the corrosion inhibitor may be oil-soluble or watersoluble, but since corrosion appears to proceed with greatest rapidity in an aqueous medium, the most effective corrosion inhibitors for most situations are those possessing a substantial amount of water-solubility. The latter class is satisfactory, however, only when the greases are utilized for the protection of metallic surfaces under static or quiescent conditions.
- the problem of non-homogeneity of the grease is not only restricted to a settling of the corrosion inhibitors to the bottom of a storage container, but also is evidenced in an unsatisfactory property referred to as graininess.
- graininess By this is meant the phenomenon of crystal growth of the corrosion inhibitor in the grease composition to such an extent that the crystals are screened out of the grease when the latter is passed through a homogenizing screen toward the end of its manufacturing process. This results in a clogging of the screens and, more importantly, removal of the corrosion inhibitor from the grease composition, leaving the grease deficient in corrosion protec tive properties.
- lithium hydroxy fatty acid soap greases are favored for their excellent properties in other respects, they have been found to permit an undue amount of corrosion due to their frequent complete loss of amnity for metal surfaces when the grease has adsorbed water to the saturation point even though the grease may still maintain a good consistency.
- This lack of aflinity for metal prevents the grease under wet operating conditions from adhering to the metallic surface and not protecting them from corrosion. It also allows the grease to be easily squeezed or worked out of the bearings leaving them dry of grease with subsequent failure due to the lack of lubrication. This is especially evident under oscillating type of motion, but it also is a major cause of corrosion under static conditions as well.
- the lack of afiinity of lithium hydroxy fatty acid soap greases for metal allows a film of water to formvbetwcen the grease and the metallic surface and, unless steps are taken to counteract this, results in severe corrosion of the bearing surface.
- water-soluble corrosion inhibitors such as the nitrites
- nitrites The incorporation of water-soluble corrosion inhibitors, such as the nitrites, involves the initial difiiculty of dispersing the water-soluble material into a normally bydrophobic lubricating oil medium. This has been effected as referred to hereinbefore by the presence of emulsifying or dispersing agent, the nitrite being initially dissolved in an aqueous medium.
- the addition of an aqueous solution of sodium nitrite to a grease has adverse side effects, particularly insofar as the yield of the grease is concerned as well as changes in penetration when the water is gradually eliminated during ceremoni tion of the grease.
- any method which minimizes the amount of water necessary for the incorporation of the nitrite in a grease or more particularly, any method which enables the reduction in the amount of bothnitriteandwaterinthegreasewhilestillmaintaining the corrosion characteristics desired will be an economic mud-technical advantage.
- a further object of the invention is to enable the reduction in the amount of water-solublccorrosion inhibitor and of water in the grease.
- water-soluble alkali metal nitrites may be efiectively and permanently dispersed in greases gelled with soaps of hydroxy fatty acids by also mcorporating in said greases an amount between about 0.25
- the nitrites are present in the composition in the form of an aqueous solution, and, still in accordance with the invention, the presence of the imidazolines enables a reduction in the amount of nitrite while still maintaining the same degree of corrosion inhibition in the composition. More specifically, it has been found that the presence of the imidazolines not only prevents the separation of nitrite from the grease composition but also reduces the nitrite and water requirement to such an extent that the penetration of the grease is not adversely affected. This-has been brought about by the use of as little as about 20% by weight of the imidazoline compared with the weight of surfactants previously employed for nitrite dispersion.
- the water-soluble nitrites to be' utilized in accordance with the present invention are well known for their corrosion inhibiting properties. They comprise especially the alkali metal nitrites, such as sodium nitrite, potassium nitrite, and lithium nitrite. They may be supplemented by other nitrites, such as the organic nitrites including ammonium nitrites, such as dicyclohexylammonium nitrite or by chromates, such as sodium or potassium dichromate or the ammonium chromates. Due to the presence of the imidazolines, the amount of nitrite "is substantially smaller than that previously found to be necessary and is normally in the order of 0.051%, usually 0.'075-0.25% by weight of the grease composition.
- the lubricating oils to be employed in the preparation of the subject greases are any of the well-known hydrophobic oils of lubricating viscosity. These include not only mineral lubricating oil but also the aliphatic diesters, phosphates, aliphatic esters of pentaerythritol, silicates, siloxanes and oxalkyl ethers and esters.
- the mineral lubricating oil to be employed as the preferred major ingredient of the present grease compositions may be of any suitable lubricating viscosity, ranging from about 50 SSU at 100' F. to about 2000 SSU at 100 F.
- the viscosity index of the oil can vary from below 0 to about 100 or higher and the oil can have average molecular weights ranging from about 250 to about 800. It may be highly refined and solvent treated if desired by known means.
- the hydrocarbon oil may be of synthetic or mineral origin, although mineral oils are preferred.
- oils having viscosity indices above about 70 and preferably within the range of about 75 to about 95 are preferred for various reasons to employ oils having viscosity indices above about 70 and preferably within the range of about 75 to about 95.
- oils'derivegl from bright stock e.g. residual lubricating oils, comprise at least one-half of the lubricating oil components.
- the lubricating oils may be composed solely of mineral oil lubricants or may be replaced by or mixed with other hydrophobic lubricants, including tricresyl phosphate, trioctvl phosphate, tributyl phosphate; diesters such as bis-Z-ethylhexyl sebacate, bis-dinonyl adipate;.pentaerythritol esters, such as;C;C alltyl mixed pentaerythritol esters; tetrahexyl pentaerythritol esters; silicates, such as tetraoctyl silicate; polyoxyalltylene compounds, such as ethylene oxide propylene oxide copoly'mer's in which the end ,groups are either esterified o'r etherifiedysilicone oils, such as dimethyl silicone, methylphenyl silicone or chlorinated methylphenyl silicone and'other similar lubricating oils.
- the most effective classes comprise the N-alkylol-Z-alkyl (or alkenyl) imidazolines and the corresponding N-amino alkyl-Z-alkyl (or alkenyl) imidazolines.
- the hydroxy alkyl groups contains from 2 to 12 carbon atoms while the amino alkyl groups contain from 4 to 20 carbon atoms. Any alkyl or alkenyl substituents positioned elsewhere in the molecule and preferably on the two position contain from 11 to 21 carbon atoms each so as to promote oil solubility.
- lmidazolines useful in the present composition include the simple alkyl imidazolines, since it has been found that these promote the possibility of reducing the nitrite requirement while still maintaining corrosion inhibition in the grease composition.
- Suitable imidazolines include particularly Z-heptadecenyl imidazoline, 2-octadecenyl imidazoline, 2-dodecyl imidazoline, 2-octyl imidazoline, and Z-undecyl imidazoline.
- Amino imidazolines include especially those having the general structure l 5 4L B-Nl 3.
- R is an aliphatic, cyclic or mixed cyclicaliphatic amino group having at least one basic nitrogen atom, and preferably having at least two basic nitrogen atoms which can be primary, secondary or teritary, in any combination of the three.
- one or more of the nitrogens is primary, i.e., NH,. they can be attached at any position in an aliphatic chain or on a cyclic ring.
- one or more of the nitrogens is secondary or tertiary, they can be substituted in a straight or branched aliphatic chain, or in a heterocyclic ring, which can itself bear alkyl.
- R can be a mono, dior tri-ethylene amino group, or a l-alkylene imidazoline group, or a l-alkylene amino imidazoline group.
- R is an alkyl, hydroxyalkyl, alkenyl or hydroxyalkenyl group.
- Typical species of the hydroxyalkyl imidazolines include N-hydroxypropyl 2-tetradecyl imidazoline, N-h'ydroxybutenyl-Z-dodecyl imidazoline, N-dihydroxypropyl- Z-heptadecyl imidazoline, 2-hydroxyethvl-2-heptadecyl imidazoline, N-hydroxyethyl-Z-undecyl imidazoiine and N- hydroxyethyl-Z-heptadecenyl imidazoline.
- the soaps utilized as the principal gelling agent for the present invention comprise the soaps of hydroxy fatty acids having between about 12 and 24 carbon atoms per molecule. These are typified by the acids derived by saponification of the hydrogenated castor oil acids, principally IZ-hydroxystearic acid. The glycerides, methyl esters or the free acids may be employed in the saponification procedures.
- the soap may be formed in situ or may be preformed prior to incorporation together with other grease-forming ingredients.
- Suitable hydroxy fatty acids include 9,10-dihydroxystearic acid, 4-hydroxy- Imidazolines 0.252 Alkali metal nitrites 0.05-1 Soaps of hydroxy acids 5-25 Lubricating oil Balance Any other well-known grease additives may be employed, such as oxidation inhibitors and metal deactivators.
- the static corrosion protection of the subject class of greases was determined by the "glass jar corrosion test which is conducted as follows: Bearings are thoroughly washed in petroleum ether and dried to remove the oil and preservative with which they are usually packaged by the manufacturer. The bearing is then packed with the grease to be tested, being sure that it is well worked into the space behind the rolls on the cone and a small amount spread over the entire surface of the hearing. The assembled bearing is then placed in the Martinez pressure corrosion unit and 100 pounds pressure applied. It is then rotated at 500 r.p.m. for one minute. The bearmg is removed from the pressure unit, caution being taken that the cone and cup do not separate or turn from the position at which the rotation is stopped. The ex-' cess grease is wiped off but leaving a good coating on all surfaces.
- a small spatula is then used to remove grease at the opening of the annular space between the rolls and the cup to permit ready access for the water which is to be applied.
- the assembled bearing is then placed in a flat bottom glass jar which is one to two inches larger in diameter than the test bearing and three to four inches high. This jar must be fitted with an air tight cover. Twelve cubic centimeters of distilled water containing 0.05% w. NaCl is then run over the hearing by means of a pipette, making sure that a major portion goes into the space between the rolls and raceway. The jar is closed and allowed to stand undisturbed at room temperature for a period of 120 hours. At this time the test is completed and the bearing is ready to be removed for examination.
- the base grease namely, a gelling amount of lithium l2-hydroxystearate (79% soap) in mineral lubricating oil containing no inhibitors permitted heavy cororsion to occur under these test conditions. It was necessary to incorporate at least 0.5% of sodium nitrite in the base grease together with a surface active agent not falling within the scope of the present invention to reduce the corrosion of the panel to a satisfactory level during the test period.
- the replacement of the above surface active agent with 0.5 by weight of N-hydroxyethyI-Z-heptadecyl imidazoline enabled the reduction of the nitrite to 0.1% by weight while still maintaining the same degree of corrosion inhibition during the test period. Since the nitrite is added in the form of a 10% water solution. it will be seen that the use of the imidazolines substantially reduces the amount of water which would necessarily be incorporated in the grease if the imidazoline were not present.
- a lubricating grease composition comprising a lubricating oil thickened to a grease consistency with about 5-25% by weight of soaps of substantially saturated hydroxy fatty material, 0.252% by weight of an oilsoluble imidazoline, and about 0.051% by weight of a water-soluble alkali metal nitrite.
- a lubricating grease composition comprising a mineral lubricating oil thickened to a grease consistency with about 525% by weight of lithium soaps of substantially saturated hydroxy fatty material, 0.25-2 percent by Weight of an oil-soluble N-hydroxyalkyl imidazoline, and about 0.05-1% by weight of a water-soluble alkali metal nitrite.
- a lubricating grease composition comprising a mineral lubricating oil thickened to a grease consistency with about 5-25% by weight of lithium soaps of substantially saturated hydroxy fatty material, 0.25-2 percent by weight of an oil-soluble N-aminoalkyl imidazoline, and about 0.05-1% by weight of a water-soluble alkali metal nitrite.
- a lubricating grease composition comprising a mineral lubricating oil thickened to a grease consistency with about 5-25% by weight of lithium soaps of hydrogenated castor oil acids, 0.25-2 percent by weight of an oilsoluble imidazoline having the formula HgC-CH;
- R is an alkylol group and R is selected from the group consisting of alkyl and alkenyl, and about 0.05-l% by weight of sodium nitrite.
- a lubricating grease composition comprising a mineral lubricating oil thickened to a grease consistency with about 7-10% by weight of lithium soaps of hydrogenated castor oil acids, 0.25-2 percent by weight of l-N- hydroxyethyl 2 heptadecenyl imidazoline and 0.075- 0.25% by weight of sodium nitrite.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Drilling And Boring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS882506X | 1958-03-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2971911A true US2971911A (en) | 1961-02-14 |
Family
ID=5456507
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US726633A Expired - Lifetime US2971911A (en) | 1958-03-12 | 1958-04-07 | Corrosion-resistant lubricating grease compositions |
Country Status (5)
Country | Link |
---|---|
US (1) | US2971911A (fr) |
DE (1) | DE1121760B (fr) |
FR (2) | FR1222009A (fr) |
GB (2) | GB882506A (fr) |
NL (1) | NL237818A (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3231494A (en) * | 1961-08-22 | 1966-01-25 | Exxon Research Engineering Co | Rust preventive prepared from sodium nitrite and the reaction product of fatty acid and imidazoline |
US3291731A (en) * | 1962-02-05 | 1966-12-13 | Exxon Research Engineering Co | Incorporating sodium nitrite into lubricant compositions |
US3340206A (en) * | 1964-12-22 | 1967-09-05 | Exxon Research Engineering Co | Method of forming finely divided inorganic acid salts |
US20160347988A1 (en) * | 2015-06-01 | 2016-12-01 | King Fahd University Of Petroleum And Minerals | 2-(p-ALKOXYPHENYL)-2-IMIDAZOLINES AND THEIR USE AS CORROSION INHIBITORS |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2466517A (en) * | 1948-01-10 | 1949-04-05 | Petrolite Corp | Processes for preventing corrosion and corrosion inhibitors |
US2599384A (en) * | 1950-04-08 | 1952-06-03 | Petrolite Corp | Solid stick corrosion inhibitors and a process for preventing corrosion of oil and gas well equipment |
US2648633A (en) * | 1950-12-19 | 1953-08-11 | Shell Dev | Grease compositions |
US2661296A (en) * | 1948-04-26 | 1953-12-01 | Shell Dev | Rust inhibiting composition |
US2711393A (en) * | 1951-08-04 | 1955-06-21 | Standard Oil Co | Thickened lubricants |
US2732345A (en) * | 1956-01-24 | Soluble oils | ||
US2738329A (en) * | 1952-01-30 | 1956-03-13 | Shell Dev | Production of greases having elevated dropping points |
GB782879A (en) * | 1955-03-19 | 1957-09-11 | Exxon Standard Sa | Anti-corrosion compositions |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2581132A (en) * | 1949-07-13 | 1952-01-01 | Texas Co | Lubricating oil |
US2622018A (en) * | 1949-10-19 | 1952-12-16 | Socony Vacuum Oil Co Inc | Motor fuel |
US2655476A (en) * | 1951-10-26 | 1953-10-13 | Standard Oil Co | Thickened lubricants |
US2668100A (en) * | 1951-11-15 | 1954-02-02 | Nat Aluminate Corp | Corrosion inhibitor for liquid hydrocarbons |
US2773879A (en) * | 1952-04-02 | 1956-12-11 | Nat Aluminate Corp | Glyoxalidine salts of long chain dicarboxylic acids |
BE537231A (fr) * | 1954-04-08 |
-
0
- NL NL237818D patent/NL237818A/xx unknown
-
1958
- 1958-04-07 US US726633A patent/US2971911A/en not_active Expired - Lifetime
-
1959
- 1959-03-11 GB GB8490/59A patent/GB882506A/en not_active Expired
- 1959-03-12 FR FR789168A patent/FR1222009A/fr not_active Expired
- 1959-04-06 GB GB11566/59A patent/GB849799A/en not_active Expired
- 1959-04-06 DE DEN16512A patent/DE1121760B/de active Pending
- 1959-04-06 FR FR791296A patent/FR1222099A/fr not_active Expired
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2732345A (en) * | 1956-01-24 | Soluble oils | ||
US2466517A (en) * | 1948-01-10 | 1949-04-05 | Petrolite Corp | Processes for preventing corrosion and corrosion inhibitors |
US2661296A (en) * | 1948-04-26 | 1953-12-01 | Shell Dev | Rust inhibiting composition |
US2599384A (en) * | 1950-04-08 | 1952-06-03 | Petrolite Corp | Solid stick corrosion inhibitors and a process for preventing corrosion of oil and gas well equipment |
US2648633A (en) * | 1950-12-19 | 1953-08-11 | Shell Dev | Grease compositions |
US2711393A (en) * | 1951-08-04 | 1955-06-21 | Standard Oil Co | Thickened lubricants |
US2738329A (en) * | 1952-01-30 | 1956-03-13 | Shell Dev | Production of greases having elevated dropping points |
GB782879A (en) * | 1955-03-19 | 1957-09-11 | Exxon Standard Sa | Anti-corrosion compositions |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3231494A (en) * | 1961-08-22 | 1966-01-25 | Exxon Research Engineering Co | Rust preventive prepared from sodium nitrite and the reaction product of fatty acid and imidazoline |
US3291731A (en) * | 1962-02-05 | 1966-12-13 | Exxon Research Engineering Co | Incorporating sodium nitrite into lubricant compositions |
US3340206A (en) * | 1964-12-22 | 1967-09-05 | Exxon Research Engineering Co | Method of forming finely divided inorganic acid salts |
US20160347988A1 (en) * | 2015-06-01 | 2016-12-01 | King Fahd University Of Petroleum And Minerals | 2-(p-ALKOXYPHENYL)-2-IMIDAZOLINES AND THEIR USE AS CORROSION INHIBITORS |
US9816024B2 (en) * | 2015-06-01 | 2017-11-14 | King Fahd University of Pertoleum and Minerals | 2-(p-alkoxyphenyl)-2-imidazolines and their use as corrosion inhibitors |
US9868894B1 (en) | 2015-06-01 | 2018-01-16 | King Fahd University Of Petroleum And Minerals | Corrosion inhibition with alkoxy aromatic imidazolines |
Also Published As
Publication number | Publication date |
---|---|
NL237818A (fr) | |
FR1222099A (fr) | 1960-06-08 |
FR1222009A (fr) | 1960-06-07 |
GB882506A (en) | 1961-11-15 |
DE1121760B (de) | 1962-01-11 |
GB849799A (en) | 1960-09-28 |
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