US2160293A - Lubricant - Google Patents
Lubricant Download PDFInfo
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- US2160293A US2160293A US114434A US11443436A US2160293A US 2160293 A US2160293 A US 2160293A US 114434 A US114434 A US 114434A US 11443436 A US11443436 A US 11443436A US 2160293 A US2160293 A US 2160293A
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/16—Naphthenic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
- C10M2215/222—Triazines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
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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
- C10N2010/06—Groups 3 or 13
Definitions
- This invention relates to lubricants and in or tour nitrogen atoms only in the ring such as: particular, to "addition agents imparting improved pyrazole 1.2-diazo1e or pyrro (a) monazole) glyproperties to lubricants.
- oxaline or imidazcl 1.3-diazo1e
- 1,2,4-triazole This invention has particular utility in im- (pyrro (abi) diazole), 1,3,4-triazole (pyrro (bbi) proving the lubricating properties of lubricating diazole), 1 2,3-triazole (pyrro (ab) diazole), 1,2,5- 6 oils and/or in preventing or inhibiting the corrotriazole .
- pyrro (aai) diazole) 1,2,3;4-tetrazole sion of hard metal" alloy bearings such as cop- (pyrro (abbi) triazole), 1,2,3,5-tetrazole (pyrro.
- phenyl methyl ama-1 1. a i -1,2,5-t iv that highly refined lubricating oils cause corazoles, phenyl 1 2 3-t 1 h 1 ethoxy 1,2,3- 25 rosion t0 al y bearings the d mete-1 p triazoles, phenyl amino 1,2.3-triazoles, amino such as cadmium-Silver a oy e s t e X- methyl 1,2,3-triazoles, methyl 1,2,4-triazoles, tent of about 5 mg/cm.
- azine as used herein comprises the such or mixtures of g y refined lubricating Oils hexa-heterocyclic compounds having two or more with, less highly refined lubricating oils, or stated nitrogen atoms only in t g c in another way, mixtures of corrosive oils and ridazine (1,2-diazine or orthadiazine), pyrimi- 35 non-corrosive oils, examples of the latter bein dine (1,3-diazine or metadiazine), pyrazine (1,4- lubl'ieating Oil fractions from w elude diazine or paradiazine), as-triazine (1,2,4-tricrudes 0f the W k tyD azine), s-triazin'e (1,3,5-triazine or .cyanidine), We have found
- simble properties can be imparted to lubrlceiing the hereinbefore mentioned substituted derivaoils by adding thereto up to 5%, but preferab tives in which the following numbering system 0.05% to 0.75%, oi a poly membered heterocyclic is used: e
- A represents a heterocyclic radical selected N 46 from the group consisting of azoles containing (6) (2) only nitrogen and carbon in the ring, azines containing only nitrogen and carbon in the ring, (5) (3) pyrroles and thiophenes, and R.
- azole as used herein comprises the pyrimidines, methyl ethyl pyrimidines methyl penta heterocyclic compounds having two, three phenyl pyrimidines, dimethyl amino pyr midines, 55
- amino pyrimidines chloro dimethyl pyrimidines, 2,4,5,6-tetra chloro pyrimidine, methyl pyrazlnes, diphenyl pyrazines,'diphenyl methyl cyanidines, diphenyl cyanidines, triphenyl cyanidines, trimcthy] cyanidines, tributoxy cyanidines, chloro trimethyl cyanidines, amino cyanidines, diphenyl 1,2,3,4-tetrazine.
- thiophenes as used herein comprises the penta heterocyclic compounds having only sulfur and carbon in the ring of the general structural formula Y (i) and the hercinbefore mentioned substituted derivatives thereof, such as: lauryl thiophenes, dicyclohexyl thiophenes, isopropyl thiophenes, hexyl thiophenes, phenyl thiophenes, diphenyl thiophenes, tetraphenyl thiophenes, methyl plienyl thiophenes, aminothiophenes, thiophthens (bithiophenes).
- chlorothiophenes diamyl such as aluminum naphthenate, aluminum stearate and the like.
- a motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver, cadmium-nickel, copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said hard metal alloys and a small amount of a polymembered heterocyclic compound having the general formula A-R in which A represents a heterocyclic radical selected from the group consisting of azoles, containing only nitrogen and carbon in the ring, azines, containing only nitrogen and carbon in the ring, pyrroles and thiophenes and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small butsuflicient quantities to inhibit the corrosion of said hard
- a motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmium silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a' polymembered heterocyclic compound having the general formula AR in which -A represents an azole containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a
- a motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a polymembered heterocyclic compound having the general formula A-R'in which A represents an azine containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small but sufiicient quantities to inhibit the corrosion of said hard metal alloy bearings.
- a motor oil non-corrosive to hard metal alloybearings having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a polymembered heterocyclic compound having the general formula A-R in which A represents a thiophene containing only nitrogen and carbon in the ring and R.
- a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small but sufiicient quantities to inhibit the corrosion of said hard metal alloy bearings.
- a motor oil non-corrosive to hard metal alloy bearings having corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and tributoxy cyanidine, said tributoxy cyanidine being used in small but sufficient quantities to inhibit the corrosion of said hard metal alloy bearings.
- a motor oil non-corrosive to hard metal alloy bearings having corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and hexyl thiophene, said hexyl thiophene being used in small but sufficient quantities to inhibit the corrosion of said hard metal alloy bearings.
- the method of preventing corrosion of bearing metal alloys having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver alloys, cadmium-nickel alloys, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding to said lubricating oil from about 0.05% to about of a polymembered heterocyclic compound having the general formula A-R. in which A represents a heterocyclic radical selected from the group consisting of azoles containing only nitrogen and carbon in the ring, azines containing only nitrogen and carbon in the ring, pyrroles and thiophenes and R is a.
- substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted mino radical and a. halogen.
- e 3 mium-silver alloys, cadmium-nickel alloys, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula A-R.
- A represents an azole containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
- the method of preventing corrosion of bearing metal alloys having the corrosive susceptibility of alloys of the class consisting of cadmium-silver alloys, cadmium-nickel alloys, and copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding to said lubricating oil from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula AR in which A represents azines containing only nitrogen and carbon in the ring and in which R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
- gines which comprises adding to said lubricating oil from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula A-R in which A represents thiophenes and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
Description
UNITED 's'r 'ras PAT-TENT: OFFICE.
LUBRICANT Bernard H. Shoemaker and Clarence M.-Loane,
Hammond, Ind., asslgnors to Standard Oil Company, Chicago, 111., a corporation of Indiana No Drawing. Application December 5. 1936, Serial No. 114334 V This invention relates to lubricants and in or tour nitrogen atoms only in the ring such as: particular, to "addition agents imparting improved pyrazole 1.2-diazo1e or pyrro (a) monazole) glyproperties to lubricants. oxaline or imidazcl (1.3-diazo1e), 1,2,4-triazole This invention has particular utility in im- (pyrro (abi) diazole), 1,3,4-triazole (pyrro (bbi) proving the lubricating properties of lubricating diazole), 1 2,3-triazole (pyrro (ab) diazole), 1,2,5- 6 oils and/or in preventing or inhibiting the corrotriazole .(pyrro (aai) diazole) 1,2,3;4-tetrazole sion of hard metal" alloy bearings such as cop- (pyrro (abbi) triazole), 1,2,3,5-tetrazole (pyrro. per-lead, cadmiumnickel and cadmium-silver (abai) triazoie); and the hereinbefore mentioned bearings which, we large extent, have replaced substituted derivatives in which the following 10 soft metal bearings, such as Babbitt metal, in numbering system is used; the trend toward internal combustion engines (3)) (2)).
having high compression ratios and increased! I acceleration and increased speed characteristics. The use oiXthe hard metal" bearings has crc- )01) (5)0 0 ted ubr eet n Corrosion Problems, D Examples of the substituted derivatives of the 15 40 alloy bearings can' be inhibited and highly del y in connection with highly refined 0115, o above are: n-octyl pyrazoles, phenyl pyrazoles, of which may be Ve y corrosive t0 bearings of phenyl dimethyl pyrazoles, di, tri and/or tetra the hard metal type. methyl pyrazoles, chlor pyrazoles, amino py- 7 .As used herein y fi i ng oil razoles, amino trimethyl pyrazoles, phenyl ethoxy means viscous o ls wh c v 8 minimum pyrazoles, methyl glyoxalines, phenyl glyoxalines, e-OSity of S- A 10 Oils d Oils having higher 4 5-methyl phenyl glyoxalines, chloro methyl viscosities, and which have been subjected to glyoxalihs, 4,5 diphenylgly0xa1lne-2-mercaptan, such refining processes that the paraflinicity of 5- 1111 eth l glyoxaline, phenyl 1,2,5-triaz0les, the oil is markedly increased. It has been found phenyl methyl ama-1 1. a i -1,2,5-t iv that highly refined lubricating oils cause corazoles, phenyl 1 2 3-t 1 h 1 ethoxy 1,2,3- 25 rosion t0 al y bearings the d mete-1 p triazoles, phenyl amino 1,2.3-triazoles, amino such as cadmium-Silver a oy e s t e X- methyl 1,2,3-triazoles, methyl 1,2,4-triazoles, tent of about 5 mg/cm. and even greater Wilen phenyl 1,3,4-triazoles, l-phenyl 1,2,3,4-tetrazole, such bearings are submerged for 25 hours orless l-methyl 1,2 3,4..1; 1; 1 i-phenyl-z methyl n a air agitated Oil Which has been DI'eOXidiZed 1,2 3,4-tetrazole, mercapto tetrazoles, amino tetat about 340 F. for 25 to 50 hours. The motor razoles, o ls h y b y refined lubricating 011$ The term azine as used herein comprises the such or mixtures of g y refined lubricating Oils hexa-heterocyclic compounds having two or more with, less highly refined lubricating oils, or stated nitrogen atoms only in t g c in another way, mixtures of corrosive oils and ridazine (1,2-diazine or orthadiazine), pyrimi- 35 non-corrosive oils, examples of the latter bein dine (1,3-diazine or metadiazine), pyrazine (1,4- lubl'ieating Oil fractions from w elude diazine or paradiazine), as-triazine (1,2,4-tricrudes 0f the W k tyD azine), s-triazin'e (1,3,5-triazine or .cyanidine), We have found that eorroswn of hard metal v-t-riazine (1,2,3-triazine), s-tetrazine (1,2,45-
tetrazine), v-tetrazine 1 2,3,4-tetrazine); and 40 simble properties can be imparted to lubrlceiing the hereinbefore mentioned substituted derivaoils by adding thereto up to 5%, but preferab tives in which the following numbering system 0.05% to 0.75%, oi a poly membered heterocyclic is used: e
compound having the general formula A-R in m which A represents a heterocyclic radical selected N 46 from the group consisting of azoles containing (6) (2) only nitrogen and carbon in the ring, azines containing only nitrogen and carbon in the ring, (5) (3) pyrroles and thiophenes, and R. represents hy- (4) 0 'drogen or a substituted radical or radicals, such v 50 as alkyl or aryl or aralkyl or alkoxy or mercapto Examples of derivatives of the above named or amino or substituted amino or halogenand/or compounds methyl p d zm pheny mix ures-thereon pyridazines, methyl phenyl pyridazines, methyl The term azole as used herein comprises the pyrimidines, methyl ethyl pyrimidines methyl penta heterocyclic compounds having two, three phenyl pyrimidines, dimethyl amino pyr midines, 55
engines.
amino pyrimidines, chloro dimethyl pyrimidines, 2,4,5,6-tetra chloro pyrimidine, methyl pyrazlnes, diphenyl pyrazines,'diphenyl methyl cyanidines, diphenyl cyanidines, triphenyl cyanidines, trimcthy] cyanidines, tributoxy cyanidines, chloro trimethyl cyanidines, amino cyanidines, diphenyl 1,2,3,4-tetrazine.
The term pyrrole as used herein, comprises the penta heterocyclic compounds having a 4 membered carbon chain united to a ring by a bivalent imino (NH=) group (sometimes called the imine group) and the hereinbefore mentioned substituted derivatives thereof such as: methyl pyrroles, ethyl pyrroles, isoamyl pyrroles, phenyl pyrroles, methyl phenyl pyrroles.
The term thiophenes as used herein comprises the penta heterocyclic compounds having only sulfur and carbon in the ring of the general structural formula Y (i) and the hercinbefore mentioned substituted derivatives thereof, such as: lauryl thiophenes, dicyclohexyl thiophenes, isopropyl thiophenes, hexyl thiophenes, phenyl thiophenes, diphenyl thiophenes, tetraphenyl thiophenes, methyl plienyl thiophenes, aminothiophenes, thiophthens (bithiophenes).
In addition to the hereinbefore mentioned types of compounds we may use other compounds closely related to the foregoing such as pyridine,'quinoline, brucine, thienyls such as dithienylmethane, thienyltriphenylmethane, and the like.
The effectiveness of these compounds as cori'osion inhibitors is demonstrated by the following test in which the inhibitor was subjected to conditions more severe than those encountered in the actual operation of internal combustion In this test weighed cadmium-silver alloy hearings were placed in containers containing a highly refined oil with and without the addition of the inhibitors and the oil air agitated and maintained at a temperature of about 341 F. At periodic intervals the bearings were removed from the oil baths, washed free 0? the oil and the loss in weight determined. Before being replaced in the oil-bath the bearings were polished bright, reweighed and again tested for predetermined periods. In this test the oil used was a 'motor oil refined to such an extent that a loss in weight of more than 5 ing/cm. is obtained in 25 hours or less on a cadmium-silver alloy bearing submerged in the air agitated oil at about 341 R, which oil had been preoxidized for 25 to 50 hours at about 341 F.
' In the table below are tabulated the results obtained in the above test using tributoxy cyanidine (1,3,5-triazine) as the inhibitor.
Loss in weight (mg/cm?) Periods Oil 1st, 24 2nd, 6 3rd, 16 hrs. hrs. hrs.
Control. 3. 59 5. 06 20. 5 Control-+02% tributoxy cyanidine 0. 24 0.00 0. 11
The above data illustrates the high inhibiting power of compounds of the type hereinbefore described.
chlorothiophenes, diamyl such as aluminum naphthenate, aluminum stearate and the like.
We do not wish to limit ourselves to the specific embodiments of our invention herein described except as defined by the app nded claims.
We claim 1. A motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver, cadmium-nickel, copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said hard metal alloys and a small amount of a polymembered heterocyclic compound having the general formula A-R in which A represents a heterocyclic radical selected from the group consisting of azoles, containing only nitrogen and carbon in the ring, azines, containing only nitrogen and carbon in the ring, pyrroles and thiophenes and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small butsuflicient quantities to inhibit the corrosion of said hard metal alloy bearings.
2. A motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmium silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a' polymembered heterocyclic compound having the general formula AR in which -A represents an azole containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a
mercapto radical, an amino radical, a substituted mino radical and a halogen, said polymembered heterocyclic compound being added in small but suflicient quantities to inhibit the corrosion of said hard metal alloy bearings.
3. A motor oil non-corrosive to hard metal alloy bearings having the corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a polymembered heterocyclic compound having the general formula A-R'in which A represents an azine containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small but sufiicient quantities to inhibit the corrosion of said hard metal alloy bearings.
4. A motor oil non-corrosive to hard metal alloybearings having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and a polymembered heterocyclic compound having the general formula A-R in which A represents a thiophene containing only nitrogen and carbon in the ring and R. is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen, said polymembered heterocyclic compound being added in small but sufiicient quantities to inhibit the corrosion of said hard metal alloy bearings.
5. A motor oil non-corrosive to hard metal alloy bearings having corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and tributoxy cyanidine, said tributoxy cyanidine being used in small but sufficient quantities to inhibit the corrosion of said hard metal alloy bearings.
6. A motor oil non-corrosive to hard metal alloy bearings having corrosive susceptibility of alloys of the class consisting of cadmium-silver, cadmium-nickel and copper-lead alloys consisting of a mineral lubricating oil normally corrosive to said bearings and hexyl thiophene, said hexyl thiophene being used in small but sufficient quantities to inhibit the corrosion of said hard metal alloy bearings.
7. The method of preventing corrosion of bearing metal alloys having the corrosive susceptibility of alloys of the class consisting of cadmiumsilver alloys, cadmium-nickel alloys, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding to said lubricating oil from about 0.05% to about of a polymembered heterocyclic compound having the general formula A-R. in which A represents a heterocyclic radical selected from the group consisting of azoles containing only nitrogen and carbon in the ring, azines containing only nitrogen and carbon in the ring, pyrroles and thiophenes and R is a. substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted mino radical and a. halogen.
8. The method of preventing corrosion of hearing metal alloys having the corrosive susceptibility of alloys 01' the class consisting of cad- CERTIFICATE OF Patent No. 2,160,295.
e 3 mium-silver alloys, cadmium-nickel alloys, copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula A-R. in which A represents an azole containing only nitrogen and carbon in the ring and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
9. The method of preventing corrosion of bearing metal alloys having the corrosive susceptibility of alloys of the class consisting of cadmium-silver alloys, cadmium-nickel alloys, and copper-lead alloys in the presence of highly refined lubricating oils in internal combustion engines which comprises adding to said lubricating oil from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula AR in which A represents azines containing only nitrogen and carbon in the ring and in which R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
10. The method of preventing corrosion of bearing metal alloys having the corrosive susceptibility of alloys of the class consisting of cadmium-silver alloys, cadmium-nickel alloys and copper-lead alloys in the presence of highly refined lubricating oils in internal combustion en:
gines which comprises adding to said lubricating oil from about 0.05% to about 5% of a polymembered heterocyclic compound having the general formula A-R in which A represents thiophenes and R is a substituent selected from the group consisting of hydrogen, an alkyl radical, an aryl radical, an aralkyl radical, an alkoxy radical, a mercapto radical, an amino radical, a substituted amino radical and a halogen.
BERNARD H. SHQEMAKER. CLARENCE M. LOANE.
CORRECTION. I
May 50, 1939.
BERNARD H. SHOEHAKER, El AL.
It is hereby certified that error appears in the printed specification of the above numbered patent requiring correctionos follows: Page 2, secondcolumn, line 1 .6, claim 2, for "mino" read amino; and that the said Letters Patent should be read with this correction therein that the some may conform to the record of the case in the Patent Office. I
Signed and seale'dthis 25th day or July A. n. 1939. I
(Seal) soda-y Van Arsdale, Acting (lomnisaioner of Patents.
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US114434A US2160293A (en) | 1936-12-05 | 1936-12-05 | Lubricant |
Applications Claiming Priority (1)
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US114434A US2160293A (en) | 1936-12-05 | 1936-12-05 | Lubricant |
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US2160293A true US2160293A (en) | 1939-05-30 |
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US114434A Expired - Lifetime US2160293A (en) | 1936-12-05 | 1936-12-05 | Lubricant |
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Cited By (47)
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US2466530A (en) * | 1947-05-07 | 1949-04-05 | Petrolite Corp | Process for preventing corrosion and corrosion inhibitor |
US2479513A (en) * | 1947-04-05 | 1949-08-16 | Socony Vacuum Oil Co Inc | Lubricating oil |
US2480832A (en) * | 1947-12-13 | 1949-09-06 | Socony Vacuum Oil Co Inc | 3-thienyl thioethers in lubricating compositions |
US2497067A (en) * | 1945-12-21 | 1950-02-14 | Socony Vacuum Oil Co Inc | Mineral oil composition containing a thenylamine |
US2500822A (en) * | 1947-02-27 | 1950-03-14 | Socony Vacuum Oil Co Inc | Thenaldimines |
US2500498A (en) * | 1946-07-11 | 1950-03-14 | Socony Vacuum Oil Co Inc | Lubricant |
US2518351A (en) * | 1947-05-28 | 1950-08-08 | Socony Vacuum Oil Co Inc | N (thiophenalkyl) arylamines in mineral oil |
US2522489A (en) * | 1947-12-30 | 1950-09-19 | Socony Vacuum Oil Co Inc | Trithienyl-trithio-orthoformate |
US2522490A (en) * | 1947-12-30 | 1950-09-19 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing trithienyl-trithio-orthoformate |
US2527334A (en) * | 1947-06-24 | 1950-10-24 | Socony Vacuum Oil Co Inc | Mineral lubricating oil containing alkali and alkaline earth metal salts of alkylated dibenzothiophene sulfonic acid |
US2528782A (en) * | 1946-02-08 | 1950-11-07 | Socony Vacuum Oil Co Inc | Lubricant |
US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
US2534223A (en) * | 1948-01-28 | 1950-12-19 | Socony Vacuum Oil Co Inc | Mineral oil composition containing thienyl sulfides |
US2540093A (en) * | 1948-07-21 | 1951-02-06 | Socony Vacuum Oil Co Inc | Thienylthiolesters in lubricating compositions |
US2544294A (en) * | 1948-01-28 | 1951-03-06 | Socony Vacuum Oil Co Inc | 3-thienyl sulfides |
US2560956A (en) * | 1947-05-03 | 1951-07-17 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing polymers of thiophene |
US2561780A (en) * | 1948-09-01 | 1951-07-24 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing thienylthioalcohols |
US2566611A (en) * | 1949-12-03 | 1951-09-04 | Socony Vacuum Oil Co Inc | Mineral oil composition containing an alkyl thienyl ketimine |
US2571332A (en) * | 1947-12-30 | 1951-10-16 | Socony Vacuum Oil Co Inc | Thiophenethiol-phosphorus halide reaction products in lubricating compositions |
US2571333A (en) * | 1947-12-30 | 1951-10-16 | Socony Vacuum Oil Co Inc | Thiophenethiols-phosphorus halide reaction products |
US2581626A (en) * | 1948-10-06 | 1952-01-08 | Socony Vacuum Oil Co Inc | Thienylthio carboxylic acids and thienylthio carboxylic acid esters in lubricating compositions |
US2592451A (en) * | 1948-01-12 | 1952-04-08 | Shell Dev | Vapor phase corrosion inhibition |
US2618605A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2618608A (en) * | 1952-09-12 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2618603A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2618606A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2619463A (en) * | 1949-03-03 | 1952-11-25 | Exxon Standard Sa | Extreme pressure lubricant |
US2620303A (en) * | 1949-07-09 | 1952-12-02 | California Research Corp | Mercaptothiazines as sulfur-corrosion inhibiting agents |
US2624707A (en) * | 1949-06-07 | 1953-01-06 | Shell Dev | Lubricating composition |
US2657217A (en) * | 1950-04-08 | 1953-10-27 | Monsanto Chemicals | Corrosion inhibitor |
US2676150A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
US2861044A (en) * | 1950-07-08 | 1958-11-18 | Lever Brothers Ltd | Polyphosphate composition containing tarnish inhibitor |
US2890170A (en) * | 1956-09-06 | 1959-06-09 | Dow Corning | Organosiloxane greases |
US2932615A (en) * | 1957-07-22 | 1960-04-12 | Texnco Inc | Extreme pressure lubricant |
US2936290A (en) * | 1957-06-14 | 1960-05-10 | Geigy Ag J R | Oxidizable organic compositions stabilized with hydrogenated pyrazoles |
US3041278A (en) * | 1959-03-10 | 1962-06-26 | Shell Oil Co | Method of preparing polyvalent metal petroleum sulfonates and mineral lubricating oil containing same |
US3094488A (en) * | 1959-11-23 | 1963-06-18 | Exxon Research Engineering Co | Radiation resistant mineral oils |
US3095377A (en) * | 1960-10-10 | 1963-06-25 | Gulf Research Development Co | Lubricating composition having a reduced coking tendency |
US3211729A (en) * | 1961-03-28 | 1965-10-12 | Ciba Ltd | 1:2:4-triazine compounds |
US3250711A (en) * | 1964-03-06 | 1966-05-10 | Shell Oil Co | Gear lubricant |
US3299090A (en) * | 1964-03-27 | 1967-01-17 | Merck & Co Inc | Nitroimidazoles |
US3316176A (en) * | 1967-04-25 | Paper making process | ||
FR2387968A1 (en) * | 1977-04-05 | 1978-11-17 | Ciba Geigy Ag | SULFUR DERIVATIVES OF 1,2,4-TRIAZOLE, USED AS LUBRICANT ADDITIVES |
US4306986A (en) * | 1980-11-03 | 1981-12-22 | Olin Corporation | Selected poly(oxyalkylated) pyrazoles and their use as corrosion inhibitors |
US5395538A (en) * | 1991-08-29 | 1995-03-07 | Mobil Oil Corporation | Alkylated thiophene lubricants |
US20100076156A1 (en) * | 2006-11-15 | 2010-03-25 | Sumitomo Bakelite Co., Ltd. | Photosensitive resin composition, insulating film, protective film, and electronic equipment |
-
1936
- 1936-12-05 US US114434A patent/US2160293A/en not_active Expired - Lifetime
Cited By (49)
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US3316176A (en) * | 1967-04-25 | Paper making process | ||
US2497067A (en) * | 1945-12-21 | 1950-02-14 | Socony Vacuum Oil Co Inc | Mineral oil composition containing a thenylamine |
US2528782A (en) * | 1946-02-08 | 1950-11-07 | Socony Vacuum Oil Co Inc | Lubricant |
US2500498A (en) * | 1946-07-11 | 1950-03-14 | Socony Vacuum Oil Co Inc | Lubricant |
US2500822A (en) * | 1947-02-27 | 1950-03-14 | Socony Vacuum Oil Co Inc | Thenaldimines |
US2479513A (en) * | 1947-04-05 | 1949-08-16 | Socony Vacuum Oil Co Inc | Lubricating oil |
US2560956A (en) * | 1947-05-03 | 1951-07-17 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing polymers of thiophene |
US2466530A (en) * | 1947-05-07 | 1949-04-05 | Petrolite Corp | Process for preventing corrosion and corrosion inhibitor |
US2518351A (en) * | 1947-05-28 | 1950-08-08 | Socony Vacuum Oil Co Inc | N (thiophenalkyl) arylamines in mineral oil |
US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
US2527334A (en) * | 1947-06-24 | 1950-10-24 | Socony Vacuum Oil Co Inc | Mineral lubricating oil containing alkali and alkaline earth metal salts of alkylated dibenzothiophene sulfonic acid |
US2480832A (en) * | 1947-12-13 | 1949-09-06 | Socony Vacuum Oil Co Inc | 3-thienyl thioethers in lubricating compositions |
US2522489A (en) * | 1947-12-30 | 1950-09-19 | Socony Vacuum Oil Co Inc | Trithienyl-trithio-orthoformate |
US2571333A (en) * | 1947-12-30 | 1951-10-16 | Socony Vacuum Oil Co Inc | Thiophenethiols-phosphorus halide reaction products |
US2522490A (en) * | 1947-12-30 | 1950-09-19 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing trithienyl-trithio-orthoformate |
US2571332A (en) * | 1947-12-30 | 1951-10-16 | Socony Vacuum Oil Co Inc | Thiophenethiol-phosphorus halide reaction products in lubricating compositions |
US2592451A (en) * | 1948-01-12 | 1952-04-08 | Shell Dev | Vapor phase corrosion inhibition |
US2534223A (en) * | 1948-01-28 | 1950-12-19 | Socony Vacuum Oil Co Inc | Mineral oil composition containing thienyl sulfides |
US2544294A (en) * | 1948-01-28 | 1951-03-06 | Socony Vacuum Oil Co Inc | 3-thienyl sulfides |
US2540093A (en) * | 1948-07-21 | 1951-02-06 | Socony Vacuum Oil Co Inc | Thienylthiolesters in lubricating compositions |
US2561780A (en) * | 1948-09-01 | 1951-07-24 | Socony Vacuum Oil Co Inc | Mineral oil compositions containing thienylthioalcohols |
US2581626A (en) * | 1948-10-06 | 1952-01-08 | Socony Vacuum Oil Co Inc | Thienylthio carboxylic acids and thienylthio carboxylic acid esters in lubricating compositions |
US2618603A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2618605A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2618606A (en) * | 1949-02-04 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2619463A (en) * | 1949-03-03 | 1952-11-25 | Exxon Standard Sa | Extreme pressure lubricant |
US2624707A (en) * | 1949-06-07 | 1953-01-06 | Shell Dev | Lubricating composition |
US2620303A (en) * | 1949-07-09 | 1952-12-02 | California Research Corp | Mercaptothiazines as sulfur-corrosion inhibiting agents |
US2566611A (en) * | 1949-12-03 | 1951-09-04 | Socony Vacuum Oil Co Inc | Mineral oil composition containing an alkyl thienyl ketimine |
US2657217A (en) * | 1950-04-08 | 1953-10-27 | Monsanto Chemicals | Corrosion inhibitor |
US2861044A (en) * | 1950-07-08 | 1958-11-18 | Lever Brothers Ltd | Polyphosphate composition containing tarnish inhibitor |
US2676150A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
US2618608A (en) * | 1952-09-12 | 1952-11-18 | Procter & Gamble | Detergent compositions containing metal discoloration inhibitors |
US2890170A (en) * | 1956-09-06 | 1959-06-09 | Dow Corning | Organosiloxane greases |
US2936290A (en) * | 1957-06-14 | 1960-05-10 | Geigy Ag J R | Oxidizable organic compositions stabilized with hydrogenated pyrazoles |
US2932615A (en) * | 1957-07-22 | 1960-04-12 | Texnco Inc | Extreme pressure lubricant |
US3041278A (en) * | 1959-03-10 | 1962-06-26 | Shell Oil Co | Method of preparing polyvalent metal petroleum sulfonates and mineral lubricating oil containing same |
US3094488A (en) * | 1959-11-23 | 1963-06-18 | Exxon Research Engineering Co | Radiation resistant mineral oils |
US3095377A (en) * | 1960-10-10 | 1963-06-25 | Gulf Research Development Co | Lubricating composition having a reduced coking tendency |
US3211729A (en) * | 1961-03-28 | 1965-10-12 | Ciba Ltd | 1:2:4-triazine compounds |
US3250711A (en) * | 1964-03-06 | 1966-05-10 | Shell Oil Co | Gear lubricant |
US3299090A (en) * | 1964-03-27 | 1967-01-17 | Merck & Co Inc | Nitroimidazoles |
FR2387968A1 (en) * | 1977-04-05 | 1978-11-17 | Ciba Geigy Ag | SULFUR DERIVATIVES OF 1,2,4-TRIAZOLE, USED AS LUBRICANT ADDITIVES |
FR2388041A1 (en) * | 1977-04-05 | 1978-11-17 | Ciba Geigy Ag | LUBRICANTS CONTAINING TRIAZOLIC DERIVATIVES |
US4306986A (en) * | 1980-11-03 | 1981-12-22 | Olin Corporation | Selected poly(oxyalkylated) pyrazoles and their use as corrosion inhibitors |
US5395538A (en) * | 1991-08-29 | 1995-03-07 | Mobil Oil Corporation | Alkylated thiophene lubricants |
US20100076156A1 (en) * | 2006-11-15 | 2010-03-25 | Sumitomo Bakelite Co., Ltd. | Photosensitive resin composition, insulating film, protective film, and electronic equipment |
US8604113B2 (en) * | 2006-11-15 | 2013-12-10 | Sumitomo Bakelite Co., Ltd. | Photosensitive resin composition, insulating film, protective film, and electronic equipment |
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