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US4764298A
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Lubrication anti-wear additive
Assignee: Union Oil Company of California
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Filing: 1987-11-20
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Granted: 1988-08-16
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Expires: 2007-11-20
Abstract
Abstract An extreme pressure anti-wear additive soluble in lubricating oils is provided wherein the additive comprises the reaction product of a 2-mercaptobenzothiazole with (1) an aldehyde or ketone, preferably having between 1 and 10 carbon atoms, and (2) ammonia or an amine, preferably an amine containing between 8 and 40 carbon atoms. The reaction product formed is an ashless, metals-free, extreme pressure agent soluble in lubricating oils.
Inventors
- 👤 Michael C. Croudace
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 23:32
CPC Classifications
C; C10; C10M; C10M135/00; C10M135/32; C10M135/36; C07; C07D; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/74; C10M2219/00; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10N; C10N2040/00; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
106 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which method comprises admixing into said lubricating composition an extreme pressure enhancing amount of an anti-wear additive, said additive being the reaction product of (1) 2-mercaptobenzothiozole, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic aldehydes and ketones having between 2 and 20 carbon atoms, and (3) a nitrogen-containing compound selected from the group consisting of primary and secondary amines having between 8 and 40 carbon atoms, said reaction product being soluble in said oleaginous material at a concentration of at least 2.25 percent.
Claim 2
Independent Claim
106 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which method comprises admixing into said lubricating composition an extreme pressure enhancing amount of an anti-wear additive, said additive being the reaction product of (1) 2-mercaptobenzothiozole, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic aldehydes and ketones having between 2 and 20 carbon atoms, and (3) a nitrogen-containing compound selected from the group consisting of primary and secondary amines having between 8 and 40 carbon atoms, said reaction product being soluble in said oleaginous material at a concentration of at least 2.25 percent.
Claim 3
Dependent Claim
37 words
The method of claim 1 wherein said amine is selected from the group consisting of primary and secondary aliphatic and alicyclic amines and wherein the 2-mercaptobenzothiazole, carbonyl-containing compound, and amine are reacted in a 1:1:1 molar ratio.
Claim 4
Dependent Claim
15 words
The method of claim 2 wherein the amine is a dialkyl or dicycloalkyl secondary amine.
Claim 5
Dependent Claim
24 words
The method of claim 1 wherein the carbonyl-containing compound comprises substituents selected from the group consisting of alkoxy, hydroxy, mercapto, nitro, and halogen groups.
Claim 6
Dependent Claim
33 words
The method of claim 1 wherein the carbonyl-containing compound is an aldehyde selected from the group consisting of acetaldehyde, benzaldehyde, 2-ethylhexylaldehyde, butryaldehyde, capryl aldehyde, acryl aldehyde, crotonaldehyde, vinylacetaldehyde, phenylacetaldehyde, nitrobenzaldehyde, furfural, and chloral.
Claim 7
Dependent Claim
26 words
The method of claim 1 wherein the amine is selected from the group consisting of dihexylamine, dioctylamine, ditallowamine, dinonylamine, didodecylamine, dihexadecylamine, hexadecylamine, octadecylamine, dicyclohexylamine, and N-methyl-n-octadecylamine.
Claim 8
Dependent Claim
32 words
The method of claim 1 wherein the carbonyl-containing compound is a ketone selected from the group consisting of acetone, methylethyl ketone, methylhexyl ketone, dihexyl ketone, dioctyl ketone, dinonyl ketone, and didecyl ketone.
Claim 9
Independent Claim
212 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which comprises admixing into said lubricating composition an extreme pressure anti-wear enhancing amount of an ashless and metals-free compound of the formula: ##STR6## wherein: R 1 and R 2 are the same or different substituents selected from the group consisting of hydrogen and metals-free, substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the class consisting of oxygen, sulfur, and nitrogen atoms provided that R 1 and R 2 have a total of between about 8 and about 40 carbon atoms and are not both hydrogen; R 3 and R 4 are the same or different substituents selected from the group consisting of hydrogen and metal-free, substituted or unsubstituted alkyl, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, arylalkenyl, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the group consisting of oxygen, sulfur and nitrogen atoms provided that R 3 and R 4 have a total of between about 8 and 20 carbon atoms and are not both hydrogen; and R 5 is hydrogen or one or more organic substituents located on the benzene ring.
Claim 10
Independent Claim
212 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which comprises admixing into said lubricating composition an extreme pressure anti-wear enhancing amount of an ashless and metals-free compound of the formula: ##STR6## wherein: R 1 and R 2 are the same or different substituents selected from the group consisting of hydrogen and metals-free, substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the class consisting of oxygen, sulfur, and nitrogen atoms provided that R 1 and R 2 have a total of between about 8 and about 40 carbon atoms and are not both hydrogen; R 3 and R 4 are the same or different substituents selected from the group consisting of hydrogen and metal-free, substituted or unsubstituted alkyl, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, arylalkenyl, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the group consisting of oxygen, sulfur and nitrogen atoms provided that R 3 and R 4 have a total of between about 8 and 20 carbon atoms and are not both hydrogen; and R 5 is hydrogen or one or more organic substituents located on the benzene ring.
Claim 11
Dependent Claim
10 words
The method of claim 8 wherein R 3 is hydrogen.
Claim 12
Dependent Claim
19 words
The method of claim 8 wherein R 3 and R 4 independently contain between 0 and 10 carbon atoms.
Claim 13
Dependent Claim
21 words
The method of claim 8 wherein R 1 and R 2 independently contain between about 4 and about 50 carbon atoms.
Claim 14
Dependent Claim
26 words
The method of claim 1 wherein the oleaginous material is selected from the group consisting of lubricating oils or greases derived from mineral or synthetic oils.
Claim 15
Dependent Claim
19 words
The method of claim 1 wherein the oleaginous material comprises lubricating oils for use in gasoline-powered internal combustion engines.
Claim 16
Dependent Claim
28 words
The method of claim 1 wherein the extreme pressure enhancing amount is at least about 2.25 weight percent of the total amount of the compound and oleaginous material.
Claim 17
Dependent Claim
17 words
The method of claim 1 wherein said extreme pressure anti-wear enhancing reaction product is metals-free and ashless.
Claim 18
Independent Claim
166 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which method comprises admixing into said lubricating composition an extreme pressure, anti-wear enhancing amount of an ashless and metals-free additive having the formula: ##STR7## wherein R 1 and R 2 are independently organic radicals or hydrogen, provided that both R 1 and R 2 are not simultaneously hydrogen, and further provided that the total number of carbon atoms in R 1 and R 2 is between 8 and 40, R 3 and R 4 are independently organic radicals, bromine, chlorine or hydrogen, provided that at least one of R 3 and R 4 is an organic radical, and further provided that the total number of carbon atoms in R 3 and R 4 is between 1 and 20, and R 5 is selected from the group consisting of hydrogen and organic radicals, said additive being soluble in 450 neutral oil at a concentration of at least 2.25 weight percent.
Claim 19
Independent Claim
166 words
A method for enhancing the extreme pressure anti-wear characteristics of a lubricating composition comprising an oleaginous material, which method comprises admixing into said lubricating composition an extreme pressure, anti-wear enhancing amount of an ashless and metals-free additive having the formula: ##STR7## wherein R 1 and R 2 are independently organic radicals or hydrogen, provided that both R 1 and R 2 are not simultaneously hydrogen, and further provided that the total number of carbon atoms in R 1 and R 2 is between 8 and 40, R 3 and R 4 are independently organic radicals, bromine, chlorine or hydrogen, provided that at least one of R 3 and R 4 is an organic radical, and further provided that the total number of carbon atoms in R 3 and R 4 is between 1 and 20, and R 5 is selected from the group consisting of hydrogen and organic radicals, said additive being soluble in 450 neutral oil at a concentration of at least 2.25 weight percent.
Claim 20
Dependent Claim
85 words
A lubricating composition comprising an oleaginous composition and an extreme pressure anti-wear enhancing amount of the reaction product of (1) 2-mercaptobenzothiazol, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic aldehydes and ketones having between 2 and 20 carbon atoms, and (3) a nitrogen-containing compound selected from the group consisting of primary and secondary amines having between 8 and 40 carbon atoms, said reaction product being soluble in 450 neutral oil at a concentration of at least 2.25 weight percent.
Claim 21
Dependent Claim
85 words
A lubricating composition comprising an oleaginous composition and an extreme pressure anti-wear enhancing amount of the reaction product of (1) 2-mercaptobenzothiazol, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic aldehydes and ketones having between 2 and 20 carbon atoms, and (3) a nitrogen-containing compound selected from the group consisting of primary and secondary amines having between 8 and 40 carbon atoms, said reaction product being soluble in 450 neutral oil at a concentration of at least 2.25 weight percent.
Claim 22
Dependent Claim
19 words
The composition of claim 17 wherein the 2-mercaptobenzothiazole, carbonyl-containing compound and amine are reacted in a 1:1:1 molar ratio.
Claim 23
Dependent Claim
27 words
The composition of claim 17 wherein the carbonyl-containing compound has one or more substituents selected from the group consisting of alkoxy, hydroxy, mercapto, nitrogen, and halogen groups.
Claim 24
Dependent Claim
33 words
The composition of claim 18 wherein said amine is a secondary amine selected from the group consisting of dihexyl amine, dioctyl amine, ditallow amine, dinonyl amine, didodecyl amine, dihexadecyl amine and dicyclohexyl amine.
Claim 25
Dependent Claim
192 words
A lubricating composition comprising an oleaginous material and an ashless and metals-free, extreme pressure, anti-wear additive of the formula: ##STR8## wherein: R 1 and R 2 are the same or different substituents selected from the group consisting of hydrogen and metals-free, substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the class consisting of oxygen, sulfur, and nitrogen atoms provided that R 1 and R 2 have a total of between about 8 and about 40 carbon atoms and are not both hydrogen; R 3 and R 4 are the same or different substituents selected from the group consisting of hydrogen and metal-free, substituted or unsubstituted alkyl, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, arylalkenyl, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the group consisting of oxygen, sulfur and nitrogen atoms provided that R 3 and R 4 have a total of between about 8 and 20 carbon atoms and are not both hydrogen; and R 5 is hydrogen or one or more organic substituents located on the benzene ring.
Claim 26
Dependent Claim
192 words
A lubricating composition comprising an oleaginous material and an ashless and metals-free, extreme pressure, anti-wear additive of the formula: ##STR8## wherein: R 1 and R 2 are the same or different substituents selected from the group consisting of hydrogen and metals-free, substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkynyloxy, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the class consisting of oxygen, sulfur, and nitrogen atoms provided that R 1 and R 2 have a total of between about 8 and about 40 carbon atoms and are not both hydrogen; R 3 and R 4 are the same or different substituents selected from the group consisting of hydrogen and metal-free, substituted or unsubstituted alkyl, aryl, arylalkyl, alkyloxy, aryloxy, arylalkyloxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, arylalkenyl, and cyclic hydrocarbon radicals, and heteroatom-substituted hydrocarbyl radicals wherein the heteroatoms are selected from the group consisting of oxygen, sulfur and nitrogen atoms provided that R 3 and R 4 have a total of between about 8 and 20 carbon atoms and are not both hydrogen; and R 5 is hydrogen or one or more organic substituents located on the benzene ring.
Claim 27
Dependent Claim
59 words
A lubricating composition comprising an oleaginous material and an ashless and metals-free, extreme pressure, anti-wear additive, said additive being a reaction product of (1) 2-mercaptobenzothiazole, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic adehydes and ketones having 2 to 20 carbon atoms, and (3) a nitrogen-containing compound comprising a primary or secondary amine.
Claim 28
Dependent Claim
59 words
A lubricating composition comprising an oleaginous material and an ashless and metals-free, extreme pressure, anti-wear additive, said additive being a reaction product of (1) 2-mercaptobenzothiazole, (2) a carbonyl-containing compound selected from the group consisting of aliphatic, aromatic or alicyclic adehydes and ketones having 2 to 20 carbon atoms, and (3) a nitrogen-containing compound comprising a primary or secondary amine.
Claim 29
Dependent Claim
30 words
The lubricating composition of claim 22 wherein the amine is an aliphatic or cycloaliphatic amine and wherein the 2-mercaptobenzothiazole, carbonyl-containing compound and amine are reacted in a 1:1:1 molar ratio.
Claim 30
Dependent Claim
28 words
The lubricating composition of claim 22 wherein the carbonyl-containing compound has one or more substituents selected from the group consisting of alkoxy, hydroxy, mercapto, nitro and halogen groups.
Claim 31
Dependent Claim
40 words
The lubricating composition of claim 22 wherein the carbonyl-containing compound is an aldehyde selected from the group consisting of phosgene, acetaldehyde, benzaldehyde, 2-ethylhexyl aldehyde, butyraldehyde, capryl aldehyde, acryl aldehyde, croton aldehyde, vinyl acetaldehyde, phenyl acetaldehyde, nitro benzaldehyde, furfural and chloral.
Claim 32
Dependent Claim
34 words
The lubricating composition of claim 22 wherein the carbonyl-containing compound is a ketone selected from the group consisting of acetone, methylethyl ketone, methylhexyl ketone, dihexyl ketone, dioctyl ketone, dinonyl ketone and di decyl ketone.
Claim 33
Dependent Claim
18 words
The lubricating composition of claim 23 wherein the carbonyl-containing compound contains between 2 and about 10 carbon atoms.
Claim 34
Dependent Claim
18 words
The lubricating composition of claim 22 wherein the amine contains between about 8 and about 40 carbon atoms.
Claim 35
Dependent Claim
37 words
The lubricating composition of claim 22 wherein the amine is selected from the group consisting of dihexyl amine, dioctyl amine, ditallow amine, dinonyl amine, didodecyl amine, dihexadecyl amine, hexadecyl amine, octadecyl amine, dicyclohexyl amine and N-methyl-n-octadecyl amine.
Claim 36
Dependent Claim
25 words
The lubricating composition of claim 22 wherein the amine is a dialkyl or dicycloalkyl secondary amine containing between about 8 and about 40 carbon atoms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-08-16 | 1992-02-15 | 1992-08-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-08-16 | 1996-02-15 | 1996-08-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-08-16 | 2000-02-15 | 2000-08-16 | $7700.00 | Window Closed / Lapsed |