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US4507216A
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US
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Hindered phenyl esters of cyclic borates and lubricants containing same
Assignee: Mobil Oil AS
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Filing: 1983-03-14
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Granted: 1985-03-26
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Expires: 2003-03-14
Abstract
Abstract New reaction products obtained by reacting (1) a hindered phenol, (2) a borating agent and (3) a hydrocarbyl carboxylate are described. The preferred reaction sequence involves, first, the reaction of (1) and (2), then reacting the product obtained with the hydrocarbyl carboxylate. Also described are lubricant or liquid fuel compositions containing a major proportion of lubricant or fuel and an antifriction, anticorrosion or fuel reducing amount of the reaction product of this invention and a method of reducing fuel consumption in an internal combustion engine by lubricating the engine therewith.
Inventors
- 👤 Milton Braid
- 👤 Andrew G. Horodysky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 06:44
CPC Classifications
C; C10; C10M; C10M139/00; C10M2227/00; C10M2227/06; C10M2227/061; C10M2227/062; C10N; C10N2040/00; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
138 words
A reaction product prepared by reacting (1) a hindered phenol of the formula ##STR3## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y where R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 2
Dependent Claim
138 words
A reaction product prepared by reacting (1) a hindered phenol of the formula ##STR3## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y where R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 3
Dependent Claim
13 words
The product of claim 1 wherein said alkyl groups are tertiary alkyl groups.
Claim 4
Dependent Claim
23 words
The product of claim 1 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 5
Dependent Claim
24 words
The product of claim 1 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the carboxylate ester is glycerol monooleate.
Claim 6
Dependent Claim
169 words
A lubricant or liquid fuel composition comprising a major amount of a lubricating oil or grease therefrom or of a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR4## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y were R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 7
Dependent Claim
169 words
A lubricant or liquid fuel composition comprising a major amount of a lubricating oil or grease therefrom or of a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR4## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y were R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 8
Dependent Claim
13 words
The composition of claim 5 wherein said alkyl groups are tertiary alkyl groups.
Claim 9
Dependent Claim
23 words
The composition of claim 5 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 10
Dependent Claim
24 words
The composition of claim 5 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compond is boric acid and the carboxylate ester is glycerol monooleate.
Claim 11
Dependent Claim
39 words
The composition of claim 5 wherein said lubricant is (1) a mineral lubricating oil, (2) a synthetic lubricating oil or mixtures thereof, (3) mixtures of (1) and (2) and (4) a grease from any of (1), (2) and (3).
Claim 12
Dependent Claim
13 words
The composition of claim 9 wherein the lubricating oil is a mineral oil.
Claim 13
Dependent Claim
13 words
The composition of claim 9 wherein the lubricating oil is a synthetic oil.
Claim 14
Dependent Claim
16 words
The composition of claim 9 wherein the synthetic lubricating oil is a mixture of synthetic oils.
Claim 15
Dependent Claim
25 words
The composition of claim 9 wherein the lubricating oil is a mixture of (1) synthetic oil, or mixtures of synthetic oils, and (2) mineral oil.
Claim 16
Dependent Claim
11 words
The composition of claim 9 wherein the lubricant is a grease.
Claim 17
Dependent Claim
21 words
The composition of claim 5 wherein the liquid fuel is a liquid hydrocarbon or a liquid alcohol fuel, or mixtures thereof.
Claim 18
Independent Claim
183 words
A method of reducing fuel consumption in an internal combustion engine which comprises lubricating and/or fueling said engine with a composition comprising a major amount of a lubricating oil or grease therefrom or a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR5## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y where R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 19
Independent Claim
183 words
A method of reducing fuel consumption in an internal combustion engine which comprises lubricating and/or fueling said engine with a composition comprising a major amount of a lubricating oil or grease therefrom or a liquid fuel and an antifriction, antioxidant or fuel consumption reducing amount of reaction product prepared by reacting (1) a hindered phenol of the formula ##STR5## wherein R 1 is a C 1 to C 30 hydrocarbyl group and R 2 and R 3 are the same or different alkyl groups containing 4 to 18 carbon atoms, (2) a boron compound of the formula (RO).sub.p (BO.sub.2).sub.q Z.sub.r Y where R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p and r are 0 to 2 and q is 1 to 3 and (3) a carboxylate ester of the formula R.sup.4 (OCOR.sup.5).sub.n (OH).sub.t wherein R 4 is a hydrocarbyl group containing 3 to 6 carbon atoms, R 5 is a hydrocarbyl group containing 6 to 25 carbon atoms, n is 1 to 3 and t is 2 or 3.
Claim 20
Dependent Claim
13 words
The method of claim 16 wherein said alkyl groups are tertiary alkyl groups.
Claim 21
Dependent Claim
23 words
The method of claim 16 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 22
Dependent Claim
24 words
The method of claim 16 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the carboxylate ester is glycerol monooleate.
Claim 23
Dependent Claim
54 words
The method of claim 16 wherein said lubricant is (1) a mineral lubricating oil, (2) a synthetic lubricating oil or mixtures thereof, (3) mixtures of (1) and (2) and (4) a grease from any of (1), (2) and (3) and the liquid fuel is a liquid hydrocarbon a liquid alcohol fuel or mixtures thereof.
Claim 24
Dependent Claim
28 words
The composition of claim 5 containing additionally one or more additives selected from the group consisting of metal phenates, metal sulfonates, zinc phosphorodithioates, polymeric detergents and silicone defoamants.
Claim 25
Dependent Claim
24 words
The product of claim 1 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate.
Claim 26
Dependent Claim
24 words
The composition of claim 5 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate.
Claim 27
Dependent Claim
24 words
The method of claim 16 wherein the hindered phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is tributyl borate and the carboxylate ester is glycerol monooleate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-03-25 | 1988-09-24 | 1989-03-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-25 | 1992-09-24 | 1993-03-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-25 | 1996-09-24 | 1997-03-26 | $7700.00 | Window Closed / Lapsed |