US4474670A
Expired / Lapsed
US
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Hindered phenyl esters of cyclic borates and lubricants containing same
Assignee: Mobil Oil AS
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Filing: 1983-04-04
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Granted: 1984-10-02
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Expires: 2003-04-04
Abstract
Abstract New reaction products obtained by reacting (1) a hindered phenol, (2) a boron compound and (3) an amine together are described. Preferred reaction sequences are: (a) (2)+(1), then this product with (3); and (b) (2)+(3), then this product with (1). Also described are lubricant compositions containing the reaction products and a method of reducing fuel consumption in an internal combustion engine by lubricating the engine with a lubricant containing the reaction product.
Inventors
- 👤 Milton Braid
- 👤 Andrew G. Horodysky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 02:36
CPC Classifications
C; C10; C10M; C10M139/00; C07; C07F; C07F5/00; C07F5/02; C07F5/04; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/30; C10L1/301; C10L1/303; C10M137/00; C10M137/02; C10M137/04; C10M137/10; C10M141/00; C10M141/12; C10M2227/00; C10M2227/06; C10M2227/061; C10M2227/062; C10N; C10N2050/00; C10N2050/10
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
183 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 2
Dependent Claim
183 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
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
21 words
The product of claim 1 wherein the phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the amine is bis(2-hydroxyethyl)oleylamine.
Claim 6
Dependent Claim
202 words
A lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 7
Dependent Claim
202 words
A lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
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
21 words
The composition of claim 5 wherein the phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the amine is bis(2-hydroxyethyl)oleylamine.
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 11 wherein the synthetic lubricating oil is a mixture of synthetic oils.
Claim 15
Dependent Claim
28 words
The composition of claim 9 wherein the lubricating oil is a mixture of (1) a synthetic oil, or a mixture of synthetic oils and (2) a mineral oil.
Claim 16
Dependent Claim
11 words
The composition of claim 9 wherein the lubricant is a grease.
Claim 17
Independent Claim
218 words
A method of reducing fuel consumption in an internal combustion engine which comprises lubricating said engine with a lubricant composition comprising a major amount of a lubricating oil and a fuel consumption reducing amount of a 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 18
Independent Claim
218 words
A method of reducing fuel consumption in an internal combustion engine which comprises lubricating said engine with a lubricant composition comprising a major amount of a lubricating oil and a fuel consumption reducing amount of a 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 19
Dependent Claim
13 words
The method of claim 15 wherein said alkyl groups are tertiary alkyl groups.
Claim 20
Dependent Claim
23 words
The method of claim 15 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 21
Dependent Claim
21 words
The method of claim 15 wherein the phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the amine is bis(2-hydroxyethyl)oleylamine.
Claim 22
Dependent Claim
36 words
The method of claim 15 wherein said lubricant is selected from the group consisting of (1) a mineral lubricating oil, (2) a synthetic lubricating oil, mixtures of synthetic oils and (3) mixtures of (1) and (2).
Claim 23
Independent Claim
217 words
A method of hardening lubricated contacting metal surfaces which comprises lubricating said metal surfaces with a lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a reaction product prepared by reacting (1) a hindered phenol of the formula ##STR6## 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 24
Independent Claim
217 words
A method of hardening lubricated contacting metal surfaces which comprises lubricating said metal surfaces with a lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a reaction product prepared by reacting (1) a hindered phenol of the formula ##STR6## 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 YnZr wherein R, Y and Z are selected from the group consisting of hydrogen and a C 1 to C 6 alkyl group, p, n and r are 0 to 2 and q is 1 to 3 and (3) an amine of the formula R.sup.4 N(R.sup.5 OH).sub.2 wherein R 4 is a hydrocarbyl group containing 4 to 30 carbon atoms and R 5 is an alkylene or substituted alkylene group containing 1 to 12 carbon atoms, the reaction being carried out at from about 75° C. to about 250° C. and with proportions of reactants to give a phenol:boron compound ratio of from about 0.1:1 to abut 1:15 and from about 1 to about 2 mole equivalents of amine based on each mole of the phenol:boron compound moiety formed.
Claim 25
Dependent Claim
13 words
The method of claim 20 wherein said alkyl groups are tertiary alkyl groups.
Claim 26
Dependent Claim
23 words
The method of claim 20 wherein said hydrocarbyl groups are selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, aralkyl and alkaryl.
Claim 27
Dependent Claim
21 words
The method of claim 20 wherein the phenol is 2,6-di-tert-butyl-4-methylphenol, the boron compound is boric acid and the amine is bis(2-hydroxyethyl)oleylamine.
Claim 28
Dependent Claim
36 words
The method of claim 20 wherein said lubricant is selected from the group consisting of (1) a mineral lubricating oil, (2) a synthetic lubricating oil, mixtures of synthetic oils and (3) mixtures of (1) and (2).
Claim 29
Dependent Claim
24 words
The composition of claim 5 containing additionally one or more additives selected from the group consisting of metal sulfonates, metal phenates and zinc phosphorodithioates.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1987-10-02 | 1988-04-02 | 1988-10-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-02 | 1992-04-02 | 1992-10-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-02 | 1996-04-02 | 1996-10-02 | $7700.00 | Window Closed / Lapsed |