US4524005A
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US
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Borated dihydrocarbylenetriamine amides and lubricant and fuel compositions containing same
Assignee: Mobil Oil AS
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Filing: 1984-02-01
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Granted: 1985-06-18
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Expires: 2004-02-01
Abstract
Abstract Borated hydrocarbylenetriamine amides can be made by borating the appropriate reaction product of a triamine and an organic monocarboxylic acid. They demonstrate friction reducing and/or fuel consumption reducing properties when formulated into lubricants, particularly lubricating oils, and fuels.
Inventors
- 👤 Andrew G. Horodysky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:41
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/08; C07; C07F; C07F5/00; C07F5/02; C07F5/04; C10L1/00; C10L1/10; C10L1/14; C10L1/30; C10L1/301; C10L1/303; C10M; C10M125/00; C10M125/26; C10M129/00; C10M129/02; C10M129/26; C10M129/28; C10M133/00; C10M133/02; C10M133/04; C10M133/06; C10M133/16; C10M139/00; C10M159/00; C10M159/12; C10M2201/00; C10M2201/087; C10M2201/10; C10M2201/102; C10M2201/105; C10M2207/00; C10M2207/10; C10M2207/12; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/24; C10M2215/26; C10M2217/00; C10M2217/04; C10M2217/046; C10M2217/06; C10M2227/00; C10M2227/06; C10M2227/061; C10M2227/062; C10M2227/063; C10M2227/065; C10M2227/066; C10N; C10N2040/00; C10N2040/25; C10N2040/251; C10N2040/255; C10N2040/28
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
192 words
A product of reaction made by (1) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, (2) followed by reacting the product of (1) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 95% of the available amino groups and the amount of boron compound reacted with the product from reaction (1) being in excess of the remaining amount required to react with the amino groups.
Claim 2
Dependent Claim
192 words
A product of reaction made by (1) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, (2) followed by reacting the product of (1) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 95% of the available amino groups and the amount of boron compound reacted with the product from reaction (1) being in excess of the remaining amount required to react with the amino groups.
Claim 3
Dependent Claim
25 words
The product of claim 1 wherein R is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl or cycloalkyl, and wherein at least one R is not hydrogen.
Claim 4
Dependent Claim
19 words
The product of claim 1 wherein R I is an ethylene group, a propylene group or a butylene group.
Claim 5
Dependent Claim
21 words
The product of claim 1 wherein R 2 and R 3 individually are a C 1 to C 4 hydrocarbyl group.
Claim 6
Dependent Claim
17 words
The product of claim 4 wherein the hydrocarbyl group is a methyl, ethyl, propyl or butyl group.
Claim 7
Dependent Claim
90 words
The product of claim 1 wherein the amine is N-oleyl diethylenetriamine, N-tallow diethylenetriamine, N-hydrogenated tallow diethylenetriamine, N-soya diethylenetriamine, N-coco diethylenetriamine, N-decyl diethylenetriamine, N-dodecyl diethylenetriamine, N-tetradecyl diethylenetriamine, N-octadecyl diethylenetriamine, N-eicosyl diethylenetriamine, N-triacontyl diethylenetriamine, N-oleyl dipropylenetriamine, N-tallow dipropylenetriamine, N-hydrogenated tallow dipropylenetriamine, N-soya dipropylenetriamine, N-coco dipropylenetriamine, N-decyl dipropylenetriamine, N-dodecyl dipropylenetriamine, N-tetradecyl dipropylenedtriamine, N-octadecyl dipropylenetriamine, N-eicosyl dipropylenetriamine, N-triacontyl dipropylenetriamine, the corresponding N--C 10 to C 30 hydrocarbyl dibutylenetriamine members, mixed N--C 10 to C 30 hydrocarbyl ethylenepropylenetriamine, mixed N--C 10 to C 30 hydrocarbyl ethylenebutylenetriamine or mixed N--C 10 to C 30 hydrocarbyl propylenebutylenetriamine.
Claim 8
Dependent Claim
20 words
The product of claim 5 wherein the acid is formic acid, acetic acid, propionic acid, butyric acid or mixtures thereof.
Claim 9
Dependent Claim
47 words
The product of claim 1 wherein the boron compound is a metaborate, boric oxide, boric acid, mono-, di- or trimethyl borate, mono-, di- or triethyl borate, mono-, di- or tripropyl borate, mono-, di- or tributyl borate, mono-, di- or triamyl borate or mono-, di- or trihexyl borate.
Claim 10
Dependent Claim
12 words
The product of claim 8 wherein the boron compound is boric acid.
Claim 11
Dependent Claim
23 words
The product of claim 1 wherein the amine is N-tallow-dipropylenetriamine, the boron compound is boric acid and the carboxylic acid is formic acid.
Claim 12
Dependent Claim
210 words
A lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a product of reaction made by (1) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, followed by reacting the product of (1) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 95% of the available amino groups and the amount of boron compound reacted with the product from reaction (1) being in excess of the remaining amount required to react with the amino groups.
Claim 13
Dependent Claim
210 words
A lubricant composition comprising a major amount of a lubricating oil or grease therefrom and an antifriction amount of a product of reaction made by (1) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, followed by reacting the product of (1) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 95% of the available amino groups and the amount of boron compound reacted with the product from reaction (1) being in excess of the remaining amount required to react with the amino groups.
Claim 14
Dependent Claim
25 words
The composition of claim 11 wherein R is hydrogen, alkyl, alkenyl, aryl, alkaryl, aralkyl or cycloalkyl, and wherein at least one R is not hydrogen.
Claim 15
Dependent Claim
19 words
The composition of claim 11 wherein R I is an ethylene group, a propylene group or a butylene group.
Claim 16
Dependent Claim
21 words
The composition of claim 11 wherein R 2 and R 3 are individually a C 1 to C 4 hydrocarbyl group.
Claim 17
Dependent Claim
17 words
The composition of claim 14 wherein the hydrocarbyl group is a methyl, ethyl, propyl or butyl group.
Claim 18
Dependent Claim
90 words
The composition of claim 11 wherein the amine is N-oleyl diethylenetriamine, N-tallow diethylenetriamine, N-hydrogenated tallow diethylenetriamine, N-soya diethylenetriamine, N-coco diethylenetriamine, N-decyl diethylenetriamine, N-dodecyl diethylenetriamine, N-tetradecyl diethylenetriamine, N-octadecyl diethylenetriamine, N-eicosyl diethylenetriamine, N-triacontyl diethylenetriamine, N-oleyl dipropylenetriamine, N-tallow dipropylenetriamine, N-hydrogenated tallow dipropylenetriamine, N-soya dipropylenetriamine, N-coco dipropylenetriamine, N-decyl dipropylenetriamine, N-dodecyl dipropylenetriamine, N-tetradecyl dipropylenedtriamine, N-octadecyl dipropylenetriamine, N-eicosyl dipropylenetriamine, N-triacontyl dipropylenetriamine, the corresponding N--C 10 to C 30 hydrocarbyl dibutylenetriamine members, mixed N--C 10 to C 30 hydrocarbyl ethylenepropylenetriamine, mixed N--C 10 to C 30 hydrocarbyl ethylenebutylenetriamine or mixed N--C 10 to C 30 hydrocarbyl propylenebutylenetriamine.
Claim 19
Dependent Claim
20 words
The composition of claim 15 wherein the acid is formic acid, acetic acid, propionic acid, butyric acid or mixtures thereof.
Claim 20
Dependent Claim
47 words
The composition of claim 11 wherein the boron compound is a metaborate, boric oxide, boric acid, mono-, di- or trimethyl borate, mono-, di- or triethyl borate, mono-, di- or tripropyl borate, mono-, di- or tributyl borate, mono-, di- or triamyl borate or mono-, di- or trihexyl borate.
Claim 21
Dependent Claim
12 words
The composition of claim 18 wherein the boron compound is boric acid.
Claim 22
Dependent Claim
23 words
The composition of claim 11 wherein the amine is N-tallow-dipropylenetriamine, the boron compound is boric acid and the carboxylic acid is formic acid.
Claim 23
Dependent Claim
39 words
The composition of claim 11 wherein the lubricant is (1) a mineral oil, (2) a synthetic oil or a mixture of synthetic oils, (3) a mixture of (1) and (2) and (4) a grease from (1), (2) or (3).
Claim 24
Dependent Claim
12 words
The composition of claim 21 wherein the lubricant is a mineral oil.
Claim 25
Dependent Claim
17 words
The composition of claim 21 wherein the lubricant is a synthetic oil or mixture of synthetic oils.
Claim 26
Dependent Claim
15 words
The composition of claim 21 wherein the lubricant is a mixture of (1) and (2).
Claim 27
Dependent Claim
11 words
The composition of claim 21 wherein the lubricant is said grease.
Claim 28
Independent Claim
226 words
A method of reducing fuel consumption in an internal combustion engine comprising lubricating said engine with a lubricating oil composition comprising a major proportion of a lubricating oil and a fuel consumption reducing amount of a product of reaction made by (A) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, (B) and reacting the product of (A) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 90% of the available amino groups and the amount of boron compound reacted with the product from reaction (A) being in excess of the remaining amount required to react with the amino groups.
Claim 29
Independent Claim
226 words
A method of reducing fuel consumption in an internal combustion engine comprising lubricating said engine with a lubricating oil composition comprising a major proportion of a lubricating oil and a fuel consumption reducing amount of a product of reaction made by (A) reacting an amine or a mixture of amines of the formula R--NH--R.sup.I --NH--R.sup.I --NHR wherein R is hydrogen or a C 10 to C 30 hydrocarbyl group, at least one R being the latter, and R I is the same or different C 2 to C 4 hydrocarbylene group with a carboxylic acid or ester of the formula R.sup.2 COOR.sup.3 wherein R 2 and R 3 are individually hydrogen or a C 1 to C 4 hydrocarbyl group, (B) and reacting the product of (A) with a boron compound selected from the group consisting of boric oxide, a metaborate, a compound of the formula (RO).sub.x B(OH).sub.y wherein R is a C 1 to C 6 alkyl group and x and y are 0 to 3, their sum being 3, and mixtures thereof, the amount of acid or ester reacted with the amine being sufficient to react from about 5% to about 90% of the available amino groups and the amount of boron compound reacted with the product from reaction (A) being in excess of the remaining amount required to react with the amino groups.
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) | 1988-06-17 | 1988-12-17 | 1989-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-17 | 1992-12-17 | 1993-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-17 | 1996-12-17 | 1997-06-18 | $7700.00 | Window Closed / Lapsed |