US4486321A
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Friction reducing additives and lubricating oil compositions containing same
Assignee: Mobil Oil AS
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Filing: 1983-01-10
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Granted: 1984-12-04
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Expires: 2003-01-10
Abstract
Abstract New compounds made by first reacting an amine, an aldehyde and a mercaptan and reacting the product thus obtained with a boron compound are provided. The invention also provides lubricant and liquid fuel compositions containing such compounds.
Inventors
- 👤 Andrew G. Horodysky
- 👤 Joan M. Kaminski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:24
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/08; C07; C07C; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07F; C07F5/00; C07F5/02; C07F5/022; C10L1/00; C10L1/10; C10L1/14; C10L1/24; C10L1/2493; C10M; C10M159/00; C10M159/12; C10M159/16; C10M2207/00; C10M2207/08; C10M2215/00; C10M2215/02; C10M2215/04; C10M2219/00; C10M2219/08; C10M2219/082; C10M2227/00; C10M2227/06; C10M2227/061; C10M2227/062; C10M2227/063; C10M2227/065; C10M2227/066
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
79 words
A reaction product obtained by reacting a hydrocarbylamine having 10 to 30 carbon atoms with a mercaptan and an aldehyde, the reaction taking place at from about 80° to about 160° C. using ratios of amine:aldehyde:mercaptan of from about 1:1:0.5 to abut 1:1:1 and (2) reacting the resulting product at from about 90° C. to about 150° C. with a sufficient amount of boron compound to give from about 0.1% to about 10% of boron in the final product.
Claim 2
Dependent Claim
79 words
A reaction product obtained by reacting a hydrocarbylamine having 10 to 30 carbon atoms with a mercaptan and an aldehyde, the reaction taking place at from about 80° to about 160° C. using ratios of amine:aldehyde:mercaptan of from about 1:1:0.5 to abut 1:1:1 and (2) reacting the resulting product at from about 90° C. to about 150° C. with a sufficient amount of boron compound to give from about 0.1% to about 10% of boron in the final product.
Claim 3
Dependent Claim
25 words
The product of claim 1 wherein the amine is selected from the group consisting of cocoamine, decylamine, dodecylamine, tetradecylamine, oleylamine, isostearylamine, myristylamine, palmitylamine and stearylamine.
Claim 4
Dependent Claim
44 words
The product of claim 1 wherein the amine has the formula: RNH(R.sup.1 NH).sub.x H wherein R is hydrogen or a C 1 to C 20 hydrocarbyl group, R 1 is a C 2 to C 5 alkylene group and x is 1 to 10.
Claim 5
Dependent Claim
20 words
The product of claim 3 wherein the amine is ethylenediamine, N-oleyl-ethylenediamine, N-oleyl-propylenediamine, N-coco-triethylenetetramine, N-oleyl-1,3-propylenediamine, N-coco-1,3-propylenediamine, N-tallow-1,3-propylenediamine, N-isomerictridecyl-1,3-propylenediamine, diethylenetriamine or tetraethylenepentamine.
Claim 6
Dependent Claim
27 words
The product of claim 1 wherein the aldehyde has the formula: R.sup.2 CHO wherein R 2 is hydrogen or a C 1 to C 8 hydrocarbyl group.
Claim 7
Dependent Claim
16 words
The product of claim 5 wherein the hydrocarbyl group is alkyl, alkenyl, cycloalkyl, alkaryl or aralkyl.
Claim 8
Dependent Claim
14 words
The product of claim 6 wherein the aldehyde is acetaldehyde, propionaldehyde, butyroaldehyde or 2-ethylhexylaldehyde.
Claim 9
Dependent Claim
25 words
The product of claim 1 wherein the mercaptan has the formula: R.sup.3 SH wherein R 3 is a C 8 to C 30 hydrocarbyl group.
Claim 10
Dependent Claim
13 words
The product of claim 8 wherein the hydrocarbyl group is an alkyl group.
Claim 11
Dependent Claim
26 words
The product of claim 8 wherein the mercaptan is n-dodecyl mercaptan, n-nonyl mercaptan, N-octyl mercaptan, n-decyl mercaptan, n-myristyl mercaptan, n-hexadecyl mercaptan, stearyl mercaptan or oleyl mercaptan.
Claim 12
Dependent Claim
52 words
The product of claim 1 wherein the boron compound is boric acid or a compound of the formula: (R.sup.4 O).sub.a B(OH).sub.b wherein R 4 is a C 1 to C 6 alkyl group, a is 0 to 3 and b is 0 to 3, the sum of a and b being 3.
Claim 13
Dependent Claim
26 words
The product of claim 1 wherein the amine is oleylamine, the aldehyde is formaldehyde, the mercaptan is dodecyl mercaptan and the boron compound is boric acid.
Claim 14
Dependent Claim
22 words
The product of claim 1 wherein the amine is oleylamine, the mercaptan is dodecyl mercaptan and the boron compound is boric acid.
Claim 15
Dependent Claim
100 words
A lubricant composition comprising a major proportion of a lubricating oil or grease therefrom and a friction reducing amount of a reaction product obtained by reacting a hydrocarbylamine having 10 to 30 carbon atoms with a mercaptan and an aldehyde, the reaction taking place at from about 80° to about 160° C. using molar ratios of amine:aldehyde:mercaptan of from about 1:1:0.5 to abut 1:1:1 and (2) reacting the resulting product of from about 90° C. to about 150° C. with a sufficient amount of boron compound to give from about 0.1% to about 10% of boron in the final product.
Claim 16
Dependent Claim
100 words
A lubricant composition comprising a major proportion of a lubricating oil or grease therefrom and a friction reducing amount of a reaction product obtained by reacting a hydrocarbylamine having 10 to 30 carbon atoms with a mercaptan and an aldehyde, the reaction taking place at from about 80° to about 160° C. using molar ratios of amine:aldehyde:mercaptan of from about 1:1:0.5 to abut 1:1:1 and (2) reacting the resulting product of from about 90° C. to about 150° C. with a sufficient amount of boron compound to give from about 0.1% to about 10% of boron in the final product.
Claim 17
Dependent Claim
25 words
The composition of claim 14 wherein the amine is selected from the group consisting of cocoamine, decylamine, dodecylamine, tetradecylamine, oleylamine, isostearylamine, myristylamine, palmitylamine and stearylamine.
Claim 18
Dependent Claim
44 words
The composition of claim 14 wherein the amine has the formula: RNH(R.sup.1 NH).sub.x H wherein R is hydrogen or a C 1 to C 20 hydrocarbyl group, R 1 is a C 2 to C 5 alkylene group and x is 1 to 10.
Claim 19
Dependent Claim
20 words
The composition of claim 16 wherein the amine is ethylenediamine, N-oleyl-ethylenediamine, N-oleyl-propylenediamine, N-coco-triethylenetetramine, N-oleyl-1,3-propylenediamine, N-coco-1,3-propylenediamine, N-tallow-1,3-propylenediamine, N-isomerictridecyl-1,3-propylenediamine, diethylenetriamine or tetraethylenepentamine.
Claim 20
Dependent Claim
27 words
The composition of claim 14 wherein the aldehyde has the formula: R.sup.2 CHO wherein R 2 is hydrogen or a C 1 to C 8 hydrocarbyl group.
Claim 21
Dependent Claim
16 words
The composition of claim 18 wherein the hydrocarbyl group is alkyl, alkenyl, cycloalkyl, alkaryl or aralkyl.
Claim 22
Dependent Claim
15 words
The composition of claim 18 wherein the aldehyde is formaldehyde, acetaldehyde, propionaldehyde, butyroaldehyde or 2-ethylhexylaldehyde.
Claim 23
Dependent Claim
25 words
The composition of claim 14 wherein the mercaptan has the formula: R.sup.3 SH wherein R 3 is a C 8 to C 30 hydrocarbyl group.
Claim 24
Dependent Claim
13 words
The composition of claim 21 wherein the hydrocarbyl group is an alkyl group.
Claim 25
Dependent Claim
26 words
The composition of claim 14 wherein the mercaptan is n-dodecyl mercaptan, n-nonyl mercaptan, N-octyl mercaptan, n-decyl mercaptan, n-myristyl mercaptan, n-hexadecyl mercaptan, stearyl mercaptan or oleyl mercaptan.
Claim 26
Dependent Claim
52 words
The composition of claim 14 wherein the boron compound is boric acid or a compound of the formula: (R.sup.4 O).sub.a B(OH).sub.b wherein R 4 is a C 1 to C 6 alkyl group, a is 0 to 3 and b is 0 to 3, the sum of a and b being 3.
Claim 27
Dependent Claim
26 words
The composition of claim 14 wherein the amine is oleylamine, the aldehyde is formaldehyde, the mercaptan is dodecyl mercaptan and the boron compound is boric acid.
Claim 28
Dependent Claim
26 words
The composition of claim 14 wherein the amine is cocoamine, the mercaptan is dodecyl mercaptan and the boron compound is boric acid, the aldehyde is formaldehyde.
Claim 29
Dependent Claim
36 words
The composition of claim 14 wherein the lubricant is (1) a mineral oil, (2) a synthetic oil or mixtures of synthetic oils, (3) mixtures of (1) and (2) or (4) a grease of any of these.
Claim 30
Dependent Claim
12 words
The composition of claim 2 wherein the lubricant is a mineral oil.
Claim 31
Dependent Claim
12 words
The composition of claim 27 wherein the lubricant is a synthetic oil.
Claim 32
Dependent Claim
16 words
The composition of claim 27 wherein the lubricant is a mixture of mineral and synthetic oils.
Claim 33
Dependent Claim
11 words
The composition of claim 27 wherein the lubricant is a grease.
References Cited (Backward Citations)
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US3224971A
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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) | 1987-12-04 | 1988-06-04 | 1988-12-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-04 | 1992-06-04 | 1992-12-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-04 | 1996-06-04 | 1996-12-04 | $7700.00 | Window Closed / Lapsed |