US4380498A
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Sulfurized, transesterified oil additives and their use in a lubricating oil and a fuel
Assignee: Vibrantz Corp
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Filing: 1981-08-10
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Granted: 1983-04-19
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Expires: 2001-08-10
Abstract
Abstract Improved lubricant additive compositions, derived from fatty oils, comprise triglycerides which have been transesterified with polybasic carboxylic acids prior to sulfurization. Such additive compositions possess improved solubility in oils and impart improved lubrication properties to both lubricant and fuel compositions.
Inventors
- 👤 Karl P. Kammann, Jr.
- 👤 Marvin J. Den Herder
- 👤 Terrence L. Wagner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:08
CPC Classifications
C; C07; C07C; C07C323/00; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/24; C10L1/2493; C10M; C10M135/00; C10M135/02; C10M135/06; C10M2219/00; C10M2219/02; C10M2219/024
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
30 words
A sulfurized, triglyceride additive composition comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 2
Dependent Claim
30 words
A sulfurized, triglyceride additive composition comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 3
Dependent Claim
24 words
The composition of claim 1 wherein the polybasic carboxylic acids comprise dibasic acids having from about 3 to about 36 carbon atoms per molecule.
Claim 4
Dependent Claim
21 words
The composition of claim 2 wherein the dibasic acids comprise unsaturated acids having from about 21 to about 36 carbon atoms.
Claim 5
Dependent Claim
14 words
The composition of claim 3 wherein the unsaturated dibasic acids comprise dimerized linoleic acid.
Claim 6
Dependent Claim
19 words
The composition of claim 3 wherein the unsaturated dibasic acids comprise the dimerized product of linoleic and acrylic acids.
Claim 7
Dependent Claim
29 words
The composition of claim 1 wherein the polybasic carboxylic acids comprise a mixture of dibasic and tribasic acids having from about 3 to about 54 carbon atoms per molecule.
Claim 8
Dependent Claim
25 words
The composition of claim 6 wherein the mixture of dibasic and tribasic acids comprises unsaturated acids having from about 21 to about 54 carbon atoms.
Claim 9
Dependent Claim
21 words
The composition of claim 7 wherein the mixture of unsaturated dibasic and tribasic acids comprises dimers and trimers of linoleic acid.
Claim 10
Dependent Claim
10 words
The composition of claim 1, additionally comprising a solubilization agent.
Claim 11
Dependent Claim
26 words
The composition of claim 9 wherein the solubilization agent is selected from the group consisting of triglycerides, olefins, esters of unsaturated carboxylic acids, and mixtures thereof.
Claim 12
Dependent Claim
12 words
The composition of claim 10 wherein the solubilization agent is a triglyceride.
Claim 13
Dependent Claim
12 words
The composition of claim 10 wherein the solubilization agent is an olefin.
Claim 14
Dependent Claim
22 words
The composition of claim 12 wherein the olefin contains from about 8 to about 20 carbon atoms, alone or in mixtures thereof.
Claim 15
Dependent Claim
17 words
The composition of claim 10 wherein the solubilization agent is an ester of an unsaturated carboxylic acid.
Claim 16
Dependent Claim
33 words
The composition of claim 9 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 70 wt. %, based on the sulfurized, transesterified triglyceride.
Claim 17
Dependent Claim
33 words
The composition of claim 15 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 55 wt. %, based on the sulfurized, transesterified triglyceride.
Claim 18
Dependent Claim
32 words
The composition of claim 1 wherein bound sulfur is present in an amount within the range from about 2 wt. % to about 10 wt. %, based on the sulfurized, transesterified triglyceride.
Claim 19
Dependent Claim
95 words
A process for preparing a sulfurized, transesterified triglyceride additive composition, comprising the steps of: (1) transesterifying one or more triglycerides with one or more organic polybasic acids, or esters thereof, to yield a transesterified triglyceride wherein the total acid component comprises from about 5 mole % to about 50 mole % polybasic carboxylic acids; and (2) sulfurizing the transesterified triglyceride product mixture of step 1 with elemental sulfur to incorporate bound sulfur in an amount within the range from about 2 wt. % to about 10 wt. %, based upon the transesterified triglyceride product mixture.
Claim 20
Dependent Claim
95 words
A process for preparing a sulfurized, transesterified triglyceride additive composition, comprising the steps of: (1) transesterifying one or more triglycerides with one or more organic polybasic acids, or esters thereof, to yield a transesterified triglyceride wherein the total acid component comprises from about 5 mole % to about 50 mole % polybasic carboxylic acids; and (2) sulfurizing the transesterified triglyceride product mixture of step 1 with elemental sulfur to incorporate bound sulfur in an amount within the range from about 2 wt. % to about 10 wt. %, based upon the transesterified triglyceride product mixture.
Claim 21
Dependent Claim
24 words
The process of claim 18, wherein said polybasic carboxylic acids comprise dibasic acids having from about 3 to about 36 carbon atoms per molecule.
Claim 22
Dependent Claim
21 words
The process of claim 19, wherein said dibasic acids comprise unsaturated acids having from about 21 to about 36 carbon atoms.
Claim 23
Dependent Claim
14 words
The process of claim 20, wherein said unsaturated dibasic acids comprise dimerized linoleic acid.
Claim 24
Dependent Claim
19 words
The process of claim 20, wherein said unsaturated dibasic acids comprise the dimerized product of linoleic and acrylic acids.
Claim 25
Dependent Claim
29 words
The process of claim 18, wherein said polybasic carboxylic acids comprise a mixture of dibasic and tribasic acids having from about 3 to about 54 carbon atoms per molecule.
Claim 26
Dependent Claim
25 words
The process of claim 23, wherein said mixture of dibasic and tribasic acids comprises unsaturated acids having from about 21 to about 54 carbon atoms.
Claim 27
Dependent Claim
21 words
The process of claim 24, wherein said mixture of unsaturated dibasic and tribasic acids comprises dimers and trimers of linoleic acid.
Claim 28
Dependent Claim
27 words
The process of claim 18, additionally comprising the step of esterifying free acids in the transesterification reaction product with an alcohol component prior to the sulfurization step.
Claim 29
Dependent Claim
17 words
The process of claim 26 wherein said alcohol component for esterification comprises branched chain aliphatic primary alcohols.
Claim 30
Dependent Claim
37 words
The process of claim 18, additionally comprising the step of blending said transesterification reaction product with a compound selected from the group consisting of triglycerides, esterified fatty acids, α-olefins and mixtures thereof, prior to the sulfurization step.
Claim 31
Dependent Claim
19 words
The process of claim 18, wherein said transesterification step is carried out in the presence of a transesterification catalyst.
Claim 32
Dependent Claim
37 words
The process of claim 18, wherein said transesterification catalyst is selected from the group consisting of tetrabutyl titanate, zinc acetate, sodium carbonate, sodium sulfate, stannous oxalate, p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, butylchlorotin dihydroxide, and phosphoric acid.
Claim 33
Dependent Claim
29 words
The process of claim 29, wherein said transesterification catalyst is present in an amount within the range from about 0.01 to about 1 wt. %, based on the triglycerides.
Claim 34
Dependent Claim
24 words
The process of claim 31, wherein said catalyst is present in an amount within the range from about 0.03 to about 0.5 wt. %.
Claim 35
Dependent Claim
11 words
The process of claim 30 wherein said catalyst is p-toluenesulfonic acid.
Claim 36
Dependent Claim
11 words
The process of claim 30, wherein said catalyst is methanesulfonic acid.
Claim 37
Dependent Claim
66 words
A lubricating oil composition, comprising: (1) a refined base oil, having lubricating oil viscosity and volatility properties; and (2) a minor amount, from about 0.05 to about 15 wt. % of the lubricating oil composition, of a sulfurized, triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 38
Dependent Claim
66 words
A lubricating oil composition, comprising: (1) a refined base oil, having lubricating oil viscosity and volatility properties; and (2) a minor amount, from about 0.05 to about 15 wt. % of the lubricating oil composition, of a sulfurized, triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 39
Dependent Claim
34 words
The lubricating oil composition of claim 35 wherein the sulfurized triglyceride additive composition is present in an amount within the range from about 0.5 to about 5 wt. % of the lubricating oil composition.
Claim 40
Dependent Claim
63 words
A fuel composition, comprising: (1) a blended base fuel, having suitable volatility and combustion properties; and (2) a minor amount, from about 0.0005 to about 0.1 wt. % of the fuel composition, of a sulfurized triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 41
Dependent Claim
63 words
A fuel composition, comprising: (1) a blended base fuel, having suitable volatility and combustion properties; and (2) a minor amount, from about 0.0005 to about 0.1 wt. % of the fuel composition, of a sulfurized triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride includes from about 5 to about 50 mole % polybasic carboxylic acids.
Claim 42
Dependent Claim
23 words
The fuel composition of claim 37 wherein the blended base fuel is a gasoline fuel, for use in a spark-ignition internal combustion engine.
Claim 43
Dependent Claim
23 words
The fuel composition of claim 37 wherein the blended base fuel is a diesel fuel, for use in a compression-ignition internal combustion engine.
Claim 44
Dependent Claim
22 words
The fuel composition of claim 37 wherein the blended base fuel is a heating oil, for use in an oil-fired burner assembly.
Claim 45
Dependent Claim
32 words
The fuel composition of claim 37 wherein the sulfurized triglyceride additive composition is present in an amount within the range from about 0.0015 to about 0.05 wt. % of the fuel composition.
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) | 1986-04-18 | 1986-10-18 | 1987-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-04-18 | 1990-10-18 | 1991-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-04-18 | 1994-10-18 | 1995-04-19 | $7700.00 | Window Closed / Lapsed |