US4380499A
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Sulfurized fatty 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 sulfurized, transesterified triglycerides. 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
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 09:51
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
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
119 words
A sulfurized, triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 2
Dependent Claim
119 words
A sulfurized, triglyceride additive composition, comprising a sulfurized, transesterified triglyceride wherein the total acid component of the triglyceride comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 3
Dependent Claim
24 words
The sulfurized triglyceride additive composition of claim 1, wherein said mono-unsaturated fatty acids are present in an amount greater than about 35 mole %.
Claim 4
Dependent Claim
24 words
The sulfurized triglyceride additive composition of claim 1, wherein said poly-unsaturated fatty acids are present in an amount less than about 10 mole %.
Claim 5
Dependent Claim
25 words
The sulfurized triglyceride additive composition of claim 1, wherein said total saturated aliphatic acids are present in an amount greater than about 50 mole %.
Claim 6
Dependent Claim
29 words
The sulfurized triglyceride additive composition of claim 1, wherein said saturated acids having 6 to 14 carbon atoms are present in an amount greater than about 15 mole %.
Claim 7
Dependent Claim
29 words
The sulfurized triglyceride additive composition of claim 1, wherein said saturated acids having 6 to 16 carbon atoms are present in an amount greater than about 35 mole %.
Claim 8
Dependent Claim
13 words
The sulfurized triglyceride additive composition of claim 1, additionally comprising a solubilization agent.
Claim 9
Dependent Claim
29 words
The sulfurized triglyceride additive composition of claim 7 wherein the solubilization agent is selected from the group consisting of triglycerides, olefins, esters of unsaturated carboxylic acids, and mixtures thereof.
Claim 10
Dependent Claim
15 words
The sulfurized triglyceride additive composition of claim 8 wherein the solubilization agent is a triglyceride.
Claim 11
Dependent Claim
15 words
The sulfurized triglyceride additive composition of claim 8 wherein the solubilization agent is an olefin.
Claim 12
Dependent Claim
25 words
The sulfurized triglyceride additive composition of claim 10 wherein the olefin contains from about 8 to about 20 carbon atoms, alone or in mixtures thereof.
Claim 13
Dependent Claim
20 words
The sulfurized triglyceride additive composition of claim 8 wherein the solubilization agent is an ester of an unsaturated carboxylic acid.
Claim 14
Dependent Claim
35 words
The sulfurized triglyceride additive composition of claim 7 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 70 wt. % based on the transesterified triglyceride.
Claim 15
Dependent Claim
35 words
The sulfurized triglyceride additive composition of claim 13 wherein the solubilization agent is present in an amount within the range from about 5 wt. % to about 55 wt. %, based on the transesterified triglyceride.
Claim 16
Dependent Claim
34 words
The sulfurized triglyceride additive composition of claim 1 wherein bound sulfur is present in an amount within the range from about 4 wt. % to about 14 wt. %, based on the total product.
Claim 17
Independent Claim
182 words
A method for preparing a sulfurized, transesterified triglyceride additive composition, comprising the steps of: (1) transesterifying one or more triglycerides with one or more organic acids, or esters thereof, to yield a transesterified triglyceride wherein the total acid component comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of monounsaturated fatty acids; (b) less than about 15 mole % of polyunsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms; 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 4 wt. % to about 14 wt. %, based upon the transesterified triglyceride product mixture.
Claim 18
Independent Claim
182 words
A method for preparing a sulfurized, transesterified triglyceride additive composition, comprising the steps of: (1) transesterifying one or more triglycerides with one or more organic acids, or esters thereof, to yield a transesterified triglyceride wherein the total acid component comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of monounsaturated fatty acids; (b) less than about 15 mole % of polyunsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms; 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 4 wt. % to about 14 wt. %, based upon the transesterified triglyceride product mixture.
Claim 19
Dependent Claim
21 words
The method of claim 16, wherein said monounsaturated fatty acids are present in an amount greater than about 35 mole %.
Claim 20
Dependent Claim
21 words
The method of claim 16, wherein said polyunsaturated fatty acids are present in an amount less than about 10 mole %.
Claim 21
Dependent Claim
22 words
The method of claim 16, wherein said total saturated aliphatic acids are present in an amount greater than about 50 mole %.
Claim 22
Dependent Claim
27 words
The method of claim 16, additionally comprising the step of esterifying free acids in the tranesterification reaction product with an alcohol component prior to the sulfurization step.
Claim 23
Dependent Claim
17 words
The method of claim 20 wherein said alcohol component for esterification comprises branched chain aliphatic primary alcohols.
Claim 24
Dependent Claim
37 words
The method of claim 16, 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 25
Dependent Claim
19 words
The method of claim 16 wherein said transesterification step is carried out in the presence of a transesterification catalyst.
Claim 26
Dependent Claim
37 words
The method of claim 23 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 27
Dependent Claim
29 words
The method of claim 23 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 28
Dependent Claim
25 words
The method of claim 25 in which said catalyst is present in an amount within the range from about 0.03 to about 0.5 wt. %.
Claim 29
Dependent Claim
11 words
The method of claim 24 wherein said catalyst is p-toluenesulfonic acid.
Claim 30
Dependent Claim
11 words
The method of claim 24 wherein said catalyst is methanesulfonic acid.
Claim 31
Dependent Claim
155 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 comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 32
Dependent Claim
155 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 comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 33
Dependent Claim
34 words
The lubricating oil composition of claim 29 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 34
Dependent Claim
152 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 comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 35
Dependent Claim
152 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 comprises no less than about 35 mole % saturated aliphatic acids and no more than about 65 mole % unsaturated fatty acids, said total acid component being further characterized as comprising: (a) more than about 20 mole % of mono-unsaturated acids; (b) less than about 15 mole % of poly-unsaturated fatty acids; (c) more than about 20 mole % saturated aliphatic acids having 6 to 16 carbon atoms, including more than about 10 mole % saturated aliphatic acids having 6 to 14 carbon atoms; and (d) less than about 15 mole % saturated aliphatic acids having 18 or more carbon atoms.
Claim 36
Dependent Claim
23 words
The fuel composition of claim 31 wherein the blended base fuel is a gasoline fuel, for use in a spark-ignition internal combustion engine.
Claim 37
Dependent Claim
23 words
The fuel composition of claim 31 wherein the blended base fuel is a diesel fuel, for use in a compression-ignition internal combustion engine.
Claim 38
Dependent Claim
22 words
The fuel composition of claim 31 wherein the blended base fuel is a heating oil, for use in an oil-fired burner assembly.
Claim 39
Dependent Claim
32 words
The fuel composition of claim 31 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 |