Claims
- 1. A lubricant additive comprising a phosphite adduct of triglyceride meadowfoam oil, wherein the phosphite adduct is a mono-, di-, tri-, tetra-, penta-, or hexa-adduct of the reaction product of ##STR9## and triglyceride meadowfoam oil, wherein R is selected from the group consisting of H, C.sub.1-12 alkyl, C.sub.1-12 aryl, C.sub.1-12 alkaryl, C.sub.1-12 aralkyl, and cyclo C.sub.4-12 alkyl.
- 2. The lubricant additive of claim 1 wherein R is selected from the group consisting of C.sub.4-8 alkyl, C.sub.4-8 alkaryl, C.sub.4-8 aralkyl, and cyclo C.sub.4-8 alkyl.
- 3. The lubricant additive of claim 2 wherein R is n-butyl.
- 4. The lubricant additive of claim 1 wherein the phosphite adduct point of attachment to triglyceride meadowfoam oil is at a carbon-carbon double bond.
SUMMARY OF THE INVENTION
This application is a divisional of Ser. No. 221,061 filed on July 19, 1988, now U.S. Pat. No. 4,925,581.
1. Technical Field
The present invention relates to lubricant compositions and lubricant additives and to methods for producing lubricant additives with antifriction properties that contain meadowfoam oil and meadowfoam oil derivatives as lubricating agents. More specifically, this invention relates to wax esters of meadowfoam oil fatty acids, sulfurized meadowfoam oil triglycerides, sulfurized meadowfoam oil wax esters, meadowfoam oil triglycerides, phosphite adducts of meadowfoam oil triglycerides, and phosphite adducts of meadowfoam oil wax esters as lubricant additives in various combinations.
2. Background of the Invention
Meadowfoam (Limnanthes laba) is a herbaceous winter annual plant native to the Pacific Northwest region of the U.S. The common name "meadowfoam" was given because of the appearance of its solid canopy of creamy white flowers at full bloom. Meadowfoam is currently being grown commercially in Oregon's Willamette Valley.
Meadowfoam oil is a triglyceride oil that is extracted from meadowfoam seeds. Meadowfoam seeds are pear-shaped, consisting of a thin, brown, striated hull surrounding a relatively soft, light-colored dicotyledon kernel. The seeds, measuring about 2.times.3 mm, average about 150 to the gram. The kernels contribute about two-thirds of the total weight and contain essentially all of the triglyceride oil. Commercial meadowfoam seeds generally contain about 27% oil. The physical and chemical properties of meadowfoam oil are shown in FIG. 1.
Lubricants are widely used to reduce the friction between the surfaces of moving parts and thereby reduce the wear and prevent damage to the parts. Most lubricants are comprised principally of a base stock which is generally a relatively high molecular weight hydrocarbon. In applications where the amount of pressure applied to the moving part is quite high, lubricants which are comprised of only hydrocarbon base stock tend to fail and the contacting parts are damaged. It is well known to add materials (lubricant additives) to increase the high pressure performance of lubricants. These materials are generally called "extreme pressure additives." Examples of extreme pressure additives are sulfurized materials such as sulfurized sperm whale oil or sulfurized jojoba oil.
Meadowfoam oil is a triglyceride with approximately 95% of the falty acids being C.sub.20 and C.sub.22 fatty acids and primarily monoenoic (single unsaturation). Further, there is a lack of conjugation of even the dienoic fatty acids, as the double bonds are located far from each other. This amount of unsaturation provides for greater oxidative stability than is found in conjugated, unsaturated fatty acids. Meadowfoam oil is a triglyceride in which the .alpha.- and .alpha.'-positions are most often occupied by 5' monoenoic acids and the major fatty acids are: 5-eicosenoic, 11-eicosenoic, 5-docosenoic, 13-docosenoic, and 5,13-docosadienoic acids.
Wax esters can be sulfurized from natural wax esters, such as from jojoba oil, and from synthesized wax esters, such as from vegetable oil triglycerides and liberated fatty acids. Natural wax esters have produced formulated sulfurized products that provide effective lubricant additive compositions. However, the problems with the natural wax esters are availability and cost. The vegetable oils have to be transesterified from the free fatty acids to produce the wax esters. For practical applications, however, the vegetable oil triglycerides have the disadvantage that cost-adding conversion steps are necessary to form a wax ester for sulfurization, rather than a direct sulfurization of the triglyceride. These extra processing steps make vegetable oil wax esters relatively uneconomical as lubricant additives.
Princen et al., "Development of New Crops for Industrial Raw Materials," J. Amer. Oil Chemists Soc., 61:281-89, 1984, tried to sulfurize meadowfoam oil by sulfurizing the wax esters of the meadowfoam fatty acids. Princen et al. found that sulfurization of the unaltered triglyceride oil can react with sulfur under traditional sulfurization conditions to yield factice, a solid chemical rubber and an unacceptable lubricant additive. The first sulfurized wax ester of meadowfoam oil preparation in Princen et al. had good lubrication properties, but it corroded copper, foamed excessively, and thickened excessively under in-use conditions in a hot gear box. The second sulfurized wax ester of meadowfoam oil preparation in Princen et al. was made with different synthesis conditions, but the second preparation decreased copper corrosion and maintained lubricating properties but produced more foam and did not meet a thermal stability test. The third preparation in Princen et al. used wax esters from enriched monoene and diene acids. The diene wax ester (made from monoenoic fatty acids) resulted in increased wear scar but favorable other properties.
Wakim, U.S. Pat. No. 3,986,966 after demonstrating that sulfurization of triglycerides alone gave resinous products mostly insoluble in base oils, added nonwax methyl esters of a fatty acid of 18 to 22 carbon atoms which are monounsaturated to improve the solubility of the sulfurized triglycerides.
Hutchinson et al., U.S. Pat. No. 3,740,333 refers to sulfurized blends of lard oil and a saturated wax ester, the essential element of the wax ester being derived from a C.sub.10-16 saturated alcohol and a C.sub.18-22 unsaturated acid.
Kammann et al., "Sulfurized Vegetable Oil Products as Lubricant Additives," J. Amer. Oil Chemists Soc., 62:917-23, 1985, found that sulfurized vegetable triglyceride oils resulted in rubbery products, in some cases even at a 12% sulfur content. Kammann et al. tried using sulfurization with large amounts of methyl lardate, but obtained factice or near factice with meadowfoam oil. Kammann et al. was able to sulfurize only by adding 10% unsaturated oleic acid before sulfurization; however, the resulting product properties were undesirable as a lubricant additive.
There are many problems using a sulfurized meadowfoam oil. Therefore, there exists a need in the art to find lubricant additive compositions that can use the relatively abundant supplies of meadowfoam oil without resorting to the multiple processing steps of making wax esters of the fatty acids. There further exists a need in the, art to be able to sulfurize meadowfoam oil in the triglyceride state for use as a lubricant additive.
Briefly stated, the present invention encompasses lubricant additives comprising combinations of meadowfoam oil with at least one of sulfurized meadowfoam oil and a phosphite adduct of meadowfoam oil. The meadowfoam oil can be in the form of the native triglyceride or as a meadowfoam wax ester. The sulfurized meadowfoam oil comprises either a sulfurized mixture of the triglyceride form of meadowfoam oil with from about 25% to about 75% of a wax ester or sulfurized meadowfoam wax ester. The wax ester is jojoba oil or is derived from a C.sub.18-22 unsaturated acid and a C.sub.18-22 unsaturated alcohol. Preferably, the wax ester is a naturally occurring wax ester, such as jojoba oil, or the wax ester of meadowfoam oil. The phosphite adduct of meadowfoam oil can be a mono- through hexa-adduct of the triglyceride form of meadowfoam oil, or a mono- through tetra-adduct of the wax ester form of meadowfoam oil.
The phosphite adduct of meadowfoam oil is formed by the reaction of triglyceride meadowfoam oil or wax ester of meadowfoam oil and a compound of the formula: ##STR1## wherein R is H, C.sub.1-12 alkyl, C.sub.1-12 aryl, C.sub.1-12 alkaryl, C.sub.1-12 aralkyl, and cyclo C.sub.4-12 alkyl. Preferably, R is C.sub.4-8 alkyl, C.sub.4-8 alkaryl, C.sub.4-8 aralkyl, or cyclo C.sub.4-8 alkyl. Most preferably, R is n-butyl.
The present invention further comprises a lubricating composition consisting essentially of a lubricant base and a lubricant additive wherein the lubricant additive comprises a mixture of at least two ingredients from different classes of ingredients selected from the group consisting of three classes of ingredients:
wherein the first class of ingredients comprises a triglyceride meadowfoam oil, a wax ester of meadowfoam oil, and a combination thereof;
wherein the second class of ingredients comprises: a sulfurized meadowfoam oil wax ester; a sulfurized triglyceride meadowfoam oil within the range of from about 25% to about 75% meadowfoam oil, and from about 25% to about 75% of a wax ester; and a combination thereof; and
wherein the third class of ingredients comprises a phosphite adduct of triglyceride meadowfoam oil, a phosphite adduct of meadowfoam oil wax ester, and a combination thereof.
US Referenced Citations (4)
Divisions (1)
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221061 |
Jul 1988 |
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Patent Grant
5023312
