Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Heterocyclic ring compound; a heterocyclic ring is one...
Reexamination Certificate
2001-11-30
2003-05-20
Johnson, Jerry D. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Heterocyclic ring compound; a heterocyclic ring is one...
Reexamination Certificate
active
06566311
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention is related to lubricants, especially lubricating oils, and, more particularly, to a class of ashless and non-phosphorus, non-sulfur-containing anti-wear, anti-fatigue, and extreme pressure additives derived from 1,3,4-oxadiazoles.
2. Description of Related Art
In developing lubricating oils, there have been many attempts to provide additives that impart anti-fatigue, anti-wear, and extreme pressure properties thereto. Zinc dialkyldithiophosphates (ZDDP) have been used in formulated oils as anti-wear additives for more than 50 years. However, zinc dialkyldithiophosphates give rise to ash, which contributes to particulate matter in automotive exhaust emissions, and regulatory agencies are seeking to reduce emissions of zinc into the environment. In addition, phosphorus, also a component of ZDDP, is suspected of limiting the service life of the catalytic converters that are used on cars to reduce pollution. It is important to limit the particulate matter and pollution formed during engine use for toxicological and environmental reasons, but it is also important to maintain undiminished the anti-wear properties of the lubricating oil.
In view of the aforementioned shortcomings of the known zinc and phosphorus-containing additives, efforts have been made to provide lubricating oil additives that contain neither zinc nor phosphorus or, at least, contain them in substantially reduced amounts.
Illustrative of non-zinc, i.e., ashless, non-phosphorus-containing lubricating oil additives are the reaction products of 2,5-dimercapto-1,3,4-thiadiazoles and unsaturated mono-, di-, and tri-glycerides disclosed in U.S. Pat. No. 5,512,190 and the dialkyl dithiocarbamate-derived organic ethers of U.S. Patent No. 5,514,189.
U.S. Pat. No. 5,512,190 discloses an additive that provides anti-wear properties to a lubricating oil. The additive is the reaction product of 2,5-dimercapto-1,3,4-thiadiazole and a mixture of unsaturated mono-, di-, and triglycerides. Also disclosed is a lubricating oil additive with anti-wear properties produced by reacting a mixture of unsaturated mono-, di-, and triglycerides with diethanolamine to provide an intermediate reaction product and reacting the intermediate reaction product with 2,5-dimercapto-1,3,4 thiadiazole.
U.S. Pat. No. 5,514,189 discloses that dialkyl dithiocarbamate-derived organic ethers have been found to be effective anti-wear/antioxidant additives for lubricants and fuels.
U.S. Pat. Nos. 5,084,195 and 5,300,243 disclose N-acyl-thiourethane thioureas as anti-wear additives specified for lubricants or hydraulic fluids.
U.S. application Ser. No. 09/872,722, filed Jun. 1, 2001, discloses a composition comprising:
(A) a lubricant, and
(B) at least one 5-alkyl-2-mercapto-1,3,4-oxadiazole compound of the formula:
wherein R
1
is a hydrocarbon or functionalized hydrocarbon of from 1 to 30 carbon atoms.
The disclosures of the foregoing references are incorporated herein by reference in their entirety.
SUMMARY OF THE INVENTION
The present invention relates to compounds of the formula
wherein R
1
is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, aryl, alkyl ether, and alkyl ester, and R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, and aryl. The alkyl moiety can also contain within it oxygen ether, ester, and amide groups.
In the above structural formulas, R
1
can be a straight or branched chain, fully saturated or partially unsaturated, hydrocarbon moiety, preferably comprising alkyl or alkenyl having from 1 to 30 carbon atoms, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, phenyl, furfuryl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, oleyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, triacontyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, oleenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, triacontenyl, and the like, and isomers and mixtures thereof. Additionally, R
1
can be a straight or branched chain, a fully saturated or partially unsaturated hydrocarbon chain, preferably having from 1 to 30 carbon atoms, within which may be ester groups or heteroatoms, such as, oxygen and nitrogen, which may take the form of ethers, polyethers, esters, and amides.
The 1,3,4-oxadiazole compounds employed in the practice of this invention are useful as ashless, non-phosphorus-containing anti-fatigue, anti-wear, extreme pressure additives for lubricating oils. They may also provide anti-corrosion and antioxidant properties. The present invention also relates to lubricating oil compositions comprising a lubricating oil and a functional property-improving amount of at least one 1,3,4-oxadiazole compound of the above formula. More particularly, the present invention is directed to a composition comprising:
(A) a lubricant, and
(B) at least one 1,3,4-oxadiazole compound of the formula:
wherein
wherein R
1
is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, aryl, alkyl ether, and alkyl ester; p
2
R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, and aryl; and
any alkyl moiety can optionally contain within it oxygen ether, ester, or amide groups.
It is preferred that the 1,3,4-oxadiazole is present in the compositions of the present invention in a concentration in the range of from about 0.01 to about 10 wt %.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The 1,3,4-oxadiazole compounds of the present invention are compounds of the formula:
wherein
wherein R
1
is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, aryl, alkyl ether, and alkyl ester;
R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, and aryl; and
any alkyl moiety can optionally contain within it oxygen ether, ester, or amide groups.
In the above structural formula, R
1
is preferably an alkyl or alkenyl moiety of 1 to 30 carbon atoms, more preferably of 1 to 22 carbon atoms, most preferably of 1 to 17 carbon atoms, and can have either a straight chain or a branched chain, which can be fully saturated or partially unsaturated, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, phenyl, furfuryl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, oleyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, triacontyl, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, oleyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl, triacontenyl, and the like, and isomers, e.g., 1-ethylpentyl, 2-ethylhexyl, and mixtures thereof Where R
1
is alkyl, it can be either a straight or a branched hydrocarbon chain, a fully saturated or partially unsaturated hydrocarbon chain, wherein said chains may contain ester groups or heteroatoms, such as oxygen and/or nitrogen, which may take the form of ethers, polyethers, esters, amides, and the like. As employed herein, the term “alkyl” is also intended to include “cycloalkyl.” Where the alkyl is cyclic, it preferably contains from 3 to 9 carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, and the like. Cycloalkyl moieties having 5 or 6 carbon atoms, i.e., cyclopentyl or cyclohexyl, are more preferred.
R
2
, R
3
, and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkaryl, and aryl; wherein any alk
Johnson Jerry D.
Reitenbach Daniel
Uniroyal Chemical Company, Inc.
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