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
2004-03-16
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...
C508S371000
Reexamination Certificate
active
06706671
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-containing anti-wear, anti-fatigue, and extreme pressure additives derived from alkyl-succinhydrazides, i.e., 4-alkyl-1,2-dihydropyridazine-3,6-diones.
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. Pat. 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. No. 3,284,234 discloses a stabilized cellulosic material which comprises a cellulosic material impregnated with at least 0.1 percent by weight of the cellulosic material of a hydrazide selected from the group consisting of the following compounds and mixtures thereof:
(a) RCONHNH
2
(II) RCONHNHCOR
(III) R′(CONHNH
2
)
2
wherein each R is independently selected from the group consisting of hydrogen and alkyl containing from 1 to 2 carbon atoms and wherein R′ is selected from the group consisting of (—CH
2
—)
n
, wherein n is an integer having a value of 0 to 5 and an alkylene of 2 to 6 carbon atoms interrupted by from 1 to 2 atoms selected from the group consisting of oxygen and sulfur.
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.
German Patent 1,260,137 discloses ethylene polymers that are said to exhibit reduced film blocking that are prepared by adding fatty acid hydrazides with more than six carbon atoms in addition to the usual internal lubricants. Lauroyl hydrazide, palmitoyl hydrazide, and stearoyl hydrazide were specifically used.
Japanese Published Application No. 03140346 discloses rigid vinyl chloride resin compositions said to have improved processability comprising 100 parts vinyl chloride resins and 3-20 parts of compounds selected from (R
1
CONH)
2
(CH
2
)
n
(wherein R
1
is an OH-substituted C
1
-C
23
alkyl and n is 1-10), (R
2
CONH)
2
(CH
2
)
n
(wherein R
2
is an OH-substituted C
4
-C
23
alkyl and n is 1-10), R
3
CONHNH
2
(wherein R
3
is an OH-substituted C
4
-C
23
alkyl), R
4
NHCONHR
5
(wherein R
4
is an OH-substituted alkyl, and R
6
NHCONH)
2
R
7
(wherein R
6
is an OH-substituted C
7
-C
23
alkyl and R
7
is a C
1
-C
10
alkylene, phenylene, or phenylene derivative). Stearic acid hydrazide and capric acid hydrazide are specifically mentioned.
U.S. application Ser. No. 09/871,120 filed May 31, 2001, discloses a composition comprising:
(A) a lubricant, and
(B) at least one alkyl hydrazide compound of the formula:
wherein R
1
is a hydrocarbon or functionalized hydrocarbon of from 1 to 30 carbon atoms, R
2
and R
3
are independently selected from the group consisting of hydrocarbon or functionalized hydrocarbons of from 1 to 30 carbon atoms and hydrogen.
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 a linear or branched alkyl, alkenyl, alkaryl, alkyl ether, or alkyl ester group, preferably of from 1 to 30 carbon atoms;
R
2
is hydrogen, a linear or branched alkyl, alkenyl, alkyl ether, or alkyl ester group, preferably of from 1 to 30 carbon atoms; and
R
3
and R
4
can be the same or different while being hydrogen or a linear or branched alkyl, aryl, alkenyl, or alkaryl group, preferably of from 1 to 30 carbon atoms.
The alkyl-succinhydrazide compounds of this invention are useful as ashless, non-phosphorus, non-sulfur-containing anti-fatigue, anti-wear, extreme pressure, anti-corrosion additives for lubricating oils.
The present invention also relates to lubricating oil compositions comprising a lubricating oil and a functional property-improving amount of at least one alkyl-succinhydrazide compound of the above formula. More particularly, the present invention is directed to a composition comprising:
(A) a lubricant, and
(B) at least one alkyl succinhydrazide compound of the formula:
wherein:
R
1
is selected from the group consisting of linear or branched alkyl, alkenyl, alkaryl, alkyl ether, alkyl ester, and alkylene ester groups;
R
2
is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkyl ether, and alkyl ester groups; and
R
3
and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl and alkenyl groups, aryl groups, and alkaryl groups.
Preferably, the alkyl-succinhydrazide 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 alkyl-succinhydrazide compounds of the present invention are compounds of the formula:
wherein:
R
1
is selected from the group consisting of linear or branched alkyl, alkenyl, alkaryl, alkyl ether, and alkyl ester groups;
R
2
is selected from the group consisting of hydrogen, linear or branched alkyl, alkenyl, alkyl ether, and alkyl ester groups; and
R
3
and R
4
are independently selected from the group consisting of hydrogen, linear or branched alkyl and alkenyl groups, aryl groups, and alkaryl groups.
In the above structural formula, where R
1
, R
2
, R
3
and/or R
4
comprise an alkyl or alkenyl moiety, such moiety can be a straight or branched hydrocarbon chain, fully saturated or partially unsaturated, preferably having from 1 to 30 carbon atoms, more preferably 1 to 22, most preferably 1 to 18 carbon atoms, e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, 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, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, tetracosenyl, pentacosenyl
Dilworth Michael P.
Johnson Jerry D.
Uniroyal Chemical Company, Inc.
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