Amine salt of N-triazolyl-hydrocarbyl succinamic acid and lubricating oil composition containing same

An amine salt of N-triazolyl-hydrocarbyl succinamic acid represented by the formula: ##STR1## in which R"" is an alkylene radical having from 2 to 24 carbon atoms and R'" is hydrogen or a hydrocarbyl radical having from 1 to 24 carbon atoms at least one R'" being a hydrocarbyl radical and a lubricating oil composition containing same is provided.

BACKGROUND OF THE INVENTION 
1. Field of Invention 
The present invention relates to amine salts of N-triazolyl-hydrocarbyl 
succinamic acids and to lubricating oil compositions containing same. 
The operational efficiency and reliability of an internal combustion engine 
is vitally dependent on the lubricating oil composition employed in the 
engine. The oil composition must provide effective lubrication over a wide 
temperature range including cold and occasionally sub-zero engine starting 
temperatures, low temperature stop-and-go driving conditions, and high 
speed, high engine operating temperatures. An effective lubricant must 
also exhibit thermal stability, anti-wear, load-carrying and 
anti-oxidation properties for extended operating periods. In the case of 
gas turbine engines, the lubricating oil composition is subjected to 
internal engine operating temperatures ranging as high as 500.degree. F. 
or higher which puts an extreme stress on the stability of the oil. 
Because of the noted requirements, lubricating oil compositions are 
constantly under investigation to improve their effectiveness for 
providing the required properties as well as to extend the length of their 
service life. Additive candidates are continuously being introduced into 
base oils to form new experimental lubricant compositions and the more 
promising new lubricants identified in screening tests are further tested 
to determine their effectiveness under representative operating 
conditions. 
2. Description of the Prior Art 
It is known in the art that the addition of an azole compound to a 
synthetic lubricating oil composition will improve the copper corrosion 
properties of the lubricating composition. The azole type additives, 
including such compounds as 3-amino-triazole and 4-amino-triazole, are 
known as copper passivators. It has been theorized that these compounds 
attach themselves to the surface of the copper substrate to deactivate or 
reduce the corrosiveness of the copper metal that is in contact with the 
hot lubricating oil composition. Examples of this are U.S. Pat. No. 
4,064,059, U.S. Pat. No. 3,756,952, U.S. Pat. No. 3,247,111 and British 
Pat. No. 1,180,387 which are incorporated herein by reference. 
Despite the extensive art relating to lubricating oil compositions, there 
still remain problems which are not solved by the compositions known in 
the art. There is still a need for additives which lead to the production 
of lubricating oil compositions with improved oxidation resistance, rust 
inhibiting and metal deactivating properties. None of the prior art 
lubricating oil compositions which employ azole type additives are 
completely satisfactory for these purposes. 
Accordingly, it is an object of this invention to provide an amine salt of 
an N-triazolyl hydrocarbyl-substituted succinamic acid which can be 
incorporated into a lubricating oil composition. 
It is also an object of this invention to provide a lubricating oil 
composition containing the amine salt of an N-triazolyl 
hydrocarbyl-substituted succinamic acid which exhibits outstanding rust 
inhibiting properties in addition to thermal and oxidation stability and 
copper metal passivity. 
The advantages and objects of this invention will become apparent to those 
skilled in the art from the following discussion and accompanying 
examples. 
SUMMARY OF THE INVENTION 
It has been found that novel amine salts of N-triazolyl 
hydrocarbyl-substituted succinamic acids can be prepared by reacting a 
hydrocarbyl-substituted succinic anhydride with 3-amino-1,2,4-triazole to 
form an intermediate hydrocarbyl-succinamic acid followed by a reaction of 
this hydrocarbyl-succinamic acid with a hydrocarbyl amine to form the 
noted compound. These compounds have excellent stability and are 
particularly useful as additives in lubricating oil compositions. 
Novel lubricating oil compositions which exhibit outstanding rust 
inhibiting properties together with oxidation stability and corrosion 
inhibition containing the noted amine salt of an N-triazolyl 
hydrocarbyl-substituted-succinamic acid are also contemplated. 
DESCRIPTION OF THE PREFERRED EMBODIMENTS 
In accordance with this invention, an amine salt of an N-triazolyl 
hydrocarbyl-substituted succinamic acid is prepared in a two-step process. 
In the first step of the reaction, 3-amino-1,2,4-triazole is reacted with 
a hydrocarbyl-substituted succinic anhydride to produce as an intermediate 
reaction product a hydrocarbyl-substituted-N-(3-[1,2,4-triazolyl]) 
succinamic acid. 
The hydrocarbyl-substituted succinic anhydride reactant is represented by 
the following formula: 
##STR2## 
in which R'''' represents a hydrocarbyl radical having from 2 to 24 carbon 
atoms. The hydrocarbyl radical in the succinic anhydride can be saturated 
or unsaturated. A preferred hydrocarbyl-substituted succinic anhydride is 
one in which the hydrocarbyl radical represented by R'''' has from 2 to 18 
carbon atoms. 
A more preferred hydrocarbyl-substituted succinic anhydride is represented 
by the formula: 
##STR3## 
in which R.sub.x and R.sub.y alternately represent hydrogen and a 
monovalent unsaturated hydrocarbon radical having from 6 to 16 carbon 
atoms. 
Examples of suitable hydrocarbyl-substituted succinic anhydride reactants 
include dipropenyl succinic anhydride, tripropenyl succinic anhydride, 
tetrapropenyl succinic anhydride, pentapropenyl succinic anhydride, 
hexapropenyl succinic anhydride, decenyl succinic anhydride, t-octyl 
succinic anhydride, dodecenyl succinic anhydride, tetradecyl succinic 
anhydride, tetradecenyl succinic anhydride, hexadecenyl succinic anhydride 
and octadecenyl succinic anhydride. 
The reaction between 3-amino-1,2,4-triazole and the prescribed hydrocarbon 
substituted succinic anhydride to produce an 
N-triazolyl-hydrocarbyl-substituted succinamic acid is depicted in the 
following formulas: 
##STR4## 
in which R.sub.x and R.sub.y have the values noted above. 
The above reaction is preferably conducted using approximately equimolar 
amounts of the 3-amino-1,2,4-triazole optionally written as 
3-amino-1H,-1,2,4-triazole and the hydrocarbyl- or alkenyl-substituted 
succinic anhydride reactants. The molar ratio may be varied by employing 
from about 0.7 to 1.3 moles of the 3-amino-1,2,4-triazole per mole of the 
hydrocarbyl-substituted succinic anhydride. 
This reaction is preferably conducted in the presence of an inert solvent. 
Any inert hydrocarbon solvent that is liquid under the reaction conditions 
is generally satisfactory. Examples of solvents which can be used to 
conduct this reaction include benzene, toluene, n-heptane, xylene and 
similar aliphatic and aromatic solvents. 
This reaction can be conducted at a temperature ranging from room 
temperature up to the decomposition temperature of the reactants. It is 
preferred, however, to conduct this reaction at the reflux temperature of 
the solvent being employed for a sufficient length of time to complete the 
reaction.

The following examples illustrate the preparation of the intermediate or 
precursor N-(3-[1,2,4-triazole]) hydrocarbyl-substituted succinamic acid. 
EXAMPLE 1 
Mixture of 2-and 3-Dodecyl-N-(3-[1,2,4-Triazolyl]) Succinamic Acid 
26.8 g. (0.1 mole) dodecyl succinic anhydride, 8.4 g. (0.1 mole) 
3-amino-1H-1,2,4-triazole and 150 ml. of benzene were heated at reflux for 
four hours with stirring. Concentration under reduced pressure afforded 
the product. Yield: 35 g. % N Calc. 15.9 Found: 16.6. 
EXAMPLE 2 
Mixture of 2-and 3-Tetrapropenyl-N-(3-[1,2,4-Triazolyl]) Succinamic Acid 
8.4 g. (0.1 mole) of 3-amino-1H-1,2,4-triazole, 26.6 g. (0.1 mole) 
tetrapropenyl succinic anhydride and 100 ml. of benzene were heated at 
reflux for four hours with stirring. Concentration under reduced pressure 
afforded the product. Yield=34 g. % N Calc. 15.9 Found 16.0. 
EXAMPLE 3 
Mixture of 2-and 3-Tetradecenyl-N-(3-[1,2,4-Triazolyl]) Succinamic Acid 
14.5 g. of tetradecenyl succinic anhydride, 4.2 g. of 
3-amino-1H-1,2,4-triazole and 75 ml. of benzene were heated at reflux for 
two hours. Filter off small amount of benzene insolubles. Concentrate 
filtrate to afford the product as a waxy solid. %N Calc.--14.8 
Found--14.1. 
Other typical intermediate or precursor N-(3-[1,2,4-triazolyl]) 
hydrocarbyl-substituted succinamic acids include 
2-decenyl-N-(3-[1,2,4-triazolyl]) succinamic acid, 2- and 
3-octenyl-N-(3-[1,2,4-triazolyl]) succinamic acid, 2- and 
3-hexadecenyl-N-(3-[1,2,4-triazolyl]) succinamic acid, 
3-octadecenyl-N-(3-[1,2,4-triazolyl]) succinamic acid, 2-and 
3-eicosenyl-N-(3-[1,2,4-triazolyl]) succinamic acid and 2- and 
3-dodecenyl-N-(3-[1,2,4-triazolyl]) succinamic acid. 
The intermediate N-triazolyl hydrocarbyl-substituted succinamic acid does 
not possess the required properties for the contemplated lubricating oil 
composition of this invention and must be reacted with a hydrocarbyl amine 
defined below to produce the prescribed amine salt of N-triazolyl 
hydrocarbyl succinamic acid. 
The amine salts of N-triazolyl-hydrocarbyl succinamic acids impart valuable 
rust inhibiting properties to lubricating oil compositions while the 
N-triazolyl hydrocarbyl succinamic acids do not. This difference in 
performance is not fully understood but may be accounted for by the 
different chemical and structural features of the amine salts. 
The hydrocarbyl amine reactant which can be employed in the second step of 
the process for the preparation of the prescribed novel amine salt 
compound of the invention is a primary or secondary aliphatic or aromatic 
amine represented by the formula: 
EQU R.sub.2 '"--NH 
in which R"' is a hydrogen or a hydrocarbyl radical having from 1 to 24 
carbon atoms, at least one R"' being a hydrocarbyl radical. 
The preferred amine is a saturated aliphatic hydrocarbon primary amine 
represented by the formula R"'NH.sub.2 in which R"' represents a 
monovalent saturated aliphatic hydrocarbon radical having from 1 to 22 
carbon atoms. The most preferred amines are those in which R"' is a 
monovalent aliphatic hydrocarbon radical having from 8 to 18 carbon atoms. 
Examples of suitable amines for preparing the amine salt of N-triazolyl 
hydrocarbyl succinamic acid include methylamine, ethylamine, propylamine, 
n-butylamine, n-hexylamine, n-octylamine, t-octylamine, decylamine, 
dodecylamine, tetradecylamine, C.sub.11 -C.sub.14 -tertiary alkyl primary 
amine, C.sub.18 -C.sub.22 -tertiary alkyl primary amine, stearylamine, 
oleylamine, laurylamine, dicyclohexylamine, dioctylamine and 
didodecylamine. 
The prescribed hydrocarbyl amine and N-triazolyl hydrocarbyl succinamic 
acid are mixed neat or in an inert hydrocarbon solvent for sufficient time 
to complete the formation of the prescribed amine salt of N-triazolyl 
hydrocarbyl succinamic acid. Equimolar amounts of the hydrocarbyl amine 
and of the N-triazolyl hydrocarbyl succinamic acid are preferably employed 
in this reaction. It is possible, however, to employ from about 0.75 to 
1.25 moles of hydrocarbylamine with a mole of N-triazolyl hydrocarbyl 
succinamic acid to produce a product containing a major amount of the 
prescribed amine salt of N-triazolyl hydrocarbyl succinamic acid. This 
reaction is facilitated by using one of the inert solvents employed in the 
first step of the reaction using an elevated temperature ranging from room 
temperature to the reflux temperature of the solvent. 
The following examples illustrate amine salts of N-triazolyl hydrocarbyl 
succinamic acids which can be prepared by reacting an intermediate 
hydrocarbyl-N-(3-[1,2,4-triazolyl]) succinamic acid with a hydrocarbyl 
amine by refluxing approximately equimolar amounts of said amine and said 
intermediate in benzene for a reaction period of 11/2 to 21/2 hours. A 
quantitative yield of the product is obtained on removal of the solvent 
under reduced pressure. 
EXAMPLE 4 
Approximately equimolar amounts of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl 
succinamic acid and tertiary octyl amine were reacted as described above 
to form the tert-octylamine salt of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl 
succinamic acid represented by the formula: 
##STR5## 
This compound was amber colored when molten and white in powder form. It 
had a melting point of 77.degree.-82.degree. C. 
______________________________________ 
Elemental Analysis: 
Found Theory 
______________________________________ 
% N 14.4 14.6 
% C 65.1 65.1 
% H 10.2 10.2 
______________________________________ 
The infrared spectrum was consistent with the compound structure and gave 
the following band values: 
______________________________________ 
IR band, cm.sup.-1 Assignment 
______________________________________ 
1540 Amide II 
1580 --CO.sub.2.sup..crclbar. 
1630 --N.dbd.N-- 
1680 Amide I 
2720 NH.sub.2.sup.+ 
______________________________________ 
EXAMPLE 5 
Tertiary Octyl Amine Salt of 2-Dodecyl-N-(3-[1,2,4-Triazolyl])-Succinamic 
Acid and the corresponding 3-Dodecyl derivative. 
EXAMPLE 6 
Tertiary Octyl Amine Salt of 
2-Tetrapropenyl-N-(3-[1,2,4-Triazolyl])-Succinamic Acid and the 
corresponding 3-Tetrapropenyl derivative. 
EXAMPLE 7 
Tertiary C.sub.18-22 Alkyl Amine Salt of 
2-Dodecyl-N-(3-[1,2,4-Triazolyl])-Succinamic Acid and the corresponding 
3-Dodecyl derivative. 
EXAMPLE 8 
Tertiary C.sub.11-14 Alkyl Amine Salt of 
2-Dodecyl-N-(3-[1,2,4-Triazolyl])-Succinamic Acid and the corresponding 
3-Dodecyl derivative. 
EXAMPLE 9 
Dicyclohexyl Amine Salt of 2-Dodecyl-N-(3-[1,2,4-Triazolyl])-Succinamic 
Acid and the corresponding 3-Dodecyl derivative. 
EXAMPLE 10 
Secondary C.sub.15 alkyl amine salt of 2-dodecyl-N-(3-[1,2,4-triazolyl]) 
succinamic acid. 
EXAMPLE 11 
n-Butyl amine salt of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl succinamic 
acid. 
EXAMPLE 12 
n-Hexylamine salt of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl succinamic 
acid. 
EXAMPLE 13 
n-Octylamine salt of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl succinamic 
acid. 
EXAMPLE 14 
n-Decylamine salt of N-(3-[1,2,4-triazolyl])-2-dodecen-1-yl succinamic 
acid. 
The novel amine salt of N-triazolyl-hydrocarbyl succinamic acid of the 
invention is highly effective as an anti-rust additive as well as 
providing other valuable properties in a lubricating oil composition. The 
oil substrate may be a mineral, a synthetic or mixed mineral-synthetic 
lubricating oil. The synthetic oil substrates include ester base oils, 
alkylene polymers, alkylene epoxide type polymers, alkylbenzenes, 
polyphenyls and the like. 
The hydrocarbon mineral oil base can be a paraffin base, a naphthene base 
or a mixed paraffin-naphthene base oil. The mineral lubricating oil base 
will generally have been subjected to solvent refining to improve its 
lubricity and viscosity temperature relationship as well as solvent 
dewaxing to remove waxy components and improve the pour of the oil. 
Generally, mineral lubricating oils having an SUS viscosity at 100.degree. 
F. between 50 and 500 may be used in the formulation of the improved 
lubricants of this invention, although the preferred viscosity range will 
be from about 70 and 300 SUS at 100.degree. F. A blend of mineral base 
oils can be employed to provide a suitable base oil for either a single or 
multigrade motor oil. The base oil will constitute from about 85 to 99% or 
more of the lubricant composition. 
The lubricating composition of the invention can contain from about 0.01 to 
5 percent by weight of the prescribed amine salt additive. It is 
preferred, however, to employ from about 0.05 to 0.5 weight percent. This 
lubricant composition may also contain anti-wear, load carrying, 
anti-oxidation, viscosity index improving and detergentdispersant 
additives each in the amounts within the range from about 0.1 to 10% by 
weight. 
The following examples are illustrative of the lubricating compositions of 
the invention, all percentages being by weight. 
EXAMPLE 15 
A mineral lubricating oil having an SUS of 100 at 100.degree. F. containing 
0.05% of the product of Example 4. 
EXAMPLE 16 
A paraffin base mineral lubricating oil having an SUS of 125 at 100.degree. 
F. containing 0.1 weight percent of the tertiary octylamine salt of 
2-dodecyl-N-(3-[1,2,4-triazolyl]) succinamic acid. 
EXAMPLE 17 
A mixed paraffinic-naphthenic mineral lubricating oil having an SUS 
viscosity of 100 at 100.degree. F. containing 0.2% of the tertiary 
octylamine salt of 2-tetrapropenyl-N-(3-[1,2,4-triazolyl]) succinamic 
acid. 
EXAMPLE 18 
A synthetic lubricating oil consisting of an ester base formed from 
pentaerythritol and a mixture of C5 to C9 monocarboxylic acids having a 
viscosity of 25.6 cs at 100.degree. F. containing 0.05 weight percent of 
the product of Example 4. 
EXAMPLE 19 
A mixed paraffinic mineral oil and synthetic pentaerythritol ester base 
lubricating oil having a viscosity of 100 at 100.degree. F. containing 0.5 
weight percent of the tertiary octylamine salt of 
2-dodecenyl-N-(3-[1,2,4-triazolyl]) succinamic acid. 
The particularly preferred lubricating oil composition of the invention is 
a synthetic aliphatic ester base lubricating oil composition. In general, 
the base oil employed in this type of lubricant comprises an ester base 
fluid prepared from pentaerythritol or trimethylolpropane and a mixture of 
aliphatic hydrocarbon monocarboxylic acids. The preferred hydrocarbon 
monocarboxylic acids for forming the base oil or ester base fluid are the 
straight-chain or branched-chain aliphatic monocarboxylic acids having 
from about 2 to 18 carbon atoms and preferably having from about 5 to 10 
carbon atoms. Examples of suitable specific aliphatic acids include acetic 
acid, propionic acid, butyric acid, valeric acid, isovaleric acid, caproic 
acid, decanoic acid and the like. Generally, an ester based lubricating 
oil composition will contain a base oil or ester base fluid formed from a 
mixture of esters such as the esters formed from pentaerythritol and a 
mixture of C5 to C10 aliphatic monocarboxylic acids selected to provide 
desired viscosity properties. An example of a specific ester base fluid is 
a tetraester formed from pentaerythritol and a mixture of aliphatic 
monocarboxylic acids comprising 38% valeric acid, 13% 2-methylpentanoic 
acid, 32% octanoic acid and 17% pelagonic acid. Another effective ester 
base fluid is the triester formed from trimethylolpropane and a mixture of 
aliphatic monocarboxylic acids consisting of 2% valeric, 9% caproic, 13% 
heptanoic, 7% octanoic acid, 3% caprylic acid, 65% pelagonic acid and 1% 
capric acid. 
An ester base blend is employed for preparing synthetic aircraft turbine 
lubricating oil compositions. A conventional ester base blend comprises 
the base oil or ester base fluid and from about 0.3 to 5% by weight of a 
naphthylamine derivative, such as phenyl alpha naphthylamine or an alkyl 
or alkaryl-substituted phenyl naphthylamine in which the alkyl and alkaryl 
radicals have from 1 to 12 carbon atoms, from about 0.3 to 5% of a 
dialkyldiphenylamine in which the alkyl radicals have from 1 to 12 carbon 
atoms and particularly from 4 to 12 carbon atoms, from about 0.25 to 10 
weight percent of a trihydrocarbyl phosphate in which the hydrocarbyl 
radical contains a aryl ring and contains from about 6 to 18 carbon atoms, 
and, optionally, from about 0.04 to 2 weight percent of a 
polyhydroxy-substituted anthraquinone, such as quinizarin. A very small 
proportion, e.g., from about 1 to 50 ppm (parts per million) of a silicone 
anti-foam agent, such as dimethyl silicone and diethyl silicone can also 
optionally be employed. 
Concentrates of the novel additive of the invention can be prepared using a 
mineral oil, synthetic oil, or mixed oil base containing from 5 to 50 
weight percent of the additive. 
The following examples illustrate specific ester base blends which are 
useful for preparing synthetic lubricating oil compositions of the 
invention. 
EXAMPLE 20 
Ester Base Blend A 
An ester base blend was prepared consisting of 1.0% 
p,p'-di-tert.-octyldiphenylamine, 1.5 weight percent of 
N-(p-t-octylphenyl)-1-naphthylamine, 2.0 weight percent of 
tricresylphosphate and the balance a pentaerythritol ester base oil made 
from pentaerythritol and a mixture of aliphatic monocarboxylic acids 
having from 5 to 9 carbon atoms which ester base oil had viscosities in 
centistokes of 5.01 at 210.degree. F., 25.6 at 100.degree. F. (ASTM Method 
D 445) and 7005 at -40.degree. F. and a viscosity index of 140. 
EXAMPLE 21 
Ester Base Blend B 
Ester base blend B consisted of 1.0 weight percent of phenyl alpha 
naphthylamine, 1.0 weight percent of p,p'-di-tert.-octyldiphenylamine, 2.0 
weight percent tricresyl phosphate, 0.1 weight percent quinizarin and the 
balance about 95.8 weight percent of an ester base oil formed from 
pentaerythritol and a mixture of aliphatic monocarboxylic acid having from 
5 to 10 carbon atoms, said ester base oil having kinematic viscosities in 
centistokes of about 5.10 at 210.degree. F. and about 24.5 at 100.degree. 
F. 
The rust-inhibiting properties of a lubricating oil composition of the 
invention was determined by preparing a synthetic lubricating oil 
composition and submitting it for testing against Military Specifications 
MIL-L-2369. 
EXAMPLE 22 
A pentaerythritol-aliphatic ester base lubricating oil composition was 
prepared by blending 0.1 weight percent of the additive of Example 4 into 
Ester Base Blend B to form a synthetic lubricating oil composition, 
designated Synthetic Lubricant B. This lubricant was then tested for 
rustinhibiting properties. 
Synthetic Lubricant B passed both the Navy Laboratory Rust Test and 
MIL-L-23699 Bench Tests. The same lubricant was further tested by an 
independent Research Institute in the J-57 Turbine Engine Simulator Test 
which it passed with a cleaner performance than a qualified MIL-L-23699 
oil. 
Used oil samples of Lubricant B from both the Erdco Bearing Test and from 
the Navy's T63 Engine Test were further tested in the Navy Laboratory Rust 
Test and found to have no apparent loss in rust protective properties. 
Ester base oil compositions of the invention based on Ester Base Blend A 
were tested in the 400.degree. F./72 hour and 425.degree. F./48 hour 
Oxidation-Corrosion Tests in accordance with Method 5308.4 a Federal Test 
Method and Standard No. 791a (issued December 31, 1961) except for 
modifications to conform to MIL-L-23699B specifications. 
EXAMPLE 23 
Lubricating oil compositions were prepared by blending 0.1 weight percent 
each of tertiary octyl amine salts of 
2-dodecyl-N-(3-[1,2,4-triazolyl])-succinamic acid, tertiary octyl amine 
salt of 2-tetrapropenyl-N(3-[1,2,4-triazolyl])-succinamic acid, tertiary 
C.sub.18-22 alkyl amine salt of 
2-dodecyl-N-(3-[1,2,4-triazolyl])-succinamic acid, and dicyclohexyl amine 
salt of 2-dodecyl-N-(3-[1,2,4-triazolyl])-succinamic acid into Ester Base 
Blend A to form synthetic lubricant compositions. These lubricant 
compositions were then tested in the 400.degree. F./72 hour and 
425.degree. F./48 hour Oxidation-Corrosion Tests. All of these lubricant 
compositions were found to possess outstanding oxidation and 
corrosion-inhibiting properties in these industry adopted tests. 
The novel amine salts of N-triazolyl-hydrocarbyl succinamic acid of the 
invention are surprisingly effective as additives for lubricating oil 
compositions. A particularly unexpected result was the discovery of their 
rustinhibiting properties which promises to provide new classes of 
lubricating oil compositions needed to satisfy military aircraft 
requirements.