U.S. patent application number 12/337813 was filed with the patent office on 2010-06-24 for friction modifiers and/or wear inhibitors derived from hydrocarbyl amines and cyclic carbonates.
This patent application is currently assigned to Chevron Oronite Company LLC. Invention is credited to William R. Ruhe, JR..
Application Number | 20100160198 12/337813 |
Document ID | / |
Family ID | 42266998 |
Filed Date | 2010-06-24 |
United States Patent
Application |
20100160198 |
Kind Code |
A1 |
Ruhe, JR.; William R. |
June 24, 2010 |
FRICTION MODIFIERS AND/OR WEAR INHIBITORS DERIVED FROM HYDROCARBYL
AMINES AND CYCLIC CARBONATES
Abstract
A lubricating oil composition comprising a major amount of base
oil of lubricating viscosity and a minor amount of an additive
comprising the reaction product obtained by reacting a cyclic
carbonate and a hydrocarbyl amine having the formula:
R.sup.1R.sup.2NH in which R.sup.1 is hydrogen, or a hydrocarbyl
group containing 1 to 40 carbon atoms, and R.sup.2 is a hydrocarbyl
group containing 1 to 40 carbon atoms.
Inventors: |
Ruhe, JR.; William R.;
(Benicia, CA) |
Correspondence
Address: |
CHEVRON CORPORATION
P.O. BOX 6006
SAN RAMON
CA
94583-0806
US
|
Assignee: |
Chevron Oronite Company LLC
|
Family ID: |
42266998 |
Appl. No.: |
12/337813 |
Filed: |
December 18, 2008 |
Current U.S.
Class: |
508/464 |
Current CPC
Class: |
C10N 2040/25 20130101;
C10N 2070/00 20130101; C10M 2215/10 20130101; C10N 2040/04
20130101; C10N 2020/069 20200501; C10M 2227/09 20130101; C10M
2215/28 20130101; C10M 2207/289 20130101; C10N 2030/06 20130101;
C10N 2040/08 20130101; C10N 2020/071 20200501; C10N 2010/04
20130101; C10M 133/18 20130101; C10M 2223/045 20130101; C10M
2207/289 20130101; C10N 2060/14 20130101; C10M 2223/045 20130101;
C10N 2010/04 20130101; C10M 2215/28 20130101; C10N 2060/10
20130101; C10M 2215/28 20130101; C10N 2010/12 20130101; C10M
2215/28 20130101; C10N 2010/12 20130101; C10M 2223/045 20130101;
C10N 2010/04 20130101; C10M 2215/28 20130101; C10N 2060/10
20130101; C10M 2207/289 20130101; C10N 2060/14 20130101 |
Class at
Publication: |
508/464 |
International
Class: |
C10M 129/84 20060101
C10M129/84 |
Claims
1. A lubricating oil composition comprising a major amount of base
oil of lubricating viscosity and a minor amount of an additive
comprising the reaction product obtained by reacting a cyclic
carbonate and a hydrocarbyl amine having the formula (I):
R.sup.1R.sup.2NH (I) in which R.sup.1 is hydrogen, or a hydrocarbyl
group containing 1 to 40 carbon atoms, and R.sup.2 is a hydrocarbyl
group containing 1 to 40 carbon atoms.
2. The lubricating oil composition of claim 1 wherein R.sup.1 is
hydrogen, or a hydrocarbyl group containing 8 to 28 carbon
atoms.
3. The lubricating oil composition of claim 2, wherein said
hydrocarbyl comprises a linear and/or branched, alkyl and/or
alkenyl group.
4. The lubricating oil composition of claim 1 wherein R.sup.2 is a
hydrocarbyl group containing 8 to 28 carbon atoms.
5. The lubricating oil composition of claim 4, wherein said
hydrocarbyl comprises a linear and/or branched, alkyl and/or
alkenyl group.
6. The lubricating oil composition of claim 1 wherein said
hydrocarbyl amine is a primary amine.
7. The lubricating oil composition of claim 1 wherein said cyclic
carbonate is selected from the group consisting of ethylene
carbonate, propylene carbonate, and glycerol carbonate.
8. The lubricating oil composition of claim 1 further comprising at
least one co-additive selected from: (a) an ashless dispersant; (b)
an oxidation inhibitor; (d) a demulsifier; (e) an extreme pressure
agent; (f) a multifunctional additive; (g) a viscosity index
improver; (h) a pour point depressant; (i) a foam inhibitor; and
(j) an emulsifier.
9. The lubricating oil composition of claim 1 wherein said reaction
of said cyclic carbonate and said hydrocarbyl amine occurs at a
molar ratio of hydrocarbyl amine to cyclic carbonate of 0.5:1 to
2:1 and at a temperature range of between 60.degree. C. and
180.degree. C.
10. The lubricating oil composition of claim 9 wherein said
hydrocarbyl amine comprises oleylamine, and wherein said cyclic
carbonate comprises glycerol carbonate.
11. The lubricating oil composition of claim 1 wherein said
hydrocarbyl amine comprises 2-ethylhexylamine, and wherein said
cyclic carbonate comprises ethylene carbonate.
12. The lubricating oil composition of claim 1 wherein said
hydrocarbyl amine comprises oleylamine, and wherein said cyclic
carbonate comprises glycerol carbonate.
13. The lubricating oil composition of claim 1 wherein said
reaction product is formed prior to addition to said base oil of
lubricating viscosity.
14. The process of claim 1 wherein said additive is a wear
inhibitor or a friction modifier.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to carbamates having improved
wear inhibition and friction modifier properties as part of a
lubricating oil composition.
BACKGROUND OF THE INVENTION
[0002] Antiwear additives and friction modifying additives are
frequently blended with lubricants in order to prevent wear, reduce
fuel consumption, and increase the operating life of machinery.
Glycerol esters, such as glycerol monooleate, are well known in the
art as friction modifiers and as wear inhibitors. The problem
associated with these compounds is that the ester functionality is
easily hydrolyzed which results in the production of free oleic
acid, a corrosive agent.
[0003] In this invention, more stable carbamates have been prepared
by reacting oleylamine with glycerol carbonate or ethylene
carbonate. Surprisingly, we have found that the reaction product of
oleylamine and glycerol carbonate has exhibited good anti-wear
performance and good friction performance. Previously, only
glycerol monooleate had shown acceptable anti-wear performance. We
have also found that the reaction product of 2-ethylhexylamine and
ethylene carbonate, or the reaction product of oleylamine and
ethylene carbonate, has also exhibited good friction
performance.
SUMMARY OF THE INVENTION
[0004] This invention is directed to a lubricating oil composition
comprising a major amount of base oil of lubricating viscosity and
a minor amount of an additive comprising the reaction product
obtained by reacting a cyclic carbonate and a hydrocarbyl amine
having the formula:
R.sup.1R.sup.2NH
in which R.sup.1 is hydrogen, or a hydrocarbyl group containing 1
to 40 carbon atoms, and R.sup.2 is a hydrocarbyl group containing 1
to 40 carbon atoms. In a preferred embodiment, the cyclic carbonate
is glycerol carbonate, the hydrocarbyl amine is oleylamine, and the
reaction product is glycerol carbamate. Glycerol carbmates have
improved wear inhibition and friction modifier properties as part
of the lubricating oil composition. In other embodiments, the
carbamate is a reaction product of a cyclic carbonate, such as
ethylene carbonate, and a hydrocarbyl amine such as 2-ethylhexamine
or oleylamine.
DETAILED DESCRIPTION OF THE INVENTION
[0005] This invention relates to a carbamate additive, comprising
the reaction product of a cyclic carbonate and a hydrocarbyl amine,
which may be incorporated into a lubricating oil composition. Such
lubricating oil compositions having this additive are particularly
beneficial for reducing wear in tractor hydraulic fluids, and may
be useful in other lubricating oil applications such as engine oils
and gear oils. Such lubricating oil compositions having this
additive may also provide for excellent friction reduction
properties in the aforesaid applications.
Definitions
[0006] The term "hydrocarbyl" denotes a group having a carbon atom
directly attached to the remainder of the molecule and having
predominantly hydrocarbon character. Such groups may include the
following: (1) Hydrocarbon groups; that is, aliphatic, (e.g., alkyl
or alkenyl), alicyclic (e.g., cycloalkyl or cycloalkenyl),
aromatic, aliphatic- and alicyclic-substituted aromatic,
aromatic-substituted aliphatic and alicyclic groups, and the like.
Such groups are known to those skilled in the art, and non-limiting
examples include methyl, ethyl, octyl, decyl, octadecyl,
cyclohexyl, phenyl, individually or in combinations thereof, etc.;
(2) Substituted hydrocarbon groups; that is, groups containing
non-hydrocarbon substituents which do not alter the predominantly
hydrocarbon character of the group. Those skilled in the art will
be aware of suitable substituents, and non-limiting examples
include halo, hydroxyl, nitro, cyano, alkoxy, acyl, etc., and
optionally, (3) Hetero groups; that is, groups which, while
predominantly hydrocarbon in character within the context of this
invention, contain atoms other than carbon in a chain or ring
otherwise composed of carbon atoms. Suitable hetero atoms will be
apparent to those skilled in the art and non-limiting examples
include nitrogen, oxygen and sulfur.
[0007] "Cyclic carbonates" include those having the formula (I)
below. An example of a cyclic carbonate wherein R.sub.3 and R.sub.4
are hydrogen is ethylene carbonate. Propylene carbonate is an
example of a cyclic carbonate wherein R.sub.3 is hydrogen and
R.sub.4 is a methyl group. Glycerol carbonate is an example of a
cyclic carbonate wherein R.sub.3 is hydrogen and R.sub.4 is a
CH.sub.2--OH group.
##STR00001##
[0008] Carbamates are prepared by reaction of a hydrocarbyl amine
and a cyclic carbonate. The hydrocarbyl amine is shown by the
following formula (II):
R.sup.1R.sup.2NH Formula (II)
in which R.sup.1 is hydrogen, or a hydrocarbyl group containing 1
to 40 carbon atoms, and more preferably, 8 to 28 carbon atoms and
R.sup.2 is a hydrocarbyl group containing 1 to 40 carbon atoms, and
more preferably 8 to 28 carbon atoms. The hydrocarbyl group in
R.sup.1 and R.sup.2 may be a linear and/or branched, alkyl and/or
alkenyl group. In a preferred embodiment, the cyclic carbonate is
glycerol carbonate, the hydrocarbyl amine is oleylamine, and the
carbamate is glycerol carbamate.
[0009] Glycerol carbamates which are obtained by reaction of
glycerol carbonate with a primary, and optionally a secondary,
hydrocarbyl amine, such as saturated or unsaturated mono-amines, or
mixtures of hydrocarbyl amines derived from fatty acids, such as
coco, oleyl, or tallow, preferably, oleylamine. Non limiting
examples of primary and secondary hydrocarbyl amines include
octylamine, decylamine, dodecyl-amine, tetradecylamine,
hexadecylamine, octadecylamine, benzylamine, phenylamine,
oleylamine (for example Armeen.RTM. OLD from Akzo Nobel),
stearylamine (for example Armeen 18 D from Akzo Nobel), cocoamine,
2-ethylhexylamine, isotridecylamine, 2-butyloctylamine,
2-hexyldecylamine, 2-octyldodeylamine, cyclohexylamine,
dibenzylamine, diphenylamine, dicocoamine (for example Armeen 2C
from Akzo Nobel), di-2-ethylhexylamine, and
N-methylcyclohexylamine.
[0010] In another embodiment, carbamates are obtained by reaction
of ethylene carbonate with a primary hydrocarbyl amine, preferably
2-ethylhexylamine. In another embodiment, carbamates are obtained
by reaction of ethylene carbonate with a primary hydrocarbyl amine,
preferably oleylamine.
[0011] Glycerol carbonate can be produced by methods known from the
prior art as described, for example, in U.S. Pat. No. 6,025,504,
incorporated herein by reference in its entirety. Ethylene
carbonate can be produced by methods known from the prior art as
described, for example, in U.S. Pat. No. 4,314,945 and U.S. Pat.
No. 4,233,221, incorporated herein by reference in its
entirety.
[0012] In a preferred embodiment, glycerol carbamates are prepared
by reaction of oleylamine 1 and glycerol carbonate 2, in reaction
scheme (I) below. The reaction occurs at a molar ratio of
oleylamine to glycerol carbonate of 0.5:1 to 2:1, preferably 0.75:1
to 1.5:1 and more particularly 1:1, and at a temperature range of
between 60.degree. C. and 180.degree. C., and more preferably
between 80.degree. C. and 120.degree. C. A mixture of products is
obtained. The major products are glycerol carbamates, some general
structures of which are shown as 3 and 4. Minor products may
include glycerol, hydroxyethylamines, and dioleyl urea. Hydrocarbon
solvents or other inert solvents may be used in the reaction, such
as benzene, toluene, and xylenes.
##STR00002##
[0013] After the carbamate compounds of this invention are formed,
they may be incorporated into a lubricating oil composition
comprising a base oil of lubricating viscosity and other additive
components, by the direct blending of the carbamate compounds with
the lubricating oil composition. The amount of carbamate additive
compounds in the lubricating oil composition is present in a "minor
amount," which refers to a concentration of the additive within the
lubricating oil composition of less than about 40 wt %. In some
embodiments, a "minor amount" of additive refers to a concentration
of the additive within the lubricating oil composition of less than
about 30 wt %, of less than about 20 wt %, of less than about 10 wt
%, of less than about 1 wt %, or of less than about 0.5 wt %.
Base Oil of Lubricating Viscosity
[0014] The base oil of lubricating viscosity employed in the
present invention may be mineral oils or synthetic oils. A base oil
having a viscosity of at least 10 cSt (mm.sup.2/s) at 40.degree. C.
and a pour point below 20.degree. C., preferably at or below
0.degree. C. is desirable. The base oils may be derived from
synthetic or natural sources. Mineral oils for use as the base oil
in this invention include, for example, paraffinic, naphthenic and
other oils that are ordinarily used in lubricating oil
compositions. Synthetic oils include, for example, both hydrocarbon
synthetic oils and synthetic esters and mixtures thereof having the
desired viscosity. Hydrocarbon synthetic oils may include, for
example, oils prepared from the polymerization of ethylene or
higher alpha olefins (polyalphaolefin or PAO), or from hydrocarbon
synthesis procedures using carbon monoxide and hydrogen gases such
as in a Fisher-Tropsch process. Useful synthetic hydrocarbon oils
include liquid polymers of alpha olefins having the proper
viscosity. Especially useful are the hydrogenated liquid oligomers
of C.sub.6 to C.sub.12 alpha olefins such as 1-decene trimer.
Likewise, alkyl benzenes of proper viscosity, such as didodecyl
benzene, can be used. Useful synthetic esters include the esters of
monocarboxylic acids and polycarboxylic acids, as well as
mono-hydroxy alkanols and polyols. Typical examples are didodecyl
adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate,
dilaurylsebacate, and the like. Complex esters prepared from
mixtures of mono and dicarboxylic acids and mono and dihydroxy
alkanols can also be used. Blends of mineral oils with synthetic
oils are also useful. For example, blends of 10 wt % to 25 wt %
hydrogenated 1-decene trimer with 75 wt % to 90 wt % 150 SUS
(100F.) mineral oil make excellent lubricating oil bases.
Other Additive Components
[0015] The following additive components are examples of some other
additive components that can be favorably employed in the present
invention. These examples of additives are provided to illustrate
the present invention, but they are not intended to limit it:
[0016] (1) Ashless dispersants: alkenyl succinimides, alkenyl
succinimides modified with other organic compounds, and alkenyl
succinimides modified with boric acid, alkenyl succinic ester.
[0017] (2) Oxidation inhibitors: (a) Phenol type oxidation
inhibitors: 4,4'-methylene bis (2,6-di-tert-butylphenol),
4,4'-bis(2,6-di-tert-butylphenol),
4,4'-bis(2-methyl-6-tert-butylphenol), 2,2'-methylene
bis(4-methyl-6-tert-butyl-phenol), 4,4'-butyl
idenebis(3-methyl-6-tert-butylphenol),
4,4'-isopropyl-idenebis(2,6-di-tert-butylphenol),
2,2'-methylene-bis(4-methyl-6-nonylphenol),
2,2'-isobutylidene-bis(4,6dimethyl-phenol), 2,2'-methylenebis
(4-methyl-6-cyclohexylphenol), 2,6-di-tert-butyl4-methyl-phenol,
2,6-di-tert-butyl4-ethylphenol, 2,4-dimethyl-6-tert-butyl-phenol,
2,6-di-tert-4-(N,N'-dimethyl-aminomethylphenol),
4,4'-thiobis(2-methyl-6-tert-butylphenol),
2,2'-thiobis(4-methyl-6-tert-butylphenol),
bis(3-methyl4-hydroxy-5-tert-butyl benzylysulfide, and bis
(3,5-di-tert-butyl4-hydroxybenzyl). (b) Diphenylamine type
oxidation inhibitor: alkylated diphenylamine,
phenyl-.alpha.-naphthylamine, and alkylated alpha-naphthylamine (c)
Other types: metal dithiocarbamate (e.g., zinc dithiocarbamate),
molybdenum oxysulfide succinimide complexes, and methylenebis
(dibutyl-dithiocarbamate). [0018] (3) Rust inhibitors (Anti-rust
agents) (a) Nonionic polyoxyethylene surface active agents:
polyoxyethylene lauryl ether, polyoxyethylene higher alcohol ether,
polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl
ether, polyoxyethylene octyl stearyl ether, polyoxyethylene oleyl
ether, polyoxyethylene sorbitol monostearate, polyoxyethylene
sorbitol mono-oleate, and polyethylene glycol monooleate. (b) Other
compounds: stearic acid and other fatty acids, dicarboxilic acids,
metal soaps, fatty acid amine salts, metal salts of heavy sulfonic
acid, partial carboxylic acid ester of polyhydric alcohol, and
phosphoric ester. [0019] (4) Demulsifiers: addition product of
alkylphenol and ethyleneoxide, poloxyethylene alkyl ether, and
polyoxyethylene sorbitan ester. [0020] (5) Extreme pressure agents
(EP agents): zinc dialkyldithiophosphate (aryl zinc, primary alkyl,
and secondary alkyl type), sulfurized oils, diphenyl sulfide,
methyl trichlorostearate, chlorinated naphthalene,
fluoroalkylpolysiloxane, and lead naphthenate. [0021] (6)
Multifunctional additives: sulfurized oxymolybdenum
dithiocarbamate, sulfurized oxymolybdenum organo phosphoro
dithioate, oxymolybdenum monoglyceride, oxymolybdenum diethylate
amide, amine-molybdenum complex compound, and sulfur-containing
molybdenym complex compound. [0022] (7) Viscosity index improvers:
polymethacrylate type polymers, ethylene-propylene copolymers,
styrene-isoprene copolymers, hydrated styrene-isoprene copolymers,
polyisobutylene, and dispersant type viscosity index improvers.
[0023] (8) Pour point depressants: polymethyl methacrylate. [0024]
(9) Foam Inhibitors: alkyl methacrylate polymers and dimethyl
silicone polymers. (11) Metal detergents: sulfurized or
unsulfurized alkyl or alkenyl phenates, alkyl or alkenyl aromatic
sulfonates, sulfurized or unsulfurized metal salts of multi-hydroxy
alkyl or alkenyl aromatic compounds, alkyl or alkenyl hydroxy
aromatic sulfonates, sulfurized or unsulfurized alkyl or alkenyl
naphthenates, metal salts of alkanoic acids, metal salts of an
alkyl or alkenyl multiacid, and chemical and physical mixtures
thereof. Non-limiting examples of suitable metals include alkali
metals, alkaline metals and transition metals. In some embodiments,
the metal is Ca, Mg, Ba, Sr, K, Na, Li or the like.
[0025] The base oil of the present invention is present in a "major
amount." A "major amount" of a base oil of lubricating viscosity
refers to a concentration of the oil within the lubricating oil
composition of at least about 40 wt %. In some embodiments, "a
major amount" of a base oil of lubricating viscosity refers to a
concentration of the oil within the lubricating oil composition of
at least about 50 wt %, at least about 60 wt %, at least about 70
wt %, at least about 80 wt %, or at least about 90 wt %.
[0026] To further illustrate the additive and the lubricating oil
compositions of this invention, the following non-limiting examples
are provided.
EXAMPLES
Example 1
Reaction Product of Oleylamine and Glycerol Carbonate
[0027] A 1 L glass reactor equipped with an agitator was charged
with oleylamine (473.96 g, 1.80 mole based on an amine value of 213
mg KOH/g; available from Akzo Nobel as Armeen.RTM. OLD) under a
nitrogen atmosphere and heated to 100.degree. C. Glycerol carbonate
(212.47 g, 1.80 mole; available from Huntsman as JEFFSOL.RTM.
glycerol carbonate) was added via an addition funnel over 2 hours.
The reaction mixture was heated at 100.degree. C. for an additional
5 h.
Example 2
Reaction Product of Oleylamine and Glycerol Carbonate
[0028] A 500 mL glass reactor equipped with an agitator was charged
with oleylamine (221.63 g, 0.84 mol based on an amine value of 213
mg KOH/g) under a nitrogen atmosphere and heated to 100.degree. C.
Glycerol carbonate (99.35 g, 0.84 mol) was added via an addition
funnel over several minutes. The reaction mixture was heated at
100.degree. C. for an additional 4 h.
Example 3
Reaction Product of Oleylamine and Glycerol Carbonate
[0029] A 500 mL glass reactor equipped with an agitator was charged
with oleylamine (217.53 g, 0.826 mole based on amine value of 213
mg KOH/g) under a nitrogen atmosphere and heated to 155.degree. C.
Glycerol carbonate (97.52 g, 0.826 mol) was added via a syringe
pump over 2 hours. The reaction mixture was heated at 160.degree.
C. for an additional 4 h.
Example 4
Reaction Product of Dodecylamine and Glycerol Carbonate
[0030] A 500 mL glass reactor equipped with an agitator was charged
with dodecylamine (281.35 g, 1.52 mol) under a nitrogen atmosphere
and heated to about 70.degree. C. Glycerol carbonate (179.24 g,
1.52 mol) was added via an addition funnel over several minutes.
The reaction mixture was heated at 70.degree. C. for an additional
2.5 h.
Example 5
Reaction Product of Oleylamine and Glycerol Carbonate
[0031] A 1 L glass reactor equipped with an agitator was charged
with oleylamine (462.61 g, 1.76 mol) under a nitrogen atmosphere
and heated to about 160.degree. C. Glycerol carbonate (207.38 g,
1.76 mol) was added via an addition funnel over several minutes.
The reaction mixture was heated at 160.degree. C. for an additional
4.5 h.
Example 6
Reaction Product of Oleylamine and Glycerol Carbonate
[0032] A 500 mL glass reactor equipped with an agitator was charged
with oleylamine (256.15 g, 0.97 mol based on amine value of 213 mg
KOH/g) under a nitrogen atmosphere and heated to about 70.degree.
C. The reactor was placed in a cooling water bath to remove the
heat of reaction and keep the reaction mixture temperature below
90.degree. C. Glycerol carbonate (114.83 g, 0.97 mol) was added via
an addition funnel over several minutes. The reaction mixture was
heated at 70.degree. C. for approximately an additional 3 h.
Example 7
Reaction Product of Oleylamine and Ethylene Carbonate
[0033] A 500 mL glass reactor equipped with an agitator was charged
with oleylamine (327.20 g, 1.24 mol based on amine value of 213 mg
KOH/g) under a nitrogen atmosphere and heated to about 70.degree.
C. The reactor was placed in a cooling water bath to remove the
heat of reaction and keep the reaction mixture temperature at about
70.degree. C. Ethylene carbonate (109.38 g, 1.24 mol) was added via
a syringe pump over several minutes. The reaction mixture was
heated at 70.degree. C. for approximately an additional 4 h.
Example 8
Reaction Product of 2-Ethylhexylamine and Ethylene Carbonate
[0034] A 500 mL glass reactor equipped with an agitator was charged
with oleylamine (164.06 g, 1.27 mol) under a nitrogen atmosphere
and heated to about 70.degree. C. The reactor was placed in a
cooling water bath to remove the heat of reaction and keep the
reaction mixture temperature at about 70.degree. C. Ethylene
carbonate (111.8 g, 1.27 mol) was added via a syringe pump over
several minutes. The reaction mixture was heated at 70.degree. C.
for approximately an additional 4 h.
Performance Examples
Anti-Wear Properties
[0035] The anti-wear properties of the following examples were
evaluated in a formulated baseline oil. This formulated oil
comprised a lubricating oil and additives in their typical amounts
for particular purpose; this included a zinc
dialkyldithiophosphate, a mixture of calcium-containing detergents,
a seal swell additive and a corrosion inhibitor.
[0036] The formulated baseline oil was then top-treated with either
0.3 wt. % of the glycerol carbamate of Example 2 or 0.3 wt % of
glycerol monooleate, a standard anti-wear additive. The three
formulations were then evaluated in the proprietary ZF-Standard V3,
S19-2 Wear Test Method available from ZF Friedrichshafen The
results are summarized in Table 1.
TABLE-US-00001 TABLE 1 ZF Standard Gear Wear Test Results
Formulation Weight Loss (mg) Baseline 577 Baseline + glycerol
monooleate 8 Baseline + Example 2 13
[0037] The lubricating oil composition containing glycerol
carbamate of Example 2 demonstrated comparable anti-wear properties
to the lubricating oil composition containing glycerol
monooleate.
Friction Modifier Properties
[0038] The frictional properties of the following examples were
evaluated in a formulated baseline oil. This formulated oil
comprised a 45N Group II lubricating oil and additives in their
typical amounts for particular purpose; this included 4.0 wt. %
succinimide 48.5 millimoles of a mixture of calcium containing
detergents, 7 millimoles of a mixture of primary and secondary zinc
dithiophosphates, 1.2 wt. % of an antioxidant, 0.5 wt. % of a
suflurized/molybdated succinimide complex, 0.3 wt. % of a pour
point depressant, 10 ppm of a foam inhibitor and 4.8 wt. % of a
viscosity index improver.
[0039] The formulated baseline oil was then top-treated with either
0.5 wt. % of Example 2 or 0.5 wt % of a borated glycerol
monooleate, a conventional friction modifier. The three
formulations were then evaluated in a proprietary mini traction
machine (MTM) friction test available from PCS Instruments. This
MTM friction test applies a certain load between a steel ball and
disk. The ball is rolling as well as sliding relative the disk. The
load, speed is designed into a profile that covers all the friction
conditions of a gasoline engine. While testing, the ball and the
disk are immersed in the lubricating oil to evaluate the
lubricating effect of this oil (meaning that the friction
coefficient between the ball and disk is measured under this
profile with the lubricating oil). The results are summarized in
Table 2.
TABLE-US-00002 TABLE 2 MTM Friction Test Results Formulation
Integration of Total Friction Baseline 139.67 Baseline + borated
glycerol monooleate 101.24 Baseline + Example 2 83.27 Baseline +
Example 8 83.36 Baseline + Example 7 109.62
[0040] The lubricating oil composition containing glycerol
carbamate demonstrated superior anti-friction properties to the
lubricating oil composition containing glycerol monooleate.
* * * * *