U.S. patent application number 10/574843 was filed with the patent office on 2007-02-22 for lubricating oil additive and lubricating oil composition.
This patent application is currently assigned to Idemitsu Kosan Co., Ltd.. Invention is credited to Toshihiko Ichihashi, Hiroaki Koshima, Izumi Terada, Nobuaki Watanabe, Shinichi Yanagi.
Application Number | 20070042918 10/574843 |
Document ID | / |
Family ID | 34431056 |
Filed Date | 2007-02-22 |
United States Patent
Application |
20070042918 |
Kind Code |
A1 |
Yanagi; Shinichi ; et
al. |
February 22, 2007 |
Lubricating oil additive and lubricating oil composition
Abstract
The present invention is directed to a lubricating oil additive
containing a reaction product of a succinimide compound and a
phosphorus atom-containing compound, and to a lubricating oil
composition containing a mineral oil and/or a synthetic base oil,
and the above lubricating oil additive.
Inventors: |
Yanagi; Shinichi; (Chiba,
JP) ; Koshima; Hiroaki; (Chiba, JP) ; Terada;
Izumi; (Chiba, JP) ; Ichihashi; Toshihiko;
(Chiba, JP) ; Watanabe; Nobuaki; (Chiba,
JP) |
Correspondence
Address: |
OBLON, SPIVAK, MCCLELLAND, MAIER & NEUSTADT, P.C.
1940 DUKE STREET
ALEXANDRIA
VA
22314
US
|
Assignee: |
Idemitsu Kosan Co., Ltd.
1-1, Marunouchi 3-chome Chiyoda-ku
Tokyo
JP
|
Family ID: |
34431056 |
Appl. No.: |
10/574843 |
Filed: |
October 4, 2004 |
PCT Filed: |
October 4, 2004 |
PCT NO: |
PCT/JP04/14976 |
371 Date: |
April 6, 2006 |
Current U.S.
Class: |
508/346 |
Current CPC
Class: |
C10M 2215/064 20130101;
C10M 2229/02 20130101; C10M 2219/106 20130101; C10M 2223/04
20130101; C10M 159/12 20130101; C10N 2040/04 20130101; C10M
2223/045 20130101; C10N 2040/042 20200501; C10M 2215/28 20130101;
C10M 2223/00 20130101; C10M 2223/049 20130101; C10M 159/123
20130101; C10M 2207/289 20130101; C10M 2207/026 20130101; C10M
2215/08 20130101; C10N 2040/08 20130101; C10N 2060/00 20130101;
C10M 2201/085 20130101; C10M 2203/1006 20130101; C10N 2020/04
20130101; C10M 2215/06 20130101; C10M 2219/044 20130101; C10M
2223/12 20130101; C10N 2030/00 20130101; C10M 2223/047 20130101;
C10M 2223/065 20130101; C10N 2030/06 20130101; C10M 2227/00
20130101; C10M 2209/084 20130101; C10N 2040/045 20200501; C10M
2215/28 20130101; C10N 2060/14 20130101; C10M 2215/28 20130101;
C10N 2060/14 20130101 |
Class at
Publication: |
508/346 |
International
Class: |
C10M 159/12 20060101
C10M159/12 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 9, 2003 |
JP |
2003-350600 |
Claims
1. A lubricating oil additive comprising a reaction product of a
succinimide compound and a phosphorus atom-containing compound.
2. A lubricating oil additive as recited in claim 1, wherein the
phosphorus atom-containing compound is at least one compound
selected from the group consisting of phosphorus sulfide, a phospho
sulfurized hydrocarbon compound, a phosphate ester, a phosphite
ester and a dithiophosphate ester.
3. A lubricating oil additive as recited in claim 2, wherein the
phospho sulfurized hydrocarbon compound has a structure in which
two alkyl groups are bonded to a phosphorus atom.
4. A lubricating oil additive as recited in claim 2, wherein the
phosphate ester, phosphite ester and dithiophosphate ester are each
a diester.
5. A lubricating oil additive as recited in claim 2, wherein the
alkyl group introduced into the phosphorus atom-containing
hydrocarbon compound is an alkyl group which has 2 to 25 carbon
atoms and which may have an ether bond and/or a thioether bond.
6. A lubricating oil composition characterized by comprising a
mineral oil and/or a synthetic base oil, and a lubricating oil
additive according to claim 1.
7. A lubricating oil composition as recited in claim 6, wherein the
composition is used for a transmission having a wet clutch or a wet
brake.
8. A lubricating oil composition as recited in claim 6, wherein the
composition is an automatic transmission fluid or a continuously
variable transmission fluid.
Description
TECHNICAL FIELD
[0001] The present invention relates to a lubricating oil additive
and to a lubricating oil composition. More specifically, the
present invention is directed to a lubricating oil additive which
can afford a lubricating oil composition, such as an automatic
transmission fluid or a continuously variable transmission fluid,
having a particularly high wet friction material torque capacity
and excellent .mu. (friction coefficient)-V (sliding velocity)
performances, and to a lubricating oil composition containing such
a lubricating oil additive and having the above properties.
BACKGROUND ART
[0002] In recent years, there has been an increasing demand for a
reduction of fuel consumption of automobiles for the purpose of
reducing the discharge amount of carbon dioxide in view of the
global environmental problems.
[0003] In particular, in transmissions, an improvement of power
transmission efficiency is going to be more demanded than ever and,
thus, a high torque capacity is required for a lubricating oil
which is one of the important constituent components thereof.
[0004] On the other hand, as an effective means to improve the
power transmission efficiency, use has been recently made of a
lock-up clutch, which is effective in improving the fuel
consumption, in automatic transmission and continuously variable
transmission of automobiles.
[0005] In this mechanism, the transmission is built in a torque
converter.
[0006] Such a lock-up clutch has a function to transmit the driving
power from an engine directly to the transmission according to the
running conditions. By shifting between the torque converter drive
and the direct drive at proper timings, the efficiency of the
torque converter can be improved.
[0007] Hitherto, use has been proposed of a phosphate ester, a
fatty acid ester, a fatty amide or the like as a friction modifier
for an automatic transmission fluid or a continuously variable
transmission fluid.
[0008] The incorporation of such a friction modifier, however, has
a defect that the friction coefficient in a low velocity slip area
of the lock-up clutch part is reduced and the friction coefficient
of a wet clutch is considerably reduced, so that a sufficient
transmission torque capacity cannot be ensured.
[0009] For this reason, a metal-type detergent such as calcium
sulfonate has been incorporated for the purpose of improving the
transmission torque capacity.
[0010] The addition of these substances, however, causes a problem
that the friction material is clogged upon use for a long period of
time so that the friction coefficient is reduced and the friction
characteristics, such as .mu.-V performances of the lock-up clutch
part, are deteriorated.
[0011] To cope with this problem, a lubricating oil composition
containing a bisimide and a monoimide having a hydrocarbyl group
with 8 to 30 carbon atoms is disclosed (for example, see
JP-A-2002-105478) as a composition exhibiting both high torque
capacity of a wet clutch and good transmission performances while
maintaining the shudder vibration preventing performance in a low
speed range.
[0012] A lubricating oil composition containing a bisimide compound
having a hydrocarbyl group with 8 to 30 carbon atoms and a
boron-modified ashless dispersant is disclosed (for example, see
JP-A-2001-288489) as a composition capable of maintaining shudder
vibration preventing performance in a low speed range and of
preventing delamination in the clutch.
[0013] With such lubricating oil compositions, however, a problem
has been pointed out that a sufficient torque capacity cannot be
ensured.
[0014] With the foregoing background in view, there is a demand, in
the field of automatic transmission fluids and continuously
variable transmission fluids, for the development of a technique
for satisfying required friction performances of a wet friction
material, particularly a technique for increasing the friction
coefficient of a wet clutch, while maintaining freedom of metal
components or maintaining a metal content at a low level.
[0015] The present invention has been made in the above situation
and has as its object the provision of a lubricating oil additive
which can afford a lubricating oil composition, such as an
automatic transmission fluid or a continuously variable
transmission fluid, having a particularly high wet friction
material torque capacity and excellent .mu.-V performances, and of
a lubricating oil composition containing such a lubricating oil
additive and having the above properties.
DISCLOSURE OF THE INVENTION
[0016] The present inventors have made an intensive study to
achieve the foregoing objects and, as a result, have found that a
reaction product of a succinimide compound and a phosphorus
atom-containing compound can serve as a lubricating oil additive
meeting with the objects.
[0017] The present invention has been completed on the basis of
such a finding.
[0018] Thus, the present invention provides: [0019] (1) a
lubricating oil additive comprising a reaction product of a
succinimide compound and a phosphorus atom-containing compound;
[0020] (2) a lubricating oil additive of (1) above, wherein the
phosphorus atom-containing compound is at least one compound
selected from the group consisting of phosphorus sulfide, a phospho
sulfurized hydrocarbon compound, a phosphate ester, a phosphite
ester and a dithiophosphate ester; [0021] (3) a lubricating oil
additive of (2) above, wherein the phospho sulfurized hydrocarbon
compound has a structure in which two alkyl groups are bonded to a
phosphorus atom; [0022] (4) a lubricating oil additive of (2)
above, wherein the phosphate ester, phosphite ester and
dithiophosphate ester are each a diester; [0023] (5) a lubricating
oil additive of any one of (2) to (4) above, wherein the alkyl
group introduced into the phosphorus atom-containing compound is an
alkyl group which has 2 to 25 carbon atoms and which may have an
ether bond and/or a thioether bond; [0024] (6) a lubricating oil
composition characterized by comprising a mineral oil and/or a
synthetic base oil, and a lubricating oil additive according to any
one of (1) to (5) above; [0025] (7) a lubricating oil composition
of (6) above, wherein the composition is used for a transmission
having a wet clutch or a wet brake; and [0026] (8) a lubricating
oil composition of (6) above, wherein the composition is an
automatic transmission fluid or a continuously variable
transmission fluid.
[0027] According to the present invention, there can be provided a
lubricating oil additive which can afford a lubricating oil
composition, such as an automatic transmission fluid or a
continuously variable transmission fluid, having a particularly
high wet friction material torque capacity and excellent .mu.-V
performances, and a lubricating oil composition containing such a
lubricating oil additive and having the above properties.
BEST MODE FOR CARRYING OUT THE INVENTION
[0028] The lubricating oil additive of the present invention is a
reaction product of (A) a succinimide compound and (B) a phosphorus
atom-containing compound.
[0029] In the lubricating oil additive of the present invention,
the succinimide compound used as the raw material (A) may be a
boron-free succinimide compound or a boron-containing succinimide
compound.
[0030] The boron-free succinimide compound may be, for example, a
succinimide represented by the general formula (I): ##STR1## or by
the general formula (II): ##STR2##
[0031] In the general formulas (I) and (II), R.sup.1 and R.sup.3
each represent an alkyl group or an alkenyl group having 5 to 350
carbon atoms and R.sup.4 represents hydrogen, or an alkyl group or
an alkenyl group having 5 to 350 carbon atoms.
[0032] R.sup.3 and R.sup.4 may be the same with or different from
each other.
[0033] R.sup.2, R.sup.5 and R.sup.6 each represent a divalent
organic group and R.sup.5 and R.sup.6 may be the same with or
different from each other.
[0034] Represented by m is an integer of 1 to 10 and by n is an
integer of 1 to 10.
[0035] The above alkyl or alkenyl group is preferably a polyalkenyl
group, particularly a polybutenyl group or a polyisobutenyl
group.
[0036] The succinimide represented by the general formula (I) or
(II) may be produced by reacting an alkenyl or alkyl succinic acid
or alkenyl or alkyl succinic anhydride with a corresponding
amine.
[0037] As the amine, there may be mentioned, for example,
ethylenediamine, propanediamine, butanediamine,
N-methyl-1,3-propanediamine, N,N-dimethyl-1,3-propanediamine and a
polyalkylenepolyamine such as diethylenetriamine,
triethylenetetramine, aminoethylpiperazine or
tetraethylenepentamine.
[0038] The boron-containing succinimide compound may be obtained by
reacting the boron-free succinimide compound with a
boron-containing compound generally at a temperature of 50 to
250.degree. C., preferably 100 to 200.degree. C.
[0039] As the boron-containing compound, there may be used at least
one compound selected from a boron oxide, a boron halide, boric
acid, boric anhydride, a borate ester, etc.
[0040] In the present invention, as the raw material (A), the
above-described succinimide compounds may be used singly or in
combination with two or more thereof.
[0041] As the phosphorus atom-containing compound used as the raw
material (B), there may be mentioned, for example, a phosphorus
sulfide, a phospho sulfurized hydrocarbon compound, a phosphate
ester, a phosphite ester and a dithiophosphate ester.
[0042] The alkyl group or groups incorporated into the phosphorus
atom-containing compound may be linear or branched and may contain
a cyclic structure. Further, an ether bond and/or a thioether bond
may be also contained in the alkyl group or groups.
[0043] As the phosphorus sulfide, there may be mentioned
P.sub.2S.sub.3, P.sub.2S.sub.5, P.sub.4S.sub.7 and P.sub.4S.sub.10.
Above all, P.sub.2S.sub.5 is preferred.
[0044] As the phospho sulfurized hydrocarbon compound, there may be
used various compounds. Phospho sulfurized hydrocarbon compounds
having a structure in which two alkyl groups are bonded to a
phosphorus atom are preferable.
[0045] Such compounds may include reaction products of an olefin
and a phosphorus sulfide.
[0046] For example, a phospho sulfurized hydrocarbon compound may
be obtainable by using propylene, butene, isobutylene, a polymer or
copolymer thereof, decene, cetene, octadecene, a terpene (such as
pinene), vinylnorbornene or camphene as an olefin and
P.sub.2S.sub.3, P.sub.2S.sub.5, P.sub.4S.sub.7 or P.sub.4S.sub.10
as a phosphorus sulfide, and by reacting them at a temperature of
about 100 to 300.degree. C. under a stream of nitrogen gas.
[0047] In this case, as raw materials, the particularly preferred
olefin is .alpha.-pinene and the preferred phosphorus sulfide is
P.sub.2S.sub.5.
[0048] It is preferred that the phosphate ester, phosphite ester
and dithiophosphate ester be each a diester.
[0049] As the preferable phosphate ester, there may be mentioned an
acidic phosphate ester represented by the general formula (III):
##STR3## wherein R.sup.7 and R.sup.8 each represent a hydrocarbyl
group having 1 to 20 carbon atoms. Specifically, R.sup.7 and
R.sup.8 may be a linear or branched alkyl group having 1 to 20
carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a
linear or branched alkenyl group having 2 to 20 carbon atoms, an
aryl group having 6 to 20 carbon atoms or an aralkyl group having 7
to 20 carbon atoms.
[0050] Examples of the alkyl group having 1 to 20 carbon atoms
include a methyl group, an ethyl group, a n-propyl group, an
isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl
group, a tert-butyl group, a pentyl group, a hexyl group, an octyl
group, a 2-ethylhexyl group, a decyl group, a dodecyl group, a
tetradecyl group, a hexadecyl group, an octadecyl group and an
eicosyl group.
[0051] Examples of the cycloalkyl group having 3 to 20 carbon atoms
include a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl
group and a cyclooctyl group.
[0052] Examples of the alkenyl group having 2 to 20 carbon atoms
include an allyl group, a propenyl group, a butenyl group, an
octenyl group, a decenyl group and an oleyl group.
[0053] Examples of the aryl group having 6 to 20 carbon atoms
include a phenyl group, a tolyl group, a xylyl group and a naphthyl
group. Examples of the aralkyl group having 7 to 20 carbon atoms
include a benzyl group, a phenethyl group and a naphthylmethyl
group.
[0054] The hydrocarbyl group having 1 to 20 carbon atoms may be
interrupted by one or more oxygen atoms and/or sulfur atoms.
[0055] Namely, the main chain may contain at least one ether bond
or thioether bond or contain both ether and thioether bonds.
[0056] Examples of such a hydrocarbyl group include a
hexyloxymethyl group, a hexyloxyethyl group, an octyloxymethyl
group, an octyloxyethyl group, a dodecyloxymethyl group, a
dodecyloxyethyl group, a hexadecyloxymethyl group, a
hexadecyloxyethyl group, a hexylthiomethyl group, a hexylthioethyl
group, an octylthiomethyl group, an octylthioethyl group, a
dodecylthiomethyl group, a dodecylthioethyl group, a
hexadecylthiomethyl group and a hexadecylthioethyl group.
[0057] As the acidic phosphate ester represented by the general
formula (III), there may be mentioned, for example, dihexyl
phosphate, dioctyl phosphate, di(2-ethylhexyl) phosphate, didodecyl
phosphate, dihexadecyl phosphate, di(hexylthioethyl) phosphate,
di(octylthioethyl) phosphate, di(dodecylthioethyl) phosphate,
di(hexadecylthioethyl) phosphate, dioctenyl phosphate, dioleyl
phosphate, dicyclohexyl phosphate, diphenyl phosphate, ditolyl
phosphate, dibenzyl phosphate and diphenethyl phosphate.
[0058] As the preferred phosphite ester, there may be mentioned an
acidic phosphite ester represented by the general formula (IV):
##STR4## wherein R.sup.7 and R.sup.8 are as defined above.
[0059] As the acidic phosphite ester represented by the general
formula (IV), there may be mentioned, for example, dihexyl hydrogen
phosphite, dioctyl hydrogen phosphite, di(2-ethylhexyl) hydrogen
phosphite, didodecyl hydrogen phosphite, dihexadecyl hydrogen
phosphite, di(hexylthioethyl) hydrogen phosphite,
di(octylthioethyl) hydrogen phosphite, di(dodecylthioethyl)
hydrogen phosphite, di(hexadecylthioethyl) hydrogen phosphite,
dioctenyl hydrogen phosphite, dioleyl hydrogen phosphite,
dicyclohexyl hydrogen phosphite, diphenyl hydrogen phosphite,
ditolyl hydrogen phosphite, dibenzyl hydrogen phosphite and
diphenethyl hydrogen phosphite.
[0060] As the preferred dithiophosphate ester, there may be
mentioned a dithiophosphate ester represented by the general
formula (V): ##STR5## wherein R.sup.7 and R.sup.8 are as defined
above.
[0061] As the dithiophosphate ester represented by the general
formula (V), there may be mentioned, for example, dihexyl
dithiophosphate, dioctyl dithiophosphate, di(2-ethylhexyl)
dithiophosphate, didodecyl dithiophosphate, dihexadecyl
dithiophosphate, di(hexylthioethyl) dithiophosphate,
di(octylthioethyl) dithiophosphate, di(dodecylthioethyl)
dithiophosphate, di(hexadecylthioethyl) dithiophosphate, dioctenyl
dithiophosphate, dioleyl dithiophosphate, dicyclohexyl
dithiophosphate, diphenyl dithiophosphate, ditolyl dithiophosphate,
dibenzyl dithiophosphate and diphenethyl dithiophosphate.
[0062] In the present invention, as the raw material (B), the
above-described phosphorus atom-containing compounds may be used
singly or in combination with two or more thereof.
[0063] The lubricating oil additive of the present invention is a
reaction product obtained by reacting the above-described raw
material (A) with raw material (B) in a molar ratio of preferably
1:10 to 10:1, more preferably 1:3 to 3:1. By using the raw material
(A) and raw material (B) in the above proportion range, a
lubricating oil additive having the desired performance may be
obtained.
[0064] The reaction may be carried out at a temperature of
generally about 50 to 250.degree. C., preferably 100 to 200.degree.
C.
[0065] In this case, an organic solvent such as a hydrocarbon
compound may be used, if necessary.
[0066] The lubricating oil additive of the present invention thus
obtained can afford a lubricating oil composition, such as an
automatic transmission fluid or a continuously variable
transmission fluid, having a particularly high wet friction
material torque capacity and excellent .mu.-V performances.
[0067] The lubricating oil composition of the present invention
comprises a mineral oil and/or a synthetic base oil, and the
above-described lubricating oil additive. The content of the
lubricating oil additive in the lubricating oil composition is
preferably 0.01 to 50% by mass, more preferably 0.1 to 20% by mass,
from the standpoint of capability of effectively showing the above
effects.
[0068] As the base oil used in the composition of the present
invention, both mineral oil and synthetic oil may be used.
[0069] As the mineral oil, any of various conventionally known
mineral oils may be used and there may be mentioned, for example, a
paraffinic mineral oil, an intermediate mineral oil and a
naphthenic mineral oil. Specific examples of the mineral oil
include solvent-refined or hydrogen-refined light neutral oil,
medium neutral oil, heavy neutral oil or bright stock and the
like.
[0070] As the synthetic oil, any of various conventionally known
synthetic oils may be used and there may be used, for example,
poly(.alpha.-olefin) (including a copolymer of .alpha.-olefin),
polybutene, a polyol ester, an ester of a dibasic acid, a phosphate
ester, a polyphenyl ether, an alkylbenzene, an alkylnaphthalene, a
polyoxyalkylene glycol, neopentyl glycol, silicone oil, trimethylol
propane, pentaerythritol and, further, a hindered ester.
[0071] These base oils may be used singly or in combination of two
or more thereof. A mineral oil and a synthetic oil may be also used
in combination.
[0072] It is preferred that the base oil have a kinematic viscosity
at 100.degree. C. of 1 to 30 mm.sup.2/s and % C.sub.A of 20% or
less.
[0073] When the kinematic viscosity is in the above range, it is
possible to sufficiently reduce the friction in a sliding part,
such as a gear bearing or a clutch, of an automatic transmission.
Additionally, the low-temperature characteristics are good.
[0074] The kinematic viscosity at 100.degree. C. is more preferably
2 to 20 mm.sup.2/s, particularly preferably 3 to 10 mm.sup.2/s.
[0075] When the % C.sub.A is 20% or less, the low-temperature
characteristics are good. The % C.sub.A is particularly preferably
10% or less.
[0076] Various additives other than the lubricating oil additive of
the present invention may be incorporated, singly or in combination
of a plurality thereof, into the lubricating oil composition of the
present invention for the purpose of further improving the
performance thereof. Representatives of such additives include an
ashless dispersant, a metallic detergent, a friction modifier, a
viscosity index improver, an extreme pressure additive, a corrosion
inhibitor, an antifoaming agent and a colorant. The lubricating oil
additive of the present invention would not hinder the effects of
such other additives.
[0077] The lubricating oil composition of the present invention
thus formulated is suited as an automatic transmission fluid or a
continuously variable transmission fluid having a high wet friction
material torque capacity and excellent .mu.-V performances and may
be also used as a lubricating oil for construction or agricultural
machines equipped with a transmission having a wet clutch or a wet
brake, manual transmissions, motorcycle gasoline engines, diesel
engines, gas engines and shock absorbers.
[0078] The present invention will be next described by Examples but
is not limited thereto in any way.
[0079] In Examples, the performance of the lubricating oil
composition was evaluated according to the following method.
(1) Evaluation of Wet Friction Material Torque Capacity and .mu.-V
Performances:
[0080] Using a Low Velocity Friction Apparatus, the test was
carried out under the conditions shown below to evaluate the wet
friction material torque capacity in terms of a friction
coefficient at 250 rpm (.mu.250). The .mu.-V performances were
evaluated in terms of .mu. ratio (.mu.50/.mu.1).
[0081] The higher the .mu.250 value is, the higher the torque
capacity is. A .mu.50/.mu.1 value of greater than 1 is regarded as
being good.
[0082] Designated as .mu.1 is a friction coefficient at 1 rpm,
while as .mu.50 is a friction coefficient at 50 rpm.
Test conditions:
[0083] Friction material: commercially available cellulose wet
paper material and steel plate
[0084] Test temperature: 120.degree. C.
[0085] Surface pressure: 0.98 MPa
[0086] Measurement: 1 to 300 rpm, stepwise
EXAMPLE 1
(1) Preparation of Lubricating Oil Additive
[0087] In a 500 mL separable flask, 0.12 mole of borated
succinimide (mono-type, alkyl group: polybutene having an average
molecular weight of 960, boron content: 1.0% by mass; unless
otherwise specifically noted, similar succinimide was used in the
following examples) and 0.17 mole of dioleyl hydrogen phosphite
were charged and reacted at 150.degree. C. for 6 hours under a
stream of nitrogen gas. The water by-produced was removed in vacuo
at 150.degree. C., thereby obtaining a lubricating oil additive (a)
which was a reaction product of borated succinimide and dioleyl
hydrogen phosphite.
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0088] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 87.8% by mass of the
mineral oil and 12.2% by mass of the lubricating oil additive (a)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (a) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 2
(1) Preparation of Lubricating Oil Additive
[0089] A lubricating oil additive (b) was prepared in the same
manner as that described in Example 1-(1) except that
di(2-ethylhexyl) hydrogen phosphite was substituted for dioleyl
hydrogen phosphite in Example 1-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0090] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 91.7% by mass of the
mineral oil and 8.3% by mass of the lubricating oil additive (b)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (b) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 3
(1) Preparation of Lubricating Oil Additive
[0091] A lubricating oil additive (c) was prepared in the same
manner as that described in Example 1-(1) except that
di(octylthioethyl) hydrogen phosphite was substituted for dioleyl
hydrogen phosphite in Example 1-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0092] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 90.0% by mass of the
mineral oil and 10.0% by mass of the lubricating oil additive (c)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (c) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 4
(1) Preparation of Lubricating Oil Additive
[0093] A lubricating oil additive (d) was prepared in the same
manner as that described in Example 1-(1) except that a phosphorus
compound represented by the following formula ##STR6## was
substituted for dioleyl hydrogen phosphite in Example 1-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0094] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 90.6% by mass of the
mineral oil and 9.4% by mass of the lubricating oil additive (d)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (d) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 5
(1) Preparation of Lubricating Oil Additive
[0095] In a 500 mL separable flask, 0.12 mole of borated
succinimide (boron content: 0.4% by mass) and 0.06 mole of phospho
sulfurized pinene were charged and reacted at 170.degree. C. for 8
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (e) which was a reaction
product of borated succinimide and phospho sulfurized pinene.
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0096] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 89.7% by mass of the
mineral oil and 10.3% by mass of the lubricating oil additive (d)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (e) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 6
(1) Preparation of Lubricating Oil Additive
[0097] A lubricating oil additive (f) was prepared in the same
manner as that described in Example 5-(1) except that
di(2-ethylhexyl) dithiophosphate was substituted for phospho
sulfurized pinene in Example 5-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0098] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 92.1% by mass of the
mineral oil and 7.9% by mass of the lubricating oil additive (f)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (f) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 7
(1) Preparation of Lubricating Oil Additive
[0099] In a 500 mL separable flask, 0.12 mole of borated
succinimide (boron content: 1.0% by mass) and 0.04 mole of
diphosphorus pentasulfide were charged and reacted at 170.degree.
C. for 8 hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (g) which was a reaction
product of borated succinimide and diphosphorus pentasulfide.
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0100] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 91.2% by mass of the
mineral oil and 8.8% by mass of the lubricating oil additive (g)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (g) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 8
(1) Preparation of Lubricating Oil Additive
[0101] A lubricating oil additive (h) was prepared in the same
manner as that described in Example 5-(1) except that borated
succinimide (boron content: 0.6% by mass) was substituted for
borated succinimide (boron content: 0.4% by mass) in Example
5-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0102] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 92.5% by mass of the
mineral oil and 7.5% by mass of the lubricating oil additive (h)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (h) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 9
(1) Preparation of Lubricating Oil Additive
[0103] In a 200 mL separable flask, 50 g of commercially available
borated succinimide (boron content: 2.0% by mass) and 5.5 g of
phospho sulfurized pinene were charged and reacted at 170.degree.
C. for 8 hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (i).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0104] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 93.2% by mass of the
mineral oil and 6.8% by mass of the lubricating oil additive (i)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (i) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 10
(1) Preparation of Lubricating Oil Additive
[0105] In a 300 mL four-necked flask, a solution of 0.035 mole of
borated succinimide (boron content: 1.0% by mass) in 70 mL of
xylene was prepared, to which a solution of 0.023 mole of
diphosphorus pentasulfide in 70 mL of xylene was added at
100.degree. C. under a stream of nitrogen gas.
[0106] The mixture was reacted at 160.degree. C. for 6 hours under
reflux. Thereafter, xylene was removed by distillation, thereby
obtaining a lubricating oil additive (j) which was a reaction
product of borated succinimide and diphosphorus pentasulfide.
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0107] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 92.5% by mass of the
mineral oil and 7.5% by mass of the lubricating oil additive (j)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (j) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1.
EXAMPLE 11
(1) Preparation of Lubricating Oil Additive
[0108] A lubricating oil additive (k) was prepared in the same
manner as that described in Example 10-(1) except that borated
succinimide (boron content: 0.6% by mass) was substituted for
borated succinimide (boron content: 1.0% by mass) in Example
10-(1).
(2) Preparation of Lubricating Oil Composition and Evaluation of
its Performance
[0109] Using a mineral oil corresponding to 150 neutral as a base
oil, a lubricating oil composition containing 92.1% by mass of the
mineral oil and 7.9% by mass of the lubricating oil additive (k)
obtained in (1) above was prepared, so that the content of nitrogen
derived from the lubricating oil additive (k) was 1,500 ppm by
mass. The performance of the composition was evaluated. The results
are shown in Table 1. TABLE-US-00001 TABLE 1 Lubricating
Composition Oil Lubricating Evaluation of oil Performance Mineral
oil additive Torque (% by (% by capacity .mu. ratio mass) Kind
mass) [.mu.250] [.mu.50/.mu.1] Example 1 87.8 (a) 12.2 0.164 1.293
Example 2 91.7 (b) 8.3 0.173 1.219 Example 3 90.0 (c) 10.0 0.163
1.197 Example 4 90.6 (d) 9.4 0.166 1.197 Example 5 89.7 (e) 10.3
0.188 1.105 Example 6 92.1 (f) 7.9 0.176 1.267 Example 7 91.2 (g)
8.8 0.180 1.128 Example 8 92.5 (h) 7.5 0.190 1.108 Example 9 93.2
(i) 6.8 0.186 1.046 Example 10 92.5 (j) 7.5 0.193 1.066 Example 11
92.1 (k) 7.9 0.183 1.058
COMPARATIVE EXAMPLES 1 TO 5
[0110] Using a mineral oil corresponding to 150 neutral as a base
oil and an additive (1) or additives (1) and (2) shown in Table 2
as a lubricating oil additive, lubricating oil compositions having
the formulations shown in Table 3 were prepared, so that the
content of nitrogen derived from the additive (1) was 1,500 ppm by
mass. The performance of each of the compositions was evaluated.
The results are shown in Table 3. TABLE-US-00002 TABLE 2 Additive 1
Additive 2 Comparative Monosuccinimide -- Example 1 Comparative
Bissuccinimide -- Example 2 Comparative Borated succinimide --
Example 3 (boron content: 2.0% by mass) Comparative Borated
succinimide Dioleyl hydrogen Example 4 (boron content: 1.0% by
mass) phosphite Comparative Borated succinimide Phospho sulfurized
Example 5 (boron content: 1.0% by mass) pinene
[0111] TABLE-US-00003 TABLE 3 Lubricating Oil Composition
Evaluation of Additive Additive Performance Mineral oil (1) (2)
Torque (% by (% by (% by capacity .mu. ratio mass) mass) mass)
[.mu.250] [.mu.50/.mu.1] Comparative 92.0 8.0 -- 0.129 0.960
Example 1 Comparative 84.7 15.3 -- 0.114 0.925 Example 2
Comparative 93.2 6.8 -- 0.155 0.966 Example 3 Comparative 89.9 7.5
2.6 0.147 1.545 Example 4 Comparative 91.7 7.5 0.8 0.159 1.067
Example 5
[0112] As will be evident from the above results, the lubricating
oil compositions of Examples 1 to 11 containing the lubricating oil
additive of the present invention can maintain the transmission
torque capacity at a high level and show a .mu. ratio
(.mu.50/.mu.1) of greater than 1.
[0113] In the case of the lubricating oil compositions containing
only an imide dispersant (Comparative Examples 1 to 3), on the
other hand, the transmission torque capacity is insufficient and
the .mu. ratio is less than 1.
[0114] In the case of the lubricating oil compositions which
contain borated imide and a phosphorus compound rather than a
reaction product of them (Comparative Examples 4 and 5), the
transmission torque capacity is insufficient.
(2) Evaluation as Automatic Transmission Fluid Composition
(LVFA)
[0115] Automatic transmission fluid compositions which contained
lubricating oil additives (the reaction products of borated
succinimide and phospho sulfurized pinene, giving the highest .mu.d
value in Examples 1 to 11) and which were compounded with various
additives shown in Table 4 (polymethacrylate, calcium sulfonate,
isostearamide and oleyl glyceride; numerals are % by mass) were
prepared and evaluated for the purpose of confirming the
performance as automatic transmission fluid compositions.
[0116] As other additives, the automatic transmission fluid
compositions were further compounded with 1.1% by mass of a mixture
containing 30% by mass of a phenol antioxidant, 30% by mass of an
amine antioxidant, 30% by mass of a sulfur antioxidant, 3% by mass
of a thiadiazole copper inactivation agent and 10% by mass of a
silicone antifoaming agent.
[0117] The automatic transmission fluid compositions were each
compounded with a mixture, as a base oil, containing 12.5% by mass
of a mineral oil corresponding to 60 neutral and the balance of a
mineral oil corresponding to 100 neutral.
EXAMPLE 12
(1) Preparation of Lubricating Oil Additive
[0118] In a 500 mL separable flask, 0.12 mole of borated
succinimide (boron content: 0.4% by mass) and 0.06 mole of phospho
sulfurized pinene were charged and reacted at 170.degree. C. for 8
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (I) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0119] An automatic transmission fluid composition containing the
lubricating oil additive (I) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (I) was 1,500 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 13
(1) Preparation of Lubricating Oil Additive
[0120] In a 200 mL separable flask, 0.06 mole of borated
succinimide (boron content: 0.6% by mass) and 0.03 mole of phospho
sulfurized pinene were charged and reacted at 170.degree. C. for 8
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (m) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0121] An automatic transmission fluid composition containing the
lubricating oil additive (m) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (m) was 1,500 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 14
(1) Preparation of Lubricating Oil Additive
[0122] A lubricating oil additive (n) was prepared in the same
manner as that described in Example 13-(1) except that borated
succinimide (boron content: 1.0% by mass) was substituted for
borated succinimide (boron content: 0.6% by mass) in Example
13-(1).
(2) Evaluation of Performance
[0123] An automatic transmission fluid composition containing the
lubricating oil additive (n) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (n) was 1,500 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 15
(1) Preparation of Lubricating Oil Additive
[0124] In a 200 mL separable flask, 0.031 mole of borated
succinimide (boron content: 3.0% by mass) and 0.023 mole of phospho
sulfurized pinene were charged and reacted at 180.degree. C. for 6
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (o) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0125] An automatic transmission fluid composition containing the
lubricating oil additive (o) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (o) was 750 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 16
(1) Preparation of Lubricating Oil Additive
[0126] In a 200 mL separable flask, 0.033 mole of borated
succinimide (boron content: 2.8% by mass) and 0.020 mole of phospho
sulfurized pinene were charged and reacted at 180.degree. C. for 6
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (p) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0127] An automatic transmission fluid composition containing the
lubricating oil additive (p) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (p) was 750 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 17
(1) Preparation of Lubricating Oil Additive
[0128] In a 200 mL separable flask, 0.034 mole of borated
succinimide (boron content: 2.0% by mass) and 0.017 mole of phospho
sulfurized pinene were charged and reacted at 180.degree. C. for 6
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (q) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0129] An automatic transmission fluid composition containing the
lubricating oil additive (q) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (q) was 750 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 18
(1) Preparation of Lubricating Oil Additive
[0130] In a 200 mL separable flask, 0.033 mole of borated
succinimide (boron content: 2.0% by mass) and 0.020 mole of phospho
sulfurized pinene were charged and reacted at 180.degree. C. for 6
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (r) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0131] An automatic transmission fluid composition containing the
lubricating oil additive (r) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (r) was 750 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
EXAMPLE 19
(1) Preparation of Lubricating Oil Additive
[0132] In a 200 mL separable flask, 0.034 mole of borated
succinimide (boron content: 2.4% by mass) and 0.017 mole of phospho
sulfurized pinene were charged and reacted at 180.degree. C. for 6
hours under a stream of nitrogen gas. The hydrogen sulfide
by-produced was removed in vacuo at 150.degree. C., thereby
obtaining a lubricating oil additive (s) which was a reaction
product of borated succinimide and phosphor sulfurized pinene.
(2) Evaluation of Performance
[0133] An automatic transmission fluid composition containing the
lubricating oil additive (s) obtained in (1) above was prepared, so
that the content of nitrogen derived from the lubricating oil
additive (s) was 750 ppm by mass. The performance of the
composition was evaluated. The results are shown in Table 4.
COMPARATIVE EXAMPLE 6
[0134] An automatic transmission fluid composition containing
tricresyl phosphate, as a phosphor source, and borated succinimide
in lieu of the additive of Examples 12 to 19 was prepared. The
performance of the composition was evaluated.
[0135] The amount of nitrogen contained in the lubricating oil
composition was 800 ppm by mass. The results are shown in Table 4.
TABLE-US-00004 TABLE 4 Comparative Automatic Transmission Fluid
Example Example Composition 12 13 14 15 16 17 18 19 6 Base 100
Neutral mineral oil balance balance balance balance balance balance
balance balance balance oil 60 Neutral mineral oil 12.5 12.5 12.5
12.5 12.5 12.5 12.5 12.5 12.5 Polymethacrylate 8.5 8.5 8.5 8.5 8.5
8.5 8.5 8.5 8.5 Calcium sulfonate 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5
1.5 Isostearamide 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Oleyl
glyceride 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Borated imide -- --
-- -- -- -- -- -- 1.5 Tricresyl phosphate -- -- -- -- -- -- -- --
0.3 Additive (l) 7.9 -- -- -- -- -- -- -- -- Additive (m) -- 7.9 --
-- -- -- -- -- -- Additive (n) -- -- 7.9 -- -- -- -- -- -- Additive
(o) -- -- -- 3.1 -- -- -- -- -- Additive (p) -- -- -- -- 3.8 -- --
-- -- Additive (q) -- -- -- -- -- 4.7 -- -- -- Additive (r) -- --
-- -- -- -- 3.8 -- -- Additive (s) -- -- -- -- -- -- -- 4.7 --
Other additive (*) 1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1 Torque
Capacity [.mu.250] 0.156 0.174 0.167 0.166 0.169 0.170 0.170 0.173
0.146 .mu. Ratio [.mu.50/.mu.1] 1.133 1.208 1.156 1.273 1.275 1.232
1.323 1.274 1.306 (*) An antioxidant, a copper inactivation agent
and an antifoaming agent were compounded in a constant amount.
INDUSTRIAL APPLICABILITY
[0136] The lubricating oil additive of the present invention can
afford a lubricating oil composition, such as an automatic
transmission fluid or a continuously variable transmission fluid,
having a particularly high wet friction material torque capacity
and excellent .mu.-V performances.
[0137] The lubricating oil composition of the present invention
containing the above lubricating oil additive is usable as an
automatic transmission fluid or a continuously variable
transmission fluid and as a lubricating oil for construction or
agricultural machines equipped with a transmission having a wet
clutch or a wet brake, manual transmissions, motorcycle gasoline
engines, diesel engines, gas engines and shock absorbers.
* * * * *