U.S. patent application number 16/852377 was filed with the patent office on 2020-07-30 for ether compounds and related compositions.
The applicant listed for this patent is Castrol Limited. Invention is credited to John Philip DAVIES, Amit GOKHALE, Gordon LAMB, John REDSHAW, Peter SEDEN, Kevin WEST.
Application Number | 20200239801 16/852377 |
Document ID | 20200239801 / US20200239801 |
Family ID | 1000004765879 |
Filed Date | 2020-07-30 |
Patent Application | download [pdf] |
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United States Patent
Application |
20200239801 |
Kind Code |
A1 |
LAMB; Gordon ; et
al. |
July 30, 2020 |
ETHER COMPOUNDS AND RELATED COMPOSITIONS
Abstract
In some embodiments, a compound has the formula (I) where:
R.sub.1 and R.sub.2 are alkyl or, together with the carbon atom to
which they are attached, cycloalkyl; R.sub.3, R.sub.4 and R.sub.5
are H or alkyl (formula II); R.sub.6 is alkyl or where: R.sub.7 and
R.sub.8 are H, alkyl or, together with the carbon atom to which
they are attached, cycloalkyl; R.sub.9 is H or alkyl; X is alkylene
or is absent; and p is 0, 1, 2 or 3; and m and n are 0, 1, 2 or 3
provided that m is 0 when R.sub.4 and R.sub.5 are H. The compound
is suitable for use as a base stock which provides low volatility
for a given viscosity profile. The compound may be used in a
lubricant composition for an internal combustion engine.
##STR00001##
Inventors: |
LAMB; Gordon; (Naperville,
IL) ; GOKHALE; Amit; (Naperville, IL) ;
DAVIES; John Philip; (Naperville, IL) ; REDSHAW;
John; (Naperville, IL) ; SEDEN; Peter;
(Naperville, IL) ; WEST; Kevin; (Naperville,
IL) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Castrol Limited |
Reading |
|
GB |
|
|
Family ID: |
1000004765879 |
Appl. No.: |
16/852377 |
Filed: |
April 17, 2020 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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15579788 |
Dec 5, 2017 |
10669499 |
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PCT/IB2016/000943 |
Jun 17, 2016 |
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16852377 |
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62181536 |
Jun 18, 2015 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C10N 2030/02 20130101;
C10N 2030/54 20200501; C07C 43/046 20130101; C07C 43/04 20130101;
C10M 2203/1006 20130101; C10N 2030/04 20130101; C10M 105/18
20130101; C10N 2030/10 20130101; C10M 2207/0225 20130101; C10N
2020/065 20200501; C10N 2030/74 20200501; C10N 2020/02 20130101;
C10M 2207/0215 20130101; C10M 2203/1025 20130101; C10M 2205/0285
20130101; C10M 2207/0406 20130101; C10N 2040/25 20130101; C10N
2020/071 20200501 |
International
Class: |
C10M 105/18 20060101
C10M105/18; C07C 43/04 20060101 C07C043/04 |
Claims
1-33. (canceled)
34. A compound of formula (2): ##STR00068## where: R.sub.1 and
R.sub.2 are alkyl or, together with the carbon atom to which they
are attached, cycloalkyl; R.sub.3 and R.sub.5 are H or alkyl;
R.sub.4 is alkyl; R.sub.6 is alkyl; and n is 0, 1, 2 or 3, wherein
the compound contains a total number of carbon atoms of from 20 to
50.
35. The compound of claim 34, wherein the compound has the formula
(3): ##STR00069## where: R.sub.1 is alkyl; R.sub.3 and R.sub.5 are
H or alkyl; R.sub.4 is alkyl; R.sub.6 is alkyl; and n is 0, 1, 2 or
3.
36. The compound of claim 35, wherein the compound has the formula
(4): ##STR00070## where: R.sub.1 and R.sub.4 are C.sub.1-15 alkyl;
R.sub.3 and R.sub.5 are H or C.sub.1-15 alkyl.
37. The compound of claim 36, wherein: R.sub.1 is C.sub.4-12 alkyl;
R.sub.3 is H; R.sub.4 is C.sub.1-10 alkyl; and R.sub.5 is H.
38. The compound of claim 34, wherein the compound has the formula
(10): ##STR00071## where: R.sub.1 and R.sub.4 are alkyl; R.sub.3
and R.sub.5 are H or alkyl; R.sub.6 is alkyl.
39. The compound of claim 34, wherein R.sub.1 and R.sub.2 are
C.sub.1-15 alkyl or, together with the carbon atom to which they
are attached, C.sub.5-30 cycloalkyl; R.sub.3 and R.sub.5 are H or
C.sub.1-15 alkyl; R.sub.4 is C.sub.1-15 alkyl; R.sub.6 is
C.sub.1-15 alkyl; and n is 0, 1, or 2.
40. The compound of claim 34, wherein R.sub.1 and R.sub.2 are
C.sub.2-12 alkyl or, together with the carbon atom to which they
are attached, C.sub.5-25 cycloalkyl; R.sub.3 and R.sub.5 are H or
C.sub.2-12 alkyl; R.sub.4 is C.sub.2-12 alkyl; R.sub.6 is
C.sub.2-12 alkyl; and n is 0, 1, or 2.
41. The compound of claim 34, wherein R.sub.1 and R.sub.2 are
C.sub.2-12 alkyl or, together with the carbon atom to which they
are attached, C.sub.5-25 cycloalkyl; R.sub.3 is H or C.sub.2-12
alkyl; R.sub.4 is C.sub.2-12 alkyl; R.sub.5 is H; R.sub.6 is
C.sub.2-12 alkyl; and n is 0 or 1.
42. The compound of claim 36, wherein: R.sub.1 is C.sub.6-10 alkyl;
R.sub.3 is H; R.sub.4 is C.sub.2-8 alkyl; and R.sub.5 is H.
43. The compound of claim 34, wherein the compound is prepared from
bio-derived feedstock.
44. The compound of claim 34, wherein the compound contains greater
than 50% by weight of biobased carbon.
45. The compound of claim 34, wherein the compound has at least one
of: a kinematic viscosity at 40.degree. C. of less than 25 cSt; a
kinematic viscosity at 100.degree. C. of less than 7 cSt; a
viscosity index of greater than 100; a viscosity at 150.degree. C.
and a shear rate of 10.sup.6 s.sup.-1 of no greater than 1.7 cP; a
Noack volatility of less than 26% by weight; and a pour point of
less than -10.degree. C.
46. The compound of claim 34, wherein the compound has a kinematic
viscosity at 100.degree. C. of 3 to 4 cSt and a Noack volatility of
less than 20% by weight; or a kinematic viscosity at 100.degree. C.
of 2 to 3 cSt, and a Noack volatility of less than 40% by
weight.
47. A base oil comprising a compound as defined in claim 34.
48. The base oil of claim 47, wherein the base oil comprises
greater than 10% by weight of the compound.
49. The base oil of claim 47, wherein the base oil comprises a base
stock selected from Group I, Group II, Group III, Group IV and
Group V base stocks and mixtures thereof.
50. A lubricant composition comprising a base oil as defined in
claim 47.
51. The lubricant composition of claim 47, wherein the lubricant
composition comprises greater than 50% by weight of the base
oil.
52. The lubricant composition of claim 47, wherein the lubricant
composition has at least one of: a kinematic viscosity at
40.degree. C. of less than 60 cSt; a kinematic viscosity at
100.degree. C. of less than 12 cSt; a viscosity index of greater
than 100; a viscosity at 150.degree. C. and a shear rate of
10.sup.6 s.sup.-1 of no greater than 3 cP; and a Noack volatility
of less than 25% by weight.
53. A method of preparing a base oil, said method comprising
providing a compound as defined in claim 34, and preparing a base
oil comprising said compound.
54. A method of preparing a lubricant composition, said method
comprising providing a base oil as defined in claim 47, and
blending the base oil with one or more lubricant additives to
prepare the lubricant composition.
55. A method of improving the oxidative stability performance, fuel
economy performance, and/or piston cleanliness performance of a
lubricating composition, comprising the step of providing to the
lubricating composition a compound according to claim 34.
56. A method of improving the oxidative stability performance, fuel
economy performance, and/or piston cleanliness performance of a
lubricating composition, comprising the step of providing to the
lubricating composition a base oil according claim 47.
57. A method of lubricating a surface, said method comprising
supplying a lubricant composition as defined in claim 50 to said
surface.
Description
[0001] The present invention relates, in part, to compounds which
may be used as base stocks, in particular as base stocks which have
a low volatility for a given viscosity profile, and which are
suitable for use in a lubricant composition for an internal
combustion engine. Base oils comprising said compounds and
lubricant compositions comprising said base oils are also
provided.
BACKGROUND
[0002] Lubricating compositions generally comprise a base oil of
lubricating viscosity together with one or more additives to
deliver properties including for example, reduced friction and
wear, improved viscosity index, detergency, and resistance to
oxidation and corrosion. A lubricant base oil may comprise one or
more lubricating base stocks.
[0003] Lubricant base stocks used in automotive engine lubricants
are generally obtained from petrochemical sources, for example they
may be obtained as the higher boiling fractions isolated during the
refining of crude oil or as the products of chemical reactions of
feedstocks from petrochemical sources. Lubricant base stocks can
also be made from Fischer-Tropsch wax.
[0004] Lubricant base stocks may be classified as Group I, II, III,
IV and V base stocks according to API standard 1509, "ENGINE OIL
LICENSING AND CERTIFICATION SYSTEM", 17.sup.th Edition, Annex E
(October 2013 with Errata March 2015), as set out in Table 1.
TABLE-US-00001 TABLE 1 Saturated hydrocarbon Sulphur content (% by
Viscosity content weight) Index (% by weight) ASTM D2622, D4294,
ASTM Group ASTM D2007 D4927, D3120 or D1552 D2270 I <90 and/
>0.03 and .gtoreq.80 and or <120 II .gtoreq.90 and
.ltoreq.0.03 and .gtoreq.80 and <120 III .gtoreq.90 and
.ltoreq.0.03 and .gtoreq.120 IV Polyalphaolefins V all base stocks
not in Groups I, II, III or IV
[0005] Group I base stocks are typically manufactured by known
processes including, for example, solvent extraction and solvent
dewaxing, or solvent extraction and catalytic dewaxing. Group II
and Group III base stocks are typically manufactured by known
processes including, for example, catalytic hydrogenation and/or
catalytic hydrocracking, and catalytic hydroisomerisation. Group IV
base stocks include for example, hydrogenated oligomers of alpha
olefins.
[0006] A combination of properties is desirable in a base stock. In
some instances, for example in passenger car engine oils, it may be
desirable for a base stock to have a low viscosity profile, since
this leads to improved fuel economy. In particular, it is desirable
for base stocks to have a low kinematic viscosity as well as good
low-temperature viscosity characteristics, for example a low pour
point or low viscosity as measured using a mini-rotary viscometer
(MRV). However, the general trend is for an improvement in the
viscosity profile (i.e. a reduction in viscosity parameters) of a
base oil to be accompanied by an undesirable increase in
volatility.
[0007] Accordingly, there is a need in the art for a base stock
having a desirable viscosity profile, including good
low-temperature viscosity characteristics, but which also exhibits
low volatility.
[0008] Problems may also be encountered when a base stock is
incorporated into a lubricating composition and used in an engine.
For instance, poor miscibility of a base stock with lubricant
additives or other base stocks may lead to problems in the engine,
for instance with piston cleanliness. Negative interactions between
a base stock and oil seals that are found in engines may, in some
cases, lead to loss of lubricant through failure of the oil seals.
Base stocks may also undergo oxidative degradation at the high
temperatures encountered in an engine. Base stocks containing polar
groups such as ester or other groups may be particularly prone to
at least some of these problems.
[0009] Accordingly, there is a need for a base stock having low
volatility for a given viscosity profile, but which is also
suitable for use, for example, in a lubricating composition for an
internal combustion engine.
SUMMARY
[0010] A compound of formula (1) is provided:
##STR00002##
where: [0011] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon atom to which they are attached, cycloalkyl; [0012] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl;
[0012] ##STR00003## [0013] R.sub.6 is alkyl or [0014] where: [0015]
R.sub.7 and R.sub.8 are H, alkyl or, together with the carbon atom
to which they are attached, cycloalkyl; [0016] R.sub.9 is H or
alkyl; [0017] X is alkylene or is absent; and [0018] p is 0, 1, 2
or 3; and [0019] m and n are 0, 1, 2 or 3 provided that m is 0 when
R.sub.4 and R.sub.5 are H.
[0020] Compounds of formula (1) may be used as base stocks.
[0021] Also provided is a base oil comprising a compound of formula
(1), as well as a lubricant composition comprising said base
oil.
[0022] Also provided are methods of preparing base oils and
lubricant compositions.
[0023] Also provided is a method for lubricating a surface using a
lubricant composition, as well as the use of a lubricant
composition for lubricating a surface.
[0024] Also provided are methods and uses of improving the
oxidative stability performance, fuel economy performance and/or
piston cleanliness performance of a lubricating composition, and of
improving the fuel economy performance and/or piston cleanliness
performance of an engine and/or vehicle.
DETAILED DESCRIPTION
Ether Base Stocks
[0025] A compound of formula (1) is provided:
##STR00004##
where: [0026] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon atom to which they are attached, cycloalkyl; [0027] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl;
[0027] ##STR00005## [0028] R.sub.6 is alkyl or [0029] where: [0030]
R.sub.7 and R.sub.8 are H, alkyl or, together with the carbon atom
to which they are attached, cycloalkyl; [0031] R.sub.9 is H or
alkyl; [0032] X is alkylene or is absent; and [0033] p is 0, 1, 2
or 3; and [0034] m and n are 0, 1, 2 or 3 provided that m is 0 when
R.sub.4 and R.sub.5 are H.
[0035] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon atom to which they are attached, C.sub.5-25
cycloalkyl.
[0036] In some embodiments, R.sub.3, R.sub.4 and R.sub.5 are H or
C.sub.1-15 alkyl, such as H or C.sub.2-12 alkyl. Preferably,
R.sub.5 is H.
##STR00006##
[0037] In some embodiments, R.sub.6 is C.sub.1-20 alkyl or such as
C.sub.1-16 alkyl or
##STR00007##
[0038] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0039] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0040] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0041] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0042] In some embodiments, m and n are 0, 1 or 2, such as 0 or
1.
[0043] R.sub.1 and R.sub.2 are as described as alkyl or, together
with the carbon atom to which they are attached, cycloalkyl. It
will be understood that, where R.sub.1 and R.sub.2 are both alkyl
groups, they may be the same as or different from one another.
Similar considerations apply to other substituents which are
defined as part of a group of substituents. Thus, the
considerations apply, for example, to R.sub.3, R.sub.4 and R.sub.5;
to R.sub.7 and R.sub.8; and to the values taken by m and n. For
instance, where R.sub.3, R.sub.4 and R.sub.5 are described as being
H or alkyl, it will be understood that each of R.sub.3, R.sub.4 and
R.sub.5 may be H, each of R.sub.3, R.sub.4 and R.sub.5 may be
alkyl, or a subset of R.sub.3, R.sub.4 and R.sub.5 may be H and a
subset alkyl. Where R.sub.3, R.sub.4 and R.sub.5, or a subset
thereof, are alkyl, each of R.sub.3, R.sub.4 and R.sub.5 may be the
same alkyl group or they may be different alkyl groups. In
contrast, where R.sub.1 (or any other notation) is used at a number
of locations in a formula, it is used to denote the presence of the
same group at each of these locations.
[0044] In each of the embodiments disclosed herein, the compounds
may contain a total number of carbons atoms of from about 20 to
about 50. For instance, the total number of carbons in the
compounds may be from about 25 to about 45, such as from about 28
to about 40 or from about 30 to about 36.
[0045] The alkyl and alkylene groups mentioned herein, i.e. those
that may be represented by R.sub.1, R.sub.2, R.sub.3, R.sub.4,
R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9 and X, may be straight
chain alkyl or alkylene groups, though they may also be branched.
In some embodiments, each alkyl group and each alkylene group
contains a single branch point or is a straight chain alkyl or
alkylene group. The alkyl and alkylene groups are preferably
straight chain alkyl or alkylene groups. It will be understood
that, aside from alkyl branching (if present), the alkyl and
alkylene groups are unsubstituted and so they do not contain any
atoms other than carbon or hydrogen.
[0046] The cycloalkyl groups mentioned herein may contain a
cyclopentyl, cyclohexyl or cycloheptyl group optionally having
alkyl groups attached thereto.
[0047] The compounds of formula (1) may have a kinematic viscosity
at 40.degree. C. of less than about 25 cSt, such as less than about
20 cSt, or less than about 17 cSt. The compounds may have a
kinematic viscosity at 100.degree. C. of less than about 7 cSt,
such as less than about 5 cSt, or less than about 4 cSt. The
compounds may have a viscosity index of greater than about 100,
such as greater than about 110, or greater than about 120. The
kinematic viscosity at 40.degree. C. and the kinematic viscosity at
100.degree. C. may be measured according to ASTM D7279. The
viscosity index may be measured according to ASTM D2270.
[0048] The compounds may have a Noack volatility of less than about
26%, such as less than about 20%, less than about 16%, or less than
about 12% by weight. Noack volatility may be measured according to
CEC-L-40-A-93.
[0049] The compounds may have a viscosity at 150.degree. C. and a
shear rate of 10.sup.6 s.sup.-1 of no greater than 1.7 cP, such as
no greater than 1.5 cP. This high temperature high shear viscosity
may be measured according to CEC-L-36-A-90.
[0050] The compounds may be used to improve the oxidative
stability, fuel economy performance and/or piston cleanliness
performance of a lubricant composition, and/or the fuel economy
performance and/or piston cleanliness performance of an internal
combustion engine and/or a vehicle, such as an automotive vehicle
associated with an internal combustion engine. Accordingly, there
are provided methods of improving the fuel economy performance
and/or piston cleanliness performance of a lubricant composition an
internal combustion engine and/or a vehicle, such as an automotive
vehicle associated with an internal combustion engine, comprising
the step of providing or supplying to the lubricant composition,
engine and/or vehicle at least one of the compounds.
[0051] The compounds may have a pour point of less than -10.degree.
C., such as less than about -25.degree. C., or less than about
-35.degree. C. Pour point may be measured according to ASTM
D5950.
[0052] The compounds may have a cold-crankcase simulator viscosity
at -35.degree. C. of less than about 1800 cP, such as less than
about 1500 cP, or less than about 1200 cP, for example as measured
according to ASTM D5293.
[0053] The compounds may have a DSC oxidation onset temperature of
greater than about 165.degree. C., such as greater than about
175.degree. C., or greater than about 185.degree. C., for example
as measured according to ASTM E2009 (method B).
[0054] In particular embodiments, the compounds of formula (1) may
have a kinematic viscosity at 100.degree. C. of about 3 to about 4
cSt and a Noack volatility of less than about 20%, such as less
than about 16%, or less than about 12%, by weight; or a kinematic
viscosity at 100.degree. C. of about 2 to about 3 cSt, and a Noack
volatility of less than about 40%, such as less than about 30%, by
weight.
[0055] The compounds of formula (1) are also particularly suited
for blending into a lubricant composition. In particular, the
compounds are miscible with conventional base stocks, including
hydrocarbon base stocks, as well as with conventional lubricant
additives. Moreover, the compounds may be used in a lubricant
composition in a relatively high amount (for example, in an amount
of greater than about 10% by weight, such as greater than about 20%
by weight or greater than about 30% by weight) whilst meeting
elastomer compatibility requirements for lubricant
compositions.
[0056] The compounds of formula (1) may be prepared from a wide
range of commercially available feedstocks.
[0057] In some embodiments, the compounds are prepared from
bio-derived feedstocks. For instance, the compounds may contain
greater than about 50%, such as greater than about 70%, or greater
than about 90% by weight of biobased carbon. The biobased carbon
content of the compounds may be measured according to ASTM
D6866.
Guerbet-Derived Base Stocks
[0058] In preferred embodiments, the compounds of formula (1) are
derived from (3-alkylated alcohols. In these embodiments, the
compound may have the formula (2):
##STR00008##
where: [0059] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon atom to which they are attached, cycloalkyl; [0060] R.sub.3
and R.sub.5 are H or alkyl; [0061] R.sub.4 is alkyl;
[0061] ##STR00009## [0062] R.sub.6 is alkyl or [0063] where: [0064]
R.sub.7 and R.sub.8 are H, alkyl or, together with the carbon atom
to which they are attached, cycloalkyl; [0065] R.sub.9 is H or
alkyl; [0066] X is alkylene or is absent; and [0067] p is 0, 1, 2
or 3; and [0068] n is 0, 1, 2 or 3.
[0069] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon atom to which they are attached, C.sub.5-25 cycloalkyl.
Preferably, R.sub.1 and R.sub.2 are C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0070] In some embodiments, R.sub.3 and R.sub.5 are H or C.sub.1-15
alkyl, such as H or C.sub.2-12 alkyl. Preferably, R.sub.3 and
R.sub.5 are H.
[0071] In some embodiments, R.sub.4 is C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
##STR00010##
[0072] In some embodiments, R.sub.6 is C.sub.1-15 alkyl or such as
C.sub.1-12 alkyl or
##STR00011##
[0073] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0074] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0075] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0076] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0077] In some embodiments, n is 0, 1 or 2, such as 0 or 1.
[0078] Where the compound is derived from a .beta.-alkylated
alcohol, it is preferably derived, at least in part, from a Guerbet
alcohol. Compounds which are derived, at least in part, from
Guerbet alcohols may have the formula (3):
##STR00012##
where: [0079] R.sub.1 is alkyl; [0080] R.sub.3 and R.sub.5 are H or
alkyl; [0081] R.sub.4 is alkyl; [0082] R.sub.6 is alkyl or
[0082] ##STR00013## [0083] where: [0084] R.sub.7 and R.sub.8 are H,
alkyl or, together with the carbon atom to which they are attached,
cycloalkyl; [0085] R.sub.9 is H or alkyl; [0086] X is alkylene or
is absent; and [0087] p is 0, 1, 2 or 3; and [0088] n is 0, 1, 2 or
3.
[0089] In some embodiments, R.sub.1 is C.sub.1-12 alkyl, such as
C.sub.2-10 alkyl.
[0090] In some embodiments, R.sub.3 is H or C.sub.1-12 alkyl, such
as H or C.sub.2-10 alkyl. Preferably, R.sub.3 is H.
[0091] In some embodiments, R.sub.4 is C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0092] In some embodiments, R.sub.5 is H or C.sub.1-15 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.5 is H.
[0093] In some embodiments, R.sub.6 is C.sub.1-15 alkyl or
##STR00014##
such as C.sub.1-12 alkyl or
##STR00015##
Preferably, R.sub.6 is C.sub.1-15 alkyl, such as C.sub.1-12
alkyl.
[0094] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0095] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0096] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0097] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0098] In some embodiments, n is 0, 1 or 2, such as 0 or 1.
[0099] One portion of the compound of formula (3) has a structure
which may be derived from a Guerbet alcohol (i.e. the portion
containing R.sub.1 and R.sub.3), whereas the other portion need not
be derived from a Guerbet alcohol (i.e. the portion containing
R.sub.4, R.sub.5 and R.sub.6). However, in preferred embodiments,
the compound may be derived from a combination of two Guerbet
alcohols. A compound prepared in this way may have the formula
(4):
##STR00016##
where: [0100] R.sub.1 and R.sub.4 are alkyl; [0101] R.sub.3 and
R.sub.5 are H or alkyl.
[0102] In some embodiments, R.sub.1 and R.sub.4 are C.sub.1-12
alkyl, such as C.sub.2-10 alkyl.
[0103] In some embodiments, R.sub.3 and R.sub.5 are H or C.sub.1-12
alkyl, such as H or C.sub.2-10 alkyl. Preferably, R.sub.3 and
R.sub.5 are H.
[0104] In particular embodiments: [0105] R.sub.1 is C.sub.4-12
alkyl, such as C.sub.6-10 alkyl; [0106] R.sub.3 is H; [0107]
R.sub.4 is C.sub.1-10 alkyl, such as C.sub.2-8 alkyl; and [0108]
R.sub.5 is H.
[0109] Two different Guerbet alcohols may be combined to form
compounds of formula (4), in which case R.sub.1 and R.sub.4 may be
different. Alternatively, R.sub.3 and R.sub.5 may be different. In
some embodiments, R.sub.1 and R.sub.4 are different and R.sub.3 and
R.sub.5 are also different.
[0110] However, in some embodiments, the compound may be derived
from a reaction in which the same Guerbet alcohols are combined. A
compound prepared in this way may have the formula (5):
##STR00017##
where: [0111] R.sub.1 is alkyl; and [0112] R.sub.3 is H or
alkyl.
[0113] In some embodiments, R.sub.1 is C.sub.1-10 alkyl, such as
C.sub.2-9 alkyl.
[0114] In some embodiments, R.sub.3 is H or C.sub.1-9 alkyl, such
as H or C.sub.2-8 alkyl. Preferably, R.sub.3 is H.
[0115] In particular embodiments: [0116] R.sub.1 is C.sub.3-10
alkyl, such as C.sub.4-8 alkyl; and [0117] R.sub.3 is H.
[0118] Compounds that are derived from Guerbet alcohols include
compounds GE1-GE3, GE5, GE7-GE9, SE1, SE2 and TE1 as shown in Table
3.
[0119] Guerbet alcohols may be prepared, for example, by dimerising
primary alcohols to form a .beta.-alkylated alcohol product in a
Guerbet reaction:
##STR00018##
where R.sub.1 and R.sub.3 are as defined previously; and/or:
##STR00019##
where R.sub.4 and R.sub.5 are as defined previously.
[0120] Guerbet reactions are well-known to the skilled person. The
reactions are typically carried out at elevated temperatures in the
presence of a catalyst.
[0121] The compound may be prepared from the Guerbet alcohol, for
example, according to the following reaction:
##STR00020##
where: [0122] Y is a leaving group; and [0123] R.sub.1, R.sub.3,
R.sub.4, R.sub.5, R.sub.6 and n are as defined previously for the
compound of formula (3).
[0124] Where two Guerbet alcohols are combined to form a compound,
one of the Guerbet alcohols may first be modified so that it
contains a leaving group, Y, and the compound then prepared:
##STR00021##
then:
##STR00022##
or:
##STR00023##
then:
##STR00024##
where: [0125] Y is a leaving group; and [0126] R.sub.1, R.sub.3,
R.sub.4 and R.sub.5 are as defined previously for the compound of
formula (4).
[0127] Where the same Guerbet alcohols are combined to form a
compound, they may be combined, for example, according to the
following reactions:
##STR00025##
then:
##STR00026##
where: [0128] Y is a leaving group; and [0129] R.sub.1 and R.sub.3
are as defined previously for the compound of formula (5).
[0130] Methods and reaction conditions for modifying a Guerbet
alcohol so that it contains a leaving group, Y, are known to the
skilled person. For instance, a mesylate group may be introduced by
reacting the Guerbet alcohol with mesyl chloride in the presence of
triethylamine. A bromide group may be introduced by reacting the
Guerbet alcohol with N-bromosuccinimide and triphenyl
phosphine.
[0131] Methods and reaction conditions for carrying out
etherification reactions are known to the skilled person. A base
(for example potassium hydroxide or potassium tert-butoxide), a
catalyst (for example Starks' catalyst:
N-Methyl-N,N,N-trioctyloctan-1-ammonium chloride) or both may be
used in the abovementioned compound forming reactions, i.e. the
etherification reactions.
[0132] In the abovementioned compound forming reactions, Y may be
any suitable leaving group, such as a halogen (for example bromine,
chlorine or iodine) or a sulfonate ester (for example mesylate or
tosylate).
Secondary and Tertiary Ether Base Stocks
[0133] In some preferred embodiments, the compounds of formula (1)
are secondary or tertiary ether compounds. In these embodiments,
the compound may have the formula (6):
##STR00027##
where: [0134] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon to which they are attached, cycloalkyl; [0135] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl; [0136] R.sub.6 is alkyl or
[0136] ##STR00028## [0137] where: [0138] R.sub.7 and R.sub.8 are H,
alkyl or, together with the carbon atom to which they are attached,
cycloalkyl; [0139] R.sub.9 is H or alkyl; [0140] X is alkylene or
is absent; and [0141] p is 0, 1, 2 or 3; and [0142] n is 0, 1, 2 or
3.
[0143] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon atom to which they are attached, C.sub.5-25 cycloalkyl.
Preferably, R.sub.1 and R.sub.2 are C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0144] In some embodiments, R.sub.3, R.sub.4 and R.sub.5 are H or
C.sub.1-15 alkyl, such as H or C.sub.2-12 alkyl. Preferably,
R.sub.5 is H.
[0145] In some embodiments, R.sub.6 is C.sub.1-20 alkyl or
##STR00029##
such as C.sub.1-16 alkyl or
##STR00030##
[0146] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0147] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0148] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0149] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0150] In some embodiments, n is 0, 1 or 2, such as 0 or 1.
[0151] Secondary and tertiary ether compounds may have the formula
(7):
##STR00031##
where: [0152] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon to which they are attached, cycloalkyl; [0153] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl; and [0154] R.sub.6 is
alkyl.
[0155] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon to which they are attached, C.sub.5-25 cycloalkyl.
[0156] In some embodiments, R.sub.3, R.sub.4 and R.sub.5 are H or
C.sub.1-15 alkyl, such as H or C.sub.2-12 alkyl. Preferably,
R.sub.5 is H.
[0157] In some embodiments, R.sub.6 is C.sub.1-20 alkyl, such as
C.sub.1-16 alkyl.
[0158] The compounds may be secondary ether compounds of formula
(8):
##STR00032##
where: [0159] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon to which they are attached, cycloalkyl; [0160] R.sub.4 and
R.sub.5 are H or alkyl; and [0161] R.sub.6 is alkyl.
[0162] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl, such as C.sub.2-12 alkyl.
[0163] In other embodiments, the secondary ether may be obtained
from a cyclic compound. In this case, R.sub.1 and R.sub.2, together
with the carbon to which they are attached, form a cycloalkyl
group, such as a C.sub.5-30 cycloalkyl or a C.sub.5-25 cycloalkyl.
The cycloalkyl group may contain a cyclopentyl, cyclohexyl or
cycloheptyl group optionally having one or more alkyl groups, such
as C.sub.1-12 alkyl or C.sub.1-8 alkyl, attached thereto.
[0164] In some embodiments, R.sub.4 and R.sub.5 are H or C.sub.1-15
alkyl, such as H or C.sub.2-12 alkyl. Preferably, R.sub.5 is H.
[0165] In some embodiments, R.sub.6 is C.sub.1-20 alkyl, such as
C.sub.1-16 alkyl.
[0166] In particular embodiments: [0167] R.sub.1 and R.sub.2 are
C.sub.3-12 alkyl, such as C.sub.5-10 alkyl; [0168] R.sub.4 and
R.sub.5 are H; and [0169] R.sub.6 is C.sub.4-20 alkyl, such as
C.sub.6-15 alkyl.
[0170] In other particular embodiments: [0171] R.sub.1 and R.sub.2
are C.sub.3-12 alkyl, such as C.sub.5-10 alkyl; [0172] R.sub.4 is
C.sub.3-12 alkyl, such as C.sub.5-10 alkyl; [0173] R.sub.5 is H;
and [0174] R.sub.6 is C.sub.3-12 alkyl, such as C.sub.5-10
alkyl.
[0175] The compounds may be tertiary ether compounds of formula
(9):
##STR00033##
where: [0176] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon to which they are attached, cycloalkyl; [0177] R.sub.3 is
alkyl; [0178] R.sub.4 and R.sub.5 are H or alkyl; and [0179]
R.sub.6 is alkyl.
[0180] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon to which they are attached, C.sub.5-25 cycloalkyl.
Preferably, R.sub.1 and R.sub.2 are C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0181] In some embodiments, R.sub.3 is C.sub.1-12 alkyl, such as
C.sub.1-10 alkyl.
[0182] In some embodiments, R.sub.4 and R.sub.5 are H or C.sub.1-15
alkyl, such as H or C.sub.2-12 alkyl.
[0183] In some embodiments, R.sub.6 is C.sub.1-20 alkyl, such as
C.sub.1-16 alkyl.
[0184] In particular embodiments: [0185] R.sub.1 and R.sub.2 are
C.sub.2-12 alkyl, such as C.sub.4-10 alkyl; [0186] R.sub.3 is
C.sub.1-10 alkyl, such as C.sub.1-8 alkyl; [0187] R.sub.4 and
R.sub.5 are H; and [0188] R.sub.6 is C.sub.4-20 alkyl, such as
C.sub.6-15 alkyl.
[0189] In other particular embodiments: [0190] R.sub.1, R.sub.2 and
R.sub.3 are C.sub.2-12 alkyl, such as C.sub.4-10 alkyl; [0191]
R.sub.3 is C.sub.1-10 alkyl, such as C.sub.1-8 alkyl; [0192]
R.sub.4 is C.sub.3-12 alkyl, such as C.sub.5-10 alkyl; [0193]
R.sub.5 is H; and [0194] R.sub.6 is C.sub.3-12 alkyl, such as
C.sub.5-10 alkyl.
[0195] Examples of secondary and tertiary ether compounds include
SE1, SE2 and TE1 as shown in Table 3.
[0196] The secondary and tertiary ether compounds may be prepared
according to the following reactions:
##STR00034##
or:
##STR00035##
where: [0197] Y is a leaving group; and [0198] R.sub.1, R.sub.2,
R.sub.3, R.sub.4, R.sub.5, R.sub.6 and n are as defined previously
for the compound of formula (6).
[0199] Similarly:
##STR00036##
or:
##STR00037##
where: Y is a leaving group; and [0200] R.sub.1, R.sub.2, R.sub.3,
R.sub.4, R.sub.5 and R.sub.6 are as defined previously for the
compound of formula (7).
[0201] The skilled person will be aware of methods and reaction
conditions for carrying out these etherification reactions. For
instance, the reaction may be carried out in the presence of
magnesium sulfate, sulfuric acid and dichloromethane.
[0202] Secondary and tertiary alcohol starting materials for use in
etherification reactions will generally be commercially available,
or they may be obtained from commercially available ketones.
[0203] The groups
##STR00038##
may be prepared by introducing a leaving group, Y, into the alcohol
starting materials. Methods and reaction conditions for introducing
the leaving group into alcohol are known to the skilled person.
[0204] In the abovementioned secondary and tertiary ether compound
forming reactions, Y may be any suitable leaving group, such as a
halogen (for example bromine, chlorine or iodine) or a sulfonate
ester (for example mesylate or tosylate).
Secondary or Tertiary Ethers Derived from a Guerbet Alcohol
[0205] In some embodiments, the compound may comprise an ether
which is derived on one side from a secondary or tertiary alcohol
and is derived on the other side from a Guerbet alcohol. In these
embodiments, the compound may have the formula (10):
##STR00039##
where: [0206] R.sub.1 and R.sub.4 are alkyl; [0207] R.sub.3 and
R.sub.5 are H or alkyl; [0208] R.sub.6 is alkyl or
[0208] ##STR00040## [0209] where: [0210] R.sub.7 and R.sub.8 are H,
alkyl or, together with the carbon atom to which they are attached,
cycloalkyl; [0211] R.sub.9 is H or alkyl; [0212] X is alkylene or
is absent; and [0213] and p is 0, 1, 2 or 3.
[0214] In some embodiments, R.sub.1 is C.sub.1-12 alkyl, such as
C.sub.2-10 alkyl.
[0215] In some embodiments, R.sub.3 is H or C.sub.1-12 alkyl, such
as H or C.sub.2-10 alkyl. Preferably, R.sub.3 is H.
[0216] In some embodiments, R.sub.4 is C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0217] In some embodiments, R.sub.5 is H or C.sub.1-15 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.5 is H.
##STR00041##
[0218] In some embodiments, R.sub.6 is C.sub.1-15 alkyl or such as
C.sub.1-12 alkyl or
##STR00042##
[0219] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0220] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0221] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0222] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0223] Examples of secondary and tertiary ether compounds derived
from a Guerbet-alcohol include compounds SE1, SE2 and TE1 as shown
in Table 3.
Di-Ether Base Stocks
[0224] It is generally preferred that the compounds of formula (1)
are monoethers. However, in some embodiments, the compound is a
diether compound. Such compounds may have the formula (11):
##STR00043##
where: [0225] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon atom to which they are attached, cycloalkyl; [0226] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl; [0227] R.sub.7 and R.sub.8 are
H, alkyl or, together with the carbon atom to which they are
attached, cycloalkyl; [0228] R.sub.9 is H or alkyl; [0229] X is
alkylene or is absent; [0230] p is 0, 1, 2 or 3; and [0231] m and n
are 0, 1, 2 or 3.
[0232] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon to which they are attached, C.sub.5-25 cycloalkyl.
Preferably, R.sub.1 and R.sub.2 are C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0233] In some embodiments, R.sub.3, R.sub.4 and R.sub.5 are H or
C.sub.1-15 alkyl, such as H or C.sub.2-12 alkyl. Preferably,
R.sub.3 and R.sub.5 are H.
[0234] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0235] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0236] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0237] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0238] In some embodiments, m and n are 0, 1 or 2, such as 0 or
1.
[0239] In some embodiments, the diether compound may contain two
ether groups, at least one of which is derived from a
.beta.-alkylated alcohol. In such embodiments, the compound may
have the formula (12):
##STR00044##
where: [0240] R.sub.1 and R.sub.2 are alkyl or, together with the
carbon atom to which they are attached, cycloalkyl; [0241] R.sub.3,
R.sub.4 and R.sub.5 are H or alkyl; [0242] R.sub.7 and R.sub.8 are
H, alkyl or, together with the carbon atom to which they are
attached, cycloalkyl; [0243] R.sub.9 is H or alkyl; [0244] X is
alkylene or is absent; [0245] p is 0, 1, 2 or 3; and [0246] n is 0,
1, 2 or 3.
[0247] In some embodiments, R.sub.1 and R.sub.2 are C.sub.1-15
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as C.sub.2-12 alkyl or, together with
the carbon atom to which they are attached, C.sub.5-25 cycloalkyl.
Preferably, R.sub.1 and R.sub.2 are C.sub.1-15 alkyl, such as
C.sub.2-12 alkyl.
[0248] In some embodiments, R.sub.3, R.sub.4 and R.sub.5 are H or
C.sub.1-15 alkyl, such as H or C.sub.2-12 alkyl. Preferably,
R.sub.3 and R.sub.5 are H. Preferably, R.sub.4 is C.sub.1-15 alkyl,
such as C.sub.2-12 alkyl
[0249] In some embodiments, R.sub.7 and R.sub.8 are H, C.sub.1-20
alkyl or, together with the carbon atom to which they are attached,
C.sub.5-30 cycloalkyl, such as H, C.sub.2-12 alkyl or, together
with the carbon atom to which they are attached, C.sub.5-25
cycloalkyl. Preferably, R.sub.7 and R.sub.8 are C.sub.1-20 alkyl,
such as C.sub.2-12 alkyl.
[0250] In some embodiments, R.sub.9 is H or C.sub.1-20 alkyl, such
as H or C.sub.2-12 alkyl. Preferably, R.sub.9 is H.
[0251] In some embodiments, X is C.sub.1-20 alkylene, such as
C.sub.3-15 alkylene.
[0252] In some embodiments, p is 0, 1 or 2, such as 0 or 1.
[0253] In some embodiments, n is 0, 1 or 2, such as 0 or 1.
Base Oils and Lubricant Compositions
[0254] The compounds of formula (1) may be used as part of a base
oil.
[0255] The base oils may contain an amount of compound of formula
(1) which is sufficient to impart beneficial properties of the
compound onto the base oil.
[0256] In some embodiments, the base oil comprises greater than
about 5%, such as greater than about 25%, or greater than about 40%
by weight of compound of formula (1). The base oil may comprise up
to about 100%, such as up to about 90% of compound of formula (1).
The compound of formula (1) in the base oil may be composed of a
single compound or a combination of compounds of formula (1).
[0257] The remainder of the base oil may be made up with base
stocks which are not compounds of formula (1). Base stocks other
than those of formula (1) which are suitable for use in the base
oil include non-aqueous base stocks, such as Group I, Group II,
Group III, Group IV and Group V base stocks. The remainder of the
base oil may comprise a single base stock or a combination of base
stocks other than those of formula (1).
[0258] The base oils may be used as part of a lubricant
composition.
[0259] The lubricant compositions may contain an amount of base oil
which is sufficient to impart beneficial properties of the compound
of formula (1) onto the lubricating composition.
[0260] In some embodiments, the lubricant composition comprises
greater than about 50%, such as greater than about 65%, or greater
than about 80% by weight of base oil. The base oil may be composed
of a single base oil or a combination of base oils comprising
compound of formula (1).
[0261] The lubricant composition may also comprise lubricant
additives. The lubricant composition may comprise a single
lubricant additive, though it will typically comprise a combination
of lubricant additives. The lubricant additives will typically be
present in the lubricant composition in an amount of from about 5%
to about 40% by weight, such as about 10% to about 30% by
weight.
[0262] Suitable lubricant additives include detergents (including
metallic and non-metallic detergents), friction modifiers,
dispersants (including metallic and non-metallic dispersants),
viscosity modifiers, dispersant viscosity modifiers, viscosity
index improvers, pour point depressants, anti-wear additives, rust
inhibitors, corrosion inhibitors, antioxidants (sometimes also
called oxidation inhibitors), anti-foams (sometimes also called
anti-foaming agents), seal swell agents (sometimes also called seal
compatibility agents), extreme pressure additives (including
metallic, non-metallic, phosphorus containing, non-phosphorus
containing, sulphur containing and non-sulphur containing extreme
pressure additives), surfactants, demulsifiers, anti-seizure
agents, wax modifiers, lubricity agents, anti-staining agents,
chromophoric agents, metal deactivators, and mixtures of two or
more thereof.
[0263] In some embodiments, the lubricant composition comprises a
detergent. Examples of detergents include ashless detergents (that
is, non-metal containing detergents) and metal-containing
detergents. Suitable non-metallic detergents are described for
example in U.S. Pat. No. 7,622,431. Metal-containing detergents
comprise at least one metal salt of at least one organic acid,
which is called soap or surfactant. Suitable organic acids include
for example, sulphonic acids, phenols (suitably sulphurised and
including for example, phenols with more than one hydroxyl group,
phenols with fused aromatic rings, phenols which have been modified
for example, alkylene bridged phenols, and Mannich base-condensed
phenols and saligenin-type phenols, produced for example by
reaction of phenol and an aldehyde under basic conditions) and
sulphurised derivatives thereof, and carboxylic acids including for
example, aromatic carboxylic acids (for example
hydrocarbyl-substituted salicylic acids and derivatives thereof,
for example hydrocarbyl substituted salicylic acids and sulphurised
derivatives thereof).
[0264] In some embodiments, the lubricant composition comprises a
friction modifier. Suitable friction modifiers include for example,
ash-producing additives and ashless additives. Examples of suitable
friction modifiers include fatty acid derivatives including for
example, fatty acid esters, amides, amines, and ethoxylated amines.
Examples of suitable ester friction modifiers include esters of
glycerol for example, mono-, di-, and tri-oleates, mono-palmitates
and mono-myristates. A particularly suitable fatty acid ester
friction modifier is glycerol monooleate. Examples of suitable
friction modifiers also include molybdenum compounds for example,
organo molybdenum compounds, molybdenum dialkyldithiocarbamates,
molybdenum dialkylthiophosphates, molybdenum disulphide,
tri-molybdenum cluster dialkyldithiocarbamates, non-sulphur
molybdenum compounds and the like. Suitable molybdenum-containing
compounds are described for example, in EP 1533362 A1 for example
in paragraphs [0101] to [0117].
[0265] In some embodiments, the lubricant composition comprises a
dispersant. Examples of suitable ashless dispersants include oil
soluble salts, esters, amino-esters, amides, imides and oxazolines
of long chain hydrocarbon-substituted mono- and polycarboxylic
acids or anhydrides thereof; thiocarboxylate derivatives of long
chain hydrocarbons; long chain aliphatic hydrocarbons containing
polyamine moieties attached directly thereto; Mannich condensation
products formed by condensing a long chain substituted phenol with
formaldehyde and polyalkylene polyamine; Koch reaction products and
the like.
[0266] In some embodiments, the lubricant composition comprises a
dispersant viscosity modifier. Examples of suitable dispersant
viscosity modifiers and methods of making them are described in WO
99/21902, WO 2003/099890 and WO 2006/099250.
[0267] In some embodiments, the lubricant composition comprises a
viscosity index improver. Examples of suitable viscosity modifiers
include high molecular weight hydrocarbon polymers (for example
polyisobutylene, copolymers of ethylene and propylene and higher
alpha-olefins); polyesters (for example polymethacrylates);
hydrogenated poly(styrene-co-butadiene or isoprene) polymers and
modifications (for example star polymers); and esterified
poly(styrene-co-maleic anhydride) polymers. Oil-soluble viscosity
modifying polymers generally exhibit number average molecular
weights of at least about 15000 to about 1000000, such as about
20000 to about 600000 as determined by gel permeation
chromatography or light scattering methods.
[0268] In some embodiments, the lubricant composition comprises a
pour point depressant. Examples of suitable pour point depressants
include C.sub.8 to C.sub.18 dialkyl fumarate/vinyl acetate
copolymers, methacrylates, polyacrylates, polyarylamides,
polymethacrylates, polyalkyl methacrylates, vinyl fumarates,
styrene esters, condensation products of haloparaffin waxes and
aromatic compounds, vinyl carboxylate polymers, terpolymers of
dialkyfumarates, vinyl esters of fatty acids and allyl vinyl
ethers, wax naphthalene and the like. In at least some examples,
the at least one lubricant additive includes at least one anti-wear
additive. Examples of suitable anti-wear additives include
non-phosphorus containing additives for example, sulphurised
olefins. Examples of suitable anti-wear additives also include
phosphorus-containing anti-wear additives. Examples of suitable
ashless phosphorus-containing anti-wear additives include trilauryl
phosphite and triphenylphosphorothionate and those disclosed in
paragraph [0036] of US 2005/0198894. Examples of suitable
ash-forming, phosphorus-containing anti-wear additives include
dihydrocarbyl dithiophosphate metal salts. Examples of suitable
metals of the dihydrocarbyl dithiophosphate metal salts include
alkali and alkaline earth metals, aluminium, lead, tin, molybdenum,
manganese, nickel, copper and zinc. Particularly suitable
dihydrocarbyl dithiophosphate metal salts are zinc dihydrocarbyl
dithiophosphates (ZDDP).
[0269] In some embodiments, the lubricant composition comprises a
rust inhibitor. Examples of suitable rust inhibitors include
non-ionic polyoxyalkylene polyols and esters thereof,
polyoxyalkylene phenols, polyoxyalkylene polyols, anionic alky
sulphonic acids, zinc dithiophosphates, metal phenolates, basic
metal sulphonates, fatty acids and amines.
[0270] In some embodiments, the lubricant composition comprises a
corrosion inhibitor. Examples of suitable corrosion inhibitors
include phosphosulphurised hydrocarbons and the products obtained
by the reaction of phosphosulphurised hydrocarbon with an alkaline
earth metal oxide or hydroxide, non-ionic polyoxyalkylene polyols
and esters thereof, polyoxyalkylene phenols, thiadiazoles,
triazoles and anionic alkyl sulphonic acids. Examples of suitable
epoxidised ester corrosion inhibitors are described in US
2006/0090393.
[0271] In some embodiments, the lubricant composition comprises an
antioxidant. Examples of suitable antioxidants include alkylated
diphenylamines, N-alkylated phenylenediamines,
phenyl-a-naphthylamine, alkylated phenyl-a-naphthylamines,
dimethylquinolines, trimethyldihydroquinolines and oligomeric
compositions derived therefrom, hindered phenolics (including
ashless (metal-free) phenolic compounds and neutral and basic metal
salts of certain phenolic compounds), aromatic amines (including
alkylated and non-alkylated aromatic amines), sulphurised alkyl
phenols and alkali and alkaline earth metal salts thereof,
alkylated hydroquinones, hydroxylated thiodiphenyl ethers,
alkylidenebisphenols, thiopropionates, metallic dithiocarbamates,
1,3,4-dimercaptothiadiazole and derivatives, oil soluble copper
compounds (for example, copper dihydrocarbyl thio- or
thio-phosphate, copper salts of a synthetic or natural carboxylic
acids, for example a C.sub.8 to C.sub.18 fatty acid, an unsaturated
acid or a branched carboxylic acid, for example basic, neutral or
acidic Cu(I) and/or Cu(II) salts derived from alkenyl succinic
acids or anhydrides), alkaline earth metal salts of
alkylphenolthioesters, suitably containing C.sub.5 to C.sub.12
alkyl side chains, calcium nonylphenol sulphide, barium
t-octylphenyl sulphide, dioctylphenylamine, phosphosulphised or
sulphurised hydrocarbons, oil soluble phenates, oil soluble
sulphurised phenates, calcium dodecylphenol sulphide,
phosphosulphurised hydrocarbons, sulphurised hydrocarbons,
phosphorus esters, low sulphur peroxide decomposers and the
like.
[0272] In some embodiments, the lubricant composition comprises an
antifoam agent. Examples of suitable anti-foam agents include
silicones, organic polymers, siloxanes (including poly siloxanes
and (poly) dimethyl siloxanes, phenyl methyl siloxanes), acrylates
and the like.
[0273] In some embodiments, the lubricant composition comprises a
seal swell agent. Examples of suitable seal swell agents include
long chain organic acids, organic phosphates, aromatic esters,
aromatic hydrocarbons, esters (for example butylbenzyl phthalate)
and polybutenyl succinic anhydride.
[0274] The lubricant composition may comprise lubricant additives
in the amounts shown in Table 2.
TABLE-US-00002 TABLE 2 Lubricant composition Suitable amount
(actives) if present Preferred amount (actives) if present Additive
type by weight by weight Phosphorus-containing Corresponding to
about 10 to Corresponding to about 10 to anti-wear additives about
6000 ppm P about 1000 ppm P Molybdenum-containing Corresponding to
about 10 to Corresponding to about 40 to anti-wear additives about
1000 ppm Mo about 600 ppm Mo Boron-containing anti- Corresponding
to about 10 to Corresponding to about 50 to wear additives about
500 ppm B about 100 ppm B Friction modifiers About 0.01 to about 5%
About 0.01 to about 1.5% Molybdenum-containing Corresponding to
about 10 to Corresponding to about 400 friction modifiers about
1000 ppm Mo to about 600 ppm Mo Dispersants About 0.1 to about 20%
About 0.1 to about 8% Detergents About 0.01 to about 6% About 0.01
to about 4% Viscosity index improvers About 0.01 to about 20% About
0.01 to about 15% Pour point depressants About 0.01 to about 5%
About 0.01 to about 1.5% Corrosion and/or rust About 0.01 to about
5% About 0.01 to about 1.5% inhibitors Anti-oxidants About 0.01 to
about 10% About 0.5 to 5 about % Antifoams containing Corresponding
to about 1 to Corresponding to about 1 to silicon about 20 ppm Si
about 10 ppm Si
[0275] The lubricant compositions may have a kinematic viscosity at
40.degree. C. of less than about 60 cSt, such as less than about 55
cSt, or less than about 50 cSt. The lubricant compositions may have
a kinematic viscosity at 100.degree. C. of less than about 12 cSt,
such as less than about 10 cSt, or less than about 9.5 cSt. The
lubricant compositions may have a viscosity index of greater than
about 100, such as greater than about 110, or greater than about
120. The kinematic viscosity at 40.degree. C. and the kinematic
viscosity at 100.degree. C. may be measured according to ASTM D445.
The viscosity index may be calculated according to ASTM D2270.
[0276] The lubricant compositions may have a Noack volatility of
less than about 25%, such as less than about 15%, or less than
about 10% by weight. Noack volatility may be measured according to
CEC-L-40-A-93.
[0277] The lubricant compositions may have a viscosity at
150.degree. C. and a shear rate of 10.sup.6 s.sup.-1 of no greater
than 3 cP, such as no greater than 2.8 cP. This high temperature
high shear viscosity may be measured according to
CEC-L-36-A-90.
[0278] The lubricant composition may have at least one of:
[0279] an oxidative stability performance on a CEC-L-088-02 test
indicated by an absolute viscosity increase at 40.degree. C. of no
more than 45 cSt, such as no more than 35 cSt or no more than 25
cSt; a fuel economy performance on a CEC-L-054-96 test of at least
2.5%, such as at least 3%; and a piston cleanliness performance on
a CEC-L-088-02 test indicated by an overall piston merit of at
least 8.5, such as 9.
[0280] The lubricant compositions may have a cold-crankcase
simulator performance at -30.degree. C. of less than about 3000,
such as less than about 2800, or less than about 2750, for example
as measured according to ASTM D5293.
[0281] Preferred lubricant compositions meet the requirements set
out in SAE J300.
[0282] The lubricant compositions may be used in a method of
lubricating a surface.
[0283] Suitable surfaces include those in power transmission
systems for example drive lines and gear boxes for example for
vehicles including for example passenger vehicles and heavy duty
vehicles; and those in internal combustion engines, for example the
crankcases of internal combustion engines. Suitable surfaces also
include those in turbine bearings for example in water turbine
bearings.
[0284] Suitable internal combustion engines include, for example,
engines used in automotive applications, engines used in marine
applications and engines used in land-based power generation
plants. The lubricant compositions are particularly suited to use
in an automotive internal combustion engine.
[0285] The lubricant compositions may be used to improve the fuel
economy and/or piston cleanliness performance of an internal
combustion engine and/or a vehicle, such as an automotive vehicle
associated with an internal combustion engine. Accordingly, there
are provided methods of improving the fuel economy and/or piston
cleanliness performance of an internal combustion engine and/or a
vehicle, such as an automotive vehicle associated with an internal
combustion engine, comprising the step of providing or supplying to
the engine and/or vehicle at least one of the lubricant
compositions.
[0286] The invention will now be described with reference to the
accompanying figures and examples, which are not limiting in
nature, in which:
[0287] FIG. 1 is a graph of volatility against pour point for
compounds of formula (1), other ether base stocks and conventional
base stocks;
[0288] FIG. 2 is a graph of volatility against kinematic viscosity
at 100.degree. C. for compounds of formula (1), other ether base
stocks and conventional base stocks;
[0289] FIG. 3 is a graph of volatility against cold-cranking
simulator performance for compounds of formula (1) and conventional
base stocks;
[0290] FIG. 4a is a graph of kinematic viscosity at 40.degree. C.
against time of lubricant compositions containing compounds of
formula (1), a conventional hydrocarbon base stock and a
farnesene-derived ether base stock during a TU-5 JP engine
test;
[0291] FIG. 4b is a graph of absolute change in kinematic viscosity
at 40.degree. C. of lubricant compositions containing compounds of
formula (1), a conventional hydrocarbon base stock and a
farnesene-derived ether base stock during a TU-5 JP engine test;
and
[0292] FIG. 5 is a graph of overall piston merit performance of
lubricant compositions containing compounds of formula (1) and a
conventional hydrocarbon base stock during a TU-5 JP engine
test.
EXAMPLES
Example 1--Properties of Ether Base Stocks
[0293] Guerbet-derived base stocks GE1-GE3, GE5 and GE7-GE9,
secondary ether base stocks SE1 and SE2, and tertiary ether base
stock TE1 of formula (1) were prepared. Two further Guerbet-derived
base stocks, GE4 and GE6, and an experimental group V base stock of
the type previously described in WO 2014/207235, i.e. a
farnesene-derived ether base stock, were also prepared. The
structure of these compounds is shown in Table 3.
TABLE-US-00003 TABLE 3 Molec- ular Chemical Weight Formula
Structure GE1 466.87 C.sub.32H.sub.66O ##STR00045## GE2 466.87
C.sub.32H.sub.66O ##STR00046## GE3 522.97 C.sub.36H.sub.74O
##STR00047## GE4 466.87 C.sub.32H.sub.66O ##STR00048## GE5 410.76
C.sub.28H.sub.58O ##STR00049## GE6 466.87 C.sub.32H.sub.66O
##STR00050## GE7 522.57 C.sub.36H.sub.74O ##STR00051## GE8 382.42
C.sub.26H.sub.54O ##STR00052## GE9 466.51 C.sub.32H.sub.66O
##STR00053## GE10 410.76 C.sub.28H.sub.58O ##STR00054## GE12 382.71
C.sub.26H.sub.54O ##STR00055## GE14 410.76 C.sub.28H.sub.58O
##STR00056## GE15 354.65 C.sub.24H.sub.50O ##STR00057## GE16 424.79
C.sub.29H.sub.60O ##STR00058## GE18 438.81 C.sub.30H.sub.62O
##STR00059## GE20 354.65 C.sub.24H.sub.50O ##STR00060## GE21 382.71
C.sub.26H.sub.54O ##STR00061## GE22 410.76 C.sub.28H.sub.58O
##STR00062## GE23 382.71 C.sub.26H.sub.54O ##STR00063## SE1 452.84
C.sub.31H.sub.64O ##STR00064## SE2 396.43 C.sub.27H.sub.56O
##STR00065## TE1 466.87 C.sub.32H.sub.66O ##STR00066## Farnesene-
derived ether 396.73 C.sub.27H.sub.56O ##STR00067##
[0294] The following properties of the base stocks were tested:
[0295] Kinematic viscosity at 100.degree. C. (KV100) and kinematic
viscosity at 40.degree. C. (KV40) were tested according to ASTM
D7279.
[0296] Viscosity index (VI) was calculated according to ASTM
D2270.
[0297] Pour point was determined according to ASTM D7346.
[0298] Differential scanning calorimetry (DSC) oxidation onset
temperature was tested using a method which was based on ASTM E2009
(method B). According to the method, the base stocks were heated
from 50.degree. C. to 300.degree. C., at a rate of 50.degree.
C./minute, under a pressure of 500 psi in an aluminium SFI pan. The
temperature at which an exotherm was observed was recorded.
[0299] Noack volatility was measured using a method which was based
on IP 393 and was considered similar to CEC-L-40-A-93. According to
the method, reference oils of known Noack volatility were heated
from 40.degree. C. to 550.degree. C. to determine the temperature
at which the Noack volatility weight loss of each of the reference
oils was reached. The base stocks were subjected to the same
process as the reference oils. The Noack weight of the base stocks
could be determined based on the results obtained from the
reference oils.
[0300] The results of the tests are summarized in Table 4, together
with results obtained from conventional base stocks (Durasyn 162, a
group IV base stock; Durasyn 164, a group IV base stock; Yubase 3,
a group II base stock; Yubase 4, a group III base stock; Yubase 4
Plus, a group III base stock; Nexbase 3020, a group II base stock;
Nexbase 3030, a group II base stock; Nexbase 3043, a group III base
stock; and Chevron 100RLV, a group II base stock). Results obtained
from the farnesene-derived ether base stock are also shown for
reference.
TABLE-US-00004 TABLE 4 KV100 KV40 Pour Point DSC Oxidation Noack
(cSt) (cSt) VI (.degree. C.) Onset T (.degree. C.) (% by weight)
GE1 3.3 13.0 125 -42 201.26 5.9 GE2 3.5 13.7 145 -36 205.74 5.1 GE3
3.9 16.0 143 -42 202.89 2.4 GE4 3.3 11.9 146 -27 213.37 3.9 GE5 2.5
8.2 136 -60 203.87 17.9 GE6 3.8 14.6 166 -12 212.71 2.0 GE7 4.0
16.5 144 -36 206.26 6.8 GE8 2.3 7.7 111 -66 213.95 44.9 GE9 3.8
14.9 160 -15 208.17 2.5 SE1 2.7 9.6 123 -18 195.37 12.9 SE2 2.5 9.0
101 -45 183.21 51.8 TE1 3.6 14.9 133 -- 212.91 6.8 Durasyn 162 1.7
5.2 92 -72 223.61 99.6 Durasyn 164 4.0 17.8 126 -75 221.31 18.8
Yubase 3 3.0 14.1 105 -36 220.74 38.6 Yubase 4 4.2 19.2 126 -12
220.00 11.7 Yubase 4 Plus 4.2 18.4 138 -18 220.32 11.6 Nexbase 3020
2.2 7.6 93 -51 221.66 81.9 Nexbase 3030 3.0 12.0 101 -39 221.05
36.8 Nexbase 3043 4.3 19.9 124 -18 222.09 13.2 Chevron 4.6 22.6 119
-15 225.86 13.2 110RLV Farnesene- 3.2 11.6 152 -36 222.26 14.1
derived ether
[0301] A graph of volatility against pour point for ether base
stocks GE1-GE9, SE1, SE2 and TE1 and the conventional base stocks
is shown in FIG. 1. It can be seen that the Guerbet-derived base
stock ethers have a low volatility for a given pour point compared
to conventional base oils. Moreover, the Guerbet-derived base
stocks in which both sides of the ether are branched exhibit
unexpected improvements in pour point as compared to
Guerbet-derived base stocks of comparable carbon number in which
only one side of the ether is branched, without any significant
loss of volatility.
[0302] A graph of volatility against kinematic viscosity at
100.degree. C. for ether base stocks GE1-GE9, SE1, SE2 and TE1 and
the conventional base stocks is shown in FIG. 2. It can be seen
that the Guerbet-derived base stocks and the secondary and tertiary
ether base stocks exhibit both low volatility and low viscosity as
compared to conventional base oils.
[0303] Cold-cranking simulator (CCS) analysis of Guerbet-derived
base stocks GE2 and GE3 was also carried out according to ASTM
D5293. A graph of volatility against cold-cranking simulator
viscosity is shown in FIG. 3. For comparison, data obtained from
conventional hydrocarbon base stocks having a KV100 of from 2.6 to
4.2 is also shown. It can be seen that the Guerbet-derived ethers
exhibit excellent CCS viscosity, as well as low volatility.
Example 2: Properties of Lubricant Compositions Containing Ether
Base Stocks
[0304] Guerbet-derived ether base stocks GE2 and GE3 were blended
with conventional base oil additives (additive A, a commercially
available additive package; additive B, a cold-flow improver;
additive C, an oxidation inhibitor; and additive D, a viscosity
index improver) and conventional base oils (Yubase 4, a group III
base oil; and Yubase 6, a group III base oil) to form lubricant
blends. A Baseline blend and a farnesene-derived ether blend were
also prepared. Yubase 4 was chosen as the main component of the
Baseline blend, since it exhibits a similar KV100 to
Guerbet-derived ether base stock, GE3. The Baseline blend was
believed to be a stringent baseline for comparison, since it is a
5W-30 formulation which meets certain specifications (ACEA A5/B5,
API-SN/GF-4). The details of the blended compositions are shown in
Table 5 in % by weight.
TABLE-US-00005 TABLE 5 Baseline GE2 GE3 Farnesene- blend blend
blend derived blend Additive A 16.4 16.4 16.4 16.4 Additive B 0.15
0.15 0.15 0.15 Additive C 0.1 0.1 0.1 0.1 Additive D 4 4 4 4 Yubase
4 67.45 30.47 17.45 17.45 Yubase 6 11.9 11.9 11.9 11.9 GE2 0 36.98
0 0 GE3 0 0 50 0 Farnesene-derived ether 0 0 0 50
[0305] No problems with miscibility were encountered during
preparation of the blended compositions.
[0306] The blended compositions were tested to see whether the
advantageous properties of the base stocks would be reflected in a
fully formulated lubricant composition. The following properties
were tested:
[0307] Kinematic viscosity at 100.degree. C. (KV100) and kinematic
viscosity at 40.degree. C. (KV40) were tested according to ASTM
D445 (part of SAE J300).
[0308] Viscosity index (VI) was calculated according to ASTM
D2270.
[0309] Cold-cranking simulator (CCS) analysis was carried out at
-30.degree. C. according to ASTM D5293 (part of SAE J300).
[0310] High temperature high shear (HTHS) analysis was carried out
according to CEC-L-36-A-90.
[0311] Total base number (TBN) was determined according to ASTM
D2896.
[0312] Noack volatility was tested according to CEC-L-40-A-93.
[0313] Sulphated ash content was measured according to IP 163.
[0314] The results of the tests are summarized in Table 6.
TABLE-US-00006 TABLE 6 Baseline GE2 GE3 Farnesene- blend blend
blend derived blend KV40 (cSt) 53.59 48.26 44.63 38.57 KV100 (cSt)
9.542 9.105 8.688 7.877 VI 164 173 177 181 CCS -30.degree. C. (cP)
4656 2608 2702 2010 HTHS (cP) 2.98 2.85 2.75 2.62 TBN (mg KOH/g)
11.66 11.29 11.44 10.88 NOACK (% by weight) 11.2 7.7 9.7 14.9
Sulphated ash (%) 1.22 1.26 1.27 1.20
[0315] It can be seen that the properties of the Guerbet-derived
base stocks are also exhibited in the blended compositions. In
particular, beneficial viscosity, volatility and cold-flow
properties are observed. The Guerbet-derived base stocks also
exhibited similar HTHS measurements, TBNs and sulphated ash
contents to the Baseline blend.
Example 3: Engine Performance of Lubricant Compositions Containing
Ether Base Stocks
[0316] The blended compositions from Example 2 were subjected to a
TU-5 JP engine test run according to CEC-L-88-02 (part of ACEA A, B
and C sequences) in order to determine the oxidative stability of
the compositions by assessment of viscosity increases, as well as
piston cleanliness and piston ring sticking. The temperature in the
oil gallery was controlled to 150.degree. C. for the duration of
the test. The results of the TU-5 JP engine tests for the Baseline,
GE2 and GE3 lubricant compositions are shown in Table 7.
[0317] The blended compositions from Example 2 were also subjected
to MRV testing at -35.degree. C. according to ASTM D4684 in order
to gauge low-temperature viscosity characteristics of the
compositions before and after use in the TU-5 JP engine test. The
results of the MRV testing are also shown in Table 7.
TABLE-US-00007 TABLE 7 Baseline GE2 GE3 Limits Absolute viscosity
increase 47.3 27 13.1 .ltoreq.57.3 at 40.degree. C. (mm.sup.2/s)
Viscosity at 40.degree. C. 53.8 45.1 48.2 None 0 hours (mm.sup.2/s)
Viscosity at 40.degree. C. 101.1 72.1 61.3 None 72 hours
(mm.sup.2/s) Overall piston merit (x/10) 8.2 9.2 9.0 .gtoreq.7.6 (5
elements, CRC rating) Ring sticking merit 1st ring 10 10 10
.gtoreq.9 (worst) MRV pre-TU-5 (cP) 21500 7200 7500 Yield stress
pre-TU-5 (Pa) <35 <35 <35 MRV post-TU-5 (cP) 56500 11700
18000 Yield stress post-TU-5 (Pa) <35 <35 <35
[0318] The lubricant compositions containing Guerbet-derived base
stocks passed all aspects of the TU-5 JP engine test.
[0319] A graph of kinematic viscosity at 40.degree. C. against time
is shown in FIG. 4a, and a graph showing the absolute change in
kinematic viscosity at 40.degree. C. after 60 hours is shown in
FIG. 4b. For comparison, results obtained from the
Farnesene-derived blend from Example 2 are also shown. It can be
seen that the increase in viscosity of the lubricant compositions
containing Guerbet-derived base stocks or the Farnesene-derived
blend were significantly lower than or similar to that of the
Baseline composition, with the results obtained from the
Guerbet-derived ether being particularly good. The results indicate
that the lubricant compositions containing ether base stocks
exhibit superior oxidative stability.
[0320] A graph showing the overall piston merit is shown in FIG. 5.
It can be seen that the lubricant compositions containing
Guerbet-derived base stocks had overall high piston merits score,
indicating that these blends exhibit good piston cleanliness
performance.
[0321] The MRV results further demonstrate the excellent
low-temperature viscosity characteristics of lubricant compositions
containing Guerbet-derived base stocks before and after their
use.
Example 4: Engine Compatibility of Lubricant Compositions
Containing Ether Base Stocks
[0322] The blended formulation of GE3 from Example 2 was subjected
to Mercedes EAM and ACEA RE2 seal tests (test methods VDA 675301
and CEC-L-39-96, respectively) to determine the compatibility of
the ether base stocks with typical seals that are found in engines.
An ethylene acrylic rubber is used in the EAM test, whilst an
acrylic-based rubber is used in the RE2 test. The results of the
Mercedes EAM and ACEA RE2 seal tests are shown in Table 8.
TABLE-US-00008 TABLE 8 Baseline GE3 Pass Limits AEM Seal Tensile
strength 9.5 3.4 > -35 Test (Mpa % variation) Elongation Rupture
-18.6 -26.9 > -50 (% variation) Hardness 3 5 10 to -5
(Variation, points) Relative volume change 2.5 0.3 15 to -5 (%)
ACEA Tensile Strength 2 2 18 to -15 RE2 (% variation) Elongation
Rupture -32 -35 10 to -35 (% variation) Hardness 7 3 8 to -5
(Variation, points) Relative volume change 0.6 0.6 5 to -7 (%)
[0323] It can be seen that the lubricant composition containing a
Guerbet-derived base stock passed both of the seal tests,
indicating that the ether base stocks are suitable for use in
engines.
Example 5: Engine Fuel Consumption Performance of Lubricant
Compositions Containing Ether Base-Stocks
[0324] Another blended formulation of GE3 and the baseline blend
were subjected to an M111 fuel economy test according to
CEC-L-054-96 (part of the ACEA A and B sequences) in order to
determine the fuel consumption performance of engines run on ether
base-stocks. The results are given below in table 9 and are quoted
as percentage improvement over the RL191 15W-40 baseline oil
commonly used for such assessments. Accordingly, the results
reported as "Baseline" below recite the percentage performance of
the Baseline blend (5W-30 formulation mentioned above) over the RL
191 15W-40 standard.
TABLE-US-00009 TABLE 9 Baseline GE3 Pass Limits Fuel Economy 2.89%
3.19% >2.5% Improvement relative to RL191 15W-40
[0325] It can be seen that the lubricant containing a
Guerbet-derived base stock passed the fuel economy test and showed
an improvement over the baseline lubricant composition, indicating
that the ether base stocks offer a fuel economy benefit.
* * * * *