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Patent 2532964 Summary

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(12) Patent: (11) CA 2532964
(54) English Title: TRANSMISSION LUBRICATING COMPOSITIONS WITH IMPROVED PERFORMANCE, CONTAINING ACID/POLYAMINE CONDENSATION PRODUCT
(54) French Title: COMPOSITIONS DE LUBRIFICATION POUR TRANSMISSIONS AVEC PERFORMANCES AMELIOREES, CONTENANT UN PRODUIT DE CONDENSATION D'ACIDE/POLYAMINE
Status: Granted
Bibliographic Data
(51) International Patent Classification (IPC):
  • C10M 157/10 (2006.01)
  • C10M 133/16 (2006.01)
  • C10M 133/46 (2006.01)
  • C10M 133/56 (2006.01)
  • C10M 137/02 (2006.01)
  • C10M 139/00 (2006.01)
(72) Inventors :
  • SUMIEJSKI, JAMES L. (United States of America)
  • SMOGGIE, JOHN C. (United States of America)
  • TIPTON, CRAIG (United States of America)
(73) Owners :
  • THE LUBRIZOL CORPORATION (United States of America)
(71) Applicants :
  • THE LUBRIZOL CORPORATION (United States of America)
(74) Agent: SMART & BIGGAR LP
(74) Associate agent:
(45) Issued: 2012-09-18
(86) PCT Filing Date: 2004-06-29
(87) Open to Public Inspection: 2005-02-03
Examination requested: 2009-06-26
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/US2004/020856
(87) International Publication Number: WO2005/010134
(85) National Entry: 2006-01-13

(30) Application Priority Data:
Application No. Country/Territory Date
10/621,154 United States of America 2003-07-16

Abstracts

English Abstract




A lubricating composition comprises (a) an alkyl phosphite, wherein the
alkyl group contains 14 to 20 carbon atoms; (b) a condensation product of a
fatty acid with a polyamine or an alkylenepolyamine; (c) a borate ester; (d) a

borated dispersant; and (e) an oil of lubricating viscosity. The lubricating
composition has improved wear resistance, and further provides anti-shudder
properties and appropriate friction properties. The lubricating composition
can
be used in automatic transmission fluids.


French Abstract

Cette invention se rapporte à une composition lubrifiante contenant (a) un phosphite d'hydrocarbyle ; (b) le produit de la condensation d'au moins un acide gras avec une polyamine ; (c) un ester de borate ; (d) un dispersant boraté ; et (e) une huile de viscosité lubrifiante. Cette invention concerne en outre utilisation de cette composition dans des transmissions automobiles.

Claims

Note: Claims are shown in the official language in which they were submitted.




CLAIMS:

1. A composition comprising:
(a) an alkyl phosphite, wherein the alkyl group contains 14-20 carbon atoms;
(b) a condensation product of a fatty acid with a polyamine;

(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.

2. The composition of claim 1, wherein the condensation product of a fatty
acid
with a polyamine comprises (a) a hydrocarbyl imidazoline represented by the
formula:

Image
wherein R7 is a hydrocarbyl group containing 10 or more carbon atoms; and R8
is derived from alkylenepolyamines; or (b) a hydrocarbyl amide represented by
the formula:

Image
wherein R9 is a hydrocarbyl group containing 10 or more carbon atoms and R10
is derived from alkylenepolyamines.

3. The composition of claim 1, borate ester is prepared by the reaction of a
boron
compound and at least one compound selected from epoxy compounds, alcohols or
mixtures thereof.

4. The composition of claim 1, wherein the borated dispersant is derived from
an N-
substituted alkenyl succinimide represented by the formula:


29



Image
or the formula:

Image
wherein each R30 is independently an alkyl group; each R31 is an alkylene
group,
and X is 1 to 20.

5. The composition of claim 1, wherein the oil of lubricating viscosity is se-
lected from the group consisting of API Group II, III, IV oil and mixtures
thereof.

6. The composition of claim 1, wherein the oil of lubricating viscosity is
present
in an amount less than 50 weight percent, to form a concentrate.

7. A composition of any one of claims 1 to 6, further comprising:
(f) a borate ester represented by the formula:

Image
wherein R11, R12, and R13 are all hydrocarbyl groups containing 1 to 8 carbon
atoms, provided the total number of carbon atoms in R11, R12, and R13 is 4 or
more, further provided that the borate ester (f) contains at least 2
fewer carbons atoms than the borate ester of component (c).




8. The composition of claim 1, wherein the polyamine is an alkylenepolyamine
selected from the group consisting of ethylenepolyamines, propylenepolya-
mines, butylenepolyamines and mixtures thereof, and wherein the condensation
product of a fatty acid with the alkylenepolyamine comprises at least one
compound selected from the group consisting of hydrocarbyl amides, and
hydrocarbyl imidazolines.

9. A method of lubricating an automatic transmission system, comprising
supplying thereto a lubricant comprising the composition of claim 1.

10. A composition comprising:
(a) an alkyl phosphite, wherein the alkyl group contains 14-20 carbon atoms;
(b) a condensation product of a fatty acid with an alkylenepolyamine
selected from the group consisting of ethylenepolyamines, butylene-
polyamines and mixtures thereof, wherein the condensation product
comprises at least one compound selected from the group consisting of
hydrocarbyl amides and hydrocarbyl imidazolines;
(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.


31

Description

Note: Descriptions are shown in the official language in which they were submitted.



CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
Case No. 3218
TITLE
Transmission Lubricating Compositions with Improved Performance, Contain-
ing Acid/Polyamine Condensation Product
FIELD OF INVENTION
[0001] The present invention relates to an oil of lubricating viscosity con-
taining the condensation product of a polyamine and an acid, a hydrocarbyl
phosphite and boron containing compounds. The composition has improved
wear properties. The composition can be used in automatic transmission fluids.
BACKGROUND OF THE INVENTION
[0002] It is known to add various additives to an oil of lubricating viscosity
for automatic transmission fluids (hereinafter referred to as ATF) to improve
resistance to wear, decrease anti-shudder properties and provide the
appropriate
friction properties. Friction properties of an ATF have to be balanced to
provide
high dynamic torque for efficient clutch engagement capacity and high static
friction for good clutch holding. The ATF also has to provide a positive
friction
versus speed curve slope for good anti-shudder durability. These competing
requirements are difficult to balance. In addition antiwear properties need to
be
sufficient for gear durability.
[0003] In an effort to overcome these issues vehicle manufacturers have
defined specifications; for example, The Ford Motor Company have the MER-
CONOV specification. These specifications highlight a number of tests that
ATF's and other lubricating oil compositions should satisfy. For ATF's to
satisfy wear requirements, to decrease anti-shudder properties and to have the
appropriate friction properties, important tests include "The Ford/Greening
Low
Speed Friction Test", "The Timken Wear Test" and "The Ford Clutch Friction
Durability Test." Many known lubricating oil compositions for ATF systems
successfully pass one or two of the named tests above. From an automotive
manufacturers perspective it would be desirable to have one composition capa-
ble of passing all three of the above named tests.
[0004] US Patent 6,482,777 discloses a lubricating composition for a trans-
mission package containing at least one saturated fatty phosphate ester or
salt


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
and optionally either at least one fatty acid imidazoline or the reaction
product
of a fatty acid and polyalkylene polyamine and/or a borated dispersant,
wherein
the lubricating composition is free of saturated fatty phosphites. The composi-

tion exhibits improved friction properties and optionally improved thermal
stability.

[0005] US 5,759,965 discloses the combination of boron containing over-
based materials, borated epoxides, borated dispersants, a variety of
phosphorus
acid esters and derivatives thereof and an oil of lubricating viscosity.
[0006] US 6,528,458 disclose the combination of 2,5-dimercapto-1,3,4-
thiadiazole, imidazoline, borated epoxides and short chain phosphites and, in
a
different example, borated dispersants.
[0007] US Patent 6,103,673 discloses a composition containing at least 0.1
wt% of an overbased metal salt and contributing 0.5 to 10 total base number
(TBN) to the composition, at least 0.1 wt% of a phosphorus compound, 0.1 to
0.25 wt% of a combination of friction modifiers selected from zinc salts of
fatty
acids with at least 10 carbon atoms, hydrocarbyl imidazolines containing at
least
12 carbon atoms in the hydrocarbyl group and borated epoxides.
[0008] US Patent application 2002/0151441 discloses an automatic transmis-
sion fluid containing at least 0.1 wt% of a metal detergent, a dispersant, a
mixture of at least two friction modifiers and a base oil. The composition
exhibits anti-shudder properties and friction durability.
[0009] It would be desirable to have compositions with improved wear
resistance. The invention further provides anti-shudder properties and the
appropriate friction properties. The invention further provides compositions
suitable for use in a variety of automatic transmission fluids.
SUMMARY OF THE INVENTION
[0010] The present invention provides a composition comprising:
(a) a hydrocarbyl phosphite;
(b) a condensation product of a fatty acid with a polyamine;
(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.
2


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WO 2005/010134 PCT/US2004/020856
[0011] The invention further provides a process for preparing a composition
mixing:
(a) a hydrocarbyl phosphite;
(b) a condensation product of a fatty acid with a polyamine;
(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.
[0012] The invention further provides compositions with improved wear
resistance, improved anti-shudder properties, and the appropriate friction
dura-
bility. The invention further provides compositions suitable for use in a
variety
of power transmissions, especially automatic transmission fluids.
DETAILED DESCRIPTION OF THE INVENTION
[0013] As used herein, the term "hydrocarbyl substituent" or "hydrocarbyl
group" is used in its ordinary sense, which is well-known to those skilled in
the
art. Specifically, it refers to a group having a carbon atom directly attached
to
the remainder of the molecule and having predominantly hydrocarbon character.
Examples of hydrocarbyl groups include:
[0014] hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl),
alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-,
aliphatic-,
and alicyclic-substituted aromatic substituents, as well as cyclic
substituents
wherein the ring is completed through another portion of the molecule (e.g.,
two
substituents together form a ring);
[0015] substituted hydrocarbon substituents, that is, substituents containing
non-hydrocarbon groups which, in the context of this invention, do not alter
the
predominantly hydrocarbon nature of the substituent (e.g., halo (especially
chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso,
and sulfoxy);
[0016] hetero substituents, that is, substituents which, while having a pre-
dominantly hydrocarbon character, in the context of this invention, contain
other
than carbon in a ring or chain otherwise composed of carbon atoms. Heteroa-
toms include sulfur, oxygen, nitrogen, and encompass substituents as pyridyl,
furyl, thienyl and imidazolyl. In general, no more than two, preferably no
more
3


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
than one, non-hydrocarbon substituent will be present for every ten carbon
atoms in the hydrocarbyl group; typically, there will be no non-hydrocarbon
substituents in the hydrocarbyl group.
[0017] The present invention provides a composition comprising:
(a) a hydrocarbyl phosphite;
(b) the condensation product of at least one fatty acid with a polyamine;
(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.
Hydrocarbyl Phosphite

[0018] The hydrocarbyl phosphite of the invention can be represented by the
formula:

R1-O\ /H

P\ (I)
R2-O~ O

wherein at least one of R1 and R2 is a hydrocarbyl group containing at least 8
carbon atoms and the other can be hydrogen or a hydrocarbyl group; preferably
both R1 and R2 are hydrocarbyl groups. The hydrocarbyl groups can be alkyl,
cycloalkyl, aryl, acyclic or mixtures thereof. The hydrocarbyl group can be
alkyl with 8 to 40, preferably 10 to about 35, more preferably 12 to 30, even
more preferably 13 to 25, and even more preferably 14 to 20 carbon atoms.
[0019] Alkyl groups can be linear or branched, preferably linear, and satu-
rated or unsaturated, preferably saturated. Examples of alkyl groups suitable
for
R1 and R2 include octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl,
tridecyl,
tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, octadecenyl, nonode-
cyl, eicosyl or mixtures thereof. In one embodiment R1 and R2 each have 16 to
18 carbon atoms.
[0020] The hydrocarbyl phosphite is typically present at 0.01 to 5, preferably
0.03 to 1, and more preferably 0.05 to 0.7 and even more preferably 0.1 to 0.4
weight percent of the lubricating oil composition.

4


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WO 2005/010134 PCT/US2004/020856
The Condensation Product of a Fatty Acid with a Polyamine
[0021] The condensation of a fatty acid and a polyamine of the invention
typically result in the formation of at least one compound selected from hydro-

carbyl amides, hydrocarbyl imidazolines and mixtures thereof. In one embodi-
ment the condensation products are hydrocarbyl imidazolines. In one embodi-
ment the condensation products are hydrocarbyl amides. In one embodiment the
condensation products are mixtures of hydrocarbyl imidazolines and hydrocar-
byl amides. Preferably the condensation product is mixtures of hydrocarbyl
imidazolines and hydrocarbyl amides.
[0022] The fatty acid of the invention can be derived from a hydrocarbyl
carboxylic acid. The hydrocarbyl group can be alkyl, cycloalkyl, or aryl, al-
though alkyl is preferred, and the hydrocarbyl groups can be linear or
branched.
Typically the fatty acid contains 8 or more, preferably 10 or more, more pref-
erably 13 or more and even more preferably 14 or more carbon atoms (including
the carbon of the carboxy group). Typically the fatty acid contains 8 to 30,
preferably 12 to 24 and even more preferably 16 to 18 carbon atoms. Other
suitable carboxylic acids can include the polycarboxylic acids or carboxylic
acids or anhydrides having from 2 to 4 carbonyl groups, preferably 2. The
polycarboxylic acids can include succinic acids and anhydrides and Diels-Alder
reaction products of unsaturated monocarboxylic acids with unsaturated carbox-
ylic acids (such as acrylic, methacrylic, maleic, fumaric, crotonic and
itaconic
acids). Preferably, the fatty carboxylic acids are fatty monocarboxylic acids
containing 8 to 30, preferably 10 to 26 and even more preferably 12 to 24
carbon atoms.
[0023] Examples of suitable fatty acids can include caprylic acid, capric
acid, lauric acid, myristic acid, palmitic acid, stearic acid, eicosic acid
and, tall
oil acids. Preferably the fatty acid is stearic acid, which can be used alone
or in
combination with other fatty acids.
[0024] The polyamines of the invention can be acyclic or cyclic, preferably
acyclic; and linear or branched, preferably linear.
[0025] In one embodiment the polyamines can be alkylenepolyamines
selected from the group consisting of ethylenepolyamines, propylenepoly-
5


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
amines, butylenepolyamines and mixtures thereof. Examples of propylenepoly-
amines can include prop ylene di amine and dipropylenetriamine.
[0026] Particularly preferred ethylenepolyamines are selected from the group
consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetra-

ethylenepentamine, pentaethylenehexamine, N-(2-aminoethyl)-N'-[2-[(2-
aminoethyl)amino] ethyl]- 1,2-ethanediamine, polyamine still bottoms and
mixtures thereof.

[0027] In one embodiment the polyamines can be a,(3-diamino alkanes.
Suitable a,(3-diaminoalkanes can include diaminopropanes, diaminobutanes or
mixtures thereof. Specific diaminoalkanes are selected from the group consist-
ing of N-(2-aminoethyl)- 1,3 -propane diamine, 3,3'-diamino-N-
methyldipropylamine, tris(2-aminoethyl)amine, N,N-bis(3-aminopropyl)-1,3-
propane diamine, N,N'-1,2-ethanediylbis-(1,3-propane diamine) and mixtures
thereof.
[0028] In one embodiment other polyamines can include
di-(trimethylene)triamine, piperazine, diaminocyclohexanes and mixtures
thereof.

[0029] In one embodiment the polyamine can be cyclic and can include, but
are not limited to, compounds that are represented by the formula:

(R3) N (R4)_N\ R5
6 (II)
111~j R6

wherein R3 represents a carbocyclic or heterocyclic group containing atoms
bonded to form mono- or poly- nuclear rings; and the atoms are selected from
the group consisting of carbon, oxygen, nitrogen, phosphorus and mixtures
thereof. Preferably R3 can be atoms selected from the group consisting of
carbon, oxygen, nitrogen and mixtures thereof.
[0030] The mononuclear cyclic structure typically contains 5 to 8 atoms and
preferably 6 to 7 atoms. The polynuclear cyclic structure contains 8 to 16 and
preferably 10 to 12 atoms. In formula (II), R3 can contain 4 to 15, preferably
5
6


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
to 11, more preferably 5 to 8 atoms. The cyclic ring can be aromatic, non-
aromatic or mixtures thereof, although non-aromatic is preferred.
[0031] R4 can be a hydrocarbyl group, typically an alkyl or alkenyl group
containing 1 to 8, preferably 1 to 6, and even more preferably 2 to 5 carbon
atoms. The alkyl or alkenyl group can be substituted, unsubstituted, branched,
unbranched alkylaryl, cycloalkyl or mixtures thereof. Suitable examples of R4
can include ethyl, propyl, butyl and pentyl. Preferably R4 is ethyl, propyl or
mixtures thereof.
[0032] R5 and R6 can be, hydrogen or hydrocarbyl; preferably at least one,
and even more preferably both of R5 and R6 are hydrogen. When R5 and R6 are
hydrocarbyl, the number of carbon atoms present in each of R5 and R6 is inde-
pendently is in the range from 1 to 8, preferably 1 to 5 and even more
preferably
1 to 3. Suitable examples of hydrocarbyl groups can include methyl, ethyl,
propyl, butyl and pentyl.
[0033] Examples of suitable cyclic polyamines include 4-(3-aminopropyl)
morpholine, 4-(3-aminoethyl) morpholine or mixtures thereof. Preferably the
cyclic amine is 4-(3-aminopropyl) morpholine, which, may be used alone or in
combination with other polyamines.
[0034] Typically the hydrocarbyl imidazolines formed by a condensation product
of a fatty acid with a polyamine can be represented by the formula:

11 :---",> (III)
R7--- N . R8

wherein R7 can be a hydrocarbyl group, preferably a linear or branched alkyl
group, preferably linear; and the hydrocarbyl group can be saturated or unsatu-

rated, preferably saturated. Typically the hydrocarbyl group R7 can contain 8
or
more, preferably 11 or more, preferably 14 or more and more preferably 16 or
more carbon atoms. For example the hydrocarbyl group can contain 10 to 30,
preferably 12 to 24 and more preferably 16 to 18 carbon atoms. In one embodi-
ment the hydrocarbyl group contains 17 carbon atoms. R8 can be is a hydrocar-
byl group or a substituted hydrocarbyl group. In one embodiment, R8 is derived
from alkylenepolyamines discussed above.
7


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
[0035] Typically the hydrocarbyl amides formed by a condensation product of a
fatty acid with a polyamine can be represented by the formula:
O

H (IV)
R9 N_~, R1

wherein R9 can be a hydrocarbyl group of the type defined for R7 above. R10
can be hydrogen, a hydrocarbyl group or a substituted hydrocarbyl group. In
one embodiment, R10 is derived from alkylenepolyamines discussed above.
[0036] The condensation product of a fatty acid and a polyamine is typically
present at 0.01 to 3, preferably 0.03 to 1, and more preferably 0.05 to 0.6
and
even more preferably 0.07 to 0.3 weight percent of the lubricating oil composi-

tion.
Borate Ester
[0037] The invention further contains a borate ester. The borate ester can be
prepared by the,reaction of a boron compound and at least one compound
selected
from epoxy compounds, halohydrin compounds, epihalohydrin compounds, alcohols
and mixtures thereof. Typically the alcohols include monohydric alcohols,
dihydric
alcohols, trihydric alcohols or higher alcohols. Hereinafter "epoxy compound
or
equivalent" is used when referring to "at least one compound selected from
epoxy
compounds, halohydrin compounds, epihalohydrin compounds, alcohols and mix-
tures thereof."
[0038] Boron compounds suitable for preparing the borate ester include the
various forms selected from the group consisting of boric acid (including meta-

boric acid, HBO2, orthoboric acid, H3B03, and tetraboric acid, H2B407), boric
oxide, boron trioxide and alkyl borates. The borate ester can also be prepared
from boron halides.
[0039] The borate ester formed by the reaction of a boron compound and an
epoxy compound or equivalent can be represented by at least one formula
selected from:

8


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
R12-O
B O R11 (V)
R13-p/

or
R140 OR15
R 17OB - O-B- OR16 (VI)
or
C1R18
IB

O/ O (VII)
82 I
00-B B-OR19
0

or
H
R21 O OQ

BE) (VIII)
O O
R22
or
OH
O B\O (IX)
R23
or

OR25 R
HO
B
O~ p O~ B O OH (X)
n
R24 OR27 R26
9


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WO 2005/010134 PCT/US2004/020856
wherein R11, R12 and R13 can be hydrogen or hydrocarbyl groups provided at
least one, preferably at least two of R11, R12 and R13 are hydrocarbyl groups.
In
one embodiment, R11 is a hydrocarbyl group; and R12 and R13 are hydrogen. In
one embodiment, R11 and R12 are hydrocarbyl groups and R13 is hydrogen. In
one embodiment R11, R12 and R13 are all hydrocarbyl groups. The hydrocarbyl
groups can be alkyl, aryl or cycloalkyl when any 2 adjacent R groups are con-
nected in a ring. When alkyl, the group can be saturated or unsaturated,
unsatu-
rated being preferred. In one embodiment the hydrocarbyl group is cyclic. In
one embodiment the hydrocarbyl groups are mixtures of alkyl and cycloalkyl.
[0040] Typically there is no upper limit on the number of carbon atoms, but
a practical limit is 500, preferably 400, more preferably 200, even more
prefera-
bly 100 or 60. For example the number of carbon atoms present in R11, R12 and
R13 can be 1 to 60, preferably 1 to 40 and more preferably 1 to 30 carbon
atoms,
provided the total number of carbon atoms in R11, R12 and R13 is 9 or more,
preferably 10 or more, more preferably 12 or more or 14 or more.
[0041] In one embodiment R11, R12 and R13 are all hydrocarbyl groups
containing 1 to 30 carbon atoms, provided the total number of carbon atoms in
R11, R12 and R13 is 9 or more.

[0042] R14 to R20 inclusive can be hydrogen or hydrocarbyl groups, provided
at least one of R14 to R17 and/or R18 to R20 is a hydrocarbyl group. R21 to
R26
inclusive are hydrocarbyl groups or hydrogen, although hydrocarbyl groups are
preferred; and R27 can be hydrogen or a hydrocarbyl group, although hydrogen
is preferred. The hydrocarbyl group definition for R14 to R27 inclusive is the
same as the definition given for R11, R12 and R13

[0043] Examples of groups suitable for R11 to R 27 inclusive include isopro-
pyl, n-butyl, isobutyl, amyl, 2-pentenyl, 4-methyl-2-pentyl, 2-ethyl-l-hexyl,
2-
ethylhexyl, heptyl, isooctyl, nonyl, decyl, undecyl, dodecenyl, dodecyl,
tridecyl,
tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and
eicosyl
groups.
[0044] The epoxy compounds useful for preparing the borate ester of the inven-
tion can be represented by the formulae:



CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
R29
O
H T (XIa)
R28

or
R29
O
(XIb)
28
R

wherein R28 can be an alkyl chain containing 8 to 30, preferably 10 to 26 and
even more preferably 12 to 22 carbon atoms; R29 can be hydrogen or an alkyl
chain containing 1 to 4, preferably 1 to 2 carbon atoms, even more preferably
R29 being hydrogen; and T can be hydrogen or a halogen, that is, chlorine,
bromine, iodine or fluorine or mixtures thereof, although chlorine is
preferred.
Even more preferably T is hydrogen. When T is a halogen, the epoxy compounds
of the invention are epihalohydrin compounds.
[0045] In one embodiment the epoxy compounds of the invention include
commercial mixtures of C14-C16 epoxides or C14-C18 epoxides. In one
embodiment,
the epoxy compounds of the invention have been purified. Examples of suitable
purified epoxy compounds can include 1,2-epoxydecane, 1,2-epoxyundecane,
1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxybutadecane, 1,2-epoxypenta-
decane 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane,
1,2-epoxynonadecane and 1,2-epoxyicosane. Preferably purified epoxy compounds
include 1,2-epoxytetradecane, 1,2-epoxypentadecane 1,2-epoxyhexadecane,
1,2-epoxyheptadecane, 1,2-epoxyoctadecane; and more preferably 1,2-epoxy-
hexadecane.
[0046] Another group of compounds described as "epoxy compounds or equiva-
lents" are alcohols and include monohydric alcohols, dihydric alcohols,
trihydric
alcohols, higher alcohols (that is, alcohols containing 4 or more hydroxy
groups) and
mixtures thereof, monohydric alcohols being preferred. Typically the alcohol
compounds contain 2 to 30, more preferably 4 to 26 and even more preferably 6
to 20
11


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carbon atoms. The alcohol compounds can include glycerol compounds such as
glycerol monooleate.
[0047] The borate esters can be prepared by blending the boron compound and
the epoxy compound or equivalent and heating them at a suitable temperature,
typically 80 C to 250 C, more preferably 90 C to 240 C or 100 C to 230 C,
until the desired reaction has occurred. The molar ratio of the boron compound
to the epoxy compound or equivalent is typically 4:1 to 1:4, preferably 1:1 to
1:3, and more preferably about 1:2. An inert liquid can be used in performing
the reaction. The liquid can be, for instance, toluene, xylene, chlorobenzene,
dimethylformamide and mixtures thereof. Water is formed and is typically
distilled off during the reaction. Alkaline reagents can be used to catalyze
the
reaction.
[0048] The borate ester is typically present at 0.01 to 3, preferably 0.03 to
1,
and more preferably 0.05 to 0.6 and even more preferably 0.07 to 0.3 weight
percent of the lubricating oil composition.
[0049] In one embodiment an optional borate ester may be present in the
invention, in addition to the borate ester which has been described above. The
optional borate ester is derived from formula (V) except R", R12 and R13 are
all
hydrocarbyl groups containing 1 to 8, preferably 2 to 7 and even more prefera-
bly 3 to 6 carbon atoms, provided the total number of carbon atoms in R11, R12
and R13 is 4 or more, preferably 6 or more and even more preferably 8 or more,
and further provided that the optional borate ester contains at least 2 fewer
carbon atoms, preferably at least 3 fewer carbon atoms, more preferably at
least
4 fewer carbon atoms and even more preferably at least 5 carbons atoms than
the borate ester of component (c).
[0050] Suitable examples of the optional borate ester include tripropyl
borate, tributyl borate, tripentyl borate, trihexyl borate, triheptyl borate,
trioctyl
borate, trinonyl borate and tridecyl borate.
[0051] In one embodiment the optional borate ester is selected from the
group consisting tributyl borate, tri-2-ethylhexyl borate and mixtures
thereof. In
one embodiment the optional borate ester is tributyl borate. In one embodiment
the optional borate ester is tri-2-ethylhexyl borate.
12


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[0052] When present, the optional borate ester is typically present at 0 to 5,
preferably 0.01 to 3, and more preferably 0.05 to 1.5 and even more preferably
0.1 to 0.7 weight percent of the lubricating oil composition.
[0053] The total combined amount of borate ester and the optional borate ester
is
typically 0.01 to 8, preferably 0.04 to 4, and more preferably 0.1 to 2.1 and
even
more preferably 0.17 to 1 weight percent of the lubricating oil composition.
Borated Dispersant
[0054] The invention further includes a borated dispersant typically derived
from N-substituted long chain alkenyl succinimides. The N-substituted long
chain alkenyl succinimides have a variety of chemical structures and two
typical
formulae include:

0
Rao

[,,N[R31 NH}-R31 NH2 (XII)
0
or

0 0
R30 Rao
N-[R31 NH],-R31 N (XIII)

O O

wherein each R30 is independently an alkyl group, frequently a polyisobutyl
group with a molecular weight of 350 to 5000, preferably 500 to 3000, and R31
are alkylene groups, commonly ethylene (C2H4) groups. Each R30 can also be
substituted by additional succinimide functionality and can be attached to the
succinimide structures by a variety of linkages. The number of repeat units
"x"
can be from 1 to 20, preferably 1 to 15 and even more preferably 1 to 10.
[0055] The N-substituted long chain alkenyl succinimides are borated using
a variety of agents selected from the group consisting of the various forms of
boric acid (including metaboric acid, HBO2, orthoboric acid, H3BO3, and
13


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tetraboric acid, H2B407), boric oxide, boron trioxide, and alkyl borates.
These
agents are described in more detail above. In one embodiment the borating
agent is boric acid which can be used alone or in combination with other borat-

ing agents.
[0056] The borate dispersant can be prepared by blending the boron compound
and the N-substituted long chain alkenyl succinimides and heating them at a
suitable temperature, typically 80 C to 250 C, more preferably 90 C to 230 C
and even more preferably 100 C to 210 C, until the desired reaction has oc-
curred. The molar ratio of the boron compounds to the N-substituted long chain
alkenyl succinimides is typically 10:1 to 1:4, preferably 4:1 to 1:3, and even
more preferably 1:2. An inert liquid can be used in performing the reaction.
The
liquid can include but are not limited to toluene, xylene, chlorobenzene, di-
methylformamide and mixtures thereof.
[0057] The borated dispersant is typically present at 0.03 to 6, preferably
0.06
to 3, and more preferably 0.15 to 2 and even more preferably 0.3 to 1.5 wt %
of
the lubricating oil composition.
Oils of Lubricating Viscosity
[0058] The lubricating oil composition of the present invention can be added
to an oil of lubricating viscosity. The oil includes natural and synthetic
oils, oil
derived from hydrocracking, hydrogenation, hydrofinishing, unrefined, refined
and re-refined oils, or mixtures thereof.
[0059] Unrefined oils are those obtained directly from a natural or synthetic
source generally without (or with little) further purification treatment.
[0060] Refined oils are similar to the unrefined oils except they have been
further treated in one or more purification steps to improve one or more
proper-
ties. Purification techniques are known in the art and include solvent
extraction,
secondary distillation, acid or base extraction, filtration, percolation and
the
like.
[0061] Re-refined oils are also known as reclaimed or reprocessed oils, and
are obtained by processes similar to those used to obtain refined oils and
often
are additionally processed by techniques directed to removal of spent
additives
and oil breakdown products.
14


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[0062] Natural oils useful in making the inventive lubricants include animal
oils, vegetable oils (e.g., castor oil, lard oil), mineral lubricating oils
such as
liquid petroleum oils and solvent-treated or acid-treated mineral lubricating
oils
of the paraffinic, naphthenic or mixed paraffinic-naphthenic types and oils
derived from coal or shale or mixtures thereof.
[0063] Synthetic lubricating oils are useful and include hydrocarbon oils
such as polymerised and interpolymerised olefins (e.g., polybutylenes, polypro-

pylenes, propyleneisobutylene copolymers); poly(1-hexenes), poly(1-octenes),
poly(1-decenes), and mixtures thereof; alkyl-benzenes (e.g. dodecylbenzenes,
tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes); polyphenyls
(e.g., biphenyls, terphenyls, alkylated polyphenyls); alkylated diphenyl
ethers
and alkylated diphenyl sulphides and the derivatives, analogs and homologs
thereof or mixtures thereof.
[0064] Other synthetic lubricating oils include but are not limited to liquid
esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl
phos-
phate, and the diethyl ester of decane phosphonic acid), and polymeric tetrahy-

drofurans. Synthetic oils may be produced by Fischer-Tropsch reactions and
typically may be hydroisomerised Fischer-Tropsch hydrocarbons or waxes.
[0065] Oils of lubricating viscosity can also be defined as specified in the
American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
The five base oil groups are as follows: Group I (sulphur content >0.03 wt %,
and/or <90 wt % saturates, viscosity index 80-120); Group II (sulphur content
<0.03 wt %, and >90 wt % saturates, viscosity index 80-120); Group III
(sulphur
content <0.03 wt %, and >90 wt % saturates, viscosity index >120); Group IV
(all polyalphaolefins (PAOs)); and Group V (all others not included in Groups
I,
II, III, or IV). The oil of lubricating viscosity is selected from the group
con-
sisting of API Group I, II, III, IV, V oil and mixtures thereof. Preferably
the oil
of lubricating viscosity is an API Group II, III, or IV oil and mixtures
thereof.
[0066] The oil of lubricating viscosity is typically present at 78 to 99.9,
preferably 89 to 99.8, and more preferably 93.6 to 99.7 and even more prefera-
bly 96.3 to 99.3 weight percent of the lubricating oil composition.



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Performance Additives
[0067] The lubricating oil composition can include other performance
additives selected from the group consisting of metal deactivators,
detergents,
dispersants, antioxidants, antiwear agents, corrosion inhibitors, antiscuffing
agents, extreme pressure agents, foam inhibitors, demulsifiers, friction
modifi-
ers, viscosity modifiers, pour point depressants and seal swelling agents.
Typically a fully-formulated lubricating oil will contain one or more of these
additives.
[0068] The total combined amount of the optional additives present can be 0
to 10, preferably 0.1 to 7, more preferably 0.2 to 5 and even more preferably
1
to 5 weight percent of the lubricating oil composition.
Metal Deactivators
[0069] Metal deactivators can be used to neutralise the catalytic effect of
metal for promoting oxidation in lubricating oil. Examples of metal deactiva-
tors can include derivatives of benzotriazoles, benzimidazoles, 2-alkyldithio-
benzimidazoles, 2-alkyldithiobenzothiazoles, 2-(N,N-dialkyldithiocarbamoyl)-
benzothiazoles, 2,5-bis(alkyl-dithio)-1,3,4-thiadiazoles, 2,5-bis(N,N-dialkyl-
dithiocarbamoyl)-1,3,4-thiadiazoles and 2-alkyldithio-5-mercapto thiadiazoles.
[0070] Preferably the metal deactivator is a hydrocarbyl substituted benzotri-
azole compound. The benzotriazole compounds with hydrocarbyl substitutions
include at least one of the following ring positions 1- or 2- or 4- or 5- or 6-
or
7-. The hydrocarbyl groups contain 1 to 30, preferably 1 to 15, preferably 1
to 7
carbon atoms, and even more preferably the metal deactivator is 5-
methylbenzotriazole (tolyltriazole).
Dispersants
[0071] Dispersants other than the borated dispersants of the invention can
also be added. These often known as ashless-type dispersants because, prior to
mixing in a lubricating oil composition, they do not contain ash-forming
metals,
and they do not normally contribute any ash forming metals when added to a
lubricant and polymeric dispersants. Ashless type dispersants are
characterised
by a polar group attached to a relatively high molecular weight hydrocarbon
chain. Typical ashless dispersants include N-substituted long chain alkenyl
16


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succinimides. Examples of N-substituted long chain alkenyl succinimides
include polyisobutylene succinimide with number average molecular weight 350
to 5000, preferably 500 to 3000. Succinimide dispersants and their preparation
are disclosed, for instance in US Patent 4,234,435. The polyisobutylene suc-
cinimide can be used alone or in combination with other dispersants.
[0072] In one embodiment the invention further comprises at least one
dispersant derived from polyisobutylene, an amine and zinc oxide to form a
polyisobutylene succinimide complex with zinc. The polyisobutylene succinim-
ide complex with zinc can be used alone or in combination with other dispers-
ants.
[0073] Another class of ashless dispersant is Mannich bases. Mannich
dispersants are the reaction products of alkyl phenols in which the alkyl
group
contains at least 30 carbon atoms with aldehydes (especially formaldehyde) and
amines (especially polyalkylene polyamines).
[0074] Dispersants can also be post-treated conventional method by a reac-
tion with any of a variety of agents. Among these are urea, thiourea, dimercap-

tothiadiazoles, carbon disulfide, aldehydes, ketones, carboxylic acids,
hydrocar-
bon-substituted succinic anhydrides, maleic anhydride, nitriles, epoxides,
boron
compounds, and phosphorus compounds.
Detergents
[0075] Detergents are known and can include neutral or overbased, Newto-
nian or non-Newtonian, basic salts of alkali, alkaline earth and transition
metals
with one or more hydrocarbyl sulphonic acid, carboxylic acid, phosphorus acid,
mono- and/or di- thiophosphoric acid, alkyl phenol, sulphur coupled alkyl
phenol compounds, salixarates, saligenins or mixtures thereof. Commonly used
metals include sodium, potassium, calcium, magnesium lithium or mixtures
thereof. Most commonly used metals include sodium, magnesium and calcium.
Detergents and in particular overbased detergents and their preparation are
disclosed in US Patent 3,629,109.
Antiwear Agents
[0076] The lubricating oil composition may additionally contain an antiwear
agent. Useful antiwear agents include zinc hydrocarbyl dithiophosphates,
17


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phosphoric acid esters or salt thereof; phosphites; and phosphorus-containing
carboxylic esters, ethers, and amides or mixtures thereof. Examples of
suitable
zinc hydrocarbyl dithiophosphates compounds can include zinc isopropyl
methylamyl dithiophosphate, zinc isopropyl isooctyl dithiophosphate, barium
di(nonyl)-dithiophosphate, zinc di(cyclohexyl) dithiophosphate, calcium
di(hexyl) dithiophosphate, zinc isobutyl isoamyl dithiophosphate, zinc
isopropyl
n-butyl dithiophosphate, isobutyl primary amyl dithiophosphate, methylamyl
dithiophosphate and isopropyl 2-ethylhexyl dithiophosphate.

Antioxidants
[0077] Antioxidants are known materials and include diphenylamines,
hindered phenols, molybdenum dithiocarbamates and sulphurised olefins.
[0078] Diphenylamine antioxidants can be represented by the formula:
(XIV)
R 32)z (R33)z

wherein R32 and R33 hydrocarbyl groups, preferably arylalkyl or alkyl groups.
The arylalkyl groups contain 6 to 20, preferably 6 to 10 carbons atoms. The
alkyl groups can be linear or branched, preferably linear; the alkyl group con-

tains 1 to 24, preferably 2 to 18 and even more preferably 4 to 12 carbon
atoms;
and z is independently 0, 1, 2, or 3, provided that at least one aromatic ring
contains a hydrocarbyl group. Preferred alkylated diphenylamines can include
octyl diphenylamine, nonyl diphenylamine, bis-octyl diphenylamine and bis-
nonyl diphenylamine.
[0079] Sterically hindered phenols can be represented by the formula:
18


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R34

HO -O E
R35
[0080] wherein R34 and R35 are independently branched or linear alkyl
groups containing 1 to 24, preferably 4 to 18, and even more preferably 4 to
12
carbon atoms; and E is hydrogen, hydrocarbyl, a bridging group linking to a

second aromatic group or mixtures thereof.
[0081] R34 and R35 can be either straight or branched chain; branched is
preferred. Preferably the phenol is butyl substituted containing two t-butyl
groups. When the t-butyl groups occupy the 2,6-positions, the phenol is steri-
cally hindered. Examples of suitable hydrocarbyl groups include 2-ethylhexyl,
n-butyl and dodecyl groups. Examples of suitable bridging groups include
-CH2- (methylene bridge) and -CH2OCH2- (ether bridge).
[0082] When present, the sterically hindered bridged phenols other than
component (a) can be represented by the formulae:
R37
R36

H Y OH (XVI)
R39
R38
or
OH OH
R40 R41
I I (XVII)
R43 R42

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wherein R36, R37, R38, R39, Roo, R41 are either straight or branched chain and
contain 4 to 18, preferably 4 to 12 carbon atoms. Preferably the phenol is
butyl
substituted. R42 and R43 are independently hydrogen or hydrocarbyl; preferably
R42 and R43 are arylalkyl or alkyl groups. The alkyl groups of R42 and R43 can
be linear or branched, linear being preferred. R42 and R43 are preferably in
the
para position. The arylalkyl or alkyl groups typically contain 1 to 15,
preferably
1 to 10, and more preferably 1 to 5 carbon atoms. The bridging group Y can
include -CH2- (methylene bridge) or -CH2OCH2- (ether bridge).
[0083] Examples of methylene-bridged sterically hindered phenols include
4,4 -methylene-bis-(6-tert-butyl o-cresol), 4,4-methylene-bis-(2-tert-amyl-o-
cresol) ,2,2 -methylene-bis-(4-methyl-6-tert-butylphenol) and 4,4-methylene-
bis-(2,6-di-tertbutylphenol). In one embodiment, the sterically hindered
phenols
suitable for the invention can be hindered esters represented by the formula:
R44
HO CH2CH2C(O)OR46 (XVIII)
R45

wherein R44 and R45 are straight or branched alkyl groups that can be
substituted
or unsubstituted, containing 3 to 22, preferably 3 to 18, more preferably 4 to
12
carbon atoms. Specific examples include of alkyl groups di-secondary butyl and
tri-tertiary butyl. R46 can be hydrocarbyl. Suitable examples include 2-
ethylhexyl or n-butyl ester, dodecyl, -CH2CH2COOH and mixtures thereof.
[0084] Suitable examples of molybdenum dithiocarboamates include com-
mercial materials sold under the trade names such as Vanlube 822TM and Moly-
vanTM A from R. T. Vanderbilt Co., Ltd., and Adeka Sakura-LubeTM S-100 and
S-165 and S-600 from Asahi Denka Kogyo K. K.
[0085] Examples of suitable olefins that can be sulphurised include propyl-
ene, isobutylene, pentene, hexane, heptene, octane, nonene, decene, undecene,
dodecene, undecyl, tridecene, tetradecene, pentadecene, hexadecene, heptade-
cene, octadecene, octadecenene, nonodecene, eicosene or mixtures thereof. In
one embodiment, hexadecene, heptadecene, octadecene, octadecenene, nonode-


CA 02532964 2006-01-13
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cene, eicosene or mixtures thereof and their dimers, trimers and tetramers are
especially preferred olefins. Alternatively, the olefin can be a Diels-Alder
adduct of a diene such as 1,3-butadiene and an unsaturated ester such as butyl
(meth) acrylate.
[0086] Another class of suiphurised olefins include fatty acids and their
esters. The fatty acids are often obtained from vegetable oil or animal oil;
and
typically contain 4 to 22 carbon atoms. Examples of suitable fatty acids and
their esters include triglycerides, oleic acid, linoleic acid, palmitoleic
acid or
mixtures thereof. Often, the fatty acids are obtained from lard oil, tall oil,
peanut oil,, soybean oil, cottonseed oil, sunflower seed oil or mixtures
thereof.
In one embodiment fatty acids and mixed with olefins.
Corrosion Inhibitors
[0087] Corrosion inhibitors can include amine salts of carboxylic acids such
as octylamine octanoate, condensation products of dodecenyl succinic acid or
anhydride and a fatty acid such as oleic acid with a polyamine, e.g. a polyal-
kylene polyamine such as triethylenetetramine, and half esters of alkenyl suc-
cinic acids in which the alkenyl radical contains 8 to 24 carbon atoms with
alcohols such as polyglycols.
Antiscuffing Agents
[0088] The lubricant may also contain an antiscuffing agent. Antiscuffing
agents that decrease adhesive wear are often sulphur containing compounds.
Typically the sulphur containing compounds include organic sulphides and
polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide,
dibutyl
tetrasulphide, di-tertiary butyl polysulphide, suiphurised sperm oil,
suiphurised
methyl ester of oleic acid, suiphurised alkylphenol, sulphurised dipentene,
sulphurised terpene, sulphurised Diels-Alder adducts, alkyl sulphenyl N'N-
dialkyl dithiocarbamates, the reaction product of polyamines with polybasic
acid esters, chlorobutyl esters of 2,3-dibromopropoxyisobutyric acid, acetoxy-
methyl esters of dialkyl dithiocarbamic acid and acyloxyalkyl ethers of xantho-

genic acids and mixtures thereof.

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Extreme Pressure Agents
[0089] Extreme Pressure (EP) agents that are soluble in the oil include
sulphur and chlorosulphur-containing EP agents, chlorinated hydrocarbon EP
agents, phosphorus EP agents, and mixtures thereof. Examples of such EP
agents include chlorinated wax; organic sulphides and polysulphides such as
benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide,
sulphur-
ised sperm oil, sulphurised methyl ester of oleic acid, sulphurised
alkylphenol,
sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder ad-
ducts; phosphosulphurised hydrocarbons such as the reaction product of phos-
phorus sulphide with turpentine or methyl oleate; phosphorus esters such as
the
dihydrocarbon and trihydrocarbon phosphites, e.g., dibutyl phosphite, diheptyl
phosphite, dicyclohexyl phosphite, pentylphenyl phosphite; dipentylphenyl
phosphite, tridecyl phosphite, distearyl phosphite and polypropylene
substituted
phenol phosphite; metal thiocarbamates such as zinc dioctyldithiocarbamate and
barium heptylphenol diacid; the zinc salts of a phosphorodithioic acid; amine
salts of alkyl and dialkylphosphoric acids, including, for example, the amine
salt
of the reaction product of a dialkyldithiophosphoric acid with propylene
oxide;
and mixtures thereof.
Foam Inhibitors
[0090] Foam inhibitors are known and can include organic silicones such as
polyacetates, dimethyl silicone, polysiloxanes, polyacrylates or mixtures
thereof. Examples of foam inhibitors include poly ethyl acrylate, poly 2-
ethylhexylacrylate and poly vinyl acetate.
Demulsifiers
[0091] Demulsifiers are known and include derivatives of propylene oxide,
ethylene oxide, polyoxyalkylene alcohols, alkyl amines, amino alcohols, dia-
mines and polyamines reacted sequentially with ethylene oxide or substituted
ethylene oxides. Examples of demulsifiers include trialkyl phosphates, polyeth-

ylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-
propylene oxide) polymers.

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Pour Point Depressants
[0092] Pour point depressants are known and include esters of maleic anhy-
dride-styrene copolymers, polymethacrylates; polyacrylates; polyacrylamides;
condensation products of haloparaffin waxes and aromatic compounds; vinyl
carboxylate polymers; and terpolymers of dialkylfumarates, vinyl esters of
fatty
acids, ethylene-vinyl acetate copolymers, alkyl phenol formaldehyde condensa-
tion resins, alkyl vinyl ethers and mixtures thereof.

Friction Modifiers
[0093] Friction modifiers are known and can include fatty amines, esters,
especially glycerol esters such as glycerol monooleate, borated glycerol
esters,
fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides,
alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of
fatty
acids, sulfurized olefins, fatty imidazolines, condensation products of
carboxylic
acids and polyalkylene-polyamines, amine salts of alkyiphosphoric acids

Viscosity Modifiers
[0094] Viscosity modifiers are known and are typically polymeric materials
including styrene-butadiene rubbers, ethylene-propylene copolymers, polyisobu-
tenes, hydrogenated styrene-isoprene polymers, hydrogenated radical isoprene
polymers, polymethacrylate acid esters, polyacrylate acid esters, polyalkyl
styrenes, alkenyl aryl conjugated diene copolymers, polyolefins, polyalkyl-
methacrylates, esters of maleic anhydride-styrene copolymers and mixtures
thereof.
[0095] Some polymers can also be described as dispersant viscosity modifi-
ers (often referred to as DVM) because they also exhibit dispersant
properties.
Typically polymers of this type include polyolefins, for example, ethylene-
propylene copolymers that have been functionalized with the reaction product
of
maleic anhydride and an amine. Another type of polymer is a polymethacryla-
tee functionalised with an amine.
Seal Swelling Agents
[0096] Seal swelling agents are known and are typically esters or low viscos-
ity mineral oils with high naphthenic or aromatic content. Esters can be
derived
from monobasic and dibasic acids with monoalcohols, or esters of polyols with
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monobasic esters. Typically the alcohols contain 8 to 13 carbon atoms.
Suitable
examples of mineral oil seal swelling agents include adipates, azelates, and
sebacates. Examples of suitable mineral oil seal swell agents include Exxon
Necton-37TM (FN 1380) and Exxon Mineral Seal Oi1TM (FN 3200).
Fluidity Modifiers
[0097] Fluidity modifier are known and can include Hydrocal-38 which is a
product identified as a refined naphthenic oil, 40 Neutral naphthenic oil and
a low
molecular weight poly-a-olefin (EthylfloTM 162).
Process
[0098] The invention further provides a process for the preparation of a
composition comprising mixing:
(a) a hydrocarbyl phosphite;
(b) the condensation product of at least one fatty acid with a polyamine;
(c) a borate ester;
(d) a borated dispersant; and
(e) an oil of lubricating viscosity.
[0099] The mixing conditions are typically 15 C to 130 C, preferably 20 C
to 120 C and even more preferably 25 C to 110 C; and for a period of time in
the range 30 seconds to 48 hours, preferably 2 minutes to 24 hours, more pref-
erably 5 minutes to 16 hours and even more preferably 10 minutes to 5 hours;
and at pressures in the range 86 kPa to 266 kPa (650 mm Hg to 2000 mm Hg),
preferably 92 kPa to 200 kPa (690 mm Hg to 1500 mm Hg), and even more
preferably 95 kPa to 133 kPa (715 mm Hg to 1000 mm Hg).
[0100] The process optionally includes mixing other optional performance
additives as described above. The optional performance additives can be added
sequentially, separately or as a concentrate.
[0101] If the present invention is in the form of a concentrate the oil of
lubricating viscosity is present in an amount less than 78 wt %, preferably
less
than 65 wt%, more preferably less than 50 wt % and even more preferably less
than 45 wt % (which can be combined with additional oil to form, in whole or
in
part, a finished lubricant), the ratio of each of the above-mentioned
components,
to diluent oil is typically 80:20 to 10:90 by weight.
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Industrial Application
[0102] The compositions of the present invention are useful in a power
transmission system, specifically a mechanical power transmission and provide
a method for lubricating a transmission system, comprising supplying thereto a
lubricant comprising the composition described above. The transmission
systems are selected from group consisting of automatic transmissions, manual
transmissions, trans-axles, gears and tractor transmissions. Suitable gear
appli-
cations can include both open and closed systems.
[0103] In one embodiment the compositions of the invention are useful in
transmission fluids especially for automatic transmissions. The use of the
lubricating oil composition can impart one or more of improved wear
resistance,
anti-shudder properties, and friction durability.
[0104] The following examples provide an illustration of the invention.
These examples are non exhaustive and are not intended to limit the scope of
the
invention.
EXAMPLES
Example 1
[0105] An oil of lubricating viscosity is prepared by blending 90wt % of API
Group III, Motiva EnterpriseTM 70N oil, 3.04 mm2s-1 (cSt) at 100 C with 10 wt
% of API Group II, NesteTM 120N oil, 5.07 mm2s-1 (cSt) at 100 C. Added to the

oil are (a) 0.33 wt % of the reaction product of boric acid and
polyisobutylene
succinimide; (b) 0.15 wt % based on the total composition of, the condensation
product of a mixture of fatty acids with 16 to 18 carbon atoms with
tetraethylene
pentamine; (c) 0.2 wt % of a mixture of dialkyl C16 to C18 hydrogen
phosphites;
and (d) 0.2 wt % of the reaction product of boric acid with 1,2-
epoxyhexadecane.
To the resultant mixture, a number of other optional performance additives are
added: (a) 2.25 wt % of non-borated dispersants, (b) 2.2 wt % of antioxidants,
(c)
0.03 wt% of detergents, (d) 0.04 wt % of metal deactivators, (e) 0.3 wt % of
seal
swelling agents, (f) 55 ppm of antifoaming agents and (g) 3.1 wt % of diluent
oil.



CA 02532964 2012-02-06
Example 2
[0106] The experimental procedure is identical to the process of Example 1,
except 0.16 wt % of the reaction product of boric acid and polyisobutylene
succi-
nimide is added.
Example 3
[0107] The experimental procedure is identical to the process of Example 1,
except that 8.8 wt % of a dispersant viscosity modifier, 0.02 wt % of a pour
point
depressant and 0.11 wt % of dibutyl hydrogen phosphite are added.
Example 4
[01081 The experimental procedure is identical to the process of Example 2,
except 0.4 wt % of tributyl borate is added.
Test 1: Ford/Greening Low Speed Friction Test
[01091 Approximately 300 ml of sample is placed in a modified SAE Number 2
machine with a variable speed drive system and the sample is rotated at about
300
rpm for about 30 minutes. For a more detailed description of the test refer to
Ford
Motor Company MERCON V specification for Automatic Transmission Fluid,
January 1 1999. The recommended maximum wear in this test is 0.076mm. The
results obtained are:

Example Ford/Greening Low Speed Friction Test (mm)
1 0.022
2 0.023
3 0.025
4 0.020
Test 2: Timken Wear Test
[01101 This procedure is used to determine the anti-wear properties of
automatic
transmission fluids by means of the TimkenTM Lubricant Tester fitted with a
sample
holder and filled with about 180 ml of test fluid and operated at 800 rpm with
a
4.08 kg (9.0 lb) load at 150 C. A FalexTM test ring is attached to the
rotating shaft
of the TimkenTM machine. A rectangular test block is held securely within the
small-sample adapter and fully immersed in the test lubricant and then brought
into
contact with the rotating ring. The results obtained are:

26


CA 02532964 2012-02-06

Example Timken Wear Test (mm)
1 0.55
2 0.63
3 0.60
4 0.57
Test 3: Ford Clutch Friction Durability Test
[01111 Approximately 300 ml of sample is placed in a modified SAE Number 2
machine equipped with SD-1777 friction material clutch plate and C8AP-7B442-A
separator plate material. The clutch plate and separator plate are engaged and
then

disengaged 20,000 times. For a more detailed description of the test refer to
Ford
Motor Company MERCON V specification for Automatic Transmission Fluid,
January 1 1999. The recommended maximum wear in this test is 0.076mm. The
results obtained are:
Example Ford Clutch Friction Durability Test (mm)
1 0.053
2 0.09
3 0.06
4 0.073
[01121 The analysis shows the compositions of the invention produce good
results for the various automatic transmission fluid tests. Example 2 in test
3 gives
a somewhat high value; it is believed that this value can be significantly
reduced by
increasing the amount of the borated dispersant.
[01131 Except in the Examples, or where otherwise explicitly indicated, all
numerical quantities in this description specifying amounts of materials,
reaction
conditions, molecular weights, number of carbon atoms, and the like, are to be
understood as modified by the word "about." Unless otherwise indicated, each
chemical or composition referred to herein should be interpreted as being a
com-
mercial grade material which may contain the isomers, by-products,
derivatives,
and other such materials which are normally understood to be present in
27


CA 02532964 2006-01-13
WO 2005/010134 PCT/US2004/020856
the commercial grade. However, the amount of each chemical component is
presented exclusive of any solvent or diluent oil, which may be customarily
present in the commercial material, unless otherwise indicated. It is to be
understood that the upper and lower amount, range, and ratio limits set forth
herein may be independently combined. Similarly, the ranges and amounts for
each element of the invention can be used together with ranges or amounts for
any of the other elements. As used herein, the expression "consisting
essentially
of" permits the inclusion of substances that do not materially affect the
basic
and novel characteristics of the composition under consideration.
28

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date 2012-09-18
(86) PCT Filing Date 2004-06-29
(87) PCT Publication Date 2005-02-03
(85) National Entry 2006-01-13
Examination Requested 2009-06-26
(45) Issued 2012-09-18

Abandonment History

There is no abandonment history.

Maintenance Fee

Last Payment of $458.08 was received on 2022-06-24


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Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $400.00 2006-01-13
Registration of a document - section 124 $100.00 2006-04-06
Maintenance Fee - Application - New Act 2 2006-06-29 $100.00 2006-06-01
Maintenance Fee - Application - New Act 3 2007-06-29 $100.00 2007-05-31
Maintenance Fee - Application - New Act 4 2008-06-30 $100.00 2008-06-03
Maintenance Fee - Application - New Act 5 2009-06-29 $200.00 2009-06-02
Request for Examination $800.00 2009-06-26
Maintenance Fee - Application - New Act 6 2010-06-29 $200.00 2010-06-02
Maintenance Fee - Application - New Act 7 2011-06-29 $200.00 2011-06-03
Maintenance Fee - Application - New Act 8 2012-06-29 $200.00 2012-06-08
Final Fee $300.00 2012-07-03
Maintenance Fee - Patent - New Act 9 2013-07-02 $200.00 2013-05-30
Maintenance Fee - Patent - New Act 10 2014-06-30 $250.00 2014-06-23
Maintenance Fee - Patent - New Act 11 2015-06-29 $250.00 2015-06-22
Maintenance Fee - Patent - New Act 12 2016-06-29 $250.00 2016-06-27
Maintenance Fee - Patent - New Act 13 2017-06-29 $250.00 2017-06-26
Maintenance Fee - Patent - New Act 14 2018-06-29 $250.00 2018-06-25
Maintenance Fee - Patent - New Act 15 2019-07-02 $450.00 2019-06-21
Maintenance Fee - Patent - New Act 16 2020-06-29 $450.00 2020-06-19
Maintenance Fee - Patent - New Act 17 2021-06-29 $459.00 2021-06-25
Maintenance Fee - Patent - New Act 18 2022-06-29 $458.08 2022-06-24
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
THE LUBRIZOL CORPORATION
Past Owners on Record
SMOGGIE, JOHN C.
SUMIEJSKI, JAMES L.
TIPTON, CRAIG
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 2006-01-13 1 54
Claims 2006-01-13 3 84
Description 2006-01-13 28 1,321
Cover Page 2006-03-14 1 33
Claims 2006-01-14 3 131
Claims 2012-02-06 3 76
Abstract 2012-02-06 1 13
Description 2012-02-06 28 1,335
Abstract 2012-03-05 1 13
Cover Page 2012-08-23 1 36
Assignment 2006-01-13 3 86
PCT 2006-01-13 3 101
Fees 2009-06-02 1 37
Prosecution-Amendment 2011-08-08 3 134
Correspondence 2006-03-09 1 29
Assignment 2006-04-06 2 67
Fees 2006-06-01 1 30
PCT 2006-01-14 8 328
Fees 2007-05-31 1 30
Fees 2008-06-03 1 37
Prosecution-Amendment 2009-06-26 1 34
Fees 2010-06-02 1 38
Prosecution-Amendment 2012-02-06 17 636
Correspondence 2012-03-05 1 32
Correspondence 2012-07-03 1 54