ENGINE OIL CONTAINING PHENOL ALKOXYLATES

HUILE A MOTEUR CONTENANT DES ALKOXYLATES DE PHENOL

English Abstract

Engine oils containing up to 10% w/w of a base oil component comprising a
reaction product of an alkylphenol or bisphenol A with butylene oxide or
butylene oxide/propylene oxide. These engine oils show improved
high-temperature stability and improved piston cleaning properties.

Claims

WHAT IS CLAIMED IS:
1. An engine oil consisting of base oil components and
additives and containing, as base oil component, from 1 to 10%
w/w of an alkylphenol alkoxylate of the formula:
R1-[O-(R2-O)nH]m
in which
R1 is an alkylphenol radical having up to 2 alkyl radicals
of from 6 to 24 carbon atoms or is a bisphenol radical,
R2 is a radical of butylene oxide or butylene oxide/
propylene oxide,
n is an integer from 10 to 100 and
m is 1 or 2.
2. An engine oil as claimed in claim 1, wherein R2 0 is
derived from butylene oxide.
3. An engine oil as claimed in claim 1, wherein R2 0 is
derived from a mixture of propylene oxide and butylene oxide
containing not more than 80% molar of propylene oxide.
4. A motor oil as claimed in any one of claims 1 to 3, and
containing, as further base oil components, mineral oil,
poly-.alpha.-olefins, poly-internal-olefins, hydrocracked oil,
dicarboxylates and neopolyol esters.
5. An engine oil as claimed in any one of claims 1 to 4,
wherein R1 is the radical of a mono- or di-alkyiphenol having
from 6 to 24 carbon atoms in the alkyl moiety.
6. An engine oil as claimed in any one of claims 1 to 4,
wherein R1 is a bisphenol A radical.

Description

~ 20 34 t44 ~
ENGINE OIL CONTAINING PHENOL ALKOXYLATES
The present invention relates to an engine oil having a
content of phenol-started oil-soluble polyethers for improving
piston cleanliness in automobile engines.
Modern lubricants (engine oils) must satisfy increasing
demands to promote wear reduction, longer running times,
10 reduction of deposits, engine cleanliness and improved low-
temperature properties. Since only a limited amount of
additives may be used and the amount of detergents used in
internal combustion engine oils may not exceed a specific
value, and since the use of wear protectants (zinc
dithiophosphates) is restricted because of the three-way
catalytic converters and the presence of too much dirt
dispersant can cause attack on the rubber seals, attempts are
being made to improve the performance of engine oils by the
use of novel base oils. It is thus an object of the present
20 invention to provide novel engine oil components which improve
performance significantly over the prior art.
This object is achieved by an engine oil containing, as base
oil component, from 1 to 10% w/w of an alkylphenol alkoxylate
of the formula:
R1-[O-(R2-O)nH]m
in which
30 R1 is an alkylphenol radical having up to 2 alkyl radicals
of from 6 to 24 carbon atoms or is a bisphenol radical,
R2 is a radical of butylene oxide or butylene oxide/
propylene oxide,
n is an integer from 10 to 100 and
m is 1 or 2.

la ~ 1 4 4 ~4
In a preferred embodiment of the invention those compounds of
the above formula are used in which R2O is derived from a
mixture of butylene oxide and propylene oxide containing not
more than 80% of propylene oxide or, preferably, from butylene
oxide alone.
The phenol component is alkylated with 1 or 2 alkyl radicals
having from 6 to 24, preferably 9 to 12, carbon atoms or
comprises a bisphenol.
The reaction of the phenol with butylene oxide or with a
mixture of butylene oxide and propylene oxide or with butylene
oxide followed by propylene oxide or vice versa is effected
.

EIASF Akti~n~ llcchaft 2 O.Z.005~/41346
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100, preferably from 10 to 50, moles of alkylene oxide are reacted per OH
group of the phenol.
We particularly prefer to react from 5 to 25 moles of butylene oxide alone
5 per phenol group.
Specific examples of suitable alkylphenols are dodecylphenol, nonylphenol
and bisphenol A.
The preparation of the polyethers is described below in detail.
Preparation Example (in general)
Reaction of alkylphenol or bisphenol A with alkylene oxide(s)
In a stirred autoclave, finely pulverized KOH is stirred into the alkylphe-
nol and heated to 130~C under a pressure of 200 mbar, the amount of KOH be-
ing 0.lZ w/w of the total mixture. This procedure removes residual traces
of water. The autoclave is then sealed, and alkylene oxide is pumped in so
20 as to set up a pressure of not more than 6 bar. Different alkylene oxides
may be introduced concurrently or consecutively so as to form random
polyethers or blocks having more or less distinct transitions. Following
the feeds of alkylene oxides, the pressure drops to 2 to 3 bar over a pe-
riod of from 3 to 10 hours. ~hen this pressure has been reached, the tem-
2s perature is reduced to 80~C and the autoclave is depressurized via a di-
aphragm valve and evacuated to 20 to 30 mbar. After this reduced pressure
has been maintained for about 1 hour, equivalent amounts of acid ion ex-
changers are added to remove potassium and the mixture is filtered.
30 The following products were prepared using the above method:
A: Isononylphenol is reacted with l-butene oxide in a molar ratio of
1:24. The resulting polyether has a viscosity of 320 mm2/s at 40~C and
a calculated molecular weight of 1848.
B: Isononylphenol is reacted with l-butene oxide in a molar ratio of 1:8.
The resulting polyether has a viscosity of 130 mm2/s at 40~C and a
calculated molecular weight of 796.
C: Isononylphenol is reacted with l-butene oxide and propene oxide in a
molar ratio of 1:12:12. The resulting polyether has a viscosity of 125
mm2/s at 40~C and a calculated molecular weight of 1684.
3 )

BASE Alctia"R~5~ ft 3 O. Z 0050/41346
203414~
D: Nonylphenol is reacted with Propene oxide in a molar ratio of 1:10.
The resulting polyether has a viscosity of 87 mmZ~s at 40~C and a
molecular weight of 806.
E: Bisphenol A is reacted with butene oxide in a molar ratio of 1:10. The
resulting polyether has a viscosity of 360 mm2/s at 40~C and a
molecular weight of 878.
F: Bisphenol A is reacted with butene oxide in a molar ratio of 1:15. The
o resulting polyether has a viscosity of 320 mm2/s at 40~C and a
molecular weight of 1238.
G: Bisphenol A is reacted with butene oxide in a molar ratio of 1:25. The
resulting polyether has a viscosity of 380 mm2/s at 40~C and a
molecular weight of 1958.
Engine oils are liquids based on selected base oils to which additives(active substances) are added in order to achieve special effects within
the engine, for example to keep the engine clean, to reduce deposits, to
20 improve high-temperature resistance, to reduce wear and to make longer
running times possible (cf. dlfibel Aral, 10th Edition 1989.1, pp. 23-30,
and 1989.2, pp. 4-9).
The alkylphenoxylates to be used in accordance with the present invention
25 are added to engine oils, particularly those based on hydrocarbons, in
amounts of up to 10% and in particular amounts ranging from 1 to 8%, by
weight.
A representative engine oil mixture contains, for example, the following
30 essential components:
from 80 to 95~O w/w of base oil components,
from 0.5 to 2.5% w/w of viscosity index improvers (1007, strength),
from 1.5 to 10% w/w of ashless dispersants,
35 from 1.5 to 8% w/w of detergents,
from 20.5 to 6% w/w of wear protectants,
from 1 to 8% w/w of phenoxylates added in accordance with the invention.
The alkylphenoxylates to be used according to the invention show distinctly
greater stability at high temperatures than conventional alkoxylates (DTG).

BASF Aktien8esellscha~t 4 O. Z. 0050/41346 2~3~1 4~
The good high-temperature stability and very good lubricating characteris-
tics of the alkylphenoxylates to be used in the present invention are par-
ticularly apparent in tests carried out on the driving mechanism of
automobile engines. The tests were based on a high-quality engine oil API
sSF/CD, to which 5% of alkylphenoxylate was added in each test. Engine pre-
qualification tests were carried out by the method of testing piston clean-
liness laid down in the MWM Diesel Engine Test, Part B, DIN 51,361, CEC-L-
12-A-76. It was found, surprisingly, that the engine oils containing 5% of
the alkylphenoxylates proposed by the invention with their ratings of up to
1O79 points (i.e. very good ratings) were clearly superior to the control
(engine oil API SF/CD) with its ratings of 67 and 69, as shown in the Table
below.
Alkoxylates started, for example, with tridecanol and containing 1-butene
15 oxide as alkylene oxide produced no improvement on the engine test results.
Table
MW~-B diesel engine tests on the piston cleaning properties of engine oil
20 blends containing 5% w/w of an alkylphenoxylate proposed by the present in-
vention
25 No. Engine Oil Formulation MWM-B Rating
1 Engine oil A (API SF/CD) 67 and 69
2 Engine oil A + 5% w/w of A 76 and 79
30 3 Engine oil A + 5X w/w of B (Co~p. Example) 66
4 Engine oil A + 5X w/w of C 74
35 5 Engine oil A + 5X w/w of D (Comp. Example) 66
6 Engine oil A + 5% w/w of E 75
7 Engine oil A + 5X w/w of F 72
~o8 Engine oil A + 5% w/w of G 72
M~M-B ratings:
65 76 excellent,
71-75 very good,
66-70 good,
61-65 satisfactory,
50-60 fair.