Solid anti-friction devices – materials therefor – lubricant or se – Lubricants or separants for moving solid surfaces and... – Organic nitrogen compound
Reexamination Certificate
2001-10-11
2003-04-15
Howard, Jacqueline V. (Department: 1764)
Solid anti-friction devices, materials therefor, lubricant or se
Lubricants or separants for moving solid surfaces and...
Organic nitrogen compound
C044S434000, C508S562000
Reexamination Certificate
active
06548461
ABSTRACT:
The present invention relates to special polyalkene alcohol polyetheramines, their use as carrier oils, detergents or dispersants in fuel and lubricant compositions and fuel and lubricant additive concentrates and fuel and lubricant compositions themselves which contain these polyalkene alcohol polyetheramines.
Carburetors and intake systems of gasoline engines as well as injection systems for fuel metering are increasingly contaminated by impurities which are caused by dust particles from the air, uncombusted hydrocarbon residues from the combustion chamber and the crank case vent gases passed into the carburetor.
These residues shift the air/fuel ratio during idling and in the lower part-load range so that the mixture becomes leaner and the combustion more incomplete and in turn the proportions of uncombusted or partially combusted hydrocarbons in the exhaust gas become greater and the gasoline consumption increases.
It is known that, to avoid these disadvantages, fuel additives are used for keeping valves and carburetors or injection systems of gasoline engines clean (cf. for example: M. Rossenbeck in Katalysatoren, Tenside, Mineralöladditive, Editors J. Falbe and U. Hasserodt, page 223, G. Thieme Verlag, Stuttgart 1978).
Frequently used fuel additives of this type are polyisobuteneamines, as described, for example, in EP-A 244 616, or polyetheramines, as described, for example, in EP-A 310 875.
The class consisting of the polyisobuteneamines generally has a good effect but—depending on the chain length of a poly(iso)butene moiety in the molecule, the engine type and the additive concentration used—they often cause sticking of the valves, which may lead to total failure of the engine. The sticking of the valve is understood here as meaning complete loss of compression in one or more cylinders of the internal combustion engine if—owing to polymer deposits on the valve shaft—spring forces are no longer sufficient to close the valves properly.
Although polyetheramines generally also exhibit good activity, their usability is subject to certain restrictions. Owing to the polar polyether chain, the solubility in the nonpolar fuel may be reduced. For compensation, it is then necessary either to use long-chain alkanols as initiator molecules for the preparation of the polyetheramines, which are industrially available only to a limited extent, or it is necessary to use long-chain epoxides such as butylene oxides, pentene oxides or cyclohexene oxide, to synthesize the polyether chain, which entails substantially higher costs.
It is an object of the present invention to provide mineral oil additives, in particular detergents, for lubricant compositions and in particular fuel compositions, which no longer have the prior art problems described.
We have found that this object is achieved by polyetheralkene alcohol polyetheramines of the formula I
R
1
—(CH
2
)
n
—(O—A)
m
—NR
2
R
3
(I)
where
R
1
is a polyalkene radical derived from C
2
- to C
30
-alkenes and having a number average molecular weight of from 300 to 5000,
R
2
and R
3
may be identical or different and are hydrogen, aliphatic or aromatic hydrocarbon radicals, primary or secondary, aromatic or aliphatic aminoalkylene radicals or polyaminoalkylene radicals, polyoxyalkylene radicals, heteroaryl or heterocyclyl radicals or, together with the nitrogen atom to which they are bonded, form a ring in which further heteroatoms may be present, the maximum number of carbon atoms in R
2
and R
3
together being 400,
A is an alkylene group of 2 to 8 carbon atoms,
m is from 1 to 200 and
n is 0 or 1.
Suitable radicals R
1
are straight-chain or branched hydrocarbon groups which are derived from C
2
- to C
30
-alkenes, in particular from C
3
- to C
12
-alkenes, especially from C
3
- to C
6
-alkenes. Typical alkenes are ethene, propene, butenes, pentenes, hexenes, heptenes, octenes, nonenes, decenes, undecenes and dodecenes. Of particular interest are propene, n-butene and isobutene. The polyalkene on which the hydrocarbon radical R
1
is based is obtainable by oligomerization or polymerization of these alkenes, the oligomerization or polymerization being carried out as a rule (for example by cationic or coordination oligomerization or polymerization) so that the chain termination leads to a double bond which can be further functionalized to give the corresponding polyalkene alcohol.
R
1
is preferably a polybutyl or polyisobutyl radical derived from isobutene and up to 20% by weight of n-butene and having a number average molecular weight (M
N
) of from 300 to 2500. R
1
is particularly preferably a polybutyl or polyisobutyl radical having a number average molecular weight of from 350 to 1500, in particular from 400 to 850, especially from 450 to 700. Preferably, R
1
is also composed of isobutene units alone.
R
1
may preferably be based on highly reactive polyisobutene (having double bonds permanently in the &agr;-position) which—as described in EP-A 277 345—can be converted into the corresponding alcohol R
1
—CH
2
—OH (n=1) by hydroformylation. Where n=0, polybutenes or polyisobutenes having double bonds which are predominantly further toward the interior of the polymer chain (for example in the &bgr;- and &ggr;-position) are usually used as starting materials in the preparation of corresponding polybutene alcohols or polyisobutene alcohols; these are then usually converted into the poly(iso)butene alcohols either by ozonolysis and subsequent reduction or by epoxidation and subsequent reduction or by hydroboration and subsequent hydrolysis or by halogenation with chlorine or bromine and subsequent alkaline hydrolysis.
The maximum number of carbon atoms in R
2
and R
3
together is preferably 200, in particular 100, especially 30. When nitrogen atoms are present in R
2
and R
3
, their maximum number together is preferably 20, in particular 10, especially 5. When oxygen atoms are present in R
2
and R
3
, their maximum number together is 60, in particular 20, especially 10.
In a preferred embodiment, R
2
and R
3
are identical or different and are each hydrogen, alkyl, aryl, hydroxyalkyl, an aminoalkylene radical of the formula III
—R
4
—NR
5
R
6
(III)
where R
4
is an alkylene radical and R
5
and R
6
, which are identical or different, are each hydrogen, alkyl, aryl, hydroxyalkyl or a polybutene or polyisobutene radical, a polyaminoalkyl radical of the formula IV
[—R
4
—NR
5
]
p
R
6
(IV)
where the radicals R
4
and the radicals R
5
are each identical or different, R
4
, R
5
and R
6
have the abovementioned meanings and p is from 2 to 8, or a polyoxyalkylene radical of the formula V
[—R
4
—O]
q
—X (V)
where the radicals R
4
are identical or different and have the above meanings, X is alkyl or H and q is from 1 to 30, or R
2
and R
3
, together with the nitrogen atom to which they are bonded, form a morpholinyl, pyridyl, piperidyl, pyrrolyl, pyrimidinyl, pyrrolinyl, pyrrolidinyl, pyrazinyl or pyridazinyl radical.
In a particularly preferred embodiment, R
2
and R
3
are identical or different and are each hydrogen, C
1
-C
10
-alkyl, phenyl, naphthyl, C
1
-C
10
-hydroxyalkyl, an aminoalkylene radical of the formula III
—R
4
—NR
5
R
6
(III)
where R
4
is a C
2
-C
10
-alkylene radical and R
5
and R
6
, which are identical or different, are each hydrogen, C
1
-C
10
-alkyl, phenyl, naphthyl, C
1
-C
10
-hydroxyalkyl or a polybutene or polyisobutene radical, each of 20 to 398, especially 30 to 180, carbon atoms, a polyaminoalkylene radical of the formula IV
[—R
4
—NR
5
]
p
R
6
(IV)
where the radicals R
4
and the radicals R
5
are each identical or different, R
4
, R
5
and R
6
have the abovementioned meanings and p is from 2 to 8, or a polyoxyalkylene radical of the formula VI
[—R
4
—O]
q
—H (VI)
where the radicals R
4
are identical or different and have the above meanings and q is from 1 to 30 or R
2
and R
3
, together with the nitrogen atom to which they are bonded, form a morpholinyl radical.
I
Günther Wolfgang
Massonne Klemens
Oppenländer Knut
Posselt Dietmar
Rath Hans Peter
Basf Aktiengesellschaft
Howard Jacqueline V.
Keil & Weinkauf
LandOfFree
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