Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
1999-11-19
2001-10-30
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C427S216000, C427S220000
Reexamination Certificate
active
06310230
ABSTRACT:
TECHNICAL FILED
The present invention relates to N-substituted-&ohgr;-(alkoxysilyl)alkylamines and salts thereof, and to a process for production thereof.
BACKGROUND ART
Certain silane compounds, including some amine-containing silane compounds, are said to be useful for attaching organic groups to mineral fillers; see “Silane treatment of mineral fillers—practical aspects”, by E. J. Sadler, Plastics, Rubber and Composites Processing and Applications Vol. 24, No. 5, 1995, pages 271 to 275.
It is known to prepare some N-substituted-3-(trialkoxysilyl)propylamines by reacting a 3-chloropropyltrialkoxysilane with a primary amine or reacting an alkyl chloride with a 3-aminopropyltrialkoxysilane, at reflux in an alcoholic solution, where the alcohol solvent corresponds to the alkyl group of the alkoxy portion of the silane. This is largely unsatisfactory as the alcohols CH
3
OH, C
2
H
5
OH and C
3
H
7
OH boil at temperatures below 98° C., which is lower than the temperature required to obtain good yields of the desired products in a reasonable time. While higher boiling alcohols, for example butanol, may be used to achieve higher reflux temperatures and hence increased reaction rates, this can result in an exchange of alkoxy groups of the alcohol with those of the silane and a much decreased yield of the desired producl The reaction rates can be increased by using higher temperatures and a pressure autoclave, but this still requires removal of the solvent alcohol, which complicates the synthesis, and also requires specialized equipment (autoclave), which is undesirable.
It is also known to prepare some N-substituted-3(trialkoxysilyl)propylamines by reacting 3-bromopropyltrialkoxysilane with a primary amine, or reacting an alkyl bromide with a 3-aminopropyltrialkoxysilane at reflux in alcohol solution. Again, it is desirable that the alkoxy group of the alcohol is the same as the alkoxy group of the silane. While in some cases satisfactory yields can be obtained, in others the temperature of the boiling solvent is too high, causing unwanted side reactions, for instance dehydrobromination of the starting 3-bromopropyltrialkoxysilane. In any case, it is necessary to remove the alcohol to obtain the required product, which is expensive and disadvantageous, particularly if it is important to remove all traces of the solvents.
SUMMARY OF THE INVENTION
It is an object of the present invention to obviate or mitigate at least one of the above-identified disadvantages of the prior art.
It is another object of the present invention to provide novel N-substituted-&ohgr;-(alkoxysilyl)alkylamines and salts thereof.
It is yet another object of the present invention to provide a novel process for producing N-substituted-&ohgr;-(alkoxysilyl)alkylamines and salts thereof.
Accordingly, in one of its aspects, the present invention provides a process for producing a compound of Formula I:
wherein
R
1
is a C
6
-C
40
alkyl or alkenyl group that is straight-chained or branched, a C
6
-C
40
aryl group, a C
7
-C
40
aralkyl group or a group R
5
A(CH
2
)
p
wherein R
5
is a C
6
-C
30
alkyl or alkenyl group that is straight-chained or branched, p is an integer from 2 to 6 and A is O or NH;
R
2
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group) or a C
3
-C
12
alkenyl group (preferably a C
3
-C
5
alkenyl group);
R
3
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group), a C
1
-C
12
alkoxy group (preferably a C
1
-C
5
alkoxy group), a C
2
-C
12
alkenyl group (preferably a C
2
-C
5
alkenyl group) or a C
3
-C
12
alkenyloxy group (preferably a C
3
-C
5
alkenyloxy group);
R
4
has the same definition as R
3
and may be the same as R
4
or different;
R
5
is a divalent alkylene group having up to 10 carbon atoms and is optionally interrupted one, two or three times by a phenylene group; and
X is an anion;
the process comprising the step of:
(a) reacting a compound of the Formula II:
R
1
—NH
2
(II)
wherein R
1
is as defined above, with a compound of Formula III:
wherein R
2
, R
3
, R
4
, R
6
and X are as defined above, in the absence of a solvent; or
(b) reacting a compound of the Formula IV:
R
1
—X (IV)
wherein R
1
and X are as defined above, with a compound of Formula V:
wherein R
2
, R
3
, R
4
and R
6
are as defined above, in the absence of a solvent.
It is surprising that the N-substituted-&ohgr;-(alkoxysilyl)alkylamines of Formula I can be obtained in good yields, within reasonable reaction times, without contamination by alcoholic solvent and without necessity for removal of alcoholic solvent.
In another of its aspects, the present invention provides a compound of Formula I:
wherein
R
1
is a C
12
-C
40
alkyl or alkenyl group that is straight-chained or branched, a C
6
-C
40
aryl group, a C
7
-C
40
aralkyl group or a group R
5
A(CH
2
)
p
wherein R
5
is a C
6
-C
30
alkyl or alkenyl group that is straight-chained or branched, p is an integer from 2 to 6 and A is O or NH;
R
2
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group) or a C
3
-C
12
alkenyl group (preferably a C
3
-C
5
alkenyl group);
R
3
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group), a C
1
-C
12
alkoxy group (preferably a C
1
-C
5
alkoxy group), a C
2
-C
12
alkenyl group (preferably a C
2
-C
5
alkenyl group) or a C
3
-C
12
alkenyloxy group (preferably a C
3
-C
5
alkenyloxy group);
R
4
has the same definition as R
3
and may be the same as R
4
or different;
R
6
is a divalent alkylene group having up to 10 carbon atoms and is optionally interrupted one, two or three times by a phenylene group; and
X is an anion.
In another of its aspects, the present invention provides a compound of Formula:
wherein
R
1
is a C
12
-C
40
alkyl or alkenyl group that is straight-chained or branched, a C
6
-C
40
aryl group, a C
7
-C
40
aralkyl group or a group R
5
A(CH
2
)
p
wherein R
5
is a C
6
-C
30
alkyl or alkenyl group that is straight-chained or branched, p is an integer from 2 to 6 and A is O or NH;
R
2
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group) or a C
3
-C
12
alkenyl group (preferably a C
3
-C
5
alkenyl group);
R
3
is a C
1
-C
12
alkyl group (preferably a C
1
-C
5
alkyl group), a C
1
-C
12
alkoxy group (preferably a C
1
-C
5
alkoxy group), a C
2
-C
12
alkenyl group (preferably a C
2
-C
5
alkenyl group) or a C
3
-C
12
alkenyloxy group (preferably a C
3
-C
5
alkenyloxy group);
R
4
has the same definition as R
3
and may be the same as R
4
or different; and
R
6
is a divalent alkylene group having up to 10 carbon atoms and is optionally interrupted one, two or three times by a phenylene group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The anion X is suitably a chloride, bromide or iodide anion, of which the chloride and the bromide are preferred. The preferred reaction conditions vary, depending upon whether X is chlorine or bromine. If X is chlorine, it is preferred to carry out the reaction at a temperature at least about 100° C., more preferably in the range of from about 130° C. to about 185° C. The reaction may take anywhere from about 30 minutes to about 4 hours. If X is bromine, then it is preferred to operate at a lower temperature, preferably from about 30° C. to about 75° C. With bromine the reaction proceeds more slowly and reaction times of from about 8 to 24 hours are not unusual.
In one embodiment of the present process, an amine compound of Formula II is reacted with an alkoxysilane compound of Formula Ill.
Non-limiting examples of suitable amines of Formula II may be selected from the group comprising hexylamine, octylamine, nonylamine, decylamine, octadecylamine, octadec-enylamine and mixtures thereof. Indeed, mixed amines are commercially available and these are conveniently suitable for use. Nonimited examples of such amines may be selected from the group comprising soya amine, tall oil amine, stearyl amine, tallow amine, dihydrogenated tallow amine, cocoamine, rosin amine, palmitylamine and mixtures thereof. These amines may be use in distilled or undistilled form. When R
1
is alkenyl, it m
Bayer Inc.
Cheung Noland J.
Gil Joseph C.
Shaver Paul F.
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