Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2001-06-11
2001-12-04
Shaver, Paul F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C549S215000
Reexamination Certificate
active
06326506
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to the selective production of specific organosilicon compounds which are useful as silane coupling agents, as starting materials for various silicon compounds, are useful as various additives, and as starting materials for various organosilicon polymers.
BACKGROUND OF THE INVENTION
Hydrosilylation involving the use of platinum catalysts is a particularly important technique in the silicone industry, particularly in the production of organic modified silicones and silane coupling agents. Many attempts have been made in the past to improve the selectivity for the product structure or the hydrosilylation reaction rate in this process.
The following are examples of improvements in hydrosilylation reaction rates.
U.S. Pat. No. 5,359,111 describes a process where the hydrosilylation reaction is carried out in an oxygen gas atmosphere.
U.S. Pat. No. 5,449,802 describes a process where the hydrosilylation reaction is carried out in the presence of acetylene alcohol or a derivative thereof.
U.S. Pat. No. 5,481,016 describes a process where the hydrosilylation reaction is carried out in the presence of an alcohol having a tertiary structure or a derivative thereof.
U.S. Pat. No. 5,486,637 describes a process where the hydrosilylation reaction is carried out in the presence of alcohol having an unsaturated structure and a branched structure (tertiary or secondary) or a derivative thereof.
Chem. Eur. J.
1998, 4. No. 10, p. 2008-2017 describes a process where the hydrosilylation reaction is carried out in the presence of a naphthyl ketone.
Japanese Unexamined Patent Application (Kokai) 11-80167 describes a process where the hydrosilylation reaction is carried out in the presence of a sulfur compound.
Methods for bringing about a hydrosilylation reaction in the presence of a platinum catalyst and various additives have been proposed in order to improve the selectivity for certain products during hydrosilylation. The following are examples of reactions for the hydrosilylation of allyl chlorides with hydrochlorosilanes in the presence of a platinum catalyst. Japanese Unexamined Patent Application (Kokai) 9-157276 and Japanese Unexamined Patent Application (Kokai) 55-145693: phosphines are used as additives. Japanese Unexamined Patent Application (Kokai) 9-192494: tertiary amines with alkyl or aralkyl groups as substituents are used as additives. Japanese Unexamined Patent Application (Kokai) 10-72474: amino alcohol derivatives are used as additives.
U.S. Pat. No. 5,563,287 and U.S. Pat. No. 5,567,848 disclose methods featuring the use of cycloalkadiene compounds in the hydrosilylation of alkyne-based hydrocarbons.
Although the prior art discloses methods for improving the yield of the target product in specific systems, no method widely applicable to hydrosilylation reactions has yet been established for satisfactorily increasing the proportion of the target product over the proportion of by-products.
An object of the present invention is to allow target products (&bgr;-hydrosilylated products) having a structure in which silicon atoms are bonded to the terminal carbon atoms of unsaturated groups, which are the reactive groups of unsaturated compounds, to be produced more efficiently than in the past compared to by-products (substituted reaction products produced in the case of allyl chlorides and the like, or &agr;-hydrosilylated products produced in the case of styrenes and the like) during hydrosilylation reactions in which the aforementioned unsaturated compounds having terminal unsaturated groups and silicon compounds having hydrogen atoms directly bonded to silicon atoms are allowed to react in the presence of a platinum catalyst.
SUMMARY OF THE INVENTION
A method of preparing an organosilicon compound comprising effecting a hydrosilylation reaction between (a) unsaturated compounds with terminal unsaturated groups and (b) silane compounds described by formula HSiR
0
m
W
3−m
, where W is a C
1
to C
6
alkoxy group, C
6
to C
10
aryloxy group, and halogen atoms, R
0
is an organic group, and m is 0, 1, or 2 in the presence of (c) a platinum catalyst and (d) an auxiliary catalyst selected from the group consisting of (1) silyl esters of acids derived from oxo acids of sulfur; (2) amide compounds having N—Si bonds; (3) urea compounds; (4) silyl esters of carbamic acid; (5) phosphoric acid compounds; and (6) cyclic compounds selected from the group consisting of (i) hydroxypyridine compounds, (ii) 8-hydroxyquinoline compounds, (iii) oxazolidinone compounds, and (iv) N-hydroxysuccinimide compounds.
DESCRIPTION OF THE INVENTION
The present invention is a method of preparing an organosilicon compound comprising effecting a hydrosilylation reaction between (a) unsaturated compounds with terminal unsaturated groups and (b) silane compounds described by formula HSiR
0
m
W
3−m
, where W is a C
1
to C
6
alkoxy group, C
6
to C
10
aryloxy group, and halogen atoms, R
0
is an organic group, and m is 0, 1, or 2 in the presence of (c) a platinum catalyst and (d) an auxiliary catalyst selected from the group consisting of
(1) silyl esters of acids derived from oxo acids of sulfur; (2) amide compounds having N—Si bonds; (3) urea compounds; (4) silyl esters of carbamic acid; (5) phosphoric acid compounds; and (6) cyclic compounds described by the following formulas selected from the group consisting of (i) hydroxypyridine compounds, (ii) 8-hydroxyquinoline compounds, (iii) oxazolidinone compounds, and (iv) N-hydroxysuccinimide compounds:
where R
9
, R
10
, R
11
, R
12
, R
13
, and R
14
are each independently selected from the group consisting of hydrogen atoms, halogen atoms, C
1
to C
10
alkyl groups, C
6
to C
10
aryl groups, C
1
to C
10
alkoxy groups, and groups described by R
2
3
Si—, where each R
2
is independently selected from the group consisting of C
1
to C
10
hydrocarbon groups, C
1
to C
10
alkoxy groups, chlorine atoms, and hydrogen atoms with a maximum of 2 hydrogen atoms present; and X is a hydrogen atom or a group described by R
2
3
Si—, where R
2
is the same as described above.
The aforementioned objectives are successfully achieved in the present invention by ensuring the presence of certain compounds during the aforementioned hydrosilylation reaction. The aforementioned certain compounds in the present invention are used as auxiliary catalysts during hydrosilylation reactions. Specifically, compounds are selected from among (d)(1) through (d)(6). Herein the compounds (d) are sometimes referred to as “substances acting as auxiliary catalysts” or “auxiliary catalyst”. These auxiliary catalyst allow the target product to be produced preferentially over the aforementioned by-products in hydrosilylation reactions of (a) unsaturated compounds with terminal unsaturated groups in the range described below and (b) silane compounds represented by HSiR
0
m
W
3−m
, where each W is selected from the group consisting of C
1
to C
6
alkoxy groups, C
6
to C
10
aryloxy groups, and halogen atoms selected from F, Cl, Br, and I, R
0
is an organic group, and m is 0, 1, or 2, in the presence of (c) a platinum catalyst.
Depending on the type of system to which it is applied, the present method of hydrosilylation can also dramatically improve the yield of the target product and/or increase the reaction rate in addition to improving selectivity.
The components (a), (b), (c), and (d) used in the present method are described below.
The aforementioned (a) unsaturated compounds with terminal unsaturated groups refer to compounds having reactive carbon-carbon double bonds or carbon-carbon triple bonds at the terminals of the molecule. They are typically selected from among (1) through (8) below. These may include atoms selected from O, N, F, Cl, Br, Si, or S in addition to carbon atoms and hydrogen atoms in the structure, provided that the reactivity with the silane compound (b) above is not dramatically reduced. Component (a) can be, for example,
(1) styrene or styrene derivatives;
(2) vinylsilane compounds;
(3) silox
Tachikawa Mamoru
Takei Kasumi
Dow Corning Asia Ltd.
Gobrogge Roger E.
Shaver Paul F.
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