| PATENT ASSIGNEE'S COUNTRY | Japan |
| UPDATE | 05.00 |
| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | 09.05.00 |
| PATENT TITLE |
Method for manufacturing an acyloxysilane compound having functional groups bonded to silicon atoms via SI--C bonds |
| PATENT ABSTRACT |
A method of manufacturing acyloxysilane compounds having functional groups bonded to a silicon atom via Si--C bonds comprising reacting in a hydrosilation reaction an unsaturated compound (a) selected from the group consisting of (i) styrene or styrene derivative, (ii) vinylsilane compound, (iii) siloxane compound having a vinyl group bonded directly to a silicon atom, (iv) epoxy-functional olefin, (v) diene compound, (vi) allyl compound described by formula CH.sub.2 .dbd.CHCH.sub.2 X, where X is a halogen atom, an alkoxy group, or an acyloxy group, (vii) olefin compound having a terminal vinyl group, and (viii) acetylene-type compound with a silicon compound (b) that contains hydrogen atom bonded to the silicon atom and acyloxy group in the presence of a platinum catalyst. |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | 14.09.99 |
| PATENT FOREIGN APPLICATION PRIORITY DATA | This data is not available for free |
| PATENT REFERENCES CITED | This data is not available for free |
| PATENT CLAIMS |
We claim: 1. A method of manufacturing acyloxysilane compounds having functional groups bonded to a silicon atom via Si--C bonds comprising reacting in a hydrosilation reaction an unsaturated compound (a) selected from the group consisting of (i) styrene or styrene derivative, (ii) vinylsilane compound, (iii) siloxane compound having a vinyl group bonded directly to a silicon atom, (iv) epoxy-functional olefin, (v) diene compound, (vi) allyl compound described by formula CH.sub.2 .dbd.CHCH.sub.2 X, where X is a halogen atom, an alkoxy group, or an acyloxy group, (vii) olefin compound having a terminal vinyl group, and (viii) acetylene-type compound with a silicon compound (b) represented by general formula HSiR.sub.2 (O.sub.2 CR') where each R is independently selected from the group consisting of an organic group, a siloxy group, and a siloxanoxy group and R' is a hydrogen atom or an organic group in the presence of a platinum catalyst. 2. The method of claim 1, where in the silicon compound R selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a siloxy group, and a siloxanoxy group, and R' is an alkyl group having 1 to 6 carbon atoms or a hydrogen atom. 3. The method of claim 1, where the silicon compound is dimethylacetoxysilane. 4. The method of claim 1, where the unsaturated compound is selected from the group consisting of parachlorostyrene, divinylbenzene, octene-1, hexene-1, 1,3-divinyltetramethyl-1,3-disiloxane, vinylcyclohexene oxide, allylmethacrylate, allylchloride, .alpha.,.omega.-divinylpolydimethylsiloxane, styrene, and allylacetate. -------------------------------------------------------------------------------- |
| PATENT DESCRIPTION |
BACKGROUND OF INVENTION The present invention is a method of manufacturing siloxane or silane compounds which contain acyloxy groups which are important for efficient treatment of surfaces of inorganic solid bodies, for introduction of functional silyl groups or functional siloxanoxy groups into siloxane polymers, organic polymers, or similar polymers, as well as for use as functional groups of siloxanes curable by atmospheric moisture. Polymers or compounds having silyl groups directly bonded to hydrolyzable functional groups such as alkoxysilyl groups, chlorosilyl groups, etc., find important industrial application as modified silicone-type raw materials used for treating surfaces by hydrolyzing the functional groups followed by the formation of siloxane bonds by dehydration and condensation, or for curing by formation of cross-linking bonds between polymers. As a rule, silyl groups having hydrolyzable functional groups, such as alkoxysilyl groups, chlorosilyl groups, etc., are produced by hydrosilation of unsaturated organic compounds or polymers having unsaturated groups with hydroalkoxysilanes, or hydrochlorosilanes. However, such reactions of hydrosilation of the aforementioned hydrosilane compounds are often characterized by a slow reaction rate, requires a large amount of catalysts, and takes considerable time. Typically, such reactions have poor selectivity and the product is produced as a mixture of isomers. Furthermore in order to maintain catalytic activity, hydrosilation reactions with hydroalkoxysilanes or hydrochlorosilanes often require the presence of oxygen. This is dangerous because it may cause explosion or fire. Japanese Laid-Open Patent Application (Hei) 9-31414 describes hydrosilation of a vinyl group which is present in polyimide formed by reacting tetracarboxylic acid dianhydride and a diaminopolysiloxaneo having a side vinyl group. The aforementioned hydrosilation reaction is conducted with the use of a hydrosilane represented by the following formula: X.sub.3-t SiH(R.sup.9).sub.t, where R.sup.9 is an alkyl group having 1 to 6 carbon atoms, X is a hydrolyzable group, except for an alkoxy group, and t is an integer from 0 to 2. Examples of the aforementioned hydrosilanes are methyldiacetoxysilane and triacetoxysilane. Practical examples of the aforementioned publication refer to the use of methyldiacetoxysilane. The present inventors have unexpectedly found that the aforementioned methyldiacetoxysilane and triacetoxysilane possess extremely poor hydrosilation activity with respect to various olefin-type unsaturated compounds and acetylene-type unsaturated compounds, as well as to polyimides having olefin-type unsaturated side groups. In other words, it was unexpectedly found that hydro (monoacyloxy)silanes possess extremely high activity with respect to the last-mentioned olefin-type unsaturated compounds and acetylene-type unsaturated compounds. It is an object of the present invention to solve the problems associated with hydrosilation involving the use of the aforementioned hydroalkoxysilane, hydrochlorosilane, or hydrodiacyloxysilane and hydrotriacyloxysilane, more specifically the problem associated with low activity during the hydrosilation reaction. Another object is to solve the problem associated with low regio-selectivity in the aforementioned reaction. More specifically, it is an object of the present invention to provide a method for performing the hydrosilation reaction efficiently and economically with regard to the reaction time and catalyst activity, as well as to improve regio-selectivity in the reaction. Another object of the invention is to make it possible to conduct the hydrosilation reaction in an inert environment and under low oxygen partial pressure due to high catalytic activity and extended catalyst activity, thus reducing the danger of explosion and fire in conducting the hydrosilation reaction. The present inventors have found that silyl compounds can be produced with high yield at a high reaction rate and with high position selectivity by producing functional silane compounds by carrying out a hydrosilation reaction with the use of a platinum catalyst between Si--H functional silane compounds and various olefin-functional or acetylene-functional unsaturated compounds (the aforementioned compounds differ from polyimides derived from diaminopolysiloxane having olefin-type unsaturated side groups). The aforementioned effects are achieved by having in the aforementioned Si--H functional silicon compound one acyloxy group bonded directly to the aforementioned silicon atom. It has been found that the above-described hydrosilation reaction can be rapidly carried out under low partial oxygen pressure or without the presence of oxygen. SUMMARY OF INVENTION The present invention is a method of manufacturing acyloxysilane compounds having functional groups bonded to a silicon atom via Si--C bonds comprising reacting in a hydrosilation reaction an unsaturated compound (a) selected from the group consisting of (i) styrene or styrene derivative, (ii) vinylsilane compound, (iii) siloxane compound having a vinyl group bonded directly to a silicon atom, (iv) epoxy-functional olefin, (v) diene compound, (vi) allyl compound described by formula CH.sub.2 .dbd.CHCH.sub.2 X, where X is a halogen atom, an alkoxy group, or an acyloxy group, (vii) olefin compound having a terminal vinyl group, and (viii) acetylene-type compound with a silicon compound (b) that contains a hydrogen atom bonded to a silicon atom and an acyloxy group, represented by general formula HSiR.sub.2 (O.sub.2 CR'), where each R is independently selected from the group consisting of an organic group, a siloxy group, and a siloxanoxy group and R' is a hydrogen atom or an organic group in the presence of a platinum catalyst. DESCRIPTION OF INVENTION The present invention is a method of manufacturing acyloxysilane compounds having functional groups bonded to a silicon atom via Si--C bonds comprising reacting in a hydrosilation reaction an unsaturated compound (a) selected from the group consisting of (i) styrene or styrene derivative, (ii) vinylsilane compound, (iii) siloxane compound having a vinyl group bonded directly to a silicon atom, (iv) epoxy-functional olefin, (v) diene compound, (vi) allyl compound described by formula CH.sub.2 .dbd.CHCH.sub.2 X, where X is a halogen atom, an alkoxy group, or an acyloxy group, (vii) olefin compound having a terminal vinyl group, and (viii) acetylene-type compound with a silicon compound (b) that contains hydrogen atom bonded to a silicon atom and an acyloxy group, represented by general formula HSiR.sub.2 (O.sub.2 CR') (1), where each R is independently selected from the group consisting of an organic group, a siloxy group, and a siloxanoxy group and R' is a hydrogen atom or an organic group in the presence of a platinum catalyst. The aforementioned unsaturated compound (a) can be selected from compounds (i)-(viii). As far as these compounds decrease extremely reactivity with the hydro(acyloxy) group containing silicon compound, they may contain in the structure, atom selected from O, N, F, Cl, Br, Si, or S in addition to carbon and hydrogen. The following are specific examples of aforementioned styrenes and styrene derivatives: styrene-type hydrocarbons, such as styrene, p-methylstyrene, p-ethylstyrene, p-phenylstyrene, and divinylbenzene; halogen-containing styrene, such as p-fluorostyrene, p-chlorostyrene, p-bromostyrene, p-iodostyrene, and p- and n-(chloromethyl) styrene; oxygen- or silicon-containing styrene derivatives, such as p-methoxystyrene and p-trimethylsilylstyrene; nitrogen-containing styrene derivatives, such as p-(diphenylamino) styrene, p-(ditolylamino) styrene, p-(dixylylamino) styrene, and bis (4-vinylphenyl) (4-methylphenyl) amine. The following are examples of vinylsilane compounds and siloxane compounds having vinyl groups directly bonded to silicon atoms: vinyltrialkylsilanes, such as vinyltrimethylsilane, vinyltriethylsilane, vinyltripropylsilane, and vinyldimethylethylsilane; vinylalkoxysilanes, such as vinyltrimethoxysilane, vinyltriethoxysilane, vinylmethyldiethoxysilane, and vinyldimethylmethoxysilane; vinyl-functional siloxanes, such as 1,3-divinyltetramethylsiloxane, .alpha., .omega.-divinylpolydimethylsiloxane, and 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane; and vinyl-functional silazanes, such as 1,3-divinyltetramethyldisilazane, and 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasilazane. The aforementioned epoxy-functional olefins can be, for example, allylglycidyl ether and vinylcyclohexene oxide. The aforementioned diene compounds can be, for example, 1,3-butadiene, isoprene, 1,5-hexadiene, 1,3-octadiene, and 1,3-cyclohexadiene. The aforementioned allyl compound of the following formula: CH.sub.2 .dbd.CHCH.sub.2 X can be exemplified by allyl chloride, allyl acetate, and allyl methacrylate. The aforementioned olefin compounds having vinyl terminal groups may have either a linear or a branched structure. They also may also be substituted with aromatic hydrocarbon groups. The following are examples of terminal-unsaturated olefin compounds of linear chain type: ethylene, propylene, butene-1, hexene-1, octene-1, and octadecene-1. The following are examples of branched olefin compounds having terminal-unsaturated groups: isobutylene, 3-methylbutene-1, 3,5-dimethylhexane-1, and 4-ethyloctane-1. The following are examples of the aforementioned olefin compounds having vinyl terminal groups which contain an atom selected from the group consisting of O, N, F, Cl, Br, Si, S: an oxygen-containing allyl compound such as allylmethacrylate; an amine compound containing a vinyl group, such as N-vinylcarbazole; an olefin halide compound, such as 4-chlorobutene-1 and 6-bromohexene-1; silicon-functional olefin compound, such as aryloxytrimethylsilane; sulfur-containing olefin compound, such as allylmercaptane and allyl sulfide. In the case when an aromatic hydrocarbon group is present in the aforementioned olefin compound, the latter can be represented by allylbenzene and 4-vinylbutene-1. The aforementioned acetylene-type compound may have at its terminal an ethynyl group represented by formula (CH.tbd.C--) or may have within the molecule an ethynylene group of formula (--C.tbd.C--). These compounds may be substituted with aromatic hydrocarbon groups. The following are examples of ethylene-type compounds having an ethynyl group (CH.tbd.C--) at their terminal: acetylene, propyne, butene-1, hexyne-1, and octyne-1. The acetylene-type compounds, which have ethynylene group of formula (--C.tbd.C--) within the molecules, can be exemplified by the following: butyne-2, hexyne-2, hexyne-3, and octyne-4. The acetylene-type compounds having aromatic hydrocarbon groups can be represented by the following: phenylacetylene, 3-phenylpropene, and 4-phenylbutene-1. Examples of the aforementioned acetylene compounds which contain atoms selected from the group containing O, N, F, Cl, Br, Si, S are as follows: 3-methyl-1-butene-3-ol and 3-phenyl-1-butene-3-ol; silicon-containing acetylene-type compound, such as trimethylsilyl adduct of 3-methyl-1-butyne-3-ol (HC.tbd.C--CH(CH.sub.3)--O--Si(CH.sub.3).sub.3) and trimethylsilyl adduct of 3-phenyl-1-butyne-3-ol (HC.tbd.C--CH(C.sub.6 H.sub.5)--O--Si(CH.sub.3).sub.3); and halogen acetylene-type compound, such as propargyl chloride and propargyl bromide. Silicon compound (b) of the present invention is described by general formula HSiR.sub.2 (O.sub.2 CR') (1), where each R is independently selected from the group consisting of an organic group, a siloxy group, and a siloxanoxy group; and R' is a hydrogen atom or an organic group. When R is an organic group, R can be for example, an alkyl group, alkenyl group, aryl group, halogenated alkyl group, halogenated aryl group, alkoxy group, and aryloxy group. For example, R can be: (1) an alkyl group having 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, cyclohexyl, n-octyl, undecyl, and heptadecyl; (2) an alkenyl group having 2 to 18 carbon atoms, such as propenyl and butenyl; (3) an aryl group having 6 to 18 carbon atoms, such as phenyl; (4) a halogenated alkyl group having 1 to 18 carbon atoms (the halogen atom can be F, Cl, or Br), such as a chloromethyl, fluoromethyl, and 3,3,3-trifluoropropyl; (5) a halogenated aryl group having 6 to 10 carbon atoms (the halogen atom can be F, Cl, or Br) such as a p-chlorophenyl; (6) an alkoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, cyclopentyloxy, cyclohexyloxy, 2-methoxyethoxy, and 2-ethoxyethoxy; and (7) an aryloxy group having 6 to 10 carbon atoms, such as a phenoxy group. If the number of carbon atoms exceeds the recommended range, it would be impractical since the activity of the respective compounds will be reduced. In the case where R is a siloxy group, R can be for example trimethylsiloxy, triethylsiloxy, phenyldimethylsiloxy, diphenylmethylsiloxy, and (3,3,3-trifluoropropyl) dimethylsiloxy. In the case where R is a siloxanoxy group, R can be, for example, a structure having the main chain in the form of a polydimethylsiloxane having a terminal siloxy group such as a trimethylsiloxy or a terminal capped with --SiH(CH.sub.3)(OC(.dbd.O)CH.sub.3). From the practical point of view, it is recommended that, in terms of a degree of polymerization (i.e., a number-average degree of polymerization) of siloxane units of siloxanoxy groups, the degree of polymerization be below 1,000 and preferably, below 500. R' is a hydrogen atom or an organic group. When R' is an organic group, it is preferably selected from the following groups: an alkyl group having 1-18 carbon atoms; an aryl group having 6-10 carbon atoms; a halogenated alkyl group having 1-18 carbon atoms; and a halogenated aryl group having 6-10 carbon atoms. The principle of the invention will not be violated if the aforementioned organic group is substituted with oxygen or silicon atoms. The following are examples of the aforementioned compounds: an alkyl group having 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-butyl, n-pentyl, cyclohexyl, n-octyl, undecyl, and heptadecyl; an aryl group having 6 to 10 carbon atoms, such as phenyl, tolyl, xylyl, and naphthyl; a halogenated alkyl group having 1 to 18 carbon atoms, such as chloromethyl, dichloromethyl, trichloromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl; and a halogenated aryl group having 6 to 10 carbon atoms such as p-chlorophenyl. The following are examples of organic groups where R' comprises an organic group having an oxygen and silicon atom --CH.sub.2 --C--(.dbd.O)--OSiR.sub.2 H and --C.sub.6 H.sub.3 (C(.dbd.O)OSiR.sub.2 H).sub.2, where R has the same meaning as has been specified for organic groups in formula (1). The following are specific examples of compounds represented by formula (1): hydro(formyloxy)silanes, such as dimethylformyloxysilane, diethylformyloxysilane, dipropylformyloxysilane, diisopropylformyloxysilane, methylethylformyloxysilane, methylphenylformyloxysilane, methylpropylformyloxysilane, diphenylformyloxysilane, methylmethoxyformyloxysilane, methylethoxyformyloxysilane, and methyl (trimethylsiloxy)formyloxysilane; hydro(acetoxy)silanes, such as dimethylacetoxy silane, diethylacetoxysilane, dipropylacetoxysilane, diisopropylacetoxysilane, methylethylacetoxysilane, methylphenylacetoxysilane, methylpropylacetoxysilane, diphenylacetoxysilane, methylmethoxyacetoxysilane, methylethoxyacetoxysilane, diethoxyacetoxysilane, and methyl(trimethylsiloxy)acetoxysilane; hydro(propionyloxy) silanes, such as dimethylpropionyloxysilane, diethylpropionyloxysilane, dipropylpropionyloxysilane, diisopropylpropionyloxysilane, methylethylpropionyloxysilane, ethylphenylpropionyloxysilane, methylpropylpropionyloxysilane, biphenylpropionyloxysilane, diphynylpropionyloxysilane, methylmethoxypropionyloxysilane, methylethoxypropionyloxysilane, and methyl(trimethylsiloxy) propionyloxysilane; hydro(butyryloxy)silanes, such as dimethylbutyryloxysilane, diethylbutyryloxysilane, dipropylbutyryloxysilane, diisopropylbutyryloxysilane, methylethylbutyryloxysilane, methylphenylbutyryloxysilane, methylpropylbutyryloxysilane, diphenylbutyryloxy silane, methylmethoxybutyryloxysilane, methylethoxybutyryloxysilane, and methyl (trimethylsiloxy)butyryloxysilane. The following are specific examples of compounds represented by formula (1): hydro(lauroyloxy)silane, hydro(stearoyloxy)silane, hydro(benzoyloxy)silane, hydro (chloroacetoxy)silane, hydro(dichloroacetoxy)silane, hydro(trichloroacetoxy)silane, hydro(trifluoroacetoxy)silane, hydro(benzoyloxy)silane, and dimethylsilyl esters of isobutyric acid. The aforementioned hydro(lauroyloxy)silanes can be, for example, dimethyl-lauroyloxysilane, methylphenyl-lauroyloxysilane, diphenyl-lauroyloxysilane, methylmethoxy-lauroyloxysilane, methylethoxy-lauroyloxysilane, and methyl (trimethylsiloxy)lauroyloxysilane; the aforementioned hydro(stearoyloxy)silanes can be, for example, dimethyl(methylphenyl)stearoyloxy silane, diphenylstearoyloxysilane, methylmethoxystearoyloxysilane, methylethoxystearoyloxysilane, and methyl-(trimethylsiloxy)stearoyloxysilane; the aforementioned hydro(benzoyloxy)silanes can be, for example, dimethylbenozoyloxysilane, methylphenylbenozoyloxysilane, diphenyl benozoyloxysilane, methylmethoxybenozoyloxy silane, methylethoxybenozoyloxy silane, and methyl(trimethylsiloxy)benozoyloxysilane; the aforementioned hydro (chloroacetoxy)silanes can be, for example, dimethyl(chloroacetoxy)silane, methylphenyl (chloroacetoxy)silane, diphenyl(chloroacetoxy)silane, methylmethoxy(chloroacetoxy) silane, methylethoxy(chloroacetoxy)silane, and methyl(trimethylsiloxy)(chloroacetoxy) silane; the aforementioned hydro(dichloroacetoxy)silanes can be, for example, dimethyl (dichloroacetoxy)silane, methylphenyl(dichloroacetoxy)silane, diphenyl (dichloroacetoxy)silane, methylmethoxy(dichloroacetoxy)silane, methylethoxy (dichloroacetoxy)silane, and methyl(trimethylsiloxy)(dichloroacetoxy)silane; the aforementioned hydro(trichloroacetoxy)silanes can be, for example, dimethyl (trichloroacetoxy)silane, methylphenyl(trichloroacetoxy)silane, diphenyl (trichloroacetoxy)silane, methylmethoxy(trichloroacetoxy)silane, methylethoxy (trichloroacetoxy)silane, and methyl(trimethylsiloxy)(trichloroacetoxy)silane; the aforementioned hydro(trifluoroacetoxy)silanes can be, for example, dimethyl (trifluoroacetoxy)silane, methylphenyl(trifluoroacetoxy)silane, diphenyl (trifluoroacetoxy)silane, methylmethoxy(trifluoroacetoxy)silane, methylethoxy (trifluoroacetoxy)silane, and methyl(trimethylsiloxy)(trifluoroacetoxy)silane; the aforementioned hydro(benzoyloxy)silanes can be, for example, dimethylbenzoyloxy silane, methylphenylbenzoyloxysilane, diphenylbenzoyloxysilane, methylmethoxy benzoyloxysilane, methylethoxybenzoyloxysilane, and methyl(trimethylsiloxy)benzoyloxy silane. In addition to the above, dimethylsilyl esters of the following acids can be used: isobutyric acid, valeric acid, pivalic acid, hexanoic acid, cyclohexanoic carboxylic acid, nonanic acid, toluic acid, naphthoic acid, parachlorobenzoic acid, maronic acid, succinic acid, glutamic acid, terephthalic acid, trimesic acid, or a similar mono-, di-, or tricarboxylic acid. In view of better availability and for an increase in the production yield, it is preferable to select such silicon compounds with hydrogen atom bonded to the silicon and acyloxy group, which have R in formula (1) in the form of an alkyl group having 1 to 6 carbon atoms, a siloxanoxy group, a siloxy group, or an alkoxy group having 1 to 6 carbon atoms; with R' being preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. An acyloxysilane compound having functional group bonded to a silicon atom via Si--C bond obtained by the present method may have silane structure or polysiloxane structure, depending on the structure of the silicon compound (b) with hydrogen atom bonded to the silicon and acyloxy group as a starting material. In other words, when R in general formula (1): HSiR.sub.2 (O.sub.2 CR') is an organic group, the obtained acyloxysilane compound will have a silane structure, and when R in the aforementioned formula is a siloxy group or a siloxanoxy group, the obtained compound will have a polysiloxane structure. For the convenience of the description, in the present patent application, the term "acyloxysilane compound having a functional group bonded to a silicon atom via a Si--C bond" covers both acyloxysilanes with aforementioned functional groups and acyloxypolysiloxanes with aforementioned functional groups. The hydrosilation reaction of the present invention can be carried out at a temperature between 10.degree. C. and 250.degree. C. However, for achieving an appropriate reaction rate and for stable existence of substances participating in the reaction and of the obtained products, it is recommended that the temperature be between 20.degree. C. and 200.degree. C. The use of solvents is not generally necessary for the purposes of the present invention. However, in order to dissolve some substances, facilitate control of the reaction temperature, and addition of catalytic components, solvents for hydrocarbon-type compounds or solvents for catalytic components can be used. Solvents most suitable for the above purposes are saturated or unsaturated hydrocarbon compounds, such as hexane, cyclohexane, heptane, octane, dodecane, benzene, toluene, xylene, dodecylbenzene; as well as halogenated hydrocarbon compounds, such as chloroform, methylene chloride, chlorobenzene, and orthodichlorobenzene. Hydrosilation catalysts suitable for the purposes of the present invention are exemplified by a 0-valence platinum-olefin complex, a 0-valence platinum-vinylsiloxane complex, a halogenated bivalent platinum-olefin complex, chloroplatinic acid, and platinum supported on a carrier such as carbon or silica. The invention will be further described in more detail with reference to practical examples, which, however, should not be construed as limiting the scope of the present invention. In the description of characteristics of the products given in the examples below, GC designates "gas chromatography", GC-MS designates "gas chromatography--mass spectroscopy". Me stands for "methyl group", OAc stands for "acetoxy group", and Ph stands for "phenyl group". Acyloxysilane compounds, alkylsilane compounds, and siloxane compounds used in the practical examples given below are either commercially available or synthesized by methods known in the art. Unsaturated compounds were used in the form in which they were commercially obtained. The following is a description of Practical and Comparative examples. |
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