WO2009142161A1 - ポリシラン化合物の製造方法 - Google Patents
ポリシラン化合物の製造方法 Download PDFInfo
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- WO2009142161A1 WO2009142161A1 PCT/JP2009/059082 JP2009059082W WO2009142161A1 WO 2009142161 A1 WO2009142161 A1 WO 2009142161A1 JP 2009059082 W JP2009059082 W JP 2009059082W WO 2009142161 A1 WO2009142161 A1 WO 2009142161A1
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- polydimethylsilane
- polydiphenylsilane
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- surfactant
- alkali metal
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/32—Post-polymerisation treatment
- C08G77/34—Purification
Definitions
- the present invention relates to a method for producing polydimethylsilane or polydiphenylsilane. More specifically, the present invention relates to a method for easily producing high-purity polydimethylsilane or polydiphenylsilane, which can efficiently remove by-products such as alkali metal salts and alkaline earth metal salts.
- Non-Patent Document 1 Non-Patent Document 2
- Polydimethylsilane or polydiphenylsilane obtained by catalytic reaction of dimethyldichlorosilane or diphenyldichlorosilane with an alkali metal in an organic solvent is a crystal that is insoluble in ordinary organic solvents and does not melt even when heated. It has the property to do. Furthermore, polydimethylsilane or polydiphenylsilane has high water repellency, so even if you try to wash the by-product alkali metal salts with water, polydimethylsilane or polydiphenylsilane floats on the surface of the water and the contact efficiency with water is very high. It ’s bad.
- An object of the present invention is to provide a method for easily producing high-purity polydimethylsilane or polydiphenylsilane, which can efficiently remove by-products such as alkali metal salts and alkaline earth metal salts.
- dimethyldichlorosilane or diphenyldichlorosilane (hereinafter, these compounds are collectively referred to as a raw material dichlorosilane compound) and an alkali metal and / or an alkaline earth metal.
- Reaction in an organic solvent yields crude polydimethylsilane or crude polydiphenylsilane, the alkali metal and alkaline earth metal in the crude polydimethylsilane or crude polydiphenylsilane are deactivated, and then crude polydimethylsilane or crude polydimethylsilane.
- the production method of the present invention makes it possible to easily obtain polydimethylsilane or polydiphenylsilane with high yield, low residual amount of by-products such as alkali metal salts and alkaline earth metal salts, and high purity.
- the obtained polydimethylsilane or polydiphenylsilane is suitable as an optical / electronic functional material such as a precursor of a silicon carbide material, an organic photoreceptor, an optical waveguide, and an optical memory.
- a raw dichlorosilane compound and an alkali metal and / or alkaline earth metal are reacted in an organic solvent to obtain crude polydimethylsilane or crude polydiphenylsilane.
- the method includes a step of deactivating alkali metal and alkaline earth metal in the crude polydimethylsilane or crude polydiphenylsilane, and then washing the crude polydimethylsilane or crude polydiphenylsilane with water in the presence of a surfactant.
- Examples of the alkali metal used in the present invention include lithium simple substance, sodium simple substance, potassium simple substance, and alloys thereof. Of these, sodium alone is particularly preferable.
- Examples of the alkaline earth metal used in the present invention include magnesium alone, calcium alone, barium alone, strontium alone, or alloys thereof. Of these, magnesium alone is preferred. The amount of alkali metal and alkaline earth metal used is slightly larger than the theoretical amount with respect to the raw material dichlorosilane compound.
- an alkali metal 2.0 to 2.4 molar equivalent is preferable, 2.1 to 2.2 molar equivalent is particularly preferable, and in the case of an alkaline earth metal, 1.0 to 1.2 Molar equivalents are preferred, with 1.05 to 1.1 molar equivalents being particularly preferred. If the amount used is 2.0 molar equivalents in the case of an alkali metal and less than 1.0 molar equivalents in the case of an alkaline earth metal, the reaction rate tends to decrease and the time required for the reaction tends to become longer.
- the amount used is 2.4 molar equivalents in the case of an alkali metal and more than 1.2 molar equivalents in the case of an alkaline earth metal, the alkali metal and / or alkaline earth metal remaining in the reaction product And the time required for the removal process tends to be longer.
- organic solvents used in the reaction include tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, anisole, 1,2-dimethoxyethane, diethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethyl ether, diisopropyl ether, and tert-butyl.
- Ether solvents such as methyl ether; aliphatic hydrocarbon solvents such as hexane, heptane, octane, and decane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, and mesitylene, and the like. A mixture of seeds or more can be used. Of these, aromatic hydrocarbon solvents are preferred.
- the reaction temperature between the raw material dichlorosilane compound and the alkali metal and / or alkaline earth metal is not particularly limited, but is preferably 98 ° C. to the solvent reflux temperature.
- the reaction is preferably performed in an atmosphere of an inert gas such as nitrogen, and can be performed under normal pressure or under pressure.
- the reaction method is not particularly limited. Specifically, first, an alkali metal and / or an alkaline earth metal is dispersed in the organic solvent, and the raw material dichlorosilane compound is added dropwise thereto with stirring. It is preferable to carry out. In order to complete the reaction, after completion of the dropwise addition of the starting dichlorosilane compound, stirring is preferably continued for 1 to 24 hours at the reaction temperature, more preferably 1 to 12 hours.
- the raw material dichlorosilane compound is polycondensed to obtain a liquid in which crude polydimethylsilane or crude polydiphenylsilane is dispersed in an organic solvent.
- the dispersion is cooled. Usually cooled to 40-80 ° C.
- the alkali metal and alkaline earth metal in the crude polydimethylsilane or the crude polydiphenylsilane are deactivated. Alcohol is usually used to deactivate alkali metals and alkaline earth metals.
- the alkali metal and Alkaline earth metals can be deactivated.
- the alcohol to be used include methanol, ethanol, isopropyl alcohol, n-propyl alcohol, 2-methylpropyl alcohol, n-butyl alcohol, t-butyl alcohol, ethylene glycol and the like. Of these, methanol is preferable.
- the amount of alcohol used is equal to the number of moles of remaining alkali metal or alkaline earth metal, equimolar in the case of alkali metal, double mole in the case of alkaline earth metal, or more. If it is, it will not be restrict
- metal sodium is used at 2.1 molar equivalents relative to dimethyldichlorosilane or diphenyldichlorosilane
- alcohol is preferably used at 0.1 to 0.5 molar equivalents, more preferably 0.2 to 0 More preferably, 3 molar equivalents are used.
- the liquid after deactivation can be hydrolyzed by adding water.
- the amount of water used is not particularly limited as long as it is sufficient for hydrolysis and dispersion of the polymer.
- a surfactant is dissolved in alcohol used for deactivation of the alkali metal and alkaline earth metal and / or in water used for hydrolysis. It is preferable to dissolve the surfactant.
- the dispersibility of the crude polydimethylsilane or the crude polydiphenylsilane is increased, and the contact efficiency with water in water washing described later is increased.
- surfactant used in the present invention examples include an anionic surfactant, a cationic surfactant, an amphoteric surfactant, and a nonionic surfactant.
- Anionic surfactants include fatty acid salts, alkylbenzene sulfonates, higher alcohol sulfates, polyoxyethylene alkyl ether sulfates, ⁇ -sulfo fatty acid esters, ⁇ -olefin sulfonates, monoalkyl phosphate esters, alkanes Examples thereof include sulfonates.
- Examples of the cationic surfactant include alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium salt, alkyl dimethyl benzyl ammonium salt and the like.
- Examples of amphoteric surfactants include alkyl amine oxides, alkyl betaines, alkyl carboxy betaines, and alkylamino fatty acid salts.
- Nonionic surfactants include polyoxyalkylene alkyl ether, polyoxyalkylene alkyl phenyl ether, alkyl glucoside, polyoxyethylene fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid alkanolamide, etc. Can be mentioned.
- anionic surfactants or nonionic surfactants are preferred, and nonionic surfactants are more preferred.
- the alkyl chain contained in the nonionic surfactant is preferably a carbon chain in the range of C 8 to C 20 and may be branched.
- nonionic surfactants polyoxyethylene propylene alkyl ether and polyoxyethylene propylene alkyl phenyl ether which are polyoxyalkylene alkyl ethers are preferable.
- the surfactant used in the present invention is not particularly limited by the HLB, but a surfactant having a high HLB is preferable.
- the HLB is preferably 5 to 20, more preferably 10 to 15, and still more preferably 12 to 15.
- the surfactant used in the present invention is not particularly limited by the cloud point.
- the cloud point is preferably 0 to 100 ° C., more preferably 20 to 95 ° C.
- it is preferable that the cloud point is in the vicinity of the water temperature at the time of water washing, specifically, a temperature range from 10 ° C. to 10 ° C. higher than the temperature at the time of water washing is preferred, and further 5 ° C. to 5 ° C. A temperature range is more preferred. *
- the addition amount of the surfactant is preferably 0.1 to 20 parts by mass, more preferably 0.6 to 8 parts by mass with respect to 129 parts by mass of dimethyldichlorosilane used as a raw material.
- Diphenyldichlorosilane used as a raw material The amount is preferably 0.2 to 40 parts by mass, more preferably 1 to 20 parts by mass with respect to 253 parts by mass. If the amount of the surfactant is too small, the crystals tend to float and the cleaning effect tends to decrease. Although a large amount of surfactant may be added, it is not economical because the effect is saturated.
- the reaction product solidifies into a slurry by the hydrolysis.
- the slurry containing the surfactant is washed with water.
- the addition of water may be performed after removing the organic solvent, may be performed while removing the organic solvent, or may be performed before removing the organic solvent. From the viewpoint of reducing the viscosity of the reaction product and reducing the stirring power, it is preferable to add water during the removal of the organic solvent or before the removal of the organic solvent.
- the removal method of an organic solvent is not specifically limited, For example, distillation, evaporation, etc. are mentioned.
- water washing it is preferable to add water at room temperature and warm or add warm water.
- the water temperature during washing is preferably 25 ° C. or higher, more preferably 40 to 80 ° C.
- the water used for the water washing can be removed by a known solid-liquid separation operation such as decantation or filtration.
- the number of times of water washing is not particularly limited, and can be appropriately selected according to the removal status of by-products such as alkali metal salts and alkaline earth metal salts.
- the polydimethylsilane or polydiphenylsilane obtained by the production method of the present invention is usually insoluble in organic solvents and acids / alkalis.
- the molecular weight of polydimethylsilane or polydiphenylsilane obtained by the production method of the present invention is not particularly limited.
- polydimethylsilane or polydiphenylsilane having an appropriate molecular weight can be produced by the production method of the present invention.
- “Development of organosilicon polymer” (supervised by Hideki Sakurai, page 106, CMC Publishing Co., Ltd.) describes polydimethylsilane having a number average molecular weight of 2580 and a weight average molecular weight of 4650. Polydimethylsilane having such a molecular weight can also be produced by the production method.
- the molecular weight of polydimethylsilane or polydiphenylsilane can be determined by ultra high temperature GPC.
- Example 1 The interior of a four-necked flask equipped with a motor stirrer, thermometer, dropping funnel and reflux condenser was purged with nitrogen. The flask was charged with 24 parts by mass (1.05 mol parts) of metallic sodium and 62 parts by mass of toluene (specific gravity: 0.867), and heated to 110 ° C. or higher to melt the metallic sodium. The molten metallic sodium was dispersed by vigorous stirring. While maintaining the reflux state, 64.5 parts by mass (0.5 mol part) of dimethyldichlorosilane was added dropwise to the flask over 8 hours. The contents gradually turned blackish purple. After completion of dropping, the reflux state was maintained for 8 hours under stirring. A black purple slurry was obtained.
- the slurry was filtered under reduced pressure, and the aqueous phase containing alkali metal salts and the like as reaction byproducts was discharged. 100 mass parts of 40 ° C. warm water was added to the separated solid and stirred for 30 minutes. Filtration under reduced pressure gave a solid. This water washing operation was performed 5 times in total. Subsequently, washing with 47.58 parts by mass of methanol (specific gravity: 0.793) and washing with 52.0 parts by mass of toluene (specific gravity: 0.867) were performed three times in the manner of this water washing operation. The obtained solid content was taken out from the filtration device and dried. 25 parts by weight of white polydimethylsilane (yield 86%) was obtained. The sodium chloride content remaining in the polydimethylsilane was 100 ppm or less.
- Example 2 Polydimethylsilane was obtained in the same manner as in Example 1 except that 13 parts by mass were dropped over 30 minutes and the water washing operation was performed 20 times in total. The yield was 85%.
- the reaction mixture gradually solidified while a 5% aqueous solution of a nonionic surfactant was being added dropwise.
- Polydimethylsilane was obtained in the same manner as in Example 2 except that it was changed to a 5% aqueous solution of (sodium n-dodecyl benzene sulfonate (Taika Power LN2050D, manufactured by Teica)). The yield was 80%. However, the dispersibility at the time of washing with water was low, and when the stirring was stopped, the solid content separated into the upper part. In the eighth and subsequent water washings, crystals floated on the water surface, but the sodium chloride content in polydimethylsilane was about 100 ppm.
- the polydimethylsilane or polydiphenylsilane obtained by the production method of the present invention is suitable as an optical / electronic functional material such as a precursor of a silicon carbide material, an organic photoreceptor, an optical waveguide, and an optical memory.
- the polydimethylsilane or polydiphenylsilane obtained by the production method of the present invention can also be used for ceramic raw materials, conductive materials, and light-related materials (resist materials).
- polydimethylsilane or polydiphenylsilane obtained by the production method of the present invention is subjected to melt spinning, infusibilization, heat treatment (firing), or polydimethylsilane or polydiphenyl obtained by the production method of the present invention.
- silane and pyrolysis-disappearing resin By blending silane and pyrolysis-disappearing resin, the blend is melt-spun, infusibilized, and heat-treated (fired), so there is no change in tensile strength and elastic modulus from low to high temperatures and excellent oxidation resistance.
- a thin silicon carbide fiber having a very low reactivity with a metal This silicon carbide fiber can be used as a catalyst carrier used for an exhaust gas filter of a diesel engine, etc., as a composite material excellent in heat resistance and mechanical strength by being combined with resin, ceramics, metal, or the like.
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Abstract
Description
アルカリ金属イオンが残存したポリシラン化合物を炭化ケイ素材料の前駆体として使用すると、加熱処理で使用される熱分解槽を腐食させる恐れがあり、光導波路電子材料の用途においては伝播損失等を引き起こす恐れがある。さらに、未反応アルカリ金属が残存していると、濾過時に水分や湿気によって、発火する恐れもある。
本発明の目的は、アルカリ金属塩やアルカリ土類金属塩等の副生物を効率的に除去でき、高純度のポリジメチルシランまたはポリジフェニルシランを容易に製造する方法を提供することにある。
アルカリ金属およびアルカリ土類金属の使用量は、原料ジクロロシラン化合物に対して理論量より若干過剰量である。具体的にはアルカリ金属の場合は、2.0~2.4モル当量が好ましく、2.1~2.2モル当量が特に好ましく、アルカリ土類金属の場合は、1.0~1.2モル当量が好ましく、1.05~1.1モル当量が特に好ましい。使用量がアルカリ金属の場合には2.0モル当量、アルカリ土類金属の場合には1.0モル当量より少ない場合、反応速度が低下し、反応に必要な時間が長くなる傾向になる。また、使用量がアルカリ金属の場合には2.4モル当量、アルカリ土類金属の場合には1.2モル当量よりも多い場合、反応生成物中に残るアルカリ金属および/またはアルカリ土類金属が多くなり、除去工程に要する時間が長くなる傾向になる。
該反応方法は特に限定されないが、具体的には、まず前記有機溶媒にアルカリ金属および/またはアルカリ土類金属を分散させ、そして、これに攪拌下、原料ジクロロシラン化合物を滴下して、反応を行わせることが好ましい。
反応を完結させるために、原料ジクロロシラン化合物の滴下終了後、前記反応温度で1~24時間撹拌を継続することが好ましく、1~12時間撹拌を継続することがより好ましい。
アニオン界面活性剤としては、脂肪酸塩、アルキルベンゼンスルホン酸塩、高級アルコール硫酸エステル塩、ポリオキシエチレンアルキルエーテル硫酸塩、α-スルホ脂肪酸エステル、α-オレフィンスルホン酸塩、モノアルキルリン酸エステル塩、アルカンスルホン酸塩などが挙げられる。
カチオン界面活性剤としては、アルキルトリメチルアンモニウム塩、ジアルキルジメチルアンモニウム塩、アルキルジメチルベンジルアンモニウム塩などが挙げられる。
両性界面活性剤としては、アルキルアミンオキシド、アルキルベタイン、アルキルカルボキシベタイン、アルキルアミノ脂肪酸塩などが挙げられる。
ノニオン界面活性剤としては、ポリオキシアルキレンアルキルエーテル、ポリオキシアルキレンアルキルフェニルエーテル、アルキルグルコシド、ポリオキシエチレン脂肪酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、脂肪酸アルカノールアミドなどが挙げられる。
これらのうち、アニオン界面活性剤またはノニオン界面活性剤が好ましく、ノニオン界面活性剤がより好ましい。ノニオン界面活性剤中に含まれるアルキル鎖はC8~C20の範囲の炭素鎖が好ましく、分岐していても良い。ノニオン界面活性剤の中でも、ポリオキシアルキレンアルキルエーテルであるポリオキシエチレンプロピレンアルキルエーテル、ポリオキシエチレンプロピレンアルキルフェニルエーテルが好ましい。
モーター攪拌機、温度計、滴下ロート、還流コンデンサーを備えた4つ口フラスコの内部を窒素置換した。該フラスコに、金属ナトリウム24質量部(1.05mol部)、およびトルエン62質量部(比重:0.867)を仕込み、110℃以上に加熱して金属ナトリウムを融解させた。激しく撹拌して融解した金属ナトリウムを分散させた。還流状態を維持したまま、ジメチルジクロロシラン64.5質量部(0.5mol部)を8時間掛けてフラスコに滴下した。内容物は徐々に黒紫色に変色した。滴下終了後、攪拌下、還流状態を8時間保持した。黒紫色のスラリーが得られた。
ノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))のメタノール溶液を滴下する代わりに、メタノール3.2質量部(0.1mol部)を30分間かけて滴下し、次いでノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液13質量部を30分間かけて滴下し、水洗浄操作を合計20回行った他は実施例1と同じ方法で、ポリジメチルシランを得た。収率は85%であった。
実施例2では、ノニオン界面活性剤の5%水溶液を滴下している最中に反応混合物が徐々に固化した。また、水洗浄時に少量の結晶が浮き上がっていたが、ポリジメチルシラン中の塩化ナトリウム含量は約100ppmであった。
ノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液の滴下を行わなかった他は実施例2と同じ方法でポリジメチルシランを得た。収率は88%であった。ポリジメチルシラン中の塩化ナトリウム含量は800ppm以上であった。
実施例2で用いられたノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液を、ノニオン界面活性剤(ポリオキシエチレングリコールエステル、HLB=5.5(アデカノールNK-3、(株)ADEKA製))の5%水溶液に替えた他は実施例2と同じ方法で、ポリジメチルシランを得た。収率は84%であった。8回目以降の水洗浄では結晶が水面に浮き上がっていたが、ポリジメチルシラン中の塩化ナトリウム含量は約100ppmであった。
実施例2で用いられたノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液を、ノニオン界面活性剤(ポリオキシエチレングリコールエステル、HLB=9.0(アデカノールNK-4、(株)ADEKA製))の5%水溶液に替えた他は実施例2と同じ方法で、ポリジメチルシランを得た。収率は80%であった。8回目以降の水洗浄では結晶が水面に浮き上がっていたが、ポリジメチルシラン中の塩化ナトリウム含量は約100ppmであった。
実施例2で用いられたノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液を、ノニオン界面活性剤(ポリオキシエチレンオクチルフェニルエーテル、HLB=13.5、曇点65℃(Triton X-100, UCC and Plastic社製)の5%水溶液に替えた他は実施例2と同じ方法で、ポリジメチルシランを得た。水洗浄時の分散性は非常に良く、結晶が水面に浮き上がることはなかった。ポリジメチルシラン中の塩化ナトリウム含量は100ppm以下であった。収率は80%であった。
実施例2で用いられたノニオン界面活性剤(ポリオキシアルキレンアルキルエーテル、HLB=14.1、曇点65℃(ニューカルゲン D-1110DIR 竹本油脂社製))の5%水溶液を、アニオン界面活性剤(n-ドデシルベンセンスルホン酸ナトリウム (テイカパワー LN2050D、テイカ社製))の5%水溶液に替えた他は実施例2と同じ方法で、ポリジメチルシランを得た。収率は80%であった。ただし、水洗浄時の分散性は低く、攪拌を停止すると固形分は上部に分離した。8回目以降の水洗浄では結晶が水面に浮き上がっていたが、ポリジメチルシラン中の塩化ナトリウム含量は約100ppmであった。
本出願は、2008年5月20日出願の日本特許出願(特願2008-131899)および2008年5月27日出願の日本特許出願(特願2008-137429)に基づくものであり、その内容はここに参照として取り込まれる。
Claims (4)
- ジメチルジクロロシランまたはジフェニルジクロロシランとアルカリ金属および/またはアルカリ土類金属とを有機溶媒中で反応させて粗ポリジメチルシランまたは粗ポリジフェニルシランを得、該粗ポリジメチルシランまたは粗ポリジフェニルシラン中のアルカリ金属およびアルカリ土類金属を失活させ、次いで粗ポリジメチルシランまたは粗ポリジフェニルシランを界面活性剤の存在下に水洗浄する工程を含むポリジメチルシランまたはポリジフェニルシランの製造方法。
- アルカリ金属およびアルカリ土類金属の失活が、界面活性剤を溶解したアルコールを用いて行われる、請求項1に記載のポリジメチルシランまたはポリジフェニルシランの製造方法。
- 界面活性剤がアニオン界面活性剤またはノニオン界面活性剤である請求項1または2に記載のポリジメチルシランまたはポリジフェニルシランの製造方法。
- 界面活性剤がノニオン界面活性剤である請求項3に記載のポリジメチルシランまたはポリジフェニルシランの製造方法。
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US12/992,775 US8829139B2 (en) | 2008-05-20 | 2009-05-15 | Process for production of polysilane compound |
JP2010513005A JP5286577B2 (ja) | 2008-05-20 | 2009-05-15 | ポリシラン化合物の製造方法 |
EP09750523.4A EP2280039B8 (en) | 2008-05-20 | 2009-05-15 | Process for production of polysilane compound |
CN200980117356.0A CN102027045B (zh) | 2008-05-20 | 2009-05-15 | 聚硅烷化合物的制备方法 |
KR1020107025379A KR101277972B1 (ko) | 2008-05-20 | 2009-05-15 | 폴리실란 화합물의 제조 방법 |
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JP2011208057A (ja) * | 2010-03-30 | 2011-10-20 | Osaka Gas Co Ltd | ポリシランの精製方法 |
WO2013133100A1 (ja) | 2012-03-07 | 2013-09-12 | 日本曹達株式会社 | ポリジアルキルシランの製造方法 |
JP2017057310A (ja) * | 2015-09-17 | 2017-03-23 | 株式会社神鋼環境ソリューション | ポリシラン製造方法 |
WO2017179369A1 (ja) * | 2016-04-11 | 2017-10-19 | 日本曹達株式会社 | 有機ポリシランの製造方法 |
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JP2011208057A (ja) * | 2010-03-30 | 2011-10-20 | Osaka Gas Co Ltd | ポリシランの精製方法 |
WO2013133100A1 (ja) | 2012-03-07 | 2013-09-12 | 日本曹達株式会社 | ポリジアルキルシランの製造方法 |
KR20140126729A (ko) | 2012-03-07 | 2014-10-31 | 닛뽕소다 가부시키가이샤 | 폴리디알킬실란의 제조 방법 |
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WO2017179369A1 (ja) * | 2016-04-11 | 2017-10-19 | 日本曹達株式会社 | 有機ポリシランの製造方法 |
US10844178B2 (en) | 2016-04-11 | 2020-11-24 | Nippon Soda Co., Ltd. | Method for producing organic polysilane |
Also Published As
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US8829139B2 (en) | 2014-09-09 |
EP2280039B1 (en) | 2013-07-31 |
JPWO2009142161A1 (ja) | 2011-09-29 |
EP2280039A1 (en) | 2011-02-02 |
EP2280039B8 (en) | 2014-01-01 |
KR101277972B1 (ko) | 2013-06-27 |
CN102027045A (zh) | 2011-04-20 |
JP5286577B2 (ja) | 2013-09-11 |
EP2280039A4 (en) | 2011-10-26 |
KR20110007183A (ko) | 2011-01-21 |
CN102027045B (zh) | 2013-01-02 |
US20110071269A1 (en) | 2011-03-24 |
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