JPH08291184A - Production of mercaptopropylsilane compound - Google Patents
Production of mercaptopropylsilane compoundInfo
- Publication number
- JPH08291184A JPH08291184A JP9711995A JP9711995A JPH08291184A JP H08291184 A JPH08291184 A JP H08291184A JP 9711995 A JP9711995 A JP 9711995A JP 9711995 A JP9711995 A JP 9711995A JP H08291184 A JPH08291184 A JP H08291184A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mercaptopropylsilane
- alkali metal
- hydrosulfide
- halogenopropylsilane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、メトキシ基またはエト
キシ基のアルコキシル基を有するメルカプトプロピルシ
ラン化合物の製造方法に関するものである。FIELD OF THE INVENTION The present invention relates to a method for producing a mercaptopropylsilane compound having an alkoxyl group such as a methoxy group or an ethoxy group.
【０００２】[0002]
【従来の技術】メルカプトプロピルシラン化合物は、カ
ップリング剤、樹脂改質剤、無機物質の表面処理剤また
はシリコーン樹脂の原料として知られている。2. Description of the Related Art Mercaptopropylsilane compounds are known as raw materials for coupling agents, resin modifiers, surface treatment agents for inorganic substances, and silicone resins.
【０００３】メルカプトプロピルシラン化合物の製造方
法として、英国特許第１１０２２５１号明細書にハロゲ
ノプロピルシラン化合物とアルカリ金属水硫化物とをア
ルコール溶媒中で反応させる方法が記載されている。As a method for producing a mercaptopropylsilane compound, British Patent No. 1102251 describes a method of reacting a halogenopropylsilane compound with an alkali metal hydrosulfide in an alcohol solvent.
【０００４】この方法において、アルカリ金属水硫化物
の量がハロゲノプロピルシラン化合物と同量程度である
と、反応時間が非常に長いだけでなく、原料のハロゲノ
プロピルシラン化合物が、目的物のメルカプトプロピル
シラン化合物と沸点が近いために反応後も残存してしま
い、その分離のために収率が著しく低下してしまう。こ
のためアルカリ金属水硫化物は、ハロゲノプロピルシラ
ン化合物に対して過剰量使用することが望ましい。In this method, when the amount of the alkali metal hydrosulfide is about the same as that of the halogenopropylsilane compound, not only the reaction time is very long, but also the starting halogenopropylsilane compound is the target mercaptopropyl compound. Since the boiling point of the silane compound is close to that of the silane compound, the silane compound remains after the reaction, and the separation thereof causes a marked decrease in yield. Therefore, it is desirable to use the alkali metal hydrosulfide in an excess amount with respect to the halogenopropylsilane compound.
【０００５】しかしながら、アルカリ金属水硫化物をハ
ロゲノプロピルシラン化合物に対して過剰量使用する
と、反応終了後に蒸留単離する際に、反応に使用されな
かったアルカリ金属水硫化物が熱不均化反応をおこして
硫化水素が発生し、それが生成したメルカプトプロピル
シラン化合物に混入して強い不快臭を発生したり、過剰
量のアルカリ金属水硫化物によるアルカリ性が原因とな
って、生成したメルカプトプロピルシラン化合物が脱ア
ルコール閉環縮合反応を起こして純度の高いメルカプト
プロピルシラン化合物が得られないことがあった。However, if the alkali metal hydrosulfide is used in an excess amount with respect to the halogenopropylsilane compound, the alkali metal hydrosulfide not used in the reaction is subjected to a heat disproportionation reaction during distillation isolation after the completion of the reaction. As a result, hydrogen sulfide is generated, which mixes with the mercaptopropylsilane compound generated to generate a strong unpleasant odor, or due to the alkalinity due to an excessive amount of alkali metal hydrosulfide, the generated mercaptopropylsilane In some cases, the compound undergoes dealcoholization ring-closure condensation reaction and a high-purity mercaptopropylsilane compound cannot be obtained.
【０００６】[0006]
【発明が解決しようとする課題】このため、ハロゲノプ
ロピルシラン化合物とアルカリ金属水硫化物とをアルコ
ール溶媒中で短時間で完全に反応させることができ、生
成したメルカプトプロピルシラン化合物を蒸留単離する
時に不快臭を発生することがなく、高収率で高純度なメ
ルカプトプロピルシラン化合物の製造方法が望まれてい
た。Therefore, the halogenopropylsilane compound and the alkali metal hydrosulfide can be completely reacted in an alcohol solvent in a short time, and the produced mercaptopropylsilane compound is isolated by distillation. A method for producing a high-purity, high-purity mercaptopropylsilane compound without causing an unpleasant odor at times has been desired.
【０００７】本発明は前記の課題を解決するためなされ
たもので、ハロゲノプロピルシラン化合物とアルカリ金
属水硫化物とをアルコール溶媒中で短時間で完全に反応
させることができ、生成したメルカプトプロピルシラン
化合物を蒸留単離する時に硫化水素が発生、混入して不
快臭を発生することがなく、生成したメルカプトプロピ
ルシラン化合物が閉環縮合物を副生することがなく、高
収率で高純度なメルカプトプロピルシラン化合物の製造
方法を提供することを目的とする。The present invention has been made to solve the above-mentioned problems, and a halogenopropylsilane compound and an alkali metal hydrosulfide can be completely reacted in an alcohol solvent in a short time, and the produced mercaptopropylsilane. Hydrogen sulfide is not generated or mixed when distilling and isolating the compound, and no unpleasant odor is generated, and the generated mercaptopropylsilane compound does not form a ring-closing condensation product as a by-product, and high-purity mercapto It is an object to provide a method for producing a propylsilane compound.
【０００８】[0008]
【課題を解決するための手段】前記の目的を達成するた
めになされた本発明のメルカプトプロピルシラン化合物
の製造方法は、アルカリ金属水硫化物のアルコール溶液
に、下記式〔I〕 Ｘ−(ＣＨ2)3−Ｓｉ(ＣＨ3)n(ＯＲ)3-n 〔I〕 で表されるハロゲノプロピルシラン化合物を加えて反応
させた後、酸を加えて濾過し、濾液を蒸留単離して下記
式〔II〕 ＨＳ−(ＣＨ2)3−Ｓｉ(ＣＨ3)n(ＯＲ)3-n 〔II〕 （〔I〕、〔II〕式中のＸは塩素原子または臭素原子、
Ｒはメチル基またはエチル基、ｎは０〜２の整数）で表
される３−メルカプトプロピルトリメトキシシラン、３
−メルカプトプロピルトリエトキシシラン、３−メルカ
プトプロピルメチルジメトキシシラン、３−メルカプト
プロピルメチルジエトキシシラン、３−メルカプトプロ
ピルジメチルメトキシシラン、または３−メルカプトプ
ロピルジメチルエトキシシランのメルカプトプロピルシ
ラン化合物を得る方法である。The method for producing a mercaptopropylsilane compound of the present invention, which was made in order to achieve the above object, comprises the following formula [I] X- (CH) in an alcohol solution of an alkali metal hydrosulfide. 2 ) 3- Si (CH 3 ) n (OR) 3-n [I] After reacting with a halogenopropylsilane compound represented by the formula [I], an acid is added and filtered. [II] HS- (CH 2) 3 -Si ( CH 3) n (oR) 3-n [II] ([I], [II] X in the formula is a chlorine atom or a bromine atom,
R is a methyl group or an ethyl group, n is an integer of 0 to 2), 3-mercaptopropyltrimethoxysilane, 3
-A method for obtaining a mercaptopropylsilane compound of mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropylmethyldiethoxysilane, 3-mercaptopropyldimethylmethoxysilane, or 3-mercaptopropyldimethylethoxysilane. .
【０００９】前記酸は水溶液でない酸、例えば蟻酸、酢
酸、プロピオン酸、シュウ酸、マロン酸、コハク酸等の
有機酸、または塩化水素、臭化水素、ヨウ化水素、リン
酸、ほう酸等の無機酸であれば何でも良く、中でも価
格、扱い易さの面から酢酸または塩化水素が好ましい。
塩酸等の水溶液の酸を使用すると、生成したメルカプト
プロピルシラン化合物が加水分解縮合物を副生してしま
う。The acid is not an aqueous solution, for example, organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, malonic acid and succinic acid, or inorganic acids such as hydrogen chloride, hydrogen bromide, hydrogen iodide, phosphoric acid and boric acid. Any acid may be used, and acetic acid or hydrogen chloride is preferred from the viewpoints of price and ease of handling.
When an acid of an aqueous solution such as hydrochloric acid is used, the produced mercaptopropylsilane compound produces a hydrolysis-condensation product as a by-product.
【００１０】前記アルカリ金属水硫化物は、水硫化リチ
ウム、水硫化ナトリウムまたは水硫化カリウムが挙げら
れる。Examples of the alkali metal hydrosulfide include lithium hydrosulfide, sodium hydrosulfide and potassium hydrosulfide.
【００１１】前記ハロゲノプロピルシラン化合物は、具
体的には３−クロロプロピルトリメトキシシラン、３−
クロロプロピルトリエトキシシラン、３−クロロプロピ
ルメチルジメトキシシラン、３−クロロプロピルメチル
ジエトキシシラン、３−クロロプロピルジメチルメトキ
シシラン、３−クロロプトプロピルジメチルエトキシシ
ラン、３−ブロモプロピルトリメトキシシラン、３−ブ
ロモプロピルトリエトキシシラン、３−ブロモプロピル
メチルジメトキシシラン、３−ブロモプロピルメチルジ
エトキシシラン、３−ブロモプロピルジメチルメトキシ
シラン、または３−ブロモプロピルジメチルエトキシシ
ランである。The halogenopropylsilane compound is specifically 3-chloropropyltrimethoxysilane or 3-chloropropyltrimethoxysilane.
Chloropropyltriethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropylmethyldiethoxysilane, 3-chloropropyldimethylmethoxysilane, 3-chloroputpropyldimethylethoxysilane, 3-bromopropyltrimethoxysilane, 3- It is bromopropyltriethoxysilane, 3-bromopropylmethyldimethoxysilane, 3-bromopropylmethyldiethoxysilane, 3-bromopropyldimethylmethoxysilane, or 3-bromopropyldimethylethoxysilane.
【００１２】使用する酸の量は、アルカリ金属水硫化物
と同量程度が好ましいが、同量以下または同量以上でも
無添加の場合に比較して良好な結果が得られる。The amount of the acid used is preferably the same as that of the alkali metal hydrosulfide, but even if the amount is equal to or less than or equal to the same amount, good results can be obtained as compared with the case of no addition.
【００１３】[0013]
【発明の効果】本発明の方法でメルカプトプロピルシラ
ン化合物を製造すると、ハロゲノプロピルシラン化合物
とアルカリ金属水硫化物とをアルコール溶媒中で短時間
で完全に反応させることができ、生成したメルカプトプ
ロピルシラン化合物を蒸留単離する時に硫化水素が発
生、混入して不快臭を発生することがなく、生成したメ
ルカプトプロピルシラン化合物が閉環縮合物を副生する
ことがなく、高収率で高純度なメルカプトプロピルシラ
ン化合物を得ることができる。When the mercaptopropylsilane compound is produced by the method of the present invention, the halogenopropylsilane compound and the alkali metal hydrosulfide can be completely reacted in an alcohol solvent in a short time, and the produced mercaptopropylsilane is produced. Hydrogen sulfide is not generated or mixed when distilling and isolating the compound, and no unpleasant odor is generated, and the generated mercaptopropylsilane compound does not form a ring-closing condensation product as a by-product, and high-purity mercapto A propylsilane compound can be obtained.
【００１４】[0014]
【実施例】以下、本発明の実施例を詳細に説明する。EXAMPLES Examples of the present invention will be described in detail below.
【００１５】実施例１ ナトリウムメトキシドの濃度２８重量％メタノール溶液
３４７．２ｇ（ナトリウムメトキシド：１．８ｍｏｌ）
を２リットルのオートクレーブに仕込み、密閉して室温
下で硫化水素６３．１ｇ（１．８５ｍｏｌ）を吹き込み
水硫化ナトリウムのメタノール溶液を得た。この溶液に
密閉したオートクレーブ中７０℃下で、３−クロロプロ
ピルトリメトキシシラン２９８．１ｇ（１．５０ｍｏ
ｌ）を２時間かけて加えた後、７０℃下で４時間静置し
て反応を完結させた。Example 1 Concentration of sodium methoxide 28% by weight methanol solution 347.2 g (sodium methoxide: 1.8 mol)
Was charged into a 2 liter autoclave, sealed, and 63.1 g (1.85 mol) of hydrogen sulfide was blown at room temperature to obtain a solution of sodium hydrosulfide in methanol. At 70 ° C. in an autoclave sealed with this solution, 298.1 g (1.50 mo of 3-chloropropyltrimethoxysilane)
l) was added over 2 hours, and then the mixture was allowed to stand at 70 ° C. for 4 hours to complete the reaction.
【００１６】この反応液に、室温下で酢酸１８．０ｇ
（０．３ｍｏｌ）を加えた後、濾過して塩を除去し、濾
液を減圧下で蒸留して８１〜８２℃／６ｍｍＨｇの留分
を分取することにより、３−メルカプトプロピルトリメ
トキシシラン２３８．４ｇ（収率８１％）を得た。得ら
れた３−メルカプトプロピルトリメトキシシランの純度
をガスクロマトグラフィーで調べたところ９９％であっ
た。また硫化水素臭は全くなかった。18.0 g of acetic acid was added to this reaction solution at room temperature.
After adding (0.3 mol), the salt is removed by filtration, the filtrate is distilled under reduced pressure, and a fraction of 81 to 82 ° C./6 mmHg is collected to give 3-mercaptopropyltrimethoxysilane 238. 0.4 g (yield 81%) was obtained. When the purity of the obtained 3-mercaptopropyltrimethoxysilane was examined by gas chromatography, it was 99%. There was no hydrogen sulfide odor at all.
【００１７】比較例１ 酢酸を加えないことを除き実施例１と同様にして３−メ
ルカプトプロピルトリメトキシシラン２２７．５ｇ（収
率７７．２％）を得た。得られた３−メルカプトプロピ
ルトリメトキシシランの純度をガスクロマトグラフィー
で調べたところ脱メタノール閉環縮合化合物が４．６％
含まれていた。また強い硫化水素臭を発していた。Comparative Example 1 227.5 g (yield: 77.2%) of 3-mercaptopropyltrimethoxysilane was obtained in the same manner as in Example 1 except that acetic acid was not added. When the purity of the obtained 3-mercaptopropyltrimethoxysilane was examined by gas chromatography, 4.6% of the demethanol ring-closing condensed compound was obtained.
Was included. It also emitted a strong hydrogen sulfide odor.
【００１８】実施例２ ナトリウムメトキシドの濃度２８重量％メタノール溶液
４０５．０ｇ（ナトリウムメトキシド：２．１ｍｏｌ）
を２リットルのオートクレーブに仕込み、密閉して室温
下で硫化水素７３．０ｇ（２．１４ｍｏｌ）を吹き込み
水硫化ナトリウムのメタノール溶液を得た。この溶液に
密閉したオートクレーブ中７０℃下で、３−クロロプロ
ピルトリメトキシシラン２９８．１ｇ（１．５０ｍｏ
ｌ）を２時間かけて加えた後、１００℃下で２時間静置
して反応を完結させた。Example 2 405.0 g of a 28% by weight sodium methoxide methanol solution (sodium methoxide: 2.1 mol)
Was charged into a 2 liter autoclave, sealed, and hydrogen sulfide (73.0 g, 2.14 mol) was blown at room temperature to obtain a solution of sodium hydrosulfide in methanol. At 70 ° C. in an autoclave sealed with this solution, 298.1 g (1.50 mo of 3-chloropropyltrimethoxysilane)
l) was added over 2 hours, and then the mixture was allowed to stand at 100 ° C. for 2 hours to complete the reaction.
【００１９】この反応液に、室温下で塩化水素３．６ｇ
（０．１ｍｏｌ）を加えた後、濾過して塩を除去し、濾
液を減圧下で蒸留して８１〜８２℃／６ｍｍＨｇの留分
を分取することにより、３−メルカプトプロピルトリメ
トキシシラン３２８．１ｇ（収率８４％）を得た。得ら
れた３−メルカプトプロピルトリメトキシシランの純度
をガスクロマトグラフィーで調べたところ９９％であっ
た。また硫化水素臭は全くなかった。3.6 g of hydrogen chloride was added to this reaction solution at room temperature.
(0.1 mol) was added, followed by filtration to remove salts, and the filtrate was distilled under reduced pressure to separate a fraction of 81 to 82 ° C / 6 mmHg to give 3-mercaptopropyltrimethoxysilane 328. 0.1 g (84% yield) was obtained. When the purity of the obtained 3-mercaptopropyltrimethoxysilane was examined by gas chromatography, it was 99%. There was no hydrogen sulfide odor at all.
【００２０】実施例３ ３−クロロプロピルトリメトキシシラン２９８．１ｇ
（１．５０ｍｏｌ）の代わりに３−クロロプロピルメチ
ルジメトキシシラン２７４．１ｇ（１．５０ｍｏｌ）を
使用し、８１〜８２℃／１５ｍｍＨｇの留分を分取した
ことを除き実施例１と同様にして３−メルカプトプロピ
ルメチルジメトキシシラン２１３．７ｇ（収率７９％）
を得た。得られた３−メルカプトプロピルメチルジメト
キシシランの純度をガスクロマトグラフィーで調べたと
ころ９９％であった。また硫化水素臭は全くなかった。Example 3 298.1 g of 3-chloropropyltrimethoxysilane
In the same manner as in Example 1 except that 274.1 g (1.50 mol) of 3-chloropropylmethyldimethoxysilane was used instead of (1.50 mol) and a fraction of 81 to 82 ° C./15 mmHg was fractionated. 213.7 g of 3-mercaptopropylmethyldimethoxysilane (79% yield)
I got When the purity of the obtained 3-mercaptopropylmethyldimethoxysilane was examined by gas chromatography, it was 99%. There was no hydrogen sulfide odor at all.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 遠藤 幹夫 新潟県中頸城郡頸城村大字西福島28番地の １ 信越化学工業株式会社合成技術研究所 内 (72)発明者 山本 昭 群馬県碓氷郡松井田町大字人見１番地10 信越化学工業株式会社シリコーン電子材料 技術研究所内 (72)発明者 工藤 宗夫 群馬県碓氷郡松井田町大字人見１番地10 信越化学工業株式会社シリコーン電子材料 技術研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Mikio Endo 28, Nishi-Fukushima, Kubiki-mura, Nakabuki-gun, Niigata Prefecture 1 Synthetic Technology Laboratory, Shin-Etsu Chemical Co., Ltd. (72) Inventor Akira Yamamoto Matsui Usui-gun Gunma Prefecture Tamachi Daiji Hitomi 1-10 Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (72) Inventor Muneo Kudo Matsuida-machi, Usui-gun Gunma 1-ji Hitomi 1 Shin-Etsu Chemical Industrial Silicone Electronic Materials Research Center
Claims (2)
に、下記式〔I〕 Ｘ−(ＣＨ2)3−Ｓｉ(ＣＨ3)n(ＯＲ)3-n 〔I〕 で表されるハロゲノプロピルシラン化合物を加えて反応
させた後、酸を加えて濾過し、濾液を蒸留単離すること
を特徴とする下記式〔II〕 ＨＳ−(ＣＨ2)3−Ｓｉ(ＣＨ3)n(ＯＲ)3-n 〔II〕 （〔I〕、〔II〕式中のＸは塩素原子または臭素原子、
Ｒはメチル基またはエチル基、ｎは０〜２の整数）で表
されるメルカプトプロピルシラン化合物の製造方法。1. A halogenopropylsilane represented by the following formula [I] X- (CH 2 ) 3- Si (CH 3 ) n (OR) 3-n [I] in an alcohol solution of an alkali metal hydrosulfide. after reacting by adding a compound, it was filtered by adding an acid, the following formula, which comprises distilling isolating the filtrate (II) HS- (CH 2) 3 -Si ( CH 3) n (OR) 3 -n [II] (X in the formulas [I] and [II] is a chlorine atom or a bromine atom,
R is a methyl group or an ethyl group, and n is an integer of 0 to 2.) A method for producing a mercaptopropylsilane compound.
ウム、水硫化ナトリウムまたは水硫化カリウム、前記酸
が酢酸または塩化水素であることを特徴とする請求項１
に記載のメルカプトプロピルシラン化合物の製造方法。2. The alkali metal hydrosulfide is lithium hydrosulfide, sodium hydrosulfide or potassium hydrosulfide, and the acid is acetic acid or hydrogen chloride.
The method for producing the mercaptopropylsilane compound according to 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07097119A JP3091993B2 (en) | 1995-04-21 | 1995-04-21 | Method for producing mercaptopropylsilane compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07097119A JP3091993B2 (en) | 1995-04-21 | 1995-04-21 | Method for producing mercaptopropylsilane compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08291184A true JPH08291184A (en) | 1996-11-05 |
| JP3091993B2 JP3091993B2 (en) | 2000-09-25 |
Family
ID=14183690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07097119A Expired - Fee Related JP3091993B2 (en) | 1995-04-21 | 1995-04-21 | Method for producing mercaptopropylsilane compound |
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| JP (1) | JP3091993B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002255976A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Process for producing silicon compound bearing mercapto group |
| JP2002255978A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Method for producing silicon compound bearing mercapto group |
| JP2002255977A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Method for recovering and recycling solvent in the production of silicon compound bearing hydrolyzable group |
| US7462221B2 (en) | 2004-06-25 | 2008-12-09 | Evonik Degussa Gmbh | Process and device for the extraction of substances from silane-modified fillers |
| US7518009B2 (en) | 2005-05-03 | 2009-04-14 | Evonik Degussa Gmbh | Process for preparing mercaptoorganyl (alkoxysilanes) |
| JP2009519287A (en) * | 2005-12-16 | 2009-05-14 | エボニック デグサ ゲーエムベーハー | Method for producing (mercaptoorganyl) alkyl polyether silane |
| US7705076B2 (en) | 2006-06-09 | 2010-04-27 | Evonik Degussa Gmbh | Rubber mixtures |
| US7777063B2 (en) | 2005-08-17 | 2010-08-17 | Evonik Degussa Gmbh | Organosilicon compounds their preparation and their use |
| JP2013108024A (en) * | 2011-11-24 | 2013-06-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition for sealing and electronic component device |
| JP2015218169A (en) * | 2014-05-15 | 2015-12-07 | エボニック インダストリーズ アクチエンゲゼルシャフトＥｖｏｎｉｋ Ｉｎｄｕｓｔｒｉｅｓ ＡＧ | Manufacturing method of urea-containing mercaptosilane |
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| KR102473427B1 (en) | 2020-11-09 | 2022-12-05 | 고진희 | Wall mounting apparatus for shelves |
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1995
- 1995-04-21 JP JP07097119A patent/JP3091993B2/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4574875B2 (en) * | 2001-02-27 | 2010-11-04 | 日本曹達株式会社 | A solvent recovery and regeneration method for producing a silicon compound having a hydrolyzable group. |
| JP2002255978A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Method for producing silicon compound bearing mercapto group |
| JP2002255977A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Method for recovering and recycling solvent in the production of silicon compound bearing hydrolyzable group |
| JP2002255976A (en) * | 2001-02-27 | 2002-09-11 | Nippon Soda Co Ltd | Process for producing silicon compound bearing mercapto group |
| JP4574034B2 (en) * | 2001-02-27 | 2010-11-04 | 日本曹達株式会社 | Method for producing silicon compound having mercapto group |
| JP4574876B2 (en) * | 2001-02-27 | 2010-11-04 | 日本曹達株式会社 | Method for producing silicon compound having mercapto group |
| US7462221B2 (en) | 2004-06-25 | 2008-12-09 | Evonik Degussa Gmbh | Process and device for the extraction of substances from silane-modified fillers |
| US7518009B2 (en) | 2005-05-03 | 2009-04-14 | Evonik Degussa Gmbh | Process for preparing mercaptoorganyl (alkoxysilanes) |
| US7777063B2 (en) | 2005-08-17 | 2010-08-17 | Evonik Degussa Gmbh | Organosilicon compounds their preparation and their use |
| US7799938B2 (en) | 2005-12-16 | 2010-09-21 | Evonik Degussa Gmbh | Method for the production of (mercaptoorganyl)alkyl polyether silanes |
| JP2009519287A (en) * | 2005-12-16 | 2009-05-14 | エボニック デグサ ゲーエムベーハー | Method for producing (mercaptoorganyl) alkyl polyether silane |
| US7705076B2 (en) | 2006-06-09 | 2010-04-27 | Evonik Degussa Gmbh | Rubber mixtures |
| JP2013108024A (en) * | 2011-11-24 | 2013-06-06 | Sumitomo Bakelite Co Ltd | Epoxy resin composition for sealing and electronic component device |
| JP2015218169A (en) * | 2014-05-15 | 2015-12-07 | エボニック インダストリーズ アクチエンゲゼルシャフトＥｖｏｎｉｋ Ｉｎｄｕｓｔｒｉｅｓ ＡＧ | Manufacturing method of urea-containing mercaptosilane |
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