JPH0324092A - Novel alkoxysilane compound and production thereof - Google Patents
Novel alkoxysilane compound and production thereofInfo
- Publication number
- JPH0324092A JPH0324092A JP15731989A JP15731989A JPH0324092A JP H0324092 A JPH0324092 A JP H0324092A JP 15731989 A JP15731989 A JP 15731989A JP 15731989 A JP15731989 A JP 15731989A JP H0324092 A JPH0324092 A JP H0324092A
- Authority
- JP
- Japan
- Prior art keywords
- alkoxysilane compound
- formula
- compound
- production
- reaction
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- -1 vinylsilane compound Chemical class 0.000 abstract description 6
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 2
- 239000003504 photosensitizing agent Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920000570 polyether Polymers 0.000 abstract description 2
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なアルコキシシラン化合物およびその製
造方法に関し、特に分子内に２個の活性水酸基と、ケイ
素原子に結合したアルコキシ基とを併有する新規なアル
コキシシラン化合物および該アルコキシシラン化合物を
高収率で得ることができる方法に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel alkoxysilane compound and a method for producing the same, and particularly to a novel alkoxysilane compound containing two active hydroxyl groups and an alkoxy group bonded to a silicon atom in the molecule. The present invention relates to a novel alkoxysilane compound having the present invention and a method capable of obtaining the alkoxysilane compound in high yield.
分子内に水酸基とアルコキシ基を併有するアルコキシシ
ラン化合物は、水酸基とアルコキシ基とが分子内または
分子間でエステル交換反応を起こし易いため、その合成
、単離あるいは高純度化は、非常に困難であり、稀にし
か試みられていなかった。特開昭６２−１７５４８７号
公報には、メルカプト基を有する１価のアルコール化合
物と、ケイ素原子に結合した加水分解性基を有するビニ
ルシラン化合物とを、遊離基開始剤の存在下で加熱して
反応させることによって、１分子内に１個の水酸基を有
するアルコキシシラン化合物を製造する方法が記載され
ている。Alkoxysilane compounds that have both a hydroxyl group and an alkoxy group in the molecule tend to undergo transesterification reactions between the hydroxyl group and the alkoxy group within or between molecules, making it extremely difficult to synthesize, isolate, or purify them. Yes, it was rarely attempted. JP-A-62-175487 discloses that a monohydric alcohol compound having a mercapto group and a vinylsilane compound having a hydrolyzable group bonded to a silicon atom are heated in the presence of a free radical initiator to react. A method for producing an alkoxysilane compound having one hydroxyl group in one molecule is described.
しかし、前記特開昭６２−１７５４８７号公報には、１
分子内に２個の水酸基を有するアルコキシシラン化合物
は記載されていない。However, in the above-mentioned Japanese Patent Application Laid-Open No. 175487/1987, 1
No alkoxysilane compound having two hydroxyl groups in the molecule is described.
そこで本発明の目的は、分子内に２個の水酸基とアルコ
キシ基を併有する新規なアルコキシシラン化合物および
そのアルコキシシラン化合物を高収率で製造することが
できる方法を提供することにある。Therefore, an object of the present invention is to provide a novel alkoxysilane compound having both two hydroxyl groups and an alkoxy group in the molecule, and a method for producing the alkoxysilane compound in high yield.
（課題を解決するための手段〕
本発明は、
式（Ｉ）：
〔ここで、ＲｌおよびＲ２は同一でも異なってもよく、
炭素原子数２以上のアルキル基であり、ｎはＯ〜２の整
数である〕で表される新規なアルコキシシラン化合物を
提供するものである。(Means for Solving the Problems) The present invention has the following features: Formula (I): [Here, Rl and R2 may be the same or different,
The present invention provides a novel alkoxysilane compound represented by an alkyl group having 2 or more carbon atoms, and n is an integer of O to 2.
本発明のアルコキシシラン化合物を表す前記式（１）に
おいて、Ｒ１およびＲ２が表す炭素原子数２以上のアル
キル基としては、例えば、エチル基、ｉ−プロビル基、
ｎ−プロビル基等が代表的である。ｎはＯ〜２の整数で
ある。In the above formula (1) representing the alkoxysilane compound of the present invention, examples of the alkyl group having 2 or more carbon atoms represented by R1 and R2 include an ethyl group, an i-probyl group,
A typical example is n-probyl group. n is an integer from O to 2.
本発明のアルコキシシラン化合物は、例えば、３−メル
カプト−１．２−プロパンジオールと、下記式（ＩＩ）
：
（Ｒ”）．
（Ｒ’Ｏ） ｚ−Ｉ，Ｓｔ ＣＨ＝ＣＨｚ
（ ＩＩ ）〔ここで、Ｒｌ，Ｒ２およびｎは
前記式（Ｉ）と同じである］
で表されるビニルシラン化合物とを、触媒の存在下に、
光を照射して反応させる工程を有する製造方法により製
造することができる。The alkoxysilane compound of the present invention includes, for example, 3-mercapto-1,2-propanediol and the following formula (II).
: (R"). (R'O) z-I, St CH=CHz
(II) [Here, Rl, R2 and n are the same as in the above formula (I)] A vinylsilane compound represented by
It can be manufactured by a manufacturing method that includes a step of irradiating light and causing a reaction.
用いられる触媒は光増感剤として通常用いられているも
のでよく、例えば、ペンゾフエノン、アセトーフェノン
、ジベンゾイル、ベンゾイン等が挙げられる。The catalyst used may be one commonly used as a photosensitizer, such as penzophenone, acetophenone, dibenzoyl, benzoin, and the like.
触媒の使．用量は、通常、式（ＩＩ）で表されるビニル
シラン化合物に対して０．１〜１０重量％、好ましくは
０．５〜２重量％程度でよい。The messenger of the catalyst. The dosage may be generally about 0.1 to 10% by weight, preferably about 0.5 to 2% by weight, based on the vinylsilane compound represented by formula (II).
照射する光は、紫外線が好ましい。The light to be irradiated is preferably ultraviolet light.
また、光を照射するために用いられる光源としては、高
圧水銀ランプ、低圧水銀ランプ等が挙げられ、好ましく
は高圧水銀ランプである。Further, examples of the light source used for irradiating light include a high pressure mercury lamp, a low pressure mercury lamp, etc., and preferably a high pressure mercury lamp.
反応は、反応溶媒中で行ってもよいし、溶媒を用いずに
無溶媒で行ってもよく、いずれの場合にも良好に反応を
行うことができる。用いられる反応溶媒としては、例え
ば、ヘキサン、トルエン等の炭化水素系溶媒；ジエチル
エーテル、テトラハイドロフラン等のエーテル系溶媒な
どが挙げられる。これらは、１種単独でも２種以上を混
合しても用いられる。The reaction may be carried out in a reaction solvent or in the absence of a solvent, and the reaction can be carried out satisfactorily in either case. Examples of the reaction solvent used include hydrocarbon solvents such as hexane and toluene; ether solvents such as diethyl ether and tetrahydrofuran. These may be used alone or in combination of two or more.
反応温度は、通常、−２０〜１００゜Ｃ程度である。The reaction temperature is usually about -20 to 100°C.
副生１６の生或が少ない点でＯ〜３０″Ｃが好ましい。O to 30''C is preferable since the production of by-product 16 is small.
反応の雰囲気は、乾燥した不活性雰囲気が好ましく、例
えば、窒素雰囲気である。The reaction atmosphere is preferably a dry, inert atmosphere, such as a nitrogen atmosphere.
本発明のアルコキシシラン化合物は、分子内に２一個の
水酸基を有するため、エポキシ基、カルボキシル基、イ
ソシアナート基等の水酸基と縮合可能な官能基を分子内
に複数個有する各種の単量体と重縮合させることができ
る。そのため、ポリエーテル、ポリエステル、ポリウレ
タン等の樹脂の製造に使用してこれらの樹脂の特性を改
質するのに有用である。また、本発明のアルコキシシラ
ン化合物は、水酸基と縮合可能な単量体と共縮合させる
ことにより、加水分解性を有するケイ素原子に結合した
アルコキシ基を分子内に含有するため水架橋性を有する
重合体を得るのに有用である。Since the alkoxysilane compound of the present invention has 21 hydroxyl groups in the molecule, it can be used with various monomers having multiple functional groups in the molecule that can be condensed with hydroxyl groups such as epoxy groups, carboxyl groups, and isocyanate groups. Can be polycondensed. Therefore, it is useful in the production of resins such as polyether, polyester, and polyurethane to modify the properties of these resins. In addition, the alkoxysilane compound of the present invention can be co-condensed with a monomer that can be condensed with a hydroxyl group, so that the alkoxysilane compound has a water-crosslinking property because it contains a hydrolyzable alkoxy group bonded to a silicon atom in the molecule. Useful for obtaining union.
以下、実施例を挙げて本発明を詳細に説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１
還流コンデンサー、温度計および容量２５ｍｌの滴下ロ
一トを取付け、磁気攪拌装置にセットされた内容積５０
−のガラス製反応器に、トリエトキシビニルシラン２２
．８ ｇ （０．１２ ミリモル）を仕込み、アセトフ
ェノン０．３２ ｇを加えて、攪拌しながら溶解させた
。次に、窒素雰囲気下、高圧水銀ランプ（ＩＯＯＷ）で
光を照射しながら、温度を３０゜Ｃ以下に保って、滴下
ロートから３−メルカプト−１． ２プロパンジオー
ル１０．８ ｇ （０．１０ ミリモル）を約ｌ時間掛
けて滴下して反応させた。その後、室温下に２時間熟威
させた。得られた反応混合物を、１ｍｍ｝Ｉｇの減圧下
、室温でストリップして低沸点或分を除去したところ、
無色透明な油秋物２４．９ｇを得た。Example 1 A reflux condenser, a thermometer and a dropping funnel with a capacity of 25 ml were installed, and an internal volume of 50 ml was set on a magnetic stirrer.
- In a glass reactor, triethoxyvinylsilane 22
．． 8 g (0.12 mmol) was added, and 0.32 g of acetophenone was added and dissolved with stirring. Next, under a nitrogen atmosphere, 3-mercapto-1. 10.8 g (0.10 mmol) of 2-propanediol was added dropwise over about 1 hour to cause a reaction. Thereafter, it was allowed to ripen at room temperature for 2 hours. The resulting reaction mixture was stripped at room temperature under a vacuum of 1 mm}Ig to remove some of the low boiling point.
24.9 g of colorless and transparent oil was obtained.
得られた油状物を質量分析に供し、またその３Ｃ−ＮＭ
ＲスペクトルおよびＩＲスペクトルを測定したところ、
下記の結果が得られた。The obtained oil was subjected to mass spectrometry, and its 3C-NM
When the R spectrum and IR spectrum were measured,
The following results were obtained.
ＩＲスペクトル：下記の波数に吸収ピークが認められた
。IR spectrum: Absorption peaks were observed at the following wave numbers.
３３６０ｃｍ−’，２９６０ ｃｍ−’，２８４０ ｃ
ｍ−’，１３９０ ｃｍ−’１２８０ｃｍ−’，１０７
０ ｃｍ−’，９５０ｃｍ−。3360cm-', 2960cm-', 2840c
m-', 1390 cm-'1280 cm-', 107
0 cm-', 950 cm-.
質量分析：直接導入一化学イオン化法
ｍ／Ｚ：２９９
３Ｃ−ＮＭＲスペクトル：溶媒： Ｃ，Ｏ．δ： １
２．５ｐｐｍ（Ｓｉ旦ＨｚＣｔｈ ）１８．５ｐｐｍ
（Ｃｔｌ３ＣＨｚＯ）
２７．３ｐｐｍ（ＣＩＩｚＣｌｌｚＳ）３５．６１１ｐ
ｍ（ＳＣＩＩｚＣＨ）
５８．６ｐｐｍ（ＣＩ｛ｚｃＨｚｏ）
６５． ６ｐｐｍ （Ｃｌｌ ｚＯＨ）７１．３ｐｐｍ
（ＣＨｚＣＨ（Ｏｆｔ） ）以上の結果から、下記式：
ＯＨ
（Ｃａｌｌｓ’） ａｓｉ ＣｌｈＣＨｚ Ｓ
ＣＨ２ＣＨＣＨＺ ＯＨで表される２−（２．３−ジ
ヒドロキシプロピルチオ）エチルトリエトキシシランが
得られたことがわかった。（収率： ９１．４％）
実施例２
トリエトキシビニルシランの代わりに、ジエトキシメチ
ルヒ゛ニルシラン１９．２ｇ（０．１２ ミリモル）を
、アセトフエノンの代わりにペンヅフエノン０．４７
ｇ （２．６ミリモル）を用いた以外は、実施例ｌと同
様にして油状物２７．０ｇを得、これを質量分析に供し
、またそのＩ”Ｃ−ＮＭＲスペクトルおよびＩＲスペク
トルを測定したところ、下記の結果が？られた。Mass spectrometry: Direct introduction chemical ionization m/Z: 299 3C-NMR spectrum: Solvent: C, O. δ: 1
2.5ppm (SidanHzCth) 18.5ppm
(Ctl3CHzO) 27.3ppm (CIIzCllzS) 35.611p
m(SCIIzCH) 58.6ppm(CI{zcHzo) 65. 6ppm (Cll zOH) 71.3ppm
(CHzCH(Oft)) From the above results, the following formula: OH (Calls') asi ClhCHz S
It was found that 2-(2,3-dihydroxypropylthio)ethyltriethoxysilane, represented by CH2CHCHZOH, was obtained. (Yield: 91.4%) Example 2 19.2 g (0.12 mmol) of diethoxymethylvinylsilane was used instead of triethoxyvinylsilane, and 0.47 g of penduphenone was used instead of acetophenone.
27.0 g of an oily substance was obtained in the same manner as in Example 1, except that 2.6 mmol of g (2.6 mmol) was used, and this was subjected to mass spectrometry, and its I''C-NMR spectrum and IR spectrum were measured. , the following results were obtained.
ＩＲスペクトル二下記の波数に吸収ピークが認められた
。Absorption peaks were observed at wave numbers below 2 in the IR spectrum.
３３６０ｃｍ−’，２８８０ ｃｍ−’，１３９０ ａ
ｍ−’，１２６０ ｃｍ−’１１６０ｃ＋ｒ’ １０７
０ ｃｍ−’，９４０ｃｍ−’，８００ｃｍ質量分析：
直接導入一化学イオン化法
ｍ／Ｚ：２６９
’Ｃ−ＮＭＲスペクトル：溶媒： Ｃｌ，Ｄ＆δ：
−４．５ｐｐｍ（旦ＨｚＳｉ）
１５．６ｐｐｍ（ＳｉＣＨｚ）
１８．６ｐｐｍ（ＣＨｓＣＨｚＯ）
２７．４ｐｐｍ（ＣＨｚＣＨｚＳ）
３５．６ｐｐｍ（Ｓ旦１１■Ｃｌ）
５８．３ｐｐｍ（ＣＩ，Ｃ｝！ｚ）
６５．７ｐｐｍ（ＣＨｚＯＨ）
７１．４ｐｐｍ（ＣＨ逅Ｈ（ＯＨ） ）以上の結果から
、下記式：
ＣＨ３ ０｝１
（ＣｚＨｓＯ）ｚＳｉ ＣＨｚＣＨｚ Ｓ ＣＨ
ｚＣＨＣＨｚ Ｏｆｆで表される２−（２．３−ジヒ
ドロキシブ口ビルチオ）エチルジエトキシメチルシラン
が得られたことがわかった。（収率： ９５．６％）実
施例３
トリエトキシビニルシランの代わりに、トリイソブロボ
キシビニルシラン２７．８ ｇ （０． １２ ミリモ
ル）を使用し、アセトフエノンの使用量を０．３０ ｇ
（２．５ミリモル）に変えた以外は、実施例１と同様
にして油状物３９．３ｇを得、これを質量分析に供し、
またその”Ｃ−ＮＭＲスペクトルおよびＩＲスペクトル
を測定したところ、下記の結果が得られた。3360 cm-', 2880 cm-', 1390 a
m-', 1260 cm-'1160c+r' 107
0 cm-', 940 cm-', 800 cm Mass spectrometry:
Direct introduction chemical ionization method m/Z: 269'C-NMR spectrum: Solvent: Cl, D & δ:
-4.5ppm (Si) 15.6ppm (SiCHz) 18.6ppm (CHsCHzO) 27.4ppm (CHzCHzS) 35.6ppm (Sdan11■Cl) 58.3ppm (CI, C}!z) 65.7ppm (CHzOH) 71.4ppm (CH逅H(OH) ) From the above results, the following formula: CH3 0}1 (CzHsO)zSi CHzCHz S CH
It was found that 2-(2,3-dihydroxybutybutylthio)ethyldiethoxymethylsilane, represented by zCHCHz Off, was obtained. (Yield: 95.6%) Example 3 27.8 g (0.12 mmol) of triisobroboxyvinylsilane was used instead of triethoxyvinylsilane, and the amount of acetophenone used was 0.30 g.
(2.5 mmol) was obtained in the same manner as in Example 1, and this was subjected to mass spectrometry.
Furthermore, when its C-NMR spectrum and IR spectrum were measured, the following results were obtained.
ＩＲスペクトル：下記の波数に吸収ピークが認められた
。IR spectrum: Absorption peaks were observed at the following wave numbers.
３３６０ｃｍ−’，２９６０ ｃｍ−’＋１３８０ ｃ
ｒｎ−’．１１２０ ｃｍ−’１０４０ｃｍ−’
質量分折：直接導入一花学イオン化法
ｍ／Ｚ：３４１
直ゴＣ−ＮＭＲスベクトノレ：溶媒： Ｃ６Ｄ６δ
： １４． １１）ｌ）ｍ（ＳｉＣＩＩｚＣｌｌ）２
５．７ｐｐｍ（（ＣＨ＊）ｚｃＨｏ ）２７．６ｐｐｍ
（ＣＨ２ＣＨｚＳ）
３５．７ｐｐｍ（ＳＣ！（．ＣＨ）
６５．４ｐｐｍ（（Ｃｌ：＋） ｚｃｌＩｏ）６５．
５ｐｐｍ （ＣＨ ｚＯ｝１）７１．１ｐｐｍ（ＣＨｚ
Ｃｔｌ（ＯＨ） ）以上の結果から、下記式：
キシシラン化合物を、高収率で得ることができ、工業的
実用価値が大である。3360cm-', 2960cm-'+1380c
rn-'. 1120 cm-'1040 cm-' Mass spectrometry: Direct introduction Ichikagaku ionization method m/Z: 341 Direct C-NMR spectrum: Solvent: C6D6δ
: 14. 11)l)m(SiCIIzCll)2
5.7ppm ((CH*)zcHo )27.6ppm
(CH2CHzS) 35.7ppm (SC!(.CH) 65.4ppm ((Cl:+) zclIo)65.
5ppm (CH zO}1) 71.1ppm (CH zO}1)
Ctl(OH) ) From the above results, the xysilane compound of the following formula can be obtained in high yield and has great industrial practical value.
Claims (2)
く、炭素原子数２以上のアルキ ル基であり、ｎは０〜２の整数である〕 で表されるアルコキシシラン化合物。(1) Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [Here, R^1 and R^2 may be the same or different, and are an alkyl group having 2 or more carbon atoms. , n is an integer of 0 to 2] An alkoxysilane compound represented by:
あって、３−メルカプト−１，２−プロパンジオールと
、下記式（II）： ▲数式、化学式、表等があります▼（II） 〔ここで、Ｒ＾１、Ｒ＾２およびｎは前記式（ I ）と
同じである〕 で表されるビニルシラン化合物とを、触媒の存在下に、
光を照射して反応させる工程を有する製造方法。(2) A method for producing an alkoxysilane compound according to claim 1, which comprises 3-mercapto-1,2-propanediol and the following formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) [here and R^1, R^2 and n are the same as in formula (I) above] in the presence of a catalyst,
A manufacturing method that includes a step of irradiating light and causing a reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15731989A JPH0324092A (en) | 1989-06-20 | 1989-06-20 | Novel alkoxysilane compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15731989A JPH0324092A (en) | 1989-06-20 | 1989-06-20 | Novel alkoxysilane compound and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0324092A true JPH0324092A (en) | 1991-02-01 |
Family
ID=15647095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15731989A Pending JPH0324092A (en) | 1989-06-20 | 1989-06-20 | Novel alkoxysilane compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0324092A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3388144A (en) * | 1965-07-15 | 1968-06-11 | Dow Corning | Polymercaptoorgano and polyhydroxyorgano silanes and siloxanes |
| JPS60231761A (en) * | 1984-05-01 | 1985-11-18 | Shin Etsu Chem Co Ltd | Curable silicone rubber composition |
| JPS61155390A (en) * | 1984-12-28 | 1986-07-15 | Sanwa Kagaku Kenkyusho:Kk | Novel organic silicon compound, non-toxic salt thereof, preparation thereof, and antitumor agent containing said compound as active component |
-
1989
- 1989-06-20 JP JP15731989A patent/JPH0324092A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3388144A (en) * | 1965-07-15 | 1968-06-11 | Dow Corning | Polymercaptoorgano and polyhydroxyorgano silanes and siloxanes |
| JPS60231761A (en) * | 1984-05-01 | 1985-11-18 | Shin Etsu Chem Co Ltd | Curable silicone rubber composition |
| JPS61155390A (en) * | 1984-12-28 | 1986-07-15 | Sanwa Kagaku Kenkyusho:Kk | Novel organic silicon compound, non-toxic salt thereof, preparation thereof, and antitumor agent containing said compound as active component |
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