JPH0317169A - Silicon fluoride compound - Google Patents
Silicon fluoride compoundInfo
- Publication number
- JPH0317169A JPH0317169A JP1150536A JP15053689A JPH0317169A JP H0317169 A JPH0317169 A JP H0317169A JP 1150536 A JP1150536 A JP 1150536A JP 15053689 A JP15053689 A JP 15053689A JP H0317169 A JPH0317169 A JP H0317169A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylate
- formula
- silicon
- fluoride compound
- 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
- -1 Silicon fluoride compound Chemical class 0.000 title description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 229910052697 platinum Inorganic materials 0.000 abstract description 3
- 229910052710 silicon Inorganic materials 0.000 abstract description 3
- 239000010703 silicon Substances 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 239000011737 fluorine Substances 0.000 abstract description 2
- 229920001002 functional polymer Polymers 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000005048 methyldichlorosilane Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XNAFLNBULDHNJS-UHFFFAOYSA-N dichloro(phenyl)silicon Chemical compound Cl[Si](Cl)C1=CC=CC=C1 XNAFLNBULDHNJS-UHFFFAOYSA-N 0.000 description 1
- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical group C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は新規なフツ化ケイ素化合物に関し、特にフッ素
・ケイ素含有機能性ボリマー等の合成に有用なフン化ケ
イ素化合物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel silicon fluoride compound, and particularly to a silicon fluoride compound useful for the synthesis of fluorine/silicon-containing functional polymers.
本発明のフツ化ケイ素化合物は一般式 で表わされるフン化ケイ素化合物にある。 The silicon fluoride compound of the present invention has the general formula It is a fluorinated silicon compound represented by
このフフ化ケイ素化合物の合成は下記の反応式に示すよ
うにフツ化アルキル（メタ）アクリレートとヒドロシラ
ンを白金系触媒存在下にヒドロシリル化することによシ
行なうことができる。The fluorinated silicon compound can be synthesized by hydrosilylating a fluorinated alkyl (meth)acrylate and hydrosilane in the presence of a platinum catalyst as shown in the reaction formula below.
白金系触媒
出発原科として用いるフン化アルキル（メタ）アクリレ
ートの具体例としては、２，２．２ − ｝リフルオロ
エチル（メタ）アク’） Ｌ／−｝、２，２，５．３−
テトラフルオログロビル（メタ）アクリレート、２．２
，５，５．５−ペンタフルオログロビル（メタ）アクリ
レート、２−トリフルオロメチル−３．３．３−トリフ
ルオログロビル（メタ）アクリレー｝，２−｝リフルオ
ロメチル−２．５，５．５−テトラフルオロブロビル（
メタ）アクリレート、２，２，５，４，４．４−へキサ
フルオロブチル（メタ冫アクリレート、１−メチル−２
．２，５，４，４，４−へキサフルオロブチル（メタ）
アクリレート、１ ，１ ，２．２−テトラハイドロバ
ーフルオロデシル（メタ）アクリレー｝、１，１，２．
２−テトラハイドロ−？一トリフルオロメチルパー７ル
オロデシル（メタ）アクリレー｝、１．１−ジハイドロ
バ−フルオロプチル（メタ）アクリレート、１，１−ジ
メチル−２．２，３，３，４，４，５．５−オクタフル
オロベンチル（メタ）アクリレート、１，１−ジメチル
−２．２，５，４，４．４−へキサフルオロブチル（メ
タ）アクリレート等、等を挙げることができる。Specific examples of fluorinated alkyl (meth)acrylates used as starting materials for platinum-based catalysts include 2,2.2-}lifluoroethyl(meth)ac') L/-}, 2,2,5.3-
Tetrafluoroglovir (meth)acrylate, 2.2
, 5,5.5-pentafluoroglovir (meth)acrylate, 2-trifluoromethyl-3.3.3-trifluoroglovir (meth)acrylate},2-}lifluoromethyl-2.5,5 .5-tetrafluorobrovir (
meth)acrylate, 2,2,5,4,4,4-hexafluorobutyl(meth)acrylate, 1-methyl-2
．． 2,5,4,4,4-hexafluorobutyl (meth)
acrylate, 1,1,2.2-tetrahydroverfluorodecyl(meth)acrylate}, 1,1,2.
2-tetrahydro-? monotrifluoromethylper7fluorodecyl (meth)acrylate}, 1,1-dihydroba-fluoroptyl (meth)acrylate, 1,1-dimethyl-2.2,3,3,4,4,5.5-octafluoro Bentyl (meth)acrylate, 1,1-dimethyl-2.2,5,4,4.4-hexafluorobutyl (meth)acrylate, etc. can be mentioned.
また他の出発原料であるヒドロシランの具体例としては
、メチルジクロロシラン、メチルジエトキシシラン、メ
チルジメトキシシラン、フエニルジクロロシラン、トリ
クロロシラン、トリエトキシシラン等が代表ψ１］とし
て挙げられる。Further, specific examples of hydrosilane which is another starting material include methyldichlorosilane, methyldiethoxysilane, methyldimethoxysilane, phenyldichlorosilane, trichlorosilane, triethoxysilane and the like.
本発明の７ツ化・ケイ素化合物はカブリンク剤として或
いはシリル基を縮合せしめたフツ化シリコンゴムの原料
として、更には本発明の化合物に（メタ冫アクリロイル
基を導入し新規な重合性７ツ化ケイ素化合物製造用原科
として利用するここができる。The 7-silicone compound of the present invention can be used as a fog linking agent or as a raw material for fluorinated silicone rubber condensed with silyl groups. This can be used as a raw material for the production of silicon oxide compounds.
以下実施例によう本発明を更に詳釈に説明する。The present invention will be explained in more detail with reference to Examples below.
実施例１
冷却管を備えた二口フラスコをＮ２ で置換した。そ
こへ２．２．２ − トＩＪフルオロエチルメタクリレ
ート２０ｇ（１１９ｍｕｘｏ／） とメチルジクロロシ
ラン１ ６．４ ＆ （ １ ４ ３ ｍ １１０／
） 、及び塩化白金酸の１０％イングロビルアルコール
溶液０．１一を加えＳａＣに加熱した。約２時間加熱攪
拌後冷却し反応溶液を減圧蒸留した。得られた反応生成
物は沸点が９４〜９ ５ Ｃ／ １ ０ １１ＢＨ＆な
る特性を備えたものであシ、収量は２１．５２（収率６
５％）であった。Example 1 A two-necked flask equipped with a condenser was purged with N2. Thereto 20 g (119muxo/) of 2.2.2-tIJ fluoroethyl methacrylate and 16.4 & (143 m 110/) of methyldichlorosilane
), and 0.1 l of a 10% inglobil alcohol solution of chloroplatinic acid were added and heated to SaC. After heating and stirring for about 2 hours, the mixture was cooled and the reaction solution was distilled under reduced pressure. The obtained reaction product had a boiling point of 94 to 95C/1011BH&, and the yield was 21.52 (yield 6
5%).
得られた反応生底物についてのガスマススペクトル、元
素分析，ＩＲスペクトル、及びＮＭＲスペクトルの測定
結果から、この化合物は次式第 １ 表
Ｃ／ Ｏ
で表わされる７ツ化ケイ素化合物であることが確認され
た。このものの物性及び分析値を第１表に、ＩＲスペク
トル及びＮＭＲスペクトルを第１図及び第２図に示した
。From the measurement results of the gas mass spectrum, elemental analysis, IR spectrum, and NMR spectrum of the obtained reaction biomass, it was confirmed that this compound is a silicon heptadide compound represented by the following formula (Table 1): C/O It was done. The physical properties and analytical values of this product are shown in Table 1, and the IR spectrum and NMR spectrum are shown in Figures 1 and 2.
Claims (1)
基をＲ＾２は水素原子またはメチル基、Ｒｆは炭素数２
〜１２のフルオロアルキル基、Ｘはハロゲン原子または
アルコキシル基、 ｎは１〜３の整数を示す） で表わされるフッ化ケイ素化合物。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. Number 2
-12 fluoroalkyl groups, X is a halogen atom or an alkoxyl group, and n is an integer of 1 to 3).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1150536A JPH0317169A (en) | 1989-06-15 | 1989-06-15 | Silicon fluoride compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1150536A JPH0317169A (en) | 1989-06-15 | 1989-06-15 | Silicon fluoride compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0317169A true JPH0317169A (en) | 1991-01-25 |
Family
ID=15499016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1150536A Pending JPH0317169A (en) | 1989-06-15 | 1989-06-15 | Silicon fluoride compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0317169A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5295472A (en) * | 1992-01-06 | 1994-03-22 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting malfunction in evaporated fuel purge system used in internal combustion engine |
| US5333589A (en) * | 1991-06-10 | 1994-08-02 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting malfunction in evaporated fuel purge system |
| US5363828A (en) * | 1992-07-22 | 1994-11-15 | Aisan Kogyo Kabushiki Kaisha | Fuel vapor processing apparatus of internal combustion engine |
| US5425344A (en) * | 1992-01-21 | 1995-06-20 | Toyota Jidosha Kabushiki Kaisha | Diagnostic apparatus for evaporative fuel purge system |
| US5443051A (en) * | 1993-02-26 | 1995-08-22 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting a malfunction in an evaporated fuel purge system |
| KR100287439B1 (en) * | 1990-02-26 | 2001-08-07 | 오카메 히로무 | Self-diagnosis apparatus in a system for prevention of scat tering of fuel evaporation gas |
| WO2013082989A1 (en) * | 2011-12-08 | 2013-06-13 | Dow Corning (China) Holding Co., Ltd. | Method for the adhesion of a layer of fluorosilicone rubber to a layer of silicone rubber |
-
1989
- 1989-06-15 JP JP1150536A patent/JPH0317169A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100287439B1 (en) * | 1990-02-26 | 2001-08-07 | 오카메 히로무 | Self-diagnosis apparatus in a system for prevention of scat tering of fuel evaporation gas |
| US5333589A (en) * | 1991-06-10 | 1994-08-02 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting malfunction in evaporated fuel purge system |
| US5295472A (en) * | 1992-01-06 | 1994-03-22 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting malfunction in evaporated fuel purge system used in internal combustion engine |
| US5425344A (en) * | 1992-01-21 | 1995-06-20 | Toyota Jidosha Kabushiki Kaisha | Diagnostic apparatus for evaporative fuel purge system |
| US5363828A (en) * | 1992-07-22 | 1994-11-15 | Aisan Kogyo Kabushiki Kaisha | Fuel vapor processing apparatus of internal combustion engine |
| US5443051A (en) * | 1993-02-26 | 1995-08-22 | Toyota Jidosha Kabushiki Kaisha | Apparatus for detecting a malfunction in an evaporated fuel purge system |
| WO2013082989A1 (en) * | 2011-12-08 | 2013-06-13 | Dow Corning (China) Holding Co., Ltd. | Method for the adhesion of a layer of fluorosilicone rubber to a layer of silicone rubber |
| US9908308B2 (en) | 2011-12-08 | 2018-03-06 | Dow Corning (China) Holding Co., Ltd. | Method for the adhesion of a layer of fluorosilicone rubber to a layer of silicone rubber |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3414134B2 (en) | N, N-bis (trimethylsilyl) aminopropylsilane compound and method for producing the same | |
| JPH0572397B2 (en) | ||
| JPS61263986A (en) | Organic silicon compound | |
| JPH0317169A (en) | Silicon fluoride compound | |
| JPS609759B2 (en) | hydroalkenyloxysilane | |
| JPH0371436B2 (en) | ||
| JPH01305094A (en) | Omega-silylalkynylsilane compound and production thereof | |
| EP0459802B1 (en) | Alkoxysilanes | |
| EP0545702B1 (en) | 2-Trimethoxysilylpropionate | |
| JPH0311083A (en) | Silylating agent | |
| JPH0517487A (en) | New silane compound and its production | |
| JPH0813821B2 (en) | Vinylsilane compound | |
| JP3915883B2 (en) | Organosilicon compound | |
| US5627251A (en) | Organosilicon compound and process for its production | |
| JP3563811B2 (en) | Polyfluoroaralkylsilane derivative and method for producing the same | |
| JPS62283981A (en) | Production of organooxychlorosilane | |
| US5049688A (en) | Allyl cyclosilalactams | |
| JPS61221191A (en) | Chlorosilane compound | |
| JP2811143B2 (en) | Fluorine-containing organosilicon compound | |
| JP2980250B2 (en) | Method for producing 3- (2-oxo-1-pyrrolidinyl) propylsilane compound | |
| JP3592534B2 (en) | Organic silicon compounds | |
| JPH01316388A (en) | Polymerizable silane compound | |
| JPH0466588A (en) | Production of thexyltrichlorosilane | |
| JPH06329683A (en) | 4-tert-butylcyclohexyl group-containing silane compound | |
| JPS63241033A (en) | Vinyl group-containing polyorganosiloxane compound |