JPH0459784A - Fluorine-containing organic silicon compound - Google Patents
Fluorine-containing organic silicon compoundInfo
- Publication number
- JPH0459784A JPH0459784A JP2171564A JP17156490A JPH0459784A JP H0459784 A JPH0459784 A JP H0459784A JP 2171564 A JP2171564 A JP 2171564A JP 17156490 A JP17156490 A JP 17156490A JP H0459784 A JPH0459784 A JP H0459784A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- fluorine
- group
- groups
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 15
- 239000011737 fluorine Substances 0.000 title claims abstract description 15
- 150000003377 silicon compounds Chemical class 0.000 title description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 6
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 abstract description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 238000007259 addition reaction Methods 0.000 abstract description 3
- 239000006082 mold release agent Substances 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 2
- 238000005336 cracking Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- -1 Polysiloxane Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、文献未載の新規な含フツ素有機ケイ素化合物
に関するものである。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a novel fluorine-containing organosilicon compound that has not been described in any literature.
（従来技術）
フッ素原子を分子中に有するポリシロキサンは、耐溶剤
性、耐薬品性に優れたゴム材料用の素材として有用であ
り、また離型剤、撥水撥油剤等に使用できる素材として
有用であることが知られている。(Prior art) Polysiloxane, which has fluorine atoms in its molecules, is useful as a material for rubber materials with excellent solvent and chemical resistance, and can also be used as a material for mold release agents, water and oil repellents, etc. Known to be useful.
（発明が解決しようとするｔＪＨ）
従って本発明は、特に上記の様なフッ素含有ポリシロキ
サンの製造用原料として有用な新規なフッ素含有有機ケ
イ素化合物を提供することを目的とするものである。(tJH to be Solved by the Invention) Therefore, the object of the present invention is to provide a novel fluorine-containing organosilicon compound that is particularly useful as a raw material for producing the above-mentioned fluorine-containing polysiloxane.
（課題を達成するための手段）
本発明のフッ素含有有機ケイ素化合物は、下記一般式［
１）、
式中、
Ｒは、炭素原子数１〜８の一価炭化水素基であリ、２個
のＲは互いに同一でも異なっていてもよく、
Ｒｆハ、炭素原子数１〜１０のパーフルオロアルキル基
である、
で表わされる。かかる一般式（１）から理解される様に
、本発明のフッ素含有有機ケイ素化合物は、文献載の新
規な化合物である。(Means for achieving the object) The fluorine-containing organosilicon compound of the present invention has the following general formula [
1), in the formula, R is a monovalent hydrocarbon group having 1 to 8 carbon atoms, the two Rs may be the same or different from each other, and Rf is a group having 1 to 10 carbon atoms. is a fluoroalkyl group, represented by As understood from the general formula (1), the fluorine-containing organosilicon compound of the present invention is a novel compound described in the literature.
フ イ ム の上記
一般式〔Ｉ〕で表わされる本発明のフッ素含有有機ケイ
素化合物は、下記一般式（ＩＩ）、式中、Ｒ及びＲｆは
前記の通り
で表わされるジクロロシランを加水分解することにより
製造される。The fluorine-containing organosilicon compound of the present invention represented by the above general formula [I] can be obtained by hydrolyzing dichlorosilane represented by the following general formula (II), where R and Rf are as described above. Manufactured by.
前記一般式［１１）において、基Ｒｆ及びＲは、それぞ
れ前記一般式（１）における基Ｒｆ及びＲに対応する基
である。In the general formula [11], the groups Rf and R correspond to the groups Rf and R in the general formula (1), respectively.
即ち、基Ｒｆは炭素原子数１〜１０のパーフルオロアル
キル基であり、好ましくは、 ＣＦ３．Ｃ４Ｆ９゜Ｃｈ
Ｆ＋ｓ 、 ＣａＦｌｓ等である。That is, the group Rf is a perfluoroalkyl group having 1 to 10 carbon atoms, preferably CF3. C4F9゜Ch
F+s, CaFls, etc.
また基Ｒは、炭素原子数１〜８の一価炭化水素基であり
、具体的にはメチル基、エチル基、プロピル基、ブチル
基等の炭素原子数８以下の低級アルキル基、シクロヘキ
シル基等のシクロアルキル基、ビニル基、アリル基、プ
ロペニル基、ブテニル基等のアルケニル基、フェニル基
、トリル基、ナフチル基等のアリール基、ベンジル基、
２−フェニルエチル基等のアラルキル基などを挙げるこ
とができる。本発明において、好適なものはアルキル基
であるが、最も好適なものはメチル基である。The group R is a monovalent hydrocarbon group having 1 to 8 carbon atoms, and specifically includes a lower alkyl group having 8 or less carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a cyclohexyl group, etc. Cycloalkyl groups, vinyl groups, allyl groups, propenyl groups, alkenyl groups such as butenyl groups, aryl groups such as phenyl groups, tolyl groups, naphthyl groups, benzyl groups,
Examples include aralkyl groups such as 2-phenylethyl group. In the present invention, an alkyl group is preferred, and a methyl group is most preferred.
上記ジクロロシランの加水分解反応は、０〜５０°Ｃ１
好ましくは０〜２０°Ｃの範囲で行なわれる。また反応
生成物である一般式［Ｉ）のフッ素含有有機ケイ素化合
物を収率よく得るためには、加水分解生成物にアルカリ
金属水酸化物を添加してクランキングを行なうことが好
適である。この際に使用されるアルカリ金属水酸化物と
しては、例えば水酸化ナトリウム、水酸化カリウム、水
酸化セシウム等を例示することができる。これらのアル
カリ金属水酸化物は、一般に、加水分解生成物１００重
量部に対して０．０１〜２重量部、特に０．１〜１重量
部の割合で使用することが望ましい。またクランキング
反応は、１５０〜３００℃、好ましくは２００〜２５０
℃の範囲で行われる。The hydrolysis reaction of the dichlorosilane is carried out at 0 to 50°C.
The temperature is preferably 0 to 20°C. Further, in order to obtain the reaction product, the fluorine-containing organosilicon compound of general formula [I], in a good yield, it is preferable to add an alkali metal hydroxide to the hydrolysis product and then perform cranking. Examples of the alkali metal hydroxide used in this case include sodium hydroxide, potassium hydroxide, and cesium hydroxide. It is generally desirable to use these alkali metal hydroxides in a proportion of 0.01 to 2 parts by weight, particularly 0.1 to 1 part by weight, based on 100 parts by weight of the hydrolysis product. Further, the cranking reaction is carried out at a temperature of 150 to 300°C, preferably 200 to 250°C.
It is carried out in the range of °C.
また前記一般式（ＩＩ）で表わされるジクロロシランは
、下記一般式（ＩＩＩ）、
ＣＨ，ＣＨ，Ｒｆ
Ｈ−５ｔ−１（ＩＩ）
式中、Ｒ及びＲｆは前記の通り、
で表わされるヒドロシランと、下記一般式［）、ＣＨｚ
ＣＨＪｆ
ＣＨ１＝ＣＨ−Ｓｉ−Ｃｊ！
（ＩＶ）
式中、Ｒ及びＲｆは前記の通り、
で表わされるビニルシランとを、白金族金属系触媒の存
在下で付加反応させることによって合成される。Further, the dichlorosilane represented by the general formula (II) can be a hydrosilane represented by the following general formula (III), CH, CH, Rf H-5t-1 (II), where R and Rf are as described above. , the following general formula [), Hz
CHJf CH1=CH-Si-Cj! (IV) In the formula, R and Rf are synthesized by carrying out an addition reaction with a vinylsilane represented by the above in the presence of a platinum group metal catalyst.
これらのヒドロシランとビニルシランとの付加反応に際
して用いられる触媒としては白金族金属系触媒を例示す
ることができ、例えば塩化白金酸、アルコール変性塩化
白金酸（米国特許第３．２２０．９７２号明細書参照）
、塩化白金酸とオレフィンとのコンプレックス（米国特
許第３．１５９．６０１号、同第３．１５９．６６２号
、同第３．７７５．４５２号明細書参照）、白金黒また
はパラジウム等をアルミナ、シリカ、カーボン等の担体
に担持させたもの、ロジウム−オレフィンコンプレック
ス等を好適に使用することができる。これらの触媒の内
、特にコンプレックスタイプのものは、アルコール系、
ケトン系、エーテル系、炭化水素系等の溶剤に溶解させ
て使用することが好適である。またこれらの白金族金属
系触媒の使用量は、一般に白金族金属換算でヒドロシラ
ン及びビニルシランの合計量に対して０．１〜５００
ｐｐｍ 、特に０．５〜２００ ｐｐ＋ｍの範囲とする
ことが望ましい。Examples of catalysts used in the addition reaction between hydrosilane and vinylsilane include platinum group metal catalysts, such as chloroplatinic acid, alcohol-modified chloroplatinic acid (see US Pat. No. 3,220,972). )
, a complex of chloroplatinic acid and olefin (see U.S. Pat. No. 3.159.601, U.S. Pat. No. 3.159.662, U.S. Pat. No. 3.775.452), platinum black or palladium, etc. with alumina, Those supported on carriers such as silica and carbon, rhodium-olefin complexes, etc. can be suitably used. Among these catalysts, especially those of complex type are alcohol-based,
It is preferable to use it by dissolving it in a ketone-based, ether-based, or hydrocarbon-based solvent. In addition, the amount of these platinum group metal catalysts used is generally 0.1 to 500% based on the total amount of hydrosilane and vinylsilane in terms of platinum group metal.
ppm, particularly preferably in the range of 0.5 to 200 pp+m.
前記ヒドロシランとビニルシランとの反応は無溶剤系で
行なうことができるが、必要により不活性溶剤、例えば
、ベンゼン、トルエン、キシレン、ｎ−ヘキサン、シク
ロヘキサン等を用いて行なうこともできる。反応温度は
、６０−１５０℃、特に８０〜１２０℃の範囲とするこ
とが好適である。The reaction between hydrosilane and vinylsilane can be carried out without a solvent, but if necessary, it can also be carried out using an inert solvent such as benzene, toluene, xylene, n-hexane, cyclohexane, etc. The reaction temperature is preferably in the range of 60-150°C, particularly 80-120°C.
フ イ ム上記の如くし
て得られる本発明のフッ素含有有機ケイ素化合物は、前
述した一般式（１）で表わされる分子構造を有する。本
発明のフッ素含有有機ケイ素化合物の代表例を以下に示
す。The fluorine-containing organosilicon compound of the present invention obtained as described above has a molecular structure represented by the general formula (1) described above. Representative examples of the fluorine-containing organosilicon compound of the present invention are shown below.
本発明のフッ素含有有機ケイ素化合物は、種々の用途に
用いることができるが、特に耐溶剤性に優れたポリシル
エチレンシロキサンの製造用原料として極めて有用であ
る。例えば本発明のフッ素含有有機ケイ素化合物を重合
することにより、側鎖にパーフロロアルキル基を有する
ポリシルエチレンシロキサンポリマーを合成することが
できる。The fluorine-containing organosilicon compound of the present invention can be used for various purposes, but is particularly useful as a raw material for producing polysilethylene siloxane having excellent solvent resistance. For example, by polymerizing the fluorine-containing organosilicon compound of the present invention, a polysilethylene siloxane polymer having a perfluoroalkyl group in the side chain can be synthesized.
このポリマーはフッ素含有率が高いため、耐溶剤性シル
エチレンシロキサンゴム、離型剤等に使用できる素材と
して特に有用である。Since this polymer has a high fluorine content, it is particularly useful as a material that can be used for solvent-resistant silethylene siloxane rubber, mold release agents, and the like.
（実施例）
実施■土
冷却管、撹拌棒、温度計及び滴下ロートを備えた５１四
つ目フラスコに、水道水１１を仕込み、滴下ロートより
、下記式、
で表わされるジクロロシラン８７１ ｇ （２，３モル
）をメタキシレンヘキサフルオライド５００ｇに溶解し
た溶液を滴下した６滴下は、フラスコを氷冷して１０℃
以下に保ちながら１時間かけて行なった。(Example) Implementation ■ A 51-meter fourth flask equipped with a soil cooling tube, a stirring rod, a thermometer, and a dropping funnel was charged with tap water 11, and from the dropping funnel, 871 g of dichlorosilane expressed by the following formula (2 , 3 moles) dissolved in 500 g of meta-xylene hexafluoride was added dropwise.The flask was cooled on ice and heated to 10°C.
This was done over an hour while keeping the temperature below.
次いで反応混合物の下層を分液し、炭酸水素ナトリウム
５６ｇを添加して中和を行なった後、濾過、減圧ストリ
ップにより加水分解生成物７９６ｇを得た。Next, the lower layer of the reaction mixture was separated and neutralized by adding 56 g of sodium hydrogen carbonate, followed by filtration and vacuum stripping to obtain 796 g of a hydrolyzed product.
この加水分解生成物に水酸化カリウム８ｇを加え、減圧
下で１６０〜２５０℃に加熱したところ、５９８ｇのク
ランキング留分を得た。これを精製することにより、沸
点８７〜８９°Ｃ／１０ｍＨｇの留分５０３ｇが得られ
た（収率６７％）。When 8 g of potassium hydroxide was added to this hydrolyzed product and heated to 160 to 250° C. under reduced pressure, 598 g of cranking fraction was obtained. By purifying this, 503 g of a fraction with a boiling point of 87 to 89°C/10 mHg was obtained (yield: 67%).
この留分について、’Ｈ−ＮＭＲ，赤外吸収スペクトル
、”Ｆ−ＮＭＲ及び元素分析を行なった結果を以下に示
す。The results of 'H-NMR, infrared absorption spectrum, F-NMR and elemental analysis of this fraction are shown below.
’Ｈ−ＮＭＲ； ＣＣ１！ ａ中、内部標準ＣＨＣｌ！
、ｓδ （ｐｐｍ）
０．２０ （ｓ、 ５ｉ−ＣＨｓ、 ６Ｈ）０．８０
（ｔ、 ５ｉ−Ｃ１ｈ、４Ｈ）０．８３ （ｓ、 ５ｔ
−ＣＨｚＣＨｚ−Ｓｉ＋ ４Ｈ）２．０７ （ｔ、 Ｃ
Ｆｓ−ＣＨ，、４Ｈ）赤外吸収スペクトル；第１図に示
す。'H-NMR; CC1! In a, internal standard CHCl!
, sδ (ppm) 0.20 (s, 5i-CHs, 6H) 0.80
(t, 5i-C1h, 4H)0.83 (s, 5t
-CHzCHz-Si+ 4H)2.07 (t, C
Fs-CH, 4H) infrared absorption spectrum; shown in FIG.
Ｃ−Ｆ ： １０００〜１４００Ｃ１−’’ ” Ｆ
Ｎ Ｍ Ｒ； ＣＦ ５ｃＯＯＨ標準ＣＦ３ ：
８．２Ｓ ｐｐ蒙
元素分析；
以上の結果から、前記留分は、
であることが確認された。C-F: 1000~1400C1-''”F
NMR; CF 5cOOH standard CF3:
8.2S pp Mongolian elemental analysis; From the above results, it was confirmed that the fraction was as follows.
実施例２
下記式、
で表わされるジクロルシラン８６８ｇをメタキシレンヘ
キサフルオライド５００ｇに溶解した溶液を用い、炭酸
水素ナトリウムの使用量を４８ｇとした以外は、実施例
１と同様の操作により加水分解生成物７６０ｇを得た。Example 2 A hydrolysis product was prepared in the same manner as in Example 1, except that a solution of 868 g of dichlorosilane represented by the following formula dissolved in 500 g of meta-xylene hexafluoride was used, and the amount of sodium bicarbonate was changed to 48 g. 760g was obtained.
この加水分解生成物に水酸化カリウム７．６ｇを加え、
減圧下で２００〜２８０°Ｃに加熱したところ、６６９
ｇのクランキング留分を得た。これを精製することによ
り、沸点１１３℃／１０ｍ＋＋Ｈｇの留分４９２ｇが得
られた（収率６６．５％）。Add 7.6 g of potassium hydroxide to this hydrolysis product,
When heated to 200-280°C under reduced pressure, 669
A cranking fraction of g was obtained. By purifying this, 492 g of a fraction with a boiling point of 113° C./10 m++Hg was obtained (yield 66.5%).
コノ留分について、’Ｈ−ＮＦ４Ｒ，赤外吸収スペクト
ル、”Ｆ−ＮＭＲ及び元素分析を行なった結果を以下に
示す。The results of 'H-NF4R, infrared absorption spectrum, F-NMR and elemental analysis of the Kono fraction are shown below.
’Ｈ−ＮＭＲ、ＣＣＩ１４中、内部標準ＣＨＣｌ ｓδ
（ｐｐ層）
０．２２ （ｓ、 ５ｔ−ＣＬ、 ６Ｈ）０．８５ （
ｓ、 ５ｉ−ＣＨ２ＣＨｚ−５ｉ＋ ４Ｈ）０．８７
（ｔ、 ５ｉ−ＣＨｚ、 ４Ｈ）２．０７ （ｔ、
Ｃｈ−ＣＨｚ、４Ｈ）赤外吸収スペクトル；第２図に示
す。'H-NMR, CCI14, internal standard CHCl sδ
(pp layer) 0.22 (s, 5t-CL, 6H) 0.85 (
s, 5i-CH2CHz-5i+ 4H) 0.87
(t, 5i-CHz, 4H)2.07 (t,
Ch-CHz, 4H) Infrared absorption spectrum; shown in Figure 2.
Ｃ−Ｆ ： １００１０００＝１４００’１９Ｆ−ＮＭ
Ｒ；ＣＦ３ＣＯＯＨ標準
ａ ： ５２．７８ ｐｐｍ
ｂ ： ５１．１７ ｐｐｌｌｌ
ｃ ： ４３．１１ ｐｐｍ
ｄ ： ８．７１ ｐｐ＋ｎ
元素分析；
ケイ素化合物の赤外吸収スペクトルを示す図である。C-F: 1001000=1400'19F-NM
R; CF3COOH standard a: 52.78 ppm b: 51.17 pplll c: 43.11 ppm d: 8.71 pp+n Elemental analysis; It is a diagram showing an infrared absorption spectrum of a silicon compound.
以上の結果から、前記留分は、From the above results, the fraction is
Claims (1)
のＲは互いに同一でも異なっていてもよく、 Ｒｆは、炭素原子数１〜１０のパーフルオロアルキル基
である、 で表わされるフッ素含有有機ケイ素化合物。(1) The following general formula [I] ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [I] In the formula, R is a monovalent hydrocarbon group with 1 to 8 carbon atoms, and the two R's are the same. The fluorine-containing organosilicon compound is represented by: Rf is a perfluoroalkyl group having 1 to 10 carbon atoms.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2171564A JPH0459784A (en) | 1990-06-29 | 1990-06-29 | Fluorine-containing organic silicon compound |
| EP91305830A EP0465129A1 (en) | 1990-06-29 | 1991-06-27 | Fluorine-containing organosilicon compound |
| US07/723,317 US5118828A (en) | 1990-06-29 | 1991-06-28 | Fluorine-containing organosilicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2171564A JPH0459784A (en) | 1990-06-29 | 1990-06-29 | Fluorine-containing organic silicon compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0459784A true JPH0459784A (en) | 1992-02-26 |
Family
ID=15925479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2171564A Pending JPH0459784A (en) | 1990-06-29 | 1990-06-29 | Fluorine-containing organic silicon compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0459784A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB999125A (en) * | 1963-03-25 | 1965-07-21 | Dow Corning | A process for preparing organosilicon polymers |
-
1990
- 1990-06-29 JP JP2171564A patent/JPH0459784A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB999125A (en) * | 1963-03-25 | 1965-07-21 | Dow Corning | A process for preparing organosilicon polymers |
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