JP2781494B2 - Fluorine-containing organosilicon compounds - Google Patents
Fluorine-containing organosilicon compoundsInfo
- Publication number
- JP2781494B2 JP2781494B2 JP4146666A JP14666692A JP2781494B2 JP 2781494 B2 JP2781494 B2 JP 2781494B2 JP 4146666 A JP4146666 A JP 4146666A JP 14666692 A JP14666692 A JP 14666692A JP 2781494 B2 JP2781494 B2 JP 2781494B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- fluorine
- embedded image
- integer
- containing organosilicon
- 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.)
- Expired - Fee Related
Links
- 229910052731 fluorine Inorganic materials 0.000 title claims description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title description 10
- 239000011737 fluorine Substances 0.000 title description 10
- 150000003961 organosilicon compounds Chemical class 0.000 title description 9
- 239000010702 perfluoropolyether Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 9
- -1 lithium aluminum hydride Chemical compound 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000003377 silicon compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- YZBBUYKPTHDZHF-KNVGNIICSA-N (3R)-7,2'-dihydroxy-4'-methoxyisoflavanol Chemical compound OC1=CC(OC)=CC=C1[C@H]1C(O)C2=CC=C(O)C=C2OC1 YZBBUYKPTHDZHF-KNVGNIICSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Polyethers (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は文献未載の新規な含フッ
素有機けい素化合物、特には耐溶剤性、耐薬品性であ
り、コーティング材料用素材、離型剤用素材などの原料
および架橋剤として有用とされる含フッ素有機けい素化
合物に関するものである。BACKGROUND OF THE INVENTION The present invention relates to a novel fluorine-containing organosilicon compound which has not been described in any literature, particularly to a solvent-resistant and chemical-resistant material, such as a material for a coating material and a material for a release agent, and crosslinking. The present invention relates to a fluorine-containing organic silicon compound useful as an agent.
【０００２】[0002]
【発明の構成】本発明の含フッ素有機けい素化合物は一
般式（１）The fluorine-containing organosilicon compound of the present invention has the general formula (1)
【化３】 で示され、このＲｆは一般式Embedded image Where Rf is a general formula
【化４】 で示されるもので、ａは１〜16の整数、ｂは０〜８の整
数、ｃは０または１の整数であるがｂ＝ｃ＝０は除かれ
る１価のパーフルオロポリエーテル基、Ｒを例示すると
アルキル基の例としてはメチル基、エチル基、プロピル
基、ブチル基、アルケニル基の例としてはビニル基、ア
リル基、アリール基の例としてはフェニル基、トリル
基、これら例示の基の炭素原子に結合している水素原子
の一部または全部をハロゲン原子、シアノ基で置換した
例えばクロロメチル基、トリフルオロプロピル基、シア
ノエチル基などの非置換または置換の１価炭化水素基で
あり、ＸはＦまたはＣＦ3 であるものである。Embedded image Wherein a is an integer of 1 to 16, b is an integer of 0 to 8, c is an integer of 0 or 1, but b = c = 0 is excluded, but a monovalent perfluoropolyether group ; To illustrate
Methyl group Examples of the alkyl group, an ethyl group, a propyl group, butyl group, vinyl group and examples of the alkenyl group, an allyl group, a phenyl group Examples of the aryl group, a tolyl group, a carbon atom of these illustrative groups Some or all of the bonded hydrogen atoms have been replaced with halogen atoms or cyano groups
Such as chloromethyl group, trifluoropropyl group, an unsubstituted or substituted monovalent hydrocarbon group such as cyanoethyl group
There, X is one F or CF 3.
【０００３】この含フッ素有機けい素化合物としては下
記のものが例示されるがこれらは代表例であり、本発明
の含フッ素有機けい素化合物はこれに限定されるもので
はない。The following are examples of the fluorine-containing organic silicon compound, but these are typical examples, and the fluorine-containing organic silicon compound of the present invention is not limited thereto.
【化５】 Embedded image
【化６】 Embedded image
【化７】 Embedded image
【化８】 Embedded image
【０００４】本発明の分子鎖末端にヒドロシリル基を有
する含フッ素有機けい素化合物の製造は、例えば式The production of the fluorine-containing organosilicon compound having a hydrosilyl group at the terminal of the molecular chain of the present invention can be carried out, for example, by the following method:
【化９】 （ここにＲｆは前記に同じ、ＹはＦ、Ｃｌ、Ｂｒ、Ｉな
どのハロゲン原子）で示されるシリルパーフルオロポリ
エーテルに還元剤を反応させることによって合成するこ
とができ、これは還元剤を非水溶媒に懸濁溶解させ、こ
こに上記したシリルパーフルオロポリエーテルを滴下反
応させればよい。Embedded image (Where Rf is the same as above, and Y is a halogen atom such as F, Cl, Br, I, etc.), which can be synthesized by reacting a silyl perfluoropolyether with a reducing agent. What is necessary is just to suspend and dissolve in a non-aqueous solvent, and to react the above-mentioned silyl perfluoropolyether dropwise.
【０００５】ここに使用する還元剤としては水素化リチ
ウムアルミニウム、水素化ほう素ナトリウムなどが例示
されるが、この使用量は目的とする含フッ素有機けい素
化合物のヒドロシリル末端基に対して４分の１から３倍
モル、好ましくは２分の１から等モル程度の範囲とすれ
ばよい。また、この溶媒としてはＴＨＦ、ジエチルエー
テル、ＤＭＩ、ＤＭＦ、ＤＭＳＯなどの脱水した非水溶
媒とすればよい。なお、この反応は大部分が室温でも速
やかに進行するが、反応の遅いときには40〜100 ℃の範
囲の適当な温度に加熱すればよい。Examples of the reducing agent used herein include lithium aluminum hydride and sodium borohydride. The amount of the reducing agent used is 4 minutes based on the hydrosilyl terminal group of the target fluorine-containing organosilicon compound. The molar ratio may be about 1 to 3 times, preferably about 1/2 to equimolar. The solvent may be a dehydrated non-aqueous solvent such as THF, diethyl ether, DMI, DMF, DMSO and the like. Most of the reaction proceeds rapidly even at room temperature, but when the reaction is slow, the reaction may be heated to an appropriate temperature in the range of 40 to 100 ° C.
【０００６】このようにして製造された本発明の末端に
ヒドロシリル基を有する含フッ素有機けい素化合物を例
えば式 Ｒｆ−ＣＨ＝ＣＨ2 （Ｒｆは前記に同じ） で示される不飽和基を含有するパーフルオロポリエーテ
ルと付加反応触媒の存在下に付加反応させることによっ
てパーフルオロポリエーテル基含有シランを合成するこ
とができるが、このポリマーはフッ素含有率の高いシラ
ンであることから、耐溶剤性、耐薬品性に優れており、
このものはコーティング材料用素材として、また低表面
エネルギーを有するシランであることから離型剤などに
使用できる素材として有用とされる。The fluorinated organosilicon compound having a hydrosilyl group at the terminal thus produced according to the present invention contains, for example, an unsaturated group represented by the formula Rf-CH = CH 2 (Rf is as defined above). By performing an addition reaction in the presence of a perfluoropolyether and an addition reaction catalyst, a perfluoropolyether group-containing silane can be synthesized, but since this polymer is a silane having a high fluorine content, solvent resistance, Excellent chemical resistance,
This is useful as a material for coating materials and as a material that can be used as a release agent because it is a silane having low surface energy.
【０００７】[0007]
【実施例】つぎに本発明の実施例をあげる。 実施例１ 撹拌機、温度計、ジムロート、滴下ロートを取りつけた
100mlの三ッ口フラスコに、窒素ガスを50ml／分の流量
で流しながら水素化リチウムアルミニウム0.38g とＴＨ
Ｆ 10gを仕込み、撹拌しながらここに式Next, examples of the present invention will be described. Example 1 A stirrer, a thermometer, a Dim funnel, and a dropping funnel were attached.
While flowing nitrogen gas into a 100 ml three-necked flask at a flow rate of 50 ml / min, 0.38 g of lithium aluminum hydride and TH
Add 10g of F and stir here
【化１０】 で示されるクロロシリルパーフルオロポリエーテル 10.
7gを滴下し、滴下終了後室温で30分間熟成したのち、未
反応の水素化リチウムアルミニウムをろ別し、減圧蒸留
したところ、沸点98℃／70mmHgの留分8.3gが得られた。Embedded image Chlorosilyl perfluoropolyether represented by 10.
After dropping 7 g, the mixture was aged at room temperature for 30 minutes after completion of the dropping, and unreacted lithium aluminum hydride was filtered off and distilled under reduced pressure to obtain 8.3 g of a fraction having a boiling point of 98 ° C./70 mmHg.
【０００８】ついで、この留分をＩＲ、 1Ｈ−ＮＭＲ、
19Ｆ−ＮＭＲおよびＧＣ−ＭＡＳＳおよび元素分析によ
り分析したところ、下記のとおりの結果が得られたこと
から、このものは式Then, this fraction is subjected to IR, 1 H-NMR,
When analyzed by 19 F-NMR, GC-MASS and elemental analysis, the following results were obtained.
【化１１】 で示されるものであることが確認された。Embedded image Was confirmed.
【０００９】（分析結果） ＧＣ−ＭＡＳＳ： ＭＷ＝538 ＩＲ（図−１参照） νSi-H：2,130cm-1 νC-F ：1,100 〜1,300cm-1 1 Ｈ−ＮＭＲ（ＴＭＳ標準、ｐｐｍ） 0.27（ｄ，Ｓｉ−ＣＨ3 ，６Ｈ） 0.91（ｍ，Ｓｉ−ＣＨ2 ，２Ｈ） 2.23（ｍ，ＣＦ−ＣＨ2 ，２Ｈ） 3.98（ｍ，Ｓｉ−Ｈ ，１Ｈ）19 Ｆ−ＮＭＲ（ＣＦ3 ＣＯＯＨ標準、ｐｐｍ）[0009] (Analysis results) GC-MASS: MW = 538 IR ( see Fig. -1) ν Si-H: 2,130cm -1 ν CF: 1,100 ~1,300cm -1 1 H-NMR (TMS standard, ppm) 0.27 (d, Si-CH 3, 6H) 0.91 (m, Si-CH 2, 2H) 2.23 (m, CF-CH 2, 2H) 3.98 (m, Si-H, 1H) 19 F-NMR (CF 3 COOH Standard, ppm)
【化１２】 元素分析 Ｃ％ Ｈ％ Ｓｉ％ Ｆ％ Ｏ％ 計算値 26.8 2.0 5.2 60.0 6.0 実測値 26.5 1.8 5.0 60.2 5.8Embedded image Elemental analysis C% H% Si% F% O% Calculated value 26.8 2.0 5.2 60.0 6.0 Actual value 26.5 1.8 5.0 60.2 5.8
【００１０】実施例２ 撹拌機、温度計、ジムロード、滴下ロートを取りつけた
100mlの三ッ口フラスコに、窒素ガスを50ml／分の流量
で流しながら水素化リチウムアルミニウム 0.38gとＴＨ
Ｆ10g を仕込み、撹拌しながらここに式Example 2 A stirrer, a thermometer, a Jim Lord, and a dropping funnel were attached.
While flowing nitrogen gas at a flow rate of 50 ml / min into a 100 ml three-necked flask, 0.38 g of lithium aluminum hydride and TH
Add 10g of F
【化１３】 で示されるクロロシリルパーフルオロポリエーテル9.1g
を滴下し、滴下終了後室温で30分間熟成したのち、未反
応の水素化リチウムアルミニウムをろ別し、減圧蒸留し
たところ、沸点 100℃／70mmHgの留分6.9gが得られた。Embedded image In chlorosilyl perfluoro port Rieteru 9.1g shown
After ripening, the mixture was aged at room temperature for 30 minutes, unreacted lithium aluminum hydride was filtered off, and distilled under reduced pressure to obtain 6.9 g of a fraction having a boiling point of 100 ° C./70 mmHg.
【００１１】ついで、この留分をＩＲ、 1Ｈ−ＮＭＲ、
19Ｆ−ＮＭＲおよびＧＣ−ＭＡＳＳおよび元素分析によ
り分析したところ、下記のとおりの結果が得られたこと
から、このものは式Then, this fraction was subjected to IR, 1 H-NMR,
When analyzed by 19 F-NMR, GC-MASS and elemental analysis, the following results were obtained.
【化１４】 で示されるものであることが確認された。Embedded image Was confirmed.
【００１２】（分析結果） ＧＣ−ＭＡＳＳ： ＭＷ＝538 ＩＲ（図−２参照） νSi-H：2,120cm-1 νC-F ：1,100 〜1,300cm-1 1 Ｈ−ＮＭＲ（ＴＭＳ標準、ｐｐｍ） 0.24（ｄ，Ｓｉ−ＣＨ3 ，６Ｈ） 0.87（ｍ，Ｓｉ−ＣＨ2 ，２Ｈ） 2.09（ｍ，ＣＦ−ＣＨ2 ，２Ｈ） 3.99（ｍ，Ｓｉ−Ｈ ，１Ｈ）19 Ｆ−ＮＭＲ（ＣＦ3 ＣＯＯＨ標準、ｐｐｍ）[0012] (Analysis results) GC-MASS: MW = 538 IR ( see Fig. -2) ν Si-H: 2,120cm -1 ν CF: 1,100 ~1,300cm -1 1 H-NMR (TMS standard, ppm) 0.24 (d, Si-CH 3, 6H) 0.87 (m, Si-CH 2, 2H) 2.09 (m, CF-CH 2, 2H) 3.99 (m, Si-H, 1H) 19 F-NMR (CF 3 COOH Standard, ppm)
【化１５】 元素分析 Ｃ％ Ｈ％ Ｓｉ％ Ｆ％ Ｏ％ 計算値 26.8 2.0 5.2 60.0 6.0 実測値 27.0 1.9 5.0 60.3 5.8Embedded image Elemental analysis C% H% Si% F% O% Calculated 26.8 2.0 5.2 60.0 6.0 Actual 27.0 1.9 5.0 60.3 5.8
【００１３】[0013]
【発明の効果】本発明は文献未載の新規な含フッ素有機
けい素化合物であり、これは前記したような一般式
（１）で示されるものであるが、このものは耐溶剤性、
耐薬品性に優れており、コーティング機材用素材、離型
剤用素材などの原料および架橋剤として有用されるもの
である。The present invention is a novel fluorine-containing organosilicon compound which has not been described in any literature and is represented by the above-mentioned general formula (1).
It has excellent chemical resistance and is useful as a raw material and a cross-linking agent for materials for coating equipment and materials for release agents.
【図面の簡単な説明】[Brief description of the drawings]
【図１】本説明の実施例１で得られた含フッ素有機けい
素化合物の赤外吸収スペクトル図（ＩＲ）を示したもの
である。FIG. 1 shows an infrared absorption spectrum (IR) of a fluorinated organosilicon compound obtained in Example 1 of the present description.
【図２】本説明の実施例２で得られた含フッ素有機けい
素化合物の赤外吸収スペクトル図（ＩＲ）を示したもの
である。FIG. 2 is an infrared absorption spectrum (IR) of the fluorinated organosilicon compound obtained in Example 2 of the present description.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 松田 高至 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 (58)調査した分野(Int.Cl.6，ＤＢ名) ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuing from the front page (72) Inventor Koji Matsuda 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Pref. Shin-Etsu Chemical Co., Ltd. Silicone Electronic Materials Research Laboratory (58) Field surveyed (Int. 6 , DB name) CA (STN) REGISTRY (STN)
Claims (1)
または１の整数であるがｂ＝ｃ＝０は除く）で示される
１価パーフルオロポリエーテル基、Ｒは炭素数１〜７
の、アルキル基、アルケニル基、アリール基またはこれ
らの基の炭素原子に結合している水素原子の一部または
全部をハロゲン原子、シアノ基で置換した基から選択さ
れる非置換または置換の１価炭化水素基、ＸはＦまたは
ＣＦ3 〕で示される含フッ素有機けい素化合物。1. A compound of the general formula [Where Rf is a general formula: (Where a is an integer of 1 to 16, b is an integer of 0 to 8, c is 0
Or a monovalent perfluoropolyether group represented by the formula : R is an integer of 1 except b = c = 0),
An alkyl group, an alkenyl group, an aryl group or
Some of the hydrogen atoms bonded to the carbon atoms of these groups or
All selected from halogen atoms and groups substituted with cyano groups.
An unsubstituted or substituted monovalent hydrocarbon group, and X is F or CF 3 ].
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4146666A JP2781494B2 (en) | 1992-05-12 | 1992-05-12 | Fluorine-containing organosilicon compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4146666A JP2781494B2 (en) | 1992-05-12 | 1992-05-12 | Fluorine-containing organosilicon compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05310912A JPH05310912A (en) | 1993-11-22 |
| JP2781494B2 true JP2781494B2 (en) | 1998-07-30 |
Family
ID=15412878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4146666A Expired - Fee Related JP2781494B2 (en) | 1992-05-12 | 1992-05-12 | Fluorine-containing organosilicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2781494B2 (en) |
-
1992
- 1992-05-12 JP JP4146666A patent/JP2781494B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05310912A (en) | 1993-11-22 |
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