JPH07247293A - Medium of fluorine-containing silicon compound - Google Patents
Medium of fluorine-containing silicon compoundInfo
- Publication number
- JPH07247293A JPH07247293A JP6040923A JP4092394A JPH07247293A JP H07247293 A JPH07247293 A JP H07247293A JP 6040923 A JP6040923 A JP 6040923A JP 4092394 A JP4092394 A JP 4092394A JP H07247293 A JPH07247293 A JP H07247293A
- Authority
- JP
- Japan
- Prior art keywords
- medium
- fluorine
- containing silicon
- silicon compound
- group
- 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
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、フルオロアルコキシ基
を有する含フッ素ケイ素化合物からなる媒体に関する。
さらに詳しくは、該含フッ素ケイ素化合物からなる潤滑
剤、発泡剤、樹脂改質剤、離型剤、熱媒、絶縁媒体、不
活性媒体、レベリング剤に関する。TECHNICAL FIELD The present invention relates to a medium composed of a fluorine-containing silicon compound having a fluoroalkoxy group.
More specifically, the present invention relates to a lubricant, a foaming agent, a resin modifier, a release agent, a heat medium, an insulating medium, an inert medium, and a leveling agent, which are made of the fluorine-containing silicon compound.
【０００２】[0002]
【従来の技術】従来、潤滑剤、樹脂の発泡剤、樹脂改質
剤、離型剤、熱媒、絶縁媒体、電子部品のグロスリーク
テスト、サーマルショックテスト、リキッドバーンイン
テスト等のテスト液等に用いられる不活性媒体、イン
ク、塗料、ワックス等へ添加して用いられるレベリング
剤等として広く用いられる鉱物油系媒体やシリコーン油
は可燃性であるため、防災面からより難燃性、あるいは
不燃性の媒体が望まれる。その目的に適した媒体とし
て、トリクロロフルオロメタン（ＣＦＣ１１）や１，
１，２−トリクロロ−１，２，２−トリフルオロエタン
（ＣＦＣ１１３）等に代表される塩素化フッ素化炭化水
素や、鎖状または環状のパーフルオロアルカンやパーフ
ロオロアミンやパーフルオロエーテル等のパーフルオロ
化合物は、浸透性に優れ、不燃性、低毒性で、ゴムやプ
ラスチックへの影響が小さく、熱・化学的にも安定であ
るため優れた媒体として広く用いられている。2. Description of the Related Art Conventionally, it has been used as a lubricant, a resin foaming agent, a resin modifier, a release agent, a heat medium, an insulating medium, a test liquid such as a gross leak test, a thermal shock test, a liquid burn-in test for electronic parts. Mineral oil media and silicone oils, which are widely used as leveling agents used by adding to inert media, inks, paints, waxes, etc., are flammable, so they are more flame-retardant or non-flammable in terms of disaster prevention. The medium of is desired. As a medium suitable for that purpose, trichlorofluoromethane (CFC11) or 1,
Chlorinated fluorinated hydrocarbons typified by 1,2-trichloro-1,2,2-trifluoroethane (CFC113) and the like, and chain or cyclic perfluoroalkanes, perfluoroamines and perfluoroethers and other perfluoroethers. Fluoro compounds are widely used as excellent media because they have excellent penetrability, nonflammability and low toxicity, have little effect on rubber and plastics, and are stable thermally and chemically.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、このよ
うに優れた特徴を有する塩素化フッ素化炭化水素は、こ
の構成元素の１つである塩素原子が触媒となり、地球を
取り巻くオゾン層を破壊することが明らかになったこと
から、ＣＦＣ１１やＣＦＣ１１３は１９９６年に全廃さ
れることが国際的に取り決められた。一方パーフルオロ
化合物は、その優れた安定性が故に、大気中に放出され
た場合の寿命が極めて長く、従って地球温暖化効果が極
めて大きくその使用は好ましいものではない。このよう
な問題に対処するためにはこれらに代わる新しい媒体の
開発が不可欠であるが、未だ有効な代替物が見いだされ
ていない状況にある。本発明は、以上の状況に鑑みてな
されたものであり、オゾン層の破壊を引き起こすことな
く、地球温暖化効果も小さい、優れた媒体を提供するも
のである。However, in the chlorinated fluorinated hydrocarbon having such excellent characteristics, the chlorine atom, which is one of the constituent elements, serves as a catalyst to destroy the ozone layer surrounding the earth. It became clear that CFC11 and CFC113 were abolished in 1996, and it was agreed internationally. On the other hand, the perfluoro compound has a very long life when it is released into the atmosphere due to its excellent stability, and therefore, the global warming effect is extremely large and its use is not preferable. In order to deal with such problems, the development of new media to replace them is indispensable, but there is still no effective alternative found. The present invention has been made in view of the above circumstances, and provides an excellent medium that does not cause destruction of the ozone layer and has a small global warming effect.
【０００４】[0004]
【課題を解決するための手段】本発明は、上記従来技術
の現状に鑑みて鋭意研究を重ねた結果、特定の構造を有
する含フッ素ケイ素化合物、即ちフルオロアルコキシ基
を有する下記一般式（１）の含フッ素ケイ素化合物から
なる媒体が、分子中に塩素を含有しないのでオゾン層を
破壊する恐れが全くなく、また分子中に水素原子を含有
するので大気中寿命が短い、即ち地球温暖化効果が小さ
く、従来使用されていたＣＦＣ１１３等と同様の優れた
浸透性や安定性を有し、低温流動性にも優れ、金属、プ
ラスチック、エラストマーを侵すことのない優れた媒体
であることを見いだし、本発明を完成するに至った。即
ち、本発明は下記一般式（１）で表され、且つ分子内に
少なくとも１個以上の水素原子を有する、フルオロアル
コキシ基を有する含フッ素ケイ素化合物からなる媒体を
提供するものである。Means for Solving the Problems The present invention has been earnestly studied in view of the state of the art described above, and as a result, a fluorine-containing silicon compound having a specific structure, that is, the following general formula (1) having a fluoroalkoxy group Since the medium composed of the fluorine-containing silicon compound does not contain chlorine in the molecule, there is no fear of destroying the ozone layer, and since it contains hydrogen atoms in the molecule, it has a short atmospheric life, that is, it has a global warming effect. It was found to be a small medium that has excellent permeability and stability similar to CFC113, etc. that have been used conventionally, has excellent low-temperature fluidity, and does not attack metals, plastics, and elastomers. The invention was completed. That is, the present invention provides a medium represented by the following general formula (1), which comprises a fluorine-containing silicon compound having a fluoroalkoxy group and having at least one hydrogen atom in the molecule.
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】本発明における媒体とは物質そのものの移
動や物質間の熱移動等を媒介する化合物であって、具体
的には潤滑剤、発泡剤、樹脂改質剤、離型剤、熱媒、絶
縁媒体、不活性媒体、レベリング剤等として用いられる
機能性流体をいう。本発明において提示される一般式
（１）中で、Ｒ1で表される炭素原子数１〜１２の直鎖
または分岐を有するフルオロアルキル基としては、例え
ば、２，２−ジフルオロエチル基、２，２，２−トリフ
ルオロエチル基、３，３−ジフルオロプロピル基、３，
３，３−トリフルオロロピル基、２，２，３，３−テト
ラフルオロプロピル基、２，２，３，３，３−ペンタフ
ルオロプロピル基、１，１，１，３，３，３−ヘキサフ
ルオロイソプロピル基、１，１，３，３−テトラフルオ
ロイソプロピル基、２−トリフルオロメチル−３，３，
３−トリフルオロプロピル基、２，２，３，４，４，４
−ヘキサフルオロブチル基、ノナフルオロ−ｔ−ブチル
基、２，２，３，３，４，４，４−ヘプタフルオロブチ
ル基、２，２，３，３，４，４，５，５，５−ノナフル
オロペンチル基、２，２，３，３，４，４，５，５，
６，６，６−ウンデカフルオロヘキシル基等が挙げら
れ、例えば２−パーフルオロプロポキシ−２，３，３，
３−テトラフルオロプロポキシ基のように鎖中に酸素原
子を含んでいてもよい。これらの基のうち、フッ素原子
が２個以上で、酸素原子と隣接した炭素原子上にフッ素
原子を持たない、炭素原子数２〜９の直鎖または分岐を
有するフルオロアルキル基が好ましく、中でもフッ素原
子が５個以上のフルオロアルキル基を有する化合物は加
水分解しにくいのでさらに好ましい。The medium in the present invention is a compound that mediates the movement of substances themselves, the heat transfer between substances, etc. Specifically, the lubricant, the foaming agent, the resin modifier, the release agent, the heat medium, A functional fluid used as an insulating medium, an inert medium, a leveling agent, or the like. In the general formula (1) presented in the present invention, as the linear or branched fluoroalkyl group having 1 to 12 carbon atoms represented by R 1 , for example, 2,2-difluoroethyl group, 2 , 2,2-trifluoroethyl group, 3,3-difluoropropyl group, 3,
3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,1,3,3,3-hexa Fluoroisopropyl group, 1,1,3,3-tetrafluoroisopropyl group, 2-trifluoromethyl-3,3,3
3-trifluoropropyl group, 2,2,3,4,4,4
-Hexafluorobutyl group, nonafluoro-t-butyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 2,2,3,3,4,4,5,5,5- Nonafluoropentyl group, 2,2,3,3,4,4,5,5,
6,6,6-undecafluorohexyl group and the like, for example, 2-perfluoropropoxy-2,3,3,3.
An oxygen atom may be contained in the chain like a 3-tetrafluoropropoxy group. Of these groups, a fluoroalkyl group having two or more fluorine atoms, having no fluorine atom on the carbon atom adjacent to the oxygen atom, and having a linear or branched chain having 2 to 9 carbon atoms is preferable, and fluorine is particularly preferable. A compound having a fluoroalkyl group having 5 or more atoms is more preferable because it is difficult to hydrolyze.
【０００７】また本発明においてＲ2のアルキル基とし
ては、同一または相異なるアルキル基で、具体的にはメ
チル基、エチル基、プロピル基、イソプロピル基、ブチ
ル基、イソブチル基、２−ブチル基、ｔ−ブチル基、ペ
ンチル基、ヘキシル基、ヘプチル基、オクチル基等が挙
げられる。In the present invention, the alkyl group of R 2 is the same or different alkyl group, specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, 2-butyl group, Examples thereof include t-butyl group, pentyl group, hexyl group, heptyl group and octyl group.
【０００８】本発明の上記一般式（１）で表される、フ
ルオロアルコキシ基を有する含フッ素ケイ素化合物とし
ては、具体的には、２，２，２−トリフルオロエトキシ
トリメチルシラン、２，２，３，３，３−ペンタフルオ
ロプロポキシトリメチルシラン、２，２，３，３，４，
４，４−ヘプタフルオロブトキシトリメチルシラン、
２，２，３，３，４，４，５，５，５−ノナフルオロペ
ンチルオキシトリメチルシラン、２，２，３，３，３−
ペンタフルオロプロポキシトリエチルシラン、２，２，
３，３，３−ペンタフルオロプロポキシジメチルエチル
シラン、１−Ｈ−ヘキサフルオロイソプロポキシトリメ
チルシラン、ノナフルオロ−ｔ−ブトキシトリメチルシ
ラン、１，１−ビス（トリフルオロメチル）エトキシト
リメチルシラン、２，２，３，３−テトラフルオロプロ
ポキシトリメチルシラン、２，２，３，４，４，４−ヘ
キサフルオロブトキシトリメチルシラン、ジメチルビス
（２，２，２−トリフルオロエトキシ）シラン、メチル
トリス（２，２，２−トリフルオロエトキシ）シラン、
エチルトリス（２，２，２−トリフルオロエトキシ）シ
ラン、プロピルトリス（２，２，２−トリフルオロエト
キシ）シラン、ジエチルビス（２，２，２−トリフルオ
ロエトキシ）シラン、ジメチルビス（１，１，１，３，
３，３−ヘキサフルオロイソプロポキシ）シラン、ジエ
チルビス（１，１，１，３，３，３−ヘキサフルオロイ
ソプロポキシ）シラン、メチルトリス（２，２，３，３
−テトラフルオロプロポキシ）シラン、ジメチルビス
（１，１，３，３−テトラフルオロイソプロポキシ）シ
ラン、ジメチルビス（２，２，３，４，４，４−ヘキサ
フルオロブトキシ）シラン、ジメチルビス（２，２，
３，３，４，４，４−ヘプタフルオロブトキシ）シラ
ン、ジメチルビス（２，２，３，３，３−ペンタフルオ
ロプロポキシ）シラン、メチルトリス（２，２，３，
３，３−ペンタフルオロプロポキシ）シラン、ジエチル
ビス（２，２，３，３，３−ペンタフルオロプロポキ
シ）シラン、エチルトリス（２，２，３，３，３−ペン
タフルオロプロポキシ）シラン、エチルメチルビス
（２，２，３，３，３−ペンタフルオロプロポキシ）シ
ラン、プロピルトリス（２，２，３，３，３−ペンタフ
ルオロプロポキシ）シラン、ブチルトリス（２，２，
３，３，３−ペンタフルオロプロポキシ）シラン、テト
ラキス（２，２，２−トリフルオロエトキシ）シラン、
テトラキス（２，２，３，３，３−ペンタフルオロプロ
ポキシ）シラン、テトラキス（１，１，１，３，３，３
−ヘキサフルオロイソプロポキシ）シラン、メチルトリ
ス（１，１，１，３，３，３−ヘキサフルオロイソプロ
ポキシ）シラン、ジメチルビス（ノナフルオロ−ｔ−ブ
トキシ）シラン、メチルトリス（ノナフルオロ−ｔ−ブ
トキシ）シラン等が挙げられる。Specific examples of the fluorine-containing silicon compound having a fluoroalkoxy group represented by the above general formula (1) of the present invention include 2,2,2-trifluoroethoxytrimethylsilane, 2,2,2. 3,3,3-pentafluoropropoxytrimethylsilane, 2,2,3,3,4
4,4-heptafluorobutoxytrimethylsilane,
2,2,3,3,4,4,5,5,5-nonafluoropentyloxytrimethylsilane, 2,2,3,3,3-
Pentafluoropropoxytriethylsilane, 2,2
3,3,3-Pentafluoropropoxydimethylethylsilane, 1-H-hexafluoroisopropoxytrimethylsilane, nonafluoro-t-butoxytrimethylsilane, 1,1-bis (trifluoromethyl) ethoxytrimethylsilane, 2,2,2 3,3-tetrafluoropropoxytrimethylsilane, 2,2,3,4,4,4-hexafluorobutoxytrimethylsilane, dimethylbis (2,2,2-trifluoroethoxy) silane, methyltris (2,2,2 -Trifluoroethoxy) silane,
Ethyltris (2,2,2-trifluoroethoxy) silane, propyltris (2,2,2-trifluoroethoxy) silane, diethylbis (2,2,2-trifluoroethoxy) silane, dimethylbis (1,1,1) 1, 3,
3,3-hexafluoroisopropoxy) silane, diethylbis (1,1,1,3,3,3-hexafluoroisopropoxy) silane, methyltris (2,2,3,3)
-Tetrafluoropropoxy) silane, dimethylbis (1,1,3,3-tetrafluoroisopropoxy) silane, dimethylbis (2,2,3,4,4,4-hexafluorobutoxy) silane, dimethylbis (2 , 2,
3,3,4,4,4-heptafluorobutoxy) silane, dimethylbis (2,2,3,3,3-pentafluoropropoxy) silane, methyltris (2,2,3,3)
3,3-pentafluoropropoxy) silane, diethylbis (2,2,3,3,3-pentafluoropropoxy) silane, ethyltris (2,2,3,3,3-pentafluoropropoxy) silane, ethylmethylbis ( 2,2,3,3,3-pentafluoropropoxy) silane, propyltris (2,2,3,3,3-pentafluoropropoxy) silane, butyltris (2,2,2
3,3,3-pentafluoropropoxy) silane, tetrakis (2,2,2-trifluoroethoxy) silane,
Tetrakis (2,2,3,3,3-pentafluoropropoxy) silane, Tetrakis (1,1,1,3,3,3)
-Hexafluoroisopropoxy) silane, methyltris (1,1,1,3,3,3-hexafluoroisopropoxy) silane, dimethylbis (nonafluoro-t-butoxy) silane, methyltris (nonafluoro-t-butoxy) silane, etc. Is mentioned.
【０００９】これらの中で、フルオロアルコキシ基の数
が２〜３個である化合物が、不燃または難燃性で、且つ
加水分解しにくいのでより好ましい。これらのフルオロ
アルコキシ基を有する含フッ素ケイ素化合物は、公知の
方法により製造することができる。一般的には、含フッ
素アルコール（例えば、ＲＯＨ：Ｒは前記Ｒ1と同じ）
を相当するクロロシランと反応させることで極めて容易
に得られる（例えば、Ｊ．Ｐｏｌａら、Ｃｏｌｌｅｃ
ｔ．Ｃｚｅｃｈ．Ｃｈｅｍ．Ｃｏｍｍｕｎ．、４４巻、
７５０〜７５５ページ、１９７９年）。Among these, compounds having 2 to 3 fluoroalkoxy groups are more preferable because they are nonflammable or flame retardant and hardly hydrolyzed. The fluorine-containing silicon compound having these fluoroalkoxy groups can be produced by a known method. Generally, a fluorine-containing alcohol (for example, ROH: R is the same as R 1 )
Can be obtained very easily by reacting with the corresponding chlorosilane (see, for example, J. Pola et al., Collec).
t. Czech. Chem. Commun. , 44 volumes,
750-755, 1979).
【００１０】該含フッ素ケイ素化合物からなる媒体は、
沸点範囲が適当な範囲にあり、表面張力が小さいために
浸透性に優れ、熱及び化学的にも安定で、プラスチック
等の素材に悪影響を与えず、低毒性で、フッ素を多く含
むため難燃または不燃の媒体である。従って、潤滑剤と
して用いた場合、その表面エネルギーが小さいため、良
好な潤滑性を発揮する上、低温での流動性にも優れてい
る。また、樹脂の発泡剤として、例えば押し出し発泡に
用いた場合には、高温で樹脂との適度な相溶性を有する
ため好適に用いることができる。樹脂改質剤として樹脂
に混合した場合は、樹脂に耐薬品性、潤滑性、離型性、
非粘着性、撥水・撥油性を付与することができる。離型
剤としてはゴムの成型や樹脂の成型時の付着防止剤とし
て用いた場合には良好な剥離性が得られる。熱媒として
用いた場合は、低融点、低粘度なため、低温槽や恒温槽
の媒体として好適に用いることができる。絶縁媒体とし
て用いた場合には、高い絶縁性能を示し、低温での流動
性にも優れている。不活性媒体としては、低温での流動
性にも優れた安定な媒体として、グロスリークテスト、
サーマルショックテスト、リキッドバーンインテスト等
のテスト液や電子部品用保存液として用いることができ
る。またレベリング剤としてインク、塗料、ワックスへ
添加した場合には、濡れ性が著しく改善される。The medium comprising the fluorine-containing silicon compound is
It has an appropriate boiling point range, excellent surface permeability due to its low surface tension, is stable to heat and chemicals, does not adversely affect plastics and other materials, has low toxicity, and contains a large amount of fluorine, making it flame-retardant. Or a non-combustible medium. Therefore, when used as a lubricant, its surface energy is small, so that it exhibits good lubricity and is also excellent in fluidity at low temperatures. Further, when used as a foaming agent for resin, for example, in extrusion foaming, it has suitable compatibility with the resin at a high temperature, and therefore can be suitably used. When mixed with a resin as a resin modifier, the resin has chemical resistance, lubricity, releasability,
Non-adhesiveness and water / oil repellency can be imparted. When used as an anti-adhesion agent at the time of molding rubber or resin as a release agent, good releasability is obtained. When used as a heat medium, it has a low melting point and a low viscosity, and thus can be suitably used as a medium for a low temperature bath or a constant temperature bath. When used as an insulating medium, it exhibits high insulation performance and is excellent in fluidity at low temperatures. As an inert medium, a gross leak test, as a stable medium excellent in fluidity at low temperature,
It can be used as a test solution for a thermal shock test, a liquid burn-in test, etc., or as a storage solution for electronic parts. Further, when added as a leveling agent to ink, paint or wax, the wettability is remarkably improved.
【００１１】これらの媒体は単独あるいはそれぞれ混合
して使用することができる。また、従来使用されている
鉱油系媒体やシリコーン油、フルオロカーボン系媒体と
混合して使用することもできる。また、必要により安定
化剤を用いてもよい。該安定化剤としては、ニトロ化合
物、不飽和炭化水素、エポキシ化合物、フェノール化合
物、アルケニルアミン、環状窒素化合物、不飽和アルコ
ール等が挙げられる。その他、目的により各種界面活性
剤を添加してもよい。These media can be used alone or as a mixture thereof. Also, it can be used by mixing with a conventionally used mineral oil-based medium, silicone oil, or fluorocarbon-based medium. Moreover, you may use a stabilizer as needed. Examples of the stabilizer include nitro compounds, unsaturated hydrocarbons, epoxy compounds, phenol compounds, alkenylamines, cyclic nitrogen compounds, unsaturated alcohols and the like. In addition, various surfactants may be added depending on the purpose.
【００１２】本発明の媒体は、分子内にフッ素原子を多
く有する化合物を含むため不燃性もしくは難燃性であ
り、安定性に優れ、従来のＣＦＣ１１３と同程度の浸透
性を有することから媒体として好適に用いることができ
る。本発明の上記含フッ素ケイ素化合物からなる媒体
は、浸透性、安定性が良好で、不燃または難燃性であ
る。また、塩素原子を持たないため、オゾン層の破壊問
題を生じることはなく、分子中に水素原子を含有するの
で地球温暖化効果も小さい。The medium of the present invention is non-combustible or flame-retardant because it contains a compound having a large number of fluorine atoms in the molecule, is excellent in stability, and has the same permeability as that of the conventional CFC113. It can be preferably used. The medium composed of the above-mentioned fluorine-containing silicon compound of the present invention has good permeability and stability, and is nonflammable or flame retardant. Further, since it does not have a chlorine atom, it does not cause the ozone layer depletion problem, and since it contains a hydrogen atom in the molecule, it has a small global warming effect.
【００１３】[0013]
【実施例】以下、本発明の実施例を示すが、本発明はこ
れに限定されるものではない。 実施例１〜１２及び比較例１〜２ 含フッ素系媒体の特性として最も重要である浸透性の指
標として、表面張力がある。表１に本発明の媒体の２３
℃における表面張力、沸点、低温流動性の指標となる融
点および２３℃における粘度を示した。また比較のた
め、ＣＦＣ１１３およびシリコーン化合物であるオクタ
メチルシクロテトラシロキサンの測定値または文献値も
示した。EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited thereto. Examples 1 to 12 and Comparative Examples 1 and 2 Surface tension is the most important index of the permeability of the fluorine-containing medium. Table 1 shows 23 of the medium of the present invention.
The surface tension at ℃, the boiling point, the melting point as an index of low temperature fluidity, and the viscosity at 23 ℃ are shown. For comparison, measured values or literature values of CFC113 and octamethylcyclotetrasiloxane which is a silicone compound are also shown.
【００１４】[0014]
【表１】 [Table 1]
【００１５】表１の結果から、本発明の媒体は表面張力
がＣＦＣ１１３やオクタメチルシクロテトラシロキサン
と同等のレベルであることから浸透性に優れ、潤滑剤、
樹脂改質剤、離型剤、レベリング剤として有用である。
また低粘度で融点が充分に低いことから、オクタメチル
シクロテトラシロキサンに比べ低温流動性が優れ、潤滑
剤、熱媒は特に低温槽の媒体として、また絶縁媒体、不
活性媒体として有用である。 実施例１３〜２１ 本発明の媒体を、水とともに室温で１時間、または８０
℃で４時間振とうし、ＧＣ分析により分解の有無を測定
した。結果はまとめて表２に示した。From the results shown in Table 1, the medium of the present invention has a surface tension equivalent to that of CFC113 or octamethylcyclotetrasiloxane, so that the medium has excellent permeability and a lubricant,
It is useful as a resin modifier, a release agent, and a leveling agent.
Further, since it has a low viscosity and a sufficiently low melting point, it has excellent low-temperature fluidity as compared with octamethylcyclotetrasiloxane, and the lubricant and heat medium are particularly useful as a medium in a low temperature tank, and as an insulating medium and an inert medium. Examples 13 to 21 The medium according to the invention with water at room temperature for 1 hour, or 80
The mixture was shaken at ℃ for 4 hours, and the presence or absence of decomposition was measured by GC analysis. The results are summarized in Table 2.
【００１６】[0016]
【表２】 [Table 2]
【００１７】表２の結果から、本発明の媒体は化学的安
定性に優れ、従って潤滑剤、発泡剤、樹脂改質剤、離型
剤、熱媒、絶縁媒体、不活性媒体、レベリング剤として
有用である。 実施例２２〜２８及び比較例３ 本発明の媒体の引火点をタグ密閉式で測定した。但し８
０℃以下に引火点を持たない化合物についてはさらにク
リーブランド開放式で測定した。また比較のため、シリ
コーン化合物であるオクタメチルシクロテトラシロキサ
ンについても同様に測定した。結果はまとめて表３に示
した。From the results shown in Table 2, the medium of the present invention is excellent in chemical stability and therefore, as a lubricant, a foaming agent, a resin modifier, a release agent, a heat medium, an insulating medium, an inert medium and a leveling agent. It is useful. Examples 22 to 28 and Comparative Example 3 The flash point of the medium of the present invention was measured by the tag closed system. However, 8
The compounds having no flash point below 0 ° C. were further measured by the Cleveland open system. For comparison, the same measurement was performed on octamethylcyclotetrasiloxane, which is a silicone compound. The results are summarized in Table 3.
【００１８】[0018]
【表３】 [Table 3]
【００１９】表３の結果から、本発明の媒体は不燃また
は高引火点液体で、従って潤滑剤、発泡剤、離型剤、熱
媒、絶縁媒体、不活性媒体として用いた場合に安全性に
優れる。 実施例２９〜３４及び比較例４ 各プラスチックのテストピースを、本発明の種々の媒体
に４５℃で１時間浸漬し、重量変化率は室温で２時間放
置後に、寸法変化率は取り出し直後に測定した。また比
較のため、ＣＦＣ１１３についても同様の試験を行っ
た。結果はまとめて表４に示した。From the results shown in Table 3, the medium of the present invention is a non-flammable or high flash point liquid, and therefore is safe when used as a lubricant, a foaming agent, a release agent, a heat medium, an insulating medium or an inert medium. Excel. Examples 29 to 34 and Comparative Example 4 Each plastic test piece was immersed in various media of the present invention at 45 ° C. for 1 hour, the weight change rate was left for 2 hours at room temperature, and the dimensional change rate was measured immediately after removal. did. For comparison, the same test was performed on CFC113. The results are summarized in Table 4.
【００２０】[0020]
【表４】 [Table 4]
【００２１】表４の結果から、本発明の媒体はプラスチ
ックに悪影響を与えることがなく、プラスチック素材と
接触させて用いる潤滑剤、離型剤、熱媒、絶縁媒体、不
活性媒体として特に有用である。From the results shown in Table 4, the medium of the present invention does not adversely affect the plastic, and is particularly useful as a lubricant, a release agent, a heat medium, an insulating medium, and an inert medium used in contact with the plastic material. is there.
【００２２】[0022]
【発明の効果】本発明のフルオロアルコキシ基を有する
含フッ素ケイ素化合物からなる媒体は、浸透性や安定性
が良好で、素材、特にプラスチックに悪影響を与えるこ
とがない。さらに塩素原子を持たないため、オゾン層の
破壊問題を生じることはなく、また水素原子を含有する
ので地球温暖化効果も小さい。従来のＣＦＣやパーフル
オロカーボンと同等に適用できるので極めて価値の高い
ものである。INDUSTRIAL APPLICABILITY The medium composed of the fluorine-containing silicon compound having a fluoroalkoxy group of the present invention has good penetrability and stability and does not adversely affect the material, particularly the plastic. Further, since it has no chlorine atom, it does not cause the ozone layer depletion problem, and since it contains hydrogen atom, it has a small global warming effect. It is extremely valuable because it can be applied in the same way as conventional CFCs and perfluorocarbons.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０９Ｋ 5/00 Ｅ Ｃ１０Ｍ 105/76 ＺＡＢ 9159−4Ｈ // Ｃ１０Ｎ 30:08 40:16 40:36 (71)出願人 000002853 ダイキン工業株式会社 大阪府大阪市北区中崎西２丁目４番12号 梅田センタービル (74)上記３名の代理人 弁理士 小松 秀岳 （外３名 ） (72)発明者 関屋 章 茨城県つくば市東１丁目１番 工業技術院 物質工学工業技術研究所内 (72)発明者 星 信人 東京都文京区本郷２−40−17 本郷若井ビ ル 財団法人 地球環境産業技術研究機構 内 (72)発明者 小林 勉 東京都文京区本郷２−40−17 本郷若井ビ ル 財団法人 地球環境産業技術研究機構 内─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location C09K 5/00 E C10M 105/76 ZAB 9159-4H // C10N 30:08 40:16 40:36 (71) Applicant 000002853 Daikin Industries, Ltd. Umeda Center Building, 2-4-12 Nakazakinishi, Kita-ku, Osaka City, Osaka Prefecture (74) Attorney Hidetaka Komatsu (3rd person outside), Attorney of the above 3 persons (72) Inventor Akira Sekiya 1-1, Higashi Tsukuba-shi, Ibaraki Institute of Industrial Science and Technology, Institute of Materials Engineering (72) Innovator Nobuto Hoshi 2-40-17 Hongo Hongo, Bunkyo-ku, Tokyo Hongo Wakai Building Institute for Global Environmental Technology ( 72) Inventor Tsutomu Kobayashi 2-40-17 Hongo, Bunkyo-ku, Tokyo Hongo Wakai Building Institute for Global Environmental Technology
Claims (9)
に少なくとも１個以上の水素原子を有する、フルオロア
ルコキシ基を有する含フッ素ケイ素化合物からなる媒
体。 【化１】 1. A medium comprising a fluorine-containing silicon compound having a fluoroalkoxy group, which is represented by the following general formula (1) and has at least one hydrogen atom in the molecule. [Chemical 1]
からなる潤滑剤。2. A lubricant comprising the fluorine-containing silicon compound according to claim 1.
からなる発泡剤。3. A foaming agent comprising the fluorine-containing silicon compound according to claim 1.
からなる樹脂改質剤。4. A resin modifier comprising the fluorine-containing silicon compound according to claim 1.
からなる離型剤。5. A mold release agent comprising the fluorine-containing silicon compound according to claim 1.
からなる熱媒。6. A heat transfer medium comprising the fluorine-containing silicon compound according to claim 1.
からなる絶縁媒体。7. An insulating medium comprising the fluorine-containing silicon compound according to claim 1.
からなる不活性媒体。8. An inert medium comprising the fluorine-containing silicon compound according to claim 1.
からなるレベリング剤。9. A leveling agent comprising the fluorine-containing silicon compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6040923A JP2756410B2 (en) | 1994-03-11 | 1994-03-11 | Medium comprising fluorine-containing silicon compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6040923A JP2756410B2 (en) | 1994-03-11 | 1994-03-11 | Medium comprising fluorine-containing silicon compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07247293A true JPH07247293A (en) | 1995-09-26 |
| JP2756410B2 JP2756410B2 (en) | 1998-05-25 |
Family
ID=12594027
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6040923A Expired - Fee Related JP2756410B2 (en) | 1994-03-11 | 1994-03-11 | Medium comprising fluorine-containing silicon compound |
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| Country | Link |
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| JP (1) | JP2756410B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003204073B2 (en) * | 1999-08-16 | 2005-01-06 | Ecolab Inc. | Conveyor Lubricant, Passivation of a Thermoplastic Container to Stress Cracking and Thermoplastic Stress Crack Inhibitor |
| US7745102B2 (en) | 2006-05-26 | 2010-06-29 | Massachusetts Institute Of Technology | Immersion fluids for lithography |
| JP2014534193A (en) * | 2011-10-11 | 2014-12-18 | ヘンケル ユーエス アイピー エルエルシー | Preparation of novel fluoro compounds, process for preparation, and compositions produced therefrom |
| US9873853B2 (en) | 2013-03-11 | 2018-01-23 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
| US9926511B2 (en) | 2005-03-15 | 2018-03-27 | Ecolab Usa Inc. | Lubricant for conveying containers |
| US10260020B2 (en) | 2010-09-24 | 2019-04-16 | Ecolab Usa Inc. | Conveyor lubricants including emulsions and methods employing them |
| US10851325B2 (en) | 2005-03-15 | 2020-12-01 | Ecolab Usa Inc. | Dry lubricant for conveying containers |
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| US3491134A (en) * | 1964-08-03 | 1970-01-20 | Mc Donnell Douglas Corp | Polyfluorinated orthosilicates |
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1994
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|---|---|---|---|---|
| US2892859A (en) * | 1955-05-20 | 1959-06-30 | Research Corp | Fluorine-containing alkoxyalkylsilanes |
| US3491134A (en) * | 1964-08-03 | 1970-01-20 | Mc Donnell Douglas Corp | Polyfluorinated orthosilicates |
| JPH06108096A (en) * | 1992-09-29 | 1994-04-19 | Agency Of Ind Science & Technol | Solvent composition |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003204073B2 (en) * | 1999-08-16 | 2005-01-06 | Ecolab Inc. | Conveyor Lubricant, Passivation of a Thermoplastic Container to Stress Cracking and Thermoplastic Stress Crack Inhibitor |
| US9926511B2 (en) | 2005-03-15 | 2018-03-27 | Ecolab Usa Inc. | Lubricant for conveying containers |
| US10815448B2 (en) | 2005-03-15 | 2020-10-27 | Ecolab Usa Inc. | Lubricant for conveying containers |
| US10851325B2 (en) | 2005-03-15 | 2020-12-01 | Ecolab Usa Inc. | Dry lubricant for conveying containers |
| US7745102B2 (en) | 2006-05-26 | 2010-06-29 | Massachusetts Institute Of Technology | Immersion fluids for lithography |
| US10260020B2 (en) | 2010-09-24 | 2019-04-16 | Ecolab Usa Inc. | Conveyor lubricants including emulsions and methods employing them |
| US10793806B2 (en) | 2010-09-24 | 2020-10-06 | Ecolab Usa Inc. | Conveyor lubricants including emulsions and methods employing them |
| JP2014534193A (en) * | 2011-10-11 | 2014-12-18 | ヘンケル ユーエス アイピー エルエルシー | Preparation of novel fluoro compounds, process for preparation, and compositions produced therefrom |
| US9873853B2 (en) | 2013-03-11 | 2018-01-23 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
| US10316267B2 (en) | 2013-03-11 | 2019-06-11 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
| US10844314B2 (en) | 2013-03-11 | 2020-11-24 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
| US11312919B2 (en) | 2013-03-11 | 2022-04-26 | Ecolab Usa Inc. | Lubrication of transfer plates using an oil or oil in water emulsions |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2756410B2 (en) | 1998-05-25 |
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