JPH06108096A - Solvent composition - Google Patents
Solvent compositionInfo
- Publication number
- JPH06108096A JPH06108096A JP26034892A JP26034892A JPH06108096A JP H06108096 A JPH06108096 A JP H06108096A JP 26034892 A JP26034892 A JP 26034892A JP 26034892 A JP26034892 A JP 26034892A JP H06108096 A JPH06108096 A JP H06108096A
- Authority
- JP
- Japan
- Prior art keywords
- group
- solvent composition
- composition according
- compound
- atom
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (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
を有する有機ケイ素化合物を含んでなる溶剤組成物に関
するものである。FIELD OF THE INVENTION The present invention relates to a solvent composition containing an organosilicon compound having a fluoroalkoxy group.
【０００２】[0002]
【従来の技術およびその課題】従来より、ハロゲン化炭
化水素は、プラスチックやゴム製品、電子部品等の洗浄
用溶剤として知られており、それらは塩素原子、または
塩素原子とフッ素原子を有する炭化水素群としての特徴
を有している。これらのハロゲン化炭化水素は、不燃性
で、安定であって、ワックスや油脂類を溶解することが
できることから各種の産業分野に広く使用されている。2. Description of the Related Art Halogenated hydrocarbons have hitherto been known as solvents for cleaning plastics, rubber products, electronic parts, etc. They are hydrocarbons having a chlorine atom or a chlorine atom and a fluorine atom. It has characteristics as a group. These halogenated hydrocarbons are widely used in various industrial fields because they are nonflammable, stable, and can dissolve waxes and fats and oils.
【０００３】たとえば前記塩素原子を有するものとして
は、トリクロロエチレン、テトラクロロエチレンが、ま
た、塩素原子とフッ素原子を有するもの（以下ＣＦＣと
称す）としては、トリフルオロトリクロロエタン（以下
ＣＦＣ１１３と称す）等が知られており、特に後者のＣ
ＦＣ１１３は、低毒性でしかも、プラスチックやゴムな
どの表面を侵食しないので、広く用いられている。For example, trichloroethylene and tetrachloroethylene are known as those having a chlorine atom, and trifluorotrichloroethane (hereinafter referred to as CFC113) and the like are known as those having a chlorine atom and a fluorine atom (hereinafter referred to as CFC). Especially the latter C
FC113 is widely used because it has low toxicity and does not corrode the surface of plastics, rubbers and the like.
【０００４】[0004]
【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ハロゲン化炭化水素は、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から、全廃することが国際
的に決められている。However, in the halogenated hydrocarbon having such excellent characteristics, the chlorine atom, which is one of the constituent elements, acts as a catalyst to destroy the ozone layer surrounding the earth. It is internationally decided to abolish it.
【０００５】このような問題に対処するために、たとえ
ば洗浄溶剤であるＣＦＣ１１３に代わる物質が具体的に
種々検討されているが、未だ有効な代替物が見出されて
いない状況にある。ＣＦＣ１１３や１，１，１−トリク
ロロエタンは全廃されることが国際的に決められている
ことから、これらに代わる新しい洗浄溶剤の開発が不可
欠となっている。In order to deal with such a problem, various substances that replace CFC113, which is a cleaning solvent, have been concretely studied, but an effective alternative has not yet been found. Since it is internationally decided that CFC113 and 1,1,1-trichloroethane will be completely abolished, it is essential to develop a new cleaning solvent to replace them.
【０００６】本発明は、以上の通りの状況に鑑みてなさ
れたものであり、ＣＦＣ１１３等からなるこれまでの洗
浄用溶剤がオゾン層の破壊を引き起こすという欠点を解
消し、オゾン層を破壊せず、洗浄作用に優れた新規な洗
浄溶剤組成物を提供するものである。The present invention has been made in view of the above situation, and solves the drawback that the conventional cleaning solvent composed of CFC113 or the like causes the destruction of the ozone layer and does not destroy the ozone layer. The present invention provides a novel cleaning solvent composition having excellent cleaning action.
【０００７】[0007]
【課題を解決するための手段】本発明者は、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
有する有機ケイ素化合物、すなわち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フルオロアルコキシ
基を有する下記一般式（１）の有機ケイ素化合物が、
１）分子中に塩素を含有しないので、オゾン層を破壊す
る恐れが全く無く、２）油脂類、塵埃などの洗浄効果お
よび熱安定性に優れ、３）従来使用されていたＣＦＣ１
１３と同様の適度な溶解力を持つので、各種の汚れのみ
を選択的に溶解除去し、金属、プラスチック、エラスト
マーなどからなる複合部品を侵さないことを見出し、本
発明を完成するに至った。The inventors of the present invention have conducted extensive studies in view of the state of the art described above, and as a result, have found that an organosilicon compound having a specific structure, that is, a fluorine atom on a carbon atom adjacent to an oxygen atom. An organosilicon compound represented by the following general formula (1) having a fluoroalkoxy group having no
1) Since it does not contain chlorine in the molecule, there is no danger of destroying the ozone layer. 2) Excellent cleaning effect on oils and fats and dust, and thermal stability. 3) Conventional CFC1
Since it has an appropriate dissolving power similar to that of No. 13, it has been found that it selectively dissolves and removes only various kinds of dirt and does not attack composite parts made of metal, plastic, elastomer, etc., and completed the present invention.
【０００８】すなわち、本発明は下記１〜１０の溶剤組
成物等を提供するものである：１ 一般式（１）： Ｒ1 Ｏ−ＳｉＲ2 Ｒ3 Ｒ4 （１） ［式中、Ｒ1 は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２〜８の直鎖又は分枝を有す
るフルオロアルキル基を示し、Ｒ2 、Ｒ3 及びＲ4 はい
ずれも同一または相異なる水素原子、フッ素原子または
１価の有機基を示す。］で表されるフルオロアルコキシ
基を有する有機ケイ素化合物を含んでなる溶剤組成物。That is, the present invention provides the following solvent compositions of 1 to 10 : 1 General formula (1): R 1 O-SiR 2 R 3 R 4 (1) [wherein R 1 Represents a linear or branched fluoroalkyl group having 2 to 8 carbon atoms and having no fluorine atom on the carbon atom adjacent to the oxygen atom, and R 2 , R 3 and R 4 are the same or different from each other. A hydrogen atom, a fluorine atom or a monovalent organic group is shown. ] The solvent composition containing the organosilicon compound which has the fluoroalkoxy group represented by these.
【０００９】２ Ｒ1 は、酸素原子と隣接しない炭素原
子がすべてフッ素原子で置換された基を示す１に記載の
溶剤組成物。 2 R 1 is the solvent composition according to 1 , wherein the carbon atoms not adjacent to the oxygen atom are all substituted with fluorine atoms.
【００１０】３ Ｒ2 、Ｒ3 およびＲ4 が、各々同一ま
たは相異なり水素原子、フッ素原子または炭素原子数１
〜４の直鎖または分枝を有するアルキル基またはアルコ
キシ基である１に記載の溶剤組成物。 3 R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, a fluorine atom or a carbon atom of 1
4. The solvent composition according to 1 , which is a straight-chain or branched alkyl group or alkoxy group of -4.
【００１１】４ Ｒ2 、Ｒ3 およびＲ4 が、同一且つメ
チル基、エチル基、ｎ−プロピル基またはイソプロピル
基である３に記載の溶剤組成物。 4 The solvent composition according to 3 , wherein R 2 , R 3 and R 4 are the same and are a methyl group, an ethyl group, an n-propyl group or an isopropyl group.
【００１２】５ 前記溶剤に、さらに炭化水素化合物、
有機ケイ素化合物、アルコール化合物、ケトン化合物お
よびエステル化合物からなる群から選ばれた１種または
２種以上を、一般式（１）で表されるフルオロアルコキ
シ基を有する有機ケイ素化合物の重量の１〜５０％含有
してなる１〜４のいずれかに記載の溶剤組成物。 5 In addition to the solvent, a hydrocarbon compound,
1 to 50 parts by weight of the organosilicon compound having a fluoroalkoxy group represented by the general formula (1) is selected from the group consisting of organosilicon compounds, alcohol compounds, ketone compounds and ester compounds. %, The solvent composition according to any one of 1 to 4 .
【００１３】６ １〜５のいずれかに記載の溶剤組成物
からなる洗浄剤組成物。 6 A cleaning composition comprising the solvent composition according to any one of 1 to 5.
【００１４】７ １〜５のいずれかに記載の溶剤組成物
からなる水除去剤組成物。 7 A water remover composition comprising the solvent composition according to any one of 1 to 5.
【００１５】８ １〜５のいずれかに記載の溶剤組成物
からなるクリーニング用溶剤組成物。 ９ １〜５のいずれかに記載の溶剤組成物からなる塗料
用溶剤組成物。[0015]8 The solvent composition according to any one of 1 to 5
A cleaning solvent composition comprising: 9 A paint comprising the solvent composition according to any one of 1 to 5
Solvent composition.
【００１６】１０ １〜５のいずれかに記載の溶剤組成
物からなる抽出溶剤組成物。An extraction solvent composition comprising the solvent composition according to any one of 10 1 to 5.
【００１７】本発明において、Ｒ1 で表される酸素原子
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２〜８の直鎖又は分枝を有するフルオロアルキル基と
しては、例えば２−フルオロエチル基、２，２，２−ト
リフルオロエチル基、３−フルオロプロピル基、３，３
−ジフルオロプロピル基、３，３，３−トリフルオロプ
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、
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、１−Ｈ−ヘキサフルオロイ
ソプロピル基、等のフルオロアルキル基が挙げられる。
これらの基のうち、酸素原子と隣接しない炭素原子がす
べてフッ素原子で置換された炭素原子数１〜４の直鎖ま
たは分枝を有する基が好ましい。In the present invention, the linear or branched fluoroalkyl group having 2 to 8 carbon atoms and having no fluorine atom on the carbon atom adjacent to the oxygen atom represented by R 1 is, for example, 2- Fluoroethyl group, 2,2,2-trifluoroethyl group, 3-fluoropropyl group, 3,3
-Difluoropropyl group, 3,3,3-trifluoropropyl group, 2,2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group,
2-trifluoromethyl-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, 1-H A fluoroalkyl group such as a hexafluoroisopropyl group.
Among these groups, a group having a straight or branched chain having 1 to 4 carbon atoms in which all carbon atoms not adjacent to the oxygen atom are substituted with fluorine atoms is preferable.
【００１８】本発明においてＲ2 、Ｒ3 およびＲ4 は、
水素原子、フッ素原子、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、メトキ
シ基、エトキシ基、プロポキシ基、ブトキシ基、イソブ
トキシ基などが挙げられる。この中で、Ｒ2 、Ｒ3 およ
びＲ4 は各々同一または相異なり、水素原子、フッ素原
子、メチル基、エチル基、プロピル基、メトキシ基、エ
トキシ基等が好ましい。特に、溶剤組成物として用いる
場合、Ｒ1 は酸素原子と隣接しない炭素原子がすべてフ
ッ素原子で置換された炭素原子数１〜４の直鎖または分
枝を有する基であって、Ｒ2 、Ｒ3 およびＲ4 が同一で
且つメチル基、エチル基ｎ−プロピル基またはイソプロ
ピル基の時、洗浄性及び熱安定性が良好で、各種の汚れ
のみを選択的に溶解除去し、素材、特にプラスチックに
影響を与えず、沸点が適当な範囲にあるので好ましい。In the present invention, R 2 , R 3 and R 4 are
Examples thereof include a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group and an isobutoxy group. Among them, R 2 , R 3 and R 4 are the same or different and are preferably hydrogen atom, fluorine atom, methyl group, ethyl group, propyl group, methoxy group, ethoxy group and the like. In particular, when used as a solvent composition, R 1 is a straight or branched group having 1 to 4 carbon atoms in which all carbon atoms not adjacent to oxygen atoms are substituted with fluorine atoms, and R 2 and R When 3 and R 4 are the same and are a methyl group, an ethyl group, an n-propyl group or an isopropyl group, the detergency and heat stability are good, and only various stains are selectively dissolved and removed, making them suitable for materials, especially plastics. It has no influence and the boiling point is in an appropriate range, which is preferable.
【００１９】本発明の上記一般式で表されるフルオロア
ルコキシ基を有する有機ケイ素化合物としては、具体的
には： ＊（３，３，３−トリフルオロプロピル）ジメトキシメ
チルシラン、＊（１，１，１，３，３，３−ヘキサフル
オロイソプロポキシ）トリメチルシラン、＊（２−フル
オロエトキシ）トリメチルシラン、＊トリメチル（２，
２，３，３，３−ペンタフルオロプロポキシ）シラン、
＊トリメチル（２，２，３，３−テトラフルオロプロポ
キシ）シラン、＊トリメトキシ（３，３，３−トリフル
オロプロピル）シラン、＊メトキシジメチル（３，３，
３−トリフルオロプロピル）シラン、＊（３，３−ジフ
ルオロプロピル）トリメトキシシラン、＊（３−フルオ
ロプロピル）トリメトキシシラン、＊（２，２，２−ト
リフルオロエトキシ）トリメチルシラン、＊（２，２，
３，３，４，４，４−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、＊（パーフル
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）トリメチルシラン等が挙げられ
る。Specific examples of the organosilicon compound having a fluoroalkoxy group represented by the above general formula of the present invention include: * (3,3,3-trifluoropropyl) dimethoxymethylsilane, * (1,1 , 1,3,3,3-hexafluoroisopropoxy) trimethylsilane, * (2-fluoroethoxy) trimethylsilane, * trimethyl (2,
2,3,3,3-pentafluoropropoxy) silane,
* Trimethyl (2,2,3,3-tetrafluoropropoxy) silane, * Trimethoxy (3,3,3-trifluoropropyl) silane, * Methoxydimethyl (3,3,3
3-trifluoropropyl) silane, * (3,3-difluoropropyl) trimethoxysilane, * (3-fluoropropyl) trimethoxysilane, * (2,2,2-trifluoroethoxy) trimethylsilane, * (2 , 2,
3,3,4,4,4-heptafluorobutoxy) trimethylsilane, * (2,2,3,3,4,4,5,5,5
-Nonafluoropentoxy) trimethylsilane, *
(2,2,3,3,3-pentafluoropropoxy) triethylsilane, * (2,2,3,3,3-pentafluoropropoxy) dimethylethylsilane, * (perfluoro-t-butoxy) trimethylsilane, * [1,1-
Bis (trifluoromethyl) ethoxy] trimethylsilane, * (2,2,3,3-tetrafluoropropoxy)
Examples include trimethylsilane and * (2,2,3,4,4,4-hexafluorobutoxy) trimethylsilane.
【００２０】これらのフルオロアルコキシ基を有する有
機ケイ素化合物は、公知の方法により製造することがで
きる。例えば、含フッ素アルコール（例えば、Ｒ1 Ｏ
Ｈ：Ｒ1 は前記に同じ）をシラザンあるいはクロロシラ
ンと反応させて容易に得られる（例えば、Ｐ．ＹＫＭＡ
Ｎら、Ｊ．Ｏｒｇ．Ｃｈｅｍ．，１１６，１５３−１５
９（１９７６））。これらの化合物は、用途に応じてそ
の他の成分を更に添加混合することができる。例えば、
洗浄剤組成物においては、炭化水素化合物、有機ケイ素
化合物、アルコール化合物、ケトン化合物、エステル化
合物のうち１種または数種を、一般式（１）で表される
フルオロアルコキシ基を有する有機ケイ素化合物の重量
の１〜５０％含有しても良い。該炭化水素化合物として
は、具体的にはペンタン、ヘキサン、ヘプタン、オクタ
ン、シクロヘキサン、ベンゼン、トルエン等の炭素原子
数１〜８の脂肪族アルキル基および芳香族アルキル基が
挙げられる。また、有機ケイ素化合物としては、具体的
にはテトラメチルシラン、テトラエチルシラン、メトキ
シトリメチルシラン、エトキシトリメチルシラン、トリ
エチルシラン、ジメチルエトキシシラン、エチルトリメ
チルシラン等が挙げられる。アルコール化合物として
は、メタノール、エタノール、プロパノール、ブタノー
ルなどの炭素原子数１〜４のアルコールが挙げられる。
ケトン化合物としては、プロパノン、ブタノン、２−ペ
ンタノン、３−ペンタノンなどが挙げられる。エステル
化合物としては、カルボン酸エステル、例えばギ酸エス
テル、酢酸エステルなどが挙げられる。The organosilicon compound having these fluoroalkoxy groups can be produced by a known method. For example, a fluorine-containing alcohol (for example, R 1 O
It is easily obtained by reacting H: R 1 with silazane or chlorosilane (for example, P.YKMA).
N., et al. Org. Chem. , 116 , 153-15
9 (1976)). Other components may be further added to and mixed with these compounds depending on the application. For example,
In the detergent composition, one or more of a hydrocarbon compound, an organosilicon compound, an alcohol compound, a ketone compound, and an ester compound is used as an organosilicon compound having a fluoroalkoxy group represented by the general formula (1). You may contain 1 to 50% of a weight. Specific examples of the hydrocarbon compound include an aliphatic alkyl group having 1 to 8 carbon atoms and an aromatic alkyl group such as pentane, hexane, heptane, octane, cyclohexane, benzene and toluene. Specific examples of the organosilicon compound include tetramethylsilane, tetraethylsilane, methoxytrimethylsilane, ethoxytrimethylsilane, triethylsilane, dimethylethoxysilane, and ethyltrimethylsilane. Examples of the alcohol compound include alcohols having 1 to 4 carbon atoms such as methanol, ethanol, propanol and butanol.
Examples of the ketone compound include propanone, butanone, 2-pentanone and 3-pentanone. Examples of the ester compound include carboxylic acid esters such as formic acid ester and acetic acid ester.
【００２１】また、本発明化合物は、通常の使用におい
て熱安定性は良好であるが、必要により安定化剤を用い
ても良い。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、不飽和アルコールが挙げ
られる。その他、界面活性剤を添加しても良い。The compound of the present invention has good thermal stability in normal use, but a stabilizer may be used if necessary. Examples of the stabilizer include nitro compounds, unsaturated hydrocarbons, epoxy compounds, phenol compounds, alkenylamines, cyclic nitrogen compounds and unsaturated alcohols. In addition, a surfactant may be added.
【００２２】本発明にかかる上記化合物の用途として
は、溶剤組成物の他、発泡剤、プロペラント、冷媒など
が挙げられ、特にこれらの化合物は従来のＣＦＣ１１３
と同程度の溶解力を有するため、溶剤組成物として用い
るのが好適である。溶剤組成物の具体的な用途として
は、洗浄剤組成物、水除去剤組成物、ドライクリーニン
グ溶剤組成物、塗料用溶剤組成物、抽出剤組成物が挙げ
られる。洗浄剤組成物は、フラックス、グリース、油、
ワックス、インキ等をガラス、セラミックス、プラスチ
ック、ゴム、金属性各種物品、特にＩＣ部品、電気機
器、精密機械、光学レンズ等の表面から取り除くために
用いられる。また、水除去剤組成物は前記物品を水洗浄
した後に、水を表面から取り除くために用いられる。洗
浄方法としては、手拭き、浸漬、スプレー、揺動、超音
波洗浄、蒸気洗浄等を採用すれば良い。Applications of the above-mentioned compounds according to the present invention include a solvent composition, a foaming agent, a propellant, a refrigerant and the like. In particular, these compounds are conventional CFC113.
Since it has a dissolving power of the same level as, it is suitable for use as a solvent composition. Specific applications of the solvent composition include a cleaning composition, a water removing composition, a dry cleaning solvent composition, a coating solvent composition, and an extracting composition. The cleaning composition is a flux, grease, oil,
It is used to remove wax, ink and the like from the surfaces of glass, ceramics, plastics, rubber and various metallic articles, especially IC parts, electric devices, precision machines, optical lenses and the like. Further, the water removing agent composition is used for removing water from the surface after washing the article with water. As a cleaning method, hand wiping, dipping, spraying, shaking, ultrasonic cleaning, steam cleaning or the like may be adopted.
【００２３】本発明の上記有機ケイ素化合物は洗浄性及
び熱安定性が良好で、各種汚れのみを選択的に溶解し、
素材特にプラスチックに与える影響も少ない。また、塩
素原子を持たないため、オゾン層破壊問題を生じること
はない。さらに熱分解温度が高いので、熱安定性が特に
要求される気相のハンダ付用途にも適用できる。The above-mentioned organosilicon compound of the present invention has good detergency and heat stability and selectively dissolves only various stains.
It has little effect on materials, especially on plastic. Further, since it has no chlorine atom, it does not cause the ozone layer depletion problem. Furthermore, since the thermal decomposition temperature is high, it can be applied to vapor phase soldering applications where thermal stability is particularly required.
【００２４】以下に、本発明に用いる化合物の製造例
と、本発明の実施例を示す。The production examples of the compounds used in the present invention and the examples of the present invention are shown below.
【００２５】[0025]
【製造例１】 ＊２，２，２−トリフルオロエトキシトリメチルシラン
の製造 ２，２，２−トリフルオロエタノール６０．０ｇ（０．
６モル）とヘキサメチルジシラザン４８．４ｇ（０．３
モル）を室温で混合し、徐々に加熱、さらに１１時間加
熱還流した。反応液を、精留管を付けて蒸留して標記化
合物を得た。収量８２．５ｇ（収率８０％）。沸点８１
〜８１．５℃。[Production Example 1] * Production of 2,2,2-trifluoroethoxytrimethylsilane 60.0 g of 2,2,2-trifluoroethanol (0.
6 mol) and 48.4 g of hexamethyldisilazane (0.3
Mol) were mixed at room temperature, gradually heated, and further heated and refluxed for 11 hours. The reaction solution was distilled with a rectification tube to obtain the title compound. Yield 82.5 g (80% yield). Boiling point 81
~ 81.5 ° C.
【００２６】[0026]
【製造例２】 ＊２，２，３，３，３−ペンタフルオロプロポキシトリ
メチルシランの製造 ２，２，３，３，３−ペンタフルオロプロパノール６
０．０ｇ（０．４モル）とヘキサメチルジシラザン３
２．３ｇ（０．２モル）を室温で混合し、徐々に加熱、
さらに１１時間加熱還流した。反応液を蒸留後、さらに
精留管を付けて蒸留して標記化合物を得た。収量５４．
０ｇ（収率６１％）。沸点９６℃。Production Example 2 * Production of 2,2,3,3,3-pentafluoropropoxytrimethylsilane 2,2,3,3,3-pentafluoropropanol 6
0.0 g (0.4 mol) and hexamethyldisilazane 3
2.3 g (0.2 mol) are mixed at room temperature and gradually heated,
The mixture was heated under reflux for another 11 hours. After the reaction solution was distilled, it was further distilled by attaching a rectification tube to obtain the title compound. Yield 54.
0 g (61% yield). Boiling point 96 ° C.
【００２７】[0027]
【製造例３】 ＊１−Ｈ−ヘキサフルオロイソプロポキシトリメチルシ
ランの製造 １，１，１，３，３，３−ヘキサフルオロ−２−プロパ
ノール６７．２ｇ（０．４モル）とヘキサメチルジシラ
ザン３２．３ｇ（０．２モル）を室温で混合し、徐々に
加熱、さらに３０分間加熱還流した。反応液を蒸留後、
さらに精留管を付けて蒸留して標記化合物を得た。収量
７９．１ｇ（収率８２％）。沸点９０℃[Production Example 3] Production of 1-H-hexafluoroisopropoxytrimethylsilane 67.2 g (0.4 mol) of 1,1,1,3,3,3-hexafluoro-2-propanol and hexamethyldisilazane 32.3 g (0.2 mol) were mixed at room temperature, gradually heated, and further heated and refluxed for 30 minutes. After distilling the reaction solution,
Further, distillation was carried out with a rectification tube to obtain the title compound. Yield 79.1 g (yield 82%). Boiling point 90 ℃
【００２８】。..
【実施例１〜３および比較例１〜２】空気中、温度５０
０℃で１時間加熱したＳＵＳ−３１６製容器に試料を５
０torr注入する。その容器を２時間かけて室温から５０
０℃まで昇温させ、圧力−温度が直線からずれ始めた点
を熱分解開始温度として試料の耐熱性を調べた。Examples 1 to 3 and Comparative Examples 1 to 2 In air, temperature 50
Samples were placed in a SUS-316 container heated at 0 ° C for 1 hour.
Inject 0 torr. Allow the container to cool from room temperature to 50
The temperature was raised to 0 ° C., and the point at which the pressure-temperature began to deviate from the straight line was used as the thermal decomposition start temperature to examine the heat resistance of the sample.
【００２９】結果を一括して表１に示す。The results are collectively shown in Table 1.
【００３０】なお、比較のため、酸素原子と隣接した炭
素原子上にフッ素原子を持つ化合物およびＣＦＣ１１３
の熱分解開始温度を併記した。なお、表中、Ｍｅはメチ
ル基を示す。For comparison, a compound having a fluorine atom on a carbon atom adjacent to an oxygen atom and CFC113
The thermal decomposition start temperature of is also shown. In the table, Me represents a methyl group.
【００３１】[0031]
【表１】 [Table 1]
【００３２】表１の結果から、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本発明の化合物は、比較
例１の炭素原子上にフッ素原子を持つ化合物および比較
例２のＣＦＣ１１３に比較して優れた熱安定性を有する
ことが明らかである。From the results shown in Table 1, the compound of the present invention having no fluorine atom on the carbon atom adjacent to the oxygen atom was compared with the compound having a fluorine atom on the carbon atom of Comparative Example 1 and CFC113 of Comparative Example 2. It is clear that it has excellent thermal stability.
【００３３】[0033]
【実施例４〜１０および比較例３】ＳＵＳ−３０４のテ
ストピースを機械油（日本石油製ＣＱ−３０）中に浸漬
した後、本発明の種々の洗浄剤組成物に２５℃で５分間
浸漬した。目視によって、機械油の除去された程度を観
察した。Examples 4 to 10 and Comparative Example 3 A test piece of SUS-304 was dipped in a machine oil (CQ-30 manufactured by Nippon Oil Co., Ltd.) and then dipped in various detergent compositions of the present invention at 25 ° C. for 5 minutes. did. The extent to which the mechanical oil was removed was visually observed.
【００３４】結果を一括して表２に示す。なお、比較の
ため、従来の機械油の洗浄剤であるＣＦＣ１１３を溶剤
とした場合を併記した。The results are collectively shown in Table 2. For comparison, a case where CFC113, which is a conventional cleaning agent for machine oil, is used as a solvent is also shown.
【００３５】[0035]
【表２】 [Table 2]
【００３６】ただし、表２中：“○”は、肉眼で見える
洗浄残りがないことを示す。However, in Table 2, "◯" indicates that there is no uncleaned residue that is visible to the naked eye.
【００３７】“×”は、肉眼で見える洗浄残りがあるこ
とを示す。"X" indicates that there is a visible wash residue.
【００３８】表２の結果から、本発明の溶剤組成物は、
従来使用されていたＣＦＣ１１３と同等程度の洗浄力を
有することが明らかとなった。From the results shown in Table 2, the solvent composition of the present invention is
It has become clear that it has a cleaning power equivalent to that of the CFC 113 used conventionally.
【００３９】[0039]
【発明の効果】本発明のフルオロアルコキシ基を有する
有機ケイ素化合物は、溶剤組成物としての洗浄性及び熱
安定性が良好で、素材特にプラスチックに悪影響を与え
ず、さらに塩素原子を持たないため、オゾン層破壊問題
を生じることはなく、従来のＣＦＣ系溶剤と同じ使い方
ができ、既存装置の大幅な変更を必要とせず、そのまま
適用できるなど極めて価値の高いものである。Industrial Applicability The organosilicon compound having a fluoroalkoxy group of the present invention has good detergency and thermal stability as a solvent composition, does not adversely affect the material, particularly the plastic, and has no chlorine atom. It does not cause ozone layer depletion problems, can be used in the same way as conventional CFC-based solvents, does not require major changes to existing equipment, and can be applied as is, which is extremely valuable.
【００４０】[0040]
───────────────────────────────────────────────────── フロントページの続き (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 (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 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Tsutomu Kobayashi 2-40-17 Hongo, Bunkyo-ku, Tokyo Hongo Wakai Building within the Institute for Global Environmental Technology (72) Innovator Nobuto Hoshi Hongo, Bunkyo-ku, Tokyo 2 −40−17 Hongo Wakai Building, Research Institute for Global Environmental Technology
Claims (10)
原子を持たない炭素原子数２〜８の直鎖又は分枝を有す
るフルオロアルキル基を示し、Ｒ2 、Ｒ3 及びＲ4 はい
ずれも同一または相異なる水素原子、フッ素原子または
１価の有機基を示す。］で表されるフルオロアルコキシ
基を有する有機ケイ素化合物を含んでなる溶剤組成物。1. A compound represented by the general formula (1): R 1 O—SiR 2 R 3 R 4 (1) [wherein R 1 is 2 to 2 carbon atoms having no fluorine atom on a carbon atom adjacent to an oxygen atom]. 8 is a linear or branched fluoroalkyl group, and R 2 , R 3 and R 4 are the same or different hydrogen atoms, fluorine atoms or monovalent organic groups. ] The solvent composition containing the organosilicon compound which has the fluoroalkoxy group represented by these.
すべてフッ素原子で置換された基を示す請求項１に記載
の溶剤組成物。2. The solvent composition according to claim 1, wherein R 1 represents a group in which all carbon atoms not adjacent to oxygen atoms are substituted with fluorine atoms.
相異なり水素原子、フッ素原子または炭素原子数１〜４
の直鎖または分枝を有するアルキル基またはアルコキシ
基である請求項１に記載の溶剤組成物。3. R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, a fluorine atom or 1 to 4 carbon atoms.
The solvent composition according to claim 1, which is a linear or branched alkyl group or alkoxy group.
基、エチル基、ｎ−プロピル基またはイソプロピル基で
ある請求項３に記載の溶剤組成物。4. The solvent composition according to claim 3, wherein R 2 , R 3 and R 4 are the same and are a methyl group, an ethyl group, an n-propyl group or an isopropyl group.
ケイ素化合物、アルコール化合物、ケトン化合物および
エステル化合物からなる群から選ばれた１種または２種
以上を、一般式（１）で表されるフルオロアルコキシ基
を有する有機ケイ素化合物の重量の１〜５０％含有して
なる請求項１〜４のいずれかに記載の溶剤組成物。5. One or more selected from the group consisting of a hydrocarbon compound, an organosilicon compound, an alcohol compound, a ketone compound and an ester compound is further represented by the general formula (1) in the solvent. The solvent composition according to claim 1, which comprises 1 to 50% by weight of the organosilicon compound having a fluoroalkoxy group.
物からなる洗浄剤組成物。6. A detergent composition comprising the solvent composition according to claim 1.
物からなる水除去剤組成物。7. A water remover composition comprising the solvent composition according to claim 1.
物からなるクリーニング用溶剤組成物。8. A cleaning solvent composition comprising the solvent composition according to claim 1.
物からなる塗料用溶剤組成物。9. A solvent composition for coating, which comprises the solvent composition according to claim 1.
成物からなる抽出溶剤組成物。10. An extraction solvent composition comprising the solvent composition according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26034892A JP2660313B2 (en) | 1992-09-29 | 1992-09-29 | Solvent composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26034892A JP2660313B2 (en) | 1992-09-29 | 1992-09-29 | Solvent composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06108096A true JPH06108096A (en) | 1994-04-19 |
| JP2660313B2 JP2660313B2 (en) | 1997-10-08 |
Family
ID=17346724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26034892A Expired - Lifetime JP2660313B2 (en) | 1992-09-29 | 1992-09-29 | Solvent composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2660313B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07247293A (en) * | 1994-03-11 | 1995-09-26 | Agency Of Ind Science & Technol | Medium of fluorine-containing silicon compound |
| WO2007126194A1 (en) * | 2006-05-02 | 2007-11-08 | Korea Institute Of Science And Technology | Method of preparing fluorinated alkoxytrialkylsilanes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4820207B2 (en) | 2005-08-31 | 2011-11-24 | 本田技研工業株式会社 | Scooter type vehicle power unit suspension system |
-
1992
- 1992-09-29 JP JP26034892A patent/JP2660313B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07247293A (en) * | 1994-03-11 | 1995-09-26 | Agency Of Ind Science & Technol | Medium of fluorine-containing silicon compound |
| WO2007126194A1 (en) * | 2006-05-02 | 2007-11-08 | Korea Institute Of Science And Technology | Method of preparing fluorinated alkoxytrialkylsilanes |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2660313B2 (en) | 1997-10-08 |
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