JPH04126532A - Nonaqueous surfactant - Google Patents
Nonaqueous surfactantInfo
- Publication number
- JPH04126532A JPH04126532A JP2246190A JP24619090A JPH04126532A JP H04126532 A JPH04126532 A JP H04126532A JP 2246190 A JP2246190 A JP 2246190A JP 24619090 A JP24619090 A JP 24619090A JP H04126532 A JPH04126532 A JP H04126532A
- Authority
- JP
- Japan
- Prior art keywords
- perfluoro
- surfactant
- methyl
- polyfluoroalkyl group
- nonaqueous
- 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
- 239000004094 surface-active agent Substances 0.000 title abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- BAVFAMZQOZGNKO-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-[1,2,2,2-tetrafluoro-1-(1,1,2,2,3,3,3-heptafluoropropoxy)ethyl]benzene Chemical compound FC1=C(F)C(F)=C(C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)=C1F BAVFAMZQOZGNKO-UHFFFAOYSA-N 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 238000002407 reforming Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000001491 aromatic compounds Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 239000000693 micelle Substances 0.000 description 6
- 239000003973 paint Substances 0.000 description 6
- 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
- 238000004140 cleaning Methods 0.000 description 3
- 239000004088 foaming agent Substances 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- -1 perfluoro-1,4-dimethyl-2,5- Dioxaoctylbenzene Chemical compound 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- UHASMEVRHWRZKF-UHFFFAOYSA-N [2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl] 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(=O)OOC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F UHASMEVRHWRZKF-UHFFFAOYSA-N 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CXGONMQFMIYUJR-UHFFFAOYSA-N perfluorododecanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CXGONMQFMIYUJR-UHFFFAOYSA-N 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002525 ultrasonication Methods 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
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、新規な非水系界面活性剤に関し、更に詳しく
は、塗料、インキのレベリング剤、ペイントリムーバー
、レージスト剥離剤、磁気記録材料用潤滑剤及び洗浄用
起泡剤、更にはフッ素系樹脂表面改質剤等に有用な非水
系界面活性剤に関する。Detailed Description of the Invention <Industrial Application Field> The present invention relates to a novel non-aqueous surfactant, and more specifically to a leveling agent for paints and inks, a paint remover, a resist stripping agent, and a lubricant for magnetic recording materials. The present invention relates to a non-aqueous surfactant useful as a cleaning foaming agent, a fluororesin surface modifier, and the like.
〈従来の技術〉
従来フッ素系界面活性剤としては、水溶性界面活性剤と
してペルフルオロドデカン酸及びペルフルオロオクタン
酸等が知られており（「フッ素の化合物」、講談社、１
９７９年）、また非水系界面活性剤として、ペルフルオ
ロアルカンカルボン酸アルキルエステル（例えば、Ｃ，
Ｆ工、 ｃｏｏｃ、。Ｈ３７、石油学会誌、３２巻、２
７７頁、１９８９年）及びヘキサフルオロプロペンオキ
シドのオリゴメル化により得られる、下記構造を有する
アシルフルオリド
（ｎはＯ〜４の整数を示す）とベンゼンとのフリーデル
クラフッ反応により得られる下記構造を有するポリフル
オロアシルベンゼン類
（ｎはＯ〜４の整数を示す）［ジャーナル オブフルオ
リン ケミストリー、２５巻、２４１頁。<Prior art> As conventional fluorine-based surfactants, perfluorododecanoic acid and perfluorooctanoic acid are known as water-soluble surfactants ("Fluorine Compounds", Kodansha, 1).
979), and as non-aqueous surfactants, perfluoroalkane carboxylic acid alkyl esters (e.g., C,
F Engineering, cooc,. H37, Journal of Japan Petroleum Institute, Volume 32, 2
77, 1989) and the following structure obtained by the Friedel-Crach reaction of benzene with an acyl fluoride having the following structure (n represents an integer of O to 4) obtained by oligomerization of hexafluoropropene oxide. (n represents an integer of O to 4) [Journal of Fluorine Chemistry, Vol. 25, p. 241.
１９８４年］等が提案されている。しかしながら下記構
造を有するポリフルオロアルキル基（ｎは整数を示す。1984] etc. have been proposed. However, a polyfluoroalkyl group having the following structure (n represents an integer).
）が直接ベンゼン環に化学結合した非水系界面活性剤に
関しては報告がなされておらず、また表面張力が低く界
面特性の高い非水系界面活性剤の開発が強く望まれてい
るのが現状である。) has been chemically bonded directly to the benzene ring in non-aqueous surfactants, and there is currently a strong desire to develop non-aqueous surfactants with low surface tension and high interfacial properties. .
〈発明が解決しようとする課題〉
本発明の目的は、塗料、インキのレベリング剤、ペイン
トリムーバー、レジスト剥離剤、磁気記録材料用潤滑剤
及び洗浄用起泡剤、更にはフッ素系樹脂表面改質剤等に
有用である非水系ポリフルオロアルキル基含有界面活性
剤を提供することにある。<Problems to be Solved by the Invention> The purpose of the present invention is to provide paints, ink leveling agents, paint removers, resist stripping agents, lubricants for magnetic recording materials, foaming agents for cleaning, and fluororesin surface modification. An object of the present invention is to provide a non-aqueous polyfluoroalkyl group-containing surfactant that is useful for agents and the like.
く課題を解決するための手段〉
本発明によれば、下記一般式（Ｉ）
（式中Ｒは、水素原子又は炭素数１〜４のアルキル基を
示す。またｎは、０〜８の整数を示す）で表わされるポ
リフルオロアルキル基含有芳香族化合物を有効成分とす
る非水系界面活性剤が提供される。According to the present invention, the following general formula (I) (wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and n is an integer of 0 to 8) A non-aqueous surfactant containing a polyfluoroalkyl group-containing aromatic compound represented by the following formula as an active ingredient is provided.
以下本発明を更に詳細に説明する。The present invention will be explained in more detail below.
本発明の非水系界面活性剤において有効成分として用い
られるポリフルオロアルキル基含有芳香族化合物は、下
記一般式（Ｉ）にて表わすことができ、
式中Ｒは、水素原子又は炭素数１〜４のアルキル基を示
す。またｎは、０〜８の整数を示す。この際ｎが９以上
若しくはＲが炭素数５以上のアルキル基の場合には製造
が困難である。前記一般式（Ｉ）で表わされるポリフル
オロアルキル基含有芳香族化合物中の
を具体的に列挙すると、
である。The polyfluoroalkyl group-containing aromatic compound used as an active ingredient in the non-aqueous surfactant of the present invention can be represented by the following general formula (I), where R is a hydrogen atom or has 1 to 4 carbon atoms. represents an alkyl group. Moreover, n represents an integer of 0 to 8. In this case, production is difficult if n is 9 or more or R is an alkyl group having 5 or more carbon atoms. A specific list of the polyfluoroalkyl group-containing aromatic compounds represented by the general formula (I) is as follows.
前記一般式（Ｉ）で表わされるポリフルオロアルキル基
含有芳香族化合物としては、具体的には例えば、ペルフ
ルオロ−１−メチル−２−オキサペンチルベンゼン、ペ
ルフルオロ−１，４−ジメチル−２，５−ジオキサオク
チルベンゼン、ペルフルオロ−１，４，７−ドリメチル
ー２．５．８−トリオキサウンデシルベンゼン、ペルフ
ルオロ−１，４，７，１０−テトラメチ）Ｌ／−２，５
，８゜１１−テトラオキサテトラデシルベンゼン、ペリ
フルオロ−１，４，７，１０，１３−ペンタメチル−２
，５，８，１１，１４−ペンタオキサペンタデシルベン
ゼン、Ｐ−ペルフルオロ−１−メチル−２−オキサペン
チルトルエン、ｐ−ペルフルオロ−１，４−ジメチル−
２，５−ジオキサオクチルトルエン、ｐ−ペルフルオロ
−１，４，７−ドリメチルー２．５．８−トリオキサウ
ンデシルトルエン、ｐ−ペルフルオロ−１，４，７，１
０−テトラメチル−２，５，８，１１−テトラオキサテ
トラデシルトルエン、ｐ−ペルフルオロ−１゜４．７，
１０，１３−ペンタメチル−２，５，８゜１１．１４ペ
ンタオキサ−ペンタデシルトルエン等を好ましく挙げる
ことができる。Specific examples of the polyfluoroalkyl group-containing aromatic compound represented by the general formula (I) include perfluoro-1-methyl-2-oxapentylbenzene, perfluoro-1,4-dimethyl-2,5- Dioxaoctylbenzene, perfluoro-1,4,7-drimethyl-2.5.8-trioxaundecylbenzene, perfluoro-1,4,7,10-tetramethy) L/-2,5
,8゜11-tetraoxatetradecylbenzene, perfluoro-1,4,7,10,13-pentamethyl-2
, 5,8,11,14-pentaoxapentadecylbenzene, P-perfluoro-1-methyl-2-oxapentyltoluene, p-perfluoro-1,4-dimethyl-
2,5-dioxaoctyltoluene, p-perfluoro-1,4,7-drimethyl-2.5.8-trioxaundecyltoluene, p-perfluoro-1,4,7,1
0-tetramethyl-2,5,8,11-tetraoxatetradecyltoluene, p-perfluoro-1°4.7,
Preferred examples include 10,13-pentamethyl-2,5,8°11.14pentaoxa-pentadecyltoluene.
前記一般式（Ｉ）で表わされるポリフルオロアルキル基
含有芳香族化合物を調製するには、ベンゼン又は炭素数
１〜４のアルキルベンゼン類と下記一般式（Ｉｆ）で表
わされる過酸化ポリフルオロアルカノイル
・・・（ＩＩ）
（式中ｎは、０〜８の整数を示す）とを、好ましくは０
〜１００℃にて３０分〜２４時間、反応させるなどして
容易に得ることができる。To prepare the polyfluoroalkyl group-containing aromatic compound represented by the general formula (I), benzene or an alkylbenzene having 1 to 4 carbon atoms and a peroxide polyfluoroalkanoyl represented by the following general formula (If)...・(II) (in the formula, n represents an integer of 0 to 8), preferably 0
It can be easily obtained by reacting at ~100°C for 30 minutes to 24 hours.
本発明の非水系界面活性剤を調製するには、前記一般式
（Ｉ）で表わされるポリフルオロアルキル基含有芳香族
化合物を、例えばベンゼン、トルエン、エチルベンゼン
、プロピルベンゼン、ｐ−キシレン、ｍ−キシレン、０
−キシレン、酢酸エチル、石油エーテル、メチルエチル
ケトン、ケロシン、シクロヘキサン、ｎ−オクタン、ｎ
−ヘキサデカン及びこれらの混合物等から成る群より選
択される有機溶媒に添加し、撹拌あるいは超音波処理を
行なう等して容易に得ることができる。To prepare the non-aqueous surfactant of the present invention, a polyfluoroalkyl group-containing aromatic compound represented by the general formula (I), for example, benzene, toluene, ethylbenzene, propylbenzene, p-xylene, m-xylene, etc. ,0
-xylene, ethyl acetate, petroleum ether, methyl ethyl ketone, kerosene, cyclohexane, n-octane, n
- It can be easily obtained by adding it to an organic solvent selected from the group consisting of hexadecane, mixtures thereof, etc., and subjecting it to stirring or ultrasonication.
前記調製を行なう際における前記ポリフルオロアルキル
基含有芳香族化合物の仕込み量は、有機溶媒全体に対し
て、 Ｉ Ｘ １０−１０−１ｗｒｏＱ ／ Ｑの範囲
とするのが好ましく、この際、前記仕込み量がＩ Ｘ
１０−”■ｏ Ｑ ／ ０未満の場合には界面活性能が
低下し、１ｍｏ１２／Ｑを超えると溶解が困難で作業性
が低下するので好ましくない。また調製温度はであるの
で５〜５０℃の範囲とするのが好ましい。The amount of the polyfluoroalkyl group-containing aromatic compound charged in the preparation is preferably in the range of I is I
If it is less than 10-"■oQ/0, the surfactant ability will decrease, and if it exceeds 1mol12/Q, it will be difficult to dissolve and the workability will decrease, which is not preferable. Also, the preparation temperature is 5 to 50°C. It is preferable to set it as the range of.
更に本発明の非水系界面活性剤は、使用目的に応じて他
の界面活性剤を混合して用いてもよい。Furthermore, the non-aqueous surfactant of the present invention may be used in combination with other surfactants depending on the purpose of use.
〈発明の効果〉
本発明の非水系界面活性剤は、従来の非水系界面活性剤
では見られない高い界面活性を示すので、塗料、インキ
のレベリング剤、ペイントリムーバー、レジスト剥離剤
、磁気記録材料用潤滑剤及び洗浄用起泡剤、更にはフッ
素系樹脂表面改質剤等として有用である。<Effects of the Invention> The non-aqueous surfactant of the present invention exhibits high surface activity not found in conventional non-aqueous surfactants, so it can be used as a leveling agent for paints and inks, paint removers, resist stripping agents, and magnetic recording materials. It is useful as a lubricant for industrial use, a foaming agent for cleaning, and a fluororesin surface modifier.
〈実施例〉
次に、本発明を合成例、実施例及び比較例に基づいて具
体的に説明するが本発明はこれらに限定されるものでは
ない。<Example> Next, the present invention will be specifically explained based on Synthesis Examples, Examples, and Comparative Examples, but the present invention is not limited thereto.
過酸化ペルフルオロ−２−メチル−３−オキサヘキサノ
イル７、９０ｇ （Ｉ２ｍｍｏｆｆｉ）を含む１゜１．
２−トリクロロトリフルオロエタン溶液９０ｇに、ベン
ゼン１．３８ｇ （Ｉ８ｍｍｏＱ）を添加、混合し、窒
素気流下にて、４０℃で、５時間反応を行なった。反応
終了後、反応混合液を５％水酸化ナトリウム水溶液及び
水でそれぞれ２回洗浄を行ない、次いで硫酸マグネシウ
ムで乾燥した後、蒸留を行ないペルフルオロ−１−メチ
ル−２−オキサペンチルベンゼン（ｂｐ１０９〜１１０
℃）を得た。1°1. containing perfluoro-2-methyl-3-oxahexanoyl peroxide 7, 90 g (I2mmoffi).
1.38 g of benzene (I8mmoQ) was added to 90 g of 2-trichlorotrifluoroethane solution, mixed, and reacted at 40° C. for 5 hours under a nitrogen stream. After the reaction was completed, the reaction mixture was washed twice with a 5% aqueous sodium hydroxide solution and water, then dried over magnesium sulfate, and distilled to obtain perfluoro-1-methyl-2-oxapentylbenzene (bp109-110).
°C) was obtained.
失亀鼠よ
ペルフルオロ−１−メチル−２−オキサペンチルベンゼ
ンを、ｍ−キシレンに、表１に示す濃度になるようにそ
れぞれ添加し、室温下にて３０分間撹拌して、各濃度の
非水系界面活性剤をそれぞれ調製した。次いで調製した
非水系界面活性剤２−を表面張力測定用セルに入れ、空
気恒温槽中（２０℃）にて１時間放置し、ウィルベルミ
ー型表面張力計（商品名ｒＳＴ−１型」島津製作所製）
を用いて２０℃恒温下にて表面張力の測定を行なった。Perfluoro-1-methyl-2-oxapentylbenzene was added to m-xylene at the concentrations shown in Table 1, and stirred at room temperature for 30 minutes. Each surfactant was prepared. Next, the prepared non-aqueous surfactant 2- was placed in a cell for measuring surface tension, left in an air constant temperature bath (20°C) for 1 hour, and then placed in a Wilbelmy type surface tension meter (trade name rST-1 type) manufactured by Shimadzu Corporation. )
The surface tension was measured using a constant temperature of 20°C.
結果を表１に示す。The results are shown in Table 1.
表 １
なお、ミセル形成臨界濃度（ｃｍｃ）は、０．５Ｘ１０
−３ｍｏｆｌ／Ｌであった。Table 1 The critical concentration for micelle formation (cmc) is 0.5X10
-3 mofl/L.
迄絞鰹よ
ペルフルオロ−１−メチル−２−オキサペンチルベンゼ
ンを下記構造式で示すペルフルオロ−２−メチル−３−
オキサヘキサノイルベンゼン０−ｃｏｃｐｃｐ、ｏｃ３
Ｆ、 ニ代エタ以外ハ、実施例１と同様に表面張力の測
定を行なった。結果を表２に示す。Perfluoro-1-methyl-2-oxapentylbenzene is expressed by the following structural formula.
Oxahexanoylbenzene 0-cocpcp, oc3
F. The surface tension was measured in the same manner as in Example 1 except for the second layer. The results are shown in Table 2.
なお、ミセル形成臨界濃度（ＣｍＣ）は、１ 、５ Ｘ
１０−２ｍａｉｌ／Ｌであった。The critical concentration for micelle formation (CmC) is 1,5×
It was 10-2 mail/L.
表１及び表２に示す結果から明らかなように、本発明の
非水系界面活性剤は、ペルフルオロ−２−メチル−３−
オキサヘキサノイルベンゼンを用いた界面活性剤に比べ
表面張力が著しく低く、更にはミセル形成臨界濃度（ｃ
ｍ ｃ ）も低く、界面活性の高いものであることが
判明した。As is clear from the results shown in Tables 1 and 2, the nonaqueous surfactant of the present invention is perfluoro-2-methyl-3-
Compared to surfactants using oxahexanoylbenzene, the surface tension is significantly lower, and the critical concentration for micelle formation (c
m c ) was also low, and it was found that the surface activity was high.
失ｌ叢主
ペルフルオロ−１−メチル−２−オキサペンチルベンゼ
ンをｐ−ペルフルオロ−１−メチル−２−オキサペンチ
ルトルエンに代えた以外は実施例１と同様にして表面張
力の測定を行なった。結果を表３に示す。
二（以下余白り、−９、ミ４
：。Surface tension was measured in the same manner as in Example 1, except that p-perfluoro-1-methyl-2-oxapentyltoluene was used instead of perfluoro-1-methyl-2-oxapentylbenzene. The results are shown in Table 3.
2 (margin below, -9, Mi4
:.
′砕Ｓン
表 ３
なお、ミセル形成臨界濃度（ｃｍｃ）は、０．６Ｘ１０
’″）ｍｏｆｆｉ／Ｌであった。Table 3: The critical concentration for micelle formation (cmc) is 0.6X10
''') moffi/L.
失嵐■且
ペルフルオロ−１−メチル−２−オキサペンチルベンゼ
ンをペルフルオロ−１，４−ジメチル−２，５−ジオキ
サオクチルベンゼンに代え、溶媒をｍ−キシレンから酢
酸エチルに代えた以外は実施例１と同様にして表面張力
の測定を行なった。Example except that perfluoro-1-methyl-2-oxapentylbenzene was replaced with perfluoro-1,4-dimethyl-2,5-dioxaoctylbenzene and m-xylene was replaced with ethyl acetate as the solvent. Surface tension was measured in the same manner as in 1.
結果を表４に示す。The results are shown in Table 4.
なお、ミセル形成臨界濃度（ＣｍＣ）は。The critical concentration for micelle formation (CmC) is:
０．３Ｘ１０−”ｍｏｆｌ／Ｌであった。It was 0.3×10-”mofl/L.
失蒼且生
ペルフルオロ−１−メチル−２−オキサペンチルベンゼ
ンをｐ−ペルフルオロ−１，４−ジメチルー２，５−ジ
オキサオクチルトルエンに代えた以外は実施例１と同様
にして表面張力の測定を行なった。結果を表５に示す。Surface tension was measured in the same manner as in Example 1, except that p-perfluoro-1,4-dimethyl-2,5-dioxaoctyltoluene was used instead of perfluoro-1-methyl-2-oxapentylbenzene. I did it. The results are shown in Table 5.
表 ５
なお、ミセル形成臨界濃度（ｃｍｃ）は、０．４Ｘ１０
−３ｍｏＱ／Ｌであった。Table 5 The critical concentration for micelle formation (cmc) is 0.4X10
-3moQ/L.
Claims (1)
示す、またｎは、０〜８の整数を示す）で表わされるポ
リフルオロアルキル基含有芳香族化合物を有効成分とす
る非水系界面活性剤。[Claims] The following general formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, or n represents an integer of 0 to 8) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2246190A JPH04126532A (en) | 1990-09-18 | 1990-09-18 | Nonaqueous surfactant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2246190A JPH04126532A (en) | 1990-09-18 | 1990-09-18 | Nonaqueous surfactant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04126532A true JPH04126532A (en) | 1992-04-27 |
Family
ID=17144857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2246190A Pending JPH04126532A (en) | 1990-09-18 | 1990-09-18 | Nonaqueous surfactant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04126532A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100304384B1 (en) * | 1998-03-23 | 2001-09-24 | 이우에사또시 | Massager |
-
1990
- 1990-09-18 JP JP2246190A patent/JPH04126532A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100304384B1 (en) * | 1998-03-23 | 2001-09-24 | 이우에사또시 | Massager |
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