JPH026448A - Fluorine-contaiing amide compound - Google Patents
Fluorine-contaiing amide compoundInfo
- Publication number
- JPH026448A JPH026448A JP15744988A JP15744988A JPH026448A JP H026448 A JPH026448 A JP H026448A JP 15744988 A JP15744988 A JP 15744988A JP 15744988 A JP15744988 A JP 15744988A JP H026448 A JPH026448 A JP H026448A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- formula
- amide compound
- acid
- compound expressed
- 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
Links
- -1 amide compound Chemical class 0.000 title claims abstract description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
- 239000011737 fluorine Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 9
- 239000002184 metal Substances 0.000 abstract description 9
- 229920000642 polymer Polymers 0.000 abstract description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003607 modifier Substances 0.000 abstract description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003921 oil Substances 0.000 abstract description 3
- 230000002940 repellent Effects 0.000 abstract description 3
- 239000005871 repellent Substances 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000000463 material Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
この発明は特に高分子の表面改質剤で、就中、金属と接
する高分子表面の摺動剤として有用な含フツ素アミド化
合物に関する。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application This invention relates to a fluorine-containing amide compound that is particularly useful as a surface modifier for polymers, and more particularly as a sliding agent for polymer surfaces that come into contact with metals.
従来の技術
従来から、高分子表面の摺動剤としてはステアリン酸等
の脂肪酸が多用されているが、金属と高分子との摺動面
においては、この種の脂肪酸は金属の腐食を誘発する可
能性が高いので不適当である。Conventional technology Traditionally, fatty acids such as stearic acid have been frequently used as sliding agents on polymer surfaces, but on sliding surfaces between metals and polymers, these types of fatty acids induce corrosion of metals. It is inappropriate because the possibility is high.
発明が解決しようとする課題
この発明は、金属と接する高分子表面への摺動性付与を
含む高分子表面改質剤として有用なだけでなく、金属表
面処理剤や撥水撥油剤等としても汎用し得る新規な含フ
ツ素アミド化合物を提供するためになされたものである
。Problems to be Solved by the Invention This invention is useful not only as a polymer surface modifier that imparts sliding properties to polymer surfaces that come into contact with metals, but also as a metal surface treatment agent, water and oil repellent, etc. This was done in order to provide a novel fluorine-containing amide compound that can be used for general purposes.
即ち本発明は、一般式［Ｉ］：
（式中、Ｒ１およびＲ２はそれぞれ独立に水素原子また
は分枝鎖を有することもある炭素原子数１〜３０のアル
キル基を示し、ｎは１または２の数を示す。）
で表わされる含フツ素アミド化合物に関する。That is, the present invention relates to the general formula [I]: (wherein R1 and R2 each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms which may have a branched chain, and n is 1 or 2. The number of fluorine-containing amide compounds represented by
式［１］において、Ｒ３およびＲ２はそれぞれ独立して
水素原子または分枝鎖を有することもある炭素原子数ｌ
〜３０、好ましくは８〜２２のアルキル基を示し、口は
Ｉまたは２の数を示す。In formula [1], R3 and R2 each independently have a hydrogen atom or a carbon atom number l that may have a branched chain.
-30, preferably 8-22 alkyl groups, and the mouth indicates the number I or 2.
特に好適な含フン素化合物は次式［Ｉａ］および［■ｂ
１で表わされる化合物である（式中、Ｒ，およびＲ２は
前記と同意義である）：
ペルフルオロノネニルオキシ基として特に好ましいもの
は以下の構造式（ａ）で表わされるものである：
ＣＦ。Particularly suitable fluorine-containing compounds are the following formulas [Ia] and [■b
A particularly preferred perfluorononenyloxy group is one represented by the following structural formula (a): CF.
一般式［１］で表わされる含フツ素アミド化合物の製造
方法は特に限定的ではないが、簡便な方法は、ペルフル
オロノネニルオキシ基を有するベンゼンモノカルボン酸
［例えば、４−（ベルフルオロノ不ニルオキン）安息香
酸等］もしくはベンゼンジカルボン酸［例えは、５−（
ペルフルオロノネニルオキ／）イソフタル酸等１を出発
原料とし、これに塩化チオニル等を反応させて酸塩化物
を誘導した後、各種のアミンを用いてアミド化する方法
である。The method for producing the fluorine-containing amide compound represented by the general formula [1] is not particularly limited, but a simple method is to use benzene monocarboxylic acid having a perfluorononenyloxy group [e.g., 4-(perfluoronononyloxy)] benzoic acid, etc.] or benzenedicarboxylic acid [e.g., 5-(
This method uses perfluorononenyloki/)isophthalic acid 1 as a starting material, reacts it with thionyl chloride, etc. to derive an acid chloride, and then amidates it using various amines.
以下、本発明を実施例によって説明する。Hereinafter, the present invention will be explained by examples.
実施例１
冷却管、滴下漏斗、温度計および攪拌装置を備えた４つ
ロフラスコ内に４−（ベルフルオロノネニルオキン）ペ
ンゾイルクロリＦ ｌ １７．５ｇ（０。Example 1 17.5 g (0.0 g) of 4-(berfluorononenyloquine)penzoylchlori Fl were placed in a four-bottle flask equipped with a condenser, dropping funnel, thermometer and stirrer.
２０モル）および無水ジエチルエーテル３００ｍ＋２を
入れて充分に攪拌混合した後、該フラスコを氷−水浴を
用いて冷却し、反応系の温度が急上昇しない条件下にお
いて、ｎ−オクチルアミン２５．５５ｇ（０，２０モル
）、トリエチルアミン２２．２７ｇ（０，２２モル）お
よび無水ジエチルエーテル２５０ｍ１２から成る混合溶
液を３０分間かけて徐々に滴下した。After thoroughly stirring and mixing, the flask was cooled using an ice-water bath, and 25.55 g of n-octylamine (0 .
滴下終了後、約０〜２０°Ｃにおいて攪拌をさらに１２
時時間待した。反応混合物から白色沈殿物（トリエチル
アミン塩酸塩）を吸引濾過によって濾別し、濾液を水道
水および希塩酸を用いて洗浄し、次いで無水硫酸マグネ
シウムを用いて乾燥した後、濃縮し、粗生成物をクロロ
ホルムを溶離剤とする／リカゲルカラムクロマトグラフ
ィー処理に付すことによって含フツ素アミド化合物ｌを
１１１゜６４ｇ得た（収率：８２％）。After the addition is complete, continue stirring at approximately 0 to 20°C for an additional 12 hours.
I waited for hours. A white precipitate (triethylamine hydrochloride) was filtered off from the reaction mixture by suction filtration, the filtrate was washed with tap water and dilute hydrochloric acid, then dried over anhydrous magnesium sulfate, concentrated, and the crude product was dissolved in chloroform. By subjecting the product to silica gel column chromatography using as an eluent, 111.64 g of fluorine-containing amide compound 1 was obtained (yield: 82%).
得られた生成物の物性を以下の表−■に示す。The physical properties of the obtained product are shown in Table 1 below.
実施例２〜７
実施例１の手順に準拠して含フツ素アミド化合物２〜７
を調製した。Examples 2 to 7 Fluorine-containing amide compounds 2 to 7 were prepared according to the procedure of Example 1.
was prepared.
これらの化合物の物性を以下の表−１に示す。The physical properties of these compounds are shown in Table 1 below.
（以下、余白）
発明の効果
本発明による含フツ素アミド化合物は、含フッ素基を有
するので優れた摺動性、撥水撥油性、耐熱性および耐薬
品性等の特性を具備し、また、アミド結合を有するので
極性が高く、安定であり、さらに、アセトン等の常套の
有機溶媒に対する溶解度も高いので利用し易い。(Hereinafter, blank spaces) Effects of the Invention The fluorine-containing amide compound according to the present invention has a fluorine-containing group, so it has properties such as excellent sliding properties, water and oil repellency, heat resistance, and chemical resistance. Since it has an amide bond, it is highly polar and stable, and furthermore, it has high solubility in common organic solvents such as acetone, so it is easy to use.
従って、本発明による含フツ素アミド化合物は、金属と
接する高分子表面への摺動性付与を含む高分子表面改質
剤として有用なだけでなく、金属表面旭理剤、撥水撥油
剤等としても汎用し得る。Therefore, the fluorine-containing amide compound according to the present invention is not only useful as a polymer surface modifier that imparts sliding properties to polymer surfaces in contact with metals, but also as a metal surface coating agent, water and oil repellent, etc. It can also be used for general purposes.
Claims (1)
または分枝鎖を有することもある炭素原子数１〜３０の
アルキル基を示し、ｎは１または２の数を示す。） で表わされる含フッ素アミド化合物。[Claims] 1. General formula [I]: ▲Mathematical formula, chemical formula, table, etc.▼[I] (In the formula, R_1 and R_2 each independently represent a hydrogen atom or a carbon that may have a branched chain. An alkyl group having 1 to 30 atoms, and n is 1 or 2.) A fluorine-containing amide compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63157449A JP2540602B2 (en) | 1988-06-25 | 1988-06-25 | Fluorine-containing amide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63157449A JP2540602B2 (en) | 1988-06-25 | 1988-06-25 | Fluorine-containing amide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH026448A true JPH026448A (en) | 1990-01-10 |
| JP2540602B2 JP2540602B2 (en) | 1996-10-09 |
Family
ID=15649903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63157449A Expired - Fee Related JP2540602B2 (en) | 1988-06-25 | 1988-06-25 | Fluorine-containing amide compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2540602B2 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111084A (en) * | 1974-07-17 | 1976-01-28 | Shinnitsuto Kagaku Kk | Ganfutsusokaimenkatsuseizai oyobi sonoseiho |
| JPS5925359A (en) * | 1983-03-11 | 1984-02-09 | Neos Co Ltd | Preparation of alkylene oxide adduct of fluorine-containing compound |
| JPS5925358A (en) * | 1983-03-11 | 1984-02-09 | Neos Co Ltd | Preparation of fluorine-containing amino compound |
-
1988
- 1988-06-25 JP JP63157449A patent/JP2540602B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5111084A (en) * | 1974-07-17 | 1976-01-28 | Shinnitsuto Kagaku Kk | Ganfutsusokaimenkatsuseizai oyobi sonoseiho |
| JPS5925359A (en) * | 1983-03-11 | 1984-02-09 | Neos Co Ltd | Preparation of alkylene oxide adduct of fluorine-containing compound |
| JPS5925358A (en) * | 1983-03-11 | 1984-02-09 | Neos Co Ltd | Preparation of fluorine-containing amino compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2540602B2 (en) | 1996-10-09 |
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