JP2540602B2 - Fluorine-containing amide compound - Google Patents

Fluorine-containing amide compound

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Publication number
JP2540602B2
JP2540602B2 JP63157449A JP15744988A JP2540602B2 JP 2540602 B2 JP2540602 B2 JP 2540602B2 JP 63157449 A JP63157449 A JP 63157449A JP 15744988 A JP15744988 A JP 15744988A JP 2540602 B2 JP2540602 B2 JP 2540602B2
Authority
JP
Japan
Prior art keywords
fluorine
amide compound
containing amide
polymer
formula
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
Application number
JP63157449A
Other languages
Japanese (ja)
Other versions
JPH026448A (en
Inventor
伸之 中山
興二 矢野
仁也 佛願
信彦 立入
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Neos Co Ltd
Original Assignee
Neos Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Neos Co Ltd filed Critical Neos Co Ltd
Priority to JP63157449A priority Critical patent/JP2540602B2/en
Publication of JPH026448A publication Critical patent/JPH026448A/en
Application granted granted Critical
Publication of JP2540602B2 publication Critical patent/JP2540602B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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ッ素アミド
化合物に関する。
Description: FIELD OF THE INVENTION The present invention relates to a fluorine-containing amide compound which is a surface modifier of a polymer and is particularly useful as a sliding agent for the surface of a polymer in contact with a metal.

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。
BACKGROUND ART Conventionally, fatty acids such as stearic acid have been widely used as sliding agents for polymer surfaces, but on the sliding surface between metal and polymer, this type of fatty acid induces metal corrosion. It is unsuitable because it is likely.

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
フッ素アミド化合物を提供するためになされたものであ
る。
DISCLOSURE OF THE INVENTION The present invention is not only useful as a polymer surface modifier including imparting slidability to a polymer surface in contact with a metal, but also as a metal surface treatment agent, a water / oil repellent agent, or the like. This is done in order to provide a novel fluorine-containing amide compound that can be used widely.

課題を解決するための手段 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8〜30のアルキル
基を示し(但し、R1およびR2は同時には水素原子を示さ
ない)、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に関する。
Means for Solving the Problems That is, the present invention provides a compound represented by the general formula [I]: (In the formula, R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 8 to 30 carbon atoms which may have a branched chain (provided that R 1 and R 2 represent hydrogen atoms at the same time). No), and n represents a number of 1 or 2.).

式[I]において、R1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8〜
30、好ましくは8〜22のアルキル基を示し(但し、R1
よびR2は同時には水素原子を示さない)、nは1または
2の数を示す。
In the formula [I], R 1 and R 2 are each independently a hydrogen atom or a carbon atom having a branched chain of 8 to 8
30, preferably 8 to 22 alkyl groups (provided that R 1 and R 2 do not simultaneously represent hydrogen atoms), and n represents a number of 1 or 2.

特に好適な含フッ素化合物は次式[I a]および[I
b]で表わされる化合物である(式中、R1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: 一般式[I]で表わされる含フッ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−(ペルフルオロノネニルオキシ)安息
香酸等]もしくはベンゼンジカルボン酸[例えば、5−
(ペルフルオロノネニルオキシ)イソフタル酸等]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。
Particularly suitable fluorine-containing compounds are represented by the following formulas [I a] and [I a
b] is a compound represented by the formula (wherein R 1 and R 2 are as defined above): Particularly preferred perfluorononenyloxy groups are those represented by the following structural formula (a): The method for producing the fluorine-containing amide compound represented by the general formula [I] is not particularly limited, but a simple method is a benzenemonocarboxylic acid having a perfluorononenyloxy group [for example, 4- (perfluorononenyloxy) Benzoic acid or the like] or benzenedicarboxylic acid [eg, 5-
(Perfluorononenyloxy) isophthalic acid and the like] is used as a starting material, and thionyl chloride and the like are reacted therewith to induce an acid chloride, and then amidated with 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 described with reference to examples.

実施例1 冷却管、滴下漏斗、温度計および撹拌装置を備えた4
つ口フラスコ内に4−(ペルフルオロノネニルオキシ)
ベンゾイルクロリド117.5g(0.20モル)および無水ジエ
チルエーテル300mlを入れて充分に撹拌混合した後、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250mlから成る混合溶液を30
分間かけて徐々に滴下した。
Example 1 4 equipped with cooling tube, dropping funnel, thermometer and stirrer
4- (perfluorononenyloxy) in a two-necked flask
After 117.5 g (0.20 mol) of benzoyl chloride and 300 ml of anhydrous diethyl ether were added and thoroughly mixed with stirring, the flask was cooled using an ice-water bath, and n-octylamine was added under the condition that the temperature of the reaction system did not rise sharply. 25.55g
(0.20 mol), triethylamine 22.27 g (0.22 mol) and anhydrous diethyl ether 250 ml
It was gradually added dropwise over a period of minutes.

滴下終了後、約0〜20℃において撹拌をさらに12時間
続行した。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
ムを溶離剤とするシ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ッ素アミド化合物1を111.
64g得た(収率:82%)。
After the completion of the dropping, stirring was continued at about 0 to 20 ° C for another 12 hours. A white precipitate (triethylamine hydrochloride) was filtered from the reaction mixture by suction filtration, the filtrate was washed with tap water and dilute hydrochloric acid, dried over anhydrous magnesium sulfate, and then concentrated. The fluorine-containing amide compound 1 was treated with silica gel column chromatography using 111.
64 g was obtained (yield: 82%).

得られた生成物の物性を以下の表−1に示す。 The physical properties of the obtained product are shown in Table 1 below.

実施例2〜6 実施例1の手順に準拠して含フッ素アミド化合物2〜
6を調製した。
Examples 2 to 6 Fluorine-containing amide compound 2 according to the procedure of Example 1
6 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.

発明の効果 本発明による含フッ素アミド化合物は、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。
EFFECTS OF THE INVENTION The fluorinated amide compound according to the present invention has excellent slidability, water / oil repellency, heat resistance and chemical resistance because it has a fluorinated group, and since it has an amide bond, it is polar. It is easy to use because it is highly stable and stable and has a high solubility in conventional organic solvents such as acetone.

従って、本発明による含フッ素アミド化合物は、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、金属表面処理剤、撥水撥
油剤等としても汎用し得る。
Therefore, the fluorinated amide compound according to the present invention is not only useful as a polymer surface modifier including imparting slidability to a polymer surface in contact with a metal, but also as a metal surface treatment agent, a water / oil repellent agent, etc. Can be general purpose.

───────────────────────────────────────────────────── フロントページの続き (72)発明者 立入 信彦 滋賀県甲賀郡甲西町大池町1―1 株式 会社ネオス内 (56)参考文献 特開 昭51−11084(JP,A) 特開 昭59−25358(JP,A) 特開 昭59−25359(JP,A) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Nobuhiko Tachiiri 1-1 Oike-cho, Konishi-cho, Koga-gun, Shiga Prefecture Neos Co., Ltd. (56) Reference JP-A-51-11084 (JP, A) JP-A-59- 25358 (JP, A) JP 59-25359 (JP, A)

Claims (1)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】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8〜30のアルキル基
を示し(但し、R1およびR2は同時には水素原子を示さな
い)、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。
1. A general formula [I]: (In the formula, R 1 and R 2 each independently represent a hydrogen atom or an alkyl group having 8 to 30 carbon atoms which may have a branched chain (provided that R 1 and R 2 represent hydrogen atoms at the same time). ), And n is a number of 1 or 2.).
JP63157449A 1988-06-25 1988-06-25 Fluorine-containing amide compound Expired - Fee Related JP2540602B2 (en)

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 JPH026448A (en) 1990-01-10
JP2540602B2 true 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)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5838475B2 (en) * 1974-07-17 1983-08-23 株式会社ネオス Fluorine-containing surfactant
JPS6050779B2 (en) * 1983-03-11 1985-11-11 株式会社ネオス Production method of ethylene oxide-added fluorine-containing compound
JPS6020373B2 (en) * 1983-03-11 1985-05-21 株式会社ネオス Method for producing fluorine-containing amino compounds

Also Published As

Publication number Publication date
JPH026448A (en) 1990-01-10

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