JPS621379B2 - - Google Patents
Info
- Publication number
- JPS621379B2 JPS621379B2 JP55044666A JP4466680A JPS621379B2 JP S621379 B2 JPS621379 B2 JP S621379B2 JP 55044666 A JP55044666 A JP 55044666A JP 4466680 A JP4466680 A JP 4466680A JP S621379 B2 JPS621379 B2 JP S621379B2
- Authority
- JP
- Japan
- Prior art keywords
- perfluoro
- pentene
- methylethyl
- methyl
- phthalic acid
- 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
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、次式
で表わされる４―〔ペルフルオロ―３―（１―メ
チルエチル）―４―メチル―２―ペンテン―２―
オキシ〕フタル酸及びその製法に関するものであ
る。式の化合物は文献未載の新規化合物であ
り、従来なかつたものである。[Detailed Description of the Invention] The present invention is based on the following formula 4-[perfluoro-3-(1-methylethyl)-4-methyl-2-pentene-2-
This article relates to oxy]phthalic acid and its production method. The compound of the formula is a novel compound that has not been described in any literature, and has never existed before.
式の化合物は文献未載の新規化合物であり、
例えばエポキシ樹脂用多フツ素化剤の製造のため
の出発物質として有用である。 The compound of the formula is a new compound that has not been described in any literature,
For example, it is useful as a starting material for the production of multifluorinating agents for epoxy resins.
式の化合物は、次式
で表わされるペルフルオロ―３―（１―メチルエ
チル）―４―メチル―２―ペンテン、ペルフルオ
ロ―３―エチル―２，４―ジメチル―２―ペンテ
ンを単独で、又は混合物として４―ヒドロキシフ
タル酸と縮合させることによつて製造することが
できる。本反応は式で表わされるヘキサフルオ
ロブロペンの三量体の一方又は混合物と４―ヒド
ロキシフタル酸のジメチルホルムアミド、ジメチ
ルアセトアミドなどの非プロトン性極性溶媒溶液
に、30℃以下、例えば室温でトリエチルアミンな
どの第３アミンを滴下しながら30〜60分間かきま
ぜることによつて行なうことができる。この反応
で、第３アミンの使用量は式の化合物に対して
１〜３モル倍量が適当であり過剰に用いた場合
は、反応終了後反応液を希塩酸水溶液で中和する
必要がある。The compound of the formula is Perfluoro-3-(1-methylethyl)-4-methyl-2-pentene and perfluoro-3-ethyl-2,4-dimethyl-2-pentene represented by 4-hydroxyphthalic acid alone or as a mixture. It can be produced by condensation. This reaction is carried out by adding one or a mixture of hexafluorobropene trimers represented by the formula and 4-hydroxyphthalic acid to a solution of an aprotic polar solvent such as dimethylformamide or dimethylacetamide at 30°C or below, for example, triethylamine, etc. at room temperature. This can be done by stirring for 30 to 60 minutes while dropping a tertiary amine. In this reaction, the appropriate amount of the tertiary amine to be used is 1 to 3 moles per mole of the compound of the formula; if it is used in excess, it is necessary to neutralize the reaction solution with a dilute aqueous hydrochloric acid solution after the reaction is completed.
実施例 １
ペルフルオロ―３―（１―メチルエチル）―４
―メチル―２―ペンテンンとペルフルオロ―３―
エチル―２，４―ジメチル―２―ペンテンの４対
６の混合物9.0ｇ（0.02モル）、４―ヒドロキシフ
タル酸3.64ｇ（0.02モル）をジメチルホルムアミ
ド25ml中に加え、トリエチルアミン6.06ｇ（0.06
モル）を５分間で滴下する。さらに室温で25分間
かきまぜる。反応終了後、反応混合物を1N―
HCl100mlにあけ、かきまぜる。析出する油にエ
チルエーテルを加え溶かす。エチルエーテル溶液
を洗浄液が中性になるまで水洗し、無水硫酸マグ
ネシウムで乾燥する。エチルエーテルを留去する
と融点147℃〜150℃の粗４―〔ペルフルオロ―３
―（１―メチルエチル）―４―メチル―２―ペン
テン―２―オキシ〕―フタル酸10.22ｇ（収率83
％）が得られる。エチルエーテル―ｎ―ヘキサン
系で再沈すると融点152℃〜153℃の純粋な４―
〔ペルフルオロ―３―（１―メチルエチル）―４
―メチル―２―ペンテン―２―オキシ〕―フタル
酸が得られる。Example 1 Perfluoro-3-(1-methylethyl)-4
-Methyl-2-pentene and perfluoro-3-
9.0 g (0.02 mol) of a 4:6 mixture of ethyl-2,4-dimethyl-2-pentene, 3.64 g (0.02 mol) of 4-hydroxyphthalic acid were added to 25 ml of dimethylformamide, and 6.06 g (0.06 mol) of triethylamine were added.
mol) dropwise over 5 minutes. Stir for another 25 minutes at room temperature. After the reaction is complete, the reaction mixture is diluted with 1N
Pour into 100ml of HCl and stir. Add ethyl ether to the precipitated oil and dissolve. The ethyl ether solution is washed with water until the washing solution becomes neutral, and dried over anhydrous magnesium sulfate. When ethyl ether is distilled off, crude 4-[perfluoro-3] with a melting point of 147°C to 150°C is produced.
-(1-methylethyl)-4-methyl-2-pentene-2-oxy]-phthalic acid 10.22 g (yield 83
%) is obtained. When reprecipitated with ethyl ether-n-hexane system, pure 4-
[Perfluoro-3-(1-methylethyl)-4
-Methyl-2-pentene-2-oxy]-phthalic acid is obtained.
元素分析値
Ｃ Ｈ Ｆ
計算値（％） 33.33 0.82 52.78
実測値（％） 33.06 0.89 52.92
このものは赤外線吸収スペクトルの1700cm-1、
1730cm-1（CO結合）、ならびにフツ素19核磁気共
嗚スペクトルで（CD3）2CO中、CFCl3を内部標準
としてδ−55.3（ｄ）、−70.3（Ｓ）、−71.8（ｄ）、
−165.8（qd）、−168.0（Sept、ｄ）により目的物
であることを確認した。Elemental analysis value C H F Calculated value (%) 33.33 0.82 52.78 Actual value (%) 33.06 0.89 52.92 This item has an infrared absorption spectrum of 1700 cm -1 ,
1730 cm -1 (CO bond) and Fluorine 19 nuclear magnetic resonance spectrum (CD 3 ) 2 in CO with CFCl 3 as internal standard δ -55.3 (d), -70.3 (S), -71.8 (d) ,
-165.8 (qd), -168.0 (Sept, d) confirmed that it was the target object.
実施例 ２
ペルフルオロ―３―（１―メチルエチル）―４
―メチル―２―ペンテン18.0ｇ（0.04モル）、４
―ヒドロキシフタル酸7.28ｇ（0.04モル）をジメ
チルアセトアミド50ml中に加え、トリエチルアミ
ンを8.08ｇ（0.08モル）を10分間で滴下する。さ
らに室温で20分間かきまぜる。以下実施例１と同
様に仕上げ処理すると実施例１と同じ生成物
18.18ｇ（収率74％）が得られる。融点152℃〜
153℃。Example 2 Perfluoro-3-(1-methylethyl)-4
-Methyl-2-pentene 18.0g (0.04mol), 4
- Add 7.28 g (0.04 mol) of hydroxyphthalic acid to 50 ml of dimethylacetamide, and add 8.08 g (0.08 mol) of triethylamine dropwise over 10 minutes. Stir for another 20 minutes at room temperature. Following finishing treatment as in Example 1, the same product as in Example 1 was obtained.
18.18 g (74% yield) is obtained. Melting point 152℃~
153℃.
本発明の化合物は、フタル酸であることと、
C9F17O基という多くのフツ素を有する置換基を
有するという二つの特徴を有している。 The compound of the present invention is phthalic acid;
It has two characteristics: it has many fluorine-containing substituents called C 9 F 17 O groups.
したがつて
(i) フタル酸であるため種々のポリマー、可塑剤
の合成原料として有用である。フタル酸から得
られるポリマーとしては、ジアリルフタレート
樹脂、アルキツド樹脂がある。 Therefore, (i) since it is a phthalic acid, it is useful as a raw material for the synthesis of various polymers and plasticizers. Polymers obtained from phthalic acid include diallyl phthalate resins and alkyd resins.
また無水フタル酸の形としてはエポキシ樹脂
の硬化剤として用いることができる。さらに、
フタル酸のアルキルエステルは塩化ビニル樹脂
の可塑剤として広く用いることができる。 In addition, in the form of phthalic anhydride, it can be used as a curing agent for epoxy resins. moreover,
Alkyl esters of phthalic acid can be widely used as plasticizers for vinyl chloride resins.
(ii) フツ素を多く含んでいるため、耐熱性、耐湿
性、耐候性に優れたポリマーを得ることができ
る。(ii) Since it contains a large amount of fluorine, it is possible to obtain a polymer with excellent heat resistance, moisture resistance, and weather resistance.
すなわち本発明の化合物は、種々のポリマー
の原料となり得るフタル酸構造と、特異な性能
の発現が期待できる多ホツ素置換基を有してい
るものであり、本化合物を用いてこれまでにな
い性能を有するポリマーを製造することが可能
である。 In other words, the compound of the present invention has a phthalic acid structure that can be used as a raw material for various polymers, and a polyboronous substituent that can be expected to exhibit unique performance. It is possible to produce polymers with performance.
Claims (1)
チルエチル）―４―メチル―２―ペンテン―２―
オキシ〕―フタル酸。 ２ 次式 で表わされるペルフルオロ―３―（１―メチルエ
チル）―４―メチル―２―ペンテン、ペルフルオ
ロ―３―エチル―２，４―ジメチル―２―ペンテ
ンを単独で又は混合物として４―ヒドロキシフタ
ル酸と縮合させることを特徴とする次式 で表わされる４―〔ペルフルオロ―３―（１―メ
チルエチル）―４―メチル―２―ペンテン―２―
オキシ〕―フタル酸の製法。[Claims] Linear formula 4-[perfluoro-3-(1-methylethyl)-4-methyl-2-pentene-2-
Oxy]-phthalic acid. Quadratic equation Condensation of perfluoro-3-(1-methylethyl)-4-methyl-2-pentene and perfluoro-3-ethyl-2,4-dimethyl-2-pentene, either alone or as a mixture, with 4-hydroxyphthalic acid. The following equation is characterized by 4-[perfluoro-3-(1-methylethyl)-4-methyl-2-pentene-2-
Production method of oxy]-phthalic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4466680A JPS56140951A (en) | 1980-04-07 | 1980-04-07 | 4- perfluoro-3- 1-methylethyl -4-methyl-2-penten-2-oxy - phthalic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4466680A JPS56140951A (en) | 1980-04-07 | 1980-04-07 | 4- perfluoro-3- 1-methylethyl -4-methyl-2-penten-2-oxy - phthalic acid and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56140951A JPS56140951A (en) | 1981-11-04 |
| JPS621379B2 true JPS621379B2 (en) | 1987-01-13 |
Family
ID=12697765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4466680A Granted JPS56140951A (en) | 1980-04-07 | 1980-04-07 | 4- perfluoro-3- 1-methylethyl -4-methyl-2-penten-2-oxy - phthalic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56140951A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69315030D1 (en) * | 1992-08-07 | 1997-12-11 | Fujikura Kasei Kk | Electrosensitive composition |
| JP2006335677A (en) * | 2005-06-01 | 2006-12-14 | Nippon Shokubai Co Ltd | Perfluoroalkenyl derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5756454B2 (en) * | 1974-03-07 | 1982-11-30 | ||
| JPS5912098B2 (en) * | 1974-03-08 | 1984-03-21 | 株式会社ネオス | Method for producing para-perfluoroalkenyloxybenzoic acid and its alkali metal salt |
| JPS52105141A (en) * | 1976-03-01 | 1977-09-03 | Central Glass Co Ltd | Preparation of perfluorononenyloxybenzoic acid |
-
1980
- 1980-04-07 JP JP4466680A patent/JPS56140951A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56140951A (en) | 1981-11-04 |
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