JPH05213929A - Fluorine-containing compound and its production - Google Patents
Fluorine-containing compound and its productionInfo
- Publication number
- JPH05213929A JPH05213929A JP4244692A JP4244692A JPH05213929A JP H05213929 A JPH05213929 A JP H05213929A JP 4244692 A JP4244692 A JP 4244692A JP 4244692 A JP4244692 A JP 4244692A JP H05213929 A JPH05213929 A JP H05213929A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- fluorine
- reaction
- containing compound
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、新規な含フッ素化合物
及びその製造方法に関するものである。FIELD OF THE INVENTION The present invention relates to a novel fluorine-containing compound and a method for producing the same.
【０００２】[0002]
【従来の技術】本発明の一般式（１）（式中、Ｒ1 は炭
素数２〜７のポリフルオロアルキル基）は文献未載の新
規化合物である。2. Description of the Related Art The general formula (1) of the present invention (wherein R 1 is a polyfluoroalkyl group having 2 to 7 carbon atoms) is a novel compound which has not been published in the literature.
【０００３】[0003]
【化４】 [Chemical 4]
【０００４】このような例は、USP 3,307,330 に一般式
（３）で示される化合物が知られている。この化合物
は、単独重合または他のモノマーと共重合して含フッ素
重合体を与える。しかし、トリフルオロメチル基以外の
ポリフルオロアルキル基が５員環上に置換しているよう
な例は知られていない。そして我々は、５員環上に置換
基をトリフルオロメチル基よりかさ高い置換基に変更す
ることによって、重合体の密度が減少し、屈折率が低下
することを新たに見いだした。As such an example, a compound represented by the general formula (3) is known in USP 3,307,330. This compound is homopolymerized or copolymerized with another monomer to give a fluoropolymer. However, there is no known example in which a polyfluoroalkyl group other than the trifluoromethyl group is substituted on the 5-membered ring. Then, we newly found that by changing the substituent on the 5-membered ring to a bulkier substituent than the trifluoromethyl group, the density of the polymer was decreased and the refractive index was decreased.
【０００５】[0005]
【化５】 [Chemical 5]
【０００６】一方、USP 3,978,030 に一般式（４）で示
される化合物が知られており、重合により低屈折率のフ
ッ素樹脂が得られるが、Ｒ2 、Ｒ3 の置換基がかさ高く
なるにつれてモノマーの熱的安定性が低下することが、
知られている。（J.Am.Chem.Soc.,112,9671(1990) ）On the other hand, a compound represented by the general formula (4) is known in USP 3,978,030, and a fluororesin having a low refractive index can be obtained by polymerization, but as the substituents of R 2 and R 3 become bulky, the monomer becomes The thermal stability of
Are known. (J.Am.Chem.Soc., 112,9671 (1990))
【０００７】[0007]
【化６】 [Chemical 6]
【０００８】[0008]
【発明が解決しようとする課題】本発明は、従来知られ
ていなかった一般式（１）（式中、Ｒ1 は炭素数２〜７
のポリフルオロアルキル基）で表される熱的に安定で重
合により従来になく低屈折率の重合体をあたえるような
新規な含フッ素化合物を提供することを目的とするもの
である。DISCLOSURE OF THE INVENTION The present invention is based on the previously unknown general formula (1) (in the formula, R 1 has 2 to 7 carbon atoms).
It is an object of the present invention to provide a novel fluorine-containing compound represented by the polyfluoroalkyl group (1), which is thermally stable and can be polymerized to give a polymer having a low refractive index than ever before.
【０００９】[0009]
【化７】 [Chemical 7]
【００１０】[0010]
【課題を解決するための手段】本発明は、第一に、一般
式（１）（式中、Ｒ1 は炭素数２〜７のポリフルオロア
ルキル基）で表される含フッ素化合物を提供するもので
あり、第二に、一般式（２）（式中、Ｒ1 は炭素数２〜
７のポリフルオロアルキル基、Ｘは、ＦまたはＯＭ、Ｍ
は、アルカリ金属）を熱分解させることを特徴とする一
般式（１）（式中、Ｒ1 は炭素数２〜７のポリフルオロ
アルキル基）で表される新規含フッ素化合物の製造方法
を提供するものである。The present invention first provides a fluorine-containing compound represented by the general formula (1) (wherein R 1 is a polyfluoroalkyl group having 2 to 7 carbon atoms). Secondly, the general formula (2) (in the formula, R 1 has 2 to 2 carbon atoms).
7 is a polyfluoroalkyl group, X is F or OM, M
Provides a method for producing a novel fluorine-containing compound represented by the general formula (1) (wherein R 1 is a polyfluoroalkyl group having 2 to 7 carbon atoms), characterized by thermally decomposing an alkali metal). To do.
【００１１】[0011]
【化８】 [Chemical 8]
【００１２】[0012]
【化９】 [Chemical 9]
【００１３】本発明の含フッ素化合物は、含フッ素ポリ
マーを合成する際のコモノマーとして、また単独重合の
ためのモノマーとして有効であり、例えば次のように合
成することが可能である。The fluorine-containing compound of the present invention is effective as a comonomer when synthesizing a fluorine-containing polymer and as a monomer for homopolymerization. For example, it can be synthesized as follows.
【００１４】[0014]
【化１０】 [Chemical 10]
【００１５】即ち、含フッ素末端オレフィン化合物
（Ａ）を酸素による直接酸化または、次亜塩素酸ナトリ
ウム水溶液と相間移動触媒存在下の酸化反応で（Ｂ）を
得ることができる。さらに（Ｂ）をカルボニル化合物存
在下で反応させるとα−ケトカルボン酸フルオリド
（Ｃ）に変換することができる。（Ｃ）を金属フッ化物
存在下、ヘキサフルオロプロペンオキシドと反応させて
（Ｄ）を得、熱分解により本発明の新規含フッ素化合物
（Ｅ）を得ることができる。That is, the fluorine-containing terminal olefin compound (A) can be directly oxidized with oxygen or can be obtained by the oxidation reaction in the presence of a phase transfer catalyst with an aqueous solution of sodium hypochlorite. Further, by reacting (B) in the presence of a carbonyl compound, it can be converted to an α-ketocarboxylic acid fluoride (C). By reacting (C) with hexafluoropropene oxide in the presence of a metal fluoride to obtain (D), the novel fluorine-containing compound (E) of the present invention can be obtained by thermal decomposition.
【００１６】（Ａ）の酸素による直接酸化は、速やかに
進行し、（Ｂ）を定量的に与える。反応は、トリクロロ
トリフルオロエタン等の不活性溶媒を使用しても良い
が、無溶媒でも問題なく反応する。反応温度は、５０℃
〜２００℃、好ましくは、８０℃〜１５０℃であり、反
応温度が低い場合には、転化率が低くなり、反応温度が
高い場合には、分解生成物が多くなる。また、次亜塩素
酸ナトリウム水溶液を用いた（Ａ）の酸化反応では、テ
トラオクチルアンモニウムクロリド等の相間移動触媒存
在下、トリクロロトリフルオロエタン等の不活性溶媒ま
たは無溶媒中、反応させることにより（Ｂ）を得ること
ができる。このときの反応温度は、０℃〜５０℃であ
る。The direct oxidation of (A) with oxygen proceeds rapidly to give (B) quantitatively. For the reaction, an inert solvent such as trichlorotrifluoroethane may be used, but the reaction can be carried out without any problem without using a solvent. Reaction temperature is 50 ℃
˜200 ° C., preferably 80 ° C. to 150 ° C. When the reaction temperature is low, the conversion rate is low, and when the reaction temperature is high, the decomposition products are large. In addition, in the oxidation reaction of (A) using an aqueous solution of sodium hypochlorite, by reacting in the presence of a phase transfer catalyst such as tetraoctyl ammonium chloride in an inert solvent such as trichlorotrifluoroethane or no solvent ( B) can be obtained. The reaction temperature at this time is 0 ° C to 50 ° C.
【００１７】Ｒ1 の構造は、炭素数２〜７であればとく
に限定するものではないが例えば、-CF2CF3,-CF(CF3)2,
-CF2CF2CF3,-CF2CF2CF2CF3,-CF2CF2CF2CF2CF3,-CF2CF(C
F3)2-CF2CF2CF2H,-CF2CF2OCFHCF3等があげられる。The structure of R 1 is not particularly limited as long as it has 2 to 7 carbon atoms. For example, -CF 2 CF 3 , -CF (CF 3 ) 2 ,
-CF 2 CF 2 CF 3 ,, CF 2 CF 2 CF 2 CF 3 , -CF 2 CF 2 CF 2 CF 2 CF 3 , -CF 2 CF (C
F 3) 2 -CF 2 CF 2 CF 2 H, or the like -CF 2 CF 2 OCFHCF 3 and the like.
【００１８】（Ｂ）をたとえばベンゾフェノンやジメチ
ルホルムアミド等のカルボニル化合物と反応させること
により（Ｃ）を得ることができる。このときの反応温度
は、０℃〜２８０℃でありカルボニル化合物の種類によ
り最適温度が異なる。（Ｃ）は、反応条件下容易に
（Ｆ）なる構造に二量化することがある。しかし、
（Ｆ）は、（Ｃ）と同様の条件で次の反応に用いること
ができる。(C) can be obtained by reacting (B) with a carbonyl compound such as benzophenone or dimethylformamide. The reaction temperature at this time is 0 ° C. to 280 ° C., and the optimum temperature varies depending on the type of carbonyl compound. (C) may be easily dimerized into a structure (F) under reaction conditions. But,
(F) can be used in the next reaction under the same conditions as (C).
【００１９】[0019]
【化１１】 [Chemical 11]
【００２０】（Ｃ）または（Ｆ）とヘキサフルオロプロ
ペンオキシドとの反応は、触媒量のフッ化セシウム等の
アルカリ金属フッ化物存在下、ジエチレングリコールジ
メチルエーテル等の極性溶媒中、１００℃〜１８０℃で
反応させることにより（Ｄ）を得ることができる。反応
温度が低い場合には、異性体（Ｇ）が主に生成してしま
う。（Ｇ）は、触媒量のフッ化セシウム等のアルカリ金
属フッ化物存在下、ジエチレングリコールジメチルエー
テル等の極性溶媒中、１００℃〜１８０℃で異性化させ
て（Ｄ）を得ることができる。The reaction of (C) or (F) with hexafluoropropene oxide is carried out at 100 ° C to 180 ° C in a polar solvent such as diethylene glycol dimethyl ether in the presence of a catalytic amount of an alkali metal fluoride such as cesium fluoride. By doing so, (D) can be obtained. When the reaction temperature is low, the isomer (G) is mainly produced. (G) can be obtained by isomerizing (G) at 100 ° C. to 180 ° C. in a polar solvent such as diethylene glycol dimethyl ether in the presence of a catalytic amount of an alkali metal fluoride such as cesium fluoride.
【００２１】[0021]
【化１２】 [Chemical 12]
【００２２】（Ｅ）は、（Ｄ）の気相熱分解反応もしく
は、（Ｄ）と水酸化アルカリとを反応して得られるカル
ボン酸アルカリ塩の熱分解反応により得ることができ
る。（Ｄ）の気相熱分解反応における反応温度は、２５
０℃〜４００℃、好ましくは２８０℃〜３５０℃であ
り、またカルボン酸アルカリ塩の熱分解反応における反
応温度は、１５０℃〜３００℃、好ましくは２００℃〜
２８０℃である。反応温度が低い場合には、変換率が低
くなり、また高い場合には、分解生成物量が多くなる。(E) can be obtained by the gas phase thermal decomposition reaction of (D) or the thermal decomposition reaction of an alkali carboxylic acid salt obtained by reacting (D) with an alkali hydroxide. The reaction temperature in the gas phase pyrolysis reaction of (D) is 25
0 ° C to 400 ° C, preferably 280 ° C to 350 ° C, and the reaction temperature in the thermal decomposition reaction of the carboxylic acid alkali salt is 150 ° C to 300 ° C, preferably 200 ° C to
280 ° C. When the reaction temperature is low, the conversion rate is low, and when it is high, the amount of decomposition products is high.
【００２３】[0023]
【作用】本発明の含フッ素化合物は、単独重合により特
殊な溶媒に可溶な非晶質の含フッ素ポリマーを提供する
ことができる。また、他のコモノマーと共重合すること
により、特殊な溶媒に可溶な含フッ素ポリマーを提供す
ることができる。The fluorine-containing compound of the present invention can provide an amorphous fluorine-containing polymer soluble in a special solvent by homopolymerization. Further, by copolymerizing with another comonomer, a fluoropolymer soluble in a special solvent can be provided.
【００２４】[0024]
実施例１ パーフルオロ−２−メチル−２−フルオロカルボニル−
４−プロピル−１，３−ジオキソラン２０５ｇ（０．５
モル）と６６ｇの水酸化カリウム（１５％含水品）を溶
解した１０００ｍｌのエタノールをゆっくり混合する。
反応混合物の溶媒を留去し蒸発乾固させた後、減圧下２
２０℃で熱分解する。トラップに捕集された液を蒸留す
ることにより、目的生成物パーフルオロ−２−メチレン
−４−プロピル−１，３−ジオキソラン１４４．５ｇ
（８４％）を得た。Example 1 Perfluoro-2-methyl-2-fluorocarbonyl-
205 g of 4-propyl-1,3-dioxolane (0.5
Mol) and 66 g of potassium hydroxide (15% hydrous product) dissolved in 1000 ml of ethanol are slowly mixed.
After distilling off the solvent of the reaction mixture and evaporating to dryness, 2
Pyrolyzes at 20 ° C. By distilling the liquid collected in the trap, 144.5 g of the target product, perfluoro-2-methylene-4-propyl-1,3-dioxolane, was obtained.
(84%) was obtained.
【００２５】bp.84.0 ℃19 FーNMR(δppm,CFCl3 基準) -80.6(3F,CF3), -85.8(dd,
2F,CF2O), -122.6(2F,CFCF2), -124.4(2F,CF2CF3), -12
6.0(dd,2F,=CF2), -128.8(1F,CF)Bp.84.0 ° C. 19 F-NMR (δppm, CFCl 3 standard) -80.6 (3F, CF 3 ), -85.8 (dd,
2F, CF 2 O), -122.6 (2F, CFCF 2 ), -124.4 (2F, CF 2 CF 3 ), -12
6.0 (dd, 2F, = CF 2 ), -128.8 (1F, CF)
【００２６】また、この化合物は、１００℃に保って１
時間貯蔵したが、分解生成物は認められなかった。Further, this compound was kept at 100 ° C.
It was stored for a period of time, but no decomposition products were found.
【００２７】[0027]
【発明の効果】本発明の含フッ素化合物は、単独重合に
より特殊な溶媒に可溶な非晶質の含フッ素ポリマーを提
供することができる。また、他のコモノマーと共重合す
ることにより、特殊な溶媒に可溶な含フッ素ポリマーを
提供することができる。また、この溶液を用いて低反射
コートや薄膜等を作ることができる。INDUSTRIAL APPLICABILITY The fluorine-containing compound of the present invention can provide an amorphous fluorine-containing polymer soluble in a special solvent by homopolymerization. Further, by copolymerizing with another comonomer, a fluoropolymer soluble in a special solvent can be provided. In addition, a low reflection coat, a thin film, or the like can be formed using this solution.
Claims (2)
のポリフルオロアルキル基）で表される含フッ素化合
物。 【化１】 1. General formula (1) (wherein R 1 is a carbon number of 2 to 7)
Fluorine-containing compound represented by the polyfluoroalkyl group of. [Chemical 1]
のポリフルオロアルキル基、Ｘは、ＦまたはＯＭ、Ｍ
は、アルカリ金属）を熱分解させることを特徴とする一
般式（１）（式中、Ｒ1 は炭素数２〜７のポリフルオロ
アルキル基）で表される含フッ素化合物の製造方法。 【化２】 【化３】 2. General formula (2) (wherein R 1 has 2 to 7 carbon atoms).
X is F or OM, M
Is a thermal decomposition of an alkali metal), and a method for producing a fluorine-containing compound represented by the general formula (1) (wherein R 1 is a polyfluoroalkyl group having 2 to 7 carbon atoms). [Chemical 2] [Chemical 3]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4042446A JP3043172B2 (en) | 1992-01-31 | 1992-01-31 | Fluorine-containing compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4042446A JP3043172B2 (en) | 1992-01-31 | 1992-01-31 | Fluorine-containing compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05213929A true JPH05213929A (en) | 1993-08-24 |
| JP3043172B2 JP3043172B2 (en) | 2000-05-22 |
Family
ID=12636305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4042446A Expired - Fee Related JP3043172B2 (en) | 1992-01-31 | 1992-01-31 | Fluorine-containing compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3043172B2 (en) |
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-
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