JPS59113005A - Preparation of poly-o-trifluoromethylstyrene - Google Patents
Preparation of poly-o-trifluoromethylstyreneInfo
- Publication number
- JPS59113005A JPS59113005A JP22285682A JP22285682A JPS59113005A JP S59113005 A JPS59113005 A JP S59113005A JP 22285682 A JP22285682 A JP 22285682A JP 22285682 A JP22285682 A JP 22285682A JP S59113005 A JPS59113005 A JP S59113005A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylstyrene
- poly
- polymerization initiator
- radical polymerization
- reaction
- 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
Abstract
Description
【発明の詳細な説明】
〔発明の属する技術分野〕
本発明は乳化重合によるポＩＪ −０−トリフルオロメ
チルスチレンの製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of the Invention] The present invention relates to a method for producing polyIJ-0-trifluoromethylstyrene by emulsion polymerization.
本発明は、０−１１Ｊフルオロメチルスチレンをラジカ
ル重合開始剤の存在下あるいは非存在下で、１００〜２
００℃の温度で塊状重合すると収率良くポリー〇−トリ
フルオロメチルスチレンが得られ、該重合体は優れた耐
熱性、電気絶縁性、成形加工性などの特徴を肩する優れ
た電気絶縁材料であること金見いだした。しかしながら
、該重合体を塊状重合法で製造する場合、反応に用いる
モノマーの量が多くなると、重合温度の制御が難しくな
り、また段られる該重合体の分子量は重合温度の経過に
より大きな影響を受けるため、再現性良く所望の分子量
の該重合体を得ることが難しくなるという欠点を有して
いる。また更に、塊状重合法で短時間に収率良く該重合
体を製造するには、反応を１００〜２００°Ｃの高い温
度条件の下に行なう必要があるという欠点を有している
。The present invention uses 0-11J fluoromethylstyrene in the presence or absence of a radical polymerization initiator.
Poly-trifluoromethylstyrene can be obtained in high yield by bulk polymerization at a temperature of 0.00°C, and this polymer is an excellent electrical insulating material with features such as excellent heat resistance, electrical insulation, and moldability. I found some money. However, when the polymer is produced by bulk polymerization, as the amount of monomers used in the reaction increases, it becomes difficult to control the polymerization temperature, and the molecular weight of the polymer is greatly affected by the progress of the polymerization temperature. Therefore, it has the disadvantage that it becomes difficult to obtain the polymer having a desired molecular weight with good reproducibility. Furthermore, in order to produce the polymer in high yield in a short period of time by bulk polymerization, it is necessary to carry out the reaction at a high temperature of 100 to 200°C.
本発明の目的は、０−）ＩＪフルオロメチルスチレンを
乳化重合させることにより、上記問題点を解消し、温和
で短時間の反応条件において高収率を与えるポリー〇−
トリフルオロメチルスチレンの製造方法を提供すること
にある。The purpose of the present invention is to solve the above-mentioned problems by emulsion polymerizing 0-)IJ fluoromethylstyrene, and to produce poly(0-)-
An object of the present invention is to provide a method for producing trifluoromethylstyrene.
本発明のポ！Ｊ−０−） ’Ｊフルオロメチルスチソン
の製造方法は、Ｏ−）！Ｊフルオロメチルスチレンをラ
ジカル重合開始剤の存在下に、水性乳化液中で重合させ
ることを゛特徴とするものＴある。Po of this invention! J-0-) 'The method for producing J-fluoromethylstithone is O-)! There is a product T characterized in that J fluoromethylstyrene is polymerized in an aqueous emulsion in the presence of a radical polymerization initiator.
以下において本発明の詳細な説明する。The present invention will be described in detail below.
本発明の乳化系では、０−）’Ｊフルオロメチルスチレ
ンと水の重量比は、通常、４０°６０〜５９５とするこ
とが好ましく、虹に好捷しくは３０ ： ７０〜１０：
９０である
乳化剤として使用する界面活性剤に特に制限はないが、
通常、アルキル硫酸塩、グリコールエーテル硫ｅ 塩、
アルキルベンゼンスルホン酸塩、アルキルスルホン酸塩
などのアニオン系界面活性剤あるいは第４級アンモニウ
ム塩、アルキルピリジニウム塩などのカチオン系界面活
性剤などが使用できる。乳化剤の使用量は、安定した乳
化液が得られる最少必要量以上であれば良いが、通常そ
の使用量は、Ｏ−トリフルオロメチルスチレンの重量に
対し、０１１〜５重量％であることが好捷しい。In the emulsion system of the present invention, the weight ratio of 0-)'J fluoromethylstyrene to water is usually preferably 40°60 to 595, preferably 30:70 to 10:
There are no particular restrictions on the surfactant used as an emulsifier, but
Usually, alkyl sulfate, glycol ether sulfate,
Anionic surfactants such as alkylbenzene sulfonates and alkyl sulfonates, and cationic surfactants such as quaternary ammonium salts and alkylpyridinium salts can be used. The amount of emulsifier used may be at least the minimum required amount to obtain a stable emulsion, but it is usually preferable that the amount used is 0.11 to 5% by weight based on the weight of O-trifluoromethylstyrene. It's sad.
本発明で使用するラジかル重合開始剤は水溶性ラジカル
重合開始剤である。例として過硫酸カリウム、過硫酸ア
ンモニウム、過酸化水素などが挙げられる。ラジカル重
合開始剤の使用量は、通常、０−トリフルオロメチルス
チレンの重量に対し、０１〜５重量係であることが好ま
しい。The radical polymerization initiator used in the present invention is a water-soluble radical polymerization initiator. Examples include potassium persulfate, ammonium persulfate, hydrogen peroxide, and the like. The amount of the radical polymerization initiator used is usually preferably 01 to 5 parts by weight relative to the weight of 0-trifluoromethylstyrene.
本発明の製造方法は上記した。−トルフルオロメチルス
チレン、水、乳化剤、ラジカル重合開始剤の所定量を混
合し、重合せしめればよい。反応条件は、激しい撹拌を
行ないつつ、 ３０’Ｃ以上の温度で、好ましくは５
０〜１００℃の温度において、４〜１０時間反応させる
ことにより遂行される。反応終了後、生成した該重合体
は常法に従って塩析などにより乳化液から分離される。The manufacturing method of the present invention has been described above. - Predetermined amounts of trifluoromethylstyrene, water, an emulsifier, and a radical polymerization initiator may be mixed and polymerized. The reaction conditions are a temperature of 30°C or higher, preferably 5°C, with vigorous stirring.
The reaction is carried out at a temperature of 0 to 100°C for 4 to 10 hours. After the reaction is completed, the produced polymer is separated from the emulsion by salting out or the like according to a conventional method.
本発明の製造方法によれば、０−１Ｊフルオロメチルス
チレンを乳化重合させることによシ、反応条件を容易に
制御することができ、しかも５０〜１００℃という温和
な反応条件で数時間で目的とするポ１，１−０−１リフ
ルオロメチルスチレンを高収率で得る仁とが可能である
。According to the production method of the present invention, the reaction conditions can be easily controlled by emulsion polymerizing 0-1J fluoromethylstyrene, and moreover, the desired amount can be obtained in a few hours under mild reaction conditions of 50 to 100°C. It is possible to obtain poly-1,1-0-1 trifluoromethylstyrene in high yield.
実施例１
内容量】１の反応容器に、窒素雰囲気下で、水２５０ｍ
１． Ｏ−トリフル′オロメチルスチレン５０ｇ１ラウ
リル硫酸ナトリウム０．５ｇ及び過硫酸カリウム１０ｇ
を入れ、激しく撹拌しつつ温度を６０〜６５°Ｃに保ち
、６時間反応を行なった。反応終了債、ラテックス状生
成物を１０％塩化ナトリウム水溶液２１中に注ぎ、白色
重合体を沈殿させた。該沈殿’ｃＰ別した徒、水および
メタノールで洗浄し、ポリー〇−トリフルオロメチルス
チレン４８ｇ（収率９６％）を得た。Example 1 Contents] 250 ml of water was added to the reaction vessel No. 1 under a nitrogen atmosphere.
1. 50 g O-trifluoromethylstyrene 1 0.5 g sodium lauryl sulfate and 10 g potassium persulfate
was added, and the temperature was maintained at 60 to 65°C while stirring vigorously, and the reaction was carried out for 6 hours. When the reaction was complete, the latex-like product was poured into 10% aqueous sodium chloride solution to precipitate a white polymer. The precipitate was separated and washed with water and methanol to obtain 48 g of poly-trifluoromethylstyrene (yield: 96%).
得られた該重合体の分子量をＧＰＣにより分析した結果
数平均分子量１７８，５００、重量平均分子量３０１゜
０００（ポリスチレン換算）であった。The molecular weight of the obtained polymer was analyzed by GPC, and the result was a number average molecular weight of 178,500 and a weight average molecular weight of 301.000 (in terms of polystyrene).
比較例
塊状重合法によシ実施例１と同じ反応温度で０〜トリフ
ルオロメチルスチレンの重合を行なった。Comparative Example Polymerization of 0 to trifluoromethylstyrene was carried out at the same reaction temperature as in Example 1 using the bulk polymerization method.
内容量２Ｑｍｌの重合管に、窒素雰囲気下で、０−トリ
フルオロメチルスチレン１０ｇとアゾビスイソブチロニ
トリル００３ｇを入れ、６０〜６５℃の温度で８時間反
行を行なった。反応終了後、内容物を５００ｍ１のメタ
ノール中に注ぎ、ポリー〇−トリフルオロメチルスチレ
ンを沈殿させた。該重合体の収量は１８ｇ、収率１８％
であった。得られた該重合体の分子量は、数平均分子量
６３．３００、重量平均分子量１４３５００（ポリスチ
レン換算）であった。In a polymerization tube having an internal capacity of 2 Qml, 10 g of 0-trifluoromethylstyrene and 003 g of azobisisobutyronitrile were placed in a nitrogen atmosphere, and reaction was carried out at a temperature of 60 to 65°C for 8 hours. After the reaction was completed, the contents were poured into 500 ml of methanol to precipitate poly-0-trifluoromethylstyrene. The yield of the polymer was 18 g, yield 18%.
Met. The molecular weight of the obtained polymer was a number average molecular weight of 63.300 and a weight average molecular weight of 143,500 (in terms of polystyrene).
実施例２
実施例１と同様にして、水４００ｍ１． Ｏ−） ＋）
フルオロメチルスチレン５０ ｇ＊ ドデシルベンゼン
スルホン酸ナトリウム０．３ｇ及び過硫酸カリウム１．
０ｇを入れ、９０〜９５℃の温度で５時間反応を行なっ
た。Example 2 In the same manner as in Example 1, 400 ml of water was prepared. O-) +)
Fluoromethylstyrene 50 g* Sodium dodecylbenzenesulfonate 0.3 g and potassium persulfate 1.
0g was added thereto, and the reaction was carried out at a temperature of 90 to 95°C for 5 hours.
生成物を実施例１と同様に処理し、ポＩ）−０−トリフ
ルオロメチルスチレン４７ｇ（収率９４％）を得た。The product was treated in the same manner as in Example 1 to obtain 47 g (yield: 94%) of poly(I)-0-trifluoromethylstyrene.
該重合体の分子１は、数平均分子量１４２４００．重量
平均分子量２４３，０００（ポリスチレン換算）であっ
た。Molecule 1 of the polymer has a number average molecular weight of 142,400. The weight average molecular weight was 243,000 (in terms of polystyrene).
実施例３
実施例１と同様にして、水２５０ｍ１． Ｏ−トリフル
オロメチルスチレン５０ ｇ’、 ラウリル硫酸ナト
リウム０５ｇ及び過硫酸カリウム０．８ｇを入れ、５０
〜５５℃で９時間反応を行なった。生成物を実施例１と
同様に処理し、ボＵ−０−トリフルオロメチルスチレン
４３ｇ（収率８６％）を得た。該重合体の分子量は、数
乎均分子量Ｊ５４，５００、重量平均分子量２５仏０（
１０（ポリスチレン換算）であった。Example 3 In the same manner as in Example 1, 250 ml of water was added. Add 50 g of O-trifluoromethylstyrene, 05 g of sodium lauryl sulfate, and 0.8 g of potassium persulfate, and
The reaction was carried out at ˜55° C. for 9 hours. The product was treated in the same manner as in Example 1 to obtain 43 g (yield: 86%) of U-0-trifluoromethylstyrene. The molecular weight of the polymer is J54,500, weight average molecular weight J50, and weight average molecular weight J54,500.
10 (in terms of polystyrene).
Claims (1)
の存在下で乳化重合させることを％徴とするポリ−０−
トリフルオロメチルスチレンの製造方法。Poly-0- which is characterized by emulsion polymerization of 0-trifluoromethylstyrene in the presence of a radical polymerization initiator
Method for producing trifluoromethylstyrene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22285682A JPS59113005A (en) | 1982-12-21 | 1982-12-21 | Preparation of poly-o-trifluoromethylstyrene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22285682A JPS59113005A (en) | 1982-12-21 | 1982-12-21 | Preparation of poly-o-trifluoromethylstyrene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS59113005A true JPS59113005A (en) | 1984-06-29 |
Family
ID=16788963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22285682A Pending JPS59113005A (en) | 1982-12-21 | 1982-12-21 | Preparation of poly-o-trifluoromethylstyrene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59113005A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0543055A (en) * | 1991-08-19 | 1993-02-23 | Toyoda Gosei Co Ltd | Workpiece conveyor device |
| EP2814853A4 (en) * | 2012-02-14 | 2015-09-30 | Akron Polymer Systems Inc | Method for the preparation of styrenic fluoropolymers |
-
1982
- 1982-12-21 JP JP22285682A patent/JPS59113005A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0543055A (en) * | 1991-08-19 | 1993-02-23 | Toyoda Gosei Co Ltd | Workpiece conveyor device |
| EP2814853A4 (en) * | 2012-02-14 | 2015-09-30 | Akron Polymer Systems Inc | Method for the preparation of styrenic fluoropolymers |
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