JP2592686B2 - Dibenzylsulfonium compound - Google Patents
Dibenzylsulfonium compoundInfo
- Publication number
- JP2592686B2 JP2592686B2 JP28567189A JP28567189A JP2592686B2 JP 2592686 B2 JP2592686 B2 JP 2592686B2 JP 28567189 A JP28567189 A JP 28567189A JP 28567189 A JP28567189 A JP 28567189A JP 2592686 B2 JP2592686 B2 JP 2592686B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- dibenzylsulfonium
- dibenzyl
- hydroxyphenylsulfonium
- present
- 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 - Lifetime
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規なジベンジルスルホニウム化合物に関す
る。さらに詳しくは、光および熱硬化組成物の硬化開始
剤として有用であり、特にエポキシ樹脂やスチレンなど
のカチオン重合性ビニル化合物の重合硬化開始剤として
の効果を有する新規ジベンジルスルホニウム化合物に関
する。Description: TECHNICAL FIELD The present invention relates to a novel dibenzylsulfonium compound. More specifically, the present invention relates to a novel dibenzylsulfonium compound which is useful as a curing initiator for a light and heat curable composition, and particularly has an effect as a polymerization curing initiator for cationically polymerizable vinyl compounds such as epoxy resins and styrene.
従来、カチオン重合性化合物の重合硬化開始剤とし
て、特開昭54-53181号にはｐ−ヒドロキシフェニルジメ
チルスルホニウム、ヘキサフルオロアルセネート類が公
知である。また、特開昭50-29511号にはｐ−ヒドロキシ
フェニルベンジルスルホニウム化合物について開示され
ており、米国特許第4034046号にはｐ−ヒドロキシフェ
ニルベンジルスルホニウムハロゲン化物について開示さ
れている。しかしながら、ジベンジル−４−ヒドロキシ
フェニルスルホニウムのポリフルオロ（亜）金属塩は公
知ではない。Hitherto, p-hydroxyphenyldimethylsulfonium and hexafluoroarsenates have been known as polymerization initiators for cationically polymerizable compounds in JP-A-54-53181. JP-A-50-29511 discloses a p-hydroxyphenylbenzylsulfonium compound, and U.S. Pat. No. 4,403,046 discloses a p-hydroxyphenylbenzylsulfonium halide. However, polyfluoro (sub) metal salts of dibenzyl-4-hydroxyphenylsulfonium are not known.
本発明は、下記一般式（Ｉ）で表わされる新規ジベン
ジルスルホニウム化合物に関するものであり、本化合物
は前記のとおり、ジベンジル−４−ヒドロキシフェニル
スルホニウムの（亜）金属ポリフロリドを要件としてい
る。The present invention relates to a novel dibenzylsulfonium compound represented by the following general formula (I), and as described above, this compound requires a (sub) metal polyfluoride of dibenzyl-4-hydroxyphenylsulfonium.
（ただしR1,R2は独立して水素，C1〜C4のアルキル基の
いずれかを示し、Ｘは、SbF6,PF6,AsF6を示す。） 本化合物の合成法を例示する。本化合物は、相当する
ジベンジルスルホニウムクロリド、あるいはジベンジル
スルホニウム メチルサルフェートを出発原料として、
所定の酸のアルカリ金属塩またはアンモニウム塩、例え
ばNaSbF6,KSbF6,NaPF6,KPF6,NaAsF6,KAsF6,NH4SbF6のい
ずれかと、所定の無水または含水有機溶媒中で反応させ
て合成する。この場合の有機溶媒としては、メタノー
ル、アセトン、酢酸エチル、エタノール、アセトニトリ
ル、プロパノールである。これ以外の例えばベンゼン、
トルエン類では、無機塩を実質上溶解させないため、反
応しない。また、DMF、DMSO類では、その溶解性のた
め、反応そのものは進行するものの、高沸点のために当
該反応系からの除去が困難である。 (However, R 1 and R 2 each independently represent hydrogen or an alkyl group of C 1 to C 4 , and X represents SbF 6 , PF 6 , or AsF 6. ) . This compound is prepared from the corresponding dibenzylsulfonium chloride or dibenzylsulfonium methyl sulfate as a starting material.
Reaction with a predetermined acid alkali metal salt or ammonium salt, for example, NaSbF 6 , KSbF 6 , NaPF 6 , KPF 6 , NaAsF 6 , KAsF 6 , NH 4 SbF 6 in a predetermined anhydrous or water-containing organic solvent Combine. In this case, the organic solvent includes methanol, acetone, ethyl acetate, ethanol, acetonitrile, and propanol. Others such as benzene,
The toluenes do not react because the inorganic salts are not substantially dissolved. Further, in DMF and DMSOs, the reaction itself proceeds due to its solubility, but it is difficult to remove it from the reaction system due to its high boiling point.
本発明の新規化合物は、光および／または硬化組成物
の硬化開始剤として有用であり、特にエポキシ樹脂やス
チレンなどのカチオン重合性ビニル化合物の重合硬化開
始剤としての効果を有している。即ち、本来不安定なス
ルホニウム化合物のアニオン部を、SbF6,PF6,AsF6に置
き換えることで、結晶性を上げ、これによって良好な安
定性が得られる。The novel compound of the present invention is useful as a curing initiator for light and / or a curable composition, and particularly has an effect as a polymerization curing initiator for cationically polymerizable vinyl compounds such as epoxy resins and styrene. That is, by substituting the anion portion of the originally unstable sulfonium compound with SbF 6 , PF 6 , or AsF 6 , the crystallinity is increased, and thereby good stability is obtained.
以下、実施例にて本発明を詳細にするが、本発明は下
記のみに限定されるものではない。Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to only the following.
実施例１ ジベンジル−４−ヒドロキシフェニルスルホニウム ヘ
キサフルオロアンチモネートの合成 ジベンジル−４−ヒドロキシフェニルスルホニウム
クロライド1.00g（0.003モル）をメタノール50mlに溶解
させ、撹拌しながら、KSbF6 0.80g（0.003モル）の粉末
を加え、更に１時間撹拌する。反応液を減圧濃縮し、残
渣を酢酸エチルで抽出する。酢酸エチル層を水洗、乾燥
後、濃縮する。残渣から白色結晶のジベンジル−４−ヒ
ドロキシフェニルスルホニウム ヘキサフルオロアンチ
モネート1.20g（収率75.9％）を得る。Example 1 Synthesis of dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate Dibenzyl-4-hydroxyphenylsulfonium
Chloride 1.00g of (0.003 mol) was dissolved in methanol 50 ml, with stirring, it was added a powder of KSbF 6 0.80g (0.003 mol), stirred for a further 1 hour. The reaction solution is concentrated under reduced pressure, and the residue is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried and concentrated. From the residue, 1.20 g (yield: 75.9%) of white crystals of dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate are obtained.
融点91.0〜94.0℃ IR （KBr） 3100cm-1,660cm-1 NMR （Acetone−d6）ppm δ＝4.94〜5.41（4H,dd,PhCH2-×２） δ＝6.94〜7.76（14H,m,-C6H4-,C6H5-×２） δ＝9.70（1H, s, HO−） 元素分析C20H19OSSbF6 理論値C;44.22％,H;3.52％ 測定値C;43.99％,H;3.47％ 実施例２ ジベンジル−４−ヒドロキシフェニルスルホニウム
ヘキサフルオロアンチモネートの合成 ジベンジル−４−ヒドロキシフェニルスルホニウム
メチルサルフェート 1.26g（0.003モル）をメタノール
80mlに溶解させ、実施例１と同様な方法で合成し、ジベ
ンジル−４−ヒドロキシフェニルスルホニウム ヘキサ
フルオロアンチモネート1.33g（収率91.1％）を得る。Mp 91.0~94.0 ℃ IR (KBr) 3100cm -1 , 660cm -1 NMR (Acetone-d 6) ppm δ = 4.94~5.41 (4H, dd, PhCH 2- × 2) δ = 6.94~7.76 (14H, m, -C 6 H 4-, C 6 H 5- × 2) δ = 9.70 (1H, s, HO-) elemental analysis C 20 H 19 OSSbF 6 theory C; 44.22%, H; 3.52 % measured value C; 43.99 %, H; 3.47% Example 2 Dibenzyl-4-hydroxyphenylsulfonium
Synthesis of hexafluoroantimonate dibenzyl-4-hydroxyphenylsulfonium
1.26 g (0.003 mol) of methyl sulfate in methanol
It is dissolved in 80 ml and synthesized in the same manner as in Example 1 to obtain 1.33 g (yield 91.1%) of dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate.
（発明の効果） 本発明の新規ジベンジルスルホニウム化合物は、高純
度を必要とするエポキシ硬化開始剤、更に工業用中間原
料として有利である。よって所期の目的を達成する。(Effect of the Invention) The novel dibenzylsulfonium compound of the present invention is advantageous as an epoxy curing initiator requiring high purity, and as an industrial intermediate material. Therefore, the intended purpose is achieved.
Claims (1)
ホニウム化合物。 （ただしR1,R2は独立して水素，C1〜C4のアルキル基の
いずれかを示し、Ｘは、SbF6,PF6,AsF6を示す。）1. A dibenzylsulfonium compound represented by the general formula (I). (However, R 1 and R 2 independently represent hydrogen or an alkyl group of C 1 to C 4 , and X represents SbF 6 , PF 6 or AsF 6. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28567189A JP2592686B2 (en) | 1989-10-31 | 1989-10-31 | Dibenzylsulfonium compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP28567189A JP2592686B2 (en) | 1989-10-31 | 1989-10-31 | Dibenzylsulfonium compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03145459A JPH03145459A (en) | 1991-06-20 |
| JP2592686B2 true JP2592686B2 (en) | 1997-03-19 |
Family
ID=17694547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP28567189A Expired - Lifetime JP2592686B2 (en) | 1989-10-31 | 1989-10-31 | Dibenzylsulfonium compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2592686B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2943008B2 (en) | 1989-10-18 | 1999-08-30 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Thermosetting mixture |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4122085B2 (en) * | 1998-03-11 | 2008-07-23 | 三新化学工業株式会社 | Method for producing sulfonium compound |
| JP4566642B2 (en) * | 2004-07-21 | 2010-10-20 | 三新化学工業株式会社 | Method for producing sulfonium compound |
| EP2000297A1 (en) | 2006-03-24 | 2008-12-10 | Konica Minolta Medical & Graphic, Inc. | Transparent barrier sheet and method for producing transparent barrier sheet |
| JPWO2007111098A1 (en) | 2006-03-24 | 2009-08-06 | コニカミノルタエムジー株式会社 | Transparent barrier sheet and method for producing the same |
| EP2000296A2 (en) | 2006-03-24 | 2008-12-10 | Konica Minolta Medical & Graphic, Inc. | Transparent barrier sheet and production method of transparent barrier sheet |
| EP2000299A4 (en) | 2006-03-24 | 2009-08-05 | Konica Minolta Med & Graphic | Transparent barrier sheet and method for producing transparent barrier sheet |
-
1989
- 1989-10-31 JP JP28567189A patent/JP2592686B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2943008B2 (en) | 1989-10-18 | 1999-08-30 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Thermosetting mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03145459A (en) | 1991-06-20 |
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