JPH0737426B2 - New benzyl ammonium salt - Google Patents
New benzyl ammonium saltInfo
- Publication number
- JPH0737426B2 JPH0737426B2 JP1142541A JP14254189A JPH0737426B2 JP H0737426 B2 JPH0737426 B2 JP H0737426B2 JP 1142541 A JP1142541 A JP 1142541A JP 14254189 A JP14254189 A JP 14254189A JP H0737426 B2 JPH0737426 B2 JP H0737426B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- hexafluoroantimonate
- group
- chloride
- synthesis
- 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
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Description
【発明の詳細な説明】 本発明の背景 これまでカチオン重合し得るモノマーのカチオン重合反
応の開始剤としては、塩化アルミニウム等のフリーデル
クラフト触媒、三フッ化ホウ素ジエチルエーテル錯体、
光で開裂するオニウム塩(イオウ、セレン、テルル)ま
たはジアリルヨードニウム塩、熱的に開裂する芳香族ま
たは脂肪酸スルホニウム塩などが知られている。これら
のうち熱的に開裂してカルボニウムカチオンを生じ得る
開始剤(熱潜在性カチオン開始剤)は、例えば一液型エ
ポキシ樹脂の硬化剤として使用すると常温では反応せ
ず、120℃以上のような高温において重合反応を開始さ
せるので、ポットライフおよび貯蔵安定性を向上させる
硬化剤として注目されている。特開昭58−37003および
同58−37004参照。しかしながらスルホニウム塩型開始
剤は副生するイオン化合物が悪臭を発し、使用面で制約
を受ける。DETAILED DESCRIPTION OF THE INVENTION As an initiator of a cationic polymerization reaction of a monomer capable of undergoing cationic polymerization, Friedel-Crafts catalyst such as aluminum chloride, boron trifluoride diethyl ether complex,
Light-cleavable onium salts (sulfur, selenium, tellurium) or diallyliodonium salts, and thermally-cleavable aromatic or fatty acid sulfonium salts are known. Of these, initiators that can be thermally cleaved to generate carbonium cations (thermal latent cation initiators) do not react at room temperature when used as a curing agent for one-pack type epoxy resins, for example, at temperatures above 120 ° C. Since it initiates the polymerization reaction at extremely high temperatures, it has been attracting attention as a curing agent that improves pot life and storage stability. See JP-A-58-37003 and JP-A-58-37004. However, the sulfonium salt type initiator is restricted in its use because the ionic compound produced as a by-product gives off a bad odor.
本発明者らの特願平1−79468号は、悪臭を発生しない
熱潜在性カチオン開始剤としてベンジルアンモニウム塩
型化合物を開示している。またこの化合物は重合物(硬
化物)を着色しない利点がある。Japanese Patent Application No. 1-79468 of the present inventors discloses a benzylammonium salt type compound as a heat-latent cation initiator which does not generate a malodor. Further, this compound has an advantage that the polymer (cured product) is not colored.
本発明者はその後の研究により、このベンジルアンモニ
ウム塩型化合物のベンジル基のα位へ置換基を導入する
ことにより、開裂してベンジルカチオンを発生する温度
を低くすることに成功した。The present inventor succeeded in lowering the temperature at which cleavage occurs to generate a benzyl cation by introducing a substituent into the α-position of the benzyl group of this benzylammonium salt type compound in the subsequent research.
本発明の開示 本発明は、式I の新規ベンジルアンモニウム塩を提供する。DISCLOSURE OF THE INVENTION The present invention provides compounds of formula I The novel benzyl ammonium salt of
式中、R1,R2,R3は水素,塩素,メチル基またはニトロ基
から選ばれる基であり、 R4,R5は一方が水素で他方が塩素またはメチル基から選
ばれる基であるか、または両方が塩素またはメチル基か
ら選ばれる基であり、 R6,R7,R8はメチル基,エチル基,2−ヒドロキシエチル基
またはフェニル基から選ばれる基であり、 MはAs,Sb,BまたはPであり、 Xはハロゲンであり、 nはMがBである時は4であり、他の場合は6である。In the formula, R 1 , R 2 , and R 3 are groups selected from hydrogen, chlorine, a methyl group, or a nitro group, and R 4 and R 5 are one group selected from hydrogen and the other is selected from a chlorine or methyl group. Or both are groups selected from chlorine or a methyl group, R 6 , R 7 and R 8 are groups selected from a methyl group, an ethyl group, a 2-hydroxyethyl group or a phenyl group, and M is As, Sb, B or P, X is halogen, n is 4 when M is B, and 6 otherwise.
式Iにおいてアルキルおよびアルケニル(それから誘導
される基のアルキル部分を含む)の炭素数は好ましくは
4以下である。In formula I, the alkyl and alkenyl (including the alkyl part of the group derived therefrom) preferably has 4 or less carbon atoms.
式Iの化合物は、式II (式中、R6,R7,R8は前記に同じ。)の3級アミンを、式
III (式中、R1,R2,R3,R4,R5は前記に同じ。)のα−置換ベ
ンジルハライドで4級化し、生成する4級アンモニウム
のハライド陰イオンをMXn-陰イオンで交換することがで
きる。すなわち式Iのアンモニウム塩の対応するアンモ
ニウムハライドに、MXn-イオンのアルカリ金属塩を反応
させる。The compound of formula I has the formula II (In the formula, R 6 , R 7 and R 8 are the same as above.)
III (In the formula, R 1 , R 2 , R 3 , R 4 , and R 5 are the same as above.) Quaternized with an α-substituted benzyl halide, and the resulting quaternary ammonium halide anion is converted to MXn − anion. Can be exchanged. Thus, the corresponding ammonium halide of the ammonium salt of formula I is reacted with the alkali metal salt of MXn - ion.
式Iの化合物は、温度が上昇するとき開裂して対応する
カルボニウムカチオン、式 を生じ、オレフィン類、ビニルエーテル、スチレン誘導
体、ジエン類、カルボニル化合物、環状エーテル、エポ
キシド、環状エステル、環状アミドなどのカチオン重合
し得るモノマーの重合連鎖反応を開始させる。しかし常
温では殆ど不活性であるが、加熱して始めて開始剤とし
ての機能を発揮するので、例えば一液型エポキシ樹脂の
硬化剤などその熱潜在性を利用する用途に適している。The compound of formula I is cleaved when the temperature increases to give the corresponding carbonium cation, To initiate a polymerization chain reaction of cationically polymerizable monomers such as olefins, vinyl ethers, styrene derivatives, dienes, carbonyl compounds, cyclic ethers, epoxides, cyclic esters and cyclic amides. However, it is almost inactive at room temperature, but since it functions as an initiator only after heating, it is suitable for applications such as a curing agent for a one-pack type epoxy resin that utilizes its thermal potential.
実施例1 N−α−メチルベンジル−N,N−ジメチルアニリニウム
ヘキサフルオロアンチモネートの合成 α−メチルベンジルクロライド4.218g(0.03mol)及び
N,N−ジメチルアニリン3.638g(0.03mol)をメタノール
40mlに溶解し、40℃で3日間反応させた。Example 1 Synthesis of N-α-methylbenzyl-N, N-dimethylanilinium hexafluoroantimonate 4.218 g (0.03 mol) of α-methylbenzyl chloride and
N, N-dimethylaniline 3.638 g (0.03 mol) in methanol
It was dissolved in 40 ml and reacted at 40 ° C. for 3 days.
反応終了溶液をエバポレーターで揮散させ、水−エーテ
ルを加え未反応物をエーテル層へ抽出し塩化物を精製し
た。The reaction completed solution was volatilized with an evaporator, water-ether was added, and unreacted substances were extracted into an ether layer to purify chloride.
水層の塩化物にソジウムヘキサフルオロアンチモネート
7.77g(0.03mol)を加え、表記化合物を得た。Sodium hexafluoroantimonate in chloride of water layer
7.77 g (0.03 mol) was added to obtain the title compound.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),3.6ppm(s,6H,Me),4.8−4.9ppm
(q,1H,CH),7.1−7.6ppm(m,10H,Ph) 実施例2 N−2−ヒドロキシエチル−N−α−メチルベンジル−
N,N−ジメチルアンモニウムヘキサフルオロアンチモネ
ートの合成 α−メチルベンジルクロライド,N,N−ジメチルエタノー
ルアミン及びソジウムヘキサフルオロアンチモネートを
用いて実施例1と同様の方法により表記化合物を得た。1.7ppm (d, 3H, Me), 3.6ppm (s, 6H, Me), 4.8-4.9ppm
(Q, 1H, CH), 7.1-7.6ppm (m, 10H, Ph) Example 2 N-2-hydroxyethyl-N-α-methylbenzyl-
Synthesis of N, N-dimethylammonium hexafluoroantimonate The title compound was obtained in the same manner as in Example 1 using α-methylbenzyl chloride, N, N-dimethylethanolamine and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),2.9−3.0(t,6H,Me),3.1ppm(s,6
H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2H,CH2),
4.8ppm(q,1H,CH),7.5−7.6ppm(m,5H,Ph) 実施例3 N−α−メチルベンジル−N,N,N−トリメチルアンモニ
ウムヘキサフルオロアンチモネートの合成 α−メチルベンジルクロライド,トリメチルアミン及び
ソジウムヘキサフルオロアンチモネートを用いて実施例
1と同様の方法により表記化合物を得た。1.7ppm (d, 3H, Me), 2.9-3.0 (t, 6H, Me), 3.1ppm (s, 6
H, Me), 3.3-3.4ppm (q , 2H, CH 2), 3.9ppm (q, 2H, CH 2),
4.8 ppm (q, 1H, CH), 7.5-7.6 ppm (m, 5H, Ph) Example 3 Synthesis of N-α-methylbenzyl-N, N, N-trimethylammonium hexafluoroantimonate α-methylbenzyl chloride The title compound was obtained in the same manner as in Example 1 except that trimethylamine and sodium hexafluoroantimonate were used.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),3.1ppm(s,9H,Me),4.8ppm(q,1H,C
H),7.5−7.6ppm(m,5H,Ph) 実施例4 N−2−ヒドロキシエチル−N−p−クロロ−α−メチ
ルベンジル−N,N−ジメチルアンモニウムヘキサフルオ
ロアンチモネートの合成 p−クロロ−α−メチルベンジルクロライド,ジメチル
エタノールアミン及びソジウムヘキサフルオロアンチモ
ネートを用いて実施例1と同様の方法により表記化合物
を得た。1.7ppm (d, 3H, Me), 3.1ppm (s, 9H, Me), 4.8ppm (q, 1H, C
H), 7.5-7.6 ppm (m, 5H, Ph) Example 4 Synthesis of N-2-hydroxyethyl-N-p-chloro-α-methylbenzyl-N, N-dimethylammonium hexafluoroantimonate p-chloro The title compound was obtained in the same manner as in Example 1 using -α-methylbenzyl chloride, dimethylethanolamine and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),2.9−3.0ppm(t,6H,Me),3.1ppm
(s,6H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2H,C
H2),4.8ppm(q,1H,CH),7.5−7.6ppm(m,4H,Ph) 実施例5 N−p−メチル−α−メチルベンジル−N,N,N−トリメ
チルアンモニウムヘキサフルオロアンチモネートの合成 p−メチル−α−メチルベンジルクロライド,トリメチ
ルアミン及びソジウムヘキサフルオロアンチモネートを
用いて実施例1と同様の方法により表記化合物を得た。1.7ppm (d, 3H, Me), 2.9-3.0ppm (t, 6H, Me), 3.1ppm
(S, 6H, Me), 3.3−3.4ppm (q, 2H, CH 2 ), 3.9ppm (q, 2H, C
H 2), 4.8ppm (q, 1H, CH), 7.5-7.6ppm (m, 4H, Ph) Example 5 N-p-methyl -α- methylbenzyl -N, N, N-trimethyl ammonium hexafluoroantimonate Synthesis of nate The title compound was obtained in the same manner as in Example 1 using p-methyl-α-methylbenzyl chloride, trimethylamine and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),2.3ppm(s,3H,Me),3.1ppm(s,9H、
Me),4.8ppm(q,1H,CH),7.5−7.6ppm(m,4H,Ph) 実施例6 N−α−メチルベンジル−N,N,N−トリメチルアンモニ
ウムヘキサフルオロフォスフェートの合成 α−メチルベンジルクロライド,トリメチルアミン及び
ソジウムヘキサフルオロフォスフェートを用いて実施例
1と同様の方法により表記化合物を得た。1.7ppm (d, 3H, Me), 2.3ppm (s, 3H, Me), 3.1ppm (s, 9H,
Me), 4.8 ppm (q, 1H, CH), 7.5-7.6 ppm (m, 4H, Ph) Example 6 Synthesis of N-α-methylbenzyl-N, N, N-trimethylammonium hexafluorophosphate α- The title compound was obtained in the same manner as in Example 1 using methylbenzyl chloride, trimethylamine and sodium hexafluorophosphate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),3.1ppm(s,9H,Me),4.8ppm(q,1H,C
H),7.5−7.6ppm(m,5H,Ph) 実施例7 N−2−ヒドロキシエチル−N−p−クロロ−α−メチ
ルベンジル−N,N−ジメチルアンモニウムテトラフルオ
ロボレートの合成 p−クロロ−α−メチルベンジルクロライド,ジメチル
エタノールアミン及びソジウムテトラフルオロボレート
を用いて実施例1と同様の方法により表記化合物を得
た。1.7ppm (d, 3H, Me), 3.1ppm (s, 9H, Me), 4.8ppm (q, 1H, C
H), 7.5-7.6 ppm (m, 5H, Ph) Example 7 Synthesis of N-2-hydroxyethyl-N-p-chloro-α-methylbenzyl-N, N-dimethylammonium tetrafluoroborate p-chloro- The title compound was obtained in the same manner as in Example 1 using α-methylbenzyl chloride, dimethylethanolamine and sodium tetrafluoroborate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(d,3H,Me),2.9−3.0ppm(t,6H,Me),3.1ppm
(s,6H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2H,C
H2),4.8ppm(q,1H,CH),7.5−7.6ppm(m,4H,Ph) 実施例8 N−α−ジメチルベンジル−N,N−ジメチルアニリニウ
ムヘキサフルオロアンチモネートの合成 α−ジメチルベンジルクロライド,N,N−ジメチルアニリ
ン及びソジウムヘキサフルオロアンチモネートを用いて
実施例1と同様の方法により表記化合物を得た。1.7ppm (d, 3H, Me), 2.9-3.0ppm (t, 6H, Me), 3.1ppm
(S, 6H, Me), 3.3−3.4ppm (q, 2H, CH 2 ), 3.9ppm (q, 2H, C
H 2 ), 4.8 ppm (q, 1H, CH), 7.5-7.6 ppm (m, 4H, Ph) Example 8 Synthesis of N-α-dimethylbenzyl-N, N-dimethylanilinium hexafluoroantimonate α- The title compound was obtained in the same manner as in Example 1 using dimethylbenzyl chloride, N, N-dimethylaniline and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),3.6ppm(s,6H,Me),7.1−7.6ppm
(m,10H,Ph) 実施例9 N−2−ヒドロキシエチル−N−α−ジメチルベンジル
−N,N−ジメチルアンモニウムヘキサフルオロアンチモ
ネートの合成 α−ジメチルベンジルクロライド,N,N−ジメチルエタノ
ールアミン及びソジウムヘキサフルオロアンチモネート
を用いて実施例1と同様の方法により表記化合物を得
た。1.7ppm (s, 6H, Me), 3.6ppm (s, 6H, Me), 7.1-7.6ppm
(M, 10H, Ph) Example 9 Synthesis of N-2-hydroxyethyl-N-α-dimethylbenzyl-N, N-dimethylammonium hexafluoroantimonate α-dimethylbenzyl chloride, N, N-dimethylethanolamine and The title compound was obtained in the same manner as in Example 1 using sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),2.9−3.0ppm(t,6H,Me),3.1ppm
(s,6H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2H,C
H2),7.5−7.6ppm(m,5H,Ph) 実施例10 N−α−ジメチルベンジル−N,N,N−トリエチルアンモ
ニウムヘキサフルオロアンチモネートの合成 α−ジメチルベンジルクロライド,トリエチルアミン及
びソジウムヘキサフルオロアンチモネートを用いて実施
例1と同様の方法により表記化合物を得た。1.7ppm (s, 6H, Me), 2.9-3.0ppm (t, 6H, Me), 3.1ppm
(S, 6H, Me), 3.3−3.4ppm (q, 2H, CH 2 ), 3.9ppm (q, 2H, C
H 2 ), 7.5-7.6 ppm (m, 5H, Ph) Example 10 Synthesis of N-α-dimethylbenzyl-N, N, N-triethylammonium hexafluoroantimonate α-dimethylbenzyl chloride, triethylamine and sodium hexa The title compound was obtained in the same manner as in Example 1 using fluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),2.9−3.0ppm(t,9H,Me),3.3−3.4p
pm(q,6H,CH2),7.5−7.6ppm(m,5H,Ph) 実施例11 N−α−ジメチルベンジル−N,N,N−トリメチルアンモ
ニウムヘキサフルオロアンチモネートの合成 α−ジメチルベンジルクロライド,トリメチルアミン及
びソジウムヘキサフルオロアンチモネートを用いて実施
例1と同様の方法により表記化合物を得た。1.7ppm (s, 6H, Me), 2.9-3.0ppm (t, 9H, Me), 3.3-3.4p
pm (q, 6H, CH 2 ), 7.5-7.6ppm (m, 5H, Ph) Example 11 N-alpha-dimethyl benzyl -N, N, Synthesis of N- trimethylammonium hexafluoroantimonate alpha-dimethylbenzyl chloride The title compound was obtained in the same manner as in Example 1 except that trimethylamine and sodium hexafluoroantimonate were used.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),3.1ppm(s,9H,Me),7.5−7.6ppm
(m,5H,Ph) 実施例12 N−p−ニトロ−α−ジメチルベンジル−N,N−ジメチ
ルアニリウムヘキサフルオロアンチモネートの合成 p−ニトロ−α−ジメチルベンジルクロライド,N,N−ジ
メチルアニリン及びソジウムヘキサフルオロアンチモネ
ートを用いて実施例1と同様の方法により表記化合物を
得た。1.7ppm (s, 6H, Me), 3.1ppm (s, 9H, Me), 7.5-7.6ppm
(M, 5H, Ph) Example 12 Synthesis of N-p-nitro-α-dimethylbenzyl-N, N-dimethylanilium hexafluoroantimonate p-nitro-α-dimethylbenzyl chloride, N, N-dimethylaniline The title compound was obtained in the same manner as in Example 1 using and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),3.6ppm(s,6H,Me),7.1−7.6ppm
(m,9H,Ph) 実施例13 N−2−ヒドロキシエチル−N−p−メチル−α−ジメ
チルベンジル−N,N−ジメチルアンモニウムヘキサフル
オロアンチモネートの合成 α−ジメチルベンジルクロライド,N,N−ジメチルエタノ
ールアミン及びソジウムヘキサフルオロアンチモネート
を用いて実施例1と同様の方法により表記化合物を得
た。1.7ppm (s, 6H, Me), 3.6ppm (s, 6H, Me), 7.1-7.6ppm
(M, 9H, Ph) Example 13 Synthesis of N-2-hydroxyethyl-Np-methyl-α-dimethylbenzyl-N, N-dimethylammonium hexafluoroantimonate α-dimethylbenzyl chloride, N, N- The title compound was obtained in the same manner as in Example 1 using dimethylethanolamine and sodium hexafluoroantimonate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),2.9−3.0ppm(t,6H,Me),3.1−3.2p
pm(s,9H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2
H,CH2),7.5−7.6ppm(m,4H,Ph) 実施例14 N−2−ヒドロキシエチル−N−α−ジメチルベンジル
−N,N−ジメチルアンモニウムヘキサフルオロフォスフ
ェートの合成 α−ジメチルベンジルクロライド,N,N−ジメチルエタノ
ールアミン及びソジウムヘキサフルオロフォスフェート
を用いて実施例1と同様の方法により表記化合物を得
た。1.7ppm (s, 6H, Me), 2.9-3.0ppm (t, 6H, Me), 3.1-3.2p
pm (s, 9H, Me), 3.3−3.4ppm (q, 2H, CH 2 ), 3.9ppm (q, 2
H, CH 2 ), 7.5-7.6 ppm (m, 4H, Ph) Example 14 Synthesis of N-2-hydroxyethyl-N-α-dimethylbenzyl-N, N-dimethylammonium hexafluorophosphate α-dimethylbenzyl The title compound was obtained in the same manner as in Example 1 using chloride, N, N-dimethylethanolamine and sodium hexafluorophosphate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),2.9−3.0ppm(t,6H,Me),3.1ppm
(s,6H,Me),3.3−3.4ppm(q,2H,CH2),3.9ppm(q,2H,C
H2),7.5−7.6ppm(m,5H,Ph) 実施例15 N−α−ジメチルベンジル−N,N,N−トリエチルアンモ
ニウムテトラフルオロボレートの合成 α−ジメチルベンジルクロライド,トリエチルアミン及
びソジウルテトラフルオロボレートを用いて実施例1と
同様の方法により表記化合物を得た。1.7ppm (s, 6H, Me), 2.9-3.0ppm (t, 6H, Me), 3.1ppm
(S, 6H, Me), 3.3−3.4ppm (q, 2H, CH 2 ), 3.9ppm (q, 2H, C
H 2 ), 7.5-7.6 ppm (m, 5H, Ph) Example 15 Synthesis of N-α-dimethylbenzyl-N, N, N-triethylammonium tetrafluoroborate α-dimethylbenzyl chloride, triethylamine and sodiurtetra The title compound was obtained in the same manner as in Example 1 using fluoroborate.
この化合物のNMRスペクトルを以下に示した。The NMR spectrum of this compound is shown below.
1.7ppm(s,6H,Me),2.9−3.0ppm(t,9H,Me),3.3−3.4p
pm(q,6H,CH2),7.5−7.6ppm(m,5H,Ph)1.7ppm (s, 6H, Me), 2.9-3.0ppm (t, 9H, Me), 3.3-3.4p
pm (q, 6H, CH 2 ), 7.5-7.6ppm (m, 5H, Ph)
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 FI 技術表示箇所 C08G 65/02 NQE ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI technical display area C08G 65/02 NQE
Claims (1)
から選ばれる基であり、 R4,R5は一方が水素で他方が塩素またはメチル基から選
ばれる基であるか、または両方が塩素またはメチル基か
ら選ばれる基であり、 R6,R7,R8はメチル基,エチル基,2−ヒドロキシエチル基
またはフェニル基から選ばれる基であり、 MはAs,Sb,BまたはPであり、 Xはハロゲンであり、 nはMがBである時は4であり、他の場合は6である。1. A formula Novel benzyl ammonium salt of. In the formula, R 1 , R 2 , and R 3 are groups selected from hydrogen, chlorine, a methyl group, or a nitro group, and R 4 and R 5 are one group selected from hydrogen and the other is selected from a chlorine or methyl group. Or both are groups selected from chlorine or a methyl group, R 6 , R 7 and R 8 are groups selected from a methyl group, an ethyl group, a 2-hydroxyethyl group or a phenyl group, and M is As, Sb, B or P, X is halogen, n is 4 when M is B, and 6 otherwise.
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1142541A JPH0737426B2 (en) | 1989-06-05 | 1989-06-05 | New benzyl ammonium salt |
AU56126/90A AU627316B2 (en) | 1989-06-05 | 1990-05-31 | Antimony, arsenic, boron and phosphorous halide salts of quaternary ammonium compounds |
CA002018173A CA2018173C (en) | 1989-06-05 | 1990-06-04 | Heat-latent, cationic polymerization initiator and resin compositions containing the same |
US07/532,716 US5132377A (en) | 1989-06-05 | 1990-06-04 | Heat-latent, cationic polymerization initiator and resin compositions containing the same |
EP95100720A EP0651002A3 (en) | 1989-06-05 | 1990-06-05 | Heat-latent, cationic polymerization initiator and resin compositions containing the same. |
EP90110649A EP0401770B1 (en) | 1989-06-05 | 1990-06-05 | Heat-latent, cationic polymerization initiator and resin composition containing the same |
KR1019900008291A KR0157622B1 (en) | 1989-06-05 | 1990-06-05 | Heat-latent cationic polymerization initiator and resin composition containing the same |
DE69030600T DE69030600T2 (en) | 1989-06-05 | 1990-06-05 | Heat latent, cationic polymerization initiator and resin compositions containing the same |
AU17228/92A AU640086B2 (en) | 1989-06-05 | 1992-05-28 | Antimony, arsenic, boron and phosphorous halide salts of pyridinium compounds and resin compositions containing the same |
AU17227/92A AU640085B2 (en) | 1989-06-05 | 1992-05-28 | Antimony, arsenic, boron and phosphorous halide salts of oxazolidinium compounds and resin compositions containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1142541A JPH0737426B2 (en) | 1989-06-05 | 1989-06-05 | New benzyl ammonium salt |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0311044A JPH0311044A (en) | 1991-01-18 |
JPH0737426B2 true JPH0737426B2 (en) | 1995-04-26 |
Family
ID=15317752
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1142541A Expired - Fee Related JPH0737426B2 (en) | 1989-06-05 | 1989-06-05 | New benzyl ammonium salt |
Country Status (1)
Country | Link |
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JP (1) | JPH0737426B2 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994014754A1 (en) * | 1992-12-25 | 1994-07-07 | Nippon Soda Co., Ltd. | Novel anilinium salt compound and polymerization initiator |
DE102005040126A1 (en) * | 2005-08-25 | 2007-03-01 | Altana Electrical Insulation Gmbh | coating composition |
JP4177867B2 (en) * | 2006-10-30 | 2008-11-05 | 日本ペイント株式会社 | Photosensitive composition for recording volume hologram, recording medium using the same, and method for forming volume hologram |
-
1989
- 1989-06-05 JP JP1142541A patent/JPH0737426B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
JournalofOrganicChemistry,vol.36No.7(1971)P.984−991 |
Also Published As
Publication number | Publication date |
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JPH0311044A (en) | 1991-01-18 |
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