JP5181624B2 - ラジカル捕捉剤、重合禁止剤および重合禁止方法 - Google Patents
ラジカル捕捉剤、重合禁止剤および重合禁止方法 Download PDFInfo
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- JP5181624B2 JP5181624B2 JP2007281714A JP2007281714A JP5181624B2 JP 5181624 B2 JP5181624 B2 JP 5181624B2 JP 2007281714 A JP2007281714 A JP 2007281714A JP 2007281714 A JP2007281714 A JP 2007281714A JP 5181624 B2 JP5181624 B2 JP 5181624B2
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- polymerization
- polymerization inhibitor
- radical scavenger
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- monomer
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- BHVPEUGTPDJECS-UHFFFAOYSA-L manganese(2+);diformate Chemical compound [Mn+2].[O-]C=O.[O-]C=O BHVPEUGTPDJECS-UHFFFAOYSA-L 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
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Landscapes
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Description
金属としては、カリウム又はナトリウムが好ましい。
(2)ハイドロキノン化合物は活性ラジカルに直接反応しない。
(3)ハイドロキノン化合物は酸素の重合禁止作用を補助している。
(2)本発明のラジカル捕捉剤はリサイクル的、触媒的に作用する。
200重量ppmメトキノン含有の市販のアクリル酸(和光純薬特級)を再結晶操作3
回実施し、メトキノンを除去した。このアクリル酸4gをガラス製の20mL試験管に入
れ、さらに、アクリル酸に対して所定量の重合禁止剤を添加し、熱伝対を液中に挿入し、ガラス製のキャピラリー管にて所定の溶存酸素濃度になるまで窒素10mL/分の流量でバブリング通気し、密封した。107℃に加熱したオイルバスに試験管を浸漬させ、内温を100℃に制御して、重合発熱による発泡するまでの時間を測定した。
常温常圧下にて、200mLのガラス製ビーカーに常温の蒸留水100gを秤り採り、
重合禁止剤10gを加え、マグネチックスターラーにて10分かくはんして観察し、次の基準で水溶性を評価する。溶解:目視で不溶分が確認できないことを意味する。不溶:目視で不溶分が確認できることを意味する。
常温常圧下にて、200mLのガラス製ビーカーに常温のトルエン(和光純薬特級)1
00gを秤り採り、重合禁止剤1gを加え、マグネチックスターラーにて10分かくはんして観察し、次の基準でトルエン溶解性を評価する。溶解:目視で不溶分が確認できないことを意味する。不溶:目視で不溶分が確認できることを意味する。なお、不溶と判定された場合は高速液体クロマトグラフィにてトルエン中の溶解度を測定した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジナトリウム50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ビス(モノメチルアンモニウム)50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ビス(モノエチルアンモニウム)50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ビス(ジメチルアンモニウム)50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ビス(トリメチルアンモニウム)50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ビス(テトラメチルアンモニウム)50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム10重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム5重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム1重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤としてヒドロキノン50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤としてメトキノン50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤を添加せず、溶存酸素濃度と誘導期間との評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム0.1重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
アクリル酸に対し、重合禁止剤として、1,2,3,4−テトラヒドロ−1,4−ジオキソ−2,3−ナフタレンジスルホン酸ジアンモニウム50重量ppmを添加し、溶存酸素濃度、誘導期間、水溶性評価およびトルエン溶解性評価を実施し、結果を表1に記載した。
Claims (5)
- 前記一般式(1)で表されるナフタレン誘導体を有効成分とする重合禁止剤。
- 請求項2に記載の重合禁止剤を使用することを特徴とするモノマーの重合禁止方法。
- 重合禁止剤の使用量がモノマーに対して1〜5000重量ppmである請求項3に記載のモノマーの重合禁止方法。
- モノマー中の溶存酸素濃度が1重量ppm以下である請求項3に記載のエチレン性不飽和モノマーの重合禁止方法。
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