CN106279051A - 一类水性的含查耳酮‑苯并三氮唑二联体的可见光光敏剂 - Google Patents
一类水性的含查耳酮‑苯并三氮唑二联体的可见光光敏剂 Download PDFInfo
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Abstract
一类水性的含查耳酮‑苯并三氮唑二联体的可见光光敏剂，其化学通式为：其中结构式中R分别代表H,‑CN,‑N(Me)2,‑OMe。该类水性可见光光敏剂的合成步骤如下：将(2E)‑3‑[3‑(2H‑苯并三唑‑2‑基)‑4‑羟基苯基]‑1‑(4‑R基苯基)丙‑2‑烯‑1‑酮和氢氧化钠以1:1的比例加入到50mL的三口烧瓶中，加入体积为氢氧化钠50～60倍的干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到目标产物。本发明的一类水性的含查耳酮‑苯并三氮唑二联体的可见光光敏剂与4‑磺酸钠盐‑二苯甲酮共同作用，能在水性环境下引发丙烯酸类单体聚合，且具有优越的光引发效率。
Description
技术领域
本发明属涉及有高水溶性的有机盐类光敏剂领域，特别是含一类水性的含查耳酮-苯并三氮唑二联体的可见光光敏剂的合成及在水性环境下的光引发聚合应用。
背景技术
光引发材料有几个重要组分构成，包括光引发剂、光敏剂、共引发剂以及聚合单体，其中光敏剂对光聚合速度起关键性作用，决定着光聚合速率及应用范围。目前绝大多数光敏剂的水溶性不好，光引发聚合难以在水性体系中应用。
发明内容
本发明的目的是为了克服上述背景技术的不足，而合成一类水性的含查耳酮-苯并三氮唑二联体的可见光光敏剂。
本发明涉及的具有水性的含查耳酮-苯并三氮唑可见光光敏剂，其化学通式为：
R＝H,-CN,-N(Me)2,-OMe,
其中结构式中R分别代表H,-CN,-N(Me)2,-OMe。
上述含查耳酮-苯并三氮唑可见光光敏剂的合成方法如下：
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-(4-R基苯基)丙-2-烯-1-酮和氢氧化钠以1:1的比例加入到50mL的三口烧瓶中，加入体积为氢氧化钠50～60倍的干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到目标产物。
上述化合物的合成路线如下：
其中结构式中R分别代表H,-CN,-N(Me)2,-OMe。
附图说明
图1.实施例1中的2-(2H-苯并三唑-2-基)-4-[(1E)-3-羰基-3-苯基丙-1-烯-1-基]苯醇酸钠的1H核磁共振谱图(1H-NMR)；
图2.实施例2中的2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-氰基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠1H核磁共振谱图(1H-NMR)；
图3.实施例3中的2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-二甲氨基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠的1H核磁共振谱图(1H-NMR)；
图4.实施例4中的2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-甲氧基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠的1H核磁共振谱图(1H-NMR)；
图5.实施例5中的目标化合物在水中的紫外吸收光谱；
具体实施方式
下面结合实例图和附图进一步说明本发明
实施例1
2-(2H-苯并三唑-2-基)-4-[(1E)-3-羰基-3-苯基丙-1-烯-1-基]苯醇酸钠
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-苯基丙-2-烯-1-酮(0.341g,1mmol)和氢氧化钠(0.04g,1mmol)加入到50mL的三口烧瓶中，加入15mL干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到浅黄色针状晶体，产率96％，其1H核磁共振谱图如图1。1H-NMR(CDCl3-D1 500MHz)δ(ppm):7.258-7.264(d,J＝2.4Hz,1H,Ar-H),7.517-7.574(m,5H,Ar-H),7.651-7.668(m,2H,Ar-H),7.843-7.869(d,J＝14.4Hz,1H,-CH＝CH-),7.960-7.976(m,2H,Ar-H),8.052-8.064(d,J＝4.8Hz,2H,Ar-H),8.724-8.727(d,J＝1.2Hz,1H,Ar-H)。
实施例2
2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-氰基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-(4-氰基苯基)丙-2-烯-1-酮(0.366g,1mmol)和氢氧化钠(0.04g,1mmol)加入到50mL的三口烧瓶中，加入15mL干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到浅黄色固体，产率95％，其1H核磁共振谱图如图1。1H-NMR(CDCl3-D1 500MHz)δ(ppm):7.262-7.282(d,J＝10.0Hz,1H,Ar-H),7.469-7.500(d,J＝16.5Hz,1H,-CH＝CH-),7.527-7.546(m,2H,Ar-H),7.823-7.839(d,J＝8.0Hz,1H,Ar-H),7.868-7.899(m,2H,Ar-H),7.960-7.966(d,J＝16.5Hz,1H,-CH＝CH-),7.966-7.979(m,2H,Ar-H),8.113-8.130(d,J＝8.5Hz,2H,Ar-H),8.736-8.740(d,J＝2.0Hz,1H,Ar-H)。
实施例3
2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-二甲氨基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-(4-二甲氨基苯基)丙-2-烯-1-酮(0.384g,1mmol)和氢氧化钠(0.04g,1mmol)加入到50mL的三口烧瓶中，加入15mL干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到橘红色固体，产率100％，其1H核磁共振谱图如图1。1H-NMR(CDCl3-D1 500MHz)δ(ppm):3.092(s,6H,-NMe2),6.721-6.739(d,J＝4.5Hz,2H,Ar-H),7.223-7.240(d,J＝8.5Hz,1H,Ar-H),7.493-7.530(m,2H,Ar-H),7.587-7.618(d,J＝16.5Hz,1H,-CH＝CH-),7.618-7.649(m,1H,Ar-H),7.804-7.835(d,J＝16.5Hz,1H,-CH＝CH-),7.946-7.976(m,2H,Ar-H),8.036-8.054(d,J＝9.0Hz,2H,Ar-H),8.695-8.699(d,J＝2.0Hz,1H,Ar-H)。
实施例4
2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-甲氧基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-(4-甲氧基苯基)丙-2-烯-1-酮(0.371g,1mmol)和氢氧化钠(0.04g,1mmol)加入到50mL的三口烧瓶中，加入15mL干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到橘红色固体，产率96％，其1H核磁共振谱图如图1。1H-NMR(CDCl3-D1 500MHz)δ(ppm):3.912(s,3H,-OMe),7.004-7.022(d,J＝9.0Hz,2H,Ar-H),7.520-7.534(m,J＝7.0Hz,2H,Ar-H),7.562-7.593(d,1H,J＝16.5Hz,-CH＝CH-),7.650-7.670(m,1H,Ar-H),7.838-7.863(d,J＝16.5Hz,1H,-CH＝CH-),7.834-7.865(d,J＝7.75Hz,1H,Ar-H)7.967-7.986(m,2H,Ar-H),8.078-8.096(d,J＝9.0Hz,2H,Ar-H),8.731-8.734(d,J＝1.5Hz,1H,Ar-H)。
实施例5
在DMF中对4个目标化合物进行紫外吸收光谱分析，探讨其吸收波长，如图5所示。由紫外吸收光谱可知，4个化合物的最大吸收波长位于可见光区，在460nm左右，其中，有氮氮二甲基的2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-二甲氨基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠的吸收波长最大，达到509.08nm，表明这是一类可见光光敏剂。
实施例6
在100mL玻璃试管中加入2-(2H-苯并三唑-2-基)-4-[(1E)-3-羰基-3-苯基丙-1-烯-1-基]苯醇酸钠(0.239mmol,0.091g)与4-磺酸钠盐二苯甲酮(0.239mmol,0.0064g)作为光引发剂，摩尔比1:1，0.15mL三乙醇胺，5mL甲基丙烯酸甲酯(MMA)，10mL去离子水，在氙灯下滤去紫外光后，进行可见光光引发聚合，聚合物的产率为85％，表明2-(2H-苯并三唑-2-基)-4-[(1E)-3-羰基-3-苯基丙-1-烯-1-基]苯醇酸钠与4-磺酸钠盐-二苯甲酮复合，是一种优良的水性可见光光引发剂。
实施例7
在100mL玻璃试管中加入2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-氰基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠(0.239mmol,0.097g)与4-磺酸钠盐二苯甲酮(0.239mmol,0.0064g)作为光引发剂，摩尔比1:1，0.15mL三乙醇胺，5mL甲基丙烯酸甲酯(MMA)，10mL去离子水，在氙灯下滤去紫外光后，进行可见光光引发聚合，聚合物的产率为80％，表明2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-氰基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠与4-磺酸钠盐-二苯甲酮复合，是一种优良的水性可见光光引发剂。
实施例8
在100mL玻璃试管中加入2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-二甲氨基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠(0.239mmol,0.101g)与4-磺酸钠盐二苯甲酮(0.239mmol,0.0064g)作为光引发剂，摩尔比1:1，0.15mL三乙醇胺，5mL甲基丙烯酸甲酯(MMA)，10mL去离子水，在氙灯下滤去紫外光后，进行可见光光引发聚合，聚合物的产率为88％，表明2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-二甲氨基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠与4-磺酸钠盐-二苯甲酮复合，是一种优良的水性可见光光引发剂。
实施例9
在100mL玻璃试管中加入2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-甲氧基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠(0.239mmol,0.098g)与4-磺酸钠盐二苯甲酮(0.239mmol,0.0064g)作为光引发剂，摩尔比1:1，0.15mL三乙醇胺，5mL甲基丙烯酸甲酯(MMA)，10mL去离子水，在氙灯下滤去紫外光后，进行可见光光引发聚合，聚合物的产率为86％，表明2-(2H-苯并三唑-2-基)-4-[(1E)-3-(4-甲氧基苯基)-3-羰基丙-1-烯-1-基]苯醇酸钠与4-磺酸钠盐-二苯甲酮复合，是一种优良的水性可见光光引发剂。
Claims (3)
1.一类水性的含查耳酮-苯并三氮唑二联体的可见光光敏剂，其化学通式为：
R＝H,-CN,-N(Me)2,-OMe,
其中结构式中R分别代表H,-CN,-N(Me)2,-OMe。
2.如权利要求1所述的一类水性的含查耳酮-苯并三氮唑二联体的可见光光敏剂，其特征是：
该类水性可见光光敏剂的合成步骤如下：
将(2E)-3-[3-(2H-苯并三唑-2-基)-4-羟基苯基]-1-(4-R基苯基)丙-2-烯-1-酮和氢氧化钠以1:1的比例加入到50mL的三口烧瓶中，加入体积为氢氧化钠50～60倍的干燥乙醇作溶剂，常温下磁力搅拌0.5小时后，旋干，二氯甲烷洗涤，真空干燥，得到目标产物。
3.如权利要求1所述的一类水性的含查耳酮-苯并三氮唑二联体的可见光光敏剂，其用途是：该类光敏剂与4-磺酸钠盐-二苯甲酮共同作用，能在水性环境下引发丙烯酸类单体聚合，且具有优越的光引发效率。
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