CN110407712A - 一种单组分自迁移夺氢型光引发剂及其制备方法 - Google Patents
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Abstract
本发明属于感光高分子材料领域。本发明提供了一种单组分自迁移夺氢型光引发剂的制备方法,通过二乙醇胺和全氟烷基乙基丙烯酸酯迈克尔加成反应形成含氟羟基化合物,之后再以该羟基开含有环氧基团的二苯甲酮和硫杂蒽酮上的环氧合成单组分自迁移夺氢型光引发剂,大大降低了难闻的气味等问题,自由基聚合中引发剂向表面迁移大大降低氧阻聚问题。本发明提供了这种单组分自迁移夺氢型光引发剂的制备方法,反应条件温和简单,后处理简单易纯化。
Description
技术领域
本发明属于感光高分子材料领域,一种单组分自迁移夺氢型光引发剂及其制备方法。
背景技术
光固化是一种经济、环境友好的技术,由于它本身VOC释放,节能、快速等优点而得到广泛应用,在传统领域的应用如涂料、油墨、粘合剂;在高科技领域的应用如光电、激光成像、立体平版印刷。UV固化体系中光引发剂起着至关重要的作用,它们可以吸收特定波长光,产生自由基或离子活性种引发体系的聚合。小分子夺氢型光引发剂需要添加胺类助引发剂,容易引起气味,黄变等多种问题,光引发自由基聚合还存在表面氧阻聚问题。为此科研工作者为了改善或解决这些问题而发展研制了高分子引发剂和可迁移光引发剂等,其中可迁移的光引发剂可以迁移到表面大大降低表面氧阻聚问题,将小分子胺接入引发剂分子还可以改善气味问题。
发明内容
本发明要解决的技术问题是:为了解决传统小分子二苯甲酮和硫杂蒽酮类光引发剂引发自由基聚合时表面氧阻聚和小分子活性胺产生的难闻的气味等问题,通过将氟和胺组分引入光引发剂,从而达到引发剂向表面迁移降低氧阻聚、改善难闻的气味等的目的。
本发明解决技术问题采用的技术手段是一种单组分自迁移夺氢型光引发剂,其结构为:
新型单组分自迁移夺氢型光引发剂的制备反应方程式为:
所述光固化引发剂制备方法,包括如下步骤:
步骤1)将二乙醇胺放入250ml三口烧瓶中,加入乙醇作溶剂,氢氧化锂作催化剂,加入少量对羟基苯甲醚作阻聚剂,加入全氟辛基乙基丙烯酸酯,升温至30~40度,反应5.5h,蒸出乙醇;
步骤2)将含有环氧基团的二苯甲酮或硫杂蒽酮等小分子投入第一步所得产物的甲苯体系中,加入四丁基溴化铵作催化剂,升温至90度反应;
步骤3)产物以水洗,保留有机相,蒸出溶剂,并用冰乙醇重结晶。
具体地,所述R基团可以为不同夺氢型小分子光引发剂;
具体地,所述步骤1)中二乙醇胺和全氟辛基乙基丙烯酸酯物质的量之比为1:1;
具体地,所述步骤2)中含有环氧基团的二苯甲酮或硫杂蒽酮与含氟的二羟基化合物物质的量之比为2:1;
具体地,所述步骤2)中反应持续时间为0.5~2小时。
本发明的有益效果是:将氟引入光引发剂体系中,同时将活性胺组分引入引发剂分子中,合成单组分自迁移夺氢型光引发剂,这类光引发剂在体系中使用时相比于小分子夺氢型光引发剂毒性小、气味小,大大降低了对人和环境的不良影响并且大大降低了表面氧阻聚。
本发明提供了这种单组分自迁移夺氢型光引发剂的制备方法,反应过程简单,实验条件温和,后处理和纯化简单容易操作。
具体实施方式
下列实施例详细说明本发明,但并不限制本发明的范围。
实施例1:
化合物1的结构式
将二乙醇胺放入250ml三口烧瓶中,加入乙醇作溶剂,氢氧化锂作催化剂,加入少量对羟基苯甲醚作阻聚剂,加入全氟辛基乙基丙烯酸酯,升温至30~40度,反应5.5h,蒸出乙醇;将含有环氧基团的4-(2,3-环氧丙氧基)二苯甲酮小分子投入第一步所得产物的甲苯体系中,加入四丁基溴化铵作催化剂,升温至90度反应;产物以水洗,保留有机相,蒸出溶剂,并用冰乙醇重结晶。通过红外检测产物中环氧特征峰消失,说明羟基与环氧反应成功进行。
实施例2
化合物2的结构式为:
将二乙醇胺放入250ml三口烧瓶中,加入乙醇作溶剂,氢氧化锂作催化剂,加入少量对羟基苯甲醚作阻聚剂,加入全氟辛基乙基丙烯酸酯,升温至30~40度,反应5.5h,蒸出乙醇;将含有环氧基团的4-(2-(环氧甲氧基)乙氧基)二苯甲酮小分子投入第一步所得产物的甲苯体系中,加入四丁基溴化铵作催化剂,升温至90度反应;产物以水洗,保留有机相,蒸出溶剂,并用冰乙醇重结晶。
通过红外检测产物中环氧特征峰消失,说明羟基与环氧反应成功进行。
实施例3
化合物3的结构式为:
将二乙醇胺放入250ml三口烧瓶中,加入乙醇作溶剂,氢氧化锂作催化剂,加入少量对羟基苯甲醚作阻聚剂,加入全氟辛基乙基丙烯酸酯,升温至30~40度,反应5.5h,蒸出乙醇;
将含有环氧基团的4-(2,3-环氧丙氧基)硫杂蒽酮小分子投入第一步所得产物的甲苯体系中,加入四丁基溴化铵作催化剂,升温至90度反应;产物以水洗,保留有机相,蒸出溶剂,并用冰乙醇重结晶。
通过红外检测产物中环氧特征峰消失,说明羟基与环氧反应成功进行。
对比实施例4
1、配制感光性树脂组合物
按照如下比例和表1中的具体配方,配制感光树脂组合物
A:丙烯酸酯共聚物(100质量份)
B:光引发剂(5质量份)
表1-1
表1-2
实施例3 | 对比例2 | |
A | 100 | 100 |
B3(产物3) | 5 | |
B”(ITX) | 5 |
2、成膜性能测试
将上述组合物避光搅拌混合均匀后,取料于PET模板上,利用线棒涂膜,形成膜厚约10μm的涂膜,然后用汞灯光源(光强240mJ/cm2)对涂膜进行曝光,曝光时间120s,观察其是否能够固化成膜。
测试结果如表2中所示:
表2
3、自迁移性测试
分别配制上述配方,将它们分别注入模具中,固化3min,光强30mW/cm2制备得长4mm宽1mm高30mm的聚合物样条,由于引发剂中含氟而丙烯酸酯共聚物中不含氟,所以将样条从上到下截取不同的平面,以XPS表征得到的氟和碳的含量之比,用来表征引发剂的自迁移性。
测试结果如表3中表示:
表3
F:C | 实施例1 | 实施例2 | 实施例3 | 对比例1 | 对比例2 |
顶层 | 1:3.6 | 1:4.3 | 1:4.0 | 1:6.2 | 1:5.9 |
第二层 | 1:4.6 | 1:5.2 | 1:4.5 | 1:6.5 | 1:6.2 |
第三层 | 1:5.3 | 1:5.7 | 1:5.6 | 1:6.6 | 1:6.4 |
底层 | 1:7.8 | 1:8.1 | 1:8.0 | 1:6.7 | 1:6.3 |
在同等条件下,样条表面F:C比底层高,这说明本发明所制备的单组分自迁移夺氢型光引发剂可以有效的迁移向表面,降低氧阻聚,并且将小分子胺引入引发剂分子中可以降低其带来的气味黄变等问题。
Claims (5)
1.一种单组分自迁移夺氢型光引发剂及其制备方法,其特征在于包括如下步骤:
步骤1)将二乙醇胺放入250ml三口烧瓶中,加入乙醇作溶剂,氢氧化锂作催化剂,加入少量对羟基苯甲醚作阻聚剂,加入全氟辛基乙基丙烯酸酯,升温至30~40度,反应5.5h,蒸出乙醇;
步骤2)将含有环氧基团的二苯甲酮或硫杂蒽酮等小分子投入第一步所得产物的甲苯体系中,加入四丁基溴化铵作催化剂,升温至90度反应;
步骤3)产物以水洗,保留有机相,蒸出溶剂,并用冰乙醇重结晶;
所述单组分自迁移夺氢型光引发剂结构式为
R为二苯甲酮或硫杂蒽酮小分子
2.如权利要求1所述的一种单组分自迁移夺氢型光引发剂及其制备方法,其特征在于:所述含有环氧集团的小分子可以为二苯甲酮类或硫杂蒽酮类。
3.如权利要求1所述的一种单组分自迁移夺氢型光引发剂及其制备方法,其特征在于:所述步骤1)中二乙醇胺和全氟辛基乙基丙烯酸酯物质的量之比为1:1。
4.如权利要求1所述的一种单组分自迁移夺氢型光引发剂的制备方法,其特征在于:所述步骤2)中含有环氧基团的二苯甲酮或硫杂蒽酮与含氟的二羟基化合物物质的量之比为2:1。
5.如权利要求1所述的一种单组分自迁移夺氢型光引发剂的制备方法,其特征在于:所述步骤1)反应持续时间为5.5小时,所述步骤2)反应持续时间为0.5~2小时。
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CN112574615A (zh) * | 2021-01-19 | 2021-03-30 | 江苏硕茂苏彩新材料有限公司 | 一种快速固化uv油墨及其制备工艺 |
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