氨基甲酸酯丙烯酸酯的合成及其光固化性能

Synthesis and UV curing Properties of Acrylates with Carbamate Groups

摘要:

利用碳酸亚乙酯与1,6-己二胺、异佛尔酮二胺反应合成了含氨基甲酸酯二元醇，并由氨基甲酸酯二元醇与丙二酸二甲酯的酯交换反应合成了丙二酸酯封端的氨基甲酸酯。利用丙二酸酯封端的氨基甲酸酯与1,6-己二醇二丙烯酸酯(HDDA)、1,3-新戊二醇二丙烯酸酯(NPGDA)及聚乙二醇二丙烯酸酯(PEG200DA)的Michael加成反应合成含多官能度氨基甲酸酯丙烯酸酯(NIPUs)。用1HNMR及HRMS表征了合成中间体及NIPUs的结构，用FTIR考察了NIPUs光固化过程，初步评价了合成的多官能度丙烯酸酯复配物的光固化膜性能。结果表明，含占总质量分数3 %的光引发剂1173及占总质量分数10 % HDDA的多官能度丙烯酸酯溶液均能在60 s内光固化形成表面平整、具有较好的柔韧性（0.5~2.0 mm）的膜，固化膜的凝胶率大于96 %，固化膜对玻璃的附着力为0~2级，HDDA及NPGDA基的氨基甲酸酯丙烯酸酯光固化膜的铅笔硬度均达到6 H。

Abstract:

Abstract: The 1,6-hexanediamine and isophoronediamine reacted with ethylene carbonate to produce carbamate diols, which reacted with dimethyl malonate by transesterification to form malonate terminated carbamates. The Michael addition reaction of malonate terminated carbamates with 1,6-hexanediol diacrylate,1,3-neopentyl glycol diacrylate, and polyethylene glycol diacrylate forming multifunctional acrylates containing carbamate groups (NIPUs). The structure of the synthesized intermediates and NIPUs was characterized by 1HNMR and high resolution mass spectrometry. The photo curing kinetics of NIPUs was studied by FTIR. The UV cured film properties of synthesized multifunctional acrylates gel were preliminary evaluated. The results showed that the multifunctional acrylate solution with 3% (total mass fraction) of photoinitiator 1173 and 10 % (total mass fraction) of HDDA could be cured in 60 s forming film with smooth surface and good flexibility (0.5 ~2.0 mm). The gel rate of film was reached above 96%.The adhesion of cured film to the glass was 0~2 level. The pencil hardness of UV cured film based carbamate acrylates derived from HDDA and NPGDA is up to 6 H.