Page 174 - 201812

第 35 卷第 12 期 精 细 化 工 Vol.35, No.12
2018 年 12 月 FINE CHEMICALS Dec. 2018

丙烯酸系列化学品
氨基甲酸酯丙烯酸酯的合成及其光固化性能

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鲁 婷，周宏勇，王家喜
（河北工业大学 化工学院，天津 300130）

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。再利用其与 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
1
成了含多官能度氨基甲酸酯丙烯酸酯（NIPUs）。用 HNMR 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 6H。
关键词：酯交换；Michael 加成；氨基甲酸酯；丙烯酸酯系列化学品；光固化
中图分类号：TQ737 文献标识码：A 文章编号：1003-5214 (2018) 12-2142-06

Synthesis of Acrylates Containing Carbamate Groups and

Their UV Curing Properties

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LU Ting, ZHOU Hong-yong, WANG Jia-xi
（School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China）

Abstract: Ethylene carbonate respectively reacted with 1,6-hexanediamine and isophoronediamine to
produce carbamate diols. Subsequently, transesterification reactions between the resulting carbamate diols
and dimethyl malonate led to malonate terminated carbamates. Finally, a series of multifunctional acrylates
containing carbamate groups (NIPUs) were obtained by Michael addition reactions between malonate
terminated carbamates and 1,6-hexanediol diacrylate, 1,3-neopentyl glycol diacrylate and polyethylene
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glycol diacrylate, respectively. The synthesized intermediates and NIPUs were characterized by HNMR
and high resolution mass spectroscopy. The UV curing process of NIPUs was studied by FTIR and the UV
cured film properties of the synthesized multifunctional acrylates gel were preliminary evaluated. The
results showed that the multifunctional acrylate solution with 3% photoinitiator 1173 (mass fraction, based
on the total mass of the mixture, the same below) and 10% HDDA could be cured within 60 s and form
films with smooth surface and good flexibility (0.5~2.0 mm). The gel rate of the cured films was greater
than 96%. The adhesion of the cured films to glass was level 0~2. The pencil hardness of the UV cured
films based carbamate acrylates derived from HDDA and NPGDA reached 6H.
Key words: transesterification; Michael addition; carbamate; acrylate series chemicals; UV curing

涂料在国民经济中具有重要的地位，与热固化 的光固化单体，聚氨酯丙烯酸酯是一类重要的光固
涂料相比，紫外光固化涂料具有固化速度快、污染 化胶用低聚物 [2-4] ，作者曾利用异氰酸酯法合成出多
[5]
[1]
少、节能、固化产物性能优异等优点 。光固化涂 臂多官能度聚氨酯丙烯酸酯 。聚氨酯（PU）因其
料的主要成分是光固化树脂、功能性的光固化稀释 优良的性能广泛应用于泡沫、弹性体、涂料、薄膜
剂及光引发剂。含氨基甲酸酯丙烯酸酯是一类重要 和粘合剂等领域，被认为是最重要的聚合物材料之

收稿日期：2018-03-07; 定用日期：2018-05-25; DOI: 10.13550/j.jxhg.20180153
作者简介： 鲁 婷（1991—），女，硕士研究生。联系人：王家喜（1965—），男，教授，博士生导师，电话：18502263900，E-mail：
wangjiaxi@hebut.edu.cn。