巯基-烯光点击反应辅助合成多官能度蓖麻油基聚氨酯丙烯酸酯

doi:10.7517/j.issn.1674-0475.2016.02.159

影像科学与光化学 ›› 2016, Vol. 34 ›› Issue (2): 159-165.DOI: 10.7517/j.issn.1674-0475.2016.02.159

巯基-烯光点击反应辅助合成多官能度蓖麻油基聚氨酯丙烯酸酯

管晓媛, 陈广学, 何明辉

华南理工大学制浆造纸工程国家重点实验室, 广东广州 510640

收稿日期:2015-06-15 修回日期:2015-12-25 出版日期:2016-03-15 发布日期:2016-03-15
通讯作者: 陈广学

The Synthesis of Polyfunctional Castor Oil-based Polyurethane Acrylate by the Auxiliary of Thiol-ene Photo Click Reaction

GUAN Xiaoyuan, CHEN Guangxue, HE Minghui

State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, Guangdong, P. R. China

Received:2015-06-15 Revised:2015-12-25 Online:2016-03-15 Published:2016-03-15

摘要/Abstract

摘要：

研究巯基-烯光点击反应辅助合成多官能度蓖麻油基聚氨酯丙烯酸酯。首先通过光引发的巯基-烯点击反应,于蓖麻油分子上引入巯基乙醇,形成多羟基化合物,然后加入丙烯酸羟丙酯与异佛尔酮二异氰酸酯,以物质的量为1:1反应得到端异氰酸酯丙烯酸酯,最终得到蓖麻油基聚氨酯丙烯酸酯。通过调节羟基含量可以得到不同官能度的丙烯酸酯。采用红外光谱、核磁氢谱、热重分析等手段表征其结构和性能,并测试了合成的聚氨酯丙烯酸脂的吸水率、附着力等性能,同时考察了它的热稳定性。结果表明, 在紫外光照射下,巯基和不饱和双键之间发生了加成反应;该聚合物的固化膜性能得到提高,尤其是硬度和热稳定性。由本文快速合成方法得到的树脂性能良好,具有较好的应用前景,扩大了巯基-烯光点击反应在高性能UV固化材料方面的应用范围。

关键词: 巯基-烯, 光点击反应, 加成反应, 多官能度蓖麻油, 聚氨酯丙烯酸酯

Abstract:

To study the synthesis of polyfunctional castor oil-based polyurethane acrylate by the auxiliary of thiol-ene photo click reaction, first, the mercaptoethanol was introduced into castor oil via thiol-ene photo-click reaction with UV irradiation, forming polyhydroxy compounds. Then we added the isocyanate acrylate, which was obtained by the reaction between hydroxypropyl acrylate (HPA) and isophorone diisocyanate (IPDI), into polyhydroxy compounds, the molar ratio of HPA and IPDI is 1:1. Finally, we got the castor oil-based polyurethane acrylate. Different functional acrylate can be obtained by adjusting the hydroxyl content. Furthermore, the structure and performance of Polyurethane acrylate were confirmed by ¹HNMR, FT-IR and TG. The water absorption and adhesion of synthetic polyurethane acrylate were tested. Meanwhile, the thermal stability was studied. The results indicated that the thiol-ene addition reaction was proceeded and the properties of cured film are improved, especially the hardness and thermal stability. In conclusion, we report a synthetic method to prepare vegetable oil-based polyurethane acrylate (PUA) resin, and the synthetic resin has good properties, which expands the application of thiol-ene click reaction in UV curing materials.

Key words: thiol-ene, photo click reaction, addition reaction, polyfunctional castor oil, polyurethane acrylate

管晓媛, 陈广学, 何明辉. 巯基-烯光点击反应辅助合成多官能度蓖麻油基聚氨酯丙烯酸酯[J]. 影像科学与光化学, 2016, 34(2): 159-165.

GUAN Xiaoyuan, CHEN Guangxue, HE Minghui. The Synthesis of Polyfunctional Castor Oil-based Polyurethane Acrylate by the Auxiliary of Thiol-ene Photo Click Reaction[J]. Imaging Science and Photochemistry, 2016, 34(2): 159-165.

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巯基-烯光点击反应辅助合成多官能度蓖麻油基聚氨酯丙烯酸酯

The Synthesis of Polyfunctional Castor Oil-based Polyurethane Acrylate by the Auxiliary of Thiol-ene Photo Click Reaction

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