Bis‐substituted thiophene‐containing oxime sulfonates photoacid generators for cationic polymerization under UV–visible LED irradiation

Sun Xin; Jin Ming; Wu Xingyu; Pan Haiyan; Wan Decheng; Pu Hongting

摘要

ABSTRACT > Three novel types of thiophene‐containing oxime sulfonates with a big π‐conjugated system were reported as non‐ionic photoacid generators. The irradiation of the newly synthesized photoacid generators using near UV–visible light‐emitting diodes (LEDs) (365–475 nm) results in the cleavage of two weak N?O bonds in single molecules, which lead to the generation of different sulfonic acids in good quantum and chemical yields. The mechanism for the N?O bond cleavage for acid generation was supported by the UV–visible spectra and real‐time 1 H NMR spectra. They are developed as high‐performance photoinitiators without any additives for the cationic polymerization of epoxide and vinyl ether upon exposure to near‐UV and visible LEDs (365–475 nm) at low concentration. In the field of photopolymerization, especially visible light polymerization, it has great potential for application. ? 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56 , 776–782 </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract XMLNS =“http://www.wiley.com/namespaces/wiley”type =“main”> <title type =“main”>摘录</ title> >三种新型含噻吩氧磺酸的噻吩硫酸盐据报道，具有大π-共轭系统作为非离子光酸发生器。使用近UV可见光发光二极管（LED）（365-475nm）的新合成的光酸发生器的照射导致单分子中的两个弱N +键的切割，这导致不同磺酸的产生良好的量子和化学产率。用UV可见光光谱和实时 1-h NMR光谱支持酸产生的Nα键切割的机制。它们被开发为高性能光引发剂，没有任何用于在低浓度下暴露于接近UV和可见LED（365-475nm）时的环氧化物和乙烯基醚的阳离子聚合的添加剂。在光聚合的领域中，特别是可见光聚合，它具有很大的应用潜力。还是2018 Wiley期刊，Inc.J.Colom。 SCI。，A部分：polym。化学。 2018 </ b>， 56 </ i>，776-782 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-35621/'>《Journal of Polymer Science, Part A. Polymer Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第7期</span><b style="margin: 0 2px;">|</b><span>共7页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sun Xin&option=202" target="_blank" rel="nofollow">Sun Xin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jin Ming&option=202" target="_blank" rel="nofollow">Jin Ming;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Xingyu&option=202" target="_blank" rel="nofollow">Wu Xingyu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pan Haiyan&option=202" target="_blank" rel="nofollow">Pan Haiyan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wan Decheng&option=202" target="_blank" rel="nofollow">Wan Decheng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pu Hongting&option=202" target="_blank" rel="nofollow">Pu Hongting;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> <p>Department of Polymer Materials School of Materials Science and EngineeringTongji University 4800 Caoan RoadShanghaiz 201804 People's Republic of China;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1184.html" title="有机化学">有机化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cationic photopolymerization&option=203" rel="nofollow">cationic photopolymerization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=light‐emitting diodes&option=203" rel="nofollow">light‐emitting diodes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oxime sulfonate&option=203" rel="nofollow">oxime sulfonate;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoacid generators&option=203" rel="nofollow">photoacid generators;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoinitiators&option=203" rel="nofollow">photoinitiators;</a> </p> <div class="translation"> 机译：阳离子光聚合;发光二极管;肟磺酸盐;光偶发器;光引发剂; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704020725958.html">Bis‐substituted thiophene‐containing oxime sulfonates photoacid generators for cationic polymerization under UV–visible LED irradiation</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sun Xin&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Sun Xin,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jin Ming&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Jin Ming,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Xingyu&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Wu Xingyu,</a> <a href="/journal-foreign-35621/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Polymer Science, Part A. 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href="/academic-conference-cn_meeting-33490_thesis/02022863322.html">含阳离子取代基酞菁与甲基橙复合膜的组装及光致变色物性研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=于美香&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 于美香</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=于美荣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,于美荣</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=冯绪胜&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,冯绪胜</a> <span> <a href="/conference-cn-33490/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第三届中国功能材料及其应用学术会议 </a> <span> <span> . 1998</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311864965.html">亚铵阳离子型脱水剂制备与应用及超声波辐射下肟的还原</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=刘蕊艳&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 刘蕊艳</a> <span> . 2010</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120104250228.html">含织物柔软剂和阳离子聚酯去污聚合物的漂洗添加用织物整理剂组合物以及优选阳离子去污聚合物</a> <b>[P]</b> . <span> 中国专利： CN1048072A </span> <span> . 1990-12-26</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120104245255.html">含织物柔软剂和阳离子聚酯去污聚合物的漂洗时加入的织物整理剂以及优选阳离子去污聚合物</a> <b>[P]</b> . <span> 中国专利： CN1048060A </span> <span> . 1990-12-26</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130402367580.html">Oxime sulfonate compound, photoacid generator, resist composition, cationic polymerization initiator, and cationic polymerizable composition</a> <b>[P]</b> . <span> 外国专利：  JP6605820B2 </span> <span> . 2019-11-13</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：肟磺酸盐化合物，光酸产生剂，抗蚀剂组合物，阳离子聚合引发剂和阳离子可聚合组合物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130413376662.html">OXIME SULFONATE COMPOUND, PHOTOACID GENERATOR, RESIST COMPOSITION, CATIONIC POLYMERIZATION INITIATOR, AND CATIONIC POLYMERIZABLE COMPOSITION</a> <b>[P]</b> . <span> 外国专利：  JP2016169173A </span> <span> . 2016-09-23</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：环氧磺酸盐化合物，光酸发生剂，抗蚀剂组成，阳离子聚合引发剂和阳离子可聚合组成 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130416381984.html">OXIME SULFONATE AND N-OXYIMIDOSULFONATE PHOTOACID GENERATORS AND PHOTORESISTS COMPRISING THE SAME</a> <b>[P]</b> . <span> 外国专利：  JP2015180957A 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