Synthesis and radical polymerization properties of thermal radical initiators based on        <i xmlns='http://www.wiley.com/namespaces/wiley'>oo        ‐imino‐isourea: The effect of the alkyl side chain on the radical initiation temperature

Lee Kyu Cheol; Jeong Su Bin; Kim Dong Yeon; Lee Tae Hee; Kim Soon Cheon; Kim Jin Chul; Lee Sang‐Ho; Noh Seung Man; Park Young Il

摘要

ABSTRACT > Four types of thermal radical initiators (TRIs) that are based on o ‐imino‐isourea with cyclohexyl and isopropyl groups were successfully synthesized, namely, C‐HexDCC, DiiprDCC, C‐HexDIC, and DiiprDIC. The free radical polymerization and thermal properties of those synthesized TRIs were determined via differential scanning calorimetry (DSC) (using n ‐butyl acrylate) and thermogravimetric analysis (TGA), respectively. The TRI derivatives showed peak temperatures ( T <sub>max</sub> ) from 89 to 97 °C in n ‐butyl acrylate, and DiiprDIC, with isopropyl groups on both sides of the N?O group, showed the lowest peak temperatures. The rates of N?O bond homolysis ( k <sub>d</sub> ) of all the TRIs were calculated from their half‐lives determined using real‐time nuclear magnetic resonance (NMR) spectroscopy, and their theoretical bond dissociation energies (BDEs) were calculated using density functional theory (DFT) calculations. The free radical polymerization of n ‐butyl acrylate using each TRI was efficiently determined from T <sub>peak</sub> of the DSC curves; conversions depending on polymerization temperature (80, 90, and 100 °C) were monitored to observe kinetic information of TRIs during polymerization. Furthermore, to investigate the use of TRIs in curing, we applied them to an automotive clear coating system and monitored the real‐time evolution of the elastic modulus ( G ′) during thermal curing using a rheometer for representative DiiprDIC. ? 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018 , 56 , 1749–1756 </ </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”>抽象</ title> >四种类型的热自由派启动器（tris）基于 O> -Imino-Isourea，成功合成了环己基和异丙基，即C-六己二酮，DIIPRDCC，C-六己基和DIIPRDIC。通过差示扫描量热法（DSC）测定合成的TRI的自由基聚合和热性质，分别测定（使用丙烯酸丁酯）和热重分析（TGA）。三种衍生物在丙烯酸酯中的89至97℃下显示峰值温度（ T </ i> <sum> max <sub>），丙烯酸丁酯和二普基乙酸，上面N 2 o组的两侧显示出最低的峰值温度。所有TRIS的N？O键均匀（ k </ i> <亚> d <sub> d <sub> d <sub> d <sub>）从使用实时核磁共振（NMR）光谱法测定的半衰期来计算，并且使用密度泛函理论（DFT）计算计算其理论键解离子能量（BDES）。使用每个三烷基酯的丙烯酸丁酯的自由基聚合是有效的，从DSC曲线的<亚>峰值</ sub>有效地测定了每个TR1的丙烯酸酯;根据聚合温度（80,90和100℃）的转化监测，以观察聚合过程中TRI的动力学信息。此外，为了研究TRIS在固化中的使用，我们将它们施加到汽车透明涂层系统中，并在使用流变仪进行代表的流变仪期间监测在热固化过程中的弹性模量（ g </ i>'）的实时演变Diiprdic。还是2018 Wiley期刊，Inc.J.Colom。 SCI。，A部分：polym。化学。 2018 </ b>， 56 </ i>，1749-1756 </ p> </ </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15期</span><b style="margin: 0 2px;">|</b><span>共9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=Lee Kyu Cheol&option=202" target="_blank" rel="nofollow">Lee Kyu Cheol;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Jeong Su Bin&option=202" target="_blank" rel="nofollow">Jeong Su Bin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kim Dong Yeon&option=202" target="_blank" rel="nofollow">Kim Dong Yeon;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Tae Hee&option=202" target="_blank" rel="nofollow">Lee Tae Hee;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kim Soon Cheon&option=202" target="_blank" rel="nofollow">Kim Soon Cheon;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kim Jin Chul&option=202" target="_blank" rel="nofollow">Kim Jin Chul;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Sang‐Ho&option=202" target="_blank" rel="nofollow">Lee Sang‐Ho;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Noh Seung Man&option=202" target="_blank" rel="nofollow">Noh Seung Man;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Park Young Il&option=202" target="_blank" rel="nofollow">Park Young Il;</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>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Department of Chemical EngineeringUlsan National Institute of Science and Technology (UNIST)Ulsan 44919 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</p> <p>Research Center for Green Fine Chemicals Korea Research Institute of Chemical TechnologyUlsan 44412 Republic of Korea;</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=DFT calculation&option=203" rel="nofollow">DFT calculation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=dissociation constant&option=203" rel="nofollow">dissociation constant;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=free radical polymerization&option=203" rel="nofollow">free radical polymerization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=o ‐imino‐isourea&option=203" rel="nofollow">o ‐imino‐isourea;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=thermal radical initiators&option=203" rel="nofollow">thermal radical initiators;</a> </p> <div class="translation"> 机译：DFT计算;解离常数;自由基聚合;o-inimino-Isourea;热自由基引发剂; 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target="_blank" rel="nofollow" class="tuijian_authcolor"> . 高分子材料科学与工程 </a> </span> <span> . 2005</span><span>,第3期</span> </span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chemical-reaction-engineering-technology_thesis/0201247411929.html">油溶性引发剂引发细乳液聚合中初级自由基的脱吸--水相自由基捕捉剂FeCl3的应用</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=尚玥&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 尚玥</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=单国荣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,单国荣</a> <span> <a href="/journal-cn-9160/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 化学反应工程与工艺 </a> </span> <span> . 2015</span><span>,第002期</span> </span> </div> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-journal-cn_journal-changchun-university-science-technology-natural-edition_thesis/0201247959634.html">侧链液晶高聚物的活性/可控自由基聚合</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=曹健&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 曹健</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张可达&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张可达</a> <span> <a href="/journal-cn-4512/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 长春理工大学学报（自然科学版） </a> </span> <span> . 2005</span><span>,第002期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_natural-science-journal-hainan-university_thesis/0201277476449.html">带不同侧链的含L-DOPA环二肽的合成及其DPPH自由基清除活性的测试</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=何延淼&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 何延淼</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张小燕&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张小燕</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=赵露露&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,赵露露</a> <span> <a href="/journal-cn-4609/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 海南大学学报（自然科学版） </a> </span> <span> . 2019</span><span>,第004期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-58765_thesis/020222545774.html">新型反向原子转移自由基聚合(RATRP)引发体系引发MMA“活性”自由基聚合</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=秦东奇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 秦东奇</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=钦曙辉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,钦曙辉</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=丘坤元&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,丘坤元</a> <span> <a href="/conference-cn-58765/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化学会2000年学术会议 </a> <span> <span> . 2000</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020313168542.html">功能性偶氮侧链嵌段和星型聚合物的活性自由基聚合法合成及性能研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张磊&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张磊</a> <span> . 2009</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120104678152.html">具有缩水甘油基或烷基羰基基团的N－烷氧基－4,4－二氧基－多烷基－哌啶化合物作为受控自由基聚合的官能引发剂</a> <b>[P]</b> . <span> 中国专利： CN1481363A </span> <span> . 2004-03-10</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120105079300.html">一种自由基引发剂以及该引发剂和自由基聚合树脂的混合物</a> <b>[P]</b> . <span> 中国专利： CN1887914A </span> <span> . 2007-01-03</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130485002857.html">A method for producing benzodiazepine 1 derivatives, a method for producing new phosphorylated benzodiazepine derivatives with valuable pharmacological properties is proposed. The method using the known benzodiazepine reaction chemistry makes it possible to obtain new patterns that have been used by other patterns, it is a pattern, it is a pattern, it was a pattern, it was a pattern, it was a pattern, it was a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a pattern, a heading, a hint, a diaphragm, a, etc. to obtain 10-benzodiazepine derivatives of the general formula Cs denotes a linear or branched alkyl radical containing 1–3 carbon atoms; n is an integer 1— , is that o-aminobenzophenone of the general formula 15 (Oi ^ kPlRslr 'NH OO • R where RI and R2 represent the same or different substituents and denote a hydrogen atom, halogen, nitro group or trifluoromethyl radical, in addition, Rz can also be a linear or branched al</a> <b>[P]</b> . <span> 外国专利：  SU425398A3 </span> <span> . 1974-04-25</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：提出了一种生产苯并二氮杂卓1衍生物的方法，一种生产具有有价值的药理特性的新的磷酸化苯并二氮杂卓衍生物的方法。使用已知的苯并二氮杂reaction反应化学的方法可以得到其他图案已经使用的新图案，它是一个图案，它是一个图案，它是一个图案，它是一个图案，它是一个图案，图案，图案，图案，图案，图案，图案，图案，图案，图案，图案，图案，图案，标题，提示，隔膜，等，以获得10-通式Cs的苯并二氮杂衍生物表示含有1-3个碳原子的直链或支链烷基。 n为整数1，是通式15的邻氨基二苯甲酮（Oi ^ kPlRslr'NH OO•R，其中RI和R2表示相同或不同的取代基，表示氢原子，卤素，硝基或三氟甲基，另外，Rz也可以是线性或支链的 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130427027153.html">UV CURABLE RESIN COMPOSITION HAVING IMPROVED SURFACE HARDENING PROPERTY AND DEPTH HARDENING PROPERTY BY SIMULTANEOUSLY CONTAINING A CARBAZOLE-PHENONE BASED RADICAL PHOTOPOLYMERIZATION INITIATOR AND A THERMOSETTING INITIATOR</a> <b>[P]</b> . <span> 外国专利：  KR20100066766A </span> <span> . 2010-06-18</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：通过同时包含基于咔唑-苯酚的自由基光聚合反应引发剂和热固化引发剂，可改善表面硬化性能和深度硬化性能的紫外线固化树脂组合物 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130441111679.html">MACROMONOMER DERIVED FROM NORBORNENE-BASED MONOMER HAVING HALOGEN GROUP CAPABLE OF INDUCING RADICAL POLYMERIZATION AT ITS TERMINAL, NORBORNENE POLYMER HAVING GROUP CAPABLE OF INDUCING RADICAL POLYMERIZATION AT SIDE CHAIN AND NORBORNENE POLYMER PRODUCED BY GRAFT REACTION OF THE MACROMONOMER USING ACRYLATE MONOMER OR STYRENE MONOMER, AND METHOD FOR PRODUCING THEM</a> <b>[P]</b> . <span> 外国专利：  JP2005126598A </span> <span> . 2005-05-19</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：从基于降冰片烯的单体衍生的大分子单体具有能够在其末端引发自由基聚合的卤代基团，降冰片烯聚合物的基团能够在单体链上通过单体或单体的聚合反应在单体的链上引发自由基聚合，并通过单体或缩聚反应使之还原用于生产它们 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: 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Synthesis and radical polymerization properties of thermal radical initiators based on oo ‐imino‐isourea: The effect of the alkyl side chain on the radical initiation temperature

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