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Article(id=1199639743198757300, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1199639737100235003, articleNumber=null, orderNo=null, doi=10.16790/j.cnki.1009-9239.im.2023.09.007, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1661356800000, receivedDateStr=2022-08-25, revisedDate=1664035200000, revisedDateStr=2022-09-25, acceptedDate=null, acceptedDateStr=null, onlineDate=1763946003007, onlineDateStr=2025-11-24, pubDate=1695139200000, pubDateStr=2023-09-20, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763946003007, onlineIssueDateStr=2025-11-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763946003007, creator=13701087609, updateTime=1763946003007, updator=13701087609, issue=Issue{id=1199639737100235003, tenantId=1146029695717560320, journalId=1149653034449285133, year='2023', volume='56', issue='9', pageStart='1', pageEnd='107', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763946001553, creator=13701087609, updateTime=1766563671560, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1210619040956027365, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1199639737100235003, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1210619040956027366, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1199639737100235003, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=38, endPage=42, ext={EN=ArticleExt(id=1199639743609799104, articleId=1199639743198757300, tenantId=1146029695717560320, journalId=1149653034449285133, language=EN, title=Synthesis and application of low dielectric loss toughening agents, columnId=1190369066675179686, journalTitle=Insulating Materials, columnName=Material Research, runingTitle=null, highlight=null, articleAbstract=

A novel low dielectric loss toughening agent (Si-DABPA) was designed and synthesized, and its structure was characterized, then its toughening effect on bismaleimide (DFE950) was studied. The results show that the Si-DABPA and diallyl bisphenol A (DABPA) have the same reactivity to DFE950. Compared with the DFE950/DABPA cured material, the Thermal degradation resistance of the DFE950/Si-DABPA cured material increases, and the dielectric constant (Dk) and dielectric loss factor (Df) decrease at 10 GHz. Compared with the DFE950/DABPA/PPE cured material, the tensile strenght of the DFE950/Si-DABPA/PPE cured material increases, while the bending strength and impact strength change little.

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本文设计合成了一种新型低介质损耗增韧剂（Si-DABPA），并对其结构进行表征，研究了其对马来酰亚胺（DFE950）的增韧效果。结果表明：Si-DABPA和二烯丙基双酚A（DABPA）对DFE950具有相同的反应活性，与DFE950/DABPA固化物相比，DFE950/Si-DABPA固化物的耐热降解性提高，10 GHz下介电常数（Dk）和介质损耗因数（Df）有所降低。与DFE950/DABPA/PPE固化物相比，DFE950/Si-DABPA/PPE固化物的拉伸强度提高，而弯曲强度和冲击强度变化不大。

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李成武（1997-），男（汉族），河南信阳人，硕士生，主要从事高分子树脂的改性工作；

唐安斌（1968-），男（汉族），四川南充人，研究员，主要从事高性能阻燃、绝缘材料的研究。

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李成武（1997-），男（汉族），河南信阳人，硕士生，主要从事高分子树脂的改性工作；

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李成武（1997-），男（汉族），河南信阳人，硕士生，主要从事高分子树脂的改性工作；

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唐安斌（1968-），男（汉族），四川南充人，研究员，主要从事高性能阻燃、绝缘材料的研究。

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唐安斌（1968-），男（汉族），四川南充人，研究员，主要从事高性能阻燃、绝缘材料的研究。

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language=CN, orderNo=2, keyword=二烯丙基双酚A), Keyword(id=1217470067768476061, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=CN, orderNo=3, keyword=介质损耗因数), Keyword(id=1217470067848167840, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=CN, orderNo=4, keyword=增韧剂)], refs=[Reference(id=1217470070612214322, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, doi=null, pmid=null, pmcid=null, year=2017, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[1], rfOrder=0, authorNames=师剑英, journalName=null, refType=null, unstructuredReference=师剑英.浅析高频覆铜板的开发要点[C]//第十八届中国覆铜板技术·市场研讨会论文集.东莞,2017., articleTitle=浅析高频覆铜板的开发要点, refAbstract=null), Reference(id=1217470070750626361, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, doi=null, pmid=null, pmcid=null, year=2021, 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figureFileBig=Y/UwtX0qmPYkCMd6LLHkHQ==, tableContent=null), ArticleFig(id=1217470069790130702, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=EN, label=Tab.1, caption=DSC data of DFE950/DABPA and DFE950/Si-DABPA system at different heating rates, figureFileSmall=null, figureFileBig=null, tableContent=
样品β/(℃/min)Ti/℃Tp/℃Tf/℃
DFE950/DABPA5185.7239.8269.4
10206.5257.4289.2
15216.9267.6300.0
20223.0275.2306.1
DFE950/Si-DABPA5163.9228.3264.9
10177.7243.4280.7
15193.6252.3294.9
20199.1261.6300.2
), ArticleFig(id=1217470069983068692, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=CN, label=表1, caption=

不同升温速率下DFE950/DABPA和DFE950/Si-DABPA的DSC数据

, figureFileSmall=null, figureFileBig=null, tableContent=
样品β/(℃/min)Ti/℃Tp/℃Tf/℃
DFE950/DABPA5185.7239.8269.4
10206.5257.4289.2
15216.9267.6300.0
20223.0275.2306.1
DFE950/Si-DABPA5163.9228.3264.9
10177.7243.4280.7
15193.6252.3294.9
20199.1261.6300.2
), ArticleFig(id=1217470070083731991, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=EN, label=Tab.2, caption=TGA data of DFE950/DABPA and DFE950/Si-DABPA cured materials, figureFileSmall=null, figureFileBig=null, tableContent=
特征参数DFE950/DABPADFE950/Si-DABPA
5%热失重温度/℃447.5477.9
残留率(800℃)/%50.5452.24
DTG峰值速率/(%/min)-7.66-12.2
DTG峰值温度/℃460.7488.7
), ArticleFig(id=1217470070196978206, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=CN, label=表2, caption=

DFE950/DABPA和DFE950/Si-DABPA固化物的TGA数据

, figureFileSmall=null, figureFileBig=null, tableContent=
特征参数DFE950/DABPADFE950/Si-DABPA
5%热失重温度/℃447.5477.9
残留率(800℃)/%50.5452.24
DTG峰值速率/(%/min)-7.66-12.2
DTG峰值温度/℃460.7488.7
), ArticleFig(id=1217470070310224419, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1199639743198757300, language=EN, label=Tab.3, caption=Test data of mechanical properties for DFE950/DABPA/PPE and DFE950/Si-DABPA/PPE cured materials, figureFileSmall=null, figureFileBig=null, tableContent=
特征参数DFE950/DABPA/PPEDFE950/Si-DABPA/PPE
冲击强度/(kJ/m2)2.92.9
拉伸强度/MPa25.429.3
弯曲强度//MPa44.146.1
弯曲模量/MPa29723244
拉伸弹性模量/MPa12861418
断裂伸长率/%2.202.25
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DFE950/DABPA/PPE和DFE950/Si-DABPA/PPE固化物的力学性能测试数据

, figureFileSmall=null, figureFileBig=null, tableContent=
特征参数DFE950/DABPA/PPEDFE950/Si-DABPA/PPE
冲击强度/(kJ/m2)2.92.9
拉伸强度/MPa25.429.3
弯曲强度//MPa44.146.1
弯曲模量/MPa29723244
拉伸弹性模量/MPa12861418
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低介质损耗增韧剂的合成及应用研究
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李成武 1 , 邹静 2 , 周友 2 , 唐安斌 1, 2 , 马寒冰 1
绝缘材料 | 材料研究 2023,56(9): 38-42
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绝缘材料 | 材料研究 2023, 56(9): 38-42
低介质损耗增韧剂的合成及应用研究
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李成武1, 邹静2, 周友2, 唐安斌1, 2, 马寒冰1
作者信息
  • 1西南科技大学 材料科学与工程学院,四川 绵阳 621000
  • 2四川东材科技集团股份有限公司 国家绝缘材料工程技术研究中心,四川 绵阳 621000

    • 李成武（1997-），男（汉族），河南信阳人，硕士生，主要从事高分子树脂的改性工作；

    唐安斌（1968-），男（汉族），四川南充人，研究员，主要从事高性能阻燃、绝缘材料的研究。

Synthesis and application of low dielectric loss toughening agents
Chengwu LI1, Jing ZOU2, You ZHOU2, Anbin TANG1, 2, Hanbing MA1
Affiliations
  • 1School of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621000, China
  • 2National Insulating Material Engineering Research Center,Sichuan EM Technology Co., Ltd., Mianyang 621000, China
出版时间: 2023-09-20 doi: 10.16790/j.cnki.1009-9239.im.2023.09.007
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摘要
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本文设计合成了一种新型低介质损耗增韧剂（Si-DABPA），并对其结构进行表征，研究了其对马来酰亚胺（DFE950）的增韧效果。结果表明：Si-DABPA和二烯丙基双酚A（DABPA）对DFE950具有相同的反应活性，与DFE950/DABPA固化物相比，DFE950/Si-DABPA固化物的耐热降解性提高，10 GHz下介电常数（Dk）和介质损耗因数（Df）有所降低。与DFE950/DABPA/PPE固化物相比，DFE950/Si-DABPA/PPE固化物的拉伸强度提高，而弯曲强度和冲击强度变化不大。

马来酰亚胺  /  二烯丙基双酚A  /  介质损耗因数  /  增韧剂

A novel low dielectric loss toughening agent (Si-DABPA) was designed and synthesized, and its structure was characterized, then its toughening effect on bismaleimide (DFE950) was studied. The results show that the Si-DABPA and diallyl bisphenol A (DABPA) have the same reactivity to DFE950. Compared with the DFE950/DABPA cured material, the Thermal degradation resistance of the DFE950/Si-DABPA cured material increases, and the dielectric constant (Dk) and dielectric loss factor (Df) decrease at 10 GHz. Compared with the DFE950/DABPA/PPE cured material, the tensile strenght of the DFE950/Si-DABPA/PPE cured material increases, while the bending strength and impact strength change little.

maleimide  /  diallyl bisphenol A  /  dielectric loss factor  /  toughening agents
李成武, 邹静, 周友, 唐安斌, 马寒冰. 低介质损耗增韧剂的合成及应用研究. 绝缘材料, 2023 , 56 (9) : 38 -42 . DOI: 10.16790/j.cnki.1009-9239.im.2023.09.007
Chengwu LI, Jing ZOU, You ZHOU, Anbin TANG, Hanbing MA. Synthesis and application of low dielectric loss toughening agents[J]. Insulating Materials, 2023 , 56 (9) : 38 -42 . DOI: 10.16790/j.cnki.1009-9239.im.2023.09.007
正文
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0 引言
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随着电子产品向高频化、数字化、小型化以及高可靠性等方向发展，特别是5G通讯、人工智能、工业互联网等对高频高速的需求，终端设备对印制电路板（PCB）中绝缘介质层的玻璃化转变温度（Tg）、介质损耗因数（Df）、热膨胀系数（CTE）等指标提出了更高要求，这些指标在很大程度上受到所用基体树脂的影响[1-2]。马来酰亚胺作为一种性能优良的耐高温热固性树脂，具有较高的玻璃化转变温度，同时力学性能和电性能十分优良，具有介电常数低、介质损耗低等优点。但和环氧树脂一样，马来酰亚胺也存在固化物交联密度高、韧性较差的缺点，因此提高韧性是达到高技术要求和扩大新应用领域的技术关键[3-5]。
二烯丙基双酚A（DABPA）是马来酰亚胺树脂使用最广泛的一种增韧改性剂，Ciba-Ceigy公司开发的XU-292和亨斯曼公司的5292便是代表性产品，被广泛应用于PCB的生产[6]。然而DABPA分子结构上带有两个强极性羟基，使得固化物的极性和吸水率较大，介质损耗较高，无法应用于对介质损耗要求严格的场景。有机硅树脂是兼具有机基团和无机结构的半无机聚合物，与其他聚合物相比，其在耐热性、耐候性、耐湿性、绝缘性等方面都表现出优异的性能，常被用于PCB基板的生产[7]。
为解决DABPA在增韧改性马来酰亚胺中存在介质损耗偏高的问题，本文设计合成了一种新型的低介质损耗有机硅增韧剂（Si-DABPA），旨在利用DABPA和有机硅各自的优异特性，在增韧马来酰亚胺的同时，实现降低介质损耗的目的。
1 实验
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1.1 主要原材料
三甲基一氯硅烷（TMSCl）、N,N-二甲基甲酰胺（DMF）、吡啶、甲苯，分析纯，成都市科隆化学品有限公司；多马来酰亚胺（DFE950）、二烯丙基双酚A（DABPA），工业级，四川东材科技集团股份有限公司。
1.2 样品制备
低介质损耗增韧剂Si-DABPA的合成：称取60.0 g DABPA置于带有机械搅拌和温控仪的三颈烧瓶中，加入200 mL DMF搅拌溶解，接着加入30.8 g吡啶，冰浴降温至10℃以下。然后称取42.3 g TMSCl，用恒压滴液漏斗在30 min内缓慢滴入烧瓶中（温度控制为5～20℃），滴加完毕后在5～20℃搅拌反应12 h。加入200 mL甲苯，然后用50 mL水洗3次分相除去吡啶盐酸盐，最后通过减压蒸馏除去甲苯，得到目标产物低介质损耗增韧剂（Si-DABPA），合成路线如图1所示。
DFE950/Si-DABPA和DFE950/DABPA体系预聚物的制备：加入100 g DFE950于三口烧瓶中，升温至125℃熔化，加入13 g Si-DABPA或DABPA，在125℃下恒温搅拌150 min，出料得到预聚物。
试样的制备：将以上预聚物研磨成粉，根据性能测试需求置于不同规格的金属框模具中，在真空热压机中压制固化成型。压合参数：抽真空至5 985～8 710 Pa，压力为0.5～2 MPa，温度程序为175℃/1.5 h+215℃/2 h+260℃/4 h。
1.3 测试方法
红外光谱使用Nicolet5700型红外光谱仪进行测试，选用KBr压片法。
核磁共振（NMR）谱使用Bruker Avance600型核磁共振仪进行测试，以氘代氯仿（CDCl3）为溶剂，TMS内标。
DSC使用Q20型差示扫描量热仪进行测试，N2气氛，气流速度为40 mL/min，升温速率（β）分别为5、10、15、20℃/min，扫描温度为40～400℃。
TGA使用Discovery型热重分析仪进行测试，氮气氛围，升温速率为10℃/min，扫描温度为40～800℃。
拉伸强度使用UTM6205型电子万能试验机按照GB/T 1303.2—2019进行测试，速度为5 mm/min；弯曲强度使用UTM6104型电子万能试验机按照GB/T 9341—2008进行测试；冲击强度使用XJ-300A型冲击试验机按照GB/T 1303.2—2019进行测试。
介电常数（Dk）和介质损耗因数（Df）采用安捷伦公司的P9373A型网络分析仪进行测试，测试频率为10 GHz。
2 结果与讨论
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2.1 红外光谱分析
图2为DABPA和Si-DABPA的红外光谱图。由图2可以看出，3 436 cm-1附近为DABPA酚羟基的特征吸收峰；2 967 cm-1附近是-CH2-和-CH3基团上C-H的伸缩振动峰；1 637 cm-1处是-CH=CH2的伸缩振动峰；1 501 cm-1和995 cm-1处是苯环的特征吸收峰；818 cm-1处是-C=C-H-上C-H的变形振动峰[6]。在TMSCl与DABPA反应后，3 400～3 500 cm-1处酚羟基的吸收峰在Si-DABPA的红外谱图中消失。从以上分析可知，TMSCl已经引入到DABPA的两个羟基末端。
2.2 核磁共振分析
为了确定合成产物结构，对Si-DABPA进行核磁共振氢谱（1H NMR）分析，结果如图3所示。分析图3可得，1H NMR（400 MHz，CDCl3，δ）：7.06(s，2 H)，7.0(d，JHH=8.4 Hz，2 H)，6.75(d，JHH=8.4 Hz，2 H)，6.02～5.96(m，2 H)，5.08～5.04(m，4 H)，3.37(d，JHH=6.5 Hz，2 H)，1.69(s，6 H)，0.34(s，18 H)。产物结构中各个质子对应的化学位移已标注于图3中，可以看出质子化学位移和质子个数与目标化合物Si-DABPA一致。
2.3 固化动力学研究
DFE950/DABPA和DFE950/Si-DABPA体系在不同升温速率下的DSC曲线如图4～5所示。由图4～5可知，DFE950/DABPA和DFE950/Si-DABP体系在不同升温过程中出现了明显的放热峰，起始固化温度记为Ti，峰值温度记为Tp，终点温度记为Tf，并汇总于表1中。
为揭示Si-DABPA与DFE950的固化反应动力学，采用Kissinger法[8-10]计算表观活化能Ea，用Crane方程[11]计算反应级数n和表观指前因子A。
结合表1计算得到DFE950/DABPA体系的Ea为82.78 kJ/mol，反应级数n为0.90，表观指前因子A为5.06×107，得出DFE950/DABPA体系的固化反应动力学方程如式（1）所示。
dadt=5.06×1071-a0.90exp -82.78RT
结合表1计算得到DFE950/Si-DABPA体系的Ea为85.63 kJ/mol，反应级数n为0.91，表观指前因子A为1.74×108，得出DFE950/Si-DABPA体系的固化反应动力学方程式如（2）所示。
dadt=1.74×1081-a0.91exp -85.63RT
式（1）～（2）中：a为固化反应程度；T为温度；R为气体常数。
由以上DSC分析数据可知，DFE950/Si-DABPA体系的反应活性及反应级数与DFE950/DABPA体系相比并未发生显著变化，说明采用TMSCl对DABPA羟基封端改性没有对DABPA与DFE950的反应活性产生明显影响。
2.4 热性能分析
材料的耐热降解性对其使用场景有重要的影响，对DFE950/DABPA和DFE950/Si-DABPA固化物进行TGA测试，热失重曲线和相关数据如图6和表2所示。
由图6和表2可知，DFE950/Si-DABPA固化物的5%热失重温度、800℃残留率以及DTG峰值温度均比DFE950/DABPA固化物高，表明DFE950/Si-DABPA固化物的耐热降解性优于DFE950/DABPA固化物，这是由于DFE950/Si-DABPA中不含羟基结构[12]。由于Si-DABPA结构中含有大量甲基，DFE950/Si-DABPA固化物的最大降解速率（DTG峰值）比DFE950/DABPA固化物大。
2.5 电气性能分析
为了分析TMSCl对DABPA羟基封端改性后，材料介电性能的变化，分别测试了DFE950/DABPA和DFE950/Si-DABPA固化物在温度为26～29℃、湿度为46%～62%环境下保存不同时间的介电常数（Dk）和介质损耗因数（Df），结果如图7所示。
由图7可知，随着保存时间的延长，DFE950/DABPA固化物和DFE950/Si-DABPA固化物的Dk和Df都缓慢增大并趋向于平稳。在相同条件下，DFE950/Si-DABPA固化物的Dk和Df均低于DFE950/DABPA固化物，在初始条件下，DFE950/Si-DABPA固化物的Dk=2.945 98，Df=0.004 56，DFE950/DABPA固化物的Dk=3.052 39，Df=0.005 21，在保存至第10 d时，DFE950/Si-DABPA固化物的Dk=3.579 47，Df=0.021 81，DFE950/DABPA的Dk=3.683 19，Df=0.022 43。
2.6 力学性能分析
因DFE950/DABPA和DFE950/Si-DABPA固化物脆性偏大，不宜制作力学性能测试样品，采用添加质量分数为20%的聚苯醚（PPE，Mn=35 000）增韧的方式制备测试样品。DFE950/DABPA/PPE固化物和DFE950/Si-DABPA/PPE固化物的力学性能测试数据平均值如表3所示。由表3可知，DFE950/Si-DABPA/PPE固化物的冲击强度与DFE950/DABPA/PPE固化物的冲击强度相同，表明Si-DABPA保留了DABPA的增韧效果，具有与DABPA相似的增韧机理。分析认为，加热条件下Si-DABPA烯丙基结构首先与DFE950双烯加成，降低了DFE950树脂的交联度；在高温固化阶段，共轭二烯与马来酰亚胺双键生成刚性环，形成两相结构，当材料受到外力作用时，可以引发微裂纹吸收外力，从而达到增韧的目的[13-14]。在拉伸强度方面，DFE950/Si-DABPA/PPE固化物较DFE950/DABPA/PPE固化物有所提高，这可能与三甲基硅氧的柔性结构有关[15]。
3 结论
收起
本研究成功合成了一种新型的增韧改性剂Si-DABPA。DSC分析结果显示，Si-DABPA改性DFE950保留了原固化体系DFE950/DABPA的反应活性，反应活化能Ea为85.63 kJ/mol，反应级数n为0.91。相比于DFE950/DABPA固化物，DFE950/Si-DABPA固化物的5%热失重温度和DTG峰值温度有所提高，耐热降解性得到改善。介电性能方面，DFE950/Si-DABPA固化物的Dk和Df始终低于DFE950/DABPA固化物。力学性能方面，DFE950/DABPA/PPE和DFE950/Si-DABPA/PPE固化物的冲击强度和弯曲强度差异不明显，但DFE950/Si-DABPA/PPE固化物的拉伸强度较DFE950/DABPA/PPE固化物有所提高。
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2023年第56卷第9期
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doi: 10.16790/j.cnki.1009-9239.im.2023.09.007
  • 接收时间：2022-08-25
  • 首发时间：2025-11-24
  • 出版时间：2023-09-20
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  • 收稿日期：2022-08-25
  • 修回日期：2022-09-25
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    1西南科技大学 材料科学与工程学院,四川 绵阳 621000
    2四川东材科技集团股份有限公司 国家绝缘材料工程技术研究中心,四川 绵阳 621000
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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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