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Article(id=1210613546581364815, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1210613541111984320, articleNumber=null, orderNo=null, doi=10.16790/j.cnki.1009-9239.im.2024.11.012, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1704124800000, receivedDateStr=2024-01-02, revisedDate=1710345600000, revisedDateStr=2024-03-14, acceptedDate=null, acceptedDateStr=null, onlineDate=1766562361617, onlineDateStr=2025-12-24, pubDate=1732032000000, pubDateStr=2024-11-20, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766562361617, onlineIssueDateStr=2025-12-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766562361617, creator=13701087609, updateTime=1766562361617, updator=13701087609, issue=Issue{id=1210613541111984320, tenantId=1146029695717560320, journalId=1149653034449285133, year='2024', volume='57', issue='11', pageStart='1', pageEnd='143', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1766562360313, creator=13701087609, updateTime=1766564044072, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1210620603392987671, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1210613541111984320, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1210620603392987672, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1210613541111984320, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=98, endPage=105, ext={EN=ArticleExt(id=1210613546900131928, articleId=1210613546581364815, tenantId=1146029695717560320, journalId=1149653034449285133, language=EN, title=Synthesis and properties of high heat-resistant dicyclopentadiene epoxy resin for PCB substrates, columnId=1190369066675179686, journalTitle=Insulating Materials, columnName=Material Research, runingTitle=null, highlight=null, articleAbstract=

A high heat resistant o-allylphenol-dicyclopentadiene epoxy resin was synthesized using dicyclopentadiene, o-allylphenol, and epichlorohydrin as raw materials, and its structure was characterized by infrared spectrum and gel chromatography. Then the epoxy resin was cured with bisphenol-A phenolic resin, benzoxazine resin, and active ester respectively, and a PCB substrate was pressed. The curing behavior of the system was studied by differential scanning calorimetry and thermogravimetric analysis. The mechanical properties, dielectric properties, and water absorption properties of the PCB substrate were tested, and compared with the curing system of phenol-dicyclopentadiene epoxy resin. The results show that compared with phenol-dicyclopentadiene epoxy resin, the o-allylphenol-dicyclopentadiene epoxy resin has higher heat resistance (glass transition temperature Tg and 5% thermogravimetric temperature Td5% are higher), bending strength, impact strength, high temperature bending strength retention, and better dielectric properties, lower water absorption.

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本文以双环戊二烯、邻烯丙基苯酚、环氧氯丙烷为原料，合成了高耐热的邻烯丙基苯酚-双环戊二烯环氧树脂，采用红外光谱、凝胶色谱对其结构进行表征；分别采用双酚A酚醛树脂、苯并噁嗪树脂及活性酯对环氧树脂进行固化，压制了PCB基板，采用差示扫描量热及热失重分析对体系的固化行为进行研究，测试了板材的力学性能、介电性能及吸水性能，并将其与苯酚-双环戊二烯环氧树脂的固化体系进行了对比。结果表明：邻烯丙基苯酚-双环戊二烯环氧树脂较苯酚-双环戊二烯环氧树脂具有更高的耐热性（玻璃化转变温度Tg和5%热失重温度Td5%较高）、弯曲强度、冲击强度、高温弯曲强度保持率以及更优的介电性能和更低的吸水率。

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支肖琼（1980-），女（汉族），山西平遥人，高级工程师，主要从事热固性树脂的研究；

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

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支肖琼（1980-），女（汉族），山西平遥人，高级工程师，主要从事热固性树脂的研究；

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支肖琼（1980-），女（汉族），山西平遥人，高级工程师，主要从事热固性树脂的研究；

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

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

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Research progress in low dielectric epoxy resin[C]//Proceedings of the 22nd China Copper Clad Laminate Technology Seminar. Zhuhai,2021., articleTitle=Research progress in low dielectric epoxy resin, refAbstract=null)], funds=null, companyList=[AuthorCompany(id=1218964279550726929, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, xref=1, ext=[AuthorCompanyExt(id=1218964279567504146, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, companyId=1218964279550726929, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=1School of Materials and Chemistry, Southwest University of Science and Technology, Mianyang 621000, China), AuthorCompanyExt(id=1218964279580087059, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, companyId=1218964279550726929, language=CN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=1西南科技大学 材料与化学学院，四川 绵阳 621000)]), AuthorCompany(id=1218964279705916187, 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tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Fig.8, caption=TGA curves of PDCPD-OEP and PDCOD-EP system, figureFileSmall=T2XhIgJpWqleZHEwxcAdvA==, figureFileBig=L/pTApUOfsvJCxcFsQBTlQ==, tableContent=null), ArticleFig(id=1218964287192748050, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=图8, caption=PDCPD-OEP和PDCPD-EP体系的TGA曲线, figureFileSmall=T2XhIgJpWqleZHEwxcAdvA==, figureFileBig=L/pTApUOfsvJCxcFsQBTlQ==, tableContent=null), ArticleFig(id=1218964287264051222, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 1, caption=DCPD epoxy resin curing system ratio table, figureFileSmall=null, figureFileBig=null, tableContent=
固化体系类型环氧添加量BPANBOZAE丁酮
DCPD-OEP/BPAN10045——62
DCPD-OEP/BOZ100—80—77
DCPD-OEP/AE100——8579
DCPD-EP/BPAN10036——58
DCPD-EP/BOZ100—64—70
DCPD-EP/AE100——6671
), ArticleFig(id=1218964287347937306, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表1, caption=

DCPD环氧固化体系配比表

, figureFileSmall=null, figureFileBig=null, tableContent=
固化体系类型环氧添加量BPANBOZAE丁酮
DCPD-OEP/BPAN10045——62
DCPD-OEP/BOZ100—80—77
DCPD-OEP/AE100——8579
DCPD-EP/BPAN10036——58
DCPD-EP/BOZ100—64—70
DCPD-EP/AE100——6671
), ArticleFig(id=1218964287419240478, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 2, caption=Gel permeation chromatography data of DCPD-OEP, figureFileSmall=null, figureFileBig=null, tableContent=
类型MnMw面积占比/%
Peak 11 4362 21959.341
Peak 26206214.160
Peak 35295317.094
Peak 44374385.904
Peak 53483508.088
Peak 62522548.626
Peak 71601626.786
Peak total5721 467100.000
), ArticleFig(id=1218964287528292385, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表2, caption=

DCPD-OEP凝胶渗透色谱数据

, figureFileSmall=null, figureFileBig=null, tableContent=
类型MnMw面积占比/%
Peak 11 4362 21959.341
Peak 26206214.160
Peak 35295317.094
Peak 44374385.904
Peak 53483508.088
Peak 62522548.626
Peak 71601626.786
Peak total5721 467100.000
), ArticleFig(id=1218964287641538600, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 3, caption=Physical properties of DCPD-OEP, figureFileSmall=null, figureFileBig=null, tableContent=
指标颜色性状MnMw分散系数环氧当量/(g/eq)软化点/℃
指标值棕黄色透明固体5721 4672.56433890
), ArticleFig(id=1218964287738007596, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表3, caption=

DCPD-OEP的物理性能

, figureFileSmall=null, figureFileBig=null, tableContent=
指标颜色性状MnMw分散系数环氧当量/(g/eq)软化点/℃
指标值棕黄色透明固体5721 4672.56433890
), ArticleFig(id=1218964287826087985, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 4, caption=DSC related data of PDCPD-OEP and PDCPD-EP systems, figureFileSmall=null, figureFileBig=null, tableContent=
样品Ts1/℃Tp1/℃Tf1/℃△H1/(J/g)Ts2/℃Tp2/℃Tf2/℃△H2/(J/g)Tg/℃
PDCPD-OEP/BPAN151.2197.9232.2-73.74————167.2
PDCPD-OEP/BOZ132.0181.7203.3-22.27225.0254.9282.5-70.54170.5
PDCPD-OEP/AE173.0219.4272.4-36.41————158.7
PDCPD-EP/BPAN167.8200.7228.7-116.0————132.9
PDCPD-EP/BOZ152.5184.6199.1-24.25243.8267.5286.2-129.1136.7
PDCPD-EP/AE152.6195.0222.0-119.1————127.6
), ArticleFig(id=1218964287914168374, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表4, caption=

PDCPD-OEP和PDCPD-EP体系的DSC相关数据

, figureFileSmall=null, figureFileBig=null, tableContent=
样品Ts1/℃Tp1/℃Tf1/℃△H1/(J/g)Ts2/℃Tp2/℃Tf2/℃△H2/(J/g)Tg/℃
PDCPD-OEP/BPAN151.2197.9232.2-73.74————167.2
PDCPD-OEP/BOZ132.0181.7203.3-22.27225.0254.9282.5-70.54170.5
PDCPD-OEP/AE173.0219.4272.4-36.41————158.7
PDCPD-EP/BPAN167.8200.7228.7-116.0————132.9
PDCPD-EP/BOZ152.5184.6199.1-24.25243.8267.5286.2-129.1136.7
PDCPD-EP/AE152.6195.0222.0-119.1————127.6
), ArticleFig(id=1218964288006443066, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 5, caption=TGA data of PDCPD-OEP and PDCPD-EP system, figureFileSmall=null, figureFileBig=null, tableContent=
样品Td5%/℃残留率(800℃)/%
PDCPD-OEP/BPAN361.111.94
PDCPD-OEP/BOZ351.125.23
PDCPD-OEP/AE371.516.28
PDCPD-EP/BPAN342.411.96
PDCPD-EP/BOZ329.623.96
PDCPD-EP/AE359.116.08
), ArticleFig(id=1218964288073551931, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表5, caption=

PDCPD-OEP和PDCPD-EP体系的TGA数据

, figureFileSmall=null, figureFileBig=null, tableContent=
样品Td5%/℃残留率(800℃)/%
PDCPD-OEP/BPAN361.111.94
PDCPD-OEP/BOZ351.125.23
PDCPD-OEP/AE371.516.28
PDCPD-EP/BPAN342.411.96
PDCPD-EP/BOZ329.623.96
PDCPD-EP/AE359.116.08
), ArticleFig(id=1218964288195186753, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 6, caption=The mechanical properties of PCB substrates, figureFileSmall=null, figureFileBig=null, tableContent=
基板弯曲强度纵向(常态)/MPa弯曲强度纵向(155℃)/MPa高温弯曲强度保有率/%冲击强度(简支梁)/(kJ/m2)
PDCPD-OEP/BPAN50836672113
PDCPD-OEP/BOZ53941076131
PDCPD-OEP/AE46232370110
PDCPD-EP/BPAN4672385198
PDCPD-EP/BOZ51129658107
PDCPD-EP/AE4252004792
), ArticleFig(id=1218964288337793091, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表6, caption=

PCB基板力学性能

, figureFileSmall=null, figureFileBig=null, tableContent=
基板弯曲强度纵向(常态)/MPa弯曲强度纵向(155℃)/MPa高温弯曲强度保有率/%冲击强度(简支梁)/(kJ/m2)
PDCPD-OEP/BPAN50836672113
PDCPD-OEP/BOZ53941076131
PDCPD-OEP/AE46232370110
PDCPD-EP/BPAN4672385198
PDCPD-EP/BOZ51129658107
PDCPD-EP/AE4252004792
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基板介电常数介质损耗因数
PDCPD-OEP/BPAN4.170.011 8
PDCPD-OEP/BOZ3.590.010 1
PDCPD-OEP/AE3.250.009 6
PDCPD-EP/BPAN4.310.014 8
PDCPD-EP/BOZ3.790.010 7
PDCPD-EP/AE3.360.009 9
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PCB基板介电性能测试结果

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基板介电常数介质损耗因数
PDCPD-OEP/BPAN4.170.011 8
PDCPD-OEP/BOZ3.590.010 1
PDCPD-OEP/AE3.250.009 6
PDCPD-EP/BPAN4.310.014 8
PDCPD-EP/BOZ3.790.010 7
PDCPD-EP/AE3.360.009 9
), ArticleFig(id=1218964288589451341, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=EN, label=Table 8, caption=The water absorption of PCB substrates, figureFileSmall=null, figureFileBig=null, tableContent=
基板吸水率/%基板吸水率/%
PDCPD-OEP/BPAN0.26PDCPD-EP/BPAN0.28
PDCPD-OEP/BOZ0.05PDCPD-EP/BOZ0.06
PDCPD-OEP/AE0.11PDCPD-EP/AE0.12
), ArticleFig(id=1218964288694308948, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1210613546581364815, language=CN, label=表8, caption=

PCB基板吸水性能

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基板吸水率/%基板吸水率/%
PDCPD-OEP/BPAN0.26PDCPD-EP/BPAN0.28
PDCPD-OEP/BOZ0.05PDCPD-EP/BOZ0.06
PDCPD-OEP/AE0.11PDCPD-EP/AE0.12
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PCB基板用高耐热双环戊二烯环氧树脂的合成及性能
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支肖琼 1, 2 , 唐安斌 1, 2 , 李秀云 1 , 黄杰 2 , 庞婷 2 , 廖曦 2
绝缘材料 | 材料研究 2024,57(11): 98-105
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绝缘材料 | 材料研究 2024, 57(11): 98-105
PCB基板用高耐热双环戊二烯环氧树脂的合成及性能
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支肖琼1, 2, 唐安斌1, 2, 李秀云1, 黄杰2, 庞婷2, 廖曦2
作者信息
  • 1西南科技大学 材料与化学学院，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

    • 支肖琼（1980-），女（汉族），山西平遥人，高级工程师，主要从事热固性树脂的研究；

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

Synthesis and properties of high heat-resistant dicyclopentadiene epoxy resin for PCB substrates
Xiaoqiong ZHI1, 2, Anbin TANG1, 2, Xiuyun LI1, Jie HUANG2, Ting PANG2, Xi LIAO2
Affiliations
  • 1School of Materials and Chemistry, 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: 2024-11-20 doi: 10.16790/j.cnki.1009-9239.im.2024.11.012
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摘要
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本文以双环戊二烯、邻烯丙基苯酚、环氧氯丙烷为原料，合成了高耐热的邻烯丙基苯酚-双环戊二烯环氧树脂，采用红外光谱、凝胶色谱对其结构进行表征；分别采用双酚A酚醛树脂、苯并噁嗪树脂及活性酯对环氧树脂进行固化，压制了PCB基板，采用差示扫描量热及热失重分析对体系的固化行为进行研究，测试了板材的力学性能、介电性能及吸水性能，并将其与苯酚-双环戊二烯环氧树脂的固化体系进行了对比。结果表明：邻烯丙基苯酚-双环戊二烯环氧树脂较苯酚-双环戊二烯环氧树脂具有更高的耐热性（玻璃化转变温度Tg和5%热失重温度Td5%较高）、弯曲强度、冲击强度、高温弯曲强度保持率以及更优的介电性能和更低的吸水率。

高耐热  /  邻烯丙基苯酚-双环戊二烯环氧树脂  /  力学性能  /  介电性能  /  吸水率

A high heat resistant o-allylphenol-dicyclopentadiene epoxy resin was synthesized using dicyclopentadiene, o-allylphenol, and epichlorohydrin as raw materials, and its structure was characterized by infrared spectrum and gel chromatography. Then the epoxy resin was cured with bisphenol-A phenolic resin, benzoxazine resin, and active ester respectively, and a PCB substrate was pressed. The curing behavior of the system was studied by differential scanning calorimetry and thermogravimetric analysis. The mechanical properties, dielectric properties, and water absorption properties of the PCB substrate were tested, and compared with the curing system of phenol-dicyclopentadiene epoxy resin. The results show that compared with phenol-dicyclopentadiene epoxy resin, the o-allylphenol-dicyclopentadiene epoxy resin has higher heat resistance (glass transition temperature Tg and 5% thermogravimetric temperature Td5% are higher), bending strength, impact strength, high temperature bending strength retention, and better dielectric properties, lower water absorption.

high heat resistance  /  o-allylphenol-dicyclopentadiene epoxy resin  /  mechanical properties  /  dielectric properties  /  water absorption rate
支肖琼, 唐安斌, 李秀云, 黄杰, 庞婷, 廖曦. PCB基板用高耐热双环戊二烯环氧树脂的合成及性能. 绝缘材料, 2024 , 57 (11) : 98 -105 . DOI: 10.16790/j.cnki.1009-9239.im.2024.11.012
Xiaoqiong ZHI, Anbin TANG, Xiuyun LI, Jie HUANG, Ting PANG, Xi LIAO. Synthesis and properties of high heat-resistant dicyclopentadiene epoxy resin for PCB substrates[J]. Insulating Materials, 2024 , 57 (11) : 98 -105 . DOI: 10.16790/j.cnki.1009-9239.im.2024.11.012
正文
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0 引言
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随着电子产品向微型化、轻便化和多功能化方向发展，PCB产品也越来越高密度化、高性能化，这对电子基材树脂提出了低介电常数、低介质损耗、高耐热性、低吸水率等新要求[1-2]。双环戊二烯（DCPD）环氧树脂是一类高性能环氧树脂，因结构中含有非极性的双环戊二烯骨架，增大了分子自由体积，树脂具有较好的介电性能[3]，同时脂环链具有较好的分子弹性，使其韧性提高，再结合分子结构中刚性的苯环，使得树脂兼具高耐热性等性能[4-10]，被广泛应用于高频高速覆铜板、层压板、电子油墨、IC封装等领域[11-17]。但也正是由于该树脂具有较好的韧性，其固化物刚性及耐热性略低，限制了其在载板、类载板领域的应用。为了进一步提高DCPD环氧树脂的耐热性，多数研究将萘环引入DCPD环氧树脂中[18-20]，但其原料萘酚的沸点较高（285～286℃），即使通过减压蒸馏，过量的萘酚也无法得到有效分离，使得合成的DCPD萘基环氧树脂中含有少量萘酚环氧，导致树脂的耐热性和介电性能反而下降。
针对上述不足，本文采用DCPD、邻烯丙基苯酚、环氧氯丙烷合成可进行二次交联的邻烯丙基苯酚-双环戊二烯环氧树脂（DCPD-OEP），并研究其固化行为，讨论引入双键对树脂及板材耐热性、力学性能、介电性能、吸水性等方面的影响，并将其与苯酚-双环戊二烯环氧树脂（DCPD-EP）固化体系进行对比。
1 实验
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1.1 主要原材料
DCPD、邻烯丙基苯酚、三氟化硼乙醚（BF3·Et2O）、甲醇、对苯二酚、甲苯、环氧氯丙烷（ECH）、氢氧化钠（NaOH）、二甲基咪唑，分析纯，成都市科龙化工试剂厂；活性白土，工业品，灵寿县华耀矿产品加工厂；DCPD-EP，环氧当量为261 g/eq，自制，FT-IR（KBr，νcm-1）：3 493、2 941、2 865、1 599、1 510、1 440、1 240、1 034、915、836、752 cm-1，Mn：525。双酚A酚醛树脂（BPAN），羟基当量为118 mgKOH/g，山东艾蒙特新材料有限公司；苯并噁嗪树脂（BOZ），羟基当量为218 mgKOH/g，自制；活性酯（AE，分子式如图1所示），酯基当量为225 g/eq，自制；1080电子级玻璃纤维布，九江联丰玻璃纤维有限公司。
1.2 DCPD的提纯
在装有搅拌器、温度计、冷凝管的500 mL三口烧瓶中，加入300 g DCPD粗品（纯度为90%）与0.3 g对苯二酚，开启搅拌器与真空泵，当真空度达到不高于-0.098 MPa时，开始升温，烧瓶内温度最高不超过100℃，收取80～100℃的馏出液，制得无色透明DCPD纯品（纯度为98%）。
1.3 DCPD-OPN的合成
在装有搅拌器、温度计、冷凝管、恒压滴液漏斗的500 mL四口烧瓶中通入N2，加入134.2 g（1mol）邻烯丙基苯酚及33 g（0.25mol）DCPD纯品，升温至100℃，于1 h内滴加35.1 g的BF3·Et2O的甲醇溶剂（BF3·Et2O与甲醇的质量比为1∶20）。滴加结束后，维持温度为110℃反应4 h，然后升温至140℃。在此温度下恒温1 h，降温至100℃，再加入100 mL甲苯、13 g活性白土，搅拌0.5 h。之后通过过滤除去活性白土，收集滤液。将滤液加入干净的四口烧瓶中，开启真空泵（真空度≤-0.098 MPa），温度不超过210℃，通过减压蒸馏除去过量的邻烯丙基苯酚，即得到DCPD-OPN（棕色透明固体，羟基当量为257.6 mgKOH/g，FT-IR（KBr，νcm-1）：3 427、3 042、2 957、2 878、1 592、1 488、1 454、1 231、750 cm-1），其结构式如图2所示。
1.4 DCPD-OEP的合成
在装有搅拌器、温度计、冷凝管的四口烧瓶中通入N2，加入129 g（按照0.5 mol羟基数量计算）DCPD-OPN、231 g（2.5 mol）ECH及8 g 50%NaOH溶液，将烧瓶内反应物升温至75℃搅拌3 h，然后再加入40 g 50%NaOH溶液，搅拌均匀后将反应物加热至80℃，维持此温度并反应3 h。通过减压蒸馏除去过量的ECH，加入200 mL甲苯来溶解瓶中树脂，然后降温到40℃，再加入100 g 50%NaOH溶液（分4次加入），加完后维持此温度反应2 h，直至溶液分层，保留树脂层。将树脂层水洗至pH=6～7，再旋蒸除去溶剂，最高温度不超过120℃，即制得棕黄色透明的DCPD-OEP，其结构式如图3所示。
1.5 DCPD-OEP固化物（PDCPD-OEP）的制备
将DCPD-OEP分别与BPAN、BOZ、AE、丁酮按照表1中配比混合均匀后，旋蒸除去溶剂，转入模具中，按照130℃/1 h+160℃/1 h+180℃/1 h+200℃/1 h的程序在干燥器中升温固化，然后自然冷却至室温得到DCPD固化物（PDCPD-OEP）。同时制备DCPD-EP固化物（PDCPD-EP）进行对比。
1.6 DCPD-OEP基板（PDCPD-OCCL）的制备
取12张1080玻纤布分别在表1的6种胶液中充分浸渍、烘干，形成半固化片（PP片），树脂含量RC为44%～46%。再将PP片叠合后送入压机，在温度为180～190℃和压力为8～9 MPa条件下保温保压一定时间后，即得对应的PCB基板（制作成基板以考察树脂性能），基板厚度为1.20～1.24 mm。同时以苯酚-双环戊二烯环氧树脂为原料在相同条件下制备PCB基板作为对比。
1.7 结构和性能测试
红外光谱测试采用美国PE公司生产的RX-1型红外光谱仪，采用KBr压片法，波数为500～4 000 cm-1；GPC测试采用东曹（上海）生物科技有限公司生产的HLC-8420 GPC凝胶色谱仪，以THF为流动相；DSC测试采用德国耐驰仪器公司生产的DSC 200 F3型差示扫描量热仪，升温速率为10℃/min，N2流量为20 mL/min；TGA测试采用德国耐驰仪器公司生产的TG 209 F3型热失重分析仪，升温速率为10℃/min，N2流量为30 mL/min；介电常数测试采用KEYSIGHT公司生产的P937XA USB矢量网络分析仪，测试频率为10 GHz；弯曲强度测试采用深圳三思纵横公司生产的UTM6104型电子万能试验机，按照GB/T 9341—2008相关要求进行测试；冲击强度采用吴忠材料试验机厂生产的JB6型冲击强度试验机，按照GB/T1303.2—2009相关要求进行测试；环氧当量采用瑞士万通生产的916 Ti-Touch型电位滴定仪测试；软化点采用上海昌吉生产的全自动沥青软化点试验器测试；吸水率采用梅特勒托利多公司生产的ML204/02型电子天平测试；羟基当量按照GB/T 7383—2007相关要求进行测试。
2 结果与讨论
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2.1 FTIR结构表征
2.1.1 DCPD-OPN结构表征
图4为DCPD-OPN的红外光谱。从图4可以看出，3 427 cm-1处为酚羟基的伸缩振动，3 042 cm-1处为烯丙基双键的C-H伸缩振动，2 957 cm-1和2 878 cm-1处为甲基、亚甲基的C-H伸缩振动，1 592、1 488、1 454 cm-1处为苯环的骨架振动，1 231 cm-1处为酚羟基C-O的面内弯曲振动，750 cm-1处为苯环C-H的面外弯曲振动。由此分析，本文成功合成了DCPD-OPN。
2.1.2 DCPD-OEP结构表征
图5为DCPD-OEP的红外光谱，与图4对比可以看出，3 427 cm-1处酚羟基的伸缩振动基本消失，说明DCPD-OPN反应比较充分，环氧化基本完成。在3 556 cm-1处出现了微弱的伸缩振动，说明反应生成的少量环氧环进一步发生了开环反应，形成了醇羟基。3 043 cm-1处为烯丙基双键的C-H伸缩振动，2 957 cm-1处为甲基的C-H的伸缩振动，1 599、1 490、1 452 cm-1处为苯环的骨架振动，1 241 cm-1处为烷氧基醚的伸缩振动，910、836 、751 cm-1处出现环氧环的特征吸收峰。由此分析，本文成功合成了DCPD-OEP。
2.2 凝胶色谱分析
采用凝胶色谱仪分析了DCPD-OEP的分子量分布，测试样品经过与标准样苯乙烯进行分子量比对后得到树脂分子量结果，结果如图6和表2所示（表2为图6的数据解析）。
从图6及表2可以看出，DCPD-OEP由不同聚合度、不同分子量的分子片段组成，且大分子量部分占比较高。
2.3 DCPD-OEP的物理性能
DCPD-OEP的物理性能如表3所示。从表3可以看出，该树脂具有较窄的分子量分散系数，较高的环氧当量。
2.4 PDCPD-OEP的热性能
2.4.1 DSC表征
图7为PDCPD-OEP和PDCPD-EP各固化体系的DSC测试结果，表4为各固化体系的DSC数据对比表。
从图7及表4可以看出，采用BPAN及AE的固化体系均只有1个放热峰，而采用BOZ的固化体系具有2个放热峰，这是因为BOZ属于热固性树脂，除了发生BOZ开环环氧的反应外（第1个峰），还会发生BOZ自身开环固化的反应（第2个峰）。DCPD-OEP固化体系的Ts较相应的DCPD-EP固化体系有所降低，Tf有所升高，这可能是由于DCPD-OEP双键开环的放热峰与固化剂开环环氧的放热峰叠加所致。PDCPD-OEP/BOZ固化体系的Tg为3个体系中最高，说明该体系的交联密度最高，这可能与PDCPD-OEP/BOZ体系的Ts1较低有关，在与其他体系相同的固化温度、固化时间下，PDCPD-OEP/BOZ体系的树脂反应更加充分，交联网络更加致密。另外，PDCPD-OEP固化体系的Tg较同类型PDCPD-EP固化体系高出30℃左右，这是因为PDCPD-OEP固化体系固化时不仅发生了固化剂开环环氧的反应，DCPD-OEP结构中的双键还发生了二次固化，形成了更加致密的交联结构。
2.4.2 TGA表征
PDCPD-OEP和PDCPD-EP固化体系的热稳定性测试结果如图8和表5所示。
从图8和表5可以看出，DCPD-OEP固化体系的产物均具有较高的5%热失重温度（Td5%），较DCPD-EP固化体系高出20℃左右。其中，采用AE的固化体系热失重温度最高，可能是由于C=O比O-H键、C-O键具有更大的键能所致。DCPD-OEP与DCPD-EP固化体系的800℃残留率均较低（低于30%），这可能是因为DCPD环氧的主链中含有较多的脂肪链段，其在高温下易断裂分解，导致残留率较低。值得注意的是，采用BOZ的固化体系的残留率高于其他两种体系，主要因为BOZ含有氮元素，碳氮协同起到阻燃作用[22]。具体作用机制为BOZ在分解过程中产生了含氮分子和不可燃气体，可稀释O2并抑制燃烧过程中的自由基链式反应。
2.5 PCB基板性能
2.5.1 力学性能
PCB基板的力学性能如表6所示。由表6可知，DCPD环氧压制的基板均具有较高的常态纵向弯曲强度（≥400 MPa）、冲击强度（≥80 kJ/m2）等，这主要归功于DCPD环氧结构中的双环戊二烯结构，柔韧的脂肪链给基板提供了较好的韧性。在各固化体系里，苯并噁嗪树脂固化体系压制的基板力学性能较其他固化体系基板优异，这是由于苯并噁嗪固化体系具有较高的交联密度（2.4.1中已经分析），基板固化交联网络更致密所致。PDCPD-OEP基板的力学性能优于PDCPD-EP基板，这是因为DCPD-OEP的结构中含有可以二次交联的双键，固化后的产品具有更高的交联密度。值得注意的是，PDCPD-OEP基板的高温弯曲强度保有率远高出PDCPD-EP基板，这是因为在155℃测试弯曲强度时，尚没有达到PDCPD-OEP板材的相变点，在此温度下仍可以保持较高的弯曲强度。
2.5.2 介电性能
表7为10 GHz下PCB基板的介电性能测试结果。从表7可以看出，PDCPD-EP与PDCPD-OEP板材的介电性能均较好，这主要归功于它们分子结构中的双环戊二烯环结构，增大了分子的自由体积[22]。同理，由于DCPD-OEP结构中引入了自由体积较大的烯丙基链段，导致其固化体系的介电性能优于DCPD-EP固化体系。另外，在3种固化体系中，采用活性酯（AE）的固化体系介电性能最优，这是由于活性酯与环氧基团反应后不在侧链上形成羟基，而是产生极性更小且体积更大的酯基。采用BOZ的固化体系介电性能也较好，这是由于苯并噁嗪树脂分子结构比较对称，分子极性较低，介电性能较好。采用BPAN的固化体系介电性能较差，主要是由于该固化体系中含有较多酚羟基。
2.5.3 吸水性能
表8为PCB基板的吸水性能测试结果。
从表8可以看出，采用BPAN的固化体系吸水率最高，这是由于BPAN结构中含有酚羟基，它有较强的亲水性，容易吸收空气里的水分，最终导致基板的介电性能较差。而BOZ结构虽然同样含有较多开环的酚羟基，但这些羟基可与胺Mannich桥上的N-H键或亚甲基链的C-H形成分子间和分子内氢键，保护酚羟基，阻止水汽进入，因此BOZ固化板材具有较低的吸水率。另外，从表8可以看出，由于PDCPD-OEP体系的基板中含有可二次交联的双键，交联结构更致密，吸水率较PDCPD-EP体系更低。
3 结论
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本研究成功合成了一种含双键的DCPD环氧树脂DCPD-OEP，与DCPD-EP相比，其耐热性（Tg和Td5%）、弯曲强度、冲击强度、高温弯曲强度保持率与介电性能均有提升，吸水率有所降低，表现出良好的综合性能。
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GEC L, ZHUH J, LIUM. Research progress in low dielectric epoxy resin[C]//Proceedings of the 22nd China Copper Clad Laminate Technology Seminar. Zhuhai,2021.
2024年第57卷第11期
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doi: 10.16790/j.cnki.1009-9239.im.2024.11.012
  • 接收时间：2024-01-02
  • 首发时间：2025-12-24
  • 出版时间：2024-11-20
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  • 收稿日期：2024-01-02
  • 修回日期：2024-03-14
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    1西南科技大学 材料与化学学院，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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