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Article(id=1203281568866476825, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1203281560800830004, articleNumber=null, orderNo=null, doi=10.16790/j.cnki.1009-9239.im.2025.05.006, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1720540800000, receivedDateStr=2024-07-10, revisedDate=1724169600000, revisedDateStr=2024-08-21, acceptedDate=null, acceptedDateStr=null, onlineDate=1764814281908, onlineDateStr=2025-12-04, pubDate=1747670400000, pubDateStr=2025-05-20, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1764814281908, onlineIssueDateStr=2025-12-04, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1764814281908, creator=13701087609, updateTime=1764814281908, updator=13701087609, issue=Issue{id=1203281560800830004, tenantId=1146029695717560320, journalId=1149653034449285133, year='2025', volume='58', issue='5', pageStart='1', pageEnd='144', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=0, articleOrder=1, issueType=-1, specialIssue=null, createTime=1764814279985, creator=13701087609, updateTime=1764814963861, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1203284429251784784, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1203281560800830004, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1203284429251784785, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1203281560800830004, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=42, endPage=48, ext={EN=ArticleExt(id=1203281569239769900, articleId=1203281568866476825, tenantId=1146029695717560320, journalId=1149653034449285133, language=EN, title=Research on synthesis of low dielectric loss reactive phosphorus-containing flame retardants and properties of its epoxy composite materials, columnId=1190369066675179686, journalTitle=Insulating Materials, columnName=Material Research, runingTitle=null, highlight=

A flame retardant monomer 6-(2,5-bis ((4-vinylbenzyl) oxy) phenyl) dibenzo [c,e][1,2] phosphono-6-oxide (DOPVB) was synthesized by using 10-(2,5-dihydroxyphenyl)-10-hydro-9-oxy-10-phosphophenanthrene-10-oxide (DOPO-HQ) and 4-chloromethyl styrene (VBC) as raw materials. The DOPVB flame retardant was compounded with epoxy resin (EP) to prepare EP/DOPVB composites with different phosphorus contents, and their thermal, flame retardant, and dielectric properties were tested. The results show that the optimal synthesis conditions for DOPVB is that the molar ratio of reactants DOPO-HQ, VBC, and K2CO3 is 1∶2.2∶3.0, and the reaction time is 6 hours, then the yield is 74.55%. The EP/DOPVB cured material with a phosphorus content of 2.5% has the best comprehensive performance, its glass transition temperature is 130.4℃, which is 45.21% higher than that of pure EP. The dielectric constant is 2.98 and the dielectric loss factor is 0.005 03, which is 21.99% and 72.16% lower than that of pure EP, respectively. The vertical combustion test of the composite material prepared from the cured material reaches V-0 level, with a limit oxygen index of 67.4%.

, articleAbstract=

A flame retardant monomer 6-(2,5-bis ((4-vinylbenzyl) oxy) phenyl) dibenzo [c,e][1,2] phosphono-6-oxide (DOPVB) was synthesized by using 10-(2,5-dihydroxyphenyl)-10-hydro-9-oxy-10-phosphophenanthrene-10-oxide (DOPO-HQ) and 4-chloromethyl styrene (VBC) as raw materials. The DOPVB flame retardant was compounded with epoxy resin (EP) to prepare EP/DOPVB composites with different phosphorus contents, and their thermal, flame retardant, and dielectric properties were tested. The results show that the optimal synthesis conditions for DOPVB is that the molar ratio of reactants DOPO-HQ, VBC, and K2CO3 is 1∶2.2∶3.0, and the reaction time is 6 hours, then the yield is 74.55%. The EP/DOPVB cured material with a phosphorus content of 2.5% has the best comprehensive performance, its glass transition temperature is 130.4℃, which is 45.21% higher than that of pure EP. The dielectric constant is 2.98 and the dielectric loss factor is 0.005 03, which is 21.99% and 72.16% lower than that of pure EP, respectively. The vertical combustion test of the composite material prepared from the cured material reaches V-0 level, with a limit oxygen index of 67.4%.

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以10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物（DOPO-HQ）与4-氯甲基苯乙烯（VBC）为原料合成了6-(2,5-双((4-乙烯基苄基)氧基)苯基)二苯并[c,e][1,2]氧膦-6-氧化物（DOPVB）阻燃剂单体，将DOPVB阻燃剂与环氧树脂（EP）进行复配，制备得到不同磷含量的EP/DOPVB复合材料，并对其进行热学、阻燃和介电性能测试。结果表明：DOPVB的最佳合成条件为反应物DOPO-HQ、VBC与K2CO3的物质的量之比为1∶2.2∶3.0，反应时间为6 h，此时产率为74.55%。磷含量为2.5%的EP/DOPVB固化物综合性能最优，其玻璃化转变温度为130.4℃，较纯EP提高了45.21%；介电常数为2.98，介质损耗因数为0.005 03，较纯EP分别降低了21.99%和72.16%；该固化物制备得到的复合材料垂直燃烧测试达到V-0等级，极限氧指数为67.4%。

, articleAbstract=

以10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物（DOPO-HQ）与4-氯甲基苯乙烯（VBC）为原料合成了6-(2,5-双((4-乙烯基苄基)氧基)苯基)二苯并[c,e][1,2]氧膦-6-氧化物（DOPVB）阻燃剂单体，将DOPVB阻燃剂与环氧树脂（EP）进行复配，制备得到不同磷含量的EP/DOPVB复合材料，并对其进行热学、阻燃和介电性能测试。结果表明：DOPVB的最佳合成条件为反应物DOPO-HQ、VBC与K2CO3的物质的量之比为1∶2.2∶3.0，反应时间为6 h，此时产率为74.55%。磷含量为2.5%的EP/DOPVB固化物综合性能最优，其玻璃化转变温度为130.4℃，较纯EP提高了45.21%；介电常数为2.98，介质损耗因数为0.005 03，较纯EP分别降低了21.99%和72.16%；该固化物制备得到的复合材料垂直燃烧测试达到V-0等级，极限氧指数为67.4%。

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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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黄俊怡（1999-），女（汉族），四川广汉人，硕士生，主要从事低介质损耗阻燃材料的研究；

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黄俊怡（1999-），女（汉族），四川广汉人，硕士生，主要从事低介质损耗阻燃材料的研究；

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黄俊怡（1999-），女（汉族），四川广汉人，硕士生，主要从事低介质损耗阻燃材料的研究；

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样品DOPVB/gEP/g活性酯/g磷含量/%
EP045550
EP/DOPVB-0.5941500.5
EP/DOPVB-1.01837451.0
EP/DOPVB-1.52733401.5
EP/DOPVB-2.03629352.0
EP/DOPVB-2.54525302.5
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EP/DOPVB复合材料的配方

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样品DOPVB/gEP/g活性酯/g磷含量/%
EP045550
EP/DOPVB-0.5941500.5
EP/DOPVB-1.01837451.0
EP/DOPVB-1.52733401.5
EP/DOPVB-2.03629352.0
EP/DOPVB-2.54525302.5
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样品名称UL 94测试LOI/%
t1/st2/s滴落现象等级
EPBTBT无NR30.0
EP/DOPVB-0.5148无NR49.5
EP/DOPVB-1.0133无NR49.6
EP/DOPVB-1.5113无V-166.6
EP/DOPVB-2.015无V-065.8
EP/DOPVB-2.516无V-067.4
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EP/DOPVB复合材料的燃烧性能

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样品名称UL 94测试LOI/%
t1/st2/s滴落现象等级
EPBTBT无NR30.0
EP/DOPVB-0.5148无NR49.5
EP/DOPVB-1.0133无NR49.6
EP/DOPVB-1.5113无V-166.6
EP/DOPVB-2.015无V-065.8
EP/DOPVB-2.516无V-067.4
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样品名称T5%/℃Tmax/℃残炭率/%Dmax/(%/min)Tg/℃
EP340.7411.020.341.5889.8
EP/DOPVB-0.5347.8403.830.781.12104.9
EP/DOPVB-1.0372.0406.537.871.00124.4
EP/DOPVB-1.5364.8403.642.590.85129.2
EP/DOPVB-2.0373.2402.048.560.79130.4
EP/DOPVB-2.5373.6403.043.750.76130.4
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EP/DOPVB固化物的热分析数据

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样品名称T5%/℃Tmax/℃残炭率/%Dmax/(%/min)Tg/℃
EP340.7411.020.341.5889.8
EP/DOPVB-0.5347.8403.830.781.12104.9
EP/DOPVB-1.0372.0406.537.871.00124.4
EP/DOPVB-1.5364.8403.642.590.85129.2
EP/DOPVB-2.0373.2402.048.560.79130.4
EP/DOPVB-2.5373.6403.043.750.76130.4
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样品名称Dk(10 GHz)Df(10 GHz)
EP3.820.018 07
EP/DOPVB-0.53.250.005 61
EP/DOPVB-1.03.220.005 19
EP/DOPVB-1.53.190.005 14
EP/DOPVB-2.03.070.005 09
EP/DOPVB-2.52.980.005 03
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EP/DOPVB固化物的介电性能

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样品名称Dk(10 GHz)Df(10 GHz)
EP3.820.018 07
EP/DOPVB-0.53.250.005 61
EP/DOPVB-1.03.220.005 19
EP/DOPVB-1.53.190.005 14
EP/DOPVB-2.03.070.005 09
EP/DOPVB-2.52.980.005 03
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低介质损耗反应型含磷阻燃剂的合成及其环氧复合材料的性能研究
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黄俊怡 1 , 邹静 2 , 周友 2 , 周元林 1 , 唐安斌 1, 2
绝缘材料 | 材料研究 2025,58(5): 42-48
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绝缘材料 | 材料研究 2025, 58(5): 42-48
低介质损耗反应型含磷阻燃剂的合成及其环氧复合材料的性能研究
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黄俊怡1, 邹静2, 周友2, 周元林1, 唐安斌1, 2
作者信息
  • 1.西南科技大学 材料与化学学院，四川 绵阳 621010
  • 2.四川东材科技集团股份有限公司，四川 绵阳 621024

    • 黄俊怡（1999-），女（汉族），四川广汉人，硕士生，主要从事低介质损耗阻燃材料的研究；

通讯作者:

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。
Research on synthesis of low dielectric loss reactive phosphorus-containing flame retardants and properties of its epoxy composite materials
Junyi HUANG1, Jing ZOU2, You ZHOU2, Yuanlin ZHOU1, Anbin TANG1, 2
Affiliations
  • 1. School of Materials and Chemistry, Southwest University of Science and Technology, Mianyang 621010, China
  • 2. Sichuan EM Technology Co., Ltd., Mianyang 621024, China
出版时间: 2025-05-20 doi: 10.16790/j.cnki.1009-9239.im.2025.05.006
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摘要
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以10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物（DOPO-HQ）与4-氯甲基苯乙烯（VBC）为原料合成了6-(2,5-双((4-乙烯基苄基)氧基)苯基)二苯并[c,e][1,2]氧膦-6-氧化物（DOPVB）阻燃剂单体，将DOPVB阻燃剂与环氧树脂（EP）进行复配，制备得到不同磷含量的EP/DOPVB复合材料，并对其进行热学、阻燃和介电性能测试。结果表明：DOPVB的最佳合成条件为反应物DOPO-HQ、VBC与K2CO3的物质的量之比为1∶2.2∶3.0，反应时间为6 h，此时产率为74.55%。磷含量为2.5%的EP/DOPVB固化物综合性能最优，其玻璃化转变温度为130.4℃，较纯EP提高了45.21%；介电常数为2.98，介质损耗因数为0.005 03，较纯EP分别降低了21.99%和72.16%；该固化物制备得到的复合材料垂直燃烧测试达到V-0等级，极限氧指数为67.4%。

无卤阻燃剂  /  反应型阻燃剂  /  阻燃性能  /  介电性能

A flame retardant monomer 6-(2,5-bis ((4-vinylbenzyl) oxy) phenyl) dibenzo [c,e][1,2] phosphono-6-oxide (DOPVB) was synthesized by using 10-(2,5-dihydroxyphenyl)-10-hydro-9-oxy-10-phosphophenanthrene-10-oxide (DOPO-HQ) and 4-chloromethyl styrene (VBC) as raw materials. The DOPVB flame retardant was compounded with epoxy resin (EP) to prepare EP/DOPVB composites with different phosphorus contents, and their thermal, flame retardant, and dielectric properties were tested. The results show that the optimal synthesis conditions for DOPVB is that the molar ratio of reactants DOPO-HQ, VBC, and K2CO3 is 1∶2.2∶3.0, and the reaction time is 6 hours, then the yield is 74.55%. The EP/DOPVB cured material with a phosphorus content of 2.5% has the best comprehensive performance, its glass transition temperature is 130.4℃, which is 45.21% higher than that of pure EP. The dielectric constant is 2.98 and the dielectric loss factor is 0.005 03, which is 21.99% and 72.16% lower than that of pure EP, respectively. The vertical combustion test of the composite material prepared from the cured material reaches V-0 level, with a limit oxygen index of 67.4%.

halogen-free flame retardants  /  reactive flame retardants  /  flame retardant properties  /  dielectric properties
黄俊怡, 邹静, 周友, 周元林, 唐安斌. 低介质损耗反应型含磷阻燃剂的合成及其环氧复合材料的性能研究. 绝缘材料, 2025 , 58 (5) : 42 -48 . DOI: 10.16790/j.cnki.1009-9239.im.2025.05.006
Junyi HUANG, Jing ZOU, You ZHOU, Yuanlin ZHOU, Anbin TANG. Research on synthesis of low dielectric loss reactive phosphorus-containing flame retardants and properties of its epoxy composite materials[J]. Insulating Materials, 2025 , 58 (5) : 42 -48 . DOI: 10.16790/j.cnki.1009-9239.im.2025.05.006
正文
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0 引言
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随着电子信息技术向高集成度、高频高速方向发展，对先进电子材料的性能提出了更高的要求[1-6]。环氧树脂（EP）具有出色的绝缘性能、耐溶剂性能和力学性能，广泛应用于电子封装、电器绝缘、电子通讯、医疗建筑以及航空航天等领域[6-8]。作为覆铜板（copper clad laminate，CCL）领域通用基体树脂之一，EP的易燃特性易导致元器件损坏，无法满足高频高速CCL的发展需求[9-10]。因此，提升EP的阻燃性能成为CCL领域的重要研究方向之一。
卤系阻燃剂具有阻燃效率高、成本低等优势，是EP阻燃改性研究中应用最为广泛的一类阻燃剂，但因其具有环境毒性和生物富集性等问题，已被欧盟限制使用[11-12]。磷系阻燃剂因其无卤、低毒、低烟、高效等特性，成为了卤系阻燃剂最主要的替代品[13-15]。磷系阻燃剂可分为添加型含磷阻燃剂和反应型含磷阻燃剂。添加型含磷阻燃剂通过与EP机械共混的方式，赋予EP良好的阻燃性，此种方法工艺简单、阻燃剂可选择性广，但存在着阻燃剂与基体相容性差、易导致EP玻璃化转变温度（Tg）降低等问题[16-17]。反应型含磷阻燃剂则能够在EP的固化过程中进行化学反应，通过增大阻燃链段分子量或共价结合的方式实现阻燃剂与基体的良好结合。该种方式具有稳定性好、阻燃作用持久等优势[18-19]。但传统反应型含磷酚醛或含磷环氧在固化过程中会产生大量易吸水的强极性羟基，导致所制备覆铜板的介电常数（Dk）和介质损耗因数（Df）增大，进而影响高频高速条件下的信号传输。因此，要满足高频高速CCL的使用要求，提升EP的介电性能同样至关重要[21-22]。
但目前对于覆铜板用EP的研究大多聚焦于介电性能和阻燃性能单方面的改善，对其阻燃与介电综合性能的研究较为匮乏。而在高频高速信息化时代的大背景下，具备优异综合性能的CCL是未来印制电路板行业发展的重点。
为同时优化EP介电性能与阻燃性能，本文首先以10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物（DOPO-HQ）和4-氯甲基苯乙烯（VBC）作为原料，合成一种低介质损耗反应型含磷阻燃剂DOPVB，然后将EP与DOPVB复配制备不同磷含量的EP/DOPVB复合材料，研究磷含量对复合材料阻燃、热学、介电等性能的影响。
1 实验
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1.1 实验原料
10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物（DOPO-HQ），工业级，江阴市涵丰科技有限公司；4-氯甲基苯乙烯（VBC），分析纯，山东星顺新材料有限公司；碳酸钾（K2CO3），分析纯，上海麦克林生化科技有限公司；二甲基亚砜（DMSO）、甲醇、丁酮，均为分析纯，成都科隆化学品有限公司；甲苯，化学纯，国药集团化学试剂有限公司；环氧树脂（D128，环氧基含量为186 g/mol）、活性酯固化剂（DFE618，酯基官能团含量为228 g/mol），均为工业级，四川东材科技集团股份有限公司。
1.2 实验步骤
1.2.1 DOPVB阻燃剂单体的合成
将一定比例的K2CO3、DMSO、DOPO-HQ加入到配备机械搅拌的500 mL四颈烧瓶中，通入N2并升温至65℃反应1 h。然后使用冰水降温至15℃开始滴加VBC，滴加时间为30 min，滴加结束后升温至60℃反应6 h，反应式如图1所示。反应结束后趁热过滤，滤液在常温下析出浅黄色粗品，使用蒸馏水洗涤粗品至水相为中性（pH=7），再用甲醇将固体洗涤至白色。最后用甲苯进行重结晶，得到DOPVB单体，产物为白色晶体。
1.2.2 EP/DOPVB树脂固化物的制备
在烧杯中依次加入一定量的环氧树脂、活性酯和DOPVB单体，机械搅拌4 h，然后装入铝箔纸盒中在140℃下预固化15 min，使其在171℃下的凝胶时间为100～120 s。最后在真空度为22 kPa的热压机中热压成型制备成环氧树脂固化物，压合条件为165℃/60 min+200℃/90 min。
1.2.3 EP/DOPVB复合材料的制备
（1）胶液的制备：按表1配方，将环氧树脂、活性酯、DOPVB和丁酮混合搅拌均匀配成预浸胶液。
（2）半固化片制备：将玻纤布浸入配好的胶液并均匀上胶，上胶量为35%。在171℃的鼓风干燥箱中烘烤5～7 min，制得半固化片。半固化片在171℃下的凝胶时间为120～130 s。
（3）板材制备：将20张上述半固化片叠配，上、下各放置1张铜箔，置于真空度为22 kPa的热压机中压制成层压板。压合条件为165℃/60 min+200℃/90 min。
1.3 测试与表征
（1）液相色谱分析（HPLC）：采用日本SHIMADZU公司LC 1260Ⅱ型高效液相色谱仪进行测试。
（2）红外光谱分析（FTIR）：采用美国PerkinElmer公司RX-1型傅里叶变换红外光谱仪进行测试，采用KBr压片法进行制样，扫描波数范围为500～4 000 cm-1。
（3）核磁波谱分析（NMR）：采用德国布鲁克科技有限公司FX201502型超导核磁共振波谱仪进行测试，以氘代二甲基亚砜为溶剂。
（4）差示扫描量热分析（DSC）：采用德国耐驰公司DSC200F3型差示扫描量热仪进行测试，氮气气氛，升温速率为10℃/min，温度范围为50～350℃。
（5）热失重分析（TGA）：采用德国耐驰公司TG209F3型热失重分析仪进行分析，氮气气氛，升温速率为10℃/min，温度范围为50～600℃。
（6）垂直燃烧（UL 94）测试：使用昆山阳屹测试仪器有限公司5402型水平-垂直燃烧试验机，参照ASTM D3801-2019进行测试。
（7）极限氧指数（LOI）测试：使用英国Stanton Redcroft公司31D-38型氧指数测定仪，参照GB/T 2406.2—2009进行测试。
（8）介电性能测试：采用美国是德科技公司P9373A型网络分析仪和波兰QWED公司SPDR夹具进行测试，频率为10 GHz。
2 结果与讨论
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2.1 DOPVB的结构表征与热性能分析
2.1.1 液相分析
图2为DOPO-HQ和DOPVB的液相色谱图，对反应原料DOPO-HQ与产物DOPVB单体的出峰情况进行对比分析。从图2可以看出，原料DOPO-HQ出峰时间位于3.44 min处，且其峰面积占据了总峰面积的98.87%；产物DOPVB的出峰时间延迟至5.76 min处，其峰面积为99.80%，这一数据不仅证实了DOPO-HQ向DOPVB的有效转化，还展现了产物DOPVB较高的纯度。
2.1.2 红外分析
采用红外光谱对原料DOPO-HQ、VBC以及产物DOPVB的结构进行表征，结果如图3所示。从图3可以看出，DOPVB位于3 415 cm-1处的-OH特征峰消失，1 231 cm-1和1 025 cm-1处出现了Ph-O-C特征吸收峰，表明DOPO-HQ的羟基与VBC的苄氯发生取代反应，形成了新的醚键。此外，DOPVB的FTIR图保留了来自于VBC中1 627 cm-1处的C=C特征吸收峰以及DOPO-HQ中1 278 cm-1处的P=O和1 581 cm-1处的P-Ph特征吸收峰，进一步说明反应成功进行。
2.1.3 核磁分析
DOPVB的1H-NMR谱图如图4所示。由图4可知，化学位移2.50处为DMSO的溶剂峰，3.33处为H2O的溶剂峰。5.08～5.28（c,d）和5.73～5.87（e,f）处为末端双键碳原子上的质子峰。4.76（a）处单峰和6.67～6.70（b）处双重峰对应的是亚甲氧基氢的质子峰，其中双重峰是由于自旋耦合裂分形成的。6.62～8.18之间的多重峰（除6.67～6.70处的双重峰外）对应DOPVB中苯环氢的质子峰。核磁表征的合成产物结构与理论产物结构相符，结合FTIR结果，可以确定本文已经成功合成目标产物DOPVB。
2.1.4 热学性能分析
阻燃剂DOPVB的热失重（TG）和热失重速率（DTG）曲线如图5所示。从图5可以看出，DOPVB在温度低于300℃时相对稳定，未出现明显热分解。随着温度逐渐升高，DOPVB在346.6℃时质量损失达到5%，在440.0℃时热分解速率最大，在600℃时残炭率为33.11%，以上表明DOPVB具有良好的热稳定性能。
2.2 产物合成条件优化
2.2.1 原料配比对产物产率的影响
保持反应温度、反应时间及K2CO3的用量不变，当DOPO-HQ和VBC物质的量之比分别为1∶2.0、1∶2.1、1∶2.2、1∶2.3、1∶2.4时，产物产率分别为64.10%、67.05%、72.33%、72.56%、72.85%。由此可知，随着VBC含量的增加，产物产率呈现增长趋势，从DOPO-HQ与VBC物质的量之比为1∶2.2开始，产率趋于稳定。
2.2.2 K2CO3用量对产物产率的影响
保持其他合成条件不变，反应物DOPO-HQ与VBC物质的量之比为1∶2.2，当DOPO-HQ与K2CO3物质的量之比分别为1∶2.0、1∶2.5、1∶3.0、1∶3.5、1∶4.0时，产物产率分别为65.68%、72.33%、74.57%、75.32%、75.91%，由此可知，随着K2CO3含量增加，产物产率逐渐增大。
2.2.3 反应时间对产物产率的影响
保持其他合成条件不变，反应物DOPO-HQ与VBC物质的量之比为1∶2.2，DOPO-HQ与K2CO3物质的量之比为1∶3.0，当反应时间分别为4、5、6、7、8 h时，产物产率分别为68.52%、73.33%、74.55%、72.56%、72.43%，由此可知，随着反应时间增加，产物产率先增大后减小。
综上，从节约资源、绿色环保的角度思考，合成DOPVB的最优反应条件为：反应物DOPO-HQ与VBC物质的量之比为1∶2.2，DOPO-HQ与K2CO3物质的量之比为1∶3.0，反应时间为6 h，该条件下产率为74.55%。
2.3 EP/DOPVB复合材料的燃烧性能分析
表2为EP/DOPVB复合材料的燃烧性能测试数据。
从表2可以看出，纯EP无法通过UL 94测试，LOI值仅为30.0%。随着EP/DOPVB复合材料中磷含量的增加，其LOI值显著提高，当磷含量为1.5%时，EP/DOPVB复合材料的LOI值达到66.6%，比纯EP提升了122%。此外，磷含量的增加使得复合材料在UL 94测试中展现出显著的提升效果，当磷含量达到2.0%和2.5%时，样品均达到了V-0级等级。因此，在制备此类复合材料时，可以通过控制DOPVB的添加量，确保达到理想的阻燃效果。
2.4 EP/DOPVB固化物的热性能分析
为了研究不同含量DOPVB对EP热性能的影响，在氮气气氛下对EP/DOPVB固化物进行热重和差示扫描量热分析测试。图6为纯EP和EP/DOPVB固化物的TG和DTG曲线，表3为详细的热分析数据。
由表3可知，EP/DOPVB固化物的玻璃化转变温度（Tg）随着磷含量的增加而明显升高，EP/DOPVB-2.5的Tg由纯EP的89.8℃升高到130.4℃，提高了45.21%。在EP/DOPVB结构中，DOPVB与环氧树脂固化分子链相互交织，形成了致密的互穿交联网络结构。这种结构的变化限制了聚合物链段的自由运动，从而有效提高了固化物的耐热性。
纯EP失重5%时对应的温度（T5%）为340.7℃，最大热分解速率（Dmax）为1.58%/min，在600℃时的残炭率为20.34%。随着DOPVB的加入，EP/DOPVB固化物的T5%和残炭率明显提升，同时Dmax有所下降，表明DOPVB的加入对EP的热稳定性有显著的提升效果。其中，残炭率的提升归因于DOPVB在分解过程中产生磷酸及偏磷酸，然后在脱水时促进了残炭的形成；同时DOPVB热解过程中产生了含磷的自由基，抑制了EP分子链的断链反应。当EP/DOPVB固化物中磷含量为2.5%时，Dmax由纯EP的1.58%/min降低至0.76%/min。此外，磷元素的促进成炭作用，使固化物的Tmax从纯EP的411.0℃降低至403.0℃。
2.5 EP/DOPVB固化物的介电性能分析
电气材料的介电常数（Dk）和介质损耗因数（Df）对于其实际应用有着十分重要的意义，两者数值越低，信号传播速度越快，信号损失越少。表4为纯EP和不同磷含量EP/DOPVB固化物的介电常数和介质损耗因数。
由表4可知，在10 GHz的频率下，相比纯EP，EP/DOPVB固化物的Dk和Df均有所降低，并且随着DOPVB含量的增加，二者降低趋势越明显。其中，EP/DOPVB-2.5固化物的Dk为2.98，相较于纯EP降低了21.99%；Df为0.005 03，相较于纯EP降低了72.16%，表明DOPVB阻燃剂能够显著降低树脂固化物的介电常数和介质损耗因数。
3 结论
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（1）以10-(2,5-二羟基苯基)-10-氢-9-氧杂-10-磷杂菲-10-氧化物与4-氯甲基苯乙烯为反应原料成功合成一种低介质损耗反应型含磷阻燃剂DOPVB，最佳合成条件为：反应物DOPO-HQ、VBC与K2CO3物质的量之比为1∶2.2∶3.0，反应时间为6 h，此时产率为74.55%。
（2）DOPVB阻燃剂能够显著降低EP固化物的介电常数和介质损耗因数，其中EP/DOPVB-2.5固化物在10 GHz下的Dk和Df分别为2.98和0.005 03，相较于纯EP分别降低了21.99%和72.16%。
（3）在EP/DOPVB复合材料中，DOPVB阻燃剂的加入能降低其最大热解速率，并具有促进成炭作用。当磷含量为2.0%时，复合材料可达到V-0等级，且LOI为65.8%。
（4）EP/DOPVB固化物的Tg随着磷含量的增加而明显升高，其中EP/DOPVB-2.5的Tg升高至130.4℃，较纯EP提高了45.21%。
基金
收起
  • 四川省科技成果转移转化示范项目(2023ZHCG0048)
  • 四川省省级工业发展资金绿色低碳优势产业创新任务揭榜攻关项目(2022JB202310)
  • 中央引导地方科技发展项目(2022ZYDF031)
文献
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2025年第58卷第5期
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doi: 10.16790/j.cnki.1009-9239.im.2025.05.006
  • 接收时间：2024-07-10
  • 首发时间：2025-12-04
  • 出版时间：2025-05-20
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  • 收稿日期：2024-07-10
  • 修回日期：2024-08-21
基金
四川省科技成果转移转化示范项目(2023ZHCG0048)
四川省省级工业发展资金绿色低碳优势产业创新任务揭榜攻关项目(2022JB202310)
中央引导地方科技发展项目(2022ZYDF031)
作者信息
    1.西南科技大学 材料与化学学院，四川 绵阳 621010
    2.四川东材科技集团股份有限公司，四川 绵阳 621024

通讯作者:

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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https://castjournals.cast.org.cn/joweb/jycl/CN/10.16790/j.cnki.1009-9239.im.2025.05.006
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2种不同金属材料的力学参数
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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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