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Article(id=1242756977907052614, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1242756974576775191, articleNumber=null, orderNo=null, doi=10.16790/j.cnki.1009-9239.im.2021.11.012, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1618329600000, receivedDateStr=2021-04-14, revisedDate=1620230400000, revisedDateStr=2021-05-06, acceptedDate=null, acceptedDateStr=null, onlineDate=1774225952781, onlineDateStr=2026-03-23, pubDate=1637510400000, pubDateStr=2021-11-22, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1774225952781, onlineIssueDateStr=2026-03-23, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1774225952781, creator=13701087609, updateTime=1774225952781, updator=13701087609, issue=Issue{id=1242756974576775191, tenantId=1146029695717560320, journalId=1149653034449285133, year='2021', volume='54', issue='11', pageStart='1', pageEnd='139', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1774225952044, creator=13701087609, updateTime=1774226047274, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1242757374059066044, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1242756974576775191, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1242757374059066045, tenantId=1146029695717560320, journalId=1149653034449285133, issueId=1242756974576775191, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=88, endPage=93, ext={EN=ArticleExt(id=1242756979882569830, articleId=1242756977907052614, tenantId=1146029695717560320, journalId=1149653034449285133, language=EN, title=Preparation and Characterization of Fluoro-containing Diamine Monomers for Low-dielectric Poly(imide-benzoxazole)s, columnId=1198664996516360309, journalTitle=Insulating Materials, columnName=Polyimide Film Special Issue, runingTitle=null, highlight=null, articleAbstract=

According to the application requirements of high-temperature resistant polymers with low dielectric constant (low-Dk) and low dielectric loss factor (low-Df) for the development of high frequency communication technology, two key diamine monomers for fluoro-containing poly(imide-benzoxazole)s (PIBO), including 2,2-bis[3-(4-aminobenzamide)-4-hydroxylphenyl] hexafluoropropane (p6FAHP) and 2,2-bis[3-(3-aminobenzamide)-4-hydroxyphenyl] hexafluoropropane (m6FAHP) were synthesized. The dinitro compounds containing bis (o-hydroxy substituted benzamide) groups in molecular structure were first prepared by the low temperature reactions of the nitro-substituted benzoyl chloride and 2,2-bis(3-amino-4- hydroxyphenyl)hexafluoro-propane (6FAP) in polar aprotic solvent. Then the diamine monomers were obtained by the reduction of hydrogen under the catalysis of Pd/C. The melting points of the diamines were measured by DSC. The chemical structures of the diamines were characterized by ATR-FTIR, NMR, and elemental analysis (EA). The results show that the aromatic diamine monomers with expected structures are prepared successfully.

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针对高频通讯技术的发展对于具有低介电常数（low-Dk）以及低介质损耗因数（low-Df）型耐高温聚合物介质材料的应用需求，开展了含氟型聚（酰亚胺-苯并噁唑）（PIBO）用关键芳香族二胺单体，包括2,2-双［3-（4-胺基苯甲酰胺）-4-羟基苯基］六氟丙烷（p6FAHP）与2,2-双［3-（3-胺基苯甲酰胺）-4-羟基苯基］六氟丙烷（m6FAHP）的合成研究。采用硝基取代苯甲酰氯与2,2-双［（3-胺基-4-羟基）苯基］六氟丙烷（6FAP）在极性非质子性溶剂中低温反应，首先合成了分子结构中含有双（邻羟基取代苯甲酰胺）基团的二硝基化合物，然后在Pd/C催化下采用氢气还原得到了二胺基化合物。采用差示扫描量热分析（DSC）手段测试两种二胺单体的熔点，并采用衰减全反射傅里叶红外光谱（ATR-FTIR）、核磁（NMR）以及元素分析（EA）等手段表征二胺单体的化学结构。结果成功制得了预期结构的芳香族二胺单体。

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刘金刚（1973-），男（汉族），内蒙古赤峰人，教授，博士，主要从事电工与电子绝缘用聚合物材料的基础与应用研究。
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职欣心（1996-），女（汉族），新疆喀什人，博士生，主要从事高性能聚酰亚胺液晶取向膜材料的研究。

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职欣心（1996-），女（汉族），新疆喀什人，博士生，主要从事高性能聚酰亚胺液晶取向膜材料的研究。

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职欣心（1996-），女（汉族），新疆喀什人，博士生，主要从事高性能聚酰亚胺液晶取向膜材料的研究。

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项目MPIMPBO
耐热性能●●
介电性能□●
溶液加工性能●△
吸湿率△●
光敏化特性●●
改性窗口●×
成本△×
), ArticleFig(id=1245100056295096798, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1242756977907052614, language=CN, label=表1, caption=

改性PI与改性PBO的对比

, figureFileSmall=null, figureFileBig=null, tableContent=
项目MPIMPBO
耐热性能●●
介电性能□●
溶液加工性能●△
吸湿率△●
光敏化特性●●
改性窗口●×
成本△×
), ArticleFig(id=1245100056383177186, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1242756977907052614, language=EN, label=Tab.2, caption=Elemental analysis results of diamine monomers, figureFileSmall=null, figureFileBig=null, tableContent=
二胺单体项目元素含量/%
CHN
p6FAHP（C29H22F6N4O4）计算值57.623.679.27
实测值57.333.729.16
m6FAHP（C29H22F6N4O4）计算值57.623.679.27
实测值57.413.759.23
), ArticleFig(id=1245100056467063268, tenantId=1146029695717560320, journalId=1149653034449285133, articleId=1242756977907052614, language=CN, label=表2, caption=

二胺单体的元素分析结果

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二胺单体项目元素含量/%
CHN
p6FAHP（C29H22F6N4O4）计算值57.623.679.27
实测值57.333.729.16
m6FAHP（C29H22F6N4O4）计算值57.623.679.27
实测值57.413.759.23
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低介电聚（酰亚胺-苯并噁唑）用含氟二胺单体的制备与表征
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职欣心 1 , 李忠 2 , 沈登雄 2 , 杨洋 3 , 皇甫梦鸽 1 , 吴琳 1 , 张燕 1 , 刘金刚 1
绝缘材料 | 聚酰亚胺薄膜专题 2021,54(11): 88-93
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绝缘材料 | 聚酰亚胺薄膜专题 2021, 54(11): 88-93
低介电聚（酰亚胺-苯并噁唑）用含氟二胺单体的制备与表征
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职欣心1, 李忠2, 沈登雄2, 杨洋3, 皇甫梦鸽1, 吴琳1, 张燕1, 刘金刚1
作者信息
  • 1中国地质大学（北京）材料科学与工程学院，北京 100083
  • 2航天材料及工艺研究所，北京 100076
  • 3中国商飞复合材料中心，上海 201324

    • 职欣心（1996-），女（汉族），新疆喀什人，博士生，主要从事高性能聚酰亚胺液晶取向膜材料的研究。

通讯作者:

刘金刚（1973-），男（汉族），内蒙古赤峰人，教授，博士，主要从事电工与电子绝缘用聚合物材料的基础与应用研究。
Preparation and Characterization of Fluoro-containing Diamine Monomers for Low-dielectric Poly(imide-benzoxazole)s
Xinxin ZHI1, Zhong LI2, Dengxiong SHEN2, Yang YANG3, Mengge HUANGFU1, Lin WU1, Yan ZHANG1, Jingang LIU1
Affiliations
  • 1School of Materials Science and Technology, China University of Geosciences, Beijing 100083, China
  • 2Aerospace Research Institute of Materials& Processing Technology, Beijing 100076, China
  • 3China Composites Center of Commercial Aircraft Corporation of China, Ltd., Shanghai 201324, China
出版时间: 2021-11-22 doi: 10.16790/j.cnki.1009-9239.im.2021.11.012
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摘要
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针对高频通讯技术的发展对于具有低介电常数（low-Dk）以及低介质损耗因数（low-Df）型耐高温聚合物介质材料的应用需求，开展了含氟型聚（酰亚胺-苯并噁唑）（PIBO）用关键芳香族二胺单体，包括2,2-双［3-（4-胺基苯甲酰胺）-4-羟基苯基］六氟丙烷（p6FAHP）与2,2-双［3-（3-胺基苯甲酰胺）-4-羟基苯基］六氟丙烷（m6FAHP）的合成研究。采用硝基取代苯甲酰氯与2,2-双［（3-胺基-4-羟基）苯基］六氟丙烷（6FAP）在极性非质子性溶剂中低温反应，首先合成了分子结构中含有双（邻羟基取代苯甲酰胺）基团的二硝基化合物，然后在Pd/C催化下采用氢气还原得到了二胺基化合物。采用差示扫描量热分析（DSC）手段测试两种二胺单体的熔点，并采用衰减全反射傅里叶红外光谱（ATR-FTIR）、核磁（NMR）以及元素分析（EA）等手段表征二胺单体的化学结构。结果成功制得了预期结构的芳香族二胺单体。

耐高温聚合物  /  低介电常数  /  聚（酰亚胺-苯并噁唑）  /  二胺单体

According to the application requirements of high-temperature resistant polymers with low dielectric constant (low-Dk) and low dielectric loss factor (low-Df) for the development of high frequency communication technology, two key diamine monomers for fluoro-containing poly(imide-benzoxazole)s (PIBO), including 2,2-bis[3-(4-aminobenzamide)-4-hydroxylphenyl] hexafluoropropane (p6FAHP) and 2,2-bis[3-(3-aminobenzamide)-4-hydroxyphenyl] hexafluoropropane (m6FAHP) were synthesized. The dinitro compounds containing bis (o-hydroxy substituted benzamide) groups in molecular structure were first prepared by the low temperature reactions of the nitro-substituted benzoyl chloride and 2,2-bis(3-amino-4- hydroxyphenyl)hexafluoro-propane (6FAP) in polar aprotic solvent. Then the diamine monomers were obtained by the reduction of hydrogen under the catalysis of Pd/C. The melting points of the diamines were measured by DSC. The chemical structures of the diamines were characterized by ATR-FTIR, NMR, and elemental analysis (EA). The results show that the aromatic diamine monomers with expected structures are prepared successfully.

high-temperature resistant polymers  /  low dielectric constant  /  poly(imide-benzoxazole)  /  diamine monomer
职欣心, 李忠, 沈登雄, 杨洋, 皇甫梦鸽, 吴琳, 张燕, 刘金刚. 低介电聚（酰亚胺-苯并噁唑）用含氟二胺单体的制备与表征. 绝缘材料, 2021 , 54 (11) : 88 -93 . DOI: 10.16790/j.cnki.1009-9239.im.2021.11.012
Xinxin ZHI, Zhong LI, Dengxiong SHEN, Yang YANG, Mengge HUANGFU, Lin WU, Yan ZHANG, Jingang LIU. Preparation and Characterization of Fluoro-containing Diamine Monomers for Low-dielectric Poly(imide-benzoxazole)s[J]. Insulating Materials, 2021 , 54 (11) : 88 -93 . DOI: 10.16790/j.cnki.1009-9239.im.2021.11.012
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0 引言
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近年来，随着以第五代（5G）移动通讯技术为代表的先进信息技术领域的快速发展，对于具有优良综合性能电子信息材料的需求日益迫切[1]。5G等先进通讯技术的发展对相关材料提出了苛刻的性能需求，包括优异的耐热稳定性以适应电子器件高温制造以及高速运转所产生的热环境[2]；优异的介电性能以适应高频信号传输所带来的介质损耗等问题[3]；优异的光敏化特性以适应光电器件制图通孔等光刻工艺的需要[4]；以及尽可能宽的改性窗口和尽可能低的成本。此外，某些特定情况下还需要具有优异的溶液加工特性和低固化温度以适应某些温度敏感型光电器件的制造需求[5]。芳杂环高分子材料是满足上述需求的重要材料品种，并且在上述领域中的应用得到了越来越广泛的重视[6]。
聚酰亚胺（PI）与聚苯并噁唑（PBO）是目前电子信息领域中应用最为广泛的两类芳杂环高分子材料[7-8]。标准型PI与PBO材料最早被用于航空航天、武器制造、电工绝缘等领域用轻质、高强部件的制造中。PI与PBO薄膜与纤维材料已在上述领域应用了半个多世纪。近年来，随着电子信息产业的迅猛发展，PI与PBO材料的应用得到了进一步拓展[9]。但传统标准型PI与PBO材料应用于电子信息产业中仍存在着诸多性能上的不足，为此各种改性PI（modified PI，MPI）与改性PBO（modified PBO，MPBO）材料应运而生。目前常见的改性手段包括氟化、氢化、纳米改性等[10]。表1对比了MPI与MPBO的性能与应用特性。从表1可以看出，经过改性后，MPI与MPBO在耐热性能、光敏化特性等方面均可满足电子器件的应用需求，但在介电性能以及吸湿率这两项电子信息应用领域最为关注的性能方面，MPBO具有MPI无法比拟的优势。PI材料分子结构中固有的极性酰亚胺环使其介电常数（Dk）以及介质损耗因数（Df）偏高，尤其是在潮湿状态下更是如此[11]。但是MPI在溶液加工特性以及成本方面明显优于MPBO，这主要是由于可用于制备PBO的商业化单体种类十分有限，在很大程度上造成了MPBO改性窗口较窄，成本高昂。
鉴于MPI与MPBO在性能与应用特性方面各自具有独特的优势，近年来将MPI与MPBO进行复合改性的研究得到了广泛的重视[12-13]。制备的聚（酰亚胺-苯并噁唑）（PIBO）材料分子结构中同时含有酰亚胺环与苯并噁唑环，可在较大程度上降低PI的吸湿率、介电常数和介质损耗因数，同时可拓宽PBO的改性窗口以及降低成本[14]。目前文献中关于PIBO的应用研究多集中在气体分离膜[15-16]、高性能纤维[17]等领域，而在电子信息领域中的应用研究则相对较少[18-19]。关于PIBO的合成途径目前文献报道中主要包括如下3类：①采用含有预构筑有苯并噁唑环单元的二酐或二胺单体与常规单体聚合制备PIBO[20-21]；②首先采用常规二酐单体与含邻位取代羟基的二胺单体聚合制备聚（羟基-酰亚胺）（PHI），然后在450℃以上高温环境中脱除CO2，进而转化为PIBO[22]；③首先采用分子结构中含有邻羟基取代苯甲酰胺结构的二酐或二胺单体与常规单体聚合制备PHI，然后在300～350℃高温环境中脱除H2O，制得PIBO。例如，G L TULLOS等[23-24]在1999年首次报道了含邻位取代羟基的PI在500℃高温环境下脱除CO2转化为了PBO。WANG H等[25]于2014年报道了由含邻位取代羟基的PI转化为PBO的反应具有很强的薄膜厚度依存性。他们还报道了采用偏苯三酸酐酰氯与双（邻胺基苯酚）单体聚合首先制备聚（羟基-酰胺-酰胺酸）（PHAA），然后在200～300℃下热环化为PIBO，再进一步升温至300～400℃可完全转化为PBO[36]。SONG G等[27]报道了采用分子结构中含有预构筑苯并噁唑单元的芳香族二胺单体与常规芳香族二酐单体制备PIBO。然而目前文献中报道的几种制备PIBO的途径均存在一定的缺陷，如由含邻位取代羟基的PI脱除CO2制备PIBO往往需要高达450℃以上的高温环境；由含有预构筑苯并噁唑单元的单体制备PIBO受限于极其有限的商业化单体品种，而且改性窗口较窄。为此，近年来采用分子结构中含有邻羟基取代苯甲酰胺类单体制备PIBO的研究得到了广泛的重视。邻羟基取代苯甲酰胺单元可在相对较低温度下（≤350 ℃）转化为苯并噁唑环，而且可以通过-OH实现光敏化或其他改性，因此在电子信息领域用高性能聚合物材料中得到了广泛的重视。
本研究针对高性能PIBO研发的应用需求，对其合成用重要单体——含邻羟基取代苯甲酰胺类芳香族二胺的合成进行研究，包括2,2-双[3-(4-胺基苯甲酰胺)-4-羟基苯基]六氟丙烷（p6FAHP）与2,2-双[3-(3-胺基苯甲酰胺)-4-羟基苯基]六氟丙烷（m6FAHP），并采用各种测试手段对其结构进行表征。
1 实验
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1.1 主要原材料
对硝基苯甲酰氯（pNBC）、间硝基苯甲酰氯（mNBC）、2,2-双[(3-胺基-4-羟基)苯基]六氟丙烷（6FAP）、Pd/C（5%），分析纯，日本东京应化株式会社（TCI），直接使用。超干N-甲基吡咯烷酮（NMP）与超干吡啶，纯度≥99.5%，水分含量≤200 ×10-6，北京伊诺凯科技有限公司，直接使用。氢气，北京普莱克斯实用气体有限公司，直接使用。其他化学试剂，分析纯，国药集团化学试剂北京有限公司，直接使用。
1.2 合成步骤
以2,2-双[3-(4-胺基苯甲酰胺)-4-羟基苯基]六氟丙烷（p6FAHP）为例说明二胺单体的合成步骤。在一个配有机械搅拌、温度计、冷水浴以及滴液漏斗的三口瓶中加入6FAP、NMP以及吡啶，在5～10℃下搅拌反应至反应物全溶。滴加pNBC的NMP溶液，加快搅拌。滴加完毕后，于5～10℃下继续反应6 h。将反应液缓慢倒入去离子水中，浸泡过夜。将生成的沉淀过滤收集，用蒸馏水洗涤至中性，烘干。重结晶后得到浅黄色结晶2,2-双[3-(4-硝基苯甲酰胺)-4-羟基苯基]六氟丙烷（p6FNHP），收率为88.3%。
在一个配有机械搅拌、温度计以及氢气通入装置的高压釜中加入一定量的p6FNHP、5% Pd/C以及一定量的四氢呋喃，升温至60℃，通入氢气保压至1.0 MPa，反应5 h后降温。撤去压力，过滤除去Pd/C。滤液经旋转蒸发仪蒸除溶剂，得到p6FAHP白色粉末，收率为86.5%。熔点：298.4℃（DSC峰值温度）。红外光谱（cm-1）：3 439，3 364，3 144，1 639，1 605，1 537，1 508，1 422，1 381，1 321，1 254，1 190，1 146以及1 101。核磁氢谱（400 MHz，DMSO-d6，δ）：10.39（s，2H），9.25（s，2H），7.96（s，2H），7.70～7.67（d，4H），7.00～6.93（m，4H），6.62～6.59（d，4H）以及5.84（s，4H）. 核磁碳谱（400 MHz，DMSO-d6，δ）：166.1，153.0，149.4，129.9，128.3，127.1，126.8，126.0，124.6，123.7，123.6，121.5，120.5，116.5，113.3，64.2，64.0，63.8，63.6以及63.4。元素分析（%）：C29H22F6N4O4（Mw=604.50 g/mol）。理论值：C， 57.62%；H，3.67%；N，9.27%；实测值：C， 57.33%；H，3.72%； N，9.16%。
2,2-双[3-(3-胺基苯甲酰胺)-4-羟基苯基]六氟丙烷（m6FAHP）按照类似的工艺合成，除了将对硝基苯甲酰氯替换为间硝基苯甲酰氯。熔点：318.8℃（DSC峰值温度）。红外光谱（cm-1）：3 439，3 366，3 148，1 649，1 584，1 545，1 514，1 435，1 362，1 331，1 300，1 256，1 192，1 138以及1 097。核磁氢谱（400 MHz，DMSO-d6，δ）：10.44（s，2H），9.27（s，2H），8.07（s，2H），7.18～7.10（m，6H），7.07～7.02（m，4H），6.79～6.75（m，2H）以及5.35（s，4H）。核磁碳谱（400 MHz，DMSO-d6，δ）：166.5，149.4，135.4，129.6，128.3，127.1，126.6，126.0，124.4，123.7，123.4，121.4，117.7，116.0，115.0，113.1，64.2，64.0，63.8，63.6以及63.4。元素分析（%）：C29H22F6N4O4（Mw=604.50 g/mol）。理论值：C，57.62%；H，3.67%；N，9.27%；实测值：C，57.41%；H，3.75%；N，9.23%。
1.3 结构表征
熔点采用德国耐驰公司DSC 214型差示扫描量热分析仪（DSC）进行测试，升温速率为10℃/min，测试环境为氮气。单体的红外光谱采用日本岛津公司的Iraffinity-1S型傅里叶红外光谱仪测试，采用高灵敏度单次衰减全反射附件Quest，获得衰减全反射傅里叶变换红外（ATR-FTIR）光谱。核磁共振氢谱（1H-NMR）和碳谱（13C-NMR）采用日本电子株式会社（JEOL）AV 400型光谱仪测试，溶剂为氘代二甲基亚砜（DMSO-d6），四甲基硅烷（TMS）作为化学位移内标峰。元素分析采用美国Thermo Electron SPA公司Flash EA1112型微量分析仪测试。
2 结果与讨论
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p6FAHP以及m6FAHP二胺单体的合成路线如图1所示。对硝基苯甲酰氯（pNBC）或间硝基苯甲酰氯（mNBC）首先分别与6FAP在NMP溶剂中低温反应生成分子结构中含有双（邻羟基取代苯甲酰胺）基团的二硝基化合物。吡啶作为反应产生的HCl副产物的吸收剂，将HCl以吡啶盐酸盐的形式从反应中脱除，促进反应向正向进行。虽然酰氯基团（-COCl）与6FAP分子结构中的胺基（-NH2）与羟基（-OH）位点均有反应的可能，但与前者反应所需的热力学与动力学条件更低，因此只要控制反应温度，产生副产物的概率就会得到有效控制，二硝基化合物的收率可达到85%以上。将制得的二硝基化合物在Pd/C催化剂作用下，采用氢气进行还原可高产率（≥90%）地制得最终的二胺单体，两步反应的总收率约为76%。
图2给出了两种二胺单体的熔点测试谱图（DSC）。从图2可以看出，p6FAHP与m6FAHP单体的DSC峰值温度（熔点）分别为298.4℃与318.8℃，而且熔限较窄，表明合成的单体具有较高的纯度。
两种二胺单体的ATR-FTIR谱图如图3所示。从图3可以看出，两种二胺单体具有类似的红外谱图。胺基中N-H键的特征伸缩振动吸收峰可在3 439 cm-1以及3 366 cm-1处清晰地观察到。而羟基中O-H键的特征伸缩振动吸收峰则可在3 150 cm-1处检测到。另外，还可以清晰观察到酰胺键（Ph-CONH-Ph）中羰基（C=O）位于1 649 cm-1处的伸缩振动峰（仲酰胺，酰胺I带）以及N-H键位于1 545 cm-1处的伸缩振动峰（仲酰胺，酰胺II带）。此外，C-F键位于1 256 cm-1处以及C-O键（Ph-OH）位于1 138 cm-1处的伸缩振动峰也可以准确地加以指认，表明成功制备了预期结构的单体。
图4给出了两种二胺单体的核磁氢谱（1H-NMR）。从图4可以看出，虽然两种二胺单体在ATR-FTIR中表现出较为相近的吸收峰，但在1H-NMR谱图中则表现出较大的差异。相同之处在于，两种二胺单体中，-OH中H质子的吸收均出现在谱图的最低场（p6FAHP：δ=10.39；m6FAHP：δ=10.44），而-CONH-键中H质子的吸收均位于谱图的次低场位置（p6FAHP：δ=9.25；m6FAHP：δ=9.27）。位于强吸电子六氟异丙基邻位的H质子（H3）的吸收也出现在谱图中较低场的位置。两种二胺单体中，胺基 （-NH2）上H质子的吸收均出现在谱图的最高场（除了溶剂与溶剂中的水吸收峰）（p6FAHP：δ=5.84；m6FAHP：δ=5.35）。位于胺基邻位的H质子（H1）的吸收出现在谱图中次低场位置。以上情况均与理论预期的结果一致。
图5给出了两种二胺单体的核磁碳谱（13C-NMR）。由于两种二胺单体中所含C原子的个数相对较多，而且各种C原子的化学环境也较为复杂，为此借助DEPT-135谱（distortionless enhancement by polarization transfer，无畸变极化转移）进行了C的归属分析。p6FAHP与m6FAHP 两种二胺单体的13C-NMR及对应的DEPT-135谱图分别如图6与图7所示。
由图5以及图6可以看出，p6FAHP单体结构中共记录了13个吸收峰，这与其化学结构特征是一致的。-CONH-基团中强吸电子羰基上的C原子（Ce）的吸收出现在谱图的最低场（p6FAHP：δ=166.1；m6FAHP：δ=166.5），而脂肪六氟异丙基中季C（Cl）的吸收出现在谱图的最高场（除了溶剂吸收峰）（p6FAHP：δ=63.8；m6FAHP：δ=67.5）。p6FAHP分子结构中的芳香族季C（Ca、Ck）的吸收出现在谱图较低场的位置。六氟异丙基中位于-CF3结构中的C（Cm）受到-F的强烈作用而被裂分为四重峰（p6FAHP：δ=128.3、126.0、123.7、121.5；m6FAHP：δ=128.3、126.0、123.7、121.4），其耦合常数（JC-F）为30 Hz。这是-CF3结构的典型吸收特征。六氟异丙基中季C（Cl）受到邻位两个-CF3的影响，其吸收峰理论上会裂分为七重峰。但在图5(a)中只观察到明显的五重峰，这一方面可能是由于与-F的距离较远（JC-F=20 Hz），另一方面可能是由于仪器的测试灵敏度较低造成的。在图6(a)所示的DEPT-135谱图中，共有5个C原子出现了吸收，这与其分子结构特征是一致的。
由图5以及图7可以看出，m6FAHP的吸收表现出与p6FAHP一致的特征。同样可以观察到Cm与Cl吸收峰的裂分。不同之处在于m6FAHP在DEPT-135谱图（图7(a)）中，共有7个C原子出现了吸收，这主要是由于间位取代结构使得与-H相连的C原子的数目增加导致的。
表2给出了二胺单体的元素分析结果。从表2可以看出，合成的p6FAHP与m6FAHP分子结构中各种元素的含量与理论值基本一致，表明成功制备了预期结构的二胺单体，其纯度可以满足后续聚合的要求。
3 结论
收起
成功制备了两种分子结构中含有双（邻羟基取代苯甲酰胺）基团的芳香族二胺单体p6FAHP与m6FAHP，各种表征手段验证了所合成的二胺单体的化学结构。这类芳香族二胺单体有望兼顾PI与PBO的优良特性，可在保持聚合物固有的溶液加工特性以及良好光学与耐热性能的同时，赋予其低介电常数特性。
基金
收起
  • 深圳市科技计划项目(JSGG20210629144539012)
  • 山东省重点研发计划重大科技创新工程项目(2019JZZY020235)
  • 上海市自然科学基金项目(17ZR1411800)
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2021年第54卷第11期
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doi: 10.16790/j.cnki.1009-9239.im.2021.11.012
  • 接收时间：2021-04-14
  • 首发时间：2026-03-23
  • 出版时间：2021-11-22
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  • 收稿日期：2021-04-14
  • 修回日期：2021-05-06
基金
深圳市科技计划项目(JSGG20210629144539012)
山东省重点研发计划重大科技创新工程项目(2019JZZY020235)
上海市自然科学基金项目(17ZR1411800)
作者信息
    1中国地质大学（北京）材料科学与工程学院，北京 100083
    2航天材料及工艺研究所，北京 100076
    3中国商飞复合材料中心，上海 201324

通讯作者:

刘金刚（1973-），男（汉族），内蒙古赤峰人，教授，博士，主要从事电工与电子绝缘用聚合物材料的基础与应用研究。
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https://castjournals.cast.org.cn/joweb/jycl/CN/10.16790/j.cnki.1009-9239.im.2021.11.012
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2种不同金属材料的力学参数
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Number of
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Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
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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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