CN114230794A - 改性双马来酰亚胺预聚物及树脂组合物、应用 - Google Patents
改性双马来酰亚胺预聚物及树脂组合物、应用 Download PDFInfo
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- CN114230794A CN114230794A CN202111661546.8A CN202111661546A CN114230794A CN 114230794 A CN114230794 A CN 114230794A CN 202111661546 A CN202111661546 A CN 202111661546A CN 114230794 A CN114230794 A CN 114230794A
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- Prior art keywords
- bismaleimide
- diamine compound
- prepolymer
- resin
- modified
- Prior art date
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 title claims abstract description 116
- 239000011342 resin composition Substances 0.000 title claims abstract description 37
- -1 diamine compound Chemical class 0.000 claims abstract description 84
- 229920005989 resin Polymers 0.000 claims abstract description 73
- 239000011347 resin Substances 0.000 claims abstract description 73
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 57
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 49
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000003063 flame retardant Substances 0.000 claims description 24
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 17
- 239000002184 metal Substances 0.000 claims description 17
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- YBUPZEKLPLIZNR-UHFFFAOYSA-N C.C(C)C=1C=CC=C(C1N1C(C=CC1=O)=O)C.C(C)C=1C=CC=C(C1N1C(C=CC1=O)=O)C Chemical compound C.C(C)C=1C=CC=C(C1N1C(C=CC1=O)=O)C.C(C)C=1C=CC=C(C1N1C(C=CC1=O)=O)C YBUPZEKLPLIZNR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004593 Epoxy Substances 0.000 description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
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- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一种改性双马来酰亚胺预聚物及树脂组合物、应用，以二胺化合物在有机溶剂中改性双马来酰亚胺树脂得所述改性双马来酰亚胺预聚物；其中，所述二胺化合物包括含茚满结构二胺化合物。
Description
技术领域
本发明属于电子材料技术领域，关于一种改性双马来酰亚胺预聚物及树脂组合物、应用。
背景技术
随着技术的升级，汽车市场、智能手机等消费类电子市场对PCB(印制电路板)提出了新的需求，而2018年5G商用上市以后，对PCB基材的介电性能方面的要求更上一层台阶，高频高速覆铜层压板是5G时代不可或缺的电子基材之一。简单来说，即PCB的基板材料需要具备较低的介电常数和介电损耗正切，以减少高速传输时信号的延迟、失真和损耗，以及信号之间的干扰。因此，业界期望提供一种热固性树脂组合物，使用这种热固性树脂组合物制作的印制电路板基板在高速化、高频化的信号传输过程中能表现出充分低的低介电常数和低介电损耗正切(即介电常数和介电损耗正切越低越好)。
在现有的制备印制电路板的树脂组合物中，双马来酰亚胺是非常优秀的树脂之一，它是一种含有酰亚胺结构的热固性树脂，其固化后高的交联密度使其具有高玻璃化转变温度、优异的热稳定性及较高的刚性，为目前制作薄型基板的首选材料之一。然而，双马来酰亚胺单体存在熔点较高、溶解性较差、介电性能不高等不足，因而，限制了其在高频高速领域中的应用。
针对上述技术问题，目前已有烯丙基化合物或芳香二胺化合物改性双马来酰亚胺树脂为主的两种较成熟的技术路线，如Huntsman公司于上世纪推出的Kerimid系列树脂，西北工业大学梁国正教授团队开发的烯丙基化合物改性双马系列树脂，所制得的改性双马来酰亚胺树脂具有高韧性、优异的溶解性(可溶于丙酮/丁酮等有机溶剂)、高的玻璃化转变温度等优异性能。但是，改性双马来酰亚胺树脂在介电性能方面改善并不明显。
而，三菱瓦斯的双马来酰亚胺三嗪树脂(BT树脂)可以说是双马来酰亚胺和氰酸酯应用的典范，双马来酰亚胺—氰酸酯树脂(BT)是一种具有优异介电性能的理想基体材料，虽成功解决了双马来酰亚胺树脂应用的介电性能问题，且专利技术已公开，但其关键技术要点仍难以为国内技术人员所掌握。专利公开号WO2020217672A1的专利中公开了一种具有高耐热性和低介电常数和介质损耗的含茚满骨架的马来酰亚胺树脂，但是该树脂合成工艺复杂，价格昂贵，关键技术掌握在国外厂商。
因此，开发一种具有优异的介电性能的改性双马来酰亚胺树脂基树脂组合物、及使用其制作的半固化片及层压板，使其在兼具优异的耐热性、强度、高玻璃化转变温度的基础上，降低介电常数和介质损耗值，显然具有积极的现实意义。
发明内容
本发明的目的在于提供基于双马来酰亚胺树脂基的预聚物、树脂组合物及其在半固化片、层压板中的应用，使其维持优异的耐热性、强度、高玻璃化转变温度，以及，具有低介电常数和介质损耗值。
本发明的技术方案提供了一种改性双马来酰亚胺预聚物，以二胺化合物在有机溶剂中改性双马来酰亚胺树脂得所述改性双马来酰亚胺预聚物；其中，所述二胺化合物包括含茚满结构二胺化合物。
作为可选的技术方案，所述含茚满结构二胺化合物的结构式如式(1)所示：
其中，式(1)中，R2为氢或C1-C6烷基；R3为氢或C1-C6烷基；b为0或1-3整数；优选为，R2为甲基或者乙基。
作为可选的技术方案，所述二胺化合物为含茚满结构二胺化合物和分子结构不含茚满结构二胺化合物混合成的混合物。
作为可选的技术方案，所述双马来酰亚胺树脂与二胺化合物的重量比为100:30～30:100；其中，优选的，所述双马来酰亚胺树脂与二胺化合物的重量比为60:30～30:60。
作为可选的技术方案，以所述二胺化合物总重量100份计，含茚满结构二胺化合物为0.1～100wt％，其中，优选的，含茚满结构二胺化合物为10～60wt％。
作为可选的技术方案，所述双马来酰亚胺树脂的结构式为如式(2)所示：
其中，式(2)中，R1选自亚甲基、氧、
R2和R3分别选自氢、甲基或乙基；且R2和R3可以相同或不同。
作为可选的技术方案，所述双马来酰亚胺树脂为4,4’-二苯甲烷双马来酰亚胺、4,4’-二苯醚双马来酰亚胺、4,4’-二苯砜双马来酰亚胺及双(3-乙基-5-甲基-4-马来酰亚胺基苯)甲烷中的一种或一种以上的混合物。
本发明还提供一种使用如上述的改性双马来酰亚胺预聚物制备得到的树脂组合物，以固体重量计，所述树脂组合物包括：
(a)改性双马来酰亚胺预聚物：100重量份；
(b)热固性树脂：0～50重量份；
(c)阻燃剂：0～100重量份。
作为可选的技术方案，所述阻燃剂为5～50重量份。
本发明还提供根据上述树脂组合物的应用，应用于半固化片、层压板、金属箔层压板中。
本发明提供一种改性双马来酰亚胺预聚物及树脂组合物、应用，改性双马来酰亚胺预聚物通过使用含茚满结构二胺化合物改性双马来酰亚胺树脂制得，在改性双马来酰亚胺的预聚过程中，引入茚满结构结构至双马来酰亚胺树脂结构中，茚满结构结构使得双马来酰亚胺预聚物中的非极性官能基的占比增加，因此基于含茚满结构的双马来酰亚胺预聚物柔韧性显著增加，其在半固化片、层压板中应用表现出低的介电常数和介电损耗，以及，更高耐热性。
与现有技术相比，本发明改性双马来酰亚胺预聚物及树脂组合物、应用具有以下优点：
(1)本发明将含茚满结构二胺化合物与双马来酰亚胺树脂发生预聚反应，获得具有优异的溶解性和工艺操作性的改性双马酰亚胺树脂预聚物。
(2)本发明是通过预聚方法在双马来酰亚胺树脂中引入茚满结构，保持较好的双马来酰亚胺树脂的耐热性，同时改善了双马来酰亚胺树脂的介电性能。
(3)使用由本发明的改性双马来酰亚胺树脂预聚物的树脂组合物获得的层压板具有优良的耐热性和介电性能，并满足较好的综合性能。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，下面结合实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅用以解释本发明，并不用于限定本发明。
本发明的目的在于设计合成一种含茚满结构的改性双马来酰亚胺预聚物，以及使用其制备得到树脂组合物，再将树脂组合物应用至半固化片、层压板和金属箔层压板中。其中，含茚满结构的改性双马来酰亚胺预聚物为使用包括含茚满结构二胺化合物在有机溶剂中改性双马来酰亚胺树脂制得。即，利用含茚满结构二胺化合物改性双马来酰亚胺树脂，将茚满结构引入到双马来酰亚胺树脂中，可显著改善基于双马来酰亚胺树脂基形成的固化物的特性，使其具有低介电常数和介质损耗值，以及优异的耐热性、强度、高玻璃化转变温度。
本发明提供的改性双马来酰亚胺预聚物是以二胺化合物在有机溶剂中改性双马来酰亚胺树脂制得，其中，二胺化合物中含有含茚满结构二胺化合物。
具体的，将双马来酰亚胺树脂与含茚满结构二胺化合物溶解在有机溶剂中，在温度60～110℃下反应1～24小时；制得改性双马来酰亚胺预聚物。
其中，双马来酰亚胺树脂与二胺化合物的重量比为100：30～30：100；优选地，双马来酰亚胺树脂与二胺的重量比为60：30～30：60。
本实施例中，上述二胺化合物为含茚满结构二胺化合物和分子结构中不含茚满结构二胺化合物形成的混合物，以上述二胺化合物总重量计，含茚满结构二胺化合物为0.1-100wt％(重量百分比)；其中，优选的，含茚满结构二胺化合物为10～60wt％(重量百分比)。
上述技术方案中，二胺化合物采用分子结构中不含茚满结构二胺化合物和含茚满结构二胺化合物形成的混合物，可增加二胺化合物、双马来酰亚胺树脂在有机溶剂中的溶解性，使得加工工艺更易实施。另外，分子结构中不含茚满结构二胺化合物的成本较含茚满结构二胺化合物的成本低，以部分分子结构中不含茚满结构二胺化合物替换含茚满结构二胺化合物，在维持改性双马来酰亚胺预聚物在半固化片、层压板、金属箔层压板的应用中的低介电常数和介质损耗值、高耐热性的基础上，可显著降低制造成本。
上述技术方案中,所述分子结构中不含茚满结构二胺化合物为选自：4，4’－二氨基二苯基甲烷、4，4’－二氨基－3，3’－二甲基二苯基甲烷、4，4’－二氨基－3，3’－二乙基二苯基甲烷、4，4’－二氨基二苯醚、4，4’－二氨基二苯砜、3，3’－二氨基二苯砜、4，4’－二氨基二苯基酮、4，4’－二氨基联苯、3，3’－二甲基－4，4’－二氨基联苯、2，2’－二甲基－4，4’－二氨基联苯、3，3’－二羟基联苯胺、2，2－双(3－氨基－4－羟苯基)丙烷、3，3’－二甲基－5，5’－二乙基－4，4’－二氨基二苯基甲烷、2，2－双(4－氨基苯基)丙烷、2，2－双(4－(4－氨基苯氧基)苯基)丙烷、1，3－双(3－氨基苯氧基)苯、1，3－双(4－氨基苯氧基)苯、1，4－双(4－氨基苯氧基)苯、4，4’－双(4－氨基苯氧基)联苯、1，3－双(1－(4－(4－氨基苯氧基)苯基)－1－甲基乙基)苯、1，4－双(1－(4－(4－氨基苯氧基)苯基)－1－甲基乙基)苯、4，4’－[1，3－亚苯基双(1－甲基亚乙基)]双苯胺、4，4’－[1，4－亚苯基双(1－甲基亚乙基)]双苯胺、3，3’－[1，3－亚苯基双(1－甲基亚乙基)]双苯胺、双(4－(4－氨基苯氧基)苯基)砜、双(4－(3－氨基苯氧基)苯基)砜中至少一种。
上述技术方案中，所述有机溶剂选自丙酮、丁酮、甲苯、二甲苯、甲醇、乙醇、甲基异丁酮、环己酮、甲基乙基酮、N、N-二甲基甲酰胺、N、N-二甲基乙酰胺、乙二醇甲醚、丙二醇甲醚、甲氧基乙基乙酸酯、乙氧基乙基乙酸酯、丙氧基乙基乙酸酯、乙酸乙酯中的一种或几种。其中优选为丙酮、丁酮或二甲苯。
上述技术方案中，含茚满结构二胺化合物的结构式如式(1)所示：
其中，式(1)中，R2为氢或C1-C6烷基；R3为氢或C1-C6烷基；b为0或1-3整数；优选的，R2为甲基或者乙基。
上述技术方案中，双马来酰亚胺树脂的结构式为如式(2)所示：
其中，式(2)中，R1选自亚甲基、氧、
R2和R3分别选自氢、甲基或乙基；且R2和R3可以相同或不同。
优选的，双马来酰亚胺树脂为4,4’-二苯甲烷双马来酰亚胺、4,4’-二苯醚双马来酰亚胺、4,4’-二苯砜双马来酰亚胺及双(3-乙基-5-甲基-4-马来酰亚胺基苯)甲烷中的一种或一种以上的混合物。通常双马来酰亚胺树脂为购自：日本大和制，产品名：BMI-1000、BMI-1100、BMI-2000、BMI-2300、BMI-4000、BMI-5100，或者，购自：日本KI化成制，产品名：BMI、BMI-70、BMI-80等。
本发明还提供一种使用上述改性双马来酰亚胺预聚物制备得到的树脂组合物，以固体重量计，树脂组合物包括：
(a)改性双马来酰亚胺预聚物：100重量份；
(b)热固性树脂：0～50重量份；
(c)阻燃剂：0～100重量份。
其中，(b)热固性树脂为选自本领域中常用的树脂，例如环氧树脂、苯并噁嗪树脂、氰酸酯树脂、马来酰亚胺树脂(除上述改性马来酰亚胺之外的其他马来酰亚胺树脂)、聚苯醚树脂、酚醛树脂、聚丁二烯、聚戊二烯、聚苯乙烯、丁二烯-苯乙烯共聚物、苯乙烯-丁二烯-苯乙烯共聚物等。
上述树脂组合物中，阻燃剂优选为5～50重量份；其中，阻燃剂含量过大，影响树脂组合物的性能，过小则使最终的固化物无法满足对阻燃性能的要求。
阻燃剂可以是溴系阻燃剂、磷系阻燃剂、氮系阻燃剂、有机硅阻燃剂、有机金属盐阻燃剂、无机系阻燃剂等。
具体的，溴系阻燃剂可以是十溴二苯醚、十溴二苯乙烷、溴化苯乙烯或者四溴邻苯二甲酰胺。
磷系阻燃剂可以是无机磷、磷酸酯化合物、磷酸化合物、次磷酸化合物、氧化磷化合物、以及9,10-二氢-9氧杂-10-磷杂菲-10-氧化物(DOPO)、10-(2，5二羟基苯基)-9,10-二氢-9氧杂-10-磷杂菲-10-氧化物(DOPO-HQ)、
(m为1-5的整数)、
10-苯基-9,10-二氢-9-氧杂-10-磷菲-10-氧化物、三(2,6二甲基苯基)磷、磷腈、改性磷腈等有机含磷化合物。
氮系阻燃剂可以是三嗪化合物、氰尿酸化合物、异氰酸化合物、吩噻嗪等。有机硅阻燃剂可以是有机硅油、有机硅橡胶、有机硅树脂等。有机金属阻燃剂可以是二茂铁、乙酰丙酮金属络合物、有机金属羰基化合物等。无机阻燃剂可以是氢氧化铝、氢氧化镁、氧化铝、氧化钡等。
当然，阻燃剂的种类并不以此为限，可以理解的是，所添加的阻燃剂可以根据层压板的具体应用领域而选择，如，对卤素有要求的应用领域，优选非卤阻燃剂，如含磷或者含氮的阻燃剂，更优选为磷腈(如牌号SPB-100)、DOPO或DOPO-HQ、改性磷腈(如牌号BP-PZ、PP-PZ、SPCN-100、SPV-100和SPB-100L)、
优选地，阻燃剂选择高熔点含磷阻燃剂，如
上述技术方案中，树脂组合物中还可以包括填料；其中，以树脂组合物中各组分的总重量为100计，填料为10～70wt％(重量百分数)。
填料为有机填料或无机填料，其中，无机填料选自非金属氧化物、金属氮化物、非金属氮化物、无机水合物、无机盐、金属水合物或无机磷中的一种或者至少任意两种的混合物；所述有机填料选自聚四氟乙烯粉末、聚苯硫醚、聚醚砜粉末中的至少一种。
优选地，无机填料选自熔融二氧化硅、结晶型二氧化硅、球型二氧化硅、空心二氧化硅、氢氧化铝、氧化铝、滑石粉、氮化铝、氮化硼、碳化硅、硫酸钡、钛酸钡、钛酸锶、碳酸钙、硅酸钙、云母、玻璃纤维粉中的至少一种。
更优选地，填料为二氧化硅，具体地，为经表面处理的球形二氧化硅，其中，表面处理剂为硅烷偶联剂，如含环氧基、氨基、乙烯基、丙烯酸酯基或烯丙基的硅烷偶联剂。
填料的粒径中度值为0.3～15μm，例如0.5μm、1μm、2μm、5μm、8μm、10μm、11μm、12μm、13μm、14μm或15μm，以及上述数值之间的具体点值，限于篇幅以及处于简明的考虑，本发明不再穷尽列举所述范围包括的具体点值。
优选地，填料的粒径中度值为1～5μm。
根据最终产品的不同要求，树脂组合物还包括0～5份其他助剂，其他助剂包括偶联剂、分散剂、染料。
具体的，偶联剂为硅烷偶联剂，如环氧硅烷偶联剂或氨基硅烷偶联剂；分散剂为γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三甲氧基硅烷等具有氨基且具有水解性基团或羟基的氨基系硅烷化合物、3-丙烯酰氧基丙基三甲氧基硅烷等具有环氧基且具有水解性基团或羟基的环氧系硅烷化合物、γ-甲基丙烯酰氧基丙基三甲氧基硅烷等具有乙烯基且具有水解性基团或羟基的乙烯基系硅烷化合物、阳离子系硅烷偶联剂，分散剂可用BYK制的Disperbyk-110、111、118、180、161、2009、BYK-W996、W9010、W903(均为产品名)；染料为荧光染料和黑色染料，其中荧光染料为吡唑啉等，所述黑色染料为炭黑(液态或粉末状)、吡啶络合物、偶氮络合物、苯胺黑、黑滑石粉、钴铬铬金属氧化物、吖嗪、酞菁等。
本发明还提供根据上述的树脂组合物的应用，应用于半固化片、层压板、金属箔层压板中。
具体的，还提供一种半固化片，半固化片的制备工艺如下：
将上述树脂组合物用溶剂溶解，搅拌均匀，并熟化，制成树脂组合物胶液，将增强材料浸渍在树脂组合物胶液中，然后将浸渍后的增强材料在50-170℃环境下烘烤1-10min，干燥后即可得到半固化片。
其中，增强材料为天然纤维、有机合成纤维、有机织物或者无机织物；优选地，增强材料采用玻璃纤维布，玻璃纤维布中优选使用开纤布或扁平布。此外，在增强材料采用玻璃纤维布时，玻璃纤维布一般都需要进行化学处理，以改善树脂组合物与玻璃纤维布的界面之间结合。化学处理主要方法是偶联剂处理，其所用的偶联剂优选用环氧硅烷或者氨基硅烷等，以提供良好的耐水性和耐热性。
本发明还提供一种采用上述半固化片制备的层压板，其制备步骤如下：
在一张上述半固化片的单面或双面覆上金属箔，或者将至少2张上述的半固化片叠加后，在其单面或双面覆上金属箔，热压成形，即可得到金属箔层压板。
上述层压板的压制条件为：在0.2～2MPa压力和180～250℃温度下压制2～4小时。
半固化片的数量可根据需要的层压板的厚度来确定，可用一张或多张。所述金属箔，可以是铜箔，也可以是铝箔，其材质不限；所述金属箔的厚度也没有特别限制，如5μm、8μm、12μm、18μm、35μm或70μm均可。
含茚满结构二胺化合物改性双马来酰亚胺树脂制备改性双马来酰亚胺预聚物，具体实施方式如下：
合成例1
在500ml三口烧瓶中加入100g溶剂N,N-二甲基甲酰胺，将4,4’-二苯甲烷双马来酰亚胺(购自：西安双马新材料)与含茚满结构二胺化合物，按照重量份80g:20g依次于投入三口烧瓶中，在90℃的油浴条件下持续搅拌，待烧瓶中固体完全溶解后开始计时，持续搅拌1.5hr后，将所得产物进行蒸馏，得到固含量为65％的改性双马来酰亚胺树脂预聚物溶液A。
合成例2
在500ml三口烧瓶中加入120g溶剂N,N-二甲基乙酰胺，将4,4’-二苯甲烷双马来酰亚胺与含茚满结构二胺化合物和4,4'-二氨基二苯砜(DDS)，按照重量份100g:50g依次于投入三口烧瓶中，其中,二胺化合物为含茚满结构二胺化合物和4,4'-二氨基二苯砜(DDS)的混合物，其中，含茚满结构二胺化合物和4,4'-二氨基二苯砜(DDS)的重量比为10:50；然后，在90℃的油浴条件下持续搅拌，待烧瓶中固体完全溶解后开始计时，持续搅拌2hr后，将所得产物进行蒸馏，得到固含量为60％的改性双马来酰亚胺树脂预聚物溶液B。
比较例1
在500ml三口烧瓶中加入120g溶剂N,N-二甲基乙酰胺，将4,4’-二苯甲烷双马来酰亚胺与4,4'-二氨基二苯砜(DDS)，按照重量份100g:50g依次于投入三口烧瓶中，然后，在90℃的油浴条件下持续搅拌，待烧瓶中固体完全溶解后开始计时，持续搅拌4.5hr后，将所得产物进行蒸馏，得到固含量为60％的改性双马来酰亚胺树脂预聚物溶液C。
半固化片及覆铜板的制备，具体实施方式如下：
按照固体重量计，按照表1中的数据称取将上述双马来酰亚胺改性例中所制备的含茚满结构的二胺改性双马来酰亚胺树脂溶液A-C中添加环氧树脂、固化剂(双酚A型环氧树脂，购自：Dow)、无机填料(二氧化硅，购自：江苏联瑞)，阻燃剂(十溴二苯醚、购自：雅宝)、固化促进剂(2-甲基咪唑，购自：四国化成)，并通过溶剂调节胶液固含量至60％，将胶液涂覆于玻璃纤维布上，浸润片刻，至160℃鼓风干燥箱中，烘烤3～6min，制成半固化片。
将半固化片裁剪至一定尺寸，在上下各放置一张电解铜箔，叠配成一定叠构，送入真空压机中压合，程序为150℃/60min1200℃/120min，制得金属箔层压板(或者覆铜层压板)，具体性能检测如表2所示。
对上述所有实施例1-3和比较例1-2中制备的半固化片和覆铜层压板进行性能测试。测试方法为：
(1)玻璃化转变温度：采用动态热机械分析法(DMA)方法测试。
(2)浸锡耐热性：使用50×50mm的两面带铜样品，浸入288℃的焊锡中，记录样品分层起泡的时间。
(3)介电常数：按照IPC-TM-650 2.5.5.9使用平板法，测定1GHz下的介电常数。
(4)介质损耗角正切：按照IPC-TM-650 2.5.5.9使用平板法，测定1GHz下的介电损耗因子。
表1、树脂组合物中各组分及用量
| 组分 | 实施例1 | 实施例2 | 实施例3 | 比较例1 | 比较例2 |
| 改性双马来酰亚胺预聚物溶液A/g | 100 | 100 | |||
| 改性双马来酰亚胺预聚物溶液B/g | 100 | ||||
| 改性双马来酰亚胺预聚物溶液C/g | 100 | 100 | |||
| 环氧树脂/g | 20 | - | 20 | ||
| 双酚A型环氧树脂/g | 5 | - | 5 | ||
| 二氧化硅/g | 50 | 50 | 50 | 50 | 50 |
| 十溴二苯醚/g | - | - | 5 | - | 5 |
| 2-甲基咪唑/g | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
表2、实施例1-3以及比较例1-2中制得的金属箔层压板的检测性能
| 项目 | 实施例1 | 实施例2 | 实施例3 | 比较例1 | 比较例2 |
| 玻璃化转变温度(Tg)/℃ | 278 | 272 | 268 | 235 | 228 |
| 浸锡耐热性/min | ＞10 | ＞10 | ＞10 | ＞10 | 9 |
| 介电常数(Dk) | 2.61 | 2.68 | 2.74 | 3.21 | 3.52 |
| 介质损耗(Df) | 0.0061 | 0.0065 | 0.0070 | 0.012 | 0.015 |
表2中性能测试数据显示：在半固化片、金属箔层压板的应用中，使用茚满结构二胺化合物改性双马来酰亚胺树脂得到改性双马来酰亚胺预聚物(实施例1、2和3)在介电常数、介电损耗上明显低于使用普通芳香族二胺化合物改性双马来酰亚胺树脂得到改性双马来酰亚胺预聚物(比较例1和比较例2)；且，玻璃化转变温度更高，具有更高耐热性。
综上，本发明提供一种改性双马来酰亚胺预聚物及树脂组合物、应用，改性双马来酰亚胺预聚物通过使用含茚满结构二胺化合物改性双马来酰亚胺树脂制得，在改性双马来酰亚胺的预聚过程中，引入茚满结构至双马来酰亚胺树脂结构中，茚满结构使得双马来酰亚胺预聚物中的非极性官能基的占比增加，因此基于含茚满结构的双马来酰亚胺预聚物柔韧性显著增加，其在半固化片、层压板中应用表现出低的介电常数和介电损耗，以及，更高耐热性。
与现有技术相比，本发明改性双马来酰亚胺预聚物及树脂组合物、应用具有以下优点：
(1)本发明将含茚满结构二胺化合物与双马来酰亚胺树脂发生预聚反应，获得具有优异的溶解性和工艺操作性的改性双马酰亚胺树脂预聚物。
(2)本发明是通过预聚方法在双马来酰亚胺树脂中引入茚满结构，保持较好的双马来酰亚胺树脂的耐热性，同时改善了双马来酰亚胺树脂的介电性能。
(3)使用由本发明的改性双马来酰亚胺树脂预聚物的树脂组合物获得的层压板具有优良的耐热性和介电性能，并满足较好的综合性能。
本发明已由上述相关实施例加以描述，然而上述实施例仅为实施本发明的范例。此外，上面所描述的本发明不同实施方式中所涉及的技术特征只要彼此之间未构成冲突就可以相互结合。必需指出的是，本发明还可有其他多种实施例，在不背离本发明精神及其实质的情况下，熟悉本领域的技术人员可根据本发明作出各种相应的改变和变形，但这些相应的改变和变形都应属于本发明所附的权利要求的保护范围。
Claims (10)
1.一种改性双马来酰亚胺预聚物，其特征在于，
以二胺化合物在有机溶剂中改性双马来酰亚胺树脂得所述改性双马来酰亚胺预聚物；
其中，所述二胺化合物包括含茚满结构二胺化合物。
2.根据权利要求1所述的改性双马来酰亚胺预聚物，其特征在于，所述含茚满结构二胺化合物的结构式如式(1)所示：
其中，式(1)中，R2为氢或C1-C6烷基；R3为氢或C1-C6烷基；b为0或1-3整数。
3.根据权利要求2所述的改性双马来酰亚胺预聚物，其特征在于，R2为甲基或者乙基。
4.根据权利要求1所述的改性双马来酰亚胺预聚物，其特征在于，所述二胺化合物为含茚满结构二胺化合物和分子结构中不含茚满结构二胺化合物混合成的混合物。
5.根据权利要求1所述的改性双马来酰亚胺预聚物，其特征在于，所述双马来酰亚胺树脂与二胺化合物的重量比为100:30～30:100。
6.根据权利要求1所述的改性双马来酰亚胺预聚物，其特征在于，以所述二胺化合物总重量100份计，含茚满结构二胺化合物为0.1～100wt％。
7.根据权利要求1所述的改性双马来酰亚胺预聚物，其特征在于，所述双马来酰亚胺树脂的结构式为如式(2)所示：
其中，式(2)中，R1选自亚甲基、氧、
R2和R3分别选自氢、甲基或乙基；且R2和R3可以相同或不同。
8.根据权利要求7所述的改性双马来酰亚胺预聚物，其特征在于，所述双马来酰亚胺树脂为4,4’-二苯甲烷双马来酰亚胺、4,4’-二苯醚双马来酰亚胺、4,4’-二苯砜双马来酰亚胺及双(3-乙基-5-甲基-4-马来酰亚胺基苯)甲烷中的一种或一种以上的混合物。
9.一种使用权利要求1-8中任一项所述的改性双马来酰亚胺预聚物制备得到的树脂组合物，其特征在于，以固体重量计，所述树脂组合物包括：
(a)改性双马来酰亚胺预聚物：100重量份；
(b)热固性树脂：0～50重量份；
(c)阻燃剂：0～100重量份。
10.根据权利要求9所述的树脂组合物的应用，其特征在于，应用于半固化片、层压板、金属箔层压板中。
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