CN117327356A - 可固化的聚合物组合物 - Google Patents
可固化的聚合物组合物 Download PDFInfo
- Publication number
- CN117327356A CN117327356A CN202310788888.9A CN202310788888A CN117327356A CN 117327356 A CN117327356 A CN 117327356A CN 202310788888 A CN202310788888 A CN 202310788888A CN 117327356 A CN117327356 A CN 117327356A
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- China
- Prior art keywords
- polymer composition
- curable polymer
- copolymer
- diisopropenylbenzene
- curable
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 169
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- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 25
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- 238000003860 storage Methods 0.000 claims abstract description 8
- 230000009477 glass transition Effects 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
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- 238000012360 testing method Methods 0.000 claims description 7
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 claims description 4
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- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 claims description 2
- KEJYHYCHSAIBAP-UHFFFAOYSA-N 1,2-dicyclohexyl-3,4-bis(prop-1-en-2-yl)benzene Chemical compound C1CCCCC1C1=C(C(C)=C)C(C(=C)C)=CC=C1C1CCCCC1 KEJYHYCHSAIBAP-UHFFFAOYSA-N 0.000 claims description 2
- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 claims description 2
- GVLXIKYSWGGDLX-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)-2-(2-propylcyclopropyl)benzene Chemical compound CCCC1CC1C1=CC(C(C)=C)=CC=C1C(C)=C GVLXIKYSWGGDLX-UHFFFAOYSA-N 0.000 claims description 2
- ZENYUPUKNXGVDY-UHFFFAOYSA-N 1,4-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C(C)=C)C=C1 ZENYUPUKNXGVDY-UHFFFAOYSA-N 0.000 claims description 2
- BVUFUXGQLRJYDA-UHFFFAOYSA-N 1-(3-methylcyclopentyl)-3,5-bis(prop-1-en-2-yl)benzene Chemical compound C1C(C)CCC1C1=CC(C(C)=C)=CC(C(C)=C)=C1 BVUFUXGQLRJYDA-UHFFFAOYSA-N 0.000 claims description 2
- IYSVFZBXZVPIFA-UHFFFAOYSA-N 1-ethenyl-4-(4-ethenylphenyl)benzene Chemical group C1=CC(C=C)=CC=C1C1=CC=C(C=C)C=C1 IYSVFZBXZVPIFA-UHFFFAOYSA-N 0.000 claims description 2
- VCNONMCQKBPBCY-UHFFFAOYSA-N 1-ethyl-3,5-bis(prop-1-en-2-yl)benzene Chemical compound CCC1=CC(C(C)=C)=CC(C(C)=C)=C1 VCNONMCQKBPBCY-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- IRZJWDIVVZUDKM-UHFFFAOYSA-N 2-cyclopentyl-3-methyl-1,4-bis(prop-1-en-2-yl)-5-propylbenzene Chemical compound CC1=C(C(C)=C)C(CCC)=CC(C(C)=C)=C1C1CCCC1 IRZJWDIVVZUDKM-UHFFFAOYSA-N 0.000 claims description 2
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- UXWXHEVHZVXRQU-UHFFFAOYSA-N 4-(2-cyclobutylethyl)-1,2-bis(prop-1-en-2-yl)benzene Chemical compound C1=C(C(C)=C)C(C(=C)C)=CC=C1CCC1CCC1 UXWXHEVHZVXRQU-UHFFFAOYSA-N 0.000 claims description 2
- UEAFNORNMPYBAU-UHFFFAOYSA-N 4-methyl-1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=C(C)C=C1C(C)=C UEAFNORNMPYBAU-UHFFFAOYSA-N 0.000 claims description 2
- ZYWUIIGAFQRAGK-UHFFFAOYSA-N 5-hexyl-2-methyl-1,3-bis(prop-1-en-2-yl)benzene Chemical compound CCCCCCC1=CC(C(C)=C)=C(C)C(C(C)=C)=C1 ZYWUIIGAFQRAGK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 abstract description 15
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- 125000000524 functional group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000003107 substituted aryl group Chemical group 0.000 description 3
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 2
- GIUBHMDTOCBOPA-UHFFFAOYSA-N 3h-1,3-benzothiazole-2-thione;zinc Chemical compound [Zn].C1=CC=C2SC(S)=NC2=C1 GIUBHMDTOCBOPA-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 239000004697 Polyetherimide Substances 0.000 description 2
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- 229920002397 thermoplastic olefin Polymers 0.000 description 1
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- 150000003585 thioureas Chemical class 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
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- JYTZMGROHNUACI-UHFFFAOYSA-N tris(ethenyl)-methoxysilane Chemical compound CO[Si](C=C)(C=C)C=C JYTZMGROHNUACI-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
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Abstract
本公开涉及一种可固化的聚合物组合物,其包含(i)二异烯基芳烃(DIAEA)和二乙烯基芳烃(DVA)的共聚物,和(ii)至少一种抗焦烧剂。所述共聚物在25℃下在烃溶剂中小于4小时的溶解度为至少10wt%,玻璃化转变温度(Tg)为50‑300℃,凝胶含量为小于5wt%。所述可固化的聚合物组合物在大于140℃的温度下固化,以获得在烃溶剂中凝胶含量>90%的固化聚合物组合物,以及低的Dk和Df值。所述可固化的聚合物组合物在诸如加工、储存等步骤中不交联或具有最小的过早交联,且可用于覆铜层压应用中。
Description
技术领域
本公开涉及可固化的聚合物组合物、其制备方法和应用。
背景技术
电子工业对开发用于不同最终用途应用的紧凑电子设备感兴趣。这种小型化装置处理大容量信息,需要具有高频和高速信号传输。小型化装置的关键部件之一是具有单或多介电层/叠层的电路材料。用于制造基板的优选介电层的特征在于低介电常数(Dk)、低耗散因子(Df)、减小的热膨胀系数(CTE)等。
具有低Dk和Df的聚合物需要具有其它性能例如机械性能、在溶剂中的溶解性、流动性能等的平衡,以适合用于介电层应用。含有交联聚合物的组合物可有助于改善所需的性能。然而,组合物中的某些聚合物是非常活性的,且在运输时、在储存期间或在加工组合物时难以控制它们的活性。抗焦烧剂或自由基清除剂在本领域中是已知的,以控制组合物中聚合物的活性,特别是避免过早交联。然而,此类添加剂不能有效地减少/阻止聚合物的过早交联,或者对Dk和Df有负面影响。
因此,需要一种具有高固化速率,同时在标准加工条件下使过早交联最小化并提供改进的电性能例如低Dk和Df的可固化的聚合物组合物。
发明概述
在一个方面,本公开涉及一种可固化的组合物,其包含、基本上由或由以下物质组成:(i)二异烯基芳烃和二乙烯基芳烃的共聚物和(ii)0.001-10wt%的抗焦烧剂。所述共聚物具有下述特征:二异烯基芳烃与二乙烯基芳烃的摩尔比为1:15-15:1;在25℃下在烃溶剂中小于4小时的溶解度为至少10wt%,根据说明书中所述的溶解度试验测量;玻璃化转变温度(Tg)为50-300℃,根据ASTM D3418测量;和凝胶含量为小于5wt%,基于共聚物的总重量,根据说明书中所述的凝胶含量测试测量。基于可固化的聚合物组合物的总重量,抗焦烧剂选自苯乙烯、α-甲基苯乙烯单体、α-甲基苯乙烯二聚体、α-甲基苯乙烯低聚物、受阻酚类化合物、非受阻酚类化合物、苯并咪唑、及其混合物。在40℃下储存1天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物在25℃下通过Brookfield粘度计测量的溶液粘度比不含抗焦烧剂的聚合物组合物的溶液粘度低至少20%。
在第二方面,可固化的聚合物组合物具有10:1-1:10的二异烯基芳烃与二乙烯基芳烃的摩尔比。
在第三方面,所述共聚物在25℃下在烃溶剂中小于4小时的溶解度为10-75wt%。
在第四方面,所述共聚物的凝胶含量为0.05-5wt%。
发明详述
整个说明书中将使用以下术语:
“[A、B和C]中的至少一个(一种)”或“[A、B和C]中的任何一个(一种)”或“选自[A、B和C],及其组合”意味着其中的单个成员、其中的一个以上的成员或其中的成员的组合。例如,A、B和C中的至少一个(一种)包括例如仅有A、仅有B或仅有C,以及A和B、A和C、B和C,或A、B和C,或A、B和C的任何其他所有组合。
“焦烧”是指在聚合物/组合物的储存、加工、运输等过程中由于热或光的影响聚合物/组合物将经历过早交联和丧失加工能力的现象。过早交联是在正常加工条件下固化聚合物/组合物之前的交联。
“抗焦烧剂”是指一种添加剂,其通过与自由基反应使聚合物/组合物中在加工、运输、储存等过程中过早产生的自由基失活/终止。
“固化的”或“交联的”可互换使用,是指形成共价键,所述共价键将一个聚合物链与另一个聚合物链连接,或将同一聚合物链中的一个聚合的重复单元与另一个重复单元连接,从而改变材料的性能。
“分子量”或Mw是指聚合物嵌段或嵌段共聚物的聚苯乙烯当量分子量,以g/mol或kg/mol计。Mw可通过凝胶渗透色谱法(GPC)使用聚苯乙烯校准标准物测量,例如根据ASTM5296-19进行。GPC检测仪可为紫外或折射率检测仪或其组合。使用市售聚苯乙烯分子量标准物校准色谱仪。如此校准的使用GPC测量的聚合物的Mw是聚苯乙烯当量分子量或表观分子量。本文所表示的Mw是在GPC迹线的峰处测量的,通常称为聚苯乙烯当量“峰值分子量”,表示为Mp。
“基本上无(不含)凝胶”是指聚合物含有<10,或<8,或<5,或<3,或<2,或<1wt%的不溶于烃溶剂的固体物质,所述烃溶剂例如甲苯、环己烷、甲乙酮(MEK)、二甲苯等。
“凝胶含量”是指固化的聚合物组合物在甲苯中的不溶物含量占固化的聚合物组合物(在浸入烃溶剂之前)的百分比。在一些实施方案中,凝胶含量为>90wt%(甲苯可萃取物<10wt%),或>95wt%(甲苯可萃取物<5wt%),或>98wt%(甲苯可萃取物<2wt%)。
“凝胶含量测试”是指通过将重量为G1的固化的聚合物组合物样品在室温下置于20倍体积的甲苯中4小时的时间段来测量凝胶含量。然后过滤甲苯中的内容物以回收固化的聚合物组合物的固体部分,然后干燥以完全除去溶剂,并称重,得到不溶物含量G2。凝胶含量计算为(G2/G1)。在一些实施方案中,凝胶含量也可以通过在90℃下浸泡固化的聚合物组合物样品9小时,然后过滤固体部分,干燥,并记录重量来测量。
“溶解度测试”是指通过将聚合物/共聚物样品置于约10倍体积的烃溶剂如甲苯中,充分摇动并在室温下静置4小时来测量溶解度。然后,通过目测观察聚合物/共聚物是否完全或部分溶解来检查溶剂中的聚合物/共聚物。倾析或过滤内容物以测量剩余聚合物/共聚物的重量,干燥后,计算溶解的聚合物/共聚物的重量。
“溶胀含量”是指在甲苯中浸渍直到完全饱和(即样品重量在一段时间之后保持相同,不再吸收任何更多甲苯)之后的固化的聚合物组合物的重量(W2)与浸渍之前的可固化的聚合物组合物的重量(W1)的重量差(W%),如下计算:
W%=(W2-W1)/W1*100
Df表示“耗散因子”或“损耗角正切值”(Df),且是耗散系统中电能的损耗率的量度。
Dk表示介电常数或电容率。
本公开涉及一种可固化的聚合物组合物,其包含(i)二异烯基芳烃(DIAEA)和二乙烯基芳烃(DVA)的共聚物(DIAEA-DVA共聚物),和(ii)至少一种抗焦烧剂。在预期的固化步骤之前,可固化的聚合物组合物在诸如加工、储存、运输等步骤中不交联或具有最小的交联(过早交联)。可固化的聚合物组合物在固化时提供改善的电性能,例如Dk和Df。
DIAEA-DVA共聚物
所述共聚物公开和教导于美国专利申请公开2022/0195109A1中。DIAEA-DVA共聚物可由DIAEA和DVA单体通过在路易斯酸催化剂或布朗斯台德酸催化剂存在下的阳离子聚合获得。在一些实施方案中,共聚的DIAEA单体包含重复单元(A)、(B)、(C)和(D)中的至少一种,其结构如下所示,其中R1是H或C1-C8烷基。DIAEA-DVA共聚物可具有任何顺序的共聚的DIAEA和DVA单体的重复单元。
DIAEA-DVA共聚物可具有至少一个选自(E)、(F)、(G)和(H)的端基,其具有如下所示的结构:
用于制备共聚物的DIAEA单体的非限制性实例包括具有结构(I)1,3-二异烯基芳烃、(II)1,4-二异烯基芳烃或其混合物的化合物,其中R1是甲基、乙基、异丙基或正丁基。
在一些实施方案中,DIAEA选自二异丙烯基苯(DIPEB)和它们的用于制备共聚物的取代的变体。DIPEB的实例包括但不限于1,3-二异丙烯基苯、1,2-二异丙烯基苯、1,4-二异丙烯基苯、3,4-二环己基-1,2-二异丙烯基-苯、5-(3-甲基-环戊基)-1,3-二异丙烯基苯、3-环戊基-甲基-6-正丙基-1,4-二异丙烯基苯、4-(2-环丁基-1-乙基)-1,2-二异丙烯基苯、3-(2-正丙基环丙基)-1,4-二异丙烯基苯、2-甲基-5-正己基-1,3-二异丙烯基苯、4-甲基-1,2-二异丙烯基苯、5-乙基-1,3-二异丙烯基苯、3-甲基-1,4-二异丙烯基苯及其混合物。
在一些实施方案中,DVA选自二乙烯基苯(DVB)、二乙烯基萘、二乙烯基联苯、二乙烯基二苯醚及其混合物。DVB可以包括邻二乙烯基苯、对二乙烯基苯、间二乙烯基苯、三乙烯基苯或其混合物。
在一些实施方案中,所述共聚物进一步包含衍生自另一种可聚合单体的重复单元,所述另一种可聚合单体包括(i)环二烯或其二聚体,(ii)环二烯和非环二烯的加合物,(iii)具有两个或更多个烯丙基的烯丙基化合物,(iv)除DVA之外的具有两个或更多个乙烯基的乙烯基化合物,及其任何组合或子组合。
其它可聚合单体的实例包括1,3-环己二烯、1,4-环己二烯、1,3-环戊二烯、烷基环戊二烯、苯乙烯、α-甲基苯乙烯、对甲基苯乙烯、丁二烯、异戊二烯、戊间二烯、二乙烯基甲苯、二乙烯基吡啶、二乙烯基二甲苯、三乙烯基环己烷、乙基乙烯基苯、乙烯基萘、乙烯基三异丙烯氧基硅烷、甲氧基三乙烯基硅烷、四乙烯基硅烷、二乙氧基二乙烯基硅烷、2,4,6,8-四乙烯基-2,4,6,8-四甲基环四硅氧烷和2,4,6,8,10-五甲基-2,4,6,8,10-五乙烯基环五硅氧烷或其混合物。
在一些实施方案中,DIAEA-DVA共聚物是无规或嵌段共聚物中的任一种。或者,所述共聚物可以含有用DVA封端的DIAEA均聚物,以得到DVA封端的聚DIAEA。
所述共聚物可具有至少一个选自结构(E)、(F)、(G)和(H)的活性端基,且它可使用本领域已知的方法用各种官能团如异氰酸酯、环状酸酐、羧酸、羧酸酯或环氧基团适当地官能化。
在一些实施方案中,DIAEA-DVA共聚物的DIAEA与DVA的摩尔比为15:1-1:15,或12:1-1:12,或10:1-1:10,或8:1-1:8,或5:1-1:5,或4:1-1:4,或3:1-1:3,或2:1-1:2,或1:1。
在一些实施方案中,DIAEA-DVA共聚物的数均分子量(Mn)为1-10、1.5-8、或2-10、或1-5、或>1、或<10kg/mol;重均分子量(Mw)为3-70,或5-60,或7-55,或10-50kg/mol;多分散指数(PDI)为2-20、3-15、或2-10、或5-15。
在一些实施方案中,DIAEA-DVA共聚物以固体形式存在或作为在烃溶剂中的溶液存在,基于溶液的总重量,其浓度为20-75wt%、或30-75wt%、或>20wt%、或<75wt%。
在一些实施方案中,基于可固化的聚合物组合物的总重量,不包括玻璃纤维的量,所述可固化的聚合物组合物包含90-99.999wt%、或90-99.995wt%、或90-99.99wt%、或99-99.95wt%、或95-99.999wt%、或95-99.995wt%、或95-99.99wt%、或95-99.95wt%的DIAEA-DVA共聚物。
DIAEA-DVA共聚物的制备方法
DIAEA-DVA共聚物可以通过本领域已知的方法制备,并公开和教导于美国专利申请公开2022/0195109A1中。在一些实施方案中,共聚物通过在阳离子条件下在合适的溶剂中在催化剂例如布朗斯台德酸或路易斯酸存在下聚合DIAEA和DVA来制备。单体/共聚单体的加入可以在合适的温度下进行足够的时间,和聚合反应继续进行,直到所有的单体/共聚单体基本上消失,或者直到分析反应混合物表明已经形成了具有足够分子量的共聚物。在反应结束时,可以通过用水淬灭反应混合物,随后分离有机溶剂层并汽提溶剂来分离共聚物。在高真空下可以从产物中除去痕量有机物。
抗焦烧剂
抗焦烧剂防止在目标固化步骤之前共聚物中的乙烯基过早交联。抗焦烧剂可以允许在期望的较高温度下发生固化。抗焦烧剂的有效性可以通过焦烧延迟的持续时间、交联开始的温度和其对共聚物的固化程度的影响来确定。
在一些实施方案中,抗焦烧剂选自苯乙烯,α-甲基苯乙烯单体(AMSM),α-甲基苯乙烯二聚体(AMSD),α-甲基苯乙烯低聚物(AMSO),在至少一个酚OH基团的邻位被烷基、苯基等取代的受阻酚化合物,非受阻酚化合物,胺化合物,硫脲化合物,苯并咪唑,及其混合物和衍生物。α-甲基苯乙烯衍生物可具有位于每个环上的一个或多个官能团,且可全部相同或不同。
在一些实施方案中,α-甲基苯乙烯二聚体选自2,4-二苯基-4-甲基-1-戊烯、2,4-二苯基-4-甲基-2-戊烯、1,2-三甲基-3-苯基茚满、顺式-1,3-二甲基-1,3-二苯基环丁烯、反式-1,3-二甲基-1,3-二苯基环丁烯及其混合物。
在一些实施方案中,α-甲基苯乙烯衍生物具有式(J):
其中R2、R3、R4、R5、R6和R7各自独立选自氢、-CH(O)、-CN、异氰酸基、硫代异氰酸基、SO3H及其盐和酯、NR8R9、硅烷、卤素、C(O)OR10、-C(O)NR11R12、-CR13(O)、-C(O)OC(O)R14、-C(O)NR15COR16、-OC(O)R17、-OR18、取代和未取代的烷基、取代和未取代的烯基、取代和未取代的炔基、以及取代和未取代的芳基;R8、R9、R10、R11、R12、R13、R14、R15、R16和R17各自独立选自H、烷基、芳基、取代的烷基或取代的芳基;R18选自烷基、芳基、取代的烷基或取代的芳基;R2、R3、R4、R5、R6和R7不能同时都是氢。烷基和取代的烷基可具有由1-12个碳组成的链。还优选位于取代的烷基或取代的芳基上的取代基不含可显著干扰自由基聚合的官能团。
在一些实施方案中,抗焦烧剂基于不含任何杂原子或极性基团的烃。
抗焦烧剂的实例包括2,6-二叔丁基-对甲酚、2,2'-亚甲基-双-(4-甲基-6-叔丁基苯基)、4,4'-硫代-双-(6-叔丁基-3-甲基苯酚)、1,3,5-三甲基-2,4,6-三-(2',6'-二叔丁基-对甲苯基)苯、4,4'-亚丁基-双-(6-叔丁基-3-甲基苯酚)、(2,2,6,6-四甲基哌啶-1-基)氧基(TEMPO)、双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯(双-TEMPO)、4-丙烯酰氧基-2,2,6,6-四甲基哌啶-N-氧基(AOTEMPO)、1,1-二苯基乙烯(DPE)、4-甲基丙烯酰氧基-2,2,6,6-四甲基哌啶-N-氧基、4-肉桂酰氧基-2,2,6,6-四甲基哌啶-N-氧基、4-壬酰氧基-2,2,6,6-四甲基哌啶-N-氧基,1-环己氧基-2,2,6,6-四甲基哌啶-4-醇,1-甲氧基-2,2,6,6-四甲基哌啶-4-醇、1-环己氧基-2,2,6,6-四甲基哌啶-4-基丙烯酸酯、1-甲氧基-2,2,6,6-四甲基哌啶-4-基丙烯酸酯、2,5-二叔戊基氢醌、异十三烷基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯、C-13至C-15醇酯、3-(3,5-二叔丁基-4-羟基苯基)丙酸酯、聚(氧化烯)链取代的3-芳基苯并呋喃酮、聚(己内酯)链取代的3-芳基苯并呋喃酮、甲氧基烯丙基苯基烯丙基醚(MAPAE)、马来酸二丁酯、烯丙基丙二酸酯、各种单烯丙基化合物、马来酸壬酯、富马酸二乙酯、4-羟基苯乙烯、4-乙烯基苯胺、丁基化羟基甲苯(BHT)、茋醌、烷基化二苯胺、醌亚胺、受阻酚、双酚、硫代双酚、取代的氢醌、亚磷酸三(烷基苯基)酯、二烷基硫代二丙酸酯、苯基萘胺、取代的二苯胺、二烷基和烷基芳基和二芳基取代的对苯二胺、单体和聚合的二氢喹啉、2-(4-羟基-3,5-叔丁基苯胺)-4,6-双(辛基硫代)1,3,5-三嗪、六氢-1,3,5-三-β-(3,5-二叔丁基-4-羟基苯基)丙酰基-s-三嗪,2,4,6-三(正-1,4-二甲基戊基亚苯基-二氨基)-1,3,5-三嗪、三-(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯、二丁基二硫代氨基甲酸镍、2-巯基甲苯咪唑及其锌盐、石油蜡、四[亚甲基(3,5-二叔丁基-4-羟基氢肉桂酸酯)]甲烷、双[(β-(3,5-二叔丁基-4-羟苄基)-甲基羧乙基)]硫化物、4,4'-硫代双(2-甲基-6-叔丁基苯酚)、4,4'-硫代双(2-叔丁基-5-甲基苯酚)、2,2'-硫代二(4-甲基-6-叔丁苯酚)、硫代二亚乙基双(3,5-二叔丁基-4-羟基)氢肉桂酸酯、三(2,4-二叔丁基苯基)亚磷酸酯、二叔丁基苯基亚膦酸酯、硫代化合物(例如硫代二丙酸二月桂基酯、硫代二丙酸二肉豆蔻基酯和硫代二丙酸二硬脂基酯)、硅氧烷、聚合的2,2,4-三甲基-1,2-二氢喹啉、N,N’-双(1,4-二甲基戊基-对苯二胺)、烷基化二苯胺、4,4'-双(α,α-二甲基苄基)二苯胺、二苯基对苯二胺、混合的二芳基对苯二胺类、2,2'-草酰氨基双-(乙基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯)、2,2'-草酰氨基双-(乙基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯)、4,4'-异亚丙基二酚、苯基-β-萘胺、苯基-α-萘胺、二苯基对苯二胺、1,3-双-(二甲基氨基丙基)-2-硫脲及其混合物。
在一些实施方案中,抗焦烧剂是选自以下的金属盐:二甲基二硫代氨基甲酸铋、二戊基二硫代氨基甲酸镉、二乙基二硫代氨基甲酸镉、二甲基二硫代氨基甲酸铜、二戊基二硫代氨基甲酸铅、二甲基二硫代氨基甲酸硒、二乙基二硫代氨基甲酸碲、二乙基二硫代氨基甲酸铊、二戊基二硫代氨基甲酸锌、二乙基二硫代氨基甲酸锌、二甲基二硫代氨基甲酸锌、二甲基二硫代氨基甲酸硒及其混合物。
在一些实施方案中,可固化的聚合物组合物包含单一的抗焦烧剂或两种或更多种抗焦烧剂的混合物。抗焦烧剂的混合物可以具有至少一种基于α-甲基苯乙烯二聚体和/或基于不含任何杂原子或极性基团的烃的抗焦烧剂。
在一些实施方案中,抗焦烧剂在可固化的聚合物组合物中的加入量为0.001-10wt%、或0.005-10wt%、或0.010-10wt%、或0.050-10wt%、或0.001-5wt%、或0.005-5wt%、或0.010-5wt%、或0.050-5wt%,基于可固化的聚合物组合物的总重量,不包括玻璃纤维的量。
任选的组分
可固化的聚合物组合物还包含至少一种选自下述的添加剂:引发剂、活化剂、固化剂、稳定剂、中和剂、增稠剂、聚结剂、抗氧化剂、抗臭氧剂、变色pH指示剂、增塑剂、增粘剂、成膜添加剂、染料、颜料、交联剂、UV吸收剂、UV稳定剂、催化剂、填料、其它聚合物、纤维、阻燃剂、粘度调节剂、润湿剂、脱气剂、增韧剂、粘附促进剂、着色剂、热稳定剂、润滑剂、流动改性剂、防滴剂、抗静电剂、加工助剂、促进剂、防水剂、热导率赋予剂、电磁波屏蔽性能赋予剂、荧光剂、自由基清除剂、及其混合物。
促进剂的非限制性实例包括二苯并噻唑、N-环己基-2-苯并噻唑、N-环己基-2-苯并噻唑亚磺酰胺(CBS)、N,N-二环己基-2-苯并噻唑亚磺酰胺(DCBS)、硫代氨基甲酰基亚磺酰胺、2-(4-吗啉代硫代)-苯并噻唑(MBS)、N-氧二亚乙基硫代氨基甲酰基-N-氧二乙基磺酰胺(OTOS)、2-巯基苯并噻唑(MBT)、2,2'-二硫代双(苯并噻唑)(MBTS)、二硫化四甲基秋兰姆(TMTD)、N-叔丁基-2-苯并噻唑磺酰胺(TBBS)、四硫化双五亚甲基秋兰姆(DPTT)、4,4'-二硫代二吗啉(DTDM)、二甲基二硫代氨基甲酸锌、硫脲、黄原酸酯、硫代磷酸酯、2-巯基苯并噻唑锌盐(ZMBT)、2-(4-吗啉代二硫代)苯并噻唑(MDB)、二乙基硫代氨基甲酰基-2-巯基苯并噻唑及其混合物。
在一些实施方案中,可固化的聚合物组合物进一步包含选自下述的热引发剂或辐射引发剂:氢过氧化物、液体过氧化二碳酸酯、过氧化二烷基、二过氧化缩酮、单过氧化碳酸酯、环酮过氧化物、过氧化二酰基、过氧化二枯基(DCP)、过氧化叔丁基枯基、过氧化有机磺酰基、1,3-双-(叔丁基过氧异丙基)苯、2,5-二甲基-2,5-二-(叔丁基过氧)己烷、2,5-二甲基-2,5-(叔丁基过氧)己烷-3,2,5-二甲基-2,5-二(叔戊基过氧)己烷、2,5-二(叔丁基过氧)-2,5-二甲基-3-己炔、过氧化二叔丁基、α,α-二[(叔丁基过氧)-异丙基]苯、过氧化二叔戊基、1,3,5-三-[(叔丁基过氧)异丙基]苯、过氧酯、1,1-二(叔丁基过氧)-3,3,5-三甲基环己烷、1,1-二(叔丁基过氧)环己烷、4,4-二(叔丁基过氧)戊酸正丁酯、3,3-二(叔丁基过氧)丁酸乙酯、3,3-三(叔戊基过氧)丁酸乙基、2,2-二(叔戊基过氧)丙烷、3,6,6,9,9-五甲基-3-正丁基-1,2,4,5-四氧杂环壬烷、3,6,6,9,9-五甲基-3-乙氧基羰基甲基-1,2,4,5-四氧杂环壬烷及其混合物。
在一些实施方案中,添加剂的用量为0.1-10wt%、或0.5-8wt%、或0.1-5wt%,基于可固化的聚合物组合物的总重量。
在一些实施方案中,可固化的聚合物组合物还包含除DIAEA-DVA共聚物以外的聚合物。这些其它聚合物的实例包括1,2-聚丁二烯、聚异戊二烯、聚丁二烯-聚异戊二烯共聚物、聚丁二烯-聚苯乙烯-聚二乙烯基苯三元共聚物、聚苯醚、可固化的环烯烃或它们的共聚物、聚丙烯酸酯、聚二环戊二烯、苯乙烯-异戊二烯-苯乙烯共聚物、丁二烯-丙烯腈共聚物、丙烯腈-苯乙烯树脂、丙烯腈-丁二烯-苯乙烯树脂、聚酯、苯乙烯嵌段共聚物、聚烯烃、聚四氟乙烯(PTFE)、聚醚酰亚胺(PEI)、马来酰亚胺树脂、氰酸酯树脂、环氧树脂、酚醛树脂、苯并噁嗪树脂、聚酰胺树脂、聚酰亚胺树脂、聚苯醚、聚苯硫醚、聚缩醛、聚砜、聚酯酰亚胺、聚醚砜、聚醚酮、氟树脂、及其混合物。
在一些实施方案中,可固化的聚合物组合物还包含选自下述的橡胶状聚合物:天然橡胶(NR)、丁基橡胶、卤化丁基橡胶和EPDM(三元乙丙橡胶)、丁苯橡胶(SBR)、丁二烯橡胶、合成聚异戊二烯橡胶、环氧化天然橡胶、聚丁二烯橡胶、高顺式聚丁二烯橡胶、三元乙丙橡胶、乙丙橡胶、马来酸改性的乙丙橡胶、异丁烯-芳族乙烯基或二烯单体共聚物、溴化-NR、氯化-NR、溴化异丁烯对甲基苯乙烯共聚物、氯丁二烯橡胶、表氯醇均聚物橡胶、表氯醇-环氧乙烷或烯丙基缩水甘油醚共聚物橡胶、表氯醇-环氧乙烷-烯丙基缩水甘油醚三元共聚物橡胶、氯磺化聚乙烯、氯化聚乙烯、马来酸改性的氯化聚乙烯、甲基乙烯基硅橡胶、二甲基硅橡胶、甲基苯基乙烯基硅橡胶、聚硫橡胶、偏二氟乙烯橡胶、四氟乙烯-丙烯橡胶、氟化硅橡胶、氟化磷原橡胶、苯乙烯弹性体、热塑性烯烃弹性体、聚酯弹性体、氨基甲酸酯弹性体、聚酰胺弹性体、及其混合物。
基于所需的最终用途应用,可将任何合适量的其它聚合物和/或橡胶状聚合物掺入到所述可固化的聚合物组合物中。如果使用,基于可固化的聚合物组合物的总重量,不包括玻璃纤维的量,此类聚合物的量为10-99wt%、或15-95wt%、或20-70wt%、或25-60wt%、或30-55wt%、或>25wt%、或<50wt%。
可固化的聚合物组合物的制备方法
可固化的聚合物组合物可通过本领域已知的任何方法制备,例如配混、共混或在溶液中制备。在一些实施方案中,通过混合组合物的所有组分来配混可固化的聚合物组合物。可通过任何常规的混合或配混操作,例如单螺杆和双螺杆挤出机,实现配混。可选择混合温度,以使获得各组分的均匀共混物,且在冷却后保持,而没有过早交联。
在一些实施方案中,可固化的聚合物组合物包含共聚物、抗焦烧剂和任选的组分的混合物。可以向该混合物中加入交联剂,并进行组合物的固化。
在一些实施方案中,将抗焦烧剂与任选的组分一起加入到共聚物中以形成可固化的聚合物组合物,随后加入交联剂,然后使组合物进行固化。
在一些实施方案中,可固化的聚合物组合物通过将所有组分在烃溶剂例如甲苯中混合并搅拌足够的时间以获得溶液中的可固化的聚合物组合物来制备。基于溶液的总重量,可固化的聚合物组合物在烃溶剂中的浓度(总固体含量)可以为10-80wt%、或20-75wt%、或25-80wt%、或30-75wt%、或>20wt%、或<75wt%。
可固化的聚合物组合物可以原样使用,例如在溶剂中,或者可以制成用于下游最终用途应用的膜,例如固化/或交联的以用于CCL应用等。
在一些实施方案中,制备包含DIAEA-DVA共聚物和任选的组分但不包含抗焦烧剂的聚合物组合物。该聚合物组合物可用于与可固化的聚合物组合物比较某些性能。
可固化的聚合物组合物的固化
可固化的聚合物组合物可通过使用外源例如热、紫外光(UV)、可见光、电子束或它们的组合来固化,以获得固化的聚合物组合物。组合物的固化可以在有或没有引发剂的情况下进行。
在一些实施方案中,可固化的聚合物组合物的固化在140-250℃、或145-220℃、或150-210℃、或155-200℃、或>140℃或>150℃的温度下进0.5-60分钟、或1-50分钟、或5-40分钟或10-30分钟。
在一些实施方案中,可固化的聚合物组合物在比不含抗焦烧剂的聚合物组合物的固化温度高至少30℃的温度下固化。在一些实施方案中,可固化的聚合物组合物在比不含抗焦烧剂的聚合物组合物的固化温度高至少35℃、或至少40℃、或至少45℃的温度下固化。
在一些实施方案中,固化后,DIAEA-DVA共聚物中>60%、或>65%、或>70%、或>75%、或>80%、或>85%、或>90%、或>99%的乙烯基被交联步骤消耗(基于固化前存在于DIAEA-DVA共聚物中的总乙烯基)。
DIAEA-DVA共聚物和可固化的聚合物组合物的性能
在一些实施方案中,DIAEA-DVA共聚物是具有分子量范围和相对宽的分子量分布(多分散指数)的良好结合的树脂材料,该良好结合部分地使该树脂材料更可溶于非极性溶剂中,从而增强其可加工性。
在一些实施方案中,基于溶剂的总重量,DIAEA-DVA共聚物在25℃下在烃溶剂中小于4小时的溶解度为至少10wt%、或>20wt%、或>30wt%、或>50wt%、或>70wt%、或<99wt%、或10-75wt%、或20-65wt%、或10-60wt%。溶剂的实例包括己烷、庚烷、辛烷、异辛烷、环己烷、清漆与油漆用石脑油(VM&P石脑油)、石油醚、甲苯、二甲苯及其混合物。
在一些实施方案中,作为固体的DIAEA-DVA共聚物当溶解在烃溶剂中时形成基本上无凝胶的溶液,其中<2wt%、或<5wt%、或<10wt%、或<15wt%的固体保持不溶于所述溶剂。
在一些实施方案中,基于共聚物的总重量,在烃溶剂中的DIAEA-DVA共聚物溶液的凝胶含量为0.05-5wt%,或0.1-4.5wt%,或1-4wt%,或<5wt%、或<2wt%、或<1wt%。
在一些实施方案中,DIAEA-DVA共聚物的分解开始温度为200-450℃,或220-420℃,或240-400℃,或<600℃,或<500℃或>300℃。
在一些实施方案中,根据ASTM D3418或DMA(动态力学分析仪),使用差示扫描比色法(DSC)测量,DIAEA-DVA共聚物的玻璃化转变温度(Tg)为50-300℃,或60-250℃,或70-220℃,或80-200℃,或100-250℃,或120-220℃,或>150℃,或<250℃,或<200℃。
在一些实施方案中,DIAEA-DVA共聚物的吸湿系数为<0.1,或<0.08,或<0.05,在25℃下根据ASTM D570测量。
在一些实施方案中,DIAEA-DVA共聚物的密度为>0.9,或>1.0,或1.0-2.0,或1.0-1.50g/cc。
在一些实施方案中,在40℃下储存1天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物在25℃下的溶液粘度比不含抗焦烧剂的聚合物组合物的溶液粘度低至少20%、或低至少30%、或低至少40%。
在一些实施方案中,在40℃下老化50天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物的溶液粘度与初始溶液粘度(老化前)相比增加<30%、或<25%、或<20%、或<15%。
在一些实施方案中,在40℃下老化100天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物的溶液粘度与初始溶液粘度(老化前)相比增加<50%、或<45%、或<40%、或<35%。
在一些实施方案中,在40℃下老化181天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物的溶液粘度与初始溶液粘度(老化前)相比增加<50%、或<45%、或<40%。
在一些实施方案中,可固化的聚合物组合物的凝胶点为>125℃,或>130℃,或>132℃,或>135℃,或>138℃,或>140℃,使用Discovery Hybrid Rheometer(DHR)在120℃干燥5分钟的可固化的聚合物组合物的膜样品上测量。
在一些实施方案中,可固化的聚合物组合物的凝胶点>135℃,或>140℃,或>145℃,或>150℃,使用Discovery Hybrid Rheometer(DHR)在35℃干燥5分钟的膜样品上测量。
在一些实施方案中,使用Discovery Hybrid Rheometer(DHR),在120℃干燥5分钟的膜样品上测量,可固化的聚合物组合物的凝胶点比不含抗焦烧剂的聚合物组合物的凝胶点高至少10%、或至少15%、或至少20%。
固化的聚合物组合物的性能
由于优异的交联特性,可以获得具有高实际应用性的固化的聚合物组合物而不发生不期望的焦烧现象。固化的聚合物组合物具有不同程度的韧性、柔性、良好的化学和氧化稳定性以及增强的阻燃性,可用于电子应用。
在一些实施方案中,固化的聚合物组合物的Dk(电容率)为<2.7,或<2.65,或<2.60,或<2.55,在10GHz下根据ASTM D2520测量。
在一些实施方案中,固化的聚合物组合物的Df(损耗角正切值)为<0.006、或<0.005、或<0.004、或0.003-0.0001、或0.002-0.0001,在10GHz下根据ASTM D2520测量。
在一些实施方案中,在固化过程期间,可固化的聚合物组合物的放热能值为>80,或>100,或>120,或>140,或>160,或>180,或>200J/g,或60-220,或80-210,或100-200J/g。所述放热能是交联度的指示,其可通过分析放热峰来测量,所述放热峰通过使用差示扫描量热计(DSC)以10℃/min的速率将温度从室温升高到300或400℃获得。
固化的聚合物组合物对金属例如铝、铜等具有良好的粘附性。在一些实施方案中,固化的聚合物组合物对金属的180°剥离强度为0.1-1.0,或0.2-0.9,或0.3-0.7N/m。
在一些实施方案中,基于固化的聚合物组合物的总初始重量,固化的聚合物组合物在室温下的溶胀含量为<30%、或<25%、或<20%、或<15%、或<10%、或<5%、或0-30%、或0-20%、或0-10%。
在一些实施方案中,基于固化的聚合物组合物的总初始重量,固化的聚合物组合物在90℃下的溶胀含量为<30%、或<25%、或<20%、或<15%、或<10%、或<7%、或0-30%、或0-20%、或0-10%。
在一些实施方案中,基于固化的聚合物组合物的总重量,固化的聚合物组合物在室温下4小时后的凝胶含量为>85%、或>88%、或>90%、或>95%、或>98%、或>99%、或多达100%。
在一些实施方案中,基于固化的聚合物组合物的总重量,固化的聚合物组合物在90℃下9小时后的凝胶含量为>85%、或>88%、或>90%、或>95%、或>98%、或>99%、或多达100%。
在一些实施方案中,含有40wt%玻璃纤维(基于固化的聚合物组合物的总重量)的固化的聚合物组合物的热膨胀系数(CTE)在XY平面中为5-40、或10-25、或15-20ppm/℃,在Z方向上为30-120、或40-95、或45-85ppm/℃,使用DMA在-50至300℃的范围内测量。
可固化的聚合物组合物的应用
可固化的聚合物组合物可用于汽车的涂覆应用,例如修补、底漆、底涂层、罩涂层、透明涂层等。电力电缆可由可固化的聚合物组合物获得,特别是高压应用中的电缆,且在交流(AC)和直流(DC)应用中都有用。
可固化的聚合物组合物可有价值的用作覆金属层压板,例如覆铜层压板(CCL)、电器外壳、电缆、电连接器、电子开关和电子部件,例如印刷电路板(PCB)、印刷线路板和柔性印刷电路(FPC)。
用于制备PCB的预浸料可以使用可固化的聚合物组合物结合橡胶组分和任选的添加剂通过本领域已知的方法来制备。在一些实施方案中,可固化的聚合物组合物包含用于制备PCB的玻璃纤维。玻璃纤维可以用有机硅氧烷例如聚烷基硅氧烷、聚芳基硅氧烷等预处理,以增加玻璃纤维和共聚物之间的粘附性。
在一些实施方案中,CCL包括布置在由固化的聚合物组合物制成的绝缘层的一侧或两侧上的金属箔。此外,CCL可以包括布置在与绝缘层接触的表面侧的阻挡层。阻挡层可以包含能够降低传输损耗的金属,例如钴。阻挡层可以通过镀覆工艺形成,例如溅射、电镀或化学镀。可通过堆叠单个层压板并对其进行加热,例如在110-220℃、120-210℃或125-180℃的温度和0.5-20、或1-18、或2-15或5-12MPa的压力下持续10分钟至5小时或20分钟至2小时,来制备所需厚度的堆叠层压板。
实施例
以下实施例是非限制性的。
可固化的聚合物组合物的溶液粘度通过布鲁克菲尔德粘度计测量。在烃溶剂中的浓度是总固体含量,例如,具有或不具有抗焦烧剂的共聚物。基于溶液的总重量,浓度可以在10-80wt%的范围内。
流变性能,例如凝胶点,通过使用来自TA Instruments的Discovery HybridRheometer(DHR)测量。
实施例中使用的组分包括:
抗焦烧剂-1(ASA-1)是含硫的酚类化合物。
抗焦烧剂-2(ASA-2)是含氮环状化合物。
实施例1
制备1,3-DIPEB和1,3-二乙烯基苯的共聚物。在3升3颈烧瓶中,装入921g环己烷并加热至65℃,在连续搅拌下加入0.0125g三氟甲磺酸。在30分钟内加入64.5g 1,3-DIPEB、185.7g 1,3-二乙烯基苯和250g环己烷的混合物。加入混合物后,用750mL水和2g NaHCO3猝灭反应物质,然后在65℃下再加热反应物质15分钟。从底部除去水层。用水洗涤剩余的有机层几次。通过除去溶剂回收共聚物产物。
实施例2
用50wt%浓度的实施例1的共聚物和抗焦烧剂(以不同的量)在甲苯中制备可固化的聚合物组合物。使样品在烘箱中在不同温度和不同持续时间下老化。通过目视观察样品和不含抗焦烧剂的对比例2a进行粘度变化的评价。表1显示了各种样品在视觉观察后的数据和结果。
表1
U-粘度不变,V-粘度增加,G-胶凝为固体。
实施例3
通过将在甲苯中浓度为70wt%的实施例1中的共聚物和不同的抗焦烧剂(以不同的量)混合,然后溶剂流延到硅基材上,制备可固化的聚合物组合物的膜样品。将100微米厚的各薄膜在室温下干燥1小时,然后在120℃干燥5分钟。然后从硅基材上取下膜样品,使用DHR测量凝胶点。结果示于表2。实施例3a为对比例。
表2
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实施例4
在甲苯中用72.5wt%浓度的实施例1的共聚物和抗焦烧剂(以不同的量)制备可固化的聚合物组合物。将这些样品在40℃的烘箱中老化长达181天。对每个样品进行目测观察,并通过使用DHR在25℃下测量粘度,结果示于表3中,实施例4a为对比例。
表3
实施例5
对通过重复实施例3的工序制备的膜样品进行凝胶点测量,不同之处在于使用两种抗焦烧剂的组合。使每个膜在室温下干燥1小时,然后在35℃或120℃干燥5分钟。然后从硅基材上取下膜样品,使用DHR测量凝胶点,结果如表4所示,每个膜的厚度为100微米。实施例5a和5f为对比例。
表4
实施例6
制备固化的聚合物组合物。将实施例5的样品5f和5i分别与0.5wt%的过氧化二枯基共混。将各样品置于模具中,在100℃下8000psi下压制5分钟,然后在180℃下20000psi下压制2小时。测量样品的凝胶含量(室温4小时)、溶胀含量(室温4小时)、Dk和Df。结果示于表5中。
表5
本文所用的术语“包含/包括”意为包括在该术语之后确定的要素或步骤,但任何此类要素或步骤不是穷举的,且实施方案可包括其它要素或步骤。虽然术语“包含”和“包括”在本文中已用于描述各个方面,但术语“基本上由...组成”和“由...组成”可代替“包含”和“包括”使用以提供本公开内容的更具体方面且也被公开。
Claims (15)
1.一种可固化的聚合物组合物,其包含:
(i)二异烯基芳烃和二乙烯基芳烃的共聚物,其中所述共聚物具有下述特征:
二异烯基芳烃与二乙烯基芳烃的摩尔比为1:15-15:1,
在25℃下在烃溶剂中小于4小时的溶解度为至少10wt%,根据说明书中所述的溶解度试验测量,
玻璃化转变温度(Tg)为50-300℃,根据ASTM D3418测量,和
基于所述共聚物的总重量,凝胶含量为小于5wt%,根据说明书中所述的凝胶含量测试测量;和
(ii)基于所述可固化的聚合物组合物的总重量,0.001-10wt%的选自下述的抗焦烧剂:苯乙烯、α-甲基苯乙烯单体、α-甲基苯乙烯二聚体、α-甲基苯乙烯低聚物、受阻酚类化合物、非受阻酚类化合物、苯并咪唑、及其混合物;和
其中,在40℃下储存1天后,在甲苯中浓度为72.5wt%的可固化的聚合物组合物的在25℃下通过Brookfield粘度计测量的溶液粘度比不含所述抗焦烧剂的聚合物组合物的溶液粘度低至少20%。
2.根据权利要求1所述的可固化的聚合物组合物,其中所述可固化的聚合物组合物具有10∶1-1∶10摩尔比的二异烯基芳烃与二乙烯基芳烃。
3.根据权利要求1所述的可固化的聚合物组合物,其中所述共聚物在25℃下在烃溶剂中小于4小时的溶解度为10-75wt%。
4.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述共聚物的凝胶含量为0.05-5wt%。
5.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述共聚物的玻璃化转变温度为100-250℃。
6.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述可固化的聚合物组合物的溶液粘度比不含所述抗焦烧剂的聚合物组合物的溶液粘度低至少30%。
7.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述可固化的聚合物组合物具有以下特征中的至少一个:
在120℃下干燥5分钟的可固化的聚合物组合物的膜上测量的凝胶点大于125℃;和
在35℃下干燥5分钟的可固化的聚合物组合物的膜上测量的凝胶点大于140℃。
8.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中在120℃下干燥5分钟的可固化的聚合物组合物的膜上测量,所述可固化聚合组合物的凝胶点比不含所述抗焦烧剂的聚合物组合物的凝胶点高至少10%。
9.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述二异烯基芳烃选自1,3-二异丙烯基苯、1,2-二异丙烯基苯、1,4-二异丙烯基苯、3,4-二环己基-1,2-二异丙烯基苯、5-(3-甲基-环戊基)-1,3-二异丙烯基苯、3-环戊基-甲基-6-正丙基-1,4-二异丙烯基苯、4-(2-环丁基-1-乙基)-1,2-二异丙烯基苯、3-(2-正丙基环丙基)-1,4-二异丙烯基苯、2-甲基-5-正己基-1,3-二异丙烯基苯、4-甲基-1,2-二异丙烯基苯、5-乙基-1,3-二异丙烯基苯、3-甲基-1,4-二异丙烯基苯及其混合物;和
其中所述二乙烯基芳烃选自二乙烯基苯、二乙烯基萘、二乙烯基联苯、二乙烯二苯基醚及其混合物。
10.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中所述共聚物的数均分子量(Mn)为1-10kg/mol,重均分子量(Mw)为3-70kg/mol,和多分散指数为2-20。
11.根据权利要求1-3中任一项所述的可固化的聚合物组合物,其中,基于所述可固化的聚合物组合物的总重量,所述可固化的聚合物组合物包含0.010-5wt%的抗焦烧剂。
12.一种固化的聚合物组合物,其通过在大于140℃的温度下固化权利要求1-3中任一项所述的可固化的聚合物组合物而获得,其中所述固化的聚合物组合物的特征在于具有下述特性:
凝胶含量大于90%,根据说明书中所述的凝胶含量测试进行测量,和
小于2.7的介电常数(Dk)和小于0.006的耗散因子(Df),均根据ASTM D2520在10GHz下测量。
13.根据权利要求12所述的固化的聚合物组合物,其中所述可固化的聚合物组合物在比不含所述抗焦烧剂的聚合物组合物的固化温度高至少30℃的温度下固化。
14.根据权利要求12-13中任一项所述的固化的聚合物组合物,其中所述固化的聚合物组合物具有以下特征中的至少一个:
溶胀含量小于30%,和
凝胶含量大于95%。
15.根据权利要求12-13中任一项所述的固化的聚合物组合物,其中所述固化的聚合物组合物的介电常数(Dk)为<2.6和耗散因子(Df)为<0.005,均根据ASTM D2520在10GHz下测量。
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