TWI833009B - 芳香族胺樹脂、馬來醯亞胺樹脂、硬化性樹脂組成物及其硬化物 - Google Patents
芳香族胺樹脂、馬來醯亞胺樹脂、硬化性樹脂組成物及其硬化物 Download PDFInfo
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- TWI833009B TWI833009B TW109112558A TW109112558A TWI833009B TW I833009 B TWI833009 B TW I833009B TW 109112558 A TW109112558 A TW 109112558A TW 109112558 A TW109112558 A TW 109112558A TW I833009 B TWI833009 B TW I833009B
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- Prior art keywords
- resin
- aromatic amine
- acid
- bis
- maleimide
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 148
- 239000011347 resin Substances 0.000 title claims abstract description 148
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 45
- 239000011342 resin composition Substances 0.000 title claims abstract description 45
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims abstract description 30
- -1 aniline compound Chemical group 0.000 claims description 102
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims description 7
- OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical compound O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 9
- 229920000049 Carbon (fiber) Polymers 0.000 abstract description 7
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- 238000007789 sealing Methods 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 26
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
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- 230000000052 comparative effect Effects 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000003566 sealing material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 239000004643 cyanate ester Substances 0.000 description 7
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 7
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- TYMZLIDQEUWXEL-UHFFFAOYSA-N bis(2,3-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(OP(O)(=O)OC=2C(=C(C)C=CC=2)C)=C1C TYMZLIDQEUWXEL-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
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- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
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- 230000007423 decrease Effects 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
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- BVKSYBQAXBWINI-LQDRYOBXSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]propanoy Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCCN=C(N)N BVKSYBQAXBWINI-LQDRYOBXSA-N 0.000 description 3
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- 229910052723 transition metal Inorganic materials 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
Abstract
本發明的目的在於提供一種溶劑溶解性優異的具有特定結構的芳香族胺樹脂。進而,本發明的目的在於提供一種硬化性樹脂組成物及其硬化物,其可較佳地用於電氣電子零件的密封或電路基板、碳纖維複合材等,耐熱性高、低介電特性優異且含有由具有特定結構的芳香族胺衍生的馬來醯亞胺樹脂。一種芳香族胺樹脂,其由下述式(1)所表示。式(1)中,R1
、R2
、R3
表示碳數1~18的烴基。m表示1~4的整數,n表示平均值,且1≦n≦20。
Description
本發明是有關於一種芳香族胺樹脂及由其衍生的馬來醯亞胺樹脂、使用它們的硬化性樹脂組成物以及其硬化物,可較佳地用於半導體密封材、印刷配線基板、增層積層板等電氣電子零件、或碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度材料中。
近年來,搭載電氣電子零件的積層板由於其利用領域的擴大,要求特性廣泛且高度化。現有的半導體晶片的主流為搭載於金屬製的引線框架,但中央處理裝置(以下表示為CPU(中央處理單元(central processing unit)))等處理能力高的半導體晶片大多搭載於由高分子材料製成的積層板。
特別是於智慧型電話等中所使用的半導體封裝(package)(以下表示為PKG)中,為了應對小型化、薄型化及高密度化的要求,而要求PKG基板的薄型化,但若PKG基板變薄,則剛性會降低,因此藉由將PKG焊接安裝至母板(印刷電路板(printed circuit board,PCB))時的加熱而會導致產生大的翹曲等不良情況。為了減少該方面,要求焊接安裝溫度以上的高Tg的PKG基板材料。
此外,當前正加速開發的第五代通訊系統「5G」預計會進一步推進大容量化及高速通訊。低介電損耗正切材料的需求越來越高,至少要求1 GHz下0.005以下的介電損耗正切。
進而,於汽車領域中電子化在發展,有時亦於發動機驅動部附近配置精密電子設備,因此要求更高水準的耐熱耐濕性。電車或空調等中開始使用SiC半導體,對於半導體元件的密封材要求極高的耐熱性,因此現有的環氧樹脂密封材變得無法應對。
於此種背景下,正研究可兼具耐熱性及低介電損耗正切特性的高分子材料。例如,專利文獻1中提出有包含馬來醯亞胺樹脂及含丙烯基的酚樹脂的組成物。然而,另一方面,由於硬化反應時不參與反應的酚性羥基殘存,因此不可謂之電氣特性充分。另外,專利文獻2中揭示有利用烯丙基取代羥基的烯丙基醚樹脂。然而,顯示出於190℃下引起克萊森重排(Claisen Rearrangement),於一般的基板的成型溫度即200℃下,生成無助於硬化反應的酚性羥基,因此無法滿足電氣特性。
[現有技術文獻]
[專利文獻]
[專利文獻1]日本專利特開平04-359911號公報
[專利文獻2]國際公開2016/002704號
[發明所欲解決之課題]
本發明是鑒於此種狀況而完成,其目的在於提供一種顯示優異的耐熱性及電氣特性、具有良好的硬化性的芳香族胺樹脂、硬化性樹脂組成物及其硬化物。
[解決課題之手段]
本發明者等人為解決所述課題而進行了深入研究,結果發現新穎的芳香族胺樹脂。另外發現,含有由芳香族胺樹脂衍生的馬來醯亞胺樹脂的硬化性樹脂組成物的硬化物的耐熱性、低介電特性優異,從而完成了本發明。
即,本發明是有關於下述[1]~[9]。
[1]
一種芳香族胺樹脂,其由下述式(1)所表示。
[化1]
(式(1)中,R1
、R2
、R3
表示碳數1~18的烴基。m表示1~4的整數,n表示平均值,且1≦n≦20)。
[2]
如前項[1]所述的芳香族胺樹脂,其是使於2,6-位進行了取代的苯胺系化合物與烷基苯甲醛樹脂反應而獲得。
[3]
如前項[1]或[2]所述的芳香族胺樹脂,其由下述式(2)所表示。
[化2]
(式(2)中,n表示平均值,且1≦n≦20)。
[4]
如前項[3]所述的芳香族胺樹脂,其是使2-乙基-6-甲基苯胺與二甲苯甲醛樹脂反應而獲得。
[5]
如前項[1]至[4]中任一項所述的芳香族胺樹脂,其軟化點為80℃以下。
[6]
如前項[1]至[5]中任一項所述的芳香族胺樹脂,其重量平均分子量為300~700。
[7]
一種馬來醯亞胺樹脂,其是藉由使如前項[1]至[6]中任一項所述的芳香族胺樹脂與馬來酸或馬來酸酐反應而獲得。
[8]
一種硬化性樹脂組成物,含有如前項[7]所述的馬來醯亞胺樹脂。
[9]
一種硬化物,其是將如前項[8]所述的硬化性樹脂組成物硬化而獲得。
[發明的效果]
本發明的芳香族胺樹脂具有尖銳的分子量分佈,因此溶劑溶解性及處理性優異,作為馬來醯亞胺樹脂等的原料亦非常有用。
另外,含有由本發明的芳香族胺樹脂衍生的馬來醯亞胺樹脂的硬化性樹脂組成物的硬化物具有耐熱性高、低介電特性優異的特性,對於電氣電子零件的密封或電路基板、碳纖維複合材等有用。
本發明的芳香族胺樹脂由下述式(1)所表示。
[化3]
(式(1)中,R1
、R2
、R3
表示碳數1~18的烴基。m表示1~4的整數,n表示平均值,且1≦n≦20)。
所述式(1)中,R1
、R2
、R3
為碳數1~3的烴基時較佳,m為1或2時較佳。
本發明的芳香族胺樹脂由下述式(2)所表示時特佳。
[化4]
(式(2)中,n表示平均值,且1≦n≦20)。
另外,n較佳為1≦n≦10,進而佳為1≦n≦5。
本發明的芳香族胺樹脂於重量平均分子量不會過大、分子量分佈尖銳的方面具有優點。本發明的芳香族胺藉由使用於2,6-位具有取代基的苯胺作為原料,分子量分佈變得尖銳。
本發明的芳香族胺的重量平均分子量較佳為300~700,進而佳為400~600。分子量分佈可藉由凝膠滲透層析法(gel permeation chromatography,GPC)進行測定。於以重量平均分子量超過700的胺樹脂為原料來合成馬來醯亞胺樹脂的情況下,由於其分子量的大小及極性的高低,難以藉由水洗進行精製,且難以去除酸觸媒等雜質。若重量平均分子量小於300,則製成清漆時的溶劑穩定性有可能下降。
本發明的芳香族胺樹脂的製法並無特別限定。例如,可使2,6-位經取代的苯胺系化合物與烷基苯甲醛(alkylbenzene formalin)樹脂於鹽酸或活性白土等酸觸媒下反應,亦可使2,6-位經取代的苯胺系化合物、甲醛及烷基苯類於鹽酸或活性白土等酸觸媒下反應。於以鹽酸為觸媒的情況下,利用氫氧化鈉或氫氧化鉀等鹼金屬進行中和,利用甲苯或二甲苯等芳香族烴溶媒萃取後,水洗至排水變為中性,使用蒸發器等蒸餾除去溶劑,藉此可獲得目標芳香族胺樹脂。
作為所述2,6-位經取代的苯胺系化合物,可列舉2,6-二甲基苯胺、2,6-二乙基苯胺、2,6-二丙基苯胺、2,6-二異丙基苯胺、2-乙基-6-甲基苯胺、2-甲基-6-丙基苯胺、2-異丙基-6-甲基苯胺、2-乙基-6-丙基苯胺、2-乙基-6-異丙基苯胺等,但並不限定於該些。若碳數多,則溶劑溶解性提高,但耐熱性降低,因此較佳為經碳數1~3的烷基取代,更佳為經碳數1~2的烷基取代,最佳為2-乙基-6-甲基苯胺。
作為所述烷基苯甲醛樹脂,可列舉甲苯甲醛樹脂、鄰二甲苯甲醛樹脂、間二甲苯甲醛樹脂、對二甲苯甲醛樹脂、1,2,3-三甲基苯甲醛樹脂、1,2,4-三甲基苯甲醛樹脂、1,2,5-三甲基苯甲醛樹脂、1,3,5-三甲基苯甲醛樹脂、1,2,3,4-四甲基苯甲醛樹脂、1,2,3,5-四甲基苯甲醛樹脂、1,2,4,5-四甲基苯甲醛樹脂、1,3,5-三乙基苯甲醛樹脂、1,3,5-三丙基苯甲醛樹脂、1,3,5-三異丙基苯甲醛樹脂、1,3,5-三丁基苯甲醛樹脂、1,3,5-三-第三丁基苯甲醛樹脂等,但並不限於此。該些可單獨使用,亦可併用兩種以上。就介電特性及耐熱性的觀點而言,較佳為經碳數1~5的烴基取代,更佳為以經碳數1~3的烴基取代為佳,進而佳為以經甲基取代為佳。隨著烴基的碳數增加,分子的剛直性難以保證,分子容易振動,因此成為使介電特性或耐熱性降低的原因。相對於所使用的苯胺1重量%,烷基苯甲醛樹脂的使用量通常為0.05重量%~0.8重量%,較佳為0.1重量%~0.6重量%。
2-乙基-6-甲基苯胺與二甲苯甲醛樹脂的反應時,視需要,除了鹽酸、磷酸、硫酸、甲酸、對甲苯磺酸、甲磺酸以外,亦可列舉氯化鋁、氯化鋅等路易斯酸,活性白土、酸性白土、白碳、沸石、二氧化矽氧化鋁等固體酸,酸性離子交換樹脂等。該些可單獨使用,亦可併用兩種以上。就製造步驟的簡便性、經濟性的觀點而言,較佳為使用能夠再利用的固體酸(活性白土、酸性白土、白碳、沸石、二氧化矽氧化鋁等固體酸、酸性離子交換樹脂等)。相對於所使用的2,6-位經取代的苯胺系化合物1莫耳,觸媒的使用量通常為0.1莫耳~0.8莫耳,較佳為0.2莫耳~0.7莫耳。若過多,則反應溶液的黏度過高,攪拌可能會變得困難,若過少,則反應的進行可能會變慢(關於使用所述能夠再利用的固體酸觸媒的情況,相對於所裝入的2,6-位經取代的苯胺系化合物的量,為1 wt%~50 wt%,較佳為5 wt%~40 wt%,更佳為10 wt%~30 wt%。於固體酸的使用量多於所述範圍的情況下,難以確保反應溶液的流動性,於固體酸的使用量少於所述範圍的情況下,反應不會充分進行,或者反應時間變長)。反應可視需要使用甲苯、二甲苯等有機溶劑進行,亦可於無溶劑下進行。例如,於在2,6-位經取代的苯胺系化合物、烷基苯甲醛樹脂及溶劑的混合溶液中添加酸性觸媒後,於觸媒含有水的情況下,藉由共沸將水自系統內去除。然後,於40℃~180℃、較佳為50℃~170℃下進行0.5小時~20小時反應。其後,一邊藉由共沸脫水而除去系統內產生的水或低分子量成分等一邊升溫,於180℃~300℃、較佳為190℃~250℃、更佳為200℃~240℃下進行5小時~50小時、較佳為5小時~20小時反應。反應結束後,利用鹼性水溶液中和酸性觸媒後,向油層加入非水溶性有機溶劑,反覆進行水洗直至廢水變為中性(於使用所述能夠再利用的固體酸觸媒的情況下,藉由過濾而除去觸媒)。
本發明的芳香族胺樹脂的軟化點較佳為80℃以下,更佳為70℃以下。若軟化點高於80℃,則馬來醯亞胺化的樹脂的黏度變高,難以含浸至碳纖維或玻璃纖維中。於增加稀釋溶劑來降低黏度的情況下,於含浸步驟中樹脂有可能無法充分附著於纖維狀材料。
本發明的馬來醯亞胺樹脂是使馬來酸或馬來酸酐於溶劑、觸媒的存在下與本發明的芳香族胺樹脂反應而獲得,例如只要採用日本專利第6429862號公報中記載的方法等即可。該情況下,需要自系統內除去反應中生成的水,因此反應中使用的溶劑使用非水溶性的溶劑。例如可列舉:甲苯、二甲苯等芳香族溶劑;環己烷、正己烷等脂肪族溶劑;二乙醚、二異丙醚等醚類;乙酸乙酯、乙酸丁酯等酯系溶劑;甲基異丁基酮、環戊酮等酮系溶劑等,但並不限定於該些,亦可併用兩種以上。另外,除所述非水溶性溶劑以外,亦可併用非質子性極性溶劑。例如可列舉二甲基碸、二甲基亞碸、二甲基甲醯胺、二甲基乙醯胺、1,3-二甲基-2-咪唑啶酮、N-甲基吡咯啶酮等,亦可併用兩種以上。於使用非質子性極性溶劑的情況下,較佳為使用沸點較所併用的非水溶性溶劑更高者。觸媒並無特別限定,可列舉對甲苯磺酸、羥基-對甲苯磺酸、甲磺酸、硫酸、磷酸等酸性觸媒。例如將馬來酸溶解於甲苯中,於攪拌下添加本發明的芳香族胺樹脂的N-甲基吡咯啶酮溶液,其後加入對甲苯磺酸,一邊於回流條件下自系統內除去生成的水一邊進行反應。
本發明的硬化性樹脂組成物亦可使用公知的任意材料作為本發明的馬來醯亞胺樹脂以外的硬化性樹脂。具體而言,可列舉:酚樹脂、環氧樹脂、胺樹脂、含活性烯烴樹脂、異氰酸酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、氰酸酯樹脂、丙烯基樹脂、甲基丙烯酸樹脂、活性酯樹脂等,就耐熱性、密接性、介電特性的平衡而言,較佳為含有環氧樹脂、含活性烯烴樹脂、氰酸酯樹脂。藉由含有該些硬化性樹脂,可改善硬化物的脆性並且提高對金屬的密接性,可抑制焊料回流時或冷熱循環等可靠性試驗中的封裝的裂紋。本發明的馬來醯亞胺樹脂以外的硬化性樹脂可使用一種,亦可併用多種。
相對於本發明的馬來醯亞胺樹脂,所述硬化性樹脂的使用量通常為小於10質量倍、較佳為小於3質量倍、進而佳為小於2質量倍、特佳為小於1.5質量份的質量範圍。於10質量倍以上的情況下,本發明的馬來醯亞胺樹脂的濃度變低,有可能無法獲得充分的耐熱性或介電特性。另外,較佳的下限值為0.2質量倍以上,進而佳為0.5質量倍以上。
酚樹脂:酚類(苯酚、烷基取代苯酚、芳香族取代苯酚、對苯二酚、間苯二酚、萘酚、烷基取代萘酚、二羥基苯、烷基取代二羥基苯、二羥基萘等)與各種醛(甲醛、乙醛、烷基醛、苯甲醛、烷基取代苯甲醛、羥基苯甲醛、萘醛、戊二醛、鄰苯二甲醛、巴豆醛、肉桂醛(cinnamaldehyde)、糠醛等)的縮聚物;酚類與各種二烯化合物(二環戊二烯、萜烯類、乙烯基環己烯、降冰片二烯、乙烯基降冰片烯、四氫茚、二乙烯基苯、二乙烯基聯苯、二異丙烯基聯苯、丁二烯、異戊二烯等)的聚合物;酚類與酮類(丙酮、甲基乙基酮、甲基異丁基酮、苯乙酮、二苯甲酮等)的縮聚物;藉由酚類與取代聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)、或者取代苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)等的縮聚而獲得的酚樹脂;雙酚類與各種醛的縮聚物;聚苯醚。
環氧樹脂:所述酚樹脂;將醇類等加以縮水甘油基化而得的縮水甘油醚系環氧樹脂;以4-乙烯基-1-環己烯二環氧化物或3,4-環氧環己基甲基-3,4'-環氧環己烷羧酸酯等為代表的脂環式環氧樹脂;以四縮水甘油基二胺基二苯基甲烷(tetraglycidyl diamino diphenylmethane,TGDDM)或三縮水甘油基-對胺基苯酚等為代表的縮水甘油胺系環氧樹脂;縮水甘油酯系環氧樹脂。
胺樹脂:二胺基二苯基甲烷;二胺基二苯基碸;異佛爾酮二胺;萘二胺;苯胺酚醛清漆;鄰乙基苯胺酚醛清漆;藉由苯胺與二氯二甲苯(xylylene chloride)的反應而獲得的苯胺樹脂;藉由日本專利第6429862號公報中記載的苯胺與取代聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)、或者取代苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)的反應而獲得的胺樹脂。
含活性烯烴樹脂:所述酚樹脂與含活性烯烴的鹵素系化合物(氯甲基苯乙烯、氯化烯丙基(allyl chloride)、氯化甲基烯丙基、丙烯醯氯等)的縮聚物;含活性烯烴的酚類(2-烯丙基苯酚、2-丙烯基苯酚、4-烯丙基苯酚、4-丙烯基苯酚、丁香酚(eugenol)、異丁香酚(isoeugenol)等)與鹵素系化合物(4,4'-雙(甲氧基甲基)-1,1'-聯苯、1,4-雙(氯甲基)苯、4,4'-二氟二苯甲酮、4,4'-二氯二苯甲酮、4,4'-二溴二苯甲酮、三聚氯化氰(cyanuric chloride)等)的縮聚物;環氧樹脂或者醇類與經取代或未經取代的丙烯酸酯類(丙烯酸酯、甲基丙烯酸酯等)的縮聚物;馬來醯亞胺樹脂(4,4'-二苯基甲烷雙馬來醯亞胺、聚苯甲烷馬來醯亞胺、間伸苯基雙馬來醯亞胺、2,2'-雙〔4-(4-馬來醯亞胺苯氧基)苯基〕丙烷、3,3'-二甲基-5,5'-二乙基-4,4'-二苯基甲烷雙馬來醯亞胺、4-甲基-1,3-伸苯基雙馬來醯亞胺、4,4'-二苯基醚雙馬來醯亞胺、4,4'-二苯基碸雙馬來醯亞胺、1,3-雙(3-馬來醯亞胺苯氧基)苯、1,3-雙(4-馬來醯亞胺苯氧基)苯)。
異氰酸酯樹脂:對苯二異氰酸酯、間苯二異氰酸酯、對二甲苯二異氰酸酯、間二甲苯二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、4,4'-二苯基甲烷二異氰酸酯、萘二異氰酸酯等的芳香族二異氰酸酯類;異佛爾酮二異氰酸酯、六亞甲基二異氰酸酯、4,4'-二環己基甲烷二異氰酸酯、氫化二甲苯二異氰酸酯、降冰片烯二異氰酸酯、離胺酸二異氰酸酯等脂肪族或脂環結構的二異氰酸酯類;異氰酸酯單體的一種以上的縮二脲體或將所述二異氰酸酯化合物三聚化而成的異氰酸酯體等多異氰酸酯;藉由所述異氰酸酯化合物與多元醇化合物的胺基甲酸酯化反應而獲得的多異氰酸酯。
聚醯胺樹脂:以選自胺基酸(6-胺基己酸、11-胺基十一烷酸、12-胺基十二烷酸、對胺基甲基苯甲酸等)、內醯胺(ε-己內醯胺、ω-十一烷內醯胺、ω-月桂內醯胺)及二胺(乙二胺、三亞甲基二胺、四亞甲基二胺、五亞甲基二胺、六亞甲基二胺、七亞甲基二胺、八亞甲基二胺、九亞甲基二胺、癸二胺、十一烷二胺、十二烷二胺、十三烷二胺、十四烷二胺、十五烷二胺、十六烷二胺、十七烷二胺、十八烷二胺、十九烷二胺、二十烷二胺、2-甲基-1,5-二胺基戊烷、2-甲基-1,8-二胺基辛烷等脂肪族二胺;環己烷二胺、雙-(4-胺基環己基)甲烷、雙(3-甲基-4-胺基環己基)甲烷等脂環式二胺;二甲苯二胺等芳香族二胺等)與二羧酸(草酸、丙二酸、丁二酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十一烷二酸、十二烷二酸等脂肪族二羧酸;對苯二甲酸、間苯二甲酸、2-氯對苯二甲酸、2-甲基對苯二甲酸、5-甲基間苯二甲酸、間苯二甲酸-5-磺酸鈉、六氫對苯二甲酸、六氫間苯二甲酸等芳香族二羧酸;環己烷二羧酸等脂環族二羧酸;該些二羧酸的二烷基酯以及二氯化物)的混合物中的一種以上為主要原料的聚合物。
聚醯亞胺樹脂:所述二胺與四羧酸二酐(4,4'-(六氟亞異丙基)二鄰苯二甲酸酐、5-(2,5-二氧代四氫-3-呋喃基)-3-甲基-環己烯-1,2-二羧酸酐、均苯四甲酸二酐、1,2,3,4-苯四羧酸二酐、3,3',4,4'-二苯甲酮四羧酸二酐、2,2',3,3'-二苯甲酮四羧酸二酐、3,3',4,4'-聯苯基四羧酸二酐、3,3',4,4'-二苯基碸四羧酸二酐、2,2',3,3'-聯苯基四羧酸二酐、亞甲基-4,4'-二鄰苯二甲酸二酐、1,1-亞乙基-4,4'-二鄰苯二甲酸二酐、2,2'-亞丙基-4,4'-二鄰苯二甲酸二酐、1,2-伸乙基-4,4'-二鄰苯二甲酸二酐、1,3-三亞甲基-4,4'-二鄰苯二甲酸二酐、1,4-四亞甲基-4,4'-二鄰苯二甲酸二酐、1,5-五亞甲基-4,4'-二鄰苯二甲酸二酐、4,4'-氧基二鄰苯二甲酸二酐、硫代-4,4'-二鄰苯二甲酸二酐、磺醯基-4,4'-二鄰苯二甲酸二酐、1,3-雙(3,4-二羧基苯基)苯二酐、1,3-雙(3,4-二羧基苯氧基)苯二酐、1,4-雙(3,4-二羧基苯氧基)苯二酐、1,3-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、1,4-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、雙[3-(3,4-二羧基苯氧基)苯基]甲烷二酐、雙[4-(3,4-二羧基苯氧基)苯基]甲烷二酐、2,2-雙[3-(3,4-二羧基苯氧基)苯基]丙烷二酐、2,2-雙[4-(3,4-二羧基苯氧基)苯基]丙烷二酐、雙(3,4-二羧基苯氧基)二甲基矽烷二酐、1,3-雙(3,4-二羧基苯基)-1,1,3,3-四甲基二矽氧烷二酐、2,3,6,7-萘四羧酸二酐、1,4,5,8-萘四羧酸二酐、1,2,5,6-萘四羧酸二酐、3,4,9,10-苝四羧酸二酐、2,3,6,7-蒽四羧酸二酐、1,2,7,8-菲四羧酸二酐、乙烯四羧酸二酐、1,2,3,4-丁烷四羧酸二酐、1,2,3,4-環丁烷四羧酸二酐、環戊烷四羧酸二酐、環己烷-1,2,3,4-四羧酸二酐、環己烷-1,2,4,5-四羧酸二酐、3,3',4,4'-雙環己基四羧酸二酐、羰基-4,4'-雙(環己烷-1,2-二羧酸)二酐、亞甲基-4,4'-雙(環己烷-1,2-二羧酸)二酐、1,2-伸乙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、1,1-亞乙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、2,2-亞丙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、氧基-4,4'-雙(環己烷-1,2-二羧酸)二酐、硫代-4,4'-雙(環己烷-1,2-二羧酸)二酐、磺醯基-4,4'-雙(環己烷-1,2-二羧酸)二酐、雙環[2,2,2]辛-7-烯-2,3,5,6-四羧酸二酐、rel-[1S,5R,6R]-3-氧雜雙環[3,2,1]辛烷-2,4-二酮-6-螺-3'-(四氫呋喃-2',5'-二酮)、4-(2,5-二氧代四氫呋喃-3-基)-1,2,3,4-四氫萘-1,2-二羧酸酐、乙二醇-雙-(3,4-二羧酸酐苯基)醚、4,4'-聯苯基雙(偏苯三酸單酯酸酐)、9,9'-雙(3,4-二羧基苯基)芴二酐)的縮聚物。
氰酸酯樹脂:為藉由使酚樹脂與鹵化氰反應而獲得的氰酸酯化合物,作為具體例,可列舉:二氰氧基苯(dicyanatobenzene)、三氰氧基苯、二氰氧基萘、二氰氧基聯苯、2,2'-雙(4-氰氧基苯基)丙烷、雙(4-氰氧基苯基)甲烷、雙(3,5-二甲基-4-氰氧基苯基)甲烷、2,2'-雙(3,5-二甲基-4-氰氧基苯基)丙烷、2,2'-雙(4-氰氧基苯基)乙烷、2,2'-雙(4-氰氧基苯基)六氟丙烷、雙(4-氰氧基苯基)碸、雙(4-氰氧基苯基)硫醚、苯酚酚醛清漆氰酸酯、將苯酚-二環戊二烯共縮合物的羥基轉換為氰酸酯基者等,但並不限定於該些。
另外,日本專利特開2005-264154號公報中記載有合成方法的氰酸酯化合物由於低吸濕性、阻燃性、介電特性優異,因此作為氰酸酯化合物而言特佳。
為了根據需要使氰酸酯基三聚化而形成均三嗪(sym-triazine)環,氰酸酯樹脂亦可含有環烷酸鋅、環烷酸鈷、環烷酸銅、環烷酸鉛、辛酸鋅、辛酸錫、乙醯丙酮鉛、馬來酸二丁基錫等觸媒。相對於熱硬化性樹脂組成物的合計質量100質量份,觸媒通常使用0.0001質量份~0.10質量份,較佳為使用0.00015質量份~0.0015質量份。
活性酯化合物:可根據需要使用一分子中具有一個以上的活性酯基的化合物作為環氧樹脂等本發明中記載的必須成分以外的硬化性樹脂的硬化劑。作為活性酯系硬化劑,較佳為苯酚酯類、苯硫酚酯類、N-羥基胺酯類、雜環羥基化合物的酯類等於一分子中具有兩個以上的反應活性高的酯基的化合物。該活性酯系硬化劑較佳為藉由羧酸化合物及硫代羧酸化合物中的至少任一種化合物、與羥基化合物及硫醇化合物中的至少任一種化合物的縮合反應而獲得。特別是就耐熱性提高的觀點而言,較佳為由羧酸化合物與羥基化合物獲得的活性酯系硬化劑,較佳為由羧酸化合物與苯酚化合物及萘酚化合物中的至少任一種化合物獲得的活性酯系硬化劑。
作為羧酸化合物,例如可列舉:苯甲酸、乙酸、琥珀酸、馬來酸、衣康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、均苯四甲酸等。
作為苯酚化合物或萘酚化合物,例如可列舉:對苯二酚、間苯二酚、雙酚A、雙酚F、雙酚S、酸式酚酞(phenolphthalin)、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、苯酚、鄰甲酚、間甲酚、對甲酚、兒茶酚、α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘、二羥基二苯甲酮、三羥基二苯甲酮、四羥基二苯甲酮、間苯三酚(phloroglucin)、苯三酚、二環戊二烯型二苯酚化合物、苯酚酚醛清漆等。此處,所謂「二環戊二烯型二苯酚化合物」是指於二環戊二烯一分子中二分子的苯酚縮合而獲得的二苯酚化合物。
作為活性酯系硬化劑的較佳的具體例,可列舉包含二環戊二烯型二苯酚結構的活性酯化合物、包含萘結構的活性酯化合物、包含苯酚酚醛清漆的乙醯基化物的活性酯化合物、包含苯酚酚醛清漆的苯甲醯基化物的活性酯化合物。其中,更佳為包含萘結構的活性酯化合物、包含二環戊二烯型二苯酚結構的活性酯化合物。所謂「二環戊二烯型二苯酚結構」,表示包含伸苯基-二環伸戊基-伸苯基的二價結構單元。
作為活性酯系硬化劑的市售品,例如可列舉:作為包含二環戊二烯型二苯酚結構的活性酯化合物的「EXB9451」、「EXB9460」、「EXB9460S」、「HPC-8000-65T」、「HPC-8000H-65TM」、「EXB-8000L-65TM」、「EXB-8150-65T」(迪愛生(DIC)公司製造);作為包含萘結構的活性酯化合物的「EXB9416-70BK」(迪愛生(DIC)公司製造);作為包含苯酚酚醛清漆的乙醯基化物的活性酯化合物的「DC808」(三菱化學公司製造);作為包含苯酚酚醛清漆的苯甲醯基化物的活性酯化合物的「YLH1026」、「YLH1030」、「YLH1048」(三菱化學公司製造);作為為苯酚酚醛清漆的乙醯基化物的活性酯系硬化劑的「DC808」(三菱化學公司製造);作為含磷原子的活性酯系硬化劑的迪愛生(DIC)公司製造的「EXB-9050L-62M」等。
於本發明的硬化性樹脂組成物中,為了促進馬來醯亞胺樹脂等能夠自由基聚合的硬化性樹脂的自聚合或與其他成分的自由基聚合,較佳為使用自由基聚合起始劑。作為可使用的自由基聚合起始劑,可列舉:過氧化甲基乙基酮、過氧化乙醯丙酮等酮過氧化物類;過氧化苯甲醯等二醯基過氧化物類;二枯基過氧化物、1,3-雙(第三丁基過氧異丙基)苯等二烷基過氧化物類;過氧化苯甲酸第三丁酯、1,1-二-第三丁基過氧化環己烷等過氧化縮酮類;α-枯基過氧化新癸酸酯、第三丁基過氧化新癸酸酯、第三丁基過氧化三甲基乙酸酯、1,1,3,3-四甲基丁基過氧-2-乙基己酸酯、第三戊基過氧-2-乙基己酸酯、第三丁基過氧-2-乙基己酸酯、第三戊基過氧-3,5,5-三甲基己酸酯、第三丁基過氧-3,5,5-三甲基己酸酯、第三戊基過氧苯甲酸酯等烷基過氧酸酯類;二-2-乙基己基過氧化二碳酸酯、雙(4-第三丁基環己基)過氧化二碳酸酯、第三丁基過氧化異丙基碳酸酯、1,6-雙(第三丁基過氧化羰基氧基)己烷等過氧化碳酸酯類;第三丁基過氧化氫、枯烯過氧化氫、第三丁基過氧化辛酸酯、過氧化月桂醯等有機過氧化物或偶氮二異丁腈、4,4'-偶氮雙(4-氰基戊酸)、2,2'-偶氮雙(2,4-二甲基戊腈)等偶氮系化合物等公知的自由基聚合起始劑,但並不特別限定於該些。較佳為酮過氧化物類、二醯基過氧化物類、氫過氧化物類、二烷基過氧化物類、過氧化縮酮類、烷基過氧酸酯類、過氧化碳酸酯類等,更佳為二烷基過氧化物類。作為自由基聚合起始劑的添加量,相對於硬化性樹脂組成物的質量100質量份,較佳為0.01質量份~5質量份,特佳為0.01質量份~3質量份。若所使用的自由基聚合起始劑的量多,則於聚合反應時分子量不能充分增加。
於本發明的硬化性樹脂組成物中,根據需要併用硬化促進劑(硬化觸媒)亦無妨。作為可使用的硬化促進劑的具體例,可列舉:2-(二甲基胺基甲基)苯酚或1,8-二氮雜-雙環(5,4,0)十一烯-7等三級胺類;三苯基膦等膦類;四丁基銨鹽、三異丙基甲基銨鹽、三甲基癸基銨鹽、鯨蠟基三甲基銨鹽、十六烷基三甲基氫氧化銨等四級銨鹽;三苯基苄基鏻鹽、三苯基乙基鏻鹽、四丁基鏻鹽等四級鏻鹽(四級鹽的抗衡離子為鹵素、有機酸根離子、氫氧化物離子等,並無特別指定,特佳為有機酸根離子、氫氧化物離子)、辛酸錫、羧酸鋅(2-乙基己酸鋅、硬脂酸鋅、山萮酸鋅、肉豆蔻酸鋅)或磷酸酯鋅(辛基磷酸鋅、硬脂基磷酸鋅等)等鋅化合物等過渡金屬化合物(過渡金屬鹽)等。相對於環氧樹脂100重量份,硬化促進劑的調配量根據需要可使用0.01重量份~5.0重量份。
於本發明的硬化性樹脂組成物中,亦可含有含磷化合物作為阻燃性賦予成分。作為含磷化合物,可為反應型者亦可為添加型者。作為含磷化合物的具體例,可列舉:三甲基磷酸酯、三乙基磷酸酯、三甲苯基磷酸酯、三 (二甲苯基)磷酸酯、甲苯基二苯基磷酸酯、甲苯基-2,6-二 (二甲苯基)磷酸酯、1,3-伸苯基雙(二 (二甲苯基)磷酸酯)、1,4-伸苯基雙(二 (二甲苯基)磷酸酯)、4,4'-聯苯基(二 (二甲苯基)磷酸酯)等磷酸酯類;9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(2,5-二羥基苯基)-10H-9-氧雜-10-磷雜菲-10-氧化物等磷烷(phosphane)類;使環氧樹脂與所述磷烷類的活性氫反應而獲得的含磷環氧化合物、紅磷等,較佳為磷酸酯類、磷烷類或含磷環氧化合物,特佳為1,3-伸苯基雙(二 (二甲苯基)磷酸酯)、1,4-伸苯基雙(二 (二甲苯基)磷酸酯)、4,4'-聯苯基(二 (二甲苯基)磷酸酯)或含磷環氧化合物。含磷化合物的含量較佳為(含磷化合物)/(全部環氧樹脂)為0.1~0.6(重量比)的範圍。若為0.1以下,則阻燃性不充分,若為0.6以上,則有對硬化物的吸濕性、介電特性造成不良影響之虞。
進而,於本發明的硬化性樹脂組成物中,根據需要亦可添加抗氧化劑。作為可使用的抗氧化劑,可列舉酚系、硫系、磷系抗氧化劑。抗氧化劑可單獨使用或者組合使用兩種以上。相對於本發明的硬化性樹脂組成物中的樹脂成分100重量份,抗氧化劑的使用量通常為0.008重量份~1重量份,較佳為0.01重量份~0.5重量份。該些抗氧化劑可分別單獨使用,亦可將兩種以上組合併用。於本發明中,特佳為磷系的抗氧化劑。
作為酚系抗氧化劑的具體例,可例示:2,6-二-第三丁基-對甲酚、丁基化羥基苯甲醚、2,6-二-第三丁基-對乙基苯酚、硬脂基-β-(3,5-二-第三丁基-4-羥基苯基)丙酸酯、異辛基-3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯、2,4-雙-(正辛硫基)-6-(4-羥基-3,5-二-第三丁基苯胺)-1,3,5-三嗪、2,4-雙[(辛硫基)甲基]-鄰甲酚等單酚類;2,2'-亞甲基雙(4-甲基-6-第三丁基苯酚)、2,2'-亞甲基雙(4-乙基-6-第三丁基苯酚)、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)、4,4'-亞丁基雙(3-甲基-6-第三丁基苯酚)、三乙二醇-雙[3-(3-第三丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己二醇-雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、N,N'-六亞甲基雙(3,5-二-第三丁基-4-羥基-氫化肉桂醯胺)、2,2-硫代-二伸乙基雙[3-(3,5-二-第三丁基-4-羥基苯基)丙酸酯]、3,5-二-第三丁基-4-羥基苄基磷酸酯-二乙基酯、3,9-雙[1,1-二甲基-2-{β-(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基}乙基]2,4,8,10-四氧雜螺[5,5]十一烷、雙(3,5-二-第三丁基-4-羥基苄基磺酸乙酯)鈣等雙酚類;1,1,3-三(2-甲基-4-羥基-5-第三丁基苯基)丁烷、1,3,5-三甲基-2,4,6-三(3,5-二-第三丁基-4-羥基苄基)苯、四[亞甲基-3-(3',5'-二-第三丁基-4'-羥基苯基)丙酸酯]甲烷、雙[3,3'-雙-(4'-羥基-3'-第三丁基苯基)丁酸乙二醇酯、三-(3,5-二-第三丁基-4-羥基苄基)-異氰脲酸酯、1,3,5-三(3',5'-二-第三丁基-4'-羥基苄基)-均三嗪-2,4,6-(1H,3H,5H)三酮、生育酚等高分子型酚類。
作為硫系抗氧化劑的具體例,可例示3,3'-硫代二丙酸二月桂酯、3,3'-硫代二丙酸二肉豆蔻基酯、3,3'-硫代二丙酸二硬脂基酯等。
作為磷系抗氧化劑的具體例,可例示:亞磷酸三苯酯、亞磷酸二苯基異癸基酯、亞磷酸苯基二異癸基酯、亞磷酸三(壬基苯基)酯、亞磷酸季戊四醇二異癸基酯、三(2,4-二-第三丁基苯基)亞磷酸酯、環狀新戊烷四基雙(十八烷基)亞磷酸酯、環狀新戊烷四基雙(2,4-二-第三丁基苯基)亞磷酸酯、環狀新戊烷四基雙(2,4-二-第三丁基-4-甲基苯基)亞磷酸酯、雙[2-第三丁基-6-甲基-4-{2-(十八烷氧基羰基)乙基}苯基]鹵代亞磷酸酯等亞磷酸酯類;9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(3,5-二-第三丁基-4-羥基苄基)-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-癸氧基-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物等氧雜磷雜菲氧化物類等。
進而,於本發明的硬化性樹脂組成物中,根據需要亦可添加光穩定劑。作為光穩定劑,較佳為受阻胺系的光穩定劑,特佳為受阻胺光穩定劑(Hindered Amine Light Stabilizer,HALS)等。作為HALS,並無特別限定,作為具代表性者,可列舉:二丁胺・1,3,5-三嗪・N,N'-雙(2,2,6,6-四甲基-4-哌啶基)-1,6-六亞甲基二胺與N-(2,2,6,6-四甲基-4-哌啶基)丁胺的縮聚物、琥珀酸二甲基-1-(2-羥基乙基)-4-羥基-2,2,6,6-四甲基哌啶縮聚物、聚〔{6-(1,1,3,3-四甲基丁基)胺基-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亞胺基}六亞甲基{(2,2,6,6-四甲基-4-哌啶基)亞胺基}〕、雙(1,2,2,6,6-五甲基-4-哌啶基)〔〔3,5-雙(1,1-二甲基乙基)-4-羥基苯基〕甲基〕丁基丙二酸酯、雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、2-(3,5-二-第三丁基-4-羥基苄基)-2-正丁基丙二酸雙(1,2,2,6,6-五甲基-4-哌啶基)酯等。HALS可僅使用一種,亦可將兩種以上併用。
進而,於本發明的硬化性樹脂組成物中,根據需要亦可調配黏合劑樹脂。作為黏合劑樹脂,可列舉縮丁醛系樹脂、縮醛系樹脂、丙烯酸系樹脂、環氧-尼龍系樹脂、腈基丁二烯橡膠(nitrile butadiene rubber,NBR)-酚系樹脂、環氧-NBR系樹脂、聚醯胺系樹脂、聚醯亞胺系樹脂、矽酮系樹脂等,但並不限定於該些。黏合劑樹脂的調配量較佳為不損及硬化物的阻燃性、耐熱性的範圍,相對於樹脂成分100質量份,根據需要通常使用0.05質量份~50質量份,較佳為0.05質量份~20質量份。
進而,於本發明的硬化性樹脂組成物中,根據需要可添加熔融二氧化矽、結晶二氧化矽、多孔質二氧化矽、氧化鋁、鋯石、矽酸鈣、碳酸鈣、石英粉、碳化矽、氮化矽、氮化硼、氧化鋯、氮化鋁、石墨、鎂橄欖石(forsterite)、塊滑石(steatite)、尖晶石(spinel)、富鋁紅柱石(mullite)、二氧化鈦、滑石(talc)、黏土、氧化鐵、石棉(asbestos)、玻璃粉末等粉體,或將該些製成球狀或破碎狀的無機填充材。另外,特別是於獲得半導體封裝用的硬化性樹脂組成物的情況下,於硬化性樹脂組成物中,所述無機填充材的使用量通常為80質量%~92質量%、較佳為83質量%~90質量%的範圍。
於本發明的硬化性樹脂組成物中,根據需要可調配公知的添加劑。作為可使用的添加劑的具體例,可列舉聚丁二烯及其改質物、丙烯腈共聚物的改質物、聚苯醚、聚苯乙烯、聚乙烯、聚醯亞胺、氟樹脂、矽酮凝膠、矽油、矽烷偶合劑般的填充材的表面處理劑、脫模劑、碳黑、酞青藍、酞青綠等著色劑。相對於硬化性樹脂組成物100質量份,該些添加劑的調配量較佳為1,000質量份以下,更佳為700質量份以下的範圍。
本發明的硬化性樹脂組成物可藉由以規定的比例均勻地混合所述各成分而獲得,通常於130℃~180℃下以30秒~500秒的範圍預硬化,進而於150℃~200℃下後硬化2小時~15小時,藉此進行充分的硬化反應,獲得本發明的硬化物。另外,亦可使硬化性樹脂組成物的成分均勻地分散或溶解於溶劑等中,除去溶媒後使其硬化。
以該方式獲得的本發明的硬化性樹脂組成物具有耐濕性、耐熱性、高接著性。因此,本發明的硬化性樹脂組成物可於要求耐濕性、耐熱性、高接著性的廣泛的領域中使用。具體而言,作為絕緣材料、積層板(印刷配線板、球柵陣列(ball grid array,BGA)用基板、增層基板等)、密封材料、抗蝕劑等所有電氣電子零件用材料有用。另外,除了成形材料、複合材料以外,亦可用於塗料材料、接著劑等領域中。特別是於半導體密封中,耐焊料回流性有益。
半導體裝置具有利用本發明的硬化性樹脂組成物來密封者。作為半導體裝置,例如可列舉:雙列直插式封裝(dual in-line package,DIP)、四面扁平封裝(quad flat package,QFP)、球柵陣列(ball grid array,BGA)、晶片尺寸封裝(chip size package,CSP)、小外形封裝(small outline package,SOP)、薄小外形封裝(thin small outline package,TSOP)、薄四面扁平封裝(thin quad flat package,TQFP)等。
本發明的硬化性樹脂組成物的製備方法並無特別限定,可僅將各成分均勻地混合,或者亦可預聚物化。例如於存在或不存在觸媒的情況下、於存在或不存在溶劑的情況下加熱本發明的硬化性樹脂,藉此進行預聚物化。同樣地,除了本發明的硬化性樹脂以外,亦可追加環氧樹脂、胺化合物、馬來醯亞胺系化合物、氰酸酯化合物、酚樹脂、酸酐化合物等硬化劑及其他添加劑而進行預聚物化。關於各成分的混合或預聚物化,於不存在溶劑的情況下使用例如擠出機、捏合機、輥等,於存在溶劑的情況下使用帶有攪拌裝置的反應釜等。
作為均勻地混合的方法,以於50℃~100℃的範圍內的溫度下,使用捏合機、輥、行星式混合機等裝置融合的方式進行混合,製成均勻的樹脂組成物。所得的樹脂組成物亦可於粉碎後,利用壓錠機(tablet machine)等成型機成型為圓柱的錠狀,或者製成顆粒狀的粉體、或粉狀的成型體,或者將該些組成物於表面支撐體上熔融而成型為厚度0.05 mm~10 mm的片狀,製成硬化性樹脂組成物成型體。所得的成型體成為於0℃~20℃下無黏性的成型體,即使於-25℃~0℃下保管1週以上,流動性、硬化性亦幾乎不降低。
對於所得的成型體,可利用轉注成型機、壓縮成型機而成型為硬化物。
亦可於本發明的硬化性樹脂組成物中添加有機溶劑而製成清漆狀的組成物(以下簡稱為清漆)。根據需要使本發明的硬化性樹脂組成物溶解於甲苯、二甲苯、丙酮、甲基乙基酮、甲基異丁基酮、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等溶劑中製成清漆,含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙等基材中並進行加熱乾燥,對所得的預浸體進行熱壓成形,藉此可製成本發明的硬化性樹脂組成物的硬化物。此時的溶劑使用於本發明的硬化性樹脂組成物與該溶劑的混合物中通常佔10重量%~70重量%、較佳為佔15重量%~70重量%的量。另外,若為液狀組成物,則亦可直接例如藉由樹脂轉注成形(resin transfer molding,RTM)方式獲得含有碳纖維的硬化性樹脂硬化物。
另外,亦可將本發明的硬化性組成物用作膜型組成物的改質劑。具體而言,可於提高B-階段的可撓性等的情況下使用。此種膜型的樹脂組成物是將本發明的硬化性樹脂組成物製成所述硬化性樹脂組成物清漆並塗佈於剝離膜上,於加熱下除去溶劑後,進行B階段化,藉此作為片狀的接著劑而獲得。該片狀接著劑可用作多層基板等的層間絕緣層。
本發明的硬化性樹脂組成物可加熱熔融、低黏度化而含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維等強化纖維中,藉此獲得預浸體。作為其具體例,例如可列舉E玻璃布、D玻璃布、S玻璃布、Q玻璃布、球狀玻璃布、NE玻璃布、及T玻璃布等玻璃纖維,進而可列舉玻璃以外的無機物的纖維或聚對苯二甲醯對苯二胺(polyparaphenylene terephthalamide)(凱夫拉(kevlar)(註冊商標),杜邦(Dupont)股份有限公司製造)、全芳香族聚醯胺、聚酯;以及聚對伸苯基苯並噁唑(polyparaphenylene benzoxazole)、聚醯亞胺及碳纖維等有機纖維,但並不特別限定於該些。作為基材的形狀,並無特別限定,例如可列舉織布、不織布、粗紗(roving)、切股氈(chopped strand mat)等。另外,作為織布的織法,已知有平紋組織、方平組織(basket weave)、斜紋組織(twill weave)等,可自該些公知的織法中根據目標用途或性能適當選擇來使用。另外,較佳為使用對織布進行了開纖處理者或利用矽烷偶合劑等進行了表面處理的玻璃織布。基材的厚度並無特別限定,較佳為0.01 mm~0.4 mm左右。另外,亦可藉由將所述清漆含浸於強化纖維中並進行加熱乾燥而獲得預浸體。
本實施方式的積層板包括一片以上的所述預浸體。積層板只要為包括一片以上的預浸體者則並無特別限定,亦可具有其他的任何層。作為積層板的製造方法,可適當應用一般公知的方法,並無特別限定。例如,於貼有金屬箔的積層板的成形時,可使用多段壓製機、多段真空壓製機、連續成形機、高壓釜成形機等,可藉由將所述預浸體彼此積層並進行加熱加壓成形而獲得積層板。此時,加熱的溫度並無特別限定,較佳為65℃~300℃,更佳為120℃~270℃。另外,加壓的壓力並無特別限定,若加壓過大則積層板的樹脂的固體成分調整困難,品質不穩定,另外若壓力過小,則氣泡或積層間的密接性變差,因此較佳為2.0 MPa~5.0 MPa,更佳為2.5 MPa~4.0 MPa。本實施方式的積層板藉由包括具有金屬箔的層,可較佳地用作後述的貼有金屬箔的積層板。
將所述預浸體裁斷為所期望的形狀,視需要與銅箔等積層後,一邊利用壓製成形法或高壓釜成形法、片捲曲(sheet winding)成形法等對積層物施加壓力,一邊使硬化性樹脂組成物加熱硬化,藉此可獲得電氣電子用積層板(印刷配線板)或碳纖維強化材。
本發明的硬化物可用於成型材料、接著劑、複合材料、塗料等各種用途。本發明記載的硬化性樹脂組成物的硬化物顯示出優異的耐熱性及介電特性,因此可較佳地用於半導體元件用密封材、液晶顯示元件用密封材、有機電致發光(electroluminescence,EL)元件用密封材、印刷配線基板、增層積層板等電氣電子零件或碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度結構材用複合材料中。
[實施例]
接下來,藉由實施例更具體地對本發明進行說明。以下,只要並無特別說明,則份為重量份。再者,本發明並不限定於該些實施例。
以下記載實施例中使用的各種分析方法。
<胺當量>
依據日本工業標準(Japanese Industrial Standards,JIS)K-7236附件A(縮水甘油胺的修正法),將所獲得的值作為胺當量。
<軟化點>
依據JIS K-7234進行測定。
<ICI黏度(150℃)>
依據JIS K-7117-2進行測定。
<重量平均分子量(Mw)>
使用聚苯乙烯標準液,藉由聚苯乙烯換算進行計算。
凝膠滲透層析儀(gel permeation chromatograph,GPC):DGU-20A3R、LC-20AD、SIL-20AHT、RID-20A、SPD-20A、CTO-20A、CBM-20A(均為島津製作所製造)
管柱:索得克斯(Shodex)KF-603、KF-602×2、KF-601×2
連結溶離液:四氫呋喃
流速:0.5 ml/min.
管柱溫度:40℃
檢測器:RI(折射率(refractive index))(示差折射檢測器)
[實施例1]
向安裝有溫度計、冷卻管、迪安斯塔克(Dean-Stark)共沸蒸餾捕集器、攪拌機的燒瓶中裝入二甲苯甲醛樹脂(尼卡諾(NIKANOL)G,福道(Fudow)股份有限公司製造)198份、2-乙基-6-甲基苯胺(東京化成公司製造)622份及甲苯300份、活性白土(日本活性白土公司製造)82份,於120℃下反應1小時後,一邊提取餾出物一邊升溫至150℃,並保持4小時。其後,升溫至200℃,於200℃下進行10小時反應。放冷後,利用甲苯300份進行稀釋,藉由過濾而除去活性白土後,於加熱減壓下蒸餾除去溶劑及過剩的2-乙基-6-甲基苯胺,藉此獲得芳香族胺樹脂(A1)315份(軟化點:65℃,熔融黏度為0.13 Pa·s,胺當量:199 g/eq,Mw:581)。將所獲得的胺樹脂的1H-NМR圖表示於圖1中。
1H-NMR(400 MHz,二甲基亞碸(dimethylsulfoxide,DMSO)-d6):δ(ppm)0.92-1.18 (m, 221H), 1.88-2.46 (m, 611H), 3.48-3.98 (m, 124H), 4.21-4.38 (m, 127H), 5.33 (s, 4H), 6.30-6.70 (m, 156H), 6.82-7.02 (m, 35H), 7.23 (s, 4H)
[實施例2]
向安裝有溫度計、冷卻管、迪安斯塔克共沸蒸餾捕集器、攪拌機的燒瓶中裝入馬來酸酐(東京化成公司製造)221份及甲苯100份,將進行加熱而共沸的水及甲苯冷卻、分液後,僅將作為有機層的甲苯返回至系統內進行脫水。接著,將實施例1中獲得的芳香族胺樹脂(A1)300份溶解於N-甲基-2-吡咯啶酮50份與甲苯150份的混合溶劑中獲得樹脂溶液,一邊將系統內保持為80℃~85℃,一邊歷時1小時滴加所得的樹脂溶液。滴加結束後,於相同溫度下進行2小時反應,加入對甲苯磺酸6份,於回流條件下將共沸的縮合水及甲苯冷卻、分液後,僅將作為有機層的甲苯返回至系統內進行脫水,同時進行20小時反應。反應結束後,追加甲苯600份,反覆水洗而除去對甲苯磺酸及過剩的馬來酸酐,進行加熱而藉由共沸將水自系統內去除。繼而,濃縮反應溶液,獲得含有70重量%的馬來醯亞胺樹脂(M1)的樹脂溶液。馬來醯亞胺樹脂(M1)的重量平均分子量(Mw)為827。將藉由減壓濃縮而以固體形式取出馬來醯亞胺樹脂(M1)者(M1')的1H-NМR圖表示於圖2中。
1H-NMR(400 MHz,DMSO-d6):δ(ppm)0.80-1.10 (m, 7H), 1.75-2.40 (m, 20H), 3.61-4.28 (m, 4H), 6.59-7.18 (m, 6H), 7.25 (d, 4H)
[比較例1]
向安裝有溫度計、冷卻管、迪安斯塔克共沸蒸餾捕集器、攪拌機的燒瓶中裝入二甲苯甲醛樹脂(尼卡諾(NIKANOL)G,福道(Fudow)股份有限公司製造)210份、苯胺(東京化成公司製造)738份及甲苯100份、活性白土95份,於120℃下反應1小時後,一邊提取餾出物一邊升溫至150℃,並保持4小時。其後,升溫至200℃,於200℃下進行10小時反應。放冷後,利用甲苯300份進行稀釋,藉由過濾而除去活性白土(日本活性白土公司製造)後,於加熱減壓下蒸餾除去溶劑及過剩的苯胺,藉此獲得芳香族胺樹脂(A2)314份(軟化點:66.6℃,熔融黏度為0.23 Pa·s,胺當量:198 g/eq,Mw:734)。
[比較例2]
向安裝有溫度計、冷卻管、迪安斯塔克共沸蒸餾捕集器、攪拌機的燒瓶中裝入馬來酸酐(東京化成公司製造)186份及甲苯250份,將進行加熱而共沸的水及甲苯冷卻、分液後,僅將作為有機層的甲苯返回至系統內進行脫水。接著,將比較例1中獲得的芳香族胺樹脂(A2)250份溶解於N-甲基-2-吡咯啶酮250份與甲苯250份的混合溶劑中獲得樹脂溶液,一邊將系統內保持為80℃~85℃,一邊歷時1小時滴加所得的樹脂溶液。滴加結束後,於相同溫度下進行2小時反應,加入對甲苯磺酸(東京化成公司製造)5份,於回流條件下將共沸的縮合水及甲苯冷卻、分液後,僅將作為有機層的甲苯返回至系統內進行脫水,同時進行20小時反應。反應結束後,追加甲苯500份,實施水洗,結果於分液時分離為三層,無法萃取。
[比較例3]
進行與比較例2同樣的反應,反應結束後,追加甲苯3000份、N-甲基-2-吡咯啶酮300份,反覆水洗而除去對甲苯磺酸及過剩的馬來酸酐,進行加熱而藉由共沸將水自系統內去除。繼而,濃縮反應溶液,獲得含有70重量%的馬來醯亞胺樹脂(M2)的樹脂溶液。馬來醯亞胺樹脂(M2)的重量平均分子量(Mw)為1204。
確認到與比較例2中獲得的芳香族胺樹脂(A2)相比較,實施例1中獲得的芳香族胺樹脂(A1)的重量平均分子量小,分子量分佈尖銳。芳香族胺樹脂(A2)的重量平均分子量超過700,因此由芳香族胺樹脂(A2)所獲得的馬來醯亞胺樹脂(M2)由於其分子量的大小及極性的高低,於比較例2所示的通常的水洗中難以精製,且無法去除酸觸媒等雜質。馬來醯亞胺樹脂(M2)如比較例3所示,使用大量的有機溶劑,若不進而併用高極性高沸點溶劑則無法水洗。因此,存在馬來醯亞胺樹脂中殘留高沸點溶劑的問題,就產業廢棄物的減少、同一設備中的獲得量的提高、生產步驟的簡易化等觀點而言,可以說芳香族胺樹脂(A1)優異。
[實施例3、比較例4、比較例5]
以表1的比例(質量份)調配實施例2中獲得的藉由減壓濃縮而以固體形式取出馬來醯亞胺化合物(M1)者(M1')、BMI-2300:苯胺酚醛清漆型馬來醯亞胺化合物(大和化成工業公司製造)、聯苯芳烷基型環氧樹脂(NC-3000-L,日本化藥股份有限公司製造)、聯苯芳烷基型酚樹脂(卡亞哈得(KAYAHARD)GPH-65,日本化藥股份有限公司製造)、作為硬化促進劑的2E4MZ(2-乙基-4-甲基咪唑,四國化成公司製造),於金屬容器中加熱熔融混合,直接流入模具中,於220℃下硬化2小時。
[實施例4]
以表1的比例(質量份)調配實施例2中獲得的藉由減壓濃縮而以固體形式取出馬來醯亞胺化合物(M1)者(M1')及二枯基過氧化物(化藥阿克蘇(Kayaku Akzo)公司製造),於金屬容器中加熱熔融混合,直接流入模具中,於220℃下硬化2小時。
將對以該方式獲得的硬化物的物性測定下述項目而得的結果示於表1中。
<耐熱性試驗>
・玻璃轉移溫度:藉由動態黏彈性試驗機進行測定,tanδ為最大值時的溫度。
動態黏彈性測定器:TA儀器(TA-instruments)製造的DMA-2980
升溫速度:2℃/分鐘
<介電常數試驗及介電損耗正切試驗>
・使用關東電子應用開發(股)製造的1 GHz空腔共振器,利用空腔共振器攝動法進行測試。其中,以樣品尺寸為寬1.7 mm×長100 mm、厚度為1.7 mm進行試驗。
[表1]
M1':實施例2中記載的於加熱減壓下蒸餾除去溶劑而以固體形式取出馬來醯亞胺樹脂者
BMI-2300:苯胺酚醛清漆型馬來醯亞胺化合物(大和化成工業公司製造)
DCP:二枯基過氧化物(化藥阿克蘇公司製造)
NC-3000-L:聯苯芳烷基型環氧樹脂(日本化藥公司製造)
GPH-65:聯苯芳烷基型酚樹脂(日本化藥公司製造)
2E4MZ:2-乙基-4-甲基咪唑(四國化成公司製造)
調配量 | 實施例3 | 實施例4 | 比較例4 | 比較例5 | |
馬來醯亞胺化合物 | M1' | 100 | 100 | ||
BMI-2300 | 100 | ||||
自由基聚合起始劑 | DCP | 0.5 | 0.5 | ||
環氧樹脂 | NC-3000-L | 44 | 48 | ||
酚硬化劑 | GPH-65 | 32 | 35 | ||
咪唑 | 2E4MZ | 2 | 1.2 | ||
評價試驗結果 | |||||
玻璃轉移溫度 | ℃ | 248 | 350以上 | 141 | 350以上 |
介電常數 | % | 2.8 | 2.6 | 3.1 | 3.0 |
介電損耗正切 | 0.007 | 0.003 | 0.018 | 0.005 |
由表1確認到,實施例3、實施例4具有高的耐熱性,且具有優異的介電特性。
[產業上之可利用性]
本發明的硬化性樹脂組成物於以電氣電子零件用絕緣材料(高可靠性半導體密封材料等)及積層板(印刷配線板、BGA用基板、增層基板等)、接著劑(導電性接著劑等)或碳纖維強化塑膠(carbon fiber reinforced plastic,CFRP)為代表的各種複合材料用、塗料等用途中有用。
無
圖1表示實施例1的1H-核磁共振(nuclear magnetic resonance,NMR)圖表。
圖2表示實施例2的1H-NMR圖表。
Claims (10)
- 如請求項1所述的馬來醯亞胺樹脂,其中所述式(1)所表示的芳香族胺樹脂是由2,6-位進行了取代的苯胺系化合物與烷基苯甲醛樹脂反應而獲得的芳香族胺樹脂。
- 如請求項1所述的馬來醯亞胺樹脂,其中所述式(1)所表示的芳香族胺樹脂的軟化點為80℃以下。
- 如請求項1所述的馬來醯亞胺樹脂,其中所述式(1)所表示的芳香族胺樹脂的重量平均分子量為300~700。
- 如請求項5所述的馬來醯亞胺樹脂,其中所述式(2)所表示的芳香族胺樹脂是由2-乙基-6-甲基苯胺與二甲苯甲醛樹脂反應而獲得的芳香族胺樹脂。
- 如請求項5所述的馬來醯亞胺樹脂,其中所述式(2)所表示的芳香族胺樹脂的軟化點為80℃以下。
- 如請求項5所述的馬來醯亞胺樹脂,其中所述式(2)所表示的芳香族胺樹脂的重量平均分子量為300~700。
- 一種硬化性樹脂組成物,含有如請求項1至請求項8中任一項所述的馬來醯亞胺樹脂。
- 一種硬化物,其是將如請求項9所述的硬化性樹脂組成物硬化而獲得。
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