JP2020176190A - マレイミド樹脂、硬化性樹脂組成物およびその硬化物 - Google Patents
マレイミド樹脂、硬化性樹脂組成物およびその硬化物 Download PDFInfo
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- JP2020176190A JP2020176190A JP2019078503A JP2019078503A JP2020176190A JP 2020176190 A JP2020176190 A JP 2020176190A JP 2019078503 A JP2019078503 A JP 2019078503A JP 2019078503 A JP2019078503 A JP 2019078503A JP 2020176190 A JP2020176190 A JP 2020176190A
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- 229920005989 resin Polymers 0.000 title claims abstract description 104
- 239000011347 resin Substances 0.000 title claims abstract description 104
- 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 34
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 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 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 15
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 9
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 24
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- 239000003795 chemical substances by application Substances 0.000 description 12
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- 239000011574 phosphorus Substances 0.000 description 11
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000011973 solid acid Substances 0.000 description 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 7
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- 239000004305 biphenyl Substances 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
- 239000004744 fabric Substances 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 239000002184 metal Substances 0.000 description 6
- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000004996 alkyl benzenes 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
- 150000001412 amines Chemical class 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
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- 239000000843 powder Substances 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
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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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Epoxy Resins (AREA)
- Pyrrole Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
[1]
下記式(1)で表されるマレイミド樹脂。
[2]
下記式(2)で表される芳香族アミン樹脂と、マレイン酸またはマレイン酸無水物とを反応させることにより得られる前項[1]に記載のマレイミド樹脂。
[3]
前記式(1)のRがメチル基である前項[1]または[2]に記載のマレイミド樹脂。
[4]
下記式(3)で表される前項[1]乃至[3]に記載のマレイミド樹脂。
[5]
前項[1]乃至[4]のいずれか一項に記載のマレイミド樹脂を含有する硬化性樹脂組成物。
[6]
前項[5]に記載の硬化性樹脂組成物を硬化して得られる硬化物。
本発明のマレイミド樹脂は下記式(1)で表される。
本発明の芳香族アミン樹脂は、下記式(3)で表されるときが特に好ましい。
上記硬化性樹脂の使用量は、本発明のマレイミド樹脂に対して、通常10質量倍未満、好ましくは3質量倍未満、さらに好ましくは2質量倍未満、特に好ましくは1.5質量部未満の質量範囲である。10質量倍以上の場合、本発明のマレイミド樹脂の濃度が低くなり、十分な耐熱性や誘電特性が得られなくなる可能性がある。また、好ましい下限値は0.2質量倍以上、さらに好ましくは0.5質量倍以上である。
また、特開2005−264154号公報に合成方法が記載されているシアネートエステル化合物は、低吸湿性、難燃性、誘電特性に優れているためシアネートエステル化合物として特に好ましい。
シアネート樹脂は、必要に応じてシアネート基を三量化させてsym−トリアジン環を形成するために、ナフテン酸亜鉛、ナフテン酸コバルト、ナフテン酸銅、ナフテン酸鉛、オクチル酸亜鉛、オクチル酸錫、鉛アセチルアセトナート、ジブチル錫マレエート等の触媒を含有させることもできる。
カルボン酸化合物としては、例えば、安息香酸、酢酸、コハク酸、マレイン酸、イタコン酸、フタル酸、イソフタル酸、テレフタル酸、ピロメリット酸等が挙げられる。
フェノール化合物又はナフトール化合物としては、例えば、ハイドロキノン、レゾルシン、ビスフェノールA、ビスフェノールF、ビスフェノールS、フェノールフタリン、メチル化ビスフェノールA、メチル化ビスフェノールF、メチル化ビスフェノールS、フェノール、o−クレゾール、m−クレゾール、p−クレゾール、カテコール、α−ナフトール、β−ナフトール、1,5−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、2,6−ジヒドロキシナフタレン、ジヒドロキシベンゾフェノン、トリヒドロキシベンゾフェノン、テトラヒドロキシベンゾフェノン、フロログルシン、ベンゼントリオール、ジシクロペンタジエン型ジフェノール化合物、フェノールノボラック等が挙げられる。ここで、「ジシクロペンタジエン型ジフェノール化合物」とは、ジシクロペンタジエン1分子にフェノール2分子が縮合して得られるジフェノール化合物をいう。
活性エステル系硬化剤の好ましい具体例としては、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物、ナフタレン構造を含む活性エステル化合物、フェノールノボラックのアセチル化物を含む活性エステル化合物、フェノールノボラックのベンゾイル化物を含む活性エステル化合物が挙げられる。中でも、ナフタレン構造を含む活性エステル化合物、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物がより好ましい。「ジシクロペンタジエン型ジフェノール構造」とは、フェニレン−ジシクロペンチレン−フェニレンからなる2価の構造単位を表す。
活性エステル系硬化剤の市販品としては、例えば、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物として、「EXB9451」、「EXB9460」、「EXB9460S」、「HPC−8000−65T」、「HPC−8000H−65TM」、「EXB−8000L−65TM」、「EXB−8150−65T」(DIC社製);ナフタレン構造を含む活性エステル化合物として「EXB9416−70BK」(DIC社製);フェノールノボラックのアセチル化物を含む活性エステル化合物として「DC808」(三菱化学社製);フェノールノボラックのベンゾイル化物を含む活性エステル化合物として「YLH1026」、「YLH1030」、「YLH1048」(三菱化学社製);フェノールノボラックのアセチル化物である活性エステル系硬化剤として「DC808」(三菱化学社製);リン原子含有活性エステル系硬化剤としてDIC社製の「EXB−9050L−62M」;等が挙げられる。
得られた成型体についてトランスファー成型機、コンプレッション成型機にて硬化物に成型することができる。
上記プリプレグを所望の形に裁断、必要により銅箔などと積層後、積層物にプレス成形法やオートクレーブ成形法、シートワインディング成形法などで圧力をかけながら硬化性樹脂組成物を加熱硬化させることにより電気電子用積層板(プリント配線板)や、炭素繊維強化材を得ることができる。
以下に実施例で用いた各種分析方法について記載する。
<アミン当量>
JIS K−7236 付属書A(グリシジルアミンの補正法)に準拠し、得られた値をアミン当量とした。
<軟化点>
JIS K−7234に準拠して測定。
<ICI粘度(150℃)>
JIS K−7117−2に準拠して測定。
<重量平均分子量(Mw)>
ポリスチレン標準液を用いてポリスチレン換算により算出した。
GPC:DGU−20A3R,LC−20AD,SIL−20AHT,RID−20A,SPD−20A,CTO−20A,CBM−20A(いずれも島津製作所製)
カラム:Shodex KF−603、KF−602x2、KF−601x2)
連結溶離液:テトラヒドロフラン
流速:0.5ml/min.
カラム温度:40℃
検出:RI(示差屈折検出器)
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコにキシレンホルマリン樹脂(ニカノールG フドー株式会社製)210部、アニリン(東京化成社製)738部とトルエン100部、活性白土95部を仕込み、120℃で1時間反応後、留出物を抜き出しながら150℃まで昇温し、4時間保持した。その後、200℃まで昇温し、200℃で10時間反応を行った。放冷後、トルエン300部で希釈し、濾過で活性白土(日本活性白土社製)を除去後、加熱減圧下において溶剤および過剰のアニリンを留去することにより芳香族アミン樹脂(A1)314部を得た(軟化点:66.6℃、溶融粘度は0.23Pa・s、アミン当量:198g/eq、Mw:734)。
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコに無水マレイン酸(東京化成社製)186部とトルエン250部を仕込み、加熱して共沸してくる水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行った。次に、合成例1で得られた芳香族アミン樹脂(A1)250部をN−メチル−2−ピロリドン250部とトルエン250部の混合溶剤に溶解した樹脂溶液を、系内を80〜85℃に保ちながら1時間かけて滴下した。滴下終了後、同温度で2時間反応を行い、pートルエンスルホン酸(東京化成社製)5部を加えて、還流条件で共沸してくる縮合水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行いながら20時間反応を行った。反応終了後、トルエン3000部、N−メチル−2−ピロリドン300部を追加し、水洗を繰り返してpートルエンスルホン酸及び過剰の無水マレイン酸を除去し、加熱して共沸により水を系内から除いた。次いで反応溶液を濃縮して、マレイミド樹脂(M1)を70重量%含有する樹脂溶液を得た。M1の重量平均分子量(Mw)は1204であった。マレイミド樹脂(M1)を減圧濃縮により固体として取り出ししたもの(M1’)の1H−NМRチャートを図2に示す。
1H−NMR(400MHz,DMSO−d6);δ(ppm)1.64−2.33(m,83H),2.70(s,6H),3.30(t,2H),3.40−4.10(m,31H),6.43−7.40(m,109H)
実施例1で得られたマレイミド化合物(M1)を減圧濃縮により固体として取り出ししたもの(M1’)、ビフェニルアラルキル型マレイミド樹脂(MIR−3000、日本化薬株式会社製)、ビフェニルアラルキル型エポキシ樹脂(NC−3000−L 日本化薬株式会社製)、ビフェニルアラルキル型フェノール樹脂(KAYAHARD GPH−65 日本化薬株式会社製)、硬化促進剤として2E4MZ(2−エチル−4−メチルイミダゾール 四国化成社製)を表1の割合(質量部)で配合し、金属容器中で加熱溶融混合してそのまま金型に流し込み、220℃で2時間硬化させた。
・ガラス転移温度:動的粘弾性試験機により測定し、tanδが最大値のときの温度。
動的粘弾性測定器:TA−instruments製DMA−2980
昇温速度:2℃/分
<誘電率試験・誘電正接試験>
・(株)関東電子応用開発製の1GHz空洞共振器を用いて、空洞共振器摂動法にてテストを行った。ただし、サンプルサイズは幅1.7mm×長さ100mmとし、厚さは1.7mmで試験を行った。
MIR−3000:ビフェニルアラルキル型マレイミド樹脂(日本化薬社製)
NC−3000−L:ビフェニルアラルキル型エポキシ樹脂(日本化薬社製)
GPH−65:ビフェニルアラルキル型フェノール樹脂(日本化薬社製)
2E−4MZ:2−メチル−4−イミダゾール(四国化成社製)
Claims (6)
- 下記式(1)で表されるマレイミド樹脂。
- 下記式(2)で表される芳香族アミン樹脂と、マレイン酸またはマレイン酸無水物とを反応させることにより得られる請求項1に記載のマレイミド樹脂。
(式(2)中、Rは炭素数1〜18の炭化水素基を表す。mは1〜4の整数を表し、nは平均値であり、1≦n≦20を表す。) - 前記式(1)のRがメチル基である請求項1または2に記載のマレイミド樹脂。
- 下記式(3)で表される請求項1乃至3に記載のマレイミド樹脂。
- 請求項1乃至4のいずれか一項に記載のマレイミド樹脂を含有する硬化性樹脂組成物。
- 請求項5に記載の硬化性樹脂組成物を硬化して得られる硬化物。
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TW109112559A TWI829914B (zh) | 2019-04-17 | 2020-04-15 | 馬來醯亞胺樹脂、硬化性樹脂組成物及其硬化物 |
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CN202080007550.XA CN113227047A (zh) | 2019-04-17 | 2020-04-15 | 马来酰亚胺树脂、硬化性树脂组合物及其硬化物 |
KR1020217024163A KR20220004617A (ko) | 2019-04-17 | 2020-04-15 | 말레이미드 수지, 경화성 수지 조성물 및 그 경화물 |
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KR20240002167A (ko) | 2022-06-28 | 2024-01-04 | 디아이씨 가부시끼가이샤 | 폴리말레이미드 수지, 경화성 조성물, 경화물, 프리프레그, 회로 기판, 빌드업 필름, 반도체 봉지재 및 반도체 장치 |
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