WO2023026923A1 - Composition de résine durcissable, produit durci, matériau composite durcissable, matériau composite durci, vernis pour matériaux de carte de circuit imprimé, corps multicouche, feuille métallique avec résine, composant électrique/électronique, et matériau de carte de circuit imprimé - Google Patents
Composition de résine durcissable, produit durci, matériau composite durcissable, matériau composite durci, vernis pour matériaux de carte de circuit imprimé, corps multicouche, feuille métallique avec résine, composant électrique/électronique, et matériau de carte de circuit imprimé Download PDFInfo
- Publication number
- WO2023026923A1 WO2023026923A1 PCT/JP2022/031080 JP2022031080W WO2023026923A1 WO 2023026923 A1 WO2023026923 A1 WO 2023026923A1 JP 2022031080 W JP2022031080 W JP 2022031080W WO 2023026923 A1 WO2023026923 A1 WO 2023026923A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- resin composition
- resins
- curable resin
- vinylbenzyl
- Prior art date
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- -1 multilayer body Substances 0.000 title claims abstract description 173
- 239000011342 resin composition Substances 0.000 title claims abstract description 68
- 229920005989 resin Polymers 0.000 title claims description 76
- 239000011347 resin Substances 0.000 title claims description 76
- 239000002131 composite material Substances 0.000 title claims description 33
- 239000011888 foil Substances 0.000 title claims description 25
- 229910052751 metal Inorganic materials 0.000 title claims description 25
- 239000002184 metal Substances 0.000 title claims description 25
- 239000000463 material Substances 0.000 title claims description 22
- 239000002966 varnish Substances 0.000 title claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
- 239000011256 inorganic filler Substances 0.000 claims abstract description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007870 radical polymerization initiator Substances 0.000 claims description 9
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 8
- 229910052582 BN Inorganic materials 0.000 claims description 7
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000003063 flame retardant Substances 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 6
- 229920006305 unsaturated polyester Polymers 0.000 claims description 6
- 239000013034 phenoxy resin Substances 0.000 claims description 5
- 229920006287 phenoxy resin Polymers 0.000 claims description 5
- 229920001721 polyimide Polymers 0.000 claims description 5
- 239000009719 polyimide resin Substances 0.000 claims description 5
- 229920001955 polyphenylene ether Polymers 0.000 claims description 5
- 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 4
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 4
- 239000004962 Polyamide-imide Substances 0.000 claims description 4
- 239000004695 Polyether sulfone Substances 0.000 claims description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 4
- 229920002492 poly(sulfone) Polymers 0.000 claims description 4
- 229920003050 poly-cycloolefin Polymers 0.000 claims description 4
- 229920002312 polyamide-imide Polymers 0.000 claims description 4
- 229920005668 polycarbonate resin Polymers 0.000 claims description 4
- 239000004431 polycarbonate resin Substances 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 4
- 239000004645 polyester resin Substances 0.000 claims description 4
- 229920006393 polyether sulfone Polymers 0.000 claims description 4
- 229920002530 polyetherether ketone Polymers 0.000 claims description 4
- 239000004697 Polyetherimide Substances 0.000 claims description 3
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 claims description 3
- 229920001601 polyetherimide Polymers 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 31
- 238000001723 curing Methods 0.000 description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- 239000000835 fiber Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
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- 229920002554 vinyl polymer Polymers 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 14
- 229920001568 phenolic resin Polymers 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002245 particle Substances 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical class C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 10
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000006087 Silane Coupling Agent Substances 0.000 description 9
- 239000007822 coupling agent Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000004744 fabric Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 6
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 5
- 229920000049 Carbon (fiber) Polymers 0.000 description 5
- 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 5
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- 239000011248 coating agent Substances 0.000 description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 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
- 150000002989 phenols Chemical class 0.000 description 5
- 239000012783 reinforcing fiber Substances 0.000 description 5
- 229920006337 unsaturated polyester resin Polymers 0.000 description 5
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000004760 aramid Substances 0.000 description 4
- 229920003235 aromatic polyamide Polymers 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- 238000001035 drying Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000003475 lamination Methods 0.000 description 4
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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- 125000005650 substituted phenylene group Chemical group 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RGYRCSKRQNNKOE-UHFFFAOYSA-N 1-phenylacenaphthylene Chemical class C=12C3=CC=CC2=CC=CC=1C=C3C1=CC=CC=C1 RGYRCSKRQNNKOE-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- 230000000052 comparative effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
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- 239000001095 magnesium carbonate Substances 0.000 description 3
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 3
- 235000014380 magnesium carbonate Nutrition 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 3
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- 125000005504 styryl group Chemical group 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- WFCJSNUJPWSKNE-UHFFFAOYSA-N 1-(bromomethyl)-3-ethenylbenzene Chemical compound BrCC1=CC=CC(C=C)=C1 WFCJSNUJPWSKNE-UHFFFAOYSA-N 0.000 description 2
- VTPQLJUADNBKRM-UHFFFAOYSA-N 1-(bromomethyl)-4-ethenylbenzene Chemical compound BrCC1=CC=C(C=C)C=C1 VTPQLJUADNBKRM-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002633 Kraton (polymer) Polymers 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001240 acenaphthylenes Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 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
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 2
- 229910002113 barium titanate Inorganic materials 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XPEMYYBBHOILIJ-UHFFFAOYSA-N trimethyl(trimethylsilylperoxy)silane Chemical compound C[Si](C)(C)OO[Si](C)(C)C XPEMYYBBHOILIJ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
- C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—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 an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
Definitions
- the present invention is used as an insulating material for electrical and electronic parts including highly reliable semiconductor encapsulation, various composite materials including laminates (printed wiring boards) and CFRP (carbon fiber reinforced plastic), or molding raw materials.
- the present invention relates to a curable resin composition containing a useful poly(vinylbenzyl) ether compound and its cured product, a curable composite material and its cured product, a laminate comprising its cured product and a metal foil, a resin-coated metal foil, and the like.
- curable resins have been widely used for adhesion, casting, coating, impregnation, lamination, molding compounds, etc.
- its applications have been diversified, and depending on the usage environment and usage conditions, there are cases where conventionally known curable resins cannot be used.
- laminates used in various electric devices are required to have high performance such as high heat resistance with the recent progress of electronic devices.
- curable resins with excellent electrical properties such as a low dielectric constant and a low dielectric loss tangent have been demanded due to the demand for higher computing speeds and propagation speeds in computers and higher frequencies in mobile communication devices.
- Matrix resins for laminates currently in practical use include phenolic resins, epoxy resins, unsaturated polyester resins, vinyl ester resins, and polyimide resins. Although they satisfy the requirements (Patent Documents 1 to 3), they do not fully satisfy the low dielectric constant and low dielectric loss tangent. Vinyl benzyl ether compounds are described in Patent Documents 4 to 6 as solutions to such problems, but the dielectric properties of the cured products described in these Patent Documents are sufficient to meet the performance currently required. It has not been achieved. Patent Document 7 describes a resin structure that further improves dielectric properties, but the thermal conductivity of the described cured product does not sufficiently achieve the performance currently required.
- the present invention provides a cured product exhibiting heat resistance, flame retardancy, low coefficient of thermal expansion, and high thermal conductivity while having the same low dielectric constant and low dielectric loss tangent as those of conventional curable resin compositions.
- Insulating materials for electrical and electronic parts such as semiconductor encapsulation that require high reliability, various composite materials such as laminates (printed wiring boards) and CFRP (carbon fiber reinforced plastic), and raw materials for molding
- the present inventors have found a curable resin composition containing a poly(vinylbenzyl) ether compound having a specific structure and an inorganic filler. The inventors have found that a resin composition can solve the above problems, and completed the present invention.
- the present invention (A) A poly(vinylbenzyl) ether compound represented by the following formula (1), wherein 90% or more of the substitution positions of the vinyl groups in the vinylbenzyl moiety are para positions. ) an ether compound, and (B) an inorganic filler.
- Each R 1 independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a vinylbenzyl group . 60 to 99.9 mol %.
- R 2 independently represents an alkyl group having 1 to 6 carbon atoms, an allyl group, or an aryl group having 6 to 12 carbon atoms.
- R 3 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- Ar 1 and Ar 2 independently represent an aromatic ring group having 6 to 50 carbon atoms.
- n ranges from 1 to 20 on average.
- m is an integer from 0 to 6
- r is an integer from 1 to 3 and m+r does not exceed eight.
- k is 0 or 1;
- the above curable resin composition may further contain one or more components selected from the following components (C) to (F).
- the component (B) is preferably 30 to 750 parts by mass per 100 parts by mass of the component (A).
- the component (B) is preferably at least one selected from the group consisting of boron nitride, silica, alumina, and anhydrous magnesium carbonate.
- the above component (C) is preferably at least one selected from the group consisting of acryloyl compounds, methacryloyl compounds, maleimide compounds, unsaturated polyester resins, allyl compounds, acenaphthylene compounds, isocyanurate compounds and aromatic vinyl compounds.
- the component (D) includes polysulfone resin, polyethersulfone resin, polyphenylene ether resin, phenoxy resin, polycycloolefin resin, hydrogenated styrene-butadiene copolymer, hydrogenated styrene-isoprene copolymer, polyimide resin, and polyamideimide. More preferably, it is at least one selected from the group consisting of resins, polyetherimide resins, polycarbonate resins, polyetheretherketone resins, and polyester resins.
- the present invention also provides a varnish for circuit board materials, which is obtained by dissolving the above curable resin composition in a solvent. Furthermore, the present invention is a cured product obtained by curing the curable resin composition. The present invention also provides a curable composite material comprising the curable resin composition and a substrate, or a cured composite material obtained by curing the same.
- the present invention also provides a laminate having a layer of the composite material cured product and a metal foil layer. Further, the present invention is a resin-coated metal foil having a film formed from the curable resin composition on one side of the metal foil. The present invention also provides an electrical/electronic component or circuit board material using the cured product.
- the curable resin composition of the present invention has the same low dielectric constant and low dielectric loss tangent as compared to conventional curable resin compositions, but also has heat resistance, flame retardancy, low coefficient of thermal expansion, and high thermal conductivity. Gives an excellent cured product.
- the poly(vinylbenzyl) ether compound used as component (A) in the present invention is a compound having a structure represented by general formula (1).
- R 1 independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a vinylbenzyl group.
- the proportion (mol %) of vinylbenzyl groups in all R 1 is 60 to 99.9 mol %.
- the proportion (mol %) of vinylbenzyl groups is preferably 70 to 99 mol %, more preferably 75 to 95 mol %. If the proportion of vinylbenzyl groups is less than 60 mol %, insufficient curing and deterioration of dielectric properties may occur due to a small number of polymerization active sites.
- the proportion (mol %) of alkyl groups in all R 1 is 0.1 to 40 mol %.
- the proportion of alkyl groups is preferably 1 to 30 mol %, more preferably 2 to 30 mol %, still more preferably 3 to 30 mol %.
- Hydrogen atoms may be present, but the hydroxyl group ratio, which represents the ratio (mol%) of hydrogen atoms in all R 1 , is preferably 10 mol% or less, more preferably 5 mol% or less. If there are many hydrogen atoms, the dielectric properties may deteriorate.
- 90% or more of the vinyl groups are at the para position to the methylene groups of the benzyl group, preferably 92% or more, more preferably 95% or more are at the para position.
- the alkyl group having 1 to 12 carbon atoms may be linear, branched or cyclic, and may be a so-called aralkyl group having an aromatic group as a substituent.
- aralkyl group having an aromatic group For example, methyl group, ethyl group, n-propyl group, isopropyl group, allyl group, propargyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, t- pentyl group, cyclopentyl group, n-hexyl group, isohexyl group, cyclohexyl group, n-heptyl group, cycloheptyl group, methylcyclohexyl group, n-octyl group, cyclooctyl group, n-nonyl group, 3,3,5- tri
- branched or cyclic alkyl groups tend to provide higher heat resistance than linear alkyl groups.
- the number of carbon atoms is preferably 1 to 4 in the case of a chain alkyl group, and 6 in the case of a cyclic alkyl group.
- Preferred are methyl group, ethyl group, n-propyl group, isopropyl group, isobutyl group, t-butyl group and cyclohexyl group, more preferred are methyl group, ethyl group, n-propyl group and t-butyl group, A cyclohexyl group, more preferably a methyl group.
- a vinylbenzyl group is represented by CH 2 ⁇ CH—Ar 3 —CH 2 —.
- Ar 3 is a phenylene group or a substituted phenylene group.
- Substituents for the substituted phenylene group include, for example, an alkyl group, an alkoxy group, and a phenyl group.
- An alkyl group having 1 to 6 carbon atoms is preferred.
- Ar 3 is more preferably an unsubstituted, alkyl group-substituted, alkoxy group-substituted, or phenyl group-substituted phenylene group.
- r is the substitution number of one OR group and represents an integer of 1 to 3, preferably 1 or 2 from the viewpoint of solubility and toughness.
- the substituent R 2 of Ar 1 independently represents an alkyl group having 1 to 6 carbon atoms, an allyl group, or an aryl group having 6 to 12 carbon atoms.
- the aryl group may further have a substituent such as an alkyl group having 1 to 6 carbon atoms.
- it is preferably a hydrogen atom (R 2 is unsubstituted), an alkyl group having 1 to 6 carbon atoms, or 6 to 12 carbon atoms (more preferably is an aryl group having 6 carbon atoms, particularly preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
- m is the number of substituents R 2 of Ar 1 and represents an integer of 0-6.
- m is preferably 1 or 2 from the viewpoint of the balance between solubility and flame retardancy.
- m+r is 8 or less, preferably 1-4.
- the alkyl group having 1 to 6 carbon atoms represents a linear, branched or cyclic alkyl group. Examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, t-butyl group, pentyl group, hexyl group and cyclohexyl group.
- branched or cyclic alkyl groups tend to provide higher heat resistance than linear alkyl groups.
- the number of carbon atoms is preferably 1 to 4 in the case of a chain alkyl group, and 6 in the case of a cyclic alkyl group. From the viewpoint of improving heat resistance, isopropyl group, isobutyl group, t-butyl group and cyclohexyl group are preferred, and t-butyl group and cyclohexyl group are more preferred.
- a methyl group is also preferred because it tends to improve flame retardancy.
- R 3 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
- alkyl group having 1 to 6 carbon atoms are the same as those for R 2 above, and the preferred groups are also the same.
- Ar 1 represents an aromatic ring group having 6 to 50 carbon atoms.
- it is an aromatic ring group selected from a benzene ring, a naphthalene ring, a biphenyl ring, or a biphenyl structure, and has a structure obtained by removing two hydroxyl groups from an aromatic diol compound.
- Ar 1 is preferably a naphthalene ring or a biphenyl ring, more preferably a naphthalene ring.
- aromatic diol compounds include hydroquinone, resorcinol, dihydroxybenzenes such as catechol, dihydroxynaphthalenes, biphenol, bisphenol A, bisphenolacetophenone, bisphenol AF, bisphenol AD, bisphenol B, bisphenol BP, bisphenol C, Bisphenols such as bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenoltrimethylcyclohexane, bisphenolcyclohexane, bisphenolcyclododecane, bisphenolfluorene, oxybisphenol and thiobisphenol.
- hydroquinone resorcinol
- dihydroxybenzenes such as catechol, dihydroxynaphthalenes, biphenol, bisphenol A, bisphenolacetophenone, bisphenol AF, bisphenol AD, bisphenol B, bisphenol BP, bisphenol C, Bisphenols such as bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P
- Ar 2 represents an aromatic ring group having 6 to 50 carbon atoms.
- aromatic rings (Ph, Np, and Flu) further have, as substituents, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, It may have 6 to 12 aryloxy groups, 7 to 12 carbon aralky
- the total number of carbon atoms is 6-50, more preferably 6-20.
- Ph represents a phenylene group (--C 6 H 4 --)
- Np represents a naphthylene group (--C 10 H 6 --)
- Flu represents a fluorenyl group (--C 13 H 8 --).
- Ar 2 is more preferably unsubstituted, alkyl group-substituted, alkoxy group-substituted or phenyl group-substituted -Ph-, -Ph-Ph- (biphenylene group) or -Np-, more preferably unsubstituted, -Ph- or -Ph-Ph- substituted with an alkyl group, an alkoxy group, or a phenyl group.
- the alkyl group or alkoxy group having 1 to 6 carbon atoms as the Ar 2 substituent may be linear, branched or cyclic.
- the aryl group or aryloxy group having 6 to 12 carbon atoms for the Ar 2 substituent includes a phenyl group, a tolyl group, an ethylphenyl group, a xylyl group, a propylphenyl group, a trimethylphenyl group, a naphthyl group, an indanyl group, a phenoxy group, Tolyloxy group, ethylphenoxy group, xylyloxy group, propylphenoxy group, trimethylphenoxy group, naphthyloxy group and the like.
- the aralkyl group or aralkyloxy group having 7 to 12 carbon atoms as the Ar 2 substituent includes a benzyl group, a methylbenzyl group, a dimethylbenzyl group, a trimethylbenzyl group, a phenethyl group, a 1-phenylethyl group, a 2-phenylisopropyl group, naphthylmethyl group, benzyloxy group, methylbenzyloxy group, dimethylbenzyloxy group, trimethylbenzyloxy group, phenethyloxy group, 1-phenylethyloxy group, 2-phenylisopropyloxy group, naphthylmethyloxy group and the like.
- k is 0 or 1, preferably 1; n represents an average value of 1 to 20, preferably 1 to 10, more preferably 1 to 5, and particularly preferably 1.0 to 3.0. If n exceeds 20, the viscosity increases, and there is a possibility that the fillability into the fine pattern decreases. In addition, when it has molecular weight distribution, it is a number average value.
- the poly(vinylbenzyl) ether compound (resin) of the present invention preferably has a number average molecular weight (Mn) of 1100 or less, more preferably 1000 or less.
- the poly(vinylbenzyl) ether compound (resin) has a peak area derived from the vinyl aromatic halomethyl compound as a production raw material, and the peak area of the poly(vinylbenzyl) ether compound is 1.0% or less is preferable, 0.5% or less is more preferable, and 0.2% or less is still more preferable with respect to the total peak area. If the residual amount of the vinyl aromatic halomethyl compound is large, there is a possibility that the deterioration of the dielectric properties becomes large after being subjected to a heat history of 250° C. or higher for a long period of time.
- the peak area of the poly(vinylbenzyl) ether compound means the peak area based on the pure poly(vinylbenzyl) ether compound.
- the poly(vinylbenzyl) ether compound (resin) preferably has a residual hydroxyl group content of 120 ppm or less, more preferably 70 ppm or less, derived from the phenolic resin (polyhydric hydroxy resin) represented by the formula (2) of the raw material for production. be.
- the poly(vinylbenzyl)ether compound of the present invention is a reaction product or a purified product thereof and contains minor amounts of other components in addition to the pure poly(vinylbenzyl)ether compound.
- the poly(vinylbenzyl) ether compound is preferably obtained by reacting a phenol resin (polyhydric hydroxy resin) represented by the following formula (2) with a vinyl aromatic halomethyl compound.
- R 2 , R 3 , Ar 1 , Ar 2 , n, m, r, and k are R 2 , R 3 , Ar 1 , Ar 2 , n, m, and Synonymous with r and k.
- R 4 above independently represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
- the ratio (mol%) of alkyl groups in all R 4 is 0.1 to 40 mol%, preferably 1 to 30 mol%, more preferably 3 to 25 mol%, the balance being hydrogen atoms .
- the method for producing the phenolic resin (polyhydric hydroxy resin) represented by formula (2) is not particularly limited. 11-255868, JP-A-11-228673, JP-A-08-073570, JP-A-08-048755, JP-A-10-310634 and JP-A-11-116647, etc. Alternatively, it can be obtained by subjecting phenols and a condensing agent to a condensation reaction, and then removing unreacted phenols and impurities.
- some of the phenolic hydroxyl groups of the phenolic resin represented by formula (2) are, for example, mixed with alcohols having 1 to 12 carbon atoms in the presence of an acidic catalyst. By reacting, an alkyl group having 1 to 12 carbon atoms can be introduced at R 4 of formula (2) and alkoxylated.
- the reaction of introducing an alkyl group and alkoxylating it may be performed before or after the reaction with the vinyl aromatic halomethyl compound, but preferably before the reaction in order to avoid polymerization of the vinyl group. .
- a partially alkoxylated phenolic resin (partially modified phenolic resin) in which some of the hydrogen atoms of hydroxyl groups are substituted with alkyl groups is first synthesized, and then reacted with a vinyl aromatic halomethyl compound to partially A method for obtaining an alkoxylated poly(vinylbenzyl) ether compound.
- the phenolic resin and the vinyl aromatic halomethyl compound are reacted to obtain a poly(vinylbenzyl) ether compound, and then some of the remaining hydroxyl groups are alkylated to obtain a partially alkoxylated poly It is a method for obtaining a (vinylbenzyl) ether compound.
- the raw materials for the phenolic resin polyhydric hydroxy resin
- the phenolic resin may be a mixture of one in which all hydroxyl groups are alkoxylated and one in which all hydroxyl groups remain.
- the hydroxyl group equivalent weight (g/eq.) of the phenolic resin is preferably 200-400, more preferably 220-350.
- a vinyl aromatic halomethyl compound is represented by CH 2 ⁇ CH—Ar 3 —CH 2 X.
- Ar 3 is a phenylene group or a substituted phenylene group.
- Substituents for the substituted phenylene group include, for example, an alkyl group, an alkoxy group, and a phenyl group.
- An alkyl group having 1 to 6 carbon atoms is preferred.
- Ar 3 is more preferably an unsubstituted, alkyl group-substituted, alkoxy group-substituted, or phenyl group-substituted phenylene group.
- X is a halogen atom, preferably a chlorine atom or a bromine atom.
- Preferred vinyl aromatic halomethyl compounds include, for example, p-vinylbenzyl chloride, m-vinylbenzyl chloride, a mixture of p-vinylbenzyl chloride and m-vinylbenzyl chloride, p-vinylbenzyl bromide and m-vinylbenzyl bromide. , a mixture of p-vinylbenzyl bromide and m-vinylbenzyl bromide. Among them, at least one selected from the group consisting of p-vinylbenzyl chloride and m-vinylbenzyl chloride is preferred.
- the use of p-vinylbenzyl chloride improves the structural symmetry and makes it possible to obtain a poly(vinylbenzyl) ether compound that gives a cured product exhibiting high thermal conductivity and high heat resistance. Also, when a mixture of p-vinylbenzyl chloride and m-vinylbenzyl chloride is used, a poly(vinylbenzyl) ether compound with excellent solubility is obtained, and compatibility with other materials and workability are good. Become. It may also contain an o-vinyl aromatic halomethyl compound (o-form). Therefore, the composition ratio of the p-vinyl aromatic halomethyl compound (p-form) is preferably 90 to 100 mol%, more preferably 91 to 99 mol%, and even more preferably 92 to 98 mol%.
- the amount of the vinyl aromatic halomethyl compound to be used can be adjusted as appropriate. ⁇ 1.10 mol is more preferred. When the amount used is within a more preferable range, an amount close to the total amount of the charged phenolic resin reacts with the vinyl aromatic halomethyl compound, the phenolic hydroxyl groups in the phenolic resin are vinylbenzyl etherified, and most of them remain in the reactant. It is preferable because the curing reaction to be performed later proceeds sufficiently and good dielectric properties are exhibited. However, when used in combination with other thermosetting resins, etc., the charged molar ratio may be appropriately adjusted to allow phenolic hydroxyl groups to remain.
- the resulting reaction product is a crude poly(vinylbenzyl) ether compound containing the poly(vinylbenzyl) ether compound of formula (1).
- the amount of the vinyl aromatic halomethyl compound used may be adjusted, or other means such as a poor solvent may be used for reprecipitation purification. Alternatively, unreacted raw materials and the like may be removed by purification by recrystallization.
- the poor solvent those having low solubility for poly(vinylbenzyl) ether compounds and high solubility for halogen compounds are suitable.
- Specific examples of such poor solvents include methanol, ethanol, isopropanol, ethylene glycol, water, and mixed solvents thereof, preferably mixed solvents of water and alcohols.
- a suitable poor solvent is a polar solvent with a solubility parameter of 10 or more, more preferably a polar solvent with a solubility parameter of 11 or more.
- the value of the solubility parameter is most preferably in the range of 15 to 20 from the viewpoint of the recovery yield of the poly(vinylbenzyl) ether compound and the purification efficiency for reducing the residual vinyl aromatic halomethyl compound.
- Component (B) includes boron nitride, silica, alumina, anhydrous magnesium carbonate, barium sulfate, talc, kureni, mica powder, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, and boric acid. At least one selected from aluminum, barium titanate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, barium zirconate, calcium zirconate, and the like. Among these, boron nitride, silica, anhydrous magnesium carbonate, alumina, and the like are preferable.
- Examples of boron nitride include, but are not particularly limited to, a hexagonal normal-pressure phase (h-BN) and a cubic high-pressure phase (c-BN).
- Examples of silica include pulverized silica and silica particles, with silica particles being preferred, but not particularly limited.
- Magnesium carbonate is preferably anhydrous magnesium carbonate (synthetic magnesite), but is not particularly limited.
- inorganic high dielectric powder such as barium titanate and inorganic magnetic material such as ferrite, it is useful as a material for electronic parts, especially as a material for high frequency electronic parts.
- the average particle size of component (B) is not particularly limited, it is preferably 0.5 to 10 ⁇ m, more preferably 1 to 8 ⁇ m, and even more preferably 2 to 5 ⁇ m. If the average particle size is too small, there is a tendency that the thermal conductivity and heat resistance of the obtained cured product cannot be sufficiently improved. If the average particle size is too large, the moldability of the resulting curable resin composition is lowered. If the average particle diameter is too small, when the curable resin composition of the present invention is used as a resin varnish, the viscosity of the varnish tends to increase and the handleability tends to deteriorate.
- the average particle size can be measured by a laser diffraction/scattering method based on Mie scattering theory.
- the particle size distribution of the component (B) is prepared on a volume basis using a laser diffraction particle size distribution analyzer, and the median diameter thereof can be used as the average particle diameter for measurement.
- the measurement sample one obtained by ultrasonically dispersing the component (B) in water can be preferably used.
- a laser diffraction particle size distribution analyzer for example, LA-500 manufactured by HORIBA, Ltd. can be used.
- the component (B) is preferably surface-treated with a surface treatment agent such as an epoxysilane coupling agent, an aminosilane coupling agent, or a titanate-based coupling agent.
- a surface treatment agent such as an epoxysilane coupling agent, an aminosilane coupling agent, or a titanate-based coupling agent.
- Silane coupling agents include, for example, silane coupling agents having at least one functional group selected from the group consisting of vinyl groups, styryl groups, methacryloyl groups, acryloyl groups, and phenylamino groups. That is, this silane coupling agent has at least one of a vinyl group, a styryl group, a methacryloyl group, an acryloyl group, and a phenylamino group as a reactive functional group. Examples thereof include compounds having a hydrolyzable group.
- Silane coupling agents having a vinyl group include, for example, vinyltriethoxysilane and vinyltrimethoxysilane.
- Silane coupling agents having a styryl group include, for example, p-styryltrimethoxysilane and p-styryltriethoxysilane.
- Silane coupling agents having a methacryloyl group include, for example, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldi ethoxysilane, 3-methacryloxypropylethyldiethoxysilane, and the like.
- Silane coupling agents having an acryloyl group include, for example, 3-acryloxypropyltrimethoxysilane and 3-acryloxypropyltriethoxysilane.
- Silane coupling agents having a phenylamino group include, for example, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane.
- the amount of component (B) is 30 to 750 parts by mass, preferably 30 to 500 parts by mass, more preferably 50 to 400 parts by mass, based on 100 parts by mass of component (A). It is preferably 150 to 300 parts by mass. If the blending amount is too small, the effect of blending may not be sufficiently exhibited, and if the blending amount is too large, the cured product tends to become brittle and the peel strength tends to decrease.
- the curable resin composition of the present invention may contain a curing agent as the component (C) within a range that does not impair the effects of the present invention.
- the curing agent of component (C) is a compound having a functional group copolymerizable with component (A), and is not particularly limited, and may be used alone or in combination of two or more.
- Component (C) is at least one selected from the group consisting of acryloyl compounds, methacryloyl compounds, maleimide compounds, unsaturated polyester compounds, allyl compounds, acenaphthylene compounds, isocyanurate compounds and aromatic vinyl compounds.
- the blending ratio is preferably 1 to 80 parts by mass, more preferably 10 to 70 parts by mass, and even more preferably 20 to 60 parts by mass with respect to 100 parts by mass of component (A). .
- Acryloyl compounds include monofunctional acrylate compounds having one acryloyl group in the molecule and polyfunctional acrylate compounds having two or more acryloyl groups in the molecule.
- monofunctional acrylate compounds include ethyl acrylate, propyl acrylate, and butyl acrylate.
- polyfunctional acrylate compounds include diacrylate compounds such as tricyclodecane dimethanol diacrylate, ethylene glycol diacrylate, dipropylene glycol diacrylate, polydipropylene glycol diacrylate, glycerin diacrylate, trimethylolpropane triacrylate, Examples include polyacrylate compounds such as pentaerythritol triacrylate, pentaerythritol tetraacrylate, and dipentaerythritol hexaacrylate, and epoxy acrylate resins obtained by adding an acrylic group to an epoxy resin.
- Methacryloyl compounds include monofunctional methacrylate compounds having one methacryloyl group in the molecule and polyfunctional methacrylate compounds having two or more methacryloyl groups in the molecule.
- monofunctional methacrylate compounds include methyl methacrylate, ethyl methacrylate, propyl methacrylate, and butyl methacrylate.
- polyfunctional methacrylate compounds include dimethacrylate compounds such as tricyclodecane dimethanol dimethacrylate, ethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, polydipropylene glycol dimethacrylate, glycerin dimethacrylate, trimethylolpropane trimethacrylate, penta
- dimethacrylate compounds such as tricyclodecane dimethanol dimethacrylate, ethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, polydipropylene glycol dimethacrylate, glycerin dimethacrylate, trimethylolpropane trimethacrylate
- penta include polymethacrylate compounds such as erythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate, and epoxy methacrylate resins obtained by adding methacryl
- maleimide compounds include monofunctional maleimide compounds having one maleimide group in the molecule, polyfunctional maleimide compounds having two or more maleimide groups in the molecule, and modified maleimide compounds.
- monofunctional maleimide compounds include N-ethylmaleimide, N-cyclohexylmaleimide, N-(2,6-diethylphenyl)maleimide and the like.
- Polyfunctional maleimide compounds include, for example, 4,4'-diphenylmethanebismaleimide, N,N'-hexamethylenebismaleimide, N,N'-ethylenebismaleimide, N,N'-(1,2-phenylene)bis Maleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'-(1,4-phenylene)bismaleimide, N,N'-(4-methyl-1,3-phenylene)bismaleimide and other bismaleimide compounds.
- Modified maleimide compounds include, for example, a modified maleimide compound in which a portion of the molecule is modified with an amine compound, a modified maleimide compound in which a portion of the molecule is modified with a silicone compound, and a portion of the molecule that is an amine compound and Examples include modified maleimide compounds modified with silicone compounds.
- unsaturated polyester compounds include vinyl group-containing unsaturated polyesters, and unsaturated polyesters produced by a polycondensation reaction of polyhydric alcohols and unsaturated polycarboxylic acids can be used.
- Polyhydric alcohol components include, for example, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, 1,3-butylene glycol, 2,3-butylene glycol, 1,6-hexanediol, 2-ethyl- 1,3-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, glycerin, pentaerythritol, bisphenol/alkylene oxide adducts and the like.
- a polyhydric alcohol may be used individually and may use 2 or more types together.
- unsaturated polycarboxylic acids include maleic anhydride, maleic acid, itaconic anhydride, itaconic acid, fumaric acid, and endomethylenetetrahydrophthalic anhydride.
- the unsaturated polycarboxylic acids may be used alone or in combination of two or more.
- a saturated polycarboxylic acid can also be used together with an unsaturated polycarboxylic acid.
- saturated polycarboxylic acids include phthalic anhydride, phthalic acid, terephthalic acid, isophthalic acid, tetrahydrophthalic acid, tetrahydrophthalic anhydride, succinic acid, citraconic acid, adipic acid, and sebacic acid.
- Saturated carboxylic acids may be used alone or in combination of two or more.
- Mw of the unsaturated polyester resin is preferably 6,000 to 35,000, more preferably 6,000 to 20,000, still more preferably 8,000 to 15,000.
- the degree of unsaturation (mol %) of the unsaturated polyester resin is preferably 50-100, more preferably 60-100, still more preferably 70-100. When the degree of unsaturation is within the preferred range, the moldability of the curable resin composition is better.
- allyl compounds include monofunctional allyl compounds having one allyl group in the molecule and polyfunctional allyl compounds having two or more allyl groups in the molecule.
- polyfunctional allyl compounds include triallyl isocyanurate compounds such as triallyl isocyanurate (TAIC), diallyl bisphenol compounds, and diallyl phthalate (DAP).
- TAIC triallyl isocyanurate
- DAP diallyl phthalate
- Acenaphthylene compounds include, for example, acenaphthylene, alkylacenaphthylenes, halogenated acenaphthylenes, and phenylacenaphthylenes.
- alkylacenaphthylenes include 1-methylacenaphthylene, 3-methylacenaphthylene, 4-methylacenaphthylene, 5-methylacenaphthylene, 1-ethylacenaphthylene and 3-ethylacenaphthylene.
- rene 4-ethylacenaphthylene, 5-ethylacenaphthylene and the like.
- halogenated acenaphthylenes include 1-chloroacenaphthylene, 3-chloroacenaphthylene, 4-chloroacenaphthylene, 5-chloroacenaphthylene, 1-bromoacenaphthylene, and 3-bromoacenaphthylene. , 4-bromoacenaphthylene, 5-bromoacenaphthylene and the like.
- Phenylacenaphthylenes include, for example, 1-phenylacenaphthylene, 3-phenylacenaphthylene, 4-phenylacenaphthylene, 5-phenylacenaphthylene and the like.
- the acenaphthylene compound may be a monofunctional acenaphthylene compound having one acenaphthylene structure in the molecule, or a polyfunctional acenaphthylene compound having two or more acenaphthylene structures in the molecule.
- isocyanurate compounds include compounds further having an alkenyl group in the molecule (alkenyl isocyanurate compounds), and examples thereof include triallyl isocyanurate compounds such as triallyl isocyanurate (TAIC).
- alkenyl isocyanurate compounds examples thereof include triallyl isocyanurate compounds such as triallyl isocyanurate (TAIC).
- TAIC triallyl isocyanurate
- aromatic vinyl compounds include monofunctional aromatic vinyl compounds having one vinyl group in the molecule and polyfunctional aromatic vinyl compounds having two or more vinyl groups in the molecule.
- monofunctional aromatic vinyl compounds include styrene, nuclear alkyl-substituted monovinyl aromatic compounds, ⁇ -alkyl-substituted monovinyl aromatic compounds, ⁇ -alkyl-substituted styrenes, alkoxy-substituted styrenes, etc., but are limited to these.
- styrene, ethylvinylbenzene (both m- and p-isomers) and vinylbiphenyl (including each isomer) are particularly preferred from the viewpoint of cost and availability.
- polyfunctional aromatic vinyl compounds include divinylbenzene (both m- and p-isomers), divinylbiphenyl (including various isomers), divinylnaphthalene (including various isomers), and diisopropenylbenzene.
- the curing agent may be used alone or in combination of two or more.
- the curing agent is preferably an allyl compound, and the allyl compound is preferably an allyl isocyanurate compound having two or more allyl groups in the molecule, more preferably triallyl isocyanurate (TAIC).
- TAIC triallyl isocyanurate
- the curable resin composition of the present invention may optionally contain a high molecular weight resin having an Mw of 5,000 or more as component (D).
- Mw must be 5,000 or more.
- the structure is not particularly limited, and either thermosetting or thermoplastic may be used, and only one type may be used, or two or more types may be used in combination.
- component (D) is used, the amount used is about 0.01 to 90 parts by mass, preferably 10 to 50 parts by mass, per 100 parts by mass of components (A) and (C). is.
- thermosetting resins include epoxy resins and phenol resins.
- thermoplastic resins include polyphenylene sulfide resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyvinyl acetal resins, polyimide resins, polyamideimide resins, polybenzoxazole resins, phenoxy resins, Styrenic resins, (meth)acrylic resins, polycyclopentadiene resins, polycycloolefin resins, polyetheretherketone resins, polyetherketone resins, or known thermoplastic elastomers such as styrene-ethylene-propylene copolymers , styrene-ethylene-butylene copolymers, styrene-butadiene copolymers, styrene-isoprene copolymers, hydrogenated styrene-butadiene cop
- polysulfone resin preferably polysulfone resin, polyethersulfone resin, polyphenylene ether resin, phenoxy resin, polycycloolefin resin, hydrogenated styrene-butadiene copolymer, hydrogenated
- examples include styrene-isoprene copolymers, polyimide resins, polyamideimide resins, polyetherimide resins, polycarbonate resins, polyetheretherketone resins, and polyester resins.
- the preferred lower limit of the glass transition temperature (Tg) of component (D) is -40°C, the more preferred lower limit is 50°C, and the most preferred lower limit is 90°C.
- a preferred upper limit is 250°C, and a more preferred upper limit is 200°C.
- the term "cast film/sheet” as used herein refers to a varnish obtained by dissolving the curable resin composition of the present invention in a solvent, and forming a film of this varnish to a thickness of several ⁇ m to several mm. , and dried to form a film or sheet of the curable resin composition.
- the preferred lower limit of Mw of the component (D) is 5,000, the more preferred lower limit is 7,000, the preferred upper limit is 1,000,000, and the more preferred upper limit is 250,000.
- Mw satisfies the preferred lower limit the insulating sheet is less prone to thermal deterioration.
- Mw satisfies the preferred upper limit the compatibility between component (D) and other resin components is enhanced. As a result, it is possible to further improve the handleability of the uncured cast film/sheet and the heat resistance of the cured product of the cast film/sheet.
- the curable resin composition of the present invention may optionally contain a radical polymerization initiator (also referred to as a radical polymerization catalyst) as component (E).
- a radical polymerization initiator also referred to as a radical polymerization catalyst
- the curable resin composition of the present invention is cured by causing a crosslinking reaction by means of heating or the like.
- a radical polymerization initiator may also be included for use.
- radical polymerization initiators include benzoyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, 2,5-dimethyl-2,5-di( t-butylperoxy)hexyne-3, di-t-butylperoxide, t-butylcumylperoxide, ⁇ , ⁇ '-bis(t-butylperoxy-m-isopropyl)benzene, 2,5-dimethyl- 2,5-di(t-butylperoxy)hexane, dicumyl peroxide, di-t-butylperoxyisophthalate, t-butylperoxybenzoate, 2,2-bis(t-butylperoxy)butane, Peroxides such as 2,2-bis(t-butylperoxy)octane, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, di
- the radical polymerization initiator (E) When the radical polymerization initiator (E) is used, its amount is in the range of 0.01 to 10 parts by mass with respect to the total of 100 parts by mass of the components (A) and (C). The reaction proceeds satisfactorily without inhibiting It is preferably 0.05 to 9 parts by mass, more preferably 0.1 to 8 parts by mass, and still more preferably 0.5 to 5 parts by mass.
- a curing accelerator may be used in combination with the radical polymerization initiator.
- curing accelerators that can be used in combination include imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, and 2-ethyl-4-methylimidazole, 2-(dimethylaminomethyl)phenol, and triethylenediamine.
- imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, and 2-ethyl-4-methylimidazole, 2-(dimethylaminomethyl)phenol, and triethylenediamine.
- triethanolamine tertiary amines such as 1,8-diazabicyclo (5,4,0) undecene-7
- organic phosphines such as triphenylphosphine, diphenylphosphine and tributylphosphine, and tin octylate.
- tetrasubstituted phosphonium/tetrasubstituted borate such as tetraphenylphosphonium/tetraphenylborate, tetraphenylphosphonium/ethyltriphenylborate, 2-ethyl-4-methylimidazole/tetraphenylborate, N-methylmorpholine/tetra Tetraphenyl boron salts such as phenyl borate and the like are included.
- a curing accelerator it is used in an amount of 0.01 to 15 parts by mass with respect to a total of 100 parts by mass of components (A) and (C).
- the curable resin composition of the present invention may optionally contain a flame retardant as component (F).
- Component (F) includes, for example, organic phosphorus flame retardants, organic nitrogen-containing phosphorus compounds, nitrogen compounds, silicone flame retardants, metal hydroxides, and bromine compounds.
- organic phosphorus flame retardants include phenanthrene-type phosphorus compounds such as HCA, HCA-HQ and HCA-NQ manufactured by Sanko Co., Ltd., and phosphorus-containing benzoxazine compounds such as HFB-2006M manufactured by Showa Polymer Co., Ltd.
- Leophos 30, 50, 65, 90, 110 manufactured by Ajinomoto Fine Techno Co., Ltd., TPP, RPD, BAPP, CPD, TCP, TXP, TBP, TOP, KP140, TIBP, PPQ manufactured by Hokko Chemical Industry Co., Ltd., OP930 manufactured by Clariant Co., Ltd.
- Phosphate ester compounds such as PX-200 manufactured by Daihachi Chemical Industry Co., Ltd.
- Phosphorus-containing epoxy resins such as FX-289 and FX-305 manufactured by Nippon Steel Chemical & Materials Co., Ltd.
- phosphorus-containing phenoxy resins such as ERF-001 manufactured by Nippon Steel Chemical & Materials Co., Ltd.
- phosphorus-containing epoxy resins such as YL7613 manufactured by Mitsubishi Chemical Corporation.
- organic nitrogen-containing phosphorus compounds include phosphate estermide compounds such as SP670 and SP703 manufactured by Shikoku Kasei Co., Ltd., SPB100 and SPE100 manufactured by Otsuka Chemical Co., Ltd., and FP-series manufactured by Fushimi Seisakusho Co., Ltd.
- phosphazene compounds such as
- metal hydroxides include magnesium hydroxide such as UD65, UD650, and UD653 manufactured by Ube Materials Co., Ltd., and B-30, B-325, B-315, and B-308 manufactured by Tomoe Kogyo Co. , B-303, and UFH-20.
- brominated compounds include ethylenedipentabromobenzene, ethylenebistetrabromoimide, decabromodiphenyloxide, tetradecabromodiphenoxybenzene, ethylenebis(pentabromophenyl), bis(tribromophenoxy)ethane, and the like. be done.
- the blending amount is preferably in the range of 10 to 400 parts by mass with respect to 100 parts by mass of the resin component [(A)+(C)+(D)]. It is more preferably 10 to 100 parts by mass, still more preferably 10 to 50 parts by mass.
- the component (F) By containing the component (F), it can be used particularly effectively as an electrical or electronic component material that requires flame retardancy, especially as a semiconductor encapsulating material or a varnish for circuit boards.
- Hydroquinone, benzoquinone, copper salts, etc. can be added as stabilizers to adjust the degree of hardening.
- Various compounding agents such as stabilizers, release agents, pigments, and reinforcing fibers can be added to the curable resin composition of the present invention, if necessary.
- reinforcing fibers include, but are not limited to, fibers such as glass fibers, carbon fibers, aromatic polyamide fibers, silicon carbide fibers, and alumina fibers. These may be used independently and may use 2 or more types.
- the curable resin composition of the present invention can be obtained by uniformly mixing the above components. Polymerization and curing of the curable resin composition of the present invention can be carried out by known methods. Curing can be performed in the presence or absence of a curing agent, and if necessary, for example, curing accelerators and inorganic fillers, compounding agents, various thermosetting resins/thermoplastic resins, reinforcing fibers, etc. If necessary, an extruder, a kneader, a blender, a roll, or the like is used to sufficiently mix until uniform to obtain the curable resin composition of the present invention. Then, the curable resin composition is molded by a melt casting method, a transfer molding method, an injection molding method, a compression molding method, or the like.
- the curing temperature cannot be categorically defined because it varies depending on whether or not a curing agent is used and the type of curing agent.
- the cured product of the present invention can be obtained by heating for a period of time. If the temperature is less than 20°C, sufficient curing cannot be obtained.
- a substrate obtained by impregnating a reinforcing fiber such as glass fiber, carbon fiber, aromatic polyamide fiber, silicon carbide fiber, or alumina fiber with the curable resin composition of the present invention is molded by filament winding and heated. It is also possible to obtain the cured product of the present invention.
- a solution obtained by dissolving the curable resin composition of the present invention in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, or methyl isobutyl ketone can also be used as a varnish, paint, or adhesive.
- the amount of the solvent used at this time is usually 5 to 90% by mass, preferably 10 to 80% by mass, based on the total amount of the curable resin composition of the present invention and the solvent.
- a varnish for circuit board materials can be produced by dissolving the curable resin composition of the present invention in a solvent such as toluene, xylene, tetrahydrofuran, or dioxolane.
- the circuit board material specifically includes a printed wiring board, a printed circuit board, a flexible printed wiring board, a build-up wiring board, and the like.
- the cured product obtained by curing the curable resin composition of the present invention can be used as moldings, laminates, castings, adhesives, coatings, and films.
- the cured product of the semiconductor encapsulant is a casting or molding.
- the compound is molded using a casting mold, a transfer molding machine, an injection molding machine, or the like, and further cured by heating at 80 to 230° C. for 0.5 to 10 hours. can get things.
- the cured product of the varnish for circuit boards is a laminate.
- a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper is impregnated with a varnish for a circuit board, dried by heating to obtain a prepreg, and then separated into individual pieces. or by laminating it with a metal foil such as a copper foil and subjecting it to heat press molding.
- the curable resin composition of the present invention can be used by being laminated with a metal foil (meaning including a metal plate; the same shall apply hereinafter).
- curable composite material of the curable resin composition of the present invention and its cured product (composite material cured product) will be described.
- a substrate is added to the curable composite material from the curable resin composition of the present invention to enhance mechanical strength and increase dimensional stability.
- Such substrates include, for example, various glass cloths such as roving cloth, cloth, chopped mat, surfacing mat, asbestos cloth, metal fiber cloth and other synthetic or natural inorganic fiber cloths, wholly aromatic polyamide fiber, wholly Woven or non-woven fabrics obtained from liquid crystal fibers such as aromatic polyester fibers and polybenzoxal fibers; woven or non-woven fabrics obtained from synthetic fibers such as polyvinyl alcohol fibers, polyester fibers and acrylic fibers; Cloth such as fiber cloth, carbon fiber cloth, kraft paper, cotton paper, paper-glass mixed fiber paper and other natural cellulose-based cloth, and paper. Each of these may be used alone, or two or more thereof may be used.
- the ratio of the base material to the curable composite material is 5 to 90% by mass, preferably 10 to 80% by mass, more preferably 20 to 70% by mass. If the base material is less than 5 mass %, the dimensional stability and strength of the curable composite material after curing tend to decrease. Moreover, when the base material is more than 90% by mass, the dielectric properties of the curable composite material tend to deteriorate.
- a coupling agent can be used in the curable composite material of the present invention, if necessary, for the purpose of improving the adhesion at the interface between the resin and the substrate. Common coupling agents such as silane coupling agents, titanate coupling agents, aluminum-based coupling agents, and zircoaluminate coupling agents can be used as the coupling agent.
- the curable resin composition of the present invention As a method for producing the curable composite material of the present invention, for example, the curable resin composition of the present invention and, if necessary, other components are mixed in a solvent such as the above-mentioned aromatic or ketone solvent or a mixed solvent thereof.
- a method of uniformly dissolving or dispersing the composition, impregnating it into the base material, and then drying the composition may be used. Impregnation is performed by immersion (dipping), coating, or the like. The impregnation can be repeated multiple times as necessary, and at this time, the impregnation can be repeated using a plurality of solutions with different compositions and concentrations to finally adjust the desired resin composition and resin amount. It is possible.
- a cured composite material can be obtained by curing the curable composite material of the present invention by a method such as heating.
- the production method is not particularly limited. For example, a plurality of curable composite materials are superimposed, each layer is adhered under heat and pressure, and heat curing is performed at the same time to obtain a composite material cured product having a desired thickness. be able to. It is also possible to combine a curable composite material that has once been adhesively cured with a curable composite material to obtain a cured composite material having a new layer structure. Lamination molding and curing are usually carried out simultaneously using a hot press or the like, but both may be carried out independently. That is, the uncured or semi-cured composite material obtained by laminating in advance can be cured by heat treatment or other treatment.
- Molding and curing are carried out at a temperature of 80 to 300° C., a pressure of 0.1 to 1000 kg/cm 2 and a time of 1 minute to 10 hours, more preferably a temperature of 150 to 250° C., a pressure of 1 to 500 kg/cm 2 and a time of 1. It can be done in the range of minutes to 5 hours.
- the laminate of the present invention is composed of a layer of the cured composite material of the present invention and a layer of metal foil.
- the metal foil used here include copper foil and aluminum foil.
- the thickness is not particularly limited, it is in the range of 3 to 200 ⁇ m, more preferably 3 to 105 ⁇ m.
- a curable composite material obtained from a curable resin composition and a substrate, and a metal foil are laminated in a layer configuration according to the purpose, and each interlayer is heated and pressurized.
- each interlayer is heated and pressurized.
- the laminate of the curable resin composition of the present invention the cured composite material and the metal foil are laminated in an arbitrary layer configuration.
- a metal foil can be used both as a surface layer and as an intermediate layer.
- lamination and curing can be repeated multiple times to form multiple layers.
- An adhesive can also be used to adhere to the metal foil.
- adhesives include, but are not limited to, epoxy, acrylic, phenol, cyanoacrylate, and the like. Laminate molding and curing can be performed under the same conditions as in the production of the cured composite material of the present invention.
- the curable resin composition of the present invention can also be molded into a film.
- the thickness is not particularly limited, it is in the range of 3 to 200 ⁇ m, more preferably 5 to 105 ⁇ m.
- the method for producing the film of the present invention is not particularly limited. a method of dissolving or dispersing the composition in the solvent, coating it on a resin film such as a PET film, and then drying it. The coating can be repeated multiple times as necessary, and it is also possible to repeat the coating using multiple solutions with different compositions and concentrations to finally adjust the desired resin composition and amount. is.
- the metal foil with resin of the present invention is composed of the curable resin composition of the present invention and a metal foil, and has a film formed from the curable resin composition on one side of the metal foil.
- the metal foil used here include copper foil and aluminum foil.
- the thickness is not particularly limited, it is in the range of 3 to 200 ⁇ m, more preferably 5 to 105 ⁇ m.
- the method for producing the resin-coated metal foil of the present invention is not particularly limited.
- a method of uniformly dissolving or dispersing the composition in the medium, applying the composition to a metal foil, and then drying the composition may be used.
- the application can be repeated multiple times as necessary, and at this time, the application can be repeated using a plurality of solutions with different compositions and concentrations, and finally the desired resin composition and amount can be adjusted. It is possible.
- Tg Glass transition temperature (Tg) According to IPC-TM-650 2.4.24.4, with a differential scanning calorimeter (manufactured by Hitachi High-Tech Science Co., Ltd., EXSTAR6000 DMS6100), when the measurement is performed under the temperature rising condition of 5 ° C./min. was expressed as the temperature of tan ⁇ .
- Thermal conductivity was measured by the unsteady hot wire method using a thermal conductivity meter (LFA447, manufactured by NETZSCH).
- A1 Poly(vinylbenzyl) ether compound (resin) obtained in Synthesis Example 1
- A2 Poly(vinylbenzyl) ether compound (resin) obtained in Synthesis Example 2
- B1 Alumina (manufactured by Denka Co., Ltd., DAM-05, average particle size 6.8 ⁇ m)
- B2 Boron nitride (manufactured by MARUKA Co., Ltd., AP-10S, average particle size 4.4 ⁇ m)
- C1 Styrene-modified polyphenylene ether resin (manufactured by Mitsubishi Gas Chemical Co., Ltd., OPE-2St 1200)
- C2 triallyl isocyanurate (manufactured by Mitsubishi Chemical Corporation, TAIC)
- D1 Styrene ethylene butylene styrene block copolymer (manufactured by Kraton, KRATON A1535, Mw 230,000)
- SN-495V naphthol aralkyl phenolic resin manufactured by Nippon Steel Chemical & Materials Co., Ltd.
- Ar 1 naphthalene ring in formula (2)
- Ar 2 benzene ring
- R 3 H
- the varnish was transferred to a dropping funnel and slowly added dropwise to a reaction vessel charged with a large amount of methanol. After dropping, solid-liquid separation was performed by decantation, and 1155 parts of methanol was added to the remaining solid. Solid-liquid separation was performed again by decantation, and this was repeated three times. 809 parts of toluene was added and dissolved again, and the mixture was washed with water twice. A portion of toluene was distilled to obtain a resin varnish of poly(vinylbenzyl) ether compound (A1). The non-volatile content of this resin varnish was measured and found to be 58.4%.
- the resulting poly(vinylbenzyl) ether compound (A1) had an n value (average) of 1.3, a number average molecular weight (Mn) of 831, and a weight average molecular weight (Mw) of 1,635.
- Mn number average molecular weight
- Mw weight average molecular weight
- the peak derived from the raw material disappeared, a new peak was formed on the high molecular weight side, the proton resonance line derived from vinylbenzyl chloride disappeared, and In addition, it was confirmed that the poly(vinyl It was confirmed that a benzyl) ether compound was obtained.
- the amount of residual hydroxyl groups was 14 ppm. Further, when the residual amount of vinylbenzyl chloride was measured by gas chromatography, it was 0.1% or less.
- the resulting poly(vinylbenzyl)ether compound (A2) had an n value (average) of 1.2, a number average molecular weight (Mn) of 702, and a weight average molecular weight (Mw) of 1,129.
- n value average
- Mn number average molecular weight
- Mw weight average molecular weight
- Example 1 Poly(vinylbenzyl) ether compound (A1) obtained in Synthesis Example 1 74.6 parts (solid content), 140 parts of B1, 0.5 parts of E1, 25.4 parts of F1, non-volatile matter is 50% was dissolved in toluene to obtain a curable resin composition varnish.
- the obtained curable resin composition varnish is applied to a PET film, dried in an oven at 130° C. for 5 minutes, pulverized into powder, filled in a mold, and vacuumed for 80 minutes at 210° C. and 2 MPa. Pressing was performed and thermal curing was performed to obtain a cured product having a thickness of 2 mm. The obtained cured product was measured for Tg, dielectric constant, dielectric loss tangent, thermal conductivity, coefficient of linear expansion, adhesive strength, and flame retardancy. Table 1 shows the measurement results.
- Example 2-8 Comparative Examples 1-5 According to the charged amount (part) of each raw material shown in Table 1, the same operation as in Example 1 was performed to obtain a curable resin composition varnish and a cured product. The same measurements as in Example 1 were performed, and the results are shown in Table 1.
- the curable resin composition of the present invention is extremely useful for applications such as electrical/electronic materials, lamination materials, molding materials, and casting materials.
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Abstract
La présente invention concerne : une composition de résine durcissable qui contient un éther poly(vinylbenzylique) et une charge inorganique, et qui fournit un produit durci qui présente une résistance à la chaleur, une faible tangente de perte diélectrique et une conductivité thermique élevée; et un produit durci de cette composition de résine durcissable. L'invention concerne une composition de résine durcissable qui est caractérisée en ce qu'elle contient : un éther poly(vinylbenzylique) qui est représenté par la formule (1), 90 % ou plus des positions de substitution des groupes vinyle dans les fractions vinylbenzyle étant des positions para; et une charge inorganique.
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PCT/JP2022/031080 WO2023026923A1 (fr) | 2021-08-26 | 2022-08-17 | Composition de résine durcissable, produit durci, matériau composite durcissable, matériau composite durci, vernis pour matériaux de carte de circuit imprimé, corps multicouche, feuille métallique avec résine, composant électrique/électronique, et matériau de carte de circuit imprimé |
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Citations (8)
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JP2002118031A (ja) * | 2000-10-10 | 2002-04-19 | Matsushita Electric Ind Co Ltd | 電子部品 |
JP2004042042A (ja) * | 2002-07-12 | 2004-02-12 | Ebara Corp | 固体反応剤 |
WO2014103926A1 (fr) * | 2012-12-27 | 2014-07-03 | 新日鉄住金化学株式会社 | Composé d'éther poly(vinylbenzylique), son procédé de production, composition durcissable le contenant, et article durci obtenu |
JP2015030776A (ja) * | 2013-08-01 | 2015-02-16 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、及び硬化物 |
JP2015067759A (ja) * | 2013-09-30 | 2015-04-13 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、硬化物、電気・電子部品及び回路基板材料 |
JP2015067797A (ja) * | 2013-09-30 | 2015-04-13 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、その硬化物、電気・電子部品及び回路基板 |
JP2015189926A (ja) * | 2014-03-28 | 2015-11-02 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、その硬化物、複合材料 |
WO2022107624A1 (fr) * | 2020-11-20 | 2022-05-27 | 日鉄ケミカル&マテリアル株式会社 | Composé d'éther poly(vinylbenzylique), composition de résine durcissable, produit durci, matériau composite durcissable, produit durci à base du matériau composite, stratifié, feuille métallique recouverte de résine, et procédé de production d'un composé d'éther poly(vinylbenzylique) |
-
2022
- 2022-08-16 TW TW111130794A patent/TW202323343A/zh unknown
- 2022-08-17 WO PCT/JP2022/031080 patent/WO2023026923A1/fr active Application Filing
- 2022-08-17 JP JP2023543845A patent/JPWO2023026923A1/ja active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002118031A (ja) * | 2000-10-10 | 2002-04-19 | Matsushita Electric Ind Co Ltd | 電子部品 |
JP2004042042A (ja) * | 2002-07-12 | 2004-02-12 | Ebara Corp | 固体反応剤 |
WO2014103926A1 (fr) * | 2012-12-27 | 2014-07-03 | 新日鉄住金化学株式会社 | Composé d'éther poly(vinylbenzylique), son procédé de production, composition durcissable le contenant, et article durci obtenu |
JP2015030776A (ja) * | 2013-08-01 | 2015-02-16 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、及び硬化物 |
JP2015067759A (ja) * | 2013-09-30 | 2015-04-13 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、硬化物、電気・電子部品及び回路基板材料 |
JP2015067797A (ja) * | 2013-09-30 | 2015-04-13 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、その硬化物、電気・電子部品及び回路基板 |
JP2015189926A (ja) * | 2014-03-28 | 2015-11-02 | 新日鉄住金化学株式会社 | 硬化性樹脂組成物、その硬化物、複合材料 |
WO2022107624A1 (fr) * | 2020-11-20 | 2022-05-27 | 日鉄ケミカル&マテリアル株式会社 | Composé d'éther poly(vinylbenzylique), composition de résine durcissable, produit durci, matériau composite durcissable, produit durci à base du matériau composite, stratifié, feuille métallique recouverte de résine, et procédé de production d'un composé d'éther poly(vinylbenzylique) |
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TW202323343A (zh) | 2023-06-16 |
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