WO2023286713A1 - 新規ポリマーおよびそれを含む樹脂組成物とその成形体 - Google Patents
新規ポリマーおよびそれを含む樹脂組成物とその成形体 Download PDFInfo
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- WO2023286713A1 WO2023286713A1 PCT/JP2022/027125 JP2022027125W WO2023286713A1 WO 2023286713 A1 WO2023286713 A1 WO 2023286713A1 JP 2022027125 W JP2022027125 W JP 2022027125W WO 2023286713 A1 WO2023286713 A1 WO 2023286713A1
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- 239000011342 resin composition Substances 0.000 title claims abstract description 82
- 229920000642 polymer Polymers 0.000 title claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000962 organic group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000000524 functional group Chemical group 0.000 claims abstract description 7
- -1 methacryloyl group Chemical group 0.000 claims description 154
- 229920005989 resin Polymers 0.000 claims description 91
- 239000011347 resin Substances 0.000 claims description 91
- 239000003822 epoxy resin Substances 0.000 claims description 75
- 229920000647 polyepoxide Polymers 0.000 claims description 75
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 26
- 239000002184 metal Substances 0.000 claims description 26
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- 239000005062 Polybutadiene Substances 0.000 claims description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 229920001955 polyphenylene ether Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 239000002966 varnish Substances 0.000 claims description 17
- 239000012212 insulator Substances 0.000 claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 claims description 16
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 14
- 239000002313 adhesive film Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 113
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- 238000001723 curing Methods 0.000 description 45
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- 239000000047 product Substances 0.000 description 29
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- 239000010410 layer Substances 0.000 description 26
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 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 18
- 229920001577 copolymer Polymers 0.000 description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
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- 230000009477 glass transition Effects 0.000 description 13
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
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- 239000003505 polymerization initiator Substances 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003431 cross linking reagent Substances 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 9
- 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 8
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 239000007822 coupling agent Substances 0.000 description 8
- 239000004643 cyanate ester Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000011572 manganese Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 125000004437 phosphorous atom Chemical group 0.000 description 7
- 229920002401 polyacrylamide Polymers 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
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- 239000002585 base Substances 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 238000000113 differential scanning calorimetry Methods 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
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- 239000011256 inorganic filler Substances 0.000 description 6
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- 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 description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
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- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
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- 238000000465 moulding Methods 0.000 description 5
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 5
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 5
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- 150000002978 peroxides Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 4
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 4
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
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- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
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- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 4
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- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
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- 239000002518 antifoaming agent Substances 0.000 description 3
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- 238000000518 rheometry Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000012899 standard injection Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer 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
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 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
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- 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
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
- C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/126—Polyphenylene oxides modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09D171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09D171/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C09J171/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C09J171/12—Polyphenylene oxides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes epoxy resins
-
- 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
- H05K1/0313—Organic insulating material
-
- 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
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0346—Organic insulating material consisting of one material containing N
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/08—Homopolymers or copolymers of acrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2433/24—Homopolymers or copolymers of amides or imides
- C08J2433/26—Homopolymers or copolymers of acrylamide or methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2433/00—Presence of (meth)acrylic polymer
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2463/00—Presence of epoxy resin
-
- 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
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
Definitions
- the present invention relates to a polymer that has excellent heat resistance and dielectric properties and is soluble in an organic solvent at a high concentration, a resin composition containing the same, and a molded article thereof.
- the resin used in the manufacture of printed wiring boards has high heat resistance (high glass transition point) and dissolves at high concentrations in common varnish organic solvents such as methyl ethyl ketone (MEK), toluene, and cyclohexanone. are required to do so.
- MEK methyl ethyl ketone
- Patent Document 1 discloses a polyarylate resin.
- the present invention provides a polymer having a low dielectric constant and a low dielectric loss tangent, a high glass transition point, high solubility in organic solvents, and high compatibility with thermosetting resins, a resin composition containing the polymer, and a molded article thereof. intended to provide
- X 1 and X 2 each independently represent a C3-C6 branched alkyl group, a C3-C6 cyclic alkyl group, a C3-C6 branched alkoxy group or a C3-C6 cyclic alkoxy group; n is 0 or 1;
- Z 1 and Z 2 each independently represent a single bond or a C1-C3 alkylene group, each R independently represents an organic group or a halogeno group, m1 and m2 each independently represents an integer from 0 to 4, and Y represents a polymerizable functional group.
- a resin composition containing the polymer described in (1) A resin composition containing the polymer described in (1).
- the resin composition according to (3) which further contains a resin other than the polymer according to (1).
- the resin composition according to (4), wherein the resin other than the polymer according to (1) is a thermosetting resin.
- the resin composition according to (5), wherein the thermosetting resin is an epoxy resin.
- thermosetting resin is a maleimide compound having one or more maleimide groups; polyphenylene ether compounds, Polybutadiene having a molar ratio of 1,2 bond structure and 1,4 bond structure of 80:20 to 100:0; A styrene-butadiene-styrene block copolymer (SBS) having a molar ratio of 1,2-linked structure and 1,4-linked structure in the butadiene block of 80:20 to 100:0, and formula (V) in the molecule (In formula (V), Z 3 represents a C6-C12 arylene group, and R 2 -R 7 each independently represent a hydrogen atom or a C1-C6 alkyl group.)
- SBS styrene-butadiene-styrene block copolymer
- Z 3 represents a C6-C12 arylene group
- R 2 -R 7 each independently represent a hydrogen atom or a C1-C6 alkyl group.
- An adhesive film comprising a resin composition layer containing the resin composition according to any one of (3) to (9) on a support film.
- An insulator for printed wiring boards comprising a cured product of the prepreg described in (13).
- An insulator for printed wiring boards comprising a cured product of the adhesive film described in (14).
- a laminate with a metal foil comprising a layer made of the printed wiring board insulator according to (15) and a layer made of a metal foil.
- a laminate with a metal foil comprising a layer comprising the printed wiring board insulator according to (16) and a layer comprising a metal foil.
- a compound represented by formula (III). (wherein X 1 and X 2 each independently represent a C3-C6 branched alkyl group, a C3-C6 cyclic alkyl group, a C3-C6 branched alkoxy group or a C3-C6 cyclic alkoxy group; n is 0 or 1; , Z 1 and Z 2 each independently represent a single bond or a C1-C3 alkylene group, each R independently represents an organic group or a halogeno group, m1 and m2 each independently represents an integer from 0 to 4, and Y represents a polymerizable functional group.) (20) The compound according to (19), wherein the compound represented by formula (III) is a compound represented by formula (IV). (Wherein, R 1 represents a hydrogen atom or a methyl group)
- the novel polymer of the present invention has a low dielectric constant and low dielectric loss tangent, has a high glass transition point, and exhibits high solubility in organic solvents.
- polymer of the present invention has a repeating unit derived from the polymerizable compound represented by Formula (I).
- X 1 and X 2 each independently represent a C3-C6 branched alkyl group, a C3-C6 cyclic alkyl group, a C3-C6 branched alkoxy group or a C3-C6 cyclic alkoxy group.
- the "C3-C6 branched alkyl group" for X 1 and X 2 includes isopropyl group, sec-butyl group, isobutyl group, tert-butyl group, neopentyl group, isopentyl group, sec-pentyl group, and 1-ethylpropyl group. , tert-pentyl group, isohexyl group, 3-methylpentyl group, 2,2-dimethylbutyl group, 2,3-dimethylbutyl group and the like.
- the “C3-C6 cyclic alkyl group” for X 1 and X 2 includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
- the "C3-C6 branched alkoxy group” for X 1 and X 2 includes an isopropyloxy group, a sec-butyloxy group, an isobutyloxy group, a tert-butyloxy group, a neopentyloxy group, an isopentyloxy group and a sec-pentyloxy group.
- C3-C6 cyclic alkoxy group examples include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like.
- X 1 and X 2 are preferably C3-C6 branched alkyl groups, more preferably tert-butyl groups.
- n 0 or 1. n is preferably one.
- Z 1 and Z 2 each independently represent a single bond or a C1-C3 alkylene group.
- the C1-C3 alkylene group for Z 1 and Z 2 includes methylene, ethylene, propane-1,3-diyl and the like.
- Z 1 and Z 2 are preferably single bonds.
- each R independently represents an organic group or a halogeno group.
- the "organic group” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
- Examples of organic groups include methyl group, ethyl group, n-propyl group, I-propyl group, n-butyl group, s-butyl group, I-butyl group, t-butyl group, n-pentyl group and n-hexyl group.
- C1-6 alkyl groups such as phenyl group, C6-10 aryl groups such as naphthyl group, methoxy group, ethoxy group, n-propoxy group, I-propoxy group, n-butoxy group, s-butoxy group, I -Butoxy group, C1-6 alkoxy groups such as t-butoxy group, chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, per Examples thereof include C1-6 haloalkyl groups such as fluoro-n-pentyl group.
- a "halogeno group” includes a fluoro group, a chloro group, a bromo group, and an iodo group.
- n1 and m2 each independently represent an integer of 0 to 4. m1 and m2 are preferably zero.
- Y represents a polymerizable functional group.
- polymerizable functional groups include polymerizable carbon-carbon groups such as vinyl group, allyl group, acryloyl group, methacryloyl group, vinyloxycarbonyl group, prop-1-en-2-yloxycarbonyl group and allyloxycarbonyl group. A group having a double bond and the like can be mentioned.
- Y is preferably an acryloyl group or a methacryloyl group, more preferably an acryloyl group.
- the above formula (I) includes compounds represented by the following formula (II).
- Y, Z 1 , Z 2 , X 1 , R, m1 and m2 are the same as described in formula (I).
- X 3 represents a C3-C6 branched alkyl group, a C3-C6 cyclic alkyl group, a C3-C6 branched alkoxy group, a C3-C6 cyclic alkoxy group, a hydrogen atom, an organic group or a halogeno group, Among them, a C3-C6 branched alkyl group, a C3-C6 cyclic alkyl group or a C3-C6 branched alkoxy group is preferable, a C3-C6 branched alkyl group is more preferable, and a tert-butyl group is particularly preferable.
- the C3-C6 branched alkyl group, C3-C6 cyclic alkyl group, C3-C6 branched alkoxy group, and C3-C6 cyclic alkoxy group for X 3 are the C3-C6 branched alkyl group, C3-C6 branched alkyl group for X1 and X2 in formula (I).
- the same groups as ⁇ C6 cyclic alkyl group, C3-C6 branched alkoxy group and C3-C6 cyclic alkoxy group can be mentioned.
- R 1 represents a hydrogen atom or a methyl group
- R 1 is preferably a hydrogen atom.
- the polymer having a repeating unit derived from a polymerizable compound represented by formula (I) used in the present invention is a polymer comprising at least one repeating unit derived from a polymerizable compound represented by the following formula (I), or , a polymer comprising at least one repeating unit and at least one repeating unit derived from another radically polymerizable compound.
- formula (I) each symbol is as described above. That is, the polymer used in the present invention specifically includes the following polymers.
- the polymer having a repeating unit derived from the polymerizable compound represented by formula (I) is I) a homopolymer consisting of one type of repeating unit derived from the polymerizable compound represented by formula (I), or III) Formula ( It is preferably a copolymer comprising at least one repeating unit derived from the polymerizable compound represented by I) and at least one repeating unit derived from another radically polymerizable compound, and I) represented by formula (I) More preferably, it is a homopolymer composed of one of the repeating units derived from the polymerizable compound represented.
- each repeating unit may be randomly arranged, alternately arranged, or block arranged.
- the molecular chain may be linear or branched.
- the branched chain include a branched chain formed by branching at one point (star type), a branched chain formed by branching at a plurality of points (graft type), and the like.
- the weight average molecular weight of the polymer of the present invention is not limited, and is 000, 20,000 to 100,000 and the like. Further, the molecular weight distribution (PDI) of the polymer according to the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 4.0, as a ratio of weight average molecular weight/number average molecular weight (Mw/Mn). 0, most preferably 1.0 to 3.0.
- the weight average molecular weight and number average molecular weight are values obtained by converting data measured by gel permeation chromatography (GPC) using THF as a solvent based on the molecular weight of polymethyl methacrylate used as a standard.
- the "other radically polymerizable compound” is a radically polymerizable compound other than the compound represented by formula (I), and may be appropriately selected according to the desired physical properties such as melting point, viscosity or refractive index.
- (meth) acrylic acids, (meth) acrylonitrile, styrenes, vinyl compounds, olefin compounds, unsaturated carboxylic acid anhydrides, etc. and one or more of these can be used.
- compounds similar to those exemplified for the component (1) radically polymerizable compound can be mentioned.
- "(meth)acryl” means "acryl” and/or "methacryl”.
- (meth)acrylic acids such as (meth)acrylates and (meth)acrylamides, unsaturated dicarboxylic acid anhydrides, and styrenes are preferable as the “other radically polymerizable compound”.
- (Meth)acrylates include alkyl (meth)acrylates, acrylates having an alicyclic hydrocarbon group, (meth)acrylates having an ether skeleton, (meth)acrylates having a cyclic ether skeleton, and (meth)acrylates having an aromatic group. acrylates, etc.
- Alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, and t-butyl (meth)acrylate.
- (Meth)acrylates having an alicyclic hydrocarbon group include cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, isobornyl (Meth)acrylates and methoxylated cyclodecatriene (meth)acrylates.
- (Meth)acrylates having an ether skeleton include 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, and diethylene glycol monomethyl ether (meth)acrylate.
- Examples of (meth)acrylates having a cyclic ether skeleton include glycidyl (meth)acrylate, furfuryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 3-ethyl-3-oxetanylmethyl (meth)acrylate, (2-methyl- Ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate, ⁇ -butyrolactone (meth)acrylate, dioxolane (meth)acrylate, oxetane (meth)acrylate, (meth) ) acryloylmorpholine and the like.
- (Meth)acrylates having an aromatic group include phenyl (meth)acrylate, benzyl (meth)acrylate, methylbenzyl (meth)acrylate, ethylbenzyl (meth)acrylate, propylbenzyl (meth)acrylate, methoxybenzyl (meth)acrylate, Acrylate, phenoxyethyl (meth)acrylate, chlorobenzyl (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate and the like.
- (Meth)acrylamides include methyl (meth)acrylamide, dimethyl (meth)acrylamide, ethyl (meth)acrylamide, hydroxyethyl (meth)acrylamide, diethyl (meth)acrylamide, n-propyl (meth)acrylamide, and dipropyl (meth)acrylamide.
- unsaturated dicarboxylic anhydrides include maleic anhydride, citraconic anhydride, and itaconic anhydride.
- Styrenes include styrene, p-hydroxystyrene, p-chlorostyrene, p-bromostyrene, p-methylstyrene, p-methoxystyrene, pt-butoxystyrene, pt-butoxycarbonylstyrene and the like.
- Other examples include vinyl compounds such as vinyl acetate, vinyl chloride, vinylidene chloride, (meth)acrylonitrile, vinyl ether, acrolein and divinylbenzene; and olefin compounds such as ethylene, propylene and butadiene.
- composition ratio of repeating unit In the polymer used in the present invention, the content of the repeating unit derived from the polymerizable compound represented by formula (I) and the repeating unit derived from other radically polymerizable isomer compound is not particularly limited as long as the effect of the present invention is exhibited. .
- the weight ratio of the repeating unit derived from the polymerizable compound represented by formula (I) and the repeating unit derived from the other radically polymerizable isomer compound is 99.5:0.5 to 0.5:99.5,99 A range such as 5:0.5 to 30:70, 99:1 to 30:70, 90:10 to 30:70, 60:40 to 30:70 can be selected.
- the compound represented by the formula (I), which is the polymerizable compound used in the present invention can be synthesized by the methods of Examples and other known methods.
- Y in formula (I) is an acryl group or a methacryl group
- it can be produced by the following method.
- a secondary amine represented by the formula (I′) and a (meth)acrylic acid halide such as (meth)acrylic acid chloride are reacted in a solvent in the presence of a base.
- the solvent examples include amide solvents such as N,N-dimethylformamide (DMF) and N,N-dimethylacetamide, ether solvents such as tetrahydrofuran (THF), 1,2-dimethoxyethane, diethyl ether and methyl cellosolve, Aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene, dichlorobenzene and benzonitrile; saturated hydrocarbons such as pentane, hexane, octane and cyclohexane; halogens such as dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane ketone solvents such as hydrocarbons, acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; and ester solvents such as ethyl acetate, butyl acetate and 2-
- the base examples include aliphatic amines such as triethylamine and tributylamine; aromatic amines such as pyridine, N-ethylpyridine, N,N-dimethylaniline and N,N-dimethylaminopyridine; Organic bases such as metal alkoxides, alkali metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, calcium hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, sodium hydrogen carbonate Alternatively, inorganic bases such as alkaline earth metal hydroxides, alkali metal or alkaline earth metal carbonates can be used.
- the reaction temperature is -50°C to 200°C.
- the polymer used in the present invention may be used without particular limitation as long as it is obtained by polymerizing at least one polymerizable compound represented by formula (I), or by polymerizing the compound and another polymerizable compound.
- the polymerization reaction is not particularly limited, and may be a known method for synthesizing polyacrylate or the like, such as radical polymerization, anionic polymerization, cationic polymerization, ring-opening polymerization, coordination polymerization, and the like. An example is shown in the example.
- Y in formula (I) is an acrylic group or a methacrylic group and (meth)acrylate
- the polymerizable compound represented by formula (I) and (meth)acrylate are mixed in a solvent
- a polymerization reaction is carried out by heating or light irradiation in the presence of a radical polymerization initiator.
- the polymerization solvent is not particularly limited as long as it does not participate in the polymerization reaction and is compatible with the polymer.
- Ester-based compounds such as ethyl acetate, ketone-based compounds such as methyl ethyl ketone and cyclohexanone, and aliphatic, aromatic or alicyclic hydrocarbon compounds such as hexane and toluene. can be done. These solvents can be used singly or as a mixed solvent of two or more.
- radical polymerization initiators include azobisisobutyronitrile, azobis-2,4-dimethylvaleronitrile, azobiscyclohexanecarbonitrile, azobis-2-amidinopropane hydrochloride, potassium peroxodisulfate, and ammonium peroxodisulfate. , t-butyl hydroperoxide, di-t-butyl cumene hydroperoxide, acetyl peroxide, benzoyl peroxide, lauroyl peroxide and the like.
- the resin composition of the present invention contains a polymer (hereinafter also referred to as "(A) component”) composed of at least one repeating unit derived from the polymerizable compound represented by the above formula (I). .
- the resin composition of the present invention further includes, as components other than component (A), curable resins such as ionizing radiation curable resins and thermosetting resins (hereinafter also referred to as “component (B)”) and other components.
- curable resins include (meth)acrylic resins, vinyl resins, allyl resins, melamine resins, urethane resins, epoxy resins, silicone resins, polyester resins, and polyamic acid resins.
- Resins polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, maleimide resins, cyanate resins, and the like can be used.
- ionizing radiation-curable resin refers to a resin that is cured by irradiation with ionizing radiation including all electromagnetic waves such as infrared rays, visible rays, ultraviolet rays, X-rays, and electron beams.
- the ionizing radiation-curable resin and thermosetting resin are not particularly limited, but monomers, prepolymers, oligomers, polymers, etc. having vinyl groups, (meth)acryloyl groups, epoxy groups, oxetanyl groups, and maleimide groups are used. be able to. Among them, it is preferable to use a polyfunctional resin.
- a "(meth)acryloyl group” means an "acryloyl group” and/or a "methacryloyl group.” Examples of the thermosetting resin used as the resin composition of the present invention are specifically described below.
- Epoxy resin (hereinafter also referred to as "(B-1) component")
- epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol novolac type epoxy resin, Phenol novolak type epoxy resin, alicyclic epoxy resin having an ester skeleton, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy Resins, cresol novolak type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexanedimethanol type epoxy resin
- the epoxy resin preferably contains an epoxy resin having two or more epoxy groups in one molecule.
- the non-volatile component of the epoxy resin is 100 mass %
- at least 50 mass % or more of the epoxy resin preferably has two or more epoxy groups in one molecule.
- an epoxy resin that has two or more epoxy groups in one molecule and is liquid at a temperature of 20 ° C. (hereinafter referred to as "liquid epoxy resin"), and three or more epoxy groups in one molecule, It preferably contains an epoxy resin that is solid at a temperature of 20° C. (hereinafter referred to as “solid epoxy resin”).
- solid epoxy resin By using both a liquid epoxy resin and a solid epoxy resin as epoxy resins, a resin composition having excellent flexibility can be obtained. Moreover, the breaking strength of the cured product of the resin composition is also improved.
- Liquid epoxy resins include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, phenol novolak type epoxy resin, and alicyclic epoxy resin having an ester skeleton.
- epoxy resins having a butadiene structure are preferred, and bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, alicyclic epoxy resins having an ester skeleton, and naphthalene type epoxy resins are more preferred, and bisphenol A type epoxy resins and bisphenol AF type epoxy resins are more preferable, and bisphenol AF type epoxy resins are particularly preferable from the viewpoint of excellent physical property balance of cured products.
- Solid epoxy resins include naphthalene type tetrafunctional epoxy resin, cresol novolak type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol type epoxy resin, biphenyl type epoxy resin, naphthylene ether type epoxy resin, Anthracene-type epoxy resin, bisphenol A-type epoxy resin, and tetraphenylethane-type epoxy resin are preferable, naphthalene-type tetrafunctional epoxy resin, naphthol-type epoxy resin, and biphenyl-type epoxy resin are more preferable, and biphenyl-type epoxy resin is particularly preferable.
- a curing agent may be included.
- Curing agents for epoxy resins are not particularly limited, but include phenol-based curing agents, naphthol-based curing agents, active ester-based curing agents, benzoxazine-based curing agents, cyanate ester-based curing agents, acid anhydride-based curing agents, and the like.
- a cyanate ester-based curing agent and an active ester-based curing agent are preferred from the viewpoint of lowering the dielectric loss tangent. These may be used singly or in combination of two or more.
- phenol-based curing agent and naphthol-based curing agent examples include, but are not particularly limited to, a phenol-based curing agent having a novolak structure and a naphthol-based curing agent having a novolak structure, and include phenol novolak resins, triazine skeleton-containing phenol novolak resins, and naphthol novolacs. Resins, naphthol aralkyl type resins, triazine skeleton-containing naphthol resins, and biphenyl aralkyl type phenol resins are preferred.
- active ester-based curing agent compounds having two or more active ester groups in one molecule are preferred, such as phenol esters, thiophenol esters, N-hydroxyamine esters, esters of heterocyclic hydroxy compounds, and the like.
- a compound having two or more highly reactive ester groups in one molecule is preferably used.
- An active ester compound may be used individually by 1 type, and may be used in combination of 2 or more type.
- an active ester compound obtained by a condensation reaction between a carboxylic acid compound and/or a thiocarboxylic acid compound and a hydroxy compound and/or a thiol compound is preferred.
- an active ester compound obtained by reacting a carboxylic acid compound with one or more selected from a phenol compound, a naphthol compound and a thiol compound is more preferable, and a carboxylic acid compound and an aromatic compound having a phenolic hydroxyl group.
- an aromatic compound having two or more active ester groups in one molecule Obtained by reacting, more preferably an aromatic compound having two or more active ester groups in one molecule, a carboxylic acid compound having at least two or more carboxy groups in one molecule, and a phenolic hydroxyl group
- An aromatic compound obtained by reacting with an aromatic compound and having two or more active ester groups in one molecule is even more preferable.
- the active ester compound may be linear or branched.
- carboxylic acid compounds include aliphatic carboxylic acids having 1 to 20 carbon atoms (preferably 2 to 10, more preferably 2 to 8) and aromatic compounds having 7 to 20 carbon atoms (preferably 7 to 10). Carboxylic acids are mentioned. Examples of aliphatic carboxylic acids include acetic acid, malonic acid, succinic acid, maleic acid and itaconic acid. Examples of aromatic carboxylic acids include benzoic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.
- succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, and isophthalic acid and terephthalic acid are more preferred, from the viewpoint of heat resistance.
- the thiocarboxylic acid compound is not particularly limited, but includes, for example, thioacetic acid, thiobenzoic acid and the like.
- phenolic compound examples include phenolic compounds having 6 to 40 carbon atoms (preferably 6 to 30, more preferably 6 to 23, and still more preferably 6 to 22).
- Preferred specific examples include hydroquinone, Resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalin, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, dihydroxybenzophenone, tri Hydroxybenzophenone, tetrahydroxybenzophenone, phloroglucine, benzenetriol, dicyclopentadiene type diphenol and the like.
- a phenol novolak and a phosphorus atom-containing oligomer having a phenolic hydroxyl group described in JP-A-2013-40270 may also be used.
- naphthol compounds include naphthol compounds having 10 to 40 carbon atoms (preferably 10 to 30, more preferably 10 to 20 carbon atoms). ,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene and the like. Naphthol novolacs may also be used as naphthol compounds.
- the thiol compound is not particularly limited, but includes, for example, benzenedithiol, triazinedithiol, and the like.
- the active ester compound examples include an active ester compound containing a dicyclopentadiene type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetylated phenol novolac, and a benzoylated phenol novolak.
- Examples include active ester compounds and active ester compounds obtained by reacting an aromatic carboxylic acid with a phosphorus atom-containing oligomer having a phenolic hydroxyl group. Active ester compounds and active ester compounds obtained by reacting an aromatic carboxylic acid with a phosphorus atom-containing oligomer having a phenolic hydroxyl group are more preferable.
- the "dicyclopentadiene-type diphenol structure" represents a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.
- the active ester compound As the active ester compound, the active ester compounds disclosed in JP-A-2004-277460 and JP-A-2013-40270 may be used, and commercially available active ester compounds may also be used.
- commercially available active ester compounds include, for example, active ester compounds containing a dicyclopentadiene type diphenol structure such as EXB9451, EXB9460, EXB9460S, HPC-8000-65T (manufactured by DIC Corporation), active esters containing a naphthalene structure, EXB9416-70BK (manufactured by DIC Corporation) as an ester compound, DC808 (manufactured by Mitsubishi Chemical Corporation) as an active ester compound containing an acetylated product of phenol novolac, and YLH1026 (manufactured by Mitsubishi Chemical Corporation) as an active ester compound containing a benzoylated product of phenol novolac (manufactured by DIC Corporation
- cyanate ester curing agent examples include, but are not limited to, novolac type (phenol novolak type, alkylphenol novolak type, etc.) cyanate ester type curing agent, dicyclopentadiene type cyanate ester type curing agent, bisphenol type (bisphenol A type, bisphenol F type, bisphenol S type, etc.), cyanate ester-based curing agents, and prepolymers obtained by partially triazinizing these.
- the weight average molecular weight of the cyanate ester curing agent is not particularly limited, but is preferably 500-4500, more preferably 600-3000.
- cyanate ester curing agents include bisphenol A dicyanate, polyphenolcyanate (oligo(3-methylene-1,5-phenylenecyanate), 4,4′-methylenebis(2,6-dimethylphenylcyanate), 4,4′-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatophenylmethane), bis(4-cyanate-3, Bifunctional cyanate resins such as 5-dimethylphenyl)methane, 1,3-bis(4-cyanatophenyl-1-(methylethylidene))benzene, bis(4-cyanatophenyl)thioether, and bis(4-cyanatophenyl)ether , polyfunctional cyanate resins derived from phenol novolak, cresol novolac, dicyclopentadiene structure-containing phenol resins, etc., and
- the acid anhydride-based curing agent is not particularly limited, but includes phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, and methyl hydride.
- the curing accelerator is not particularly limited, but includes amine-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, phosphonium-based curing accelerators, and the like. These may be used singly or in combination of two or more.
- the amine curing accelerator is not particularly limited, but trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1, Amine compounds such as 8-diazabicyclo(5,4,0)-undecene (hereinafter abbreviated as DBU) are included. These may be used singly or in combination of two or more.
- trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1, Amine compounds such as 8-diazabicyclo(5,4,0)-undecene (hereinafter abbreviated as DBU) are included. These may be used singly or in combination of two or more.
- the guanidine curing accelerator is not particularly limited, but dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4 .0] Dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexyl biguanide, 1-allylbiguanide, 1-phenylbiguanide, 1-(o-tolyl)big
- the imidazole curing accelerator is not particularly limited, but 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2- Dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2- methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1 -cyanoethyl-2-phenylimidazolium trimell
- the metal-based curing accelerator is not particularly limited, but examples include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin.
- organometallic complexes include organocobalt complexes such as cobalt (II) acetylacetonate and cobalt (III) acetylacetonate, organocopper complexes such as copper (II) acetylacetonate, and zinc (II) acetylacetonate.
- organic zinc complexes such as iron (III) acetylacetonate; organic nickel complexes such as nickel (II) acetylacetonate; and organic manganese complexes such as manganese (II) acetylacetonate.
- Organic metal salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate and the like. These may be used singly or in combination of two or more.
- Phosphonium-based curing accelerators are not particularly limited. Alkoxyphenyl)phosphine, Tris(dialkylphenyl)phosphine, Tris(trialkylphenyl)phosphine, Tris(tetraalkylphenyl)phosphine, Tris(dialkoxyphenyl)phosphine, Tris(trialkoxyphenyl)phosphine, Tris(tetraalkoxyphenyl) organic phosphines such as phosphine, trialkylphosphine, dialkylarylphosphine and alkyldiarylphosphine; Phosphonium borate compounds, complexes of organic phosphines and organic borons such as tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate; (4-methylphenyl)triphenylphosphonium thio
- the tertiary phosphine is not particularly limited. methoxyphenyl)phosphine and the like.
- examples of quinones include o-benzoquinone, p-benzoquinone, diphenoquinone, 1,4-naphthoquinone and anthraquinone. These may be used singly or in combination of two or more.
- the curing accelerator used in the resin composition of the present invention is preferably an amine-based curing accelerator.
- a maleimide compound having one or more maleimide groups (hereinafter also referred to as "(B-2) component")
- the maleimide compound used in the present invention is not particularly limited as long as it is a compound having one or more maleimide groups in the molecule.
- N-phenylmaleimide N-hydroxyphenylmaleimide, bis(4-maleimidophenyl)methane, 2,2-bis ⁇ 4-(4-maleimidophenoxy)-phenyl ⁇ propane, bis(3 ,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(3,5-diethyl-4-maleimidophenyl)methane, polytetramethylene oxide-bis (4-maleimidobenzoate), 2,2-bis[4-(4-maleimidophenoxy)phenyl]propane, a maleimide compound represented by the following formula (VII), a maleimide compound represented by the following formula (IX), these Examples include prepolymers of maleimide compounds and prepolymers of maleimide compounds and amine compounds. These may be used singly or in admixture of two or more.
- R 11 and R 12 are each independently a halogeno group, a C1-C6 alkyl group, a hydroxyl group, a C1-C6 alkoxy group, a formyl group, a carboxyl group, a C1-C6 alkoxycarbonyl group, a C6-C10 aryl group, an amino group , a C1-C6 alkyl group-substituted amino group, a cyano group, or a nitro group, a1 and a2 each independently represent an integer of 0 to 4; when a1 is 2 or more, R 11 may be the same or different; when a2 is 2 or more, R 12 may be the same or different; Often, m3 and m4 each independently represent an integer of 1 to 10, R 13 and R 14 are each independently a C1-C6 alkyl group or a C6-C10 aryl group; a3 represents an integer of 0 to 3, and when a3 is
- halogeno group examples include a fluoro group, a chloro group, a bromo group, an iodo group and the like.
- C1-C6 alkyl group examples include linear or branched.
- C1-C6 alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, I-propyl group, I-butyl group, s-butyl group, t -butyl group, I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, I-hexyl group and the like.
- the "C1-C6 alkoxy group” for R 11 and R 12 includes methoxy, ethoxy, n-propoxy, I-propoxy, n-butoxy, s-butoxy, I-butoxy and t-butoxy. and the like.
- the "C1-C6 alkoxycarbonyl group” for R 11 and R 12 includes a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, I-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like. can be mentioned.
- Examples of the “C6-C10 aryl group” for R 11 and R 12 include a phenyl group and a naphthyl group.
- the “C1-C6 alkyl group-substituted amino group” for R 11 and R 12 may be either mono-substituted or di-substituted.
- Examples of the "C1-C6 alkyl group-substituted amino group” include methylamino group, dimethylamino group, ethylamino group, diethylamino group, methylethylamino group and the like.
- a1 and a2 are 0.
- n3 and m4 are preferably 1 to 6, more preferably 1 to 3, even more preferably 1 to 2, and particularly preferably 1.
- Examples of the C1-C6 alkyl group and C6-C10 aryl group for R 13 and R 14 are the same as those exemplified for R 11 and R 12 .
- a3 and a4 are preferably 0.
- n1 is preferably 1-50, more preferably 1-20, even more preferably 1-5.
- n2 represents an integer of 1-100. n2 is preferably 1-50, more preferably 1-20, even more preferably 1-5.
- R 15 and R 16 each independently represent a hydrogen atom or a C1-C6 alkyl group
- n3 represents an integer of 1-10
- X 4 and X 5 each independently represents a C1 to C6 alkyl group
- S1 and S2 each independently represents an integer of 0 to 2
- S2 is When 2, X 5 may be the same or different.
- Examples of the “C1-C6 alkyl group” for R 15 and R 16 include those exemplified for R 11 and R 12 .
- R 15 and R 16 are preferably hydrogen atoms or methyl groups, more preferably hydrogen atoms.
- n3 is preferably an integer of 1-7.
- X 4 and X 5 examples include those exemplified for R 11 and R 12 .
- X 4 and X 5 are preferably methyl or ethyl groups.
- the compound represented by formula (IX) is preferably 4,4'-diphenylmethanebismaleimide or bis(3-ethyl-5-methyl-4-maleimidophenyl)methane.
- the maleimide compound used in the present invention is preferably a maleimide compound represented by formula (VII) or a maleimide compound represented by formula (IX), a compound represented by formula (VIII), or a compound represented by formula ( More preferably, it is a maleimide compound represented by IX).
- a commercially available product can be used as the maleimide compound.
- Commercially available products include, for example, MIR-3000 (manufactured by Nippon Kayaku Co., Ltd.), MIR-3000-70MT (manufactured by Nippon Kayaku Co., Ltd.), BMI (manufactured by K.I. Kasei Co., Ltd.), BMI-70 (K.I. Kasei Co., Ltd.) ), BMI-80 (manufactured by K-I Kasei Co., Ltd.), and the like.
- the polyphenylene ether compound used in the present invention is not particularly limited as long as it is a polymer having repeating units represented by the following formula (X).
- R 17 to R 20 are each independently a hydrogen atom, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C2 to C6 alkynyl group, a C1 to C6 alkylcarbonyl group, or a C2 to C6 alkenyl indicates a carbonyl group.
- Examples of the “C1-C6 alkyl group” for R 17 to R 20 include the same groups as exemplified for R 11 and R 12 .
- Examples of the “C2-C6 alkenyl group” for R 17 to R 20 include a vinyl group and an allyl group.
- Examples of the “C2-C6 alkynyl group” for R 17 to R 20 include ethynyl, 2-propynyl and the like.
- Examples of the “C1-C6 alkylcarbonyl group” for R 17 to R 20 include an acetyl group.
- Examples of the “C2-C6 alkenylcarbonyl group” for R 17 to R 20 include an acryloyl group and a methacryloyl group.
- R 17 to R 20 are preferably a hydrogen atom, a C1-C6 alkyl group or a C2-C6 alkenyl group, more preferably a hydrogen atom, a methyl group or an allyl group, and a hydrogen atom or a methyl group is more preferable.
- terminal-modified polyphenylene ether compounds include terminal-modified polyphenylene ether compounds with hydroxyl groups and carbon-carbon polyphenylene ether compounds modified with substituents having unsaturated double bonds.
- Examples of the substituent having a carbon-carbon unsaturated double bond include a group represented by formula (VI), an acryloyl group, or a methacryloyl group.
- * represents a bonding position
- p represents an integer of 0 to 10
- Z 4 represents an arylene group
- R 8 to R 10 each independently represent a hydrogen atom, or C1 A ⁇ C6 alkyl group is shown.
- a phenylene group can be mentioned as the C6-C12 arylene group for Z 4 .
- Examples of the C1-C6 alkyl group for R 8 to R 10 include those exemplified for R 11 and R 12 .
- formula (VI) Specific examples of the group represented by formula (VI) include groups represented by formula (VI-1) and formula (VI-2). In formulas (VI-1) and (VI-2), * indicates a binding position.
- polyphenylene ether compounds modified with substituents having a carbon-carbon unsaturated double bond include compounds represented by formula (3) or formula (4).
- X6 and X7 each independently represent a group represented by formula ( VI ), an acryloyl group or a methacryloyl group, and S3 and S4 each independently represent 0 to 20 Indicates an integer.
- the groups represented by formula (VI) in X 6 and X 7 are as described above.
- X 8 and X 9 each independently represent a group represented by formula (VI), an acryloyl group or a methacryloyl group, and S5 and S6 each independently represent 0 to 20 represents an integer, and Y 1 represents a C1-C6 alkylene group.
- the groups represented by formula (VI) in X8 and X9 are as described above. Examples of the “C1-C6 alkylene group” for Y 1 include methylene group, ethylene group, methylmethylene group, dimethylmethylene group and the like.
- the number average molecular weight (Mn) of the polyphenylene ether compound to be used is not particularly limited, but examples include 1,000 to 7,000, 1,000 to 5,000, 1,000 to 3,000.
- the number average molecular weight (Mn) is a value obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- the intrinsic viscosity of the polyphenylene ether compound used in the present invention can be 0.03 to 0.12 dl/g, 0.04 to 0.11 dl/g, 0.06 to 0.095 dl/g, and the like.
- Intrinsic viscosity is the intrinsic viscosity measured in methylene chloride at 25°C. More specifically, it is a value obtained by measuring a 0.18 g/45 ml methylene chloride solution (liquid temperature 25° C.) with a viscometer.
- polyphenylene ether compound used in the present invention a known one or a commercially available product can be used.
- commercially available products include SA90 (manufactured by SABIC), SA9000 (manufactured by SABIC) and OPE-2st (manufactured by Mitsubishi Gas Chemical Company).
- SA90 manufactured by SABIC
- SA9000 manufactured by SABIC
- OPE-2st manufactured by Mitsubishi Gas Chemical Company
- Polybutadiene in which the molar ratio of 1,2-bonded structure to 1,4-bonded structure is 80:20 to 100:0 (hereinafter also referred to as "(B-4) component")
- the polybutadiene used in the present invention has a 1,2 bond structure represented by formula (1) alone, or a 1,2 bond structure represented by formula (1) and a 1,4 bond structure represented by formula (2). Consists of a bond structure.
- the ratio of the 1,2-bonded structure represented by the formula (1) and the 1,4-bonded structure represented by the formula (2) contained in the polybutadiene is not particularly limited. ) is preferably from 80:20 to 100:0.
- the molecular weight of polybutadiene to be used is not particularly limited, but a weight average molecular weight (Mw) of 500 to 10,000, 500 to 8,000, 500 to 6,000, 500 to 5,000 can be selected.
- the weight average molecular weight (Mw) is a value obtained by converting data measured by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent based on the molecular weight of standard polystyrene.
- the polybutadiene may be a polybutadiene with a modified main chain and terminals, or may be a polybutadiene with an unmodified main chain and terminals.
- polybutadiene whose main chain and terminals are not modified from the viewpoint of obtaining a cured product having high insulating properties.
- a commercial item can be used as polybutadiene.
- Examples of commercially available polybutadiene include NISSO-PB B-1000 (manufactured by Nippon Soda Co., Ltd.), NISSO-PB B-2000 (manufactured by Nippon Soda Co., Ltd.), and NISSO-PB B-3000 (manufactured by Nippon Soda Co., Ltd.). ) and the like. These polybutadienes can be used singly or in combination of two or more.
- SBS styrene-butadiene-styrene block copolymer having a molar ratio of 1,2-bonded structure and 1,4-bonded structure in the butadiene block of 80:20 to 100:0
- (B-5 ) component styrene-butadiene-styrene block copolymer
- the styrene block is a polymerized block of styrene
- the butadiene block is a polymerized block of butadiene.
- the butadiene block is a 1,2-bonded structure represented by formula (1) only, or a 1,2-bonded structure represented by formula (1) and a 1,4-bonded structure represented by formula (2) Become.
- the molar ratio of the 1,2 bond structure represented by formula (1) and the 1,4 bond structure represented by formula (2) contained in the styrene-butadiene-styrene block copolymer used in the present invention is , 80:20 to 100:0.
- the weight ratio of the styrene block to the butadiene block in the styrene-butadiene-styrene block copolymer is not particularly limited, but is 10:90 to 80:20, 10:90 to 70:30, 10:90 to 60:40, 20:80-80:20, 30:70-80:20, 40:60-80:20 can be mentioned.
- the weight average molecular weight (Mw) of the styrene-butadiene-styrene block copolymer is not particularly limited, but examples include 2,000 to 100,000, 2,000 to 80,000, and 2,000 to 60,000. can be done.
- the molecular weight distribution (Mw/Mn) of the styrene-butadiene-styrene block copolymer is not particularly limited, but examples include 1.00 to 3.00, 1.00 to 2.00, and the like.
- the weight average molecular weight (Mw) and molecular weight distribution (Mw/Mn) are measured by gel permeation chromatography (GPC) using polystyrene as a standard substance.
- the measurement conditions were: mobile phase THF (tetrahydrofuran), mobile phase flow rate 1 mL/min, column temperature 40° C., sample injection amount 40 ⁇ L, sample concentration 2% by weight.
- the method for producing the styrene-butadiene-styrene block copolymer to be used is not particularly limited. For example, it can be produced by the methods described in JP-A-6-192502, JP-A-2000-514122, JP-A-2007-302901, WO2021/024679, and similar methods.
- a polymer having a repeating unit represented by formula (V) in the molecule (hereinafter also referred to as "(B-6) component")
- the resin composition of the present invention can contain a polymer having repeating units represented by formula (V) in the molecule.
- Z 3 represents a C6-C12 arylene group
- R 2 -R 7 each independently represent a hydrogen atom or a C1-C6 alkyl group.
- Examples of the “C6-C12 arylene group” for Z 3 include those exemplified for Z 4 .
- Examples of the “C1-C6 alkyl group” for R 2 to R 7 include the same groups as those exemplified for R 11 and R 12 .
- Formula (V) can specifically include formula (V-1).
- a polymer having a repeating unit represented by formula (V) in the molecule may be a polymer further having a structural unit represented by formula (5) in the molecule. Furthermore, it may have repeating units other than the repeating unit represented by formula (V) and the repeating unit represented by formula (5). That is, the polymer having the repeating unit represented by formula (V) in the molecule of component (B-6) includes the following polymers. I) a polymer comprising one or more repeating units represented by formula (V); II) one or more repeating units represented by formula (V); III) One or more repeating units represented by formula (V) and one repeating unit represented by formula (5) Alternatively, a polymer comprising two or more kinds and repeating units other than these. Among these polymers, the copolymer may be a random copolymer or a block copolymer.
- R 21 to R 23 each independently represent a hydrogen atom or a C1 to C6 alkyl group
- Ar 1 represents a C1 to C6 alkyl group-substituted or unsubstituted C6 to C12 aryl group.
- Examples of the “C1-C6 alkyl group” for R 21 to R 23 include the same groups as those exemplified for R 11 and R 12 .
- Examples of the “C6-C12 aryl group” for Ar 1 include a phenyl group, a naphthyl group, a biphenyl group, and the like.
- Examples of the “C1-C6 alkyl group” which is a substituent on Ar 1 include the same ones as those exemplified for R 11 and R 12 .
- formula (5) examples include formula (5-1) and formula (5-2).
- polymers having repeating units represented by formula (V) in the molecule include repeating units represented by formula (V-1) in the molecule and are represented by formula (5-1). and a polymer further comprising at least one of repeating units represented by formula (5-2).
- This polymer may be a block copolymer or a random copolymer.
- the weight average molecular weight of the polymer having repeating units represented by formula (V) in the molecule is preferably 1,200 to 40,000, more preferably 1,200 to 35,000.
- the weight average molecular weight is too high, there is a tendency for moldability and the like to deteriorate. Therefore, when the weight average molecular weight of the resin composition is within the above range, the heat resistance and moldability are excellent.
- the weight-average molecular weight may be one measured by general molecular weight measurement, and specifically includes a value measured using gel permeation chromatography (GPC).
- a polymer having the repeating unit represented by formula (V) in the molecule when the total of the repeating units in the polymer having the repeating unit represented by formula (V) in the molecule is 100 mol%, the above The molar content of repeating units represented by formula (V) is preferably 2 to 95 mol %, more preferably 8 to 81 mol %. Further, a polymer having a repeating unit represented by the formula (V) in the molecule is a polymer having the repeating unit represented by the formula (V) and the repeating unit represented by the formula (5) in the molecule.
- the molar content of the repeating unit represented by the formula (V) is preferably 2 to 95 mol%, more preferably 8 to 81 mol%, and the formula (5)
- the molar content of repeating units represented is preferably 5 to 98 mol %, more preferably 19 to 92 mol %.
- (meth)acrylate resin (hereinafter also referred to as "(B-7) component")
- (meth)acrylate resin a monofunctional (meth)acrylate monomer, (meth)acrylate oligomer, or the like can be used. Among them, it is preferable to contain a polyfunctional (meth)acrylate having two or more polymerizable unsaturated groups.
- a monofunctional (meth)acrylate monomer is a monomer having one (meth)acrylate group in the molecule, and includes alkyl (meth)acrylates, acrylates having an alicyclic hydrocarbon group, (meth)acrylates having an ether skeleton, There are (meth)acrylates having a cyclic ether skeleton, (meth)acrylates having an aromatic group, and the like.
- Alkyl (meth)acrylates include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, and t-butyl (meth)acrylate.
- (Meth)acrylates having an alicyclic hydrocarbon group include cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, isobornyl (Meth)acrylates and methoxylated cyclodecatriene (meth)acrylates.
- (Meth)acrylates having an ether skeleton include 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, and diethylene glycol monomethyl ether (meth)acrylate.
- Examples of (meth)acrylates having a cyclic ether skeleton include glycidyl (meth)acrylate, furfuryl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, 3-ethyl-3-oxetanylmethyl (meth)acrylate, (2-methyl- Ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, cyclic trimethylolpropane formal (meth)acrylate, ⁇ -butyrolactone (meth)acrylate, dioxolane (meth)acrylate, oxetane (meth)acrylate, (meth) ) acryloylmorpholine and the like.
- (Meth)acrylates having an aromatic group include phenyl (meth)acrylate, benzyl (meth)acrylate, methylbenzyl (meth)acrylate, ethylbenzyl (meth)acrylate, propylbenzyl (meth)acrylate, methoxybenzyl (meth)acrylate, Acrylate, phenoxyethyl (meth)acrylate, chlorobenzyl (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate and the like.
- Polyfunctional (meth)acrylates are compounds having two or more (meth)acrylate groups in the molecule, such as neopentyl glycol di(meth)acrylate, stearic acid-modified pentaerythritol di(meth)acrylate, dicyclopentenyl di(meth)acrylate, Acrylates, di(meth)acryloyl isocyanurate, alkylene oxide-modified bisphenol di(meth)acrylate, 2,2-bis(4-(meth)acryloxyphenyl)propane, 2,2-bis(4-(meth)acryloxy ethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxydiethoxyphenyl)propane, 2,2-bis(4-(meth)acryloxypropoxyphenyl)propane, 2,2-bis(4- Bifunctional (meth)acrylates such as (meth)acryloxytetraethoxyphenyl)propane, 2,2-bis(4-(meth
- (Meth)acrylate oligomers include, for example, urethane (meth)acrylate having a polybutadiene skeleton, urethane (meth)acrylate having a hydrogenated polybutadiene skeleton, urethane (meth)acrylate having a polycarbonate skeleton, urethane (meth)acrylate having a polyether skeleton, polyester Urethane (meth)acrylate with skeleton, urethane (meth)acrylate with castor oil skeleton, isoprene (meth)acrylate, hydrogenated isoprene (meth)acrylate, epoxy (meth)acrylate, (meth)acrylate oligomer with polyphenylene ether skeleton, etc. can give.
- (B-8) component) Vinyl resin (hereinafter also referred to as "(B-8) component")
- vinyl compounds include styrene and the like, trialkenyl isocyanurate compounds such as triallyl isocyanurate (TAIC), divinylbenzene, divinylbiphenyl, divinylnaphthalene, modified polyphenylene ether resins containing vinyl groups at both ends, all carbon -Polybutadiene having a total amount of 1 and 2 groups of 50% or more based on the total amount of carbon double bonds, and polybutadiene having a total amount of 1 and 2 groups of 50% or more based on the total amount of all carbon-carbon double bonds vinyl compounds (polyfunctional vinyl compounds) having two or more vinyl groups in the molecule, such as styrene-butadiene copolymers having Examples thereof include vinylbenzyl compounds having two or more vinylbenzyl groups in the molecule such as polydivinylbenzene resin and divinylbenzene-sty
- a compound having two or more unsaturated double bonds in the molecule and a compound having one unsaturated double bond in the molecule may be used in combination.
- Specific examples of compounds having one unsaturated double bond in the molecule include compounds having one vinyl group in the molecule (monovinyl compounds).
- thermosetting resin as component (B) is preferably at least one selected from (B-3) to (B-5).
- the resin composition of the present invention further contains a cross-linking agent. can be done.
- the cross-linking agent reacts with the unsaturated carbon bonds contained in the component (B) to form three-dimensional cross-links.
- Cross-linking agents include polyfunctional vinyl compounds such as divinylbenzene, divinylnaphthalene, and divinylbiphenyl; vinylbenzyl ether compounds synthesized from the reaction of phenol and vinylbenzyl chloride; styrene monomers, synthesized from the reaction of phenol and allyl chloride. allyl ether compounds; triallyl isocyanurates such as triallyl isocyanurate (TAIC (registered trademark)) and triallyl cyanurate (TAC); (meth)acrylate compounds (methacrylate and acrylate compounds) such as trimethylolpropane; Examples include compounds having an acenaphthylene skeleton. Heat resistance can be enhanced by using these cross-linking agents. Only one kind of crosslinking agent may be used, or two or more kinds thereof may be used.
- Examples of the compound having an acenaphthylene skeleton include acenaphthylene; Hydroxyacenaphthylene compounds such as 3-hydroxyacenaphthylene, 4-hydroxyacenaphthylene, 5-hydroxyacenaphthylene and 5,6-dihydroxyacenaphthylene; 3-methylacenaphthylene, 3-ethylacenaphthylene, 3-propylacenaphthylene, 4-methylacenaphthylene, 4-ethylacenaphthylene, 4-propylacenaphthylene, 5-methylacenaphthylene, 5 - Alkylacenaphthylene compounds such as ethylacenaphthylene, 5-propylacenaphthylene, 3,8-dimethylacenaphthylene, 5,6-dimethylacenaphthylene, 3-methoxyacenaphth
- the resin composition of the present invention may contain a polymerization initiator.
- Polymerization initiators used in the resin composition of the present invention include azo-based polymerization initiators and peroxide-based polymerization initiators.
- azo polymerization initiators include azobisisobutyronitrile, 1,1′-azobis(cyclohexane-1-carbonitrile), 2,2′-azobis ⁇ 2-methyl-N-[1,1 -bis(hydroxymethyl)ethyl]propionamide ⁇ , 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis[2-(hydroxymethyl)propionamide nitrile], 2,2′-azobis(2,4-dimethylvaleronitrile), 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile), dimethyl 2,2′-azobisisobutyrate, 2, 2′-azobis[2-(2-imidazolin-2-yl)propane], 2,2′-azobis ⁇ 2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide ⁇ and the like can be exemplified.
- Peroxide 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, 2, 2-bis(t-butylperoxy)octane, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, di(trimethylsilyl)per
- the polymerization initiator used in the resin composition of the present invention is preferably a peroxide-based polymerization initiator.
- composition ratio of resin composition When using epoxy resin (B-1) as component (B), the content of component (A) in the resin composition of the present invention is not particularly limited, but is 1 to 99% by weight with respect to the amount of component (B). %, 1 to 50% by weight, 1 to 30% by weight, and the like.
- the content of component (A) in the resin composition of the present invention is not particularly limited, but ( Examples include 1 to 99% by weight, 10 to 70% by weight, 10 to 50% by weight, etc., based on the total amount of component B) and the cross-linking agent.
- the content ratio of the component (B) and the cross-linking agent in the resin composition of the present invention is not particularly limited. 70, 90:10 to 50:50 and the like.
- the content of the polymerization initiator in the resin composition of the present invention is not particularly limited, but an amount of 0.1 to 10% by weight based on the total amount of the component (B) and the cross-linking agent is mentioned. be able to.
- the resin composition of the present invention may contain other components, if necessary, as long as the effects of the present invention are not impaired.
- Other components include organic solvents, thermoplastic resins, inorganic fillers, organic fillers, flame retardants, and other additives.
- organic solvents include amides, ethers, esters, aliphatic hydrocarbons, aromatic hydrocarbons, ketones, and organic halogen compounds.
- Amide organic solvents include N,N-dimethylformamide (DMF) and N,N-dimethylacetamide;
- ether organic solvents include diethyl ether, dipropyl ether, dibutyl ether, diamyl ether and tetrahydrofuran; ester solvents Ethyl acetate, propyl acetate, butyl acetate, amyl acetate, heptyl acetate, ethyl butyrate, isoamyl isovalerate, propylene glycol methyl ether acetate as the organic solvent of; normal hexane as the aliphatic hydrocarbon organic solvent, normal heptane, cyclohexane; aromatic hydrocarbon organic solvents such as toluene and xylene; ketone organic solvents such
- Thermoplastic resins include, for example, polyacrylate resin, polymethacrylate resin, polystyrene resin, polyphenylene ether resin, polyetherimide resin, polyether sulfone resin, polyphenylene sulfide resin, polycyclopentadiene resin, and polycyclopentadiene resin.
- Olefin resin polycycloolefin copolymer resin, polyarylate resin, polyether resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyimide resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, Polycarbonate resin, polyether ether ketone resin, polyester resin, liquid crystal polyester resin, fluorine resin, etc., and known thermoplastic elastomers such as styrene-ethylene-propylene copolymer, styrene-ethylene-butylene copolymer, styrene-butadiene Copolymer, styrene-isoprene copolymer, hydrogenated styrene-butadiene copolymer, hydrogenated styrene-isoprene copolymer, (meth)acrylonitrile-butadiene-(meth)acrylic acid cop
- Inorganic filler The material of the inorganic filler is not particularly limited, but examples include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, and hydrotal.
- boehmite aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, titanium Examples include bismuth oxide, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly suitable. As silica, spherical silica is preferable. An inorganic filler may be used individually by 1 type, and may be used in combination of 2 or more type.
- Inorganic fillers include aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, organosilazane compounds, titanate coupling agents, vinylsilane coupling agents, and methacryloxysilane. It is preferably treated with one or more surface treatment agents such as a base coupling agent, an acryloxysilane coupling agent, and a styrylsilane coupling agent.
- Organic fillers examples include rubber particles, fluororesin particles (fluoropolymer particles), polyamide fine particles, and silicone particles.
- fluororesin particles include polytetrafluoroethylene (PTFE), perfluoroalkoxyalkane (PFA), perfluoroethylenepropene copolymer (FEP), ethylene/tetrafluoroethylene copolymer (ETFE), tetrafluoroethylene fluoroethylene-perfluorodioxole copolymer (TFE/PDD), polyvinylidene fluoride (PVDF), polychlorotrifluoroethylene (PCTFE), ethylene-chlorotrifluoroethylene copolymer (ECTFE), polyvinyl fluoride (PVF). be done. These resins may be used individually by 1 type, and may be used in combination of 2 or more type.
- fluororesin particles fluoropolymer particles
- PTFE particles which are commercially available fluorine-based polymer particles, include "Lubron (registered trademark) L-2" manufactured by Daikin Industries, Ltd., “Lubron L-5" manufactured by Daikin Industries, Ltd., Daikin Industries, Ltd. ) manufactured by "Lubron L-5F", manufactured by Asahi Glass Co., Ltd. "Fluon (registered trademark) PTFE L-170JE” manufactured by Asahi Glass Co., Ltd. "Fluon PTFE L-172JE” manufactured by Asahi Glass Co., Ltd.
- Surface treatment includes, for example, surface treatment with a surface treatment agent.
- the surface treatment agent is not particularly limited.
- Surface treatment agents include surfactants such as nonionic surfactants, amphoteric surfactants, cationic surfactants and anionic surfactants, as well as inorganic fine particles. From the viewpoint of affinity, it is preferable to use a fluorine-based surfactant as the surface treatment agent.
- fluorine-based surfactants include "Surflon (registered trademark) S-243" (perfluoroalkyl ethylene oxide adduct) manufactured by AGC Seimi Chemical Co., Ltd., and "Megafac (registered trademark)” manufactured by DIC Corporation.
- Neos Corporation F-251
- DIC Corporation Megafac F-477
- DIC Corporation Megafac F-553
- DIC Corporation Megafac R-40
- DIC Corporation Megafac R-43
- DIC Corporation Megafac R-94
- Neos Corporation FTX-218
- Neos Corporation Ftergent (registered trademark) 610FM
- Neos Corporation Ftergent 730LM
- the flame retardant is not particularly limited, but known flame retardants can be used. Specifically, in the field of using halogen-based flame retardants such as brominated flame retardants, for example, ethylene dipentabromobenzene, ethylenebistetrabromoimide, decabromodiphenyl oxide, and tetradecabromo, which have a melting point of 300° C. or higher Diphenoxybenzene is preferred.
- halogen-based flame retardants such as brominated flame retardants, for example, ethylene dipentabromobenzene, ethylenebistetrabromoimide, decabromodiphenyl oxide, and tetradecabromo, which have a melting point of 300° C. or higher Diphenoxybenzene is preferred.
- a halogen-based flame retardant By using a halogen-based flame retardant, desorption of halogen at high temperatures can be suppressed, and it is thought that a decrease in heat resistance can be suppressed.
- phosphorus-based flame retardants such as phosphate-based flame retardants, phosphazene-based flame retardants, and phosphinate-based flame retardants can be used.
- phosphate flame retardant include condensed phosphate of dixylenyl phosphate.
- phosphazene-based flame retardant is phenoxyphosphazene.
- phosphinate-based flame retardants include metal phosphinates of aluminum dialkylphosphinates. Each of the exemplified flame retardants may be used alone, or two or more of them may be used in combination.
- additives include antifoaming agents such as silicone antifoaming agents and acrylate ester antifoaming agents, organic metal compounds such as organic copper compounds, organic zinc compounds and organic cobalt compounds, and leveling.
- Adhesion agents such as silane coupling agents, tackifiers such as tackifiers, heat stabilizers, antistatic agents, storage stabilizers such as BHT, antioxidants, light stabilizers, UV absorbers, dyes and pigments , lubricants, wetting and dispersing agents, heavy metal deactivators, ion trapping agents, emulsifiers, water dispersion stabilizers, release agents, waxes, rheology control agents, surfactants and the like.
- the resin composition of the present invention can be used as a solder resist, an underfill material, a die bonding material, a semiconductor sealing material, a hole-filling resin, a part-embedding resin, an insulating material for a printed wiring board, etc. It can be used in a wide range of applications where the composition is required.
- the resin composition of the present invention is preferably a resin composition for insulating layers of printed wiring boards. Printed wiring boards include single-sided printed boards, double-sided printed boards, multilayer printed boards, flexible printed boards, build-up boards, and the like.
- the form of the resin composition of the present invention is not particularly limited, but it can be applied to adhesive films, sheet-like laminated materials such as prepreg, and printed wiring boards.
- the resin composition of the present invention can be applied to a printed wiring board in the form of a varnish to form an insulating layer. used for
- a cured product obtained by curing the resin composition of the present invention can be used as a molded product, an insulator for a printed wiring board, a laminate with a metal foil, a cast product, an adhesive, a coating film, and a film.
- a cured product of a semiconductor encapsulating material is a cast or molded product, and methods for obtaining a cured product for such applications include casting a curable resin composition, or using a transfer molding machine, an injection molding machine, or the like.
- a cured product can be obtained by molding using the resin and heating at 80 to 230° C. for 0.5 to 10 hours.
- Resin varnish The resin composition of the present invention is used for the purpose of impregnating a base material (fibrous base material) for forming a prepreg, for coating a support film for forming an adhesive film, or for forming a printed wiring board. It can be prepared as a varnish for the purpose of making it a resin varnish. This resin varnish is particularly suitable for printed wiring boards and can be used as a varnish for printed wiring boards.
- a resin varnish is prepared, for example, as follows. Each component is put into an organic solvent and dissolved. At this time, it may be heated, if necessary. After that, if necessary, a component that does not dissolve in an organic solvent such as an inorganic filler is added and dispersed using a ball mill, a bead mill, a planetary mixer, a roll mill, or the like to obtain a varnish-like curable resin composition. is prepared.
- Materials for electronic parts especially high-frequency electronic parts, which are excellent by incorporating inorganic high-dielectric powders such as barium titanate or inorganic magnetic substances such as ferrite into curable resin compositions or resin varnishes. becomes.
- Sheet-like laminated material The resin composition of the present invention can be used for sheet-like laminated material.
- sheet-like laminate materials include prepregs and adhesive films.
- the prepreg of the present invention is characterized by having a substrate impregnated with the resin composition of the present invention.
- the substrate include fibrous substrates such as glass cloth, aramid cloth, polyester cloth, glass nonwoven fabric, aramid nonwoven fabric, polyester nonwoven fabric, pulp paper, and linter paper.
- the prepreg of the present invention can be produced by a known method. For example, there is a method of impregnating a substrate with the resin varnish of the present invention and then drying the substrate.
- a semi-cured (B stage) prepreg can be obtained by heating the substrate impregnated with the resin varnish under desired heating conditions, for example, at 80 to 170° C. for 1 to 10 minutes to remove the solvent. .
- the adhesive film of the present invention is characterized by having a resin composition layer containing the resin composition of the present invention on a support film.
- the adhesive film of the invention can be produced by a known method.
- the resin varnish of the present invention can be produced by applying the resin varnish of the present invention to a support film using a die coder or the like, and then drying the organic solvent by heating or blowing hot air to form a resin composition layer. can.
- the resin composition layer is dried so that the content of the organic solvent is 10% by mass or less, preferably 5% by mass or less.
- a resin composition layer is formed by drying a varnish containing 30 to 60% by mass of organic solvent at 50 to 150° C. for about 3 to 10 minutes. can do.
- the thickness of the resin composition layer formed in the adhesive film is preferably equal to or greater than the thickness of the conductor layer. Since the thickness of the conductor layer of the circuit board is usually in the range of 5 to 70 ⁇ m, the resin composition layer preferably has a thickness of 10 to 100 ⁇ m. From the viewpoint of thinning, the thickness is more preferably 15 to 80 ⁇ m.
- Support films include polyolefin films such as polyethylene, polypropylene, and polyvinyl chloride, polyethylene terephthalate (hereinafter sometimes abbreviated as "PET"), polyester films such as polyethylene naphthalate, polycarbonate films, and polyimide films.
- PET polyethylene terephthalate
- polyester films such as polyethylene naphthalate, polycarbonate films, and polyimide films.
- release paper metal foil, such as copper foil and aluminum foil.
- a plastic film is preferable, and a polyethylene terephthalate film is more preferable, from the viewpoint of versatility.
- the support and the protective film described later may be subjected to surface treatment such as mud treatment and corona treatment.
- a mold release treatment may be performed with a mold release agent such as a silicone resin mold release agent, an alkyd resin mold release agent, or a fluororesin mold release agent.
- the thickness of the support film is not particularly limited, it is preferably 10-150 ⁇ m, more preferably 25-50 ⁇ m.
- a protective film conforming to the support can be further laminated on the surface of the resin composition layer to which the support is not in close contact.
- the thickness of the protective film is not particularly limited, it is, for example, 1 to 40 ⁇ m. By laminating the protective film, it is possible to prevent dust from adhering to the surface of the resin composition layer and scratches on the surface of the resin composition layer.
- the adhesive film can also be wound up in a roll and stored.
- the printed wiring board insulator of the present invention comprises a cured product of either the prepreg of the present invention or the adhesive film of the present invention.
- the method for producing the printed wiring board insulator of the present invention is not particularly limited, but an example thereof includes a method of stacking one or more sheet-like laminate materials and subjecting them to heating and pressure molding.
- the printed wiring board insulator of the present invention is suitable as an insulating layer for single-sided printed boards, double-sided printed boards, multilayer printed boards, flexible printed boards, and build-up boards.
- the laminate with metal foil of the present invention comprises a layer of the printed wiring board insulator 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.
- the sheet-like laminate material of the present invention described above and a metal foil are laminated in a layer configuration according to the purpose, and each layer is laminated under heat and pressure.
- a method of heat curing at the same time as bonding can be mentioned.
- the laminate with a metal foil of the present invention the printed wiring board insulator 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. In addition to the above, it is also possible to repeat lamination and curing a plurality of 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.
- the resin composition of the present invention can also be used as an adhesive. The laminate molding and curing described above can be performed under the same conditions as in the production of the printed wiring board insulator of the present invention.
- the resin composition containing the polymer of the present invention can be processed into a molding material, a sheet or a film, and has properties such as low dielectric constant, low water absorption, and high heat resistance in fields such as the electrical industry, space/aircraft industry, and automobiles. It can be used for low dielectric materials, insulating materials, heat-resistant materials, structural materials, etc. that can satisfy the characteristics. In particular, it can be used as a single-sided, double-sided, multilayer printed circuit board, flexible printed circuit board, build-up circuit board, and the like.
- semiconductor-related materials or optical materials paints, photosensitive materials, adhesives, sewage treatment agents, heavy metal scavengers, ion exchange resins, antistatic agents, antioxidants, antifogging agents, antirust agents , antifouling agents, disinfectants, insect repellents, medical materials, flocculants, surfactants, lubricants, solid fuel binders, conductive agents, resin modifiers, asphalt modifier plasticizers, sintering binders, etc. can be applied.
- the polymer of the present invention is a resin having a low dielectric constant and a low dielectric loss tangent, a high glass transition point, high solubility in organic solvents, and high compatibility with thermosetting resins. Therefore, in fields such as the electrical/electronics industry and the space/aircraft industry, molding defects such as warpage are required in recent years as dielectric materials, insulating materials, heat-resistant materials, structural materials, etc., in response to the strong demand for smaller and thinner products. A phenomenon-free cured molding can be provided. Furthermore, it is possible to realize a highly reliable curable resin composition, a cured product, or a material containing the same, due to excellent wiring embedding flatness and adhesion to different materials. Examples are shown below, but the technical scope of the present invention is not limited to the examples.
- Example 1 Synthesis of N,N-bis(4-(tert-butyl)phenyl)acrylamide Bis(4-tert-butylphenyl)amine (100 g, 0.355 mol), N,N-dimethylaniline (64.59 g, 0.533 mol), and 400 mL of ultra-dehydrated toluene are placed in a nitrogen-substituted 1 L four-necked flask. was charged and stirred until uniformly dissolved. Next, the reaction solution was cooled to 0° C. or below with an ice/ethanol bath, acrylic acid chloride (38.59 g, 0.426 mol) was slowly added dropwise, and the mixture was stirred for 30 minutes.
- acrylic acid chloride 38.59 g, 0.426 mol
- reaction solution was heated to room temperature and reacted for 24 hours.
- reaction mixture was washed with 1N aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and brine.
- the organic layer was dehydrated with magnesium sulfate, and then the filtrate was distilled off with an evaporator.
- the resulting crude product was purified by recrystallization with hexane to obtain N,N-bis(4-(tert-butyl)phenyl)acrylamide (92.90 g, yield 79%).
- the polyacrylamide of the present invention has excellent heat resistance and dielectric properties, can be dissolved in organic solvents at high concentrations, and is compatible with other thermoplastic resins and thermosetting resins. It turns out that it is excellent in solubility.
- Example 3 Each reagent having the composition (parts by weight) shown in Table 2 was added to toluene and mixed so that the solid content concentration was 50% by weight. After that, toluene was removed from the obtained liquid by an evaporator to obtain a powdery resin composition. The resin composition was cured by hot pressing at 200° C. for 90 minutes. The physical properties of the obtained cured product were measured for the following items, and the results are shown in Table 2.
- Tg Glass transition temperature
- DSC differential scanning calorimetry
- Df dielectric loss tangent test
- Example 4 Each reagent having the composition (parts by weight) shown in Table 3 was added to toluene and mixed so that the solid content concentration was 50% by weight. After that, toluene was removed from the obtained liquid by an evaporator to obtain a powdery resin composition. The resin composition was cured by hot pressing at 200° C. for 120 minutes. The physical properties of the obtained cured product were measured for the following items, and the results are shown in Table 3.
- Tg Glass transition temperature
- DSC differential scanning calorimetry
- Df dielectric loss tangent test
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Abstract
Description
本願は、2021年7月14日に出願された日本国特許出願第2021-116330号および2022年6月2日に出願された日本国特許出願第2022-90373号に対し優先権を主張し、その内容をここに援用する。
近年、上記ネットワーク関連電子機器では、大容量の情報を低損失かつ高速で伝送・処理する必要があり、それら製品のプリント配線板で扱う電気信号も高周波化が進んでいる。高周波の電気信号は減衰しやすいため、プリント配線板における伝送損失を一層低くする必要がある。そのため、プリント配線板を製造する際に用いられる樹脂には、低誘電率且つ低誘電正接であることが求められる。
本発明は、低誘電率且つ低誘電正接であり、かつガラス転移点が高く、有機溶媒に対する高い溶解性と熱硬化性樹脂に対する高い相溶性を示すポリマーおよびそれを含む樹脂組成物とその成形体を提供することを目的とする。
(1)式(I)で表される重合性化合物由来の繰り返し単位の少なくとも1種を有するポリマー。
(式中、X1、X2は、それぞれ独立に、C3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基又はC3~C6環状アルコキシ基を表し、nは0又は1を表し、Z1、Z2は、それぞれ独立に、単結合又はC1~C3アルキレン基を表し、各Rは、それぞれ独立に、有機基又はハロゲノ基を表し、m1、m2は、それぞれ独立に、0~4いずれかの整数を表し、Yは、重合可能な官能基を表す。)
(2)Yが、アクリロイル基またはメタクリロイル基である、(1)に記載のポリマー。
(3)(1)に記載のポリマーを含有する樹脂組成物。
(4)更に、(1)に記載のポリマー以外の樹脂を含有する、(3)に記載の樹脂組成物。
(5)(1)に記載のポリマー以外の樹脂が熱硬化性樹脂である、(4)に記載の樹脂組成物。
(6)熱硬化性樹脂がエポキシ樹脂である、(5)に記載の樹脂組成物。
(7)更に、硬化剤として活性エステル系化合物を含有する、(6)に記載の樹脂組成物。
(8)熱硬化性樹脂が、
マレイミド基を一つ以上有するマレイミド化合物、
ポリフェニレンエーテル化合物、
1,2結合構造と1,4結合構造のモル比が80:20~100:0であるポリブタジエン、
ブタジエンブロック中の1,2結合構造と1,4結合構造のモル比が80:20~100:0であるスチレン-ブタジエン-スチレンブロック共重合体(SBS)、及び
分子中に式(V)
(式(V)中、Z3は、C6~C12アリーレン基を示し、R2~R7は、それぞれ独立に、水素原子又はC1~C6アルキル基を示す。)で表される繰り返し単位を有する重合体から選択される少なくとも1種以上である、(5)に記載の樹脂組成物。
(9)ポリフェニレンエーテル化合物が、式(VI)で表される基、アクリロイル基又はメタクリロイル基により末端変性されたポリフェニレンエーテル化合物である、(8)に記載の樹脂組成物。
(式(VI)中、*は、結合位置を示し、pは、0~10の整数を示し、Z4は、C6~C12アリーレン基を示し、R8~R10は、それぞれ独立に、水素原子又はC1~C6アルキル基を示す。)
(10)(3)~(9)のいずれかに記載の樹脂組成物の硬化物を用いた、成形体。
(11)プリント配線板の絶縁層用樹脂組成物である、(3)~(9)のいずれかに記載の樹脂組成物。
(12)(3)~(9)のいずれかに記載の樹脂組成物を含有する樹脂ワニス。
(13)(3)~(9)のいずれかに記載の樹脂組成物が基材に含侵されたプリプレグ。
(14)(3)~(9)のいずれかに記載の樹脂組成物を含有する樹脂組成物層を支持フィルム上に有することを特徴とする、接着フィルム。
(15)(13)に記載のプリプレグの硬化物よりなるプリント配線板用絶縁体。
(16)(14)に記載の接着フィルムの硬化物よりなるプリント配線板用絶縁体。
(17)(15)に記載のプリント配線板用絶縁体からなる層と金属箔からなる層とを備える金属箔付き積層物。
(18)(16)に記載のプリント配線板用絶縁体からなる層と金属箔からなる層とを備える金属箔付き積層物。
(19)式(III)で表される化合物。
(式中、X1、X2は、それぞれ独立に、C3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基又はC3~C6環状アルコキシ基を表し、nは0又は1を表し、Z1、Z2は、それぞれ独立に、単結合又はC1~C3アルキレン基を表し、各Rは、それぞれ独立に、有機基又はハロゲノ基を表し、m1、m2は、それぞれ独立に、0~4いずれかの整数を表し、Yは、重合可能な官能基を表す。)
(20)式(III)で表される化合物が、式(IV)で表される化合物である、(19)に記載の化合物。
(式中、R1は水素原子又はメチル基を示す)
X1、X2は、それぞれ独立に、C3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基又はC3~C6環状アルコキシ基を表す。
X1及びX2における、「C3~C6環状アルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。
X1及びX2における、「C3~C6分岐アルコキシ基」としては、イソプロピルオキシ基、sec-ブチルオキシ基、イソブチルオキシ基、tert-ブチルオキシ基、ネオペンチルオキシ基、イソペンチルオキシ基、sec-ペンチルオキシ基、1-エチルプロピル基オキシ基、tert-ペンチルオキシ基、イソヘキシルオキシ基、3-メチルペンチルオキシ基、2,2-ジメチルブチルオキシ基、2,3-ジメチルブチルオキシ基等が挙げられる。
X1及びX2における、「C3~C6環状アルコキシ基」としては、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基、シクロヘキシルオキシ基等が挙げられる。
nは、1であることが好ましい。
Z1、Z2におけるC1~C3アルキレン基としては、メチレン、エチレン、プロパン-1,3-ジイル等が挙げられる。
「有機基」としては、化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。有機基としては、メチル基、エチル基、n-プロピル基、I-プロピル基、n-ブチル基、s-ブチル基、I-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基などのC1~6アルキル基や、フェニル基、ナフチル基などのC6~10アリール基や、メトキシ基、エトキシ基、n-プロポキシ基、I-プロポキシ基、n-ブトキシ基、s-ブトキシ基、I-ブトキシ基、t-ブトキシ基などのC1~6アルコキシ基や、クロロメチル基、クロロエチル基、トリフルオロメチル基、1,2-ジクロロ-n-プロピル基、1-フルオロ-n-ブチル基、パーフルオロ-n-ペンチル基などのC1~6ハロアルキル基等が挙げられる。
「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基が挙げられる。
m1及びm2は、0であることが好ましい。
本発明においては、Yとしては、アクリロイル基、メタクリロイル基が好ましく、アクリロイル基がより好ましい。
式(II)中、Y、Z1、Z2、X1、R、m1、m2は、式(I)において説明したものと同じものである。
式(II)中、X3は、C3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基、C3~C6環状アルコキシ基、水素原子、有機基又はハロゲノ基を表し、これらのうち、C3~C6分岐アルキル基、C3~C6環状アルキル基又はC3~C6分岐アルコキシ基が好ましく、C3~C6分岐アルキル基がより好ましく、tert-ブチル基が特に好ましい。X3におけるC3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基、C3~C6環状アルコキシ基は、式(I)中のX1、X2におけるC3~C6分岐アルキル基、C3~C6環状アルキル基、C3~C6分岐アルコキシ基、C3~C6環状アルコキシ基と同じものを挙げることができる。
(式(I)中、各記号は上記のとおりである。)
すなわち、本発明で使用するポリマーは、具体的には、以下のポリマ-を包含する。
I)式(I)で表される重合性化合物由来の繰り返し単位の1種からなるホモポリマー、
II)式(I)で表される重合性化合物由来の繰り返し単位の2種以上からなるコポリマー、
III)式(I)で表される重合性化合物由来の繰り返し単位の少なくとも1種と、他のラジカル重合性化合物由来の繰り返し単位の少なくとも1種とからなるコポリマー、及び
IV)式(I)で表される重合性化合物由来の繰り返し単位の2種以上と、他のラジカル重合性化合物由来の繰り返し単位の少なくとも1種とからなるコポリマー。
式(I)で表される重合性化合物由来の繰り返し単位を有するポリマーは、I)式(I)で表される重合性化合物由来の繰り返し単位の1種からなるホモポリマー、またはIII)式(I)で表される重合性化合物由来の繰り返し単位の少なくとも1種と、他のラジカル重合性化合物由来の繰り返し単位の少なくとも1種とからなるコポリマーであることが好ましく、I)式(I)で表される重合性化合物由来の繰り返し単位の1種からなるホモポリマーであることがより好ましい。
上記ポリマーのうち、II)~IV)のコポリマーは、各繰り返し単位が、ランダム配列されているもの、交互配列されているもの、ブロック配列されているもののいずれでもよい。
また、本発明のコポリマーの場合は、分子鎖が、直鎖であってもよいし、分岐鎖であってもよい。分岐鎖は、一点で分岐してなる分岐鎖(スター型)、複数点で分岐してなる分岐鎖(グラフト型)などが挙げられる。
また、本発明に係るポリマーの分子量分布(PDI)は、重量平均分子量/数平均分子量(Mw/Mn)の比で、好ましくは1.0~5.0、より好ましくは1.0~4.0、最も好ましくは1.0~3.0である。
なお、重量平均分子量及び数平均分子量は、THFを溶媒とするゲルパーミエーションクロマトグラフィ(GPC)にて測定したデータを、標準として使用するポリメタクリル酸メチルの分子量に基づいて換算した値である。
「他のラジカル重合性化合物」とは、式(I)で表される化合物以外のラジカル重合性化合物であり、融点、粘度又は屈折率などの目的とする物性に応じて適宜選定すればよく、特に限定されるものではないが、(メタ)アクリル酸類、(メタ)アクリロニトリル、スチレン類、ビニル系化合物、オレフィン化合物、不飽和カルボン酸無水物等が挙げられ、これらの1種又は2種以上を使用することができる。具体的には、成分(1)ラジカル重合性化合物において例示されたものと同様の化合物が挙げられる。
なお、本発明において、「(メタ)アクリル」は、「アクリル」及び/又は「メタクリル」を意味する。
特に、「他のラジカル重合性化合物」としては、(メタ)アクリレート、(メタ)アクリルアミド等の(メタ)アクリル酸類、不飽和ジカルボン酸無水物、スチレン類が好ましい。
脂環式炭化水素基を有する(メタ)アクリレートとしては、シクロヘキシル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンテニル(メタ)アクリレート、ジシクロペンテニロキシエチル(メタ)アクリレート、イソボルニル(メタ)アクリレート、メトキシ化シクロデカトリエン(メタ)アクリレートが挙げられる。
エーテル骨格を有する(メタ)アクリレートとしては、2-メトキシエチル(メタ)アクリレート、2-エトキシエチル(メタ)アクリレート、ジエチレングリコールモノメチルエーテル(メタ)アクリレートが挙げられる。
環状エーテル骨格を有する(メタ)アクリレートとしては、グリシジル(メタ)アクリレート、フルフリル(メタ)アクリレート、テトラヒドロフルフリル(メタ)アクリレート、3-エチル-3-オキセタニルメチル(メタ)アクリレート、(2-メチル-エチル-1,3-ジオキソラン-4-イル)メチル(メタ)アクリレート、環状トリメチロールプロパンホルマール(メタ)アクリレート、γ-ブチロラクトン(メタ)アクリレート、ジオキソラン(メタ)アクリレート、オキセタン(メタ)アクリレート、(メタ)アクリロイルモルフォリン等が挙げられる。
芳香族基を有する(メタ)アクリレートとしては、フェニル(メタ)アクリレート、ベンジル(メタ)アクリレート、メチルベンジル(メタ)アクリレート、エチルベンジル(メタ)アクリレート、プロピルベンジル(メタ)アクリレート、メトキシベンジル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、クロロベンジル(メタ)アクリレート、ノニルフェノキシポリエチレングリコール(メタ)アクリレート等が挙げられる。
不飽和ジカルボン酸無水物としては、マレイン酸無水物、シトラコン酸無水物、イタコン酸無水物等が挙げられる。
スチレン類としては、スチレン、p-ヒドロキシスチレン、p-クロロスチレン、p-ブロモスチレン、p-メチルスチレン、p-メトキシスチレン、p-t-ブトキシスチレン、p-t-ブトキシカルボニルスチレン等が挙げられる。
その他としては、酢酸ビニル、塩化ビニル、塩化ビニリデン、(メタ)アクリロニトリル、ビニルエーテル、アクロレイン、ジビニルベンゼン等のビニル化合物;エチレン、プロピレン、ブタジエン等のオレフィン化合物等が挙げられる。
本発明に用いるポリマー中、式(I)で表される重合性化合物由来の繰り返し単位と、他のラジカル重合異性化合物由来の繰り返し単位の含有量は、本発明の効果を示す限り、特に制限されない。式(I)で表される重合性化合物由来の繰り返し単位と、他のラジカル重合異性化合物由来の繰り返し単位は、重量比で、99.5:0.5~0.5:99.5、99.5:0.5~30:70、99:1~30:70、90:10~30:70、60:40~30:70等の範囲を選択することができる。
本発明に用いる重合性化合物である式(I)で表される化合物は、実施例の方法や他の公知の方法により合成することができる。
たとえば、式(I)のYがアクリル基又はメタクリル基の場合は、以下の方法により製造することができる。
(式中、X1、X2、n、Z1、Z2、R、m1、m2は、式(I)における定義と同じである。)
式(I’)で表される第2級アミンと(メタ)アクリル酸クロライド等の(メタ)アクリル酸ハライドとを、溶媒中、塩基の存在下で反応させる。
溶媒としては、N,N-ジメチルホルムアミド(DMF)、N,N-ジメチルアセトアミド等のアミド系溶媒、テトラヒドロフラン(THF)、1,2-ジメトキシエタン、ジエチルエーテル、メチルセルソルブ等のエーテル系溶媒、ベンゼン、トルエン、キシレン、クロルベンゼン、ジクロロベンゼン、ベンゾニトリル等の芳香族炭化水素、ペンタン、ヘキサン、オクタン、シクロヘキサン等の飽和炭化水素、ジクロロメタン、クロロホルム、四塩化炭素、1,2-ジクロロエタン等のハロゲン化炭化水素、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン系溶媒、酢酸エチル、酢酸ブチル、酢酸2-メトキシ-1-メチルエチル等のエステル系溶媒等が挙げられ、これらの1種又は2種以上の混合溶媒を使用することができる。
塩基としては、トリエチルアミン、トリブチルアミン等の脂肪族アミン、ピリジン、N-エチルピリジン、N,N-ジメチルアニリン、N,N-ジメチルアミノピリジン等の芳香族アミン、ナトリウムエチラート、ナトリムメチラート等の金属アルコキシド等の有機塩基や、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、水酸化カルシウム、水酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム、炭酸水素ナトリウム等のアルカリ金属又はアルカリ土類金属の水酸化物、アルカリ金属又はアルカリ土類金属の炭酸塩等の無機塩基を用いることができる。
反応温度は、-50℃~200℃である。
本発明に用いるポリマーは、式(I)で表される重合性化合物の少なくとも1種を重合、又は当該化合物と他の重合性化合物とを重合したものであれば、特に制限なく使用することができる。重合反応は、特に制限されず、ポリアクリレート等を合成する公知の方法であってもよく、例えば、ラジカル重合、アニオン重合、カチオン重合、開環重合、配位重合等を挙げることができる。実施例にその一例を示す。
たとえば、式(I)のYがアクリル基又はメタクリル基である化合物と(メタ)アクリレートをラジカル重合する場合は、式(I)で表される重合性化合物と(メタ)アクリレートを溶媒中で、ラジカル重合開始剤の存在下で、加熱又は光照射して重合反応を行う。
重合溶媒は、重合反応に関与せず、かつ重合体と相溶性のある溶媒であれば特に制限されず、具体的には、ジエチルエーテル、テトラヒドロフラン(THF)、ジオキサン、トリオキサンなどのエーテル系化合物や、酢酸エチルなどのエステル系化合物や、メチルエチルケトンやシクロヘキサノンなどのケトン系化合物や、ヘキサンやトルエンなどの脂肪族、芳香族又は脂環式炭化水素化合物などの非極性溶媒又は低極性溶媒を例示することができる。これらの溶媒は、1種単独で、又は2種以上の混合溶媒として用いることができる。
ラジカル重合開始剤としては、たとえば、アゾビスイソブチロニトリル、アゾビス-2,4-ジメチルバレロニトリル、アゾビスシクロヘキサンカルボニトリル、アゾビス-2-アミジノプロパン・塩酸塩、ペルオキソ二硫酸カリウム、ペルオキソ二硫酸アンモニウム、t-ブチルヒドロペルオキシド、過酸化ジ-t-ブチルクメンヒドロペルオキシド、過酸化アセチル、過酸化ベンゾイル、過酸化ラウロイルなどが挙げられる。
本発明の樹脂組成物は、上記の式(I)で表される重合性化合物由来の繰り返し単位の少なくとも1種からなるポリマー(以下、「(A)成分」ともいう)を含有する。
本発明の樹脂組成物は、更に、(A)成分以外の成分として、電離放射線硬化性樹脂や熱硬化性樹脂などの硬化性樹脂(以下、「(B)成分」ともいう)やその他の成分を含有することができる。
(1)硬化性樹脂
硬化性樹脂としては、(メタ)アクリル系樹脂、ビニル系樹脂、アリル系樹脂、メラミン系樹脂、ウレタン系樹脂、エポキシ系樹脂、シリコーン系樹脂、ポリエステル系樹脂、ポリアミド酸系樹脂、ポリイミド系樹脂、スチレンマレイン酸系樹脂、スチレン無水マレイン酸系樹脂、マレイミド系樹脂、シアネート系樹脂などを使用することができる。ここで、「電離放射線硬化性樹脂」とは、赤外線、可視光線、紫外線、X線、電子線などのすべての電磁波を包含する電離放射線のいずれかの照射により硬化する樹脂をいう。
以下に、本発明の樹脂組成物として用いられる熱硬化性樹脂の例を具体的に説明する。
エポキシ樹脂としては、例えば、ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビスフェノールAF型エポキシ樹脂、ジシクロペンタジエン型エポキシ樹脂、トリスフェノール型エポキシ樹脂、ナフトールノボラック型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、エステル骨格を有する脂環式エポキシ樹脂、tert-ブチル-カテコール型エポキシ樹脂、ナフタレン型エポキシ樹脂、ナフトール型エポキシ樹脂、アントラセン型エポキシ樹脂、グリシジルアミン型エポキシ樹脂、グリシジルエステル型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ビフェニル型エポキシ樹脂、線状脂肪族エポキシ樹脂、ブタジエン構造を有するエポキシ樹脂、脂環式エポキシ樹脂、複素環式エポキシ樹脂、スピロ環含有エポキシ樹脂、シクロヘキサンジメタノール型エポキシ樹脂、ナフチレンエーテル型エポキシ樹脂、トリメチロール型エポキシ樹脂、テトラフェニルエタン型エポキシ樹脂等が挙げられる。エポキシ樹脂は1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
(B)成分である熱硬化性樹脂として、上記(B-1)を用いる場合、硬化剤を含有させることができる。
エポキシ樹脂の硬化剤としては、特に限定されないが、フェノール系硬化剤、ナフトール系硬化剤、活性エステル系硬化剤、ベンゾオキサジン系硬化剤、シアネートエステル系硬化剤、酸無水物系硬化剤等が挙げられ、誘電正接を低下させるという観点から、シアネートエステル系硬化剤、活性エステル系硬化剤が好ましい。これらは1種又は2種以上組み合わせて使用してもよい。
さらに硬化促進剤を含有させることにより、エポキシ樹脂と硬化剤を効率的に硬化させることができる。硬化促進剤としては、特に限定されないが、アミン系硬化促進剤、グアニジン系硬化促進剤、イミダゾール系硬化促進剤、金属系硬化促進剤、ホスホニウム系硬化促進剤等が挙げられる。これらは1種又は2種以上組み合わせて使用してもよい。
ホスホニウムボレート化合物、テトラフェニルホスホニウムテトラフェニルボレート、n-ブチルホスホニウムテトラフェニルボレート等の有機ホスフィン類と有機ボロン類との錯体;(4-メチルフェニル)トリフェニルホスホニウムチオシアネート、テトラフェニルホスホニウムチオシアネート、ブチルトリフェニルホスホニウムチオシアネート、テトラブチルホスホニウムデカン酸塩等の芳香族ホスホニウム塩及び第三級ホスフィンとキノン類との付加物などが挙げられる。
第三級ホスフィンとしては、特に限定されないが、例えば、トリ-n-ブチルホスフィン、ジブチルフェニルホスフィン、ブチルジフェニルホスフィン、エチルジフェニルホスフィン、トリフェニルホスフィン、トリス(4-メチルフェニル)ホスフィン、トリス(4-メトキシフェニル)ホスフィン等が挙げられる。また、キノン類としては、例えば、o-ベンゾキノン、p-ベンゾキノン、ジフェノキノン、1,4-ナフトキノン、アントラキノン等が挙げられる。これらは1種又は2種以上組み合わせて使用してもよい。
本発明に用いるマレイミド化合物は、分子中に一個以上のマレイミド基を有する化合物であれば、特に限定されるものではない。その具体例としては、例えば、N-フェニルマレイミド、N-ヒドロキシフェニルマレイミド、ビス(4-マレイミドフェニル)メタン、2,2-ビス{4-(4-マレイミドフェノキシ)-フェニル}プロパン、ビス(3,5-ジメチル-4-マレイミドフェニル)メタン、ビス(3-エチル-5-メチル-4-マレイミドフェニル)メタン、ビス(3,5-ジエチル-4-マレイミドフェニル)メタン、ポリテトラメチレンオキシド-ビス(4-マレイミドベンゾエート)、2,2-ビス[4-(4-マレイミドフェノキシ)フェニル]プロパン、下記式(VII)で表されるマレイミド化合物、下記式(IX)で表されるマレイミド化合物、これらマレイミド化合物のプレポリマー、及びマレイミド化合物とアミン化合物とのプレポリマーが挙げられる。これらは一種又は二種以上を適宜混合して使用することも可能である。
式(VII)中、
R11及びR12は、それぞれ独立して、ハロゲノ基、C1~C6アルキル基、水酸基、C1~C6アルコキシ基、ホルミル基、カルボキシル基、C1~C6アルコキシカルボニル基、C6~C10アリール基、アミノ基、C1~C6アルキル基置換アミノ基、シアノ基、またはニトロ基を示し、
a1及びa2は、それぞれ独立して、0~4の整数を示し、a1が2以上のときR11は互いに同じでも異なってもよく、a2が2以上のときR12は互いに同じでも異なってもよく、
m3及びm4は、それぞれ独立して、1~10の整数を示し、
R13及びR14は、それぞれ独立して、C1~C6アルキル基、またはC6~C10アリール基であり、
a3は、0~3の整数を示し、a3が2以上のときR13は互いに同じでも異なってもよく、
a4は、0~2の整数を示し、a4が2のときR14は互いに同じでも異なってもよく、
n1は、1~100の整数を示す。
R11及びR12における「C1~C6アルキル基」としては、は、直鎖であってもよいし、分岐鎖であってもよい。C1~C6アルキル基としては、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ペンチル基、n-ヘキシル基、I-プロピル基、I-ブチル基、s-ブチル基、t-ブチル基、I-ペンチル基、ネオペンチル基、2-メチルブチル基、2,2-ジメチルプロピル基、I-ヘキシル基などを挙げることができる。
R11及びR12における「C1~C6アルコキシ基」としては、メトキシ基、エトキシ基、n-プロポキシ基、I-プロポキシ基、n-ブトキシ基、s-ブトキシ基、I-ブトキシ基、t-ブトキシ基等を挙げることができる。
R11及びR12における「C1~C6アルコキシカルボニル基」としては、メトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、I-プロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基等を挙げることができる。
R11及びR12における「C6~C10アリール基」としては、フェニル基、ナフチル基等を挙げることができる。
R11及びR12における「C1~C6アルキル基置換アミノ基」は、モノ置換体、ジ置換体のいずれかであってよい。「C1~C6アルキル基置換アミノ基」としては、メチルアミノ基、ジメチルアミノ基、エチルアミノ基、ジエチルアミノ基、メチルエチルアミノ基等を挙げることができる。
式(VIII)中、n2は、1~100いずれかの整数を示す。
n2は、1~50であることが好ましく、1~20であることがより好ましく、1~5であることが更に好ましい。
式(IX)中、R15およびR16は、それぞれ独立して、水素原子、またはC1~C6アルキル基を示し、n3は、1~10の整数を示し、X4およびX5は、それぞれ独立して、C1~C6アルキル基を示し、S1およびS2は、それぞれ独立して、0~2のいずれかの整数を示し、S1が2のときX4は互いに同じでも異なってもよく、S2が2のときX5は互いに同じでも異なってもよい。
R15およびR16における「C1~C6アルキル基」としては、R11及びR12において例示したそれと同じものを挙げることができる。
R15およびR16は、水素原子またはメチル基であることが好ましく、水素原子であることがより好ましい。
n3は、1~7の整数であることが好ましく。1~3の整数であることがより好ましく、1であることが更に好ましい。
X4およびX5における「C1~C6アルキル基」としては、R11及びR12において例示したそれと同じものを挙げることができる。
X4およびX5は、メチル基またはエチル基であることが好ましい。
式(IX)で表される化合物は、4,4’-ジフェニルメタンビスマレイミド、またはビス(3-エチル-5-メチル-4-マレイミドフェニル)メタンであることが好ましい。
本発明に用いるポリフェニレンエーテル化合物は、下記式(X)で表される繰り返し単位を有するポリマーである限り特に限定されない。
式(X)中、R17~R20は、それぞれ独立に、水素原子、C1~C6アルキル基、C2~C6アルケニル基、C2~C6アルキニル基、C1~C6アルキルカルボニル基、又はC2~C6アルケニルカルボニル基を示す。
R17~R20における「C2~C6アルケニル基」としては、ビニル基、アリル基等を挙げることができる。
R17~R20における「C2~C6アルキニル基」としては、エチニル、2-プロピニル等を挙げることができる。
R17~R20における「C1~C6アルキルカルボニル基」としては、アセチル基等を挙げることができる。
R17~R20における「C2~C6アルケニルカルボニル基」としては、アクリロイル基、メタクリロイル基等を挙げることができる。
R17~R20は、水素原子、C1~C6アルキル基、またはC2~C6アルケニル基であることが好ましく、水素原子、メチル基、またはアリル基であることがより好ましく、水素原子、またはメチル基であることが更に好ましい。
式(VI)中、*は、結合位置を示し、pは、0~10の整数を示し、Z4は、アリーレン基を示し、R8~R10は、それぞれ独立に、水素原子、またはC1~C6のアルキル基を示す。
Z4におけるC6~C12アリーレン基としては、フェニレン基を挙げることができる。
R8~R10における、C1~C6アルキル基としては、R11及びR12において例示したそれと同じものを挙げることができる。
式(3)中、X6及びX7は、それぞれ独立して、式(VI)で表される基、アクリロイル基またはメタクリロイル基を示し、S3及びS4は、それぞれ独立して、0~20の整数を示す。X6及びX7における式(VI)で表される基は、前記した通りである。
式(4)中、X8及びX9は、それぞれ独立して、式(VI)で表される基、アクリロイル基またはメタクリロイル基を示し、S5及びS6は、それぞれ独立して、0~20の整数を示し、Y1は、C1~C6アルキレン基を示す。X8及びX9における式(VI)で表される基は、前記した通りである。Y1における「C1~C6アルキレン基」としては、メチレン基、エチレン基、メチルメチレン基、ジメチルメチレン基等を挙げることができる。
また、本発明で用いるポリフェニレンエーテル化合物の固有粘度は、0.03~0.12dl/g、0.04~0.11dl/g、0.06~0.095dl/gなどを挙げることができる。固有粘度は、25℃の塩化メチレン中で測定した固有粘度である。より具体的には、0.18g/45mlの塩化メチレン溶液(液温25℃)を、粘度計で測定した値である。
合成する場合は、WO2014/203511号などに記載された方法およびそれに準ずる方法により合成することができる。
本発明に用いられるポリブタジエンは、式(1)で表される1,2結合構造のみ、又は、式(1)で表される1,2結合構造と式(2)で表される1,4結合構造からなる。
ポリブタジエン中に含まれる式(1)で表される1,2結合構造と式(2)で表される1,4結合構造の割合は特に限定されないが、ポリブタジエンの全繰り返し単位中、式(I)で表される1,2結合構造のモル比は、80:20~100:0であるのが好ましい。
用いるポリブタジエンの分子量は特に限定されないが、重量平均分子量(Mw)が、500~10,000、500~8,000、500~6,000、500~5,000の範囲を選択することができる。なお、重量平均分子量(Mw)は、テトラヒドロフランを溶媒とするゲルパーミエーションクロマトグラフィー(GPC)にて測定したデータを標準ポリスチレンの分子量に基づいて換算した値である。
ポリブタジエンは、主鎖および末端が変性されたポリブタジエンであってもよいし、主鎖および末端が変性されていないポリブタジエンであってもよい。それらのうち、高い絶縁性を有する硬化物を得るという観点からは、主鎖および末端が変性されていないポリブタジエンを用いるのが好ましい。
ポリブタジエンとしては、市販品を用いることができる。市販品のポリブタジエンとしては、NISSO-PB B-1000(日本曹達(株)製)、NISSO-PB B-2000(日本曹達(株)製)、NISSO-PB B-3000(日本曹達(株)製)などを挙げることができる。これらのポリブタジエンは、1種単独でまたは2種以上を組み合わせて使用することができる。
本発明に用いられるスチレン-ブタジエン-スチレンブロック共重合体(SBS)中のスチレンブロックは、スチレンを重合したブロックであり、ブタジエンブロックはブタジエンを重合したブロックである。ブタジエンブロックは、式(1)で表される1,2結合構造のみ、又は、式(1)で表される1,2結合構造と、式(2)で表される1,4結合構造からなる。
本発明に用いられるスチレン-ブタジエン-スチレンブロック共重合体に含まれる、式(1)で表される1,2結合構造と、式(2)で表される1,4結合構造のモル比は、80:20~100:0である。
スチレン-ブタジエン-スチレンブロック共重合体中のスチレンブロックとブタジエンブロックの重量比は、特に限定されないが、10:90~80:20、10:90~70:30、10:90~60:40、20:80~80:20、30:70~80:20、40:60~80:20を挙げることができる。
スチレン-ブタジエン-スチレンブロック共重合体の重量平均分子量(Mw)は、特に限定されないが、2,000~100,000、2,000~80,000、2,000~60,000などを挙げることができる。スチレン-ブタジエン-スチレンブロック共重合体の分子量分布(Mw/Mn)は特に限定されないが、1.00~3.00、1.00~2.00などを挙げることができる。前記重量平均分子量(Mw)や分子量分布(Mw/Mn)は、ポリスチレンを標準物質として、ゲルパーミエーションクロマトグラフ(GPC)で測定したものである。その測定条件は、移動相THF(テトラヒドロフラン)、移動相流量1mL/分、カラム温度40℃、試料注入量40μL、試料濃度2重量%である。
用いるスチレン-ブタジエン-スチレンブロック共重合体の製造方法は特に限定されない。例えば、特開平6-192502号公報、特表2000-514122号公報、特開2007-302901号公報、WO2021/024679などに記載された方法およびそれに準ずる方法により製造することができる。
本発明の樹脂組成物は、分子中に式(V)で表される繰り返し単位を有する重合体を含有しうる。
式(V)中、Z3は、C6~C12アリーレン基を示し、R2~R7は、それぞれ独立に、水素原子、またはC1~C6のアルキル基を示す。
R2~R7における「C1~C6アルキル基」としては、R11及びR12において例示したそれと同じものを挙げることができる。
また、さらに、式(V)で表される繰り返し単位と式(5)で表される繰り返し単位以外の繰り返し単位を有していてもよい。
すなわち、(B-6)成分の分子中に式(V)で表される繰り返し単位を有する重合体は、以下の重合体を包含する。
I) 式(V)で表される繰り返し単位の1種または2種以上からなる重合体
II) 式(V)で表される繰り返し単位の1種または2種以上と、式(5)で表される繰り返し単位の1種または2種以上とからなる重合体
III) 式(V)で表される繰り返し単位の1種または2種以上と、式(5)で表される
繰り返し単位の1種または2種以上と、これら以外の繰り返し単位とからなる重合体
これらの重合体のうち、共重合体は、ランダム共重合体であっても、ブロック共重合体であってもよい。
式(5)中、R21~R23は、それぞれ独立して、水素原子、またはC1~C6アルキル基を示し、Ar1は、C1~C6アルキル基置換若しくは無置換のC6~C12アリール基を示す。
R21~R23における「C1~C6アルキル基」としては、R11及びR12において例示したそれと同じものを挙げることができる。
Ar1における「C6~C12アリール基」としては、フェニル基、ナフチル基、またはビフェニル基等を挙げることができる。
Ar1上の置換基である「C1~C6アルキル基」としては、R11及びR12において例示したそれと同じものを挙げることができる。
また、分子中に式(V)で表される繰り返し単位を有する重合体が、前記式(V)で表される繰り返し単位と式(5)で表される繰り返し単位とを分子中に有する重合体の場合、前記式(V)で表される繰り返し単位のモル含有率は、2~95モル%であることが好ましく、8~81モル%であることがより好ましく、前記式(5)で表される繰り返し単位のモル含有率は、5~98モル%であることが好ましく、19~92モル%であることがより好ましい。
(メタ)アクリレート樹脂としては、単官能(メタ)アクリレートモノマー又は(メタ)アクリレートオリゴマーなどを用いることができる。なかでも重合可能な不飽和基を2つ以上有する多官能(メタ)アクリレ-トなどを含んでいることが好ましい。
ビニル化合物類としては、スチレン等や、トリアリルイソシアヌレート(TAIC)等のトリアルケニルイソシアヌレート化合物、ジビニルベンゼン、ジビニルビフェニル、ジビニルナフタレン、両末端にビニル基を含有する変性ポリフェニレンエーテル系樹脂、全炭素-炭素二重結合を全量として、1,2体の合計量が50%以上であるポリブタジエン、全炭素-炭素二重結合を全量として、1,2体の合計量が50%以上であるポリブタジエンを有するスチレンーブタジエン共重合体等のように分子中にビニル基を2個以上有するビニル化合物(多官能ビニル化合物)、及び両末端にビニルベンジル基を含有する変性ポリフェニレンエーテル系樹脂、ポリジビニルベンゼン、ポリジビニルベンゼン樹脂、ジビニルベンゼンースチレン共重合体等のように分子中にビニルベンジル基を2個以上有するビニルベンジル化合物等が挙げられる。ビニル化合物類としては、上記した分子中に不飽和二重結合を2個以上有する化合物と、分子中に不飽和二重結合を1個有する化合物とを併用してもよい。分子中に不飽和二重結合を1個有する化合物としては、具体的には、分子中にビニル基を1個有する化合物(モノビニル化合物)等が挙げられる。
(B)成分である熱硬化性樹脂として、上記(B-2)~(B-8)から選択される少なくとも1種以上を用いる場合、本発明の樹脂組成物は、更に架橋剤を含むことができる。架橋剤は、(B)成分に含まれる不飽和炭素結合と反応し、3次元架橋を形成するものである。
トリメチロールプロパン等の(メタ)アクリレート化合物(メタクリレート化合物およびアクリレート化合物);
アセナフチレン骨格を有する化合物などが挙げられる。これらの架橋剤を用いると耐熱性を高めることができる。架橋剤は、1種のみを用いてもよいし、2種以上を用いてもよい。
3-ヒドロキシアセナフチレン、4-ヒドロキシアセナフチレン、5-ヒドロキシアセナフチレン、5,6-ジヒドロキシアセナフチレン等のヒドロキシアセナフチレン化合物;
3-メチルアセナフチレン、3-エチルアセナフチレン、3-プロピルアセナフチレン、4-メチルアセナフチレン、4-エチルアセナフチレン、4-プロピルアセナフチレン、5-メチルアセナフチレン、5-エチルアセナフチレン、5-プロピルアセナフチレン、3,8-ジメチルアセナフチレン、5,6-ジメチルアセナフチレン等のアルキルアセナフチレン化合物、3-メトキシアセナフチレン、3-エトキシアセナフチレン、3-ブトキシアセナフチレン、4-メトキシアセナフチレン、4-エトキシアセナフチレン、4-ブトキシアセナフチレン、5-メトキシアセナフチレン、5-エトキシアセナフチレン、5-ブトキシアセナフチレン等のアルコキシアセナフチレン化合物;
3-クロロアセナフチレン、3-ブロモアセナフチレン、4-クロロアセナフチレン、4-ブロモアセナフチレン、5-クロロアセナフチレン、5-ブロモアセナフチレン等のハロゲン化アセナフチレン化合物等が挙げられる。
(B)成分である熱硬化性樹脂として(B-2)~(B-8)から選択される少なくとも1種以上を用いる場合、本発明の樹脂組成物は、重合開始剤を含むことができる。
本発明の樹脂組成物に用いられる重合開始剤には、アゾ系の重合開始剤及び過酸化物系の重合開始剤等がある。
(シクロヘキサン-1-カルボニトリル)、2,2'-アゾビス{2-メチル-N-[1,1-ビス(ヒドロキシメチル)エチル]プロピオンアミド}、2、2'-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド]、2、2'-アゾビス[2-(ヒドロキシメチル)プロピオニトリル]、2,2'-アゾビス(2、4-ジメチルバレロニトリル)、2,2'-アゾビス(4-メトキシ-2、4-ジメチルバレロニトリル)、2,2'-アゾビスイソ酪酸ジメチル、2,2'-アゾビス[2-(2-イミダゾリン-2-イル)プロパン]、2,2'-アゾビス{2-メチル-N-[1、1-ビス(ヒドロキシメチル)-2-ヒドロキシエチル]プロピオンアミド}などを例示することができる。
(B)成分として(B-1)エポキシ樹脂を用いる場合、本発明の樹脂組成物中の(A)成分の含有量は特に制限されないが、(B)成分の量に対し、1~99重量%、1~50重量%、1~30重量%等を挙げることができる。
(B)成分として(B-2)~(B-8)から選択される少なくとも1種以上を用いる場合、本発明の樹脂組成物中の(A)成分の含有量はとくに制限されないが、(B)成分と架橋剤を合わせた量に対して、1~99重量%、10~70重量%、10~50重量%等を挙げることができる。
本発明の樹脂組成物中の(B)成分と架橋剤の含有比は特に制限されないが、重量比で、(B)成分:架橋剤=99:1~1:99、90:10~30:70、90:10~50:50等を挙げることができる。
また、本発明の樹脂組成物中の重合開始剤の含有量は、特に制限されないが、(B)成分と架橋剤を合わせた量に対して、0.1~10重量%となる量を挙げることができる。
本発明の樹脂組成物は、本発明の効果を損なわない範囲で、必要に応じて、その他の成分を含有しても良い。その他の成分としては、有機溶媒、熱可塑性樹脂、無機充填剤、有機充填剤、難燃剤、その他添加剤等を挙げることができる。
有機溶媒としては、アミド系、エーテル系、エステル系、脂肪族炭化水素系、芳香族炭化水素系、ケトン系、有機ハロゲン化合物系等が挙げられる。
アミド系の有機溶媒としては、N,N-ジメチルホルムアミド(DMF)、N,N-ジメチルアセトアミド;エーテル系の有機溶媒としてはジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジアミルエーテル、テトラヒドロフラン;エステル系の有機溶媒としてはエチルアセテート、プロピルアセテート、ブチルアセテート、アミルアセテート、ヘプチルアセテート、エチルブチレート、イソアミルイソバリレート、プロピレングリコールメチルエーテルアセタート;脂肪族系炭化水素系の有機溶媒としてはノルマルヘキサン、ノルマルヘプタン、シクロヘキサン;芳香族炭化水素系の有機溶媒としてはトルエン、キシレン;ケトン系の有機溶媒としてはメチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン;有機ハロゲン化物系の有機溶媒としてはトリクロロエタン、トリクロロエチレン;等が挙げられる。さらには、プロピレングリコールモノメチルエーテルやプロピレングリコールモノエチルエーテルなどの比較的非活性な有機溶媒も使用可能である。
熱可塑性樹脂としては、例えば、ポリアクリレート樹脂、ポリメタクリレート樹脂、ポリスチレン樹脂、ポリフェニレンエーテル樹脂、ポリエーテルイミド樹脂、ポリエーテルサルホン樹脂、ポリフェニレンサルファイド樹脂、ポリシクロペンタジエン樹脂、ポリシクロオレフィン樹脂、ポリシクロオレフィンコポリマー樹脂、ポリアリレート樹脂、ポリエーテル樹脂、フェノキシ樹脂、ポリビニルアセタール樹脂、ポリオレフィン樹脂、ポリブタジエン樹脂、ポリイミド樹脂、ポリアミドイミド樹脂、ポリエーテルイミド樹脂、ポリスルホン樹脂、ポリエーテルスルホン樹脂、ポリカーボネート樹脂、ポリエーテルエーテルケトン樹脂、ポリエステル樹脂、液晶ポリエステル樹脂、フッ素樹脂等や、既知の熱可塑性エラストマー、例えば、スチレン-エチレン-プロピレン共重合体、スチレン-エチレン-ブチレン共重合体、スチレン-ブタジエン共重合体、スチレン-イソプレン共重合体、水添スチレン-ブタジエン共重合体、水添スチレン-イソプレン共重合体、(メタ)アクリロニトリル-ブタジエン-(メタ)アクリル酸共重合体、(メタ)アクリロニトリル-ブタジエン-メチル(メタ)アクリレート共重合体、メチル(メタ)アクリレート-ブタジエン-スチレン共重合体(MBS)、並びに、(メタ)アクリロニトリル-ブタジエンゴム(NBR)、線状ポリウレタン、ポリブタジエン、ポリイソプレン、フッ素系ゴム、エチレンープロピレンージエンゴム等を挙げることができる。
無機充填剤の材料は特に限定されないが、例えば、シリカ、アルミナ、ガラス、コーディエライト、シリコン酸化物、硫酸バリウム、炭酸バリウム、タルク、クレー、雲母粉、酸化亜鉛、ハイドロタルサイト、ベーマイト、水酸化アルミニウム、水酸化マグネシウム、炭酸カルシウム、炭酸マグネシウム、酸化マグネシウム、窒化ホウ素、窒化アルミニウム、窒化マンガン、ホウ酸アルミニウム、炭酸ストロンチウム、チタン酸ストロンチウム、チタン酸カルシウム、チタン酸マグネシウム、チタン酸ビスマス、酸化チタン、酸化ジルコニウム、チタン酸バリウム、チタン酸ジルコン酸バリウム、ジルコン酸バリウム、ジルコン酸カルシウム、リン酸ジルコニウム、及びリン酸タングステン酸ジルコニウム等が挙げられる。これらの中でもシリカが特に好適である。またシリカとしては球形シリカが好ましい。無機充填剤は1種単独で用いてもよく、2種以上を組み合わせて用いてもよい。
有機充填剤としては、ゴム粒子、フッ素樹脂粒子(フッ素系ポリマー粒子)、ポリアミド微粒子、シリコーン粒子等が挙げられる。
フッ素樹脂粒子(フッ素系ポリマー粒子)としては、例えば、ポリテトラフルオロエチレン(PTFE)、パーフルオロアルコキシアルカン(PFA)、パーフルオロエチレンプロペンコポリマー(FEP)、エチレン・テトラフルオロエチレンコポリマー(ETFE)、テトラフルオロエチレン-パーフルオロジオキソールコポリマー(TFE/PDD)、ポリフッ化ビニリデン(PVDF)、ポリクロロトリフルオロエチレン(PCTFE)、エチレン-クロロトリフルオロエチレンコポリマー(ECTFE)、ポリフッ化ビニル(PVF)が挙げられる。これらの樹脂は1種を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
難燃剤は特に限定されないが公知の難燃剤を使用することができる。
具体的には、臭素系難燃剤等のハロゲン系難燃剤を使用する分野では、例えば、融点が300℃以上のエチレンジペンタブロモベンゼン、エチレンビステトラブロモイミド、デカブロモジフェニルオキサイド、及びテトラデカブロモジフェノキシベンゼンが好ましい。ハロゲン系難燃剤を使用することにより、高温時におけるハロゲンの脱離が抑制でき、耐熱性の低下を抑制できると考えられる。また、ハロゲンフリーが要求される分野では、リン酸エステル系難燃剤、ホスファゼン系難燃剤、及びホスフィン酸塩系難燃剤等のリン系の難燃剤が挙げられる。リン酸エステル系難燃剤の具体例としては、ジキシレニルホスフェートの縮合リン酸エステルが挙げられる。ホスファゼン系難燃剤の具体例としては、フェノキシホスファゼンが挙げられる。ホスフィン酸塩系難燃剤の具体例としては、例えば、ジアルキルホスフィン酸アルミニウム塩のホスフィン酸金属塩が挙げられる。例示した各難燃剤を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
その他添加剤としては、例えば、シリコーン系消泡剤及びアクリル酸エステル系消泡剤等の消泡剤、有機銅化合物、有機亜鉛化合物及び有機コバルト化合物等の有機金属化合物、レベリング剤、シランカップリング剤等の接着助剤、タッキファイヤー等の粘着付与剤、熱安定剤、帯電防止剤、BHT等の保存安定剤、酸化防止剤、光安定剤、紫外線吸収剤、染料や顔料、滑剤、湿潤分散剤、重金属不活性剤、イオントラップ剤、乳化剤、水分散安定剤、離型剤、ワックス、レオロジーコントロール剤、界面活性剤等が挙げられる。
本発明の樹脂組成物は、ソルダーレジスト、アンダ-フィル材、ダイボンディング材、半導体封止材、穴埋め樹脂、部品埋め込み樹脂、プリント配線板の絶縁材等、樹脂組成物が必要とされる用途の広範囲に使用できる。本発明の樹脂組成物は、好ましくは、プリント配線板の絶縁層用樹脂組成物である。プリント配線板とは、片面プリント基板、両面プリント基板、多層プリント基板、フレキシブルプリント基板、ビルドアップ基板用等が挙げられる。また、本発明の樹脂組成物の形態としては、特に限定されないが、接着フィルム、プリプレグ等のシート状積層材料、プリント配線板に適用することが出来る。本発明の樹脂組成物は、ワニス状態でプリント配線板に塗布して絶縁層を形成することもできるが、工業的には一般に、接着フィルム、プリプレグ等のシート状積層材料の形態として絶縁層形成に用いられる。
本発明の樹脂組成物を硬化させて得られる硬化物は、成型物、プリント配線板用絶縁体、金属箔付き積層物、注型物、接着剤、塗膜、フィルムとして使用できる。例えば、半導体封止材料の硬化物は注型物又は成型物であり、かかる用途の硬化物を得る方法としては、硬化性樹脂組成物を注型、或いはトランスファ-成形機、射出成形機などを用いて成形し、さらに80~230℃で0.5~10時間に加熱することにより硬化物を得ることができる。
本発明の樹脂組成物は、プリプレグを形成するための基材(繊維質基材)に含浸する目的、接着フィルムを形成するための支持フィルムに塗布をする目的、あるいはプリント配線板を形成する目的でワニス状に調製して、樹脂ワニスとすることができる。
この樹脂ワニスは、特に、プリント配線板用に適し、プリント配線板用ワニスとして使用できる。
各成分を、有機溶媒に投入して溶解させる。この際、必要に応じて、加熱してもよい。その後、必要に応じて、無機充填材等の有機溶媒に溶解しない成分を添加して、ボールミル、ビーズミル、プラネタリーミキサー、ロールミル等を用いて、分散させることにより、ワニス状の硬化性樹脂組成物が調製される。
本発明の樹脂組成物は、シート状積層材料に用いることができる。シート状積層材料としては、プリプレグ、接着フィルム等が挙げられる。
本発明のプリプレグは、本発明の樹脂組成物が基材に含侵されていることを特徴としている。
基材としては、ガラスクロス、アラミドクロス、ポリエステルクロス、ガラス不織布、アラミド不織布、ポリエステル不織布、パルプ紙、及びリンター紙等の繊維質基材が挙げられる。
本発明のプリプレグは、公知の方法で製造することができる。例えば、本発明の樹脂ワニスを基材に含侵させた後、乾燥する方法が挙げられる。
樹脂ワニスが含侵された基材を、所望の加熱条件、例えば、80~170℃で1~10分間加熱して溶媒を除去することにより半硬化状態(Bステージ)のプリプレグを得ることができる。
本発明の接着フィルムは、本発明の樹脂組成物を含有する樹脂組成物層を支持フィルム上に有することを特徴としている。本発明の接着フィルムは、公知の方法により製造することができる。例えば、本発明の樹脂ワニスを、ダイコーダーなどを用いて、支持フィルムに塗布し、さらに加熱、あるいは熱風吹きつけ等により有機溶剤を乾燥させて樹脂組成物層を形成させることにより製造することができる。
本発明のプリント配線板用絶縁体は、本発明のプリプレグ及び本発明の接着フィルムのいずれかの硬化物よりなるものである。本発明のプリント配線板用絶縁体の製造方法は特に限定されないが、例えば、シート状積層材料を一枚または複数枚重ね、これを加熱加圧成形する方法が挙げられる。本発明の本発明のプリント配線板用絶縁体は、片面プリント基板、両面プリント基板、多層プリント基板、フレキシブルプリント基板、ビルドアップ基板用の絶縁層として好適である。
本発明の金属箔付き積層物は、本発明のプリント配線板用絶縁体の層と金属箔の層とを備えるものである。ここで用いられる金属箔としては、例えば銅箔、アルミニウム箔等が挙げられる。その厚みは特に限定されないが、3~200μm、より好ましくは3~105μmの範囲である。
以下に実施例を示すが、本願発明の技術的範囲は実施例に限定されない。
実施例において得られたポリマーの重量平均分子量の測定は、以下の装置及び条件で行った。
[装置]
サンプル注入装置:Waters 2695 アライアンス
分離カラム:ShodexKF-G、805L、804L、804L
検出器:Waters 2414 示差屈折(RI)検出器
2998 フォトダイオードアレイ(PDA)検出器
カラムオーブン:Waters社製カラムオーブン
[条件]
カラムオーブン温度:40℃
RI検出器温度:40℃
移動相:テトラヒドロフラン
流量:1.0mL/mIn
標準注入量:200μL
PDA検出器抽出波:254.0nm
定量計算:標準ポリメタクリル酸メチル換算
ポリアクリルアミド10mgをサンプルとして用いて、DSC(示差走査熱量測定)装置(TAインスツルメント社製Q2000)を用いて昇温速度10℃/分の条件で昇温し、昇温曲線中のガラス転移に由来する2つの折曲点温度の中間値をガラス転移温度とした。
ポリアクリルアミドの粉体を用いて共振法にて以下の条件で測定した。
装置:株式会社エーイーティー社製、円筒型空洞共振器
周波数:1GHz
測定温度:23℃
ポリアクリルアミド50重量部に有機溶媒50重量部を加えて、室温で2時間撹拌した。静置1日後の樹脂溶液の状態を下の基準で評価した。なお、有機溶媒として、MEK、トルエン、シクロヘキサノンを用いた。
〇:樹脂溶液は流動性を有しており、透明であった。
△:樹脂溶液は流動性を有してはいたが、白濁していた。
×:樹脂溶液が流動性を有しておらず、樹脂が全く溶解していなかった。
N,N-ビス(4-(tert-ブチル)フェニル)アクリルアミドの合成
窒素置換した1Lの四ツ口フラスコに、ビス(4-tert―ブチルフェニル)アミン(100g,0.355mol)、N,N-ジメチルアニリン(64.59g,0.533mol),及び超脱水トルエン400mLを仕込み、均一に溶解するまで撹拌した。次に、反応溶液を氷/エタノールバスで0℃以下に冷却し、アクリル酸クロライド(38.59g,0.426mol)をゆっくり滴下し、30分間撹拌した。その後、反応液を室温まで昇温し、24時間反応を行った。反応終了後、1N塩酸水溶液、飽和重曹水、食塩水で水洗した。有機層を硫酸マグネシウムで脱水し、その後濾液をエバポレーターで留去した。得られた粗生成物をヘキサンで再結晶精製することで、N,N-ビス(4-(tert-ブチル)フェニル)アクリルアミド(92.90g,収率79%)を得た。
ポリアクリルアミドA;ポリ[N,N-ビス(4-(tert-ブチル)フェニル)アクリルアミド]の作製
300mL四つ口フラスコにN,N-ビス(4-(tert-ブチル)フェニル)アクリルアミド50g、AIBN0.15gを仕込み、トルエン75gに溶解させた。減圧操作を加えて脱気を行い、窒素雰囲気化で65℃、24時間加熱撹拌した。その後、AIBN 0.10gを加え、80℃で2時間撹拌した。加熱撹拌を停止するとともに反応液をサンプリングし、ゲルパーミエーションクロマトグラフィー測定を行った。反応液をメタノール1L中に滴下することで粉体化を行った。得られた析出物をろ別し、真空乾燥機にて60℃、減圧による乾燥を行った。
収量46.2g、Mw=58,000、Mw/Mn=2.40
N,N-ビス(4-(n-ブチル)フェニル)アクリルアミドの合成
窒素置換した300mLの四ツ口フラスコに、ビス(4-n-ブチルフェニル)アミン(25.4g,0.090mol)、N,N-ジメチルアニリン(21.09g,0.174mol),及び超脱水トルエン100mLを仕込み、均一に溶解するまで撹拌した。次に、反応溶液を氷/エタノールバスで0℃以下に冷却し、アクリル酸クロライド(9.46g,0.105mol)をゆっくり滴下し、30分間撹拌した。その後、反応液を室温まで昇温し、24時間反応を行った。反応終了後、1N塩酸水溶液、飽和重曹水、蒸留水で水洗した。有機層を硫酸マグネシウムで脱水し、その後濾液をエバポレーターで留去した。得られた粗生成物をヘキサン/酢酸エチル=4:1,v/vを溶媒としたシリカゲルカラムクロマトグラフィーで分離精製することで、N,N-ビス(4-(n-ブチル)フェニル)アクリルアミド(20.80g,収率69%)を得た。
ポリアクリルアミドB:ポリ[N,N-ビス(4-(n-ブチル)フェニル)アクリルアミド]の作製
100mL二つ口フラスコにN,N-ビス(4-(n-ブチル)フェニル)アクリルアミド 20g、AIBN0.06gを仕込み、トルエン22.5gに溶解させた。減圧操作を加えて脱気を行い、窒素雰囲気化で60℃、24時間加熱撹拌した。その後、AIBN0.10gを加え、60℃で24時間撹拌した。加熱撹拌を停止するとともに反応液をサンプリングし、ゲルパーミエーションクロマトグラフィー測定を行った。反応液をメタノール1L中に滴下することで粉体化を行った。得られた析出物をろ別し、真空乾燥機にて60℃、減圧による乾燥を行った。収量18.1g、Mw=76,000、Mw/Mn=2.89
各試薬を表2の組成(重量部)で、固形分濃度が50重量%となるように、トルエンに添加し、混合させた。その後、得られた液体からトルエンをエバポレーターで除去することで粉末状の樹脂組成物を得た。樹脂組成物を200℃で90分間、熱プレスすることで、硬化させた。得られた硬化物の物性を下記項目について測定し、結果を表2に示す。
<ガラス転移温度(Tg)>
DSC(示差走査熱量測定)装置(TAインスツルメント社製Q2000)を用いて昇温速度10℃/分の条件で昇温し、昇温曲線中のガラス転移に由来する2つの折曲点温度の中間値をガラス転移温度とした。
<誘電率試験(Dk)・誘電正接試験(Df)>
株式会社エーイーティー社製の円筒型空洞共振器(TEモード共振器)を用いて10GHzで測定を行った。
各試薬を表3の組成(重量部)で、固形分濃度が50重量%となるように、トルエンに添加し、混合させた。その後、得られた液体からトルエンをエバポレーターで除去することで粉末状の樹脂組成物を得た。樹脂組成物を200℃で120分間、熱プレスすることで、硬化させた。得られた硬化物の物性を下記項目について測定し、結果を表3に示す。
<ガラス転移温度(Tg)>
DSC(示差走査熱量測定)装置(TAインスツルメント社製Q2000)を用いて昇温速度10℃/分の条件で昇温し、昇温曲線中のガラス転移に由来する2つの折曲点温度の中間値をガラス転移温度とした。
<誘電率試験(Dk)・誘電正接試験(Df)>
株式会社エーイーティー社製の円筒型空洞共振器(TEモード共振器)を用いて10GHzで測定を行った。
Claims (20)
- Yが、アクリロイル基またはメタクリロイル基である、請求項1に記載のポリマー。
- 請求項1に記載のポリマーを含有する樹脂組成物。
- 更に、請求項1に記載のポリマー以外の樹脂を含有する、請求項3に記載の樹脂組成物。
- 請求項1に記載のポリマー以外の樹脂が熱硬化性樹脂である、請求項4に記載の樹脂組成物。
- 熱硬化性樹脂がエポキシ樹脂である、請求項5に記載の樹脂組成物。
- 更に、硬化剤として活性エステル系化合物を含有する、請求項6に記載の樹脂組成物。
- 請求項3に記載の樹脂組成物の硬化物を用いた、成形体。
- プリント配線板の絶縁層用樹脂組成物である、請求項3~9のいずれかに記載の樹脂組成物。
- 請求項3~9のいずれかに記載の樹脂組成物を含有する樹脂ワニス。
- 請求項3~9のいずれかに記載の樹脂組成物が基材に含侵されたプリプレグ。
- 請求項3~9のいずれかに記載の樹脂組成物を含有する樹脂組成物層を支持フィルム上に有することを特徴とする、接着フィルム。
- 請求項13に記載のプリプレグの硬化物よりなるプリント配線板用絶縁体。
- 請求項14に記載の接着フィルムの硬化物よりなるプリント配線板用絶縁体。
- 請求項15に記載のプリント配線板用絶縁体からなる層と金属箔からなる層とを備える金属箔付き積層物。
- 請求項16に記載のプリント配線板用絶縁体からなる層と金属箔からなる層とを備える金属箔付き積層物。
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WO2021024679A1 (ja) | 2019-08-06 | 2021-02-11 | 日本曹達株式会社 | ポリフェニレンエーテル樹脂組成物、プリプレグ、及び金属張積層板 |
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JP2022090373A (ja) | 2020-12-07 | 2022-06-17 | パイオニア株式会社 | 情報処理装置、制御方法、プログラム及び記憶媒体 |
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- 2022-07-08 KR KR1020247000609A patent/KR20240034183A/ko unknown
- 2022-07-08 EP EP22842057.6A patent/EP4372015A1/en active Pending
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KR20240034183A (ko) | 2024-03-13 |
EP4372015A1 (en) | 2024-05-22 |
TWI822177B (zh) | 2023-11-11 |
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