JP7444543B2 - エポキシ系硬化性組成物ならびに硬化物およびその製造方法 - Google Patents
エポキシ系硬化性組成物ならびに硬化物およびその製造方法 Download PDFInfo
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- JP7444543B2 JP7444543B2 JP2019059104A JP2019059104A JP7444543B2 JP 7444543 B2 JP7444543 B2 JP 7444543B2 JP 2019059104 A JP2019059104 A JP 2019059104A JP 2019059104 A JP2019059104 A JP 2019059104A JP 7444543 B2 JP7444543 B2 JP 7444543B2
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- boron nitride
- curable composition
- nitride particles
- epoxy
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- 239000004593 Epoxy Substances 0.000 title claims description 58
- 239000000203 mixture Substances 0.000 title claims description 40
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002245 particle Substances 0.000 claims description 72
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 57
- 239000003795 chemical substances by application Substances 0.000 claims description 57
- 229910052582 BN Inorganic materials 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 32
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 10
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 239000010680 novolac-type phenolic resin Substances 0.000 claims 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 45
- -1 polycyclic arene Chemical group 0.000 description 28
- 239000003822 epoxy resin Substances 0.000 description 21
- 229920000647 polyepoxide Polymers 0.000 description 21
- 239000005011 phenolic resin Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 229920001568 phenolic resin Polymers 0.000 description 14
- 238000006467 substitution reaction Methods 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000000463 material Substances 0.000 description 11
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 229920001187 thermosetting polymer Polymers 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
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- 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 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- XTIUBELQKDSHEO-UHFFFAOYSA-N 2-[[2-[9-[2-(oxiran-2-ylmethoxy)phenyl]fluoren-9-yl]phenoxy]methyl]oxirane Chemical class C1OC1COC1=CC=CC=C1C1(C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1OCC1CO1 XTIUBELQKDSHEO-UHFFFAOYSA-N 0.000 description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 description 4
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- 238000004898 kneading Methods 0.000 description 4
- 150000003018 phosphorus compounds Chemical class 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- LCSAOPVSVLGDLE-UHFFFAOYSA-N 2-[[4-[9-[4-(oxiran-2-ylmethoxy)phenyl]fluoren-9-yl]phenoxy]methyl]oxirane Chemical compound C1OC1COC(C=C1)=CC=C1C1(C2=CC=CC=C2C2=CC=CC=C21)C(C=C1)=CC=C1OCC1CO1 LCSAOPVSVLGDLE-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical group C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
- IHRQAMGCFUCIAH-UHFFFAOYSA-N 2-[[1-[9-[2-(oxiran-2-ylmethoxy)naphthalen-1-yl]fluoren-9-yl]naphthalen-2-yl]oxymethyl]oxirane Chemical class C1OC1COC1=CC=C2C=CC=CC2=C1C1(C2=CC=CC=C2C2=CC=CC=C21)C(C1=CC=CC=C1C=C1)=C1OCC1CO1 IHRQAMGCFUCIAH-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 150000004946 bicyclic arenes Chemical group 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 150000004948 tricyclic arenes Chemical group 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
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- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
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- 239000002841 Lewis acid Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 239000011231 conductive filler Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- MTWCVKTUVWXLFS-UHFFFAOYSA-N dipropylphosphane Chemical compound CCCPCCC MTWCVKTUVWXLFS-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- BXDCELKJGGVUHD-UHFFFAOYSA-N ethyl(methyl)phosphane Chemical compound CCPC BXDCELKJGGVUHD-UHFFFAOYSA-N 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000004947 monocyclic arenes Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 101150034433 terC gene Proteins 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 235000015149 toffees Nutrition 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 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
- 239000013638 trimer Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
エポキシ成分(A)は、9,9-ビスアリールフルオレン骨格を有するフルオレン含有エポキシ成分であってもよく、9,9-ビスアリールフルオレン骨格を有さないフルオレン非含有エポキシ成分であってもよいが、熱伝導性や耐熱性などの点から、フルオレン含有エポキシ成分を含むのが好ましい。
硬化剤(B)は、9,9-ビスアリールフルオレン骨格を有するフルオレン含有硬化剤であってもよく、9,9-ビスアリールフルオレン骨格を有さないフルオレン非含有硬化剤であってもよいが、エポキシ成分(A)が9,9-ビスアリールフルオレン骨格を有する場合、取り扱い性などの点から、フルオレン非含有硬化剤を含むのが好ましい。
窒化ホウ素粒子(C)を構成する窒化ホウ素は、六方晶窒化ホウ素、立方晶窒化ホウ素のいずれであってもよいが、生産性などの点から、六方晶窒化ホウ素が好ましい。
本発明の硬化性組成物は、前記エポキシ成分(A)、前記硬化剤(B)および前記窒化ホウ素粒子(C)に加えて、硬化促進剤をさらに含んでいてもよい。
本発明の硬化性組成物は、反応性希釈剤や溶媒をさらに含んでいてもよい。反応性希釈剤や溶媒の割合は、前記エポキシ成分(A)100質量部に対して500質量部以下であってもよく、例えば400質量部以下、好ましくは300質量部以下である。
本発明の硬化性組成物は、前記成分をホモジナイザー、ミキサーまたは混合機、混練機(ニーダーやロール、押出機など)、らいかい機(擂潰機)などを使用して、硬化反応(またはゲル化)が生じない温度、時間で混合または混練することにより調製してもよい。これらのうち、ロールを用いた溶融混練が好ましい。
本発明の硬化物は、硬化性組成物を加熱して硬化させることにより製造してもよい。具体的な製造方法としては、前記硬化性組成物を、基材へ塗布して硬化させる方法、所定部に注入または封止して硬化させる方法、注型して硬化させる方法、繊維基材などの基材に含浸してプリプレグを調製し、このプリプレグを、重ね合わせや巻回などの方法で積層して所定形状に成形加工して硬化させる方法などが挙げられる。
BPFG:9,9-ビス(4-グリシジルオキシフェニル)フルオレン
硬化剤:フェノールノボラック樹脂、東都化成(株)製「PSM-4261」
硬化促進剤:トリフェニルホスフィン、関東化学(株)製「トリフェニルホスフィン」
鱗片状窒化ホウ素(BN)粒子a:デンカ(株)製「MGP」、中心粒径15.31μm
鱗片状窒化ホウ素粒子b:デンカ(株)製「XGP」、中心粒径29.52μm
顆粒状窒化ホウ素粒子:昭和電工(株)製「UHP-G1H」。
原料の窒化ホウ素粒子の中心粒径をレーザー回折/散乱式粒子径分布測定装置((株)堀場製作所製LA―950V2)を用いて測定した。
実施例および比較例で得られた硬化性組成物を、直径φ50mm×厚み4~5mmの円盤状試験片に成形し、ASTM E1530(円板熱流計法)に準拠し、熱分析装置(ティー・エイ・インスツルメント社製「DTC-300型」)を用いて、温度23℃の条件で厚み方向の熱伝導率を測定した。
表1に示す組成比で、各成分を6インチミキシングロール((株)ダイハン製「DY6-15」)を用いて、110℃で5分間混練して調製した。
Claims (8)
- エポキシ成分(A)、硬化剤(B)、窒化ホウ素粒子(C)およびリン系硬化促進剤を含む硬化性組成物であって、
前記エポキシ成分(A)が、下記式(1A)で表される化合物またはその多量体を含み、かつ
前記化合物またはその多量体の割合が、前記エポキシ成分(A)中70質量%以上であるとともに、
前記硬化剤(B)が、ノボラック型フェノール樹脂であり、かつ
前記硬化剤(B)の割合が前記エポキシ成分(A)100質量部に対して10~80質量部である硬化性組成物。
- 前記窒化ホウ素粒子(C)の中心粒径が20μm以上である請求項1記載の硬化性組成物。
- 前記窒化ホウ素粒子(C)の形状が板状である請求項1または2記載の硬化性組成物。
- 前記エポキシ成分(A)の割合が、前記窒化ホウ素粒子(C)100質量部に対して1~50質量部である請求項1~3のいずれか1項に記載の硬化性組成物。
- 前記窒化ホウ素粒子(C)の割合が組成物中50質量%以上である請求項1~4のいずれか1項に記載の硬化性組成物。
- 請求項1~5のいずれか1項に記載の硬化性組成物が硬化した硬化物。
- 前記窒化ホウ素粒子(C)の体積割合が50体積%以上である請求項6記載の硬化物。
- 請求項1~5のいずれか1項に記載の硬化性組成物を加熱して硬化させ、請求項6または7記載の硬化物を製造する方法。
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JP2010132825A (ja) | 2008-12-08 | 2010-06-17 | Nippon Kayaku Co Ltd | エポキシ樹脂組成物、プリプレグおよびそれらの硬化物 |
JP2012039066A (ja) | 2010-01-29 | 2012-02-23 | Nitto Denko Corp | 熱伝導性シート |
WO2013118848A1 (ja) | 2012-02-08 | 2013-08-15 | 日東電工株式会社 | 熱伝導性シートの製造方法 |
JP2013177564A (ja) | 2012-02-08 | 2013-09-09 | Nitto Denko Corp | 熱伝導性シート、熱伝導性シート形成用粒子集合物粉体、および、これらの製造方法 |
WO2018147053A1 (ja) | 2017-02-07 | 2018-08-16 | 三菱瓦斯化学株式会社 | 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 |
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JP2010132825A (ja) | 2008-12-08 | 2010-06-17 | Nippon Kayaku Co Ltd | エポキシ樹脂組成物、プリプレグおよびそれらの硬化物 |
JP2012039066A (ja) | 2010-01-29 | 2012-02-23 | Nitto Denko Corp | 熱伝導性シート |
WO2013118848A1 (ja) | 2012-02-08 | 2013-08-15 | 日東電工株式会社 | 熱伝導性シートの製造方法 |
JP2013177564A (ja) | 2012-02-08 | 2013-09-09 | Nitto Denko Corp | 熱伝導性シート、熱伝導性シート形成用粒子集合物粉体、および、これらの製造方法 |
WO2018147053A1 (ja) | 2017-02-07 | 2018-08-16 | 三菱瓦斯化学株式会社 | 樹脂組成物、プリプレグ、金属箔張積層板、樹脂シート及びプリント配線板 |
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