JP2021502370A - リン酸化無水物含有エポキシ樹脂 - Google Patents
リン酸化無水物含有エポキシ樹脂 Download PDFInfo
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- JP2021502370A JP2021502370A JP2020525898A JP2020525898A JP2021502370A JP 2021502370 A JP2021502370 A JP 2021502370A JP 2020525898 A JP2020525898 A JP 2020525898A JP 2020525898 A JP2020525898 A JP 2020525898A JP 2021502370 A JP2021502370 A JP 2021502370A
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- Prior art keywords
- epoxy resin
- compound according
- curable composition
- compound
- phenyl
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- 229920000647 polyepoxide Polymers 0.000 title claims description 83
- 239000003822 epoxy resin Substances 0.000 title claims description 78
- 150000008064 anhydrides Chemical class 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 13
- -1 methoxy, cyclopentyl Chemical group 0.000 claims description 57
- 229910052698 phosphorus Inorganic materials 0.000 claims description 49
- 239000011574 phosphorus Substances 0.000 claims description 46
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 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 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000003367 polycyclic group Chemical group 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 229920003986 novolac Polymers 0.000 claims description 16
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 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 claims description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229920005862 polyol Polymers 0.000 claims description 9
- 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 claims description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 235000013824 polyphenols Nutrition 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 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 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
- 229930003836 cresol Natural products 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 4
- 239000004844 aliphatic epoxy resin Substances 0.000 claims description 4
- 239000004643 cyanate ester Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 3
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 150000004684 trihydrates Chemical class 0.000 claims description 3
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical class C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 claims description 2
- ILSRXKFYTXYKJS-UHFFFAOYSA-N 2,4-bis(ethenyl)-3,6-dioxatetracyclo[6.4.0.02,4.05,7]dodeca-1(12),8,10-triene Chemical class C=CC12OC1(C=C)C1=CC=CC=C1C1C2O1 ILSRXKFYTXYKJS-UHFFFAOYSA-N 0.000 claims description 2
- TZLVUWBGUNVFES-UHFFFAOYSA-N 2-ethyl-5-methylpyrazol-3-amine Chemical compound CCN1N=C(C)C=C1N TZLVUWBGUNVFES-UHFFFAOYSA-N 0.000 claims description 2
- GRWFFFOEIHGUBG-UHFFFAOYSA-N 3,4-Epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclo-hexanecarboxylate Chemical compound C1C2OC2CC(C)C1C(=O)OCC1CC2OC2CC1C GRWFFFOEIHGUBG-UHFFFAOYSA-N 0.000 claims description 2
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 claims description 2
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 claims description 2
- GLPDXGJXUWGMQJ-UHFFFAOYSA-N 4-ethenyl-7-(4-ethenylphenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical class C(=C)C1=CC=C(C=C1)C12C(C3C(C=C1)(C=C)O3)O2 GLPDXGJXUWGMQJ-UHFFFAOYSA-N 0.000 claims description 2
- BMIOTMCWMGQPAA-UHFFFAOYSA-N 5-methyl-3-[(5-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl]-7-oxabicyclo[4.1.0]heptane-3-carboxylic acid Chemical compound C1C2OC2C(C)CC1(C(O)=O)CC1CC(C)C2OC2C1 BMIOTMCWMGQPAA-UHFFFAOYSA-N 0.000 claims description 2
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 claims description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 2
- AJDPRSJBHBDFOZ-UHFFFAOYSA-N C1CC2OC2(C)CC1(C(O)=O)CC1CC(C)(O2)C2CC1 Chemical compound C1CC2OC2(C)CC1(C(O)=O)CC1CC(C)(O2)C2CC1 AJDPRSJBHBDFOZ-UHFFFAOYSA-N 0.000 claims description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000004020 conductor Substances 0.000 claims description 2
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 239000005350 fused silica glass Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 2
- HYYPKCMPDGCDHE-UHFFFAOYSA-N 4-(7-oxabicyclo[4.1.0]heptan-4-ylmethyl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1CC1CC2OC2CC1 HYYPKCMPDGCDHE-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- WPBVMCKCLRUETC-UHFFFAOYSA-N CCC1(C(O1)CC(C)(C)C(=O)O)C23CCCCC2O3 Chemical compound CCC1(C(O1)CC(C)(C)C(=O)O)C23CCCCC2O3 WPBVMCKCLRUETC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003014 reinforcing effect Effects 0.000 claims 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 7
- 239000004848 polyfunctional curative Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 6
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012779 reinforcing material Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 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 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
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- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- 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
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Abstract
Description
R1及びR2は独立して、アルキル、アルコキシ、シクロアルキル、−O−アルキル−シクロアルキル、−O−シクロアルキル、アリール、アリールオキシであり、又はR1とR2とが一緒になって多環式部分を形成し、各アリール又は多環式部分は、アルキル、アルコキシ、アリール、アリールオキシ、アリールアルキル、アルケニル、及びアルキニルから独立して選択される1つ又はそれ以上の基で任意に置換され、
R3は独立して、アルキル、シクロアルキル、又はアリールであり、各アリールは、アルキル、アルコキシ、アリール、アリールオキシ、アルケニル、及びアルキニルから独立して選択される1つ又はそれ以上の基で任意に置換され、
lは0、1、2、3、4、5、又は6であり、
式I又はIIの化合物を調製する方法、少なくとも1つのエポキシ樹脂及び式I又はIIの化合物を含む硬化性組成物、並びに硬化性組成物を硬化させることにより調製された硬化生成物も開示される。式I及びIIの化合物は、難燃剤、硬化剤又は両方として作用する。
lは0、1、2、又は3であり、mは0、1、2、3、又は4であり、nは0、1、2、3又は4であり、m及びnの少なくとも1つが0でない場合、各R4及びR5は独立して、アルキル、アルコキシ、アリール、アリールオキシ、アリールアルキル、アルケニル、及びアルキニルからなる群から選択される。1つの実施形態では、各R4及びR5は、C1−C6アルキル、C1−C6アルコキシ、フェニル、ナフチル、フェニルオキシ、ベンジル、フェネチル、C2−C6アルケニル、及びC2−C6アルキニルから独立して選択される。一実施形態では、R4及びR5は同じである。代替的に、それらは異なる場合がある。
a)少なくとも1つのエポキシ樹脂、及び
b)式I、II、III又はIVのリン−オレフィン付加物の少なくとも1つ
を含む硬化性組成物である。
Sanko Co.,Ltd.から入手可能なDOPO(9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキシド)
Sanko Co.,Ltd.から入手可能なBz−HCA(8−ベンジル−9,10−ジヒドロ−9−オキサ−10−ホスファフェナントレン−10−オキシド)
Sinopharm Chemical Co.から入手可能なメチルナディック酸無水物(MNA)
Sinopharm Chemical Co.から入手可能なメチルテトラヒドロ無水フタル酸(MTHPA)
Sinopharm Chemical Co.から入手可能なジ−tert−ブチルペルオキシド
Sinopharm Chemical Co.から入手可能な2−エチル−4−メチルイミダゾール(触媒)
Blue Cube Operation LLC.から入手可能なD.E.N.(商標)438(ノボラックエポキシ樹脂)
DIC.から入手可能なEPICLON HP−7200H(ノボラックエポキシ樹脂)
Sinopharm Chemical Co.から入手可能なベンゾオキサジン
Cray Valley.から入手可能なSMA2000(スチレン無水マレイン酸コポリマー)
Blue Cube Operation LLC.から入手可能なXZ−92741
Kolon Industries,Inc.から入手可能なKPH−F2003(フェノールノボラック)
ワニスを2116ガラスクロスに含浸させた。樹脂を含むガラスクロスをトリータで焼成し、プリプレグを部分硬化させた。6枚のプリプレグを共に重ね、表面を35μmの標準銅箔のシートで覆った。次いで、スタックをホットプレスにて200℃で90分間ラミネートした。
Tgは、IPC−TM650−2.4.25に従ってTA Q2000(TA Instruments製)の示差走査熱量測定(DSC)で測定した。通常、サーマルスキャンは40℃〜210℃の範囲であり、加熱速度20℃/分を使用した。2回の加熱サイクルが実行され、2番目のサイクルの曲線が「ハーフハイト」法によるTgの決定に使用された。
Tdは、窒素中の重量損失が5%の温度として定義される。IPC−TM650−2.4.24.6に従ってTA Q50(TA Instruments製)で測定された。昇温速度は10℃/分であった。
T288はIPC−TM−2.4.24.1に従ってTA Q400(TA Instruments製)で測定された。層間剥離までの時間は、温度が288℃に達してから急激な寸法変化が発生するまでの経過時間として決定された。
ラミネート試料の誘電率及び散逸率(dissipation factor)は、ASTM D−150に準拠して、25℃、1GHzでAgilent16453A試験装置を装備したAgilent E4991A RFインピーダンス/材料アナライザによって決定された。
銅剥離強度は、試験全体を通して所望の90°剥離角度を維持できる可変角度剥離装置を備えたIMASS SP−2000スリップ/ピールテスターを使用して測定した。銅エッチングのために、2インチ×4インチの銅クラッドラミネートが切断された。0.25インチのグラファイトテープの2つのストリップを、サンプルに沿ってラミネートの両面に縦方向に、少なくとも0.5インチの間隔で配置した。次に、ラミネート片をKeyProベンチトップエッチャーに配置した。エッチャーからサンプルを取り出して適切に乾燥させたら、グラファイトテープを除去して銅のストリップを露出させた。かみそりの刃を使用して、各銅ストリップを引き上げた。次に、ラミネートをIMASSテスターにロードした。銅ストリップをクランプし、銅剥離試験を2.8インチ/分の引張速度で90°の角度で実施した。
銅アンクラッドラミネートを2インチ×3インチのサイズで4片に切断した。サンプルを正確に計量し、オートクレーブ(Thermo Electron Corp.8000−DSE)に入れた。サンプルは、121℃の水蒸気下で1時間処理した。表面水を拭き取り、サンプルを再度正確に計量して平均吸水率を計算した。
5つの試料(13cm×12mm)のそれぞれを、標準のUL94試験チャンバ(Atlas UL94チャンバVW−1)で10秒間2回点火した。点火源を離してから自己消火するまでの時間を燃焼時間として記録した。UL94V−0の評価付けには、各点火で10秒未満の燃焼時間、及び10回の点火で50秒未満の合計燃焼時間が必要である。
以下の例は、本開示の範囲を例示するために与えられ、限定するものではない。
DOPO(172.50g)を140℃で溶融させた。MNA(143.55g)及びジ−tert−ブチルペルオキシド(3.74g)の混合物を、45分かけて徐々に、溶融したDOPOに添加した。混合物を140〜160℃で8時間加熱した。最終生成物は、室温で淡褐色の固体であった。
DOPO(323.15g)を140℃で溶融した。MTHPA(250.68g)とジ−tert−ブチルペルオキシド(11.08g)との混合物を、70分かけて徐々に、溶融したDOPOに添加した。混合物を140〜160℃で7時間加熱した。最終生成物は、室温で淡褐色の固体であった。
Bz−HCA(30.52g)及びMTHPA(16.70g)を160℃で混合した。ジ−tert−ブチルペルオキシド(0.78g)を反応混合物に滴下した。混合物を160℃で7時間加熱した。最終生成物は、室温で淡褐色の固体であった。
実施例4〜6は、実施例1及び2の化合物をエポキシ樹脂と混合して硬化させた場合に得られた結果を記載する。
配合物は高いTg(>180℃)を示し、これは新しいリン酸化無水物がエポキシを硬化させるのに効果的な硬化剤であることを示した。
下の表には、配合作業及びラミネートの評価を示した。本発明の実施例7〜9はすべて、V−0 UL94等級を達成し、リン酸化無水物は、比較例のXZ−92741と同様に有効な難燃剤として作用することができることを示した。実施例7は1GHzで0.0074Dfを達成し、比較例よりも低く、これは、リン酸化無水物が、エポキシで硬化する場合に広く使用されているXZ−92741よりも有利にDfが低いことを示している。配合物に使用された無水物が多すぎるため、吸水率は高かった。ベンゾオキサジン又はSMAで配合をさらに変更すると、結果として得られた実施例8及び9のラミネートは、比較例と比較して、全体的にバランスの取れた性能、例えば高いTg、優れた耐熱性、優れた銅剥離強度、適度な吸水率、比較的低いDfを示した。
Claims (50)
- 式I又はIIの化合物であって、
R1及びR2は、独立して、アルキル、アルコキシ、シクロアルキル、−O−アルキル−シクロアルキル、−O−シクロアルキル、アリール、アリールオキシであり、又はR1とR2とは一緒になって多環式部分を形成し、各アリール又は多環式部分は、アルキル、アルコキシ、アリール、アリールオキシ、アリールアルキル、アルケニル、及びアルキニルから独立して選択される1つ又はそれ以上の基で任意に置換され、
R3は、独立して、水素、アルキル、シクロアルキル、又はアリールであり、各アリールは、アルキル、アルコキシ、アリール、アリールオキシ、アルケニル、及びアルキニルから独立して選択される1つ又はそれ以上の基で任意に置換され、
lは、0、1、2、3、4、5、又は6であり、
ただし、以下の化合物は包含されない、化合物。
- 各R3が、独立して、水素又はメチルである、請求項1に記載の化合物。
- R1及びR2の1つが、メチル、メトキシ、シクロペンチル、シクロヘキシル、−O−シクロペンチル、−O−シクロヘキシル、フェニル、フェニルオキシであり、又はR1及びR2が一緒になって多環式部分を形成し、前記フェニル、フェニルオキシ、又は多環式部分が、アルキル、アルコキシ、アリール、アリールオキシ、アリールアルキル、アルケニル、及びアルキニルから独立して選択される1つ又はそれ以上の基で任意に置換される、請求項1又は2に記載の化合物。
- R1及びR2が同じである、請求項1から3のいずれか一項に記載の化合物。
- R1及びR2が異なる、請求項1から3のいずれか一項に記載の化合物。
- R1及びR2が任意に置換された多環式部分を形成する、請求項1から3のいずれか一項に記載の化合物。
- m及びnが0である、請求項7に記載の化合物。
- m及びnが、独立して、1又は2である、請求項7に記載の化合物。
- 各R4及びR5が、独立して、C1−C4アルキル、C1−C4アルコキシ、フェニル、フェニルオキシ、ベンジル、C2−C6アルケニル、及びC2−C6アルキニルであり、
lが0又は1である、請求項7又は9に記載の化合物。 - 各R4及びR5が、独立して、メチル、エチル、フェニル、ベンジル、フェネチル、メトキシ、エトキシ、エテニル、エチニルである、請求項10に記載の化合物。
- 各R4及びR5が、独立して、フェニル、フェニルオキシ又はベンジルである、請求項10に記載の化合物。
- R4及びR5が同じである、請求項7又は9から12のいずれか一項に記載の化合物。
- R4及びR5が異なる、請求項7又は9から12のいずれか一項に記載の化合物。
- nが1であり、mが1である、請求項7、9から12、又は14のいずれか一項に記載の化合物。
- nが0である、請求項15に記載の化合物。
- R5がベンジルである、請求項7、9から12、14、15、又は16に記載の化合物。
- lが0である、請求項1又は3から17のいずれか一項に記載の化合物。
- lが1である、請求項1又は3から17のいずれか一項に記載の化合物。
- lが2である、請求項1又は3から17のいずれか一項に記載の化合物。
- lが3である、請求項1又は3から17のいずれか一項に記載の化合物。
- 各R3が、独立して、C1−C4アルキル、C3−C6シクロアルキル、又はフェニルであり、各フェニルが、C1−C4アルキル、C1−C4アルコキシ、フェニル、フェニルオキシ、C2−C4アルケニル、及びC2−C4アルキニルから独立して選択される1つ又はそれ以上の基で任意に置換される、請求項19から21のいずれか一項に記載の化合物。
- 各R3が、独立して、メチル、エチル、シクロペンチル、シクロヘキシル、又はフェニルである、請求項22に記載の化合物。
- 前記ラジカル開始剤が、有機過酸化物、アゾビスイソブチロニトリル又は両方を含む、請求項24に記載の方法。
- 前記ラジカル開始剤がジ−tert−ブチルペルオキシドを含む、請求項25に記載の方法。
- 前記反応が溶媒の存在下で起こる、請求項24から26のいずれか一項に記載の方法。
- 前記反応が溶媒の非存在下で起こる、請求項24から26のいずれか一項に記載の方法。
- a)少なくとも1つのエポキシ樹脂、及び
b)請求項1から23のいずれか一項に記載の少なくとも1つの化合物
を含む硬化性組成物。 - 前記少なくとも1つのエポキシ樹脂が、芳香族エポキシ樹脂、脂環式エポキシ樹脂、脂肪族エポキシ樹脂、及びそれらの組み合わせを含む、請求項29に記載の硬化性組成物。
- 少なくとも1つのエポキシ樹脂が、ジビニルアレーンジオキシド、ビスフェノールAのジグリシジルエーテル、ブロモビスフェノールAのジグリシジルエーテル、ビスフェノールAのオリゴマー又はポリマーのジグリシジルエーテル、テトラブロモビスフェノールAのオリゴマー又はポリマーのジグリシジルエーテル、ビスフェノールF又はその誘導体のジグリシジルエーテル、エポキシノボラック樹脂、エポキシクレゾールノボラック樹脂、又はこれらの混合物である、請求項30に記載の硬化性組成物。
- 少なくとも1つのエポキシ樹脂が、ポリフェノールのグリシジルエーテル化合物であり、前記ポリフェノールが、ヒドロキノン、レゾルシノール、ビスフェノールA、ビスフェノールF、4,4’−ジヒドロキシビフェニル、フェノールノボラック、クレゾールノボラック、トリスフェノール(トリス−(4−ヒドロキシフェニル)メタン)、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン、テトラブロモビスフェノールA、2,2−ビス(4−ヒドロキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン、1,6−ジヒドロキシナフタレン、及びそれらの組み合わせからなる群から選択される、請求項30に記載の硬化性組成物。
- 少なくとも1つのエポキシ樹脂が、少なくとも1つの脂環式環を有するポリオールのポリグリシジルエーテル、又はシクロヘキセン環又はシクロペンテン環を含む化合物を酸化剤でエポキシ化することにより得られるシクロヘキセンオキシド又はシクロペンテンオキシドを含む化合物からなる群から選択される脂環式エポキシ樹脂である、又は
前記少なくとも1つのエポキシ樹脂が、水素化ビスフェノールAジグリシジルエーテル、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキシルカルボキシレート、3,4−エポキシ−1−メチルシクロヘキシル−3,4−エポキシ−1−メチルヘキサンカルボキシレート、6−メチル−3,4−エポキシシクロヘキシルメチル−6−メチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−3−メチルシクロヘキシルメチル−3,4−エポキシ−3−メチルシクロヘキサンカルボキシレート、3,4−エポキシ−5−メチルシクロヘキシルメチル−3,4−エポキシ−5−メチルシクロヘキサンカルボキシレート、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、メチレン−ビス(3,4−エポキシシクロヘキサン)、2,2−ビス(3,4−エポキシシクロヘキシル)プロパン、ジシクロペンタジエンジエポキシド、エチレン−ビス(3,4−エポキシシクロヘキサンカルボキシレート)、ジオクチルエポキシヘキサヒドロフタレート、ジ−2−エチルヘキシルエポキシヘキサヒドロフタレート、及びそれらの組み合わせを含む、請求項30に記載の硬化性組成物。 - 少なくとも1つのエポキシ樹脂が、脂肪族ポリオールのポリグリシジルエーテル又はそのアルキレンオキシド付加物、脂肪族長鎖多塩基酸のポリグリシジルエステル、アクリル酸グリシジル又はメタクリル酸グリシジルのビニル重合によって合成されたホモポリマー、及びアクリル酸グリシジル又はメタクリル酸グリシジルと他のビニルモノマーのビニル重合により合成されたコポリマーからなる群から選択される脂肪族エポキシ樹脂である、請求項30に記載の硬化性組成物。
- 前記ジビニルアレーンジオキシドが、置換ジビニルベンゼンジオキシド、ジビニルナフタレンジオキシド、ジビニルビフェニルジオキシド、ジビニルジフェニルエーテルジオキシド、及びそれらの混合物からなる群から選択される、請求項31に記載の硬化性組成物。
- 前記組成物が、ベンゾオキサジン、スチレン無水マレイン酸コポリマー、フェノールノボラック、シアン酸エステル又はそれらの混合物をさらに含む、請求項29から35のいずれか一項に記載の硬化性組成物。
- 前記エポキシ樹脂が、前記硬化性組成物の総重量に基づいて1重量%〜70重量%の範囲の量で存在する、請求項29から36のいずれか一項に記載の硬化性組成物。
- 請求項1から23のいずれか一項に記載のリン含有化合物が、前記組成物の総重量に基づいて10重量%〜70重量%の範囲の量で存在する、請求項29から37のいずれか一項に記載の硬化性組成物。
- 前記組成物が、天然シリカ、溶融シリカ、球状シリカ、アルミナ、水和アルミナ、タルク、アルミナ三水和物、水酸化マグネシウム及びそれらの組み合わせからなる群から選択される充填剤をさらに含む、請求項29から38のいずれか一項に記載の硬化性組成物。
- 請求項29から39のいずれか一項に記載の硬化性組成物から調製されたプリプレグ。
- 強化成分をさらに含む、請求項40に記載のプリプレグ。
- 前記強化成分が、繊維、布地、又はそれらの組み合わせを含む、請求項41に記載のプリプレグ。
- 請求項29から39のいずれか一項に記載の硬化性組成物から調製された電気的ラミネート。
- 請求項43に記載の電気的ラミネートから調製されたプリント回路基板。
- 前記電気的ラミネートが、プリプレグと導電性材料との交互の層を含む、請求項43に記載の電気的ラミネート。
- 請求項29から39のいずれか一項に記載の組成物及び少なくとも1つの硬化剤を含む硬化性エポキシ樹脂組成物。
- 前記組成物が0.01重量%〜90重量%の硬化剤を含む、請求項46に記載の硬化性組成物。
- 前記硬化剤が、無水物、カルボン酸、アミン化合物、フェノール化合物、ポリオール及びそれらの混合物からなる群から選択される、請求項46又は47のいずれか一項に記載の硬化性組成物。
- (i)請求項29から39のいずれか一項に記載の組成物、及び(ii)少なくとも1つの硬化剤を混合することを含む、硬化性エポキシ樹脂組成物の調製プロセス。
- 請求項29から39又は46から48のいずれか一項に記載の硬化性エポキシ樹脂組成物を硬化させることにより調製される硬化された熱硬化性生成物。
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