JPWO2016121750A1 - 難燃性エポキシ樹脂組成物、それを用いてなるプリプレグ及び積層板 - Google Patents
難燃性エポキシ樹脂組成物、それを用いてなるプリプレグ及び積層板 Download PDFInfo
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- JPWO2016121750A1 JPWO2016121750A1 JP2016572053A JP2016572053A JPWO2016121750A1 JP WO2016121750 A1 JPWO2016121750 A1 JP WO2016121750A1 JP 2016572053 A JP2016572053 A JP 2016572053A JP 2016572053 A JP2016572053 A JP 2016572053A JP WO2016121750 A1 JPWO2016121750 A1 JP WO2016121750A1
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- Prior art keywords
- epoxy resin
- group
- atom
- resin composition
- alkyl group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 108
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 108
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 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 title claims abstract description 22
- 239000003063 flame retardant Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 40
- 239000011574 phosphorus Substances 0.000 claims abstract description 40
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000004429 atom Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 239000000463 material Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000011888 foil Substances 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 238000010030 laminating Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000012784 inorganic fiber Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- -1 phosphorus compound Chemical class 0.000 description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
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- 229920003986 novolac Polymers 0.000 description 21
- 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 20
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000003700 epoxy group Chemical group 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 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 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000005266 casting Methods 0.000 description 10
- 239000003085 diluting agent Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 230000007613 environmental effect Effects 0.000 description 8
- 239000000565 sealant Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 238000013329 compounding Methods 0.000 description 7
- 239000011256 inorganic filler Substances 0.000 description 7
- 229910003475 inorganic filler Inorganic materials 0.000 description 7
- 239000005011 phenolic resin Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000005350 fused silica glass Substances 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KGENPKAWPRUNIG-UHFFFAOYSA-N 1-[chloro(ethyl)phosphoryl]ethane Chemical compound CCP(Cl)(=O)CC KGENPKAWPRUNIG-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000004848 polyfunctional curative Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 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 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229930003836 cresol Natural products 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 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 4
- 239000001993 wax Substances 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 229910002026 crystalline silica Inorganic materials 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
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- 239000003365 glass fiber Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- LTPBRCUWZOMYOC-UHFFFAOYSA-N Beryllium oxide Chemical compound O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
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- 230000008018 melting Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 1
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
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- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
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- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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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- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明の第二の目的は、環境適正に優れると共に硬化物の物性や耐熱性にも優れた、積層板を提供することにある。
本発明のエポキシ樹脂組成物の使用用途は特に限定されるものではなく、例えば、電子回路基板に用いられる積層板、電子部品に用いられる封止剤、注型材、フィルム材、接着剤、電気絶縁塗料、難燃性の必要な複合材、及び粉体塗料等に使用することができる。本発明においては、特に電子回路基板に用いられる積層板、電子部品に用いられる封止剤、及び注型材等に使用することが好ましく、積層板に使用することが最も好ましい。
具体的には、積層板の用途に関しては、フェノール樹脂類又は潜在性硬化剤を使用することが好ましく、フェノールノボラック樹脂、クレゾールノボラック樹脂、又はジシアンジアミド型潜在性硬化剤を使用することがより好ましい。封止剤に関しては、潜在性硬化剤又は酸無水物類を使用することが好ましく、注型材の用途に関しては、脂肪族アミン、芳香族アミン、又は酸無水物類を使用することが好ましい。これらの硬化剤は単独で使用してもよく、2種以上を併用しても良い
但し、上記式(1)中のmは2〜10の整数を表し、R1及びR2はそれぞれ独立に、アルキル基、又はアリール基を表し、R3は、酸素原子、硫黄原子、又は窒素原子を含んでも良い炭化水素基、Xは酸素原子又は硫黄原子、Yは、酸素原子、硫黄原子、又は―NR4―を表し、ここでR4は、水素原子、アルキル基、又はアリール基を表す。
但し、上記式(3)中のmは2〜10の整数を表し、R1及びR2はそれぞれ独立に、アルキル基又はアリール基を表し、R3は、酸素原子、硫黄原子、又は窒素原子を含んでも良い炭化水素基、R8はアルキル基又はアリール基、Xは酸素原子又は硫黄原子、Yは、酸素原子、硫黄原子、又は―NR4―を表し、ここでR4は、水素原子、アルキル基、又はアリール基を表す。
本発明においては、これらの中でも、R1及び/又はR2が、炭素数1〜6のアルキル基であることが好ましく、炭素数が2〜5のアルキル基であることがより好ましく、エチル基又はプロピル基であることが最も好ましい。
但し、上記式(2−1)中のR5は、水素原子又は炭素数が1〜4のアルキル基を表す。
但し、上記式(2−3)中のR1及びR2は、それぞれ独立に、アルキル基又はアリール基を表す。
一方、前記(2−2)の構造の場合には、nが0又は1、oが1〜5の整数であり、R1、R2がそれぞれ独立にエチル基又はプロピル基、R6がメチル基であり、R7がメチレン基、エタンジイル基、又はプロパンジイル基であることが好ましい。
このような化合物としては、例えば、下記式(4−1)〜(4−4)で表される化合物が挙げられる。
本発明においては、上記の反応を、−80〜100℃、好ましくは室温〜50℃で、0.5時間〜72時間、好ましくは1時間〜24時間かけて行わせることができる。
上記プリプレグの基材としては、例えば、ガラス繊維や炭素繊維等の無機繊維、ポリイミド、ポリエステル及びテトラフルオロエチレン等の有機繊維、並びにそれらの混合物等の、公知のものを使用することができる。
尚、以下の実施例等における%は、特に記載がない限り質量基準である。また、プリプレグの外観は、目視観察した場合に、均一な外観のものを良好と評価し、外観が不均一な物を不良とした。同様に、プリプレグを用いて加圧硬化させ、両面銅張積層板を作製した後の外観の評価を目視で観察し、均一に硬化しているものを良好とし、不均一に硬化しているものを不良とした。難燃性は、両面銅張積層板の銅箔をエッチングによって除去し、長さ127mm、幅12.7mmに加工した試験片について、UL(Underwriters Laboratories)の“Test for Flammability of Plastic Materials UL 94”に準じて試験をし、下記の様にして判定した。
<判定方法>
試験片を垂直に保ち、下端にバーナーの火を10秒間接炎させた後、炎を取り除き、試験片に着火した火が消える迄の時間を測定した。次に、火が消えると同時に2回目の接炎を10秒間行ない、1回目と同様にして、着火した火が消える迄の時間を測定した。また、落下する火種により、試験片の下に置いた綿が着火するか否かについても同時に評価した。
1回目と2回目の燃焼時間、綿着火の有無等からUL−94V規格にしたがって燃焼ランクを評価した。燃焼ランクはV−0が最高であり、V−1、V−2となるにしたがって難燃性は低下する。但し、V−0〜V−2のランクの何れにも該当しないものはNRとした。
撹拌羽、還流管、温度計、滴下漏斗及びセプタムを備えた500mLの五口フラスコを、十分に乾燥・窒素置換し、4,4’−ビフェノール29.8g(0.16mol)、トリエチルアミン34.4g(0.34mol)、及び超脱水テトラヒドロフラン300mLを仕込んだ。滴下漏斗にジエチルホスフィン酸クロリド47.8g(0.34mol)を仕込み、反応温度が50℃を超えないように滴下した。滴下終了後、一晩攪拌した。反応溶液を分液漏斗に移し、クロロホルム500mL及び飽和炭酸水素ナトリウム水溶液300mLを加えて良く撹拌し、油水分離した後、水層を除去した。有機層を蒸留水200mLで二回水洗し、無水硫酸マグネシウムで乾燥した後、エバポレーターで溶媒を除去し、含リン化合物(I‐1)60.6g(収率96.1%)を得た。
撹拌羽、還流管、温度計、滴下漏斗及びセプタムを備えた500mLの五口フラスコを、十分に乾燥・窒素置換し、HF‐1M(フェノールノボラック樹脂、明和化成株式会社製)34.2g(0.16mol)、トリエチルアミン34.4g(0.34mol)、及び超脱水テトラヒドロフラン300mLを仕込んだ。滴下漏斗にジエチルホスフィン酸クロリド47.8g(0.34mol)を仕込み、反応温度が50℃を超えないように滴下した。滴下終了後、一晩攪拌した。反応溶液を分液漏斗に移し、クロロホルム500mL及び飽和炭酸水素ナトリウム水溶液300mLを加えて良く撹拌し、油水分離した後、水層を除去した。有機層を蒸留水200mLで二回水洗し、無水硫酸マグネシウムで乾燥した後、エバポレーターで溶媒を除去し、含リン化合物(I‐2)66.4g(収率98.3%)を得た。
撹拌羽、還流管、温度計、滴下漏斗及びセプタムを備えた500mLの五口フラスコを、十分に乾燥・窒素置換し、ビスフェノールA45.7g(0.20mol)、トリエチルアミン42.5g(0.42mol)、及び超脱水テトラヒドロフラン300mLを仕込んだ。滴下漏斗にジエチルホスフィン酸クロリド59.0g(0.42mol)を仕込み、反応温度が50℃を超えないように滴下した。滴下終了後、一晩攪拌した。反応溶液を分液漏斗に移し、クロロホルム500mL及び飽和炭酸水素ナトリウム水溶液300mLを加えて良く撹拌し、油水分離した後、水層を除去した。有機層を蒸留水200mLで二回水洗し、無水硫酸マグネシウムで乾燥した後、エバポレーターで溶媒を除去し、含リン化合物(I‐3)78.1g(収率89.4%)を得た。
撹拌羽、還流管、温度計、滴下漏斗及びセプタムを備えた500mLの五口フラスコを、十分に乾燥・窒素置換し、ビスフェノールF32.0g(0.16mol)、トリエチルアミン34.4g(0.34mol)、及び超脱水テトラヒドロフラン300mLを仕込んだ。滴下漏斗にジエチルホスフィン酸クロリド47.8g(0.34mol)を仕込み、反応温度が50℃を超えないように滴下した。滴下終了後、一晩攪拌した。反応溶液を分液漏斗に移し、クロロホルム500mL及び飽和炭酸水素ナトリウム水溶液300mLを加えて良く撹拌し、油水分離した後水層を除去した。有機層を蒸留水200mLで二回水洗し、無水硫酸マグネシウムで乾燥した後、エバポレーターで溶媒を除去し、含リン化合物(I‐4)60.9g(収率93.2%)を得た。
EOCN−104S(クレゾールノボラック型エポキシ樹脂、日本化薬株式会社製)49.1g、HP−350(水酸化アルミニウム、昭和電工株式会社製)60.1g及びSFP−130MC(球状シリカ、電気化学工業株式会社製)60.1gをメチルエチルケトン100gに加え、三本ロールで分散させた。次いで、製造例1で得られた含リン化合物(I−1)15.3gを、メタノール3gに溶解して加えた。更に、EOCN−104S 50.9g、アデカハードナー EH−3636AS(ジシアンジアミド型潜在性硬化剤、株式会社ADEKA製)5g(5phr)、及びメチルエチルケトン100gを追加してディスパーで分散し、樹脂ワニスを作製した。
回転子、還流管、セプタムを備えた100mL三口フラスコを十分に乾燥、窒素置換し、フェノール28.2g(0.30mol)、トリエチルアミン32.4g(0.32mol)、超脱水テトラヒドロフラン300mLを仕込んだ。滴下漏斗にジエチルホスフィン酸クロリド45.0g(0.32mol)を仕込み、反応温度が50℃を超えないように滴下した。滴下終了後、一晩攪拌した。反応溶液を分液漏斗に移し、クロロホルム500mL及び飽和炭酸水素ナトリウム水溶液300mL を加えて良く撹拌し、油水分離後、水層を除去した。有機層を蒸留水200mL で二回水洗し、有機層を無水硫酸マグネシウムで乾燥した後エバポレーターで溶媒を除去し、含リン化合物(I−5)50.7g(収率85.3%)を得た。
表1に記載した組成で配合したこと以外は、実施例1と同様にして両面銅張積層板を作製して各種評価を行った。結果は表1に示した通りである。
*2 FP−600:下記構造式(7)で表される化合物、株式会社ADEKA製
表1の結果から、本発明の難燃性エポキシ樹脂組成物を使用した積層板は、良好な難燃性を示すことが確認された。
Claims (6)
- 前記式(1)中のR3が、芳香環を少なくとも1個有する炭化水素基である、請求項1に記載されたエポキシ樹脂組成物。
- 前記式(1)中のX及びYが共に酸素原子であり、R1及びR2が、それぞれ独立に炭素数1〜4のアルキル基であり、R3が下記一般式(2−1)〜(2−6)から選択される何れかの構造を有する基である、請求項1又は2に記載されたエポキシ樹脂組成物;
但し、上記式(2−1)中のR5は、水素原子又は炭素数が1〜4のアルキル基を表す;
但し、上記式(2−2)中のnは0〜3の整数、oは0〜50の整数を表し、R6は、水素原子又は炭素数が1〜4のアルキル基、R7は、酸素原子又は硫黄原子を含んでもよい炭化水素基を表し、Zは水酸基又は下記一般式(2−3)で表される官能基である;
但し、上記式(2−3)中のR1及びR2は、それぞれ独立に、アルキル基又は下記のアリール基を表す;
- 無機繊維及び有機繊維から選択され得た少なくとも1種の繊維からなるシート状基材と、請求項1に記載されたエポキシ樹脂組成物とからなることを特徴とするプリプレグ。
- 請求項4に記載されたプリプレグ又は2以上の該プリプレグを積層してなる積層体の少なくとも一方の表面に金属箔を配置して積層し、熱圧着することを特徴とするエポキシ樹脂積層板の製造方法。
- 請求項5に記載された方法によって製造されてなるエポキシ樹脂積層板。
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