JPWO2020045150A1 - リン含有エポキシ樹脂、エポキシ樹脂組成物、プリプレグ、積層板、回路基板用材料および硬化物 - Google Patents
リン含有エポキシ樹脂、エポキシ樹脂組成物、プリプレグ、積層板、回路基板用材料および硬化物 Download PDFInfo
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- JPWO2020045150A1 JPWO2020045150A1 JP2020539365A JP2020539365A JPWO2020045150A1 JP WO2020045150 A1 JPWO2020045150 A1 JP WO2020045150A1 JP 2020539365 A JP2020539365 A JP 2020539365A JP 2020539365 A JP2020539365 A JP 2020539365A JP WO2020045150 A1 JPWO2020045150 A1 JP WO2020045150A1
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- Prior art keywords
- epoxy resin
- phosphorus
- resin composition
- type epoxy
- area
- Prior art date
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- Granted
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 228
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 228
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 100
- 239000011574 phosphorus Substances 0.000 title claims abstract description 99
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 239000000463 material Substances 0.000 title claims description 15
- 229920003986 novolac Polymers 0.000 claims abstract description 114
- -1 phosphorus compound Chemical class 0.000 claims abstract description 69
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- 125000000524 functional group Chemical group 0.000 claims abstract description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 116
- 229920005989 resin Polymers 0.000 claims description 51
- 239000011347 resin Substances 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000005011 phenolic resin Substances 0.000 claims description 27
- 239000004593 Epoxy Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 30
- 238000001723 curing Methods 0.000 description 61
- 230000015572 biosynthetic process Effects 0.000 description 35
- 238000003786 synthesis reaction Methods 0.000 description 33
- 238000000034 method Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 24
- 150000001299 aldehydes Chemical class 0.000 description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 22
- 239000003063 flame retardant Substances 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
- 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 19
- 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 19
- 150000002989 phenols Chemical class 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
- 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 12
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 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 10
- 238000009826 distribution Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 8
- 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 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229930192627 Naphthoquinone Natural products 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 150000002791 naphthoquinones Chemical class 0.000 description 7
- 150000002903 organophosphorus compounds Chemical class 0.000 description 7
- 239000000523 sample Substances 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 230000001771 impaired effect Effects 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- 150000004780 naphthols Chemical class 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N beta-hydroxynaphthyl Natural products C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000011256 inorganic filler Substances 0.000 description 4
- 229910003475 inorganic filler Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229960001755 resorcinol Drugs 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000005130 benzoxazines Chemical class 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical class CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- OHBQPCCCRFSCAX-UHFFFAOYSA-N 1,4-Dimethoxybenzene Chemical compound COC1=CC=C(OC)C=C1 OHBQPCCCRFSCAX-UHFFFAOYSA-N 0.000 description 2
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- NWQWQKUXRJYXFH-UHFFFAOYSA-N 2,2-Dichloroacetaldehyde Chemical compound ClC(Cl)C=O NWQWQKUXRJYXFH-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- NMPVEAUIHMEAQP-UHFFFAOYSA-N 2-Bromoacetaldehyde Chemical compound BrCC=O NMPVEAUIHMEAQP-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
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Abstract
Description
本発明のエポキシ樹脂組成物は、リン含有エポキシ樹脂及および硬化剤を必須成分とし、リン含有率が1.0〜1.8質量%の範囲である。本明細書におけるエポキシ樹脂組成物としてのリン含有率とは、エポキシ樹脂組成物から溶剤と無機充填剤を除いた有機成分中における比率を指す。リン含有率が1.0質量%未満の場合、難燃性が不十分となる恐れがあり、リン含有率が1.8質量%を超えるとTg=200℃以上の耐熱性を確保できない恐れがある。好ましい範囲はリン含有率が1.5〜1.8質量%である。
なお、原料モル比に換算すると、例えば、一般式(2)のリン化合物がDOPOであり、一般式(1)のリン化合物がDOPOとナフトキノン(NQ)との反応物である場合、NQ/DOPO(モル比)0.50であるとき、一般式(1)のリン化合物と一般式(2)のリン化合物のモル比は、50:50に相当し、NQ/DOPO(モル比)0.99であるとき、99:1に相当する。
一般式(1)または一般式(2)において、R1およびR2はヘテロ原子を有してもよい炭素数1〜20の炭化水素基を示し、それぞれは異なっていても同一でも良く、直鎖状、分岐鎖状、環状であってもよい。また、R1とR2が結合して環状構造を形成してもよい。特に、ベンゼン環等の芳香族環基が好ましい。R1およびR2が芳香族環基の場合、置換基として、炭素数1〜8のアルキル基、炭素数1〜8のアルコキシ基、炭素数5〜8のシクロアルキル基、炭素数6〜10のアリール基、炭素数7〜11のアラルキル基、炭素数6〜10のアリールオキシ基または炭素数7〜11のアラルキルオキシ基を有してもよい。ヘテロ原子としては、酸素原子等が例示され、これは炭化水素鎖または炭化水素環を構成する炭素間に含まれることができる。
n1およびn2はそれぞれ独立に、0または1である。
Aは3価の炭素数6〜20の芳香族炭化水素基である。好ましくはベンゼン環基やナフタレン環基である。芳香族炭化水素基は、置換基として、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数6〜10のアリール基、炭素数6〜10のアリールオキシ基、炭素数7〜12のアラルキル基、または炭素数7〜12のアラルキルオキシ基を有してもよい。
使用されるフェノール類としてはフェノール、クレゾール、エチルフェノール、ブチルフェノール、スチレン化フェノール、クミルフェノール、ナフトール、カテコール、レゾルシノール、ナフタレンジオール、ビスフェノールAなどが挙げられ、アルデヒド類としてはホルマリン、ホルムアルデヒド、ヒドロキシベンズアルデヒド、サリチルアルデヒドなどが挙げられる。また、アルデヒド類の代わりにキシリレンジメタノール、キシリレンジクロライド、ビスクロロメチルナフタレン、ビスクロロメチルビフェニルなどを使用したアラルキル型フェノール樹脂も本発明ではノボラック型フェノール樹脂に含む。
これら得られた出発原料は、蒸留等の各種手法によって2核体を中心とする低分子量を除去または含有率を10面積%以下まで低減した後、さらに酸触媒存在下で再度アルデヒド類と縮合を行うことによって2核体を減らしながら、かつ7核体以上の比率を増やす調整を行う。ノボラック型エポキシ樹脂はこのノボラック型フェノール樹脂の分子量分布を反映してエポキシ化されるため、得られたノボラック型エポキシ樹脂においても各核体の含有率は同様に調整されたものが得られる。
なお、本明細書において、ノボラック型エポキシ樹脂の各核体の「含有率」はGPC測定による「面積%」のことであり、含有率または面積%と表現する場合がある。また、7核体以上の含有率と3核体の含有率を、それぞれ単に「H」、「L」と表現する場合がある。ここで、上記一般式(3)で表されるノボラック型エポキシ樹脂において、3核体とはnが2の場合であり、7核体以上とはnが6以上の場合である。
ここで(L/H)が4.0を超えると3核体が多くなり、平均官能基数が3.8未満となり、リン含有エポキシ樹脂を使用した硬化物の耐熱性が下がり200℃以上のTgを得ることができない。一方(L/H)が0.6未満の場合は7核体以上が多くなり、2核体も少なくなるため、硬化物が硬脆くなり、難燃性が大きく損なわれる。
アルデヒド類としては、ホルムアルデヒド、アセトアルデヒド、プロピルアルデヒド、ブチルアルデヒド、バレルアルデヒド、カプロンアルデヒド、ベンズアルデヒド、クロルアルデヒド、ブロムアルデヒド、グリオキザール、マロンアルデヒド、スクシンアルデヒド、グルタルアルデヒド、アジピンアルデヒド、ピメリンアルデヒド、セバシンアルデヒド、アクロレイン、クロトンアルデヒド、サリチルアルデヒド、フタルアルデヒド、ヒドロキシベンズアルデヒドなどが挙げられる。
ビフェニル系縮合剤としてビス(メチロール)ビフェニル、ビス(メトキシメチル)ビフェニル、ビス(エトキシメチル)ビフェニル、ビス(クロロメチル)ビフェニルなどが挙げられる。
ホウ酸エステルとしては、トリブチルボレ−ト、トリメトキシボロキシン、ホウ酸エチル、エポキシ−フェノール−ホウ酸エステル配合物(例えば、キュアダクトL−07N(四国化成工業株式会社製)など)などが挙げられ、アルキルリン酸エステルとしては、リン酸トリメチル、リン酸トリブチルなどが挙げられる。
反応遅延剤は単独でも複数を混合して使用してもよいが、使用量の調整のしやすさから単独が好ましく、とりわけホウ酸が少量の使用でその効果が最も良好である。使用の際はメタノールやブタノール、2−プロパノールなどのアルコール系溶剤に溶解して5〜20質量%の濃度で使用することができる。特に硬化剤がジシアンジアミドの場合は、硬化剤1モルに対してホウ酸0.1〜0.5モルが好ましく、0.15〜0.35モルが、遅延効果と耐熱性を得る上でより好ましい。また硬化剤がフェノール系硬化剤の場合は、リン含有エポキシ樹脂に対して0.1〜5質量部が好ましく、0.1〜1質量部が耐熱性を得る上でより好ましい。特に、ホウ酸使用量が5質量部以上に増えると、硬化性を調整する上でイミダゾールなどの反応促進剤の量を増やす必要があり、硬化物での絶縁信頼性を著しく損なうために好ましくない。
撹拌機、温度調節装置、還流冷却器、全縮器、減圧装置などを備えた4つ口のガラス製セパラブルフラスコに、フェノールを1000部加えて80℃まで昇温した後、2.8部のシュウ酸2水和物を添加して撹拌溶解し、142部の37.5%ホルマリンを30分間かけて滴下した。その後、反応温度を92℃に維持して3時間反応を行った。反応終了後、110℃まで温度を上げて脱水した後、残存するフェノールを150℃、60mmHgの回収条件で約90%回収した後、5mmHgの回収条件で回収した後、さらに160℃、80mmHgの条件下で水10部を90分間かけて滴下して残存するフェノールを除去した後、溶融しているフェノールノボラック樹脂中に窒素ガスを60分間バブリングして、フェノールノボラック樹脂(N0)を得た。
得られたN0を280℃、5mmHgの薄膜蒸留器を使用して2核体の一部をさらに留出除去してフェノールノボラック樹脂(N1)を得た。得られたN1は軟化点65℃で、2核体10.8面積%、3核体52.9面積%、4核体21.8面積%、5核体8.5面積%、6核体6.0面積%、実平均分子量は355であった。
合成例1で得たN0を使用して300℃、5mmHgの薄膜蒸留器を使用して2核体の一部をさらに強く留出除去してフェノールノボラック樹脂(N2)を得た。得られたN2は軟化点66℃で、2核体5.9面積%、3核体58.4面積%、4核体22.9面積%、5核体8.3面積%、6核体4.6面積%、実平均分子量は356であった。
撹拌機、温度調節装置、還流冷却器、全縮器、窒素ガス導入装置、減圧装置および滴下装置を備えた4つ口のガラス製セパラブルフラスコに、合成例1で得られたN1を1000部、シュウ酸二水和物0.38部を仕込み、窒素ガスを導入しながら撹拌を行い、加熱を行って昇温した。37.5%ホルマリン13.5部を80℃で滴下を開始し30分で滴下を終了した。その後、反応温度を92℃に保ち3時間反応を行い次いで110℃まで昇温して反応生成水を系外に除去した。最後に160℃下で2時間の加温を行い、フェノールノボラック樹脂(N3)を得た。得られたN3は軟化点63℃で、2核体9.4面積%、3核体48.1面積%、7核体以上9.0面積%、Mn552であった。
N1を1000部、シュウ酸二水和物を0.63部、37.5%ホルマリンを22.5部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N4)を得た。得られたN4は軟化点69℃で、2核体8.0面積%、3核体43.7面積%、7核体以上14.2面積%、Mn574であった。その後、合成例3と同様に、N4のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E2)を得た。
N1を1000部、シュウ酸二水和物を1.89部、37.5%ホルマリンを67.6部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N5)を得た。得られたN5は軟化点78℃で、2核体7.2面積%、3核体31.2面積%、7核体以上30.9面積%、Mn690であった。その後、合成例3と同様に、N5のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E3)を得た。
N2を1000部、シュウ酸二水和物を0.63部、37.5%ホルマリンを22.5部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N6)を得た。得られたN6は軟化点70℃で、2核体5.1面積%、3核体45.8面積%、7核体以上14.4面積%、Mn589であった。その後、合成例3と同様に、N6のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E4)を得た。
LV−70S(群栄化学工業株式会社製フェノールノボラック樹脂、軟化点65℃、2核体1.0面積%、3核体74.7面積%、4核体18.1面積%、5核体6.2面積%、実測数平均分子量337)を1000部、シュウ酸二水和物を0.66部、37.5%ホルマリンを23.7部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N7)を得た。得られたN7は軟化点67℃で、2核体1.1面積%、3核体57.3面積%、6核体と7核体の分離は困難であり6核体以上の含有率が22.0面積%、Mn580であった。その後、合成例3と同様に、N7のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E5)を得た。
N1を1000部、シュウ酸二水和物を0.32部、37.5%ホルマリンを11.3部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N8)を得た。得られたN8は軟化点62℃で、2核体9.6面積%、3核体48.4面積%、7核体以上7.7面積%、Mn545であった。その後、合成例3と同様に、N8のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E6)を得た。
N1を1000部、シュウ酸二水和物を2.52部、37.4%ホルマリンを90.1部の仕込み以外は、合成例3と同様にしてフェノールノボラック樹脂(N9)を得た。得られたN9は軟化点84℃で2核体5.7面積%、3核体24.1面積%、7核体以上41.5面積%、Mn748であった。その後、合成例3と同様に、N9のエポキシ化を行って、フェノールノボラック型エポキシ樹脂(E7)を得た。
YDPN−638(フェノールノボラック型エポキシ樹脂、日鉄ケミカル&マテリアル株式会社製、エポキシ当量178)とYDF−170(ビスフェノールF型液状エポキシ樹脂、日鉄ケミカル&マテリアル株式会社製、エポキシ当量168)を1/1(質量比)で溶融混同して、フェノールノボラック型エポキシ樹脂(E11)を得た。
E1:合成例3で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量171、Mn650、3核体40.6面積%、7核体以上20.9面積%)
E2:合成例4で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量172、Mn682、3核体36.4面積%、7核体以上26.7面積%)
E3:合成例5で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量173、Mn824、3核体26.1面積%、7核体以上42.2面積%)
E4:合成例6で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量174、Mn693、3核体38.8面積%、7核体以上26.0面積%)
E5:合成例7で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量173、Mn669、3核体48.9面積%、7核体以上14.6面積%)
E6:合成例8で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量171、Mn623、3核体41.9面積%、7核体以上19.9面積%)
E7:合成例9で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量175、Mn858、3核体20.7面積%、7核体以上48.5面積%)
E8:フェノールノボラック型エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YDPN−6300、エポキシ当量175、Mn653、3核体35.2面積%、7核体以上21.8面積%)
E9:フェノールノボラック型エポキシ樹脂(日鉄ケミカル&マテリアル株式会社製、YDPN−638、エポキシ当量178、Mn662、3核体14.7面積%、7核体以上38.6面積%)
E10:フェノールノボラック型エポキシ樹脂(DIC株式会社製、N775、エポキシ当量187、Mn1308、3核体6.7面積%、7核体以上71.6面積%)
E11:合成例10で得られたフェノールノボラック型エポキシ樹脂(エポキシ当量173、Mn468、3核体12.1面積%、7核体以上19.3面積%)
E12:3官能エポキシ樹脂(三井化学株式会社製、VG−3101、エポキシ当量219)
B1:ジシアンジアミド(日本カーバイド株式会社製、ジシアンジアミド、活性水素当量21)
B2:トリアジン環およびヒドロキシフェニル基含有化合物(群栄化学工業株式会社製、PS−6313、活性水素当量148)
B3:アラルキル型多価フェノール樹脂(日鉄ケミカル&マテリアル株式会社製、NX−1723、活性水素当量152)
B4:トリスフェニルメタン型多価フェノール樹脂(明和化成工業株式会社製、MEH−7500H、活性水素当量100)
B5:フェノールノボラック樹脂(群栄化学工業株式会社製、レヂトップPSM−6358、軟化点118℃、活性水素当量106)
B6:ベンゾオキサジン樹脂(日鉄ケミカル&マテリアル株式会社製、YBZ−2213、軟化点75℃、活性水素当量217)
B7:ベンゾオキサジン樹脂(ハンツマン社製、LMB6490、軟化点98℃、活性水素当量276)
B8:ベンゾオキサジン樹脂(四国化成工業株式会社製、F−a型、軟化点61℃、活性水素当量212)
C1:2−エチル−4−メチルイミダゾール(硬化促進剤、四国化成工業株式会社製、キュアゾール2E4MZ)
FR1:シクロホスファゼン(非ハロゲン難燃剤、株式会社伏見製薬所製、ラビトルFP−100、リン含有率13%)
FR2:水酸化マグネシウム(非ハロゲン難燃剤、充填剤、協和化学工業株式会社製、キスマ5、平均粒子径:約0.8〜1.0μm)
撹拌機、温度調節装置、還流冷却器、全縮器、窒素ガス導入装置を備えた4つ口のガラス製セパラブルフラスコに、HCA(三光株式会社製、DOPO)100部とトルエン185部を仕込み、80℃で加温溶解した。その後、1,4−ナフトキノン(NQ)62.2部を反応熱による昇温に注意しながら分割投入した。このときNQとDOPOのモル比(NQ/DOPO)は0.85であった。この反応後、エポキシ樹脂E1を627部仕込み、窒素ガスを導入しながら撹拌を行い、130℃まで加熱を行って溶解した。トリフェニルホスフィン(TPP)を0.08部添加して150℃で4時間反応した後、メトキシプロパノールを42部投入して140℃でさらに2時間反応を行って、リン含有エポキシ樹脂(PE1)を得た。
表1の配合量(部)で配合し、実施例1と同様の操作を行い、リン含有エポキシ樹脂を得た。リン含有エポキシ樹脂の物性値を表1に示した。なお、「反応率」は、実測エポキシ当量から計算で求めた原料リン化合物の消費率を表し、「L/H」は使用したフェノールノボラック型エポキシ樹脂の7核体以上の含有率(面積%、H)に対する3核体の含有率(面積%、L)の比を表し、「Mn/E」は平均官能基数を表す。
表2の配合量(部)で配合し、実施例1と同様の操作を行い、リン含有エポキシ樹脂を得た。リン含有エポキシ樹脂の物性値を表2に示した。
リン含有エポキシ樹脂(PE1)を100部、硬化剤(B1)を3.7部、10%ホウ酸メタノール溶液を0.5部配合した。配合の際にエポキシ樹脂はメチルエチルケトンで溶解したワニスの状態で仕込み、硬化剤はメトキシプロパノールとN,N−ジメチルホルムアミドの混合溶媒に溶解して配合し、メチルエチルケトン、メトキシプロパノールにて不揮発分を50%となるように調整した。その後、このワニスでのゲルタイムが171℃下で150〜350秒になるように、硬化促進剤(2E4MZ)のメトキシプロパノール溶液を使用して調整を行って、リン含有エポキシ樹脂組成物ワニスを得た。
表3の配合量(部)で配合し、実施例9と同様の操作を行い、積層板を得た。実施例9と同様の試験を行い、その結果を表3に示す。
表4の配合量(部)で配合し、実施例9と同様の操作を行い、積層板を得た。実施例9と同様の試験を行い、その結果を表4に示す。
表5の配合量(部)で配合し、実施例9と同様の操作を行い、リン含有エポキシ樹脂組成物ワニスを得た後、ホモディスパーを使用して、FR1やFR2を5000rpmのせん断撹拌をしながら分割投入し、約10分間の均一分散を行った。硬化温度条件を210℃×80分に変更した以外は実施例9と同様の操作を行い、積層板試験片を得た。実施例9と同様の試験を行い、その結果を表5に示す。
Claims (8)
- リン含有エポキシ樹脂と硬化剤を含み、リン含有率が1.0〜1.8質量%の範囲であるエポキシ樹脂組成物であって、リン含有エポキシ樹脂は、ゲルパーミネーションクロマトグラフィー測定による7核体以上の含有率(面積%、H)に対する3核体の含有率(面積%、L)の比(L/H)が0.6〜4.0の範囲であり、かつ標準ポリスチレン換算値による数平均分子量(Mn)をエポキシ当量(E)で除した平均官能基数(Mn/E)が3.8〜4.8の範囲であるノボラック型エポキシ樹脂と、下記一般式(1)および/または一般式(2)で表されるリン化合物とから得られた生成物であることを特徴とするエポキシ樹脂組成物。
- ノボラック型エポキシ樹脂がフェノールノボラック型エポキシ樹脂である請求項1に記載のエポキシ樹脂組成物。
- 硬化剤がジシアンジアミド、フェノール樹脂およびオキサジン樹脂から選択される一種または二種以上を含む請求項1に記載のエポキシ樹脂組成物。
- 請求項1〜3のいずれか1項に記載のエポキシ樹脂組成物を基材に含浸してなるプリプレグ。
- 請求項1〜3のいずれか1項に記載のエポキシ樹脂組成物を硬化してなる積層板。
- 請求項1〜3のいずれか1項に記載のエポキシ樹脂組成物を使用して得られる回路基板用材料。
- 請求項1〜3のいずれか1項に記載のエポキシ樹脂組成物を硬化してなる硬化物。
- ノボラック型エポキシ樹脂と、下記一般式(1)および/または一般式(2)で表されるリン化合物とから得られるリン含有エポキシ樹脂の製造方法であって、ノボラック型エポキシ樹脂が、ゲルパーミネーションクロマトグラフィー測定による7核体以上の含有率(面積%、H)に対する3核体の含有率(面積%、L)の比(L/H)が0.6〜4.0の範囲であり、かつ標準ポリスチレン換算値による数平均分子量(Mn)をエポキシ当量(E)で除した平均官能基数(Mn/E)が3.8〜4.8の範囲であることを特徴とするリン含有エポキシ樹脂の製造方法。
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