JPWO2018008414A1 - エポキシ樹脂とその硬化物 - Google Patents
エポキシ樹脂とその硬化物 Download PDFInfo
- Publication number
- JPWO2018008414A1 JPWO2018008414A1 JP2017562781A JP2017562781A JPWO2018008414A1 JP WO2018008414 A1 JPWO2018008414 A1 JP WO2018008414A1 JP 2017562781 A JP2017562781 A JP 2017562781A JP 2017562781 A JP2017562781 A JP 2017562781A JP WO2018008414 A1 JPWO2018008414 A1 JP WO2018008414A1
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- Prior art keywords
- epoxy resin
- epoxy
- compound
- mass
- 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 91
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 150000004820 halides Chemical class 0.000 claims abstract description 27
- 239000011342 resin composition Substances 0.000 claims abstract description 25
- 239000004593 Epoxy Substances 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 239000002253 acid Substances 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 239000004065 semiconductor Substances 0.000 claims abstract description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003566 sealing material Substances 0.000 claims abstract description 12
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 34
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- 239000000463 material Substances 0.000 description 11
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- 125000001424 substituent group Chemical group 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
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- 229930185605 Bisphenol Natural products 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 3
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
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- 239000004744 fabric Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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- 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 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
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 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 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- XFSBVAOIAHNAPC-WSORPINJSA-N acetylbenzoylaconine Chemical compound O([C@H]1[C@]2(O)C[C@H]3C45[C@@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)C4[C@]([C@@H](C[C@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-WSORPINJSA-N 0.000 description 2
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
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- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 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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- 238000009835 boiling Methods 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
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- 239000011810 insulating material Substances 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- KHARCSTZAGNHOT-UHFFFAOYSA-N naphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 KHARCSTZAGNHOT-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 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 1
- 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 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000001721 transfer moulding Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4284—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with other curing agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4223—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aromatic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
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Abstract
Description
本発明のエポキシ樹脂は、フェノール性水酸基含有化合物(a1)と芳香族ジカルボン酸又はその酸ハロゲン化物(a2)とのエステル化物(A)と、2官能エポキシ化合物(B)とを必須の反応原料とすることを特徴とする。
[式(2−1)〜(2−17)中、R1は炭素原子数2〜10の脂肪族炭化水素基或いはその炭素原子上にアルコキシ基又はハロゲン原子を一つ乃至複数有する構造部位である。R2、R3はそれぞれ独立に脂肪族炭化水素基、アルコキシ基、ハロゲン原子、アリール基、アラルキル基の何れかである。kは1〜4の整数、lは0又は1〜4の整数、mは0又は1〜6の整数、pは0又は1〜3の整数、qは0又は1〜5の整数である。Ar1は置換基を有してもよいアリール基、Ar2は置換基を有してもよいモノヒドロキシアリール基を表す。式(2−13)、(2−14)中xとyとは互いに隣接する炭素原子に結合し、それぞれキサンテン構造又はジナフトフラン構造を形成する。式(2−17)中Zは炭化水素基、酸素原子、カルボニル基の何れかである。]
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G4000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC−WorkStation」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8320」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)
測定装置 :東ソー株式会社製「HLC−8320 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G4000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPCワークステーション EcoSEC−WorkStation」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8320」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、イソフタル酸クロリド202質量部とトルエン1250質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、1−ナフトール288質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、テトラブチルアンモニウムブロマイド0.6質量部を加え、窒素ガスパージを施しながら、系内を60℃以下に制御して、20%水酸化ナトリウム水溶液400質量部を3時間かけて滴下した。滴下終了後、そのまま1時間撹拌を続けて反応させた。反応終了後、反応混合物を静置して分液し、水層を取り除いた。残った有機層に水を加えて約15分間攪拌混合した後、混合物を静置して分液し、水層を取り除いた。水層のpHが7になるまでこの操作を繰り返した後、加熱減圧乾燥して、下記構造式(a)で表されるエステル化物(A−1)395質量部を得た。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、ジヒドロキシナフタレン型エポキシ樹脂(DIC株式会社製「HP−4032D」エポキシ基当量141g/当量)72質量部、先で得たエステル化物(A−1)105質量部、シクロヘキサノン76質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、ジメチルアミノピリジン0.07質量部を加え、窒素ガスパージを施しながら、系内を150℃まで加温した。150℃で12時間反応させた後、シクロヘキサノン130質量部とメチルエチルケトン206質量部とを加えて希釈し、エポキシ樹脂(1)溶液549質量部を得た。エポキシ樹脂(2)のエポキシ基当量は34,860g/当量、重量平均分子量(Mw)は23,940、分子量分布(Mw/Mn)は6.8であった。得られたエポキシ樹脂(2)のGPCチャートを図2に示す。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、脂環式エポキシ樹脂(ダイセル株式会社製「CEL2021P」エポキシ基当量130g/当量)66質量部、先で得たエステル化物(A−1)105質量部、シクロヘキサノン73質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、ジメチルアミノピリジン0.07質量部を加え、窒素ガスパージを施しながら、系内を150℃まで加温した。150℃で12時間反応させた後、シクロヘキサノン126質量部とメチルエチルケトン199質量部とを加えて希釈し、エポキシ樹脂(3)溶液532質量部を得た。エポキシ樹脂(3)のエポキシ基当量は8,210g/当量、重量平均分子量(Mw)は10,000、分子量分布(Mw/Mn)は5.7であった。得られたエポキシ樹脂(3)のGPCチャートを図3に示す。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、下記構造式(b)で表されるキサンテン型エポキシ化合物を主成分とするエポキシ樹脂(エポキシ基当量265g/当量)136質量部、先で得たエステル化物(A−1)105質量部、シクロヘキサノン103質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、ジメチルアミノピリジン0.10質量部を加え、窒素ガスパージを施しながら、系内を150℃まで加温した。150℃で12時間反応させた後、シクロヘキサノン178質量部とメチルエチルケトン281質量部とを加えて希釈し、エポキシ樹脂(4)溶液750質量部を得た。エポキシ樹脂(4)のエポキシ基当量は8,520g/当量、重量平均分子量(Mw)は23,530、分子量分布(Mw/Mn)は8.3であった。得られたエポキシ樹脂(4)のGPCチャートを図4に示す。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、下記構造式(c)で表されるフルオレン型エポキシ樹脂を主成分とするエポキシ樹脂(エポキシ基当量246g/当量)127質量部、先で得たエステル化物(A−1)105質量部、シクロヘキサノン99質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、ジメチルアミノピリジン0.09質量部を加え、窒素ガスパージを施しながら、系内を150℃まで加温した。150℃で12時間反応させた後、シクロヘキサノン171質量部とメチルエチルケトン270質量部とを加えて希釈し、エポキシ樹脂(5)溶液738質量部を得た。エポキシ樹脂(5)のエポキシ基当量は13,270g/当量、重量平均分子量(Mw)は21,000、分子量分布(Mw/Mn)は5.8であった。得られたエポキシ樹脂(5)のGPCチャートを図5に示す。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、ビスフェノールA型エポキシ樹脂(DIC株式会社製「EPICLON 850−S」エポキシ基当量188g/当量)97質量部、ビスフェノールAジベンゾイル化物109質量部、シクロヘキサノン88質量部を仕込み、系内を減圧窒素置換して溶解させた。次いで、ジメチルアミノピリジン0.08質量部を加え、窒素ガスパージを施しながら、系内を150℃まで加温した。150℃で36時間反応させた後、シクロヘキサノン152質量部とメチルエチルケトン240質量部とを加えて希釈し、エポキシ樹脂(1’)溶液650質量部を得た。エポキシ樹脂(1’)のエポキシ基当量は6,650g/当量、重量平均分子量(Mw)は7,380、分子量分布(Mw/Mn)は2.3であった。
フィルムの作成、評価
実施例1〜5及び比較製造例1で得たエポキシ樹脂溶液をセパレータ(シリコーン処理したポリエチレンテレフタレートフィルム)上にアプリケータで塗布し、80℃で10分、更に150℃で1時間乾燥させ、厚さ70μmのエポキシ樹脂フィルムを作成した。フィルムの形状を保持出来るものはA、保持出来ないものはBと判断した。
上記で作成したエポキシ樹脂フィルムをMETTLER TOLEDO社製DSC822eを用いて、10℃/minの条件でDSC−Tgを測定した。
得られたエポキシ樹脂フィルムを加熱真空乾燥後、23℃、湿度50%の室内に24時間保管した。その後、JIS−C−6481に準拠し、アジレント・テクノロジー株式会社製インピーダンス・マテリアル・アナライザ「HP4291B」を用いて、エポキシ樹脂フィルムの1GHzでの誘電正接を測定した。
Claims (7)
- フェノール性水酸基含有化合物(a1)と芳香族ジカルボン酸又はその酸ハロゲン化物(a2)とのエステル化物(A)と、2官能エポキシ化合物(B)とを必須の反応原料とすることを特徴とするエポキシ樹脂。
- エポキシ基当量が5,000〜100,000g/当量の範囲である請求項1記載のエポキシ樹脂。
- 重量平均分子量(Mw)が5,000〜100,000の範囲である請求項1記載のエポキシ樹脂。
- 請求項1〜3の何れか一つに記載のエポキシ樹脂を含有する硬化性樹脂組成物。
- 請求項4記載の硬化性樹脂組成物の硬化物。
- 請求項4記載の硬化性組成物を用いてなるプリント配線基板。
- 請求項4記載の硬化性組成物を用いてなる半導体封止材料。
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