WO2021039558A1 - フェノール樹脂、硬化性樹脂組成物及びその硬化物 - Google Patents
フェノール樹脂、硬化性樹脂組成物及びその硬化物 Download PDFInfo
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- WO2021039558A1 WO2021039558A1 PCT/JP2020/031384 JP2020031384W WO2021039558A1 WO 2021039558 A1 WO2021039558 A1 WO 2021039558A1 JP 2020031384 W JP2020031384 W JP 2020031384W WO 2021039558 A1 WO2021039558 A1 WO 2021039558A1
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- Prior art keywords
- resin
- resin composition
- phenol
- compound
- group
- Prior art date
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- 239000005011 phenolic resin Substances 0.000 title claims abstract description 91
- 229920001568 phenolic resin Polymers 0.000 title claims abstract description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000011342 resin composition Substances 0.000 title claims description 74
- -1 monophenol compound Chemical class 0.000 claims abstract description 125
- 239000000463 material Substances 0.000 claims abstract description 36
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 229920005989 resin Polymers 0.000 claims description 109
- 239000011347 resin Substances 0.000 claims description 109
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 73
- 239000000047 product Substances 0.000 claims description 44
- 239000003822 epoxy resin Substances 0.000 claims description 40
- 229920000647 polyepoxide Polymers 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 21
- 238000005259 measurement Methods 0.000 claims description 21
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- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000000468 ketone group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 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 9
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- 229930003836 cresol Natural products 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
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- 229910003475 inorganic filler Inorganic materials 0.000 claims description 7
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- 239000011889 copper foil Substances 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
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- 150000001875 compounds Chemical class 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 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 18
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000002156 mixing Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
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- 239000002184 metal Substances 0.000 description 11
- 229920000877 Melamine resin Polymers 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 7
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- 238000010438 heat treatment Methods 0.000 description 7
- 238000010030 laminating Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000008393 encapsulating agent Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
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- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
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- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
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- 239000002798 polar solvent Substances 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 238000007788 roughening Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 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
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DKMKZSWJCOWHSD-UHFFFAOYSA-N sulfuric acid;triazin-4-amine Chemical class OS(O)(=O)=O.NC1=CC=NN=N1 DKMKZSWJCOWHSD-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000002383 tung oil Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide 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
- IPCXNCATNBAPKW-UHFFFAOYSA-N zinc;hydrate Chemical compound O.[Zn] IPCXNCATNBAPKW-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- QSGNKXDSTRDWKA-UHFFFAOYSA-N zirconium dihydride Chemical compound [ZrH2] QSGNKXDSTRDWKA-UHFFFAOYSA-N 0.000 description 1
- 229910000568 zirconium hydride Inorganic materials 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- 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
- C08G59/40—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
- C08G59/621—Phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- 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
- C08G59/40—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
-
- 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
- C08G59/68—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 catalysts used
- C08G59/686—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 catalysts used containing nitrogen
-
- 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
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/46—Manufacturing multilayer circuits
Definitions
- the present invention contains a phenol resin which is excellent in fluidity, has an excellent balance of thermal elastic modulus, low moisture absorption property, and dielectric property of a cured product and can be suitably used as a semiconductor encapsulating material, and the phenol resin.
- the present invention relates to a curable resin composition and a cured product thereof.
- Phenol resin is used as a curable resin composition in combination with, for example, an epoxy resin, and is used as an adhesive, a molding material, a paint, a photoresist material, a coloring material, etc., and also has excellent heat resistance and moisture resistance of the obtained cured product. It is widely used in the electrical and electronic fields such as semiconductor encapsulants and insulating materials for printed wiring boards.
- Dicyclopentadienephenol resin and ⁇ -naphthol are esterified with phthalate chloride as a resin that can be suitably used to meet the demands of low moisture absorption, low elastic modulus during heat, and low dielectric loss tangent in the high frequency region.
- phthalate chloride examples thereof include active ester resins (see, for example, Patent Document 1).
- the active ester resin described in Patent Document 1 has improved properties as compared with the case of using a conventional curing agent such as a phenol novolac resin, but does not satisfy the level required in recent years and is highly melted. Due to its viscosity, it is difficult to apply to semiconductor encapsulation materials.
- the problem to be solved by the present invention is that phenol is excellent in fluidity, has an excellent balance of thermal elastic modulus, low hygroscopicity, and dielectric property of the cured product, and can be suitably used for semiconductor encapsulation materials and the like.
- the present invention is to provide a resin, a composition, and a cured product thereof.
- the present invention is a reaction product of a monophenol compound (A) having one hydroxy group on the aromatic ring and an aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring.
- the total peak area of the ester compound represented by the following structural formula (1) and the ketone compound (2) represented by the following structural formula (2) is 70 to 99%.
- the present invention provides a phenol resin, a curable resin composition containing the same, and a cured product thereof.
- R 1 to R 17 are independently hydrogen atoms, alkyl groups having 1 to 4 carbon atoms, or alkoxy groups having 1 to 4 carbon atoms.
- a phenol resin having a low viscosity and excellent fluidity, an excellent balance of thermal elastic modulus, low hygroscopicity, and dielectric properties of a cured product and which can be suitably used as a semiconductor encapsulating material, curable. It is possible to provide a resin composition, a cured product having the above-mentioned performance, a semiconductor encapsulating material, a semiconductor device, a prepreg, a circuit board, a build-up film, a build-up board, a fiber-reinforced composite material, and a fiber-reinforced molded product.
- 6 is a GPC chart of the phenol resin obtained in Example 1.
- 13 C-NMR spectrum of the phenol resin obtained in Example 1. 6 is an MS spectrum of the phenol resin obtained in Example 1.
- 6 is a GPC chart of the phenol resin obtained in Example 2.
- 3 is a 13 C-NMR spectrum of the phenol resin obtained in Example 2.
- 6 is an MS spectrum of the phenol resin obtained in Example 2.
- 6 is a GPC chart of the phenol resin obtained in Example 3.
- 13 C-NMR spectrum of the phenol resin obtained in Example 3. 6 is an MS spectrum of the phenol resin obtained in Example 3. It is a GPC chart of the phenol resin obtained in Example 4.
- 13 C-NMR spectrum of the phenol resin obtained in Example 4. 6 is an MS spectrum of the phenol resin obtained in Example 4.
- 6 is a GPC chart of the phenol resin obtained in Example 5.
- 6 is a 13 C-NMR spectrum of the phenol resin obtained in Example 5.
- 6 is an MS spectrum of the phenol resin obtained in Example 5.
- 6 is a GPC chart of the phenol resin obtained in Example 6.
- 6 is a 13 C-NMR spectrum of the phenol resin obtained in Example 6.
- 6 is an MS spectrum of the phenol resin obtained in Example 6.
- 6 is a GPC chart of the phenol resin obtained in Example 7. It is a 13 C-NMR spectrum of the phenol resin obtained in Example 7.
- 6 is an MS spectrum of the phenol resin obtained in Example 7.
- 6 is a GPC chart of the phenol resin obtained in Example 8.
- 13 C-NMR spectrum of the phenol resin obtained in Example 8. 6 is an MS spectrum of the phenol resin obtained in Example 8.
- the phenolic resin of the present invention is a reaction product of a monophenol compound (A) having one hydroxy group on the aromatic ring and an aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring.
- the total peak area of the ester compound represented by the following structural formula (1) and the ketone compound (2) represented by the following structural formula (2) in the GPC measurement is 70 to 99%. And.
- R 1 to R 17 are independently hydrogen atoms, alkyl groups having 1 to 4 carbon atoms, or alkoxy groups having 1 to 4 carbon atoms.
- R 1 to R 17 in the phenol resin are independently hydrogen atoms, alkyl groups having 1 to 4 carbon atoms or alkoxy groups having 1 to 4 carbon atoms, and in particular, hydrogen atoms and 1 to 2 carbon atoms. It is preferably an alkyl group, preferably a hydrogen atom or a methyl group.
- a monophenol compound (A) having one hydroxy group on the aromatic ring and an aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring are used as raw materials.
- the hydroxy group in the monophenol compound (A) and the carboxy group in the aromatic carboxylic acid (B) are esterified and form a ketone.
- the resin since the resin contains a certain amount of an ester compound in which two aromatic rings are linked and a ketone compound, the molecular weight is low and crystallization is unlikely to occur, so that it is easy to handle and a hydroxy group.
- the ester group which is generally considered to have a slow curing reaction, has a fast-curing property, and can be suitably used as a curable composition.
- the total of these is 70% or more in terms of area% in GPC measurement, the balance between fluidity and curability as a resin is good, and when it is 99% or less, the melting point temperature of the crystal is low. Good handling.
- the ratio of the ester group to the ketone group in the phenol resin is in the range of 1: 0.01 to 1: 0.20 as measured by 13 C-NMR, the hygroscopicity is low and the curability is more excellent. ..
- the curing reaction easily proceeds even if a relatively mild catalyst such as triphenylphosphine is used as the curing catalyst, and it is affected by the curing catalyst remaining in the obtained cured product. It also has the characteristic of being difficult.
- the ester group: ketone group is in the range of 1: 0.01 to 1: 0.15.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) in the present invention can be determined by GPC measurement under the following conditions. it can.
- the ratio of the ester group to the ketone group in the phenol resin in the present invention is the sum of the surface integral values of the peaks between 147 and 154 ppm and the surface integral values of the peaks between 191 and 205 ppm in the following 13 C-NMR measurement. It is calculated as the ratio of the total values.
- the viscosity of the phenolic resin of the present invention is preferably in the range of 0.01 to 5 dPa ⁇ s at 150 ° C. from the viewpoint that it can be suitably used as a semiconductor encapsulant. Further, the melting point obtained when measured at a heating rate of 10 ° C./min using a DSC measuring device is preferably in the range of 30 to 180 ° C.
- the phenolic resin of the present invention comprises a monophenol compound (A) having one hydroxy group on the aromatic ring and an aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring. It is a reactant of.
- the monophenol compound (A) having one hydroxy group on the aromatic ring has an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms as a substituent on the aromatic ring. You may. Among these, from the viewpoint of easy availability of raw materials and better curability of the obtained phenol resin, those having a hydrogen atom or an alkyl group having 1 to 2 carbon atoms as a substituent are preferable, and phenol is particularly preferable. , Cresol or xylenol is preferred. These monophenol compounds (A) may be used alone or in combination of two or more.
- aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms is substituted on the aromatic ring. It may have as a group.
- those having a hydrogen atom or an alkyl group having 1 to 2 carbon atoms as a substituent are preferable, particularly p. -Hydroxybenzoic acid, salicylic acid, and m-hydroxybenzoic acid are preferable.
- aromatic carboxylic acids (B) may be used alone or in combination of two or more.
- phenol compounds and aromatic carboxylic acids may be used in combination as long as the effects of the present invention are not impaired.
- examples of other phenolic compounds include dihydric phenols and trivalent phenols
- examples of other aromatic carboxylic acids include aromatic dicarboxylic acids, their anhydrides, and salicylic acids having an ester structure. Examples include methyl.
- the reaction between the monophenol compound (A) having one hydroxy group on the aromatic ring and the aromatic carboxylic acid (B) having a hydroxy group and a carboxy group on the aromatic ring in the present invention is carried out under an acid catalyst.
- an acid catalyst can be carried out.
- organic or inorganic acids such as sulfuric acid, p-toluenesulfonic acid and oxalic acid, Friedel-Crafts type catalysts such as ferric chloride, zinc chloride and ferric chloride can be used. These may be mentioned alone or in combination of two or more.
- p-toluenesulfonic acid from the viewpoint of reactivity.
- the amount of these acid catalysts used varies depending on the type of catalyst, but is in the range of 0.0005 to 5% by mass with respect to the total mass of the monophenol compound (A) and the aromatic carboxylic acid (B). Is preferable.
- the ratio of the monophenol compound (A) to the aromatic carboxylic acid (B) can be appropriately adjusted according to the physical properties of the target resin, etc., but it is more excellent in fluidity and is cured as described later.
- it is preferably used in the range of 0.95: 1 to 8: 1, and more preferably in the range of 0.97: 1 to 6: 1.
- this reaction can be carried out in the presence of a solvent or in the absence of a solvent.
- a solvent for example, water, toluene, xylene, methanol, ethanol, propanol, ethyl lactate, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1, 5-Pentanediol, 1,6-Hexanediol, 1,7-Heptanediol, 1,8-Octanediol, 1,9-Nonanediol, Trimethylene glycol, Diethylene glycol, Polyethylene glycol, Glycerin, 2-ethoxyethanol, Ethylene Glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monopentyl ether, ethylene glycol dimethyl
- Each of these solvents may be used alone or as a mixed solvent of two or more kinds.
- the amount of the solvent used is usually 10 to 300% by mass, preferably 15 to 250% by mass, based on the total mass of the monophenol compound (A) and the aromatic carboxylic acid (B).
- the reaction temperature is usually 40 to 150 ° C., and the reaction time is usually 1 to 24 hours.
- the acid catalyst is removed by neutralization, washing with water, etc., and then the solvent and unreacted raw materials used as necessary are removed under heating and reduced pressure. If necessary, purification such as reprecipitation can be performed.
- the solvent that can be used for reprecipitation include toluene, methyl ethyl ketone, acetone, methyl isobutyl ketone, n-hexane, methanol, ethanol and the like, but the solvent is not limited thereto, and various solvents may be mixed. For reprecipitation, a usual method of heating these solvents, dissolving the reaction mixture, and then cooling and filtering can be applied.
- the phenol resin of the present invention can be made into a curable resin composition by using another compound having a functional group that reacts with a hydroxyl group in combination.
- the curable resin composition can be suitably used for various electric / electronic member applications such as adhesives, paints, photoresists, printed wiring boards, and semiconductor encapsulant materials.
- Other compounds having a functional group that reacts with the hydroxyl group used in the present invention include, for example, a melamine compound, a guanamine compound, and a glycol uryl substituted with at least one group selected from a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
- examples thereof include compounds containing double bonds such as compounds, urea compounds, resole resins, epoxy resins, isocyanate compounds, azide compounds and alkenyl ether groups, acid anhydrides and oxazoline compounds.
- the melamine compound is, for example, a compound in which 1 to 6 methylol groups of hexamethylol melamine, hexamethoxymethyl melamine, and hexamethylol melamine are methoxymethylated, hexamethoxyethyl melamine, hexaacyloxymethyl melamine, and methylol of hexamethylol melamine. Examples thereof include compounds in which 1 to 6 groups are asyloxymethylated.
- the guanamine compound is, for example, a compound in which 1 to 4 methylol groups of tetramethylol guanamine, tetramethoxymethyl guanamine, tetramethoxymethylbenzoguanamine, and tetramethylol guanamine are methoxymethylated, tetramethoxyethyl guanamine, tetraacyloxyguanamine, and tetra. Examples thereof include compounds in which 1 to 4 methylol groups of methoxyl guanamine are asyloxymethylated.
- the glycol uryl compound is, for example, 1,3,4,6-tetrakis (methoxymethyl) glycol uryl, 1,3,4,6-tetrakis (butoxymethyl) glycol uryl, 1,3,4,6-tetrakis ( Hydroxymethyl) glycol uryl and the like can be mentioned.
- urea compound examples include 1,3-bis (hydroxymethyl) urea, 1,1,3,3-tetrakis (butoxymethyl) urea and 1,1,3,3-tetrakis (methoxymethyl) urea. Be done.
- the resole resin is, for example, an alkaline phenol, an alkylphenol such as cresol or xylenol, a phenylphenol, a resorcinol, a biphenyl, a bisphenol such as bisphenol A or bisphenol F, a phenolic hydroxyl group-containing compound such as naphthol or dihydroxynaphthalene, and an aldehyde compound.
- alkaline phenol an alkylphenol such as cresol or xylenol
- a phenylphenol a resorcinol
- a biphenyl a bisphenol such as bisphenol A or bisphenol F
- a phenolic hydroxyl group-containing compound such as naphthol or dihydroxynaphthalene
- aldehyde compound examples thereof include a polymer obtained by reacting under catalytic conditions.
- epoxy resin examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, biphenyl type epoxy resin, tetramethylbiphenyl type epoxy resin, polyhydroxynaphthalene type epoxy resin, phenol novolac type epoxy resin, and cresol novolac type epoxy resin.
- Triphenylmethane type epoxy resin Triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, dicyclopentadiene-phenol addition reaction type epoxy resin, phenol aralkyl type epoxy resin, naphthol novolac type epoxy resin, diglycidyloxynaphthalene, naphthol aralkyl type epoxy resin, naphthol- Phenolic co-condensed novolac type epoxy resin, naphthol-cresol co-condensed novolak type epoxy resin, aromatic hydrocarbon formaldehyde resin modified phenol resin type epoxy resin, biphenyl modified novolac type epoxy resin, 1,1-bis (2,7-diglycidyl) Oxy-1-naphthyl) alkane, naphthylene ether type epoxy resin, triphenylmethane type epoxy resin, phosphorus atom-containing epoxy resin, polyglycidyl ether of cocondensate of phenolic hydroxyl group-containing compound and al
- epoxy resins tetramethylbiphenol type epoxy resin, biphenylaralkyl type epoxy resin, polyhydroxynaphthalene type epoxy resin, and novolac type epoxy resin can be used in that a cured product having particularly excellent flame retardancy can be obtained.
- a dicyclopentadiene-phenol addition reaction type epoxy resin is preferable, and a cured product having excellent dielectric properties can be obtained.
- isocyanate compound examples include tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, cyclohexane diisocyanate and the like.
- azide compound examples include 1,1'-biphenyl-4,4'-bis azide, 4,4'-methylidene azide, 4,4'-oxybis azide and the like.
- Compounds containing a double bond such as the alkenyl ether group include, for example, ethylene glycol divinyl ether, triethylene glycol divinyl ether, 1,2-propanediol divinyl ether, 1,4-butanediol divinyl ether, and tetramethylene glycol divinyl ether.
- the acid anhydrides include, for example, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, 3,3', 4,4'-benzophenone tetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, 4,4.
- Aromatic acid anhydrides such as'-(isopropyridene) diphthalic anhydride, 4,4'-(hexafluoroisopropylidene) diphthalic anhydride; tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride , Alicyclic carboxylic acid anhydrides such as methylhexahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride dodecenylsuccinic anhydride, and trialkyltetrahydrophthalic anhydride.
- an epoxy resin is particularly preferable because it is a curable composition having excellent curability and heat resistance in the cured product and having good dielectric properties.
- a curing agent for epoxy resin may be blended.
- curing agent examples include various known curing agents for epoxy resins such as amine compounds, amide compounds, acid anhydride compounds, and phenol compounds.
- diaminodiphenylmethane as amine compound diethylenetriamine, triethylenetetramine, diaminodiphenyl sulfone, isophoronediamine, imidazo - Le, BF 3 - amine complex, guanidine derivatives and the like
- amide compounds include dicyandiamide , Polyamide resin synthesized by a dimer of linolenic acid and ethylenediamine, and the like.
- acid anhydride compounds include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, and methylhexahydro.
- acid anhydride compounds include phthalic anhydride.
- phenolic compounds include phenol novolac resin, cresol novolac resin, aromatic hydrocarbon formaldehyde resin-modified phenol resin, dicyclopentadienephenol-added resin, phenol aralkyl resin (Zyroc resin), naphthol aralkyl resin, and triphenylol methane resin.
- a curing catalyst can be used in combination.
- the phenol resin of the present invention has excellent curability, a cured product can be obtained without using a strong base catalyst such as dimethylaminopyridine, which is conventionally used when an active ester is used as a curing agent.
- a phosphorus compound such as phenylphosphine or a nitrogen-containing compound, the influence of the residual catalyst in the cured product can be suppressed.
- curable resin composition of the present invention may be used in combination with other thermosetting resins.
- thermosetting resins examples include cyanate ester resins, resins having a benzoxazine structure, maleimide compounds, active ester resins, vinylbenzyl compounds, acrylic compounds, copolymers of styrene and maleic acid anhydride, and the like. ..
- the amount used is not particularly limited as long as the effect of the present invention is not impaired, but is in the range of 1 to 50 parts by mass out of 100 parts by mass of the curable resin composition. It is preferable to have.
- cyanate ester resin examples include bisphenol A type cyanate ester resin, bisphenol F type cyanate ester resin, bisphenol E type cyanate ester resin, bisphenol S type cyanate ester resin, bisphenol sulfide type cyanate ester resin, and phenylene ether type cyanate ester resin.
- Naftyrene ether type cyanate ester resin Naftyrene ether type cyanate ester resin, biphenyl type cyanate ester resin, tetramethylbiphenyl type cyanate ester resin, polyhydroxynaphthalene type cyanate ester resin, phenol novolac type cyanate ester resin, cresol novolac type cyanate ester resin, triphenylmethane type cyanate Ester resin, tetraphenylethane type cyanate ester resin, dicyclopentadiene-phenol addition reaction type cyanate ester resin, phenol aralkyl type cyanate ester resin, naphthol novolac type cyanate ester resin, naphthol aralkyl type cyanate ester resin, naphthol-phenol co-condensed novolak
- Examples thereof include type cyanate ester resin, naphthol-cresol co-condensed novolak type cyanate ester resin, aromatic hydrocarbon formal
- cyanate ester resins bisphenol A type cyanate ester resin, bisphenol F type cyanate ester resin, bisphenol E type cyanate ester resin, and polyhydroxynaphthalene type cyanate ester resin can be obtained as a cured product having particularly excellent heat resistance.
- Naftylene ether type cyanate ester resin and novolak type cyanate ester resin are preferably used, and dicyclopentadiene-phenol addition reaction type cyanate ester resin is preferable in that a cured product having excellent dielectric properties can be obtained.
- the resin having a benzoxazine structure is not particularly limited, but for example, a reaction product of bisphenol F, formalin and aniline (Fa type benzoxazine resin) or a reaction product of diaminodiphenylmethane, formalin and phenol (P-).
- D-type benzoxazine resin D-type benzoxazine resin
- reaction product of bisphenol A, formalin and aniline reaction product of dihydroxydiphenyl ether, formalin and aniline
- reaction product of diaminodiphenyl ether, formalin and phenol dicyclopentadiene-phenol addition type resin and formalin
- aniline reaction products phenolphthalein, formalin and aniline reaction products, diphenylsulfide, formalin and aniline reaction products, and the like.
- Each of these may be used alone, or two or more types may be used in combination.
- maleimide compound examples include various compounds represented by any of the following structural formulas (i) to (iii).
- R is an organic group having an m valence
- ⁇ and ⁇ are any of a hydrogen atom, a halogen atom, an alkyl group and an aryl group, respectively, and s is an integer of 1 or more.
- R is any of a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group, and an alkoxy group
- s is an integer of 1 to 3
- t is an average of 0 to 10 in repeating units. .
- R is any of a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a halogen atom, a hydroxyl group, and an alkoxy group
- s is an integer of 1 to 3
- t is an average of 0 to 10 in repeating units. .
- the active ester resin is not particularly limited, but generally contains an ester group having high reactive activity such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds in one molecule.
- a compound having two or more is preferably used.
- the active ester resin is preferably obtained by a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound.
- an active ester resin obtained from a carboxylic acid compound or a halide thereof and a hydroxy compound is preferable, and an active ester resin obtained from a carboxylic acid compound or a halide thereof and a phenol compound and / or a naphthol compound is preferable.
- the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid and the like, or halides thereof.
- phenol compound or naphthol compound examples include hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, dihydroxydiphenyl ether, phenol phthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m.
- -Cresol p-cresol, catechol, ⁇ -naphthol, ⁇ -naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenol, trihydroxybenzophenone, tetrahydroxybenzophenone, fluoroglusin , Benzintriol, dicyclopentadiene-phenol-added resin and the like.
- the active ester resin examples include an active ester resin containing a dicyclopentadiene-phenol addition structure, an active ester resin containing a naphthalene structure, an active ester resin which is an acetylated product of phenol novolac, and an activity which is a benzoyl product of phenol novolac.
- Ester resins and the like are preferable, and among them, an active ester resin containing a dicyclopentadiene-phenol addition structure and an active ester resin containing a naphthalene structure are more preferable in that they are excellent in improving peel strength.
- Specific examples of the active ester resin containing a dicyclopentadiene-phenol addition structure include compounds represented by the following general formula (iv).
- R is a phenyl group or a naphthyl group
- u represents 0 or 1
- n is an average of 0.05 to 2.5 in repeating units.
- R is preferably a naphthyl group
- u is preferably 0, and n is preferably 0.25 to 1.5. ..
- novolak resins other than the phenol resin of the present invention, addition polymerized resins of alicyclic diene compounds such as dicyclopentadiene and phenol compounds, and modified novolak resins of phenolic hydroxyl group-containing compounds and alkoxy group-containing aromatic compounds.
- Phenol aralkyl resin Zyroc resin
- naphthol aralkyl resin trimethylolmethane resin
- tetraphenylol ethane resin biphenyl-modified phenol resin
- biphenyl-modified naphthol resin aminotriazine-modified phenol resin
- various vinyl polymers in combination May be good.
- the various novolak resins are acid catalysts of phenol, phenylphenol, resorcinol, biphenyl, bisphenol such as bisphenol A and bisphenol F, phenolic hydroxyl group-containing compounds such as naphthol and dihydroxynaphthalene, and aldehyde compounds.
- acid catalysts of phenol, phenylphenol, resorcinol, biphenyl, bisphenol such as bisphenol A and bisphenol F, phenolic hydroxyl group-containing compounds such as naphthol and dihydroxynaphthalene, and aldehyde compounds examples thereof include a polymer obtained by reacting under conditions.
- the various vinyl polymers include polyhydroxystyrene, polystyrene, polyvinylnaphthalene, polyvinylanthracene, polyvinylcarbazole, polyinden, polyacenaftylene, polynorbornene, polycyclodecene, polytetracyclododecene, polynortricyclene, and poly (polynortricyclene, poly). Examples thereof include homopolymers of vinyl compounds such as meth) acrylates and copolymers thereof.
- the blending ratio of the phenol resin of the present invention and the other resin can be arbitrarily set according to the intended use, but the thermal elasticity and the dielectric property of the cured product exhibited by the present invention can be set arbitrarily. It is preferable that the ratio of the other resin to 100 parts by mass is 0.5 to 100 parts by mass with respect to 100 parts by mass of the phenol resin of the present invention, because the balance effect such as the above is more remarkable.
- a non-halogen flame retardant substantially containing no halogen atom may be blended.
- non-halogen flame retardant examples include phosphorus-based flame retardants, nitrogen-based flame retardants, silicone-based flame retardants, inorganic flame retardants, organic metal salt-based flame retardants, and the like, and their use is also restricted. They may be used alone, a plurality of flame retardants of the same system may be used, or different flame retardants may be used in combination.
- the phosphorus-based flame retardant can be either inorganic or organic.
- the inorganic compound include ammonium phosphates such as red phosphorus, monoammonium phosphate, diammonium phosphate, triammonium phosphate and ammonium polyphosphate, and inorganic nitrogen-containing phosphorus compounds such as phosphate amide. ..
- the red phosphorus is preferably surface-treated for the purpose of preventing hydrolysis and the like, and examples of the surface treatment method include (i) magnesium hydroxide, aluminum hydroxide, zinc hydroxide and water.
- the organic phosphorus compounds include, for example, general-purpose organic phosphorus compounds such as phosphoric acid ester compounds, phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphoran compounds, and organic nitrogen-containing phosphorus compounds, as well as 9,10-dihydro.
- general-purpose organic phosphorus compounds such as phosphoric acid ester compounds, phosphonic acid compounds, phosphinic acid compounds, phosphine oxide compounds, phosphoran compounds, and organic nitrogen-containing phosphorus compounds, as well as 9,10-dihydro.
- the blending amount of these phosphorus-based flame retardants is appropriately selected depending on the type of the phosphorus-based flame retardant, other components of the resin composition, and the desired degree of flame retardancy.
- a non-halogen flame retardant When red phosphorus is used as a non-halogen flame retardant, it is blended in the range of 0.1 parts by mass to 2.0 parts by mass in 100 parts by mass of the resin composition containing all of the fillers and other additives.
- an organic phosphorus compound when an organic phosphorus compound is used, it is preferably blended in the range of 0.1 parts by mass to 10.0 parts by mass, and blended in the range of 0.5 parts by mass to 6.0 parts by mass. It is more preferable to do so.
- hydrotalcite magnesium hydroxide, boron compound, zirconium oxide, black dye, calcium carbonate, zeolite, zinc molybdate, activated charcoal, etc. may be used in combination with the phosphorus-based flame retardant.
- hydrotalcite magnesium hydroxide
- boron compound boron compound
- zirconium oxide black dye
- calcium carbonate calcium carbonate
- zeolite zeolite
- zinc molybdate activated charcoal, etc.
- nitrogen-based flame retardant examples include triazine compounds, cyanuric acid compounds, isocyanuric acid compounds, and phenothiazine, and triazine compounds, cyanuric acid compounds, and isocyanuric acid compounds are preferable.
- the triazine compound includes, for example, melamine, acetoguanamine, benzoguanamine, melon, melam, succinoguanamine, ethylenedimelamine, polyphosphate melamine, triguanamine and the like, and for example, (1) guanyl melamine sulfate, melem sulfate, melam sulfate.
- Aminotriazine sulfate compounds such as (2) Phenols such as phenol, cresol, xylenol, butylphenol, nonylphenol and melamines such as melamine, benzoguanamine, acetguanamine, formguanamine and formaldehyde, (3) the above. Examples thereof include a mixture of the cocondensate of (2) and phenolic resins such as phenol formaldehyde condensate, and (4) the above (2) and (3) further modified with tung oil, isomerized melamine oil and the like.
- cyanuric acid compound examples include cyanuric acid and melamine cyanuric acid.
- the blending amount of the nitrogen-based flame retardant is appropriately selected depending on the type of the nitrogen-based flame retardant, other components of the resin composition, and the desired degree of flame retardancy.
- a non-halogen flame retardant It is preferable to mix in the range of 0.05 to 10 parts by mass, and in the range of 0.1 parts by mass to 5 parts by mass, out of 100 parts by mass of the resin composition containing all of the other fillers and additives. It is more preferable to do so.
- a metal hydroxide, a molybdenum compound, or the like may be used in combination.
- the silicone-based flame retardant can be used without particular limitation as long as it is an organic compound containing a silicon atom, and examples thereof include silicone oil, silicone rubber, and silicone resin.
- the blending amount of the silicone-based flame retardant is appropriately selected depending on the type of the silicone-based flame retardant, other components of the resin composition, and the desired degree of flame retardancy.
- a non-halogen flame retardant It is preferable to blend in the range of 0.05 to 20 parts by mass in 100 parts by mass of the resin composition containing all of the other fillers and additives.
- a molybdenum compound, alumina or the like may be used in combination.
- inorganic flame retardant examples include metal hydroxides, metal oxides, metal carbonate compounds, metal powders, boron compounds, and low melting point glass.
- metal hydroxide examples include aluminum hydroxide, magnesium hydroxide, dolomite, hydrotalcite, calcium hydroxide, barium hydroxide, zirconium hydride and the like.
- the metal oxides include, for example, zinc molybdenum, molybdenum trioxide, zinc tinate, tin oxide, aluminum oxide, iron oxide, titanium oxide, manganese oxide, zirconium oxide, zinc oxide, molybdenum oxide, cobalt oxide, and bismuth oxide. Examples thereof include chromium oxide, nickel oxide, copper oxide, and tungsten oxide.
- metal carbonate compound examples include zinc carbonate, magnesium carbonate, calcium carbonate, barium carbonate, basic magnesium carbonate, aluminum carbonate, iron carbonate, cobalt carbonate, titanium carbonate and the like.
- metal powder examples include aluminum, iron, titanium, manganese, zinc, molybdenum, cobalt, bismuth, chromium, nickel, copper, tungsten, tin and the like.
- Examples of the boron compound include zinc borate, zinc metaborate, barium metaborate, boric acid, and borax.
- the low melting point glass includes, for example, Shipley (Boxy Brown Co., Ltd.), hydrated glass SiO 2 -MgO-H 2 O, PbO-B 2 O 3 system, ZnO-P 2 O 5- MgO system, P 2 O 5 -B 2 O 3- PbO-MgO system, P-Sn-OF system, PbO-V 2 O 5- TeO 2 system, Al 2 O 3- H 2 O system, lead borosilicate glassy compounds, etc. Can be mentioned.
- the blending amount of the inorganic flame retardant is appropriately selected depending on the type of the inorganic flame retardant, other components of the resin composition, and the desired degree of flame retardancy.
- a non-halogen flame retardant It is preferable to blend in the range of 0.05 parts by mass to 20 parts by mass, and in the range of 0.5 parts by mass to 15 parts by mass, out of 100 parts by mass of the resin composition containing all of the other fillers and additives. It is more preferable to mix with.
- the organometallic salt-based flame retardant includes, for example, ferrocene, an acetylacetonate metal complex, an organometallic carbonyl compound, an organocobalt salt compound, an organosulfonic acid metal salt, a metal atom and an aromatic compound or a heterocyclic compound in an ionic bond or arrangement. Examples thereof include position-bonded compounds.
- the blending amount of the organic metal salt-based flame retardant is appropriately selected depending on the type of the organic metal salt-based flame retardant, other components of the resin composition, and the desired degree of flame retardancy. It is preferable to blend in the range of 0.005 parts by mass to 10 parts by mass in 100 parts by mass of the resin composition containing all of the halogen-based flame retardant and other fillers and additives.
- the curable resin composition of the present invention can be blended with an inorganic filler as needed.
- the inorganic filler include fused silica, crystalline silica, alumina, silicon nitride, aluminum hydroxide and the like.
- fused silica When the blending amount of the inorganic filler is particularly large, it is preferable to use fused silica.
- the molten silica can be used in either a crushed form or a spherical shape, but in order to increase the blending amount of the molten silica and suppress an increase in the melt viscosity of the molding material, it is preferable to mainly use a spherical one.
- the filling rate is preferably high in consideration of flame retardancy, and is particularly preferably 20% by mass or more with respect to the total mass of the curable resin composition.
- a conductive filler such as silver powder or copper powder can be used.
- various compounding agents such as a silane coupling agent, a mold release agent, a pigment, and an emulsifier can be added to the curable resin composition of the present invention, if necessary.
- the curable resin composition of the present invention shall be applied to semiconductor encapsulant materials, semiconductor devices, prepregs, printed circuit boards, build-up substrates, build-up films, fiber-reinforced composite materials, fiber-reinforced resin molded products, conductive pastes, and the like. Can be done.
- the curable resin composition and a compounding agent such as an inorganic filler are used in an extruder or a feeder as necessary.
- a method of sufficiently melting and mixing until uniform using a roll or the like can be mentioned.
- fused silica is usually used as the inorganic filler, but when used as a high thermal conductivity semiconductor encapsulant for power transistors and power ICs, crystalline silica, alumina, and silicon nitride having higher thermal conductivity than fused silica are used.
- high-filling silicon or the like or use molten silica, crystalline silica, alumina, silicon nitride, or the like. It is preferable to use an inorganic filler in the range of 30 parts by mass to 95 parts by mass per 100 parts by mass of the curable resin composition, and among them, improvement of flame retardancy, moisture resistance and solder crack resistance, wire In order to reduce the coefficient of expansion, 70 parts by mass or more is more preferable, and 80 parts by mass or more is further preferable.
- the semiconductor encapsulant material is cast or molded using a transfer molding machine, an injection molding machine, or the like, and further at 50 to 200 ° C. 2 Examples include a method of heating for up to 10 hours.
- a curable resin composition obtained by blending an organic solvent to form a varnish is used as a reinforcing base material (paper, glass cloth, glass non-woven fabric, aramid paper, aramid cloth). , Glass mat, glass roving cloth, etc.), and then heated at a heating temperature according to the type of solvent used, preferably 50 to 170 ° C., to obtain the method.
- the mass ratio of the resin composition and the reinforcing base material used at this time is not particularly limited, but it is usually preferable to prepare the resin content in the prepreg to be 20% by mass to 60% by mass.
- organic solvent used here examples include methyl ethyl ketone, acetone, dimethylformamide, methyl isobutyl ketone, methoxypropanol, cyclohexanone, methyl cellosolve, ethyl diglycol acetate, propylene glycol monomethyl ether acetate, and the like. It can be appropriately selected depending on the application, but for example, when further producing a printed circuit board from prepylene as described below, it is preferable to use a polar solvent having a boiling point of 160 ° C. or lower, such as methyl ethyl ketone, acetone, or dimethylformamide. , It is preferable to use the non-volatile content at a ratio of 40% by mass to 80% by mass.
- the prepregs are laminated by a conventional method, copper foils are appropriately laminated, and the pressure is 170 to 300 ° C. under a pressure of 1 to 10 MPa. Examples thereof include a method of heat-bonding for 10 minutes to 3 hours.
- step 1 first, the curable resin composition in which rubber, a filler and the like are appropriately mixed is applied to a circuit board on which a circuit is formed by a spray coating method, a curtain coating method or the like, and then cured.
- step 2 if necessary, a circuit board coated with the curable resin composition is drilled with a predetermined through-hole portion or the like, treated with a roughening agent, and the surface thereof is washed with hot water. Unevenness is formed on the substrate, and a metal such as copper is plated.
- step 3 the operations of steps 1 and 2 are sequentially repeated as desired, and the resin insulating layer and the conductor layer having a predetermined circuit pattern are alternately built up to form a build-up substrate.
- the through-hole portion may be drilled after the resin insulating layer of the outermost layer is formed.
- the build-up substrate of the present invention is roughened by heat-pressing a resin-containing copper foil obtained by semi-curing the resin composition on a copper foil onto a wiring board on which a circuit is formed at 170 to 300 ° C. It is also possible to produce a build-up substrate by omitting the steps of forming a chemical surface and plating.
- a curable resin composition is applied on a support film, dried, and a resin composition layer is placed on the support film.
- a method of forming There is a method of forming.
- the film is softened under the temperature conditions of lamination (usually 70 ° C. to 140 ° C.) in the vacuum laminating method, and is applied to the circuit board at the same time as laminating the circuit board. It is important to exhibit fluidity (resin flow) capable of filling the existing via hole or through hole with resin, and it is preferable to blend each of the above components so as to exhibit such characteristics.
- the diameter of the through hole of the circuit board is usually 0.1 to 0.5 mm, and the depth is usually 0.1 to 1.2 mm, and it is usually preferable to enable resin filling in this range.
- a resin composition varnished by blending an organic solvent is prepared, and then the composition is applied to the surface of the support film (Y) and further heated.
- a method of drying the organic solvent by blowing hot air or the like to form the layer (X) of the resin composition can be mentioned.
- organic solvent used here examples include ketones such as acetone, methyl ethyl ketone and cyclohexanone, acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- ketones such as acetone, methyl ethyl ketone and cyclohexanone
- acetic acid esters such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate and carbitol acetate, cellosolve and butyl carbitol.
- Carbitols, aromatic hydrocarbons such as toluene and xylene, dimethylformamide, dimethylacetamide, N-methylpyrrolidone and the like are preferably used, and the non-volatile
- the thickness of the layer (X) of the resin composition to be formed usually needs to be equal to or greater than the thickness of the conductor layer. Since the thickness of the conductor layer of the circuit board is usually in the range of 5 to 70 ⁇ m, the thickness of the resin composition layer is preferably 10 to 100 ⁇ m.
- the layer (X) of the resin composition in the present invention may be protected by a protective film described later. By protecting with a protective film, it is possible to prevent dust and the like from adhering to the surface of the resin composition layer and scratches.
- the support film and protective film described above include polyolefins such as polyethylene, polypropylene and polyvinyl chloride, polyethylene terephthalate (hereinafter, may be abbreviated as "PET"), polyesters such as polyethylene naphthalate, polycarbonate, polyimide, and further release. Examples include metal foils such as patterns, copper foils, and aluminum foils.
- the support film and the protective film may be subjected to a mold release treatment in addition to the mud treatment and the corona treatment.
- the thickness of the support film is not particularly limited, but is usually 10 to 150 ⁇ m, and is preferably used in the range of 25 to 50 ⁇ m.
- the thickness of the protective film is preferably 1 to 40 ⁇ m.
- the support film (Y) described above is peeled off after being laminated on a circuit board or after forming an insulating layer by heat curing. If the support film (Y) is peeled off after the resin composition layer constituting the build-up film is heat-cured, it is possible to prevent the adhesion of dust and the like in the curing step. When peeling off after curing, the support film is usually subjected to a mold release treatment in advance.
- a multilayer printed circuit board can be manufactured from the build-up film obtained as described above.
- the layers (X) of the resin composition are peeled off, and then one side or both sides of the circuit board are brought into direct contact with the layer (X) of the resin composition.
- the laminating method may be a batch method or a continuous method using a roll. If necessary, the build-up film and the circuit board may be preheated if necessary before laminating.
- the crimping temperature (lamination temperature) is preferably 70 to 140 ° C., and the crimping pressure is 1 to 11 kgf / cm 2 (9.8 ⁇ 10 4 to 107.9 ⁇ 10 4 N / m 2 ). It is preferable to laminate under a reduced air pressure of 20 mmHg (26.7 hPa) or less.
- Fiber-reinforced composite material As a method of obtaining a fiber-reinforced composite material (a sheet-like intermediate material in which a resin is impregnated in a reinforcing fiber) from the resin composition of the present invention, each component constituting the resin composition is uniformly mixed and varnished. Then, after impregnating the reinforcing base material made of reinforcing fibers with the reinforcing base material, a polymerization reaction is carried out to produce the material.
- a fiber-reinforced composite material a sheet-like intermediate material in which a resin is impregnated in a reinforcing fiber
- the curing temperature at the time of carrying out such a polymerization reaction is preferably in the temperature range of 50 to 250 ° C., in particular, after curing at 50 to 100 ° C. to obtain a tack-free cured product, further , It is preferable to treat at a temperature condition of 120 to 200 ° C.
- the reinforcing fiber may be a twisted yarn, an untwisted yarn, or an untwisted yarn, but the untwisted yarn or the untwisted yarn is preferable because both the moldability and the mechanical strength of the fiber-reinforced plastic member are compatible.
- the form of the reinforcing fiber one in which the fiber directions are aligned in one direction or a woven fabric can be used.
- plain weaves, satin weaves, and the like can be freely selected according to the part to be used and the intended use. Specific examples thereof include carbon fiber, glass fiber, aramid fiber, boron fiber, alumina fiber, and silicon carbide fiber because of their excellent mechanical strength and durability, and two or more of these can be used in combination.
- carbon fibers are particularly preferable from the viewpoint of improving the strength of the molded product, and various carbon fibers such as polyacrylonitrile-based, pitch-based, and rayon-based can be used.
- various carbon fibers such as polyacrylonitrile-based, pitch-based, and rayon-based can be used.
- polyacrylonitrile-based ones which can easily obtain high-strength carbon fibers, are preferable.
- the amount of the reinforcing fiber used when impregnating the reinforcing base material made of the reinforcing fiber with the varnish to obtain the fiber-reinforced composite material is such that the volume content of the reinforcing fiber in the fiber-reinforced composite material is 40% to 85%.
- the amount is preferably in the range of.
- Fiber-reinforced resin molded product As a method of obtaining a fiber-reinforced molded product (molded product in which a sheet-like member impregnated with resin impregnated in reinforcing fibers is cured) from the resin composition of the present invention, a fiber aggregate is laid on a mold and the varnish is applied. Using either the hand lay-up method, spray-up method, or male or female type, in which multiple layers are laminated, the base material made of reinforcing fibers is impregnated with varnish and stacked to form, and pressure is applied to the molded product.
- Vacuum bag method in which a flexible mold that can be used is covered and airtightly sealed is vacuum (decompressed) molded, SMC press method in which a sheet of varnish containing reinforcing fibers is previously compression-molded with a mold, and fibers are laid out.
- Examples thereof include a method of producing a prepreg in which reinforcing fibers are impregnated with the varnish by an RTM method in which the varnish is injected into a mating mold, and baking the prepreg with a large autoclave.
- the fiber-reinforced resin molded product obtained above is a molded product having a reinforcing fiber and a cured product of the resin composition.
- the amount of the reinforcing fiber in the fiber-reinforced molded product is 40 mass. It is preferably in the range of% to 70% by mass, and particularly preferably in the range of 50% by mass to 70% by mass from the viewpoint of strength.
- Conductive Paste As a method for obtaining a conductive paste from the resin composition of the present invention, for example, a method of dispersing fine conductive particles in the curable resin composition can be mentioned.
- the conductive paste can be a paste resin composition for circuit connection or an anisotropic conductive adhesive depending on the type of fine conductive particles used.
- ⁇ GPC measurement conditions Measuring device: "HLC-8320 GPC” manufactured by Tosoh Corporation, Column: Guard column “HXL-L” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G2000HXL” manufactured by Tosoh Corporation + “TSK-GEL G3000HXL” manufactured by Tosoh Corporation + “TSK-GEL G4000HXL” manufactured by Tosoh Corporation Detector: RI (Differential Refractometer)
- Data processing "GPC Workstation EcoSEC-WorkStation” manufactured by Tosoh Corporation Measurement conditions: Column temperature 40 ° C Developing solvent Tetrahydrofuran Flow velocity 1.0 ml / min Standard: The following monodisperse polystyrene with a known molecular weight was used in accordance with the measurement manual of the above-mentioned "GPC workstation EcoSEC-WorkStation".
- Example 1 565 g (6 mol) of phenol, 207 g (1.5 mol) of p-hydroxybenzoic acid, p-toluenesulfonic acid dihydration while performing nitrogen gas purging on a flask equipped with a thermometer, a fractional tube, a cooling tube, and a stirrer. 7.7 g of the product and 207 g of toluene were charged. The temperature was raised to 140 ° C. while collecting water with a fractional distillation tube, and the mixture was reacted for 12 hours.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 86%, and the monophenol residue was 1.7%. .. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.06.
- Example 2 Phenol resin (2) was obtained in the same manner as in Example 1 except that the phenol was changed to 649 g (6 mol) of orthocresol and the reaction temperature was changed to 150 ° C. The melting point of the obtained phenol resin (2) was 135 ° C.
- the GPC chart of the phenol resin (2) is shown in FIG. 4, the 13 C-NMR chart is shown in FIG. 5, and the MS spectrum is shown in FIG.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 91%, and the monophenol residue was 0.1%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.05.
- Example 3 Phenol resin (3) was obtained in the same manner as in Example 1 except that the phenol was paracresol 649 g (6 mol) and the reaction temperature was changed to 150 ° C. The melting point of the obtained phenol resin (3) was 165 ° C.
- the GPC chart of the phenol resin (3) is shown in FIG. 7, the 13 C-NMR chart is shown in FIG. 8, and the MS spectrum is shown in FIG. From GPC, the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) was 88%, and the monophenol residue was 6.5%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.02.
- Example 4 Phenol resin (4) was obtained in the same manner as in Example 1 except that the phenol was 649 g (6 mol) of metacresol and the reaction temperature was changed to 150 ° C. The melting point of the obtained phenol resin (4) was 130 ° C.
- the GPC chart of the phenol resin (4) is shown in FIG. 10, the 13 C-NMR chart is shown in FIG. 11, and the MS spectrum is shown in FIG. From GPC, the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) was 86%, and the monophenol residue was 6.2%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.10.
- Example 5 Phenol resin (5) was obtained in the same manner as in Example 1 except that the phenol was changed to 733 g (6 mol) of 2,6-xylenol and the reaction temperature was changed to 160 ° C. The melting point of the obtained phenol resin (5) was 176 ° C.
- the GPC chart of the phenol resin (5) is shown in FIG. 13, the 13 C-NMR chart is shown in FIG. 14, and the MS spectrum is shown in FIG.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 93%, and the monophenol residue was 0.2%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.03.
- Example 6 Phenol resin (6) was obtained in the same manner as in Example 1 except that the phenol was changed to 733 g (6 mol) of 2,4-xylenol and the reaction temperature was changed to 160 ° C. The melting point of the obtained phenol resin (6) was 155 ° C.
- the GPC chart of the phenol resin (6) is shown in FIG. 16, the 13 C-NMR chart is shown in FIG. 17, and the MS spectrum is shown in FIG.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 97%, and the monophenol residue was 0.1%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.03.
- Example 7 Phenol in the same manner as in Example 1 except that p-hydroxybenzoic acid was changed to 207 g (1.5 mol) of salicylic acid, p-toluenesulfonic acid dihydrate was changed to 15.4 g, and the reaction temperature was changed to 180 ° C. Resin (7) was obtained. The melting point of the obtained phenol resin (7) was 40 ° C.
- the GPC chart of the phenol resin (7) is shown in FIG. 19, the 13 C-NMR chart is shown in FIG. 20, and the MS spectrum is shown in FIG.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 98%, and the monophenol residue was 0.1%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.01.
- Example 8 Phenol in the same manner as in Example 2 except that p-hydroxybenzoic acid was changed to 207 g (1.5 mol) of salicylic acid, p-toluenesulfonic acid dihydrate was changed to 15.4 g, and the reaction temperature was changed to 180 ° C. Resin (8) was obtained. The melting point of the obtained phenol resin (8) was 83 ° C.
- the GPC chart of the phenol resin (8) is shown in FIG. 22, the 13 C-NMR chart is shown in FIG. 23, and the MS spectrum is shown in FIG. 24.
- the total peak area of the ester compound represented by the structural formula (1) and the ketone compound (2) represented by the structural formula (2) from GPC was 97%, and the monophenol residue was 0.1%. From 13 C-NMR, the ratio of ester group: ketone group was 1: 0.02.
- Examples 9 to 16, Comparative Example 1 A curable resin composition was obtained by blending with the compositions shown in Table 1. This was poured into a mold of 11 cm ⁇ 9 cm ⁇ 2.4 mm, molded by a press at a temperature of 175 ° C. for 1 hour, and then cured at a temperature of 175 ° C. for 5 hours to prepare a cured product. The elastic modulus at heat, the dielectric loss tangent, and the hygroscopicity of the obtained cured product were measured. The results are shown at the bottom of Table 1.
- the raw materials used to prepare the composition are as follows.
- -HE100C-15 Phenylaralkyl type phenol resin, hydroxyl group equivalent: 174 g / eq (manufactured by Air Water Inc.)
- N-655-EXP-S Cresol novolac type epoxy resin, epoxy equivalent 201 g / eq (manufactured by DIC Corporation)
- TPP Triphenylphosphine
- the cured product obtained above was vacuum-dried by heating at 105 ° C. for 2 hours, and then stored in a room at a temperature of 23 ° C. and a humidity of 50% for 24 hours as a test piece.
- the dielectric loss tangent of the test piece at 1 GHz was measured by the cavity resonance method using a “network analyzer E8632C” manufactured by Agilent Technologies, Inc.
- Comparative Example 2 A composition was prepared by melt-kneading at a temperature of 90 ° C. for 5 minutes using two rolls having a composition ratio shown in Table 2. The obtained composition was evaluated for fluidity (spiral flow) and flame retardancy according to the following.
- the curable resin composition was injected into a test mold, and the spiral flow value was measured under the conditions of a temperature of 175 ° C., an injection pressure of 70 kg / cm 2, and 300 seconds.
- the curable resin composition was molded with a transfer molding machine at a sample having a width of 12.7 mm, a length of 127 mm, and a thickness of 1.6 mm at 175 ° C. for 5 minutes, and then cured at 175 ° C. for 5 hours to prepare an evaluation sample. ..
- a combustion test was conducted using the five samples according to the UL-94 test method. * 1: Maximum combustion time (seconds) for one flame contact * 2: Total burning time (seconds) of 5 test pieces
- the raw materials used to prepare the composition are as follows.
- -HE100C-15 Phenylaralkyl type phenol resin, hydroxyl group equivalent: 174 g / eq (manufactured by Air Water Inc.)
- N-655-EXP-S Cresol novolac type epoxy resin, epoxy equivalent 201 g / eq (manufactured by DIC Corporation)
- TPP Triphenylphosphine
- Fused silica Spherical silica "FB-5604" manufactured by Denka Co., Ltd.
- Silane coupling agent ⁇ -glycidoxytriethoxyxisilane "KBM-403" manufactured by Shin-Etsu Chemical Co., Ltd.
- Carnauba wax "PEARL WAX No.1-P” manufactured by Denka Co., Ltd.
Abstract
Description
以下、本発明を詳細に説明する。
本発明のフェノール樹脂は、芳香環上にヒドロキシ基を1つ有するモノフェノール化合物(A)と、芳香環上にヒドロキシ基とカルボキシ基とを有する芳香族カルボン酸(B)との反応物であり、GPC測定において下記構造式(1)で表されるエステル化合物と、下記構造式(2)で表されるケトン化合物(2)との合計のピーク面積が、70~99%であることを特徴とする。
<GPC測定条件>
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 G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G4000HXL」
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ワークステーション EcoSEC―WorkStation」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)。
装置:日本電子株式会社製 ECA500
測定モード:逆ゲート付きデカップリング
溶媒:重水素化ジメチルスルホキシド
パルス角度:30°パルス
試料濃度 :30wt%
積算回数 :4000回
前記のように、本発明のフェノール樹脂は、芳香環上にヒドロキシ基を1つ有するモノフェノール化合物(A)と、芳香環上にヒドロキシ基とカルボキシ基とを有する芳香族カルボン酸(B)との反応物である。
本発明のフェノール樹脂は、水酸基と反応する官能基を有する、その他の化合物を併用することで、硬化性樹脂組成物とすることができる。硬化性樹脂組成物は、接着剤や塗料、フォトレジスト、プリント配線基板、半導体封止材料等の各種の電気・電子部材用途に好適に用いることが出来る。
本発明の硬化性樹脂組成物は、半導体封止材料、半導体装置、プリプレグ、プリント回路基板、ビルドアップ基板、ビルドアップフィルム、繊維強化複合材料、繊維強化樹脂成形品、導電ペースト等に適用することができる。
本発明の硬化性樹脂組成物から半導体封止材料を得る方法としては、前記硬化性樹脂組成物、及び無機充填剤等の配合剤とを必要に応じて押出機、ニ-ダ、ロ-ル等を用いて均一になるまで充分に溶融混合する方法が挙げられる。その際、無機充填剤としては、通常、溶融シリカが用いられるが、パワートランジスタ、パワーIC用高熱伝導半導体封止材として用いる場合は、溶融シリカよりも熱伝導率の高い結晶シリカ,アルミナ,窒化ケイ素などの高充填化、または溶融シリカ、結晶性シリカ、アルミナ、窒化ケイ素などを用いるとよい。その充填率は硬化性樹脂組成物100質量部当たり、無機充填剤を30質量部~95質量部の範囲で用いることが好ましく、中でも、難燃性や耐湿性や耐半田クラック性の向上、線膨張係数の低下を図るためには、70質量部以上がより好ましく、80質量部以上であることがさらに好ましい。
本発明の硬化性樹脂組成物から半導体装置を得る方法としては、前記半導体封止材料を注型、或いはトランスファー成形機、射出成形機などを用いて成形し、さらに50~200℃で2~10時間の間、加熱する方法が挙げられる。
本発明の硬化性樹脂組成物からプリプレグを得る方法としては、有機溶剤を配合してワニス化した硬化性樹脂組成物を、補強基材(紙、ガラス布、ガラス不織布、アラミド紙、アラミド布、ガラスマット、ガラスロービング布など)に含浸したのち、用いた溶剤種に応じた加熱温度、好ましくは50~170℃で加熱することによって、得る方法が挙げられる。この時用いる樹脂組成物と補強基材の質量割合としては、特に限定されないが、通常、プリプレグ中の樹脂分が20質量%~60質量%となるように調製することが好ましい。
本発明の硬化性樹脂組成物からプリント回路基板を得る方法としては、前記プリプレグを、常法により積層し、適宜銅箔を重ねて、1~10MPaの加圧下に170~300℃で10分~3時間、加熱圧着させる方法が挙げられる。
本発明の硬化性樹脂組成物からビルドアップ基板を得る方法としては、工程1~3を経由する方法が挙げられる。工程1では、まず、ゴム、フィラーなどを適宜配合した前記硬化性樹脂組成物を、回路を形成した回路基板にスプレーコーティング法、カーテンコーティング法等を用いて塗布した後、硬化させる。工程2では、必要に応じて、硬化性樹脂組成物が塗布された回路基板に所定のスルーホール部等の穴あけを行った後、粗化剤により処理し、その表面を湯洗することによって、前記基板に凹凸を形成させ、銅などの金属をめっき処理する。工程3では、工程1~2の操作を所望に応じて順次繰り返し、樹脂絶縁層及び所定の回路パターンの導体層を交互にビルドアップしてビルドアップ基板を成形する。なお、前記工程において、スルーホール部の穴あけは、最外層の樹脂絶縁層の形成後に行うとよい。また、本発明のビルドアップ基板は、銅箔上で当該樹脂組成物を半硬化させた樹脂付き銅箔を、回路を形成した配線基板上に、170~300℃で加熱圧着することで、粗化面を形成、メッキ処理の工程を省き、ビルドアップ基板を作製することも可能である。
本発明の硬化性樹脂組成物からビルドアップフィルムを得る方法としては、例えば、支持フィルム上に硬化性樹脂組成物を塗布したのち、乾燥させて、支持フィルムの上に樹脂組成物層を形成する方法が挙げられる。本発明の硬化性樹脂組成物をビルドアップフィルムに用いる場合、該フィルムは、真空ラミネート法におけるラミネートの温度条件(通常70℃~140℃)で軟化し、回路基板のラミネートと同時に、回路基板に存在するビアホール或いはスルーホール内の樹脂充填が可能な流動性(樹脂流れ)を示すことが肝要であり、このような特性を発現するよう前記各成分を配合することが好ましい。
本発明の樹脂組成物から繊維強化複合材料(樹脂が強化繊維に含浸したシート状の中間材料)を得る方法としては、樹脂組成物を構成する各成分を均一に混合してワニスを調整し、次いでこれを強化繊維からなる強化基材に含浸した後、重合反応させることにより製造する方法が挙げられる。
本発明の樹脂組成物から繊維強化成形品(樹脂が強化繊維に含浸したシート状部材が硬化した成形品)を得る方法としては、型に繊維骨材を敷き、前記ワニスを多重積層してゆくハンドレイアップ法やスプレーアップ法、オス型・メス型のいずれかを使用し、強化繊維からなる基材にワニスを含浸させながら積み重ねて成形、圧力を成形物に作用させることのできるフレキシブルな型をかぶせ、気密シールしたものを真空(減圧)成型する真空バッグ法、あらかじめ強化繊維を含有するワニスをシート状にしたものを金型で圧縮成型するSMCプレス法、繊維を敷き詰めた合わせ型に前記ワニスを注入するRTM法などにより、強化繊維に前記ワニスを含浸させたプリプレグを製造し、これを大型のオートクレーブで焼き固める方法などが挙げられる。なお、前記で得られた繊維強化樹脂成形品は、強化繊維と樹脂組成物の硬化物とを有する成形品であり、具体的には、繊維強化成形品中の強化繊維の量は、40質量%~70質量%の範囲であることが好ましく、強度の点から50質量%~70質量%の範囲であることが特に好ましい。
本発明の樹脂組成物から導電ペーストを得る方法としては、例えば、微細導電性粒子を該硬化性樹脂組成物中に分散させる方法が挙げられる。前記導電ペーストは、用いる微細導電性粒子の種類によって、回路接続用ペースト樹脂組成物や異方性導電接着剤とすることができる。
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 G2000HXL」
+東ソー株式会社製「TSK-GEL G2000HXL」
+東ソー株式会社製「TSK-GEL G3000HXL」
+東ソー株式会社製「TSK-GEL G4000HXL」
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ワークステーション EcoSEC-WorkStation」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)。
装置:日本電子株式会社製 AL-400
測定モード:逆ゲート付きデカップリング
溶媒:重水素化ジメチルスルホキシド
パルス角度:30°パルス
試料濃度 :30wt%
積算回数 :4000回
温度計、分留管、冷却管、撹拌器を取り付けたフラスコに窒素ガスパージを施しながらフェノール565g(6モル)、p-ヒドロキシ安息香酸207g(1.5モル)、p-トルエンスルホン酸二水和物7.7g、トルエン207gを仕込んだ。水を分留管で捕集しながら140℃に昇温し、12時間反応させた。反応終了後、49%水酸化ナトリウム水溶液3.4gを加え中和確認し、トルエン685gを加えて80℃まで冷却し、水207gで水洗を4回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒と未反応モノマーを減圧下で留去してフェノール樹脂(1)を得た。得られたフェノール樹脂(1)の融点は175℃であった。フェノール樹脂(1)のGPCチャートを図1に、13C-NMRチャートを図2に、MSスペクトルを図3に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)との合計のピーク面積は86%、モノフェノール残は1.7%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.06であった。
フェノールをオルソクレゾール649g(6モル)、反応温度を150℃に変更した以外は実施例1と同様にして、フェノール樹脂(2)を得た。得られたフェノール樹脂(2)の融点は135℃であった。フェノール樹脂(2)のGPCチャートを図4に、13C-NMRチャートを図5に、MSスペクトルを図6に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は91%、モノフェノール残は0.1%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.05であった
フェノールをパラクレゾール649g(6モル)、反応温度を150℃に変更した以外は実施例1と同様にして、フェノール樹脂(3)を得た。得られたフェノール樹脂(3)の融点は165℃であった。フェノール樹脂(3)のGPCチャートを図7に、13C-NMRチャートを図8に、MSスペクトルを図9に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は88%、モノフェノール残は6.5%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.02であった。
フェノールをメタクレゾール649g(6モル)、反応温度を150℃に変更した以外は実施例1と同様にして、フェノール樹脂(4)を得た。得られたフェノール樹脂(4)の融点は130℃であった。フェノール樹脂(4)のGPCチャートを図10に、13C-NMRチャートを図11に、MSスペクトルを図12に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は86%、モノフェノール残は6.2%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.10であった。
フェノールを2,6-キシレノール733g(6モル)、反応温度を160℃に変更した以外は実施例1と同様にして、フェノール樹脂(5)を得た。得られたフェノール樹脂(5)の融点は176℃であった。フェノール樹脂(5)のGPCチャートを図13に、13C-NMRチャートを図14に、MSスペクトルを図15に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は93%、モノフェノール残は0.2%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.03であった。
フェノールを2,4-キシレノール733g(6モル)、反応温度を160℃に変更した以外は実施例1と同様にして、フェノール樹脂(6)を得た。得られたフェノール樹脂(6)の融点は155℃であった。フェノール樹脂(6)のGPCチャートを図16に、13C-NMRチャートを図17に、MSスペクトルを図18に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は97%、モノフェノール残は0.1%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.03であった。
p-ヒドロキシ安息香酸をサリチル酸207g(1.5モル)に、p-トルエンスルホン酸二水和物を15.4gに、反応温度を180℃に変更した以外は実施例1と同様にして、フェノール樹脂(7)を得た。得られたフェノール樹脂(7)の融点は40℃であった。フェノール樹脂(7)のGPCチャートを図19に、13C-NMRチャートを図20に、MSスペクトルを図21に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は98%、モノフェノール残は0.1%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.01であった。
p-ヒドロキシ安息香酸をサリチル酸207g(1.5モル)に、p-トルエンスルホン酸二水和物を15.4gに、反応温度を180℃に変更した以外は実施例2と同様にして、フェノール樹脂(8)を得た。得られたフェノール樹脂(8)の融点は83℃であった。フェノール樹脂(8)のGPCチャートを図22に、13C-NMRチャートを図23に、MSスペクトルを図24に示す。GPCから構造式(1)で表されるエステル化合物と、構造式(2)で表されるケトン化合物(2)の合計ピーク面積は97%、モノフェノール残は0.1%であった。また13C-NMRからエステル基:ケトン基の比率は1:0.02であった。
表1に示す組成で配合して硬化性樹脂組成物を得た。これを11cm×9cm×2.4mmの型枠に流し込み、プレスで175℃の温度で1時間成型した後、175℃の温度で5時間後硬化して硬化物を作製した。得られた硬化物について、熱時弾性率、誘電正接、吸湿率を測定した。結果を表1の下部に示す。
・HE100C-15:フェニルアラルキル型フェノール樹脂、水酸基当量:174g/eq(エア・ウォーター株式会社製)
・N-655-EXP-S:クレゾールノボラック型エポキシ樹脂、エポキシ当量201g/eq(DIC株式会社製)
・TPP:トリフェニルホスフィン
前記で作製した厚さ2.4mmの硬化物を幅5mm、長さ54mmのサイズに切り出し、この試験片を粘弾性測定装置(DMA:レオメトリック社製固体粘弾性測定装置「RSAII」、レクタンギュラーテンション法:周波数1Hz、昇温速度3℃/分)を用いて、260℃での貯蔵弾性率を熱時弾性率として測定した。
先で得た硬化物を105℃で2時間加熱真空乾燥させた後、温度23℃、湿度50%の室内に24時間保管したものを試験片とした。アジレント・テクノロジー株式会社製「ネットワークアナライザE8362C」を用い、空洞共振法により試験片の1GHzでの誘電正接を測定した。
前記で作製した厚さ2.4mmの硬化物を幅25mm、長さ75mmのサイズに切り出し、85℃/85%RHの恒温恒湿装置中で300時間処理した前後の質量変化(wt%)を吸湿率として測定した。
表2に示す組成比で2本ロールを用いて90℃の温度で5分間溶融混練して組成物を調製した。得られた組成物について、下記に従い、流動性(スパイラルフロー)と難燃性を評価した。
硬化性樹脂組成物を試験用金型に注入し、温度175℃、注入圧力70kg/cm2、300秒の条件でスパイラルフロー値を測定した。
硬化性樹脂組成物をトランスファー成型機にて幅12.7mm、長さ127mm、厚み1.6mmのサンプル175℃で5分間成形した後、175℃で5時間後硬化して評価用サンプルを作成した。そのサンプル5本を用い、UL-94試験法に準拠して燃焼試験を行った。
※1:1回の接炎における最大燃焼時間(秒)
※2:試験片5本の合計燃焼時間(秒)
・HE100C-15:フェニルアラルキル型フェノール樹脂、水酸基当量:174g/eq(エア・ウォーター株式会社製)
・N-655-EXP-S:クレゾールノボラック型エポキシ樹脂、エポキシ当量201g/eq(DIC株式会社製)
・TPP:トリフェニルホスフィン
・溶融シリカ:球状シリカ「FB-5604」デンカ株式会社製
・シランカップリング剤:γ-グリシドキシトリエトキシキシシラン「KBM-403」信越化学工業株式会社製
・カルナウバワックス:「PEARL WAX No.1-P」デンカ株式会社製
Claims (16)
- 前記式(1)及び(2)中のR1~R17が、水素原子又はメチル基である請求項1記載のフェノール樹脂。
- 前記フェノール樹脂中のエステル基とケトン基との比率が、13C-NMR測定による比率として1:0.01~1:0.20の範囲である請求項1又は2記載のフェノール樹脂。
- 前記芳香環上にヒドロキシ基を1つ有するモノフェノール化合物(A)が、フェノール、クレゾール又はキシレノールであり、前記芳香環上にヒドロキシ基とカルボキシ基とを有する芳香族カルボン酸(B)がモノヒドロキシ安息香酸である請求項1~3の何れか1項記載のフェノール樹脂。
- エポキシ樹脂用硬化剤である請求項1~4の何れか1項記載のフェノール樹脂。
- 請求項1~4の何れか1項記載のフェノール樹脂と、水酸基と反応する官能基を有する樹脂とを必須成分とする硬化性樹脂組成物。
- 前記水酸基と反応する官能基を有する樹脂がエポキシ樹脂である請求項6記載の硬化性樹脂組成物
- 更に、硬化触媒としてリン系化合物及び/又は含窒素化合物を含有する請求項7記載の硬化性樹脂組成物。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物の硬化物。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物と無機充填材とを含有する半導体封止材料。
- 請求項10に記載の半導体封止材料の硬化物である半導体装置。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物と補強基材とを有する含浸基材の半硬化物であるプリプレグ。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物の板状賦形物と銅箔とからなる回路基板。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物の硬化物と基材フィルムとからなるビルドアップフィルム。
- 請求項6~8の何れか1項記載の硬化性樹脂組成物と強化繊維とを含有する繊維強化複合材料。
- 請求項15記載の繊維強化複合材料の硬化物である繊維強化成形品。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56120642A (en) * | 1980-02-29 | 1981-09-22 | Teijin Ltd | Preparation of aryl ester of aromatic oxycarboxylic acid |
JPS57154140A (en) * | 1981-02-04 | 1982-09-22 | Ici Ltd | Manufacture of hydroxyarylophenone |
JP2012519172A (ja) * | 2009-02-26 | 2012-08-23 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 3,4’ジアセトキシベンゾフェノン製造用中間体としての3,4’ジヒドロキシベンゾフェノンの製造方法 |
WO2018003513A1 (ja) * | 2016-06-29 | 2018-01-04 | Dic株式会社 | フェノールノボラック樹脂、硬化性樹脂組成物及びその硬化物 |
JP2018100319A (ja) * | 2016-12-19 | 2018-06-28 | Dic株式会社 | フェノール樹脂、硬化性樹脂組成物及びその硬化物 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1013534A (en) * | 1961-07-03 | 1965-12-15 | Gen Aniline & Film Corp | New benzophenone compound and compositions stabilized therewith |
JPS62292741A (ja) * | 1986-06-13 | 1987-12-19 | Toray Ind Inc | 新規フエノ−ル性化合物及びエポキシ硬化剤 |
JP2752498B2 (ja) * | 1989-12-06 | 1998-05-18 | 帝人株式会社 | ヒドロキシカルボン酸誘導体の製造方法 |
JPH09291064A (ja) * | 1996-04-25 | 1997-11-11 | Sumitomo Chem Co Ltd | アリールエステル化合物およびそれを用いたエポキシ樹脂組成物 |
CN1272301C (zh) * | 2005-04-28 | 2006-08-30 | 武汉大学 | 4,4'-二羟基二苯甲酮的制备方法 |
CN101460539A (zh) * | 2006-06-06 | 2009-06-17 | 日立化成工业株式会社 | 具有酸性取代基和不饱和马来酰亚胺基的固化剂的制造方法以及热固化性树脂组合物、预浸料及层叠板 |
WO2011045941A1 (ja) * | 2009-10-16 | 2011-04-21 | 日本曹達株式会社 | エポキシ硬化樹脂形成用組成物及びその硬化物 |
JP5757879B2 (ja) * | 2010-01-29 | 2015-08-05 | 日本化薬株式会社 | フェノール化合物、エポキシ樹脂、エポキシ樹脂組成物、プリプレグおよびそれらの硬化物 |
JP5457304B2 (ja) * | 2010-08-26 | 2014-04-02 | 新日鉄住金化学株式会社 | フェノール性樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及び硬化物 |
JP5839649B2 (ja) * | 2010-10-14 | 2016-01-06 | Dic株式会社 | 硬化性コーティング組成物、積層ポリエステル樹脂フィルム及び太陽電池バックシート |
CN103497092A (zh) * | 2013-10-12 | 2014-01-08 | 武汉怡兴化工有限公司 | 4,4′-二羟基二苯甲酮制备方法 |
JP6332720B1 (ja) | 2016-07-06 | 2018-05-30 | Dic株式会社 | 活性エステル樹脂とその硬化物 |
CN107129432B (zh) * | 2017-06-06 | 2020-11-03 | 如东金康泰化学有限公司 | 一种紫外线吸收剂4,4’-二已氧基二苯甲酮的合成方法 |
-
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56120642A (en) * | 1980-02-29 | 1981-09-22 | Teijin Ltd | Preparation of aryl ester of aromatic oxycarboxylic acid |
JPS57154140A (en) * | 1981-02-04 | 1982-09-22 | Ici Ltd | Manufacture of hydroxyarylophenone |
JP2012519172A (ja) * | 2009-02-26 | 2012-08-23 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 3,4’ジアセトキシベンゾフェノン製造用中間体としての3,4’ジヒドロキシベンゾフェノンの製造方法 |
WO2018003513A1 (ja) * | 2016-06-29 | 2018-01-04 | Dic株式会社 | フェノールノボラック樹脂、硬化性樹脂組成物及びその硬化物 |
JP2018100319A (ja) * | 2016-12-19 | 2018-06-28 | Dic株式会社 | フェノール樹脂、硬化性樹脂組成物及びその硬化物 |
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