WO2015053298A1 - Phenolic resin, epoxy resin, epoxy resin composition, prepreg and cured product of said epoxy resin composition or prepreg - Google Patents
Phenolic resin, epoxy resin, epoxy resin composition, prepreg and cured product of said epoxy resin composition or prepreg Download PDFInfo
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- WO2015053298A1 WO2015053298A1 PCT/JP2014/076877 JP2014076877W WO2015053298A1 WO 2015053298 A1 WO2015053298 A1 WO 2015053298A1 JP 2014076877 W JP2014076877 W JP 2014076877W WO 2015053298 A1 WO2015053298 A1 WO 2015053298A1
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- WIPO (PCT)
- Prior art keywords
- epoxy resin
- group
- substituted
- carbon atoms
- resin composition
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 110
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 110
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title abstract description 9
- 229920001568 phenolic resin Polymers 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011574 phosphorus Substances 0.000 claims abstract description 14
- -1 phenol compound Chemical class 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000004065 semiconductor Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 abstract description 22
- 239000000470 constituent Substances 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000002904 solvent Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000011256 inorganic filler Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 238000006735 epoxidation reaction Methods 0.000 description 7
- 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 7
- 229910003475 inorganic filler Inorganic materials 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SULYEHHGGXARJS-UHFFFAOYSA-N 2',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1O SULYEHHGGXARJS-UHFFFAOYSA-N 0.000 description 2
- YNPDFBFVMJNGKZ-UHFFFAOYSA-N 2'-Hydroxy-5'-methylacetophenone Chemical compound CC(=O)C1=CC(C)=CC=C1O YNPDFBFVMJNGKZ-UHFFFAOYSA-N 0.000 description 2
- IXWOUPGDGMCKGT-UHFFFAOYSA-N 2,3-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1O IXWOUPGDGMCKGT-UHFFFAOYSA-N 0.000 description 2
- WNCNWLVQSHZVKV-UHFFFAOYSA-N 2,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C=C1O WNCNWLVQSHZVKV-UHFFFAOYSA-N 0.000 description 2
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- UCQUAMAQHHEXGD-UHFFFAOYSA-N 3',4'-dihydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C(O)=C1 UCQUAMAQHHEXGD-UHFFFAOYSA-N 0.000 description 2
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 description 2
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 description 2
- FEUATHOQKVGPEK-UHFFFAOYSA-N 4-hydroxybenzene-1,3-dicarbaldehyde Chemical compound OC1=CC=C(C=O)C=C1C=O FEUATHOQKVGPEK-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- OJOBTAOGJIWAGB-UHFFFAOYSA-N acetosyringone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1O OJOBTAOGJIWAGB-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTZFYYHCGSXJV-UHFFFAOYSA-N isovanillin Chemical compound COC1=CC=C(C=O)C=C1O JVTZFYYHCGSXJV-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical class C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Chemical class CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RKMJXTWHATWGNX-UHFFFAOYSA-N decyltrimethylammonium ion Chemical class CCCCCCCCCC[N+](C)(C)C RKMJXTWHATWGNX-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical class C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GVYLCNUFSHDAAW-UHFFFAOYSA-N mirex Chemical compound ClC12C(Cl)(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl GVYLCNUFSHDAAW-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 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
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 description 1
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0281—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing phosphorus in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
- C08G59/304—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
- C08G59/3272—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen containing phosphorus
-
- 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
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the present invention relates to a novel phenol resin, epoxy resin and epoxy resin composition. Moreover, it is related with hardened
- Epoxy resin compositions are widely used in the fields of electrical and electronic parts, structural materials, adhesives, paints, etc. due to their workability and excellent electrical properties, heat resistance, adhesion, moisture resistance (water resistance), etc. It has been.
- Japanese Unexamined Patent Publication No. 11-323162 Japanese Unexamined Patent Publication No. 2004-2573 Japanese Unexamined Patent Publication No. 2006-63315 Japanese Unexamined Patent Publication No. 2003-137971 International Publication No. 2011/093474 Pamphlet
- the present invention has been made as a result of studies to solve such problems, and in the cured product, a phenol resin which is a constituent of an epoxy resin composition having high heat resistance and high flame retardancy, and the phenol resin
- the epoxy resin derived from the above, the phenol resin, the epoxy resin composition containing the epoxy resin, the prepreg, and the cured product thereof are provided.
- the present invention relates to the following (1) to (7).
- each R 1 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or It represents either a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, m represents the number of R 1 , and is an integer of 0 to 4.
- each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, Any one of a formyl group, an allyl group, or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, k represents the number of R 2 , and is an integer of 0 to 4)
- each R 3 independently represents a hydrogen atom, an alkyl group or an aromatic group.
- each R 1 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or Represents a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms
- each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 6 to 6 carbon atoms
- 10 represents a substituted or unsubstituted aryl group, a hydroxyl group, a nitro group, a formyl group, an allyl group, or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms
- k represents the number of R 2 , 0 Is an integer of ⁇ 4, m is the number of R 1 , is an integer of 0
- each R 3 independently represents a hydrogen atom, an alkyl group or an aromatic group.
- An epoxy resin composition comprising the phenol resin and the epoxy resin according to (1) or (2).
- a prepreg comprising the epoxy resin composition according to (4) above and a sheet-like fiber base material.
- the phenolic resin of the present invention contains a mesogenic group-containing epoxy resin with high purity, a cured product of an epoxy resin composition containing the phenolic resin as a constituent component exhibits excellent heat resistance and flame retardancy, and is encapsulated in a semiconductor. It is useful when used for materials, various composite materials including prepregs, adhesives, paints and the like.
- the phenol resin (b) of the present invention is obtained by obtaining a phenol compound (a) by a reaction between a phenol compound represented by the following formula (1) and a compound represented by the following formula (2). It can be obtained by reacting the phosphorus-containing compound represented by (3).
- each R 1 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or It represents either a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, m represents the number of R 1 , and is an integer of 0 to 4.
- each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, Any one of a formyl group, an allyl group, or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, k represents the number of R 2 , and is an integer of 0 to 4)
- each R 3 independently represents a hydrogen atom, an alkyl group or an aromatic group.
- the phenol compound (a) is obtained by a reaction between the compound represented by the above formula (1) and the compound represented by the above formula (2).
- each R 1 is independently present and is a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or a carbon number A 1 to 10 unsubstituted alkoxy group is preferred.
- Specific examples of the compound represented by the formula (1) used for the reaction with the compound represented by the formula (2) in order to obtain the phenol compound (a) include 2-hydroxyacetophenone, 3-hydroxyacetophenone, 4-hydroxyacetophenone, 2 ′, 4′-dihydroxyacetophenone, 2 ′, 5′-dihydroxyacetophenone, 3 ′, 4′-dihydroxyacetophenone, 3 ′, 5′-dihydroxyacetophenone, 2 ′, 3 ′, 4′- Trihydroxyacetophenone, 2 ′, 4 ′, 6′-trihydroxyacetophenone monohydrate, 4′-hydroxy-3′-methylacetophenone, 4′-hydroxy-2′-methylacetophenone, 2′-hydroxy-5 ′ -Methylacetophenone, 4'-hydroxy-3'-methoxyacetophenone, 2 -Hydroxy-4'-methoxyacetophenone, 4'-hydroxy-3'-nitroacetophenone, 4'-hydroxy-3 ', 5'-
- Specific examples of the compound represented by the formula (2) used for the reaction with the compound represented by the formula (1) in order to obtain the phenol compound (a) include, for example, 2-hydroxybenzaldehyde, 3-hydroxy Benzaldehyde, 4-hydroxybenzaldehyde, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, 2,5-dihydroxybenzaldehyde, 3,4-dihydroxybenzaldehyde, syringaldehyde, 3,5-di-tert-butyl-4 -Hydroxybenzaldehyde, isovanillin, 4-hydroxy-3-nitrobenzaldehyde, 5-hydroxy-2-nitrobenzaldehyde, 3,4-dihydroxy-5-nitrobenzaldehyde, vanillin, o-vanillin, 2-hydroxy-1-naphthaldehyde 2-hydroxy-5-nitro-m-anisaldehyde, 2-hydroxy-5-methylisophthalaldehyde, 2-hydroxy
- the phenol compound (a) is obtained by an aldol condensation reaction between one or more compounds represented by the formula (1) and a compound represented by the formula (2) under acidic conditions or basic conditions.
- the compound represented by the formula (2) is used in an amount of 1.0 to 1.05 mol with respect to 1 mol of the compound represented by the formula (1).
- examples of the acidic catalyst that can be used include inorganic acids such as hydrochloric acid, sulfuric acid, and nitric acid, and organic acids such as toluenesulfonic acid, xylenesulfonic acid, and oxalic acid. These may be used alone or in combination of a plurality of types.
- the amount of the acidic catalyst used is 0.01 to 1.0 mol, preferably 0.2 to 0.5 mol, per 1 mol of the compound represented by the formula (2).
- usable basic catalysts include metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal carbonates such as potassium carbonate and sodium carbonate, diethylamine, Examples include amine derivatives such as triethylamine, tributylamine, diisobutylamine, pyridine and piperidine, and amino alcohol derivatives such as dimethylaminoethyl alcohol and diethylaminoethyl alcohol. Also in the case of basic conditions, the basic catalysts listed above may be used alone, or a plurality of types may be used in combination. The amount of the basic catalyst used is 0.1 to 2.5 mol, preferably 0.2 to 2.0 mol, per 1 mol of the compound represented by the formula (2).
- a solvent may be used as necessary.
- the solvent that can be used is not particularly limited as long as it is not reactive with the compound represented by the formula (2) such as ketones, but the compound represented by the formula (2) as a raw material can be easily used. It is preferable to use alcohols as the solvent in terms of dissolution in the solvent.
- the reaction temperature is usually 10 to 90 ° C., preferably 35 to 70 ° C.
- the reaction time is usually 0.5 to 10 hours, but is not limited to this because the reactivity varies depending on the type of raw material compound.
- an unreacted substance, a solvent, etc. are removed from a reaction liquid under heating and pressure reduction, after washing
- crystallization a crystal
- the produced phenol compound may dissolve in water, so that it is precipitated as crystals under neutral to acidic conditions by adding hydrochloric acid or the like.
- the phenol resin (b) of the present invention can be obtained by subjecting the phenol compound (a) to an addition reaction with the phosphorus-containing compound represented by the above formula (3).
- the compound represented by the above formula (3) can be obtained, for example, as HCA (manufactured by Sanko Co., Ltd.).
- the production method of the phenol resin (b) of the present invention is specifically described. It is preferable to add the phenol compound (a) dropwise or dividedly into the phosphorus-containing compound while paying attention to heat generation. At this time, an organic solvent may be used as a reaction solvent.
- the temperature at which the phenol compound (a) is dropped into the phosphorus-containing compound is preferably 20 ° C. to 200 ° C., and is particularly preferably 50 ° C. to 160 ° C. in terms of reactivity control and ease of removal of reaction heat. preferable.
- a phosphorus containing compound is phenol compound ( It is preferably used in an amount of 1 equivalent or more (for example, 1 to 5 equivalents) relative to 1 equivalent of the olefin group of a).
- the obtained compound when used as a curing agent for epoxy resin, it may be used while removing an excessive phosphorus-containing compound, or it may be used after removal, but finally cured.
- the phosphorus atom-containing phenol compound of the present invention is contained in at least 50 parts by weight or more in a total of 100 parts by weight of the phosphorus atom-containing phenol compound of the present invention and the phosphorus-containing compound. It is particularly preferable that the content is 80 parts by weight or more.
- the organic solvent is not particularly limited.
- those that are inert to a phosphorus-containing compound and a phenol compound (a) are preferable.
- aliphatic alcohols, aromatic hydrocarbons or These mixed solvents are used.
- methanol, ethanol, isopropyl alcohol, n-propyl alcohol, t-butyl alcohol, isobutyl alcohol examples thereof include n-butyl alcohol, ethylene glycol lower alkyl ethers, and propylene glycol lower alkyl ethers.
- aromatic hydrocarbon solvent examples include toluene, xylene, cumene and the like.
- Such a solvent is usually used in the range of 20 to 500 parts by weight with respect to 100 parts by weight of the total phosphorus-containing compound to be used, but is not limited thereto.
- the phenol resin (b) of the present invention thus obtained has a structure represented by the following formula (4).
- R 1 , R 2 , k and m are the same as in the formulas (1) to (2), Z represents a hydrogen atom or a structure of the following formula (5), and a plurality of Z (At least one of them represents the structure of the following formula (5).)
- R 3 is the same as Formula (3).
- the hydroxyl equivalent of the phenol resin (b) of the present invention is 200 to 800 g / eq. Is preferred, 220 to 750 g / eq. Is more preferable.
- the softening point is preferably 100 to 150 ° C.
- the epoxy resin of the present invention can be obtained by reacting the phenol resin (b) of the present invention obtained by the above method with an epihalohydrin in an alcohol solvent and epoxidizing it.
- an epihalohydrin in an alcohol solvent and epoxidizing it.
- only 1 type of the phenol resin (b) of this invention may be used, or 2 or more types may be used together.
- a phenol compound other than the phenol resin (b) that can be used in combination any phenol compound that is usually used as a raw material for an epoxy resin can be used without particular limitation.
- the epoxy resin of the present invention is represented by the compound represented by the formula (2) and the formula (1) because a cured product exhibiting particularly excellent solvent solubility and having high flame retardancy can be obtained.
- the epoxidized product of the phenol resin (b) of the present invention obtained by reacting the phenol compound (a) obtained by the reaction with the compound and the phosphorus-containing compound represented by the formula (3) is preferred.
- epichlorohydrin, ⁇ -methylepichlorohydrin, ⁇ -methylepichlorohydrin, epibromohydrin and the like can be used as the epihalohydrin, and epichlorohydrin which is easily available industrially is preferable.
- the amount of epihalohydrin used is usually 2 to 20 mol, preferably 2 to 15 mol, particularly preferably 2 to 4.5 mol, per mol of the hydroxyl group of the phenol resin (b).
- the epoxy resin is obtained by a reaction in which the phenol resin (b) and epihalohydrin are added in the presence of an alkali metal oxide, and then the resulting 1,2-halohydrin ether group is opened to epoxidize.
- epihalohydrin in an amount significantly smaller than usual as described above, the molecular weight of the epoxy resin can be increased and the molecular weight distribution can be broadened.
- the resulting epoxy resin can be removed from the system as a resinous material having a relatively low softening point, and exhibits excellent solvent solubility.
- an aprotic polar solvent such as alcohols such as methanol, ethanol and isopropyl alcohol, dimethyl sulfone, dimethyl sulfoxide, tetrahydrofuran and dioxane.
- alcohols are preferable, and the ionic reaction at the time of epoxidation can be efficiently advanced by the polarity of the alcohol solvent, and an epoxy resin can be obtained with high purity.
- the ⁇ , ⁇ -unsaturated carbonyl moiety shows high reactivity and tends to decompose, but since it is solvated by using an alcohol solvent, the decomposition reaction It becomes difficult to receive.
- the alcohol solvent that can be used, methanol, ethanol, and isopropyl alcohol are preferable. Among these, it is particularly preferable to use methanol from the viewpoint of compatibility with the epoxy resin.
- the amount used is usually 2 to 50% by mass, preferably 4 to 35% by mass, based on the amount of epihalohydrin used.
- an aprotic polar solvent is used, it is usually 5 to 100% by mass, preferably 10 to 80% by mass, based on the amount of epihalohydrin used.
- Alkali metal hydroxides can be used in the epoxidation reaction.
- Examples of the alkali metal hydroxide that can be used for the epoxidation reaction include sodium hydroxide, potassium hydroxide, and the like, and these may be used as they are, or an aqueous solution thereof may be used.
- an aqueous solution the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system and separated from a mixture of water and epihalohydrin distilled continuously under reduced pressure or normal pressure. Alternatively, water may be removed and only the epihalohydrin is continuously returned to the reaction system.
- the amount of the alkali metal hydroxide used is usually 0.9 to 3.0 mol, preferably 1.0 to 2.5 mol, more preferably 1 with respect to 1 mol of the hydroxyl group of the phenol resin (b) of the present invention.
- the amount is from 0.0 to 2.0 mol, particularly preferably from 1.0 to 1.3 mol.
- the present inventors remarkably reduce the amount of halogen contained in the epoxy resin obtained by using flaky sodium hydroxide in the epoxidation reaction, rather than using sodium hydroxide as an aqueous solution. It came to know that it became possible.
- the flaky sodium hydroxide is preferably added in portions in the reaction system. By performing divided addition, it is possible to prevent a rapid decrease in the reaction temperature, thereby preventing the formation of impurities such as 1,3-halohydrin and halomethylene.
- a quaternary ammonium salt such as tetramethylammonium chloride, tetramethylammonium bromide, trimethylbenzylammonium chloride as a catalyst.
- the amount of the quaternary ammonium salt used is usually 0.1 to 15 g, preferably 0.2 to 10 g, based on 1 mol of the hydroxyl group of the phenol resin of the present invention.
- the reaction temperature is usually 30 to 90 ° C, preferably 35 to 80 ° C.
- the reaction time is usually 0.5 to 10 hours, preferably 1 to 8 hours.
- an alcohol solvent it is preferably 50 ° C. to 90 ° C., more preferably 60 to 85 ° C., and particularly preferably 70 to 80 ° C.
- the recovered epoxy resin of the present invention is dissolved in a solvent such as toluene or methyl isobutyl ketone, and an alkali metal such as sodium hydroxide or potassium hydroxide.
- the reaction can be carried out by adding an aqueous solution of hydroxide to ensure ring closure.
- the amount of the alkali metal hydroxide used is usually 0.01 to 0.3 mol, preferably 0.05 to 0.2 mol, relative to 1 mol of the hydroxyl group of the phenol resin of the present invention.
- the reaction temperature is usually 50 to 120 ° C., and the reaction time is usually 0.5 to 2 hours.
- the produced salt is removed by filtration, washing with water, etc., and the solvent is distilled off under reduced pressure by heating to obtain the epoxy resin of the present invention.
- the epoxy resin of this invention precipitates as a crystal
- the total halogen content of the epoxy resin of the present invention obtained by using flaky sodium hydroxide is usually 1800 ppm or less, preferably 1600 ppm or less, more preferably 1300 ppm or less. If the total halogen content is too large, the electrical reliability of the cured product may be adversely affected.
- the epoxy resin composition of the present invention contains at least one of the epoxy resin of the present invention and the phenol resin of the present invention as an essential component.
- the epoxy resin of the present invention when the epoxy resin of the present invention is contained as an essential component, the epoxy resin of the present invention can be used alone or in combination with other epoxy resins.
- epoxy resins include bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, bisphenol I, etc.) and phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted) Naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene and dihydroxynaphthalene) and various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.) Of polycondensates with benzene, aromatic compounds such as xylene and formaldehy
- the proportion of the epoxy resin of the present invention in the total epoxy resin component in the epoxy resin composition of the present invention is preferably 30% by mass or more, more preferably 40% by mass or more, and 70% by mass. The above is more preferable, and 100% by mass (when no other epoxy resin is used in combination) is particularly preferable.
- the epoxy resin of the present invention is used as a modifier for the epoxy resin composition, it is added in a proportion of 1 to 30% by mass in the total epoxy resin.
- the epoxy resin composition of the present invention contains the epoxy resin of the present invention as an essential component, it is preferable to use a curing agent.
- the curing agent that can be used may be the above-described phenolic resin of the present invention or other curing agent.
- other curing agents include amine compounds, acid anhydride compounds, amide compounds, and phenol compounds. Specific examples of these other curing agents are shown in the following (a) to (e).
- Phenol compounds Polyhydric phenols (bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, terpene diphenol, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 3,3 ', 5, 5′-tetramethyl- (1,1′-biphenyl) -4,4′-diol, hydroquinone, resorcin, naphthalenediol, tris- (4-hydroxyphenyl) methane and 1,1,2,2-tetrakis (4 -Hydroxyphenyl) ethane, etc .; phenols (eg, phenol, alkyl-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene and dihydroxynaphthalene) and aldehydes (formaldehyde, acetaldehyde, benzaldehyde, p
- active hydrogen such as amine compounds such as diaminodiphenylmethane, diaminodiphenylsulfone and naphthalenediamine, and condensates of catechol with aldehydes, ketones, dienes, substituted biphenyls or substituted phenyls.
- a curing agent having a structure in which groups are adjacent is preferable because it contributes to the arrangement of the epoxy resin.
- Other curing agents may be used alone or in combination.
- the phenol resin of the present invention when used as a curing agent, other curing agents may be used in combination with the phenol resin of the present invention.
- the curing agent used in combination include the same amine compounds, acid anhydride compounds, amide compounds, and phenol compounds as described above.
- the proportion of the phenol resin of the present invention in the total curing agent component in the epoxy resin composition of the present invention is preferably 5% by mass or more, more preferably 10% by mass or more, and 30% by mass. The above is more preferable.
- the use amount of the total curing agent containing the phenol compound of the present invention is preferably 0.5 to 2.0 equivalents relative to 1 equivalent of the epoxy groups of all epoxy resins, 0.6 to 1.5 equivalents are particularly preferred.
- a curing accelerator may be added to the epoxy resin composition of the present invention.
- the curing accelerator include phosphines such as triphenylphosphine and bis (methoxyphenyl) phenylphosphine, imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-ethylimidazole and 4-methylimidazole, Tertiary amines such as 2- (dimethylaminomethyl) phenol, trisdimethylaminomethylphenol, diazabicycloundecene, tetrabutylammonium salt, triisopropylmethylammonium salt, trimethyldecanylammonium salt, cetyltrimethylammonium salt, etc.
- Quaternary phosphonium salts such as quaternary ammonium salts, triphenylbenzyl phosphonium salts, triphenylethyl phosphonium salts, tetrabutyl phosphonium salts (the counter ions of quaternary salts are halogens) , Organic acid ions, hydroxide ions and the like are not particularly specified, but organic acid ions and hydroxide ions are particularly preferable.), Metal compounds such as tin octylate, etc. are exemplified.
- the amount of the curing accelerator used is usually 0.2 to 5.0 parts by weight, preferably 0.2 to 4.0 parts by weight per 100 parts by weight of the epoxy resin.
- An inorganic filler can be added to the epoxy resin composition of the present invention (hereinafter also referred to as curable resin composition) as necessary.
- examples of inorganic fillers include crystalline silica, fused silica, alumina, zircon, calcium silicate, calcium carbonate, silicon carbide, silicon nitride, boron nitride, zirconia, fosterite, steatite, spinel, titania, talc, and the like.
- the present invention is not limited to these. These may be used alone or in combination of two or more.
- the content of these inorganic fillers is used in an amount of 0 to 95% by weight in the curable resin composition of the present invention.
- the curable resin composition of the present invention includes various agents such as silane coupling agents, mold release agents such as stearic acid, palmitic acid, zinc stearate, and calcium stearate, surfactants, dyes, pigments, and ultraviolet absorbers.
- agents such as silane coupling agents, mold release agents such as stearic acid, palmitic acid, zinc stearate, and calcium stearate, surfactants, dyes, pigments, and ultraviolet absorbers.
- a compounding agent and various thermosetting resins can be added.
- thermosetting resins and thermoplastic resins include vinyl ester resins, unsaturated polyester resins, maleimide resins, cyanate resins, isocyanate compounds, benzoxazine compounds, vinyl benzyl ether compounds, polybutadiene and its modified products, and acrylonitrile.
- thermosetting resin or thermoplastic resin is used in an amount occupying 60% by mass or less in the epoxy resin composition of the present invention.
- the epoxy resin composition of the present invention can be obtained by uniformly mixing the above-mentioned components, and preferred applications thereof include semiconductor encapsulants and printed wiring boards.
- the epoxy resin composition of the present invention can be easily made into a cured product by the same method as conventionally known.
- an epoxy resin that is an essential component of the epoxy resin composition of the present invention, a curing agent and an inorganic filler, and, if necessary, a curing accelerator, a compounding agent, various thermosetting resins and various thermoplastic resins, as necessary the epoxy resin composition of the present invention obtained by thoroughly mixing until uniform using an extruder, kneader, roll, etc.
- the cured product of the epoxy resin composition of the present invention can be obtained by molding and further heating for 2 to 10 hours above the melting point.
- the epoxy resin composition of the present invention can be used for semiconductor sealing applications.
- the epoxy resin composition of this invention can also be made into the varnish containing a solvent.
- the varnish includes, for example, a mixture containing the epoxy resin of the present invention or the phenol resin of the present invention in at least one of an epoxy resin and a curing agent, and optionally containing other components such as an inorganic filler.
- the amount of the solvent is usually 10 to 95% by mass, preferably 15 to 85% by mass, based on the entire varnish.
- the varnish obtained as described above is impregnated into a fiber substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber and paper, and then the solvent is removed by heating, and the epoxy resin composition of the present invention By making a semi-cured state, the prepreg of the present invention can be obtained.
- the “semi-cured state” means a state in which an epoxy group which is a reactive functional group partially remains unreacted.
- the prepreg can be hot press molded to obtain a cured product.
- Example 1 178 parts of HCA (manufactured by Sanko Co., Ltd.) and 360 parts of xylene were added to a flask equipped with a stirrer, a reflux condenser and a stirrer while purging with nitrogen, and heated to 100 ° C. Thereto, 200 parts of the phenol compound (a) was dividedly added over 1 hour, then heated to 130 ° C. and heated to reflux for 10 hours. After adding 180 parts of ethanol to the reaction product, the solvent was distilled off under reduced pressure with an evaporator to obtain 320 g of the phenol resin (b) (P1) of the present invention. The obtained phenol resin (b) had a hydroxyl group equivalent of 243 g / eq and a softening point of 135.8 ° C.
- Example 2 A flask equipped with a stirrer, a reflux condenser, and a stirrer was purged with nitrogen while 163 parts of the phenol resin of the present invention (P1 hydroxyl group equivalent 243 g / eq.), 433 parts of epichlorohydrin (7 molar equivalents to phenol resin) ), 130 parts of methanol was added, dissolved under stirring, and the temperature was raised to 70 to 75 ° C. Next, 30 parts of flaky sodium hydroxide was added in portions over 90 minutes, and the reaction was further carried out at 75 ° C. for 75 minutes.
- the phenol resin of the present invention P1 hydroxyl group equivalent 243 g / eq.
- epichlorohydrin 7 molar equivalents to phenol resin
- Example 1 shows the phenol resin (P1) or comparative phenol resin (P3) obtained in Example 1, epoxy resin (EP1 and EP2), filler (inorganic filler), wax, coupling agent, and curing accelerator. Were mixed at a ratio (equivalent) and uniformly mixed and kneaded using a mixing roll to obtain a curable resin composition.
- the curable resin composition was pulverized with a mixer and further tableted with a tablet machine.
- the tableted curable resin composition was transfer molded (175 ° C. ⁇ 60 seconds), and after demolding, was cured under the conditions of 160 ° C. ⁇ 2 hours + 180 ° C. ⁇ 6 hours to obtain a test piece for evaluation. Using this test specimen for evaluation, heat resistance and flame retardancy were measured and evaluated in the following manner. The test results are shown in Table 1.
- ⁇ Heat resistance test> Dynamic viscoelasticity measuring device: manufactured by TA-instruments, DMA-2980 Measurement temperature range: -30 ° C to 280 ° C Temperature rate: 2 ° C./min Test piece size: 5 mm ⁇ 50 mm cut out (thickness is about 800 ⁇ m).
- -Afterflame time Total afterflame time after 10 times of contact with a set of 5 samples.
- EP1 NC2000L manufactured by Nippon Kayaku Co., Ltd.
- EP2 Nippon Kayaku NC3000
- P3 Mirex XLC-3L manufactured by Mitsui Chemicals
- P2: P1 and P3 are mixed at a weight ratio of 33:67.
- P4: P1 and P3 are mixed at a weight ratio of 5:95.
- P5: P1 and P3 are mixed at a weight ratio of 10:90.
- Mixed wax Carnauba No. 1 curing accelerator: Triphenylphosphine (TPP manufactured by Hokuko Chemical Co., Ltd.)
- Coupling agent KBM-303 manufactured by Shin-Etsu Chemical Co., Ltd.
- Inorganic filler fused silica MSR-2122 manufactured by Kashimori Kogyo Co., Ltd. 83% by weight of resin Curing accelerator usage: The sample used for evaluation of heat resistance was 1% based on the weight of the epoxy resin, and the sample used for evaluation of flame retardancy was 2% based on the weight of the epoxy resin. Wax amount used: 0.3% by weight Composition coupling agent amount used: 0.4% by weight Filler epoxy resin / curing agent ratio: 1 equivalent
- the phenolic resin of the present invention can be used in an epoxy resin composition, and the cured product of the epoxy resin composition exhibits excellent heat resistance and flame retardancy. Therefore, various materials including semiconductor sealing materials and prepregs are used. It is useful when used for composite materials, adhesives, paints and the like.
Abstract
Description
すなわち本発明は、下記(1)~(7)に関する。 As a result of intensive studies to solve the above problems, the present inventors have completed the present invention.
That is, the present invention relates to the following (1) to (7).
R2の数を表し、0~4の整数であり、mはR1の数を表し、0~4の整数であり、Zは水素原子又は下記式(5)の構造を表し、複数存在するZのうち少なくとも一つは下記式(5)の構造を表す。) (In Formula (4), each R 1 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, a hydroxyl group, a nitro group, or Represents a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, and each R 2 independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, 6 to 6 carbon atoms, 10 represents a substituted or unsubstituted aryl group, a hydroxyl group, a nitro group, a formyl group, an allyl group, or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, k represents the number of R 2 , 0 Is an integer of ~ 4, m is the number of R 1 , is an integer of 0 to 4, Z is a hydrogen atom or a structure of the following formula (5), and at least one of a plurality of Z is Represents the structure of formula (5).)
(4)前項(1)又は前項(2)に記載のフェノール樹脂とエポキシ樹脂を含有してなるエポキシ樹脂組成物。
(5)半導体封止用途に用いられる前項(4)に記載のエポキシ樹脂組成物。
(6)前項(4)に記載のエポキシ樹脂組成物及びシート状の繊維基材からなるプリプレグ。
(7)前項(4)若しくは(5)に記載のエポキシ樹脂組成物、または前項(6)に記載のプリプレグを硬化してなる硬化物。 (3) An epoxy resin obtained by reacting the phenol resin according to (1) or (2) with epihalohydrin.
(4) An epoxy resin composition comprising the phenol resin and the epoxy resin according to (1) or (2).
(5) The epoxy resin composition according to (4), which is used for semiconductor encapsulation.
(6) A prepreg comprising the epoxy resin composition according to (4) above and a sheet-like fiber base material.
(7) A cured product obtained by curing the epoxy resin composition according to (4) or (5) or the prepreg according to (6).
フェノール化合物(a)は上記式(1)で表される化合物と上記式(2)で表される化合物との反応によって得られる。 First, the phenol compound (a) will be described.
The phenol compound (a) is obtained by a reaction between the compound represented by the above formula (1) and the compound represented by the above formula (2).
式(2)で表される化合物は式(1)で表される化合物1モルに対して1.0~1.05モルを使用する。 The phenol compound (a) is obtained by an aldol condensation reaction between one or more compounds represented by the formula (1) and a compound represented by the formula (2) under acidic conditions or basic conditions.
The compound represented by the formula (2) is used in an amount of 1.0 to 1.05 mol with respect to 1 mol of the compound represented by the formula (1).
上記式(3)で表される化合物は、例えば、HCA(三光株式会社製)として入手することができる。 The phenol resin (b) of the present invention can be obtained by subjecting the phenol compound (a) to an addition reaction with the phosphorus-containing compound represented by the above formula (3).
The compound represented by the above formula (3) can be obtained, for example, as HCA (manufactured by Sanko Co., Ltd.).
本発明のエポキシ樹脂は、上記手法によって得られた本発明のフェノール樹脂(b)とアルコール溶剤中、エピハロヒドリンとを反応させ、エポキシ化することにより得られる。なお、エポキシ化の際には、本発明のフェノール樹脂(b)の1種類のみを使用しても、2種以上を併用してもよい。また、本発明のフェノール樹脂(b)に、フェノール樹脂(b)以外のフェノール化合物を併用しても良い。
併用できるフェノール樹脂(b)以外のフェノール化合物としては、エポキシ樹脂の原料として通常用いられるフェノール化合物であれば特に制限なく用いることができる。
本発明のエポキシ樹脂としては、特に優れた溶剤溶解性を示し、なおかつ高い難燃性を有する硬化物が得られることから、式(2)で表される化合物と式(1)で表される化合物との反応によって得られたフェノール化合物(a)と、式(3)で表されるリン含有化合物と反応により得られた本発明のフェノール樹脂(b)のエポキシ化物が好ましい。 Next, the epoxy resin of this invention is demonstrated.
The epoxy resin of the present invention can be obtained by reacting the phenol resin (b) of the present invention obtained by the above method with an epihalohydrin in an alcohol solvent and epoxidizing it. In addition, in the case of epoxidation, only 1 type of the phenol resin (b) of this invention may be used, or 2 or more types may be used together. Moreover, you may use together phenolic compounds other than a phenol resin (b) with the phenol resin (b) of this invention.
As a phenol compound other than the phenol resin (b) that can be used in combination, any phenol compound that is usually used as a raw material for an epoxy resin can be used without particular limitation.
The epoxy resin of the present invention is represented by the compound represented by the formula (2) and the formula (1) because a cured product exhibiting particularly excellent solvent solubility and having high flame retardancy can be obtained. The epoxidized product of the phenol resin (b) of the present invention obtained by reacting the phenol compound (a) obtained by the reaction with the compound and the phosphorus-containing compound represented by the formula (3) is preferred.
エポキシ化反応に使用できるアルカリ金属水酸化物としては、水酸化ナトリウム、水酸化カリウム等が挙げられ、これらは固形物をそのまま使用しても、あるいはその水溶液を使用してもよい。水溶液を使用する場合は、該アルカリ金属水酸化物の水溶液を連続的に反応系内に添加すると共に、減圧下または常圧下で連続的に留出させた水及びエピハロヒドリンの混合液から分液により水を除去し、エピハロヒドリンのみを反応系内に連続的に戻す方法でもよい。アルカリ金属水酸化物の使用量は、本発明のフェノール樹脂(b)の水酸基1モルに対して通常0.9~3.0モル、好ましくは1.0~2.5モル、より好ましくは1.0~2.0モル、特に好ましくは1.0~1.3モルである。
また、本発明者等は、エポキシ化反応において、特にフレーク状の水酸化ナトリウムを用いることで、水溶液とした水酸化ナトリウムを使用するよりも得られるエポキシ樹脂に含まれるハロゲン量を顕著に低減させることが可能となることを知見するに至った。更にこのフレーク状の水酸化ナトリウムは、反応系内に分割添加されることが好ましい。分割添加を行なうことで、反応温度の急激な減少を防ぐことができ、これにより不純物である1,3-ハロヒドリン体やハロメチレン体の生成を防止することができる。 Alkali metal hydroxides can be used in the epoxidation reaction.
Examples of the alkali metal hydroxide that can be used for the epoxidation reaction include sodium hydroxide, potassium hydroxide, and the like, and these may be used as they are, or an aqueous solution thereof may be used. When using an aqueous solution, the aqueous solution of the alkali metal hydroxide is continuously added to the reaction system and separated from a mixture of water and epihalohydrin distilled continuously under reduced pressure or normal pressure. Alternatively, water may be removed and only the epihalohydrin is continuously returned to the reaction system. The amount of the alkali metal hydroxide used is usually 0.9 to 3.0 mol, preferably 1.0 to 2.5 mol, more preferably 1 with respect to 1 mol of the hydroxyl group of the phenol resin (b) of the present invention. The amount is from 0.0 to 2.0 mol, particularly preferably from 1.0 to 1.3 mol.
Further, the present inventors remarkably reduce the amount of halogen contained in the epoxy resin obtained by using flaky sodium hydroxide in the epoxidation reaction, rather than using sodium hydroxide as an aqueous solution. It came to know that it became possible. Further, the flaky sodium hydroxide is preferably added in portions in the reaction system. By performing divided addition, it is possible to prevent a rapid decrease in the reaction temperature, thereby preventing the formation of impurities such as 1,3-halohydrin and halomethylene.
反応終了後、反応物を水洗後、または水洗無しに加熱減圧下で反応液からエピハロヒドリンや溶媒等を除去する。また得られたエポキシ樹脂中に含まれるハロゲン量をさらに低減させるために、回収した本発明のエポキシ樹脂をトルエン、メチルイソブチルケトンなどの溶剤に溶解し、水酸化ナトリウム、水酸化カリウムなどのアルカリ金属水酸化物の水溶液を加えて反応を行ない、閉環を確実なものにすることも出来る。この場合、アルカリ金属水酸化物の使用量は、本発明のフェノール樹脂の水酸基1モルに対して通常0.01~0.3モル、好ましくは0.05~0.2モルである。反応温度は通常50~120℃、反応時間は通常0.5~2時間である。 The reaction temperature is usually 30 to 90 ° C, preferably 35 to 80 ° C. The reaction time is usually 0.5 to 10 hours, preferably 1 to 8 hours. In particular, when an alcohol solvent is used, it is preferably 50 ° C. to 90 ° C., more preferably 60 to 85 ° C., and particularly preferably 70 to 80 ° C.
After completion of the reaction, the reaction product is washed with water or without washing with water, and the epihalohydrin, the solvent and the like are removed from the reaction solution under heating and reduced pressure. In order to further reduce the amount of halogen contained in the obtained epoxy resin, the recovered epoxy resin of the present invention is dissolved in a solvent such as toluene or methyl isobutyl ketone, and an alkali metal such as sodium hydroxide or potassium hydroxide. The reaction can be carried out by adding an aqueous solution of hydroxide to ensure ring closure. In this case, the amount of the alkali metal hydroxide used is usually 0.01 to 0.3 mol, preferably 0.05 to 0.2 mol, relative to 1 mol of the hydroxyl group of the phenol resin of the present invention. The reaction temperature is usually 50 to 120 ° C., and the reaction time is usually 0.5 to 2 hours.
他のエポキシ樹脂を併用する場合、本発明のエポキシ樹脂組成物中の全エポキシ樹脂成分に占める本発明のエポキシ樹脂の割合は30質量%以上が好ましく、40質量%以上がより好ましく、70質量%以上が更に好ましく、特に好ましくは100質量%(他のエポキシ樹脂を併用しない場合)である。ただし、本発明のエポキシ樹脂をエポキシ樹脂組成物の改質剤として使用する場合は、全エポキシ樹脂中で1~30質量%となる割合で添加する。 Specific examples of other epoxy resins include bisphenols (bisphenol A, bisphenol F, bisphenol S, biphenol, bisphenol AD, bisphenol I, etc.) and phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted) Naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene and dihydroxynaphthalene) and various aldehydes (formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde, etc.) Of polycondensates with benzene, aromatic compounds such as xylene and formaldehyde Polycondensates of compounds and phenols, phenols and various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene and isoprene Etc.), polycondensates of phenols and ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.), phenols and aromatic dimethanols (benzene dimethanol, biphenyl dimethanol, etc.) Polycondensates, phenols and aromatic dichloromethyls (α, α'-dichloroxylene, bischloromethylbiphenyl, etc.), phenols and aromatic bisalkoxymethyls Polycondensates with bismethoxymethylbenzene, bismethoxymethylbiphenyl, bisphenoxymethylbiphenyl, etc., polycondensates of bisphenols and various aldehydes, and glycidyl ether epoxy resins obtained by glycidylation of alcohols, alicyclic An epoxy resin, a glycidylamine-based epoxy resin, a glycidyl ester-based epoxy resin, and the like can be mentioned, but the epoxy resin is not limited to these as long as it is a commonly used epoxy resin. These may be used alone or in combination of two or more.
When other epoxy resins are used in combination, the proportion of the epoxy resin of the present invention in the total epoxy resin component in the epoxy resin composition of the present invention is preferably 30% by mass or more, more preferably 40% by mass or more, and 70% by mass. The above is more preferable, and 100% by mass (when no other epoxy resin is used in combination) is particularly preferable. However, when the epoxy resin of the present invention is used as a modifier for the epoxy resin composition, it is added in a proportion of 1 to 30% by mass in the total epoxy resin.
(a)アミン系化合物 ジアミノジフェニルメタン、ジエチレントリアミン、トリエチレンテトラミン、ジアミノジフェニルスルホン、イソホロンジアミン及びナフタレンジアミン等
(b)酸無水物系化合物 無水フタル酸、無水トリメリット酸、無水ピロメリット酸、無水マレイン酸、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、無水メチルナジック酸、ヘキサヒドロ無水フタル酸及びメチルヘキサヒドロ無水フタル酸等
(c)アミド系化合物 ジシアンジアミド、若しくはリノレン酸の2量体とエチレンジアミンより合成されるポリアミド樹脂等、 When the epoxy resin composition of the present invention contains the epoxy resin of the present invention as an essential component, it is preferable to use a curing agent. In this case, the curing agent that can be used may be the above-described phenolic resin of the present invention or other curing agent. Examples of other curing agents include amine compounds, acid anhydride compounds, amide compounds, and phenol compounds. Specific examples of these other curing agents are shown in the following (a) to (e).
(A) Amine-based compounds diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, naphthalenediamine, etc. (b) acid anhydride-based compounds phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride , Tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl nadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, etc. (c) Amide compounds Dicyandiamide or linolenic acid dimer and ethylenediamine Polyamide resin, etc.
(e)その他 イミダゾール類、BF3 -アミン錯体、グアニジン誘導体 (D) Phenol compounds Polyhydric phenols (bisphenol A, bisphenol F, bisphenol S, fluorene bisphenol, terpene diphenol, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 3,3 ', 5, 5′-tetramethyl- (1,1′-biphenyl) -4,4′-diol, hydroquinone, resorcin, naphthalenediol, tris- (4-hydroxyphenyl) methane and 1,1,2,2-tetrakis (4 -Hydroxyphenyl) ethane, etc .; phenols (eg, phenol, alkyl-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene and dihydroxynaphthalene) and aldehydes (formaldehyde, acetaldehyde, benzaldehyde, p-hydro) A phenol resin obtained by condensation with xybenzaldehyde, o-hydroxybenzaldehyde, furfural, etc.), ketones (p-hydroxyacetophenone, o-hydroxyacetophenone, etc.), or dienes (dicyclopentadiene, tricyclopentadiene, etc.); Phenols and substituted biphenyls (such as 4,4′-bis (chloromethyl) -1,1′-biphenyl and 4,4′-bis (methoxymethyl) -1,1′-biphenyl), or substituted phenyls ( Phenol resins obtained by polycondensation with 1,4-bis (chloromethyl) benzene, 1,4-bis (methoxymethyl) benzene, 1,4-bis (hydroxymethyl) benzene, etc.); Or a modified product of the phenol resin; Lumpur A and halogenated phenols such as brominated phenol resin (e) Other imidazoles, BF 3 - amine complex, guanidine derivatives
他の硬化剤は単独で用いてもよく、複数を併用してもよい。 Among these other curing agents, active hydrogen such as amine compounds such as diaminodiphenylmethane, diaminodiphenylsulfone and naphthalenediamine, and condensates of catechol with aldehydes, ketones, dienes, substituted biphenyls or substituted phenyls. A curing agent having a structure in which groups are adjacent is preferable because it contributes to the arrangement of the epoxy resin.
Other curing agents may be used alone or in combination.
硬化促進剤の使用量は、エポキシ樹脂100重量部当たり、通常0.2~5.0重量部、好ましくは、0.2~4.0重量部である。 If necessary, a curing accelerator may be added to the epoxy resin composition of the present invention. Specific examples of the curing accelerator include phosphines such as triphenylphosphine and bis (methoxyphenyl) phenylphosphine, imidazoles such as 2-methylimidazole, 2-ethylimidazole, 2-ethylimidazole and 4-methylimidazole, Tertiary amines such as 2- (dimethylaminomethyl) phenol, trisdimethylaminomethylphenol, diazabicycloundecene, tetrabutylammonium salt, triisopropylmethylammonium salt, trimethyldecanylammonium salt, cetyltrimethylammonium salt, etc. Quaternary phosphonium salts such as quaternary ammonium salts, triphenylbenzyl phosphonium salts, triphenylethyl phosphonium salts, tetrabutyl phosphonium salts (the counter ions of quaternary salts are halogens) , Organic acid ions, hydroxide ions and the like are not particularly specified, but organic acid ions and hydroxide ions are particularly preferable.), Metal compounds such as tin octylate, etc. are exemplified.
The amount of the curing accelerator used is usually 0.2 to 5.0 parts by weight, preferably 0.2 to 4.0 parts by weight per 100 parts by weight of the epoxy resin.
本発明のエポキシ樹脂組成物は従来知られているのと同様の方法で容易にその硬化物とすることが出来る。例えば、本発明のエポキシ樹脂組成物の必須成分であるエポキシ樹脂、硬化剤及び無機充填材、並びに必要により硬化促進剤、配合剤、各種熱硬化性樹脂や各種熱可塑性樹脂等を、必要に応じて押出機、ニーダ又はロール等を用いて均一になるまで充分に混合して得られた本発明のエポキシ樹脂組成物を、溶融注型法あるいはトランスファー成型法やインジェクション成型法、圧縮成型法などによって成型し、更にその融点以上で2~10時間加熱することにより本発明のエポキシ樹脂組成物の硬化物を得ることが出来る。前述の方法でリードフレーム等に搭載された半導体素子を封止することにより、本発明のエポキシ樹脂組成物を半導体封止用途に用いることができる。 The epoxy resin composition of the present invention can be obtained by uniformly mixing the above-mentioned components, and preferred applications thereof include semiconductor encapsulants and printed wiring boards.
The epoxy resin composition of the present invention can be easily made into a cured product by the same method as conventionally known. For example, an epoxy resin that is an essential component of the epoxy resin composition of the present invention, a curing agent and an inorganic filler, and, if necessary, a curing accelerator, a compounding agent, various thermosetting resins and various thermoplastic resins, as necessary Then, the epoxy resin composition of the present invention obtained by thoroughly mixing until uniform using an extruder, kneader, roll, etc. is obtained by a melt casting method, a transfer molding method, an injection molding method, a compression molding method, or the like. The cured product of the epoxy resin composition of the present invention can be obtained by molding and further heating for 2 to 10 hours above the melting point. By sealing the semiconductor element mounted on the lead frame or the like by the above-described method, the epoxy resin composition of the present invention can be used for semiconductor sealing applications.
上記のようにして得られるワニスをガラス繊維、カーボン繊維、ポリエステル繊維、ポリアミド繊維、アルミナ繊維及び紙などの繊維基材に含浸させた後に加熱によって溶剤を除去すると共に、本発明のエポキシ樹脂組成物を半硬化状態とすることにより、本発明のプリプレグを得ることが出来る。尚、ここで言う「半硬化状態」とは、反応性の官能基であるエポキシ基が一部未反応で残っている状態を意味する。該プリプレグを熱プレス成型して硬化物を得ることが出来る。 Moreover, the epoxy resin composition of this invention can also be made into the varnish containing a solvent. The varnish includes, for example, a mixture containing the epoxy resin of the present invention or the phenol resin of the present invention in at least one of an epoxy resin and a curing agent, and optionally containing other components such as an inorganic filler. Xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, N, N′-dimethylformamide, N, N′-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, Glycol ethers such as dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, ethyl acetate, vinegar Butyl, methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, propylene glycol monomethyl ether acetate, esters such as dialkyl glutarate, dialkyl succinate, dialkyl adipate, cyclic esters such as γ-butyrolactone, petroleum ether It can be obtained by mixing with an organic solvent such as petroleum-based solvents such as petroleum naphtha, hydrogenated petroleum naphtha and solvent naphtha. The amount of the solvent is usually 10 to 95% by mass, preferably 15 to 85% by mass, based on the entire varnish.
The varnish obtained as described above is impregnated into a fiber substrate such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber and paper, and then the solvent is removed by heating, and the epoxy resin composition of the present invention By making a semi-cured state, the prepreg of the present invention can be obtained. Here, the “semi-cured state” means a state in which an epoxy group which is a reactive functional group partially remains unreacted. The prepreg can be hot press molded to obtain a cured product.
なお、水酸基当量、軟化点、は以下の条件で測定した。
・水酸基当量
JIS K-7236に記載された方法で測定し、単位はg/eq.である。
・軟化点
JIS K-7234に準拠した方法で測定し、単位は℃である。 EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples. In the synthesis examples, examples, and comparative examples, “part” means “part by mass”.
The hydroxyl group equivalent and softening point were measured under the following conditions.
Hydroxyl equivalent: Measured by the method described in JIS K-7236, the unit is g / eq. It is.
-Softening point Measured by a method according to JIS K-7234, the unit is ° C.
撹拌機、還流冷却管、撹拌装置を備えたフラスコに、4’-ヒドロキシアセトフェノン150部、バニリン167部およびエタノール221部を仕込み、溶解した。これに97質量%硫酸22部を添加後60℃ まで昇温し、この温度で10時間反応後、反応液を水1324部に注入し、晶析させた。結晶を濾別後、水662部で2回水洗し、その後真空乾燥し、黄色結晶のフェノール化合物(a)を282部得た。得られた結晶のDSC測定による吸熱ピーク温度は233℃であった。 (Synthesis Example 1)
A flask equipped with a stirrer, a reflux condenser, and a stirrer was charged with 150 parts of 4′-hydroxyacetophenone, 167 parts of vanillin and 221 parts of ethanol and dissolved. After adding 22 parts of 97% by mass sulfuric acid thereto, the temperature was raised to 60 ° C., and after reacting at this temperature for 10 hours, the reaction solution was poured into 1324 parts of water for crystallization. The crystals were separated by filtration, washed twice with 662 parts of water, and then vacuum-dried to obtain 282 parts of a yellow crystalline phenol compound (a). The endothermic peak temperature of the obtained crystal as measured by DSC was 233 ° C.
撹拌機、還流冷却管、撹拌装置を備えたフラスコに、窒素パージを施しながらHCA(三光株式会社製)178部、キシレン360部を加え、100℃に加熱した。そこにフェノール化合物(a)200部を1時間かけて分割添加し、その後130℃に昇温し、10時間加熱還流した。反応物にエタノール180部を加えた後、エバポレーターで溶媒を減圧留去し、本発明のフェノール樹脂(b)(P1)を320g得た。得られたフェノール樹脂(b)の水酸基当量は243g/eqであり、軟化点は135.8℃であった。 Example 1
178 parts of HCA (manufactured by Sanko Co., Ltd.) and 360 parts of xylene were added to a flask equipped with a stirrer, a reflux condenser and a stirrer while purging with nitrogen, and heated to 100 ° C. Thereto, 200 parts of the phenol compound (a) was dividedly added over 1 hour, then heated to 130 ° C. and heated to reflux for 10 hours. After adding 180 parts of ethanol to the reaction product, the solvent was distilled off under reduced pressure with an evaporator to obtain 320 g of the phenol resin (b) (P1) of the present invention. The obtained phenol resin (b) had a hydroxyl group equivalent of 243 g / eq and a softening point of 135.8 ° C.
撹拌機、還流冷却管、撹拌装置を備えたフラスコに、窒素パージを施しながら本発明のフェノール樹脂(P1 水酸基当量243g/eq.)163部、エピクロロヒドリン433部(7モル当量 対 フェノール樹脂)、メタノール130部を加え、撹拌下で溶解し、70~75℃にまで昇温した。次いでフレーク状の水酸化ナトリウム30部を90分かけて分割添加した後、更に75℃で75分反応を行った。反応終了後、水90部で水洗を行い、油層からロータリーエバポレーターを用いて減圧下、過剰のエピクロルヒドリン等の溶剤類を留去した。残留物にメチルイソブチルケトン380部を加え溶解し、75℃にまで昇温した。撹拌下で30重量%の水酸化ナトリウム水溶液11部を加え、1時間反応を行った後、油層の洗浄水が中性になるまで水洗を行った。得られた溶液をロータリーエバポレーターを用いて減圧下、メチルイソブチルケトン等を留去することで本発明のエポキシ樹脂(EP1)183部を得た。得られたエポキシ樹脂のエポキシ当量は304g/eq.であった。 (Example 2)
A flask equipped with a stirrer, a reflux condenser, and a stirrer was purged with nitrogen while 163 parts of the phenol resin of the present invention (P1 hydroxyl group equivalent 243 g / eq.), 433 parts of epichlorohydrin (7 molar equivalents to phenol resin) ), 130 parts of methanol was added, dissolved under stirring, and the temperature was raised to 70 to 75 ° C. Next, 30 parts of flaky sodium hydroxide was added in portions over 90 minutes, and the reaction was further carried out at 75 ° C. for 75 minutes. After completion of the reaction, water was washed with 90 parts of water, and excess solvents such as epichlorohydrin were distilled off from the oil layer under reduced pressure using a rotary evaporator. To the residue, 380 parts of methyl isobutyl ketone was added and dissolved, and the temperature was raised to 75 ° C. Under stirring, 11 parts of a 30% by weight aqueous sodium hydroxide solution was added and reacted for 1 hour, followed by washing with water until the washing water of the oil layer became neutral. The resulting solution was distilled off methyl isobutyl ketone and the like under reduced pressure using a rotary evaporator to obtain 183 parts of the epoxy resin (EP1) of the present invention. The epoxy equivalent of the obtained epoxy resin is 304 g / eq. Met.
実施例1で得られたフェノール樹脂(P1)ないし比較用のフェノール樹脂(P3)を、エポキシ樹脂(EP1及びEP2)、フィラー(無機充填材)、ワックス、カップリング剤、硬化促進剤を表1の割合(当量)で配合し、ミキシングロールを用いて均一に混合・混練し、硬化性樹脂組成物を得た。この硬化性樹脂組成物をミキサーにて粉砕し、更にタブレットマシーンにてタブレット化した。このタブレット化された硬化性樹脂組成物をトランスファー成型(175℃×60秒)し、更に脱型後160℃×2時間+180℃×6時間の条件で硬化し、評価用試験片を得た。この評価用試験片を用いて、耐熱性と難燃性を以下の要領で測定、評価した。試験結果を表1に示す。 (Examples 3 to 6, Comparative Example 1)
Table 1 shows the phenol resin (P1) or comparative phenol resin (P3) obtained in Example 1, epoxy resin (EP1 and EP2), filler (inorganic filler), wax, coupling agent, and curing accelerator. Were mixed at a ratio (equivalent) and uniformly mixed and kneaded using a mixing roll to obtain a curable resin composition. The curable resin composition was pulverized with a mixer and further tableted with a tablet machine. The tableted curable resin composition was transfer molded (175 ° C. × 60 seconds), and after demolding, was cured under the conditions of 160 ° C. × 2 hours + 180 ° C. × 6 hours to obtain a test piece for evaluation. Using this test specimen for evaluation, heat resistance and flame retardancy were measured and evaluated in the following manner. The test results are shown in Table 1.
動的粘弾性測定器:TA-instruments製、DMA-2980
測定温度範囲:-30℃~280℃
温速度:2℃/分
試験片サイズ:5mm×50mmに切り出した物を使用した(厚みは約800μm)。
解析条件Tg:DMA測定に於けるTanδのピーク点(tanδMAX)をTgとした。
<難燃性試験>
・難燃性の判定:UL94に準拠して行った。ただし、サンプルサイズは幅12.5mm×長さ150mmとし、厚さは0.8mmで試験を行った。
・残炎時間:5個1組のサンプルに10回接炎したあとの残炎時間の合計。 <Heat resistance test>
Dynamic viscoelasticity measuring device: manufactured by TA-instruments, DMA-2980
Measurement temperature range: -30 ° C to 280 ° C
Temperature rate: 2 ° C./min Test piece size: 5 mm × 50 mm cut out (thickness is about 800 μm).
Analysis condition Tg: Tanδ peak point (tanδMAX) in DMA measurement was defined as Tg.
<Flame retardance test>
-Determination of flame retardancy: performed in accordance with UL94. However, the test was conducted with a sample size of 12.5 mm wide × 150 mm long and a thickness of 0.8 mm.
-Afterflame time: Total afterflame time after 10 times of contact with a set of 5 samples.
EP2:日本化薬社製 NC3000
P3:三井化学社製 ミレックスXLC-3L
P2:P1とP3を重量比で33:67の割合になるように混合
P4:P1とP3を重量比で5:95の割合になるように混合
P5:P1とP3を重量比で10:90の割合になるように混合
ワックス:カルナバ1号
硬化促進剤:トリフェニルフォスフィン(北興化学社製 TPP)
カップリング剤:信越化学工業社製 KBM-303
無機充填材:溶融シリカ 瀧森工業社製 MSR-2122 対樹脂83wt%
硬化促進剤使用量:
耐熱性の評価に使用する試料ではエポキシ樹脂重量に対し1%とし、難燃性の評価に使用する試料ではエポキシ樹脂重量に対し2%とした。
ワックス使用量:0.3重量% 対組成物
カップリング剤使用量:0.4重量% 対フィラー
エポキシ樹脂・硬化剤比率:1等当量 EP1: NC2000L manufactured by Nippon Kayaku Co., Ltd.
EP2: Nippon Kayaku NC3000
P3: Mirex XLC-3L manufactured by Mitsui Chemicals
P2: P1 and P3 are mixed at a weight ratio of 33:67. P4: P1 and P3 are mixed at a weight ratio of 5:95. P5: P1 and P3 are mixed at a weight ratio of 10:90. Mixed wax: Carnauba No. 1 curing accelerator: Triphenylphosphine (TPP manufactured by Hokuko Chemical Co., Ltd.)
Coupling agent: KBM-303 manufactured by Shin-Etsu Chemical Co., Ltd.
Inorganic filler: fused silica MSR-2122 manufactured by Kashimori Kogyo Co., Ltd. 83% by weight of resin
Curing accelerator usage:
The sample used for evaluation of heat resistance was 1% based on the weight of the epoxy resin, and the sample used for evaluation of flame retardancy was 2% based on the weight of the epoxy resin.
Wax amount used: 0.3% by weight Composition coupling agent amount used: 0.4% by weight Filler epoxy resin / curing agent ratio: 1 equivalent
なお、本出願は、2013年10月9日付で出願された日本国特許出願(特願2013-211750)に基づいており、その全体が引用により援用される。また、ここに引用されるすべての参照は全体として取り込まれる。 Although the invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.
This application is based on a Japanese patent application filed on October 9, 2013 (Japanese Patent Application No. 2013-21750), which is incorporated by reference in its entirety. Also, all references cited herein are incorporated as a whole.
The phenolic resin of the present invention can be used in an epoxy resin composition, and the cured product of the epoxy resin composition exhibits excellent heat resistance and flame retardancy. Therefore, various materials including semiconductor sealing materials and prepregs are used. It is useful when used for composite materials, adhesives, paints and the like.
Claims (7)
- 下記式(1)で表されるフェノール化合物と、下記式(2)で表される化合物との反応によってフェノール化合物(a)を得た後、さらに下記式(3)で表されるリン含有化合物を反応させて得られるフェノール樹脂(b)。
- 下記式(4)で表されるフェノール樹脂。
- 請求項1又は請求項2に記載のフェノール樹脂にエピハロヒドリンを反応させて得られるエポキシ樹脂。 An epoxy resin obtained by reacting the phenol resin according to claim 1 or 2 with an epihalohydrin.
- 請求項1又は請求項2に記載のフェノール樹脂とエポキシ樹脂を含有してなるエポキシ樹脂組成物。 An epoxy resin composition comprising the phenol resin according to claim 1 or claim 2 and an epoxy resin.
- 半導体封止用途に用いられる請求項4に記載のエポキシ樹脂組成物。 The epoxy resin composition according to claim 4, which is used for semiconductor sealing applications.
- 請求項4に記載のエポキシ樹脂組成物及びシート状の繊維基材からなるプリプレグ。 A prepreg comprising the epoxy resin composition according to claim 4 and a sheet-like fiber base material.
- 請求項4若しくは請求項5に記載のエポキシ樹脂組成物、または請求項6に記載のプリプレグを硬化してなる硬化物。 A cured product obtained by curing the epoxy resin composition according to claim 4 or 5, or the prepreg according to claim 6.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020167002775A KR20160068728A (en) | 2013-10-09 | 2014-10-08 | Phenolic resin, epoxy resin, epoxy resin composition, prepreg and cured product of said epoxy resin composition or prepreg |
JP2015541604A JP6671958B2 (en) | 2013-10-09 | 2014-10-08 | Phenol resin, epoxy resin, epoxy resin composition, prepreg and cured product thereof |
CN201480055628.XA CN105612190B (en) | 2013-10-09 | 2014-10-08 | Phenol resin, epoxy resin, composition epoxy resin, prepreg and their solidfied material |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013211750 | 2013-10-09 | ||
JP2013-211750 | 2013-10-09 |
Publications (1)
Publication Number | Publication Date |
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WO2015053298A1 true WO2015053298A1 (en) | 2015-04-16 |
Family
ID=52813114
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2014/076877 WO2015053298A1 (en) | 2013-10-09 | 2014-10-08 | Phenolic resin, epoxy resin, epoxy resin composition, prepreg and cured product of said epoxy resin composition or prepreg |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP6671958B2 (en) |
KR (1) | KR20160068728A (en) |
CN (1) | CN105612190B (en) |
TW (1) | TW201527345A (en) |
WO (1) | WO2015053298A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116515119A (en) * | 2023-05-11 | 2023-08-01 | 南京工业大学 | All-bio-based aryl diamine flame retardant, and preparation method and application thereof |
Families Citing this family (1)
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CN114409896B (en) * | 2022-01-20 | 2023-10-24 | 南京工业大学 | Preparation method of non-isocyanate polyurethane |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11111760A (en) * | 1997-10-06 | 1999-04-23 | Tomoegawa Paper Co Ltd | Bonding agent for electronic parts and bonding tape for electronic parts |
JPH11124489A (en) * | 1997-10-22 | 1999-05-11 | Sumitomo Bakelite Co Ltd | Flame retardant resin composition, prepreg and laminate using the same |
JP2005146182A (en) * | 2003-11-18 | 2005-06-09 | Sekisui Chem Co Ltd | Ozone-decomposable novolac resin and resist composition |
WO2011093474A1 (en) * | 2010-01-29 | 2011-08-04 | 日本化薬株式会社 | Phenolic compound, epoxy resin, epoxy resin composition, prepreg, and cured product thereof |
JP2012012590A (en) * | 2010-05-31 | 2012-01-19 | Hitachi Chem Co Ltd | Phosphorus-containing curing agent, epoxy resin composition, prepreg, resin film with support, metal foil-clad laminate and multilayer printed wiring board |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11323162A (en) | 1998-03-19 | 1999-11-26 | Hitachi Ltd | Insulation composition |
JP2003137971A (en) | 2001-11-02 | 2003-05-14 | Shin Kobe Electric Mach Co Ltd | Epoxy resin composition, prepreg, laminate and printed wiring board |
JP3885664B2 (en) | 2002-06-03 | 2007-02-21 | 新神戸電機株式会社 | Prepreg, laminated board and printed wiring board |
CN100343302C (en) * | 2002-11-28 | 2007-10-17 | 日本化药株式会社 | Flame-retardant epoxy resin composition and cured product obtained therefrom |
JP5010112B2 (en) | 2004-07-26 | 2012-08-29 | 新神戸電機株式会社 | Manufacturing method of prepreg, manufacturing method of laminated board and printed wiring board |
CA2599153A1 (en) * | 2005-02-25 | 2006-08-31 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin, hardenable resin composition containing the same and use thereof |
KR101324535B1 (en) * | 2005-10-21 | 2013-11-01 | 니폰 가야꾸 가부시끼가이샤 | Epoxy resin, curable resin composition, and cured product thereof |
EP2578613B8 (en) * | 2010-05-31 | 2018-12-19 | Hitachi Chemical Company, Ltd. | Epoxy resin composition and pre-preg, support-provided resin film, metallic foil clad laminate plate and multilayer printed circuit board utilizing said composition |
-
2014
- 2014-10-08 CN CN201480055628.XA patent/CN105612190B/en not_active Expired - Fee Related
- 2014-10-08 WO PCT/JP2014/076877 patent/WO2015053298A1/en active Application Filing
- 2014-10-08 JP JP2015541604A patent/JP6671958B2/en not_active Expired - Fee Related
- 2014-10-08 KR KR1020167002775A patent/KR20160068728A/en not_active Application Discontinuation
- 2014-10-09 TW TW103135174A patent/TW201527345A/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11111760A (en) * | 1997-10-06 | 1999-04-23 | Tomoegawa Paper Co Ltd | Bonding agent for electronic parts and bonding tape for electronic parts |
JPH11124489A (en) * | 1997-10-22 | 1999-05-11 | Sumitomo Bakelite Co Ltd | Flame retardant resin composition, prepreg and laminate using the same |
JP2005146182A (en) * | 2003-11-18 | 2005-06-09 | Sekisui Chem Co Ltd | Ozone-decomposable novolac resin and resist composition |
WO2011093474A1 (en) * | 2010-01-29 | 2011-08-04 | 日本化薬株式会社 | Phenolic compound, epoxy resin, epoxy resin composition, prepreg, and cured product thereof |
JP2012012590A (en) * | 2010-05-31 | 2012-01-19 | Hitachi Chem Co Ltd | Phosphorus-containing curing agent, epoxy resin composition, prepreg, resin film with support, metal foil-clad laminate and multilayer printed wiring board |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116515119A (en) * | 2023-05-11 | 2023-08-01 | 南京工业大学 | All-bio-based aryl diamine flame retardant, and preparation method and application thereof |
CN116515119B (en) * | 2023-05-11 | 2023-12-15 | 南京工业大学 | All-bio-based aryl diamine flame retardant, and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
TW201527345A (en) | 2015-07-16 |
CN105612190A (en) | 2016-05-25 |
CN105612190B (en) | 2017-11-10 |
KR20160068728A (en) | 2016-06-15 |
JP6671958B2 (en) | 2020-03-25 |
JPWO2015053298A1 (en) | 2017-03-09 |
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