JP4259536B2 - フェノール樹脂の製造方法、およびエポキシ樹脂の製造方法 - Google Patents
フェノール樹脂の製造方法、およびエポキシ樹脂の製造方法 Download PDFInfo
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- JP4259536B2 JP4259536B2 JP2006090758A JP2006090758A JP4259536B2 JP 4259536 B2 JP4259536 B2 JP 4259536B2 JP 2006090758 A JP2006090758 A JP 2006090758A JP 2006090758 A JP2006090758 A JP 2006090758A JP 4259536 B2 JP4259536 B2 JP 4259536B2
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- Prior art keywords
- epoxy resin
- group
- phenol
- dihydroxynaphthalene
- resin
- Prior art date
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- 229920000647 polyepoxide Polymers 0.000 title claims description 156
- 239000003822 epoxy resin Substances 0.000 title claims description 155
- 239000005011 phenolic resin Substances 0.000 title claims description 90
- 238000004519 manufacturing process Methods 0.000 title claims description 46
- 239000000203 mixture Substances 0.000 claims description 67
- -1 hydroxy aromatic compound Chemical class 0.000 claims description 53
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 229920000412 polyarylene Polymers 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 20
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 18
- 230000018044 dehydration Effects 0.000 claims description 11
- 238000006297 dehydration reaction Methods 0.000 claims description 11
- 125000001033 ether group Chemical group 0.000 claims description 9
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical group C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 claims description 9
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 claims description 8
- 238000006482 condensation reaction Methods 0.000 claims description 7
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 6
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical group C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- UAVUNEWOYVVSEF-UHFFFAOYSA-N 3,5-dihydroxybiphenyl Chemical compound OC1=CC(O)=CC(C=2C=CC=CC=2)=C1 UAVUNEWOYVVSEF-UHFFFAOYSA-N 0.000 claims description 3
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 description 44
- 239000003063 flame retardant Substances 0.000 description 35
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 125000000732 arylene group Chemical group 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- 229920005989 resin Polymers 0.000 description 27
- 239000011347 resin Substances 0.000 description 27
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 26
- 229920003986 novolac Polymers 0.000 description 26
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 26
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 17
- 239000000463 material Substances 0.000 description 16
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- 239000002904 solvent Substances 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 15
- 239000004065 semiconductor Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 239000003566 sealing material Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000004957 naphthylene group Chemical group 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 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 8
- 238000005406 washing Methods 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 229920000877 Melamine resin Polymers 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000001588 bifunctional effect Effects 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 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
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 6
- 239000000347 magnesium hydroxide Substances 0.000 description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 4
- 0 CCC(C=CC*1)=C1C=CC Chemical compound CCC(C=CC*1)=C1C=CC 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 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
- 150000007973 cyanuric acids Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 4
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical class C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 4
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- NCIAGQNZQHYKGR-UHFFFAOYSA-N naphthalene-1,2,3-triol Chemical compound C1=CC=C2C(O)=C(O)C(O)=CC2=C1 NCIAGQNZQHYKGR-UHFFFAOYSA-N 0.000 description 3
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- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
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- 238000010533 azeotropic distillation Methods 0.000 description 2
- 229910000416 bismuth oxide Inorganic materials 0.000 description 2
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- 150000001639 boron compounds Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 229910000514 dolomite Inorganic materials 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- WLPKFQRBARNCNR-UHFFFAOYSA-N ethene 1,3,5-triazine-2,4,6-triamine Chemical compound C=C.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 WLPKFQRBARNCNR-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007706 flame test Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 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
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
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- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
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- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
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- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
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- 238000011084 recovery Methods 0.000 description 1
- 238000010125 resin casting Methods 0.000 description 1
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- 238000007650 screen-printing Methods 0.000 description 1
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- 230000035939 shock Effects 0.000 description 1
- 229910052710 silicon 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
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
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- Polyethers (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
一方、近年、上記したエレクトロニクス分野では、ダイオキシン問題を代表とする環境問題への対応が不可欠であり、添加系のハロゲン系難燃剤を使用することなく、樹脂自体に難燃効果を持たせた所謂ハロゲンフリーの難燃システムが要求されている。これに応える合成樹脂としては前記ポリフェニレンエーテルが良好である。しかし乍ら、前記した通り、かかるポリフェニレンエーテルは合成時に高分子量化してしまう為に、一般に材料への高流動性の要求が高いエレクトロニクス分野への適用は困難なものであった。かかる観点から、例えば高分子量のポリアリーレンエーテルを1官能性フェノールと反応させることにより低分子量化する方法(例えば、特許文献2参照。)が提案されている。
然し乍ら、このポリアリーレンエーテルの低分子量化法によって得られる変性ポリアリーレンエーテルは、ある程度の分子量低減化を実現でき、溶剤を併用するワニス組成物としては使用可能であるものの特に電子部品の封止材のように溶融成形する場合、成形温度(具体的には150〜200℃)で流動しないため、硬化時間が極めて遅く、実用的な硬化物は得られていないのが現状であった。
ここで一般式(2)中、R2はそれぞれ独立的に水素原子又は炭素原子数1〜4のアルキル基を、n又はmはそれぞれ0〜2の整数であって、n又はmの何れか一方は1以上の整数であり、R1は水素原子又は下記一般式(2−2)
(R2はそれぞれ独立的に水素原子又は炭素原子数1〜4のアルキル基を、pは1又は2の整数を表す。)を表す。但し、上記一般式(2)において全芳香核の総数は2〜8である。なお、上記一般式(2)においてナフタレン骨格への結合位置はナフタレン環を構成する2つの環の何れであってもよい。
ここで一般式(4)中、R1はそれぞれ独立的にメチル基または水素原子を、R2はそれぞれ独立的に水素原子又は炭素原子数1〜4のアルキル基を、n又はmはそれぞれ0〜2の整数であって、n又はmの何れか一方は1以上の整数であり、R1は水素原子又は下記一般式(4−2)
(R3はそれぞれ独立的にメチル基または水素原子を、R2はそれぞれ独立的に水素原子又は炭素原子数1〜4のアルキル基を、pは1又は2の整数を表す。)を表す。但し、上記一般式(4)において全芳香核の総数は2〜8である。なお、上記一般式(4)においてナフタレン骨格への結合位置はナフタレン環を構成する2つの環の何れであってもよい。
2)融点測定法:メトラー製DSC822e 昇温速度:3℃/分
3)GPC:
・装置:東ソー株式会社製 HLC−8220 GPC、カラム:東ソー株式会社製 TSK−GEL G2000HXL+G2000HXL+G3000HXL+G4000HXL
・溶媒:テトラヒドロフラン
・流速:1ml/min
・検出器:RI
4)MS :日本電子株式会社製 二重収束型質量分析装置 AX505H(FD505H)
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、下記式
更に2,7−ジヒドキシナフタレンが5分子間脱水して生成した2,7−ジヒドロキシナフタレン5量構造(Mw:728)に、トリメチルシリル基分の分子量(Mw:72)が3個(M+=945)、4個(M+=1018)付いたピークを確認した。
実施例1において、2,7−ジヒドロキシナフタレン160gを1,6−ジヒドロキシナフタレン160gに変更する以外は実施例1と同様にして、フェノール樹脂(a−2)147gを得た。得られたフェノール樹脂(a−2)は褐色固体であり、水酸基当量は135g/eq、融点は137℃であった。図5のGPCチャートより未反応の原料(1,6−ジヒドロキシナフタレン)の残存率はGPCによる面積比で24%であることを確認した。
実施例1において、2,7−ジヒドロキシナフタレン160gを2,7−ジヒドロキシナフタレン80g(0.5モル)と1,3−ジヒドロキシベンゼン55g(0.5モル)の混合物に変更する以外は実施例1と同様にして、フェノール樹脂(a−3)125gを得た。得られたフェノール樹脂(a−3)は褐色固体であり、水酸基当量は101g/eq、融点は136℃であった。図6のGPCチャートより未反応の原料(2,7−ジヒドロキシナフタレンと1,3−ジヒドロキシベンゼンの合計)の残存率はGPCによる面積比で36%であることを確認した。
実施例1において、2,7−ジヒドロキシナフタレン160gを1,3−ジヒドロキシベンゼン110g(1.0モル)に変更する以外は実施例1と同様にして、本発明のポリアリーレンエーテル化合物(a−4)100gを得た。得られたフェノール樹脂(a−4)は褐色固体であり、水酸基当量は85g/eq、融点は122℃であった。GPCチャートより未反応の原料(1,3−ジヒドロキシベンゼン)の残存モル率は36%であることを確認した。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、下記式
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに、窒素ガスパージを施しながら、実施例1で得られたフェノール樹脂(a−1)120g、エピクロルヒドリン463g(5.0モル)、n−ブタノール139g、テトラエチルベンジルアンモニウムクロライド2gを仕込み溶解させた。65℃に昇温した後、共沸する圧力まで減圧して、49%水酸化ナトリウム水溶液90g(1.1モル)を5時間かけて滴下した。その後、同条件で0.5時間撹拌を続けた。この間、共沸によって留出してきた留出分をディーンスタークトラップで分離し、水層を除去し、油層を反応系内に戻しながら、反応を行った。その後、未反応のエピクロルヒドリンを減圧蒸留によって留去させた。それで得られた粗エポキシ樹脂にメチルイソブチルケトン432gとn−ブタノール130gとを加え溶解した。更にこの溶液に10%水酸化ナトリウム水溶液10gを添加して80℃で2時間反応させた後に洗浄液のPHが中性となるまで水150gで水洗を3回繰り返した。次いで共沸によって系内を脱水し、精密濾過を経た後に、溶媒を減圧下で留去して、エポキシ樹脂170gを得た(以下、これを「エポキシ樹脂(b−1)」と略記する。)。得られたエポキシ樹脂(b−1)の150℃の溶融粘度は0.5dPa・s、エポキシ当量は187g/eqであった。
実施例1において、48%水酸化カリウム水溶液23g(0.2モル)をパラトルエンスルホン酸・1水和物2gに変更する以外は、実施例1と同様にして、比較用ポリアリーレンエーテル化合物(a’−1)145gを得た。得られたポリアリーレンエーテル化合物(a’−1)は褐色固体であり、水酸基当量は183g/eq、融点は測定できず、分解点は250℃であった。
エポキシ樹脂としてジャパンエポキシレジン株式会社製YX−4000H(テトラメチルビフェノール型エポキシ樹脂、エポキシ当量:195g/eq)、日本化薬株式会社製NC−3000(ビフェニルアラルキル型エポキシ樹脂、エポキシ当量:277g/eq)、大日本インキ化学工業株式会社製EPICLON N−665−EXP(クレゾールノボラック型エポキシ樹脂、エポキシ当量:203g/eq)、及び上記エポキシ樹脂(b−1)、硬化剤として上記フェノール樹脂a−1〜a−5、a’−1及び、三井化学製ミレックスXLC−3L(フェノールアラルキル樹脂 水酸基当量:172g/eq)を用い、硬化促進剤としてトリフェニルホスフィン(TPP)、難燃剤として縮合燐酸エステル(大八化学工業株式会社製PX−200)、水酸化マグネシウム(エア・ウォーター株式会社製エコーマグZ−10)、無機充填材として球状シリカ(株式会社マイクロン製S−COL)、シランカップリング剤としてγ−グリシドキシトリエトキシキシシラン(信越化学工業株式会社製KBM−403)、カルナウバワックス(株式会社セラリカ野田製PEARL WAX No.1−P)、カーボンブラックを用いて表1〜2に示した組成で配合し、2本ロールを用いて100℃の温度で10分間溶融混練して目的の組成物を得た。得られたエポキシ樹脂組成物について、下記手法によりゲルタイムを測定し、硬化性を試験した。また、これを180℃で10分間プレス成形し、その後180℃で5時間さらに硬化せしめた後に、UL−94試験法に準拠した厚さ1.6mmの試験片を作成し、下記方法により、硬化物の物性を確認した。
ガラス転移温度:粘弾性測定装置(レオメトリック社製 固体粘弾性測定装置RSAII、二重カレンチレバー法;周波数1Hz、昇温速度3℃/min)を用いて測定した。
Claims (12)
- フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)を、塩基性触媒(B)の存在下に脱水縮合反応させることを特徴とするポリアリーレンエーテル構造を有するフェノール樹脂の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、1,3−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、1,8−ジヒドロキシナフタレン、2,7−ジヒドロキシナフタレン、1,3−ジヒドロキシベンゼン、5−フェニル−1,3−ジヒドロキシベンゼン、及び1,3,6−トリヒドロキシベンゼンからなる群から選択されるものである請求項1記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシナフタレン類である請求項1又は2記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシベンゼン類である請求項1又は2記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシナフタレン類とジヒドロキシベンゼン類との混合物である請求項1記載の製造方法。
- 前記脱水縮合反応を、100〜300℃の温度条件下に行う請求項1〜5の何れか1つに記載の製造方法。
- フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)を、塩基性触媒(B)の存在下に脱水縮合反応させることを特徴とするポリアリーレンエーテル構造を有するフェノール樹脂を製造する工程と、
前記工程で得られたフェノール樹脂を、(メチル)エピハロヒドリンと反応させる工程と
を備えることを特徴とするポリアリーレンエーテル構造を有するエポキシ樹脂の製造方法。 - 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、1,3−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、1,8−ジヒドロキシナフタレン、2,7−ジヒドロキシナフタレン、1,3−ジヒドロキシベンゼン、5−フェニル−1,3−ジヒドロキシベンゼン、及び1,3,6−トリヒドロキシベンゼンからなる群から選択されるものである請求項7記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシナフタレン類である請求項7記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシベンゼン類である請求項7記載の製造方法。
- 前記フェノール性水酸基を1分子中に2つ以上有する多価ヒドロキシ芳香族化合物(A)が、ジヒドロキシナフタレン類とジヒドロキシベンゼン類との混合物である請求項7記載の製造方法。
- 前記脱水縮合反応を、100〜300℃の温度条件下に行う請求項7〜11の何れか1つに記載の製造方法。
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WO2014065422A1 (ja) | 2012-10-26 | 2014-05-01 | 三菱瓦斯化学株式会社 | ハロゲン化シアンの製造方法、シアン酸エステル化合物及びその製造方法、並びに樹脂組成物 |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
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JP6476558B2 (ja) * | 2014-03-07 | 2019-03-06 | Dic株式会社 | 酸基含有(メタ)アクリレート樹脂、酸基含有(メタ)アクリレート樹脂の製造方法、硬化性樹脂材料、その硬化物、及びレジスト材料 |
JP6476559B2 (ja) * | 2014-03-07 | 2019-03-06 | Dic株式会社 | 酸基含有(メタ)アクリレート樹脂、酸基含有(メタ)アクリレート樹脂の製造方法、硬化性樹脂材料、その硬化物、及びレジスト材料 |
JP6497125B2 (ja) * | 2015-02-25 | 2019-04-10 | Dic株式会社 | ポリアリーレンエーテル樹脂、ポリアリーレンエーテル樹脂の製造方法、硬化性樹脂材料、その硬化物、半導体封止材料、半導体装置、プリプレグ、プリント回路基板、ビルドアップフィルム、ビルドアップ基板 |
TW201819453A (zh) * | 2016-06-15 | 2018-06-01 | 日商迪愛生股份有限公司 | 抗蝕用樹脂組成物及抗蝕膜 |
WO2021079711A1 (ja) * | 2019-10-25 | 2021-04-29 | Dic株式会社 | 多官能フェノール樹脂、多官能エポキシ樹脂、それらを含む硬化性樹脂組成物及びその硬化物 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0467826A3 (en) * | 1990-06-26 | 1992-10-07 | Ciba-Geigy Ag | Linear polymers |
JP3374255B2 (ja) * | 1993-04-28 | 2003-02-04 | 新日鐵化学株式会社 | 新規エポキシ樹脂及びその製造方法並びにそれを用いたエポキシ樹脂組成物 |
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