JP2020183485A - Novel polymer compound and resin composition containing the compound - Google Patents
Novel polymer compound and resin composition containing the compound Download PDFInfo
- Publication number
- JP2020183485A JP2020183485A JP2019088456A JP2019088456A JP2020183485A JP 2020183485 A JP2020183485 A JP 2020183485A JP 2019088456 A JP2019088456 A JP 2019088456A JP 2019088456 A JP2019088456 A JP 2019088456A JP 2020183485 A JP2020183485 A JP 2020183485A
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- Prior art keywords
- polymer compound
- resin composition
- compound
- acid chloride
- present
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 229920000642 polymer Polymers 0.000 title claims abstract description 66
- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- -1 dicarboxylic acid chloride compound Chemical class 0.000 claims abstract description 29
- 239000000853 adhesive Substances 0.000 claims abstract description 16
- 230000001070 adhesive effect Effects 0.000 claims abstract description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 3
- 239000003999 initiator Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 8
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000011889 copper foil Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 229920000106 Liquid crystal polymer Polymers 0.000 description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 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 4
- 239000011521 glass Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 229920001230 polyarylate Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-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
- 0 CC(C)(C(CC1CC=C)=CC=C1OC)c(cc1)cc(CC=C)c1OC(*COc1c(CC=C)cc(C(C)(C)c(cc2CC=C)ccc2OC(*)=O)cc1)=O Chemical compound CC(C)(C(CC1CC=C)=CC=C1OC)c(cc1)cc(CC=C)c1OC(*COc1c(CC=C)cc(C(C)(C)c(cc2CC=C)ccc2OC(*)=O)cc1)=O 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VJMJYBVERHZATL-UHFFFAOYSA-N (2,4,6-trimethylbenzoyl)phosphonoyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)C(=O)C1=C(C)C=C(C)C=C1C VJMJYBVERHZATL-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 1
- SHULEACXTONYPS-UHFFFAOYSA-N (3-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 SHULEACXTONYPS-UHFFFAOYSA-N 0.000 description 1
- URBLVRAVOIVZFJ-UHFFFAOYSA-N (3-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 URBLVRAVOIVZFJ-UHFFFAOYSA-N 0.000 description 1
- NPENBPVOAXERED-UHFFFAOYSA-N (4-benzoylphenyl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 NPENBPVOAXERED-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- ZNCDSAZBKYUMAB-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)octane Chemical compound CCCCCCCC(OOC(C)(C)C)OOC(C)(C)C ZNCDSAZBKYUMAB-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- UOZNXGJVAWDLQK-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=CC2=O)=O)=C1C UOZNXGJVAWDLQK-UHFFFAOYSA-N 0.000 description 1
- FPZQYYXSOJSITC-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrrole-2,5-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=CC1=O FPZQYYXSOJSITC-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- CWJHMZONBMHMEI-UHFFFAOYSA-N 1-tert-butylperoxy-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1 CWJHMZONBMHMEI-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 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 class 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 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- QIXDHVDGPXBRRD-UHFFFAOYSA-N 2,3,5-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(C)=C(C)C1=O QIXDHVDGPXBRRD-UHFFFAOYSA-N 0.000 description 1
- BHKAWXZKFKVZLK-UHFFFAOYSA-N 2,3-ditert-butyl-6-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(C(C)(C)C)=C1O BHKAWXZKFKVZLK-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 description 1
- LNTGGPJSADTYSG-UHFFFAOYSA-N 2-(2-carbonochloridoylphenoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(Cl)=O LNTGGPJSADTYSG-UHFFFAOYSA-N 0.000 description 1
- GTZXSBQCNBNWPK-UHFFFAOYSA-N 2-(2-chloro-2-oxoethoxy)acetyl chloride Chemical compound ClC(=O)COCC(Cl)=O GTZXSBQCNBNWPK-UHFFFAOYSA-N 0.000 description 1
- MHDULSOPQSUKBQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C(N1C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MHDULSOPQSUKBQ-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- MRDMGGOYEBRLPD-UHFFFAOYSA-N 2-ethoxy-1-(2-ethoxyphenyl)ethanone Chemical compound CCOCC(=O)C1=CC=CC=C1OCC MRDMGGOYEBRLPD-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- QKTWWGYCVXCKOJ-UHFFFAOYSA-N 2-methoxy-1-(2-methoxyphenyl)-2-phenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1OC QKTWWGYCVXCKOJ-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- CGCRIQNPIBHVCQ-UHFFFAOYSA-N 2-methylidenebutanedioyl dichloride Chemical compound ClC(=O)CC(=C)C(Cl)=O CGCRIQNPIBHVCQ-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- PPQRFOFHENJYMN-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(C)=C1C1=CC(=O)NC1=O PPQRFOFHENJYMN-UHFFFAOYSA-N 0.000 description 1
- ZKKDYLHSRWLPSP-UHFFFAOYSA-N 3-chloro-1-phenylpyrrole-2,5-dione Chemical compound O=C1C(Cl)=CC(=O)N1C1=CC=CC=C1 ZKKDYLHSRWLPSP-UHFFFAOYSA-N 0.000 description 1
- QAVUFFJVZGZJMO-UHFFFAOYSA-N 3-methyl-1-phenylpyrrole-2,5-dione Chemical compound O=C1C(C)=CC(=O)N1C1=CC=CC=C1 QAVUFFJVZGZJMO-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 1
- ASOXKYGOZZTVHL-UHFFFAOYSA-N 4-[(4-carbonochloridoylphenyl)diazenyl]benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1N=NC1=CC=C(C(Cl)=O)C=C1 ASOXKYGOZZTVHL-UHFFFAOYSA-N 0.000 description 1
- IFQUPKAISSPFTE-UHFFFAOYSA-N 4-benzoylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=CC=C1 IFQUPKAISSPFTE-UHFFFAOYSA-N 0.000 description 1
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- FTDZECHQBVIHKZ-UHFFFAOYSA-N 5,5-dibromo-2-phenylcyclohexa-1,3-diene Chemical group C1=CC(Br)(Br)CC=C1C1=CC=CC=C1 FTDZECHQBVIHKZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- BEUGBYXJXMVRFO-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-phenylmethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CC=C1 BEUGBYXJXMVRFO-UHFFFAOYSA-N 0.000 description 1
- ANCHPZQGZBCDBK-UHFFFAOYSA-N [PH2](O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C Chemical compound [PH2](O)=O.C1(=CC=CC=C1)C=1C(=C(C(=O)[Li])C(=CC1C)C)C ANCHPZQGZBCDBK-UHFFFAOYSA-N 0.000 description 1
- WHTKZGCDQCGCFG-UHFFFAOYSA-N [diphenyl-(2-trimethylsilylphenyl)silyl]peroxy-diphenyl-(2-trimethylsilylphenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)OO[Si](C=1C(=CC=CC=1)[Si](C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 WHTKZGCDQCGCFG-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- FWICIOVOJVNAIJ-UHFFFAOYSA-N bis(ethenyl) benzene-1,3-dicarboxylate Chemical compound C=COC(=O)C1=CC=CC(C(=O)OC=C)=C1 FWICIOVOJVNAIJ-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HXTYZWJVMWWWDK-UHFFFAOYSA-N cyclohexane-1,4-dicarbonyl chloride Chemical compound ClC(=O)C1CCC(C(Cl)=O)CC1 HXTYZWJVMWWWDK-UHFFFAOYSA-N 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 239000004744 fabric Substances 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
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- PDSULNVJASBMLP-UHFFFAOYSA-N furan-2,5-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)O1 PDSULNVJASBMLP-UHFFFAOYSA-N 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- NZZGQZMNFCTNAM-UHFFFAOYSA-N naphthalene-2,6-dicarbonyl chloride Chemical compound C1=C(C(Cl)=O)C=CC2=CC(C(=O)Cl)=CC=C21 NZZGQZMNFCTNAM-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009774 resonance method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- KHILLYASAGTPOI-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-2-sulfonate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 KHILLYASAGTPOI-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XPEMYYBBHOILIJ-UHFFFAOYSA-N trimethyl(trimethylsilylperoxy)silane Chemical compound C[Si](C)(C)OO[Si](C)(C)C XPEMYYBBHOILIJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Adhesive Tapes (AREA)
- Polyesters Or Polycarbonates (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、トルエン等の一般的な有機溶剤に対する溶解性が高く、かつその有機溶剤溶液を用いることによりキャスト法で容易にフィルム形状とすることができる新規の高分子化合物又は末端変性高分子化合物、及びこれらの高分子化合物とラジカル開始剤を含み、その硬化物がフレキシビリティー、耐熱性、難燃性及び接着性に優れる樹脂組成物に関する。 The present invention is a novel polymer compound or end-modified polymer compound which is highly soluble in a general organic solvent such as toluene and can be easily formed into a film shape by a casting method by using the organic solvent solution. The present invention relates to a resin composition containing these polymer compounds and a radical initiator, the cured product thereof having excellent flexibility, heat resistance, flame retardancy and adhesiveness.
芳香族ポリエステル化合物は結晶性の高い所謂液晶ポリマー樹脂と、結晶性の低い所謂非晶性ポリアリレート樹脂に大別される。
融点が２７０℃を超える液晶ポリマーは、熱可塑性樹脂としては極めて高い耐熱性を有することから近年フレキシブルな基板の材料に用いられている。（特許文献１）しかしながら、加工の際に融点以上の温度が必要であるためその製造設備は極めて限定されており、またその周辺部材に過剰な熱負荷が掛かることも問題であった。
一方で、液晶ポリマーよりも融点の低い非晶性ポリアリレートは、液晶ポリマーよりも低い温度で加工することができるものの、溶剤溶解性が極めて低いことが問題であった。特許文献２には溶剤溶解性を改良した非晶性ポリアリレートが記載されているが、同文献のポリアリレートは熱可塑性樹脂であるためガラス転移温度以上では流動してしまい、２６０℃以上の半田リフロー温度に晒される電気・電子部品用途に用い得るものではなかった。非特許文献１には、ジアリルビスフェノールＡとビスフェノールＡをイソフタル酸クロライドにより共重合した高分子が記載されている。この高分子化合物はアリル基を有するため光や熱ラジカル開始剤により架橋・熱硬化することが可能であるが、塩化メチレン、１，４−ジオキサン又はシクロヘキサノンといった毒性の高い溶剤にしか溶解せず、一般的なトルエンやケトン系溶剤には溶解しないことが記載されている。
Aromatic polyester compounds are roughly classified into so-called liquid crystal polymer resins having high crystallinity and so-called amorphous polyarylate resins having low crystallinity.
A liquid crystal polymer having a melting point of more than 270 ° C. has been used as a material for a flexible substrate in recent years because it has extremely high heat resistance as a thermoplastic resin. (Patent Document 1) However, since a temperature higher than the melting point is required during processing, the manufacturing equipment thereof is extremely limited, and there is also a problem that an excessive heat load is applied to the peripheral members thereof.
On the other hand, amorphous polyarylate, which has a lower melting point than the liquid crystal polymer, can be processed at a temperature lower than that of the liquid crystal polymer, but has a problem of extremely low solvent solubility. Patent Document 2 describes an amorphous polyarylate having improved solvent solubility, but since the polyarylate in the same document is a thermoplastic resin, it flows at a glass transition temperature or higher and is soldered at 260 ° C. or higher. It could not be used for electrical and electronic parts exposed to reflow temperature. Non-Patent Document 1 describes a polymer obtained by copolymerizing diallyl bisphenol A and bisphenol A with isophthalic acid chloride. Since this polymer compound has an allyl group, it can be crosslinked and thermally cured by light or a thermal radical initiator, but it is only soluble in highly toxic solvents such as methylene chloride, 1,4-dioxane or cyclohexanone. It is stated that it does not dissolve in general toluene or ketone solvents.
本発明は、上記の点に鑑みてなされたものであり、トルエンやケトンといった一般的な溶剤に可溶で優れたフィルム形成能を有すると共に、加熱による効果が可能であり、かつその硬化物が耐熱性、難燃性及び、接着性に優れる高分子化合物を提供することを目的とするものである。 The present invention has been made in view of the above points, is soluble in general solvents such as toluene and ketones, has an excellent film-forming ability, can be effective by heating, and has a cured product thereof. It is an object of the present invention to provide a polymer compound having excellent heat resistance, flame retardancy and adhesiveness.
本発明者らは鋭意検討を行った結果、特定構造の高分子化合物又は末端変性高分子化合物が上記の課題を解決することを見出し、本発明を完成させた。
即ち本発明は、
（１）下記式（１）
As a result of diligent studies, the present inventors have found that a polymer compound having a specific structure or a terminal-modified polymer compound solves the above-mentioned problems, and have completed the present invention.
That is, the present invention
(1) The following formula (1)
（式中、Ｘはジカルボン酸クロリド化合物からカルボン酸クロリド基を二つ除いた二価の連結基を表す。ｎは繰り返し単位数の平均値であって１乃至１００の範囲にある実数を表す。）で表される高分子化合物、
（２）前項（１）に記載の式（１）で表される高分子化合物とモノカルボン酸クロリド化合物との脱塩酸反応物である末端変性高分子化合物であって、下記式（２）
(In the formula, X represents a divalent linking group obtained by removing two carboxylic acid chloride groups from the dicarboxylic acid chloride compound. N represents an average value of the number of repeating units and represents a real number in the range of 1 to 100. ), A polymer compound,
(2) A terminal-modified polymer compound which is a dehydrochloric acid reaction product of a polymer compound represented by the formula (1) described in the previous item (1) and a monocarboxylic acid chloride compound, and has the following formula (2).
（式中、Ｘ及びｎは前項（１）に記載の式（１）におけるＸ及びｎと同じ意味を表す。Ｒはモノカルボン酸クロリド化合物からカルボン酸クロリド基を除いた残基を表す。）で表される末端変性高分子化合物、
（３）前項（１）に記載の高分子化合物又は請求項２に記載の末端変性高分子化合物、及びラジカル開始剤を含む樹脂組成物、
（４）更にラジカル重合性の化合物を含む前項（３）に記載の樹脂組成物、
（５）ラジカル重合性の化合物が、マレイミド化合物である前項（４）に記載の樹脂組成物、
（６）更に有機溶剤を含む前項（３）乃至（５）のいずれか一項に記載の樹脂組成物、
（７）前項（３）乃至（６）のいずれか一項に記載の樹脂組成物からなるフィルム状接着剤、及び
（８）前項（３）乃至（６）のいずれか一項に記載の樹脂組成物、又は前項（７）に記載のフィルム状接着剤の硬化物、
に関する。
(In the formula, X and n have the same meanings as X and n in the formula (1) described in the previous section (1). R represents a residue obtained by removing the carboxylic acid chloride group from the monocarboxylic acid chloride compound.) End-modified polymer compound represented by,
(3) A resin composition containing the polymer compound according to (1) above or the terminal-modified polymer compound according to claim 2 and a radical initiator.
(4) The resin composition according to (3) above, which further contains a radically polymerizable compound.
(5) The resin composition according to (4) above, wherein the radically polymerizable compound is a maleimide compound.
(6) The resin composition according to any one of (3) to (5) above, which further contains an organic solvent.
(7) A film-like adhesive comprising the resin composition according to any one of the preceding items (3) to (6), and (8) the resin according to any one of the preceding items (3) to (6). The composition, or the cured product of the film-like adhesive according to (7) above.
Regarding.
本発明によれば、トルエン等の一般的な有機溶剤に対する溶解性が高く、かつその有機溶剤溶液を用いることによりキャスト法で容易にフィルム形状とすることが可能であり、ラジカル開始剤を併用した樹脂組成物の硬化物はフレキシビリティー、耐熱性、難燃性及び接着性等の特性に優れる高分子化合物及び末端変性高分子化合物を提供することができる。 According to the present invention, the film has high solubility in a general organic solvent such as toluene, and can be easily formed into a film shape by a casting method by using the organic solvent solution, and a radical initiator is used in combination. As the cured product of the resin composition, it is possible to provide a polymer compound having excellent properties such as flexibility, heat resistance, flame retardancy and adhesiveness, and a terminal-modified polymer compound.
以下に、本発明の実施形態について説明する。
本発明の高分子化合物はジアリルビスフェノールＡとジカルボン酸クロリド化合物を脱塩酸反応させることにより得ることができる。
Hereinafter, embodiments of the present invention will be described.
The polymer compound of the present invention can be obtained by dehydrochlorinating a diallyl bisphenol A and a dicarboxylic acid chloride compound.
本高分子化合物の原料であるジアリルビスフェノールＡとしては市販のものが使用できる。具体的な商品名としては小西化学株式会社製のＢＰＡ−ＣＡが挙げられる。 As the raw material of the present polymer compound, diallyl bisphenol A, a commercially available product can be used. Specific product names include BPA-CA manufactured by Konishi Chemical Industry Co., Ltd.
本発明の高分子化合物の原料であるジカルボン酸クロリド化合物の具体例としてはフタル酸ジクロリド、グルタリルクロリド、イソフタル酸ジクロリド、テレフタル酸ジクロリド、塩化オキサリル、マロニルクロリド、アジポイルクロリド、アゼラオイルクロリド、セバコイルクロリド、アゾベンゼン−４，４’−ジカルボニルジクロリド、４，４’−ビフェニルジカルボニルクロリド、イタコン酸クロリド、ヘキサハイドロテレフタル酸ジクロリド、２，６−ナフタレンジカルボン酸クロリド、４，４’−オキシジベンゾイルクロリド、２，５−フランジカルボニルジクロリド及びジグリコリルクロリド等が挙げられるが、テレフタル酸ジクロリド又はイソフタル酸ジクロリドが好ましい。 Specific examples of the dicarboxylic acid chloride compound which is the raw material of the polymer compound of the present invention include phthalic acid dichloride, glutalyl chloride, isophthalic acid dichloride, terephthalic acid dichloride, oxalyl chloride, malonyl chloride, adipoyl chloride, and azela oil chloride. , Sevacoyl chloride, azobenzene-4,4'-dicarbonyldichloride, 4,4'-biphenyldicarbonylchloride, itaconic acid chloride, hexahydroterephthalic acid dichloride, 2,6-naphthalenedicarboxylic acid chloride, 4,4'- Examples thereof include oxydibenzoyl chloride, 2,5-furandicarbonyldichloride and diglycolyl chloride, but terephthalic acid dichloride or isophthalic acid dichloride is preferable.
本発明の高分子化合物は、ジアリルビスフェノールＡを有機溶剤中に均一に溶解した後に、ジカルボン酸クロリド化合物を加えて加熱下で反応させることにより合成することができる。合成の際に用いられる有機溶剤の種類としては、トルエン、キシレン、メチルイソブチルケトン、シクロペンタノン、シクロヘキサノン、Ｎ−メチルピロリドン、ジメチルホルムアミド及びジメチルアセトアミド等が挙げられ、これらの混合溶剤でも構わないが、特に沸点が低く乾燥しやすいトルエンが特に好ましい。反応温度は通常５０乃至１５０℃であり、好ましくは６０乃至１４０℃である。反応時間は好ましくは１乃至６０時間である。 The polymer compound of the present invention can be synthesized by uniformly dissolving diallyl bisphenol A in an organic solvent, then adding a dicarboxylic acid chloride compound and reacting under heating. Examples of the type of organic solvent used in the synthesis include toluene, xylene, methyl isobutyl ketone, cyclopentanone, cyclohexanone, N-methylpyrrolidone, dimethylformamide, dimethylacetamide and the like, and a mixed solvent thereof may be used. In particular, toluene having a low boiling point and easy drying is particularly preferable. The reaction temperature is usually 50 to 150 ° C, preferably 60 to 140 ° C. The reaction time is preferably 1 to 60 hours.
反応を促進させるために触媒を使用することもできる。触媒としてはトリエチルアミン、トリプロペニルアミン及びピリジンなどの有機塩基化合物が好ましい。有機塩基化合物を触媒として使用する場合、反応によって生じる塩酸と有機塩基化合物が塩を形成するため、塩酸による反応装置の腐食を引き起こすことなく安全に反応を行うことができる。生成した塩は反応終了後、濾過によって容易に除去することができる。また反応後系中に残存する過剰の有機塩基化合物は、加熱減圧下、もしくは加熱下で窒素などのガスを系中に吹き込むことによって、溶剤と一緒に留去することができる。有機塩基化合物の使用量は発生する塩酸のモル数以上が好ましい。 A catalyst can also be used to accelerate the reaction. As the catalyst, organic base compounds such as triethylamine, tripropenylamine and pyridine are preferable. When an organic base compound is used as a catalyst, the hydrochloric acid generated by the reaction and the organic base compound form a salt, so that the reaction can be safely carried out without causing corrosion of the reaction apparatus by hydrochloric acid. The produced salt can be easily removed by filtration after the reaction is completed. Further, the excess organic base compound remaining in the system after the reaction can be distilled off together with the solvent by blowing a gas such as nitrogen into the system under heating and reduced pressure or under heating. The amount of the organic base compound used is preferably at least the number of moles of hydrochloric acid generated.
また、合成反応の際のアリル基同士の重合反応を防ぐために、重合禁止剤を反応前に加えておくことが好ましい。重合禁止剤の具体例としては、パラメトキシフェノール、メチルハイドロキノン、４−ｔ−ブチルピロカテコール、ｔ−ブチルヒドロキノン、１，４−ベンゾキノン、６−ｔ−ブチル−２，４−キシレノール、２，６−ジ−ｔ−ブチル−ｐ−クレゾール、２，６−ジ−ｔ−ブチル−ｐ−フェノール及びフェノチアジン等が挙げられる。 Further, in order to prevent the polymerization reaction between allyl groups during the synthesis reaction, it is preferable to add a polymerization inhibitor before the reaction. Specific examples of the polymerization inhibitor include paramethoxyphenol, methylhydroquinone, 4-t-butylpyrocatechol, t-butylhydroquinone, 1,4-benzoquinone, 6-t-butyl-2,4-xylenol, 2,6. Examples thereof include -di-t-butyl-p-cresol, 2,6-di-t-butyl-p-phenol and phenothiazine.
本発明の式（２）で表される末端変性高分子化合物は、本発明の式（１）で表される高分子化合物の末端をモノカルボン酸クロリド化合物で変性した化合物であり、ここで言う変性とは、式（１）で表される高分子化合物が末端に有するフェノール性水酸基と、モノカルボン酸クロリド化合物が有するカルボン酸クロリド基との脱塩酸反応（エステル化反応）を意味する。
本発明の末端変性高分子化合物は、式（１）で表される高分子化合物の両末端が変性された化合物（即ち、式（２）中のＡが−ＣＯＲ基の化合物）であっても一方の末端のみが変性された化合物（即ち、式（２）中のＡが水素原子の化合物）であっても構わないが、両末端が編成された末端変性高分子化合物が好ましい。末端に存在するフェノール性水酸基をエステル化反応により消失させることによって、ラジカル開始剤と組み合わせた樹脂組成物（後述する）の硬化物の誘電特性が更に向上する。
The terminal-modified polymer compound represented by the formula (2) of the present invention is a compound in which the terminal of the polymer compound represented by the formula (1) of the present invention is modified with a monocarboxylic acid chloride compound, and is referred to herein. The denaturation means a dehydroxation reaction (esterification reaction) of a phenolic hydroxyl group having a terminal of a polymer compound represented by the formula (1) and a carboxylic acid chloride group of a monocarboxylic acid chloride compound.
The terminal-modified polymer compound of the present invention may be a compound in which both ends of the polymer compound represented by the formula (1) are modified (that is, a compound in which A in the formula (2) is a -COR group). A compound in which only one end is modified (that is, a compound in which A in the formula (2) is a hydrogen atom) may be used, but a terminal-modified polymer compound in which both ends are knitted is preferable. By eliminating the phenolic hydroxyl group present at the terminal by the esterification reaction, the dielectric property of the cured product of the resin composition (described later) combined with the radical initiator is further improved.
モノカルボン酸クロリド基を有する化合物としてはメタクリル酸クロリド、アクリル酸クロリド、塩化ベンゾイル、フェニル酢酸クロリドが挙げられる。 Examples of the compound having a monocarboxylic acid chloride group include methacrylic acid chloride, acrylic acid chloride, benzoyl chloride, and phenylacetic acid chloride.
本発明の末端変性高分子化合物の製造方法としては、式（１）で表される高分子化合物とモノカルボン酸ジクロリド化合物を溶剤に溶解した後、モノカルボン酸ジクロリド化合物のモル数以上の有機塩基化合物（上記参照）を加えて脱塩酸反応を行う方法が挙げられ、本発明の高分子化合物の合成反応によって得られた溶液に、モノカルボン酸ジクロリド化合物及び有機塩基化合物を加えて末端変性高分子化合物を合成してもよく、反応条件は、上記した高分子化合物の反応条件と同様でよい。
モノカルボン酸ジクロリド化合物の添加量は、通常式（１）で表される高分子化合物と当モル以上であり、好ましくは式（１）で表される高分子化合物の２倍モル以上である。エステル化反応により生成した塩を濾過することにより、本発明の末端変性高分子化合物を得ることが出来る。また、反応後残存する有機塩基化合物及び未反応のモノカルボン酸ジクロリド化合物は、加熱減圧下、或いは加熱下で窒素等のガスを系中に吹きこむことにより、留去することができる。
As a method for producing the terminally modified polymer compound of the present invention, after dissolving the polymer compound represented by the formula (1) and the monocarboxylic acid dichloride compound in a solvent, an organic base having a number of moles or more of the monocarboxylic acid dichloride compound is used. A method of adding a compound (see above) to carry out a dehydroxylation reaction can be mentioned. A terminal-modified polymer is obtained by adding a monocarboxylic acid dichloride compound and an organic base compound to a solution obtained by a synthetic reaction of the polymer compound of the present invention. The compound may be synthesized, and the reaction conditions may be the same as those of the above-mentioned polymer compound.
The amount of the monocarboxylic acid dichloride compound added is usually equal to or more than the molar amount of the polymer compound represented by the formula (1), and preferably more than twice the molar amount of the polymer compound represented by the formula (1). The terminal-modified polymer compound of the present invention can be obtained by filtering the salt produced by the esterification reaction. Further, the organic base compound remaining after the reaction and the unreacted monocarboxylic acid dichloride compound can be distilled off by blowing a gas such as nitrogen into the system under heating and reduced pressure or under heating.
こうして得られた本発明の高分子化合物及び末端変性高分子化合物の分子量は、ＧＰＣの測定結果に基づいてポリスチレン換算で算出した重量平均分子量が、１，０００乃至２００，０００であることが好ましく、１，５００乃至１５０，０００であることがより好ましい。前記の範囲よりも分子量が小さい場合はフィルム形成能が不十分なことがあり、大きい場合は粘度が高くなり塗工等が困難となることがある。 The molecular weights of the polymer compound and the terminal-modified polymer compound of the present invention thus obtained are preferably such that the weight average molecular weight calculated in terms of polystyrene based on the measurement result of GPC is 1,000 to 200,000. More preferably, it is 1,500 to 150,000. If the molecular weight is smaller than the above range, the film forming ability may be insufficient, and if it is large, the viscosity may be high and coating or the like may be difficult.
本発明の樹脂組成物は、ラジカル開始剤を含有する。本発明の樹脂組成物におけるラジカル開始剤の含有量は、本発明の樹脂組成物の全固形分（有機溶剤以外の樹脂組成物の全ての成分）中に通常０．１乃至１０質量％、好ましくは０．１乃至８質量％である。 The resin composition of the present invention contains a radical initiator. The content of the radical initiator in the resin composition of the present invention is usually 0.1 to 10% by mass, preferably 0.1 to 10% by mass, based on the total solid content of the resin composition of the present invention (all components of the resin composition other than the organic solvent). Is 0.1 to 8% by mass.
本発明の樹脂組成物が含有するラジカル開始剤は、熱ラジカル開始剤及び光ラジカル開始剤の何れでもよい。
熱ラジカル開始剤の具体例としては、ベンゾイルパーオキサイド、クメンハイドロパーオキサイド、２，５−ジメチルヘキサン−２，５−ジハイドロパーオキサイド、２，５−ジメチル−２，５−ジ（ｔ−ブチルパーオキシ）ヘキシン−３、ジ−ｔ−ブチルパーオキサイド、ｔ−ブチルクミルパーオキサイド、α，α−ビス（ｔ−ブチルパーオキシ−ｍ−イソプロピル）ベンゼン、２，５−ジメチル−２，５−ジ（ｔ−ブチルパーオキシ）ヘキサン、ジクミルパーオキサイド、ジ−ｔ−ブチルパーオキシイソフタレート、ｔ−ブチルパーオキシベンゾエート、２，２−ビス（ｔ−ブチルパーオキシ）ブタン、２，２−ビス（ｔ−ブチルパーオキシ）オクタン、２，５−ジメチル−２，５−ジ（ベンゾイルパーオキシ）ヘキサン、ジ（トリメチルシリル）パーオキサイド及びトリメチルシリルトリフェニルシリルパーオキサイド等の過酸化物が挙げられる。
The radical initiator contained in the resin composition of the present invention may be either a thermal radical initiator or a photoradical initiator.
Specific examples of the thermal radical initiator include benzoyl peroxide, cumene hydroperoxide, 2,5-dimethylhexane-2,5-dihydroperoxide, and 2,5-dimethyl-2,5-di (t-butyl). Peroxy) hexin-3, di-t-butyl peroxide, t-butylcumyl peroxide, α, α-bis (t-butylperoxy-m-isopropyl) benzene, 2,5-dimethyl-2,5- Di (t-butylperoxy) hexane, dicumyl peroxide, di-t-butylperoxyisophthalate, t-butylperoxybenzoate, 2,2-bis (t-butylperoxy) butane, 2,2- Peroxides such as bis (t-butylperoxy) octane, 2,5-dimethyl-2,5-di (benzoylperoxy) hexane, di (trimethylsilyl) peroxide and trimethylsilyltriphenylsilyl peroxide can be mentioned.
光ラジカル開始剤の具体例としては、アセトフェノン、３−ヒドロキシアセトフェノン、アントラキノン、アントラキノン−２−スルホン酸ナトリウム一水和物、ｐ−アニシル、ベンジル、ベンゾイン、ベンゾフェノン、２−ベンゾイル安息香酸、４，４’−ビス（ジエチルアミノ）ベンゾフェノン、ベンゾインメチルエーテル、３，３’，４，４’−べンゾフェノンテトラカルボン酸二無水物、ベンゾインイソブチルエーテル、ベンゾインエチルエーテル、ベンゾイルギ酸エステル、４−ベンゾイル安息香酸、２，２’−ビス（２−クロロフェニル）−４，４’，５，５’−テトラフェニル−１，２’−ビイミダゾール、２−ベンゾイル安息香酸メチル、２−（１，３−ベンゾジオキソール−５−イル）−４，６−ビス（トリクロロメチル）−１，３，５−トリアジン、２，３−ボルナンジオン、２−クロロチオキサントン、フェロセン、４，４’−ジヒドロキシベンゾフェノン、４，４’−ジクロロベンゾフェノン、２，２’−ジエトキシアセトフェノン、２，２’−ジメトキシ−２−フェニルアセトフェノン、ジベンゾスベレノン、２，４−ジエチルチオキサンテン−９−オン、４−（ジメチルアミノ）ベンゾフェノン、ジフェニル（２，４，６−トリメチルベンゾイル）ホスフィンオキシド、１，４−ジベンゾイルベンゼン、４’−ヒドロキシアセトフェノン、４−ヒドロキシベンゾフェノン、１−ヒドロキシシクロへキシルフェニルケトン、２−ヒドロキシ−２−メチルプロピオフェノン、２−ヒドロキシ−４’−（２−ヒドロキシエトキシ）−２−メチルプロピオフェノン、３−ヒドロキシベンゾフェノン、２−イソプロピルチオキサントン、フェニル（２，４，６−トリメチルベンゾイル）ホスフィン酸リチウム、２−メチルベンゾフェノン、３−メチルベンゾフェノン、２−メチル―４’−（メチルチオ）−２−モルホリノプロピオフェノン、９，１０−フェナントレンキノン、２−フェニル−２−（ｐ−トルエンスルホニルオキシ）アセトフェノン及びフェニルビス（２，４，６−トリメチルベンゾイル）ホスフィンオキシド等が挙げられる。 Specific examples of the photoradical initiator include acetophenone, 3-hydroxyacetophenone, anthraquinone, anthraquinone-2-sulfonate sodium monohydrate, p-anisyl, benzyl, benzophenone, benzophenone, 2-benzoylbenzoic acid, 4,4. '-Bis (diethylamino) benzophenone, benzoin methyl ether, 3,3', 4,4'-benzophenone tetracarboxylic dianhydride, benzoin isobutyl ether, benzoin ethyl ether, benzoyl silicate, 4-benzoyl benzoic acid , 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenyl-1,2'-biimidazole, methyl 2-benzoylbenzoate, 2- (1,3-benzodio) Xol-5-yl) -4,6-bis (trichloromethyl) -1,3,5-triazine, 2,3-bornandione, 2-chlorothioxanthone, ferrocene, 4,4'-dihydroxybenzophenone, 4,4 '-Dichlorobenzophenone, 2,2'-diethoxyacetophenone, 2,2'-dimethoxy-2-phenylacetophenone, dibenzosvelenone, 2,4-diethylthioxanthene-9-one, 4- (dimethylamino) benzophenone, Diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide, 1,4-dibenzoylbenzene, 4'-hydroxyacetophenone, 4-hydroxybenzophenone, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methylpro Piophenone, 2-hydroxy-4'-(2-hydroxyethoxy) -2-methylpropiophenone, 3-hydroxybenzophenone, 2-isopropylthioxanthone, phenyl (2,4,6-trimethylbenzoyl) lithium phosphinate, 2 -Methylbenzophenone, 3-methylbenzophenone, 2-methyl-4'-(methylthio) -2-morpholinopropiophenone, 9,10-phenanthrenquinone, 2-phenyl-2- (p-toluenesulfonyloxy) acetphenone and phenyl Examples thereof include bis (2,4,6-trimethylbenzoyl) phosphine oxide.
本発明の樹脂組成物には、樹脂組成物の硬化物の耐熱性などを向上させるためにラジカル重合性の化合物を併用することが好ましい。
ラジカル重合性の化合物の具体例としては、トリアリルイソシアヌレート、トリアリルシアヌレート、ジビニルベンゼン、イソフタル酸ジビニル、Ｎ−フェニル−マレイミド、Ｎ−フェニル−メチルマレイミド、Ｎ−フェニル−クロロマレイミド、Ｎ−ｐ−クロロフェニル−マレイミド、Ｎ−ｐ−メトキシフェニル−マレイミド、Ｎ−ｐ−メチルフェニル−マレイミド、Ｎ−ｐ−ニトロフェニル−マレイミド、Ｎ−ｐ−フェノキシフェニル−マレイミド、Ｎ−ｐ−フェニルアミノフェニル−マレイミド、Ｎ−ｐ−フェノキシカルボニルフェニル−マレイミド、１−マレイミド−４−アセトキシスクシンイミド−ベンゼン、４−マレイミド−４’−アセトキシスクシンイミド−ジフェニルメタン、４−マレイミド−４’−アセトキシスクシンイミド−ジフェニルエーテル、４−マレイミド−４’−アセトアミド−ジフェニルエーテル、２−マレイミド−６−アセトアミド−ピリジン、４−マレイミド−４’−アセトアミド−ジフェニルメタンおよびＮ−ｐ−フェニルカルボニルフェニル−マレイミド、Ｎ−エチルマレイミド、Ｎ−２．６−キシリルマレイミド、Ｎ−シクロヘキシルマレイミド、Ｎ−２，３−キシリルマレイミド、キシリルマレイミド、２，６−キシレンマレイミド、ビフェニルアラルキル型マレイミド及び４，４’−ビスマレイミドジフェニルメタン等が挙げられ、マレイミド基を有するマレイミド化合物が好ましい。
これらラジカル重合性の化合物は１種のみを併用してもよく、２種以上を併用してもよい。
本発明の樹脂組成物におけるラジカル重合性の化合物の含有量は、本発明の樹脂組成物の全固形分中に通常８０質量％以下、好ましくは１０乃至７０質量％である。
It is preferable to use a radically polymerizable compound in combination with the resin composition of the present invention in order to improve the heat resistance of the cured product of the resin composition.
Specific examples of the radically polymerizable compound include triallyl isocyanurate, triallyl cyanurate, divinylbenzene, divinyl isophthalate, N-phenyl-maleimide, N-phenyl-methylmaleimide, N-phenyl-chloromaleimide, and N-. p-chlorophenyl-maleimide, Np-methoxyphenyl-maleimide, Np-methylphenyl-maleimide, Np-nitrophenyl-maleimide, Np-phenoxyphenyl-maleimide, N-p-phenylaminophenyl- Maleimide, Np-phenoxycarbonylphenyl-maleimide, 1-maleimide-4-acetoxysuccinimide-benzene, 4-maleimide-4'-acetoxysuccinimide-diphenylmethane, 4-maleimide-4'-acetoxysuccinimide-diphenylether, 4-maleimide -4'-acetamide-diphenyl ether, 2-maleimide-6-acetamide-pyridine, 4-maleimide-4'-acetamide-diphenylmethane and N-p-phenylcarbonylphenyl-maleimide, N-ethylmaleimide, N-2.6- Examples thereof include xylylmaleimide, N-cyclohexylmaleimide, N-2,3-xylylmaleimide, xylylmaleimide, 2,6-xylenemaleimide, biphenylaralkyl-type maleimide and 4,4'-bismaleimide diphenylmethane, which are maleimide groups. A maleimide compound having is preferable.
Only one kind of these radically polymerizable compounds may be used in combination, or two or more kinds thereof may be used in combination.
The content of the radically polymerizable compound in the resin composition of the present invention is usually 80% by mass or less, preferably 10 to 70% by mass, in the total solid content of the resin composition of the present invention.
本発明の樹脂組成物には、有機溶剤を併用してもよい。
有機溶剤の具体例としては、トルエン及びキシレン等の芳香族系溶剤、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルモノアセテート及びプロピレングリコールモノブチルエーテル等のエーテル系溶剤、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン及びシクロヘキサノン等のケトン系溶剤、γ−ブチロラクトン及びγ−バレロラクトン等のラクトン類、Ｎ−メチルピロリドン（ＮＭＰ）、Ｎ，Ｎ−ジメチルホルムアミド（ＤＭＦ）、Ｎ，Ｎ−ジメチルアセトアミド及びＮ，Ｎ−ジメチルイミダゾリジノン等のアミド系溶剤、テトラメチレンスルフォン等のスルフォン類、等が挙げられる。
本発明の樹脂組成物における有機溶剤の含有量は、本発明の樹脂組成物の全固形分１００質量部に対して通常９００質量部以下、好ましくは４０乃至４００質量部である。
An organic solvent may be used in combination with the resin composition of the present invention.
Specific examples of the organic solvent include aromatic solvents such as toluene and xylene, ether solvents such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether monoacetate and propylene glycol monobutyl ether. Ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone and cyclohexanone, lactones such as γ-butyrolactone and γ-valerolactone, N-methylpyrrolidone (NMP), N, N-dimethylformamide (DMF), N, Examples thereof include amide-based solvents such as N-dimethylacetamide and N, N-dimethylimidazolidinone, and sulfones such as tetramethylene sulfone.
The content of the organic solvent in the resin composition of the present invention is usually 900 parts by mass or less, preferably 40 to 400 parts by mass, based on 100 parts by mass of the total solid content of the resin composition of the present invention.
本発明の樹脂組成物には、樹脂組成物の保存安定性を向上させるために重合禁止剤を併用してもよい。重合禁止剤は一般に公知のものが使用でき、例えば、ハイドロキノン、メチルハイドロキノン、ｐ−ベンゾキノン、クロラニル並びにトリメチルキノン等のキノン類、芳香族ジオール類及びジ−ｔ−ブチルヒドロキシトルエン等が挙げられる。 A polymerization inhibitor may be used in combination with the resin composition of the present invention in order to improve the storage stability of the resin composition. Generally known polymerization inhibitors can be used, and examples thereof include quinones such as hydroquinone, methylhydroquinone, p-benzoquinone, chloranil and trimethylquinone, aromatic diols and di-t-butylhydroxytoluene.
本発明の樹脂組成物は、その用途に応じて所望の性能を付与させる目的で本来の性能を損なわない範囲の量の充填剤や添加剤を配合して用いることができる。充填剤は繊維状であっても粉末状であってもよく、シリカ、カーボンブラック、アルミナ、タルク、雲母、ガラスビーズ及びガラス中空球等を挙げることができる。 The resin composition of the present invention can be used by blending an amount of a filler or an additive within a range that does not impair the original performance for the purpose of imparting desired performance according to the application. The filler may be fibrous or powdery, and examples thereof include silica, carbon black, alumina, talc, mica, glass beads, and glass hollow spheres.
本発明の樹脂組成物には、難燃性化合物、添加剤などの併用も可能である。これらは一般に使用されているものであれば、特に限定されるものではない。難燃性の化合物としては、例えば４，４−ジブロモビフェニルなどの臭素化合物、リン酸エステル、リン酸メラミン及びリン含有エポキシ樹脂等のリン化合物、メラミン及びベンゾグアナミンなどの窒素化合物、オキサジン環含有化合物、シリコン系化合物等が挙げられる。添加剤としては、紫外線吸収剤、酸化防止剤、光重合開始剤、蛍光増白剤、光増感剤、染料、顔料、増粘剤、滑剤、消泡剤、分散剤、レベリング剤、光沢剤等、所望に応じて適宜組み合わせて使用することも可能である。 Flame-retardant compounds, additives and the like can be used in combination with the resin composition of the present invention. These are not particularly limited as long as they are generally used. Examples of the flame-retardant compound include bromine compounds such as 4,4-dibromobiphenyl, phosphorus compounds such as phosphoric acid ester, melamine phosphate and phosphorus-containing epoxy resin, nitrogen compounds such as melamine and benzoguanamine, and oxazine ring-containing compounds. Examples include silicon-based compounds. Additives include UV absorbers, antioxidants, photopolymerization initiators, optical brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, defoaming agents, dispersants, leveling agents, brighteners. Etc., it is also possible to use them in combination as desired.
本発明の樹脂組成物は、さまざまな基材上に塗布あるいは含浸して使用することができる。例えばＰＥＴフィルム上に塗布して溶剤を除去した後に基材を剥離して得られるフィルム状接着剤は多層プリント基板の層間絶縁層として、ポリイミドフィルム上に塗布することによりカバーレイとして、また銅箔上に塗布乾燥することにより樹脂付き銅箔として使用することができる。またガラスクロスやガラスペーパー、カーボンファイバー、各種不織布などに含浸させることにより、プリント配線基板やＣＦＲＰのプリプレグとして使用することができる。また光ラジカル開始剤を用いることにより、パターニング可能なレジストとして用いることもできる。 The resin composition of the present invention can be applied or impregnated on various substrates for use. For example, a film-like adhesive obtained by applying it on a PET film to remove the solvent and then peeling off the base material can be used as an interlayer insulating layer of a multilayer printed circuit board, as a coverlay by applying it on a polyimide film, or as a copper foil. It can be used as a copper foil with resin by applying and drying it on top. Further, by impregnating glass cloth, glass paper, carbon fiber, various non-woven fabrics, etc., it can be used as a prepreg for a printed wiring board or CFRP. It can also be used as a patternable resist by using a photoradical initiator.
本発明の熱ラジカル開始剤を含む樹脂組成物は、必要によりホットプレス機などを用いて加熱により、また光ラジカル開始剤を含む樹脂組成物は公知の光照射機を用いて光照射により硬化物とすることができる。加熱条件や光照射条件は、樹脂組成物に用いる各成分の特性等を考慮して選択すればよい。 The resin composition containing the thermal radical initiator of the present invention is cured by heating using a hot press machine or the like, if necessary, and the resin composition containing the photoradical initiator is cured by light irradiation using a known light irradiator. Can be. The heating conditions and the light irradiation conditions may be selected in consideration of the characteristics of each component used in the resin composition.
以下、本発明を実施例、比較例により更に詳細に説明する。なお、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples. The present invention is not limited to these examples.
実施例１（本発明の高分子化合物の合成）
温度計、冷却管及び撹拌器を取り付けたフラスコに、ジアリルビスフェノールＡ（ＢＰＡ−ＣＡ、小西化学工業株式会社製）１００部（０．３２５モル）、トルエン５００部及びメトキノン０．５部を加え撹拌溶解させた後、トリエチルアミン１００部を加え９０℃まで昇温し、トルエン３００部に溶解させたテレフタル酸ジクロリド５９．３２部（０．２９２モル）を１０分間かけて滴下し、更に９０℃で３時間反応させた。反応によって生じたトリエチルアミン塩酸塩を濾過によって除去し、濾液を減圧下で濃縮することにより残存するトリエチルアミンをトルエンとともに留去した後、トルエン量を調整することにより本発明の高分子化合物１の３５％トルエン溶液３９４部を得た。得られた高分子化合物１の重量平均分子量は９，５００、数平均分子量は４，６００であった。尚、ここでいう重量平均分子量及び数平均分子量は、ゲルパーミエイションクロマトグラフィー（ＧＰＣ）の測定結果に基づいて、ポリスチレン換算で算出した値である。
Example 1 (Synthesis of Polymer Compound of the Present Invention)
Add 100 parts (0.325 mol) of diallyl bisphenol A (BPA-CA, manufactured by Konishi Chemical Industry Co., Ltd.), 500 parts of toluene and 0.5 part of methquinone to a flask equipped with a thermometer, a cooling tube and a stirrer, and stir. After dissolution, 100 parts of triethylamine was added and the temperature was raised to 90 ° C., 59.32 parts (0.292 mol) of terephthalic acid dichloride dissolved in 300 parts of toluene was added dropwise over 10 minutes, and further 3 at 90 ° C. Reacted for time. The triethylamine hydrochloride produced by the reaction was removed by filtration, and the filtrate was concentrated under reduced pressure to distill off the remaining triethylamine together with toluene, and then the amount of toluene was adjusted to make 35% of the polymer compound 1 of the present invention. 394 parts of a toluene solution was obtained. The weight average molecular weight of the obtained polymer compound 1 was 9,500, and the number average molecular weight was 4,600. The weight average molecular weight and the number average molecular weight referred to here are values calculated in terms of polystyrene based on the measurement results of gel permeation chromatography (GPC).
実施例２（本発明の末端変性高分子化合物の合成）
温度計、冷却管及び撹拌器を取り付けたフラスコに、ジアリルビスフェノールＡ（ＢＰＡ−ＣＡ、小西化学工業株式会社製）１００部（０．３２５モル）、トルエン５００部及びメトキノン０．５部を加え撹拌溶解させた後、触媒としてトリエチルアミン１００部を加え９０℃まで昇温し、トルエン３００部に溶解させたテレフタル酸ジクロリド５９．３２部（０．２９２モル）を１０分間かけて滴下し、更に９０℃で３時間反応させた。次いでトルエン１００部に溶解したメタクリル酸クロリド６．８１部を系中に加え、更に９０℃で２時間反応させた。反応によって生じたトリエチルアミン塩酸塩を濾過によって除去し、濾液を減圧下で濃縮することにより残存するトリエチルアミンをトルエンとともに留去した後、トルエン量を調整することにより本発明の末端変性高分子化合物１の３５％トルエン溶液４０６部を得た。得られた末端変性高分子化合物１の重量平均分子量は１１９００、数平均分子量は５６００であった。尚、ここでいう重量平均分子量及び数平均分子量はゲルパーミエイションクロマトグラフィー（ＧＰＣ）の測定結果に基づいて、ポリスチレン換算で算出した値である。
Example 2 (Synthesis of end-modified polymer compound of the present invention)
Add 100 parts (0.325 mol) of diallyl bisphenol A (BPA-CA, manufactured by Konishi Chemical Industry Co., Ltd.), 500 parts of toluene and 0.5 part of methquinone to a flask equipped with a thermometer, a cooling tube and a stirrer, and stir. After dissolution, 100 parts of triethylamine was added as a catalyst, the temperature was raised to 90 ° C., 59.32 parts (0.292 mol) of terephthalic acid dichloride dissolved in 300 parts of toluene was added dropwise over 10 minutes, and the temperature was further 90 ° C. Was reacted for 3 hours. Next, 6.81 parts of methacrylic acid chloride dissolved in 100 parts of toluene was added to the system, and the mixture was further reacted at 90 ° C. for 2 hours. The triethylamine hydrochloride produced by the reaction is removed by filtration, the filtrate is concentrated under reduced pressure to distill off the remaining triethylamine together with toluene, and then the amount of toluene is adjusted to obtain the terminal-modified polymer compound 1 of the present invention. 406 parts of a 35% toluene solution was obtained. The weight average molecular weight of the obtained terminally modified polymer compound 1 was 11,900, and the number average molecular weight was 5,600. The weight average molecular weight and the number average molecular weight referred to here are values calculated in terms of polystyrene based on the measurement results of gel permeation chromatography (GPC).
比較例１（比較用の高分子化合物の合成）
温度計、冷却管及び撹拌器を取り付けたフラスコに、ジアリルビスフェノールＡ（ＢＰＡ−ＣＡ、小西化学工業株式会社製）８０部（モル）、ビスフェノールＡ２０部、トルエン５００部及びメトキノン０．５部を加え撹拌溶解させた後、触媒としてトリエチルアミン１００部を加え９０℃まで昇温し、トルエン３００部に溶解させたテレフタル酸ジクロリド６３．４８部（０．３１３モル）を１０分間かけて滴下し、更に９０℃で３時間反応させた。反応によって生じたトリエチルアミン塩酸塩を濾過によって除去し、濾液を減圧下で濃縮することにより残存するトリエチルアミンをトルエンとともに留去した後、トルエン量を調整することにより比較用の高分子化合物１の３５％トルエン溶液４０２部を得た。得られた比較用の高分子化合物のトルエン溶液は、高温時には液体であったが、常温まで冷却すると結晶が析出して均一な溶液状態を維持できなかったため、以下に記載する実施例３乃至６に準じた方法によるサンプルの作製及び硬化物性評価が出来なかった。
Comparative Example 1 (Synthesis of Polymer Compound for Comparison)
Add 80 parts (mol) of diallyl bisphenol A (BPA-CA, manufactured by Konishi Chemical Industry Co., Ltd.), 20 parts of bisphenol A, 500 parts of toluene and 0.5 part of methquinone to a flask equipped with a thermometer, a cooling tube and a stirrer. After stirring and dissolving, 100 parts of triethylamine was added as a catalyst, the temperature was raised to 90 ° C., 63.48 parts (0.313 mol) of terephthalic acid dichloride dissolved in 300 parts of toluene was added dropwise over 10 minutes, and further 90 parts were added. The reaction was carried out at ° C. for 3 hours. The triethylamine hydrochloride produced by the reaction was removed by filtration, the filtrate was concentrated under reduced pressure to distill off the remaining triethylamine together with toluene, and then the amount of toluene was adjusted to 35% of the comparative polymer compound 1. 402 parts of a toluene solution was obtained. The obtained toluene solution of the polymer compound for comparison was a liquid at a high temperature, but when cooled to room temperature, crystals were precipitated and a uniform solution state could not be maintained. Therefore, Examples 3 to 6 described below could not be maintained. It was not possible to prepare a sample and evaluate the cured physical properties by the method according to the above.
実施例３及び４（本発明の樹脂組成物の調製）
実施例１及び２で得られた高分子化合物１及び末端変性高分子化合物１の溶液各１０部に、ラジカル開始剤としてジクミルパーオキサイド０．０６部を加えて均一に混合することにより、本発明の樹脂組成物を得た。
Examples 3 and 4 (preparation of the resin composition of the present invention)
By adding 0.06 part of dicumyl peroxide as a radical initiator to each of 10 parts of each of the solutions of the polymer compound 1 and the terminal-modified polymer compound 1 obtained in Examples 1 and 2, and uniformly mixing them, the present invention The resin composition of the present invention was obtained.
実施例５及び６（本発明のフィルム状接着剤の調製）
実施例３及び４で得られた樹脂組成物を、アプリケーターを用いてポリイミドフィルム上に厚さ２００μｍでそれぞれ塗布し、９０℃で１０分間加熱して溶剤を乾燥させることにより、本発明のフィルム状接着剤を得た。
Examples 5 and 6 (preparation of the film-like adhesive of the present invention)
The resin compositions obtained in Examples 3 and 4 were each applied to a polyimide film having a thickness of 200 μm using an applicator, and heated at 90 ° C. for 10 minutes to dry the solvent to form the film of the present invention. Obtained adhesive.
（樹脂組成物の硬化物の物性評価１）
実施例５及び６で得られた各フィルム状接着剤を、真空オーブン中で１８０℃１時間の条件で加熱することにより、フィルム状接着剤の硬化物を得た。得られた硬化物の厚さは７５μｍであり、フィルムとしての十分なフレキシビリティーと強度を有していた。前記で得られたそれぞれのフィルム状接着剤の硬化物について、ガラス転移温度を動的粘弾性測定装置ＥＸＳＴＡＲ６０００（セイコーエプソン株式会社製）を用いて、また１ＧＨｚにおける誘電率と誘電正接とをネットワークアナライザー８７１９ＥＴ（アジレントテクノロジー製）を用いて空洞共振法によって測定した。またＶ−０規格に準じて難燃性を確認した。結果を表１に示した。
(Evaluation of physical properties of cured product of resin composition 1)
Each of the film-like adhesives obtained in Examples 5 and 6 was heated in a vacuum oven at 180 ° C. for 1 hour to obtain a cured product of the film-like adhesive. The thickness of the obtained cured product was 75 μm, and it had sufficient flexibility and strength as a film. For each of the cured products of the film-like adhesives obtained above, the glass transition temperature was measured using a dynamic viscoelasticity measuring device EXSTAR6000 (manufactured by Seiko Epson Co., Ltd.), and the dielectric constant at 1 GHz and the dielectric loss tangent were measured by a network analyzer. It was measured by the cavity resonance method using 8719ET (manufactured by Azilent Technology). In addition, flame retardancy was confirmed according to the V-0 standard. The results are shown in Table 1.
実施例７及び８
実施例１及び２で得られた高分子化合物１及び末端変性高分子化合物１の各トルエン溶液１００部にシクロペンタノンを３００部加え、窒素を吹き込みながら１１０℃に加温することにより、トルエンを除去し、固形分濃度３５％のシクロペンタノン溶液を得た。前記で得られたシクロペンタノン溶液各１００部に、マレイミド樹脂としてＭＩＲ−３０００（日本化薬株式会社製）を表２に示す割合で配合し、ラジカル開始剤としてジクミルパーオキサイド０．０６部を加えて均一に混合することにより、本発明の樹脂組成物を得た。
Examples 7 and 8
Toluene is added to 100 parts of each toluene solution of the polymer compound 1 and the terminal-modified polymer compound 1 obtained in Examples 1 and 2 by adding 300 parts of cyclopentanone and heating to 110 ° C. while blowing nitrogen. It was removed to obtain a cyclopentanone solution having a solid content concentration of 35%. MIR-3000 (manufactured by Nippon Kayaku Co., Ltd.) as a maleimide resin was added to each 100 parts of the cyclopentanone solution obtained above in the proportion shown in Table 2, and 0.06 part of dicumyl peroxide as a radical initiator was added. Was added and mixed uniformly to obtain the resin composition of the present invention.
実施例９及び１０（本発明のフィルム状接着剤の調製）
実施例７及び８で得られた樹脂組成物を、アプリケーターを用いて厚さ１２μｍの銅箔（ＣＦ−Ｔ９ＦＺ：福田金属箔粉株式会社製）のマット面上に厚さ５０μｍでそれぞれ塗布し、９０℃で１０分間加熱して溶剤を乾燥させることにより本発明のフィルム状接着剤を有する銅箔を得た。
Examples 9 and 10 (Preparation of the film-like adhesive of the present invention)
The resin compositions obtained in Examples 7 and 8 were applied to a mat surface of a copper foil (CF-T9FZ: manufactured by Fukuda Metal Foil Powder Co., Ltd.) having a thickness of 12 μm using an applicator to a thickness of 50 μm. A copper foil having the film-like adhesive of the present invention was obtained by heating at 90 ° C. for 10 minutes to dry the solvent.
（樹脂組成物の硬化物の物性評価２）
実施例９及び１０で得られたフィルム状接着剤を有する銅箔の接着剤面上に、実施例９及び１０で用いたのと同じ銅箔のマット面を重ねあわせて真空プレス中で３ＭＰａの圧力で１時間加熱硬化させた後、銅箔間の９０°引きはがし強さ（接着強度）をオートグラフＡＧＸ−５０（株式会社島津製作所製）を用いて測定した。結果を表２に示した。
(Evaluation of physical properties of cured product of resin composition 2)
The same matte surface of the copper foil used in Examples 9 and 10 was superposed on the adhesive surface of the copper foil having the film-like adhesive obtained in Examples 9 and 10, and the pressure was 3 MPa in a vacuum press. After heat-curing with pressure for 1 hour, the 90 ° peeling strength (adhesive strength) between the copper foils was measured using Autograph AGX-50 (manufactured by Shimadzu Corporation). The results are shown in Table 2.
以上のように、本発明のランダム共重合体化合物及び末端変性高分子化合物は、高いフレキシビリティーを有し、優れた耐熱性、誘電特性、難燃性、接着性を示した。 As described above, the random copolymer compound and the terminal-modified polymer compound of the present invention have high flexibility and exhibit excellent heat resistance, dielectric properties, flame retardancy, and adhesiveness.
本発明の高分子化合物及び末端変性高分子化合物は、優れたフィルム形成能を有しながら耐熱性及び接着性が高く、かつ難燃性、誘電特性に優れるため、多層プリント基板の層間絶縁層等の用途に好適に用いることができる。
The polymer compound and the terminal-modified polymer compound of the present invention have excellent film-forming ability, high heat resistance and adhesiveness, and excellent flame retardancy and dielectric properties. Therefore, the interlayer insulating layer of a multilayer printed circuit board, etc. Can be suitably used for the above applications.
Claims (8)
で表される高分子化合物。 The following formula (1)
A polymer compound represented by.
で表される末端変性高分子化合物。 A terminally modified polymer compound which is a dehydrochloric acid reaction product of a polymer compound represented by the formula (1) according to claim 1 and a monocarboxylic acid chloride compound, and has the following formula (2).
A terminally modified polymer compound represented by.
The resin composition according to any one of claims 3 to 6, or the cured product of the film-like adhesive according to claim 7.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113980561A (en) * | 2021-11-11 | 2022-01-28 | 合肥工业大学 | UV (ultraviolet) curing hard coating and preparation method thereof |
| KR20220088582A (en) * | 2020-12-18 | 2022-06-28 | 주식회사 삼양사 | Polyester oligomer and method for preparing the same, and polyester-polycarbonate block copolymer comprising the oligomer with improved scratch resistance and method for preparing the same |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11184103A (en) * | 1997-12-25 | 1999-07-09 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus |
| JP2009503223A (en) * | 2005-09-13 | 2009-01-29 | エルジー・ケム・リミテッド | Novel polyarylate and process for producing the same |
| JP2010540746A (en) * | 2007-10-02 | 2010-12-24 | エルジー・ケム・リミテッド | Cured composition and cured product produced using the same |
| JP6408772B2 (en) * | 2014-03-14 | 2018-10-17 | ユニチカ株式会社 | Varnish and production method thereof |
| JP2019123767A (en) * | 2018-01-12 | 2019-07-25 | Dic株式会社 | Polyester resin and cured product thereof |
-
2019
- 2019-05-08 JP JP2019088456A patent/JP7267833B2/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11184103A (en) * | 1997-12-25 | 1999-07-09 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus |
| JP2009503223A (en) * | 2005-09-13 | 2009-01-29 | エルジー・ケム・リミテッド | Novel polyarylate and process for producing the same |
| JP2010540746A (en) * | 2007-10-02 | 2010-12-24 | エルジー・ケム・リミテッド | Cured composition and cured product produced using the same |
| JP6408772B2 (en) * | 2014-03-14 | 2018-10-17 | ユニチカ株式会社 | Varnish and production method thereof |
| JP2019123767A (en) * | 2018-01-12 | 2019-07-25 | Dic株式会社 | Polyester resin and cured product thereof |
Non-Patent Citations (1)
| Title |
|---|
| MIKITAEV, A. K., ET AL.: "Synthesis and study of properties of a high molecular-weight polyarylate based on 4,4'-dihydroxy-3,3", KRATKIE SOOBSHCHENIYA, vol. 25, no. 5, JPN6022055363, 1983, pages 363 - 365, ISSN: 0005010604 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20220088582A (en) * | 2020-12-18 | 2022-06-28 | 주식회사 삼양사 | Polyester oligomer and method for preparing the same, and polyester-polycarbonate block copolymer comprising the oligomer with improved scratch resistance and method for preparing the same |
| KR102625503B1 (en) | 2020-12-18 | 2024-01-17 | 주식회사 삼양사 | Polyester oligomer and method for preparing the same, and polyester-polycarbonate block copolymer comprising the oligomer with improved scratch resistance and method for preparing the same |
| CN113980561A (en) * | 2021-11-11 | 2022-01-28 | 合肥工业大学 | UV (ultraviolet) curing hard coating and preparation method thereof |
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