CN116724061A - Resin composition containing curable polymer compound - Google Patents
Resin composition containing curable polymer compound Download PDFInfo
- Publication number
- CN116724061A CN116724061A CN202280009145.0A CN202280009145A CN116724061A CN 116724061 A CN116724061 A CN 116724061A CN 202280009145 A CN202280009145 A CN 202280009145A CN 116724061 A CN116724061 A CN 116724061A
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- China
- Prior art keywords
- resin composition
- compound
- polymer compound
- copolymer
- present
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 71
- 239000011342 resin composition Substances 0.000 title claims abstract description 64
- 229920000642 polymer Polymers 0.000 title claims abstract description 61
- -1 phenylmaleimide compound Chemical class 0.000 claims abstract description 40
- 239000003999 initiator Substances 0.000 claims abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 16
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 14
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000853 adhesive Substances 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical group C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 claims description 6
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 description 39
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 15
- 239000011889 copper foil Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 10
- 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 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 6
- 238000010538 cationic polymerization reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- PJMXUSNWBKGQEZ-UHFFFAOYSA-N (4-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(O)C=C1 PJMXUSNWBKGQEZ-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000003960 organic solvent Substances 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
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 239000011229 interlayer Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000013034 phenoxy resin Substances 0.000 description 3
- 229920006287 phenoxy resin Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VMDQUQBEIFMAIC-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(C)=C1N1C(=O)C=CC1=O VMDQUQBEIFMAIC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical group ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-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
- 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 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- SUWCDVVTHPJCPX-UHFFFAOYSA-N naphthalene;prop-1-ene Chemical compound CC=C.C1=CC=CC2=CC=CC=C21 SUWCDVVTHPJCPX-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 150000007964 xanthones Chemical class 0.000 description 2
- ZODNDDPVCIAZIQ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)COC(=O)C=C ZODNDDPVCIAZIQ-UHFFFAOYSA-N 0.000 description 1
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 1
- IUSXXDHQFMPZQX-UHFFFAOYSA-N (2-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=CC=C1OC(=O)C=C IUSXXDHQFMPZQX-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
- NTHRHRINERQNSR-UHFFFAOYSA-N (3-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC(O)=C1 NTHRHRINERQNSR-UHFFFAOYSA-N 0.000 description 1
- DRZPXZMMDBMTHL-UHFFFAOYSA-N (3-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=CC(OC(=O)C=C)=C1 DRZPXZMMDBMTHL-UHFFFAOYSA-N 0.000 description 1
- NIUHGYUFFPSEOW-UHFFFAOYSA-N (4-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC=C(OC(=O)C=C)C=C1 NIUHGYUFFPSEOW-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
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-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
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
- PRZFFHNZHXGTRC-UHFFFAOYSA-N 1-(3-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=CC2=O)=O)=C1 PRZFFHNZHXGTRC-UHFFFAOYSA-N 0.000 description 1
- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 description 1
- QLDJXEMIAHBMSS-UHFFFAOYSA-N 1-(4-tert-butylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1N1C(=O)C=CC1=O QLDJXEMIAHBMSS-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
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-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
- 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
- GOAHRBQLKIZLKG-UHFFFAOYSA-N 1-tert-butylperoxybutane Chemical compound CCCCOOC(C)(C)C GOAHRBQLKIZLKG-UHFFFAOYSA-N 0.000 description 1
- SZVMZLJAAGWNPG-UHFFFAOYSA-N 1-tert-butylperoxyoctane Chemical compound CCCCCCCCOOC(C)(C)C SZVMZLJAAGWNPG-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
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-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
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-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
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-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
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The present invention provides a resin composition which can be formed into a film shape, and which has high heat resistance and adhesion of a cured product and low dielectric constant and dielectric tangent. The resin composition of the present invention comprises a polymer compound represented by the following formula (1), a compound capable of undergoing radical polymerization with the polymer compound, and a radical initiator, wherein the polymer compound is capable of undergoing radical polymerizationThe compound is at least one selected from the group consisting of (A) a phenylmaleimide compound, (B) an vinylnaphthalene compound, (C) a modified polyphenylene ether resin having an unsaturated double bond at the terminal, and (D) an allyl isocyanate compound.(wherein R is 1 R is R 2 Each independently represents a hydrogen atom or a methyl group. m and n are averages of the number of heavy units and are each independently in the range of 1 to 2,000).
Description
Technical Field
The present invention relates to a composition containing a curable polymer compound having a specific structure, which can be easily formed into a film by casting a solution onto a substrate, can be thermally or photo-cured, and has excellent dielectric properties, adhesion, and heat resistance of the cured product.
Background
The phenoxy resin is a high molecular weight polymer compound which can be obtained by polymerizing a difunctional epoxy resin and a difunctional phenol compound. Since a general epoxy resin composition or radical polymerizable composition can be formed into a film by adding such a phenoxy resin, it has been used as an important component of a film-like adhesive in a wide range of fields, particularly in the electric/electronic fields, an interlayer insulating layer of a printed circuit board, a resin-coated copper foil, and the like.
The cured product of the resin composition containing the phenoxy resin has excellent adhesion and film forming ability, but has low heat resistance and high dielectric constant and dielectric tangent (generally, dielectric constant is 3.5 at a frequency of 1GHz and dielectric tangent is about 0.03), so that it is practically impossible to use the cured product for electronic devices in which the signal response speed has been increased in recent years. Although a polymer fluorine compound such as Polytetrafluoroethylene (PTFE) or a liquid crystal polymer (patent document 2) is generally known as a resin having excellent dielectric characteristics, compatibility between these resins and other resins is extremely low, and adhesion is also insufficient. Patent document 3 describes a curable polymer compound obtained by esterification of an aliphatic hydroxyl group in a random copolymer of 70 wt% or less of a monomer having 1 ethylenically unsaturated group and 30 wt% or more of a (meth) acrylic acid ester having 1 or more aliphatic hydroxyl groups, with a monomer having 1 or more ethylenically unsaturated groups and 1 carboxyl group, but the present inventors have repeatedly confirmed that the cured product of the curable polymer compound of this document has a dielectric tangent of about 0.005 at 10GHz after repeated experiments and thus cannot sufficiently satisfy the low dielectric properties required for the current use of high frequency circuit boards.
[ Prior Art literature ]
[ patent literature ]
[ patent document 1] Japanese patent laid-open No. 2005-001274
[ patent document 2] Japanese patent application laid-open No. 2014-060449
[ patent document 3] Japanese patent laid-open No. 10-017812.
Disclosure of Invention
[ problem to be solved by the invention ]
The present invention has been made in view of the above-described problems, and an object of the present invention is to provide a composition which can be a cured product having sufficient flexibility to be formed into a film, high adhesion to a low-roughness copper foil, low dielectric constant and dielectric tangent, and high glass transition temperature.
[ means for solving the problems ]
As a result of intensive studies, the present inventors have found that a composition comprising a polymer compound having a specific structure, a compound having a specific structure capable of radical polymerization with the polymer compound, and a radical polymerization initiator can solve the above-mentioned problems, and have completed the present invention.
That is, the present invention relates to the following resin composition, film-like adhesive and cured product.
(1) A resin composition comprising a polymer compound represented by the following formula (1), a compound capable of undergoing radical polymerization with the polymer compound, and a radical initiator, wherein the compound capable of undergoing radical polymerization with the polymer compound is at least one selected from the group consisting of (A) a phenylmaleimide compound, (B) an vinylnaphthalene (sometimes referred to as acenaphthene) compound, (C) a modified polyphenylene ether resin having an unsaturated double bond at the terminal, and (D) an allyl isocyanate compound;
(wherein R is 1 R is R 2 Each independently represents a hydrogen atom or a methyl group. m and n are averages of the number of heavy units and are each independently in the range of 1 to 2,000);
(2) The resin composition according to the above (1), wherein the compound capable of undergoing radical polymerization with the polymer compound is a phenylmaleimide compound having one maleimide group in one molecule or a compound having one vinylnaphthalene structure in one molecule;
(3) A film-like adhesive comprising the resin composition of the preceding item (1) or (2); and
(4) A cured product of the resin composition according to the item (1) or (2) above or the film-like adhesive according to the item (3) above.
[ Effect of the invention ]
The resin composition of the present invention can be produced into a cured product by applying heat energy or light energy, and can provide a cured product excellent in dielectric characteristics, adhesion and heat resistance.
Detailed Description
Hereinafter, embodiments of the present invention will be described.
The polymer compound represented by the formula (1) which is an essential component of the resin composition of the present invention is a desalted acid condensate of a hydroxyl group "and a (meth) acrylic chloride group" which are contained in a random copolymer of a hydroxy phenyl (meth) acrylate and styrene, or a dehydrated condensate of a hydroxyl group "and a (meth) acrylic acid" which are contained in the copolymer.
First, a random copolymer of hydroxyphenyl (meth) acrylate and styrene (hereinafter, also simply referred to as "copolymer") which is an intermediate raw material for a polymer compound represented by formula (1) will be described.
Specific examples of the hydroxyphenyl (meth) acrylate which is a raw material of the copolymer include 4-hydroxyphenyl methacrylate, 2-hydroxyphenyl methacrylate, 3-hydroxyphenyl methacrylate, 4-hydroxyphenyl acrylate, 2-hydroxyphenyl acrylate, 3-hydroxyphenyl acrylate and the like, and 4-hydroxyphenyl methacrylate is preferable.
In addition, the "(meth) acrylate" as used herein means both "acrylate and methacrylate".
The following formula (2) is a structural formula of a random copolymer of hydroxy phenyl (meth) acrylate and styrene, R in the formula (2) 1 M and n represent R in formula (1) 1 M and n are synonymous. That is, the chemical polymer compound represented by the formula (1) (polymer compound having a structure represented by the formula (1)) is a polymer compound having a copolymer represented by the following formula (2) as an intermediate material.
The method of copolymerizing a hydroxyphenyl (meth) acrylate and styrene is not particularly limited as long as it is a well-known method, and examples thereof include: bulk polymerization, solution polymerization, emulsion polymerization, suspension polymerization, and the like.
Examples of the solvent that can be used in the solution polymerization include toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, propylene glycol monomethyl ether acetate, N-methylpyrrolidone (Methyl pyrrolidone), N-dimethylformamide, and γ -butyrolactone. In emulsion polymerization and suspension polymerization, water and a surfactant are generally used, and the raw material components are copolymerized in a state of being emulsified or suspended in water.
The copolymerization reaction may be any of radical polymerization, cationic polymerization, and anionic polymerization. In the radical polymerization, a radical polymerization initiator is preferably used. Specific examples of the radical polymerization initiator include 2,2' -azobisisobutyronitrile, 2' -azobis (2-methylbutyronitrile), 2' -azobis (2, 4-dimethylvaleronitrile), 1' -azobis (cyclohexane-1-carbonitrile, 2' -azobis [2- (2-imidazolin-2-yl) propane ] dihydrochloride, hydrogen peroxide, di-t-butyl peroxide, dicumyl peroxide, benzoyl peroxide, and the like.
The blending amount of the radical polymerization initiator is usually 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of the raw material components of the copolymer. The polymerization temperature is generally from 50 to 250℃and preferably from 60 to 200 ℃; the polymerization time is usually 0.5 to 30 hours, preferably 1 to 20 hours. In order to prevent the polymerization from being hindered by oxygen in the air, it is preferable that the radical polymerization reaction is carried out under a nitrogen atmosphere.
In the cationic polymerization, a cationic polymerization initiator may be used. Specific examples of the cationic polymerization initiator include inorganic acids such as sulfuric acid and hydrochloric acid, and CF 3 COOH and CCl 3 COOH and other organic acids, CF 3 SO 3 H and HClO 4 And (3) waiting for super acid.
In addition, in the case of anionic polymerization, an anionic polymerization initiator may be used. Specific examples of the anionic polymerization initiator include butyllithium, na-naphthalene complex, alkali metal, alkyl lithium compound, sodium amide (sodium amide), grignard reagent (Grignard reagent), and lithium alkoxide.
The amount of the cationic polymerization initiator or the anionic polymerization initiator to be blended is usually 0.01 to 5 parts by mass based on 100 parts by mass of the raw material components of the copolymer. The polymerization temperature is generally from 40 to 150℃and preferably from 50 to 120℃and the polymerization time is generally from 0.5 to 20 hours and preferably from 1 to 15 hours.
However, the ionic initiator used in the cationic polymerization or the anionic polymerization may remain in the copolymer after the polymerization reaction to adversely affect the dielectric characteristics or the insulation properties, and thus it is preferable to synthesize the copolymer as an intermediate raw material for the polymer compound represented by the formula (1) for radical polymerization.
The number average molecular weight of the copolymer to be an intermediate material for the polymer compound represented by the formula (1) is usually 3,000 to 300,000, preferably 5,000 to 200,000.
When the number average molecular weight is to be a copolymer within the above range, it is preferable to adjust the amount of the initiator used in synthesizing the copolymer to an appropriate amount. The amount of the initiator required for obtaining a copolymer having a number average molecular weight within the above range is not always limited to the type of the (meth) acrylate having a phenolic hydroxyl group and the amount of the (meth) acrylate having a hydroxyl group and styrene used in the copolymerization reaction, but it is generally known that a copolymer having a large molecular weight can be obtained by reducing the amount of the initiator, and the amount of the initiator to be blended may be selected so that a copolymer having a desired molecular weight can be obtained within the above range of the amount to be blended.
When the copolymer to be an intermediate raw material of the polymer compound represented by the formula (1) is synthesized, the ratio of the use of the hydroxyphenyl (meth) acrylate and the styrene is not particularly limited, but the amount (mass) of the styrene to be used is usually 4 to 99.7 times, preferably 4.5 to 99.5 times, the mass of the hydroxyphenyl (meth) acrylate. When the ratio of the raw materials of the copolymer is within the above range, the cured product of the resin composition of the present invention exhibits excellent dielectric characteristics (low dielectric constant and low dielectric tangent).
The polymer compound represented by the formula (1) can be obtained by a dehydrochlorination reaction of a phenolic hydroxyl group of the copolymer (a hydroxyl group of a hydroxyphenyl (meth) acrylate which is a raw material) and a chloride group of a (meth) acrylic chloride, or a dehydration condensation reaction of a phenolic hydroxyl group of the copolymer and a (meth) acrylic acid.
The ratio of the copolymer and the (meth) acrylic acid chloride or the (meth) acrylic acid used in synthesizing the polymer compound represented by the formula (1) is not particularly limited, but, for example, when the (meth) acrylic acid chloride or the (meth) acrylic acid is excessive or insufficient relative to the hydroxyl groups of the copolymer, the unreacted (meth) acrylic acid chloride or the (meth) acrylic acid or the hydroxyl groups remaining after the reaction with the (meth) acrylic acid chloride or the (meth) acrylic acid may have a bad influence on the properties of the cured product, and therefore, the (meth) acrylic acid chloride or the (meth) acrylic acid having the hydroxyl group equivalent to the hydroxyl groups of the copolymer is preferably used.
The reaction of the copolymer and the (meth) acrylic acid chloride may be carried out by adding the (meth) acrylic acid chloride to an organic solvent solution of the copolymer with stirring and allowing the mixture to react. The organic solvent that can be used at this time is not particularly limited as long as it can dissolve the copolymer and the (meth) acrylic acid chloride. When a copolymer which is to be an intermediate raw material is synthesized in a solvent, a copolymer solution after the polymerization reaction may be used as it is. The concentration of the copolymer solution used for the reaction with the (meth) acrylic acid chloride is usually 10 to 90 mass%, preferably 20 to 80 mass%. Further, the reaction temperature is usually 30 to 120 ℃, preferably 40 to 110 ℃, and the reaction time is usually 0.5 to 4 hours, preferably 1 to 3 hours.
Since the reaction between the copolymer and the (meth) acrylic acid chloride is a desalted acid reaction, it is preferable to add a tertiary amine such as triethylamine or pyridine to the reaction solution in advance in order to trap hydrochloric acid which is generated and further promote the reaction. The tertiary amine is used in an amount of preferably from equimolar to 4-fold mol based on the molar amount of the (meth) acrylic acid chloride, more preferably from equimolar to 3-fold mol. Since hydrochloric acid generated during the reaction is precipitated in the form of hydrochloride of amine, it can be removed by filtration after the reaction. In addition, the excess tertiary amine may be distilled off to the outside of the system after filtration under reduced pressure with heating.
The reaction of the copolymer and (meth) acrylic acid may be, for example, an esterification reaction well known in the art, and the method of carrying out the reaction may be, for example: a method of heating and stirring the copolymer and (meth) acrylic acid in the presence of a catalyst. Since the reaction between the copolymer and (meth) acrylic acid is a dehydration reaction, it is preferable to simultaneously azeotropically distill off water from the reaction system, and it is preferable to carry out the reaction using a solvent such as toluene, xylene, ethyl acetate, butyl acetate, methyl isobutyl ketone, etc., which is not completely mixed with water. The amount of the solvent to be used is preferably an amount such that the concentration of the raw material component of the polymer compound represented by the formula (1) becomes 20 to 80 mass%.
Examples of the catalyst used in the esterification reaction include: the amount of the acidic catalyst such as sulfuric acid, methanesulfonic acid, and p-toluenesulfonic acid to be used is preferably 0.1 to 5% by mass based on the total mass of the raw material components of the polymer compound represented by the formula (1) and the solvent used in the reaction. The reaction temperature is usually 50 to 150℃and preferably 60 to 140℃and the reaction time is usually 0.5 to 4 hours and preferably 1 to 3 hours.
In order to prevent polymerization reaction between (meth) acryloyl groups in the polymer compound represented by formula (1) and to improve the storage stability of the polymer compound represented by formula (1), it is preferable to add a small amount of a polymerization inhibitor to the polymer compound solution after completion of the synthesis reaction. Specific examples of the polymerization inhibitor include hydroquinone, p-methoxyphenol, methylhydroquinone, di-t-butylhydroxytoluene, t-butylhydroquinone, 2-t-butyl-1, 4-benzoquinone, 1-diphenyl-2-trinitrophenylhydrazine (1, 1-diphenyl-2-picrylhydrazyl) radical, 6-t-butyl-2, 4-xylenol, 4-t-butylcatechol, 2, 6-di-t-butylphenol, 2, 6-di-t-butyl-p-cresol, phenothiazine, and the like.
The range of the number average molecular weight of the polymer compound represented by the formula (1) obtained in this way is preferably 11,000 to 300,000, more preferably 15,000 to 200,000. When the molecular weight is less than the above range, the adhesion to the low-roughness copper foil becomes low, and when the molecular weight is more than the above range, the viscosity becomes high, and coating becomes difficult in some cases.
The molecular weight in the present specification means a value calculated by converting polystyrene based on the measurement result of GPC.
The resin composition of the present invention contains at least one compound selected from the group consisting of (A) a phenylmaleimide compound, (B) an vinylnaphthalene compound, (C) a modified polyphenylene ether resin having an unsaturated double bond at the terminal, and (D) an allyl isocyanate compound, as a compound capable of radical polymerization with a polymer compound represented by formula (1).
(A) Phenylmaleimide compound (hereinafter, abbreviated as "(A) component")
The component (a) which can be contained in the resin composition of the present invention is added for the purpose of copolymerizing it with an unsaturated double bond group at the terminal of a side chain of the polymer compound represented by the formula (1), and the number of maleimide groups in the compound is not particularly limited, but a phenylmaleimide compound having one maleimide group in one molecule is preferable.
(A) Examples of the components include: n-phenylmaleimide, N- (2-methylphenyl) maleimide, N- (3-methylphenyl) maleimide, N- (4-methylphenyl) maleimide, N- (2, 6-dimethylphenyl) maleimide, N- (4-tert-butylphenyl) maleimide and the like, N-phenylmaleimide being preferred.
The content of the component (a) in the resin composition of the present invention is usually 3 to 50 parts by mass, preferably 5 to 40 parts by mass, relative to 100 parts by mass of the polymer compound represented by the formula (1). When the content ratio of the polymer compound represented by the formula (1) and the component (A) is in the above-mentioned range, excellent properties of the cured product of the resin composition of the present invention are exhibited.
(B) Vinyl naphthalene compound (hereinafter, simply referred to as "(component B"))
The component (B) that can be contained in the resin composition of the present invention is added for the purpose of copolymerizing it with an unsaturated double bond group at the terminal of a side chain of the polymer compound represented by formula (1), and the number of vinylnaphthalene structures in the compound is not particularly limited, but a vinylnaphthalene compound having 1 vinylnaphthalene structure in 1 molecule is preferable.
(B) Examples of the components include: ethylene naphthalene, 3-methyl ethylene naphthalene, 4-methyl ethylene naphthalene, 5-methyl ethylene naphthalene, 3, 8-two methyl ethylene naphthalene, 3, 7-two methyl ethylene naphthalene, etc., preferably ethylene naphthalene.
The content of the component (B) in the resin composition of the present invention is usually 3 to 50 parts by mass, preferably 5 to 40 parts by mass, relative to 100 parts by mass of the polymer compound represented by the formula (1). When the content ratio of the polymer compound represented by the formula (1) and the component (B) is in the above-mentioned range, excellent properties of the cured product of the resin composition of the present invention are exhibited.
(C) Modified polyphenylene ether resin having an unsaturated double bond at the terminal (hereinafter, simply referred to as "(component C"))
The component (C) which can be contained in the resin composition of the present invention is preferably a modified polyphenylene ether resin having a methacryloyl group, an acryl group or a vinyl group at both ends of the molecule and a number average molecular weight of 1,000 to 10,000. Specific examples thereof include: a compound represented by the following formula (3) having a methacryloyl group at both ends and a number average molecular weight of about 1,700 (trade name SA9000, manufactured by japan SABIC liability co., ltd.), a compound represented by the following formula (4) having a vinyl group at both ends and a number average molecular weight of about 1,200 or 2,200 (trade name OPE-2st 1200 or OPE-2st 2200, manufactured by mitsubishi gas chemistry co., ltd.), or the like.
The content of the component (C) in the resin composition of the present invention is usually 3 to 50 parts by mass, preferably 5 to 40 parts by mass, relative to 100 parts by mass of the polymer compound represented by the formula (1).
(D) Allyl isocyanate compound (hereinafter, abbreviated as "(D) component")
The component (D) that can be contained in the resin composition of the present invention is preferably an allyl isocyanate compound having an isocyanate structure and two or more allyl groups in one molecule, and examples thereof include: triallyl isocyanurate, 1, 3-diallyl-5-methoxycarbonyl-1, 3, 5-triazine-2, 4,6 (1 h,3h,5 h) -trione, 1, 3-diallyl-5- (cyclohexen-4-yl) methoxycarbonyl-1, 3, 5-triazine-2, 4,6 (1 h,3h,5 h) -trione, and the like. In addition, as an example of the allyl isocyanate compound having two allyl groups, L-DAIC manufactured by four chemical industries, inc. may be mentioned.
The monoallyl isocyanate compound having a functional group other than an allyl group which is reactive with the polymer compound represented by the formula (1) is also included in the category of the component (D) contained in the composition of the present invention.
The content of the component (D) in the resin composition of the present invention is usually 3 to 50 parts by mass, preferably 5 to 40 parts by mass, relative to 100 parts by mass of the polymer compound represented by the formula (1). The content of the component (D) in the polymer compound represented by the formula (1) is in the above range, whereby excellent properties of the cured product of the resin composition of the present invention are exhibited.
The resin composition of the present invention contains a radical initiator. The radical initiator may be any of a thermal radical initiator and a photo radical initiator.
More preferred thermal radical initiators include, for example: peroxides such as benzoyl peroxide, cumene hydroperoxide, 2, 5-dihydro-2, 5-dimethylhexane, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexyne-3, di-t-butyl peroxide, t-butylisopropyl peroxide, α -bis (t-butylperoxy-m-isopropyl) benzene, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, dicumyl peroxide, di-t-butyl peroxyisophthalate, t-butyl peroxybenzoate, 2-bis (t-butylperoxy) butane, 2-bis (t-butylperoxy) octane, 2, 5-dimethyl-2, 5-di (benzoyl peroxy) hexane, bis (trimethylsilyl) peroxide, and trimethylsilyl triphenylsilyl peroxide.
Examples of more preferred photo radical initiators include: benzoin and its alkyl ethers such as benzoin methyl ether, benzoin ethyl ether, etc.; acetophenones such as acetophenone, 2-dimethoxy-2-phenylacetophenone, and 1, 1-dichloroacetophenone; anthraquinones such as 2-methylanthraquinone, 2-pentylalnthraquinone, 2-t-butylanthraquinone, and 1-chloroanthraquinone; thioxanthones (thioxanthones) such as 2, 4-dimethylthioxanthone, 2, 4-diisopropylthioxanthone and 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone such as benzophenone; 2-methyl-1- [4- (methylsulfanyl) phenyl ] -2-morpholino-propan-1-one or 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butanone-1; acyl phosphine oxides, xanthones (xanthones), and the like.
The content of the radical initiator in the resin composition of the present invention is usually 0.1 to 10 parts by mass, preferably 0.1 to 8 parts by mass, based on 100 parts by mass of the total of the resin components such as the polymer compound represented by the formula (1), the compound capable of undergoing radical polymerization with the polymer compound represented by the formula (1), and the radical-reactive monomer of any component described later.
The resin composition of the present invention may contain a radical-reactive monomer. The use of a radical-reactive monomer in combination can improve the reactivity of the resin composition of the present invention, the heat resistance of the cured product, and the like. The radical reactive monomer preferably has 2 or more functional groups, and specific examples thereof include: ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, 1, 4-butanediol dimethacrylate, neopentyl glycol dimethacrylate, 1, 6-hexanediol dimethacrylate, 1, 9-nonanedioldimethacrylate, glycerol dimethacrylate, 2-hydroxy-3-acryloxypropyl methacrylate, ethylene oxide adduct methacrylate of bisphenol A, trimethylolpropane trimethacrylate, tricyclodecanedimethanol dimethacrylate, glycerol dimethacrylate, trimethylolpropane trimethacrylate, ethoxylated isocyanatotriacrylate, epsilon-caprolactone-modified ginseng- (2-acryloxyethyl) isocyanurate, pentaerythritol triacrylate, ditrimethyloltetraacrylate, ethoxylated pentaerythritol tetraacrylate, dipentaerythritol polyacrylate, dipentaerythritol hexaacrylate, triallyl isocyanurate, divinylbenzene, diethylene phthalate, N-phenyl-maleimide, N-phenyl-methyl maleimide, N-phenyl-dicarboximide, N-butenyl-p-chlorophenyl-maleimide, N-butenyl-p-phenylene-maleimide, N-phenylene-N-2-butenyl-dicarboximide, N-p-phenylene-4-phenylene-maleimide, N-phenylene-N-4-phenylmaleimide, N-p-phenylene-dicarboximide, N-phenylene-4-dicarboximide, p-phenylene-N-phenylmaleimide, N-p-phenylene-4-phenylmaleimide, 4-maleimide-4 ' -acetoxysuccinimide-diphenylmethane, 4-maleimide-4 ' -acetoxysuccinimide-diphenylether, 4-maleimide-4 ' -acetamide-diphenylether, 2-maleimide-6-acetamide-pyridine, 4-maleimide-4 ' -acetamide-diphenylmethane and N-p-phenylcarbonylphenyl-maleimide N-ethylcarbodiimide, N-2.6-xylylmaleimide, N-cyclohexylmaleimide, N-2, 3-xylylmaleimide, 2, 6-xylylmaleimide and 4,4' -bismaleimide diphenylmethane and the like, but those having a maleimide group as a functional group (maleimide compound) are preferable.
These radical-reactive monomers may be used alone or in combination of two or more.
In the resin composition of the present invention, an organic solvent may be used in combination. 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 monomethyl ether monoacetate, and propylene glycol monobutyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone; lactones such as gamma-butyrolactone and gamma-valerolactone; amide solvents such as N-methylpyrrolidone (Methyl pyrrolidone) (NMP), N-Dimethylformamide (DMF), N-dimethylacetamide and N, N-dimethylimidazolidinone; sulfones such as tetramethylene sulfone, and the like. The content of the organic solvent in the resin composition of the present invention is usually 90 mass% or less, preferably 30 to 80 mass% in the resin composition.
The resin composition of the present invention may be used in combination with a polymerization inhibitor to improve storage stability. The polymerization inhibitor to be used in combination is not particularly limited as long as it is a generally known polymerization inhibitor, and examples thereof include: quinone such as hydroquinone, methyl hydroquinone, p-benzoquinone, tetrachlorobenzoquinone and trimethylquinone, aromatic glycols, di-t-butylhydroxytoluene, etc.
The resin composition of the present invention can be formulated and used in an amount within a range that does not impair the original properties, depending on the purpose of imparting desired properties to the resin composition. The filler may be fibrous or powdery, and examples thereof include silica, carbon black, alumina, talc, mica, glass beads, and glass hollow spheres.
The resin composition of the present invention may be used in combination with a flame retardant compound, an additive, or the like. 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, phosphate esters, melamine phosphate, phosphorus-containing epoxy resins, nitrogen compounds such as melamine or benzoguanamine (benzoguanamine), oxazine ring-containing compounds, silicon compounds, and the like. The additives can be listed as follows: ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, tackifiers, slip agents, defoamers, dispersants, leveling agents (leveling agents), and gloss agents may be used in combination as appropriate as desired.
The resin composition of the present invention can be used by coating or impregnating various substrates. For example, when a thermal radical initiator is used, it can be used as an interlayer insulating layer of a multilayer printed circuit board by coating on a PET film, as a cover layer (coverlay) by coating on a polyimide film, or as a resin-coated copper foil by coating and drying on a copper foil. Further, the prepreg may be impregnated with glass cloth, glass paper, carbon fiber, various nonwoven fabrics, or the like, and thus may be used as a prepreg for a printed circuit board or CFRP. In addition, it is also possible to use the photo radical initiator as various resists.
The interlayer insulating layer or the cover layer, the resin-coated copper foil, the prepreg, and the like containing the resin composition of the present invention can be molded by heating and pressing with a hot press or the like to prepare a cured product.
Examples (example)
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. In addition, the present invention is not limited to these examples.
Synthesis example 1 (Synthesis of Polymer Compound contained in formula (1))
(step 1) Synthesis of copolymer (copolymer 1) represented by the following formula (5)
Into a flask equipped with a thermometer, a cooling tube, a nitrogen inlet tube, and a stirrer, 38.5 parts of styrene, 1.5 parts of 4-hydroxyphenyl methacrylate, 0.4 parts of benzoyl peroxide, and 10 parts of Propylene Glycol Monomethyl Ether Acetate (PGMEA) were charged, and reacted under a nitrogen atmosphere at 120 to 130 ℃ for 5 hours, whereby a PGMEA solution of copolymer 1 represented by the following formula (5) was obtained. A part of the above PGMEA solution was heated under reduced pressure, and the amount of copolymer 1 was calculated as 34.2 parts by taking the dry mass obtained by removing the solvent and unreacted styrene as the solid content, and if 5.8 parts of unreacted styrene were considered, the copolymer was obtained as a copolymer of 32.7 parts of styrene and 1.5 parts of 4-hydroxyphenyl methacrylate. The number average molecular weight of the sample used for the measurement of the dry mass was 38,000, and the weight average molecular weight was 161,000. From the copolymerization ratio and the number average molecular weight of styrene and 4-hydroxyphenyl methacrylate, n in formula (5) was calculated to be 361 and m was calculated to be 9.
(step 2) Synthesis of Polymer Compound (Polymer Compound 1) represented by the following formula (6)
From the PGMEA solution of the copolymer 1 obtained in step 1, after unreacted styrene and PGMEA were distilled off together under a reduced pressure by heating, PGMEA was further added to obtain 138 parts of a 25 mass% solution of the copolymer 1. To this solution, 5 parts of triethylamine was added, and after the temperature of the solution was set to 60℃with stirring, 0.88 parts of methacrylic acid chloride was added thereto in this state to react for 1 hour. The reaction solution was filtered under pressure using a filter paper having a sufficient particle diameter of 1 μm to remove triethylamine hydrochloride, excess triethylamine and PGMEA were distilled off from the filtrate by a rotary evaporator, and the amount of PGMEA was adjusted, whereby 139 parts of a solution containing 25 mass% of the polymer compound (polymer compound 1) of the present invention represented by the following formula (6) was obtained. The number average molecular weight of the obtained polymer compound 1 was 40,000, and the weight average molecular weight was 164,000.
Example 1 (preparation of the resin composition of the invention)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide and 1.1 part of N-phenylmaleimide were added as a radical initiator, and the mixture was uniformly mixed, thereby obtaining a resin composition 1 of the present invention.
Example 2 (preparation of the resin composition of the invention)
To 10 parts of PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide and 1.1 part of vinylnaphthalene were added as a radical initiator, and the mixture was uniformly mixed to obtain a resin composition 2 of the present invention.
Example 3 (preparation of the resin composition of the invention)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide and 0.3 part of a modified polyphenylene ether resin (SA-9000) were added as a radical initiator, and the mixture was uniformly mixed to obtain a resin composition 3 of the present invention.
Example 4 (preparation of the resin composition of the invention)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide and 0.6 part of a modified polyphenylene ether resin (SA-9000) were added as a radical initiator, and the mixture was uniformly mixed to obtain a resin composition 4 of the present invention.
Example 5 (preparation of the resin composition of the invention)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in Synthesis example 1, 0.05 part of dicumyl peroxide and 0.38 part of L-DAIC (manufactured by Kagaku Co., ltd.) were added as a radical initiator, and the mixture was uniformly mixed to obtain a resin composition 5 of the present invention.
Example 6 (preparation of the resin composition of the invention)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide and 0.38 part of triallyl isocyanurate (manufactured by mitsubishi chemical Co., ltd.) were added as a radical initiator, and the mixture was uniformly mixed, thereby obtaining a resin composition 6 of the present invention.
Comparative example 1 (preparation of comparative resin composition)
To 10 parts of the PGMEA solution of the polymer compound 1 obtained in synthesis example 1, 0.05 part of dicumyl peroxide was added as a radical initiator, and the mixture was uniformly mixed to obtain a comparative resin composition 7.
(evaluation of dielectric Properties, glass transition temperature and linear expansion Rate of cured article of resin composition)
The resin compositions 1 to 7 obtained in examples 1 to 6 and comparative example 1 were each coated on a mirror surface of a copper foil having a thickness of 18 μm with a thickness of 280 μm by using an applicator (applicator), and the solvent was dried by heating at 90℃for 10 minutes, thereby obtaining a copper foil having a film-like adhesive composed of the resin composition. The film-like adhesive on the copper foil obtained above was heated and cured at 180℃for 1 hour using a vacuum oven, and then immersed in an etching solution to remove the copper foil, whereby cured products of the film-like adhesive having a thickness of 70 μm were obtained, which were each capable of being handled as a film. The dielectric constant and dielectric tangent of the cured product obtained above at 10GHz were measured by a cavity resonance method using a network analyzer 8719ET (manufactured by Agilent Technologies Co.). The glass transition temperature and α1 (linear expansion coefficient in the glassy region) of the cured product obtained above were measured by TMA (thermo-mechanical property device). The results are presented in table 1.
(evaluation of adhesive Strength of cured article of resin composition)
The resin compositions 1 to 7 obtained in examples 1 to 6 and comparative example 1 were each coated on an unpolished side of a low-roughness copper foil (CF-T4X-SV; manufactured by Fufield Metal foil powder Co., ltd.) for high frequency having a thickness of 12. Mu.m, at a thickness of 50. Mu.m, with an applicator, and heated at 90℃for 10 minutes to dry the solvent, whereby a copper foil having a film-like adhesive composed of the resin composition of the present invention was obtained. The adhesive surface of the resin-coated copper foil was laminated with an unpolished surface of the same copper foil as described above, and the laminate was heat-cured under vacuum at a pressure of 3MPa for 1 hour, and then the 90 ° peel strength (adhesive strength) between the copper foils was measured using an audiogram AGX-50 (manufactured by shimadzu corporation). The results are presented in table 1.
TABLE 1
Table 1 evaluation results of cured products of resin compositions
As described above, the cured product of the resin composition of the present invention forms a flexible film and further exhibits excellent dielectric characteristics, heat resistance and adhesion.
Claims (4)
1. A resin composition comprising a polymer compound represented by the following formula (1), a compound capable of undergoing radical polymerization with the polymer compound, and a radical initiator, wherein the compound capable of undergoing radical polymerization with the polymer compound is at least one selected from the group consisting of (A) a phenylmaleimide compound, (B) an vinylnaphthalene compound, (C) a modified polyphenylene ether resin having an unsaturated double bond at the terminal, and (D) an allyl isocyanate compound;
wherein R is 1 R is R 2 Each independently represents a hydrogen atom or a methyl group; m and n are averages of the number of heavy units and are each independently in the range of 1 to 2,000.
2. The resin composition according to claim 1, wherein the compound capable of undergoing radical polymerization with the polymer compound is a phenylmaleimide compound having one maleimide group in one molecule or a compound having one vinylnaphthalene structure in one molecule.
3. A film-like adhesive comprising the resin composition according to claim 1 or 2.
4. A cured product of the resin composition according to claim 1 or 2 or the film-like adhesive according to claim 3.
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| JP2021-037073 | 2021-03-09 | ||
| JP2021-101268 | 2021-06-18 | ||
| JP2021-128159 | 2021-08-04 | ||
| JP2021128159 | 2021-08-04 | ||
| PCT/JP2022/009327 WO2022191056A1 (en) | 2021-03-09 | 2022-03-04 | Resin composition including curable polymer compound |
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| CN116724061A true CN116724061A (en) | 2023-09-08 |
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