CN113260646B - Aromatic amine resin, maleimide resin, curable resin composition, and cured product thereof - Google Patents
Aromatic amine resin, maleimide resin, curable resin composition, and cured product thereof Download PDFInfo
- Publication number
- CN113260646B CN113260646B CN202080007530.2A CN202080007530A CN113260646B CN 113260646 B CN113260646 B CN 113260646B CN 202080007530 A CN202080007530 A CN 202080007530A CN 113260646 B CN113260646 B CN 113260646B
- Authority
- CN
- China
- Prior art keywords
- resin
- aromatic amine
- acid
- maleimide
- bis
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims abstract description 151
- 239000011347 resin Substances 0.000 title claims abstract description 151
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 47
- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims abstract description 38
- -1 aniline compound Chemical group 0.000 claims description 101
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims description 7
- OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical compound O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 10
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 8
- 238000007789 sealing Methods 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 16
- 239000003822 epoxy resin Substances 0.000 description 15
- 229920000647 polyepoxide Polymers 0.000 description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
- 229910052698 phosphorus Inorganic materials 0.000 description 13
- 239000011574 phosphorus Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000004927 clay Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- 239000005011 phenolic resin Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
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- 239000000463 material Substances 0.000 description 10
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- 239000000243 solution Substances 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 8
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000004643 cyanate ester Substances 0.000 description 8
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 8
- 239000003566 sealing material Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000004848 polyfunctional curative Substances 0.000 description 7
- 239000011973 solid acid Substances 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920000049 Carbon (fiber) Polymers 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- TYMZLIDQEUWXEL-UHFFFAOYSA-N bis(2,3-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(OP(O)(=O)OC=2C(=C(C)C=CC=2)C)=C1C TYMZLIDQEUWXEL-UHFFFAOYSA-N 0.000 description 6
- 239000004917 carbon fiber Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000010533 azeotropic distillation Methods 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 229910000064 phosphane Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 4
- BVKSYBQAXBWINI-LQDRYOBXSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]propanoy Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCCN=C(N)N BVKSYBQAXBWINI-LQDRYOBXSA-N 0.000 description 3
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 3
- SSPMJQOASMQREI-UHFFFAOYSA-N 1-(methoxymethyl)-2-phenylbenzene Chemical group COCC1=CC=CC=C1C1=CC=CC=C1 SSPMJQOASMQREI-UHFFFAOYSA-N 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
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- 229920002050 silicone resin Polymers 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical class CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- XGSHEASGZHYHBU-UHFFFAOYSA-N tetradecane-1,1-diamine Chemical compound CCCCCCCCCCCCCC(N)N XGSHEASGZHYHBU-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- FRXCPDXZCDMUGX-UHFFFAOYSA-N tridecane-1,1-diamine Chemical compound CCCCCCCCCCCCC(N)N FRXCPDXZCDMUGX-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CAPOZRICGSDRLP-UHFFFAOYSA-N tris(2,3-dimethylphenyl) phosphate Chemical compound CC1=CC=CC(OP(=O)(OC=2C(=C(C)C=CC=2)C)OC=2C(=C(C)C=CC=2)C)=C1C CAPOZRICGSDRLP-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- JRHDFVNUWLMGBU-UHFFFAOYSA-L zinc octyl phosphate Chemical compound C(CCCCCCC)OP(=O)([O-])[O-].[Zn+2] JRHDFVNUWLMGBU-UHFFFAOYSA-L 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- IJQXGKBNDNQWAT-UHFFFAOYSA-L zinc;docosanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O IJQXGKBNDNQWAT-UHFFFAOYSA-L 0.000 description 1
- PORPEXMDRRVVNF-UHFFFAOYSA-L zinc;octadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O PORPEXMDRRVVNF-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
Abstract
The purpose of the present invention is to provide an aromatic amine resin having a specific structure and excellent in solvent solubility. Further, an object of the present invention is to provide a curable resin composition and a cured product thereof, which are preferably used for sealing of electric and electronic parts, circuit boards, carbon fiber composites, and the like, have high heat resistance and excellent low dielectric characteristics, and contain a maleimide resin derived from an aromatic amine having a specific structure. An aromatic amine resin represented by the following formula (1). In the formula (1), R 1 、R 2 、R 3 Represents a hydrocarbon group having 1 to 18 carbon atoms. m represents an integer of 1 to 4, n represents an average value, and 1+.n+.20.
Description
Technical Field
The present invention relates to an aromatic amine resin, a maleimide resin derived therefrom, a curable resin composition using the same, and a cured product thereof, and is preferably used for an electrical and electronic component such as a semiconductor sealing material, a printed wiring board, a laminate, or a lightweight high-strength material such as a carbon fiber reinforced plastic or a glass fiber reinforced plastic.
Background
In recent years, a laminate board on which an electric and electronic component is mounted is demanded to have wide characteristics and a high degree of height due to expansion of its application field. A conventional semiconductor chip is mainly mounted on a metal lead frame, but a semiconductor chip having high processing capacity such as a central processing unit (hereinafter, referred to as a CPU (central processing unit (central processing unit))) is often mounted on a laminate made of a polymer material.
In particular, in a semiconductor package (hereinafter, referred to as PKG) used for a smart phone or the like, the PKG substrate is required to be thinned in order to meet the demands for miniaturization, thinning, and densification, but if the PKG substrate is thinned, rigidity is lowered, and thus, a large warpage or the like is caused by heating at the time of soldering the PKG to a motherboard (printed circuit board (printed circuit board, PCB)). In order to reduce this aspect, a PKG substrate material with a high Tg above the solder mounting temperature is required.
In addition, the fifth generation communication system "5G" currently under accelerated development is expected to further advance the capacity and high-speed communication. The need for low dielectric loss tangent materials is increasing, and dielectric loss tangents of at least 0.005 or less at 1GHz are required.
Further, in the field of automobiles, there is a case where precision electronic equipment is disposed in the vicinity of an engine driving part, and thus, a higher level of heat and humidity resistance is required. SiC semiconductors have been used for electric vehicles, air conditioners, and the like, and extremely high heat resistance has been required for sealing materials for semiconductor elements, so that conventional epoxy resin sealing materials have failed to cope with.
Under such circumstances, polymer materials having both heat resistance and low dielectric loss tangent characteristics have been studied. For example, patent document 1 proposes a composition containing a maleimide resin and a phenol resin containing a propylene group. However, on the other hand, the phenolic hydroxyl group which does not participate in the reaction remains at the time of the hardening reaction, and thus the electrical characteristics cannot be said to be sufficient. Patent document 2 discloses an allyl ether resin in which an allyl group is substituted for a hydroxyl group. However, the claisen rearrangement (Claisen Rearrangement) is caused at 190 ℃, and a phenolic hydroxyl group which does not contribute to the hardening reaction is formed at 200 ℃ which is a molding temperature of a general substrate, and thus electrical characteristics cannot be satisfied.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 04-359911
Patent document 2: international publication No. 2016/002704
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of such circumstances, and an object thereof is to provide an aromatic amine resin, a curable resin composition, and a cured product thereof, which exhibit excellent heat resistance and electrical characteristics and have good curability.
Technical means for solving the problems
The present inventors have conducted intensive studies to solve the above problems, and as a result, have found a novel aromatic amine resin. Further, it has been found that a cured product of a curable resin composition containing a maleimide resin derived from an aromatic amine resin is excellent in heat resistance and low dielectric characteristics, and the present invention has been completed.
That is, the present invention relates to the following [1] to [9].
[1]
An aromatic amine resin represented by the following formula (1).
[ chemical 1]
(in the formula (1), R 1 、R 2 、R 3 Represents a hydrocarbon group having 1 to 18 carbon atoms. m represents an integer of 1 to 4, n represents an average value, and 1+.n+.20).
[2]
The aromatic amine resin according to the above item [1], which is obtained by reacting an aniline compound substituted at the 2, 6-position with an alkylbenzaldehyde resin.
[3]
The aromatic amine resin according to the preceding item [1] or [2], which is represented by the following formula (2).
[ chemical 2]
(in the formula (2), n represents an average value, and 1+.n+.20).
[4]
The aromatic amine resin according to the preceding item [3], which is obtained by reacting 2-ethyl-6-methylaniline with a xylene formaldehyde resin.
[5]
The aromatic amine resin according to any one of the preceding items [1] to [4], which has a softening point of 80℃or lower.
[6]
The aromatic amine resin according to any one of the preceding items [1] to [5], which has a weight average molecular weight of 300 to 700.
[7]
A maleimide resin obtained by reacting the aromatic amine resin according to any of the preceding items [1] to [6] with maleic acid or maleic anhydride.
[8]
A curable resin composition comprising the maleimide resin according to the above item [7 ].
[9]
A cured product obtained by curing the curable resin composition according to item [8 ].
ADVANTAGEOUS EFFECTS OF INVENTION
The aromatic amine resin of the present invention has a sharp molecular weight distribution, and therefore is excellent in solvent solubility and handleability, and is also useful as a raw material for maleimide resins and the like.
The cured product of the curable resin composition containing the maleimide resin derived from the aromatic amine resin of the present invention has high heat resistance and excellent low dielectric characteristics, and is useful for sealing electric and electronic parts, circuit boards, carbon fiber composites, and the like.
Drawings
FIG. 1 shows a 1H-nuclear magnetic resonance (nuclear magnetic resonance, NMR) chart of example 1.
FIG. 2 shows a 1H-NMR chart of example 2.
Detailed Description
The aromatic amine resin of the present invention is represented by the following formula (1).
[ chemical 3]
(in the formula (1), R 1 、R 2 、R 3 Represents a hydrocarbon group having 1 to 18 carbon atoms. m represents an integer of 1 to 4, n represents an average value, and 1+.n+.20).
In the formula (1), R 1 、R 2 、R 3 The hydrocarbon group having 1 to 3 carbon atoms is preferable, and the hydrocarbon group having 1 or 2 carbon atoms is preferable.
The aromatic amine resin of the present invention is particularly preferably represented by the following formula (2).
[ chemical 4]
(in the formula (2), n represents an average value, and 1+.n+.20).
In addition, n is preferably 1+.n+.10, and more preferably 1+.n+.5.
The aromatic amine resin of the present invention has advantages in that the weight average molecular weight is not excessively large and the molecular weight distribution is sharp. The aromatic amine of the present invention has a sharp molecular weight distribution by using aniline having a substituent at the 2, 6-position as a raw material.
The weight average molecular weight of the aromatic amine of the present invention is preferably 300 to 700, and more preferably 400 to 600. The molecular weight distribution can be determined by gel permeation chromatography (gel permeation chromatography, GPC). In the case of synthesizing a maleimide resin from an amine resin having a weight average molecular weight of more than 700, it is difficult to purify the resin by washing with water and to remove impurities such as acid catalysts, because of the molecular weight and polarity. If the weight average molecular weight is less than 300, the solvent stability in the varnish may be lowered.
The method for producing the aromatic amine resin of the present invention is not particularly limited. For example, the 2, 6-substituted aniline compound may be reacted with an alkylbenzaldehyde (alkylbenzene formalin) resin in the presence of an acid catalyst such as hydrochloric acid or activated clay, or the 2, 6-substituted aniline compound, formaldehyde and alkylbenzenes may be reacted in the presence of an acid catalyst such as hydrochloric acid or activated clay. In the case of hydrochloric acid as a catalyst, the target aromatic amine resin can be obtained by neutralizing with an alkali metal such as sodium hydroxide or potassium hydroxide, extracting with an aromatic hydrocarbon solvent such as toluene or xylene, washing with water until the water discharge becomes neutral, and distilling off the solvent using an evaporator or the like.
Examples of the 2, 6-substituted aniline compound include 2, 6-dimethylaniline, 2, 6-diethylaniline, 2, 6-dipropylaniline, 2, 6-diisopropylaniline, 2-ethyl-6-methylaniline, 2-methyl-6-propylaniline, 2-isopropyl-6-methylaniline, 2-ethyl-6-propylaniline, 2-ethyl-6-isopropylaniline, and the like, but are not limited thereto. When the number of carbon atoms is large, the solvent solubility is improved, but the heat resistance is reduced, and therefore, the substitution with an alkyl group having 1 to 3 carbon atoms is preferable, the substitution with an alkyl group having 1 to 2 carbon atoms is more preferable, and 2-ethyl-6-methylaniline is most preferable.
Examples of the alkyl benzaldehyde resin include toluene formaldehyde resin, o-xylene formaldehyde resin, m-xylene formaldehyde resin, p-xylene formaldehyde resin, 1,2, 3-trimethyl benzaldehyde resin, 1,2, 4-trimethyl benzaldehyde resin, 1,2, 5-trimethyl benzaldehyde resin, 1,3, 5-trimethyl benzaldehyde resin, 1,2,3, 4-tetramethyl benzaldehyde resin, 1,2,3, 5-tetramethyl benzaldehyde resin, 1,2,4, 5-tetramethyl benzaldehyde resin, 1,3, 5-triethyl benzaldehyde resin, 1,3, 5-tripropyl benzaldehyde resin, 1,3, 5-triisopropyl benzaldehyde resin, 1,3, 5-tributyl benzaldehyde resin, 1,3, 5-tri-tert-butyl benzaldehyde resin and the like [ ], but are not limited thereto. These may be used alone or in combination of two or more. From the viewpoints of dielectric characteristics and heat resistance, the substitution with a hydrocarbon group having 1 to 5 carbon atoms is preferable, the substitution with a hydrocarbon group having 1 to 3 carbon atoms is more preferable, and the substitution with a methyl group is more preferable. As the carbon number of the hydrocarbon group increases, rigidity of the molecule is difficult to ensure, and the molecule is liable to vibrate, and therefore, the dielectric characteristics and heat resistance are lowered. The amount of the alkylbenzaldehyde resin used is usually 0.05 to 0.8% by weight, preferably 0.1 to 0.6% by weight, relative to 1% by weight of the aniline used.
When 2-ethyl-6-methylaniline is reacted with a xylene formaldehyde resin, if necessary, other lewis acids such as aluminum chloride and zinc chloride, solid acids such as activated clay, acid clay, white carbon, zeolite and silica alumina, acidic ion exchange resins and the like can be used in addition to hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, p-toluene sulfonic acid and methane sulfonic acid. These may be used alone or in combination of two or more. From the viewpoints of simplicity and economy of the production steps, it is preferable to use a reusable solid acid (solid acid such as activated clay, acid clay, white carbon, zeolite, silica alumina, or an acidic ion exchange resin). The amount of the catalyst to be used is usually 0.1 to 0.8 mol, preferably 0.2 to 0.7 mol, based on 1 mol of the 2, 6-substituted aniline compound to be used. If the amount of the solid acid is too large, the viscosity of the reaction solution may be too high, and if the amount of the solid acid catalyst is too small, the reaction may be slow (in the case of using the reusable solid acid catalyst, the amount of the 2, 6-substituted aniline compound to be charged is 1 to 50% by weight, preferably 5 to 40% by weight, more preferably 10 to 30% by weight). The reaction may be carried out using an organic solvent such as toluene or xylene, if necessary, or may be carried out in the absence of a solvent. For example, after adding an acidic catalyst to a mixed solution of a 2, 6-substituted aniline compound, an alkyl benzaldehyde resin and a solvent, when the catalyst contains water, water is removed from the system by azeotropic distillation. Then, the reaction is carried out at 40 to 180℃and preferably 50 to 170℃for 0.5 to 20 hours. Thereafter, the temperature is raised while removing water, low molecular weight components, etc. generated in the system by azeotropic dehydration, and the reaction is performed at 180 to 300 ℃, preferably 190 to 250 ℃, more preferably 200 to 240 ℃ for 5 to 50 hours, preferably 5 to 20 hours. After the completion of the reaction, the acidic catalyst is neutralized with an alkaline aqueous solution, a water-insoluble organic solvent is added to the oil layer, and washing with water is repeated until the wastewater becomes neutral (in the case of using the reusable solid acid catalyst, the catalyst is removed by filtration).
The aromatic amine resin of the present invention preferably has a softening point of 80℃or lower, more preferably 70℃or lower. If the softening point is higher than 80 ℃, the viscosity of the maleimided resin becomes high, and it is difficult to impregnate the carbon fiber or glass fiber. In the case of increasing the diluting solvent to reduce the viscosity, the resin may not adhere sufficiently to the fibrous material in the impregnation step.
The maleimide resin of the present invention is obtained by reacting maleic acid or maleic anhydride with the aromatic amine resin of the present invention in the presence of a solvent or a catalyst, and for example, the method described in Japanese patent publication No. 6429862 may be used. In this case, since it is necessary to remove water produced during the reaction from the system, a water-insoluble solvent is used as the solvent used for the reaction. Examples include: aromatic solvents such as toluene and xylene; aliphatic solvents such as cyclohexane and n-hexane; ethers such as diethyl ether and diisopropyl ether; ester solvents such as ethyl acetate and butyl acetate; ketone solvents such as methyl isobutyl ketone and cyclopentanone, etc., but the present invention is not limited thereto, and two or more kinds may be used in combination. In addition, an aprotic polar solvent may be used in addition to the water-insoluble solvent. Examples thereof include dimethylsulfone, dimethylsulfoxide, dimethylformamide, dimethylacetamide, 1, 3-dimethyl-2-imidazolidone, and N-methylpyrrolidone, and two or more of them may be used in combination. In the case of using an aprotic polar solvent, it is preferable to use an aprotic polar solvent having a boiling point higher than that of the water-insoluble solvent used in combination. The catalyst is not particularly limited, and examples thereof include acidic catalysts such as p-toluenesulfonic acid, hydroxy-p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, phosphoric acid and the like. For example, maleic acid is dissolved in toluene, the N-methylpyrrolidone solution of the aromatic amine resin of the present invention is added with stirring, and then p-toluenesulfonic acid is added thereto, and the reaction is performed while removing the water produced from the system under reflux conditions.
The curable resin composition of the present invention may be any conventional curable resin other than the maleimide resin of the present invention. Specifically, there may be mentioned: phenol resins, epoxy resins, amine resins, active olefin-containing resins, isocyanate resins, polyamide resins, polyimide resins, cyanate ester resins, acryl resins, methacrylic resins, active ester resins, and the like are preferably epoxy-containing resins, active olefin-containing resins, cyanate ester resins, and the like, in terms of balance of heat resistance, adhesion, and dielectric characteristics. By containing these curable resins, the brittleness of the cured product can be improved and the adhesion to metal can be improved, and cracking of the package during solder reflow or in reliability tests such as heat and cold cycles can be suppressed. The curable resin other than the maleimide resin of the present invention may be used alone or in combination of two or more.
The amount of the curable resin used is usually in the range of less than 10 mass times, preferably less than 3 mass times, more preferably less than 2 mass times, particularly preferably less than 1.5 mass parts, based on the maleimide resin of the present invention. When the mass ratio is 10 or more, the concentration of the maleimide resin of the present invention becomes low, and there is a possibility that sufficient heat resistance and dielectric characteristics cannot be obtained. The lower limit is preferably 0.2 times or more by mass, and more preferably 0.5 times or more by mass.
Phenol resin: polycondensates of phenols (phenol, alkyl-substituted phenol, aromatic-substituted phenol, hydroquinone, resorcinol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, dihydroxynaphthalene, etc.) with various aldehydes (formaldehyde, acetaldehyde, alkyl aldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthalene aldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde (cinnamaldehyde), furfural, etc.); polymers of phenols with various diene compounds (dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, isoprene, etc.); polycondensates of phenols with ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, etc.); phenol resins obtained by polycondensation of phenols with substituted biphenyls (4, 4 '-bis (chloromethyl) -1,1' -biphenyl, 4 '-bis (methoxymethyl) -1,1' -biphenyl, etc.), or substituted phenyls (1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene, 1, 4-bis (hydroxymethyl) benzene, etc.), etc.; polycondensates of bisphenols with various aldehydes; polyphenylene ether.
Epoxy resin: the phenol resin; glycidyl ether-based epoxy resins obtained by glycidylating alcohols and the like; alicyclic epoxy resins represented by 4-vinyl-1-cyclohexene diepoxide or 3, 4-epoxycyclohexylmethyl-3, 4' -epoxycyclohexane carboxylate; glycidyl amine-based epoxy resins represented by tetraglycidyl diaminodiphenylmethane (tetraglycidyl diamino diphenylmethane, TGDDM) or triglycidyl-p-aminophenol; glycidyl ester-based epoxy resins.
Amine resin: diaminodiphenyl methane; diamino diphenyl sulfone; isophorone diamine; naphthalene diamine; aniline novolac; o-ethylaniline novolac; an aniline resin obtained by reacting aniline with dichloroxylene (xylylene chloride); amine resins obtained by reacting aniline described in japanese patent No. 6429862 with substituted biphenyls (4, 4 '-bis (chloromethyl) -1,1' -biphenyl, 4 '-bis (methoxymethyl) -1,1' -biphenyl, etc.), or substituted phenyls (1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene, 1, 4-bis (hydroxymethyl) benzene, etc.).
Active olefin-containing resin: polycondensates of the above phenol resins with halogen compounds containing active olefins (chloromethylstyrene, allyl chloride, methallyl chloride, acryloyl chloride, etc.); polycondensates of phenols containing an active olefin (e.g., 2-allylphenol, 2-propenylphenol, 4-allylphenol, 4-propenylphenol, eugenol (eugenol), isoeugenol (isoeugenol), etc.) with a halogen compound (e.g., 4' -bis (methoxymethyl) -1,1' -biphenyl, 1, 4-bis (chloromethyl) benzene, 4' -difluorobenzophenone, 4' -dichlorobenzophenone, 4' -dibromobenzophenone, cyanuric chloride (cyanuric chloride); polycondensates of epoxy resins or alcohols with substituted or unsubstituted acrylic esters (acrylic esters, methacrylic esters, etc.); maleimide resins (4, 4' -diphenylmethane bismaleimide, polyphenylmethane maleimide, m-phenylene bismaleimide, 2' -bis [ 4- (4-maleimidophenoxy) phenyl ] propane, 3' -dimethyl-5, 5' -diethyl-4, 4' -diphenylmethane bismaleimide, 4-methyl-1, 3-phenylene bismaleimide, 4' -diphenyl ether bismaleimide, 4' -diphenyl sulfone bismaleimide, 1, 3-bis (3-maleimidophenoxy) benzene, 1, 3-bis (4-maleimidophenoxy) benzene).
Isocyanate resin: aromatic diisocyanates such as p-phenylene diisocyanate, m-phenylene diisocyanate, p-xylene diisocyanate, m-xylene diisocyanate, 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 4' -diphenylmethane diisocyanate, and naphthalene diisocyanate; aliphatic or alicyclic diisocyanates such as isophorone diisocyanate, hexamethylene diisocyanate, 4' -dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate, norbornene diisocyanate, and lysine diisocyanate; polyisocyanates such as one or more biurets of an isocyanate monomer or an isocyanate obtained by trimerizing the above-mentioned diisocyanate compound; a polyisocyanate obtained by a urethanization reaction of the isocyanate compound with a polyol compound.
Polyamide resin: with aliphatic diamines such as amino acids (6-aminocaproic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, and p-aminomethylbenzoic acid), lactams (ε -caprolactam, ω -undecanoic lactam, ω -laurolactam), alicyclic diamines such as diamine (ethylenediamine, trimethylene diamine, tetramethylenediamine, pentamethylene diamine, hexamethylene diamine, heptamethylene diamine, octamethylene diamine, nonamethylene diamine, decamethylene diamine, undecanediamine, dodecandiamine, tridecanediamine, tetradecanediamine, pentadecamethylene diamine, hexadecanediamine, heptadecanediamine, octadecanediamine, nonadecanediamine, eicosanediamine, 2-methyl-1, 5-diaminopentane, 2-methyl-1, 8-diaminooctane), alicyclic diamines such as cyclohexanediamine, bis- (4-aminocyclohexyl) methane, and aromatic diamines such as xylenediamine, with dicarboxylic acids (oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanediamine, dodecanediamine, 5-diaminopentane, 2-methyl-1, 8-diaminooctane, and 5-terephthalic acid, and 5-isophthalic acid, and terephthalic acid such as aliphatic terephthalic acid, and isophthalic acid, terephthalic acid and isophthalic acid, aromatic dicarboxylic acids such as hexahydroisophthalic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; dialkyl esters of these dicarboxylic acids and dichloride), and one or more of these dicarboxylic acids as a main raw material.
Polyimide resin: the diamine is mixed with tetracarboxylic dianhydride (4, 4'- (hexafluoroisopropylidene) diphthalic anhydride, 5- (2, 5-dioxotetrahydro-3-furyl) -3-methyl-cyclohexene-1, 2-dicarboxylic anhydride, pyromellitic dianhydride, 1,2,3, 4-benzene tetracarboxylic dianhydride, 3',4,4 '-benzophenone tetracarboxylic dianhydride, 2',3 '-benzophenone tetracarboxylic dianhydride, 3',4,4 '-biphenyltetracarboxylic dianhydride, 3',4 '-diphenylsulfone tetracarboxylic dianhydride, 2',3,3 '-biphenyltetracarboxylic dianhydride, methylene-4, 4' -diphthalic dianhydride, 1-ethylene-4, 4 '-diphthalic dianhydride, 2' -propylene-4, 4 '-diphthalic dianhydride, 1, 2-ethylene-4, 4' -diphthalic dianhydride, 1, 3-trimethylene-4, 4 '-diphthalic dianhydride, 1, 4-tetramethylene-4, 4' -diphthalic dianhydride, 1, 5-pentamethylene-4, 4 '-diphthalic dianhydride, 4' -oxydiphthalic dianhydride, thio-4, 4 '-diphthalic dianhydride, sulfonyl-4, 4' -diphthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenyl) phthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenoxy) phthalic dianhydride, 1, 4-bis (3, 4-dicarboxyphenoxy) phthalic dianhydride, 1, 3-bis [2- (3, 4-dicarboxyphenyl) -2-propyl ] benzene dianhydride, 1, 4-bis [2- (3, 4-dicarboxyphenyl) -2-propyl ] benzene dianhydride, bis [3- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, bis [4- (3, 4-dicarboxyphenoxy) phenyl ] methane dianhydride, 2-bis [3- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, 2-bis [4- (3, 4-dicarboxyphenoxy) phenyl ] propane dianhydride, bis (3, 4-dicarboxyphenoxy) dimethylsilane dianhydride 1, 3-bis (3, 4-dicarboxyphenyl) -1, 3-tetramethyldisiloxane dianhydride, 2,3,6, 7-naphthalene tetracarboxylic dianhydride, 1,4,5, 8-naphthalene tetracarboxylic dianhydride, 1,2,5, 6-naphthalene tetracarboxylic dianhydride, 3,4,9, 10-perylene tetracarboxylic dianhydride, 2,3,6, 7-anthracene tetracarboxylic dianhydride, 1,2,7, 8-phenanthrene tetracarboxylic dianhydride, ethylene tetracarboxylic dianhydride, 1,2,3, 4-butane tetracarboxylic dianhydride, 1,2,3, 4-cyclobutane tetracarboxylic dianhydride, cyclopentane tetracarboxylic dianhydride, cyclohexane-1, 2,3, 4-tetracarboxylic dianhydride, cyclohexane-1, 2,4, 5-tetracarboxylic dianhydride, 3 '; 4,4' -dicyclohexyltetracarboxylic dianhydride, carbonyl-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, methylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 1, 2-ethylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 1, 1-ethylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 2-propylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, oxy-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, thio-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, sulfonyl-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, bicyclo [2, 2] oct-7-ene-2, 3,5, 6-tetracarboxylic acid dianhydride, rel- [1S,5R,6R ] -3-oxabicyclo [3,2,1] octane-2, 4-dione-6-spiro-3 ' - (tetrahydrofuran-2 ',5' -dione), 4- (2, 5-dioxotetrahydrofuran-3-yl) -1,2,3, 4-tetrahydronaphthalene-1, 2-dicarboxylic anhydride, ethylene glycol-3- (4, 4-diphenyl) dicarboxylic acid anhydride, 4' -bis (diphenyl) dicarboxylic acid) dianhydride, and bis (diphenyl ether).
Cyanate resin: specific examples of the cyanate ester compound obtained by reacting a phenol resin with a cyanogen halide include: dicyanoxybenzene (dicyanoxybenzene), tricyanatobenzene, dicyanoxynaphthalene, dicyanoxybiphenyl, 2 '-bis (4-cyanoxyphenyl) propane, bis (4-cyanoxyphenyl) methane, bis (3, 5-dimethyl-4-cyanoxyphenyl) methane, 2' -bis (3, 5-dimethyl-4-cyanoxyphenyl) propane, 2 '-bis (4-cyanoxyphenyl) ethane, 2' -bis (4-cyanoxyphenyl) hexafluoropropane, bis (4-cyanoxyphenyl) sulfone, bis (4-cyanoxyphenyl) sulfide, phenol novolac cyanate, a cyanate group conversion of the hydroxyl group of the phenol-dicyclopentadiene cocondensate, and the like, but are not limited thereto.
Further, JP-A2005-264154 describes that a cyanate ester compound obtained by a synthesis method is particularly preferable as a cyanate ester compound because of low hygroscopicity, flame retardancy and excellent dielectric properties.
The cyanate ester resin may contain a catalyst such as zinc naphthenate, cobalt naphthenate, copper naphthenate, lead naphthenate, zinc octoate, tin octoate, lead acetylacetonate, and dibutyltin maleate, in order to trimerize the cyanate ester group to form a sym-triazine (sym-triazine) ring, if necessary. The catalyst is usually used in an amount of 0.0001 to 0.10 parts by mass, preferably 0.00015 to 0.0015 parts by mass, based on 100 parts by mass of the total thermosetting resin composition.
Active ester compound: if necessary, a compound having one or more active ester groups in one molecule may be used as a hardener for curable resins other than the essential components described in the present invention, such as epoxy resins. The active ester-based hardener is preferably a compound having two or more ester groups having high reactivity in one molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxyl compounds. The active ester-based hardener is preferably obtained by condensation reaction of at least one compound selected from a carboxylic acid compound and a thiocarboxylic acid compound with at least one compound selected from a hydroxyl compound and a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester-based hardener obtained from a carboxylic acid compound and a hydroxyl compound is preferable, and an active ester-based hardener obtained from a carboxylic acid compound and at least one compound selected from a phenol compound and a naphthol compound is preferable.
Examples of the carboxylic acid compound include: benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and the like.
Examples of the phenol compound or the naphthol compound include: hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, acid phenolphthalein, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, dicyclopentadiene type diphenol compounds, phenol novolac, and the like. The "dicyclopentadiene type diphenol compound" herein means a diphenol compound obtained by condensing phenol having two molecules in one molecule of dicyclopentadiene.
Preferable specific examples of the active ester-based hardener include an active ester compound containing a dicyclopentadiene type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetyl compound of phenol novolac, and an active ester compound containing a benzoyl compound of phenol novolac. Among them, an active ester compound containing a naphthalene structure and an active ester compound containing a dicyclopentadiene type diphenol structure are more preferable. The "dicyclopentadiene type diphenol structure" means a divalent structural unit containing phenylene-dicyclopentylene-phenylene.
Examples of commercial products of the active ester-based hardening agent include: "EXB9451", "EXB9460S", "HPC-8000-65T", "HPC-8000H-65TM", "EXB-8000L-65TM", "EXB-8150-65T" (manufactured by Dielsen (DIC)) as an active ester compound comprising a dicyclopentadiene type diphenol structure; "EXB9416-70BK" (manufactured by Dielsen (DIC)) as an active ester compound containing a naphthalene structure; "DC808" as an active ester compound comprising an acetyl compound of a phenol novolac (manufactured by Mitsubishi chemical corporation); "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi chemical corporation) as active ester compounds comprising benzoyl of phenol novolac; "DC808" as an active ester-based hardener which is an acetyl compound of phenol novolac (Mitsubishi chemical corporation); "EXB-9050L-62M" manufactured by Dielsen (DIC) Co., ltd.
In the curable resin composition of the present invention, a radical polymerization initiator is preferably used in order to promote the self-polymerization of a curable resin capable of radical polymerization such as a maleimide resin or the radical polymerization of other components. Examples of usable radical polymerization initiators include: ketone peroxides such as methyl ethyl ketone peroxide and acetylacetone peroxide; diacyl peroxides such as benzoyl peroxide; dialkyl peroxides such as dicumyl peroxide and 1, 3-bis (t-butylperoxyisopropyl) benzene; peroxy ketals such as t-butyl peroxybenzoate and 1, 1-di-t-butylperoxycyclohexane; alkyl peroxyacid esters such as α -cumyl peroxyneodecanoate, t-butyl peroxytrimethylacetate, 1, 3-tetramethylbutyl peroxy-2-ethylhexanoate, t-amyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-amyl peroxy-3, 5-trimethylhexanoate, t-butyl peroxy-3, 5-trimethylhexanoate, t-amyl peroxybenzoate; peroxycarbonates such as di-2-ethylhexyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxyisopropyl carbonate, and 1, 6-bis (t-butylperoxycarbonyloxy) hexane; conventional radical polymerization initiators such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyoctanoate, organic peroxides such as lauroyl peroxide, azobisisobutyronitrile, azo compounds such as 4,4 '-azobis (4-cyanovaleric acid) and 2,2' -azobis (2, 4-dimethylvaleronitrile), are not particularly limited thereto. Ketone peroxides, diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxy ketals, alkyl peroxy acid esters, peroxy carbonates, etc., are preferred, and dialkyl peroxides are more preferred. The amount of the radical polymerization initiator to be added is preferably 0.01 to 5 parts by mass, particularly preferably 0.01 to 3 parts by mass, based on 100 parts by mass of the curable resin composition. If the amount of the radical polymerization initiator used is large, the molecular weight cannot be sufficiently increased at the time of polymerization reaction.
In the curable resin composition of the present invention, a curing accelerator (curing catalyst) may be used in combination as needed. Specific examples of the hardening accelerator that can be used include: tertiary amines such as 2- (dimethylaminomethyl) phenol or 1, 8-diaza-bicyclo (5, 4, 0) undecene-7; phosphines such as triphenylphosphine; quaternary ammonium salts such as tetrabutylammonium salt, triisopropylmethyl ammonium salt, trimethyldecyl ammonium salt, cetyltrimethylammonium salt, and cetyltrimethylammonium hydroxide; quaternary phosphonium salts such as triphenylbenzyl phosphonium salt, triphenylethyl phosphonium salt and tetrabutylphosphonium salt (the counter ion of the quaternary phosphonium salt is halogen, organic acid ion, hydroxide ion, etc., and is not particularly limited, and particularly preferably a transition metal compound (transition metal salt) such as zinc compound such as zinc octoate, zinc carboxylate (zinc 2-ethylhexanoate, zinc stearate, zinc behenate, zinc myristate) or zinc phosphate (zinc octylphosphate, zinc stearyl phosphate, etc.), etc. The curing accelerator may be used in an amount of 0.01 to 5.0 parts by weight based on 100 parts by weight of the epoxy resin, as required.
The curable resin composition of the present invention may contain a phosphorus-containing compound as a flame retardancy-imparting material. The phosphorus-containing compound may be a reactive phosphorus-containing compound or an additive phosphorus-containing compound. Specific examples of the phosphorus-containing compound include: phosphates such as trimethyl phosphate, triethyl phosphate, trimethyl phenyl phosphate, tri (xylyl) phosphate, tolyl diphenyl phosphate, tolyl-2, 6-di (xylyl) phosphate, 1, 3-phenylenedi (di (xylyl) phosphate), 1, 4-phenylenedi (di (xylyl) phosphate), and 4,4' -biphenyl (di (xylyl) phosphate; phosphanes (phosphanes) such as 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide; the phosphorus-containing epoxy compound, red phosphorus, etc. obtained by reacting the epoxy resin with active hydrogen of the phosphane is preferably a phosphate, a phosphane or a phosphorus-containing epoxy compound, and particularly preferably 1, 3-phenylenedi (di (xylyl) phosphate), 1, 4-phenylenedi (di (xylyl) phosphate), 4' -biphenyl (di (xylyl) phosphate) or a phosphorus-containing epoxy compound. The content of the phosphorus-containing compound is preferably in the range of 0.1 to 0.6 (weight ratio) of (phosphorus-containing compound)/(total epoxy resin). If the flame retardance is 0.1 or less, the hygroscopicity of the cured product may be adversely affected, and if the flame retardance is 0.6 or more.
Further, an antioxidant may be added to the curable resin composition of the present invention as needed. Examples of antioxidants that can be used include phenol-based, sulfur-based, and phosphorus-based antioxidants. The antioxidant may be used singly or in combination of two or more. The amount of the antioxidant used is usually 0.008 to 1 part by weight, preferably 0.01 to 0.5 part by weight, based on 100 parts by weight of the resin component in the curable resin composition of the present invention. These antioxidants may be used alone or in combination of two or more. In the present invention, a phosphorus antioxidant is particularly preferable.
Specific examples of the phenolic antioxidants include: monophenols such as 2, 6-di-tert-butyl-p-cresol, butylated hydroxyanisole, 2, 6-di-tert-butyl-p-ethylphenol, stearyl- β - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, isooctyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, 2, 4-bis- (n-octylthio) -6- (4-hydroxy-3, 5-di-tert-butylaniline) -1,3, 5-triazine, 2, 4-bis [ (octylthio) methyl ] -o-cresol; 2,2' -methylenebis (4-methyl-6-tert-butylphenol), 2' -methylenebis (4-ethyl-6-tert-butylphenol), 4' -thiobis (3-methyl-6-tert-butylphenol), 4' -butylidenebis (3-methyl-6-tert-butylphenol), triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate ], 1, 6-hexanediol-bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], N, bisphenols such as N ' -hexamethylenebis (3, 5-di-tert-butyl-4-hydroxy-hydrocinnamamide), 2-thio-diethylenebis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], 3, 5-di-tert-butyl-4-hydroxybenzyl phosphate-diethyl ester, 3, 9-bis [1, 1-dimethyl-2- { β - (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy } ethyl ]2,4,8, 10-tetraoxaspiro [5,5] undecane, bis (3, 5-di-tert-butyl-4-hydroxybenzyl sulfonate) calcium; high molecular phenols such as 1, 3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, tetrakis [ methylene-3- (3 ',5' -di-tert-butyl-4 ' -hydroxyphenyl) propionate ] methane, ethylene bis [3,3' -bis- (4 ' -hydroxy-3 ' -tert-butylphenyl) butyrate, tris- (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, and 1,3, 5-tris (3 ',5' -di-tert-butyl-4 ' -hydroxybenzyl) -s-triazine-2, 4,6- (1H, 3H, 5H) trione, and tocopherol.
Specific examples of the sulfur-based antioxidant include dilauryl 3,3' -thiodipropionate, dimyristyl 3,3' -thiodipropionate, distearyl 3,3' -thiodipropionate, and the like.
Specific examples of the phosphorus antioxidant include: phosphites such as triphenyl phosphite, diphenylisodecyl phosphite, phenyldiisodecyl phosphite, tris (nonylphenyl) phosphite, pentaerythritol diisodecyl phosphite, tris (2, 4-di-t-butylphenyl) phosphite, cyclic neopentanetetrayl bis (octadecyl) phosphite, cyclic neopentanetetrayl bis (2, 4-di-t-butylphenyl) phosphite, cyclic neopentanetetrayl bis (2, 4-di-t-butyl-4-methylphenyl) phosphite, bis [ 2-t-butyl-6-methyl-4- {2- (octadecyloxycarbonyl) ethyl } phenyl ] halogenated phosphite; oxaphosphaphenanthrene oxides such as 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (3, 5-di-tert-butyl-4-hydroxybenzyl) -9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-decyloxy-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and the like.
Further, a light stabilizer may be added to the curable resin composition of the present invention as needed. The light stabilizer is preferably a hindered amine light stabilizer, and particularly preferably a hindered amine light stabilizer (Hindered Amine Light Stabilizer, HALS) or the like. The HALS is not particularly limited, and typical HALS include: dibutylamine 1,3, 5-triazine N, polycondensates of N' -bis (2, 6-tetramethyl-4-piperidinyl) -1, 6-hexamethylenediamine and N- (2, 6-tetramethyl-4-piperidinyl) butylamine, polycondensates of dimethyl-1- (2-hydroxyethyl) -4-hydroxy-2, 6-tetramethylpiperidine succinate poly- [ 6- (1, 3-tetramethylbutyl) amino-1, 3, 5-triazin-2, 4-diyl } { (2, 6-tetramethyl-4-piperidinyl) imino } hexamethylene{ (2, 6-tetramethyl-4-piperidinyl) imino } ], poly { (2, 6-tetramethyl } { (1, 3-tetramethylbutyl) amino-1, 3, 5-triazine-2, 4-diyl) -4-piperidinyl) imino } hexamethylene{ (2, 6-tetramethyl-4-piperidinyl) imino } ]. The HALS may be used alone or in combination of two or more.
Further, in the curable resin composition of the present invention, a binder resin may be formulated as needed. Examples of the binder resin include, but are not limited to, butyral resins, acetal resins, acrylic resins, epoxy-nylon resins, nitrile butadiene rubber (nitrile butadiene rubber, NBR) -phenol resins, epoxy-NBR resins, polyamide resins, polyimide resins, silicone resins, and the like. The amount of the binder resin to be blended is preferably in a range that does not impair the flame retardancy and heat resistance of the cured product, and is usually 0.05 to 50 parts by mass, preferably 0.05 to 20 parts by mass, per 100 parts by mass of the resin component, as required.
Further, if necessary, powders such as fused silica, crystalline silica, porous silica, alumina, zircon, calcium silicate, calcium carbonate, quartz powder, silicon carbide, silicon nitride, boron nitride, zirconia, aluminum nitride, graphite, forsterite (forsterite), steatite (spinel), mullite (mullite), titanium dioxide, talc (tac), clay, iron oxide, asbestos (ascestos), and glass powder, or spherical or crushed inorganic fillers thereof may be added to the curable resin composition of the present invention. In particular, in the case of obtaining a curable resin composition for semiconductor packaging, the amount of the inorganic filler used in the curable resin composition is usually in the range of 80 to 92 mass%, preferably 83 to 90 mass%.
In the curable resin composition of the present invention, conventional additives may be formulated as needed. Specific examples of the additive that can be used include polybutadiene and its modified products, modified products of acrylonitrile copolymers, polyphenylene ether, polystyrene, polyethylene, polyimide, fluororesin, silicone gel, silicone oil, a filler such as a silane coupling agent, a release agent, carbon black, phthalocyanine blue, phthalocyanine green, and other colorants. The blending amount of these additives is preferably 1,000 parts by mass or less, more preferably 700 parts by mass or less, per 100 parts by mass of the curable resin composition.
The curable resin composition of the present invention can be obtained by uniformly mixing the above-mentioned components in a predetermined ratio, and is usually pre-cured at 130 to 180℃for 30 to 500 seconds, and further post-cured at 150 to 200℃for 2 to 15 hours, whereby a sufficient curing reaction is performed to obtain the cured product of the present invention. In addition, the components of the curable resin composition may be uniformly dispersed or dissolved in a solvent or the like, and the solvent may be removed and cured.
The curable resin composition of the present invention obtained in the above manner has moisture resistance, heat resistance and high adhesion. Therefore, the curable resin composition of the present invention can be used in a wide range of fields where moisture resistance, heat resistance and high adhesion are required. Specifically, the composition is useful as a material for all electric and electronic parts such as an insulating material, a laminate (printed wiring board, ball Grid Array (BGA) substrate, build-up substrate, etc.), a sealing material, and a resist. In addition to molding materials and composite materials, the present invention can be used in fields such as coating materials and adhesives. Particularly in semiconductor encapsulation, solder reflow resistance is beneficial.
The semiconductor device is sealed by the curable resin composition of the present invention. Examples of the semiconductor device include: dual in-line package (DIP), quad flat package (quad flat package, QFP), ball Grid Array (BGA), chip scale package (chip size package, CSP), small outline package (small outline package, SOP), thin small outline package (thin small outline package, TSOP), thin quad flat package (thin quad flat package, TQFP), and the like.
The method for producing the curable resin composition of the present invention is not particularly limited, and the components may be uniformly mixed alone or may be converted into a prepolymer. For example, the curable resin of the present invention is heated in the presence or absence of a catalyst and in the presence or absence of a solvent, thereby performing prepolymer formation. Similarly, in addition to the curable resin of the present invention, a curing agent such as an epoxy resin, an amine compound, a maleimide compound, a cyanate ester compound, a phenol resin, and an acid anhydride compound, and other additives may be added to carry out the prepolymer. For mixing or prepolymer formation of each component, for example, an extruder, kneader, roll or the like is used in the absence of a solvent, and a reaction vessel or the like with a stirring device is used in the presence of a solvent.
As a method of uniformly mixing, a uniform resin composition is prepared by mixing at a temperature in the range of 50 to 100 ℃ using a kneading machine, a roll, a planetary mixer, or the like. The obtained resin composition may be molded into a cylindrical ingot by a molding machine such as a tablet machine after pulverization, or into a granular powder or a powdery molded body, or the composition may be melted on a surface support and molded into a sheet having a thickness of 0.05mm to 10mm to obtain a curable resin composition molded body. The obtained molded article is a molded article which is tack-free at 0 to 20 ℃, and has little deterioration in fluidity and hardenability even when stored at-25 to 0 ℃ for 1 week or more.
The molded article obtained can be molded into a cured product by a transfer molding machine or a compression molding machine.
An organic solvent may be added to the curable resin composition of the present invention to prepare a varnish-like composition (hereinafter referred to simply as varnish). The curable resin composition of the present invention can be prepared by dissolving the curable resin composition of the present invention in a solvent such as toluene, xylene, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethylformamide, dimethylacetamide, or N-methylpyrrolidone to prepare a varnish, impregnating the varnish with a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper, heating and drying the resultant prepreg, and hot-press-molding the resultant prepreg. The solvent used in this case is usually used in an amount of 10 to 70% by weight, preferably 15 to 70% by weight, based on the mixture of the curable resin composition of the present invention and the solvent. In addition, in the case of a liquid composition, a cured resin containing carbon fibers may be obtained directly by, for example, resin transfer molding (resin transfer molding, RTM).
The curable composition of the present invention can also be used as a modifier for film compositions. Specifically, the method can be used for improving the flexibility of the B-stage. Such a film-type resin composition is obtained by preparing the curable resin composition of the present invention into the curable resin composition varnish, applying the curable resin composition varnish onto a release film, removing the solvent under heating, and then subjecting the resultant film to B-staging. The sheet-like adhesive can be used as an interlayer insulating layer of a multilayer substrate or the like.
The curable resin composition of the present invention can be heat-melted and reduced in viscosity to impregnate reinforcing fibers such as glass fibers, carbon fibers, polyester fibers, polyamide fibers, and alumina fibers, thereby obtaining a prepreg. Specific examples thereof include glass fibers such as E glass cloth, D glass cloth, S glass cloth, Q glass cloth, spherical glass cloth, NE glass cloth, and T glass cloth, and further include fibers of inorganic substances other than glass, poly (paraphenylene terephthalamide) (polyparaphenylene terephthalamide) (kevlar) (registered trademark), manufactured by Dupont (Dupont), wholly aromatic polyamide, and polyester; and organic fibers such as polyparaphenylene benzobisoxazole (polyparaphenylene benzoxazole), polyimide, and carbon fibers, but are not particularly limited thereto. The shape of the base material is not particularly limited, and examples thereof include woven fabric, nonwoven fabric, roving (winding), and chopped strand mat (chopped strand mat). As a weaving method of the woven fabric, a plain weave, a basket weave (basket weave), a twill weave (twill weave), or the like is known, and may be used as appropriate depending on the intended use or performance from among these conventional weaving methods. In addition, a glass fabric having a fabric subjected to a fiber opening treatment or a surface treatment with a silane coupling agent or the like is preferably used. The thickness of the base material is not particularly limited, but is preferably about 0.01mm to 0.4 mm. The prepreg may be obtained by impregnating the reinforcing fiber with the varnish and drying the impregnated reinforcing fiber by heating.
The laminated board of the present embodiment includes one or more prepregs. The laminate is not particularly limited as long as it is a laminate including one or more prepregs, and may have any other layers. As a method for producing the laminated board, a general conventional method can be suitably applied, and is not particularly limited. For example, in the case of molding a laminate sheet on which a metal foil is attached, a multi-stage press, a multi-stage vacuum press, a continuous molding machine, an autoclave molding machine, or the like may be used, and the laminate sheet may be obtained by laminating the prepregs to each other and performing heat and pressure molding. In this case, the heating temperature is not particularly limited, but is preferably 65℃to 300℃and more preferably 120℃to 270 ℃. The pressure of the pressurization is not particularly limited, but if the pressurization is too large, the solid content of the resin of the laminate is difficult to adjust, and the quality is unstable, and if the pressure is too small, the adhesiveness between the bubbles and the laminate is deteriorated, so that it is preferably 2.0MPa to 5.0MPa, more preferably 2.5MPa to 4.0MPa. The laminated sheet of the present embodiment can be preferably used as a laminated sheet with a metal foil, which will be described later, by including a layer with a metal foil.
The prepreg is cut into a desired shape, and if necessary, laminated with copper foil or the like, and then the curable resin composition is cured by heating while applying pressure to the laminate by press molding, autoclave molding, sheet winding molding, or the like, whereby a laminate for electric and electronic use (printed wiring board) or a carbon fiber reinforcement can be obtained.
The cured product of the present invention can be used for various applications such as molding materials, adhesives, composite materials, and paints. The cured product of the curable resin composition of the present invention exhibits excellent heat resistance and dielectric characteristics, and is therefore preferably used in a sealing material for semiconductor elements, a sealing material for liquid crystal display elements, a sealing material for organic Electroluminescence (EL) elements, an electrical/electronic component such as a printed wiring board or a laminate, or a composite material for lightweight high-strength structural materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics.
Examples
The present invention will be described more specifically with reference to examples. Hereinafter, unless otherwise indicated, parts are parts by weight. Furthermore, the present invention is not limited to these examples.
Various analysis methods used in examples are described below.
< amine equivalent >)
The obtained value was taken as an amine equivalent according to Japanese Industrial Standard (Japanese Industrial Standards, JIS) K-7236 annex A (correction method for glycidylamine).
< softening Point >)
The measurement was carried out in accordance with JIS K-7234.
< ICI viscosity (150 ℃ C.) >
The measurement was carried out in accordance with JIS K-7117-2.
Weight average molecular weight (Mw) >
The calculation was performed by conversion of polystyrene using a polystyrene standard solution.
Gel permeation chromatograph (gel permeation chromatograph, GPC): DGU-20A3R, LC-20AD, SIL-20AHT, RID-20A, SPD-20A, CTO-20A, CBM-20A (all manufactured by Shimadzu corporation)
And (3) pipe column: sodex KF-603, KF-602×2, KF-601×2
Connecting the eluent: tetrahydrofuran (THF)
Flow rate: 0.5ml/min.
Column temperature: 40 DEG C
A detector: RI (refractive index) (differential refractive detector)
Example 1
A flask equipped with a thermometer, a cooling tube, a Dean-Stark (Dean-Stark) azeotropic distillation trap, and a stirrer was charged with 198 parts of xylene formaldehyde resin (nicanol (NIKANOL) G, fudow (Fudow) Co., ltd.), 622 parts of 2-ethyl-6-methylaniline (Tokyo Co., ltd.) and 300 parts of toluene, 82 parts of activated clay (Kanji Co., ltd.) and reacted at 120℃for 1 hour, and then the distillate was extracted and heated to 150℃for 4 hours. Thereafter, the temperature was raised to 200℃and the reaction was carried out at 200℃for 10 hours. After cooling, the mixture was diluted with 300 parts of toluene, and after removal of activated clay by filtration, 315 parts of an aromatic amine resin (A1) (softening point: 65 ℃ C., melt viscosity: 0.13 Pa.s, amine equivalent: 199g/eq, mw: 581) was obtained by distilling off the solvent and excess 2-ethyl-6-methylaniline under reduced pressure and heating. The 1H-NM R chart of the obtained amine resin is shown in FIG. 1.
1H-NMR (400 MHz, dimethyl sulfoxide (DMSO) -d 6): delta (ppm) 0.92-1.18 (m, 221H), 1.88-2.46 (m, 611H), 3.48-3.98 (m, 124H), 4.21-4.38 (m, 127H), 5.33 (s, 4H), 6.30-6.70 (m, 156H), 6.82-7.02 (m, 35H), 7.23 (s, 4H)
Example 2
221 parts of maleic anhydride (manufactured by tokyo chemical Co., ltd.) and 100 parts of toluene were charged into a flask equipped with a thermometer, a cooling tube, a dean-Stark azeotropic distillation trap, and a stirrer, and water and toluene azeotroped by heating were cooled and separated, and then only toluene as an organic layer was returned to the system to be dehydrated. Then, 300 parts of the aromatic amine resin (A1) obtained in example 1 was dissolved in a mixed solvent of 50 parts of N-methyl-2-pyrrolidone and 150 parts of toluene to obtain a resin solution, and the obtained resin solution was added dropwise over 1 hour while keeping the temperature in the system at 80 to 85 ℃. After the completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours, 6 parts of p-toluenesulfonic acid was added, and after azeotropic condensation water and toluene were cooled and separated under reflux, only toluene as an organic layer was returned to the system to be dehydrated, and the reaction was carried out for 20 hours. After completion of the reaction, 600 parts of toluene was added, and the mixture was repeatedly washed with water to remove p-toluene sulfonic acid and excess maleic anhydride, and then heated to remove water from the system by azeotropy. Then, the reaction solution was concentrated to obtain a resin solution containing 70% by weight of maleimide resin (M1). The maleimide resin (M1) had a weight average molecular weight (Mw) of 827. The 1H-NMM R diagram of the maleimide resin (M1 ') obtained by concentrating under reduced pressure to obtain the maleimide resin (M1') as a solid is shown in FIG. 2.
1H-NMR(400MHz,DMSO-d6):δ(ppm)0.80-1.10(m,7H),1.75-2.40(m,20H),3.61-4.28(m,4H),6.59-7.18(m,6H),7.25(d,4H)
Comparative example 1
A flask equipped with a thermometer, a cooling tube, a dean Stark azeotropic distillation trap and a stirrer was charged with 210 parts of xylene formaldehyde resin (Nikanol G, fudow (Fudow) Co., ltd.), 738 parts of aniline (Tokyo chemical Co., ltd.), 100 parts of toluene and 95 parts of activated clay, and the mixture was reacted at 120℃for 1 hour, and then the distillate was extracted and heated to 150℃for 4 hours. Thereafter, the temperature was raised to 200℃and the reaction was carried out at 200℃for 10 hours. After cooling, 300 parts of toluene was used for dilution, activated clay (manufactured by activated clay Co., ltd.) was removed by filtration, and then the solvent and excess aniline were distilled off under reduced pressure and heating, whereby 314 parts of an aromatic amine resin (A2) (softening point: 66.6 ℃ C., melt viscosity: 0.23 Pa.s, amine equivalent: 198g/eq, mw: 734) was obtained.
Comparative example 2
186 parts of maleic anhydride (manufactured by tokyo chemical Co., ltd.) and 250 parts of toluene were charged into a flask equipped with a thermometer, a cooling tube, a dean-Stark azeotropic distillation trap, and a stirrer, and water and toluene azeotroped by heating were cooled and separated, and then only toluene as an organic layer was returned to the system to be dehydrated. Next, 250 parts of the aromatic amine resin (A2) obtained in comparative example 1 was dissolved in a mixed solvent of 250 parts of N-methyl-2-pyrrolidone and 250 parts of toluene to obtain a resin solution, and the obtained resin solution was added dropwise over 1 hour while maintaining the temperature in the system at 80 to 85 ℃. After completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours, 5 parts of p-toluenesulfonic acid (manufactured by tokyo chemical Co., ltd.) was added, and after cooling and separating azeotropic condensed water and toluene under reflux conditions, only toluene as an organic layer was returned to the system to be dehydrated, and the reaction was carried out for 20 hours. After completion of the reaction, 500 parts of toluene was added, and washing was performed, and as a result, the mixture was separated into three layers during the liquid separation, and extraction was impossible.
Comparative example 3
After completion of the reaction, 3000 parts of toluene and 300 parts of N-methyl-2-pyrrolidone were added, and the reaction was repeatedly washed with water to remove p-toluenesulfonic acid and excess maleic anhydride, and then heated to remove water from the system by azeotropy. Then, the reaction solution was concentrated to obtain a resin solution containing 70% by weight of maleimide resin (M2). The maleimide resin (M2) has a weight average molecular weight (Mw) of 1204.
It was confirmed that the aromatic amine resin (A1) obtained in example 1 had a smaller weight average molecular weight and a sharp molecular weight distribution than the aromatic amine resin (A2) obtained in comparative example 2. Since the weight average molecular weight of the aromatic amine resin (A2) exceeds 700, the maleimide resin (M2) obtained from the aromatic amine resin (A2) is difficult to purify by ordinary water washing as shown in comparative example 2 due to the size of the molecular weight and the polarity thereof, and impurities such as acid catalyst cannot be removed. As shown in comparative example 3, the maleimide resin (M2) was not washed with water without using a large amount of an organic solvent and a high-polarity and high-boiling point solvent. Therefore, there is a problem that a high boiling point solvent remains in the maleimide resin, and the aromatic amine resin (A1) is excellent in terms of reduction of industrial waste, improvement of the amount of obtained in the same facility, simplification of the production steps, and the like.
[ example 3, comparative example 4, comparative example 5]
The maleimide compound (M1'), BMI-2300 obtained in example 2, was prepared in the proportions (parts by mass) shown in table 1, and was taken out as a solid by concentration under reduced pressure: aniline novolac type maleimide compound (manufactured by large and chemical industry Co., ltd.), biphenyl aralkyl type epoxy resin (NC-3000-L manufactured by Japanese chemical Co., ltd.), biphenyl aralkyl type phenol resin (Kayahard (manufactured by Kayahard) GPH-65, manufactured by Japanese chemical Co., ltd.), 2E-4MZ (2-ethyl-4-methylimidazole manufactured by four chemical Co., ltd.) as a hardening accelerator, and heat and melt mixed in a metal container, directly poured into a mold, and hardened at 220℃for 2 hours.
Example 4
The maleimide compound (M1') obtained in example 2 and dicumyl peroxide (manufactured by Kayaku Akzo) were prepared in the proportions (parts by mass) shown in table 1, concentrated under reduced pressure, taken out as a solid, heated and melt-mixed in a metal container, poured directly into a mold, and cured at 220 ℃ for 2 hours.
The results of measuring the physical properties of the cured product obtained in the above manner are shown in table 1.
< Heat resistance test >)
Glass transition temperature: the temperature at which tan delta is the maximum value was measured by a dynamic viscoelasticity tester.
Dynamic viscoelasticity tester: DMA-2980 manufactured by TA instruments (TA-instruments)
Heating rate: 2 ℃/min
Dielectric constant test and dielectric loss tangent test
The test was performed using a cavity resonator perturbation method using a 1GHz cavity resonator manufactured by kanto electronics application development (stock). The test was performed with a sample size of 1.7mm wide by 100mm long and a thickness of 1.7 mm.
TABLE 1
M1': the maleimide resin was obtained by removing the solvent by distillation under reduced pressure and heat as described in example 2
BMI-2300: aniline novolac type maleimide compound (manufactured by Dahe chemical industry Co., ltd.)
DCP: dicumyl peroxide (manufactured by chemical drug Account Su Co., ltd.)
NC-3000-L: biphenyl aralkyl type epoxy resin (manufactured by Japanese chemical Co., ltd.)
GPH-65: biphenyl aralkyl phenol resin (manufactured by Japanese chemical Co., ltd.)
2E-4MZ: 2-ethyl-4-methylimidazole (manufactured by four kingdoms chemical Co., ltd.)
From table 1, it was confirmed that example 3 and example 4 had high heat resistance and excellent dielectric characteristics.
Industrial applicability
The curable resin composition of the present invention is useful for various applications such as composite materials and paints including insulating materials for electric and electronic parts (high-reliability semiconductor sealing materials, etc.), laminated boards (printed wiring boards, BGA substrates, build-up boards, etc.), adhesives (conductive adhesives, etc.), and carbon fiber reinforced plastics (carbon fiber reinforced plastic, CFRP).
Claims (10)
1. A maleimide resin obtained by reacting an aromatic amine resin represented by the following formula (1) with maleic acid or maleic anhydride:
in the formula (1), R 1 Is ethyl, R 2 Is methyl, R 3 Is methyl; m represents an integer of 1 to 4, n represents an average value, and 1+.n+.20.
2. The maleimide resin according to claim 1, wherein the aromatic amine resin represented by the formula (1) is an aromatic amine resin obtained by reacting an aniline compound substituted in the 2, 6-position with an alkylbenzaldehyde resin.
3. The maleimide resin according to claim 1, wherein the aromatic amine resin represented by the formula (1) has a softening point of 80 ℃ or lower.
4. The maleimide resin according to claim 1, wherein the aromatic amine resin represented by the formula (1) has a weight average molecular weight of 300 to 700.
5. A maleimide resin obtained by reacting an aromatic amine resin represented by the following formula (2) with maleic acid or maleic anhydride:
in the formula (2), n represents an average value, and 1+.n+.20.
6. The maleimide resin according to claim 5, wherein the aromatic amine resin represented by the formula (2) is an aromatic amine resin obtained by reacting 2-ethyl-6-methylaniline with a xylene formaldehyde resin.
7. The maleimide resin according to claim 5, wherein the aromatic amine resin represented by the formula (2) has a softening point of 80 ℃ or lower.
8. The maleimide resin according to claim 5, wherein the aromatic amine resin represented by the formula (2) has a weight average molecular weight of 300 to 700.
9. A curable resin composition comprising the maleimide resin according to any one of claims 1 to 8.
10. A cured product obtained by curing the curable resin composition according to claim 9.
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JP2003146970A (en) * | 2001-11-12 | 2003-05-21 | Mitsui Chemicals Inc | Method of producing maleimide |
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