CN113260646A - 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
- CN113260646A CN113260646A CN202080007530.2A CN202080007530A CN113260646A CN 113260646 A CN113260646 A CN 113260646A CN 202080007530 A CN202080007530 A CN 202080007530A CN 113260646 A CN113260646 A CN 113260646A
- Authority
- CN
- China
- Prior art keywords
- resin
- aromatic amine
- acid
- bis
- dianhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 140
- 239000011347 resin Substances 0.000 title claims abstract description 140
- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 44
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- -1 aniline compound Chemical group 0.000 claims description 94
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 25
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-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 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 27
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007789 sealing Methods 0.000 abstract description 3
- 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 31
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000047 product Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 15
- 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
- 229910052698 phosphorus Inorganic materials 0.000 description 14
- 239000000243 solution Substances 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
- 239000011574 phosphorus Substances 0.000 description 13
- 239000004927 clay Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000010438 heat treatment Methods 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
- 150000001412 amines Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000000203 mixture Substances 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
- 239000003963 antioxidant agent Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000004643 cyanate ester Substances 0.000 description 9
- 238000000034 method Methods 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
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 7
- 238000010533 azeotropic distillation Methods 0.000 description 7
- 239000004744 fabric Substances 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
- 238000005406 washing Methods 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
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 239000004917 carbon fiber Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000011973 solid acid Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-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
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 4
- 238000000576 coating method Methods 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
- 239000003365 glass fiber Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
- 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 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 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- 238000001914 filtration Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 3
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
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- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical compound COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 description 2
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- MODAACUAXYPNJH-UHFFFAOYSA-N 1-(methoxymethyl)-4-[4-(methoxymethyl)phenyl]benzene Chemical group C1=CC(COC)=CC=C1C1=CC=C(COC)C=C1 MODAACUAXYPNJH-UHFFFAOYSA-N 0.000 description 2
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- 238000005821 Claisen rearrangement reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 239000004642 Polyimide Substances 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 230000003472 neutralizing effect Effects 0.000 description 1
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- 239000004745 nonwoven fabric Substances 0.000 description 1
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
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- 229960001553 phloroglucinol Drugs 0.000 description 1
- YSWYYGKGAYSAOJ-UHFFFAOYSA-N phosphane Chemical class P.P YSWYYGKGAYSAOJ-UHFFFAOYSA-N 0.000 description 1
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- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
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- 125000004437 phosphorous atom Chemical group 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 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
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 125000006158 tetracarboxylic acid group Chemical group 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
- 238000005382 thermal cycling Methods 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
- 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
- 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
- XJIAZXYLMDIWLU-UHFFFAOYSA-N undecane-1,1-diamine Chemical compound CCCCCCCCCCC(N)N XJIAZXYLMDIWLU-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
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-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
Images
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
Abstract
The purpose of the present invention is to provide an aromatic amine resin having a specific structure and excellent solvent solubility. Further, an object of the present invention is to provide a curable resin composition which can be preferably used for sealing of electric and electronic components, circuit boards, carbon fiber composites, and the like, has high heat resistance and excellent low dielectric characteristics, and contains a maleimide resin derived from an aromatic amine having a specific structure, and a cured product thereof. An aromatic amine resin represented by the following formula (1). In the formula (1), R1, R2 and R3 represent 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, which are preferably used for electric and electronic components such as semiconductor sealing materials, printed wiring boards, build-up laminates, and lightweight high-strength materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics.
Background
In recent years, a laminate board on which electric and electronic components are mounted has been required to have a wide range of characteristics and a high degree of height due to expansion of the field of use thereof. A conventional semiconductor chip is mainly mounted on a metal lead frame, but a semiconductor chip having high processing capability such as a Central Processing Unit (CPU) is often mounted on a laminate made of a polymer material.
In particular, in a semiconductor package (package) used in a smart phone or the like (hereinafter, referred to as PKG), thinning of a PKG substrate is required in order to meet the demand for miniaturization, thinning, and high density, but since the rigidity is lowered when the PKG substrate is thinned, heating when the PKG is solder-mounted on a motherboard (printed circuit board) causes a problem such as a large warp. To reduce the above, a high Tg PKG substrate material above the solder mounting temperature is required.
Further, the fifth generation communication system "5G" which is currently under accelerated development is expected to further advance the increase in capacity and high-speed communication. The demand for low dielectric loss tangent materials is increasing, and dielectric loss tangent of 0.005 or less at 1GHz is required at least.
Further, in the automobile field, electronics is advancing, and since precise electronic equipment is sometimes disposed near an engine drive portion, a higher level of heat resistance and moisture resistance is required. SiC semiconductors have been used in electric vehicles, air conditioners, and the like, and since extremely high heat resistance is required for sealing materials for semiconductor elements, conventional epoxy resin sealing materials have become incompatible.
Under such a background, a polymer material having both heat resistance and low dielectric loss tangent has been studied. For example, patent document 1 proposes a composition containing a maleimide resin and an acryl-containing phenol resin. However, on the other hand, the phenolic hydroxyl group which does not participate in the reaction remains during the curing reaction, and therefore the electrical characteristics are not sufficient. Patent document 2 discloses an allyl ether resin in which a hydroxyl group is substituted with an allyl group. However, it was revealed that Claisen Rearrangement (Claisen Rearrangement) occurs at 190 ℃ and phenolic hydroxyl groups which do not contribute to the curing reaction are generated at 200 ℃ which is the molding temperature of a general substrate, and thus electrical characteristics cannot be satisfied.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. H04-359911
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.
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, they have 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 have completed the present invention.
That is, the present invention relates to the following [1] to [9 ].
[1]
An aromatic amine resin represented by the following formula (1).
[ solution 1]
(in the formula (1), R1, R2 and R3 represent 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 above item [1] or [2], which is represented by the following formula (2).
[ solution 2]
(in the formula (2), n represents an average value, and 1 ≦ n ≦ 20).
[4]
The aromatic amine resin according to the above 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 one 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 ].
[ Effect of the invention ]
The aromatic amine resin of the present invention has a sharp molecular weight distribution, and therefore has excellent solvent solubility and handling properties, and is also very 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 components, circuit boards, carbon fiber composites, and the like.
Drawings
FIG. 1 shows a 1H-Nuclear Magnetic Resonance (NMR) chart of example 1.
FIG. 2 is a chart showing 1H-NMR of example 2.
Detailed Description
The aromatic amine resin of the present invention is represented by the following formula (1).
[ solution 3]
(in the formula (1), R1, R2 and R3 represent 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), R1, R2 and R3 are preferably hydrocarbon groups having 1 to 3 carbon atoms, and m is preferably 1 or 2.
The aromatic amine resin of the present invention is particularly preferred when it is represented by the following formula (2).
[ solution 4]
(in the formula (2), n represents an average value, and 1 ≦ n ≦ 20).
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 starting 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 measured by Gel Permeation Chromatography (GPC). When a maleimide resin is synthesized 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 an acid catalyst because of the high molecular weight and the low 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 (alkylbenzaldehyde) resin in the presence of an acid catalyst such as hydrochloric acid or activated clay, or the 2, 6-substituted aniline compound, formaldehyde and alkylbenzene may be reacted in the presence of an acid catalyst such as hydrochloric acid or activated clay. When hydrochloric acid is used 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 drainage becomes neutral, and distilling off the solvent using an evaporator or the like.
Examples of the aniline compound substituted at the 2, 6-position include, but are not limited to, 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, and 2-ethyl-6-isopropylaniline. When the carbon number is large, the solvent solubility is improved, but the heat resistance is lowered, so that the alkyl group having 1 to 3 carbon atoms is preferably substituted, more preferably substituted by the alkyl group having 1 to 2 carbon atoms, and most preferably 2-ethyl-6-methylaniline.
Examples of the alkylbenzaldehyde resin include toluene formaldehyde resin, o-xylene formaldehyde resin, m-xylene formaldehyde resin, p-xylene formaldehyde resin, 1,2, 3-trimethylbenzaldehyde resin, 1,2, 4-trimethylbenzaldehyde resin, 1,2, 5-trimethylbenzaldehyde resin, 1,3, 5-trimethylbenzaldehyde resin, 1,2,3, 4-tetramethylbenzaldehyde resin, 1,2,3, 5-tetramethylbenzaldehyde resin, 1,2,4, 5-tetramethylbenzaldehyde resin, 1,3, 5-triethylbenzaldehyde resin, 1,3, 5-tripropylbenzaldehyde resin, 1,3, 5-triisopropylbenzaldehyde resin, 1,3, 5-tributylbenzaldehyde resin, 1,3, 5-tri-t-butylbenzaldehyde resin and the like [, but is not limited thereto. These may be used alone or in combination of two or more. From the viewpoint of dielectric properties and heat resistance, the compound is preferably substituted with a hydrocarbon group having 1 to 5 carbon atoms, more preferably substituted with a hydrocarbon group having 1 to 3 carbon atoms, and even more preferably substituted with a methyl group. As the number of carbon atoms in the hydrocarbon group increases, rigidity of the molecule is hard to be secured, and the molecule is likely to vibrate, which causes a decrease in dielectric properties and heat resistance. The amount of the alkylbenzaldehyde resin used is usually 0.05 to 0.8% by weight, preferably 0.1 to 0.6% by weight, based on 1% by weight of the aniline used.
When 2-ethyl-6-methylaniline is reacted with xylene formaldehyde resin, as required, in addition to hydrochloric acid, phosphoric acid, sulfuric acid, formic acid, p-toluenesulfonic acid and methanesulfonic acid, Lewis acids such as aluminum chloride and zinc chloride, solid acids such as activated clay, acid clay, white carbon, zeolite and silica alumina, and acidic ion exchange resins are exemplified. These may be used alone or in combination of two or more. From the viewpoint of simplicity of the production process and economy, it is preferable to use a reusable solid acid (a 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 aniline compound substituted at the 2, 6-position used. If the amount is too large, the viscosity of the reaction solution becomes too high, and stirring may become difficult, and if the amount is too small, the reaction may progress slowly (in the case of using the reusable solid acid catalyst, the amount is 1 to 50 wt%, preferably 5 to 40 wt%, and more preferably 10 to 30 wt% relative to the amount of the charged 2, 6-substituted aniline compound. The reaction may be carried out using an organic solvent such as toluene or xylene as required, or may be carried out without a solvent. For example, after an acidic catalyst is added to a mixed solution of an aniline compound substituted at the 2, 6-position, an alkylbenzaldehyde resin and a solvent, water is removed from the system by azeotropic distillation when the catalyst contains water. Then, the reaction is carried out at 40 to 180 ℃ and preferably 50 to 170 ℃ for 0.5 to 20 hours. Thereafter, while removing water, low molecular weight components, and the like generated in the system by azeotropic dehydration, the temperature is raised, and the reaction is carried out 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 reaction is completed, the acidic catalyst is neutralized with an alkaline aqueous solution, and then a water-insoluble organic solvent is added to the oil layer, and washing with water is repeated until the waste water becomes neutral (in the case of using the reusable solid acid catalyst, the catalyst is removed by filtration).
The softening point of the aromatic amine resin of the present invention is preferably 80 ℃ or lower, more preferably 70 ℃ or lower. If the softening point is higher than 80 ℃, the viscosity of the maleimide-based resin increases, and impregnation into carbon fibers or glass fibers becomes difficult. When the viscosity is reduced by increasing the dilution solvent, the resin may not sufficiently adhere to the fibrous material in the impregnation step.
The maleimide resin of the present invention is obtained by reacting the aromatic amine resin of the present invention with maleic acid or maleic anhydride in the presence of a solvent and a catalyst, and for example, the method described in japanese patent No. 6429862 may be used. In this case, since it is necessary to remove water generated in the reaction from the system, a water-insoluble solvent is used as the solvent used in the reaction. Examples thereof 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, but the solvent is not limited thereto, and two or more kinds thereof may be used in combination. Besides the water-insoluble solvent, an aprotic polar solvent may be used in combination. Examples thereof include dimethyl sulfone, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1, 3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone, and two or more of them may be used in combination. When an aprotic polar solvent is used, it is preferable to use an aprotic polar solvent having a higher boiling point than the water-insoluble solvent used in combination. The catalyst is not particularly limited, and acidic catalysts such as p-toluenesulfonic acid, hydroxy-p-toluenesulfonic acid, methanesulfonic acid, sulfuric acid, phosphoric acid and the like can be mentioned. For example, maleic acid is dissolved in toluene, an N-methylpyrrolidone solution of the aromatic amine resin of the present invention is added under stirring, p-toluenesulfonic acid is then added, and the reaction is carried out while removing the produced water from the system under reflux conditions.
Any conventional curable resin can be used as the curable resin composition of the present invention, except 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, and in terms of the balance among heat resistance, adhesiveness, and dielectric properties, epoxy resins, active olefin-containing resins, and cyanate ester resins are preferably contained. By containing these curable resins, the brittleness of the cured product can be improved, the adhesion to metal can be improved, and cracks in the package during reliability tests such as solder reflow and thermal cycling can be suppressed. One or more kinds of curable resins other than the maleimide resin of the present invention may be used.
The amount of the curable resin used is generally in a mass range of less than 10 times by mass, preferably less than 3 times by mass, more preferably less than 2 times by mass, and particularly preferably less than 1.5 parts by mass relative to the maleimide resin of the present invention. When the amount is 10 times by mass or more, the concentration of the maleimide resin of the present invention may be low, and sufficient heat resistance and dielectric properties may not be obtained. The lower limit is preferably 0.2 times by mass or more, and more preferably 0.5 times by mass or more.
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, naphthaldehyde, 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 (e.g., 4 '-bis (chloromethyl) -1,1' -biphenyl and 4,4 '-bis (methoxymethyl) -1,1' -biphenyl), or substituted phenyls (e.g., 1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene and 1, 4-bis (hydroxymethyl) benzene); 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, 3, 4-epoxycyclohexylmethyl-3, 4' -epoxycyclohexanecarboxylate, and the like; glycidyl amine epoxy resins typified by tetraglycidyl diaminodiphenylmethane (TGDDM) or triglycidyl-p-aminophenol; glycidyl ester based epoxy resins.
Amine resin: diaminodiphenylmethane; diaminodiphenyl sulfone; isophorone diamine; naphthalene diamine; aniline novolac; o-ethylaniline novolac; aniline resin obtained by the reaction of aniline with dichloroxylene (xylene chloride); an amine resin obtained by reacting aniline with a substituted biphenyl (e.g., 4 '-bis (chloromethyl) -1,1' -biphenyl and 4,4 '-bis (methoxymethyl) -1,1' -biphenyl) or a substituted benzene (e.g., 1, 4-bis (chloromethyl) benzene, 1, 4-bis (methoxymethyl) benzene and 1, 4-bis (hydroxymethyl) benzene) described in japanese patent No. 6429862.
Active olefin-containing resin: polycondensates of the phenol resins and halogen-based compounds containing an active olefin (e.g., chloromethylstyrene, allyl chloride, methallyl chloride, and acryloyl chloride); polycondensates of phenols containing an active olefin (e.g., 2-allylphenol, 2-propenylphenol, 4-allylphenol, 4-propenylphenol, eugenol (eugenol), and isoeugenol (isoeugenol)) with halogen-based compounds (e.g., 4' -bis (methoxymethyl) -1,1' -biphenyl, 1, 4-bis (chloromethyl) benzene, 4' -difluorobenzophenone, 4' -dichlorobenzophenone, 4' -dibromobenzophenone, and cyanuric chloride); polycondensates of epoxy resins or alcohols with substituted or unsubstituted acrylates (acrylates, methacrylates, 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' -diphenylether bismaleimide, 4' -diphenylsulfone 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-xylylene diisocyanate, m-xylylene diisocyanate, 2, 4-tolylene diisocyanate, 2, 6-tolylene 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 biuret products of isocyanate monomers or isocyanate products obtained by trimerizing the diisocyanate compounds; a polyisocyanate obtained by a urethanization reaction of the isocyanate compound with a polyol compound.
Polyamide resin: aliphatic diamines such as amino acids (6-aminocaproic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, p-aminomethylbenzoic acid, etc.), lactams (e.g.. epsilon. -caprolactam, e.g.. omega. -undecanolactam, e.g.. omega. -lauryllactam) and diamines (ethylene diamine, trimethylene diamine, tetramethylene diamine, pentamethylene diamine, hexamethylene diamine, heptamethylene diamine, octamethylene diamine, nonamethylene diamine, decamethylene diamine, undecane diamine, dodecane diamine, tridecane diamine, tetradecane diamine, pentadecane diamine, hexadecane diamine, heptadecane diamine, octadecane diamine, nonadecane diamine, eicosane diamine, 2-methyl-1, 5-diaminopentane, 2-methyl-1, 8-diaminooctane, cyclohexane diamine, or the like, Alicyclic diamines such as bis- (4-aminocyclohexyl) methane and bis (3-methyl-4-aminocyclohexyl) methane; aromatic diamines such as xylylenediamine) and dicarboxylic acids (aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, and dodecanedioic acid; aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, 2-chloroterephthalic acid, 2-methylterephthalic acid, 5-methylisophthalic acid, 5-sodium sulfoisophthalate, hexahydroterephthalic acid, and hexahydroisophthalic acid; alicyclic dicarboxylic acids such as cyclohexanedicarboxylic acid; dialkyl esters of these dicarboxylic acids and dichlorides) as the main raw material.
Polyimide resin: the diamine is reacted with tetracarboxylic dianhydride (4,4'- (hexafluoroisopropylidene) diphthalic anhydride, 5- (2, 5-dioxotetrahydro-3-furanyl) -3-methyl-cyclohexene-1, 2-dicarboxylic anhydride, pyromellitic dianhydride, 1,2,3, 4-benzenetetracarboxylic dianhydride, 3,3',4,4 '-benzophenonetetracarboxylic dianhydride, 2',3,3 '-benzophenonetetracarboxylic dianhydride, 3,3',4,4 '-biphenyltetracarboxylic dianhydride, 3,3',4,4 '-diphenylsulfonetetracarboxylic dianhydride, 2',3,3 '-biphenyltetracarboxylic dianhydride, methylene-4, 4' -diphthalic dianhydride, 1-ethylene-4, 4 '-Biphthalic dianhydride, 2' -propylene-4, 4 '-Biphthalic dianhydride, 1, 2-ethylene-4, 4' -Biphthalic dianhydride, 1, 3-trimethylene-4, 4 '-Biphthalic dianhydride, 1, 4-tetramethylene-4, 4' -Biphthalic dianhydride, 1, 5-pentamethylene-4, 4 '-Biphthalic dianhydride, 4' -oxydiphthalic dianhydride, thio-4, 4 '-Biphthalic dianhydride, sulfonyl-4, 4' -Biphthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenyl) benzene dianhydride, 1, 3-bis (3, 4-dicarboxyphenoxy) benzene dianhydride, 1, 4-bis (3, 4-dicarboxyphenoxy) benzene dianhydride, 1, 4-bis (3, 4-dicarboxyphenoxy) benzene 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) -1,1,3, 3-tetramethyldisiloxane dianhydride, 2,3,6, 7-naphthalenetetracarboxylic dianhydride, 1,4,5, 8-naphthalenetetracarboxylic dianhydride, 1,2,5, 6-naphthalenetetracarboxylic dianhydride, 3,4,9, 10-perylenetetracarboxylic dianhydride, 2,3,6, 7-anthracenetetracarboxylic dianhydride, 1,2,7, 8-phenanthrenetetracarboxylic dianhydride, vinyltetracarboxylic dianhydride, 1,2,3, 4-butanetetracarboxylic dianhydride, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, cyclopentanetetracarboxylic dianhydride, cyclohexane-1, 2,3, 4-tetracarboxylic dianhydride, cyclohexane-1, 2,4, 5-tetracarboxylic dianhydride, 3,3',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-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 [2,2,2] 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-bis- (3, 4-dicarboxylic anhydride phenyl) ether, 4' -biphenylbis (trimellitic acid monoester anhydride), 9' -bis (3, 4-dicarboxyphenyl) fluorene dianhydride).
Cyanate ester resin: specific examples of the cyanate ester compound obtained by reacting a phenol resin with a cyanogen halide include: dicyanobenzene (dicyanobenzene), tricyclonoxybenzene, dicyanonaphthalene, dicyanobenzene, 2 '-bis (4-cyanatophenyl) propane, bis (4-cyanatophenyl) methane, bis (3, 5-dimethyl-4-cyanatophenyl) methane, 2' -bis (3, 5-dimethyl-4-cyanatophenyl) propane, 2 '-bis (4-cyanatophenyl) ethane, 2' -bis (4-cyanatophenyl) hexafluoropropane, bis (4-cyanatophenyl) sulfone, bis (4-cyanatophenyl) sulfide, phenol novolac cyanate ester, one in which a hydroxyl group of a phenol-dicyclopentadiene co-condensate is converted into a cyanate group, and the like, but is not limited thereto.
In addition, Japanese patent laid-open No. 2005-264154 discloses that a cyanate ester compound obtained by a synthesis method is particularly preferable as a cyanate ester compound because of its low hygroscopicity, excellent 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 octylate, tin octylate, lead acetylacetonate, dibutyltin maleate, or the like, in order to trimerize the cyanate group to form an s-triazine (sym-triazine) ring as necessary. The catalyst is used usually 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 curing agent for a curable resin other than the essential components described in the present invention, such as an epoxy resin. The active ester-based curing agent is preferably a compound having two or more ester groups with high reactivity in one molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxy compounds. The active ester-based hardener is preferably obtained by a condensation reaction between at least one of a carboxylic acid compound and a thiocarboxylic acid compound and at least one of 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 of 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 and the naphthol compound include: hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, phenolphthalein acid (phenolphthalin), 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, benzenetriol, dicyclopentadiene type diphenol compound, phenol novolak, and the like. Here, the "dicyclopentadiene type diphenol compound" refers to a diphenol compound obtained by condensation of two molecules of phenol in one molecule of dicyclopentadiene.
Preferred specific examples of the active ester-based curing agent include active ester compounds having a dicyclopentadiene type diphenol structure, active ester compounds having a naphthalene structure, active ester compounds having an acetyl compound of phenol novolak, and active ester compounds having a benzoyl compound of phenol novolak. Among them, an active ester compound having a naphthalene structure and an active ester compound having a dicyclopentadiene type diphenol structure are more preferable. By "dicyclopentadiene type diphenol structure", it is meant a divalent structural unit comprising phenylene-dicyclopentylene-phenylene.
Examples of commercially available active ester-based curing agents include: "EXB 9451", "EXB 9460S", "HPC-8000-65T", "HPC-8000H-65 TM", "EXB-8000L-65 TM", "EXB-8150-65T" (manufactured by died-son (DIC)) as an active ester compound containing a dicyclopentadiene type diphenol structure; "EXB 9416-70 BK" (manufactured by Dieson (DIC)) as an active ester compound containing a naphthalene structure; "DC 808" (manufactured by mitsubishi chemical corporation) which is an active ester compound containing an acetylated product of phenol novolac; "YLH 1026", "YLH 1030", "YLH 1048" (manufactured by mitsubishi chemical corporation) as an active ester compound including a benzoylate of phenol novolac; "DC 808" (manufactured by mitsubishi chemical corporation) as an active ester-based hardener which is an acetylated phenol novolac; "EXB-9050L-62M" manufactured by Diegon (DIC) as an active ester-based curing agent containing a phosphorus atom.
In the curable resin composition of the present invention, a radical polymerization initiator is preferably used in order to promote self-polymerization of a curable resin capable of radical polymerization such as a maleimide resin or radical polymerization with other components. As the radical polymerization initiator that can be used, there can be mentioned: 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 (tert-butylperoxyisopropyl) benzene; peroxyketals such as t-butyl peroxybenzoate and 1, 1-di-t-butylperoxycyclohexane; alkyl peroxy acid esters such as α -cumyl peroxyneodecanoate, t-butyl peroxypivalate, 1,3, 3-tetramethylbutylperoxy-2-ethylhexanoate, t-amyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-amyl peroxy-3, 5, 5-trimethylhexanoate, t-butyl peroxy-3, 5, 5-trimethylhexanoate, and t-amyl peroxybenzoate; peroxycarbonates such as di-2-ethylhexyl peroxydicarbonate, bis (4-tert-butylcyclohexyl) peroxydicarbonate, tert-butylperoxyisopropyl carbonate, and 1, 6-bis (tert-butylperoxycarbonyloxy) hexane; examples of the conventional radical polymerization initiator include organic peroxides such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroctoate and lauroyl peroxide, azo compounds such as azobisisobutyronitrile, 4 '-azobis (4-cyanovaleric acid) and 2,2' -azobis (2, 4-dimethylvaleronitrile), but the present invention is not limited thereto. Preferred are ketone peroxides, diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, alkyl peroxyesters, peroxycarbonates, and the like, and more preferred are dialkyl peroxides. The amount of the radical polymerization initiator added is preferably 0.01 to 5 parts by mass, and 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.
The curable resin composition of the present invention may be used in combination with a curing accelerator (curing catalyst) as needed. Specific examples of the curing 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, triisopropylmethylammonium salt, trimethyldecylammonium salt, cetyltrimethylammonium salt, and cetyltrimethylammonium hydroxide; quaternary phosphonium salts such as triphenylbenzylphosphonium salt, triphenylethylphosphonium salt and tetrabutylphosphonium salt (the counter ion of the quaternary salt is not particularly limited, and is halogen, organic acid ion, hydroxide ion and the like), transition metal compounds (transition metal salts) such as zinc compounds such as tin octanoate, zinc carboxylate (zinc 2-ethylhexanoate, zinc stearate, zinc behenate and zinc myristate) and zinc phosphate (zinc octylphosphate, zinc stearylphosphate and the like) are particularly preferable. The amount of the curing accelerator to be blended may be 0.01 to 5.0 parts by weight, as required, based on 100 parts by weight of the epoxy resin.
The curable resin composition of the present invention may contain a phosphorus-containing compound as a flame retardancy-imparting component. The phosphorus-containing compound may be a reactive type phosphorus-containing compound or an additive type phosphorus-containing compound. Specific examples of the phosphorus-containing compound include: phosphoric acid esters such as trimethyl phosphate, triethyl phosphate, tricresyl phosphate, trixylyl phosphate, tolyldiphenyl phosphate, tolyl-2, 6-dixylyl phosphate, 1, 3-phenylenebis (dixylyl phosphate), 1, 4-phenylenebis (dixylyl phosphate), and 4,4' -biphenyl (dixylyl phosphate); phosphane (phosphane) compounds such as 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide and 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide; phosphorus-containing epoxy compounds, red phosphorus, and the like obtained by reacting an epoxy resin with active hydrogen of the aforementioned phosphine group are preferably phosphoric esters, phospholanes, or phosphorus-containing epoxy compounds, and particularly preferably 1, 3-phenylene bis (dixylyl) phosphate, 1, 4-phenylene bis (dixylyl) phosphate), 4' -biphenyl (dixylyl) phosphate, or phosphorus-containing epoxy compounds. The content of the phosphorus-containing compound is preferably in the range of (phosphorus-containing compound)/(total epoxy resin) from 0.1 to 0.6 (weight ratio). If the amount is 0.1 or less, the flame retardancy is insufficient, and if the amount is 0.6 or more, the moisture absorption and dielectric properties of the cured product may be adversely affected.
Further, an antioxidant may be added to the curable resin composition of the present invention as needed. Examples of the antioxidant that can be used include phenol-based, sulfur-based, and phosphorus-based antioxidants. The antioxidants may be used alone or in combination of two or more. The amount of the antioxidant used is usually 0.008 parts by weight to 1 part by weight, preferably 0.01 parts by weight to 0.5 parts 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 phenol-based antioxidant 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, and 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 ' -hexamethylenebis (3, 5-di-tert-butyl-4-hydroxy-hydrocinnamide), Bisphenols such as 2, 2-thio-diethylene bis [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, and calcium bis (3, 5-di-tert-butyl-4-hydroxybenzyl sulfonate); 1,1, 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 glycol bis [3,3' -bis- (4' -hydroxy-3 ' -tert-butylphenyl) butyrate, tris- (3, 5-di-tert-butyl-4-hydroxybenzyl) -isocyanurate, 1,3, 5-tris (3',5' -di-tert-butyl-4 ' -hydroxybenzyl) -s-triazine-2, 4,6- (1H,3H,5H) trione, tocopherol, and the like.
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-based antioxidant include: phosphites such as triphenyl phosphite, diphenylisodecyl phosphite, phenyldiisodecyl phosphite, tris (nonylphenyl) phosphite, pentaerythritol diisodecyl phosphite, tris (2, 4-di-tert-butylphenyl) phosphite, cycloneopentanetetraylbis (octadecyl) phosphite, cycloneopentanetetraylbis (2, 4-di-tert-butylphenyl) phosphite, cycloneopentanetetraylbis (2, 4-di-tert-butyl-4-methylphenyl) phosphite, and bis [ 2-tert-butyl-6-methyl-4- {2- (octadecyloxycarbonyl) ethyl } phenyl ] halophosphite; 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, and 10-decyloxy-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.
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 (HALS) or the like. The HALS are not particularly limited, and representative HALS include: dibutylamine-condensation product of 1,3, 5-triazin-N, N' -bis (2,2,6, 6-tetramethyl-4-piperidyl) -1, 6-hexamethylenediamine and N- (2,2,6, 6-tetramethyl-4-piperidyl) butylamine, dimethyl succinate-1- (2-hydroxyethyl) -4-hydroxy-2, 2,6, 6-tetramethylpiperidine condensation product, poly [ (6- (1,1,3, 3-tetramethylbutyl) amino-1, 3, 5-triazine-2, 4-diyl } { (2,2,6, 6-tetramethyl-4-piperidyl) imino } hexamethylene { (2,2,6, 6-tetramethyl-4-piperidyl) imino } ], and a salt thereof, Bis (1,2,2,6, 6-pentamethyl-4-piperidyl) [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] butyl malonate, bis (2,2,6, 6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6, 6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6, 6-di-t-butyl-4-hydroxybenzyl) -2-n-butylmalonate, and the like. The HALS may be used alone or in combination of two or more.
Further, a binder resin may be blended as necessary in the curable resin composition of the present invention. Examples of the binder resin include, but are not limited to, butyral resin, acetal resin, acrylic resin, epoxy-nylon resin, Nitrile Butadiene Rubber (NBR) -phenol resin, epoxy-NBR resin, polyamide resin, polyimide resin, and silicone resin. The amount of the binder resin to be blended is preferably within a range not impairing 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, as required, based on 100 parts by mass of the resin component.
Further, in the curable resin composition of the present invention, if necessary, a powder 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 (steatite), spinel (spinel), mullite (mullite), titanium dioxide, talc (talc), clay, iron oxide, asbestos (asbestos), glass powder, or an inorganic filler obtained by forming these into a spherical or crushed shape may be added. In particular, when a curable resin composition for semiconductor encapsulation is obtained, 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%.
The curable resin composition of the present invention may contain conventional additives as needed. Specific examples of the additives that can be used include polybutadiene and modified products thereof, modified products of acrylonitrile copolymers, surface treatment agents for fillers such as polyphenylene ether, polystyrene, polyethylene, polyimide, fluorine resins, silicone gel, silicone oil, and silane coupling agents, and colorants such as mold release agents, carbon black, phthalocyanine blue, and phthalocyanine green. The amount of these additives is preferably 1,000 parts by mass or less, and 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 components at 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 carried out to obtain the cured product of the present invention. Alternatively, 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 to cure the composition.
The curable resin composition of the present invention obtained in this 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 resin composition is useful as an insulating material, a laminate (such as a printed wiring board, a Ball Grid Array (BGA) substrate, and a build-up substrate), a sealing material, and a resist. In addition, the resin composition can be used in the fields of coating materials, adhesives, and the like, in addition to molding materials and composite materials. Solder reflow resistance is particularly beneficial in semiconductor sealing.
A semiconductor device is sealed with the curable resin composition of the present invention. Examples of the semiconductor device include: dual in-line package (DIP), Quad Flat Package (QFP), Ball Grid Array (BGA), Chip Size Package (CSP), Small Outline Package (SOP), Thin Small Outline Package (TSOP), 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 respective components may be mixed uniformly or may be prepolymerized. For example, the curable resin of the present invention is heated in the presence or absence of a catalyst or in the presence or absence of a solvent to thereby carry out prepolymerization. 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, or an acid anhydride compound, and other additives may be added to the curable resin to perform prepolymerization. For the mixing or prepolymerization of the respective components, for example, an extruder, kneader, roll or the like is used in the absence of a solvent, and a reaction vessel with a stirring device or the like is used in the presence of a solvent.
As a method of uniformly mixing, mixing is performed at a temperature in the range of 50 to 100 ℃ by fusing using a device such as a kneader, a roller, a planetary mixer, or the like, to prepare a uniform resin composition. The obtained resin composition may be pulverized and then molded into a cylindrical ingot by a molding machine such as a tablet machine, or into a granulated powder or powder, or these compositions 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 article. The obtained molded article is a non-tacky molded article at 0 to 20 ℃ and hardly suffers from deterioration in fluidity and curability even when stored at-25 to 0 ℃ for 1 week or more.
The molded article thus obtained can be molded into a cured product by a transfer molding machine or a compression molding machine.
The curable resin composition of the present invention may be prepared by adding an organic solvent to a varnish-like composition (hereinafter referred to as a varnish). The curable resin composition of the present invention can be prepared into a cured product 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, if necessary, to prepare a varnish, impregnating the varnish into a base material such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, alumina fiber, or paper, drying the impregnated base material by heating, and hot-press molding the obtained 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, in the mixture of the curable resin composition of the present invention and the solvent. In addition, in the case of a liquid composition, a curable resin cured product containing carbon fibers can also be obtained directly by, for example, Resin Transfer Molding (RTM).
The curable composition of the present invention can also be used as a modifier for a film-type composition. Specifically, it can be used in the case of improving the flexibility of the B-stage. Such a film-type resin composition is obtained as a sheet-like adhesive by coating a curable resin composition varnish of the present invention on a release film, removing the solvent under heating, and then performing 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 melted by heating and reduced in viscosity to impregnate reinforcing fibers such as glass fibers, carbon fibers, polyester fibers, polyamide fibers, and alumina fibers with the composition, 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, polyparaphenyleneterephtalamide (kevlar (registered trademark)), wholly aromatic polyamides, and polyesters; and organic fibers such as polyparaphenylene benzoxazole (polyparaphenylene benzoxazole), polyimide, and carbon fibers, but are not particularly limited thereto. The shape of the substrate is not particularly limited, and examples thereof include woven fabric, nonwoven fabric, roving (roving), and chopped strand mat (chopped strand mat). As weaving methods of woven fabrics, plain weave, basket weave (basket weave), twill weave (twill weave), and the like are known, and these weaving methods can be used by being appropriately selected according to the intended use and performance. It is preferable to use a glass woven fabric subjected to a fiber-opening treatment or a surface treatment with a silane coupling agent or the like. The thickness of the substrate is not particularly limited, but is preferably about 0.01mm to 0.4 mm. Alternatively, the varnish may be impregnated into reinforcing fibers and then heated and dried to obtain a prepreg.
The laminate of the present embodiment includes one or more sheets of the prepreg. The laminate is not particularly limited as long as it is a laminate including one or more prepregs, and may have any other layer. The method for producing the laminate is not particularly limited, and any conventional method can be suitably used. For example, in the case of forming a metal foil-clad laminate, a multistage press, a multistage vacuum press, a continuous forming machine, an autoclave forming machine, or the like can be used, and the laminate can be obtained by laminating the prepregs and performing heat-pressure forming. In this case, the heating temperature is not particularly limited, but is preferably 65 to 300 ℃, and more preferably 120 to 270 ℃. The pressure for pressing is not particularly limited, but when the pressure is too high, it is difficult to adjust the solid content of the resin in the laminate and the quality is not stable, and when the pressure is too low, bubbles or the adhesion between the laminates is deteriorated, and therefore, it is preferably 2.0 to 5.0MPa, and more preferably 2.5 to 4.0 MPa. The laminate of the present embodiment can be preferably used as a metal foil-clad laminate described later by including a layer having a metal foil.
The prepreg is cut into a desired shape, and is laminated with a copper foil or the like as necessary, and then the laminate is heated and cured by applying pressure to the curable resin composition by a press molding method, an autoclave molding method, a sheet winding (sheet winding) molding method or the like, whereby a laminate (printed wiring board) for electric and electronic use or a carbon fiber reinforced material can be obtained.
The cured product of the present invention can be used for various applications such as molding materials, adhesives, composite materials, and coatings. The cured product of the curable resin composition of the present invention exhibits excellent heat resistance and dielectric properties, and therefore can be suitably used for an encapsulating material for a semiconductor element, an encapsulating material for a liquid crystal display element, an encapsulating material for an organic Electroluminescence (EL) element, an electric and electronic component such as a printed wiring board and a build-up laminate, or a composite material for a lightweight high-strength structural material such as a carbon fiber-reinforced plastic or a glass fiber-reinforced plastic.
Examples
Next, the present invention will be described more specifically by examples. Hereinafter, unless otherwise specified, parts are parts by weight. The present invention is not limited to these examples.
Various analysis methods used in examples are described below.
< amine equivalent >
The amine equivalent was determined as the value obtained in accordance with Japanese Industrial Standards (JIS) K-7236, annex A (method for modifying glycidylamine).
< softening point >
Measured according to JIS K-7234.
< ICI viscosity (150 ℃ C.) >
Measured according to JIS K-7117-2.
< weight average molecular weight (Mw) >)
The calculation was performed by polystyrene conversion using a polystyrene standard solution.
Gel Permeation Chromatograph (GPC): DGU-20A3R, LC-20AD, SIL-20AHT, RID-20A, SPD-20A, CTO-20A, CBM-20A (all manufactured by Shimadzu corporation)
Pipe column: soidex KF-603, KF-602X 2, KF-601X 2
Connecting eluent: tetrahydrofuran (THF)
Flow rate: 0.5ml/min.
Temperature of the pipe column: 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 azeotropic distillation trap and a stirrer was charged with 198 parts of xylene formaldehyde resin (Nikanol (NIKANOL) G, manufactured by Fudao (Fudow) Co., Ltd.), 622 parts of 2-ethyl-6-methylaniline (manufactured by Tokyo chemical Co., Ltd.), 300 parts of toluene and 82 parts of activated clay (manufactured by Nippon activated clay Co., Ltd.), reacted at 120 ℃ for 1 hour, and then heated to 150 ℃ while extracting the distillate, and the temperature was maintained for 4 hours. Thereafter, the temperature was raised to 200 ℃ and the reaction was carried out at 200 ℃ for 10 hours. After cooling, the reaction mixture was diluted with 300 parts of toluene, and the activated clay was removed by filtration, and then the solvent and the excess 2-ethyl-6-methylaniline were distilled off under heating and reduced pressure to obtain 315 parts of an aromatic amine resin (A1) (softening point: 65 ℃, melt viscosity: 0.13 pas, amine equivalent: 199g/eq, Mw: 581). The 1H-N m R chart of the obtained amine resin is shown in fig. 1.
1H-NMR (400MHz, dimethyl sulfoxide (DMSO) -d 6): δ (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]
A flask equipped with a thermometer, a cooling tube, a dean stark azeotropic distillation trap, and a stirrer was charged with 221 parts of maleic anhydride (manufactured by tokyo chemical corporation) and 100 parts of toluene, water and toluene azeotropic by heating were cooled and separated, and 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 maintaining the system at 80 to 85 ℃. After 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, the azeotropic condensation water and toluene were cooled and separated under reflux, and only toluene as an organic layer was returned to the system to be dehydrated, and the reaction was carried out for 20 hours. After the reaction was completed, 600 parts of toluene was added, and p-toluenesulfonic acid and excess maleic anhydride were removed by repeated water washing, and water was removed from the system by azeotropic distillation by heating. Then, the reaction solution was concentrated to obtain a resin solution containing 70% by weight of maleimide resin (M1). The weight average molecular weight (Mw) of the maleimide resin (M1) was 827. FIG. 2 shows a graph of 1H-N M R of the case (M1') in which the maleimide resin (M1) was extracted as a solid by concentration under reduced pressure.
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 (NIKANOL) G, manufactured by Fudao (Fudow) Co., Ltd.), 738 parts of aniline (manufactured by Tokyo chemical Co., Ltd.), 100 parts of toluene, and 95 parts of activated clay, reacted at 120 ℃ for 1 hour, and then heated to 150 ℃ while extracting a distillate, and held for 4 hours. Thereafter, the temperature was raised to 200 ℃ and the reaction was carried out at 200 ℃ for 10 hours. After cooling, the reaction mixture was diluted with 300 parts of toluene, and the activated clay (manufactured by activated clay corporation) was removed by filtration, and then the solvent and the excess aniline were distilled off under heating and reduced pressure, thereby obtaining 314 parts of an aromatic amine resin (A2) (softening point: 66.6 ℃, melt viscosity: 0.23 pas, amine equivalent: 198g/eq, Mw: 734).
Comparative example 2
A flask equipped with a thermometer, a cooling tube, a dean stark azeotropic distillation trap, and a stirrer was charged with 186 parts of maleic anhydride (manufactured by tokyo chemical corporation) and 250 parts of toluene, water and toluene azeotropic by heating were cooled and separated, and only toluene as an organic layer was returned to the system to be dehydrated. Then, 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 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 corporation) was added, the azeotropic condensation water and toluene were cooled and separated under reflux, and 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 water washing was performed, and as a result, the mixture was separated into three layers during liquid separation and was not extracted.
Comparative example 3
The same reaction as in comparative example 2 was carried out, and after completion of the reaction, 3000 parts of toluene and 300 parts of N-methyl-2-pyrrolidone were added, and washing with water was repeated to remove p-toluenesulfonic acid and excess maleic anhydride, and water was removed from the system by azeotropic distillation with heating. Then, the reaction solution was concentrated to obtain a resin solution containing 70% by weight of maleimide resin (M2). The maleimide resin (M2) had a weight average molecular weight (Mw) of 1204.
It was confirmed that the weight average molecular weight of the aromatic amine resin (a1) obtained in example 1 was small and the molecular weight distribution was sharp, as compared with the aromatic amine resin (a2) obtained in comparative example 2. Since the weight average molecular weight of the aromatic amine resin (a2) exceeded 700, the maleimide resin (M2) obtained from the aromatic amine resin (a2) was difficult to purify by ordinary water washing as shown in comparative example 2 due to the high and low molecular weight and polarity, and impurities such as acid catalysts could not be removed. The maleimide resin (M2) was not washed with water unless a highly polar high boiling point solvent was used in combination with a large amount of an organic solvent as shown in comparative example 3. Therefore, the aromatic amine resin (a1) is excellent in terms of reduction of industrial waste, improvement of the yield in the same facility, simplification of the production process, and the like, because of the problem of the high-boiling point solvent remaining in the maleimide resin.
Example 3 and comparative examples 4 and 5
The maleimide compound (M1) obtained in example 2, which was extracted as a solid by concentration under reduced pressure (M1'), BMI-2300: aniline novolak type maleimide compounds (manufactured by Daihu chemical industries, Ltd.), biphenyl aralkyl type epoxy resins (NC-3000-L, manufactured by Nippon chemical Co., Ltd.), biphenyl aralkyl type phenol resins (Kayahard (KAYAHARD) GPH-65, manufactured by Nippon chemical Co., Ltd.), 2E-4MZ (2-ethyl-4-methylimidazole, manufactured by Sichuan chemical Co., Ltd.) as a curing accelerator were melted and mixed in a metal container, poured directly into a mold, and cured at 220 ℃ for 2 hours.
[ example 4]
The maleimide compound (M1) (M1') obtained in example 2 and dicumyl peroxide (Kayaku Akzo, chemical) were mixed at the ratio (parts by mass) shown in table 1, and the mixture was taken out as a solid by concentration under reduced pressure, heated and melted in a metal container, poured into a mold, and cured at 220 ℃ for 2 hours.
The results of measuring the following items for 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 δ is the maximum value, as measured by a dynamic viscoelastometer.
Dynamic viscoelasticity measuring apparatus: DMA-2980 manufactured by TA instruments (TA-instruments)
Temperature rise rate: 2 ℃ per minute
< 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 carried out with sample sizes of 1.7mm in width by 100mm in length and 1.7mm in thickness.
[ Table 1]
M1': the maleimide resin was extracted as a solid by distilling off the solvent under reduced pressure and heating as described in example 2
BMI-2300: aniline Novolac type maleimide compound (manufactured by Daghe chemical industries Co., Ltd.)
DCP: dicumyl peroxide (chemical drug manufactured by Aksu Co., Ltd.)
NC-3000-L: biphenylalkyl epoxy resin (manufactured by Nippon chemical Co., Ltd.)
GPH-65: biphenylalkyl phenol resin (manufactured by Nippon chemical Co., Ltd.)
2E-4 MZ: 2-Ethyl-4-methylimidazole (manufactured by Siguocho chemical Co., Ltd.)
As is clear from table 1, examples 3 and 4 have high heat resistance and excellent dielectric characteristics.
Industrial applicability
The curable resin composition of the present invention is useful for various composite materials including insulating materials for electric and electronic parts (highly reliable semiconductor sealing materials, etc.), laminated boards (printed wiring boards, BGA substrates, build-up substrates, etc.), adhesives (conductive adhesives, etc.) and Carbon Fiber Reinforced Plastics (CFRP), and coatings.
Claims (9)
2. The aromatic amine resin according to claim 1, which is obtained by reacting an aniline compound substituted at the 2, 6-position with an alkylbenzaldehyde resin.
4. The aromatic amine resin of claim 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 claims 1 to 4, having a softening point of 80 ℃ or lower.
6. The aromatic amine resin according to any one of claims 1 to 5, having a weight average molecular weight of 300 to 700.
7. A maleimide resin obtained by reacting the aromatic amine resin of any one of claims 1 to 6 with maleic acid or maleic anhydride.
8. A curable resin composition comprising the maleimide resin according to claim 7.
9. A cured product obtained by curing the curable resin composition according to claim 8.
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JP2024004392A (en) | 2022-06-28 | 2024-01-16 | Dic株式会社 | Polymaleimide resin, curable composition, cured product, prepreg, circuit board, build-up film, semiconductor sealing material and semiconductor device |
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JP5019585B2 (en) * | 2007-02-26 | 2012-09-05 | 日本化薬株式会社 | Epoxy resin composition, cured product thereof, and fiber-reinforced composite material |
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WO2016117584A1 (en) * | 2015-01-21 | 2016-07-28 | 日本化薬株式会社 | Aromatic amine resin, and epoxy resin composition and cured product thereof |
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JPH03190914A (en) * | 1989-12-19 | 1991-08-20 | Mitsui Toatsu Chem Inc | Production of aromatic amine resin |
CN108884212A (en) * | 2016-03-29 | 2018-11-23 | 日本化药株式会社 | Maleimide resin, hardening resin composition and its hardening thing |
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KR20220004616A (en) | 2022-01-11 |
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