JP6836622B2 - 芳香族アミン樹脂、マレイミド樹脂、硬化性樹脂組成物およびその硬化物 - Google Patents
芳香族アミン樹脂、マレイミド樹脂、硬化性樹脂組成物およびその硬化物 Download PDFInfo
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- JP6836622B2 JP6836622B2 JP2019078504A JP2019078504A JP6836622B2 JP 6836622 B2 JP6836622 B2 JP 6836622B2 JP 2019078504 A JP2019078504 A JP 2019078504A JP 2019078504 A JP2019078504 A JP 2019078504A JP 6836622 B2 JP6836622 B2 JP 6836622B2
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- Prior art keywords
- resin
- aromatic amine
- acid
- maleimide
- bis
- Prior art date
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- 229920005989 resin Polymers 0.000 title claims description 143
- 239000011347 resin Substances 0.000 title claims description 143
- 150000004982 aromatic amines Chemical class 0.000 title claims description 44
- 239000011342 resin composition Substances 0.000 title claims description 44
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title claims description 33
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 35
- 150000001875 compounds Chemical group 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- 239000008096 xylene Substances 0.000 claims description 8
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 7
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- -1 2-ethyl- Chemical group 0.000 description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 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 32
- 238000006243 chemical reaction Methods 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 239000003822 epoxy resin Substances 0.000 description 16
- 229920000647 polyepoxide Polymers 0.000 description 16
- 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
- 239000000203 mixture Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 239000005011 phenolic resin Substances 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000004927 clay Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229920003986 novolac Polymers 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- 239000011973 solid acid Substances 0.000 description 8
- 229920000049 Carbon (fiber) Polymers 0.000 description 7
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000004917 carbon fiber Substances 0.000 description 7
- 239000004643 cyanate ester Substances 0.000 description 7
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 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
- 230000003078 antioxidant effect Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 150000004678 hydrides Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 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 4
- 238000005160 1H NMR spectroscopy Methods 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
- 239000003377 acid catalyst Substances 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012948 isocyanate Substances 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
- 239000007788 liquid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 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
- 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 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
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000008393 encapsulating agent Substances 0.000 description 3
- 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
- 239000004611 light stabiliser Substances 0.000 description 3
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 2
- DAJPMKAQEUGECW-UHFFFAOYSA-N 1,4-bis(methoxymethyl)benzene Chemical compound COCC1=CC=C(COC)C=C1 DAJPMKAQEUGECW-UHFFFAOYSA-N 0.000 description 2
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 2
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- 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
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 230000007704 transition Effects 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
- SUXIKHBBPQWLHO-UHFFFAOYSA-N trihydroxy-(8-methylnonyl)-(8-methyl-1-phenylnonyl)-lambda5-phosphane Chemical compound CC(C)CCCCCCCP(O)(O)(O)C(CCCCCCC(C)C)C1=CC=CC=C1 SUXIKHBBPQWLHO-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
- 238000009941 weaving Methods 0.000 description 1
- 238000004804 winding Methods 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
- JRHDFVNUWLMGBU-UHFFFAOYSA-L zinc octyl phosphate Chemical compound C(CCCCCCC)OP(=O)([O-])[O-].[Zn+2] JRHDFVNUWLMGBU-UHFFFAOYSA-L 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
- 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
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
Description
[1]
下記式(1)で表される芳香族アミン樹脂。
[2]
2,6−位に置換されたアニリン系化合物とアルキルベンゼンホルマリン樹脂とを反応させて得られる前項[1]に記載の芳香族アミン樹脂。
[3]
下記式(2)で表される前項[1]または[2]に記載の芳香族アミン樹脂。
[4]
2−エチル−6−メチルアニリンとキシレンホルマリン樹脂とを反応させて得られる前項[3]に記載の芳香族アミン樹脂。
[5]
軟化点が80℃以下である前項[1]乃至[4]のいずれか一項に記載の芳香族アミン樹脂。
[6]
重量平均分子量が300〜700である前項[1]乃至[5]のいずれか一項に記載の芳香族アミン樹脂。
[7]
前項[1]乃至[8]のいずれか一項に記載の芳香族アミン樹脂と、マレイン酸またはマレイン酸無水物とを反応させることにより得られるマレイミド樹脂。
[8]
前項[7]に記載のマレイミド樹脂を含有する硬化性樹脂組成物。
[9]
前項[8]に記載の硬化性樹脂組成物を硬化して得られる硬化物。
また、本発明の芳香族アミン樹脂から誘導されるマレイミド樹脂を含有する硬化性樹脂組成物の硬化物は、高耐熱性、低誘電特性に優れた特性を有するものであり、電気電子部品の封止や回路基板、炭素繊維複合材などに有用である。
本発明の芳香族アミンの重量平均分子量は300〜700であることが好ましく、更に好ましくは、400〜600である。分子量分布は、GPC(ゲル浸透クロマトグラフィー)により測定することができる。重量平均分子量が700を超えるアミン樹脂を原料とし、マレイミド樹脂を合成した場合、その分子量の大きさ、および極性の高さから、水洗による精製が困難となり、酸触媒等の不純物を取り除くことが困難となる。重量平均分子量が300未満であるとワニスとした際の溶剤安定性が低下する可能性がある。
上記硬化性樹脂の使用量は、本発明のマレイミド樹脂に対して、通常10質量倍未満、好ましくは3質量倍未満、さらに好ましくは2質量倍未満、特に好ましくは1.5質量部未満の質量範囲である。10質量倍以上の場合、本発明のマレイミド樹脂の濃度が低くなり、十分な耐熱性や誘電特性が得られなくなる可能性がある。また、好ましい下限値は0.2質量倍以上、さらに好ましくは0.5質量倍以上である。
また、特開2005−264154号公報に合成方法が記載されているシアネートエステル化合物は、低吸湿性、難燃性、誘電特性に優れているためシアネートエステル化合物として特に好ましい。
シアネート樹脂は、必要に応じてシアネート基を三量化させてsym−トリアジン環を形成するために、ナフテン酸亜鉛、ナフテン酸コバルト、ナフテン酸銅、ナフテン酸鉛、オクチル酸亜鉛、オクチル酸錫、鉛アセチルアセトナート、ジブチル錫マレエート等の触媒を含有させることもできる。触媒は、熱硬化性樹脂組成物の合計質量100質量部に対して通常0.0001〜0.10質量部、好ましくは0.00015〜0.0015質量部使用する。
カルボン酸化合物としては、例えば、安息香酸、酢酸、コハク酸、マレイン酸、イタコン酸、フタル酸、イソフタル酸、テレフタル酸、ピロメリット酸等が挙げられる。
フェノール化合物又はナフトール化合物としては、例えば、ハイドロキノン、レゾルシン、ビスフェノールA、ビスフェノールF、ビスフェノールS、フェノールフタリン、メチル化ビスフェノールA、メチル化ビスフェノールF、メチル化ビスフェノールS、フェノール、o−クレゾール、m−クレゾール、p−クレゾール、カテコール、α−ナフトール、β−ナフトール、1,5−ジヒドロキシナフタレン、1,6−ジヒドロキシナフタレン、2,6−ジヒドロキシナフタレン、ジヒドロキシベンゾフェノン、トリヒドロキシベンゾフェノン、テトラヒドロキシベンゾフェノン、フロログルシン、ベンゼントリオール、ジシクロペンタジエン型ジフェノール化合物、フェノールノボラック等が挙げられる。ここで、「ジシクロペンタジエン型ジフェノール化合物」とは、ジシクロペンタジエン1分子にフェノール2分子が縮合して得られるジフェノール化合物をいう。
活性エステル系硬化剤の好ましい具体例としては、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物、ナフタレン構造を含む活性エステル化合物、フェノールノボラックのアセチル化物を含む活性エステル化合物、フェノールノボラックのベンゾイル化物を含む活性エステル化合物が挙げられる。中でも、ナフタレン構造を含む活性エステル化合物、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物がより好ましい。「ジシクロペンタジエン型ジフェノール構造」とは、フェニレン− ジシクロペンチレン−フェニレンからなる2価の構造単位を表す。
活性エステル系硬化剤の市販品としては、例えば、ジシクロペンタジエン型ジフェノール構造を含む活性エステル化合物として、「EXB9451」、「EXB9460」、「EXB9460S」、「HPC−8000−65T」、「HPC−8000H−65TM」、「EXB−8000L−65TM」、「EXB−8150−65T」(DIC社製);ナフタレン構造を含む活性エステル化合物として「EXB9416−70BK」(DIC社製);フェノールノボラックのアセチル化物を含む活性エステル化合物として「DC808」(三菱化学社製);フェノールノボラックのベンゾイル化物を含む活性エステル化合物として「YLH1026」、「YLH1030」、「YLH1048」(三菱化学社製);フェノールノボラックのアセチル化物である活性エステル系硬化剤として「DC808」(三菱化学社製);リン原子含有活性エステル系硬化剤としてDIC社製の「EXB−9050L−62M」;等が挙げられる。
得られた成型体についてトランスファー成型機、コンプレッション成型機にて硬化物に成型することができる。
上記プリプレグを所望の形に裁断、必要により銅箔などと積層後、積層物にプレス成形法やオートクレーブ成形法、シートワインディング成形法などで圧力をかけながら硬化性樹脂組成物を加熱硬化させることにより電気電子用積層板(プリント配線板)や、炭素繊維強化材を得ることができる。
以下に実施例で用いた各種分析方法について記載する。
<アミン当量>
JIS K−7236 付属書A(グリシジルアミンの補正法)に準拠し、得られた値をアミン当量とした。
<軟化点>
JIS K−7234に準拠して測定。
<ICI粘度(150℃)>
JIS K−7117−2に準拠して測定。
<重量平均分子量(Mw)>
ポリスチレン標準液を用いてポリスチレン換算により算出した。
GPC:DGU−20A3R,LC−20AD,SIL−20AHT,RID−20A,SPD−20A,CTO−20A,CBM−20A(いずれも島津製作所製)
カラム:Shodex KF−603、KF−602x2、KF−601x2)
連結溶離液:テトラヒドロフラン
流速:0.5ml/min.
カラム温度:40℃
検出:RI(示差屈折検出器)
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコにキシレンホルマリン樹脂(ニカノールG フドー株式会社製)198部、2−エチル−6−メチルアニリン(東京化成社製)622部とトルエン300部、活性白土(日本活性白土社製)82部を仕込み、120℃で1時間反応後、留出物を抜き出しながら150℃まで昇温し、4時間保持した。その後、200℃まで昇温し、200℃で10時間反応を行った。放冷後、トルエン300部で希釈し、濾過で活性白土を除去後、加熱減圧下において溶剤および過剰の2−エチル−6−メチルアニリンを留去することにより芳香族アミン樹脂(A1)315部を得た(軟化点:65℃、溶融粘度は0.13Pa・s、アミン当量:199g/eq、Mw:581)。得られたアミン樹脂の1H−NМRチャートを図1に示す。
1H−NMR(400MHz,DMSO−d6);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)
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコに無水マレイン酸(東京化成社製)221部とトルエン100部を仕込み、加熱して共沸してくる水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行った。次に、実施例1で得られた芳香族アミン樹脂(A1)300部をN−メチル−2−ピロリドン50部とトルエン150部の混合溶剤に溶解した樹脂溶液を、系内を80〜85℃に保ちながら1時間かけて滴下した。滴下終了後、同温度で2時間反応を行い、p−トルエンスルホン酸6部を加えて、還流条件で共沸してくる縮合水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行いながら20時間反応を行った。反応終了後、トルエン600部を追加し、水洗を繰り返してp−トルエンスルホン酸及び過剰の無水マレイン酸を除去し、加熱して共沸により水を系内から除いた。次いで反応溶液を濃縮して、マレイミド樹脂(M1)を70%含有する樹脂溶液を得た。マレイミド樹脂(M1)の重量平均分子量(Mw)は827であった。マレイミド樹脂(M1)を減圧濃縮により固形取り出ししたもの(M1’)の1H−NМRチャートを図2に示す。
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)
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコにキシレンホルマリン樹脂(ニカノールG フドー株式会社製)210部、アニリン(東京化成社製)738部とトルエン100部、活性白土95部を仕込み、120℃で1時間反応後、留出物を抜き出しながら150℃まで昇温し、4時間保持した。その後、200℃まで昇温し、200℃で10時間反応を行った。放冷後、トルエン300部で希釈し、濾過で活性白土(日本活性白土社製)を除去後、加熱減圧下において溶剤および過剰のアニリンを留去することにより芳香族アミン樹脂(A2)314部を得た(軟化点:66.6℃、溶融粘度は0.23Pa・s、アミン当量:198g/eq、Mw:734)。
温度計、冷却管、ディーンスターク共沸蒸留トラップ、撹拌機を取り付けたフラスコに無水マレイン酸(東京化成社製)186部とトルエン250部を仕込み、加熱して共沸してくる水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行った。次に、比較例1で得られた芳香族アミン樹脂(A2)250部をN−メチル−2−ピロリドン250部とトルエン250部の混合溶剤に溶解した樹脂溶液を、系内を80〜85℃に保ちながら1時間かけて滴下した。滴下終了後、同温度で2時間反応を行い、p−トルエンスルホン酸(東京化成社製)5部を加えて、還流条件で共沸してくる縮合水とトルエンを冷却・分液した後、有機層であるトルエンだけを系内に戻して脱水を行いながら20時間反応を行った。反応終了後、トルエン500部追加し、水洗を実施したところ、分液時に3層に分離してしまい、抽出できなかった。
[比較例3]
比較例2と同様の反応を行い、反応終了後、トルエン3000部、N−メチル−2−ピロリドン300部を追加し、水洗を繰り返してp−トルエンスルホン酸及び過剰の無水マレイン酸を除去し、加熱して共沸により水を系内から除いた。次いで反応溶液を濃縮して、マレイミド樹脂(M2)を70重量%含有する樹脂溶液を得た。マレイミド樹脂(M2)の重量平均分子量(Mw)は1204であった。
実施例2で得られたマレイミド化合物(M1)を減圧濃縮により固形取り出ししたもの(M1’)、MIR−2300:アニリンノボラック型マレイミド化合物(大和化成工業社製)、ビフェニルアラルキル型エポキシ樹脂(NC−3000−L 日本化薬株式会社製)、ビフェニルアラルキル型フェノール樹脂(KAYAHARD GPH−65 日本化薬株式会社製)、硬化促進剤として2E4MZ(2−エチル−4−メチルイミダゾール 四国化成社製)を表1の割合(質量部)で配合し、金属容器中で加熱溶融混合してそのまま金型に流し込み、220℃で2時間硬化させた。
実施例2で得られたマレイミド化合物(M1)を減圧濃縮により固形取り出ししたもの(M1’)およびジクミルパーオキサイド(化薬アクゾ社製)を表1の割合(質量部)で配合し、金属容器中で加熱溶融混合してそのまま金型に流し込み、220℃で2時間硬化させた。
このようにして得られた硬化物の物性を下記項目について測定した結果を表1に示す。
・ガラス転移温度:動的粘弾性試験機により測定し、tanδが最大値のときの温度。
動的粘弾性測定器:TA−instruments製DMA−2980
昇温速度:2℃/分
<誘電率試験・誘電正接試験>
・(株)関東電子応用開発製の1GHz空洞共振器を用いて、空洞共振器摂動法にてテストを行った。ただし、サンプルサイズは幅1.7mm×長さ100mmとし、厚さは1.7mmで試験を行った。
MIR−2300:アニリンノボラック型マレイミド化合物(大和化成工業社製)
DCP:ジクミルパーオキサイド(化薬アクゾ社製)
NC−3000−L:ビフェニルアラルキル型エポキシ樹脂(日本化薬社製)
GPH−65:ビフェニルアラルキル型フェノール樹脂(日本化薬社製)
2E−4MZ:2−メチル−4−イミダゾール(四国化成社製)
Claims (8)
- 下記式(1)で表される芳香族アミン樹脂と、マレイン酸またはマレイン酸無水物とを反応させることにより得られるマレイミド樹脂。
- 前記式(1)で表される芳香族アミン樹脂が、2,6−位に置換されたアニリン系化合物とアルキルベンゼンホルマリン樹脂とを反応させて得られる芳香族アミン樹脂である請求項1に記載のマレイミド樹脂。
- 下記式(2)で表される芳香族アミン樹脂と、マレイン酸またはマレイン酸無水物とを反応させることにより得られるマレイミド樹脂。
- 前記式(2)で表される芳香族アミン樹脂が、2−エチル−6−メチルアニリンとキシレンホルマリン樹脂とを反応させて得られる芳香族アミン樹脂である請求項3に記載のマレイミド樹脂。
- 前記式(1)で表される芳香族アミン樹脂または前記式(2)で表される芳香族アミン樹脂の軟化点が80℃以下である請求項1乃至4のいずれか一項に記載のマレイミド樹脂。
- 前記式(1)で表される芳香族アミン樹脂または前記式(2)で表される芳香族アミン樹脂の重量平均分子量が300〜700である請求項1乃至5のいずれか一項に記載のマレイミド樹脂。
- 請求項1乃至6のいずれか一項に記載のマレイミド樹脂を含有する硬化性樹脂組成物。
- 請求項7に記載の硬化性樹脂組成物を硬化して得られる硬化物。
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