JPWO2019198607A1 - Alkenyl group-containing compound, curable resin composition and cured product thereof - Google Patents
Alkenyl group-containing compound, curable resin composition and cured product thereof Download PDFInfo
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- JPWO2019198607A1 JPWO2019198607A1 JP2020513230A JP2020513230A JPWO2019198607A1 JP WO2019198607 A1 JPWO2019198607 A1 JP WO2019198607A1 JP 2020513230 A JP2020513230 A JP 2020513230A JP 2020513230 A JP2020513230 A JP 2020513230A JP WO2019198607 A1 JPWO2019198607 A1 JP WO2019198607A1
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- resin composition
- alkenyl group
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 61
- 125000003342 alkenyl group Chemical group 0.000 title claims abstract description 45
- 239000011342 resin composition Substances 0.000 title claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000000962 organic group Chemical group 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 19
- 239000007870 radical polymerization initiator Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- -1 etc.) Substances 0.000 description 59
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000002904 solvent Substances 0.000 description 25
- 229920000647 polyepoxide Polymers 0.000 description 20
- 239000003822 epoxy resin Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000007795 chemical reaction product Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 239000004065 semiconductor Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000004643 cyanate ester Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000004744 fabric Substances 0.000 description 8
- 150000002366 halogen compounds Chemical class 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 7
- WHGXZPQWZJUGEP-UHFFFAOYSA-N 2-prop-1-enylphenol Chemical compound CC=CC1=CC=CC=C1O WHGXZPQWZJUGEP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- BWQOPMJTQPWHOZ-UHFFFAOYSA-N (2,3-difluorophenyl)-phenylmethanone Chemical compound FC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1F BWQOPMJTQPWHOZ-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000006266 etherification reaction Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 5
- 239000005770 Eugenol Substances 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000004891 communication Methods 0.000 description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- 229960002217 eugenol Drugs 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 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 5
- 239000012535 impurity Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004918 carbon fiber reinforced polymer Substances 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000008393 encapsulating agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000005011 phenolic resin Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000002759 woven fabric Substances 0.000 description 4
- BVKSYBQAXBWINI-LQDRYOBXSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-3-hydroxypropanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]propanoy Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CCCN=C(N)N BVKSYBQAXBWINI-LQDRYOBXSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 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 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000011810 insulating material Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000004780 naphthols Chemical class 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-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
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003192 poly(bis maleimide) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WLVWUJYFJWGNHS-UHFFFAOYSA-N (2,6-dimethyl-4-propylphenyl) cyanate Chemical compound CCCC1=CC(C)=C(OC#N)C(C)=C1 WLVWUJYFJWGNHS-UHFFFAOYSA-N 0.000 description 1
- BTFQDVSPLSTAFG-UHFFFAOYSA-N (2-bromophenyl)-(3-bromophenyl)methanone Chemical compound BrC1=CC=CC(C(=O)C=2C(=CC=CC=2)Br)=C1 BTFQDVSPLSTAFG-UHFFFAOYSA-N 0.000 description 1
- UVBUYAPAJGPEMU-UHFFFAOYSA-N (2-bromophenyl)-(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1Br UVBUYAPAJGPEMU-UHFFFAOYSA-N 0.000 description 1
- ZOEYPNHFGDABED-UHFFFAOYSA-N (2-chlorophenyl)-(3-chlorophenyl)methanone Chemical compound ClC1=CC=CC(C(=O)C=2C(=CC=CC=2)Cl)=C1 ZOEYPNHFGDABED-UHFFFAOYSA-N 0.000 description 1
- YXMYPHLWXBXNFF-UHFFFAOYSA-N (2-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1Cl YXMYPHLWXBXNFF-UHFFFAOYSA-N 0.000 description 1
- SGTSFZMOEFGUPQ-UHFFFAOYSA-N (2-fluorophenyl)-(3-fluorophenyl)methanone Chemical compound FC1=CC=CC(C(=O)C=2C(=CC=CC=2)F)=C1 SGTSFZMOEFGUPQ-UHFFFAOYSA-N 0.000 description 1
- LKFIWRPOVFNPKR-UHFFFAOYSA-N (2-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1F LKFIWRPOVFNPKR-UHFFFAOYSA-N 0.000 description 1
- LWCSOEHZBRTOKR-UHFFFAOYSA-N (2-iodophenyl)-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)C1=CC=CC=C1I LWCSOEHZBRTOKR-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- HCXVPNKIBYLBIT-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOOC(C)(C)C HCXVPNKIBYLBIT-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
- ZHJZMUSEZIVLML-UHFFFAOYSA-N (3-bromophenyl)-(4-bromophenyl)methanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC(Br)=C1 ZHJZMUSEZIVLML-UHFFFAOYSA-N 0.000 description 1
- XFTXWDDQIXYAGY-UHFFFAOYSA-N (3-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC(Cl)=C1 XFTXWDDQIXYAGY-UHFFFAOYSA-N 0.000 description 1
- ZHUXSAKDWNNBCQ-UHFFFAOYSA-N (3-fluorophenyl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC(F)=C1 ZHUXSAKDWNNBCQ-UHFFFAOYSA-N 0.000 description 1
- RGAJXXNLLLIDET-UHFFFAOYSA-N (3-iodophenyl)-(4-iodophenyl)methanone Chemical compound C1=CC(I)=CC=C1C(=O)C1=CC=CC(I)=C1 RGAJXXNLLLIDET-UHFFFAOYSA-N 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical class C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Chemical class CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- OYIYZYBQAKULCH-UHFFFAOYSA-N cyanic acid Chemical compound N#CO.N#CO OYIYZYBQAKULCH-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000004090 cyclononenyl group Chemical group C1(=CCCCCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 229910052839 forsterite Inorganic materials 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical class O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006122 polyamide resin 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
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- 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
- 239000011029 spinel Substances 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 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
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000004804 winding Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and 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 an aromatic carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
Abstract
下記式(1)で表されるアルケニル基含有化合物であり、下記式(1)中のXのHansen溶解度パラメータの極性項δP値が6以上であるアルケニル基含有化合物。【化1】(式(1)中、Xは任意の有機基を表す。Yはアルケニル基を表し、Yが複数存在する場合、それらは同一であっても異なっていてもよい。Zは水素原子、炭素数1〜15の炭化水素基、または炭素数1〜15のアルコキシ基を表し、Zが複数存在する場合、それらは同一であっても異なっていてもよい。lは1〜6の自然数を表す。mおよびnはそれぞれ0以上の整数であり、m+n=1〜5を満たし、l個あるmのうち少なくとも1つは1以上である。)An alkenyl group-containing compound represented by the following formula (1), wherein the polar term δP value of the Hansen solubility parameter of X in the following formula (1) is 6 or more. [Chemical formula 1] (In formula (1), X represents an arbitrary organic group. Y represents an alkoxy group, and when a plurality of Ys are present, they may be the same or different. Z is a hydrogen. Represents an atom, a hydrocarbon group having 1 to 15 carbon atoms, or an alkoxy group having 1 to 15 carbon atoms, and when a plurality of Z's are present, they may be the same or different. L is 1 to 6 Represents a natural number. M and n are integers of 0 or more, respectively, satisfy m + n = 1 to 5, and at least one of l m is 1 or more.)
Description
本発明は、アルケニル基含有化合物、硬化性樹脂組成物及びその硬化物に関するものであり、半導体素子用封止材、液晶表示素子用封止材、有機EL素子用封止材、プリント配線基板、ビルドアップ積層板等の電気・電子部品や炭素繊維強化プラスチック、ガラス繊維強化プラスチック等の軽量高強度構造材用複合材料に好適に使用される。 The present invention relates to an alkenyl group-containing compound, a curable resin composition and a cured product thereof, and relates to a sealing material for a semiconductor element, a sealing material for a liquid crystal display element, a sealing material for an organic EL element, a printed wiring substrate, and the like. It is suitably used for electric / electronic parts such as build-up laminates and composite materials for lightweight and high-strength structural materials such as carbon fiber reinforced plastics and glass fiber reinforced plastics.
近年、電気・電子部品を搭載する積層板は、その利用分野の拡大により、要求特性が広範かつ高度化している。従来の半導体チップは金属製のリードフレームに搭載されることが主流であったが、中央処理装置(以下、CPUと表す。)などの処理能力の高い半導体チップは高分子材料で作られる積層板に搭載されることが多くなってきている。CPU等の素子の処理速度の高速化が進み、クロック周波数が高くなるにつれ、信号伝搬遅延や伝送損失が問題となっていることから、積層板は、低誘電率化、低誘電正接化が求められている。また、素子の処理速度の高速化に伴い、チップの発熱が大きくなるため、耐熱性の向上も同時に求められている。 In recent years, the required characteristics of laminated plates on which electrical and electronic components are mounted have become widespread and sophisticated due to the expansion of their fields of use. Conventional semiconductor chips are mainly mounted on metal lead frames, but semiconductor chips with high processing capacity such as central processing units (hereinafter referred to as CPUs) are laminated plates made of polymer materials. It is becoming more and more installed in. As the processing speed of elements such as CPUs increases and the clock frequency increases, signal propagation delay and transmission loss become problems. Therefore, the laminated board is required to have a low dielectric constant and a low dielectric loss tangent. Has been done. Further, as the processing speed of the element is increased, the heat generated by the chip is increased, so that the heat resistance is also required to be improved at the same time.
特にスマートフォンなどに使用されている半導体パッケージ(以下、PKGと表す。)の小型化、薄型化および高密度化に伴い、PKG基板の薄型化が求められているが、PKG基板が薄くなると、剛性が低下するため、PKGをマザーボード(PCB)に半田実装する際の加熱によって、大きな反りが発生するなど不具合が発生する。これを低減するために、半田実装温度以上の高Tg(例えば、260℃以上、近年では288℃以上)のPKG基板材料が求められている。 In particular, with the miniaturization, thinning, and high density of semiconductor packages (hereinafter referred to as PKG) used for smartphones and the like, it is required to reduce the thickness of the PKG substrate. However, when the PKG substrate becomes thin, the rigidity is increased. Therefore, a problem such as a large warp occurs due to heating when the PKG is solder-mounted on the motherboard (PCB). In order to reduce this, a PKG substrate material having a high Tg (for example, 260 ° C. or higher, and in recent years, 288 ° C. or higher) having a solder mounting temperature or higher is required.
また、一方で近年の大容量・高速通信化に伴い、情報通信機器で扱う電気信号の周波数は年々高くなる傾向にあるが、信号周波数が高くなるほど、電気信号が回路中で熱に変換されるため、伝送損失が増加し、信号を効率よく伝送することが難しくなる。これを低減するために、誘電正接が低い基板材料も求められている。 On the other hand, with the recent increase in capacity and high-speed communication, the frequency of electric signals handled by information and communication equipment tends to increase year by year, but the higher the signal frequency, the more the electric signal is converted into heat in the circuit. Therefore, the transmission loss increases, and it becomes difficult to efficiently transmit the signal. In order to reduce this, a substrate material having a low dielectric loss tangent is also required.
特に現在開発が加速している第5世代通信システム「5G」では、スマートフォンをはじめとした様々な機器のデータ通信において、さらなる大容量化と高速通信が進むことが予想されている。低誘電正接材料のニーズがますます高まってきており、少なくとも1GHzで0.005以下の誘電正接が求められており、この耐熱性、誘電特性(誘電正接)を達成できる材料が求められている。更に、自動車分野においては電子化が進み、エンジン駆動部付近に精密電子機器が配置されることもあるため、より高水準での耐熱・耐湿性が求められる。加えて、電車やエアコン等にはSiC半導体が使用され始めており、半導体素子の封止材には極めて高い耐熱性が要求されるため、従来のエポキシ樹脂封止材では対応できなくなっている。 In particular, in the 5th generation communication system "5G" whose development is currently accelerating, it is expected that the data communication of various devices such as smartphones will be further increased in capacity and high-speed communication. The need for a low dielectric loss tangent material is increasing more and more, and a dielectric loss tangent of 0.005 or less at at least 1 GHz is required, and a material capable of achieving this heat resistance and dielectric property (dielectric loss tangent) is required. Further, in the field of automobiles, digitization is progressing, and precision electronic devices may be arranged near the engine drive unit, so that a higher level of heat resistance and moisture resistance is required. In addition, SiC semiconductors have begun to be used in trains, air conditioners, and the like, and extremely high heat resistance is required for the encapsulant for semiconductor elements, so that conventional epoxy resin encapsulants cannot cope with this.
しかしながら、特許文献1は全てプロペニル基で置換されたフェノール樹脂を用いているため、電気特性が不十分である。また特許文献2では全てアリル基で置換されたフェノール樹脂を用いているため反応性に乏しく、耐熱性の観点から性能として満足できるものとは言い難く、高い耐熱性と電気特性を両立できる材料や硬化系の開発が望まれている。 However, since Patent Document 1 uses a phenol resin substituted with a propenyl group, its electrical properties are insufficient. Further, in Patent Document 2, since all phenol resins substituted with allyl groups are used, the reactivity is poor, and it is difficult to say that the performance is satisfactory from the viewpoint of heat resistance. Development of a curing system is desired.
本発明は、このような状況を鑑みてなされたものであり、溶剤溶解性に優れ、硬化させた場合に優れた耐熱性と電気特性を示すアルケニル基含有化合物、当該化合物を含む硬化性樹脂組成物及びその硬化物を提供することを目的とする。 The present invention has been made in view of such a situation, and has an alkenyl group-containing compound having excellent solvent solubility and excellent heat resistance and electrical properties when cured, and a curable resin composition containing the compound. It is an object of the present invention to provide a product and a cured product thereof.
本発明者等は上記課題を解決するため誠心誠意検討した結果、特定のアルケニル基含有化合物が溶媒溶解性に優れ、その硬化物が耐熱性、電気特性に優れることを見出し、本発明を完成させるに至った。
すなわち本発明は、以下の[1]〜[6]に関する。As a result of sincere studies to solve the above problems, the present inventors have found that a specific alkenyl group-containing compound has excellent solvent solubility and the cured product has excellent heat resistance and electrical properties, and completes the present invention. It came to.
That is, the present invention relates to the following [1] to [6].
[1]
下記式(1)で表されるアルケニル基含有化合物。[1]
An alkenyl group-containing compound represented by the following formula (1).
(式(1)中、Xは任意の有機基を表す。Yはアルケニル基を表し、Yが複数存在する場合、それらは同一であっても異なっていてもよい。Zは水素原子、炭素数1〜15の炭化水素基、または炭素数1〜15のアルコキシ基を表し、Zが複数存在する場合、それらは同一であっても異なっていてもよい。lは1〜6の自然数を表す。mおよびnはそれぞれ0以上の整数であり、m+n=1〜5を満たし、l個あるmのうち少なくとも1つは1以上である。XのHansen溶解度パラメータの極性項δP値は6以上である。)
[2]
前記式(1)中のXのHansen溶解度パラメータの水素結合項δH値が4以上である、前項[1]に記載のアルケニル基含有化合物。
[3]
前記式(1)中のXが下記式(2−1)〜式(2−3)で表される構造のいずれか1種を含有する、前項[1]又は[2]に記載のアルケニル基含有化合物。(In the formula (1), X represents an arbitrary organic group. Y represents an alkoxy group, and when a plurality of Ys are present, they may be the same or different. Z is a hydrogen atom and the number of carbon atoms. It represents a hydrocarbon group of 1 to 15 or an alkoxy group having 1 to 15 carbon atoms, and when a plurality of Z's are present, they may be the same or different. L represents a natural number of 1 to 6. m and n are integers of 0 or more, respectively, satisfy m + n = 1 to 5, and at least one of the l m is 1 or more. The polar term δP value of the Hansen solubility parameter of X is 6 or more. .)
[2]
The alkenyl group-containing compound according to the preceding item [1], wherein the hydrogen bond term δH value of the Hansen solubility parameter of X in the formula (1) is 4 or more.
[3]
The alkenyl group according to the preceding item [1] or [2], wherein X in the formula (1) contains any one of the structures represented by the following formulas (2-1) to (2-3). Containing compound.
(式(2−1)〜式(2−3)中、*は式(1)の酸素原子への結合を表す。)
[4]
前項[1]〜[3]のいずれか一項に記載のアルケニル基含有化合物と、マレイミド樹脂とを含有する、硬化性樹脂組成物。
[5]
さらに、ラジカル重合開始剤を含有する、前項[4]に記載の硬化性樹脂組成物。
[6]
前項[4]又は[5]に記載の硬化性樹脂組成物を硬化させた、硬化物。(In formulas (2-1) to (2-3), * represents the bond of formula (1) to the oxygen atom.)
[4]
A curable resin composition containing the alkenyl group-containing compound according to any one of the above items [1] to [3] and a maleimide resin.
[5]
The curable resin composition according to the preceding item [4], further containing a radical polymerization initiator.
[6]
A cured product obtained by curing the curable resin composition according to the preceding item [4] or [5].
本発明のアルケニル基含有化合物を用いた硬化性樹脂組成物は優れた硬化性を有し、その硬化物は電気特性、耐熱性に優れる。また、本発明のアルケニル基含有化合物は、マレイミド基との反応性が高く、フェノール性水酸基に起因する電気特性の低下はほとんどない。そのため、電気電子部品用絶縁材料(高信頼性半導体封止材料など)及び積層板(プリント配線板、ボールグリッドアレイ(BGA)基板、ビルドアップ基板など)、液晶封止材、有機EL封止材、接着剤(導電性接着剤等)や炭素繊維強化プラスチック(CFRP)を始めとする各種複合材料、塗料等の用途に用いることができる。 The curable resin composition using the alkenyl group-containing compound of the present invention has excellent curability, and the cured product has excellent electrical properties and heat resistance. Further, the alkenyl group-containing compound of the present invention has high reactivity with a maleimide group, and there is almost no deterioration in electrical properties due to the phenolic hydroxyl group. Therefore, insulating materials for electrical and electronic components (highly reliable semiconductor encapsulation materials, etc.), laminated plates (printed wiring boards, ball grid array (BGA) substrates, build-up substrates, etc.), liquid crystal encapsulants, organic EL encapsulants, etc. , Various composite materials such as adhesives (conductive adhesives, etc.) and carbon fiber reinforced plastics (CFRP), paints, etc. can be used.
以下、本発明について詳細に説明する。
本発明のアルケニル基含有化合物は、下記式(1)で表される。
なお、本明細書において、「〜」は上下限を含む範囲を表す(例えば、1〜3としたときは1以上3以下を表す)。Hereinafter, the present invention will be described in detail.
The alkenyl group-containing compound of the present invention is represented by the following formula (1).
In addition, in this specification, "~" represents a range including upper and lower limits (for example, when it is 1 to 3 it represents 1 or more and 3 or less).
式(1)中、Yはアルケニル基を表し、Yが複数存在する場合、それらは同一であっても異なっていてもよい。Yのアルケニル基としては、特に限定はされないが、電気特性と硬化性の観点から、炭素数1〜5のアルケニル基が好ましく、炭素数1〜3のアルケニル基がより好ましく、アリル基、メタリル基、1−プロペニル基、又は2−メチルプロペニル基がさらに好ましく、アリル基または1−プロペニル基が特に好ましい。
Zは水素原子、炭素数1〜15の炭化水素基、または炭素数1〜15のアルコキシ基を表し、Zが複数存在する場合、それらは同一であっても異なっていてもよい。Zは、電気特性の観点から、水素原子、炭素数1〜10の炭化水素基、又は炭素数1〜10のアルコキシ基が好ましく、より好ましくは水素原子、炭素数1〜6の炭化水素基、又は炭素数1〜6のアルコキシ基である。
lは1〜6の自然数を表す。mおよびnはそれぞれ0以上の整数であり、m+n=1〜5を満たし、l個あるmのうち少なくとも1つは1以上である。)In formula (1), Y represents an alkenyl group, and when a plurality of Ys are present, they may be the same or different. The alkenyl group of Y is not particularly limited, but from the viewpoint of electrical properties and curability, an alkenyl group having 1 to 5 carbon atoms is preferable, an alkenyl group having 1 to 3 carbon atoms is more preferable, and an allyl group and a metalyl group are preferable. , 1-propenyl group, or 2-methylpropenyl group is more preferable, and allyl group or 1-propenyl group is particularly preferable.
Z represents a hydrogen atom, a hydrocarbon group having 1 to 15 carbon atoms, or an alkoxy group having 1 to 15 carbon atoms, and when a plurality of Z's are present, they may be the same or different. From the viewpoint of electrical characteristics, Z is preferably a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, more preferably a hydrogen atom, a hydrocarbon group having 1 to 6 carbon atoms, and the like. Alternatively, it is an alkoxy group having 1 to 6 carbon atoms.
l represents a natural number from 1 to 6. m and n are integers of 0 or more, respectively, satisfy m + n = 1 to 5, and at least one of the l m is 1 or more. )
式(1)中、Xは任意の有機基を表す。Xは有機基であれば特に限定されないが、好ましい構造として、下記式(2−1)〜下記式(2−3)で表される構造が挙げられる。 In formula (1), X represents any organic group. X is not particularly limited as long as it is an organic group, but preferred structures include structures represented by the following formulas (2-1) to (2-3).
式(2−1)〜式(2−3)中、*は式(1)の酸素原子への結合を表す。
式(2−1)〜式(2−3)中、*を2つ有する構造のとき上記式(1)のlは2となり、*を3つ有する構造のとき上記式(1)のlは3となる。In formulas (2-1) to (2-3), * represents the bond of formula (1) to the oxygen atom.
In formulas (2-1) to (2-3), when the structure has two *, l in the above formula (1) is 2, and when the structure has three *, l in the above formula (1) is 2. It becomes 3.
前記式(1)中のXとして、より好ましい構造は、式(2−1)又は式(2−2)で表わされる構造であり、特に好ましい構造は、式(2−2)で表される構造である。 A more preferable structure as X in the formula (1) is a structure represented by the formula (2-1) or the formula (2-2), and a particularly preferable structure is represented by the formula (2-2). It is a structure.
本発明のアルケニル基含有化合物は、Hansen溶解度パラメータを用いて構造設計している。Hansen溶解度パラメータは、Hansen氏が提案する物質の溶解性の予測値であり、δD値はLondon分散力、δP値は極性力、δHは水素結合力を示す(Hansen,Charles. The three dimensional solubility parameter and solvent diffusion coefficient:Their importance in surface coating formulation. Copenhagen:Danish Technical Press,1967.を参照)。
式(1)中、XのHansen溶解度パラメータの極性項δP値としては、6〜25が好ましく、より好ましくは8〜22であり、さらに好ましくは10〜20である。δP値が上記範囲であると、極性溶剤や極性材料との親和性が増して相溶性が良好となる。
δP値が6以上であると、極性材料や極性溶剤への相溶性が向上する。また、δP値が25以下であると、誘電特性が良好となる。
本発明のアルケニル化合物は、高い極性を有していながら、反応性基としてフェノール性水酸基を有さない分子設計としているため、優れた耐熱性、溶剤溶解性、誘電特性を併せ持つ。The alkenyl group-containing compound of the present invention is structurally designed using the Hansen solubility parameter. The Hansen solubility parameter is a predicted value of the solubility of a substance proposed by Mr. Hansen. The δD value indicates the London dispersion force, the δP value indicates the polarity force, and the δH indicates the hydrogen bonding force (Hansen, Charles. The three dimensional solution parameter). And solution diffusion cofficient: Their impact in surface coating formation. Copenhagen: Danish Technical Press, 1967.).
In the formula (1), the polarity term δP value of the Hansen solubility parameter of X is preferably 6 to 25, more preferably 8 to 22, and even more preferably 10 to 20. When the δP value is in the above range, the affinity with the polar solvent and the polar material is increased, and the compatibility is improved.
When the δP value is 6 or more, the compatibility with polar materials and polar solvents is improved. Further, when the δP value is 25 or less, the dielectric property becomes good.
Since the alkenyl compound of the present invention has a molecular design that does not have a phenolic hydroxyl group as a reactive group while having high polarity, it also has excellent heat resistance, solvent solubility, and dielectric properties.
式(1)中、XのHansen溶解度パラメータの水素結合項δH値としては、4〜25が好ましく、より好ましくは6〜22であり、さらに好ましくは8〜20である。δH値が上記範囲にあると、硬化物は剛直性を有するため、電気特性の低下が生じない。 In the formula (1), the hydrogen bond term δH value of the Hansen solubility parameter of X is preferably 4 to 25, more preferably 6 to 22, and even more preferably 8 to 20. When the δH value is in the above range, the cured product has rigidity, so that the electrical characteristics do not deteriorate.
次に、本発明のアルケニル基含有化合物の製造方法について説明する。
まず、本発明のアルケニル基含有化合物は、例えば、下記式(3)のフェノール性水酸基を有する化合物、および任意のハロゲン化合物を原料として製造できる。Next, a method for producing the alkenyl group-containing compound of the present invention will be described.
First, the alkenyl group-containing compound of the present invention can be produced, for example, using a compound having a phenolic hydroxyl group of the following formula (3) and an arbitrary halogen compound as raw materials.
式(3)中、Y、Z、m、nは式(1)と同様である。
式(3)のフェノール性水酸基を有する化合物としては、例えば、2−アリルフェノール、2−メタリルフェノール、2−(2−プロペニル)フェノール、2−(1−プロペニル)フェノール、オイゲノール、イソオイゲノール等が挙げられるが、これに限定されない。In formula (3), Y, Z, m, and n are the same as in formula (1).
Examples of the compound having a phenolic hydroxyl group of the formula (3) include 2-allylphenol, 2-metharylphenol, 2- (2-propenyl) phenol, 2- (1-propenyl) phenol, eugenol, isoeugenol and the like. However, it is not limited to this.
任意のハロゲン化合物としては公知のものであれば如何なるものを用いても良い。好ましくは、前記式(2−1)〜(2−3)で表される構造を分子中に含有するものが挙げられ、例えば、2,2’−ジフルオロジフェニルスルホン、2,3’−ジフルオロジフェニルスルホン、2,4’−ジフルオロジフェニルスルホン、3,3’−ジフルオロジフェニルスルホン、3,4’−ジフルオロジフェニルスルホン、4,4’−ジフルオロジフェニルスルホン、2,2’−ジクロロジフェニルスルホン、2,3’−ジクロロジフェニルスルホン、2,4’−ジクロロジフェニルスルホン、3,3’−ジクロロジフェニルスルホン、3,4’−ジクロロジフェニルスルホン、4,4’−ジクロロジフェニルスルホン、2,2’−ジブロモジフェニルスルホン、2,3’−ジブロモジフェニルスルホン、2,4’−ジブロモジフェニルスルホン、3,3’−ジブロモジフェニルスルホン、3,4’−ジブロモジフェニルスルホン、4,4’−ジブロモジフェニルスルホン、2,2’−ジヨードジフェニルスルホン、2,3’−ジヨードジフェニルスルホン、2,4’−ジヨードジフェニルスルホン、3,3’−ジヨードジフェニルスルホン、3,4’−ジヨードジフェニルスルホン、4,4’−ジヨードジフェニルスルホン、シアヌルフルオライド、シアヌルクロリド、シアヌルブロミド、シアヌルアイオダイド、2,2’−ジフルオロベンゾフェノン、2,3’−ジフルオロベンゾフェノン、2,4’−ジフルオロベンゾフェノン、3,3’−ジフルオロベンゾフェノン、3,4’−ジフルオロベンゾフェノン、4,4’−ジフルオロベンゾフェノン、2,2’−ジクロロベンゾフェノン、2,3’−ジクロロベンゾフェノン、2,4’−ジクロロベンゾフェノン、3,3’−ジクロロベンゾフェノン、3,4’−ジクロロベンゾフェノン、4,4’−ジクロロベンゾフェノン、2,2’−ジブロモベンゾフェノン、2,3’−ジブロモベンゾフェノン、2,4’−ジブロモベンゾフェノン、3,3’−ジブロモベンゾフェノン、3,4’−ジブロモベンゾフェノン、4,4’−ジブロモベンゾフェノン、2,2’−ジヨードベンゾフェノン、2,3’−ジヨードベンゾフェノン、2,4’−ジヨードベンゾフェノン、3,3’−ジヨードベンゾフェノン、3,4’−ジヨードベンゾフェノン、4,4’−ジヨードベンゾフェノン等が挙げられるが、これに限定されるものではない。合成時の原料の反応性と原料の入手しやすさの観点から、フルオライド系化合物、クロライド系化合物、ブロマイド系化合物が好ましく、より好ましくはフルオライド系化合物、クロライド系化合物が挙げられる。 Any known halogen compound may be used. Preferably, the molecule contains the structures represented by the formulas (2-1) to (2-3) in the molecule, and examples thereof include 2,2'-difluorodiphenylsulfone and 2,3'-difluorodiphenyl. Pulmonate, 2,4'-difluorodiphenylsulfone, 3,3′-difluorodiphenylsulfone, 3,4′-difluorodiphenylsulfone, 4,4′-difluorodiphenylsulfone, 2,2′-dichlorodiphenylsulfone, 2,3 ′ -Dichlorodiphenylsulfone, 2,4′-dichlorodiphenylsulfone, 3,3′-dichlorodiphenylsulfone, 3,4′-dichlorodiphenylsulfone, 4,4′-dichlorodiphenylsulfone, 2,2′-dibromodiphenylsulfone , 2,3'-dibromodiphenylsulfone, 2,4′-dibromodiphenylsulfone, 3,3′-dibromodiphenylsulfone, 3,4′-dibromodiphenylsulfone, 4,4′-dibromodiphenylsulfone, 2,2′ -Diodediphenylsulfone, 2,3'-diiododiphenylsulfone, 2,4'-diiododiphenylsulfone, 3,3'-diiododiphenylsulfone, 3,4'-diiododiphenylsulfone, 4,4' -Diodediphenylsulfone, cyanulfluoride, cyanul chloride, cyanurbromid, cyanuriodide, 2,2'-difluorobenzophenone, 2,3'-difluorobenzophenone, 2,4'-difluorobenzophenone, 3,3'-difluoro Benzophenone, 3,4'-difluorobenzophenone, 4,4'-difluorobenzophenone, 2,2'-dichlorobenzophenone, 2,3'-dichlorobenzophenone, 2,4'-dichlorobenzophenone, 3,3'-dichlorobenzophenone, 3,4'-dichlorobenzophenone, 4,4'-dichlorobenzophenone, 2,2'-dibromobenzophenone, 2,3'-dibromobenzophenone, 2,4'-dibromobenzophenone, 3,3'-dibromobenzophenone, 3, 4'-dibromobenzophenone, 4,4'-dibromobenzophenone, 2,2'-diiodobenzophenone, 2,3'-diiodobenzophenone, 2,4'-diiodobenzophenone, 3,3'-diiodobenzophenone, Examples thereof include, but are not limited to, 3,4'-diiodobenzophenone and 4,4'-diiodobenzophenone. From the viewpoint of the reactivity of the raw material at the time of synthesis and the availability of the raw material, a fluoride-based compound, a chloride-based compound, and a bromide-based compound are preferable, and a fluoride-based compound and a chloride-based compound are more preferable.
前記式(3)で表されるフェノール性水酸基を有する化合物、および任意のハロゲン化合物との反応は公知の方法で行うことができ、一般的にアルカリ金属水酸化物等の塩基を用いてハロゲン化合物とフェノール性水酸基を有する化合物を反応させてエーテル化する。
この際、メタノール、イソプロパノール、アセトン、メチルエチルケトン、メチルイソブチルケトン、ジメチルスルホン、ジメチルスルホキシド、ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチル−2−ピロリドン等の極性の高い溶剤を使用することが好ましい。極性溶剤の使用量は通常、原料(フェノール性水酸基を有する化合物と任意のハロゲン化合物)の総量100質量部に対して50〜400質量部、好ましくは70〜300質量部である。またこれらの高極性溶剤は単独で用いても併用しても良く、またトルエン、キシレンなどの極性の低い溶剤を併用しても良い。低極性溶剤の使用量は通常、原料(フェノール性水酸基を有する化合物と任意のハロゲン化合物)の総量100質量部に対して50〜400質量部、好ましくは70〜300質量部である。
より詳細には、フェノール性水酸基含有化合物を前記のジメチルホルムアミドやジメチルスルホキシドなどに溶解させた後、水酸化ナトリウム、水酸化カリウムなどのアルカリ金属水酸化物を添加し、30〜250℃で任意のハロゲン化合物を1〜10時間かけて添加し、その後30〜250℃で1〜30時間反応させる。反応終了後、トルエン、メチルイソブチルケトンなどを加え、副生した塩をろ過、水洗などにより除去し、さらに加熱減圧下でトルエン、メチルイソブチルケトン等の溶媒を留去することにより、本発明のアルケニル基含有化合物を得ることができる。The reaction with the compound having a phenolic hydroxyl group represented by the formula (3) and any halogen compound can be carried out by a known method, and generally, a halogen compound using a base such as an alkali metal hydroxide is used. And a compound having a phenolic hydroxyl group are reacted to form an ether.
At this time, highly polar solvents such as methanol, isopropanol, acetone, methyl ethyl ketone, methyl isobutyl ketone, dimethyl sulfoxide, dimethyl sulfoxide, dimethylformamide, 1,3-dimethyl-2-imidazolidinone, and N-methyl-2-pyrrolidone are used. It is preferable to use it. The amount of the polar solvent used is usually 50 to 400 parts by mass, preferably 70 to 300 parts by mass with respect to 100 parts by mass of the total amount of the raw materials (compound having a phenolic hydroxyl group and any halogen compound). Further, these high-polarity solvents may be used alone or in combination, or low-polarity solvents such as toluene and xylene may be used in combination. The amount of the low-polarity solvent used is usually 50 to 400 parts by mass, preferably 70 to 300 parts by mass with respect to 100 parts by mass of the total amount of the raw materials (compound having a phenolic hydroxyl group and any halogen compound).
More specifically, after dissolving the phenolic hydroxyl group-containing compound in the above-mentioned dimethylformamide, dimethylsulfoxide, etc., an alkali metal hydroxide such as sodium hydroxide, potassium hydroxide, etc. is added, and the temperature is 30 to 250 ° C., which is arbitrary. The halogen compound is added over 1-10 hours and then reacted at 30-250 ° C. for 1-30 hours. After completion of the reaction, toluene, methyl isobutyl ketone, etc. are added, the by-produced salt is removed by filtration, washing with water, etc., and the solvent such as toluene, methyl isobutyl ketone, etc. is distilled off under heating and reduced pressure to distill off the alkenyl of the present invention. A group-containing compound can be obtained.
本発明のアルケニル基含有化合物は、不純物として合成に使用した原料を含有することができる。不純物を全く含有しない場合、溶解性が低下する恐れがある。一方で、不純物を多量に含有している場合では、硬化反応時に残存原料に揮発が起き、臭気や作業委環境への悪影響が懸念される。不純物としては、合成に使用する原料および溶剤等が挙げられるが、これらに限定されるものではない。例えば、前記式(3)で表されるフェノール性水酸基を有する化合物、および合成に使用した任意のハロゲン化合物等が挙げられる。不純物の含有量としては0.0001〜5%が好ましく、より好ましくは0.0001〜3%、さらに好ましくは0.0001〜1%である。 The alkenyl group-containing compound of the present invention can contain a raw material used for synthesis as an impurity. If it does not contain any impurities, the solubility may decrease. On the other hand, when a large amount of impurities are contained, the residual raw material volatilizes during the curing reaction, and there is a concern that the odor and the working environment may be adversely affected. Examples of impurities include, but are not limited to, raw materials and solvents used for synthesis. For example, a compound having a phenolic hydroxyl group represented by the above formula (3), an arbitrary halogen compound used for synthesis, and the like can be mentioned. The content of impurities is preferably 0.0001 to 5%, more preferably 0.0001 to 3%, still more preferably 0.0001 to 1%.
本発明の硬化性樹脂組成物はマレイミド樹脂を含有しても良い。
マレイミド樹脂としては従来公知のマレイミド樹脂を使用することができる。マレイミド樹脂の具体例としては、4,4’−ビスマレイミドジフェニルメタン、ポリフェニルメタンマレイミド、m−フェニレンビスマレイミド、2,2’−ビス〔4−(4−マレイミドフェノキシ)フェニル〕プロパン、3,3’−ジメチル−5,5’−ジエチル−4,4’−ジフェニルメタンビスマレイミド、4−メチル−1,3−フェニレンビスマレイミド、4,4’−ジフェニルエーテルビスマレイミド、4,4’−ジフェニルスルフォンビスマレイミド、1,3−ビス(3−マレイミドフェノキシ)ベンゼン、1,3−ビス(4−マレイミドフェノキシ)ベンゼンなどが挙げられる。溶剤溶解性の観点からポリフェニルメタンマレイミドや日本国特開2009−001783号公報、日本国特開平01−294662号公報に記載されているマレイミド樹脂のような分子量分布を有するマレイミド樹脂が好ましい。これらは単独で用いてもよく、2種以上併用してもよい。マレイミド樹脂の配合量は、前記式(1)で表されるアルケニル基含有化合物に対して、質量比で好ましくは0.5〜5倍、より好ましくは1〜3倍の範囲である。
また、日本国特開2009−001783号公報、日本国特開平01−294662号公報に記載されているマレイミド樹脂は、低吸湿性、難燃性、誘電特性に優れているため特に好ましい。The curable resin composition of the present invention may contain a maleimide resin.
As the maleimide resin, a conventionally known maleimide resin can be used. Specific examples of the maleimide resin include 4,4'-bismaleimide diphenylmethane, polyphenylmethane maleimide, m-phenylene bismaleimide, 2,2'-bis [4- (4-maleimide phenoxy) phenyl] propane, 3,3. '-Dimethyl-5,5'-diethyl-4,4'-diphenylmethanebismaleimide, 4-methyl-1,3-phenylene bismaleimide, 4,4'-diphenylether bismaleimide, 4,4'-diphenylsulphon bismaleimide , 1,3-Bis (3-maleimidephenoxy) benzene, 1,3-bis (4-maleimidephenoxy) benzene and the like. From the viewpoint of solvent solubility, maleimide resins having a molecular weight distribution such as polyphenylmethane maleimide and maleimide resins described in Japanese Patent Application Laid-Open No. 2009-001783 and Japanese Patent Application Laid-Open No. 01-294662 are preferable. These may be used alone or in combination of two or more. The blending amount of the maleimide resin is preferably in the range of 0.5 to 5 times, more preferably 1 to 3 times in terms of mass ratio with respect to the alkenyl group-containing compound represented by the formula (1).
Further, the maleimide resin described in Japanese Patent Application Laid-Open No. 2009-001783 and Japanese Patent Application Laid-Open No. 01-294662 is particularly preferable because it is excellent in low hygroscopicity, flame retardancy and dielectric properties.
本発明の硬化性樹脂組成物において、アルケニル基含有化合物のアルケニル基同士や、アルケニル基とマレイミド基を反応させるために、ラジカル重合開始剤を使用することが好ましい。用い得るラジカル重合開始剤としては、メチルエチルケトンパーオキサイド、アセチルアセトンパーオキサイド等のケトンパーオキサイド類、過酸化ベンゾイル等のジアシルパーオキサイド類、ジクミルパーオキサイド、1,3−ビス−(t−ブチルパーオキシイソプロピル)−ベンゼン等のジアルキルパーオキサイド類、t−ブチルパーオキシベンゾエート、1,1−ジ−t−ブチルパーオキシシクロヘキサン等のパーオキシケタール類、α−クミルパーオキシネオデカノエート、t−ブチルパーオキシネオデカノエート、t−ブチルペルオキシピバレート、1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート、t−アミルパーオキシ−2−エチルヘキサノエート、t−ブチルパーオキシ−2−エチルヘキサノエート、t−アミルパーオキシ−3,5,5−トリメチルヘキサノエート、t−ブチルパーオキシ−3,5,5−トリメチルヘキサノエート、t−アミルパーオキシベンゾエート等のアルキルパーエステル類、ジ−2−エチルヘキシルパーオキシジカーボネート、ビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート、t−ブチルパーオキシイソプロピルカーボネート、1,6−ビス(t−ブチルパーオキシカルボニルオキシ)ヘキサン等のパーオキシカーボネート類、t−ブチルハイドロパーオキサイド、クメンハイドロパーオキサイド、t−ブチルパーオキシオクトエート、ラウロイルパーオキサイド等の有機過酸化物やアゾビスイソブチロニトリル、4,4’−アゾビス(4−シアノ吉草酸)、2,2’−アゾビス(2,4−ジメチルバレロニトリル)等のアゾ系化合物の公知の硬化促進剤が挙げられるが、これらに特に限定されるものではない。ケトンパーオキサイド類、ジアシルパーオキサイド類、ハイドロパーオキサイド類、ジアルキルパーオキサイド類、パーオキシケタール類、アルキルパーエステル類、パーカーボネート類等が好ましく、ジアルキルパーオキサイド類がより好ましい。ラジカル重合開始剤の添加量としては、硬化性樹脂組成物の質量100質量部に対して0.01〜5質量部が好ましく、0.01〜3質量部が特に好ましい。用いるラジカル重合開始剤の量が多いと重合反応時に分子量が十分に伸長しない恐れがある。 In the curable resin composition of the present invention, it is preferable to use a radical polymerization initiator in order to react the alkenyl groups of the alkenyl group-containing compound with each other or the alkenyl group with the maleimide group. Examples of the radical polymerization initiator that can be used include ketone peroxides such as methyl ethyl ketone peroxide and acetylacetone peroxide, diacyl peroxides such as benzoyl peroxide, dicumyl peroxide, and 1,3-bis- (t-butylperoxy). Dialkyl peroxides such as isopropyl) -benzene, t-butylperoxybenzoate, peroxyketals such as 1,1-di-t-butylperoxycyclohexane, α-cumylperoxyneodecanoate, t-butyl Peroxyneodecanoate, t-butylperoxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, t-amylperoxy-2-ethylhexanoate, t- Butylperoxy-2-ethylhexanoate, t-amylperoxy-3,5,5-trimethylhexanoate, t-butylperoxy-3,5,5-trimethylhexanoate, t-amylperoxy Alkyl peresters such as benzoate, di-2-ethylhexyl peroxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxyisopropylcarbonate, 1,6-bis (t-butylper) Oxycarbonyloxy) Peroxy carbonates such as hexane, organic peroxides such as t-butyl hydroperoxide, cumene hydroperoxide, t-butyl peroxyoctate, lauroyl peroxide and azobisisobutyronitrile, 4 , 4'-azobis (4-cyanovaleric acid), 2,2'-azobis (2,4-dimethylvaleronitrile) and other known curing accelerators for azo compounds, but are particularly limited. It's not a thing. Ketone peroxides, diacyl peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, alkyl peroxides, percarbonates and the like are preferable, and dialkyl peroxides are more preferable. The amount of the radical polymerization initiator added is preferably 0.01 to 5 parts by mass, particularly preferably 0.01 to 3 parts by mass, based on 100 parts by mass of the curable resin composition. If the amount of the radical polymerization initiator used is large, the molecular weight may not be sufficiently extended during the polymerization reaction.
本発明の硬化性樹脂組成物においてはエポキシ樹脂を含有させても良い。エポキシ樹脂としては、従来公知のエポキシ樹脂のいずれも使用することができる。エポキシ樹脂の具体例としては、フェノール類と各種アルデヒドとの重縮合物、フェノール類と各種ジエン化合物との重合物、フェノール類とケトン類との重縮合物、ビスフェノール類と各種アルデヒドの重縮合物及びアルコール類等をグリシジル化したグリシジルエーテル系エポキシ樹脂、4−ビニル−1−シクロヘキセンジエポキシドや3,4−エポキシシクロヘキシルメチル−3,4’−エポキシシクロヘキサンカルボキシラートなどを代表とする脂環式エポキシ樹脂、テトラグリシジルジアミノジフェニルメタン(TGDDM)やトリグリシジル−p−アミノフェノールなどを代表とするグリシジルアミン系エポキシ樹脂、グリシジルエステル系エポキシ樹脂等が挙げられるが、これらに限定されるものではない。これらは単独で用いてもよく、2種以上を用いてもよい。
また、フェノール類と、ビスハロゲノメチルアラルキル誘導体またはアラルキルアルコール誘導体とを縮合反応させることにより得られるフェノールアラルキル樹脂を原料とし、エピクロルヒドリンと脱塩酸反応させることにより得られるエポキシ樹脂は、低吸湿性、難燃性、誘電特性に優れているため、エポキシ樹脂として特に好ましい。The curable resin composition of the present invention may contain an epoxy resin. As the epoxy resin, any conventionally known epoxy resin can be used. Specific examples of epoxy resins include polycondensates of phenols and various aldehydes, polymers of phenols and various diene compounds, polycondensations of phenols and ketones, and polycondensates of bisphenols and various aldehydes. Alicyclic epoxies typified by glycidyl ether-based epoxy resins obtained by glycidylizing alcohols, 4-vinyl-1-cyclohexene epoxides, 3,4-epoxycyclohexylmethyl-3,4'-epoxycyclohexanecarboxylate, etc. Examples thereof include, but are not limited to, resins, glycidylamine-based epoxy resins typified by tetraglycidyldiaminodiphenylmethane (TGDDM) and triglycidyl-p-aminophenol, and glycidyl ester-based epoxy resins. These may be used alone or two or more kinds may be used.
Further, an epoxy resin obtained by subjecting a phenol aralkyl resin obtained by a condensation reaction of phenols with a bishalogenomethyl aralkyl derivative or an aralkyl alcohol derivative as a raw material and reacting with epichlorohydrin by dehydroxylation is difficult to absorb moisture. It is particularly preferable as an epoxy resin because it has excellent flammability and dielectric properties.
本発明の硬化性樹脂組成物は、エポキシ樹脂を含有する場合、必要に応じて様々なエポキシ樹脂硬化剤やエポキシ樹脂硬化用の触媒(硬化促進剤)を配合することができる。
エポキシ樹脂硬化剤としては、アミン系化合物、酸無水物系化合物、アミド系化合物、フェノ−ル系化合物、活性エステル樹脂などが使用できる。用いうる硬化剤の具体例としては、ジアミノジフェニルメタン、ジエチレントリアミン、トリエチレンテトラミン、ジアミノジフェニルスルホン、イソホロンジアミン、ジシアンジアミド、リノレン酸の2量体とエチレンジアミンとより合成されるポリアミド樹脂、無水フタル酸、無水トリメリット酸、無水ピロメリット酸、無水マレイン酸、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、無水メチルナジック酸、ヘキサヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、ビスフェノール類、フェノール類(フェノール、アルキル置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、ジヒドロキシナフタレン等)と各種アルデヒドとの重縮合物、フェノール類と各種ジエン化合物との重合物、フェノール類と芳香族ジメチロールとの重縮合物、ビフェノール類及びこれらの変性物、イミダゾ−ル、BF3−アミン錯体、グアニジン誘導体などが挙げられる。
硬化剤として活性エステル樹脂を使用する場合は、フェノールエステル類、チオフェノールエステル類、N−ヒドロキシアミンエステル類、複素環ヒドロキシ化合物のエステル類等の反応活性の高いエステル基を1分子中に2個以上有する化合物が好ましい。当該活性エステル系硬化剤は、カルボン酸化合物及びチオカルボン酸化合物の少なくともいずれかの化合物と、ヒドロキシ化合物及びチオール化合物の少なくともいずれかの化合物との縮合反応によって得られるものが好ましい。特に、耐熱性向上の観点から、カルボン酸化合物とヒドロキシ化合物とから得られる活性エステル系硬化剤が好ましく、カルボン酸化合物とフェノール化合物及びナフトール化合物の少なくともいずれかの化合物とから得られる活性エステル系硬化剤が好ましい。
エポキシ樹脂硬化剤の使用量は、エポキシ基(またはグリシジル基)1当量に対して0.5〜1.5当量が好ましく、0.6〜1.2当量が特に好ましい。エポキシ基1当量に対して、0.5当量に満たない場合、あるいは1.5当量を超える場合、いずれも硬化が不完全となり、良好な硬化物性が得られない恐れがある。When the curable resin composition of the present invention contains an epoxy resin, various epoxy resin curing agents and a catalyst for curing the epoxy resin (curing accelerator) can be blended as needed.
As the epoxy resin curing agent, an amine compound, an acid anhydride compound, an amide compound, a phenol compound, an active ester resin and the like can be used. Specific examples of the curing agent that can be used include a polyamide resin synthesized from a dimer of diaminodiphenylmethane, diethylenetriamine, triethylenetetramine, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, and linolenic acid and ethylenediamine, phthalic anhydride, and trihydride. Merritic acid, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylnadic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, bisphenols, phenols (phenol, alkyl substitution) Phenols, naphthols, alkyl-substituted naphthols, dihydroxybenzene, dihydroxynaphthalene, etc.) and various aldehydes, polycondensates of phenols and various diene compounds, polycondensates of phenols and aromatic dimethylols, biphenols and modified products thereof, imidazo - Le, BF 3 - amine complex, guanidine derivatives.
When an active ester resin is used as a curing agent, two highly reactive ester groups such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds are contained in one molecule. The compound having the above is preferable. The active ester-based curing agent is preferably obtained by a condensation reaction between at least one compound of a carboxylic acid compound and a thiocarboxylic acid compound and at least one compound of a hydroxy compound and a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester-based curing agent obtained from a carboxylic acid compound and a hydroxy compound is preferable, and an active ester-based curing agent obtained from at least one compound of the carboxylic acid compound, a phenol compound and a naphthol compound is preferable. Agents are preferred.
The amount of the epoxy resin curing agent used is preferably 0.5 to 1.5 equivalents, particularly preferably 0.6 to 1.2 equivalents, relative to 1 equivalent of the epoxy group (or glycidyl group). If it is less than 0.5 equivalents or more than 1.5 equivalents with respect to 1 equivalent of the epoxy group, curing may be incomplete and good cured physical properties may not be obtained.
上記エポキシ樹脂硬化用の触媒(硬化促進剤)としては、例えば2−メチルイミダゾール、2−エチルイミダゾール、2−フェニルイミダゾール、2−エチル−4−メチルイミダゾール、2−ウンデシルイミダゾール、1−シアノエチル−2−エチル−4−メチルイミダゾールなどのイミダゾール類、トリエチルアミン、トリエチレンジアミン、2−(ジメチルアミノメチル)フェノール、1,8−ジアザ−ビシクロ(5,4,0)ウンデセン−7、トリス(ジメチルアミノメチル)フェノール、ベンジルジメチルアミン等のアミン類、トリフェニルホスフィン、トリブチルホスフィン、トリオクチルホスフィンなどのホスフィン類などが挙げられる。硬化用の触媒の配合量は、硬化性樹脂組成物の合計100質量部に対して、好ましくは10質量部以下、より好ましくは5質量部以下の範囲である Examples of the catalyst (curing accelerator) for curing the epoxy resin include 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, and 1-cyanoethyl-. Imidazoles such as 2-ethyl-4-methylimidazole, triethylamine, triethylenediamine, 2- (dimethylaminomethyl) phenol, 1,8-diazabicyclo (5,4,0) undecene-7, tris (dimethylaminomethyl) ) Amines such as phenol and benzyldimethylamine, and phosphines such as triphenylphosphine, tributylphosphine and trioctylphosphine can be mentioned. The blending amount of the curing catalyst is preferably in the range of 10 parts by mass or less, more preferably 5 parts by mass or less, based on 100 parts by mass of the total of the curable resin composition.
本発明の硬化性樹脂組成物においてはシアネートエステル樹脂を含有させても良い。本発明の硬化性樹脂組成物に配合し得るシアネートエステル化合物としては従来公知のシアネートエステル化合物を使用することができる。シアネートエステル化合物の具体例としては、フェノール類と各種アルデヒドとの重縮合物、フェノール類と各種ジエン化合物との重合物、フェノール類とケトン類との重縮合物、及びビスフェノール類と各種アルデヒドの重縮合物などをハロゲン化シアンと反応させることにより得られるシアネートエステル化合物が挙げられるが、これらに限定されるものではない。これらは単独で用いてもよく2種以上を用いてもよい。
上記フェノール類としては、フェノール、アルキル置換フェノール、芳香族置換フェノール、ナフトール、アルキル置換ナフトール、ジヒドロキシベンゼン、アルキル置換ジヒドロキシベンゼン、ジヒドロキシナフタレン等が挙げられる。
上記各種アルデヒドとしては、ホルムアルデヒド、アセトアルデヒド、アルキルアルデヒド、ベンズアルデヒド、アルキル置換ベンズアルデヒド、ヒドロキシベンズアルデヒド、ナフトアルデヒド、グルタルアルデヒド、フタルアルデヒド、クロトンアルデヒド、シンナムアルデヒド等が挙げられる。
上記各種ジエン化合物としては、ジシクロペンタジエン、テルペン類、ビニルシクロヘキセン、ノルボルナジエン、ビニルノルボルネン、テトラヒドロインデン、ジビニルベンゼン、ジビニルビフェニル、ジイソプロペニルビフェニル、ブタジエン、イソプレン等が挙げられる。
上記ケトン類としてはアセトン、メチルエチルケトン、メチルイソブチルケトン、アセトフェノン、ベンゾフェノン等が挙げられる。
シアネートエステル化合物の具体例としては、ジシアナートベンゼン、トリシアナートベンゼン、ジシアナートナフタレン、ジシアンートビフェニル、2、2’ービス(4ーシアナートフェニル)プロパン、ビス(4ーシアナートフェニル)メタン、ビス(3,5ージメチルー4ーシアナートフェニル)メタン、2,2’ービス(3,5−ジメチル−4ーシアナートフェニル)プロパン、2,2’ービス(4ーシアナートフェニル)エタン、2,2’ービス(4ーシアナートフェニル)ヘキサフロロプロパン、ビス(4ーシアナートフェニル)スルホン、ビス(4ーシアナートフェニル)チオエーテル、フェノールノボラックシアナート、フェノール・ジシクロペンタジエン共縮合物の水酸基をシアネート基に変換したもの等が挙げられるがこれらに限定されるものではない。
また、日本国特開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。The curable resin composition of the present invention may contain a cyanate ester resin. As the cyanate ester compound that can be blended in the curable resin composition of the present invention, a conventionally known cyanate ester compound can be used. Specific examples of cyanate ester compounds include polycondensates of phenols and various aldehydes, polymers of phenols and various diene compounds, polycondensates of phenols and ketones, and weights of bisphenols and various aldehydes. Examples thereof include, but are not limited to, cyanate ester compounds obtained by reacting a condensate or the like with cyanate cyanate. These may be used alone or in combination of two or more.
Examples of the phenols include phenol, alkyl-substituted phenol, aromatic-substituted phenol, naphthol, alkyl-substituted naphthol, dihydroxybenzene, alkyl-substituted dihydroxybenzene, and dihydroxynaphthalene.
Examples of the various aldehydes include formaldehyde, acetaldehyde, alkylaldehyde, benzaldehyde, alkyl-substituted benzaldehyde, hydroxybenzaldehyde, naphthoaldehyde, glutaraldehyde, phthalaldehyde, crotonaldehyde, cinnamaldehyde and the like.
Examples of the various diene compounds include dicyclopentadiene, terpenes, vinylcyclohexene, norbornadiene, vinylnorbornene, tetrahydroindene, divinylbenzene, divinylbiphenyl, diisopropenylbiphenyl, butadiene, and isoprene.
Examples of the ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone and the like.
Specific examples of the cyanate ester compound include dicyanatobenzene, tricyanatebenzene, dicyanatonaphthalene, dicyantobiphenyl, 2,2'-bis (4-cyanatophenyl) propane, and bis (4-cyanatophenyl). Methane, bis (3,5-dimethyl-4-cyanatophenyl) methane, 2,2'-bis (3,5-dimethyl-4-cyanatophenyl) propane, 2,2'-bis (4-cyanatophenyl) ethane, 2,2'-Bis (4-Cyanatophenyl) hexafluoropropane, bis (4-Cyanatophenyl) sulfone, bis (4-Cyanatophenyl) thioether, phenol novolac cyanate, phenol-dicyclopentadiene cocondensate Examples thereof include those obtained by converting a hydroxyl group into a cyanate group, but the present invention is not limited thereto.
Further, the cyanate ester compound whose synthesis method is described in Japanese Patent Application Laid-Open No. 2005-264154 is particularly preferable as the cyanate ester compound because it is excellent in low hygroscopicity, flame retardancy and dielectric properties.
本発明の硬化性樹脂組成物がシアネート樹脂を含む場合、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本発明の硬化性樹脂組成物に含有させることもできる。触媒は、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。 When the curable resin composition of the present invention contains a cyanate resin, zinc naphthenate, cobalt naphthenate, copper naphthenate, and naphthenic acid are required to tritrate the cyanate group to form a sym-triazine ring. Catalysts such as lead, zinc octylate, tin octylate, lead acetylacetonate, and dibutyltin maleate can also be included in the curable resin composition of the present invention. The catalyst is usually 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 mass of the curable resin composition.
さらに、本発明の硬化性樹脂組成物には、必要に応じて溶融シリカ、結晶シリカ、多孔質シリカ、アルミナ、ジルコン、珪酸カルシウム、炭酸カルシウム、石英粉、炭化珪素、窒化珪素、窒化ホウ素、ジルコニア、窒化アルミニウム、グラファイト、フォルステライト、ステアタイト、スピネル、ムライト、チタニア、タルク、クレー、酸化鉄アスベスト、ガラス粉末等の粉体、またはこれらを球形状あるいは破砕状にした無機充填材を添加することができる。また、特に半導体封止用の硬化性樹脂組成物を得る場合、上記の無機充填材の使用量は、硬化性樹脂組成物中、通常80〜92質量%、好ましくは83〜90質量%の範囲である。 Further, the curable resin composition of the present invention contains, if necessary, molten silica, crystalline silica, porous silica, alumina, zircon, calcium silicate, calcium carbonate, quartz powder, silicon carbide, silicon nitride, boron nitride, zirconia. , Aluminum nitride, graphite, forsterite, steatite, spinel, mulite, titania, talc, clay, iron oxide asbestos, glass powder, etc., or an inorganic filler obtained by spheroidizing or crushing these powders. Can be done. Further, particularly when a curable resin composition for encapsulating a semiconductor is obtained, the amount of the above-mentioned inorganic filler used is usually in the range of 80 to 92% by mass, preferably 83 to 90% by mass in the curable resin composition. Is.
本発明の硬化性樹脂組成物には、必要に応じて公知の添加剤を配合することが出来る。用いうる添加剤の具体例としては、ポリブタジエン及びこの変性物、アクリロニトリル共重合体の変性物、ポリフェニレンエーテル、ポリスチレン、ポリエチレン、ポリイミド、フッ素樹脂、シリコーンゲル、シリコーンオイル、シランカップリング剤のような充填材の表面処理剤、離型剤、カーボンブラック、フタロシアニンブルー、フタロシアニングリーン等の着色剤が挙げられる。これら添加剤の配合量は、硬化性樹脂組成物100質量部に対して、好ましくは1,000質量部以下、より好ましくは700質量部以下の範囲である。 Known additives can be added to the curable resin composition of the present invention, if necessary. Specific examples of the additives that can be used include fillings such as polybutadiene and its modified products, modified products of acrylonitrile copolymers, polyphenylene ethers, polystyrene, polyethylene, polyimides, fluororesins, silicone gels, silicone oils, and silane coupling agents. Examples thereof include surface treatment agents for materials, mold release agents, and colorants such as carbon black, phthalocyanine blue, and phthalocyanine green. The blending amount of these additives is preferably in the range of 1,000 parts by mass or less, more preferably 700 parts by mass or less, with respect to 100 parts by mass of the curable resin composition.
本発明の硬化性樹脂組成物は、有機溶剤を添加してワニス状の組成物(以下、単にワニスという。)とすることができる。溶剤添加により硬化性樹脂組成物の調製時における粘度が下がり、ハンドリング性が向上するとともに、ガラスクロス等の基材への含浸性がより向上する傾向にある。用いられる溶剤としては、例えばγ−ブチロラクトン類、N−メチルピロリドン、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N,N−ジメチルイミダゾリジノン等のアミド系溶剤、テトラメチレンスルフォン等のスルフォン類、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルモノアセテート、プロピレングリコールモノブチルエーテル等のエーテル系溶剤、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン、シクロヘキサノン等のケトン系溶剤、トルエン、キシレンなどの芳香族系溶剤が挙げられる。また、積層板を作成する際は、使用する溶剤の沸点が高すぎると残溶剤として残ってしまう可能性がある。使用する溶剤の沸点としては、200℃以下が好ましく、より好ましくは180℃以下である。溶剤は、得られたワニス中の溶剤を除く固形分濃度が、通常10〜80質量%、好ましくは20〜70質量%となる範囲で使用する。 The curable resin composition of the present invention can be made into a varnish-like composition (hereinafter, simply referred to as varnish) by adding an organic solvent. By adding a solvent, the viscosity of the curable resin composition at the time of preparation is lowered, the handleability is improved, and the impregnation property into a base material such as glass cloth tends to be further improved. Examples of the solvent used include γ-butyrolactones, N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, N, N-dimethylimidazolidinone and other amide solvents, tetramethylene sulfone and the like. Ethereal solvents such as sulfones, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether monoacetate, propylene glycol monobutyl ether, and ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone. Examples include solvents and aromatic solvents such as toluene and xylene. Further, when producing a laminated board, if the boiling point of the solvent used is too high, it may remain as a residual solvent. The boiling point of the solvent used is preferably 200 ° C. or lower, more preferably 180 ° C. or lower. The solvent is used in a range in which the solid content concentration of the obtained varnish excluding the solvent is usually 10 to 80% by mass, preferably 20 to 70% by mass.
本発明の硬化性樹脂組成物の硬化反応として、不飽和二重結合と反応しうる公知の反応全てを適応することができる。例えば、ラジカル重合、ene反応、Diels−Alder反応などが挙げられる。これらの反応を用いて硬化を行った場合、エポキシ基の開環反応を利用する硬化反応とは異なり、硬化過程において極性基が発生しないため、耐熱性の向上に伴う吸水性や電気特性の悪化が少なくて済む。
また、本発明の硬化性樹脂組成物には、任意のアルケニル基含有化合物を組成物中に含有することができる。硬化時には本発明記載のアルケニル化合物と任意のアルケニル基含有化合物との組み合わせによるラジカル重合を利用することができる。任意のアルケニル基としては、置換もしくは無置換の直線状、分岐状または環状のアルケニル基が挙げられ、公知のものであれば特に限定されないが、好ましい具体例としては、ビニル基、プロペニル基、ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、ノネニル基、デセニル基、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、エイコセニル基、シクロプロペニル基、シクロブテニル基、シクロペンテニル基、シクロヘキセニル基、シクロヘプテニル基、シクロオクテニル基、シクロノネニル基、シクロデセニル基、シクロウンデセニル基、シクロドデセニル基、シクロトリデセニル基、シクロテトラデセニル基、シクロペンタデセニル基、シクロヘキサデセニル基、シクロヘプタデセニル基、シクロオクタデセニル基、シクロノナデセニル基、シクロエイコセニル基等が挙げられ、さらにノルボルニル基等の多環式化合物もこの範疇に含まれる。また、任意のアルケニル基としては、C6〜C20の1〜4環のアルケニル基がより好ましい。また、任意のアルケニル基における任意の数の水素原子が、それぞれハロゲン原子、置換もしくは無置換の直線状、分岐状または環状のアルキル基、置換もしくは無置換のアリール基、置換もしくは無置換のヘテロアリール基、置換もしくは無置換の直線状、分岐状または環状のアルケニル基、水酸基、アルコキシ基、アミノ基、シアノ基、カルボニル基、カルボキシル基、エステル基で置換されていてもよい。As the curing reaction of the curable resin composition of the present invention, all known reactions that can react with unsaturated double bonds can be applied. For example, radical polymerization, ene reaction, Diels-Alder reaction and the like can be mentioned. When curing is performed using these reactions, unlike the curing reaction using the ring-opening reaction of epoxy groups, polar groups are not generated in the curing process, so that the water absorption and electrical characteristics deteriorate due to the improvement in heat resistance. Is less.
Further, the curable resin composition of the present invention may contain any alkenyl group-containing compound in the composition. At the time of curing, radical polymerization by a combination of the alkenyl compound described in the present invention and an arbitrary alkenyl group-containing compound can be used. Examples of the arbitrary alkenyl group include substituted or unsubstituted linear, branched or cyclic alkenyl groups, and are not particularly limited as long as they are known, but preferred specific examples thereof include a vinyl group, a propenyl group and butenyl. Group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadesenyl group Cyclopropenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclononenyl group, cyclodecenyl group, cycloundecenyl group, cyclododecenyl group, cyclotridecenyl group, cyclotetradecenyl group, cyclo Examples thereof include a pentadecenyl group, a cyclohexadecenyl group, a cycloheptadecenyl group, a cyclooctadecenyl group, a cyclononadesenyl group, a cycloeicosenyl group, and a polycycle such as a norbornyl group. Formula compounds are also included in this category. As the optional alkenyl group, 1-4 alkenyl ring C 6 -C 20 and more preferably. Also, any number of hydrogen atoms in any alkenyl group are halogen atoms, substituted or unsubstituted linear, branched or cyclic alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryls, respectively. It may be substituted with a group, a substituted or unsubstituted linear, branched or cyclic alkenyl group, a hydroxyl group, an alkoxy group, an amino group, a cyano group, a carbonyl group, a carboxyl group or an ester group.
本発明の硬化性樹脂組成物の調製方法は、公知の方法に従い実施することができるが、これに限定されるものではない。例えば、各成分を均一に混合するだけでも、あるいはプレポリマー化してもよい。具体的には、前記式(1)で表されるアルケニル基含有化合物とマレイミド樹脂とを、触媒の存在下または不存在下、溶剤の存在下または不存在下において加熱することによりプレポリマー化する。同様に、前記式(1)で表されるアルケニル基含有化合物とマレイミド樹脂に、必要によりエポキシ樹脂、アミン化合物、マレイミド系化合物、シアネートエステル化合物、フェノール樹脂、酸無水物化合物及びその他添加剤を追加して、プレポリマー化してもよい。各成分の混合またはプレポリマー化は、溶剤の不存在下では、例えば、押出機、ニーダ、ロールなどを用い、溶剤の存在下では、攪拌装置つきの反応釜などを使用する。 The method for preparing the curable resin composition of the present invention can be carried out according to a known method, but is not limited thereto. For example, each component may be mixed uniformly or prepolymerized. Specifically, the alkenyl group-containing compound represented by the formula (1) and the maleimide resin are prepolymerized by heating in the presence or absence of a catalyst, or in the presence or absence of a solvent. .. Similarly, an epoxy resin, an amine compound, a maleimide-based compound, a cyanate ester compound, a phenol resin, an acid anhydride compound and other additives are added to the alkenyl group-containing compound and maleimide resin represented by the above formula (1), if necessary. Then, it may be prepolymerized. In the absence of a solvent, for example, an extruder, a kneader, a roll, or the like is used for mixing or prepolymerizing each component, and in the presence of a solvent, a reaction kettle with a stirrer or the like is used.
本発明の硬化性樹脂組成物は、例えば、上記各成分を所定の割合で均一に混合することにより得られる。また、例えば、通常130〜180℃で30〜500秒の範囲で本発明の硬化性樹脂組成物を予備硬化し、更に、150〜200℃で2〜15時間の範囲で後硬化することにより、充分な硬化反応が進行し、本発明の硬化物が得られる。又、硬化性樹脂組成物の成分を溶剤等に均一に分散または溶解させ、溶媒を除去した後で、硬化させることもできる。 The curable resin composition of the present invention can be obtained, for example, by uniformly mixing each of the above components at a predetermined ratio. Further, for example, the curable resin composition of the present invention is pre-cured at 130 to 180 ° C. for 30 to 500 seconds, and then post-cured at 150 to 200 ° C. for 2 to 15 hours. A sufficient curing reaction proceeds, and the cured product of the present invention is obtained. It is also possible to uniformly disperse or dissolve the components of the curable resin composition in a solvent or the like, remove the solvent, and then cure.
こうして得られる本発明の硬化性樹脂組成物の硬化物は、耐湿性、耐熱性、高接着性を有する。従って、本発明の硬化性樹脂組成物は、耐湿性、耐熱性、高接着性の要求される広範な分野で用いることが出来る。具体的には、絶縁材料、積層板(プリント配線板、BGA用基板、ビルドアップ基板など)、封止材料、レジスト等あらゆる電気・電子部品用材料として有用である。又、成形材料、複合材料の他、塗料材料、接着剤等の分野にも用いることが出来る。特に半導体封止においては、耐ハンダリフロー性が有益なものとなる。
半導体装置は、本発明の硬化性樹脂組成物で封止されたものを有する。半導体装置としては、例えばDIP(デュアルインラインパッケージ)、QFP(クワッドフラットパッケージ)、BGA(ボールグリッドアレイ)、CSP(チップサイズパッケージ)、SOP(スモールアウトラインパッケージ)、TSOP(シンスモールアウトラインパッケージ)、TQFP(シンクワッドフラットパッケージ)等が挙げられる。The cured product of the curable resin composition of the present invention thus obtained has moisture resistance, heat resistance, and high adhesiveness. Therefore, the curable resin composition of the present invention can be used in a wide range of fields in which moisture resistance, heat resistance, and high adhesiveness are required. Specifically, it is useful as an insulating material, a laminated board (printed wiring board, BGA board, build-up board, etc.), a sealing material, a resist, and other materials for all electrical and electronic components. In addition to molding materials and composite materials, it can also be used in fields such as paint materials and adhesives. Especially in semiconductor encapsulation, solder reflow resistance becomes beneficial.
The semiconductor device has one sealed with the curable resin composition of the present invention. Examples of semiconductor devices include DIP (dual in-line package), QFP (quad flat package), BGA (ball grid array), CSP (chip size package), SOP (small outline package), STOP (thin small outline package), and TQFP. (Syncwad flat package) and the like.
本発明の硬化性樹脂組成物は、加熱溶融し、低粘度化して、ガラス繊維、カ−ボン繊維、ポリエステル繊維、ポリアミド繊維、アルミナ繊維などの強化繊維に含浸させることによりプリプレグを得ることもできる。その具体例としては、例えば、Eガラスクロス、Dガラスクロス、Sガラスクロス、Qガラスクロス、球状ガラスクロス、NEガラスクロス、及びTガラスクロス等のガラス繊維、更にガラス以外の無機物の繊維やポリパラフェニレンテレフタラミド(ケブラー(登録商標)、デュポン株式会社製)、全芳香族ポリアミド、ポリエステル;並びに、ポリパラフェニレンベンズオキサゾール、ポリイミド及び炭素繊維などの有機繊維が挙げられるが、これらに特に限定されない。基材の形状としては、特に限定されないが、例えば、織布、不織布、ロービング、チョップドストランドマットなどが挙げられる。また、織布の織り方としては、平織り、ななこ織り、綾織り等が知られており、これら公知のものから目的とする用途や性能により適宜選択して使用することができる。また、織布を開繊処理したものやシランカップリング剤などで表面処理したガラス織布が好適に使用される。基材の厚さは、特に限定されないが、好ましくは0.01〜0.4mm程度である。
さらに、上記プリプレグを所望の形に裁断し、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。The curable resin composition of the present invention can also be heat-melted, reduced in viscosity, and impregnated with reinforcing fibers such as glass fiber, carbon fiber, polyester fiber, polyamide fiber, and alumina fiber to obtain 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 inorganic fibers and polys other than glass. Paraphenylene terephthalamide (Kevlar®, manufactured by DuPont Co., Ltd.), all aromatic polyamides, polyesters; and organic fibers such as polyparaphenylene benzoxazole, polyimide and carbon fibers, but are particularly limited. Not done. The shape of the base material is not particularly limited, and examples thereof include woven fabrics, non-woven fabrics, rovings, and chopped strand mats. Further, as a weaving method of the woven fabric, plain weave, Nanako weave, twill weave and the like are known, and it is possible to appropriately select and use from these known ones according to the intended use and performance. Further, a woven fabric that has been subjected to fiber opening treatment or a glass woven fabric that has been surface-treated with a silane coupling agent or the like is preferably used. The thickness of the base material is not particularly limited, but is preferably about 0.01 to 0.4 mm.
Further, the prepreg is cut into a desired shape, laminated with copper foil or the like if necessary, and then the curable resin composition is heat-cured while applying pressure to the laminate by a press molding method, an autoclave molding method, a sheet winding molding method, or the like. By doing so, a laminated board for electrical and electronic (printed wiring board) and a carbon fiber reinforcing material can be obtained.
以下、本発明を実施例により詳細に説明する。尚、本発明はこれら実施例に限定されるものではない。
実施例において、Hansen溶解度パラメータは、Hansen Solubility Parameter in Practice(HSPiP)Ver.5.0(Charles M.Hansen)を用いて算出した。
また、実施例において、各物性は以下の条件で測定した。
<融点>
DSCにより測定。吸熱ピークトップの値を融点とした。
装置:Q−2000 TA−instruments社製
モード:M(モジュレート)DSCモード
昇温速度:10℃/min
測定温度範囲:30℃から300℃
<1H−NMR>
装置:JNM−ECS400 日本電子株式会社製Hereinafter, the present invention will be described in detail with reference to Examples. The present invention is not limited to these examples.
In the examples, the Hansen solubility parameter is described in Hansen Solubility Parameter in Practice (HSPiP) Ver. Calculated using 5.0 (Charles M. Hansen).
Moreover, in the Example, each physical property was measured under the following conditions.
<Melting point>
Measured by DSC. The value at the top of the endothermic peak was taken as the melting point.
Equipment: Q-2000 TA-instruments mode: M (modulate) DSC mode heating rate: 10 ° C / min
Measurement temperature range: 30 ° C to 300 ° C
< 1 1 H-NMR>
Equipment: JNM-ECS400 manufactured by JEOL Ltd.
(実施例1)
温度計、冷却管、撹拌機を取り付けたフラスコに、2−アリルフェノール80.5質量部、ジフルオロベンゾフェノン65.5質量部、ジメチルスルホキシド300質量部、炭酸カリウム166質量部を加え、100℃で20時間反応させた。トルエン500質量部を加え、水洗を行い、減圧濃縮することにより、下記式(4)で表される半固形樹脂状のジフルオロベンゾフェノンと2−アリルフェノールのエーテル化反応物(AP−BP)130質量部(収率97%)を得た。
式(4)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は6.7、δH値は4.3である。(Example 1)
Add 80.5 parts by mass of 2-allylphenol, 65.5 parts by mass of difluorobenzophenone, 300 parts by mass of dimethylsulfoxide, and 166 parts by mass of potassium carbonate to a flask equipped with a thermometer, a cooling tube, and a stirrer, and add 20 parts by mass at 100 ° C. Reacted for time. By adding 500 parts by mass of toluene, washing with water, and concentrating under reduced pressure, 130 mass by mass of an etherification reaction product (AP-BP) of semi-solid resin-like difluorobenzophenone and 2-allylphenol represented by the following formula (4). Part (yield 97%) was obtained.
In the formula (4), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 6.7, and the δH value is 4.3.
(実施例2)
温度計、冷却管、撹拌機を取り付けたフラスコに、2−(1−プロペニル)フェノール26.8質量部、ジフルオロベンゾフェノン21.8質量部、ジメチルスルホキシド100質量部、炭酸カリウム55.2質量部を加え、100℃で20時間反応させた。トルエン200質量部を加え、水洗を行い、減圧濃縮することにより、下記式(5)で表されるジフルオロベンゾフェノンと2−(1−プロペニル)フェノールのエーテル化反応物(PP−BP)32.4質量部(収率73%)を得た。得られた反応物の融点は110℃であった。
式(5)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は6.7、δH値は4.3である。(Example 2)
In a flask equipped with a thermometer, a cooling tube, and a stirrer, 26.8 parts by mass of 2- (1-propenyl) phenol, 21.8 parts by mass of difluorobenzophenone, 100 parts by mass of dimethyl sulfoxide, and 55.2 parts by mass of potassium carbonate were placed. In addition, the reaction was carried out at 100 ° C. for 20 hours. By adding 200 parts by mass of toluene, washing with water, and concentrating under reduced pressure, an etherification reaction product (PP-BP) of difluorobenzophenone and 2- (1-propenyl) phenol represented by the following formula (5) is 32.4. A mass portion (yield 73%) was obtained. The melting point of the obtained reaction product was 110 ° C.
In the formula (5), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 6.7, and the δH value is 4.3.
(実施例3)
温度計、冷却管、撹拌機を取り付けたフラスコに、オイゲノール32.8質量部、ジフルオロベンゾフェノン21.8質量部、ジメチルスルホキシド100質量部、炭酸カリウム55.2質量部を加え、100℃で20時間反応させた。トルエン200質量部を加え、水洗を行い、減圧濃縮することにより、下記式(6)で表される半固形樹脂状のジフルオロベンゾフェノンとオイゲノールのエーテル化反応物(Eu−BP)47.4質量部(収率93%)を得た。
式(6)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は6.7、δH値は4.3である。(Example 3)
32.8 parts by mass of Eugenol, 21.8 parts by mass of difluorobenzophenone, 100 parts by mass of dimethyl sulfoxide and 55.2 parts by mass of potassium carbonate were added to a flask equipped with a thermometer, a cooling tube and a stirrer, and the temperature was 100 ° C. for 20 hours. It was reacted. By adding 200 parts by mass of toluene, washing with water, and concentrating under reduced pressure, 47.4 parts by mass of an etherification reaction product (Eu-BP) of semi-solid resin-like difluorobenzophenone and eugenol represented by the following formula (6). (Yield 93%) was obtained.
In the formula (6), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 6.7, and the δH value is 4.3.
(実施例4)
温度計、冷却管、撹拌機を取り付けたフラスコに、シアヌルクロリド15.0質量部、トルエン40.8質量部、ジメチルホルムアミド4.1質量部、2−アリルフェノール32.9質量部、炭酸カリウム67.6質量部を加え、内温を100℃まで昇温した。100℃で6時間反応を行い、放冷後、トルエン200質量部を加え水洗し、減圧濃縮することにより、下記式(7)で表されるシアヌルクロリドと2−アリルフェノールのエーテル化反応物(AP−CC)37.9質量部(収率98%)を得た。得られた反応物の融点は110℃であった。
式(7)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は19.6、δH値は15.2)である。(Example 4)
Cyanuric chloride 15.0 parts by mass, toluene 40.8 parts by mass, dimethylformamide 4.1 parts by mass, 2-allylphenol 32.9 parts by mass, potassium carbonate 67 in a flask equipped with a thermometer, a cooling tube, and a stirrer. .6 parts by mass was added and the internal temperature was raised to 100 ° C. The reaction is carried out at 100 ° C. for 6 hours, and after allowing to cool, 200 parts by mass of toluene is added, the mixture is washed with water, and concentrated under reduced pressure to carry out an etherification reaction product of cyanuric chloride and 2-allylphenol represented by the following formula (7). AP-CC) 37.9 parts by mass (yield 98%) was obtained. The melting point of the obtained reaction product was 110 ° C.
In the formula (7), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 19.6, and the δH value is 15.2).
(実施例5)
温度計、冷却管、撹拌機を取り付けたフラスコに、シアヌルクロリド18.4質量部、トルエン50質量部、ジメチルホルムアミド5.0質量部、2−(1−プロペニル)フェノール40.3質量部、炭酸カリウム82.9質量部を加え、内温を100℃まで昇温した。100℃で6時間反応を行い、放冷後、トルエン200質量部を加え水洗し、減圧濃縮することにより、下記式(8)で表されるシアヌルクロリドと2−(1−プロペニル)フェノールのエーテル化反応物(PP−CC)39.2質量部(収率82%)を得た。得られた反応物の融点は131℃であった。
式(8)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は19.6、δH値は15.2である。(Example 5)
18.4 parts by mass of cyanuric chloride, 50 parts by mass of toluene, 5.0 parts by mass of dimethylformamide, 40.3 parts by mass of 2- (1-propenyl) phenol, carbon dioxide in a flask equipped with a thermometer, a cooling tube, and a stirrer. 82.9 parts by mass of potassium was added, and the internal temperature was raised to 100 ° C. The reaction is carried out at 100 ° C. for 6 hours, and after allowing to cool, 200 parts by mass of toluene is added, the mixture is washed with water, and concentrated under reduced pressure to carry out the ether of cyanuric chloride represented by the following formula (8) and 2- (1-propenyl) phenol. 39.2 parts by mass (yield 82%) of the chemical reaction product (PP-CC) was obtained. The melting point of the obtained reaction product was 131 ° C.
In the formula (8), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 19.6, and the δH value is 15.2.
(実施例6)
温度計、冷却管、撹拌機を取り付けたフラスコに、アセトン100質量部、シアヌルクロリド18.4質量部、オイゲノール49.3質量部を加え撹拌を開始し、内温を30℃まで昇温した。水酸化ナトリウム12.6質量部を1.5時間かけて添加し、30℃で6時間反応を行った。減圧濃縮によりアセトンを取り除いた後、トルエン100gを加え、水洗を行い、減圧濃縮することにより、下記式(9)で表されるシアヌルクロリドとオイゲノールのエーテル化反応物(Eu−CC)47.6質量部(収率84%)を得た。得られた反応物の融点は125℃であった。
式(9)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は19.6、δH値は15.2である。(Example 6)
To a flask equipped with a thermometer, a cooling tube, and a stirrer, 100 parts by mass of acetone, 18.4 parts by mass of cyanul chloride, and 49.3 parts by mass of eugenol were added to start stirring, and the internal temperature was raised to 30 ° C. 12.6 parts by mass of sodium hydroxide was added over 1.5 hours, and the reaction was carried out at 30 ° C. for 6 hours. Acetone is removed by concentration under reduced pressure, 100 g of toluene is added, the mixture is washed with water, and concentrated under reduced pressure to carry out an etherification reaction product (Eu-CC) of cyanuric chloride and eugenol represented by the following formula (9) 47.6. A mass portion (yield 84%) was obtained. The melting point of the obtained reaction product was 125 ° C.
In the formula (9), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 19.6, and the δH value is 15.2.
(合成例1)
温度計、冷却管、撹拌機を取り付けたフラスコに、2−(1−プロペニル)フェノール20.2質量部、ジメチルスルホキシド230質量部、水29.4質量部を加え、撹拌を開始した。水酸化ナトリウム12.3gを1時間かけて分割添加し、内温を70℃へ昇温した。p−ビスクロロメチレンビフェニル18.8質量部を1時間かけて添加し、70℃で2時間反応させた。析出した結晶を濾過で濾別し、下記式(10)で表されるp−ビスクロロメチレンビフェニルと2−(1−プロペニル)フェノールのエーテル化反応物(PP−BCMB)31.3質量部(収率93%)を得た。得られた反応物の融点は164℃であった。
式(10)中、式(1)のXに相当する構造のHansen溶解度パラメータのδP値は1.4、δH値は10.2である。(Synthesis Example 1)
20.2 parts by mass of 2- (1-propenyl) phenol, 230 parts by mass of dimethyl sulfoxide, and 29.4 parts by mass of water were added to a flask equipped with a thermometer, a cooling tube, and a stirrer, and stirring was started. 12.3 g of sodium hydroxide was added in portions over 1 hour, and the internal temperature was raised to 70 ° C. 18.8 parts by mass of p-bischloromethylene biphenyl was added over 1 hour and reacted at 70 ° C. for 2 hours. The precipitated crystals were filtered off by filtration, and 31.3 parts by mass of an etherification reaction product (PP-BCMB) of p-bischloromethylene biphenyl and 2- (1-propenyl) phenol represented by the following formula (10) (PP-BCMB). Yield 93%) was obtained. The melting point of the obtained reaction product was 164 ° C.
In the formula (10), the δP value of the Hansen solubility parameter of the structure corresponding to X in the formula (1) is 1.4, and the δH value is 10.2.
(実施例8〜14、比較例1〜2)
実施例2、4、5、合成例1で得られたアルケニル基含有化合物、マレイミド樹脂、及びラジカル重合開始剤を表1の割合(重量部)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。
比較例2では、各種のエポキシ樹脂、マレイミド樹脂、硬化触媒を表1の割合(重量部)で配合し、ミキシングロールで混練、タブレット化後、トランスファー成形で樹脂成形体を調製し、200℃で2時間、更に220℃で6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以下の項目について測定した結果を表1に示す。(Examples 8 to 14, Comparative Examples 1 to 2)
The alkenyl group-containing compound, maleimide resin, and radical polymerization initiator obtained in Examples 2, 4, and 5 and Synthesis Example 1 were blended in the proportions (parts by weight) shown in Table 1 and heated, melted and mixed in a metal container. It was poured into a mold as it was and cured at 220 ° C. for 2 hours.
Table 1 shows the results of measuring the physical characteristics of the cured product thus obtained for the following items.
In Comparative Example 2, various epoxy resins, maleimide resins, and curing catalysts were mixed at the ratios (parts by weight) shown in Table 1, kneaded with a mixing roll, tableted, and then a resin molded product was prepared by transfer molding at 200 ° C. It was cured for 2 hours and further at 220 ° C. for 6 hours. Table 1 shows the results of measuring the physical characteristics of the cured product thus obtained for the following items.
<耐熱性試験>
・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。
測定装置:TA−instruments製、Q−800
測定温度範囲:30℃〜350℃
昇温速度:2℃/min
試験片サイズ:5mm×50mm×0.8mm)
<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。
<溶剤溶解性>
・アルケニル基含有化合物(マレイミド樹脂と未混合)10.0gとメチルエチルケトン10.0gを冷却器を取り付けた100mlフラスコに秤量して70℃に加温して30分撹拌。30分後、目視にて判定し、アルケニル基含有化合物が溶解していたときを○、アルケニル基含有化合物が溶解しきれず残っているときを×とした。<Heat resistance test>
-Glass transition temperature: The temperature when tan δ is the maximum value measured by a dynamic viscoelasticity tester.
Measuring device: TA-instruments, Q-800
Measurement temperature range: 30 ° C to 350 ° C
Temperature rise rate: 2 ° C / min
Specimen size: 5 mm x 50 mm x 0.8 mm)
<Dielectric constant test / dielectric loss tangent test>
-The test was performed by the hollow resonator perturbation method using a 1 GHz hollow resonator manufactured by Kanto Electronics Co., Ltd. However, the sample size was 1.7 mm in width × 100 mm in length, and the thickness was 1.7 mm.
<Solvent solubility>
-Weigh 10.0 g of an alkenyl group-containing compound (unmixed with maleimide resin) and 10.0 g of methyl ethyl ketone in a 100 ml flask equipped with a cooler, heat to 70 ° C., and stir for 30 minutes. After 30 minutes, it was visually judged, and the case where the alkenyl group-containing compound was dissolved was evaluated as ◯, and the case where the alkenyl group-containing compound was not completely dissolved and remained was evaluated as x.
BMI:4,4’−ビスマレイミドジフェニルメタン(東京化成工業社製)
MIR:日本国特開2009−001783号公報実施例4に記載のマレイミド樹脂
エポキシ樹脂:NC−3000−L(日本化薬社製)
フェノール樹脂:GPH−65(日本化薬社製)
2E4MZ:2−エチル−4−メチルイミダゾール(東京化成工業社製)
DCP:ジクミルパーオキサイド(化薬アクゾ社製)
δP値:前記式(1)中、XのHansen溶解度パラメータの極性項の数値
δH値:前記式(1)中、XのHansen溶解度パラメータの水素結合項の数値BMI: 4,4'-bismaleimidediphenylmethane (manufactured by Tokyo Chemical Industry Co., Ltd.)
MIR: Maleimide resin described in Japanese Patent Application Laid-Open No. 2009-001783, Example 4 Epoxy resin: NC-3000-L (manufactured by Nippon Kayaku Co., Ltd.)
Phenol resin: GPH-65 (manufactured by Nippon Kayaku Co., Ltd.)
2E4MZ: 2-Ethyl-4-methylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.)
DCP: Dicumyl peroxide (manufactured by Kayaku Akzo)
δP value: Numerical value of the polarity term of the Hansen solubility parameter of X in the above formula (1) δH value: Numerical value of the hydrogen bond term of the Hansen solubility parameter of X in the above formula (1)
表1の結果より、本発明のアルケニル基含化合物を用いた実施例4〜8は優れた誘電特性と高い耐熱性を有し、さらに溶剤溶解性にも優れることが確認された。 From the results in Table 1, it was confirmed that Examples 4 to 8 using the alkenyl group-containing compound of the present invention had excellent dielectric properties and high heat resistance, and were also excellent in solvent solubility.
本発明を特定の態様を参照して詳細に説明したが、本発明の精神と範囲を離れることなく様々な変更および修正が可能であることは、当業者にとって明らかである。
なお、本願は、2018年4月9日付で出願された2つの日本国特許出願(特願2018−74455、特願2018−74456)に基づいており、それらの全体が引用により援用される。また、ここに引用されるすべての参照は全体として取り込まれる。Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various modifications and modifications can be made without departing from the spirit and scope of the invention.
This application is based on two Japanese patent applications filed on April 9, 2018 (Japanese Patent Application No. 2018-74455, Japanese Patent Application No. 2018-74456), all of which are incorporated by reference. Also, all references cited here are taken in as a whole.
したがって、本発明のアルケニル基含有化合物は、電気電子部品用絶縁材料(高信頼性半導体封止材料など)、積層板(プリント配線板、BGA用基板、ビルドアップ基板など)、接着剤(導電性接着剤など)、CFRPを始めとする各種複合材料用、及び塗料等の用途に有用である。 Therefore, the alkenyl group-containing compound of the present invention is an insulating material for electrical and electronic parts (highly reliable semiconductor encapsulation material, etc.), a laminated board (printed wiring board, BGA substrate, build-up substrate, etc.), and an adhesive (conductive). It is useful for various composite materials such as adhesives), CFRP, and paints.
Claims (6)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2018074456 | 2018-04-09 | ||
JP2018074456 | 2018-04-09 | ||
JP2018074455 | 2018-04-09 | ||
JP2018074455 | 2018-04-09 | ||
PCT/JP2019/014920 WO2019198607A1 (en) | 2018-04-09 | 2019-04-04 | Alkenyl-group-containing compound, curable resin composition, and cured object obtained therefrom |
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