CN111690001A - Phosphorus-containing vinylbenzyl ether compound, process for producing the same, resin composition, and laminate for circuit board - Google Patents
Phosphorus-containing vinylbenzyl ether compound, process for producing the same, resin composition, and laminate for circuit board Download PDFInfo
- Publication number
- CN111690001A CN111690001A CN202010158621.8A CN202010158621A CN111690001A CN 111690001 A CN111690001 A CN 111690001A CN 202010158621 A CN202010158621 A CN 202010158621A CN 111690001 A CN111690001 A CN 111690001A
- Authority
- CN
- China
- Prior art keywords
- phosphorus
- vinylbenzyl
- ether compound
- group
- vinylbenzyl ether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 vinylbenzyl ether compound Chemical class 0.000 title claims abstract description 154
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 87
- 239000011574 phosphorus Substances 0.000 title claims abstract description 85
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 239000011342 resin composition Substances 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims description 12
- 229920005989 resin Polymers 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000007514 bases Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 229920005992 thermoplastic resin Polymers 0.000 claims description 4
- PUZLEUYZHHMIJL-UHFFFAOYSA-N 1-(4-benzyl-6-oxobenzo[c][1,2]benzoxaphosphinin-6-yl)naphthalene-2,3-diol Chemical compound C(C1=CC=CC=C1)C=1C=CC=C2C=3C=CC=CC3P(OC12)(C1=C(C(=CC2=CC=CC=C12)O)O)=O PUZLEUYZHHMIJL-UHFFFAOYSA-N 0.000 claims description 2
- GNWVUPHZVOCTLO-UHFFFAOYSA-N 1-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)naphthalene-2,3-diol Chemical compound OC=1C(=C(C2=CC=CC=C2C1)P1(OC2=CC=CC=C2C=2C=CC=CC12)=O)O GNWVUPHZVOCTLO-UHFFFAOYSA-N 0.000 claims description 2
- DJMZDDHUCSOZTL-UHFFFAOYSA-N 3-(4-benzyl-6-oxobenzo[c][1,2]benzoxaphosphinin-6-yl)benzene-1,2-diol Chemical compound C(C1=CC=CC=C1)C=1C=CC=C2C=3C=CC=CC3P(OC12)(C1=C(C(=CC=C1)O)O)=O DJMZDDHUCSOZTL-UHFFFAOYSA-N 0.000 claims description 2
- SYMJDLPVWJYRMH-UHFFFAOYSA-N 3-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,2-diol Chemical compound OC1=CC=CC(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1O SYMJDLPVWJYRMH-UHFFFAOYSA-N 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 229920002554 vinyl polymer Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001340 alkali metals Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000002966 varnish Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000434 field desorption mass spectrometry Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- HMDQPBSDHHTRNI-UHFFFAOYSA-N 1-(chloromethyl)-3-ethenylbenzene Chemical compound ClCC1=CC=CC(C=C)=C1 HMDQPBSDHHTRNI-UHFFFAOYSA-N 0.000 description 3
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- WMPGCOIUVFJFMG-UHFFFAOYSA-N 1-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)naphthalene-2,7-diol Chemical compound O1C2=CC=CC=C2C2=CC=CC=C2P1(=O)C1=C(O)C=CC2=CC=C(O)C=C21 WMPGCOIUVFJFMG-UHFFFAOYSA-N 0.000 description 2
- ZRZHXNCATOYMJH-UHFFFAOYSA-N 1-(chloromethyl)-4-ethenylbenzene Chemical compound ClCC1=CC=C(C=C)C=C1 ZRZHXNCATOYMJH-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 2
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000003944 tolyl group Chemical group 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
- 239000008096 xylene Substances 0.000 description 2
- 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GWQOYRSARAWVTC-UHFFFAOYSA-N 1,4-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=C(C(C)(C)OOC(C)(C)C)C=C1 GWQOYRSARAWVTC-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- WQKILXGJWIEVHR-UHFFFAOYSA-N 1-(4-benzyl-6-oxobenzo[c][1,2]benzoxaphosphinin-6-yl)naphthalene-2,7-diol Chemical compound C12=CC(O)=CC=C2C=CC(O)=C1P(C1=CC=CC=C1C1=CC=C2)(=O)OC1=C2CC1=CC=CC=C1 WQKILXGJWIEVHR-UHFFFAOYSA-N 0.000 description 1
- WFCJSNUJPWSKNE-UHFFFAOYSA-N 1-(bromomethyl)-3-ethenylbenzene Chemical compound BrCC1=CC=CC(C=C)=C1 WFCJSNUJPWSKNE-UHFFFAOYSA-N 0.000 description 1
- VTPQLJUADNBKRM-UHFFFAOYSA-N 1-(bromomethyl)-4-ethenylbenzene Chemical compound BrCC1=CC=C(C=C)C=C1 VTPQLJUADNBKRM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- ZBOSOHYDNMSQLO-UHFFFAOYSA-N 2-(4-benzyl-6-oxobenzo[c][1,2]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound C(C1=CC=CC=C1)C=1C=CC=C2C=3C=CC=CC3P(OC12)(C1=C(C=CC(=C1)O)O)=O ZBOSOHYDNMSQLO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MSJIPWGDQODKSK-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)phenyl]phenol Chemical class OC1=CC=CC=C1C1=CC=C(C=2C(=CC=CC=2)O)C=C1 MSJIPWGDQODKSK-UHFFFAOYSA-N 0.000 description 1
- LLOXZCFOAUCDAE-UHFFFAOYSA-N 2-diphenylphosphorylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LLOXZCFOAUCDAE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- HPUOAJPGWQQRNT-UHFFFAOYSA-N pentoxybenzene Chemical compound CCCCCOC1=CC=CC=C1 HPUOAJPGWQQRNT-UHFFFAOYSA-N 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
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- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- PGAPATLGJSQQBU-UHFFFAOYSA-M thallium(i) bromide Chemical compound [Tl]Br PGAPATLGJSQQBU-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/304—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B33/00—Layered products characterised by particular properties or particular surface features, e.g. particular surface coatings; Layered products designed for particular purposes not covered by another single class
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/20—Properties of the layers or laminate having particular electrical or magnetic properties, e.g. piezoelectric
- B32B2307/204—Di-electric
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The present invention provides a vinylbenzyl ether compound having excellent low dielectric characteristics, heat resistance and halogen-free flame retardancy in a cured product, a method for producing the same, and a resin composition and a circuit board laminate using the vinylbenzyl ether compound, which impart excellent cured product characteristics (particularly dielectric characteristics) particularly in printed wiring board applications. The present invention is to make specific phosphorus-containingA phosphorus-containing vinylbenzyl ether compound represented by the following formula (1) obtained by reacting the phenol compound (a) with a vinylbenzyl halide, and a cured product having excellent dielectric characteristics, heat resistance and the like can be obtained by using the resin composition containing the vinylbenzyl ether compound as an essential component and having halogen-free flame retardancy.
Description
Technical Field
The present invention relates to a vinylbenzyl ether compound containing a phosphorus atom in a molecule, and to a flame-retardant resin composition containing the compound as an essential component, particularly to a flame-retardant compound used for a resin composition for producing a copper-clad laminate used for an electronic circuit board, or for applications requiring flame retardancy or heat resistance, such as a sealing material, a molding material, a casting material, an adhesive, an electrical insulating coating material, and a film material used for an electronic component.
Background
Patent document 1 discloses a vinylbenzyl ether of a polyphenol such as bisphenol a or bisphenol S. Further, patent document 2 discloses a vinyl compound having flame retardancy without using a halogen. However, in some applications requiring high characteristics, heat resistance is insufficient.
[ Prior art documents ]
[ patent document ]
[ patent document 1] U.S. Pat. No. 4,116,936
[ patent document 2] Japanese patent laid-open publication No. 2004-331537
Disclosure of Invention
[ problems to be solved by the invention ]
The present invention addresses the problem of providing a vinylbenzyl ether compound which has excellent low dielectric characteristics, heat resistance, and halogen-free flame retardancy in a cured product, and a resin composition using the vinylbenzyl ether compound, a material for a circuit board, and a cured product thereof, which impart excellent cured product characteristics (particularly dielectric characteristics) particularly in printed wiring board applications.
[ means for solving problems ]
As a result of diligent research directed toward vinyl compounds having halogen-free flame retardancy and excellent heat resistance, the present inventors have found that a phosphorus-containing vinyl compound obtained by using a phosphorus-containing phenol compound having a specific structure and performing a reaction under specific reaction conditions is excellent in heat resistance, and have completed the present invention.
That is, the present invention is a phosphorus-containing vinylbenzyl ether compound represented by the following formula (1).
[ solution 1]
In the formula (1), R1A C2-40 hydrocarbon group which may have a hetero atom, R2Each independently represents a hydroxyl group or a vinylbenzyloxy group represented by the formula (2), and X represents a trivalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
The present invention also provides a process for producing a phosphorus-containing vinylbenzyl ether compound, which comprises reacting a vinylbenzyl halide compound in an amount of 2.0 to 4.0 moles per 1 mole of a phosphorus-containing phenol compound represented by the following formula (3) and/or the following formula (4).
[ solution 2]
In the formulae (3) and (4), R1And X is independently from R of said formula (1)1And X is the same.
The phosphorus-containing phenol compound is preferably at least one selected from the group consisting of 10- (dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 8-benzyl-10- (dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, and 8-benzyl-10- (dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide.
The basic compound is preferably used in an amount of 0.5 to 5 moles based on 1 mole of the vinylbenzyl halide.
The present invention also provides a resin composition comprising the phosphorus-containing vinylbenzyl ether compound as an essential component and a thermosetting resin and/or a thermoplastic resin.
The present invention also provides a laminate for an electronic circuit board, which contains the phosphorus-containing vinylbenzyl ether compound as an essential component, and a laminate for an electronic circuit board, which is produced using the resin composition.
[ Effect of the invention ]
The phosphorus-containing vinylbenzyl ether compound of the present invention is flame-retardant without containing halogen, and has excellent cured product properties, particularly excellent dielectric loss tangent. Further, since the resin composition further contains a compound having 3 vinyl groups, the resin composition has good heat resistance, and thus can be applied to a laminate for an electronic circuit board or the like which is particularly required to have excellent heat resistance and dielectric properties.
Drawings
FIG. 1 is a gel permeation chromatogram of the phosphorus-containing vinylbenzyl ether compound obtained in example 1.
FIG. 2 is an infrared absorption spectrum of the phosphorus-containing vinylbenzyl ether compound obtained in example 1.
Detailed Description
The present invention will be described in detail. The phosphorus-containing vinylbenzyl ether compound of the present invention is represented by the formula (1). Further, 1 to 3 vinylbenzyloxy groups represented by the formula (2) are present in 1 molecule, and the average number is 1.5 to 3, preferably 1.7 to 2.9, and more preferably 1.9 to 2.8.
In the formula (1), X is trivalent aromatic hydrocarbon group with 6-20 carbon atoms. Aromatic hydrocarbon groups include: benzene ring group, naphthalene ring group, biphenyl ring group, terphenyl ring group, etc.
The aromatic hydrocarbon group may be unsubstituted or may have an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or an arylalkoxy group having 7 to 12 carbon atoms as a substituent. The alkyl group or alkoxy group having 1 to 6 carbon atoms may be any of straight, branched and cyclic, and examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl, cyclohexyl, methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, isopropoxy, sec-butoxy, tert-butoxy, isopentyloxy, neopentyloxy, tert-pentyloxy, isohexyloxy, cyclopentyloxy, cyclohexyloxy, and the like. Examples of the aryl group or aryloxy group having 6 to 10 carbon atoms include: phenyl, tolyl, ethylphenyl, o-xylyl, propylphenyl, mesityl, naphthyl, indanyl, phenoxy, tolyloxy, ethylphenoxy, xylyloxy, propylphenoxy, mesityloxy, naphthyloxy, and the like. Examples of the aralkyl group or aralkyloxy group having 7 to 11 carbon atoms include: benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, phenethyl, 1-phenylethyl, 2-phenylisopropyl, naphthylmethyl, benzyloxy, methylbenzyloxy, dimethylbenzyloxy, trimethylbenzyloxy, phenethyloxy, 1-phenylethyloxy, 2-phenylisopropyl, naphthylmethyloxy, and the like.
The above X is preferably a benzene ring group, a naphthalene ring group, or an aromatic ring group substituted with a methyl group or a 1-phenylethyl group.
In the formula (1), R1The hydrocarbon group having 2 to 40 carbon atoms, which may have a hetero atom, may be any of a linear, branched, and cyclic group, and is preferably a group having an aromatic ring structure, and particularly preferably a biphenyl structure represented by the following formula (5). In addition, in R1When the aromatic ring structure is present, the aromatic ring may have a substituent having 1 to 10 carbon atoms. Examples of the substituent having 1 to 10 carbon atoms include an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, and an aralkyloxy group having 7 to 10 carbon atoms, and specific examples thereof include the above-mentioned substituents, preferably a methyl group, a cyclohexyl group, a phenyl group, a tolyl group, and a benzyl group, and more preferably a methyl group, a phenyl group, and a benzyl group. Further, as the hetero atom, an oxygen atom and the like may be exemplified, which may be contained between carbons constituting a hydrocarbon chain or a hydrocarbon ring.
[ solution 3]
In the formula (5), R3Each independently a hydrocarbon group having 1 to 10 carbon atoms, and j each independently an integer of 0 to 4, preferably 0 to 2, more preferably 0 or 1. When the substituent is contained, the total number of carbon atoms is 12 to 40.
In the formula (1), R2Each independently represents a hydroxyl group or a vinylbenzyloxy group represented by the formula (2). In the formula (1), one vinylbenzyloxy group is contained, and according to two R2Whether it is a hydroxyl group or a vinylbenzyloxy group, and a compound in which the number of vinylbenzyloxy groups is 1, 2, or 3 as a whole is present.
The ratio of the hydroxyl group of the phosphorus-containing phenol compound as a raw material to the vinylbenzyloxy group can be adjusted by controlling the reaction conditions described later, and R can be adjusted in the obtained phosphorus-containing vinylbenzyl ether compound2The hydroxyl group and vinylbenzyloxy group of (a). For example, if the amount of vinylbenzyl halide used is increased relative to the phosphorus-containing phenol compound of the raw material, the proportion of vinylbenzyl oxy groups increases.
Two R with respect to formula (1)2Preferably at least one is vinylbenzyloxy, especially in phosphorus-containing vinylbenzyl ether compounds of formula (1), two R2The content of each vinylbenzyloxy group (compound having 3 vinylbenzyloxy groups) is preferably 0.5% by mass or more, more preferably 5% by mass or more.
The phosphorus-containing vinylbenzyl ether compound represented by the formula (1) is obtained by reacting a phosphorus-containing phenol compound represented by the formula (3) and/or the formula (4) with a vinylbenzyl halide.
The phosphorus-containing phenol compound represented by the formula (4) has a phosphorus-containing heterocycle and can be obtained by the reaction method described in Japanese patent laid-open Nos. 60-126293, 61-236787 and 05-331179.
Specific examples of the phosphorus-containing phenol compound represented by the formula (4) include: 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide (e.g., HCA-HQ, manufactured by Sansho Co., Ltd.), 10- (2, 7-dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide (e.g., HCA-NQ, manufactured by Sansho Co., Ltd.), 8-benzyl-10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 8-benzyl-10- (2, 7-dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, and the like.
Further, by subjecting water to addition reaction with the phosphorus-containing phenol compound represented by the above formula (4), the ring of the phosphorus-containing heterocycle is opened, and the phosphorus-containing phenol compound represented by the formula (3) corresponding to the compound of the above formula (4) can be obtained.
These phosphorus-containing phenol compounds may be used alone or in combination of two or more, and are not limited thereto.
Examples of the vinylbenzyl halide used in the present invention include: p-vinylbenzyl chloride, m-vinylbenzyl chloride, p-vinylbenzyl bromide, m-vinylbenzyl bromide, and the like, and the compounds are not limited to these compounds, and may be used alone or in combination of two or more. Examples of commercially available products include: CMS-14 (manufactured by AGC Seimichem chemical Co., Ltd., for vinylbenzyl chloride), CMS-P (manufactured by AGC Seimichem chemical Co., Ltd., for a mixture of vinylbenzyl chloride and m-vinylbenzyl chloride), and the like.
The reaction of the phosphorus-containing phenol compound with the vinylbenzyl halide is a reaction of a polyphenol with a vinylbenzyl halide, and can be carried out based on a known method. For example, the following methods are available: the phosphorus-containing phenol compound and the vinylbenzyl halide are reacted by adding or dropping an alkali metal hydroxide in a suitable solvent in a batch manner, and the resulting metal halide is separated by filtration or washing with water. Alternatively, the following method is also available: the phosphorus-containing phenol compound and the alkali metal hydroxide are mixed, the vinylbenzyl halide is added or dropped in batches to react, and the generated metal halide is separated by filtration or washing with water.
The blending ratio of the phosphorus-containing phenol compound and the vinylbenzyl halide is 2.0 to 4.0 mol, preferably 2.2 to 3.8 mol, and more preferably 2.5 to 3.5 mol, based on 1 mol of the phosphorus-containing phenol compound. When the vinylbenzyl halide is less than 2.0 mol based on 1 mol of the phosphorus-containing phenol compound, a polyfunctional compound having 3 vinyl groups is hardly obtained. When the amount exceeds 4.0 mol, the amount of unreacted vinylbenzyl halide remaining increases, or the amount of a polymer obtained by a side reaction increases excessively.
The solvent used in the reaction is not particularly limited, and examples thereof include: hydrocarbons such as hexane, heptane, octane, decane, dimethylbutane, pentene, cyclohexane, methylcyclohexane, benzene, toluene, xylene, ethylbenzene, or the like, alcohols such as methanol, ethanol, propanol, butanol, amyl alcohol, hexanol, methylpentyl alcohol, heptanol, cyclohexanol, benzyl alcohol, furfuryl alcohol, or the like, ethers such as ethyl ether, isopropyl ether, butyl ether, diisoamyl ether, methylphenyl ether, ethylphenyl ether, pentylphenyl ether, ethylbenzyl ether, dioxane, methylfuran, tetrahydrofuran, or the like, ketones such as acetone, methyl ethyl ketone, methyl propyl ketone, methyl butyl ketone, methyl amyl ketone, diethyl ketone, ethyl butyl ketone, dipropyl ketone, cyclohexanone, or methyl cellosolve, methyl cellosolve acetate, ethyl cellosolve, cellosolve acetate, ethylene glycol isopropyl ether, diethylene glycol dimethyl ether, methyl ethyl carbitol, methyl butyl ketone, methyl cellosolve acetate, ethyl cellosolve acetate, ethylene glycol isopropyl ether, diethylene glycol dimethyl ether, methyl ethyl carbitol, and the like, Propylene glycol monomethyl ether, dimethylformamide, dimethylsulfoxide and the like are not limited thereto, and may be used alone or in combination of two or more. In addition, when the metal halide produced is removed by washing with water, it is preferable to use a solvent capable of separating the aqueous layer. For example, there may be mentioned: benzene, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, and the like.
In the present specification, the basic compound refers to a compound which reacts with the halogen of the raw material vinylbenzyl halide to promote the reaction with the phosphorus-containing phenol compound, and includes: and alkaline compounds such as hydroxides of alkali metals including lithium hydroxide, sodium hydroxide, and potassium hydroxide, hydroxides of alkaline earth metals including calcium hydroxide and magnesium hydroxide, and carbonates of alkali metals including sodium carbonate and potassium carbonate. Among them, hydroxides of alkali metals are preferable. Further, these may be used alone or in combination of two or more. The solvent may be used in the form of a solid or a solution such as an aqueous solution, and preferably an aqueous solution. The amount of the basic compound used is 0.5 to 5.0 moles, preferably 1 to 3 moles, and more preferably 1.2 to 2 moles, based on 1 mole of the vinylbenzyl halide. In the case where the amount of the basic compound used is less than 0.5 mol, the reaction does not proceed sufficiently. On the other hand, if it exceeds 5.0 mol, a large amount of acid necessary for neutralization is required, which is not preferable from the economical viewpoint.
In the reaction, a catalyst may also be used as necessary. Examples of the catalyst to be used include: three amines such as benzyl dimethylamine, four ammonium salts such as tetramethyl ammonium chloride and tetramethyl ammonium bromide, phosphines such as triphenyl phosphine and tris (2, 6-dimethoxyphenyl) phosphine, phosphonium salts such as benzyl triphenyl phosphonium chloride, tetrabutyl phosphonium bromide, ethyl triphenyl phosphonium bromide and tetrabutyl phosphonium iodide, and imidazoles such as 2-methylimidazole and 2-ethyl-4-methylimidazole, and these catalysts may be used alone or in combination of two or more. The amount of the catalyst used is 10 parts by mass or less, preferably 5 parts by mass or less, per 100 parts by mass of the raw material.
The reaction temperature is preferably from 30 ℃ to 150 ℃, more preferably from 50 ℃ to 90 ℃. If the reaction temperature is high, polymerization proceeds by reaction of vinyl groups, and if the reaction temperature is too low, the reaction does not proceed and efficiency is poor. Various chromatographic methods or Infrared (IR) spectrum, Ultraviolet (UV) spectrum, etc. can be used for tracing the reaction. For example, the end point can be determined by measuring the residual amount of vinylbenzyl halide of the raw material or the peak value of the functional group involved in the reaction.
In the production process of the present invention, depending on the case where the phosphorus-containing phenol compound represented by the above formula (4) is used as a raw material or the reaction conditions, a phosphorus-containing vinylbenzyl ether compound represented by the following formula (6) may be by-produced.
[ solution 4]
In the formula (6), R1、R2And X is independently from R of said formula (1)1、R2And X is the same.
In the production process of the present invention, the phosphorus-containing phenol compound represented by the formula (3) and/or the formula (4) may be obtained by reacting a phosphorus compound represented by the following formula (7) and/or the formula (8) with a quinone compound, and then reacted with a vinylbenzyl halide compound without isolation and purification. In this case, a reaction product of the residual raw material phosphorus compound and the vinylbenzyl halide may be by-produced.
[ solution 5]
In the formulae (7) and (8), R1And R of the formula (1)1Are the same meaning.
In the reaction product obtained by the production method of the present invention, the compound represented by the formula (6) and the like may be produced as a by-product together with the phosphorus-containing vinylbenzyl ether compound represented by the formula (1) of the present invention, and a mixture of these by-products may be used as long as the effects of the present invention are not impaired. In this case, the content of the by-product is less than 30% by mass, more preferably less than 20% by mass. These by-products may be separated and removed by purifying the reaction product by distillation or the like.
Since the obtained phosphorus-containing vinylbenzyl ether compound has a radical polymerizability of a vinyl group, it is polymerized by light irradiation or heating to obtain a cured product. As shown in formula (1) and formula (2), R2Being vinylbenzyloxy or hydroxy, hydroxy may also be used in the hardening. In addition, a polymerization inhibitor may be added in advance during storage. Examples of the polymerization inhibitor include quinones, p-phenylenediphenols, phenols, various copper salts, amidines, hydrazines, and the like, and furtherExamples of the metal salt include, but are not limited to, toluquinone, hydroquinone, copper naphthenate, and hydrazine hydrochloride, and two or more of these may be used alone or in combination.
In the curable resin composition containing a phosphorus-containing vinylbenzyl ether compound as an essential component, a radical polymerization initiator may be used as needed. Examples of the radical polymerization initiator that can be used include: methyl ethyl ketone peroxide, cyclohexanone peroxide, methyl acetate peroxide, acetylacetone peroxide, cumene hydroperoxide, benzoyl peroxide, t-butyl peroxybenzoate, and the like, and these are not limited to these, and may be used alone, or two or more kinds may be used in combination.
Various other curable resins or thermoplastic resins can be blended in the resin composition of the present invention. Examples of the curable resin include epoxy resins, vinylbenzyl ether compounds other than those of the present invention, and polyester resins, and examples of the thermoplastic resin include polyethylene, polypropylene, acrylonitrile-butadiene-styrene (ABS) resins, polystyrene, methacrylic resins, polycarbonate, polyphenylene oxide, and polyphenylene sulfide, and are not limited to these resins, and they may be used alone or in combination of two or more. In the case where such another resin is used in combination in the curable resin composition containing the phosphorus-containing vinylbenzyl ether compound represented by formula (1) as an essential component, the phosphorus-containing vinylbenzyl ether compound represented by formula (1) is mainly intended to impart flame retardancy, and therefore, the other resin may be used in an amount of less than 1900 parts by mass per 100 parts by mass of the phosphorus-containing vinylbenzyl ether compound represented by formula (1). In other words, in the case of using the phosphorus-containing vinylbenzyl ether compound of the present invention as a flame retardant in a resin composition containing an epoxy resin or the like as a main component, it is sufficient to add 5 mass% or more to the composition (solid component).
In addition, in the resin composition of the present invention, various fillers can be formulated as necessary. Examples of the filler include: aluminum hydroxide, magnesium hydroxide, talc, calcined talc, clay, kaolin, titanium oxide, glass powder, silica balloon, or the like, or glass fiber, pulp fiber, synthetic fiber, ceramic fiber, or the like, and these are not limited to these, and may be used alone, or two or more kinds may be used in combination. Further, a pigment may be blended.
As a result of evaluating the properties of the composition of the present invention, a cured product comprising a resin composition containing, as an essential component, a phosphorus-containing vinylbenzyl ether compound obtained by reacting a phosphorus-containing phenol compound with a vinylbenzyl halide has flame retardancy without containing a halide, and exhibits a low dielectric constant of 3.2 or less, a low dielectric loss tangent of 0.006 or less without dissociating a halogen at a high temperature, and also has excellent heat resistance.
[ examples ]
The present invention will be specifically described with reference to examples and comparative examples, but the present invention is not limited to these examples. Unless otherwise specified, "part" represents part by mass and "%" represents mass%. The measurement methods were carried out by the following methods, respectively. The units of the equivalent are all "g/eq.
Phosphorus content: sulfuric acid, hydrochloric acid, and perchloric acid are added to a sample, and wet ashing is performed to convert all phosphorus atoms into orthophosphoric acid. Metavanadate and molybdate were reacted in an acidic sulfuric acid solution, and the absorbance at 420nm of the resulting phosphovanadomolybdic acid complex was measured, and the phosphorus atom content determined from a calibration curve prepared in advance using potassium dihydrogen phosphate was expressed in% by. The phosphorus content of the laminate is expressed as the content of the resin component in the laminate. Namely, the phosphorus content of the resin composition.
Combustibility: according to UL94 (safety certification specification by Underwriters laboratories inc.). The 5 test pieces were tested, and based on the total time of the flaming combustion durations after the 1 st and 2 nd contact flames (5 contact flames were 2 times each for 10 times in total), the test pieces were determined using the same criteria, i.e., V-0, V-1, and V-2.
Glass transition temperature (Tg): the peak top temperature of tan was measured by a dynamic viscoelasticity measuring apparatus (EXSTAR 6000 DMS6100 manufactured by SII nanotechnology) GmbH under a temperature rise condition of 5 ℃ per minute.
Relative dielectric constant and dielectric loss tangent: the relative dielectric constant and the dielectric loss tangent at a frequency of 1GHz were determined by a capacitance method using a material analyzer (manufactured by Agilent Technologies) according to IPC-TM-6502.5.5.9.
Field Desorption Mass Spectrometry (FD-MS) analysis: dissolved in tetrahydrofuran (manufactured by Kanto chemical Co., Ltd., for high performance liquid chromatography), and measured by a mass spectrometer (manufactured by JMS-T100GCV, manufactured by Japan electronic Co., Ltd.).
GPC (Gel Permation Chromatography): a column (TSKgelG 4000H, manufactured by Tosoh corporation, TSKgelG 4000H) was serially connected to a main body (HLC-8220 GPC, manufactured by Tosoh corporation, Ltd.)XL、TSKgelG3000HXL、TSKgelG2000HXL) And the column temperature was set to 40 ℃. In addition, Tetrahydrofuran (THF) was used as an eluent, and a differential refractive index detector was used as a detector, with a flow rate of 1 mL/min. The measurement sample used was 50. mu.L of a sample obtained by dissolving 0.1g of the sample in 10mL of THF and filtering the solution through a microfilter. The data was processed using GPC-8020 model II version 6.00, manufactured by Tosoh corporation.
IR (infrared absorption spectrum): the cell used was KRS-5, a sample prepared by dissolving in THF was applied to the cell, dried, and the wave number was measured at 650cm after drying, using a Fourier transform type infrared spectrophotometer (manufactured by Perkin Elmer precision, Spectrum-Fourier transform Infrared Spectrometer)1760X-1～4000cm-1Absorbance of (b).
The vinylbenzyl halide, the phosphorus-containing phenol compound, and other materials used in the following examples are as follows.
CMS-P: mixture of p-vinylbenzyl chloride and m-vinylbenzyl chloride (manufactured by AGC seimi chemical Co., Ltd.)
CMS-14: para vinylbenzyl chloride (manufactured by AGC seimi chemical Co., Ltd.)
HCA ═ NQ: 10- (2, 7-Dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanphotochemical Co., Ltd., phosphorus content: 8.3%)
HCA-HQ: 10- (2, 5-dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanphotochemical Co., Ltd., phosphorus content: 9.6%)
HCA: 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (manufactured by Sanphotochemical Ltd., phosphorus content: 14.4%)
NQ: 1, 4-naphthoquinone (4% water-containing product, Kawasaki chemical Co., Ltd.)
TBAB: catalyst, tetrabutylammonium bromide (reagent)
TMAC: catalyst, tetramethylammonium chloride (reagent)
Pabucillu (Perbutyl) P: a radical polymerization initiator, 1, 4-bis [ (t-butylperoxy) isopropyl ] benzene (manufactured by Nippon grease Co., Ltd.)
AO-60: an antioxidant, pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] (manufactured by Addicke (ADEKA) Co., Ltd.)
Example 1
In a reaction apparatus equipped with a stirrer, a thermometer, and a cooling tube, 187 parts of HCA as a phosphorus-containing phenol compound, 244 parts of CMS-P as a vinylbenzyl halide (3.2 moles per 1 mole of the phosphorus-containing phenol compound), 8.6 parts of TBAB as a catalyst, and 162 parts of diethylene glycol dimethyl ether as a solvent were charged, and the temperature was raised to 75 ℃. 392 parts of a 49% aqueous sodium hydroxide solution (3.0 mol based on 1 mol of vinylbenzyl halide) as an alkali metal was added dropwise over 5 hours at 75 ℃. After the completion of the dropwise addition, the reaction was continued until the reaction was sufficiently completed by following the residual amount of vinylbenzyl halide by gas chromatography while keeping the reaction temperature at 75 ℃. Thereafter, the pressure was reduced and the solvent and water were recovered. Toluene 870 parts was added for dilution. 160 parts of ion exchange water is added, and the mixture is neutralized by using 35% hydrochloric acid until the pH value is 5-6. Standing and separating and removing the water layer. And repeatedly washing and cleaning for 3-5 times and separating and removing a water layer. The pressure was reduced at 75 ℃ and the dehydration was carried out under reflux. Filtration is carried out, and then the solvent is recovered. The obtained phosphorus-containing vinylbenzyl ether compound (resin 1) was a dark brown solid substance. The GPC diagram of resin 1 is shown in fig. 1, and the IR diagram is shown in fig. 2. As a result of the FD-MS analysis, 508.2 as a monofunctional vinyl resin, 624.3 as a difunctional vinyl resin, and 740.2 as a trifunctional vinyl resin were confirmed, respectively, and the average number of vinylbenzyloxy groups was 2.0. The phosphorus content was 4.1%.
After 100 parts of the obtained phosphorus-containing vinylbenzyl ether compound was uniformly dissolved in 100 parts of toluene, 0.5 part of perbutylu (Perbutyl) P and 600.2 parts of AO were added to the solution, and uniformly mixed to obtain a varnish of the resin composition.
The obtained varnish of the resin composition was impregnated in glass cloth (manufactured by ritong textile gmbh, WEA7628XS13, 0.18mm thick), and then heated at 130 ℃ for 5 minutes, thereby drying, to obtain a prepreg. Copper foils (HS 1-M2-VSP, thickness 35 μ M, Rz: 1.2 μ M) were superposed on top of and under 8 sheets of the resulting prepreg, and vacuum pressing was performed under 2MPa at 130 ℃ for 130 minutes +210 ℃ for 180 minutes to obtain a laminate having a thickness of 1.6 mm. Both surfaces of the obtained laminate were etched to obtain a test piece for flame retardancy measurement. The glass transition temperature and flame retardancy of the laminate are shown in table 1.
The obtained prepreg was loosened and made into a powdery prepreg powder passing through a 100 mesh sieve. The obtained prepreg powder was put into a fluororesin mold, and vacuum-pressed at 2MPa under a temperature condition of 130 ℃ for 130 minutes +210 ℃ for 180 minutes, to obtain a 50mm square 12mm thick test piece. The results of the relative dielectric constant and the dielectric loss tangent of the test piece are shown in table 1.
Example 2
In the same apparatus as in example 1, 162 parts of HCA-HQ as a phosphorus-containing phenol compound, 7.8 parts of TBAB as a catalyst, and 140 parts of diethylene glycol dimethyl ether as a solvent were charged, and the temperature was raised to 75 ℃. At 75 ℃, 202 parts of a 50% potassium hydroxide aqueous solution (1.2 moles per 1 mole of vinylbenzyl halide) as an alkali metal was added dropwise while paying attention to heat generation. 229 parts of CMS-14 (3.0 moles per 1 mole of the phosphorus-containing phenol compound) as a vinylbenzyl halide was charged over 3 hours while maintaining the reaction temperature at 65 to 75 ℃. After the completion of the charge, the reaction was continued until the reaction was sufficiently completed by tracing the residual amount of vinylbenzyl halide by gas chromatography while keeping the reaction temperature at 75 ℃. Thereafter, the pressure was reduced and the solvent and water were recovered. 785 parts of toluene was added thereto for dilution. 160 parts of ion exchange water is added, and the mixture is neutralized by using 35% hydrochloric acid until the pH value is 5-6. Standing and separating and removing the water layer. And repeatedly washing and cleaning for 3-5 times and separating and removing a water layer. The pressure was reduced at 75 ℃ and the dehydration was carried out under reflux. Filtration is carried out, and then the solvent is recovered. The obtained phosphorus-containing vinylbenzyl ether compound (resin 2) was a pale yellow semi-solid substance. As a result of FD-MS analysis, 458.2 as a monofunctional vinyl resin, 574.2 as a difunctional vinyl resin, and 690.2 as a trifunctional vinyl resin were confirmed, respectively, and the average number of vinylbenzyloxy groups was 1.9. The phosphorus content was 4.6%.
A resin composition varnish, a prepreg, and a laminate were obtained in the same manner as in example 1. The measurement results of the glass transition temperature, flame retardancy, relative dielectric constant, and dielectric loss tangent are shown in table 1.
Example 3
108 parts of HCA and 162 parts of diethylene glycol dimethyl ether were charged into the same apparatus as in example 1, and the temperature was raised to 75 ℃. While paying attention to the exothermic reaction, 55.8 parts of NQ were added in portions. After the reaction was continued at 85 ℃ for 30 minutes, the temperature was raised to 110 ℃ and the reaction was further carried out for 2 hours. The temperature was lowered to 75 ℃, and CMS-P191 parts (2.5 moles per 1 mole of the phosphorus-containing phenol compound produced by the reaction of HCA and NQ) as a vinylbenzyl halide and TBAB 7.1 parts as a catalyst were added and mixed. 205 parts of a 49% aqueous sodium hydroxide solution (2.0 moles per 1 mole of vinylbenzyl halide) as an alkali metal was added dropwise over 5 hours while paying attention to heat generation at 75 ℃. After the completion of the dropwise addition, the reaction was continued until the reaction was sufficiently completed by following the residual amount of vinylbenzyl halide by gas chromatography while keeping the reaction temperature at 75 ℃. Thereafter, the pressure was reduced and the solvent and water were recovered. 830 parts of toluene was added thereto to dilute the mixture. 160 parts of ion exchange water is added, and the mixture is neutralized by using 35% hydrochloric acid until the pH value is 5-6. Standing and separating and removing the water layer. And repeatedly washing and cleaning for 3-5 times and separating and removing a water layer. The pressure was reduced at 75 ℃ and the dehydration was carried out under reflux. Filtration is carried out, and then the solvent is recovered. The obtained phosphorus-containing vinylbenzyl ether compound (resin 3) was a dark brown solid. As a result of the FD-MS analysis, 508.2 as a monofunctional vinyl resin, 624.3 as a difunctional vinyl resin, and 740.2 as a trifunctional vinyl resin were confirmed, respectively, and the average number of vinylbenzyloxy groups was 1.7. The phosphorus content was 4.6%.
A resin composition varnish, a prepreg, and a laminate were obtained in the same manner as in example 1. The measurement results of the glass transition temperature, flame retardancy, relative dielectric constant, and dielectric loss tangent are shown in table 1.
Comparative example 1
A dark brown phosphorus-containing vinylbenzyl ether compound (resin H1) was obtained in a solid state in the same apparatus as in example 1 except that 187 parts of HCA ═ NQ, 114 parts of CMS-14 (1.5 mol based on 1 mol of the phosphorus-containing phenol compound), 6.0 parts of TBAB, 183 parts of a 49% aqueous sodium hydroxide solution (3.0 mol based on 1 mol of the vinylbenzyl halide) and 640 parts of toluene were used as the phosphorus-containing phenol compound. As a result of FD-MS analysis, 508.2 as a monofunctional vinyl resin and 624.3 as a difunctional vinyl resin were confirmed, but 740.2 as a trifunctional vinyl resin was not confirmed. The average number of vinylbenzyloxy groups was 1.4. The phosphorus content was 5.6%.
A resin composition varnish, a prepreg, and a laminate were obtained in the same manner as in example 1. The measurement results of the glass transition temperature, flame retardancy, relative dielectric constant, and dielectric loss tangent are shown in table 1.
Comparative example 2
A phosphorus-containing vinylbenzyl ether compound (resin H2) was obtained in the same manner as in example 2, except that 155 parts of diphenylphosphinyl hydroquinone, which is a phosphorus-containing phenol compound, was used in the same apparatus as in example 1. The phosphorus content is 5.7%
A resin composition varnish, a prepreg, and a laminate were obtained in the same manner as in example 1. The measurement results of the glass transition temperature, flame retardancy, relative dielectric constant, and dielectric loss tangent are shown in table 1.
Comparative example 3
A bromine-containing vinylbenzyl ether compound (resin H3) was obtained in the same manner as in example 2 except that 170 parts of tetrabromobisphenol a, 90 parts of toluene as a reaction solvent, 97.9 parts of CMS-P as a vinylbenzyl halide, 0.9 part of TMAC as a catalyst, and 83.1 parts of a 49% aqueous sodium hydroxide solution as an alkali metal were used instead of the phosphorus-containing phenol compound. The average number of vinylbenzyloxy groups was 2.0. The bromine content was 42%.
A resin composition varnish, a prepreg, and a laminate were obtained in the same manner as in example 1. The measurement results of the glass transition temperature, flame retardancy, relative dielectric constant, and dielectric loss tangent are shown in table 1.
[ Table 1]
As shown in Table 1, the phosphorus-containing vinyl resin of the present invention has flame retardancy without containing halogen, and among the physical properties of the cured product, has excellent dielectric properties, particularly excellent heat resistance.
Claims (7)
1. A phosphorus-containing vinylbenzyl ether compound represented by the following formula (1),
in the formula (1), R1A C2-40 hydrocarbon group which may have a hetero atom, R2Each independently represents a hydroxyl group or a vinylbenzyloxy group represented by the formula (2), and X represents a trivalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
2. A process for producing a phosphorus-containing vinylbenzyl ether compound, which comprises reacting a vinylbenzyl halide in an amount of 2.0 to 4.0 mol per 1 mol of at least one phosphorus-containing phenol compound represented by the following formula (3) or (4),
in the formulae (3) and (4), R1Is a C2-40 hydrocarbon group which may have a hetero atom, and X is a trivalent C6-20 aromatic hydrocarbon group.
3. The process for producing a phosphorus-containing vinylbenzyl ether compound according to claim 2, wherein the phosphorus-containing phenol compound is at least one selected from the group consisting of 10- (dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, 8-benzyl-10- (dihydroxyphenyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide, and 8-benzyl-10- (dihydroxynaphthyl) -10H-9-oxa-10-phosphaphenanthrene-10-oxide.
4. The process for producing a phosphorus-containing vinylbenzyl ether compound according to claim 2 or 3, wherein the basic compound is used in an amount of 0.5 to 5 mol based on 1 mol of the vinylbenzyl halide.
5. A resin composition comprising the phosphorus-containing vinylbenzyl ether compound according to claim 1 as an essential component and at least one of a thermosetting resin and a thermoplastic resin.
6. A laminate for an electronic circuit substrate, which comprises the phosphorus-containing vinylbenzyl ether compound according to claim 1 as an essential component.
7. A laminate for an electronic circuit board, which is produced by using the resin composition according to claim 5.
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| JP2019045766A JP7239357B2 (en) | 2019-03-13 | 2019-03-13 | Phosphorus-containing vinyl benzyl ether compound |
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| CN104211732A (en) * | 2013-05-31 | 2014-12-17 | 三光株式会社 | Organophosphorus compound, epoxy resin composition and preparing method of organophosphorus compound |
| JP2015003875A (en) * | 2013-06-20 | 2015-01-08 | 三光株式会社 | Phosphorus compound and method for producing the same |
| JP2016003216A (en) * | 2014-06-18 | 2016-01-12 | 三光株式会社 | Phosphorus-containing epoxy compound, diastereomer mixture, and method for producing phosphorus-containing epoxy compound |
| JP2016020308A (en) * | 2014-07-11 | 2016-02-04 | 三光株式会社 | Method for producing cyclic phosphorus-containing epoxy compound |
| WO2018180267A1 (en) * | 2017-03-29 | 2018-10-04 | 新日鉄住金化学株式会社 | Phosphorus-containing phenolic compound, phosphorus-containing epoxy resin, curable resin composition thereof, or epoxy resin composition and cured product thereof |
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| US4116936A (en) | 1975-07-23 | 1978-09-26 | The Dow Chemical Company | Polyvinylbenzyl ethers of polyphenols, their polymers and copolymers |
| JP4351466B2 (en) * | 2003-05-02 | 2009-10-28 | 東都化成株式会社 | Phosphorus-containing vinyl benzyl ether compound and flame retardant resin composition containing the compound as an essential component |
| CN106366128B (en) * | 2015-07-24 | 2019-05-07 | 中山台光电子材料有限公司 | Phosphine phenanthrene class compound and its preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104211732A (en) * | 2013-05-31 | 2014-12-17 | 三光株式会社 | Organophosphorus compound, epoxy resin composition and preparing method of organophosphorus compound |
| JP2015003875A (en) * | 2013-06-20 | 2015-01-08 | 三光株式会社 | Phosphorus compound and method for producing the same |
| JP2016003216A (en) * | 2014-06-18 | 2016-01-12 | 三光株式会社 | Phosphorus-containing epoxy compound, diastereomer mixture, and method for producing phosphorus-containing epoxy compound |
| JP2016020308A (en) * | 2014-07-11 | 2016-02-04 | 三光株式会社 | Method for producing cyclic phosphorus-containing epoxy compound |
| WO2018180267A1 (en) * | 2017-03-29 | 2018-10-04 | 新日鉄住金化学株式会社 | Phosphorus-containing phenolic compound, phosphorus-containing epoxy resin, curable resin composition thereof, or epoxy resin composition and cured product thereof |
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| JP7239357B2 (en) | 2023-03-14 |
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| KR20200110204A (en) | 2020-09-23 |
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