WO2014006828A1 - Novel diphosphonium salt and method for producing same - Google Patents
Novel diphosphonium salt and method for producing same Download PDFInfo
- Publication number
- WO2014006828A1 WO2014006828A1 PCT/JP2013/003774 JP2013003774W WO2014006828A1 WO 2014006828 A1 WO2014006828 A1 WO 2014006828A1 JP 2013003774 W JP2013003774 W JP 2013003774W WO 2014006828 A1 WO2014006828 A1 WO 2014006828A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bis
- phosphonium
- hydroxyphenyl
- biphenyl
- benzene
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 239000002216 antistatic agent Substances 0.000 claims abstract description 11
- -1 hydroxyphenyl halide Chemical class 0.000 claims description 323
- 238000006243 chemical reaction Methods 0.000 claims description 56
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000002816 nickel compounds Chemical class 0.000 claims description 8
- 150000002900 organolithium compounds Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229920005989 resin Polymers 0.000 abstract description 18
- 239000011347 resin Substances 0.000 abstract description 18
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 abstract description 8
- 229920005668 polycarbonate resin Polymers 0.000 abstract description 7
- 239000004431 polycarbonate resin Substances 0.000 abstract description 7
- 239000003822 epoxy resin Substances 0.000 abstract description 6
- 229920000647 polyepoxide Polymers 0.000 abstract description 6
- 229920001187 thermosetting polymer Polymers 0.000 abstract 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 abstract description 2
- 150000001768 cations Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 description 440
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 215
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 207
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical group FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 85
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 19
- 150000001649 bromium compounds Chemical group 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 150000004694 iodide salts Chemical group 0.000 description 13
- OELITJOIJNBCNA-UHFFFAOYSA-N OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 OELITJOIJNBCNA-UHFFFAOYSA-N 0.000 description 12
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- QOPABJOZVXZFJG-UHFFFAOYSA-N 4-diphenylphosphanylphenol Chemical compound C1=CC(O)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QOPABJOZVXZFJG-UHFFFAOYSA-N 0.000 description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- KTQDYGVEEFGIIL-UHFFFAOYSA-N n-fluorosulfonylsulfamoyl fluoride Chemical group FS(=O)(=O)NS(F)(=O)=O KTQDYGVEEFGIIL-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 150000001805 chlorine compounds Chemical group 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 150000003949 imides Chemical class 0.000 description 7
- 239000011342 resin composition Substances 0.000 description 7
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 7
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 6
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- JSCQRBFJHDBAEJ-UHFFFAOYSA-N CC1=CC(P(C(C=C2)=CC=C2O)C2=CC=CC(C)=C2)=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC1=CC(P(C(C=C2)=CC=C2O)C2=CC=CC(C)=C2)=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 JSCQRBFJHDBAEJ-UHFFFAOYSA-N 0.000 description 6
- ZRWJXRVUISEFEG-UHFFFAOYSA-N CC1=CC(P(C(C=C2)=CC=C2O)C2=CC=CC(C)=C2)=CC=C1.C1=CC=CC=C1 Chemical compound CC1=CC(P(C(C=C2)=CC=C2O)C2=CC=CC(C)=C2)=CC=C1.C1=CC=CC=C1 ZRWJXRVUISEFEG-UHFFFAOYSA-N 0.000 description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- CEUWWRFKARIADH-UHFFFAOYSA-N 1,1'-biphenyl;diphenylphosphane Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1PC1=CC=CC=C1 CEUWWRFKARIADH-UHFFFAOYSA-N 0.000 description 5
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- AIQUXOAZIJCFRR-UHFFFAOYSA-N OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=C1 Chemical compound OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=CC=C1 AIQUXOAZIJCFRR-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical group CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 4
- 239000004210 ether based solvent Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 3
- PONNEDUAHHJLKG-UHFFFAOYSA-N CC(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)C)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CC(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)C)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 PONNEDUAHHJLKG-UHFFFAOYSA-N 0.000 description 3
- HQWQOEMBSPSFDW-UHFFFAOYSA-N CCC(C=C1)=CC=C1P(C1=CC=C(CC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CCC(C=C1)=CC=C1P(C1=CC=C(CC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 HQWQOEMBSPSFDW-UHFFFAOYSA-N 0.000 description 3
- OGAJKSXDXWJYAE-UHFFFAOYSA-N COC(C=C1)=CC=C1P(C(C=C1)=CC=C1O)C(C=C1)=CC=C1OC.C1=CC=CC=C1 Chemical compound COC(C=C1)=CC=C1P(C(C=C1)=CC=C1O)C(C=C1)=CC=C1OC.C1=CC=CC=C1 OGAJKSXDXWJYAE-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OUNGYKFQJPYBHY-UHFFFAOYSA-N OC(C=C1)=CC=C1P(C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12)C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12.C1=CC=CC=C1 Chemical compound OC(C=C1)=CC=C1P(C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12)C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12.C1=CC=CC=C1 OUNGYKFQJPYBHY-UHFFFAOYSA-N 0.000 description 3
- SVUYFKZSBXCDIA-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 SVUYFKZSBXCDIA-UHFFFAOYSA-N 0.000 description 3
- USCYNGNWPLFZCJ-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=CC=C1)C1=CC=CC=C1 USCYNGNWPLFZCJ-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IYDSCYOEWRQDIQ-UHFFFAOYSA-N (3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P)=C1 IYDSCYOEWRQDIQ-UHFFFAOYSA-N 0.000 description 2
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYBOYRLZHPAJAY-UHFFFAOYSA-N C1=CC=CC=C1.OC1=CC=C(C=C1)P(C1=C(C(=C(C=C1)C)C)C)C1=C(C(=C(C=C1)C)C)C Chemical compound C1=CC=CC=C1.OC1=CC=C(C=C1)P(C1=C(C(=C(C=C1)C)C)C)C1=C(C(=C(C=C1)C)C)C VYBOYRLZHPAJAY-UHFFFAOYSA-N 0.000 description 2
- KWDRPPNTIYJOIU-UHFFFAOYSA-N CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=C1)=CC=C1P(C1=CC=C(C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 KWDRPPNTIYJOIU-UHFFFAOYSA-N 0.000 description 2
- NWWDRFNFOSKOGD-UHFFFAOYSA-N CC(C=C1)=CC=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=C1)=CC=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 NWWDRFNFOSKOGD-UHFFFAOYSA-N 0.000 description 2
- UJLWAFOICFCOIG-UHFFFAOYSA-N CC(C=C1C)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C=C1C.C1=CC=CC=C1 Chemical compound CC(C=C1C)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C=C1C.C1=CC=CC=C1 UJLWAFOICFCOIG-UHFFFAOYSA-N 0.000 description 2
- GLUNWNIOXSMZKF-UHFFFAOYSA-N CC(C=CC=C1)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=CC=C1)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 GLUNWNIOXSMZKF-UHFFFAOYSA-N 0.000 description 2
- DBTWHOSWSKHEBU-UHFFFAOYSA-N CC(C=CC=C1)=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CC(C=CC=C1)=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 DBTWHOSWSKHEBU-UHFFFAOYSA-N 0.000 description 2
- LZCNRHCPKTZXLQ-UHFFFAOYSA-N CC1=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=C(C)C(C)=C2)=C(C)C(C)=C1C.C1=CC=CC=C1 Chemical compound CC1=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=C(C)C(C)=C2)=C(C)C(C)=C1C.C1=CC=CC=C1 LZCNRHCPKTZXLQ-UHFFFAOYSA-N 0.000 description 2
- SFKVCPIQDFAPGY-UHFFFAOYSA-N CC1=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2)=C(C)C(C)=C1.C1=CC=CC=C1 Chemical compound CC1=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2)=C(C)C(C)=C1.C1=CC=CC=C1 SFKVCPIQDFAPGY-UHFFFAOYSA-N 0.000 description 2
- PBAXWUDTEYNXHA-UHFFFAOYSA-N CCCCC(C=C1)=CC=C1P(C1=CC=C(CCCC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CCCCC(C=C1)=CC=C1P(C1=CC=C(CCCC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 PBAXWUDTEYNXHA-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- 229910013063 LiBF 4 Inorganic materials 0.000 description 2
- 229910013870 LiPF 6 Inorganic materials 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- VCHJLGIRAWRQMG-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=C(C=CC=C1)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=C(C=CC=C1)C VCHJLGIRAWRQMG-UHFFFAOYSA-N 0.000 description 2
- CYEJSCXSTVGMKV-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C=1C=C(C=CC1)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C=1C=C(C=CC1)C CYEJSCXSTVGMKV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002500 ions Chemical group 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-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
- HUCQPHINKBNKRU-UHFFFAOYSA-N (4-methylphenyl)phosphane Chemical compound CC1=CC=C(P)C=C1 HUCQPHINKBNKRU-UHFFFAOYSA-N 0.000 description 1
- ZFDVOTAFEZKEBC-UHFFFAOYSA-N 1,1'-biphenyl bis(2-methylphenyl)phosphane Chemical group C1(=C(C=CC=C1)PC1=C(C=CC=C1)C)C.C1(=CC=CC=C1)C1=CC=CC=C1 ZFDVOTAFEZKEBC-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
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- QUVNEIJTQUASHZ-UHFFFAOYSA-N 1-(4-bromophenyl)-4-chloro-2-phenylbenzene Chemical group BrC1=CC=C(C=C1)C=1C(=CC(=CC=1)Cl)C1=CC=CC=C1 QUVNEIJTQUASHZ-UHFFFAOYSA-N 0.000 description 1
- LILVGURUYVZWHY-UHFFFAOYSA-N 1-(4-bromophenyl)-4-iodo-2-phenylbenzene Chemical group BrC1=CC=C(C=C1)C=1C(=CC(=CC=1)I)C1=CC=CC=C1 LILVGURUYVZWHY-UHFFFAOYSA-N 0.000 description 1
- WMXVUHANYJZYHO-UHFFFAOYSA-N 1-bromo-4-(4-chlorophenyl)benzene Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Br)C=C1 WMXVUHANYJZYHO-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- HCHAMYGZDLHKMD-UHFFFAOYSA-N 1-chloro-4-(4-iodophenyl)benzene Chemical group C1=CC(Cl)=CC=C1C1=CC=C(I)C=C1 HCHAMYGZDLHKMD-UHFFFAOYSA-N 0.000 description 1
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 1
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- WEZHMYSASZECSI-UHFFFAOYSA-N 1-iodo-4-(4-phenylphenyl)benzene Chemical compound C1=CC(I)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 WEZHMYSASZECSI-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- XYUINKARGUCCQJ-UHFFFAOYSA-N 3-imino-n-propylpropan-1-amine Chemical compound CCCNCCC=N XYUINKARGUCCQJ-UHFFFAOYSA-N 0.000 description 1
- RXXCIBALSKQCAE-UHFFFAOYSA-N 3-methylbutoxymethylbenzene Chemical compound CC(C)CCOCC1=CC=CC=C1 RXXCIBALSKQCAE-UHFFFAOYSA-N 0.000 description 1
- YTBRNEUEFCNVHC-UHFFFAOYSA-N 4,4'-dichlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1 YTBRNEUEFCNVHC-UHFFFAOYSA-N 0.000 description 1
- YYEPIZCWZXJNOY-UHFFFAOYSA-N 4-[(4-methylphenyl)-phenylphosphanyl]phenol Chemical compound CC1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=C(C=C3)O YYEPIZCWZXJNOY-UHFFFAOYSA-N 0.000 description 1
- PSGOBEGWIPRUKB-UHFFFAOYSA-N 4-bromo-1-(4-bromophenyl)-2-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1C1=CC=CC=C1 PSGOBEGWIPRUKB-UHFFFAOYSA-N 0.000 description 1
- RGYCQGZWQZPGME-UHFFFAOYSA-N 4-chloro-1-(4-chlorophenyl)-2-phenylbenzene Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1C1=CC=CC=C1 RGYCQGZWQZPGME-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- QEHKLAKKWSWERC-UHFFFAOYSA-N BrC1=CC=C(C=C1)C1=CC=C(C=C1)I.BrC1=CC=C(C=C1)C1=CC=C(C=C1)Br Chemical group BrC1=CC=C(C=C1)C1=CC=C(C=C1)I.BrC1=CC=C(C=C1)C1=CC=C(C=C1)Br QEHKLAKKWSWERC-UHFFFAOYSA-N 0.000 description 1
- IIGCVMJFGBJCGL-UHFFFAOYSA-N BrP(C1=C(C=CC=C1)C)C1=CC=CC=C1 Chemical compound BrP(C1=C(C=CC=C1)C)C1=CC=CC=C1 IIGCVMJFGBJCGL-UHFFFAOYSA-N 0.000 description 1
- CXZXDMUMEKMJRO-UHFFFAOYSA-N C1(=CC(=CC=C1)P(Br)C=1C=C(C=CC=1)C)C Chemical compound C1(=CC(=CC=C1)P(Br)C=1C=C(C=CC=1)C)C CXZXDMUMEKMJRO-UHFFFAOYSA-N 0.000 description 1
- RQLKWZSQWKCHCC-UHFFFAOYSA-N C1(=CC(=CC=C1)P(I)C=1C=C(C=CC1)C)C Chemical compound C1(=CC(=CC=C1)P(I)C=1C=C(C=CC1)C)C RQLKWZSQWKCHCC-UHFFFAOYSA-N 0.000 description 1
- GACOOIPTZHFNSM-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=C(C=CC=C1)C)I Chemical compound C1(=CC=CC=C1)P(C1=C(C=CC=C1)C)I GACOOIPTZHFNSM-UHFFFAOYSA-N 0.000 description 1
- OHCPCPIELRQSTI-UHFFFAOYSA-N C1(=CC=CC=C1)P(C1=CC=C(C=C1)C)Br Chemical compound C1(=CC=CC=C1)P(C1=CC=C(C=C1)C)Br OHCPCPIELRQSTI-UHFFFAOYSA-N 0.000 description 1
- GGLPGMIIICCSDU-UHFFFAOYSA-N C1(=CC=CC=C1)P(C=1C=C(C=CC1)C)Br Chemical compound C1(=CC=CC=C1)P(C=1C=C(C=CC1)C)Br GGLPGMIIICCSDU-UHFFFAOYSA-N 0.000 description 1
- NLZRNKAXTBTGME-UHFFFAOYSA-N C1=CC=C(C=C1)C1=CC=CC=C1.C1(=CC=C(C=C1)PC1=CC=C(C=C1)C)C Chemical group C1=CC=C(C=C1)C1=CC=CC=C1.C1(=CC=C(C=C1)PC1=CC=C(C=C1)C)C NLZRNKAXTBTGME-UHFFFAOYSA-N 0.000 description 1
- IOZOIAUFVQVGHK-UHFFFAOYSA-N C1=CC=C(C=C1)C1=CC=CC=C1.C1(=CC=CC=C1)PC=1C=C(C=CC1)C Chemical group C1=CC=C(C=C1)C1=CC=CC=C1.C1(=CC=CC=C1)PC=1C=C(C=CC1)C IOZOIAUFVQVGHK-UHFFFAOYSA-N 0.000 description 1
- MGBYSPMEKQVSEZ-UHFFFAOYSA-N C1=CC=CC=C1.C1(=C(C=CC=C1)PC1=C(C=CC=C1)C)C Chemical compound C1=CC=CC=C1.C1(=C(C=CC=C1)PC1=C(C=CC=C1)C)C MGBYSPMEKQVSEZ-UHFFFAOYSA-N 0.000 description 1
- XSHKONKXOSLWPW-UHFFFAOYSA-N C1=CC=CC=C1.C1(=CC(=CC=C1)PC=1C=C(C=CC1)C)C Chemical compound C1=CC=CC=C1.C1(=CC(=CC=C1)PC=1C=C(C=CC1)C)C XSHKONKXOSLWPW-UHFFFAOYSA-N 0.000 description 1
- LQIUBKXISNZMBK-UHFFFAOYSA-N C1=CC=CC=C1.C1(=CC=C(C=C1)PC1=CC=C(C=C1)C)C Chemical compound C1=CC=CC=C1.C1(=CC=C(C=C1)PC1=CC=C(C=C1)C)C LQIUBKXISNZMBK-UHFFFAOYSA-N 0.000 description 1
- OXKMDILAHMZXIS-UHFFFAOYSA-N C1=CC=CC=C1.C1(=CC=CC=C1)PC1=C(C=CC=C1)C Chemical compound C1=CC=CC=C1.C1(=CC=CC=C1)PC1=C(C=CC=C1)C OXKMDILAHMZXIS-UHFFFAOYSA-N 0.000 description 1
- JSCGLQUGPOAPDJ-UHFFFAOYSA-N C1=CC=CC=C1.C1(=CC=CC=C1)PC1=CC=C(C=C1)C Chemical compound C1=CC=CC=C1.C1(=CC=CC=C1)PC1=CC=C(C=C1)C JSCGLQUGPOAPDJ-UHFFFAOYSA-N 0.000 description 1
- RNXCGVFODXNBKD-UHFFFAOYSA-N C1=CC=CC=C1.C1(=CC=CC=C1)PC=1C=C(C=CC1)C Chemical compound C1=CC=CC=C1.C1(=CC=CC=C1)PC=1C=C(C=CC1)C RNXCGVFODXNBKD-UHFFFAOYSA-N 0.000 description 1
- KBEXYQQXSQUERG-UHFFFAOYSA-N CC(C(C)=C1C)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C(C)=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C(C)=C1C)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C(C)=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 KBEXYQQXSQUERG-UHFFFAOYSA-N 0.000 description 1
- FVZAVDWSFWBWQZ-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C)(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 FVZAVDWSFWBWQZ-UHFFFAOYSA-N 0.000 description 1
- MHLRGNQTBSNVKV-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)(C)C)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CC(C)(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)(C)C)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 MHLRGNQTBSNVKV-UHFFFAOYSA-N 0.000 description 1
- DEKDCAGAXQWLPJ-UHFFFAOYSA-N CC(C)(C)CC(C=C1)=CC=C1P(C1=CC=C(CC(C)(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C)(C)CC(C=C1)=CC=C1P(C1=CC=C(CC(C)(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 DEKDCAGAXQWLPJ-UHFFFAOYSA-N 0.000 description 1
- UJKWMLIGWGVCKH-UHFFFAOYSA-N CC(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C)C(C=C1)=CC=C1P(C1=CC=C(C(C)C)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 UJKWMLIGWGVCKH-UHFFFAOYSA-N 0.000 description 1
- DJMRFJTWJFCXQK-UHFFFAOYSA-N CC(C=C1)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=C1)=C(C)C(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C(C)=C(C)C=C1.C(C=C1)=CC=C1C1=CC=CC=C1 DJMRFJTWJFCXQK-UHFFFAOYSA-N 0.000 description 1
- IZRWHNFYTJJJFX-UHFFFAOYSA-N CC(C=C1)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=C1)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1.C(C=C1)=CC=C1C1=CC=CC=C1 IZRWHNFYTJJJFX-UHFFFAOYSA-N 0.000 description 1
- KYDBWACIWOEMHV-UHFFFAOYSA-N CC(C=C1)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1.C1=CC=CC=C1 Chemical compound CC(C=C1)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1.C1=CC=CC=C1 KYDBWACIWOEMHV-UHFFFAOYSA-N 0.000 description 1
- LUZHAKXPJDFYED-UHFFFAOYSA-N CC(C=C1C)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=C1C)=CC(C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=C(C)C=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 LUZHAKXPJDFYED-UHFFFAOYSA-N 0.000 description 1
- UKSZAZOCRMDQNO-UHFFFAOYSA-N CC(C=CC=C1)=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=CC=C1)=C1P(C1=CC=CC=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 UKSZAZOCRMDQNO-UHFFFAOYSA-N 0.000 description 1
- RVTKJQHNAACFLM-UHFFFAOYSA-N CC(C=CC=C1C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=CC=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC(C=CC=C1C)=C1P(C(C=C1)=CC=C1O)C1=C(C)C=CC=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 RVTKJQHNAACFLM-UHFFFAOYSA-N 0.000 description 1
- VCKREVHCXDIBJY-UHFFFAOYSA-N CC1=C(C)C(C)=CC(P(C(C=C2)=CC=C2O)C2=CC(C)=C(C)C(C)=C2)=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC1=C(C)C(C)=CC(P(C(C=C2)=CC=C2O)C2=CC(C)=C(C)C(C)=C2)=C1.C(C=C1)=CC=C1C1=CC=CC=C1 VCKREVHCXDIBJY-UHFFFAOYSA-N 0.000 description 1
- UTNCXZRMWUZPNI-UHFFFAOYSA-N CC1=CC(C)=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2C)=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC1=CC(C)=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2C)=C1C.C(C=C1)=CC=C1C1=CC=CC=C1 UTNCXZRMWUZPNI-UHFFFAOYSA-N 0.000 description 1
- RCCRQFSCFBPFNQ-UHFFFAOYSA-N CC1=CC(C)=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2C)=C1C.C1=CC=CC=C1 Chemical compound CC1=CC(C)=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC(C)=C2C)=C1C.C1=CC=CC=C1 RCCRQFSCFBPFNQ-UHFFFAOYSA-N 0.000 description 1
- DHDQBYLAOWRCAL-UHFFFAOYSA-N CC1=CC(C)=CC(P(C(C=C2)=CC=C2O)C2=CC(C)=CC(C)=C2)=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CC1=CC(C)=CC(P(C(C=C2)=CC=C2O)C2=CC(C)=CC(C)=C2)=C1.C(C=C1)=CC=C1C1=CC=CC=C1 DHDQBYLAOWRCAL-UHFFFAOYSA-N 0.000 description 1
- XMLFDIQORDOWGI-UHFFFAOYSA-N CC1=CC=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC=C2C)=C1C.C1=CC=CC=C1 Chemical compound CC1=CC=C(C)C(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC=C2C)=C1C.C1=CC=CC=C1 XMLFDIQORDOWGI-UHFFFAOYSA-N 0.000 description 1
- ADTGGUIRRWONTC-UHFFFAOYSA-N CC1=CC=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC=C2)=C1C.C1=CC=CC=C1 Chemical compound CC1=CC=CC(P(C(C=C2)=CC=C2O)C2=C(C)C(C)=CC=C2)=C1C.C1=CC=CC=C1 ADTGGUIRRWONTC-UHFFFAOYSA-N 0.000 description 1
- KYQLTLCEPZWEJA-UHFFFAOYSA-N CCC(C=C1)=CC=C1P(C1=CC=C(CC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CCC(C=C1)=CC=C1P(C1=CC=C(CC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 KYQLTLCEPZWEJA-UHFFFAOYSA-N 0.000 description 1
- DCAVHDBVZVPRHO-UHFFFAOYSA-N CCCC(C=C1)=CC=C1P(C1=CC=C(CCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CCCC(C=C1)=CC=C1P(C1=CC=C(CCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 DCAVHDBVZVPRHO-UHFFFAOYSA-N 0.000 description 1
- ZKHLTEYVRWIIIU-UHFFFAOYSA-N CCCCC(C=C1)=CC=C1P(C1=CC=C(CCCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CCCCC(C=C1)=CC=C1P(C1=CC=C(CCCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 ZKHLTEYVRWIIIU-UHFFFAOYSA-N 0.000 description 1
- UGBBMBRTDBGSKZ-UHFFFAOYSA-N CCCCCCCCC(C=C1)=CC=C1P(C1=CC=C(CCCCCCCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group CCCCCCCCC(C=C1)=CC=C1P(C1=CC=C(CCCCCCCC)C=C1)C(C=C1)=CC=C1O.C(C=C1)=CC=C1C1=CC=CC=C1 UGBBMBRTDBGSKZ-UHFFFAOYSA-N 0.000 description 1
- ZORIOKXVQUJFBK-UHFFFAOYSA-N CCCCCCCCC(C=C1)=CC=C1P(C1=CC=C(CCCCCCCC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 Chemical compound CCCCCCCCC(C=C1)=CC=C1P(C1=CC=C(CCCCCCCC)C=C1)C(C=C1)=CC=C1O.C1=CC=CC=C1 ZORIOKXVQUJFBK-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910020808 NaBF Inorganic materials 0.000 description 1
- 229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
- BHKINWDPUYFACD-UHFFFAOYSA-N OC(C=C1)=CC=C1P(C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12)C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group OC(C=C1)=CC=C1P(C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12)C(C=C1)=CC=C1C1=CC=CC2=CC=CC=C12.C(C=C1)=CC=C1C1=CC=CC=C1 BHKINWDPUYFACD-UHFFFAOYSA-N 0.000 description 1
- JXQMAMXNZXDGJT-UHFFFAOYSA-N OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 Chemical group OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.OC(C=C1)=CC=C1P(C1=CC=CC=C1)C1=CC=CC=C1.C(C=C1)=CC=C1C1=CC=CC=C1 JXQMAMXNZXDGJT-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NLTIGRVYKSWYKZ-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 NLTIGRVYKSWYKZ-UHFFFAOYSA-N 0.000 description 1
- SCCRRTFGLAROMM-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 SCCRRTFGLAROMM-UHFFFAOYSA-N 0.000 description 1
- DELILRLIPOSAJT-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C DELILRLIPOSAJT-UHFFFAOYSA-N 0.000 description 1
- TVJLAERUCGCZMI-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 TVJLAERUCGCZMI-UHFFFAOYSA-N 0.000 description 1
- FUCOQNPGORAYDG-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC FUCOQNPGORAYDG-UHFFFAOYSA-N 0.000 description 1
- VUPKWHPHRNMCTR-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC VUPKWHPHRNMCTR-UHFFFAOYSA-N 0.000 description 1
- GONKMSCJDIYEFT-UHFFFAOYSA-N [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 Chemical compound [Br-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 GONKMSCJDIYEFT-UHFFFAOYSA-N 0.000 description 1
- PFZTYZGWJQUXJD-UHFFFAOYSA-N [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC=C1)C)C)C1=C(C(=CC=C1)C)C Chemical compound [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC=C1)C)C)C1=C(C(=CC=C1)C)C PFZTYZGWJQUXJD-UHFFFAOYSA-N 0.000 description 1
- WXSCSMDIDXNHSZ-UHFFFAOYSA-N [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C Chemical compound [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C WXSCSMDIDXNHSZ-UHFFFAOYSA-N 0.000 description 1
- OONZRUNEEPSHIP-UHFFFAOYSA-N [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C Chemical compound [Br-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C OONZRUNEEPSHIP-UHFFFAOYSA-N 0.000 description 1
- DSSIVHWAQPTHCB-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 DSSIVHWAQPTHCB-UHFFFAOYSA-N 0.000 description 1
- CTHXODKGLSVJBF-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 CTHXODKGLSVJBF-UHFFFAOYSA-N 0.000 description 1
- OAAACXKBJGOCAN-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C OAAACXKBJGOCAN-UHFFFAOYSA-N 0.000 description 1
- HDHQNQKWDJEUBG-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 HDHQNQKWDJEUBG-UHFFFAOYSA-N 0.000 description 1
- NXTVGCAEIWJNIR-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC NXTVGCAEIWJNIR-UHFFFAOYSA-N 0.000 description 1
- GNCHCNPQGAIVKZ-UHFFFAOYSA-N [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 GNCHCNPQGAIVKZ-UHFFFAOYSA-N 0.000 description 1
- ABFVSMQRJCHDNH-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=C(C=C1)C)C)C)C1=C(C(=C(C=C1)C)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=C(C=C1)C)C)C)C1=C(C(=C(C=C1)C)C)C ABFVSMQRJCHDNH-UHFFFAOYSA-N 0.000 description 1
- LNSVFQQONTYTMX-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC=C1)C)C)C1=C(C(=CC=C1)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC=C1)C)C)C1=C(C(=CC=C1)C)C LNSVFQQONTYTMX-UHFFFAOYSA-N 0.000 description 1
- MDWCTKZKWOZKLG-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C MDWCTKZKWOZKLG-UHFFFAOYSA-N 0.000 description 1
- XUJLFVRVMIDQPM-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC(=C1)C)C)C1=C(C=CC(=C1)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC(=C1)C)C)C1=C(C=CC(=C1)C)C XUJLFVRVMIDQPM-UHFFFAOYSA-N 0.000 description 1
- ORRXNMRJZAZAMW-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1C)C)C1=C(C=CC=C1C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1C)C)C1=C(C=CC=C1C)C ORRXNMRJZAZAMW-UHFFFAOYSA-N 0.000 description 1
- MBHYQHKEIORLFJ-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=C(C=C1)C)C)C1=CC(=C(C=C1)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=C(C=C1)C)C)C1=CC(=C(C=C1)C)C MBHYQHKEIORLFJ-UHFFFAOYSA-N 0.000 description 1
- DWUILZUDOKURMR-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C)C)C1=CC(=CC(=C1)C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C)C)C1=CC(=CC(=C1)C)C DWUILZUDOKURMR-UHFFFAOYSA-N 0.000 description 1
- VBPGVBIYBNMHIB-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 VBPGVBIYBNMHIB-UHFFFAOYSA-N 0.000 description 1
- SMODNFHCEKFZRM-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C SMODNFHCEKFZRM-UHFFFAOYSA-N 0.000 description 1
- DUFDUMNDMAASRL-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C DUFDUMNDMAASRL-UHFFFAOYSA-N 0.000 description 1
- DFMPGOCIIORUQQ-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=CC=C1 Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=CC=C1 DFMPGOCIIORUQQ-UHFFFAOYSA-N 0.000 description 1
- CNAUYZHSQMMZPK-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=CC2=CC=CC=C12 CNAUYZHSQMMZPK-UHFFFAOYSA-N 0.000 description 1
- KMYGNDMTSTXKAD-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CC(C)(C)C)C1=CC=C(C=C1)CC(C)(C)C Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CC(C)(C)C)C1=CC=C(C=C1)CC(C)(C)C KMYGNDMTSTXKAD-UHFFFAOYSA-N 0.000 description 1
- ONQHDYVEOCZORP-UHFFFAOYSA-N [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCC)C1=CC=C(C=C1)CCC Chemical compound [Cl-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCC)C1=CC=C(C=C1)CCC ONQHDYVEOCZORP-UHFFFAOYSA-N 0.000 description 1
- ROWVUTMUSJAABC-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC(=C1)C)C)C1=C(C=CC(=C1)C)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC(=C1)C)C)C1=C(C=CC(=C1)C)C ROWVUTMUSJAABC-UHFFFAOYSA-N 0.000 description 1
- KTVXTMYVBQLDSA-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1)C)C1=CC=CC=C1 KTVXTMYVBQLDSA-UHFFFAOYSA-N 0.000 description 1
- RADDZKHTRMPWSB-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1C)C)C1=C(C=CC=C1C)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C=CC=C1C)C)C1=C(C=CC=C1C)C RADDZKHTRMPWSB-UHFFFAOYSA-N 0.000 description 1
- GOUJAVPYKWILLP-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=C(C=C1)C)C)C1=CC(=C(C=C1)C)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=C(C=C1)C)C)C1=CC(=C(C=C1)C)C GOUJAVPYKWILLP-UHFFFAOYSA-N 0.000 description 1
- JVGICMFPVNVLMX-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C JVGICMFPVNVLMX-UHFFFAOYSA-N 0.000 description 1
- TVSQXAHCCBNTTD-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C(C)C)C1=CC=C(C=C1)C(C)C TVSQXAHCCBNTTD-UHFFFAOYSA-N 0.000 description 1
- MAUPSERNBAUPJN-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)C)C1=CC=C(C=C1)C MAUPSERNBAUPJN-UHFFFAOYSA-N 0.000 description 1
- LNPRFUSNOZVCDZ-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCC)C1=CC=C(C=C1)CCCC LNPRFUSNOZVCDZ-UHFFFAOYSA-N 0.000 description 1
- JIGGZFSHRYWIIN-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC JIGGZFSHRYWIIN-UHFFFAOYSA-N 0.000 description 1
- ZRMXIOJJRIAERD-UHFFFAOYSA-N [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 Chemical compound [I-].C1=CC=C(C=C1)C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C1=CC=CC=C1 ZRMXIOJJRIAERD-UHFFFAOYSA-N 0.000 description 1
- RJXFCUBCCZXPEV-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=C(C=C1C)C)C)C)C1=C(C(=C(C=C1C)C)C)C Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=C(C=C1C)C)C)C)C1=C(C(=C(C=C1C)C)C)C RJXFCUBCCZXPEV-UHFFFAOYSA-N 0.000 description 1
- MAEGVPXJNBQKCM-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC(=C1C)C)C)C)C1=C(C(=CC(=C1C)C)C)C Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=C(C(=CC(=C1C)C)C)C)C1=C(C(=CC(=C1C)C)C)C MAEGVPXJNBQKCM-UHFFFAOYSA-N 0.000 description 1
- ZAUODLSHTJCFTI-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1 ZAUODLSHTJCFTI-UHFFFAOYSA-N 0.000 description 1
- IDTZEIILHRADDV-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCC)C1=CC=C(C=C1)CCC Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCC)C1=CC=C(C=C1)CCC IDTZEIILHRADDV-UHFFFAOYSA-N 0.000 description 1
- RXYDGCOWPVVMFA-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCC)C1=CC=C(C=C1)CCCCC RXYDGCOWPVVMFA-UHFFFAOYSA-N 0.000 description 1
- BBBQYPPFUMFPRM-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCCC)C1=CC=C(C=C1)CCCCCC Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)CCCCCC)C1=CC=C(C=C1)CCCCCC BBBQYPPFUMFPRM-UHFFFAOYSA-N 0.000 description 1
- OQJDESMPUDHZQF-UHFFFAOYSA-N [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C=1C=C(C=CC1)C Chemical compound [I-].C1=CC=CC=C1.OC1=CC=C(C=C1)[PH+](C=1C=C(C=CC1)C)C=1C=C(C=CC1)C OQJDESMPUDHZQF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- ZUENHQDDMWOOQE-UHFFFAOYSA-N benzene;diphenylphosphane Chemical compound C1=CC=CC=C1.C=1C=CC=CC=1PC1=CC=CC=C1 ZUENHQDDMWOOQE-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- RZSMSXXOYMFIKN-UHFFFAOYSA-N bromo(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(Br)C1=CC=CC=C1 RZSMSXXOYMFIKN-UHFFFAOYSA-N 0.000 description 1
- NBRSVRBGWFULSG-UHFFFAOYSA-N bromo-bis(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(Br)C1=CC=CC=C1C NBRSVRBGWFULSG-UHFFFAOYSA-N 0.000 description 1
- KQCBLYDIRGVDSR-UHFFFAOYSA-N bromo-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(Br)C1=CC=C(C)C=C1 KQCBLYDIRGVDSR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZSTLQYDNYDFAOQ-UHFFFAOYSA-N chloro-(2-methylphenyl)-phenylphosphane Chemical compound CC1=CC=CC=C1P(Cl)C1=CC=CC=C1 ZSTLQYDNYDFAOQ-UHFFFAOYSA-N 0.000 description 1
- ZBZUIQWELHLBNE-UHFFFAOYSA-N chloro-(3-methylphenyl)-phenylphosphane Chemical compound CC1=CC=CC(P(Cl)C=2C=CC=CC=2)=C1 ZBZUIQWELHLBNE-UHFFFAOYSA-N 0.000 description 1
- ZCABTUOKUWHGRJ-UHFFFAOYSA-N chloro-(4-methylphenyl)-phenylphosphane Chemical compound C1=CC(C)=CC=C1P(Cl)C1=CC=CC=C1 ZCABTUOKUWHGRJ-UHFFFAOYSA-N 0.000 description 1
- KAAGXBGJRWFWPT-UHFFFAOYSA-N chloro-bis(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(Cl)C1=CC=CC=C1C KAAGXBGJRWFWPT-UHFFFAOYSA-N 0.000 description 1
- QBCUUCZOCXEZSH-UHFFFAOYSA-N chloro-bis(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(Cl)C=2C=C(C)C=CC=2)=C1 QBCUUCZOCXEZSH-UHFFFAOYSA-N 0.000 description 1
- BJBXRRHIBSXGLF-UHFFFAOYSA-N chloro-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(Cl)C1=CC=C(C)C=C1 BJBXRRHIBSXGLF-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- QCYZGYHHITWIFQ-UHFFFAOYSA-N iodo(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(I)C1=CC=CC=C1 QCYZGYHHITWIFQ-UHFFFAOYSA-N 0.000 description 1
- XXAXFIBHVQAXNF-UHFFFAOYSA-N iodo-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(I)C1=CC=C(C)C=C1 XXAXFIBHVQAXNF-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- QAXHWUAAPKHMGA-UHFFFAOYSA-N iodophosphane Chemical compound IP QAXHWUAAPKHMGA-UHFFFAOYSA-N 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- YNXURHRFIMQACJ-UHFFFAOYSA-N lithium;methanidylbenzene Chemical compound [Li+].[CH2-]C1=CC=CC=C1 YNXURHRFIMQACJ-UHFFFAOYSA-N 0.000 description 1
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
- BFSQJYRFLQUZKX-UHFFFAOYSA-L nickel(ii) iodide Chemical compound I[Ni]I BFSQJYRFLQUZKX-UHFFFAOYSA-L 0.000 description 1
- NSVFPFUROXFZJS-UHFFFAOYSA-N nickel;hexahydrate Chemical compound O.O.O.O.O.O.[Ni] NSVFPFUROXFZJS-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5449—Polyphosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/50—Phosphorus bound to carbon only
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
Definitions
- the present invention relates to a novel diphosphonium salt, a production method thereof, and an antistatic agent and a curing accelerator containing the diphosphonium salt.
- tetraphenylphosphonium bistrifluoromethanesulfonylimide
- resin antistatic agent see Patent Document 1
- tetraphenylphosphonium bromide is known as a curing accelerator (curing catalyst) for thermosetting resins such as epoxy resins (see Patent Document 2).
- the present invention provides a novel diphosphonium salt that can impart excellent antistatic performance to a resin and is an excellent curing accelerator for a thermosetting resin, a method for producing the same, and a charge containing the diphosphonium salt
- the present invention relates to an inhibitor and a curing accelerator.
- the present inventors diligently studied to solve the above problems. As a result, it was found that the diphosphonium salts represented by the formulas (1) and (3) can impart excellent antistatic performance to the resin. Further, the inventors have found that the diphosphonium salt can be used as an excellent curing accelerator for thermosetting resins, and have completed the present invention.
- R 1 and R 2 may be the same or different from each other, and each represents an aryl group which may have a substituent.
- Y represents the formula (2):
- diphosphonium salt (1) Diphosphonium salt (hereinafter referred to as diphosphonium salt (1)), formula (3):
- the present invention relates to a method, and an antistatic agent and a curing accelerator containing the diphosphonium salt.
- the diphosphonium salts (1) and (3) of the present invention can impart excellent antistatic properties to the resin. Further, they are useful compounds because they can be used as excellent curing accelerators for thermosetting resins.
- R 1 and R 2 may be the same as or different from each other, and each represents an aryl group that may have a substituent.
- the aryl group which may have a substituent for example, phenyl group, 2-tolyl group, 3-tolyl group, 4-tolyl group, 2,3-xylyl group, 2,4-xylyl group, 2,5 -Xylyl group, 2,6-xylyl group, 3,4-xylyl group, 3,5-xylyl group, 2,3,4-trimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6 -Trimethylphenyl group, 2,4,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,3,4,5-tetramethylphenyl group, 2,3,4,6-tetramethylphenyl group 2,3,5,6-tetramethylphenyl group, pentamethylphenyl group, ethylphenyl group, n-propylphenyl group, pent
- n is an integer of 1 to 3
- the arylene group include a phenylene group, a biphenyl group, and a terphenyl group. Among them, a biphenyl group is preferable.
- a ⁇ represents BF 4 ⁇ , PF 6 ⁇ , (FSO 2 ) 2 N — or (CF 3 SO 2 ) 2 N — . Among them (CF 3 SO 2) 2 N - is preferred.
- X ⁇ represents a halogen ion.
- the halogen ion include chlorine ion, bromine ion and iodine ion. Among them, chlorine ion or bromine ion is preferable.
- 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl chloride 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (2- Tolyl) phosphonium ⁇ -4,4′-terphenyl chloride, 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium ⁇ -4,4′- Terphenyl chloride, 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium ⁇ -4,4′-terphenyl chloride, 1,1′- Bis ⁇ P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium ⁇ -4,4'-terphenyl chloride, 1,1'-bis ⁇ P- (4-hydroxy Phenyl) -P, P'-
- 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl iodide 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (2- Tolyl) phosphonium ⁇ -4,4′-terphenyl iodide, 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium ⁇ -4,4′- Terphenyl iodide, 1,1′-bis ⁇ P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium ⁇ -4,4′-terphenyl iodide, 1,1′- Bis ⁇ P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium ⁇ -4,4'-terphenyl iodide, 1,1'-bis ⁇ P-
- the diphosphonium salt (3) of the present invention can be produced by the following two steps. First, in the presence of an organolithium compound, the formula (4):
- X represents a halogen atom
- halodiarylphosphine hereinafter referred to as halodiarylphosphine (4)
- diphosphine (6) (Wherein R 1 , R 2 and Y are the same as above) (hereinafter referred to as diphosphine (6)) is obtained (hereinafter referred to as the first reaction step).
- diphosphine (6) obtained in the first reaction step is converted to formula (7) in the presence of a nickel compound:
- the diphosphonium salt (1) of the present invention is obtained by converting the diphosphonium salt (3) into the formula (8): M + ⁇ A ⁇ (8) (In the formula, M + represents a hydrogen ion or an alkali metal ion. A ⁇ is the same as above.) (Hereinafter, referred to as a compound (8)). Called the reaction step).
- the first reaction step is a step of producing diphosphine (6) by reacting halodiarylphosphine (4) and aryl dihalide (5) in the presence of an organolithium compound.
- halodiarylphosphine (4) used in the first reaction step include diphenylchlorophosphine, di (2-tolyl) chlorophosphine, di (3-tolyl) chlorophosphine, di (4-tolyl) chlorophosphine, P-phenyl-P- (2-tolyl) chlorophosphine, P-phenyl-P- (3-tolyl) chlorophosphine, P-phenyl-P- (4-tolyl) chlorophosphine, diphenylbromophosphine, di (2- Tolyl) bromophosphine, di (3-tolyl) bromophosphine, di (4-tolyl) bromophosphine, P-phenyl-P- (2-tolyl) bromophosphine, P-phenyl-P- (3-tolyl) bromophosphine , P-phenyl-P- (4-tolyl) bromine, P
- organic lithium compound used in the first reaction step examples include methyl lithium, ethyl lithium, isopropyl lithium, n-butyl lithium, sec-butyl lithium, phenyl lithium, benzyl lithium and the like. Of these, n-butyllithium is preferred.
- the amount of the organolithium compound used is usually 2 to 10 mol, preferably 3 to 7 mol, more preferably 4 to 5 mol, per 1 mol of the aryl dihalide (5).
- aryl dihalide (5) used in the first reaction step examples include 1,4-dichlorobenzene, 1-bromo-4-chlorobenzene, 1-chloro-4-iodobenzene, 1,4-dibromobenzene, 1 -Bromo-4-iodobenzene, 1,4-diiodobenzene, 4,4'-dichlorobiphenyl, 4-bromo-4'-chlorobiphenyl, 4-chloro-4'-iodobiphenyl, 4,4'-dibromobiphenyl 4-bromo-4′-iodobiphenyl, 4,4′-diiodobiphenyl, 4,4′-dichloroterphenyl, 4-bromo-4′-chloroterphenyl, 4-chloro-4′-iodotephenyl, Examples include 4,4′-dibromoterphenyl, 4-bromo-4′-iodoterphenyl, 4-
- the amount of the aryl dihalide (5) to be used is generally 0.2 to 0.5 mol, preferably 0.3 to 0.5 mol, more preferably 0.00 mol, per 1 mol of the halodiarylphosphine (4). 4 to 0.5 mol.
- the first reaction step is usually performed in a solvent.
- the solvent to be used is not particularly limited as long as it does not affect the reaction, and usually an aliphatic solvent such as pentane, hexane, heptane, and octane, and an aromatic solvent such as benzene, toluene, xylene, trimethylbenzene, and ethylbenzene.
- Ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane.
- ether solvents are preferable, and tetrahydrofuran is particularly preferable.
- the amount of the solvent used is usually 3 parts by weight or more, preferably 3 to 10 parts by weight, more preferably 6 to 8 parts by weight with respect to 1 part by weight of the aryl dihalide (5).
- the reaction in the first reaction step is usually performed by adding an organolithium compound to a mixed solution in which an aryl dihalide (5) and a solvent are mixed, and further adding a halodiarylphosphine (4).
- the temperature during the reaction between the aryl dihalide (5) and the organolithium compound is usually ⁇ 90 to ⁇ 40 ° C., preferably ⁇ 80 to ⁇ 60 ° C., more preferably ⁇ 80 to ⁇ 70 ° C.
- the reaction temperature of the reaction product of aryl dihalide (5) and organolithium compound with halodiarylphosphine (4) is usually ⁇ 90 ° C. to ⁇ 40 ° C., preferably ⁇ 80 to ⁇ 60 ° C. More preferably, it is ⁇ 80 ° C. to ⁇ 70 ° C.
- a poor solvent such as water is added to the reaction solution to precipitate diphosphine (6) as crystals, and then the resulting crystals
- the method of filtering is mentioned.
- the second reaction step is a step for producing diphosphonium salt (3) by reacting diphosphine (6) with hydroxyphenyl halide (7) in the presence of a nickel compound.
- nickel compound used in the second reaction step examples include nickel chloride (II), nickel bromide (II), nickel iodide (II) and the like. Of these, nickel (II) chloride is preferred.
- the amount of nickel compound used is usually 0.1 to 40 mol%, preferably 1.0 to 30 mol%, more preferably 15 to 25 mol% with respect to 1 mol of diphosphine (6).
- diphosphine (6) used in the second reaction step include 1,4-bis (diphenylphosphine) benzene, 1,4-bis ⁇ di (2-tolyl) phosphine ⁇ benzene, 1,4-bis ⁇ Di (3-tolyl) phosphine ⁇ benzene, 1,4-bis ⁇ di (4-tolyl) phosphine ⁇ benzene, 1,4-bis (P-phenyl-P- (2-tolyl) phosphine) benzene, 1,4 -Bis (P-phenyl-P- (3-tolyl) phosphine) benzene, 1,4-bis (P-phenyl-P- (4-tolyl) phosphine) benzene, 1,1'-bis (diphenylphosphine)- 4,4′-biphenyl, 1,1′-bis (P, P′-di (2-tolyl) phosphine) -4,
- hydroxyphenyl halide (7) used in the second reaction step include chlorophenol, bromophenol, iodophenol and the like. Of these, bromophenol is preferred.
- the amount of hydroxyphenyl halide (7) to be used is generally 2.0 to 5.0 mol, preferably 2.0 to 3.0 mol, more preferably 2.1 to 1 mol per 1 mol of diphosphine (6). 2.3 moles.
- the second reaction step is usually performed in a solvent.
- the solvent to be used is not particularly limited as long as it does not affect the reaction, and usually an aliphatic solvent such as pentane, hexane, heptane, and octane, and an aromatic solvent such as benzene, toluene, xylene, trimethylbenzene, and ethylbenzene.
- Ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol, propanol, butanol, pentanol and ethylene glycol, and water. Among these, alcohol solvents are preferable, and ethylene glycol is particularly preferable.
- the amount of the solvent used is usually 3 parts by weight or more, preferably 4 to 20 parts by weight, more preferably 5 to 8 parts by weight with respect to 1 part by weight of diphosphine (6).
- the mixing order of the nickel compound, diphosphine (6), hydroxyphenyl halide (7) and solvent is not particularly limited.
- hydroxyphenyl halide (7) may be added after mixing nickel compound, diphosphine (6) and solvent, or diphosphine (6) is added after mixing nickel compound, hydroxyphenyl halide (7) and solvent. May be.
- the temperature during the reaction in the second reaction step is usually 150 to 200 ° C, preferably 160 to 190 ° C, more preferably 170 to 180 ° C.
- the third reaction step is a step for producing the diphosphonium salt (1) by reacting the diphosphonium salt (3) obtained in the second reaction step with the compound (8).
- M + represents a hydrogen ion or an alkali metal ion.
- a ⁇ represents BF 4 ⁇ , PF 6 ⁇ , (FSO 2 ) 2 N — or (CF 3 SO 2 ) 2 N — .
- the compound (8) include HBF 4 , HPF 6 , H (FSO 2 ) 2 N, H (CF 3 SO 2 ) 2 N, LiBF 4 , LiPF 6 , Li (FSO 2 ) 2 N, Li ( CF 3 SO 2 ) 2 N, NaBF 4 , NaPF 6 , Na (FSO 2 ) 2 N, Na (CF 3 SO 2 ) 2 N, KBF 4 , KPF 6 , K (FSO 2 ) 2 N, K (CF 3 SO 2 ) 2 N and the like.
- LiBF 4 , LiPF 6 , Li (FSO 2 ) 2 N and Li (CF 3 SO 2 ) 2 N are preferable.
- the amount of compound (8) used is usually 1.6 mol or more, preferably 1.8 to 2.4 mol, more preferably 2.0 to 2.2 mol, relative to 1 mol of phosphonium halide (3). is there.
- the third reaction step is usually performed in a solvent.
- the solvent to be used is not particularly limited as long as it does not affect the reaction between the diphosphonium salt (3) and the compound (8).
- aliphatic solvents such as pentane, hexane, heptane, and octane, benzene , Aromatic solvents such as toluene, xylene, trimethylbenzene and ethylbenzene, ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane, halogen solvents such as dichloromethane, methanol, Examples include alcohols such as ethanol and butanol, nitriles such as acetonitrile, and water.
- an alcohol solvent, a nitrile solvent, a halogen solvent, water, or a mixed solvent thereof is preferable.
- the amount of the solvent to be used is not particularly limited, and is usually 10 parts by weight or less, preferably 5 to 7 parts by weight with respect to 1 part by weight of the diphosphonium salt (3).
- the mixing order of the diphosphonium salt (3), the compound (8) and the solvent is not particularly limited.
- the compound (8) may be added after mixing the diphosphonium salt (3) and the solvent, or the diphosphonium salt (3) may be added after mixing the compound (8) and the solvent.
- the temperature during the reaction in the third reaction step is usually 10 ° C. or higher, preferably 10 to 60 ° C., particularly preferably 10 to 30 ° C.
- the antistatic agent of the present invention contains diphosphonium salt (1) or diphosphonium salt (3) as an active ingredient.
- the diphosphonium salt (1) or the diphosphonium salt (3) can be used alone or as an antistatic agent. Moreover, you may mix and use additives, such as a stabilizer, or a solvent as needed.
- the insulator to be used for the antistatic agent of the present invention include a resin composition. In order to impart antistatic properties, a method of adding the antistatic agent of the present invention to the material of the resin composition at the time of production of the resin composition or the like, or a method of applying to the surface of the resin composition or the like, etc. Can be mentioned.
- the amount of diphosphonium salt (1) or diphosphonium salt (3) added to the resin composition is usually 0.01 to 25% by weight, preferably 1 to 10% by weight, based on 1 part by weight of the resin substrate. Particularly preferred is 1 to 5% by weight.
- additives may be added to the resin composition as long as the properties of the resin composition are not impaired.
- the additive include dyes, pigments, reinforcing agents, fillers, plasticizers, antioxidants, flame retardants, and ultraviolet absorbers.
- the curing accelerator of the present invention is a compound that accelerates the curing reaction between the epoxy resin and the curing agent, and contains a diphosphonium salt (1) or a diphosphonium salt (3) as an active ingredient. They can be used alone or as curing accelerators, and may be mixed with additives such as stabilizers or solvents as necessary.
- the addition amount of the curing accelerator of the present invention is usually from 0.01 to 15% by weight, preferably from 0.01 to 10% by weight, particularly preferably from 1 to 5% by weight, based on the epoxy resin.
- Example 1 A mixed solution of 78.69 g (0.25 mol) of dibromobiphenyl and 624.45 g of tetrahydrofuran was cooled to ⁇ 70 ° C., and 260.63 g (0.60 mol) of a 1.6 mol / l n-BuLi hexane solution was added dropwise to the mixed solution. did. After completion of the dropwise addition of the n-BuLi hexane solution, the reaction mixture was heated to 0 ° C., reacted for another 1 hour, and cooled again to ⁇ 70 ° C. To the reaction mixture, 112.24 g (0.51 mol) of diphenylchlorophosphine was added dropwise.
- Example 2 90.82 g (0.17 mol) of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl obtained in Example 1 was mixed with 66.23 g (0.38 mol) of bromophenol, 622.50 g of ethylene glycol and chloride. The mixture to which 9.52 g (0.03 mol) of nickel hexahydrate was added was reacted at 175 ° C. for 5 hours. The resulting reaction mixture was cooled to room temperature, ion exchanged water was added, and the mixture was extracted with dichloromethane. The obtained organic layer was washed with ion-exchanged water and further concentrated under reduced pressure to obtain a concentrate.
- the obtained concentrate was dissolved in 335.00 g of dichloromethane to obtain a dichloromethane solution.
- the obtained dichloromethane solution was added dropwise to 839.73 g of acetonitrile at room temperature over 1.5 hours.
- the obtained mixture was stirred for 1 hour to precipitate crystals.
- the mixture was filtered to obtain crystals.
- the obtained crystals were washed with acetonitrile and dried under reduced pressure to give 127.09 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide (yield 84.18%).
- 1 H-NMR and 31 P-NMR of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide are shown below.
- Example 3 76.1% bis (trifluoromethanesulfonyl) imide was added to 500.70 g (0.58 mol) of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide obtained in Example 2. 457.74 g (1.21 mol) of a lithium acid aqueous solution, 2012.45 g of dichloromethane and 890.66 g of ion-exchanged water were added, and the mixture was reacted at room temperature for 3 hours.
- an epoxy resin manufactured by Mitsubishi Chemical Corporation, jER828, epoxy equivalent 190
- Curing time was determined by adding heating after the addition of iminobispropylamine and 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, The time (seconds) until stirring became impossible by curing was set. The results are shown in Table 1.
- Example 4 tetraphenylphosphonium bis (trifluoromethanesulfonyl) imide was used instead of 1,1'-bis (4-hydroxyphenyldiphenylphosphonium) -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide.
- the curing time was measured in the same manner as in Example 4 except that. The results are shown in Table 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Epoxy Resins (AREA)
Abstract
The present invention relates to: a diphosphonium salt represented by formula (1) and having a novel cation structure; and a method for producing the diphosphonium salt. The present invention also relates to an antistatic agent and a curing accelerator, each of which contains the diphosphonium salt. Since a diphosphonium salt of the present invention is capable of imparting a polycarbonate resin, a polyvinyl butyral resin and the like with excellent antistatic properties, the diphosphonium salt can be used as an antistatic agent. In addition, a diphosphonium salt of the present invention can be also used as an excellent curing accelerator for thermosetting resins such as epoxy resins.
Description
本発明は、新規なジホスホニウム塩およびその製造方法、ならびに該ジホスホニウム塩を含有する帯電防止剤および硬化促進剤に関する。
The present invention relates to a novel diphosphonium salt, a production method thereof, and an antistatic agent and a curing accelerator containing the diphosphonium salt.
従来、樹脂の帯電防止剤として、テトラフェニルホスホニウム＝ビストリフルオロメタンスルホニルイミドが公知である（特許文献１参照）。また、エポキシ樹脂などの熱硬化性樹脂の硬化促進剤（硬化触媒）として、テトラフェニルホスホニウム＝ブロミドなどが公知である（特許文献２参照）。
Conventionally, tetraphenylphosphonium = bistrifluoromethanesulfonylimide is known as a resin antistatic agent (see Patent Document 1). Further, tetraphenylphosphonium bromide is known as a curing accelerator (curing catalyst) for thermosetting resins such as epoxy resins (see Patent Document 2).
本発明は、樹脂に対して優れた帯電防止性能を付与でき、また、熱硬化性樹脂に対する優れた硬化促進剤となる新規なジホスホニウム塩およびその製造方法、ならびに該ジホスホニウム塩を含有する帯電防止剤および硬化促進剤に関するものである。
The present invention provides a novel diphosphonium salt that can impart excellent antistatic performance to a resin and is an excellent curing accelerator for a thermosetting resin, a method for producing the same, and a charge containing the diphosphonium salt The present invention relates to an inhibitor and a curing accelerator.
本発明者らは、上記課題を解決するために鋭意検討した。その結果、式（１）および式（３）で表わされるジホスホニウム塩が、樹脂に対して優れた帯電防止性能を付与できることを見出した。また、該ジホスホニウム塩が、熱硬化性樹脂に対する優れた硬化促進剤として使用できることを見出し、本発明を完成するに至った。
The present inventors diligently studied to solve the above problems. As a result, it was found that the diphosphonium salts represented by the formulas (1) and (3) can impart excellent antistatic performance to the resin. Further, the inventors have found that the diphosphonium salt can be used as an excellent curing accelerator for thermosetting resins, and have completed the present invention.
即ち、本発明は、式（１）：
That is, the present invention provides the formula (1):
本発明のジホスホニウム塩（１）および（３）は、樹脂に対して優れた帯電防止性を付与できる。また、それらは、熱硬化性樹脂に対する優れた硬化促進剤として使用できるため、有用な化合物である。
The diphosphonium salts (1) and (3) of the present invention can impart excellent antistatic properties to the resin. Further, they are useful compounds because they can be used as excellent curing accelerators for thermosetting resins.
以下、本発明を具体的に説明する。
Hereinafter, the present invention will be specifically described.
式（１）中、Ｒ１およびＲ２は、互いに同一であっても異なっていてもよく、置換基を有していてもよいアリール基を示す。置換基を有していてもよいアリール基として、例えば、フェニル基、２－トリル基、３－トリル基、４－トリル基、２，３－キシリル基、２，４－キシリル基、２，５－キシリル基、２，６－キシリル基、３，４－キシリル基、３，５－キシリル基、２，３，４－トリメチルフェニル基、２，３，５－トリメチルフェニル基、２，３，６－トリメチルフェニル基、２，４，６－トリメチルフェニル基、３，４，５－トリメチルフェニル基、２，３，４，５－テトラメチルフェニル基、２，３，４，６－テトラメチルフェニル基、２，３，５，６－テトラメチルフェニル基、ペンタメチルフェニル基、エチルフェニル基、ｎ－プロピルフェニル基、イソプロピルフェニル基、ｎ－ブチルフェニル基、ｓｅｃ－ブチルフェニル基、ｔｅｒｔ－ブチルフェニル基、ｎ－ペンチルフェニル基、ネオペンチルフェニル基、ｎ－ヘキシルフェニル基、ｎ－オクチルフェニル基、メトキシフェニル基、ジフェニルフェニル基、ナフチル基またはアントラセニル基などが挙げられる。それらの中でフェニル基が好ましい。
In formula (1), R 1 and R 2 may be the same as or different from each other, and each represents an aryl group that may have a substituent. As the aryl group which may have a substituent, for example, phenyl group, 2-tolyl group, 3-tolyl group, 4-tolyl group, 2,3-xylyl group, 2,4-xylyl group, 2,5 -Xylyl group, 2,6-xylyl group, 3,4-xylyl group, 3,5-xylyl group, 2,3,4-trimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6 -Trimethylphenyl group, 2,4,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 2,3,4,5-tetramethylphenyl group, 2,3,4,6-tetramethylphenyl group 2,3,5,6-tetramethylphenyl group, pentamethylphenyl group, ethylphenyl group, n-propylphenyl group, isopropylphenyl group, n-butylphenyl group, sec-butylphenyl group, tert-butyl Phenyl group, n- pentyl phenyl group, neopentyl phenyl group, n- hexylphenyl group, n- octylphenyl group, methoxyphenyl group, diphenyl phenyl group, and naphthyl group or an anthracenyl group. Among them, a phenyl group is preferable.
式（１）中、Ｙは、式（２）：
In formula (1), Y is formula (2):
ジホスホニウム塩（１）の具体的としては、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）ベンゼン＝ビス（トリフルオロメタンスルホニル）イミド、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝ビス（フルオロスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝ビス（フルオロスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝ビス（フルオロスルホニル）イミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝ビス（フルオロスルホニル）イミド、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝ヘキサフルオロホスフェート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝ヘキサフルオロホスフェート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝ヘキサフルオロホスフェート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝ヘキサフルオロホスフェート、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝テトラフルオロボレート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝テトラフルオロボレート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝テトラフルオロボレート、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝テトラフルオロボレート、
Specific examples of the diphosphonium salt (1) include 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl)- P, P′-di (2-tolyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium } Benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, , 4-Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium Benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4-xylyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,5-xylyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4 -Hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (3,4-xylyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-H Roxyphenyl) -P, P'-di (3,5-xylyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5- Trimethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} benzene = Bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4,4 6-trimethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4,5-trimethylphenyl) phosphonium} Benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4,5-tetramethylphenyl) phosphonium} benzene = bis ( Trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4,6-tetramethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) Imido, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5,6-tetra Tilphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) Imido, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-ethylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- ( 4-hydroxyphenyl) -P, P'-di (4-propylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (4-isopropylphenyl) phosphonium} benzene = bis (trifluoromethane Sulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-butylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P -(4-hydroxyphenyl) -P, P'-di (4-sec-butylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P , P′-di (4-tert-butylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-pentyl) Phenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) Enyl) -P, P′-di (4-neopentylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-hexylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-octylphenyl) phosphonium} benzene = bis ( Trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxyphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-Hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphoniu } Benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-naphthylphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-anthracerphenyl) phosphonium} benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- ( 3-Tolyl) phosphonium) benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) benzene = bis (trifluoromethanesulfonyl) imide, 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene = bis (fluoro Sulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2-tolyl) phosphonium} benzene = bis (fluorosulfonyl) imide, 1,4-bis {P- ( 4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} benzene = bis (fluorosulfonyl) imide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-Tolyl) phosphonium} benzene = bis (fluorosulfonyl) imide, 1,4-bis (4-hydroxyphenyldiph Enylphosphonium) benzene = hexafluorophosphate, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} benzene = hexafluorophosphate, 1,4-bis {P -(4-hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene = hexafluorophosphate, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4 -Tolyl) phosphonium} benzene = hexafluorophosphate, 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene = tetrafluoroborate, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (2-tolyl) phosphonium} benzene = tetrafluoroborate, 1,4-bis {P- (4 Hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene = tetrafluoroborate, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-tolyl) phosphonium } Benzene = tetrafluoroborate,
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヘキサフルオロホスフェート、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝テトラフルオロボレート、
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P ′ -Di (2-tolyl) phosphonium} -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (3- Tolyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium}- 4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2, -Xylyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4-xylyl) Phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium}- 4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,6-xylyl) phosphonium} -4,4 '-Biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phos Nium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-xylyl) phosphonium}- 4,4'-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimethylphenyl) phosphonium}- 4,4'-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5-trimethylphenyl) phosphonium}- 4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-to Limethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6 -Trimethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4,5 -Trimethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4) , 5-tetramethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydro Cyphenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- ( 4-hydroxyphenyl) -P, P′-di (2,3,5,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis { P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4- Hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1, '-Bis {P- (4-hydroxyphenyl) -P, P'-di (4-propylphenyl) phosphonium} -4,4'-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis { P- (4-hydroxyphenyl) -P, P′-di (4-isopropylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4 -Hydroxyphenyl) -P, P'-di (4-butylphenyl) phosphonium} -4,4'-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-sec-butylphenyl) phosphonium} -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-pentylphenyl) phosphonium} -4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P— (4-Hydroxyphenyl) -P, P′-di (4-hexylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxyphenyl) phosphonium} -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P -(4-Hydroxyphenyl) -P, P'-di (4-naphthylphenyl) phosphonium} -4,4'-biphenyl bis (trifluoromethanesulfo L) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-anthracerphenyl) phosphonium} -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide, 1,1 ′ -Bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-Hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) -4,4′-biphenyl bis (trifluoromethanesulfonyl) imide 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (fluorosulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P ′ -Di (2-tolyl) phosphonium} -4,4'-biphenyl bis (fluorosulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (3-tolyl) ) Phosphonium} -4,4′-biphenyl = bis (fluorosulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4, 4′-biphenyl bis (fluorosulfonyl) imide, 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl hexafluorophosphine 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} -4,4′-biphenyl = hexafluorophosphate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-biphenyl = hexafluorophosphate, 1,1′-bis {P- (4-hydroxyphenyl) —P, P′-di (4-tolyl) phosphonium} -4,4′-biphenyl = hexafluorophosphate, 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = tetrafluoro Borate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} -4,4′-biphenyl = tetrafluorobo 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-biphenyl = tetrafluoroborate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-biphenyl = tetrafluoroborate,
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－テルフェニル＝ビス（トリフルオロメタンスルホニル）イミド、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝ビス（フルオロスルホニル）イミド、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヘキサフルオロホスフェート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヘキサフルオロホスフェート、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝テトラフルオロボレート、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝テトラフルオロボレートが挙げられる。
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P '-Di (2-tolyl) phosphonium} -4,4'-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di ( 3-Tolyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) Phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′- (2,3-Xylyl) phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2 , 4-Xylyl) phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5 -Xylyl) phosphonium} -4,4'-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) ) Phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4) Xylyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-xylyl) Phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4-trimethylphenyl) ) Phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethyl) Phenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P , P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl)- P, P′-di (3,4,5-trimethylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4'-terphenyl bis (trifluoromethanesulfonyl) imide, , 1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) ) Imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5,6-tetramethylphenyl) phosphonium} -4,4′-terphenyl bis (Trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) ) Imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} -4,4′-terphenyl bis (to Fluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) ) Imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-isopropylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-butylphenyl) phosphonium} -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1 '-Bis {P- (4-hydroxyphenyl) -P, P'-di (4-sec-butylphenyl) phosphonium} -4,4'-terfeny Le = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) phosphonium} -4,4′-terphenyl = Bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium} -4,4'-terphenyl bis ( Trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} -4,4′-terphenyl = bis (trifluoromethane Sulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-hexylphenyl) phosphonium} -4 4'-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-octylphenyl) phosphonium} -4,4'- Terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-methoxyphenyl) phosphonium} -4,4′-terphenyl = Bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-diphenylphenyl) phosphonium} -4,4′-terphenyl bis (Trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-naphthylphenyl) phospho Um} -4,4′-terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-anthracerphenyl) phosphonium} -4,4'-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4,4 '-Terphenyl = bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) -4,4'-terphenyl = Bis (trifluoromethanesulfonyl) imide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphoniu ) -4,4′-terphenyl bis (trifluoromethanesulfonyl) imide, 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl bis (fluorosulfonyl) imide, , 1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} -4,4′-terphenyl bis (fluorosulfonyl) imide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-terphenyl = bis (fluorosulfonyl) imide, 1,1′-bis {P- (4 -Hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-terphenyl = bis (fluorosulfonyl) imide, 1,1′-bis (4-hydro Siphenyldiphenylphosphonium) -4,4′-terphenyl = hexafluorophosphate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} -4, 4′-terphenyl = hexafluorophosphate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-terphenyl = hexafluoro Phosphate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-terphenyl = hexafluorophosphate, 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl = tetrafluoroborate, 1,1′-bis {P- (4-hydroxyphenyl) Nyl) -P, P′-di (2-tolyl) phosphonium} -4,4′-terphenyl = tetrafluoroborate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′- Di (3-tolyl) phosphonium} -4,4′-terphenyl = tetrafluoroborate, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4'-terphenyl = tetrafluoroborate.
式（３）中、Ｘ－はハロゲンイオンを示す。ハロゲンイオンの具体例としては、塩素イオン、臭素イオン、ヨウ素イオンが挙げられる。それらの中で塩素イオンまたは臭素イオンが好ましい。
In the formula (3), X − represents a halogen ion. Specific examples of the halogen ion include chlorine ion, bromine ion and iodine ion. Among them, chlorine ion or bromine ion is preferable.
ジホスホニウム塩（３）の具体例としては、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）ベンゼン＝クロリド、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝クロリド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝クロリド、
Specific examples of the diphosphonium salt (3) include 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2-Tolyl) phosphonium} benzene = chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} benzene = chloride, 1,4-bis {P -(4-hydroxyphenyl) -P, P'-di (4-tolyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3 -Xylyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-xylyl) phosphonium} benzene chloride, 4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,5-xylyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P '-Di (2,6-xylyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} benzene chloride 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,5-xylyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P , P'-di (2,3,4-trimethylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimethyl) Phenyl) Phonon} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,6-trimethylphenyl) phosphonium} benzene chloride, 1,4-bis {P -(4-Hydroxyphenyl) -P, P'-di (2,4,6-trimethylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (3,4,5-trimethylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4,5-tetramethylphenyl) ) Phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} benzene = chloro 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5,6-tetramethylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (pentamethylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-ethylphenyl) ) Phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-propylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4 -Hydroxyphenyl) -P, P'-di (4-isopropylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4 Butylphenyl) phosphonium} benzene = chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-sec-butylphenyl) phosphonium} benzene = chloride, 1,4-bis { P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-Pentylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} benzene chloride, 1,4- Bis {P- (4-hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} benzene chloride, 1,4-bis {P (4-hydroxyphenyl) -P, P'-di (4-octylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxy Phenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} benzene chloride, 1,4-bis {P -(4-hydroxyphenyl) -P, P'-di (4-naphthylphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4- Anthracelphenyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) Zen chloride, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) benzene chloride, 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene chloride, 1,4-bis {P- (4-hydroxyphenyl)- P, P′-di (2-tolyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} benzene chloride, , 4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-tolyl) phosphonium} benzene chloride, 1,4-bis (4-hydroxy) Phenyldiphenylphosphonium) benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2-tolyl) phosphonium} benzene chloride, 1,4-bis {P- (4 -Hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-tolyl) phosphonium} Benzene chloride, 1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2-tolyl) phosphonium} benzene = Chloride, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene = chloride, 1 4- bis {P- (4-hydroxyphenyl) -P, P'-di (4-tolyl) phosphonium} benzene = chloride,
１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）ベンゼン＝ブロミド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）ベンゼン＝ブロミド、
1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} benzene = bromide, , 4-bis {P- (4-hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P ' -Di (4-tolyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium} benzene bromide, 1,4 -Bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-xylyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,5-xylyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} Benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxy Phenyl) -P, P'-di (3,5-xylyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4- Trimethylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium} benzene = bromide, 1,4- {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4,6-trimethylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4,5-trimethylphenyl) ) Phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4,5-tetramethylphenyl) phosphonium} benzene bromide, 1,4 -Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4,6-tetramethylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxy Phenyl) -P, P′-di (2,3,5,6-tetramethylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di ( Pentamethylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} benzene = bromide, 1,4-bis {P -(4-Hydroxyphenyl) -P, P'-di (4-propylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4- Isopropylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-butylphenyl) phosphonium} benzene Bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-sec-butylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) ) -P, P'-di (4-tert-butylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium } Benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-neopentylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4- Hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- (4-Octylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-methoxyphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} benzene bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (4-naphthylphenyl) phosphonium} benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-anthracerphenyl) phosphonium} benzene = bromide, 1,4 -Bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) benzene = bromide, 1,4-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) benzene = bromide, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) Benzene bromide,
１，４－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）ベンゼン＝ヨージド、１，４－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）ベンゼン＝ヨージド、
1,4-bis (4-hydroxyphenyldiphenylphosphonium) benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) phosphonium} benzene = iodide, 1 , 4-bis {P- (4-hydroxyphenyl) -P, P'-di (3-tolyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P ' -Di (4-tolyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium} benzene = iodide, 1,4 -Bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-xylyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,5-xylyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} Benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxy Phenyl) -P, P′-di (3,5-xylyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4- Trimethylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium} benzene iodide, 1,4- {P- (4-hydroxyphenyl) -P, P'-di (2,3,6-trimethylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4,6-trimethylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4,5-trimethylphenyl) ) Phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4,5-tetramethylphenyl) phosphonium} benzene = iodide, 1,4 -Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4,6-tetramethylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxy Phenyl) -P, P′-di (2,3,5,6-tetramethylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di ( Pentamethylphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} benzene = iodide, 1,4-bis {P -(4-Hydroxyphenyl) -P, P'-di (4-propylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4- Isopropylphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-butylphenyl) phosphonium} benzene Iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-sec-butylphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) ) -P, P'-di (4-tert-butylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium } Benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (4-neopentylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4- Hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- (4-Octylphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-methoxyphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P'- Di (4-naphthylphenyl) phosphonium} benzene = iodide, 1,4-bis {P- (4-hydroxyphenyl) -P, P′-di (4-anthracerphenyl) phosphonium} benzene = iodide, 1,4 -Bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) benzene iodide, 1,4-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) benzene iodide, 1,4-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) Benzene iodide,
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝クロリド
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) ) Phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-biphenyl = Chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P— (4-hydroxyphenyl) -P, P′-di (2,3-xylyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-kiri L) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4,4 ′ -Biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} -4,4'-biphenyl chloride, 1,1 ' -Bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (3,5-xylyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4-Trimethylphenyl) phospho Um} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium} -4,4 '-Biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,6-trimethylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4,5-trimethylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4- Hydroxyphenyl) -P, P'- Di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2 , 3,4,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,3) 5,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium}- 4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} -4,4′-biphenyl chloride, 1 , 1'-bis {P (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P '-Di (4-isopropylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-butylphenyl) phosphonium } -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-sec-butylphenyl) phosphonium} -4,4′-biphenyl = Chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-tert-butylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1 ' Bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-neopentylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4 -Hexylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4 '-Biphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxyphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1' -Bi {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} -4,4'-biphenyl chloride, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-naphthylphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-anthracerphenyl) phosphonium} -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4, 4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) -4,4′-biphenyl chloride, 1,1 ′ -Screw{ - (4-hydroxyphenyl) -P- phenyl -P- (4-tolyl) phosphonium) -4,4'-biphenyl = chloride
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝ブロミド
1,1'-bis (4-hydroxyphenyldiphenylphosphonium) -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2-tolyl) ) Phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-biphenyl = Bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P— (4-hydroxyphenyl) -P, P′-di (2,3-xylyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-kiri L) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4,4 ′ -Biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} -4,4'-biphenyl bromide, 1,1 ' -Bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P'-di (3,5-xylyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-Trimethylphenyl) phospho Um} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium} -4,4 '-Biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,6-trimethylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4,5-trimethylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4- Hydroxyphenyl) -P, P'- Di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2 , 3,4,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,3) 5,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium}- 4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} -4,4′-biphenyl bromide, 1 , 1'-bis {P (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P '-Di (4-isopropylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-butylphenyl) phosphonium } -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-sec-butylphenyl) phosphonium} -4,4′-biphenyl = Bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-tert-butylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1 ' Bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-neopentylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4 -Hexylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4 '-Biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxyphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1' -Bi {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} -4,4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-naphthylphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-anthracerphenyl) phosphonium} -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4, 4'-biphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) -4,4'-biphenyl bromide, 1,1 ' -Screw{ - (4-hydroxyphenyl) -P- phenyl -P- (4-tolyl) phosphonium) -4,4'-biphenyl bromides
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝ヨージド
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2-tolyl) ) Phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′-biphenyl = Iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P— (4-hydroxyphenyl) -P, P′-di (2,3-xylyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,4-kiri L) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4,4 ′ -Biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,6-xylyl) phosphonium} -4,4'-biphenyl iodide, 1,1 ' -Bis {P- (4-hydroxyphenyl) -P, P'-di (3,4-xylyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (3,5-xylyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,4-Trimethylphenyl) phospho Um} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium} -4,4 '-Biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,6-trimethylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (3,4,5-trimethylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4- Hydroxyphenyl) -P, P'- Di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2 , 3,4,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,3) 5,6-tetramethylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (pentamethylphenyl) phosphonium}- 4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) phosphonium} -4,4′-biphenyl iodide, 1 , 1'-bis {P (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P '-Di (4-isopropylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-butylphenyl) phosphonium } -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-sec-butylphenyl) phosphonium} -4,4′-biphenyl = Iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1 ′ Bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-neopentylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4 -Hexylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4 '-Biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-methoxyphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1' -Bi {P- (4-hydroxyphenyl) -P, P'-di (3,5-diphenylphenyl) phosphonium} -4,4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-naphthylphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-anthracerphenyl) phosphonium} -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4, 4'-biphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (3-tolyl) phosphonium) -4,4'-biphenyl iodide, 1,1 ' -Screw{ - (4-hydroxyphenyl) -P- phenyl -P- (4-tolyl) phosphonium) -4,4'-biphenyl = iodide
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－テルフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝クロリド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝クロリド、
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2- Tolyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′- Terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-terphenyl chloride, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P'-di (2 4-Xylyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4 , 4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,6-xylyl) phosphonium} -4,4′-terphenyl chloride 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4-xylyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis { P- (4-hydroxyphenyl) -P, P′-di (3,5-xylyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimmer Ruphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium}- 4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} -4,4′- Terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4,5-trimethylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′- Screw {P- (4-H Droxyphenyl) -P, P'-di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5,6-tetramethylphenyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P , P′-di (pentamethylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) ) Phosphonium} -4,4'-te Phenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (4-isopropylphenyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) ) -P, P′-di (4-butylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-sec-butylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) Phosphoni -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-pentylphenyl) phosphonium} -4,4'-ter Phenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1 ′ -Bis {P- (4-hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-Methoxyphenyl) pho Sufonium} -4,4′-terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-diphenylphenyl) phosphonium} -4,4 ′ Terphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-naphthylphenyl) phosphonium} -4,4′-terphenyl chloride, 1,1 '-Bis {P- (4-hydroxyphenyl) -P, P'-di (4-anthracerphenyl) phosphonium} -4,4'-terphenyl chloride, 1,1'-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4,4'-terphenyl chloride, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P -(3-tri ) Phosphonium) -4,4′-biphenyl chloride, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) -4,4′-biphenyl = Chloride,
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－テルフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝ブロミド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝ブロミド、
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2- Tolyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′- Terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-terphenyl bromide, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P'-di (2 4-Xylyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4 , 4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,6-xylyl) phosphonium} -4,4′-terphenyl bromide 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4-xylyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis { P- (4-hydroxyphenyl) -P, P′-di (3,5-xylyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimmer Ruphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium}- 4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} -4,4′- Terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4,5-trimethylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′- Screw {P- (4-H Droxyphenyl) -P, P'-di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5,6-tetramethylphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P , P′-di (pentamethylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) ) Phosphonium} -4,4'-te Phenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (4-isopropylphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) ) -P, P′-di (4-butylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-sec-butylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) Phosphoni M} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-pentylphenyl) phosphonium} -4,4′-ter Phenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1 ′ -Bis {P- (4-hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-Methoxyphenyl) pho Sufonium} -4,4′-terphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-diphenylphenyl) phosphonium} -4,4 ′ -Terphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P, P'-di (4-naphthylphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1 '-Bis {P- (4-hydroxyphenyl) -P, P'-di (4-anthracerphenyl) phosphonium} -4,4'-terphenyl bromide, 1,1'-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4,4'-terphenyl bromide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P -(3-tri ) Phosphonium) -4,4′-biphenyl bromide, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) -4,4′-biphenyl = Bromide,
１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－トリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４－キリシル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，６－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－キシリル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，４，６－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，４，５－トリメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，５－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，４，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（２，３，５，６－テトラメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（ペンタメチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－エチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－プロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－イソプロピルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｓｅｃ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ｔｅｒｔ－ブチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ネオペンチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ヘキシルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－オクチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－メトキシフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（３，５－ジフェニルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－ナフチルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ，Ｐ’－ジ（４－アントラセルフェニル）ホスホニウム｝－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（２－トリル）ホスホニウム）－４，４’－テルフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（３－トリル）ホスホニウム）－４，４’－ビフェニル＝ヨージド、１，１’－ビス｛Ｐ－（４－ヒドロキシフェニル）－Ｐ－フェニル－Ｐ－（４－トリル）ホスホニウム）－４，４’－ビフェニル＝ヨージドが挙げられる。
1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2- Tolyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3-tolyl) phosphonium} -4,4′- Terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tolyl) phosphonium} -4,4′-terphenyl iodide, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (2,3-xylyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P'-di (2 4-Xylyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,5-xylyl) phosphonium} -4 , 4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,6-xylyl) phosphonium} -4,4′-terphenyl iodide 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4-xylyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis { P- (4-hydroxyphenyl) -P, P′-di (3,5-xylyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,4-trimmer Ruphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,5-trimethylphenyl) phosphonium}- 4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,3,6-trimethylphenyl) phosphonium} -4,4′- Terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (2,4,6-trimethylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,4,5-trimethylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′- Screw {P- (4-H Droxyphenyl) -P, P'-di (2,3,4,5-tetramethylphenyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (2,3,4,6-tetramethylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P'-di (2,3,5,6-tetramethylphenyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P , P′-di (pentamethylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-ethylphenyl) ) Phosphonium} -4,4'-te Phenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-propylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′- Bis {P- (4-hydroxyphenyl) -P, P'-di (4-isopropylphenyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) ) -P, P′-di (4-butylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di ( 4-sec-butylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-tert-butylphenyl) Phosphoni } -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-pentylphenyl) phosphonium} -4,4′-ter Phenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-neopentylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1 ′ -Bis {P- (4-hydroxyphenyl) -P, P'-di (4-hexylphenyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxy Phenyl) -P, P′-di (4-octylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-Methoxyphenyl) pho Sufonium} -4,4′-terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (3,5-diphenylphenyl) phosphonium} -4,4 ′ Terphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P, P′-di (4-naphthylphenyl) phosphonium} -4,4′-terphenyl iodide, 1,1 '-Bis {P- (4-hydroxyphenyl) -P, P'-di (4-anthracerphenyl) phosphonium} -4,4'-terphenyl iodide, 1,1'-bis {P- (4 -Hydroxyphenyl) -P-phenyl-P- (2-tolyl) phosphonium) -4,4'-terphenyl iodide, 1,1'-bis {P- (4-hydroxyphenyl) -P-phenyl-P -(3-tri ) Phosphonium) -4,4′-biphenyl iodide, 1,1′-bis {P- (4-hydroxyphenyl) -P-phenyl-P- (4-tolyl) phosphonium) -4,4′-biphenyl = Iodide.
本発明のジホスホニウム塩（３）は、次の２つの工程により製造できる。
まず、有機リチウム化合物の存在下、式（４）： The diphosphonium salt (3) of the present invention can be produced by the following two steps.
First, in the presence of an organolithium compound, the formula (4):
まず、有機リチウム化合物の存在下、式（４）： The diphosphonium salt (3) of the present invention can be produced by the following two steps.
First, in the presence of an organolithium compound, the formula (4):
式（５）：
Ｘ－Ｙ－Ｘ （５）
（式中、ＹおよびＸは前記に同じ。）で表されるアリールジハライド（以下、アリールジハライド（５）という。）を反応させて、式（６）：
Formula (5):
XYX (5)
(Wherein Y and X are the same as defined above) are reacted with an aryl dihalide (hereinafter referred to as aryl dihalide (5)) to give a formula (6):
次に、第１反応工程で得られたジホスフィン（６）を、ニッケル化合物の存在下で、式（７）：
Next, diphosphine (6) obtained in the first reaction step is converted to formula (7) in the presence of a nickel compound:
また、本発明のジホスホニウム塩（１）は、前記ジホスホニウム塩（３）を、式（８）：
Ｍ＋・Ａ－ （８）
（式中、Ｍ＋は水素イオンまたはアルカリ金属イオンを示す。Ａ－は前記と同じ。）で表される化合物（以下、化合物（８）という。）と反応させて製造する（以下、第３反応工程という。）。 Further, the diphosphonium salt (1) of the present invention is obtained by converting the diphosphonium salt (3) into the formula (8):
M +・ A − (8)
(In the formula, M + represents a hydrogen ion or an alkali metal ion. A − is the same as above.) (Hereinafter, referred to as a compound (8)). Called the reaction step).
Ｍ＋・Ａ－ （８）
（式中、Ｍ＋は水素イオンまたはアルカリ金属イオンを示す。Ａ－は前記と同じ。）で表される化合物（以下、化合物（８）という。）と反応させて製造する（以下、第３反応工程という。）。 Further, the diphosphonium salt (1) of the present invention is obtained by converting the diphosphonium salt (3) into the formula (8):
M +・ A − (8)
(In the formula, M + represents a hydrogen ion or an alkali metal ion. A − is the same as above.) (Hereinafter, referred to as a compound (8)). Called the reaction step).
第１反応工程について説明する。
第１反応工程は、有機リチウム化合物の存在下、ハロジアリールホスフィン（４）とアリールジハライド（５）を反応させてジホスフィン（６）を製造する工程である。 The first reaction step will be described.
The first reaction step is a step of producing diphosphine (6) by reacting halodiarylphosphine (4) and aryl dihalide (5) in the presence of an organolithium compound.
第１反応工程は、有機リチウム化合物の存在下、ハロジアリールホスフィン（４）とアリールジハライド（５）を反応させてジホスフィン（６）を製造する工程である。 The first reaction step will be described.
The first reaction step is a step of producing diphosphine (6) by reacting halodiarylphosphine (4) and aryl dihalide (5) in the presence of an organolithium compound.
第１反応工程で使用するハロジアリールホスフィン（４）の具体例としては、ジフェニルクロロホスフィン、ジ（２－トリル）クロロホスフィン、ジ（３－トリル）クロロホスフィン、ジ（４－トリル）クロロホスフィン、Ｐ－フェニル－Ｐ－（２－トリル）クロロホスフィン、Ｐ－フェニル－Ｐ－（３－トリル）クロロホスフィン、Ｐ－フェニル－Ｐ－（４－トリル）クロロホスフィン、ジフェニルブロモホスフィン、ジ（２－トリル）ブロモホスフィン、ジ（３－トリル）ブロモホスフィン、ジ（４－トリル）ブロモホスフィン、Ｐ－フェニル－Ｐ－（２－トリル）ブロモホスフィン、Ｐ－フェニル－Ｐ－（３－トリル）ブロモホスフィン、Ｐ－フェニル－Ｐ－（４－トリル）ブロモホスフィン、ジフェニルヨードホスフィン、ジ（２－トリル）ヨードホスフィン、ジ（３－トリル）ヨードホスフィン、ジ（４－トリル）ヨードホスフィン、Ｐ－フェニル－Ｐ－（２－トリル）ヨードホスフィン、Ｐ－フェニル－Ｐ－（３－トリル）ヨードホスフィン、Ｐ－フェニル－Ｐ－（４－トリル）ヨードホスフィンなどが挙げられる。それらの中で、ジフェニルクロロホスフィンが好ましい。
Specific examples of the halodiarylphosphine (4) used in the first reaction step include diphenylchlorophosphine, di (2-tolyl) chlorophosphine, di (3-tolyl) chlorophosphine, di (4-tolyl) chlorophosphine, P-phenyl-P- (2-tolyl) chlorophosphine, P-phenyl-P- (3-tolyl) chlorophosphine, P-phenyl-P- (4-tolyl) chlorophosphine, diphenylbromophosphine, di (2- Tolyl) bromophosphine, di (3-tolyl) bromophosphine, di (4-tolyl) bromophosphine, P-phenyl-P- (2-tolyl) bromophosphine, P-phenyl-P- (3-tolyl) bromophosphine , P-phenyl-P- (4-tolyl) bromophosphine, diphenyliodophosphine, di (2 Tolyl) iodophosphine, di (3-tolyl) iodophosphine, di (4-tolyl) iodophosphine, P-phenyl-P- (2-tolyl) iodophosphine, P-phenyl-P- (3-tolyl) iodophosphine P-phenyl-P- (4-tolyl) iodophosphine and the like. Of these, diphenylchlorophosphine is preferred.
第１反応工程で使用する有機リチウム化合物の具体例としては、メチルリチウム、エチルリチウム、イソプロピルリチウム、ｎ－ブチルリチウム、ｓｅｃ－ブチルリチウム、フェニルリチウム、ベンジルリチウムなどが挙げられる。それらの中で、ｎ－ブチルリチウムが好ましい。
Specific examples of the organic lithium compound used in the first reaction step include methyl lithium, ethyl lithium, isopropyl lithium, n-butyl lithium, sec-butyl lithium, phenyl lithium, benzyl lithium and the like. Of these, n-butyllithium is preferred.
前記有機リチウム化合物の使用量は、アリールジハライド（５）１モルに対して、通常、２～１０モル、好ましくは３～７モル、より好ましくは４～５モルである。
The amount of the organolithium compound used is usually 2 to 10 mol, preferably 3 to 7 mol, more preferably 4 to 5 mol, per 1 mol of the aryl dihalide (5).
第１反応工程で使用するアリールジハライド（５）の具体例としては、１，４－ジクロロベンゼン、１－ブロモ－４－クロロベンゼン、１－クロロー４－ヨードベンゼン、１，４－ジブロモベンゼン、１－ブロモ－４－ヨードベンゼン、１，４－ジヨードベンゼン、４，４’－ジクロロビフェニル、４－ブロモ－４’－クロロビフェニル、４－クロロー４’－ヨードビフェニル、４，４’－ジブロモビフェニル、４－ブロモ－４’－ヨードビフェニル、４，４’－ジヨードビフェニル、４，４’－ジクロロテルフェニル、４－ブロモ－４’－クロロテルフェニル、４－クロロー４’－ヨードテルフェニル、４，４’－ジブロモテルフェニル、４－ブロモ－４’－ヨードテルフェニル、４，４’－ジヨードテルフェニルが挙げられる。それらの中で、４，４’－ジブロモビフェニルが好ましい。アリールジハライド（５）の使用量は、ハロジアリールホスフィン（４）１モルに対して、通常、０．２～０．５モル、好ましくは０．３～０．５モル、より好ましくは０．４～０．５モルである。
Specific examples of the aryl dihalide (5) used in the first reaction step include 1,4-dichlorobenzene, 1-bromo-4-chlorobenzene, 1-chloro-4-iodobenzene, 1,4-dibromobenzene, 1 -Bromo-4-iodobenzene, 1,4-diiodobenzene, 4,4'-dichlorobiphenyl, 4-bromo-4'-chlorobiphenyl, 4-chloro-4'-iodobiphenyl, 4,4'-dibromobiphenyl 4-bromo-4′-iodobiphenyl, 4,4′-diiodobiphenyl, 4,4′-dichloroterphenyl, 4-bromo-4′-chloroterphenyl, 4-chloro-4′-iodotephenyl, Examples include 4,4′-dibromoterphenyl, 4-bromo-4′-iodoterphenyl, and 4,4′-diioterterphenyl. Of these, 4,4'-dibromobiphenyl is preferred. The amount of the aryl dihalide (5) to be used is generally 0.2 to 0.5 mol, preferably 0.3 to 0.5 mol, more preferably 0.00 mol, per 1 mol of the halodiarylphosphine (4). 4 to 0.5 mol.
第１反応工程は、通常、溶媒中で行う。使用する溶媒は、反応に影響しないものであれば特に限定されず、通常、ペンタン、ヘキサン、ヘプタン、オクタンなどの脂肪族系溶媒、ベンゼン、トルエン、キシレン、トリメチルベンゼン、エチルベンゼンなどの芳香族系溶媒、ジエチルエーテル、ジイソプロピルエーテル、ｔｅｒｔ－ブチルメチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、ジオキサンなどのエーテル系溶媒である。それらの中で、エーテル系溶媒が好ましく、テトラヒドロフランが特に好ましい。使用する溶媒の量は、アリールジハライド（５）１重量部に対し、通常、３重量部以上、好ましくは３～１０重量部、より好ましくは６～８重量部である。
The first reaction step is usually performed in a solvent. The solvent to be used is not particularly limited as long as it does not affect the reaction, and usually an aliphatic solvent such as pentane, hexane, heptane, and octane, and an aromatic solvent such as benzene, toluene, xylene, trimethylbenzene, and ethylbenzene. Ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane. Among them, ether solvents are preferable, and tetrahydrofuran is particularly preferable. The amount of the solvent used is usually 3 parts by weight or more, preferably 3 to 10 parts by weight, more preferably 6 to 8 parts by weight with respect to 1 part by weight of the aryl dihalide (5).
第１反応工程の反応は、通常、アリールジハライド（５）と溶媒を混合した混合溶液に対して有機リチウム化合物を添加し、さらにハロジアリールホスフィン（４）を添加して行う。アリールジハライド（５）と有機リチウム化合物との反応時の温度は、通常、－９０～－４０℃、好ましくは－８０～－６０℃、より好ましくは－８０～－７０℃である。また、アリールジハライド（５）と有機リチウム化合物との反応生成物とハロジアリールホスフィン（４）との反応時の温度は、通常、－９０℃～－４０℃、好ましくは－８０～－６０℃、より好ましくは－８０℃～－７０℃である。
The reaction in the first reaction step is usually performed by adding an organolithium compound to a mixed solution in which an aryl dihalide (5) and a solvent are mixed, and further adding a halodiarylphosphine (4). The temperature during the reaction between the aryl dihalide (5) and the organolithium compound is usually −90 to −40 ° C., preferably −80 to −60 ° C., more preferably −80 to −70 ° C. The reaction temperature of the reaction product of aryl dihalide (5) and organolithium compound with halodiarylphosphine (4) is usually −90 ° C. to −40 ° C., preferably −80 to −60 ° C. More preferably, it is −80 ° C. to −70 ° C.
第１反応工程の反応終了後の反応液からジホスフィン（６）を取出す方法としては、例えば、反応液に水などの貧溶媒を加えてジホスフィン（６）を結晶として析出させた後、生じた結晶をろ過する方法が挙げられる。
As a method for taking out diphosphine (6) from the reaction solution after completion of the reaction in the first reaction step, for example, a poor solvent such as water is added to the reaction solution to precipitate diphosphine (6) as crystals, and then the resulting crystals The method of filtering is mentioned.
次に、第２反応工程について説明する。
第２反応工程は、ニッケル化合物の存在下、ジホスフィン（６）とヒドロキシフェニルハライド（７）を反応させて、ジホスホニウム塩（３）を製造する工程である。 Next, the second reaction step will be described.
The second reaction step is a step for producing diphosphonium salt (3) by reacting diphosphine (6) with hydroxyphenyl halide (7) in the presence of a nickel compound.
第２反応工程は、ニッケル化合物の存在下、ジホスフィン（６）とヒドロキシフェニルハライド（７）を反応させて、ジホスホニウム塩（３）を製造する工程である。 Next, the second reaction step will be described.
The second reaction step is a step for producing diphosphonium salt (3) by reacting diphosphine (6) with hydroxyphenyl halide (7) in the presence of a nickel compound.
第２反応工程で使用するニッケル化合物の具体的としては、塩化ニッケル（ＩＩ）、臭化ニッケル（ＩＩ）、ヨウ化ニッケル（ＩＩ）などが挙げられる。それらの中で、塩化ニッケル（ＩＩ）が好ましい。
Specific examples of the nickel compound used in the second reaction step include nickel chloride (II), nickel bromide (II), nickel iodide (II) and the like. Of these, nickel (II) chloride is preferred.
ニッケル化合物の使用量は、ジホスフィン（６）１モルに対して、通常、０．１～４０モル％、好ましくは１．０～３０モル％、より好ましくは１５～２５モル％である。
The amount of nickel compound used is usually 0.1 to 40 mol%, preferably 1.0 to 30 mol%, more preferably 15 to 25 mol% with respect to 1 mol of diphosphine (6).
第２反応工程で使用するジホスフィン（６）の具体例としては、１，４－ビス（ジフェニルホスフィン）ベンゼン、１，４－ビス｛ジ（２－トリル）ホスフィン｝ベンゼン、１，４－ビス｛ジ（３－トリル）ホスフィン｝ベンゼン、１，４－ビス｛ジ（４－トリル）ホスフィン｝ベンゼン、１，４－ビス（Ｐ－フェニル－Ｐ－（２－トリル）ホスフィン）ベンゼン、１，４－ビス（Ｐ－フェニル－Ｐ－（３－トリル）ホスフィン）ベンゼン、１，４－ビス（Ｐ－フェニル－Ｐ－（４－トリル）ホスフィン）ベンゼン、１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（２－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（３－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（４－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（２－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（３－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（４－トリル）ホスフィン）－４，４’－ビフェニル、１，１’－ビス（ジフェニルホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（２－トリル）ホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（３－トリル）ホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ，Ｐ’－ジ（４－トリル）ホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（２－トリル）ホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（３－トリル）ホスフィン）－４，４’－テルフェニル、１，１’－ビス（Ｐ－フェニル－Ｐ’－（４－トリル）ホスフィン）－４，４’－テルフェニルなどが挙げられる。それらの中で、１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニルが好ましい。
Specific examples of diphosphine (6) used in the second reaction step include 1,4-bis (diphenylphosphine) benzene, 1,4-bis {di (2-tolyl) phosphine} benzene, 1,4-bis { Di (3-tolyl) phosphine} benzene, 1,4-bis {di (4-tolyl) phosphine} benzene, 1,4-bis (P-phenyl-P- (2-tolyl) phosphine) benzene, 1,4 -Bis (P-phenyl-P- (3-tolyl) phosphine) benzene, 1,4-bis (P-phenyl-P- (4-tolyl) phosphine) benzene, 1,1'-bis (diphenylphosphine)- 4,4′-biphenyl, 1,1′-bis (P, P′-di (2-tolyl) phosphine) -4,4′-biphenyl, 1,1′-bis (P, P′-di (3 -Tolyl) phosphine) -4, '-Biphenyl, 1,1'-bis (P, P'-di (4-tolyl) phosphine) -4,4'-biphenyl, 1,1'-bis (P-phenyl-P'-(2-tolyl) ) Phosphine) -4,4′-biphenyl, 1,1′-bis (P-phenyl-P ′-(3-tolyl) phosphine) -4,4′-biphenyl, 1,1′-bis (P-phenyl) -P '-(4-Tolyl) phosphine) -4,4'-biphenyl, 1,1'-bis (diphenylphosphine) -4,4'-terphenyl, 1,1'-bis (P, P'- Di (2-tolyl) phosphine) -4,4′-terphenyl, 1,1′-bis (P, P′-di (3-tolyl) phosphine) -4,4′-terphenyl, 1,1 ′ -Bis (P, P'-di (4-tolyl) phosphine) -4,4'-terphenyl, 1,1 ' Bis (P-phenyl-P '-(2-tolyl) phosphine) -4,4'-terphenyl, 1,1'-bis (P-phenyl-P'-(3-tolyl) phosphine) -4,4 Examples include '-terphenyl, 1,1'-bis (P-phenyl-P'-(4-tolyl) phosphine) -4,4'-terphenyl. Of these, 1,1'-bis (diphenylphosphine) -4,4'-biphenyl is preferred.
第２反応工程で使用するヒドロキシフェニルハライド（７）の具体例としては、クロロフェノール、ブロモフェノール、ヨードフェノールなどが挙げられる。それらの中で、ブロモフェノールが好ましい。ヒドロキシフェニルハライド（７）の使用量は、ジホスフィン（６）１モルに対して、通常、２．０～５．０モル、好ましくは２．０～３．０モル、より好ましくは２．１～２．３モルである。
Specific examples of hydroxyphenyl halide (7) used in the second reaction step include chlorophenol, bromophenol, iodophenol and the like. Of these, bromophenol is preferred. The amount of hydroxyphenyl halide (7) to be used is generally 2.0 to 5.0 mol, preferably 2.0 to 3.0 mol, more preferably 2.1 to 1 mol per 1 mol of diphosphine (6). 2.3 moles.
第２反応工程は、通常、溶媒中で行う。使用する溶媒は、反応に影響しないものであれば特に限定されず、通常、ペンタン、ヘキサン、ヘプタン、オクタンなどの脂肪族系溶媒、ベンゼン、トルエン、キシレン、トリメチルベンゼン、エチルベンゼンなどの芳香族系溶媒、ジエチルエーテル、ジイソプロピルエーテル、ｔｅｒｔ－ブチルメチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、ジオキサンなどのエーテル系溶媒、メタノール、エタノール、プロパノール、ブタノール、ペンタノール、エチレングリコールなどのアルコール系溶媒、水である。それらの中で、アルコール系溶媒が好ましく、エチレングリコールが特に好ましい。使用する溶媒の量は、ジホスフィン（６）１重量部に対し、通常、３重量部以上、好ましくは４～２０重量部、より好ましくは５～８重量部である。
The second reaction step is usually performed in a solvent. The solvent to be used is not particularly limited as long as it does not affect the reaction, and usually an aliphatic solvent such as pentane, hexane, heptane, and octane, and an aromatic solvent such as benzene, toluene, xylene, trimethylbenzene, and ethylbenzene. Ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane, alcohol solvents such as methanol, ethanol, propanol, butanol, pentanol and ethylene glycol, and water. Among these, alcohol solvents are preferable, and ethylene glycol is particularly preferable. The amount of the solvent used is usually 3 parts by weight or more, preferably 4 to 20 parts by weight, more preferably 5 to 8 parts by weight with respect to 1 part by weight of diphosphine (6).
第２反応工程の反応において、ニッケル化合物、ジホスフィン（６）、ヒドロキシフェニルハライド（７）および溶媒の混合順序は特に限定されない。例えば、ニッケル化合物、ジホスフィン（６）および溶媒を混合した後にヒドロキシフェニルハライド（７）を添加してもよいし、ニッケル化合物、ヒドロキシフェニルハライド（７）および溶媒を混合した後にジホスフィン（６）を添加してもよい。第２反応工程の反応時の温度は、通常、１５０～２００℃、好ましくは１６０～１９０℃、より好ましくは１７０～１８０℃である。
In the reaction of the second reaction step, the mixing order of the nickel compound, diphosphine (6), hydroxyphenyl halide (7) and solvent is not particularly limited. For example, hydroxyphenyl halide (7) may be added after mixing nickel compound, diphosphine (6) and solvent, or diphosphine (6) is added after mixing nickel compound, hydroxyphenyl halide (7) and solvent. May be. The temperature during the reaction in the second reaction step is usually 150 to 200 ° C, preferably 160 to 190 ° C, more preferably 170 to 180 ° C.
第２反応工程の反応終了後の反応液からジホスホニウム塩（３）を取出す方法としては、例えば、反応液に水などの貧溶媒を添加した後、ジクロロメタンなどの有機溶媒などを加えてジホスホニウム塩（３）を抽出する方法が挙げられる。
As a method for removing the diphosphonium salt (3) from the reaction solution after completion of the reaction in the second reaction step, for example, after adding a poor solvent such as water to the reaction solution, an organic solvent such as dichloromethane is added to diphosphonium. The method of extracting salt (3) is mentioned.
最後に、第３反応工程について説明する。
第３反応工程は、第２反応工程で得たジホスホニウム塩（３）と化合物（８）を反応させて、ジホスホニウム塩（１）を製造する工程である。 Finally, the third reaction step will be described.
The third reaction step is a step for producing the diphosphonium salt (1) by reacting the diphosphonium salt (3) obtained in the second reaction step with the compound (8).
第３反応工程は、第２反応工程で得たジホスホニウム塩（３）と化合物（８）を反応させて、ジホスホニウム塩（１）を製造する工程である。 Finally, the third reaction step will be described.
The third reaction step is a step for producing the diphosphonium salt (1) by reacting the diphosphonium salt (3) obtained in the second reaction step with the compound (8).
式（８）中、Ｍ＋は、水素イオンまたはアルカリ金属イオンを示す。Ａ－は、ＢＦ４
－、ＰＦ６
－、（ＦＳＯ２）２Ｎ－または（ＣＦ３ＳＯ２）２Ｎ－を示す。化合物（８）の具体例としては、ＨＢＦ４、ＨＰＦ６、Ｈ（ＦＳＯ２）２Ｎ、Ｈ（ＣＦ３ＳＯ２）２Ｎ、ＬｉＢＦ４、ＬｉＰＦ６、Ｌｉ（ＦＳＯ２）２Ｎ、Ｌｉ（ＣＦ３ＳＯ２）２Ｎ、ＮａＢＦ４、ＮａＰＦ６、Ｎａ（ＦＳＯ２）２Ｎ、Ｎａ（ＣＦ３ＳＯ２）２Ｎ、ＫＢＦ４、ＫＰＦ６、Ｋ（ＦＳＯ２）２Ｎ、Ｋ（ＣＦ３ＳＯ２）２Ｎなどが挙げられる。それらの中で、ＬｉＢＦ４、ＬｉＰＦ６、Ｌｉ（ＦＳＯ２）２ＮおよびＬｉ（ＣＦ３ＳＯ２）２Ｎが好ましい。
In formula (8), M + represents a hydrogen ion or an alkali metal ion. A − represents BF 4 − , PF 6 − , (FSO 2 ) 2 N — or (CF 3 SO 2 ) 2 N — . Specific examples of the compound (8) include HBF 4 , HPF 6 , H (FSO 2 ) 2 N, H (CF 3 SO 2 ) 2 N, LiBF 4 , LiPF 6 , Li (FSO 2 ) 2 N, Li ( CF 3 SO 2 ) 2 N, NaBF 4 , NaPF 6 , Na (FSO 2 ) 2 N, Na (CF 3 SO 2 ) 2 N, KBF 4 , KPF 6 , K (FSO 2 ) 2 N, K (CF 3 SO 2 ) 2 N and the like. Among them, LiBF 4 , LiPF 6 , Li (FSO 2 ) 2 N and Li (CF 3 SO 2 ) 2 N are preferable.
化合物（８）の使用量は、通常、ホスホニウムハライド（３）１モルに対して１．６モル以上、好ましくは１．８～２．４モル、より好ましくは２．０～２．２モルである。
The amount of compound (8) used is usually 1.6 mol or more, preferably 1.8 to 2.4 mol, more preferably 2.0 to 2.2 mol, relative to 1 mol of phosphonium halide (3). is there.
第３反応工程は、通常、溶媒中で行われる。使用する溶媒は、ジホスホニウム塩（３）と化合物（８）との反応に影響を与えないものであれば特に限定されず、通常、ペンタン、ヘキサン、ヘプタン、オクタンなどの脂肪族系溶媒、ベンゼン、トルエン、キシレン、トリメチルベンゼン、エチルベンゼンなどの芳香族系溶媒、ジエチルエーテル、ジイソプロピルエーテル、ｔｅｒｔ－ブチルメチルエーテル、シクロペンチルメチルエーテル、テトラヒドロフラン、ジオキサンなどのエーテル系溶媒、ジクロロメタンなどのハロゲン系溶媒、メタノール、エタノール、ブタノールなどのアルコール類、アセトニトリルなどのニトリル類または水が挙げられる。それらの中で、アルコール系溶媒、ニトリル系溶媒、ハロゲン系溶媒、水またはこれらの混合溶媒が好ましい。使用する溶媒の使用量は特に制限はなく、ジホスホニウム塩（３）１重量部に対して、通常、１０重量部以下、好ましくは５～７重量部である。
The third reaction step is usually performed in a solvent. The solvent to be used is not particularly limited as long as it does not affect the reaction between the diphosphonium salt (3) and the compound (8). Usually, aliphatic solvents such as pentane, hexane, heptane, and octane, benzene , Aromatic solvents such as toluene, xylene, trimethylbenzene and ethylbenzene, ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, cyclopentyl methyl ether, tetrahydrofuran and dioxane, halogen solvents such as dichloromethane, methanol, Examples include alcohols such as ethanol and butanol, nitriles such as acetonitrile, and water. Among them, an alcohol solvent, a nitrile solvent, a halogen solvent, water, or a mixed solvent thereof is preferable. The amount of the solvent to be used is not particularly limited, and is usually 10 parts by weight or less, preferably 5 to 7 parts by weight with respect to 1 part by weight of the diphosphonium salt (3).
第３反応工程において、ジホスホニウム塩（３）、化合物（８）および溶媒の混合順序は特に限定されない。例えば、ジホスホニウム塩（３）と溶媒を混合した後に化合物（８）を添加してもよいし、化合物（８）と溶媒を混合した後にジホスホニウム塩（３）を添加してもよい。
In the third reaction step, the mixing order of the diphosphonium salt (3), the compound (8) and the solvent is not particularly limited. For example, the compound (8) may be added after mixing the diphosphonium salt (3) and the solvent, or the diphosphonium salt (3) may be added after mixing the compound (8) and the solvent.
第３反応工程の反応時の温度は、通常、１０℃以上、好ましくは１０～６０℃、特に好ましくは１０～３０℃である。
The temperature during the reaction in the third reaction step is usually 10 ° C. or higher, preferably 10 to 60 ° C., particularly preferably 10 to 30 ° C.
反応終了後の反応液からジホスホニウム塩（１）を取り出す方法としては、以下の方法が挙げられる。（ｉ）反応液が分液している場合：反応液を分液後、得られた有機層を水洗し、濃縮、乾燥してジホスホニウム塩（１）を得る。（ｉｉ）反応液が分液していない場合：反応液を濃縮後、ろ過、乾燥してジホスホニウム塩（１）を得る。
As a method for taking out the diphosphonium salt (1) from the reaction solution after completion of the reaction, the following methods may be mentioned. (I) When the reaction solution is separated: After separating the reaction solution, the obtained organic layer is washed with water, concentrated and dried to obtain the diphosphonium salt (1). (Ii) When the reaction solution is not separated: The reaction solution is concentrated, filtered and dried to obtain the diphosphonium salt (1).
本発明の帯電防止剤は、ジホスホニウム塩（１）またはジホスホニウム塩（３）を有効成分として含有するものである。ジホスホニウム塩（１）またはジホスホニウム塩（３）は、単独であっても帯電防止剤として使用できる。また、必要に応じて安定化剤などの添加剤または溶媒などを混合して使用してもよい。本発明の帯電防止剤の使用対象となる絶縁物としては、樹脂組成物などが挙げられる。帯電防止性を付与するには、本発明の帯電防止剤を樹脂組成物などの製造時に、樹脂組成物の材料に添加して混合する方法、または樹脂組成物などの表面に塗布する方法などが挙げられる。
The antistatic agent of the present invention contains diphosphonium salt (1) or diphosphonium salt (3) as an active ingredient. The diphosphonium salt (1) or the diphosphonium salt (3) can be used alone or as an antistatic agent. Moreover, you may mix and use additives, such as a stabilizer, or a solvent as needed. Examples of the insulator to be used for the antistatic agent of the present invention include a resin composition. In order to impart antistatic properties, a method of adding the antistatic agent of the present invention to the material of the resin composition at the time of production of the resin composition or the like, or a method of applying to the surface of the resin composition or the like, etc. Can be mentioned.
樹脂組成物に対するジホスホニウム塩（１）またはジホスホニウム塩（３）の添加量は、樹脂基材１重量部に対して、通常、０．０１～２５重量％、好ましくは１～１０重量％、特に好ましくは１～５重量％である。
The amount of diphosphonium salt (1) or diphosphonium salt (3) added to the resin composition is usually 0.01 to 25% by weight, preferably 1 to 10% by weight, based on 1 part by weight of the resin substrate. Particularly preferred is 1 to 5% by weight.
樹脂組成物には、樹脂および帯電防止剤以外に樹脂組成物の性質を損なわない範囲で、公知の添加剤を加えてもよい。添加剤としては、染料、顔料、補強剤、充填剤、可塑剤、酸化防止剤、難燃剤、紫外線吸収剤などが挙げられる。
In addition to the resin and the antistatic agent, known additives may be added to the resin composition as long as the properties of the resin composition are not impaired. Examples of the additive include dyes, pigments, reinforcing agents, fillers, plasticizers, antioxidants, flame retardants, and ultraviolet absorbers.
本発明の硬化促進剤は、エポキシ樹脂と硬化剤の硬化反応を促進させる化合物で、ジホスホニウム塩（１）またはジホスホニウム塩（３）を有効成分として含有するものである。それらは、単独であっても硬化促進剤として使用でき、必要に応じて安定化剤などの添加剤または溶媒などを混合してもよい。
The curing accelerator of the present invention is a compound that accelerates the curing reaction between the epoxy resin and the curing agent, and contains a diphosphonium salt (1) or a diphosphonium salt (3) as an active ingredient. They can be used alone or as curing accelerators, and may be mixed with additives such as stabilizers or solvents as necessary.
本発明の硬化促進剤の添加量は、エポキシ樹脂に対して、通常、０．０１～１５重量％、好ましくは０．０１～１０重量％、特に好ましくは１～５重量％である。
The addition amount of the curing accelerator of the present invention is usually from 0.01 to 15% by weight, preferably from 0.01 to 10% by weight, particularly preferably from 1 to 5% by weight, based on the epoxy resin.
つぎに、本発明を実施例に基づいて具体的に説明する。本発明はなんらこれらに限定されるものではない。下記の実施例中、１Ｈ－ＮＭＲは、日本電子データム株式会社製核磁気共鳴装置ＡＬ－４００を使用し、溶媒にＣＤＣｌ３またはＤＭＳＯを用い、４００ＭＨｚで測定した。表面抵抗率は、株式会社三菱化学アナリテック製ハイレスターＵＰ（ＭＣＰ―ＨＴ４５０）を使用し、印加電圧１０００Ｖ、２５℃±２℃、４５±５％ＲＨの条件で測定した。
Next, the present invention will be specifically described based on examples. The present invention is not limited to these. In the following examples, 1 H-NMR was measured at 400 MHz using a nuclear magnetic resonance apparatus AL-400 manufactured by JEOL Datum, using CDCl 3 or DMSO as a solvent. The surface resistivity was measured under the conditions of an applied voltage of 1000 V, 25 ° C. ± 2 ° C., and 45 ± 5% RH using Mitsubishi Chemical Analytech's Hiresta UP (MCP-HT450).
実施例１
ジブロモビフェニル７８．６９ｇ（０．２５ｍｏｌ）およびテトラヒドロフラン６２４．４５ｇの混合溶液を－７０℃に冷却し、その混合溶液に１．６ｍｏｌ／ｌ ｎ－ＢｕＬｉヘキサン溶液２６０．６３ｇ（０．６０ｍｏｌ）を滴下した。ｎ－ＢｕＬｉヘキサン溶液の滴下終了後、反応混合物を０℃に昇温して、さらに１時間反応し、再度－７０℃まで冷却した。その反応混合物にジフェニルクロロホスフィン１１２．２４ｇ（０．５１ｍｏｌ）を滴下した。ジフェニルクロロホスフィンの滴下終了後、反応混合物を０℃に昇温して、さらに１時間反応させた。この反応混合物にイオン交換水６２８．７８ｇを添加して、結晶を析出させた。この混合物をろ過し、結晶を得た。得られた結晶をイオン交換水およびメタノールで洗浄し、洗浄後の結晶を減圧下で乾燥して、１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニル９１．４７ｇ（収率６９．４１％）を得た。１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニルの１Ｈ－ＮＭＲおよび３１Ｐ－ＮＭＲを次に示す。 Example 1
A mixed solution of 78.69 g (0.25 mol) of dibromobiphenyl and 624.45 g of tetrahydrofuran was cooled to −70 ° C., and 260.63 g (0.60 mol) of a 1.6 mol / l n-BuLi hexane solution was added dropwise to the mixed solution. did. After completion of the dropwise addition of the n-BuLi hexane solution, the reaction mixture was heated to 0 ° C., reacted for another 1 hour, and cooled again to −70 ° C. To the reaction mixture, 112.24 g (0.51 mol) of diphenylchlorophosphine was added dropwise. After completion of the dropwise addition of diphenylchlorophosphine, the reaction mixture was heated to 0 ° C. and further reacted for 1 hour. To this reaction mixture, 628.78 g of ion-exchanged water was added to precipitate crystals. The mixture was filtered to obtain crystals. The obtained crystals were washed with ion-exchanged water and methanol, and the washed crystals were dried under reduced pressure to obtain 91.47 g of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl (yield 69). .41%). 1 H-NMR and 31 P-NMR of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl are shown below.
ジブロモビフェニル７８．６９ｇ（０．２５ｍｏｌ）およびテトラヒドロフラン６２４．４５ｇの混合溶液を－７０℃に冷却し、その混合溶液に１．６ｍｏｌ／ｌ ｎ－ＢｕＬｉヘキサン溶液２６０．６３ｇ（０．６０ｍｏｌ）を滴下した。ｎ－ＢｕＬｉヘキサン溶液の滴下終了後、反応混合物を０℃に昇温して、さらに１時間反応し、再度－７０℃まで冷却した。その反応混合物にジフェニルクロロホスフィン１１２．２４ｇ（０．５１ｍｏｌ）を滴下した。ジフェニルクロロホスフィンの滴下終了後、反応混合物を０℃に昇温して、さらに１時間反応させた。この反応混合物にイオン交換水６２８．７８ｇを添加して、結晶を析出させた。この混合物をろ過し、結晶を得た。得られた結晶をイオン交換水およびメタノールで洗浄し、洗浄後の結晶を減圧下で乾燥して、１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニル９１．４７ｇ（収率６９．４１％）を得た。１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニルの１Ｈ－ＮＭＲおよび３１Ｐ－ＮＭＲを次に示す。 Example 1
A mixed solution of 78.69 g (0.25 mol) of dibromobiphenyl and 624.45 g of tetrahydrofuran was cooled to −70 ° C., and 260.63 g (0.60 mol) of a 1.6 mol / l n-BuLi hexane solution was added dropwise to the mixed solution. did. After completion of the dropwise addition of the n-BuLi hexane solution, the reaction mixture was heated to 0 ° C., reacted for another 1 hour, and cooled again to −70 ° C. To the reaction mixture, 112.24 g (0.51 mol) of diphenylchlorophosphine was added dropwise. After completion of the dropwise addition of diphenylchlorophosphine, the reaction mixture was heated to 0 ° C. and further reacted for 1 hour. To this reaction mixture, 628.78 g of ion-exchanged water was added to precipitate crystals. The mixture was filtered to obtain crystals. The obtained crystals were washed with ion-exchanged water and methanol, and the washed crystals were dried under reduced pressure to obtain 91.47 g of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl (yield 69). .41%). 1 H-NMR and 31 P-NMR of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl are shown below.
１Ｈ－ＮＭＲ（ＣＤＣｌ３）δ：７．５０－７．６０（ｍ，４Ｈ）、７．３０－７．５５（ｍ，２４Ｈ），３１Ｐ－ＮＭＲ（ＣＤＣｌ３）δ：４．６３
1 H-NMR (CDCl 3 ) δ: 7.50-7.60 (m, 4H), 7.30-7.55 (m, 24H), 31 P-NMR (CDCl 3) δ: 4.63
実施例２
実施例１で得た１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニル９０．８２ｇ（０．１７ｍｏｌ）にブロモフェノール６６．２３ｇ（０．３８ｍｏｌ）、エチレングリコール６２２．５０ｇおよび塩化ニッケル六水和物９．５２ｇ（０．０３ｍｏｌ）を加えた混合物を、１７５℃で５時間反応させた。得られた反応混合物を室温まで冷却し、イオン交換水を加え、ジクロロメタンで抽出した。得られた有機層をイオン交換水で洗浄し、さらに減圧下で濃縮して濃縮物を得た。得られた濃縮物をジクロロメタン３３５．００ｇに溶解させてジクロロメタン溶液とした。得られたジクロロメタン溶液を、アセトニトリル８３９．７３ｇに、室温下、１．５時間かけて滴下した。得られた混合物を１時間撹拌し、結晶を析出させた。この混合物をろ過し、結晶を得た。得られた結晶をアセトニトリルで洗浄し、減圧下で乾燥して、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミド１２７．０９ｇ（収率８４．１８％）を得た。１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミドの１Ｈ－ＮＭＲ、および３１Ｐ－ＮＭＲを次に示す。 Example 2
90.82 g (0.17 mol) of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl obtained in Example 1 was mixed with 66.23 g (0.38 mol) of bromophenol, 622.50 g of ethylene glycol and chloride. The mixture to which 9.52 g (0.03 mol) of nickel hexahydrate was added was reacted at 175 ° C. for 5 hours. The resulting reaction mixture was cooled to room temperature, ion exchanged water was added, and the mixture was extracted with dichloromethane. The obtained organic layer was washed with ion-exchanged water and further concentrated under reduced pressure to obtain a concentrate. The obtained concentrate was dissolved in 335.00 g of dichloromethane to obtain a dichloromethane solution. The obtained dichloromethane solution was added dropwise to 839.73 g of acetonitrile at room temperature over 1.5 hours. The obtained mixture was stirred for 1 hour to precipitate crystals. The mixture was filtered to obtain crystals. The obtained crystals were washed with acetonitrile and dried under reduced pressure to give 127.09 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide (yield 84.18%). ) 1 H-NMR and 31 P-NMR of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide are shown below.
実施例１で得た１，１’－ビス（ジフェニルホスフィン）－４，４’－ビフェニル９０．８２ｇ（０．１７ｍｏｌ）にブロモフェノール６６．２３ｇ（０．３８ｍｏｌ）、エチレングリコール６２２．５０ｇおよび塩化ニッケル六水和物９．５２ｇ（０．０３ｍｏｌ）を加えた混合物を、１７５℃で５時間反応させた。得られた反応混合物を室温まで冷却し、イオン交換水を加え、ジクロロメタンで抽出した。得られた有機層をイオン交換水で洗浄し、さらに減圧下で濃縮して濃縮物を得た。得られた濃縮物をジクロロメタン３３５．００ｇに溶解させてジクロロメタン溶液とした。得られたジクロロメタン溶液を、アセトニトリル８３９．７３ｇに、室温下、１．５時間かけて滴下した。得られた混合物を１時間撹拌し、結晶を析出させた。この混合物をろ過し、結晶を得た。得られた結晶をアセトニトリルで洗浄し、減圧下で乾燥して、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミド１２７．０９ｇ（収率８４．１８％）を得た。１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミドの１Ｈ－ＮＭＲ、および３１Ｐ－ＮＭＲを次に示す。 Example 2
90.82 g (0.17 mol) of 1,1′-bis (diphenylphosphine) -4,4′-biphenyl obtained in Example 1 was mixed with 66.23 g (0.38 mol) of bromophenol, 622.50 g of ethylene glycol and chloride. The mixture to which 9.52 g (0.03 mol) of nickel hexahydrate was added was reacted at 175 ° C. for 5 hours. The resulting reaction mixture was cooled to room temperature, ion exchanged water was added, and the mixture was extracted with dichloromethane. The obtained organic layer was washed with ion-exchanged water and further concentrated under reduced pressure to obtain a concentrate. The obtained concentrate was dissolved in 335.00 g of dichloromethane to obtain a dichloromethane solution. The obtained dichloromethane solution was added dropwise to 839.73 g of acetonitrile at room temperature over 1.5 hours. The obtained mixture was stirred for 1 hour to precipitate crystals. The mixture was filtered to obtain crystals. The obtained crystals were washed with acetonitrile and dried under reduced pressure to give 127.09 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide (yield 84.18%). ) 1 H-NMR and 31 P-NMR of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide are shown below.
１Ｈ－ＮＭＲ（ＤＭＳＯ）δ：１０．５０－１２．００（ｂｒ，１Ｈ）、８．１７－８．２０（ｍ，２Ｈ）、７．９０－８．００（ｍ，２Ｈ）、７．７０－７．９０（ｍ，１０Ｈ）、７．５０－７．６０（ｍ，２Ｈ）、７．１５－７．２０（ｍ，２Ｈ），３１Ｐ－ＮＭＲ（ＤＭＳＯ）δ：２２．８８
1 H-NMR (DMSO) δ: 10.50-12.00 (br, 1H), 8.17-8.20 (m, 2H), 7.90-8.00 (m, 2H), 7. 70-7.90 (m, 10H), 7.50-7.60 (m, 2H), 7.15-7.20 (m, 2H), 31 P-NMR (DMSO) δ: 22.88
実施例３
実施例２で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミド５００．７０ｇ（０．５８ｍｏｌ）に、７６．１％ビス（トリフルオロメタンスルホニル）イミド酸リチウム水溶液４５７．７４ｇ（１．２１ｍｏｌ）、ジクロロメタン２０１２．４５ｇおよびイオン交換水８９０．６６ｇを加えて、室温で３時間反応させた。この反応混合物をイオン交換水で２回洗浄した後、有機層を減圧下で濃縮して、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド６２１．８３ｇ（収率８４．９９％）を得た。１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの１Ｈ－ＮＭＲ、および３１Ｐ－ＮＭＲを次に示す。 Example 3
76.1% bis (trifluoromethanesulfonyl) imide was added to 500.70 g (0.58 mol) of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide obtained in Example 2. 457.74 g (1.21 mol) of a lithium acid aqueous solution, 2012.45 g of dichloromethane and 890.66 g of ion-exchanged water were added, and the mixture was reacted at room temperature for 3 hours. The reaction mixture was washed twice with ion exchanged water, and then the organic layer was concentrated under reduced pressure to obtain 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethane). This gave 621.83 g (yield 84.99%) of sulfonyl) imide. 1 H-NMR and 31 P-NMR of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide are shown below.
実施例２で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ブロミド５００．７０ｇ（０．５８ｍｏｌ）に、７６．１％ビス（トリフルオロメタンスルホニル）イミド酸リチウム水溶液４５７．７４ｇ（１．２１ｍｏｌ）、ジクロロメタン２０１２．４５ｇおよびイオン交換水８９０．６６ｇを加えて、室温で３時間反応させた。この反応混合物をイオン交換水で２回洗浄した後、有機層を減圧下で濃縮して、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド６２１．８３ｇ（収率８４．９９％）を得た。１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの１Ｈ－ＮＭＲ、および３１Ｐ－ＮＭＲを次に示す。 Example 3
76.1% bis (trifluoromethanesulfonyl) imide was added to 500.70 g (0.58 mol) of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bromide obtained in Example 2. 457.74 g (1.21 mol) of a lithium acid aqueous solution, 2012.45 g of dichloromethane and 890.66 g of ion-exchanged water were added, and the mixture was reacted at room temperature for 3 hours. The reaction mixture was washed twice with ion exchanged water, and then the organic layer was concentrated under reduced pressure to obtain 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethane). This gave 621.83 g (yield 84.99%) of sulfonyl) imide. 1 H-NMR and 31 P-NMR of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide are shown below.
１Ｈ－ＮＭＲ（ＤＭＳＯ）δ：１０．５０－１２．００（ｂｒ，１Ｈ）、８．１７－８．２０（ｍ，２Ｈ）、７．９０－８．００（ｍ，２Ｈ）、７．７０－７．９０（ｍ，１０Ｈ）、７．５０－７．６０（ｍ，２Ｈ）、７．１５－７．２０（ｍ，２Ｈ），３１Ｐ－ＮＭＲ（ＤＭＳＯ）δ：２２．８８
1 H-NMR (DMSO) δ: 10.50-12.00 (br, 1H), 8.17-8.20 (m, 2H), 7.90-8.00 (m, 2H), 7. 70-7.90 (m, 10H), 7.50-7.60 (m, 2H), 7.15-7.20 (m, 2H), 31 P-NMR (DMSO) δ: 22.88
実施例４
エポキシ樹脂（三菱化学株式会社製、ｊＥＲ８２８、エポキシ当量１９０）４．４ｇを試験管に入れ、そこに３，３’－イミノビスプロピルアミン０．６ｇおよび実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド０．２５ｇを添加して、１分間ガラス棒で撹拌した。この混合物を７０℃の油浴で加熱しながら撹拌し、硬化までの時間を測定した。硬化時間は、イミノビスプロピルアミンおよび１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを添加後に加熱を開始してから、樹脂の硬化により撹拌が不可能となるまでの時間（秒）とした。その結果を表１に示す。 Example 4
4.4 g of an epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER828, epoxy equivalent 190) was put in a test tube, and 0.6 g of 3,3′-iminobispropylamine and 1,1′- obtained in Example 3 were added thereto. 0.25 g of bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was added and stirred with a glass rod for 1 minute. The mixture was stirred while being heated in a 70 ° C. oil bath, and the time until curing was measured. Curing time was determined by adding heating after the addition of iminobispropylamine and 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, The time (seconds) until stirring became impossible by curing was set. The results are shown in Table 1.
エポキシ樹脂（三菱化学株式会社製、ｊＥＲ８２８、エポキシ当量１９０）４．４ｇを試験管に入れ、そこに３，３’－イミノビスプロピルアミン０．６ｇおよび実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミド０．２５ｇを添加して、１分間ガラス棒で撹拌した。この混合物を７０℃の油浴で加熱しながら撹拌し、硬化までの時間を測定した。硬化時間は、イミノビスプロピルアミンおよび１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを添加後に加熱を開始してから、樹脂の硬化により撹拌が不可能となるまでの時間（秒）とした。その結果を表１に示す。 Example 4
4.4 g of an epoxy resin (manufactured by Mitsubishi Chemical Corporation, jER828, epoxy equivalent 190) was put in a test tube, and 0.6 g of 3,3′-iminobispropylamine and 1,1′- obtained in Example 3 were added thereto. 0.25 g of bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was added and stirred with a glass rod for 1 minute. The mixture was stirred while being heated in a 70 ° C. oil bath, and the time until curing was measured. Curing time was determined by adding heating after the addition of iminobispropylamine and 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl bis (trifluoromethanesulfonyl) imide, The time (seconds) until stirring became impossible by curing was set. The results are shown in Table 1.
比較例１
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 1
In Example 4, the curing time was measured in the same manner as in Example 4 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. did. The results are shown in Table 1.
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 1
In Example 4, the curing time was measured in the same manner as in Example 4 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. did. The results are shown in Table 1.
比較例２
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの代わりにテトラフェニルホスホニウム＝ビス（トリフルオロメタンスルホニル）イミドを用いた以外は、実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 2
In Example 4, tetraphenylphosphonium bis (trifluoromethanesulfonyl) imide was used instead of 1,1'-bis (4-hydroxyphenyldiphenylphosphonium) -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide. The curing time was measured in the same manner as in Example 4 except that. The results are shown in Table 1.
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの代わりにテトラフェニルホスホニウム＝ビス（トリフルオロメタンスルホニル）イミドを用いた以外は、実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 2
In Example 4, tetraphenylphosphonium bis (trifluoromethanesulfonyl) imide was used instead of 1,1'-bis (4-hydroxyphenyldiphenylphosphonium) -4,4'-biphenyl bis (trifluoromethanesulfonyl) imide. The curing time was measured in the same manner as in Example 4 except that. The results are shown in Table 1.
比較例３
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの代わりにトリフェニルホスフィンを用いた以外は、実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 3
Example 4 is the same as Example 4 except that triphenylphosphine was used instead of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide. Similarly, the curing time was measured. The results are shown in Table 1.
実施例４において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドの代わりにトリフェニルホスフィンを用いた以外は、実施例４と同様にして硬化時間を測定した。その結果を表１に示す。 Comparative Example 3
Example 4 is the same as Example 4 except that triphenylphosphine was used instead of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide. Similarly, the curing time was measured. The results are shown in Table 1.
表１の結果から本発明のジホスホニウム塩は、エポキシ樹脂の硬化促進剤として優れていることが示された。
From the results of Table 1, it was shown that the diphosphonium salt of the present invention is excellent as an epoxy resin curing accelerator.
実施例５
ポリカーボネート樹脂（住友ダウ株式会社製、カリバー（商標）２００－１３ ＮＡＴ）３．２ｇとジクロロメタン２０ｍＬを混合し、ポリカーボネート樹脂のジクロロメタン溶液を調製した。その溶液に、実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを０．１６ｇ添加し、溶解させた。得られた溶液を金型（１２ｃｍ×２０ｃｍ×２ｃｍ）に流し込み、これを室温で１時間乾燥した。さらに、４０℃で１時間乾燥することにより、ポリカーボネート樹脂シートを作成した。得られたポリカーボネート樹脂シートの表面抵抗率を測定した。その結果を表２に示す。 Example 5
3.2 g of polycarbonate resin (manufactured by Sumitomo Dow Co., Ltd., Caliber (trademark) 200-13 NAT) and 20 mL of dichloromethane were mixed to prepare a dichloromethane solution of the polycarbonate resin. To the solution, 0.16 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide obtained in Example 3 was added and dissolved. The obtained solution was poured into a mold (12 cm × 20 cm × 2 cm) and dried at room temperature for 1 hour. Furthermore, the polycarbonate resin sheet was created by drying at 40 degreeC for 1 hour. The surface resistivity of the obtained polycarbonate resin sheet was measured. The results are shown in Table 2.
ポリカーボネート樹脂（住友ダウ株式会社製、カリバー（商標）２００－１３ ＮＡＴ）３．２ｇとジクロロメタン２０ｍＬを混合し、ポリカーボネート樹脂のジクロロメタン溶液を調製した。その溶液に、実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを０．１６ｇ添加し、溶解させた。得られた溶液を金型（１２ｃｍ×２０ｃｍ×２ｃｍ）に流し込み、これを室温で１時間乾燥した。さらに、４０℃で１時間乾燥することにより、ポリカーボネート樹脂シートを作成した。得られたポリカーボネート樹脂シートの表面抵抗率を測定した。その結果を表２に示す。 Example 5
3.2 g of polycarbonate resin (manufactured by Sumitomo Dow Co., Ltd., Caliber (trademark) 200-13 NAT) and 20 mL of dichloromethane were mixed to prepare a dichloromethane solution of the polycarbonate resin. To the solution, 0.16 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide obtained in Example 3 was added and dissolved. The obtained solution was poured into a mold (12 cm × 20 cm × 2 cm) and dried at room temperature for 1 hour. Furthermore, the polycarbonate resin sheet was created by drying at 40 degreeC for 1 hour. The surface resistivity of the obtained polycarbonate resin sheet was measured. The results are shown in Table 2.
比較例４
実施例５において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は、実施例５と同様にしてポリカーボネート樹脂シートを作成した。得られたポリカーボネート樹脂シートの表面抵抗率を測定した。その結果を表２に示す。 Comparative Example 4
A polycarbonate resin sheet was prepared in the same manner as in Example 5 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. It was created. The surface resistivity of the obtained polycarbonate resin sheet was measured. The results are shown in Table 2.
実施例５において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は、実施例５と同様にしてポリカーボネート樹脂シートを作成した。得られたポリカーボネート樹脂シートの表面抵抗率を測定した。その結果を表２に示す。 Comparative Example 4
A polycarbonate resin sheet was prepared in the same manner as in Example 5 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. It was created. The surface resistivity of the obtained polycarbonate resin sheet was measured. The results are shown in Table 2.
実施例６
ポリビニルブチラール（ＰＶＢ）樹脂（分子量２４００、和光純薬工業株式会社製）３．２ｇとジクロロメタン：アセトン＝８：１（重量比）の混合溶媒４５ｍＬとを混合し、ポリビニルブチラール樹脂溶液を調製した。この溶液に、実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを０．１６ｇ添加し、溶解させた。得られた溶液を金型（１２ｃｍ×２０ｃｍ×２ｃｍ）に流し込み、これを室温で１時間乾燥した。さらに４０℃で１時間乾燥して、ポリビニルブチラール樹脂シートを作成した。得られたポリビニルブチラール樹脂シートの表面抵抗率を測定した。その結果を表３に示す。 Example 6
Polyvinyl butyral (PVB) resin (molecular weight 2400, manufactured by Wako Pure Chemical Industries, Ltd.) 3.2 g and dichloromethane: acetone = 8: 1 (weight ratio) mixed solvent 45 mL were mixed to prepare a polyvinyl butyral resin solution. To this solution, 0.16 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide obtained in Example 3 was added and dissolved. The obtained solution was poured into a mold (12 cm × 20 cm × 2 cm) and dried at room temperature for 1 hour. Furthermore, it dried at 40 degreeC for 1 hour, and the polyvinyl butyral resin sheet was created. The surface resistivity of the obtained polyvinyl butyral resin sheet was measured. The results are shown in Table 3.
ポリビニルブチラール（ＰＶＢ）樹脂（分子量２４００、和光純薬工業株式会社製）３．２ｇとジクロロメタン：アセトン＝８：１（重量比）の混合溶媒４５ｍＬとを混合し、ポリビニルブチラール樹脂溶液を調製した。この溶液に、実施例３で得た１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを０．１６ｇ添加し、溶解させた。得られた溶液を金型（１２ｃｍ×２０ｃｍ×２ｃｍ）に流し込み、これを室温で１時間乾燥した。さらに４０℃で１時間乾燥して、ポリビニルブチラール樹脂シートを作成した。得られたポリビニルブチラール樹脂シートの表面抵抗率を測定した。その結果を表３に示す。 Example 6
Polyvinyl butyral (PVB) resin (molecular weight 2400, manufactured by Wako Pure Chemical Industries, Ltd.) 3.2 g and dichloromethane: acetone = 8: 1 (weight ratio) mixed solvent 45 mL were mixed to prepare a polyvinyl butyral resin solution. To this solution, 0.16 g of 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide obtained in Example 3 was added and dissolved. The obtained solution was poured into a mold (12 cm × 20 cm × 2 cm) and dried at room temperature for 1 hour. Furthermore, it dried at 40 degreeC for 1 hour, and the polyvinyl butyral resin sheet was created. The surface resistivity of the obtained polyvinyl butyral resin sheet was measured. The results are shown in Table 3.
比較例５
実施例６において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は、実施例６と同様にしてポリビニルブチラール樹脂シートを作成した。得られたポリビニルブチラール樹脂シートの表面抵抗率を測定した。その結果を表３に示す。 Comparative Example 5
A polyvinyl butyral resin was prepared in the same manner as in Example 6 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. Created a sheet. The surface resistivity of the obtained polyvinyl butyral resin sheet was measured. The results are shown in Table 3.
実施例６において、１，１’－ビス（４－ヒドロキシフェニルジフェニルホスホニウム）－４，４’－ビフェニル＝ビス（トリフルオロメタンスルホニル）イミドを用いない以外は、実施例６と同様にしてポリビニルブチラール樹脂シートを作成した。得られたポリビニルブチラール樹脂シートの表面抵抗率を測定した。その結果を表３に示す。 Comparative Example 5
A polyvinyl butyral resin was prepared in the same manner as in Example 6 except that 1,1′-bis (4-hydroxyphenyldiphenylphosphonium) -4,4′-biphenyl = bis (trifluoromethanesulfonyl) imide was not used. Created a sheet. The surface resistivity of the obtained polyvinyl butyral resin sheet was measured. The results are shown in Table 3.
Claims (8)
- 式（１）：
- 式（３）：
- Ｒ１およびＲ２が、フェニル基である請求項１または２に記載のジホスホニウム塩。 The diphosphonium salt according to claim 1 or 2, wherein R 1 and R 2 are phenyl groups.
- ｎが、２である請求項１または２に記載のジホスホニウム塩。 The diphosphonium salt according to claim 1 or 2, wherein n is 2.
- 下記第１反応工程と第２反応工程からなることを特徴とする、請求項２に記載のジホスホニウム塩の製造方法。
有機リチウム化合物の存在下、式（４）：
式（５）：
Ｘ－Ｙ－Ｘ （５）
（式中、ＹおよびＸは前記に同じ。）で表されるアリールジハライドを反応させて、式（６）：
第１反応工程により得られたジホスフィンをニッケル化合物の存在下で、式（７）：
In the presence of an organolithium compound, formula (4):
XYX (5)
(Wherein Y and X are the same as defined above) are reacted with an aryl dihalide represented by formula (6):
In the presence of a nickel compound, diphosphine obtained by the first reaction step is represented by the formula (7):
- 下記第３反応工程からなることを特徴とする請求項１に記載のジホスホニウム塩の製造方法。
請求項５で得られたジホスホニウム塩を、式（８）：
Ｍ＋・Ａ－ （８）
（式中、Ｍ＋は水素イオンまたはアルカリ金属イオンを示す。Ａ－は前記と同じ。）で表される化合物と反応させる第３反応工程。 It consists of the following 3rd reaction process, The manufacturing method of the diphosphonium salt of Claim 1 characterized by the above-mentioned.
The diphosphonium salt obtained in claim 5 is represented by the formula (8):
M +・ A − (8)
(Wherein M + represents a hydrogen ion or an alkali metal ion, A − is the same as defined above), and a third reaction step. - 請求項１または２に記載のジホスホニウム塩を少なくとも１種含有することを特徴とする帯電防止剤。 An antistatic agent comprising at least one diphosphonium salt according to claim 1 or 2.
- 請求項１または２に記載のジホスホニウム塩を少なくとも１種含有することを特徴とする硬化促進剤。 A curing accelerator comprising at least one diphosphonium salt according to claim 1 or 2.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020147023107A KR102077448B1 (en) | 2012-07-02 | 2013-06-17 | Novel diphosphonium salt and method for producing same |
| JP2014523570A JP6182138B2 (en) | 2012-07-02 | 2013-06-17 | Novel diphosphonium salt and process for producing the same |
| CN201380011634.0A CN104144937B (en) | 2012-07-02 | 2013-06-17 | Diphosphonium salt and method for producing same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012-148145 | 2012-07-02 | ||
| JP2012148145 | 2012-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014006828A1 true WO2014006828A1 (en) | 2014-01-09 |
Family
ID=49881604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2013/003774 WO2014006828A1 (en) | 2012-07-02 | 2013-06-17 | Novel diphosphonium salt and method for producing same |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP6182138B2 (en) |
| KR (1) | KR102077448B1 (en) |
| CN (1) | CN104144937B (en) |
| WO (1) | WO2014006828A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114805437A (en) * | 2022-06-01 | 2022-07-29 | 山东科兴化工有限责任公司 | Oilfield sewage bactericide and preparation method thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680681A (en) * | 1992-07-15 | 1994-03-22 | Nippon Kayaku Co Ltd | Phosphonium compound and electrophotographic toner using the same |
| JPH0770361A (en) * | 1993-09-06 | 1995-03-14 | Nippon Chem Ind Co Ltd | Antistatic agent |
| JP2004182956A (en) * | 2002-12-06 | 2004-07-02 | Nichia Chem Ind Ltd | Epoxy resin composition |
| JP2005232385A (en) * | 2004-02-20 | 2005-09-02 | Sumitomo Bakelite Co Ltd | Hardening accelerator, epoxy resin composition and semiconductor device |
| JP2009029857A (en) * | 2007-07-25 | 2009-02-12 | Toyo Ink Mfg Co Ltd | Antistatic agent and use thereof |
| JP2011132299A (en) * | 2009-12-22 | 2011-07-07 | Shin-Etsu Chemical Co Ltd | Silicone resin composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08198921A (en) | 1995-01-25 | 1996-08-06 | Maruzen Petrochem Co Ltd | Thermosetting resin composition |
| US6592988B1 (en) * | 1999-12-29 | 2003-07-15 | 3M Innovative Properties Company | Water-and oil-repellent, antistatic composition |
-
2013
- 2013-06-17 WO PCT/JP2013/003774 patent/WO2014006828A1/en active Application Filing
- 2013-06-17 CN CN201380011634.0A patent/CN104144937B/en active Active
- 2013-06-17 JP JP2014523570A patent/JP6182138B2/en active Active
- 2013-06-17 KR KR1020147023107A patent/KR102077448B1/en active IP Right Grant
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680681A (en) * | 1992-07-15 | 1994-03-22 | Nippon Kayaku Co Ltd | Phosphonium compound and electrophotographic toner using the same |
| JPH0770361A (en) * | 1993-09-06 | 1995-03-14 | Nippon Chem Ind Co Ltd | Antistatic agent |
| JP2004182956A (en) * | 2002-12-06 | 2004-07-02 | Nichia Chem Ind Ltd | Epoxy resin composition |
| JP2005232385A (en) * | 2004-02-20 | 2005-09-02 | Sumitomo Bakelite Co Ltd | Hardening accelerator, epoxy resin composition and semiconductor device |
| JP2009029857A (en) * | 2007-07-25 | 2009-02-12 | Toyo Ink Mfg Co Ltd | Antistatic agent and use thereof |
| JP2011132299A (en) * | 2009-12-22 | 2011-07-07 | Shin-Etsu Chemical Co Ltd | Silicone resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104144937A (en) | 2014-11-12 |
| JP6182138B2 (en) | 2017-08-16 |
| CN104144937B (en) | 2017-04-26 |
| JPWO2014006828A1 (en) | 2016-06-02 |
| KR102077448B1 (en) | 2020-02-14 |
| KR20150027030A (en) | 2015-03-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103596965B (en) | There is the salt of trialkoxysilylalkyl | |
| JP3592405B2 (en) | Method for producing sulfur-containing organosilicon compound | |
| US9701700B2 (en) | Process for the preparation of acylphosphanes | |
| CA2839203C (en) | Ionic liquid | |
| JP2008222592A (en) | New phosphonium salt ionic liquid and reaction solvent using the same | |
| JP5559322B2 (en) | Hydroxyphenylphosphine oxide mixtures and their use as flame retardants for epoxy resins | |
| JPS632972B2 (en) | ||
| EP2998335B1 (en) | Method for producing biphenyl-skeleton-containing epoxy resin | |
| JP6182138B2 (en) | Novel diphosphonium salt and process for producing the same | |
| WO2017090346A1 (en) | Silicon-containing sulfonate | |
| KR102098726B1 (en) | Ionic liquid | |
| Arhangelskis et al. | Influence of ligand composition on crystal structure formation–isostructurality and morphotropism | |
| CN105295092A (en) | Cyclopentadienyl iron salt flame retardant containing phosphorus and nitrogen elements, and preparation method and application thereof | |
| JP2004262896A (en) | Quaternary ammonium room temperature molten salt and method for producing the same | |
| JP6399555B2 (en) | A method for producing polyaniline having a self-doping function and an antistatic agent comprising polyaniline produced by the method. | |
| WO2022025050A1 (en) | Method for producing ammonia | |
| JP6228862B2 (en) | Process for producing ionic compounds | |
| JP2013063949A (en) | Onium salt, and antistatic containing the same | |
| JP2005145924A (en) | Quaternary ammonium salt | |
| JPS6225705B2 (en) | ||
| US3426073A (en) | Mesomeric phosphonium salts | |
| JP2005203363A (en) | Normal temperature fused salt and its manufacturing method | |
| JP2013184931A (en) | Method for producing poly-substituted amine | |
| KR20190134796A (en) | Method for preparing cationic silicon (II) compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13812875 Country of ref document: EP Kind code of ref document: A1 |
|
| ENP | Entry into the national phase |
Ref document number: 2014523570 Country of ref document: JP Kind code of ref document: A |
|
| ENP | Entry into the national phase |
Ref document number: 20147023107 Country of ref document: KR Kind code of ref document: A |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 13812875 Country of ref document: EP Kind code of ref document: A1 |