WO2009136482A1 - スルホニウム塩、光酸発生剤、光硬化性組成物及びこの硬化体 - Google Patents
スルホニウム塩、光酸発生剤、光硬化性組成物及びこの硬化体 Download PDFInfo
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- WO2009136482A1 WO2009136482A1 PCT/JP2009/001925 JP2009001925W WO2009136482A1 WO 2009136482 A1 WO2009136482 A1 WO 2009136482A1 JP 2009001925 W JP2009001925 W JP 2009001925W WO 2009136482 A1 WO2009136482 A1 WO 2009136482A1
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- Prior art keywords
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- atom
- carbon atoms
- phenyl
- parts
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- 239000000203 mixture Substances 0.000 title claims description 43
- 150000004714 phosphonium salts Chemical class 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 54
- 150000001450 anions Chemical class 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical group [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 8
- 230000036211 photosensitivity Effects 0.000 abstract description 8
- 238000010894 electron beam technology Methods 0.000 abstract description 7
- -1 n-octyl Chemical group 0.000 description 324
- 238000006243 chemical reaction Methods 0.000 description 60
- 239000007983 Tris buffer Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 34
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 33
- 238000010521 absorption reaction Methods 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 28
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 24
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
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- 239000011651 chromium Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 20
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- 238000003786 synthesis reaction Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 239000011591 potassium Substances 0.000 description 17
- 229910052700 potassium Inorganic materials 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000004611 spectroscopical analysis Methods 0.000 description 14
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 9
- 239000002216 antistatic agent Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 239000007870 radical polymerization initiator Substances 0.000 description 9
- 239000003566 sealing material Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 239000002518 antifoaming agent Substances 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 8
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
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- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 description 6
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 5
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
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- 239000004593 Epoxy Substances 0.000 description 5
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
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- 125000001309 chloro group Chemical group Cl* 0.000 description 5
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
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- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000005649 metathesis reaction Methods 0.000 description 1
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
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- KEPMBNBMFNHEJO-UHFFFAOYSA-N methyl-octadecyl-phenacylsulfanium Chemical compound CCCCCCCCCCCCCCCCCC[S+](C)CC(=O)C1=CC=CC=C1 KEPMBNBMFNHEJO-UHFFFAOYSA-N 0.000 description 1
- NAYLGVYVQMVNFY-UHFFFAOYSA-N methyl-tri(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C(C)C)C(C)C NAYLGVYVQMVNFY-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
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- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- RSIZHSFCPFZAJC-UHFFFAOYSA-N naphthalen-1-yl(diphenyl)sulfanium Chemical compound C1=CC=CC=C1[S+](C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 RSIZHSFCPFZAJC-UHFFFAOYSA-N 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
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- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
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- 239000012860 organic pigment Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 239000012071 phase Substances 0.000 description 1
- NKIFVPLJBNCZFN-UHFFFAOYSA-N phenacyl(diphenyl)sulfanium Chemical compound C=1C=CC=CC=1C(=O)C[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NKIFVPLJBNCZFN-UHFFFAOYSA-N 0.000 description 1
- CBQRJWBLUBDHAZ-UHFFFAOYSA-N phenacyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1C(=O)C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CBQRJWBLUBDHAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
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- UZRUZACOSHWLOC-UHFFFAOYSA-M phenoxyaluminum Chemical compound [Al]OC1=CC=CC=C1 UZRUZACOSHWLOC-UHFFFAOYSA-M 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FFUQCRZBKUBHQT-UHFFFAOYSA-N phosphoryl fluoride Chemical compound FP(F)(F)=O FFUQCRZBKUBHQT-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
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- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 239000012266 salt solution Substances 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- RBNIOMQKAIDJGV-UHFFFAOYSA-N tert-butyl(2,3-dimethylbutan-2-yl)diazene Chemical compound CC(C)C(C)(C)N=NC(C)(C)C RBNIOMQKAIDJGV-UHFFFAOYSA-N 0.000 description 1
- SPJZSTLXABSXII-UHFFFAOYSA-N tert-butyl(trimethyl)azanium Chemical compound CC(C)(C)[N+](C)(C)C SPJZSTLXABSXII-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- AGWJLDNNUJKAHP-UHFFFAOYSA-N tetrahexylphosphanium Chemical compound CCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC AGWJLDNNUJKAHP-UHFFFAOYSA-N 0.000 description 1
- QQFYJXKKHBDLQV-UHFFFAOYSA-N tetrakis(2-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC=C1[P+](C=1C(=CC=CC=1)OC)(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC QQFYJXKKHBDLQV-UHFFFAOYSA-N 0.000 description 1
- XLZOKVSFMDOMTL-UHFFFAOYSA-N tetrakis(3-methoxyphenyl)phosphanium Chemical compound COC1=CC=CC([P+](C=2C=C(OC)C=CC=2)(C=2C=C(OC)C=CC=2)C=2C=C(OC)C=CC=2)=C1 XLZOKVSFMDOMTL-UHFFFAOYSA-N 0.000 description 1
- BFADQASMYNGYBX-UHFFFAOYSA-N tetrakis(4-methoxyphenyl)phosphanium Chemical compound C1=CC(OC)=CC=C1[P+](C=1C=CC(OC)=CC=1)(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFADQASMYNGYBX-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- CZMCQLHUFVDMLM-UHFFFAOYSA-N triethyl(phenacyl)phosphanium Chemical compound CC[P+](CC)(CC)CC(=O)C1=CC=CC=C1 CZMCQLHUFVDMLM-UHFFFAOYSA-N 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- COOSQAXLLKTSQO-UHFFFAOYSA-N trimethyl(2-methylpropyl)azanium Chemical compound CC(C)C[N+](C)(C)C COOSQAXLLKTSQO-UHFFFAOYSA-N 0.000 description 1
- BMTHNVMASXVELE-UHFFFAOYSA-N trimethyl(propan-2-yl)azanium Chemical compound CC(C)[N+](C)(C)C BMTHNVMASXVELE-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- VRRIVXLVXXAHJA-UHFFFAOYSA-N tris(2,3,4-tribromophenyl) phosphate Chemical compound BrC1=C(Br)C(Br)=CC=C1OP(=O)(OC=1C(=C(Br)C(Br)=CC=1)Br)OC1=CC=C(Br)C(Br)=C1Br VRRIVXLVXXAHJA-UHFFFAOYSA-N 0.000 description 1
- BINSXQFBKIIQJI-UHFFFAOYSA-N tris(4-hydroxyphenyl)sulfanium;chloride Chemical compound [Cl-].C1=CC(O)=CC=C1[S+](C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BINSXQFBKIIQJI-UHFFFAOYSA-N 0.000 description 1
- WUKMCKCDYKBLBG-UHFFFAOYSA-N tris(4-methoxyphenyl)sulfanium Chemical compound C1=CC(OC)=CC=C1[S+](C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WUKMCKCDYKBLBG-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
チオキサントン骨格をスルホニウム塩へ導入したスルホニウム塩(特許文献4)は、可視光の照射{特に、汎用高圧水銀灯のh線(405nm)、g線(436nm)や長波長のレーザー光}に対する光感応性が不十分であるという問題がある。
本発明の目的は、可視光、紫外線、電子線及びX線等の活性エネルギー線による十分な光感応性を有するスルホニウム塩を提供することである。
(式(1)中、R1は式(2)で表される基、R2及びR3はそれぞれ炭素数6~30のアリール基、炭素数4~30の複素環式炭化水素基、炭素数1~30のアルキル基、炭素数2~30のアルケニル基又は炭素数2~30のアルキニル基を表し、これらのアリール基、複素環式炭化水素基、アルキル基、アルケニル基又はアルキニル基の水素原子の一部が置換基(t)で置換されていてもよい。Sは硫黄原子、X-は一価の多原子アニオンを表す。)
(式(2)中、R4~R6はそれぞれアルキル基、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環式炭化水素基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ(ポリ)アルキレンオキシ基、アミノ基、シアノ基、ニトロ基又はハロゲン原子、k、m及びnはそれぞれR4、R5、R6の数を表し、kは0~4の整数、mは0~3の整数、nは0~4の整数であり、Aは-S-、-O-、-SO-、-SO2-又は-CO-で表される基、Oは酸素原子、Sは硫黄原子を表す。)
本発明の光酸発生剤は、上記のスルホニウム塩を含有するため、活性エネルギー線の作用によるカチオン重合性化合物の硬化性に優れる。本発明の光酸発生剤は、光感応性に優れたスルホニウム塩を含有するため、増感剤を用いなくても可視光でカチオン重合性化合物を硬化させることができる。
本発明のエネルギー線硬化性組成物は、上記の光酸発生剤を含有するため、可視光で硬化させることができる。本発明のエネルギー線硬化性組成物は、増感剤を用いる必要がないので、作業性に優れる。
本発明の硬化体は、増感剤が含まれないため、増感剤の残存による着色や劣化がない。
単環式アリール基としては、フェニル、ヒドロキシフェニル、トルイル、ジメチルフェニル、トリメチルフェニル、エチルフェニル、ジエチルフェニル、トリエチルフェニル、n-プロピルフェニル、イソプロピルフェニル、n-ブチルフェニル、イソブチルフェニル、sec-ブチルフェニル、tert-ブチルフェニル、メトキシフェニル、エトキシフェニル、n-プロポキシフェニル、イソプロポキシフェニル、n-ブトキシフェニル、イソブトキシフェニル、sec-ブトキシフェニル、tert-ブトキシフェニル、アセチルフェニル、ベンゾイルフェニル、ナフトイルフェニル、フェニルチオフェニル、ナフチルチオフェニル、ビフェニルイル、フェノキシフェニル、ナフトキシフェニル、ニトロフェニル、フルオロフェニル、クロロフェニル及びブロモフェニル等が挙げられる。
Yはハロゲン原子(フッ素原子が好ましい。)を表す。
aは4~6の整数を表す。
bは、1~5の整数が好ましく、さらに好ましくは2~4、特に好ましくは2又は3である。
cは、1~4の整数が好ましく、さらに好ましくは4である。
(HCO3 -、CH3CO3 -等)、アルミン酸イオン(AlCl4 -、AlF4 -等)、ヘキサフルオロビスマス酸イオン(BiF6 -)、カルボン酸イオン(CH3COO-、CF3COO-、C6H5COO-、CH3C6H4COO-、C6F5COO-、CF3C6H4COO-等)、アリールホウ酸イオン(B(C6H5)4 -、CH3CH2CH2CH2B(C6H5)3 -等)、チオシアン酸イオン(SCN-)及び硝酸イオン(NO3 -)等が使用できる。
次反応式で示される方法(たとえば、第4版実験化学講座24巻、1992年、丸善株式会社発行、376頁、特開平7-329399号公報、特開平8-165290号公報、特開平10-212286号公報又は特開平10-7680号公報(対応米国特許:第6,054,501;この文献に開示された開示内容を参照により本出願に取り込む。)等に記載されている方法)。
HXは、一価の多原子アニオンの共役酸を表す。HXとしては、入手しやすさ、酸の安定性及び反応収率の観点から、メタンスルホン酸、パーフルオロメタンスルホン酸及び硫酸が好ましい。
脱水剤は、たとえば、無水リン酸及び無水酢酸等を表す。
一価の多原子アニオン(X-)は、たとえば、上記のように副分解反応により、他の一価の多原子アニオン(X’-)に交換することができる。
MX’は、アルカリ金属(リチウム、ナトリウム及びカリウム等)カチオンと一価の多原子アニオン(MYa -、(Rf)bPF6-b -、R7 cBY4-c -、R7 cGaY4-c -、R8SO3 -、(R8SO2)3C-又は(R8SO2)2N-で表されるアニオンが好ましい。)との塩を表す。
MXは、アルカリ金属(リチウム、ナトリウム及びカリウム等)カチオンと一価の多原子アニオン(メタンスルホン酸アニオン、パーフルオロメタンスルホン酸アニオン及び硫酸水素アニオンが好ましい。)との塩を表す。
次反応式で示される方法(たとえば、Polymer Bulletin,14,279-286(1985)に記載されている方法;この文献に開示された開示内容を参照により本出願に取り込む。)。
Iは、ヨウ素原子を表す。
(C6H5CO2)2Cuは、安息香酸銅を表す。
反応温度は、100~130℃程度である。反応時間は、1~数十時間程度である。
反応終了後、反応液をエーテル等に注ぎ、析出した固体をろ別するか、または分離した油状物を有機溶媒で抽出して溶剤を除去することにより、本発明のスルホニウム塩が固体あるいは粘調な液体として得られる。
次反応式で示される方法(たとえば、特開平7-300504号公報に記載されている方法(対応米国特許:第5,798,396;この文献に開示された開示内容を参照により本出願に取り込む。)。
MXは、上記と同様である。
R3SO4 -は、有機硫酸アニオンを表す。
MR3SO4は、アルカリ金属カチオンと有機硫酸アニオンとの塩を表す。
第2段目の反応は、製造方法(1)と同様にして行うことができる。
次反応式で示される方法。
Hは、水素原子を表す。
H2SO4は硫酸を表す。
水の使用量(重量%)は、ジスルフィド(G6)の重量に基づいて、20000~40000程度が好ましく、さらに好ましくは25000~35000である。
Y1は、塩素原子又は臭素原子を表す。
Hは水素原子を表す。
塩基は、塩基(水酸化カリウム等)を表す。
Hは水素原子を表す。
酸化剤は、酸化剤(過酸化水素等)を表す。
Y1は、塩素原子又は臭素原子を表す。
Hは水素原子を表す。
塩基は、塩基(水酸化カリウム等)を表す。
次の反応式(4)のうち、第1段目の反応は、第4版実験化学講座19巻(1992年、丸善)424頁等に記載されている反応が適用できる。
また、第2段目の反応は、新実験化学講座14-II巻(1978年、丸善)804頁等に記載されている反応が適用できる。
Hは水素原子、Clは塩素原子、SO2Cl2は塩化スルフリルを表す。
ルイス酸は、AlCl3、SbCl5又はFeCl3で表される化合物等を表す。
SO2Cl2は塩化スルフリルを表す。
HS-R2は、チオールを表す。
HVは、強酸(たとえば、メタンスルホン酸、パーフルオロメタンスルホン酸及び硫酸等)を表す。
脱水剤は、たとえば、無水リン酸及び無水酢酸等を表す。
反応式中、R2、R3、R4、R5、R6、A、S、O、X-、k、m及びnは、式(1)及び(2)と同様である。
HXは、一価の多原子アニオンの共役酸を表す。HXとしては、入手しやすさ、酸の安定性及び反応収率の観点から、メタンスルホン酸、パーフルオロメタンスルホン酸及び硫酸が好ましい。
脱水剤は、たとえば、無水リン酸及び無水酢酸等を表す。
一価の多原子アニオン(X-)は、たとえば、上記のように副分解反応により、他の一価の多原子アニオン(X’-)に交換することができる。
MX’は、アルカリ金属(リチウム、ナトリウム及びカリウム等)カチオンと一価の多原子アニオン(MYa -、(Rf)bPF6-b -、R7 cBY4-c -、R7 cGaY4-c -、R8SO3 -、(R8SO2)3C-又は(R8SO2)2N-で表されるアニオンが好ましい。)との塩を表す。
MXは、アルカリ金属(リチウム、ナトリウム及びカリウム等)カチオンと一価の多原子アニオン(メタンスルホン酸アニオン、パーフルオロメタンスルホン酸アニオン及び硫酸アニオンが好ましい。)との塩を表す。
光酸発生剤とは、光照射によりその化学構造が分解し、酸を発生するものをいう。発生した酸は、エポキシドの硬化反応等の触媒として適用できる。
本発明の光酸発生剤は、単独で使用してもよいし、他の光酸発生剤を含有させてもよい。
エネルギー線としては、本発明のスルホニウム塩の分解を誘発するエネルギーを有する限りいかなるものでもよいが、低圧、中圧、高圧若しくは超高圧の水銀灯、メタルハライドランプ、LEDランプ、キセノンランプ、カーボンアークランプ、蛍光灯、半導体固体レーザ、アルゴンレーザ、He-Cdレーザ、KrFエキシマレーザ、ArFエキシマレーザ又はF2レーザ等から得られる紫外~可視光領域(波長:約100~約800nm)のエネルギー線が好ましい。なお、エネルギー線には、電子線又はX線等の高エネルギーを有する放射線を用いることもできる。
2-クロロチオキサントン11.0部、チオフェノール4.9部、水酸化カリウム2.5部及びN,N-ジメチルホルムアミド162部を均一混合し、130℃で9時間反応させた後、反応溶液を室温(約25℃)まで冷却し、蒸留水200部中に投入し、生成物を析出させた。これをろ過し、残渣を水で濾液のpHが中性になるまで洗浄した後、残渣を減圧乾燥させ、黄色粉末状の生成物を得た。カラムクロマトグラフィー(溶離液:トルエン/ヘキサン=1/1:容量比)にて生成物を精製して、2-(フェニルチオ)チオキサントンを収率45%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.43(1H、d)、8.25(1H、s)、7.75~7.90(3H、m)、7.66(1H、d)、7.60(1H、t)、7.42~7.46(5H、m)}。
製造例1で合成した2-(フェニルチオ)チオキサントン11.2部、アセトニトリル215部及び硫酸0.02部を40℃で撹拌しながら、これに30%過酸化水素水溶液4.0部を徐々に滴下し、40~45℃で14時間反応させた後、反応溶液を室温(約25℃)まで冷却し、蒸留水200部中に投入し、生成物を析出させた。これをろ過し、残渣を水で濾液のpHが中性になるまで洗浄した後、残渣を減圧乾燥させ、黄色粉末状の生成物を得た。カラムクロマトグラフィー(溶離液:酢酸エチル/トルエン=1/3:容量比)にて生成物を精製して、2-[(フェニル)スルフィニル]チオキサントンを収率83%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.75(1H、s)、8.45(1H、d)、8.01(2H、d)、7.75~7.85(4H、m)、7.53~7.62(4H、m)}。
製造例1で合成した2-(フェニルチオ)チオキサントン4.3部、製造例2で合成した2-[(フェニル)スルフィニル]チオキサントン4.5部、無水酢酸4.1部及びアセトニトリル110部を40℃で撹拌しながら、これにトリフルオロメタンスルホン酸2.4部を徐々に滴下し、40~45℃で1時間反応させた後、反応溶液を室温(約25℃)まで冷却し、蒸留水150部中に投入し、クロロホルムで抽出し、水相のpHが中性になるまで水で洗浄した。クロロホルム相をロータリーエバポレーターに移して溶媒を留去した後、トルエン50部を加えて超音波洗浄器でトルエン中に分散し約15分間静置してから上澄みを除く操作を3回繰り返して、生成した固体を洗浄した。ついで、固体をロータリーエバポレーターに移して、溶媒を留去することにより、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム トリフレート(トリフレート=トリフルオロメタンスルホン酸アニオン)を得た。このトリフレートをジクロロメタン212部に溶かし、10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液65部中に投入してから、室温(約25℃)で2時間撹拌し、ジクロロメタン層を分液操作にて水で3回洗浄した後、ロータリーエバポレーターに移して溶媒を留去することにより、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを収率95%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)}。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
製造例1で合成した2-(フェニルチオ)チオキサントン10.0部、ジフェニルスルホキシド6.3部、無水酢酸9.6部及びアセトニトリル273部を40℃で撹拌しながら、これにトリフルオロメタンスルホン酸5.7部を徐々に滴下し、40~45℃で3時間反応させた後、反応溶液を室温(約25℃)まで冷却し、蒸留水300部中に投入し、生成物を析出させた。これをろ過し、残渣を水で濾液のpHが中性になるまで洗浄し、残渣を減圧乾燥した後、ジエチルエーテル100部を加えて超音波洗浄器でジエチルエーテル中に分散し約15分間静置してから上澄みを除く操作を3回繰り返して、生成した固体を洗浄し、ロータリーエバポレーターで溶媒を留去することにより、黄色粉末状固体を得た。黄色粉末状固体をジクロロメタン200部に溶かし、10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液103部中に投入した後、室温(約25℃)で2時間撹拌し、有機層を水で数回洗浄し、減圧乾燥することにより、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを11%、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを18%含む混合物{この他に、4-(フェニルチオ)フェニルジフェニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを19%、フェニル-4-(フェニルチオ)フェニルチオキサントニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを52%含んでいた。}を得た。この混合物は、以下のHPLC分取条件により各フラクションを分取し、1H-NMRにより同定した。また、各フラクションの含有量は、以下のHPLC条件にて、検量線を作成し定量した。また、各フラクションについて、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
装 置:Waters 600 controller(日本ウォーターズ株式会社製)
カラム:Shodex K-2001(昭和電工株式会社製)
溶離液:クロロホルム
流 量:3ml/min
カラム温度:40℃
検出器:Waters2414示差屈折計(日本ウォーターズ株式会社製)
分画間隔:30秒
注入量:500μL
[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェート:
d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)
d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、s)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)
d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)
d6-ジメチルスルホキシド、δ(ppm)8.70(1H、s)、8.46(1H、d)、8.26(1H、d)、8.07(1H、d)、7.53~7.98(10H、m)、7.42~7.46(3H、m)
装 置:LaChrom D-7000型(株式会社日立製作所製)
カラム:Inertsil Ph-3(4.6mmi.d. x 250mm、ジーエルサイエンス株式会社製)
溶離液:メタノール/水/過塩素酸ナトリウム=87/10/3(重量比)
流 量:1ml/min
カラム温度:40℃
検出器:L-7455型ダイオードアレイ検出器(株式会社日立製作所製)
ジチオサリチル酸10.0部及び硫酸300部を撹拌しながら、これに4-(フェニルチオ)フェニルジフェニルスルホニウム ペンタフルオロホスフェート16.8部を徐々に加え、室温(約25℃)で1時間反応させた後、反応溶液を蒸留水3000部中に投入し、生成物を析出させた。これをろ過し、残渣を水で濾液のpHが中性になるまで洗浄して、固体を得た。この固体をメタノール390部に溶かし、10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液997部中に投入した後、室温(約25℃)で2時間撹拌し、有機層を水で数回洗浄し、減圧乾燥することにより、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを収率80%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、d)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液65部」を「5%ヘキサフルオロアンチモン酸カリウム73.8部」に変更したこと以外、実施例1と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロアンチモネート(40)を収率95%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)}。また、赤外吸光分光分析(KBr錠剤法)により、650cm-1付近にSb-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液103部」を「5%ヘキサフルオロアンチモン酸カリウム117.0部」に変更したこと以外、実施例2と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロアンチモネートを11%、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム ヘキサフルオロアンチモネートを18%含む混合物{この他に、4-(フェニルチオ)フェニルジフェニルスルホニウム ヘキサフルオロアンチモネートを19%、フェニル-4-(フェニルチオ)フェニルチオキサントニルスルホニウム ヘキサフルオロアンチモネートを52%含んでいた。}を得た。この混合物は、実施例2と同様のHPLC分取条件により各フラクションを分取し、1H-NMRにより同定した。また、各フラクションの含有量は、実施例2と同様のHPLC条件にて、検量線を作成し定量した。また、各フラクションについて、赤外吸光分光分析(KBr錠剤法)により、650cm-1付近にSb-F結合の吸収を確認した。
[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロアンチモネート:
d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)
d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、s)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)
d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)
d6-ジメチルスルホキシド、δ(ppm)8.70(1H、s)、8.46(1H、d)、8.26(1H、d)、8.07(1H、d)、7.53~7.98(10H、m)、7.42~7.46(3H、m)
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液997部」を「5%ヘキサフルオロアンチモン酸カリウム1132部」に変更したこと以外、実施例3と同様にして、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム ヘキサフルオロアンチモネート(60)を収率78%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、d)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、650cm-1付近にSb-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液65部」を「10%テトラキス(ペンタフルオロフェニル)ホウ酸リチウム92.1部」に変更したこと以外、実施例1と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート(70)を収率95%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)}。また、赤外吸光分光分析(KBr錠剤法)により、980cm-1付近にB-C結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液103部」を「10%テトラキス(ペンタフルオロフェニル)ホウ酸リチウム146部」に変更したこと以外、実施例2と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを11%、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを18%含む混合物{この他に、4-(フェニルチオ)フェニルジフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを19%、フェニル-4-(フェニルチオ)フェニルチオキサントニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを52%含んでいた。}を得た。この混合物は、実施例2と同様のHPLC分取条件により各フラクションを分取し、1H-NMRにより同定した。また、各フラクションの含有量は、実施例2と同様のHPLC条件にて、検量線を作成し定量した。また、各フラクションについて、赤外吸光分光分析(KBr錠剤法)により、980cm-1付近にB-C結合の吸収を確認した。
[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート:
d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)
d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、s)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)
d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)
d6-ジメチルスルホキシド、δ(ppm)8.70(1H、s)、8.46(1H、d)、8.26(1H、d)、8.07(1H、d)、7.53~7.98(10H、m)、7.42~7.46(3H、m)
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液997部」を「10%テトラキス(ペンタフルオロフェニル)ホウ酸リチウム1413部」に変更したこと以外、実施例3と同様にして、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレート(90)を収率79%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、d)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、980cm-1付近にB-C結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液65部」を「5%ヘキサフルオロリン酸カリウム49.4部」に変更したこと以外、実施例1と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロホスフェート(110)を収率95%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)}。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液103部」を「5%ヘキサフルオロリン酸カリウム78.3部」に変更したこと以外、実施例2と同様にして、[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロホスフェートを11%、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム ヘキサフルオロホスフェートを18%含む混合物{この他に、4-(フェニルチオ)フェニルジフェニルスルホニウム ヘキサフルオロホスフェートを19%、フェニル-4-(フェニルチオ)フェニルチオキサントニルスルホニウム ヘキサフルオロホスフェートを52%含んでいた。}を得た。この混合物は、実施例2と同様のHPLC分取条件により各フラクションを分取し、1H-NMRにより同定した。また、各フラクションの含有量は、実施例2と同様のHPLC条件にて、検量線を作成し定量した。また、各フラクションについて、赤外吸光分光分析(KBr錠剤法)により、840cm-1にP-F結合の吸収を確認した。
[4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム ヘキサフルオロホスフェート:
d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.54(1H、s)、8.46(2H、d)、8.27(1H、d)、7.76~8.10(14H、m)、7.60~7.69(4H、m)
d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、s)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)
d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)
d6-ジメチルスルホキシド、δ(ppm)8.70(1H、s)、8.46(1H、d)、8.26(1H、d)、8.07(1H、d)、7.53~7.98(10H、m)、7.42~7.46(3H、m)
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液997部」を「5%ヘキサフルオロリン酸カリウム758部」に変更したこと以外、実施例3と同様にして、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム ヘキサフルオロホスフェート(130)を収率79%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.53(1H、s)、8.47(1H、d)、8.00(1H、d)、7.69~7.92(15H、m)、7.65(1H、t)、7.54(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
製造例1で合成した2-(フェニルチオ)チオキサントン15.0部、ジフェニルヨードニウムヘキサフルオロホスフェート41.9部、安息香酸銅(II)0.4部及びクロロベンゼン300部を均一混合し、120~125℃で3時間反応させた後、反応溶液を室温(約25℃)まで冷却し、蒸留水300部中に投入し、生成物を析出させた。これをろ過し、残渣を水で濾液のpHが中性になるまで洗浄し、残渣を減圧乾燥した後、トジエチルエーテル100部を加えて超音波洗浄器でジエチルエーテル中に分散し約15分間静置してから上澄みを除く操作を3回繰り返して、生成した固体を洗浄した。ついで、固体をロータリーエバポレーターに移して、溶媒を留去することにより、黄色固体を得た。この黄色固体をジクロロメタン770部に溶かし、10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液342部中に投入した後、室温(約25℃)で2時間撹拌し、有機層を水で数回洗浄し、減圧乾燥することにより、ジフェニル-2-チオキサントニルスルホニウム トリス(ペンタフルオロエチル)トリフルオロホスフェートを収率98%、純度85%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.47(1H、d)、8.30(1H、d)、8.13(2H、d)、7.78~7.98(11H、m)、7.70(1H、t)}。純度はHPLCにより(HPLC条件は上記と同様である。)により定量した。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
ジフェニルスルホキシド12.1部、ジフェニルスルフィド9.3部及びメタンスルホン酸43.0部を撹拌しながら、これに無水酢酸7.9部を滴下し、40~50℃で5時間反応させた後、室温(約25℃)まで冷却し、この反応溶液を20%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液121部中に投入し、室温(約25℃)で1時間撹拌して、黄色のやや粘調な油状物が析出した。この油状物を酢酸エチルにて抽出し、有機層を水で数回洗浄した後、有機層から溶剤を留去し、得られた残渣にトルエンを加えて溶解した後、ヘキサンを加え、10℃で1時間よく撹拌した後静置した。1時間後、溶液は2層に分離したため、上層を分液によって除いた。残った下層にヘキサンを加え、室温(約25℃)でよく混合すると淡黄色の結晶が析出した。これをろ別し、減圧乾燥して、4-(フェニルチオ)フェニルジフェニルスルホニウムトリス(ペンタフルオロエチル)トリフルオロホスフェートを収率60%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、840cm-1付近にP-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液342部」を「5%ヘキサフルオロアンチモン酸カリウム388.4部」に変更したこと以外、比較例1と同様にして、ジフェニル-2-チオキサントニルスルホニウム ヘキサフルオロアンチモネートを収率97%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.47(1H、d)、8.30(1H、d)、8.13(2H、d)、7.78~7.98(11H、m)、7.70(1H、t)}。また、赤外吸光分光分析(KBr錠剤法)により、650cm-1付近にSb-F結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液342部」を「10%テトラキス(ペンタフルオロフェニル)ホウ酸リチウム484.6部」に変更したこと以外、比較例1と同様にして、ジフェニル-2-チオキサントニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを収率97%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.47(1H、d)、8.30(1H、d)、8.13(2H、d)、7.78~7.98(11H、m)、7.70(1H、t)}。また、赤外吸光分光分析(KBr錠剤法)により、980cm-1付近にB-C結合の吸収を確認した。
「20%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液121部」を「10%テトラキス(ペンタフルオロフェニル)ホウ酸リチウム342.9部」に変更したこと以外、比較例2と同様にして、4-(フェニルチオ)フェニルジフェニルスルホニウム テトラキス(ペンタフルオロフェニル)ボレートを収率60%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)7.72~7.87(12H、m)、7.54~7.63(5H、m)、7.42(2H、d)}。また、赤外吸光分光分析(KBr錠剤法)により、980cm-1付近にB-C結合の吸収を確認した。
「10%トリス(ペンタフルオロエチル)トリフルオロリン酸カリウム水溶液342部」を「5%ヘキサフルオロリン酸カリウム260.1部」に変更したこと以外、比較例1と同様にして、ジフェニル-2-チオキサントニルスルホニウム ヘキサフルオロホスホスフェートを収率97%で得た。生成物は1H-NMRにて同定した{d6-ジメチルスルホキシド、δ(ppm)8.72(1H、s)、8.47(1H、d)、8.30(1H、d)、8.13(2H、d)、7.78~7.98(11H、m)、7.70(1H、t)}。また、赤外吸光分光分析(KBr錠剤法)により、540cm-1付近にP-F結合の吸収を確認した。
CPI-101A{4-(フェニルチオ)フェニルジフェニルスルホニウム ヘキサフルオロアンチモネートの50%プロピレンカーボネート溶液、サンアプロ株式会社製}を比較用のスルホニウム塩(H70)とした。
CPI-100PA{4-(フェニルチオ)フェニルジフェニルスルホニウム ヘキサフルオロホスフェートの50%プロピレンカーボネート溶液、サンアプロ株式会社製}を比較用のスルホニウム塩(H80)とした。
評価試料{実施例1~12及び比較例1~8で得たスルホニウム塩}と、溶媒(プロピレンカーボネート)とを表1に示した配合量(重量部)で均一混合してスルホニウム塩溶液を調製し、この溶液と、エポキシド(3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、ダウケミカル株式会社製、UVR-6110)とを表1に示した配合量(重量部)で均一混合して、エネルギー線硬化性組成物を調製した。
◎:鉛筆硬度が2H以上
○:鉛筆硬度がH~B
△:鉛筆硬度が2B~4B
×:液状~タックがあり、鉛筆硬度を測定できない
・紫外線照射装置:ベルトコンベア式UV照射装置(アイグラフィックス株式会社製)
・ランプ:1.5kW高圧水銀灯
・照度:条件-1a;260mW/cm2(365nmヘッド照度計で測定)
条件-2a;182mW/cm2(405nmヘッド照度計で測定)
条件-3a;64mW/cm2(405nmヘッド照度計で測定)
条件-2a;2300mJ/cm2(405nmヘッド照度計で測定)
条件-3a;1940mJ/cm2(405nmヘッド照度計で測定)
条件-1b;960mJ/cm2(365nmヘッド照度計で測定)
条件-2b;12430mJ/cm2(405nmヘッド照度計で測定)
条件-3b;6470mJ/cm2(405nmヘッド照度計で測定)
条件-1b~3bは、条件-1a~3aよりも照射時間を長くしたこと以外、条件-1a~3aと同じである。
条件-2a、b;L-39(株式会社ケンコー光学製、390nm以下の光をカットするフィルター)
条件-3a、b;L-42(ケンコー光学社製、420nm以下の光をカットするフィルター)
c1 [4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウム
c2 [4-(2-チオキサントニルチオ)フェニル]フェニル-2-チオキサントニルスルホニウムと、[4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウムとの混合物
c3 [4-(2-チオキサントニルチオ)フェニル]ジフェニルスルホニウム
c4 ジフェニル-2-チオキサントニルスルホニウム
c5 4-(フェニルチオ)フェニルジフェニルスルホニウム
a2 ヘキサフルオロアンチモネート
a3 テトラキス(ペンタフルオロフェニル)ボレート
a4 ヘキサフルオロホスフェート
Claims (9)
- 式(1)で表されることを特徴とするスルホニウム塩。
(式(1)中、R1は式(2)で表される基、R2及びR3はそれぞれ炭素数6~30のアリール基、炭素数4~30の複素環式炭化水素基、炭素数1~30のアルキル基、炭素数2~30のアルケニル基又は炭素数2~30のアルキニル基を表し、これらのアリール基、複素環式炭化水素基、アルキル基、アルケニル基又はアルキニル基の水素原子の一部が置換基(t)で置換されていてもよい。Sは硫黄原子、X-は一価の多原子アニオンを表す。)
(式(2)中、R4~R6はそれぞれアルキル基、ヒドロキシ基、アルコキシ基、アルキルカルボニル基、アリールカルボニル基、アルコキシカルボニル基、アリールオキシカルボニル基、アリールチオカルボニル基、アシロキシ基、アリールチオ基、アルキルチオ基、アリール基、複素環式炭化水素基、アリールオキシ基、アルキルスルフィニル基、アリールスルフィニル基、アルキルスルホニル基、アリールスルホニル基、ヒドロキシ(ポリ)アルキレンオキシ基、アミノ基、シアノ基、ニトロ基又はハロゲン原子、k、m及びnはそれぞれR4、R5、R6の数を表し、kは0~4の整数、mは0~3の整数、nは0~4の整数であり、Aは-S-、-O-、-SO-、-SO2-又は-CO-で表される基、Oは酸素原子、Sは硫黄原子を表す。) - R2又はR3がそれぞれ炭素数6~30のアリール基又は炭素数4~30の複素環式炭化水素基である請求項1に記載のスルホニウム塩。
- R2又はR3がフェニル基であり、Aが-S-で表される基であり、k、m及びnが0である請求項1に記載のスルホニウム塩。
- R2又はR3がチオキサントニル基であり、Aが-S-で表される基であり、k、m及びnが0である請求項1に記載のスルホニウム塩。
- X-がMYa -、(Rf)bPF6-b -、R7 cBY4-c -、R7 cGaY4-c -、R8SO3 -、(R8SO2)3C-又は(R8SO2)2N-で表されるアニオン(Mはリン原子、ホウ素原子、ヒ素原子又はアンチモン原子、Yはハロゲン原子、Rfは水素原子の80モル%以上がフッ素原子で置換されたアルキル基、Pはリン原子、Fはフッ素原子、R7は少なくとも1個の水素原子がハロゲン原子、トリフルオロメチル基、ニトロ基又はシアノ基で置換されたフェニル基、Bはホウ素原子、Gaはガリウム原子、R8は炭素数1~20のアルキル基、炭素数1~20のパーフルオロアルキル基又は炭素数6~20のアリール基、Sはイオウ原子、Oは酸素原子、Cは炭素原子、Nは窒素原子を表し、aは4~6の整数、bは1~5の整数、cは1~4の整数を表す。)である請求項1~4のいずれかに記載のスルホニウム塩。
- X-が、SbF6 -、AsF6 -、PF6 -、BF4 -、(CF3CF2)3PF3 -、(C6F5)4B-、((CF3)2C6H3)4B-、(C6F5)4Ga-又は((CF3)2C6H3)4Ga-で表されるアニオンである請求項1~4のいずれかに記載のスルホニウム塩。
- 請求項1~6のいずれかに記載のスルホニウム塩を含有することを特徴とする光酸発生剤。
- 請求項7に記載の光酸発生剤とカチオン重合性化合物とを含有することを特徴とするエネルギー線硬化性組成物。
- 請求項8に記載のエネルギー線硬化性組成物を硬化して得られることを特徴とする硬化体。
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EP09742607A EP2284165B1 (en) | 2008-05-06 | 2009-04-27 | Sulfonium salt, photoacid generator, photo-curable composition, and cured product of the photo-curable composition |
US12/989,549 US8278030B2 (en) | 2008-05-06 | 2009-04-27 | Sulfonium salt, photoacid generator, and photocurable composition and cured body thereof |
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EP (1) | EP2284165B1 (ja) |
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KR (1) | KR101567115B1 (ja) |
WO (1) | WO2009136482A1 (ja) |
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JP2009269849A (ja) | 2009-11-19 |
KR20110020767A (ko) | 2011-03-03 |
EP2284165A4 (en) | 2011-04-27 |
EP2284165B1 (en) | 2013-02-20 |
JP5208573B2 (ja) | 2013-06-12 |
EP2284165A1 (en) | 2011-02-16 |
KR101567115B1 (ko) | 2015-11-06 |
US20110039205A1 (en) | 2011-02-17 |
US8278030B2 (en) | 2012-10-02 |
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