TW205055B - - Google Patents
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- Publication number
- TW205055B TW205055B TW081102635A TW81102635A TW205055B TW 205055 B TW205055 B TW 205055B TW 081102635 A TW081102635 A TW 081102635A TW 81102635 A TW81102635 A TW 81102635A TW 205055 B TW205055 B TW 205055B
- Authority
- TW
- Taiwan
- Prior art keywords
- salt
- sulfur
- iridium
- base
- group
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 49
- 239000007789 gas Substances 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- -1 Sulfur Iridium Salts Chemical class 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 239000011593 sulfur Substances 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000009434 installation Methods 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims 4
- 239000005864 Sulphur Substances 0.000 claims 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 2
- OIENHJCGDAGWEG-UHFFFAOYSA-N [Ir]=S Chemical compound [Ir]=S OIENHJCGDAGWEG-UHFFFAOYSA-N 0.000 claims 2
- 229910052804 chromium Inorganic materials 0.000 claims 2
- 239000011651 chromium Substances 0.000 claims 2
- 150000003463 sulfur Chemical class 0.000 claims 2
- 239000004135 Bone phosphate Substances 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- XAQHXGSHRMHVMU-UHFFFAOYSA-N [S].[S] Chemical compound [S].[S] XAQHXGSHRMHVMU-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- 150000002503 iridium Chemical class 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 5
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 4
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 241000723353 Chrysanthemum Species 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 150000000918 Europium Chemical class 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920001633 poly(α-methyl styrene) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000069 polyphenylene sulfide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- CPGPAVAKSZHMBP-UHFFFAOYSA-N 9-methylanthracene Chemical compound C1=CC=C2C(C)=C(C=CC=C3)C3=CC2=C1 CPGPAVAKSZHMBP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229910052695 Americium Inorganic materials 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AAKIJEFDKZTZIK-UHFFFAOYSA-N CC(C=C1)=CC=C1S(=O)=O.Cl Chemical compound CC(C=C1)=CC=C1S(=O)=O.Cl AAKIJEFDKZTZIK-UHFFFAOYSA-N 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- ODEGFPCTGGIJCF-UHFFFAOYSA-A P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+] Chemical compound P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].P(=O)([O-])([O-])[O-].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+].[K+] ODEGFPCTGGIJCF-UHFFFAOYSA-A 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 102100034757 Thiol S-methyltransferase METTL7B Human genes 0.000 description 1
- 101710082490 Thiol S-methyltransferase METTL7B Proteins 0.000 description 1
- DPSZMPUXFZOWAC-UHFFFAOYSA-N [S].S=O Chemical compound [S].S=O DPSZMPUXFZOWAC-UHFFFAOYSA-N 0.000 description 1
- HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical class [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 description 1
- JWUIMIOWSYWXBQ-UHFFFAOYSA-N [Sn].O=S Chemical compound [Sn].O=S JWUIMIOWSYWXBQ-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- LXQXZNRPTYVCNG-UHFFFAOYSA-N americium atom Chemical compound [Am] LXQXZNRPTYVCNG-UHFFFAOYSA-N 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- MKJZCTBDSBFQFT-UHFFFAOYSA-K bis-(4-methylphenyl)sulfonyloxybismuthanyl 4-methylbenzenesulfonate Chemical compound [Bi+3].Cc1ccc(cc1)S([O-])(=O)=O.Cc1ccc(cc1)S([O-])(=O)=O.Cc1ccc(cc1)S([O-])(=O)=O MKJZCTBDSBFQFT-UHFFFAOYSA-K 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical group [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- JTPACTAWYIXPSB-UHFFFAOYSA-N chloro(triphenyl)-$l^{4}-sulfane Chemical compound C=1C=CC=CC=1S(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JTPACTAWYIXPSB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 150000002178 europium compounds Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical group 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NMHTWXYFOWTMJH-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(=O)OCC1CO1 NMHTWXYFOWTMJH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- JVUYWILPYBCNNG-UHFFFAOYSA-N potassium;oxido(oxo)borane Chemical compound [K+].[O-]B=O JVUYWILPYBCNNG-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 229960004134 propofol Drugs 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- RVKZDIDATLDTNR-UHFFFAOYSA-N sulfanylideneeuropium Chemical compound [Eu]=S RVKZDIDATLDTNR-UHFFFAOYSA-N 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
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Description
205053 . λ, 五、發明.説明(,) 本發明偽闊於一種新穎的硫氣銪鹽類。 ' 已知有許多種硫氧鎬穿類被用來做為陽離子性可聚合 材料之光聚合的引發劑,如環氣樹脂。我們現在發展出 一種新的硫氣錨鹽類,其與環氣樹脂具有更高的相容性 ,並且釋放出較少的揮發性物質或可瀝濾物質於熟化的 薄膜中,而在許多的倩形下這也意味者其會産生較少的 氣味。 因此,本發明可提供一種芳基硫.氣錨鹽,其可為在分 子中包含一種可聚合之基團,或者是為聚合化合物中的 —部分。 _ ί 本發明之硫氣銷鹽可以是一種三芳基硫氣_鹽,其中 有一値芳基是側接於聚合鐽上,或是被一値可聚合之基 \ 圍所取代;或者是此硫氯錨鹽基国傜位於聚合物的主鐽 中。 (請先閲讀背而之注意事項再埸寫本頁) 裝· 經濟部屮央標準而貝工消作合作社印^ 如 1 子於 ,酌 式 , 是原接 上或 通 圍者碩聯 鏈基 學 基或個鐽 於苯 化 的 ,4 學 接由 的 鏈基至化 連绖 面 稀酸 1 的 接如。下 和烯含?)直例接如 飽丁由 U 可,連, 未異fis/f它±鍵例 氧 有是可 ί ,團主實 含或圃 時基與的 些基基 π 上的而物 那酸合¾趙接子合 為烯聚λι合侧原化 固丙可6Λ聚所氣之 基、。Μ 於上個画 合基圍tie·接sil 基 聚丙基Μ 迪於由合 可烯物g-Γ偽接經聚 的、化7S。基連是可 適基氣1Π上芳是者有 合烯琛 Μ 基當者或含 乙2-< :方 或基 81. 4.】0,00〇張(H) 本紙张尺度边用中Η國家楳準(CNS)Τ4規格(210X297公龙) ^0505d
Λ 6 15 G 五、發明説明()) (I )所示:
經濟部屮央標準而A工消作合作社印3i (I) 其中R包括一個丙烯酸酯(異丁烯酸酯)、乙烯醚、烯 丙醚或者是環氣基團;X和Z可相同或相異,其傜代表 單價的取代基,如鹵素或烷基;而P和q可相同或相異 ,為零或者是小於六的整數。例如R可為(]{{2=(^(:00- CH„ = C (CH3) COO- 、 CHa = CHC00CHaCH(0H)CH,0-、 CHB=C(CH)3C00CH,CH(0H)CHa0-、 CHa=CH-CHs0-,或者是 CH<-尸-CH. 0 - 0 0 芳基連接於聚合鏈之化合物的實例包括聚合物為含有 苯基之聚合物,或者是為琛氣樹脂之聚合物。適合的含 苯基之聚合物包括聚U -甲苯乙烯)、聚(4 -乙烯基苯酚 )、和苯酚酚醛淸漆。 當此硫氣錨鹽為聚合物中的一部分時,它可出現在主 鏈上2 5到7 5 %的可能位笪上,或者硫氣錨鹽可為苏聚物 的端基。 硫氣錨鹽的陰離子可以為一迪種簡單的陰離子,如鹵 (請先閲讀背而之注意事項#填寫和負) 裝· 訂_ 線- 本紙張尺度边用中國困家«毕(CNS) 規格(210x297公;«:) 81. 10,000張(H) 經濟部屮央標準β工消你合作社印製 Λ〇 _______Η_6 五、發明説明(4 ) 化物(例如氯化物或溴化物)、三氟甲烷磺酸鹽,或者較 好是如下列化學式(II)之離子: MYm - (II) 其中Μ為一種金屬原子或是準金屬原子:Y為一種鹵 素原子,如氟或氯;而m為4, 5或6,並且其數值需大於 Μ的原子價數。Μ可為硼、鉍、銻、砷或是磷。因此這 種離子可為 BiCle- 、BF4- 、PFS_ 、SbFs-或 A s F 6 — 〇 本發明中含有可聚合基園之化合物可以用下列的任一 種方式來製造:將含反應性基團的芳基硫氧錨鹽,與可 .將所需可聚合基團引入之化合物反應;或者是將含反應 性基團的芳基硫銷鹽,與可將所需可聚合基團引入之化 合物反應,然後再將硫銪鹽的部分氧化成硫氣_鹽。 適合的硫氧錨鹽化合物包括那些具有酚式氫基或是鹵 素原子的基團。而可將可聚合基圃引入的化合物則己括 丙烯醯(異丁烯醯)_、丙烯酸(異丁烯酸)縮水甘油酯、 烯丙醇、乙烯醇、縮水甘油、烯丙基鹵和環氣樹脂,而 這些化合物可能是己被升级過的。 本發明的化合物中,若靥於硫氣銳基團為聚合物的一 部分者,可以Μ著含反應性基圃(如羥基或齒素)之识合 物與含有可與聚合物上的反應:性毡圍反應之越_的硫銳 鹽類或者是硫氣錨鹽類反憋(如有豁要亦可以已知的方 法,將硫錨鹽轉換成其相對應的硫氣錨鹽)而製得;或 本紙張尺度边用中a®家«毕(CNS)T4規格(210x297公:《:) 81. 4.】0,000張(H) (請先閲讀背而之注意事項#塡寫奢备) 裝· 線· 經濟部中央標準局A工消#合作社印¾ —----- -l^c__ 五、發明説明(今) 者是將芳香族聚合物與一種二芳基的硫氧化合物反應, 而産生一種含硫錨發單元的聚合物,然後再將硫錯基的 部分加以氣化而形成硫氣錨基。 本發明的化合物中',若屬於硫氣錨基團傜在聚合物的 主鐽中者,則可《由將已知的相對應硫鍩化合物氧化來 製備。硫錨化合物可依過去已知的方式由聚(苯撐硫化 物)來製備,例如與二苯碘鹽反應。鹽類基團可出現在 2 5到1 0 0 %的可用位置上(硫化物基圍傜在起始聚合物中 )較好是能100%出現在可用的位置上β 本發明之化合物可做為陽離子可聚合材料的光抑制劑 。其使用量可為可聚合材料之重量的0 . 1 %到3 0 . 0 % , 以0 · 5 %到1 0 %為佳。 ' 它們比其它相對應的硫_鹽類的陽離子光引發劑效果 佳。 有許多種陽離子可聚合材料可使用本發明之化合物來 進行光聚合反應,例如在美國專利第4 3 3 9 5 6 7 5¾中所述 之物質,包括環氣化合物、乙烯化合物、氨基塑料和酚 菸塑料。較佳的化合物為芳香族的缔水甘油酤,特別是 芳香族的缩水二甘油醅。 硫氣銪化合物可單獨使用,或是與敏化劑一起使用, 以增加熱化的速度。適合的敏化劑包括染料或芳番族的 多琛化合物,如恝、9 -甲甚恝,红螢烯、ft;、危、菲、 氣恝烯和芘。其它種適合的敏化劑在美國羿利第4 fl 6 9 0 5 4 (請先閲:f?背而之注意事項再填寫本頁) 裝- 線. 本紙尺度边用中Η困家標準(CNS) 1M規彷(210x297公龙) 81. 4.】0,000張(II) -.ϊ-ί 經濟部屮央伐準:?β工消费合作社印製 Λ Π6 五、發明説明(r ) 號中之有敍述。 本發明之化合物將釋放出較少的揮發性物質或是可歷 滹的物質於熟化的薄膜中,與環氣樹脂有較高的相容性 ,較少發生鹽集的現象,並且具有較低的毒害性。 下面以一些例子來説明本發明。 例1 關於聚(α-甲基-苯乙烯)之聚合物:
Ph2S=0 pf6- 將苯基硫氧化物(7.26克,0.036莫耳)和聚(α -甲基-苯乙烯)(7.1 4克,0.Q72莫耳,分子量為81000)溶解於二 氯甲烷(S 0毫升)中,並且以在冰水浴中攪拌的方式來 冷卻。接著先將三氟醋酸酐(5 . 1 6克,0 . 0 7 2莫耳)滴入, 再將三頟甲烷磺酸(3.24克,0.036契耳)分別滴入。在 抿拌30分鐘之後,將此混合物加熱至室溫,並維持18値 小時以上。之後將反應混合物慢慢加入醚中。將艇予以 倾析,並且將殘留物S入甲醉中。將此甲醇i容液滴入六 氣磷酸鉀的水ί容液中。在低壓下將甲醉除去。將所将之 固體予以收渠並用水加以沖诜,然後再以_沖洗,以産生 本紙尺度边用中Η Η家榀毕(CNS) Τ4規格(210X297公龙) 81. 4. 10,000¾ (11) (請先閱詒背而之注意事項再填寫本頁) 裝- 訂· 線-
Λ 6 Η G 20505ο 五、發明説明(b ) 一種固體(12.4克)。 將這種鹽類(1.0克)和對甲苯磺醛氯(2.38克,0.0125 莫耳)溶於二氯甲烷(4 0毫升)中所形成之溶液予以攪伴, 並在冰水浴中冷卻。在2 5分鐘内,將過氧化納(2 · 4 2克, 0.031莫耳)之水溶液(水佔30毫升)慢慢滴入。再攪痒1.5 個小時之後,停止攪拌,並且使溶液分離成二層,收集 下層(亦即有機層),使其在低壓下乾燥及濃縮。以醚來 沖洗所得之棕色殘留物,而産生漿狀的聚合硫氧銷鹽( 〇 · 8 1克)。依下列方式將小量的鹽類加以純化:將鹽類 溶於丙酮/水中,並且加入六氟磷酸,使pH值調整為4-5 之間。將水加入其中,並以真空除去丙酮。收集所得的 物質後,以水和ffi加以沖洗而産生棕色固體狀的聚合硫 氧銪鹽,熔點為7 9 - 8 4 °C之間。 核磁共振光譜(ds-丙酮):δ 2.1(s),7.g-8.05(m),8.2(n〇 紅外線光譜(溴化鉀片):1570,1450,1080,845,750,730, 7 0 0 , 6 8 0 公分-1 例 2 (a )被鎘取代之硫親鹽中間體: (請先閲讀背而之注意事項冉填寫本頁) 裝. 線· 經濟部屮央榀準而β工消1V-合作社印¾
F
pf6· 本紙度逍用中a Η家榣準(CNS) TM規格(210X297公龙) 81. 4. ]0,000張(||)
Λ 6 Π G 2050bo 五、發明説明(7) 将苯基硫氣化物(1 0克,4 9 . 5毫莫耳)溶解於氟苯(5 0 毫升)中,並且在攪拌的情況下冷卻至0 °C。接著先將三 氟醋酸酐(2Q.8克,14毫升,99毫莫耳)滴入,再將三氟 甲烷磺酸(4.4毫升,49. 5毫莫耳)分別滴入。將此混合 物再攪拌1 8痼小時,並加熱至室溫。之後將剩餘的氟苯 在低壓下除去,並且將殘留物置入甲醇水溶液中。將此 溶液滴入過量的六氟磷酸鉀水溶液中。將此産物在二氯 甲烷中萃取三次,並將所得之有機相予以乾燥。在低壓 下除去溶劑,以産生油狀的被氟取代之硫銪鹽(1 Q . 9 5克 ,5 2%)。 紅外線光譜(溴化鉀片):1590,1500, 1480, 1450, 1250, 1 1 6 5 , 8 4 0 , 7 5 0 , 6 8 5 公分-1 核磁共振光譜((15-丙_): δ 7.65(m,2H),7.9(m,10H), 8 . 0 5 (πι , 2 Η ) (b )氟鹽和聚(4 -乙烯基苯酚)的反婼可捋, (請先閲讀背而之注意事項#填寫t為) 裝. 線- 經濟部十央榀準而KX工消"合作社印製
-9 81. 4. 10,000¾ (!1) 1紙5 艮尺度逍用中 2〇5〇υα Λ 6 Π 6 經濟部屮央梂準/(0A工消合作社印3i 五、發明説明(8) 將二苯基(氟苯基)硫_化六氟磷酸(3.0克,0.007莫 耳)聚(4 -乙烯基苯酚)(1.68克,0·014莫耳的ΟΗ基)置入 二甲基硫氧化物(90毫升)中,並在80-100 Ό的溫度下攪 拌1 8値小時。之後將此反應混合物加以冷卻,並且滴入 水中。收集所得之固體,以醚加以沖洗並使之乾燥。 將産物的一部分(1克)與對甲苯磺醯氣(1.75克, 0.009莫耳)一起溶解於二氛甲烷(40毫升)中。將此混合 物加以攪拌,並在冰水浴中冷卻。在2 0分鐘的時間内, 將過氧化納(1 . 8克,0 . 0 2 3莫耳)之水溶液(水佔3 0毫升) 慢慢滴入。接著再攪拌30分鐘之後,停止攪拌,並且使 溶液分離成二層。以水和二氣甲烷來烯釋溶液層,並且 以嬝度為2Μ的鹽酸使混合物酸化。收集下面的有機層, 使其在低壓下乾燥及濃縮。收集所得之固體,並以_來 沖洗,而産生橘色固S狀的聚合硫氧錯鹽(Q.47克),其 與例3中之産物的光譜分析結果相同。 例 3 由被氯取代之硫氣_鹽所得之聚合硫氣錡鹽。與例2 中的産物相同。 將聚(4 -乙烯基苯酚)(0.28克,0.0023契耳)、二苯基 氯苯基硫氣錨化六氟磔酸,與在二甲基硫氣化物(90亳 升)中之磺酸狎(〇 · 9 6克,0 . Q 0 7契耳)所形成之混合物予 以攪拌並在1 ϋ ϋ °C的溫度下加Μ 1 8値小時。之後將此反 應混合物加以冷卻,並且倒入六氟磷酸鉀的水溶液中。 -1 0 - (請先閲讀背而之注意事項#塡t¾) 裝· 訂 線_ 本紙5fc尺度边用中國困家楳準(CNS) 規格(210x29·/公;¢) 81. 4. 10,000¾ (H)
2050〇S
Λ 6 H C 五、發明説明(彳) 收集所得之沈澱物,以醚加以沖洗《藉著將此産物溶解 於丙酮/水中而使之纯化,加入六氟磷酸水溶液(使p Η 值調至4-5)並且加入大量的水。收集所得之灰白色固體 ,加以沖洗並在真空下乾燥而産生聚合硫氧錫鹽(1 . 1 1 克)。熔點為1 8 5 - 2 Q 1 °C。 红外線光譜(溴化鉀片):1590,1510,1490,1085,850,760, 7 3 0公分-, 核磁共振光譜((U -丙酮):δ 2.4(寬),6.8-7.6(寬),7.9-8.1(¾) 例4
(請先閲請背而之注意事項再塡寫β
S 裝· 經濟部屮央標準局β工消"合作社印製 將二苯基(羥苯基)硫氣銪化六氟磷酸(1 . 〇克,〇 . 〇 〇 2 3 Μ耳)、烯丙溴(3 . 0毫升)和碳酸鉀(1 . 5克)溶解於5 0毫 升的丙飼中,並予以搜拌。加熱至6 5 °C ,持續1 8個小時 -1 1 - 本紙張尺度边用中Β國家標準(CNS) Τ4規格(210X297公;Ϊ) 81. 4. 10,000¾ (II) A 6 Π 6 五、發明説明(π) 。之後將此反腠混合物予以過濾,並且在低壓下濃縮。 加入91,並且使此混合物在真空中蒸發,而産生黃色油 狀的産物(0.21克,19%)。 核磁共振光 _(de-丙酮):δ 4.85(b,2H), 5.4(ddm,2H), 6.1(n,lH),7.5(d,2H),8.05(m,6H) 紅外線光譜(液膜):1600, 1450 ,1280, 1090 ,850,760, 740, 6 9 0公分… 例5 先 閲 背 而 之 注 意 事 項 再 m % 本一 t 裝 由
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Ph2S=0 PF, 將二苯基(氟苯基)硫銪化合物六氟磷酸(6. q克,〇.〇14 莫耳)、烯丙醇(1.8毫升,0.〇3契耳)'和碩酸鉀(5.76克 ,〇·(Η莫耳)置入二甲基硫氣化物(180窀升)中,並加熱 至8 0 - 1 0 Q°C,持壤1 8小時。之後將此反應混合物予以冷 卻並倒入水中。將此産物以二氮甲烷來萃取,並在低壓 下予以乾燥和濃縮。所得之産物以醚來冲洗,而産生一 12 本紙張尺度边用中β B家撑毕(CNS) T4規格(210x297公;«:) 81. 4. ]0,000張(Η) ιΟ Λ 6 η g 五、發明説明(<') 〆 種含有二甲基硫氣化物之棕色油(9.9克)。 將這種油的一部分(1克)以例1所述的方式來氧化, 而産生被烯丙基取代之硫氣_鹽(ϋ · 2 4克,3 7 % ),其為 黃色的蠟,其光譜分析结果與例4相同。 例 6 由 ΟΗ
Ph2S=〇 來合成 0
Ph2S=0 閲 in 背 而 之 注 意 事 項 寫 才 1 將耳 莫 基 苯 甲 二 和 嘧 基基 F6-苯氨 P羥基 硫 啶 毫氣 91二 ο 於 ,置 克?) 4 耳 F6-0 莫 ^ 2 氟 , 六克 匕 5 /1 2 0 ο 氣t 克將卻 -1* •,冷 (0後以 氯之予 醒時質 烯小物 丁値的 異18色 將拌紅 。攪粉 拌绩之 It繼得 下再所 溫。將 室入 〇 在加中 ,慢¾ )ψι^1人 丨丨倒 物 合 混 烷1.應 甲 ,反 升耳 毫莫 2 毫 鹽 烯 丁 異 生 .¾ 而 洗 中 *./1 以 JD0 以 再 洗 冲)o 水% 以51 先 , -克 經濟部屮央標準局EX工消贽合作社印製 0 光 振 共 磁 核 膜 薄 /IX 譜 光 線 外 紅 酮 丙 分 公 本紙尺度逍用中《困家標準(CNS) T4規格(210X297公;¢) 81. 4. 10,000張(H) Λ 6 Η 6 五、發明説明(θ) 例 Ί 酚醛清漆與硫氧_鹽之加合物
PF, R = 25% But 75% Η 重覆例3之步驟,但以A 1 η o v a 1 Ρ Ν 4 3 G聚合物來取代 聚(4 -乙烯基苯酚)。所得之産物的熔點為169-176。0。 核磁共振光譜(ds -丙酮):5 7.9-8. 2(n), 3. 8(n)寬峰 紅外線光譜(溴化鉀 Η ) : 1585,1490,1250,1085,850,755 7 1 〇 , 6 85 公分· 1 例 8 ΟΗ 過 级 升 先. A 0 ) «0.又 K 以汕 ( f— 0 y 15水 6縮 TEn 1 A LD酚 RAS又 A之 和 ?· 先 閲讀. 背 而 之 注 意 事 項 再 填 寫〜 4 % 裝 訂 線 經濟部中央榀準局貝工消#合作杜印製
P + IPF; 磷 氟 六 化 0 氧 硫 \)/ 基 苯 羥 /f\ 基 〇 苯 物二 成將 加 克 毫 本紙張尺度逍用中8囤家標毕(CNS)T4規格(210X297公¢) 81. 4.丨0,000張(H) Λ 6 ___HC_ 五、發明説明(θ) 莫耳)和A R .A L D I Τ Ε 6 1 5 Ο ( 1 . Ο 5克,1 · 7毫莫耳的環氧化物 基圍)一起研磨,並且在1 5 Q °C的溫度下加熱二小時。將 此混合物加以冷卻,並且溶解於丙銅和水中。加入六氟 磷酸(濃度為6 0 % )直到p Η值约為4為止,並將此溶液加 至水中。在低壓下將丙酮除去,並且將此懸浮液加以過 濾。以水來沖洗此固體産物,並在真空中乾燥》産量為 〇 . 6 1 克,熔點為 1 0 2 - 1 0 8 °C。 核磁共振光譜(ds-丙酮):5 1.60(5),3.00(111),3.90- 4.20(b),6.85(d), 7. 16(d), 7.52(d), 7.99(b) ,8 · 1 6 ( m ) 寛峰 紅外線光遒(溴化鉀片):3500(br), 1610, 1590,1510, 1250 ,1180,1085,1040,830,760,730, 6 8 0公分· 1 例 9 (請先間請背而之注意事項#堝寫^¾) 裝· 訂 線·
OH
經濟部屮央榀準而A工消讣合作社印3i 和異丁烯酸縮水付油酯之.加成物 4*
Ph2S=0 pf6' 將二苯基(羥苯基)硫铽微化六碱磷酸(1 · Q克,2 · 3毫 '莫耳)和異丁烯酸酯水甘油酯(1 . G克,7 . Q毫莫耳)在2 . 6 -15- 本紙張尺度逍用中國B3家標準(CNS)T4規格(210X297公龙) 81. 4· 10,000張(Ιί) Λ 6 Π 6 五、發明説明(ι4〇 -二-特丁基-對甲酚(Ο . 〇 5克)中在1 5 0°c的溫度下加熱2 . 5 小時;而産生加成物和聚合物之混合物。 核磁共振光譜(ds -丙酮):δ 1.05(m), 1.9(id), 3.4-4.6 (π),5.6(π),6.05(πι)17.5(ηι),8.0(ιη),8.1(πι) 紅外線光譜(薄膜):3300, 1720,1590,1450,1180,1075, 8 4 5 , 7 6 0 , 7 3 5 , 7 2 0 公分-* 例 10
(請先閲誚背而之注意事項孙填窵木為) 裝. 經浒部屮央標準杓β工消作合作社印奴 + Ph2S=0 pf6- 將二苯基(氟苯基)硫銳化六氟磷酸(3.0克,7毫莫耳) 、縮水甘油(1 · 2毫升,1 4毫莫耳)和碩酸鉀(2 . 8 8克,2 1 毫莫耳)置入二甲基硫氣化物(1 0 0毫升)中,並加熱至 1 〇 〇 °C ,持_ 1 8個小時。之後將此反憋混合物予以冷卻 並倒入水中。將此迮物以二氮甲烷來萃取,並在低壓下 予以乾燥和溫縮。所得之産·物以二乙®來冲洗,而症生 一種棕色的油(3 · 1克)。將迠極油的一部分(1克)與對 甲苯磺鏜鉍(2 · 3 8克,1 2 . 2窀Μ耳)溶解於甲酵(4 ϋ奄升) -1 6 - 線· 本紙張尺度边用中ffl國家標毕(CNS) 規格(210x297公:《:) 81. 4. 10,000¾ (II)
Λ 6 Π G 五、發明説明(β) 中。將此混合物加以搜伴,並在冰水浴中冷卻。在20分 鐘的時間内,將過氧化鈉(2 _ 4 2克,3 1毫莫耳)之水溶液 (水佔30毫升)慢慢滴入。再攪拌30分鐘之後,停止攪拌 ,然後將反應混合物加以過濾,並以甲醇加以冲洗。在 低壓下濃縮濾液。以濃度為1 Μ的磺酸鈉水溶液、水和二 乙醚來分別沖洗殘留物。在4 Q°C溫度下以真空方式來乾 燥産物,而産生一種白色的蠟(0.04克)。 核磁共振光譜(ds -丙酮):δ 2·4(π,2Η), 3 . 6 1 (π , 1 Η), 4.10(m2H),7.62(d,2H),7.98(Di,6H),8.13(ni,6H) 紅外線光譜(squash) : 1595,1500,1450,1150,1140,1085, 940,850,76(1 ,735,690 公分-1 例 11 由聚(苯撐硫化物)來製備硫錨鹽: f〇-4„ (I)
(請先閲筇背而之注意事項洱塡寫^一^) 經濟部十央標準杓Α工消仲合作社印^ 將聚(笨撐硫化物)U ) ( 1 . Q克,9 . 2 6毫Μ耳的硫化物 二苯基碘化六氟磷酸(4 . 3克,1 ϋ € Μ耳)和無水醋酸銅 (I I ) ( 0 . Q 8克,0 · 4 4毫樊耳)在1 4 0 - 1 6 Q-C的溫度下攪拌 17- 本紙尺度逍用中a S家標毕(CNS) T4規格(210X297公:¢) 81. 4. ]0,000張(11)
OiObb Λ 6 ___l$_C_ 五、發明説明(α) 四個小時。將此無色的溶液傾析。剩下的油質部分以二乙 _( 2 X 5 0毫升)、水(2 X 5 0毫升)加以沖洗,並使之溶解 於丙酮(2 5毫升)中。將此溶液滴入二乙醚 (2 0 0毫升)中, 形成棕色的沈澱物,將其收集後使之乾燥,而生成硫鐲鹽 (Ε ) ( 0 . 6 5 克,1 3 5:),熔點為 2 3 4 - 6。(〇 (分解)。 核磁共振光譜(ds -丙酮):δ 7.90(br.,ni) 紅外線光譜(溴化鉀 Η ) : 1 5 8 0 , 1 4 5 0 , 1 4 1 0 , 1 3 6 0 , 1 0 5 0 , 9 9 0 由硫_鹽來製備硫氧銳鹽: (請先閲讀背而之注意事項-nj-塡寫本頁)
經濟部屮央榀準而A工消赀合作杜印M _0fOlin 〇PF6-(ΠΙ) 將硫錨鹽(I I ) ( Q . 5克,0 . 9 3 6毫莫耳的硫_基圍)溶解 於甲醇(5 0毫升)中,並將溶液冷卻至0 °C ^將對甲苯磺 醯氯(1 · 2克,5 . 8 8奄Μ耳)和過氧化納(1 . 1克,1 5毫荑 耳)的水(1 5毫升)溶液加入混合物中。將混合物攪拌一 小時,然後加以濃縮以除去甲醇。以二氣甲烷(3 X 5 0毫 升)來萃取此産物,混合的有機層將被乾燥(M g S 0 4 )及 濃縮。將粗鹿物溶解於丙酮(2 0 Q荣升)中以使之纯化, 並且將此溶液加至六緘磷酸鉀(5克)的水(1 Q 0毫升)溶 液中。將此混合物予以冷卻,並收集其沈澱物及使之乾 -1 8 -
裝· 訂_ 線· 81. 4. 10,000張(Π) 本紙張尺度逍用中困國家標毕卬吒)174規格(210><297公;《:) u 〇5〇^>^ Λ 6 Π 6 五、發明説明(·?) 燥,而生成硫氧鎌鹽(I I I ) ( Ο · 1克,1 9 % ), 熔點 > 3 Ο Ο °C。 核磁共振光譜(ds -丙酮):8.20(br)和7.80(br) 紅外線光譜(溴化押片):1 5 Μ , 1 4 7 Ο , 1 4 4 Ο , 1 3 2 Ο , 1 1 6 Ο , 1070,84 0,750,720, S80 公分-1 例 12-18 將包含2, 2-雙(對縮水甘油基氣苯基)丙烷(1QG份重) 、如下表中所列之硫氧錨鹽(5份重)、及2份重做為敏 化劑的9 -甲基蒽之組成物塗佈於錫板上,使其形成厚度 為24徹米的薄膜。然後用兩種方式使其曝光而生成不易 剝落之塗佈層。第一種方式是單純的將其曝光於一個金 屬鹵素燈(50QQ瓦)下,距離為75公分,並且記錄下其不 再剝落時所需的時間。第二種方式則是將此薄膜在Ρ Γ i π a r c 型的儀器上,曝光於中度壓力的汞弧燈(每公分8 0瓦的 強度)下,距離為8公分,曝光時間為21.3米/分鐘。 形成不會剝落之塗佈層所需之次數將被記錄下來。 閲 讀 背 而 之 注 意 事 項 4 塡 % 才 M濟部屮央標準/(0A工消作合作社印¾ 81. 4. 10,000¾ (II) 本紙張尺度边用中® Η家標準(CNS)T4規格(2丨0X297公;«:) 五、發明説明Ο ?)
Λ 6 Η G 例 由何例製得之鹽類 時 間 通過次耖 12 1 0 5 分 鐘 3 13 3 1 5 分 鐘 14 14 5 1 5 分 鐘 7 15 7 1 0 分 鐘 7 16 8" — 19 17 9 2 5 分 鐘 12 18 10 — 16 *使用份量為10份重。 例 19-20 將包含2, 2-雙(對縮水甘油基氧苯基)丙烷(100份重) 和由例11所製之聚合硫氣銳鹽(3份重)、及含有或不含 9 -甲基恝做為敏化劑(1份重)之組成物塗於鍍銅的基板 上,使其形成厚度為24徹米的薄膜。將其曝光於一個金 屬鹵素燈(5QQQ瓦)下,距離為75公分,並且記錄下其不 再剝落時所裔的時間。 請 7t» 閱 讀 背 1¾ 之 注 意 事 項 孙 堝 % 本 經濟部+央伐準XJA工消作合作杜印製 例 化 合 物 時 間 19 镅類BI ,不含敏化劑 1 6 0秒 20 鹽類I ,含敏化劑 6 5秒 -20- 本紙張尺度边用中a Η家榀準(CNS)T4規ίΜ210χ297公;《:) 81. 4. 10,000張(II)
Claims (1)
- 六'申諳專利範团 第8 1 1 0 2 6 3 5號「硫氣銥鹽類j專利案 (82年3月修正) 1. —種三芳基硫氣絲鹽,其可在分子中包含一痼可聚合之 基團,或者是為聚合化合物的一部分。 2. 如申諳專利範圍第1項之三芳基硫氣銥鹽,其中的一脑 芳基偽連接於聚合鐽上。 . 3. 如申請專利範国第2項之三芳基硫氣銘®,其中聚合物 為含有苯基之聚合物.或者是為一種琛氣樹脂 4如申諳專利範国第2項之三芳基硫氧銥®,俟出現於主 鐽上25到75%的可能位置上,或者是為了寡浓物的端基 Ο 5..如申諳專利範圍第1項之三芳基硫氣絡鹽,其中一値芳 基被一個可聚合之基圃所取代。 6. 如申諳專利範圍第5項之三芳基硫氣絲鹽,其中的可聚 合基圃為包念乙烯的不飽和基團者,或者是一種1 , 2 -環氣化物基團。 7. 如申請專利範圍第1項之三芳基硫氣鉻鹽,其通式如下 (請先閱¾背面之注意事項再填寫本页} •装· 面化學式(I)所示:本纸張尺度適用中困國家標準(CNS)甲4規格(210x297公釐)_ A7 B7 C7 D7 六、申請專利範® 其中R包括一値(甲基.)丙烯酸_v乙烯醚、·烯两醚或·者 是琛氣基圃;X和Z可相同或相異,代表單價的取代基 ;p和<1可相同或相異,為零或者是小於六的整數。 8. 如申請專利範圍第1項之三芳基硫氣銥鹽,其中的硫氣 銥鹽基團傜在聚合物的主鐽上。 9. 如申諳專利範困第1項之三芳基硫氣銥鹽,其中陰離子 為 PF: 0 10 —種製備如申諳專利範圍第1項之三芳基硫氣銥鹽的方 法,其包括··將含反應性基團的芳基硫氣銥發,與可將 所需可聚合/基圃引入之化合物反應;或者是將含反應性 基面的芳基硫錢鹽,與可將所需可聚合基團引入之化合 物反應,然後再將硫銘鹽的部分氣化成硫銘鹽。 11 一種製備如申諳專利範圍第1項之三芳基硫氣銥鹽的方 法,其包括:將含反應性基團之聚合物與含有可與聚合 (請先Μ請背面之注意事項再填寫本页} 經濟部屮央標準局員工消費合作社印製 類銥物硫 .方氣 鹽氣合將 的被 銘硫化再 鹽傜 氣的氣後 銘鹽 硫應硫然 氣鉻 是對的, 硫硫 者相基物 基之 或其芳合 Q 芳團 類成二聚基三基 鹽換種的-銥之銘 鉻轉一分氣項硫 硫鹽與部硫 1 有 的銥物鹽成第具· 圃硫合鋒形圍中 〇 基將聚硫而範鐽鹽 之可族含化利主鈴 應亦香種氣專物氣 反要芳 一以請合硫 圃需將生加申聚的 基有是産分如在應 性如者而部備中對 應 ,或 ,的裂其相 反應;應基種 ,成 上反鹽反鉻 一法化 物12 本纸張尺度逋用中ΒΗ家櫺準(CNS)甲4規格(210x297公釐)· 六、申請專利範園 A7 B7 C7 D7 鹽1G 銥 每 氧 。中 硫劑其 基發 , 芳引鹽 三光錢 之性氧 項子硫 一 離基 任隈芳 項的三 9 料之 到材項 1 合13 第聚第 圍可圍 範子範 利雔利 專陽專 諳為諳 申做申 如傜如 1314 有 含 中 料 材 合 聚 可 的 5 重 〇 份鹽 到 0 氧 硫 的 S 重 份 (請先«I讀背面之注意事項再填商本頁} .c. .裝· 經濟部中央樣準局貝工消费合作社印製 本纸a尺度適用中因a家棵準(CNS)甲4規格(210x297公釐r
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GB919108132A GB9108132D0 (en) | 1991-04-13 | 1991-04-13 | Sulphoxonium salts |
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JP (1) | JPH05178819A (zh) |
BR (1) | BR9201303A (zh) |
CA (1) | CA2065776A1 (zh) |
GB (1) | GB9108132D0 (zh) |
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AU2001296651A1 (en) * | 2000-10-06 | 2002-04-15 | Robert C. Corcoran | Resin and its use in converting morphine to codeine |
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US4339567A (en) * | 1980-03-07 | 1982-07-13 | Ciba-Geigy Corporation | Photopolymerization by means of sulphoxonium salts |
DE3902114A1 (de) * | 1989-01-25 | 1990-08-02 | Basf Ag | Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare sulfoniumsalze und verfahren zu deren herstellung |
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1992
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GB9108132D0 (en) | 1991-06-05 |
CA2065776A1 (en) | 1992-10-14 |
BR9201303A (pt) | 1992-12-01 |
EP0510839A1 (en) | 1992-10-28 |
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