CN103980181B - 含有1-甲基-2-苯基吲哚骨架的三芳基锍盐及其制备方法 - Google Patents
含有1-甲基-2-苯基吲哚骨架的三芳基锍盐及其制备方法 Download PDFInfo
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- CN103980181B CN103980181B CN201410238326.8A CN201410238326A CN103980181B CN 103980181 B CN103980181 B CN 103980181B CN 201410238326 A CN201410238326 A CN 201410238326A CN 103980181 B CN103980181 B CN 103980181B
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- Prior art keywords
- methyl
- phenylindone
- skeleton
- preparation
- triarylsulfonium salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000005409 triarylsulfonium group Chemical group 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 15
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 claims abstract description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000002475 indoles Chemical class 0.000 claims description 14
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 10
- UGVWZFIIQPTOBR-UHFFFAOYSA-N fluoroform sulfane Chemical compound S.FC(F)F UGVWZFIIQPTOBR-UHFFFAOYSA-N 0.000 claims description 10
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 9
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 5
- 239000012955 diaryliodonium Substances 0.000 claims description 5
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 5
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 15
- -1 aromatic sulfonium salt compound Chemical class 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 5
- 239000003973 paint Substances 0.000 abstract description 5
- 239000003999 initiator Substances 0.000 abstract description 4
- 150000001768 cations Chemical class 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000005357 flat glass Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960004418 trolamine Drugs 0.000 description 3
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical group C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- ODVMNRPMODUJSW-UHFFFAOYSA-N C(F)(F)F.[I].C1(=CC=CC=C1)C1=CC=CC=C1 Chemical group C(F)(F)F.[I].C1(=CC=CC=C1)C1=CC=CC=C1 ODVMNRPMODUJSW-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 0 CCC(*(C)c1c2cccc1)=C2N=CO Chemical compound CCC(*(C)c1c2cccc1)=C2N=CO 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- DZHAKMZHPZQEIN-UHFFFAOYSA-N [I].FC(F)F Chemical compound [I].FC(F)F DZHAKMZHPZQEIN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
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CN201410238326.8A CN103980181B (zh) | 2014-05-30 | 2014-05-30 | 含有1-甲基-2-苯基吲哚骨架的三芳基锍盐及其制备方法 |
Applications Claiming Priority (1)
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CN201410238326.8A CN103980181B (zh) | 2014-05-30 | 2014-05-30 | 含有1-甲基-2-苯基吲哚骨架的三芳基锍盐及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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CN103980181A CN103980181A (zh) | 2014-08-13 |
CN103980181B true CN103980181B (zh) | 2016-01-20 |
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CN201410238326.8A Expired - Fee Related CN103980181B (zh) | 2014-05-30 | 2014-05-30 | 含有1-甲基-2-苯基吲哚骨架的三芳基锍盐及其制备方法 |
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CN110357798B (zh) * | 2019-06-12 | 2021-01-29 | 中国石油天然气股份有限公司 | 一种从石油基质中分离锍盐的方法 |
CN111153849B (zh) * | 2019-12-19 | 2021-03-26 | 南京林业大学 | 一种2-吲哚甲醇在水相反应体系中合成c3位硫醚化吲哚衍生物的方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1244198A (zh) * | 1997-01-22 | 2000-02-09 | 西巴特殊化学品控股有限公司 | 基于α-氨基酮的可光活化的含氮碱 |
US20120251948A1 (en) * | 2011-03-28 | 2012-10-04 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, and actinic ray-sensitive or radiation-sensitive film and pattern forming method using the same composition |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012137686A (ja) * | 2010-12-27 | 2012-07-19 | Fujifilm Corp | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜及びパターン形成方法 |
-
2014
- 2014-05-30 CN CN201410238326.8A patent/CN103980181B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1244198A (zh) * | 1997-01-22 | 2000-02-09 | 西巴特殊化学品控股有限公司 | 基于α-氨基酮的可光活化的含氮碱 |
US20120251948A1 (en) * | 2011-03-28 | 2012-10-04 | Fujifilm Corporation | Actinic ray-sensitive or radiation-sensitive resin composition, and actinic ray-sensitive or radiation-sensitive film and pattern forming method using the same composition |
Non-Patent Citations (3)
Title |
---|
A Practical Regioselective Synthesis of Alkylthio- or Arylthioindoles without the Use of Smelly Compounds Such as Thiols;Toshihiko Hamashima,等;《Chemical & Pharmaceutical Bulletin》;20121206;第61卷(第3期);第292-303页 * |
Indole- and pyrrolesulfonium ylides;Klaus Hartke,等;《Tetrahedron》;19881231;第44卷(第11期);第3261-3270页 * |
Synthesis of methylthio-substituted heterocycles using the complex of trifluoromethanesulfonic anhydride with dimethyl sulfide;N.E.Shevchenko,等;《Chemistry of Heterocyclic Compounds》;20001231;第36卷(第2期);第137-138页反应式、第139页表1、第140页方案、第140-141页实验部分 * |
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Publication number | Publication date |
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CN103980181A (zh) | 2014-08-13 |
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Effective date of registration: 20170830 Address after: 030600, No. 8, Yuci Industrial Park, Shanxi, Jinzhong Patentee after: SHANXI LIANGLONG PAINT Co.,Ltd. Address before: 030006 Taiyuan, Xiaodian District, Shanxi City Road, No. 92 Patentee before: SHANXI University |
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Inventor after: Wang Xiaohong Inventor after: Hou Pengxiang Inventor before: Zhang Bianxiang Inventor before: Tian Huaidong Inventor before: Chen Kai |
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