CN110105315A - Oxime ester compound and its preparation method and application containing aryl thioethers furans or aryl thioethers thiophene - Google Patents
Oxime ester compound and its preparation method and application containing aryl thioethers furans or aryl thioethers thiophene Download PDFInfo
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- CN110105315A CN110105315A CN201910361462.9A CN201910361462A CN110105315A CN 110105315 A CN110105315 A CN 110105315A CN 201910361462 A CN201910361462 A CN 201910361462A CN 110105315 A CN110105315 A CN 110105315A
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- China
- Prior art keywords
- aryl thioethers
- aryl
- alkyl
- thiophene
- thioethers
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- -1 Oxime ester compound Chemical class 0.000 title claims abstract description 70
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 150000004832 aryl thioethers Chemical class 0.000 title claims abstract description 34
- 229930192474 thiophene Natural products 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 16
- GYICYQJEVCIYJY-UHFFFAOYSA-N thiophen-1-ylidenemethanone Chemical class O=C=S1C=CC=C1 GYICYQJEVCIYJY-UHFFFAOYSA-N 0.000 claims description 14
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 13
- 238000003847 radiation curing Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002923 oximes Chemical class 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002241 furanones Chemical class 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 3
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000862 absorption spectrum Methods 0.000 abstract description 2
- 150000002240 furans Chemical class 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 description 30
- 238000004896 high resolution mass spectrometry Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000000016 photochemical curing Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920006305 unsaturated polyester Polymers 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002975 chemoattractant Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HFXKQSZZZPGLKQ-UHFFFAOYSA-N cyclopentamine Chemical compound CNC(C)CC1CCCC1 HFXKQSZZZPGLKQ-UHFFFAOYSA-N 0.000 description 1
- 229960003263 cyclopentamine Drugs 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/64—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of oxime ester compound and its preparation method and application containing aryl thioethers furans or aryl thioethers thiophene, the R in the oxime ester compound1、R2、R3、R4、R5、R6And R7It is respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO2R、NRR’、CH2OH、CH2OR、CH2OCOR、CH2SR、CH2SCOR and CH2NRR ', R8And R9It is respectively selected from C1‑C20Straight chained alkyl or C1‑C20Branched alkyl, C3‑C12Naphthenic base, cycloalkyl-alkyl, cycloheteroalkyl alkyl, C6‑C12Aryl, alkylaryl；The present invention by introducing heterocycle in the molecular structure, including furan nucleus and thiphene ring, heteroatomic introducing further provides lone pair electrons, makes the further red shift compared with phenyl ring of the absorption spectrum of this kind of molecule, more matches with the launch wavelength for the LED light source being commercialized at present.
Description
Technical field
The invention belongs to new material organic chemicals technical fields, and in particular to a kind of oxime ester containing aryl thioethers heterocycle
The compound of type structure, oxime ester compound and its preparation more specifically containing aryl thioethers furans or aryl thioethers thiophene
Methods and applications.
Background technique
Photoinitiator compound is a kind of important Fine Organic Chemical product material.With emitting ultraviolet light or visible light
Mercury lamp or LED (i.e. Light-Emitting Diode) are the radiation curing technology field of light source, can be given birth under light radiation parameter
Photoinitiator compound at free radical activity species is the key that induce the system of unsaturation containing alkene to carry out efficient photopolymerization reaction
One of species, therefore be important radiation curable formulation component.Photocuring has energy conservation and environmental protection, efficiently quick and time-space
Many advantages, such as controllable, is widely used to the new high-tech products such as the traditional fields such as coating and printing ink, adhesive and 3D printing
In.Photosensitive resin formula for photocuring usually contains photoinitiator, reactive diluent, oligomer and various auxiliary agents, wherein
Photoinitiator is the key component of photocurable formulation, and activity directly affects photo-curing rate, curing degree and end product
Performance.
Compared with traditional ultraviolet light solidification, there is energy using light emitting diode (LED) as the solidification of the LED light of light source
Utilization rate is high, fuel factor is small, does not generate the remarkable advantages such as ozone.Traditional photoinitiator is mainly used for the shorter UV light of wavelength
Change, it is difficult to match with LED light source, so developing a system by the structure activity study of reasonable MOLECULE DESIGN and system
Efficient LED light initiator is arranged with very big application prospect.
Aryl oxime ester or aryl ketones oxime ester are the very extensive photoinitiators of a kind of purposes, and famous oxime esters cause
Agent OXE-01 and OXE-02 be exactly among these classic representative business chemoattractant molecule, molecular structure it is as follows:
Challenge in view of the above technology, invention it is a kind of it is sensitive to LED light source, have in curing field high photosensitivity,
Stability is high and easily prepared photoinitiator is still very important, in addition, such initiator synthesis step should have
Have the advantages that easy, cost is relatively low and synthesis process is environmentally friendly, the three wastes are few.As people realize environmental protection, production safety
And all kinds of requirements of labour protection continuous improvement and light polymerization technique continuous development, the low energy consumption such as LED, LDI, high security and
The exposure lamp source of environmental protection becomes a kind of trend of art technology application and development.
Summary of the invention
Aiming at the shortcomings in the prior art, primary and foremost purpose of the invention is to provide a kind of oxime ester containing aryl thioethers furans
Class compound or oxime ester compound containing aryl thioethers thiophene.
A second object of the present invention is to provide a kind of preparation methods of above-mentioned oxime ester compound.
Third object of the present invention is to provide the purposes of above-mentioned oxime ester compound.
In order to achieve the above objectives, solution of the invention is:
A kind of oxime ester compound containing aryl thioethers furans or aryl thioethers thiophene, general formula are as follows:
Wherein, R1、R2、R3、R4、R5、R6And R7It is respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO2R、NRR’、
CH2OH、CH2OR、CH2OCOR、CH2SR、CH2SCOR and CH2One or more of NRR '.
R and R ' are respectively selected from C1-C24Straight chained alkyl, C1-C24Branched alkyl and-C6-C24One or more of aryl, R and
R ' may be the same or different.
Specifically, hydrogen atom can be replaced to form fluorocarbon chain structure with fluorine atom in R and R ' structure；It can in R and R ' structure
To contain 1-6 discrete S, O, N element, is i.e. includes not only carbochain in R and R ' structure, miscellaneous original can also be introduced in carbochain
Son is no longer that only pure carbochain can contain hetero atom as substituent group to form such as C-C-O-C-C, C-C-S-C-C etc.
Carbochain can also be used as substituent group.
The ring system structure that a 3-6 member can be formed when R and R ' are existed simultaneously in NRR ', such as ring butylamine base, cyclopentamine base,
Cyclohexylamino etc..
R8And R9It is respectively selected from C1-C20Straight chained alkyl, C1-C20Branched alkyl, C3-C12Naphthenic base, cycloalkyl-alkyl, ring are miscellaneous
Alkyl-alkyl, C6-C12One or more of aryl and alkylaryl；R8And R9C can also be formed by being connected6-C24Naphthenic base.
Further, cycloalkyl-alkyl is selected fromWherein, x=1-5, y=1-6.
Further, cycloheteroalkyl alkyl is selected fromWherein, x=1-5, y=1-6, z are in S, O, N
More than one.
A kind of preparation method of the above-mentioned oxime ester compound containing aryl thioethers furans or aryl thioethers thiophene, packet
Include following steps:
(1), contain R1、R2、R3、R4、R5The furanone of substituted aryl thiophenol and bromo or the thienone of bromo are in alkali item
It is reacted under part, obtains aryl thioethers substituted furanone (I-a) or aryl thioethers substituted thiophene ketone (I-a):
(2), aryl thioethers substituted furanone (I-a) or aryl thioethers substituted thiophene ketone (I-a) are at alkaline (preferably KOH)
Under the conditions of and hydroxylamine hydrochloride reacted, obtain oxime product (I-b):
(3), oxime product (I-b) is reacted under alkalinity effect with acyl chlorides or acid anhydrides, is obtained containing aryl thioethers furan
It mutters or the oxime ester compound of aryl thioethers thiophene:
Further, R1、R2、R3、R4、R5、R6And R7It is respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO2R、NRR’、
CH2OH、CH2OR、CH2OCOR、CH2SR、CH2SCOR and CH2One or more of NRR '.
Wherein, R and R ' are respectively selected from C1-C24Straight chained alkyl, C1-C24Branched alkyl and-C6-C24One of aryl with
On.
R8And R9It is respectively selected from C1-C20Straight chained alkyl, C1-C20Branched alkyl, C3-C12Naphthenic base, cycloalkyl-alkyl, ring are miscellaneous
Alkyl-alkyl, C6-C12One or more of aryl and alkylaryl；R8And R9C can also be formed by being connected6-C24Naphthenic base.
Further, cycloalkyl-alkyl is selected fromWherein, x=1-5, y=1-6.
Further, cycloheteroalkyl alkyl is selected fromWherein, x=1-5, y=1-6, z are in S, O, N
More than one.
A kind of above-mentioned oxime ester compound for containing aryl thioethers furans or aryl thioethers thiophene is as radiation curing light
The purposes of quick initiator.Specifically, the purposes as photoinitiator or other functional additive ingredients, and in chemical synthesis
The middle purposes as intermediate or raw material or reagent.
Further, the light source of radiation curing photoinitiator is selected from one or more of ultraviolet light and visible light.
Further, the light source of radiation curing photoinitiator be selected from can emitting ultraviolet light, the mercury lamp of visible light, LED
One or more of light source, LDI light source.
Further, radiation curing photoinitiator includes that 0.01-30 parts by weight contain aryl thioethers furans or aryl sulphur
The oxime ester compound of ether thiophene and 100 parts by weight contain ethylene linkage (C=C) unsaturated compound.
Further, radiation curing photoinitiator includes that 0.5-10 parts by weight contain aryl thioethers furans or aryl thioethers
The oxime ester compound of thiophene and 100 parts by weight contain ethylene linkage (C=C) unsaturated compound.
In fact, radiation curing photoinitiator is in addition to including the oxime ester containing aryl thioethers furans or aryl thioethers thiophene
Class compound and containing except ethylene linkage (C=C) unsaturated compound, can also containing add according to actual needs inorganic filler,
Any components such as organic filler, colorant, other additives and solvent.
Wherein, colorant is selected from pigments or dyes.
Other additives include ultraviolet absorbing agent, light stabilizer, fire retardant, levelling agent or defoaming agent.
Specific step is as follows: (1) pressing monomer and resin: photoinitiator: the mass ratio 100:0.5-1:0-4.5 proportion of auxiliary agent
Raw material；(2) stirring dissolves it sufficiently；(3) polymerization system is irradiated with the light source of different wave length or different light intensity；It (4) can be with
Pass through the Changeement polymerisation conversion of its characteristic peak with online infrared method；Wherein: the light source in step (3) can be mercury lamp
(high pressure, middle pressure and low pressure) and launch wavelength are the LEDs of 365-425nm, LDI light source.
Further, unsaturated compound containing ethylene linkage refer to compound that ethylene linkage is crosslinked by Raolical polymerizable or
Mixture.
Further, unsaturated compound containing ethylene linkage be selected from monomer, oligomer or prepolymer or three mixture or
Copolymer or the water-borne dispersions of three.
The monomer such as polymerisable monomer containing ethylene linkage of suitable free radical polymerization, including but not limited to (methyl) acrylic acid
Ester, methacrylaldehyde, alkene, conjugated diolefin, styrene, maleic anhydride, fumaric acid anhydride, vinyl acetate, vinyl pyrrolidone,
Vinyl imidazole, (methyl) acrylic acid, (methyl) acrylic acid derivative such as (methyl) acrylamide, vinyl halide and Asia
Vinyl halide etc..
Suitable prepolymer containing ethylene linkage and oligomer include but is not limited to (methyl) propylene of (methyl) acryloyl functional group
Acid copolymer, polyurethane formic acid esters (methyl) acrylate, polyester (methyl) acrylate, unsaturated polyester (UP), polyethers (methyl)
The water solubility of acrylate, siloxanes (methyl) acrylate, epoxy resin (methyl) acrylate etc. and above-mentioned substance or
The analog of water dispersible.
It is above-mentioned either to contain alkene monomer or oligomer, prepolymer or copolymer, to this profession working technical staff
Speech, be all it is well known, be not particularly limited.
The exemplary compounds for meeting logical formula (I) structure are listed below:
By adopting the above scheme, the beneficial effects of the present invention are:
Oxime ester compound containing aryl thioethers furans of the invention or the oxime esters containing aryl thioethers thiophene
It closes object to apply as radiation curing photoinitiator and in radiation curable formulation product, can especially swash in UV-Vis-LED
The applications such as the photocureable coating or ink of hair.It is excellent as one kind by the oxime ester compound of representative of OXE-01 and OXE-02
Good radical photoinitiator has very good light-initiated property, and the present invention passes through introduces heterocycle in the molecular structure,
Including furan nucleus and thiphene ring, heteroatomic introducing further provides lone pair electrons, makes the absorption spectrum and benzene of this kind of molecule
Ring compares further red shift, more matches with the launch wavelength for the LED light source being commercialized at present.In addition, this kind of molecule synthesis letter
It is single, environmentally protective, the three wastes are lower, be a kind of very promising photoinitiator type.
Detailed description of the invention
Fig. 1 is the general structure of the oxime ester compound of the invention containing aryl thioethers furans or aryl thioethers thiophene.
Specific embodiment
As shown in Figure 1, the present invention provides a kind of oxime esters chemical combination containing aryl thioethers furans or aryl thioethers thiophene
Object, and its preparation method and application.
The present invention is further illustrated with reference to embodiments.
Embodiment 1:
Intermediate: the preparation process of aryl thioethers substituted furanone or aryl thioethers substituted thiophene ketone:
Wherein, in N2Under protection, by the furanone of bromo or thienone (10mmol), the cuprous oxide of bromo
(5mmol) and potassium hydroxide (10mmol) are distributed to dimethylformamide (DMF, 0.2mol/L), are slowly added to various substituted
Aryl thiophenol (10mmol) is heated to 100-150 DEG C, reacts 3-10h, is cooled to room temperature, is neutralized with 6N (equivalent concentration) hydrochloric acid,
Methylene chloride extraction, anhydrous sodium sulfate is dry, is purified after solvent evaporated with ethyl alcohol recrystallization or silica gel column chromatography.It obtains
Target product.According to the difference of raw material, yield is in 50-85%.
Embodiment 2: the preparation process of the oxime ester compound (I) -1 containing aryl thioethers furans of the present embodiment:
Benzenethiol (10mmol) is slowly added into 1- acetyl group -4- bromine furans (10mmol), cuprous oxide (5mmol), hydrogen
Potassium oxide (10mmol) is scattered in the DMF of 50mL, under nitrogen atmosphere, is heated to 130 DEG C, is stirred to react 3h, be cooled to room temperature
After be added in 50mL water, adjusted with the hydrochloric acid of 6N (equivalent concentration) to neutrality, after methylene chloride extraction, ethyl alcohol recrystallization is produced
Rate 84%.
The ketone of previous step preparation is dissolved in dehydrated alcohol (0.2mol/L), and 1.5 equivalent hydroxylamine hydrochlorides and 2 equivalent hydrogen-oxygens are added
Change sodium, be heated to reflux 5h, is concentrated, is poured into deionized water, filters the solid i.e. product of precipitation, be not required to purify, it is direct after dry
Carry out the next step；In darkroom, in N2Under gas shielded, (5mmol) oxime, the anhydrous dichloromethane of 50mL are successively put into three-necked flask
Alkane is added the triethylamine of 10mmol after stirring 5min at room temperature, then 5mmol acetic anhydride is added dropwise, and about 30min is added dropwise, and continues
Stir 2h.50mL deionized water, methylene chloride extraction, respectively with the HCl of 2mol/L, 5% NaHCO is added in reaction system3
Aqueous solution is washed, and adjusts pH to neutrality；Anhydrous Na SO4Dry, vacuum distillation removes solvent；Silica gel chromatography is crossed, eluant, eluent
Polarity selects PE/EA=2:1, finally obtains light yellow solid Compound, gross production rate 88%.HR-MS(C14H13NO3S): m/e:
275.0616；Experimental result: 276.1693 (M+H+)。
Embodiment 3: the preparation of the oxime ester compound containing aryl thioethers furans or aryl thioethers thiophene of the present embodiment
Process:
(1) gained aryl sulphur substituted furanone or aryl thioethers substituted thiophene ketone are dissolved in appropriate dehydrated alcohol, are added
A small amount of water and hydroxylamine hydrochloride (1.5mol equivalent) and solid NaOH (2mol equivalent), are heated to reflux 5h, are poured into deionized water, take out
The precipitating being precipitated is filtered to get intermediate oxime product；
(2) synthesis of target product: in darkroom, in N2Under protection, successively investment (5mmol) oxime is produced in three-necked flask
Object, 50mL anhydrous methylene chloride are added the triethylamine of 10mmol after stirring 5min at room temperature, then 5mmol acid anhydrides or acyl are added dropwise
Chlorine, about 30min are added dropwise, and continue to stir 2h.50mL deionized water is added in reaction system, methylene chloride extraction is used respectively
The HCl of 2mol/L, 5% NaHCO3Aqueous solution is washed, and adjusts pH to neutrality；Anhydrous Na SO4Dry, vacuum distillation removes solvent；Cross silicon
The polarity of rubber column gel column chromatogram purification, eluant, eluent selects PE/EA=2:1, finally obtains solid product, gross production rate 70-90%.
The characterization of series:
(I) -2, gross production rate 80%, HR-MS (C15H15NO3S): m/e:289.0773；Experimental result: 290.0860 (M+H+)。
(I) -3, gross production rate 83%, HR-MS (C16H16NO3S): m/e:302.0851；Experimental result: 303.1939 (M+H+)。
(I) -4, gross production rate 81%, HR-MS (C17H19NO3S): m/e:317.1086；Experimental result: 318.1164 (M+H+)。
(I) -5, gross production rate 77%, HR-MS (C18H21NO3S): m/e:331.1242；Experimental result: 332.1320 (M+H+)。
(I) -6, gross production rate 75%, HR-MS (C19H22NO3S): m/e:344.1320；Experimental result: 345.1407 (M+H+)。
(I) -7, gross production rate 82%, HR-MS (C19H21NO3S): m/e:343.1242；Experimental result: 344.1330 (M+H+)。
(I) -8, gross production rate 74%, HR-MS (C19H15NO3S): m/e:337.0773；Experimental result: 338.0860 (M+H+)。
(I) -9, gross production rate 83%, HR-MS (C20H24NO3S): m/e:358.1477；Experimental result: 359.1564 (M+H+)。
(I) -10, gross production rate 75%, HR-MS (C22H28NO3S): m/e:386.1790；Experimental result: 387.1866 (M+H+)。
(I) -11, gross production rate 82%, HR-MS (C23H30NO3S): m/e:400.1946；Experimental result: 401.2023 (M+H+)。
(I) -12, gross production rate 81%, HR-MS (C25H26NO3S): m/e:420.1633；Experimental result: 421.1710 (M+H+)。
(I) -13, gross production rate 80%, HR-MS (C25H28NO3S): m/e:422.1790；Experimental result: 423.1877 (M+H+)。
(I) -14, gross production rate 76%, HR-MS (C25H26NO3S): m/e:420.1633；Experimental result: 421.1711 (M+H+)。
(I) -15, gross production rate 80%, HR-MS (C25H26NO3S): m/e:420.1633；Experimental result: 421.1710 (M+H+)。
(I) -16, gross production rate 74%, HR-MS (C26H28NO3S): m/e:434.1790；Experimental result: 435.166 (M+H+)。
(I) -17, gross production rate 75%, HR-MS (C18H21NO2S2): m/e:347.1014；Experimental result: 348.1092 (M+H+)。
(I) -18, gross production rate 77%, HR-MS (C19H22NO2S2): m/e:360.1092；Experimental result: 361.1168 (M+H+)。
(I) -19, gross production rate 80%, HR-MS (C19H21NO2S2): m/e:359.1014；Experimental result: 360.1091 (M+H+)。
(I) -20, gross production rate 81%, HR-MS (C19H15NO2S2): m/e:353.0544；Experimental result: 354.0622 (M+H+)。
(I) -21, gross production rate 84%, HR-MS (C20H24NO2S2): m/e:374.1248；Experimental result: 375.1335 (M+H+)。
(I) -22, gross production rate 78%, HR-MS (C22H28NO2S2): m/e:402.1561；Experimental result: 403.1638 (M+H+)。
(I) -23, gross production rate 81%, HR-MS (C23H30NO2S2): m/e:416.1718；Experimental result: 417.1796 (M+H+)。
(I) -24, gross production rate 76%, HR-MS (C25H26NO2S2): m/e:436.1405；Experimental result: 437.1482 (M+H+)。
(I) -25, gross production rate 79%, HR-MS (C24H24NO2S2): m/e:422.1248；Experimental result: 423.1335 (M+H+)。
(I) -26, gross production rate 77%, HR-MS (C25H26NO2S2): m/e:436.1405；Experimental result: 437.1482 (M+H+)。
(I) -27, gross production rate 81%, HR-MS (C25H26NO2S2): m/e:436.1405；Experimental result: 437.1483 (M+H+)。
(I) -28, gross production rate 75%, HR-MS (C26H28NO2S2): m/e:450.1561；Experimental result: 451.1639 (M+H+)。
<experiment>
It is tested as follows respectively with the product of above-described embodiment.
<experiment 1>
Film polymer reaction:
Photocuring test sample: epoxy acrylate: 28 parts is prepared according to following weight percent；Polyester acrylic
Ester: 32 parts；Hexanediyl ester: 6 parts；Pentaerythritol triacrylate: 24 parts；Titanium dioxide dyestuff: 16 parts；It chooses
The photoinitiator of embodiment: 4 parts.
It is coated on white ABS substrate after taking part said mixture to be fully ground uniformly, forms about 20 μm under air
Figure layer.It is irradiated at sample 2cm with 365nm and 385nm LED solidity test machine (and light is with Sheng, Guangzhou), transmits belt speed
Degree is 20m/min.Finger pressure scrapes hair and determines that situation is fully cured in coating.Photoinitiator causes film layer in above-described embodiment compound
It is fully cured, especially R8More excellent initiation performance is shown when volume is larger.
<experiment 2>
Thick film polymerization reaction:
Formula is the same as experiment 1.
It is coated on after taking part said mixture to be fully ground on white ABS substrate, forms about 200 μm of figure under air
Layer.It is irradiated at sample 2cm with 365nm and 385nm LED solidity test machine (and light is with Sheng, Guangzhou), conveyor belt speed is
10m/min.Pressure scrapes hair and determines that situation is fully cured in coating.Molecular structure in above-described embodiment (2), particular with larger
R8The photoinitiator of substituent group causes film layer and is fully cured, it is shown that good Photoinitiation Property.
The above-mentioned description to embodiment is that this hair can be understood and used for the ease of those skilled in the art
It is bright.Those skilled in the art obviously readily can make various modifications to these embodiments, and described herein one
As principle be applied in other embodiments, without having to go through creative labor.Therefore, the present invention is not limited to the above embodiments.
Those skilled in the art's principle according to the present invention, not departing from improvement that scope of the invention is made and modification all should be at this
Within the protection scope of invention.
Claims (9)
1. a kind of oxime ester compound containing aryl thioethers furans or aryl thioethers thiophene, it is characterised in that: its general formula is as follows:
Wherein, R1、R2、R3、R4、R5、R6And R7It is respectively selected from hydrogen, halogen atom, R, OR, SR, SOR, SO2R、NRR’、CH2OH、
CH2OR、CH2OCOR、CH2SR、CH2SCOR and CH2One or more of NRR '；
R and R ' are respectively selected from C1-C24Straight chained alkyl, C1-C24Branched alkyl and-C6-C24One or more of aryl；
R8And R9It is respectively selected from C1-C20Straight chained alkyl, C1-C20Branched alkyl, C3-C12Naphthenic base, cycloalkyl-alkyl, cycloheteroalkyl
Alkyl, C6-C12One or more of aryl and alkylaryl.
2. the oxime ester compound according to claim 1 containing aryl thioethers furans or aryl thioethers thiophene, feature
Be: the cycloalkyl-alkyl is selected fromWherein, x=1-5, y=1-6；
Preferably, the cycloheteroalkyl alkyl is selected fromWherein, x=1-5, y=1-6, z in S, O, N one
Kind or more.
3. a kind of system of the oxime ester compound according to claim 1 containing aryl thioethers furans or aryl thioethers thiophene
Preparation Method, it is characterised in that: it includes the following steps:
(1), contain R1、R2、R3、R4、R5The thienone of the furanone of substituted aryl thiophenol and bromo or bromo is under alkaline conditions
Reaction, obtains aryl thioethers substituted furanone (I-a) or aryl thioethers substituted thiophene ketone (I-a):
(2), the aryl thioethers substituted furanone (I-a) or the aryl thioethers substituted thiophene ketone (I-a) are in alkaline condition
Lower and hydroxylamine hydrochloride is reacted, and oxime product (I-b) is obtained:
(3), the oxime product (I-b) is reacted under alkalinity effect with acyl chlorides or acid anhydrides, obtains containing aryl thioethers furan
It mutters or the oxime ester compound of aryl thioethers thiophene:
4. preparation method according to claim 3, it is characterised in that: R1、R2、R3、R4、R5、R6And R7It is respectively selected from hydrogen, halogen
Plain atom, R, OR, SR, SOR, SO2R、NRR’、CH2OH、CH2OR、CH2OCOR、CH2SR、CH2SCOR and CH2One of NRR '
More than；
Wherein, R and R ' are respectively selected from C1-C24Straight chained alkyl, C1-C24Branched alkyl and-C6-C24One or more of aryl；
R8And R9It is respectively selected from C1-C20Straight chained alkyl, C1-C20Branched alkyl, C3-C12Naphthenic base, cycloalkyl-alkyl, cycloheteroalkyl
Alkyl, C6-C12One or more of aryl and alkylaryl.
5. the preparation method according to claim 4, it is characterised in that: the cycloalkyl-alkyl is selected fromIts
In, x=1-5, y=1-6；
Preferably, the cycloheteroalkyl alkyl is selected fromWherein, x=1-5, y=1-6, z in S, O, N one
Kind or more.
6. one kind contains the oxime ester compound of aryl thioethers furans or aryl thioethers thiophene as spoke as described in claim 1
Penetrate the purposes for solidifying photoinitiator.
7. purposes according to claim 6, it is characterised in that: the light source of the radiation curing photoinitiator is selected from ultraviolet
One or more of light and visible light.
8. purposes according to claim 6, it is characterised in that: the radiation curing photoinitiator includes 0.01-30 weight
Measure oxime ester compound of the part containing aryl thioethers furans or aryl thioethers thiophene and 100 the parts by weight chemical combination of unsaturation containing ethylene linkage
Object；
Preferably, the radiation curing photoinitiator includes that 0.5-10 parts by weight contain aryl thioethers furans or aryl thioethers thiophene
The oxime ester compound of pheno and 100 parts by weight unsaturated compounds containing ethylene linkage.
9. purposes according to claim 8, it is characterised in that: the unsaturated compound containing ethylene linkage refers to that ethylene linkage passes through certainly
The compound or mixture being crosslinked by base polymerization reaction；
Preferably, the unsaturated compound containing ethylene linkage is selected from the mixture or total of monomer, oligomer or prepolymer or three
Polymers or the water-borne dispersions of three.
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