JP2018177696A - ベンゾトリアゾール誘導体化合物 - Google Patents
ベンゾトリアゾール誘導体化合物 Download PDFInfo
- Publication number
- JP2018177696A JP2018177696A JP2017079707A JP2017079707A JP2018177696A JP 2018177696 A JP2018177696 A JP 2018177696A JP 2017079707 A JP2017079707 A JP 2017079707A JP 2017079707 A JP2017079707 A JP 2017079707A JP 2018177696 A JP2018177696 A JP 2018177696A
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- Prior art keywords
- group
- carbon atoms
- alkyl
- benzotriazole
- light
- 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.)
- Granted
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- -1 Benzotriazole derivative compounds Chemical class 0.000 title claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 239000006096 absorbing agent Substances 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000011342 resin composition Substances 0.000 claims description 6
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 238000010521 absorption reaction Methods 0.000 description 18
- 238000005259 measurement Methods 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000005562 fading Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 210000001508 eye Anatomy 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 0 *c1cc(O*)cc(*2*=C3C=CC(C(Cl)=O)=CC23)c1O Chemical compound *c1cc(O*)cc(*2*=C3C=CC(C(Cl)=O)=CC23)c1O 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VIBDNSSTORKKOI-UHFFFAOYSA-N 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylic acid Chemical compound C(=O)(O)C1=CC=2C(=NN(N2)C2=C(C(=CC(=C2)OC)C(C)(C)C)O)C=C1 VIBDNSSTORKKOI-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 150000001565 benzotriazoles Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920006027 ternary co-polymer Polymers 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- XPKALWPNNRWDOC-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-(2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylate Chemical compound C(=C)(C)C(=O)OCCOC(=O)C=1C=CC2=NN(C3=C(O)C=CC(OC)=C3)N=C2C=1 XPKALWPNNRWDOC-UHFFFAOYSA-N 0.000 description 1
- QIBFWSGGHOOHNT-UHFFFAOYSA-N 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)-1-oxidobenzotriazol-1-ium-5-carboxylic acid Chemical compound C(=O)(O)C1=CC=2C(=[N+](N(N=2)C2=C(C(=CC(=C2)OC)C(C)(C)C)O)[O-])C=C1 QIBFWSGGHOOHNT-UHFFFAOYSA-N 0.000 description 1
- GFYPTVHEXDEREA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-tert-butyl-4-methoxyphenol Chemical compound CC(C)(C)C1=C(C(=CC(=C1)OC)N2N=C3C=CC=CC3=N2)O GFYPTVHEXDEREA-UHFFFAOYSA-N 0.000 description 1
- VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 description 1
- XBBAUTKOTJMTMN-UHFFFAOYSA-N 2-ethylhexyl 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylate Chemical compound C(C)(C)(C)C=1C(=C(C=C(C=1)OC)N1N=C2C(=N1)C=CC(=C2)C(=O)OCC(CCCC)CC)O XBBAUTKOTJMTMN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- FKZSJNUXYCEZQE-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylate Chemical compound C(C)(C)(C)C=1C(=C(C=C(C=1)OC)N1N=C2C(=N1)C=CC(=C2)C(=O)OCCOC(C=C)=O)O FKZSJNUXYCEZQE-UHFFFAOYSA-N 0.000 description 1
- 125000004820 3-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ZZNAYFWAXZJITH-UHFFFAOYSA-N 4-amino-3-nitrobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O ZZNAYFWAXZJITH-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
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- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
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- LUSZGTFNYDARNI-UHFFFAOYSA-N Sesamol Natural products OC1=CC=C2OCOC2=C1 LUSZGTFNYDARNI-UHFFFAOYSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- LZBCVRCTAYKYHR-UHFFFAOYSA-N acetic acid;chloroethene Chemical compound ClC=C.CC(O)=O LZBCVRCTAYKYHR-UHFFFAOYSA-N 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 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
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- 239000003795 chemical substances by application Substances 0.000 description 1
- ZJPJECQPVMSILT-UHFFFAOYSA-N chloroethene 3-(2-phenylethenyl)furan-2,5-dione Chemical compound ClC=C.O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 ZJPJECQPVMSILT-UHFFFAOYSA-N 0.000 description 1
- IEJNAGSUKYCWCR-UHFFFAOYSA-N chloroethene;1,1-dichloroethene;ethenyl acetate Chemical compound ClC=C.ClC(Cl)=C.CC(=O)OC=C IEJNAGSUKYCWCR-UHFFFAOYSA-N 0.000 description 1
- VSJDEWYENWWMAV-UHFFFAOYSA-N chloroethene;2-methylprop-2-enoic acid Chemical compound ClC=C.CC(=C)C(O)=O VSJDEWYENWWMAV-UHFFFAOYSA-N 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
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- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
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- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- RCBIPSSQLXRQJZ-UHFFFAOYSA-N methyl 2-(2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylate Chemical compound OC1=C(C=C(C=C1)OC)N1N=C2C(=N1)C=CC(=C2)C(=O)OC RCBIPSSQLXRQJZ-UHFFFAOYSA-N 0.000 description 1
- AQOJLBXKAZNFEY-UHFFFAOYSA-N methyl 2-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)benzotriazole-5-carboxylate Chemical compound C1=C(OC)C=C(C(=C1N1N=C2C=CC(C(=O)OC)=CC2=N1)O)C(C)(C)C AQOJLBXKAZNFEY-UHFFFAOYSA-N 0.000 description 1
- PGLLMZIMFVRGAQ-UHFFFAOYSA-N methyl 2-[2-hydroxy-5-methoxy-3-(2,4,4-trimethylpentan-2-yl)phenyl]benzotriazole-5-carboxylate Chemical compound OC1=C(C=C(C=C1C(C)(C)CC(C)(C)C)OC)N1N=C2C(=N1)C=CC(=C2)C(=O)OC PGLLMZIMFVRGAQ-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- LLSDTNLGZFMLPH-UHFFFAOYSA-N octyl 2-(3-tert-butyl-2-hydroxy-5-octoxyphenyl)benzotriazole-5-carboxylate Chemical compound C(C)(C)(C)C=1C(=C(C=C(C1)OCCCCCCCC)N1N=C2C(=N1)C=CC(=C2)C(=O)OCCCCCCCC)O LLSDTNLGZFMLPH-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical class NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Abstract
Description
[式中、R1は、水素原子、または炭素数1〜8のアルキル基を表し、R2は水素原子、炭素数1〜18のアルキル基、アルキル炭素数1〜7のカルボキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルオキシカルボニルアルキル基、炭素数1〜8のヒドロキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシヒドロキシアルキル基、アルキル炭素数1〜4のメタクリロイルオキシアルキル基、またはアルキル炭素数1〜4のメタクリロイルオキシヒドロキシアルキル基を表し、R3は水素原子、炭素数1〜18のアルキル基、アルキル炭素数1〜7のカルボキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルオキシカルボニルアルキル基、炭素数1〜8のヒドロキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、フェニル基、トリル基、アルキル炭素数1〜4のアクリロイルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシヒドロキシアルキル基、アルキル炭素数1〜4のメタクリロイルオキシアルキル基、またはアルキル炭素数1〜4のメタクリロイルオキシヒドロキシアルキル基である]
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: メタノール/水=95/5(リン酸3ml/L)
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC面百純度98.5%
なお、以下の実施例2〜5も本実施例と同様の測定条件でHPLC測定を行った。
<測定条件>
装置:UV−2450((株)島津製作所製)
測定波長:250〜 500nm
溶媒:クロロホルム
濃度:10ppm
なお、以下の実施例3〜6も本実施例と同様の測定条件で紫外〜可視吸収スペクトルの測定を行った。
<測定条件>
装置:JEOL JNM−AL300
共振周波数:300MHz(1H−NMR)
溶媒:クロロホルム−d
1H−NMRの内部標準物質として、テトラメチルシランを用い、ケミカルシフト値はδ値(ppm)、カップリング定数はHertzで示した。またsはsinglet、dはdoublet、mはmultipletの略とする。以下の実施例2〜6においても同様である。なお、以下の実施例2〜6も本実施例と同様の測定条件でNMR測定を行った。得られたNMRスペクトルの内容は以下のとおりである。
δ=11.44(s,1H,phenol−OH),8.73(s,1H,benzotriazole−H),8.13(d,1H,J=9.0Hz,benzotriazole−H),7.98(d,1H,J=11.1Hz,benzotriazole−H),7.82(s,1H,phenol−H),7.05(s,1H,phenol−H),6.18(s,1H,C=CH2−H),5.62(s,1H,C=CH2−H),4.65(m,2H,methacryloyl−O−CH2−H),4.56(m,2H,benzotriazole−CO−O−CH2−H),3.93(s,3H,phenol−O−CH3−H),1.98(s,3H,CH2=C−CH3−H),1.56(s,9H,tert−butyl−H)
<測定条件>
装置:UV−1850((株)島津製作所製)
測定波長:250〜 500nm
溶媒:クロロホルム
濃度:10ppm
δ=11.39(s,1H,phenol−OH),8.72(s,1H,benzotriazole−H),8.12(d,1H,J=9.0Hz,benzotriazole−H),7.96(d,1H,J=9.0Hz,benzotriazole−H),7.81(s,1H,phenol−H),7.05(s,1H,phenol−H),6.46(m,1H,CH=CH2−H),6.20(m,1H,CH2=CH−H),5.89(m,1H,CH=CH2−H),4.64(m,2H,acryloyl−O−CH2−H),4.57(m,2H,acryloyl−O−CH2−CH2−H),3.81(s,3H,phenol−O−CH3−H),1.50(s,9H,tert−butyl−H)
δ=11.40(s,1H,phenol−OH),8.69(s,1H,benzotriazole−H),8.10(m,1H,benzotriazole−H),7.96(m,1H,benzotriazole−H),7.80(s,1H,phenol−H),7.04(s,1H,phenol−H),4.04(s,3H,benzotriazole−CO−O−CH3−H),3.84(s,3H,phenol−O−CH3−H),1.50(s,9H,tert−butyl−H)
δ=11.44(s,1H,phenol−OH),8.71(s,1H,benzotriazole−H),8.11(d,1H,J=1.5Hz,benzotriazole−H),7.97(m,1H,benzotriazole−H),7.81(s,1H,phenol−H),7.05(s,1H,phenol−H),4.39(m,2H,benzotriazole−CO−O−CH2−H),3.90(s,3H,phenol−O−CH3−H),1.50(m,21H,octyl−CH2,tert−butyl−H)0.90(m,3H,octyl−CH3)
δ=11.46(s,1H,phenol−OH),8.73(s,1H,benzotriazole−H),8.13(d,1H,J=9.0Hz,benzotriazole−H),7.97(d,1H,J=9.0Hz,benzotriazole−H),7.82(s,1H,phenol−H),7.05(s,1H,phenol−H),4.32(m,2H,benzotriazole−CO−O−CH2−H),3.90(s,3H,phenol−O−CH3−H),1.50(m,18H,tert−butyl−H,2−ethylhexyl−CH2,2−ethylhexyl−CH),0.96(m,6H,2−ethylhexyl−CH3)
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:Inertsil ODS−3 4.6×150mm 5μm
カラム温度:25℃
移動相: アセトニトリル/水=9/1(リン酸3ml/L)
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC面百純度93.4%
δ=10.71(s,1H,phenol−OH),8.73(s,1H,benzotriazole−H),8.12(d,1H,J=9.6Hz,benzotriazole−H),7.98(d,1H,J=9.6Hz,benzotriazole−H),7.15(m,3H,phenol−H),6.18(s,1H,C=CH2−H),5.62(s,1H,C=CH2−H),4.65(m,2H,methacryloyl−O−CH2−H),4.57(m,2H,benzotriazole−CO−O−CH2−H),3.89(s,3H,phenol−O−CH3−H),1.98(s,3H,CH2=C−CH3−H)
従来の一般的な、紫外線を主に吸収する光吸収剤である化合物(g);3−(2H−ベンゾトリアゾール −2−イル)−4−ヒドロキシフェネチルメタクリレートを比較例として合成した。
実施例5で得られた化合物(e)を0.1g、ポリメタクリル酸メチル1.9g、メチルエチルケトン4.0g、トルエン4.0gを混合して溶解し、光吸収剤を有した樹脂組成物の溶液を得た。得られた光吸収剤を有した樹脂組成物の溶液を、バーコーターNo.20を用いてガラス板(厚み2mm)に塗布し、加熱乾燥90℃を2分、120℃を3分の順で行った後、減圧乾燥40℃を12時間実施して溶媒を除去し、膜厚4μmの光吸収剤を5%有するポリメタクリル酸メチルフィルムを得た。一方、比較例で合成した化合物(g)をメタクリル酸メチルと共重合して、5%の光吸収剤を含む共重合体とし、次いで化合物(e)と同様の方法でフィルム化して、膜厚4μmの光吸収剤を5%有するポリメタクリル酸メチルフィルムを得た。
市販の昇華転写方式コンパクトフォトプリンター(Canon SELPHY CP600)に使用されているイエロー染料、シアン染料、マゼンダ染料の転写フィルムに、上記で得られた化合物(e)、(g)の光吸収剤を5%有するポリメタクリル酸メチルフィルムを乗せて転写フィルムを保護し、ウェザーメーターで100時間疑似太陽光を照射して退色を確認した。レベル5は退色なし、レベル4はわずかに退色、レベル3はある程度退色、レベル2はほとんど退色、レベル1は完全に退色として、5段階で評価した結果を表1に示す。
装置:スーパーキセノンウェザーメーター SX−75(スガ試験機(株))
照射照度:180W/m2
照射時間:100時間
ブラックパネル温度:63℃
槽内湿度:50%
Claims (5)
- 下記の一般式(1)で表されることを特徴とするベンゾトリアゾール誘導体化合物。
[式中、R1は、水素原子、または炭素数1〜8のアルキル基を表し、R2は水素原子、炭素数1〜18のアルキル基、アルキル炭素数1〜7のカルボキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルオキシカルボニルアルキル基、炭素数1〜8のヒドロキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシヒドロキシアルキル基、アルキル炭素数1〜4のメタクリロイルオキシアルキル基、またはアルキル炭素数1〜4のメタクリロイルオキシヒドロキシアルキル基を表し、R3は水素原子、炭素数1〜18のアルキル基、アルキル炭素数1〜7のカルボキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルオキシカルボニルアルキル基、炭素数1〜8のヒドロキシアルキル基、各アルキル炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、フェニル基、トリル基、アルキル炭素数1〜4のアクリロイルオキシアルキル基、アルキル炭素数1〜4のアクリロイルオキシヒドロキシアルキル基、アルキル炭素数1〜4のメタクリロイルオキシアルキル基、またはアルキル炭素数1〜4のメタクリロイルオキシヒドロキシアルキル基である] - 上記一般式(1)におけるR1が水素原子、または炭素数1〜8のアルキル基であり、R2が炭素数1〜8のアルキル基であり、R3が水素原子、炭素数1〜8のアルキル基、アルキル炭素数1〜2のアクリロイルオキシアルキル基、またはアルキル炭素数1〜2のメタクリロイルオキシアルキル基である請求項1記載のベンゾトリアゾール誘導体化合物。
- 上記一般式(1)におけるR1が水素原子、または炭素数1〜8のアルキル基であり、R2が炭素数1〜8のアルキル基であり、R3がアルキル炭素数1〜2のアクリロイルオキシアルキル基、またはアルキル炭素数1〜2のメタクリロイルオキシアルキル基である請求項1記載のベンゾトリアゾール誘導体化合物。
- 請求項1〜3のいずれかの項に記載のベンゾトリアゾール誘導体化合物を含有する光吸収剤。
- 樹脂に、請求項1〜3のいずれかの項に記載のベンゾトリアゾール誘導体化合物を配合した光吸収性樹脂組成物。
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JP2017079707A JP6994748B2 (ja) | 2017-04-13 | 2017-04-13 | ベンゾトリアゾール誘導体化合物 |
US16/604,694 US10781187B2 (en) | 2017-04-13 | 2018-04-06 | Benzotriazole derivative compound |
KR1020197025676A KR102261129B1 (ko) | 2017-04-13 | 2018-04-06 | 벤조트리아졸 유도체 화합물 |
CN201880024612.0A CN110546141B (zh) | 2017-04-13 | 2018-04-06 | 苯并三唑衍生物化合物 |
PCT/JP2018/014816 WO2018190281A1 (ja) | 2017-04-13 | 2018-04-06 | ベンゾトリアゾール誘導体化合物 |
US16/891,231 US10919868B2 (en) | 2017-04-13 | 2020-06-03 | Benzotriazole derivative compound |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20220121794A (ko) | 2019-12-24 | 2022-09-01 | 토요잉크Sc홀딩스주식회사 | 수지 조성물, 및 성형체 |
KR20240033216A (ko) | 2021-07-14 | 2024-03-12 | 아티엔스 가부시키가이샤 | 자외선 흡수제 및 그 제조 방법, 조성물, 성형체, 도막 |
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JP6994748B2 (ja) * | 2017-04-13 | 2022-01-14 | シプロ化成株式会社 | ベンゾトリアゾール誘導体化合物 |
CN115776992A (zh) | 2020-08-21 | 2023-03-10 | 富士胶片株式会社 | 聚合性组合物、聚合物、紫外线遮蔽材料、层叠体、化合物、紫外线吸收剂及化合物的制造方法 |
JPWO2022071497A1 (ja) * | 2020-09-30 | 2022-04-07 | ||
KR20230007414A (ko) * | 2020-09-30 | 2023-01-12 | 호야 렌즈 타일랜드 리미티드 | 안경 렌즈 |
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KR102261129B1 (ko) | 2021-06-03 |
CN110546141B (zh) | 2023-03-28 |
WO2018190281A1 (ja) | 2018-10-18 |
US20200157059A1 (en) | 2020-05-21 |
US10919868B2 (en) | 2021-02-16 |
CN110546141A (zh) | 2019-12-06 |
US20200290981A1 (en) | 2020-09-17 |
JP6994748B2 (ja) | 2022-01-14 |
KR20190113896A (ko) | 2019-10-08 |
US10781187B2 (en) | 2020-09-22 |
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