JP2018135282A - ベンゾトリアゾール誘導体化合物及びそれらの重合体 - Google Patents
ベンゾトリアゾール誘導体化合物及びそれらの重合体 Download PDFInfo
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- JP2018135282A JP2018135282A JP2017029521A JP2017029521A JP2018135282A JP 2018135282 A JP2018135282 A JP 2018135282A JP 2017029521 A JP2017029521 A JP 2017029521A JP 2017029521 A JP2017029521 A JP 2017029521A JP 2018135282 A JP2018135282 A JP 2018135282A
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- carbon atoms
- alkyl
- wavelength conversion
- alkyl carbon
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- -1 Benzotriazol derivative compound Chemical class 0.000 title claims abstract description 122
- 229920000642 polymer Polymers 0.000 title description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 86
- 239000000463 material Substances 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229920001577 copolymer Polymers 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000005425 toluyl group Chemical group 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000005259 measurement Methods 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003505 polymerization initiator Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 230000008033 biological extinction Effects 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- IXSGSKLRBBVFPR-UHFFFAOYSA-N C1=CC(=CC=C1N2N=C3C=CC(=CC3=N2)C(=O)O)O Chemical compound C1=CC(=CC=C1N2N=C3C=CC(=CC3=N2)C(=O)O)O IXSGSKLRBBVFPR-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- MMKSJYOTPVLBDU-UHFFFAOYSA-N CCCCCCCCOC1=CC=C(C=C1)N2N=C3C=CC(=CC3=N2)C(=O)OCCOC(=O)C(=C)C Chemical compound CCCCCCCCOC1=CC=C(C=C1)N2N=C3C=CC(=CC3=N2)C(=O)OCCOC(=O)C(=C)C MMKSJYOTPVLBDU-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- ZKECVHXIVHRIIA-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-1-yl)prop-2-enamide Chemical compound CC1(C)CCCC(C)(C)N1NC(=O)C=C ZKECVHXIVHRIIA-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 238000012662 bulk polymerization Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 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 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000695 excitation spectrum Methods 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000003999 initiator Substances 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007870 radical polymerization initiator Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 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 3
- 229920001897 terpolymer Polymers 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SQASHPHWVSAHDM-UHFFFAOYSA-N 4h-benzotriazole-5-carboxylic acid Chemical compound C1C(C(=O)O)=CC=C2N=NN=C21 SQASHPHWVSAHDM-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- CJKWDYKIIZGPFQ-UHFFFAOYSA-N COC(=O)C1=CC2=NN(N=C2C=C1)C3=CC=C(C=C3)O Chemical compound COC(=O)C1=CC2=NN(N=C2C=C1)C3=CC=C(C=C3)O CJKWDYKIIZGPFQ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 244000028419 Styrax benzoin Species 0.000 description 2
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- HGXVVEAFYUQTPU-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC(=C1)C(=O)O)N=NC1=CC=C(C=C1)O Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)C(=O)O)N=NC1=CC=C(C=C1)O HGXVVEAFYUQTPU-UHFFFAOYSA-N 0.000 description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
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- 239000007850 fluorescent dye Substances 0.000 description 2
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- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 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 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- OZTYRAWXWCSOAF-DIYDOPDJSA-N tetramethylsilane;trichloro(deuterio)methane Chemical compound [2H]C(Cl)(Cl)Cl.C[Si](C)(C)C OZTYRAWXWCSOAF-DIYDOPDJSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/52—PV systems with concentrators
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Abstract
Description
[式中R1は、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、各アルキルの炭素数の合計が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、各アルキルの炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、ホルミル基、アルキル炭素数1〜7のアルキルカルボニル基、ベンゾイル基、トルオイル基、アクリロイル基、メタクリロイル基、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、R2は、水素原子、炭素数1〜18のアルキル基、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り、
かつ、R1がアクリロイル基、メタクリロイル基、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もしくはアルキル炭素数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か、および/またはR2がアルキル炭素数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もしくはアルキル炭素数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]
かつ、R1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もしくはアルキル炭素数1〜2メタクリロイルオキシアルキル基であるか、および/またはR2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もしくはアルキル炭素数1〜2のメタクリロイルオキシアルキル基である。
かつ、R1がアクリロイル基、メタクリロイル基、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もしくはアルキル炭素数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か、および/またはR2がアルキル炭素数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もしくはアルキル炭素数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。
かつ、R1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もしくはアルキル炭素数1〜2メタクリロイルオキシアルキル基であるか、および/またはR2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もしくはアルキル炭素数1〜2のメタクリロイルオキシアルキル基である化合物である。
2−メタクリロイルオキシエチル 2−(4−メトキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、2−メタクリロイルオキシエチル 2−(4−アセトキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、2−メタクリロイルオキシエチル 2−(4−メタクリロイルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、2−メタクリロイルオキシエチル 2−[4−(2−メタクリロイルオキシエトキシ)フェニル]−2H−ベンゾトリアゾール−5−カルボキシレート、4−メタクリロイルオキシブチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、2−アクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、オクチル 2−[4−(2−アクリロイルオキシエトキシ)フェニル]−2H−ベンゾトリアゾール−5−カルボキシレート、メチル 2−[4−(2−メタクリロイルオキシエトキシ)フェニル]−2H−ベンゾトリアゾール−5−カルボキシレート、オクチル 2−[4−(2−メタクリロイルオキシエトキシ)フェニル]−2H−ベンゾトリアゾール−5−カルボキシレート。
[中間体;5−カルボキシ −2−(4−ヒドロキシフェニル)−2H−ベンゾトリアゾール]の合成
<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=99/1
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC面百純度99.0%
<測定条件>
装置:JEOL−ECX400
共振周波数:400MHz(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、tはtriplet、mはmultipletの略とする。以下の実施例3においても同様である。得られたNMRスペクトルの内容は以下のとおりである。
σ=8.71(s,1H,benzotriazole−H),8.28(m,2H,benzotriazole−H),8.05(d,1H,J=8.0Hz,benzene−H),7.95(d,1H,J=8.0Hz,benzene−H),7.06(m,2H,benzene−H),6.17(s,1H,C=CH2−H),5.61(s,1H,C=CH2−H),4.64(t,2H,benzotriazole−CO−O−CH2−H),4.54(t,2H,methacryloyl−O−CH2−H),4.05(t,2H,benzene−O−CH2−H),1.97(s,3H,CH2−C−CH3−H),1.83(m,2H,O−CH2−CH2−H),1.48(m,2H,O−CH2−CH2−CH2−H),1.33(m,8H,(CH2)4−H),0.89(t,3H,CH3−H)
<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
流速:1.0ml/min
検出:UV250nm
<測定結果>
HPLC面百純度99.8%
<測定条件>
装置:JEOL−ECX400
共振周波数:400MHz(1H−NMR)
溶媒:DMSO−d
得られたNMRスペクトルの内容は以下のとおりである。
σ=8.65(s,1H,benzotriazole−H),8.27(m,2H,benzotriazole−H),8.14(d,1H,J=9.2Hz,benzene−H),8.01(d,1H,J=1.2Hz,benzene−H),7.25(m,2H,benzene−H),6.06(s,1H,C=CH2−H),5.71(s,1H,C=CH2−H),4.49(t,2H,methacryloyl−O−CH2−H),4.39(t,2H,benzene−O−CH2−H),3.93(s,3H,benzotriazole−CO−O−CH3−H),1.89(s,3H,CH2−C−CH3−H)
[重合体(a);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを有する重合体の合成]
100ml4つ口フラスコにジムロート冷却器、水銀温度計、窒素ガス吹き込み管、撹拌装置を取り付け、重合性化合物としての化合物(a);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを0.125g、メチルメタクリレート(以下、「MMA」と記す。)を4.875g、および、溶媒としてのトルエン10g、メチルエチルケトン(以下、「MEK」と記す。)を10g、および、重合開始剤としての1,1’−アゾビス(シクロヘシサン−1−カルボニトリル)(以下、「ACN」と記す。)を0.1g仕込み、撹拌しながら窒素ガス流量5ml/minで1時間フラスコ内を窒素置換後に昇温を行い、反応液温度88〜91℃で10時間還流状態にて重合反応を行い、重合体(a)の溶液25.1gを得た。
[重合体(b);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを有する重合体の合成
100ml4つ口フラスコにジムロート冷却器、水銀温度計、窒素ガス吹き込み管、撹拌装置を取り付け、重合性化合物としての化合物(a);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを0.125g、MMAを1.875g、シクロヘシキルメタクリレート(以下、「CHMA」と記す。)2.0g、スチレン1.0g、および、溶媒としてのトルエン10g、MEKを10g、および、重合開始剤としてのACNを0.05g仕込み、撹拌しながら窒素ガス流量5ml/minで1時間フラスコ内を窒素置換後に昇温を行い、反応液温度88〜91℃で10時間還流状態にて重合反応を行い、重合体(b)の溶液25.05gを得た。
[重合体(c);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを有する重合体の合成
100ml4つ口フラスコにジムロート冷却器、水銀温度計、窒素ガス吹き込み管、撹拌装置を取り付け、重合性化合物としての化合物(a);2−メタクリロイルオキシエチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを0.125g、MMAを2.125g、CHMAを2.25g、2−ヒドロキシエチルメタクリレート(以下、「HEMA」と記す。)0.5g、および、溶媒としてのトルエン10g、MEKを10g、および、重合開始剤としてのACNを0.1g仕込み、撹拌しながら窒素ガス流量5ml/minで1時間フラスコ内を窒素置換後に昇温を行い、反応液温度88〜91℃で10時間還流状態にて重合反応を行い、重合体(c)の溶液25.1gを得た。
上記の実施例4〜6により得られた重合体(a)〜(c)の合成処方仕込み量と分子量を表1に示す。共重合体の分子量はGPCシステムHLC−8320GPC EcoSEC(東ソー株式会社)を用い、溶離液をテトラヒドロフラン、分離カラムをTSKgelGMHXL−L(東ソー株式会社)として、ポリスチレン検量線を用いたポリスチレン換算の重量平均分子量(Mw)、数平均分子量(Mn)、多分散度(Mw/Mn)を測定した。
従来に提案されているベンゾトリアゾール誘導体化合物であり、一般式(1)と異なる構造である、化合物(c);2−メタクリロイルオキシエチル 2−(3−メトキシ−4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレート、化合物(d);2−メタクリロイルオキシエチル 2−(3,5−ジメトキシ−4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートを比較例として合成した。また、従来の一般的な青色発光材料であり、ナフタルイミド誘導体である化合物(e);N−[2−(4−tert−ブチルフェニル)−1,3−ジオキソ−2,3−ジヒドロ−1H−ベンゾ[de]イソキノリン−6−イル]アセトアミドを比較例として合成した。
上記の実施例及び比較例で得られた化合物(a)〜(e)のクロロホルム中での吸収及び発光特性を表2に示す。
上記の比較例で得られた化合物(e)を0.05g、ポリメタクリル酸メチル1.95g、メチルエチルケトン4.00g、トルエン4.00gを混合し、波長変換材料を有した樹脂組成物の溶液を得た。得られた波長変換材料を有した樹脂組成物の溶液、及び実施例4〜6で得られた重合体(a)、(b)、(c)の溶液を、バーコーターNo.20を用いてガラス板(セントラル社製「フロートガラス板」、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24時間実施して溶媒を除去、波長変換材料が2.5%添加された膜厚4μmのフィルムを得た。
上記で得られた化合物(e)、重合体(a)、(b)、(c)のフィルムでの吸収及び発光特性を表3に示す。
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
セル:1cm石英
装置: U−3900H((株)日立ハイテクサイエンス製)
測定波長:310〜510nm
装置:FP−8500(日本分光(株)製)
測定波長:200〜850nm
溶媒:クロロホルム
濃度:10ppm
セル:1cm石英
装置:FP−8500(日本分光(株)製)
測定波長:200〜 850nm
Claims (8)
- 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、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、各アルキルの炭素数の合計が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、各アルキルの炭素数の合計が2〜15のアルキルカルボニルオキシアルキル基、ホルミル基、アルキル炭素数1〜7のアルキルカルボニル基、ベンゾイル基、トルオイル基、アクリロイル基、メタクリロイル基、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、R2は、水素原子、炭素数1〜18のアルキル基、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り、
かつ、R1がアクリロイル基、メタクリロイル基、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もしくはアルキル炭素数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か、および/またはR2がアルキル炭素数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もしくはアルキル炭素数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り、R2が炭素数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り、
かつ、R1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もしくはアルキル炭素数1〜2メタクリロイルオキシアルキル基であるか、および/またはR2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、もしくはアルキル炭素数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2に記載のベンゾトリアゾール誘導体化合物を重合して得られる単重合体。
- 請求項2に記載のベンゾトリアゾール誘導体化合物とラジカル重合性不飽和二重結合を有する化合物とを重合して得られる共重合体。
- 前記ラジカル重合性不飽和二重結合を有する化合物が、(メタ)アクリロイル基を有する化合物である請求項4に記載の共重合体。
- 請求項1〜2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または請求項3〜5のいずれかの項に記載の(共)重合体を含む波長変換材料。
- 請求項6に記載の波長変換材料を用いた農業用波長変換フィルム。
- 請求項6に記載の波長変換材料を用いた太陽電池用波長変換フィルム。
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JP2016169181A (ja) * | 2015-03-12 | 2016-09-23 | シプロ化成株式会社 | ベンゾトリアゾール誘導体化合物及びそれらの重合体 |
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