WO2014069198A1 - 塗料及び近赤外線吸収フィルター - Google Patents
塗料及び近赤外線吸収フィルター Download PDFInfo
- Publication number
- WO2014069198A1 WO2014069198A1 PCT/JP2013/077446 JP2013077446W WO2014069198A1 WO 2014069198 A1 WO2014069198 A1 WO 2014069198A1 JP 2013077446 W JP2013077446 W JP 2013077446W WO 2014069198 A1 WO2014069198 A1 WO 2014069198A1
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- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- paint
- solvent
- acid
- Prior art date
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- 239000003973 paint Substances 0.000 title claims abstract description 30
- 238000010521 absorption reaction Methods 0.000 title abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 abstract description 5
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- -1 cyanine compound Chemical class 0.000 description 64
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 51
- 239000000975 dye Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Chemical class 0.000 description 5
- 229940085991 phosphate ion Drugs 0.000 description 5
- 150000007519 polyprotic acids Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000008366 benzophenones Chemical class 0.000 description 4
- 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 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002484 inorganic compounds Chemical class 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229940049920 malate Drugs 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-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
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- SJNALLRHIVGIBI-UHFFFAOYSA-N allyl cyanide Chemical compound C=CCC#N SJNALLRHIVGIBI-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000004566 building material Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000009125 cardiac resynchronization therapy Methods 0.000 description 2
- 238000001444 catalytic combustion detection Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002734 clay mineral Substances 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 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 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- 150000002513 isocyanates Chemical class 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 1
- UUIPAJHTKDSSOK-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)(O)=O UUIPAJHTKDSSOK-UHFFFAOYSA-N 0.000 description 1
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 1
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- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/32—Radiation-absorbing paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B53/00—Quinone imides
- C09B53/02—Indamines; Indophenols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- 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
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
Definitions
- the present invention relates to an infrared absorbing dye, a resin and a paint containing diacetone alcohol as a solvent, and a near infrared absorbing filter formed using the paint.
- Near-infrared absorption filters have high transmittance in the visible light region and can block infrared rays efficiently.
- Display panels such as plasma display panels, CRTs, fluorescent display tubes, field emission displays; cameras, video cameras, etc.
- Patent Document 1 discloses a positive photosensitive resin composition containing diacetone alcohol as a solvent
- Patent Document 2 discloses a colorant-containing curable composition containing a colorant and a solvent.
- Diacetone alcohol is exemplified as the solvent
- Patent Document 3 discloses a positive photosensitive resin composition containing diacetone alcohol as a solvent
- Patent Document 4 discloses an ink containing an acid dye and an alcohol-based organic solvent
- Patent Document 5 discloses a near-infrared absorption filter obtained using a diimonium compound.
- Patent Documents 1 to 5 do not describe or suggest that the use of diacetone alcohol as a solvent improves the light resistance of a film obtained by applying a paint to a substrate.
- an object of the present invention is to provide a near-infrared absorption filter having high light resistance.
- the present inventor used a paint containing an infrared absorbing dye (A), a resin (B) and a solvent (C), and having diacetone alcohol as an essential component as a solvent (C) component.
- the near-infrared absorption filter formed was found to have high light resistance and reached the present invention.
- the present invention provides a paint containing an infrared-absorbing dye (A), a resin (B) and a solvent (C), and having diacetone alcohol as an essential component as a solvent (C) component.
- the present invention also provides a near-infrared absorption filter formed using the above-mentioned paint.
- the near-infrared absorption filter of the present invention is excellent in terms of high light resistance.
- the infrared absorbing dye (A) those having characteristic absorption in the infrared region and conventionally used as a (near) infrared absorbing dye can be used.
- a cyanine compound examples include squarylium compounds, porphyrin compounds, metal dithiol complexes, chromium, cobalt metal complex compounds, anthraquinones, phthalocyanine compounds, naphthalocyanine compounds, diimonium compounds, and inorganic oxide particles. It is preferable because of its high transparency in the visible light region.
- R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently a hydrogen atom or a C 1-10 carbon atom which may have a substituent.
- An methylene group in the alkyl group may be substituted with —O— or —CH ⁇ CH—, t represents a number of 1 to 4, and
- An q ⁇ represents a q valence.
- Q represents 1 or 2
- p represents a coefficient for keeping the charge neutral.
- substituents represented by R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 and R 22 examples of the alkyl group having 1 to 10 carbon atoms that may have are methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, cyclohexyl Methyl, cyclohexylethyl, heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, trifluoromethyl, trichloromethyl, tribromo
- the amino group which may have a substituent represented by R 19 , R 20 , R 21 and R 22 includes amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecyl.
- Examples of the q-valent anion represented by pAn q- in the general formula (I) include methanesulfonate anion, dodecylsulfonate anion, benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion, naphthalenesulfone.
- chloride ions bromide ions, iodide ions, fluoride ions, chlorate ions, thiocyanate ions, perchlorate ions, hexafluorophosphate ions, hexafluoroantimonate ions, tetrafluoroborate ions, Octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphonate ion, tetrakis (penta Fluorophenyl) borate ion, excitation Quencher anions that have the function of deexciting (quenching) active molecules in the state, ferrocene, luteocene, etc. having an anionic group such as a carboxy
- dye (A) can be used individually or in combination of multiple types.
- the content of the compound represented by the general formula (I) is preferably 50 to 100% by mass, more preferably 70 to 100% by mass.
- content of the compound represented by the said general formula (I) is smaller than 50 mass%, the solubility to a solvent may fall or heat resistance may fall.
- the infrared absorbing dye (A) preferably has a maximum absorption wavelength ( ⁇ max) of the coating film of 700 nm or more, more preferably 780 to 850 nm. If the maximum absorption wavelength ( ⁇ max) of the coating film is less than 700 nm, it is not preferable because it does not absorb light of the target wavelength.
- the content of the infrared absorbing dye (A) is preferably 0.01 to 50% by mass, more preferably 0.1 to 10% by mass in the paint of the present invention. If the content of the infrared absorbing dye (A) is less than 0.01% by mass, the near-infrared absorbing filter formed using the paint of the present invention may not absorb the target wavelength, and if it is greater than 50% by mass. In some cases, the infrared absorbing dye (A) is precipitated in the paint.
- the resin (B) is not particularly limited as long as it can uniformly disperse the infrared absorbing dye (A), but polyester, polyacryl, polyamide, polyurethane, polyolefin, Resins such as polycarbonate resins, and resins obtained by crosslinking these resins with organic peroxides, crosslinking agents, photocrosslinking initiators, and the like can be suitably used.
- the glass transition temperature of the resin and the glass transition temperature of the cured film (near infrared absorption filter) obtained by applying a coating containing the resin to the substrate are preferably equal to or higher than the guaranteed use temperature of the equipment to be used. .
- a polyacrylic resin is preferable from the viewpoint of compatibility with the infrared absorbing dye (A), and further a polymer obtained by polymerizing a polymerizable compound having an ethylenically unsaturated bond, alone or in plural. preferable.
- the polymerizable compound having an ethylenically unsaturated bond is not particularly limited and conventionally known compounds can be used. Examples thereof include ethylene, propylene, butylene, isobutylene, vinyl chloride, vinylidene chloride, and vinylidene fluoride.
- Unsaturated aliphatic hydrocarbons such as tetrafluoroethylene; (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinylacetic acid, allyl Acetic acid, cinnamic acid, sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meth) Mono (meta) of polymer having carboxy group and hydroxyl group at both ends such as acrylate Acrylate, hydroxyethyl (meth) acrylate / malate, hydroxypropyl (meth) acrylate / malate, dicyclopentadiene / malate or polyfunctional (meth)
- A1-No. A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, (t-butyl) (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxy
- Polyacrylic resins can be obtained by polymerizing these polymerizable compounds alone or in combination of two or more.
- the organic peroxide used to obtain the resin is preferably one that easily generates a peroxy radical in the presence of heat or a redox system.
- the radical generated from the peroxide generates a radical in the polymer main chain by the hydrogen abstraction reaction of the polymer main chain, and takes a cross-linking form in which the entire polymer main chain is cross-linked. Incorporated into the structure and uniformly crosslinked.
- crosslinking agent used to obtain the resin examples include polyfunctional epoxy compounds, polyfunctional isocyanates, diacid anhydrides, acetophenones, benzophenones, anthraquinones, triazines, aziridines, melamine compounds, metal salts, metal chelate compounds, etc .; polyfunctional acrylates UV crosslinking agents such as olefinically unsaturated compounds and copolymerizable benzophenones; hydroxy ketones, benzyl dimethyl ketals, amino ketones, acylphosphine oxides, benzophenones, trichloromethyl group-containing triazine derivatives, polyfunctional benzophenones, acrylics Oligomer obtained by polymerizing benzophenone, primary hydroxyl group of 1- [4- (2-hydroxyethoxy) phenyl] -2-hydroxy-2-methyl-1-propan-1-one and 2-isocyanatoethyl Oligomers obtained by polymerizing the reaction product of Relate, 2-hydroxy-2-
- Examples of the photocrosslinking initiator used to obtain the resin include 2-methyl-1 [4- (methylthio) phenyl] -2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1- ( ⁇ -amino ketones such as 4-morpholinophenyl) -butanone-1, ⁇ -hydroxy such as 1-hydroxy-cyclohexyl-phenyl-ketone and 2-hydroxy-2-methyl-1-phenyl-propion-1-one Examples thereof include ketone series and benzyldimethyl ketal series such as 2,2-dimethoxy-1,2-diphenylethane-1-one.
- the content of the resin (B) is preferably 30 to 99% by mass, particularly 60 to 95% by mass in the solid content of the coating material of the present invention.
- the content of the resin (B) is less than 30% by mass, the adhesion of the near infrared absorption filter after application to the substrate may be reduced.
- the content is more than 99% by mass, the near infrared absorption filter The strength may decrease.
- diacetone alcohol is an essential component, and in addition, each of the above components (the infrared absorbing dye (A) of the present invention, etc.) is usually dissolved or dispersed as necessary. It can be used by mixing with a solvent.
- solvents include ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane.
- Ether solvents such as 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol Ester solvents such as ethylene glycol monomethyl ether, cellosolve solvents such as ethylene glycol monoethyl ether; methanol, ethanol, iso- or n-propanol, iso- or Alcohol solvents such as n-butanol and amyl alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-acetate (PGMEA), dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate Ether ether solvents such as eth
- Terpene hydrocarbon oils mineral spirits, paraffinic solvents such as Swazol # 310 (Cosmo Matsuyama Oil), Solvesso # 100 (Exxon Chemical); carbon tetrachloride, chloroform, Halogenated aliphatic hydrocarbon solvents such as chloroethylene, methylene chloride, 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents, aniline, triethylamine, pyridine, acetic acid, acetonitrile, Examples thereof include carbon sulfide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, water and the like, and these solvents can be used as one or a mixture of two or more.
- ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, dimethylacetamide, cyclohexanone, etc., are used as infrared absorbing dye (A) or resin (B) in the paint of the present invention. It is preferable because of good compatibility.
- diacetone alcohol is 30 to 100% by mass, particularly 50 to 95% by mass, based on the total amount of the solvent (C), because the liquid stability is good.
- the amount of the solvent (C) used is such that the concentration of the composition other than the solvent (C) is preferably 5 to 30% by mass, and if it is less than 5% by mass, the film thickness is increased. This is not preferable because it is difficult to absorb the light of the desired wavelength, and when it exceeds 30% by mass, the storage stability of the composition due to the precipitation of the composition is reduced, and the handling is reduced because the viscosity is improved. Therefore, it is not preferable.
- the coating material of the present invention can further contain an inorganic compound.
- the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable.
- the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the acrylic resin. Can use 1 type (s) or 2 or more types.
- inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
- the paint of the present invention contains, if necessary, a dye other than the infrared absorbing dye of the present invention; a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; a thermal polymerization initiator.
- a dye other than the infrared absorbing dye of the present invention e.g., a thermal polymerization inhibitor such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- a thermal polymerization initiator e.g., p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- a thermal polymerization initiator e.g., p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
- the content of optional components other than the infrared-absorbing dye (A) and the resin (B) (excluding the solvent (C)) is appropriately selected according to the purpose of use and is not particularly limited. Preferably, it is 50 parts by mass or less in total with respect to 100 parts by mass of the resin (B).
- the near-infrared absorption filter of the present invention can be obtained by applying the paint of the present invention on a substrate.
- substrate is not specifically limited, As the preferable example, a glass plate, a polyethylene terephthalate board, a polycarbonate board, a polyimide board, a polyamide board, a polymethyl methacrylate board, a polystyrene board, a polyvinyl chloride board, a polyolefin board, a cycloolefin Polymer plate, polytetrafluoroethylene plate, triacetylcellulose plate, norbornene plate, polyvinyl alcohol plate, cellulose acetate plate, polyarylate plate, polysulfone plate, polyethersulfone plate, silicon wafer, reflector, calcite plate, quartz plate, glass A board, paper, wood, a metal plate, etc. are mentioned.
- the substrate may be subjected to surface treatment by a conventionally known method such as corona discharge treatment, flame treatment, plasma treatment, glow discharge treatment, roughening treatment, chemical treatment, or coating such as an anchor coating agent or a primer.
- known methods can be used, for example, curtain coating method, extrusion coating method, roll coating method, spin coating method, dip coating method, bar coating method, spray coating method, slide coating method. Method, blade coating method, gravure coating method, printing coating method and the like can be used.
- the near-infrared absorption filter of the present invention has a transmittance in the (near) infrared region of 800 to 1100 nm of 10% or less, preferably 8% or less.
- the near-infrared absorption filter of the present invention is a display panel such as a plasma display panel, a CRT, a fluorescent display tube, and a field emission display; a photodiode used in a light receiving element or an imaging element of an optical device such as a camera or a video camera; CCD, C-MOS; heat-shielding filters for optical lenses, glass for automobiles, glass for building materials, solar cell modules, etc .; light receiving elements and imaging elements for optical devices such as video cameras; infrared absorbing ink and toner applications; Infrared photosensitive safe light filters, photosensitive materials using infrared semiconductor laser light as a light source, optical disc recording materials, etc .; anti-counterfeiting applications such as cash cards and ID cards; infrared rays contained in sunlight Dimmable materials for absorption; Agricultural materials such as plant growth control; Can be used to protect medical materials and various applications, there is no particular limitation on the application.
- a display panel such as a plasma display panel
- Example 1 Paint No. 1 Preparation of Compound No. 1 as component (A) 0.05 g of bis (trifluoromethanesulfonyl) imide salt 1 and 2.75 g of diacetone alcohol as component (C) were added and dissolved by stirring. Thereafter, 5 g of SPC-2000 (manufactured by Showa Denko KK) was mixed as component (B) and stirred until the insoluble matter disappeared. 1 was obtained.
- Examples 2-6 and Comparative Examples 1-2 2 to No. 6 and comparative paint no. 1-No. Adjustment of No. 2
- each component was mixed according to the formulation shown in [Table 1]. 2 to No. 6 and comparative paint no. 1-No. 2 was obtained.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Optical Filters (AREA)
- Paints Or Removers (AREA)
Abstract
Description
R19、R20、R21及びR22で表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、
R19、R20、R21及びR22で表される置換基を有してもよいアミノ基としては、アミノ、エチルアミノ、ジメチルアミノ、ジエチルアミノ、ブチルアミノ、シクロペンチルアミノ、2-エチルヘキシルアミノ、ドデシルアミノ、アニリノ、クロロフェニルアミノ、トルイジノ、アニシジノ、N-メチル-アニリノ、ジフェニルアミノ,ナフチルアミノ、2-ピリジルアミノ、メトキシカルボニルアミノ、フェノキシカルボニルアミノ、アセチルアミノ、ベンゾイルアミノ、ホルミルアミノ、ピバロイルアミノ、ラウロイルアミノ、カルバモイルアミノ、N,N-ジメチルアミノカルボニルアミノ、N,N-ジエチルアミノカルボニルアミノ、モルホリノカルボニルアミノ、メトキシカルボニルアミノ、エトキシカルボニルアミノ、t-ブトキシカルボニルアミノ、n-オクタデシルオキシカルボニルアミノ、N-メチル-メトキシカルボニルアミノ、フェノキシカルボニルアミノ、スルファモイルアミノ、N,N-ジメチルアミノスルホニルアミノ、メチルスルホニルアミノ、ブチルスルホニルアミノ、フェニルスルホニルアミノ等が挙げられる。
上記赤外線吸収色素(A)において、上記一般式(I)で表わされる化合物の含有量は、好ましくは50~100質量%、より好ましくは70~100質量%である。上記一般式(I)で表わされる化合物の含有量が50質量%より小さいと、溶媒への溶解性が低下したり、耐熱性が低下したりする場合がある。
本発明の近赤外線吸収フィルターは、本発明の塗料を基板上に塗布することにより得られる。
該基板は、コロナ放電処理、火炎処理、プラズマ処理、グロー放電処理、粗面化処理、薬品処理等の従来公知の方法による表面処理や、アンカーコート剤やプライマー等のコーティングを施しても良い。
(A)成分として化合物No.1のビス(トリフルオロメタンスルホニル)イミド塩を0.05gと、(C)成分としてジアセトンアルコール2.75gを加え、撹拌して溶解した。その後、(B)成分としてSPC-2000(昭和電工社製)5gを混合し、不溶物が無くなるまで撹拌し、塗料No.1を得た。
実施例1と同様の手順で、[表1]に示す配合で各成分を混合し、塗料No.2~No.6及び比較塗料No.1~No.2を得た。
東レ社製PETフィルムであるルミラーU98の上に実施例1~6で得られた塗料No.1~No.6及び比較例1~2で得られた比較塗料No.1~No.2の2.5mLを滴下し、#14バーコーターを用いて塗布した。その後、100℃で15分間乾燥して、近赤外線吸収フィルターNo.1~No.6及び比較近赤外線吸収フィルターNo.1~No.2を製造した。
実施例1~6で得られた近赤外線吸収フィルターNo.1~No.6及び比較例1~2で得られた比較近赤外線吸収フィルターNo.1~No.2について、スガ試験機製キセノン耐光性試験機テーブルサンXT-1500Lにて25時間耐光性試験を実施し、1000nmにおける吸光度残存率を評価した。吸光度残存率は試験前の吸光度に対する試験後の吸光度の比率として算出した。評価結果を[表2]に示す。
Claims (4)
- 赤外線吸収色素(A)、樹脂(B)及び溶媒(C)を含有し、溶媒(C)成分としてジアセトンアルコールを必須成分とする塗料。
- 上記赤外線吸収色素(A)がジイモニウム化合物であることを特徴とする請求項1記載の塗料。
- 上記ジイモニウム化合物が下記一般式(I)で表されるジイモニウム化合物であることを特徴とする請求項2記載の塗料。
- 請求項1~3のいずれか1項に記載の塗料を用いて形成される近赤外線吸収フィルター。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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KR1020147035974A KR20150080451A (ko) | 2012-11-01 | 2013-10-09 | 도료 및 근적외선 흡수 필터 |
CN201380033258.5A CN104379688B (zh) | 2012-11-01 | 2013-10-09 | 涂料及近红外线吸收滤波器 |
JP2014544403A JP6301841B2 (ja) | 2012-11-01 | 2013-10-09 | 塗料及び近赤外線吸収フィルター |
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JP (1) | JP6301841B2 (ja) |
KR (1) | KR20150080451A (ja) |
CN (1) | CN104379688B (ja) |
TW (1) | TWI596173B (ja) |
WO (1) | WO2014069198A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015198782A1 (ja) * | 2014-06-25 | 2015-12-30 | ソニー株式会社 | 赤外光カットフィルタ、固体撮像素子及び撮像装置 |
JP2018054760A (ja) * | 2016-09-27 | 2018-04-05 | 株式会社日本触媒 | 光選択吸収樹脂積層体 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105207576A (zh) * | 2015-10-28 | 2015-12-30 | 蒋安为 | 一种红外线发电器 |
JP6833728B2 (ja) | 2016-01-29 | 2021-02-24 | 富士フイルム株式会社 | 組成物、膜、近赤外線カットフィルタ、積層体、パターン形成方法、固体撮像素子、画像表示装置、赤外線センサおよびカラーフィルタ |
US11300719B2 (en) * | 2016-11-14 | 2022-04-12 | Nippon Sheet Glass Company, Limited | Light-absorbing composition and optical filter |
KR102009974B1 (ko) | 2018-10-31 | 2019-08-12 | (주)케미그라스 | 근적외선 차단렌즈 |
JP7419097B2 (ja) * | 2020-02-18 | 2024-01-22 | 東京応化工業株式会社 | 硬化性組成物、硬化物、近赤外線吸収フィルタ、硬化物の製造方法、近赤外線吸収フィルタの製造方法、硬化性組成物の低温保管方法、硬化性組成物の輸送方法、及び硬化性組成物の提供方法 |
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JPH05178808A (ja) * | 1992-04-15 | 1993-07-20 | Canon Inc | ジイモニウム塩化合物 |
JPH06220420A (ja) * | 1993-01-21 | 1994-08-09 | Canon Inc | 赤外吸収化合物及びそれを用いた光記録媒体 |
JPH07267683A (ja) * | 1994-03-30 | 1995-10-17 | Central Glass Co Ltd | 紫外線赤外線吸収透明体 |
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JPH06256754A (ja) * | 1993-03-04 | 1994-09-13 | Canon Inc | 赤外吸収化合物及びそれを用いた光記録媒体 |
JPH07133437A (ja) * | 1993-11-09 | 1995-05-23 | Canon Inc | 赤外吸収化合物及びそれを用いた光記録媒体 |
US7524619B2 (en) * | 2002-11-22 | 2009-04-28 | Japan Carlit Co., Ltd. | Coloring matter absorbing near-infrared ray and filter for cutting off near-infrared ray |
US7332257B2 (en) * | 2003-07-11 | 2008-02-19 | Asahi Glass Company, Limited | Composition for optical film, and optical film |
JP5004506B2 (ja) * | 2005-06-24 | 2012-08-22 | 株式会社Adeka | 光学フィルター |
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2013
- 2013-10-09 JP JP2014544403A patent/JP6301841B2/ja active Active
- 2013-10-09 KR KR1020147035974A patent/KR20150080451A/ko not_active Application Discontinuation
- 2013-10-09 CN CN201380033258.5A patent/CN104379688B/zh not_active Expired - Fee Related
- 2013-10-09 WO PCT/JP2013/077446 patent/WO2014069198A1/ja active Application Filing
- 2013-10-16 TW TW102137340A patent/TWI596173B/zh active
Patent Citations (3)
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JPH05178808A (ja) * | 1992-04-15 | 1993-07-20 | Canon Inc | ジイモニウム塩化合物 |
JPH06220420A (ja) * | 1993-01-21 | 1994-08-09 | Canon Inc | 赤外吸収化合物及びそれを用いた光記録媒体 |
JPH07267683A (ja) * | 1994-03-30 | 1995-10-17 | Central Glass Co Ltd | 紫外線赤外線吸収透明体 |
Cited By (2)
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WO2015198782A1 (ja) * | 2014-06-25 | 2015-12-30 | ソニー株式会社 | 赤外光カットフィルタ、固体撮像素子及び撮像装置 |
JP2018054760A (ja) * | 2016-09-27 | 2018-04-05 | 株式会社日本触媒 | 光選択吸収樹脂積層体 |
Also Published As
Publication number | Publication date |
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CN104379688B (zh) | 2018-05-25 |
KR20150080451A (ko) | 2015-07-09 |
CN104379688A (zh) | 2015-02-25 |
TW201430080A (zh) | 2014-08-01 |
TWI596173B (zh) | 2017-08-21 |
JPWO2014069198A1 (ja) | 2016-09-08 |
JP6301841B2 (ja) | 2018-03-28 |
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