WO2018186489A1 - フタロシアニン系化合物、及びその用途 - Google Patents
フタロシアニン系化合物、及びその用途 Download PDFInfo
- Publication number
- WO2018186489A1 WO2018186489A1 PCT/JP2018/014746 JP2018014746W WO2018186489A1 WO 2018186489 A1 WO2018186489 A1 WO 2018186489A1 JP 2018014746 W JP2018014746 W JP 2018014746W WO 2018186489 A1 WO2018186489 A1 WO 2018186489A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compound
- phthalocyanine compound
- resin
- heat ray
- Prior art date
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- -1 Phthalocyanine compound Chemical class 0.000 title claims abstract description 330
- 229910052751 metal Inorganic materials 0.000 claims abstract description 27
- 239000002184 metal Substances 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 239000005340 laminated glass Substances 0.000 claims description 80
- 239000000463 material Substances 0.000 claims description 65
- 239000011229 interlayer Substances 0.000 claims description 45
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000011358 absorbing material Substances 0.000 claims description 16
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 4
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 3
- 229920005989 resin Polymers 0.000 abstract description 95
- 239000011347 resin Substances 0.000 abstract description 95
- 238000004519 manufacturing process Methods 0.000 abstract description 34
- 238000010521 absorption reaction Methods 0.000 abstract description 31
- 239000003960 organic solvent Substances 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 description 118
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 238000000862 absorption spectrum Methods 0.000 description 36
- 238000012360 testing method Methods 0.000 description 36
- 229910052739 hydrogen Inorganic materials 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 229920006391 phthalonitrile polymer Polymers 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
- 239000010410 layer Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 238000000034 method Methods 0.000 description 19
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- 238000001228 spectrum Methods 0.000 description 16
- 238000010586 diagram Methods 0.000 description 15
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- 238000004458 analytical method Methods 0.000 description 14
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- 239000000843 powder Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
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- 238000002360 preparation method Methods 0.000 description 12
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 11
- TZCNGVKAONSZKZ-UHFFFAOYSA-N 1-imino-4,7-bis(4-methoxybutyl)benzo[e]isoindol-3-amine Chemical compound COCCCCC1=C2C(NC(C2=C2C(=C1)C=C(C=C2)CCCCOC)=N)=N TZCNGVKAONSZKZ-UHFFFAOYSA-N 0.000 description 10
- 238000000465 moulding Methods 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 229910021551 Vanadium(III) chloride Inorganic materials 0.000 description 5
- 239000006096 absorbing agent Substances 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 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 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
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- 239000002244 precipitate Substances 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- HQYCOEXWFMFWLR-UHFFFAOYSA-K vanadium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[V+3] HQYCOEXWFMFWLR-UHFFFAOYSA-K 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
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- 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 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
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- 239000002216 antistatic agent Substances 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
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- 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
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- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- ZHXZNKNQUHUIGN-UHFFFAOYSA-N chloro hypochlorite;vanadium Chemical compound [V].ClOCl ZHXZNKNQUHUIGN-UHFFFAOYSA-N 0.000 description 1
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- 238000001831 conversion spectrum Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ILHIHKRJJMKBEE-UHFFFAOYSA-N hydroperoxyethane Chemical compound CCOO ILHIHKRJJMKBEE-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- PSCMQHVBLHHWTO-UHFFFAOYSA-K indium(iii) chloride Chemical compound Cl[In](Cl)Cl PSCMQHVBLHHWTO-UHFFFAOYSA-K 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- HWSZZLVAJGOAAY-UHFFFAOYSA-L lead(II) chloride Chemical compound Cl[Pb]Cl HWSZZLVAJGOAAY-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
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- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 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 1
- 238000012015 optical character recognition Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 125000005461 organic phosphorous group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
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- 229920006267 polyester film Polymers 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10614—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer comprising particles for purposes other than dyeing
- B32B17/10633—Infrared radiation absorbing or reflecting agents
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0671—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/073—Preparation from isoindolenines, e.g. pyrrolenines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/226—Glass filters
Definitions
- the present invention relates to a novel phthalocyanine compound having good organic solvent solubility and resin compatibility, excellent visible light transparency and high durability, and uses thereof. Specifically, it has strong absorption in the near infrared region, very little absorption in the visible light region, little coloring, high durability against light and heat, good solubility in organic solvents and resins, near infrared
- the present invention relates to a novel phthalocyanine compound that can be widely used for near-infrared absorbing materials such as absorption filters, security inks, heat ray shielding films, interlayer films for laminated glass, and infrared thermosensitive recording materials, and uses thereof.
- near-infrared absorbing materials have come to be used in a wide range of fields such as optical recording media, near-infrared photosensitizers, photothermal conversion agents, near-infrared cut filters, near-infrared absorbing inks, and heat ray shielding materials.
- optical recording media near-infrared photosensitizers, photothermal conversion agents, near-infrared cut filters, near-infrared absorbing inks, and heat ray shielding materials.
- near-infrared cut filters used in plasma displays
- transparent ink used for security transparent ink used for security
- heat ray shielding materials used in automobiles and building windows
- plastic laser welding etc.
- Cyanine dyes (Reference 1), diimmonium salt dyes (Reference 2), and dithiol nickel complexes (Reference 3) are used because near-infrared absorbing materials have low absorption in the visible light region.
- the cyanine dye has a high near-infrared absorbing ability, it has a low durability and has a problem that an organic solvent to be dissolved is limited to a polar solvent.
- the diimmonium salt dye has a problem that both near-infrared absorption ability and durability are low, and an organic solvent to be dissolved is limited to a polar solvent. Similar problems have been pointed out with dithiol nickel complexes, and there are also problems with their safety.
- Phthalocyanine compounds have also been studied because of their high durability, and phthalocyanine compounds that suppress association in the resin (Document 4) have been proposed, but improvements are desired in terms of resin compatibility. Phthalocyanine compounds similar to the present invention (References 5 and 6) have also been proposed, but the visible transmittance, organic solvent solubility, and resin compatibility are still insufficient, and improvements are desired.
- An object of the present invention is to provide a novel phthalocyanine compound having strong absorption in the near-infrared region, extremely low absorption in the visible light region, high durability, good organic solvent solubility and resin solubility, and the like It is providing the infrared rays absorption material containing this.
- the present invention (I) a phthalocyanine compound represented by the following general formula (1):
- R represents an alkyl group or an aryl group
- X represents a hydrogen atom, a halogen atom or an alkyl group, and may combine with each other to form an aromatic ring.
- M represents two hydrogen atoms, a divalent metal, or a trivalent or tetravalent metal derivative, and n represents an integer of 3 to 6.
- (Ii) The phthalocyanine compound of (i), wherein R is a branched or straight chain alkyl group having 1 to 12 carbon atoms.
- M is two hydrogen atoms, Pd, Cu, Zn, Pt, Ni, TiO, Co, Fe, Mn, Sn, Al—Cl, VO or In, (i) or (ii) phthalocyanine Compounds.
- (Iv) The phthalocyanine compounds of (i) to (iii), wherein R is a methyl group or an ethyl group, X is a hydrogen atom, and n is an integer of 4.
- (V) A near-infrared absorbing material containing the phthalocyanine compound according to any one of (i) to (iv).
- (Vi) A heat ray shielding material containing the phthalocyanine compound according to any one of (i) to (iv).
- (Vii) The heat ray shielding material according to (vi), which is a heat ray shielding film.
- (Viii) The heat ray shielding material according to (vii), which is an interlayer film for laminated glass.
- a phthalocyanine compound having strong absorption in the near infrared region, very small absorption in the visible light region, high durability, and good solubility in organic solvents and resins, and such characteristics It has become possible to provide such applications as near infrared absorbing materials.
- FIG. 2 is an absorption spectrum diagram of compound (1) -30 produced in Example 1.
- FIG. 4 is an absorption spectrum diagram of compound (1) -33 produced in Example 2.
- FIG. 4 is an absorption spectrum diagram of compound (1) -37 produced in Example 3.
- FIG. 4 is an absorption spectrum diagram of compound (1) -39 produced in Example 4.
- FIG. 6 is an absorption spectrum diagram of compound (1) -42 produced in Example 5.
- FIG. 6 is an absorption spectrum diagram of compound (1) -43 produced in Example 6.
- FIG. FIG. 6 is an absorption spectrum diagram of the compound (1) -44 produced in Example 7.
- 6 is an absorption spectrum diagram of compound (1) -38 produced in Example 8.
- FIG. 6 is an absorption spectrum diagram of compound (1) -31 produced in Example 9.
- FIG. 2 is an absorption spectrum diagram of compound (1) -40 produced in Example 10.
- FIG. 2 is an absorption spectrum diagram of compound (1) -45 produced in Example 11.
- FIG. 2 is an absorption spectrum diagram of compound (1) -32 produced in Example 12.
- FIG. 2 is an absorption spectrum diagram of the compound produced in Comparative Example 1.
- FIG. 2 is an absorption spectrum diagram of the compound produced in Comparative Example 2.
- FIG. 2 is a comparison diagram of transmission spectra of compound (1) -30 produced in Example 1, compound (1) -37 produced in Example 3, and compounds produced in Comparative Example 1 and Comparative Example 2.
- the first invention of the present invention is a phthalocyanine compound represented by the general formula (1).
- R represents an alkyl group or an aryl group
- X represents a hydrogen atom, a halogen atom or an alkyl group, and may combine with each other to form an aromatic ring.
- M represents two hydrogen atoms, a divalent metal, or a trivalent or tetravalent metal derivative, and n represents an integer of 3 to 6.
- M is preferably two hydrogen atoms, Pd, Cu, Zn, Pt, Ni, TiO, Co, Fe, Mn, Sn, Al—Cl, VO, or In. More preferably, M is two hydrogen atoms, Pd, Cu, Zn or VO. Most preferred M is Cu or VO.
- R being an alkyl group an alkyl group having 1 to 12 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms is more preferable.
- alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, 1-methylbutyl, 2-methylbutyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 4-methyl- 2-pentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, n-heptyl group, 1-methyl
- alkyl group having a substituent examples include, for example, methoxymethyl group, ethoxymethyl group, n-butoxymethyl group, n-hexyloxymethyl group, (2-ethylbutyloxy) methyl group, 2- ( An alkyl group having an alkyloxy group or an alkenyloxy group, such as a 4′-pentenyloxy) ethyl group, for example, an alkyl group having an aralkyloxy group, such as a benzyloxymethyl group or 2- (benzyloxymethoxy) ethyl group, Alkyl groups having an aryloxy group such as a phenyloxymethyl group, a 4-chlorophenyloxymethyl group, a 4- (2′-phenyloxyethoxy) butyl group, such as an n-butylthiomethyl group, 2-n-octylthio An alkyl group having a thioalkyl group such as an ethoxymethyl
- R being an aryl group
- a phenyl group, a naphthyl group, and a pyridyl group are preferable, and a substituted phenyl group is particularly preferable.
- aryl groups include phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3-ethylphenyl, 4-ethylphenyl, 4-n-propylphenyl, 4-isopropyl Phenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 4- n-hexylphenyl group, 4-cyclohexylphenyl group, 4-n-heptylphenyl group, 4-n-octylphenyl group, 4-n-nonylpheny
- X is an alkyl group, it is synonymous with R in the above-mentioned general formula (1), and its illustration is also the same.
- X is a halogen atom, a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom are mentioned, a chlorine atom and a fluorine atom are preferable, and a fluorine atom is more preferable.
- n is preferably from 4 to 6, and particularly preferably 4. Specific examples of the phthalocyanine compound represented by the general formula (1) are shown in Table 1 below, but are not limited thereto.
- the phthalocyanine compound represented by the general formula (1) can be produced by referring to a known method. That is, a reaction between at least one phthalonitrile compound represented by the general formula (2) or 1,3-diiminoisone indoline compound selected from the general formula (3) and a metal or a metal derivative. By doing so, the phthalocyanine compound of the general formula (1) can be produced.
- metals or metal derivatives examples include Al, Si, Ti, V, Mn, Fe, Co, Ni, Cu, Zn, Ge, Ru, Rh, Pd, In, Sn, Pt, Pb, and their halides and carboxylates. , Sulfates, nitrates, carbonyl compounds, oxides, complexes and the like. In particular, metal halides or carboxylates are preferably used. Examples of these include copper chloride, copper bromide, copper iodide, nickel chloride, nickel bromide, nickel acetate, cobalt chloride, iron chloride, zinc chloride, odor.
- Examples thereof include zinc iodide, zinc iodide, zinc acetate, vanadium chloride, vanadium oxychloride, palladium chloride, palladium acetate, aluminum chloride, manganese chloride, lead chloride, lead acetate, indium chloride, titanium chloride, tin chloride and the like.
- the amount of the metal or metal derivative used is from 0.1 times mol to 0 mol per 1 mol of the phthalonitrile compound of general formula (2) or 1 mol of the 1,3-diiminoisone indoline compound of general formula (3). .6 times mol, preferably 0.2 times mol to 0.5 times mol.
- the reaction temperature is 60 to 300 ° C, preferably 100 to 220 ° C.
- the reaction time is 30 minutes to 72 hours, preferably 1 hour to 48 hours.
- a solvent it is preferable to use a solvent.
- the solvent used for the reaction is preferably an organic solvent having a boiling point of 60 ° C. or higher, preferably 80 ° C. or higher.
- Examples include methanol, ethanol, n-propyl alcohol, n-butyl alcohol, isobutyl alcohol, n-amyl alcohol, n-hexanol, 1-heptanol, 1-octanol, 1-dodecanol, benzyl alcohol, ethylene glycol, propylene glycol, ethoxy Alcohol solvents such as ethanol, propoxyethanol, butoxyethanol, dimethylethanol, diethylethanol, dichlorobenzene, trichlorobenzene, chloronaphthalene, sulfolane, nitrobenzene, quinoline, DMI (1,3-dimethyl-2-imidazolidinone), urea, etc. Of high boiling point solvents.
- the amount of the solvent used is 0.5 to 50 times, preferably 1 to 15 times the volume of the phthalonitrile compound of the general formula (2) or the 1,3-diiminoison indoline compound of the general formula (3). .
- the reaction is carried out in the presence or absence of a catalyst, but is preferably in the presence of a catalyst.
- the catalyst include inorganic catalysts such as ammonium molybdate, DBU (1,8-diazabicyclo [5.4.0] undec-7-ene), DBN (1,5-diazabicyclo [4.3.0] non-5.
- Basic organic catalysts such as -ene) can be used.
- the amount used is 0.01 to 10 times mol, preferably 1 to 2 times mol for 1 mol of phthalonitrile compound or 1 mol of 1,3-diiminoisondrine compound.
- the phthalocyanine compound represented by the general formula (2) or the 1,3-diiminoisone indoline compound represented by the general formula (3) is selected. It can be produced by reacting at least one kind with metal sodium or metal potassium under the above reaction conditions, and then removing sodium or potassium as the central metal with hydrochloric acid, sulfuric acid or the like.
- the solvent is distilled off or the reaction solution is discharged into a poor solvent for the phthalocyanine compound to precipitate the target product, and the precipitate is filtered to obtain the phthalocyanine compound of the general formula (1) I can do it.
- the phthalocyanine compound is obtained as a mixture of isomers.
- further purification by a known purification method such as recrystallization or column chromatography can yield a higher-purity target product.
- the phthalonitrile compound represented by the general formula (2) can be produced by referring to a method known per se. For example, it can be produced by the following route with reference to JP-T-2003-516421.
- X has the same meaning as in the general formulas (2) and (3).
- R 1 represents an alkyl group or an aryl group.
- R in general formula (7) has the same meaning as in general formula (2) and general formula (3), and Y in general formula (7) is a halogen atom.
- an alkylsulfonic acid chloride or arylsulfonic acid chloride of general formula (5) is reacted with a phthalonitrile compound of general formula (4) in the presence of a base in an organic solvent.
- a phthalonitrile-based compound can be produced.
- the alkyl sulfonic acid chloride methane sulfonic acid chloride, ethane sulfonic acid chloride, propane sulfonic acid chloride, trifluoromethane sulfonic acid chloride and the like can be used.
- aryl sulfonic acid chloride benzene sulfonic acid chloride, toluene sulfonic acid chloride, chlorobenzene sulfonic acid chloride, naphthalene sulfonic acid chloride and the like can be used.
- the amount of alkyl sulfonic acid chloride or aryl sulfonic acid chloride used is 2 to 4 times mol, preferably 2 to 3 times mol, more preferably 1 mol to 1 mol of the phthalonitrile compound of general formula (4). It is 2-fold mole to 2.2-fold mole.
- As the base sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, triethylamine, pyridine and the like can be used.
- the amount of the base used is 2 to 4 times mol, preferably 2 to 3 times mol, per 1 mol of the phthalonitrile compound of the general formula (4).
- the solvent is not particularly limited as long as it does not adversely influence the reaction, and dichloromethane, 1,2-dichloroethane, benzotrifluoride, acetonitrile, toluene and the like can be used.
- the amount of the solvent used is not particularly limited, it is 500 mL to 3.0 L, preferably 1.0 to 2.0 L with respect to 1 mol of the phthalonitrile compound.
- the reaction temperature is room temperature to 200 ° C, preferably 50 to 150 ° C, more preferably 50 to 100 ° C.
- the reaction time is 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 30 minutes to 12 hours.
- the solvent is distilled off or the reaction solution is discharged into a poor solvent for the phthalonitrile compound to precipitate the target product, and the precipitate is filtered to obtain the phthalonitrile compound of the general formula (6).
- a higher-purity product can be obtained by further adding known purification operations such as recrystallization and column chromatography to the product.
- the phthalonitrile compound of the general formula (6) is cross-coupled (Negishi reaction) with the organic zinc reagent of the general formula (7) in the presence of a palladium catalyst in an organic solvent in the presence of a palladium catalyst.
- Y is chlorine, bromine, iodine, or fluorine, preferably chlorine, bromine, or more preferably bromine.
- the amount of the organozinc reagent used is 2 to 5 times, preferably 2 to 3 times the mol of 1 mol of the phthalonitrile compound of the general formula (6).
- the amount of the palladium catalyst to be used is 0.01 to 0.3 equivalent, preferably 0.05 to 0.2 equivalent, relative to 1 mol of the phthalonitrile compound of the general formula (6).
- reaction solvent tetrahydrofuran, diethyl ether, 1,4-dioxane and the like can be used.
- the amount of the reaction solvent to be used is not particularly limited, but is 500 mL to 3.0 L, preferably 1.0 to 2.0 L, with respect to 1 mol of the phthalonitrile compound of the general formula (6).
- the reaction temperature is room temperature to 200 ° C, preferably 50 to 150 ° C, more preferably 50 to 100 ° C.
- the reaction time is 10 minutes to 48 hours, preferably 20 minutes to 24 hours, more preferably 30 minutes to 12 hours.
- the solvent is distilled off, extraction is performed with an aromatic solvent such as toluene or a halogenated hydrocarbon solvent such as methylene chloride, the extract is washed with water, concentrated, and a poor solvent is added to the concentrate for the purpose.
- the phthalonitrile compound of the general formula (2) can be obtained by precipitating the product and filtering the precipitate. If necessary, a higher-purity product can be obtained by further adding known purification operations such as recrystallization and column chromatography to the product.
- the 1,3-diiminobenzoindoline compound represented by the general formula (3) can be produced by referring to a known method relating to a known compound. For example, it is produced by reacting a phthalonitrile compound represented by the general formula (2) and ammonia in the presence of a metal alkoxide.
- the amount of ammonia used is 1 to 20 times mol, preferably 3 to 10 times mol, per 1 mol of the phthalonitrile compound of the general formula (2).
- Metal alkoxides include sodium or potassium methoxide, ethoxide, n-propoxide, n-butoxide, n-pentoxide, n-hexyloxyside, n-octyloxyside, 2-methoxyethoxide, 2-ethoxyethoxide 2-butoxyethoxide is used.
- the metal alkoxide is used in an amount of 0.01 to 5 times, preferably 0.1 to 2.0 times the mol of the phthalonitrile compound of the general formula (2).
- an organic solvent is preferably used in combination, and an alcohol solvent is usually used as the organic solvent.
- alcohol solvents include methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol, n-heptanol, n-octanol, 2-methoxyethanol, 2-ethoxyethanol, and 2-butoxyethanol.
- the amount of the alcohol solvent used is 200 mL to 15 L, preferably 500 mL to 5 L, per 1 mol of the phthalonitrile compound of the general formula (2).
- the reaction is carried out by charging ammonia and a phthalonitrile compound of the general formula (2).
- ammonia, a phthalonitrile compound of the general formula (2), and a separately prepared metal alkoxide may be charged into a reaction solvent for reaction.
- the amount of the metal used for adjusting the metal alkoxyside is 0.01 to 5.0 times mol, preferably 0.1 to 2.0 times mol for the phthalonitrile compound of the general formula (2). It is.
- the reaction temperature is 0 ° C. to the reflux temperature of the solvent, preferably 20 ° C. to the reflux temperature of the solvent.
- the reaction time is preferably 30 minutes to 72 hours.
- the solvent is distilled off, extracted with an aromatic solvent such as toluene or a halogenated hydrocarbon solvent such as methylene chloride, the extract is washed with water, concentrated, and the precipitate is filtered.
- the 1,3-diiminobenzoindoline compound (3) can be obtained.
- the phthalocyanine compound of the present invention is a heat ray shielding material for shielding heat rays, an optical filter for plasma display or liquid crystal display, a flash heat fixing toner, a photothermal exchange agent for thermal transfer / thermal stencil, photothermal conversion for laser fusion, etc.
- a heat ray shielding material for shielding heat rays
- an optical filter for plasma display or liquid crystal display for plasma display or liquid crystal display
- a flash heat fixing toner a photothermal exchange agent for thermal transfer / thermal stencil
- photothermal conversion for laser fusion etc.
- the near-infrared absorbing material of the present invention may be the phthalocyanine compound of the present invention represented by the general formula (1) itself, or a phthalocyanine of the general formula (1) together with other components such as a binder resin and additives. It may contain a compound.
- the modes and components of the near infrared absorbing material vary depending on the application and are various.
- the heat ray shielding material of this invention is demonstrated.
- the phthalocyanine compound of the present invention is suitably used for heat ray shielding materials used for films and interlayers used in buildings, automobile windows, etc., vinyl houses, sun visors, welding goggles and the like.
- the heat ray shielding material of the present invention contains the phthalocyanine compound of the present invention represented by the general formula (1).
- the phthalocyanine compound of the general formula (1) contained in the heat ray shielding material of the present invention may be used as a single compound or in the form of a mixture of two or more.
- the usage form of the heat ray shielding material of the present invention is not particularly limited, and may be any known form.
- Specific examples include the following examples. 1.
- Form using molded body itself containing phthalocyanine compound of general formula (1) and resin as essential components Form in which coating film or film containing phthalocyanine compound of general formula (1) and resin as essential components is applied on a base material 3. Between two or more base materials, phthalocyanine of general formula (1) 3.
- the base material in which the phthalocyanine compound of the general formula (1) is included in the base material is not particularly limited, but is a glass plate; polycarbonate, polymethyl methacrylate, polystyrene, polyethylene terephthalate, polyvinyl chloride, polysulfone, Examples thereof include a plastic plate such as a plate material of unsaturated polyester. Among the above forms, in particular 2.
- middle layer is preferable.
- the aspect which contains the phthalocyanine type compound and resin of General formula (1) as an essential component is preferable for the heat ray shielding material of this invention.
- the resin can be appropriately selected depending on the intended use of the heat ray shielding material, but is preferably a resin that is substantially transparent and does not significantly absorb and scatter.
- polycarbonate resin such as methyl methacrylate
- polyvinyl resin such as polystyrene, polyvinyl chloride, and polyvinylidene chloride
- polyolefin resin such as polyethylene and polypropylene
- polybutyral resin acetic acid such as polyvinyl acetate
- vinyl resins polyester resins; polyamide resins; polyvinyl acetal resins; polyvinyl alcohol resins; ethylene-vinyl acetate copolymer resins; ethylene-acrylic copolymer resins;
- it is substantially transparent, not only the above-mentioned one kind of resin but also a blend of two or more kinds of resins can be used, and the above resin can be sandwiched between transparent glasses. .
- polycarbonate resin (meth) acrylic resin, polyester resin, polyamide resin, polystyrene resin, polyvinyl chloride resin, polyvinyl acetal resin, and polyvinyl alcohol resin are preferable, and polycarbonate resin, methacrylic resin, polyethylene terephthalate (PET) are particularly preferable.
- PBT polyethylene terephthalate
- Resin, polyvinyl chloride resin, and polyvinyl acetal resin are more preferable.
- the polycarbonate resin is produced by reacting a dihydric phenol and a carbonate precursor by a solution method or a melting method.
- dihydric phenol 2,2-bis (4-hydroxyphenyl) propane [bisphenol A], 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) cyclohexane, 2,2-bis (4 -Hydroxy-3,5-dimethylphenyl) propane, 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane, 2,2-bis (4-hydroxy-3-methylphenyl) propane, bis ( 4-hydroxyphenyl) sulfide, bis (4-hydroxyphenyl) sulfone, and the like.
- Preferred divalent phenols are bis (4-hydroxyphenyl) alkanes, particularly those containing bisphenol as the main component.
- (Meth) acrylic resin includes methyl methacrylate alone, a polymerizable unsaturated monomer mixture containing 50% or more of methyl methacrylate, or a copolymer thereof.
- Examples of the polymerizable unsaturated monomer copolymerizable with methyl methacrylate include the following.
- polyester resins include homopolyesters such as poly C2-4 alkylene terephthalate and poly C2-4 alkylene naphthalate, C2-4 alkylene arylate units (C2-4 alkylene terephthalate and / or C2-4 alkylene naphthalate units).
- polyarylate resins aliphatic polyesters using aliphatic dicarboxylic acids such as adipic acid, and lactone homo- or copolymers such as ⁇ -caprolactone are also included.
- polyester resin polyethylene terephthalate (PET), polytrimethylene terephthalate (PTT), polybutylene terephthalate (PBT), polyethylene naphthalate (PEN) and the like are preferable in terms of high transparency.
- Amorphous copolyesters such as C2-4 alkylene arylate copolyesters are also preferred because of their excellent processability.
- PET is preferable because it is produced in large quantities and is excellent in heat resistance and strength.
- the polyamide resin is a resin having a dehydration polycondensate structure of a diamine compound containing an aromatic or aliphatic group and a dicarboxylic acid compound containing an aromatic or aliphatic group.
- the aliphatic group also includes an alicyclic aliphatic group.
- diamine compounds include hexamethylenediamine, m-xylylenediamine, bis (4-aminocyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane, trimethylhexamethylenediamine, bis (aminomethyl) norbornane, Examples thereof include bis (aminomethyl) tetrahydrodicyclopentadiene.
- dicarboxylic acid compounds examples include adipic acid, dodecanedicarboxylic acid, isophthalic acid, terephthalic acid, bis (hydroxycarbonylmethyl) norbornane, bis (hydroxycarbonylmethyl) tetrahydrodicyclopentadiene, and the like.
- the polyamide resin an amorphous polyamide resin is particularly preferable from the viewpoint of transparency, and resins generally referred to as transparent nylon are preferable.
- the polyvinyl chloride resin not only a polymer of vinyl chloride monomer but also a copolymer mainly composed of vinyl chloride can be used. Examples of monomers that can be copolymerized with vinyl chloride include vinylidene chloride, ethylene, propylene, acrylonitrile, vinyl acetate, maleic acid, itaconic acid, acrylic acid, and methacrylic acid.
- polyvinyl acetal resin examples include a polyvinyl formal resin obtained by reacting polyvinyl alcohol (PVA) and formaldehyde, a narrowly defined polyvinyl acetal resin obtained by reacting PVA and acetaldehyde, and a reaction between PVA and n-butyraldehyde.
- Polyvinyl butyral resin (PVB) obtained by the above, and PVB is preferable.
- the PVA used for the synthesis of the polyvinyl acetal resin preferably has an average degree of polymerization of 200 to 5000, more preferably 500 to 3000.
- the acetalization degree is preferably 40 to 85 mol%, more preferably 50 to 75 mol%.
- the polyvinyl alcohol resin can be obtained, for example, by saponifying polyvinyl acetate.
- the degree of saponification of the polyvinyl alcohol resin is generally in the range of 70 to 99.9 mol%, preferably in the range of 75 to 99.8 mol%, and in the range of 80 to 99.8 mol%. It is more preferable.
- the average degree of polymerization of the polyvinyl alcohol resin is preferably 500 or more, more preferably 1000 or more and 5000 or less.
- the content of the tetraphenylnaphthalocyanine compound of the present invention represented by the general formula (1) in the heat ray shielding material of the present invention varies depending on the thickness of the heat ray shielding material.
- 0.002 to 0.06 parts by weight is preferable with respect to 100 parts by weight of the resin blended in the heat ray shielding material, and more preferably 0.003 to 0.02 part by weight.
- a heat ray shielding plate having a thickness of 10 mm is produced, 0.0005 to 0.02 parts by weight is preferable with respect to 100 parts by weight of the resin, and more preferably 0.001 to 0.005 parts by weight. It is.
- the amount is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 10 parts by weight with respect to 100 parts by weight of the resin.
- the content of the phthalocyanine compound of the general formula (1) is expressed regardless of the thickness of the heat ray shielding material, it is considered to be the weight in the projected area from above, and is 0.01 to 5.0 g / m 2 .
- the blending amount is preferable, and 0.05 to 1.0 g / m 2 is more preferable.
- the blending amount of the phthalocyanine compound of the general formula (1) is less than 0.01 g / m 2 , the heat ray shielding effect is reduced, and when it exceeds 5.0 g / m 2 , visible light transmission is reduced. There is a case.
- the heat ray shielding material of the present invention may contain various additives that are used when producing ordinary transparent resin materials.
- the additive include a colorant, a polymerization regulator, an antioxidant, an ultraviolet absorber, a heat ray shielding agent, a flame retardant, a plasticizer, a rubber for improving impact resistance, and a release agent.
- the heat ray shielding agent means particles capable of absorbing infrared rays having a wavelength of 780 nm or more, and includes aluminum-doped tin oxide, indium-doped tin oxide, tin-doped indium oxide (ITO), antimony-doped tin oxide (ATO), and aluminum.
- the heat ray shielding agent is not particularly limited, but is usually 10% by mass or less in the heat ray shielding material.
- an ultraviolet absorber it does not restrict
- the heat ray shielding material of the present invention may contain other near infrared ray absorbing materials.
- the other near-infrared absorbing material is not particularly limited, and a known near-infrared absorbing material can be appropriately selected depending on the maximum absorption wavelength desired depending on the application.
- the shape of the heat ray shielding material is not particularly limited, and includes various shapes such as a corrugated plate shape, a spherical shape, and a dome shape in addition to the most common flat plate shape and film shape.
- the heat ray shielding material of the present invention is in the form of a flat plate or a film
- the phthalocyanine compound of the general formula (1) is mixed with the resin and, if necessary, the additive and other near infrared absorbing materials, and then molded.
- a heat ray shielding material is obtained.
- the molding method is not particularly limited, and a known molding method can be applied. Specific examples include extrusion molding, injection molding, cast polymerization, press molding, calender molding, or cast film forming method.
- the use form of the heat ray shielding material of the present invention is a form in which a film containing a phthalocyanine compound of the general formula (1) and a resin as essential components is applied on a base material, an adhesive, It can be applied by sticking a film or sheet-like heat ray shielding material using an adhesive, an adhesive film, or the like.
- a heat ray shielding material in the form of a film or a sheet can be applied to the substrate by hot pressing or hot lamination molding.
- the use form of the heat ray shielding material of the present invention is a form in which a coating film containing a phthalocyanine compound of the general formula (1) and a resin as essential components is applied on a substrate, the phthalocyanine of the general formula (1) It can be applied by preparing a paint (liquid or paste) containing a compound and resin and, if necessary, a solvent for dissolving them and other components, and coating the paint on a substrate it can.
- the use form of the heat ray shielding material of the present invention is a laminate in which a film containing, as an essential component, a phthalocyanine compound of the general formula (1) and a resin as essential components is provided between two or more substrates.
- a film containing the phthalocyanine compound of the general formula (1) and a resin as essential components is sandwiched between base materials, placed in a rubber pack and sucked under reduced pressure, and then heated and vacuum bonded. can do.
- a phthalocyanine compound of the general formula (1) and a phthalocyanine compound of the general formula (1) and a film containing the resin as essential components are sandwiched between the substrates, or on one of the substrates.
- the use of the heat ray shielding material of the present invention is not particularly limited, and examples thereof include films and interlayer films, sun visors, welding goggles and the like used for buildings, automobile windows, etc. for solar energy heat ray shielding.
- the phthalocyanine compound represented by the general formula (1) of the present invention is excellent in solvent solubility and compatibility with a resin, and excellent in various properties such as heat resistance, light resistance, and weather resistance. It is suitable as a film or an intermediate film used for a window or the like.
- Heat ray shielding film The case where the heat ray shielding material of the present invention is a heat ray shielding film used by being attached to a window glass or the like of a building will be described below. Although there is no restriction
- Embodiment 2 which is a film containing a phthalocyanine compound of general formula (1) and a resin
- Aspect 3 which is a mode having a film containing a phthalocyanine compound of the general formula (1) and a resin, a pressure-sensitive adhesive layer, and a release sheet provided on the surface of the pressure-sensitive adhesive layer as necessary.
- an embodiment having an adhesive layer is preferred, and in particular, 4. Or 5. This embodiment is preferred.
- further layers such as a hard coat layer, an antifouling layer, an ultraviolet absorbing layer, and an antireflection layer may be provided depending on the purpose.
- Examples of the resin contained together with the phthalocyanine compound of the general formula (1) include the same resins as those of the resin contained in the heat ray shielding material.
- polycarbonate resin, (meth) acrylic resin, polyvinyl resin, polyolefin resin, polybutyral resin, polyester resin, polyamide resin, and polyurethane resin are preferable.
- Examples of the base material include those similar to the examples of the base material described in the use form of the heat ray shielding material, but a resin sheet or plate is preferable.
- Examples thereof include films of polyester, polyethylene, polypropylene, nylon, polyvinyl chloride, polycarbonate, polyvinyl alcohol, polymethyl methacrylate, fluororesin, ethylene, vinyl alcohol resin, and the like.
- a polyester film is preferable, and a polyethylene terephthalate (PET) film is more preferable.
- the pressure-sensitive adhesive is not particularly limited as long as it can be adhered to a substrate and has transparency.
- Examples thereof include rubber adhesives.
- Examples of the resin that is a pressure-sensitive adhesive include the above-mentioned thermoplastic, thermosetting, and active energy ray-curable curable resin pressure-sensitive adhesives, but (meth) acrylic resins are preferable, and the glass transition temperature is less than 0 ° C. Poly (meth) acrylic acid ester resins are particularly preferred.
- the poly (meth) acrylate resin is preferably one using 50% by weight or more of (meth) acrylate ester having an alkyl group having 1 to 14 carbon atoms as a monomer.
- copolymerizable monomers include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate and the like ( (Meth) acrylates; styrene monomers represented by ⁇ -methylstyrene, vinyltoluene, styrene, etc .; vinyl ether monomers represented by methyl vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, etc .; fumaric acid, fumaric acid Monoalkyl ester, dialkyl ester of fumaric acid; maleic acid, mono
- an isocyanate curing agent As the curing agent for the acrylic adhesive, an isocyanate curing agent, an epoxy curing agent, a metal chelate curing agent, or the like is used.
- Each layer of the heat ray shielding film may contain the same additives as those used in the production of the heat ray shielding material. Examples include colorants, polymerization regulators, antioxidants, light stabilizers, ultraviolet absorbers, flame retardants, antistatic agents, plasticizers, and the like.
- an embodiment containing an ultraviolet absorber is preferred, such as an antioxidant, a flame retardant, an adhesive strength modifier, a moisture-resistant agent, a fluorescent brightening agent, and an infrared absorber.
- the thickness of the heat ray shielding film varies depending on the configuration, the type of resin of the base material and the heat ray shielding layer, the use thereof, and the like, but usually about 10 ⁇ m to 500 ⁇ m is preferably used.
- the thickness of the base material is preferably about 20 ⁇ m to 300 ⁇ m.
- the thickness of the layer containing the phthalocyanine compound of the general formula (1) and the resin is preferably about 0.3 to 100 ⁇ m.
- the content of the phthalocyanine compound of the general formula (1) relative to the resin depends on the thickness of the layer containing the phthalocyanine compound of the general formula (1) and the resin.
- the phthalocyanine compound 1) is preferably in the range of 0.001 to 30 parts by weight, more preferably in the range of 0.01 to 10 parts by weight.
- the phthalocyanine compound and resin of the general formula (1) are mixed with the above additives, other near-infrared absorbers and ultraviolet absorbers as necessary, and then molded.
- the molding method is not particularly limited, and a known molding method can be applied as it is or appropriately modified. Specifically, extrusion molding, injection molding, cast polymerization, press molding, calender molding, cast film formation, or the like can be suitably used. Furthermore, it can also be produced by preparing a resin film containing the phthalocyanine compound of the general formula (1) and hot pressing or heat laminating the film to the resin material. It can also be produced by printing or coating an acrylic resin ink or paint containing a phthalocyanine compound of the general formula (1) on a resin material.
- the interlayer film for laminated glass is a resin film used in a form sandwiched between two sheets of glass.
- a phthalocyanine-based compound of the general formula (1) Contains compound and resin as essential components.
- the resin is not particularly limited as long as it has sufficient visibility when used for laminated glass, and preferably has a visible light transmittance of 70% or more when laminated glass is used.
- polyvinyl acetal resins for example, polyvinyl acetal resins, polyvinyl chloride resins, saturated polyester resins, polyurethane resins, ethylene-vinyl acetate copolymer resins, ethylene-ethyl acrylate copolymer resins, and the like have been used for intermediate films.
- the thermoplastic resin which is mentioned.
- a plasticized polyvinyl acetal resin is preferable.
- the polyvinyl acetal resin includes a polyvinyl formal resin obtained by reacting polyvinyl alcohol (PVA) and formaldehyde, a narrowly defined polyvinyl acetal resin obtained by reacting PVA and acetaldehyde, and a reaction between PVA and n-butyraldehyde.
- the polyvinyl butyral resin (PVB) etc. which are obtained by making it include are mentioned, and especially a polyvinyl butyral resin (PVB) is preferable.
- the PVA used for the synthesis of the polyvinyl acetal resin preferably has an average degree of polymerization of 200 to 5000, more preferably 500 to 3000.
- the polyvinyl acetal-based resin preferably has an acetalization degree of 40 to 85 mol%, more preferably 50 to 75 mol%.
- the residual acetyl group content is preferably 30 mol% or less, more preferably 0.5 to 24 mol%.
- the plasticizer used for plasticizing a thermoplastic resin, preferably a polyvinyl acetal resin include, for example, organic acid ester plasticizers such as monobasic organic acid esters and polybasic organic acid esters, Examples thereof include phosphoric acid plasticizers such as organic phosphoric acid and organic phosphorous acid.
- the thickness of the interlayer film for laminated glass varies depending on the type of resin, its use, etc., but is usually preferably in the range of 0.1 to 3 mm, and in the range of 0.3 to 1.5 mm. More preferably.
- the content of the phthalocyanine compound of the general formula (1) with respect to the resin is not particularly limited, but may be within the range of 0.001 to 2 parts by weight of the phthalocyanine compound of the general formula (1) with respect to 100 parts by weight of the resin. Preferably, it is in the range of 0.005 to 0.5 parts by weight.
- the interlayer film for laminated glass of the present invention may contain the same additives as those used in the production of the heat ray shielding material.
- a heat ray shielding agent an ultraviolet absorber, an antioxidant, a light stabilizer, a flame retardant, an antistatic agent, an adhesive force adjusting agent, a moisture resistant agent, a fluorescent brightening agent, a colorant, an infrared absorber, and the like can be given.
- an embodiment containing an ultraviolet absorber is preferable.
- Examples of the method for producing the interlayer film for laminated glass of the present invention include the same methods as those for producing the heat ray shielding material and the heat ray shielding film.
- the interlayer film for laminated glass according to the present invention has at least one of a primer function, an ultraviolet cut function, a flame retardant function, an antireflection function, an antiglare function, an antireflection antiglare function, and an antistatic function as necessary. It is good also as a multilayer structure combined with the functional transparent layer which has a function.
- the laminated glass using the interlayer film for laminated glass of the present invention has a configuration in which the interlayer film of the present invention is sandwiched and bonded and integrated between at least two transparent glass substrates.
- the transparent glass substrate for example, float plate glass, polished plate glass, flat glass, curved plate glass, parallel plate glass, mold plate glass, wire mesh type plate glass, heat ray absorbing plate glass, clear glass, colored glass plate, etc.
- transparent glass substrates include various inorganic glass plates, organic glass plates such as polycarbonate plates and polymethyl methacrylate plates. These transparent glass substrates may be used alone or in combination of two or more kinds.
- the interlayer film of the present invention is sandwiched between two transparent glass substrates and placed in a vacuum bag, and the pressure in the vacuum bag is reduced to about ⁇ 65 to ⁇ 100 kPa. After pre-adhering at a temperature of about 70 to 110 ° C.
- Example 1 Production of phthalocyanine compound (specific example (1) -30) 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline 18.6 g, vanadium trichloride 4.76 g, and DBU 13.74 g in 100 mL of 1-pentanol at an internal temperature of 125 ° C. Stir for hours. 600 mL of methanol was added, and the precipitate was collected by filtration and dried. Purification by column chromatography (silica gel / toluene) gave 14.5 g of dark green powder.
- Example 2 Production of phthalocyanine compound (specific example (1) -33) Instead of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4-ethoxybutyl) -1,3-diiminobenzo Except for using 20.3 g of isoindoline, 14.8 g of a deep green powder was obtained in the same manner as in Example 1. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 3 Production of phthalocyanine compound (specific example (1) -37) Instead of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4-phenoxybutyl) -1,3-diiminobenzo A dark green powder 17.7 g was obtained in the same manner as in Example 1 except that 25.9 g of isoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 4 Production of phthalocyanine compound (specific example (1) -39) Instead of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4- (3-methoxyphenoxy) butyl) -1, 5.9 g of dark green powder was obtained in the same manner as in Example 1 except that 29.4 g of 3-diiminobenzoisoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 5 Production of phthalocyanine compound (specific example (1) -42) 4,7-bis (4- (4- (tert-butyl) phenoxy) butyl in place of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1 ) 13.0 g of dark green powder was obtained in the same manner as in Example 1 except that 32.5 g of 1,3-diiminobenzoisoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 6 Production of phthalocyanine compound (specific example (1) -43) Instead of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4- (2-fluorophenoxy) butyl) -1, Except for using 28.0 g of 3-diiminobenzoisoindoline, 11.2 g of dark green powder was obtained in the same manner as in Example 1. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 7 Production of phthalocyanine compound (specific example (1) -44) 4,7-bis (4- (2,6-dimethoxyphenoxy) butyl)-in place of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1 A dark green powder of 19.7 g was obtained in the same manner as in Example 1 except that 32.9 g of 1,3-diiminobenzoisoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 8 Production of phthalocyanine compound (specific example (1) -38) In place of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4- (2-phenoxyethoxy) butyl) -1, A dark green powder of 14.9 g was obtained in the same manner as in Example 1 except that 31.0 g of 3-diiminobenzoisoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 9 Production of phthalocyanine compound (specific example (1) -31) A dark green powder of 14.9 g was obtained in the same manner as in Example 1 except that 3.00 g of cuprous chloride was used instead of 4.76 g of vanadium trichloride in Example 1. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 10 Production of phthalocyanine compound (specific example (1) -40) 13.5 g of dark green powder was obtained in the same manner as in Example 1 except that 3.00 g of cuprous chloride was used instead of 4.76 g of vanadium trichloride in Example 4. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 11 Production of phthalocyanine compound (specific example (1) -45) A dark green powder 12.1 g was obtained in the same manner as in Example 1 except that 3.00 g of cuprous chloride was used instead of 4.76 g of vanadium trichloride in Example 7. The obtained compound was confirmed to be the target compound from the following analysis results.
- Example 12 Production of phthalocyanine compound (specific example (1) -32) 7.4 g of dark green powder was obtained in the same manner as in Example 1 except that 4.12 g of zinc chloride was used instead of 4.76 g of vanadium trichloride in Example 1. The obtained compound was confirmed to be the target compound from the following analysis results.
- Comparative Example 1 Synthesis of Comparative Example Compound (a) Instead of 18.6 g of 4,7-bis (4-methoxybutyl) -1,3-diiminobenzoisoindoline in Example 1, 4,7-bis (4-methoxymethyl) -1,3-diiminobenzo 9.3 g of a dark green powder was obtained in the same manner as in Example 1 except that 13.7 g of isoindoline was used. The obtained compound was confirmed to be the target compound from the following analysis results.
- the phthalocyanine compounds of the present invention produced in the above examples have high solubility in aromatic organic solvents (for example, benzene, toluene, xylene, mesitylene, etc.). Further, the solubility in polar organic solvents (acetone, ethyl acetate, propylene carbonate, cyclopentanone, etc.) is also high. The solubility in cyclopentanone was measured by the following method. The results are shown in Table 2.
- aromatic organic solvents for example, benzene, toluene, xylene, mesitylene, etc.
- polar organic solvents acetone, ethyl acetate, propylene carbonate, cyclopentanone, etc.
- Solubility (wt%) (W0-W1) / W0 W0: exact weight of phthalocyanine compound before treatment, W1: weight of filtrate after drying (dissolved residue of phthalocyanine compound). When no filter residue remained in the filter, the solubility was 10 wt% or more. All of the compounds of Examples have higher solubility in cyclopentanone than the compounds of Comparative Examples.
- FIG. 15 shows a comparison of transmission spectra of the phthalocyanine compounds of the present invention produced in Example 1 and Example 3 and the compounds of Comparative Examples 1 and 2.
- (Visible light transmittance measurement method) In a 100 mL volumetric flask, 1.000 mg of each phthalocyanine compound and about 90 mL of chloroform were placed, irradiated with ultrasonic waves for 30 minutes, and allowed to stand at room temperature for 2 hours.
- Example 13 Production of heat ray shielding film 5 g of phthalocyanine compound (specific example (1) -30) produced in Example 1, acrylic resin LP-45M (product name, manufactured by Soken Chemical Co., Ltd.) 50 g, methyl ethyl ketone 20 g, 20 g of toluene was mixed and stirred to produce a resin composition.
- the resin composition was coated on a polyethylene terephthalate film (PET film) having a thickness of 100 ⁇ m as a transparent substrate so as to have a thickness of 2.5 ⁇ m, and then dried at 100 ° C. for 3 minutes.
- PET film polyethylene terephthalate film
- Example 14 Production of heat ray shielding film The same as Example 13 except that in Example 13, the compound of Example (1) -33 was used instead of the compound of Example (1) -30 as the phthalocyanine compound. The operation was performed to produce a heat ray shielding film.
- Example 15 Production of heat ray-shielding film The same as Example 13 except that in Example 13, the compound of Example (1) -37 was used instead of the compound of Example (1) -30 as the phthalocyanine compound. The operation was performed to produce a heat ray shielding film.
- Example 16 Production of heat ray-shielding film In Example 13, the compound of Example (1) -39 was used as the phthalocyanine compound instead of the compound of Example (1) -30. The operation was performed to produce a heat ray shielding film.
- Example 17 Production of heat ray-shielding film
- the compound of Example (1) -42 was used as the phthalocyanine compound instead of the compound of Example (1) -30. The operation was performed to produce a heat ray shielding film.
- Example 18 Production of heat ray shielding film The same as Example 13 except that the compound of Example (1) -43 was used as the phthalocyanine compound in Example 13 instead of the compound of Example (1) -30. The operation was performed to produce a heat ray shielding film.
- Example 19 Production of heat ray shielding film
- the compound of Example (1) -44 was used as the phthalocyanine compound instead of the compound of Example (1) -30. The operation was performed to produce a heat ray shielding film.
- Example 20 Production of heat ray shielding film The same as Example 13 except that the compound of Example (1) -38 was used instead of the compound of Example (1) -30 as the phthalocyanine compound in Example 13. The operation was performed to produce a heat ray shielding film.
- Example 21 Production of heat ray-shielding film In Example 13, the compound of Example (1) -31 was used instead of the compound of Example (1) -30 as the phthalocyanine compound, as in Example 13. The operation was performed to produce a heat ray shielding film.
- Example 22 Production of heat ray-shielding film The same as Example 13 except that the compound of Example (1) -40 was used as the phthalocyanine compound instead of the compound of Example (1) -30 in Example 13. The operation was performed to produce a heat ray shielding film.
- Example 23 Production of heat ray shielding film The same as Example 13 except that in Example 13, the compound of Example (1) -45 was used instead of the compound of Example (1) -30 as the phthalocyanine compound. The operation was performed to produce a heat ray shielding film.
- Example 24 Production of heat ray-shielding film The same as Example 13 except that the compound of Example (1) -32 was used instead of the compound of Example (1) -30 as the phthalocyanine compound in Example 13. The operation was performed to produce a heat ray shielding film.
- Example 3 Production of heat ray shielding film
- the compound (a) of Comparative Example 1 was used instead of the compound of Specific Example (1) -30 as the phthalocyanine compound. The operation was performed to produce a heat ray shielding film.
- the following items were evaluated. The results are shown in Table 4 below.
- the peeling film of the manufactured heat ray shielding film was peeled off and pressure-bonded to a glass plate having a thickness of 5 cm ⁇ 5 cm ⁇ 3 mm to prepare a test piece, which was used.
- Tts A U-3500 self-recording spectrophotometer manufactured by Hitachi, Ltd. is used as a measuring instrument, and laminated glass according to JIS R3106 “Testing method for transmittance, reflectance, emissivity, and solar heat gain of plate glass” The Tts of the sample was measured. Tts (Total solar energy transmitted through a glazing) represents the total solar transmittance, and the smaller the value, the higher the heat shielding ability.
- ⁇ (%) ⁇ (400 to 900 nm of E1) ⁇ (400 to E2 900 nm) ⁇ / ⁇ (400 to 900 nm of E1) ⁇ 100
- E1 spectrum before test
- E2 spectrum after test
- ⁇ integration of absorbance values.
- Table 8 all of the heat ray shielding films of the Examples exhibited superior characteristics in terms of heat shielding ability, light resistance and heat resistance as compared with Comparative Examples. In particular, it was very excellent in light resistance and heat resistance.
- Example 25 Preparation of interlayer film for laminated glass and laminated glass ⁇ Preparation of interlayer film for laminated glass>
- 0.013 g of the phthalocyanine compound (specific example (1) -30) produced in Example 1 was dissolved in 40 g of triethylene glycol-di-2-ethylhexanoate.
- polyvinyl butyral resin trade name: BH-3, manufactured by Sekisui Chemical Co., Ltd.
- the above interlayer film is cut into a size of 100 mm ⁇ 100 mm, sandwiched between heat ray absorbing plate glasses (length 100 mm ⁇ width 100 mm ⁇ thickness 2.0 mm) according to JIS R3208, put in a rubber bag, and a vacuum degree of 2.6 kPa After degassing for 20 minutes, it was transferred to an oven while being degassed, and further vacuum-pressed by holding at 90 ° C. for 30 minutes. Then, it pressure-bonded for 20 minutes on the conditions of the temperature of 130 degreeC, and the pressure of 1.3 MPa in the autoclave, and the sample of the laminated glass was obtained.
- Example 26 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same operation was performed except that the phthalocyanine compound was changed to the compound produced in Example 2 (specific example (1) -33). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 27 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same procedure was followed except that the phthalocyanine compound was changed to the compound produced in Example 3 (specific example (1) -37). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 28 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same procedure was followed except that the phthalocyanine compound was changed to the compound produced in Example 4 (specific example (1) -39). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 29 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same operation was performed except that the phthalocyanine compound was changed to the compound produced in Example 5 (specific example (1) -42). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 30 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same procedure was followed except that the phthalocyanine compound was changed to the compound produced in Example 6 (specific example (1) -43). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 31 Preparation of interlayer film for laminated glass and laminated glass In Example 25, the same operation was performed except that the phthalocyanine compound was changed to the compound produced in Example 7 (specific example (1) -44). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 32 Preparation of interlayer film for laminated glass and laminated glass
- Example 25 the same procedure was followed except that the phthalocyanine compound was changed to the compound produced in Example 8 (specific example (1) -38).
- Example 33 Preparation of interlayer film for laminated glass and laminated glass The same operation as in Example 25 was performed except that the phthalocyanine compound was changed to the compound produced in Example 9 (specific example (1) -31).
- Example 9 Specific example (1) -3
- Example 34 Preparation of interlayer film for laminated glass and laminated glass The same operation as in Example 25 was conducted except that the phthalocyanine compound was changed to the compound produced in Example 10 (specific example (1) -40). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 35 Preparation of interlayer film for laminated glass and laminated glass The same operation as in Example 25 was performed except that the phthalocyanine compound was changed to the compound produced in Example 11 (specific example (1) -45). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 36 Production of interlayer film for laminated glass and laminated glass The same operation as in Example 25 was conducted except that the phthalocyanine compound was changed to the compound produced in Example 12 (specific example (1) -32). Thus, an interlayer film for laminated glass and a laminated glass were produced.
- Example 4 Production of interlayer film for laminated glass and laminated glass In Example 25, except that the compound (a) of Comparative Example 1 was used instead of the compound of Specific Example (1) -30 as the phthalocyanine compound. In the same manner as in No. 25, an interlayer film for laminated glass and a laminated glass were produced. The following items were evaluated for the laminated glass samples prepared in Examples 25 to 36 and Comparative Example 4. The results are shown in Table 5 below.
- Tts A U-3500 self-recording spectrophotometer manufactured by Hitachi, Ltd. is used as a measuring instrument, and laminated glass according to JIS R3106 “Testing method for transmittance, reflectance, emissivity, and solar heat gain of plate glass” The Tts of the sample was measured.
- the laminated glass was irradiated with light of 550 W / h for 200 hours using a xenon light resistance tester (manufactured by Toyo Seiki Co., Ltd .: Suntest XLS), and the absorption spectrum of the laminated glass after this light irradiation was measured with a spectrophotometer. The spectrum after the light resistance test was taken.
- the laminated glass whose spectrum before the test was measured in the same manner as described above was heat-treated at a temperature of 100 ° C. for 200 hours with a thermostat (manufactured by Yamato Scientific Co., Ltd .: IG400).
- the absorption spectrum of the heat-treated laminated glass was measured with a spectrophotometer to obtain a spectrum after the heat resistance test.
- the absorbance values in the range of 400 to 900 nm were integrated, and the difference between the values before and after the light resistance / heat resistance test was calculated.
- the laminated glasses of Examples 25 to 36 using the phthalocyanine compound of the present invention are all excellent in heat shielding ability, visible light transmittance, light resistance and heat resistance. The characteristics are shown. In particular, it was very excellent in light resistance and heat resistance.
- the phthalocyanine compound of the present invention has strong absorption in the near-infrared region, very little absorption in the visible light region, good solubility in organic solvents and resins, and very good in light resistance and heat resistance. High durability. Therefore, it is used for applications such as near-infrared cut filters, transparent ink used for security, heat ray shielding films used for automobiles and building windows, interlayer films for laminated glass, infrared thermosensitive recording materials, plastic laser welding, etc. Very useful as a near infrared absorbing dye
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Abstract
Description
特に、プラズマディスプレイなどに用いられる近赤外線カットフィルター、セキュリティ用に用いられる透明インク、あるいは自動車や建物の窓などに用いられる熱線遮蔽材、プラスチックのレーザー溶着などの用途に、近赤外線を吸収する能力が高くかつ可視光線の透過率の高い、すなわち着色が少なく透明度が高い、加えて光や熱に対する耐久性が高く、また有機溶剤や樹脂に溶解する近赤外線吸収材料の開発要求が高まっている。
しかし、シアニン系色素は近赤外線吸収能力が高いものの、耐久性が低く、溶解する有機溶剤も極性溶媒に限定されるという問題がある。ジインモニウム塩系色素は近赤外線吸収能力、耐久性共に低く、溶解する有機溶剤も極性溶媒に限定されるという問題がある。ジチオールニッケル錯体も同様な問題が指摘されており、またその安全性についても問題がある。
本発明に類似したフタロシアニン系化合物(文献5及び6)も提案されているが、可視透過率或いは有機溶剤溶解性、樹脂相溶性に未だ不十分であり、改善が望まれている。
すなわち、本発明は、
(i) 下記一般式(1)で表されるフタロシアニン化合物、
〔式(1)中、Rはアルキル基、アリール基を表し、Xは水素原子、ハロゲン原子、アルキル基を表し、互いに結合して芳香環を形成しても良い。Mは2個の水素原子、2価の金属または3価もしくは4価の金属誘導体を表し、nは3~6の整数を表す。〕
(ii)Rが炭素数1~12の分岐または直鎖アルキル基である(i)のフタロシアニン系化合物。
(iii)Mが2個の水素原子、Pd、Cu、Zn、Pt、Ni、TiO、Co、Fe、Mn、Sn、Al-Cl、VO又はInである、(i)又は(ii)のフタロシアニン系化合物。
(iv)Rがメチル基またはエチル基、Xが水素原子、nが4の整数である(i)~(iii)のフタロシアニン系化合物。
(v)(i)~(iv)のいずれかに記載のフタロシアニン系化合物を含有するする近赤外線吸収材料。
(vi)(i)~(iv)のいずれかに記載のフタロシアニン系化合物を含有する熱線遮蔽材。
(vii)熱線遮蔽フィルムである(vi)の熱線遮蔽材。
(viii)合わせガラス用中間膜である(vii)の熱線遮蔽材。
[フタロシアニン系化合物]
本発明の第1の発明は、一般式(1)で表されるフタロシアニン系化合物である。
〔式(1)中、Rはアルキル基、アリール基を表し、Xは水素原子、ハロゲン原子、アルキル基を表し、互いに結合して芳香環を形成しても良い。Mは2個の水素原子、2価の金属または3価もしくは4価の金属誘導体を表し、nは3~6の整数を表す。〕
アルキル基の例としては、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、イソブチル基、sec-ブチル基、tert-ブチル基、n-ペンチル基、イソペンチル基、ネオペンチル基、tert-ペンチル基、1,2-ジメチルプロピル基、1-メチルブチル基、2-メチルブチル基、n-ヘキシル基、1-メチルペンチル基、2-メチルペンチル基、4-メチルペンチル基、4-メチル-2-ペンチル基、1,2-ジメチルブチル基、2,3-ジメチルブチル基、3,3-ジメチルブチル基、1-エチルブチル基、2-エチルブチル基、n-ヘプチル基、1-メチルヘキシル基、3-メチルヘキシル基、5-メチルヘキシル基、2,4-ジメチルペンチル基、シクロヘキシルメチル基、n-オクチル基、tert-オクチル基、1-メチルヘプチル基、2-エチルヘキシル基、2-プロピルペンチル基、2,5-ジメチルヘキシル基、2,5,5-トリメチルヘキシル基、n-ノニル基、2,2-ジメチルヘプチル基、2,6-ジメチル-4-ヘプチル基、3,5,5-トリメチルヘキシル基、n-デシル基、4-エチルオクチル基、n-ウンデシル基、1-メチルデシル基、n-ドデシル基、1,3,5,7-テトラメチルオクチル基、n-トリデシル基、1-ヘキシルヘプチル基、n-テトラデシル基、n-ペンタデシル基、n-ヘキサデシル基、n-ヘプタデシル基、n-オクタデシル基、n-エイコシル基、n-トリコシル基、n-テトラコシル基、シクロペンチル基、シクロヘキシル基、4-メチルシクロヘキシル基、4-tert-ブチルシクロヘキシル基、シクロヘプチル基、シクロオクチル基などの直鎖、分岐または環状のアルキル基が挙げられる。
また、置換基を有するアルキル基の具体例としては、例えば、メトキシメチル基、エトキシメチル基、n-ブトキシメチル基、n-ヘキシルオキシメチル基、(2-エチルブチルオキシ)メチル基、2-(4'-ペンテニルオキシ)エチル基などの、アルキルオキシ基またはアルケニルオキシ基を有するアルキル基、例えば、ベンジルオキシメチル基、2-(ベンジルオキシメトキシ)エチル基などの、アラルキルオキシ基を有するアルキル基、フェニルオキシメチル基、4-クロロフェニルオキシメチル基、4-(2'-フェニルオキシエトキシ)ブチル基などのアリ-ルオキシ基を有するアルキル基、例えば、n-ブチルチオメチル基、2-n-オクチルチオエチル基などのチオアルキル基を有するアルキル基、例えば、フルオロメチル基、トリフルオロメチル基、パ-フルオロエチル基、4-フルオロシクロヘキシル基、ジクロロメチル基、4-クロロシクロヘキシル基、7-クロロヘプチル基などのハロゲン原子を有するアルキル基が挙げられる。
アリール基の例としてはフェニル基、2-メチルフェニル基、3-メチルフェニル基、4-メチルフェニル基、3-エチルフェニル基、4-エチルフェニル基、4-n-プロピルフェニル基、4-イソプロピルフェニル基、4-n-ブチルフェニル基、4-イソブチルフェニル基、4-tert-ブチルフェニル基、4-n-ペンチルフェニル基、4-イソペンチルフェニル基、4-tert-ペンチルフェニル基、4-n-ヘキシルフェニル基、4-シクロヘキシルフェニル基、4-n-ヘプチルフェニル基、4-n-オクチルフェニル基、4-n-ノニルフェニル基、4-n-デシルフェニル基、4-n-ウンデシルフェニル基、4-n-ドデシルフェニル基、4-n-テトラデシルフェニル基、4-n-ヘキサデシルフェニル基、4-n-オクタデシルフェニル基、2,3-ジメチルフェニル基、2,4-ジメチルフェニル基、2,5-ジメチルフェニル基、2,6-ジメチルフェニル基、3,4-ジメチルフェニル基、3,5-ジメチルフェニル基、3,4,5-トリメチルフェニル基、2,3,5,6-テトラメチルフェニル基、5-インダニル基、
Xがハロゲン原子であるものとしては、塩素原子、フッ素原子、臭素原子、ヨウ素原子が挙げられるが、塩素原子、フッ素原子が好ましく、フッ素原子がより好ましい。
nは4~6が好ましく、特に4が好ましい。
一般式(1)で表されるフタロシアニン系化合物の具体例を下記表1に示すが、これらに限定されるものではない。
特に金属のハロゲン化物又はカルボン酸塩が好ましく用いられ、これらの例としては塩化銅、臭化銅、沃化銅、塩化ニッケル、臭化ニッケル、酢酸ニッケル、塩化コバルト、塩化鉄、塩化亜鉛、臭化亜鉛、沃化亜鉛、酢酸亜鉛、塩化バナジウム、オキシ塩化バナジウム、塩化パラジウム、酢酸パラジウム、塩化アルミニウム、塩化マンガン、塩化鉛、酢酸鉛、塩化インジウム、塩化チタン、塩化スズ等が挙げられる。
金属又は金属誘導体の使用量は、一般式(2)のフタロニトリル系化合物1モル或いは一般式(3)の1,3-ジイミノイソンインドリン系化合物1モルに対し、0.1倍モル~0.6倍モル、好ましくは0.2倍モル~0.5倍モルである。
反応時間は30分~72時間、好ましくは1時間~48時間である。
反応においては、溶媒を使用することが好ましい。反応に使用される溶媒としては沸点60℃以上、好ましくは80℃以上の有機溶媒が好ましい。
例としてメタノール、エタノール、n-プロピルアルコール、n-ブチルアルコール、イソブチルアルコール、n-アミルアルコール、n-ヘキサノール、1-ヘプタノール、1-オクタノール、1-ドデカノール、ベンジルアルコール、エチレングリコール、プロピレングリコール、エトキシエタノール、プロポキシエタノール、ブトキシエタノール、ジメチルエタノール、ジエチルエタノール等のアルコール溶媒、ジクロロベンゼン、トリクロロベンゼン、クロロナフタレン、スルフォラン、ニトロベンゼン、キノリン、DMI(1,3-ジメチル-2-イミダゾリジノン)、尿素等の高沸点溶媒が挙げられる。
溶媒の使用量は一般式(2)のフタロニトリル系化合物或いは一般式(3)の1,3-ジイミノイソンインドリン系化合物の0.5~50倍容量、好ましくは1~15倍容量である。
なお、Mが2個の水素原子であるフタロシアニン化合物の場合は、一般式(2)で表されるフタロニトリル系化合物或いは一般式(3)の1,3-ジイミノイソンインドリン系化合物から選ばれる少なくとも 1 種と金属ナトリウム或いは金属カリウムと上記反応条件にて反応させた後、中心金属であるナトリウム或いはカリウムを塩酸、硫酸等で脱離処理することにより製造できる。
アルキルスルホン酸クロライドとしてメタンスルホン酸クロライド、エタンスルホン酸クロライド、プロパンスルホン酸クロライド、トリフルオロメタンスルホン酸クロライドなどが使用できる。アリールスルホン酸クロライドとしてベンゼンスルホン酸クロライド、トルエンスルホン酸クロライド、クロロベンゼンスルホン酸クロライド、ナフタレンスルホン酸クロライドなどが使用できる。
塩基としては水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、トリエチルアミン、ピリジンなどが使用できる。
塩基の使用量としては一般式(4)のフタロニトリル系化合物1モルに対し、2倍モル~4倍モル、好ましくは2倍モル~3倍モルである。
溶媒の使用量として特に限定するものではないが、フタロニトリル系化合物1モルに対して、500mL~3.0L、好ましくは、1.0~2.0Lである。
反応温度は室温~200℃であり、好ましくは50~150℃、より好ましくは50~100℃である。
反応時間は10分~48時間、好ましくは20分~24時間、より好ましくは30分~12時間である。
Yは塩素、臭素、ヨウ素、フッ素であり、好ましくは塩素、臭素、より好ましくは臭素である。
有機亜鉛試薬の使用量としては一般式(6)のフタロニトリル系化合物1モルに対し、2倍モル~5倍モル、好ましくは2倍モル~3倍モルである。
パラジウム触媒としてビス(トリフェニルホスフィン)パラジウム(II)ジクロリド、ビス(トリ-o-トリルホスフィン)パラジウム(II)ジクロリド、ビス(トリ-o-トリルホスフィン)パラジウム(II)ジクロリド、[1,3-ビス(ジフェニルホスフィノ)プロパン]パラジウム(II)ジクロリドなどが使用できる。
パラジウム触媒の使用量としては一般式(6)のフタロニトリル系化合物1モルに対し、0.01~0.3当量、好ましくは、0.05~0.2当量である。
反応溶媒の使用量としては特に限定するものではないが、一般式(6)のフタロニトリル系化合物1モルに対して、500mL~3.0L、好ましくは、1.0~2.0Lである。
反応温度は室温~200℃であり、好ましくは50~150℃、より好ましくは50~100℃である。
反応時間は10分~48時間、好ましくは20分~24時間、より好ましくは30分~12時間である。
例えば、前記一般式(2)で表されるフタロニトリル系化合物とアンモニアとを、金属アルコキサイドの存在下に反応させることにより製造される。
アンモニアの使用量は一般式(2)のフタロニトリル系化合物1モルに対し、1倍モル~20倍モルであり、好ましくは3倍モル~10倍モルである。
金属アルコキサイドとしては、ナトリウム或いはカリウムのメトキサイド、エトキサイド、n-プロポキサイド、n-ブトキサイド、n-ペントキサイド、n-ヘキシルオキシサイド、n-オクチルオキシサイド、2-メトキシエトキサイド、2-エトキシエトキサイド、2-ブトキシエトキサイド等が用いられる。
金属アルコキサイドの使用量は、一般式(2)のフタロニトリル系化合物に対し、0.01倍モル~5倍モル、好ましくは0.1倍モル~2.0倍モルである。
アルコール系溶媒の使用量は、一般式(2)のフタロニトリル系化合物1モルに対し200mL~15Lであり、好ましくは500mL~5Lである。
反応操作においては、反応溶媒であるアルコール系溶媒に金属ナトリウム又は金属カリウムを添加して金属アルコキサイドのアルコール溶液を調整した後、アンモニア及び一般式(2)のフタロニトリル系化合物を装入して反応しても良く、又他の方法として、アンモニア、一般式(2)のフタロニトリル系化合物及び別途調整した金属アルコキサイドを反応溶媒に装入して反応しても良い。金属アルコキシサイドを調整するために使用する金属の量は、一般式(2)のフタロニトリル系化合物に対し0.01倍モル~5.0倍モル、好ましくは0.1~2.0倍モルである。
反応温度は0℃~溶媒の還流温度であり、好ましくは20℃~溶媒の還流温度である。
反応時間は30分~72時間が好ましい。
反応後、溶媒を留去し、トルエン等の芳香族系溶媒や塩化メチレン等のハロゲン化炭化水素系溶媒にて抽出し、抽出液を水洗、濃縮して析出物をろ過することにより、一般式(3)の1,3-ジイミノベンゾインドリン化合物を得ることができる。
以下に、本発明の近赤外線吸収材料について説明する。
本発明のフタロシアニン系化合物は、熱線を遮蔽する目的の熱線遮蔽材、プラズマディスプレイや液晶ディスプレイ用の光学フィルター、フラッシュ定着トナー、感熱転写・感熱孔版等用の光熱交換剤、レーザー融着用の光熱変換剤、PETボトルの成形加工時のプレヒーティング助剤、半導体レーザーを使う光記録媒体、光学文字読取機等に用いられる近赤外線吸収色素、腫瘍治療用感光性色素、近赤外線吸収フィルターなど、広範囲の用途に用いられる近赤外線吸収材料として非常に有用である。
本発明の近赤外線吸収材料は、前記一般式(1)で表される本発明のフタロシアニン系化合物自体であっても良いし、バインダー樹脂や添加剤など他の成分とともに一般式(1)のフタロシアニン系化合物を含有するものであっても良い。近赤外線吸収材料の態様や成分は、その用途に応じ異なり、多様である。
以下に、本発明の熱線遮蔽材について説明する。
本発明のフタロシアニン系化合物は、建物や自動車の窓等に使用するフィルムや中間膜、ビニールハウス、サンバイザー、溶接用ゴーグルなどに使用される熱線遮蔽材に好適に用いられる。
本発明の熱線遮蔽材は、前記一般式(1)で表される本発明のフタロシアニン系化合物を含有する。本発明の熱線遮蔽材に含有される一般式(1)のフタロシアニン系化合物は、単独の化合物で使用されても良いし、2種以上の混合物の形態であってもよい。
本発明の熱線遮蔽材の使用形態は、特に限定されず、公知のいずれの形態であっても良い。
1.一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する成形体自体を使用する形態
2.基材上に、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する塗膜やフィルム等を適用する形態
3.2枚以上の基材の間に、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有するフィルム等を中間層として設けた積層体の形態
4.基材中に、一般式(1)のフタロシアニン系化合物を含ませた形態
基材としては、特に制限されないが、ガラス板;ポリカーボネート、ポリメチルメタクリレート、ポリスチレン、ポリエチレンテレフタレート、ポリ塩化ビニル、ポリスルフォン、不飽和ポリエステル等の板材等のプラスチック板などが挙げられる。
上記の各形態のうち、特に、2.基材上に、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する塗膜やフィルム等を適用する形態、および3.2枚以上の基材の間に、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有するフィルム等を中間層として設けた積層体の形態、が好ましい。
このように、本発明の熱線遮蔽材は、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する態様が好ましい。
具体的には、ポリカーボネート樹脂;メチルメタクリレート等の(メタ)アクリル樹脂;ポリスチレン、ポリ塩化ビニル、ポリ塩化ビニリデン等のポリビニル樹脂;ポリエチレン、ポリプロピレン等のポリオレフィン樹脂;ポリブチラール樹脂;ポリ酢酸ビニル等の酢酸ビニル系樹脂;ポリエステル樹脂;ポリアミド樹脂;ポリビニルアセタール樹脂;ポリビニルアルコール樹脂;エチレン-酢酸ビニル共重合体樹脂;エチレン-アクリル共重合体樹脂;ポリウレタン樹脂等を挙げることができる。また、実質的に透明であれば、上記1種類の樹脂に限らず、2種以上の樹脂をブレンドしたものも用いることができ、透明性のガラスに上記の樹脂をはさみこんで用いることもできる。
ポリ塩化ビニル樹脂としては、塩化ビニルの単量体のみの重合体ばかりでなく、塩化ビニルを主成分とする共重合体も使用できる。塩化ビニルと共重合させることのできる単量体としては、塩化ビニリデン、エチレン、プロピレン、アクリロニトリル、酢酸ビニル、マレイン酸、イタコン酸、アクリル酸、メタクリル酸等が挙げられる。
本発明の熱線遮蔽材中の、前記一般式(1)で表される本発明のテトラフェニルナフタロシアニン系化合物の含有量は、熱線遮蔽材の厚さにより異なる。
例えば、厚さ3mmの熱線遮蔽板を作製する場合には、熱線遮蔽材に配合される樹脂100重量部に対して、0.002~0.06重量部が好ましく、より好ましくは0.003~0.02重量部である。また、例えば、厚さ10mmの熱線遮蔽板を作製する場合には、樹脂100重量部に対して、0.0005~0.02重量部が好ましく、より好ましくは0.001~0.005重量部である。厚さ10μmの熱線遮蔽フィルムを作製する場合には、樹脂100重量部に対して、0.1~20重量部が好ましく、より好ましくは0.5~10重量部である。熱線遮蔽材の厚さに関係なく一般式(1)のフタロシアニン系化合物の含有量を表示するとすれば、上方からの投影面積中の重量と考えて、0.01~5.0g/m2の配合量が好ましく、より好ましくは0.05~1.0g/m2である。一般式(1)のフタロシアニン系化合物の配合量が、0.01g/m2未満の場合には、熱線遮蔽効果が少なくなり、5.0g/m2を超える場合は可視光線の透過が少なくなる場合がある。
添加剤の熱線遮蔽剤中の添加量は特に制限されるものではないが、通常熱線遮蔽材中10質量%以下である。
特に、本発明の熱線遮蔽材が太陽光に対して用いられるものである場合などには、紫外線吸収剤を含有することは好ましい態様である。紫外線吸収剤としては特に制限されず、公知の紫外線吸収剤が使用できる。具体的には、サリチル酸系、ベンゾフェノン系、ベンゾトリアゾール系、シアノアクリレート系の化合物が好適に使用される。
なお、本発明において、熱線遮蔽材の形状に格別の制約はなく、最も一般的な平板状やフィルム状のほか波板状、球面状、ドーム状など、様々な形状のものが含まれる。
本発明の熱線遮蔽材が平板状やフィルム状の場合、一般式(1)のフタロシアニン系化合物を、樹脂および必要に応じて前記添加剤や他の近赤外線吸収材料と混合後、成形することによって、熱線遮蔽材が得られる。成形方法としては、特に制限されず、公知の成形方法が適用できる。具体的には、押出成形、射出成形、注型重合、プレス成形、カレンダー成形あるいは注型製膜法などが挙げられる。
本発明の熱線遮蔽材の使用形態が、基材上に、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する塗膜を適用する形態である場合、一般式(1)のフタロシアニン系化合物および樹脂と、必要に応じこれらを溶解する溶剤や、その他の成分を含有する塗料(液状ないしペースト状物)を作製し、この塗料を基材に上にコーティングすることにより適用することができる。
本発明の熱線遮蔽材が、建物の窓ガラス等に貼り付けて使用する熱線遮蔽フィルムである場合について以下に説明する。
熱線遮蔽フィルムの構成としては、特に制限はないが、例えば以下のような例が挙げられる。
1.一般式(1)のフタロシアニン系化合物および樹脂を含有するフィルムである態様
2.一般式(1)のフタロシアニン系化合物および樹脂を含有するフィルム、粘着剤層、及び必要に応じて粘着剤層の表面に設けられた剥離シートを有する態様である態様
3.基材上に、一般式(1)のフタロシアニン系化合物および樹脂を含有する層を設けてなる態様
4.基材上に、一般式(1)のフタロシアニン系化合物および粘着剤である樹脂を含有する層、及び必要に応じて粘着剤層の表面に設けられた剥離シートを有する態様
5.基材、一般式(1)のフタロシアニン系化合物および樹脂を含有する層、粘着剤層、及び必要に応じて粘着剤層の表面に設けられた剥離シートを有する態様
上記各態様のうち、窓ガラスへの貼り付け易さ等の点から、粘着剤層を有する態様が好ましく、特に4.または5.の態様が好ましい。
また、これらの態様に加えて、目的に応じて、ハードコート層、防汚層、紫外線吸収層、反射防止層等、更なる層を設けても良い。
粘着剤である樹脂としては、上記の熱可塑性または熱硬化性、活性エネルギー線硬化性の硬化性樹脂粘着剤が挙げられるが、(メタ)アクリル系樹脂が好ましく、ガラス転移温度が0℃未満のポリ(メタ)アクリル酸エステル系樹脂が特に好ましい。
共重合可能な単量体の例としては、ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、メトキシエチル(メタ)アクリレート、エトキシエチル(メタ)アクリレート、エトキシエトキシエチル(メタ)アクリレート等の(メタ)アクリレート類;α-メチルスチレン、ビニルトルエン、スチレンなどに代表されるスチレン系単量体;メチルビニルエーテル、エチルビニルエーテル、イソブチルビニルエーテルなどに代表されるビニルエーテル系単量体;フマル酸、フマル酸のモノアルキルエステル、フマル酸のジアルキルエステル;マレイン酸、マレイン酸のモノアルキルエステル、マレイン酸のジアルキルエステル、イタコン酸、イタコン酸のモノアルキルエステル、イタコン酸のジアルキルエステル、(メタ)アクリロニトリル、塩化ビニル、塩化ビニリデン、酢酸ビニル、ビニルケトン、ビニルピリジン、ビニルカルバゾールなどを挙げることができる。
熱線遮蔽フィルムの各層には、前記熱線遮蔽材を製造する際に用いられる各種の添加剤と同様のものを含有しても良い。例えば、着色剤、重合調節剤、酸化防止剤、光安定剤、紫外線吸収剤、難燃剤、帯電防止剤、可塑剤等が挙げられる。酸化防止剤、難燃剤、接着力調整剤、耐湿剤、蛍光増白剤及び赤外線吸収剤等特に、紫外線吸収剤を含有する態様は好ましい。
また、可視光透過率を大きく低下させない範囲で、カーボンブラック等の熱線を吸収できる材料を併用しても良い。
熱線遮蔽フィルムの厚さは、その構成、基材や熱線遮蔽層の樹脂の種類、その用途などに応じて異なるが、通常、10μm~500μm程度のものが好ましく用いられる。
例えば、熱線遮蔽フィルムが、基材上に、一般式(1)のフタロシアニン系化合物および樹脂を含有する層を設けてなる態様である場合、基材の厚さは20μm~300μm程度が好ましい。また、一般式(1)のフタロシアニン系化合物および樹脂を含有する層の厚さは、0.3~100μm程度が好ましい。
さらに、一般式(1)のフタロシアニン系化合物を含有する樹脂フィルムを作製し、そのフィルムを樹脂材に熱プレスあるいは熱ラミネート成形することにより製造することもできる。また、一般式(1)のフタロシアニン系化合物を含有するアクリル樹脂インクまたは塗料等を樹脂材に印刷またはコーティングすることにより製造することもできる。
本発明の熱線遮蔽材が、自動車の窓ガラス等に使用される合わせガラス用中間膜である場合について以下に説明する。
合わせガラス用中間膜は、2枚のガラスの間に挟んだ形態で用いられる樹脂膜で、本発明の熱線遮蔽材が合わせガラス用中間膜である場合には、一般式(1)のフタロシアニン系化合物および樹脂を必須成分として含有する。
樹脂としては、合わせガラスに用いた際に視認性が十分に確保されるもの、好ましくは合わせガラスとした際の可視光透過率が70%以上のものであれば特に限定されない。
例えば、ポリビニルアセタール系樹脂、ポリ塩化ビニル系樹脂、飽和ポリエステル系樹脂、ポリウレタン系樹脂、エチレン-酢酸ビニル共重合体系樹脂、エチレン-エチルアクリレート共重合体系樹脂等の従来から中間膜用として用いられている熱可塑性樹脂が挙げられる。特に、可塑化されたポリビニルアセタール系樹脂が好ましい。
上記ポリビニルアセタール系樹脂の合成に用いられるPVAは、平均重合度が200~5000のものが好ましく、より好ましくは500~3000のものである。上記ポリビニルアセタール系樹脂は、アセタール化度が40~85モル%であるものが好ましく、より好ましくは50~75モル%のものである。また、残存アセチル基量が30モル% 以下であるものが好ましく、より好ましくは0.5~24モル%のものである。
熱可塑性樹脂、好ましくはポリビニルアセタール系樹脂を可塑化するために用いられる可塑剤としては、例えば、一塩基性有機酸エステル系、多塩基性有機酸エステル系などの有機酸エステル系可塑剤や、有機リン酸系、有機亜リン酸系などのリン酸系可塑剤等が挙げられる。
合わせガラス用中間膜の厚さは、樹脂の種類、その用途などに応じて異なるが、通常、0.1~3mmの範囲内であることが好ましく、0.3mm~1.5mmの範囲内であることがより好ましい。
樹脂に対する一般式(1)のフタロシアニン系化合物の含有量は特に限定されないが、樹脂100重量部に対し一般式(1)のフタロシアニン系化合物を0.001~2重量部の範囲内であることが好ましく、0.005~0.5重量部の範囲内であることがより好ましい。
本発明の合わせガラス用中間膜を製造する方法としては、上記熱線遮蔽材、熱線遮蔽フィルムを製造する際と同様の方法が挙げられる。
本発明の合わせガラス用中間膜は、必要に応じて、プライマー機能、紫外線カット機能、難燃機能、反射防止機能、防眩機能、反射防止防眩機能、帯電防止機能のいずれか一つ以上の機能を有する機能性透明層とあわせた複層構造としても良い。
本発明の合わせガラス用中間膜を使用した合わせガラスは、少なくとも二枚の透明ガラス基材の間に本発明の中間膜が挟持され接着一体化された構成となる。
合わせガラスの作製方法としては、例えば、二枚の透明ガラス基材の間に本発明の中間膜を挟んで真空バッグの中に入れ、この真空バッグ内の圧力が約-65~-100kPaの減圧度となるように減圧吸引しながら温度約70~110℃で予備接着を行った後、さらに、オートクレーブ中で、オートクレーブ内の圧力が約0.98~1.47MPaの減圧度となるように減圧吸引しながら温度約120~150℃で本接着を行うことにより、得ることができる。
るものではない。
[実施例1] フタロシアニン系化合物(具体例(1)-30)の製造
4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6g、三塩化バナジウム4.76g、DBU13.74gを1-ペンタノール100mL中、内温125℃にて24時間撹拌した。メタノール600mLを添加、析出物をろ取、乾燥した。カラムクロマトグラフィー(シリカゲル/トルエン)で精製して深緑色粉末14.5gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 1267M+)
・元素分析値:実測値(C:68.20%、H:7.66%、N:8.82%);
理論値(C:68.17%、H:7.63%、N:8.83%)
このようにして得られた化合物のトルエン溶液は734.0nmに極大吸収を示し、グラム吸光係数は1.21×105mL/g・cmであった。この吸収スペクトルチャートを図1に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-エトキシブチル)-1,3-ジイミノベンゾイソインドリン20.3gを使用した以外は実施例1と同様にして深緑色粉末14.8gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 1379M+)
・元素分析値:実測値(C:69.57%、H:8.15%、N:8.08%)
理論値(C:69.59%、H:8.18%、N:8.12%)
このようにして得られた化合物のトルエン溶液は734.0nmに極大吸収を示し、グラム吸光係数は1.19×105mL/g・cmであった。この吸収スペクトルチャートを図2に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-フェノキシブチル)-1,3-ジイミノベンゾイソインドリン25.9gを使用した以外は実施例1と同様にして深緑色粉末17.7gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 1764M+)
・元素分析値:実測値(C:76.24%、H:6.42%、N:6.36%)
理論値(C:76.21%、H:6.40%、N:6.35%)
このようにして得られた化合物のトルエン溶液は735.5nmに極大吸収を示し、グラム吸光係数は8.63×104mL/g・cmであった。この吸収スペクトルチャートを図3に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-(3-メトキシフェノキシ)ブチル)-1,3-ジイミノベンゾイソインドリン29.4gを使用した以外は実施例1と同様にして深緑色粉末5.9gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2003M+)
・元素分析値:実測値(C:71.85%、H:6.44%、N:5.57%)
理論値(C:71.87%、H:6.43%、N:5.59%)
このようにして得られた化合物のトルエン溶液は735.5nmに極大吸収を示し、グラム吸光係数は7.40×104mL/g・cmであった。この吸収スペクトルチャートを図4に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-(4-(tert―ブチル)フェノキシ)ブチル)-1,3-ジイミノベンゾイソインドリン32.5gを使用した以外は実施例1と同様にして深緑色粉末13.0gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2213M+)
・元素分析値:実測値(C:78.15%、H:8.02%、N:5.08%)
理論値(C:78.12%、H:8.01%、N:5.06%)
このようにして得られた化合物のトルエン溶液は734.5nmに極大吸収を示し、グラム吸光係数は7.10×104mL/g・cmであった。この吸収スペクトルチャートを図5に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-(2-フルオロフェノキシ)ブチル)-1,3-ジイミノベンゾイソインドリン28.0gを使用した以外は実施例1と同様にして深緑色粉末11.2gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 1908M+)
・元素分析値:実測値(C:70.49%、H:5.51%、N:5.85%)
理論値(C:70.47%、H:5.49%、N:5.87%)
このようにして得られた化合物のトルエン溶液は735.5nmに極大吸収を示し、グラム吸光係数は7.89×104mL/g・cmであった。この吸収スペクトルチャートを図6に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-(2,6-ジメトキシフェノキシ)ブチル)-1,3-ジイミノベンゾイソインドリン32.9gを使用した以外は実施例1と同様にして深緑色粉末19.7gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2245M+)
・元素分析値:実測値(C:68.44%、H:6.44%、N:4.99%)
理論値(C:68.47%、H:6.46%、N:4.99%)
このようにして得られた化合物のトルエン溶液は734.5nmに極大吸収を示し、グラム吸光係数は6.75×104mL/g・cmであった。この吸収スペクトルチャートを図7に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-(2-フェノキシエトキシ)ブチル)-1,3-ジイミノベンゾイソインドリン31.0gを使用した以外は実施例1と同様にして深緑色粉末14.9gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2117M+)
・元素分析値:実測値(C:72.62%、H:6.86%、N:5.27%)
理論値(C:72.60%、H:6.85%、N:5.29%)
このようにして得られた化合物のトルエン溶液は735.0nmに極大吸収を示し、グラム吸光係数は7.16×104mL/g・cmであった。この吸収スペクトルチャートを図8に示す。
実施例1における三塩化バナジウム4.76gの代わりに塩化第一銅3.00gを使用した以外は実施例1と同様にして深緑色粉末14.9gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 1264M+)
・元素分析値:実測値(C:76.36%、H:6.40%、N:6.34%)
理論値(C:76.36%、H:6.41%、N:6.36%)
このようにして得られた化合物のトルエン溶液は705.5nmに極大吸収を示し、グラム吸光係数は7.89×104mL/g・cmであった。この吸収スペクトルチャートを図9に示す。
実施例4における三塩化バナジウム4.76gの代わりに塩化第一銅3.00gを使用した以外は実施例1と同様にして深緑色粉末13.5gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2001M+)
・元素分析値:実測値(C:72.01%、H:6.45%、N:5.61%)
理論値(C:72.00%、H:6.44%、N:5.60%)
このようにして得られた化合物のトルエン溶液は706.5nmに極大吸収を示し、グラム吸光係数は6.78×104mL/g・cmであった。この吸収スペクトルチャートを図10に示す。
[実施例11] フタロシアニン系化合物(具体例(1)-45)の製造
実施例7における三塩化バナジウム4.76gの代わりに塩化第一銅3.00gを使用した以外は実施例1と同様にして深緑色粉末12.1gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2241M+)
・元素分析値:実測値(C:68.59%、H:6.44%、N:5.03%)
理論値(C:68.57%、H:6.47%、N:5.00%)
このようにして得られた化合物のトルエン溶液は706.5nmに極大吸収を示し、グラム吸光係数は6.01×104mL/g・cmであった。この吸収スペクトルチャートを図11に示す。
[実施例12] フタロシアニン系化合物(具体例(1)-32)の製造
実施例1における三塩化バナジウム4.76gの代わりに塩化亜鉛4.12gを使用した以外は実施例1と同様にして深緑色粉末7.4gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 2003M+)
・元素分析値:実測値(C:71.95%、H:6.47%、N:5.61%)
理論値(C:71.93%、H:6.44%、N:5.59%)
このようにして得られた化合物のトルエン溶液は705.0nmに極大吸収を示し、グラム吸光係数は7.23×104mL/g・cmであった。この吸収スペクトルチャートを図12に示す。
実施例1における4,7-ビス(4-メトキシブチル)-1,3-ジイミノベンゾイソインドリン18.6gの代わりに4,7-ビス(4-メトキシメチル)-1,3-ジイミノベンゾイソインドリン13.7gを使用した以外は実施例1と同様にして深緑色粉末9.3gを得た。得られた化合物は、下記の分析結果より目的の化合物であることを確認した。
・MS:(EI)m/z 931M+)
・元素分析値:実測値(C:61.85%、H:5.16%、N:11.99%)
理論値(C:61.87%、H:5.19%、N:12.02%)
このようにして得られた化合物のトルエン溶液は733.0nmに極大吸収を示し、グラム吸光係数は1.30×105mL/g・cmであった。この吸収スペクトルチャートを図13に示す。
・MS:(EI)m/z 1716M+)
・元素分析値:実測値(C:72.70%、H:9.35%、N:6.55%)
理論値(C:72.73%、H:9.39%、N:6.52%)
このようにして得られた化合物のトルエン溶液は737.5nmに極大吸収を示し、グラム吸光係数は1.05×105mL/g・cmであった。この吸収スペクトルチャートを図14に示す。
上記実施例で製造した本発明のフタロシアニン化合物は芳香族有機溶媒(例えば、ベンゼン、トルエン、キシレン、メシチレン等)に対する溶解度が高い。また極性有機溶媒(アセトン、酢酸エチル、炭酸プロピレン、シクロペンタノン等)に対する溶解度も高い。シクロペンタノンに対する溶解度を下記方法で測定した。結果を表2に示す。
(溶解度測定法)
フタロシアニン化合物約1gに、総重量が約10gになるようにシクロペンタノンを加え、超音波を約30分照射し、その後室温で二時間撹拌して、約10wt%の分散液を調製した。
この分散液をメンブランフィルタ(0.2μm)で濾過し、得られた濾物を60℃の乾燥器で1時間乾燥後、濾物の重量を測定した。
フタロシアニン化合物の溶剤に対する溶解度を、以下の式で表した。
溶解度(wt%)=(W0-W1)/W0
なお、W0:処理前のフタロシアニン化合物の正確な重量、W1:乾燥後の濾物(フタロシアニン化合物の溶解残分)の重量である。フィルタに濾物が残余しなかった場合は、溶解度は 10wt%以上とした。
実施例の化合物はいずれも比較例の化合物と比較してシクロペンタノンに対する溶解性が高い。
本発明のフタロシアニン系化合物及び比較例化合物の可視光透過率を、下記測定法により測定した。結果を表3に示す。
また、実施例1・実施例3で製造した本発明のフタロシアニン系化合物および比較例1・比較例2の化合物の透過スペクトルの比較を図15に示す。
(可視光透過率測定法)
100mLメスフラスコに、各フタロシアニン系化合物1.000mgと約90mLのクロロホルムを入れ、超音波を30分間照射した後、室温で2時間静置した。その後、溶液のメニスカスがメスフラスコの標線と一致するようにクロロホルムを添加して10mg/Lのフタロシアニン溶液を調製した。このように調製した溶液を1cm角のパイレックス(登録商標)製セルに入れ、分光光度計(日立製作所社製:Spectrophotometer U-3500)を用いて吸収スペクトルを測定した。
このようにして測定した吸収スペクトルより、近赤外領域の吸収極大波長における吸光度が1.0、すなわち透過率が10%となるように換算をおこない透過スペクトルを得た。この透過スペクトルの460nmおよび610nmにおける透過率を表3に示す。比較例 1・2と比較して本発明の化合物は460nmにおける透過率はほぼ同等であるが、610nmにおける透過率は向上した。
実施例1で製造したフタロシアニン系化合物(具体例(1)-30)5g、アクリル樹脂LP-45M(製品名、綜研化学株式会社製)50g、メチルエチルケトン20g、トルエン20gを混合撹拌して、樹脂組成物を製造した。
透明基材としての厚さ100μmのポリエチレンテレフタレートフィルム(PETフィルム)に、上記樹脂組成物を厚さ2.5μmとなるようにバー塗布し、その後100℃で3分間乾燥した。さらに、PETフィルムの他方の面(樹脂組成物を塗布していない面)に、透明なアクリル共重合系の粘着剤を厚さが20μmとなるようバー塗布し、100℃で3分間乾燥硬化させた後、粘着剤面に剥離フィルムを貼着し、熱線遮蔽フィルムを製造した。
[実施例14] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-33の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-37の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例16] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-39の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-42の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例18] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-43の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例19] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-44の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-38の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例21] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-31の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例22] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-40の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-45の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
[実施例24] 熱線遮蔽フィルムの製造
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに具体例(1)-32の化合物を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
実施例13において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに比較例1の化合物(a)を使用した以外は実施例13と同様に操作を行って、熱線遮蔽フィルムを製造した。
上記実施例13~24及び比較例3で製造した熱線遮蔽フィルムについて、以下の項目を評価した。結果を下記の表4に示す。
なお、評価試験においては、製造した熱線遮蔽フィルムの剥離フィルムを剥がし、5cm×5cm×3mm厚のガラス板に圧着させて試験片を作成し、これを用いた。
測定機器として(株)日立製作所製、U-3500型自記分光光度計を使用し、JIS R3106「板ガラス類の透過率・反射率・放射率・日射熱取得率の試験方法」に準じ、合わせガラスサンプルのTtsを測定した。
なお、Tts(Total solar energy transmitted through a glazing)は、全日射透過率を表し、値が小さいほど熱遮蔽能力が高いことを示す。
耐光性試験は、試験片の吸収スペクトルを分光光度計(日立製作所(株)社製:Spectrophotometer U-3500で測定し、これを耐光性試験前スペクトルとした。次に、試験前スペクトルを測定した試験片をキセノン耐光性試験機(東洋精機社製:サンテストXLS+)を用い550W/hの光を200時間照射した。光照射した試験片の吸収スペクトルを分光光度計にて測定し、耐光性試験後スペクトルとした。
耐熱性試験は、上記と同様にして試験前スペクトルを測定した試験片を、恒温器(ヤマト科学社製:IG400)で温度100℃にて200時間加熱処理した。この加熱処理した試験片の吸収スペクトルを分光光度計にて測定し、耐熱性試験後のスペクトルとした。
このようにして測定した耐光・耐熱性試験前後の各スペクトルにおいて、400~900nmの範囲の吸光度値を積分し、耐光・耐熱試験前後でその値の差を算出した。
耐光・耐熱試験前後での吸光度の差ΔEを、下記の式で表した。
ΔΕ(%)={Σ(E1の400~900nm)-Σ(E2の400~
900nm)}/Σ(E1の400~900nm)×100
なお、E1:試験前スペクトル、E2:試験後スペクトル、Σ:吸光度値の積分である。
ΔΕの値が大きいほど、耐光・耐熱試験前後でのスペクトル変化が大きい。
表8に示されるように、比較例に比べて実施例の熱線遮蔽フィルムはいずれも熱遮蔽能力、耐光性ならびに耐熱性において優れた特性を示した。特に、耐光性、耐熱性において非常に優れていた。
<合わせガラス用中間膜の作製>
有機エステル可塑剤として、トリエチレングリコール-ジ-2-エチルヘキサノエート40gに、実施例1で製造したフタロシアニン系化合物(具体例(1)-30)0.013gを溶解させ、この溶液を、ポリビニルブチラール樹脂(商品名:BH-3、積水化学工業社製)100gに添加し、ミキシングロールで充分に溶融混練した後、押出機を用いて押出して、厚み0.76mmの中間膜を得た。
上記中間膜を、100mm×100mmのサイズに切断し、JIS R3208 に準拠した熱線吸収板ガラス(縦100mm×横100mm×厚さ2.0mm)で挟み込み、ゴムバック内に入れ、2.6kPaの真空度で20分間脱気した後、脱気したままオーブン内に移し、更に90℃で30分間保持して真空プレスした。その後、オートクレーブにて温度130℃、圧力1.3MPaの条件で20分間圧着し、合わせガラスのサンプルを得た。
実施例25において、フタロシアニン系化合物を実施例2で製造した化合物(具体例(1)-33)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例27]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例3で製造した化合物(具体例(1)-37)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例28]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例4で製造した化合物(具体例(1)-39)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例29]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例5で製造した化合物(具体例(1)-42)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
実施例25において、フタロシアニン系化合物を実施例6で製造した化合物(具体例(1)-43)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例31]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例7で製造した化合物(具体例(1)-44)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例32]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例8で製造した化合物(具体例(1)-38)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例33]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例9で製造した化合物(具体例(1)-31)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
実施例25において、フタロシアニン系化合物を実施例10で製造した化合物(具体例(1)-40)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例35]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例11で製造した化合物(具体例(1)-45)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
[実施例36]合わせガラス用中間膜及び合わせガラスの作製
実施例25において、フタロシアニン系化合物を実施例12で製造した化合物(具体例(1)-32)に変更した以外は同様に操作を行って合わせガラス用中間膜及び合わせガラスを作製した。
実施例25において、フタロシアニン系化合物として具体例(1)-30の化合物の代わりに比較例1化合物(a)を使用した以外は実施例25と同様に操作を行って、合わせガラス用中間膜及び合わせガラスを作製した。
上記実施例25~36及び比較例4で作製した合わせガラスのサンプルについて、以下の項目を評価した。結果を下記の表5に示す。
[Tts]
測定機器として(株)日立製作所製、U-3500型自記分光光度計を使用し、JIS R3106「板ガラス類の透過率・反射率・放射率・日射熱取得率の試験方法」に準じ、合わせガラスサンプルのTtsを測定した。
測定機器として(株)日立製作所製、U-3500型自記分光光度計を使用し、JIS R 3212「自動車用安全ガラス試験方法」に準じ、合わせガラスサンプルの波長380~780nmにおける可視光線透過率を測定した。
[耐光・耐熱性]
耐光性試験は、合わせガラスの吸収スペクトルを分光光度計(日立製作所(株)社製:Spectrophotometer U-3500で測定し、これを耐光性試験前スペクトルとした。次に、試験前スペクトルを測定した合わせガラスをキセノン耐光性試験機(東洋精機社製:サンテストXLS+)を用い550W/hの光を200時間照射した。この光照射した後の合わせガラスの吸収スペクトルを分光光度計にて測定し、耐光性試験後スペクトルとした。
耐熱性試験は、上記と同様にして試験前スペクトルを測定した合わせガラスを、恒温器(ヤマト科学社製:IG400)で温度100℃にて200時間加熱処理した。この加熱処理した合わせガラスの吸収スペクトルを分光光度計にて測定し、耐熱性試験後のスペクトルとした。
このようにして測定した耐光・耐熱性試験前後の各スペクトルにおいて、400~900nmの範囲の吸光度値を積分し、耐光・耐熱性試験前後でその値の差を算出した。
耐光・耐熱性試験前後での吸光度の差ΔEを、下記の式で表した。
ΔΕ(%)={Σ(E1の400~900nm)-Σ(E2の400~
900nm)}/Σ(E1の400~900nm)×100
なお、E1:試験前スペクトル、E2:試験後スペクトル、Σ:吸光度値の積分である。 ΔΕの値が大きいほど、耐光・耐熱試験前後でのスペクトル変化が大きい。
表5に示されるように、比較例4に比べて本願発明のフタロシアニン化合物を用いた実施例25~36の合わせガラスは、いずれも熱遮蔽能力、可視光線透過率、耐光性ならびに耐熱性において優れた特性を示した。特に、耐光性、耐熱性において非常に優れていた。
そのため、近赤外線カットフィルター、セキュリティ用に用いられる透明インク、自動車や建物の窓などに用いられる熱線遮蔽フィルム、合わせガラス用中間膜、赤外線感熱記録材料、プラスチックのレーザー熔着などの用途に用いられる近赤外線吸収色素として非常に有用である
Claims (8)
- Rが炭素数1~12の分岐または直鎖アルキル基である請求項1のフタロシアニン系化合物。
- Mが2個の水素原子、Pd、Cu、Zn、Pt、Ni、TiO、
Co、Fe、Mn、Sn、Al-Cl、VO又はInである、請求項1または2のフタロシアニン系化合物。 - Rがメチル基またはエチル基、Xが水素原子、nが4である請求項1~3のいずれかに記載のフタロシアニン系化合物。
- 請求項1~4のいずれかに記載のフタロシアニン系化合物の少なくとも1種を含有する近赤外線吸収材料。
- 請求項1~4のいずれかに記載のフタロシアニン系化合物の少なくとも1種を含有する熱線遮蔽材。
- 熱線遮蔽フィルムである、請求項6の熱線遮蔽材。
- 合わせガラス用中間膜である、請求項6の熱線遮蔽材。
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CN201880023510.7A CN110494501B (zh) | 2017-04-07 | 2018-04-06 | 酞菁系化合物、及其用途 |
KR1020197032577A KR20190133760A (ko) | 2017-04-07 | 2018-04-06 | 프탈로시아닌계 화합물 및 그의 용도 |
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KR20180113914A (ko) * | 2017-04-07 | 2018-10-17 | 제이에스알 가부시끼가이샤 | 고체 촬상 소자용 조성물, 적외선 차폐막 및 고체 촬상 소자 |
WO2020071470A1 (ja) * | 2018-10-05 | 2020-04-09 | 山本化成株式会社 | フタロシアニン系化合物、及びその用途 |
WO2020071486A1 (ja) * | 2018-10-05 | 2020-04-09 | Jsr株式会社 | 光学センサー用組成物 |
JP2021047216A (ja) * | 2019-09-17 | 2021-03-25 | Jsr株式会社 | 硬化性組成物 |
WO2022138925A1 (ja) * | 2020-12-25 | 2022-06-30 | 富士フイルム株式会社 | 波長選択吸収フィルタ及び表示装置 |
JP7463677B2 (ja) | 2019-09-17 | 2024-04-09 | Toppanホールディングス株式会社 | 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、固体撮像素子用フィルターの製造方法 |
JP7463678B2 (ja) | 2019-09-17 | 2024-04-09 | Toppanホールディングス株式会社 | 赤外光カットフィルター、固体撮像素子用フィルター、固体撮像素子、および、固体撮像素子用フィルターの製造方法 |
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JP7128804B2 (ja) * | 2017-04-07 | 2022-08-31 | 山本化成株式会社 | ナフタロシアニン化合物、その製造方法および用途 |
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CN110494501A (zh) | 2019-11-22 |
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CN110494501B (zh) | 2022-04-19 |
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US20200032066A1 (en) | 2020-01-30 |
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