JP2012507595A - フッ素化ビス(フタロシアニルアルミノキシ)シリル顔料 - Google Patents
フッ素化ビス(フタロシアニルアルミノキシ)シリル顔料 Download PDFInfo
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- JP2012507595A JP2012507595A JP2011534503A JP2011534503A JP2012507595A JP 2012507595 A JP2012507595 A JP 2012507595A JP 2011534503 A JP2011534503 A JP 2011534503A JP 2011534503 A JP2011534503 A JP 2011534503A JP 2012507595 A JP2012507595 A JP 2012507595A
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- 239000000049 pigment Substances 0.000 title claims description 80
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
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- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 125000005647 linker group Chemical group 0.000 claims abstract description 3
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- 239000002270 dispersing agent Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
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- 125000000524 functional group Chemical group 0.000 claims description 2
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- 239000012736 aqueous medium Substances 0.000 claims 2
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
- PTUUTGJMRQWABQ-UHFFFAOYSA-N triphenyl(phenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[SiH2]C1=CC=CC=C1 PTUUTGJMRQWABQ-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
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- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 3
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 3
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- 239000004743 Polypropylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- RQALCWOAACVOPZ-UHFFFAOYSA-N [2,5-dichloro-4-[hydroxy(dimethyl)silyl]phenyl]-hydroxy-dimethylsilane Chemical compound C[Si](C)(O)C1=CC(Cl)=C([Si](C)(C)O)C=C1Cl RQALCWOAACVOPZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- 238000001636 atomic emission spectroscopy Methods 0.000 description 1
- OCVSBJXTWPHUPQ-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(=O)OCC1=CC=CC=C1 OCVSBJXTWPHUPQ-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- CODLZAHLCIPWQM-UHFFFAOYSA-N bis[hydroxy(diphenyl)silyl]-dimethylsilane Chemical compound C=1C=CC=CC=1[Si](O)(C=1C=CC=CC=1)[Si](C)(C)[Si](O)(C=1C=CC=CC=1)C1=CC=CC=C1 CODLZAHLCIPWQM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- MCNRYZZFTMGVQN-UHFFFAOYSA-N cyclohexyl-(cyclohexyl-hydroxy-methylsilyl)oxy-hydroxy-methylsilane Chemical compound C1CCCCC1[Si](O)(C)O[Si](C)(O)C1CCCCC1 MCNRYZZFTMGVQN-UHFFFAOYSA-N 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- HKGQTXCGPDIVTR-UHFFFAOYSA-N ethenyl-(ethenyl-hydroxy-methylsilyl)oxy-hydroxy-methylsilane Chemical compound C=C[Si](O)(C)O[Si](C)(O)C=C HKGQTXCGPDIVTR-UHFFFAOYSA-N 0.000 description 1
- NKHCRHZSTOJEBA-UHFFFAOYSA-N ethenyl-[4-(ethenyl-hydroxy-methylsilyl)phenyl]-hydroxy-methylsilane Chemical compound C=C[Si](O)(C)C1=CC=C([Si](C)(O)C=C)C=C1 NKHCRHZSTOJEBA-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- LWIGVRDDANOFTD-UHFFFAOYSA-N hydroxy(dimethyl)silane Chemical compound C[SiH](C)O LWIGVRDDANOFTD-UHFFFAOYSA-N 0.000 description 1
- ZQXDVTXVCSPBQF-UHFFFAOYSA-N hydroxy-(hydroxy-methyl-pent-1-ynylsilyl)oxy-methyl-pent-1-ynylsilane Chemical compound CCCC#C[Si](C)(O)O[Si](C)(O)C#CCCC ZQXDVTXVCSPBQF-UHFFFAOYSA-N 0.000 description 1
- UVHIGFFQUKEROC-UHFFFAOYSA-N hydroxy-[2-[hydroxy(dimethyl)silyl]ethyl]-dimethylsilane Chemical compound C[Si](C)(O)CC[Si](C)(C)O UVHIGFFQUKEROC-UHFFFAOYSA-N 0.000 description 1
- XJGQIGUINNBSDH-UHFFFAOYSA-N hydroxy-[2-[hydroxy(dimethyl)silyl]ethynyl]-dimethylsilane Chemical compound C[Si](C)(O)C#C[Si](C)(C)O XJGQIGUINNBSDH-UHFFFAOYSA-N 0.000 description 1
- JVAGHSUZSKGBTB-UHFFFAOYSA-N hydroxy-[3-[hydroxy(dimethyl)silyl]-1-adamantyl]-dimethylsilane Chemical compound C1C(C2)CC3CC1([Si](C)(O)C)CC2([Si](C)(C)O)C3 JVAGHSUZSKGBTB-UHFFFAOYSA-N 0.000 description 1
- VZSUUFCWNGDTIE-UHFFFAOYSA-N hydroxy-[4-[4-[hydroxy(dimethyl)silyl]phenoxy]phenyl]-dimethylsilane Chemical compound C1=CC([Si](C)(O)C)=CC=C1OC1=CC=C([Si](C)(C)O)C=C1 VZSUUFCWNGDTIE-UHFFFAOYSA-N 0.000 description 1
- UGDKZFAENAFPAM-UHFFFAOYSA-N hydroxy-[4-[hydroxy(dimethyl)silyl]-2,3,5,6-tetramethylphenyl]-dimethylsilane Chemical compound CC1=C(C)C([Si](C)(C)O)=C(C)C(C)=C1[Si](C)(C)O UGDKZFAENAFPAM-UHFFFAOYSA-N 0.000 description 1
- YJNJBVBQJBKHFB-UHFFFAOYSA-N hydroxy-[[[hydroxy-methyl-(3,3,3-trifluoropropyl)silyl]oxy-methyl-(3,3,3-trifluoropropyl)silyl]oxy-methyl-(3,3,3-trifluoropropyl)silyl]oxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](O)(C)O[Si](C)(CCC(F)(F)F)O[Si](C)(CCC(F)(F)F)O[Si](C)(O)CCC(F)(F)F YJNJBVBQJBKHFB-UHFFFAOYSA-N 0.000 description 1
- MYZTUAOLAYIKSJ-UHFFFAOYSA-N hydroxy-[hydroxy(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)O[Si](O)(C=1C=CC=CC=1)C1=CC=CC=C1 MYZTUAOLAYIKSJ-UHFFFAOYSA-N 0.000 description 1
- YIEYFTCHMWPYGB-UHFFFAOYSA-N hydroxy-[hydroxy-bis(3-methylphenyl)silyl]oxy-bis(3-methylphenyl)silane Chemical compound CC1=CC=CC([Si](O)(O[Si](O)(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 YIEYFTCHMWPYGB-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N iso-butyl alcohol Natural products CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000178 monomer Substances 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 238000010951 particle size reduction Methods 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 239000002745 poly(ortho ester) Substances 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000012798 spherical particle Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
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- 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
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
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- 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
- C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
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- 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
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
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- C09B69/00—Dyes not provided for by a single group of this subclass
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- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/008—Dyes containing a substituent, which contains a silicium atom
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Abstract
Description
R1及びR2は独立して、置換若しくは非置換の炭素原子数8以下のアルキル基、アルケニル基、アルキニル基若しくはシクロアルキル基、又は炭素原子数10以下のアリール基であり、
R3は、酸素、R1R2Si、置換又は非置換のアルキル基、アルケニル基、アルキニル基、シクロアルキル基又はアリール基を含む二価の連結基(divalent linking group)であり、
R1、R2及びR3は環の構成要素を含んでいてもよく、
nは1〜4であり、
zは1〜4である)
に従うフタロシアニル基の各々に直接結合したフッ素化ビス(フタロシアニルアルミノ)シロキシル顔料を提供する。
クロロアルミニウムテトラフルオロフタロシアニンの調製:
100mL容の三つ口丸底フラスコに、マグネチックスターラーバー、20gの1−クロロナフタレン、0.12g(2mmol)の尿素、9.13g(62.5mmol)の4−フルオロフタロニトリル、次いで2.0g(15mmol)の三塩化アルミニウムを入れ、最後に20gの1−クロロナフタレンを用いて漏斗を洗いこんだ。フラスコに温度計及び窒素注入口付き冷却器を取り付けた。反応を連続的に磁気攪拌しながらマントルヒーターによって加熱した。反応混合物は徐々に暗色化していき、約210℃でブルーグリーンの色が幾らか見られた。210℃の温度で反応は発熱し始め、約255℃で急速に加熱還流すると同時に濃い青色(deep blue)に発色した。反応を3時間255℃に保った。その後、濃い暗藍色(blue black)の固体が形成されるが、反応液は茶色がかっており、抵抗なく(freely)撹拌された。反応を100℃まで冷却した後、60mLのキシレンを添加し、反応を20分間撹拌した。混合物を温かいうちにブフナー漏斗でワットマン54番濾紙を通して濾過し、暗藍色の沈殿物を回収した。この沈殿物を50mLのキシレン、続いて100mLのアセトンで洗った。濾液は初めは茶色がかっているが、徐々に薄い青色に変化した。回収した固体を250mL容の三角(erlenmyer)フラスコに入れ、50mLの5%NaOH水溶液を添加し、混合物を20分間激しく磁気撹拌した。不溶性物質をブフナー漏斗上で回収した。回収した生成物を50mLのアセトン、続いて50mLのリグロインで洗った後、ブフナー漏斗上で乾燥させた。生成物を250mL容の三角フラスコに戻し、50mLの5%NH4OH水溶液を添加した。この固体は完全に乾燥している(non wetting)。すなわち、固体は無色の液体の上部に完全に乾燥した粉末としてとどまり、撹拌しても固体が湿ることはない。この乾燥粉末をブフナー漏斗上で回収した。濾液は完全に無色であった。回収した固体を50mLの蒸留水、100mLのアセトンで洗った後、20分間ブフナー漏斗上で乾燥させた。250mL容の三角フラスコに移した後、100mLのアセトンを添加した。混合物をホットプレート上で撹拌しながら沸騰させて、15分間沸騰を保った後、熱いうちにワットマン54番濾紙を通して濾過した。濾液は非常に薄い青色である。生成物を15分間ブフナー漏斗上で乾燥させた後、60℃の真空オーブン内で一晩乾燥させた。濃い紺青色(dark blue)の粉末である回収された中間体クロロアルミニウムテトラフルオロフタロシアニンの重量は9.3gであった(14.3mmol、収率95.9%)。融点:310℃超。
100mL容の一口丸底フラスコに、5.4g(8.3mmol)のクロロアルミニウムテトラフルオロフタロシアニン、35mLのピリジン及び1.9g(8.5mmol)のジフェニルシランジオールをこの順序で入れた。フラスコにマグネチックスターラーバーを入れ、冷却器及び窒素注入口を取り付けた。フラスコを130℃に予熱した油浴内に入れた。反応を撹拌し、一晩加熱還流させた。クロロアルミニウムテトラフルオロフタロシアニンは熱ピリジン中に部分的に溶解したようであった。反応液は一晩撹拌した後でも濃い青色のままであり、抵抗なく撹拌された。フラスコを油浴から取り出し、約100℃まで冷却し、不溶性生成物をブフナー漏斗でワットマン54番濾紙を用いて回収した(熱いうちに濾過を行った)。回収した青色の生成物を、洗液(washes)が非常に薄い青色となるまで4×50mLのピリジンで洗った後、100mLのアセトン及び25mLのリグロインP950で洗った。生成物を1時間ブフナー漏斗上で乾燥させた後、60℃の真空オーブン内で1時間乾燥させた。濃い青色の生成物の重量は6.4gであった(3.9mmol、理論値の(of theory)94.3%)。IR及びMSによる分析から、少量の出発物質が依然としてこの単離生成物中に含まれることが示される。この粗生成物を250mL容の三角フラスコに入れ、還流下で40分間、125mLのジメチルホルムアミドでスラリー状にした。不溶性物質をブフナー漏斗でワットマン54番濾紙を用いて回収した。この熱DMFスラリー精製を再度繰り返した。最終生成物をブフナー漏斗上で回収し、50mLのアセトン及び25mLのリグロインP950で洗った後、110℃の真空オーブン内で一晩乾燥させた。濃い青色の粉末である回収されたInv−1の重量は4.9gであった(2.99mmol、理論値の72.2%)。最終生成物をGC質量分析によって分析したところ、2.2%のDMFが検出された(錯体1mol当たり0.5molのDMF)。
250mL容の一口丸底フラスコに、70mLのピリジン、10mLの蒸留水、8.4g(13mmol)のクロロアルミニウムテトラフルオロフタロシアニン及び3.54g(14mmol)のジクロロジフェニルシランをこの順序で入れた。混合物を磁気撹拌した。フラスコに還流冷却器及び窒素注入口を取り付けた後、還流下で5時間、油浴内で加熱した。ジクロロジフェニルシランの添加によって強く発熱した。反応液は容易に撹拌され、緑がかった青色の色合いを呈していた。還流下で5時間後、フラスコを油浴から取り出し、室温で30分間撹拌して冷却した。濃い青色の不溶性生成物をブフナー漏斗でワットマン54番濾紙を用いて回収し、2×25mLの蒸留水で洗った。この濃い青色の生成物を500mL容の三角フラスコに移し、200mLのアセトンを添加した。混合物を撹拌し、加熱還流した。還流下で30分間保った後、混合物を室温まで冷却し、不溶性生成物をブフナー漏斗でワットマン54番濾紙を用いて回収した。青色の生成物を一晩風乾した後、60℃の真空オーブン内で3時間乾燥させた。青色の粉末である回収された生成物の重量は7.8gであった。融点:310℃超。赤外分光法(ダイヤモンドアンビル)、マススペクトル(MALDI−TOF)、原子発光分析法及び元素分析による生成物の特性化及び分析から、所望の生成物の生成が失敗したことが示された。回収されたクロロアルミニウムテトラフルオロフタロシアニン及びヒドロキシアルミニウムテトラフルオロフタロシアニンを単離した。
100mL容の一口丸底フラスコに、4.7g(7.2mmol)のクロロアルミニウムテトラフルオロフタロシアニン、1.72g(7.6mmol)の1,4−ビス(ヒドロキシジメチルシリル)ベンゼン及び35mLのピリジンをこの順序で入れた。フラスコにマグネチックスターラーバーを入れ、冷却器及び窒素注入口を取り付けた。フラスコを130℃に予熱した油浴内に入れた。反応を撹拌し、還流下で一晩加熱した。フラスコを油浴から取り出し、約50℃まで冷却した後、約40mLのアセトンを添加し、混合物を室温で15分間撹拌した。不溶性生成物をブフナー漏斗上で回収し、アセトンで洗った。風乾させた明るいシアンブルーの粗生成物の重量は4.6gであった。この粗生成物を250mL容の三角フラスコに入れ、ガラス撹拌棒で粉砕した。フラスコに150mLのアセトンを添加した後、混合物をホットプレート上で30分間、磁気攪拌しながら還流温度で加熱した。不溶性生成物をブフナー漏斗でのワットマン54番濾紙を通した熱濾過によって回収した。生成物を50℃の真空オーブン内で5日間乾燥させた。回収された青色の粉末生成物Inv−9の重量は4.52gであった(3.1mmol、理論値の86.1%)。生成物をマススペクトル(MALDI)によって特性化した:理論値:m/z 1446.3;実測値:m/z 1446.3。生成物は少量の残留未反応クロロアルミニウムテトラフルオロフタロシアニンを含有していた。
水性ミル粉砕物を以下の処方を用いて調製した:
1gの顔料(初めにTekmarの粉砕機を用いて5分間乾式粉砕した);
7.5gの10%N−メチル−N−オレイルタウリン酸カリウム水溶液;
6.5gの蒸留水;
70gの0.2mm径ケイ酸ジルコニウムセラミックビーズ;
続いて2100rpmで24時間、水冷しながら粉砕した。
本発明例A:特別に設計したバッフルを備えた1L容のステンレス製冷水ジャケット付き容器に、プロピレングリコールモノメチルエーテルアセテート(PGMEA)及びシクロヘキサノンからなる1:1(w/w)の溶媒混合物244gを、11.25gの分散剤ポリマーSolsperse 41000と共に導入した。次いで、Caframoの垂直メカニカルスターラーに接続した50mm径工具鋼Dブレードを溶媒中に沈めた。スターラーを500rpmで作動させながら、45gのInv−1、続いて600gの0.2mm Zirstar(ケイ酸ジルコニウム粉砕媒体)を添加した。得られた分散液を、混合速度を漸増させることによって(1600rpm/18時間から始め、次いで2800rpm/6時間に上げ、2800rpm/18時間に保ち、3000rpm/5時間で終える)粉砕した。分散液を20ミクロンフィルタを通した加圧濾過によって粉砕媒体から分離した後、単離した。
本発明例Cを以下のようにして調製した。特別に設計したバッフルを備えた1L容のステンレス製冷水ジャケット付き容器に、7.5gの分散剤ポリマーDisperbyk−111、及びプロピレングリコールモノメチルエーテルアセテートとシクロヘキサノンとの1:1(w/w)の混合物129gを充填した。次いで、Caframoの垂直メカニカルスターラーに接続した50mm径工具鋼Dブレードを溶媒中に沈めた。スターラーを500rpmで作動させながら、13.5gのInv−1、続いて150gの50ミクロンポリスチレン粉砕媒体を添加した。分散液を、1600rpm/17時間、2200rpm/3時間、2400rpm/2時間及び2500rpm/4時間という順序を用いて混合速度を漸増させることによって粉砕した。動的光散乱サイジング法を用いてナノ粒子の形成が確認された後、粉砕を中止した。
Claims (17)
- n=1であり、R1及びR2の両方が同一であり、R3が酸素又はアリールであり、zが1〜4である請求項1に記載の顔料。
- R1及びR2の両方がフェニル基である請求項2に記載の顔料。
- zが1である請求項3に記載の顔料。
- zが4である請求項3に記載の顔料。
- シリルジオールとハロアルミニウムフルオロフタロシアニン化合物との反応によって調製される請求項1に記載の顔料。
- 水性媒体中に分散された請求項1に記載の顔料。
- 硫酸塩、スルホン酸塩、アクリルコポリマー、スチレン−アクリルコポリマー、スルホン化ポリエステル、スルホン化スチレン類、リン含有ポリエステル及びリン含有スチレン類から選択される分散剤を含有する請求項7に記載の分散液。
- 有機液体中に分散された請求項1に記載の顔料。
- 顔料粒子の少なくとも85容量%が2750nm未満の粒径を有する請求項9に記載の顔料分散液。
- 顔料粒子の少なくとも80容量%が100nm未満の粒径を有する請求項19に記載の顔料分散液。
- 前記有機液体が、ケトン、炭化水素、アルコール、ポリオール、エーテル及びエステルから選択される請求項9に記載の分散液。
- Solsperse 41000、Disperbyk−111、Disperbyk−161、硫酸塩、スルホン酸塩、アクリルコポリマー、スチレン−アクリルコポリマー、スルホン化ポリエステル、スルホン化スチレン類、リン含有ポリエステル、並びにアミン官能基又はポリエーテル官能基を含有する分散剤から選択される分散剤を含有する請求項9に記載の分散液。
- 水性媒体中に分散された請求項3に記載の顔料。
- 有機液体中に分散された請求項3に記載の顔料。
- 顔料粒子の少なくとも85容量%が2750nm未満の粒径を有する請求項15に記載の顔料分散液。
- 顔料粒子の少なくとも80容量%が100nm未満の粒径を有する請求項15に記載の顔料分散液。
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PCT/US2009/005829 WO2010053510A2 (en) | 2008-10-29 | 2009-10-27 | Fluorinated bis-(phthalocyanylaluminoxy)silyl pigments |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011089016A (ja) * | 2009-10-22 | 2011-05-06 | Toyo Ink Mfg Co Ltd | 緑色着色組成物、カラーフィルタおよびカラー表示装置 |
JP2012507743A (ja) * | 2008-10-29 | 2012-03-29 | グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー | 改良された着色剤分散物をもつカラーフィルタエレメント |
JP2012247588A (ja) * | 2011-05-27 | 2012-12-13 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色組成物、およびカラーフィルタ |
JP2019214672A (ja) * | 2018-06-13 | 2019-12-19 | 東洋インキScホールディングス株式会社 | 着色組成物、カラーフィルタおよび液晶表示装置 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010163473A (ja) * | 2009-01-13 | 2010-07-29 | Konica Minolta Business Technologies Inc | インクジェット記録用シアンインク |
US9738801B2 (en) | 2010-10-29 | 2017-08-22 | Hewlett-Packard Development Company, L.P. | Metallic LEP inks and associated methods |
US8927185B2 (en) | 2012-08-22 | 2015-01-06 | Canon Kabushiki Kaisha | Toner and toner production method |
WO2015063692A1 (en) * | 2013-10-31 | 2015-05-07 | Sabic Global Technologies B.V. | Process for making axially fluorinated-phthalocyanines and their use in photovoltaic applications |
US9260630B2 (en) * | 2014-04-03 | 2016-02-16 | Porter Scientific, Inc. | Self-cleaning protective coatings |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5790058A (en) * | 1980-10-06 | 1982-06-04 | Eastman Kodak Co | Novel phthalocyanine pigment |
JPS63141982A (ja) * | 1986-12-05 | 1988-06-14 | Nippon Shokubai Kagaku Kogyo Co Ltd | フタロシアニンヘキサデカフルオリド類化合物 |
EP0860475A1 (en) * | 1997-02-21 | 1998-08-26 | Eastman Kodak Company | Synthesis of bis(Phthalocyanylalumino)tetraphenyldisiloxanes |
JP2012507592A (ja) * | 2008-10-29 | 2012-03-29 | グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー | フッ素化フタロシアニン顔料のナノ分散物の調製方法 |
Family Cites Families (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2227628A (en) | 1938-06-30 | 1941-01-07 | Du Pont | Fluorination of phthalocyanines |
US4209458A (en) | 1979-04-04 | 1980-06-24 | The United States Of America As Represented By The Secretary Of The Navy | Fluorinated phthalonitriles |
US4382033A (en) * | 1980-10-06 | 1983-05-03 | Eastman Kodak Company | Novel phthalocyanine pigments |
CH654121A5 (de) | 1983-03-25 | 1986-01-31 | Ciba Geigy Ag | Verfahren zur herstellung von festen photoaktivatorpraeparaten. |
US4701396A (en) | 1986-05-06 | 1987-10-20 | Eastman Kodak Company | Photoconductive phthalocyanine pigments, electrophotographic elements containing them and a method of use |
WO1987007267A1 (en) | 1986-05-19 | 1987-12-03 | Allied Corporation | Method of synthesizing tetrafluorophthalonitrile |
US4892941A (en) | 1987-04-17 | 1990-01-09 | Dolphin David H | Porphyrins |
JPH0778182B2 (ja) * | 1988-09-08 | 1995-08-23 | 三井東圧化学株式会社 | ナフタロシアニンポリマー及びそれを用いた光記録媒体 |
US6238931B1 (en) * | 1993-09-24 | 2001-05-29 | Biosite Diagnostics, Inc. | Fluorescence energy transfer in particles |
US7083984B2 (en) * | 1993-09-24 | 2006-08-01 | Biosite, Inc. | Hybrid phthalocyanine derivatives and their uses |
US6964844B1 (en) * | 1993-09-24 | 2005-11-15 | Biosite, Inc. | Hybrid phthalocyanine derivatives and their uses |
US5466796A (en) * | 1994-04-26 | 1995-11-14 | Xerox Corporation | Alkoxy-bridged metallophthalocyanine dimers |
US5441837A (en) | 1994-07-29 | 1995-08-15 | Xerox Corporation | Photoconductive imaging members with acetoxymetal phthalocyanines |
US5614342A (en) | 1995-05-02 | 1997-03-25 | Eastman Kodak Company | Methods for preparing cocrystals of titanyl fluorophthalocyanines and unsubstituted titanyl phthalocyanine, electrophotographic elements, and titanyl phthalocyanine compositions |
US5773181A (en) | 1995-05-23 | 1998-06-30 | Eastman Kodak Company | Non-uniformly substituted phthalocyanine compositions preparation methods, and electrophotographic elements |
US5679142A (en) * | 1996-08-20 | 1997-10-21 | Eastman Kodak Company | Cyan ink jet pigment set |
US5679139A (en) | 1996-08-20 | 1997-10-21 | Eastman Kodak Company | Cyan and magenta pigment set |
US5738716A (en) | 1996-08-20 | 1998-04-14 | Eastman Kodak Company | Color pigmented ink jet ink set |
EP0889097B1 (en) | 1996-10-14 | 2005-06-29 | Nippon Shokubai Co., Ltd. | Phthalocyanine compounds, process for preparing the same, and optical recording medium made using the same |
EP0848045B1 (en) * | 1996-12-13 | 2001-01-10 | Eastman Kodak Company | Pigmented inkjet inks containing phosphated ester derivatives |
US6051702A (en) | 1997-05-08 | 2000-04-18 | Rutgers, The University Of New Jersey | Organic dyes for photovoltaic cells and for photoconductive electrophotography systems |
US6152999A (en) | 1999-04-27 | 2000-11-28 | Eastman Kodak Company | Color pigmented ink jet set |
US6153000A (en) | 1999-07-12 | 2000-11-28 | Eastman Kodak Company | Color pigmented ink jet ink set |
US6716897B2 (en) | 2000-12-22 | 2004-04-06 | Toyo Ink Mfg. Co., Ltd. | Colored composition for color filter and color filter |
US20030027893A1 (en) * | 2001-06-28 | 2003-02-06 | Eastman Kodak Company | Ink jet printing method |
US6726755B2 (en) | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
US7382514B2 (en) | 2002-02-11 | 2008-06-03 | Sipix Imaging, Inc. | Core-shell particles for electrophoretic display |
TWI329662B (en) | 2002-05-17 | 2010-09-01 | Sipix Imaging Inc | Novel fluorinated silicon (iv) phthalocyanines and naphthalocyanines for electrophoretic, magnetophoretic or electromagnetophoretic display |
JP4321013B2 (ja) * | 2002-06-25 | 2009-08-26 | セイコーエプソン株式会社 | アルミニウムフタロシアニン顔料組成物及びこれを用いた画像記録物質 |
US6715869B1 (en) * | 2002-11-19 | 2004-04-06 | Eastman Kodak Company | Ink set for ink jet printing |
US6949139B2 (en) | 2002-12-02 | 2005-09-27 | Eastman Kodak Company | Process for forming cocrystals containing chlorine-free titanyl phthalocyanines and low concentration of titanyl fluorophthalocyanine using organic milling aid |
WO2005033110A1 (en) | 2003-10-07 | 2005-04-14 | York University | Processes for producing polysubstituted phythalocyanines |
US7572394B2 (en) | 2003-11-04 | 2009-08-11 | Sipix Imaging, Inc. | Electrophoretic dispersions |
JP2005298490A (ja) * | 2004-03-19 | 2005-10-27 | Toyo Ink Mfg Co Ltd | フタロシアニン化合物及びこれを用いた有機色素、光記録媒体 |
US7211359B2 (en) | 2004-04-30 | 2007-05-01 | Eastman Kodak Company | Coating solution containing cocrystals and or crystals of a charge-generation pigment or a mixture of charge-generation pigments |
US20050272831A1 (en) * | 2004-06-04 | 2005-12-08 | Eastman Kodak Company | Aqueous inkjet ink compositon |
US20060014855A1 (en) | 2004-07-14 | 2006-01-19 | Eastman Kodak Company | Pigment dispersion with polymeric dispersant |
KR100882503B1 (ko) | 2004-10-06 | 2009-02-06 | 한국과학기술연구원 | 염료감응 태양전지용 고효율 대향전극 및 그 제조방법 |
US7973902B2 (en) | 2006-11-10 | 2011-07-05 | Global Oled Technology Llc | Display with RGB color filter element sets |
US7837780B2 (en) | 2006-11-10 | 2010-11-23 | Global Oled Technology Llc | Green color filter element |
EP1936441B1 (en) * | 2006-12-21 | 2010-03-10 | Konica Minolta Business Technologies, Inc. | Electrostatic image developing toner |
-
2008
- 2008-10-29 US US12/260,344 patent/US7628849B1/en active Active
-
2009
- 2009-10-27 CN CN200980143035.8A patent/CN102197096B/zh active Active
- 2009-10-27 WO PCT/US2009/005829 patent/WO2010053510A2/en active Application Filing
- 2009-10-27 KR KR1020117009241A patent/KR101235780B1/ko active IP Right Grant
- 2009-10-27 JP JP2011534503A patent/JP5174247B2/ja active Active
- 2009-10-27 EP EP09744238.8A patent/EP2361284B1/en active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5790058A (en) * | 1980-10-06 | 1982-06-04 | Eastman Kodak Co | Novel phthalocyanine pigment |
JPS63141982A (ja) * | 1986-12-05 | 1988-06-14 | Nippon Shokubai Kagaku Kogyo Co Ltd | フタロシアニンヘキサデカフルオリド類化合物 |
EP0860475A1 (en) * | 1997-02-21 | 1998-08-26 | Eastman Kodak Company | Synthesis of bis(Phthalocyanylalumino)tetraphenyldisiloxanes |
JP2012507592A (ja) * | 2008-10-29 | 2012-03-29 | グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー | フッ素化フタロシアニン顔料のナノ分散物の調製方法 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012507743A (ja) * | 2008-10-29 | 2012-03-29 | グローバル・オーエルイーディー・テクノロジー・リミテッド・ライアビリティ・カンパニー | 改良された着色剤分散物をもつカラーフィルタエレメント |
JP2011089016A (ja) * | 2009-10-22 | 2011-05-06 | Toyo Ink Mfg Co Ltd | 緑色着色組成物、カラーフィルタおよびカラー表示装置 |
JP2012247588A (ja) * | 2011-05-27 | 2012-12-13 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用着色組成物、およびカラーフィルタ |
JP2019214672A (ja) * | 2018-06-13 | 2019-12-19 | 東洋インキScホールディングス株式会社 | 着色組成物、カラーフィルタおよび液晶表示装置 |
JP7234513B2 (ja) | 2018-06-13 | 2023-03-08 | 東洋インキScホールディングス株式会社 | 着色組成物、カラーフィルタおよび液晶表示装置 |
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US7628849B1 (en) | 2009-12-08 |
WO2010053510A3 (en) | 2010-08-19 |
TW201030101A (en) | 2010-08-16 |
TWI394804B (zh) | 2013-05-01 |
EP2361284B1 (en) | 2013-05-01 |
KR20110087267A (ko) | 2011-08-02 |
CN102197096B (zh) | 2014-04-16 |
EP2361284A2 (en) | 2011-08-31 |
JP5174247B2 (ja) | 2013-04-03 |
WO2010053510A2 (en) | 2010-05-14 |
KR101235780B1 (ko) | 2013-02-22 |
CN102197096A (zh) | 2011-09-21 |
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