JP6479871B2 - 金属アゾ顔料 - Google Patents
金属アゾ顔料 Download PDFInfo
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- JP6479871B2 JP6479871B2 JP2017055772A JP2017055772A JP6479871B2 JP 6479871 B2 JP6479871 B2 JP 6479871B2 JP 2017055772 A JP2017055772 A JP 2017055772A JP 2017055772 A JP2017055772 A JP 2017055772A JP 6479871 B2 JP6479871 B2 JP 6479871B2
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- metal
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- 239000000049 pigment Substances 0.000 title claims description 190
- 229910052751 metal Inorganic materials 0.000 title claims description 115
- 239000002184 metal Substances 0.000 title claims description 115
- 239000011701 zinc Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 78
- 229910021645 metal ion Inorganic materials 0.000 claims description 65
- 239000010949 copper Substances 0.000 claims description 63
- 238000002360 preparation method Methods 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 16
- 229910052725 zinc Inorganic materials 0.000 claims description 16
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 15
- 150000001879 copper Chemical class 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002270 dispersing agent Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 229920002120 photoresistant polymer Polymers 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 150000003751 zinc Chemical class 0.000 claims description 9
- 239000000976 ink Substances 0.000 claims description 8
- 238000004040 coloring Methods 0.000 claims description 7
- 239000004973 liquid crystal related substance Substances 0.000 claims description 7
- 238000007639 printing Methods 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 4
- 239000000123 paper Substances 0.000 claims description 4
- 239000004753 textile Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 229920002994 synthetic fiber Polymers 0.000 claims description 2
- 208000000655 Distemper Diseases 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 229920005615 natural polymer Polymers 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229920001059 synthetic polymer Polymers 0.000 claims 1
- 239000004758 synthetic textile Substances 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 39
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 26
- -1 azo compound Chemical class 0.000 description 26
- 239000000203 mixture Substances 0.000 description 24
- 239000011347 resin Chemical class 0.000 description 22
- 229920005989 resin Chemical class 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- 229920000877 Melamine resin Polymers 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 239000011651 chromium Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000009830 intercalation Methods 0.000 description 6
- 230000002687 intercalation Effects 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- LCGWXMONLSJYQR-UHFFFAOYSA-N 5-[(2,4,6-trioxo-1,3-diazinan-5-yl)diazenyl]-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1N=NC1C(=O)NC(=O)NC1=O LCGWXMONLSJYQR-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 229910052689 Holmium Inorganic materials 0.000 description 4
- 229920001732 Lignosulfonate Polymers 0.000 description 4
- 229910052779 Neodymium Inorganic materials 0.000 description 4
- 229910052777 Praseodymium Inorganic materials 0.000 description 4
- 229910052772 Samarium Inorganic materials 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052771 Terbium Inorganic materials 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 150000003857 carboxamides Chemical class 0.000 description 4
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 4
- 239000006069 physical mixture Substances 0.000 description 4
- 239000004800 polyvinyl chloride Substances 0.000 description 4
- 229920000915 polyvinyl chloride Polymers 0.000 description 4
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 4
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 4
- 150000003505 terpenes Chemical class 0.000 description 4
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 229910052692 Dysprosium Inorganic materials 0.000 description 3
- 229910052691 Erbium Inorganic materials 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052693 Europium Inorganic materials 0.000 description 3
- 229910052688 Gadolinium Inorganic materials 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229910052775 Thulium Inorganic materials 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052769 Ytterbium Inorganic materials 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229910052746 lanthanum Inorganic materials 0.000 description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 3
- 239000010955 niobium Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229910052706 scandium Inorganic materials 0.000 description 3
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052720 vanadium Inorganic materials 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical compound C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- QMDBZGCCRMDYKZ-UHFFFAOYSA-N 2,3-dioxo-1,4-dihydroquinoxaline-6-sulfonic acid Chemical compound N1C(=O)C(=O)NC2=CC(S(=O)(=O)O)=CC=C21 QMDBZGCCRMDYKZ-UHFFFAOYSA-N 0.000 description 2
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- MCWCROLXQGCRCL-UHFFFAOYSA-N 9h-carbazole-3,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C3=CC(S(=O)(=O)O)=CC=C3NC2=C1 MCWCROLXQGCRCL-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/48—Preparation from other complex metal compounds of azo dyes
- C09B45/485—Copper complexes
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- C09B45/00—Complex metal compounds of azo dyes
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- C09B45/14—Monoazo compounds
- C09B45/22—Monoazo compounds containing other metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/0091—Complexes with metal-heteroatom-bonds
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- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
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- C09B45/00—Complex metal compounds of azo dyes
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- C09B45/18—Monoazo compounds containing copper
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- C09B45/00—Complex metal compounds of azo dyes
- C09B45/48—Preparation from other complex metal compounds of azo dyes
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0002—Grinding; Milling with solid grinding or milling assistants
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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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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0025—Crystal modifications; Special X-ray patterns
- C09B67/0028—Crystal modifications; Special X-ray patterns of azo compounds
- C09B67/0029—Crystal modifications; Special X-ray patterns of azo compounds of monoazo compounds
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
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- C—CHEMISTRY; METALLURGY
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
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- C09D11/00—Inks
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- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- C09D11/00—Inks
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- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
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- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
- C09D5/028—Pigments; Filters
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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Description
a)金属のタイプの点で少なくとも異なり、そしてそれぞれ
・ 式(I)の構造単位、またはそれらの互変異性型
R1およびR2はそれぞれ独立して、OH、NH2またはNHR5であり、
R3およびR4はそれぞれ独立して、=Oまたは=NR5であり、
R5は、水素またはアルキル、好ましくはC1〜C4アルキルである)
ならびに
・ Zn2+および/またはCu2+金属イオンならびに任意選択により場合によっては少なくとも1つのさらなる金属イオンMe(ここで、Meは、Zn2+およびCu2+以外の二価もしくは三価の金属イオンであり、ただし、いずれの場合にも金属アゾ顔料中の全金属イオンの量の合計100%を基準として、Zn2+およびCu2+金属イオンを一緒にした量は、95〜100%であり、Zn2+およびCu2+以外の二価もしくは三価の金属イオンの量は、0〜5%であり、
ここで、金属アゾ顔料中のZn2+対Cu2+金属イオンのモル比は、199:1〜1:15、好ましくは19:1〜1:1、より好ましくは9:1〜2:1である)
を含有する少なくとも2つの金属アゾ化合物と、
b)式(II)
R6は、水素またはアルキル、好ましくはOHによって任意選択により場合によってはモノもしくは多置換されていてもよいC1〜C4アルキルである)
の少なくとも1つの化合物と
を含むことを特徴とする、金属アゾ顔料に関する。
ここ及び以下において、上記金属イオンの量は以下の式:(その金属イオンのモル量にその金属イオンの価数を乗じた値)÷(Zn 2+ 、Cu 2+ 、及びMeの全ての金属イオンについて、前記の金属イオンのモル量にその金属イオンの価数を乗じた値を合計した値)によって得られる値に基づく、金属アゾ顔料中に含まれる全ての金属イオンの値の合計を100%として計算される量である。
(式中、R1およびR2はOHであり、
R3およびR4は=Oである)
の構造単位
ならびに
Zn2+および/またはCu2+金属イオンならびに任意選択により場合によっては少なくとも1つのさらなる金属イオンMe
(ここで、
Meは、Ni2+、Al3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd2+、Nd3+、Sm2+、Sm3+、Eu2+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb2+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、Y3+、Sc3+、Ti2+、Ti3+、Nb3+、Mo2+、Mo3+、V2+、V3+、Zr2+、Zr3+、Cd2+、Cr3+、Pb2+、Ba2+の群から、より好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、Y3+の群から、最も好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Tb3+、Ho3+、Sr2+の群から、とりわけAl3+、Fe2+、Fe3+、Co2+およびCo3+の群から選択される金属イオンであり
ただし、いずれの場合にも金属アゾ顔料中の全金属イオンの上記式で計算される量の合計100%を基準として、Zn2+およびCu2+金属イオンを一緒にした量は、95〜100%であり、金属イオンMeの量は、0〜5%であり、
そして
ここで、金属アゾ顔料中のZn2+対Cu2+金属イオンの上記式で計算される量の比は、199:1〜1:15、好ましくは19:1〜1:1、より好ましくは9:1〜2:1である)
を含有する少なくとも2つの金属アゾ化合物と、
b)上に規定された式(II)
(式中、
R6は水素である)
の少なくとも1つの化合物と
の付加体を含む金属アゾ顔料が好ましい。
(式中、
R1、R2、R3、R4およびR5は、上に規定された一般的な、好ましい定義を有する)
の構造単位を含有し、
そして
Zn2+および/またはCu2+金属イオン
(ただし、Zn2+およびCu2+金属イオンを一緒にした量は、金属アゾ顔料中の全金属イオンの量100%を基準として、100%であり
ここで、金属アゾ顔料中のZn2+対Cu2+金属イオンの上記式で計算される量の比は、199:1〜1:15、好ましくは19:1〜1:1、より好ましくは9:1〜2:1である)
を含有する少なくとも2つの金属アゾ化合物と、
b)上に規定された式(II)(式中、
R6は、上に規定された一般的な、好ましい定義を有する)
の少なくとも1つの化合物と
の付加体を含む金属アゾ顔料が特に好ましい。
Xは、アルカリ金属イオン、好ましくはナトリウムもしくはカリウムイオンであり、
R1およびR2はそれぞれ独立して、OH、NH2またはNHR5であり、
R3およびR4はそれぞれ独立して、=Oまたは=NR5であり、
R5は、水素またはアルキル、好ましくはC1〜C4アルキルである)
の少なくとも1つの化合物、またはその互変異性体が、
式(II)の少なくとも1つの化合物の存在下で、少なくとも1つの亜鉛塩および少なくとも1つの銅塩と、ならびに任意選択により場合によっては、好ましくはNi2+、Al3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd2+、Nd3+、Sm2+、Sm3+、Eu2+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb2+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、Y3+、Sc3+、Ti2+、Ti3+、Nb3+、Mo2+、Mo3+、V2+、V3+、Zr2+、Zr3+、Cd2+、Cr3+、Pb2+およびBa2+塩の群から、より好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+およびY3+塩の群から、最も好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Tb3+、Ho3+およびSr2+塩の群から、とりわけAl3+、Fe2+、Fe3+、Co2+およびCo3+塩の群からの、亜鉛および銅以外の二価もしくは三価の金属の少なくとも1つのさらなる金属塩と同時にもしくは順次反応させられ、
ここで、0.06〜0.995モルの少なくとも1つの亜鉛塩、0.005〜0.94モルの少なくとも1つの銅塩ならびに0.05〜0モルの亜鉛および銅以外の二価もしくは三価の金属の少なくとも1つのさらなる金属塩が、式(III)の化合物1モル当たり使用され、そしてここで、全てのこれらの金属塩を一緒にしたモル量の合計が1モルであることを特徴とする、本発明の金属アゾ顔料の製造方法を提供する。
のモノアルカリ金属化合物、もしくはその互変異性体、
または式(III)および(IIIa)の化合物の混合物を使用することもまた可能である。これらのケースでは、亜鉛および銅塩ならびに亜鉛および銅塩以外の任意のさらなる金属塩の、そして式(II)の化合物の述べられるモル量は、使用される化合物(III)および(IIIa)のモル量の合計に関係している。
(i)a1)上に規定された式(I)
(式中、
R1、R2、R3、R4およびR5は、上に規定された一般的な、好ましい定義を有する)
の構造単位、
ならびに
Cu2+イオン
を含有する金属アゾ化合物と、
b1)上に規定された式(II)(式中、R6は、上に与えられた一般的な、好ましい定義を有する)の少なくとも1つの化合物と
の少なくとも1つの付加体
(そしてCu2+金属イオンの量は、付加体a1)/b1)中の全金属イオンの1モルを基準として、100モル%である)と、
(ii)a2)上に規定された式(I)
(式中、
R1、R2、R3、R4およびR5は、上に規定された一般的な、好ましい定義を有する)
の構造単位、
ならびに
Zn2+イオン
を含有する金属アゾ顔料と、
b2)上に規定された式(II)(式中、R6は、上に与えられた一般的な、好ましい定義を有する)の少なくとも1つの化合物と
の少なくとも1つの付加体
(そしてZn2+金属イオンの量は、付加体a2)/b2)中の全金属イオン1モルを基準として、100モル%である)と、
任意選択により場合によっては
(iii)a3)上に規定された式(I)
(式中、
R1、R2、R3、R4およびR5は、上に規定された一般的な、好ましい定義を有する)
の構造単位、
ならびに
金属イオンMe
(ここで、
Meは、Zn2+およびCu2+以外の二価もしくは三価の金属イオン、好ましくはNi2+、Al3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd2+、Nd3+、Sm2+、Sm3+、Eu2+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb2+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、Y3+、Sc3+、Ti2+、Ti3+、Nb3+、Mo2+、Mo3+、V2+、V3+、Zr2+、Zr3+、Cd2+、Cr3+、Pb2+、Ba2+の群から、より好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、Y3+の群から、最も好ましくはAl3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Tb3+、Ho3+、Sr2+の群から、とりわけAl3+、Fe2+、Fe3+、Co2+およびCo3+の群から選択される金属イオンである)
を含有する金属アゾ化合物と、
b3)上に規定された式(II)(式中、R6は、上に与えられた一般的な、好ましい定義を有する)の少なくとも1つの化合物と
の少なくとも1つの付加体
(そしてMe金属イオンの量は、付加体a3)/b3)中の全金属イオン1モルを基準として、100モル%である)と
が互いに混合され、ここで、付加体a1)/b1)およびa2)/b2)のモル量の合計を基準として、付加体a1)/b1)の1モル当たり0.005〜15モルの付加体a2)/b2)が使用され、かつ0〜0.05モルの付加体a3)/b3)が使用されることを特徴とする、本発明の金属アゾ顔料の製造方法を提供する。
1)6〜22個の炭素原子を有する飽和および/もしくは不飽和脂肪アルコールまたは
2)アルキル基中に4〜12個の炭素原子を有するアルキルフェノールまたは
3)14〜20個の炭素原子を有する飽和および/もしくは不飽和脂肪アミンまたは
4)14〜20個の炭素原子を有する飽和および/もしくは不飽和脂肪酸または
5)水素化および/もしくは非水素化樹脂酸
との反応生成物類からのエチレンオキシド付加体である。
R15は、水素またはC1〜C4アルキルであり、
R16は、水素またはCH3であり、
R17は、水素、C1〜C4アルキル、C1〜C4アルコキシ、C1〜C4アルコキシカルボニルまたはフェニルであり、
mは、1〜4の数であり、
nは、6〜120の数であり、
R18は、nによって示されるあらゆる単位について同じもしくは異なるものであり、そして水素、CH3またはフェニルであり、ここで、CH3が異なる−(−CH2−CH(R18)−O−)基の幾つかに存在する場合には、R18は、nの合計値の0%〜60%でCH3であり、R18は、nの合計値の100%〜40%で水素であり、そしてここで、フェニルが異なる−(−CH2−CH(R18)−O−)基の幾つかに存在するケースでは、R18は、nの合計値の0%〜40%でフェニルであり、R18は、nの合計値の100%〜60%で水素である。)
R15’、R16’、R17’、R18’、m’およびn’は、R15、R16、R17、R18、mおよびnの定義の範囲を前提とするが独立であって、
Xは、−SO3、−SO2、−PO3または−CO−(R19)−COO基であり、
Katは、H、Li、Na、K、NH4またはHO−CH2CH2−NH3の群からのカチオンであり、ここで、X=−PO3のケースでは、2つのKatが存在し、
R19は、二価の脂肪族または芳香族基、好ましくはC1〜C4アルキレン、とりわけエチレン、C2〜C4モノ不飽和基、とりわけアセチレン、または任意選択により置換されていてもよいフェニレン、とりわけオルト−フェニレンであり、ここで、可能な置換基には好ましくは、C1〜C4アルキル、C1〜C4アルコキシ、C1〜C4アルコキシカルボニル、またはフェニルが含まれる)
に相当する。
50重量%〜99重量%の本発明の少なくとも1つの金属アゾ顔料と、
1重量%〜50重量%、好ましくは2重量%〜50重量%の成分(d)の少なくとも1つの化合物と
を含む。
− 本発明の少なくとも1つの金属アゾ顔料と、
− 任意選択により場合によってはバインダー樹脂と、
− 少なくとも1つの有機溶媒と、
− 任意選択により場合によっては分散剤と
を含む「配合物」を生み出す。
1重量%〜50重量%の本発明の金属アゾ顔料
0重量%〜20重量%のバインダー樹脂
0重量%〜20重量%の分散剤
10重量%〜94重量%の有機溶媒
を含有する。
Colour Index(カラーインデックス)Pigment Yellow 12、13、14、17、20、24、74、83、86、93、94、109、110、117、125、137、138、139、147、148、150、153、154、166、173、185、または
Colour Index Pigment Orange 13、31、36、38、40、42、43、51、55、59、61、64、65、71、72、73または
Colour Index Pigment Red 9、97、122、123、144、149、166、168、177、180、192、215、216、224、254、272、または
Colour Index Pigment Green 7、10、36、37、45、58または
Colour Index Pigment Blue 15、15:1、15:2、15:3、15:4、15:6、16および
Colour Index Pigment Violet 19、23
である。
さらに、そのようなバインダー樹脂はまた、遊離のイソシアネート基を有する不飽和化合物を含有してもよい。
A)とりわけ他の顔料、好ましくはC.I.Pigment Green 36および/もしくはPigment Green 58との混合物での、本発明の少なくとも1つの金属アゾ顔料またはそれをベースとする顔料調製物と、
B1)少なくとも1つの光硬化性モノマーと、
B2)少なくとも1つの光開始剤と、
C1)任意選択により場合によっては有機溶媒と、
D)任意選択により場合によっては分散剤と、
E)任意選択により場合によってはバインダー樹脂と、
任意選択により場合によってはさらなる添加物と
を含むフォトレジストに関する。
46.2gのジアゾバルビツール酸および38.4gのバルビツール酸を、85℃で1100gの蒸留水へ導入する。続いて、水性水酸化カリウム溶液を使用して約5のpHを確立し、混合物を90分間攪拌した。
1500gの蒸留水を、方法1に従って製造されたアゾバルビツール酸に82℃で添加した。その後、75.7gのメラミンを導入した。続いて、0.3モルの約30%塩化銅(II)溶液を滴下により添加した。82℃で3時間後に、KOHを使用して約5.5のpHを確立した。その後、希釈を約300gの蒸留水で90℃にて達成した。続いて、34gの30%塩酸を滴下により添加し、混合物を90℃で12時間熱処理した。その後、水性水酸化カリウム溶液を使用して約5のpHを確立した。続いて、顔料を吸引フィルター上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させ、標準実験室ミルで約2分間すり潰した(=顔料A)。
1500gの蒸留水を、方法1に従って製造されたアゾバルビツール酸に82℃で添加した。続いて、10gの30%塩酸を滴下により添加した。その後、79.4gのメラミンを導入した。続いて、0.3モルの約25%塩化亜鉛溶液を滴下により添加した。82℃で3時間後に、KOHを使用して約5.5のpHを確立した。その後、希釈を100gの蒸留水で90℃にて達成した。続いて、21gの30%塩酸を滴下により添加し、混合物を90℃で12時間熱処理した。その後、水性水酸化カリウム溶液を約5のpHへの調整のために使用した。続いて、顔料を吸引フィルター上で単離し、洗浄し、80℃での真空乾燥キャビネット中で乾燥させ、標準実験室ミルで約2分間すり潰した(=顔料B)。
以下に続く本発明の実施例3〜15は、実施例2と類似の方法で製造した。塩化亜鉛溶液を、塩化亜鉛と塩化銅(II)との混合溶液でいずれの場合にも置き換えた。
実施例3:0.3モルのZnを0.282モルのZn+0.0015モルのCuで置き換えた(=顔料C)
実施例4:0.3モルのZnを0.282モルのZn+0.006モルのCuで置き換えた(=顔料D)
実施例5:0.3モルのZnを0.282モルのZn+0.018モルのCuで置き換えた(=顔料E)
実施例6:0.3モルのZnを0.270モルのZn+0.030モルのCuで置き換えた(=顔料F)
実施例7:0.3モルのZnを0.240モルのZn+0.060モルのCuで置き換えた(=顔料G)
実施例8:0.3モルのZnを0.210モルのZn+0.090モルのCuで置き換えた(=顔料H)
実施例9:0.3モルのZnを0.180モルのZn+0.120モルのCuで置き換えた(=顔料I)
実施例10:0.3モルのZnを0.150モルのZn+0.150モルのCuで置き換えた(=顔料J)
実施例11:0.3モルのZnを0.120モルのZn+0.120モルのCuで置き換えた(=顔料K)
実施例12:0.3モルのZnを0.090モルのZn+0.210モルのCuで置き換えた(=顔料L)
実施例13:0.3モルのZnを0.060モルのZn+0.240モルのCuで置き換えた(=顔料M)
実施例14:0.3モルのZnを0.030モルのZn+0.270モルのCuで置き換えた(=顔料N)
実施例15:0.3モルのZnを0.018モルのZn+0.282モルのCuで置き換えた(=顔料O)
実施例16:0.3モルのZnを0.270モルのZn+0.015モルのCu+0.015モルのNiで置き換えた(=顔料AA)
実施例17:0.3モルのZnを0.270モルのZn+0.015モルのCu+0.015モルのCdで置き換えた(=顔料AB)
実施例18:0.3モルのZnを0.270モルのZn+0.015モルのCu+0.0075モルのFe+0.0075モルのPbで置き換えた(=顔料AC)
実施例19:0.3モルのZnを0.270モルのZn+0.015モルのCu+0.006モルのNi+0.004モルのCr+0.003モルのFeで置き換えた(=顔料AD)
実施例20:0.3モルのZnを0.150モルのZn+0.135モルのCu+0.015モルのCdで置き換えた(=顔料AE)
実施例21:0.3モルのZnを0.150モルのZn+0.135モルのCu+0.010モルのCrで置き換えた(=顔料AF)
実施例22:0.3モルのZnを0.150モルのZn+0.135モルのCu+0.0075モルのCo+0.0075モルのPbで置き換えた(=顔料AG)
実施例23:0.3モルのZnを0.150モルのZn+0.135モルのCu+0.006モルのNi+0.006モルのPb+0.003モルのCdで置き換えた(=顔料AH)
実施例24:0.3モルのZnを0.015モルのZn+0.270モルのCu+0.015モルのFeで置き換えた(=顔料AI)
実施例25:0.3モルのZnを0.015モルのZn+0.270モルのCu+0.015モルのCdで置き換えた(=顔料AJ)
実施例26:0.3モルのZnを0.015モルのZn+0.270モルのCu+0.0075モルのNi+0.0075モルのCoで置き換えた(=顔料AK)
実施例27:0.3モルのZnを0.015モルのZn+0.270モルのCu+0.004モルのCr+0.006モルのPb+0.003モルのNiで置き換えた(=顔料AL)
実施例28:0.3モルのZnを0.273モルのZn+0.015モルのCu+0.012モルのNiで置き換えた(=顔料AM)
実施例29:0.3モルのZnを0.273モルのZn+0.015モルのCu+0.012モルのCoで置き換えた(=顔料AN)
実施例30:0.3モルのZnを0.273モルのZn+0.015モルのCu+0.004モルのCr+0.006モルのCdで置き換えた(=顔料AO)
実施例31:0.3モルのZnを0.273モルのZn+0.015モルのCu+0.0045モルのCd+0.0045モルのPb+0.003モルのFeで置き換えた(=顔料AP)
分散硬度は、25℃の冷間圧延温度および150℃の熱間圧延温度で、DIN 53 775,Part 7に従って測定する。本出願で報告される分散硬度は全て、この修正DIN法によって測定した。
製造された試験材料は、67.5%Vestolit(登録商標)E7004(Vestolit GmbH)、29.0%Hexamoll(登録商標)Dinch(BASF)、2.25%Baerostab UBZ 770(Baerlocher GmbH)および1.25%Isocolor白色顔料ペースト(ISL−Chemie)を実験室溶解機で均質化することによる、軟質PVC配合物であった。
X線回折法測定は、結晶相の識別に好適である、PIXcel検出器のPANalytical EMPYREANシータ/シータ反射回折計で行った。
表1に記載した実施例1〜28の試料を、次の通り分析した:
シータ/シータ測定値のそれぞれについて、試験されるべき量の試料を試料ホルダーの収納部へ導入した。試料の表面を、スクレーパーを用いて滑らかにした。
Claims (17)
- 金属アゾ顔料であって、以下の成分:
a)金属の種類の点で少なくとも異なり、そしてそれぞれ
・ 式(I)
R1およびR2はそれぞれ独立して、OH、NH2またはNHR5であり、
R3およびR4はそれぞれ独立して、=Oまたは=NR5であり、
R5は、水素またはアルキルである)
の構造単位、またはそれらの互変異性型
ならびに
・ Zn2+ およびCu2+金属イオンならびに任意選択により場合によっては少なくとも1つのさらなる金属イオンMe
(ここで、Meは、Ni 2+ 、Al 3+ 、Fe 2+ 、Fe 3+ 、Co 2+ 、Co 3+ 、La 3+ 、Ce 3+ 、Pr 3+ 、Nd 2+ 、Nd 3+ 、Sm 2+ 、Sm 3+ 、Eu 2+ 、Eu 3+ 、Gd 3+ 、Tb 3+ 、Dy 3+ 、Ho 3+ 、Yb 2+ 、Yb 3+ 、Er 3+ 、Tm 3+ 、Mg 2+ 、Ca 2+ 、Sr 2+ 、Mn 2+ 、Y 3+ 、Sc 3+ 、Ti 2+ 、Ti 3+ 、Nb 3+ 、Mo 2+ 、Mo 3+ 、V 2+ 、V 3+ 、Zr 2+ 、Zr 3+ 、Cd 2+ 、Cr 3+ 、Pb 2+ 、及びBa 2+ の群から選択される二価もしくは三価の金属イオンであり、
ただし、いずれの場合にもZn2+およびCu2+金属イオンを一緒にした量は、95〜100%であり、Al 3+ 、Fe 2+ 、Fe 3+ 、Co 2+ 、Co 3+ 、La 3+ 、Ce 3+ 、Pr 3+ 、Nd 2+ 、Nd 3+ 、Sm 2+ 、Sm 3+ 、Eu 2+ 、Eu 3+ 、Gd 3+ 、Tb 3+ 、Dy 3+ 、Ho 3+ 、Yb 2+ 、Yb 3+ 、Er 3+ 、Tm 3+ 、Mg 2+ 、Ca 2+ 、Sr 2+ 、Mn 2+ 、Y 3+ 、Sc 3+ 、Ti 2+ 、Ti 3+ 、Nb 3+ 、Mo 2+ 、Mo 3+ 、V 2+ 、V 3+ 、Zr 2+ 、Zr 3+ 、Cd 2+ 、Cr 3+ 、Pb 2+ 、及びBa 2+ の群から選択される金属イオンMeの量は、0〜5%であり、また、MeがNi 2+ である場合は、Zn 2+ およびCu 2+ 金属イオンを一緒にした量は98〜100%であり、Ni 2+ の量は0〜2%であり、
ここでこれらの金属イオンの量は、以下の式:(その金属イオンのモル量にその金属イオンの価数を乗じた値)÷(Zn 2+ 、Cu 2+ 、及びMeの全ての金属イオンについて、前記の金属イオンのモル量にその金属イオンの価数を乗じた値を合計した値)によって得られる値に基づく、金属アゾ顔料中に含まれる全ての金属イオンの値の合計を100%として計算される量であり、
そして
ここで、前記金属アゾ顔料中のZn2+対Cu2+金属イオンの前記式で計算される値の比は、199:1〜1:15である)
を含有する少なくとも2つの金属アゾ化合物と、
b)式(II)
R6は、水素またはアルキル(アルキルはOHによって任意選択によりモノもしくは多置換されていてもよい)である)
の少なくとも1つの化合物と
を含むことを特徴とする、金属アゾ顔料。 - 成分a)および成分b)が付加体の形態で一緒に存在することを特徴とする、請求項1に記載の金属アゾ顔料。
- 式(I)において、
R1およびR2がOHであり、
R3およびR4が=Oであり、
そして、式(II)において、
R6が水素である
ことを特徴とする、請求項1または2に記載の金属アゾ顔料。 - Meが、Al3+、Fe2+、Fe3+、Co2+、Co3+、La3+、Ce3+、Pr3+、Nd3+、Sm3+、Eu3+、Gd3+、Tb3+、Dy3+、Ho3+、Yb3+、Er3+、Tm3+、Mg2+、Ca2+、Sr2+、Mn2+、及びY3+の群からの金属イオンであることを特徴とする、請求項1〜3のいずれか一項に記載の金属アゾ顔料。
- Cu2+およびZn2+金属イオンを一緒にした量が、全金属イオンの量の合計を基準として、100%であることを特徴とする、請求項1〜4のいずれか一項に記載の金属アゾ顔料。
- 0.05〜4モルの式(II)の化合物が、式(I)の構造単位の1モル当たりに存在することを特徴とする、請求項1〜5のいずれか一項に記載の金属アゾ顔料。
- 20〜200m2/gの比表面積を有することを特徴とする、請求項1〜6のいずれか一項に記載の金属アゾ顔料。
- X線回折スペクトルにおいて、d=14.7(±0.3)Å〜d=11.8(±0.3)Åの面間間隔の間で、バックグラウンド値をこの値の平方根の3倍超える強度Iを有する少なくとも1つのシグナルSを有することを特徴とする、請求項1〜7のいずれか一項に記載の金属アゾ顔料。
- 請求項1〜8のいずれか一項に記載の金属アゾ顔料の製造方法であって、
式(III)
Xは、アルカリ金属イオンであり、
R1およびR2はそれぞれ独立して、OH、NH2またはNHR5であり、
R3およびR4はそれぞれ独立して、=Oまたは=NR5であり、
R5は、水素またはアルキルである)
の化合物、またはその互変異性体を、
式(II)
R6は、水素またはアルキル(アルキルはOHによって任意選択によりモノもしくは多置換されていてもよい)
の少なくとも1つの化合物の存在下で、
少なくとも1つの亜鉛塩および少なくとも1つの銅塩と、ならびに任意選択により場合によっては亜鉛および銅以外の二価もしくは三価の金属の少なくとも1つのさらなる金属塩とを、同時にもしくは順次反応させ、ここで、0.06〜0.995モルの少なくとも1つの亜鉛塩、0.005〜0.94モルの少なくとも1つの銅塩、ならびに0.05〜0モルの少なくとも1つのさらなる金属塩を式(III)の化合物1モル当たり使用し、そしてここで、これらの金属塩を一緒にしたモル量の合計が1モルであることを特徴とする、金属アゾ顔料の製造方法。 - 請求項1〜8のいずれか一項に記載の少なくとも1つの金属アゾ顔料と少なくとも1つの補助剤および/または添加剤と、任意選択により場合によっては少なくとも1つのさらなる顔料とを含む顔料調製物。
- C.I.Pigment Green 36および/またはC.I.Pigment Green 58をさらなる顔料として含むことを特徴とする、請求項10に記載の顔料調製物。
- 請求項1〜8のいずれか一項に記載の少なくとも1つの金属アゾ顔料が、少なくとも1つの補助剤および/または添加剤と、ならびに任意選択により場合によっては少なくとも1つのさらなる顔料と混合されるかまたはすり潰されることを特徴とする、請求項10又は11に記載の顔料調製物の製造方法。
- 顔料調製物の製造のための、請求項1〜8のいずれか一項に記載の金属アゾ顔料の使用。
- インクジェットインク、液晶ディスプレイ用のカラーフィルター、印刷インク、ディステンパーもしくはエマルジョンペイントを着色するための、合成、半合成もしくは天然の高分子物質の原料着色のための、および天然、再生もしくは合成繊維の紡糸染色のための、ならびに織物および紙の印刷のための、請求項1〜8のいずれか一項に記載の金属アゾ顔料の、または請求項10若しくは11に記載の顔料調製物の使用。
- 請求項1〜8のいずれか一項に記載の少なくとも1つの金属アゾ顔料、または請求項10若しくは11に記載の顔料調製物を含むカラーフィルター、フォトレジスト、印刷インクまたは液晶ディスプレイ。
- 請求項1〜8のいずれか一項に記載の少なくとも1つの金属アゾ顔料、または請求項10若しくは11に記載の顔料調製物と、1つもしくは複数の光硬化性モノマーと、1つもしくは複数の反応光開始剤と、任意選択により場合によっては1つもしくは複数のバインダーもしくは分散剤および/または溶媒とを含むフォトレジスト。
- 液晶ディスプレイ用のカラーフィルターの製造方法であって、完成した着色カラーフィルターを得るために、a)請求項16に記載のフォトレジストの基材への適用、b)フォトマスクを用いての露光、c)硬化、およびd)現像の工程を含む、製造方法。
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EP16161854.1A EP3222673A1 (de) | 2016-03-23 | 2016-03-23 | Metallazopigmente |
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JP7016879B2 (ja) * | 2017-10-20 | 2022-02-07 | 富士フイルム株式会社 | 着色組成物、膜の製造方法、カラーフィルタの製造方法、固体撮像素子の製造方法および画像表示装置の製造方法 |
WO2019107015A1 (ja) | 2017-11-29 | 2019-06-06 | 富士フイルム株式会社 | 組成物、膜、赤外線透過フィルタ、固体撮像素子および光センサ |
EP3979333A4 (en) | 2019-05-31 | 2022-08-17 | FUJIFILM Corporation | OPTICAL SENSOR AND DETECTION DEVICE |
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WO2022130773A1 (ja) | 2020-12-17 | 2022-06-23 | 富士フイルム株式会社 | 組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および赤外線センサ |
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DE19535246A1 (de) | 1995-09-22 | 1997-03-27 | Bayer Ag | Tensidgemische |
DE19712486A1 (de) | 1997-03-25 | 1998-10-01 | Bayer Ag | Verwendung von Pigmentpräparationen für den Ink-Jet Druck |
US6245138B1 (en) * | 1997-10-20 | 2001-06-12 | Bayer Aktiengesellschaft | Pigment preparations useful for ink-jet printing |
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DE19847586A1 (de) | 1998-10-15 | 2000-04-20 | Bayer Ag | Neue Pigmentformen |
ES2191393T3 (es) | 1998-10-15 | 2003-09-01 | Bayer Ag | Nuevos pigmentos de complejos metalicos. |
EP0994162B1 (de) | 1998-10-15 | 2004-01-14 | Bayer Chemicals AG | Metallkomplexpigmente |
ATE253619T1 (de) * | 2000-04-04 | 2003-11-15 | Bayer Ag | Organische pigmente für farbfilter in lcd |
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JP2017171914A (ja) | 2017-09-28 |
KR102323629B1 (ko) | 2021-11-08 |
TWI730069B (zh) | 2021-06-11 |
EP3222675B1 (de) | 2018-08-29 |
CN107227040A (zh) | 2017-10-03 |
EP3222675A1 (de) | 2017-09-27 |
EP3222673A1 (de) | 2017-09-27 |
US20170275468A1 (en) | 2017-09-28 |
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