JP4983029B2 - Coloring composition - Google Patents
Coloring composition Download PDFInfo
- Publication number
- JP4983029B2 JP4983029B2 JP2006026663A JP2006026663A JP4983029B2 JP 4983029 B2 JP4983029 B2 JP 4983029B2 JP 2006026663 A JP2006026663 A JP 2006026663A JP 2006026663 A JP2006026663 A JP 2006026663A JP 4983029 B2 JP4983029 B2 JP 4983029B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- phthalocyanine
- phthalocyanine pigment
- parts
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 238000004040 coloring Methods 0.000 title claims description 66
- 239000000203 mixture Substances 0.000 title claims description 63
- 239000000049 pigment Substances 0.000 claims description 171
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 88
- 229910052751 metal Inorganic materials 0.000 claims description 52
- 239000002184 metal Substances 0.000 claims description 52
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 30
- 239000011701 zinc Substances 0.000 claims description 30
- 229910052725 zinc Inorganic materials 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 26
- 239000011347 resin Substances 0.000 claims description 26
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical compound [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 claims description 20
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 15
- 239000010949 copper Substances 0.000 claims description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- 239000002243 precursor Substances 0.000 claims description 6
- -1 (Ni) Chemical class 0.000 description 27
- 239000000975 dye Substances 0.000 description 26
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000001055 blue pigment Substances 0.000 description 20
- 239000000976 ink Substances 0.000 description 20
- 150000004820 halides Chemical class 0.000 description 18
- 239000001056 green pigment Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000003860 storage Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- 239000006185 dispersion Substances 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000003973 paint Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 235000017168 chlorine Nutrition 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 6
- 229920000178 Acrylic resin Polymers 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229910017053 inorganic salt Inorganic materials 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical class [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000003021 water soluble solvent Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical class OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical class Br* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 125000005017 substituted alkenyl group Chemical group 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- 229940114072 12-hydroxystearic acid Drugs 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000002202 Polyethylene glycol Substances 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
- 125000003277 amino group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000001309 chloro group Chemical class Cl* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007645 offset printing Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- LRSLDYIFOCTRHR-UHFFFAOYSA-N (3-benzoyl-4-ethylphenyl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=C(CC)C(C(=O)C=2C=CC=CC=2)=C1 LRSLDYIFOCTRHR-UHFFFAOYSA-N 0.000 description 1
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
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- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Optical Filters (AREA)
Description
本発明は、フタロシアニン顔料を含む着色組成物に関するものであり、更に詳しくは、インキや塗料に有効な、フタロシアニン顔料を含む着色組成物に関するものである。 The present invention relates to a coloring composition containing a phthalocyanine pigment, and more particularly to a coloring composition containing a phthalocyanine pigment that is effective for inks and paints.
一般に、各種インキおよび塗料においては、鮮明な色調と広い色表示領域を持ち、高い着色力を発揮する色材が求められている。現在、オフセットインキ、グラビアインキおよび塗料には、フタロシアニン顔料が用いられているが、更なる色表示領域を広げることや、着色力を上げることは非常に困難である。
具体的には、緑色インキや塗料の色材としては、C.I. Pigment Green36、C.I. Pigment Green7等の銅フタロシアニングリーン顔料が用いられ、青色インキや塗料の色材としては、C.I. Pigment Blue15、15:1、15:2、15:3、15:4、15:6等の銅フタロシアニンブルー顔料が用いられている。
Generally, in various inks and paints, there is a demand for a color material having a clear color tone and a wide color display area and exhibiting high coloring power. At present, phthalocyanine pigments are used for offset inks, gravure inks and paints, but it is very difficult to further expand the color display area and increase the coloring power.
Specifically, copper phthalocyanine green pigments such as CI Pigment Green 36 and CI Pigment Green 7 are used as the color material for green ink and paint, and CI Pigment Blue 15, 15: 1, as the color material for blue ink and paint. Copper phthalocyanine blue pigments such as 15: 2, 15: 3, 15: 4, and 15: 6 are used.
鮮明な色調を得るために、顔料粒子は微細化し細かく整えられ、明暗のはっきりしたインキや塗料を得ることができる。
しかし、着色力および色表示領域は、顔料の化学構造に由来するもので、現在使用しているC.I. Pigment Green36、C.I. Pigment Green7、C.I. Pigment Blue15、15:1、15:2、15:3、15:4、15:6等の銅フタロシアニン顔料では、十分に満足すべきものには至らなかった（特許文献１、特許文献２を参照）。
However, the coloring power and the color display area are derived from the chemical structure of the pigment. CI Pigment Green 36, CI Pigment Green 7, CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15 However, copper phthalocyanine pigments such as: 4 and 15: 6 have not been fully satisfactory (see Patent Document 1 and Patent Document 2).
本発明の課題は、インキや塗料に用いた場合に、着色力が高く、かつ色表示領域が広い、良好な着色組成物を提供することにある。 An object of the present invention is to provide an excellent coloring composition having a high coloring power and a wide color display area when used in inks and paints.
本発明の着色組成物は、樹脂、その前駆体またはそれらの混合物からなる顔料担体と、中心金属としてアルミニウムを有するアルミニウムフタロシアニン顔料と、中心金属として亜鉛を有する亜鉛フタロシアニン顔料とを含むことを最も主要な特徴とする。 The coloring composition of the present invention is mainly composed of a pigment carrier comprising a resin, a precursor thereof or a mixture thereof, an aluminum phthalocyanine pigment having aluminum as a central metal, and a zinc phthalocyanine pigment having zinc as a central metal. Features.
本発明の着色組成物を用いることにより、鮮明な色調だけでなく、高い着色力、広い色表示領域を持った良好なインキ及び塗料を得ることができる。 By using the coloring composition of the present invention, it is possible to obtain a good ink and paint having not only a clear color tone but also a high coloring power and a wide color display area.
本発明の着色組成物は、樹脂、その前駆体またはそれらの混合物からなる顔料担体と、中心金属としてアルミニウムを有するアルミニウムフタロシアニン顔料と、中心金属として亜鉛を有する亜鉛フタロシアニン顔料とを含むものである。
アルミニウムフタロシアニン顔料は、鮮明な色調を発揮すると共に、広い色表示領域を発揮する。また、亜鉛フタロシアニン顔料は、広い色表示領域を発揮すると共に、高い着色力を発揮する。そのため、本発明の着色組成物は、鮮明な色調、広い色表示領域、高い着色力を満足する。
The coloring composition of the present invention comprises a pigment carrier made of a resin, a precursor thereof or a mixture thereof, an aluminum phthalocyanine pigment having aluminum as a central metal, and a zinc phthalocyanine pigment having zinc as a central metal.
Aluminum phthalocyanine pigments exhibit a clear color tone and a wide color display area. Moreover, the zinc phthalocyanine pigment exhibits a wide color display area and a high coloring power. Therefore, the coloring composition of the present invention satisfies a clear color tone, a wide color display area, and a high coloring power.
金属フタロシアニン顔料の合計重量を基準（１００重量％）とするアルミニウムフタロシアニン顔料の含有量は５〜４０重量％であることが好ましく、１０〜３０重量％であることがより好ましい。アルミニウムフタロシアニン顔料の含有量が５重量％未満の場合には、鮮明な色調と広い色表示領域を満足させることができず、４０重量％を超える場合には、着色力が低下し、保存安定性が悪くなる。 The content of the aluminum phthalocyanine pigment based on the total weight of the metal phthalocyanine pigment (100% by weight) is preferably 5 to 40% by weight, and more preferably 10 to 30% by weight. When the content of the aluminum phthalocyanine pigment is less than 5% by weight, a clear color tone and a wide color display area cannot be satisfied, and when it exceeds 40% by weight, the coloring power is lowered and the storage stability is reduced. Becomes worse.
また、金属フタロシアニン顔料の合計重量を基準（１００重量％）とする亜鉛フタロシアニン顔料の含有量は６０〜９５重量％であることが好ましく、７０〜９０重量％であることがより好ましい。亜鉛フタロシアニン顔料の含有量が６０重量％未満の場合には、着色力が低下し、広い色表示領域を満足させることができず、９５重量％を超える場合には、鮮明な色調でなくなり、保存安定性が悪くなる。
本発明の着色組成物は、さらに、中心金属としてアルミニウムおよび亜鉛以外の金属を有する異種金属フタロシアニン顔料を含むことができ、なかでも中心金属として銅を有する銅フタロシアニン顔料は、鮮明な色調を発揮するため、好ましい。
The content of the zinc phthalocyanine pigment based on the total weight of the metal phthalocyanine pigment (100% by weight) is preferably 60 to 95% by weight, and more preferably 70 to 90% by weight. When the content of the zinc phthalocyanine pigment is less than 60% by weight, the coloring power is lowered and the wide color display area cannot be satisfied. When the content exceeds 95% by weight, the clear color tone is lost and the color is not stored. Stability deteriorates.
The colored composition of the present invention can further include a dissimilar metal phthalocyanine pigment having a metal other than aluminum and zinc as a central metal, and a copper phthalocyanine pigment having copper as a central metal exhibits a clear color tone. Therefore, it is preferable.
また、顔料としてアルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料と銅フタロシアニン顔料の３種類の顔料のみを含む場合には、着色力、鮮明な色調、広い表示領域すべてを満足させ、さらに保存安定性に優れるため、より好ましい。この場合、アルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料との組み合わせだけでは困難であった保存安定性改良の点から、金属フタロシアニン顔料の合計重量を基準（１００重量％）とするアルミニウムフタロシアニン顔料の含有量は、好ましくは５〜４５重量％、より好ましくは１０〜４０重量％であり、亜鉛フタロシアニン顔料の含有量は、好ましくは３０〜８０重量％、より好ましくは４０〜７０重量％であり、銅フタロシアニン顔料の含有量は、好ましくは１０〜６０重量％、より好ましくは２０〜５０重量％である。 In addition, when only three types of pigments, aluminum phthalocyanine pigment, zinc phthalocyanine pigment and copper phthalocyanine pigment, are included as the pigment, coloring power, clear color tone, wide display area are all satisfied, and storage stability is excellent. More preferred. In this case, the content of the aluminum phthalocyanine pigment based on the total weight of the metal phthalocyanine pigment (100% by weight) from the viewpoint of improving the storage stability, which was difficult only by the combination of the aluminum phthalocyanine pigment and the zinc phthalocyanine pigment, The content of zinc phthalocyanine pigment is preferably 5 to 45% by weight, more preferably 10 to 40% by weight, and the content of zinc phthalocyanine pigment is preferably 30 to 80% by weight, more preferably 40 to 70% by weight. The content is preferably 10 to 60% by weight, more preferably 20 to 50% by weight.
本発明の着色組成物に用いられる金属フタロシアニン顔料は、下記一般式（１）で表されるフタロシアニン顔料である。
アルミニウムフタロシアニン顔料は、中心金属がアルミニウム（Ａｌ）のものである。また、亜鉛フタロシアニン顔料は、中心金属が亜鉛（Ｚｎ）のものである。他の中心金属としては、例えば、銅（Ｃｕ）、マグネシウム（Ｍｇ）、ケイ素（Ｓｉ）、チタン（Ｔｉ）、バナジウム（Ｖ）、マンガン（Ｍｎ）、鉄（Ｆｅ）、コバルト（Ｃｏ）、ニッケル（Ｎｉ）、ゲルマニウム（Ｇｅ）、スズ（Ｓｎ）等の各種金属が挙げられる。
The metal phthalocyanine pigment used in the coloring composition of the present invention is a phthalocyanine pigment represented by the following general formula (1).
The aluminum phthalocyanine pigment has a central metal of aluminum (Al). The zinc phthalocyanine pigment has a central metal of zinc (Zn). Other central metals include, for example, copper (Cu), magnesium (Mg), silicon (Si), titanium (Ti), vanadium (V), manganese (Mn), iron (Fe), cobalt (Co), nickel Various metals such as (Ni), germanium (Ge), tin (Sn), and the like can be given.
金属フタロシアニン顔料の中心金属は、銅、亜鉛、ニッケル等の二価金属、アルミニウム等の三価金属、ケイ素、チタン等の四価金属に分けられる。
中心金属が三価金属の場合には、中心金属は、１つのハロゲン原子、水酸基、スルホン酸基等の置換基を有する。また、中心金属が四価金属の場合には、中心金属は、１つの酸素原子、又は同一でも異なっていても良い２つのハロゲン原子、水酸基、スルホン酸基等の置換基を有する。
The central metal of the metal phthalocyanine pigment is classified into a bivalent metal such as copper, zinc and nickel, a trivalent metal such as aluminum, and a tetravalent metal such as silicon and titanium.
When the central metal is a trivalent metal, the central metal has one substituent such as a halogen atom, a hydroxyl group, and a sulfonic acid group. When the central metal is a tetravalent metal, the central metal has one oxygen atom or two substituents such as two halogen atoms, hydroxyl groups, and sulfonic acid groups that may be the same or different.
ハロゲン原子を有するフタロシアニン顔料としては、例えば、ハロゲン原子を有しない粗製フタロシアニンブルーを公知の方法でハロゲン化したのち、適切な粒子の大きさ（一次粒子径０．０５〜０．５μｍ）まで整粒（顔料化）したものを用いることができる。
粗製フタロシアニンブルーの中心金属は銅であるが、中心金属が銅以外の粗製フタロシアニンのハロゲン化も、粗製フタロシアニンブルーと同様の方法で行うことができる。
As a phthalocyanine pigment having a halogen atom, for example, a crude phthalocyanine blue having no halogen atom is halogenated by a known method, and then sized to an appropriate particle size (primary particle diameter of 0.05 to 0.5 μm). (Pigmented) can be used.
Although the central metal of crude phthalocyanine blue is copper, halogenation of crude phthalocyanine other than copper as the central metal can be carried out in the same manner as crude phthalocyanine blue.
金属フタロシアニン顔料は、微細化を行ってから用いてもよい。顔料の微細化は、例えば、下記の方法で行うことができる。
金属フタロシアニン顔料、水溶性の無機塩および水溶性の溶剤を含む混合物を粘土状にし、ニーダー等で強く練りこんで顔料を微細化したのち水中に投入し、ハイスピードミキサー等で攪拌してスラリー状とする。次いで、スラリーの濾過と水洗を繰り返して、水溶性の無機塩および水溶性の溶剤を除去する。顔料を微細化する工程においては、樹脂、顔料分散剤等を添加してもよい。水溶性の無機塩としては、塩化ナトリウム、塩化カリウム等が挙げられる。これらの無機塩は、金属フタロシアニン顔料の３重量倍以上、好ましくは２０重量倍以下の範囲で用いる。無機塩の量が３重量倍よりも少ないと、所望の大きさの微細化顔料が得られない。また、２０重量倍よりも多いと、後の工程における水溶性無機塩および水溶性溶剤の洗浄処理が多大であり、金属フタロシアニン顔料の実質的な微細化処理量が少なくなる。
The metal phthalocyanine pigment may be used after being refined. The refinement of the pigment can be performed, for example, by the following method.
A mixture containing a metal phthalocyanine pigment, a water-soluble inorganic salt and a water-soluble solvent is made into a clay, finely kneaded with a kneader, etc., then the pigment is refined, put into water, and stirred with a high-speed mixer or the like to form a slurry. And Next, filtration and washing of the slurry are repeated to remove the water-soluble inorganic salt and the water-soluble solvent. In the step of refining the pigment, a resin, a pigment dispersant or the like may be added. Examples of the water-soluble inorganic salt include sodium chloride and potassium chloride. These inorganic salts are used in the range of 3 times by weight or more, preferably 20 times by weight or less of the metal phthalocyanine pigment. If the amount of the inorganic salt is less than 3 times by weight, a refined pigment having a desired size cannot be obtained. On the other hand, when the amount is more than 20 times by weight, the washing treatment of the water-soluble inorganic salt and the water-soluble solvent in the subsequent step is enormous, and the substantial amount of the metal phthalocyanine pigment is reduced.
水溶性の溶剤は、金属フタロシアニン顔料と破砕助剤として用いられる水溶性の無機塩との適度な粘土状態をつくり、充分な破砕を効率よく行うために用いられる。水に溶解する溶剤であれば特に限定されないが、混練時に温度が上昇して溶剤が蒸発し易い状態になるため、安全性の点から沸点１２０〜２５０℃の高沸点の溶剤が好ましい。水溶性の溶剤としては、２−（メトキシメトキシ）エタノール、２−ブトキシエタノール、２−（イソペンチルオキシ）エタノール、２−（ヘキシルオキシ）エタノール、ジエチレングリコール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液体ポリエチレングリコール、１−メトキシ−２−プロパノール、１−エトキシ−２−プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、低分子量ポリプロピレングリコール等が挙げられる。 The water-soluble solvent is used for producing an appropriate clay state between the metal phthalocyanine pigment and a water-soluble inorganic salt used as a crushing aid, and performing sufficient crushing efficiently. Although it will not specifically limit if it is a solvent which melt | dissolves in water, Since the temperature rises at the time of kneading | mixing and it will be in the state which a solvent evaporates easily, a high boiling point solvent with a boiling point of 120-250 degreeC is preferable from a safety point. Examples of water-soluble solvents include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono Butyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low Examples thereof include molecular weight polypropylene glycol.
本発明の着色組成物は、さまざまな塗膜形成方法に対応し、分散性、耐熱性、耐候性、塗膜密着性等の諸特性を満足させるため、樹脂、その前駆体またはそれらの混合物からなる顔料担体を含む。樹脂としては、熱可塑性樹脂、熱硬化性樹脂、感光性樹脂を用いることができ、樹脂の前駆体としては、モノマー、オリゴマーを用いることができる。
熱可塑性樹脂としては、例えば、ブチラール樹脂、スチレンーマレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、ポリスチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリブタジエン、ポリエチレン、ポリプロピレン、ポリイミド樹脂等が挙げられる。また、熱硬化性樹脂としては、例えば、エポキシ樹脂、ベンゾグアナミン樹脂、ロジン変性マレイン酸樹脂、ロジン変性フマル酸樹脂、メラミン樹脂、尿素樹脂、フェノール樹脂等が挙げられる。
The coloring composition of the present invention is compatible with various coating film forming methods, and satisfies various properties such as dispersibility, heat resistance, weather resistance, coating film adhesion, etc., from a resin, its precursor or a mixture thereof. A pigment carrier. As the resin, a thermoplastic resin, a thermosetting resin, or a photosensitive resin can be used. As the precursor of the resin, a monomer or an oligomer can be used.
Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. And acrylic resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polybutadiene, polyethylene, polypropylene, polyimide resins, and the like. Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.
感光性樹脂としては、水酸基、カルボキシル基、アミノ基等の反応性の置換基を有する線状高分子に、イソシアネート基、アルデヒド基、エポキシ基等の反応性の置換基を有する（メタ）アクリル化合物やケイヒ酸を反応させて、（メタ）アクリロイル基、スチリル基等の光架橋性基を導入した樹脂が用いられる。また、スチレン−無水マレイン酸共重合体やα−オレフィン−無水マレイン酸共重合体等の酸無水物を含む線状高分子をヒドロキシアルキル（メタ）アクリレート等の水酸基を有する（メタ）アクリル化合物によりハーフエステル化したものも用いられる。 As a photosensitive resin, a (meth) acrylic compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group Or a resin in which a photocrosslinkable group such as a (meth) acryloyl group or a styryl group is introduced by reacting with or cinnamic acid is used. In addition, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified products are also used.
樹脂の前駆体であるモノマーおよびオリゴマーとしては、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、トリシクロデカニル（メタ）アクリレート、メラミン（メタ）アクリレート、エポキシ（メタ）アクリレート等の各種アクリル酸エステルおよびメタクリル酸エステル、（メタ）アクリル酸、スチレン、酢酸ビニル、（メタ）アクリルアミド、Ｎ−ヒドロキシメチル（メタ）アクリルアミド、アクリロニトリル等が挙げられる。 As monomers and oligomers that are precursors of the resin, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tri (meth) Acrylic esters such as acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, melamine (meth) acrylate, epoxy (meth) acrylate and the like, (meth) acrylic acid, styrene, Examples include vinyl acetate, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, acrylonitrile and the like.
本発明の着色組成物には、該組成物を紫外線照射により硬化するときには、光重合開始剤が添加される。光重合開始剤としては、４−フェノキシジクロロアセトフェノン、４−ｔ−ブチル−ジクロロアセトフェノン、ジエトキシアセトフェノン、１−（４−イソプロピルフェニル）−２−ヒドロキシ−２−メチルプロパン−１オン、１−ヒドロキシシクロヘキシルフェニルケトン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン等のアセトフェノン系光重合開始剤、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール等のベンゾイン系光重合開始剤、ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、４−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、４−ベンゾイル−４'−メチルジフェニルサルファイド等のベンゾフェノン系光重合開始剤、チオキサンソン、２−クロルチオキサンソン、２−メチルチオキサンソン、イソプロピルチオキサンソン、２，４−ジイソプロピルチオキサンソン等のチオキサンソン系光重合開始剤、２，４，６−トリクロロ−ｓ−トリアジン、２−フェニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−メトキシフェニル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（ｐ−トリル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−ピペロニル−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−ビス（トリクロロメチル）−６−スチリル−ｓ−トリアジン、２−（ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２−（４−メトキシ−ナフト−１−イル）−４，６−ビス（トリクロロメチル）−ｓ−トリアジン、２，４−トリクロロメチル−（ピペロニル）−６−トリアジン、２，４−トリクロロメチル（４'−メトキシスチリル）−６−トリアジン等のトリアジン系光重合開始剤、ボレート系光重合開始剤、カルバゾール系光重合開始剤、イミダゾール系光重合開始剤等が用いられる。
光重合開始剤は、着色組成物中の顔料の合計１００重量部に対して、５〜２００重量部、好ましくは１０〜１５０重量部の量で用いることができる。
When the composition is cured by ultraviolet irradiation, a photopolymerization initiator is added to the colored composition of the present invention. As photopolymerization initiators, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxy Acetophenone photopolymerization initiators such as cyclohexyl phenyl ketone and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether Benzoin photopolymerization initiators such as benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-ben Benzophenone photopolymerization initiators such as yl-4′-methyldiphenyl sulfide, thioxanthone light such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone Polymerization initiator, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloro) Methyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s-triazine, 2,4 -Bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (to Chloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine , 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine and other triazine photopolymerization initiators, borate photopolymerization initiators, carbazole photopolymerization initiators, imidazole photopolymerization initiators and the like are used. It is done.
A photoinitiator can be used in the amount of 5-200 weight part with respect to a total of 100 weight part of the pigment in a coloring composition, Preferably it is 10-150 weight part.
上記光重合開始剤は、単独あるいは２種以上混合して用いるが、増感剤として、α−アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、９，１０−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、４，４'−ジエチルイソフタロフェノン、３，３'，４，４'−テトラ（ｔ−ブチルパーオキシカルボニル）ベンゾフェノン、４，４'−ジエチルアミノベンゾフェノン等の化合物を併用することもできる。増感剤は、着色組成物中の光重合開始剤１００重量部に対して、０．１〜６０重量部の量で用いることができる。 The above photopolymerization initiators are used alone or in combination of two or more. As sensitizers, α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone. , Camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone, etc. It can also be used together. The sensitizer can be used in an amount of 0.1 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator in the colored composition.
本発明の着色組成物は、金属フタロシアニン顔料を、必要に応じて上記光重合開始剤と共に、顔料担体中に、三本ロールミル、二本ロールミル、サンドミル、ニーダー等の各種分散手段を用いて微細に分散して製造することができる。
金属フタロシアニン顔料を顔料担体中に分散する際には、適宜、樹脂型顔料分散剤、界面活性剤、色素誘導体等の分散助剤を含有させることができる。分散助剤は、顔料の分散に優れ、分散後の顔料の再凝集を防止する効果が大きいので、分散助剤を用いて顔料を顔料担体中に分散した場合には、分散性、特に保存安定性、低チキソ性に優れた着色組成物が得られる。分散助剤は、着色組成物中の顔料の合計１００重量部に対して、３〜２０重量部、好ましくは５〜１５重量部の量で用いることができる。
分散助剤のうち、塩基性基を有する色素誘導体、または酸性基を有する色素誘導体もしくはその塩は、顔料の分散効果が大きいため好適に用いられる。
In the coloring composition of the present invention, the metal phthalocyanine pigment is finely divided into various pigments such as a three-roll mill, a two-roll mill, a sand mill, and a kneader in the pigment carrier together with the photopolymerization initiator as necessary. It can be dispersed and manufactured.
When the metal phthalocyanine pigment is dispersed in the pigment carrier, a dispersion aid such as a resin-type pigment dispersant, a surfactant, or a pigment derivative can be appropriately contained. Dispersion aids are excellent in pigment dispersion and have a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, when a pigment is dispersed in a pigment carrier using a dispersion aid, dispersibility, especially storage stability is improved. And a colored composition excellent in low thixotropy can be obtained. The dispersion aid can be used in an amount of 3 to 20 parts by weight, preferably 5 to 15 parts by weight, based on 100 parts by weight of the total pigment in the coloring composition.
Among the dispersion aids, a dye derivative having a basic group, or a dye derivative having an acidic group or a salt thereof is preferably used because of a large pigment dispersion effect.
着色組成物に用いられる樹脂型分散剤は、酸性基または塩基性基をアンカーとして顔料の表面に吸着し、ポリマーの反発効果が有効に作用して分散安定性保持を発現することから、酸性基または塩基性基を有するポリマーであることが好ましい。酸性基としては、吸着特性に優れる点でスルホン基が好ましく、塩基性基としては、吸着特性に優れる点でアミノ基が好ましい。また、酸性基を有する色素誘導体と塩基性基を有する樹脂型分散剤との併用、または塩基性基を有する色素誘導体と酸性基を有する樹脂型分散剤との併用は、顔料担体との相性が良いため好ましい。 The resin-type dispersant used in the coloring composition is adsorbed on the surface of the pigment using an acidic group or a basic group as an anchor, and the repulsive effect of the polymer effectively acts to express dispersion stability. Or it is preferable that it is a polymer which has a basic group. The acidic group is preferably a sulfone group from the viewpoint of excellent adsorption characteristics, and the basic group is preferably an amino group from the viewpoint of excellent adsorption characteristics. Also, the combined use of a pigment derivative having an acidic group and a resin type dispersant having a basic group, or the combined use of a pigment derivative having a basic group and a resin type dispersant having an acidic group is compatible with the pigment carrier. It is preferable because it is good.
酸性基または塩基性基を有する樹脂型分散剤としては、酸性基または塩基性基を有する幹ポリマー部に枝ポリマー部がグラフト結合した構造の櫛型ポリマーが、枝ポリマー部の優れた立体反発効果から有機溶剤可溶性をより有するため好ましい。さらに、幹ポリマー１分子に２分子以上の枝ポリマーがグラフト結合した分子構造を有する櫛型ポリマーが上記理由からより好ましい。
塩基性樹脂型分散剤の具体例としては、ポリエチレンイミン、ポリエチレンポリアミン、ポリキシリレンポリ（ヒドロキシプロピレン）ポリアミン、ポリ（アミノメチル化）エポキシ樹脂、アミン付加グリシジル（メタ）アクリレート−（メタ）アクリル酸エステル化グリシジル（メタ）アクリレート共重合体等が挙げられる。これらの合成法は、例えば以下の通りである。
As a resin type dispersant having an acidic group or a basic group, a comb polymer having a structure in which a branch polymer part is graft-bonded to a trunk polymer part having an acidic group or a basic group has an excellent steric repulsion effect of the branch polymer part. It is preferable because it is more soluble in organic solvents. Furthermore, a comb polymer having a molecular structure in which two or more branch polymers are grafted to one molecule of the trunk polymer is more preferable for the above reason.
Specific examples of the basic resin type dispersant include polyethyleneimine, polyethylene polyamine, polyxylylene poly (hydroxypropylene) polyamine, poly (aminomethylated) epoxy resin, amine-added glycidyl (meth) acrylate- (meth) acrylic acid Examples include esterified glycidyl (meth) acrylate copolymers. These synthesis methods are as follows, for example.
ポリエチレンイミンは、エチレンイミンを酸触媒存在下で開環重合することで得られる。
ポリエチレンポリアミンは、二塩化エチレンとアンモニアをアルカリ触媒存在下で重縮合することで得られる。
ポリ（アミノメチル化）エポキシ樹脂は、ビスフェノールＡ型エポキシ樹脂、ビスフェノールＦ型エポキシ樹脂、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、ナフトールノボラック型エポキシ樹脂等の芳香環をクロルメチル化後にアミノ化することで得られ、別名マンニッヒ塩基と呼ばれる。アミノ化で使用するアミンとして具体的には、モノメチルアミン、モノエチルアミン、モノメタノールアミン、モノエタノールアミン、ジメチルアミン、ジエチルアミン、ジメタノールアミン、ジエタノールアミン等が挙げられる。
Polyethyleneimine is obtained by ring-opening polymerization of ethyleneimine in the presence of an acid catalyst.
Polyethylene polyamine can be obtained by polycondensation of ethylene dichloride and ammonia in the presence of an alkali catalyst.
Poly (aminomethylated) epoxy resin aminates aromatic rings such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, cresol novolac type epoxy resin, naphthol novolak type epoxy resin after chloromethylation And is also called Mannich base. Specific examples of the amine used in the amination include monomethylamine, monoethylamine, monomethanolamine, monoethanolamine, dimethylamine, diethylamine, dimethanolamine, diethanolamine and the like.
アミン付加グリシジル（メタ）アクリレート−（メタ）アクリル酸エステル化グリシジル（メタ）アクリレート共重合体は、グリシジル（メタ）アクリレートをラジカル重合してポリマー化した後、同ポリマー中のエポキシ基の一部に先に例示したものと同様のアミンを付加してポリ〔アミン付加グリシジル（メタ）アクリレート〕を得た後、残ったエポキシ基を（メタ）アクリル酸のカルボン酸とエステル化反応させて得られる。 The amine-added glycidyl (meth) acrylate- (meth) acrylic esterified glycidyl (meth) acrylate copolymer is polymerized by radical polymerization of glycidyl (meth) acrylate, and then a part of the epoxy group in the polymer. An amine similar to that exemplified above is added to obtain poly [amine-added glycidyl (meth) acrylate], and then the remaining epoxy group is obtained by esterification with a carboxylic acid of (meth) acrylic acid.
枝ポリマーは、有機溶剤可溶性のものが好ましく、その具体例としては、ポリマー末端にカルボン酸を有し、前記したような幹ポリマーのアミノ基とアミド化反応することでグラフト結合を形成し得るポリマーであるポリ（１２−ヒドロキシステアリン酸）、ポリリシノール酸、ε−カプロラクトン等の開環重合体等が挙げられる。また、幹ポリマーが前記したアミン付加グリシジル（メタ）アクリレート−（メタ）アクリル酸エステル化グリシジル（メタ）アクリレート共重合体のようにビニル基を有する場合には、該ビニル基にグラフト重合し得るポリ〔（メタ）アクリル酸メチル〕、ポリ〔（メタ）アクリル酸エチル〕等を枝ポリマーとして挙げることができる。これらの合成法は例えば以下の通りである。 The branched polymer is preferably an organic solvent-soluble polymer. Specific examples thereof include a polymer having a carboxylic acid at the polymer terminal and capable of forming a graft bond by amidation with the amino group of the trunk polymer as described above. And ring-opening polymers such as poly (12-hydroxystearic acid), polyricinoleic acid, and ε-caprolactone. Further, when the backbone polymer has a vinyl group such as the above-mentioned amine-added glycidyl (meth) acrylate- (meth) acrylate esterified glycidyl (meth) acrylate copolymer, a polypolymer that can be graft-polymerized to the vinyl group. [Methyl (meth) acrylate], poly [(meth) ethyl acrylate] and the like can be listed as the branch polymer. These synthesis methods are as follows, for example.
ポリ（１２−ヒドロキシステアリン酸）は、１２−ヒドロキシステアリン酸の脱水重縮合ポリエステル化反応によって得られる。
ポリリシノール酸は、同様にリシノール酸の脱水重縮合ポリエステル化反応によって得られる。
ε−カプロラクトンの開環重合体は、ε−カプロラクトンに脂肪族モノカルボン酸であるｎ−カプロン酸を付加させて開環重合を開始させて得られる。
Poly (12-hydroxystearic acid) is obtained by a dehydration polycondensation polyesterification reaction of 12-hydroxystearic acid.
Polyricinoleic acid is similarly obtained by a dehydration polycondensation polyesterification reaction of ricinoleic acid.
A ring-opening polymer of ε-caprolactone is obtained by adding n-caproic acid, which is an aliphatic monocarboxylic acid, to ε-caprolactone to initiate ring-opening polymerization.
界面活性剤は、顔料の分散を向上させるだけでなく、塗布時の着色組成物の表面張力をコントロールし、均一な乾燥塗膜が得られるようにする効果も有する。界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどのアニオン性界面活性剤；ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレートなどのノニオン性界面活性剤；アルキル４級アンモニウム塩やそれらのエチレンオキサイド付加物などのカオチン性界面活性剤；アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤が挙げられ、これらは単独でまたは２種以上を混合して用いることができる。 The surfactant not only improves the dispersion of the pigment, but also has an effect of controlling the surface tension of the colored composition at the time of coating so that a uniform dry coating film can be obtained. Surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, lauryl sulfate monoethanolamine, lauryl Anionic surfactants such as triethanolamine sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more.
色素誘導体は、有機色素に塩基性基または酸性基を導入した化合物である。有機色素には、一般に色素とは呼ばれていないナフタレン系、アントラキノン系等の淡黄色の芳香族多環化合物やトリアジンも含まれる。色素誘導体としては、特開昭６３−３０５１７３号公報、特公昭５７−１５６２０号公報、特公昭５９−４０１７２号公報、特公昭６３−１７１０２号公報、特公平５−９４６９号公報等に記載されているものを使用できる。なかでも、塩基性基を有する色素誘導体は、顔料の分散効果が大きいため、好適に用いられる。 A dye derivative is a compound in which a basic group or an acidic group is introduced into an organic dye. Organic dyes include naphthalene-based and anthraquinone-based light yellow aromatic polycyclic compounds and triazines that are not generally called dyes. Examples of the dye derivatives are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. You can use what you have. Especially, since the pigment | dye derivative which has a basic group has a large pigment dispersion effect, it is used suitably.
色素誘導体を構成する有機色素としては、例えば、ジケトピロロピロール系色素、アゾ、ジスアゾ、ポリアゾ等のアゾ系色素、フタロシアニン系色素、ジアミノジアントラキノン、アントラピリミジン、フラバントロン、アントアントロン、インダントロン、ピラントロン、ビオラントロン等のアントラキノン系色素、キナクリドン系色素、ジオキサジン系色素、ペリノン系色素、ペリレン系色素、チオインジゴ系色素、イソインドリン系色素、イソインドリノン系色素、キノフタロン系色素、スレン系色素、金属錯体系色素が挙げられる。また、先に例示した有機顔料でもよい。 Examples of the organic dye constituting the dye derivative include, for example, diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, Anthraquinone dyes such as pyranthrone, violanthrone, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes, metal complexes Systematic dyes. Moreover, the organic pigment illustrated previously may be sufficient.
色素誘導体が有する塩基性基として具体的には、下記一般式２、３、４および５で表される置換基が挙げられる。なかでも、下記一般式５で表されるトリアジン環含有の塩基性基を有する色素誘導体は、顔料の分散効果が大きいため、好適である。
一般式２
General formula 2
上記式２〜５において、Ｘは、−ＳＯ2−、−ＣＯ−、−ＣＨ2ＮＨＣＯＣＨ2−、−ＣＨ2−または直接結合を表す。
ｎは、１〜１０の整数を表し、好ましくは１〜３の整数である。
Ｒ1およびＲ2は、それぞれ独立に、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基もしくは置換されていてもよいフェニル基を表すか、またはＲ1とＲ2とが結合して更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を形成する。Ａ1およびＡ2は、好ましくは、１〜５個の炭素原子を有する非置換もしくは置換アルキル基である。
Ｒ3は、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。Ｒ3は、好ましくは、１〜４個の炭素原子を有する非置換もしくは置換アルキル基である。
In the above formulas 2 to 5, X represents —SO 2 —, —CO—, —CH 2 NHCOCH 2 —, —CH 2 — or a direct bond.
n represents an integer of 1 to 10, preferably an integer of 1 to 3.
R 1 and R 2 each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Or R 1 and R 2 combine to form an optionally substituted heterocycle containing additional nitrogen, oxygen or sulfur atoms. A 1 and A 2 are preferably unsubstituted or substituted alkyl groups having 1 to 5 carbon atoms.
R 3 represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. R 3 is preferably an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms.
Ｒ4、Ｒ5、Ｒ6およびＲ7は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。Ｒ4、Ｒ5、Ｒ6およびＲ7は、好ましくは、１〜４個の炭素原子を有する非置換もしくは置換アルキル基である。
Ｙは、−ＮＲ8−Ｚ−ＮＲ9−または直接結合を表す。
Ｒ8およびＲ9は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基または置換されていてもよいフェニル基を表す。Ｒ8およびＲ9は、好ましくは、それぞれ、水素原子である。
R 4 , R 5 , R 6 and R 7 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or Represents an optionally substituted phenyl group. R 4 , R 5 , R 6 and R 7 are preferably unsubstituted or substituted alkyl groups having 1 to 4 carbon atoms.
Y represents —NR 8 —Z—NR 9 — or a direct bond.
R 8 and R 9 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted group. Represents a phenyl group. R 8 and R 9 are preferably each a hydrogen atom.
Ｚは、炭素数１〜３６の置換されていてもよいアルキレン基、炭素数２〜３６の置換されていてもよいアルケニレン基、または置換されていてもよいフェニレン基を表す。Ｚは、好ましくは、非置換もしくは置換フェニレン基である。
Ｐは、下記式６で示される置換基または下記式７で示される置換基を表す。下記式６および７において、Ｒ1〜Ｒ7、およびｎは、上に定義したとおりである。
Ｑは、水酸基、アルコキシル基、下記式６で示される置換基または下記式７で示される置換基を表す。Ｑは、好ましくは、下記式６で示される置換基である。
Z represents an alkylene group having 1 to 36 carbon atoms which may be substituted, an alkenylene group having 2 to 36 carbon atoms which may be substituted, or a phenylene group which may be substituted. Z is preferably an unsubstituted or substituted phenylene group.
P represents a substituent represented by the following formula 6 or a substituent represented by the following formula 7. In the following formulas 6 and 7, R 1 to R 7 and n are as defined above.
Q represents a hydroxyl group, an alkoxyl group, a substituent represented by the following formula 6 or a substituent represented by the following formula 7. Q is preferably a substituent represented by the following formula 6.
一般式６
塩基性基を有する色素誘導体は、種々の合成経路で合成することができる。例えば、有機色素に、下記式８〜１１で表される置換基を導入した後、該置換基と反応して一般式２〜５で表される置換基を形成するアミン成分、例えば、Ｎ，Ｎ−ジメチルアミノプロピルアミン、Ｎ−メチルピペラジン、ジエチルアミンまたは４−［４−ヒドロキシ−６−［３−（ジブチルアミノ）プロピルアミノ］−１，３，５−トリアジン−２−イルアミノ］アニリン等を反応させることによって得られる。 A pigment derivative having a basic group can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the following formulas 8 to 11 into an organic dye, an amine component that reacts with the substituent to form a substituent represented by the general formula 2 to 5, such as N, Reaction with N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazin-2-ylamino] aniline, etc. To obtain.
式８ −ＳＯ2Ｃｌ
式９ −ＣＯＣｌ
式１０ −ＣＨ2ＮＨＣＯＣＨ2Ｃｌ
式１１ −ＣＨ2Ｃｌ
Formula 8 —SO 2 Cl
Formula 9 -COCl
Formula 10 —CH 2 NHCOCH 2 Cl
Formula 11 —CH 2 Cl
また、色素誘導体が有する酸性基としては、スルホン酸基等が挙げられる。スルホン酸基を有する色素誘導体は、有機顔料に硫酸を作用させることで製造することができる。スルホン酸基は、リチウム、カリウム、ナトリウム、カルシウム、マグネシウム、ストロンチウム、アルミニウムなどの１〜３価の金属原子、エチルアミン、ブチルアミン等のモノアルキルアミン、ジメチルアミン、ジエチルアミン等のジアルキルアミン、トリメチルアミン、トリエチルアミン等のトリアルキルアミン、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のアルカノールアミン等の有機アミン、アンモニアなどと塩を形成していても良い。
色素誘導体としては、表１〜１３に示すものを用いることができるが、これらに限定されるわけではない。色素誘導体は、単独でまたは２種類以上を混合して用いることができる。
Examples of the acidic group that the pigment derivative has include a sulfonic acid group. A dye derivative having a sulfonic acid group can be produced by allowing sulfuric acid to act on an organic pigment. Sulfonic acid groups include 1 to 3 metal atoms such as lithium, potassium, sodium, calcium, magnesium, strontium, and aluminum, monoalkylamines such as ethylamine and butylamine, dialkylamines such as dimethylamine and diethylamine, trimethylamine, and triethylamine. A salt may be formed with an organic amine such as alkanolamine such as trialkylamine, monoethanolamine, diethanolamine or triethanolamine, ammonia or the like.
As the pigment derivative, those shown in Tables 1 to 13 can be used, but are not limited thereto. The pigment derivatives can be used alone or in admixture of two or more.
また、本発明の着色組成物には、上記金属フタロシアニン顔料に加えて、他の顔料を含有させて色相をコントロールすることができる。
緑色着色組成物の場合には、例えば、C.I. Pigment Yellow １、２、３、４、５、６、１０、１２、１３、１４、１５、１６、１７、１８、２４、３１、３２、３４、３５、３５：１、３６、３６：１、３７、３７：１、４０、４２、４３、５３、５５、６０、６１、６２、６３、６５、７３、７４、７７、８１、８３、９３、９４、９５、９７、９８、１００、１０１、１０４、１０６、１０８、１０９、１１０、１１３、１１４、１１５、１１６、１１７、１１８、１１９、１２０、１２３、１２６、１２７、１２８、１２９、１３８、１３９、１４７、１５０、１５１、１５２、１５３、１５４、１５５、１５６、１６１、１６２、１６４、１６６、１６７、１６８、１６９、１７０、１７１、１７２、１７３、１７４、１７５、１７６、１７７、１７９、１８０、１８１、１８２、１８５、１８７、１８８、１９３、１９４、１９８、１９９、２１３、２１４等の黄色顔料を併用することができる。
青色着色組成物の場合には、例えば、C.I. Pigment Violet１、１９、２３、２７、３２、４２、８０等の紫色顔料を併用することができる。
Moreover, in addition to the said metal phthalocyanine pigment, the coloring composition of this invention can contain another pigment, and a hue can be controlled.
In the case of a green coloring composition, for example, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 17 , It can be used in combination with the yellow pigments such as 179,180,181,182,185,187,188,193,194,198,199,213,214.
In the case of a blue coloring composition, purple pigments such as CI Pigment Violet 1, 19, 23, 27, 32, 42, 80 can be used in combination.
着色組成物には、顔料を充分に顔料担体中に分散させ、ガラス基板、プラスチック基板等の基材に対する塗布を容易にするために、溶剤を含有させることができる。溶剤としては、例えばシクロヘキサノン、エチルセロソルブアセテート、ブチルセロソルブアセテート、１−メトキシ−２−プロピルアセテート、ジエチレングリコールジメチルエーテル、エチルベンゼン、エチレングリコールジエチルエーテル、キシレン、エチルセロソルブ、メチル−ｎ−アミルケトン、プロピレングリコールモノメチルエーテル、トルエン、メチルエチルケトン、酢酸エチル、メタノール、エタノール、イソプロピルアルコール、ブタノール、イソブチルケトン、石油系溶剤等が挙げられ、これらを単独でもしくは混合して用いる。
溶剤は、着色組成物中の顔料の合計１００重量部に対して、８００〜４０００重量部、好ましくは１０００〜２５００重量部の量で用いることができる。
The coloring composition may contain a solvent in order to sufficiently disperse the pigment in the pigment carrier and facilitate application to a base material such as a glass substrate or a plastic substrate. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n-amyl ketone, propylene glycol monomethyl ether, toluene , Methyl ethyl ketone, ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent, and the like. These may be used alone or in combination.
The solvent can be used in an amount of 800 to 4000 parts by weight, preferably 1000 to 2500 parts by weight, based on 100 parts by weight of the total pigment in the coloring composition.
また、本発明の着色組成物には、着色組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。貯蔵安定剤としては、例えばベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの４級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、ｔ−ブチルピロカテコール、テトラエチルホスフィン、テトラフェニルフォスフィンなどの有機ホスフィン、亜リン酸塩等が挙げられる。
貯蔵安定剤は、着色組成物中の顔料の合計１００重量部に対して、０．１〜１０重量部の量で用いることができる。
In addition, the colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the colored composition. Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Examples thereof include phosphine and phosphite.
A storage stabilizer can be used in the quantity of 0.1-10 weight part with respect to a total of 100 weight part of the pigment in a coloring composition.
本発明の着色組成物は、遠心分離、焼結フィルタ、メンブレンフィルタ等の手段にて、５μｍ以上の粗大粒子、好ましくは１μｍ以上の粗大粒子、さらに好ましくは０．５μｍ以上の粒子および混入した塵の除去を行うことが好ましい。
本発明の着色組成物は、グラビアオフセット用印刷インキ、水無しオフセット用印刷インキ、シルクスクリーン印刷用インキ、インクジェットインキ、溶剤現像型あるいはアルカリ現像型着色レジスト材の形態で調製することができる。着色レジスト材は、熱硬化性樹脂または熱可塑性樹脂とモノマー、光重合開始剤を含有する組成物中に、顔料と、顔料分散剤とを分散させたものである。
The colored composition of the present invention can be obtained by means of centrifugal separation, sintering filter, membrane filter or the like, coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably particles of 0.5 μm or more and mixed dust. Is preferably removed.
The coloring composition of the present invention can be prepared in the form of gravure offset printing ink, waterless offset printing ink, silk screen printing ink, inkjet ink, solvent development type or alkali development type colored resist material. The colored resist material is obtained by dispersing a pigment and a pigment dispersant in a composition containing a thermosetting resin or a thermoplastic resin, a monomer, and a photopolymerization initiator.
以下に、本発明を実施例に基づいて説明するが、本発明はこれによって限定されるものではない。なお、実施例および比較例中、「部」とは「重量部」を意味する。
まず、実施例および比較例で用いた樹脂溶液および顔料について説明する。
Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “parts” means “parts by weight”.
First, resin solutions and pigments used in Examples and Comparative Examples will be described.
（アクリル樹脂溶液の調製）
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けた反応容器にシクロヘキサノン７０．０部を仕込み、８０℃に昇温し、反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート１３．３部、２−ヒドロキシエチルメタクリレート４．６部、メタクリル酸４．３部、パラクミルフェノールエチレンオキサイド変性アクリレート（東亞合成株式会社製「アロニックスＭ１１０」）７．４部、２，２'−アゾビスイソブチロニトリル０．４部の混合物を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、重量平均分子量２６０００のアクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約２ｇをサンプリングして１８０℃、２０分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が２０重量％になるようにシクロヘキサノンを添加してアクリル樹脂溶液を調製した。
(Preparation of acrylic resin solution)
A reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, and a stirrer was charged with 70.0 parts of cyclohexanone, heated to 80 ° C., and the inside of the reaction vessel was purged with nitrogen. 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), A mixture of 0.4 part of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain an acrylic resin solution having a weight average molecular weight of 26000. After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% by weight. To prepare an acrylic resin solution.
以下に、粗製緑色顔料の合成法を記す。なお、合成した粗製顔料中の金属の測定は、以下の方法で行った。まず、１００ｍｌビーカーに粗製顔料０．５ｇ、硫酸１ｍｌ，および硝酸３ｍｌを入れ、ガスコンロで１時間３０分加熱して分解後、６００℃の電気炉で４時間加熱して分解した。分解物に、塩酸５ｍｌおよび純水２５ｍｌ入れて溶解し、溶解物を５０ｍｌに定容し、ＩＣＰ原子発光分光分析により金属原子量を測定した。また、粗製顔料中の塩素、臭素の数（１分子内に含まれる平均塩素数および平均臭素数）は、Ｎｏ．６の濾紙に粗製顔料０．０１ｇを包み、過酸化水素５滴を滴下して、酸素置換した燃焼フラスコ中で燃焼した。燃焼後１００ｍｌに定容し、イオンクロマトグラフ分析により測定した。 Below, the synthesis method of a crude green pigment is described. In addition, the measurement of the metal in the synthetic | combination crude pigment was performed with the following method. First, 0.5 g of crude pigment, 1 ml of sulfuric acid, and 3 ml of nitric acid were placed in a 100 ml beaker, decomposed by heating for 1 hour 30 minutes on a gas stove, and then heated for 4 hours in a 600 ° C. electric furnace for decomposition. The decomposition product was dissolved in 5 ml of hydrochloric acid and 25 ml of pure water, and the dissolution product was made up to a volume of 50 ml, and the amount of metal atoms was measured by ICP atomic emission spectrometry. The number of chlorine and bromine in the crude pigment (average number of chlorines and average number of bromines contained in one molecule) The filter paper of No. 6 was wrapped with 0.01 g of crude pigment, 5 drops of hydrogen peroxide were added dropwise, and burned in a combustion flask purged with oxygen. After combustion, the volume was fixed to 100 ml and measured by ion chromatography analysis.
（粗製ハロゲン化銅フタロシアニン顔料の合成）
塩化アルミニウム３５６部および塩化ナトリウム６部の２００℃の溶融塩に、銅フタロシアニン４６部を溶解し、１３０℃まで冷却し１時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり１０部で１０時間滴下した。その後、塩素を１時間あたり０．８部で５時間導入した。この反応液を水３２００部に徐々に注入したのち、濾過、水洗して１２０．２部の粗製ハロゲン化銅フタロシアニン顔料を得た。粗製ハロゲン化銅フタロシアニン顔料の１分子内に含まれる平均臭素数は１３．５個、平均塩素数は２．５個であった。
(Synthesis of crude copper halide phthalocyanine pigment)
In a molten salt of 356 parts of aluminum chloride and 6 parts of sodium chloride at 200 ° C., 46 parts of copper phthalocyanine was dissolved, cooled to 130 ° C. and stirred for 1 hour. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 10 parts per hour for 10 hours. Thereafter, chlorine was introduced at 0.8 parts per hour for 5 hours. The reaction mixture was gradually poured into 3200 parts of water, then filtered and washed with water to obtain 120.2 parts of a crude copper halide phthalocyanine pigment. The average number of bromines contained in one molecule of the crude copper halide phthalocyanine pigment was 13.5, and the average number of chlorines was 2.5.
（粗製ハロゲン化アルミニウムフタロシアニン顔料の合成）
塩化アルミニウム３５６部および塩化ナトリウム６部の２００℃の溶融塩に、アルミニウムフタロシアニン４６部を溶解し、１３０℃まで冷却し１時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり１０部で１０時間滴下した。その後、塩素を１時間あたり０．８部で５時間導入した。この反応液を水３２００部に徐々に注入したのち、濾過、水洗して１１０．８部の粗製ハロゲン化アルミニウムフタロシアニン顔料を得た。粗製ハロゲン化アルミニウムフタロシアニン顔料の１分子内に含まれる平均臭素数は１４．０個、平均塩素数は２．０個であった。
(Synthesis of crude aluminum halide phthalocyanine pigment)
In 200 ° C molten salt of 356 parts of aluminum chloride and 6 parts of sodium chloride, 46 parts of aluminum phthalocyanine was dissolved, cooled to 130 ° C, and stirred for 1 hour. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 10 parts per hour for 10 hours. Thereafter, chlorine was introduced at 0.8 parts per hour for 5 hours. The reaction solution was gradually poured into 3200 parts of water, then filtered and washed with water to obtain 110.8 parts of a crude aluminum halide phthalocyanine pigment. The average number of bromines contained in one molecule of the crude aluminum halide phthalocyanine pigment was 14.0, and the average number of chlorines was 2.0.
（粗製ハロゲン化亜鉛フタロシアニン顔料の合成）
塩化アルミニウム３５６部および塩化ナトリウム６部の２００℃の溶融塩に、亜鉛フタロシアニン４６部を溶解し、１３０℃まで冷却し１時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり１０部で１０時間滴下した。その後、塩素を１時間あたり０．８部で５時間導入した。この反応液を水３２００部に徐々に注入したのち、濾過、水洗して１０７．８部の粗製ハロゲン化亜鉛フタロシアニン顔料を得た。粗製ハロゲン化亜鉛フタロシアニン顔料の１分子内に含まれる平均臭素数は１４．１個、平均塩素数は１．９個であった。
(Synthesis of crude zinc halide phthalocyanine pigment)
In a molten salt of 200 ° C. of 356 parts of aluminum chloride and 6 parts of sodium chloride, 46 parts of zinc phthalocyanine was dissolved, cooled to 130 ° C., and stirred for 1 hour. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 10 parts per hour for 10 hours. Thereafter, chlorine was introduced at 0.8 parts per hour for 5 hours. The reaction solution was gradually poured into 3200 parts of water, then filtered and washed with water to obtain 107.8 parts of a crude zinc halide phthalocyanine pigment. The average number of bromine contained in one molecule of the crude zinc halide phthalocyanine pigment was 14.1 and the average number of chlorine was 1.9.
（粗製ハロゲン化コバルトフタロシアニン顔料の合成）
塩化アルミニウム３５６部および塩化ナトリウム６部の２００℃の溶融塩に、コバルトフタロシアニン４６部を溶解し、１３０℃まで冷却し２時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり１０部で１０時間滴下した。その後、塩素を１時間あたり０．８部で５時間導入した。この反応液を水４０００部に徐々に注入したのち、濾過、水洗して１２２．４部の粗製ハロゲン化コバルトフタロシアニン顔料を得た。粗製ハロゲン化コバルトフタロシアニン顔料の１分子内に含まれる平均臭素数は１３．８個、平均塩素数は２．２個であった。
(Synthesis of crude halogenated cobalt phthalocyanine pigment)
In a molten salt of 200 ° C. of 356 parts of aluminum chloride and 6 parts of sodium chloride, 46 parts of cobalt phthalocyanine was dissolved, cooled to 130 ° C., and stirred for 2 hours. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 10 parts per hour for 10 hours. Thereafter, chlorine was introduced at 0.8 parts per hour for 5 hours. The reaction solution was gradually poured into 4000 parts of water, then filtered and washed with water to obtain 122.4 parts of a crude cobalt halide phthalocyanine pigment. The average number of bromine contained in one molecule of the crude halogenated cobalt phthalocyanine pigment was 13.8 and the average number of chlorine was 2.2.
（粗製ハロゲン化ニッケルフタロシアニン顔料の合成）
塩化アルミニウム３５６部および塩化ナトリウム６部の２００℃の溶融塩に、ニッケルフタロシアニン４６部を溶解し、１３０℃まで冷却し２時間攪拌した。反応温度を１８０℃に昇温し、臭素を１時間あたり１０部で１０時間滴下した。その後、塩素を１時間あたり０．８部で５時間導入した。この反応液を水３２００部に徐々に注入したのち、濾過、水洗して１１９．８部の粗製ハロゲン化ニッケルフタロシアニン顔料を得た。粗製ハロゲン化ニッケルフタロシアニン顔料の１分子内に含まれる平均臭素数は１３．０個、平均塩素数は３．０個であった。
(Synthesis of crude halogenated nickel phthalocyanine pigment)
In a molten salt of 356 parts of aluminum chloride and 6 parts of sodium chloride at 200 ° C., 46 parts of nickel phthalocyanine was dissolved, cooled to 130 ° C. and stirred for 2 hours. The reaction temperature was raised to 180 ° C., and bromine was added dropwise at 10 parts per hour for 10 hours. Thereafter, chlorine was introduced at 0.8 parts per hour for 5 hours. The reaction solution was gradually poured into 3200 parts of water, then filtered and washed with water to obtain 119.8 parts of a crude nickel halide phthalocyanine pigment. The average number of bromines contained in one molecule of the crude halogenated nickel phthalocyanine pigment was 13.0, and the average number of chlorine was 3.0.
次に、下記の方法で粗製ハロゲン化金属フタロシアニン顔料を顔料化処理し、フタロシアニン系緑色顔料を製造した。
（フタロシアニン系緑色顔料１の作製）
粗製ハロゲン化銅フタロシアニン顔料１００部、塩化ナトリウム１００部、ジエチレングリコール５０部をステンレス製１ガロンニーダー（井上製作所製）に仕込み、７０℃で２時間混練した。次に、この混練物を５リットルの温水に投入し、７０℃に加熱しながら１時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、８０℃で一昼夜乾燥し、フタロシアニン系緑色顔料１を得た。
Next, the crude halogenated metal phthalocyanine pigment was pigmented by the following method to produce a phthalocyanine green pigment.
(Preparation of phthalocyanine green pigment 1)
100 parts of a crude copper halide phthalocyanine pigment, 100 parts of sodium chloride and 50 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 2 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, a phthalocyanine green pigment 1 was obtained.
（フタロシアニン系緑色顔料２の作製）
粗製ハロゲン化銅フタロシアニン顔料の代わりに、粗製ハロゲン化アルミニウムフタロシアニン顔料を用いた以外は、フタロシアニン系緑色顔料１と同様の方法でフタロシアニン系緑色顔料２を得た
（フタロシアニン系緑色顔料３の作製）
粗製ハロゲン化銅フタロシアニン顔料の代わりに、粗製ハロゲン化亜鉛フタロシアニン顔料を用いた以外は、フタロシアニン系緑色顔料１と同様の方法でフタロシアニン系緑色顔料３を得た。
(Preparation of phthalocyanine green pigment 2)
A phthalocyanine green pigment 2 was obtained in the same manner as the phthalocyanine green pigment 1 except that a crude aluminum halide phthalocyanine pigment was used instead of the crude halogenated copper phthalocyanine pigment (production of phthalocyanine green pigment 3).
A phthalocyanine green pigment 3 was obtained in the same manner as the phthalocyanine green pigment 1, except that a crude zinc halide phthalocyanine pigment was used instead of the crude copper halide phthalocyanine pigment.
（フタロシアニン系緑色顔料４の作製）
粗製ハロゲン化銅フタロシアニン顔料の代わりに、粗製ハロゲン化コバルトフタロシアニン顔料を用いた以外は、フタロシアニン系緑色顔料１と同様の方法でフタロシアニン系緑色顔料４を得た。
（フタロシアニン系緑色顔料５の作製）
粗製ハロゲン化銅フタロシアニン顔料の代わりに、粗製ハロゲン化ニッケルフタロシアニン顔料を用いた以外は、フタロシアニン系緑色顔料１と同様の方法でフタロシアニン系緑色顔料５を得た。
(Preparation of phthalocyanine green pigment 4)
A phthalocyanine green pigment 4 was obtained in the same manner as the phthalocyanine green pigment 1, except that a crude halogenated cobalt phthalocyanine pigment was used instead of the crude copper halide phthalocyanine pigment.
(Preparation of phthalocyanine green pigment 5)
A phthalocyanine green pigment 5 was obtained in the same manner as the phthalocyanine green pigment 1 except that a crude nickel halide phthalocyanine pigment was used instead of the crude copper halide phthalocyanine pigment.
（フタロシアニン系青色顔料１の作製）
粗製銅フタロシアニン顔料を５４０ｇ、硫酸６．０Ｌ中にて５℃以下で３時間撹拌して溶かし、ガラスフィルターで不溶物を除いた後、水６０Ｌに室温で注いだ。折出した結晶を濾過し、濾液の電気伝導度が２５μＳ-1になるまでよく水洗した。乾燥後取り出し、Ｘ線回折測定結果より、α型フタロシアニン顔料であることを確認した。
α型銅フタロシアニン顔料５２５部、塩化ナトリウム５００部、ジエチレングリコール２５０部、および色素誘導体（化合物Ａ−４８）２５部をステンレス製１ガロンニーダー（井上製作所製）に仕込み、７０℃で２時間混練した。次に、この混練物を５リットルの温水に投入し、７０℃に加熱しながら１時間攪拌してスラリー状とし、濾過、水洗を繰り返して塩化ナトリウム及びジエチレングリコールを除いた後、８０℃で一昼夜乾燥し、フタロシアニン系青色顔料１を得た。フタロシアニン系青色顔料１のＸ線回折測定結果より、ε型フタロシアニン顔料であることを確認した。
(Preparation of phthalocyanine blue pigment 1)
The crude copper phthalocyanine pigment was dissolved in 540 g of sulfuric acid (6.0 L) by stirring at 5 ° C. or less for 3 hours to remove insoluble matters with a glass filter, and then poured into 60 L of water at room temperature. The folded crystal was filtered and washed well with water until the electric conductivity of the filtrate reached 25 μS −1 . It took out after drying and it confirmed that it was an alpha phthalocyanine pigment from the X-ray-diffraction measurement result.
525 parts of α-type copper phthalocyanine pigment, 500 parts of sodium chloride, 250 parts of diethylene glycol, and 25 parts of a pigment derivative (Compound A-48) were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 70 ° C. for 2 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, a phthalocyanine blue pigment 1 was obtained. From the X-ray diffraction measurement result of the phthalocyanine blue pigment 1, it was confirmed that it was an ε-type phthalocyanine pigment.
（フタロシアニン系青色顔料２の作製）
粗製銅フタロシアニン顔料の代わりに、粗製アルミニウムフタロシアニン顔料を用いた以外は、フタロシアニン系青色顔料１と同様の方法でフタロシアニン系青色顔料２を得た。フタロシアニン系青色顔料２のＸ線回折測定結果より、ε型フタロシアニン顔料であることを確認した。
（フタロシアニン系青色顔料３の作製）
粗製銅フタロシアニン顔料の代わりに、粗製亜鉛フタロシアニン顔料を用いた以外は、フタロシアニン系青色顔料１と同様の方法でフタロシアニン系青色顔料３を得た。フタロシアニン系青色顔料３のＸ線回折測定結果より、ε型フタロシアニン顔料であることを確認した。
(Preparation of phthalocyanine blue pigment 2)
A phthalocyanine blue pigment 2 was obtained in the same manner as the phthalocyanine blue pigment 1 except that a crude aluminum phthalocyanine pigment was used instead of the crude copper phthalocyanine pigment. From the X-ray diffraction measurement result of the phthalocyanine blue pigment 2, it was confirmed to be an ε-type phthalocyanine pigment.
(Preparation of phthalocyanine blue pigment 3)
A phthalocyanine blue pigment 3 was obtained in the same manner as the phthalocyanine blue pigment 1 except that a crude zinc phthalocyanine pigment was used instead of the crude copper phthalocyanine pigment. From the X-ray diffraction measurement result of the phthalocyanine blue pigment 3, it was confirmed to be an ε-type phthalocyanine pigment.
（フタロシアニン系青色顔料４の作製）
粗製銅フタロシアニン顔料の代わりに、粗製コバルトフタロシアニン顔料を用いた以外は、フタロシアニン系青色顔料１と同様の方法でフタロシアニン系青色顔料４を得た。フタロシアニン系青色顔料４のＸ線回折測定結果より、ε型フタロシアニン顔料であることを確認した。
（フタロシアニン系青色顔料５の作製）
粗製銅フタロシアニン顔料の代わりに、粗製ニッケルフタロシアニン顔料を用いた以外は、フタロシアニン系青色顔料１と同様の方法でフタロシアニン系青色顔料５を得た。フタロシアニン系青色顔料５のＸ線回折測定結果より、ε型フタロシアニン顔料であることを確認した。
(Preparation of phthalocyanine blue pigment 4)
A phthalocyanine blue pigment 4 was obtained in the same manner as the phthalocyanine blue pigment 1 except that a crude cobalt phthalocyanine pigment was used instead of the crude copper phthalocyanine pigment. From the X-ray diffraction measurement result of the phthalocyanine blue pigment 4, it was confirmed to be an ε-type phthalocyanine pigment.
(Preparation of phthalocyanine blue pigment 5)
A phthalocyanine blue pigment 5 was obtained in the same manner as the phthalocyanine blue pigment 1 except that a crude nickel phthalocyanine pigment was used instead of the crude copper phthalocyanine pigment. From the X-ray diffraction measurement result of the phthalocyanine blue pigment 5, it was confirmed to be an ε-type phthalocyanine pigment.
[実施例１〜２０、比較例１〜３４]
表１４に示す組成のフタロシアニン系顔料を含む下記の組成の混合物を均一に撹拌混合し、直径０．１ｍｍのジルコニアビーズを用いて、ｐｉｃｏミルで１０時間分散した後、５μｍのフィルタで濾過し、顔料分散体を作製した。
フタロシアニン系顔料の合計 １３．５部
色素誘導体（化合物Ａ−４８） １．５部
アクリル樹脂溶液 ４０．０部
ジペンタエリストリトールペンタアクリレートおよびヘキサアクリレート
（東亞合成社製「アロニックスＭ４００」） ７．０部
シクロヘキサノン ３８．０部
[Examples 1-20, Comparative Examples 1-34]
A mixture of the following composition containing the phthalocyanine pigment of the composition shown in Table 14 was uniformly stirred and mixed, dispersed with a pico mill for 10 hours using zirconia beads having a diameter of 0.1 mm, and then filtered with a 5 μm filter. A pigment dispersion was prepared.
Total of phthalocyanine pigments 13.5 parts Dye derivative (Compound A-48) 1.5 parts Acrylic resin solution 40.0 parts Dipentaerythritol pentaacrylate and hexaacrylate (“Aronix M400” manufactured by Toagosei Co., Ltd.) 0 parts cyclohexanone 38.0 parts
ついで、下記組成の混合物を均一になるように攪拌混合した後、１μｍのフィルタで濾過し、着色組成物を作製した。
上記顔料分散体 ５３．３３部
アクリル樹脂溶液 ７．７５部
光重合開始剤 ２．２４部
（チバスペシャルティケミカルズ社製「イルガキュア９０７」）
界面活性剤（ビックケミー社製「ＢＹＫ−３２３」） ０．０３部
貯蔵安定剤（北興化学社製「ＴＰＰ」） ０．２０部
シクロへキサノン ３６．４５部
Next, a mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a colored composition.
Pigment dispersion 53.33 parts Acrylic resin solution 7.75 parts Photopolymerization initiator 2.24 parts ("Irgacure 907" manufactured by Ciba Specialty Chemicals)
Surfactant ("BYK-323" manufactured by Big Chemie) 0.03 parts Storage stabilizer ("TPP" manufactured by Hokuko Chemical Co., Ltd.) 0.20 parts Cyclohexanone 36.45 parts
（１）色調の鮮明度評価
ガラス基板に、スピンコートにより、Ｃ光源で緑色塗膜はｙ＝０．５０、青色塗膜はｙ＝０．１７の色度になるような膜厚で、実施例１〜２０、比較例１〜３２で得られた着色組成物を塗布した。乾燥後、露光機にて全面露光し光硬化させた後、２３０℃のオーブンで１時間加熱し熱硬化させ、サンプル基板を得た。サンプル基板を２枚の偏光板の間に挟み、偏光板が平行の時の輝度と偏光板が直行の時の輝度を下記の方法で測定し、色調の鮮明度として、偏光板が平行のときの輝度と、直行のときの輝度との比を算出した。
（色調の鮮明度）＝（平行のときの輝度）／（直行のときの輝度）
(1) Evaluation of color tone vividness A glass substrate was spin-coated with a C light source at a film thickness such that y = 0.50 for a green paint film and y = 0.17 for a blue paint film. The coloring compositions obtained in Examples 1 to 20 and Comparative Examples 1 to 32 were applied. After drying, the entire surface was exposed and photocured with an exposure machine, and then heated and cured in an oven at 230 ° C. for 1 hour to obtain a sample substrate. The sample substrate is sandwiched between two polarizing plates, the luminance when the polarizing plate is parallel and the luminance when the polarizing plate is perpendicular are measured by the following methods, and the brightness when the polarizing plate is parallel is measured as the sharpness of the color tone. And the ratio of the brightness at the time of direct was calculated.
(Color tone sharpness) = (Luminance when parallel) / (Luminance when going straight)
サンプル基板を２枚の偏光板の間に挟んだ状態における輝度の測定法について説明する。
サンプル基板を挟んだ２枚の偏光板の、一方の偏光板側から光を照射すると、照射した光は、一方の偏光板を通過して偏光され、ガラス基板上に塗布された着色組成物の乾燥塗膜を通過し、他方の偏光板に到達する。２枚の偏光板の偏光面が平行であれば、光は偏光板を透過するが、偏光面が直行している場合には、光は偏光板により遮断される。この透過光を、偏光板が平行のときの輝度および偏光板が直行の時の輝度として測定した。
なお、輝度計としては色彩輝度計（トプコン社製「ＢＭ−５Ａ」）、偏光板としては偏光板（日東電工社製「ＮＰＦ−Ｇ１２２０ＤＵＮ」）を用いた。測定に際しては、不要光を遮断するために、測定部分に１ｃｍ角の孔を開けた黒色のマスクを当てた。
A method for measuring luminance in a state where the sample substrate is sandwiched between two polarizing plates will be described.
When light is irradiated from one polarizing plate side of two polarizing plates sandwiching the sample substrate, the irradiated light is polarized through one polarizing plate and applied to the glass composition on the glass substrate. Passes through the dried coating and reaches the other polarizing plate. If the polarization planes of the two polarizing plates are parallel, light passes through the polarizing plate, but if the polarization planes are perpendicular, the light is blocked by the polarizing plate. The transmitted light was measured as the luminance when the polarizing plate was parallel and the luminance when the polarizing plate was orthogonal.
A color luminance meter ("BM-5A" manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko Corporation) was used as the polarizing plate. In the measurement, a black mask with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.
偏光板によって偏光された光が着色組成物の乾燥塗膜を通過するときには、顔料粒子による散乱等が起こり、偏光面の一部にずれを生じると、偏光板が平行のときは偏光板を透過する光量が減り、偏向板が直行のときは偏光板を一部光が透過する。すなわち、着色組成物の乾燥塗膜中の顔料粒子により散乱が起こると、平行のときの輝度が低下し、かつ直行のときの輝度が増加するため、色調の鮮明度の値が低くなる。従って、色調の鮮明度の値が大きい程、鮮明度が優れており、より優れている。なお、色調の鮮明度の誤差範囲は±９０であり、その範囲を超えた結果は明らかな差である。 When the light polarized by the polarizing plate passes through the dried coating film of the colored composition, scattering by pigment particles occurs, and if a part of the polarizing plane is displaced, the polarizing plate is transmitted when the polarizing plate is parallel. When the amount of light to be reduced is reduced and the deflection plate is perpendicular, a part of the light is transmitted through the polarizing plate. That is, when scattering occurs due to the pigment particles in the dried coating film of the coloring composition, the brightness when parallel is lowered and the brightness when perpendicular is increased, the value of the sharpness of the color tone is lowered. Therefore, the larger the color tone sharpness value, the better the sharpness and the better. Note that the error range of the definition of color tone is ± 90, and the result exceeding this range is a clear difference.
（２）色表示領域評価
得られた着色組成物を、１００ｍｍ×１００ｍｍのガラス基板上に、スピンコーターを用いて５００ｒｐｍ、１０００ｒｐｍ、１５００ｒｐｍ、２０００ｒｐｍの回転数で塗布し、膜厚が異なる４種の塗布基板を得た。乾燥後、露光機にて全面露光し光硬化させた後、２３０℃のオーブンで１時間加熱し熱硬化させた塗膜を得た。得られた橙色塗膜のＣ光源での色度（Ｙ，ｘ，ｙ）を顕微分光光度計（オリンパス光学社製「ＯＳＰ−ＳＰ１００」）を用いて測定した。４組の色度・分光測定結果から、緑色塗膜はｙ＝０．５０、青色塗膜はｙ＝０．１７の時の、ｘおよびＹを求めた。
濃度方向であるｙを固定した場合、Ｙが大きいほど光透過量が多く、色表示領域が広く優れている。
さらに、ｘの値が小さくなるほど、短波長の透過領域が広がっていることを示しているため、色表示領域が広く優れているといえる。より好ましくは、Ｙが大きい、かつｘが小さい場合である。
ｘの誤差範囲は±０．００２であり、その範囲を超えた結果は明らかな差である。
Ｙの誤差範囲は±０．１であり、その範囲を超えた結果は明らかな差である。
(2) Color display region evaluation The obtained colored composition was applied on a glass substrate of 100 mm × 100 mm at a rotation speed of 500 rpm, 1000 rpm, 1500 rpm, 2000 rpm using a spin coater, and four types having different film thicknesses. A coated substrate was obtained. After drying, the whole surface was exposed and photocured with an exposure machine, and then heated in a 230 ° C. oven for 1 hour to obtain a heat-cured coating film. The chromaticity (Y, x, y) of the obtained orange coating film with a C light source was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). From the four sets of chromaticity / spectral measurement results, x and Y were obtained when the green coating film was y = 0.50 and the blue coating film was y = 0.17.
When y, which is the density direction, is fixed, the larger Y is, the more light is transmitted, and the color display area is wide and excellent.
Furthermore, it can be said that the smaller the value of x is, the wider and better the color display region is because the transmission region of the short wavelength is widened. More preferably, Y is large and x is small.
The error range of x is ± 0.002, and the result beyond that range is a clear difference.
The error range of Y is ± 0.1, and the result beyond this range is a clear difference.
（３）着色力評価
上記（２）色表示領域評価で得られた塗膜のＣ光源での色度（Ｙ，ｘ，ｙ）を顕微分光光度計（オリンパス光学社製「ＯＳＰ−ＳＰ１００」）を用いて測定した分光測定結果、および膜厚測定結果から、可視光領域の最大吸収が２（透過率１％）になる時の塗膜の厚みを算出し、着色力値とした。着色力値が小さい程、体積あたりの着色力が大きいことを示しており、優れているといえる。
着色力の誤差範囲は±０．０９であり、その範囲を超えた結果は明らかな差である。
(3) Evaluation of tinting strength The chromaticity (Y, x, y) of the coating film obtained in the above (2) color display area evaluation with a C light source is determined by a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.) From the spectroscopic measurement result measured using the film thickness and the film thickness measurement result, the thickness of the coating film when the maximum absorption in the visible light region was 2 (transmittance 1%) was calculated and used as the coloring power value. It can be said that the smaller the coloring power value is, the higher the coloring power per volume is.
The error range of the coloring power is ± 0.09, and the result exceeding the range is a clear difference.
（４）保存安定性評価
得られた着色組成物の４０℃で７日静置前後の粘度を、Ｅ型粘度計（東機産業社製「Ｒ１１０」）を用いて２５℃で測定した。４０℃で７日静置前後の粘度の変化量が１割未満を◎、１割以上２割未満を○、２割以上５割未満を△、５割以上を×として、保存安定性を評価した。
粘度の変化量が小さい程、保存安定していることを示しており、優れているといえる。
(4) Storage Stability Evaluation The viscosity of the obtained colored composition before and after standing for 7 days at 40 ° C. was measured at 25 ° C. using an E-type viscometer (“R110” manufactured by Toki Sangyo Co., Ltd.). The amount of change in viscosity before and after standing at 40 ° C for 7 days is less than 10% ◎ 10% to less than 20% ○, 20% to less than 50% △, 50% or more is evaluated as storage stability did.
It can be said that the smaller the change in viscosity is, the better the storage stability is.
（１）色調の鮮明度評価、（２）色表示領域評価、（３）着色力評価、（４）保存安定性評価の結果を表１４に表す。
実施例１は、色調の鮮明度が比較例１（現行品）と同等であり、保存安定性が若干悪い以外の項目、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、優れている。
実施例２と３は、保存安定性が若干悪い以外の項目、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、優れている。
実施例１〜３より、本発明の着色組成物は、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいて現行品より優れていることがわかる。中でも、より好ましい範囲でアルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料を含む実施例２は、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいてバランスが取れ、非常に優れている。
In Example 1, the color tone sharpness is equivalent to that of Comparative Example 1 (current product), items other than storage stability being slightly worse, color display region x, color display region Y, and coloring power are improved. Are better.
Examples 2 and 3 are excellent in items other than storage stability being slightly poor, color tone sharpness, color display region x, color display region Y, and coloring power are improved.
From Examples 1 to 3, it can be seen that the colored composition of the present invention is superior to the current product in all of the vividness of the color tone, the width of the color display area, and the coloring power. Among them, Example 2 containing an aluminum phthalocyanine pigment and a zinc phthalocyanine pigment in a more preferable range is balanced and excellent in all of the vividness of the color tone, the width of the color display area, and the coloring power.
実施例４は、色調の鮮明度、色表示領域ｘ、色表示領域Ｙが現行品と同等で、着色力が改善されており、やや優れている。
実施例５〜１０は、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、非常に優れている。
実施例４〜１０より、本発明の着色組成物は、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいて現行品より優れていることがわかる。中でも、より好ましい範囲でアルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料と銅フタロシアニン顔料を含む実施例７〜１０は、非常に優れており、さらに実施例１０はすべての項目でバランスよく良好で最も優れている。
In Example 4, the color tone sharpness, the color display area x, and the color display area Y are the same as the current product, the coloring power is improved, and it is slightly superior.
In Examples 5 to 10, the color tone definition, the color display region x, the color display region Y, and the coloring power are improved, which is very excellent.
From Examples 4 to 10, it can be seen that the colored composition of the present invention is superior to the current product in all of the vividness of the color tone, the width of the color display area, and the coloring power. Among them, Examples 7 to 10 containing an aluminum phthalocyanine pigment, a zinc phthalocyanine pigment, and a copper phthalocyanine pigment in a more preferable range are very excellent, and Example 10 is excellent and well balanced in all items.
比較例２〜１７と比較例１（現行品）の比較で、２種以上の金属フタロシアニン顔料を用いても、アルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料のいずれか一方しか用いない場合には、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力のすべてを改善することは困難であり、本発明の組成物でのみ、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力のすべてが改善されることが明らかとなっている。 In comparison between Comparative Examples 2 to 17 and Comparative Example 1 (current product), when only one of aluminum phthalocyanine pigment and zinc phthalocyanine pigment is used even when two or more kinds of metal phthalocyanine pigments are used, the color tone is clear. It is difficult to improve the degree of color, the color display area x, the color display area Y, and the coloring power. Only with the composition of the present invention, the color tone sharpness, the color display area x, the color display area Y, and the coloring power. It has become clear that all of these will be improved.
実施例１１は、色調の鮮明度が比較例１８（現行品）と同等であり、保存安定性が若干悪い以外の項目、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、優れている。
実施例１２と１３は、保存安定性が若干悪い以外の項目、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、優れている。
実施例１１〜１３より、本発明の着色組成物は、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいて現行品より優れていることがわかる。中でも、より好ましい範囲でアルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料を含む実施例１２は、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいてバランスが取れ、非常に優れている。
In Example 11, the color tone sharpness is equivalent to that of Comparative Example 18 (current product), items other than storage stability being slightly worse, the color display region x, the color display region Y, and the coloring power are improved. Are better.
Examples 12 and 13 are excellent in items other than storage stability being slightly worse, color tone sharpness, color display region x, color display region Y, and coloring power are improved.
From Examples 11 to 13, it can be seen that the colored composition of the present invention is superior to the current product in all of the vividness of the color tone, the width of the color display region, and the coloring power. Among them, Example 12, which contains aluminum phthalocyanine pigment and zinc phthalocyanine pigment in a more preferable range, is balanced and excellent in all of the vividness of the color tone, the width of the color display area, and the coloring power.
実施例１４は、色調の鮮明度、色表示領域ｘ、色表示領域Ｙが現行品と同等で、着色力が改善されており、やや優れている。
実施例１５〜２０は、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力が改善されており、非常に優れている。
実施例１４〜２０より、本発明の着色組成物、色調の鮮明性、色表示領域の広さおよび着色力のすべてにおいて現行品より優れていることがわかる。中でも、より好ましい範囲でアルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料と銅フタロシアニン顔料を含む実施例１７〜２０、は非常に優れており、さらに実施例２０はすべての項目でバランスよく良好で最も優れている。
In Example 14, the clearness of the color tone, the color display area x, and the color display area Y are the same as the current product, the coloring power is improved, and it is slightly superior.
In Examples 15 to 20, the color tone definition, the color display region x, the color display region Y, and the coloring power are improved, which is very excellent.
From Examples 14 to 20, it can be seen that the colored composition of the present invention, the clearness of the color tone, the width of the color display area and the coloring power are all superior to the current product. Among them, Examples 17 to 20 including an aluminum phthalocyanine pigment, a zinc phthalocyanine pigment, and a copper phthalocyanine pigment in a more preferable range are very excellent, and Example 20 is excellent and well balanced in all items.
比較例１９〜３４と比較例１８（現行品）の比較で、２種以上の金属フタロシアニン顔料を用いても、アルミニウムフタロシアニン顔料と亜鉛フタロシアニン顔料のいずれか一方しか用いない場合には、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力を改善することは困難であり、本発明の組成物でのみ、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力のすべてが改善されることが明らかとなっている。
実施例の結果からも明らかなように、本発明の着色組成物は、金属フタロシアニン顔料がハロゲン化されているか否かにかかわらず有効であり、従来の技術では達成できなかった、色調の鮮明度、色表示領域ｘ、色表示領域Ｙ、着色力のすべてにおけるバランスの取れた改善がされており、非常に優れた着色組成物である。
In comparison between Comparative Examples 19 to 34 and Comparative Example 18 (current product), when only one of aluminum phthalocyanine pigment and zinc phthalocyanine pigment is used even when two or more kinds of metal phthalocyanine pigments are used, the color tone is clear. It is difficult to improve the degree of color, the color display area x, the color display area Y, and the coloring power. Only with the composition of the present invention, all of the color tone clarity, the color display area x, the color display area Y, and the coloring power. Has been shown to improve.
As is clear from the results of the examples, the coloring composition of the present invention is effective regardless of whether or not the metal phthalocyanine pigment is halogenated, and the sharpness of the color tone that cannot be achieved by the prior art. The color display area x, the color display area Y, and the coloring power are all well-balanced and are excellent coloring compositions.
本発明の着色組成物は、鮮明な色調、広い色表示領域、高い着色力を発揮する良好なインキ及び塗料として用いることができ、グラビアインキ、自動車用、木材用、金属用等の各種一般塗料、磁気テープのバックコート塗料、ラジエーションキュアー型インキ、インクジェットプリンター用インキ、カラーフィルター用インキ等の用途に適当できる。 The coloring composition of the present invention can be used as a clear ink, a wide color display area, a good ink and paint exhibiting high coloring power, and various general paints such as gravure inks, automobiles, woods, and metals. It is suitable for applications such as magnetic tape back coat paint, radiation cure ink, ink jet printer ink and color filter ink.
Claims (4)
The content of aluminum phthalocyanine pigment based on the total weight of the metal phthalocyanine pigment is 5 to 45% by weight, the content of zinc phthalocyanine pigment is 30 to 80% by weight, and the content of copper phthalocyanine pigment is 10 to 60%. The coloring composition according to claim 2, wherein the coloring composition is% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006026663A JP4983029B2 (en) | 2006-02-03 | 2006-02-03 | Coloring composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006026663A JP4983029B2 (en) | 2006-02-03 | 2006-02-03 | Coloring composition |
Publications (2)
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| TWI506306B (en) * | 2007-11-22 | 2015-11-01 | Toyo Ink Mfg Co | Green colored composition for color filter, and color filter |
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| JP4640406B2 (en) * | 2007-11-27 | 2011-03-02 | セイコーエプソン株式会社 | Color filter ink, color filter ink set, color filter, image display device, and electronic device |
| JP2009127027A (en) * | 2007-11-28 | 2009-06-11 | Seiko Epson Corp | Ink for color filter, ink set for color filter, color filter, image display device, and electronic equipment |
| JP2009169214A (en) | 2008-01-18 | 2009-07-30 | Seiko Epson Corp | Color filter ink set, color filter, image display device and electronic device |
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| JP2823885B2 (en) * | 1989-04-21 | 1998-11-11 | 新電元工業株式会社 | Function-separated organic electrophotographic photoreceptor |
| JPH0645586A (en) * | 1992-07-23 | 1994-02-18 | Res Dev Corp Of Japan | Phthalocyanine thin film, manufacture thereof and multilayer film using that |
| JP3077458B2 (en) * | 1993-07-23 | 2000-08-14 | 東洋インキ製造株式会社 | Method for producing aluminum phthalocyanine composition |
| JP2001089682A (en) * | 1999-07-15 | 2001-04-03 | Dainichiseika Color & Chem Mfg Co Ltd | Composite pigment, coloring composition and image recording agent |
| JP2001064519A (en) * | 1999-08-25 | 2001-03-13 | Hitachi Chem Co Ltd | Green resin composition, photosensitive green resin composition, green image forming photosensitive liquid, preparation of colored image and colored filter |
| JP4346230B2 (en) * | 2000-09-12 | 2009-10-21 | 三菱化学株式会社 | Color filter composition and color filter |
| JP3945242B2 (en) * | 2000-12-22 | 2007-07-18 | 東洋インキ製造株式会社 | Coloring composition for color filter and color filter |
| JP4407097B2 (en) * | 2001-02-23 | 2010-02-03 | Ｄｉｃ株式会社 | Color filter |
| JP2003176424A (en) * | 2001-12-12 | 2003-06-24 | Dainippon Ink & Chem Inc | Green coloring matter composition and color filter |
| JP2004123841A (en) * | 2002-09-30 | 2004-04-22 | Fuji Xerox Co Ltd | Photoconductive organic pigment, photoconductive organic pigment dispersion, electrophotographic photoconductor and electrophotogrtaphic apparatus using the same |
| JP5181410B2 (en) * | 2004-03-04 | 2013-04-10 | 三菱化学株式会社 | Phthalocyanine composition, photoconductive material using the same, electrophotographic photosensitive member, electrophotographic photosensitive member cartridge, and image forming apparatus |
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