JP5173333B2 - Pigment composition, coloring composition using the same, and color filter - Google Patents
Pigment composition, coloring composition using the same, and color filter Download PDFInfo
- Publication number
- JP5173333B2 JP5173333B2 JP2007233829A JP2007233829A JP5173333B2 JP 5173333 B2 JP5173333 B2 JP 5173333B2 JP 2007233829 A JP2007233829 A JP 2007233829A JP 2007233829 A JP2007233829 A JP 2007233829A JP 5173333 B2 JP5173333 B2 JP 5173333B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- reference example
- pigment composition
- acid group
- color filter
- 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
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 115
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 238000004040 coloring Methods 0.000 title claims abstract description 13
- 239000012860 organic pigment Substances 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000011248 coating agent Substances 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000011164 primary particle Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 abstract description 19
- 239000002253 acid Substances 0.000 description 50
- 239000000976 ink Substances 0.000 description 30
- 230000000052 comparative effect Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- 239000002245 particle Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 9
- 239000003086 colorant Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- -1 sizing color Substances 0.000 description 6
- 125000000542 sulfonic acid group Chemical group 0.000 description 6
- PPPFYBPQAPISCT-UHFFFAOYSA-N 2-hydroxypropyl acetate Chemical compound CC(O)COC(C)=O PPPFYBPQAPISCT-UHFFFAOYSA-N 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 2
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000003021 water soluble solvent Substances 0.000 description 2
- MJQHDSIEDGPFAM-UHFFFAOYSA-N (3-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(=O)C1=CC=CC=C1 MJQHDSIEDGPFAM-UHFFFAOYSA-N 0.000 description 1
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- INCJNDAQNPWMPZ-UHFFFAOYSA-N 3-amino-4-methoxybenzamide Chemical compound COC1=CC=C(C(N)=O)C=C1N INCJNDAQNPWMPZ-UHFFFAOYSA-N 0.000 description 1
- FBLAHUMENIHUGG-UHFFFAOYSA-N 3-hydroxy-n-(2-methylphenyl)naphthalene-2-carboxamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC2=CC=CC=C2C=C1O FBLAHUMENIHUGG-UHFFFAOYSA-N 0.000 description 1
- WGYFINWERLNPHR-UHFFFAOYSA-N 3-nitroanisole Chemical compound COC1=CC=CC([N+]([O-])=O)=C1 WGYFINWERLNPHR-UHFFFAOYSA-N 0.000 description 1
- VPXCXBHLKDPWQV-UHFFFAOYSA-N 5-amino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(Cl)C(S(O)(=O)=O)=C1 VPXCXBHLKDPWQV-UHFFFAOYSA-N 0.000 description 1
- DSBIJCMXAIKKKI-UHFFFAOYSA-N 5-nitro-o-toluidine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N DSBIJCMXAIKKKI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- IPHJYJHJDIGARM-UHFFFAOYSA-M copper phthalocyaninesulfonic acid, dioctadecyldimethylammonium salt Chemical compound [Cu+2].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC.C=1C(S(=O)(=O)[O-])=CC=C(C(=NC2=NC(C3=CC=CC=C32)=N2)[N-]3)C=1C3=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 IPHJYJHJDIGARM-UHFFFAOYSA-M 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- OHAXNCGNVGGWSO-UHFFFAOYSA-N n-(4-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=C(Cl)C=C1 OHAXNCGNVGGWSO-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 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 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Abstract
Description
本発明は、顔料組成物、着色組成物およびカラーフィルターに関する。 The present invention relates to a pigment composition, a coloring composition, and a color filter.
高分子有機化合物の着色剤として顔料を用いる例は多数知られていて、例えば、グラビア印刷インキなどの各種印刷インキ、サイジングカラー、バインダーカラー、コーティング剤、各種塗料、電子写真用乾式トナーまたは湿式トナー、熱転写記録用インキ、筆記具用インキなどが挙げられる（例えば、特許文献１および２）。 Many examples of using a pigment as a colorant for a polymer organic compound are known. For example, various printing inks such as gravure printing ink, sizing color, binder color, coating agent, various paints, dry toner or wet toner for electrophotography , Thermal transfer recording ink, writing instrument ink, and the like (for example, Patent Documents 1 and 2).
しかし、カラーフィルターの画素形成用塗布液やインクジェットインクに求められる高い透明性や色の鮮明性などの特性を十分に満足させる顔料着色剤は知られていない。これらの用途に用いられる顔料の１次粒子径を数十乃至数百ｎｍレベルに微細化させ、透明性や鮮明性を向上させようとすると、微細化により顔料粒子自体の再凝集力が強まり、顔料の分散性および分散安定性が悪くなる。そこで、分散剤などを使用した例（例えば、特許文献３〜５）も知られているが、上記用途で求められる特性を得るには未だ不十分である。そのため上記従来技術で調製された顔料着色剤では、現状において分散性、分散安定性、透明性および鮮明性などの全てを十分には満足させることができていない。 However, there is no known pigment colorant that sufficiently satisfies characteristics such as high transparency and color sharpness required for a color filter pixel forming coating liquid and inkjet ink. If the primary particle diameter of the pigment used in these applications is refined to a level of several tens to several hundreds of nanometers to improve transparency and sharpness, the reaggregation force of the pigment particles themselves is increased by the refinement, The dispersibility and dispersion stability of the pigment are deteriorated. Then, although the example (for example, patent documents 3-5) using a dispersing agent etc. is also known, it is still inadequate to obtain the characteristic calculated | required by the said use. For this reason, the pigment colorants prepared by the above-described prior art cannot satisfy all of the dispersibility, dispersion stability, transparency, and sharpness at present.
従って本発明の目的は、分散性、分散安定性、透明性および鮮明性などに十分に優れた顔料組成物、該顔料組成物を含む着色組成物およびカラーフィルターを提供することである。 Accordingly, an object of the present invention is to provide a pigment composition sufficiently excellent in dispersibility, dispersion stability, transparency, sharpness, and the like, a coloring composition containing the pigment composition, and a color filter.
上記目的は以下の本発明によって達成される。すなわち、本発明は、有機顔料と、下記一般式（３）で表される化合物とを含むことを特徴とする顔料組成物を提供する。 The above object is achieved by the present invention described below. That is, the present invention provides an organic pigment, a pigment composition which comprises a compound represented by the following general formula (3).
（前記一般式（３）式中、Ｘは、水素原子、または１個もしくは複数個の任意の置換基を表し、Ｑは、水素原子、または１個もしくは複数個の任意の置換基を有してもよいフェニル基を表し、Ｒは、１個または複数個の任意の置換基を有してもよい芳香環を表す。但し、前記一般式（３）で表される化合物は、少なくとも１個のＣＯＯＭまたはＳＯ3Ｍ（Ｍは、水素原子、金属原子、アンモニウム基、有機アミン基または４級アンモニウム基を表す。）で表される置換基を有する。） (In the general formula (3), X is, represents the water atom or one or a plurality of optional substituents,, Q is have a hydrogen atom or one or a plurality of arbitrary substituents, It represents a phenyl group which may be, R represents an aromatic ring which may have one or more optional substituents. However, the compound represented by the general formula (3) is no less Both have a substituent represented by one COOM or SO 3 M (M represents a hydrogen atom, a metal atom, an ammonium group, an organic amine group, or a quaternary ammonium group.)
上記本発明の顔料組成物においては、前記有機顔料が、Ｃ．Ｉ．ピグメントレッド１２２、Ｃ．Ｉ．ピグメントレッド１７７、Ｃ．Ｉ．ピグメントレッド２５４およびＣ．Ｉ．ピグメントバイオレット１９から選ばれる少なくとも１種であること；前記有機顔料の１次粒子径が、１００ｎｍ以下であること；前記有機顔料１００質量部に対して、前記一般式（３）で表される化合物（以下「本発明の酸基導入色素」という場合がある）を０．１〜３０質量部の配合割合で含むことが好ましい。 In the pigment composition of the present invention, the organic pigment is, C. I. Pigment red 122, C.I. I. Pigment red 177, C.I. I. Pigment red 254 and C.I. I. Compounds of to the organic pigment 100 parts by weight, represented by the general formula (3); is at least one selected from Pigment Violet 19; primary particle diameter of the organic pigment, it is 100nm or less It is preferable to contain a product ( hereinafter sometimes referred to as “the acid group-introducing dye of the present invention”) at a blending ratio of 0.1 to 30 parts by mass.
また、本発明は、前記顔料組成物と、被膜形成材料とを含むことを特徴とする着色組成物を提供する。該着色組成物は、カラーフィルター画素形成用塗布液またはインクジェットインクとして特に有用である。また、本発明は、上記着色組成物を用いて形成された画素を備えることを特徴とするカラーフィルターを提供する。 Further, the present invention provides a front Kikao sweetener composition, a coloring composition comprising a film-forming material. Colored composition, color filter pixels forming coating Ekima others are particularly useful as a jet in click. The present invention also provides a color filter characterized by Rukoto includes a pixel formed by using the coloring composition.
本発明によれば、分散性、分散安定性、透明性および鮮明性などに十分に優れた顔料組成物、該顔料組成物を含む着色組成物およびカラーフィルターを提供することができる。 According to the present invention, it is possible to provide a pigment composition that is sufficiently excellent in dispersibility, dispersion stability, transparency, sharpness, and the like, a coloring composition containing the pigment composition, and a color filter.
次に好ましい実施の形態を挙げて本発明をさらに詳細に説明する。
本発明で使用する前記本発明の酸基導入色素は、ジアゾ成分として下記一般式（４）、（５）または（６）で表される化合物のジアゾニウム塩を、下記一般式（７）で表される化合物をカップラー成分として用いて、公知のカップリング方法で得ることができるが、その製造方法は特に限定されない。但し、上記のカップリング反応に際しては、得られる一般式（１）、（２）および（３）で表される化合物が、それぞれ、少なくとも１個のＣＯＯＭ基またはＳＯ3Ｍ基を有するように、一般式（４）、（５）、（６）、（７）で表される化合物を選択して使用することが必要である。
Next, the present invention will be described in more detail with reference to preferred embodiments.
The acid group-introduced dye of the present invention used in the present invention represents a diazonium salt of a compound represented by the following general formula (4), (5) or (6) as a diazo component, represented by the following general formula (7). The compound to be produced can be obtained by a known coupling method using the compound as a coupler component, but the production method is not particularly limited. However, in the above coupling reaction, the resulting compounds represented by the general formulas (1), (2), and (3) each have at least one COOM group or SO 3 M group. It is necessary to select and use the compounds represented by the general formulas (4), (5), (6) and (7).
上記一般式（４）〜（６）で表される化合物としては、例えば、２−アミノ−４−メチル−５−クロロベンゼンスルホン酸、３−アミノ−６−クロロベンゼンスルホン酸、３−アミノ−４−メトキシベンズアミド、２−アミノ−４−ニトロトルエン、２−アミノナフタレンスルホン酸、１−アミノ−４−ブロモアントラキノン−２−スルホン酸、α−アミノアントラキノン、アニリン、４−アミノ−３−ニトロトルエン、４−アミノ−３−メトキシニトロベンゼンなどが挙げられるが、これらに限定されない。
Examples of the compounds represented by the general formulas (4) to (6) include 2-amino-4-methyl-5-chlorobenzenesulfonic acid, 3-amino-6-chlorobenzenesulfonic acid, and 3-amino-4- Methoxybenzamide, 2-amino-4-nitrotoluene, 2-aminonaphthalenesulfonic acid, 1-amino-4-bromoanthraquinone-2-sulfonic acid, α-aminoanthraquinone, aniline, 4-amino-3-nitrotoluene, 4-amino Examples include, but are not limited to, 3-methoxynitrobenzene.
上記一般式（７）で表される化合物としては、例えば、２−ヒドロキシ−３−フェニルカルバモイルナフタレン、２−ヒドロキシ−３−（２−メチルフェニルカルバモイル）ナフタレン、２−ヒドロキシ−３−（４−クロロフェニルカルバモイル）ナフタレン、２−ヒドロキシ−３−ナフトエ酸アニライド−４’−スルホン酸などが挙げられるが、これらに限定されない。
Examples of the compound represented by the general formula (7) include 2-hydroxy-3-phenylcarbamoylnaphthalene, 2-hydroxy-3- (2-methylphenylcarbamoyl) naphthalene, 2-hydroxy-3- (4- Chlorophenylcarbamoyl) naphthalene, 2-hydroxy-3-naphthoic acid anilide-4′-sulfonic acid and the like, but are not limited thereto.
前記一般式（１）〜（７）において、カルボン酸基およびスルホン酸基以外の任意の置換基としては、例えば、ニトロ基、ヒドロキシ基、アルコキシ基、アルキル基、ハロゲン基などの置換基が挙げられるが、これらに限られない。また、カルボン酸基およびスルホン酸基と塩を形成する金属としては、例えば、Ｌｉ、Ｎａ、Ｋなどのアルカリ金属、Ｃａ、Ｂａ、Ａｌ、Ｍｎ、Ｓｒ、Ｍｇ、Ｎｉなどの多価金属が挙げられるが、これらに限られない。また、カルボン酸基およびスルホン酸基と塩を形成する有機アミンとしては、例えば、（モノ、ジまたはトリ）アルキルアミン、置換または未置換のアルキルアミンなどが挙げられるが、これらに限られない。また、芳香環としてベンゼン環やナフタレン環が挙げられる。上記本発明の酸基導入色素における酸基としては、スルホン酸基またはその塩の基が特に好ましく、スルホン酸基の数は、１分子当たり１個が好ましい。 In the general formulas (1) to (7), examples of the optional substituent other than the carboxylic acid group and the sulfonic acid group include substituents such as a nitro group, a hydroxy group, an alkoxy group, an alkyl group, and a halogen group. However, it is not limited to these. Examples of the metal that forms a salt with the carboxylic acid group and the sulfonic acid group include alkali metals such as Li, Na, and K, and polyvalent metals such as Ca, Ba, Al, Mn, Sr, Mg, and Ni. However, it is not limited to these. Examples of organic amines that form salts with carboxylic acid groups and sulfonic acid groups include, but are not limited to, (mono, di, or tri) alkylamines, substituted or unsubstituted alkylamines, and the like. Moreover, a benzene ring and a naphthalene ring are mentioned as an aromatic ring. The acid group in the acid group-introduced dye of the present invention is particularly preferably a sulfonic acid group or a salt group thereof, and the number of sulfonic acid groups is preferably one per molecule.
本発明において使用される有機顔料としては、例えば、アゾ系顔料、フタロシアニン系顔料、キナクリドン系顔料、ペリレン・ペリノン系顔料、イソインドリノン系顔料、イソインドリン系顔料、ジオキサジン系顔料、キノフタロン系顔料、ジケトピロロピロール系顔料、アンスラキノン系顔料、チオインジゴ系顔料、金属錯体系顔料などが挙げられるが、これらに限られない。 Examples of the organic pigment used in the present invention include azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments, dioxazine pigments, quinophthalone pigments, Examples include, but are not limited to, diketopyrrolopyrrole pigments, anthraquinone pigments, thioindigo pigments, and metal complex pigments.
これらの有機顔料の中でも特にＣ．Ｉ．ピグメントレッド１２２、Ｃ．Ｉ．ピグメントレッド１７７、Ｃ．Ｉ．ピグメントレッド２５４およびＣ．Ｉ．ピグメントバイオレット１９から選ばれる少なくとも１種が好ましい。 Among these organic pigments, C.I. I. Pigment red 122, C.I. I. Pigment red 177, C.I. I. Pigment red 254 and C.I. I. At least one selected from pigment violet 19 is preferable.
また、本発明で用いられる有機顔料は、１次粒子径が１００ｎｍ以下であるか、微粒化処理により１次粒子径を１００ｎｍ以下にした有機顔料を用いることが、得られる着色物の透明性や鮮明性の向上という観点から好ましい。顔料の微粒化処理法としては、例えば、食塩の存在下でミル摩砕を行うソルトミリング法など（例えば、特開２００１−２２０５２０公報および特開２００１−２６４５２８公報）が挙げられるが、これらに限られない。 The organic pigment used in the present invention has a primary particle size of 100 nm or less, or an organic pigment having a primary particle size of 100 nm or less by atomization treatment, It is preferable from the viewpoint of improving the sharpness. Examples of the pigment atomization method include a salt milling method in which mill milling is performed in the presence of salt (for example, JP-A-2001-220520 and JP-A-2001-264528). I can't.
本発明の顔料組成物は、前記有機顔料と前記本発明の酸基導入色素とを従来公知の方法（例えば、特開２００１−２７１００４公報および特開２００４−９１４９７公報）により混合して製造することができ、例えば、前記有機顔料と前記本発明の酸基導入色素との粉末同士を混合する方法、水や溶解力のある有機溶媒に分散させた前記有機顔料と前記本発明の酸基導入色素とのサスペンジョン同士を混合する方法、有機顔料の製造工程中の任意の工程に前記本発明の酸基導入色素を加える方法などが挙げられるが、製造方法は特に限定されない。上記顔料製造工程中の任意の工程としては、例えば、ソルトミリングが挙げられるが、これに限られない。前記本発明の酸基導入色素を加える際の状態としては、粉末、ペースト、サスペンジョンの形態が挙げられるが、これに限られない。 The pigment composition of the present invention is produced by mixing the organic pigment and the acid group-introduced dye of the present invention by a conventionally known method (for example, JP-A Nos. 2001-271004 and 2004-91497). For example, a method of mixing powders of the organic pigment and the acid group-introducing dye of the present invention, the organic pigment dispersed in water or an organic solvent having solubility, and the acid group-introducing dye of the present invention And a method of mixing the suspensions with each other, a method of adding the acid group-introducing dye of the present invention to an arbitrary step in the production process of the organic pigment, and the like, but the production method is not particularly limited. As an arbitrary process in the said pigment manufacturing process, although salt milling is mentioned, for example, it is not restricted to this. Examples of the state when the acid group-introducing dye of the present invention is added include, but are not limited to, powder, paste, and suspension.
また、本発明の顔料組成物の配合割合は、有機顔料１００質量部に対して前記本発明の酸基導入色素が、０．１〜３０質量部の割合が好ましく、さらに好ましくは１〜２０質量部の割合である。前記本発明の酸基導入色素の配合割合が少なすぎると、目的とする効果が十分に得られにくくなる。また、前記の配合割合が多すぎても、それに比例した効果は得られず、顔料組成物およびそれを用いた着色組成物の諸物性を低下させ、本来の色相を大きく変化させてしまう要因になる。 The blending ratio of the pigment composition of the present invention is preferably such that the acid group-introduced dye of the present invention is 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight with respect to 100 parts by weight of the organic pigment. The ratio of parts. If the blending ratio of the acid group-introduced dye of the present invention is too small, the intended effect is not sufficiently obtained. Moreover, even if the blending ratio is too large, an effect proportional to the ratio cannot be obtained, and the various physical properties of the pigment composition and the coloring composition using the pigment composition are decreased, and the original hue is greatly changed. Become.
本発明において前記本発明の酸基導入色素が有機顔料に対して有用な働きをする理由としては以下の機構が考えられる。本発明に用いる前記本発明の酸基導入色素は分子骨格に芳香環を含有しているため、芳香環骨格を有する有機顔料表面にπ電子の相互作用により効果的に吸着すると考えられる。さらに、前記本発明の酸基導入色素の分子量が小さいことから、お互いの立体障害を抑えてより効率的に吸着できると考えられる。このとき前記本発明の酸基導入色素のスルホン酸基またはカルボン酸基などの極性基は、吸着した有機顔料表面に出て顔料表面の負の表面電位が増大し、静電気的反発力により初期の顔料分散性および経時の分散安定性が増大するためと考えられる。 In the present invention, the following mechanism can be considered as the reason why the acid group-introduced dye of the present invention has a useful function on the organic pigment. Since the acid group-introduced dye of the present invention used in the present invention contains an aromatic ring in the molecular skeleton, it is considered that the acid group-introduced dye is effectively adsorbed on the surface of the organic pigment having the aromatic ring skeleton by the interaction of π electrons. Furthermore, since the molecular weight of the acid group-introduced dye of the present invention is small, it is considered that the steric hindrance can be suppressed and adsorption can be performed more efficiently. At this time, polar groups such as a sulfonic acid group or a carboxylic acid group of the acid group-introduced dye of the present invention emerge on the surface of the adsorbed organic pigment, and the negative surface potential of the pigment surface increases. This is thought to be due to an increase in pigment dispersibility and dispersion stability over time.
前記本発明の酸基導入色素は、従来公知の分散剤、例えば、ロジン、高分子系分散剤、界面活性剤または極性基を導入した顔料誘導体などと併用することもできる。ロジンとしては、例えば、ロジン誘導体、ロジン変性マレイン樹脂、ロジン変性フェノール樹脂、ロジン変性フマル樹脂などが挙げられるが、これらに限られない。高分子系分散剤としては、例えば、市販されているＢＹＫ社のディスパビック１６０、１６１、１６２、１６３、１６４、１８２、１８４、アビシア社のソルスパース２２０００、２４０００、２８０００、楠本化成社のディスパロンＤＡ−２３４、３２５、３７５、７２５などが挙げられるが、これらに限られない。顔料誘導体としては、例えば、市販されているアビシア社のソルスパース５０００、２２００などが挙げられるが、これらに限られない。 The acid group-introduced dye of the present invention can be used in combination with a conventionally known dispersant, for example, rosin, a polymeric dispersant, a surfactant, or a pigment derivative having a polar group introduced. Examples of rosin include, but are not limited to, rosin derivatives, rosin-modified maleic resins, rosin-modified phenolic resins, rosin-modified fumarate resins, and the like. Examples of the polymeric dispersant include commercially available Dispavic 160, 161, 162, 163, 164, 182, and 184 from BYK, Solsperse 22000, 24000, and 28000 from Abycia, and Disparon DA- from Enomoto Kasei Co., Ltd. 234, 325, 375, 725, etc., but are not limited thereto. Examples of pigment derivatives include, but are not limited to, commercially available Solsperse 5000, 2200 manufactured by Avicia.
本発明の顔料組成物は、例えば、各種印刷インキ、サイジングカラー、バインダーカラーやコーティング剤、各種塗料、電子写真用乾式トナーまたは湿式トナー、熱転写記録用インキ、筆記具用インキ、カラーフィルター画素形成用塗布液、インクジェットインクなどの着色剤として利用できる。それらの中でも特に分散性、分散安定性、透明性および鮮明性の要求レベルが高いカラーフィルター画素形成用塗布液やインクジェットインク用に有用である。 The pigment composition of the present invention includes, for example, various printing inks, sizing colors, binder colors and coating agents, various paints, electrophotographic dry toners or wet toners, thermal transfer recording inks, writing instrument inks, and coatings for forming color filter pixels. It can be used as a colorant for liquids and inkjet inks. Among them, it is particularly useful for a coating solution for forming a color filter pixel and an ink-jet ink that have a high level of required dispersibility, dispersion stability, transparency, and sharpness.
一般に、カラーフィルター画素形成用塗布液は、顔料に、例えば、感光性ポリアクリレート系樹脂、感光性アクリル系樹脂、感光性ポリアミド系樹脂、感光性ポリイミド系樹脂など、或いは不飽和ポリエステル系樹脂などの感光性樹脂ワニス、またはこれらにさらに反応希釈剤としてモノマーまたはオリゴマーが加えられたワニス、光開始剤（必要に応じて増感剤とともに）、溶剤などを加えた後、高分散させて製造される。その際、上記顔料として本発明の顔料組成物を用いることで、分散性、分散安定性、透明性および鮮明性に優れたカラーフィルター画素形成用塗布液が得られる。 In general, the color filter pixel forming coating liquid is made of, for example, a photosensitive polyacrylate resin, a photosensitive acrylic resin, a photosensitive polyamide resin, a photosensitive polyimide resin, or an unsaturated polyester resin. Photosensitive resin varnishes, or varnishes in which monomers or oligomers are further added as reaction diluents to these, photoinitiators (with sensitizers if necessary), solvents, etc. are added and then highly dispersed. . At that time, by using the pigment composition of the present invention as the pigment, a coating solution for forming a color filter pixel excellent in dispersibility, dispersion stability, transparency and sharpness can be obtained.
上記モノマーまたはオリゴマーとしては、例えば、（メタ）アクリル酸エステル、（メタ）アクリル酸、（メタ）アクリルアミド、酢酸ビニル、スチレン、（メタ）アクリロニトリル、（メタ）アクリレートオリゴマーなどが挙げられるが、これらに限られない。上記光開始剤としては、例えば、アセトフェノン系、ベンゾイン系、ベンゾフェノン系、チオキサントン系、トリアジン系、カルバゾール系、イミダゾール系などが挙げられるが、これらに限られない。上記増感剤としては、例えば、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、キノン系、アンスラキノン系、イソフタロフェノン系、エステル系、ベンジル系、ベンゾフェノン系などが挙げられるが、これらに限られない。溶剤としては、例えば、（ポリ）アルキレングリコールモノアルキルエーテル、（ポリ）アルキレングリコールモノアルキルエーテルアセテート、エーテル、ケトン、乳酸アルキルエステル、エステル、芳香族炭化水素、アミドなどが挙げられるが、これらに限られない。 Examples of the monomer or oligomer include (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, (meth) acrylate oligomer, and the like. Not limited. Examples of the photoinitiator include, but are not limited to, acetophenone series, benzoin series, benzophenone series, thioxanthone series, triazine series, carbazole series, and imidazole series. Examples of the sensitizer include, but are not limited to, acylphosphine oxide, methylphenylglyoxylate, quinone, anthraquinone, isophthalophenone, ester, benzyl, and benzophenone. Absent. Examples of the solvent include (poly) alkylene glycol monoalkyl ether, (poly) alkylene glycol monoalkyl ether acetate, ether, ketone, alkyl lactate ester, ester, aromatic hydrocarbon, amide, and the like. I can't.
一般に、インクジェットインクは、顔料に、例えば、水、水溶性樹脂や界面活性剤および水溶性溶剤などを加えて構成され、さらに保存性、吐出安定性などを向上させる目的で、表面張力調整剤、粘度調整剤、比抵抗調整剤、消泡剤、防黴剤などを加えた後、高分散させて製造される。その際、上記顔料として本発明の顔料組成物を用いることで、分散性、分散安定性および透明性や鮮明性に優れたインクジェットインクが得られる。 In general, an inkjet ink is composed of a pigment, for example, water, a water-soluble resin, a surfactant, a water-soluble solvent, and the like, and for the purpose of further improving storage stability, ejection stability, and the like, After adding a viscosity modifier, a specific resistance modifier, an antifoaming agent, an antifungal agent, etc., it is manufactured by highly dispersing. At that time, by using the pigment composition of the present invention as the pigment, an inkjet ink excellent in dispersibility, dispersion stability, transparency and sharpness can be obtained.
上記水溶性樹脂としては、例えば、アクリル系、アクリル−スチレン系、ポリエステル系、ポリアミド系、ポリウレタン系樹脂などが挙げられるが、これらに限られない。上記界面活性剤としては、例えば、アニオン系、非イオン系、両性系、カチオン系などの界面活性剤などが挙げられるが、これらに限られない。上記水溶性溶剤としては、例えば、アルコール、多価アルコール、多価アルコールエーテル、アミン、複素環、スルホキシド、スルホン、アセトニトリルなどが挙げられるが、これらに限られない。 Examples of the water-soluble resin include, but are not limited to, acrylic, acrylic-styrene, polyester, polyamide, and polyurethane resins. Examples of the surfactant include, but are not limited to, anionic, nonionic, amphoteric, and cationic surfactants. Examples of the water-soluble solvent include, but are not limited to, alcohol, polyhydric alcohol, polyhydric alcohol ether, amine, heterocycle, sulfoxide, sulfone, and acetonitrile.
次に、合成例、実施例および比較例を挙げて本発明をさらに具体的に説明するが、本発明はこれらに限定されるものではない。なお、文中「部」とあるのは質量基準である。 Next, although a synthesis example, an Example, and a comparative example are given and this invention is demonstrated further more concretely, this invention is not limited to these. In the text, “part” is based on mass.
酸基導入色素の合成例
ジアゾ成分として２−アミノ−４−メチル−５−クロロベンゼンスルホン酸２０．５部と、カップラー成分として２−ヒドロキシ−３−フェニルカルバモイルナフタレン２７．０部とを公知の方法により反応させて下記表１に記載の酸基導入色素Ａを４５．０部得た。
Synthesis Example of Acid Group-Introducing Dye 20.5 parts of 2-amino-4-methyl-5-chlorobenzenesulfonic acid as diazo component and 27.0 parts of 2-hydroxy-3-phenylcarbamoylnaphthalene as coupler component are known methods To obtain 45.0 parts of acid group-introduced dye A described in Table 1 below.
ジアゾ成分およびカップラー成分を変えた他は酸基導入色素Ａの合成例に従って同様に反応させて下記表１の酸基導入色素Ｂ〜酸基導入色素Ｊを得た。 Except that the diazo component and coupler component were changed, the reaction was carried out in the same manner according to the synthesis example of acid group-introduced dye A to obtain acid group-introduced dye B to acid group-introduced dye J in Table 1 below.
以上の合成結果の一覧を表１に示した。
［顔料組成物の実施例］
参考例１
Ｃ．Ｉ．ピグメントレッド２５４の顔料２０部を含む水性サスペンジョンに、酸基導入色素Ａの３部を含む水性サスペンジョンを加えた。混合液を３０分間攪拌した後、混合液をろ過、水洗し、取り出した顔料ペーストを一昼夜乾燥させ、粉砕し、目的の顔料組成物２１部を得た。
[Examples of pigment composition]
Reference example 1
C. I. An aqueous suspension containing 3 parts of acid group-introduced dye A was added to an aqueous suspension containing 20 parts of Pigment Red 254 pigment. After stirring the mixed solution for 30 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 21 parts of the target pigment composition.
参考例２
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｂを用いて、参考例１と同様の方法で行った。
参考例３
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｃを用いて、参考例１と同様の方法で行った。
Reference example 2
With acid group-introduced dye B instead of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference example 3
With acid group-introduced dye C instead of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
参考例４
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｄを用いて、参考例１と同様の方法で行った。
参考例５
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｅを用いて、参考例１と同様の方法で行った。
Reference example 4
With acid group-introduced dye D in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference Example 5
With acid group-introduced dye E in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
参考例６
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｆを用いて、参考例１と同様の方法で行った。
参考例７
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｇを用いて、参考例１と同様の方法で行った。
Reference Example 6
With acid group-introduced dye F in place of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Reference Example 7
With acid group-introduced dye G in place of the acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
参考例８
参考例１の酸基導入色素Ａの代わりに酸基導入色素Ｈを用いて、参考例１と同様の方法で行った。
比較例１
参考例１で使用した酸基導入色素Ａは添加せずに同様の操作を行い未処理顔料を得た。
Reference Example 8
With acid group-introduced dye H in place of acid group-introduced dye A of Reference Example 1 was conducted in the same manner as in Reference Example 1.
Comparative Example 1
The same operation was performed without adding the acid group-introduced dye A used in Reference Example 1 to obtain an untreated pigment.
参考例９
Ｃ．Ｉ．ピグメントレッド１７７の顔料３５部を含む水性サスペンジョンに、酸基導入色素Ｈの３．５部を含む水性サスペンジョンを加えた。混合液を３０分間攪拌した後、混合液をろ過、水洗し、取り出した顔料ペーストを一昼夜乾燥させ、粉砕し、目的の顔料組成物３６部を得た。
Reference Example 9
C. I. An aqueous suspension containing 3.5 parts of acid group-introduced dye H was added to an aqueous suspension containing 35 parts of Pigment Red 177 pigment. After stirring the mixed solution for 30 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 36 parts of the target pigment composition.
実施例１０
参考例９の酸基導入色素Ｈの代わりに酸基導入色素Ｉを用いて、参考例９と同様の方法で行った。
実施例１１
参考例９の酸基導入色素Ｈの代わりに酸基導入色素Ｊを用いて、参考例９と同様の方法で行った。
比較例２
参考例９で使用した酸基導入色素Ｈは添加せずに同様の操作を行い未処理顔料を得た。
Example 10
With acid group-introduced dye I in place of the acid group-introduced dye H of Example 9 was carried out in the same manner as in Reference Example 9.
Example 11
With acid group-introduced dye J instead of acid group-introduced dye H of Example 9 was carried out in the same manner as in Reference Example 9.
Comparative Example 2
The same operation was performed without adding the acid group-introduced dye H used in Reference Example 9 to obtain an untreated pigment.
［カラーフィルター画素形成用塗布液の調製、試験および評価］
参考例１〜９、実施例１０、１１で調製した顔料組成物、および比較例１、２で調製した未処理顔料を用い、以下のようにしてカラーフィルター画素形成用塗布液を調製し、粘度、保存安定性および明彩度性の試験を行った。
[Preparation, test and evaluation of coating solution for forming color filter pixels]
Using the pigment compositions prepared in Reference Examples 1 to 9, Examples 10 and 11, and the untreated pigment prepared in Comparative Examples 1 and 2, a color filter pixel forming coating solution was prepared as follows, and the viscosity Then, storage stability and lightness were tested.
［カラーフィルター画素形成用塗布液の調製］
参考例１２
２５０ｍｌガラスビンにジルコニアビーズ１８０部を入れた後、参考例１で調製した顔料組成物、アクリル系樹脂、高分子系分散剤、およびプロピレングリコールモノアセテート（ＰＧＭ−Ａｃ）を加え、プレミキシングで簡単に混ぜた後、ペイントコンディショナーを用いて３時間分散させて分散液１００．０部を得た。その後、２５０ｍｌガラスビンに先ほど得られた分散液、アクリル系樹脂、ジペンタエリスリトールヘキサアクリレート、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）ブタノン−１、２，４−ジエチルチオキサントン、およびＰＧＭ−Ａｃを加え、十分攪拌した後、メンブレンフィルターで濾過を行いカラーフィルター画素形成用塗布液１５０．０部を得た（詳細の配合は下記表を参照）。
[Preparation of coating solution for forming color filter pixels]
Reference Example 12
After putting 180 parts of zirconia beads in a 250 ml glass bottle, add the pigment composition prepared in Reference Example 1, an acrylic resin, a polymer dispersant, and propylene glycol monoacetate (PGM-Ac), and easily by premixing. After mixing, the mixture was dispersed for 3 hours using a paint conditioner to obtain 100.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, acrylic resin, dipentaerythritol hexaacrylate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2,4-diethylthioxanthone, And PGM-Ac were added and sufficiently stirred, followed by filtration through a membrane filter to obtain 150.0 parts of a color filter pixel forming coating solution (see the table below for details of the composition).
参考例１３
参考例１で調製した顔料組成物の代わりに参考例２で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
参考例１４
参考例１で調製した顔料組成物の代わりに参考例３で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
参考例１５
参考例１で調製した顔料組成物の代わりに参考例４で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
Reference Example 13
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 2 instead of the pigment composition prepared in Reference Example 1.
Reference Example 14
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 3 instead of the pigment composition prepared in Reference Example 1.
Reference Example 15
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 4 instead of the pigment composition prepared in Reference Example 1.
参考例１６
参考例１で調製した顔料組成物の代わりに参考例５で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
参考例１７
参考例１で調製した顔料組成物の代わりに参考例６で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
実施例１８
参考例１で調製した顔料組成物の代わりに参考例７で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
Reference Example 16
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 5 instead of the pigment composition prepared in Reference Example 1.
Reference Example 17
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 6 instead of the pigment composition prepared in Reference Example 1.
Example 18
The same procedure as in Reference Example 12 was performed using the pigment composition prepared in Reference Example 7 instead of the pigment composition prepared in Reference Example 1.
参考例１９
参考例１で調製した顔料組成物の代わりに参考例８で調製した顔料組成物を用いて、参考例１２と同様の方法で行った。
比較例３
参考例１で調製した顔料組成物の代わりに比較例１で調製した未処理顔料を用いて、参考例１２と同様の方法で行った。
Reference Example 19
Using the pigment composition prepared in Reference Example 8 instead of the pigment composition prepared in Reference Example 1, the same procedure as in Reference Example 12 was performed.
Comparative Example 3
Using the untreated pigment prepared in Comparative Example 1 instead of the pigment composition prepared in Reference Example 1, the same procedure as in Reference Example 12 was performed.
参考例２０
２５０ｍｌガラスビンにジルコニアビーズ２００部を入れた後、参考例９で調製した顔料組成物、アクリル系樹脂、高分子系分散剤、およびＰＧＭ−Ａｃを加えプレミキシングで簡単に混ぜた後、ペイントコンディショナーを用いて３時間分散させて分散液１００．０部を得た。その後、２５０ｍｌガラスビンに先ほど得られた分散液、アクリル系樹脂、ジペンタエリスリトールヘキサアクリレート、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）ブタノン−１、２，４−ジエチルチオキサントン、およびＰＧＭ−Ａｃを加え十分攪拌した後、メンブレンフィルターで濾過を行い、カラーフィルター画素形成用塗布液を１５０．０部得た（詳細の配合は下記表を参照）。
Reference Example 20
After adding 200 parts of zirconia beads in a 250 ml glass bottle, add the pigment composition prepared in Reference Example 9, acrylic resin, polymer dispersant, and PGM-Ac, and mix them easily by premixing. And dispersed for 3 hours to obtain 100.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, acrylic resin, dipentaerythritol hexaacrylate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2,4-diethylthioxanthone, And PGM-Ac were added and sufficiently stirred, followed by filtration with a membrane filter to obtain 150.0 parts of a color filter pixel forming coating solution (see the table below for details).
実施例２１
参考例９で調製した顔料組成物の代わりに実施例１０で調製した顔料組成物を用いて、参考例２０と同様の方法で行った。
実施例２２
参考例９で調製した顔料組成物の代わりに実施例１１で調製した顔料組成物を用いて、参考例２０と同様の方法で行った。
比較例４
参考例９で調製した顔料組成物の代わりに比較例２で調製した未処理顔料を用いて、参考例２０と同様の方法で行った。
Example 21
Using the pigment composition prepared in Example 10 instead of the pigment composition prepared in Reference Example 9, the same procedure as in Reference Example 20 was performed.
Example 22
Using the pigment composition prepared in Example 11 instead of the pigment composition prepared in Reference Example 9, the same procedure as in Reference Example 20 was performed.
Comparative Example 4
The same process as in Reference Example 20 was performed using the untreated pigment prepared in Comparative Example 2 instead of the pigment composition prepared in Reference Example 9.
［カラーフィルター画素形成用塗布液の試験および評価］
＜粘度および保存安定性＞
参考例１２〜２０、実施例２１、２２、および比較例３、４で得られたカラーフィルター画素形成用塗布液を２５℃中にて一時間静置した。その後、Ｂ型粘度計（（株）トキメック製、商品名：ＢＬ型、３０ｒｐｍ値）を用いて粘度を測定し、この測定値を初期粘度とした。次に、初期粘度を測定後、その試料を２５℃中にて１週間保持した後、初期粘度の測定と同様にして経時粘度を測定し、保存安定性の判定として、保存安定性に全く問題ないレベルを◎、使用可能なレベルを○、増粘のため使用にやや難があるレベルを△、著しい増粘のため使用不可能なレベルを×の四段階の評価とした。
[Testing and evaluation of coating solution for forming color filter pixels]
<Viscosity and storage stability>
Reference Example 12-20 and allowed to stand for one hour in Example 21, 22, and Comparative Examples 3 and 4 obtained in 25 ° C. in a color filter pixel-forming coating liquid. Thereafter, the viscosity was measured using a B-type viscometer (trade name: BL type, 30 rpm value, manufactured by Tokimec Co., Ltd.), and this measured value was taken as the initial viscosity. Next, after measuring the initial viscosity, the sample was held at 25 ° C. for 1 week, and then the viscosity with time was measured in the same manner as the measurement of the initial viscosity. There were four levels of evaluation: ◎ for no level, ◯ for usable level, △ for somewhat difficult use due to thickening, and x for unusable level for significant thickening.
＜明彩度性＞
参考例１２〜２０、実施例２１、２２、および比較例３、４で得られたカラーフィルター画素形成用塗布液をスピンコータ（ＡＢＬＥ社製）にセットしたガラス板上の中心に適量滴下させ、ガラス板上にカラーフィルター画素形成用塗布液をコーティングした。その後でプレベイクを行った。作成したガラスを分光色彩計（ミノルタ（株）製、商品名：ＣＭ−３６００ｄ（型））を用いて標準光源Ｃ、縦視野角２度で色度を測定し、ＣＩＥ標準表色系の（Ｙ、ｘ、ｙ）を求めてコントラストを測定した。比較例３および４の数値をそれぞれ１００％として実施例の数値を換算し、コントラストを算出した。
<Brightness>
Reference Example 12-20, Example 21, 22, and Comparative (manufactured by ABLE Corporation) spin coater obtained color filter pixel-forming coating liquid in Examples 3 and 4 is dropped onto the center of the glass plate was set in a glass A coating solution for forming color filter pixels was coated on the plate. After that, pre-baking was performed. Using the spectrocolorimeter (Minolta Co., Ltd., trade name: CM-3600d (type)), the chromaticity of the prepared glass was measured with a standard light source C and a vertical viewing angle of 2 degrees. Y, x, y) were determined and the contrast was measured. The numerical values of Comparative Examples 3 and 4 were each set to 100%, and the numerical values of the Examples were converted to calculate the contrast.
以上の試験結果を表２および表３に示した。
表２および表３にて本発明の酸基導入色素を添加したものと添加していないものの評価結果を表しているが、本発明の酸基導入色素を用いたカラーフィルター画素形成用塗布液は、本発明の酸基導入色素を用いないカラーフィルター画素形成用塗布液に比べ、初期粘度が下がっていた。また、経時の粘度変化も殆ど見られず、保存安定性に優れていた。さらにコントラストの値では比較例３のコントラストに対して１０〜３０％程度上昇し、比較例４のコントラストに対しては２０％程度上昇していた。 Tables 2 and 3 show the evaluation results of the addition and non-addition of the acid group-introduced dye of the present invention. The coating solution for forming a color filter pixel using the acid group-introduced dye of the present invention is as follows. The initial viscosity was lower than that of the coating solution for forming a color filter pixel without using the acid group-introducing dye of the present invention. Further, almost no change in viscosity over time was observed, and the storage stability was excellent. Furthermore, the contrast value increased about 10 to 30% with respect to the contrast of Comparative Example 3, and increased about 20% with respect to the contrast of Comparative Example 4.
［顔料組成物の実施例］
参考例２３
Ｃ．Ｉ．ピグメントレッド１２２の顔料３０部を含む水性サスペンジョンに、酸基導入色素Ａ １．５部を含む水性サスペンジョンを加えた。混合液を１５分間攪拌した後、混合液をろ過、水洗し、取り出した顔料ペーストを一昼夜乾燥させ、粉砕し、目的の顔料組成物２７部を得た。
比較例５
参考例２３で使用した酸基導入色素Ａは添加せずに同様の操作を行い未処理顔料を得た。
[Examples of pigment composition]
Reference Example 23
C. I. An aqueous suspension containing 1.5 parts of acid group-introduced dye A was added to an aqueous suspension containing 30 parts of Pigment Red 122 pigment. After stirring the mixed solution for 15 minutes, the mixed solution was filtered and washed with water, and the taken out pigment paste was dried overnight and pulverized to obtain 27 parts of the intended pigment composition.
Comparative Example 5
The same operation was performed without adding the acid group-introduced dye A used in Reference Example 23 to obtain an untreated pigment.
［インクジェットインクの調製、試験および評価］
参考例２３で調製した顔料組成物、および比較例５で調製した未処理顔料を用い、以下のようにしてインクジェットインクを調製し、分散粒径、粘度、保存安定性、明彩度性の試験を行った。
[Preparation, testing and evaluation of inkjet ink]
Using the pigment composition prepared in Reference Example 23 and the untreated pigment prepared in Comparative Example 5, an ink-jet ink was prepared as follows, and the dispersion particle size, viscosity, storage stability, and color saturation were tested. Went.
［インクジェットインクの調製］
参考例２４
２５０ｍｌガラスビンにジルコニアビーズ１２０部を入れた後、参考例２３で調製した顔料組成物、水溶性スチレンアクリル系樹脂およびイオン交換水を加えプレミキシングで簡単に混ぜた後、ペイントコンディショナーを用いて５時間分散させて分散液６０．０部を得た。その後、２５０ｍｌガラスビンに先ほど得られた分散液、トリエチレングリコールモノブチルエーテル、グリセリン、サーフィノール、イオン交換水、メタノールおよび１０％グリセリル化キトサン（脱アセチル化度８０％、グリセリル置換度１．１）水溶液を加え、十分攪拌した後、ポアサイズ５ミクロンのメンブレンフィルターで濾過を行い、インクジェットインク１００．０部を得た（詳細の配合は下記表を参照）。
[Preparation of inkjet ink]
Reference Example 24
After adding 120 parts of zirconia beads in a 250 ml glass bottle, the pigment composition prepared in Reference Example 23, a water-soluble styrene acrylic resin, and ion-exchanged water were added and mixed briefly by premixing, and then for 5 hours using a paint conditioner. Dispersion was performed to obtain 60.0 parts of a dispersion. Thereafter, the dispersion obtained earlier in a 250 ml glass bottle, triethylene glycol monobutyl ether, glycerin, surfinol, ion-exchanged water, methanol and 10% glycerylated chitosan (deacetylation degree 80%, glyceryl substitution degree 1.1) aqueous solution The mixture was sufficiently stirred and filtered through a membrane filter having a pore size of 5 microns to obtain 100.0 parts of ink-jet ink (refer to the table below for details).
比較例６
参考例２３で調製した顔料組成物の代わりに比較例５で調製した未処理顔料を用いて、参考例２４と同様の方法で行った。
Comparative Example 6
Using the untreated pigment prepared in Comparative Example 5 instead of the pigment composition prepared in Reference Example 23, the same procedure as in Reference Example 24 was performed.
［インクジェットインクの試験および評価］
＜分散粒径および粒径安定性＞
参考例２４および比較例６で得られたインクジェットインクを２５℃中にて一時間静置した。その後、レーザー散乱方式粒度分布計（ベックマンコールター社製、商品名：N5 Submicron Particle Size Analyzer）を用いてインクジェットインク中の顔料の平均粒径を測定し、この値を初期粒径とした。次にこのインクジェットインクを５０℃中にて１０日間保持した後、初期粒径の測定と同様にしてインク中の顔料の平均粒径を測定し、この値を経時粒径とした。粒径安定性の判定として、初期粒径（φ１）と経時粒径（φ２）の比（φ２／φ１）が１．５以下のものを○、１．５を超えるものを×と評価した。
[Test and evaluation of inkjet ink]
<Dispersed particle size and particle size stability>
The inkjet ink obtained in Reference Example 24 and Comparative Example 6 was allowed to stand at 25 ° C. for 1 hour. Then, the average particle diameter of the pigment in inkjet ink was measured using the laser scattering type particle size distribution analyzer (Beckman Coulter company make, brand name: N5 Submicron Particle Size Analyzer), and this value was made into the initial particle diameter. Next, this ink-jet ink was held at 50 ° C. for 10 days, and then the average particle diameter of the pigment in the ink was measured in the same manner as the measurement of the initial particle diameter. As the determination of the particle size stability, the case where the ratio (φ2 / φ1) of the initial particle size (φ1) to the time-lapsed particle size (φ2) was 1.5 or less was evaluated as “○”, and the case where the ratio exceeded 1.5 was evaluated as “x”.
＜粘度および保存安定性＞
参考例２４および比較例６で得られたインクジェットインクを２５℃中にて一時間静置した。その後、Ｅ型粘度計（（株）東京産業製、商品名：ＲＥ８０型、５０ｒｐｍ値）を用いて粘度を測定し、この測定値を初期粘度とした。次に、初期粘度を測定後、その試料を５０℃中にて１０日間保持した後、初期粘度の測定と同様にして粘度を測定し、経時粘度を測定し、保存安定性の判定として、初期粘度（η１）と経時粘度（η２）の比（η２／η１）が２．０以下のものを○、２．０を超えるものを×と評価した。
<Viscosity and storage stability>
The inkjet ink obtained in Reference Example 24 and Comparative Example 6 was allowed to stand at 25 ° C. for 1 hour. Thereafter, the viscosity was measured using an E-type viscometer (trade name: RE80 type, 50 rpm value, manufactured by Tokyo Sangyo Co., Ltd.), and this measured value was taken as the initial viscosity. Next, after measuring the initial viscosity, the sample was held at 50 ° C. for 10 days, then the viscosity was measured in the same manner as the measurement of the initial viscosity, the viscosity with time was measured, and the storage stability was determined as the initial value. The case where the ratio (η2 / η1) of the viscosity (η1) and the time-dependent viscosity (η2) was 2.0 or less was evaluated as ○, and the case where the ratio exceeded 2.0 was evaluated as ×.
＜色相および透明性＞
作成したインクジェットインクを隠蔽力試験紙（日本テストパネル工業（株））に、バーコーター規格６番で展色を行い、グロスメータ（ＢＹＫ社 ヘイズ・グロスメータ）にて６０度のグロスを測定した。また、透明性はインクジェットインクを市販インクジェット用ＯＨＰフィルムにバーコーター規格６番で展色を行い目視にて透明性評価を行った。評価は良好：○、半透明：△、透明性なし：×とした。
<Hue and transparency>
The prepared ink-jet ink was developed on a hiding power test paper (Nippon Test Panel Industry Co., Ltd.) with a bar coater standard No. 6, and a gloss of 60 degrees was measured with a gloss meter (BYK Hayes Gloss Meter). . In addition, the transparency was evaluated by visually developing the ink-jet ink on a commercially available OHP film for ink-jet printing according to bar coater standard No. 6. Evaluation was good: ○, translucent: Δ, no transparency: x.
以上の試験結果を表４、５に示した。
本発明の酸基導入色素を用いたインクジェットインクは、小さな初期粒径と経時変化の殆どない優れた経時粒径安定性を示した。流動性においても低い初期粘度と優れた経時粘度安定性を示している。また、従来品と比較して透明性に優れ、高いグロスを有していた。 The ink-jet ink using the acid group-introduced dye according to the present invention exhibited excellent initial particle size stability with little initial particle size and little change with time. In terms of fluidity, it exhibits a low initial viscosity and excellent viscosity stability over time. Moreover, it was excellent in transparency compared with the conventional product and had high gloss.
本発明により、分散性、分散安定性および透明性や鮮明性に優れた着色組成物およびそれに用いられる顔料組成物を提供することができた。本発明の顔料組成物およびそれを用いた着色組成物は、例えば、各種印刷インキ、サイジングカラー、バインダーカラーやコーティング剤、各種塗料、電子写真用乾式トナーまたは湿式トナー、熱転写記録用インキ、筆記具用インキ、カラーフィルター画素形成用塗布液用、インクジェットインク用などに利用することができる。それらの中でも特に分散性、分散安定性および透明性や鮮明性の要求レベルが高いカラーフィルター画素形成用塗布液用やインクジェットインク用に有用である。 According to the present invention, it was possible to provide a coloring composition excellent in dispersibility, dispersion stability, transparency and sharpness, and a pigment composition used therefor. The pigment composition of the present invention and the coloring composition using the same are, for example, various printing inks, sizing colors, binder colors and coating agents, various paints, electrophotographic dry toners or wet toners, thermal transfer recording inks, and writing instruments. It can be used for ink, coating liquid for forming color filter pixels, inkjet ink and the like. Among them, it is particularly useful for a coating solution for forming a color filter pixel and an ink-jet ink, which have high required levels of dispersibility, dispersion stability, transparency and sharpness.
Claims (7)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007233829A JP5173333B2 (en) | 2006-11-02 | 2007-09-10 | Pigment composition, coloring composition using the same, and color filter |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006298905 | 2006-11-02 | ||
| JP2006298905 | 2006-11-02 | ||
| JP2007016863 | 2007-01-26 | ||
| JP2007016863 | 2007-01-26 | ||
| JP2007233829A JP5173333B2 (en) | 2006-11-02 | 2007-09-10 | Pigment composition, coloring composition using the same, and color filter |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012226593A Division JP5461654B2 (en) | 2006-11-02 | 2012-10-12 | Color filter pixel forming coating solution and color filter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008202021A JP2008202021A (en) | 2008-09-04 |
| JP5173333B2 true JP5173333B2 (en) | 2013-04-03 |
Family
ID=39779841
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007233829A Active JP5173333B2 (en) | 2006-11-02 | 2007-09-10 | Pigment composition, coloring composition using the same, and color filter |
| JP2012226593A Active JP5461654B2 (en) | 2006-11-02 | 2012-10-12 | Color filter pixel forming coating solution and color filter |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012226593A Active JP5461654B2 (en) | 2006-11-02 | 2012-10-12 | Color filter pixel forming coating solution and color filter |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP5173333B2 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4994084B2 (en) * | 2007-03-30 | 2012-08-08 | 富士フイルム株式会社 | Ink-jet ink for color filter, color filter, method for producing the same, and display device |
| WO2009041312A1 (en) * | 2007-09-27 | 2009-04-02 | Sakata Inx Corp. | Pigment dispersion assistant, pigment dispersion containing the same, and use of the pigment dispersion |
| JP5442960B2 (en) * | 2008-05-21 | 2014-03-19 | サカタインクス株式会社 | Coloring composition for black matrix |
| US8828132B2 (en) | 2010-01-15 | 2014-09-09 | Fujifilm Corporation | Pigment composition, ink for inkjet recording, coloring composition for color filter, and color filter |
| JP5651389B2 (en) | 2010-06-30 | 2015-01-14 | 富士フイルム株式会社 | Pigment composition, ink for ink jet recording, coloring composition for color filter, and color filter |
| JP6062848B2 (en) * | 2013-12-24 | 2017-01-18 | 大日精化工業株式会社 | Pigment dispersant, pigment composition, and pigment colorant |
| JP2016160419A (en) * | 2015-03-05 | 2016-09-05 | 東洋インキＳｃホールディングス株式会社 | Nonaqueous inkjet ink |
| JP7107198B2 (en) * | 2018-12-07 | 2022-07-27 | 東洋インキＳｃホールディングス株式会社 | Pigment dispersant and pigment composition, coloring composition and color filter using the same |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56166266A (en) * | 1980-05-23 | 1981-12-21 | Toyo Ink Mfg Co Ltd | Dispersing method of pigment |
| JPS59227951A (en) * | 1983-06-10 | 1984-12-21 | Toyo Ink Mfg Co Ltd | Dispersant for pigment |
| JPH0819366B2 (en) * | 1987-12-01 | 1996-02-28 | 東洋インキ製造株式会社 | Color chip manufacturing method |
| TW416975B (en) * | 1996-10-11 | 2001-01-01 | Ueno Seiyaku Oyo Kenkyujo Kk | Naphthol derivatives and process |
| JP3756594B2 (en) * | 1996-11-20 | 2006-03-15 | 東洋インキ製造株式会社 | Coloring composition for color filter and color filter |
| JP4622016B2 (en) * | 1999-12-20 | 2011-02-02 | 東洋インキ製造株式会社 | Pigment dispersant, pigment composition and pigment dispersion |
| JP2002121460A (en) * | 2000-03-06 | 2002-04-23 | Toyo Ink Mfg Co Ltd | Water-based pigment dispersion and ink jet recording liquid |
| JP2002241638A (en) * | 2000-03-06 | 2002-08-28 | Toyo Ink Mfg Co Ltd | Water-based pigment dispersion and inkjet recording liquid |
| JP2003183260A (en) * | 2001-12-21 | 2003-07-03 | Fuji Photo Film Co Ltd | Benzimidazolone compound and pigment dispersing agent, pigment dispersion composition and color photosensitive composition comprising the same |
| EP1594923B1 (en) * | 2003-01-17 | 2011-06-15 | Cabot Corporation | Methods for preparing aqueous colored pigment dispersions, and inkjet ink compositions |
| DE10353127A1 (en) * | 2003-11-14 | 2005-06-09 | Clariant Gmbh | Pigment compositions of yellow disazo pigment and organic pigment |
| JP4432506B2 (en) * | 2004-01-23 | 2010-03-17 | Ｊｓｒ株式会社 | Radiation-sensitive composition for color filter and preparation method thereof, color filter and color liquid crystal display device |
| TWI392708B (en) * | 2005-04-19 | 2013-04-11 | Dainichiseika Color Chem | Pigment dispersants and their use |
-
2007
- 2007-09-10 JP JP2007233829A patent/JP5173333B2/en active Active
-
2012
- 2012-10-12 JP JP2012226593A patent/JP5461654B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008202021A (en) | 2008-09-04 |
| JP5461654B2 (en) | 2014-04-02 |
| JP2013065021A (en) | 2013-04-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5461654B2 (en) | Color filter pixel forming coating solution and color filter | |
| TWI415907B (en) | Pigment compositions, colored compositions making use of the pigment compositions, and color filters | |
| JP5010229B2 (en) | Pigment dispersant, pigment composition, pigment colorant and coating solution for color filter | |
| JP5478691B2 (en) | Color filter pixel forming coating solution and color filter | |
| JP4476417B2 (en) | Red color resist ink and color filter | |
| JP5035718B2 (en) | Pigment dispersant and use thereof | |
| JP2009029886A (en) | Pigment dispersant, pigment composition, pigment coloring agent, and coloring agent for color filter | |
| JP2013047336A (en) | Pigment dispersion, and resist composition for color filter and ink composition each using the pigment dispersion | |
| JP2018528988A (en) | Use of novel naphthol AS pigment mixtures in printing materials | |
| JP5180939B2 (en) | Red color resist ink and pigment dispersion | |
| TW201627416A (en) | Pigment composition, coloring composition and method of producing pigment composition | |
| JP5139707B2 (en) | Pigment dispersant, pigment composition and pigment colorant | |
| JP6670771B2 (en) | Pigment dispersant, pigment composition, and pigment colorant | |
| JP5801976B1 (en) | Method for producing pigment composition | |
| JP5823432B2 (en) | Pigment dispersant, pigment composition, and pigment colorant | |
| JP5715928B2 (en) | Pigment dispersant, pigment composition and pigment colorant | |
| JP5823431B2 (en) | Pigment dispersant, pigment composition, and pigment colorant | |
| JP5705754B2 (en) | Pigment dispersant, pigment composition, and pigment colorant | |
| JP5952228B2 (en) | Pigment colorant | |
| JP2023134180A (en) | Pigment dispersion liquid and coating agent | |
| JP2012107157A (en) | Pigment dispersant, and pigment composition containing the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20100122 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120814 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20121012 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20121225 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121227 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 5173333 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |