JP5139707B2 - 顔料分散剤、顔料組成物および顔料着色剤 - Google Patents
顔料分散剤、顔料組成物および顔料着色剤 Download PDFInfo
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- JP5139707B2 JP5139707B2 JP2007091874A JP2007091874A JP5139707B2 JP 5139707 B2 JP5139707 B2 JP 5139707B2 JP 2007091874 A JP2007091874 A JP 2007091874A JP 2007091874 A JP2007091874 A JP 2007091874A JP 5139707 B2 JP5139707 B2 JP 5139707B2
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- pigment
- acid
- amino
- dispersant
- hydroxy
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- 239000000049 pigment Substances 0.000 title claims description 190
- 239000002270 dispersing agent Substances 0.000 title claims description 78
- 239000000203 mixture Substances 0.000 title claims description 46
- 239000003086 colorant Substances 0.000 title claims description 38
- 239000000976 ink Substances 0.000 claims description 38
- -1 amine salt Chemical class 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 239000003973 paint Substances 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 10
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Chemical group 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052742 iron Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 description 23
- 239000006185 dispersion Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 19
- 229920005989 resin Polymers 0.000 description 15
- 239000011347 resin Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 10
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical group 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 10
- 229920006317 cationic polymer Polymers 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- DIZBQMTZXOUFTD-UHFFFAOYSA-N 2-(furan-2-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CO1 DIZBQMTZXOUFTD-UHFFFAOYSA-N 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004070 electrodeposition Methods 0.000 description 3
- FCQJEPASRCXVCB-UHFFFAOYSA-N flavianic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FCQJEPASRCXVCB-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000003010 ionic group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 2
- MFGWMAAZYZSWMY-UHFFFAOYSA-N (2-naphthyl)methanol Chemical compound C1=CC=CC2=CC(CO)=CC=C21 MFGWMAAZYZSWMY-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- DFFMMDIDNCWQIV-UHFFFAOYSA-N 4-amino-3-methoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=CC=C1N DFFMMDIDNCWQIV-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- BVPJPRYNQHAOPQ-UHFFFAOYSA-N 4-nitronaphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=C([N+]([O-])=O)C2=C1 BVPJPRYNQHAOPQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 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
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000011268 mixed slurry Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
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- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical group C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
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- 229950000244 sulfanilic acid Drugs 0.000 description 2
- PBLNHHSDYFYZNC-UHFFFAOYSA-N (1-naphthyl)methanol Chemical compound C1=CC=C2C(CO)=CC=CC2=C1 PBLNHHSDYFYZNC-UHFFFAOYSA-N 0.000 description 1
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- VTYFKJMQQFAQJZ-UHFFFAOYSA-N 1-aminonaphthalene-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=C(S(O)(=O)=O)C=CC2=C1 VTYFKJMQQFAQJZ-UHFFFAOYSA-N 0.000 description 1
- QRTHCSOVSYURGO-UHFFFAOYSA-N 1-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=C(S(O)(=O)=O)C=CC2=C1 QRTHCSOVSYURGO-UHFFFAOYSA-N 0.000 description 1
- ONZWNZGVZFLMNZ-UHFFFAOYSA-N 1-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C([NH3+])=C(S([O-])(=O)=O)C=CC2=C1 ONZWNZGVZFLMNZ-UHFFFAOYSA-N 0.000 description 1
- XXEFGBKLROHLNO-UHFFFAOYSA-N 1-hydroxynaphthalene-2,3-disulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C(S(O)(=O)=O)=CC2=C1 XXEFGBKLROHLNO-UHFFFAOYSA-N 0.000 description 1
- SRZUCOADWCAQOD-UHFFFAOYSA-N 1-hydroxynaphthalene-2,6-disulfonic acid Chemical compound OC1=C(C=CC2=CC(=CC=C12)S(=O)(=O)O)S(=O)(=O)O SRZUCOADWCAQOD-UHFFFAOYSA-N 0.000 description 1
- JPWRLUYULZUVRH-UHFFFAOYSA-N 1-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 JPWRLUYULZUVRH-UHFFFAOYSA-N 0.000 description 1
- PWJNDVAKQLOWRZ-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 PWJNDVAKQLOWRZ-UHFFFAOYSA-N 0.000 description 1
- UNDUSVBXIVZGOQ-UHFFFAOYSA-N 1h-perimidin-2-amine Chemical compound C1=CC(NC(N)=N2)=C3C2=CC=CC3=C1 UNDUSVBXIVZGOQ-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- HVLJEMXDXOTWLV-UHFFFAOYSA-N 2,4-dichloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C(Cl)C=C(Cl)C2=C1 HVLJEMXDXOTWLV-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
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- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 1
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
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- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
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- GDPMGDWVWMWYNU-UHFFFAOYSA-N 2-aminonaphthalene-1,4-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC(S(O)(=O)=O)=C21 GDPMGDWVWMWYNU-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本発明の顔料分散剤は、ハロゲン化フタロシアニン化合物にスルホン酸基を導入した顔料誘導体であることに特徴があり、本発明の顔料分散剤は種々の顔料に対する優れた親和性を有しており、広範囲の顔料に使用可能である。また、本発明の顔料分散剤は優れた顔料分散効果を有していることより、種々の用途において使用される着色剤の製造に使用することができる。
(1)顔料と顔料分散剤とを予め公知の方法で混合し、得られた顔料組成物をビヒクルなどに添加してビヒクル中に分散させる、
(2)ビヒクルなどに顔料を分散させる際、ビヒクルなどに顔料と顔料分散剤を所定の割合で別々に添加してビヒクル中に分散させる、
(3)顔料と顔料分散剤をそれぞれビヒクルなどに別々に分散させた後、得られた各分散液を所定の割合で混合し、分散する、
(4)ビヒクルなどに顔料を分散させて得られた分散液に、顔料分散剤を所定の割合で添加して顔料を分散させる、
などの方法があり、いずれの方法においても目的とする顔料分散効果が得られる。さらに、上記(1)〜(4)の方法において、顔料分散剤のイオン性基のカウンターのイオン性基(対イオン性基)を有する重合体(高分子分散剤)を添加して分散させる方法が好ましい。より効果的には、上記(1)または(2)の方法で、さらに対イオン性基を有する重合体と併用する分散方法が望ましい。
実施例1
N−メチルピロリドン100部にPG36の20部、p−フェノールスルホン酸4.5部および炭酸カリウム17部を加え、180〜185℃で8時間撹拌する。冷却後、ろ過し、メタノール洗浄および水洗し、80℃で乾燥させて18.5部の下記顔料分散剤(A)を得た。
N−メチルピロリドン100部にPG36の20部、1−ナフトール3.7部および炭酸カリウム17部を加え、180〜185℃で8時間撹拌する。冷却後、ろ過し、メタノール洗浄および水洗し、80℃で乾燥させて18.5部の反応生成物を得た。この反応生成物10部を20%発煙硫酸50部に溶解し、20〜25℃で6時間反応させた。冷却後、反応混合物を氷水中に析出させ、ろ過および水洗し、下記顔料分散剤(B)のペースト56部(純量11部)を得た。このペーストを乾燥させ、元素分析により1分子あたり平均1個のスルホン酸基が導入されている顔料分散剤(B)11部を得た。
実施例1のp−フェノールスルホン酸の代わりにスルファニル酸を使用した以外は実施例1と同様にして下記顔料分散剤(C)18.5部を得た。
参考例2の1−ナフトールの代わりに1−ナフチルアミンを使用した以外は参考例2と同様にして下記顔料分散剤(D)11部を得た。
実施例1の顔料分散剤(A)のペースト90部(純量18部)に水240部を加え25℃で1時間攪拌した。これにテトラブチルアンモニウムクロライド7部を加え、1時間攪拌し、濾過、水洗および乾燥し、下記顔料分散剤(E)17部を得た。
実施例5において顔料分散剤(A)の代りに顔料分散剤(B)を使用した以外は、実施例5と同様にして下記顔料分散剤(F)18部を得た。
水1000部にPG36を19.0部加えて分散させ、スラリー化する。そこに、水50部に実施例1で得られた顔料分散剤(A)1.0部および苛性ソーダ0.1部を分散させてスラリー化したものを加える。その混合スラリーを70℃まで加熱し、pHを4〜5に調整する。20分間撹拌した後、濾過、乾燥、粉砕して、本発明の顔料組成物(1)を19.9部得た。
水1000部にPG36を19.0部加えて分散させ、スラリー化する。そこに、水50部に参考例2で得られた顔料分散剤(B)1.0部、テトラブチルアンモニウムクロライド0.9部および苛性ソーダ0.1部を分散させてスラリー化したものを加える。その混合スラリーを70℃まで加熱し、pHを4〜5に補正する。20分間撹拌した後、濾過、乾燥、粉砕して、顔料組成物(2)を20部得た。
顔料分散剤(A)の代わりに、実施例3で得られた顔料分散剤(C)を用いる以外は、実施例7と同様の操作を行なって、顔料組成物(3)を得た。
顔料分散剤(A)の代わりに、参考例4で得られた顔料分散剤(D)を用いる以外は、実施例7と同様の操作を行なって、顔料組成物(4)を得た。
顔料分散剤(A)の代わりに、実施例5で得られた顔料分散剤(E)を用いる以外は、実施例7と同様の操作を行なって、顔料組成物(5)を得た。
顔料分散剤(A)の代わりに、参考例6で得られた顔料分散剤(F)を用いる以外は、実施例7と同様の操作を行なって、顔料組成物(6)を得た。
それぞれ顔料組成物(1)、(3)、(5)を用い、顔料分散剤の効果を評価するために、下記配合(1)のカラーフィルター用着色剤を作製した(実施例13、15、17)。同様に、顔料組成物(2)、(4)、(6)を用い、下記配合(1)のカラーフィルター用着色剤を作製した(参考例14、16、18)。
配合(1)
・顔料組成物(1)〜(6)の何れか 20.0部
・ポリアクリル酸樹脂 30.0部
・シンナー 50.0部
上記配合成分を容器に入れ、ジルコニアビーズを加えてペイントコンディショナーにて分散させ、カラーフィルター用着色剤を作製した。
それぞれ顔料組成物(1)、(3)、(5)およびカチオン性高分子分散剤を用い、カチオン性高分子分散剤の併用の効果を評価するために、下記配合(2)のカラーフィルター用着色剤を作製した(実施例19、21、23)。同様に、顔料組成物(2)、(4)、(6)およびカチオン性高分子分散剤を用い、下記配合(1)のカラーフィルター用着色剤を作製した(参考例20、22、24)。
配合(2)
・顔料組成物(1)〜(6)の何れか 20.0部
・カチオン性高分子分散剤 4.0部
・ポリアクリル酸樹脂 30.0部
・シンナー 46.0部
上記配合成分を容器に入れ、ジルコニアビーズを加えてペイントコンディショナーにて分散させ、カラーフィルター用着色剤を作製した。
顔料組成物(1)20.0部の代わりに、PG36を20.0部用いること以外は、実施例19と同様の操作を行なって、顔料分散剤を添加していないカラーフィルター用着色剤を作製した。
<流動性(粘度変化)>
製造直後と25℃で7日後の実施例および比較例のカラーフィルター用着色剤の粘度(mPa・s)を、E型粘度計を用い、室温(25℃)、ローターの回転数6rpmの条件で測定した。
<グロス>
バーコーター(巻線の太さ0.45mm)を使用して、ポリプロピレンフィルムに展色し、展色面のグロスを目視およびグロスメーターにて比較した。なお、グロスの高いものを良好とし、評価結果を下記のように表示した。
○:良好
△:やや良好
×:不良
以上の結果を表1に示す。
Claims (6)
- 顔料と請求項1に記載の顔料分散剤とを含有してなることを特徴とする顔料組成物。
- 顔料分散剤の配合割合が、顔料100部に対して0.05〜40質量部である請求項2に記載の顔料組成物。
- 請求項2に記載の顔料組成物と皮膜形成材料とを含有してなることを特徴とする顔料着色剤。
- 画像表示用、画像記録用、印刷インキ用、筆記用インキ用、プラスチック用、顔料捺染用或いは塗料用である請求項4に記載の顔料着色剤。
- カラーフィルター用着色剤である請求項5に記載の顔料着色剤。
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