JP2005248127A - Pigment dispersant, pigment composition containing the same and pigment dispersion - Google Patents
Pigment dispersant, pigment composition containing the same and pigment dispersion Download PDFInfo
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- JP2005248127A JP2005248127A JP2004064265A JP2004064265A JP2005248127A JP 2005248127 A JP2005248127 A JP 2005248127A JP 2004064265 A JP2004064265 A JP 2004064265A JP 2004064265 A JP2004064265 A JP 2004064265A JP 2005248127 A JP2005248127 A JP 2005248127A
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- pigment
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- pigment dispersant
- dispersant
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- 239000000049 pigment Substances 0.000 title claims abstract description 169
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 62
- 239000006185 dispersion Substances 0.000 title claims abstract description 36
- 239000000203 mixture Substances 0.000 title claims description 27
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229920005989 resin Polymers 0.000 claims description 24
- 239000011347 resin Substances 0.000 claims description 24
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 9
- 239000002687 nonaqueous vehicle Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000008135 aqueous vehicle Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 abstract description 9
- 238000000576 coating method Methods 0.000 abstract description 9
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 26
- 239000003973 paint Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- -1 and the like Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- 125000000542 sulfonic acid group Chemical group 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 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 6
- 239000002966 varnish Substances 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 229920006284 nylon film Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 239000004923 Acrylic lacquer Substances 0.000 description 1
- 240000000972 Agathis dammara Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920002871 Dammar gum Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 235000003891 ferrous sulphate Nutrition 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
Description
本発明は使用適性、特に非集合性、非結晶性、及び流動性に優れた顔料分散剤に関するものであり、更に詳しくは、印刷インキまたは塗料に使用した場合の流動性、分散安定性ならびに乾燥皮膜にした場合の光沢等に優れる顔料分散剤、及びそれを含有する顔料組成物、並びに顔料分散体に関する。 The present invention relates to a pigment dispersant having excellent usability, particularly non-aggregability, non-crystallinity, and fluidity. More specifically, the present invention relates to fluidity, dispersion stability and drying when used in a printing ink or paint. The present invention relates to a pigment dispersant excellent in gloss and the like when formed into a film, a pigment composition containing the pigment dispersant, and a pigment dispersion.
印刷インキ、塗料等においては顔料を微細な状態で分散させることにより、印刷物または塗加工物の鮮明な色調、光沢等の適性を持たせている。また、顔料を安定な状態で分散させることにより印刷インキや塗料の流動性が向上し印刷適性が向上するばかりでなく、印刷インキや塗料を製造する際の労力やエネルギーを大きく削減することができる。さらに安定な状態の分散体は一般的に貯蔵安定性にも優れる。
しかしながら印刷インキや塗料に用いられる顔料はより鮮明な色調を実現するために微細な粒径であることが多く、そのために顔料粒子間の凝集力が強くなり上記のような適性を持たせることは困難であることが多い。
このような問題を解決するために、顔料分散剤を使用し、顔料とビヒクル間の親和性を良くし、分散体の安定化を図ることが知られており、これまでにも様々な顔料分散剤が開示されている。
例えば、特許文献１及び特許文献２に代表されるように有機顔料を母体骨格とし側鎖にスルホン酸、スルホンアミド基、アミノメチル基、フタルイミドメチル基等の置換基を導入して得られる化合物を混合する方法が知られているが、これらの化合物は顔料の非集合性、結晶安定性等に関する効果が大きいものの、染料に近い性質を有するため、顔料に比べ耐性が劣る場合があり、これらの化合物を含有する顔料組成物をインキや塗料に使用した時、経時等により化合物の色相が褪色し塗膜色相が変化する場合がある。また、塗膜形成後、ボイル、焼き付け等の高温処理や圧着により、これらの化合物が浮き出て色相の移行（マイグレーション）が生じることがあった。
また、特許文献３及び特許文献４には、これらの問題点を解決する手段として、顔料特有の着色がなく各種顔料に汎用性のあるトリアジン環含有塩基性化合物が開示されているが、これらの化合物はアクリル樹脂やアルキッド樹脂等の酸性官能基を有するバインダーでは効果を示すものの、ナフトール顔料及び縮合アゾ顔料に対しては十分な効果を示さなかった。また、ポリウレタン樹脂やポリアミド樹脂等の塩基性官能基を有するバインダーではほとんど効果を示さない。特にグラビアインキ等に使用される尿素結合を含む塩基性の高いポリウレタン樹脂には全く効果を示さなかった。
However, pigments used in printing inks and paints often have a fine particle size in order to achieve a clearer color tone. Often difficult.
In order to solve such problems, it is known to use a pigment dispersant, improve the affinity between the pigment and the vehicle, and stabilize the dispersion. Agents are disclosed.
For example, as represented by Patent Document 1 and Patent Document 2, a compound obtained by introducing an organic pigment as a base skeleton and introducing a substituent such as a sulfonic acid, a sulfonamide group, an aminomethyl group, or a phthalimidomethyl group into a side chain. Although a method of mixing is known, these compounds have a great effect on the non-aggregation property and crystal stability of the pigment, but have a property close to that of a dye. When a pigment composition containing a compound is used in an ink or paint, the hue of the compound may fade over time and the coating film hue may change. In addition, after the coating film is formed, these compounds may come out due to high-temperature treatment such as boiling or baking, or pressure bonding, and hue shift may occur.
In addition, Patent Document 3 and Patent Document 4 disclose triazine ring-containing basic compounds that do not have pigment-specific coloring and are versatile in various pigments as means for solving these problems. Although the compound showed an effect with a binder having an acidic functional group such as an acrylic resin or an alkyd resin, it did not show a sufficient effect on a naphthol pigment and a condensed azo pigment. In addition, a binder having a basic functional group such as a polyurethane resin or a polyamide resin has little effect. In particular, it was not effective at all with a highly basic polyurethane resin containing a urea bond used in gravure ink.
発明が解決しようとする課題は、印刷インキまたは塗料に使用した場合の流動性、分散安定性ならびに乾燥皮膜にした場合の光沢等に優れる、とりわけナフトール顔料及び縮合アゾ顔料に有効な顔料分散剤、及びそれを含有する顔料組成物、並びに顔料分散体を提供することにある。 The problem to be solved by the invention is a pigment dispersant which is excellent in fluidity, dispersion stability when used in printing inks or paints, and gloss when made into a dry film, particularly effective for naphthol pigments and condensed azo pigments, And a pigment composition containing the same, and a pigment dispersion.
上記課題に鑑み鋭意研究の結果、本発明者は、縮合アゾ顔料にスルホン酸を導入し、その金属塩が、前記の種々の問題点を改良し、良好に顔料を分散することができることを発見し、本発明を完成するに至った。すなわち、第１の発明は、下記一般式（１）で示される顔料分散剤である。
一般式（１）
As a result of diligent research in view of the above problems, the present inventors have discovered that a sulfonic acid is introduced into a condensed azo pigment, and that the metal salt can improve the above-mentioned various problems and disperse the pigment satisfactorily. Thus, the present invention has been completed. That is, the first invention is a pigment dispersant represented by the following general formula (1).
General formula (1)
また、第２及び第３の発明は、ナフトール顔料、縮合アゾ顔料から選ばれる少なくとも１種の顔料、第１の発明の顔料分散剤及び場合によっては重量平均分子量１０００〜１０００００の樹脂型顔料分散剤からなる顔料組成物である。
さらに、第４の発明は、第２及び第３の発明の顔料組成物を非水性または水性ビヒクルに分散してなる顔料分散体である。
さらに、第５の発明は、第４の発明の顔料分散体を含有する印刷インキである。
Further, the second and third inventions are at least one pigment selected from naphthol pigments and condensed azo pigments, the pigment dispersant of the first invention, and in some cases, a resin-type pigment dispersant having a weight average molecular weight of 1,000 to 100,000. A pigment composition comprising:
Furthermore, the fourth invention is a pigment dispersion obtained by dispersing the pigment compositions of the second and third inventions in a non-aqueous or aqueous vehicle.
Furthermore, the fifth invention is a printing ink containing the pigment dispersion of the fourth invention.
本発明の顔料分散剤を使用することにより、非集合性、非結晶性、流動性に優れるだけでなく、塗膜の光沢、色相に優れたインキ及び塗料を得ることが可能となる。 By using the pigment dispersant of the present invention, it is possible to obtain inks and paints that are not only excellent in non-aggregability, non-crystallinity, and fluidity but also excellent in gloss and hue of the coating film.
以下、本発明を詳細に説明する。
本発明の顔料分散剤は、縮合アゾ顔料にスルホン酸を導入し、そのスルホン酸を金属塩としたものである。
本発明の顔料分散剤の合成に使用する縮合アゾ顔料としては、具体的な例をカラーインデックスのジェネリックネームで示すと、ピグメントレッド１４４、１６６、２１４、２２０、２２１、２４２、２４８、２６２、ピグメントブラウン２３、４２等があげられる。
一般式（１）の式中Ｍは２価または３価の金属の一当量を表し、例えば、カルシウム、バリウム、マグネシウム、鉄、アルミニウム、ニッケル、コバルト、ストロンチウム等が挙げられる。
スルホン酸の置換基数は１〜３個であり、それぞれ混在していても構わない。スルホン酸の置換基数が４個以上であると、十分な効果が得られないだけではなく、マイグレーション性が悪化する。スルホン酸の置換基数を平均置換基数で表す場合があるが、平均置換基数としては１〜２個が好ましい。
本発明の顔料分散剤の製造方法は、一例として次のようである。
まず、濃硫酸に上記縮合アゾ顔料を溶解し、常温若しくは加熱してスルホン化を行い、次いで、十分な量の氷水中にその硫酸溶液を注入した懸濁液を濾過、水洗し、スルホン化されたプレスケーキを得る。
一般式（１）で表される金属塩化合物は、前記の操作で得られたプレスケーキを水または有機溶剤でリスラリーし、等モル強の金属の塩酸塩、硫酸塩、硝酸塩等の粉末または水溶液を添加し、撹拌後、濾過、水洗、乾燥して得ることができる。
本発明で得られる顔料分散剤は、通常、印刷インキまたは塗料に用いられる各種顔料に効果を発揮するが、とりわけ、ナフトール顔料及び縮合アゾ顔料に優れた効果を発揮する。ナフトール顔料としては、具体的な例をカラーインデックスのジェネリックネームで示すと、ピグメントレッド２、３、５、７、９、１２、１４、２２、２３、３１、１１２、１４６、１７０、１７１、１７５、１７６、１８５、ピグメントオレンジ５、２４、３８、ピグメントブラウン２５、ピグメントバイオレット３２等があげられる。また、縮合アゾ顔料としては、具体的な例をカラーインデックスのジェネリックネームで示すと、ピグメントレッド１４４、１６６、２１４、２２０、２２１、２４２、２４８、２６２、ピグメントオレンジ３１、ピグメントブラウン２３、４１、４２等があげられる。
本発明の顔料組成物は、顔料に一般式（１）で表される顔料分散剤を単独で添加するか、樹脂型顔料分散剤を併用して添加したものである。
本発明の顔料組成物に用いられる樹脂型顔料分散剤は、ポリエステル系、アクリル系、ウレタン系の直鎖状または櫛状の高分子共重合物からなる重量平均分子量１０００〜１０００００のもので、直鎖ポリマーの末端、櫛状ポリマーの基体部位、または両者ポリマー中にブロックまたはランダムに塩基性基、酸性基、芳香族基等を含有するものである。このような顔料分散剤は特開昭６０−１６６３１８号公報、特開昭６１−１７４９３９号公報、特開昭４６−７２９４号公報及び特開平９−１６９８２１号公報等に開示されている。
樹脂型顔料分散剤の重量平均分子量が１０００未満では十分な立体障害が得られず、分散効果は低下し、重量平均分子量が１０００００より大きくても逆に凝集作用が生じる場合があり好ましくない。
また、樹脂型顔料分散剤のアミン価は５〜２００mgKOH/g が好ましい。５mgKOH/g 未満では本発明の顔料分散剤との相互作用が十分ではなく、本発明の顔料分散剤が顔料表面に吸着していても十分な分散効果が得られない場合もある。一方、樹脂型顔料分散剤のアミン価が２００mgKOH/g を越えると顔料成分への親和部に比べ、立体障害層が少なくなり、十分な分散効果が得られず好ましくない。
このような樹脂型顔料分散剤は市販のものでよく、例えば、Solsperse 24000 （アビシア製）、Disperbyk-160 、Disperbyk-161 、Disperbyk-162 、Disperbyk-163、Disperbyk-170 （ビックケミー社製）、アジスパーPB711、アジスパーPB821（味の素ファインテクノ株式会社製）等が挙げられる。
一般式（１）で表される顔料分散剤の添加量は、顔料１００重量部に対して０．５〜３０重量部が好ましく、樹脂型顔料分散剤の添加量は顔料１００重量部に対して０．５〜１００重量部が好ましい。
一般式（１）で表される顔料分散剤及び樹脂型顔料分散剤の添加量がそれぞれ０．５重量部より少ないと顔料分散効果が小さく好ましくない。また、一般式（１）で表される顔料分散剤の添加量が３０重量部より多く用いても用いた分の効果が得られなく、樹脂型顔料分散剤の添加量が１００重量部より多く用いると、効果が得られないばかりか、塗膜物性も低下する場合がある。
本発明にかかわる顔料分散剤の使用方法としては、例えば次のような方法がある。
１．顔料と顔料分散剤を予め混合して得られる顔料組成物をビヒクル中に添加して分散する。
２．ビヒクルに顔料と顔料分散剤を別々に添加して分散する。
３．ビヒクルに顔料と顔料分散剤を予め別々に分散し得られた分散体を混合する。この場合、顔料分散剤を溶剤のみで分散しても良い。
４．ビヒクルに顔料を分散した後、得られた顔料分散体に顔料分散剤を添加する。
等の方法があり、これらのいずれによっても目的とする効果が得られる。
顔料組成物の調製法としては、顔料粉末と本発明の顔料分散剤を単に混合しても充分な分散効果が得られるが、ニーダー、ロール、アトライター、スーパーミル、各種粉砕機等により機械的に混合するか、顔料の水または有機溶媒によるサスペンジョン系に本発明の顔料分散剤を含む溶液を添加し、顔料表面に顔料分散剤を沈着させるか、硫酸等の強い溶解力を持つ溶媒に有機顔料と顔料分散剤を共溶解して水等の貧溶媒により共沈させる等の賢密な混合法を行えば、更に良好な結果を得ることができる。
また、非水系または水系ビヒクル、あるいは溶剤中への顔料または顔料分散剤の分散、混合等に、分散機械としてディゾルバー、ハイスピードミキサー、ホモミキサー、ニーダー、ロールミル、サンドミル、アトライター等を使用することにより顔料の良好な分散ができる。
したがって本発明によれば、ライムロジンワニス、ポリアミド樹脂ワニス、ウレタン樹脂ワニスまたは塩化ビニル樹脂ワニス等のグラビアインキ、ニトロセルロースラッカー、アミノアルキッド樹脂の常乾もしくは焼き付け塗料、アクリルラッカー、アミノアクリル樹脂焼き付け塗料、ウレタン系樹脂塗料等の非水系ビヒクルにおいて、顔料を単独で使用した場合に比べ、分散体の粘度の低下および構造粘性の減少等良好な流動性を示すと同時に色分かれ、結晶の変化等の問題もなく印刷物あるいは塗膜の光沢が良くしたがって美麗な製品を得ることができる。
本発明の顔料分散剤及び顔料組成物はまた、水系を含むその他の印刷インキや塗料、さらにはプラスチックの着色においても、分散効果に優れ、着色力にある着色物が得られる。さらには磁性塗料、カラーフィルター、インクジェット等、高度な顔料分散が要求される用途に対しても有効である。
本発明の顔料分散体に使用される樹脂は通常の塗料またはインキに使用されるあらゆるものを使用することができ、例えば、ニトロセルロース、酢酸セルロース、エチルセルロース、ウレタン樹脂、ポリアミド樹脂、ポリビニルブチラール樹脂、アクリル樹脂、ポリエステル樹脂、アルキド樹脂、ライムロジン、トール油ロジン、ウッドロジン、ロジンエステル、ロジン変成フェノール、石油樹脂、アマニ油、桐油、大豆油、マレイン酸樹脂、ビニル樹脂、環化ゴム、塩化ゴム、エチレンー酢酸ビニル樹脂、ギルソナイト、ダンマル、セラック、エポキシ樹脂、塩化ビニル、シリコン樹脂、メラミン樹脂、尿素樹脂、ベンゾグアナミン樹脂等がある。中でも、分子量５０００〜１０００００の通常インキ等のバインダーに用いられるウレタン樹脂については従来の顔料分散剤では効果がほとんど認められない顔料分散が困難な樹脂であるが、本発明の顔料組成物を使用すると特異的に大きな効果を得ることができる。
また本発明の顔料分散体に使用される樹脂は上記の樹脂のうち１種類またはそれ以上を使用しても良く、１種類またはそれ以上の樹脂を用いて分散した高濃度顔料分散体を他の樹脂で希釈して使用しても良い。
一般的に印刷インキ等のバインダーに使用されるウレタン樹脂はポリヒドロキシ化合物とポリイソシアネートとの反応により得られる成分を主骨格とするがバインダーとしての性能を付与する目的でしばしばグリコール類、ジアミン類、アミノアルコール類等の化合物を１種または２種以上用いて鎖延長反応と呼ばれる反応によって高分子量化されることが多いが、本発明の顔料分散体に用いられる樹脂はジアミン類またはアミノアルコール類により鎖延長反応を行うことにより樹脂１分子中に少なくとも１個以上の尿素結合を有する塩基性の比較的強いウレタン樹脂において本発明の顔料組成物およびそれを用いた顔料分散体は顕著な効果を示す。
本発明の顔料分散体に用いられる有機溶剤としてはトルエン等の芳香族炭化水素、ミネラルスピリット等の石油系炭化水素、クロロベンゼン等のハロゲン炭化水素、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノン等のケトン類、酢酸エチル、酢酸ブチル、酢酸アミル、２−エトキシエチルアセタート等のエステル類、メタノール、エタノール、プロパノール、ブタノール等のアルコール類、エチルセロソルブ、ブチルセロソルブ等のセロソルブ類等であるが、特に好ましいのはケトン類、アルコール類、セロソルブ類、エステル類等の極性の高い有機溶剤である。当然のことながら有機溶剤は２種またはそれ以上の混合物であっても差し支えない。
本発明の顔料組成物または顔料分散体は印刷インキまたは塗料に使用することができ、その場合に用いられる印刷インキ用ビヒクルまたは塗料用添加剤としては、消泡剤、レベリング剤、アンチブロッキング剤、界面活性剤、粘度調整剤、ワックス等がある。
Hereinafter, the present invention will be described in detail.
The pigment dispersant of the present invention is obtained by introducing sulfonic acid into a condensed azo pigment and converting the sulfonic acid into a metal salt.
Specific examples of the condensed azo pigments used in the synthesis of the pigment dispersant of the present invention are shown by the generic name of the color index, pigment red 144, 166, 214, 220, 221, 242, 248, 262, pigment. Brown 23, 42 and the like.
In the general formula (1), M represents one equivalent of a divalent or trivalent metal, and examples thereof include calcium, barium, magnesium, iron, aluminum, nickel, cobalt, and strontium.
The number of substituents of sulfonic acid is 1 to 3, and they may be mixed. When the number of substituents of sulfonic acid is 4 or more, not only a sufficient effect cannot be obtained, but also the migration property is deteriorated. Although the number of substituents of sulfonic acid may be represented by the average number of substituents, the average number of substituents is preferably 1 to 2.
The method for producing the pigment dispersant of the present invention is as follows as an example.
First, the condensed azo pigment is dissolved in concentrated sulfuric acid, and sulfonated at room temperature or heated, and then the suspension obtained by injecting the sulfuric acid solution into a sufficient amount of ice water is filtered, washed with water, and sulfonated. Get a press cake.
The metal salt compound represented by the general formula (1) is obtained by reslurrying the press cake obtained by the above operation with water or an organic solvent, and a powder or an aqueous solution of an equimolar strong metal hydrochloride, sulfate, nitrate or the like. After stirring, it can be obtained by filtration, washing with water and drying.
The pigment dispersant obtained in the present invention usually exhibits an effect on various pigments used in printing inks or paints, but particularly exhibits an excellent effect on naphthol pigments and condensed azo pigments. Specific examples of naphthol pigments are represented by generic names of color indexes. Pigment Red 2, 3, 5, 7, 9, 12, 14, 22, 23, 31, 112, 146, 170, 171, 175 176, 185, Pigment Orange 5, 24, 38, Pigment Brown 25, Pigment Violet 32, and the like. As specific examples of the condensed azo pigment, the generic name of the color index indicates pigment red 144, 166, 214, 220, 221, 242, 248, 262, pigment orange 31, pigment brown 23, 41, 42 etc.
In the pigment composition of the present invention, the pigment dispersant represented by the general formula (1) is added to the pigment alone or in combination with a resin-type pigment dispersant.
The resin-type pigment dispersant used in the pigment composition of the present invention has a weight average molecular weight of 1,000 to 100,000 consisting of a polyester-based, acrylic-based, or urethane-based linear or comb-like polymer. It contains a basic group, an acidic group, an aromatic group, or the like in the end of the chain polymer, the base portion of the comb-like polymer, or in both polymers in a block or randomly. Such pigment dispersants are disclosed in JP-A-60-166318, JP-A-61-174939, JP-A-46-7294, JP-A-9-169821 and the like.
If the weight average molecular weight of the resin-type pigment dispersant is less than 1000, sufficient steric hindrance cannot be obtained, the dispersion effect is lowered, and even if the weight average molecular weight is more than 100,000, an aggregating action may occur on the contrary.
The amine value of the resin type pigment dispersant is preferably 5 to 200 mg KOH / g. If it is less than 5 mg KOH / g, the interaction with the pigment dispersant of the present invention is not sufficient, and even if the pigment dispersant of the present invention is adsorbed on the pigment surface, a sufficient dispersion effect may not be obtained. On the other hand, if the amine value of the resin-type pigment dispersant exceeds 200 mg KOH / g, the steric hindrance layer is reduced as compared with the affinity part for the pigment component, and a sufficient dispersion effect cannot be obtained, which is not preferable.
Such resin-type pigment dispersants may be commercially available, for example, Solsperse 24000 (manufactured by Avicia), Disperbyk-160, Disperbyk-161, Disperbyk-162, Disperbyk-163, Disperbyk-170 (manufactured by BYK Chemie), Ajispur PB711, Ajisper PB821 (manufactured by Ajinomoto Fine Techno Co., Ltd.) and the like.
The addition amount of the pigment dispersant represented by the general formula (1) is preferably 0.5 to 30 parts by weight with respect to 100 parts by weight of the pigment, and the addition amount of the resin type pigment dispersant is with respect to 100 parts by weight of the pigment. 0.5-100 weight part is preferable.
When the addition amount of the pigment dispersant represented by the general formula (1) and the resin type pigment dispersant is less than 0.5 parts by weight, the pigment dispersion effect is small, which is not preferable. Further, even if the addition amount of the pigment dispersant represented by the general formula (1) is more than 30 parts by weight, the effect of the used amount cannot be obtained, and the addition amount of the resin type pigment dispersant is more than 100 parts by weight. If used, the effect may not be obtained, and the physical properties of the coating film may be lowered.
Examples of the method for using the pigment dispersant according to the present invention include the following methods.
1. A pigment composition obtained by mixing a pigment and a pigment dispersant in advance is added to the vehicle and dispersed.
2. A pigment and a pigment dispersant are added separately to the vehicle and dispersed.
3. A dispersion obtained by separately dispersing a pigment and a pigment dispersant in advance in a vehicle is mixed. In this case, the pigment dispersant may be dispersed only with a solvent.
4). After dispersing the pigment in the vehicle, a pigment dispersant is added to the resulting pigment dispersion.
Any of these methods can achieve the intended effect.
As a method for preparing the pigment composition, a sufficient dispersion effect can be obtained by simply mixing the pigment powder and the pigment dispersant of the present invention. However, the pigment composition can be mechanically processed by a kneader, a roll, an attritor, a super mill, various grinders, etc. Or a solution containing the pigment dispersant of the present invention is added to a suspension system of pigment water or an organic solvent to deposit the pigment dispersant on the pigment surface, or an organic solvent such as sulfuric acid has a strong dissolving power. Even better results can be obtained by performing a sophisticated mixing method such as co-dissolving the pigment and the pigment dispersant and co-precipitating with a poor solvent such as water.
Also, use a dissolver, high-speed mixer, homomixer, kneader, roll mill, sand mill, attritor, etc. as a dispersion machine to disperse or mix pigments or pigment dispersants in non-aqueous or aqueous vehicles or solvents. Thus, good dispersion of the pigment can be achieved.
Therefore, according to the present invention, gravure inks such as lime rosin varnish, polyamide resin varnish, urethane resin varnish, vinyl chloride resin varnish, nitrocellulose lacquer, amino alkyd resin are normally dried or baked paint, acrylic lacquer, amino acrylic resin baked paint In non-aqueous vehicles such as urethane-based resin paints, compared to the case where pigments are used alone, they exhibit good fluidity such as lower dispersion viscosity and reduced structural viscosity, and at the same time, color separation, crystal change, etc. Without any problem, it is possible to obtain a beautiful product with good gloss of printed matter or coating film.
The pigment dispersant and pigment composition of the present invention are also excellent in dispersion effect and can provide a colored product having excellent coloring power in the case of coloring other printing inks and paints containing water. Furthermore, it is also effective for applications that require high pigment dispersion such as magnetic paints, color filters, and ink jets.
As the resin used in the pigment dispersion of the present invention, any of those used in ordinary paints or inks can be used. For example, nitrocellulose, cellulose acetate, ethyl cellulose, urethane resin, polyamide resin, polyvinyl butyral resin, Acrylic resin, polyester resin, alkyd resin, lime rosin, tall oil rosin, wood rosin, rosin ester, rosin modified phenol, petroleum resin, linseed oil, tung oil, soybean oil, maleic acid resin, vinyl resin, cyclized rubber, chlorinated rubber, ethylene Examples include vinyl acetate resin, gilsonite, dammar, shellac, epoxy resin, vinyl chloride, silicon resin, melamine resin, urea resin, and benzoguanamine resin. Among them, a urethane resin used for a binder such as a normal ink having a molecular weight of 5,000 to 100,000 is a resin which is difficult to disperse with a pigment which is hardly recognized by the conventional pigment dispersant, but when the pigment composition of the present invention is used. A particularly large effect can be obtained.
In addition, the resin used in the pigment dispersion of the present invention may be one or more of the above-mentioned resins, and other high-concentration pigment dispersions dispersed using one or more resins may be used. You may dilute and use with resin.
In general, urethane resins used for binders such as printing inks have a main skeleton as a component obtained by the reaction of a polyhydroxy compound and polyisocyanate, but are often glycols, diamines, for the purpose of imparting performance as a binder. In many cases, one or more compounds such as amino alcohols are used to increase the molecular weight by a reaction called chain extension reaction, but the resin used in the pigment dispersion of the present invention is made of diamines or amino alcohols. By performing a chain extension reaction, the pigment composition of the present invention and a pigment dispersion using the same exhibit a remarkable effect in a basic urethane resin having at least one urea bond in one molecule of the resin. .
Examples of the organic solvent used in the pigment dispersion of the present invention include aromatic hydrocarbons such as toluene, petroleum hydrocarbons such as mineral spirits, halogen hydrocarbons such as chlorobenzene, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone. , Esters such as ethyl acetate, butyl acetate, amyl acetate and 2-ethoxyethyl acetate, alcohols such as methanol, ethanol, propanol and butanol, cellosolves such as ethyl cellosolve and butyl cellosolve, etc. Highly polar organic solvents such as ketones, alcohols, cellosolves and esters. Of course, the organic solvent may be a mixture of two or more.
The pigment composition or pigment dispersion of the present invention can be used in printing inks or paints, and as a printing ink vehicle or paint additive used in that case, antifoaming agents, leveling agents, antiblocking agents, There are surfactants, viscosity modifiers, waxes and the like.
以下、実施例により本発明を説明する。例中、部とは重量部を、％とは重量％をそれぞれ表わす。
（製造例１）
９９％硫酸３００部中にピグメントレッド１６６を１５部仕込み、２５℃で３時間反応させた。その反応液を氷水３０００部中に注入し、撹拌後、濾過、２％塩酸水溶液で洗浄した。得られたプレスケーキを水７００部でスラリーとした後、水酸化ナトリウムでｐＨ９に調整した。次いで、６０℃に加熱し、１０％硫酸アルミニウム水溶液５８部仕込み、６０℃で１時間撹拌した後、濾過、水洗、乾燥し、顔料分散剤（ａ）１８部を得た。スルホン酸基の平均置換基数は１．８個であった。
（製造例２）
９９％硫酸３００部中にピグメントレッド２１４を１５部仕込み、３０℃で３時間反応させた。その反応液を氷水３０００部中に注入し、撹拌後、濾過、２％塩酸水溶液で洗浄した。得られたプレスケーキを水７００部でスラリーとした後、水酸化ナトリウムでｐＨ９に調整した。次いで、６０℃に加熱し、１０％塩化カルシウム水溶液２９部仕込み、６０℃で１時間撹拌した後、濾過、水洗、乾燥し、顔料分散剤（ｂ）１７部を得た。スルホン酸基の平均置換基数は１．５個であった。
（製造例３）
９９％硫酸３００部中にピグメントレッド１４４を１５部仕込み、２０℃で３時間反応させた。その反応液を氷水３０００部中に注入し、撹拌後、濾過、２％塩酸水溶液で洗浄した。得られたプレスケーキを水７００部でスラリーとした後、水酸化ナトリウムでｐＨ９に調整した。次いで、６０℃に加熱し、１０％硫酸第一鉄水溶液３３部仕込み、６０℃で１時間撹拌した後、濾過、水洗、乾燥し、顔料分散剤（ｃ）１８部を得た。スルホン酸基の平均置換基数は１．２個であった。
（製造例４）
９９％硫酸３００部中にピグメントレッド２２１を１５部仕込み、２０℃で３時間反応させた。その反応液を氷水３０００部中に注入し、撹拌後、濾過、２％塩酸水溶液で洗浄した。得られたプレスケーキを水７００部でスラリーとした後、水酸化ナトリウムでｐＨ９に調整した。次いで、６０℃に加熱し、１０％塩化ストロンチウム水溶液２５部仕込み、６０℃で１時間撹拌した後、濾過、水洗、乾燥し、顔料分散剤（ｄ）１７部を得た。スルホン酸基の平均置換基数は１．０個であった。
（製造例５）
１００％硫酸３００部中にピグメントレッド１６６を１５部仕込み、２５℃で３時間反応させた。その反応液を氷水３０００部中に注入し、撹拌後、濾過、２％塩酸水溶液で洗浄した。得られたプレスケーキを水７００部でスラリーとした後、水酸化ナトリウムでｐＨ９に調整した。次いで、６０℃に加熱し、１０％硫酸アルミニウム水溶液１２８部仕込み、６０℃で１時間撹拌した後、濾過、水洗、乾燥し、顔料分散剤（ｅ）２０部を得た。スルホン酸基の平均置換基数は４．０個であった。
（実施例１〜１６、比較例１〜４）
表１に示すように顔料分散剤（ａ）〜（ｄ）の何れかを添加した顔料組成物１０部、グラビアインキ用ワニス（ニトロセルロース樹脂１２％、酢酸エチル３３％、トルエン３０％、イソプロピルアルコール１５％、メタノール１０％）９０部および３ｍｍガラスビーズ１００部と混合しペイントコンディショナーで６０分間分散してグラビアインキを作成した。また、比較例として顔料分散剤を添加せずに各種顔料のみを同様に分散してグラビアインキを作成した。作成したインキの粘度をＢ型粘度計（６ｒｐｍ）で測定した結果および作成したインキをバーコーターでフィルムに展色した際の乾燥皮膜の光沢値（６０゜）を表１に示す。本発明の顔料分散剤を使用したものは、何れの顔料においても低粘度で優れた流動性を示し、さらに塗膜光沢も優れるものであった。
Hereinafter, the present invention will be described by way of examples. In the examples, “part” represents “part by weight” and “%” represents “% by weight”.
(Production Example 1)
15 parts of Pigment Red 166 was charged in 300 parts of 99% sulfuric acid and reacted at 25 ° C. for 3 hours. The reaction solution was poured into 3000 parts of ice water, stirred, filtered, and washed with 2% aqueous hydrochloric acid. The obtained press cake was slurried with 700 parts of water and then adjusted to pH 9 with sodium hydroxide. Subsequently, it heated at 60 degreeC, 58 parts of 10-% aluminum sulfate aqueous solution was prepared, and it stirred at 60 degreeC for 1 hour, Then, it filtered, washed with water, and dried and obtained 18 parts of pigment dispersant (a). The average number of substituents of the sulfonic acid group was 1.8.
(Production Example 2)
15 parts of Pigment Red 214 was charged in 300 parts of 99% sulfuric acid and reacted at 30 ° C. for 3 hours. The reaction solution was poured into 3000 parts of ice water, stirred, filtered, and washed with 2% aqueous hydrochloric acid. The obtained press cake was slurried with 700 parts of water and then adjusted to pH 9 with sodium hydroxide. Subsequently, the mixture was heated to 60 ° C., 29 parts of 10% calcium chloride aqueous solution was charged, and stirred at 60 ° C. for 1 hour, followed by filtration, washing with water and drying to obtain 17 parts of a pigment dispersant (b). The average number of substituents of the sulfonic acid group was 1.5.
(Production Example 3)
15 parts of Pigment Red 144 was charged in 300 parts of 99% sulfuric acid and reacted at 20 ° C. for 3 hours. The reaction solution was poured into 3000 parts of ice water, stirred, filtered, and washed with 2% aqueous hydrochloric acid. The obtained press cake was slurried with 700 parts of water and then adjusted to pH 9 with sodium hydroxide. Next, the mixture was heated to 60 ° C., charged with 33 parts of a 10% ferrous sulfate aqueous solution, stirred at 60 ° C. for 1 hour, filtered, washed with water, and dried to obtain 18 parts of a pigment dispersant (c). The average number of substituents of the sulfonic acid group was 1.2.
(Production Example 4)
15 parts of Pigment Red 221 was charged in 300 parts of 99% sulfuric acid and reacted at 20 ° C. for 3 hours. The reaction solution was poured into 3000 parts of ice water, stirred, filtered, and washed with 2% aqueous hydrochloric acid. The obtained press cake was slurried with 700 parts of water and then adjusted to pH 9 with sodium hydroxide. Next, the mixture was heated to 60 ° C., charged with 25 parts of a 10% aqueous strontium chloride solution, stirred at 60 ° C. for 1 hour, filtered, washed with water, and dried to obtain 17 parts of a pigment dispersant (d). The average number of substituents of the sulfonic acid group was 1.0.
(Production Example 5)
15 parts of Pigment Red 166 was charged in 300 parts of 100% sulfuric acid and reacted at 25 ° C. for 3 hours. The reaction solution was poured into 3000 parts of ice water, stirred, filtered, and washed with 2% aqueous hydrochloric acid. The obtained press cake was slurried with 700 parts of water and then adjusted to pH 9 with sodium hydroxide. Next, the mixture was heated to 60 ° C., charged with 128 parts of a 10% aluminum sulfate aqueous solution, stirred at 60 ° C. for 1 hour, filtered, washed with water and dried to obtain 20 parts of a pigment dispersant (e). The average number of substituents of the sulfonic acid group was 4.0.
(Examples 1-16, Comparative Examples 1-4)
As shown in Table 1, 10 parts of pigment composition to which any of pigment dispersants (a) to (d) is added, varnish for gravure ink (nitrocellulose resin 12%, ethyl acetate 33%, toluene 30%, isopropyl alcohol A gravure ink was prepared by mixing with 90 parts of 15% (10% methanol) and 100 parts of 3 mm glass beads and dispersing with a paint conditioner for 60 minutes. Further, as a comparative example, gravure ink was prepared by similarly dispersing only various pigments without adding a pigment dispersant. Table 1 shows the results of measuring the viscosity of the prepared ink with a B-type viscometer (6 rpm) and the gloss value (60 °) of the dried film when the prepared ink is developed on a film with a bar coater. Those using the pigment dispersant of the present invention exhibited excellent fluidity with low viscosity in any of the pigments, and also had excellent coating gloss.
表２に示すように顔料分散剤（ａ）〜（ｅ）の何れかを添加した顔料組成物２０部、グラビアインキ用ワニス（ウレタン樹脂１５％、酢酸エチル６５％、イソプロピルアルコール２０％）８０部、樹脂型顔料分散剤（味の素ファインテクノ株式会社製「アジスパーPB821」）２部および３ｍｍガラスビーズ１００部と混合しペイントコンディショナーで６０分間分散して顔料分散体を作成した。また、比較例として各種顔料単独を同様に分散して顔料分散体を作成した。尚、上記のウレタン樹脂としては３−メチル−１，５−ペンタンジオールとアジピン酸を縮重合したポリエステルポリオールとイソホロンジイソシアネートを縮重合して得られたプレポリマーをイソホロンジアミンで鎖延長した重量平均分子量約３００００の尿素結合含有ウレタン樹脂を用いた。
作成した顔料分散体の粘度をＢ型粘度計（６ｒｐｍ）で測定した結果および作成した顔料分散体に溶剤（酢酸エチル７０％、イソプロピルアルコール３０％からなる）を加え、ザーンカップＮＯ．４で１４〜１６秒に調整して作成したグラビアインキをバーコーターでフィルムに展色した際の乾燥皮膜の光沢値（６０゜）を表２に示す。本発明の顔料分散剤を使用したものは、何れの顔料においても低粘度で優れた流動性を示し、さらに塗膜光沢も優れるものであった。また、ナイロンフィルムへの展色物の塗布面を未塗布のナイロンフィルムと密着させ、この試験片を１００℃で１時間煮沸した後、未塗布フィルムへの色相の移行性を調べた結果（ブリード試験）、表２に示すようにスルホン酸基の平均置換基数が４．０個、即ち、スルホン酸基が一分子中に４個以上ある化合物を含有する顔料分散剤（ｅ）を使用したものは色相が移行して未塗布フィルムが着色してしまったが、本発明による顔料分散剤を使用したものは着色しなかった。
As shown in Table 2, 20 parts of pigment composition to which any of pigment dispersants (a) to (e) is added, varnish for gravure ink (urethane resin 15%, ethyl acetate 65%, isopropyl alcohol 20%) 80 parts Then, 2 parts of a resin-type pigment dispersant (“Ajisper PB821” manufactured by Ajinomoto Fine Techno Co., Ltd.) and 100 parts of 3 mm glass beads were mixed and dispersed with a paint conditioner for 60 minutes to prepare a pigment dispersion. As a comparative example, a pigment dispersion was prepared by dispersing various pigments in the same manner. In addition, as said urethane resin, the weight average molecular weight which carried out the chain extension of the prepolymer obtained by polycondensing the polyester polyol and isophorone diisocyanate which polycondensated 3-methyl- 1,5-pentanediol and adipic acid with isophorone diamine. About 30000 urea bond-containing urethane resin was used.
The viscosity of the prepared pigment dispersion was measured with a B-type viscometer (6 rpm) and a solvent (consisting of 70% ethyl acetate and 30% isopropyl alcohol) was added to the prepared pigment dispersion. Table 2 shows the gloss value (60 °) of the dried film when the gravure ink prepared by adjusting to 4 to 14 to 16 seconds is developed on a film with a bar coater. Those using the pigment dispersant of the present invention exhibited excellent fluidity with low viscosity in any of the pigments, and also had excellent coating gloss. In addition, the coated surface of the color-extended product on the nylon film was brought into intimate contact with the uncoated nylon film, and the test piece was boiled at 100 ° C. for 1 hour, and then the hue transferability to the uncoated film was examined (bleed). Test), as shown in Table 2, using a pigment dispersant (e) containing a compound having an average number of sulfonic acid groups of 4.0, that is, 4 or more sulfonic acid groups in one molecule The hue shifted and the uncoated film was colored, but those using the pigment dispersant according to the present invention were not colored.
Claims (6)
一般式（１）
General formula (1)
A printing ink comprising the pigment dispersion according to claim 4.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006265528A (en) * | 2005-02-22 | 2006-10-05 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant and its use |
| JP2011057823A (en) * | 2009-09-09 | 2011-03-24 | Kao Corp | Method for producing nonaqueous pigment dispersion |
| JP2011219741A (en) * | 2010-03-25 | 2011-11-04 | Mitsubishi Chemicals Corp | Pigment dispersion, colored resin composition, color filter, liquid crystal display, and organic el display |
| KR101620843B1 (en) | 2014-04-02 | 2016-05-13 | 한국교통대학교산학협력단 | pigment additives, their preparation and compositions containing the same |
| CN116333527A (en) * | 2023-04-24 | 2023-06-27 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998041580A1 (en) * | 1997-03-19 | 1998-09-24 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Condensed azo compound and process for producing the same |
| JPH11228858A (en) * | 1998-02-09 | 1999-08-24 | Sumitomo Chem Co Ltd | Condensed azo pigment derivative and pigment composition containing the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1998041580A1 (en) * | 1997-03-19 | 1998-09-24 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Condensed azo compound and process for producing the same |
| JPH11228858A (en) * | 1998-02-09 | 1999-08-24 | Sumitomo Chem Co Ltd | Condensed azo pigment derivative and pigment composition containing the same |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006265528A (en) * | 2005-02-22 | 2006-10-05 | Dainichiseika Color & Chem Mfg Co Ltd | Pigment dispersant and its use |
| JP4668801B2 (en) * | 2005-02-22 | 2011-04-13 | 大日精化工業株式会社 | Pigment dispersant and use thereof |
| JP2011057823A (en) * | 2009-09-09 | 2011-03-24 | Kao Corp | Method for producing nonaqueous pigment dispersion |
| JP2011219741A (en) * | 2010-03-25 | 2011-11-04 | Mitsubishi Chemicals Corp | Pigment dispersion, colored resin composition, color filter, liquid crystal display, and organic el display |
| KR101620843B1 (en) | 2014-04-02 | 2016-05-13 | 한국교통대학교산학협력단 | pigment additives, their preparation and compositions containing the same |
| CN116333527A (en) * | 2023-04-24 | 2023-06-27 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
| CN116333527B (en) * | 2023-04-24 | 2023-12-01 | 金华贝尔油墨有限公司 | Preparation method of renewable degradable ink |
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