JPH111627A - Colorant composition, its production, dry-and wet-process developing agent for electrophotography and ink colorant for ink jet - Google Patents
Colorant composition, its production, dry-and wet-process developing agent for electrophotography and ink colorant for ink jetInfo
- Publication number
- JPH111627A JPH111627A JP17104997A JP17104997A JPH111627A JP H111627 A JPH111627 A JP H111627A JP 17104997 A JP17104997 A JP 17104997A JP 17104997 A JP17104997 A JP 17104997A JP H111627 A JPH111627 A JP H111627A
- Authority
- JP
- Japan
- Prior art keywords
- colorant
- resin
- composition
- dye
- developer
- 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.)
- Granted
Links
- 239000003086 colorant Substances 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 239000003795 chemical substances by application Substances 0.000 title abstract description 8
- 238000000034 method Methods 0.000 title abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920000098 polyolefin Polymers 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229920002050 silicone resin Polymers 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 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 abstract 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 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 238000013019 agitation Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 239000011369 resultant mixture Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 37
- 239000000049 pigment Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 19
- 239000000976 ink Substances 0.000 description 16
- 238000004040 coloring Methods 0.000 description 12
- -1 Permanent Red 4R Chemical compound 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- CNPVJWYWYZMPDS-UHFFFAOYSA-N 2-methyldecane Chemical compound CCCCCCCCC(C)C CNPVJWYWYZMPDS-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000002612 dispersion medium Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229920006228 ethylene acrylate copolymer Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003302 ferromagnetic material Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000005291 magnetic effect Effects 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- FWLHAQYOFMQTHQ-UHFFFAOYSA-N 2-N-[8-[[8-(4-aminoanilino)-10-phenylphenazin-10-ium-2-yl]amino]-10-phenylphenazin-10-ium-2-yl]-8-N,10-diphenylphenazin-10-ium-2,8-diamine hydroxy-oxido-dioxochromium Chemical compound O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.O[Cr]([O-])(=O)=O.Nc1ccc(Nc2ccc3nc4ccc(Nc5ccc6nc7ccc(Nc8ccc9nc%10ccc(Nc%11ccccc%11)cc%10[n+](-c%10ccccc%10)c9c8)cc7[n+](-c7ccccc7)c6c5)cc4[n+](-c4ccccc4)c3c2)cc1 FWLHAQYOFMQTHQ-UHFFFAOYSA-N 0.000 description 1
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical class CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- DWDURZSYQTXVIN-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-methyliminocyclohexa-2,5-dien-1-ylidene)methyl]aniline Chemical compound C1=CC(=NC)C=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 DWDURZSYQTXVIN-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000692870 Inachis io Species 0.000 description 1
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Chemical class CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene 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
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 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
- YFVOQMWSMQHHKP-UHFFFAOYSA-N cobalt(2+);oxygen(2-);tin(4+) Chemical compound [O-2].[O-2].[O-2].[Co+2].[Sn+4] YFVOQMWSMQHHKP-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Chemical class CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JMXROTHPANUTOJ-UHFFFAOYSA-H naphthol green b Chemical compound [Na+].[Na+].[Na+].[Fe+3].C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21 JMXROTHPANUTOJ-UHFFFAOYSA-H 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 235000019271 petrolatum Nutrition 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
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 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
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Developing Agents For Electrophotography (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、着色剤組成物及び
その製造方法並びにこのものを用いた電子写真用乾式又
は湿式現像剤及びインクジェット用インキ着色剤に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a colorant composition and a method for producing the same, and a dry or wet developer for electrophotography and an ink colorant for ink jet using the same.
【０００２】[0002]
【従来の技術】電子写真法、静電記録法等による静電写
真法で形成される静電潜像の可視化を湿式現像法で行う
場合には、液体現像剤が使用される。液体現像剤は一般
に担体液と呼ばれる高絶縁性で低誘電率の有機溶媒中
に、トナーと呼ばれる着色剤や樹脂を、界面活性剤から
なる分散安定剤であるナフテン酸金属塩とレシチン等の
極性制御剤と共に分散したものである。現像剤の使用中
又は保存中に、現像剤中のトナーは安定に分散している
ことが要求される。2. Description of the Related Art In the case where an electrostatic latent image formed by an electrophotographic method such as an electrophotographic method or an electrostatic recording method is visualized by a wet developing method, a liquid developer is used. A liquid developer consists of a colorant or a resin called a toner in a highly insulating and low dielectric constant organic solvent generally called a carrier liquid, which is a dispersion stabilizer consisting of surfactants such as naphthenic acid metal salt and lecithin. It is dispersed together with a control agent. During use or storage of the developer, the toner in the developer is required to be stably dispersed.
【０００３】このようなトナーを着色するために使用さ
れる着色剤としては、カーボンブラックのような無機顔
料やフタロシアニンブルー、スカイブルー、ローダミン
レーキ、マラカイトグリーンレーキ、メチルバイオレッ
トレーキ、ピーコックブルーレーキ、ナフトールグリー
ンＢ、ナフトールグリーンＹ、ナフトールイエローＳ、
パーマネントレッド４Ｒ、ブリリアントファストスカー
レット、ハンザイエロー、ベンジジンイエロー等の有機
顔料等が知られている。The coloring agents used for coloring such toners include inorganic pigments such as carbon black, phthalocyanine blue, sky blue, rhodamine lake, malachite green lake, methyl violet lake, peacock blue lake, and naphthol. Green B, Naphthol Green Y, Naphthol Yellow S,
Organic pigments such as Permanent Red 4R, Brilliant Fast Scarlet, Hansa Yellow and Benzidine Yellow are known.
【０００４】しかしながら、これら多くの顔料は分散性
がよくないために、またそのもの自体が極性制御性を持
たないために、これらの顔料を用いた液体現像剤では、
長期に亘って使用又は保存すると、分散安定剤や極性制
御剤は担体液に取り込まれるなどして、分散安定剤や極
性制御剤はその機能を失ない、分散安定剤及び極性制御
剤が作用しなくなったトナーは凝集を起こしたり、極性
が不十分となり、画像品質の低下を招くという欠点があ
った。However, since many of these pigments have poor dispersibility and do not themselves have polarity controllability, liquid developers using these pigments have
When used or stored for a long period of time, the dispersion stabilizer and the polarity control agent are taken into the carrier liquid, and the dispersion stabilizer and the polarity control agent do not lose their functions. The missing toner has a drawback that it causes aggregation or insufficient polarity, resulting in deterioration of image quality.
【０００５】そこでこのような欠点を改良するため、顔
料がよくなじむように表面処理を施したり、或いはカー
ボンブラックを用いカーボンブラックをグラフト化して
分散性や極性制御性を与える提案がなされているが、未
だ満足し得る結果は得られていない。しかも、従来の着
色剤は透明性、着色力に劣るため、カラートナー用とし
ても満足し得るものではなかった。In order to improve such disadvantages, it has been proposed to apply a surface treatment so that the pigment can be well blended, or to graft carbon black using carbon black to give dispersibility and polarity controllability. However, satisfactory results have not yet been obtained. In addition, conventional colorants are inferior in transparency and tinting strength, and are not satisfactory for color toners.
【０００６】特公昭５８−９４１８号にはチオインゴイ
ド系顔料を含有する静電写真用液体現像剤が示されてい
る。このチオインジゴイド系顔料をフルカラー用のマゼ
ンタトナーとして用いることもできるが、その場合には
赤味が弱く、分光特性的にマゼンタには好ましくない。
また、特開昭４９−９９０３３号、特開昭４９−１３４
３３３号、特開昭４６−１６３６号等のように、ＳｉＯ
2や樹脂を染料で染着したトナーも提案されている。し
かしながら、これらの液体トナーは着色力が弱く画像濃
度が低いという問題点があった。JP-B-58-9418 discloses a liquid developer for electrostatography containing a thioingoid pigment. The thioindigo pigment can be used as a full-color magenta toner, but in this case, the redness is weak and the spectral characteristics are not preferable for magenta.
Also, JP-A-49-99033, JP-A-49-134
No. 333, JP-A-46-1636, etc.
2 and a toner in which a resin is dyed with a dye have also been proposed. However, these liquid toners have a problem that the coloring power is weak and the image density is low.
【０００７】電子写真法の乾式現像剤に色素を使用する
場合には、該色素を必要に応じ他の添加剤と共に樹脂分
散媒中に分散した後、樹脂を微粉砕したものを用いる。
破砕して得られる樹脂粒子の表面は含有する色素の影響
が避けられない。特に色素として顔料を使用した場合に
は、顔料と樹脂の界面で破砕が起こり、この場合には、
顔料の表面が破砕された粒子表面に露出することも起き
る。また、電子写真複写機の現像剤においては、要求さ
れる複写画像の色相、色調によって現像剤に使用される
色素も限定されることになる。When a dye is used in a dry developer for electrophotography, the dye is dispersed in a resin dispersion medium together with other additives, if necessary, and then the resin is finely pulverized.
The surface of the resin particles obtained by crushing is inevitably affected by the contained dye. In particular, when a pigment is used as a pigment, crushing occurs at the interface between the pigment and the resin, and in this case,
The surface of the pigment may be exposed on the surface of the crushed particles. Further, in the developer of the electrophotographic copying machine, the dye used in the developer is also limited depending on the hue and color tone of the copy image required.
【０００８】従って、電子写真現像剤のキャリアとの摩
擦によって正に帯電する色素が少なく、要求する複写画
像の色相から選定した色素が、キャリアとの摩擦に際し
て正帯電性のものである場合には、その現像剤粒子の表
面の微小部分の帯電性および各粒子間の帯電性の点で、
均一性に欠けてしまうという問題点を有している。Therefore, when the amount of the dye which is positively charged due to friction with the carrier of the electrophotographic developer is small, and the dye selected from the hue of the required copy image is positively charged upon friction with the carrier, , In terms of the chargeability of minute portions on the surface of the developer particles and the chargeability between each particle,
There is a problem of lack of uniformity.
【０００９】[0009]
【発明が解決しようとする課題】本発明の課題は、色素
と樹脂を含有する着色剤組成物において、分散性及び極
性制御性が良好な色素を含有する着色剤組成物及びその
製造方法並びに該着色剤組成物を用いた電子写真用乾式
及び湿式現像剤及びインクジェット用インキ着色剤を提
供することである。SUMMARY OF THE INVENTION An object of the present invention is to provide a colorant composition containing a dye and a resin, which has good dispersibility and good polarity controllability, a method for producing the same, and a method for producing the same. An object of the present invention is to provide a dry and wet developer for electrophotography and a colorant for ink jet ink using a colorant composition.
【００１０】[0010]
【課題を解決するための手段】本発明者らは上記の如き
静電的潜像の現像剤の欠陥に鑑み、上記の条件を満たす
べく、色素の構造について種々研究した結果、特定の構
造式で表わされる色素を現像剤の着色剤として使用する
ことにより、前記した条件においてもすぐれた効果を発
揮しうることを知見し本発明を完成した。本発明によれ
ば、第一に、色素および樹脂を少なくとも含む着色剤組
成物において、色素が一般式（１）で示される色素であ
ることを特徴とする着色剤組成物が提供される。Means for Solving the Problems In view of the above-described defect of the developer of the electrostatic latent image, the present inventors have conducted various studies on the structure of the dye in order to satisfy the above conditions. It has been found that by using the dye represented by the formula (1) as a colorant for a developer, excellent effects can be exhibited even under the above-mentioned conditions, and the present invention has been completed. According to the present invention, first, there is provided a colorant composition comprising at least a dye and a resin, wherein the dye is a dye represented by the general formula (1).
【化１】 （式中、Ｒ1〜Ｒ12は、−ＣＯＯＨ、−ＳＯ3Ｈで表され
る酸又はその金属塩、−ＣnＨ2n+1 （ｎは１〜１８の
整数を表わす。) −ＯＣnＨ2n+1（ｎは１〜１８の整数を表わす。） −ＮＨ2、−ＮＯ2、−ＯＨで表される基又は、−Ｈ、−
Ｃｌ、−Ｂｒ、−Ｉ、−Ｆから選ばれる原子を表す。)Embedded image (Wherein, R 1 to R 12 are, -COOH, acid or metal salt thereof represented by -SO 3 H, -C n H 2n + 1 (n is an integer of 1 to 18.) -OC n H 2n + 1 (n is an integer of 1~18.) -NH 2, -NO 2 , a group represented by -OH or, -H, -
Represents an atom selected from Cl, -Br, -I, and -F. )
【００１１】また本発明によれば、第二に上記樹脂がシ
リコーン樹脂、ポリオレフィン、ポリオレフィン共重合
体及びロジン変性樹脂の中から選ばれるものであること
を特徴とする着色剤組成物が提供される。第三に、上記
色素の含有量が１０〜７０ｗｔ％であり、残部が樹脂で
あることを特徴とする着色剤組成物が提供される。第四
に、上記色素を水に溶かした後に、樹脂溶液を加え、撹
拌混合し水を分離し、残った色素を含む樹脂溶液を乾燥
させ粉砕することを特徴とする着色剤組成物の製造方法
が提供される。第五に、上記着色剤組成物からなる電子
写真用乾式現像剤が提供される。第六に、上記着色剤組
成物からなる電子写真用湿式現像剤が提供される。第七
に、上記着色剤組成物からなるインクジェット用インキ
着色剤が提供される。According to the present invention, secondly, there is provided a colorant composition characterized in that the resin is selected from a silicone resin, a polyolefin, a polyolefin copolymer and a rosin-modified resin. . Third, there is provided a colorant composition characterized in that the content of the dye is 10 to 70 wt% and the balance is resin. Fourthly, a method for producing a colorant composition, comprising dissolving the dye in water, adding a resin solution, stirring and mixing to separate water, drying and pulverizing the resin solution containing the remaining dye. Is provided. Fifth, there is provided a dry developer for electrophotography comprising the above colorant composition. Sixth, there is provided an electrophotographic wet developer comprising the above colorant composition. Seventh, there is provided an ink jet ink colorant comprising the above colorant composition.
【００１２】[0012]
【発明の実施の形態】本発明では、下記一般式（１）で
示される色素が用いられる。DESCRIPTION OF THE PREFERRED EMBODIMENTS In the present invention, a dye represented by the following general formula (1) is used.
【化１】 （式中、Ｒ1〜Ｒ12は、−ＣＯＯＨ、−ＳＯ3Ｈで表され
る酸又はその金属塩、−ＣnＨ2n+1 （ｎは１〜１８の
整数を表わす。) −ＯＣnＨ2n+1（ｎは１〜１８の整数を表わす。） −ＮＨ2、−ＮＯ2、−ＯＨで表される基又は、−Ｈ、−
Ｃｌ、−Ｂｒ、−Ｉ、−Ｆから選ばれる原子を表す。)
本発明で用いられる前記一般式（１）で表わされる色素
の代表的な化合物を示すと、表１の通りである。Embedded image (Wherein, R 1 to R 12 are, -COOH, acid or metal salt thereof represented by -SO 3 H, -C n H 2n + 1 (n is an integer of 1 to 18.) -OC n H 2n + 1 (n is an integer of 1~18.) -NH 2, -NO 2 , a group represented by -OH or, -H, -
Represents an atom selected from Cl, -Br, -I, and -F. )
Table 1 shows typical compounds of the dye represented by the general formula (1) used in the present invention.
【００１３】[0013]
【表１】 [Table 1]
【００１４】本発明の着色剤組成物を得るには、色素
（顔料）を水に溶かした含水液に、更に樹脂分散媒を加
え、フラッシャーと呼ばれるニーダー中でよく混合す
る。この操作により顔料の囲りに存在する水は、後から
添加される樹脂分散媒によって置換される。この操作に
より取出される水を排出し、樹脂溶液中に顔料が分散さ
れた状態とし乾燥させて、溶剤を除去すると、残された
塊りを得る。次にこの塊りを粉砕することにより着色剤
の粉末が得られる。この着色剤は顔料が樹脂によって被
覆されており、印刷インキ、塗料、静電写真用トナーな
どに用いることができる。In order to obtain the colorant composition of the present invention, a resin dispersion medium is further added to a water-containing liquid in which a dye (pigment) is dissolved in water, and the mixture is thoroughly mixed in a kneader called a flasher. By this operation, water existing around the pigment is replaced by a resin dispersion medium added later. The water taken out by this operation is discharged, the pigment is dispersed in the resin solution and dried, and the solvent is removed to obtain the remaining lump. Then, the mass is pulverized to obtain a colorant powder. The coloring agent is obtained by coating a pigment with a resin, and can be used for printing inks, paints, toners for electrophotography, and the like.
【００１５】一般式（１）の色素を含む水溶液に樹脂に
分散させる場合には、樹脂分散媒としては、従来使用さ
れてきた樹脂分散媒であればすべて使用できる。例え
ば、ポリスチレン、スチレン−アクリル酸エステル共重
合体、スチレン−メタクリル酸エステル共重合体、スチ
レン−マレイン酸エステル共重合体、アクリル酸エステ
ル又はメタクリル酸エステル重合体および共重合体、ス
チレン−ジエン系共重合体、ポリエチレン、ポリプロピ
レン、エチレン−酢酸ビニル共重合体、エチレン−アク
リル酸エステル共重合体等の付加重合系樹脂、ポリエス
テル系樹脂、エポキシ系樹脂、フェノール系樹脂等の縮
合系樹脂、ロジンエステル、マレイン化ロジンエステル
等の変性樹脂、シリコーン樹脂、石油樹脂、高級脂肪酸
ワックス、高級アルコール、高級脂肪酸、パラフィンワ
ックス、カルナバワックス、シェラック等の低分子固体
等が単独あるいは組合わせて使用できる。これらの中で
は、ポリエチレン、ポリプロピレン、エチレン−アクリ
ル酸エステル共重合体、エチレン／無水マレイン酸共重
合体のようなポリオレフィン、ポリオレフィン共重合
体、シリコーン樹脂、ロジン変性樹脂が分散性が良好で
あり、良好な結果が得られる。When the resin is dispersed in an aqueous solution containing the dye of the general formula (1), any conventionally used resin dispersion medium can be used as the resin dispersion medium. For example, polystyrene, styrene-acrylate copolymer, styrene-methacrylate copolymer, styrene-maleate copolymer, acrylate or methacrylate polymer and copolymer, styrene-diene copolymer Polymers, polyethylene, polypropylene, ethylene-vinyl acetate copolymers, addition polymerization resins such as ethylene-acrylate copolymers, polyester resins, epoxy resins, condensation resins such as phenolic resins, rosin esters, Modified resins such as maleated rosin esters, silicone resins, petroleum resins, higher fatty acid waxes, higher alcohols, higher fatty acids, paraffin wax, carnauba wax, and low molecular solids such as shellac can be used alone or in combination. Among these, polyethylene, polypropylene, ethylene-acrylate copolymer, polyolefin such as ethylene / maleic anhydride copolymer, polyolefin copolymer, silicone resin, and rosin-modified resin have good dispersibility, Good results are obtained.
【００１６】着色剤組成物製造例を示すと次の通りであ
る（以下、製造例Ａという）。水５０重量部、及び表１
の「色素化合物２」２０重量部をフラッシャーにとり、
よく混合分散した。次に、エチレン−酢ビ共重合体（エ
バフレック２１０ 三井デュポン株式会社製）８０重量
部及びトルエン５０重量部を加え、１００℃で２時間分
散した。分散後、減圧し、水分とトルエンを除去し、粉
砕しフラッシング着色剤を得た。A production example of the colorant composition is as follows (hereinafter referred to as Production Example A). 50 parts by weight of water and Table 1
Take 20 parts by weight of "Dye Compound 2" into a flasher,
Well mixed and dispersed. Next, 80 parts by weight of an ethylene-vinyl acetate copolymer (Evaflec 210 manufactured by Du Pont-Mitsui Co., Ltd.) and 50 parts by weight of toluene were added, and dispersed at 100 ° C. for 2 hours. After dispersion, the pressure was reduced, water and toluene were removed, and the mixture was pulverized to obtain a flushing colorant.
【００１７】前記一般式（１）で表わされる色素を含む
樹脂溶液及びさらにその他の添加剤を含む着色組成物中
の色素の含有量は、使用する目的によって異なる。印刷
インキ及び塗料などの色素を高濃度に含有する固体状、
ペースト状あるいは液状の組成物においては、色素濃度
は約１０重量％〜７０重量％、好ましくは３０重量％〜
６０重量％であり、電子写真用乾式現像剤の着色剤組成
物では、色素の濃度は約２重量％〜１５重量％、好まし
くは３重量％〜１０重量％である。The content of the coloring matter in the resin solution containing the coloring matter represented by the general formula (1) and the coloring composition further containing other additives varies depending on the purpose of use. Solids containing high concentrations of dyes such as printing inks and paints,
In the paste or liquid composition, the pigment concentration is about 10% to 70% by weight, preferably 30% to 70% by weight.
60% by weight, and in the colorant composition of the electrophotographic dry developer, the concentration of the dye is about 2% to 15% by weight, preferably 3% to 10% by weight.
【００１８】電子写真用乾式現像剤を製造する場合に
は、色素を高濃度含有する状態とし、十分混合して分散
させ、そして、色調等を調整し、次に色素の濃度が低い
組成物を製造する。色素が高濃度の組成物は粗粒、粗
粉、微粉、シート状、小塊状等の固体状、あるいはペー
スト状または液状等のいずれの性状にでも差し支えな
い。また、色素の濃度は、最終的な画像記録用現像剤と
して使用する組成物の用途又は状態により定まるもので
あり、いわゆる乾式現像剤、湿式現像剤、静電現像剤等
であり、乾式現像剤は二成分系現像剤および一成分系現
像剤に区分される。In the case of producing a dry developer for electrophotography, a high-concentration dye is contained, thoroughly mixed and dispersed, the color tone is adjusted, and then a composition having a low concentration of the dye is prepared. To manufacture. The composition having a high concentration of the pigment may be in any form such as a solid such as a coarse particle, a coarse powder, a fine powder, a sheet or a small lump, or a paste or a liquid. The concentration of the dye is determined by the use or condition of the composition used as the final image recording developer, and is a so-called dry developer, wet developer, electrostatic developer, or the like. Is classified into a two-component developer and a one-component developer.
【００１９】一成分系乾式現像剤には、主として強磁性
材料を併用する。これらの強磁性材料も本発明の着色組
成物中に必要に応じて添加するものであって、従来公知
の磁性現像剤用として使用されている強磁性微粒状物が
いずれも使用できる。例えば、四三酸化鉄粉、三二酸化
鉄粉等の酸化物、鉄、ニッケル、コバルト等の金属粉等
であり、形状としては立方体状、針状等、形状にこだわ
るものではない。また圧力定着型現像剤では、必要に応
じて添加する可塑化材料としては、使用するものであっ
て、可塑剤、油脂、低融点ワックス、石油樹脂、液状オ
リゴマー樹脂等が挙げられる。The one-component dry developer mainly uses a ferromagnetic material. These ferromagnetic materials are also added as needed to the coloring composition of the present invention, and any of ferromagnetic fine particles conventionally used for magnetic developers can be used. For example, oxides such as triiron tetroxide powder and iron sesquioxide powder, and metal powders such as iron, nickel, and cobalt are not limited to a cubic shape, a needle shape, or the like. In the pressure fixing type developer, as a plasticizing material to be added as necessary, a plasticizer, a fat or oil, a low melting point wax, a petroleum resin, a liquid oligomer resin or the like is used.
【００２０】電子写真用湿式液体現像剤を調製するに
は、着色剤と樹脂を含有する着色剤組成物を担体液中に
分散させることにより製造される。担体液としては、高
絶縁性（電気抵抗１０10Ωｃｍ以上）、低誘電率（誘電
率３以下）の石油系樹脂族炭化水素、ｎ−ヘキサン、リ
グロイン、ｎ−ヘプタン、ｎ−ペプタン、イソドデカ
ン、イソオクタンなどの他の、それらのハロゲン誘導
体、例えば、四塩化炭素、パークロルエチレンなどが挙
げられる。なお、前記の石油系脂肪族炭化水素の市販品
にはエキソン社製の、アンソパーＥ、アイソパーＧ、ア
イソパーＬ、アイソパーＨ、アイソパーＫ、ナフサＮ
ｏ．６、ソルベッソ１００等がある。これらは単独で又
は組合わせて使用される。色素を高濃度に含有するペー
ストまたは液状組成物で使用される溶剤としては、脂肪
族炭化水素系、脂環族炭化水素系、芳香族炭化水素系、
ハロゲン化炭化水素系、エステル系、ケトン系、グリコ
ールエーテル系、アルコール系、水系等が使用され、特
にこれらの中の特定の物質に限定されるものではない。
また、湿式の電子写真現像剤の媒体として使用する場合
には、従来公知の高絶縁性の石油系溶剤、例えば、アイ
ソパーＨ、アイソパーＧ（エッソスタンダード株式会
社）シェルゾール７１（シェル石油株式会社）およびケ
ロシン等を使用する。A wet liquid developer for electrophotography is prepared by dispersing a colorant composition containing a colorant and a resin in a carrier liquid. Examples of the carrier liquid include petroleum resin hydrocarbons having a high insulating property (electric resistance of 10 10 Ωcm or more) and a low dielectric constant (dielectric constant of 3 or less), n-hexane, ligroin, n-heptane, n-heptane, isododecane, Other halogen derivatives thereof such as isooctane, for example, carbon tetrachloride, perchlorethylene and the like. The commercially available petroleum aliphatic hydrocarbons include Ansoper E, Isopar G, Isopar L, Isopar H, Isopar K, and Naphtha N manufactured by Exon.
o. 6, Solvesso 100 and the like. These may be used alone or in combination. As a solvent used in a paste or a liquid composition containing a pigment in a high concentration, aliphatic hydrocarbon-based, alicyclic hydrocarbon-based, aromatic hydrocarbon-based,
Halogenated hydrocarbon-based, ester-based, ketone-based, glycol ether-based, alcohol-based, water-based, and the like are used, and are not particularly limited to specific substances among these.
When used as a medium for a wet electrophotographic developer, conventionally known highly insulating petroleum solvents such as Isopar H and Isopar G (Esso Standard Co., Ltd.) Shell Sol 71 (Shell Petroleum Co., Ltd.) And kerosene.
【００２１】また、色素を更に必要とする場合には、従
来公知の顔料または染料から適切に選択して、本発明で
使用する色素と共に使用する。例えば、有機顔料または
染料としては、フタロシアニン系、アゾ系、アンスラキ
ノン系、ペリノン・ペリレン系、インジゴ・チオインジ
ゴ系、ジオキサジン系、キナクリドン系、イソインドリ
ン系、アニリンブラック系、カーボンブラック系顔料が
挙げられ、無機顔料としては、酸化チタン系、酸化鉄
系、焼成顔料系、紺青、金属粉顔料、体質顔料等が挙げ
られる。電子写真用現像剤として使用する場合において
は、他に従来公知の電荷制御剤、クリーニング剤、現像
剤の流動性の向上剤等を添加することができる。When a dye is further required, it is appropriately selected from conventionally known pigments or dyes and used together with the dye used in the present invention. For example, examples of the organic pigment or dye include phthalocyanine-based, azo-based, anthraquinone-based, perinone-perylene-based, indigo-thioindigo-based, dioxazine-based, quinacridone-based, isoindoline-based, aniline black-based, and carbon black-based pigments. Examples of the inorganic pigment include titanium oxide, iron oxide, calcined pigment, navy blue, metal powder pigment, extender pigment and the like. When used as an electrophotographic developer, a conventionally known charge control agent, cleaning agent, agent for improving the fluidity of the developer, and the like can be added.
【００２２】本発明の着色剤組成物は、その色素成分と
して前記一般式（１）で表わされる色素を選択したの
で、最終的に画像記録用着色組成物として使用するに際
して、粒子間の帯電性のバラつきを少なくすることがで
きる。湿式現像剤として使用するに際しても、界面電位
が一定し、長時間安定して現像することができる。In the colorant composition of the present invention, the dye represented by the general formula (1) is selected as the dye component. Can be reduced. Even when used as a wet developer, the interface potential is constant and development can be performed stably for a long time.
【００２３】[0023]
【実施例】次に、実施例をあげて、本発明を具体的に説
明する。なお文中、部または％とあるのは特に断りのな
い限り重量基準である。Next, the present invention will be specifically described with reference to examples. In the following description, “parts” or “%” is based on weight unless otherwise specified.
【００２４】実施例１ 表１の「色素化合物Ｎｏ．１」３０部をビニルトルエン
／メタクリル酸共重合体７０部とともに、１２０℃の三
本ロールにて十分混練し、色素を分散させた。冷却後粗
砕して色素を３０％の濃度で含有する本発明の高濃度着
色剤組成物の粗粉を得た。次に、この操作でで得た色素
を含む高濃度着色組成物２０部を、上記で使用したビニ
ルトルエン／メタクリル酸共重合体８０部と常法に従っ
て混練し、冷却後粉砕し、更にジェットミルで微粉砕
し、分級して５〜１５μｍの本発明の着色組成物の微粉
末を得た。この着色組成物の摩擦帯電量を測定したとこ
ろ、−９．６μＣ／ｇｒであった。上記の赤色樹脂微粉
末に流動化剤としてコロイダルシリカを添加し、常法に
従い十分混合し、電子写真乾式現像剤とし、キャリアの
磁性鉄分と混合し、負電荷現像剤用電子写真複写機（リ
コピーＦＴ−４０６０）にて複写したところ、画像濃度
１．３６、解像度６．２本／ｍ、階調性８段の鮮明で安
定した複写画像が得られた。Example 1 30 parts of "Dye Compound No. 1" in Table 1 were thoroughly kneaded with 70 parts of a vinyltoluene / methacrylic acid copolymer using a three-roll mill at 120 ° C. to disperse the dye. After cooling, the mixture was crushed to obtain a coarse powder of the high-concentration colorant composition of the present invention containing a dye at a concentration of 30%. Next, 20 parts of the high-concentration coloring composition containing the dye obtained by this operation was kneaded with 80 parts of the vinyltoluene / methacrylic acid copolymer used in the conventional manner, cooled, pulverized, and further jet milled. , And classified to obtain a fine powder of the colored composition of the present invention having a size of 5 to 15 μm. The measured triboelectric charge of the colored composition was -9.6 [mu] C / gr. Add the colloidal silica as a fluidizing agent to the above fine red resin powder and mix well according to the usual method to form an electrophotographic dry developer, mix with the magnetic iron component of the carrier, and use the electrophotographic copying machine for negative charge developer (Recopy FT-4060), a clear and stable copied image having an image density of 1.36, a resolution of 6.2 lines / m, and a gradation of 8 steps was obtained.
【００２５】実施例２ 実施例１の前記構造式で表わされる色素を３０％濃度で
含む高濃度着色組成物２０．８部を、脂肪族炭化水素系
溶媒に可溶のアクリル酸エステル樹脂１５部と共にアイ
ソパーＧ１００部に加え、更にガラスビーズを加えてペ
イントシェイカーにて２０時間分散せしめて、濃厚着色
液を調製した。この濃厚着色液５部をアイソパーＧ１リ
ットル中に加え分散させて、本発明の目的とする電子写
真湿式現像剤を得た。これを湿式電子写真複写機にて複
写したところ、画像濃度１．２５、解像度９．２本／ｍ
で、ＯＨＰの色再現性が良好で、鮮明で落着いた色調の
複写画像が安定して得られた。Example 2 20.8 parts of a high-concentration coloring composition containing the dye represented by the above structural formula of Example 1 at a concentration of 30% was added to 15 parts of an acrylate resin soluble in an aliphatic hydrocarbon solvent. Along with 100 parts of Isopar G, glass beads were further added and dispersed in a paint shaker for 20 hours to prepare a thick colored liquid. 5 parts of this thick colored liquid was added and dispersed in 1 liter of Isopar G to obtain an electrophotographic wet developer intended for the present invention. When this was copied by a wet electrophotographic copying machine, the image density was 1.25 and the resolution was 9.2 lines / m.
As a result, the color reproducibility of the OHP was good, and a clear and calm color copy image was stably obtained.
【００２６】実施例３ 実施例１の着色剤組成物２０部の代りに本発明の色素と
して製造例Ａの着色剤組成物を用いた。同様に乾式トナ
ーを作成し評価したところ、摩擦帯電量が−１４．０μ
Ｃ／ｇｒであった。また、画像濃度は１．３１で、均一
な負極性を示し、実施例１よりは更に鮮明な画像が得ら
れた。解像度は７．２本／ｍｍであった。Example 3 Instead of 20 parts of the colorant composition of Example 1, the colorant composition of Production Example A was used as the coloring matter of the present invention. Similarly, when a dry toner was prepared and evaluated, the triboelectric charge amount was -14.0 μm.
C / gr. Further, the image density was 1.31, showing a uniform negative polarity, and a clearer image was obtained than in Example 1. The resolution was 7.2 lines / mm.
【００２７】実施例４ 実施例２の着色剤組成物３０部に代わりに、本発明の色
素として製造例Ａの着色剤組成物を用いた。同様に湿式
トナーを作成し評価したところ、画色濃度は１．３１で
マゼンタ色の濃い画像を得ることができた。解像度は
９．６本／ｍｍであった。Example 4 Instead of 30 parts of the colorant composition of Example 2, the colorant composition of Production Example A was used as the coloring matter of the present invention. Similarly, when a wet toner was prepared and evaluated, the image color density was 1.31, and a deep magenta image could be obtained. The resolution was 9.6 lines / mm.
【００２８】実施例５ 実施例２、４で得られた液体トナーを、インクジェット
インキとして使用した。このインキは従来のインクジェ
ットインキ（株式会社セイコーエプソンのマッハジェッ
ト用インキ）に比較し、画像濃度が高く、にじみのない
印刷画像を与えるものであった。また、この液体トナー
からなる、塗料及び印刷インキは分散安定性、着色力が
高く、耐光褪色性に優れたものであった。Example 5 The liquid toners obtained in Examples 2 and 4 were used as ink jet inks. This ink has a higher image density and gives a printed image without bleeding as compared with a conventional inkjet ink (ink for Mach Jet manufactured by Seiko Epson Corporation). Further, the paint and printing ink comprising this liquid toner had high dispersion stability and coloring power, and were excellent in light fading resistance.
【００２９】[0029]
【発明の効果】本発明に係る着色剤組成物は分散性及び
極性制御性が良好であり、このものから得られる乾式電
子写真用現像剤によれば、鮮明なコピーが得られる。又
湿式電子写真用現像剤によれば、コピー画像濃度が高
く、色再現性が高い。本発明の着色剤を用いたインクジ
ェット用インキ及び印刷インキ、塗料は分散安定性、着
色力も高い。The colorant composition according to the present invention has good dispersibility and polarity controllability, and a dry electrophotographic developer obtained therefrom can provide a clear copy. Further, according to the developer for wet electrophotography, the copy image density is high and the color reproducibility is high. The inkjet ink, printing ink, and paint using the colorant of the present invention have high dispersion stability and coloring power.
Claims (7)
において、色素が一般式（１）で示される色素であるこ
とを特徴とする着色剤組成物。 【化１】 （式中、Ｒ1〜Ｒ12は、−ＣＯＯＨ、−ＳＯ3Ｈで表され
る酸又はその金属塩、 −ＣnＨ2n+1 （ｎは１〜１８の整数を表わす。) −ＯＣnＨ2n+1（ｎは１〜１８の整数を表わす。） −ＮＨ2、−ＮＯ2、−ＯＨで表される基又は、−Ｈ、 −Ｃｌ、−Ｂｒ、−Ｉ、−Ｆから選ばれる原子を表
す。)1. A colorant composition comprising a colorant and a resin, wherein the colorant is a colorant represented by the general formula (1). Embedded image (Wherein, R 1 to R 12 are, -COOH, acid or metal salt thereof represented by -SO 3 H, -C n H 2n + 1 (n is an integer of 1 to 18.) -OC n H 2n + 1 (n is an integer of 1~18.) -NH 2, -NO 2 , a group represented by -OH or is selected -H, -Cl, -Br, -I, from -F Represents an atom.)
オレフィン、ポリオレフィン共重合体及びロジン変性樹
脂の中から選ばれる少なくとも１種であることを特徴と
する着色剤組成物。2. The colorant composition according to claim 1, wherein the resin according to claim 1 is at least one selected from silicone resins, polyolefins, polyolefin copolymers, and rosin-modified resins.
ｔ％であり、残部が樹脂であることを特徴とする着色剤
組成物。3. The content of the dye of claim 1 is 10 to 70 w.
A colorant composition, wherein the content is t% and the balance is resin.
に、樹脂溶液を加え、撹拌混合し水を分離し、残った色
素を含む樹脂溶液を乾燥させ粉砕することを特徴とする
着色剤組成物の製造方法。4. A coloring agent comprising dissolving the dye according to claim 1 in water, adding a resin solution, stirring and mixing to separate water, and drying and pulverizing the resin solution containing the remaining dye. A method for producing the composition.
子写真用乾式現像剤。5. A dry developer for electrophotography comprising the colorant composition according to claim 1.
子写真用湿式現像剤。6. An electrophotographic wet developer comprising the colorant composition according to claim 1.
ンクジェット用インキ着色剤。7. An ink-jet colorant comprising the colorant composition according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17104997A JP3905599B2 (en) | 1997-06-12 | 1997-06-12 | Colorant composition, production method thereof, dry and wet developer for electrophotography, and ink colorant for ink jet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17104997A JP3905599B2 (en) | 1997-06-12 | 1997-06-12 | Colorant composition, production method thereof, dry and wet developer for electrophotography, and ink colorant for ink jet |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH111627A true JPH111627A (en) | 1999-01-06 |
| JP3905599B2 JP3905599B2 (en) | 2007-04-18 |
Family
ID=15916143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17104997A Expired - Fee Related JP3905599B2 (en) | 1997-06-12 | 1997-06-12 | Colorant composition, production method thereof, dry and wet developer for electrophotography, and ink colorant for ink jet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3905599B2 (en) |
-
1997
- 1997-06-12 JP JP17104997A patent/JP3905599B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP3905599B2 (en) | 2007-04-18 |
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