JPS63248864A - Readily dispersible copper phthalocyanine pigment composition and production thereof - Google Patents
Readily dispersible copper phthalocyanine pigment composition and production thereofInfo
- Publication number
- JPS63248864A JPS63248864A JP8117587A JP8117587A JPS63248864A JP S63248864 A JPS63248864 A JP S63248864A JP 8117587 A JP8117587 A JP 8117587A JP 8117587 A JP8117587 A JP 8117587A JP S63248864 A JPS63248864 A JP S63248864A
- Authority
- JP
- Japan
- Prior art keywords
- copper phthalocyanine
- pigment composition
- ester
- phthalocyanine pigment
- acid ester
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 239000000049 pigment Substances 0.000 title claims abstract description 64
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- -1 sulfuric acid ester Chemical class 0.000 claims abstract description 36
- 238000000227 grinding Methods 0.000 claims abstract description 27
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003014 phosphoric acid esters Chemical class 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 12
- 239000010949 copper Substances 0.000 abstract description 11
- 229910019142 PO4 Inorganic materials 0.000 abstract description 7
- 239000010452 phosphate Substances 0.000 abstract description 7
- 239000011780 sodium chloride Substances 0.000 abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002776 aggregation Effects 0.000 abstract description 5
- 229910052802 copper Inorganic materials 0.000 abstract description 5
- 239000013078 crystal Substances 0.000 abstract description 5
- 239000003960 organic solvent Substances 0.000 abstract description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004220 aggregation Methods 0.000 abstract description 3
- 239000002245 particle Substances 0.000 abstract description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000004202 carbamide Substances 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 238000000034 method Methods 0.000 description 20
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000976 ink Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- QPKQDFUESJXXAW-UHFFFAOYSA-N NC[Cu] Chemical compound NC[Cu] QPKQDFUESJXXAW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000009837 dry grinding Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 150000008379 phenol ethers Chemical class 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000001238 wet grinding Methods 0.000 description 2
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- DFSMJKLTTCAJDF-UHFFFAOYSA-N 1-n,1-n-diethylbutane-1,2-diamine Chemical compound CCC(N)CN(CC)CC DFSMJKLTTCAJDF-UHFFFAOYSA-N 0.000 description 1
- BPZCAJPXNAAAEU-UHFFFAOYSA-N 1-n,1-n-diethylhexane-1,2-diamine Chemical compound CCCCC(N)CN(CC)CC BPZCAJPXNAAAEU-UHFFFAOYSA-N 0.000 description 1
- AKRUIVSMWDCKNI-UHFFFAOYSA-N 1-n,1-n-dimethylbutane-1,2-diamine Chemical compound CCC(N)CN(C)C AKRUIVSMWDCKNI-UHFFFAOYSA-N 0.000 description 1
- RCKMCQKWWTZZKC-UHFFFAOYSA-N 1-n,1-n-dimethylhexane-1,2-diamine Chemical compound CCCCC(N)CN(C)C RCKMCQKWWTZZKC-UHFFFAOYSA-N 0.000 description 1
- QMKFYXRJOZYBIO-UHFFFAOYSA-N 1-n,1-n-dipropylhexane-1,2-diamine Chemical compound CCCCC(N)CN(CCC)CCC QMKFYXRJOZYBIO-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- VCZSCOKOZRRWGQ-UHFFFAOYSA-N 2-methyl-n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CC(C)CN VCZSCOKOZRRWGQ-UHFFFAOYSA-N 0.000 description 1
- PFKIHACEAGQXLE-UHFFFAOYSA-N 2-n',2-n'-dibutylbutane-2,2-diamine Chemical compound CCCCN(C(C)(N)CC)CCCC PFKIHACEAGQXLE-UHFFFAOYSA-N 0.000 description 1
- DQYSALLXMHVJAV-UHFFFAOYSA-M 3-heptyl-2-[(3-heptyl-4-methyl-1,3-thiazol-3-ium-2-yl)methylidene]-4-methyl-1,3-thiazole;iodide Chemical compound [I-].CCCCCCCN1C(C)=CS\C1=C\C1=[N+](CCCCCCC)C(C)=CS1 DQYSALLXMHVJAV-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- VPEHLBKNKJTMAR-UHFFFAOYSA-N [Cu].S(=O)(=O)(N)N Chemical compound [Cu].S(=O)(=O)(N)N VPEHLBKNKJTMAR-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DAMJSIMZZSEQRD-UHFFFAOYSA-N n',n',2-trimethylpropane-1,3-diamine Chemical compound NCC(C)CN(C)C DAMJSIMZZSEQRD-UHFFFAOYSA-N 0.000 description 1
- YXMCJVDGIAFFTR-UHFFFAOYSA-N n',n'-dibutyl-2-methylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CC(C)CN YXMCJVDGIAFFTR-UHFFFAOYSA-N 0.000 description 1
- LDIPAUVCWRHLAM-UHFFFAOYSA-N n',n'-dibutylbutane-1,4-diamine Chemical compound CCCCN(CCCC)CCCCN LDIPAUVCWRHLAM-UHFFFAOYSA-N 0.000 description 1
- PWNDYKKNXVKQJO-UHFFFAOYSA-N n',n'-dibutylethane-1,2-diamine Chemical compound CCCCN(CCN)CCCC PWNDYKKNXVKQJO-UHFFFAOYSA-N 0.000 description 1
- WDCCROLLJZMYQF-UHFFFAOYSA-N n',n'-diethyl-2-methylpropane-1,3-diamine Chemical compound CCN(CC)CC(C)CN WDCCROLLJZMYQF-UHFFFAOYSA-N 0.000 description 1
- JILXUIANNUALRZ-UHFFFAOYSA-N n',n'-diethylbutane-1,4-diamine Chemical compound CCN(CC)CCCCN JILXUIANNUALRZ-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- TZBFEBDATQDIHX-UHFFFAOYSA-N n',n'-diethylhexane-1,6-diamine Chemical compound CCN(CC)CCCCCCN TZBFEBDATQDIHX-UHFFFAOYSA-N 0.000 description 1
- GCOWZPRIMFGIDQ-UHFFFAOYSA-N n',n'-dimethylbutane-1,4-diamine Chemical compound CN(C)CCCCN GCOWZPRIMFGIDQ-UHFFFAOYSA-N 0.000 description 1
- DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
- XKXKBRKXBRLPNS-UHFFFAOYSA-N n'-(2-ethylhexyl)propane-1,3-diamine Chemical compound CCCCC(CC)CNCCCN XKXKBRKXBRLPNS-UHFFFAOYSA-N 0.000 description 1
- FNZNHTIBNDAHFH-UHFFFAOYSA-N n'-cyclohexyl-n'-methylethane-1,2-diamine Chemical compound NCCN(C)C1CCCCC1 FNZNHTIBNDAHFH-UHFFFAOYSA-N 0.000 description 1
- FCZQPWVILDWRBN-UHFFFAOYSA-N n'-cyclohexylethane-1,2-diamine Chemical compound NCCNC1CCCCC1 FCZQPWVILDWRBN-UHFFFAOYSA-N 0.000 description 1
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
- YZPMGCUOUVFLJC-UHFFFAOYSA-N n'-decylethane-1,2-diamine Chemical compound CCCCCCCCCCNCCN YZPMGCUOUVFLJC-UHFFFAOYSA-N 0.000 description 1
- FHKWCXVXPHXBAC-UHFFFAOYSA-N n'-decylpropane-1,3-diamine Chemical compound CCCCCCCCCCNCCCN FHKWCXVXPHXBAC-UHFFFAOYSA-N 0.000 description 1
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 description 1
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 1
- SLEYAGWXAGXUAS-UHFFFAOYSA-N n'-hexadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCNCCN SLEYAGWXAGXUAS-UHFFFAOYSA-N 0.000 description 1
- ADKFRZBUXRKWDL-UHFFFAOYSA-N n'-hexylethane-1,2-diamine Chemical compound CCCCCCNCCN ADKFRZBUXRKWDL-UHFFFAOYSA-N 0.000 description 1
- UUWPMNGNEAEOIR-UHFFFAOYSA-N n'-hexylpropane-1,3-diamine Chemical compound CCCCCCNCCCN UUWPMNGNEAEOIR-UHFFFAOYSA-N 0.000 description 1
- LMTSQIZQTFBYRL-UHFFFAOYSA-N n'-octadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCN LMTSQIZQTFBYRL-UHFFFAOYSA-N 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- UTPUPJKKYXJFPX-UHFFFAOYSA-N n'-octylethane-1,2-diamine Chemical compound CCCCCCCCNCCN UTPUPJKKYXJFPX-UHFFFAOYSA-N 0.000 description 1
- KPZNJYFFUWANHA-UHFFFAOYSA-N n'-octylpropane-1,3-diamine Chemical compound CCCCCCCCNCCCN KPZNJYFFUWANHA-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000010971 suitability test Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、塗料やインキのビヒクル等の有機溶媒中に高
濃度に且つ容易に安定に分散せしめることができ、粒子
凝集、結晶成長或いは液の増結現象のない易分散性銅フ
タロシアニン顔料組成物及びその製造方法に関するもの
である。Detailed Description of the Invention (Industrial Field of Application) The present invention can be easily and stably dispersed in organic solvents such as paint and ink vehicles at high concentrations, and can prevent particle aggregation, crystal growth or liquid dispersion. The present invention relates to an easily dispersible copper phthalocyanine pigment composition that does not cause the build-up phenomenon, and a method for producing the same.
（従来の技術）
従来、合成によって得られる粗製銅フタロシアニンは、
一般にその一次粒子か粗大であり、ビヒクル中に分散さ
せても低い着色力しか示さず、又色相的にも顔料適性に
欠けている。(Prior art) Conventionally, crude copper phthalocyanine obtained by synthesis is
In general, their primary particles are coarse, exhibit only low tinting power even when dispersed in a vehicle, and lack pigment suitability in terms of hue.
そのため粗製銅フタロシアニンを顔料としての適性を有
するような形態に転化させるための種々の方法が実施さ
れている。Various methods have therefore been implemented to convert crude copper phthalocyanine into a form suitable as a pigment.
従来実施されている方法としては、例えば、粗！！Ｉ鋼
フタロシアニンに食塩等の磨砕助剤を加え、少５［のイ
ｆＪ１溶剤の共存下ボールミル等で乾式磨砕処理を行な
う方法、又は粗製銅フタロシアニンを磨砕助剤及び有機
液体の存在下ニーダ−等で湿式磨砕処理する方法等が知
られている。Conventionally used methods include, for example, coarse! ! A method in which a grinding aid such as salt is added to I steel phthalocyanine and dry milling is carried out in a ball mill etc. in the presence of a small amount of IfJ1 solvent, or crude copper phthalocyanine is subjected to a dry grinding process in the presence of a grinding aid and an organic liquid. A method of wet grinding using a kneader or the like is known.
（発明が解決すべき問題点）
しかしながら、前記した顔料化処理によって得られた銅
フタロシアニン顔料は、特に塗料や印刷インキ用のワニ
ス或いは他の有機溶媒中において分散安定性や結晶安定
性が十分でなく、凝集が生じるため、液媒体の流動性、
グロスや着色力に優れた着色組成物が得られないもので
あった。(Problems to be Solved by the Invention) However, the copper phthalocyanine pigment obtained by the pigmentation treatment described above does not have sufficient dispersion stability or crystal stability, especially in varnishes for paints and printing inks, or other organic solvents. fluidity of the liquid medium, as agglomeration occurs.
A colored composition with excellent gloss and coloring power could not be obtained.
そのため粗製銅フタロシアニンを磨砕助剤及び有機液体
の共存下、湿式磨砕処理する方法においてフタルイミド
メチルフタロシアニンを添加して磨砕処理する方法く特
開昭５９−１０２９５８号公Ｎ）或いはアルキル硫酸エ
ステル等の界面活性剤を加えて処理する方法（特開昭５
９−１０２９５６号公報）等が知られている。Therefore, in a method of wet grinding crude copper phthalocyanine in the coexistence of a grinding aid and an organic liquid, a method of adding phthalimidomethyl phthalocyanine to the grinding process is proposed (Japanese Patent Application Laid-Open No. 59-102958 N) or an alkyl sulfate ester. A method of treatment by adding a surfactant such as
9-102956) and the like are known.
しかしながら、前記した方法によっても塗料や印刷イン
キ用のワニス或いは有機液体中においてＩ−分満足する
ことのできる流動性、グロス及び着色力を示すものが得
られていない。However, even with the above-mentioned methods, it has not been possible to obtain a material that exhibits fluidity, gloss, and coloring power that can satisfy the I-minute content in paints, varnishes for printing inks, or organic liquids.
本発明者等はこれら従来法の欠点を改善する方法につい
て説、０研究検討の結果、本発明に到達したものである
。The present inventors have arrived at the present invention as a result of research and study on ways to improve the shortcomings of these conventional methods.
（問題点を解決するための手段））
すなわち、本発明は、３発明からなり、第一の発明は、
銅フタロシアニン顔料、一般式（Ｉ）で表わされるフタ
ロシアニン誘導体及び硫酸エステル若しくは燐酸エステ
ルからなる易分散性銅フタロシアニン顔料組成物であり
、第二の発明は、粗製銅フタロシアニンを磨砕助剤、有
機液体、下記一般式（Ｉ）で表わされるフタロシアニン
誘導体及びｆ＆酸エステル若しくは燐酸ニス、チルの存
在下に磨砕処理することを特徴とする易分散性銅フタロ
シアニン顔料組成物の製造方法であり、第三の発明は、
粗製銅フタロシアニンを磨砕助剤、有機液体及び下記一
般式（Ｉ）で表わされるフタロシアニン誘導体の存在下
に磨砕処理し、該摩砕混合物に硫酸エステル若しくは燐
酸エステルを混合することを特徴とする易分散性銅フタ
ロシアニン顔料組成物の製造方法である。(Means for solving the problem)) That is, the present invention consists of three inventions, and the first invention is:
A readily dispersible copper phthalocyanine pigment composition comprising a copper phthalocyanine pigment, a phthalocyanine derivative represented by the general formula (I), and a sulfuric acid ester or a phosphoric acid ester, and the second invention is a composition comprising a copper phthalocyanine pigment, a phthalocyanine derivative represented by general formula (I), and a sulfuric acid ester or a phosphoric acid ester. , a method for producing an easily dispersible copper phthalocyanine pigment composition, which is characterized in that it is subjected to a grinding treatment in the presence of a phthalocyanine derivative represented by the following general formula (I) and an f& acid ester or a phosphoric acid varnish or chill; The invention of
Crude copper phthalocyanine is ground in the presence of a grinding aid, an organic liquid, and a phthalocyanine derivative represented by the following general formula (I), and a sulfuric acid ester or a phosphoric acid ester is mixed into the ground mixture. This is a method for producing an easily dispersible copper phthalocyanine pigment composition.
上記式中のＰｃは金属若しくは無金属フタロシアニン残
基を表わし、Ｘはメチレン基又はスルホニル基を表わし
、Ｒ５及びＲ２は水素原子又は置換若しくは未置換のア
ルキル基又はアリール基を表わし、Ｒ１とＲ２とは一緒
になって脂肪族環又は芳香族環を形成することができ、
ｎは１乃至４の整数を表わす。In the above formula, Pc represents a metal or metal-free phthalocyanine residue, X represents a methylene group or a sulfonyl group, R5 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group or aryl group, and R1 and R2 represent can be taken together to form an aliphatic or aromatic ring,
n represents an integer from 1 to 4.
（好ましい実施態様）
次に本発明を本発明の好ましい実施態様を挙げて更に詳
しく説明する。(Preferred Embodiments) Next, the present invention will be described in more detail by citing preferred embodiments of the present invention.
本発明において使用する粗製銅フタロシアニンとしては
、いずれの公知の粗製銅フタロシアニンでもよいが、例
えば、無水フタル酸若しくはその誘導体、尿素及び銅源
を、又はフタロジニトリル若しくはそのＬ’＋ＶＪ一体
及び銅源を触媒（例えば、モリブテン酸アンモニウム、
四塩化チタン等）の存在下若しくは不存在下に、有機液
体中で１２０乃至２７０℃、好ましくは１７０乃至２３
０℃で、２乃至１０時間、好ましくは３乃至７時間、常
圧叉は加圧下で反応させることによって製造されるもの
であり、これらの粗製銅フタロシアニンは！乃至２個の
ハロゲン環ｆを有してもよいものである。又、本発明に
おいて言う銅フタロシアニン顔料とはこれらの粗製銅フ
タロシアニンを常法に従って顔料化したものである。The crude copper phthalocyanine used in the present invention may be any known crude copper phthalocyanine; for example, phthalic anhydride or its derivatives, urea and a copper source, or phthalodinitrile or its L'+VJ integral and a copper source. catalyst (e.g. ammonium molybutate,
titanium tetrachloride, etc.) in an organic liquid at 120 to 270°C, preferably 170 to 23°C.
These crude copper phthalocyanines are produced by reacting at 0°C for 2 to 10 hours, preferably 3 to 7 hours, under normal pressure or increased pressure. It may have from 2 to 2 halogen rings f. Further, the copper phthalocyanine pigment referred to in the present invention is one obtained by converting these crude copper phthalocyanines into pigments according to a conventional method.
本発明において使用する前記＝・般式（Ｉ）の化合物は
、フタロシアニン核に１個若しくは２個のハロゲン原子
やスルホン酸基を有してもよい金属フタロシアニン又は
無金属フタロシアニンをクロルメチル化或いはクロルス
ルホン化して、１個乃至４個のクロルメチル基若しくは
クロルスルホニル基を有する誘導体とし、これにアンモ
ニア、脂肪族アミン、芳香族アミン、ペテロ環式アミン
等を反応させて（：ｌられるものである。クロルメチル
化及びクロルスルホン化はいずれも公知の方法で行うこ
ともでき、又、上記アミンとの反応も同様である。又、
上記の金属フタロシアニンとしては銅フタロシアニンが
好ましいものである。The compound of general formula (I) used in the present invention is a metal phthalocyanine or a metal-free phthalocyanine which may have one or two halogen atoms or sulfonic acid groups in the phthalocyanine nucleus, by chloromethylation or chlorsulfone. Chlormethyl Both the conversion and chlorosulfonation can be carried out by known methods, and the reaction with the above amines can also be carried out in the same manner.
Copper phthalocyanine is preferred as the metal phthalocyanine.
従って前記一般式（Ｉ）中のｎはｌ乃至４個の整数であ
り、Ｒ１及びＲ２は、
メチルアミン。Therefore, n in the general formula (I) is an integer of 1 to 4, and R1 and R2 are methylamine.
ジメチルアミン、
ジエチルアミン、
ジプロピルアミン、
ジブチルアミン、
ヘキシルアミン、
シクロヘキシルアミン、
Ｎ−メチルシクロヘキシルアミン、
オクチルアミン、
２−エチルヘキシルアミン、
デシルアミン、
ドデシルアミン、
オクタデシルアミン（ステアリルアミン）、ヘキサデシ
ルアミン（バルミチルアミン）、ピロリジン、
ピペリジン、
モルホリン、
チオモルホリン、
ピペラジン、
Ｎ′−アルキルピペラジン、例えば、
Ｎ′−エチルピペラジン、
２−ジエチルアミノエチルアミン、
２−ジプロピルアミノエチルアミン、
２−ジブチルアミノエチルアミン、
３−ジエチルアミノプロビルアミン、
３−シクロへキシルアミノプロピルアミン、３−（Ｎ−
メチル−Ｎ−シクロヘキシル）−プロピルアミン、
２−シクロへキシルアミノエチルアミン、２−（Ｎ−メ
チル−Ｎ−シクロへキシルアミノ）−エチルアミン、
３−へキシルアミノプロピルアミン、
３−オクチルアミノプロピルアミン、
３−（２’−エチルへキシルアミノ）−プロピルアミン
、
３−デシルアミノプロピルアミン、
３−ドデシルアミノプロピルアミン、
３−バルミチルアミノブロピルアミン、３−ステアリル
アミノプロピルアミン、２−へキシルアミノエチルアミ
ン、
２−オクチルアミノエチルアミン、
２−（２”−エチルへキシルアミノ）−エチルアミン、
２−デシルアミノエチルアミン、
２−ドデシルアミノエチルアミン、
２−パルミチルアミノエチルアミン、
２−ステアリルアミノエチルアミン、
２−アミノ−１−ジメチルアミノブタン、２−アミノ−
１−ジエチルアミノブタン、２−アミノ−２−ジブチル
アミノブタン、２−アミノ−１−ジメチルアミノヘキサ
ン、２−アミノ−１−ジエチルアミノヘキサン、２−ア
ミノ−１−ジプロピルアミノヘキサン、２−メチル−１
−アミノ−３−ジメチルアミノプロパン、
２−メチル−１−アミノ−３−ジエチルアミノプロパン
、
２−メチル−１−アミノ−３−ジプロピルアミノプロパ
ン。Dimethylamine, diethylamine, dipropylamine, dibutylamine, hexylamine, cyclohexylamine, N-methylcyclohexylamine, octylamine, 2-ethylhexylamine, decylamine, dodecylamine, octadecylamine (stearylamine), hexadecylamine (valmityl) amine), pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, N'-alkylpiperazine, such as N'-ethylpiperazine, 2-diethylaminoethylamine, 2-dipropylaminoethylamine, 2-dibutylaminoethylamine, 3-diethylaminopro Bylamine, 3-cyclohexylaminopropylamine, 3-(N-
Methyl-N-cyclohexyl)-propylamine, 2-cyclohexylaminoethylamine, 2-(N-methyl-N-cyclohexylamino)-ethylamine, 3-hexylaminopropylamine, 3-octylaminopropylamine, 3 -(2'-ethylhexylamino)-propylamine, 3-decylaminopropylamine, 3-dodecylaminopropylamine, 3-balmitylaminopropylamine, 3-stearylaminopropylamine, 2-hexylaminoethylamine, 2-octylaminoethylamine, 2-(2”-ethylhexylamino)-ethylamine, 2-decylaminoethylamine, 2-dodecylaminoethylamine, 2-palmitylaminoethylamine, 2-stearylaminoethylamine, 2-amino-1- dimethylaminobutane, 2-amino-
1-diethylaminobutane, 2-amino-2-dibutylaminobutane, 2-amino-1-dimethylaminohexane, 2-amino-1-diethylaminohexane, 2-amino-1-dipropylaminohexane, 2-methyl-1
-amino-3-dimethylaminopropane, 2-methyl-1-amino-3-diethylaminopropane, 2-methyl-1-amino-3-dipropylaminopropane.
２−メチル−１−アミノ−３−ジブチルアミノプロパン
、
４−ジメチルアミノ−１−アミノブタン、４−ジエチル
アミノ−１−アミノブタン、４−ジブチルアミノ−１−
アミノブタン、６−シメチルアミンー１−アミノヘキサ
ン、６−ジエチルアミノ−１−アミノヘキサン、４−ジ
エチルアミノ−１−メチルブチルアミン−（９）、
４−ジメチルアミノ−１−メチルブチルアミン−（１）
、
ピペラジン、Ｎ−メチルビペラジン、
アニリン、
アニリン誘導体、
ナフチルアミン等の残基である。2-Methyl-1-amino-3-dibutylaminopropane, 4-dimethylamino-1-aminobutane, 4-diethylamino-1-aminobutane, 4-dibutylamino-1-
Aminobutane, 6-dimethylamine-1-aminohexane, 6-diethylamino-1-aminohexane, 4-diethylamino-1-methylbutylamine-(9), 4-dimethylamino-1-methylbutylamine-(1)
, piperazine, N-methylbiperazine, aniline, aniline derivatives, naphthylamine, etc.
本発明で使用する硫酸エステル及び燐酸エステルとは、
従来、硫酸エステル型又は燐酸エステル１１ｊｌアニオ
ン系界面活性剤と称されているものであって、長鎖アル
コール、第２級アルコール、オレフィン、脂肪族エチレ
ングリコリド、ポリエチレングリコールのモノアルキル
エーテル、モノ脂肪酸エステル、フェノールエーテル或
いは置換フェノールエーテル等と、硫酸又は燐酸とのエ
ステル又はそのアンモニア、アミン、アルカリ金属等の
塩であり、このような（ｉｌｔ酸エステル又は燐酸エス
テル型アニオン系界面活性剤は多数のものが市場から人
手でき、いずれも本発明において使用することができる
。以下これらの物質を界面活性剤と称する。The sulfuric acid ester and phosphoric acid ester used in the present invention are:
These are conventionally called sulfuric acid ester type or phosphoric acid ester anionic surfactants, and include long chain alcohols, secondary alcohols, olefins, aliphatic ethylene glycolide, monoalkyl ethers of polyethylene glycol, and monofatty acid esters. , esters of phenol ethers or substituted phenol ethers, etc., and sulfuric acid or phosphoric acid, or their salts with ammonia, amines, alkali metals, etc.; These substances are commercially available and can be used in the present invention.These substances are hereinafter referred to as surfactants.
本発明の易分散性銅フタロシアニン顔料組成物は上記の
成分を必須成分とするが、該組成物で使用する前記一般
式（Ｉ）のフタロシアニン誘導体と前記界面活性剤の使
用モル比は１：０．１乃至１：２の範囲であり、好まし
くは１：０．５乃至１：１であり、これらの両者は酸塩
基の相互作用によって何等かの結合をしていると思われ
る。上記フタロシアニン誘導体と界面活性剤とは合計量
で銅フタアロシアニン顔料１００重量部当り約３乃至５
０重量部の割合で使用するのが好ましい。The easily dispersible copper phthalocyanine pigment composition of the present invention has the above-mentioned components as essential components, and the molar ratio of the phthalocyanine derivative of general formula (I) and the surfactant used in the composition is 1:0. The ratio is in the range of .1 to 1:2, preferably 1:0.5 to 1:1, and it is thought that these two bond in some way through acid-base interaction. The total amount of the above-mentioned phthalocyanine derivative and surfactant is about 3 to 5 parts per 100 parts by weight of the copper phthalocyanine pigment.
Preferably, it is used in a proportion of 0 parts by weight.
以上の如き本発明の顔料組成物は任意の方法で各成分を
混合することによって得られる。例えば、芥成分を個々
に粉砕して混合する方法、各成分を一緒に混合粉砕する
方法、各成分を一緒に有機液体や摩砕助剤の存在下に混
合摩砕する方法、各成分を順次混合する方法等であり、
使用する装置としてはニーダ−、ボールミル、エツジラ
ンナー、攪拌式ボールミル、サンドミル、振動ボールミ
ル等である。The pigment composition of the present invention as described above can be obtained by mixing the respective components by any method. For example, methods include grinding and mixing the pulp components individually, mixing and grinding each component together, mixing and grinding each component together in the presence of an organic liquid or a grinding aid, and grinding each component one after the other. A method of mixing, etc.
Apparatus used include a kneader, ball mill, edge runner, stirring ball mill, sand mill, vibrating ball mill, and the like.
特に好ましい１つの方法は、前記粗製銅フタロシアニン
を磨砕助剤、有機液体、前記一般式（Ｉ）で表わされる
フタロシアニン誘導体及び前記界面活性剤の存在下に磨
砕処理する方法である。One particularly preferred method is a method in which the crude copper phthalocyanine is ground in the presence of a grinding aid, an organic liquid, the phthalocyanine derivative represented by the general formula (I), and the surfactant.
本発明において使用される磨砕助剤としては、塩化ナト
リウム、硫酸ナトリウム及び塩化カルシウム等の水溶性
のものが挙げられ、これらは１種又は２種以上混合使用
してもよい。又磨砕助剤はｅめ粉砕機によって粉砕した
ものを使用した方がより有効である。Examples of the grinding aid used in the present invention include water-soluble ones such as sodium chloride, sodium sulfate, and calcium chloride, and these may be used alone or in a mixture of two or more. Furthermore, it is more effective to use a grinding aid that has been ground by an e-mill.
その使用量は目的とする顔料品質によって異なるが、粗
製の銅フタロシアニンに対し１乃至８ｆｆｌ；１：１倍
、好ましくは、１乃至４重量倍である。The amount used varies depending on the desired pigment quality, but is 1 to 8 ffl; 1:1 times, preferably 1 to 4 times by weight, relative to crude copper phthalocyanine.
本発明において使用する有機液体とは、少なくとも若干
なりとも水溶性を有するものが好ましく、例えば、好ま
しい例としてアルコール類、ポリオール類が挙げられる
。The organic liquid used in the present invention preferably has at least some water solubility, and preferable examples thereof include alcohols and polyols.
アルコール類としてはｎ−プロピルアルコール、ｎ−ブ
チルアルコール、イソプロピルアルコール等が挙げられ
る。Examples of alcohols include n-propyl alcohol, n-butyl alcohol, and isopropyl alcohol.
又、ポリオール類としては、例えば、エチレングリコー
ル、ジエチレングリコール、トリエチレングリコール、
テトラエチレングリコール、プロピレングリコール、ジ
プロピレングリコール、トリプロピレングリコール、テ
トラプロピレングリコール等が挙げられ、これらの１種
又は２種以上混合して使用される。In addition, examples of polyols include ethylene glycol, diethylene glycol, triethylene glycol,
Examples include tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, and tetrapropylene glycol, and these may be used alone or in combination of two or more.
有機液体の使用量は、磨砕助剤の使用量によって異なる
が、粗製の銅フタロシアニンに対して、一般的には５０
乃至１５０重量％の範囲である。The amount of organic liquid used varies depending on the amount of grinding aid used, but is generally 50% of the crude copper phthalocyanine.
It ranges from 150% by weight.
本発明をＦとして特徴付ける眞記一般式（Ｉ）のフタロ
シアニン誘導体と界面活性剤の合計の使用量は、粗製銅
フタロシアニン１００＋］ｊｉｉ１部に対して３乃至５
０重に部、好ましくは５乃至２０市４１部である。The total amount of the phthalocyanine derivative of the general formula (I) and the surfactant, which characterizes the present invention as F, is 3 to 5 per part of crude copper phthalocyanine 100+]jii.
0 parts, preferably 5 to 20 parts to 41 parts.
又、その添加時期は、最初から添加する方法又は磨砕途
中で添加する方法があるが、途中から添加する方法がよ
り効果的である。As for when to add it, there are two methods: adding it from the beginning or adding it during the grinding process, but it is more effective to add it during the grinding process.
又、別の好ましい方法は、粗製銅フタロシアニンを摩砕
助剤、有機液体及び前記一般式（Ｉ）のフタロシアニン
誘導体の存在下に摩砕処理し、その後に前記硫酸エステ
ル又はリン酸エステルを添加混合する方法である。Another preferred method is to mill crude copper phthalocyanine in the presence of a milling aid, an organic liquid, and the phthalocyanine derivative of general formula (I), and then add and mix the sulfuric acid ester or phosphoric acid ester. This is the way to do it.
摩砕処理は−・般的には常温乃至１５０℃で数時間乃至
数七時間行うことによってモ分な顔料組成物が得られる
。The milling treatment is generally carried out at room temperature to 150° C. for several hours to several seven hours to obtain a moist pigment composition.
磨砕後の銅フタロシアニン顔料組成物の取出は通常の方
法により行なわれる。すなわち、磨砕内容物を水又は稀
薄酸処理し、磨砕助剤及び有機液体を溶解し、必要に応
じて前記硫酸エステル又は燐酸エステルを添加混合し、
その処理物を濾過、水洗、乾燥することによって本発明
の易分散性銅フタロシアニン顔料組成物を得ることがで
きる。The copper phthalocyanine pigment composition after grinding is removed by a conventional method. That is, the grinding contents are treated with water or diluted acid, the grinding aid and organic liquid are dissolved, and the sulfuric acid ester or phosphoric acid ester is added and mixed as necessary,
The easily dispersible copper phthalocyanine pigment composition of the present invention can be obtained by filtering, washing with water, and drying the treated product.
以下、実施例により本発明を更に具体的に説明する。尚
、文中、部又は％とあるのは特に断りの無い限り重量基
準である。Hereinafter, the present invention will be explained in more detail with reference to Examples. In the text, parts or percentages are based on weight unless otherwise specified.
実施例１
２０００容量部の双腕型混和機に粗製銅フタロシアニン
１５０部（顔料純度９５％）、塩化ナトリウム粉末６０
０部及びジエチレングリコール１５０部を配合し、７０
℃で６時間混合岸砕する。Example 1 150 parts of crude copper phthalocyanine (pigment purity 95%) and 60 parts of sodium chloride powder were placed in a 2000-part double-arm mixer.
0 parts and 150 parts of diethylene glycol, 70 parts
Mix and crush for 6 hours at °C.
次いでこの混合物に、モノアミノメチル銅フタロシアニ
ン１５部と、界面活性剤ＧＡＦＡＣＲＭ−７１０（東邦
化学製、ポリオキシエチレンアルキルフェニルエーテル
燐酸エステル塩）１５部を加え、更に７０℃で３０分間
摩砕混練する。この混練物を！ｊ量の水に役人後７０℃
とし３０分間撹拌する。次いで濾過、水洗し、得られた
ウェットケーキを７０乃至８０℃で乾燥し、本発明の銅
フタロシアニン顔料組成物を得た。Next, 15 parts of monoaminomethyl copper phthalocyanine and 15 parts of surfactant GAFACRM-710 (manufactured by Toho Chemical, polyoxyethylene alkylphenyl ether phosphate ester salt) were added to this mixture, and the mixture was further milled and kneaded at 70°C for 30 minutes. . This mixture! J amount of water at 70℃ after the official
and stir for 30 minutes. The wet cake obtained by filtration and washing with water was then dried at 70 to 80°C to obtain a copper phthalocyanine pigment composition of the present invention.
Ｌ記で得られた顔料組成物について出版グラビアインキ
適性試験を行なったところ、インキビヒクル中で簡単な
混合操作によって容易に且つ均一高濃度に分散し、長期
間放置後も顔料の凝集、沈降、結晶成長及び液の増粘が
なく優れた分散安定性を保持していた。また該インキに
より得られた印刷物の光沢度を光沢計で測定した結果、
後記比較例１で得られた顔料組成物による印刷物の光沢
を標準（１００）とした時、本実施例で得られたー顔料
組成物による印刷物の光沢は１１０％であり、比較例と
比べて光沢及び鮮明度が優れたものであった。A publication gravure ink suitability test was conducted on the pigment composition obtained in Section L, and it was found that it was easily and uniformly dispersed in a high concentration by a simple mixing operation in an ink vehicle, and that even after being left for a long time, there was no agglomeration or sedimentation of the pigment. Excellent dispersion stability was maintained without crystal growth or thickening of the liquid. In addition, as a result of measuring the glossiness of printed matter obtained with the ink using a glossmeter,
When the gloss of the printed matter obtained from the pigment composition obtained in Comparative Example 1 described later is set as the standard (100), the gloss of the printed matter obtained from the pigment composition obtained in this example is 110%, which is higher than that of the comparative example. The gloss and clarity were excellent.
実施例２
２０００容Ｍ部の双腕型混和機に粗製銅フタロシアニン
（顔料純度９５％）１５０部、塩化ナトリウム粉末６０
０部及びジエチレングリコール１５０部を配合し、７０
℃で６時間混合摩砕する。Example 2 150 parts of crude copper phthalocyanine (pigment purity 95%) and 60 parts of sodium chloride powder were placed in a 2000 volume M part double-arm mixer.
0 parts and 150 parts of diethylene glycol, 70 parts
Mix and mill for 6 hours at °C.
次いでこの混合物にモノアミノメチル銅フタロシアニン
１５部を加え、更に７０℃で３０分間摩砕混練する。こ
の混練物に水を加え温度を７０℃として３０分間解膠す
る。Next, 15 parts of monoaminomethyl copper phthalocyanine was added to this mixture, and the mixture was further milled and kneaded at 70°C for 30 minutes. Water is added to this kneaded material, and the temperature is set at 70° C. and peptized for 30 minutes.
次いで濾過、水洗し、得られたウェットケーキの固形分
１５５部に界面活性剤（ＧＡＦＡＣＲＭ４１０、ポリオ
キシエチレンアルキルフェニルエーテル燐酸エステル塩
）１５部を加え７０℃にて３０分間撹拌を行なう。これ
を濾過、水洗し得られたウェットケーキを７０乃至８０
℃で乾燥し本発明の銅フタロシアニン顔料組成物を得た
。Next, the wet cake was filtered and washed with water, and 15 parts of a surfactant (GAFACRM410, polyoxyethylene alkylphenyl ether phosphate salt) was added to 155 parts of the solid content of the obtained wet cake, followed by stirring at 70°C for 30 minutes. This was filtered and washed with water, and the resulting wet cake was 70 to 80%
It was dried at ℃ to obtain a copper phthalocyanine pigment composition of the present invention.
このもののインキビヒクル中での分散性及び分散安定性
は実施例１と同様であり、又、印刷物の光沢度は実施例
１に準じて測定した結果、比較例１で得られた顔料を標
準（１００）とした時、本実施例で得られた顔料は１２
０％であり、光沢及び鮮明度が優れたものであった。The dispersibility and dispersion stability of this product in the ink vehicle were the same as in Example 1, and the gloss of the printed matter was measured according to Example 1. The pigment obtained in Comparative Example 1 was compared with the standard ( 100), the pigment obtained in this example was 12
0%, and the gloss and clarity were excellent.
実施例３
実施例２において界面活性剤であるＧＡＦＡＣＰＥ５１
０を２０部にして、他は実施例２と同様に処理して本発
明の銅フタロシアニン顔料組成物１６０部を得た。Example 3 GAFACPE51, a surfactant in Example 2
The copper phthalocyanine pigment composition of the present invention was obtained in the same manner as in Example 2 except that 160 parts of the copper phthalocyanine pigment composition of the present invention was obtained.
この実施例の顔料組成物について実施例１と同様に印刷
面の光沢を測定したところ、比較例１を１００とすると
、１１５％であった。又、インキビヒクルに対する分散
性及び分散安定性も実施例１と同様に優れたものであっ
た。When the gloss of the printed surface of the pigment composition of this example was measured in the same manner as in Example 1, it was 115%, taking Comparative Example 1 as 100. Further, the dispersibility and dispersion stability in the ink vehicle were also excellent as in Example 1.
実施例４
実施例２で使用した界面活性剤に代えて界面活性剤剤パ
イオニンＡ−２８（竹本油脂製、アルキルエーテル硫酸
エステル塩）１５部使用して、他は実施例２と同様にし
て処理して本発明の銅フタロシアニン顔料組成物１５５
部を得た。Example 4 In place of the surfactant used in Example 2, 15 parts of the surfactant Pionin A-28 (manufactured by Takemoto Yushi Co., Ltd., alkyl ether sulfate ester salt) was used, and the rest was treated in the same manner as in Example 2. Copper phthalocyanine pigment composition 155 of the present invention
I got the department.
実施例１と同様にして比較例１を標準（＋００）として
実施例２で得られた顔料組成物による印刷物の光沢度を
比較したところ、色調は同等であり、光沢度は１１４％
であった。When comparing the glossiness of the printed matter with the pigment composition obtained in Example 2 using Comparative Example 1 as the standard (+00) in the same manner as in Example 1, the color tone was the same and the glossiness was 114%.
Met.
比較例１
２０００容量部の双腕型混和機に粗製銅フタロシアニン
（顔料純度９５％）１５０部、塩化ナトリウム粉末６０
０部及びジエチレングリコール１５０部を配合し、７０
℃で６時間混合摩砕する。Comparative Example 1 150 parts of crude copper phthalocyanine (pigment purity 95%) and 60 parts of sodium chloride powder were placed in a 2000 volume part double-arm mixer.
0 parts and 150 parts of diethylene glycol, 70 parts
Mix and mill for 6 hours at °C.
次いでこの混合物に、モノアミノメチル銅フタロシアニ
ン１５部を加え、更に７０℃で３０分間混練する。これ
を濾過、水洗し、得られたウェットケーキを７０乃至８
０℃で乾燥し比較例の銅フタロシアニン顔料組成物を得
た。Next, 15 parts of monoaminomethyl copper phthalocyanine is added to this mixture, and the mixture is further kneaded at 70°C for 30 minutes. This is filtered, washed with water, and the resulting wet cake is
It was dried at 0°C to obtain a copper phthalocyanine pigment composition of a comparative example.
実施例５
２０００：２！晴部の双腕型混和機に粗製銅フタロシア
ニン（顔料純度９５％）１５０部、塩化ナトリウム粉末
６００部、ジエチレングリコール１５０部を配合し、７
０℃で６時間混合摩砕する。Example 5 2000:2! 150 parts of crude copper phthalocyanine (pigment purity 95%), 600 parts of sodium chloride powder, and 150 parts of diethylene glycol were mixed in a Harabe double-arm mixer, and 7
Mix and mill for 6 hours at 0°C.
次いでこの混合物に、モノスルホアミド銅フタロシアニ
ン１５部を加え、更に７０℃で３０分間混練する。この
混練物に水を加え温度を７０℃として３０分間解膠する
。Next, 15 parts of monosulfamide copper phthalocyanine is added to this mixture, and the mixture is further kneaded at 70°C for 30 minutes. Water is added to this kneaded material, and the temperature is set at 70° C. and peptized for 30 minutes.
次いで濾過、水洗し、得られたウェットケーキ１５５部
（固形分）に界面活性剤（実施例２と同じ）１５部を加
え７０℃にて３０分間撹拌を行なう。これを濾過及び水
洗し、得られたウェットケーキを７０乃至８０℃で乾燥
して本発明の銅フタロシアニン顔料組成物を得た。Next, the wet cake was filtered and washed with water, and 15 parts of a surfactant (same as in Example 2) was added to 155 parts (solid content) of the obtained wet cake, followed by stirring at 70° C. for 30 minutes. This was filtered and washed with water, and the obtained wet cake was dried at 70 to 80°C to obtain a copper phthalocyanine pigment composition of the present invention.
この顔料組成物から調製した印刷物の光沢度を光沢計で
測定した結果、比較例１で得られた顔料組成物による印
刷物を標準（１００）としたとき本実施例で得られた顔
料組成物の場合は１２０％で光沢及び鮮明度が優れたも
のであった。As a result of measuring the glossiness of the printed matter prepared from this pigment composition using a gloss meter, it was found that when the printed matter obtained from the pigment composition obtained in Comparative Example 1 was taken as a standard (100), the glossiness of the pigment composition obtained in this example was In the case of 120%, the gloss and sharpness were excellent.
実施例６乃至１５
実施例１における一般式（Ｉ）のフタロシアニン誘導体
に代えて、下記第１表のフタロシアニン誘導体を使用し
、他は実施例１と同様にして本発明の銅フタロシアニン
顔料組成物を得た。これらの顔料組成物も実施例１と同
様に優れた分散性及び分散安定性をイｆするものであっ
た。Examples 6 to 15 The copper phthalocyanine pigment composition of the present invention was prepared in the same manner as in Example 1, except that the phthalocyanine derivatives shown in Table 1 below were used in place of the phthalocyanine derivative of general formula (I) in Example 1. Obtained. Similar to Example 1, these pigment compositions also exhibited excellent dispersibility and dispersion stability.
γＪ １ Ｆも
”Ｎｏ、ＰｃＸ ＲＲｎ
６ Ｃｕ Ｃ１ｌ、 水Ａ
（メチル ２７ Ｇｕ （
：ｌｌ、 水素 エチル １８
Ｃｕ Ｃ１１２水Ａ冶
ブチル ３ｑｇｃｕ□ 水素
シクロヘキシル ２１Ｏ無 ＳＯ７メチル
ノニル ４ＩＩ
Ｃｕ ＳＯ２エチル ステアリル
１１２ Ｃｕ Ｓｏ、
プロピル メチル ２１３
Ｃｕ Ｓｏ□ 水素
ドデシル １１４ Ｃｕ
ＣＨ２水素 ３−ジエチルアミノ ｌプ
ロピル
１５ （：ｕ Ｃ１−１２メチル
フェニル ３実施例１６乃至２５
実施例２における界面活性剤に代えて、下記第２表の界
面活性剤を使用し、他は実施例２と同様にして本発明の
銅フタロシアニン顔料組成物を得た。これらの顔料組成
物も実施例２と同様に優れた分散性及び分散安定性を有
するものであった。γJ 1 F also “No, PcX RRn 6 Cu C1l, Water A
(Methyl 27 Gu (
:ll, hydrogen ethyl 18
Cu C112 Water Aji
Butyl 3qgcu□ Hydrogen
Cyclohexyl 21O-free SO7 Methyl Nonyl 4II
Cu SO2 Ethyl Stearyl
112 Cu So,
Propyl methyl 213
Cu So□ Hydrogen
Dodecyl 114 Cu
CH2 hydrogen 3-diethylamino l propyl 15 (:u C1-12 methyl
Phenyl 3 Examples 16 to 25 A copper phthalocyanine pigment composition of the present invention was obtained in the same manner as in Example 2 except that the surfactants shown in Table 2 below were used in place of the surfactant in Example 2. . Similar to Example 2, these pigment compositions also had excellent dispersibility and dispersion stability.
γＪ ２−ｉ゛ζ
′、” Ｎｏ、 ’ −（ｊ−１６バイオニ
ンへ−２５（行末泪＋１Ｆｔ製、 高級アルコール 硫
酸エステル塩）
１７ エマール４０パウダー （花王製、 高級
アルコールｆＩ！Ｌ酸エステル塩）
１８ エマール２０Ｇ（花王製、 高級アルコール
硫酸エステル塩）
１９ エマ−ルア１ （花王製、 高級アルコー
ルｆｆＬ酸塩）２０ ＧＡＦＡＣＲＥ−４１０
（東邦化学、 ポリオキシエチレンフルキルフェニルエ
ーテル 燐酸エステル塩）２１ ＧＡＦＡ（：
ＲＭ−５１０（東邦化学、 ポリオキシエチレンア
ルキルフェニルエーテル 燐酸エステル塩）２２
ＧＡＦＡＣＲ５−７１０（東邦化学、 ポリオキシ
エチレンアルキルエーテル 燐酸エステル塩）
２３ バイオニン＾−７１（行末油脂、 アルキ
ル燐酸エステル塩）２４ バイオニンＡ−７５（
行末油１指、 アルキルエーテ禰酸エステル塩）
２５ ７デカコール （：Ｓ−１３６１Ｅ （
旭電化、 ポリオキシエチレンアルキルフェニルエーテ
ル ｍＭエステル塩）（作用・効果）
以上の如き本発明によれば、本発明の銅フタロシアニン
顔料組成物は、各種塗料、印刷インキ等の有機ビヒクル
中に高濃度、均−且つ安定的に分散し、特に出版グラビ
アインキにおいてビヒクル中に高濃度、均−且つ安定的
に分散し、従来の顔料組成物を使用した場合には最高で
も分￥ｋｆｉ度が１２乃至１５重量％であったのに対し
、本発明では２５乃至４０重量％という高濃度であって
も］−分に分散し、且つ粒子の凝集、結晶成長及び液の
増粘現象が生じないものであった。更に本発明の顔料組
成物は発色性良好であり、従来の顔料組成物の１１０％
以上の優れた光沢のある印刷物を学えることができる。γJ 2-i゛ζ ′, "No, ' - (j-16 Bionin-25 (manufactured by Kao, higher alcohol sulfate ester salt) 17 Emar 40 powder (manufactured by Kao, higher alcohol fI!L acid ester salt) 18 Emar 20G (manufactured by Kao, higher alcohol sulfate ester salt) 19 Emar 1 (manufactured by Kao, higher alcohol ffL salt) 20 GAFACRE-410
(Toho Chemical, polyoxyethylene furkylphenyl ether phosphate ester salt) 21 GAFA (:
RM-510 (Toho Chemical, polyoxyethylene alkylphenyl ether phosphate ester salt) 22
GAFACR5-710 (Toho Chemical, polyoxyethylene alkyl ether phosphate ester salt) 23 Bionin^-71 (terminal oil, alkyl phosphate ester salt) 24 Bionin A-75 (
1 finger of oil at the end of the line, alkyl ether ester salt) 25 7 decacol (:S-1361E (
Asahi Denka, polyoxyethylene alkyl phenyl ether (mM ester salt) (action/effect) According to the present invention as described above, the copper phthalocyanine pigment composition of the present invention can be used at high concentrations in organic vehicles such as various paints and printing inks. , evenly and stably dispersed, particularly in a publication gravure ink, in a vehicle with a high concentration, uniformly and stably dispersed, and when using a conventional pigment composition, the minute kfi degree is at most 12 to 15% by weight, whereas in the present invention, even at a high concentration of 25 to 40% by weight, it can be dispersed within - minutes and does not cause particle aggregation, crystal growth, or liquid thickening phenomena. there were. Furthermore, the pigment composition of the present invention has good coloring properties, which is 110% that of conventional pigment compositions.
You can learn more about excellent glossy prints.
Claims (12)
わされるフタロシアニン誘導体及び硫酸エステル若しく
は燐酸エステルからなる易分散性銅フタロシアニン顔料
組成物。 ▲数式、化学式、表等があります▼（ I ） （上記式中のＰｃは金属若しくは無金属フタロシアニン
残基を表わし、Ｘはメチレン基又はスルホニル基を表わ
し、Ｒ＿１及びＲ＿２は水素原子又は置換若しくは未置
換のアルキル基又はアリール基を表わし、Ｒ＿１とＲ＿
２とは一緒になって脂肪族環又は芳香族環を形成するこ
とができ、ｎは１乃至４の整数を表わす。）(1) An easily dispersible copper phthalocyanine pigment composition comprising a copper phthalocyanine pigment, a phthalocyanine derivative represented by the following general formula (I), and a sulfuric acid ester or a phosphoric acid ester. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (Pc in the above formula represents a metal or metal-free phthalocyanine residue, X represents a methylene group or a sulfonyl group, and R_1 and R_2 are hydrogen atoms or substituted or unsubstituted Represents a substituted alkyl group or aryl group, R_1 and R_
2 can be taken together to form an aliphatic ring or an aromatic ring, and n represents an integer of 1 to 4. )
体である特許請求の範囲第（１）項に記載の易分散性銅
フタロシアニン顔料組成物。(2) The easily dispersible copper phthalocyanine pigment composition according to claim (1), wherein the compound of general formula (I) is a copper phthalocyanine derivative.
又はポリエチレングリコールモノエーテル若しくはモノ
エステルの硫酸エステルである特許請求の範囲第（１）
項に記載の易分散性銅フタロシアニン顔料組成物。(3) Claim No. 1, wherein the sulfuric ester is a sulfuric ester of a higher alcohol or a sulfuric ester of a polyethylene glycol monoether or monoester.
The easily dispersible copper phthalocyanine pigment composition described in 1.
又はポリエチレングリコールモノエーテル若しくはモノ
エステルの燐酸エステルである特許請求の範囲第（１）
項に記載の易分散性銅フタロシアニン顔料組成物。(4) Claim No. 1, wherein the phosphoric ester is a phosphoric ester of a higher alcohol or a phosphoric ester of a polyethylene glycol monoether or monoester.
The easily dispersible copper phthalocyanine pigment composition described in 1.
記一般式（ I ）で表わされるフタロシアニン誘導体及
び硫酸エステル若しくは燐酸エステルの存在下に磨砕処
理することを特徴とする易分散性銅フタロシアニン顔料
組成物の製造方法。 ▲数式、化学式、表等があります▼（ I ） （上記式中のＰｃは金属若しくは無金属フタロシアニン
残基を表わし、Ｘはメチレン基又はスルホニル基を表わ
し、Ｒ＿１及びＲ＿２は水素原子又は置換若しくは未置
換のアルキル基又はアリール基を表わし、Ｒ＿１とＲ＿
２とは一緒になって脂肪族環又は芳香族環を形成するこ
とができ、ｎは１乃至４の整数を表わす。）(5) Easily dispersible copper phthalocyanine characterized by grinding crude copper phthalocyanine in the presence of a grinding aid, an organic liquid, a phthalocyanine derivative represented by the following general formula (I), and a sulfuric acid ester or a phosphoric acid ester. A method for producing a pigment composition. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (Pc in the above formula represents a metal or metal-free phthalocyanine residue, X represents a methylene group or a sulfonyl group, and R_1 and R_2 are hydrogen atoms or substituted or unsubstituted Represents a substituted alkyl group or aryl group, R_1 and R_
2 can be taken together to form an aliphatic ring or an aromatic ring, and n represents an integer of 1 to 4. )
体である特許請求の範囲第（５）項に記載の易分散性銅
フタロシアニン顔料組成物の製造方法。(6) The method for producing a readily dispersible copper phthalocyanine pigment composition according to claim (5), wherein the compound of general formula (I) is a copper phthalocyanine derivative.
又はポリエチレングリコールモノエーテル若しくはモノ
エステルの硫酸エステルである特許請求の範囲第（５）
項に記載の易分散性銅フタロシアニン顔料組成物の製造
方法。(7) Claim No. 5, wherein the sulfuric ester is a sulfuric ester of a higher alcohol or a sulfuric ester of a polyethylene glycol monoether or monoester.
A method for producing an easily dispersible copper phthalocyanine pigment composition as described in 2.
又はポリエチレングリコールモノエーテル若しくはモノ
エステルの燐酸エステルである特許請求の範囲第（５）
項に記載の易分散性銅フタロシアニン顔料組成物の製造
方法。(8) Claim No. 5, wherein the phosphoric ester is a phosphoric ester of a higher alcohol or a phosphoric ester of a polyethylene glycol monoether or monoester.
A method for producing an easily dispersible copper phthalocyanine pigment composition as described in 2.
下記一般式（ I ）で表わされるフタロシアニン誘導体
の存在下に磨砕処理し、該摩砕混合物に硫酸エステル若
しくは燐酸エステルを混合することを特徴とする易分散
性銅フタロシアニン顔料組成物の製造方法。 ▲数式、化学式、表等があります▼（ I ） （上記式中のＰｃは金属若しくは無金属フタロシアニン
残基を表わし、Ｘはメチレン基又はスルホニル基を表わ
し、Ｒ＿１及びＲ＿２は水素原子又は置換若しくは未置
換のアルキル基又はアリール基を表わし、Ｒ＿１とＲ＿
２とは一緒になって脂肪族環又は芳香族環を形成するこ
とができ、ｎは１乃至４の整数を表わす。）(9) Grinding crude copper phthalocyanine in the presence of a grinding aid, an organic liquid, and a phthalocyanine derivative represented by the following general formula (I), and mixing a sulfuric acid ester or a phosphoric acid ester into the ground mixture. A method for producing a characterized easily dispersible copper phthalocyanine pigment composition. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (Pc in the above formula represents a metal or metal-free phthalocyanine residue, X represents a methylene group or a sulfonyl group, and R_1 and R_2 are hydrogen atoms or substituted or unsubstituted Represents a substituted alkyl group or aryl group, R_1 and R_
2 can be taken together to form an aliphatic ring or an aromatic ring, and n represents an integer of 1 to 4. )
導体である特許請求の範囲第（９）項に記載の易分散性
銅フタロシアニン顔料組成物の製造方法。(10) The method for producing a readily dispersible copper phthalocyanine pigment composition according to claim (9), wherein the compound of general formula (I) is a copper phthalocyanine derivative.
ル又はポリエチレングリコールモノエーテル若しくはモ
ノエステルの硫酸エステルである特許請求の範囲第（９
）項に記載の易分散性銅フタロシアニン顔料組成物の製
造方法。(11) Claim No. 9, wherein the sulfuric ester is a sulfuric ester of a higher alcohol or a sulfuric ester of a polyethylene glycol monoether or monoester.
) A method for producing an easily dispersible copper phthalocyanine pigment composition.
ル又はポリエチレングリコールモノエーテル若しくはモ
ノエステルの燐酸エステルである特許請求の範囲第（９
）項に記載の易分散性銅フタロシアニン顔料組成物の製
造方法。(12) The phosphoric ester is a phosphoric ester of a higher alcohol or a phosphoric ester of a polyethylene glycol monoether or monoester, Claim No. 9
) A method for producing an easily dispersible copper phthalocyanine pigment composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8117587A JPS63248864A (en) | 1987-04-03 | 1987-04-03 | Readily dispersible copper phthalocyanine pigment composition and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8117587A JPS63248864A (en) | 1987-04-03 | 1987-04-03 | Readily dispersible copper phthalocyanine pigment composition and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63248864A true JPS63248864A (en) | 1988-10-17 |
Family
ID=13739128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8117587A Pending JPS63248864A (en) | 1987-04-03 | 1987-04-03 | Readily dispersible copper phthalocyanine pigment composition and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63248864A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007131832A (en) * | 2005-10-14 | 2007-05-31 | Toyo Ink Mfg Co Ltd | Pigment composition |
| WO2014185471A1 (en) * | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| WO2014185475A1 (en) | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| WO2014185473A1 (en) * | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| US10012922B2 (en) | 2016-03-18 | 2018-07-03 | Canon Kabushiki Kaisha | Toner and method for producing toner |
| US10078285B2 (en) | 2016-03-18 | 2018-09-18 | Canon Kabushiki Kaisha | Toner and method for manufacturing toner |
| US10295922B2 (en) | 2016-03-18 | 2019-05-21 | Canon Kabushiki Kaisha | Toner and toner manufacturing method |
| WO2022202208A1 (en) * | 2021-03-24 | 2022-09-29 | 株式会社Ｄｎｐファインケミカル | Color material liquid dispersion, modified color material, curable coloring composition, color filter, and display device |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5462227A (en) * | 1977-10-28 | 1979-05-19 | Toyo Ink Mfg Co Ltd | Phthalocyanine pigment composition |
-
1987
- 1987-04-03 JP JP8117587A patent/JPS63248864A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5462227A (en) * | 1977-10-28 | 1979-05-19 | Toyo Ink Mfg Co Ltd | Phthalocyanine pigment composition |
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|---|---|---|---|---|
| JP2007131832A (en) * | 2005-10-14 | 2007-05-31 | Toyo Ink Mfg Co Ltd | Pigment composition |
| JPWO2014185473A1 (en) * | 2013-05-14 | 2017-02-23 | 花王株式会社 | Method for producing fine organic pigment |
| CN105229085A (en) * | 2013-05-14 | 2016-01-06 | 花王株式会社 | The manufacture method of fine pigment dyestuff |
| JPWO2014185475A1 (en) * | 2013-05-14 | 2017-02-23 | 花王株式会社 | Method for producing fine organic pigment |
| CN105209553A (en) * | 2013-05-14 | 2015-12-30 | 花王株式会社 | Production method for fine organic pigment |
| US9663676B2 (en) | 2013-05-14 | 2017-05-30 | Kao Corporation | Production method for fine organic pigment |
| CN105229086A (en) * | 2013-05-14 | 2016-01-06 | 花王株式会社 | The manufacture method of fine pigment dyestuff |
| JPWO2014185471A1 (en) * | 2013-05-14 | 2017-02-23 | 花王株式会社 | Method for producing fine organic pigment |
| US9752033B2 (en) | 2013-05-14 | 2017-09-05 | Kao Corporation | Production method for fine organic pigment |
| WO2014185473A1 (en) * | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| WO2014185475A1 (en) | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| WO2014185471A1 (en) * | 2013-05-14 | 2014-11-20 | 花王株式会社 | Production method for fine organic pigment |
| US9783680B2 (en) | 2013-05-14 | 2017-10-10 | Kao Corporation | Production method for fine organic pigment |
| EP2998363B1 (en) * | 2013-05-14 | 2018-09-19 | Kao Corporation | Production method for fine organic pigment |
| US10078285B2 (en) | 2016-03-18 | 2018-09-18 | Canon Kabushiki Kaisha | Toner and method for manufacturing toner |
| US10012922B2 (en) | 2016-03-18 | 2018-07-03 | Canon Kabushiki Kaisha | Toner and method for producing toner |
| US10295922B2 (en) | 2016-03-18 | 2019-05-21 | Canon Kabushiki Kaisha | Toner and toner manufacturing method |
| WO2022202208A1 (en) * | 2021-03-24 | 2022-09-29 | 株式会社Ｄｎｐファインケミカル | Color material liquid dispersion, modified color material, curable coloring composition, color filter, and display device |
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