JP3931654B2 - Pigment composition and pigment dispersion - Google Patents
Pigment composition and pigment dispersion Download PDFInfo
- Publication number
- JP3931654B2 JP3931654B2 JP2001395669A JP2001395669A JP3931654B2 JP 3931654 B2 JP3931654 B2 JP 3931654B2 JP 2001395669 A JP2001395669 A JP 2001395669A JP 2001395669 A JP2001395669 A JP 2001395669A JP 3931654 B2 JP3931654 B2 JP 3931654B2
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- JP
- Japan
- Prior art keywords
- group
- formula
- optionally substituted
- pigment
- derivative
- 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.)
- Expired - Fee Related
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- 239000000049 pigment Substances 0.000 title claims description 102
- 239000006185 dispersion Substances 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 15
- 239000000178 monomer Substances 0.000 claims description 35
- 229920001577 copolymer Polymers 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000003918 triazines Chemical class 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000007334 copolymerization reaction Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000012860 organic pigment Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- -1 sodium and potassium Chemical class 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 20
- 239000000975 dye Substances 0.000 description 19
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 13
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 12
- 239000000976 ink Substances 0.000 description 12
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 11
- 229920001223 polyethylene glycol Polymers 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 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 8
- 150000004056 anthraquinones Chemical class 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000000460 chlorine Chemical group 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920001515 polyalkylene glycol Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- KQBTUOVABZLXGP-UHFFFAOYSA-N butane-1,4-diol;ethane-1,2-diol Chemical compound OCCO.OCCCCO KQBTUOVABZLXGP-UHFFFAOYSA-N 0.000 description 4
- DDPAAMHROJBRGE-UHFFFAOYSA-N butane-1,4-diol;propane-1,2-diol Chemical compound CC(O)CO.OCCCCO DDPAAMHROJBRGE-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- PVMCQBPJKPMOKM-UHFFFAOYSA-N 1-cyclopentylpiperazine Chemical compound C1CCCC1N1CCNCC1 PVMCQBPJKPMOKM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 238000006149 azo coupling reaction Methods 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 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 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 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 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
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- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 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
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- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-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
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
- HFOVYSKOTZHZRV-UHFFFAOYSA-N n,n-bis(ethylamino)butan-1-amine Chemical compound CCCCN(NCC)NCC HFOVYSKOTZHZRV-UHFFFAOYSA-N 0.000 description 1
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- DVFVBAPHBZWJFX-UHFFFAOYSA-N n-(2-methylpropyl)butan-2-amine Chemical compound CCC(C)NCC(C)C DVFVBAPHBZWJFX-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- XQOIBQBPAXOVGP-UHFFFAOYSA-N n-ethyl-2-methylpropan-2-amine Chemical compound CCNC(C)(C)C XQOIBQBPAXOVGP-UHFFFAOYSA-N 0.000 description 1
- BTCXINMWPKVQNR-UHFFFAOYSA-N n-ethyl-n'-hexylethane-1,2-diamine Chemical compound CCCCCCNCCNCC BTCXINMWPKVQNR-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
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- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
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- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- QYNZYUUXSVZDJO-UHFFFAOYSA-N n-propylbutan-2-amine Chemical compound CCCNC(C)CC QYNZYUUXSVZDJO-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
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- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
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- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Description
【０００１】
【発明の属する技術分野】
本発明は、使用適性、特に非集合性、流動性に優れた顔料組成物および顔料分散体に関する。
【０００２】
【従来の技術】
一般に、顔料の微細な粒子をオフセットインキ、グラビアインキおよび塗料のようなビヒクルに分散する場合、安定な分散体を得ることが難しく、製造作業上および得られる製品の価値に種々の問題を引き起こすことが知られている。
例えば、微細な粒子からなる顔料を含む分散体は、往々にして高粘度を示し、製品の分散機からの取り出し、輸送が困難となるばかりでなく、更に悪い場合は貯蔵中にゲル化を起こし使用困難となることがある。さらに、展色物の塗膜表面に関しては、光沢の低下、レベリング不良等の状態不良を生じることがある。また、異種の顔料を混合して使用する場合、凝集による色別れや、沈降などの現象により展色物に色むらや著しい着色力の低下が現れることがある。
【０００３】
以上のような種々の問題点を解決するために、有機顔料を母体骨格として側鎖に酸性基や塩基性基を置換基として有する顔料誘導体を分散剤として混合する方法が、特公昭４１−２４６６号公報、ＵＳＰ２８５５４０３号公報、特開昭６３−３０５１７３号公報、特開平１−２４７４６８号公報、特開平３−２６７６７号公報等に開示されている。また、無機材料に対する使用が、特開平１１−１０４４７９号公報、特開平１１−１１６２３８号公報等に開示されている。
しかし、すべての材料に有効ではなく、特に、有機顔料に対しては、良好な分散体は得られない。また、塗料、インキ等には非常に多くのワニス系が存在するため、これらの方法を用いても一部のワニス系を除いては満足な効果が得られていないのが実状である。
【０００４】
【発明が解決しようとする課題】
そこで、本発明は、オフッセトインキ、グラビアインキ、塗料、インキジェットインキ等に適する非集合性、流動性に優れた安定な顔料組成物および顔料分散体の提供を目的とする。
【０００５】
【課題を解決するための手段】
本発明者らは、塩基性基を有する、顔料誘導体、アントラキノン誘導体、アクリドン誘導体またはトリアジン誘導体と、リン酸基を有する単量体およびアルキレンオキサイド鎖を有する単量体を共重合成分として含む共重合体とを併用することにより、顔料分散性が飛躍的に改善することを見出し、本発明に至った。
すなわち、本発明は、塩基性基を有する顔料誘導体、塩基性基を有するアントラキノン誘導体、塩基性基を有するアクリドン誘導体または塩基性基を有するトリアジン誘導体から選ばれる少なくとも一種、リン酸基を有するエチレン性不飽和単量体と下記式（１）で示されるエチレン性不飽和単量体とを共重合成分として含む共重合体、及び顔料を含んでなることを特徴とする顔料組成物に関する。
また、本発明は、前記顔料組成物をワニスに分散せしめてなる顔料分散体に関する。
【０００６】
式（１）
【化８】
Ｒ2 : 炭素数２〜４アルキレン基を表す。
Ｒ3 : 水素原子、炭素数１〜３０のアルキル基、-CH2-CH=CH2、置換基を有していてもよいフェニル基または-C(=0)-C(R1)=CH2 を表す。
ｎ ：２〜１００の整数を表す。
【０００７】
本発明のリン酸基を有するエチレン性不飽和単量体と下記式（１）で示されるエチレン性不飽和単量体とを共重合成分として含む共重合体は、リン酸基を有するエチレン性不飽和単量体、式（１）で示されるエチレン性不飽和単量体、および必要に応じて前記単量体以外のエチレン性不飽和単量体をラジカル重合することにより得られる共重合体である。
【０００８】
リン酸基を有するエチレン性不飽和単量体は、リン酸基およびエチレン性不飽和二重結合を有する化合物であり、リン酸基は、下記式（８）で示される２価のリン酸基であっても、下記式（９）で示される１価のリン酸基であってもよい。また、リン酸基は、ナトリウム、カリウム等の金属、またはジエチルアミン、ジブチルアミン、トリエタノールアミン、エチルアミン、プロピルアミン、ブチルアミン、ペンチルアミン、ヘキシルアミン、オクチルアミン、ドデシルアミン、ステアリルアミン、オレイルアミン、ジステアリルアミン等の有機アミンと塩を形成していてもよい。
【０００９】
式（８）
【化９】
【化１０】
リン酸基を有するエチレン性不飽和単量体としては、例えば、エチレングリコールメタクリレートフォスフェート、プロピレングリコールメタクリレートフォスフェート、エチレングリコールアクリレートフォスフェート、プロピレングリコールアクリレートフォスフェートに代表されるような、下記一般式（１０）で示される化合物が挙げられる。
式（１０）
【化１１】
Ｒ14：アルキレン基を表す。
l：１〜２０の整数を表す。
【００１１】
リン酸基を有するエチレン性不飽和単量体の具体例を以下に示すが、これに限るものではない。
【化１２】
【化１４】
これらのリン酸基を有するエチレン性不飽和単量体は、特公昭５０−２２５３６号公報、特開昭５８−１２８３９３号公報等に記載の方法で製造することができる。市販品としては、ホスマーＭ、ホスマーＣＬ、ホスマーＰＥ、ホスマーＭＨ（以上、ユニケミカル社製）、ライトエステルＰ−１Ｍ（以上、共栄社化学社製）、ＪＡＭＰ−５１４（以上、城北化学工業社製）、ＫＡＹＡＭＥＲ ＰＭ−２、ＫＡＹＡＭＥＲ ＰＭ−２１（以上、日本化薬社製）等が挙げられる。
【００１４】
これらのリン酸基を有するエチレン性不飽和単量体は、単独あるいは２種以上の組み合わせで用いることができる。また、共重合体におけるリン酸基を有するエチレン性不飽和単量体の共重合比は、共重合体を構成する全ての単量体の合計１００重量部に対して、０．１〜３０重量部であることが好ましく、０．１〜５重量部であることが更に好ましい。
【００１５】
また、式（１）で示されるエチレン性不飽和単量体のうち、Ｒ3 が水素原子である水酸基末端ポリアルキレングリコールモノ（メタ）アクリレートとしては、例えば、ポリエチレングリコールモノメタクリレート、ポリエチレングリコールモノアクリレート、ポリプロピレングリコールモノメタクリレート、ポリプロピレングリコールモノアクリレート、ポリ（エチレングリコール-プロピレングリコール）モノメタクリレート、ポリエチレングリコール-ポリプロピレングリコールモノメタクリレート、ポリエチレングリコール-ポリプロピレングリコールモノアクリレート、ポリ（エチレングリコール-テトラメチレングリコール）モノメタクリレート、ポリ（エチレングリコール-テトラメチレングリコール）モノアクリレート、ポリ（プロピレングリコール-テトラメチレングリコール）モノメタアクリレート、ポリ（プロピレングリコール-テトラメチレングリコール）モノアクリレート、プロピレングリコールポリテトラメチレングリコールモノメタクリレート、プロピレングリコールポリテトラメチレングリコールモノアクリレートが挙げられる。
【００１６】
Ｒ3 が炭素数１〜３０のアルキル基であるアルキル基末端ポリアルキレングリコールモノ（メタ）アクリレートとしては、例えば、メトキシポリエチレングリコールモノメタクリレート、メトキシポリエチレングリコールモノアクリレート、オクトキシポリエチレングリコールモノアクリレート、オクトキシポリエチレングリコールポリプロピレングリコールモノメタクリレート、オクトキシポリエチレングリコールポリプロピレングリコールモノアクリレート、ラウロキシポリエチレングリコールモノアクリレート、ラウロキシポリエチレングリコールモノアクリレート、ステアロキシポリエチレングリコールモノメタクリレート、ステアロキシポリエチレングリコール-ポリプロピレングリコールモノアクリレート等が挙げられる。
【００１７】
Ｒ3 が-CH2-CH=CH2である、アリル基末端ポリアルキレングリコールモノ（メタ）アクリレートとしては、例えば、アリロキシポリエチレングリコール-ポリプロピレングリコールモノメタクリレート、アリロキシポリエチレングリコール-ポリプロピレングリコールモノアクリレート等が挙げられる。
Ｒ3 が置換基を有していてもよいフェニル基である、フェニル基末端ポリアルキレングリコールモノ（メタ）アクリレートとしては、例えば、ノニルフェノキシポリエチレングリコールモノアクリレート、ノニルフェノキシポリエチレングリコール-ポリプロピレングリコールモノメタクリレート、ノニルフェノキシポリプロピレングリコール-ポリエチレングリコールモノメタクリレート、ノニルフェノキシポリ（エチレングリコール-プロピレングリコール）モノアクリレート、フェノールＥＯ変性アクリレート、ノニルフェノールＥＯ変性アクリレート等が挙げられる。
【００１８】
Ｒ3 が-C(=0)-C(R1)=CH2 である、両末端（メタ）アクリロイル基のポリアルキレングリコールモノ（メタ）アクリレートとしては、例えば、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、ポリエチレングリコールジメタクリレート、ポリエチレングリコールジアクリレート、ポリプロピレングリコールジメタクリレート、ポリプロピレングリコールジアクリレート、ポリテトラメチレングリコールジメタクリレート、ポリテトラメチレングリコールジアクリレート、ポリ（エチレングリコール-テトラメチレングリコール）ジメタクリレート、ポリ（エチレングリコール-テトラメチレングリコール）ジアクリレート、ポリ（プロピレングリコール-テトラメチレングリコール）ジメタクリレート、ポリ（プロピレングリコール-テトラメチレングリコール）ジアクリレート、ポリエチレングリコール-ポリプロピレングリコール-ポリエチレングリコールジアクリレート等が挙げられる。
【００１９】
これらの単量体は、例えば日本油脂株式会社よりブレンマーシリーズや東亜合成株式会社よりアロニックスシリーズとして市販されている。
式（１）で示されるエチレン性不飽和単量体は、単独あるいは２種以上の組み合わせで用いることができる。また、共重合体における式（１）で示されるエチレン性不飽和単量体の共重合比は、共重合体を構成する全ての単量体の合計１００重量部に対して、０．１〜５０重量部であることが好ましい。
【００２０】
リン酸基を有するエチレン性不飽和単量体または式（１）で示されるエチレン性不飽和単量体以外の（他の）エチレン性不飽和単量体としては、アクリル酸メチル、アクリル酸エチル、アクリル酸ブチル、アクリル酸−２−エチルヘキシル、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸ブチル、メタクリル酸−２−エチルヘキシル、メタクリル酸オクチル、メタクリル酸ステアリル、メタクリル酸シクロヘキシル、メタクリル酸ベンジル等の（メタ）アクリル酸アルキルエステル類や、スチレン、α−メチルスチレン、ビニルトルエン、酢酸ビニル、プロピオン酸ビニルアクリル酸、２−ヒドロキシエチル（メタ）アクリレート、３−ヒドロキシプロピル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、３−ヒドロキシブチル（メタ）アクリレート、２−ヒドロキシブチル（メタ）アクリレート、グリセリン（メタ）アクリレート、ポリカプロラクトン変性ヒドロキシエチル（メタ）アクリレート（ｎ＝1〜６）、エポキシ（メタ）アクリレート、水酸基末端ウレタン（メタ）アクリレート等が挙げられる。
【００２１】
また、他のエチレン性不飽和単量体は、分子内に少なくとも１つのカルボキシル基を有するエチレン性不飽和単量体であってもよく、例えば、アクリル酸、メタクリル酸、２−カルボキシエチルアクリレート、フタル酸モノヒドロキシエチルアクリレート、ω−カルボキシ−ポリカプロラクトンモノアクリレート、マレイン酸、イタコン酸、フマル酸、グルタコン酸、テトラヒドロフタル酸等が挙げられる。これらは、１種または２種以上組み合わせて用いることができる。なお、分子内に少なくとも１つのカルボキシル基を有するエチレン性不飽和単量体を共重合成分として含む場合は、該単量体の共重合比は、共重合体を構成する全ての単量体の合計１００重量部に対して、１〜５０重量部であることが好ましい。
【００２２】
本発明の共重合体の重量平均分子量（Ｍｗ）は、分散性が良好な点から、好ましくは１０００〜１０００００であり、更に好ましくは５０００〜３００００である。
本発明の共重合体の合成は、開始剤の存在下、不活性ガス気流下、５０〜１５０℃で２〜１０時間かけて行われる。必要に応じて、溶剤の存在下で行っても差し支えない。
【００２３】
開始剤としては、ベンゾイルパーオキサイド、クメンヒドロパーオキサイド、ｔ−ブチルヒドロパーオキサイド、ジイソプロピルパーオキシカーボネート、ジｔ−ブチルパーオキサイド、ｔ−ブチルパーオキシベンゾエート等の有機過酸化物、２，２’−アゾビスイソブチロニトリル等のアゾ化合物等が挙げられる。開始剤は、エチレン性不飽和単量体の合計１００重量部に対して、好ましくは１〜２０重量部使用される。
【００２４】
溶剤としては、水および/または水混和性有機溶剤、またはエチルセルソルブアセテート、プロピレングリコールモノメチルエーテルアセテートなどの酢酸エステル；シクロヘキサノン、メチルイソブチルケトンなどのケトン類；キシレン、エチルベンゼンなどを用いることができる。水混和性有機溶剤としては、エチルアルコール、イソプロピルアルコール、n-プロピルアルコール等のアルコール系溶剤や、エチレングリコールまたはジエチレングリコールのモノまたはジアルキルエーテル等が挙げられる。
【００２５】
本発明を構成する、塩基性基を有する顔料誘導体、塩基性基を有するアントラキノン誘導体、塩基性基を有するアクリドン誘導体または塩基性基を有するトリアジン誘導体は、下記一般式（２）、（３）、（４）および（５）で示される群から選ばれる少なくとも１つの置換基を有するものである。
式（２）
【化１７】
式（３）
【化１８】
【化１９】
【化２０】
Ｘ：−ＳＯ2−、−ＣＯ−、−ＣＨ2ＮＨＣＯＣＨ2−、−ＣＨ2−または直接結合を表す。
ｍ：１〜１０の整数を表す。
Ｒ4 、Ｒ5 ：それぞれ独立に、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、置換されていてもよいフェニル基、またはＲ4 とＲ5 とで一体となって更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を表す。アルキル基およびアルケニル基の炭素数は１〜１０が好ましい。
Ｒ6 ：置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。アルキル基およびアルケニル基の炭素数は１〜１０が好ましい。
Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10：それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。アルキル基およびアルケニル基の炭素数は１〜５が好ましい。
【００２８】
Ｙ：−ＮＲ11−Ｚ−ＮＲ12−または直接結合を表す。
Ｒ11、Ｒ12：それぞれ独立に水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。アルキル基およびアルケニル基の炭素数は１〜５が好ましい。
Ｚ：置換されていてもよいアルキレン基、置換されていてもよいアルケニレン基または置換されていてもよいフェニレン基を表す。アルキル基およびアルケニル基の炭素数は１〜８が好ましい。
Ｐ：式（６）で示される置換基または式（７）で示される置換基を表す。
Ｑ：水酸基、アルコキシル基、式（６）で示される置換基または式（７）で示される置換基を表す。
【００２９】
式（６）
【化２１】
【化２２】
式（２）〜式（７）で示される置換基を形成するために使用されるアミン成分としては、例えば、ジメチルアミン、ジエチルアミン、Ｎ，Ｎ−エチルイソプロピルアミン、Ｎ，Ｎ−エチルプロピルアミン、Ｎ，Ｎ−メチルブチルアミン、Ｎ，Ｎ−メチルイソブチルアミン、Ｎ，Ｎ−ブチルエチルアミン、Ｎ，Ｎ−ｔｅｒｔ−ブチルエチルアミン、ジイソプロピルアミン、ジプロピルアミン、Ｎ，Ｎ−ｓｅｃ−ブチルプロピルアミン、ジブチルアミン、ジーｓｅｃ−ブチルアミン、ジイソブチルアミン、Ｎ，Ｎ−イソブチル−ｓｅｃ−ブチルアミン、ジアミルアミン、ジイソアミルアミン、ジヘキシルアミン、ジ（２−エチルへキシル）アミン、ジオクチルアミン、Ｎ，Ｎ−メチルオクタデシルアミン、ジデシルアミン、ジアリルアミン、Ｎ，Ｎ−エチル−１，２−ジメチルプロピルアミン、Ｎ，Ｎ−メチルヘキシルアミン、ジオレイルアミン、ジステアリルアミン、Ｎ，Ｎ−ジメチルアミノメチルアミン、Ｎ，Ｎ−ジメチルアミノエチルアミン、Ｎ，Ｎ−ジメチルアミノアミルアミン、Ｎ，Ｎ−ジメチルアミノブチルアミン、Ｎ，Ｎ−ジエチルアミノエチルアミン、Ｎ，Ｎ−ジエチルアミノプロピルアミン、Ｎ，Ｎ−ジエチルアミノヘキシルアミン、Ｎ，Ｎ−ジエチルアミノブチルアミン、Ｎ，Ｎ−ジエチルアミノペンチルアミン、Ｎ，Ｎ−ジプロピルアミノブチルアミン、Ｎ，Ｎ−ジブチルアミノプロピルアミン、Ｎ，Ｎ−ジブチルアミノエチルアミン、Ｎ，Ｎ−ジブチルアミノブチルアミン、Ｎ，Ｎ−ジイソブチルアミノペンチルアミン、Ｎ，Ｎ−メチルーラウリルアミノプロピルアミン、Ｎ，Ｎ−エチルーヘキシルアミノエチルアミン、Ｎ，Ｎ−ジステアリルアミノエチルアミン、Ｎ，Ｎ−ジオレイルアミノエチルアミン、Ｎ，Ｎ−ジステアリルアミノブチルアミン、ピペリジン、２−ピペコリン、３−ピペコリン、４−ピペコリン、２，４−ルペチジン、２，６−ルペチジン、３，５−ルペチジン、３−ピペリジンメタノール、ピペコリン酸、イソニペコチン酸、イソニコペチン酸メチル、イソニコペチン酸エチル、２−ピペリジンエタノール、ピロリジン、３−ヒドロキシピロリジン、Ｎ−アミノエチルピペリジン、Ｎ−アミノエチル−４−ピペコリン、Ｎ−アミノエチルモルホリン、Ｎ−アミノプロピルピペリジン、Ｎ−アミノプロピル−２−ピペコリン、Ｎ−アミノプロピル−４−ピペコリン、Ｎ−アミノプロピルモルホリン、Ｎ−メチルピペラジン、Ｎ−ブチルピペラジン、Ｎ−メチルホモピペラジン、１−シクロペンチルピペラジン、１−アミノ−４−メチルピペラジン、１−シクロペンチルピペラジン等が挙げられる。
【００３１】
塩基性基を有する顔料誘導体を構成する有機色素は、例えば、ジケトピロロピロール系色素、アゾ、ジスアゾ、ポリアゾ等のアゾ系色素、フタロシアニン系色素、ジアミノジアントラキノン、アントラピリミジン、フラバントロン、アントアントロン、インダントロン、ピラントロン、ビオラントロン等のアントラキノン系色素、キナクリドン系色素、ジオキサジン系色素、ペリノン系色素、ペリレン系色素、チオインジゴ系色素、イソインドリン系色素、イソインドリノン系色素、キノフタロン系色素、スレン系色素、金属錯体系色素等の色素である。
また、塩基性基を有するアントラキノン誘導体および塩基性基を有するアクリドン誘導体は、メチル基、エチル基等のアルキル基、アミノ基、ニトロ基、水酸基またはメトキシ基、エトキシ基等のアルコキシ基または塩素等のハロゲン等の置換基を有していてもよい。
【００３２】
また、塩基性基を有するトリアジン誘導体は、メチル基、エチル基等のアルキル基、アミノ基またはジメチルアミノ基、ジエチルアミノ基、ジブチルアミノ基等のアルキルアミノ基、ニトロ基、水酸基またはメトキシ基、エトキシ基、ブトキシ基等のアルコキシ基、塩素等のハロゲン、またはメチル基、メトキシ基、アミノ基、ジメチルアミノ基、水酸基等で置換されていてもよいフェニル基、またはメチル基、エチル基、メトキシ基、エトキシ基、アミノ基、ジメチルアミノ基、ジエチルアミノ基、ニトロ基、水酸基等で置換されていてもよいフェニルアミノ基等の置換基を有していてもよい１，３，５−トリアジンである。
【００３３】
本発明の塩基性基を有する顔料誘導体およびアントラキノン誘導体は、種々の合成経路で合成することができる。例えば、有機色素もしくはアントラキノンに式（１１）〜式（１４）で示される置換基を導入した後、上記置換基と反応して式（２）〜式（５）で示される置換基を形成するアミン成分、例えば、Ｎ，Ｎ−ジメチルアミノプロピルアミン、Ｎ−メチルピペラジン、ジエチルアミンまたは４−［４−ヒドロキシ−６−［３−（ジブチルアミノ）プロピルアミノ］−１，３，５−トリアジン−２−イルアミノ］アニリン等を反応させることによって得られる。
【００３４】
式（１１） −ＳＯ2Ｃｌ
式（１２） −ＣＯＣｌ
式（１３） −ＣＨ2ＮＨＣＯＣＨ2Ｃｌ
式（１４） −ＣＨ2Ｃｌ
また、有機色素がアゾ系色素である場合は、式（２）〜式（５）で示される置換基をあらかじめジアゾ成分またはカップリング成分に導入し、その後カップリング反応を行うことによってアゾ系顔料誘導体を製造することもできる。
【００３５】
本発明の塩基性基を有するトリアジン誘導体は、種々の合成経路で合成することができる。例えば、塩化シアヌルを出発原料とし、塩化シアヌルの少なくとも１つの塩素に式（２）〜式（５）で示される置換基を形成するアミン成分、例えば、Ｎ，Ｎ−ジメチルアミノプロピルアミンまたはＮ−メチルピペラジン等を反応させ、次いで塩化シアヌルの残りの塩素と種々のアミンまたはアルコール等を反応させることによって得られる。
【００３６】
本発明を構成する顔料は、ジケトピロロピロール系顔料、アゾ、ジスアゾ、ポリアゾ等のアゾ系顔料、銅フタロシアニン、ハロゲン化銅フタロシアニン、無金属フタロシアニン等のフタロシアニン系顔料、アミノアントラキノン、ジアミノジアントラキノン、アントラピリミジン、フラバントロン、アントアントロン、インダントロン、ピラントロン、ビオラントロン等のアントラキノン系顔料、キナクリドン系顔料、ジオキサジン系顔料、ペリノン系顔料、ペリレン系顔料、チオインジゴ系顔料、イソインドリン系顔料、イソインドリノン系顔料、キノフタロン系顔料、スレン系顔料、金属錯体系顔料等の有機顔料、または、酸化チタン、亜鉛華、硫化亜鉛、鉛白、炭酸カルシウム、沈降性硫酸バリウム、ホワイトカーボン、アルミナホワイト、カオリンクレー、タルク、ベントナイト、黒色酸化鉄、カドミウムレッド、べんがら、モリブデンレッド、モリブデートオレンジ、クロムバーミリオン、黄鉛、カドミウムイエロー、黄色酸化鉄、チタンイエロー、酸化クロム、ビリジアン、チタンコバルトグリーン、コバルトグリーン、コバルトクロムグリーン、ビクトリアグリーン、群青、紺青、コバルトブルー、セルリアンブルー、コバルトシリカブルー、コバルト亜鉛シリカブルー、マンガンバイオレット、コバルトバイオレット等の無機顔料、または、アセチレンブラック、チャンネルブラック、ファーネスブラック等のカーボンブラックである。
【００３７】
本発明の顔料組成物において、リン酸基を有するエチレン性不飽和単量体と式（１）で示されるエチレン性不飽和単量体とを共重合成分として含む共重合体の配合量は、顔料１００重量部に対し好ましくは０．１〜５０重量部である。また、塩基性基を有する顔料誘導体の配合量は、顔料１００重量部に対して、好ましくは１〜３０重量部、更に好ましくは５〜２０重量部である。
【００３８】
本発明の顔料組成物は、必要により各種溶剤、樹脂、添加剤、市販分散剤等と混合して、横型サンドミル、縦型サンドミル、アニュラー型ビーズミル、アトライター等で分散することにより、顔料組成物をワニスに分散せしめてなる顔料分散体を調製することができる。共重合体、塩基性基を有する顔料誘導体、塩基性基を有するアントラキノン誘導体または塩基性基を有するトリアジン誘導体（以下、塩基性基を有する顔料誘導体等という。）、顔料、その他の樹脂、添加剤は、すべての成分を混合してから分散してもよいが、初めに共重合体と塩基性基を有する顔料誘導体等と顔料のみ、あるいは、共重合体と塩基性基を有する顔料誘導体等のみを分散し、次いで、順次他の成分を添加して再度分散を行ってもよい。
【００３９】
また、横型サンドミル、縦型サンドミル、アニュラー型ビーズミル、アトライター等で分散を行う前に、ニーダー、３本ロールミル等の練肉混合機を使用した前分散、２本ロールミル等による固形分散、または顔料への共重合体と塩基性基を有する顔料誘導体等の処理を行ってもよい。また、ハイスピードミキサー、ホモミキサー、ボールミル、ロールミル、石臼式ミル、超音波分散機等のあらゆる分散機や混合機が本発明の分散体を製造するために利用できる。
本発明の顔料分散体に用いることができる各種溶剤としては、有機溶剤、水等が挙げられる。
【００４０】
また、本発明の顔料分散体に用いることができ樹脂の例としては、石油樹脂、カゼイン、セラック、ロジン変性マレイン酸樹脂、ロジン変性フェノール樹脂、ニトロセルロース、セルロースアセテートブチレート、環化ゴム、塩化ゴム、酸化ゴム、塩酸ゴム、フェノール樹脂、アルキド樹脂、ポリエステル樹脂、不飽和ポリエステル樹脂、アミノ樹脂、エポキシ樹脂、ビニル樹脂、塩化ビニル、塩化ビニル−酢酸ビニル共重合体、アクリル樹脂、メタクリル樹脂、ポリウレタン樹脂、シリコーン樹脂、フッ素樹脂、乾性油、合成乾性油、スチレン変性マレイン酸、ポリアミド樹脂、塩素化ポリプロピレン、ブチラール樹脂、塩化ビニリデン樹脂等が挙げられる。
【００４１】
本発明の顔料分散体は、市販の分散剤、各種添加剤を含有することができる。本発明の顔料分散体は、非水系または水系の塗料、グラビアインキ、オフセットインキ、インキジェットインキ、プラスチック着色等に利用できる。
本発明の共重合体がカルボキシル基を有する場合には、親水性有機溶剤を含んでいてもよい水を溶媒として共重合体中のカルボキシル基をトリエチルアミン、ジメチルアミノエタノール、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、メチルアミン、ジメチルアミン、トリエチルアミン、アンモニア等の有機アミンまたは水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム等の無機アルカリで中和することにより、水性インキ、水性塗料等のワニスとして使用することができる。
【００４２】
【実施例】
以下に、本発明に関わる共重合体、塩基性基を有する顔料誘導体等の製造例、および本発明の実施例を示す。以下の「部」とは「重量部」を、「％」とは「重量％」をそれぞれ表す。共重合体の分子量は、ＧＰＣ（ゲルパーミエーションクロマトグラフィ）により測定したポリスチレン換算の重量平均分子量である。
[共重合体製造例１］
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けてシクロヘキサノン９８１部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりメチルメタクリレート３０部、ｎ−ブチルメタクリレート１６５部、２−ヒドロキシエチルメタクリレート４５部、メタクリル酸６０部、アシッドホスホキシエチルメタクリレート１５部、ポリプロピレングリコールモノアクリレート（日本油脂製「ブレンマーＡＰ−５５０」、式（１）におけるｎ＝９）９０部、２，２’−アゾビスイソブチロニトリル１５部の混合溶液を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、固形分３０％、重量平均分子量２４０００の共重合体（１）を得た。
【００４３】
[共重合体製造例２]
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けてシクロヘキサノン９８１部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりメチルメタクリレート３０部、ｎ−ブチルメタクリレート１６５部、２−ヒドロキシエチルメタクリレート４５部、メタクリル酸６０部、アシッドホスホキシエチルメタクリレート１５部、ポリプロピレングリコールモノメタクリレート（日本油脂製「ブレンマーＰＰ−５００」、式（１）におけるｎ＝９）９０部、２，２’−アゾビスイソブチロニトリル１５部の混合溶液を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、固形分３０％、重量平均分子量２６０００の共重合体（２）を得た。
【００４４】
[共重合体製造例３]
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けてシクロヘキサノン９８１部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりメチルメタクリレート３０部、ｎ−ブチルメタクリレート１６５部、２−ヒドロキシエチルメタクリレート４５部、メタクリル酸６０部、アシッドホスホキシエチルメタクリレート１５部、メトキシポリエチレングリコールモノメタクリレート（日本油脂製「ブレンマーＰＭＥ−４００」、式（１）におけるｎ＝９）９０部、２，２’−アゾビスイソブチロニトリル１５部の混合溶液を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、固形分３０％、重量平均分子量３００００の共重合体（３）を得た。
【００４５】
[共重合体製造例４]（比較例）
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けてシクロヘキサノン７３５部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりメチルメタクリレート３０部、ｎ−ブチルメタクリレート１６５部、２−ヒドロキシエチルメタクリレート４５部、メタクリル酸６０部、２，２’−アゾビスイソブチロニトリル１５部の混合溶液を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、固形分３０％、重量平均分子量１９０００の共重合体（４）を得た。
【００４６】
[共重合体製造例５]（比較例）
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けてシクロヘキサノン９４５部を仕込み、８０℃に昇温し反応容器内を窒素置換した後、滴下管よりメチルメタクリレート３０部、ｎ−ブチルメタクリレート１６５部、２−ヒドロキシエチルメタクリレート４５部、メタクリル酸６０部、ポリプロピレングリコールモノメタクリレート（日本油脂製「ブレンマーＰＰ−５００」、式（１）におけるｎ＝９）９０部、２，２’−アゾビスイソブチロニトリル１５部の混合溶液を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、固形分３０％、重量平均分子量２３０００の共重合体（５）を得た。
【００４７】
［塩基性基を有する顔料誘導体等の製造例１］
色素成分である銅フタロシアニン５０部をクロロスルホン化した後、アミン成分であるＮ，Ｎ−ジメチルアミノプロピルアミン１４部と反応させて顔料誘導体（１）６２部を得た。
顔料誘導体（１）
【化２３】
【００４８】
［塩基性基を有する顔料誘導体等の製造例２］
色素成分である銅フタロシアニン５０部をクロロメチル化した後、アミン成分であるジブチルアミン４０部と反応させて顔料誘導体（２）９５部を得た。
顔料誘導体（２）
【化２４】
【００４９】
［塩基性基を有する顔料誘導体等の製造例３］
色素成分であるキナクリドン５０部をクロロアセトアミドメチル化した後、アミン成分であるＮ−メチルピペラジン４０部と反応させて顔料誘導体（３）１０３部を得た。
顔料誘導体（３）
【化２５】
［塩基性基を有する顔料誘導体等の製造例４］
色素成分としてジフェニルジケトピロロピロールを、アミン成分としてＮ−アミノプロピルモルホリンを使用し、製造例１と同様の方法により、顔料誘導体（４）を得た。
顔料誘導体（４）
【化２６】
［塩基性基を有する顔料誘導体等の製造例５］
アントラキノン−β−カルボン酸クロリド５０部と、アミン成分Ｎ，Ｎ−ジエチルアミノプロピルアミン３６部を反応させて、アントラキノン誘導体（５）６６部を得た。
アントラキノン誘導体（５）
【化２７】
［塩基性基を有する顔料誘導体等の製造例６］
色素成分としてジオキサジンバイオレット（Pigment Violet２３）を、アミン成分として式（１５）で示される化合物を使用し、製造例１と同様の方法により、顔料誘導体（６）を得た。
式（１５）
【化２８】
【化２９】
［塩基性基を有する顔料誘導体等の製造例７］
ジアゾ成分ｐ−ニトロアニリン５０部と、式（１６）で表されるアミン成分を有するカップラー１０９部をジアゾカップリング反応させることにより、顔料誘導体（７）１６０部を得た。
式（１６）
【化３０】
【化３１】
［塩基性基を有する顔料誘導体等の製造例８］
テトラゾ成分ジクロロベンジジン５０部と、式（１７）で表されるアミン成分を有するカップラー２１２部をジアゾカップリング反応させることにより、顔料誘導体（８）２６３部を得た。
式（１７）
【化３２】
【化３３】
［塩基性基を有する顔料誘導体等の製造例９］
アニリン５０部、塩化シアヌル９９部、Ｎ，Ｎ−ジメチルアミノプロピルアミン５５部をメタノール中で反応させることにより、トリアジン誘導体（９）１６８部を得た。
トリアジン誘導体（９）
【化３４】
製造例１〜９と同様の方法で、色素成分、アントラキノン、アクリドンまたはトリアジンと、アミン成分を反応することにより、または、アミン成分を有する化合物をカップリング反応して色素を合成することにより、本発明を構成する種々の顔料誘導体を製造することができる。
（分散体の製造と評価）
本発明の顔料分散体の性能を評価するために、表１および表２に示す組成の塗料を作成した。なお、シンナーとしては、シクロヘキサノン／キシレン／ｎ−ブタノール＝６／２／２（重量比）からなる混合溶剤を使用した。また、分散はスチールボールを使用し、ペイントシェイカーにて行った。得られた塗料の粘度をＢ型粘度計で測定し、粘度およびＴＩ値で分散体の性能を評価した（粘度は低いほど良好。ＴＩ値は１に近いほど良好。）。結果を表１および表２に示す。
本発明の分散体は、比較例に比べ、良好な粘度、ＴＩ値を示した。
【００５７】
【表１】
【発明の効果】
本発明の顔料組成物、特に有機顔料を含む顔料組成物を各種ビヒクルに分散することにより、塩基性基を有する顔料誘導体、塩基性基を有するアントラキノン誘導体、塩基性基を有するアクリドン誘導体または塩基性基を有するトリアジン誘導体と、共重合体との相乗効果で顔料分散性が飛躍的に改善され、安定な顔料分散体が得られる。
そのため、本発明の顔料組成物を使用すれば、ビヒクルに含まれる樹脂の顔料分散性が悪い場合でも、常に安定な顔料分散体を製造することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a pigment composition and a pigment dispersion which are excellent in suitability for use, in particular, non-aggregability and fluidity.
[0002]
[Prior art]
In general, when fine pigment particles are dispersed in vehicles such as offset inks, gravure inks and paints, it is difficult to obtain a stable dispersion, which causes various problems in manufacturing operations and the value of the resulting product. It has been known.
For example, dispersions containing pigments consisting of fine particles often exhibit high viscosity, making the product difficult to remove and transport from the disperser, and if worse, cause gelation during storage. It may be difficult to use. Furthermore, regarding the coating film surface of the color-exposed product, a state defect such as a decrease in gloss and a leveling defect may occur. In addition, when different types of pigments are used in combination, color unevenness due to aggregation or phenomena such as sedimentation may cause color unevenness or a significant reduction in coloring power.
[0003]
In order to solve the various problems as described above, a method in which an organic pigment is used as a base skeleton and a pigment derivative having an acidic group or a basic group as a substituent in the side chain is mixed as a dispersant is disclosed in JP-B-41-2466. No. 2, U.S. Pat. No. 2,855,403, JP-A-63-305173, JP-A-1-247468, JP-A-3-26767, and the like. In addition, use of inorganic materials is disclosed in JP-A-11-104479, JP-A-11-116238, and the like.
However, it is not effective for all materials, and particularly for organic pigments, a good dispersion cannot be obtained. In addition, since there are a large number of varnish systems in paints, inks, etc., even if these methods are used, a satisfactory effect is not obtained except for some varnish systems.
[0004]
[Problems to be solved by the invention]
Accordingly, an object of the present invention is to provide a stable pigment composition and pigment dispersion excellent in non-aggregation property and fluidity suitable for offset ink, gravure ink, paint, ink jet ink and the like.
[0005]
[Means for Solving the Problems]
The inventors of the present invention provide a copolymer containing a pigment derivative, anthraquinone derivative, acridone derivative or triazine derivative having a basic group, a monomer having a phosphate group and a monomer having an alkylene oxide chain as a copolymerization component. It has been found that the pigment dispersibility is drastically improved by using the coalescence together, and the present invention has been achieved.
That is, the present invention provides at least one selected from a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an acridone derivative having a basic group, or a triazine derivative having a basic group, and an ethylenic group having a phosphate group. The present invention relates to a pigment composition comprising a copolymer containing an unsaturated monomer and an ethylenically unsaturated monomer represented by the following formula (1) as a copolymerization component, and a pigment.
The present invention also relates to a pigment dispersion obtained by dispersing the pigment composition in a varnish.
[0006]
Formula (1)
[Chemical 8]
R 2 : Represents an alkylene group having 2 to 4 carbon atoms.
R Three : Hydrogen atom, alkyl group having 1 to 30 carbon atoms, -CH 2 -CH = CH 2 , An optionally substituted phenyl group or -C (= 0) -C (R 1 ) = CH 2 Represents.
n: represents an integer of 2 to 100.
[0007]
The copolymer containing the ethylenically unsaturated monomer having a phosphate group of the present invention and the ethylenically unsaturated monomer represented by the following formula (1) as a copolymerization component is an ethylenic group having a phosphate group. Copolymer obtained by radical polymerization of unsaturated monomer, ethylenically unsaturated monomer represented by formula (1), and, if necessary, ethylenically unsaturated monomer other than the monomer It is.
[0008]
The ethylenically unsaturated monomer having a phosphate group is a compound having a phosphate group and an ethylenically unsaturated double bond, and the phosphate group is a divalent phosphate group represented by the following formula (8). Even a monovalent phosphate group represented by the following formula (9) may be used. Phosphoric acid groups are metals such as sodium and potassium, or diethylamine, dibutylamine, triethanolamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, octylamine, dodecylamine, stearylamine, oleylamine, distearyl. A salt may be formed with an organic amine such as an amine.
[0009]
Formula (8)
[Chemical 9]
[Chemical Formula 10]
Examples of the ethylenically unsaturated monomer having a phosphoric acid group include the following general formula represented by ethylene glycol methacrylate phosphate, propylene glycol methacrylate phosphate, ethylene glycol acrylate phosphate, and propylene glycol acrylate phosphate. The compound shown by (10) is mentioned.
Formula (10)
Embedded image
R 14 : Represents an alkylene group.
l: represents an integer of 1 to 20.
[0011]
Specific examples of the ethylenically unsaturated monomer having a phosphate group are shown below, but are not limited thereto.
Embedded image
Embedded image
These ethylenically unsaturated monomers having a phosphoric acid group can be produced by the methods described in JP-B-50-22536, JP-A-58-128393, and the like. Commercially available products include Phosmer M, Phosmer CL, Phosmer PE, Phosmer MH (above, Unichemical Co., Ltd.), Light Ester P-1M (above, Kyoeisha Chemical Co., Ltd.), JAMP-514 (above, Johoku Chemical Industries, Ltd. ), KAYAMER PM-2, KAYAMER PM-21 (manufactured by Nippon Kayaku Co., Ltd.), and the like.
[0014]
These ethylenically unsaturated monomers having a phosphate group can be used alone or in combination of two or more. Moreover, the copolymerization ratio of the ethylenically unsaturated monomer having a phosphate group in the copolymer is 0.1 to 30 weights with respect to 100 parts by weight in total of all monomers constituting the copolymer. Parts, preferably 0.1 to 5 parts by weight.
[0015]
Of the ethylenically unsaturated monomers represented by the formula (1), R Three Examples of the hydroxyl-terminated polyalkylene glycol mono (meth) acrylate in which is a hydrogen atom include polyethylene glycol monomethacrylate, polyethylene glycol monoacrylate, polypropylene glycol monomethacrylate, polypropylene glycol monoacrylate, and poly (ethylene glycol-propylene glycol) monomethacrylate. , Polyethylene glycol-polypropylene glycol monomethacrylate, polyethylene glycol-polypropylene glycol monoacrylate, poly (ethylene glycol-tetramethylene glycol) monomethacrylate, poly (ethylene glycol-tetramethylene glycol) monoacrylate, poly (propylene glycol-tetramethylene glycol) Monometaacryl DOO, poly (propylene glycol - tetramethylene glycol) monoacrylate, propylene glycol polytetramethylene glycol monomethacrylate, propylene glycol polytetramethylene glycol monoacrylate.
[0016]
R Three Examples of the alkyl group-terminated polyalkylene glycol mono (meth) acrylate in which is an alkyl group having 1 to 30 carbon atoms include methoxypolyethylene glycol monomethacrylate, methoxypolyethyleneglycol monoacrylate, octoxypolyethyleneglycol monoacrylate, octoxypolyethyleneglycol Polypropylene glycol monomethacrylate, octoxy polyethylene glycol polypropylene glycol monoacrylate, lauroxy polyethylene glycol monoacrylate, lauroxy polyethylene glycol monoacrylate, stearoxy polyethylene glycol monomethacrylate, stearoxy polyethylene glycol-polypropylene glycol monoacrylate, and the like.
[0017]
R Three -CH 2 -CH = CH 2 Examples of the allyl group-terminated polyalkylene glycol mono (meth) acrylate include allyloxy polyethylene glycol-polypropylene glycol monomethacrylate, allyloxy polyethylene glycol-polypropylene glycol monoacrylate, and the like.
R Three Examples of the phenyl group-terminated polyalkylene glycol mono (meth) acrylate in which is a phenyl group which may have a substituent include nonyl phenoxy polyethylene glycol monoacrylate, nonyl phenoxy polyethylene glycol-polypropylene glycol monomethacrylate, and nonyl phenoxy. Polypropylene glycol-polyethylene glycol monomethacrylate, nonylphenoxy poly (ethylene glycol-propylene glycol) monoacrylate, phenol EO modified acrylate, nonylphenol EO modified acrylate, and the like.
[0018]
R Three -C (= 0) -C (R 1 ) = CH 2 Examples of polyalkylene glycol mono (meth) acrylates having both terminal (meth) acryloyl groups include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol dimethacrylate, polypropylene glycol Diacrylate, polytetramethylene glycol dimethacrylate, polytetramethylene glycol diacrylate, poly (ethylene glycol-tetramethylene glycol) dimethacrylate, poly (ethylene glycol-tetramethylene glycol) diacrylate, poly (propylene glycol-tetramethylene glycol) Dimethacrylate, poly (propylene glycol-tetra Methylene glycol) diacrylate, polyethylene glycol-polypropylene glycol-polyethylene glycol diacrylate, and the like.
[0019]
These monomers are commercially available from, for example, Nippon Oil & Fat Co., Ltd. as the Blemmer series and Toa Gosei Co., Ltd. as the Aronix series.
The ethylenically unsaturated monomer represented by the formula (1) can be used alone or in combination of two or more. Moreover, the copolymerization ratio of the ethylenically unsaturated monomer represented by the formula (1) in the copolymer is 0.1 to 100 parts by weight with respect to a total of 100 parts by weight of all the monomers constituting the copolymer. The amount is preferably 50 parts by weight.
[0020]
Examples of ethylenically unsaturated monomers having a phosphoric acid group or (other) ethylenically unsaturated monomers other than the ethylenically unsaturated monomer represented by the formula (1) include methyl acrylate and ethyl acrylate. , Butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, stearyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate (meta ) Acrylic acid alkyl esters, styrene, α-methylstyrene, vinyltoluene, vinyl acetate, vinyl propionate, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl ( (Meth) acrylate, -Hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, glycerin (meth) acrylate, polycaprolactone-modified hydroxyethyl (meth) acrylate (n = 1-6), epoxy (Meth) acrylate, hydroxyl-terminated urethane (meth) acrylate and the like can be mentioned.
[0021]
The other ethylenically unsaturated monomer may be an ethylenically unsaturated monomer having at least one carboxyl group in the molecule, such as acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, Examples include phthalic acid monohydroxyethyl acrylate, ω-carboxy-polycaprolactone monoacrylate, maleic acid, itaconic acid, fumaric acid, glutaconic acid, and tetrahydrophthalic acid. These can be used alone or in combination of two or more. In the case where an ethylenically unsaturated monomer having at least one carboxyl group in the molecule is included as a copolymerization component, the copolymerization ratio of the monomer is the same as that of all monomers constituting the copolymer. It is preferable that it is 1-50 weight part with respect to a total of 100 weight part.
[0022]
The weight average molecular weight (Mw) of the copolymer of the present invention is preferably 1000 to 100,000, more preferably 5000 to 30000, from the viewpoint of good dispersibility.
The copolymer of the present invention is synthesized in the presence of an initiator in an inert gas stream at 50 to 150 ° C. for 2 to 10 hours. If necessary, it may be performed in the presence of a solvent.
[0023]
Initiators include organic peroxides such as benzoyl peroxide, cumene hydroperoxide, t-butyl hydroperoxide, diisopropyl peroxycarbonate, di-t-butyl peroxide, t-butyl peroxybenzoate, 2,2 ′ -Azo compounds such as azobisisobutyronitrile. The initiator is preferably used in an amount of 1 to 20 parts by weight with respect to a total of 100 parts by weight of the ethylenically unsaturated monomer.
[0024]
As the solvent, water and / or a water-miscible organic solvent, or acetic acid esters such as ethyl cellosolve acetate and propylene glycol monomethyl ether acetate; ketones such as cyclohexanone and methyl isobutyl ketone; xylene, ethylbenzene and the like can be used. Examples of the water-miscible organic solvent include alcohol solvents such as ethyl alcohol, isopropyl alcohol and n-propyl alcohol, and mono- or dialkyl ethers of ethylene glycol or diethylene glycol.
[0025]
A pigment derivative having a basic group, an anthraquinone derivative having a basic group, an acridone derivative having a basic group, or a triazine derivative having a basic group constituting the present invention is represented by the following general formulas (2), (3), It has at least one substituent selected from the group represented by (4) and (5).
Formula (2)
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Formula (3)
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X: -SO 2 -, -CO-, -CH 2 NHCOCH 2 -, -CH 2 -Or represents a direct bond.
m represents an integer of 1 to 10.
R Four , R Five : Each independently an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or R Four And R Five Together represent an optionally substituted heterocycle containing further nitrogen, oxygen or sulfur atoms. As for carbon number of an alkyl group and an alkenyl group, 1-10 are preferable.
R 6 : Represents an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group. As for carbon number of an alkyl group and an alkenyl group, 1-10 are preferable.
R 7 , R 8 , R 9 , R Ten : Each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group. As for carbon number of an alkyl group and an alkenyl group, 1-5 are preferable.
[0028]
Y: -NR 11 -Z-NR 12 -Or represents a direct bond.
R 11 , R 12 : Each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group. As for carbon number of an alkyl group and an alkenyl group, 1-5 are preferable.
Z: represents an alkylene group that may be substituted, an alkenylene group that may be substituted, or a phenylene group that may be substituted. As for carbon number of an alkyl group and an alkenyl group, 1-8 are preferable.
P: The substituent shown by Formula (6) or the substituent shown by Formula (7) is represented.
Q: A hydroxyl group, an alkoxyl group, a substituent represented by the formula (6) or a substituent represented by the formula (7).
[0029]
Formula (6)
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Examples of the amine component used for forming the substituents represented by the formulas (2) to (7) include dimethylamine, diethylamine, N, N-ethylisopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, dibutylamine , Disec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N-methyloctadecylamine, didecylamine Diallylamine, N, -Ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamyl Amine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N-methyl-laurylaminopro Ruamine, N, N-ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecholine, 3-pipecholine, 4 -Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinmethanol, Pipecolic acid, Isonipecotic acid, Methyl isnicopetinate, Ethyl isonicopetic acid, 2-Piperidinethanol, Pyrrolidine, 3-hydroxy Pyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecoline, N-aminopropyl-4-pipecholine, N-aminopropyl Examples include propylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine and the like.
[0031]
Organic dyes constituting pigment derivatives having basic groups include, for example, diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine, flavantrons, anthanthrones , Indanthrone, pyranthrone, violanthrone, anthraquinone dyes, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes It is a dye such as a dye or a metal complex dye.
In addition, anthraquinone derivatives having a basic group and acridone derivatives having a basic group include alkyl groups such as methyl and ethyl groups, amino groups, nitro groups, hydroxyl groups or methoxy groups, alkoxy groups such as ethoxy groups, chlorine, etc. It may have a substituent such as halogen.
[0032]
Triazine derivatives having a basic group include alkyl groups such as methyl and ethyl groups, amino groups or dimethylamino groups, alkylamino groups such as diethylamino groups and dibutylamino groups, nitro groups, hydroxyl groups or methoxy groups, and ethoxy groups. , An alkoxy group such as a butoxy group, a halogen such as chlorine, or a phenyl group optionally substituted with a methyl group, a methoxy group, an amino group, a dimethylamino group, a hydroxyl group, or the like, or a methyl group, an ethyl group, a methoxy group, an ethoxy group 1,3,5-triazine which may have a substituent such as phenylamino group which may be substituted with a group, amino group, dimethylamino group, diethylamino group, nitro group, hydroxyl group and the like.
[0033]
The pigment derivative and anthraquinone derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, after introducing a substituent represented by formula (11) to formula (14) into an organic dye or anthraquinone, it reacts with the above substituent to form a substituent represented by formula (2) to formula (5). Amine components such as N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazine-2 Obtained by reacting -ylamino] aniline or the like.
[0034]
Formula (11) -SO 2 Cl
Formula (12) -COCl
Formula (13) -CH 2 NHCOCH 2 Cl
Formula (14) -CH 2 Cl
Further, when the organic dye is an azo dye, the substituent represented by the formula (2) to the formula (5) is introduced into the diazo component or the coupling component in advance, and then the coupling reaction is performed, thereby performing the azo pigment. Derivatives can also be produced.
[0035]
The triazine derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, starting from cyanuric chloride, an amine component that forms a substituent represented by formula (2) to formula (5) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N- It can be obtained by reacting methylpiperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.
[0036]
The pigment constituting the present invention includes diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, polyazo, phthalocyanine pigments such as copper phthalocyanine, halogenated copper phthalocyanine, and metal-free phthalocyanine, aminoanthraquinone, diaminodianthraquinone, Anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone and other anthraquinone pigments, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments Organic pigments such as pigments, quinophthalone pigments, selenium pigments, metal complex pigments, or titanium oxide, zinc white, zinc sulfide, white lead, calcium carbonate, precipitated barium sulfate, white carbon, alumina , Kaolin clay, talc, bentonite, black iron oxide, cadmium red, red pepper, molybdenum red, molybdate orange, chrome vermilion, chrome lead, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, viridian, titanium cobalt green , Cobalt green, cobalt chrome green, Victoria green, ultramarine, bitumen, cobalt blue, cerulean blue, cobalt silica blue, cobalt zinc silica blue, manganese violet, cobalt violet and other inorganic pigments, or acetylene black, channel black, furnace black Carbon black.
[0037]
In the pigment composition of the present invention, the blending amount of the copolymer containing an ethylenically unsaturated monomer having a phosphate group and the ethylenically unsaturated monomer represented by the formula (1) as a copolymerization component is as follows: Preferably it is 0.1-50 weight part with respect to 100 weight part of pigments. Moreover, the compounding quantity of the pigment derivative which has a basic group becomes like this. Preferably it is 1-30 weight part with respect to 100 weight part of pigments, More preferably, it is 5-20 weight part.
[0038]
The pigment composition of the present invention is mixed with various solvents, resins, additives, commercially available dispersants, etc., if necessary, and dispersed in a horizontal sand mill, vertical sand mill, annular bead mill, attritor, etc. It is possible to prepare a pigment dispersion obtained by dispersing in a varnish. Copolymers, pigment derivatives having basic groups, anthraquinone derivatives having basic groups or triazine derivatives having basic groups (hereinafter referred to as pigment derivatives having basic groups), pigments, other resins, additives May be dispersed after mixing all components, but only the pigment derivative having a copolymer and a basic group and the pigment, or only the pigment derivative having a copolymer and a basic group, etc. May be dispersed, and then another component may be sequentially added and dispersed again.
[0039]
Also, before dispersing with a horizontal sand mill, vertical sand mill, annular bead mill, attritor, etc., pre-dispersion using a kneader mixer such as a kneader, three-roll mill, etc., solid dispersion with a two-roll mill, etc., or pigment You may perform the process of the pigment derivative etc. which have a copolymer and a basic group. In addition, any disperser or mixer such as a high speed mixer, a homomixer, a ball mill, a roll mill, a stone mill, or an ultrasonic disperser can be used for producing the dispersion of the present invention.
Examples of various solvents that can be used in the pigment dispersion of the present invention include organic solvents and water.
[0040]
Examples of resins that can be used in the pigment dispersion of the present invention include petroleum resin, casein, shellac, rosin-modified maleic resin, rosin-modified phenol resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, Rubber, oxidized rubber, hydrochloric acid rubber, phenol resin, alkyd resin, polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacrylic resin, polyurethane Resins, silicone resins, fluororesins, drying oils, synthetic drying oils, styrene-modified maleic acid, polyamide resins, chlorinated polypropylene, butyral resins, vinylidene chloride resins, and the like.
[0041]
The pigment dispersion of the present invention can contain a commercially available dispersant and various additives. The pigment dispersion of the present invention can be used for non-aqueous or aqueous paints, gravure inks, offset inks, ink jet inks, plastic coloring, and the like.
When the copolymer of the present invention has a carboxyl group, the carboxyl group in the copolymer may be triethylamine, dimethylaminoethanol, monoethanolamine, diethanolamine, triethanol with water that may contain a hydrophilic organic solvent as a solvent. Use as a varnish for water-based inks, water-based paints, etc. by neutralizing with organic amines such as ethanolamine, methylamine, dimethylamine, triethylamine, ammonia, or inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate. Can do.
[0042]
【Example】
Examples of production of copolymers, pigment derivatives having a basic group and the like according to the present invention and examples of the present invention are shown below. In the following, “part” means “part by weight”, and “%” means “% by weight”. The molecular weight of the copolymer is a polystyrene-equivalent weight average molecular weight measured by GPC (gel permeation chromatography).
[Copolymer Production Example 1]
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer, charged with 981 parts of cyclohexanone, heated to 80 ° C. and purged with nitrogen, and then 30 parts of methyl methacrylate from the dropping tube. 165 parts of n-butyl methacrylate, 45 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, 15 parts of acid phosphoxyethyl methacrylate, polypropylene glycol monoacrylate (“Blemmer AP-550” manufactured by NOF Corporation, n = in formula (1) 9) A mixed solution of 90 parts and 15 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer (1) having a solid content of 30% and a weight average molecular weight of 24,000.
[0043]
[Copolymer production example 2]
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer, charged with 981 parts of cyclohexanone, heated to 80 ° C., and purged with nitrogen in the reaction vessel. 165 parts of n-butyl methacrylate, 45 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, 15 parts of acid phosphoxyethyl methacrylate, polypropylene glycol monomethacrylate (“Blemmer PP-500” manufactured by NOF Corporation, n = in formula (1) 9) A mixed solution of 90 parts and 15 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer (2) having a solid content of 30% and a weight average molecular weight of 26000.
[0044]
[Copolymer Production Example 3]
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer, charged with 981 parts of cyclohexanone, heated to 80 ° C. and purged with nitrogen, and then 30 parts of methyl methacrylate from the dropping tube. 165 parts of n-butyl methacrylate, 45 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, 15 parts of acid phosphoxyethyl methacrylate, methoxypolyethylene glycol monomethacrylate (“Blemmer PME-400” manufactured by NOF Corporation, n in formula (1) = 9) A mixed solution of 90 parts and 2,2'-azobisisobutyronitrile (15 parts) was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer (3) having a solid content of 30% and a weight average molecular weight of 30000.
[0045]
[Copolymer Production Example 4] (Comparative Example)
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirrer and charged with 735 parts of cyclohexanone. After raising the temperature to 80 ° C. and purging the inside of the reaction vessel with nitrogen, 30 parts of methyl methacrylate from the dropping tube, A mixed solution of 165 parts of n-butyl methacrylate, 45 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, and 15 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer (4) having a solid content of 30% and a weight average molecular weight of 19000.
[0046]
[Copolymer Production Example 5] (Comparative Example)
A separable four-necked flask was equipped with a thermometer, a condenser tube, a nitrogen gas inlet tube, and a stirring device, charged with 945 parts of cyclohexanone, heated to 80 ° C. and purged with nitrogen in the reaction vessel. 165 parts of n-butyl methacrylate, 45 parts of 2-hydroxyethyl methacrylate, 60 parts of methacrylic acid, 90 parts of polypropylene glycol monomethacrylate (“Blenmer PP-500” manufactured by NOF Corporation, n = 9 in formula (1)), 2, 2 A mixed solution of 15 parts of '-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was continued for 3 hours to obtain a copolymer (5) having a solid content of 30% and a weight average molecular weight of 23,000.
[0047]
[Production Example 1 of pigment derivative having basic group]
After 50 parts of copper phthalocyanine as a pigment component was chlorosulfonated, it was reacted with 14 parts of N, N-dimethylaminopropylamine as an amine component to obtain 62 parts of pigment derivative (1).
Pigment derivative (1)
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[0048]
[Production Example 2 of Pigment Derivative Having Basic Group, etc.]
After chloromethylating 50 parts of copper phthalocyanine as a pigment component, it was reacted with 40 parts of dibutylamine as an amine component to obtain 95 parts of pigment derivative (2).
Pigment derivative (2)
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[0049]
[Production Example 3 of Pigment Derivative Having Basic Group, etc.]
After 50 parts of quinacridone as a pigment component were chloroacetamidomethylated, it was reacted with 40 parts of N-methylpiperazine as an amine component to obtain 103 parts of pigment derivative (3).
Pigment derivative (3)
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[Production Example 4 of Pigment Derivative Having Basic Group, etc.]
A pigment derivative (4) was obtained in the same manner as in Production Example 1, using diphenyl diketopyrrolopyrrole as the dye component and N-aminopropylmorpholine as the amine component.
Pigment derivative (4)
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[Production Example 5 of pigment derivative having a basic group]
50 parts of anthraquinone-β-carboxylic acid chloride was reacted with 36 parts of the amine component N, N-diethylaminopropylamine to obtain 66 parts of an anthraquinone derivative (5).
Anthraquinone derivative (5)
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[Production Example 6 of Pigment Derivative Having Basic Group]
Pigment derivative (6) was obtained by the same method as in Production Example 1 using dioxazine violet (Pigment Violet 23) as the dye component and the compound represented by formula (15) as the amine component.
Formula (15)
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[Production Example 7 of Pigment Derivative Having Basic Group, etc.]
A diazo coupling reaction of 50 parts of diazo component p-nitroaniline and 109 parts of a coupler having an amine component represented by formula (16) gave 160 parts of pigment derivative (7).
Formula (16)
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[Production Example 8 of Pigment Derivative Having Basic Group]
The pigment derivative (8) 263 parts was obtained by carrying out a diazo coupling reaction of the tetrazo component dichlorobenzidine 50 parts and the coupler 212 part which has an amine component represented by Formula (17).
Formula (17)
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[Production Example 9 for Pigment Derivatives Having a Basic Group]
By reacting 50 parts of aniline, 99 parts of cyanuric chloride and 55 parts of N, N-dimethylaminopropylamine in methanol, 168 parts of a triazine derivative (9) was obtained.
Triazine derivative (9)
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By reacting the dye component, anthraquinone, acridone or triazine with an amine component in the same manner as in Production Examples 1 to 9, or by synthesizing a dye by coupling a compound having an amine component, Various pigment derivatives constituting the invention can be produced.
(Manufacture and evaluation of dispersion)
In order to evaluate the performance of the pigment dispersion of the present invention, paints having the compositions shown in Tables 1 and 2 were prepared. As a thinner, a mixed solvent consisting of cyclohexanone / xylene / n-butanol = 6/2/2 (weight ratio) was used. Dispersion was performed with a paint shaker using steel balls. The viscosity of the obtained paint was measured with a B-type viscometer, and the performance of the dispersion was evaluated based on the viscosity and TI value (the lower the viscosity, the better the TI value closer to 1). The results are shown in Tables 1 and 2.
The dispersion of the present invention showed better viscosity and TI value than the comparative example.
[0057]
[Table 1]
【The invention's effect】
By dispersing the pigment composition of the present invention, particularly a pigment composition containing an organic pigment, in various vehicles, a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an acridone derivative having a basic group, or a basic group The pigment dispersibility is drastically improved by a synergistic effect of the triazine derivative having a group and the copolymer, and a stable pigment dispersion is obtained.
Therefore, by using the pigment composition of the present invention, a stable pigment dispersion can always be produced even when the pigment dispersibility of the resin contained in the vehicle is poor.
Claims (4)
式（１）
Ｒ2 : 炭素数２〜４のアルキレン基を表す。
Ｒ3 : 水素原子、炭素数１〜３０のアルキル基、-CH2-CH=CH2 、置換基を有していてもよいフェニル基または-C(=0)-C(R1)=CH2 を表す。
ｎ : ２〜１００の整数を表す。An ethylenically unsaturated monomer having a phosphate group, at least one selected from a pigment derivative having a basic group, an anthraquinone derivative having a basic group, an acridone derivative having a basic group, or a triazine derivative having a basic group; A pigment composition comprising a copolymer containing an ethylenically unsaturated monomer represented by the following formula (1) as a copolymerization component, and a pigment.
Formula (1)
R 2 represents an alkylene group having 2 to 4 carbon atoms.
R 3 : a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, —CH 2 —CH═CH 2 , an optionally substituted phenyl group, or —C (= 0) —C (R 1 ) ═CH Represents 2 .
n: represents an integer of 2 to 100.
式（２）
m：１〜１０の整数を表す。
Ｒ4 、Ｒ5 ：それぞれ独立に、置換されていてもよいアルキル基、置換されていてもよいアルケニル基、置換されていてもよいフェニル基、またはＲ4 とＲ5 とで一体となって更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を表す。
Ｒ6 ：置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。
Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10：それぞれ独立に、水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。
Ｙ：−ＮＲ11−Ｚ−ＮＲ12−または直接結合を表す。
Ｒ11、Ｒ12：それぞれ独立に水素原子、置換されていてもよいアルキル基、置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。
Ｚ：置換されていてもよいアルキレン基、置換されていてもよいアルケニレン基、または置換されていてもよいフェニレン基を表す。
Ｐ：式（６）で示される置換基または式（７）で示される置換基を表す。
Ｑ：水酸基、アルコキシル基、式（６）で示される置換基または式（７）で示される置換基を表す。
式（６）
Formula (2)
m represents an integer of 1 to 10.
R 4 and R 5 : each independently an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted phenyl group, or a combination of R 4 and R 5 Represents an optionally substituted heterocycle containing a nitrogen, oxygen or sulfur atom.
R 6 : represents an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group.
R 7 , R 8 , R 9 , R 10 : each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group.
Y: represents —NR 11 —Z—NR 12 — or a direct bond.
R 11 and R 12 each independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group or an optionally substituted phenyl group.
Z: represents an optionally substituted alkylene group, an optionally substituted alkenylene group, or an optionally substituted phenylene group.
P: The substituent shown by Formula (6) or the substituent shown by Formula (7) is represented.
Q: A hydroxyl group, an alkoxyl group, a substituent represented by the formula (6) or a substituent represented by the formula (7).
Formula (6)
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| JP2007070567A (en) * | 2005-09-09 | 2007-03-22 | Dainippon Ink & Chem Inc | Aqueous pigment dispersion and water-based ink for inkjet recording |
| JP4678316B2 (en) * | 2006-02-28 | 2011-04-27 | 東洋インキ製造株式会社 | Pigment composition, pigment dispersion and ink |
| US9908991B2 (en) * | 2012-06-08 | 2018-03-06 | Dic Corporation | Organic pigment composition for color filters, method for producing the same, and color filter |
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