JP2011195694A - Yellow pigment dispersion - Google Patents
Yellow pigment dispersion Download PDFInfo
- Publication number
- JP2011195694A JP2011195694A JP2010063418A JP2010063418A JP2011195694A JP 2011195694 A JP2011195694 A JP 2011195694A JP 2010063418 A JP2010063418 A JP 2010063418A JP 2010063418 A JP2010063418 A JP 2010063418A JP 2011195694 A JP2011195694 A JP 2011195694A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- yellow
- acrylate
- meth
- viscosity
- 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
- 239000006185 dispersion Substances 0.000 title claims abstract description 36
- 239000001052 yellow pigment Substances 0.000 title claims abstract description 28
- 239000000049 pigment Substances 0.000 claims abstract description 62
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 230000002378 acidificating effect Effects 0.000 claims abstract description 13
- 239000002270 dispersing agent Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical group C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 239000000976 ink Substances 0.000 description 18
- 239000003999 initiator Substances 0.000 description 13
- -1 2-phenoxyethyl Chemical group 0.000 description 10
- 230000036962 time dependent Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 229910017053 inorganic salt Inorganic materials 0.000 description 5
- 239000012860 organic pigment Substances 0.000 description 5
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000003021 water soluble solvent Substances 0.000 description 4
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PRBBFHSSJFGXJS-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) prop-2-enoate;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O.C=CC(=O)OCC(C)(C)COC(=O)C=C PRBBFHSSJFGXJS-UHFFFAOYSA-N 0.000 description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OVJHMJJVXOJMBB-UHFFFAOYSA-N 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl)ethyl prop-2-enoate Chemical compound C1CCCC2C(=O)N(CCOC(=O)C=C)C(=O)C21 OVJHMJJVXOJMBB-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- DBHQYYNDKZDVTN-UHFFFAOYSA-N [4-(4-methylphenyl)sulfanylphenyl]-phenylmethanone Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 DBHQYYNDKZDVTN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ICCCRCJXHNMZPJ-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) 2,2-dimethyl-3-prop-2-enoyloxypropanoate Chemical compound C=CC(=O)OCC(C)(C)COC(=O)C(C)(C)COC(=O)C=C ICCCRCJXHNMZPJ-UHFFFAOYSA-N 0.000 description 1
- MXBCLXAAEYWALK-UHFFFAOYSA-N (2,2-dimethyl-3-prop-2-enoyloxypropyl) benzoate Chemical compound C=CC(=O)OCC(C)(C)COC(=O)C1=CC=CC=C1 MXBCLXAAEYWALK-UHFFFAOYSA-N 0.000 description 1
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- MJQHDSIEDGPFAM-UHFFFAOYSA-N (3-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(=O)C1=CC=CC=C1 MJQHDSIEDGPFAM-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- HMIBQFXWSUBFTG-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]ethanone Chemical compound CCN(CC)C1=CC=C(C(C)=O)C=C1 HMIBQFXWSUBFTG-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- CZZVAVMGKRNEAT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)CO.OCC(C)(C)C(O)=O CZZVAVMGKRNEAT-UHFFFAOYSA-N 0.000 description 1
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- NCHBYORVPVDWBJ-UHFFFAOYSA-N 2-(3-methylbutoxy)ethanol Chemical compound CC(C)CCOCCO NCHBYORVPVDWBJ-UHFFFAOYSA-N 0.000 description 1
- INFFATMFXZFLAO-UHFFFAOYSA-N 2-(methoxymethoxy)ethanol Chemical compound COCOCCO INFFATMFXZFLAO-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-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
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- FBEMBDJJVJHRHZ-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate;phthalic acid Chemical compound OCCOC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O FBEMBDJJVJHRHZ-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- MPAGVACEWQNVQO-UHFFFAOYSA-N 3-acetyloxybutyl acetate Chemical compound CC(=O)OC(C)CCOC(C)=O MPAGVACEWQNVQO-UHFFFAOYSA-N 0.000 description 1
- ZEHOVWPIGREOPO-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-[2-(4,5,6,7-tetrachloro-1,3-dioxoinden-2-yl)quinolin-8-yl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C(=O)N1C(C1=N2)=CC=CC1=CC=C2C1C(=O)C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2C1=O ZEHOVWPIGREOPO-UHFFFAOYSA-N 0.000 description 1
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- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- OFSAUHSCHWRZKM-UHFFFAOYSA-N Padimate A Chemical compound CC(C)CCOC(=O)C1=CC=C(N(C)C)C=C1 OFSAUHSCHWRZKM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- SEEVRZDUPHZSOX-UHFFFAOYSA-N [1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(C)=NOC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 238000006356 dehydrogenation reaction Methods 0.000 description 1
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- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 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
- 230000000694 effects Effects 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
本発明は、Ｃ.Ｉ.ピグメントイエロー１５０を含むイエロー顔料分散体であって、粘度の経時安定性が優れたものである。 The present invention is a yellow pigment dispersion containing CI Pigment Yellow 150, which has excellent viscosity stability over time.
本発明で使用しているＣ．Ｉ．ピグメントイエロー１５０は、耐候性が非常に高いイエロー顔料として知られており、屋外サイン用途など耐候性が必要な場面での需要が期待される。一方で、顔料の分散が非常に困難であり、例えば特許文献１では分散剤を２種類使用することで解決しているが、より少ない材料で安定な分散が可能な組合せが求められる。 C. used in the present invention. I. Pigment Yellow 150 is known as a yellow pigment having very high weather resistance, and is expected to be used in scenes that require weather resistance such as outdoor sign use. On the other hand, it is very difficult to disperse the pigment. For example, Patent Document 1 solves this problem by using two types of dispersants. However, a combination capable of stable dispersion with fewer materials is required.
従来インクジェット印刷に使用されるインキ組成物としては、溶剤型、水型、油性型など多岐にわたっているが、プラスチックやガラスなどの非吸収性の基材にも適用できること、溶剤の揮発量を低減させ環境に優しいことなどから、近年は活性エネルギー線硬化型インキの需要が増加している。とくに工業用インクジェット印刷においては、上記に加え耐水性、インキの乾燥エネルギー、乾燥によるヘッドへのインキ成分の付着などの点もあり、溶剤型や水型から活性エネルギー線硬化型インキへの置き換えが期待されている。 Conventional ink compositions used for inkjet printing are diverse, including solvent-type, water-type, and oil-type, but can also be applied to non-absorbable substrates such as plastic and glass, and reduce the amount of solvent volatilization. In recent years, demand for active energy ray curable ink has increased due to its environmental friendliness. Especially in industrial inkjet printing, in addition to the above, there are also water resistance, ink drying energy, adhesion of ink components to the head by drying, etc., so it is possible to replace solvent type or water type with active energy ray curable ink. Expected.
特許文献２、３では、Ｃ．Ｉ．ピグメントイエロー１５０の分散を実施しているが、本発明のように、僅か１種類の活性エネルギー線硬化型モノマーで分散を実施するには至っていない。顔料分散する上で、構成要素数が少ないほど相互作用の可能性が薄まるため、保存安定性が優れる傾向にあるが、特許文献２、３では顔料分散体自体の保存安定性については触れられていない。また、特許文献４では、本発明と異なるタイプの顔料分散剤を使用し、かつ顔料誘導体を使用してＣ．Ｉ．ピグメントイエロー１５０の分散を実施しているが、カラーフィルター用途であるため分散媒は一般的な溶剤である。活性エネルギー線硬化型インキは、溶剤を活性エネルギー線硬化型モノマーに単純に変更するだけでは完成されず、適正分散剤の選択、適正モノマーの選択、顔料分散体の保存安定性実現などの課題が蓄積していた。 In Patent Documents 2 and 3, C.I. I. Although pigment yellow 150 is dispersed, it has not yet been achieved with only one kind of active energy ray-curable monomer as in the present invention. When the pigment is dispersed, the smaller the number of constituent elements, the smaller the possibility of interaction. Therefore, the storage stability tends to be excellent. However, Patent Documents 2 and 3 mention the storage stability of the pigment dispersion itself. Absent. In Patent Document 4, a pigment dispersant different from the present invention is used, and a pigment derivative is used to obtain C.I. I. Pigment Yellow 150 is dispersed, but the dispersion medium is a general solvent because it is used for color filters. Active energy ray curable ink cannot be completed simply by changing the solvent to an active energy ray curable monomer, but there are issues such as selection of the proper dispersant, selection of the proper monomer, and storage stability of the pigment dispersion. Accumulated.
本発明は、Ｃ.Ｉ.ピグメントイエロー１５０を含むイエロー顔料分散体であって、粘度の経時安定性が優れたものを提供することを目的とする。 An object of the present invention is to provide a yellow pigment dispersion containing CI Pigment Yellow 150 and having excellent viscosity stability over time.
本発明の上記目的は、以下の構成により達成される。
本発明のイエロー顔料分散体は（Ａ）イエロー顔料、（Ｂ）顔料分散剤、（Ｃ）活性エネルギー線硬化型モノマーを含み、前記（Ａ）イエロー顔料は、Ｃ.Ｉ.ピグメントイエロー１５０であり、（Ｂ）顔料分散剤は櫛型骨格をもつ塩基性の高分子分散剤であり、（Ｃ）活性エネルギー線硬化型モノマーは、分子内に芳香環をもつことを特徴とする。
The above object of the present invention is achieved by the following configurations.
The yellow pigment dispersion of the present invention contains (A) a yellow pigment, (B) a pigment dispersant, and (C) an active energy ray-curable monomer, and the (A) yellow pigment is CI Pigment Yellow 150. (B) The pigment dispersant is a basic polymer dispersant having a comb skeleton, and (C) the active energy ray-curable monomer has an aromatic ring in the molecule.
更に、本発明は顔料と異なる構造をもつ酸性顔料誘導体を含むことを特徴とする、イエロー顔料分散体に関する。 Furthermore, this invention relates to the yellow pigment dispersion characterized by including the acidic pigment derivative which has a structure different from a pigment.
更に、本発明は、前記酸性顔料分散体がジスアゾ骨格、又はキノフタロン骨格をもつ酸性顔料分散体であることを特徴とする、イエロー顔料分散体に関する。 Furthermore, the present invention relates to a yellow pigment dispersion, wherein the acidic pigment dispersion is an acidic pigment dispersion having a disazo skeleton or a quinophthalone skeleton.
更に、本発明は、上記のイエロー顔料を含むことを特徴とする、活性エネルギー線硬化型インクジェットインキに関する。 Furthermore, the present invention relates to an active energy ray-curable ink-jet ink comprising the above yellow pigment.
本発明により、粘度の経時安定性に優れたイエロー顔料分散体を提供することができた。 According to the present invention, it was possible to provide a yellow pigment dispersion having excellent viscosity stability over time.
本発明で使用するイエロー顔料であるＣ．Ｉ．ピグメントイエロー１５０はモノアゾ骨格をもつニッケル錯体であり、ランクセス社の「Ｙｅｌｌｏｗ Ｐｉｇｍｅｎｔ Ｅ４ＧＮ」、「Ｙｅｌｌｏｗ Ｐｉｇｍｅｎｔ Ｅ４ＧＮ−ＧＴ」、ＢＡＳＦ社の「Ｃｉｂａ ＣＲＯＭＯＰＨＴＡＬ Ｙｅｌｌｏｗ ＬＡ２」などとして市販されている。 C.I. which is a yellow pigment used in the present invention. I. Pigment Yellow 150 is a nickel complex having a monoazo skeleton, and is commercially available as “Yellow Pigment E4GN”, “Yellow Pigment E4GN-GT” from LANXESS, “Ciba CROMOPHTAL Yellow LA2” from BASF, and the like.
更に、Ｃ．Ｉ．ピグメントイエロー１５０は、優れた耐候性をもつ特徴がある。 Furthermore, C.I. I. Pigment Yellow 150 is characterized by excellent weather resistance.
本発明で使用するＣ．Ｉ．ピグメントイエロー１５０は、一次粒径７０〜１５０ｎｍが好ましく、８０〜１２０ｎｍがより好ましい。更に単位質量あたりの表面積から算出される比表面積は６０〜１００ｃｍ２/ｇが好ましく、７０〜９０ｃｍ２/ｇがより好ましい。
有機顔料の微細化は下記の方法で行うことができる。すなわち、有機顔料、有機顔料の３重量倍以上の水溶性の無機塩および水溶性の溶剤の少なくとも３つの成分からなる混合物を粘土状の混合物とし、ニーダー等で強く練りこんで微細化したのち水中に投入し、ハイスピードミキサー等で攪拌してスラリー状とする。次いで、スラリーの濾過と水洗を繰り返して、水溶性の無機塩および水溶性の溶剤を除去する。微細化工程において、樹脂、顔料分散剤等を添加してもよい。
水溶性の無機塩としては、塩化ナトリウム、塩化カリウム等が挙げられる。これらの無機塩は、有機顔料の３重量倍以上、好ましくは２０重量倍以下の範囲で用いる。無機塩の量が３重量倍よりも少ないと、所望の大きさの処理顔料が得られない。また、２０重量倍よりも多いと、後の工程における洗浄処理が多大であり、有機顔料の実質的な処理量が少なくなる。
C. used in the present invention I. Pigment Yellow 150 preferably has a primary particle size of 70 to 150 nm, more preferably 80 to 120 nm. The specific surface area is further calculated from the surface area per unit mass is preferably 60~100cm 2 / g, 70~90cm 2 / g is more preferable.
The organic pigment can be refined by the following method. That is, a mixture comprising at least three components of an organic pigment, a water-soluble inorganic salt that is at least 3 times the weight of the organic pigment, and a water-soluble solvent is made into a clay-like mixture, and is kneaded strongly with a kneader or the like and then refined. And stirred with a high speed mixer or the like to form a slurry. Next, filtration and washing of the slurry are repeated to remove the water-soluble inorganic salt and the water-soluble solvent. In the miniaturization step, a resin, a pigment dispersant and the like may be added.
Examples of the water-soluble inorganic salt include sodium chloride and potassium chloride. These inorganic salts are used in the range of 3 times by weight or more, preferably 20 times by weight or less of the organic pigment. When the amount of the inorganic salt is less than 3 times by weight, a treated pigment having a desired size cannot be obtained. On the other hand, if the amount is more than 20 times by weight, the washing process in the subsequent step is great, and the substantial amount of the organic pigment is reduced.
水溶性の溶剤は、有機顔料と破砕助剤として用いられる水溶性の無機塩との適度な粘土状態をつくり、充分な破砕を効率よく行うために用いられ、水に溶解する溶剤であれば特に限定されないが、混練時に温度が上昇して溶剤が蒸発し易い状態になるため、安全性の点から沸点１２０〜２５０℃の高沸点の溶剤が好ましい。水溶性溶剤としては、２−（メトキシメトキシ）エタノール、２−ブトキシエタノール、２−（イソペンチルオキシ）エタノール、２−（ヘキシルオキシ）エタノール、ジエチレングリコール、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコール、トリエチレングリコールモノメチルエーテル、液体ポリエチレングリコール、１−メトキシ−２−プロパノール、１−エトキシ−２−プロパノール、ジプロピレングリコール、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、低分子量ポリプロピレングリコール等が挙げられる。 The water-soluble solvent is an organic solvent and a water-soluble inorganic salt that is used as a crushing aid, and is used for efficient crushing efficiently, especially if it is a solvent that dissolves in water. Although not limited, a high boiling point solvent having a boiling point of 120 to 250 ° C. is preferable from the viewpoint of safety because the temperature rises during kneading and the solvent is easily evaporated. Examples of water-soluble solvents include 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether , Triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, low molecular weight Examples thereof include polypropylene glycol.
本発明の顔料分散体に含まれるイエロー顔料は、インキ化後の耐候性の保持、発色などから、顔料分散体に対して１０〜３０％含有されるのが望ましい。
本発明の櫛型骨格をもつ塩基性顔料分散剤として用いられるグラフト型高分子化合物については、特に制限されないが、特開昭５４−３７０８２号公報、特開昭６１−１７４９３９号公報などに記載のポリアルキレンイミンとポリエステル化合物を反応させた化合物、特開平９−１６９８２１号公報に記載のポリアリルアミンの側鎖のアミノ基をポリエステルで修飾した化合物、特開昭６０−１６６３１８号公報に記載のポリエステルポリオール付加ポリウレタン等が挙げられ、更に、特開平９−１７１２５３号公報や、マクロモノマーの化学と工業（アイピーシー出版部、１９８９年）などにあるように、重合性オリゴマー（以下、マクロモノマーと称する）を共重合成分とするグラフト型高分子化合物も挙げることができる。
本発明の櫛型骨格をもつ塩基性顔料分散剤は、日本ルーブリゾール社よりソルスパース１３０００シリーズ、２４０００ＳＣ、２４０００ＧＲ、２８０００、３２０００シリーズ、３３０００、３５０００シリーズ、３６０００シリーズ、３９０００の商品名で市販されているのでこれを利用してもよく、このうちソルスパース３２０００を用いることがより好ましい。
The yellow pigment contained in the pigment dispersion of the present invention is desirably contained in an amount of 10 to 30% with respect to the pigment dispersion from the viewpoint of maintaining weather resistance after ink formation and color development.
The graft polymer compound used as a basic pigment dispersant having a comb-shaped skeleton according to the present invention is not particularly limited, but is described in JP-A Nos. 54-37082 and 61-174939. A compound obtained by reacting a polyalkyleneimine and a polyester compound, a compound in which the amino group of the side chain of polyallylamine described in JP-A-9-169821 is modified with polyester, a polyester polyol described in JP-A-60-166318 Additive polyurethanes and the like, and further, polymerizable oligomers (hereinafter referred to as macromonomers) as disclosed in JP-A-9-171253 and macromonomer chemistry and industry (IPC Publishing Department, 1989). There may also be mentioned graft-type polymer compounds having a copolymer component.
The basic pigment dispersant having a comb-shaped skeleton of the present invention is commercially available from Nippon Lubrizol under the trade names of Solsperse 13000 series, 24000SC, 24000GR, 28000, 32000 series, 33000, 35000 series, 36000 series, 39000. Therefore, this may be used, and among these, Solsperse 32000 is more preferably used.
本発明の芳香環をもつ活性エネルギー硬化型モノマーとしては、ベンジルアクリレート、フェノキシエチルアクリレート、フェノキシポリエチレングリコールアクリレート、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、ノニルフェノールＰＯ変性アクリレート、ビスフェノールＡ ＥＯ変性ジアクリレート、ビスフェノールＦ ＥＯ変性ジアクリレート、２−ヒドロキシ−３−フェノキシプロピルアクリレート、フタル酸モノヒドロキシエチルアクリレート、ネオペンチルグリコールアクリル酸安息香酸エステルなどが挙げられるが、これらに限定されるものではない。 Examples of the active energy curable monomer having an aromatic ring of the present invention include benzyl acrylate, phenoxyethyl acrylate, phenoxy polyethylene glycol acrylate, phenol EO modified acrylate, nonylphenol EO modified acrylate, nonylphenol PO modified acrylate, bisphenol A EO modified diacrylate, bisphenol. Examples include, but are not limited to, FE-modified diacrylate, 2-hydroxy-3-phenoxypropyl acrylate, monohydroxyethyl acrylate phthalate, and neopentyl glycol acrylate benzoate.
芳香環をもつ活性エネルギー硬化型モノマーの中でも、単官能モノマーが顔料分散体の低粘度化の実現できるため、好ましい。中でも、フェノキシエチルアクリレートは顔料分散体の低粘度化に加えて、理由は定かではないが、粘度の経時安定性が優れた顔料分散体の提供が可能であり、より好ましい。 Among the active energy curable monomers having an aromatic ring, a monofunctional monomer is preferable because the viscosity of the pigment dispersion can be reduced. Among them, phenoxyethyl acrylate is more preferable because it can provide a pigment dispersion having excellent viscosity stability over time, in addition to lowering the viscosity of the pigment dispersion.
また、芳香環をもつ活性エネルギー線硬化型モノマーは、紫外線などの活性エネルギー線を照射することで硬化する、活性エネルギー線硬化型インキを調製する上で好適である。 Moreover, the active energy ray-curable monomer having an aromatic ring is suitable for preparing an active energy ray-curable ink that is cured by irradiation with an active energy ray such as ultraviolet rays.
本発明の酸性顔料誘導体の基本骨格は、例えばＣ．Ｉ．ピグメントイエロー１２、１３、１４、１５、１６、１７、５５、８３、８７、１１３、１２４、１５２、１７１、１７２などのジスアゾイエロー顔料に類似した骨格をもつものや、Ｃ．Ｉ．ピグメントイエロー１３８のようなキノフタロンイエロー顔料に類似した骨格をもつものが好適である。 The basic skeleton of the acidic pigment derivative of the present invention is, for example, C.I. I. Pigment Yellow 12, 13, 14, 15, 16, 17, 55, 83, 87, 113, 124, 152, 171, 172 and the like having dissimilar skeletons such as C.I. I. Those having a skeleton similar to quinophthalone yellow pigment such as CI Pigment Yellow 138 are preferred.
上記酸性顔料誘導体は、上記顔料骨格に対しスルホン化処理を施したものであり、公知の方法にて合成することができる。 The acidic pigment derivative is obtained by sulfonating the pigment skeleton and can be synthesized by a known method.
上記酸性顔料誘導体は、単体、もしくは２種以上混合して使用してよく、顔料に対し０．１重量％以上１０重量％以下含有することが好ましい。０．１重量％未満であると、顔料に十分量吸着しないため充足な効果を発揮できず、１０重量％より多いと分散の安定性が悪くなり、インキ化後の保存安定性が悪化する場合がある。 The acidic pigment derivative may be used alone or in combination of two or more, and is preferably contained in an amount of 0.1% by weight to 10% by weight based on the pigment. When the amount is less than 0.1% by weight, a sufficient amount cannot be adsorbed on the pigment, so that a sufficient effect cannot be exhibited. When the amount is more than 10% by weight, the dispersion stability is deteriorated and the storage stability after inking is deteriorated. There is.
本発明の活性エネルギー線硬化型インクジェットインキには、従来既知の重合性モノマーやオリゴマー、プレポリマーを必要に応じて使用することができる。
前記を含め、活性エネルギー線硬化型モノマーの具体例としては、単官能モノマーとしてベンジル（メタ）アクリレート、(エトキシ(またはプロポキシ)化)２−フェノキシエチル（メタ）アクリレート、ジシクロペンテニル(オキシエチル) （メタ）アクリレート、フェノキシジエチレングリコール（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、メトキシトリエチレングリコール（メタ）アクリレート、２−エトキシエチル（メタ）アクリレート、エトキシエトキシエチル（メタ）アクリレート、メトキシジプロピレングリコール（メタ）アクリレート、ジプロピレングリコール（メタ）アクリレート、β-カルボキシルエチル（メタ）アクリレート、トリメチロールプロパンフォルマル（メタ）アクリレート、イソアミル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、テトラヒドロフルフリル（メタ）アクリレート、イソボロニル（メタ）アクリレート、ジシクロペンタニル（メタ）アクリレート、イソオクチル（メタ）アクリレート、ラウリル（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、１，４−シクロヘキサンジメタノール（メタ）アクリレート、２−ヒドロキシエチル（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、アクリロイルモルホリン、Ｎ−ビニルカプロラクタム、Ｎ−ビニルピロリドン、Ｎ-ビニルホルムアミド、Ｎ−アクリロイルオキシエチルヘキサヒドロフタルイミドを挙げることができる。
In the active energy ray-curable inkjet ink of the present invention, conventionally known polymerizable monomers, oligomers and prepolymers can be used as necessary.
Specific examples of the active energy ray-curable monomer including the above include benzyl (meth) acrylate, (ethoxy (or propoxy)) 2-phenoxyethyl (meth) acrylate, dicyclopentenyl (oxyethyl) (monofunctional monomer) (Meth) acrylate, phenoxydiethylene glycol (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxytriethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, ethoxyethoxyethyl (meth) acrylate, methoxydipropylene glycol (Meth) acrylate, dipropylene glycol (meth) acrylate, β-carboxylethyl (meth) acrylate, trimethylolpropane formal (meth) acrylate, isoamyl ( (Meth) acrylate, cyclohexyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isoboronyl (meth) acrylate, dicyclopentanyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, 2-hydroxy-3 -Phenoxypropyl (meth) acrylate, 1,4-cyclohexanedimethanol (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acryloylmorpholine, Mention may be made of N-vinylcaprolactam, N-vinylpyrrolidone, N-vinylformamide, N-acryloyloxyethylhexahydrophthalimide.
また多官能モノマーとしては、ジメチロール−トリシクロデカンジ（メタ）アクリレート、(エトキシ(またはプロポキシ)化)ビスフェノールＡジ（メタ）アクリレート、シクロヘキサンジメタノールジ（メタ）アクリレート、(ポリ)エチレングリコールジ（メタ）アクリレート、(エトキシ(またはプロポキシ)化) １，６−ヘキサンジオールジ（メタ）アクリレート、(エトキシ(またはプロポキシ)化)ネオペンチルグリコールジ（メタ）アクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、（ネオペンチルグリコール変性）トリメチロールプロパンジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート、ジシクロペンタニルジ（メタ）アクリレート、ペンタエリスリトールトリ(またはテトラ) （メタ）アクリレート、トリメチロールプロパントリ(またはテトラ) （メタ）アクリレート、テトラメチロールメタントリ(またはテトラ) （メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレートを挙げることができる。
以上の活性エネルギー線硬化型モノマーは、単独で用いられてもよいし、２種以上併用されてもよい。
Polyfunctional monomers include dimethylol-tricyclodecane di (meth) acrylate, (ethoxy (or propoxy)) bisphenol A di (meth) acrylate, cyclohexanedimethanol di (meth) acrylate, (poly) ethylene glycol di ( (Meth) acrylate, (ethoxy (or propoxy)) 1,6-hexanediol di (meth) acrylate, (ethoxy (or propoxy)) neopentyl glycol di (meth) acrylate, hydroxypivalate neopentyl glycol di (meth) ) Acrylate, dipropylene glycol di (meth) acrylate, (neopentyl glycol modified) trimethylolpropane di (meth) acrylate, tripropylene glycol di (meth) acrylate, dicyclopentanyl di (meth) a Relate, pentaerythritol tri (or tetra) (meth) acrylate, trimethylolpropane tri (or tetra) (meth) acrylate, tetramethylolmethane tri (or tetra) (meth) acrylate, dipentaerythritol hexa (meth) acrylate be able to.
The above active energy ray-curable monomers may be used alone or in combination of two or more.
このうち本発明のインクジェットインキにおいては、単官能モノマーとしてフェノキシエチルアクリレート、エトキシエトキシエチルアクリレート、イソボロニルアクリレート、イソオクチルアクリレート、ラウリルアクリレート、Ｎ−ビニルカプロラクタム、Ｎ−アクリロイルオキシエチルヘキサヒドロフタルイミドを、また多官能モノマーとしてジメチロールートリシクロデカンジアクリレート、(エトキシ(またはプロポキシ)化)ビスフェノールＡジアクリレート、(エトキシ(またはプロポキシ)化)ネオペンチルグリコールジアクリレート、ヒドロキシピバリン酸ネオペンチルグリコールジアクリレート、１，６−ヘキサンジオールジアクリレート、ジプロピレングリコールジアクリレート、トリプロピレングリコールジアクリレートをより好適に用いることができる。 Among these, in the inkjet ink of the present invention, phenoxyethyl acrylate, ethoxyethoxyethyl acrylate, isobornyl acrylate, isooctyl acrylate, lauryl acrylate, N-vinylcaprolactam, N-acryloyloxyethyl hexahydrophthalimide as monofunctional monomers, Further, dimethylol-tricyclodecane diacrylate, (ethoxy (or propoxy)) bisphenol A diacrylate, (ethoxy (or propoxy)) neopentyl glycol diacrylate, hydroxypivalate neopentyl glycol diacrylate, 1,6-hexanediol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate It can be suitably used.
本発明の活性エネルギー線硬化型インクジェットインキには、上記以外にオリゴマー、プレポリマーと呼ばれるものを使用できる。具体的には、ダイセルＵＣＢ社製「Ｅｂｅｃｒｙｌ２３０、２４４、２４５、２７０、２８０／１５ＩＢ、２８４、２８５、４８３０、４８３５、４８５８、４８８３、８４０２、８８０３、８８００、２５４、２６４、２６５、２９４／３５ＨＤ、１２５９、１２６４、４８６６、９２６０、８２１０、１２９０．１２９０Ｋ、５１２９、２０００、２００１、２００２、２１００、ＫＲＭ７２２２、ＫＲＭ７７３５、４８４２、２１０、２１５、４８２７、４８４９、６７００、６７００−２０Ｔ、２０４、２０５、６６０２、２２０、４４５０、７７０、ＩＲＲ５６７、８１、８４、８３、８０、６５７、８００、８０５、８０８、８１０、８１２、１６５７、１８１０、ＩＲＲ３０２、４５０、６７０、８３０、８３５、８７０、１８３０、１８７０、２８７０、ＩＲＲ２６７、８１３、ＩＲＲ４８３、８１１、４３６、４３８、４４６、５０５、５２４、５２５、５５４Ｗ、５８４、５８６、７４５、７６７、１７０１、１７５５、７４０／４０ＴＰ、６００、６０１、６０４、６０５、６０７、６０８、６０９、６００／２５ＴＯ、６１６、６４５、６４８、８６０、１６０６、１６０８、１６２９、１９４０、２９５８、２９５９、３２００、３２０１、３４０４、３４１１、３４１２、３４１５、３５００、３５０２、３６００、３６０３、３６０４、３６０５、３６０８、３７００、３７００−２０Ｈ、３７００−２０Ｔ、３７００−２５Ｒ、３７０１、３７０１−２０Ｔ、３７０３、３７０２、ＲＤＸ６３１８２、６０４０、ＩＲＲ４１９」、サートマー社製「ＣＮ１０４、ＣＮ１２０、ＣＮ１２４、ＣＮ１３６、ＣＮ１５１、ＣＮ２２７０、ＣＮ２２７１Ｅ、ＣＮ４３５、ＣＮ４５４、ＣＮ９７０、ＣＮ９７１、ＣＮ９７２、ＣＮ９７８２、ＣＮ９８１、ＣＮ９８９３、ＣＮ９９１」、ＢＡＳＦ社製「Ｌａｒｏｍｅｒ ＥＡ８１、ＬＲ８７１３、ＬＲ８７６５、ＬＲ８９８６、ＰＥ５６Ｆ、ＰＥ４４Ｆ、ＬＲ８８００、ＰＥ４６Ｔ、ＬＲ８９０７、ＰＯ４３Ｆ、ＰＯ７７Ｆ、ＰＥ５５Ｆ、ＬＲ８９６７、ＬＲ８９８１、ＬＲ８９８２、ＬＲ８９９２、ＬＲ９００４、ＬＲ８９５６、ＬＲ８９８５、ＬＲ８９８７、ＵＰ３５Ｄ、ＵＡ１９Ｔ、ＬＲ９００５、ＰＯ８３Ｆ、ＰＯ３３Ｆ、ＰＯ８４Ｆ、ＰＯ９４Ｆ、ＬＲ８８６３、ＬＲ８８６９、ＬＲ８８８９、ＬＲ８９９７、ＬＲ８９９６、ＬＲ９０１３、ＬＲ９０１９、ＰＯ９０２６Ｖ、ＰＥ９０２７Ｖ」、コグニス社製「フォトマー３００５、３０１５、３０１６、３０７２、３９８２、３２１５、５０１０、５４２９、５４３０、５４３２、５６６２、５８０６、５９３０、６００８、６０１０、６０１９、６１８４、６２１０、６２１７、６２３０、６８９１、６８９２、６８９３−２０Ｒ、６３６３、６５７２、３６６０」、根上工業社製「アートレジンＵＮ−９０００ＨＰ、９０００ＰＥＰ、９２００Ａ、７６００、５２００、１００３、１２５５、３３２０ＨＡ、３３２０ＨＢ、３３２０ＨＣ、３３２０ＨＳ、９０１Ｔ、１２００ＴＰＫ、６０６０ＰＴＭ、６０６０Ｐ」、日本合成化学社製「紫光 ＵＶ−６６３０Ｂ、７０００Ｂ、７５１０Ｂ、７４６１ＴＥ、３０００Ｂ、３２００Ｂ、３２１０ＥＡ、３３１０Ｂ、３５００ＢＡ、３５２０ＴＬ、３７００Ｂ、６１００Ｂ、６６４０Ｂ、１４００Ｂ、１７００Ｂ、６３００Ｂ、７５５０Ｂ、７６０５Ｂ、７６１０Ｂ、７６２０ＥＡ、７６３０Ｂ、７６４０Ｂ、２０００Ｂ、２０１０Ｂ、２２５０ＥＡ、２７５０Ｂ」、日本化薬社製「カヤラッドＲ−２８０、Ｒ−１４６、Ｒ１３１、Ｒ−２０５、ＥＸ２３２０，Ｒ１９０、Ｒ１３０、Ｒ−３００，Ｃ−００１１、ＴＣＲ−１２３４、ＺＦＲ−１１２２、ＵＸ−２２０１，ＵＸ−２３０１，ＵＸ３２０４、ＵＸ−３３０１、ＵＸ−４１０１，ＵＸ−６１０１、ＵＸ−７１０１、ＭＡＸ−５１０１、ＭＡＸ−５１００，ＭＡＸ−３５１０、ＵＸ−４１０１」などを挙げることができるがこれに限定されるものではない。 In addition to the above, what is called an oligomer or a prepolymer can be used for the active energy ray-curable inkjet ink of the present invention. Specifically, “Ebecryl 230, 244, 245, 270, 280 / 15IB, 284, 285, 4830, 4835, 4858, 4883, 8402, 8803, 8800, 254, 264, 265, 294 / 35HD, manufactured by Daicel UCB, 1259, 1264, 4866, 9260, 8210, 1290.1290K, 5129, 2000, 2001, 2002, 2100, KRM7222, KRM7735, 4842, 210, 215, 4827, 4849, 6700, 6700-20T, 204, 205, 6602, 220, 4450, 770, IRR567, 81, 84, 83, 80, 657, 800, 805, 808, 810, 812, 1657, 1810, IRR302, 450, 670, 830, 835, 870, 1 30, 1870, 2870, IRR267, 813, IRR483, 811, 436, 438, 446, 505, 524, 525, 554W, 584, 586, 745, 767, 1701, 1755, 740 / 40TP, 600, 601, 604, 605, 607, 608, 609, 600 / 25TO, 616, 645, 648, 860, 1606, 1608, 1629, 1940, 2958, 2959, 3200, 3201, 3404, 3411, 3412, 3415, 3500, 3502, 3600, 3603, 3604, 3605, 3608, 3700, 3700-20H, 3700-20T, 3700-25R, 3701, 3701-20T, 3703, 3702, RDX63182, 6040, IRR419 ", manufactured by Sartomer CN104, CN120, CN124, CN136, CN151, CN2270, CN2271E, CN435, CN454, CN970, CN971, CN972, CN9782, CN981, CN9873, CN991, "Laromar EA81L, F87" manufactured by BASF LR8800, PE46T, LR8907, PO43F, PO77F, PE55F, LR8967, LR8981, LR8982, LR8992, LR9004, LR8956, LR8985, LR8987, UP35D, UA19T, LR9005, PO83F, PO33F, L8489, L9489 LR8996, LR9013 LR9019, PO9026V, PE9027V "manufactured by Cognis" Photomer 3005, 3015, 3016, 3072, 3982, 3215, 5010, 5429, 5430, 5432, 5662, 5806, 5930, 6008, 6010, 6019, 6184, 6210, 6217, 6230, 6891, 6892, 6893-20R, 6363, 6572, 3660 "," Art Resin UN-9000HP, 9000PEP, 9200A, 7600, 5200, 1003, 1255, 3320HA, 3320HB, 3320HC, 3320HS, 901T, manufactured by Negami Kogyo Co., Ltd. 1200TPK, 6060PTM, 6060P "," Nippon Gosei Chemical Co., Ltd. "" purple light UV-6630B, 7000B, 7510B, 7461TE, 3000B, 320 " 0B, 3210EA, 3310B, 3500BA, 3520TL, 3700B, 6100B, 6640B, 1400B, 1700B, 6300B, 7550B, 7605B, 7610B, 7620EA, 7630B, 7640B, 2000B, 2010B, 2250EA, 2750B, “Kayarad” R-280, R-146, R131, R-205, EX2320, R190, R130, R-300, C-0011, TCR-1234, ZFR-1122, UX-2201, UX-2301, UX3204, UX-3301, UX-4101, UX-6101, UX-7101, MAX-5101, MAX-5100, MAX-3510, UX-4101 ", etc., but are not limited thereto.
本発明において紫外線等の活性エネルギー線を用いてインキを硬化させる場合には、光重合開始剤を配合する。本発明で用いることができる光重合開始剤としては公知の光重合開始剤を使用することができ、分子開裂型や水素引き抜き型でラジカルを発生させる光重合開始剤を使用することが好ましい。本発明に用いることができる光重合開始剤は、単独で使用してもよく、２種以上を併用してもよい。また、ラジカルを発生させる光重合開始剤とカチオンを発生させる光重合開始剤とを併用してもよい。 In the present invention, when the ink is cured using an active energy ray such as ultraviolet rays, a photopolymerization initiator is blended. As the photopolymerization initiator that can be used in the present invention, a known photopolymerization initiator can be used, and it is preferable to use a photopolymerization initiator that generates a radical in a molecular cleavage type or a hydrogen abstraction type. The photopolymerization initiator that can be used in the present invention may be used alone or in combination of two or more. Further, a photopolymerization initiator that generates radicals and a photopolymerization initiator that generates cations may be used in combination.
光重合開始剤の具体例としては、２，２−ジメトキシ−１，２−ジフェニルエタン−１−オン、１−ヒドロキシ−シクロヘキシル−フェニル−ケトン、２−ヒドロキシ−２−メチル−１−フェニル−プロパン−１−オン、１−［４−（２−ヒドロキシエトキシ）−フェニル］−２−ヒドロキシ−２−メチル−１−プロパン−１−オン、２−ヒドロキシ−１−｛４−［４−（２−ヒドロキシ−２−メチル−プロピオニル）−ベンジル］−フェニル｝−２−メチル−プロパン−１−オン、フェニルグリオキシリックアシッドメチルエステル、２−メチル−１−［４−（メチルチオ）フェニル］−２−モルフォリノプロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタノン−１、２−ジメチルアミノ−２−（４−メチル−ベンジル）−１−（４−モルフォリン−４−イル−フェニル）−ブタノン−１−オン、ビス（２，４，６−トリメチルベンゾイル）−フェニルフォスフィンオキサイド、２，４，６−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド、１，２−オクタンジオン、１−［４−（フェニルチオ）−、２−（Ｏ−ベンゾイルオキシム）］、エタノン、１−［９−エチル−６−（２−メチルベンゾイル）−９Ｈ−カルバゾール−３−イル］−、１−（Ｏ−アセチルオキシム）、ベンゾフェノン、４−フェニルベンゾフェノン、イソフタルフェノン、４−ベンゾイル−４'−メチル−ジフェニルスルフィドなどを挙げることができるがこれに限定されるものではない。 Specific examples of the photopolymerization initiator include 2,2-dimethoxy-1,2-diphenylethane-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy-2-methyl-1-phenyl-propane. -1-one, 1- [4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, 2-hydroxy-1- {4- [4- (2 -Hydroxy-2-methyl-propionyl) -benzyl] -phenyl} -2-methyl-propan-1-one, phenylglyoxylic acid methyl ester, 2-methyl-1- [4- (methylthio) phenyl] -2 -Morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1,2-dimethylamino 2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butanone-1-one, bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2, 4,6-trimethylbenzoyl-diphenyl-phosphine oxide, 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime)], ethanone, 1- [9-ethyl-6 -(2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), benzophenone, 4-phenylbenzophenone, isophthalphenone, 4-benzoyl-4'-methyl-diphenyl sulfide, etc. However, the present invention is not limited to this.
また上記光重合開始剤に対し、増感剤として例えば、トリメチルアミン、メチルジメタノールアミン、トリエタノールアミン、ｐ−ジエチルアミノアセトフェノン、ｐ−ジメチルアミノ安息香酸エチル、ｐ−ジメチルアミノ安息香酸イソアミル、Ｎ，Ｎ−ジメチルベンジルアミンおよび４，４'−ビス（ジエチルアミノ）ベンゾフェノン等を併用することもできる。もちろん、上記光重合開始剤や増感剤は、活性エネルギー線硬化性化合物への溶解性に優れ、紫外線透過性を阻害しないものを選択して用いることが好ましい。 For the above photopolymerization initiator, for example, trimethylamine, methyldimethanolamine, triethanolamine, p-diethylaminoacetophenone, ethyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, N, N -Dimethylbenzylamine and 4,4'-bis (diethylamino) benzophenone can also be used in combination. Of course, it is preferable to select and use the photopolymerization initiator and the sensitizer that are excellent in solubility in the active energy ray-curable compound and do not inhibit the ultraviolet light transmittance.
上記光重合開始剤は、重合性モノマーに対し、２〜２０重量％含有することが好ましい。２重量％未満であると硬化性が著しく悪化し、２０重量％より多いと、含有量が２０重量％のものと硬化性が変わらないばかりか、溶解残りが発生する場合がありインクジェット吐出性が悪化する、低温で光重合開始剤が析出する、といった問題がある。
本発明のインク組成物は、ヘッドでの詰まりを防止するため、分散後および／または光ラジカル重合開始剤の溶解後に、孔径３μｍ以下、好ましくは孔径１μ以下のフィルターにて濾過することが好ましい。
以下実施例および比較例により本発明をさらに具体的に説明するが、本発明の態様がこれらの例に限定されるものではない。また下記の実施例、比較例の詳細な条件を以下の表１、３に、結果を表２、４に示す。なお以下の表中の数字は、全て重量部を表す。
The photopolymerization initiator is preferably contained in an amount of 2 to 20% by weight based on the polymerizable monomer. If it is less than 2% by weight, the curability is remarkably deteriorated, and if it is more than 20% by weight, not only the curability will be the same as that having a content of 20% by weight. There is a problem that the photopolymerization initiator is precipitated at a low temperature.
In order to prevent clogging in the head, the ink composition of the present invention is preferably filtered through a filter having a pore size of 3 μm or less, preferably 1 μm or less after dispersion and / or after dissolution of the radical photopolymerization initiator.
Hereinafter, the present invention will be described more specifically with reference to examples and comparative examples, but the embodiments of the present invention are not limited to these examples. The detailed conditions of the following Examples and Comparative Examples are shown in Tables 1 and 3 below, and the results are shown in Tables 2 and 4. The numbers in the following table all represent parts by weight.
※酸性顔料誘導体Ａ：ジスアゾ骨格をもつ酸性顔料誘導体
酸性顔料誘導体Ｂ：キノフタロン骨格をもつ酸性顔料誘導体
酸性顔料誘導体Ｃ：ジスアゾ骨格をもち、且つ、誘導体Ａとは異なる構造をもつ
ＰＥＡ：フェノキシエチルアクリレート
ＩＯＡ：イソオクチルアクリレート
ＢＧＤＡ：１,３-ブチレングリコールジアセテート
イエロー顔料分散体は、表１に記載した材料をハイスピードミキサーで均一になるまで攪拌後、得られたミルベースをダイノミルで分散した。分散は、径１ｍｍのジルコニアビーズを充填した。分散時間に関して特に制限はないが、今回は２．５〜３．５時間が好適だった。
実施例１〜７、比較例１〜５で作製した顔料分散体を４５℃で１週間保管し、経時保管前後での粘度を評価した。
* Acid pigment derivative A: Acid pigment derivative with disazo skeleton
Acid pigment derivative B: Acid pigment derivative having a quinophthalone skeleton
Acid pigment derivative C: has a disazo skeleton and a structure different from that of derivative A
PEA: Phenoxyethyl acrylate IOA: Isooctyl acrylate BGDA: 1,3-butylene glycol diacetate yellow pigment dispersion was prepared by stirring the materials listed in Table 1 with a high-speed mixer until uniform, and then converting the resulting mill base to Dino mill Dispersed. The dispersion was filled with zirconia beads having a diameter of 1 mm. Although there is no particular limitation on the dispersion time, 2.5 to 3.5 hours were suitable this time.
The pigment dispersions prepared in Examples 1 to 7 and Comparative Examples 1 to 5 were stored at 45 ° C. for 1 week, and the viscosities before and after storage with time were evaluated.
経時保管前後の顔料分散体は、Ｅ型粘度計を使用し２５℃にて粘度を測定した。このときの評価基準は以下の通りである。
◎：初期粘度、経時粘度ともに良好
○：初期粘度良好、経時粘度並
△：初期粘度、経時粘度どちらか一方不良
×：初期粘度、経時粘度ともに不良、またはゲル化
経時粘度は、初期粘度に対する粘度変化率を基準に評価した。具体的には、下記式にて算出した。
The pigment dispersion before and after storage with time was measured for viscosity at 25 ° C. using an E-type viscometer. The evaluation criteria at this time are as follows.
◎: Good initial viscosity and time-dependent viscosity ○: Good initial viscosity, average time-dependent viscosity △: Poor initial viscosity or time-dependent viscosity ×: Poor initial viscosity or time-dependent viscosity, or gelation time-dependent viscosity is the viscosity relative to the initial viscosity Evaluation was based on the rate of change. Specifically, it was calculated by the following formula.
粘度変化率（％）＝｛（４５℃１週間保管後の粘度値）−（初期粘度値）｝
／（初期粘度値）×１００
計算の結果、粘度変化率が１０％未満だと良好、１０％以上５０％未満なら並、５０％以上又はゲル化した場合は不良と判断した。
Viscosity change rate (%) = {(viscosity value after storage at 45 ° C. for 1 week) − (initial viscosity value)}
/ (Initial viscosity value) × 100
As a result of calculation, when the rate of change in viscosity was less than 10%, it was judged that it was good if it was 10% or more and less than 50%.
イエロー顔料分散体の評価結果を表２に示した。実施例２が最も好適な条件であったが、実施例１〜７いずれも総じて良好な傾向だった。実施例８では酸性顔料誘導体を過剰に加えたが、良好な傾向だった。一方で比較例１は分散媒をＩＯＡに変更したものであり、ＩＯＡが低粘度であることもあり初期粘度は良好だったが、経時保管後の粘度は大きく増粘した。比較例２、３は、初期粘度、経時保管後の粘度がともに高く、比較例４は初期条件でゲル化した。 The evaluation results of the yellow pigment dispersion are shown in Table 2. Example 2 was the most suitable condition, but all of Examples 1 to 7 were generally good. In Example 8, the acidic pigment derivative was added excessively, but the tendency was good. On the other hand, in Comparative Example 1, the dispersion medium was changed to IOA, and the initial viscosity was good because IOA was low viscosity, but the viscosity after storage with time was greatly increased. In Comparative Examples 2 and 3, both the initial viscosity and the viscosity after storage with time were high, and Comparative Example 4 gelled under the initial conditions.
ＤＰＧＤＡ：ジプロピレングリコールジアクリレート
（コグニス社製「ＰＨＯＴＯＭＥＲ４２２６」）
ＴＰＧＤＡ：トリプロピレングリコールジアクリレート
（大阪有機化学工業社製「Ｖ＃３１０ＨＰ」）
ＵＫ４１０１：ヒドロキシピバリン酸ネオペンチルグリコールジアクリレート
（三菱レイヨン社製「ダイヤビーム ＵＫ−４１０１」）
ＩＲＧＡＣＵＲＥ ３６９
：２−ベンジル−２−ジメチルアミノ−１−（４−モルフォリノフェニル）−ブタン−１−オン
（ＢＡＳＦ社製）
ＩＲＧＡＣＵＲＥ ８１９
：ビス（２、４、６−ジメトキシベンゾイル）−２、４、４−トリメチルペンチルフォスフィンオキシド
（ＢＡＳＦ社製）
ＩＲＧＡＣＵＲＥ ９０７
：２−メチル−１−（４−メチルチオフェニル）−２−モルフォリノプロパン−１−オン
（ＢＡＳＦ社製）
ＤＡＲＯＣＵＲ ＴＰＯ
：２，４，６−トリメチルベンゾイルジフェニルフォスフィンオキシド
（ＢＡＳＦ社製）
ＫＡＹＡＣＵＲＥ ＢＭＳ
：４−ベンゾイル−４'−メチル−ジフェニルスルフィド
（日本化薬（株）製）
ＳＢ−ＰＩ ７０４
：エチル−４−（ジメチルアミノ）−ベンゾエート
（サートマー社製）
実施例８〜２３のインクジェットインキを６０℃で１週間保管し、経時保管前後の粘度を評価した。
経時保管前後のインクジェットインキは、Ｅ型粘度計を使用し２５℃にて粘度を測定した。このときの評価基準は以下の通りである。
◎：初期粘度、経時粘度ともに良好
○：初期粘度良好、経時粘度並
△：初期粘度、経時粘度どちらか一方不良
×：初期粘度、経時粘度ともに不良、またはゲル化
経時粘度は、上記の顔料分散体経時粘度評価同様に、初期粘度に対する粘度変化率を基準に評価した。具体的には、上記同様に下記式にて算出した。
DPGDA: Dipropylene glycol diacrylate
("PHOTOMER 4226" manufactured by Cognis)
TPGDA: Tripropylene glycol diacrylate
(“V # 310HP” manufactured by Osaka Organic Chemical Industry Co., Ltd.)
UK4101: Hydroxypivalic acid neopentyl glycol diacrylate
("Diabeam UK-4101" manufactured by Mitsubishi Rayon Co., Ltd.)
IRGACURE 369
: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one (manufactured by BASF)
IRGACURE 819
: Bis (2,4,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide (manufactured by BASF)
IRGACURE 907
: 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (manufactured by BASF)
DAROCUR TPO
: 2,4,6-trimethylbenzoyldiphenylphosphine oxide (manufactured by BASF)
KAYACURE BMS
: 4-benzoyl-4'-methyl-diphenyl sulfide (manufactured by Nippon Kayaku Co., Ltd.)
SB-PI 704
: Ethyl-4- (dimethylamino) -benzoate (manufactured by Sartomer)
The inkjet inks of Examples 8 to 23 were stored at 60 ° C. for 1 week, and the viscosities before and after storage with time were evaluated.
The ink-jet ink before and after storage with time was measured for viscosity at 25 ° C. using an E-type viscometer. The evaluation criteria at this time are as follows.
◎: Good initial viscosity and time-dependent viscosity ○: Good initial viscosity, average time-dependent viscosity △: Poor initial viscosity or time-dependent viscosity X: Poor initial viscosity or time-dependent viscosity, or gelation time-dependent viscosity is the above pigment dispersion Similar to the evaluation of body viscosity with time, the viscosity change rate relative to the initial viscosity was evaluated as a reference. Specifically, it calculated with the following formula similarly to the above.
粘度変化率（％）＝｛（６０℃１週間保管後の粘度値）−（初期粘度値）｝
／（初期粘度値）×１００
計算の結果、粘度変化率が５％未満だと良好、５％以上１０％未満なら並、１０％以上は不良と判断した。
Viscosity change rate (%) = {(viscosity value after storage at 60 ° C. for 1 week) − (initial viscosity value)}
/ (Initial viscosity value) × 100
As a result of the calculation, it was judged that if the rate of change in viscosity was less than 5%, it was good if it was 5% or more and less than 10%.
インクジェットインキの実施例を８〜２３に示した。いずれもインキ化すると初期粘度良好、経時保管後の粘度が並以上だった。中でも、酸性顔料誘導体を使用した実施例１０〜１５及び１８〜２１が経時保管後も増粘が抑えられる傾向にあった。また、酸性顔料誘導体過剰の実施例２２、２３は、経時保管後の粘度が不良であった。
Examples of inkjet ink are shown in 8-23. In any case, the initial viscosity was good when converted to ink, and the viscosity after storage over time was above normal. Especially, Examples 10-15 and 18-21 using an acidic pigment derivative tended to suppress thickening even after storage over time. In addition, Examples 22 and 23 in which the acidic pigment derivative was excessive had poor viscosity after storage over time.
Claims (4)
An active energy ray-curable inkjet ink comprising the yellow pigment dispersion according to claim 1.
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| JP2015059157A (en) * | 2013-09-18 | 2015-03-30 | Dic株式会社 | Active energy ray-curable inkjet recording ink |
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