US20080097005A1 - Ink Composition for Inkjet Printing - Google Patents
Ink Composition for Inkjet Printing Download PDFInfo
- Publication number
- US20080097005A1 US20080097005A1 US11/660,445 US66044505A US2008097005A1 US 20080097005 A1 US20080097005 A1 US 20080097005A1 US 66044505 A US66044505 A US 66044505A US 2008097005 A1 US2008097005 A1 US 2008097005A1
- Authority
- US
- United States
- Prior art keywords
- ink
- ink composition
- ether
- glycol
- jet printing
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 68
- 238000007641 inkjet printing Methods 0.000 title claims abstract description 34
- 239000000049 pigment Substances 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 lactone compound Chemical class 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 13
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 239000002270 dispersing agent Substances 0.000 claims abstract description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 14
- 229920006122 polyamide resin Polymers 0.000 claims description 13
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 11
- 229920006026 co-polymeric resin Polymers 0.000 claims description 11
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical group COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000005215 alkyl ethers Chemical class 0.000 claims 8
- 238000007639 printing Methods 0.000 abstract description 16
- 238000011161 development Methods 0.000 abstract description 5
- 238000001035 drying Methods 0.000 abstract description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000976 ink Substances 0.000 description 60
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000002950 deficient Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 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
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-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
- KXJGSNRAQWDDJT-UHFFFAOYSA-N 1-acetyl-5-bromo-2h-indol-3-one Chemical compound BrC1=CC=C2N(C(=O)C)CC(=O)C2=C1 KXJGSNRAQWDDJT-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-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
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- CKCGJBFTCUCBAJ-UHFFFAOYSA-N 2-(2-ethoxypropoxy)propyl acetate Chemical compound CCOC(C)COC(C)COC(C)=O CKCGJBFTCUCBAJ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920001747 Cellulose diacetate Polymers 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 241000721047 Danaus plexippus Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 229920003064 carboxyethyl cellulose Polymers 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
Definitions
- the present invention relates to an ink composition for ink-jet printing and, more particularly, to an ink composition for ink-jet printing which does not cause clogging of nozzles of an ink-jet printer during printing, to thereby provide a print of desired printing quality; which ensures an appropriate drying rate of printed images; and which attains excellent color development.
- the present invention has been conceived in order to solve the aforementioned problems, and an object of the present invention is to provide an ink composition for ink-jet printing which does not cause clogging of nozzles of an ink-jet printer during printing, to thereby provide a print of desired printing quality; which ensures an appropriate drying rate of printed images; and which attains excellent color development.
- the present inventors have carried out extensive studies in order to attain the aforementioned object, and have found that an excellent ink composition for ink-jet printing can be produced through employment of a solvent having a predetermined composition.
- the present invention has been accomplished on the basis of this finding.
- the present invention provides an ink composition for ink-jet printing, comprising a pigment, a binder resin, a pigment dispersant, and a solvent, characterized in that the solvent is formed of
- the solvent employed is formed of (1) at least one glycol ether and at least one of a lactone compound and 2-pyrrolidone, or (2) at least one glycol ether acetate and at least one of cyclohexane and isophorone.
- the amount of the solvent mixture which is determined in consideration of factors such as viscosity and surface tension of the ink composition, is generally 60 to 99 mass % on the basis of the ink composition, preferably 80 to 97 mass %.
- the amount thereof is 15 to 95 mass % on the basis of the ink composition, preferably 55 to 85 mass %, and at least one of a lactone compound and 2-pyrrolidone is used in an amount of 1 to 45 mass % on the basis of the ink composition, preferably 10 to 25 mass %.
- the amount thereof is 15 to 90 mass % on the basis of the ink composition, preferably 55 to 85 mass %, and at least one of cyclohexanone and isophorone is used in an amount of 0.5 to 30 mass % on the basis of the ink composition, preferably 1 to 25 mass %.
- glycol ether employed in the present invention examples include ethylene glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol diethyl ether, and triethylene glycol monobutyl ether; propylene glycol ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, propylene glycol dimethyl ether, dipropylene glycol dimethyl ether, propylene glycol diethyl ether, and dipropylene glycol diethyl ether; and mixtures thereof.
- ethylene glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monobut
- lactone compound employed in the present invention examples include ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -valerolactone, and mixtures thereof.
- glycol ether acetate employed in the present invention examples include ethylene glycol ether acetates such as ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and ethylene glycol monobutyl ether acetate; and propylene glycol ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate; and mixtures thereof.
- ethylene glycol ether acetates such as ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and ethylene glycol monobutyl ether acetate
- propylene glycol ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diprop
- the ink composition of the present invention for ink-jet printing contains a binder resin.
- the binder resin is particularly preferably vinyl chloride copolymer resin.
- vinyl chloride copolymer resin may be used singly or in combination with other resins.
- the amount of the binder resin which is determined in consideration of factors such as fixability, viscosity and surface tension of the ink composition, is generally 0.5 to 15 mass % on the basis of the ink composition, preferably 1 to 10 mass %.
- vinyl chloride resins may be employed. Specific examples include vinyl chloride copolymer resins with other co-monomers such as vinyl acetate, vinylidene chloride, acrylic monomer, and maleic acid.
- a preferred vinyl chloride copolymer resin is a vinyl chloride-vinyl acetate copolymer resin formed through copolymerization of vinyl chloride and vinyl acetate, and such a copolymer resin having a molecular weight of 30,000 or less is particularly preferred.
- any resins employed in conventional ink compositions may be used.
- the resins include epoxy resin, phenolic resin, novolak resin, acrylic resin, rosin-modified phenolic resin, polyester resin, amino resins (melamine resin, benzoguanamine resin, etc.), polyamide resin, cellulose ester resins (cellulose diacetate, cellulose triacetate, nitrocellulose, cellulose nitrate, cellulose propionate, cellulose acetate butyrate, etc.), cellulose ether resins (methyl cellulose, ethyl cellulose, benzyl cellulose, trityl cellulose, cyanoethyl cellulose, carboxymethyl cellulose, carboxyethyl cellulose, aminoethyl cellulose, etc.), and vinyl acetate copolymer resins.
- pigment employed in the ink composition of the present invention for ink-jet printing examples include Pigment Yellow 12, 13, 14, 17, 20, 24, 31, 55, 74, 83, 86, 93, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 155, 166, 168, 180, 181, and 185; Pigment Orange 16, 36, 38, 43, 51, 55, 59, 61, 64, 65, and 71; Pigment Red 9, 48, 49, 52, 53, 57, 97, 122, 123, 149, 168, 177, 180, 192, 202, 206, 215, 216, 217, 220, 223, 224, 226, 227, 228, 238, 240, 244, and 254; Pigment Violet 19, 23, 29, 30, 32, 37, 40, and 50; Pigment Blue 15, 15:1, 15:3, 15:4, 15:6, 22, 30, 64, and 80; Pigment Green 7 and 36; Pigment Green
- Examples of the pigment dispersant employed in the ink composition of the present invention for ink-jet printing include a polyester-polyamide resin having two or more amido groups in the one molecule thereof and a number-average molecular weight of 2,000 to 15,000.
- the amount of the pigment dispersant incorporated into the composition is generally 0.1 to 15 mass % on the basis of the ink composition, preferably 0.5 to 10 mass %.
- a typical example of the pigment dispersant is produced through reaction of an acid-terminated polyester resin with a polyamine compound having two or more amino groups in the one molecule thereof.
- Specific examples include Solsperse 32000, Solsperse 32500, Solsperse 32600, Solsperse 33500, Solsperse 34750, Solsperse 35100, Solsperse 37500, and Disperbyk 9077.
- a polyester-polyamide resin having one or no amido group in the one molecule thereof is not preferred, since pigment dispersion is poor.
- the number-average molecular weight is less than 2,000, stable dispersion of pigment cannot be attained, whereas when the number-average molecular weight is in excess of 15,000, dispersibility of the pigment in ink tends to decrease.
- the ink composition of the present invention for ink-jet printing may further contain a conductivity-controlling agent.
- the amount of the conductivity-controlling agent incorporated into the composition is generally 0.1 to 10 mass % on the basis of the ink composition, preferably 0.5 to 5 mass %.
- the ink composition of the present invention preferably has a viscosity (20° C.) of 1 to 100 cP, a surface tension of 2 ⁇ 10 ⁇ 2 to 6 ⁇ 10 ⁇ 2 N/m, and a specific weight of 0.8 to 1.2.
- the ink composition of the present invention for ink-jet printing may be prepared by mixing/stirring of the starting components, and filtering for purifying the mixture by means of a filter having a pore size about 1/10 or less of the nozzle size of the ink jet printer employed.
- the ink composition of the present invention for ink-jet printing may be used with a variety of ink-jet printers; e.g., a charge controlling type ink-jet printer and a drop-on-demand type ink-jet printer.
- the ink composition of the present invention is suitably employed in printing by means of a large-format ink-jet printer; e.g., an ink-jet printer for printing outdoor articles such as sign displays.
- a large-format ink-jet printer e.g., an ink-jet printer for printing outdoor articles such as sign displays.
- the printed surface (ink composition) on a substrate forms dry film by drying it at ambient temperature to several hundreds of degrees celsius.
- the substrate on which the ink composition is printed no particular limitation is imposed on the substrate on which the ink composition is printed, so long as the substrate is not deformed or decayed under the conditions where the printed surface (ink composition) is dried.
- substrates include substrates made of metal, glass, or plastic material; resin-coated paper, transparent sheets for overhead projection; and outdoor articles such as sign displays.
- the ink composition of the present invention for ink-jet printing, clogging of nozzles of an ink-jet printer which would otherwise occur during printing is prevented. Therefore, a print of desired printing quality can be obtained, and an appropriate drying rate of printed images and excellent color development can be attained.
- Inks of Examples 1 to 4 and Comparative Examples 1 to 3 were prepared by kneading, by means of a sand mill, for three hours, respective mixtures containing components in respective amounts (parts by mass) shown in Table 1.
- Monarch 1000 carbon black, product of Cabot Corp.
- VYHD vinyl chloride copolymer resin, product of Dow Chemical Co.
- CAB-551-0.01 cellulose ester resin, product of Eastman
- Solsperse 37500 polyyester-polyamide resin (solid content: 40%), product of Avecia
- Disperbyk 167 polyamide resin (solid content: 52%), product of Byk-Chemie).
- Example 1 to 4 and Comparative Examples 1 to 3 were analyzed in terms of viscosity, particle size, dispersion stability, nozzle clogging, and resistance to ethanol, through the following methods. These properties were evaluated according to the following ratings.
- SALD-7000 laser diffraction particle size distribution meter
- a test image was obtained by means of a large-format ink-jet printer, and the obtained image was visually assessed.
- the print condition was evaluated according to the following ratings.
- a test image was obtained by means of a large-format ink-jet printer, and the obtained image was rubbed with a piece of cloth impregnated with 50 mass % ethanol-water. The thus-treated image was visually assessed.
- the ink of Comparative Example 1 employing a solvent mixture falling outside the scope of the invention caused nozzle clogging and provided defective images.
- the ink of Comparative Example 2 employing only one species of the essential two solvents of the invention exhibited poor dispersion stability and caused clogging of nozzles, thereby providing defective images.
- the ink of Comparative Example 3 employing only the other species of the essential two solvents of the invention exhibited poor dispersion stability and poor resistance to ethanol and caused clogging of nozzles, thereby providing defective images.
- Ink compositions of Examples 5 to 8 and Comparative Examples 4 to 6 were prepared by kneading, by means of a sand mill for three hours, respective mixtures containing components in respective amounts (parts by mass) shown in Table 2.
- Nipex 170IQ carbon black, product of Degussa
- VYHD vinyl chloride copolymer resin, product of Dow Chemical Co.
- CAB-551-0.01 cellulose ester resin, product of Eastman
- Solsperse 32000 polyyester-polyamide resin (solid content: 100%), product of Avecia
- Disperbyk 9077 polyyester-polyamide resin (solid content: 99%), product of Byk-Chemie).
- Example 5 to 8 and Comparative Examples 4 to 6 were analyzed in terms of viscosity, particle size, dispersion stability, clogging of nozzles, and resistance to ethanol, through the following methods. These properties were evaluated according to the aforementioned ratings. The test results and evaluation are shown in Table 2.
- the ink of Comparative Example 4 employing a solvent mixture falling outside the scope of the invention caused clogging of nozzles and provided defective images.
- the ink of Comparative Example 5 employing only one species of the essential two solvents of the invention exhibited poor dispersion stability and caused clogging of nozzles, thereby providing defective images.
- the ink of Comparative Example 6 employing only the other species of the essential two solvents of the invention exhibited poor dispersion stability and poor resistance to ethanol and caused clogging of nozzles, thereby providing defective images.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Impression-Transfer Materials And Handling Thereof (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Particle Formation And Scattering Control In Inkjet Printers (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004-240014 | 2004-08-19 | ||
| JP2004240014A JP3992151B2 (ja) | 2004-08-19 | 2004-08-19 | インクジェット印刷用インク |
| JP2004-240013 | 2004-08-19 | ||
| JP2004240013A JP3992150B2 (ja) | 2004-08-19 | 2004-08-19 | インクジェット印刷用インク組成物 |
| PCT/JP2005/009080 WO2006018922A1 (ja) | 2004-08-19 | 2005-05-18 | インクジェット印刷用インク組成物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2005/009080 A-371-Of-International WO2006018922A1 (ja) | 2004-08-19 | 2005-05-18 | インクジェット印刷用インク組成物 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/836,005 Division US8586656B2 (en) | 2004-08-19 | 2010-07-14 | Ink composition for inkjet printing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20080097005A1 true US20080097005A1 (en) | 2008-04-24 |
Family
ID=35907316
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/660,445 Abandoned US20080097005A1 (en) | 2004-08-19 | 2005-05-18 | Ink Composition for Inkjet Printing |
| US12/836,005 Active 2026-01-25 US8586656B2 (en) | 2004-08-19 | 2010-07-14 | Ink composition for inkjet printing |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/836,005 Active 2026-01-25 US8586656B2 (en) | 2004-08-19 | 2010-07-14 | Ink composition for inkjet printing |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20080097005A1 (ja) |
| EP (1) | EP1783179B1 (ja) |
| KR (1) | KR100851257B1 (ja) |
| AT (1) | ATE425230T1 (ja) |
| AU (2) | AU2005273468B2 (ja) |
| BR (1) | BRPI0514358A (ja) |
| CA (1) | CA2577264C (ja) |
| DE (1) | DE602005013243D1 (ja) |
| ES (1) | ES2320153T3 (ja) |
| MX (1) | MX2007001911A (ja) |
| NZ (1) | NZ553922A (ja) |
| RU (1) | RU2342414C1 (ja) |
| WO (1) | WO2006018922A1 (ja) |
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| US20070225185A1 (en) * | 2006-03-22 | 2007-09-27 | Fujifilm Corporation | Ink washing liquid and cleaning method |
| US20080194733A1 (en) * | 2005-05-24 | 2008-08-14 | Jettable, Ltd. | Pigmented Inks Suitable For Use With Ceramics and Method of Producing Same |
| US20100028625A1 (en) * | 2008-07-31 | 2010-02-04 | Seiko Epson Corporation | Ink composition, recorded material, recording method, and recording apparatus |
| US20100126206A1 (en) * | 2008-11-26 | 2010-05-27 | Park Jeong Taek | Indoor unit for air conditioning apparatus |
| US20110021675A1 (en) * | 2008-03-24 | 2011-01-27 | Toyo Ink Manufacturing Co., Ltd. | Dispersing agent, and pigment composition, pigment-dispersed product and inkjet ink prepared therefrom |
| US8883292B2 (en) | 2008-10-22 | 2014-11-11 | Seiko Epson Corporation | Ink composition, and recorded matter, recording method and recording apparatus using the same |
| US20150147541A1 (en) * | 2012-05-30 | 2015-05-28 | S+S Patente Gmbh | Composition for printing ink and method for printing objects |
| EP2951249B1 (en) | 2013-02-01 | 2016-11-02 | Markem-Imaje Holding | Ink composition for liquid jet printing |
| US9574098B2 (en) | 2013-01-29 | 2017-02-21 | Ricoh Company, Ltd. | Ink for inkjet recording and recording method therewith |
| US9764559B2 (en) | 2006-12-19 | 2017-09-19 | Seiko Epson Corporation | Pigment dispersion, ink composition, inkset, and recording device |
| US9783689B2 (en) | 2013-10-02 | 2017-10-10 | Toyo Ink Sc Holdings Co., Ltd. | Solvent-based inkjet ink |
| US10781327B2 (en) | 2015-02-24 | 2020-09-22 | Seiko Epson Corporation | Ink jet ink composition and ink jet recording method |
| US10800162B2 (en) | 2016-01-27 | 2020-10-13 | Seiko Epson Corporation | Non-aqueous ink jet composition |
| US10919311B2 (en) | 2015-02-24 | 2021-02-16 | Seiko Epson Corporation | Ink jet ink composition, ink jet recording method, and ink set |
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| US8263682B1 (en) | 2005-11-29 | 2012-09-11 | Hilord Chemical Corporation | Solvent-based dye sublimation ink composition |
| PL2284226T3 (pl) * | 2008-03-04 | 2017-07-31 | Dai Nippon Toryo Co., Ltd. | Kompozycja niewodnego tuszu do druku atramentowego |
| US9815995B2 (en) * | 2012-02-03 | 2017-11-14 | Toyo Seikan Group Holdings, Ltd. | Ink for ink-jet printing, printed cylindrical containers and method for producing the same |
| CN108291056A (zh) | 2015-12-07 | 2018-07-17 | 醋酸纤维国际有限责任公司 | 乙酸纤维素成膜组合物 |
| US10119037B2 (en) | 2015-12-07 | 2018-11-06 | Acetate International Llp | Cellulose acetate wood filler compositions |
| WO2019139927A1 (en) | 2018-01-09 | 2019-07-18 | Acetate International Llc | Compositions and methods of 3-d printing using a cellulose ester |
| CN113993954B (zh) | 2019-04-17 | 2023-10-24 | 艾利丹尼森公司 | 快干喷墨油墨组合物 |
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- 2005-05-18 DE DE602005013243T patent/DE602005013243D1/de not_active Expired - Lifetime
- 2005-05-18 EP EP05741064A patent/EP1783179B1/en not_active Expired - Lifetime
- 2005-05-18 AU AU2005273468A patent/AU2005273468B2/en not_active Ceased
- 2005-05-18 NZ NZ553922A patent/NZ553922A/en not_active IP Right Cessation
- 2005-05-18 WO PCT/JP2005/009080 patent/WO2006018922A1/ja not_active Ceased
- 2005-05-18 US US11/660,445 patent/US20080097005A1/en not_active Abandoned
- 2005-05-18 BR BRPI0514358-6A patent/BRPI0514358A/pt not_active Application Discontinuation
- 2005-05-18 RU RU2007109811/04A patent/RU2342414C1/ru active
- 2005-05-18 KR KR1020077001833A patent/KR100851257B1/ko not_active Expired - Fee Related
- 2005-05-18 CA CA002577264A patent/CA2577264C/en not_active Expired - Lifetime
- 2005-05-18 AT AT05741064T patent/ATE425230T1/de not_active IP Right Cessation
- 2005-05-18 ES ES05741064T patent/ES2320153T3/es not_active Expired - Lifetime
- 2005-05-18 MX MX2007001911A patent/MX2007001911A/es active IP Right Grant
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- 2009-10-06 AU AU2009222563A patent/AU2009222563A1/en not_active Abandoned
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Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080194733A1 (en) * | 2005-05-24 | 2008-08-14 | Jettable, Ltd. | Pigmented Inks Suitable For Use With Ceramics and Method of Producing Same |
| US20070225185A1 (en) * | 2006-03-22 | 2007-09-27 | Fujifilm Corporation | Ink washing liquid and cleaning method |
| US9764559B2 (en) | 2006-12-19 | 2017-09-19 | Seiko Epson Corporation | Pigment dispersion, ink composition, inkset, and recording device |
| US10780707B2 (en) | 2006-12-19 | 2020-09-22 | Seiko Epson Corporation | Pigment dispersion, ink composition, inkset, and recording device |
| US10486433B2 (en) | 2006-12-19 | 2019-11-26 | Seiko Epson Corporation | Pigment dispersion, ink composition, inkset, and recording device |
| US10059121B2 (en) | 2006-12-19 | 2018-08-28 | Seiko Epson Corporation | Pigment dispersion, ink composition, inkset, and recording device |
| US20110021675A1 (en) * | 2008-03-24 | 2011-01-27 | Toyo Ink Manufacturing Co., Ltd. | Dispersing agent, and pigment composition, pigment-dispersed product and inkjet ink prepared therefrom |
| US8344047B2 (en) | 2008-03-24 | 2013-01-01 | Toyo Ink Manufacturing Co., Ltd. | Dispersing agent, and pigment composition, pigment-dispersed product and inkjet ink prepared therefrom |
| US20100028625A1 (en) * | 2008-07-31 | 2010-02-04 | Seiko Epson Corporation | Ink composition, recorded material, recording method, and recording apparatus |
| US8158697B2 (en) | 2008-07-31 | 2012-04-17 | Seiko Epson Corporation | Ink composition, recorded material, recording method, and recording apparatus |
| US9862850B2 (en) | 2008-10-22 | 2018-01-09 | Seiko Epson Corporation | Ink composition, and recorded matter, recording method and recording apparatus using the same |
| US9090792B2 (en) | 2008-10-22 | 2015-07-28 | Seiko Epson Corporation | Ink composition, and recorded matter, recording method and recording apparatus using the same |
| US8883292B2 (en) | 2008-10-22 | 2014-11-11 | Seiko Epson Corporation | Ink composition, and recorded matter, recording method and recording apparatus using the same |
| US20100126206A1 (en) * | 2008-11-26 | 2010-05-27 | Park Jeong Taek | Indoor unit for air conditioning apparatus |
| US20150147541A1 (en) * | 2012-05-30 | 2015-05-28 | S+S Patente Gmbh | Composition for printing ink and method for printing objects |
| US9574098B2 (en) | 2013-01-29 | 2017-02-21 | Ricoh Company, Ltd. | Ink for inkjet recording and recording method therewith |
| EP2951249B1 (en) | 2013-02-01 | 2016-11-02 | Markem-Imaje Holding | Ink composition for liquid jet printing |
| US9850392B2 (en) * | 2013-02-01 | 2017-12-26 | Markem-Imaje Holding | Ink composition for liquid jet printing |
| US9783689B2 (en) | 2013-10-02 | 2017-10-10 | Toyo Ink Sc Holdings Co., Ltd. | Solvent-based inkjet ink |
| US10781327B2 (en) | 2015-02-24 | 2020-09-22 | Seiko Epson Corporation | Ink jet ink composition and ink jet recording method |
| US10919311B2 (en) | 2015-02-24 | 2021-02-16 | Seiko Epson Corporation | Ink jet ink composition, ink jet recording method, and ink set |
| US11718100B2 (en) | 2015-02-24 | 2023-08-08 | Seiko Epson Corporation | Ink jet ink composition, ink jet recording method, and ink set |
| US10800162B2 (en) | 2016-01-27 | 2020-10-13 | Seiko Epson Corporation | Non-aqueous ink jet composition |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2320153T3 (es) | 2009-05-19 |
| EP1783179B1 (en) | 2009-03-11 |
| MX2007001911A (es) | 2007-05-09 |
| RU2342414C1 (ru) | 2008-12-27 |
| EP1783179A1 (en) | 2007-05-09 |
| NZ553922A (en) | 2009-10-30 |
| BRPI0514358A (pt) | 2008-06-10 |
| EP1783179A4 (en) | 2007-09-05 |
| CA2577264A1 (en) | 2006-02-23 |
| US20100280158A1 (en) | 2010-11-04 |
| CA2577264C (en) | 2009-09-15 |
| US8586656B2 (en) | 2013-11-19 |
| DE602005013243D1 (de) | 2009-04-23 |
| RU2007109811A (ru) | 2008-09-27 |
| WO2006018922A1 (ja) | 2006-02-23 |
| KR20070037497A (ko) | 2007-04-04 |
| AU2005273468B2 (en) | 2009-10-29 |
| KR100851257B1 (ko) | 2008-08-08 |
| AU2009222563A1 (en) | 2009-10-22 |
| AU2005273468A1 (en) | 2006-02-23 |
| ATE425230T1 (de) | 2009-03-15 |
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