JP2006016458A - Pigment ink composition for inkjet - Google Patents
Pigment ink composition for inkjet Download PDFInfo
- Publication number
- JP2006016458A JP2006016458A JP2004194114A JP2004194114A JP2006016458A JP 2006016458 A JP2006016458 A JP 2006016458A JP 2004194114 A JP2004194114 A JP 2004194114A JP 2004194114 A JP2004194114 A JP 2004194114A JP 2006016458 A JP2006016458 A JP 2006016458A
- Authority
- JP
- Japan
- Prior art keywords
- ink composition
- water
- acid
- ink
- meth
- 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
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 239000000049 pigment Substances 0.000 title claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 239000003086 colorant Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 31
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000011347 resin Substances 0.000 claims abstract description 21
- 229920005989 resin Polymers 0.000 claims abstract description 21
- 239000011248 coating agent Substances 0.000 claims abstract description 9
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 150000002429 hydrazines Chemical class 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide group Chemical group NNC(=O)N DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 2
- 238000005299 abrasion Methods 0.000 abstract description 15
- 239000002932 luster Substances 0.000 abstract 1
- 238000001454 recorded image Methods 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 90
- -1 acryl Chemical group 0.000 description 61
- 238000002360 preparation method Methods 0.000 description 33
- 239000006185 dispersion Substances 0.000 description 25
- 239000000178 monomer Substances 0.000 description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000002245 particle Substances 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012860 organic pigment Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 239000004952 Polyamide Substances 0.000 description 7
- 229920001214 Polysorbate 60 Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003125 aqueous solvent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical group OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920006317 cationic polymer Polymers 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000005056 polyisocyanate Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 5
- 229920002451 polyvinyl alcohol Polymers 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical group FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 239000001530 fumaric acid Chemical group 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Chemical group 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Chemical group OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 230000037303 wrinkles Effects 0.000 description 3
- BXALRZFQYDYTGH-UHFFFAOYSA-N 1-oxoprop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)C(=O)C=C BXALRZFQYDYTGH-UHFFFAOYSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 2
- RTTAGBVNSDJDTE-UHFFFAOYSA-N 4-ethoxy-2-methylidene-4-oxobutanoic acid Chemical compound CCOC(=O)CC(=C)C(O)=O RTTAGBVNSDJDTE-UHFFFAOYSA-N 0.000 description 2
- OIYTYGOUZOARSH-UHFFFAOYSA-N 4-methoxy-2-methylidene-4-oxobutanoic acid Chemical compound COC(=O)CC(=C)C(O)=O OIYTYGOUZOARSH-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229920006318 anionic polymer Polymers 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical group C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 239000004584 polyacrylic acid Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003349 semicarbazides Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Chemical group CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 2
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- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- ZZSIDSMUTXFKNS-UHFFFAOYSA-N perylene red Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N(C(=O)C=1C2=C3C4=C(OC=5C=CC=CC=5)C=1)C(=O)C2=CC(OC=1C=CC=CC=1)=C3C(C(OC=1C=CC=CC=1)=CC1=C2C(C(N(C=3C(=CC=CC=3C(C)C)C(C)C)C1=O)=O)=C1)=C2C4=C1OC1=CC=CC=C1 ZZSIDSMUTXFKNS-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229940096992 potassium oleate Drugs 0.000 description 1
- MLICVSDCCDDWMD-KVVVOXFISA-M potassium;(z)-octadec-9-enoate Chemical compound [K+].CCCCCCCC\C=C/CCCCCCCC([O-])=O MLICVSDCCDDWMD-KVVVOXFISA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- ZIWRUEGECALFST-UHFFFAOYSA-M sodium 4-(4-dodecoxysulfonylphenoxy)benzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCOS(=O)(=O)c1ccc(Oc2ccc(cc2)S([O-])(=O)=O)cc1 ZIWRUEGECALFST-UHFFFAOYSA-M 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940079839 sodium dehydroacetate Drugs 0.000 description 1
- 235000019259 sodium dehydroacetate Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- UGJCNRLBGKEGEH-UHFFFAOYSA-N sodium-binding benzofuran isophthalate Chemical compound COC1=CC=2C=C(C=3C(=CC(=CC=3)C(O)=O)C(O)=O)OC=2C=C1N(CCOCC1)CCOCCOCCN1C(C(=CC=1C=2)OC)=CC=1OC=2C1=CC=C(C(O)=O)C=C1C(O)=O UGJCNRLBGKEGEH-UHFFFAOYSA-N 0.000 description 1
- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- HLWRUJAIJJEZDL-UHFFFAOYSA-M sodium;2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [Na+].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC([O-])=O HLWRUJAIJJEZDL-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- JSMHQMIPUOPQLR-UHFFFAOYSA-M sodium;dioctadecyl phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCCCCCCCC JSMHQMIPUOPQLR-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Description
本発明は水系顔料インクを用いた記録、印刷を行うにおいて、高い耐擦性が得られ、且つ光沢むらが生じにくいインク組成物に関する。 The present invention relates to an ink composition that provides high abrasion resistance and is less likely to cause gloss unevenness in recording and printing using a water-based pigment ink.
インクジェット記録用インクは大別すると油性インクと水性インクがあるが、油性インクは臭気・毒性の点で問題があり、水性インクが主流となりつつある。しかしながら、従来の水性インクの多くは着色剤として水溶性染料を用いているため耐水性や耐光性が悪いという欠点を有していた。
上記欠点を改良するためにいわゆる水性の顔料インクが過去に様々に提案されているが、これらは得られる画像の耐擦性が低く、さらに平滑性が高い記録媒体を使用した際には画像の耐擦性の低さが顕著な欠点となっていた。
そこで、これら欠点を改良する方法として、例えば、顔料（水系溶媒に不溶性の着色剤）を接着させるポリマーラテックスを含有するインク組成物あるいはマイクロカプセルとして顔料を内包するインク組成物などが各種提案されている。
Ink jet recording inks are roughly classified into oil-based inks and water-based inks, but oil-based inks have problems in terms of odor and toxicity, and water-based inks are becoming mainstream. However, many of the conventional water-based inks have a drawback that water resistance and light resistance are poor because a water-soluble dye is used as a colorant.
Various so-called water-based pigment inks have been proposed in the past in order to improve the above-mentioned drawbacks. However, these images have low abrasion resistance of the obtained image, and when using a recording medium having high smoothness, Low rub resistance was a significant drawback.
Therefore, as a method for improving these defects, for example, various ink compositions containing a polymer latex for adhering a pigment (colorant insoluble in an aqueous solvent) or an ink composition containing a pigment as a microcapsule have been proposed. Yes.
具体的には、特許文献１では、インク成分としての顔料、水溶性もしくは水分散性ポリエステル又はポリアミドからなるバインダー成分、トリアジン環含有化合物又はエポキシ化合物からなる架橋剤成分、及び水を含有することを特徴とするインクジェット用インク組成物が、特許文献２では水溶性染料、水性媒体並びに水溶性ポリアミドを含有する記録液が、特許文献３では水溶性染料、水性媒体、強塩基性化合物並びに水可溶性樹脂を含有することを特徴とする記録液のうち水可溶性樹脂として水溶性ポリアミドが、特許文献４では水、着色剤、水溶性のアニオン性重合体及び水溶性のカチオン重合体を含有することを特徴とする水性インク組成物において水溶性のカチオン重合体としてポリアミド−エピクロルヒドリン樹脂が、特許文献５では、着色剤、該着色剤を用紙に固着させる結合剤、および着色剤及び結合剤を分散させる溶剤からなるインクジェットプリンター用の液体インキにおいて、インキ総量の１０〜９０質量％の水を含み、結合剤がポリアミドカルボン酸塩からなることを特徴とする液体インキと、その液体インキを用いたことを特徴とするインクジェットプリンターと、用紙に形成された画像を加熱してポリアミドカルボン酸塩をポリイミドに変化させる定着処理を行うことを特徴とする画像形成方法が、特許文献６では、少なくとも、水、蒸気圧が水よりも小さい水溶性有機溶剤、この水溶性有機溶剤に可溶な油溶性染料、分散染料、顔料から選ばれる少なくともひとつの疎水性着色剤、前記水溶性有機溶剤に可溶な疎水性樹脂からなり、この疎水性樹脂としてポリアミドを使用し、インク中でこの疎水性樹脂の分散状態が存在していることを特徴とする水性分散インクが、さらに、例えは特許文献７あるいは特許文献８などにおいては着色剤として、顔料を樹脂で被覆したマイクロカプセル化顔料を含有する水性インク組成物等が提案されている。 Specifically, Patent Document 1 contains a pigment as an ink component, a binder component made of water-soluble or water-dispersible polyester or polyamide, a crosslinking agent component made of a triazine ring-containing compound or an epoxy compound, and water. The ink-jet ink composition is characterized in that Patent Document 2 discloses a recording liquid containing a water-soluble dye, an aqueous medium and a water-soluble polyamide, and Patent Document 3 discloses a water-soluble dye, an aqueous medium, a strongly basic compound and a water-soluble resin. Among the recording liquids containing water, a water-soluble polyamide is used as a water-soluble resin, and Patent Document 4 contains water, a colorant, a water-soluble anionic polymer, and a water-soluble cationic polymer. Polyamide-epichlorohydrin resin as a water-soluble cationic polymer in the aqueous ink composition 5, the liquid ink for an ink jet printer comprising a colorant, a binder for fixing the colorant to the paper, and a solvent for dispersing the colorant and the binder, containing 10 to 90% by mass of water based on the total amount of the ink; A liquid ink characterized in that the binder is composed of polyamide carboxylate, an ink jet printer characterized by using the liquid ink, and an image formed on the paper is heated to convert the polyamide carboxylate into polyimide. An image forming method characterized by performing a fixing process to be changed is disclosed in Patent Document 6, in which at least water, a water-soluble organic solvent having a vapor pressure lower than water, an oil-soluble dye soluble in the water-soluble organic solvent, The hydrophobic resin comprises at least one hydrophobic colorant selected from disperse dyes and pigments, and a hydrophobic resin soluble in the water-soluble organic solvent. A water-based dispersion ink characterized in that a dispersion state of the hydrophobic resin is present in the ink. Further, for example, in Patent Document 7 or Patent Document 8, a pigment is used as a colorant. A water-based ink composition containing a microencapsulated pigment coated with a resin has been proposed.
しかしながら、特許文献１では顔料の分散安定性や架橋剤成分を含有することによるインクの安定性に問題があり、特許文献２及び特許文献３では水溶性染料を使用しているために耐水性や耐光性の問題に加えて、滲み改良効果が少ないという問題があり、特許文献４のアニオン性重合体及び水溶性のカチオン重合体を含有するインクはインクの安定性のｐＨ依存性が大きいという問題があり、特許文献５では用紙に形成された画像を加熱してインク中のポリアミドカルボン酸塩をポリイミドに変化させる定着処理が必要であるという問題があり、特許文献６では疎水性樹脂（ポリアミド）がインク中において分散状態で存在するのでインクの分散安定性や吐出安定性に問題があり、特許文献７および特許文献８などにおいては満足のいく画像が得られないなどの問題があった。 However, in Patent Document 1, there is a problem in the dispersion stability of the pigment and the stability of the ink due to the inclusion of the crosslinking agent component, and in Patent Document 2 and Patent Document 3, since water-soluble dyes are used, In addition to the problem of light resistance, there is a problem that the effect of improving bleeding is small, and the ink containing the anionic polymer and the water-soluble cationic polymer of Patent Document 4 has a problem that the pH stability of the ink stability is large. In Patent Document 5, there is a problem that a fixing process is required in which an image formed on a sheet is heated to change the polyamide carboxylate in the ink to polyimide. In Patent Document 6, a hydrophobic resin (polyamide) is required. Is present in a dispersed state in the ink, so there is a problem in the dispersion stability and ejection stability of the ink. In Patent Document 7 and Patent Document 8, satisfactory images are obtained. There was a problem, such as not be obtained.
さらに、近年、銀塩写真並の高画質を得るためのインクジェット記録媒体の技術開発が進み、ポリオレフィンで被覆した紙やポリマーフィルムなどの平滑性の高い支持体上に、無機微粒子により形成される微小空隙を有するインク吸収層を設けた高光沢記録媒体が、写真画質に迫るものとして市販されている。しかしながら、このような高光沢記録媒体に顔料インクを用いて印刷（記録）を行った場合、画像部分（インクが乗っている部分）の光沢感が低く、白紙部分（インクが乗っていない記録媒体の部分）との光沢感との相違が生じるという問題が生じていた。
本発明は、従来技術では困難であった、高い耐擦性が得られ、且つ光沢むらが生じにくい優れた記録物を得ることが可能なインク組成物および記録方法を提供することを目的課題とする。 SUMMARY OF THE INVENTION An object of the present invention is to provide an ink composition and a recording method capable of obtaining an excellent recorded matter that has high abrasion resistance and is less likely to cause uneven glossiness, which has been difficult in the prior art. To do.
本発明者等は、前記課題を解決するために鋭意検討した結果、着色剤と水とを少なくとも含んでなるインクジェット用インク組成物であって、前記着色剤が顔料を樹脂により被覆してなるものであり、前記樹脂がＮ置換（メタ）アクリルアミド単位を含有してなる高分子化合物（Ａ）であることを特徴とする前記インク組成物を使用して記録を行うことが前記課題の解決に有効であることを見出し、本発明をなすに至った。 As a result of intensive studies to solve the above-mentioned problems, the present inventors are an ink-jet ink composition comprising at least a colorant and water, wherein the colorant is obtained by coating a pigment with a resin. In order to solve the above problem, it is effective to perform recording using the ink composition, wherein the resin is a polymer compound (A) containing an N-substituted (meth) acrylamide unit. As a result, the present invention has been made.
すなわち、本発明は以下の通りである。
１） 着色剤と水とを少なくとも含んでなるインクジェット用インク組成物であって、前記着色剤が顔料を樹脂により被覆してなるものであり、前記樹脂がＮ置換（メタ）アクリルアミド単位を含有してなる高分子化合物（Ａ）であることを特徴とする前記インク組成物。
２） 前記高分子化合物（Ａ）が、カルボニル基を有する高分子化合物と、少なくとも２個の、ヒドラジン基及び／又はセミカルバジド基を有するヒドラジン誘導体とを含有することを特徴とする１）の発明のインク組成物。
３） インク組成物の液滴を吐出し、該液滴を記録媒体に付着させて印刷を行うインクジェット記録方法において、インク組成物として１）または２）の発明のインク組成物を用いることを特徴とする記録方法によって記録が行われた記録物。
That is, the present invention is as follows.
1) An ink-jet ink composition comprising at least a colorant and water, wherein the colorant is obtained by coating a pigment with a resin, and the resin contains an N-substituted (meth) acrylamide unit. The ink composition, which is a polymer compound (A).
2) According to the invention of 1), the polymer compound (A) comprises a polymer compound having a carbonyl group and at least two hydrazine derivatives having a hydrazine group and / or a semicarbazide group. Ink composition.
3) In an ink jet recording method in which a droplet of an ink composition is ejected and printing is performed by attaching the droplet to a recording medium, the ink composition of 1) or 2) of the invention is used as the ink composition. Recorded material recorded by the recording method.
本発明のインク組成物および記録方法を用いれば、従来技術では困難であった、高い耐擦性が得られ、且つ光沢むらが生じにくい優れた記録物を得ることが可能になり、産業上の利用価値は甚だ大きなものである。 By using the ink composition and the recording method of the present invention, it is possible to obtain an excellent recorded matter that has high abrasion resistance and is less likely to cause uneven glossiness, which has been difficult in the prior art. The utility value is very large.
本発明について、以下に具体的に説明する。
本発明のインク組成物に用いることのできる顔料としては、有機顔料および無機顔料ともに用いることが出来るが、例えば粒子径の小さな各種の有機顔料やカーボンブラックが特に有効に用いられる。高品質の画像が得られるという観点から、一次粒子に小さな顔料を用いることが好ましく、透過型電子顕微鏡を用いて測定した顔料の一次粒子の平均粒径が１０〜１００ｎｍであることが好ましく、さらには１０〜５０ｎｍであることが好ましい。
有機顔料としては、キナクリドン系有機顔料、フタロシアニン系有機顔料、アゾ系有機顔料、イソインドリノン系有機顔料、イミダゾロン系有機顔料からなる群より選ばれる１種ないし２種以上が好適に用いられる。
The present invention will be specifically described below.
As the pigment that can be used in the ink composition of the present invention, both organic pigments and inorganic pigments can be used. For example, various organic pigments having a small particle diameter and carbon black are particularly effectively used. From the viewpoint that a high-quality image can be obtained, it is preferable to use a small pigment for the primary particles, and the average particle size of the primary particles of the pigment measured using a transmission electron microscope is preferably 10 to 100 nm. Is preferably 10 to 50 nm.
As the organic pigment, one or more selected from the group consisting of quinacridone organic pigments, phthalocyanine organic pigments, azo organic pigments, isoindolinone organic pigments, and imidazolone organic pigments are preferably used.
有機顔料として具体的には、トルイジンレッド、トルイジンマルーン、ハンザエロー、ベンジジンエロー、ピラゾロンレッドなどの不溶性アゾ顔料、リトールレッド、ヘリオボルドー、ピグメントスカーレット、パーマネントレッド２Ｂなどの溶性アゾ顔料、アリザリン、インダントロン、チオインジゴマルーンなどの建染染料からの誘導体、フタロシアニンブルー、フタロシアニングリーンなどのフタロシアニン系顔料、キナクリドンレッド、キナクリドンマゼンタなどのキナクリドン系顔料、ペリレンレッド、ペリレンスカーレットなどのペリレン系顔料、イソインドリノンエロー、イソインドリノンオレンジなどのイソインドリノン系顔料、ベンズイミダゾロンエロー、ベンズイミダゾロンオレンジ、ベンズイミダゾロンレッド等のイミダゾロン系顔料、ピランスロンレッド、ピランスロンオレンジなどのピランスロン系顔料、チオインジゴ系顔料、縮合アゾ系顔料、チオインジゴ系顔料、フラバンスロンエロー、アシルアミドエロー、キノフタロンエロー、ニッケルアゾエロー、銅アゾメチンエロー、ペリノンオレンジ、アンスロンオレンジ、ジアンスラキノニルレッド、ジオキサジンバイオレット等のその他の顔料が例示できる。 Specific examples of organic pigments include insoluble azo pigments such as toluidine red, toluidine maroon, Hansa Yellow, Benzidine Yellow, and pyrazolone red, soluble azo pigments such as Ritolol Red, Helio Bordeaux, Pigment Scarlet, and Permanent Red 2B, Alizarin, Indantron Derivatives from vat dyes such as thioindigo maroon, phthalocyanine pigments such as phthalocyanine blue and phthalocyanine green, quinacridone pigments such as quinacridone red and quinacridone magenta, perylene pigments such as perylene red and perylene scarlet, isoindolinone yellow , Isoindolinone pigments such as isoindolinone orange, benzimidazolone yellow, benzimidazolone orange, benzimidazolone red, etc. Dazolone pigments, pyranthrone pigments such as pyranthrone red, pyranthrone orange, thioindigo pigments, condensed azo pigments, thioindigo pigments, flavanthlon yellow, acylamide yellow, quinophthalone yellow, nickel azo yellow, copper azomethine yellow, peri Other pigments such as non-orange, anthrone orange, dianthraquinonyl red, dioxazine violet can be exemplified.
また、有機顔料をカラーインデックス（Ｃ．Ｉ．）ナンバーにて示すと、Ｃ．Ｉ．ピグメントエロー１２、１３、１４、１７、２０、２４、７４、８３、８６９３、１０９、１１０、１１７、１２０、１２５、１３７、１３８、１４７、１４８、１５１、１５３、１５４、１６６、１６８、Ｃ．Ｉ．ピグメントオレンジ１６、３６、４３、５１、５５、５９、６１、Ｃ．Ｉ．ピグメントレッド９、４８、４９、５２、５３、５７、９７、１２２、１２３、１４９、１６８、１７５、１７６、１７７、１８０、１９２、２１５、２１６、２１７、２２０、２２３、２２４、２２６、２２７、２２８、２３８、２４０、Ｃ．Ｉ．ピグメントバイオレット１９、２３、２９、３０、３７、４０、５０、Ｃ．Ｉ．ピグメントブルー１５、１５：１、１５：４、１５：６、２２、６０、６４、Ｃ．Ｉ．ピグメントグリーン７、３６、Ｃ．Ｉ．ピグメントブラウン２３、２５、２６等が例示できる。 Further, when the organic pigment is represented by a color index (CI) number, C.I. I. Pigment Yellow 12, 13, 14, 17, 20, 24, 74, 83, 8893, 109, 110, 117, 120, 125, 137, 138, 147, 148, 151, 153, 154, 166, 168, C.I. I. Pigment orange 16, 36, 43, 51, 55, 59, 61, C.I. I. Pigment Red 9, 48, 49, 52, 53, 57, 97, 122, 123, 149, 168, 175, 176, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, 238, 240, C.I. I. Pigment violet 19, 23, 29, 30, 37, 40, 50, C.I. I. Pigment blue 15, 15: 1, 15: 4, 15: 6, 22, 60, 64, C.I. I. Pigment green 7, 36, C.I. I. Examples thereof include CI Pigment Brown 23, 25, 26, and the like.
本発明の高分子化合物（Ａ）はＮ置換（メタ）アクリルアミドモノマー（以下、主モノマー（Ｂ）という。）の単独重合高分子化合物、または二種類以上の主モノマー（Ｂ）の共重合高分子化合物、さらには、該主モノマー（Ｂ）と反応して高分子化合物（Ａ）を作ることができるＮ置換（メタ）アクリルアミドモノマーに該当しないモノマー（以下、副モノマー（Ｃ）という。）と主モノマー（Ｂ）との共重合高分子化合物である。主モノマー（Ｂ）と副モノマー（Ｃ）は各々１種または２種以上のものを組み合わせて用いることも出来る。 The polymer compound (A) of the present invention is a homopolymer polymer compound of N-substituted (meth) acrylamide monomer (hereinafter referred to as main monomer (B)) or a copolymer polymer of two or more kinds of main monomers (B). The main component (B) is a compound that does not correspond to an N-substituted (meth) acrylamide monomer that can react with the main monomer (B) to form a polymer compound (A) (hereinafter referred to as submonomer (C)). It is a copolymerized polymer compound with the monomer (B). The main monomer (B) and the submonomer (C) can be used alone or in combination of two or more.
主モノマー（Ｂ）としてはＮ−アルキルまたはＮ−アルキレン置換（メタ）アクリルアミド誘導体（ここで、（メタ）アクリルとはメタアクリル（またはメタクリル）またはアクリルを簡便に表記したものである）などが挙げられ、具体的には例えば、Ｎ−エチル（メタ）アクリルアミド、Ｎ−イソプロピル（メタ）アクリルアミド、Ｎ−シクロプロピル（メタ）アクリルアミド、Ｎ−エチル（メタ）アクリルアミド、Ｎ，Ｎ−ジエチル（メタ）アクリルアミド、Ｎ，Ｎ−ジメチル（メタ）アクリルアミド、Ｎ−ｎ−プロピル（メタ）アクリルアミド、Ｎ−メチル−Ｎ−ｎ−プロピルアクリルアミド、Ｎ−メチル−Ｎ−イソプロピルアクリルアミド、Ｎ−（メタ）アクリロイルピロリジン、Ｎ−（メタ）アクリロイルピペリジン、Ｎ−テトラヒドロフルフリル（メタ）アクリルアミド、Ｎ−メトキシプロピル（メタ）アクリルアミド、Ｎ−エトキシプロピル（メタ）アクリルアミド、Ｎ−イソプロポキシプロピル（メタ）アクリルアミド、Ｎ−エトキシエチル（メタ）アクリルアミド、Ｎ−（２，２−ジメトキシエチル）−Ｎ−メチルアクリルアミド、Ｎ−メトキシエチル（メタ）アクリルアミドなどが挙げられる。得られる画像の耐擦性の観点から、Ｎ−イソプロピルアクリルアミド、Ｎ−ｎ−プロピルアクリルアミド、Ｎ，Ｎ−ジエチルアクリルアミド、Ｎ，Ｎ−ジメチル（メタ）アクリルアミドが好ましい。 Examples of the main monomer (B) include N-alkyl or N-alkylene-substituted (meth) acrylamide derivatives (where (meth) acryl is a simple representation of methacryl (or methacryl) or acryl). Specifically, for example, N-ethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-cyclopropyl (meth) acrylamide, N-ethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide N, N-dimethyl (meth) acrylamide, Nn-propyl (meth) acrylamide, N-methyl-Nn-propylacrylamide, N-methyl-N-isopropylacrylamide, N- (meth) acryloylpyrrolidine, N -(Meth) acryloylpiperidine, N-tetra Drofurfuryl (meth) acrylamide, N-methoxypropyl (meth) acrylamide, N-ethoxypropyl (meth) acrylamide, N-isopropoxypropyl (meth) acrylamide, N-ethoxyethyl (meth) acrylamide, N- (2,2- And dimethoxyethyl) -N-methylacrylamide, N-methoxyethyl (meth) acrylamide and the like. From the viewpoint of the abrasion resistance of the obtained image, N-isopropylacrylamide, Nn-propylacrylamide, N, N-diethylacrylamide, and N, N-dimethyl (meth) acrylamide are preferable.
副モノマー（Ｃ）としては親油性ビニル化合物、親水性ビニル化合物、イオン性ビニル化合物などが挙げられ、具体的には、親油性ビニル化合物としては、例えばメチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、グリシジルメタクリレート、スチレン、α−メチルスチレン、エチレン、イソプレン、ブタジエン、酢酸ビニル、塩化ビニルなどが挙げられ、親水性ビニル化合物としては、例えば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、（メタ）アクリルアミド、ダイアセトンアクリルアミド、メチレンビスアクリルアミド、２−メチル−５−ビニルピリジン、Ｎ−ビニル−２−ピロリドン、Ｎ−アクリロイルピロリジン、アクリロニトリル、などが挙げられ、 Examples of the auxiliary monomer (C) include a lipophilic vinyl compound, a hydrophilic vinyl compound, and an ionic vinyl compound. Specific examples of the lipophilic vinyl compound include methyl (meth) acrylate and ethyl (meth) acrylate. , N-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, glycidyl methacrylate, styrene, α-methylstyrene, ethylene, isoprene, butadiene, vinyl acetate, vinyl chloride, and the like. As the hydrophilic vinyl compound, For example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, (meth) acrylamide, diacetone acrylamide, methylene bisacrylamide, 2-methyl-5-vinylpyridine, N-vinyl-2-pyrrolidone, N − Methacryloyl pyrrolidine, acrylonitrile, and the like,
イオン性ビニル化合物としては、例えばアクリル酸、メタクリル酸、イタコン酸、フマル酸、マレイン酸、クロトン酸、ブテントリカルボン酸、マレイン酸モノエチル、マレイン酸モノメチル、イタコン酸モノエチル、イタコン酸モノメチル等のカルボン酸基含有モノマー、２−アクリルアミド−２−メチル−プロパンスルホン酸、スチレンスルホン酸、ビニルスルホン酸、（メタ）アクリルスルホン酸等のスルホン酸基含有モノマー、Ｎ，Ｎ−ジメチルアミノエチル（メタ）アクリレート、Ｎ，Ｎ−ジエチルアミノエチル（メタ）アクリレート等のアミノ基含有モノマーなどが挙げられる。特に、メチル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、スチレン、２−ヒドロキシプロピル（メタ）アクリレート、アクリルアミド、メタアクリルアミド、ダイアセトンアクリルアミド、メチレンビスアクリルアミドが好ましく用いられる。 Examples of the ionic vinyl compound include carboxylic acid groups such as acrylic acid, methacrylic acid, itaconic acid, fumaric acid, maleic acid, crotonic acid, butenetricarboxylic acid, monoethyl maleate, monomethyl maleate, monoethyl itaconate and monomethyl itaconate. Containing monomer, 2-acrylamido-2-methyl-propanesulfonic acid, styrenesulfonic acid, vinylsulfonic acid, sulfonic acid group-containing monomer such as (meth) acrylsulfonic acid, N, N-dimethylaminoethyl (meth) acrylate, N And amino group-containing monomers such as N-diethylaminoethyl (meth) acrylate. In particular, methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, styrene, 2-hydroxypropyl (meth) acrylate, acrylamide, methacrylamide, diacetone acrylamide, and methylene bisacrylamide are preferably used. It is done.
また、インク組成物中における着色剤の分散安定性の観点から、アクリル酸、メタクリル酸、イタコン酸、フマル酸、マレイン酸、クロトン酸、ブテントリカルボン酸、マレイン酸モノエチル、マレイン酸モノメチル、イタコン酸モノエチル、イタコン酸モノメチル等のカルボン酸基含有モノマー、２−アクリルアミド−２−メチル−プロパンスルホン酸、スチレンスルホン酸、ビニルスルホン酸、（メタ）アクリルスルホン酸等のスルホン酸基含有モノマーなどのアニオン基含有モノマーを用いることは好ましく、特にアクリル酸、メタクリル酸、イタコン酸、フマル酸、マレイン酸等のカルボン酸基含有モノマーを用いることは好ましい。 Further, from the viewpoint of the dispersion stability of the colorant in the ink composition, acrylic acid, methacrylic acid, itaconic acid, fumaric acid, maleic acid, crotonic acid, butenetricarboxylic acid, monoethyl maleate, monomethyl maleate, monoethyl itaconate , Carboxylic acid group-containing monomers such as monomethyl itaconate, anionic groups such as 2-acrylamido-2-methyl-propanesulfonic acid, styrene sulfonic acid, vinyl sulfonic acid, sulfonic acid group-containing monomers such as (meth) acrylsulfonic acid It is preferable to use a monomer, and it is particularly preferable to use a carboxylic acid group-containing monomer such as acrylic acid, methacrylic acid, itaconic acid, fumaric acid and maleic acid.
主モノマー（Ｂ）と副モノマー（Ｃ）の共重合割合は用いるモノマー種の組み合わせに依存するが、得られる画像の耐擦性の観点店から、高分子化合物（Ａ）中における副モノマー（Ｃ）の割合は５０質量％以下が好ましい。更に好ましくは、３０質量％以下である。
本発明で使用する高分子化合物（Ａ）がカルボニル基を含有することは、後述のヒドラジン誘導体による架橋により、得られる画像の耐擦性が大きく向上することから特に好ましい。
カルボニル基を含有する高分子化合物（Ａ）は、例えば、カルボニル基を含有するモノマーを副モノマー（Ｃ）として使用し、主モノマー（Ｂ）および他の副モノマー（Ｃ）と共重合させて得られる高分子化合物が挙げられる。
Although the copolymerization ratio of the main monomer (B) and the submonomer (C) depends on the combination of the monomer species used, the submonomer (C) in the polymer compound (A) is selected from the viewpoint of the abrasion resistance of the obtained image. ) Is preferably 50% by mass or less. More preferably, it is 30 mass% or less.
It is particularly preferable that the polymer compound (A) used in the present invention contains a carbonyl group since the abrasion resistance of the obtained image is greatly improved by crosslinking with a hydrazine derivative described later.
The polymer compound (A) containing a carbonyl group is obtained, for example, by using a monomer containing a carbonyl group as a submonomer (C) and copolymerizing it with the main monomer (B) and another submonomer (C). The high molecular compound which can be mentioned is mentioned.
カルボニル基含有モノマーとしては、モノマー中にケト基またはアルド基を含む構造を有するもので有れば良いが、例えばアクロレイン、ダイアセトンアクリルアミド、ダイアセトンメタクリルアミド、ホルミルスチロール、ビニルメチルケトン、ビニルエチルケトン、ビニルイソブチルケトン、アクリルオキシアルキルプロパナール類、メタクリルオキシアルキルプロパナール類、ダイアセトンアクリレート、ダイアセトンメタクリレート、アセトニトリルアクリレート、２−ヒドロキシプロピルアクリレートアセチルアセテート、ブタンジオールアクリレートアセチルアセテート等が例示される。
高分子化合物（Ａ）の全モノマー単位中のカルボニル基含有モノマー単位の含有率は、耐水性付与、耐擦性付与の観点から０．０１〜３０質量％が好ましく、更に好ましくは０．１〜２０質量％である。
The carbonyl group-containing monomer may have a structure containing a keto group or an aldo group in the monomer. For example, acrolein, diacetone acrylamide, diacetone methacrylamide, formylstyrene, vinyl methyl ketone, vinyl ethyl ketone And vinyl isobutyl ketone, acryloxyalkylpropanals, methacryloxyalkylpropanals, diacetone acrylate, diacetone methacrylate, acetonitrile acrylate, 2-hydroxypropyl acrylate acetyl acetate, butanediol acrylate acetyl acetate and the like.
The content of the carbonyl group-containing monomer unit in all monomer units of the polymer compound (A) is preferably from 0.01 to 30% by mass, more preferably from 0.1 to 30% by mass from the viewpoint of imparting water resistance and abrasion resistance. 20% by mass.
本発明の高分子化合物（Ａ）がカルボニル基を含有する場合、インク受容層中に、架橋剤として少なくとも２個のヒドラジン基及び／またはセミカルバジド基を有するヒドラジン誘導体を用いることが、得られる画像の耐水性や耐擦性などの観点から好ましい。
該ヒドラジン誘導体は水の共存下ではカルボニル基との結合は進行しないが、乾燥によって脱水反応を生じ、結合を生じることが知られており、該ヒドラジン誘導体を、本発明のインク組成物に含有させることは好ましい。即ち、印刷を行った後、インク組成物が乾燥することによりカルボニル基部位がヒドラジン誘導体によって架橋された分子構造を形成することによって耐水性と耐擦性を発現する事が可能となる。
When the polymer compound (A) of the present invention contains a carbonyl group, the use of a hydrazine derivative having at least two hydrazine groups and / or semicarbazide groups as a crosslinking agent in the ink receiving layer It is preferable from the viewpoint of water resistance and abrasion resistance.
The hydrazine derivative does not proceed to bond with the carbonyl group in the presence of water, but is known to cause a dehydration reaction upon drying to form a bond. The hydrazine derivative is contained in the ink composition of the present invention. It is preferable. That is, after printing, the ink composition is dried to form a molecular structure in which the carbonyl group site is cross-linked with a hydrazine derivative, thereby making it possible to express water resistance and abrasion resistance.
該ヒドラジン誘導体としては少なくとも２個のヒドラジン基及び／又はセミカルバジド基を有する化合物で有れば良く、これらの内、ヒドラジン基を有する化合物としてはカルボヒドラジド、イソフタル酸ジヒドラジド、マロン酸ジヒドラジド、こはく酸ジヒドラジド、グルタル酸ジヒドラジド、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド、マレイン酸ジヒドラジド、フマル酸ジヒドラジド、イタコン酸ジヒドラジド、ポリアクリル酸ヒドラジド、エチレン−１，２−ジヒドラジン、プロピレン−１，３−ジヒドラジン、ブチレン−１，４−ジヒドラジン、水加ヒドラジンなどが例示され、セミカルバジド基を有する化合物としてはポリイソシアネート化合物と該ヒドラジン化合物の反応により得られる生成物が例示される。該ヒドラジン誘導体としては、セミカルバジド基を有する化合物が、得られる画像の耐水性および耐擦性が高くより好ましい。 The hydrazine derivative may be a compound having at least two hydrazine groups and / or semicarbazide groups, and among these compounds, carbohydrazide, isophthalic acid dihydrazide, malonic acid dihydrazide, and succinic acid dihydrazide may be used. Glutaric acid dihydrazide, adipic acid dihydrazide, sebacic acid dihydrazide, maleic acid dihydrazide, fumaric acid dihydrazide, itaconic acid dihydrazide, polyacrylic acid hydrazide, ethylene-1,2-dihydrazine, propylene-1,3-dihydrazine, butylene- Examples include 1,4-dihydrazine and hydrazine hydrate, and examples of the compound having a semicarbazide group include products obtained by reacting a polyisocyanate compound and the hydrazine compound. As the hydrazine derivative, a compound having a semicarbazide group is more preferable because the obtained image has high water resistance and abrasion resistance.
セミカルバジド基を有する化合物の具体例としては、例えば下式（１）で表されるセミカルバジド誘導体、下記式（２）で表されるビスセミカルバジド類等が挙げられる。
Specific examples of the compound having a semicarbazide group include, for example, a semicarbazide derivative represented by the following formula (1), a bissemicarbazide represented by the following formula (2), and the like.
（式中、Ｒ1は、直鎖状または分岐状の炭素数２〜２０のアルキレンジイソシアネート、置換基を有しても有さなくても良い炭素数５〜２５のシクロアルキレンジイソシアネート、置換基を有しても有さなくても良い炭素数６〜２０のアリーレンジイソシアネート、及び置換基を有しても有さなくても良い炭素数８〜２０のアラルキレンジイソシアネートからなる群から選ばれる少なくとも１種のジイソシアネートの３量体〜２０量体オリゴマーに由来する、末端イソシアネート基を有さないポリイソシアネート残基、もしくはＲ1は炭素数１〜８のイソシアナトアルキル基で置換されている炭素数２〜２０のアルキレンジイソシアネートに由来する、末端イソシアネート基を有さないトリイソシアネート残基を表す。Ｒ2は、水素原子または炭素数１〜２０のアルキル基を表す。Ｒ3は、直鎖状または分岐状の炭素数１〜２０のアルキレン基、炭素数５〜２０のシクロアルキレン基、もしくは置換基を有しても有さなくても良い炭素数６〜１０のアリーレン基を表す。ｎは、０または１を表す。ｌ及びｍは、各々０または正の整数を表す。ただし、２０≧（ｌ＋ｍ）≧３である。）
(In the formula, R 1 represents a linear or branched alkylene diisocyanate having 2 to 20 carbon atoms, a cycloalkylene diisocyanate having 5 to 25 carbon atoms which may or may not have a substituent, and a substituent. At least 1 selected from the group consisting of arylene diisocyanates having 6 to 20 carbon atoms that may or may not have and those having 8 to 20 carbon atoms that may or may not have a substituent. A polyisocyanate residue having no terminal isocyanate group, derived from a trimer to a 20-mer oligomer of a kind of diisocyanate, or R 1 is substituted with an isocyanatoalkyl group having 1 to 8 carbon atoms. from 20 alkylene diisocyanate, .R 2 representing the triisocyanate residue without the terminal isocyanate groups is a hydrogen atom or Represents an alkyl group of prime 1-20 .R 3 is no have a linear or branched alkylene group having 1 to 20 carbon atoms, cycloalkylene group having 5 to 20 carbon atoms or a substituent, It may be an arylene group having 6 to 10 carbon atoms, n represents 0 or 1. l and m each represents 0 or a positive integer, provided that 20 ≧ (l + m) ≧ 3. )
（式中、Ｒ５は、直鎖状または分岐状の炭素数２〜２０の２価の脂肪族残基、炭素数６〜２５の２価の脂環族残基、置換基を有しても有さなくても良い炭素数６〜２５の２価の芳香族残基、及び置換基を有しても有さなくても良い炭素数６〜２５の２価の芳香脂環族残基を表す。Ｒ４は、水素原子または炭素数１〜２０のアルキル基を表す。） (In the formula, R 5 has a linear or branched divalent aliphatic residue having 2 to 20 carbon atoms, a divalent alicyclic residue having 6 to 25 carbon atoms, and a substituent. And a divalent aromatic residue having 6 to 25 carbon atoms that may or may not have, and a divalent aromatic alicyclic residue having 6 to 25 carbon atoms that may or may not have a substituent. R 4 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.)
上記ポリセミカルバジド化合物の中で、前記式（１）で表されるセミカルバジド誘導体は、多官能であり、架橋能力が高いことから非常に好ましい。
本発明においてヒドラジン誘導体の含有量は、インク組成物中においてヒドラジン誘導体中のヒドラジン基に対する高分子化合物（Ａ）のカルボニル基の比が、（カルボニル基）／（ヒドラジン基）モル比で０．００１〜１０の範囲であることが好ましい。
Among the polysemicarbazide compounds, the semicarbazide derivative represented by the formula (1) is very preferable because it is polyfunctional and has high crosslinking ability.
In the present invention, the content of the hydrazine derivative is such that the ratio of the carbonyl group of the polymer compound (A) to the hydrazine group in the hydrazine derivative in the ink composition is 0.001 in terms of (carbonyl group) / (hydrazine group) molar ratio. It is preferable that it is the range of -10.
本発明の着色剤は、乳化重合法、懸濁重合法、分散重合法などの高分子エマルジョンを得る方法として一般に良く知られている方法を用いて前記顔料の共存下、主モノマー（Ｂ）や副モノマー（Ｃ）を重合する方法や、溶液重合した高分子化合物（Ａ）を前記顔料と混合し、水溶媒中に界面活性剤を利用して分散させる方法などを応用することによって製造することができる。例えば水に界面活性剤を溶解し、前記主モノマー（Ｂ）、副モノマー（Ｃ）等共重合モノマー成分を加えて乳化させ、ラジカル重合開始剤を加えて前述の顔料を分散した液とともに一括仕込みによる反応により乳化重合を行う方法のほか、連続滴下、分割添加などの方法により反応系に共重合成分や、ラジカル重合開始剤を反応系に供給する方法が挙げられる。 The colorant of the present invention is prepared by using a method generally known as a method for obtaining a polymer emulsion such as an emulsion polymerization method, a suspension polymerization method, a dispersion polymerization method, etc. in the presence of the pigment in the presence of the main monomer (B) Manufactured by applying a method of polymerizing the submonomer (C), a method of mixing the polymer compound (A) polymerized with the solution with the pigment, and dispersing in a water solvent using a surfactant. Can do. For example, a surfactant is dissolved in water, and the copolymerization monomer components such as the main monomer (B) and submonomer (C) are added and emulsified, and a radical polymerization initiator is added and the above pigment is dispersed and charged together. In addition to the method of performing emulsion polymerization by the reaction according to the above, there may be mentioned a method of supplying a copolymer component or a radical polymerization initiator to the reaction system by a method such as continuous dropping or divided addition.
本発明の着色剤を製造するにおいては、界面活性剤を利用することが好ましい。例えば、脂肪酸石鹸、アルキルスルホン酸塩、アルキルスルホコハク酸塩、ポリオキシエチレンアルキル硫酸塩、ポリオキシエチレンアルキルアリール硫酸塩、ｐ−スチレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸塩、ホルマリン重縮合物、高級脂肪酸とアミノ酸の縮合物、ジアルキルスルホコハク酸エステル塩、ナフテン酸塩等、アルキルエーテルカルボン酸塩、アシル化ペプチド、α−オレフィンスルホ ン酸塩、Ｎ−アシルメチルタウリン、アルキルエーテル硫酸塩、第二級高級アルコールエトキシサルフェート、ポリオキシエチレンアルキルフェニルエーテル硫酸塩、モノグリサルフェート、アルキルエーテル燐酸エステル塩、アルキル燐酸エステル塩等のアニオン性界面活性剤や、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンソルビタン脂肪酸エステル、オキシエチレンオキシプロピレンプロックコポリマー、ポリグリセリン脂肪酸エステル等の非イオン性界面活性剤が挙げられる。 In producing the colorant of the present invention, it is preferable to use a surfactant. For example, fatty acid soap, alkyl sulfonate, alkyl sulfosuccinate, polyoxyethylene alkyl sulfate, polyoxyethylene alkyl aryl sulfate, p-styrene sulfonate, alkyl naphthalene sulfonate, naphthalene sulfonate, formalin heavy Condensates, condensates of higher fatty acids and amino acids, dialkylsulfosuccinates, naphthenates, etc., alkyl ether carboxylates, acylated peptides, α-olefin sulfonates, N-acylmethyl taurines, alkyl ether sulfates Anionic surfactants such as secondary higher alcohol ethoxy sulfate, polyoxyethylene alkyl phenyl ether sulfate, monoglyculate, alkyl ether phosphate ester, alkyl phosphate ester salt, and polyoxyethylene Alkyl aryl ethers, polyoxyethylene alkyl phenyl ethers, polyoxyethylene sorbitan fatty acid esters, oxyethylene oxypropylene Proc copolymer, nonionic surfactants such as polyglycerol fatty acid esters.
これらの界面活性剤の使用量としては、着色剤固形分１００質量部に対して０．００１〜２０質量部であることが好ましく、さらに好ましくは０．００５〜１０質量部である。
着色剤の平均粒径は、高品質の画像が得られるという観点から、微粒子径ことが好ましく、透過型電子顕微鏡を用いて測定した着色剤の数平均粒径が２０〜３００ｎｍであることが好ましく、さらには２０〜１２０ｎｍであることが好ましい。
本発明において、着色剤中の高分子化合物（Ａ）の含有量は、得られる画像の耐擦性の観点から、着色剤固形分１００質量部中、５〜８０質量部含有することが好ましく、２０〜６０質量部含有することが特に好ましい。
The amount of these surfactants to be used is preferably 0.001 to 20 parts by mass, more preferably 0.005 to 10 parts by mass with respect to 100 parts by mass of the colorant solid content.
The average particle size of the colorant is preferably a fine particle size from the viewpoint that a high-quality image can be obtained, and the number average particle size of the colorant measured using a transmission electron microscope is preferably 20 to 300 nm. Furthermore, it is preferable that it is 20-120 nm.
In the present invention, the content of the polymer compound (A) in the colorant is preferably 5 to 80 parts by mass in 100 parts by mass of the colorant solids from the viewpoint of the abrasion resistance of the obtained image. It is especially preferable to contain 20-60 mass parts.
本発明のインク組成物は、着色剤の分散液を、必要に応じて水溶解性樹脂、水および分散剤とともにサンドミル、ホモジナイザー、ボールミル、ペイントシェーカー、超音波分散機等の分散機でよく分散して濃縮状態の分散液を予め製造したのち、必要に応じて水および添加剤を加えて混合攪拌することにより、製造することができる。インク組成物は、孔径１μｍ以下、好ましくは０．８μｍ以下、さらに好ましくは０．４５μｍ以下のフィルターで濾過することが好ましい。フィルター濾過に先立って、遠心分離によって大きな粒径のものを除くこともでき、これによりフィルター濾過における目詰まりを少なくし、フィルターの使用期間を長くすることができる。 In the ink composition of the present invention, the dispersion of the colorant is well dispersed with a disperser such as a sand mill, a homogenizer, a ball mill, a paint shaker, and an ultrasonic disperser together with a water-soluble resin, water and a dispersant as necessary. Then, after the dispersion in a concentrated state is produced in advance, it can be produced by adding water and additives as needed and mixing and stirring. The ink composition is preferably filtered through a filter having a pore size of 1 μm or less, preferably 0.8 μm or less, more preferably 0.45 μm or less. Prior to filter filtration, those having a large particle size can be removed by centrifugation, thereby reducing clogging in the filter filtration and extending the service life of the filter.
本発明のインク組成物は、水および必要に応じて水性溶剤を含む水性の液体を媒体とする。水としては、金属イオン等を除去したイオン交換水ないし蒸留水を用いる。水性溶剤は、記録液のノズル部分での乾燥、記録液の固化を防止し、安定な記録液の噴射およびノズルの経時での乾燥を防止するために、単独ないし混合して記録液の０〜５０質量％の範囲で用いることが好ましい。
水性溶剤の例としてはアセトン、メチルエチルケトン、メチルブチルケトン、メチルイソブチルケトン、等のケトン類；メタノール、エタノール、２-プロパノール、２-メチル-１-プロパノール、１-ブタノール、２-メトキシエタノール、等のアルコール類；テトラヒドロフラン、１，４-ジオキサン、１，２-ジメトキシエタン、等のエーテル類；ジメチルホルムアミド、Ｎ-メチルピロリドン、等のアミド類が挙げられる。
The ink composition of the present invention uses water and an aqueous liquid containing an aqueous solvent as necessary as a medium. As water, ion-exchanged water or distilled water from which metal ions and the like are removed is used. In order to prevent the recording liquid from drying and solidifying the recording liquid, and to prevent stable recording liquid jetting and drying of the nozzle over time, the aqueous solvent may be mixed alone or mixed to form 0 to 0 of the recording liquid. It is preferable to use in the range of 50% by mass.
Examples of aqueous solvents include ketones such as acetone, methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, etc .; methanol, ethanol, 2-propanol, 2-methyl-1-propanol, 1-butanol, 2-methoxyethanol, etc. Alcohols; Ethers such as tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane; Amides such as dimethylformamide and N-methylpyrrolidone.
Ｎ置換（メタ）アクリルアミドの共重合割合が多い高分子化合物（Ａ）はある転移温度以下で親水性となり、転移温度を超える温度では疎水性となる性質を発現する。該感温性は水溶媒中で発現するが、水溶性溶剤、特にアルコール類を添加することによって高分子化合物（Ａ）の持つ転移温度を低下させ、実用温度ではインク組成物中において高分子化合物（Ａ）を疎水性に保つことが可能となる。よって、前記感温性を有する高分子化合物（Ａ）を用いる場合には、インク組成物に前記水性溶剤を添加することは好ましく、特に、アルコール類を添加することは好ましい。 The polymer compound (A) having a high copolymerization ratio of N-substituted (meth) acrylamide is hydrophilic at a certain transition temperature or lower and develops a hydrophobic property at a temperature exceeding the transition temperature. The temperature sensitivity is manifested in an aqueous solvent, but the transition temperature of the polymer compound (A) is lowered by adding a water-soluble solvent, particularly an alcohol, and the polymer compound is used in the ink composition at a practical temperature. It becomes possible to keep (A) hydrophobic. Therefore, when the polymer compound (A) having temperature sensitivity is used, it is preferable to add the aqueous solvent to the ink composition, and it is particularly preferable to add alcohols.
本発明のインク組成物には、黴の発生を防止するために、防黴剤を記録液の０．０５〜１．０質量％の範囲で添加することができる。防黴剤としては、デヒドロ酢酸ナトリウム、安息香酸ナトリウム、ソジウムピリジンチオン-１-オキサイド、ジンクピリジンチオン-１-オキサイド、１，２-ベンズイソチアゾリン-３-オン，１-ベンズイソチアゾリン-３-オンのアミン塩等が好ましく用いられる。
また、本発明のインク組成物をインクジェットプリンターで使用する場合、ノズル部での金属の析出や記録液中で不溶解性物の析出等を防止するために、キレート剤を記録液の０〜０．５質量％の範囲で用いることができる。キレート剤は記録液中の金属イオンを封鎖するものであり、具体的には、エチレンジアミンテトラアセティックアシド、エチレンジアミンテトラアセティックアシドのナトリウム塩、エチレンジアミンテトラアセティックアシドのジアンモニウム塩、エチレンジアミンテトラアセティックアシドのテトラアンモニウム塩等が挙げられる。
本発明のインク組成物に界面活性剤を必要に応じて添加しても良い。界面活性剤としては、アニオン性、カチオン性、両性イオン性、非イオン性のいずれの活性剤でも良い。
In the ink composition of the present invention, an antifungal agent can be added in the range of 0.05 to 1.0% by mass of the recording liquid in order to prevent generation of wrinkles. Antifungal agents include sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione-1-oxide, 1,2-benzisothiazolin-3-one, 1-benzisothiazoline-3-one The amine salt of is preferably used.
In addition, when the ink composition of the present invention is used in an ink jet printer, a chelating agent is added to the recording liquid in an amount of 0 to 0 in order to prevent metal precipitation at the nozzle portion and insoluble matter in the recording liquid. It can be used in the range of 0.5 mass%. The chelating agent sequesters metal ions in the recording liquid. Specifically, ethylenediaminetetraacetic acid, sodium salt of ethylenediaminetetraacetic acid, diammonium salt of ethylenediaminetetraacetic acid, ethylenediaminetetraacetic acid And tetraammonium salt of acid.
A surfactant may be added to the ink composition of the present invention as necessary. As the surfactant, any of anionic, cationic, zwitterionic and nonionic surfactants may be used.
アニオン性界面活性剤の例としては、ステアリン酸ナトリウム、オレイン酸カリウム、半硬化牛脂脂肪酸ナトリウム、等の脂肪酸塩類；ドデシル硫酸ナトリウム、ドデシル硫酸トリ（２-ヒドロキシエチル）アンモニウム、オクタデシル硫酸ナトリウム等のアルキル硫酸エステル塩類；ノニルベンゼンスルホン酸ナトリウム、ドデシルベンゼンスルホン酸ナトリウム、オクタデシルベンゼンスルホン酸ナトリウム、ドデシルジフェニルエーテルジスルホン酸ナトリウム等のベンゼンスルホン酸塩類；ドデシルナフタレンスルホン酸ナトリウム、ナフタレンスルホン酸ホルマリン縮合物等のナフタレンスルホン酸塩類；スルホコハク酸ジドデシルナトリウム、スルホコハク酸ジオクタデシルナトリウム等のスルホコハク酸エステル塩類；ポリオキシエチレンドデシルエーテル硫酸ナトリウム、ポリオキシエチレンドデシルエーテル硫酸トリ（２-ヒドロキシエチル）アンモニウム、ポリオキシエチレンオクタデシルエーテル硫酸ナトリウム、ポリオキシエチレンドデシルフェニルエーテル硫酸ナトリウム等のポリオキシエチレン硫酸エステル塩類；ドデシルリン酸カリウム、オクタデシルリン酸ナトリウム等のリン酸エステル塩類等が挙げられる。 Examples of anionic surfactants include fatty acid salts such as sodium stearate, potassium oleate, and semi-cured tallow fatty acid sodium; alkyls such as sodium dodecyl sulfate, tri (2-hydroxyethyl) ammonium dodecyl sulfate, and sodium octadecyl sulfate. Sulfate esters; benzenesulfonates such as sodium nonylbenzenesulfonate, sodium dodecylbenzenesulfonate, sodium octadecylbenzenesulfonate, sodium dodecyldiphenylether disulfonate; naphthalenesulfone such as sodium dodecylnaphthalenesulfonate, formalin condensate of naphthalenesulfonate Acid salts; sulfosuccinic acid ester salts such as sodium dododecyl sulfosuccinate and dioctadecyl sodium sulfosuccinate; polyoxy Polyoxyethylene sulfate salts such as sodium ethylene dodecyl ether sulfate, poly (2-hydroxyethyl) ammonium sulfate polyoxyethylene dodecyl ether sulfate, sodium polyoxyethylene octadecyl ether sulfate, sodium polyoxyethylene dodecyl phenyl ether sulfate; potassium dodecyl phosphate And phosphate ester salts such as sodium octadecylphosphate.
カチオン性界面活性剤の例としては、酢酸オクタデシルアンモニウム、ヤシ油アミン酢酸塩等のアルキルアミン塩類；塩化ドデシルトリメチルアンモニウム、塩化オクタデシルトリメチルアンモニウム、塩化ジオクタデシルジメチルアンモニウム、塩化ドデシルベンジルジメチルアンモニウム等の第４級アンモニウム塩類が挙げられる。
両性イオン性活性剤の例としては、ドデシルベタイン、オクタデシルベタイン等のアルキルベタイン類；ドデシルジメチルアミンオキシド等のアミンオキシド類等が挙げられる。
Examples of cationic surfactants include alkylamine salts such as octadecylammonium acetate and coconut oil amine acetate; Examples include quaternary ammonium salts.
Examples of zwitterionic activators include alkylbetaines such as dodecylbetaine and octadecylbetaine; amine oxides such as dodecyldimethylamine oxide and the like.
非イオン性界面活性剤の例としては、ポリオキシエチレンドデシルエーテル、ポリオキシエチレンヘキサデシルエーテル、ポリオキシエチレンオクタデシルエーテル、ポリオキシエチレン（９-オクタデセニル）エーテル等のポリオキシエチレンアルキルエーテル類；ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンノニルフェニルエーテル等のポリオキシエチレンフェニルエーテル類；ポリ酸化エチレン、コ-ポリ酸化エチレン酸化プロピレン等のオキシラン重合体類；ソルビタンドデカン酸エステル、ソルビタンヘキサデカン酸エステル、ソルビタンオクタデカン酸エステル、ソルビタン（９-オクタデセン酸）エステル、ソルビタン（９-オクタデセン酸）トリエステル、ポリオキシエチレンソルビタンドデカン酸エステル、ポリオキシエチレンソルビタンヘキサデカン酸エステル、ポリオキシエチレンソルビタンオクタデカン酸エステル、ポリオキシエチレンソルビタンオクタデカン酸トリエステル、ポリオキシエチレンソルビタン（９-オクタデセン酸）エステル、ポリオキシエチレンソルビタン（９-オクタデセン酸）トリエステル等のソルビタン脂肪酸エステル類；ポリオキシエチレンソルビトール（９-オクタデセン酸）テトラエステル等のソルビトール脂肪酸エステル類；グリセリンオクタデカン酸エステル、グリセリン（９-オクタデセン酸）エステル等のグリセリン脂肪酸エステル類が挙げられる。これらの非イオン性活性剤の中でもＨＬＢが１４以上のものが特に好ましい。 Examples of nonionic surfactants include polyoxyethylene dodecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene octadecyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene (9-octadecenyl) ether; polyoxy Polyoxyethylene phenyl ethers such as ethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether; oxirane polymers such as polyethylene oxide and co-polyethylene oxide propylene oxide; sorbitan dodecanoate, sorbitan hexadecanoate, sorbitan octadecane Acid ester, sorbitan (9-octadecenoic acid) ester, sorbitan (9-octadecenoic acid) triester, polyoxyethylene sorbitan dodecanoate ester , Polyoxyethylene sorbitan hexadecanoic acid ester, polyoxyethylene sorbitan octadecanoic acid ester, polyoxyethylene sorbitan octadecanoic acid triester, polyoxyethylene sorbitan (9-octadecenoic acid) ester, polyoxyethylene sorbitan (9-octadecenoic acid) tri Examples include sorbitan fatty acid esters such as esters; sorbitol fatty acid esters such as polyoxyethylene sorbitol (9-octadecenoic acid) tetraester; and glycerin fatty acid esters such as glycerin octadecanoic acid ester and glycerin (9-octadecenoic acid) ester. Among these nonionic active agents, those having an HLB of 14 or more are particularly preferred.
本発明のインク組成物に水溶性樹脂を添加してもよい。該水溶性樹脂の例としては、にかわ、ゼラチン、カゼイン、アルブミン、アラビアゴム、フィッシュグリュー、アルギン酸、メチルセルロース、カルボキシメチルセルロース、ヒドロキシエチルセルロース、ポリ酸化エチレン、ポリビニルアルコール、ポリアクリルアミド、ポリアクリル酸、ポリビニルエーテル、ポリビニルピロリドン、スチレン-マレイン酸共重合体、スチレン-アクリル酸共重合体、アクリル酸エステル-アクリル酸共重合体等が挙げられる。
水溶性樹脂は、インク組成物の粘度調節などの目的で必要に応じて使用されるものであり、インク組成物に使用する場合のインク組成物中の水溶性樹脂の含有割合は、質量基準で、３０％以下が好ましく、２０％以下が特に好ましい。
A water-soluble resin may be added to the ink composition of the present invention. Examples of the water-soluble resin include glue, gelatin, casein, albumin, gum arabic, fish mulled, alginic acid, methyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, polyethylene oxide, polyvinyl alcohol, polyacrylamide, polyacrylic acid, polyvinyl ether, Examples thereof include polyvinylpyrrolidone, styrene-maleic acid copolymer, styrene-acrylic acid copolymer, and acrylate-acrylic acid copolymer.
The water-soluble resin is used as necessary for the purpose of adjusting the viscosity of the ink composition, and the content of the water-soluble resin in the ink composition when used in the ink composition is based on mass. 30% or less is preferable, and 20% or less is particularly preferable.
以下、本発明を実施例に基づいて説明する。
以下の実施例及び比較例において、「部」および「％」は、「質量部」および「質量％」を表わす。
実施例および比較例において、画像耐擦性、光沢むら、発色性および耐水性の各評価を以下に示す基準で行った。
（画像耐擦性の評価）
印刷後３０分経過した記録物の画像部を、指で強く擦り、以下の判断基準に従って評価した。
○：汚れは全く生じない
△：わずかに汚れる
×： 汚れる
Hereinafter, the present invention will be described based on examples.
In the following examples and comparative examples, “parts” and “%” represent “parts by mass” and “mass%”.
In Examples and Comparative Examples, evaluation of image rubbing resistance, uneven gloss, color developability and water resistance was performed according to the following criteria.
(Evaluation of image abrasion resistance)
The image portion of the recorded matter 30 minutes after printing was rubbed strongly with a finger and evaluated according to the following criteria.
○: No dirt is produced Δ: Slightly dirty ×: Dirty
（光沢ムラの評価）
印刷後３０分経過した記録物の、白紙部（未印刷部）の光沢感と画像部の光沢感の違いを目視によって官能的に評価し、以下の判定を行った。
○：光沢感の違いがほとんど気にならない。
△：光沢感の違いが認められるが、目立たない。
×：光沢の違いが気になる。
(Evaluation of uneven gloss)
The difference between the glossiness of the blank paper portion (unprinted portion) and the glossiness of the image portion of the recorded matter 30 minutes after printing was sensoryly evaluated visually, and the following determinations were made.
○: Little difference in glossiness.
Δ: Difference in glossiness is recognized, but not noticeable.
X: The difference in gloss is worrisome.
（発色性の評価）
印刷後３０分経過した記録物の画像部の発色を目視によって官能的に評価し、以下の判定を行った。
○：鮮明な発色であり、色濃度も高い。
△：わずかに霞が掛かったような感じはあるが、色濃度は高い。
×：霞が掛かったような感じがあり、色濃度は低い。
(Evaluation of color development)
The color development of the image portion of the recorded matter 30 minutes after printing was sensoryly evaluated by visual observation, and the following determinations were made.
○: Clear color development and high color density.
Δ: The color density is high although there is a feeling of slight wrinkles.
X: Feels like wrinkles and color density is low.
（耐水性の評価）
印刷後１日経過した記録物を、１０分間水に浸漬した時の色のにじみ、流れだしの有無を目視にて評価した。
○：インキのにじみ、流れだしなし。
△：わずかにインキのにじみはあるが、流れだしはない。
×：インキのにじみ、流れだしあり。
(Evaluation of water resistance)
One day after printing, the recorded matter was visually evaluated for the presence of bleeding and color bleeding when immersed in water for 10 minutes.
○: No ink bleed or flow.
Δ: Slight ink bleeding but no flow.
X: Ink bleed and run out.
（調製例１）
攪拌機、還流管、温度計を有する反応容器にメチルエチルケトン２５０部、Ｎ−イソプロピルアクリルアミド９０部、メチルメタクリレート３０部、スチレン１０部、２−ヒドロキシエチルメタクリレート５部、メタクリル酸５部、ダイアセトンアクリルアミド１０部を仕込み、窒素置換した後攪拌しながら７０℃に加熱した。重合開始剤としてｔ−ブチルパーオキシオクトエート１．５部を５０部のメチルエチルケトンに溶解した溶液を滴下ロートから反応容器に４時間かけ徐々に添加して反応させ、更に２時間７０℃で攪拌を続けた後、室温まで冷却し、高分子化合物溶液１を得た。
(Preparation Example 1)
In a reaction vessel having a stirrer, a reflux tube and a thermometer, 250 parts of methyl ethyl ketone, 90 parts of N-isopropylacrylamide, 30 parts of methyl methacrylate, 10 parts of styrene, 5 parts of 2-hydroxyethyl methacrylate, 5 parts of methacrylic acid, 10 parts of diacetone acrylamide Was replaced with nitrogen and heated to 70 ° C. with stirring. As a polymerization initiator, a solution of 1.5 parts of t-butyl peroxyoctoate dissolved in 50 parts of methyl ethyl ketone was gradually added from the dropping funnel to the reaction vessel over 4 hours to react, and further stirred at 70 ° C. for 2 hours. After continuing, it cooled to room temperature and obtained the high molecular compound solution 1.
（調製例２）
攪拌機、還流管、温度計を有する反応容器にメチルエチルケトン２５０部、ｎ−ブチルメタクリレート９５部、メチルメタクリレート２０部、スチレン１０部、２−ヒドロキシエチルメタクリレート１０部、メタクリル酸５部、メタクリルアミド１０部を仕込み、窒素置換した後攪拌しながら７０℃に加熱した。重合開始剤としてｔ−ブチルパーオキシオクトエート１．５部を５０部のメチルエチルケトンに溶解した溶液を滴下ロートから反応容器に４時間かけ徐々に添加して反応させ、更に２時間７０℃で攪拌を続けた後、室温まで冷却し、高分子化合物溶液２を得た。
(Preparation Example 2)
In a reaction vessel having a stirrer, a reflux tube and a thermometer, 250 parts of methyl ethyl ketone, 95 parts of n-butyl methacrylate, 20 parts of methyl methacrylate, 10 parts of styrene, 10 parts of 2-hydroxyethyl methacrylate, 5 parts of methacrylic acid, and 10 parts of methacrylamide. After charging and replacing with nitrogen, the mixture was heated to 70 ° C. with stirring. As a polymerization initiator, a solution of 1.5 parts of t-butyl peroxyoctoate dissolved in 50 parts of methyl ethyl ketone was gradually added from the dropping funnel to the reaction vessel over 4 hours to react, and further stirred at 70 ° C. for 2 hours. After continuing, it cooled to room temperature and obtained the high molecular compound solution 2.
（調製例３）
攪拌機を有する反応容器に調製例１で得られた高分子化合物溶液１を１２０部、カーボンブラック（三菱＃９６０、三菱化学（株）製）８０部、水２００部を仕込み、攪拌、混合した。混合液を直径０．３ｍｍのジルコニアビーズを充填した分散装置（ＳＣミルＳＣ１００／３２型、三井鉱山（株）製）に通し、循環方式により５時間分散した。分散装置の回転数は２７００回転／分とし、冷却用ジャケットには冷水を通して分散液温度が４０℃以下に保たれるようにした。
分散終了後、混合槽より分散原液を抜き採り、次いで水１０００部で混合槽および分散装置流路を洗浄し、分散原液と合わせて希釈分散液を得た。希釈分散液をガラス製蒸留装置に入れ、メチルエチルケトンの全量と水の一部を減圧下で留去し、０．１ｍｏｌ／Ｌの水酸化ナトリウムで中和してｐＨ９に調整してから０．３μｍのメンブレンフィルターでろ過して、不揮発分が２０％の着色剤分散液１を得た。
粒度分析計（マイクロトラックＵＰＡ１５０型、リーズ＆ノースロップ社製）で測定した着色剤１の数平均粒径は９０ｎｍであった。
(Preparation Example 3)
In a reaction vessel having a stirrer, 120 parts of the polymer compound solution 1 obtained in Preparation Example 1, 80 parts of carbon black (Mitsubishi # 960, manufactured by Mitsubishi Chemical Corporation), and 200 parts of water were charged, stirred, and mixed. The mixed solution was passed through a dispersing device (SC mill SC100 / 32 type, manufactured by Mitsui Mining Co., Ltd.) filled with zirconia beads having a diameter of 0.3 mm, and dispersed for 5 hours by a circulation method. The number of revolutions of the dispersing device was 2700 rpm, and the temperature of the dispersion was kept at 40 ° C. or less through the cooling jacket through cold water.
After the dispersion, the dispersion stock solution was extracted from the mixing tank, and then the mixing tank and the dispersion apparatus flow path were washed with 1000 parts of water, and a diluted dispersion liquid was obtained together with the dispersion stock solution. The diluted dispersion is put into a glass distillation apparatus, and all of methyl ethyl ketone and a part of water are distilled off under reduced pressure, neutralized with 0.1 mol / L sodium hydroxide and adjusted to pH 9 and then 0.3 μm A colorant dispersion 1 having a nonvolatile content of 20% was obtained by filtration through a membrane filter.
The number average particle diameter of the colorant 1 measured with a particle size analyzer (Microtrac UPA150 type, manufactured by Leeds & Northrop Co.) was 90 nm.
（調製例４）
調製例３で用いた高分子化合物溶液１のかわりに高分子化合物溶液２を用いる以外全く同様にして不揮発分が２０％の着色剤分散液２を得た。
粒度分析計（マイクロトラックＵＰＡ１５０型、リーズ＆ノースロップ社製）で測定した着色剤２の数平均粒径は９０ｎｍであった。
(Preparation Example 4)
A colorant dispersion 2 having a non-volatile content of 20% was obtained in exactly the same manner except that the polymer compound solution 2 was used instead of the polymer compound solution 1 used in Preparation Example 3.
The number average particle diameter of the colorant 2 measured by a particle size analyzer (Microtrac UPA150 type, manufactured by Leeds & Northrop Co.) was 90 nm.
（調製例５）
カーボンブラック（三菱＃９６０、三菱化学（株）製）８０部、ポリエチレングリコール（ポリエチレングリコール３００、東京化成製）２０部、非イオン性活性剤（エマルゲンＡ-９０、花王製）１部、水３００部を、直径０．３ｍｍのジルコニアビーズを充填した分散装置（ＳＣミルＳＣ１００／３２型、三井鉱山（株）製）に通し、循環方式により５時間分散した。分散装置の回転数は２７００回転／分とし、冷却用ジャケットには冷水を通して分散液温度が４０℃以下に保たれるようにした。濾過、水洗を２回繰り返し、不揮発分が２０％の着色剤分散液３を得た。
粒度分析計（マイクロトラックＵＰＡ１５０型、リーズ＆ノースロップ社製）で測定した着色剤３の数平均粒径は７０ｎｍであった。
(Preparation Example 5)
80 parts of carbon black (Mitsubishi # 960, manufactured by Mitsubishi Chemical Corporation), 20 parts of polyethylene glycol (polyethylene glycol 300, manufactured by Tokyo Chemical Industry), 1 part of nonionic active agent (Emulgen A-90, manufactured by Kao), water 300 The part was passed through a dispersing device (SC mill SC100 / 32 type, manufactured by Mitsui Mining Co., Ltd.) filled with zirconia beads having a diameter of 0.3 mm, and dispersed for 5 hours by a circulation method. The number of revolutions of the dispersing device was 2700 rpm, and the temperature of the dispersion was kept at 40 ° C. or less through the cooling jacket through cold water. Filtration and washing with water were repeated twice to obtain a colorant dispersion 3 having a nonvolatile content of 20%.
The number average particle diameter of the colorant 3 measured by a particle size analyzer (Microtrac UPA150 type, manufactured by Leeds & Northrop Co.) was 70 nm.
（調製例６）
下記の原料を混合したのち０．４５μｍの メンブランフィルターで濾過し，インク組成物１を得た。
調製例３で得られた着色剤分散液１ ５０部
非イオン性活性剤（エマルゲンＡ-９０、花王製） ０．１部
トリエタノールアミン ２部
エチレングリコール ２８部
グリセリン ２０部
精製水 ３５０部
(Preparation Example 6)
The following raw materials were mixed and then filtered through a 0.45 μm membrane filter to obtain ink composition 1.
Colorant dispersion 1 obtained in Preparation Example 3 50 parts Nonionic activator (Emulgen A-90, manufactured by Kao) 0.1 part Triethanolamine 2 parts Ethylene glycol 28 parts Glycerin 20 parts Purified water 350 parts
（調製例７）
下記の原料を混合したのち０．４５μｍの メンブランフィルターで濾過し，インク組成物２を得た。
調製例３で得られた着色剤分散液１ ５０部
調製例１０で得られたポリセミカルバジド化合物 ０．５部
非イオン性活性剤（エマルゲンＡ-９０、花王製） ０．１部
トリエタノールアミン ２部
エチレングリコール ２８部
グリセリン ２０部
精製水 ３５０部
(Preparation Example 7)
The following raw materials were mixed and then filtered through a 0.45 μm membrane filter to obtain ink composition 2.
Colorant dispersion 1 obtained in Preparation Example 3 50 parts Polysemicarbazide compound obtained in Preparation Example 0.5 0.5 part Nonionic active agent (Emulgen A-90, manufactured by Kao) 0.1 part Triethanolamine 2 Part ethylene glycol 28 parts glycerin 20 parts purified water 350 parts
（調製例８）
調製例６で用いた着色剤分散液１のかわりに着色剤分散液２を用いる以外全く同様にしてインク組成物３を得た。
（調製例９）
調製例６で用いた着色剤分散液１のかわりに着色剤分散液３を用いる以外全く同様にしてインク組成物４を得た。
(Preparation Example 8)
Ink composition 3 was obtained in exactly the same manner except that colorant dispersion 2 was used instead of colorant dispersion 1 used in Preparation Example 6.
(Preparation Example 9)
Ink composition 4 was obtained in exactly the same manner except that colorant dispersion 3 was used instead of colorant dispersion 1 used in Preparation Example 6.
（調製例１０）
ヘキサメチレンジイソシアネート１６８部、ビュレット化剤としての水１．５部を、エチレングリコールメチルエーテルアセテートとリン酸トリメチルの１：１（質量比）の混合溶媒１３０部に溶解し、反応温度１６０℃にて１時間反応させた。得られた反応液を薄膜蒸留缶を用いて、１回目は１３３Ｐａ／１６０℃の条件下、２回目は１３．３Ｐａ／２００℃の条件下にて２段階の処理により余剰のヘキサメチレンジイソシアネート、及び溶媒を留去回収し、残留物を得た。得られた残留物は、９９．９質量％のポリイソシアネート（ヘキサメチレンジイソシアネートのビュウレット型ポリイソシアネート）及び０．１質量％の残存ヘキサメチレンジイソシアネートを含んでいた。得られた残留物の粘度は１９００（±２００）ｍＰａ．ｓ／２５℃、数平均分子量は約６００（±１００）であり、平均−ＮＣＯ官能基数は約３．３、−ＮＣＯ基含有量は２３．３質量％であった。
(Preparation Example 10)
168 parts of hexamethylene diisocyanate and 1.5 parts of water as a burette agent are dissolved in 130 parts of a 1: 1 (mass ratio) mixed solvent of ethylene glycol methyl ether acetate and trimethyl phosphate, and the reaction temperature is 160 ° C. The reaction was carried out for 1 hour. Using the thin film distillation can, the obtained reaction liquid was subjected to a second process under the condition of 133 Pa / 160 ° C. for the first time and 13.3 Pa / 200 ° C. for the second time, and excess hexamethylene diisocyanate. The solvent was removed by distillation to obtain a residue. The resulting residue contained 99.9% by weight of polyisocyanate (a hexamethylene diisocyanate burette type polyisocyanate) and 0.1% by weight of residual hexamethylene diisocyanate. The viscosity of the obtained residue was 1900 (± 200) mPa.s. The number average molecular weight was s / 25 ° C., the number average molecular weight was about 600 (± 100), the average number of —NCO functional groups was about 3.3, and the —NCO group content was 23.3 mass%.
還流冷却器、温度計及び撹拌装置を有する反応器にイソプロピルアルコール１０００部にヒドラジン１水和物８０部を撹拌しながら約３０分かけて室温で添加した後、上記ポリイソシアネート（ＮＣＯ基含量２３．３質量％）１４４部をテトラヒドロフラン５７６部に溶解した溶液を１０℃にて約１時間かけて添加し、さらに４０℃にて３時間撹拌を続け、１０００部の水を添加した。続いて得られた反応液中のイソプロピルアルコール、ヒドラジン、テトラヒドロフラン、水等を加熱減圧下に留去することにより１６８部のビウレット構造を有するポリセミカルバジド化合物を得た。平均セミカルバジド残基数を測定したところ、４．６ｍｅｑ／ｇであった。 To a reactor having a reflux condenser, a thermometer and a stirrer, 80 parts of hydrazine monohydrate was added to 1000 parts of isopropyl alcohol with stirring at room temperature over about 30 minutes, and then the polyisocyanate (NCO group content 23. (3% by mass) A solution of 144 parts dissolved in 576 parts of tetrahydrofuran was added at 10 ° C. over about 1 hour, and further stirred at 40 ° C. for 3 hours, and 1000 parts of water was added. Subsequently, isopropyl alcohol, hydrazine, tetrahydrofuran, water and the like in the obtained reaction solution were distilled off under heating and reduced pressure to obtain 168 parts of a polysemicarbazide compound having a biuret structure. When the average number of semicarbazide residues was measured, it was 4.6 meq / g.
（調製例１１）
乾式シリカ（Ａ３００、日本アエロジル（株）製）に固形分１８質量％となるように水を加え、超音波分散機を使用して分散させた後、カチオン性ポリマー（アデカカチオエースＤＭ−２０Ａ、旭電化工業（株）製）２０質量％水溶液を、乾式シリカ／カチオン性ポリマー＝１００／５（乾燥質量比）となるよう添加した後、再度超音波分散機を使用して分散させた。該分散液を５０℃に加熱し、これにポリビニルアルコール（クラレポバールＰＶＡ２３５、（株）クラレ製）を、乾式シリカ／ポリビニルアルコール＝１００／１７（乾燥質量比）となる割合で添加、混合した後、該混合液に、ホウ酸／ホウ砂／水＝１／１／１８の質量比で溶解させた水溶液を、ポリビニルアルコール／（ホウ酸＋ホウ砂）＝２０／１（乾燥質量比）となる割合で５０℃にて添加、混合し塗工液を作成した。表面に親水化処理を施したポリエチレンテレフタレート製シート（厚さ１００μｍ）に、５０℃に加温したバーコーターで前記５０℃の塗工液を塗布した後、速やかに１０℃の冷風を塗工膜表面に送風を開始した。このとき塗工膜は冷風を送風開始後速やかに増粘する現象が観察された。冷風を３０秒送風した後、続けて６０℃の温風を塗工膜表面に送風乾燥し、厚さ約４０μｍのインク吸収層を設けた記録媒体１を得た。
(Preparation Example 11)
Water was added to dry silica (A300, manufactured by Nippon Aerosil Co., Ltd.) to a solid content of 18% by mass and dispersed using an ultrasonic disperser, and then a cationic polymer (Adekathioace DM-20A, Asahi Denka Kogyo Co., Ltd.) 20% by mass aqueous solution was added so that dry silica / cationic polymer = 100/5 (dry mass ratio), and then dispersed again using an ultrasonic disperser. The dispersion is heated to 50 ° C., and polyvinyl alcohol (Kuraray Poval PVA235, manufactured by Kuraray Co., Ltd.) is added and mixed in a ratio of dry silica / polyvinyl alcohol = 100/17 (dry mass ratio). An aqueous solution prepared by dissolving boric acid / borax / water = 1/1/18 in the mixed solution becomes polyvinyl alcohol / (boric acid + borax) = 20/1 (dry mass ratio). A coating liquid was prepared by adding and mixing at a rate of 50 ° C. After applying the coating liquid at 50 ° C. with a bar coater heated to 50 ° C. on a polyethylene terephthalate sheet (thickness: 100 μm) whose surface has been subjected to hydrophilic treatment, the coating film is quickly applied with cold air at 10 ° C. Blowing started on the surface. At this time, a phenomenon was observed in which the coating film thickened quickly after the start of blowing cold air. After blowing cold air for 30 seconds, 60 ° C. hot air was continuously blown and dried on the surface of the coating film to obtain a recording medium 1 provided with an ink absorbing layer having a thickness of about 40 μm.
［実施例１］
調製例６で得られたインク組成物１をインクジェットプリンター（ＰＭ７７０Ｃ、セイコーエプソン社製）のブラックインクカートリッジに充填し、調製例１１で得られた記録媒体１に、縦４ｃｍ、横１０ｃｍの横方向のグラデーションパターンを印刷した。印刷モードは「インク：黒、用紙設定：普通紙、モード設定：推奨設定」を選択した。
得られた記録物について前述の各評価を行い、結果を表１に記した。
[Example 1]
The ink composition 1 obtained in Preparation Example 6 was filled in a black ink cartridge of an ink jet printer (PM770C, manufactured by Seiko Epson Corporation), and the recording medium 1 obtained in Preparation Example 11 was 4 cm long and 10 cm wide. The gradation pattern was printed. As the print mode, “ink: black, paper setting: plain paper, mode setting: recommended setting” was selected.
Each of the above evaluations was performed on the obtained recorded matter, and the results are shown in Table 1.
［実施例２］
調製例６で得られたインク組成物１の代わりに調製例７で得られたインク組成物２を用いる以外は全て実施例１と同様に行い、結果を表１に記した。
[Example 2]
The same procedure as in Example 1 was performed except that the ink composition 2 obtained in Preparation Example 7 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
［実施例３］
調製例１１で得られた記録媒体１の代わりに市販の普通紙（ＥＰ・Ｒ紙；富士ゼロックスオフィスサプライ株式会社製）を用いる以外は全て実施例１と同様に行い、結果を表１に記した。
[Example 3]
The same procedure as in Example 1 was performed except that commercially available plain paper (EP • R paper; manufactured by Fuji Xerox Office Supply Co., Ltd.) was used instead of the recording medium 1 obtained in Preparation Example 11, and the results are shown in Table 1. did.
［実施例４］
調製例６で得られたインク組成物１の代わりに調製例７で得られたインク組成物２を用いる以外は全て実施例３と同様に行い、結果を表１に記した。
[Example 4]
The same procedure as in Example 3 was performed except that the ink composition 2 obtained in Preparation Example 7 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
［比較例１］
調製例６で得られたインク組成物１の代わりに調製例８で得られたインク組成物３を用いる以外は全て実施例１と同様に行い、結果を表１に記した。
[Comparative Example 1]
The same procedure as in Example 1 was performed except that the ink composition 3 obtained in Preparation Example 8 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
［比較例２］
調製例６で得られたインク組成物１の代わりに調製例９で得られたインク組成物４を用いる以外は全て実施例１と同様に行い、結果を表１に記した。
[Comparative Example 2]
The same procedure as in Example 1 was performed except that the ink composition 4 obtained in Preparation Example 9 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
［比較例３］
調製例６で得られたインク組成物１の代わりに調製例８で得られたインク組成物３を用いる以外は全て実施例３と同様に行い、結果を表１に記した。
[Comparative Example 3]
The same procedure as in Example 3 was performed except that the ink composition 3 obtained in Preparation Example 8 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
［比較例４］
調製例６で得られたインク組成物１の代わりに調製例９で得られたインク組成物４を用いる以外は全て実施例３と同様に行い、結果を表１に記した。
[Comparative Example 4]
The same procedure as in Example 3 was performed except that the ink composition 4 obtained in Preparation Example 9 was used instead of the ink composition 1 obtained in Preparation Example 6, and the results are shown in Table 1.
本発明のインク組成物および記録方法を用いれば、従来技術では困難であった、高い画像品質と同時に耐光性、耐水性、耐擦性などの画像の保存安定性に優れた記録物を得ることが可能になり、インク組成物および記録方法分野の産業上の利用価値は甚だ大きなものである。 By using the ink composition and the recording method of the present invention, it is possible to obtain a recorded matter having high image quality and excellent image storage stability such as light resistance, water resistance and abrasion resistance, which has been difficult with the prior art. Therefore, the industrial utility value of the ink composition and recording method fields is extremely large.
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