JP2004083892A - Water-soluble monoazo compound and aqueous magenta ink composition and colored article - Google Patents
Water-soluble monoazo compound and aqueous magenta ink composition and colored article Download PDFInfo
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- JP2004083892A JP2004083892A JP2003187689A JP2003187689A JP2004083892A JP 2004083892 A JP2004083892 A JP 2004083892A JP 2003187689 A JP2003187689 A JP 2003187689A JP 2003187689 A JP2003187689 A JP 2003187689A JP 2004083892 A JP2004083892 A JP 2004083892A
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- -1 monoazo compound Chemical class 0.000 title claims abstract description 147
- 239000000203 mixture Substances 0.000 title claims description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 238000004040 coloring Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 239000012736 aqueous medium Substances 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical group 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 59
- 239000000976 ink Substances 0.000 description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000123 paper Substances 0.000 description 27
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 15
- 238000001454 recorded image Methods 0.000 description 15
- 238000009833 condensation Methods 0.000 description 14
- 230000005494 condensation Effects 0.000 description 14
- 238000007796 conventional method Methods 0.000 description 14
- 239000000975 dye Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 239000003125 aqueous solvent Substances 0.000 description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- RKKZDGOUSIOSIY-UHFFFAOYSA-N 4-benzamido-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C=12C(O)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=1NC(=O)C1=CC=CC=C1 RKKZDGOUSIOSIY-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000000740 bleeding effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 0 *c1cc(Nc2nc(Nc(cc3N=Nc(c(O)c(c(*c4ccccc4)cc(S(O)(=O)=O)c4)c4c4)c4S(O)(=O)=O)ccc3S(O)(=O)=O)nc(-c(cc3)cc(C(O)=O)c3O)n2)cc(C(O)=O)c1 Chemical compound *c1cc(Nc2nc(Nc(cc3N=Nc(c(O)c(c(*c4ccccc4)cc(S(O)(=O)=O)c4)c4c4)c4S(O)(=O)=O)ccc3S(O)(=O)=O)nc(-c(cc3)cc(C(O)=O)c3O)n2)cc(C(O)=O)c1 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-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
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical group OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
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- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000003429 antifungal agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
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- 238000004043 dyeing Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
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- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000000758 substrate Substances 0.000 description 2
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LZSHYKPUQCQJOP-UHFFFAOYSA-N 1,4-diethoxy-1,4-dioxobutane-2-sulfonic acid Chemical compound CCOC(=O)CC(S(O)(=O)=O)C(=O)OCC LZSHYKPUQCQJOP-UHFFFAOYSA-N 0.000 description 1
- MHEOPPXVBHKOHC-UHFFFAOYSA-N 2,2-diethyl-3-hexyl-3-sulfobutanedioic acid;2,2-dioctyl-3-sulfobutanedioic acid Chemical compound CCCCCCC(C(O)=O)(S(O)(=O)=O)C(CC)(CC)C(O)=O.CCCCCCCCC(C(O)=O)(C(C(O)=O)S(O)(=O)=O)CCCCCCCC MHEOPPXVBHKOHC-UHFFFAOYSA-N 0.000 description 1
- LXOFYPKXCSULTL-UHFFFAOYSA-N 2,4,7,9-tetramethyldec-5-yne-4,7-diol Chemical compound CC(C)CC(C)(O)C#CC(C)(O)CC(C)C LXOFYPKXCSULTL-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- NUYADIDKTLPDGG-UHFFFAOYSA-N 3,6-dimethyloct-4-yne-3,6-diol Chemical compound CCC(C)(O)C#CC(C)(O)CC NUYADIDKTLPDGG-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、水溶性モノアゾ化合物、水性マゼンタインク組成物および着色体に関する。
【０００２】
【従来の技術】
各種カラー記録法の中で、その代表的方法の一つであるインクジェットプリンタによる記録方法において、インクの各種吐出方式が開発されているが、いずれもインクの小滴を発生させ、これを種々の被記録材料（紙、フィルム、布帛等）に付着させ記録を行うものである。これは、記録ヘッドと被記録材料とが接触しない為、音の発生がなく静かであり、また小型化、高速化、カラー化が容易という特長の為、近年急速に普及しつつあり、今後とも大きな伸長が期待されている。この中で、コンピューターのカラーディスプレー上の画像又は文字情報をインクジェットプリンタによりカラ−で記録するには、一般にはイエロー、マゼンタ、シアン、ブラックの４色のインクによる減法混色で表現される。ＣＲＴディスプレー等のＲ、Ｇ、Ｂによる加法混色画像を減法混色画像で出きるだけ忠実に再現するには、使用するインクの色相及び鮮明性が重要である。又、インク組成物は長期の保存に対し安定であり、プリントした画像の濃度が高く、しかも耐水性、耐光性、耐オゾン性等の堅牢度に優れている事が求められている。
耐オゾンガス性とは、空気中に存在する酸化作用を持つオゾンガスが記録紙中で染料と反応し、印刷された画像を変退色させるという現象に対する耐性のことである。このオゾンガスは、インクジェット記録画像の退色現象を促進させているとされている最も大きな要因とされている。この変退色現象はインクジェット画像に特徴的なものであるため、耐オゾンガス性の向上は重要な課題となっている。特に、写真画質インクジェット専用紙の表面に設けられるインク受容層には、インクの乾燥を早め、また高画質でのにじみを少なくする為に、多孔質の無機物素材を用いているものが多く、このような記録紙上でオゾンガスによる変退色が顕著に見られている。
今後、インクを用いた印刷方法の使用分野を拡大すべく、広告等の展示物に活用した場合、光（電灯、蛍光灯、日光等）に暴される場合が多くなるため、インクジェット記録用に用いられるインク組成物及びそれによって着色された着色体には、耐水性、耐光性、耐湿性の他に、特に耐オゾンガス性の向上が強く求められてきている。
これらを解決するため、例えば特許文献１〜特許文献９等多くの出願がされているが、市場の要求を完全に満足するには至っていない。
【特許文献１】
特開平４−２７９６７１号公報
【特許文献２】
特開平６−３２９９３３号公報
【特許文献３】
特開平８−７３７９１号公報
【特許文献４】
特開平８−１１３７４５号公報
【特許文献５】
特開平１０−４６０４５号公報
【特許文献６】
特開平１０−３２９４０３号公報
【特許文献７】
特開平１１−１５８４２９号公報
【特許文献８】
特開２０００−２６５０９９号公報
【特許文献９】
特開２００１−７２８８６号公報
【特許文献１０】
特公昭３５−１２７８４号公報
【０００３】
【発明が解決しようとする課題】
本発明は水に溶解性が高く、長期間保存した場合でも安定であり、かつ印字された画像の濃度が高く、しかも耐オゾン性、耐光性、耐水性に優れた、人に対してより安全性の高いマゼンタ色の水溶性モノアゾ化合物およびそれを含有するインク組成物を提供する事を目的とする。
【０００４】
【課題を解決するための手段】
本発明者らは前記したような課題を解決すべく鋭意研究を重ねた結果、本発明に至ったものである。即ち本発明は、
（１）下記式（１）
【化８】
（２）下記式（１）
【化９】
（３）塩がリチウム塩、ナトリウム塩、カリウム塩または式（２）
【化１０】
（４）式（１）において、Ｘ、Ｙがそれぞれ独立にアミノ基；置換もしくは非置換のアニリノ基；置換もしくは非置換のピリジニウム基；置換もしくは非置換のベンジルアミノ基；置換基としてカルボキシル基、スルホン酸基、水酸基シアノ基、炭素数１〜４のアルコキシ基、ヒドロキシ１〜４のアルコキシ基を１〜２個有してもよいアルキルアミノ基；炭素数１〜４のアルコキシ基を１〜２個有してもよいジアルキルアミノ基、モルホリノ基、アリルアミノ基、ジアリルアミノ基；置換もしくは非置換の第４級アンモニウム基；シクロヘキシルアミノ基；水酸基；炭素数１〜４のアルコキシ基；置換もしくは非置換のフェノキシ基、ベンジルオキシ基、シクロヘキシルオキシ基；ヒドロキシ基、シアノ基、アルコキシ基、ヒドロキシアルコキシ基、スルホン酸基、またはカルボキシル基で置換されていてもよいアルキルメルカプト基、Ａがスルホン酸基、Ｂが−ＣＯ、Ｒがフェニル基、フェニルアセチル基、フェノキシアセチル基、ｍが１である（１）から（３）のいずれか一項に記載のモノアゾ化合物またはその塩、
（５）式（１）において、Ｘ、Ｙがそれぞれ独立にアミノ基；置換基として炭素数１〜８のアルキル基、スルホン酸基、カルボキシル基、ヒドロキシル基、モロホリノ基を１〜２個有してもよいアニリノ基、ピリジニウム基；ベンジルアミノ基；置換基としてカルボキシル基、スルホン酸基、水酸基シアノ基、炭素数１〜４のアルコキシ基、ヒドロキシ１〜４のアルコキシ基を１〜２個有してもよい炭素数１〜６アルキルアミノ基；炭素数１〜４のアルコキシ基アルキルアミノ基；炭素数１〜４のアルコキシ基を１〜２個有してもよいジアルキルアミノ基、モルホリノ基、アリルアミノ基、ジアリルアミノ基；置換基として炭素数１〜４のアルキル基、１，４−ジアザビシクロ−（２，２，２）−オクタン基を有してもよい第４級アンモニウム基；シクロヘキシルアミノ基；水酸基；炭素数１〜４のアルコキシ基；置換基として炭素数１〜８のアルキル基、スルホン酸基、カルボキシル基を有してもよいフェノキシ基、ベンジルオキシ基、シクロヘキシルオキシ基；ヒドロキシ基、シアノ基、アルコキシ基、ヒドロキシアルコキシ基、スルホン酸基、またはカルボキシル基で置換されていてもよい炭素数１〜６アルキルメルカプト基、Ａがスルホン酸基、Ｂが−ＣＯ、Ｒがフェニル基、ｍが１である（１）から（４）のいずれか一項に記載のモノアゾ化合物またはその塩、
（６）骨格として下記式（３）
【化１１】
（７）骨格として下記式（４）
【化１２】
（８）（１）から（５）のいずれか１項に記載のモノアゾ化合物またはその塩を含むことを特徴とする水性マゼンタインク組成物、
（９）骨格として下記式（３）
【化１３】
（１０）骨格として下記式（４）
【化１４】
（１１）インク滴を記録信号に応じて吐出させて被記録材に記録を行うインクジェット記録方法において、マゼンタインクとして（６）から（８）のいずれか一項に記載の水性マゼンタインク組成物を使用することを特徴とするインクジェット記録方法、
（１２）被記録材が情報伝達用シートである（１１）に記載のインクジェット記録方法、
（１３）情報伝達用シートが表面処理されたシートである（１２）に記載のインクジェット記録方法、
（１４）（１）から（５）のいずれか１項に記載のモノアゾ化合物またはその塩、又は（６）から（８）のいずれか１項に記載の水性マゼンタインク組成物で着色された着色体
（１５）着色がプリンタによりなされた（１４）の着色体、
（１６）（６）から（８）のいずれか１項に記載の水性マゼンタインク組成物を含む容器が装填されたインクジェットプリンタ、
に関する。
尚、本発明において断りが無いかぎりスルホン酸基及びカルボキシル基は遊離酸の形で表す。
【０００５】
【発明の実施の形態】
本発明を詳細に説明する。
【０００６】
式（１）のＸ、Ｙは置換もしくは非置換のアミノ基、置換もしくは非置換の水酸基、置換もしくは非置換のメルカプト基を表す。
置換もしくは非置換のアミノ基としては、例えばアミノ基；置換もしくは非置換のアニリノ基；置換もしくは非置換のピリジニウム基；置換もしくは非置換のベンジルアミノ基；置換基としてカルボキシル基、スルホン酸基、水酸基、炭素数１〜４のアルコキシ基を１〜２個有してもよいアルキルアミノ基；炭素数１〜４のアルコキシ基を１〜２個有してもよいジアルキルアミノ基、モルホリノ基、アリルアミノ基、ジアリルアミノ基；置換もしくは非置換の第４級アンモニウム基；シクロヘキシルアミノ基等があげられる。
置換もしくは非置換の水酸基としては、例えば水酸基；炭素数１〜４のアルコキシ基；置換もしくは非置換のフェノキシ基、ベンジルオキシ基、シクロヘキシルオキシ基等があげられる。置換もしくは非置換のメルカプト基としては、例えばメルカプト基、炭素数１〜６のアルキルメルカプト基；ヒドロキシ基、シアノ基、アルコキシ基、ヒドロキシアルコキシ基、スルホン酸基、またはカルボキシル基で置換されていてもよい炭素数１〜６アルキルメルカプト基が挙げられ、スルホン酸基で置換された炭素数１〜４アルキルメルカプト基が好ましい。
【０００７】
式（１）のＸ、Ｙにおいて置換もしくは非置換のアニリノ基の例は、アニリノ基、２−メチルアニリノ基、４−ブチルアニリノ基、４−オクチルアニリノ基、３−スルホアニリノ基、４−スルホアニリノ基、２，５−ジスモロホアニリノ基、２−カルボキシアニリノ基、３，５−ジカルボキシアニリノ基、４−ヒドロキシ−３−カルボキシアニリノ基、４−ヒドロキシ−５−カルボキシアニリノ基等である。置換もしくは非置換のピリジニウム基の例は、３−カルボキシピリジニウム基、４−メチルピリジニウム基、３−カルバモイルピリジニウム基、４−スルホピリジニウム基等である。置換もしくは非置換のベンジルアミノ基の例は、ベンジルアミノ基、４−メチルベンジルアミノ基、４−クロルベンジルアミノ基等である。置換基としてカルボキシル基、スルホン酸基、水酸基、炭素数１〜４のアルコキシ基を１〜２個有してもよいアルキルアミノ基やジアルキルアミノ基の例は、ジメチルアミノ基、エチルアミノ基、ｎ−ブチルアミノ基、オクチルアミノ基、２−スルホエチルアミノ基、カルボキシメチルアミノ基、ジ（カルボキシメチル）アミノ基、１，２−ジカルボキシプロピルアミノ基、２−ヒドロキシエチルアミノ基、ジ（２−ヒドロキシエチル）アミノ基、２−ヒドロキシプロピルアミノ基等である。置換もしくは非置換の第４級アンモニウム基の例は、トリメチルアミノ基、トリエチルアミノ基、１，４−ジアザビシクロ−（２，２，２）−オクタン基等である。
炭素数１〜４のアルコキシ基の例は、メトキシ基、エトキシ基、イソプロポキシ基、ｎ−ブトキシ基等である。置換もしくは非置換のフェノキシ基の例はフェノキシ基、２−カルボキシフェノキシ基、４−カルボキシフェノキシ基、３−メチルフェノキシ基、４−スルホフェノキシ基等である。
好ましいＸ、Ｙとしては、モルホリノ基、水酸基、２−メチルアニリノ基、３−スルホアニリノ基、３，５−ジカルボキシアニリノ基、４−ヒドロキシ−５−カルボキシアニリノ基、３−カルボキシピリジニウム基、カルボキシメチルアミノ基、ジ（カルボキシメチル）アミノ基、フェノキシ基、２−カルボキシフェノキシ基、スルホプロピルメルカプト基、スルホエチルアミノ基であり、さらに好ましくは、水酸基、３，５−ジカルボキシアニリノ基、４−ヒドロキシ−５−カルボキシアニリノ基、スルホプロピルメルカプト基、スルホエチルアミノ基である。
【０００８】
式（１）においてＲは置換または非置換のフェニル基、メチル基、フェニルアセチル基、またはフェノキシアセチル基を表し、フェニル基の置換基としてはメチル基、エチル基、ｎ−プロピル基、ｉ−プロピル基、ｎ−ブチル基、ｉ−ブチル基、第３ブチル基等のアルキル基が好ましい。
好ましいＲとしては、フェニル基、４−メチルフェニル基、フェニルアセチル基、またはフェノキシアセチル基があげられ、更に好ましくはフェニル基である。Ａは水素原子または置換基を表すが、水素原子、スルホン酸基、カルボン酸基が好ましく、スルホン酸が特に好ましい。好ましい置換位置は後記する式（８）における４位である。また、ナフタレン環上のスルホン酸の位置は後記する式（８）における４位、３位が好ましく、３位が特に好ましい。
【０００９】
本発明の式（１）の化合物の塩は、無機または有機陽イオンの塩である。適当な無機塩は、特にアルカリ金属塩およびアルカリ土類金属塩である。好ましい無機塩としては、リチウムおよびナトリウムの塩であり、適当な有機塩としては、式（２）で表されるアンモニウム塩があげられる。
【００１０】
式（２）のＸ１〜Ｘ４においてアルキル基の例は前記と同じものであり、ヒドロキシ−アルキル基の例はヒドロキシメチル基、ヒドロキシエチル基、３−ヒドロキシプロピル基、２−ヒドロキシプロピル基、４−ヒドロキシブチル基、３−ヒドロキシブチル基、２−ヒドロキシブチル基等であり、ヒドロキシエトキシ−アルキル基の例はヒドロキシエトキシメチル基、２−ヒドロキシエトキシエチル基、３−ヒドロキシエトキシプロピル基、２−ヒドロキシエトキシプロピル基、４−ヒドロキシエトキシブチル基、３−ヒドロキシエトキシブチル基、２−ヒドロキシエトキシブチル基等である。
【００１１】
式（２）のアンモニウム塩の具体例を表１に示す。
【００１２】
式（１）で表されるモノアゾ化合物は、例えば次のようにして製造する事が出来る。例えば塩化シアヌルと式（５）
【００１４】
【化１５】
（式中、Ａ、ｍは前記と同じ意味を有する）で表される化合物を１次縮合させることにより得られる化合物を常法によりジアゾ化し、式（６）
【００１６】
【化１６】
又、塩化シアヌルとの１次縮合反応は、好ましくは水溶媒中通常０−２０℃、好ましくは５−１０℃、ｐＨ１−９好ましくはｐＨ１−５において、又２次縮合反応は、通常１０−６０℃、好ましくは２０−５０℃、ｐＨ２−１１、好ましくは４−１０において、更に３次縮合反応は、通常６０−１００℃、好ましくは７０−９５℃、ｐＨ２−１２、好ましくは４−１０において、それぞれ実施される。
又、式（１）で表される化合物は、次の方法によっても製造することが出来る。即ち、塩化シアヌルと式（３）で表される化合物を１次縮合させ、更に式Ｘ−Ｈで表される化合物と２次縮合させることにより得られる化合物を常法によりジアゾ化し、式（４）で表される化合物とカップリングさせた後、更に式Ｙ−Ｈで表される化合物と３次縮合させるか、式Ｘ−Ｈで表される化合物を２次縮合させた後、更に式Ｙ−Ｈで表される化合物と３次縮合させた後、常法によりジアゾ化し、式（４）表される化合物とカップリングさせることによっても式（１）で表される水溶性モノアゾ化合物を得ることができる。
尚、例えば、特許文献１０に、本発明の式（１）で表されるモノアゾ化合物の前駆体に相当する式（７）
【００１７】
【化１７】
（式（７）中、Ｙ２はハロゲン原子を表す）で表される化合物についての製法が記載されている。
【００１９】
前記式（１）に示した化合物の好適な例として、特に限定されるものではないが、具体的には下記表１及び２のような構造が挙げられる。
尚、表１において便宜上、下記式（８）のようにＡ、Ｒ、スルホン酸の置換位置を定義する。
【００２０】
【化１８】
【表１】
【表２】
最終的に、本発明による式（１）で表されるモノアゾ化合物またはその塩（以下断りの無い限りモノアゾ化合物またはその塩を単にモノアゾ化合物と記す。）は、鉱酸の添加により遊離酸の形で単離する事ができ、これから水または酸性化した水による洗浄により無機塩を除去する事が出来る。次に、この様に得られる低い塩含有率を有する酸型色素は、水性媒体中で水酸化物および／または炭酸塩、例えば水酸化リチウム、炭酸リチウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウムまたは前記一般式（２）で表されるアミンにより中和することにより対応する塩の溶液とすることが出来る。好ましいアミンとしては、例えばアンモニア、エタノールアミン、ジエタノールアミン、トリエタノールアミン、Ｎ−メチル−Ｎ−エタノールアミン、Ｎ−メチル−Ｎ，Ｎ−ジエタノールアミン、２−（２−ヒドロキシエトキシ）−エチルアミン、ジ［２−（２−ヒドロキシエトキシ）エチル］アミン、トリ［２−（２−ヒドロキシエトキシ）エチル］アミン等があげられる。
【００２４】
式（１）で表されるモノアゾ化合物は、天然及び合成繊維材料との混紡品の染色に適しており、さらにはこれら染料は、筆記用インクおよび記録用液の製造に著しく適している。
【００２５】
式（１）で表される本発明のモノアゾ化合物の反応液は、記録用インク組成物の製造に直接使用する事が出来る。しかし、これを反応液から単離し、乾燥、例えばスプレー乾燥させ、次にインク組成物に加工することもできる。最終製品の記録用インク組成物は、式（１）で表される本発明のモノアゾ化合物を水溶液中に通常０．１〜２０重量％、より好ましくは１〜１５重量％、更に好ましくは２〜１０重量％程度含有する。本発明のインク組成物には、水溶性有機溶剤０〜３０重量％、インク調製剤０〜５重量％含有していても良い。
【００２６】
本発明の水性マゼンタインク組成物は、式（１）で表されるモノアゾ化合物を水または水性溶媒（水溶性有機溶剤含有水）に溶解したものである。
【００２７】
本発明で使用しうる水溶性有機溶剤としては、例えばメタノール、エタノール、プロパノール、イソプロパノール、ブタノール、イソブタノール、第二ブタノール、第三ブタノール等のＣ１〜Ｃ４アルカノール、Ｎ，Ｎ−ジメチルホルムアミドまたはＮ，Ｎ−ジメチルアセトアミド等のカルボン酸アミド、２−ピロリドン、Ｎ−メチルピロリジン−２−オン等のラクタム、１，３−ジメチルイミダゾリジン−２−オンまたは１，３−ジメチルヘキサヒドロピリミド−２−オン等の環式尿素類、アセトン、メチルエチルケトン、２−メチル−２−ヒドロキシペンタン−４−オン等のケトンまたはケトアルコール、テトラヒドロフラン、ジオキサン等の環状エーテル、エチレングリコール、１，２−または１，３−プロピレングリコール、１，２−または１，４−ブチレングリコール、１，６−ヘキシレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ジプロピレングリコール、チオジグリコール、ポリエチレングリコール、ポリプロピレングリコール等の（Ｃ２〜Ｃ６）アルキレン単位を有するモノマー、オリゴマーまたはポリアルキレングリコールまたはチオグリコール、グリセリン、ヘキサン−１．２．６−トリオール等のポリオール（トリオール）、エチレングリコールモノメチルエーテルまたはエチレングリコールモノエチルエーテル、ジエチレングリコールモノメチルエーテル又はジエチレングリコールモノエチルエーテル又はトリエチレングリコールモノメチルエーテル又はトリエチレングリコールモノエチルエーテル等の多価アルコールの（Ｃ１〜Ｃ４）アルキルエーテル、γーブチロラクトンまたはジメチルスルホキシド等があげられる。
【００２８】
本発明の組成物において、水溶性有機溶剤として好ましくは２−ピロリドン、Ｎ−メチルピロリジン−２−オン、モノ、ジまたはトリエチレングリコール、ジプロピレングリコールであり、より好ましくは２−ピロリドン、Ｎ−メチルピロリジン−２−オン、ジエチレングリコールである。
【００２９】
インク調製剤としては、例えば防腐防黴剤、ｐＨ調整剤、キレート試薬、防錆剤、水溶性紫外線吸収剤、水溶性高分子化合物、染料溶解剤、界面活性剤などがあげられる。防腐防黴剤としては、例えば無水酢酸ソーダ、ソルビン酸ソーダ、２−ピリジンチオール−１−オキサイドナトリウム、安息香酸ナトリウム、ペンタクロロフェノールナトリウム、１，２−ベンゾイソチアゾリン−３−オン等があげられる。ｐＨ調整剤としては、調合されるインクに悪影響を及ぼさずに、インクのｐＨを８．０〜１１．０の範囲に制御できるものであれば任意の物質を使用することができる。例えば、ジエタノールアミン、トリエタノールアミンなどのアルカノールアミン、水酸化リチウム、水酸化ナトリウム、水酸化カリウムなどのアルカリ金属の水酸化物、水酸化アンモニウム、あるいは炭酸リチウム、炭酸ナトリウム、炭酸カリウムなどのアルカリ金属の炭酸塩などが挙げられる。キレート試薬としては、例えばエチレンジアミン四酢酸ナトリウム、ニトリロ三酢酸ナトリウム、ヒドロキシエチルエチレンジアミン三酢酸ナトリウム、ジエチレントリアミン五酢酸ナトリウム、ウラミル二酢酸ナトリウムなどがあげられる。防錆剤としては、例えば、酸性亜硫酸塩、チオ硫酸ナトリウム、チオグルコール酸アンモニウム、ジイソプロピルアンモニウムナイトライト、四硝酸ペンタエリスリトール、ジシクロヘキシルアンモニウムナイトライトなどがあげられる。水溶性紫外線吸収剤としては、例えばスルホン化されたベンゾフェノンまたはスルホン化されたベンゾトリアゾール等があげられる。水溶性高分子化合物としては、例えばポリビニルアルコール、セルロース誘導体、ポリアミン、ポリイミン等があげられる。染料溶解剤としては、例えば尿素、ε−カプロラクタム、エチレンカーボネート等があげられる。界面活性剤としては、例えばアニオン界面活性剤、両性界面活性剤、カチオン界面活性剤、ノニオン界面活性剤などがあげられる。アニオン界面活性剤としてはアルキルスリホカルボン酸塩、α−オレフィンスルホン酸塩、ポリオキシエチレンアルキルエーテル酢酸塩、Ｎ−アシルアミノ酸およびその塩、Ｎ−アシルメチルタウリン塩、アルキル硫酸塩ポリオキシアルキルエーテル硫酸塩、アルキル硫酸塩ポリオキシエチレンアルキルエーテル燐酸塩、ロジン酸石鹸、ヒマシ油硫酸エステル塩、ラウリルアルコール硫酸エステル塩、アルキルフェノール型燐酸エステル、アルキル型燐酸エステル、アルキルアリルスルホン塩酸、ジエチルスルホ琥珀酸塩、ジエチルヘキルシルスルホ琥珀酸ジオクチルスルホ琥珀酸塩などが挙げられる。カチオン界面活性剤としては２−ビニルピリジン誘導体、ポリ４−ビニルピリジン誘導体などがある。両性界面活性剤としてはラウリルジメチルアミノ酢酸ベタイン、２−アルキル−Ｎ−カルボキシメチル−Ｎ−ヒドロキシエチルイミダゾリニウムベタイン、ヤシ油脂肪酸アミドプロピルジメチルアミノ酢酸ベタイン、ポリオクチルポリアミノエチルグリシンその他イミダゾリン誘導体などがある。ノニオン界面活性剤としては、ポリオキシエチレンノニルフェニルエーテル、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ドデシルフェニルエーテル、ポリオキシエチレオクチルフェニルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンアルキルエーテル、ポリオキシアリルキルアルキルエーテルなどのエーテル系、ポリオキシエチレンオレイン酸、ポリオキシエチレンオレイン酸エステル、ポリオキシエチレンジステアリン酸エステル、ソルビタンラウレート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタンセスキオレート、ポリオキシエチレンモノオレエート、ポリオキシエチレンステアレートなどのエステル系、２，４，７，９−テトラメチル−５−デシン−４，７−ジオール、３，６−ジメチル−４−オクチン−３，６−ジオール、３，５−ジメチル−１−ヘキシン−３オールなどのアセチレングリコール系（例えば、日信化学社製サーフィノール１０４、１０４Ｅ、１０４ＰＧ５０、８２、４６５、オルフィンＳＴＧなど）、などが挙げられる。これらのインク調製剤は、単独もしくは混合して用いられる。
【００３０】
本発明の水性マゼンタインク組成物は、式（１）で表されるモノアゾ化合物を水または上記水性溶媒（水溶性有機溶剤含有水）に、上記インク調製剤などと共に溶解させることによって製造できる。
この水性マゼンタインク組成物をインクジェットプリンタ用のインクとして使用する場合、モノアゾ化合物としては金属陽イオンの塩化物、硫酸塩等の無機物の含有量が少ないものを用いるのが好ましく、その含有量の目安は例えば１％以下程度である。無機物の少ないモノアゾ化合物を製造するには、例えば逆浸透膜による方法等の通常の方法で、脱塩処理すればよい。
本発明の製造方法において、溶解させる順序には特に制限はない。あらかじめ水または上記水性溶媒（水溶性有機溶剤含有水）に溶解させ、インク調製剤を添加して溶解させてもよいし、式（１）で表されるモノアゾ化合物を水に溶解させたのち、水性溶媒、インク調製剤を添加して溶解させてもよい。またこれと順序が異なっていてもよいし、式（１）で表されるモノアゾ化合物の反応液または逆浸透膜による脱塩処理を行った液に、水性溶媒、インク調製剤を添加してインク組成物を製造してもよい。用いる水はイオン交換水または蒸留水など不純物が少ない物が好ましい。さらに、必要に応じメンブランフィルターなどを用いて精密濾過を行って夾雑物を除いてもよく、インクジェットプリンタ用のインクとして使用する場合は精密濾過を行うことが好ましい。精密濾過を行うフィルターの孔径は１ミクロン〜０．１ミクロン、好ましくは、０．８ミクロン〜０．２ミクロンである。
【００３１】
式（１）で表される化合物を１種以上含有する記録用液は、印捺、複写、マーキング、筆記、製図、スタンピング、または記録法、特にインクジェット印捺法における使用に適する。この場合、水、日光、オゾンおよび摩擦に対する良好な耐性を有する高品質のマゼンタ印捺物が得られる。式（１）で表されるモノアゾ染料に、イエロー、シアン等の染料を配合することによって、マゼンタ色調を好みのものにすることもできる。
【００３２】
本発明の着色体は前記の本発明の化合物で着色されたものである。着色されるべきものとしては、特に制限無く、例えば紙、繊維や布（セルロース、ナイロン、羊毛等）、皮革、カラーフィルター用基材等があげられるがこれらに限定されない。着色法としては、例えば浸染法、捺染法、スクリーン印刷等の印刷法、インクジェットプリンタによる方法等があげられるが、インクジェットプリンタによる方法が好ましい。
【００３３】
本発明のインクジェット記録方法を適用しうる被記録材としては例えば紙、フィルム等の情報伝達用シート、繊維及び皮革等が挙げられる。情報伝達用シートについては、表面処理されたもの、具体的にはこれらの基材にインク受容層を設けたものが好ましい。インク受容層は、例えば上記基材にカチオン系ポリマーを含浸あるいは塗工することにより、また多孔質シリカ、アルミナゾルや特殊セラミックス等インク中の色素を吸収し得る無機微粒子をポリビニルアルコールやポリビニルピロリドン等の親水性ポリマーと共に上記基材表面に塗工することにより設けられる。このようなインク受容層を設けたものは通常インクジェット専用紙（フィルム）あるいは光沢紙（フィルム）と呼ばれ、例えばピクトリコ（旭硝子（株）製）、カラーＢＪペーパー、カラーＢＪフォトフィルムシート（いずれもキャノン（株）製）、カラーイメージジェット用紙（シャープ（株）製）、スーパーファイン専用光沢フィルム（エプソン（株）製）、ピクタファイン（日立マクセル（株）製）等として市販されている。なお、普通紙にも利用できることはもちろんである。
【００３４】
本発明のインクジェット記録方法では、本発明の水性マゼンタインク組成物はイエローインク組成物、シアンインク組成物、必要に応じ、ブラックインク組成物と併用されうる。
各色のインク組成物は、それぞれの容器に注入され、この容器を、本発明の水性マゼンタインク組成物を含有する容器と同様に、インクジェットプリンタの所定位置にセット（装填）されて、使用される。
【００３５】
本発明のインクジェット記録方法で、被記録材に記録するには、例えば上記のインク組成物を含有する容器をインクジェットプリンタの所定位置にセットし、通常の方法で、被記録材に記録すればよい。インクジェットプリンタとしては、例えば機械的振動を利用したピエゾ方式のプリンタや加熱により生ずる泡を利用したバブルジェット（登録商標）方式のプリンタ等があげられる。
【００３６】
本発明の水性インク組成物は、鮮明なマゼンタ色であり、特にインクジェット光沢紙における高い耐光性と耐オゾン性を有する。また、人に対する安全性も高い。他のイエロー、シアンのインクと共に用いる事で、広い可視領域の色調を色出しする事ができ、耐光性及び耐オゾン性に優れたイエロー、シアン、ブラックと共に用いることにより、特に耐オゾン性に優れ、かつ耐光性、耐水性においても優れた記録物を得ることができる。
【００３７】
本発明によるインクは貯蔵中に沈澱、分離することがない。また、本発明によるインクをインクジェット印捺において使用した場合、噴射器を閉塞することもない。本発明によるインクを連続式インクジェットプリンタによる比較的長い時間一定の再循環下またはオンデマンド式インクジェットプリンタによる断続的な使用においても、本発明によるインクの物理的性質は変化しない。
【００３８】
【実施例】
以下に本発明を更に実施例により具体的に説明する。尚、本文中「部」及び「％」とあるのは、特別の記載のない限り重量基準である。
【００３９】
実施例１
常法により、塩化シアヌル１２．９部と２，４−ジアミノベンゼンスルホン酸１３．０部を水性媒体中でｐＨ３−５、温度０−５℃で１次縮合させ、得られた化合物を常法により３５％塩酸２２部と４０％亜硝酸ナトリウム１２．７部でジアゾ化し、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸２９．０部とｐＨ５−６、温度１０−１５℃でカップリングさせた。次いで３，５−ジカルボキシアニリン１２．０部をｐＨ５−６、温度４０−４５℃、４時間で２次縮合させ、更に、ｐＨ９．５−１０．０、温度９０−９５℃、６時間で処理させ、得られた生成物を常法に従い塩析、濾過することにより酸型構造で下記式（９）（化合物例Ｎｏ．９）で表されるモノアゾ化合物（水中でのλｍａｘ＝５１５ｎｍ）を得た。
【００４０】
【化１９】
実施例２
常法により、塩化シアヌル１２．９部と２，４−ジアミノベンゼンスルホン酸１３．０部を水性媒体中でｐＨ３−５、温度０−５℃で１次縮合させ、得られた化合物を常法により３５％塩酸２２部と４０％亜硝酸ナトリウム１２．７部でジアゾ化し、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸２９．０部とｐＨ５−６、温度１０−１５℃でカップリングさせた。次いで３，５−ジカルボキシアニリン１２．０部をｐＨ５−６、温度４０−４５℃、４時間で２次縮合させ、更に４−ヒドロキシー５カルボキシアニリン４２．９部をｐＨ４−５、温度８０−８５℃、４時間で３次縮合させ、得られた生成物を常法に従い塩析、濾過することにより酸型構造で下記式（１０）（化合物例Ｎｏ．１１）で表されるモノアゾ化合物（水中でのλｍａｘ＝５１８ｎｍ）を得た。
【００４２】
【化２０】
実施例３−１２
実施例２において二次縮合で使用した、３，５−ジカルボキシアニリンの変わりに下記表２の第１欄の化合物を、３次縮合で使用した４−ヒドロキシー５カルボキシアニリンの代わりに同表の第２欄の化合物を各々用いて、実施例２と同様の方法で合成すると、各々対応するモノアゾ化合物が得られた。
実施例３では化合物例Ｎｏ．３８、実施例４では化合物例Ｎｏ．１２、実施例５では化合物例Ｎｏ．１３、実施例６では化合物例Ｎｏ．５２、実施例７では化合物例Ｎｏ．５３、実施例８では化合物例Ｎｏ．５４、実施例９では化合物例Ｎｏ．４１、実施例１０では化合物例Ｎｏ．３６、実施例１１では化合物例Ｎｏ．４３、実施例１２では化合物例Ｎｏ．５８がそれぞれ得られた。
【００４４】
実施例１３
実施例１において使用した、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸の代わりに１−ベンゼンスルホニルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸を用いて実施例１と同様の方法で合成すると、酸型構造で下記式（１１）（化合物例Ｎｏ．２８）で表されるモノアゾ化合物が得られた。
【００４６】
【化２１】
実施例１４
実施例１において使用した、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸の代わりに１−ベンゾイルアミノ−８−ヒドロキシナフタレン−４，６−ジスルホン酸を用いて実施例１と同様の方法で合成すると、酸型構造で下記式（１２）（化合物例Ｎｏ．３０）で表されるモノアゾ化合物が得られる。
【００４８】
【化２２】
実施例１５、１６
（Ａ）インクの調製
上記実施例１、３で得られた化合物を用いて表５に示した組成の液体を調製し、０．４５μｍのメンブランフィルターで濾過する事により各インクジェット用水性インク組成物を得た。また水はイオン交換水を使用した。尚、インク組成物のｐＨがｐＨ＝８〜１０、総量１００部になるように水、水酸化ナトリウムを加えた。実施例１で得られた化合物を用いた試験を実施例１５、実施例３で得られた化合物を用いた試験を実施例１６とする。
【００５０】
表５（インク組成）
上記実施例で得られた化合物 ３．０部
水＋水酸化ナトリウム ７７．９部
グリセリン ５．０部
尿素 ５．０部
Ｎ−メチル−２−ピロリドン ４．０部
イソプロピルアルコール ３．０部
ブチルカルビトール ２．０部
サーフィノール１０４ＰＧ５０（日信化学社製） ０．１部
計 １００．０部
【００５１】
（Ｂ）インクジェットプリント
インクジェットプリンタ（商品名 キヤノン社製 ＢＪ−Ｓ６３０）を用いて、普通紙（プリンタペーパーＡ４ ＴＬＢ５Ａ４Ｓ（キャノン社製））、色素受容層を有する光沢紙（エプソン社製ＰＭ写真用紙 ＫＡ４２０ＰＳＫ）の２種にインクジェット記録を行った。
【００５２】
以下比較試験として、実施例１のインクと同じ印字濃度になるようにインクを調製し評価を行った。
比較例１
比較対象として実施例３で得られた化合物の代わりにインクジェット用マゼンタ色素として広く用いられているＣ．Ｉ．ダイレクトレッド２２７（下記式（１３）を２．５部使用する以外は実施例１と同様の組成でインクを調製、インクジェット記録をし、記録画像の評価を行った。
【００５３】
【化２３】
比較例２
比較対象として実施例３で得られた化合物の代わりにインクジェット用マゼンタ色素として広く用いられている特許文献３、化合物Ｎｏ．（１）記載の化合物（下記式（１４）を２部使用する以外は実施例１と同様の組成でインクを調製、インクジェット記録をし、記録画像の評価を行った。
【００５５】
【化２４】
（Ｃ）記録画像の評価
１．色相評価
１−１．光沢紙での色相評価
記録画像の色相、鮮明性：記録紙を測色システム（ＧＲＥＴＡＧ ＳＰＭ５０：ＧＲＥＴＡＧ社製）を用いて測色し、Ｌ＊、ａ＊、ｂ＊値を算出した。色相はＪＮＣ（社団法人 日本印刷産業機械工業会）のＪＡＰＡＮ Ｃｏｌｏｒの標準マゼンタのカラーサンプルとの比較、鮮明性はＣ＊＝（（ａ＊）２＋（ｂ＊）２ ）１／２で評価した。
ＪＮＣのＪＡＰＡＮ Ｃｏｌｏｒの標準マゼンタのカラーサンプルと実施例１５、実施例１６の光沢紙での色相の結果を表６に示す。
【００５７】
表６より、本発明のモノアゾ化合物は、ＪＮＣ標準マゼンタの色相に近く、理想的な色相であることがわかる。
【００５９】
１−２．普通紙での色相評価
上記と同様にして、実施例１５、比較例１、比較例２の普通紙での色相をの結果を表７に示す。
【００６０】
表７より、本発明のモノアゾ化合物は、普通紙に記録画像した色相が、比較例１、２よりＣ＊値が高く、非常に鮮明性が高いことがわかる。
【００６２】
（Ｄ）記録画像のキセノン耐光性試験
光沢紙にプリントした試験片をキセノンウェザオメーターＣｉ４０００（ＡＴＬＡＳ社製）を用い、０．３６Ｗ／平方メートルの照度で５０時間照射し、試験前後の色差（ΔＥ）と残存濃度（％）（試験前の濃度／試験後の濃度×１００）を測定した。結果は表８に示す。
（Ｅ）記録画像のオゾン耐性試験
光沢紙にプリントした試験片を、加湿器をオゾンウェザーメーター内に導入し、湿度６０％を保持させたオゾンウェザーメーター（スガ試験機社製 型式ＯＭＳ−Ｈ）を用い、温度約３５℃、オゾン濃度１２ｐｐｍで２時間放置し、試験前後の色差（ΔＥ）と残存濃度（％）（試験後の濃度／試験前の濃度×１００）を測定した。結果は表８に示す。
【００６３】
（Ｆ）記録画像の耐湿性試験
光沢紙にプリントした試験片を、恒温恒湿器（応用技研産業社製）を用いて５０℃、９０％ＲＨで７日間放置し、試験前後の染料の滲みを目視により判定した。
○ 染料に滲みがほとんど見られない。
△ 染料のにじみがやや見られる。
× 染料の滲みがかなり見られる。
【００６４】
表８より、実施例１５は、比較例１より耐光性、オゾン耐性が強く、比較例２よりオゾン耐性、耐湿性が強いことがわかる。比較例１６は耐光性、オゾン耐性、が比較例１，２より強く、耐湿性は比較例２より強いことがわかる。
本発明のモノアゾ化合物を用いたマゼンタインクは、色相、耐光堅牢度、耐オゾン堅牢度、耐湿性が総合的に強い、非常に優れたマゼンタ色インクであることがわかる。
【００６６】
実施例１７
常法により、塩化シアヌル１８．８部と２，４−ジアミノベンゼンスルホン酸１８．８部を水性媒体中でｐＨ３−６、温度０−５℃で１次縮合させ、得られた化合物を常法により、塩酸と亜硝酸ナトリウムでジアゾ化し、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸４３．６部とｐＨ７−８、温度５−１０℃でカップリングさせた。次いで５−アミノイソフタル酸１８．１部をｐＨ５−６、温度４０−５０℃で２次縮合させ、更に３−メルカプト−１−プロパンスルホン酸ナトリウム２６．７部を加えｐＨ８−１０、温度８５−９５℃で３次縮合を行なった。得られた生成物を常法に従い塩析、濾過することにより、酸型構造で下記式（１６）（化合物例Ｎｏ．６１）で表されるモノアゾ化合物（水中でのλｍａｘ＝５１７ｎｍ）を得た。
【００６７】
【化２５】
実施例１８
常法により、塩化シアヌル１８．８部と２，４−ジアミノベンゼンスルホン酸１８．８部を水性媒体中でｐＨ３−６、温度０−５℃で１次縮合させ、得られた化合物を常法により、塩酸と亜硝酸ナトリウムでジアゾ化し、１−ベンゾイルアミノ−８−ヒドロキシナフタレン−３，６−ジスルホン酸４３．６部とｐＨ７−８、温度５−１０℃でカップリングさせた。次いで５−アミノイソフタル酸１８．１部をｐＨ５−６、温度４０−５０℃で２次縮合させ、更にタウリン１８．７部を加えｐＨ７−９、温度８５−９５℃で３次縮合を行なった。得られた生成物を常法に従い塩析、濾過することにより酸型構造で下記式（１６）（化合物例Ｎｏ．６３）で表されるモノアゾ化合物（水中でのλｍａｘ＝５２０ｎｍ）を得た。
【化２６】
実施例１９、２０
（Ａ）インクの調製
上記実施例１７で得られた化合物を２．８部使用する以外は実施例１５における表５と同様のインク組成でインクを調製し、前記（Ｂ）と同様にしてインクジェット記録をし、記録画像の評価を行った。これを実施例１９とする。
実施例１８で得られた化合物を３．３部使用する以外は実施例１５における表５と同様のインク組成でインクを調製し、前記（Ｂ）と同様にしてインクジェット記録をし、記録画像の評価を行った。これを実施例２０とする。
【００７０】
前記の（Ｃ）記録画像の評価、１．色相評価、１−２．普通紙での色相評価と同様にして記録画像の色相、鮮明性を測定した。結果を表９に示す。
【００７１】
表９より、本発明のアゾ化合物は、普通紙に記録画像した色相が、比較例１、２よりＣ＊値が高く、非常に鮮明性が高いことがわかる。
【００７３】
前記、（Ｅ）記録画像のオゾン耐性試験、（Ｆ）記録画像の耐湿性試験と同様にして記録画像のオゾン耐性試験、耐湿性試験行った。その結果を表１０に示す。
【００７４】
表１０より、実施例１９、２０は、比較例２よりオゾン耐性、耐湿性が強いことがわかる。
本発明のモノアゾ化合物を用いたマゼンタインクは、色相、耐光堅牢度、耐オゾン堅牢度、耐湿性が総合的に強い、非常に優れたマゼンタ色インクであることがわかる。
【００７６】
【発明の効果】
本発明の化合物は水溶解性に優れ、インク組成物製造過程でのメンブランフィルターに対するろ過性が良好という特徴を有する。又、この化合物を使用した本発明のインク組成物は長期間保存後の結晶析出、物性変化、色変化等もなく、貯蔵安定性が良好である。そして本発明のインク組成物をインクジェット記録用のマゼンタインクとして使用した印刷物はメディア（紙、フィルム等）を選択することなく理想的なマゼンタの色相である。また耐光性、オゾン耐性にも非常に優れている。更に本発明のマゼンタインク組成物は、イエロー、シアン及びブラックインクと共に用いることで耐光性、オゾン耐性などに優れたインクジェット記録が可能である。従って、本発明の化合物はインクジェット記録用のマゼンタインクとして極めて有用である。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a water-soluble monoazo compound, an aqueous magenta ink composition, and a colored body.
[0002]
[Prior art]
Among various color recording methods, various ejection methods of ink have been developed in a recording method using an ink-jet printer, which is one of the representative methods. The recording is performed by adhering to a recording material (paper, film, cloth, etc.). This is because the recording head and the recording material do not come in contact with each other, so that there is no sound and it is quiet, and because of its features such as miniaturization, high speed, and easy colorization, it has been spreading rapidly in recent years, and will continue to be used in the future. Large growth is expected. Among them, when an image or character information on a color display of a computer is recorded in color by an ink jet printer, it is generally expressed by subtractive color mixture using four inks of yellow, magenta, cyan and black. In order to faithfully reproduce an additive color image by R, G, and B such as a CRT display as a subtractive color image, the hue and sharpness of the ink used are important. In addition, the ink composition is required to be stable for long-term storage, to have a high density of a printed image, and to be excellent in fastness such as water resistance, light resistance and ozone resistance.
Ozone gas resistance refers to resistance to a phenomenon in which ozone gas having an oxidizing effect existing in air reacts with a dye in recording paper to cause discoloration of a printed image. This ozone gas is considered to be the biggest factor that is believed to promote the fading phenomenon of the ink jet recorded image. Since this discoloration and fading phenomenon is characteristic of an ink jet image, improvement of ozone gas resistance is an important issue. In particular, most ink-receiving layers provided on the surface of photographic-quality inkjet paper use a porous inorganic material in order to accelerate drying of the ink and reduce bleeding with high image quality. Discoloration and fading due to ozone gas are remarkably observed on such recording paper.
In the future, when used in exhibitions such as advertisements in order to expand the fields of use of ink-based printing methods, they will often be exposed to light (electric lights, fluorescent lights, sunlight, etc.). In addition to water resistance, light resistance, and moisture resistance, there has been a strong demand for the ink composition to be used and the colored body colored with the ink composition, particularly, ozone gas resistance.
To solve these problems, many applications such as Patent Documents 1 to 9 have been filed, but have not yet completely satisfied the market requirements.
[Patent Document 1]
JP-A-4-279671
[Patent Document 2]
JP-A-6-329933
[Patent Document 3]
JP-A-8-73791
[Patent Document 4]
JP-A-8-113745
[Patent Document 5]
JP-A-10-46045
[Patent Document 6]
JP-A-10-329403
[Patent Document 7]
JP-A-11-158429
[Patent Document 8]
JP 2000-265099 A
[Patent Document 9]
JP 2001-72886 A
[Patent Document 10]
Japanese Patent Publication No. 35-12784
[0003]
[Problems to be solved by the invention]
The present invention has high solubility in water, is stable even when stored for a long time, has a high density of printed images, and has excellent ozone resistance, light resistance, and water resistance, and is more safe for humans. It is an object of the present invention to provide a water-soluble monoazo compound having a high magenta color and an ink composition containing the same.
[0004]
[Means for Solving the Problems]
The present inventors have conducted intensive studies to solve the above-described problems, and as a result, have reached the present invention. That is, the present invention
(1) The following equation (1)
Embedded image
(2) The following equation (1)
Embedded image
(3) The salt is a lithium salt, a sodium salt, a potassium salt or a compound of the formula (2)
Embedded image
(4) In the formula (1), X and Y each independently represent an amino group; a substituted or unsubstituted anilino group; a substituted or unsubstituted pyridinium group; a substituted or unsubstituted benzylamino group; A sulfonic acid group, a hydroxyl group, a cyano group, an alkoxy group having 1 to 4 carbon atoms, an alkylamino group which may have 1 to 2 alkoxy groups having 1 to 4 carbon atoms; Optionally substituted dialkylamino group, morpholino group, allylamino group, diallylamino group; substituted or unsubstituted quaternary ammonium group; cyclohexylamino group; hydroxyl group; alkoxy group having 1 to 4 carbon atoms; substituted or unsubstituted Phenoxy, benzyloxy, cyclohexyloxy groups; hydroxy, cyano, alkoxy, hydroxyalkoxy An alkylmercapto group which may be substituted with a sulfonic group, a sulfonic group, or a carboxyl group, A is a sulfonic group, B is -CO, R is a phenyl group, a phenylacetyl group, a phenoxyacetyl group, and m is 1. The monoazo compound or a salt thereof according to any one of (1) to (3),
(5) In the formula (1), each of X and Y independently represents an amino group; and has, as a substituent, one or two alkyl groups having 1 to 8 carbon atoms, a sulfonic acid group, a carboxyl group, a hydroxyl group, and a mohololino group. Anilino group, pyridinium group; benzylamino group; having 1 to 2 carboxyl groups, sulfonic acid groups, hydroxyl cyano groups, alkoxy groups having 1 to 4 carbon atoms, and alkoxy groups having 1 to 4 carbon atoms C1-C6 alkylamino group; C1-C4 alkoxy group alkylamino group; Dialkylamino group which may have 1-2 C1-C4 alkoxy group, morpholino group, allylamino Group, diallylamino group; quaternary ammonium which may have an alkyl group having 1 to 4 carbon atoms and 1,4-diazabicyclo- (2,2,2) -octane group as a substituent A cyclohexylamino group; a hydroxyl group; an alkoxy group having 1 to 4 carbon atoms; an alkyl group having 1 to 8 carbon atoms, a sulfonic acid group, a phenoxy group which may have a carboxyl group, a benzyloxy group, and a cyclohexyloxy group. Group; a hydroxy group, a cyano group, an alkoxy group, a hydroxyalkoxy group, a sulfonic acid group, or an alkylmercapto group having 1 to 6 carbon atoms which may be substituted with a carboxyl group, A is a sulfonic acid group, B is -CO, R Is a phenyl group, and m is 1. The monoazo compound or a salt thereof according to any one of (1) to (4),
(6) The following formula (3) is used as the skeleton.
Embedded image
(7) Formula (4) below as a skeleton
Embedded image
(8) An aqueous magenta ink composition comprising the monoazo compound or a salt thereof according to any one of (1) to (5).
(9) The following formula (3) is used as the skeleton.
Embedded image
(10) The following formula (4) is used as a skeleton.
Embedded image
(11) In an ink jet recording method for performing recording on a recording material by discharging ink droplets according to a recording signal, the aqueous magenta ink composition according to any one of (6) to (8) is used as a magenta ink. Inkjet recording method characterized by using,
(12) The inkjet recording method according to (11), wherein the recording material is an information transmission sheet.
(13) The inkjet recording method according to (12), wherein the information transmission sheet is a surface-treated sheet,
(14) coloring with the monoazo compound or a salt thereof according to any one of (1) to (5) or the aqueous magenta ink composition according to any one of (6) to (8) body
(15) the colored body of (14), wherein the colored body is colored by a printer;
(16) An inkjet printer loaded with a container containing the aqueous magenta ink composition according to any one of (6) to (8),
About.
In the present invention, unless otherwise specified, sulfonic acid groups and carboxyl groups are expressed in the form of free acids.
[0005]
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention will be described in detail.
[0006]
X and Y in the formula (1) represent a substituted or unsubstituted amino group, a substituted or unsubstituted hydroxyl group, and a substituted or unsubstituted mercapto group.
Examples of the substituted or unsubstituted amino group include an amino group; a substituted or unsubstituted anilino group; a substituted or unsubstituted pyridinium group; a substituted or unsubstituted benzylamino group; An alkylamino group which may have 1 to 2 alkoxy groups having 1 to 4 carbon atoms; a dialkylamino group, a morpholino group, an allylamino group which may have 1 or 2 alkoxy groups having 1 to 4 carbon atoms A substituted or unsubstituted quaternary ammonium group; a cyclohexylamino group.
Examples of the substituted or unsubstituted hydroxyl group include a hydroxyl group; an alkoxy group having 1 to 4 carbon atoms; a substituted or unsubstituted phenoxy group, a benzyloxy group, and a cyclohexyloxy group. Examples of the substituted or unsubstituted mercapto group include a mercapto group, an alkyl mercapto group having 1 to 6 carbon atoms; and a hydroxy group, a cyano group, an alkoxy group, a hydroxyalkoxy group, a sulfonic acid group, or a carboxyl group. Examples thereof include a C1-6 alkylmercapto group, and a C1-4 alkylmercapto group substituted with a sulfonic acid group is preferable.
[0007]
Examples of the substituted or unsubstituted anilino group in X and Y of the formula (1) include an anilino group, a 2-methylanilino group, a 4-butylanilino group, a 4-octylanilino group, a 3-sulfoanilino group, a 4-sulfoanilino group, 2,5-dismolofoanilino group, 2-carboxyanilino group, 3,5-dicarboxyanilino group, 4-hydroxy-3-carboxyanilino group, 4-hydroxy-5-carboxyanilino group, etc. It is. Examples of the substituted or unsubstituted pyridinium group include a 3-carboxypyridinium group, a 4-methylpyridinium group, a 3-carbamoylpyridinium group, a 4-sulfopyridinium group, and the like. Examples of the substituted or unsubstituted benzylamino group include a benzylamino group, a 4-methylbenzylamino group and a 4-chlorobenzylamino group. Examples of a carboxyl group, a sulfonic acid group, a hydroxyl group, an alkylamino group or a dialkylamino group which may have 1 to 2 alkoxy groups having 1 to 4 carbon atoms as a substituent include a dimethylamino group, an ethylamino group and n -Butylamino group, octylamino group, 2-sulfoethylamino group, carboxymethylamino group, di (carboxymethyl) amino group, 1,2-dicarboxypropylamino group, 2-hydroxyethylamino group, di (2- (Hydroxyethyl) amino group, 2-hydroxypropylamino group and the like. Examples of the substituted or unsubstituted quaternary ammonium groups include a trimethylamino group, a triethylamino group, a 1,4-diazabicyclo- (2,2,2) -octane group and the like.
Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, an isopropoxy group and an n-butoxy group. Examples of the substituted or unsubstituted phenoxy group include a phenoxy group, a 2-carboxyphenoxy group, a 4-carboxyphenoxy group, a 3-methylphenoxy group, and a 4-sulfophenoxy group.
Preferred X and Y are morpholino group, hydroxyl group, 2-methylanilino group, 3-sulfoanilino group, 3,5-dicarboxyanilino group, 4-hydroxy-5-carboxyanilino group, 3-carboxypyridinium group, carboxy A methylamino group, a di (carboxymethyl) amino group, a phenoxy group, a 2-carboxyphenoxy group, a sulfopropylmercapto group, and a sulfoethylamino group, more preferably a hydroxyl group, a 3,5-dicarboxyanilino group, -Hydroxy-5-carboxyanilino group, sulfopropylmercapto group and sulfoethylamino group.
[0008]
In the formula (1), R represents a substituted or unsubstituted phenyl group, methyl group, phenylacetyl group, or phenoxyacetyl group, and the substituent of the phenyl group is a methyl group, an ethyl group, an n-propyl group, an i-propyl group. And alkyl groups such as n-butyl group, i-butyl group and tertiary butyl group.
Preferred R is a phenyl group, a 4-methylphenyl group, a phenylacetyl group, or a phenoxyacetyl group, and more preferably a phenyl group. A represents a hydrogen atom or a substituent, but is preferably a hydrogen atom, a sulfonic acid group, or a carboxylic acid group, and particularly preferably sulfonic acid. A preferred substitution position is the 4-position in the formula (8) described later. Further, the position of the sulfonic acid on the naphthalene ring is preferably the 4-position and the 3-position in the formula (8) described below, and particularly preferably the 3-position.
[0009]
The salts of the compounds of the formula (1) according to the invention are salts of inorganic or organic cations. Suitable inorganic salts are, in particular, alkali metal salts and alkaline earth metal salts. Preferred inorganic salts are lithium and sodium salts, and suitable organic salts include ammonium salts represented by formula (2).
[0010]
X in equation (2) 1 ~ X 4 In the above, examples of the alkyl group are the same as described above, and examples of the hydroxy-alkyl group include a hydroxymethyl group, a hydroxyethyl group, a 3-hydroxypropyl group, a 2-hydroxypropyl group, a 4-hydroxybutyl group, and a 3-hydroxybutyl And 2-hydroxybutyl groups, and examples of hydroxyethoxy-alkyl groups include hydroxyethoxymethyl, 2-hydroxyethoxyethyl, 3-hydroxyethoxypropyl, 2-hydroxyethoxypropyl, and 4-hydroxyethoxybutyl. Group, 3-hydroxyethoxybutyl group, 2-hydroxyethoxybutyl group and the like.
[0011]
Table 1 shows specific examples of the ammonium salt of the formula (2).
[0012]
The monoazo compound represented by the formula (1) can be produced, for example, as follows. For example, cyanuric chloride and formula (5)
[0014]
Embedded image
(Wherein, A and m have the same meanings as described above), and the compound obtained by primary condensation of the compound represented by the formula (6)
[0016]
Embedded image
The primary condensation reaction with cyanuric chloride is preferably carried out in an aqueous solvent usually at 0-20 ° C., preferably 5-10 ° C., pH 1-9, preferably pH 1-5. At 60 ° C., preferably 20-50 ° C., pH 2-11, preferably 4-10, the tertiary condensation reaction is usually 60-100 ° C., preferably 70-95 ° C., pH 2-12, preferably 4-10. , Respectively.
The compound represented by the formula (1) can also be produced by the following method. That is, the compound obtained by subjecting cyanuric chloride to the compound represented by the formula (3) to undergo primary condensation and further subjecting the compound represented by the formula XH to secondary condensation is diazotized by a conventional method to obtain a compound represented by the formula (4) ), And then tertiary condensed with the compound represented by the formula YH, or secondarily condensed with the compound represented by the formula XH, and then further condensed with the compound represented by the formula Y After tertiary condensation with the compound represented by -H, diazotization is carried out by a conventional method, and coupling with the compound represented by the formula (4) yields a water-soluble monoazo compound represented by the formula (1). be able to.
Incidentally, for example, Patent Document 10 discloses a compound of the formula (7) corresponding to the precursor of the monoazo compound represented by the formula (1) of the present invention.
[0017]
Embedded image
(In the equation (7), Y 2 Represents a halogen atom).
[0019]
Preferable examples of the compound represented by the formula (1) are not particularly limited, but specific examples include the structures shown in Tables 1 and 2 below.
In Table 1, for the sake of convenience, substitution positions of A, R and sulfonic acid are defined as in the following formula (8).
[0020]
Embedded image
[Table 1]
[Table 2]
Finally, the monoazo compound represented by the formula (1) or a salt thereof (hereinafter the monoazo compound or a salt thereof is simply referred to as a monoazo compound unless otherwise specified) according to the present invention is converted into a free acid form by addition of a mineral acid. The inorganic salts can be removed therefrom by washing with water or acidified water. The acid dyes having a low salt content obtained in this way can then be used in aqueous media in the form of hydroxides and / or carbonates such as lithium hydroxide, lithium carbonate, sodium hydroxide, sodium carbonate, potassium carbonate or By neutralizing with the amine represented by the general formula (2), a solution of the corresponding salt can be obtained. Preferred amines include, for example, ammonia, ethanolamine, diethanolamine, triethanolamine, N-methyl-N-ethanolamine, N-methyl-N, N-diethanolamine, 2- (2-hydroxyethoxy) -ethylamine, di [2 -(2-hydroxyethoxy) ethyl] amine, tri [2- (2-hydroxyethoxy) ethyl] amine and the like.
[0024]
The monoazo compound represented by the formula (1) is suitable for dyeing a blended product with natural and synthetic fiber materials, and these dyes are extremely suitable for producing writing inks and recording liquids.
[0025]
The reaction solution of the monoazo compound of the present invention represented by the formula (1) can be directly used for producing a recording ink composition. However, it can also be isolated from the reaction liquid, dried, for example spray dried, and then processed into an ink composition. The recording ink composition of the final product contains the monoazo compound of the present invention represented by the formula (1) in an aqueous solution in an amount of usually 0.1 to 20% by weight, preferably 1 to 15% by weight, more preferably 2 to 15% by weight. It contains about 10% by weight. The ink composition of the present invention may contain 0 to 30% by weight of a water-soluble organic solvent and 0 to 5% by weight of an ink preparation.
[0026]
The aqueous magenta ink composition of the present invention is obtained by dissolving the monoazo compound represented by the formula (1) in water or an aqueous solvent (water containing a water-soluble organic solvent).
[0027]
Examples of the water-soluble organic solvent that can be used in the present invention include C1-C4 alkanols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, sec-butanol and tert-butanol, N, N-dimethylformamide or N, N-dimethylformamide. Carboxylic acid amides such as N-dimethylacetamide; lactams such as 2-pyrrolidone and N-methylpyrrolidin-2-one; 1,3-dimethylimidazolidin-2-one or 1,3-dimethylhexahydropyrimido-2- Cyclic ureas such as on, ketones or keto alcohols such as acetone, methyl ethyl ketone, 2-methyl-2-hydroxypentan-4-one, cyclic ethers such as tetrahydrofuran and dioxane, ethylene glycol, 1,2- or 1,3 -Propylene glycol, 1,2 Or (C2 to C6) alkylene units such as 1,4-butylene glycol, 1,6-hexylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, thiodiglycol, polyethylene glycol, and polypropylene glycol. Monomer, oligomer or polyalkylene glycol or thioglycol, glycerin, polyol (triol) such as hexane-1.2.6-triol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, diethylene glycol monomethyl ether or diethylene glycol monoethyl ether or triethylene glycol Such as ethylene glycol monomethyl ether or triethylene glycol monoethyl ether (C1 -C4) alkyl ethers of polyhydric alcohols, gamma-butyrolactone or dimethyl sulfoxide and the like.
[0028]
In the composition of the present invention, the water-soluble organic solvent is preferably 2-pyrrolidone, N-methylpyrrolidin-2-one, mono-, di- or triethylene glycol, dipropylene glycol, and more preferably 2-pyrrolidone, N- Methylpyrrolidin-2-one and diethylene glycol.
[0029]
Examples of the ink preparation agent include an antiseptic / antifungal agent, a pH adjuster, a chelating reagent, a rust inhibitor, a water-soluble ultraviolet absorber, a water-soluble polymer compound, a dye dissolving agent, a surfactant and the like. Examples of the antiseptic / antifungal agent include sodium acetate anhydride, sodium sorbate, sodium 2-pyridinethiol-1-oxide, sodium benzoate, sodium pentachlorophenol, 1,2-benzoisothiazolin-3-one and the like. As the pH adjuster, any substance can be used as long as it can control the pH of the ink within the range of 8.0 to 11.0 without adversely affecting the ink to be prepared. For example, alkanolamines such as diethanolamine and triethanolamine, hydroxides of alkali metals such as lithium hydroxide, sodium hydroxide and potassium hydroxide, ammonium hydroxide, and alkali metals such as lithium carbonate, sodium carbonate and potassium carbonate Carbonates and the like. Examples of the chelating reagent include sodium ethylenediaminetetraacetate, sodium nitrilotriacetate, sodium hydroxyethylethylenediaminetriacetate, sodium diethylenetriaminepentaacetate, and sodium uramildiacetate. Examples of the rust preventive include acidic sulfite, sodium thiosulfate, ammonium thioglycolate, diisopropylammonium nitrite, pentaerythritol tetranitrate, dicyclohexylammonium nitrite and the like. Examples of the water-soluble ultraviolet absorber include sulfonated benzophenone and sulfonated benzotriazole. Examples of the water-soluble polymer compound include polyvinyl alcohol, cellulose derivatives, polyamine, polyimine and the like. Examples of the dye dissolving agent include urea, ε-caprolactam, ethylene carbonate and the like. Examples of the surfactant include an anionic surfactant, an amphoteric surfactant, a cationic surfactant, and a nonionic surfactant. Examples of anionic surfactants include alkyl sulfocarboxylates, α-olefin sulfonates, polyoxyethylene alkyl ether acetates, N-acyl amino acids and salts thereof, N-acylmethyl taurine salts, alkyl sulfate polyoxyalkyl ethers Sulfate, alkyl sulfate polyoxyethylene alkyl ether phosphate, rosin acid soap, castor oil sulfate, lauryl alcohol sulfate, alkylphenol phosphate, alkyl phosphate, alkyl allyl sulfonate, diethyl sulfosuccinate And diethylhexylsulfosuccinate dioctylsulfosuccinate. Examples of the cationic surfactant include a 2-vinylpyridine derivative and a poly-4-vinylpyridine derivative. Examples of the amphoteric surfactant include betaine lauryldimethylaminoacetate, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, coconut oil fatty acid amide propyldimethylaminoacetate betaine, polyoctyl polyaminoethyl glycine, and other imidazoline derivatives. is there. Nonionic surfactants include polyoxyethylene nonyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene dodecyl phenyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene Ethers such as alkyl ethers and polyoxyallylalkyl alkyl ethers, polyoxyethylene oleic acid, polyoxyethylene oleate, polyoxyethylene distearate, sorbitan laurate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquiate Esters such as oleate, polyoxyethylene monooleate and polyoxyethylene stearate, 2,4,7 Acetylene glycols such as 9-tetramethyl-5-decyne-4,7-diol, 3,6-dimethyl-4-octyne-3,6-diol, 3,5-dimethyl-1-hexyn-3-ol (for example, And Surfynol 104, 104E, 104PG50, 82, 465, and Olfin STG manufactured by Nissin Chemical Co., Ltd.). These ink preparations are used alone or as a mixture.
[0030]
The aqueous magenta ink composition of the present invention can be produced by dissolving the monoazo compound represented by the formula (1) in water or the above-mentioned aqueous solvent (water containing a water-soluble organic solvent) together with the above-mentioned ink preparation agent and the like.
When this aqueous magenta ink composition is used as an ink for an ink jet printer, it is preferable to use a monoazo compound having a low content of inorganic substances such as chlorides and sulfates of metal cations. Is, for example, about 1% or less. In order to produce a monoazo compound having a small amount of inorganic substances, desalting may be carried out by an ordinary method such as a method using a reverse osmosis membrane.
In the production method of the present invention, the order of dissolution is not particularly limited. After previously dissolving in water or the above-mentioned aqueous solvent (water containing a water-soluble organic solvent), an ink preparation may be added and dissolved, or after dissolving the monoazo compound represented by the formula (1) in water, An aqueous solvent and an ink preparation may be added and dissolved. The order may be different from that described above, or an aqueous solvent and an ink preparation agent may be added to a reaction solution of the monoazo compound represented by the formula (1) or a solution that has been subjected to a desalination treatment using a reverse osmosis membrane. A composition may be manufactured. The water to be used is preferably a substance having few impurities such as ion-exchanged water or distilled water. Further, if necessary, fine filtration may be performed using a membrane filter or the like to remove impurities. When used as an ink for an inkjet printer, it is preferable to perform fine filtration. The pore size of the filter for microfiltration is 1 micron to 0.1 micron, preferably 0.8 micron to 0.2 micron.
[0031]
The recording liquid containing at least one compound represented by the formula (1) is suitable for use in printing, copying, marking, writing, drafting, stamping, or recording, particularly ink jet printing. In this case, high quality magenta prints having good resistance to water, sunlight, ozone and rubbing are obtained. By blending a dye such as yellow or cyan with the monoazo dye represented by the formula (1), the desired magenta color tone can be obtained.
[0032]
The colored body of the present invention is colored with the above-mentioned compound of the present invention. The material to be colored is not particularly limited, and examples thereof include, but are not limited to, paper, fiber and cloth (cellulose, nylon, wool, and the like), leather, and a base material for a color filter. Examples of the coloring method include a printing method such as a dip dyeing method, a printing method, a screen printing method, and a method using an ink jet printer, and a method using an ink jet printer is preferable.
[0033]
Examples of the recording material to which the inkjet recording method of the present invention can be applied include an information transmission sheet such as paper and a film, a fiber, and leather. The information transmission sheet is preferably a surface-treated sheet, specifically, a sheet provided with an ink receiving layer on these substrates. The ink receiving layer is, for example, by impregnating or coating the above-mentioned base material with a cationic polymer, and also, porous silica, alumina sol or inorganic fine particles capable of absorbing a dye in the ink such as special ceramics such as polyvinyl alcohol and polyvinyl pyrrolidone. It is provided by coating the substrate surface together with the hydrophilic polymer. A sheet provided with such an ink receiving layer is generally called a paper (film) or a glossy sheet (film) for exclusive use of ink jet, for example, Pictorico (manufactured by Asahi Glass Co., Ltd.), color BJ paper, color BJ photo film sheet (all It is commercially available as a color image jet paper (manufactured by Sharp Corporation), a glossy film for exclusive use of Super Fine (manufactured by Epson Corporation), Pictafine (manufactured by Hitachi Maxell Corporation), and the like. Of course, it can also be used for plain paper.
[0034]
In the inkjet recording method of the present invention, the aqueous magenta ink composition of the present invention can be used in combination with a yellow ink composition, a cyan ink composition, and, if necessary, a black ink composition.
The ink composition of each color is poured into each container, and this container is set (loaded) at a predetermined position of an ink jet printer and used like the container containing the aqueous magenta ink composition of the present invention. .
[0035]
In order to perform recording on a recording material by the inkjet recording method of the present invention, for example, a container containing the above ink composition is set at a predetermined position of an inkjet printer, and recording may be performed on the recording material by a normal method. . Examples of the ink jet printer include a piezo printer using mechanical vibration and a bubble jet (registered trademark) printer using bubbles generated by heating.
[0036]
The aqueous ink composition of the present invention has a vivid magenta color, and particularly has high light fastness and ozone fastness on inkjet glossy paper. It is also highly safe for humans. By using it with other yellow and cyan inks, it is possible to produce a color tone in a wide visible range, and when used with yellow, cyan and black, which have excellent light and ozone resistance, it has particularly excellent ozone resistance. In addition, it is possible to obtain a recorded matter excellent in light resistance and water resistance.
[0037]
The ink according to the invention does not settle or separate during storage. Also, when the ink according to the present invention is used in ink-jet printing, the ejector is not blocked. The physical properties of the inks according to the invention do not change under constant recirculation of the inks according to the invention for a relatively long period of time by means of a continuous ink jet printer or even intermittently by means of an on demand ink jet printer.
[0038]
【Example】
Hereinafter, the present invention will be described more specifically with reference to Examples. In the text, “parts” and “%” are based on weight unless otherwise specified.
[0039]
Example 1
According to a conventional method, 12.9 parts of cyanuric chloride and 13.0 parts of 2,4-diaminobenzenesulfonic acid are primarily condensed in an aqueous medium at pH 3-5 at a temperature of 0-5 ° C, and the resulting compound is subjected to a conventional method. Diazotize with 22 parts of 35% hydrochloric acid and 12.7 parts of 40% sodium nitrite, 29.0 parts of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid, pH 5-6, temperature 10-15 ° C. And coupled. Next, 12.0 parts of 3,5-dicarboxyaniline is subjected to secondary condensation at pH 5-6 at a temperature of 40-45 ° C for 4 hours, and further at pH 9.5-10.0 at a temperature of 90-95 ° C for 6 hours. The resulting product is subjected to salting out and filtration according to a conventional method to obtain a monoazo compound (λmax in water = 515 nm in water) represented by the following formula (9) (Compound Example No. 9) having an acid type structure. Obtained.
[0040]
Embedded image
Example 2
According to a conventional method, 12.9 parts of cyanuric chloride and 13.0 parts of 2,4-diaminobenzenesulfonic acid are primarily condensed in an aqueous medium at pH 3-5 at a temperature of 0-5 ° C, and the resulting compound is subjected to a conventional method. Diazotize with 22 parts of 35% hydrochloric acid and 12.7 parts of 40% sodium nitrite, 29.0 parts of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid, pH 5-6, temperature 10-15 ° C. And coupled. Next, 12.0 parts of 3,5-dicarboxyaniline is subjected to secondary condensation at pH 5-6 at a temperature of 40-45 ° C. for 4 hours, and 42.9 parts of 4-hydroxy-5-carboxyaniline is further subjected to pH 4-5 at a temperature of 80-80 ° C. A third condensation is carried out at 85 ° C. for 4 hours, and the obtained product is salted out and filtered according to a conventional method to obtain a monoazo compound represented by the following formula (10) (Compound Example No. 11) having an acid type structure (Compound Example No. 11): Λmax = 518 nm in water) was obtained.
[0042]
Embedded image
Example 3-12
In place of 3,5-dicarboxyaniline used in the second condensation in Example 2, the compound in the first column of Table 2 below was replaced with 4-hydroxy-5-carboxyaniline used in the third condensation. Each compound in the second column was synthesized in the same manner as in Example 2 to obtain a corresponding monoazo compound.
In Example 3, Compound Example No. 38, Example 4 shows compound example no. 12, in Example 5, Compound Example No. 13, in Example 6, Compound Example No. 52, and in Example 7, Compound Example No. 53, and in Example 8, Compound Example No. In Example 9, Compound Example No. 54 was used. 41, and in Example 10, Compound Example No. 36, and in Example 11, Compound Example No. 43, Example 12 shows compound example no. 58 were each obtained.
[0044]
Example 13
Example 1 was repeated using 1-benzenesulfonylamino-8-hydroxynaphthalene-3,6-disulfonic acid instead of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid used in Example 1. When synthesized in a similar manner, a monoazo compound having an acid structure and represented by the following formula (11) (Compound Example No. 28) was obtained.
[0046]
Embedded image
Example 14
Similar to Example 1 except that 1-benzoylamino-8-hydroxynaphthalene-4,6-disulfonic acid was used instead of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid used in Example 1. The monoazo compound represented by the following formula (12) (Compound Example No. 30) having an acid structure is obtained.
[0048]
Embedded image
Examples 15 and 16
(A) Preparation of ink
Liquids having the compositions shown in Table 5 were prepared using the compounds obtained in Examples 1 and 3 above, and filtered with a 0.45 μm membrane filter to obtain each aqueous ink composition for inkjet. Water used was ion-exchanged water. In addition, water and sodium hydroxide were added so that the pH of the ink composition was 8 to 10 and the total amount was 100 parts. A test using the compound obtained in Example 1 is referred to as Example 15, and a test using the compound obtained in Example 3 is referred to as Example 16.
[0050]
Table 5 (ink composition)
3.0 parts of the compound obtained in the above example
Water + 77.9 parts of sodium hydroxide
Glycerin 5.0 parts
Urea 5.0 parts
N-methyl-2-pyrrolidone 4.0 parts
3.0 parts of isopropyl alcohol
Butyl carbitol 2.0 parts
Surfynol 104PG50 (Nissin Chemical Co.) 0.1 part
100.0 copies in total
[0051]
(B) Inkjet printing
Using an inkjet printer (trade name: BJ-S630 manufactured by Canon Inc.), two types of plain paper (printer paper A4 TLB5A4S (manufactured by Canon Inc.)) and glossy paper having a dye receiving layer (PM photo paper KA420PSK manufactured by Epson) are used. Ink jet recording was performed.
[0052]
Hereinafter, as a comparative test, an ink was prepared and evaluated so as to have the same print density as the ink of Example 1.
Comparative Example 1
As a comparative object, C.I. which is widely used as a magenta dye for inkjet instead of the compound obtained in Example 3 is used. I. An ink was prepared with the same composition as in Example 1 except that 2.5 parts of Direct Red 227 (the following formula (13)) was used, inkjet recording was performed, and the recorded image was evaluated.
[0053]
Embedded image
Comparative Example 2
Patent Document 3, Compound No. 3, which is widely used as a magenta dye for inkjet instead of the compound obtained in Example 3 as a comparative object. An ink was prepared with the same composition as in Example 1 except that 2 parts of the compound described in (1) (the following formula (14)) was used, inkjet recording was performed, and the recorded image was evaluated.
[0055]
Embedded image
(C) Evaluation of recorded image
1. Hue evaluation
1-1. Hue evaluation on glossy paper
Hue and clarity of the recorded image: The color of the recording paper was measured using a colorimetric system (GRETAG SPM50: manufactured by GRETAG). * , A * , B * Values were calculated. Hue is compared with standard magenta color sample of JAPAN Color of JNC (Japan Printing Industry Machinery Association). * = ((A * ) 2 + (B * ) 2 ) 1/2 Was evaluated.
Table 6 shows the results of color samples of JNC JAPAN Color standard magenta and the hue of glossy paper of Examples 15 and 16.
[0057]
From Table 6, it can be seen that the monoazo compound of the present invention is close to the hue of JNC standard magenta and is an ideal hue.
[0059]
1-2. Hue evaluation on plain paper
Table 7 shows the results of the hues of the plain papers of Example 15, Comparative Example 1, and Comparative Example 2 in the same manner as described above.
[0060]
According to Table 7, the monoazo compound of the present invention has a hue recorded on plain paper having a C value higher than that of Comparative Examples 1 and 2. * It is understood that the value is high and the sharpness is very high.
[0062]
(D) Xenon light fastness test of recorded images
The test piece printed on the glossy paper was irradiated with an xenon weatherometer Ci4000 (manufactured by ATLAS) at an illuminance of 0.36 W / m 2 for 50 hours, and the color difference (ΔE) and residual density (%) before and after the test (before the test) Concentration / concentration after test × 100) was measured. The results are shown in Table 8.
(E) Ozone resistance test of recorded images
A test piece printed on glossy paper was introduced into an ozone weather meter with a humidifier, and an ozone weather meter (model OMS-H manufactured by Suga Test Instruments Co., Ltd.) maintained at a humidity of 60% was used. It was left at a concentration of 12 ppm for 2 hours, and the color difference (ΔE) and the residual concentration (%) before and after the test (concentration after test / concentration before test × 100) were measured. The results are shown in Table 8.
[0063]
(F) Moisture resistance test of recorded image
The test piece printed on the glossy paper was allowed to stand at 50 ° C. and 90% RH for 7 days using a thermo-hygrostat (manufactured by Applied Giken Sangyo Co., Ltd.), and bleeding of the dye before and after the test was visually determined.
○ Little bleeding is seen in the dye.
Δ: Dye bleeding is slightly observed.
X: Dye bleeding is considerably observed.
[0064]
Table 8 shows that Example 15 has stronger light resistance and ozone resistance than Comparative Example 1, and has stronger ozone resistance and moisture resistance than Comparative Example 2. It can be seen that the light resistance and the ozone resistance of Comparative Example 16 are stronger than Comparative Examples 1 and 2, and the moisture resistance is stronger than Comparative Example 2.
It can be seen that the magenta ink using the monoazo compound of the present invention is a very excellent magenta color ink having an overall strong hue, light fastness, fastness against ozone, and moisture fastness.
[0066]
Example 17
According to a conventional method, 18.8 parts of cyanuric chloride and 18.8 parts of 2,4-diaminobenzenesulfonic acid are primarily condensed in an aqueous medium at pH 3-6 at a temperature of 0-5 ° C., and the resulting compound is subjected to a conventional method. To diazotize with hydrochloric acid and sodium nitrite to couple with 13.6 parts of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid at pH 7-8 at a temperature of 5-10 ° C. Then, 18.1 parts of 5-aminoisophthalic acid is subjected to secondary condensation at pH 5-6 at a temperature of 40-50 ° C., and 26.7 parts of sodium 3-mercapto-1-propanesulfonate is added thereto to add a pH of 8-10 and a temperature of 85-85. Tertiary condensation was performed at 95 ° C. The resulting product was salted out and filtered according to a conventional method to obtain a monoazo compound (λmax in water = 517 nm) represented by the following formula (16) (Compound Example No. 61) having an acid structure. .
[0067]
Embedded image
Example 18
According to a conventional method, 18.8 parts of cyanuric chloride and 18.8 parts of 2,4-diaminobenzenesulfonic acid are primarily condensed in an aqueous medium at pH 3-6 at a temperature of 0-5 ° C., and the resulting compound is subjected to a conventional method. To diazotize with hydrochloric acid and sodium nitrite, and coupled with 43.6 parts of 1-benzoylamino-8-hydroxynaphthalene-3,6-disulfonic acid at pH 7-8 at a temperature of 5-10 ° C. Then, 18.1 parts of 5-aminoisophthalic acid was subjected to secondary condensation at pH 5-6 at a temperature of 40-50 ° C, and 18.7 parts of taurine was further added to perform tertiary condensation at a pH of 7-9 and a temperature of 85-95 ° C. . The obtained product was salted out and filtered according to a conventional method to obtain a monoazo compound (λmax in water = 520 nm in water) represented by the following formula (16) (Compound Example No. 63) having an acid structure.
Embedded image
Examples 19 and 20
(A) Preparation of ink
An ink was prepared with the same ink composition as in Table 5 in Example 15 except that 2.8 parts of the compound obtained in Example 17 was used, and ink-jet recording was performed in the same manner as in (B), and a recorded image was formed. Was evaluated. This is Example 19.
An ink was prepared with the same ink composition as in Table 5 in Example 15 except that 3.3 parts of the compound obtained in Example 18 was used, and ink-jet recording was performed in the same manner as in (B) above, and the recorded image was recorded. An evaluation was performed. This is Example 20.
[0070]
(C) Evaluation of recorded image; Hue evaluation 1-2. The hue and sharpness of the recorded image were measured in the same manner as in the evaluation of hue on plain paper. Table 9 shows the results.
[0071]
According to Table 9, the azo compound of the present invention has a hue recorded on plain paper having a C value higher than that of Comparative Examples 1 and 2. * It is understood that the value is high and the sharpness is very high.
[0073]
The ozone resistance test and the moisture resistance test of the recorded image were performed in the same manner as (E) the ozone resistance test of the recorded image and (F) the moisture resistance test of the recorded image. Table 10 shows the results.
[0074]
Table 10 shows that Examples 19 and 20 have stronger ozone resistance and moisture resistance than Comparative Example 2.
It can be seen that the magenta ink using the monoazo compound of the present invention is a very excellent magenta color ink having an overall strong hue, light fastness, fastness against ozone, and moisture fastness.
[0076]
【The invention's effect】
The compound of the present invention is characterized by having excellent water solubility and good filterability on a membrane filter in the process of producing an ink composition. Further, the ink composition of the present invention using this compound does not have crystal precipitation, physical property change, color change and the like after storage for a long period of time, and has good storage stability. A printed matter using the ink composition of the present invention as a magenta ink for inkjet recording has an ideal magenta hue without selecting a medium (paper, film, etc.). In addition, it is very excellent in light resistance and ozone resistance. Further, when the magenta ink composition of the present invention is used together with yellow, cyan, and black inks, ink jet recording excellent in light resistance, ozone resistance, and the like can be performed. Therefore, the compound of the present invention is extremely useful as a magenta ink for inkjet recording.
Claims (16)
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| JP2003187689A JP4497448B2 (en) | 2002-07-04 | 2003-06-30 | Water-soluble monoazo compound, aqueous magenta ink composition and colored body |
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| JP2003187689A JP4497448B2 (en) | 2002-07-04 | 2003-06-30 | Water-soluble monoazo compound, aqueous magenta ink composition and colored body |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009078252A1 (en) * | 2007-12-14 | 2009-06-25 | Nippon Kayaku Kabushiki Kaisha | Water-soluble anthrapyridone compound or salt thereof, ink composition, and colored material |
| US7614142B2 (en) | 2005-09-30 | 2009-11-10 | Fujitsu Limited | Method for fabricating an interposer |
| WO2012032985A1 (en) * | 2010-09-06 | 2012-03-15 | 日本化薬株式会社 | Ink set for use in inkjet recording, recording method, and colored substance |
| WO2012032986A1 (en) * | 2010-09-06 | 2012-03-15 | 日本化薬株式会社 | Ink set for inkjet recording, recording method, and colored body using same |
| CN106752060A (en) * | 2016-11-28 | 2017-05-31 | 黄山普米特新材料有限公司 | A kind of water base orchil and ink-jet imaging ink and preparation method thereof |
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| JPH09217018A (en) * | 1995-07-26 | 1997-08-19 | Ilford Ag | Dye for ink jet printing |
| US6068687A (en) * | 1997-11-20 | 2000-05-30 | Ilford Imaging Switzerland Gmbh | Azo dyes and their preparation and use |
| JP2001139836A (en) * | 1999-09-03 | 2001-05-22 | Nippon Kayaku Co Ltd | Anthrapyridone compound, aqueous magenta ink composition and ink jet recording method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH09217018A (en) * | 1995-07-26 | 1997-08-19 | Ilford Ag | Dye for ink jet printing |
| US6068687A (en) * | 1997-11-20 | 2000-05-30 | Ilford Imaging Switzerland Gmbh | Azo dyes and their preparation and use |
| JP2001139836A (en) * | 1999-09-03 | 2001-05-22 | Nippon Kayaku Co Ltd | Anthrapyridone compound, aqueous magenta ink composition and ink jet recording method |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7614142B2 (en) | 2005-09-30 | 2009-11-10 | Fujitsu Limited | Method for fabricating an interposer |
| WO2009078252A1 (en) * | 2007-12-14 | 2009-06-25 | Nippon Kayaku Kabushiki Kaisha | Water-soluble anthrapyridone compound or salt thereof, ink composition, and colored material |
| JP5306233B2 (en) * | 2007-12-14 | 2013-10-02 | 日本化薬株式会社 | Water-soluble anthrapyridone compound or a salt thereof, ink composition and colored body |
| WO2012032985A1 (en) * | 2010-09-06 | 2012-03-15 | 日本化薬株式会社 | Ink set for use in inkjet recording, recording method, and colored substance |
| WO2012032986A1 (en) * | 2010-09-06 | 2012-03-15 | 日本化薬株式会社 | Ink set for inkjet recording, recording method, and colored body using same |
| US8979988B2 (en) | 2010-09-06 | 2015-03-17 | Nippon Kayaku Kabushiki Kaisha | Ink set for inkjet recording, recording method, and colored body using same |
| AU2011300009B2 (en) * | 2010-09-06 | 2015-04-09 | Nippon Kayaku Kabushiki Kaisha | Ink set for inkjet recording, recording method, and colored body using same |
| EP2615143A4 (en) * | 2010-09-06 | 2015-05-06 | Nippon Kayaku Kk | Ink set for inkjet recording, recording method, and colored body using same |
| JP5885665B2 (en) * | 2010-09-06 | 2016-03-15 | 日本化薬株式会社 | Ink set for ink jet recording, recording method, and colored body using the same |
| CN106752060A (en) * | 2016-11-28 | 2017-05-31 | 黄山普米特新材料有限公司 | A kind of water base orchil and ink-jet imaging ink and preparation method thereof |
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| JP4497448B2 (en) | 2010-07-07 |
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