JP2716541B2 - 染料、染料組成物、染料の製造方法および染料組成物の製造方法 - Google Patents
染料、染料組成物、染料の製造方法および染料組成物の製造方法Info
- Publication number
- JP2716541B2 JP2716541B2 JP1216204A JP21620489A JP2716541B2 JP 2716541 B2 JP2716541 B2 JP 2716541B2 JP 1216204 A JP1216204 A JP 1216204A JP 21620489 A JP21620489 A JP 21620489A JP 2716541 B2 JP2716541 B2 JP 2716541B2
- Authority
- JP
- Japan
- Prior art keywords
- dye
- cooh
- acid
- salt
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 25
- -1 X is H Chemical group 0.000 claims description 22
- 239000011734 sodium Substances 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 229910052708 sodium Inorganic materials 0.000 claims description 17
- 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 claims description 16
- 150000003863 ammonium salts Chemical class 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 238000000502 dialysis Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002790 naphthalenes Chemical class 0.000 claims description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 239000000976 ink Substances 0.000 abstract description 60
- 238000007641 inkjet printing Methods 0.000 abstract description 10
- 229910006069 SO3H Inorganic materials 0.000 abstract 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 4
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 16
- 238000007639 printing Methods 0.000 description 14
- 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 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- OXSANYRLJHSQEP-UHFFFAOYSA-N 4-aminophthalic acid Chemical compound NC1=CC=C(C(O)=O)C(C(O)=O)=C1 OXSANYRLJHSQEP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- YDKMTSABXYVZHM-UHFFFAOYSA-N 5-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-6-sulfonaphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC(=CC=C11)S(O)(=O)=O)=CC=C1N=NC1=CC(C(O)=O)=CC(C(O)=O)=C1 YDKMTSABXYVZHM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 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
- 125000000129 anionic group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-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
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SXYRTDICSOVQNZ-UHFFFAOYSA-N 1-(2-methoxyethoxy)ethanol Chemical compound COCCOC(C)O SXYRTDICSOVQNZ-UHFFFAOYSA-N 0.000 description 1
- UQLFNNWJDJQVRF-UHFFFAOYSA-N 1-aminonaphthalene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C(C(O)=O)=CC2=C1 UQLFNNWJDJQVRF-UHFFFAOYSA-N 0.000 description 1
- VFFRLRQQWXGEBX-UHFFFAOYSA-N 1-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=CC2=C1 VFFRLRQQWXGEBX-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- UXLGYSHBBUFABE-UHFFFAOYSA-N 2-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]naphthalen-1-yl]diazenyl]terephthalic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)N=NC1=C(C=CC(=C1)C(=O)O)C(=O)O UXLGYSHBBUFABE-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- HHNWXQCVWVVVQZ-UHFFFAOYSA-N 2-amino-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(N)=C1 HHNWXQCVWVVVQZ-UHFFFAOYSA-N 0.000 description 1
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- NBUUUJWWOARGNW-UHFFFAOYSA-N 2-amino-5-methylbenzoic acid Chemical compound CC1=CC=C(N)C(C(O)=O)=C1 NBUUUJWWOARGNW-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- GPNNOCMCNFXRAO-UHFFFAOYSA-N 2-aminoterephthalic acid Chemical compound NC1=CC(C(O)=O)=CC=C1C(O)=O GPNNOCMCNFXRAO-UHFFFAOYSA-N 0.000 description 1
- ZBLNLEBUONEZMH-UHFFFAOYSA-N 3-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]naphthalen-1-yl]diazenyl]phthalic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)N=NC1=C(C(=CC=C1)C(=O)O)C(=O)O ZBLNLEBUONEZMH-UHFFFAOYSA-N 0.000 description 1
- SETVYNZSWPLKAO-UHFFFAOYSA-N 3-acetamido-5-aminobenzoic acid Chemical compound CC(=O)NC1=CC(N)=CC(C(O)=O)=C1 SETVYNZSWPLKAO-UHFFFAOYSA-N 0.000 description 1
- XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 description 1
- SMFDIRINQSURLB-UHFFFAOYSA-N 4-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-6-sulfonaphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)S(=O)(=O)O)N=NC1=C(C=C(C=C1)C(=O)O)C(=O)O SMFDIRINQSURLB-UHFFFAOYSA-N 0.000 description 1
- QFZMRWIHOBCFND-UHFFFAOYSA-N 4-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]naphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=C(C(O)=O)C=C1C(O)=O QFZMRWIHOBCFND-UHFFFAOYSA-N 0.000 description 1
- HDTOIOLTDIIMQI-UHFFFAOYSA-N 4-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]naphthalen-1-yl]diazenyl]phthalic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)N=NC1=CC(=C(C=C1)C(=O)O)C(=O)O HDTOIOLTDIIMQI-UHFFFAOYSA-N 0.000 description 1
- BDBLLWHZWCBDAR-UHFFFAOYSA-N 4-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC=C(C(O)=O)C=C1C(O)=O BDBLLWHZWCBDAR-UHFFFAOYSA-N 0.000 description 1
- ITYDCJUGUZXVHW-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(2-carboxy-4-methylphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=C(C=C1)C)C(=O)O ITYDCJUGUZXVHW-UHFFFAOYSA-N 0.000 description 1
- JKTCPFYXAFFVER-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(2-carboxy-4-sulfophenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=C(C=C1)S(=O)(=O)O)C(=O)O JKTCPFYXAFFVER-UHFFFAOYSA-N 0.000 description 1
- DOHZIFHDPMZJFJ-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(2-carboxy-5-chlorophenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=CC(=C1)Cl)C(=O)O DOHZIFHDPMZJFJ-UHFFFAOYSA-N 0.000 description 1
- ZUDKGFLUYNIAFX-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(2-carboxy-5-sulfophenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O ZUDKGFLUYNIAFX-UHFFFAOYSA-N 0.000 description 1
- NZDIIWZTTKPCHR-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(2-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=C(C=C11)C(O)=O)=CC=C1N=NC1=CC=CC=C1C(O)=O NZDIIWZTTKPCHR-UHFFFAOYSA-N 0.000 description 1
- AQNWRVDVEKJWLD-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(3-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=C(C=C11)C(O)=O)=CC=C1N=NC1=CC=CC(C(O)=O)=C1 AQNWRVDVEKJWLD-UHFFFAOYSA-N 0.000 description 1
- UOCFFNJSQOZVHD-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(4-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=C(C=C11)C(O)=O)=CC=C1N=NC1=CC=C(C(O)=O)C=C1 UOCFFNJSQOZVHD-UHFFFAOYSA-N 0.000 description 1
- KDVCXQAKSIFTAG-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(5-carboxy-2-methoxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical group OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=CC(=C1)C(=O)O)OC KDVCXQAKSIFTAG-UHFFFAOYSA-N 0.000 description 1
- MUAGQSOXEKUKPE-UHFFFAOYSA-N 5-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-8-[(5-carboxy-2-methylphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC(=CC=C12)C(=O)O)N=NC1=C(C=CC(=C1)C(=O)O)C MUAGQSOXEKUKPE-UHFFFAOYSA-N 0.000 description 1
- ZRUPOYCNMQLMLR-UHFFFAOYSA-N 5-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-7-carboxynaphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical group OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=C(C=C11)C(O)=O)=CC=C1N=NC1=CC(C(O)=O)=CC(C(O)=O)=C1 ZRUPOYCNMQLMLR-UHFFFAOYSA-N 0.000 description 1
- OHZNVQBTKCKTCF-UHFFFAOYSA-N 5-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-7-sulfonaphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=C(C=C11)S(O)(=O)=O)=CC=C1N=NC1=CC(C(O)=O)=CC(C(O)=O)=C1 OHZNVQBTKCKTCF-UHFFFAOYSA-N 0.000 description 1
- QCVIQBCXYSVKLR-UHFFFAOYSA-N 5-[[4-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]naphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC=1C2=CC(N)=CC=C2C=C(S(O)(=O)=O)C=1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC(C(O)=O)=CC(C(O)=O)=C1 QCVIQBCXYSVKLR-UHFFFAOYSA-N 0.000 description 1
- LNNIPFGPYVFLMG-UHFFFAOYSA-N 5-[[4-[[7-(2-carboxyethylamino)-1-hydroxy-3-sulfonaphthalen-2-yl]diazenyl]naphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)NCCC(=O)O)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)N=NC1=CC(=CC(=C1)C(=O)O)C(=O)O LNNIPFGPYVFLMG-UHFFFAOYSA-N 0.000 description 1
- WRZXVJSFVZDTFY-UHFFFAOYSA-N 5-[[4-[[7-(carboxymethylamino)-1-hydroxy-3-sulfonaphthalen-2-yl]diazenyl]naphthalen-1-yl]diazenyl]benzene-1,3-dicarboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)NCC(=O)O)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)N=NC1=CC(=CC(=C1)C(=O)O)C(=O)O WRZXVJSFVZDTFY-UHFFFAOYSA-N 0.000 description 1
- RDJCGBCRMNHAKG-UHFFFAOYSA-N 8-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-5-[(2-carboxy-5-sulfophenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)C(=O)O)N=NC1=C(C=CC(=C1)S(=O)(=O)O)C(=O)O RDJCGBCRMNHAKG-UHFFFAOYSA-N 0.000 description 1
- SHSRMCNTBQMFQF-UHFFFAOYSA-N 8-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-5-[(2-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)C(=O)O)N=NC1=C(C=CC=C1)C(=O)O SHSRMCNTBQMFQF-UHFFFAOYSA-N 0.000 description 1
- RYYNFCHXNIARQX-UHFFFAOYSA-N 8-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-5-[(3-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)C(=O)O)N=NC1=CC(=CC=C1)C(=O)O RYYNFCHXNIARQX-UHFFFAOYSA-N 0.000 description 1
- RZAGTTDUANSGGF-UHFFFAOYSA-N 8-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-5-[(4-carboxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)C(=O)O)N=NC1=CC=C(C=C1)C(=O)O RZAGTTDUANSGGF-UHFFFAOYSA-N 0.000 description 1
- HRQCMHDUKVXSLD-UHFFFAOYSA-N 8-[(7-amino-1-hydroxy-3-sulfonaphthalen-2-yl)diazenyl]-5-[(5-carboxy-2-methoxyphenyl)diazenyl]naphthalene-2-carboxylic acid Chemical compound OC1=C(C(=CC2=CC=C(C=C12)N)S(=O)(=O)O)N=NC1=CC=C(C2=CC=C(C=C12)C(=O)O)N=NC1=C(C=CC(=C1)C(=O)O)OC HRQCMHDUKVXSLD-UHFFFAOYSA-N 0.000 description 1
- PBWULNOSRHQTHZ-UHFFFAOYSA-N 8-aminonaphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(N)=CC=CC2=C1 PBWULNOSRHQTHZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OCAABGIZUTUMGP-UHFFFAOYSA-N COC(C(OCC)OCC)O Chemical compound COC(C(OCC)OCC)O OCAABGIZUTUMGP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/002—Influencing the physical properties by treatment with an amine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/01—Mixtures of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Coloring (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888820117A GB8820117D0 (en) | 1988-08-24 | 1988-08-24 | Anionic dye |
| GB8820117.3 | 1988-08-24 | ||
| GB898913460A GB8913460D0 (en) | 1989-06-12 | 1989-06-12 | Anionic dye |
| GB8913460.5 | 1989-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02140270A JPH02140270A (ja) | 1990-05-29 |
| JP2716541B2 true JP2716541B2 (ja) | 1998-02-18 |
Family
ID=26294317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1216204A Expired - Lifetime JP2716541B2 (ja) | 1988-08-24 | 1989-08-24 | 染料、染料組成物、染料の製造方法および染料組成物の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5053495A (https=) |
| EP (1) | EP0356080B1 (https=) |
| JP (1) | JP2716541B2 (https=) |
| KR (1) | KR0119910B1 (https=) |
| AT (1) | ATE106930T1 (https=) |
| AU (1) | AU614413B2 (https=) |
| DE (1) | DE68915896T2 (https=) |
| ES (1) | ES2055076T3 (https=) |
| GB (1) | GB8917764D0 (https=) |
| HK (1) | HK23297A (https=) |
| IN (1) | IN176153B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004113463A1 (en) | 2003-06-18 | 2004-12-29 | Fuji Photo Film Co., Ltd. | Ink and ink-jet recording ink |
| US7250079B2 (en) | 2003-01-08 | 2007-07-31 | Fujifilm Corporation | Coloring composition and inkjet recording method |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963189A (en) * | 1989-08-24 | 1990-10-16 | Hewlett-Packard Company | Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups |
| US5062893A (en) * | 1990-06-22 | 1991-11-05 | Hewlett-Packard Company | Ink formulations by mixing anionic waterfast dyes containing two or more carboxyl groups |
| DE4028630A1 (de) * | 1990-09-08 | 1992-03-12 | Basf Ag | Disazofarbstoffe deren kupplungskomponenten aus der reihe der hydroxysulfonylnaphthaline stammen |
| GB9100302D0 (en) * | 1991-01-08 | 1991-02-20 | Ici Plc | Compound |
| GB9101544D0 (en) * | 1991-01-24 | 1991-03-06 | Ici Plc | Compound |
| DE59209532D1 (de) * | 1991-07-19 | 1998-11-26 | Ciba Geigy Ag | Azofarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| US5250107A (en) * | 1991-07-31 | 1993-10-05 | Hewlett-Packard Company | Water-fast ink composition and method for making the same |
| US5223028A (en) * | 1991-08-19 | 1993-06-29 | Lexmark International, Inc. | Waterfast aqueous inks |
| US5198022A (en) * | 1991-10-25 | 1993-03-30 | Lexmark International, Inc. | Waterfast dye and aqueous ink |
| DE69302856T2 (de) * | 1992-04-10 | 1996-10-24 | Zeneca Ltd | Farbstoffzusammensetzungen und Tinten für das Tintenstrahldruckverfahren |
| JP3058230B2 (ja) * | 1993-01-25 | 2000-07-04 | キヤノン株式会社 | 記録紙及びこれを用いたインクジェット記録方法 |
| GB9303912D0 (en) * | 1993-02-26 | 1993-04-14 | Zeneca Ltd | Inks |
| EP0624632B1 (en) * | 1993-05-13 | 2003-08-06 | Mitsubishi Chemical Corporation | Recording liquid |
| WO1995000592A1 (en) * | 1993-06-18 | 1995-01-05 | Zeneca Limited | Disazo dyes |
| JP3072817B2 (ja) | 1993-11-04 | 2000-08-07 | キヤノン株式会社 | 記録紙、これを用いた画像形成方法および記録紙の製造方法 |
| DE4340354A1 (de) * | 1993-11-26 | 1995-06-01 | Bayer Ag | Neue Azofarbstoffe, deren Herstellung und Verwendung |
| GB9326232D0 (en) * | 1993-12-23 | 1994-02-23 | Zeneca Ltd | Chemical compounds |
| GB9326373D0 (en) * | 1993-12-23 | 1994-02-23 | Zeneca Ltd | Chemical compounds |
| JPH0881611A (ja) * | 1994-07-11 | 1996-03-26 | Canon Inc | 液体組成物、インクセット及びこれを用いた画像形成方法と装置 |
| DE4424484A1 (de) | 1994-07-12 | 1996-01-18 | Bayer Ag | Azofarbstoffe, deren Herstellung und Verwendung |
| AU3703595A (en) * | 1994-10-28 | 1996-05-23 | Zeneca Limited | Disaro colorant |
| GB9514386D0 (en) * | 1995-07-13 | 1995-09-13 | Zeneca Ltd | Stabilised dye composition |
| EP0753542B1 (de) * | 1995-07-14 | 2000-02-09 | Bayer Ag | Polyazofarbstoffe |
| EP0757087B1 (en) * | 1995-07-14 | 1999-09-15 | Mitsubishi Chemical Corporation | A recording liquid suitable for ink-jet recording |
| KR100414536B1 (ko) * | 1995-08-29 | 2004-03-20 | 주식회사 앤디앰 | 잉크제트용수용성흑색염료화합물 |
| EP0771860B1 (en) * | 1995-11-02 | 2002-01-09 | Seiko Epson Corporation | Ink composition excellent in reproduction of black color and ink jet recording method using the same |
| DE19636540A1 (de) * | 1996-09-09 | 1998-03-12 | Bayer Ag | Aminomethylnaphthalincarbonäsure-Farbstoffe |
| GB9621225D0 (en) * | 1996-10-11 | 1996-11-27 | Zeneca Ltd | Bisazo ink-jet dyes |
| GB9621224D0 (en) * | 1996-10-11 | 1996-11-27 | Zeneca Ltd | Bisazo ink-jet dyes |
| WO1998023690A1 (en) | 1996-11-27 | 1998-06-04 | Eastman Chemical Company | Method for preparing light-absorbing polymeric compositions |
| US5912280A (en) * | 1996-12-27 | 1999-06-15 | E. I. Du Pont De Nemours And Company | Ink jet inks containing emulsion-polymer additives to improve water-fastness |
| EP0859033B1 (en) | 1997-02-13 | 1999-06-23 | ILFORD Imaging Switzerland GmbH | Dyes for ink jet printing |
| US6251174B1 (en) * | 1997-04-01 | 2001-06-26 | Avecia Limited | Ink composition containing at least two azo dyes |
| GB9706580D0 (en) * | 1997-04-01 | 1997-05-21 | Zeneca Ltd | Ink additives |
| KR100420028B1 (ko) * | 1997-04-03 | 2005-07-07 | 제일모직주식회사 | 잉크젯 잉크용 흑색 염료 |
| DE69825937T2 (de) | 1997-05-22 | 2005-01-27 | Canon K.K. | Tintensortiment, Aufzeichnungsverfahren und Aufzeichnungsgerät unter Verwendung desselben |
| US6342095B1 (en) | 1997-05-22 | 2002-01-29 | Canon Kabushiki Kaisha | Ink set, and recording method and recording instrument using the same |
| EP0924263B1 (de) * | 1997-10-03 | 1999-07-28 | ILFORD Imaging Switzerland GmbH | Disazofarbstoffe, deren Herstellung und Verwendung |
| GB9812119D0 (en) * | 1998-06-05 | 1998-08-05 | Zeneca Ltd | Composition |
| US6221141B1 (en) | 1998-06-23 | 2001-04-24 | Canon Kabushiki Kaisha | Ink, ink-jet recording process, recording unit, ink cartridge and ink-jet recording apparatus |
| US6375317B1 (en) | 1998-10-27 | 2002-04-23 | Canon Kabushiki Kaisha | Ink, ink-jet recording process, recording unit, ink cartridge and ink-jet recording apparatus |
| US6277184B1 (en) | 1998-11-20 | 2001-08-21 | Seiko Epson Corporation | Black ink composition for ink jet recording |
| US6306994B1 (en) | 1999-05-14 | 2001-10-23 | E. I. Du Pont De Nemours And Company | Inks with enhanced substrate binding characteristics |
| KR20010087028A (ko) * | 2000-03-06 | 2001-09-15 | 함장환 | 잔디깎는 기계 |
| DE10015004A1 (de) | 2000-03-25 | 2001-09-27 | Clariant Gmbh | Schwarze Tris-Azo-Metall-Komplex-Farbstoffe |
| DE10125274A1 (de) * | 2001-05-23 | 2002-11-28 | Clariant Gmbh | Farbmittelkombination |
| JP4377254B2 (ja) | 2003-03-27 | 2009-12-02 | 富士フイルム株式会社 | インクセット |
| US7153350B2 (en) | 2003-12-10 | 2006-12-26 | Pitney Bowes Inc. | Water soluble colorants for ink jet printing |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1054816B (de) * | 1957-09-28 | 1959-04-09 | Bayer Ag | Verfahren zum Faerben von Lebensmitteln |
| US3963418A (en) * | 1974-08-01 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Yellow disazo acid dye solution |
| CH601437A5 (https=) * | 1975-04-24 | 1978-07-14 | Sandoz Ag | |
| DE3122636A1 (de) * | 1981-06-06 | 1982-12-23 | Basf Ag, 6700 Ludwigshafen | Sulfonsaeuregruppenhaltige disazofarbstoffe |
| US4557761A (en) * | 1982-12-01 | 1985-12-10 | Canon Kabushiki Kaisha | Recording liquid |
| JPS6081249A (ja) * | 1983-10-08 | 1985-05-09 | Mitsubishi Chem Ind Ltd | ジスアゾ系化合物 |
| US4626284A (en) * | 1983-10-08 | 1986-12-02 | Mitsubishi Chemical Industries Ltd. | Recording liquid |
| JPS60108470A (ja) * | 1983-11-17 | 1985-06-13 | Mitsubishi Chem Ind Ltd | ナフタレンジスアゾ系化合物 |
| GB8421551D0 (en) * | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| DE3619572A1 (de) * | 1986-06-11 | 1987-12-17 | Bayer Ag | Aufzeichnungsfluessigkeit fuer tintenstrahl-aufzeichnungssysteme |
| US4963189A (en) * | 1989-08-24 | 1990-10-16 | Hewlett-Packard Company | Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups |
-
1989
- 1989-08-03 GB GB898917764A patent/GB8917764D0/en active Pending
- 1989-08-08 IN IN707DE1989 patent/IN176153B/en unknown
- 1989-08-10 AT AT89308157T patent/ATE106930T1/de not_active IP Right Cessation
- 1989-08-10 EP EP89308157A patent/EP0356080B1/en not_active Expired - Lifetime
- 1989-08-10 ES ES89308157T patent/ES2055076T3/es not_active Expired - Lifetime
- 1989-08-10 DE DE68915896T patent/DE68915896T2/de not_active Expired - Lifetime
- 1989-08-24 JP JP1216204A patent/JP2716541B2/ja not_active Expired - Lifetime
- 1989-08-24 KR KR1019890012093A patent/KR0119910B1/ko not_active Expired - Fee Related
- 1989-08-24 AU AU40205/89A patent/AU614413B2/en not_active Ceased
- 1989-08-24 US US07/398,369 patent/US5053495A/en not_active Expired - Lifetime
-
1997
- 1997-02-27 HK HK23297A patent/HK23297A/en not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7250079B2 (en) | 2003-01-08 | 2007-07-31 | Fujifilm Corporation | Coloring composition and inkjet recording method |
| WO2004113463A1 (en) | 2003-06-18 | 2004-12-29 | Fuji Photo Film Co., Ltd. | Ink and ink-jet recording ink |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0356080A3 (en) | 1991-09-18 |
| ES2055076T3 (es) | 1994-08-16 |
| EP0356080B1 (en) | 1994-06-08 |
| US5053495A (en) | 1991-10-01 |
| IN176153B (https=) | 1996-02-10 |
| EP0356080A2 (en) | 1990-02-28 |
| GB8917764D0 (en) | 1989-09-20 |
| HK23297A (en) | 1997-02-27 |
| KR0119910B1 (ko) | 1997-10-22 |
| AU4020589A (en) | 1990-03-01 |
| DE68915896T2 (de) | 1994-09-22 |
| AU614413B2 (en) | 1991-08-29 |
| JPH02140270A (ja) | 1990-05-29 |
| DE68915896D1 (de) | 1994-07-14 |
| ATE106930T1 (de) | 1994-06-15 |
| KR900003311A (ko) | 1990-03-26 |
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