TW201219500A - Water-soluble azo compound or salt thereof, ink composition and colored body - Google Patents

Water-soluble azo compound or salt thereof, ink composition and colored body Download PDF

Info

Publication number: TW201219500A
Authority: TW; Taiwan
Prior art keywords: water; compound; formula; salt; ink
Prior art date: 2010-10-22

Application number

TW100138122A

Other languages

English (en)

Chinese (zh)

Inventor

Ryoutarou Morita

Noriko Kajiura

Original Assignee

Nippon Kayaku Kk

Priority date (The priority date 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 date listed.)

2010-10-22

Filing date

2011-10-20

Publication date

2012-05-16

2011-10-20 Application filed by Nippon Kayaku Kk filed Critical Nippon Kayaku Kk

2012-05-16 Publication of TW201219500A publication Critical patent/TW201219500A/zh

Links

-1 azo compound Chemical class 0.000 title claims abstract description 83
239000000203 mixture Substances 0.000 title claims abstract description 78
150000003839 salts Chemical class 0.000 title claims abstract description 41
150000001875 compounds Chemical class 0.000 claims abstract description 87
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 57
125000003277 amino group Chemical group 0.000 claims abstract description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 46
239000003960 organic solvent Substances 0.000 claims description 26
239000000463 material Substances 0.000 claims description 24
239000007787 solid Substances 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
238000004040 coloring Methods 0.000 claims description 11
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 6
235000011187 glycerol Nutrition 0.000 claims description 6
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
230000002421 anti-septic effect Effects 0.000 claims description 3
230000005540 biological transmission Effects 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910017053 inorganic salt Inorganic materials 0.000 claims description 3
125000001741 organic sulfur group Chemical group 0.000 claims description 3
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 claims description 2
JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 2
239000003429 antifungal agent Substances 0.000 claims description 2
229940121375 antifungal agent Drugs 0.000 claims description 2
239000004599 antimicrobial Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
150000004662 dithiols Chemical class 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims 2
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 1
NZEDMAWEJPYWCD-UHFFFAOYSA-N 3-prop-2-enylsulfonylprop-1-ene Chemical compound C=CCS(=O)(=O)CC=C NZEDMAWEJPYWCD-UHFFFAOYSA-N 0.000 claims 1
YECGTQXQSSDBQY-UHFFFAOYSA-N 4-methylpentane-1,2,3-triol Chemical compound CC(C)C(O)C(O)CO YECGTQXQSSDBQY-UHFFFAOYSA-N 0.000 claims 1
WHFMPDGXZXBKOR-UHFFFAOYSA-N C(C)(=O)OCC1=CC=CC=C1.BrCC(=O)O Chemical compound C(C)(=O)OCC1=CC=CC=C1.BrCC(=O)O WHFMPDGXZXBKOR-UHFFFAOYSA-N 0.000 claims 1
XDILZEPJCPEDLT-UHFFFAOYSA-N [Na].[O-][N+]1=CC=CC=C1S Chemical compound [Na].[O-][N+]1=CC=CC=C1S XDILZEPJCPEDLT-UHFFFAOYSA-N 0.000 claims 1
235000019441 ethanol Nutrition 0.000 claims 1
125000004995 haloalkylthio group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
WTJKUFMLQFLJOT-UHFFFAOYSA-N heptadecan-9-one Chemical compound CCCCCCCCC(=O)CCCCCCCC WTJKUFMLQFLJOT-UHFFFAOYSA-N 0.000 claims 1
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 1
229910017464 nitrogen compound Inorganic materials 0.000 claims 1
150000002830 nitrogen compounds Chemical class 0.000 claims 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 abstract description 22
238000001454 recorded image Methods 0.000 abstract description 11
239000001052 yellow pigment Substances 0.000 abstract description 11
238000004321 preservation Methods 0.000 abstract description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract description 3
239000000976 ink Substances 0.000 description 169
238000012360 testing method Methods 0.000 description 35
230000000052 comparative effect Effects 0.000 description 26
239000000049 pigment Substances 0.000 description 20
239000002253 acid Substances 0.000 description 19
239000007789 gas Substances 0.000 description 16
238000007639 printing Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
159000000000 sodium salts Chemical class 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
239000000975 dye Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000047 product Substances 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
239000003086 colorant Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000012546 transfer Methods 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
239000004471 Glycine Substances 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
239000000654 additive Substances 0.000 description 6
150000003863 ammonium salts Chemical class 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
239000002585 base Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000012535 impurity Substances 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
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 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
238000005562 fading Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
238000005259 measurement Methods 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000000052 vinegar Substances 0.000 description 5
235000021419 vinegar Nutrition 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000012528 membrane Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000000758 substrate Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000012295 chemical reaction liquid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
229910003002 lithium salt Inorganic materials 0.000 description 3
159000000002 lithium salts Chemical class 0.000 description 3
230000007774 longterm Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
230000000704 physical effect Effects 0.000 description 3
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000003860 storage Methods 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 2
ZDIRCGKEOWZBIM-UHFFFAOYSA-N 4-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=CC=C1S(O)(=O)=O ZDIRCGKEOWZBIM-UHFFFAOYSA-N 0.000 description 2
JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
235000016068 Berberis vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000008051 alkyl sulfates Chemical class 0.000 description 2
229960004050 aminobenzoic acid Drugs 0.000 description 2
239000002280 amphoteric surfactant Substances 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
229940000635 beta-alanine Drugs 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000003093 cationic surfactant Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000001514 detection method Methods 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
239000004744 fabric Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
235000013922 glutamic acid Nutrition 0.000 description 2
239000004220 glutamic acid Substances 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000002609 medium Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002736 nonionic surfactant Substances 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
230000019612 pigmentation Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920005862 polyol Polymers 0.000 description 2
150000003077 polyols Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical class 0.000 description 2
229940079827 sodium hydrogen sulfite Drugs 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000003458 sulfonic acid derivatives Chemical class 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000004034 viscosity adjusting agent Substances 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
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GPTFURBXHJWNHR-UHFFFAOYSA-N protopine acetate Natural products C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000001223 reverse osmosis Methods 0.000 description 1
150000003304 ruthenium compounds Chemical class 0.000 description 1
238000005185 salting out Methods 0.000 description 1
238000007650 screen-printing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
LROWVYNUWKVTCU-STWYSWDKSA-M sodium sorbate Chemical compound [Na+].C\C=C\C=C\C([O-])=O LROWVYNUWKVTCU-STWYSWDKSA-M 0.000 description 1
235000019250 sodium sorbate Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
210000003802 sputum Anatomy 0.000 description 1
208000024794 sputum Diseases 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical class OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
229940104261 taurate Drugs 0.000 description 1
229960003080 taurine Drugs 0.000 description 1
150000003866 tertiary ammonium salts Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000035922 thirst Effects 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000004711 α-olefin Substances 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Ink Jet Recording Methods And Recording Media Thereof (AREA)
Ink Jet (AREA)

TW100138122A 2010-10-22 2011-10-20 Water-soluble azo compound or salt thereof, ink composition and colored body TW201219500A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2010237380		2010-10-22

Publications (1)

Publication Number	Publication Date
TW201219500A true TW201219500A (en)	2012-05-16

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TW100138122A TW201219500A (en)	2010-10-22	2011-10-20	Water-soluble azo compound or salt thereof, ink composition and colored body

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JP (1)	JPWO2012053512A1 (ja)
TW (1)	TW201219500A (ja)
WO (1)	WO2012053512A1 (ja)

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JP7005271B2 (ja) *	2016-10-31	2022-02-10	日本化薬株式会社	アゾ化合物又はその塩、及びインク

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DE602005024458D1 (de) *	2005-10-25	2010-12-09	Nippon Kayaku Kk	Wasserlösliche azoverbindung, tintenzusammensetzung und gefärbtes material
US7951234B2 (en) *	2007-11-20	2011-05-31	Nippon Kayaku Kabushiki Kaisha	Water-soluble azo compound or salt thereof, ink composition and colored product
US8425676B2 (en) *	2009-04-28	2013-04-23	Nippon Kayaku Kabushiki Kaisha	Water-soluble AZO compound or salt thereof, ink composition, and colored article
US20120092400A1 (en) *	2009-06-17	2012-04-19	Nippon Kayaku Kabushiki Kaisha	Water-soluble azo compound or salt thereof, ink composition, and colored article
JP2011105798A (ja) *	2009-11-13	2011-06-02	Nippon Kayaku Co Ltd	水溶性アゾ化合物又はその塩、インク組成物及び着色体
WO2011086966A1 (ja) *	2010-01-15	2011-07-21	日本化薬株式会社	水溶性アゾ化合物又はその塩、インク組成物及び着色体

2011
- 2011-10-18 WO PCT/JP2011/073938 patent/WO2012053512A1/ja not_active Ceased
- 2011-10-18 JP JP2012539733A patent/JPWO2012053512A1/ja active Pending
- 2011-10-20 TW TW100138122A patent/TW201219500A/zh unknown

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WO2012053512A1 (ja)	2012-04-26
JPWO2012053512A1 (ja)	2014-02-24

Publication	Publication Date	Title
TWI488921B (zh)	2015-06-21	A water-soluble azo compound or a salt thereof, an ink composition and a coloring matter
WO2008053776A1 (en)	2008-05-08	Water-soluble azo compounds or salts thereof, ink compositions and colored products
TW200835751A (en)	2008-09-01	Anthrapyridone compounds, salt thereof, magenta ink composition and colored article
CN101297002B (zh)	2011-12-21	水溶性偶氮化合物、油墨组合物及着色体
TW201231566A (en)	2012-08-01	Water-soluble azo compound or salt thereof, ink composition, and colored object
TW200927735A (en)	2009-07-01	Water-soluble azo compound or salt thereof, ink composition and colored acticle
TW201113334A (en)	2011-04-16	Water-soluble azo compound or salt thereof, ink composition and colored body
TW200932838A (en)	2009-08-01	Water-soluble azo compound or salt thereof, ink composition and colored body
TW201502217A (zh)	2015-01-16	水溶性偶氮化合物或其鹽、墨水組成物及著色體
TW201219500A (en)	2012-05-16	Water-soluble azo compound or salt thereof, ink composition and colored body
JP2008088282A (ja)	2008-04-17	水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP2016098276A (ja)	2016-05-30	水溶性アゾ化合物又はその塩、インク組成物及び着色体
TW200948904A (en)	2009-12-01	Hydrosoluble anthrapyridone compound and salt thereof, ink composition and colored article
WO2011086966A1 (ja)	2011-07-21	水溶性アゾ化合物又はその塩、インク組成物及び着色体
TW201022368A (en)	2010-06-16	Water soluble azo compound or its salt, ink composition and coloured article
TW201235418A (en)	2012-09-01	Water-soluble azo compound, salt thereof, ink composition, and colored body
JP2017002106A (ja)	2017-01-05	水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP2017052861A (ja)	2017-03-16	水溶性アゾ化合物又はその塩、インク組成物及び着色体
TW201237113A (en)	2012-09-16	Water-soluble azo compound or salt thereof, ink composition and colored body
JP2017052862A (ja)	2017-03-16	水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP2014098083A (ja)	2014-05-29	水溶性アゾ化合物又はその塩、インク組成物及び着色体
TW201233732A (en)	2012-08-16	Water-soluble azo compound, salt thereof, ink composition, and colored body
TW201422727A (zh)	2014-06-16	水溶性偶氮化合物或其鹽、墨水組成物及著色體
JP2014098085A (ja)	2014-05-29	水溶性アゾ化合物又はその塩、インク組成物及び着色体
JP2016098275A (ja)	2016-05-30	水溶性アゾ化合物又はその塩、インク組成物及び着色体