WO2008001036A2 - Compound, composition and use - Google Patents
Compound, composition and use Download PDFInfo
- Publication number
- WO2008001036A2 WO2008001036A2 PCT/GB2007/002025 GB2007002025W WO2008001036A2 WO 2008001036 A2 WO2008001036 A2 WO 2008001036A2 GB 2007002025 W GB2007002025 W GB 2007002025W WO 2008001036 A2 WO2008001036 A2 WO 2008001036A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ink
- formula
- compound
- water
- sulpho
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 239000000203 mixture Substances 0.000 title claims description 46
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000000758 substrate Substances 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 16
- 238000007641 inkjet printing Methods 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- -1 sulpho group Chemical group 0.000 claims description 38
- 239000003086 colorant Substances 0.000 claims description 25
- 238000007639 printing Methods 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 239000000976 ink Substances 0.000 description 92
- 239000004753 textile Substances 0.000 description 18
- 239000000975 dye Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000049 pigment Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000003203 everyday effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229960003080 taurine Drugs 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- 229950006389 thiodiglycol Drugs 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- 229940043375 1,5-pentanediol Drugs 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229910018828 PO3H2 Inorganic materials 0.000 description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- ZBNARPCCDMHDDV-UHFFFAOYSA-N chembl1206040 Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=CC4=CC(=CC(N)=C4C=3O)S(O)(=O)=O)S(O)(=O)=O)C)=C(O)C2=C1N ZBNARPCCDMHDDV-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 150000003950 cyclic amides Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-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
- 239000012954 diazonium Substances 0.000 description 2
- XDBZPHDFHYZHNG-UHFFFAOYSA-L disodium 3-[(5-chloro-2-phenoxyphenyl)diazenyl]-4-hydroxy-5-[(4-methylphenyl)sulfonylamino]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=CC(C)=CC=C1S(=O)(=O)NC(C1=C2O)=CC(S([O-])(=O)=O)=CC1=CC(S([O-])(=O)=O)=C2N=NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 XDBZPHDFHYZHNG-UHFFFAOYSA-L 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical class C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Chemical class 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 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
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- ATVNKCYHJUDXDZ-UHFFFAOYSA-N 2,2-diethoxy-2-methoxyethanol Chemical compound CCOC(CO)(OC)OCC ATVNKCYHJUDXDZ-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-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
- VAJZCFLYJRMBFN-UHFFFAOYSA-N 4,4-dimethylmorpholin-4-ium Chemical compound C[N+]1(C)CCOCC1 VAJZCFLYJRMBFN-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- FIJIPZQZVLCOMB-UHFFFAOYSA-N 4-bromonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(Br)C2=C1 FIJIPZQZVLCOMB-UHFFFAOYSA-N 0.000 description 1
- UJEUBSWHCGDJQU-UHFFFAOYSA-N 4-chloro-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3Cl UJEUBSWHCGDJQU-UHFFFAOYSA-N 0.000 description 1
- SHCCGXNIGGRSMX-UHFFFAOYSA-N 4-chloronaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=C(Cl)C2=C1 SHCCGXNIGGRSMX-UHFFFAOYSA-N 0.000 description 1
- PSAGPCOTGOTBQB-UHFFFAOYSA-N 4-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=C(O)C2=C1 PSAGPCOTGOTBQB-UHFFFAOYSA-N 0.000 description 1
- YBUGOACXDPDUIR-UHFFFAOYSA-N 4-methoxy-2-nitrophenol Chemical compound COC1=CC=C(O)C([N+]([O-])=O)=C1 YBUGOACXDPDUIR-UHFFFAOYSA-N 0.000 description 1
- GBWNQBBVSVGAAL-UHFFFAOYSA-N 5-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1 GBWNQBBVSVGAAL-UHFFFAOYSA-N 0.000 description 1
- NQRLWRODNCDUHY-UHFFFAOYSA-N 6-n,6-n,2-trimethylacridine-3,6-diamine Chemical compound C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3C=C21 NQRLWRODNCDUHY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- NHJKVIPZERKDRA-UHFFFAOYSA-N CC(Nc(cc1S(O)(=O)=O)cc(-c2ccc3C(N4CCS(O)(=O)=O)=O)c1Oc(c(S(O)(=O)=O)c1)c2c3c1C4=O)=O Chemical compound CC(Nc(cc1S(O)(=O)=O)cc(-c2ccc3C(N4CCS(O)(=O)=O)=O)c1Oc(c(S(O)(=O)=O)c1)c2c3c1C4=O)=O NHJKVIPZERKDRA-UHFFFAOYSA-N 0.000 description 1
- XOWKBZSCXFRCNX-UHFFFAOYSA-N COc(cc1-c(c2c34)ccc3C(O3)=O)ccc1Sc2ccc4C3=O Chemical compound COc(cc1-c(c2c34)ccc3C(O3)=O)ccc1Sc2ccc4C3=O XOWKBZSCXFRCNX-UHFFFAOYSA-N 0.000 description 1
- AEJQATHDOACANJ-UHFFFAOYSA-N COc(cc1N)ccc1Oc(c1c2c(C(O3)=O)ccc1)ccc2C3=O Chemical compound COc(cc1N)ccc1Oc(c1c2c(C(O3)=O)ccc1)ccc2C3=O AEJQATHDOACANJ-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 239000004128 Copper(II) sulphate Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001085205 Prenanthella exigua Species 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229910007339 Zn(OAc)2 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- UZZFFIUHUDOYPS-UHFFFAOYSA-L disodium 4-amino-3,6-bis[[4-[(2,4-diaminophenyl)diazenyl]phenyl]diazenyl]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2ccc(cc2)N=Nc2c(N)c3c(O)c(N=Nc4ccc(cc4)N=Nc4ccc(N)cc4N)c(cc3cc2S([O-])(=O)=O)S([O-])(=O)=O)c(N)c1 UZZFFIUHUDOYPS-UHFFFAOYSA-L 0.000 description 1
- FTZLWXQKVFFWLY-UHFFFAOYSA-L disodium;2,5-dichloro-4-[3-methyl-5-oxo-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FTZLWXQKVFFWLY-UHFFFAOYSA-L 0.000 description 1
- 239000001041 dye based ink Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XQSBLCWFZRTIEO-UHFFFAOYSA-N hexadecan-1-amine;hydrobromide Chemical group [Br-].CCCCCCCCCCCCCCCC[NH3+] XQSBLCWFZRTIEO-UHFFFAOYSA-N 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical compound C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001042 pigment based ink Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 150000003385 sodium Chemical class 0.000 description 1
- VOLOMNBZWKDHEA-UHFFFAOYSA-M sodium 2-[4-[(1-anilino-3-hydroxy-1-oxobut-2-en-2-yl)diazenyl]phenyl]-6-methyl-1,3-benzothiazole-7-sulfonate Chemical compound CC(O)=C(N=NC1=CC=C(C=C1)C1=NC2=CC=C(C)C(=C2S1)S(=O)(=O)O[Na])C(=O)NC1=CC=CC=C1 VOLOMNBZWKDHEA-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SMBAGGHBUKLZPQ-UHFFFAOYSA-J tetrasodium 6-amino-4-hydroxy-3-[[7-sulfinato-4-[(4-sulfonatophenyl)diazenyl]naphthalen-1-yl]diazenyl]naphthalene-2,7-disulfonate Chemical compound C1=CC(=CC=C1N=NC2=C3C=CC(=CC3=C(C=C2)N=NC4=C(C5=CC(=C(C=C5C=C4S(=O)(=O)[O-])S(=O)(=O)[O-])N)O)S(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+] SMBAGGHBUKLZPQ-UHFFFAOYSA-J 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- GWAKFAUFNNPZFE-UHFFFAOYSA-K trisodium 2-[4-[(2-amino-4-oxidophenyl)diazenyl]anilino]-5-[(1-amino-8-oxido-7-phenyldiazenyl-3,6-disulfonaphthalen-2-yl)diazenyl]benzenesulfonate Chemical compound NC1=C(C(=CC2=CC(=C(C(=C12)O)N=NC1=CC=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])N=NC1=CC(=C(C=C1)NC1=CC=C(C=C1)N=NC1=C(C=C(C=C1)O)N)S(=O)(=O)[O-].[Na+].[Na+].[Na+] GWAKFAUFNNPZFE-UHFFFAOYSA-K 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/08—Naphthalimide dyes; Phthalimide 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
Definitions
- This invention relates to a process for the coloration of substrates by means of an ink jet printer and to inks suitable for use in the process.
- IJP Ink Jet printing
- Canadian patent application 2,531 ,625 describes textile ink jet printing processes using aqueous inks containing reactive dyes.
- the textile is treated with an ink-receptive pre-treatment composition, usually containing a strong alkali.
- the alkali removes the hydrogen atom from hydroxyl groups in sugars making up the textile material and renders them reactive towards dyes contained in the ink.
- the nucleophilic, deprotonated hydroxyl groups react with the reactive dye to form a covalent bond there between.
- the textile is heated to a temperature around 100 0 C using saturated steam in order to facilitate this covalent bond formation.
- the printed textile is washed to remove the pre-treatment composition and unfixed dye and then dried.
- inks In an increasingly cost conscious and competitive ink jet market, it is desirable for inks to be as cheap as possible. Desirably the inks produce brightly coloured prints with good fastness properties.
- a particular problem with many inks used in the home and office environment is that they fade quickly, particularly on contact with ozone. Fading is a particular problem with photographs because they are on display and spend long periods bathed in light and in contact with oxidising gases.
- the requirement for storage stable inks is more demanding in the home and office environment than in the field of textile printing. In the home environment printers are used less frequently than in say a textile printing factory and so inks need to be stable for longer periods of time.
- a process for printing an image on a substrate comprising applying to the substrate by means of an ink jet printer an ink comprising a water-soluble compound of Formula (1 ) which is free from fibre-reactive groups:
- each R 1 and R 2 independently is a substituent other than H; m and n each independently has a value of 0 to 4; (m+n) has a value of at least 1 ;
- X and Y each independently is O, S, SO, SO 2 or -NR 3 -; and R 3 is H or optionally substituted alkyl, aryl or heteroaryl.
- m and n each independently has a value of 1 to 4.
- m has a value of 1 or 2, especially 2.
- n has a value of 1 or 2, especially 1.
- the compound of Formula (1 ) has at least one sulpho group.
- the compound of Formula (1 ) has from 1 to 4 sulpho groups, preferably 1 to 3 sulpho groups, especially 2 to 3 sulpho groups.
- the compound of Formula (1 ) has at least one carboxy group, for example 1 or 2 carboxy groups.
- the compound of Formula (1 ) has at least one carboxy group and at least one sulpho group.
- At least one of the groups represented by R 1 and R 2 is a sulpho group.
- Preferred optionally substituted aryl groups are optionally substituted phenyl and optionally substituted naphthyl.
- Preferred optionally substituted heteroaryl groups are optionally substituted pyrrole, furan, thiophene, pyrazole, imidazole, triazole, thiazole, thiadiazole, pyridine, pyrimidine and pyrazine groups.
- at least one of the groups represented by R 1 and R 2 is a sulpho group;
- At least one of the groups represented by R 1 is Ci -4 -alkyI or Ci -4 - alkoxy.
- R 1 or R 2 is a substituent other than H it is preferably C 1-8 -alkyl, Ci -8 -alkoxy, NR 4 R 5 , NHCOR 4 , NHCONR 4 R 5 , -C(O)R 4 , -C(O)OR 4 , -C(O)NR 4 R 5 , PO 3 H 2 , -SR 4 , -SO 2 R 4 , -SO 2 NR 4 R 5 , -SOR 4 , sulpho, carboxy, CF 3 , CN, NO 2 , phenyl or halogen, wherein R 4 and R 5 are each independently H, Ci -4 -alkyl or Ci_ 4 -alkyl carrying a hydroxyl, carboxy or sulpho group, or R 4 and R 5 together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6-membered ring, or Ci -8 -alkyl, Ci-s-alkoxy, NR 4
- X is preferably O, -NR 3 - or S, more preferably O.
- R 1 is an electron donating group, more preferably a C 1-8 -alkyl, C 1-8 -alkoxy, NR 4 R 5 , NHCOR 4 , NHSO 2 R 4 ,
- Y is preferably O or -NR 3 -, more preferably -NR 3 -, wherein R 3 is as hereinbefore defined.
- Preferred optionally substituted alkyl groups are optionally substituted Ci -8 - alkyl, more preferably optionally substituted Ci -4 -alkyl, for example methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, optionally substituted by, for example, a hydroxy, halogen, carboxy or sulpho group.
- optionally substituted alkyl groups include trifluoromethyl, hydroxyethyl, sulphoethyl, sulphopropyl and carboxyethyl.
- R 1 and R 2 are each independently sulpho, carboxy, Ci -4 -aIkyl or C 1-4 -alkoxy.
- R 3 is preferably C 1-4 -alkyl carrying a sulpho group.
- Preferred optionally substituted 5- or 6-membered rings include, thiophene, pyrazole, imidazole, triazole, thiazole, thiadiazole and pyridine rings.
- Preferred optionally substituted aryl groups are optionally substituted phenyl and optionally substituted naphthyl.
- Preferred optional substituents for the abovementioned aryl group include Ci -8 -alkyl, Ci -8 -alkoxy, NR 4 R 5 , NHCOR 4 , NHCONR 4 R 5 , NHCOR 4 , -SR 4 , -C(O)R 4 , -C(O)OR 4 , -C(O)NR 4 R 5 , PO 3 H 2 ,carboxy, sulpho, -SO 2 R 4 , -SO 2 NR 4 R 5 , -SOR 4 , -SO 3 H, CF 3 , CN, NO 2 and halogen, wherein R 4 and R 5 are as hereinbefore defined.
- the compound of Formula (1 ) is as defined hereinbelow in relation to the second aspect of the present invention.
- the compounds of Formula (1 ) are yellow in colour.
- the compound of Formula (1 ) has a solubility in water at 2O 0 C of
- the printing process of the present invention has the advantage that it may use compounds which are simpler and therefore cheaper than those described in Canadian patent application 2,531 ,625.
- the inks used in the process have good storage stability. While not wishing to be limited to any particular theory, the absence of fibre-reactive groups may play a part in this stability.
- the chlorotriazine and beta sulphatoethyl sulphone reactive groups used in the dyes of Canadian patent application 2,531 ,625 are naturally labile and over time they may degrade, generating acids and other species which may affect the stability of the ink. In coarse textile printing this might be tolerable, but for printing photographs where high definition and true colours are very important it can be a problem.
- the resultant prints are generally very bright and show good resistance to fade on contact with ozone.
- the compounds of Formula (1) also have good operability in ink jet printers.
- Inks comprising compounds of Formula (1 ) demonstrate a low tendency to crust over or block nozzles when printed from an ink jet printer.
- Fiber-reactive groups are free from fibre-reactive groups because no such groups are required.
- the term fibre-reactive group is well known in the textile art and is described for example in EP 0356014 A1.
- Fibre-reactive groups are capable, under alkaline conditions, of reacting with the hydroxy! groups present in cellulosic fibres or with the amino groups present in natural fibres to form a covalent linkage between the fibre and the dye.
- the compounds of Formula (1) may be prepared by, for example, by condensing an amine of formula H 2 N-R 3 with a compound of Formula (2):
- R 1 , R 2 , m, n and X are as hereinbefore defined.
- temperatures of 11O 0 C to 16O 0 C are used for the condensation, with reaction times typically lasting from 1.5 to 5 hours.
- a zinc salt is present, e.g. zinc acetate.
- the dicarboxylic acid equivalent of the compound of Formula (2) may be used instead, i.e. where there anhydride ring has been opened to give two carboxylic acid groups.
- Suitable amines of formula H 2 N-R 3 include amino acids, for example taurine, 1-amino-3-sulphopropane, aspartic acid, glutamic acid, arginine, sulphanilic acid, metanilic acid and 1-amino-3-carboxy benzene.
- Water-soluble compounds of Formula (1 ) may also be prepared by sulphonation of the corresponding compound which lacks or has fewer sulpho groups. Oleum may be used as a sulphonating agent.
- Compounds of Formula (1 ) where Y is S may be prepared by ring opening the corresponding anhydride where Y is O and treating the resultant dicarboxylic acid with a sulphurising agent and then ring closing again.
- Compounds of Formula (1 ) where Y is SO or SO 2 may be prepared by oxidising the corresponding compound where Y is S, e.g. with a peroxide.
- the compounds of Formula (2) may be prepared by the general method of Peters and Behesti in the Journal of the Society of Dyers and Colorists, 1989, 105, 29.
- Compounds of Formula (1) may also be prepared by heating the diazonium salt of a compound of the Formula (3) in the presence of copper or a copper salt:
- Certain of the compounds of Formula (3) may be prepared by condensing the corresponding 4-bromo- or 4-chloronaphthalic acid compounds with optionally substituted 2-amino or 2-nitro phenols, thiophenols or anilines in organic solvents
- a suitable reducing agent e.g. hydrogen and a transition metal catalyst.
- the compounds of Formula (1) may be in the free acid or salt form.
- Preferred salts are, for example alkali metal salts, (especially lithium, sodium, potassium), ammonium, substituted ammonium and mixed salts thereof.
- Preferred metal salts are those with sodium, lithium, ammonium and substituted alkyl ammonium salts.
- Preferred ammonium and substituted alkyl ammonium salts have cations of the formula + NV 4 wherein each V independently is H or optionally substituted alkyl, or two groups represented by V are H or optionally substituted alkyl and the remaining two groups represented by V, together with the N atom to which they are attached, form a 5- or 6- membered ring
- each V independently is H or Ci -4 -aIkyl, more preferably H, CH3 or CH2CH 3 , especially H.
- Preferred cyclic cations comprise a morpholinyl, pyridinyl pr piperidinyl ring.
- Examples of cations include + NH 4 , morpholinium, piperidinium, pyridinium, (CHa) 3 N + H, (CHs) 2 N + H 2 , H 2 N + (CH 3 )(CH 2 CH 3 ), CH 3 N + H 3 , CH 3 CH 2 N + H 3 , H 2 N + (CH 2 CHa) 2 , CH 3 CH 2 CH 2 N + H 3 , (CHa) 2 CHN + H 3 , N + (CH 3 J 4 , N + (CH 2 CHs) 4 , N-methyl pyridinium, N,N-dimethyl piperidinium and N,N-dimethyl morpholinium. It is especially preferred that the compounds of Formula (1) are in the form of a sodium, lithium, potassium, ammonium, substituted ammonium salt or mixtures thereof.
- At least one of the groups represented by R 1 and R 2 is a sulpho group; and (ii) at least one of the groups represented by R 1 is Ci -4 -alkyI or C 1-4 - alkoxy.
- Y is preferably -NR 3 - wherein R 3 is C-i -4 -alkyl carrying a sulpho and/or carboxy group.
- m is 2, one of the groups represented by R 1 is C 1-4 -alkyl or C- M -alkoxy and the other is sulpho, n is 1 , R 2 is a sulpho group, X is O and Y is -NR 3 - wherein R 3 is C 1-4 -alkyl carrying a sulpho and/or carboxy group.
- the compounds of Formula (1 ) may be used as the sole colorant in inks because of their bright colour and good fastness properties. However, if desired, one may combine the present compounds with one or more further colorants if a different shade is required for a particular end use. When further colorants are included in the ink these are preferably selected from yellow, magenta, cyan and black colorants and combinations thereof, most preferably yellow or magenta colorants and combinations thereof.
- composition comprising; a) two or more water-soluble compounds of Formula (1 ) as defined in the first aspect of the present invention; or b) one or more water-soluble compound of Formula (1 ) as defined in the first aspect of the present invention and one or more colorants other than a water-soluble compound of Formula (1 ) as defined in the first aspect of the present invention.
- the water-soluble compound of Formula (1 ) present in the composition is as defined in the second aspect of the present invention.
- composition according to the third aspect of the present invention is mixed so as to provide a uniform colour.
- the colorant other than a water-soluble compound of Formula (1 ) (hereinafter referred to as "further colorant”) is optionally a pigment or a dye. Suitable further colorants are listed in the Colour Index International.
- the amounts of the compound and further colorant(s) present in the composition according to the third aspect of the present invention may be selected so as to adjust the shade or other properties as desired.
- Preferred further colorants include yellow, magenta, cyan and black pigments and yellow, magenta, cyan and black dyes.
- Suitable further colorants include, for example, yellow pigments, e.g. C.I. Pigment Yellow 55, 74, 93, 109, 110, 128, 138, 150, 151 , 154, 155, 180 and 185; yellow dyes, for example, C.I. Acid Yellow 17, 19, 23, 25, 32, 40, 42, 44, 49, 61 , 127, 151 , 199, 219; C.I.
- yellow pigments e.g. C.I. Pigment Yellow 55, 74, 93, 109, 110, 128, 138, 150, 151 , 154, 155, 180 and 185
- yellow dyes for example, C.I. Acid Yellow 17, 19, 23, 25, 32, 40, 42, 44, 49, 61 , 127, 151 , 199, 219; C.I.
- Pigment Violet 19 magenta dyes, for example PRO-JETTM Fast Magenta 2, PRO-JETTM Magenta BTX, 3BOA, 2BTX and 1T; C.I. Acid Red 52 and 249; C.I. Reactive Red 180, 31 and 23; and C.I. Direct Red 227; cyan pigments, for example C.I. Pigmento Blue 15, 15:1 , 15:2, 15:3, 15:4, 15:6, 16 and 60; cyan dyes, for example phthalocyanine colorants, especially C.I. Direct Blue 86, 199 and C.I. Acid Blue 9, 99; black pigments, for example C.I.
- magenta dyes for example PRO-JETTM Fast Magenta 2, PRO-JETTM Magenta BTX, 3BOA, 2BTX and 1T
- C.I. Acid Red 52 and 249 C.I. Reactive Red 180, 31 and 23
- C.I. Direct Red 227 cyan pigments, for example C.I. Pigmento Blue 15,
- Lexmark for example EP 0 539,178 A2, examples 1 , 2, 3, 4 and 5
- Orient Chemicals for example EP 0 347 803 A2, pages 5 to 6, azo dyes 3, 4, 5, 6, 7, 8, 12, 13, 14, 15 and 16
- Seiko Epson Corporation for example EP 0 347 803 A2 pages 5 to 6, azo dyes 3,
- the one or more further colorants for use in the 0 composition according to the third aspect of the invention comprise a water- soluble dye.
- composition according to the third aspect of the present invention preferably comprises:
- the composition may contain a single water-soluble compound of Formula (1 ) as defined in the first aspect of the present invention or a mixture thereof.
- the composition may contain in (b) a single water-soluble dye or a mixture of two or more water-soluble dyes other than a compound of Formula (1 ).5
- the compounds and compositions according to the second and third aspects of the present invention may be, and preferably are, purified to remove undesirable impurities before they are incorporated into inks for ink jet printing. Conventional techniques may be employed for purification, for example ultrafiltration, reverse osmosis and/or dialysis.
- an ink for ink jet printing comprising:
- a liquid medium comprising water and an organic solvent.
- the water-soluble compound of Formula (1 ) present in the ink is as defined in the second aspect of the present invention.
- a preferred ink according to the fourth aspect of the present invention comprises:
- the number of parts by weight of component (a) is preferably from 0.01 to 30, more preferably 0.1 to 20, especially from 0.5 to 15, and more especially from 1 to 5 parts.
- the number of parts by weight of component (b) is preferably from 99.99 to 70, more preferably from 99.9 to 80, especially from 99.5 to 85, and more especially from 99 to 95 parts.
- the number of parts (a) + (b) is 100 and all parts mentioned here are by weight.
- component (a) is completely dissolved in component (b).
- component (a) has a solubility in component (b) at 20 0 C of at least 10% by weight. This allows the preparation of liquid dye concentrates which may be used to prepare more dilute inks and reduces the chance of the compound(s) of component (a) of the ink precipitating if evaporation of the liquid medium occurs during storage.
- the weight ratio of water to organic solvent is preferably from 99:1 to 1 :99, more preferably from 99:1 to 50:50 and especially from 95:5 to 80:20. It is preferred that the organic solvent is a water-miscible organic solvent or a mixture of such solvents.
- Preferred water-miscible organic solvents include: Ci -6 -alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec- butanol, tert-butanol, n-pentanol, cyclopentanol and cyclohexanol; linear amides, preferably dimethylformamide or dimethylacetamide; ketones and ketone-alcohols, preferably acetone, methyl ether ketone, cyclohexanone and diacetone alcohol; water-miscible ethers, preferably tetrahydrofuran and dioxane; diols, preferably diols having from 2 to 12 carbon atoms, for example pentane-1 ,5-diol, ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol and thio
- Especially preferred water-miscible organic solvents are cyclic amides, especially 2-pyrrolidone, N-methyl-pyrrolidone and N-ethyl-pyrrolidone; diols, especially 1 ,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono- C- ⁇ - 4 -alkyl and C ⁇ -alkyl ethers of diols, more preferably mono- Ci_ 4 -alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxy- 2-ethoxy-2-ethoxyethanol.
- the water-immiscible organic solvent is preferably a polar solvent because this enhances solubility of the compound in the liquid medium.
- polar solvents include Ci -4 -alcohols.
- An especially preferred ink comprises:
- the ink may also contain additional components conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives, anti-cockle agents to reduce paper curling and surfactants which may be ionic or non-ionic.
- additional components conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives, anti-cockle agents to reduce paper curling and surfactants which may be ionic or non-ionic.
- the pH of the ink is preferably from 4 to 11 more preferably from 7 to 10.
- the viscosity of the ink at 25 0 C is preferably less than 5OmPa. s, more preferably less that 2OmPa. s and especially less than 5mPa.s.
- the ink according to the fourth aspect of the present invention preferably has a concentration of halide ions of less than 500 parts per million, more preferably less than 100 parts per million. It is especially preferred that the ink has less than 100, more preferably less than 50 parts per million of divalent and trivalent metals, wherein parts refer to parts by weight relative to the total weight of the ink. We have found that purifying the ink to reduce the concentration of these undesirable ions reduces nozzle blockage in ink jet printing heads, particularly in thermal ink jet printers.
- the ink of the present invention preferably forms the yellow ink of a yellow, magenta, cyan and black ink set.
- magenta ink may contain for example C.I. Direct Red 227, C.I. Acid Red 52, 249 or Pro-JetTM Fast Magenta 2
- the cyan ink may contain for example C.I. Direct Blue 86, 199, C.I. Acid Blue 9 or Pro- JetTM Fast Cyan 2
- the black ink may contain for example C.I. Direct Black 168, 199 or Pro-JetTM Fast Black 2. (Pro-Jet is a trade mark of Fujifilm Imaging Colorants Limited).
- each ink preferably contains a further colorant selected from the pigments indicated above as being suitable further colorants.
- the magenta inks may contain, for example, C.I Pigment 122, 202 and/or 209.
- the cyan ink may contain, for example, C.I. Pigment Blue 15:3, 15:4 and/or 16.
- the black may contain, for example, C.I. Pigment Black 7 and/or Cab-O- jetTM 300.
- the yellow ink may contain, for example, a compound of Formula (1 ) as defined in the first aspect of the present invention and one or more of the further yellow pigments indicated above as being suitable further colorants.
- the ink is as defined in the fourth aspect of the present invention.
- the ink jet printer preferably applies the ink to the substrate in the form of droplets which are ejected through a small orifice onto the substrate.
- Preferred ink jet printers are piezoelectric ink jet printers and thermal ink jet printers.
- thermal ink jet printers programmed pulses of heat are applied to the ink in a reservoir by means of a resistor adjacent to the orifice, thereby causing the ink to be ejected in the form of small droplets directed towards the substrate during relative movement between the substrate and the orifice.
- piezoelectric ink jet printers the oscillation of a small crystal causes ejection of the ink from the orifice.
- the substrate is preferably a plain or treated paper which may have an acid, alkaline or neutral character.
- treated papers include: Photo Paper Pro (PR101), Photo Paper Plus (PP101 ), Glossy Photo Paper (GP401 ), Semi Gloss Paper (SG101 ), Matte Photo Paper (MP101 ), (all available from Canon); Premium Glossy Photo Paper, Premium Semi gloss Photo Paper, ColorLifeTM, Photo Paper, Photo Quality Glossy Paper, Double-sided Matte Paper, Matte Paper Heavyweight, Photo Quality InkJet Paper, Bright White InkJet Paper, Premium Plain Paper, (all available from Seiko Epson Corp); HP All- in-One Printing Paper, HP Everyday InkJet Paper, HP Everyday Photo Paper Semi-glossy, HP Office Paper, HP Photo Paper, HP Premium High-Gloss Film, HP Premium Paper, HP Premium Photo Paper, HP Premium Plus Photo Paper, HP Printing Paper, HP Superior InkJet Paper, (all available from Hewlett Packard Inc.); Everyday Glossy Photo Paper, Premium
- an ink jet printer cartridge comprising a chamber and ink, wherein the ink is present in the chamber and the ink is as defined in the fourth aspect of the present invention.
- an ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined in the sixth aspect of the present invention.
- Example 1 The product of Example 1 (1.3g, 3.1 mmol) was added gradually to 20% oleum (10ml) at 0-5 0 C and the mixture was stirred at this temperature for 3 hours. After this time HPLC indicated the presence of a mixture of two new compounds. The reaction mixture was then stirred for a further 16 hours while gradually warming to room temperature. After this time HPLC showed complete conversion to the more polar of the 2 new compounds. The reaction mixture was then drowned out into ice and the product isolated by salting (10% NaCI). The resultant yellow solid was redissolved in water at pH7 and dialysed to low conductivity to provide the title product (1.3g) having absorption maxima at 425 and 445nm.
- Example 2 The method of Example 2 was repeated except that in place of the product of Example 1 there was used the product of Example 3. Compound (4) was found to have adsorption maxima at 440 and 465nm.
- Example 1 The method of Example 1 may be repeated except that in place of Intermediate (1) there is used Intermediate 2 (shown above) and in place of taurine there is used 3,5-disulpho aniline.
- Example 2 may be repeated except that in place of the product from Example 1 there is used a compound arising from performing the method of Example 1 using Intermediate (5) in place of Intermediate (1 ):
- Example 1 may be repeated except that in place of Intermediate (1) there is used Intermediate (7):
- Example 2 may be repeated except that in place of the product from Example 1 there is used the product from Example 8.
- the inks described in Tables I and Il may be prepared wherein the compound referred to in the first column is the product from the above Example of the same number. Numbers quoted in the second column onwards refer to the number of parts of the relevant ingredient and all parts are by weight.
- the inks may be applied to paper by thermal or piezo ink jet printing. The following abbreviations are used in Table I and II:
- NMP N-methyl pyrollidone
- MIBK methylisobutyl ketone
- TBT tertiary butanol
- Inks may be prepared having the formulations described in US Patent Application Publication No. 2005/0076806 except that a compound of Formula (1 ) as defined in the first aspect of the present invention is used in place of the colorant described therein.
- Preferred inks of this type are described in Table 1 at pages 9 and 10 of US 2005/0076806.
- Especially preferred inks of this type are described below in Table III below and they may be prepared by mixing the components indicated therein.
- the inks may be applied to paper by thermal or piezo ink jet printing.
- Surfynol 465 RTM is an acetylenic glycol-based surfactant available from Air Products.
- 2P is 2-pyrollidone.
- Example 12 Inks may be prepared having the formulations described above in Table III except that diethylene glycol mono n-butyl ether is used in place of triethylene glycol mono n-butyl ether. Still further inks may be prepared having the formulations described above in Table III except that N-methyl pyrollidone may be used in place of 2-pyrollidone.
- Example 13 Inks may be prepared having the formulations described above in Table III except that diethylene glycol mono n-butyl ether is used in place of triethylene glycol mono n-butyl ether. Still further inks may be prepared having the formulations described above in Table III except that N-methyl pyrollidone may be used in place of 2-pyrollidone.
- Example 13
- Inks may be prepared as described in Japanese Patent Application No. 2005-047987 except that a compound of Formula (1 ) as defined in the first aspect of the present invention is used in place of the colorant used therein.
- Preferred inks of this type are described in claim 3 and Table 1 (at [0054]) of JP2005- 047987.
- the inks contain 1 ,2-hexane diol.
- the black compositions A to D described in Table IV below may be prepared by mixing together the components in the amounts indicated. These black compositions may be used to prepare black ink jet printing inks, for example having an analogous formulation to the inks described in Table III above except that each of the black compositions described in Table IV is used instead of Compound 2 alone.
- the yellow compositions E to I described in Table V below may be prepared by mixing together the components indicated. These yellow compositions may be used to prepare ink jet printing inks, for example having an analogous formulation to the inks described in Table III above except that each of the yellow compositions described in Table V is used instead of Compound 2 alone. Table V
- Ink sets may be prepared wherein each ink has the formulation described for Ink A in Table III above, except that in the magenta, cyan and black inks Compound 2 was replaced by the colorant indicated in Table Vl below:
- Cab-O-jet is a trade mark of Cabot corporation.
- Pro-Jet is a trade mark of Fujifilm Imaging Colorants Limited.
- the ink sets described in Table Vl may be incorporated into a thermal ink jet printer and printed onto paper.
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- 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)
Abstract
Description
Claims
Priority Applications (1)
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GB0819432A GB2450661B (en) | 2006-06-28 | 2007-06-04 | Inkjet ink |
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GBGB0612784.9A GB0612784D0 (en) | 2006-06-28 | 2006-06-28 | Compound, composition and use |
GB0612784.9 | 2006-06-28 |
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WO2008001036A3 WO2008001036A3 (en) | 2008-06-19 |
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PCT/GB2007/002025 WO2008001036A2 (en) | 2006-06-28 | 2007-06-04 | Compound, composition and use |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013075980A1 (en) * | 2011-11-23 | 2013-05-30 | Sicpa Holding Sa | Polycyclic aromatic compounds containing an s atom or s(=0)2 group and their use as dyes |
WO2014105493A1 (en) * | 2012-12-28 | 2014-07-03 | Ecolab Usa Inc. | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
US8859688B2 (en) | 2011-05-25 | 2014-10-14 | Sicpa Holding Sa | Polymer-bonded quaterrylene and/or terrylene dyes and compositions containing same |
US9029442B2 (en) | 2010-05-25 | 2015-05-12 | Sicpa Holding Sa | Polymer-bonded perylene dyes and compositions containing same |
CN105143153A (en) * | 2013-03-18 | 2015-12-09 | 巴斯夫欧洲公司 | Perylenemonoimide and naphthalenemonoimide derivatives and their use in dye-sensitized solar cells |
US9249320B2 (en) | 2011-11-10 | 2016-02-02 | Sicpa Holding Sa | Polymer-bonded polycyclic aromatic hydrocarbons having nitrogen containing substituents |
WO2022059311A1 (en) * | 2020-09-15 | 2022-03-24 | コニカミノルタ株式会社 | Benzothioxanthene compound, resin particles, and fluorescent immunostaining reagent |
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US3888863A (en) * | 1970-04-14 | 1975-06-10 | Hoechst Ag | Benzoxanthene and benzothioxanthene dyestuffs and process for their manufacture |
US4242139A (en) * | 1978-02-03 | 1980-12-30 | Hoechst Aktiengesellschaft | Water soluble benzoxanthene dyestuffs for fluorescent inks |
US20060107869A1 (en) * | 2003-07-10 | 2006-05-25 | Dystar Textilf Deutschland Kg | Inks for digital textile printing with reactive yellow fluorescent dyes |
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DE2008491C3 (en) * | 1970-02-24 | 1975-01-23 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Benzoxanthene dyes and process for their preparation |
DE2017765C3 (en) * | 1970-04-14 | 1979-08-16 | Hoechst Ag, 6000 Frankfurt | Daytime luminescent pigments, their use and process for their production |
DE2238457A1 (en) * | 1972-08-04 | 1974-02-14 | Hoechst Ag | PROCESS FOR COLORING SYNTHETIC FIBER MATERIALS FROM ORGANIC SOLVENTS |
DE2815031A1 (en) * | 1978-04-07 | 1979-10-18 | Hoechst Ag | USE OF COLORS FOR FLUORESCENCE-ACTIVATED BRIGHTNESS GAIN |
JP3779625B2 (en) * | 2002-01-29 | 2006-05-31 | 日本化薬株式会社 | Light emitting element |
JP4338981B2 (en) * | 2003-01-21 | 2009-10-07 | 日本化薬株式会社 | Dye-sensitized photoelectric conversion element |
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2006
- 2006-06-28 GB GBGB0612784.9A patent/GB0612784D0/en not_active Ceased
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2007
- 2007-06-04 GB GB0819432A patent/GB2450661B/en not_active Expired - Fee Related
- 2007-06-04 WO PCT/GB2007/002025 patent/WO2008001036A2/en active Application Filing
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US3888863A (en) * | 1970-04-14 | 1975-06-10 | Hoechst Ag | Benzoxanthene and benzothioxanthene dyestuffs and process for their manufacture |
US4242139A (en) * | 1978-02-03 | 1980-12-30 | Hoechst Aktiengesellschaft | Water soluble benzoxanthene dyestuffs for fluorescent inks |
US20060107869A1 (en) * | 2003-07-10 | 2006-05-25 | Dystar Textilf Deutschland Kg | Inks for digital textile printing with reactive yellow fluorescent dyes |
Cited By (15)
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US9029442B2 (en) | 2010-05-25 | 2015-05-12 | Sicpa Holding Sa | Polymer-bonded perylene dyes and compositions containing same |
US8859688B2 (en) | 2011-05-25 | 2014-10-14 | Sicpa Holding Sa | Polymer-bonded quaterrylene and/or terrylene dyes and compositions containing same |
US9249320B2 (en) | 2011-11-10 | 2016-02-02 | Sicpa Holding Sa | Polymer-bonded polycyclic aromatic hydrocarbons having nitrogen containing substituents |
US9062207B2 (en) | 2011-11-23 | 2015-06-23 | Sicpa Holding Sa | Polycyclic aromatic hydrocarbon compounds containing an S atom or S(═O)2 group in their basic structure |
JP2015509987A (en) * | 2011-11-23 | 2015-04-02 | シクパ ホルディング ソシエテ アノニムSicpa Holding Sa | Polycyclic aromatic compounds containing S atoms or S (= O) 2 groups and their use as dyes |
CN103958522A (en) * | 2011-11-23 | 2014-07-30 | 锡克拜控股有限公司 | Polycyclic aromatic compounds containing an S atom or S(=O)2 group and their use as dyes |
WO2013075980A1 (en) * | 2011-11-23 | 2013-05-30 | Sicpa Holding Sa | Polycyclic aromatic compounds containing an s atom or s(=0)2 group and their use as dyes |
US9505869B2 (en) | 2011-11-23 | 2016-11-29 | Sicpa Holding Sa | Polycyclic aromatic hydrocarbon compounds containing an S atom or S(=O)2 group in their basic structure |
WO2014105493A1 (en) * | 2012-12-28 | 2014-07-03 | Ecolab Usa Inc. | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
JP2016512996A (en) * | 2012-12-28 | 2016-05-12 | エコラブ ユーエスエイ インク | Tagged treated polymer containing the same for use in fluorescent monomers and industrial water systems |
US9751789B2 (en) | 2012-12-28 | 2017-09-05 | Ecolab Usa Inc. | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
EP3275844A1 (en) | 2012-12-28 | 2018-01-31 | Ecolab USA Inc. | Fluorescent monomers for the preparation of tagged treatment polymers useful in industrial water systems |
US10323112B2 (en) | 2012-12-28 | 2019-06-18 | Ecolab Usa Inc. | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
CN105143153A (en) * | 2013-03-18 | 2015-12-09 | 巴斯夫欧洲公司 | Perylenemonoimide and naphthalenemonoimide derivatives and their use in dye-sensitized solar cells |
WO2022059311A1 (en) * | 2020-09-15 | 2022-03-24 | コニカミノルタ株式会社 | Benzothioxanthene compound, resin particles, and fluorescent immunostaining reagent |
Also Published As
Publication number | Publication date |
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GB2450661B (en) | 2011-09-14 |
GB2450661A (en) | 2008-12-31 |
GB0612784D0 (en) | 2006-08-09 |
GB0819432D0 (en) | 2008-12-03 |
WO2008001036A3 (en) | 2008-06-19 |
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