CA2461751A1 - Use of a dyestuff for ink jet printing recording materials - Google Patents
Use of a dyestuff for ink jet printing recording materials Download PDFInfo
- Publication number
- CA2461751A1 CA2461751A1 CA002461751A CA2461751A CA2461751A1 CA 2461751 A1 CA2461751 A1 CA 2461751A1 CA 002461751 A CA002461751 A CA 002461751A CA 2461751 A CA2461751 A CA 2461751A CA 2461751 A1 CA2461751 A1 CA 2461751A1
- Authority
- CA
- Canada
- Prior art keywords
- acid red
- signifies
- phenyl
- unsubstituted
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000975 dye Substances 0.000 title claims abstract description 88
- 239000000463 material Substances 0.000 title claims abstract description 36
- 238000007641 inkjet printing Methods 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 139
- 238000007639 printing Methods 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 44
- 239000003960 organic solvent Substances 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 238000002844 melting Methods 0.000 claims description 15
- 230000008018 melting Effects 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 239000012530 fluid Substances 0.000 claims description 8
- 229910006069 SO3H Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical group 0.000 claims description 7
- 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 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- IHZXTIBMKNSJCJ-UHFFFAOYSA-N 3-{[(4-{[4-(dimethylamino)phenyl](4-{ethyl[(3-sulfophenyl)methyl]amino}phenyl)methylidene}cyclohexa-2,5-dien-1-ylidene)(ethyl)azaniumyl]methyl}benzene-1-sulfonate Chemical compound C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 IHZXTIBMKNSJCJ-UHFFFAOYSA-N 0.000 claims description 2
- XRBNWBONDUAVJJ-UHFFFAOYSA-N 4,5-dihydroxy-3-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OC1=C(C(=CC2=CC(=CC(=C12)O)S(=O)(=O)O)S(=O)(=O)O)N=NC1=CC=C(C2=CC=CC=C12)S(=O)(=O)O XRBNWBONDUAVJJ-UHFFFAOYSA-N 0.000 claims description 2
- RJZLMBIYRSBCDQ-UHFFFAOYSA-N 6-amino-5-[[2-[ethyl(phenyl)sulfamoyl]phenyl]diazenyl]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound CCN(C1=CC=CC=C1)S(=O)(=O)C1=CC=CC=C1N=NC1=C(N)C=CC2=C1C(O)=CC(=C2)S(O)(=O)=O RJZLMBIYRSBCDQ-UHFFFAOYSA-N 0.000 claims description 2
- GXEAXHYQKZAJGB-UHFFFAOYSA-L acid red 29 Chemical compound [Na+].[Na+].OC1=C2C(O)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 GXEAXHYQKZAJGB-UHFFFAOYSA-L 0.000 claims description 2
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 claims description 2
- JBBPTUVOZCXCSU-UHFFFAOYSA-L dipotassium;2',4',5',7'-tetrabromo-4,7-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [K+].[K+].O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(Br)=C([O-])C(Br)=C1OC1=C(Br)C([O-])=C(Br)C=C21 JBBPTUVOZCXCSU-UHFFFAOYSA-L 0.000 claims 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 claims description 2
- MHEPHJHRLWJBBX-UHFFFAOYSA-L disodium 4-hydroxy-5-[(4-methylphenyl)sulfonylamino]-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC2=C3C(=CC(=C2)S(=O)(=O)[O-])C=C(C(=C3[O-])N=NC4=CC=CC=C4)S(=O)(=O)O.[Na+].[Na+] MHEPHJHRLWJBBX-UHFFFAOYSA-L 0.000 claims description 2
- CZWHGIACASUWJC-UHFFFAOYSA-L disodium 5-acetamido-3-[(4-dodecylphenyl)diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].CCCCCCCCCCCCc1ccc(cc1)N=Nc1c(O)c2c(NC(C)=O)cc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O CZWHGIACASUWJC-UHFFFAOYSA-L 0.000 claims description 2
- LGWXIBBJZQOXSO-UHFFFAOYSA-L disodium 5-acetamido-4-hydroxy-3-[(2-methylphenyl)diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1C LGWXIBBJZQOXSO-UHFFFAOYSA-L 0.000 claims description 2
- LQJVOKWHGUAUHK-UHFFFAOYSA-L disodium 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(N)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 LQJVOKWHGUAUHK-UHFFFAOYSA-L 0.000 claims description 2
- CHVCXJYKVWHEBR-UHFFFAOYSA-L disodium 6-[(2-methoxyphenyl)diazenyl]-4-[(4-methylphenyl)sulfonylamino]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC2=C3C(=CC(=C2)S(=O)(=O)[O-])C=C(C(=C3[O-])N=NC4=CC=CC=C4OC)S(=O)(=O)O.[Na+].[Na+] CHVCXJYKVWHEBR-UHFFFAOYSA-L 0.000 claims description 2
- GCUHLYDQBADSHR-UHFFFAOYSA-L disodium 6-[(2-methylphenyl)diazenyl]-4-[(4-methylphenyl)sulfonylamino]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC2=C3C(=CC(=C2)S(=O)(=O)[O-])C=C(C(=C3[O-])N=NC4=CC=CC=C4C)S(=O)(=O)O.[Na+].[Na+] GCUHLYDQBADSHR-UHFFFAOYSA-L 0.000 claims description 2
- NJHFCEDUNPPBHI-UHFFFAOYSA-L disodium 6-[(4-cyclohexyl-2-methylphenyl)diazenyl]-4-[(4-methylphenyl)sulfonylamino]-5-oxido-7-sulfonaphthalene-2-sulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC2=C3C(=CC(=C2)S(=O)(=O)[O-])C=C(C(=C3[O-])N=NC4=C(C=C(C=C4)C5CCCCC5)C)S(=O)(=O)O.[Na+].[Na+] NJHFCEDUNPPBHI-UHFFFAOYSA-L 0.000 claims description 2
- XHWOCFKPINOVST-UHFFFAOYSA-L disodium 6-amino-5-[(4-amino-2-sulfonatophenyl)diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Nc1ccc(N=Nc2c(N)ccc3cc(cc(O)c23)S([O-])(=O)=O)c(c1)S([O-])(=O)=O XHWOCFKPINOVST-UHFFFAOYSA-L 0.000 claims description 2
- OOYIOIOOWUGAHD-UHFFFAOYSA-L disodium;2',4',5',7'-tetrabromo-4,5,6,7-tetrachloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(Br)=C([O-])C(Br)=C1OC1=C(Br)C([O-])=C(Br)C=C21 OOYIOIOOWUGAHD-UHFFFAOYSA-L 0.000 claims description 2
- RAGZEDHHTPQLAI-UHFFFAOYSA-L disodium;2',4',5',7'-tetraiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C([O-])C(I)=C1OC1=C(I)C([O-])=C(I)C=C21 RAGZEDHHTPQLAI-UHFFFAOYSA-L 0.000 claims description 2
- AHSJNHONMVUMLK-UHFFFAOYSA-L disodium;4',5'-diiodo-3-oxospiro[2-benzofuran-1,9'-xanthene]-3',6'-diolate Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC=C([O-])C(I)=C1OC1=C(I)C([O-])=CC=C21 AHSJNHONMVUMLK-UHFFFAOYSA-L 0.000 claims description 2
- QGAYMQGSQUXCQO-UHFFFAOYSA-L eosin b Chemical compound [Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC([N+]([O-])=O)=C([O-])C(Br)=C1OC1=C2C=C([N+]([O-])=O)C([O-])=C1Br QGAYMQGSQUXCQO-UHFFFAOYSA-L 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 claims description 2
- OPNKLROVOROGDY-UHFFFAOYSA-N sodium 3-[(4-formylphenyl)diazenyl]-4,5-dihydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=CC(=CC=C1C=O)N=NC2=C(C3=C(C=C(C=C3C=C2S(=O)(=O)O)S(=O)(=O)O)O)O.[Na+] OPNKLROVOROGDY-UHFFFAOYSA-N 0.000 claims description 2
- FZOKKUPFFREJLO-UHFFFAOYSA-N sodium 4,5-dihydroxy-3-[(4-nitrophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound C1=CC(=CC=C1N=NC2=C(C3=C(C=C(C=C3C=C2S(=O)(=O)O)S(=O)(=O)O)O)O)[N+](=O)[O-].[Na+] FZOKKUPFFREJLO-UHFFFAOYSA-N 0.000 claims description 2
- GVLHHJPRNMDLLL-UHFFFAOYSA-M sodium 7-amino-8-[[4-chloro-2-(trifluoromethyl)phenyl]diazenyl]-3-sulfonaphthalen-1-olate Chemical compound NC1=CC=C2C=C(C=C(O)C2=C1N=NC1=CC=C(Cl)C=C1C(F)(F)F)S(=O)(=O)O[Na] GVLHHJPRNMDLLL-UHFFFAOYSA-M 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- YEOUFHBJWTZWCZ-UHFFFAOYSA-M sulforhodamine G Chemical compound [Na+].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O YEOUFHBJWTZWCZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 235000010980 cellulose Nutrition 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- SWYAODARJIJAKL-UHFFFAOYSA-L disodium 3-[[4-[1-[4-[(1,7-dihydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]cyclohexyl]-2-methylphenyl]diazenyl]-4,6-dihydroxynaphthalene-2-sulfonate Chemical compound [Na+].[Na+].Cc1cc(ccc1N=Nc1c(O)c2cc(O)ccc2cc1S([O-])(=O)=O)C1(CCCCC1)c1ccc(N=Nc2c(O)c3cc(O)ccc3cc2S([O-])(=O)=O)c(C)c1 SWYAODARJIJAKL-UHFFFAOYSA-L 0.000 claims 1
- 238000004043 dyeing Methods 0.000 claims 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-M sodium 2-[3-(2-methylanilino)-6-(2-methyl-4-sulfonatoanilino)xanthen-10-ium-9-yl]benzoate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C([O-])=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-M 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 12
- 239000000758 substrate Substances 0.000 abstract description 12
- 239000004033 plastic Substances 0.000 abstract description 11
- 229920003023 plastic Polymers 0.000 abstract description 11
- 239000002985 plastic film Substances 0.000 abstract description 9
- 229920006255 plastic film Polymers 0.000 abstract description 9
- 239000004753 textile Substances 0.000 abstract description 9
- 239000000976 ink Substances 0.000 description 51
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 28
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 239000000123 paper Substances 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000003086 colorant Substances 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 7
- 229950006389 thiodiglycol Drugs 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 229940043375 1,5-pentanediol Drugs 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- -1 keto alcohols Chemical class 0.000 description 5
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 4
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IDVNZMQMDGSYNQ-UHFFFAOYSA-M sodium 2-(naphthalen-1-yldiazenyl)-5-sulfonaphthalen-1-olate Chemical compound [Na+].Oc1c(ccc2c(cccc12)S([O-])(=O)=O)N=Nc1cccc2ccccc12 IDVNZMQMDGSYNQ-UHFFFAOYSA-M 0.000 description 4
- 239000003021 water soluble solvent Substances 0.000 description 4
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 description 3
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 3
- VKBVRNHODPFVHK-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]ethanol Chemical compound CCN(CC)CCOCCO VKBVRNHODPFVHK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 3
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 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
- 238000011033 desalting Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 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
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 1
- BWSQKOKULIALEW-UHFFFAOYSA-N 2-[2-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[2-(piperidin-3-ylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound FC1=C(C=C(C=C1)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CNCCC1)C(F)(F)F BWSQKOKULIALEW-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 1
- VNWVMZDJPMCAKD-UHFFFAOYSA-N 3-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1O VNWVMZDJPMCAKD-UHFFFAOYSA-N 0.000 description 1
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- DBZJJPROPLPMSN-UHFFFAOYSA-N bromoeosin Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C(O)C(Br)=C1OC1=C(Br)C(O)=C(Br)C=C21 DBZJJPROPLPMSN-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- JCSGAUKCDAVARS-SOUFLCLCSA-N chembl2106517 Chemical compound C1([C@@H](O)[C@H]2C3)=CC=CC(O)=C1C(=O)C2=C(O)[C@@]1(O)[C@@H]3[C@H](N(C)C)C(O)=C(C(N)=O)C1=O JCSGAUKCDAVARS-SOUFLCLCSA-N 0.000 description 1
- ZJKLNUHASXGERK-UHFFFAOYSA-M chembl3185301 Chemical compound [Na+].NC1=CC=C2C=C(S([O-])(=O)=O)C=C(O)C2=C1N=NC1=CC=CC=C1C(F)(F)F ZJKLNUHASXGERK-UHFFFAOYSA-M 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 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
- DMYYMROEUDSFIN-UHFFFAOYSA-L disodium 3-hydroxy-4-[[2-methyl-4-[(2-methylphenyl)diazenyl]phenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Cc1ccccc1N=Nc1ccc(N=Nc2c(O)c(cc3cc(ccc23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)c1 DMYYMROEUDSFIN-UHFFFAOYSA-L 0.000 description 1
- YCMOBGSVZYLYBZ-UHFFFAOYSA-L disodium 5-[[4-[4-[(2-amino-8-hydroxy-6-sulfonatonaphthalen-1-yl)diazenyl]phenyl]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound NC1=CC=C2C=C(C=C(O)C2=C1N=NC1=CC=C(C=C1)C1=CC=C(C=C1)N=NC1=CC=C(O)C(=C1)C(=O)O[Na])S(=O)(=O)O[Na] YCMOBGSVZYLYBZ-UHFFFAOYSA-L 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000001471 micro-filtration Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SIMWTRCFFSTNMG-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[4-(2-hydroxyacetyl)piperazin-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCN(C(=O)CO)CC1 SIMWTRCFFSTNMG-AWEZNQCLSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- UWMZZSRDUVJJDP-UHFFFAOYSA-N sodium 4-[[9-(2-carboxyphenyl)-6-(2-methylanilino)xanthen-10-ium-3-yl]amino]-3-methylbenzenesulfonate Chemical compound [Na+].Cc1ccccc1Nc1ccc2c(-c3ccccc3C(O)=O)c3ccc(Nc4ccc(cc4C)S([O-])(=O)=O)cc3[o+]c2c1 UWMZZSRDUVJJDP-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
-
- 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
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
- C09B29/28—Amino naphthols
- C09B29/30—Amino naphtholsulfonic acid
-
- 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
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
-
- 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
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
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)
- Coloring (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0130309A GB0130309D0 (en) | 2001-12-19 | 2001-12-19 | Organic compounds |
| GB0130309.8 | 2001-12-19 | ||
| GB0225997A GB0225997D0 (en) | 2002-11-07 | 2002-11-07 | Use of dyestuff for printing recording materials |
| GB0225997.6 | 2002-11-07 | ||
| PCT/IB2002/005474 WO2003052007A1 (en) | 2001-12-19 | 2002-12-18 | Use of a dyestuff for ink jet printing recording materials . |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461751A1 true CA2461751A1 (en) | 2003-06-26 |
Family
ID=26246883
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461751A Abandoned CA2461751A1 (en) | 2001-12-19 | 2002-12-18 | Use of a dyestuff for ink jet printing recording materials |
| CA002461750A Abandoned CA2461750A1 (en) | 2001-12-19 | 2002-12-18 | Acidic mono azo dyestuffs |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461750A Abandoned CA2461750A1 (en) | 2001-12-19 | 2002-12-18 | Acidic mono azo dyestuffs |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7153332B2 (enExample) |
| EP (2) | EP1463781B1 (enExample) |
| JP (2) | JP2005513188A (enExample) |
| KR (2) | KR20040075888A (enExample) |
| CN (2) | CN1283731C (enExample) |
| AT (1) | ATE393802T1 (enExample) |
| AU (2) | AU2002348731A1 (enExample) |
| BR (2) | BR0215076A (enExample) |
| CA (2) | CA2461751A1 (enExample) |
| DE (1) | DE60226346T2 (enExample) |
| ES (1) | ES2302853T3 (enExample) |
| MX (2) | MXPA04003488A (enExample) |
| PT (1) | PT1463781E (enExample) |
| TW (2) | TW200301288A (enExample) |
| WO (2) | WO2003052007A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20040075888A (ko) * | 2001-12-19 | 2004-08-30 | 클라리언트 파이넌스 (비브이아이)리미티드 | 산성 모노 아조 염료 |
| JP2005352363A (ja) * | 2004-06-14 | 2005-12-22 | Ricoh Co Ltd | 液体現像剤、液体現像剤収容器、および画像形成方法、画像形成装置 |
| BRPI0517790A (pt) * | 2004-11-12 | 2008-10-21 | Neurochem Int Ltd | métodos e composições fluoradas para tratar doenças relacionadas à amilóide |
| GB0505879D0 (en) * | 2005-03-22 | 2005-04-27 | Ten Cate Advanced Textiles Bv | Composition for continuous inkjet finishing of a textile article |
| CN100387656C (zh) * | 2005-11-01 | 2008-05-14 | 吴江市罗林染化有限公司 | 直接混纺紫染料的制备工艺 |
| MX2008012702A (es) * | 2006-04-07 | 2008-10-15 | Clariant Finance Bvi Ltd | Colorantes acidos. |
| US7387665B2 (en) * | 2006-04-12 | 2008-06-17 | E.I. Du Pont De Nemours And Company | Inkjet ink and ink set |
| EP2035506B1 (en) * | 2006-06-25 | 2010-12-01 | Clariant Finance (BVI) Limited | Acid dyes |
| US20100112306A1 (en) * | 2006-09-09 | 2010-05-06 | Fujifilm Imaging Colorants Limited | Process, Compound, Ink and Use |
| US8496743B2 (en) * | 2010-03-18 | 2013-07-30 | Seiko Epson Corporation | Ink composition |
| JP2013091723A (ja) * | 2011-10-26 | 2013-05-16 | Sumitomo Chemical Co Ltd | 化合物 |
| US10894896B2 (en) | 2016-12-28 | 2021-01-19 | Seiko Epson Corporation | Ink jet ink composition for textile printing, ink set, and recording method |
| EP3342927B1 (en) | 2016-12-28 | 2019-08-14 | Seiko Epson Corporation | Ink jet ink composition for textile printing, ink set, and recording method |
| CN106893355A (zh) * | 2017-01-10 | 2017-06-27 | 泉州市希姆色彩研究院有限公司 | 一种高水牢度的分散黑染料及其制备方法 |
| JP2019060051A (ja) | 2017-09-27 | 2019-04-18 | セイコーエプソン株式会社 | 記録方法 |
| JP7017054B2 (ja) * | 2017-09-29 | 2022-02-08 | セイコーエプソン株式会社 | インクジェット捺染インク、インクジェット捺染インクセットおよび捺染方法 |
| JP2019137793A (ja) | 2018-02-13 | 2019-08-22 | セイコーエプソン株式会社 | 捺染インクジェットインク組成物セット及び記録方法 |
| CN109824607B (zh) * | 2019-04-02 | 2022-12-09 | 上海应用技术大学 | 一种双偶氮化合物重氮组分的制备方法 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE606364A (enExample) | 1960-07-22 | |||
| DE2061760B2 (de) | 1970-12-15 | 1974-07-25 | Bayer Ag, 5090 Leverkusen | Konzentrierte wäßrige Lösungen metallfreier anionischer Farbstoffe |
| CA985675A (en) | 1971-04-07 | 1976-03-16 | Ciba-Geigy Ag | Azo dyestuffs, their manufacture and use |
| GB1550651A (en) * | 1976-01-16 | 1979-08-15 | Ici Ltd | Monoazo dyes |
| GB1566804A (en) | 1976-07-28 | 1980-05-08 | Ici Ltd | Wet transfer printing process for the colouration of cellulose textile materials |
| DE2712170C2 (de) * | 1977-03-19 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Azofarbstoffe |
| JPS55150370A (en) | 1979-05-14 | 1980-11-22 | Fuji Photo Film Co Ltd | Recording method by ink jet |
| ATE30176T1 (de) * | 1983-05-25 | 1987-10-15 | Ciba Geigy Ag | Verfahren zum trichromie-faerben oder -bedrucken. |
| US4626284A (en) * | 1983-10-08 | 1986-12-02 | Mitsubishi Chemical Industries Ltd. | Recording liquid |
| DE3416087A1 (de) | 1984-04-30 | 1985-10-31 | Klöckner-Humboldt-Deutz AG, 5000 Köln | Gekuehlte turbinenschaufel |
| US4554181A (en) | 1984-05-07 | 1985-11-19 | The Mead Corporation | Ink jet recording sheet having a bicomponent cationic recording surface |
| GB8421551D0 (en) * | 1984-08-24 | 1984-09-26 | Ici Plc | Water-soluble dye |
| US4849770A (en) | 1985-12-13 | 1989-07-18 | Canon Kabushiki Kaisha | Ink for use in ink jet and ink jet printing method using the same |
| US4956230A (en) | 1987-04-13 | 1990-09-11 | Minnesota Mining And Manufacturing Company | Ink receptive transparency sheet |
| US5227477A (en) * | 1988-06-14 | 1993-07-13 | Sandoz Ltd. | Dyes having one or two 2,4- or 4,6-dichloro-5-cyanopyrimidyl groups linked through bridging radicals containing at least two nitrogen atoms to chloro-1,3,5-triazinyl groups |
| DE3918653C2 (de) | 1988-06-14 | 2003-01-16 | Clariant Finance Bvi Ltd | Chromophore Verbindung mit heterocyclischem Reaktivrest |
| US4935307A (en) * | 1988-10-21 | 1990-06-19 | Minnesota Mining And Manufacturing Company | Transparent coatings for graphics applications |
| US4963189A (en) | 1989-08-24 | 1990-10-16 | Hewlett-Packard Company | Waterfast ink formulations with a novel series of anionic dyes containing two or more carboxyl groups |
| US5062892A (en) | 1989-10-27 | 1991-11-05 | Hewlett-Packard Company | Ink additives for improved ink-jet performance |
| US5006862A (en) * | 1989-10-27 | 1991-04-09 | Hewlett-Packard Company | Fixation of reactive dyes to paper by ink-jet printing |
| US5219928A (en) * | 1990-10-24 | 1993-06-15 | Minnesota Mining And Manufacturing Company | Transparent liquid absorbent materials |
| US5134198A (en) * | 1990-10-24 | 1992-07-28 | Minnesota Mining And Manufacturing Company | Transparent liquid absorbent materials |
| US5756212A (en) | 1994-04-14 | 1998-05-26 | Sihl Gmbh | Recording material |
| DE4438177A1 (de) * | 1994-10-26 | 1996-05-02 | Bayer Ag | Farbstoffe für Drucktinten |
| DE4441960A1 (de) | 1994-11-25 | 1996-05-30 | Basf Ag | Farbstoffpräparationen |
| DE4446551C1 (de) * | 1994-12-24 | 1996-03-14 | Renker Gmbh & Co Kg | Wasserfestes Aufzeichnungsmaterial für Tintenstrahldruck |
| JPH10297078A (ja) | 1997-04-28 | 1998-11-10 | Nisshinbo Ind Inc | インクジェット記録シート |
| GB9710611D0 (en) | 1997-05-23 | 1997-07-16 | Clariant Int Ltd | New disazo dyestuffs |
| GB9722395D0 (en) | 1997-10-24 | 1997-12-24 | Zeneca Ltd | Process |
| GB9811548D0 (en) | 1998-05-30 | 1998-07-29 | Clariant Int Ltd | New monoazo dyestuffs |
| GB9914544D0 (en) | 1999-06-23 | 1999-08-25 | Zeneca Ltd | Compositions |
| EP1268675B1 (en) * | 2000-03-28 | 2003-10-22 | Clariant Finance (BVI) Limited | Use of a dye composition for inkjet printing |
| ATE213759T1 (de) * | 2000-05-30 | 2002-03-15 | Ilford Imaging Ch Gmbh | Azofarbstoffe, deren herstellung und verwendung |
| DE10049200A1 (de) * | 2000-10-05 | 2002-04-11 | Clariant Gmbh | Verfahren zur Herstellung von Azofarbmitteln |
| GB0029468D0 (en) * | 2000-12-04 | 2001-01-17 | Clariant Int Ltd | Use of disazo compounds |
| GB0103240D0 (en) * | 2001-02-09 | 2001-03-28 | Clariant Int Ltd | Organic compounds |
| CN1322063C (zh) * | 2001-04-20 | 2007-06-20 | 克莱里安特财务(Bvi)有限公司 | 纤维－反应性单偶氮基染料 |
| KR20040075888A (ko) * | 2001-12-19 | 2004-08-30 | 클라리언트 파이넌스 (비브이아이)리미티드 | 산성 모노 아조 염료 |
| US6764541B1 (en) * | 2003-04-24 | 2004-07-20 | Xerox Corporation | Colorant compositions |
-
2002
- 2002-12-18 KR KR10-2004-7009525A patent/KR20040075888A/ko not_active Ceased
- 2002-12-18 AT AT02781678T patent/ATE393802T1/de not_active IP Right Cessation
- 2002-12-18 JP JP2003552876A patent/JP2005513188A/ja not_active Withdrawn
- 2002-12-18 JP JP2003552877A patent/JP2005513189A/ja not_active Withdrawn
- 2002-12-18 EP EP02781678A patent/EP1463781B1/en not_active Expired - Lifetime
- 2002-12-18 MX MXPA04003488A patent/MXPA04003488A/es active IP Right Grant
- 2002-12-18 KR KR10-2004-7009624A patent/KR20040076258A/ko not_active Ceased
- 2002-12-18 CN CNB02825564XA patent/CN1283731C/zh not_active Expired - Fee Related
- 2002-12-18 WO PCT/IB2002/005474 patent/WO2003052007A1/en not_active Ceased
- 2002-12-18 CA CA002461751A patent/CA2461751A1/en not_active Abandoned
- 2002-12-18 MX MXPA04003489A patent/MXPA04003489A/es active IP Right Grant
- 2002-12-18 BR BR0215076-0A patent/BR0215076A/pt not_active IP Right Cessation
- 2002-12-18 AU AU2002348731A patent/AU2002348731A1/en not_active Abandoned
- 2002-12-18 WO PCT/IB2002/005473 patent/WO2003052006A1/en not_active Ceased
- 2002-12-18 TW TW091136493A patent/TW200301288A/zh unknown
- 2002-12-18 PT PT02781678T patent/PT1463781E/pt unknown
- 2002-12-18 US US10/498,856 patent/US7153332B2/en not_active Expired - Fee Related
- 2002-12-18 DE DE60226346T patent/DE60226346T2/de not_active Expired - Fee Related
- 2002-12-18 ES ES02781678T patent/ES2302853T3/es not_active Expired - Lifetime
- 2002-12-18 US US10/499,168 patent/US7097702B2/en not_active Expired - Fee Related
- 2002-12-18 CA CA002461750A patent/CA2461750A1/en not_active Abandoned
- 2002-12-18 EP EP02785861A patent/EP1495079A1/en not_active Withdrawn
- 2002-12-18 BR BR0215015-8A patent/BR0215015A/pt not_active IP Right Cessation
- 2002-12-18 TW TW091136491A patent/TWI278493B/zh not_active IP Right Cessation
- 2002-12-18 AU AU2002351148A patent/AU2002351148A1/en not_active Abandoned
- 2002-12-18 CN CNB028251539A patent/CN100340619C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN100340619C (zh) | 2007-10-03 |
| DE60226346T2 (de) | 2008-08-14 |
| BR0215076A (pt) | 2004-11-09 |
| TWI278493B (en) | 2007-04-11 |
| AU2002351148A1 (en) | 2003-06-30 |
| EP1463781B1 (en) | 2008-04-30 |
| KR20040075888A (ko) | 2004-08-30 |
| KR20040076258A (ko) | 2004-08-31 |
| TW200301771A (en) | 2003-07-16 |
| WO2003052006A1 (en) | 2003-06-26 |
| WO2003052007A1 (en) | 2003-06-26 |
| ATE393802T1 (de) | 2008-05-15 |
| JP2005513189A (ja) | 2005-05-12 |
| US20050172856A1 (en) | 2005-08-11 |
| CN1604944A (zh) | 2005-04-06 |
| JP2005513188A (ja) | 2005-05-12 |
| MXPA04003489A (es) | 2004-07-30 |
| US20050120495A1 (en) | 2005-06-09 |
| BR0215015A (pt) | 2004-11-09 |
| US7153332B2 (en) | 2006-12-26 |
| EP1495079A1 (en) | 2005-01-12 |
| EP1463781A1 (en) | 2004-10-06 |
| DE60226346D1 (de) | 2008-06-12 |
| CA2461750A1 (en) | 2003-06-26 |
| MXPA04003488A (es) | 2004-07-30 |
| TW200301288A (en) | 2003-07-01 |
| CN1606603A (zh) | 2005-04-13 |
| US7097702B2 (en) | 2006-08-29 |
| HK1076480A1 (zh) | 2006-01-20 |
| CN1283731C (zh) | 2006-11-08 |
| ES2302853T3 (es) | 2008-08-01 |
| PT1463781E (pt) | 2008-07-03 |
| AU2002348731A1 (en) | 2003-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1463781B1 (en) | Use of a dyestuff for ink jet printing recording materials | |
| WO2007132151A1 (en) | Trisazo dyes, compositions and ink jet printing processes | |
| WO2010041065A1 (en) | Disazo compounds and their use in ink-jet printing | |
| EP2024442A1 (en) | Trisazo compounds, compositions and ink jet printing processes | |
| EP1563011B1 (en) | Mono azo dyes | |
| EP2344589A2 (en) | Disazo compounds and their use in ink-jet printing | |
| EP1704187A1 (en) | Acidic monoazo dyestuffs | |
| GB2469191A (en) | Polyazo dyes and their use in inkjet printing | |
| JP3428178B2 (ja) | 記録液 | |
| EP1424368A1 (en) | Mono azo dyes | |
| WO2007045829A2 (en) | Yellow azo dyes for ink jet printing | |
| GB2440422A (en) | Arylazo, hydroxy and sulpho substituted 2-aryl-naphtho[1,2-d]imidazoles for use as dyes in ink jet printing | |
| HK1102132A (en) | Acidic mono azo dyestuffs | |
| WO2004033559A1 (en) | Monoazo compounds and inks containing them | |
| WO2004078859A1 (en) | Magenta metal chelate dyes and their use in ink-jet printers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |