CH678186A5 - - Google Patents
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- CH678186A5 CH678186A5 CH2190/89A CH219089A CH678186A5 CH 678186 A5 CH678186 A5 CH 678186A5 CH 2190/89 A CH2190/89 A CH 2190/89A CH 219089 A CH219089 A CH 219089A CH 678186 A5 CH678186 A5 CH 678186A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- 4alkyl
- so3h
- independently
- another
- Prior art date
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 104
- 239000001257 hydrogen Substances 0.000 claims abstract description 104
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 65
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 44
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical group 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 17
- 229910004727 OSO3H Inorganic materials 0.000 claims abstract description 15
- 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 claims abstract description 7
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims abstract description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims abstract description 4
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims abstract description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- -1 azomethine Chemical compound 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- 230000008878 coupling Effects 0.000 claims description 14
- 238000010168 coupling process Methods 0.000 claims description 14
- IAJCAZVXGKGAQK-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonitrile Chemical compound ClC1=NC(Cl)=C(C#N)C(Cl)=N1 IAJCAZVXGKGAQK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000001879 copper Chemical class 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 150000002790 naphthalenes Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 4
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001868 cobalt Chemical class 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 150000004961 triphenylmethanes Chemical class 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 238000004043 dyeing Methods 0.000 abstract description 49
- 229920000742 Cotton Polymers 0.000 abstract description 44
- 239000000463 material Substances 0.000 abstract description 14
- 230000001590 oxidative effect Effects 0.000 abstract description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 abstract description 7
- 239000000758 substrate Substances 0.000 abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract description 2
- 239000010985 leather Substances 0.000 abstract description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 abstract description 2
- 229920002647 polyamide Polymers 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 abstract description 2
- 150000004696 coordination complex Chemical group 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 32
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 150000001768 cations Chemical class 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 8
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000985 reactive dye Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001007 phthalocyanine dye Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229960001506 brilliant green Drugs 0.000 description 3
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 239000010981 turquoise Substances 0.000 description 3
- 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
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UYSRSLSTXYYNEW-UHFFFAOYSA-N NS(=O)(=O)S(O)(=O)=O Chemical compound NS(=O)(=O)S(O)(=O)=O UYSRSLSTXYYNEW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Chemical class 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000004700 cobalt complex Chemical class 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3820149 | 1988-06-14 | ||
| CN94105676A CN1056635C (zh) | 1988-06-14 | 1994-05-13 | 具有纤维反应性基团的发色化合物或其盐或其混合物在含羟基或含氮有机基质染色或印花中的应用 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH678186A5 true CH678186A5 (en:Method) | 1991-08-15 |
Family
ID=36829953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2190/89A CH678186A5 (en:Method) | 1988-06-14 | 1989-06-12 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JP2641943B2 (en:Method) |
| CN (1) | CN1056635C (en:Method) |
| AT (1) | AT398978B (en:Method) |
| CH (1) | CH678186A5 (en:Method) |
| DE (1) | DE3918653C2 (en:Method) |
| EG (1) | EG19298A (en:Method) |
| ES (1) | ES2016026A6 (en:Method) |
| FR (1) | FR2632651B1 (en:Method) |
| GB (1) | GB2219804B (en:Method) |
| HK (1) | HK134294A (en:Method) |
| IT (1) | IT1231922B (en:Method) |
| PT (1) | PT90839B (en:Method) |
| ZA (1) | ZA894538B (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9303266A (pt) * | 1992-08-14 | 1994-03-08 | Sandoz Ag | Compostos e seus sais ou misturas de fais compostos ou sais,processos para sua preparacao,e processo para tingimento ou estampagem de um substrato organico |
| DE4331386B4 (de) * | 1992-09-17 | 2006-02-16 | Clariant Finance (Bvi) Ltd. | Faserreaktive Monoazofarbstoffe |
| JP3657627B2 (ja) * | 1992-10-12 | 2005-06-08 | クラリアント ファイナンス （ビーブイアイ） リミティド | 繊維反応性アゾ染料化合物およびその製造法 |
| DE4304242A1 (de) * | 1993-02-12 | 1994-08-18 | Sandoz Ag | Phthalocyanin-Reaktivfarbstoffe |
| DE19529853A1 (de) * | 1995-08-14 | 1997-02-20 | Bayer Ag | Aluminium-Phthalocyanin-Reaktivfarbstoffe |
| DE19530198A1 (de) * | 1995-08-17 | 1997-02-20 | Sandoz Ag | Asymmetrische Triphendioxazin-Reaktivfarbstoffe |
| DE19911195A1 (de) * | 1999-03-13 | 2000-09-14 | Clariant Gmbh | Wasserlösliche rote Säurefarbstoffe, ihre Herstellung und Verwendung |
| DE19911536A1 (de) | 1999-03-16 | 2000-09-21 | Clariant Gmbh | Rote Säurefarbstoffe für den Tintenstrahldruck und Papiereinfärbung |
| ES2208575T3 (es) * | 2000-03-28 | 2004-06-16 | Clariant Finance (Bvi) Limited | Uso de una composicion de colorante para impresion por inyeccion de tinta. |
| JP2005513189A (ja) | 2001-12-19 | 2005-05-12 | クラリアント インターナショナル リミティド | 記録材料印刷のための色素の使用 |
| CN118271871A (zh) * | 2024-03-06 | 2024-07-02 | 迈得诺医疗科技集团有限公司 | 一种均三嗪型活性染料及其改性方法与应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3362948A (en) * | 1961-05-19 | 1968-01-09 | Ici Ltd | Monoazo dyestuffs containing both triazine and pyrimidine groups |
| CH441563A (de) * | 1964-10-12 | 1967-08-15 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| GB1247186A (en) * | 1968-02-27 | 1971-09-22 | Ici Ltd | New reactive dyestuffs |
| US4007164A (en) * | 1968-03-19 | 1977-02-08 | Bayer Aktiengesellschaft | Azo dyestuffs containing 6-fluoro-pyrimidinyl 4-reactive group |
| GB1250487A (en:Method) * | 1968-05-30 | 1971-10-20 | ||
| GB1320921A (en) * | 1970-03-02 | 1973-06-20 | Ici Ltd | Fibre-reactive dyestuffs |
| GB1384749A (en) * | 1972-09-06 | 1975-02-19 | Ici Ltd | Reactive dyestuffs |
| GB1492414A (en) * | 1975-07-02 | 1977-11-16 | Ici Ltd | Fibre reactive monoazo dyes |
| DE2603670A1 (de) * | 1976-01-31 | 1977-08-04 | Bayer Ag | Reaktivfarbstoffe |
| DE2607028A1 (de) * | 1976-02-20 | 1977-08-25 | Bayer Ag | Reaktivfarbstoffe |
| DE2706417A1 (de) * | 1976-02-27 | 1977-09-01 | Sandoz Ag | Monoazoverbindungen enthaltend einen pyrimidinrest |
| DE2749597C2 (de) * | 1977-11-05 | 1986-04-24 | Bayer Ag, 5090 Leverkusen | Metallkomplex-Reaktivfarbstoffe |
| DE3545555A1 (de) * | 1984-12-31 | 1986-07-10 | Sandoz-Patent-GmbH, 7850 Lörrach | Faserreaktive monoazoverbindungen |
-
1989
- 1989-06-08 DE DE3918653A patent/DE3918653C2/de not_active Expired - Fee Related
- 1989-06-12 GB GB8913469A patent/GB2219804B/en not_active Expired - Lifetime
- 1989-06-12 FR FR898907841A patent/FR2632651B1/fr not_active Expired - Lifetime
- 1989-06-12 CH CH2190/89A patent/CH678186A5/de not_active IP Right Cessation
- 1989-06-12 PT PT90839A patent/PT90839B/pt not_active IP Right Cessation
- 1989-06-13 EG EG28889A patent/EG19298A/xx active
- 1989-06-13 AT AT0144389A patent/AT398978B/de not_active IP Right Cessation
- 1989-06-13 JP JP1148516A patent/JP2641943B2/ja not_active Expired - Fee Related
- 1989-06-13 IT IT8948077A patent/IT1231922B/it active
- 1989-06-14 ZA ZA894538A patent/ZA894538B/xx unknown
- 1989-06-14 ES ES8902091A patent/ES2016026A6/es not_active Expired - Lifetime
-
1994
- 1994-05-13 CN CN94105676A patent/CN1056635C/zh not_active Expired - Fee Related
- 1994-12-01 HK HK134294A patent/HK134294A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2016026A6 (es) | 1990-10-01 |
| ATA144389A (de) | 1994-07-15 |
| IT8948077A0 (it) | 1989-06-13 |
| DE3918653A1 (de) | 1989-12-21 |
| JPH0234667A (ja) | 1990-02-05 |
| FR2632651A1 (fr) | 1989-12-15 |
| GB2219804B (en) | 1992-04-01 |
| AT398978B (de) | 1995-02-27 |
| CN1098121A (zh) | 1995-02-01 |
| DE3918653C2 (de) | 2003-01-16 |
| HK134294A (en) | 1994-12-09 |
| IT1231922B (it) | 1992-01-15 |
| PT90839A (pt) | 1989-12-29 |
| GB2219804A (en) | 1989-12-20 |
| EG19298A (en) | 1996-02-29 |
| JP2641943B2 (ja) | 1997-08-20 |
| FR2632651B1 (fr) | 1990-11-30 |
| GB8913469D0 (en) | 1989-08-02 |
| ZA894538B (en) | 1991-02-27 |
| PT90839B (pt) | 1994-12-30 |
| CN1056635C (zh) | 2000-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NV | New agent |
Representative=s name: SANDOZ TECHNOLOGIE AG |
|
| PUE | Assignment |
Owner name: SANDOZ AG TRANSFER- CLARIANT FINANCE (BVI) LIMITED |
|
| NV | New agent |
Representative=s name: CLARIANT INTERNATIONAL LTD. |
|
| PL | Patent ceased |