US20080244839A1 - Mixtures Of Reactive Dyes And Their Use - Google Patents
Mixtures Of Reactive Dyes And Their Use Download PDFInfo
- Publication number
- US20080244839A1 US20080244839A1 US10/592,888 US59288805A US2008244839A1 US 20080244839 A1 US20080244839 A1 US 20080244839A1 US 59288805 A US59288805 A US 59288805A US 2008244839 A1 US2008244839 A1 US 2008244839A1
- Authority
- US
- United States
- Prior art keywords
- dye
- formula
- halogen
- hal
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 239000000985 reactive dye Substances 0.000 title description 9
- 238000004043 dyeing Methods 0.000 claims abstract description 32
- 239000000835 fiber Substances 0.000 claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 24
- 238000007639 printing Methods 0.000 claims abstract description 15
- -1 phenylenemethylene Chemical group 0.000 claims description 46
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 26
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229920000742 Cotton Polymers 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 238000005507 spraying Methods 0.000 claims 1
- 229920002678 cellulose Polymers 0.000 abstract description 5
- 239000001913 cellulose Substances 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 111
- 150000003254 radicals Chemical class 0.000 description 29
- 239000000976 ink Substances 0.000 description 25
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
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- 239000000654 additive Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002562 thickening agent Substances 0.000 description 5
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- 229910004727 OSO3H Inorganic materials 0.000 description 4
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- 229910021538 borax Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 150000002170 ethers Chemical class 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 210000002268 wool Anatomy 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
- AVGVFDSUDIUXEU-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-3-one Chemical compound CCCCCCCCN1SCCC1=O AVGVFDSUDIUXEU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- 239000002202 Polyethylene glycol Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 125000004169 (C1-C6) alkyl 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
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- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 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
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative 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
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013535 sea water Substances 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
- 238000000926 separation method Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 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
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-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
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
- C09B67/0042—Mixtures containing two reactive dyes one of them being an azo dye
-
- 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
- C09B62/04—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 to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
- C09B67/0042—Mixtures containing two reactive dyes one of them being an azo dye
- C09B67/0044—Mixtures containing two reactive dyes one of them being an azo dye both having the reactive group directly attached to a heterocyclic system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
- C09B67/0057—Mixtures of two or more reactive disazo 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0055—Mixtures of two or more disazo dyes
- C09B67/0057—Mixtures of two or more reactive disazo dyes
- C09B67/0058—Mixtures of two or more reactive disazo dyes all the reactive groups are directly attached to a heterocyclic system
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/14—Wool
- D06P3/148—Wool using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
Definitions
- T 2 independently has the definition of X 2 , is a non-fibre-reactive substituent or is a fibre-reactive radical of formula
- R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and the corresponding radicals in the bridging member G each independently of the others, for example, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl and isobutyl, preferably methyl and ethyl and especially methyl.
- U there come into consideration, for example, —Cl, —Br, —F, —OSO 3 H, —SSO 3 H, OCO—CH 3 , —OPO 3 H 2 , —OCO—C 6 H 6 , —OSO 2 —C 1 -C 4 alkyl and —OSO 2 —N(C 1 -C 4 alkyl) 2 .
- U is a group of formula —Cl, —OSO 3 H, —SSO 3 H, —OCO—CH 3 , —OCO—C 6 H 6 or —OPO 3 H 2 , especially —Cl or —OSO 3 H and more especially —OSO 3 H.
- T 2 is preferably a non-fibre-reactive substituent or a fibre-reactive radical of formula (6a), (6b), (6c), (6d) or (6e).
- T 2 is preferably a radical of formula (6b), (6c), (6d) or (6e), especially of formula (6b), (6c) or (6d), and more especially of formula (6c), the definitions and preferred meanings given hereinbefore applying to the variables.
- Z is preferably vinyl or ⁇ -chloroethyl.
- Z is preferably vinyl or ⁇ -sulfatoethyl.
- T 2 is one of the above-mentioned fibre-reactive radicals.
- Hal in the fibre-reactive radicals of formulae (5d), (5e) and (6e) is preferably chlorine or bromine, especially bromine.
- the dye of formula (4) is preferably a dye of formula
- a dye of formula (1) to which special preference is given is a dye of formula
- the dye of formula (1) is, for example, a dye of formula
- the dye mixtures according to the invention can be prepared, for example, by mixing the individual dyes. Such a mixing process is carried out, for example, in suitable mills, for example ball mills or pin mills, and also in kneaders or mixers.
- the dyes used in the aqueous inks should preferably have a low salt content, that is to say they should have a total content of salts of less than 0.5% by weight, based on the weight of the dyes.
- Dyes that have relatively high salt contents as a result of their preparation and/or as a result of the subsequent addition of diluents can be salted out, for example, by membrane separation procedures, such as ultrafiltration, reverse osmosis or dialysis.
- the inks may comprise thickeners of natural or synthetic origin inter alia for the purpose of adjusting the viscosity.
- the inks may also comprise further additives, such as fluorinated polymers or telomers, e.g. polyethoxyperfluoroalcohols (Forafac® or Zonyl® products) in an amount of e.g. from 0.01 to 1% by weight, based on the total weight of the ink.
- fluorinated polymers or telomers e.g. polyethoxyperfluoroalcohols (Forafac® or Zonyl® products) in an amount of e.g. from 0.01 to 1% by weight, based on the total weight of the ink.
- inkjet printing individual droplets of the ink are sprayed onto a substrate in a controlled manner from a nozzle.
- the continuous inkjet method the droplets are produced continuously and any droplets not required for the printing are conveyed to a collecting vessel and recycled, whereas in the drop-on-demand method droplets are produced and printed as required, that is to say droplets are produced only when required for the printing.
- the production of the droplets can be effected, for example, by means of a piezo-inkjet head or by means of thermal energy (bubble jet). Printing by means of a piezo-inkjet head and printing in accordance with the continuous inkjet method are preferred.
- 100 parts of a cotton fabric are introduced at a temperature of 60° C. into a dye bath containing 3.0 parts of the dye of formula (1.1), 3.0 parts of the dye of formula (4.1) and 60 parts of sodium chloride in 1000 parts of water. After 45 minutes at a temperature of 60° C., 20 parts of calcined soda are added. The temperature of the dye bath is maintained at 60° C. for a further 45 minutes. The dyed fabric is then rinsed and dried in the usual manner. A navy-blue dyeing having good fastness properties is obtained.
- Mercerised cotton satin is pad-dyed using a liquor containing 30 g/l of sodium carbonate and 50 g/l of urea (70% liquor pick-up) and dried.
- the print is fully dried and is fixed in saturated steam at 102° C. for 8 minutes, cold-rinsed, washed-off at boiling temperature, rinsed again and dried.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Detergent Compositions (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/711,774 US20100151134A1 (en) | 2004-03-19 | 2010-02-24 | Mixtures of reactive dyes and their use |
| US13/747,575 US8864850B2 (en) | 2004-03-19 | 2013-01-23 | Mixtures of reactive dyes and their use |
| US14/485,841 US9371611B2 (en) | 2004-03-19 | 2014-09-15 | Mixtures of reactive dyes and their use |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04101142 | 2004-03-19 | ||
| EP04101142.0 | 2004-03-19 | ||
| PCT/EP2005/051037 WO2005090485A1 (en) | 2004-03-19 | 2005-03-09 | Mixtures of reactive dyes and their use |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2005/051037 A-371-Of-International WO2005090485A1 (en) | 2004-03-19 | 2005-03-09 | Mixtures of reactive dyes and their use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/711,774 Continuation US20100151134A1 (en) | 2004-03-19 | 2010-02-24 | Mixtures of reactive dyes and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20080244839A1 true US20080244839A1 (en) | 2008-10-09 |
Family
ID=34928914
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10/592,888 Abandoned US20080244839A1 (en) | 2004-03-19 | 2005-03-09 | Mixtures Of Reactive Dyes And Their Use |
| US12/711,774 Abandoned US20100151134A1 (en) | 2004-03-19 | 2010-02-24 | Mixtures of reactive dyes and their use |
| US13/747,575 Expired - Lifetime US8864850B2 (en) | 2004-03-19 | 2013-01-23 | Mixtures of reactive dyes and their use |
| US14/485,841 Expired - Lifetime US9371611B2 (en) | 2004-03-19 | 2014-09-15 | Mixtures of reactive dyes and their use |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/711,774 Abandoned US20100151134A1 (en) | 2004-03-19 | 2010-02-24 | Mixtures of reactive dyes and their use |
| US13/747,575 Expired - Lifetime US8864850B2 (en) | 2004-03-19 | 2013-01-23 | Mixtures of reactive dyes and their use |
| US14/485,841 Expired - Lifetime US9371611B2 (en) | 2004-03-19 | 2014-09-15 | Mixtures of reactive dyes and their use |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US20080244839A1 (de) |
| EP (1) | EP1725618B1 (de) |
| KR (1) | KR101217646B1 (de) |
| CN (1) | CN1934195B (de) |
| AT (1) | ATE517951T1 (de) |
| BR (1) | BRPI0508958B8 (de) |
| MX (1) | MXPA06010605A (de) |
| MY (1) | MY162329A (de) |
| PT (1) | PT1725618E (de) |
| TW (1) | TWI415903B (de) |
| WO (1) | WO2005090485A1 (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7553358B2 (en) * | 2007-05-01 | 2009-06-30 | Canon Kabushiki Kaisha | Ink jet ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus |
| CN101613536B (zh) * | 2008-06-26 | 2013-12-25 | 上海雅运纺织化工股份有限公司 | 藏青色活性染料组合物及其染色应用 |
| CN101817995B (zh) * | 2009-11-16 | 2013-05-08 | 天津德凯化工股份有限公司 | 一种藏青染料 |
| CN101709157B (zh) * | 2009-11-16 | 2013-11-13 | 天津德凯化工股份有限公司 | 一种适用于尼龙染色的活性藏青染料 |
| CN101812244B (zh) * | 2009-11-16 | 2013-06-19 | 天津德凯化工股份有限公司 | 一种用于尼龙染色的活性染料及其制备方法 |
| CN101735658B (zh) * | 2009-11-16 | 2013-08-14 | 天津德凯化工股份有限公司 | 一种适用于尼龙染色的活性藏青染料及其制备方法 |
| BR112013004125A2 (pt) | 2010-08-25 | 2016-06-28 | Huntsman Adv Mat Switzerland | misturas de corantes reativos a fibra e seu uso em um método para tingimento ou impressão tricromática |
| TW201446886A (zh) | 2013-02-19 | 2014-12-16 | Huntsman Adv Mat Switzerland | 反應性染料混合物及其於雙或三色染料或印刷方法中之用途 |
| CN103351645A (zh) * | 2013-07-15 | 2013-10-16 | 湖北华丽染料工业有限公司 | 一种活性蓝染料及其制备方法 |
| CN103540166B (zh) * | 2013-11-01 | 2015-04-08 | 上海雅运纺织化工股份有限公司 | 蓝色活性染料组合物及其在纤维上的染色应用 |
| CN108473785B (zh) * | 2016-01-29 | 2021-02-12 | 亨斯迈先进材料(瑞士)有限公司 | 纤维反应性甲臜染料、其制备及其用途 |
| US10550277B2 (en) | 2016-06-27 | 2020-02-04 | Seiko Epson Corporation | Ink composition, ink set, and recording method |
| JP6897327B2 (ja) * | 2017-05-30 | 2021-06-30 | セイコーエプソン株式会社 | インク組成物、インクセット及び記録方法 |
| EP3336148A1 (de) | 2016-12-15 | 2018-06-20 | DyStar Colours Distribution GmbH | Blaue und marineblaue faserreaktive farbstoffmischungen |
| KR102787946B1 (ko) * | 2020-04-27 | 2025-03-31 | 아크로마 (스위처랜드) 게엠베하 | 반응성 염료들의 혼합물 및 텍스타일 섬유 재료를 염색 또는 프린팅하기 위한 이의 용도 |
| CN114716844A (zh) * | 2022-05-18 | 2022-07-08 | 浙江亿得新材料股份有限公司 | 一种复合高日晒蓝色活性染料及用途 |
| CN118562317A (zh) * | 2024-04-28 | 2024-08-30 | 浙江瑞华化工有限公司 | 一种复合活性蓝染料组合物及其作为活性染料的用途 |
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| US4257770A (en) * | 1978-07-21 | 1981-03-24 | Sumitomo Chemical Company, Limited | Disazo dye composition |
| US5456728A (en) * | 1991-12-04 | 1995-10-10 | Bayer Aktiengesellschaft | Reactive dyestuff mixture having improved properties in combination |
| US5629410A (en) * | 1994-10-13 | 1997-05-13 | Ciba-Geigy Corporation | Reactive azo dyes containing an aminocarbonyl or aminosulfonyl bridge member |
| US5632783A (en) * | 1995-03-03 | 1997-05-27 | Basf Aktiengesellschaft | Mixtures of reactive dyes for navy shades |
| US5704951A (en) * | 1995-03-30 | 1998-01-06 | Hoechst Aktiengesellschaft | Mixtures of blue-dyeing fiber-reactive dyes and their use for dyeing hydroxy-and/or carboxamido-containing fiber material |
| US6126700A (en) * | 1999-01-20 | 2000-10-03 | Everlight Usa, Inc. | Black dye composition |
| US6319291B1 (en) * | 1998-07-21 | 2001-11-20 | Dystar Textilfarben Gmbh & Co. | Navy-blue dye mixture of fiber-reactive azo dyes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4951A (en) * | 1847-02-05 | Manufacture oh hat-bodies | ||
| JP3168624B2 (ja) * | 1991-08-02 | 2001-05-21 | 住友化学工業株式会社 | 反応染料組成物およびそれを用いる繊維材料の染色または捺染方法 |
| DE4237883A1 (de) * | 1992-11-10 | 1994-05-11 | Bayer Ag | Reaktivfarbstoffmischung für Polyester/Cellulosefasermischungen |
| EP0610156B1 (de) * | 1993-02-05 | 1997-05-28 | Ciba SC Holding AG | Verfahren zum Färben oder Bedrucken von cellulosehaltigen Fasermaterialien |
| EP0629667B1 (de) * | 1993-05-18 | 1998-02-25 | Hoechst Aktiengesellschaft | Wasserlöslichse faserreaktive Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP0628606B1 (de) * | 1993-05-18 | 2000-08-23 | DyStar Textilfarben GmbH & Co. Deutschland KG | Triphendioxazinverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbstoffe |
| DE4332047A1 (de) * | 1993-09-21 | 1995-03-23 | Hoechst Ag | Mischungen von faserreaktiven Farbstoffen und deren Verwendung zum Färben von Fasermaterialien |
| JP3405135B2 (ja) * | 1997-06-30 | 2003-05-12 | 住友化学工業株式会社 | 反応染料混合物及びそれを用いる染色又は捺染方法 |
| CH692582A5 (de) * | 1997-09-26 | 2002-08-15 | Bezema Ag | Wasserlösliche Reaktivfarbstoffmischungen und ihre Verwendung zum Färben. |
| GB0208444D0 (en) * | 2002-04-12 | 2002-05-22 | Clariant Int Ltd | Composition for printing recording materials |
| GB0215982D0 (en) * | 2002-07-10 | 2002-08-21 | Dystar Textilfarben Gmbh & Co | Fibre reactive azo dyes |
| MY139986A (en) * | 2005-07-06 | 2009-11-30 | Ciba Sc Holding Ag | Mixtures of reactive dyes and their use |
-
2005
- 2005-03-08 MY MYPI20050945A patent/MY162329A/en unknown
- 2005-03-09 EP EP05716960A patent/EP1725618B1/de not_active Expired - Lifetime
- 2005-03-09 MX MXPA06010605A patent/MXPA06010605A/es active IP Right Grant
- 2005-03-09 AT AT05716960T patent/ATE517951T1/de not_active IP Right Cessation
- 2005-03-09 BR BRPI0508958A patent/BRPI0508958B8/pt not_active IP Right Cessation
- 2005-03-09 WO PCT/EP2005/051037 patent/WO2005090485A1/en not_active Ceased
- 2005-03-09 US US10/592,888 patent/US20080244839A1/en not_active Abandoned
- 2005-03-09 PT PT05716960T patent/PT1725618E/pt unknown
- 2005-03-09 CN CN2005800087343A patent/CN1934195B/zh not_active Expired - Lifetime
- 2005-03-17 TW TW094108118A patent/TWI415903B/zh not_active IP Right Cessation
-
2006
- 2006-10-18 KR KR1020067021590A patent/KR101217646B1/ko not_active Expired - Fee Related
-
2010
- 2010-02-24 US US12/711,774 patent/US20100151134A1/en not_active Abandoned
-
2013
- 2013-01-23 US US13/747,575 patent/US8864850B2/en not_active Expired - Lifetime
-
2014
- 2014-09-15 US US14/485,841 patent/US9371611B2/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4257770A (en) * | 1978-07-21 | 1981-03-24 | Sumitomo Chemical Company, Limited | Disazo dye composition |
| US5456728A (en) * | 1991-12-04 | 1995-10-10 | Bayer Aktiengesellschaft | Reactive dyestuff mixture having improved properties in combination |
| US5629410A (en) * | 1994-10-13 | 1997-05-13 | Ciba-Geigy Corporation | Reactive azo dyes containing an aminocarbonyl or aminosulfonyl bridge member |
| US5632783A (en) * | 1995-03-03 | 1997-05-27 | Basf Aktiengesellschaft | Mixtures of reactive dyes for navy shades |
| US5704951A (en) * | 1995-03-30 | 1998-01-06 | Hoechst Aktiengesellschaft | Mixtures of blue-dyeing fiber-reactive dyes and their use for dyeing hydroxy-and/or carboxamido-containing fiber material |
| US6319291B1 (en) * | 1998-07-21 | 2001-11-20 | Dystar Textilfarben Gmbh & Co. | Navy-blue dye mixture of fiber-reactive azo dyes |
| US6126700A (en) * | 1999-01-20 | 2000-10-03 | Everlight Usa, Inc. | Black dye composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101217646B1 (ko) | 2013-01-02 |
| BRPI0508958B8 (pt) | 2023-05-16 |
| KR20060133030A (ko) | 2006-12-22 |
| BRPI0508958A (pt) | 2007-08-14 |
| MY162329A (en) | 2017-05-31 |
| WO2005090485A1 (en) | 2005-09-29 |
| CN1934195A (zh) | 2007-03-21 |
| US20130133142A1 (en) | 2013-05-30 |
| US20100151134A1 (en) | 2010-06-17 |
| EP1725618A1 (de) | 2006-11-29 |
| ATE517951T1 (de) | 2011-08-15 |
| BRPI0508958B1 (pt) | 2015-07-28 |
| EP1725618B1 (de) | 2011-07-27 |
| PT1725618E (pt) | 2011-09-19 |
| TW200604297A (en) | 2006-02-01 |
| CN1934195B (zh) | 2012-04-25 |
| MXPA06010605A (es) | 2007-04-19 |
| TWI415903B (zh) | 2013-11-21 |
| US8864850B2 (en) | 2014-10-21 |
| US20150000051A1 (en) | 2015-01-01 |
| US9371611B2 (en) | 2016-06-21 |
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