CN1097076C - 活性染料、它们的制备及用途 - Google Patents
活性染料、它们的制备及用途 Download PDFInfo
- Publication number
- CN1097076C CN1097076C CN97102273A CN97102273A CN1097076C CN 1097076 C CN1097076 C CN 1097076C CN 97102273 A CN97102273 A CN 97102273A CN 97102273 A CN97102273 A CN 97102273A CN 1097076 C CN1097076 C CN 1097076C
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- CN
- China
- Prior art keywords
- group
- formula
- amino
- ethyl
- compound
- 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.)
- Expired - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 238000004043 dyeing Methods 0.000 claims abstract description 28
- -1 1-pyridyl Chemical group 0.000 claims description 74
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000005987 sulfurization reaction Methods 0.000 claims 1
- 238000007639 printing Methods 0.000 abstract description 8
- 239000000985 reactive dye Substances 0.000 abstract description 5
- 239000002657 fibrous material Substances 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000004744 fabric Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- 239000003599 detergent Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002932 luster Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- PPSSQRUPSRPZON-UHFFFAOYSA-N nitrobenzene;sodium Chemical compound [Na].[O-][N+](=O)C1=CC=CC=C1 PPSSQRUPSRPZON-UHFFFAOYSA-N 0.000 description 3
- 238000009980 pad dyeing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003863 ammonium salts Chemical group 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical group NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 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 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/01—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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4415—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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/24—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with formation of —O—SO2—R or —O—SO3H radicals
-
- 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo 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
- D06P1/02—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 azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH150/96 | 1996-01-19 | ||
| CH15096 | 1996-01-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1163291A CN1163291A (zh) | 1997-10-29 |
| CN1097076C true CN1097076C (zh) | 2002-12-25 |
Family
ID=4180395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97102273A Expired - Lifetime CN1097076C (zh) | 1996-01-19 | 1997-01-17 | 活性染料、它们的制备及用途 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5817779A (enExample) |
| EP (1) | EP0785237B1 (enExample) |
| JP (1) | JP4171081B2 (enExample) |
| KR (1) | KR100433351B1 (enExample) |
| CN (1) | CN1097076C (enExample) |
| DE (1) | DE59703980D1 (enExample) |
| ES (1) | ES2159826T3 (enExample) |
| ID (1) | ID15914A (enExample) |
| MY (1) | MY117759A (enExample) |
| PT (1) | PT785237E (enExample) |
| SG (1) | SG79212A1 (enExample) |
| TW (1) | TW454030B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104968732A (zh) * | 2012-06-18 | 2015-10-07 | 德司达染料分销有限公司 | 不含金属的活性染料,及其制备方法和应用 |
| CN105176139A (zh) * | 2015-05-26 | 2015-12-23 | 浙江龙盛集团股份有限公司 | 一种多偶氮棕色活性染料化合物及其制备方法和应用 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG68660A1 (en) * | 1997-04-07 | 1999-11-16 | Ciba Sc Holding Ag | Mixtures of reactive dyes and their use |
| US5989298A (en) * | 1997-04-07 | 1999-11-23 | Ciba Speciality Chemicals Corporation | Mixtures of reactive dyes and their use |
| DE69903599T2 (de) | 1998-07-21 | 2003-06-12 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Marineblaue Mischungen von faserreaktiven Azofarbstoffen |
| ATE316990T1 (de) * | 2001-10-12 | 2006-02-15 | Ciba Sc Holding Ag | Faserreaktive azofarbstoffe, deren herstellung und deren verwendung |
| WO2003040239A1 (en) * | 2001-11-07 | 2003-05-15 | Ciba Specialty Chemicals Holding Inc. | Fibre-reactive dyes, their preparation and their use |
| DE10212771A1 (de) * | 2002-03-22 | 2003-10-02 | Dystar Textilfarben Gmbh & Co | Wasserlösliche Mono- und Disazofarbstoffe |
| CN1918245B (zh) * | 2004-02-13 | 2010-11-03 | 西巴特殊化学品控股有限公司 | 活性染料混合物及其用途 |
| CN1317336C (zh) * | 2004-09-16 | 2007-05-23 | 明德国际仓储贸易(上海)有限公司 | 季铵盐双偶氮反应性染料及其应用 |
| CN1847324A (zh) * | 2005-04-13 | 2006-10-18 | 明德国际仓储贸易(上海)有限公司 | 纤维反应性染料 |
| CH695613A5 (de) * | 2005-06-08 | 2006-07-14 | Bezema Ag | Mischungen von schwermetallfreien faserreaktiven Farbstoffen auf der Basis von Triazo-Verbindungen, deren Herstellung und Verwendung. |
| DE102005047391A1 (de) | 2005-10-05 | 2007-04-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Farbstoffe und Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
| DE102006028229A1 (de) * | 2006-06-20 | 2008-01-10 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
| DE102007005795A1 (de) | 2007-02-06 | 2008-08-07 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Mischungen von faserreaktiven Azofarbstoffen |
| CN101235216B (zh) * | 2008-01-22 | 2010-07-21 | 天津德凯化工股份有限公司 | 一种橙色活性染料及其制备方法 |
| US8349029B2 (en) | 2008-12-09 | 2013-01-08 | Dystar Colours Deutschland Gmbh | Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof |
| DE102008054404A1 (de) | 2008-12-09 | 2010-06-10 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Faserreaktive Azofarbstoffe und Farbstoffmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CN103703083A (zh) | 2011-08-04 | 2014-04-02 | 亨斯迈先进材料（瑞士）有限公司 | 活性染料的混合物及其用途 |
| CN102329522B (zh) * | 2011-09-29 | 2016-08-03 | 天津德凯化工股份有限公司 | 一种活性染料及其制备方法 |
| CN104119692A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种活性橙染料化合物及其应用 |
| CN104119693A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种橙色活性染料化合物及其应用 |
| CN104119694A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种活性橙染料化合物及应用 |
| EP2862902A1 (en) * | 2013-08-29 | 2015-04-22 | DyStar Colours Distribution GmbH | Dye mixtures of metal free reactive dyes, production and use |
| ES2901929T3 (es) * | 2018-02-16 | 2022-03-24 | Huntsman Adv Mat Switzerland | Procedimiento para la curtición y tinción simultáneas de material fibroso que contiene colágeno |
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- 1997-01-06 MY MYPI97000036A patent/MY117759A/en unknown
- 1997-01-10 PT PT97810011T patent/PT785237E/pt unknown
- 1997-01-10 EP EP97810011A patent/EP0785237B1/de not_active Expired - Lifetime
- 1997-01-10 DE DE59703980T patent/DE59703980D1/de not_active Expired - Lifetime
- 1997-01-10 ES ES97810011T patent/ES2159826T3/es not_active Expired - Lifetime
- 1997-01-14 JP JP00436397A patent/JP4171081B2/ja not_active Expired - Fee Related
- 1997-01-14 TW TW086100314A patent/TW454030B/zh not_active IP Right Cessation
- 1997-01-15 US US08/783,183 patent/US5817779A/en not_active Expired - Lifetime
- 1997-01-15 SG SG9700090A patent/SG79212A1/en unknown
- 1997-01-17 ID IDP970130A patent/ID15914A/id unknown
- 1997-01-17 CN CN97102273A patent/CN1097076C/zh not_active Expired - Lifetime
- 1997-01-17 KR KR1019970001207A patent/KR100433351B1/ko not_active Ceased
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| EP0647683A1 (de) * | 1993-10-07 | 1995-04-12 | Ciba-Geigy Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104968732A (zh) * | 2012-06-18 | 2015-10-07 | 德司达染料分销有限公司 | 不含金属的活性染料,及其制备方法和应用 |
| CN104968732B (zh) * | 2012-06-18 | 2017-08-08 | 德司达染料分销有限公司 | 不含金属的活性染料，及其制备方法和应用 |
| CN105176139A (zh) * | 2015-05-26 | 2015-12-23 | 浙江龙盛集团股份有限公司 | 一种多偶氮棕色活性染料化合物及其制备方法和应用 |
| CN105176139B (zh) * | 2015-05-26 | 2020-09-29 | 浙江龙盛集团股份有限公司 | 一种多偶氮棕色活性染料化合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09194749A (ja) | 1997-07-29 |
| ID15914A (id) | 1997-08-21 |
| EP0785237B1 (de) | 2001-07-11 |
| JP4171081B2 (ja) | 2008-10-22 |
| CN1163291A (zh) | 1997-10-29 |
| ES2159826T3 (es) | 2001-10-16 |
| KR100433351B1 (ko) | 2005-09-12 |
| EP0785237A1 (de) | 1997-07-23 |
| TW454030B (en) | 2001-09-11 |
| PT785237E (pt) | 2001-12-28 |
| MY117759A (en) | 2004-08-30 |
| US5817779A (en) | 1998-10-06 |
| DE59703980D1 (de) | 2001-08-16 |
| KR970059234A (ko) | 1997-08-12 |
| SG79212A1 (en) | 2001-03-20 |
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