CN1303416A - 单偶氮活性染料 - Google Patents
单偶氮活性染料 Download PDFInfo
- Publication number
- CN1303416A CN1303416A CN99806718A CN99806718A CN1303416A CN 1303416 A CN1303416 A CN 1303416A CN 99806718 A CN99806718 A CN 99806718A CN 99806718 A CN99806718 A CN 99806718A CN 1303416 A CN1303416 A CN 1303416A
- Authority
- CN
- China
- Prior art keywords
- dyestuff
- group
- amino
- phenyl
- formula
- 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.)
- Granted
Links
- 239000000985 reactive dye Substances 0.000 title description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title description 3
- 239000000975 dye Substances 0.000 claims abstract description 95
- 238000004043 dyeing Methods 0.000 claims abstract description 24
- 238000007639 printing Methods 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- -1 Amino Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- YYHJPNVCYHVPJK-UHFFFAOYSA-N naphthalen-1-yl-(2-phenylnaphthalen-1-yl)diazene Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1N=NC1=CC=CC2=CC=CC=C12 YYHJPNVCYHVPJK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002790 naphthalenes Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical compound FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000000976 ink Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 229920000742 Cotton Polymers 0.000 description 25
- 241000675108 Citrus tangerina Species 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000000176 photostabilization Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 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 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 238000004061 bleaching Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229920002678 cellulose Polymers 0.000 description 6
- 235000010980 cellulose Nutrition 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000008234 soft water Substances 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- KKAMNIDZQVXDJV-UHFFFAOYSA-N 7-acetamido-4-hydroxynaphthalene-2-sulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(NC(=O)C)=CC=C21 KKAMNIDZQVXDJV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 2
- 235000011613 Pinus brutia Nutrition 0.000 description 2
- 241000018646 Pinus brutia Species 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- NSSIZMPQSZKECB-UHFFFAOYSA-N (diethoxyamino)oxyethane Chemical compound CCON(OCC)OCC NSSIZMPQSZKECB-UHFFFAOYSA-N 0.000 description 1
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC=N1 ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical class NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- YNJLPAALXOVAPF-UHFFFAOYSA-N OC(O)C(=CO)O Chemical group OC(O)C(=CO)O YNJLPAALXOVAPF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000725 suspension Substances 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
- 230000008719 thickening Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
-
- 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
- C09B62/043—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 containing two or more triazine rings linked together by a non-chromophoric link
-
- 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
- C09B62/085—Monoazo 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
- C09B62/02—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
- C09B62/20—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 pyrimidine ring
- C09B62/24—Azo dyes
- C09B62/245—Monoazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
- D06P1/382—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 reactive group directly attached to heterocyclic group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Abstract
一种如式(Ⅰ)的染料或其盐,其中取代基的定义如权利要求1。这些染料可以用于对含有氮或羟基的有机底物染色或印染并且可以用于制备印刷油墨。
Description
本发明涉及用于纤维材料的染料,特别是苯基-偶氮-萘系列的单偶氮纤维反应性染料和相应的可以用于给纸、棉和类似纺织材料染色的直接染料。
苯基-偶氮-萘系列的纤维反应性染料已为公众所知,这一系列的染料为水溶性的并显示在光、湿度和氧化剂影响下所需的不褪色性,它们适合被用作纤维反应性染料对由毛织品和天然或再生纤维素制成的纺织材料进行染色。
然而为了满足纺织工业的需要,需要改善了不褪色性的特别是耐光性的纤维反应性染料。
令人惊奇地,我们发现了在偶氮部分的苯基上具有特定取代基的苯基-偶氮-萘系列的纤维反应性染料改善了光不褪色性,并且相应的直接染料可以用于对纸张染色。
根据本发明的式(Ⅰ)染料:或其盐,其中磺酸基可以在苯环的3-,4-或5-位,优选在4位,RG键合在萘环的2-或3-位,其结构式为其中X和Y分别选自Cl,F,式-NR4R5的氨基,其中R4和R5分别为氢或被OH、COOH或SO3H或A-SO2-B取代的C1-4烷基,其中A为选自C2-3链烯基、C5-8环烯基或亚苯基的双键基团和B选自-CH=CH2,-CH=CH-Z,-CH2CH2-Z或-CH(CH2Z)-CH2Z,其中Z为可被碱消除的基团,或R4和R5和它们相连的氮原子一起形成含有4到8个碳原子的,另外任选含有选自O,N或S杂原子的杂环,或
优选具有式(Ⅱ)的结构其中X为氯或氟,Y为-NR4R5并且R4和R5和它们相连的氮原子一起形成含有4到8个碳原子的,另外任选含有选自O,N或S杂原子的杂环;或R4为氢或C1-4烷基或R5为C1-4烷基或苯基,它们都可以被羟基、甲基或SO3H取代,或R5为上述定义的-A-SO2-B 。
根据式(Ⅱ)的化合物,特别优选X为氯或氟和Y为定义为β-(β’-(β”-氯代乙基-磺酰基)-乙氧基)-乙基胺,2-甲基苯基氨基,β-磺基乙基氨基,γ-(β’-磺基乙基磺酰基)-丙基氨基,吗啉代,乙基氨基,γ-(β’-硫酸根乙基磺酰基)-丙基氨基,甲基氨基,双N,N-(γ-(β’-硫酸根乙基磺酰基)-丙基)氨基,双N,N-(β-(β’-氯代乙基磺酰基)-乙基)-氨基,N-苯基-N-(β-(β’-硫酸根乙基磺酰基)-乙基)-氨基和N-苯基-N-(γ-(β’-硫酸根乙基磺酰基)-丙基)-氨基的-NR4R5基团。
在式(Ⅱ)中最优选的化合物是X为氟和Y为如吗啉代的-NR4R5基团。根据本发明,另外优选的具体例子为式(Ⅲ)的化合物其中二氟嘧啶连接到萘环的2位。
根据本发明,另外优选的具体例子为式(Ⅳ)的化合物其中X如上述式(Ⅰ)定义,W为双键桥,优选C1-6链烯基或亚苯基。
根据式(Ⅳ)较优选的化合物是X为氯,氟或-NR4R5基团,其中R4和R5分别为氢或任选被OH、COOH或SO3H取代的C1-4烷基;C5-8环烷基;任选被C1-4烷基、SO3H和/或NH2取代的苯基;任选被1到3个SO3H取代的萘基。
根据本发明,用已知的方法将嘧啶或三嗪基团引入到染料或染料前体来形成染料,用Rg为嘧啶或三嗪基,X为例如F、Cl或Br的卤素的Rg-X试剂接触连接到萘环上的氨基的活性氢来完成反应,可以用已知的方法将染料前体转变为新的染料,如用相应于新染料的取代苯基的重氮化胺和染料前体偶合。
当染料含有-NR4R5取代基时,取代基可以早先连接到Rg-X上,与先前提到的氨基的活性氢进行反应,也可以在Rg-X和氨基的活性氢反应后再与Rg连接,在这个例子中,Rg上不稳定的卤素原子和连接于-NHR4R5上N的活性氢进行反应。
通过基团-NH-,将嘧啶或三嗪基团连接于染料或染料前体上,-NH-从含有活性氢的氨基衍生出来,然后固定在染料或染料中间体的萘环上,这种连接可以通过传统化学反应来完成。
上面提到的胺的重氮化反应可以用传统的方法来完成,特别是反应可以在水介质下,在0~10℃的温度条件和pH为0~2的条件下完成。
偶合反应为传统的,可以在水介质中,pH为5~9,优选6~8,温度为10~40℃,优选20~30℃的条件下完成。
这样得到的新染料可以用已知的技术纯化,例如,过滤、洗涤和选择性真空干燥和/或升温干燥。
依赖于合成和纯化方法,可以得到自由或盐形式的新染料。当以盐的形式制备新染料时,不严格要求相关的阳离子,只要相应的盐是水溶性的,可以是应用于传统染料领域的任何非发色团阳离子,这些阳离子的例子有碱金属和未取代或取代的铵离子,例如锂,钠,钾,铵,单、二、三和四甲基铵,三乙基铵和单、二和三乙氧基铵。优选的阳离子为碱金属阳离子和铵离子,最优选钠离子。
根据本发明,新染料的阳离子可以相同或不同,例如可以为上述阳离子的混合物,即染料可以为混和盐的形式。
新染料或它们的混合物可以染色或印染含有羟基或氮的有机底物,优选的底物为皮革和纤维材料,这些材料包括天然或合成的聚酰胺,特别是天然或再生纤维,例如棉、粘胶纤维和人造棉纱。最优选的底物为含棉的纺织材料。
用在染料领域已知的方法来进行染色或印染。在温度范围为30~80℃特别是50~60℃条件下,液体和固体比例为6∶1到30∶1,优选10∶1的条件,优选用浸染的方法来应用活性纤维染料染色。
新的活性纤维染料当作为染料时具有良好的浸染和固染率,而且未固定的混合物易于从底物上洗去。从新纤维反应性染料衍生的染色和印染剂具有良好的耐湿度,例如对洗涤、淡水、海水和汗水的不褪色性,并且特别具有良好的耐光性。它们也可以抗氧化剂,例如含氯的水、含次氯酸盐的漂白剂、过氧化物漂白剂和过硼酸盐洗涤剂。
相应的直接染料可以直接染色或以使用水溶液,例如浓缩的稳定溶液,或四元颗粒和/或上述提到的无机或有机酸盐,来对各种类型的纤维素、棉或皮革染色,特别是纸张或纸张产品。
本染料可以用于漂白和未漂白纸的纸浆染色,它可以根据浸染工艺进一步对纸染色。
用已知的方法进行纸张、皮革或纤维素的染色。
新的染料或它们的产品对于造纸产生的废水的染色实际上没有超出一定的范围,这点对于治理废水非常重要。它们是有接性染料,不会沾污已经染色的纸,并且一般是pH惰性。纸上的染料具有良好的耐光性,长时间曝露在光下,颜色只产生细微的变化。
染色的纸为耐湿的,特别值得一提的是很好的耐醇和肥皂水,另外染色纸的还原剂漂白率特别好。
新染料还可以用于制备特别适合于喷墨打印的印刷油墨。
下面是为了说明本发明的一系列实施例,在这些实施例中所有都是重量或体积份和百分率,除非特殊指出,温度为摄氏温度。
实施例1
在25℃下,将47.8份2-氨基-5-羟基萘-7-磺酸搅拌加入500份水中,通过加入22份30%重量比的氢氧化钠溶解。在30分钟内,向上述溶液中逐滴加入26.8份2,4,6-三氟嘧啶,为了保持混合物的pH值为4~5同时连续加入20%的碳酸钠溶液,反应温度提高到了40~45℃,使用色谱技术来检测反应的终点。将得到的悬浮液冷却到20~25℃,然后倒入在0~5℃,pH为1条件下由34.6份4-氨基苯磺酸和体积50份的4N亚硝酸钠形成的重氮盐溶液中。在偶合的过程中,通过连续加入20%的碳酸钠溶液来保持pH为6~7,用传统的方法、过滤、真空60℃下干燥,盐析出单偶氮化合物。产品结构式如下:
本产品可以将棉染为桔色,着色具有耐光性和耐湿性,并且可以抗氧化剂影响。
实施例2
在0~5℃和pH为1的条件下,将17.3份的3-氨基苯磺酸和25份的4N体积浓度的亚硝酸钠反应得到偶氮盐,再将28.1份2-乙酰基氨基-5-羟基萘-7-磺酸溶于200份水中与其混和,在偶合的过程中,为了保持混合物的pH值为7~8连续加入20%的碳酸钠溶液。反应结束后,抽滤干燥产品,将经抽滤后仍然湿的残留物溶于300份4%重量比的氢氧化钠溶液中,并将反应溶液加热到90~100℃,直到通过薄层色谱检测,乙酰基的皂化已经完成,将具有以下结构的化合物溶液冷却到20℃,通过加入30%的盐酸调整pH值为5~6。在此pH条件下,在30分钟内,将16.1份2,4,6-三氟吡啶逐滴加入,为了保持混合物的pH值连续加入20%的碳酸钠溶液,并且保持反应温度为40~45℃,当反应结束后,通过过滤、真空60℃下干燥,盐析出染料,染料结构式如下:
本产品可以将棉染为桔色,染色和印染着色具有耐光性和耐湿性,并且对氧化剂稳定。
实施例3~11
表1列出了一些染料,它们用相应的起始物质根据实施例1和2的类似方法制备。这些例子中的染料可将棉染色或印染为桔色或红色,并具有良好的耐光性和耐湿性,而且对氧化剂稳定。
实施例12
根据EP-A-0172790描述的方法,将142份2,4,6-三氟三嗪加入到根据实施例制备得到的437份化合物1的10000份冰水溶液中,在0~5℃下,大约30分钟后,将87份吗啉加入到溶液中,然后先在0~5℃下,再在10~15℃下搅拌4~5小时,为了保持混合物的pH值为6~7连续加入20%的碳酸钠溶液,然后加入100份的KCl,沉淀出染料,接着过滤并在真空50℃下干燥,得到的染料具有结构
本产品可以将棉染为桔色,染色和印染着色具有耐光性和耐湿性,并且对氧化剂稳定。
实施例13~37
表2和3列出了一些染料,它们用相应的起始物质根据实施例12的类似方法制备。这些例子中的染料可将棉染色或印染为桔色或红色,并具有良好的耐光性和耐湿性,而且对氧化剂稳定。
实施例38
在0~5℃和pH为1的条件下,将173份的4-氨基苯磺酸和250份的体积摩尔浓度4N亚硝酸钠反应得到偶氮盐,再将281份2-乙酰基氨基-5-羟基萘-7-磺酸溶于2000份水中与其混和,在偶合的过程中,为了保持混合物的pH值为7~8连续加入20%的碳酸钠溶液。反应结束后,抽滤干燥产品,将经抽滤后仍然湿的残留物溶于3000份4%重量比的氢氧化钠溶液中,并将反应溶液加热到90~100℃,直到通过薄层色谱检测,乙酰基的皂化已经完成,反应结束后,将以下结构的化合物抽滤干燥,在30分钟内,将抽滤后仍然湿润的残留物在45℃的2500份水和含有405份2,4-二氯-6-(6’8’-二磺基萘基-2-)氨基三嗪的2000份悬浮水溶液的混和溶液中溶解,其中温度保持在40~45℃,pH值保持在为7~7.5。缩合反应结束后,用已知的方法盐析出下式的染料同时冷却,抽提过滤和在50℃,真空干燥。本染料可以将棉染为桔色,染色和印染着色具有耐光性和耐湿性,并且对氧化剂稳定。
实施例39
边搅拌边将84份实施例38得到的染料加入到800份水和43份二乙基胺的混和液中,接着将混合物加热到80~90℃,并保持温度不变直到反应结束。一直搅拌染料溶液直到溶液冷却和染料盐析出来,再过滤和在60℃真空干燥,得到的染料具有下式可以将纤维素纤维特别是纸张染成桔色,它的耐湿和耐光性良好。
实施例40~70
表4和5公开了一些用实施例38~39的类似方法得到的染料,在这些物质可以将纸张染为桔色或红色,并具有良好的耐光性和耐湿性。
应用实施例A
将0.3份实施例1染料溶于100份软水中,并加入8份Gluber盐(煅烧过的),将染浴加热到50℃,然后加入10份棉织物(漂白过的),保持50℃温度,加入碳酸钠,接着加热染浴到60℃,在60℃下再染色1小时,用冷流水漂洗染色的织物3分钟,用热水再浸洗3分钟。用含有0.25份Marseille肥皂的500份沸腾软水洗涤染料15分钟,用热流水漂洗(3分钟)并离心,在约70℃的干燥箱中干燥,染色的桔色棉显示了良好的不褪色性,特别是耐光性和湿性,并且对氧化剂稳定。
应用实施例B
向100份软水和5份Gluber盐(煅烧过的)的染浴中加入10份棉织物(漂白过的),在10分钟内加热到50℃,并加入0.5份实施例1染料,在50℃下进行30分钟后,加入1份碳酸钠(煅烧过的),再加热染浴到60℃,并在60℃下继续染色45分钟,根据应用实施例A的方法漂洗染色的织物,先用冷流水,再用热水,然后用沸水洗涤,在漂洗和干燥后,染色的桔色棉具有和应用实施例A相同的不褪色性。
类似地,用应用实施例A或B的方法,实施例2~37的染料或其染料混合物可以用于给棉染色,棉的着色为桔色或红色,并具有良好的不褪色性,特别是耐光性。
应用实施例C
印染浆包括
40 份实施例1染料
100 份尿素
350 份水
500 份4%的藻酸钠增稠剂和
10 份碳酸氢钠
1000份
根据传统的印染方法,将整个1000份应用于棉织品,将印染的棉织品干燥,并在102~104℃的蒸汽中固色4~8分钟,接着在冷水中,然后在热水中漂洗,接着沸水中洗涤(根据应用实施例A的方法)并干燥,桔色的印染一般具有良好的不褪色性。
类似地,根据应用实施例C的方法,实施例2到37的染料或染料混合物可以印染棉,得到的桔色或红色印染具有良好的不褪色性,特别是良好的耐光性。
应用实施例D
将70份化学漂白过的亚硫酸松木纤维素和30份漂白过的桦木亚硫酸纤维素在2000份水的Hollander中研磨,再将0.2份实施例38的染料洒入这一纸浆中,混和20分钟后,制造出纸张,用这种方法得到的吸水纸被染为桔色,废水为无色。
应用实施例E
将0.5份实施例38染料粉末溶于100份热水中,并冷却到室温,加入100份化学漂白过的在Hollander中和200份水研磨过的亚硫酸纤维素到溶液中,混和15分钟后,用松香胶料和硫酸铝作为胶料,这样得到的纸为桔色,并且废水易处理,具有良好的耐湿性和耐光性。
应用实施例F
在40~50℃,通过显示组合物的染料来检测未上胶纸的吸收范围:
0.5份实施例38染料
0.5份淀粉
99.0份水
用两个滚子挤压掉多余的染料,纸干燥的范围为桔色。
用实施例D到F的方法,使用实施例39到70的染料或相应的染料制剂来染色,纸的着色为桔色或红色并且具有高不褪色性。
应用实施例G
将50份亚硫酸松木纤维素和50份经漂白的纤维素[搅拌度30°SR(°SR=Schopper Riegler度)与5份实施例38中染料的pH=4,硬度为10°dH的水中混合。16分钟后形成薄片,纸被染成深橙色。相反的,在pH=7下进行的染色显示不出色泽与深度的变化。
应用实施例H
在60℃,将1.1份实施例38染料溶液100份软水中,接着用900份冷的软水稀释,然后将100份棉针织物(漂白过)加入到染浴中,5分钟后,加入10份煅烧后的硫酸钠和2份硫酸铵,在70分钟内,染浴的温度的继续升高到98℃,保持这一温度20分钟,然后经过30分钟冷却到70℃,首先将染色的物质在冷软水中漂洗2分钟,然后再用自来水漂洗2分钟,离心并干燥,棉着桔色。
应用实施例I
在25℃,在100份自来水中,不立即染色,将以类似实施例H的方法,以1/1标准色染深度,用实施例38染料染色的100份棉针织物和5份氯化钠混和,并和经二乙基三胺和双氰胺反应处理得到的4份试剂混和,染浴的pH值设为6.5~7,在20分钟内,将染浴加热到60℃,并保持此温度20分钟,然后用冷自来水漂洗,这样处理过的着桔色的棉具有优良的耐洗性和良好的耐光性。
应用实施例J
将以类似实施例H的方法,以1/1标准色染深度,用实施例38染料染色的棉在轧染机上充满下述溶液,此溶液含有通过实施例I处理后试剂和二羟甲基二羟基乙烯基脲反应得到的100g/l处理后试剂并含有淬水催化剂,接着挤压到浓度为80%,然后在175~180℃下,在展幅机上振动干燥45秒。很明显着桔色的棉具有良好的耐洗性,同时在不褪色性上有惊人的提高,并降低了纤维素纤维的膨胀值。
应用实施例K
在25℃下,边搅拌边将实施例38得到的2.5份染料溶于20份二甘醇和77.5份水中,得到适合于喷墨打印的打印墨。
Claims (12)
1、式(Ⅰ)的染料根据本发明的式(Ⅰ)染料或其盐,其中磺酸基可以在苯环的3-或4-或5位,优选在4位,RG键合在萘环的2-或3-位,其结构式为其中X和Y分别独立地为选自Cl,F,式-NR4R5的氨基,其中R4和R5独立为氢或被OH、COOH或SO3H或A-SO2-B取代的C1-4烷基,其中A为选自C2-3链烯基、C5-8环烯基或亚苯基的双键基团和B选自-CH=CH2,-CH=CH-Z,-CH2CH2-Z或-CH(CH2Z)-CH2Z,其中Z为可被碱消除的基团,或R4和R5和它们相连的氮原子一起形成含有4到8个碳原子的,另外任选含有选自O,N或S杂原子的杂环,或
3、根据权利要求2的染料,其中X为氯或氟和Y为定义为β-(β’-(β”-氯代乙基-磺酰基)-乙氧基)-乙基胺,2-甲基苯基氨基,β-磺基乙基氨基,γ-(β’-磺基乙基磺酰基)-丙基氨基,吗啉代,乙基氨基,γ-(β’-硫酸根乙基磺酰基)-丙基氨基,甲基氨基,双N,N-(γ-(β’-硫酸根乙基磺酰基)-丙基)氨基,双N,N-(β-(β’-氯代乙基磺酰基)-乙基)-氨基,N-苯基-N-(β-(β’-硫酸根乙基磺酰基)-乙基)-氨基和N-苯基-N-(γ-(β’-硫酸根乙基磺酰基)-丙基)-氨基的-NR4R5基团。
4、根据权利要求2的染料,其中X为氯和Y具有权利要求3的定义。
5、根据权利要求3的染料,其中Y为吗啉代的-NR4R5基团。
8、根据权利要求7的染料,其中W为C1-6链烯基或亚苯基。
9、根据权利要求7的染料,其中X为氯,氟或-NR4R5基团,其中R4和R5分别为氢或任选被OH、COOH或SO3H取代的C1-4烷基;C5-8环烷基;任选被C1-4烷基、SO3H和/或NH2取代的苯基;任选被1到3个SO3H取代的萘基。
10、制备前述权利要求定义的染料的方法,包括将具有活性氨基氢原子的苯基-偶氮-萘系列染料与Rg-X试剂反应,其中Rg为含有不稳定卤的嘧啶或三嗪基,X为选自F、Cl或Br的卤素。
11、对含有羟基或氮有机底物染色或印染的方法,包括应用权利要求1的染料。
12、制备印刷油墨的方法,包括使用权利要求1染料。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9811548.8A GB9811548D0 (en) | 1998-05-30 | 1998-05-30 | New monoazo dyestuffs |
GB9811548.8 | 1998-05-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1303416A true CN1303416A (zh) | 2001-07-11 |
CN1101427C CN1101427C (zh) | 2003-02-12 |
Family
ID=10832894
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN99806718A Expired - Fee Related CN1101427C (zh) | 1998-05-30 | 1999-05-26 | 单偶氮活性染料 |
Country Status (16)
Country | Link |
---|---|
US (1) | US6127531A (zh) |
EP (1) | EP1084196B1 (zh) |
JP (1) | JP4545931B2 (zh) |
KR (1) | KR100606394B1 (zh) |
CN (1) | CN1101427C (zh) |
BR (1) | BR9910840B1 (zh) |
DE (1) | DE69934115T2 (zh) |
ES (1) | ES2276517T3 (zh) |
GB (1) | GB9811548D0 (zh) |
HK (1) | HK1038372A1 (zh) |
ID (1) | ID27195A (zh) |
PT (1) | PT1084196E (zh) |
TR (1) | TR200003520T2 (zh) |
TW (1) | TW568941B (zh) |
WO (1) | WO1999063005A1 (zh) |
ZA (1) | ZA200006610B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1954035B (zh) * | 2004-05-19 | 2010-12-29 | 克莱里安特财务(Bvi)有限公司 | 单偶氮染料 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003528965A (ja) * | 2000-03-28 | 2003-09-30 | クラリアント インターナショナル リミティド | 記録材料の印刷のための組成物 |
GB0113307D0 (en) * | 2001-06-01 | 2001-07-25 | Clariant Int Ltd | Organic compounds |
GB0124842D0 (en) * | 2001-10-17 | 2001-12-05 | Clariant Int Ltd | Improvements relating to organic compounds |
WO2003052006A1 (en) | 2001-12-19 | 2003-06-26 | Clariant International Ltd | Acidic mono azo dyestuffs |
BR0309782B1 (pt) * | 2002-04-27 | 2015-01-06 | Dystar Colours Distrib Gmbh | Corante reativo com fibra solúvel em água e processo para preparação de corantre |
DE10316402A1 (de) * | 2003-04-10 | 2004-10-21 | Clariant Gmbh | Methansulfonamid-Azofarbstoffe |
US8935381B2 (en) * | 2007-11-27 | 2015-01-13 | Zettics, Inc. | Method and apparatus for real-time collection of information about application level activity and other user information on a mobile data network |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3332212A1 (de) * | 1982-09-17 | 1984-03-22 | Sandoz-Patent-GmbH, 7850 Lörrach | Reaktive monoazoverbindungen |
JPS6086169A (ja) * | 1983-10-19 | 1985-05-15 | Nippon Kayaku Co Ltd | アゾ化合物の製法 |
JPS60208366A (ja) * | 1984-04-02 | 1985-10-19 | Sumitomo Chem Co Ltd | トリアジン化合物およびそれを用いる繊維材料の染色または捺染法 |
US4686286A (en) * | 1984-06-06 | 1987-08-11 | Mitsubishi Chemical Industries Limited | Disazo reactive dyestuffs for cellulose fibers |
JPH0619046B2 (ja) * | 1985-12-06 | 1994-03-16 | 三菱化成株式会社 | ジスアゾ化合物およびそれを含有する染料組成物 |
EP0426618A1 (de) * | 1989-11-01 | 1991-05-08 | Ciba-Geigy Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
EP0584045B1 (de) * | 1992-08-19 | 2000-03-01 | Ciba SC Holding AG | Faserreaktive Farbstoffe, deren Herstellung und Verwendung |
CH685762A5 (de) * | 1992-09-17 | 1995-09-29 | Sandoz Ag | Faserreaktive Monoazofarbstoffe. |
GB9306452D0 (en) * | 1993-03-29 | 1993-05-19 | Zeneca Ltd | Organic compounds |
MY116477A (en) * | 1993-05-17 | 2004-02-28 | Ciba Sc Holding Ag | Reactive dyes, processes for their preparation and their use |
TW293029B (zh) * | 1993-05-17 | 1996-12-11 | Ciba Geigy Ag | |
DE4332047A1 (de) * | 1993-09-21 | 1995-03-23 | Hoechst Ag | Mischungen von faserreaktiven Farbstoffen und deren Verwendung zum Färben von Fasermaterialien |
JP3115187B2 (ja) * | 1993-09-29 | 2000-12-04 | ダイスタージャパン株式会社 | 水溶性染料混合物及びセルロース繊維材料の染色又は捺染法 |
DE4338117A1 (de) * | 1993-11-08 | 1995-05-11 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
CN1173888A (zh) * | 1995-02-07 | 1998-02-18 | 拜尔公司 | 活性偶氮染料的制备方法 |
ES2164320T3 (es) * | 1996-09-26 | 2002-02-16 | Ciba Sc Holding Ag | Mezclas de colorantes, procedimiento para su obtencion y utilizacion de las mismas. |
-
1998
- 1998-05-30 GB GBGB9811548.8A patent/GB9811548D0/en not_active Ceased
-
1999
- 1999-05-26 DE DE69934115T patent/DE69934115T2/de not_active Expired - Lifetime
- 1999-05-26 WO PCT/IB1999/000951 patent/WO1999063005A1/en active IP Right Grant
- 1999-05-26 JP JP2000552205A patent/JP4545931B2/ja not_active Expired - Fee Related
- 1999-05-26 ES ES99919492T patent/ES2276517T3/es not_active Expired - Lifetime
- 1999-05-26 BR BRPI9910840-2A patent/BR9910840B1/pt not_active IP Right Cessation
- 1999-05-26 KR KR1020007013407A patent/KR100606394B1/ko not_active IP Right Cessation
- 1999-05-26 PT PT99919492T patent/PT1084196E/pt unknown
- 1999-05-26 TR TR2000/03520T patent/TR200003520T2/xx unknown
- 1999-05-26 ID IDW20002476A patent/ID27195A/id unknown
- 1999-05-26 CN CN99806718A patent/CN1101427C/zh not_active Expired - Fee Related
- 1999-05-26 EP EP99919492A patent/EP1084196B1/en not_active Expired - Lifetime
- 1999-05-26 US US09/320,231 patent/US6127531A/en not_active Expired - Lifetime
- 1999-05-28 TW TW088108867A patent/TW568941B/zh not_active IP Right Cessation
-
2000
- 2000-11-14 ZA ZA200006610A patent/ZA200006610B/en unknown
-
2001
- 2001-12-28 HK HK01109178A patent/HK1038372A1/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1954035B (zh) * | 2004-05-19 | 2010-12-29 | 克莱里安特财务(Bvi)有限公司 | 单偶氮染料 |
Also Published As
Publication number | Publication date |
---|---|
JP2002517539A (ja) | 2002-06-18 |
DE69934115T2 (de) | 2007-03-15 |
WO1999063005A1 (en) | 1999-12-09 |
CN1101427C (zh) | 2003-02-12 |
EP1084196A1 (en) | 2001-03-21 |
US6127531A (en) | 2000-10-03 |
GB9811548D0 (en) | 1998-07-29 |
JP4545931B2 (ja) | 2010-09-15 |
ZA200006610B (en) | 2001-11-14 |
BR9910840A (pt) | 2001-02-20 |
BR9910840B1 (pt) | 2010-09-08 |
KR20010043900A (ko) | 2001-05-25 |
ES2276517T3 (es) | 2007-06-16 |
ID27195A (id) | 2001-03-08 |
EP1084196B1 (en) | 2006-11-22 |
TW568941B (en) | 2004-01-01 |
HK1038372A1 (en) | 2002-03-15 |
KR100606394B1 (ko) | 2006-07-28 |
PT1084196E (pt) | 2007-01-31 |
TR200003520T2 (tr) | 2001-06-21 |
DE69934115D1 (de) | 2007-01-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1054868C (zh) | 活性染料及其制备方法和用途 | |
DE2557141C2 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
CN1118520C (zh) | 用于对有机基质进行染色的三苯基二䓬嗪染料 | |
JPH02292370A (ja) | アニオン性ジオキサジン化合物 | |
CN1160421C (zh) | 染料混合物和它的制备方法及其应用 | |
CN1090655C (zh) | 染料 | |
CN1101427C (zh) | 单偶氮活性染料 | |
JPS62292860A (ja) | トリアジニル基含有モノアゾ化合物 | |
CN1418243A (zh) | 纤维反应性双偶氮化合物 | |
US5149791A (en) | Chlorotriazine reactive dyes having a 4-methoxy-2-sulfoaniline diazo component and 2-amino-5-naphthol-7-sulfonic acid coupling component | |
CN1160420C (zh) | 纤维活性偶氮染料的混合物及其应用 | |
CN100387657C (zh) | 二重氮化合物的用途 | |
CH624139A5 (zh) | ||
CN1149265C (zh) | 新的双偶氮染料 | |
JP4138877B2 (ja) | 繊維反応性染料 | |
EP1514905B1 (en) | High light fastness reactive red dyes | |
CN1235980C (zh) | 水溶性纤维用活性染料及其制备方法和用途 | |
CN1425045A (zh) | 包括水溶性纤维反应性偶氮染料的染料混合物,它们的制备方法和用途 | |
KR0181491B1 (ko) | 반응성 염료 및 이의 염료제제 | |
CN1496389A (zh) | 对纤维具有活性的单偶氮染料的铜络合物 | |
US5371200A (en) | Fibre-reactive formazan dyes, processes for their preparation and their use | |
CN1289610C (zh) | 新的甲活性染料 | |
CN1056634C (zh) | 二重氮化合物及它的制备方法和其在染色或印染中的应用 | |
CN1209419C (zh) | 甲化合物及使用甲化合物染色的方法 | |
CN1135506A (zh) | 蒽醌活性染料及其印染方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20030212 Termination date: 20150526 |
|
EXPY | Termination of patent right or utility model |