TW593559B - Compounds of monoazo dyes and process for preparing the same - Google Patents
Compounds of monoazo dyes and process for preparing the same Download PDFInfo
- Publication number
- TW593559B TW593559B TW090124932A TW90124932A TW593559B TW 593559 B TW593559 B TW 593559B TW 090124932 A TW090124932 A TW 090124932A TW 90124932 A TW90124932 A TW 90124932A TW 593559 B TW593559 B TW 593559B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- scope
- group
- patent application
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 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 title claims description 5
- 239000000975 dye Substances 0.000 title abstract description 28
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000758 substrate Substances 0.000 claims abstract description 10
- 238000007641 inkjet printing Methods 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 238000004043 dyeing Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 238000007639 printing Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- -1 formula (I) Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000010866 blackwater Substances 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000470 constituent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229920000742 Cotton Polymers 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 239000004744 fabric Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- 239000001047 purple dye Substances 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000009300 Ehretia acuminata Nutrition 0.000 description 1
- 244000046038 Ehretia acuminata Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 241000084978 Rena Species 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-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 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
- WBHQBSYUUJJSRZ-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [H+].[H+].[Na+].[O-]S([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940098465 tincture Drugs 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/04—Azo compounds in general
- C09B45/08—Copper compounds
-
- 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
-
- 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
- C09B62/095—Metal complex azo 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
- C09B62/255—Metal complex azo 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
- C09B62/4416—Metal complex azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH19932000 | 2000-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW593559B true TW593559B (en) | 2004-06-21 |
Family
ID=4567042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090124932A TW593559B (en) | 2000-10-10 | 2001-10-09 | Compounds of monoazo dyes and process for preparing the same |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6974497B2 (enExample) |
| EP (1) | EP1332181B1 (enExample) |
| JP (1) | JP2004511610A (enExample) |
| KR (1) | KR100814209B1 (enExample) |
| CN (1) | CN1325573C (enExample) |
| AT (1) | ATE443108T1 (enExample) |
| BR (1) | BR0114476B1 (enExample) |
| DE (1) | DE60139949D1 (enExample) |
| ES (1) | ES2329876T3 (enExample) |
| MX (1) | MXPA03002684A (enExample) |
| PT (1) | PT1332181E (enExample) |
| TW (1) | TW593559B (enExample) |
| WO (1) | WO2002031057A2 (enExample) |
| ZA (1) | ZA200301716B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100455567B1 (ko) * | 2002-05-03 | 2004-11-06 | (주)경인양행 | 수용성 섬유-반응성 염료 |
| KR100510242B1 (ko) * | 2002-11-22 | 2005-08-26 | (주)경인양행 | 신규의 반응성 회색 염료 및 그것의 제조방법 |
| DE102008026584A1 (de) * | 2008-06-03 | 2009-12-10 | Clariant International Limited | Verbessertes Cyanfarbmittel |
| WO2013047386A1 (ja) | 2011-09-30 | 2013-04-04 | 富士フイルム株式会社 | 捺染用水性着色組成物、捺染方法、及び布帛 |
| CN103709784A (zh) * | 2013-12-09 | 2014-04-09 | 浙江劲光化工有限公司 | 一种印花用蓝色活性染料及其制备方法 |
| CN106854382A (zh) * | 2017-01-03 | 2017-06-16 | 上海安诺其集团股份有限公司 | 一种偶氮类化合物及其应用 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE571942A (enExample) * | 1957-10-11 | |||
| DE1644366B1 (de) * | 1957-11-29 | 1971-07-29 | Sandoz Ag | Verfahren zur Herstellung von metallhaltigen wasserloeslichen Pyrimidinreaktiv-Azofarbstoffen |
| CH425039A (de) * | 1959-12-04 | 1966-11-30 | Geigy Ag J R | Verfahren zur Herstellung von metallhaltigen reaktiven Azofarbstoffen |
| US3502642A (en) * | 1967-07-24 | 1970-03-24 | Geigy Ag J R | Reactive copper-containing benzeneazonaphthalene dyes containing a trichloropyrimidine group |
| GB2031931B (en) | 1978-09-12 | 1982-11-10 | Bayer Ag | Disazo dyestuffs |
| DE2839562A1 (de) * | 1978-09-12 | 1980-03-27 | Bayer Ag | Faserreaktive azofarbstoffe |
| EP0172790B1 (de) | 1984-08-21 | 1992-07-29 | Ciba-Geigy Ag | Verfahren zur kontinuierlichen Umsetzung von Cyanurfluorid mit Aminonaphtholsulfonsäuren |
| EP0265747B1 (de) * | 1986-10-29 | 1992-04-01 | C. Rob. Hammerstein GmbH | Fahrzeugsitz mit einer Längsführung, mit einer Höhen- oder Neigungsverstellung und mit einer Gurtschlossbefestigung |
| DE3835724A1 (de) * | 1988-10-20 | 1990-04-26 | Sandoz Ag | Faserreaktive metallisierte monoazoverbindungen |
| ES2075071T3 (es) * | 1988-10-20 | 1995-10-01 | Sandoz Ag | Colorantes azoicos reactivos con fibras. |
| EP0499588A1 (de) * | 1991-02-15 | 1992-08-19 | Ciba-Geigy Ag | Reaktivefarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| DE4125754A1 (de) | 1991-08-03 | 1993-02-04 | Bayer Ag | Fluorpyrimidin-reaktivfarbstoffe |
| GB2270923B (en) * | 1992-09-24 | 1995-11-08 | Sandoz Ltd | Fibre-reactive monoazo copper complexes |
| JP3657627B2 (ja) * | 1992-10-12 | 2005-06-08 | クラリアント ファイナンス （ビーブイアイ） リミティド | 繊維反応性アゾ染料化合物およびその製造法 |
| DE4332048A1 (de) * | 1993-09-21 | 1995-03-23 | Hoechst Ag | Mischungen von Farbstoffen mit faserreaktiven Gruppen und deren Verwendung zum Färben von Fasermaterialien |
| GB9714010D0 (en) * | 1997-07-03 | 1997-09-10 | Zeneca Ltd | Composition |
| US5972084A (en) * | 1997-06-17 | 1999-10-26 | Ciba Specialty Chemicals Corporation | Process for printing textile fiber materials in accordance with the ink-jet printing process |
| JPH11315483A (ja) * | 1998-03-04 | 1999-11-16 | Dystar Textilfarben Gmbh & Co Deutsche Kg | アルカリ性水溶液およびかかる水溶液のセルロ―ス系繊維材料染色プロセスにおける使用 |
| US6530961B1 (en) * | 1998-03-04 | 2003-03-11 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Alkaline aqueous solutions and use thereof in processes for dyeing cellulosic textile materials |
| DE19810906A1 (de) * | 1998-03-13 | 1999-09-16 | Basf Ag | Reaktivfarbstoffe mit einem Kombinationsanker |
| CN1339052A (zh) * | 1999-02-05 | 2002-03-06 | 西巴特殊化学品控股有限公司 | 黑色染色油墨及其用途 |
| ES2185549T3 (es) * | 1999-09-27 | 2003-05-01 | Ciba Sc Holding Ag | Tintas de color rojo carmesi (magenta) que contienen colorantes azoicos de complejo de cobre basados en acidos 1-naftol-di- o -trisulfonicos. |
| 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 |
| US6815536B2 (en) * | 2002-10-17 | 2004-11-09 | Everlight Usa, Inc. | Monoazo reactive red dyestuff |
-
2001
- 2001-09-27 KR KR1020037005020A patent/KR100814209B1/ko not_active Expired - Fee Related
- 2001-09-27 PT PT01967626T patent/PT1332181E/pt unknown
- 2001-09-27 DE DE60139949T patent/DE60139949D1/de not_active Expired - Lifetime
- 2001-09-27 JP JP2002534431A patent/JP2004511610A/ja active Pending
- 2001-09-27 US US10/398,557 patent/US6974497B2/en not_active Expired - Fee Related
- 2001-09-27 BR BRPI0114476-6A patent/BR0114476B1/pt not_active IP Right Cessation
- 2001-09-27 ES ES01967626T patent/ES2329876T3/es not_active Expired - Lifetime
- 2001-09-27 AT AT01967626T patent/ATE443108T1/de not_active IP Right Cessation
- 2001-09-27 CN CNB018170005A patent/CN1325573C/zh not_active Expired - Fee Related
- 2001-09-27 MX MXPA03002684A patent/MXPA03002684A/es active IP Right Grant
- 2001-09-27 EP EP01967626A patent/EP1332181B1/en not_active Expired - Lifetime
- 2001-09-27 WO PCT/IB2001/001783 patent/WO2002031057A2/en not_active Ceased
- 2001-10-09 TW TW090124932A patent/TW593559B/zh not_active IP Right Cessation
-
2003
- 2003-02-28 ZA ZA200301716A patent/ZA200301716B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002031057A9 (en) | 2003-05-08 |
| BR0114476B1 (pt) | 2012-12-11 |
| CN1496389A (zh) | 2004-05-12 |
| CN1325573C (zh) | 2007-07-11 |
| EP1332181A2 (en) | 2003-08-06 |
| PT1332181E (pt) | 2009-11-11 |
| US6974497B2 (en) | 2005-12-13 |
| US20040137565A1 (en) | 2004-07-15 |
| MXPA03002684A (es) | 2003-10-15 |
| DE60139949D1 (de) | 2009-10-29 |
| ZA200301716B (en) | 2004-02-26 |
| JP2004511610A (ja) | 2004-04-15 |
| ATE443108T1 (de) | 2009-10-15 |
| KR100814209B1 (ko) | 2008-03-17 |
| ES2329876T3 (es) | 2009-12-02 |
| WO2002031057A2 (en) | 2002-04-18 |
| BR0114476A (pt) | 2003-08-19 |
| WO2002031057A3 (en) | 2002-09-12 |
| KR20030041159A (ko) | 2003-05-23 |
| EP1332181B1 (en) | 2009-09-16 |
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