AT390441B - Verfahren zur herstellung von reaktiven disazoverbindungen und ihre verwendung - Google Patents
Verfahren zur herstellung von reaktiven disazoverbindungen und ihre verwendung Download PDFInfo
- Publication number
- AT390441B AT390441B AT0389084A AT389084A AT390441B AT 390441 B AT390441 B AT 390441B AT 0389084 A AT0389084 A AT 0389084A AT 389084 A AT389084 A AT 389084A AT 390441 B AT390441 B AT 390441B
- Authority
- AT
- Austria
- Prior art keywords
- parts
- dyeing
- dye
- minutes
- cotton
- Prior art date
Links
- LCZPIYCNOWJWPQ-UHFFFAOYSA-I disodium;chromium(3+);1-[(2-oxidonaphthalen-1-yl)diazenyl]-4-sulfonaphthalen-2-olate;3-oxido-4-[(2-oxidonaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].[Cr+3].C12=CC=CC=C2C(S(=O)(=O)O)=CC([O-])=C1N=NC1=C([O-])C=CC2=CC=CC=C12.C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3[O-])=C([O-])C=C(S([O-])(=O)=O)C2=C1 LCZPIYCNOWJWPQ-UHFFFAOYSA-I 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 25
- 238000004043 dyeing Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 12
- 229920000742 Cotton Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 239000010446 mirabilite Substances 0.000 claims description 3
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 2
- WTIFIAZWCCBCGE-UUOKFMHZSA-N guanosine 2'-monophosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OP(O)(O)=O WTIFIAZWCCBCGE-UUOKFMHZSA-N 0.000 claims 2
- 239000004744 fabric Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 claims 1
- 150000001768 cations Chemical class 0.000 description 7
- 239000000985 reactive dye Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 ammonium ions Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical group ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/01—Mixtures of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3344718 | 1983-12-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA389084A ATA389084A (de) | 1989-10-15 |
| AT390441B true AT390441B (de) | 1990-05-10 |
Family
ID=6216598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0389084A AT390441B (de) | 1983-12-10 | 1984-12-07 | Verfahren zur herstellung von reaktiven disazoverbindungen und ihre verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5095101A (en, 2012) |
| JP (1) | JPS60141765A (en, 2012) |
| AT (1) | AT390441B (en, 2012) |
| CH (1) | CH658463A5 (en, 2012) |
| FR (1) | FR2556358B1 (en, 2012) |
| GB (1) | GB2151251B (en, 2012) |
| HK (1) | HK75290A (en, 2012) |
| IT (1) | IT1199237B (en, 2012) |
| SG (1) | SG40790G (en, 2012) |
| ZA (1) | ZA849598B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5188640A (en) * | 1983-12-10 | 1993-02-23 | Sandoz Ltd. | Use of 1-amino-2,7-di-[5'-((2"-chloro-4"-substituted amino-1,3,5-triazin-6-ylamino)-2'-sulfophenylazo]-8-hydroxynaphthalene-3,6-disulfonic acids for dyeing and printing |
| FR2640988B1 (en, 2012) * | 1988-12-22 | 1993-02-19 | Sandoz Sa | |
| DE4337181A1 (de) * | 1993-10-30 | 1995-05-04 | Sandoz Ag | Disazofarbstoffe der Stilbenreihe |
| JP2001002952A (ja) * | 1999-04-19 | 2001-01-09 | Sumitomo Chem Co Ltd | ビスアゾ化合物又はその塩及びそれらの繊維材料への適用 |
| JP4501200B2 (ja) * | 2000-01-21 | 2010-07-14 | 住友化学株式会社 | 反応染料組成物およびそれを用いる染色法 |
| GB0411589D0 (en) * | 2004-05-24 | 2004-06-23 | Dystar Textilfarben Gmbh & Co | Mixtures of fibre reactive azo dyes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1220823A (en) * | 1967-07-21 | 1971-01-27 | Ici Ltd | New disazo dyestuffs |
| EP0048355A1 (de) * | 1980-09-06 | 1982-03-31 | Hoechst Aktiengesellschaft | Wasserlösliche Disazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1543282A (fr) * | 1966-08-01 | 1968-10-25 | Ici Ltd | Colorants azoïques solubles dans l'eau et leur procédé de fabrication |
| US3663526A (en) * | 1969-10-15 | 1972-05-16 | Ciba Geigy Ag | Disazo dyes containing an alkoxy-halogen-triazine group |
| GB1387925A (en) * | 1972-05-24 | 1975-03-19 | Ici Ltd | Colouration process |
| JPS5511708B2 (en, 2012) * | 1972-10-16 | 1980-03-27 | ||
| GB1473062A (en) * | 1975-01-20 | 1977-05-11 | Ici Ltd | Colouration process |
| LU75689A1 (en, 2012) * | 1976-08-31 | 1978-04-13 | ||
| DE2647312A1 (de) * | 1976-10-20 | 1978-04-27 | Bayer Ag | Reaktivfarbstoffe |
| JPS53117024A (en) * | 1977-03-24 | 1978-10-13 | Nippon Kayaku Co Ltd | Bis-azo compounds, their preparation, and dyeing of cellulosic fibrous materials with them |
| JPS5594964A (en) * | 1979-01-11 | 1980-07-18 | Nippon Kayaku Co Ltd | New reactive azo compound, preparing same and dyeing by using same |
| DE2928508A1 (de) * | 1979-07-14 | 1981-01-29 | Basf Ag | Pulverfoermige farbstoffzubereitung |
| EP0040460A1 (en) * | 1980-05-21 | 1981-11-25 | Imperial Chemical Industries Plc | Reactive dyes |
| JPS5725359A (en) * | 1980-06-20 | 1982-02-10 | Ciba Geigy Ag | Manufacture of disazo dye |
| CH646989A5 (de) * | 1980-10-07 | 1984-12-28 | Sandoz Ag | Unsymmetrische halo-triazinyl-verbindungen. |
| DE3476218D1 (en) * | 1983-02-24 | 1989-02-23 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| DE3325788A1 (de) * | 1983-03-15 | 1984-09-20 | Bayer Ag, 5090 Leverkusen | Faserreaktive disazofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben oder bedrucken von stubstraten |
| ATE43356T1 (de) * | 1984-07-03 | 1989-06-15 | Ciba Geigy Ag | Reaktivfarbstoffe, deren herstellung und verwendung. |
-
1984
- 1984-12-03 FR FR8418499A patent/FR2556358B1/fr not_active Expired
- 1984-12-07 AT AT0389084A patent/AT390441B/de not_active IP Right Cessation
- 1984-12-07 IT IT49267/84A patent/IT1199237B/it active
- 1984-12-07 GB GB08430989A patent/GB2151251B/en not_active Expired
- 1984-12-07 CH CH5820/84A patent/CH658463A5/de not_active IP Right Cessation
- 1984-12-08 JP JP59258479A patent/JPS60141765A/ja active Granted
- 1984-12-10 ZA ZA849598A patent/ZA849598B/xx unknown
-
1988
- 1988-07-14 US US07/219,422 patent/US5095101A/en not_active Expired - Lifetime
-
1990
- 1990-06-11 SG SG407/90A patent/SG40790G/en unknown
- 1990-09-20 HK HK752/90A patent/HK75290A/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1220823A (en) * | 1967-07-21 | 1971-01-27 | Ici Ltd | New disazo dyestuffs |
| EP0048355A1 (de) * | 1980-09-06 | 1982-03-31 | Hoechst Aktiengesellschaft | Wasserlösliche Disazoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0564185B2 (en, 2012) | 1993-09-14 |
| ZA849598B (en) | 1986-02-26 |
| GB8430989D0 (en) | 1985-01-16 |
| GB2151251A (en) | 1985-07-17 |
| US5095101A (en) | 1992-03-10 |
| SG40790G (en) | 1990-08-03 |
| CH658463A5 (de) | 1986-11-14 |
| IT8449267A0 (it) | 1984-12-07 |
| GB2151251B (en) | 1987-09-03 |
| IT8449267A1 (it) | 1986-06-07 |
| HK75290A (en) | 1990-09-28 |
| FR2556358A1 (fr) | 1985-06-14 |
| ATA389084A (de) | 1989-10-15 |
| FR2556358B1 (fr) | 1987-01-02 |
| JPS60141765A (ja) | 1985-07-26 |
| IT1199237B (it) | 1988-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EIH | Change in the person of patent owner | ||
| ELA | Expired due to lapse of time |