DE3443962A1 - Reaktive disazoverbindungen - Google Patents
Reaktive disazoverbindungenInfo
- Publication number
- DE3443962A1 DE3443962A1 DE19843443962 DE3443962A DE3443962A1 DE 3443962 A1 DE3443962 A1 DE 3443962A1 DE 19843443962 DE19843443962 DE 19843443962 DE 3443962 A DE3443962 A DE 3443962A DE 3443962 A1 DE3443962 A1 DE 3443962A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- nr1r2
- compounds
- radical
- dyeing
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 238000004043 dyeing Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229920000742 Cotton Polymers 0.000 claims abstract description 9
- 230000008878 coupling Effects 0.000 claims abstract description 9
- 238000010168 coupling process Methods 0.000 claims abstract description 9
- 238000005859 coupling reaction Methods 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000000758 substrate Substances 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000004753 textile Substances 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 239000004952 Polyamide Substances 0.000 claims abstract description 3
- 239000010985 leather Substances 0.000 claims abstract description 3
- 229920002647 polyamide Polymers 0.000 claims abstract description 3
- 239000004627 regenerated cellulose Substances 0.000 claims abstract description 3
- 239000000975 dye Substances 0.000 claims description 28
- 150000001412 amines Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000000985 reactive dye Substances 0.000 abstract description 6
- -1 for example Chemical compound 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 3
- ORLGPUVJERIKLW-UHFFFAOYSA-N 5-chlorotriazine Chemical group ClC1=CN=NN=C1 ORLGPUVJERIKLW-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 150000001768 cations Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 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 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 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
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 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 description 3
- 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 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910001413 alkali metal ion Inorganic materials 0.000 description 2
- 239000007844 bleaching agent 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
- 238000001035 drying Methods 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
- 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
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [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 compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 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 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring 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
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
- C09B62/02—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
-
- 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
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843443962 DE3443962A1 (de) | 1983-12-10 | 1984-12-01 | Reaktive disazoverbindungen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3344718 | 1983-12-10 | ||
| DE19843443962 DE3443962A1 (de) | 1983-12-10 | 1984-12-01 | Reaktive disazoverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3443962A1 true DE3443962A1 (de) | 1985-06-20 |
| DE3443962C2 DE3443962C2 (en, 2012) | 1989-03-09 |
Family
ID=25816335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843443962 Granted DE3443962A1 (de) | 1983-12-10 | 1984-12-01 | Reaktive disazoverbindungen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3443962A1 (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0651027A1 (en) * | 1993-10-30 | 1995-05-03 | Sandoz Ltd. | Disazo dyestuffs of the stilbene series |
| WO2005116144A1 (en) * | 2004-05-24 | 2005-12-08 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Mixtures of fibre reactive azo dyes |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151625B (de) * | 1956-09-14 | 1963-07-18 | Ciba Geigy | Verfahren zur Herstellung von Disazofarbstoffen |
| EP0022489A1 (de) * | 1979-07-14 | 1981-01-21 | BASF Aktiengesellschaft | Pulverförmige Farbstoffzubereitung |
| GB2066282A (en) * | 1979-12-21 | 1981-07-08 | Sandoz Ltd | Reactive diazo dyestuffs |
| 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 |
| EP0170612A1 (de) * | 1984-07-03 | 1986-02-05 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
-
1984
- 1984-12-01 DE DE19843443962 patent/DE3443962A1/de active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1151625B (de) * | 1956-09-14 | 1963-07-18 | Ciba Geigy | Verfahren zur Herstellung von Disazofarbstoffen |
| EP0022489A1 (de) * | 1979-07-14 | 1981-01-21 | BASF Aktiengesellschaft | Pulverförmige Farbstoffzubereitung |
| GB2066282A (en) * | 1979-12-21 | 1981-07-08 | Sandoz Ltd | Reactive diazo dyestuffs |
| 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 |
| EP0170612A1 (de) * | 1984-07-03 | 1986-02-05 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
Non-Patent Citations (1)
| Title |
|---|
| Bei der Patenterteilung wurde ein Versuchsbericht mit einer Färbemustertafel zur Einsicht für jedermann bereitgehalten |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5495003A (en) * | 1993-01-30 | 1996-02-27 | Sandoz Ltd. | 2,2'-disulfo-4,4'-substituted triazinylaminophenyl disazostilbenes |
| EP0651027A1 (en) * | 1993-10-30 | 1995-05-03 | Sandoz Ltd. | Disazo dyestuffs of the stilbene series |
| TR27925A (tr) * | 1993-10-30 | 1995-10-16 | Sandoz Ltd | Stilben serisinden disazo boyarmaddeler. |
| WO2005116144A1 (en) * | 2004-05-24 | 2005-12-08 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Mixtures of fibre reactive azo dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3443962C2 (en, 2012) | 1989-03-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CLARIANT FINANCE (BVI) LTD., TORTOLA, VG |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: SPOTT WEINMILLER & PARTNER, 80336 MUENCHEN |