CH298759A - Process for the production of an acidic wool dye. - Google Patents
Process for the production of an acidic wool dye.Info
- Publication number
- CH298759A CH298759A CH298759DA CH298759A CH 298759 A CH298759 A CH 298759A CH 298759D A CH298759D A CH 298759DA CH 298759 A CH298759 A CH 298759A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- acidic
- good
- dye
- ethoxybenzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 210000002268 wool Anatomy 0.000 title claims description 7
- 230000002378 acidificating effect Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000975 dye Substances 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- KTFUNVBAGAPLLC-UHFFFAOYSA-N 2-amino-5-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(N)C(S(O)(=O)=O)=C1 KTFUNVBAGAPLLC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- MXMRPGUGGAIURA-UHFFFAOYSA-N 2-(4-chlorophenyl)-4,6-dimethyl-1-(2-methylpropyl)indole Chemical compound C(C(C)C)N1C(=CC2=C(C=C(C=C12)C)C)C1=CC=C(C=C1)Cl MXMRPGUGGAIURA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- -1 4,4'-dichlorobenzophenone ketochloride Chemical compound 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 296669. Verfahren zur Herstellung eines sauren Wollfarbstoffes. Gegenstand dieses Patentes ist ein Verfah ren zur Herstellung eines sauren Wollfarb- stoffes, welches darin besteht, dass man 1 Mol der durch Kondensation von 1 Mol 4.4'-Di- chlorbenzophenon mit 1 Mol N-IsobLltyl-2-(p- Chlorphenyl)
-4.6-dimethylindol erhältlichen Verbindung mit 2 Mol 1-Amino-4-äthoxyben- zol-2-sulfonsäure umsetzt.
Die Umsetzung erfolgt durch- Erhitzen der Ausgangsstoffe mit oder ohne Zusatz von Lö- sungs- oder Schmelzmitteln, z. B. unter Zusatz von Glykol oder ähnlichen Verbindungen. Man kann zum Beispiel Temperaturen von 100 bis 1.60 C anwenden. Die 1-Amino-4-äthoxyben- zol-2-sulfonsäure wird als freie Säure oder in Form ihrer Alkali- oder Ammoniumsalze ver wendet.
Der neue Farbstoff färbt Wolle in sehr klaren grünstickig blauen Tönen von guter Lichtechtheit und schöner Abendfarbe. Er be sitzt ein gutes Egalisierungsvermögen, gutes Ziehvermögen aus saurem und neutralem Bade.
Beispiel: 8,4 g 4.4'-Dichlorbenzophenonketochlorid werden init 7,5 g N-Isobutvl-2-(p-chlorphe- nyl)-4.6-dimethylindol, 4 g Zinkchlorid und 3 g 1.2-Dichlorbenzol 8 bis 10 Stunden bei 95 bis 105 C verrührt. Die im Laufe dieser Zeit immer zäher werdende Schmelze enthält eine tiefrote Kondensationsverbindung, die sich in Eisessig oder konzentrierter Schwefelsäure mit tiefroter Farbe löst.
Die so erhaltene Schmelze wird mit 100 g Glykol verdünnt und nach Zusatz von 40 g des Natrium-, Kalium- oder ÄmmoniLunsalzes der 1- Amino-4-äthoxybenzol-2-sulfonsäure 5 bis 7 StLlnden bei 130 bis 150 C verrührt. Die Schmelze wird auf etwa 100 C abgekühlt und in Eiswasser ausgetragen.
Die beim Ausgiessen in Wasser ausfallende FarbstoVdis-Lilfonsäure wird abfiltriert, durch Auswaschen mit kaltem Wasser gereinigt, dann in warmem Wasser unter Zusatz der hinreichenden Menge NatriLnncarbonat gelöst, die Lösung wird mit 10 bis 15 g eines geeig neten Netzmittels versetzt und aus der Lösung dann der Farbstoff durch Natriumchlorid ge fällt.
Der so erhaltene blaue Farbstoff stellt eine Disulfonsäure von folgender Zusammen- setztui.g dar
EMI0002.0001
Der neue Farbstoff färbt Wolle in sehr klaren grünstichig blauen Tönen von. guter Lichtechtheit und schöner Abendfarbe. Er be sitzt ein gutes Egalisierungsvermögen lind g<B>01</B> utes Ziehvermögen aus neutralem Bade.
<B> Additional patent </B> to main patent no. 296669. Process for the production of an acidic wool dye. The subject of this patent is a process for the production of an acidic wool dye, which consists in that 1 mol of the condensation of 1 mol of 4,4'-dichlorobenzophenone with 1 mol of N-IsobLltyl-2- (p-chlorophenyl)
-4.6-dimethylindole available compound with 2 moles of 1-amino-4-ethoxybenzene-2-sulfonic acid is reacted.
The reaction takes place by heating the starting materials with or without the addition of solvents or fluxes, e.g. B. with the addition of glycol or similar compounds. For example, temperatures from 100 to 1.60 C can be used. 1-Amino-4-ethoxybenzene-2-sulfonic acid is used as the free acid or in the form of its alkali metal or ammonium salts.
The new dye dyes wool in very clear greenish blue shades of good lightfastness and a beautiful evening color. He has a good leveling power, good drawing power from acidic and neutral baths.
Example: 8.4 g of 4,4'-dichlorobenzophenone ketochloride are mixed with 7.5 g of N-isobutyl-2- (p-chlorophenyl) -4,6-dimethylindole, 4 g of zinc chloride and 3 g of 1,2-dichlorobenzene for 8 to 10 hours at 95 to 105 C. The melt, which becomes increasingly viscous in the course of this time, contains a deep red condensation compound that dissolves in glacial acetic acid or concentrated sulfuric acid with a deep red color.
The melt obtained in this way is diluted with 100 g of glycol and, after the addition of 40 g of the sodium, potassium or ammonium salt of 1-amino-4-ethoxybenzene-2-sulfonic acid, stirred for 5 to 7 hours at 130 to 150.degree. The melt is cooled to about 100 ° C. and discharged into ice water.
The dyestuff disilfonic acid which precipitates out when pouring into water is filtered off, cleaned by washing with cold water, then dissolved in warm water with the addition of a sufficient amount of sodium carbonate, the solution is mixed with 10 to 15 g of a suitable wetting agent and then the solution is removed Dye is precipitated by sodium chloride.
The blue dye thus obtained is a disulfonic acid with the following composition
EMI0002.0001
The new dye dyes wool in very clear greenish blue tones of. good lightfastness and beautiful evening color. It has good equalizing properties and good drawability from neutral baths.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE298759X | 1942-05-30 | ||
| DE130642X | 1942-06-13 | ||
| CH296669T | 1943-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH298759A true CH298759A (en) | 1954-05-15 |
Family
ID=27178240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH298759D CH298759A (en) | 1942-05-30 | 1943-03-30 | Process for the production of an acidic wool dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH298759A (en) |
-
1943
- 1943-03-30 CH CH298759D patent/CH298759A/en unknown
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