CH237728A - Process for the preparation of a water-soluble dye. - Google Patents
Process for the preparation of a water-soluble dye.Info
- Publication number
- CH237728A CH237728A CH237728DA CH237728A CH 237728 A CH237728 A CH 237728A CH 237728D A CH237728D A CH 237728DA CH 237728 A CH237728 A CH 237728A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- process according
- preparation
- soluble dye
- toluidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 7
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 239000000395 magnesium oxide Substances 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000004682 monohydrates Chemical class 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- YBDBYPQFIMSFJW-UHFFFAOYSA-N (4-chloro-3-nitrophenyl)-phenylmethanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2C=CC=CC=2)=C1 YBDBYPQFIMSFJW-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WUBANEGQSXTPHM-UHFFFAOYSA-N [4-(4-chloro-3-nitrobenzoyl)phenyl]-(4-chloro-3-nitrophenyl)methanone Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C(=O)C=2C=CC(=CC=2)C(=O)C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)=C1 WUBANEGQSXTPHM-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B51/00—Nitro or nitroso dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 234351. Verfahren zur Herstellung eines wasserlöslichen Farbstoffes. Gegenstand dieses Patentes ist ein Ver fahren zur Herstellung eines wasserlöslichen Farbstoffes, welches darin besteht, dass man ein Mol 1.4-Di-(4'-chlor-3'-nitrobenzoyl)-ben- zol mit zwei Mol p-Toluidin umsetzt und das erhaltene Kondensationsprodukt sulfoniert. Dabei treten zwei Sulfogruppen in das Mole kül ein.
Die Umsetzung erfolgt zweckmässig durch Erhitzen dieser Verbindungen in Gegenwart eines Lösungsmittels und eines säurebindenden Mittels, z. B. Natriumcarbonat, Natriumacetat oder Magnesiumoxyd. Man kann für die Kon densation als Lösungsmittel auch einen Über schuss des für die Kondensation verwendeten Amins benutzen.
<I>Beispiel:</I> 1 Gewichtsteil 1.4-Di-(4'-chlor-3'-nitro- benzoyl)-benzol (erhältlich nach bekannten Verfahren durch Einwirkung von überschüs sigem Halogenbenzol auf Terephthaloylchlorid in Gegenwart von Aluminiumchlorid und nach- trägliche Nitrierung) wird mit 5 Gewichts- teilen p-Toluidin, 0.15 Gewichtsteilen Ma- gnesiümoxyd 6-8 Stunden auf 120-125 erhitzt.
Das zu einem Kristallbrei erstarrte Kondensationsprodukt wird mit Alkohol ver dünnt und abgesaugt und durch Waschen mit Wasser und verdünnter Salzsäure gereinigt.
Man sulfoniert die so erhaltene Verbindung durch Behandeln mit der 6-7fachen Menge Monohydrat bei 25-30 so lange, bis eine Probe in überschüssigem verdünntem Alkali hydroxyd löslich ist. Die Abscheidung der so gebildeten Farbstoffsulfonsäure erfolgt in der üblichen Weise. Sie färbt Wolle in sehr klaren gelben Tönen von ausgezeichneten Echtheits eigenschaften.
Additional patent to main patent no. 234351. Process for the production of a water-soluble dye. The subject of this patent is a process for the production of a water-soluble dye, which consists in that one mole of 1,4-di- (4'-chloro-3'-nitrobenzoyl) benzene is reacted with two moles of p-toluidine and the resultant Sulfonated condensation product. Two sulfo groups enter the mole kül.
The reaction is conveniently carried out by heating these compounds in the presence of a solvent and an acid-binding agent, e.g. B. sodium carbonate, sodium acetate or magnesium oxide. You can also use an excess of the amine used for the condensation as a solvent for the condensation.
<I> Example: </I> 1 part by weight of 1,4-di- (4'-chloro-3'-nitro-benzoyl) -benzene (obtainable according to known processes by the action of excess halobenzene on terephthaloyl chloride in the presence of aluminum chloride and after- subsequent nitration) is heated to 120-125 for 6-8 hours with 5 parts by weight of p-toluidine, 0.15 part by weight of magnesium oxide.
The condensation product, which has solidified to form a crystal slurry, is diluted with alcohol and filtered off with suction and purified by washing with water and dilute hydrochloric acid.
The compound obtained in this way is sulfonated by treating it with 6-7 times the amount of monohydrate at 25-30 until a sample is soluble in excess dilute alkali hydroxide. The dye sulfonic acid thus formed is deposited in the usual way. It dyes wool in very clear yellow shades with excellent fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH234351T | 1943-04-19 | ||
| CH237728T | 1943-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237728A true CH237728A (en) | 1945-05-15 |
Family
ID=25727861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237728D CH237728A (en) | 1943-04-19 | 1943-04-19 | Process for the preparation of a water-soluble dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237728A (en) |
-
1943
- 1943-04-19 CH CH237728D patent/CH237728A/en unknown
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