CH209973A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH209973A CH209973A CH209973DA CH209973A CH 209973 A CH209973 A CH 209973A CH 209973D A CH209973D A CH 209973DA CH 209973 A CH209973 A CH 209973A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- azo dye
- carboxylic acid
- preparation
- acid group
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Azofarb'stoffes. Es wurde gefunden, dass man einen Azo- farbstoff erhält, wenn man den Farbstoff aus diazotiertem 1-Aminobenzol-4-p-oxyäthyläther und 1-Phenyl-3-methyl-5-pyrazolon derart mit Maleinsäureanhydrid behandelt,
dass die Oxy- gruppe des Farbstoffes mit einer Carbonsäure- gruppe der Maleinsäure verestert wird und die andere Carbonsäuregruppe zur Salzbil dung frei bleibt.
Der so erhaltene Farbstoff bildet ein gelbes Pulver, das in Form eines Alkali- salzes in Wasser löslich ist und das aus wässriger Lösung Aoetatkunstseide in gelben Tönen färbt.
<I>Beispiel:</I> <B>5</B> Teile des Farbstoffes, den man durch Vereinigen der Diazoverbindung des 1-Amino- benzol-4-p-oxyäthyläthers mit 1-Phenyl-3- methyl-5-pyrazolon erhält, werden in etwa <B>5</B> Teilen geschmolzenes Maleinsäureanhydrid eingetragen. Man rührt nun die Masse bei einer Temperatur von etwa<B>80-90</B> 11 so lange, bis eine klare Schmelze entsteht. Durch Auf nahme in Wasser und Neutralisieren mit einem Alkali, z.
B. Ammoniumhydroxyd oder Natriumearbonat erhält man eine tief gelbe Lösung des neuen Parbstoffes. Durch Ver setzen mit einem Salz, zum Beispiel mit Natriumehlorid, fällt der Farbstoff aus. Er wird abfiltriert und getrocknet.
Process for the production of an azo dye. It has been found that an azo dye is obtained if the dye from diazotized 1-aminobenzene-4-p-oxyethyl ether and 1-phenyl-3-methyl-5-pyrazolone is treated with maleic anhydride in such a way that
that the oxy group of the dye is esterified with a carboxylic acid group of maleic acid and the other carboxylic acid group remains free for salt formation.
The dye thus obtained forms a yellow powder which is soluble in water in the form of an alkali salt and which, from aqueous solution, dyes acetate silk in yellow tones.
<I> Example: </I> <B> 5 </B> parts of the dye that can be obtained by combining the diazo compound of 1-amino-benzene-4-p-oxyethyl ether with 1-phenyl-3-methyl-5- pyrazolone is obtained, about <B> 5 </B> parts of molten maleic anhydride are introduced. The mass is then stirred at a temperature of about 80-90 11 until a clear melt is formed. By taking up in water and neutralizing with an alkali, e.g.
B. ammonium hydroxide or sodium carbonate gives a deep yellow solution of the new paraffin. The dye is precipitated by adding a salt, for example sodium chloride. It is filtered off and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH209973T | 1938-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209973A true CH209973A (en) | 1940-05-31 |
Family
ID=4446743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209973D CH209973A (en) | 1938-09-22 | 1938-09-22 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209973A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158596A (en) * | 1957-09-27 | 1964-11-24 | Ciba Ltd | Water-soluble organic dyestuffs |
-
1938
- 1938-09-22 CH CH209973D patent/CH209973A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158596A (en) * | 1957-09-27 | 1964-11-24 | Ciba Ltd | Water-soluble organic dyestuffs |
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