CH211804A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211804A CH211804A CH211804DA CH211804A CH 211804 A CH211804 A CH 211804A CH 211804D A CH211804D A CH 211804DA CH 211804 A CH211804 A CH 211804A
- Authority
- CH
- Switzerland
- Prior art keywords
- methoxy
- methyl
- azo dye
- diazo
- preparation
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 4
- FADWLJVAKGATER-UHFFFAOYSA-N n-(2-ethoxyethyl)-2-methoxy-5-methylaniline Chemical compound CCOCCNC1=CC(C)=CC=C1OC FADWLJVAKGATER-UHFFFAOYSA-N 0.000 claims description 4
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- -1 maleic acid ester Chemical class 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 229920002955 Art silk Polymers 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 239000000243 solution Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring 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
- 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)
Description
Zusatzpatent zum Hauptpatent Nr. 208950. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen wertvollen Azofarbstoff erhält, wenn man 5- Methyl - 2 - methoxy-N- äthyloxyäthylamino- benzol, die Diazoverbindung des 1-Amino-2- chlor-4-nitrobenzols und Maleinsäureanhy- drid derart aufeinander einwirken lässt,
dass der saure Maleinsäureester des 5-Methyl-2- methoxy-N-äthyloxyäthylaminobenzols ge bildet wird und der Diazorest in 4-Stellung zur tertiären Aminogruppe eintritt.
Der so erhaltene Farbstoff bildet ein dunkles Pulver, das sich in Form eines Al kalisalzes in Wasser mit violetter Farbe löst und Acetatkunstseide aus wässeriger Lösung in violetten Tönen färbt. <I>Beispiel:</I> in die Diazolösung, die man aus 172,5 Teilen 1-Amino-2-chlor-4-nitrobenzol herstellt, trägt man 307 Teile des sauren Maleinsäure- esters des 5-Methyl-2-methoxy-N-äthyloxy- äthylaminobenzols,
erhalten durch Umset- zung von Maleinsäureanhydrid mit 5-Methyl- 2-methoxy-N-äthyloxyäthylaminobenzol, der in Form einer wässerigen Lösung seines Am moniumsalzes vorliegt, ein. Man führt die Kupplung durch längeres Rühren zu Ende und kann auch allenfalls neutralisierende Mittel, wie z. B. Natriumacetat zugeben. Der Farbstoff wird dann abfiltriert und etwas mit Wasser gewaschen.
Man verrührt ihn dann mit einer Natriumchloridlösung und stellt mit Natriumcarbonat oder mit Ammo niak auf den Neutralpunkt.
Additional patent to main patent no. 208950. Process for the production of an azo dye. It has been found that a new valuable azo dye is obtained if 5-methyl-2-methoxy-N-ethyloxyethylamino-benzene, the diazo compound of 1-amino-2-chloro-4-nitrobenzene and maleic anhydride are allowed to act on one another in this way ,
that the acidic maleic acid ester of 5-methyl-2-methoxy-N-äthyloxyäthylaminobenzols is formed and the diazo radical occurs in the 4-position to the tertiary amino group.
The dye obtained in this way forms a dark powder that dissolves in the form of an alkali salt in water with a violet color and dyes acetate artificial silk from an aqueous solution in violet tones. <I> Example: </I> the diazo solution, which is prepared from 172.5 parts of 1-amino-2-chloro-4-nitrobenzene, contains 307 parts of the acidic maleic acid ester of 5-methyl-2-methoxy -N-äthyloxy- äthylaminobenzols,
obtained by reacting maleic anhydride with 5-methyl-2-methoxy-N-ethyloxyethylaminobenzene, which is in the form of an aqueous solution of its ammonium salt. The coupling is completed by prolonged stirring and, if necessary, neutralizing agents, such as. B. Add sodium acetate. The dye is then filtered off and washed a little with water.
It is then stirred with a sodium chloride solution and adjusted to the neutral point with sodium carbonate or with ammonia.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208950T | 1937-09-18 | ||
| CH211804T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211804A true CH211804A (en) | 1940-10-15 |
Family
ID=25724595
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211804D CH211804A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211804A (en) |
-
1937
- 1937-09-18 CH CH211804D patent/CH211804A/en unknown
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