CH211817A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211817A CH211817A CH211817DA CH211817A CH 211817 A CH211817 A CH 211817A CH 211817D A CH211817D A CH 211817DA CH 211817 A CH211817 A CH 211817A
- Authority
- CH
- Switzerland
- Prior art keywords
- methoxy
- methyl
- azo dye
- preparation
- dye
- 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 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 229920002955 Art silk Polymers 0.000 claims 1
- 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
- 229920000297 Rayon Polymers 0.000 description 1
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> 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-äthyloxäthylaminoben- zol, die Diazoverbindung des 1-Amino-4- nitrobenzols und Maleinsäureanhydrid derart aufeinander einwirken lässt,
dass der saure Maleinsäureester des 5-Methyl-2-methoxy-N- äthyloxäthylaminobenzols gebildet 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 roter Farbe löst und Acetatkunstseide aus wässriger Lösung in roten Tönen färbt.
<I>Beispiel:</I> In die Diazolösung, die man aus 139 Tei len 1-Amino-4-nitrobenzol herstellt, trägt man 307 Teile des sauren Maleinsäureesters des 5-Methyl- 2 -methoxy- N- äthyloxäthylamino- benzols, erhalten durch Umsetzung von Maleinsäureanhydrid mit 5 - Methyl - 2 - me- thoxy - N - äthyloxäthylaminobenzol,
der in Form einer wässrigen Lösung eines Ammo- niumsalzes vorliegt, ein. Man führt die Kupp lung durch längeres Rühren zu Ende und kann auch allenfalls neutralisierende Mittel, wie z. B. Natriumacetat, zugeben. Der Farb stoff wird dann abfiltriert und etwas mit Wasser gewaschen. Man verrührt ihn dann mit einer Natriumchloridlösung und stellt mit Natriumcarbonat oder mit Ammoniak auf den Neutralpunkt.
<B> Additional patent </B> 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-ethyloxethylaminobenzene, the diazo compound of 1-amino-4-nitrobenzene and maleic anhydride are allowed to act on one another in such a way that
that the acidic maleic acid ester of 5-methyl-2-methoxy-N-äthyloxäthylaminobenzols is formed and the diazo radical occurs in the 4-position to the tertiary amino group.
The dye thus obtained forms a dark powder which dissolves in the form of an alkali salt in water with a red color and dyes acetate rayon from aqueous solution in red tones.
<I> Example: </I> In the diazo solution, which is produced from 139 parts of 1-amino-4-nitrobenzene, one carries 307 parts of the acidic maleic acid ester of 5-methyl-2-methoxy-N-ethyloxethylamino-benzene, obtained by reacting maleic anhydride with 5 - methyl - 2 - methoxy - N - äthyloxäthylaminobenzol,
which is in the form of an aqueous solution of an ammonium salt. You lead the hitch ment by prolonged stirring to the end and, if necessary, neutralizing agents such. B. sodium acetate, add. The dye is then filtered off and washed a little with water. It is then stirred with a sodium chloride solution and set to neutral with sodium carbonate or ammonia.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH208950T | 1937-09-18 | ||
| CH211817T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211817A true CH211817A (en) | 1940-10-15 |
Family
ID=25724608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211817D CH211817A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211817A (en) |
-
1937
- 1937-09-18 CH CH211817D patent/CH211817A/en unknown
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