CH211820A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211820A CH211820A CH211820DA CH211820A CH 211820 A CH211820 A CH 211820A CH 211820D A CH211820D A CH 211820DA CH 211820 A CH211820 A CH 211820A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- dye
- preparation
- diazo
- butyloxethylaminobenzene
- 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
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007864 aqueous solution Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 2
- 229920000297 Rayon 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
- 239000011976 maleic acid Substances 0.000 claims description 2
- -1 maleic acid ester 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 239000002253 acid Substances 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
- 150000002148 esters Chemical class 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
Zusatzpatent zum Hauptpatent Nr. 208950. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen wertvollen Azofarbstoff erhält, wenn man Butyloxäthylaminobenzol, die Diazoverbin- dung des 1-Amino-4-nitrobenzols und Malein- säureanhydrid derart aufeinander einwirken lässt,
dass der saure Haleinsäureester des Bu- tyloxä.thylaminobenzols gebildet wird und der Diazorest in 4-Stellung zur tertiären Amino- gruppe 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 291 Teile des sauren Maleinsäureesters des Butyloxäthylaminobenzols, erhalten durch Umsetzung von Maleinsäureanhydrid mit Bu- thyloxäthylaminobenzol, der in Form einer wässrigen Lösung eines Ammoniumsalzes vor liegt, 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 ge waschen. Man verrührt ihn dann mit einer Natriumchloridlösung und stellt mit Natrium carbonat oder mit Ammoniak auf den Neu tralpunkt.
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 butyloxethylaminobenzene, 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 haloic acid ester of butyloxä.thylaminobenzols is formed and the diazo radical enters in the 4-position to the tertiary amino group.
The dye obtained in this way forms a dark powder which, in the form of an alkali salt, dissolves in water with a red color and dyes acetate rayon from an aqueous solution in red shades.
<I> Example: </I> In the diazo solution, which is produced from 139 parts of 1-amino-4-nitrobenzene, one carries 291 parts of the acidic maleic acid ester of butyloxethylaminobenzene, obtained by reacting maleic anhydride with butyloxäthylaminobenzene, which in In the form of an aqueous solution of an ammonium salt. The coupling is completed by prolonged stirring and neutralizing agents can also be used. such as 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 adjusted to neutral point with sodium carbonate or with ammonia.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211820T | 1937-09-18 | ||
| CH208950T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211820A true CH211820A (en) | 1940-10-15 |
Family
ID=25724611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211820D CH211820A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211820A (en) |
-
1937
- 1937-09-18 CH CH211820D patent/CH211820A/en unknown
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