CH211803A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211803A CH211803A CH211803DA CH211803A CH 211803 A CH211803 A CH 211803A CH 211803D A CH211803D A CH 211803DA CH 211803 A CH211803 A CH 211803A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- methyl
- preparation
- dye
- diazo
- 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
- GHTWWZFQIYPDCX-UHFFFAOYSA-N N-ethoxy-N-ethyl-3-methylaniline Chemical compound CCON(CC)C1=CC=CC(C)=C1 GHTWWZFQIYPDCX-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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 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
- 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
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002955 Art silk 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
- 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
- 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)
- Detergent Compositions (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>208950.</B> Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen wertvollen Azofarbstoff erhält, wenn man 5-Met'hyl-N-ätllyloxyät'hylaminobenzol, die Diazoverbindung des 1-Amino-4-nitrobenzol- 2-metliylsulions undMaleinsäureanllydrid der art aufeinander einwirken lässt,
dass der saure Maleinsäureester des 5-Methyl-N-ät'hyloxy- ät'hylaminobenzols gebildet wird und der Di- azorest in 4-Stellung zur tertiären Amino- gruppe eintritt.
Der so erhaltene Farbstoff bildet ein dunkles Pulver, das sieh in Form eines Al- kalisalzes in Wasser mit violetter Farbe löst und Acetatkunstseide auf wässeriger Lösung in violetten Tönen färbt.
<I>Beispiel:</I> In die Diazolösung, die man aus<B>216</B> Tei len 1-Amino-4-nitrobenzol-2-methylsulfon herstellt, trägt man<B>277</B> Teile des sauren Maleinsäureesters des 5-Methyl-N-äthyloxy- äthylaminobenzols, erhalten durch Umset- zung von Maleinsäureanhydrid mit 5-Me- thyl-N-ätliyloxyä,t'hylaminobenzol, der in Form einer wässerigen Lösung seines Ammo- uiumsalzes vorliegt<B>,</B> 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 Natriumehloridlösung und stellt mit Natriumearbonat oder mit Ammoniak auf den Neutralpunkt.
Additional patent to main patent no. <B> 208950. </B> Process for the production of an azo dye. It has been found that a new valuable azo dye is obtained if 5-methyl-N-ätllyloxyät'hylaminobenzene, the diazo compound of 1-amino-4-nitrobenzene-2-methylsulion and maleic anhydride, is allowed to act on one another
that the acidic maleic acid ester of 5-methyl-N-ät'hyloxy-ät'hylaminobenzols is formed and the diazo group occurs 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 violet color and dyes acetate artificial silk on an aqueous solution in violet shades.
<I> Example: </I> <B> 277 </B> parts are added to the diazo solution that is produced from <B> 216 </B> parts of 1-amino-4-nitrobenzene-2-methylsulfone of the acidic maleic acid ester of 5-methyl-N-ethyloxy-ethylaminobenzene, obtained by reacting maleic anhydride with 5-methyl-N-ethyloxy-ethylaminobenzene, which is in the form of an aqueous solution of its ammonium salt <B> , </B> a.
The coupling is completed by prolonged stirring and neutralizing agents can also be used. 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 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 | ||
| CH211803T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211803A true CH211803A (en) | 1940-10-15 |
Family
ID=25724594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211803D CH211803A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211803A (en) |
-
1937
- 1937-09-18 CH CH211803D patent/CH211803A/en unknown
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