CH211835A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211835A CH211835A CH211835DA CH211835A CH 211835 A CH211835 A CH 211835A CH 211835D A CH211835D A CH 211835DA CH 211835 A CH211835 A CH 211835A
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 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
- 239000000975 dye Substances 0.000 claims description 3
- 239000011976 maleic acid 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
- 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
- 239000003086 colorant Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 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
- 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
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- 101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 description 1
- 101100468762 Caenorhabditis elegans ric-3 gene Proteins 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
- 238000006243 chemical reaction Methods 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
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- FADWLJVAKGATER-UHFFFAOYSA-N n-(2-ethoxyethyl)-2-methoxy-5-methylaniline Chemical compound CCOCCNC1=CC(C)=CC=C1OC FADWLJVAKGATER-UHFFFAOYSA-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-äthyloxäthylamino - benzol, die Diazoverbindung des 1-Amino-2- cyan-4-nitrobenzols und Maleinbsäureanhydrid derart aufeinander einwirken lässt,
dass der saure Maleinsäureester es 5-Methyl-2-me- thoxy-N-äthyloxäthylaminobenzols gebildet wird und der Diazorest in 4-Stellung zur ter tiären Aminogruppe eintritt.
Der so erhaltene Farbstoff bildet ein dunkles Pulver, das sich in Form eines Alkalisalzes in Wasser mit violetter Farbe löst und A.cetatkunstseide aus wässriger Lö sung in violetten Tönen färbt.
<I>Beispiel:</I> In die Diazolösung, die man aus<B>163</B> Tei len 1-Amino-2-,cyan-4-nitrobenzol herstellt, trägt man 307 Teile des sauren Maleinsärure- esters, des 5 - Methyl - 2 - methoxy - N- äthyl - oxäthylaminobenzols, erhalten durch Um setzung von Maleinsäureanhydrid mit 5-Me- thyl-2-methogy - N - äthyloxäthylaminobenzol,
der in Form einer wässrigen Lösung eines Ammoniumsalzess 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-ethyloxethylamino - benzene, the diazo compound of 1-amino-2-cyano-4-nitrobenzene and maleic anhydride, are allowed to act on one another in such a way that
that the acidic maleic acid ester 5-methyl-2-methoxy-N-ethyloxyethylaminobenzene is formed and the diazo radical is in the 4-position to the tertiary amino group.
The dye obtained in this way forms a dark powder, which dissolves in the form of an alkali salt in water with a violet color and colors A. acetate artificial silk from aqueous solution in violet tones.
<I> Example: </I> 307 parts of the acidic maleic acid ester are added to the diazo solution, which is produced from <B> 163 </B> parts of 1-amino-2-, cyano-4-nitrobenzene, des 5 - methyl - 2 - methoxy - N - äthyl - oxäthylaminobenzols, obtained by conversion of maleic anhydride with 5-methyl-2-methoxy - N - äthyloxäthylaminobenzol,
which is in the form of an aqueous solution of an ammonium salt. The coupling is completed by prolonged stirring and, if necessary, neutralizing agents, 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 the neutral point with sodium carbonate or with ammonia.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211835T | 1937-09-18 | ||
| CH208950T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211835A true CH211835A (en) | 1940-10-15 |
Family
ID=25724626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211835D CH211835A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211835A (en) |
-
1937
- 1937-09-18 CH CH211835D patent/CH211835A/en unknown
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