CH211806A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211806A CH211806A CH211806DA CH211806A CH 211806 A CH211806 A CH 211806A CH 211806D A CH211806D A CH 211806DA CH 211806 A CH211806 A CH 211806A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- dye
- methyloxyethylaminobenzene
- preparation
- 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 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-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
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- XTTMNDFFWSZHCZ-UHFFFAOYSA-N n-(2-methoxyethyl)aniline Chemical compound COCCNC1=CC=CC=C1 XTTMNDFFWSZHCZ-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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 2
- -1 phthalic acid ester Chemical class 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 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
- 239000003795 chemical substances by application Substances 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
- C09B43/22—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 having the carboxylic group directly attached to an aromatic carbocyclic ring
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 Methyloxyäthylaminobenzol, die Diazover- bindung des 1 - Amino - 4 - nitrobenzols und Phthalsäureanhydrid derart aufeinander ein wirken lässt,
dass der saure Phthalsäureester des i4ethyloxyäthylaminobenzols 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 Al kalisalzes in W asser mit roter Farbe löst und Acetatkunstseide aus wässeriger Lösung in scharlachroten Tönen färbt.
<I>Beispiel:</I> In die Diazolösung, die man aus 139 Tei len 1-Amino-4-nitrobenzol herstellt, trägt man 299 Teile des sauren Phthalsäureesters des 2llethyloxyäthylaminobenzols, erhalten durch Umsetzung von Phthalsäureanhydrid tnit 3Tethyloxyäthylaminobenzol, der in Form einer wässerigen Lösung eines Ammonium- en 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.
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 methyloxyethylaminobenzene, the diazo compound of 1 - amino - 4 - nitrobenzene and phthalic anhydride, can act on one another in such a way that
that the acidic phthalic ester of i4ethyloxyäthylaminobenzols is formed and the diazo radical occurs in the 4-position to the tertiary amino group.
The thus obtained. The dye forms a dark powder that dissolves in the form of an alkali salt in water with a red color and dyes acetate artificial silk from an aqueous solution in scarlet shades.
<I> Example: </I> In the diazo solution, which is produced from 139 parts of 1-amino-4-nitrobenzene, you carry 299 parts of the acidic phthalic acid ester of 2llethyloxyäthylaminobenzols, obtained by reacting phthalic anhydride with 3-thyloxyethylaminobenzene, which is in the form of a aqueous solution of an ammonium is present. You lead the hitch ment by prolonged stirring to the end 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 |
|---|---|---|---|
| CH211806T | 1937-09-18 | ||
| CH208950T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211806A true CH211806A (en) | 1940-10-15 |
Family
ID=25724597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211806D CH211806A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211806A (en) |
-
1937
- 1937-09-18 CH CH211806D patent/CH211806A/en unknown
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