CH211807A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH211807A CH211807A CH211807DA CH211807A CH 211807 A CH211807 A CH 211807A CH 211807D A CH211807D A CH 211807DA CH 211807 A CH211807 A CH 211807A
- Authority
- CH
- Switzerland
- Prior art keywords
- azo dye
- yellow
- dye
- 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
- -1 phthalic acid ester Chemical class 0.000 claims description 4
- 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-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
- 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
- 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
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-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
- C09B43/22—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
<B>Zusatzpatent</B> zum hauptpatent Nr. 208950. Verfahren zur Herstellung eines Azofarbstoffes. Es wurde gefunden, dass man einen neuen wertvollen Azofarbstoff erhält, wenn man Äthyloxäthylaminobenzol, die Diazoverbin- dung des 1-Amir)o-3-nitro-6-methoxybenzols und Phthalsäureanhydrid derart aufeinander einwirken lässt,
dass der saure Phthalsäure- ester des 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 Alkali salzes in Wasser mit gelboranger Farbe löst und Acetatkunstseide aus wässeriger Lösung in gelborangen Tönen färbt.
<I>Beispiel:</I> In die Diazolösung, die man aus 168 Teilen 1-Amino-3-nitro-6-methoxybenzol herstellt, trägt man 313 Teile des sauren Phthalsäure- esters des Äthyloxäthylaminobenzols, erhalten durch Umsetzung von Phthalsäureanhydrid mit Äthyloxäthylaminobenzol, der in Form einer wässerigen Lösung seines Ammonium salzes 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-Natrium- carbonat oder mit Ammoniak auf den Neutral punkt.
<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 ethyloxethylaminobenzene, the diazo compound of 1-amir) o-3-nitro-6-methoxybenzene and phthalic anhydride are allowed to act on one another in such a way that
that the acidic phthalic acid ester of Äthyloxäthylaminobenzols is formed and the diazo radical occurs 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 yellow-orange color and dyes acetate rayon from an aqueous solution in yellow-orange shades.
<I> Example: </I> 313 parts of the acidic phthalic acid ester of ethyloxethylaminobenzene, obtained by reacting phthalic anhydride with ethyloxethylaminobenzene, are added to the diazo solution, which is prepared from 168 parts of 1-amino-3-nitro-6-methoxybenzene , which is in the form of an aqueous solution of its 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 set to neutral with sodium carbonate or ammonia.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH211807T | 1937-09-18 | ||
| CH208950T | 1937-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH211807A true CH211807A (en) | 1940-10-15 |
Family
ID=25724598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH211807D CH211807A (en) | 1937-09-18 | 1937-09-18 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH211807A (en) |
-
1937
- 1937-09-18 CH CH211807D patent/CH211807A/en unknown
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