CH198332A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH198332A CH198332A CH198332DA CH198332A CH 198332 A CH198332 A CH 198332A CH 198332D A CH198332D A CH 198332DA CH 198332 A CH198332 A CH 198332A
- Authority
- CH
- Switzerland
- Prior art keywords
- yellow
- greenish
- azo dye
- preparation
- acid
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 2
- RIERSGULWXEJKL-UHFFFAOYSA-N 3-hydroxy-2-methylbenzoic acid Chemical compound CC1=C(O)C=CC=C1C(O)=O RIERSGULWXEJKL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 triphenyl ethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. <B>196661.</B> Verfahren zur IffersteUung eines Azofarbstoffes. Es wurde gefunden, dass Diazoverbin- dungen, die sich von Aminodi- und triphenyl- äthern ableiten und die wasserlöslich machende Gruppen, aber keine Nitrogruppen enthalten, beim Kuppeln mit hydroaromatischen, carbo- cyclischen P-Diketonen hervorragend reine gelbe Woll- und Seidenfarbstoffe ergeben,
die neben guter Wasch- und Schweissechtheit sich auch durch sehr gute Lichtechtheit auszeichnen. Sie können auch zur Herstellung von Lacken durch Fällung mit Erdalkli- salzen dienen.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines gelben Azofarbstoffes, das darin besteht, dass man diazotierte 4-Amino-2'-niethyl-1,1'-diphenyl- äther-3-sulfotisäure der Formel
EMI0001.0021
mit Dimethyldihydroresorein kuppelt. Der neue Farbstoff, ein grünlich gelbes Pulver, löst sich<U>in</U> Wasser mit grünlich gelber, in konzentrierter Schwefelsäure mit orangegelber Farbe und färbt Wolle und Seide in saurem Bade in sehr reiner), grünlich gelben, sehr lichtechten Tönen.
<I>Beispiel:</I> <B>28 kg</B> 4-Amino-2'-metb.y1-1,1'-diphenyl- äthei--3-sulfonsäLire werden wie üblich diazo- Liert und die Diazoverbindung bei<B>00 C</B> in eine Auflösung von 14,5<B>kg</B> Dimethyldibydro- resorein in 400 Liter Wasser und<B>10</B> Liter Natronlauge<B>29,7</B> '/o, die man nach Zugabe von 20<B>kg</B> kristallisiertem Natriumacetat mit wenig verdünnter Essigsäure lackmussauer gestellt hat, einlaufen gelassen. Die Kupp lung verläuft sehr schnell.
Nach mehrstün digem Rühren scheidet sich der grünlich gelbe Farbstoff quantitativ aus. Er wird filtriert und getrocknet. Er stellt ein grünlich gelbes Pulver dar, das sich in Wasser mit grünlich gelber und in konzentrierter Schwefelsäure mit. orangegelber Farbe löst und Wolle und Seide in saurem Bade in sehr reinen grünlich gelben, sehr lichtechten Tönen anfärbt.
Die 4-Amino-2'-methyl-1, l'-diphenylätlier- 3-sulfonsäure wird in üblicher Weise durch Umsetzun-, von o-Kresolat mit 4-Nitrochlor- benzol-3-sulfoi#sätii-e und nachfolgende Reduk tion erhalten.
Additional patent to main patent no. <B> 196661. </B> Process for controlling an azo dye. It has been found that diazo compounds which are derived from aminodi- and triphenyl ethers and which contain water-solubilizing groups but no nitro groups, when coupled with hydroaromatic, carbocyclic P-diketones, give excellent pure yellow wool and silk dyes,
which, in addition to good fastness to washing and perspiration, are also characterized by very good fastness to light. They can also be used to produce paints by precipitation with alkaline earth salts.
The present patent relates to a process for the preparation of a yellow azo dye, which consists in that diazotized 4-amino-2'-niethyl-1,1'-diphenyl ether-3-sulphotic acid of the formula
EMI0001.0021
coupled with dimethyldihydroresorein. The new dye, a greenish yellow powder, dissolves <U> in </U> water with greenish yellow, in concentrated sulfuric acid with orange-yellow color and dyes wool and silk in an acid bath in very pure), greenish yellow, very lightfast shades.
<I> Example: </I> <B> 28 kg </B> 4-Amino-2'-metb.y1-1,1'-diphenyl ether - 3-sulfonic acids are diazo-lated as usual and the Diazo compound at <B> 00 C </B> in a resolution of 14.5 <B> kg </B> dimethyldibydro- resorein in 400 liters of water and <B> 10 </B> liters of sodium hydroxide <B> 29.7 </B> '/ o, which was poured in after adding 20 <B> kg </B> crystallized sodium acetate with a little dilute acetic acid. The coupling is very quick.
After several hours of stirring, the greenish yellow dye separates out quantitatively. It is filtered and dried. It is a greenish-yellow powder that dissolves in water with greenish-yellow and in concentrated sulfuric acid. orange-yellow color dissolves and dyes wool and silk in an acidic bath in very pure greenish-yellow, very lightfast shades.
The 4-amino-2'-methyl-1, l'-diphenylethyl-3-sulfonic acid is sätii-e in the usual way by reaction, of o-cresolate with 4-nitrochlorobenzene-3-sulfo # s and subsequent reduction receive.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH196651T | 1937-03-19 | ||
| CH198332T | 1937-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH198332A true CH198332A (en) | 1938-06-15 |
Family
ID=25722873
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH198332D CH198332A (en) | 1937-03-19 | 1937-03-19 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH198332A (en) |
-
1937
- 1937-03-19 CH CH198332D patent/CH198332A/en unknown
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