CH100376A - Process for the preparation of an azo dye. - Google Patents
Process for the preparation of an azo dye.Info
- Publication number
- CH100376A CH100376A CH100376DA CH100376A CH 100376 A CH100376 A CH 100376A CH 100376D A CH100376D A CH 100376DA CH 100376 A CH100376 A CH 100376A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- azo dye
- chloro
- dye
- fastness
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 6
- 150000008049 diazo compounds Chemical class 0.000 claims description 3
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 1
- QZYHIOPPLUPUJF-UHFFFAOYSA-N 3-nitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1 QZYHIOPPLUPUJF-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000007900 aqueous suspension 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
- 238000005530 etching Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Azofarbstoffes. <B>Es</B> wiirde gefunden, dass ein neuer wert- \,oller Azofarbstoff entsteht, wenn man die Diazoverbindung von 5-Chlor-2-toluidin mit 2-3-oxynaphto#s#iure-4-Chlor-o-toluidid kup pelt.
Der Farbstoff kann für sich allein zwechs Verwendung als roter Pigmentfarb stoff hergestellt werden, er kann aber auch auf der vegeta.bilischen Faser erzeugt werden und liefert hierbei einen leuchtend roten klaren Farbton von gegenüber den bekannten Farb stoffen ähnlicher Konstitution hervorragen der Bäucheelitheit, Alkalieclitlieit und Atz- barkeit.
Von sehr grosser Wichtigkeit ist, es, dass hier ein ausgezeichnetes Verwendungsgebiet für das o-Toluidin bezw. o-Nitrofoluol ge funden ist. Bekanntlich entsteht bei der Ni- frierung von Toluol in der Hauptsache o-Ni- Irotoluol,
neben wenig p-INTitrotoluol und ganz geringen Mengen m-Nitrotoluol. Wäli- I t' ZD rend nun für rn-Nitrotol-Liol und besonders p-Nitrotoluol gute Verwendungsmöglichkei t> ten bestanden, musste bisher das o-Nitrotoluol, obwohl es im grössten Prozentsatz zur Ver fügung stand, als lästiges Abfallprodukt be trachtet werden.
<I>Beispiel:</I> Die aus 14,1 gr 5-Clilor-2-tol-tiidin in<B>üb-</B> licher Weise dargestellte Diazoverbinduiig lässt man unter Rühren in eine wässerige Suspension von<B>33</B> gr 2 -3-OxynaphtoCisäure- 4-Clilor-o-toluidid einfliessen, bereitet durch Auflösen in Natronlauge und Wiederausfäl len mit verdünnter Essigsäure. Der Farbstoff scheidet sich in blauroten Flocken aus; darauf wird filtriert, gewaschen und getrocknet.
Process for the preparation of an azo dye. <B> It </B> has been found that a new valuable azo dye is formed if the diazo compound of 5-chloro-2-toluidine is mixed with 2-3-oxynaphto # s # iure-4-chloro-o -toluidid coupling.
The dye can be produced on its own for use as a red pigment dye, but it can also be produced on the vegetable fiber and provides a bright red clear shade with an excellent tummy ity, alkalinity and etching compared to the known dyes of a similar constitution - availability.
It is of very great importance that this is an excellent area of application for o-toluidine respectively. o-nitrofoluene is found. It is well known that when toluene is frozen, o-Ni-irotoluene is the main product,
in addition to a little p-INTitrotoluene and very small amounts of m-nitrotoluene. If there were good uses for rn-nitrotoluene and especially p-nitrotoluene, o-nitrotoluene had to be regarded as an annoying waste product, although the largest percentage of it was available.
<I> Example: </I> The diazo compound prepared from 14.1 g of 5-chloro-2-tol-tiidine in the usual way is left with stirring in an aqueous suspension of <B> 33 </B> gr 2 -3-OxynaphtoCisäure- 4-Clilor-o-toluidid flow in, prepared by dissolving in sodium hydroxide solution and reprecipitating with dilute acetic acid. The dye separates out in blue-red flakes; it is then filtered, washed and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF48892D DE421205C (en) | 1921-03-24 | 1921-03-24 | Process for the production of azo dyes |
| CH99282T | 1922-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH100376A true CH100376A (en) | 1923-07-16 |
Family
ID=25705517
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100375D CH100375A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100374D CH100374A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100378D CH100378A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100377D CH100377A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100372D CH100372A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100376D CH100376A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100373D CH100373A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100375D CH100375A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100374D CH100374A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100378D CH100378A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100377D CH100377A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
| CH100372D CH100372A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH100373D CH100373A (en) | 1921-03-24 | 1922-03-14 | Process for the preparation of an azo dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (7) | CH100375A (en) |
-
1922
- 1922-03-14 CH CH100375D patent/CH100375A/en unknown
- 1922-03-14 CH CH100374D patent/CH100374A/en unknown
- 1922-03-14 CH CH100378D patent/CH100378A/en unknown
- 1922-03-14 CH CH100377D patent/CH100377A/en unknown
- 1922-03-14 CH CH100372D patent/CH100372A/en unknown
- 1922-03-14 CH CH100376D patent/CH100376A/en unknown
- 1922-03-14 CH CH100373D patent/CH100373A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH100373A (en) | 1923-07-16 |
| CH100378A (en) | 1923-07-16 |
| CH100377A (en) | 1923-07-16 |
| CH100375A (en) | 1923-07-16 |
| CH100374A (en) | 1923-07-16 |
| CH100372A (en) | 1923-07-16 |
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