CH132803A - Process for the preparation of a stain dye. - Google Patents
Process for the preparation of a stain dye.Info
- Publication number
- CH132803A CH132803A CH132803DA CH132803A CH 132803 A CH132803 A CH 132803A CH 132803D A CH132803D A CH 132803DA CH 132803 A CH132803 A CH 132803A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- acid
- meta
- water
- brownish
- Prior art date
Links
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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/38—Preparation from compounds with —OH and —COOH adjacent in the same ring or in peri position
- C09B45/40—Chromium compounds
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/06—Disazo dyes from a coupling component "C" containing a directive hydroxyl group
- C09B31/061—Disazo dyes from a coupling component "C" containing a directive hydroxyl group containing acid groups, e.g. -CO2H, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- 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
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
-
- 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
- C09B43/44—Preparation of azo dyes from other azo compounds by substituting amine groups for hydroxyl groups or hydroxyl groups for amine groups; Desacylation of amino-acyl groups; Deaminating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Description
1- Verfahren zur Darstellung eines Beizenfarbstoffes. Im Hauptpatent wurde ein Verfahren be- wonach ein wertvoller Beizen- farbstoff erhalten wird, indem man in p-Ainino- 0-Stilfobenzolazosalicylsä(ire die Aminogruppe diazotiert und mit Saliey1säure kuppelt.
Es wurde nun gefunden, dass ein ähnlicher Farbstoff erhalten wird, wenn man im Mono- , a7 ,ofarbstoff p-Amino-o-sulfoberi7,olazo-i-neta- kresotinsäure die Aminogruppe diazotiert und mit irieta-1Zi-esotinsätire kuppelt.
p-Ainino-o-sulfoberizolazo-meta-kresotiii- säure kann auf verschiedenen Wegen erhalten werden, zum Beispiel: <B>1.</B> -Mionoacetyl-p-phenylendiainiiisulfosäure wird diazotiert und mit meta-Kresotinsäure gekuppelt. Im erhaltenen Azofarbstoff wird die Acetylgruppe durch Verseifen eliminiert und die freie Aminogruppe gebildet.
2. p-Nitraiiilin-o-sulfosäure wird diazotiert und in bekannter Weise mit meta-Kresotin- gäure gekuppelt. Irn erhaltenen Monoazofarb- stoff wird die Nitrogruppe zur Aminogruppe reduziert. <B>3.</B> p-Phonylendiaminsulfosäure wird diazo- tiert und mit ineta-Kresotinsäure gekuppelt.
Der auf die eine oder andere Weise er haltene Körper wird weiter diazotiert und mit nieta-Ki-esotinsäure gekuppelt. Immer wird der gleiche Endfarbstoff erhalten.
Das Verfahren wird erläutert durch folgen des Beispiel: <B>351</B> Teile p-Amino-o-sulfobenzolazo-meta- kresotinsäure werden in Form einer feinen wässerigen Suspension unter Kühlen mit<B>30</B> Teilen Salzsäure versetzt und durch langsames Zugeben von<B>7</B> Teilen Natriumnitrit diazotiert. Der<B>-</B>schwer lösliche rotbraun gefärbte Diazo- körper wird abfiltriert und in feuchtem Zu stande allmählich bei<B>0-5'</B> C in eine Mi schung von<B>170</B> Teilen meta-Kresotinsäure, <B>1000</B> Teilen Wasser,
40 Teilen Ätznatron und<B>500</B> Teilen Magnesiumkarbonat einge rührt. Die Kupplungsmasse, die zu Anfang eine braunschwarze Färbung zeigt, wird nach einiger Zeit gelbbraun. Nach beendigter<B>Kupp-</B> lung wird die Masse angesäuert und filtriert. Der so ausgeschiedene Farbstoff wird in Wasser und Borax heiss gelöst, filtriert, even tuell nochmals sauer abgeschieden Lind her nach wieder in Wasser und Borax gelöRt und mit Kochsalz ausgesalzen.
In diesem Beispiel kann die Kupplung mit auch Hilfe von Soda oder Natronlatige durchgeführt werden.
In Wasser löst sich der neue Farbstoff mit braungelber Farbe, die auf Zusatz von Natronlauge nach rotviolett umschlägt. In konzentrierter Schwefelsäure löst er sich init blauer Farbe. Durch Verdünnen dieser Lö sung mit Wasser wird er als dunkelbraune Flocken gefällt.
Der neue Farbstoff färbt ehromierte Wolle in braunstichig orangen Tönen an. Mit Chrom beize auf Baumwolle gedruckt gibt er kräftige braunstichig orange Nuancen, die rotstichis ger sind als diejenigen des Farbstoffes de- Hauptpatentes und gute Echtheitseigenschaf ten aufweisen.
1- Process for the preparation of a stain dye. The main patent describes a process whereby a valuable mordant dye is obtained by diazotizing the amino group in p-amino-0-stilfobenzolazosalicylic acid and coupling it with salyic acid.
It has now been found that a similar dye is obtained if the amino group in the mono-, a7, o-dye is diazotized with p-amino-o-sulfoberi7, olazo-i-netakresotinic acid and coupled with irieta-1Zi-esotinsätire.
p-Ainino-o-sulfoberizolazo-meta-cresotinic acid can be obtained in various ways, for example: 1. -Mionoacetyl-p-phenylenediamine-sulfonic acid is diazotized and coupled with meta-cresotinic acid. In the azo dye obtained, the acetyl group is eliminated by saponification and the free amino group is formed.
2. p-nitrilin-o-sulfonic acid is diazotized and coupled with meta-cresotinic acid in a known manner. In the monoazo dye obtained, the nitro group is reduced to the amino group. <B> 3. </B> p-Phonylenediaminesulfonic acid is diazo- tated and coupled with ineta-cresotinic acid.
The body retained in one way or another is further diazotized and coupled with nieta-ki-esotinic acid. The same final dye is always obtained.
The process is illustrated by the following example: <B> 351 </B> parts of p-amino-o-sulfobenzolazo-metacresotinic acid are mixed with <B> 30 </B> parts of hydrochloric acid in the form of a fine aqueous suspension while cooling and diazotized by slowly adding <B> 7 </B> parts of sodium nitrite. The <B> - </B> poorly soluble, red-brown colored diazo body is filtered off and, in the moist state, gradually at <B> 0-5 '</B> C into a mixture of <B> 170 </B> Parts meta-cresotinic acid, <B> 1000 </B> parts of water,
40 parts of caustic soda and <B> 500 </B> parts of magnesium carbonate are stirred in. The coupling compound, which initially shows a brown-black color, turns yellow-brown after a while. After the <B> coupling </B> process is complete, the mass is acidified and filtered. The dyestuff separated out in this way is dissolved in hot water and borax, filtered, possibly again separated in acidic form and then redissolved in water and borax and salted out with common salt.
In this example the coupling can also be carried out with the help of soda or soda soda.
The new dye dissolves in water with a brownish-yellow color, which changes to red-violet when caustic soda is added. In concentrated sulfuric acid it dissolves in a blue color. By diluting this solution with water, it is precipitated as dark brown flakes.
The new dye dyes honored wool in brownish orange tones. Printed with chrome stain on cotton, it gives strong brownish orange nuances, which are more reddish than those of the dye of the main patent and have good fastness properties.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH132803T | 1928-01-12 | ||
| CH123930T | 1928-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH132803A true CH132803A (en) | 1929-04-30 |
Family
ID=25710165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132803D CH132803A (en) | 1928-01-12 | 1928-01-12 | Process for the preparation of a stain dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH132803A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158888A3 (en) * | 1984-04-05 | 1987-02-04 | Hoechst Aktiengesellschaft | Disazo compounds, process for their preparation and their use |
-
1928
- 1928-01-12 CH CH132803D patent/CH132803A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0158888A3 (en) * | 1984-04-05 | 1987-02-04 | Hoechst Aktiengesellschaft | Disazo compounds, process for their preparation and their use |
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