CH308793A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH308793A CH308793A CH308793DA CH308793A CH 308793 A CH308793 A CH 308793A CH 308793D A CH308793D A CH 308793DA CH 308793 A CH308793 A CH 308793A
- Authority
- CH
- Switzerland
- Prior art keywords
- azobenzenedicarboxylic acid
- agent
- amino
- azobenzenedicarboxylic
- vat
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000975 dye Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- ZQKYATCNQQKPQS-UHFFFAOYSA-N NC1=CC=CC(C(C(C2=CC=C3)=C3NC(C(C=C(C=C3)Cl)=C3F)=O)=O)=C1C2=O Chemical compound NC1=CC=CC(C(C(C2=CC=C3)=C3NC(C(C=C(C=C3)Cl)=C3F)=O)=O)=C1C2=O ZQKYATCNQQKPQS-UHFFFAOYSA-N 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/32—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines
- C09B43/36—Preparation of azo dyes from other azo compounds by reacting carboxylic or sulfonic groups, or derivatives thereof, with amines; by reacting keto-groups with amines with amino-anthracene or amino-anthraquinone dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 275439. Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Küpenfarbstoff gelangt, wenn man zwei Mol 1-Amino-5- (2'-fluor-5'-chlorbenzoyl- amino)-anthra.chinon mit einem Mol eines den Rest der 3,3'-Azobenzoldicarbonsäure abgeben den Mittels umsetzt.
Der neue Farbstoff färbt Baumwolle aus bordeauxroter Hydrosulfitküpe in vollgelben Tönen von hervorragender Lichtechtheit.
Als Mittel, welche den 3,3'-Azobenzoldicar- bonsäurerest abgeben, kommen z. B. funktio nelle Derivate der oben genannten Säure, ins besondere die Halogenide dieser Säure und un ter diesen vor allem das Dichlorid, in Betracht.
Die Umsetzung des 1-Amino-5-(2'-fluor-5'- clilorbenzoylamino) -anthrachinons mit dem Acylierungsmittel kann nach allgemein be kannten Methoden vorgenommen werden. Zweckmässig lässt man die Ausgangsstoffe, in einem indifferenten Lösungs- bzw. Vertei lungsmittel miteinander reagieren.
Da die Reaktion in der Regel bei erhöhter Tempera tur leicht vor sich geht, wählt man vorteil haft. solche Lösungsmittel, die einen relativ hohen Siedepunkt besitzen, wie Chlorbenzol, o-Dichlorbenzol, Trichlorbenzol, Nitrobenzol oder Naphthalin, und führt die Reaktion ganz oder mindestens zum Teil bei hoher Temperatur, z. B. beim Siedepunkt der betreffenden Lösungs mittel, durch.
<I>Beispiel:</I> Eine Mischung von 0,9 Teilen 3,3'-Azoben- zoldicarbonsäure, 6 Volumteilen Thionylchlo- rid, 90 Volumteilen Trichlorbenzol und 0,05 Teilen Pyridin wird 30 Minuten bei 80 und 30 Minuten bei 120 gerührt und dann zum Sieden erhitzt, wobei das Thionylchlorid und etwas Triehlorbenzol abdestilliert wird.
Man lässt die Lösung auf 100 abkühlen und setzt der Lösung 3 Teile 1-Amino-5-(2'-fluor-5'- chlorbenzoylamino)-anthra,chinon zu und er hitzt 2 Stunden auf 200 bis 210 . Nach dem Abkühlen auf etwa 120 wird der Farbstoff abfiltriert und wie üblich aufgearbeitet.
Additional patent to main patent No. 275439. Process for the production of a vat dye. It has been found that a valuable vat dye is obtained if two moles of 1-amino-5- (2'-fluoro-5'-chlorobenzoyl-amino) -anthraquinone are mixed with one mole of the remainder of the 3,3 ' -Azobenzenedicarboxylic acid release the agent.
The new dye dyes cotton from a burgundy hydrosulfite vat in full yellow tones with excellent lightfastness.
As agents which release the 3,3'-azobenzenedicarboxylic acid residue, z. B. func tional derivatives of the above acid, in particular the halides of this acid and under these especially the dichloride, into consideration.
The reaction of the 1-amino-5- (2'-fluoro-5'-clilorbenzoylamino) -anthraquinone with the acylating agent can be carried out according to generally known methods. The starting materials are expediently allowed to react with one another in an inert solvent or distributing agent.
Since the reaction usually takes place easily at elevated temperatures, it is advantageous to choose. those solvents which have a relatively high boiling point, such as chlorobenzene, o-dichlorobenzene, trichlorobenzene, nitrobenzene or naphthalene, and carry out the reaction wholly or at least in part at high temperature, e.g. B. at the boiling point of the relevant solvent medium, through.
<I> Example: </I> A mixture of 0.9 parts of 3,3'-azobenzene dicarboxylic acid, 6 parts by volume of thionyl chloride, 90 parts by volume of trichlorobenzene and 0.05 part of pyridine is heated for 30 minutes at 80 and 30 minutes at 120 stirred and then heated to the boil, the thionyl chloride and a little triehlobenzene being distilled off.
The solution is allowed to cool to 100 and 3 parts of 1-amino-5- (2'-fluoro-5'-chlorobenzoylamino) -anthra, quinone are added to the solution and it is heated to 200-210 for 2 hours. After cooling to about 120, the dye is filtered off and worked up as usual.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308793T | 1951-10-30 | ||
| CH275439T | 1951-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308793A true CH308793A (en) | 1955-07-31 |
Family
ID=25731623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308793D CH308793A (en) | 1951-10-30 | 1951-10-30 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308793A (en) |
-
1951
- 1951-10-30 CH CH308793D patent/CH308793A/en unknown
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