CH283764A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH283764A CH283764A CH283764DA CH283764A CH 283764 A CH283764 A CH 283764A CH 283764D A CH283764D A CH 283764DA CH 283764 A CH283764 A CH 283764A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- remainder
- production
- agent
- dicarboxylic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000000984 vat dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- MRCLOZRVAKCPQU-UHFFFAOYSA-N 1,4-diamino-2-(4-chlorobenzoyl)anthracene-9,10-dione Chemical compound NC=1C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=1C(=O)C1=CC=C(Cl)C=C1 MRCLOZRVAKCPQU-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000011230 binding agent Substances 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
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-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
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RGSSNRUMBGOYSB-UHFFFAOYSA-N 1,4-dichloro-9,10-dioxoanthracene-2-carbonyl chloride Chemical compound ClC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)Cl)C(=O)Cl RGSSNRUMBGOYSB-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940052651 anticholinergic tertiary amines Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000004820 halides Chemical class 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
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
- C09B1/43—Dicarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Küpenfarbstoff gelangt, wenn man zwei Mol 1,4-Diamino-2- (p-ehlorbenzoyl)- anthraehinon mit einem lTol eines den Rest der Formel
EMI0001.0009
abgebenden Mittels umsetzt.
Der neue Farbstoff färbt Baumwolle aus der Hydrosulfitküpe in echten, rotstiehig blauen Tönen.
Als Mittel, welche den Rest der obigen Formel abgeben, kommen z. B. funktionelle Derivate der Diphenyl-4,4'-dicarbonsäure, ins besondere die Halogenide dieser Säure und unter diesen vor allem das Diphenyl-4,4'-di- carbonsäuredichlorid in Betracht.
Die Umsetzung des 1,4-Diamino-2-(p-chlor- benzoyl)-anthrachinons mit dem Acylierungs- mittel kann nach allgemein bekannten Me thoden vorgenommen werden. Zweckmässig lässt man die Ausgangsstoffe in einem indif- ferenten Lösungs- bzw. Verteilungsmittel mit einander reagieren.
Da die Reaktion in der Regel bei erhöhter Temperatur leicht vor sich geht, wählt man vorteilhaft solche Lösungs mittel, die einen relativ hohen Siedepunkt be sitzen, wie Chlorbenzol, o-Dichlorbenzol, Ni- trobenzol oder Naphthalin und führt die Re aktion ganz oder mindestens zum Teil bei hoher Temperatur, z. B. beim Siedepunkt der betreffenden Lösungsmittel, durch, wobei in bekannter Weise säurebindende Mittel wie ter tiäre Amine, z. B. Pyridin oder Chinolin, bei der Reaktion mitverwendet werden können.
<I>Beispiel:</I> Eine Mischung von 2,7 Teilen Diphenyl- 4,4'-dicarbonsäuredichlorid, 8 Teilen 1,4-Di- amino-2-(p-ehlorbenzoyl)-anthrachinon, 5 Tei len Pvridin und 225 Teilen Trichlorbenzol wird unter Rühren und stetigem Steigern der Temperatur in 3 Stunden auf 160 erhitzt.
Man rührt noch eine halbe Stunde lang und filtriert alsdann den Farbstoff der Formel
EMI0001.0034
Das 1,4-Diamino-2-(p-chlorbenzoyl)-anthra- chinon kann hergestellt werden, indem man 1,4-Dichloranthrachinon-2-carbonsäureehlorid nach Friedel-Craffts mit Chlorbenzol konden siert und hierauf die im Anthrachinonkern vorhandenen beiden Chloratome in Amino- gruppen umwandelt.
Process for the production of a vat dye. It has been found that a valuable vat dye is obtained if two moles of 1,4-diamino-2- (p-chlorobenzoyl) -anthraehinone are mixed with one tol of the remainder of the formula
EMI0001.0009
releasing agent implements.
The new dye dyes cotton from the hydrosulfite vat in real, reddish blue tones.
As agents which deliver the remainder of the above formula, z. B. functional derivatives of diphenyl-4,4'-dicarboxylic acid, in particular the halides of this acid and, among these, especially diphenyl-4,4'-dicarboxylic acid dichloride.
The conversion of the 1,4-diamino-2- (p-chlorobenzoyl) anthraquinone with the acylating agent can be carried out by generally known methods. The starting materials are expediently allowed to react with one another in an indifferent solvent or distribution medium.
Since the reaction usually goes easily at elevated temperature, it is advantageous to choose those solvents that have a relatively high boiling point, such as chlorobenzene, o-dichlorobenzene, nitrobenzene or naphthalene, and lead the reaction completely or at least to Part at high temperature, e.g. B. at the boiling point of the solvent concerned, by, in a known manner acid-binding agents such as ter tiary amines, z. B. pyridine or quinoline, can be used in the reaction.
<I> Example: </I> A mixture of 2.7 parts of diphenyl-4,4'-dicarboxylic acid dichloride, 8 parts of 1,4-di-amino-2- (p-chlorobenzoyl) -anthraquinone, 5 parts of pvridine and 225 parts of trichlorobenzene are heated to 160 over the course of 3 hours, while stirring and continuously increasing the temperature.
The mixture is stirred for a further half an hour and then filtered the dye of the formula
EMI0001.0034
The 1,4-diamino-2- (p-chlorobenzoyl) anthraquinone can be prepared by condensing 1,4-dichloroanthraquinone-2-carboxylic acid chloride according to Friedel-Craffts with chlorobenzene and then converting the two chlorine atoms present in the anthraquinone nucleus into Converts amino groups.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH283764T | 1949-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH283764A true CH283764A (en) | 1952-06-30 |
Family
ID=4484223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH283764D CH283764A (en) | 1949-07-22 | 1949-07-22 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH283764A (en) |
-
1949
- 1949-07-22 CH CH283764D patent/CH283764A/en unknown
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