CH306548A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH306548A CH306548A CH306548DA CH306548A CH 306548 A CH306548 A CH 306548A CH 306548D A CH306548D A CH 306548DA CH 306548 A CH306548 A CH 306548A
- Authority
- CH
- Switzerland
- Prior art keywords
- thianthrene
- dicarboxylic acid
- amino
- acid residue
- production
- 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 claims description 3
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- FLJUGDGSJUTBJZ-UHFFFAOYSA-N thianthrene-1,2-dicarboxylic acid Chemical class C1=CC=C2SC3=C(C(O)=O)C(C(=O)O)=CC=C3SC2=C1 FLJUGDGSJUTBJZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- LJIXESAWMWZFLV-UHFFFAOYSA-N 1,2-dibromothianthrene Chemical compound C1=CC=C2SC3=C(Br)C(Br)=CC=C3SC2=C1 LJIXESAWMWZFLV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- WLWJCSOHYTYVMH-UHFFFAOYSA-N N-(5-amino-9,10-dioxoanthracen-1-yl)-4-chloro-2-fluorobenzamide Chemical compound NC1=C2C(=O)C3=C(C(NC(=O)C4=C(F)C=C(Cl)C=C4)=CC=C3)C(=O)C2=CC=C1 WLWJCSOHYTYVMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 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
- 239000012442 inert solvent Substances 0.000 claims description 2
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- -1 thianthrene dicarboxylic acid halide Chemical class 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 3
- 239000000203 mixture 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 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
- C09B1/44—Dyes with acylated amino groups the acyl groups being residues of a heterocyclic carboxylic acid
- C09B1/445—Dyes with acylated amino groups the acyl groups being residues of a heterocyclic carboxylic acid dicarboxylic
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-4'-chlorbenzoyl- i amino) -anthraehinon mit einem Mol eines Thianthrendiearbonsäurederivates umsetzt, welches den Thianthrendicorbonsäurerest ab- ;
gibt, der der derjenigen Thianthrendicarbonsäure entspricht, in welcher die Carbonsäuregrup- pen dieselbe Stellung einnehmen wie die Bromatome des durch Dibromierung von Thianthren in Nitrobenzol erhältlichen Di- bromthianthrens.
Der neue Farbstoff färbt Baumwolle aus der Hydrosulfitküpe in echten gelben Tönen. Als Mittel, welche den Thian.threndicar- bonsäurerest abgeben, kommen z. B. funktio nelle Derivate der oben genannten Säure, insbesondere die Halogenide dieser Säure und unter diesen vor allem das Dichlorid, in Be tracht.
Die Umsetzung des 1-Amino-5-(2'-fluor-4'- chlorbenzoyIamino)-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 Tempe- ratur, z. B. beim Siedepunkt der betreffen den Lösungsmittel, durch.
<I>Beispiel:</I> Eine Mischung von 1,12 Teilen Thianthren- dicarbonsäure der gleichen Zusammensetzung, wie sie in der englischen Patentschrift 555055 Verwendung findet, 6 Teilen Thionylchlorid, 90 Teilen Trichlorbenzol und 0,05 Teil Pyri- din wird 30 Minuten lang bei 80 und 30 Minuten bei 120 gerührt. Man erhitzt hier auf zum Sieden, wobei das überschüssige Thionylchlorid und etwas Trichlorbenzol ab destillieren.
Man lässt die Lösung auf 100 abkühlen, setzt der Lösung 3 Teile 1-Amino- 5- (2'-fluor-4'-chlorbenzoylamino)-anthrachinon zu, und erhitzt 2 Stunden auf 200 bis 210 . Der entstandene Farbstoff wird dann bei etwa 120 abfiltriert und wie üblich aufge arbeitet.
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-4'-chlorobenzoyl- i amino) -anthraehinone are reacted with one mole of a thianthrenic dicarboxylic acid derivative which removes the thianthrendicorbonic acid residue;
which corresponds to that of the thianthrene dicarboxylic acid in which the carboxylic acid groups occupy the same position as the bromine atoms of the dibromothianthrene obtainable by dibromination of thianthrene in nitrobenzene.
The new dye dyes cotton from the hydrosulfite vat in real yellow tones. As agents which release the Thian.threndicar- bonsäurerest, z. B. func tional derivatives of the above acid, especially the halides of this acid and, among these, especially the dichloride, in Be tracht.
The reaction of the 1-amino-5- (2'-fluoro-4'-chlorobenzoyiamino) -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 goes easily at elevated tempera ture, one advantageously chooses those solvents that have a relatively high boiling point, such as chlorobenzene, o-dichlorobenzene, trichlorobenzene, nitrobenzene or naphthalene, and leads the reaction completely or at least to .
Part at high temperature, e.g. B. at the boiling point of the concern the solvent by.
<I> Example: </I> A mixture of 1.12 parts of thianthrene dicarboxylic acid of the same composition as used in English patent specification 555055, 6 parts of thionyl chloride, 90 parts of trichlorobenzene and 0.05 part of pyridine is 30 Stirred for 80 minutes and 120 for 30 minutes. It is heated to the boil here, the excess thionyl chloride and some trichlorobenzene distilling off.
The solution is allowed to cool to 100, 3 parts of 1-amino-5- (2'-fluoro-4'-chlorobenzoylamino) anthraquinone are added to the solution, and the mixture is heated to 200 to 210 for 2 hours. The resulting dye is then filtered off at about 120 and worked up as usual.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306548T | 1951-10-30 | ||
| CH275439T | 1951-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306548A true CH306548A (en) | 1955-04-15 |
Family
ID=25731618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306548D CH306548A (en) | 1951-10-30 | 1951-10-30 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306548A (en) |
-
1951
- 1951-10-30 CH CH306548D patent/CH306548A/en unknown
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