CH181719A - Process for the production of a new dye of the anthraquinone series. - Google Patents
Process for the production of a new dye of the anthraquinone series.Info
- Publication number
- CH181719A CH181719A CH181719DA CH181719A CH 181719 A CH181719 A CH 181719A CH 181719D A CH181719D A CH 181719DA CH 181719 A CH181719 A CH 181719A
- Authority
- CH
- Switzerland
- Prior art keywords
- mol
- amino
- new dye
- production
- sulfonic acid
- Prior art date
Links
- 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 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229920000297 Rayon Polymers 0.000 claims description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 4
- 241000974482 Aricia saepiolus Species 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000002964 rayon Substances 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000725 suspension 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
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- C09B1/467—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound attached to two or more anthraquinone rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines neuen Farbstoffes der Anthraehinonreihe. Es wurde gefunden, dass man einen neuen Farbstof<B>f</B> der Anthrachinonreihe erhält, wenn man auf 1 Mol Cyanurchlorid 1 Mol 1 Amino-4-(4'-amino)-anilidoanthrachinon-2- sulfonsäure, 1.
Mol 2-Amino-5-oxynaphthalin- 7-sulfonsä.ure und 1 Mol Anilin derart ein wirken lässt, dass je ein Halogenatom des Cyanurchlorides durch je 1 Mol der drei wei teren Ausgangsstoffe ausgetauscht wird.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blauer Farbe löst, und Baumwolle, Viskosekunstseide, Wolle oder Seide in grünstichig-blauen Tönen von guter Lichtechtheit färbt.
Beispiel: 18,5 Teile Cyanurchlorid werden in 800 'feilen Wasser fein suspendiert. Zu dieser Suspension giesst man eine neutrale Lösung von 40,8 Teilen 1-Amino-4-(4'-amino)-anilido- anthracliinon-2-sulfonsäure in<B>1200</B> Teilen Wasser. Man rührt bei 20'<B>3</B> bis 4 Stunden und giesst allmählich 50 Teile 10%ige Na triumkarbonatlösung dazu, so dass die Reak tion immer neutral bleibt. Dann gibt man eine neutrale Lösung von 28,9 Teilen 2- Amino-5-oxynaphthalin-7-sulfonsäure und 14 Teilen kristallisiertem Natriumacetat in 1000 Teilen Wasser dazu. Man erhöht nun die Temperatur auf 40 bis 45 und rührt 24 Stunden.
Dann wird mit Natriumkarbonat lösung genau neutralisiert und 18,6 Teile Anilin zugegeben. Man erhitzt das Ganze während 2 Stunden auf<B>90',</B> macht durch Zugabe von Natriumkarbonat alkalisch und salzt den gebildeten Farbstoff aus.
Process for the production of a new dye of the anthraehinone series. It has been found that a new dye of the anthraquinone series is obtained if 1 mol of 1 amino-4- (4'-amino) -anilidoanthraquinone-2-sulfonic acid is added to 1 mol of cyanuric chloride, 1.
Mol of 2-amino-5-oxynaphthalene-7-sulfonic acid and 1 mol of aniline can act in such a way that each halogen atom of the cyanuric chloride is replaced by 1 mol of each of the three other starting materials.
The new dye forms a dark powder that dissolves in water with a blue color and dyes cotton, viscose rayon, wool or silk in greenish-blue shades of good lightfastness.
Example: 18.5 parts of cyanuric chloride are finely suspended in 800 parts of water. A neutral solution of 40.8 parts of 1-amino-4- (4'-amino) -anilido-anthracliinone-2-sulfonic acid in 1200 parts of water is poured into this suspension. The mixture is stirred at 20-3 to 4 hours and gradually 50 parts of 10% sodium carbonate solution are added so that the reaction always remains neutral. A neutral solution of 28.9 parts of 2-amino-5-oxynaphthalene-7-sulfonic acid and 14 parts of crystallized sodium acetate in 1000 parts of water are then added. The temperature is now increased to 40 to 45 and the mixture is stirred for 24 hours.
Then it is exactly neutralized with sodium carbonate solution and 18.6 parts of aniline are added. The whole is heated to <B> 90 'for 2 hours, </B> making it alkaline by adding sodium carbonate and salting out the dye formed.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH181719T | 1934-11-13 | ||
| CH178548T | 1938-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH181719A true CH181719A (en) | 1935-12-31 |
Family
ID=25720173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH181719D CH181719A (en) | 1934-11-13 | 1934-11-13 | Process for the production of a new dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH181719A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041912B (en) * | 1954-11-29 | 1958-10-30 | Ici Ltd | Process for dyeing or printing cellulosic textile fabrics |
| DE1183187B (en) * | 1960-11-14 | 1964-12-10 | Ciba Geigy | Process for the preparation of dyes of the anthraquinone series |
-
1934
- 1934-11-13 CH CH181719D patent/CH181719A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1041912B (en) * | 1954-11-29 | 1958-10-30 | Ici Ltd | Process for dyeing or printing cellulosic textile fabrics |
| DE1183187B (en) * | 1960-11-14 | 1964-12-10 | Ciba Geigy | Process for the preparation of dyes of the anthraquinone series |
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