CH209263A - 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
- CH209263A CH209263A CH209263DA CH209263A CH 209263 A CH209263 A CH 209263A CH 209263D A CH209263D A CH 209263DA CH 209263 A CH209263 A CH 209263A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzidine
- new dye
- mol
- amino
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 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
- ZBZGGZGVFCIXDE-UHFFFAOYSA-N 5-amino-2-(4-aminophenyl)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O ZBZGGZGVFCIXDE-UHFFFAOYSA-N 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- QZZSAWGVHXXMID-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(O)(=O)=O)C(N)=C3C(=O)C2=C1 QZZSAWGVHXXMID-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 229920000297 Rayon Polymers 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 150000008061 acetanilides Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
<B>Zusatzpatent</B> zum Hauptpatent Nr. 178548. Verfahren zur Herstellung eines neuen Farbstoffes der Anthrachinonreihe. Es wurde gefunden, dass man einen neuen Farbstoff der Anthrachinonreihe erhält, wenn man auf 1 Mol Cyanurchlorid 2 Mol des Kondensationsproduktes aus 1-Amino-4- bromanthrachinon-2-sulfonsäure und derjeni gen Benzidinmonosulfonsäure, die erhalten wird durch Sulfieren des Benzidins,
und 1 Mol p-Aminoacetanilid derart einwirken lässt, dass zwei Halogenatome des Cyanur- ehlorids mit je einem Wasserstoffatom der Aminogruppe des Benzidinsulfonsäurerestes des Kondensationsproduktes und ein Ha logenatom mit einem Wasserstoffatom der Aminogruppe des p-Aminoacetanilids rea gieren.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blauer Farbe löst und Viskosekun@stseid-e oder Baumwolle in reinen grünstichig-blauen Tönen von sehr guter Dichtechtheit färbt. <I>Beispiel:</I> Zu einer feinen Suspension von 18,5 Tei len Cyanurchlorid in 800 Teilen Wasser wer- den bei 5 118 Teile des Kondensations produktes aus 1-Amino-4-bromanthrachinon- 2-sulfonsäure und Benzidinsulfonsäure in 2000 Teilen Wasser zugegeben. Man rührt 4 bis 5 Stunden bei 10 bis 15 und erhöht dann die Temperatur allmählich auf 85 bis 40'.
Durch Zutropfen einer 10%igen Na- triumcarbonatlösung hält man die Reaktion stets neutral. Wenn die Kondensation be endet ist, gibt man 20 Teile p-Aminoacet- anilid dazu und erhitzt unter gutem Rühren noch 1 @Stunde auf 9,0 bis <B>95'.</B> Dann stellt man die Reaktionsmasse mit Natriumcarbo- nat alkalisch und salzt den gebildeten Farb stoff aus.
<B> Additional patent </B> to main patent no. 178548. Process for the production of a new dye from the anthraquinone series. It has been found that a new dye of the anthraquinone series is obtained if, for 1 mole of cyanuric chloride, 2 moles of the condensation product of 1-amino-4-bromoanthraquinone-2-sulfonic acid and the benzidine monosulfonic acid obtained by sulfating the benzidine,
and 1 mole of p-aminoacetanilide is allowed to act in such a way that two halogen atoms of the cyanuric chloride react with one hydrogen atom of the amino group of the benzidine sulfonic acid residue of the condensation product and one halogen atom with one hydrogen atom of the amino group of the p-aminoacetanilide.
The new dye forms a dark powder which dissolves in water with a blue color and dyes viscose silk or cotton in pure greenish-blue shades with very good impermeability. <I> Example: </I> A fine suspension of 18.5 parts of cyanuric chloride in 800 parts of water is converted into 118 parts of the condensation product of 1-amino-4-bromoanthraquinone-2-sulfonic acid and benzidine sulfonic acid in 2000 Parts of water are added. The mixture is stirred for 4 to 5 hours at 10 to 15 and then the temperature is gradually increased to 85 to 40 '.
The reaction is always kept neutral by adding a 10% strength sodium carbonate solution. When the condensation is over, 20 parts of p-aminoacetanilide are added and the mixture is heated to 9.0 to 95 'for 1 hour with thorough stirring. The reaction mixture is then made up with sodium carbonate alkaline and salt out the dye formed.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH209263T | 1938-02-19 | ||
| CH178548T | 1938-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209263A true CH209263A (en) | 1940-03-31 |
Family
ID=25720179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209263D CH209263A (en) | 1938-02-19 | 1938-02-19 | Process for the production of a new dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209263A (en) |
-
1938
- 1938-02-19 CH CH209263D patent/CH209263A/en unknown
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