CH203043A - 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
- CH203043A CH203043A CH203043DA CH203043A CH 203043 A CH203043 A CH 203043A CH 203043D A CH203043D A CH 203043DA CH 203043 A CH203043 A CH 203043A
- Authority
- CH
- Switzerland
- Prior art keywords
- new dye
- mol
- anthraquinone series
- production
- benzidine
- 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
- 239000007859 condensation product Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- 241000974482 Aricia saepiolus Species 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 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
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 230000001180 sulfating effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 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 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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
Zusatzpatent zum Hauptpatent Nr. 178548. Verfahren zur Herstellung eines neuen Farbstoffes der Anthrachinonreihe. Fis wurde gefunden, dass man einen neuen Farbstoff der Anthraehinonreihe erhält,
wenn man auf i Hol Phosgen 2 Mol des Kondensationsproduktes aus 1 Mol 1-Amino- 4-bromanthraobinon-2-sulfonsäure und der jenigen Ben.zidinmonosulfonsäure, die erhal ten wird durch Sulfieren von Benzidin,der- art einwirken lässt,
@dass je ein Halogenatom des Phosgens mit je einem Wasserstoffatom der NHZ-Gruppe des Benzidinsulfon6äure- restes reagiert.
Der neue Farbstoff bildet ein dunkles Pulver, das sich in Wasser mit blauer Farbe löst und Viskosekunstseide oder Baumwolle in reinen grünstichig-blauen Tönen von sehr guter Lichteohtheit färbt.
<I>Beispiel</I> 57 Teile .des Kondensationsproduktes aus 1-Amino-4-bromanthrachänon- 2 -sulfonsäure und Benzidinsulfonsäure werden in 3000 Tei- len Wasser durch Zugabe von 30 Teilen Na- triumcarbonat gelöst. In diese Lösung wird Phossgen eingeleitet,
bis sich kein mehr' nachweisen lässt. Gleichzeitig werden weitere 30 Teile Natriumearbonat in kleinen Portionen zugegeben, so dass die Reaktion der Lösung stets 'schwach alkalisch bleibt. Der ausgefallene Farbstoff wird ab filtriert und getrocknet.
Additional patent to main patent no. 178548. Process for the production of a new dye from the anthraquinone series. Fis it was found that a new dye of the anthraehinone series is obtained,
if 2 moles of the condensation product of 1 mole of 1-amino-4-bromanthraobinone-2-sulfonic acid and the benzidine monosulfonic acid obtained by sulfating benzidine are allowed to act in this way,
@that one halogen atom of phosgene reacts with one hydrogen atom of the NHZ group of the benzidinesulfonic acid residue.
The new dye forms a dark powder that dissolves in water with a blue color and dyes viscose rayon or cotton in pure greenish-blue shades of very good lightness.
<I> Example </I> 57 parts of the condensation product of 1-amino-4-bromoanthraquinone-2-sulfonic acid and benzidine sulfonic acid are dissolved in 3000 parts of water by adding 30 parts of sodium carbonate. Phossgene is introduced into this solution,
until no more 'can be detected. At the same time, a further 30 parts of sodium carbonate are added in small portions, so that the reaction of the solution always remains slightly alkaline. The precipitated dye is filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH178548T | 1938-02-19 | ||
| CH203043T | 1938-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203043A true CH203043A (en) | 1939-02-15 |
Family
ID=25720177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203043D CH203043A (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) | CH203043A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2475530A (en) * | 1946-03-18 | 1949-07-05 | Ici Ltd | Process for making aminoanthraquinone sulfonic acids |
-
1938
- 1938-02-19 CH CH203043D patent/CH203043A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2475530A (en) * | 1946-03-18 | 1949-07-05 | Ici Ltd | Process for making aminoanthraquinone sulfonic acids |
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