CH196655A - Process for the preparation of an anthraquinone dye. - Google Patents
Process for the preparation of an anthraquinone dye.Info
- Publication number
- CH196655A CH196655A CH196655DA CH196655A CH 196655 A CH196655 A CH 196655A CH 196655D A CH196655D A CH 196655DA CH 196655 A CH196655 A CH 196655A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- green
- blue
- color
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000001000 anthraquinone dye Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000975 dye Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 210000002268 wool Anatomy 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000013535 sea water Substances 0.000 claims description 2
- 239000001046 green dye Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000005406 washing Methods 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
- C09B1/325—Dyes with no other substituents than the amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines Antbrachinonfarbstoffes. Es wurde gefunden, dass -wertvolle Farb- stoffe,der Anthra#ellinonreihe entstehen, wenn man Chinizarin respektive lieukoehinizarin oder andere Anthrachinonderivate, welche in 1,4-iS.tellung leicht austauschbare Substit-u- enten, wie z.
B. Ralogen oder Offl, enthal ten, mit Amino,diplienyläthern und ihren Homologen kondensiert und die entstehenden Farbba,sen vonder allgemeinen Formel
EMI0001.0018
sulfoniert, wodurch zwei iSu-Ifonsäuregruppen ins Farbstoffmolekül eintreten.
Die mitden neuen Farbstoffen auf Wolle erzielten Färbungen sind echt gegen kräfti- es Waschen und Walken. Sie weisen, beson ders wenn sie mitSchwefelsäure gef"itrbt wor den sind, eine gute Pottingeolith--it auf. Gleichzeitig zeichnen sie sich durch erhöhte Licht- und Alkaliechtheiten aus, mit welchen Eigensss'haften sie äänliche Farbstoffe des Handels übertreffen.
Gegenstaad des vorliegenden Patentes ist ein Verfahren zur Herstellung eines neuen, sauren Anthrachinonfarbsteffe"s, das darin be,steht,,da.ss,die in üblicher Weise aus einem Anthrachinonderivat, das in den iStellungen <B>1</B> und 4 leicht austauschbare Substituenten besitzt, wie beispielsweise Chinizarin, Leuko- chinizarin, deren Gemisch oder 1,4-Dichlor- antlira,chinon, und 4-Ami-no,
diplienyläther her gestellte r' arbba-se,der Formel
EMI0001.0047
mit sulfonierenden Mitteln in die Farbstoff- di,sulfon,säure übergeführt,,diese isoliert und mit Soda neutralisiert wird.
Getrocknet und gemahlen stellt der neue Farbstoff ein dunkelgrünes Pulver dar, das sieh leicht in Wasser mit blaugrüner Farbe löst und auf Wolle sauer blaugräne Fiirl.)uii- gen er,-JU die sie.li durch gute Potthig-, Lieht-# Alkali- und Seewassereelitbeit aus zeichnen.
<I>Beispiel:</I> reile 4-Amiiiodiplieiiylä er, 40 Teile Chinizarin, <B>30</B> Teile Lei-tl-,oeb.in-izai-ilii und <B>30</B> Teile BorsäLire werden unter Rübrenso lange auf<B>110 ' C</B> erhitzt, bis die M7as#jerd#iiiipf(,iit- wiel:lung aufgehört hat und sieb die anfäll11,- lieh blaue Farbe der Schmelze nicht melir weiter nach Grän verschiebt.
Nach dem Erhalteii wird die spröde MaAse gepulvert, durch Aufkochen mit verdümiter Salzsäure der unverändert(. Aminodiphenyl- äther lieri-iLis"-;,elöst und zurüAgewonnen.
Die Farbbase kann durch Behandeln mit heissem Sprit, weiter gereinigt werden.
Sie wird als dunkelblaues Pulver erlial- ten. das sieb. in Chlorbetizol mit lebhafter blau-,rüner und in konz. Sehwefelsäure mit n blauer Farbe löst.
Z,%7#,-e#cks Sulfonierung werden 4 Teile Farbbase in -)() Teile konz. Schwefelsäure bei <B>30 ' C</B> ein- tragen.<B>'</B> _-e <B>,</B> Nach Rüh ren giesst man auf Eis. Die abgeschiedone Disulfonsäure wird in warmeiii Wasser init So#da, alkalisch gelöst und der Farbstoff durch weiiig Salz gefällt.
Getroaknet und -emahlen stellt er ein daii1z4-,1",rüi)#"s Pulver dar, das sieh leicht in e# Wasser mit blaugrünür Farbe löst. Auf Wolle lassen sieli sauer blaLiggrüne, potting- eellte, Färbungeii ei-7iel(,ii, die isich durch ihre <B>M</B> Liebt-. Alkali- und Seewassei-eebtlieit aus zeichnen.
Process for the preparation of an antbrachinone dye. It has been found that valuable dyes of the anthraquinone series are formed when quinizarine or lieukoehinizarin or other anthraquinone derivatives, which in the 1,4-position are easily interchangeable, such as eg.
B. Ralogen or Offl, condensed with amino, diplomatic ethers and their homologues and the resulting color bases from the general formula
EMI0001.0018
sulfonated, whereby two iSu-Ifonic acid groups enter the dye molecule.
The dyeings achieved on wool with the new dyes are resistant to vigorous washing and fulling. They have a good pottingeolite, especially when they have been colored with sulfuric acid. At the same time, they are characterized by increased light and alkali fastness properties, with which they surpass similar commercial dyes.
The subject of the present patent is a process for the production of a new, acidic anthraquinone dye that is contained therein, that is, that is produced in the usual manner from an anthraquinone derivative that is found in positions <B> 1 </B> and 4 has easily interchangeable substituents, such as quinizarin, leucoquinizarin, their mixture or 1,4-dichloro-antlira, quinone, and 4-amino,
diplienylether made r 'arbba-se, the formula
EMI0001.0047
with sulfonating agents converted into the dye di, sulfonic acid, this is isolated and neutralized with soda.
Dried and ground, the new dye is a dark green powder that easily dissolves in water with a blue-green color and turns acidic blue-green filaments on wool.) You can find it, -JU, which you.li by good potthig-, Lieht- and maritime elite work.
<I> Example: </I> reile 4-Amiiiodiplieiiylä er, 40 parts quinizarin, <B> 30 </B> parts Lei-tl-, oeb.in-izai-ilii and <B> 30 </B> parts Borsals are heated under Rübrens to <B> 110 'C </B> until the M7as # jerd # iiiipf (, iit- wiel: lung has stopped and sieve the accrued blue color of the melt no further to Grän shifts.
After receiving it, the brittle substance is powdered, dissolved and recovered by boiling with dilute hydrochloric acid of the unchanged (. Aminodiphenyl ether lieri-iLis "-;).
The color base can be cleaned further by treating it with hot fuel.
It is obtained as a dark blue powder. The sieve. in chlorobetizole with lively blue, green and conc. Sulfuric acid dissolves with a blue color.
Z,% 7 #, - e # cks sulfonation, 4 parts of color base are in -) () parts of conc. Enter sulfuric acid at <B> 30 'C </B>. <B>' </B> _-e <B>, </B> After stirring, pour onto ice. The separated disulfonic acid is dissolved in warm water with soot, alkaline, and the dye is precipitated with white salt.
When drunk and ground, it represents a daii1z4-, 1 ", rüi) #" s powder, which easily dissolves in e # water with a blue-green color. On wool, you can have sour pale green, potted, potted, dyed colors (, ii, which are characterized by their <B> M </B> love, alkali and sea water quality.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH196655T | 1937-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH196655A true CH196655A (en) | 1938-03-31 |
Family
ID=4440483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH196655D CH196655A (en) | 1937-03-11 | 1937-03-11 | Process for the preparation of an anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH196655A (en) |
-
1937
- 1937-03-11 CH CH196655D patent/CH196655A/en unknown
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