CH235571A - Process for the production of a new blue dye of the anthraquinone series. - Google Patents
Process for the production of a new blue dye of the anthraquinone series.Info
- Publication number
- CH235571A CH235571A CH235571DA CH235571A CH 235571 A CH235571 A CH 235571A CH 235571D A CH235571D A CH 235571DA CH 235571 A CH235571 A CH 235571A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- blue dye
- anthraquinone series
- new blue
- acid ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 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 description 3
- 150000004056 anthraquinones Chemical class 0.000 title description 3
- 239000001045 blue dye Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- -1 disulfuric acid ester Chemical class 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quiniazarine Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 102220254284 rs755928199 Human genes 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 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
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen blauen Farbstoffes der Anthrachinonreihe. Im schweizerischen Patent Nr. 232608 ist ein Verfahren zur' Herstellung von blauen Farbstoffen der Anthrachinonreihe beschrie ben, welches darin besteht, dass man in 6- bezw. 7-Stellung halogenierte Chinizarine mit Aminoalkoholen der allgemeinen Formel R-CH-(NH,)-R10H, worin R Alkyl und R, Alkylen bedeuten,
kondensiert und durch Behandlung mit,Sul- fierungsmitteln in die entsprechenden Schwe- felsäureester überführt.
Es wurde nun gefunden, dass man zu glei chen Farbstoffen gelangt, wenn man Schwe- felsäureester der Aminoalkohole der obenge nannten Formel als Ausgangsprodukte be nutzt.
Das vorliegende Patent betrifft ein Ver fahren zur Herstellung des Dischwefelsäure- esters des 1.4-Di-(butanol-1'-amino-2'-)-6- chloranthrachinons, welches dadurch gekenn zeichnet ist, dass man 1 Mol Leuko-6-chlor- chinizarin mit 2 Mol des Schwefelsäureesters des 2-Aminobutanol-1 kondensiert und die Leukoverbindung oxydiert.
Der so erhaltene Farbstoff löst sich in Wasser mit blauer Farbe und färbt Wolle und andere Textilien in lebhaften blauen Tö nen an.
<I>Beispiel:</I> 12 Teile Leuko-6-chlorchinizarin, 18 Teile des Natriumsalzes des 2-Aminobutanol-l- schwefelsäureesters, 80 Teile Alkohol und 12 Teile Wasser werden bei 50-80 gerührt, bis die Kondensation beendet ist. Nach Oxy dation mit Luft, eventuell bei Gegenwart von Piperidin, Pyridin oder Dimethylanilin und etwas Kupferacetat, wird der Farbstoff durch Filtration und Waschen mit Alkohol isoliert und gegebenenfalls durch Kristallisation ge reinigt. Er färbt Wolle und andere Textilien in lebhaften blauen Tönen an.
Process for the production of a new blue dye of the anthraquinone series. In Swiss patent no. 232608 a process for the 'production of blue dyes of the anthraquinone series is described ben, which consists in that one in 6- respectively. 7-position halogenated quinizarines with amino alcohols of the general formula R-CH- (NH,) - R10H, where R is alkyl and R, is alkylene,
condensed and converted into the corresponding sulfuric acid esters by treatment with sulphurizing agents.
It has now been found that the same dyes are obtained if sulfuric acid esters of the amino alcohols of the above formula are used as starting materials.
The present patent relates to a process for the preparation of the disulfuric acid ester of 1,4-di- (butanol-1'-amino-2 '-) - 6-chloroanthraquinone, which is characterized in that 1 mole of leuco-6-chlorine is used - Quinizarin condensed with 2 moles of the sulfuric acid ester of 2-aminobutanol-1 and oxidized the leuco compound.
The dye thus obtained dissolves in water with a blue color and stains wool and other textiles in vivid blue tones.
<I> Example: </I> 12 parts of leuco-6-chloroquinizarin, 18 parts of the sodium salt of 2-aminobutanol-1-sulfuric acid ester, 80 parts of alcohol and 12 parts of water are stirred at 50-80 until the condensation has ended. After oxidation with air, possibly in the presence of piperidine, pyridine or dimethylaniline and a little copper acetate, the dye is isolated by filtration and washing with alcohol and optionally purified by crystallization. He dyes wool and other textiles in vivid blue tones.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH235571T | 1942-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH235571A true CH235571A (en) | 1944-12-15 |
Family
ID=4459014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH235571D CH235571A (en) | 1942-12-24 | 1942-12-24 | Process for the production of a new blue dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH235571A (en) |
-
1942
- 1942-12-24 CH CH235571D patent/CH235571A/en unknown
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