CH203430A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH203430A CH203430A CH203430DA CH203430A CH 203430 A CH203430 A CH 203430A CH 203430D A CH203430D A CH 203430DA CH 203430 A CH203430 A CH 203430A
- Authority
- CH
- Switzerland
- Prior art keywords
- anthraquinone
- mixture
- amino
- leuco compounds
- dye
- 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 9
- 150000004056 anthraquinones Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 3
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 229920003086 cellulose ether Polymers 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- AQXYVFBSOOBBQV-UHFFFAOYSA-N 1-amino-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2N AQXYVFBSOOBBQV-UHFFFAOYSA-N 0.000 description 1
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000080 wetting agent 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
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/285—Dyes with no other substituents than the amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes der Anthrachinonreihe. Es wurde gefunden, dass man einen wert vollen, neuen Farbstoff der Anthrachinon- reihe erhält, wenn man Anthrachinonabkömm- linge vom allgemeinen Aufbau
EMI0001.0007
worin X und Y austauschfähige Reste be deuten, die die Überführung der Anthrachi- nonabkömmlinge in ihre Leukoverbindungen gestatten, wie z. B.
OH, 0-Alkyl oder NH2, teilweise in Form ihrer Leukoverbindungen mit einem Gemisch von Amino-2,3-propan- diol und Aminoäthanol umsetzt. Der so er haltene Endstoff wird, da er zum Teil in Form seiner Leukoverbindung vorliegt, nach träglich oxydiert.
Ausgangsstoffe sind zum Beispiel 1,4-Di- oxyanthrachinon, 1,4-Diaminoanthrachinon, 1-Amino-4-oxyanthrachinon, 1-Amino-4-me- thoxyanthrachinon, 1-Ogy-4-methoxyanthra- chinon und 1,4-Dimethogyanthrachinon.
In vielen Fällen ist es nicht erforderlich, von den fertigen Leukoverbindungen auszu gehen, sondern man kann auch die Anthra- cIiinonabkömmlinge in Gegenwart eines Re duktionsmittels, wie Zinkstaub oder Na- triumhydrosulfit, verwenden.
Der so erhaltene Endstoff liefert auf Celluloseestern und -äthern Färbungen von hoher Klarheit und guter Echtheit. Ein be sonderer Vorzug liegt in seiner guten Was serlöslichkeit, so dass man beim Färben aus wässerigem Bad vielfach ohne Zusatz von verteilend oder netzend wirkenden oder an dern Färbereihilfsmitteln auskommt.
<I>Beispiel:</I> Eine Mischung von 24 Teilen 1,4-Dioxy- anthrachinon, 6 Teilen Leuko-1,4-dioxy- anthrachinon und 160 Teilen Isobutanol wird bei 60 C unter Rühren mit einer Mischung von 13,6 Teilen 1-Amino-2,3-propandiol und 9,2 Teilen Aminoäthanol versetzt.
Das Ge misch rührt man zunächst 2 Stunden lang bei 60 C, erhitzt es dann zum Sieden und kocht es so lange unter Rühren und Rückflussküh- lung, bis in einer Probe kein 1,4-Dioxy- anthra.chinon mehr nachweisbar ist. Zur Oxydation geringer Mengen Leukoverbin- dung leitet man Luft durch das Gemisch und befreit es mittels Wasserdampf vom Isobutanol, wobei die Hauptmenge der ent standenen Verbindung mit blauer Farbe in Lösung geht.
Nach Zugabe von Tierkohle filtriert man von geringen Mengen ungelöster Anteile ab und salzt den entstandenen Stoff aus der tiefblauen Mutterlauge nach Zugabe von etwas Natronlauge mit Kochsalz aus. Er be steht aus einem Gemisch von hauptsächlich 1-Propandiol - amino -4 - äthanola.minoanthra chinon und wenig 1,4-Dipropa.ndi.olamino- anthraehinon, während das gleichfalls in ge ringer -Menge entstandene wasserunlösliche 1,4-Di-(äthanolamino)-anthra.chinon durch Filtrieren der wässrigen Lösung als wasser unlöslicher Anteil abgetrennt wird.
Der so erhaltene blaue Farbstoff löst sich in Schwefelsäure mit blaustichig roter Farbe. In warmem Wasser löst er sich mit tief blauer Farbe und liefert auf Celluloseäthern und -estern kräftige blaue Färbungen von hervorragender Echtheit.
Process for the preparation of a dye of the anthraquinone series. It has been found that a valuable, new dye of the anthraquinone series is obtained if anthraquinone derivatives of the general structure are used
EMI0001.0007
where X and Y are interchangeable residues that allow the conversion of the anthraquinone derivatives into their leuco compounds, such as. B.
OH, O-alkyl or NH2, partly in the form of their leuco compounds, with a mixture of amino-2,3-propanediol and aminoethanol. The end product thus obtained is, since it is partly in the form of its leuco compound, subsequently oxidized.
Starting materials are, for example, 1,4-dioxyanthraquinone, 1,4-diaminoanthraquinone, 1-amino-4-oxyanthraquinone, 1-amino-4-methoxyanthraquinone, 1-Ogy-4-methoxyanthraquinone and 1,4- Dimethogyanthraquinone.
In many cases it is not necessary to start from the finished leuco compounds, but the anthraciinone derivatives can also be used in the presence of a reducing agent such as zinc dust or sodium hydrosulfite.
The end product thus obtained provides colorations of high clarity and good fastness on cellulose esters and ethers. A particular advantage is its good solubility in water, so that dyeing from an aqueous bath often does not require the addition of dispersing or wetting agents or other dyeing auxiliaries.
<I> Example: </I> A mixture of 24 parts of 1,4-dioxy-anthraquinone, 6 parts of leuco-1,4-dioxy-anthraquinone and 160 parts of isobutanol is mixed with a mixture of 13.6 at 60 ° C. while stirring Parts of 1-amino-2,3-propanediol and 9.2 parts of aminoethanol are added.
The mixture is first stirred for 2 hours at 60 C, then heated to the boil and boiled while stirring and refluxing until no more 1,4-dioxyanthraquinone can be detected in a sample. In order to oxidize small amounts of leuco compounds, air is passed through the mixture and isobutanol is removed from it by means of steam, with the majority of the resulting compound dissolving with a blue color.
After adding animal charcoal, small amounts of undissolved fractions are filtered off and the resulting substance is salted out from the deep blue mother liquor after adding a little sodium hydroxide solution with common salt. It consists of a mixture of mainly 1-propanediol - amino -4 - äthanola.minoanthraquinone and a little 1,4-Dipropa.ndi.olaminoanthraehinone, while the water-insoluble 1,4-di- (Ethanolamino) anthraquinone is separated off as a water-insoluble fraction by filtering the aqueous solution.
The blue dye thus obtained dissolves in sulfuric acid with a bluish red color. In warm water it dissolves with a deep blue color and, on cellulose ethers and esters, provides strong blue colorations of excellent fastness.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE203430X | 1936-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203430A true CH203430A (en) | 1939-03-15 |
Family
ID=5776390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203430D CH203430A (en) | 1936-12-23 | 1937-11-27 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203430A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2060048A2 (en) * | 1969-07-18 | 1971-06-11 | Sandoz Sa |
-
1937
- 1937-11-27 CH CH203430D patent/CH203430A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2060048A2 (en) * | 1969-07-18 | 1971-06-11 | Sandoz Sa |
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