CH133386A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH133386A CH133386A CH133386DA CH133386A CH 133386 A CH133386 A CH 133386A CH 133386D A CH133386D A CH 133386DA CH 133386 A CH133386 A CH 133386A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- blue
- production
- diamino
- anthraquinone derivative
- Prior art date
Links
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/515—N-alkyl, N-aralkyl or N-cycloalkyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderivates. Es wurde gefunden, dass man ein Anthra- chinonderivat erhält, wenn man das tech nische Gemisch der 4,5-Diamino-1,8-dioxy- anthrachinon-2,7-disulfosäure und der 4,8- Diamino -1,5 - dioxyanthrachinon - 2,6 - disulfo - säure, Formaldehyd und Ameisensäure auf einander einwirken lässt.
Das so erhaltene Produkt stellt wahrscheinlich ein Gemisch der N-Dirnethylderivate der genannten Säu ren dar und .kann durch die Einwirkung der Ameisensäure auf das Kondensationsprodukt des Aldehydes mit dem Aminoanthrachinon oder durch die Einwirkung des Aldehydes auf das Kondensationsprodukt der Ameisen säure mit dem Aminoanthrachinon entstanden sein, Es bildet ein dunkelblaues, in Wasser mit reinblauer Farbe lösliches Pulver. Die wässerige Lösung bleibt auf Zusatz von Salzsäure blau. Der neue Farbstoff färbt Wolle aus saurem Bad in reinen, blauen Tönen.
<I>Beispiel:</I> 10 Teile des technischen Gemisches der 4,5-Diamino-1,8-dioxyanthrachinori-2,7-disulfo- säure und der 4,8-Dianiino-1,5-dioxyanthra- chinon-2,6-disulfosäure werden im emaillierten Kessel mit 60 Teilen Ameisensäure 83.5 /a und 25 Teilen Formaldehyd von 40 Vol. /o bei Wasser badtemperatur so lange behandelt, bis die anfangs violettblaue Farbe der Schmelze in grünblau übergegangen und keine weitere Nuancenänderung mehr zeigt.
Die Schmelze wird alsdann mit Wasser ver dünnt, mit Kochsalz ausgesalzen, abfiltriert und getrocknet.
Process for the production of an anthraquinone derivative. It has been found that an anthraquinone derivative is obtained if the technical mixture of 4,5-diamino-1,8-dioxy-anthraquinone-2,7-disulfonic acid and 4,8-diamino -1,5 - dioxyanthraquinone - 2,6 - disulfonic acid, formaldehyde and formic acid can act on each other.
The product obtained in this way is probably a mixture of the N-dimethyl derivatives of the acids mentioned and may have been formed by the action of formic acid on the condensation product of the aldehyde with the aminoanthraquinone or by the action of the aldehyde on the condensation product of the formic acid with the aminoanthraquinone , It forms a dark blue powder that is soluble in water with a pure blue color. The aqueous solution remains blue when hydrochloric acid is added. The new dye dyes wool from an acid bath in pure, blue tones.
<I> Example: </I> 10 parts of the technical mixture of 4,5-diamino-1,8-dioxyanthraquinori-2,7-disulfonic acid and 4,8-dianiino-1,5-dioxyanthraquinone 2,6-disulfonic acid are treated in an enamelled kettle with 60 parts of formic acid 83.5 / a and 25 parts of formaldehyde at 40 vol. / O at water bath temperature until the initially violet-blue color of the melt changes to green-blue and shows no further changes in nuance.
The melt is then diluted with water, salted out with sodium chloride, filtered off and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH133386T | 1926-08-26 | ||
| CH131358T | 1927-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH133386A true CH133386A (en) | 1929-05-31 |
Family
ID=25711602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH133386D CH133386A (en) | 1926-08-26 | 1926-08-26 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH133386A (en) |
-
1926
- 1926-08-26 CH CH133386D patent/CH133386A/en unknown
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