CH130621A - Process for the production of a new anthraquinone derivative. - Google Patents
Process for the production of a new anthraquinone derivative.Info
- Publication number
- CH130621A CH130621A CH130621DA CH130621A CH 130621 A CH130621 A CH 130621A CH 130621D A CH130621D A CH 130621DA CH 130621 A CH130621 A CH 130621A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- anthraquinone derivative
- new dye
- new anthraquinone
- new
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 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 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture 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
- C09B1/32—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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Anthrachinonderivates. Es wurde gefunden, dass man einen neuen Farbstoff der Anthrachinonreihe erhält, wenn man auf eine Verbindung der allgemeinen Formel
EMI0001.0004
in welcher x für einen gegen Aminoarylreste austauschfähigen Rest, wie NHz, OH, OCHS, steht, m-Phenylendiamin einwirken lässt. Der neue Farbstoff schmilzt bei 197-198 (aus Anilin umkristallisiert), löst sich in organi schen Lösungsmitteln mit rein blauer und in konzentrierter Schwefelsäure mit violetter Farbe.
Er erzeugt auf Acetatseide reine blaue Färbungen.
<I>Beispiel:</I> 25,4 Teile 1-Methoxy-4-aminoanthrachinon werden mit 40 Teilen m-Phenylendiamin und 100 Teilen Dimethylanilin so lange auf 1S0 erhitzt, bis eine Probe in Alkohol keine Ver schiebung der Nuance mehr aufweist. Man versetzt bei 100 mit 140 Teilen Methylal kohol und nutscht nach dem Erkalten ab. Das 1-(3'-Amino)-phenyl-4-amino-anthrachinon scheidet sich in guter Ausbeute ab. Es wird filtriert und getrocknet.
Process for the production of a new anthraquinone derivative. It has been found that a new dye of the anthraquinone series is obtained when a compound of the general formula
EMI0001.0004
in which x stands for a radical that can be exchanged for aminoaryl radicals, such as NHz, OH, OCHS, allows m-phenylenediamine to act. The new dye melts at 197-198 (recrystallized from aniline), dissolves in organic solvents with a purely blue color and in concentrated sulfuric acid with a purple color.
He creates pure blue colors on acetate silk.
<I> Example: </I> 25.4 parts of 1-methoxy-4-aminoanthraquinone are heated to 50 with 40 parts of m-phenylenediamine and 100 parts of dimethylaniline until a sample in alcohol no longer shows any shift in shade. 140 parts of methyl alcohol are added at 100 and the mixture is filtered off with suction after cooling. The 1- (3'-amino) -phenyl-4-amino-anthraquinone separates out in good yield. It is filtered and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH127530T | 1927-02-12 | ||
| CH130621T | 1927-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH130621A true CH130621A (en) | 1928-12-15 |
Family
ID=25710925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH130621D CH130621A (en) | 1927-02-12 | 1927-02-12 | Process for the production of a new anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH130621A (en) |
-
1927
- 1927-02-12 CH CH130621D patent/CH130621A/en unknown
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