CH212801A - Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. - Google Patents
Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative.Info
- Publication number
- CH212801A CH212801A CH212801DA CH212801A CH 212801 A CH212801 A CH 212801A CH 212801D A CH212801D A CH 212801DA CH 212801 A CH212801 A CH 212801A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- derivative
- tetrahydroanthraquinone
- preparation
- leuco
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 210000002268 wool Anatomy 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000006277 sulfonation reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000003756 stirring 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
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
-
- 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
-
- 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
-
- 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
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen 6.6._7.8-Tetrahydro- anthrachinonderivates. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellung eines stickstoff haltigen 5.6.7.8-Tetrahydroanthrachinon- derivates, welches darin besteht, dass man Leuko-5 . 6 . 7 . 8-tetrahydrochinizarin mit 4- Cyclohexylanilin umsetzt und die Leukover- bindung oxydiert.
Die so erhaltene neue Verbindung bildet blaue Prismen vom Schmelzpunkt 219 bis 221 C. Die Lösungsfarbe in konzentrierter Schwefelsäure ist violett. Die daraus durch Sulfonieren gebildete Sulfonsäure färbt Wolle in grünen Tönen.
<I>. Beispiel:</I> 12 Gewichtsteile Leuko-5.6.7.8-tetra- hydrochinizarin werden mit 100 Gewichts teilen 4-Cyclohexylanilin und 8 Gewichts teilen Borsäure unter Rühren 3 Stunden auf 100 bis 110 C erhitzt; dann leitet man 1 Stunde Luft über oder in die Schmelze und verdünnt nach dem Abkühlen auf 80 C mit etwa 150 bis 200 Gewichtsteilen Metha nol. Beim Erkalten scheidet sich in sehr guter Ausbeute ein Kondensationsprodukt ab, das- aus Chlorbenzol in blauen Prismen vom Schmelzpunkt 219 bis 221 C kristalli siert. Die -Lösungsfarbe in konzentrierter Schwefelsäure ist violett.
Der in üblicher Weise sulfonierte Farbstoff. färbt Wolle in grünen Tönen von guten Echtheitseigen schaften.
Process for the production of a nitrogen-containing 6.6._7.8-tetrahydro-anthraquinone derivative. The subject of this additional patent is a process for the production of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative, which consists of leuco-5. 6th 7th 8-tetrahydroquinizarin reacts with 4-cyclohexylaniline and oxidizes the leuco compound.
The new compound thus obtained forms blue prisms with a melting point of 219 to 221 C. The solution color in concentrated sulfuric acid is violet. The sulfonic acid formed from it by sulfonation dyes wool in green shades.
<I>. Example: 12 parts by weight of leuco-5.6.7.8-tetrahydroquinizarin are heated with 100 parts by weight of 4-cyclohexylaniline and 8 parts by weight of boric acid for 3 hours at 100 to 110 ° C with stirring; then air is passed over or into the melt for 1 hour and, after cooling to 80 ° C., diluted with about 150 to 200 parts by weight of methanol. On cooling, a condensation product separates out in very good yield, which crystallizes from chlorobenzene in blue prisms with a melting point of 219 to 221 C. The solution color in concentrated sulfuric acid is purple.
The conventionally sulfonated dye. dyes wool in green shades with good fastness properties.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE212801X | 1937-12-24 | ||
| DE150138X | 1938-01-15 | ||
| CH210607T | 1938-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212801A true CH212801A (en) | 1940-12-15 |
Family
ID=27177898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212801D CH212801A (en) | 1937-12-24 | 1938-12-17 | Process for the preparation of a nitrogen-containing 5.6.7.8-tetrahydroanthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH212801A (en) |
-
1938
- 1938-12-17 CH CH212801D patent/CH212801A/en unknown
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