DE90722C - - Google Patents
Info
- Publication number
- DE90722C DE90722C DENDAT90722D DE90722DA DE90722C DE 90722 C DE90722 C DE 90722C DE NDAT90722 D DENDAT90722 D DE NDAT90722D DE 90722D A DE90722D A DE 90722DA DE 90722 C DE90722 C DE 90722C
- Authority
- DE
- Germany
- Prior art keywords
- alizarin
- solution
- bordeaux
- zinc dust
- pct
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- VBHKTXLEJZIDJF-UHFFFAOYSA-N Quinalizarin Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1O VBHKTXLEJZIDJF-UHFFFAOYSA-N 0.000 claims description 4
- 239000003929 acidic solution Substances 0.000 claims description 2
- 239000003638 reducing agent Substances 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- TZIQWQARHPGHIG-UHFFFAOYSA-N anthrarobin Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C(O)=C21 TZIQWQARHPGHIG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/34—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having three rings
-
- 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
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/08—Dyes containing only OH-groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom 12. März 1896 ab.Patented in the German Empire on March 12, 1896.
Wie in der Patentschrift Nr. 91152 gezeigt ist, sind gewisse Leukooxyanthrachinone dadurch technisch werthvoll, dafs sie sich mit primären aromatischen Aminen zu Leukoverbindungen von grünen Farbstoffen condensiren lassen.As shown in Patent No. 91152, certain leucooxyanthraquinones are thereby technically valuable that they combine with primary aromatic amines to form leuco compounds let condense of green coloring matter.
Ein solches bisher noch nicht beschriebenes Leukooxyanthrachinon läfst sich aus dem Alizarinbordeaux durch Reduction in saurer oder alkalischer Lösung darstellen.Such a hitherto not yet described leucooxyanthraquinone can be derived from the Represent Alizarin Bordeaux by reduction in acidic or alkaline solution.
Beispiel: In eine Lösung von 200 kg 2oproc. Alizarinbordeauxpaste, 1800 kg Wasser, 200 kg Ammoniak und 65 kg Natronlauge von 340 B. werden unter kräftigem Umrühren portionenweise 50 kg Zinkstaub eingetragen, indem man gleichzeitig das Ganze auf 70 bis 80° erwärmt. Example: In a solution of 200 kg 2oproc. Alizarinbordeauxpaste, 1800 kg of water, 200 kg ammonia and 65 kg of sodium hydroxide of 34 0 B. are introduced in portions, 50 kg of zinc dust with vigorous stirring, by heating it at the same time the whole at 70 to 80 °.
Sobald die Lösung eine rein gelbe Farbe angenommen hat, welche sich an der Luft nicht mehr sehr rasch verändert, filtrirt manAs soon as the solution has taken on a pure yellow color, which is reflected in the air no longer changed very quickly, one filters
OHOH
OHOH
OHOH
in 400 kg mit Wasser verdünnter Salzsäure von 33 pCt., wobei sich das Leukoalizarinbordeaux in gelben Flocken abscheidet, welche abfiltrirt, gewaschen und getrocknet werden.in 400 kg hydrochloric acid of 33 pCt. diluted with water, whereby the leucoalizarinbordeaux separates in yellow flakes, which are filtered off, washed and dried.
Durch Umkrystallisiren aus Eisessig, zweckmäfsig unter Zusatz von etwas Zinkstaub und WTasser, erhält man die Leukoverbindung rein in Form von bräunlich gelben Kryställchen. Dieselben sind in organischen Lösungsmitteln ziemlich leicht löslich. In Natronlauge löst sich Leukoalizarinbordeaux mit braungelber Farbe, welche an der Luft infolge von Oxydation unter Bildung von Alizarinbordeaux in Violett übergeht. Die Lösung in cone. Schwefelsäure ist gelb. Beim Erhitzen derselben findet ebenfalls Oxydation zu Alizarinbordeaux statt.By recrystallization from glacial acetic acid, zweckmäfsig the addition of some zinc dust and W ater T, we obtain the leuco compound purely in the form of brownish yellow Kryställchen. They are quite easily soluble in organic solvents. Leucoalizarin bordeaux with a brownish yellow color dissolves in sodium hydroxide solution, which changes to violet in the air as a result of oxidation with the formation of alizarin bordeaux. The solution in cone. Sulfuric acid is yellow. When these are heated, oxidation to alizarin bordeaux also takes place.
Der Elementaranalyse zufolge gehört diese Leukoverbindung der Oxyanthranolstufe an und hat mithin die Constitution:According to the elemental analysis, this leuco compound belongs to the oxyanthranol stage and therefore has the constitution:
OHOH OHOH
COCO
oderor
OHOH
OHOH
Gefunden: Ber. für C14-H10O6:Found: Ber. for C 14 -H 10 O 6 :
C 61,0 pCt. 61,31 pCt.C 61.0 pCt. 61.31 pCt.
H 3,35 - ■ 3>65 - H 3.35 - ■ 3> 6 5 -
Statt mit Zinkstaub kann die Reduction auch mit den anderen üblichen alkalischen Reductionsmitteln, wie z. B. durch Kochen mit Zinn-Instead of using zinc dust, the reduction can also be carried out with the other common alkaline reducing agents, such as B. by cooking with tin
OHOH
oxydulnatron u. s. w., ausgeführt werden. Auch durch Reduction in saurer Lösung, z.B. in Eisessig mit Zinkstaub, kann die oben beschriebene Leukoverbindung erhalten werden.Oxydulnatron and so on. Also through reduction in acidic solution, e.g. in Glacial acetic acid with zinc dust, the leuco compound described above can be obtained.
Nach den gleichen Methoden kann auch das in der Patentschrift. Nr. 89027 beschriebene,The same methods can also be used in the patent specification. No. 89027,
durch Reduction von Alizarinhexacyanin oder Hexaoxyanthrachinon erhaltene Leukopentacyanin aus Alizarinpentacyanin selbst dargestellt werden. Dasselbe ist ebenfalls ein werthvolles Material zur Darstellung von stickstoffhaltigen Farbstoffen.leukopentacyanine obtained by reducing alizarin hexacyanine or hexaoxyanthraquinone from alizarin pentacyanine itself. It is also a valuable one Material for the representation of nitrogenous dyes.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE90722C true DE90722C (en) |
Family
ID=362405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT90722D Active DE90722C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE90722C (en) |
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0
- DE DENDAT90722D patent/DE90722C/de active Active
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