DE71306C - Process for the preparation of stain-coloring dyes from anthradichinones and phenols - Google Patents
Process for the preparation of stain-coloring dyes from anthradichinones and phenolsInfo
- Publication number
- DE71306C DE71306C DENDAT71306D DE71306DA DE71306C DE 71306 C DE71306 C DE 71306C DE NDAT71306 D DENDAT71306 D DE NDAT71306D DE 71306D A DE71306D A DE 71306DA DE 71306 C DE71306 C DE 71306C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- anthradichinones
- phenols
- preparation
- stain
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title description 8
- 239000000975 dye Substances 0.000 title description 7
- 150000002989 phenols Chemical class 0.000 title description 4
- 238000004040 coloring Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 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 12
- 150000004053 quinones Chemical class 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 235000021110 pickles Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 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 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- JROURLWMOZCGJV-UHFFFAOYSA-N alizarin blue Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C1=CC=CN=C1C(O)=C2O JROURLWMOZCGJV-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 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
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
- C09B1/06—Preparation from starting materials already containing the anthracene nucleus
- C09B1/14—Dyes containing ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.WPATENT OFFICE W.
In der Patentschrift Nr. 70234 ist ein Verfahren zur Darstellung von neuen Farbstoffen durch Condensation von Anthradichinonen mit Phenolen beschrieben.In patent specification No. 70234 there is a method for the preparation of new dyes described by condensation of anthradichinones with phenols.
Aufser den daselbst angewendeten Anthradichinonen aus Penta- und Hexaoxyanthrachinonen können auch noch andere Anthradichinone, so z. B. die aus Di- und Trioxyalizarinblau darstellbaren Chinone verwendet werden.Except for the anthradichinones from penta- and hexaoxyanthraquinones used there can also other anthradichinones, such. B. those from di- and trioxyalizarin blue representable quinones can be used.
Eines dieser Chinone, und zwar dasjenige, welches aus dem Dioxyalizarinblau (Chinolinderivat des Alizarinbordeaux) der Patentschrift Nr. 58480 entsteht, ist bereits in der Patentschrift Nr. 68113 beschrieben worden. Ein anderes Chinon erhält man, wenn man das Alizarinindigblau der Patentschrift Nr. 47252 z. B. in folgender Weise oxydirt:One of these quinones, namely the one which is derived from dioxyalizarin blue (quinoline derivative des Alizarinbordeaux) of patent specification No. 58480 is already in the patent specification No. 68113. Another quinone is obtained by using the alizarin indig blue Patent Specification No. 47252 e.g. B. oxidized in the following way:
10 kg trockenes Alizarinindigblau werden in 200 kg Schwefelsäure von 66° B. gelöst und bei einer 25 ° nicht übersteigenden Temperatur 5 kg fein gepulverter Braunstein eingetragen. Die Farbe der Lösung geht dabei alltnälig von blau in grün über, und wenn sich keine weitere Aenderung der Farbe mehr bemerkbar macht, giefst man das Reactionsgemisch auf Eis und stumpft die Hauptmenge der Säure durch Zusatz von Alkali ab, so zwar, dafs eine wesentliche Temperaturerhöhung dabei nicht eintritt. Das Chinon scheidet sich ab und kann durch Abfiltriren und Auswaschen mit kaltem Wasser isolirt werden.10 kg of dry alizarin indig blue are dissolved in 200 kg of sulfuric acid of 66 ° B. and at a temperature not exceeding 25 °, 5 kg of finely powdered manganese dioxide were added. The color of the solution changes from blue to green, and if there is no other If the change in color is more noticeable, the reaction mixture is poured onto ice and if the bulk of the acid is blunted by the addition of alkali, it is true that a substantial amount Temperature increase does not occur. The quinone separates and can through Filter off and wash with cold water.
Es zeigt äufserlich grofse Aehnlichkeit mit dem in der Patentschrift Nr. 68113 beschriebenen Derivat aus Dioxyalizarinblau. Es löst sich leicht in verdünnter Schwefelsäure mit rother Farbe; durch Zusatz von schwefliger Säure wird wieder Alizarinindigblau zurückgebildet. Outwardly it shows great resemblance to that described in patent specification No. 68113 Dioxyalizarin blue derivative. It dissolves easily in dilute sulfuric acid with red color; the addition of sulphurous acid reduces the alizarin indig blue.
Die Condensation dieser Chinone aus Oxyalizarinblauderivaten mit Phenolen erfolgt genau in der in dem Haupt-Patent beschriebenen Art und Weise. :The condensation of these quinones from oxyalizarin blue derivatives with phenols is accurate in the manner described in the parent patent. :
Auch hier tritt 1 Molecül des Anthradichinons mit ι Molecül Phenol zusammen, wie aus den erhaltenen Ausbeuten hervorgeht. Am besten vereinigt man die Darstellung des Anthradichinons und die Condensation des letzteren mit dem betreffenden Phenol bezw. substituirten Phenol zu einer einzigen Operation.Here, too, 1 Molecül of the anthradichinone occurs with ι Molecül phenol, as from the obtained yields is evident. It is best to combine the representation of the anthradichinone and the condensation of the latter with the phenol concerned respectively. substituted Phenol to a single operation.
Das Verfahren selbst sei an folgendem Beispiel erläutert.The process itself is explained using the following example.
Farbstoff aus DioxyalizarinblauchinonDioxyalizarin garlicinone dye
und Salicylsäure.and salicylic acid.
10 kg trockenes Dioxyalizarinblau werden in 200 kg Schwefelsäure von 66° B. gelöst und nach der in der Patentschrift Nr. 68113 beschriebenen Methode mit 5 kg Braunstein zu dem Anthradichinon oxydirt. Man trägt hierauf 10 kg Salicylsäure ein, läfst bei einer Temperatur zwischen 20 und 30° circa 18 Stunden10 kg of dry dioxyalizarin blue are dissolved in 200 kg of sulfuric acid of 66 ° B. and according to that in patent specification No. 68113 described method with 5 kg of manganese dioxide oxidized to the anthradichinone. One wears on this 10 kg salicylic acid, takes about 18 hours at a temperature between 20 and 30 °
lang unter öfterem Umrühren stehen, giefst dann in Wasser, filtrirt ab und wäscht neutral.stand for a long time with frequent stirring, then pour into water, filter off and wash neutral.
Der so erhaltene Farbstoff färbt Chrombeizen in blaugrauen Tönen an.The dye thus obtained stains chrome stains in blue-gray tones.
Verwendet man an Stelle des Dioxyalizarin-If one uses instead of the dioxyalizarin
blaus 10,5 kg Alizarinindigblau, so gelangt man zu einem Farbstoff mit den gleichen Färbeeigenschaften.blue 10.5 kg alizarin indig blue, so got result in a dye with the same coloring properties.
In nachstehender Tabelle sind die Eigenschaften einiger dieser Farbstoffe zusammengestellt:The following table summarizes the properties of some of these dyes:
trirter
Schwefel
säureconcen-
trirter
sulfur
acid
Soda
lösungSolution in
soda
solution
lauge
oder
AmmoniakBaking soda
lye
or
ammonia
mit
Thonerde-
beizencoloring
with
Clay
pickle
mit
Chrom
beizenon wool
with
chrome
pickle
Chinon des
Dioxy-
alizarin-
blaus -j-to the
Quinone des
Dioxy
alizarin-
blue -j-
Oxybenzoe'sa'urep-
Oxybenzoic acid
Kresotinsa'ure 0-
Cresotic acid
blaugreenish
blue
blaugreenish
blue
blaus + Salicylsäurethe quinone of the alizarin indig-
blue + salicylic acid
grünbluish
green
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE71306C true DE71306C (en) |
Family
ID=344621
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT71306D Expired - Lifetime DE71306C (en) | Process for the preparation of stain-coloring dyes from anthradichinones and phenols |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE71306C (en) |
-
0
- DE DENDAT71306D patent/DE71306C/en not_active Expired - Lifetime
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