DE62505C - Process for the representation of dyes from Alizarin-Bordeaux and its ana lies. (2 - Google Patents
Process for the representation of dyes from Alizarin-Bordeaux and its ana lies. (2Info
- Publication number
- DE62505C DE62505C DENDAT62505D DE62505DA DE62505C DE 62505 C DE62505 C DE 62505C DE NDAT62505 D DENDAT62505 D DE NDAT62505D DE 62505D A DE62505D A DE 62505DA DE 62505 C DE62505 C DE 62505C
- Authority
- DE
- Germany
- Prior art keywords
- bordeaux
- alizarin
- sulfuric acid
- dyes
- water
- 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
- 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 title claims description 7
- 238000000034 method Methods 0.000 title claims 5
- 239000000975 dye Substances 0.000 title description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 17
- 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
- RDFLLVCQYHQOBU-GPGGJFNDSA-O Cyanin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@H](CO)O1)c1c(-c2cc(O)c(O)cc2)[o+]c2c(c(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O3)cc(O)c2)c1 RDFLLVCQYHQOBU-GPGGJFNDSA-O 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M CHEMBL593252 Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000000875 corresponding Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000003086 colorant Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 11
- 210000002268 Wool Anatomy 0.000 description 7
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N Manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- -1 cyanine sulfonic acids Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 238000005406 washing 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
- C09B1/02—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)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In dem Patent No. 62018 ist das sogenannte Alizarincyanin beschrieben, jener werthvolle Farbstoff, welcher aus Alizarin-Bordeaux durch Oxydation in schwefelsaurer Lösung erhalten wird. Aehnliche Farbstoffe bilden den Gegenstand des ersten Zusatz-Patentes No. 62504, nämlich diejenigen Producte, welche durch Oxydation der aus Flavo- und Anthrapurpurin gewonnenen Bordeaux' in schwefelsaurer Lösung entstehen.In patent no. 62018 the so-called alizarin cyanine is described, that valuable one Dye obtained from Alizarin-Bordeaux by oxidation in a sulfuric acid solution will. Similar dyes are the subject of the first additional patent no. 62504, namely, those products which, by the oxidation of flavo- and anthrapurpurine obtained Bordeaux 'arise in sulfuric acid solution.
Die in diesen beiden Patenten beschriebenen Alizarinfarbstoffe, von denen der aus Alizarin-Bordeaux gewonnene sich unter dem Namen »Alizarincyanin R« im Handel befindet, lassen sich leicht in Sulfosäuren überführen, wenn man sie mit rauchender Schwefelsäure oder deren Ersatzmitteln behandelt. Die so zu erhaltenden Cyaninsulfosäuren besitzen vor den Cyaninen den Vorzug der leichten Löslichkeit in Wasser und sind deshalb als wasserlösliche Wollfarbstoffe von besonders grofsem Werthe.The alizarin dyes described in these two patents, of which that from Alizarin-Bordeaux obtained under the name "Alizarincyanin R" is in the trade easily converted into sulphonic acids if they are mixed with fuming sulfuric acid or their substitutes treated. The cyanine sulfonic acids to be obtained in this way have before the Cyanines have the advantage of being readily soluble in water and are therefore considered water-soluble Wool dyes of especially great value.
Zur Darstellung des Farbstoffes aus Alizarincyanin R verfährt man z. B. in folgender Weise:To prepare the dye from Alizarincyanin R one proceeds z. B. in the following Way:
ι ο kg trockenes Alizarincyanin R werden mit 35 kg rauchender Schwefelsäure von 20 pCt. Anhydridgehalt auf 100 bis 1200 erhitzt, bis eine Probe des Gemisches in Wasser sich klar auflöst.ι ο kg of dry Alizarincyanin R with 35 kg of fuming sulfuric acid of 20 pCt. Anhydride content heated to 100 to 120 0 until a sample of the mixture dissolves clearly in water.
Man giefst dann in Wasser, salzt aus, filtrirt, preist und trocknet.It is then poured into water, salted out, filtered, priced and dried.
In gleicher Weise gelangt man zu den Sulfosäuren der Cyanine aus Flavo- und Anthrapurpurin-Bordeaux. In the same way one arrives at the sulfonic acids of the cyanines from flavo- and anthrapurpurin-Bordeaux.
Diese Cyaninsulfosäuren sind sämmtlich in Wasser leicht mit prächtig rother, in Natronlauge mit blauer Farbe löslich. Auf mit Thonerde vorgebeizter Wolle erzeugen sie ein sehr schönes Violett, auf chromirter Wolle ein ebenso schönes Blau.These cyanine sulfonic acids are all light in water with a splendid red color in caustic soda soluble with blue color. On wool pre-stained with clay they produce a very beautiful violet, on chromed wool an equally beautiful blue.
Es hat sich ferner gezeigt, dafs die bei der Oxydation der Bordeaux' zu den entsprechenden Cyaninen auftretenden, bereits in den oben genannten beiden Patenten erwähnten, leicht zersetzlichen Zwischenproducte eine grofse technische Bedeutung besitzen, da sie sowohl direct zum Färben und Drucken verwendet, als auch bei der Einwirkung gewisser Substanzen (wie z. B. Ammoniak) in neue Farbstoffe übergeführt werden können.It has also been shown that those in the oxidation of the Bordeaux 'correspond to the corresponding Cyanines, which are already mentioned in the two patents mentioned above, are easily decomposable intermediate products have technical importance, since they are used both directly for dyeing and printing, as well as the action of certain substances (such as ammonia) in new dyes can be transferred.
Um beispielsweise das Alizarincyaninzwischenproduct darzustellen, verfährt man am besten wie folgt:For example, the best approach is to represent the alizarin cyanine intermediate as follows:
10 kg Alizarin-Bordeaux werden in 200 kg Schwefelsäure von 66 ° B. gelöst und mit 12 kg Braunstein in der im Patent No. 62018 angegebenen Weise oxydirt. Durch gute Kühlung trägt man dafür Sorge, dafs die Temperatur des Oxydationsgemisches 30 bis 40° C. nicht übersteigt, da das Zwischenpro duct bei höherer Temperatur bereits Zersetzung erleidet. Die Reaction ist als beendet anzusehen,10 kg of Alizarin-Bordeaux become 200 kg Sulfuric acid of 66 ° B. dissolved and mixed with 12 kg of manganese dioxide in the patent no. 62018 oxidized in the manner indicated. Good cooling ensures that the temperature of the oxidation mixture is 30 to Does not exceed 40 ° C., since the intermediate product already undergoes decomposition at a higher temperature. The reaction is to be regarded as ended,
wenn eine 'mit. concentrirter Schwefelsäure verdünnte Probe im durchfallenden Licht nicht mehr violett, sondern rein blau erscheint. Das Gemisch wird hierauf unter Vermeidung jeder Temperaturerhöhung in Eiswasser gegossen, . wobei sich das Zwischenproduct in dunkelvioletten, Flocken abscheidet, welche abfiltrirt und möglichst schnell so lange mit Eiswasser gewaschen werden, bis das Waschwasser anfängt, violett gefärbt abzulaufen. So dargestellt, bildet das Zwischenprodnct einen dunkelvioletten Niederschlag, welcher in Wasser mit "violetter Farbe löslich ist. ·if one 'with. concentrated sulfuric acid does not dilute the sample in transmitted light appears more purple but pure blue. The mixture is hereupon avoiding any Temperature increase poured into ice water,. the intermediate product separates out in dark purple flakes, which are filtered off and washed with ice water as quickly as possible until the washing water starts, purple colored expire. So represented, the intermediate product forms a dark purple precipitate, which in water with "is soluble in violet color. ·
In Alkohol ist das Zwischenproduct leicht mit violetter, in concentrirter Schwefelsäure, wie das Alizarincyanin R, mit blauer Farbe löslich; r"·" " ■ -' ■·■·>■-■·'■■ ■ ■■In alcohol the intermediate product is easily mixed with violet, in concentrated sulfuric acid, like Alizarincyanin R, soluble in blue color; r "·" "■ - '■ · ■ ·> ■ - ■ ·' ■■ ■ ■■
Dagegen besitzt die schwefelsaure Lösung des Zwischenproductes nicht die für das Alizarincyanin R charakteristische zinnoberrothe Fluorescenz. Mit Thonerde vorgebeizte Wolle färbt es violett, chromgebeizte Wolle dagegen blau an.On the other hand, the sulfuric acid solution of the intermediate product does not have the vermilion red characteristic of Alizarincyanin R. Fluorescence. Wool pre-stained with clay it dyes purple, while chrome-stained wool blue on.
Zu analogen Zwischenproducten gelangt man auch, indem man Flavo- und Anthrapurpurin-Bordeaux des Patentes No.. 60855, m concentrirter Schwefelsäure gelöst, mit Oxydationsmitteln, wie z. B. Braunstein, in der oben beschriebenen Weise behandelt.Analogous intermediate products can also be obtained by dissolving flavo- and anthrapurpurin-Bordeaux of Patent No. 60855, m concentrated sulfuric acid, with oxidizing agents, such as, for. B. Brownstone, treated in the manner described above.
Die so zu erhaltenden Producte ähneln dem' Alizarin-Bordeaux darstellbaren in jederThe products to be obtained in this way resemble the 'Alizarin-Bordeaux that can be represented in every one
Beziehung und erzeugen auf mit Thonerde vorgebeizter Wolle violette, auf chromgebeizter Wolle blaue Töne.Relationship and produce violet on wool pre-stained with alumina, and on chrome-stained wool Wool blue tones.
Diese Zwischenproducte lassen sich leicht, und zwar durch Kochen ihrer wässerigen Lösungen für sich oder unter Zusatz von Schwefel- bezw. Salzsäure in die entsprechen-.These intermediate products can easily be made watery by boiling them Solutions by themselves or with the addition of sulfur or. Hydrochloric acid in the corresponding.
den Cyanine überführen. Behufs Umwandlung des bei der Oxydation von Alizarin - Bordeaux in schwefelsaurer Lösung mittelst Braunsteins erhaltenen Zwischenproductes in Alizarincyanin R verfährt man in der Weise, dafs man das·, wie oben angegeben, durch Eingiefsen der Reactionsmasse in Eiswasser erhaltene Gemisch so lange zum Sieden erhitzt, bis die Farbe des Niederschlages von violett in rothbraun übergegangen ist.transfer the cyanine. For the purpose of transforming that in the oxidation of Alizarin - Bordeaux Intermediate products obtained in alizarin cyanine in sulfuric acid solution by means of brown stone R one proceeds in such a way that the the reaction mixture obtained in ice water is heated to boiling until the color of the precipitate turns violet in has gone red-brown.
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE62505C true DE62505C (en) |
Family
ID=336487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT62505D Expired - Lifetime DE62505C (en) | Process for the representation of dyes from Alizarin-Bordeaux and its ana lies. (2 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE62505C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146722A (en) * | 1960-01-19 | 1964-09-01 | Res & Dev Pty Ltd | Centrifugal pumps and the like |
| US3265002A (en) * | 1961-01-13 | 1966-08-09 | Res & Dev Pty Ltd | Centrifugal pumps and the like |
-
0
- DE DENDAT62505D patent/DE62505C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3146722A (en) * | 1960-01-19 | 1964-09-01 | Res & Dev Pty Ltd | Centrifugal pumps and the like |
| US3265002A (en) * | 1961-01-13 | 1966-08-09 | Res & Dev Pty Ltd | Centrifugal pumps and the like |
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