DE110880C - - Google Patents
Info
- Publication number
- DE110880C DE110880C DE1899110880D DE110880DA DE110880C DE 110880 C DE110880 C DE 110880C DE 1899110880 D DE1899110880 D DE 1899110880D DE 110880D A DE110880D A DE 110880DA DE 110880 C DE110880 C DE 110880C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- blue
- solution
- spectrum
- monosulfonic
- 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
- 239000002253 acid Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 3
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical class O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 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 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L Iron(II) chloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229940069002 Potassium Dichromate Drugs 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 description 1
- 239000003830 anthracite Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 239000002966 varnish 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/52—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated
- C09B1/521—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated unsubstituted amino and hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom 7. Februar 1899 ab.Patented in the German Empire on February 7, 1899.
In dem Patent 108578 sind neue Reductionsproducte der Diamidochrysazin- bezw. anthrarufjndisulfosäure beschrieben, welche den Charakter von Leukoverbindungen haben. Diese lassen sich, wie gefunden wurde, leicht und quantitativ durch Oxydation in die Diamidoanthrarufinbezw. Diamidochrysazinmonosulfosäure überführen.In the patent 108578 are new reduction products of Diamidochrysazin- bezw. anthrarufic disulfonic acid described, which have the character of leuco compounds. As has been found, these can be easily and quantitatively by oxidation into the Diamidoanthrarufinbezw. Diamidochrysazine monosulfonic acid convict.
Das Verfahren besteht im Allgemeinen darin, dafs die Leukoverbindungen in alkalischer, neutraler oder saurer Lösung mit Oxydationsmitteln, wie concentrirter Schwefelsäure, Kaliumbichromat, Eisenchlorid, Sauerstoff etc., behandelt werden.The process consists in general in that the leuco compounds in alkaline, neutral or acidic solution with oxidizing agents, such as concentrated sulfuric acid, potassium dichromate, Ferric chloride, oxygen, etc., can be treated.
Beispiel 1.Example 1.
10 kg der nach Beispiel 1 des Patentes 108578 erhaltenen Leukoverbindung I aus Diamidoanthrarufindisulfosäure werden in 500 1 Wasser und 50 kg Natronlauge von 300 B. gelöst. Man leitet nun einen kräftigen Luftstrom ein, worauf die Lösung eine intensiv blaue Farbe annimmt. Während der Operation scheidet sich das Natronsalz der Diamidoanthraruönmonosulfosäure zum gröfsten Theil aus, durch Zusatz von Säuren wird das Reactionsproduct vollständig gefällt. Die so erhaltene Monosulfosäure stellt in feuchtem Zustande eine violette Paste, trocken ein dunkles Pulver dar. Sie löst sich sehr schwer in heifsem Wasser mit blauer Farbe. Auf Zusatz von Natronlauge erhält man eine intensiv blaue Lösung. Concentrirte Schwefelsäure nimmt das Product mit gelber Farbe auf. Auf Zusatz von Borsäure wird die letztere Lösung erst roth, dann blau und zeigt ein Spektrum, das aus zwei Linien in Gelb und Grün besteht und gegen das Spectrum der Diamidoanthrarufindisulfosäure gegen Blau verschoben erscheint. Auf ungeheizter Wolle erhält man schöne blaue Töne, auf vorchromirter Wolle ein grüneres Blau.10 kg of the leuco compound obtained according to Example 1 of the patent 108 578 I from Diamidoanthrarufindisulfosäure are dissolved in 500 1 of water and dissolved 50 kg of sodium hydroxide solution of 30 0 B.. A vigorous stream of air is then introduced, whereupon the solution takes on an intense blue color. During the operation the sodium salt of diamido anthracite monosulfonic acid is for the most part precipitated, and the product of the reaction is completely precipitated by the addition of acids. The monosulfonic acid thus obtained is a violet paste when moist, and a dark powder when dry. It is very difficult to dissolve in hot water with a blue color. When adding sodium hydroxide solution, an intensely blue solution is obtained. Concentrated sulfuric acid picks up the product with a yellow color. When boric acid is added, the latter solution turns first red, then blue, and shows a spectrum which consists of two lines in yellow and green and which appears shifted from the spectrum of diamidoanthrarufin disulfonic acid towards blue. Nice blue tones are obtained on unheated wool, and a greener blue on pre-chromed wool.
' Man löst 10 kg der in Beispiel 2 des Patentes 108578 beschriebenen Leukoverbindung II der Diamidoanthrarufinmonosulfosäure in 200 kg 66° Schwefelsäure und erhitzt die Schmelze auf 60 bis 700. Unter Entbindung von schwefliger Säure vollzieht sich in kurzer Zeit die Oxydation. Sobald eine Probe auf Zusatz von Borsäure nicht mehr grün, sondern rein blau gefärbt erscheint, giefst man das Reactionsgemisch in Wasser, wobei sich die Monosulfosäure als violetter Niederschlag unlöslich abscheidet.'Dissolve 10 of the leuco compound II described in Example 2 of the patent 108578 kg of Diamidoanthrarufinmonosulfosäure in 200 kg of sulfuric acid 66 ° and the melt is heated to 60 to 70 0th Oxidation takes place in a short time with the release of sulphurous acid. As soon as a sample no longer appears green but pure blue after the addition of boric acid, the reaction mixture is poured into water, the monosulfonic acid separating out insoluble as a violet precipitate.
ι ο kg Leukodiamidochrysazinmonosulfosäure II werden in 500 1 Wasser gelöst und unter lebhaftem Umrühren die berechnete Menge Eisenchlorid in verdünnter wässeriger Lösung zugesetzt. Es entsteht alsbald eine rein blaue Lösung, die bei' weiterem Stehen und Zusatz von wenig Säure die Diamidochrysazinmonosulfosä'ure als krystallinischen Niederschlag absetzt. Man filtrirt, wäscht mit angesäuertem Wasser und trocknet. Das so erhaltene Product verhält sich dem Anthrarufinderivat (Beispiel 1) ganz analog. Die gelbe Lösung in Schwefelsäure . wird aber 'durch Zusatz vonι ο kg leukodiamidochrysazine monosulfonic acid II are dissolved in 500 l of water and the calculated amount of iron chloride while stirring vigorously added in dilute aqueous solution. A pure blue solution arises immediately, which with further standing and addition the diamidochrysazine monosulfonic acid separates from a little acid as a crystalline precipitate. It is filtered and washed with acidified Water and dry. The product obtained in this way behaves like the anthrarufin derivative (example 1) completely analog. The yellow solution in sulfuric acid. but becomes' by adding
Borsäure kaum verändert. Dagegen erhält man beim Erwärmen des Farbstoffes mit Monohydrat und Borsäure eine schwach violett gefärbte Lösung, die ein charakteristisches Spektrum zeigt. Mit dem analog erhaltenen Spektrum der Diamidochrysazindisulfosäure verglichen, erscheint es nach dem brechbareren Theil des Spektrums verschoben. Die Färbungen auf ungeheizter und chromgebeizter Wolle sind von denen des Anthrarufinderivates nicht zu unterscheiden.Boric acid hardly changed. In contrast, when the dye is heated with monohydrate, it is obtained and boric acid a pale purple colored solution that has a characteristic spectrum shows. Compared with the spectrum of diamidochrysazine disulphonic acid obtained analogously, it appears shifted towards the more frangible part of the spectrum. The colorations on unheated and chrome-stained wool are different from those of the anthrarufine derivative differentiate.
Claims (1)
Verfahren zur Darstellung ' von Diamidoanthrarufinbezw. Diamidochrysazinmonosulfosäure, darin bestehend, dafs man die in dem Patent 108578 beschriebenen Leukoverbindungen mit Oxydationsmitteln behandelt.Patent claim: .., ■,
Process for the preparation of 'Diamidoanthrarufinbezw. Diamidochrysazine monosulfonic acid, consisting in treating the leuco compounds described in patent 108578 with oxidizing agents.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT4939D AT4939B (en) | 1899-02-06 | 1900-03-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE110880C true DE110880C (en) |
Family
ID=380665
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1899110880D Expired - Lifetime DE110880C (en) | 1899-02-06 | 1899-02-06 |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE110880C (en) |
-
1899
- 1899-02-06 DE DE1899110880D patent/DE110880C/de not_active Expired - Lifetime
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