DE47375C - Process for the preparation of blue dyes from a-azonaphtalin-m-amidophenol respectively. the alkyl derivatives thereof - Google Patents
Process for the preparation of blue dyes from a-azonaphtalin-m-amidophenol respectively. the alkyl derivatives thereofInfo
- Publication number
- DE47375C DE47375C DENDAT47375D DE47375DA DE47375C DE 47375 C DE47375 C DE 47375C DE NDAT47375 D DENDAT47375 D DE NDAT47375D DE 47375D A DE47375D A DE 47375DA DE 47375 C DE47375 C DE 47375C
- Authority
- DE
- Germany
- Prior art keywords
- amidophenol
- blue
- dye
- reduction
- azonaphtalin
- 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
- 239000001045 blue dye Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 11
- 230000001603 reducing Effects 0.000 claims description 10
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000003638 reducing agent Substances 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 claims 2
- MBENGEYDAUUYCZ-UHFFFAOYSA-N 1-diazo-2H-naphthalene Chemical compound C1=CC=C2C(=[N+]=[N-])CC=CC2=C1 MBENGEYDAUUYCZ-UHFFFAOYSA-N 0.000 claims 1
- 229920000742 Cotton Polymers 0.000 claims 1
- MFSIEROJJKUHBQ-UHFFFAOYSA-N O.[Cl] Chemical compound O.[Cl] MFSIEROJJKUHBQ-UHFFFAOYSA-N 0.000 claims 1
- VXMKYRQZQXVKGB-CWWHNZPOSA-N Tannin Chemical compound O([C@H]1[C@H]([C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)O[C@H]([C@H]2O)O1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 VXMKYRQZQXVKGB-CWWHNZPOSA-N 0.000 claims 1
- 230000001476 alcoholic Effects 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- YADSGOSSYOOKMP-UHFFFAOYSA-N dioxolead Chemical compound O=[Pb]=O YADSGOSSYOOKMP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- MIMJFNVDBPUTPB-UHFFFAOYSA-N potassium hexacyanoferrate(3-) Chemical compound [K+].[K+].[K+].N#C[Fe-3](C#N)(C#N)(C#N)(C#N)C#N MIMJFNVDBPUTPB-UHFFFAOYSA-N 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 235000018553 tannin Nutrition 0.000 claims 1
- 229920001864 tannin Polymers 0.000 claims 1
- 239000001648 tannin Substances 0.000 claims 1
- 238000010792 warming Methods 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N Hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000007788 liquid Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229940069002 Potassium Dichromate Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 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
- C09B19/00—Oxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Erfindung besteht in der Darstellung violetter, hauptsächlich aber blauer Farbstoffe aus den bei der Combination von a-Diazonaphtalin mit m-Amidophenol bezw. Dimethylm-amidophenol und Diäthyl-m-amidophenol entstehenden Azokörpern.The invention consists in the representation of violet, but mainly blue, dyes from the respectively in the combination of a-diazonaphthalene with m-amidophenol. Dimethylm-amidophenol and diethyl-m-amidophenol resulting azo bodies.
Diese Azokörper liefern bei der Behandlung mit Reductionsmitteln Gemenge von Basen, welche bereits unter dem Einflüsse des Luftsauerstoffes, viel rascher dagegen bei Anwendung von Oxydationsmitteln zu Farbstoffen condensirt werden.When treated with reducing agents, these azo bodies produce mixtures of bases, which are already under the influence of atmospheric oxygen, but much more quickly when used be condensed by oxidizing agents to dyes.
Bei der Reduction der Azokörper, gebildet aus a-Diazonaphtalin und Dimethyl-m-amidophenol bezw. Diäthyl-m-amidophenol entstehen einerseits a-Naphtylamin und andererseits Amidodimethyl bezw. Amidodiäthyl-m-amidophenol. Die beiden letzteren Basen sind in Wasser leicht löslich und bilden mit Säuren äufserst leicht lösliche Salze. Sie zeigen die bemerkenswerthe Eigenschaft, für sich in wässeriger Lösung mit Oxydationsmitteln behandelt, unter Abspaltung von Ammoniak in blaue Farbstoffe überzugehen.In the reduction of the azo bodies formed from a-diazonaphthalene and dimethyl-m-amidophenol respectively Diethyl-m-amidophenol is formed on the one hand a-naphthylamine and on the other hand amidodimethyl respectively Amidodiethyl-m-amidophenol. The latter two bases are in water Easily soluble and form extremely easily soluble salts with acids. They show the remarkable Property, treated by itself in aqueous solution with oxidizing agents, under Elimination of ammonia turns into blue dyes.
Die Reduction der Azoderivate gelingt leicht mit den meisten der üblichen Reductionsmittel. Zweckmäfsig arbeitet man beispielsweise wie folgt:The reduction of the azo derivatives is easy with most of the usual reducing agents. It is useful to work as follows, for example:
20 kg tt-Azonaphtalindiäthyl-m-amidophenol werden in ca. 60 bis 80 kg starker Essigsäure gelöst. Hierauf versetzt man die Lösung mit ca 10 kg Salzsäure und trägt in die intensiv braunroth gefärbte Flüssigkeit so lange Zinkstaub in kleinen Portionen und unter zeitweisem Abkühlen ein, bis die braunrothe Färbung beinahe verschwunden ist, was nach dem Eintragen von ca. 12 bis 14 kg Zinkstaub eintritt. Hierauf setzt man 80 1 Wasser und 20 kg Salzsäure zu, erwärmt einige Zeit' auf ι oo° und filtrirt hierauf von dem .unangegriffenen Zinkstaub ab.20 kg of tt-azonaphthalene diethyl-m-amidophenol are dissolved in approx. 60 to 80 kg strong acetic acid. The solution is then added 10 kg of hydrochloric acid and carries zinc dust into the intensely brown-red colored liquid for a long time in small portions and with occasional cooling until the brown-red The color has almost disappeared, which is evident after adding about 12 to 14 kg of zinc dust entry. 80 liters of water and 20 kg of hydrochloric acid are then added and the mixture is heated for a while ι oo ° and then filtered from the unaffected Zinc dust.
Die Abscheidung und Reindarstellung der Basen aus der Reductionsflüssigkeit ist wegen der grofsen Tendenz, sich bei Gegenwart von Sauerstoff zu Farbstoffen zu condensiren, eine umständliche. Die Isolirung der Basen ist auch gar nicht nöthig, indem es leicht gelingt, die nach der Reduction in Lösung befindlichen Basen direct auf Farbstoffe zu verarbeiten.The separation and purification of the bases from the reduction liquid is because of the great tendency to condense to dyes in the presence of oxygen awkward. The isolation of the bases is also not at all necessary, since it is easy to achieve the to process bases in solution directly on dyes after the reduction.
Bei der Oxydation des Gemisches von Reductionsprodücten, wie es durch Reduction der Azokörper erhalten wird, ist es zu empfehlen, so viel Salzsäure hinzuzufügen, als nöthig ist, um die Basen in Form ihrer neutralen Salze in Lösung zu bringen.In the oxidation of the mixture of reduction products, as it is obtained by reducing the azo bodies, it is advisable to add as much hydrochloric acid as is necessary, to bring the bases into solution in the form of their neutral salts.
Als Oxydationsmittel können verwendet werden: Ferricyanüre, Hypochlorite, Eisenchlorid, Permanganate, Superoxyde, insbesondere aber Chromate.The following can be used as oxidizing agents: ferricyanure, hypochlorite, ferric chloride, Permanganates, super oxides, but especially chromates.
Man verfährt bei der Oxydation zum Beispiel wie folgt:One proceeds with the oxidation, for example, as follows:
Man verdünnt die in der vorher beschriebenen Weise erhaltene Lösung der Reductionsproducte auf ca. 400 1 und versetzt dieselbe so lange nach und nach mit einer Lösung von Kaliumbichromat, welche 10 bis 12 kg des Salzes enthält, bis eine filtrirte Probe der Farbbrühe, auf weiteren Zusatz von Bichromat und daraufThe solution of the reduction products obtained in the manner described above is diluted to approx. 400 1 and gradually add a solution of potassium dichromate to it, which contains 10 to 12 kg of the salt, until a filtered sample of the dye broth, on further addition of bichromate and on it
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE47375C true DE47375C (en) |
Family
ID=322417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT47375D Expired - Lifetime DE47375C (en) | Process for the preparation of blue dyes from a-azonaphtalin-m-amidophenol respectively. the alkyl derivatives thereof |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE47375C (en) |
-
0
- DE DENDAT47375D patent/DE47375C/en not_active Expired - Lifetime
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