DE127532C - - Google Patents
Info
- Publication number
- DE127532C DE127532C DENDAT127532D DE127532DA DE127532C DE 127532 C DE127532 C DE 127532C DE NDAT127532 D DENDAT127532 D DE NDAT127532D DE 127532D A DE127532D A DE 127532DA DE 127532 C DE127532 C DE 127532C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- acid
- dibromoerythrooxyanthraquinone
- color
- sulfuric acid
- 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
- 150000003142 primary aromatic amines Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 150000001454 anthracenes Chemical class 0.000 claims 1
- 239000001045 blue dye Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N Solvent Violet 13 Chemical class C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Vr 127532 KLASSE 22b. Vr 127532 CLASS 22b.
In der Patentschrift 114199 ist gezeigt, dafs, wenn man primäre aromatische Amine mit Monohalogenchinizarin in Reaction bringt, zunächst das in β - Stellung befindliche Halogen gegen den Alphylidorest ausgetauscht wird.The patent specification 114199 shows that when primary aromatic amines are brought into reaction with monohaloquinizarine, first the halogen in the β position is exchanged for the alphylido radical.
Es wurde nun gefunden, dafs bei Einwirkung von Aminen auf Dibromerythrooxyanthrachinon It has now been found that the action of amines on dibromoerythrooxyanthraquinone
OH CO. i Br OH CO. i Br
also auf ein Product, welches die negativen Gruppen in denselben Stellungen enthält, wie das oben erwähnte Halogenchinizarin, im Gegensatz zu dem oben genannten Reactionsverlauf nicht das in β-Stellung, sondern das in α - Stellung befindliche Bromatom gegen den Alphylidorest ausgetauscht wird. Man gelangt auf diese Weise zu einem bromirten Chinizarinblau: thus on a product which contains the negative groups in the same positions as the haloquinizarin mentioned above, in contrast to the course of the reaction mentioned above not the one in the β position, but the bromine atom in the α position against the Alphylidorest is exchanged. One arrives at a brominated quinizarin blue in this way:
OHOH
NHR.NHR.
Das erwähnte Dibromerythrooxyanthrachinon kann erhalten werden durch Einwirkung von Brom auf Erythrooxyanthrachinonsulfosäure. Man erhitzt z. B. 10 kg erythrooxyanthrachinonsulfosaures Natron mit 30 kg Wasser und 10 kg Brom 12 Stunden im Autoclaven auf 120 bis 1300. Das Dibromid scheidet sich dabei in rothgelben Nadeln aus, die bei 2330 schmelzen. Es löst sich in concentrirter Schwefelsäure mit braunrother Farbe, die auf Zusatz von Borsäure bedeutend röther wird. In Natronlauge ist es mit rother Farbe löslich.The aforementioned dibromoerythrooxyanthraquinone can be obtained by the action of bromine on erythrooxyanthraquinone sulfonic acid. One heated z. B. 10 kg of erythrooxyanthraquinonesulfosaures soda with 30 kg of water and 10 kg of bromine for 12 hours in the autoclave to 120 to 130 0 . The dibromide separates out in red yellow needles which melt at 233 0th It dissolves in concentrated sulfuric acid with a brownish-red color, which becomes considerably redder on the addition of boric acid. It is soluble in caustic soda with a red color.
Zur Darstellung von Bromchinizarinblau verfährt man folgendermafsen:To display bromquinizarin blue, proceed as follows:
10 kg Erythrooxyanthrachinondibromid werden mit 100 kg p-Toluidin auf 80 bis ioo° erwärmt, bis eine Probe der Schmelze sich in Chloroform mit blauer Farbe löst. Die Aufarbeitung der Schmelze geschieht in bekannter Weise. Der Farbstoff wird durch Umkrystallisiren aus Eisessig in blauen Nadeln erhalten, welche sich in Schwefelsäure mit grüner, in Anilin mit blauer Farbe lösen. Auf Zusatz von Borsäure zur schwefelsauren Lösung geht die Farbe in Blau über.10 kg of erythrooxyanthraquinone dibromide are increased to 80 ° to 100 ° with 100 kg of p-toluidine heated until a sample of the melt dissolves in chloroform with a blue color. The work-up the melt takes place in a known manner. The dye is crystallized by recrystallization obtained from glacial acetic acid in blue needles, which are dissolved in sulfuric acid with green, in Dissolve aniline with blue color. On the addition of boric acid to the sulfuric acid solution goes the color in blue over.
Durch Erwärmen mit Schwefelsäuremonohydrat auf ioo° geht das Product in seine Sulfosäure über, welche Wolle in saurem Bade in schönen, blauen, echten Tönen anfärbt; aufBy heating with sulfuric acid monohydrate to 100 ° the product goes into its Sulphonic acid, which in an acid bath dyes wool in beautiful, blue, genuine tones; on
chromgebeizter Wolle erhält man schöne, grünblaue Nuancen.chrome-stained wool gives beautiful, green-blue nuances.
Ganz analoge Farbstoffe erhält man, wenn man an Stelle des p-Toluidins andere primäre aromatische Amine auf Dibromerythrooxyanthrachinon einwirken läfst. Man erhält hierbei Producte, welche durch Sulfiren werthvolle blaufärbende Farbstoffsulfosäuren liefern.Completely analogous dyes are obtained if other primary ones are used instead of p-toluidine allows aromatic amines to act on dibromoerythrooxyanthraquinone. One obtains here Products which, by sulphurisation, give valuable blue-coloring dye sulphonic acids.
Claims (1)
Verfahren zur Darstellung von blauen Farbstoffen der Anthracenreihe, darin bestehend, dafs man statt der im Verfahren des Patentes 114199 (Zusatz zum Patent 86150) verwendeten Halogenchinizarine hier Dibromerythrooxyanthrachinon mit primären aromatischen Aminen condensirt.Patent claim:
Process for the preparation of blue dyes of the anthracene series, consisting in condensing dibromoerythrooxyanthraquinone with primary aromatic amines instead of the haloquinizarines used in the process of patent 114199 (addition to patent 86150).
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE127532C true DE127532C (en) |
Family
ID=396116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT127532D Active DE127532C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE127532C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2624746A (en) * | 1950-01-27 | 1953-01-06 | Eastman Kodak Co | Nuclear monohalogenated 1-hydroxy-4-beta-fluoroalkylaminoanthraquinone compounds andprocess for their preparation |
-
0
- DE DENDAT127532D patent/DE127532C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2624746A (en) * | 1950-01-27 | 1953-01-06 | Eastman Kodak Co | Nuclear monohalogenated 1-hydroxy-4-beta-fluoroalkylaminoanthraquinone compounds andprocess for their preparation |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE127532C (en) | ||
| DE412122C (en) | Process for the preparation of Kuepen dyes | |
| DE2902485A1 (en) | 6/7 HALOGEN-ANTHRACHINONE COMPOUNDS, THEIR PRODUCTION AND USE | |
| DE127341C (en) | ||
| DE116546C (en) | ||
| DE210828C (en) | ||
| DE127814C (en) | ||
| DE362457C (en) | Process for the production of sulfur-containing Kuepen dyes | |
| DE131873C (en) | ||
| DE290064C (en) | ||
| DE128753C (en) | ||
| DE85885C (en) | ||
| DE516784C (en) | Process for the preparation of Kuepen dyes of the 1íñ2-Benzanthraquinone series | |
| DE507236C (en) | Process for the production of acid dyes of the rhodamine series | |
| DE86415C (en) | ||
| DE126392C (en) | ||
| DE108546C (en) | ||
| DE86222C (en) | ||
| DE121228C (en) | ||
| DE288825C (en) | ||
| DE148767C (en) | ||
| DE127438C (en) | ||
| DE137078C (en) | ||
| DE120266C (en) | ||
| DE282502C (en) |