DE232262C - - Google Patents
Info
- Publication number
- DE232262C DE232262C DENDAT232262D DE232262DA DE232262C DE 232262 C DE232262 C DE 232262C DE NDAT232262 D DENDAT232262 D DE NDAT232262D DE 232262D A DE232262D A DE 232262DA DE 232262 C DE232262 C DE 232262C
- Authority
- DE
- Germany
- Prior art keywords
- blue
- red
- aminoanthraquinone
- green
- nitro
- 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
- 230000001476 alcoholic Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- IVNZBWNBYXERPK-DZGBHZPSSA-K trisodium;(8Z)-7-oxo-8-[(4-sulfonatonaphthalen-1-yl)hydrazinylidene]naphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N\N=C3/C(=O)C=CC=4C=C(C=C(C=43)S([O-])(=O)=O)S(=O)(=O)[O-])=CC=C(S([O-])(=O)=O)C2=C1 IVNZBWNBYXERPK-DZGBHZPSSA-K 0.000 description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- -1 6-nitrochloroanthraquinone Chemical compound 0.000 description 1
- LMTSAKNFSGDUQC-UHFFFAOYSA-N BrCNC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound BrCNC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O LMTSAKNFSGDUQC-UHFFFAOYSA-N 0.000 description 1
- 241000131971 Bradyrhizobiaceae Species 0.000 description 1
- 240000000358 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- WQZQXBXIUMKNCK-UHFFFAOYSA-N [S].OB(O)O Chemical compound [S].OB(O)O WQZQXBXIUMKNCK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000011734 sodium 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
- 239000000984 vat dye 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
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 232262 -KLASSE 22 b. GRUPPE - JVl 232262 - CLASS 22 b. GROUP
Verfahren zur Darstellung von Alkoxyanthrimiden. Patentiert im Deutschen Reiche vom 17. März 1909 ab. Process for the preparation of alkoxyanthrimides. Patented in the German Empire on March 17, 1909.
Behandelt man negativ substituierte Anthrimide mit alkoholischem Alkali, so tritt Substitution der negativen Gruppen durch den Alkoxylrest ein und man gelangt zu den als Küpenfarbstoffen oder als Ausgangsmaterialien zu solchen Farbstoffen wichtigen Alkoxyanthrimiden. If negatively substituted anthrimides are treated with alcoholic alkali, substitution occurs the negative groups through the alkoxyl radical and one arrives at the as Vat dyes or alkoxyanthrimides important as starting materials for such dyes.
Da beispielsweise beim p-Nitro-a-aminoanthrachinon, Brommethylaminoanthrachinon undSince, for example, p-nitro-a-aminoanthraquinone, bromomethylaminoanthraquinone and
ίο ähnlichen Körpern eine Substitution durch die Alkoxylgruppe nicht gelingt, so war es um so überraschender, daß der Austausch bei so hoch molekularen und schwer löslichen Körpern wie den Anthrimiden so glatt erfolgte. Es. ist nach diesem Verfahren möglich, auch zu neuen Alkoxyanthrimiden zu gelangen, welche auf andere Weise nicht zugänglich sind.ίο similar bodies a substitution by the If the alkoxyl group fails, it was all the more surprising that the exchange was so high molecular and sparingly soluble bodies like the anthrimids took place so smoothly. It. is possible by this process to arrive at new alkoxyanthrimides, which on inaccessible any other way.
Zu den als Ausgangsmaterialien dienenden negativ substituierten Anthrimiden gelangt manThe negatively substituted anthrimides used as starting materials are obtained
z. B. durch Halogenisierung bzw. Nitrierung der Anthrimide oder durch Kondensation von Nitrohalogenanthrachinonen mit Aminoanthrachinonen. z. B. by halogenation or nitration of the anthrimides or by condensation of nitrohalogenanthraquinones with aminoanthraquinones.
5 Teile des Kondensationsproduktes aus ι · 6-Nitrochloranthrachinon mit i-Aminoanthrachinon werden im Autoklaven mit einer Lösung von 5 Teilen Ätzkali in 50 Teilen Methylalkohol 5 Stunden auf ioo° erhitzt. Nach dem Abkühlen saugt man das erhaltene Produkt ab, wäscht mit etwas Methylalkohol und dann mit Wasser und trocknet. Man erhält so ein braunrotes Pulver, das sich in Schwefelsäure olive löst, und das beim Eingießen dieser Lösung in Wasser in ziegelroten Flocken ausfällt. In der Küpe wird ungebeizte Baumwolle bordeauxrot angefärbt.5 parts of the condensation product of ι · 6-nitrochloroanthraquinone with i-aminoanthraquinone are in the autoclave with a solution of 5 parts of caustic potash in 50 parts of methyl alcohol Heated to 100 ° for 5 hours. After cooling, the product obtained is filtered off with suction off, wash with a little methyl alcohol and then with water and dry. A brown-red powder is obtained in this way, which is dissolved in sulfuric acid olive dissolves, and that precipitates in brick-red flakes when this solution is poured into water. Unstained cotton is dyed claret-red in the vat.
5 Teile ,des Kondensationsproduktes aus ι -Nitro-4-aminoanthrachinon mit £-Chloranthrachinon werden mit 75 Teilen Pyridin und 20 Teilen Natriummethylat (10 g Na in 100 ecm) am Rückflußkühler gekocht. Nach Y2 bis ι Stunde läßt man erkalten, verdünnt mit dem gleichen Volumen Wasser, saugt ab und wäscht mit etwas Alkohol und dann mit Wasser. Nach dem Trocknen erhält man ein dunkelviolettes Pulver, das sich in Schwefelsäure grünblau löst und beim- Eingießen dieser Lösung in Wasser in bordeauxfarbenen Flocken ausfällt. Ungebeizte Baumwolle wird in der Küpe in violettroten Tönen angefärbt.5 parts of the condensation product of ι -nitro-4-aminoanthraquinone with ε -chloranthraquinone are refluxed with 75 parts of pyridine and 20 parts of sodium methylate (10 g of Na in 100 ecm). After 2 to ι hours, the mixture is allowed to cool, diluted with the same volume of water, filtered off with suction and washed with a little alcohol and then with water. After drying, a dark violet powder is obtained which dissolves green-blue in sulfuric acid and precipitates in burgundy flakes when this solution is poured into water. Unstained cotton is dyed in the vat in purple-red tones.
Behandelt man in der in Beispiel 2 beschriebenen Weise Brom-a-ß-dianthrachinonylamin — erhalten durch Einwirkung von überschüssigem Brom auf «-ß-Dianthrachinonyl-. amin in verdünnter Schwefelsäure bei 80 ° —■, so resultiert ein dem obigen sehr ähnliches Produkt, das sich in Schwefelsäure grünblau löst und beim Eingießen dieser Lösung inIf you treat bromo-α-ß-dianthraquinonylamine in the manner described in Example 2 - obtained by the action of excess bromine on «-ß-dianthraquinonyl-. amine in dilute sulfuric acid at 80 ° - ■, the result is a product very similar to the above, which dissolves green-blue in sulfuric acid and when this solution is poured into
Wasser in bordeauxfarbenen Flocken ausfällt, j Die Eigenschaften einiger nach diesem Ver-Water precipitates in burgundy flakes, j the properties of some according to this
Ungebeizte Baumwolle wird in violettroten Tönen angefärbt.Unstained cotton is dyed in purple-red tones.
Ganz analog verhalten sich auch andere 5 negativ substituierte Anthrimide.The other 5 negatively substituted anthrimides also behave in a completely analogous manner.
fahren erhältlichen Alkoxyanthrimide sowie 40
deren Ausgangsmaterialien sind aus folgender
Tabelle ersichtlich.drive available alkoxyanthrimides and 40 their starting materials are from the following
Table.
Pyridinin
Pyridine
konzen
trierter
Schwefel
säurein
concentrate
trotter
sulfur
acid
Schwefel
borsäure
bei gelindem
Erwärmenin
sulfur
boric acid
at the slightest
Heat
Schwefel
säure
+
Formaldehydin
sulfur
acid
+
formaldehyde
auf
Baumwollecoloring
on
cotton
+ i-Aminoanthrachinonι -nitro -6- chloranthraquinone
+ i-aminoanthraquinone
+ 2-Chloranthrachinonι-nitro-4-aminoanthraquinone
+ 2-chloroanthraquinone
aminBromo-a-ß-dianthraquinonyl-
amine
schwer
löslichyellow-brown,
heavy
soluble
Rotbrownish
Red
+ i-Aminoanthrachinon
mit methylalkoholischem Kali
behandeltι -nitro-6-chloroanthraquinone
+ i-aminoanthraquinone
with methyl alcoholic potash
treated
graublaublue
gray-blue
grün ■. green
green ■
+ 2-Chloranthrachinon
mit Methylat behandeltι-nitro-4-aminoanthraquinone
+ 2-chloroanthraquinone
treated with methylate
mit Methylat behandeltBromo-α-β-dianthraquinonylamine
treated with methylate
Claims (1)
Publications (1)
Publication Number | Publication Date |
---|---|
DE232262C true DE232262C (en) |
Family
ID=492300
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DENDAT232262D Active DE232262C (en) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE232262C (en) |
-
0
- DE DENDAT232262D patent/DE232262C/de active Active
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