CH224875A - Process for the preparation of a new, water-soluble dye of the anthraquinone series. - Google Patents
Process for the preparation of a new, water-soluble dye of the anthraquinone series.Info
- Publication number
- CH224875A CH224875A CH224875DA CH224875A CH 224875 A CH224875 A CH 224875A CH 224875D A CH224875D A CH 224875DA CH 224875 A CH224875 A CH 224875A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- new
- mol
- preparation
- soluble dye
- Prior art date
Links
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004043 dyeing Methods 0.000 claims description 4
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 3
- OZGQBYYIBKKSRJ-UHFFFAOYSA-N 1,4-diamino-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC(N)=C3C(=O)C2=C1 OZGQBYYIBKKSRJ-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 235000005811 Viola adunca Nutrition 0.000 claims description 3
- 240000009038 Viola odorata Species 0.000 claims description 3
- 235000013487 Viola odorata Nutrition 0.000 claims description 3
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 2
- 229940081735 acetylcellulose Drugs 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution 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
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Terfahren zur Darstellung eines neuen, wasserlöslichen Farbstoffes der Anthrachinonreihe. Das vorliegende Patent betrifft ein Ver fahren zur Darstellung eines neuen, wasser löslichen Farbstoffes der Anthrachinonreihe und ist dadurch gekennzeichnet, dass man 1 Mol 1,4-Diamino-2-methylanthrachinon, 1. Mol Phenol und 1 Mol Formaldehyd auf einander einwirken lässt und das erhaltene Produkt sulfoniert.
Der neue Farbstoff enthält 1 Sulfogruppe und löst sich in konzentrierter Schwefelsäure farblos, in Wasser mit blauvioletter Farbe. Er soll zum Färben von Acetatseide, acety- lierter Baumwolle und von Acetylcellulose- folien verwendet werden. Das Färbegut wird in der wässerigen Lösung in rotvioletten Tö nen gefärbt.
<I>Beispiel:</I> 100- kg Phenol werden mit 15 kg Form aldehyd von 40 Volumenprozent geschmol zen. Bei 40 C werden 20 kg 1,4-Diamino- 2-methylanthrachinon eingetragen und 4 Stun den weiter gerührt. Die Schmelze wird nun in 1.000 Liter Wasser gedrückt, das 50 kg Natriumchlorid und 45 kg Natriumhydrogyd gelöst enthält. Das ausgefallene Kondensa tionsprodukt wird abfiltriert, in Wasser auf genommen und mit Schwefelsäure neutral gestellt. Man filtriert, wäscht und trocknet.
Durch Sulfonieren bei 20' C in Schwefel säuremonohydrat erhält man einen Farbstoff, der sich in konzentrierter Schwefelsäure farblos, in Wasser mit blauvioletter Farbe löst. Er soll zum Färben von Acetatseide, acetylierter Baumwolle und von Acetyl- cellulosefolien verwendet werden. Das Färbe gut wird in der wässerigen Lösung in rot violetten Tönen: gefärbt.
Terfahren for the representation of a new, water-soluble dye of the anthraquinone series. The present patent relates to a process for the preparation of a new, water-soluble dye of the anthraquinone series and is characterized in that 1 mol of 1,4-diamino-2-methylanthraquinone, 1 mol of phenol and 1 mol of formaldehyde are allowed to act on each other and that product obtained sulfonated.
The new dye contains 1 sulfo group and dissolves in concentrated sulfuric acid colorless, in water with a blue-violet color. It is said to be used for dyeing acetate silk, acetylated cotton and acetyl cellulose foils. The dyed material is dyed in the aqueous solution in red-violet tones.
<I> Example: </I> 100 kg phenol are melted with 15 kg formaldehyde of 40 volume percent. At 40 ° C., 20 kg of 1,4-diamino-2-methylanthraquinone are added and the mixture is stirred for a further 4 hours. The melt is then pressed into 1,000 liters of water containing 50 kg of sodium chloride and 45 kg of sodium hydrogen in solution. The precipitated condensation product is filtered off, taken up in water and made neutral with sulfuric acid. It is filtered, washed and dried.
By sulfonating at 20 ° C. in sulfuric acid monohydrate, a dye is obtained which dissolves colorless in concentrated sulfuric acid and a blue-violet color in water. It is said to be used for dyeing acetate silk, acetylated cotton and acetyl cellulose films. The dyeing well is colored in an aqueous solution in red-violet shades:.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536303X | 1938-12-19 | ||
| CH224875T | 1939-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224875A true CH224875A (en) | 1942-12-15 |
Family
ID=25726800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224875D CH224875A (en) | 1938-12-19 | 1939-04-22 | Process for the preparation of a new, water-soluble dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH224875A (en) |
-
1939
- 1939-04-22 CH CH224875D patent/CH224875A/en unknown
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