CH224876A - 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
- CH224876A CH224876A CH224876DA CH224876A CH 224876 A CH224876 A CH 224876A CH 224876D A CH224876D A CH 224876DA CH 224876 A CH224876 A CH 224876A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- new
- preparation
- soluble dye
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 3
- 150000004056 anthraquinones Chemical class 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
- 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
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 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
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 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
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/542—Anthraquinones with aliphatic, cycloaliphatic, araliphatic or aromatic ether groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Zusatzpatent zum Hauptpatent Xr. 210608. Verfahren zur Darstellung eines neuen, wasserlöslichen Farbstoffes der Antlirachinonr eihe. 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-methoxyanthraehinon, 1 Mol Phenol und 1 Mol Formaldehyd auf einander einwirken lässt und das erhaltene Produkt sulfoniert.
Der neue Farbstoff enthält eine Sulfo- gruppe, löst sich in konzentrierter Schwefel säure mit schwach rötlicher, in Wasser mit rotvioletter Farbe. Er soll zum Färben von Acetatseide, acetylierter Baumwolle und von Acetyleellulosefolien verwendet werden. Das Färbegut wird in der wässerigen Lösung in rosa Tönen gefärbt. Beispiel: 100 kg Phenol werden mit 15 kg Form aldehyd von 40 Volumenprozent geschmol zen.
Bei 40 C werden 20 kg 1,4-Diamino- 2 - methoxyanthrachinon eingetragen und 4 Stunden weiter gerührt. Die Schmelze wird nun in 1000 Liter Wasser gedrückt, das 50 kg Natriumchlorid und 45 kg Natrium hydroxyd gelöst enthält. Das ausgefallene Kondensationsprodukt wirdätfiltiiert, in Wasser aufgenommen und mit Schwefel säure neutral gestellt. Man ,filtriert, wäscht und trocknet. _ Durch Sulfonieren bei 20' C in Schwefel säuremonohydrat erhält man einen Farb stoff, der sich in konzentrierter Schwefel säure mit schwach rötlicher, in Wasser mit rotvioletter Farbe löst.
Er soll zum Färben von Acetatseide, acetylierter Baumwolle und von Acetylcellulosefolien verwendet werden. Das Färbegut wird in der wässerigen Lö sung in rosa Tönen gefärbt.
Additional patent to the main patent Xr. 210608. Process for the preparation of a new, water-soluble dye of the antlirachinone 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 mole of 1,4-diamino-2-methoxyanthraehinone, 1 mole of phenol and 1 mole of formaldehyde are allowed to act on each other and the result is Sulfonated product.
The new dye contains a sulfo group, dissolves in concentrated sulfuric acid with a slightly reddish color, in water with a red-violet color. It is said to be used for dyeing acetate silk, acetylated cotton and acetyl cellulose films. The dyed material is dyed in pink tones in the aqueous solution. Example: 100 kg of phenol are melted with 15 kg of formaldehyde of 40 percent by volume.
At 40 ° C., 20 kg of 1,4-diamino-2-methoxyanthraquinone are added and the mixture is stirred for a further 4 hours. The melt is then pressed into 1000 liters of water containing 50 kg of sodium chloride and 45 kg of sodium hydroxide 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 in concentrated sulfuric acid with a slightly reddish color and in water with a red-violet color.
It is said to be used for dyeing acetate silk, acetylated cotton and acetyl cellulose films. The material to be dyed is dyed in pink tones in the aqueous solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536303X | 1938-12-19 | ||
| CH224876T | 1939-04-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH224876A true CH224876A (en) | 1942-12-15 |
Family
ID=25726801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH224876D CH224876A (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) | CH224876A (en) |
-
1939
- 1939-04-22 CH CH224876D patent/CH224876A/en unknown
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