AT158864B - Process for the preparation of water-soluble dyes for cellulose esters and ethers and processes for dyeing and printing cellulose esters and ethers. - Google Patents
Process for the preparation of water-soluble dyes for cellulose esters and ethers and processes for dyeing and printing cellulose esters and ethers.Info
- Publication number
- AT158864B AT158864B AT158864DA AT158864B AT 158864 B AT158864 B AT 158864B AT 158864D A AT158864D A AT 158864DA AT 158864 B AT158864 B AT 158864B
- Authority
- AT
- Austria
- Prior art keywords
- ethers
- cellulose esters
- water
- dyeing
- preparation
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- 229920002678 cellulose Polymers 0.000 title claims description 4
- 229920003086 cellulose ether Polymers 0.000 title claims description 4
- 150000002170 ethers Chemical class 0.000 title claims description 4
- 238000004043 dyeing Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- -1 sodium n-butylanilino-thiosulphonic acid Chemical compound 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 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 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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wird in einer der gewünschten Farbtiefe entsprechenden Menge (etwa 2% vom Gewicht des Färbegutes) in wässeriger Lösung unter Zusatz von etwa 20% Kochsalz (berechnet auf das Gewicht des Färbegutes) auf das zu färbende Acetatseidengewebe bei einem Flottenverhältnis 1 : 30 unter Erwärmen auf
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schaften.
Man kann mit dem gleichen Ergebnis auch nach andern für wasserlösliche Acetatseidenfarbstoffe üblichen Verfahren, beispielsweise in schwach sauren oder andern salzhaltigen Bädern, z. B. unter Zusatz von Glaubersalz usw., färben.
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Beispiel 3. SO Gewichtsteile des durch Kuppeln von diazotiertem o-Nitranilin mit N-butylanilino-thiosulfonsauren Natrium (dargestellt wie im Beispiel 1 angegeben) erhaltenen Azofarbstoffes der Konstitution
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erhält einen schonen orangefarbenen Druck von guten Echtheitseigenschaften.
Beispiel 4. Ein Aeetatseidenkreppgewebe wird nach der im Beispiel 1 angegebenen Farbemethode mit dem durch Kuppeln von diazotiertem p-Nitranilin mit N-butyl-toluidino-äthan-thioessigsaurem Natrium dargestellten Farbstoff der Konstitution
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gefärbt. Man erhalt eine schone blaustichig rote, gut durchgefärbte weiss ätzbare Ausfärbung mit guten Echtheitseigenschaften.
Das Toludino-thioessigsäurederivat kann auf folgendem Wege dargestellt werden : 130 Gewichtsteile N- (ButyI-3-chIoräthyI)-m-toluidin werden in 400 Volumteilen Äthylalkohol mit CO Gewichtsteilen Merkaptoessigsäure (gelost in 100 Volumteilen Wasser und 52'2 Gewichtsteilen Ätznatron) unter Rühren auf 80 C erwärmt, bis eine zur Trockne gedampfte Probe wasserlöslich geworden ist.
Dann wird der ganze Ansatz durch Eindunsten im Vakuum vom Lösungsmittel befreit, der Rückstand in heissem Wasser aufgenommen und das Reaktionsprodukt durch Zusatz von etwas
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anthrachinon erhältliche wasserlösliche Farbstoff der vermutlichen Konstitution
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wird nach Beispiel 1 zum Färben eines Aeetatseidengewebes verwandt. Man erhält eine schiene rotstichig blaue Färbung.
Die Unsetzung mit Thiosulfat geschicht auf folgende Weise : 100 Gewichtsteile N,N'-(γ-Chlor-ss-propyl)-1,4-diaminoanthrachinon werden in 1000 Gewiehtsteilen Äthylalkohol mit 62 Gewichtsteilen Natrinmthiosulfat in 500 Gewichtsteilen Wasser mehrstündig auf 80 C erhitzt,
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bis eine eingedampfte Probe wasserlöslich geworden ist. Dann wird die Gesamtmenge vom Lösungmittel befreit, der Rückstand in Wasser aufgenommen, von kleinen Verunreinigungen durch Filtrieren getrennt und durch Aussalzen abgeschieden.
Beispiel 6. Der durch Umsetzung des Kondensatorproduktes aus N- (ss-Chloräthyl-butyl)- p-aminobenzaldehyd und Cyanessigester mit Thiosulfat erhaltene Farbstoff der Konstitution
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Acetatseidengewebes.
Beispiel 7. Man färbt nach der im Beispiel 1 angegebenen Methode ein Aeetatseidengewebe
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und erhält eine grünstichig gelbe Färbung von guter Affinität.
PATENT-ANSPRÜCHE :
1. Verfahren zur Herstellung wasserlöslicher Farbstoffe für Celluloseester und-äther, dadurch
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is applied in an amount corresponding to the desired depth of color (about 2% of the weight of the material to be dyed) in an aqueous solution with the addition of about 20% table salt (calculated on the weight of the material to be dyed) on the acetate silk fabric to be dyed at a liquor ratio of 1:30 with heating
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properties.
The same result can also be used by other methods customary for water-soluble acetate silk dyes, for example in weakly acidic or other saline baths, e.g. B. with the addition of Glauber's salt, etc., color.
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Example 3. 50 parts by weight of the azo dye of the constitution obtained by coupling diazotized o-nitroaniline with sodium n-butylanilino-thiosulphonic acid (shown as indicated in Example 1)
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receives a beautiful orange-colored print with good fastness properties.
Example 4. An acetate silk crepe fabric is made according to the color method given in Example 1 with the dye of constitution represented by coupling diazotized p-nitroaniline with sodium N-butyl-toluidino-ethane-thioacetate
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colored. A beautiful bluish red, well-colored, white-etchable coloration with good fastness properties is obtained.
The toludino-thioacetic acid derivative can be prepared in the following way: 130 parts by weight of N- (butyl-3-chloroethyl) -m-toluidine are mixed in 400 parts by volume of ethyl alcohol with CO parts by weight of mercaptoacetic acid (dissolved in 100 parts by volume of water and 52'2 parts by weight of caustic soda) with stirring heated to 80 C until a sample evaporated to dryness has become water-soluble.
The whole batch is then freed from the solvent by evaporation in vacuo, the residue is taken up in hot water and the reaction product is added by adding something
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Anthraquinone available water-soluble dye of the presumed constitution
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is used according to Example 1 for dyeing an acetate silk fabric. A reddish-tinged blue color is obtained.
The reaction with thiosulphate is as follows: 100 parts by weight of N, N '- (γ-chloro-ss-propyl) -1,4-diaminoanthraquinone in 1000 parts by weight of ethyl alcohol with 62 parts by weight of sodium thiosulphate in 500 parts by weight of water are heated to 80 ° C. for several hours ,
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until an evaporated sample has become water-soluble. Then the entire amount is freed from the solvent, the residue is taken up in water, separated from small impurities by filtration and deposited by salting out.
Example 6. The constitutional dye obtained by reacting the capacitor product from N- (s-chloroethyl-butyl) -p-aminobenzaldehyde and cyanoacetic ester with thiosulphate
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Acetate silk fabric.
Example 7. An acetate silk fabric is dyed according to the method given in Example 1
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and has a greenish yellow coloration with good affinity.
PATENT CLAIMS:
1. Process for the preparation of water-soluble dyes for cellulose esters and ethers, thereby
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Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT158864T | 1938-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT158864B true AT158864B (en) | 1940-06-10 |
Family
ID=3650052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT158864D AT158864B (en) | 1938-05-14 | 1938-05-14 | Process for the preparation of water-soluble dyes for cellulose esters and ethers and processes for dyeing and printing cellulose esters and ethers. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT158864B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226395A (en) * | 1960-10-04 | 1965-12-28 | Hoechst Ag | Water-insoluble phthalocyanine dyestuffs and process for their manufacture |
-
1938
- 1938-05-14 AT AT158864D patent/AT158864B/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226395A (en) * | 1960-10-04 | 1965-12-28 | Hoechst Ag | Water-insoluble phthalocyanine dyestuffs and process for their manufacture |
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