CH301344A - Process for the preparation of a sulfonic acid amide of the anthraquinone series. - Google Patents
Process for the preparation of a sulfonic acid amide of the anthraquinone series.Info
- Publication number
- CH301344A CH301344A CH301344DA CH301344A CH 301344 A CH301344 A CH 301344A CH 301344D A CH301344D A CH 301344DA CH 301344 A CH301344 A CH 301344A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- acid amide
- anthraquinone series
- preparation
- parts
- 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 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 238000009941 weaving Methods 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- DQJOVACPLUONOS-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=2C(C3=CC(=C(C=C3C(C1=2)=O)Cl)Cl)=O Chemical compound C1(=CC=CC=C1)NC1=CC=CC=2C(C3=CC(=C(C=C3C(C1=2)=O)Cl)Cl)=O DQJOVACPLUONOS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Woven Fabrics (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 297845. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Sulfon- sä.ureamides der Anthrachinonreihe, welches darin besteht, dass man 1 Mol des nach der Schweizer Patentschrift Nr.
295893 erhältli- ehen 1,4-Di - (2',6'-dimethyl) - phenyla,mino- 6, 7-diehloranthrachinondisulfonsäurechlorides mit 2 --Hol 2-Aminoäthan-l-sulfonsäure kon densiert.
Im nachfolgenden Beispiel bedeuten die Teile Gewichtsteile.
<I>Beispiel:</I> Man verrührt eine feuchte Paste des nach (len Angaben der Schweizer Patentschrift Nr.295893 aus<B>51,5</B> Teilen 1,4-Di-(2',6'-dime- tliyl)-phenylamino-6,7-dichloranthra.chinon er hältlichen Disulfonsäurechlorides mit 180 Tei len einer 200/eigen Lösung aus 2-aminoät.han- 1-sulfonsaurem Natrium.
Nach Zugabe von 20 Teilen Natriumbicarbonat und 1.00 Teilen 80o/oigem Isopropylalkohol rührt man die Kondensationsmasse 3 Stunden lang bei 50 . Dabei wird das Reaktionsgemisch wasserlös lich. Nun rührt man die :Masse noch 2 Stun den lang bei 80 am Rückfluss, versetzt sie mit SO Teilen Natriumehlorid und rührt sie kalt.
Man filtriert das gebildete Kondensationspro- dukt ab, wäscht es mit 10o/oiger Natriumchlo- ridlösung neutral und trocknet es.
Das neue Sulfonsäureamid der Anthrachi- nonreihe löst sich in Wasser und in konzen trierter Schwefelsäure mit blauer Farbe und färbt Wolle, Seide, Tussah und synthetische Polyamidfasern in blauen Tönen von sehr guter Walk- und Lichtechtheit.
Additional patent to the main patent no. 297845. The subject of the present patent is a process for the preparation of a sulfonic acidic acid amide of the anthraquinone series, which consists in adding 1 mol of the substance described in Swiss patent no.
295893 obtainable 1,4-di- (2 ', 6'-dimethyl) - phenyla, mino- 6, 7-diehloranthraquinone disulfonic acid chlorides condensed with 2 -Hol 2-aminoethane-1-sulfonic acid.
In the following example, the parts are parts by weight.
<I> Example: </I> A moist paste of the (len information of Swiss patent specification No. 295893 from <B> 51.5 </B> parts of 1,4-di- (2 ', 6'- Dimethyl) phenylamino-6,7-dichloranthraquinone available disulfonic acid chlorides with 180 parts of a 200 / own solution of 2-aminoät.han- 1-sulfonic acid sodium.
After addition of 20 parts of sodium bicarbonate and 1.00 part of 80% isopropyl alcohol, the condensation mass is stirred for 3 hours at 50. The reaction mixture becomes water-soluble. The mass is now stirred for 2 hours at 80 reflux, 50 parts of sodium chloride are added to it and it is stirred cold.
The condensation product formed is filtered off, washed neutral with 10% sodium chloride solution and dried.
The new sulphonic acid amide of the anthraquinone series dissolves in water and in concentrated sulfuric acid with a blue color and dyes wool, silk, tussah and synthetic polyamide fibers in blue shades with very good fulling and lightfastness.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH297845T | 1951-10-18 | ||
| CH301344T | 1951-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH301344A true CH301344A (en) | 1954-08-31 |
Family
ID=25733900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH301344D CH301344A (en) | 1951-10-18 | 1951-10-18 | Process for the preparation of a sulfonic acid amide of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH301344A (en) |
-
1951
- 1951-10-18 CH CH301344D patent/CH301344A/en unknown
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