CH187435A - Process for the production of a new anthraquinone dye. - Google Patents
Process for the production of a new anthraquinone dye.Info
- Publication number
- CH187435A CH187435A CH187435DA CH187435A CH 187435 A CH187435 A CH 187435A CH 187435D A CH187435D A CH 187435DA CH 187435 A CH187435 A CH 187435A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfuric acid
- amino
- dye
- anthraquinone
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000001000 anthraquinone dye Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 239000000975 dye Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 241000974482 Aricia saepiolus Species 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 3
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- -1 bromine compound Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Ilerstellung eines neuen Anthrachinonfarbstoffes. Gemäss der Erfindung erhält man einen neuen Anthrachinonfarbstoff, die 1-Amino 4-(4'-,dodecylsulfoanilide)ant*hrao'hinon-2-sul- fosäure, wenn man 2-Halogen-l-amino-4-(4- dodecylanilido)anthrap,hinon, (zum Beispiel die 2-Chlor oder Bromverbinclung) Schwefel säure und ein lösliches Sulfit aufeinander einwirken lässt.
Die Behandlung mit Schwefelsäure kann entweder vor oder nach dem Behandeln mit dem löslichen Sulfit ausgeführt wer-den.
Der Farbstoff löst sich in kaltem Wm- ser mit blauer Farbe und in Schwefelsäure mit heller, grünlichblauer Farbe. Er färbt Wolle aus einem neutralen oder sauren Bade in rein blauen Tönen von guter Haltbarkeit beim Waschen und Walken.
<I>Beispiel<B>1:</B></I> <B>10</B> Teile 2-Brom-l-amino-4-(9-,dodecyl- anilido)anthrachinon (welches erhalten wird durch Behandlung von<B>1</B> :3-Dibrom-4-amino- anthrachinon mit p-Dodecylanilin, welches wiederum hergestellt wer-den kann analog dem durch Beran benutzten Verfahren für p-Oetylanilin, Ber. der deutschen chem. Ges.
<B>1885, 18, 132)</B> werden in 40 Teilen Phenol gelöst und die Lösung miteiner Lösung von <B>50</B> Teilen kristallinisellem Natriumsulfit in <B>75</B> Teilen Wasser gemischt.
Das Gemisch wird während<B>8</B> Stunden unter Druck auf<B>170</B> bis<B>175 ' C</B> erhitzt und das Phenol dann,durch Wasserdampfdestilla- tion entfernt. Der Farbstoff, welcher eine sulzartige Form hat, wird durch Zusetzen von Salz zum Gerinnen gebracht, filtriert, getrocknet und gemahlen.
Der gemablene F arbstoff wird mit kaltem Benzin extralliert, um die benzinlöslichen Unreinigkeiten zu entfernen und schliesslich, wenn wünschbar,' einer weiteren Reinigung unterworfen, dureli Behandlung einer heissen, wässerigen Lösung des Farbstoffes mit aktiver Kohle" filtriert und mit Salz wieder ausgefällt.
<B>10</B> Teile dieses Produktes werden in<B>10,0</B> Teilen einer Iffligen Schwefelsäure von 2:5 <B>' C</B> gelöst, 20 Teile von<B>2,5 %</B> igem Oleum werden zugesetzt und das Gemisch während einer Stunde auf 2,5 bis<B>301 C</B> gehalten. Die Mischung wird dann in Eis gegossen und nachher filtriert. Das Ausgefällte wird in warmem Wasser gelöst, mit kaustischer Sodalösung alkalisch gemacht und ausge- salzen. Der gefällte Farbstoff wird filtriert, mit schwacher Salzlösung gewaschen und ge trocknet.
<I>Beispiel 2:</I> <B>10</B> Teile 2-Brem-l-amino-4-(4'-#dodeeyl- anilido)anthrachinon werden in<B>100</B> Teilen einer 100-%igen Schwefelsäure von 20 bis <B>2 2 5 '</B> C gelöst. 10 Teile Oleum (25 % SO.,) werden zugegeben<B>-und</B> die Mischung wird umgerührt, bis eine einem Gemisch von Ben zol und Wasser zugesetzte, Probe die Benzol- schielit nicht mehr färbt.
Wenn die Sulio- nation vollendet ist, wird die Schwefelsäure- lösung in Eis und Wasser gegossen und die Fällung wird filtriert und von Säure frei gewaschen. Der Filterkuphen wird alsdann mit verdünnter kaustiseher Soda gemahlen, das Produkt filtriert, mit Wasser gewaschen und getrocknet.
<B>10</B> Teile dieses Produktes,<B>180</B> TeilpWas- ser, <B>10</B> Teile kristallisiertes Natriumsulfit und<B>60</B> Teile Pyridin wer-den während 12 Stunden unter Druck auf<B>130</B> bis<B>185 '<I>C</I></B> erhitzt. Das Pyridin wird durch Wasser- dampfdestillation entfernt und die blaue Lö sung des Farbstoffes mit ein wenig aktiver Kohle gekocht, dann filtriert und, wenn er- kaltet, das Produkt mit Salz gefällt.
Dieses wird filtriert, mit schwacher Salzlösung ge waschen und getrocknet.
Process for the preparation of a new anthraquinone dye. According to the invention, a new anthraquinone dye is obtained, the 1-amino 4- (4 '-, dodecylsulfoanilide) ant * hrao'hinon-2-sulphonic acid, if 2-halo-1-amino-4- (4-dodecylanilido ) anthrap, hinon, (for example the 2-chlorine or bromine compound) allows sulfuric acid and a soluble sulfite to interact.
The treatment with sulfuric acid can be carried out either before or after the treatment with the soluble sulfite.
The dye dissolves in cold water with a blue color and in sulfuric acid with a light, greenish-blue color. It dyes wool from a neutral or acidic bath in pure blue shades that are durable to washing and fulling.
<I>Example<B>1:</B> </I> <B> 10 </B> parts of 2-bromo-1-amino-4- (9-, dodecyl-anilido) anthraquinone (which is obtained by Treatment of <B> 1 </B>: 3-dibromo-4-amino-anthraquinone with p-dodecylaniline, which in turn can be produced analogously to the process used by Beran for p-ethylaniline, Ber. Der Deutschen chem. Ges .
<B> 1885, 18, 132) </B> are dissolved in 40 parts of phenol and the solution is mixed with a solution of <B> 50 </B> parts of crystalline sodium sulfite in <B> 75 </B> parts of water.
The mixture is heated under pressure to <B> 170 </B> to <B> 175 ° C </B> for 8 hours and the phenol is then removed by steam distillation. The dye, which has a sultry shape, is made to curdle by adding salt, filtered, dried and ground.
The shaped dye is extruded with cold gasoline to remove the gasoline-soluble impurities and finally, if desired, subjected to further purification, filtered by treatment of a hot, aqueous solution of the dye with active charcoal and precipitated again with salt.
<B> 10 </B> parts of this product are dissolved in <B> 10.0 </B> parts of an ifligenic sulfuric acid of 2: 5 <B> 'C </B>, 20 parts of <B> 2, 5% oleum is added and the mixture is kept at 2.5 to 301 ° C. for one hour. The mixture is then poured into ice and then filtered. The precipitated material is dissolved in warm water, made alkaline with a caustic soda solution and salted out. The precipitated dye is filtered, washed with weak brine and dried.
<I> Example 2: </I> <B> 10 </B> parts of 2-Brem-l-amino-4- (4 '- # dodeeyl- anilido) anthraquinone are in <B> 100 </B> parts a 100% sulfuric acid of 20 to <B> 2 2 5 '</B> C dissolved. 10 parts of oleum (25% SO.) Are added and the mixture is stirred until a sample added to a mixture of benzene and water no longer stains the benzene schielite.
When the sulphonation is complete, the sulfuric acid solution is poured into ice and water and the precipitate is filtered and washed free of acid. The filter cup is then ground with dilute caustic soda, the product filtered, washed with water and dried.
<B> 10 </B> parts of this product, <B> 180 </B> parts of water, <B> 10 </B> parts of crystallized sodium sulfite and <B> 60 </B> parts of pyridine become during Heated for 12 hours under pressure to <B> 130 </B> to <B> 185 '<I> C </I> </B>. The pyridine is removed by steam distillation and the blue solution of the dye is boiled with a little active charcoal, then filtered and, when cooled, the product is precipitated with salt.
This is filtered, washed with weak salt solution and dried.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH187435T | 1935-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH187435A true CH187435A (en) | 1936-11-15 |
Family
ID=4435015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH187435D CH187435A (en) | 1935-07-15 | 1935-07-15 | Process for the production of a new anthraquinone dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH187435A (en) |
-
1935
- 1935-07-15 CH CH187435D patent/CH187435A/en unknown
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