CH152509A - Process for the preparation of a dye of the anthraquinone series. - Google Patents
Process for the preparation of a dye of the anthraquinone series.Info
- Publication number
- CH152509A CH152509A CH152509DA CH152509A CH 152509 A CH152509 A CH 152509A CH 152509D A CH152509D A CH 152509DA CH 152509 A CH152509 A CH 152509A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- blue
- acid
- gray
- preparation
- Prior art date
Links
- 238000000034 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
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005749 Copper compound Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
- PZKPUGIOJKNRQZ-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,3-diamine Chemical group CC1(N)CC(N)=CC=C1 PZKPUGIOJKNRQZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UASJEBYKRVLBPP-UHFFFAOYSA-N NC1=C(C=C(C=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O)Br)Br Chemical compound NC1=C(C=C(C=2C(C=3C(=CC=CC3C(C12)=O)S(=O)(=O)O)=O)Br)Br UASJEBYKRVLBPP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Coloring (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Darstellung eines Farbsto-ffes der Anthrachinonreihe. Das vorliegende Verfahren betrifft die Dar stellung eines grauen Farbstoffes der Anthra- chinonreihe, darin bestehend, dass man ein Salz der 1-Amino-2,4-dibromanthrachinon-5- sulfosäure mit m-Toluylendiamin in Gegen wart von Kupferverbindungen und säurebin denden Mitteln kondensiert und die erhaltene Farbstoffbase so lange mit Sulfit behandelt,
bis das P-ständige. Bromatom vollständig durch eine Suliogruppe ersetzt wird. <I>Beispiel:</I> 20 Teile 1-amino-2,4'dibromaiithrachinon- 5-sulfosa(ires Kalium werden mit<B>300</B> Teilen Wasser,<B>5</B> Teilen wasserfreiem Natriumear- bonat, <B>3</B> Teilen kristallisiertem Kupfersulfat und<B>10</B> Teilen m-ToluyIendiamin in einer in differenten Atmosphäre auf<B>60-70 0</B> C so lange erhitzt,bis das Bromatom in 4-Stellung vollstän dig durch den m-Toluylendiaminrest ersetzt ist.
Die entstandene Farbsto<B>ff</B> sulfosäure wird durch Ansäuern gefällt und so lange mit Kalium- sulfit erhitzt, bis das Bromatom in 2-Stellung durch eine Sulfogruppe vollständig ersetzt wird. Der entstandene Farbstoff wird durch Aussalzen aus der Lösung isoliert.
Er besitzt die Formel
EMI0001.0029
und stellt in trockenem Zustande ein blau schwarzes Pulver dar, welches in Wasser mit blauer Farbe, in konzentrierter Schwefelsäure mit bräunlichroter Farbe, welche auf Zusatz von Borsäure schmutzig grünblau wird, löslich ist. In kaltem Äthylalkohol ist er mit blauer Farbe schwer löslich. Er färbt ungebeizte Wolle aus saurem Bade in bläulichgrauen Tönen an, welche durch Chromieren in Grau übergehen.
Process for the preparation of a dye of the anthraquinone series. The present process relates to the presentation of a gray dye of the anthrachinone series, consisting in that a salt of 1-amino-2,4-dibromoanthraquinone-5-sulfonic acid is condensed with m-toluenediamine in the presence of copper compounds and acid-binding agents and the dye base obtained is treated with sulfite for so long
until the P-permanent. The bromine atom is completely replaced by a sulio group. <I> Example: </I> 20 parts 1-amino-2,4'dibromaiithraquinone- 5-sulfosa (ires potassium are mixed with <B> 300 </B> parts of water, <B> 5 </B> parts of anhydrous Sodium carbonate, <B> 3 </B> parts of crystallized copper sulfate and <B> 10 </B> parts of m-toluene diamine in a different atmosphere heated to <B> 60-70 0 </B> C for so long until the bromine atom in the 4-position is completely replaced by the m-toluenediamine residue.
The resulting dye sulfonic acid is precipitated by acidification and heated with potassium sulfite until the bromine atom in the 2-position is completely replaced by a sulfo group. The resulting dye is isolated from the solution by salting out.
He owns the formula
EMI0001.0029
and when dry it is a blue-black powder which is soluble in water with a blue color, in concentrated sulfuric acid with a brownish-red color, which becomes dirty green-blue on the addition of boric acid. In cold ethyl alcohol it is poorly soluble with a blue color. He dyes unstained wool from an acid bath in bluish-gray tones, which change to gray through chroming.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE152509X | 1929-10-04 | ||
| CH149419T | 1930-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH152509A true CH152509A (en) | 1932-01-31 |
Family
ID=25715432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH152509D CH152509A (en) | 1929-10-04 | 1930-09-27 | Process for the preparation of a dye of the anthraquinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH152509A (en) |
-
1930
- 1930-09-27 CH CH152509D patent/CH152509A/en unknown
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