DE593572C - Process for the production of gray dyes of the anthraquinone series - Google Patents
Process for the production of gray dyes of the anthraquinone seriesInfo
- Publication number
- DE593572C DE593572C DEC44094D DEC0044094D DE593572C DE 593572 C DE593572 C DE 593572C DE C44094 D DEC44094 D DE C44094D DE C0044094 D DEC0044094 D DE C0044094D DE 593572 C DE593572 C DE 593572C
- Authority
- DE
- Germany
- Prior art keywords
- gray
- dyes
- production
- anthraquinone series
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 title claims description 13
- 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
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical group [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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 Herstellung von grauen Farbstoffen der Anthrachinonreihe Aus dem Hauptpatent 578.415 ist zu entnehmen, daß die Farbstoffe der allgemeinen Formel worin X Halogen oder S03 H und Y Wasserstoff oder S03H bedeuten, Wolle in saurem Bade in grauen, blaugrauen bis grüngrauen Tönen von hervorragender Echtheit anfärben und nachchromiert werden können.Process for the preparation of gray dyes of the anthraquinone series From the main patent 578.415 it can be seen that the dyes of the general formula where X is halogen or SO3 H and Y is hydrogen or SO3H, wool can be dyed in an acid bath in gray, blue-gray to green-gray shades of excellent fastness and can be re-chromed.
Es wurde nun weiter gefunden, daß, wenn man. an Stelle der Phenylendiamine des Hauptpatents Naphthylendiamine verwendet, man ähnliche neue wertvolle Farbstoffe erhält, welche Wolle in saurem Bade ebenfalls in grauen Tönen von hervorragender Echtheit anfärben. Auch diese Färbungen besitzen die Eigenschaft, durch Nachbehandlung mit Chromaten oder Bichromaten unter mehr oder weniger ausgeprägter Nuancenverschiebung in grüngraue bis braungraue Töne überzugehen. Einzelne der neuen Farbstoffe sind ferner vorzüglich zum Färben von chargierter Naturseide in neutralem Bade geeignet.It has now been further found that if one. instead of the phenylenediamines of the main patent naphthylenediamines, one uses similar new valuable dyes receives, which wool in acid baths is also excellent in gray tones Color authenticity. These colorations also have the property of after-treatment with chromates or bichromates with a more or less pronounced shift in nuances to change into green-gray to brown-gray tones. Some of the new dyes are also particularly suitable for dyeing charged natural silk in neutral baths.
Die neuen Farbstoffe können in der Weise hergestellt werden, daß man i-Amino-2, 4-dihalogenanthrachinone oder i-Amino-4-halogenanthrachinon-2-sulfonsäuren, welche im zweiten Benzolkern des Anthrachinonmoleküls eine S03H-Gruppe enthalten, mit Naphthylendiaminen, z. B. i, 5-Naphthylendiamin, und Kupfer oder Kupferverbindungen bei Gegenwart von säurebindenden Mitteln erhitzt und die entstandenen wohlcharakterisierten Verbindungen gegebenenfalls in bekannter Weise sulfoniert.The new dyes can be prepared in such a way that one i-Amino-2, 4-dihalogenanthraquinones or i-amino-4-halogenanthraquinone-2-sulfonic acids, which contain an S03H group in the second benzene nucleus of the anthraquinone molecule, with naphthylenediamines, e.g. B. i, 5-naphthylenediamine, and copper or copper compounds heated in the presence of acid-binding agents and the resulting well-characterized Compounds optionally sulfonated in a known manner.
Beispiel i 2o Teile. i-amino-2, 4-dibrom-8-anthrachinonsulfönsaures Kalium werden auf dem Wasserbade in einer indifferenten Atmosphäre mit 15 Teilen i, 5-Naphthylendiamin, 5 Teilen calciniertem Natriumcarbonat, 3 Teilen Kupfervitriol und 3oo Teilen Wasser während 5 bis 6 Stunden auf 95 bis 98' C erhitzt. Die entstandene Masse wird dann in 3ooo Teile angesäuertes `Wasser eingerührt und die ausgeschiedene Monosulfonsäure filtriert und gewaschen. Diese wird nun weiter mit Alkalisulfit in Gegenwart von Wasser und Phenol so lange unter Druck erhitzt, bis das in 2-Stellung befindliche Bromatom durch die Sulfonsäuregruppe ersetzt ist. Darauf bläst man das Phenol mit Dampf ab und salzt den Farbstoff aus. Er färbt Wolle in saurem Bade in grauen Tönen, welche durch Nachchromieren grünlichgrau werden. Die Färbungen besitzen ausgezeichnete Echtheitseigenschaften.Example i 2o parts. Potassium i-amino-2, 4-dibromo-8-anthraquinonesulphonate is increased to 95 parts on a water bath in an inert atmosphere with 15 parts of i, 5-naphthylenediamine, 5 parts of calcined sodium carbonate, 3 parts of vitriol and 300 parts of water for 5 to 6 hours heated to 98 ° C. The resulting mass is then stirred into 3,000 parts of acidified water and the precipitated monosulfonic acid is filtered and washed. This is then further heated under pressure with alkali sulfite in the presence of water and phenol until the 2-position bromine atom has been replaced by the sulfonic acid group. The phenol is then blown off with steam and the dye is salted out. It dyes wool in an acidic bath in gray tones, which become greenish-gray when chromium plating. The dyeings have excellent fastness properties.
Beispiel 2 Ersetzt man das im Beispiel 1 verwendete 1, 5-Naphthylendiamin durch 15 Teile 1, 8-Naphthylendiamin, so erhält man nach gleicher Arbeitsweise einen Farbstoff,- welcher Wolle in saurem Bade in grauen Tönen färbt, welche durch Nachchromieren braungrau werden. Die Echtheit dieser Färbungen ist ausgezeichnet. Der Farbstoff besitzt ferner sehr gute Affinität für chargierte Naturseide und färbt diese in neutralem Bade grau.Example 2 The 1,5-naphthylenediamine used in Example 1 is replaced by 15 parts of 1,8-naphthylenediamine, one obtains a by the same procedure Dye - which dyes wool in an acid bath in gray tones, which by re-chroming turn brown-gray. The fastness of these dyeings is excellent. The dye also has a very good affinity for charged natural silk and dyes it in neutral bath gray.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC44094D DE593572C (en) | 1929-12-08 | 1929-12-08 | Process for the production of gray dyes of the anthraquinone series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC44094D DE593572C (en) | 1929-12-08 | 1929-12-08 | Process for the production of gray dyes of the anthraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE593572C true DE593572C (en) | 1934-03-03 |
Family
ID=7025666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC44094D Expired DE593572C (en) | 1929-12-08 | 1929-12-08 | Process for the production of gray dyes of the anthraquinone series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE593572C (en) |
-
1929
- 1929-12-08 DE DEC44094D patent/DE593572C/en not_active Expired
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