DE638833C - Process for the preparation of water-soluble dyes of the anthraquinone series - Google Patents
Process for the preparation of water-soluble dyes of the anthraquinone seriesInfo
- Publication number
- DE638833C DE638833C DEI49451D DEI0049451D DE638833C DE 638833 C DE638833 C DE 638833C DE I49451 D DEI49451 D DE I49451D DE I0049451 D DEI0049451 D DE I0049451D DE 638833 C DE638833 C DE 638833C
- Authority
- DE
- Germany
- Prior art keywords
- water
- preparation
- amino
- soluble dyes
- anthraquinone series
- 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 8
- 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 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 5
- -1 amino compound Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 210000002268 wool Anatomy 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000003381 solubilizing effect Effects 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
- C09B1/343—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von wasserlöslichen Farbstoffen der Anthrachinonreihe Es wurde gefunden, daß man wertvolle Farbstoffe der Anthrachinonreihe erhält, wenn man r-Amino-4-halogenanthrachinon-2-sulfonsäure mit einer keinen wasserlöslich machenden Substituenten enthaltenden Aminoverbindung der Benzolreihe, die in o-Stellung zur Aminogruppe einen organischen, die SO,- oder CO-Gruppe enthaltenden Substituenten und in Parastellung zu diesem Substituenten oder zur Amiinogruppe eine weitere primäre Aminogruppe trägt, kondensiert. Solche Aminoverbindungen sind z. B. 2 - 5-Diaminodiphenylsulfoii, 2 # 4-Diaminophenyltolylsulfon, 2 # 5 -Diaminophenylätliylsulfon, 2 # 5-Diamino-r-sulfodiäthy lamiclobenzol, 2 # 5-Diaminobenzolsulfopiperidid, 2 # 4-Diaminobenzolsulfosäureäthylester, 2 # 5-Diaminobenzoesäureamid oder allgemeiner solche, die sich von der allgemeinen Formel worin X oder Y - N H2, Z - C O oder S 0z und R, beispielsweise Alkyl, Arvl, Aralkyl, O-Alkyl, O-Aryl O-Aralkyl, N H2, N H-Alkyl, N H-Aryl, N (L?ialkyl), NH-Cycloalkyl (also primäre, sekundäre und tertiäre aliphatische oder aromatische Aminogruppen) sein kann und R noch weiter substituiert sein kann, wobei indessen löslichmachende Substituenten ausgenommen sein sollen ableiten. Die Umsetzung wird zweckmäßig in wäßrigem Medium mit oder ohne Zusatz eines wasserlöslichen organischen Lösungsmittels in Alkohol oder Pyridin bei erhöhter Temperatur und in Gegenwart eines säurebindenden Mittels, wie Soda, Bicarbonat u. dgl., und eines, geeigneten Katalysators, wie Kupfer oder seine Salze, durchgeführt.Process for the preparation of water-soluble dyes of the anthraquinone series It has been found that valuable dyes of the anthraquinone series are obtained if r-amino-4-halogenanthraquinone-2-sulfonic acid with an amino compound of the benzene series which does not contain any water-solubilizing substituents and which is in o-position to Amino group carries an organic substituent containing the SO, - or CO group and a further primary amino group in para position to this substituent or to the amino group. Such amino compounds are e.g. B. 2-5-Diaminodiphenylsulfoii, 2 # 4-Diaminophenyltolylsulfon, 2 # 5 -Diaminophenylätliylsulfon, 2 # 5-Diamino-r-sulfodiäthy lamiclobenzol, 2 # 5-Diaminobenzenesulfopiperidid, 2 # 4-Diaminobenzenesulfosäure, 2 # 4-Diaminobenzenesulfosäure, 2 # 4-Diaminobenzenesulfosäure, 2 # those that differ from the general formula where X or Y - N H2, Z - CO or S 0z and R, for example alkyl, Arvl, aralkyl, O-alkyl, O-aryl, O-aralkyl, N H2, N H-alkyl, N H-aryl, N ( L? Ialkyl), NH-cycloalkyl (that is, primary, secondary and tertiary aliphatic or aromatic amino groups) and R can be further substituted, although solubilizing substituents should be excluded. The reaction is expediently carried out in an aqueous medium with or without the addition of a water-soluble organic solvent in alcohol or pyridine at elevated temperature and in the presence of an acid-binding agent, such as soda, bicarbonate and the like, and a suitable catalyst, such as copper or its salts, carried out.
Die neuen Produkte sind wertvolle blaue Wollfarbstoffe von guten Echtheitseigenschaften und insbesondere guter Waschechtheit.The new products are valuable blue wool dyes with good fastness properties and especially good washfastness.
Beispiele z. ro Gewichtsteile i-Amino-4-bromanthrachinon-2-sulfonsäure werden mit 6,5 Gewichtsteilen 2 # 5-Diaminodiphenylsulfon, io Gewichtsteilen Natriumbicarbonat und -o,5 Gewichtsteilen Kupferchlorür in Gegenwart von Wasser einige Stunden im Sieden gehalten. Der in üblicher Weise isolierte Farbstoff der folgenden Konstitution: färbt Wolle aus sauren Bädern in grünstichigblauen Tönen von guter Licht-, Wasch- und Walkechtheit.Examples e.g. Ro parts by weight of i-amino-4-bromoanthraquinone-2-sulphonic acid are kept at the boil for a few hours in the presence of water with 6.5 parts by weight of 2 # 5-diaminodiphenyl sulphone, 10 parts by weight of sodium bicarbonate and 0.5 parts by weight of copper chloride. The dye of the following constitution, isolated in the usual way: dyes wool from acid baths in greenish blue shades of good lightfastness, washfastness and milled fastness.
2. Ersetzt man das in Beispiel i verwandte, 2 - 5-Diaminodiphenylsulfön durch 6 GA5` wichtsteile 2 - 5-Diaminobenzolsulfosäuret'@'`f' äthylamid, so erhält man den Farbstoff fq-. Bender Konstitution: dessen blaue Färbungen auf Wolle sich durch gute Licht- und Waschechtheit auszeichnen.2. If the 2 - 5-diaminodiphenyl sulfone used in Example i is replaced by 6 GA5 'parts by weight of 2 - 5-diaminobenzene sulfonic acid' @ '''f' ethylamide, the dye fq- is obtained. Bender constitution: whose blue dyeings on wool are characterized by good lightfastness and washfastness.
3. io Gewichtsteile i-Amino-4-bromanthrachinon-2-sulfosäure werden
zusammen mit
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI49451D DE638833C (en) | 1934-04-08 | 1934-04-08 | Process for the preparation of water-soluble dyes of the anthraquinone series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI49451D DE638833C (en) | 1934-04-08 | 1934-04-08 | Process for the preparation of water-soluble dyes of the anthraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE638833C true DE638833C (en) | 1936-11-23 |
Family
ID=7192580
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI49451D Expired DE638833C (en) | 1934-04-08 | 1934-04-08 | Process for the preparation of water-soluble dyes of the anthraquinone series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE638833C (en) |
-
1934
- 1934-04-08 DE DEI49451D patent/DE638833C/en not_active Expired
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